
# ol991194u.cif

data_global
_audit_creation_method           'SHELXL-97 and manual editing' 
#=======================================================================
# 1. MANUSCRIPT NUMBER
#
#    ID:OL991194U
#

# 2. SUBMISSION DETAILS

_publ_contact_author_name          'Dr Ivo Vencato' 
_publ_contact_author_address  
;
    Depto. Química - UFSC 
    88040 - 900 Florianópolis, SC 
    Brazil
;
_publ_contact_author_email         vencato@qmc.ufsc.br
_publ_contact_author_fax           '55(2148)3316888'    
_publ_contact_author_phone         '55(2148)3316826'  
_publ_contact_letter
; 
    Please consider this CIF as Supporting Information for 
    Organic Letters.   
;
_publ_requested_coeditor_name            ?
_publ_requested_journal             ' Organic Letters '

#=======================================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title
;
The Stereoselective Synthesis of Functionalized trans-2,5-Disubstituted
Tetrahydrofurans

;
loop_
_publ_author_name
_publ_author_address

    'Pilli, Ronaldo A.'
;    Instituto de Química - Unicamp 
     Cx. Postal 6154, 13083-970 - Campinas, SP 
     Brazil
;    

    'Riatto, Valéria B.'
;    Instituto de Química - Unicamp 
     Cx. Postal 6154, 13083-970 - Campinas, SP 
     Brazil
;    

    'Vencato, Ivo'
;    Depto. Química - UFSC
     88040-900 - Florianópolis, SC
     Brazil
;

#=======================================================================

;
_publ_section_references

;

Enraf-Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf-Nonius,  
        Delft, The Netherlands.

Fair, C. K. (1990). MolEN. An Interactive Intelligent System for 
        Crystal Structure Analysis. Enraf-Nonius, Delft, The 
        Netherlands.

Flack, H. D. (1983). Acta Cryst. A39, 876--881. 

Sheldrick, G. M. (1990). SHELXS97.  Program for the Solution of Crystal 
        Structures.  Univ. of Göttingen, Germany. 

Sheldrick, G. M. (1997). SHELXL97.  Program for the Refinement of 
        Crystal Structures. Univ. of Göttingen, Germany.

Spek, A. L. (1990). Acta Cryst. A36, C--34.


Zsolnai, L., Pritzkow, H. & Hutter, G. (1996). ZORTEP. University
        of Heidelberg, Germany.

;

_publ_section_exptl_refinement
;

All H atoms were placed in calculated positions using a riding
model, except those involved in H-bonds.

;
#=====================================================================

data_4c
 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H23 N O5' 
_chemical_formula_weight          333.37 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    'P 21' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    11.629(2) 
_cell_length_b                    5.8452(12) 
_cell_length_c                    13.118(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  102.60(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      870.2(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       10.41 
_cell_measurement_theta_max       13.93 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.46 
_exptl_crystal_size_mid           0.33 
_exptl_crystal_size_min           0.26 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.272 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              356 
_exptl_absorpt_coefficient_mu     0.093 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 

_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoKα 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius CAD-4 diffractometer' 
_diffrn_measurement_method        ω--2θ 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   60 
_diffrn_standards_decay_%         0.5 
_diffrn_reflns_number             1958 
_diffrn_reflns_av_R_equivalents   0.0358 
_diffrn_reflns_av_sigmaI/netI     0.0343 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        7 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          2.65 
_diffrn_reflns_theta_max          25.97 
_reflns_number_total              1877 
_reflns_number_gt                 1277 
_reflns_threshold_expression      >2sigma(I) 


_computing_data_collection        'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_cell_refinement         
;
SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994)
;
_computing_data_reduction         'MolEN     (Fair, 1990)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     
;
 ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) 
;
_computing_publication_material    
; 
SHELXL-97. All calculations were performed on a DEC 3000 AXP and 
PC/486 computer.

_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
 'calc w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.2745P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    1(3) 
_refine_ls_number_reflns          1877 
_refine_ls_number_parameters      220 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0946 
_refine_ls_R_factor_gt            0.0509 
_refine_ls_wR_factor_ref          0.1561 
_refine_ls_wR_factor_gt           0.1199 
_refine_ls_goodness_of_fit_ref    1.106 
_refine_ls_restrained_S_all       1.106 
_refine_ls_shift/su_max           0.041 
_refine_ls_shift/su_mean          0.002 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O -0.0340(2) 1.0652(7) 0.0319(2) 0.0685(10) Uani 1 d . . . 
O2 O 0.1466(2) 0.9744(7) 0.1182(2) 0.0675(9) Uani 1 d . . . 
O3 O -0.0495(3) 0.5932(8) 0.2902(3) 0.0828(12) Uani 1 d . . . 
O4 O 0.2910(3) 0.6985(7) 0.4723(3) 0.0734(10) Uani 1 d . . . 
O5 O 0.5319(4) 0.8611(10) 0.5467(4) 0.1032(15) Uani 1 d . . . 
H5O H 0.543(6) 0.785(14) 0.487(6) 0.124 Uiso 1 d . . . 
N N -0.0207(2) 0.8556(7) 0.1748(2) 0.0505(9) Uani 1 d . . . 
C1 C -0.1476(3) 0.8973(9) 0.1392(3) 0.0527(11) Uani 1 d . . . 
H1 H -0.1900 0.7515 0.1348 0.079 Uiso 1 calc R . . 
C2 C -0.1533(4) 0.9878(13) 0.0312(3) 0.0742(16) Uani 1 d . . . 
H2A H -0.1772 0.8686 -0.0205 0.111 Uiso 1 calc R . . 
H2B H -0.2088 1.1136 0.0159 0.111 Uiso 1 calc R . . 
C3 C 0.0426(3) 0.9671(9) 0.1104(3) 0.0549(11) Uani 1 d . . . 
C4 C 0.0211(3) 0.7085(9) 0.2576(3) 0.0571(11) Uani 1 d . . . 
C6 C 0.1679(4) 0.6976(10) 0.4246(3) 0.0601(12) Uani 1 d . . . 
H6 H 0.1325 0.5581 0.4456 0.090 Uiso 1 calc R . . 
C5 C 0.1517(3) 0.6982(10) 0.3059(3) 0.0565(11) Uani 1 d . . . 
H5 H 0.1904 0.8335 0.2847 0.085 Uiso 1 calc R . . 
C7 C 0.1150(4) 0.9034(13) 0.4682(4) 0.0849(19) Uani 1 d . . . 
H7A H 0.0550 0.8559 0.5049 0.127 Uiso 1 calc R . . 
H7B H 0.0798 1.0078 0.4126 0.127 Uiso 1 calc R . . 
C8 C 0.2180(5) 1.0165(13) 0.5430(4) 0.0880(18) Uani 1 d . . . 
H8A H 0.2128 1.1819 0.5381 0.132 Uiso 1 calc R . . 
H8B H 0.2210 0.9707 0.6146 0.132 Uiso 1 calc R . . 
C9 C 0.3237(4) 0.9285(10) 0.5056(4) 0.0674(14) Uani 1 d . . . 
H9 H 0.3351 1.0195 0.4458 0.101 Uiso 1 calc R . . 
C10 C 0.4354(4) 0.9246(14) 0.5878(4) 0.0842(19) Uani 1 d . . . 
H10A H 0.4494 1.0752 0.6191 0.126 Uiso 1 calc R . . 
H10B H 0.4270 0.8175 0.6422 0.126 Uiso 1 calc R . . 
C11 C -0.1924(3) 1.0564(10) 0.2132(3) 0.0628(13) Uani 1 d . . . 
H11A H -0.1550 1.2047 0.2130 0.094 Uiso 1 calc R . . 
H11B H -0.1707 0.9954 0.2835 0.094 Uiso 1 calc R . . 
C12 C -0.3253(3) 1.0859(9) 0.1830(3) 0.0530(10) Uani 1 d . . . 
C13 C -0.3773(4) 1.2726(9) 0.1291(4) 0.0677(14) Uani 1 d . . . 
H13 H -0.3301 1.3844 0.1086 0.081 Uiso 1 calc R . . 
C14 C -0.5677(4) 1.1341(12) 0.1327(4) 0.0794(17) Uani 1 d . . . 
H14 H -0.6492 1.1508 0.1163 0.095 Uiso 1 calc R . . 
C15 C -0.4975(5) 1.2989(11) 0.1043(5) 0.0812(16) Uani 1 d . . . 
H15 H -0.5310 1.4283 0.0684 0.097 Uiso 1 calc R . . 
C16 C -0.5179(4) 0.9451(13) 0.1850(4) 0.0819(17) Uani 1 d . . . 
H16 H -0.5654 0.8317 0.2037 0.098 Uiso 1 calc R . . 
C17 C -0.3967(4) 0.9215(10) 0.2104(4) 0.0687(14) Uani 1 d . . . 
H17 H -0.3633 0.7924 0.2466 0.082 Uiso 1 calc R . . 
C18 C 0.2050(5) 0.4831(15) 0.2689(4) 0.104(3) Uani 1 d . . . 
H18A H 0.2880 0.4783 0.2991 0.157 Uiso 1 calc R . . 
H18B H 0.1929 0.4855 0.1941 0.157 Uiso 1 calc R . . 
H18C H 0.1677 0.3502 0.2901 0.157 Uiso 1 calc R . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1 0.0534(17) 0.087(3) 0.0660(18) 0.0212(19) 0.0155(13) 0.0032(18) 
O2 0.0465(16) 0.081(3) 0.0784(19) 0.006(2) 0.0203(13) -0.0141(18) 
O3 0.0588(19) 0.090(3) 0.097(2) 0.032(2) 0.0112(17) -0.018(2) 
O4 0.0614(19) 0.076(2) 0.073(2) -0.013(2) -0.0051(15) 0.009(2) 
O5 0.083(3) 0.104(4) 0.111(3) -0.016(3) -0.003(2) 0.005(3) 
N 0.0356(16) 0.063(2) 0.0524(18) 0.0032(19) 0.0081(13) -0.0049(17) 
C1 0.0345(18) 0.064(3) 0.057(2) 0.003(2) 0.0049(16) -0.0004(19) 
C2 0.049(2) 0.111(5) 0.062(3) 0.004(3) 0.0113(19) 0.005(3) 
C3 0.049(2) 0.058(3) 0.057(2) 0.002(2) 0.0120(18) -0.010(2) 
C4 0.047(2) 0.062(3) 0.061(2) 0.007(3) 0.0095(19) -0.003(2) 
C6 0.052(2) 0.068(3) 0.059(2) -0.001(3) 0.0080(19) -0.003(2) 
C5 0.042(2) 0.066(3) 0.059(2) 0.008(3) 0.0058(17) 0.005(2) 
C7 0.072(3) 0.107(5) 0.078(3) -0.021(4) 0.021(3) 0.014(3) 
C8 0.084(3) 0.096(5) 0.083(3) -0.022(4) 0.017(3) 0.008(3) 
C9 0.072(3) 0.071(4) 0.057(2) -0.005(3) 0.009(2) -0.004(3) 
C10 0.072(3) 0.112(6) 0.064(3) -0.010(4) 0.005(2) -0.008(4) 
C11 0.043(2) 0.076(4) 0.068(3) -0.015(3) 0.0092(18) 0.001(2) 
C12 0.046(2) 0.054(3) 0.060(2) -0.003(2) 0.0132(18) -0.002(2) 
C13 0.057(3) 0.055(3) 0.093(4) 0.006(3) 0.022(2) -0.004(2) 
C14 0.048(3) 0.092(5) 0.097(4) -0.005(4) 0.014(2) 0.009(3) 
C15 0.066(3) 0.073(4) 0.103(4) 0.019(3) 0.017(3) 0.022(3) 
C16 0.052(3) 0.086(4) 0.113(4) 0.013(4) 0.029(3) -0.008(3) 
C17 0.061(3) 0.067(4) 0.082(3) 0.022(3) 0.024(2) 0.000(3) 
C18 0.091(4) 0.136(7) 0.074(3) -0.030(4) -0.010(3) 0.047(4) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C3 1.335(5) . ? 
O1 C2 1.458(5) . ? 
O2 C3 1.191(4) . ? 
O3 C4 1.211(5) . ? 
O4 C6 1.432(5) . ? 
O4 C9 1.439(7) . ? 
O5 C10 1.397(7) . ? 
N C4 1.387(6) . ? 
N C3 1.398(5) . ? 
N C1 1.468(4) . ? 
C1 C2 1.500(6) . ? 
C1 C11 1.516(6) . ? 
C4 C5 1.514(5) . ? 
C6 C7 1.519(8) . ? 
C6 C5 1.526(6) . ? 
C5 C18 1.528(8) . ? 
C7 C8 1.524(8) . ? 
C8 C9 1.511(7) . ? 
C9 C10 1.497(6) . ? 
C11 C12 1.520(5) . ? 
C12 C13 1.367(7) . ? 
C12 C17 1.368(6) . ? 
C13 C15 1.373(7) . ? 
C14 C16 1.362(9) . ? 
C14 C15 1.366(8) . ? 
C16 C17 1.382(6) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C3 O1 C2 110.2(4) . . ? 
C6 O4 C9 108.0(4) . . ? 
C4 N C3 128.4(3) . . ? 
C4 N C1 120.6(3) . . ? 
C3 N C1 110.8(3) . . ? 
N C1 C2 101.2(3) . . ? 
N C1 C11 111.1(3) . . ? 
C2 C1 C11 115.9(5) . . ? 
O1 C2 C1 104.9(3) . . ? 
O2 C3 O1 123.1(4) . . ? 
O2 C3 N 128.5(4) . . ? 
O1 C3 N 108.4(3) . . ? 
O3 C4 N 118.2(4) . . ? 
O3 C4 C5 121.7(4) . . ? 
N C4 C5 120.1(4) . . ? 
O4 C6 C7 106.3(4) . . ? 
O4 C6 C5 109.6(3) . . ? 
C7 C6 C5 114.3(4) . . ? 
C4 C5 C6 108.5(3) . . ? 
C4 C5 C18 109.8(4) . . ? 
C6 C5 C18 110.7(4) . . ? 
C6 C7 C8 105.0(4) . . ? 
C9 C8 C7 103.0(4) . . ? 
O4 C9 C10 109.5(5) . . ? 
O4 C9 C8 103.7(4) . . ? 
C10 C9 C8 114.3(4) . . ? 
O5 C10 C9 111.7(4) . . ? 
C1 C11 C12 112.1(3) . . ? 
C13 C12 C17 118.1(4) . . ? 
C13 C12 C11 122.4(4) . . ? 
C17 C12 C11 119.5(5) . . ? 
C12 C13 C15 121.6(5) . . ? 
C16 C14 C15 119.7(5) . . ? 
C14 C15 C13 119.6(5) . . ? 
C14 C16 C17 120.1(6) . . ? 
C12 C17 C16 120.8(5) . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C4 N C1 C2 -160.2(5) . . . . ? 
C3 N C1 C2 15.4(5) . . . . ? 
C4 N C1 C11 76.1(5) . . . . ? 
C3 N C1 C11 -108.3(4) . . . . ? 
C3 O1 C2 C1 19.8(6) . . . . ? 
N C1 C2 O1 -20.2(6) . . . . ? 
C11 C1 C2 O1 100.1(4) . . . . ? 
C2 O1 C3 O2 168.1(5) . . . . ? 
C2 O1 C3 N -10.1(5) . . . . ? 
C4 N C3 O2 -6.8(8) . . . . ? 
C1 N C3 O2 177.9(5) . . . . ? 
C4 N C3 O1 171.2(5) . . . . ? 
C1 N C3 O1 -4.0(5) . . . . ? 
C3 N C4 O3 -165.2(5) . . . . ? 
C1 N C4 O3 9.6(7) . . . . ? 
C3 N C4 C5 15.9(7) . . . . ? 
C1 N C4 C5 -169.2(4) . . . . ? 
C9 O4 C6 C7 -23.2(5) . . . . ? 
C9 O4 C6 C5 100.9(5) . . . . ? 
O3 C4 C5 C6 -43.4(7) . . . . ? 
N C4 C5 C6 135.4(5) . . . . ? 
O3 C4 C5 C18 77.7(6) . . . . ? 
N C4 C5 C18 -103.4(6) . . . . ? 
O4 C6 C5 C4 -177.4(4) . . . . ? 
C7 C6 C5 C4 -58.1(6) . . . . ? 
O4 C6 C5 C18 62.1(6) . . . . ? 
C7 C6 C5 C18 -178.7(5) . . . . ? 
O4 C6 C7 C8 0.0(6) . . . . ? 
C5 C6 C7 C8 -121.0(5) . . . . ? 
C6 C7 C8 C9 21.4(6) . . . . ? 
C6 O4 C9 C10 159.5(4) . . . . ? 
C6 O4 C9 C8 37.1(5) . . . . ? 
C7 C8 C9 O4 -35.3(6) . . . . ? 
C7 C8 C9 C10 -154.5(6) . . . . ? 
O4 C9 C10 O5 69.4(7) . . . . ? 
C8 C9 C10 O5 -174.8(6) . . . . ? 
N C1 C11 C12 -175.1(4) . . . . ? 
C2 C1 C11 C12 70.1(5) . . . . ? 
C1 C11 C12 C13 -99.7(6) . . . . ? 
C1 C11 C12 C17 80.4(5) . . . . ? 
C17 C12 C13 C15 1.3(7) . . . . ? 
C11 C12 C13 C15 -178.6(5) . . . . ? 
C16 C14 C15 C13 -0.1(9) . . . . ? 
C12 C13 C15 C14 -0.9(8) . . . . ? 
C15 C14 C16 C17 0.8(9) . . . . ? 
C13 C12 C17 C16 -0.6(7) . . . . ? 
C11 C12 C17 C16 179.3(5) . . . . ? 
C14 C16 C17 C12 -0.4(8) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              25.97 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.284 
_refine_diff_density_min   -0.240 
_refine_diff_density_rms    0.049 

#======END
 
data_6c 
 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H23 N O5' 
_chemical_formula_weight          333.37 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    'P 21 21 21' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 
_cell_length_a                    8.469(2) 
_cell_length_b                    12.459(3) 
_cell_length_c                    16.239(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1713.5(7) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       10.14 
_cell_measurement_theta_max       13.92 
 
_exptl_crystal_description        irregular 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.58 
_exptl_crystal_size_mid           0.36 
_exptl_crystal_size_min           0.33 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.292 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              712 
_exptl_absorpt_coefficient_mu     0.094 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
_diffrn_measurement_device_type   'Nonius CAD-4 diffractometer' 
_diffrn_measurement_method        ω--2θ 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   60 
_diffrn_standards_decay_%         0.4 
_diffrn_reflns_number             1935 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0296 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        0 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        0 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        0 
_diffrn_reflns_theta_min          2.51 
_diffrn_reflns_theta_max          25.96 
_reflns_number_total              1935 
_reflns_number_gt                 1432 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_cell_refinement         
;
SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994)
;
_computing_data_reduction         'MolEN     (Fair, 1990)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     
;
 ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) 
;
_computing_publication_material    
; 
SHELXL-97. All calculations were performed on a DEC 3000 AXP and 
PC/486 computer.

_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
 'calc w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.5860P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.023(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    2(3) 
_refine_ls_number_reflns          1935 
_refine_ls_number_parameters      221 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0762 
_refine_ls_R_factor_gt            0.0441 
_refine_ls_wR_factor_ref          0.1365 
_refine_ls_wR_factor_gt           0.1112 
_refine_ls_goodness_of_fit_ref    1.097 
_refine_ls_restrained_S_all       1.097 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.8853(4) 0.4525(2) 0.93337(19) 0.0732(9) Uani 1 d . . . 
O2 O 0.7786(5) 0.5075(2) 0.81592(18) 0.0872(11) Uani 1 d . . . 
O3 O 0.7057(4) 0.7844(2) 0.95953(15) 0.0606(7) Uani 1 d . . . 
O4 O 0.4298(3) 0.7294(3) 0.83570(15) 0.0609(8) Uani 1 d . . . 
O5 O 0.1391(4) 0.6224(3) 0.8778(2) 0.0810(10) Uani 1 d . . . 
H5O H 0.216(6) 0.674(4) 0.924(3) 0.097 Uiso 1 d . . . 
N N 0.7788(4) 0.6149(2) 0.93334(16) 0.0445(7) Uani 1 d . . . 
C1 C 0.8223(4) 0.5976(3) 1.0203(2) 0.0474(9) Uani 1 d . . . 
H1 H 0.8863 0.6582 1.0394 0.071 Uiso 1 calc R . . 
C2 C 0.9271(5) 0.4987(3) 1.0119(3) 0.0658(11) Uani 1 d . . . 
H2A H 1.0378 0.5186 1.0129 0.099 Uiso 1 calc R . . 
H2B H 0.9069 0.4483 1.0562 0.099 Uiso 1 calc R . . 
C3 C 0.8111(6) 0.5247(3) 0.8863(3) 0.0613(11) Uani 1 d . . . 
C4 C 0.7284(4) 0.7155(3) 0.9074(2) 0.0451(8) Uani 1 d . . . 
C5 C 0.7130(4) 0.7380(3) 0.8165(2) 0.0510(9) Uani 1 d . . . 
H5 H 0.7233 0.6709 0.7855 0.076 Uiso 1 calc R . . 
C6 C 0.5539(4) 0.7896(4) 0.7975(2) 0.0531(10) Uani 1 d . . . 
H6 H 0.5526 0.8637 0.8178 0.080 Uiso 1 calc R . . 
C7 C 0.5178(6) 0.7878(5) 0.7053(3) 0.0822(16) Uani 1 d . . . 
H7A H 0.4674 0.8540 0.6879 0.123 Uiso 1 calc R . . 
H7B H 0.6131 0.7770 0.6732 0.123 Uiso 1 calc R . . 
C8 C 0.4057(6) 0.6926(6) 0.6969(3) 0.101(2) Uani 1 d . . . 
H8A H 0.3376 0.7000 0.6492 0.152 Uiso 1 calc R . . 
H8B H 0.4629 0.6253 0.6933 0.152 Uiso 1 calc R . . 
C9 C 0.3143(5) 0.7007(4) 0.7756(2) 0.0612(11) Uani 1 d . . . 
H9 H 0.2382 0.7596 0.7706 0.092 Uiso 1 calc R . . 
C10 C 0.2304(6) 0.6042(4) 0.8046(3) 0.0826(14) Uani 1 d . . . 
H10A H 0.1608 0.5791 0.7612 0.124 Uiso 1 calc R . . 
H10B H 0.3070 0.5480 0.8154 0.124 Uiso 1 calc R . . 
C11 C 0.6808(5) 0.5837(3) 1.0775(2) 0.0537(9) Uani 1 d . . . 
H11A H 0.7195 0.5758 1.1334 0.080 Uiso 1 calc R . . 
H11B H 0.6180 0.6488 1.0756 0.080 Uiso 1 calc R . . 
C12 C 0.5748(4) 0.4896(3) 1.0581(2) 0.0471(8) Uani 1 d . . . 
C13 C 0.4577(5) 0.4985(3) 0.9985(2) 0.0549(10) Uani 1 d . . . 
H13 H 0.4443 0.5630 0.9704 0.066 Uiso 1 calc R . . 
C14 C 0.3610(5) 0.4121(3) 0.9805(3) 0.0600(11) Uani 1 d . . . 
H14 H 0.2830 0.4191 0.9406 0.072 Uiso 1 calc R . . 
C15 C 0.3791(5) 0.3160(3) 1.0211(3) 0.0627(11) Uani 1 d . . . 
H15 H 0.3154 0.2575 1.0082 0.075 Uiso 1 calc R . . 
C16 C 0.4929(6) 0.3079(3) 1.0808(3) 0.0669(12) Uani 1 d . . . 
H16 H 0.5051 0.2435 1.1091 0.080 Uiso 1 calc R . . 
C17 C 0.5885(5) 0.3926(3) 1.0995(2) 0.0603(11) Uani 1 d . . . 
H17 H 0.6640 0.3852 1.1407 0.072 Uiso 1 calc R . . 
C18 C 0.8479(5) 0.8142(5) 0.7932(3) 0.0859(17) Uani 1 d . . . 
H18A H 0.8419 0.8306 0.7355 0.129 Uiso 1 calc R . . 
H18B H 0.9473 0.7804 0.8049 0.129 Uiso 1 calc R . . 
H18C H 0.8391 0.8792 0.8246 0.129 Uiso 1 calc R . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1 0.094(2) 0.0435(15) 0.082(2) 0.0032(15) 0.0059(19) 0.0135(17) 
O2 0.138(3) 0.0609(18) 0.0626(18) -0.0147(15) -0.003(2) 0.005(2) 
O3 0.0804(18) 0.0487(14) 0.0525(14) -0.0049(12) -0.0002(15) 0.0120(16) 
O4 0.0481(14) 0.091(2) 0.0440(13) 0.0043(14) -0.0018(12) -0.0089(16) 
O5 0.0697(19) 0.090(2) 0.083(2) -0.0046(19) 0.0015(18) -0.015(2) 
N 0.0476(15) 0.0417(15) 0.0444(15) -0.0010(12) -0.0022(14) 0.0022(14) 
C1 0.049(2) 0.0426(18) 0.0503(19) 0.0055(15) -0.0033(17) -0.0032(17) 
C2 0.063(2) 0.061(2) 0.074(3) 0.014(2) -0.002(2) 0.006(2) 
C3 0.079(3) 0.044(2) 0.062(2) -0.0028(18) 0.005(2) 0.000(2) 
C4 0.0410(17) 0.0435(18) 0.0508(19) 0.0016(16) -0.0015(16) 0.0013(17) 
C5 0.049(2) 0.057(2) 0.0477(19) 0.0047(17) 0.0023(18) 0.0085(19) 
C6 0.0446(19) 0.065(2) 0.050(2) 0.0084(19) 0.0051(17) 0.004(2) 
C7 0.057(3) 0.134(4) 0.056(2) 0.032(3) 0.000(2) 0.015(3) 
C8 0.076(3) 0.178(6) 0.050(2) -0.015(3) -0.007(2) 0.002(4) 
C9 0.048(2) 0.083(3) 0.053(2) -0.009(2) -0.0041(19) 0.003(2) 
C10 0.073(3) 0.091(3) 0.084(3) -0.018(3) -0.013(3) -0.003(3) 
C11 0.067(2) 0.048(2) 0.0461(18) -0.0013(16) -0.0015(19) -0.005(2) 
C12 0.050(2) 0.0475(19) 0.0436(17) 0.0003(16) 0.0028(17) 0.0018(18) 
C13 0.058(2) 0.054(2) 0.054(2) 0.004(2) 0.0052(19) 0.005(2) 
C14 0.050(2) 0.072(3) 0.058(2) -0.007(2) -0.0005(19) 0.001(2) 
C15 0.061(2) 0.062(3) 0.064(2) -0.006(2) 0.013(2) -0.011(2) 
C16 0.077(3) 0.049(2) 0.075(3) 0.013(2) 0.002(2) -0.010(2) 
C17 0.061(2) 0.063(2) 0.058(2) 0.0166(19) -0.004(2) 0.000(2) 
C18 0.046(2) 0.139(5) 0.073(3) 0.026(3) 0.004(2) -0.008(3) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C3 1.337(5) . ? 
O1 C2 1.443(5) . ? 
O2 C3 1.195(5) . ? 
O3 C4 1.220(4) . ? 
O4 C9 1.427(5) . ? 
O4 C6 1.432(5) . ? 
O5 C10 1.437(6) . ? 
N C3 1.386(5) . ? 
N C4 1.388(4) . ? 
N C1 1.475(4) . ? 
C1 C2 1.525(5) . ? 
C1 C11 1.526(5) . ? 
C4 C5 1.510(5) . ? 
C5 C6 1.523(5) . ? 
C5 C18 1.532(6) . ? 
C6 C7 1.530(5) . ? 
C7 C8 1.525(8) . ? 
C8 C9 1.498(6) . ? 
C9 C10 1.473(7) . ? 
C11 C12 1.511(5) . ? 
C12 C17 1.388(5) . ? 
C12 C13 1.391(5) . ? 
C13 C14 1.383(6) . ? 
C14 C15 1.375(6) . ? 
C15 C16 1.371(6) . ? 
C16 C17 1.364(6) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C3 O1 C2 110.6(3) . . ? 
C9 O4 C6 109.8(3) . . ? 
C3 N C4 128.7(3) . . ? 
C3 N C1 111.1(3) . . ? 
C4 N C1 119.9(3) . . ? 
N C1 C2 100.3(3) . . ? 
N C1 C11 113.8(3) . . ? 
C2 C1 C11 114.8(3) . . ? 
O1 C2 C1 105.0(3) . . ? 
O2 C3 O1 122.3(4) . . ? 
O2 C3 N 128.8(4) . . ? 
O1 C3 N 108.9(3) . . ? 
O3 C4 N 118.2(3) . . ? 
O3 C4 C5 122.3(3) . . ? 
N C4 C5 119.4(3) . . ? 
C4 C5 C6 110.6(3) . . ? 
C4 C5 C18 107.0(3) . . ? 
C6 C5 C18 110.4(3) . . ? 
O4 C6 C5 110.0(3) . . ? 
O4 C6 C7 105.6(3) . . ? 
C5 C6 C7 111.6(3) . . ? 
C8 C7 C6 102.9(4) . . ? 
C9 C8 C7 101.1(4) . . ? 
O4 C9 C10 108.4(4) . . ? 
O4 C9 C8 104.3(3) . . ? 
C10 C9 C8 117.8(4) . . ? 
O5 C10 C9 113.3(4) . . ? 
C12 C11 C1 115.3(3) . . ? 
C17 C12 C13 117.8(4) . . ? 
C17 C12 C11 121.7(3) . . ? 
C13 C12 C11 120.4(3) . . ? 
C14 C13 C12 120.4(4) . . ? 
C15 C14 C13 120.7(4) . . ? 
C16 C15 C14 118.7(4) . . ? 
C17 C16 C15 121.2(4) . . ? 
C16 C17 C12 121.1(4) . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C3 N C1 C2 15.8(4) . . . . ? 
C4 N C1 C2 -158.2(3) . . . . ? 
C3 N C1 C11 -107.3(4) . . . . ? 
C4 N C1 C11 78.7(4) . . . . ? 
C3 O1 C2 C1 18.6(4) . . . . ? 
N C1 C2 O1 -19.7(4) . . . . ? 
C11 C1 C2 O1 102.6(4) . . . . ? 
C2 O1 C3 O2 172.9(5) . . . . ? 
C2 O1 C3 N -8.7(5) . . . . ? 
C4 N C3 O2 -13.8(8) . . . . ? 
C1 N C3 O2 172.9(5) . . . . ? 
C4 N C3 O1 167.9(3) . . . . ? 
C1 N C3 O1 -5.4(5) . . . . ? 
C3 N C4 O3 179.6(4) . . . . ? 
C1 N C4 O3 -7.6(5) . . . . ? 
C3 N C4 C5 -4.0(6) . . . . ? 
C1 N C4 C5 168.8(3) . . . . ? 
O3 C4 C5 C6 -52.3(5) . . . . ? 
N C4 C5 C6 131.4(4) . . . . ? 
O3 C4 C5 C18 68.0(5) . . . . ? 
N C4 C5 C18 -108.2(4) . . . . ? 
C9 O4 C6 C5 -126.2(4) . . . . ? 
C9 O4 C6 C7 -5.6(5) . . . . ? 
C4 C5 C6 O4 -49.0(4) . . . . ? 
C18 C5 C6 O4 -167.2(4) . . . . ? 
C4 C5 C6 C7 -165.9(4) . . . . ? 
C18 C5 C6 C7 75.9(5) . . . . ? 
O4 C6 C7 C8 -19.4(5) . . . . ? 
C5 C6 C7 C8 100.1(4) . . . . ? 
C6 C7 C8 C9 35.7(5) . . . . ? 
C6 O4 C9 C10 155.5(4) . . . . ? 
C6 O4 C9 C8 29.1(5) . . . . ? 
C7 C8 C9 O4 -39.9(5) . . . . ? 
C7 C8 C9 C10 -160.1(4) . . . . ? 
O4 C9 C10 O5 65.5(5) . . . . ? 
C8 C9 C10 O5 -176.5(4) . . . . ? 
N C1 C11 C12 60.5(4) . . . . ? 
C2 C1 C11 C12 -54.2(4) . . . . ? 
C1 C11 C12 C17 97.7(4) . . . . ? 
C1 C11 C12 C13 -83.3(4) . . . . ? 
C17 C12 C13 C14 -1.3(5) . . . . ? 
C11 C12 C13 C14 179.7(3) . . . . ? 
C12 C13 C14 C15 -0.2(6) . . . . ? 
C13 C14 C15 C16 1.3(6) . . . . ? 
C14 C15 C16 C17 -0.9(7) . . . . ? 
C15 C16 C17 C12 -0.6(7) . . . . ? 
C13 C12 C17 C16 1.7(6) . . . . ? 
C11 C12 C17 C16 -179.4(4) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              25.96 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.235 
_refine_diff_density_min   -0.159 
_refine_diff_density_rms    0.039 

#======END
 
data_5b 
 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H23 N O5' 
_chemical_formula_weight          333.37 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    'P 21 21 21' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 
_cell_length_a                    8.465(2) 
_cell_length_b                    12.419(3) 
_cell_length_c                    15.796(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1660.6(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       10.45 
_cell_measurement_theta_max       13.21 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.53 
_exptl_crystal_size_mid           0.33 
_exptl_crystal_size_min           0.33 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.333 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              712 
_exptl_absorpt_coefficient_mu     0.097 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 

_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius CAD-4 diffractometer' 
_diffrn_measurement_method        \w--2\q 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   60 
_diffrn_standards_decay_%         0.2 
_diffrn_reflns_number             1687 
_diffrn_reflns_av_R_equivalents   0.0046 
_diffrn_reflns_av_sigmaI/netI     0.0429 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        0 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.73 
_diffrn_reflns_theta_max          24.99 
_reflns_number_total              1686 
_reflns_number_gt                 1200 
_reflns_threshold_expression      >2sigma(I) 


_computing_data_collection        'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_cell_refinement         
;
SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994)
;
_computing_data_reduction         'MolEN     (Fair, 1990)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     
;
 ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) 
;
_computing_publication_material    
; 
SHELXL-97. All calculations were performed on a DEC 3000 AXP and 
PC/486 computer.

_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
 'calc w=1/[\s^2^(Fo^2^)+(0.1007P)^2^+1.4755P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.024(6) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    2(4) 
_refine_ls_number_reflns          1686 
_refine_ls_number_parameters      221 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1078 
_refine_ls_R_factor_gt            0.0614 
_refine_ls_wR_factor_ref          0.2083 
_refine_ls_wR_factor_gt           0.1538 
_refine_ls_goodness_of_fit_ref    1.163 
_refine_ls_restrained_S_all       1.163 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.6366(6) 0.5457(3) 0.5723(3) 0.0530(14) Uani 1 d . . . 
O2 O 0.7490(8) 0.4885(4) 0.6911(3) 0.0656(16) Uani 1 d . . . 
O3 O 0.8061(6) 0.2117(3) 0.5406(3) 0.0502(13) Uani 1 d . . . 
O4 O 1.0823(5) 0.3039(4) 0.6548(3) 0.0459(12) Uani 1 d . . . 
O5 O 1.3931(7) 0.3721(5) 0.6229(3) 0.0658(17) Uani 1 d . . . 
H5O H 1.340(12) 0.336(7) 0.596(6) 0.079 Uiso 1 d . . . 
N N 0.7429(6) 0.3826(4) 0.5686(3) 0.0340(12) Uani 1 d . . . 
C1 C 0.6980(8) 0.4022(5) 0.4806(4) 0.0398(15) Uani 1 d . . . 
H1 H 0.6334 0.3419 0.4605 0.060 Uiso 1 calc R . . 
C2 C 0.5928(9) 0.5005(5) 0.4917(5) 0.0514(19) Uani 1 d . . . 
H2A H 0.6107 0.5520 0.4465 0.077 Uiso 1 calc R . . 
H2B H 0.4823 0.4800 0.4915 0.077 Uiso 1 calc R . . 
C3 C 0.7119(9) 0.4719(5) 0.6186(4) 0.0439(16) Uani 1 d . . . 
C4 C 0.7887(7) 0.2810(4) 0.5936(4) 0.0351(14) Uani 1 d . . . 
C5 C 0.8100(8) 0.2557(5) 0.6870(4) 0.0386(15) Uani 1 d . . . 
H5 H 0.7801 0.3188 0.7207 0.058 Uiso 1 calc R . . 
C6 C 0.9869(8) 0.2305(6) 0.7016(4) 0.0442(17) Uani 1 d . . . 
H6 H 1.0096 0.1567 0.6834 0.066 Uiso 1 calc R . . 
C7 C 1.0376(10) 0.2450(7) 0.7938(4) 0.061(2) Uani 1 d . . . 
H7A H 0.9504 0.2312 0.8321 0.092 Uiso 1 calc R . . 
H7B H 1.1247 0.1975 0.8079 0.092 Uiso 1 calc R . . 
C8 C 1.0880(10) 0.3621(6) 0.7973(5) 0.062(2) Uani 1 d . . . 
H8A H 1.1667 0.3737 0.8410 0.093 Uiso 1 calc R . . 
H8B H 0.9984 0.4089 0.8076 0.093 Uiso 1 calc R . . 
C9 C 1.1573(8) 0.3810(6) 0.7091(4) 0.0459(16) Uani 1 d . . . 
H9 H 1.1324 0.4542 0.6900 0.069 Uiso 1 calc R . . 
C10 C 1.3318(9) 0.3633(6) 0.7063(4) 0.056(2) Uani 1 d . . . 
H10A H 1.3834 0.4158 0.7423 0.084 Uiso 1 calc R . . 
H10B H 1.3556 0.2922 0.7284 0.084 Uiso 1 calc R . . 
C11 C 0.8367(9) 0.4183(5) 0.4198(4) 0.0451(17) Uani 1 d . . . 
H11A H 0.9012 0.3538 0.4201 0.068 Uiso 1 calc R . . 
H11B H 0.7954 0.4272 0.3629 0.068 Uiso 1 calc R . . 
C12 C 0.9408(8) 0.5142(5) 0.4405(4) 0.0374(15) Uani 1 d . . . 
C13 C 0.9166(8) 0.6123(5) 0.4000(4) 0.0424(15) Uani 1 d . . . 
H13 H 0.8366 0.6193 0.3600 0.051 Uiso 1 calc R . . 
C14 C 1.0118(9) 0.6994(5) 0.4193(5) 0.0501(18) Uani 1 d . . . 
H14 H 0.9948 0.7650 0.3923 0.060 Uiso 1 calc R . . 
C15 C 1.1307(9) 0.6905(5) 0.4776(4) 0.0533(19) Uani 1 d . . . 
H15 H 1.1935 0.7497 0.4905 0.064 Uiso 1 calc R . . 
C16 C 1.1568(9) 0.5927(5) 0.5173(4) 0.0485(17) Uani 1 d . . . 
H16 H 1.2384 0.5857 0.5563 0.058 Uiso 1 calc R . . 
C17 C 1.0620(8) 0.5059(5) 0.4991(4) 0.0436(16) Uani 1 d . . . 
H17 H 1.0794 0.4407 0.5264 0.052 Uiso 1 calc R . . 
C18 C 0.7069(10) 0.1610(6) 0.7121(5) 0.062(2) Uani 1 d . . . 
H18A H 0.7213 0.1458 0.7712 0.094 Uiso 1 calc R . . 
H18B H 0.7361 0.0990 0.6794 0.094 Uiso 1 calc R . . 
H18C H 0.5981 0.1783 0.7016 0.094 Uiso 1 calc R . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1 0.074(4) 0.031(2) 0.054(3) 0.006(2) -0.003(3) 0.012(2) 
O2 0.109(5) 0.040(3) 0.047(3) -0.008(2) -0.011(3) 0.003(3) 
O3 0.075(3) 0.033(2) 0.042(2) -0.004(2) 0.002(2) 0.006(3) 
O4 0.050(3) 0.051(3) 0.037(2) 0.000(2) 0.002(2) -0.009(2) 
O5 0.065(4) 0.087(4) 0.046(3) -0.009(3) 0.001(3) -0.027(3) 
N 0.042(3) 0.030(2) 0.031(3) 0.000(2) -0.002(2) 0.003(2) 
C1 0.045(4) 0.038(3) 0.037(3) 0.004(3) -0.007(3) -0.004(3) 
C2 0.052(4) 0.049(4) 0.054(4) 0.012(3) -0.004(4) 0.001(4) 
C3 0.054(4) 0.031(3) 0.047(4) 0.002(3) 0.000(3) -0.001(3) 
C4 0.043(3) 0.029(3) 0.034(3) 0.004(3) 0.004(3) 0.001(3) 
C5 0.043(3) 0.033(3) 0.040(3) 0.008(3) 0.004(3) 0.008(3) 
C6 0.056(4) 0.044(4) 0.033(3) 0.006(3) 0.006(3) 0.004(3) 
C7 0.060(5) 0.081(5) 0.042(4) 0.018(4) 0.001(4) 0.003(4) 
C8 0.063(5) 0.080(5) 0.043(4) -0.009(4) 0.001(4) 0.005(5) 
C9 0.049(4) 0.052(4) 0.037(4) -0.004(3) -0.009(3) 0.004(4) 
C10 0.055(4) 0.065(5) 0.048(4) -0.005(4) 0.000(4) -0.004(4) 
C11 0.062(4) 0.036(3) 0.037(3) -0.001(3) 0.000(3) -0.002(3) 
C12 0.044(4) 0.037(3) 0.031(3) 0.000(3) 0.003(3) 0.002(3) 
C13 0.044(3) 0.046(4) 0.037(3) 0.011(3) -0.001(3) -0.002(3) 
C14 0.057(4) 0.042(4) 0.052(4) 0.007(3) 0.010(4) 0.002(4) 
C15 0.064(5) 0.042(4) 0.054(4) -0.010(3) 0.011(4) -0.012(4) 
C16 0.049(4) 0.057(4) 0.039(4) -0.006(3) -0.005(3) -0.001(4) 
C17 0.052(4) 0.038(4) 0.040(3) 0.002(3) 0.006(3) 0.003(3) 
C18 0.060(5) 0.067(5) 0.060(5) 0.025(4) 0.004(4) -0.008(4) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C3 1.334(8) . ? 
O1 C2 1.440(8) . ? 
O2 C3 1.205(8) . ? 
O3 C4 1.209(7) . ? 
O4 C6 1.425(8) . ? 
O4 C9 1.433(8) . ? 
O5 C10 1.420(9) . ? 
N C4 1.378(7) . ? 
N C3 1.387(8) . ? 
N C1 1.462(7) . ? 
C1 C2 1.521(9) . ? 
C1 C11 1.530(10) . ? 
C4 C5 1.519(8) . ? 
C5 C18 1.517(9) . ? 
C5 C6 1.547(10) . ? 
C6 C7 1.528(9) . ? 
C7 C8 1.517(11) . ? 
C8 C9 1.530(10) . ? 
C9 C10 1.494(10) . ? 
C11 C12 1.518(9) . ? 
C12 C17 1.384(9) . ? 
C12 C13 1.391(8) . ? 
C13 C14 1.383(9) . ? 
C14 C15 1.369(10) . ? 
C15 C16 1.384(9) . ? 
C16 C17 1.374(9) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C3 O1 C2 109.9(5) . . ? 
C6 O4 C9 111.6(5) . . ? 
C4 N C3 128.5(5) . . ? 
C4 N C1 119.9(5) . . ? 
C3 N C1 111.0(5) . . ? 
N C1 C2 100.2(5) . . ? 
N C1 C11 114.8(6) . . ? 
C2 C1 C11 114.6(5) . . ? 
O1 C2 C1 105.3(5) . . ? 
O2 C3 O1 121.9(6) . . ? 
O2 C3 N 128.9(6) . . ? 
O1 C3 N 109.1(5) . . ? 
O3 C4 N 119.1(5) . . ? 
O3 C4 C5 120.7(5) . . ? 
N C4 C5 120.1(5) . . ? 
C18 C5 C4 110.3(6) . . ? 
C18 C5 C6 111.2(5) . . ? 
C4 C5 C6 107.5(5) . . ? 
O4 C6 C7 105.1(6) . . ? 
O4 C6 C5 110.0(5) . . ? 
C7 C6 C5 113.0(6) . . ? 
C8 C7 C6 103.1(6) . . ? 
C7 C8 C9 102.8(6) . . ? 
O4 C9 C10 108.8(6) . . ? 
O4 C9 C8 105.8(6) . . ? 
C10 C9 C8 112.6(6) . . ? 
O5 C10 C9 112.2(6) . . ? 
C12 C11 C1 114.4(5) . . ? 
C17 C12 C13 118.8(6) . . ? 
C17 C12 C11 121.1(6) . . ? 
C13 C12 C11 120.1(6) . . ? 
C14 C13 C12 119.8(6) . . ? 
C15 C14 C13 120.9(6) . . ? 
C14 C15 C16 119.5(7) . . ? 
C17 C16 C15 120.0(7) . . ? 
C16 C17 C12 121.0(6) . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              24.99 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.340 
_refine_diff_density_min   -0.401 
_refine_diff_density_rms    0.082 
 
#======END
 
data_5e 
 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C17 H20 Br N O5' 
_chemical_formula_weight          398.25 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Br'  'Br'  -0.2901   2.4595 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    'P 21 21 21' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 
_cell_length_a                    8.4983(17) 
_cell_length_b                    12.520(3) 
_cell_length_c                    15.821(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1683.4(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       10.38 
_cell_measurement_theta_max       18.29 
 
_exptl_crystal_description        irregular 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.36 
_exptl_crystal_size_mid           0.36 
_exptl_crystal_size_min           0.30 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.571 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              816 
_exptl_absorpt_coefficient_mu     2.469 
_exptl_absorpt_correction_type    psi-scan 
_exptl_absorpt_correction_T_min   0.9981 
_exptl_absorpt_correction_T_max   0.8564 
 
_exptl_special_details 
; 
 ? 
; 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius CAD-4 diffractometer' 
_diffrn_measurement_method        ω--2θ 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   60 
_diffrn_standards_decay_%         0.7 
_diffrn_reflns_number             1961 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0676 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.57 
_diffrn_reflns_theta_max          26.27 
_reflns_number_total              1961 
_reflns_number_gt                 1300 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_cell_refinement         
;
SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994)
;
_computing_data_reduction         'MolEN     (Fair, 1990)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     
;
 ZORTEP (Zsolnai, Pritzkow & Hutter, 1996) 
;
_computing_publication_material    
; 
SHELXL-97. All calculations were performed on a DEC 3000 AXP and 
PC/486 computer.

_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+2.0448P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0124(6) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.02(2) 
_refine_ls_number_reflns          1961 
_refine_ls_number_parameters      221 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1076 
_refine_ls_R_factor_gt            0.0382 
_refine_ls_wR_factor_ref          0.0838 
_refine_ls_wR_factor_gt           0.0569 
_refine_ls_goodness_of_fit_ref    1.205 
_refine_ls_restrained_S_all       1.205 
_refine_ls_shift/su_max           0.014 
_refine_ls_shift/su_mean          0.001 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Br1 Br 0.17995(10) 0.65136(6) 0.72459(5) 0.0576(3) Uani 1 d . . . 
O1 O 0.8981(6) 0.8709(5) 0.6226(3) 0.0579(17) Uani 1 d . . . 
H1O H 0.848(10) 0.850(7) 0.589(5) 0.069 Uiso 1 d . . . 
O2 O 0.5875(6) 0.8026(4) 0.6546(3) 0.0436(13) Uani 1 d . . . 
O3 O 0.3118(7) 0.7146(3) 0.5422(3) 0.0444(12) Uani 1 d . . . 
O4 O 0.2429(7) 0.9882(4) 0.6910(3) 0.0580(16) Uani 1 d . . . 
O5 O 0.1352(6) 1.0458(4) 0.5713(3) 0.0493(14) Uani 1 d . . . 
N N 0.2446(6) 0.8846(4) 0.5689(3) 0.0292(13) Uani 1 d . . . 
C1 C 0.6648(8) 0.8780(5) 0.7108(4) 0.0430(17) Uani 1 d . . . 
H1 H 0.6410 0.9512 0.6928 0.052 Uiso 1 calc R . . 
C2 C 0.5959(9) 0.8582(7) 0.7972(4) 0.058(2) Uani 1 d . . . 
H2A H 0.5074 0.9052 0.8078 0.070 Uiso 1 calc R . . 
H2B H 0.6743 0.8689 0.8410 0.070 Uiso 1 calc R . . 
C3 C 0.5436(9) 0.7426(7) 0.7939(4) 0.055(2) Uani 1 d . . . 
H3A H 0.4570 0.7294 0.8324 0.066 Uiso 1 calc R . . 
H3B H 0.6296 0.6946 0.8073 0.066 Uiso 1 calc R . . 
C4 C 0.4920(8) 0.7306(5) 0.7020(4) 0.0385(18) Uani 1 d . . . 
H4 H 0.5085 0.6571 0.6827 0.046 Uiso 1 calc R . . 
C5 C 0.3199(8) 0.7643(5) 0.6877(4) 0.0335(15) Uani 1 d . . . 
H5 H 0.2977 0.8296 0.7197 0.040 Uiso 1 calc R . . 
C6 C 0.2920(8) 0.7841(5) 0.5949(4) 0.0343(17) Uani 1 d . . . 
C7 C 0.2108(9) 0.9733(6) 0.6189(5) 0.045(2) Uani 1 d . . . 
C8 C 0.0936(9) 1.0007(6) 0.4906(5) 0.049(2) Uani 1 d . . . 
H8A H 0.1129 1.0516 0.4455 0.059 Uiso 1 calc R . . 
H8B H -0.0166 0.9806 0.4896 0.059 Uiso 1 calc R . . 
C9 C 0.1979(8) 0.9031(5) 0.4806(4) 0.0339(16) Uani 1 d . . . 
H9 H 0.1348 0.8427 0.4605 0.041 Uiso 1 calc R . . 
C10 C 0.3389(9) 0.9198(5) 0.4218(4) 0.0393(17) Uani 1 d . . . 
H10A H 0.4033 0.8558 0.4232 0.047 Uiso 1 calc R . . 
H10B H 0.3001 0.9280 0.3645 0.047 Uiso 1 calc R . . 
C11 C 0.4405(8) 1.0132(5) 0.4422(4) 0.0316(16) Uani 1 d . . . 
C12 C 0.5614(8) 1.0051(6) 0.5012(5) 0.0404(18) Uani 1 d . . . 
H12 H 0.5788 0.9400 0.5278 0.049 Uiso 1 calc R . . 
C13 C 0.6559(10) 1.0909(6) 0.5213(4) 0.046(2) Uani 1 d . . . 
H13 H 0.7368 1.0828 0.5604 0.055 Uiso 1 calc R . . 
C14 C 0.6311(9) 1.1882(6) 0.4837(5) 0.049(2) Uani 1 d . . . 
H14 H 0.6919 1.2471 0.4984 0.058 Uiso 1 calc R . . 
C15 C 0.5147(9) 1.1970(5) 0.4239(5) 0.048(2) Uani 1 d . . . 
H15 H 0.5001 1.2620 0.3966 0.058 Uiso 1 calc R . . 
C16 C 0.4191(9) 1.1121(5) 0.4034(4) 0.0424(19) Uani 1 d . . . 
H16 H 0.3398 1.1207 0.3635 0.051 Uiso 1 calc R . . 
C17 C 0.8386(8) 0.8590(6) 0.7054(4) 0.0478(18) Uani 1 d . . . 
H17A H 0.8921 0.9089 0.7425 0.057 Uiso 1 calc R . . 
H17B H 0.8614 0.7874 0.7252 0.057 Uiso 1 calc R . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
Br1 0.0491(4) 0.0617(5) 0.0619(5) 0.0236(5) 0.0040(5) -0.0074(5) 
O1 0.045(3) 0.082(5) 0.047(4) 0.000(3) 0.004(3) -0.015(3) 
O2 0.046(3) 0.054(3) 0.030(3) -0.002(2) 0.003(2) -0.010(3) 
O3 0.060(3) 0.037(3) 0.037(2) -0.007(2) -0.001(3) 0.005(3) 
O4 0.099(4) 0.035(3) 0.040(3) -0.007(2) -0.003(3) 0.014(3) 
O5 0.061(4) 0.037(3) 0.050(3) 0.006(3) -0.002(3) 0.012(3) 
N 0.030(3) 0.028(3) 0.030(3) 0.003(2) -0.004(2) 0.005(2) 
C1 0.044(4) 0.046(4) 0.039(4) -0.011(3) -0.005(4) 0.000(4) 
C2 0.046(4) 0.099(7) 0.029(4) -0.016(5) -0.004(3) 0.008(5) 
C3 0.047(5) 0.088(6) 0.031(5) 0.021(4) 0.003(4) 0.003(5) 
C4 0.042(4) 0.035(4) 0.039(4) 0.011(3) 0.009(3) 0.008(3) 
C5 0.040(4) 0.032(3) 0.028(3) 0.004(3) 0.002(4) 0.005(4) 
C6 0.035(4) 0.034(4) 0.035(4) 0.002(3) 0.002(3) -0.012(3) 
C7 0.053(5) 0.038(4) 0.043(4) 0.003(4) 0.005(4) 0.002(4) 
C8 0.051(5) 0.050(5) 0.047(5) 0.012(4) -0.004(5) 0.002(4) 
C9 0.034(4) 0.033(4) 0.035(4) 0.006(3) -0.002(4) -0.002(3) 
C10 0.055(5) 0.030(3) 0.032(4) 0.004(3) 0.003(4) 0.008(4) 
C11 0.035(4) 0.032(4) 0.028(4) -0.002(3) 0.001(3) -0.001(3) 
C12 0.048(4) 0.035(4) 0.038(4) 0.005(4) 0.003(4) 0.005(4) 
C13 0.044(5) 0.055(5) 0.038(4) -0.001(4) -0.005(4) 0.001(5) 
C14 0.048(5) 0.048(5) 0.050(5) -0.010(4) 0.008(4) -0.011(4) 
C15 0.052(5) 0.030(4) 0.062(5) 0.009(4) 0.010(5) 0.010(4) 
C16 0.049(5) 0.039(4) 0.039(4) 0.008(3) -0.003(4) -0.009(4) 
C17 0.038(4) 0.063(5) 0.043(4) 0.000(4) -0.001(4) 0.000(5) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Br1 C5 1.938(7) . ? 
O1 C17 1.412(8) . ? 
O2 C4 1.426(7) . ? 
O2 C1 1.453(7) . ? 
O3 C6 1.217(7) . ? 
O4 C7 1.187(8) . ? 
O5 C7 1.343(8) . ? 
O5 C8 1.440(8) . ? 
N C6 1.384(7) . ? 
N C7 1.393(8) . ? 
N C9 1.470(7) . ? 
C1 C17 1.498(9) . ? 
C1 C2 1.508(9) . ? 
C2 C3 1.515(10) . ? 
C3 C4 1.526(9) . ? 
C4 C5 1.538(9) . ? 
C5 C6 1.507(8) . ? 
C8 C9 1.518(9) . ? 
C9 C10 1.531(9) . ? 
C10 C11 1.490(9) . ? 
C11 C12 1.391(9) . ? 
C11 C16 1.393(9) . ? 
C12 C13 1.378(10) . ? 
C13 C14 1.373(9) . ? 
C14 C15 1.372(10) . ? 
C15 C16 1.378(9) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C4 O2 C1 110.3(5) . . ? 
C7 O5 C8 110.5(5) . . ? 
C6 N C7 128.0(6) . . ? 
C6 N C9 120.3(5) . . ? 
C7 N C9 111.0(5) . . ? 
O2 C1 C17 107.9(6) . . ? 
O2 C1 C2 105.8(5) . . ? 
C17 C1 C2 114.1(6) . . ? 
C1 C2 C3 103.9(6) . . ? 
C2 C3 C4 102.2(6) . . ? 
O2 C4 C3 105.9(6) . . ? 
O2 C4 C5 106.9(5) . . ? 
C3 C4 C5 112.7(6) . . ? 
C6 C5 C4 109.7(6) . . ? 
C6 C5 Br1 108.4(5) . . ? 
C4 C5 Br1 109.8(4) . . ? 
O3 C6 N 119.1(6) . . ? 
O3 C6 C5 121.9(6) . . ? 
N C6 C5 119.0(6) . . ? 
O4 C7 O5 122.9(7) . . ? 
O4 C7 N 128.5(7) . . ? 
O5 C7 N 108.6(6) . . ? 
O5 C8 C9 105.3(6) . . ? 
N C9 C8 100.7(5) . . ? 
N C9 C10 112.8(6) . . ? 
C8 C9 C10 114.2(5) . . ? 
C11 C10 C9 115.4(5) . . ? 
C12 C11 C16 117.2(7) . . ? 
C12 C11 C10 121.1(6) . . ? 
C16 C11 C10 121.7(6) . . ? 
C13 C12 C11 121.9(7) . . ? 
C14 C13 C12 120.1(7) . . ? 
C15 C14 C13 118.8(7) . . ? 
C14 C15 C16 121.7(7) . . ? 
C15 C16 C11 120.3(7) . . ? 
O1 C17 C1 112.9(6) . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C4 O2 C1 C17 115.5(6) . . . . ? 
C4 O2 C1 C2 -7.0(7) . . . . ? 
O2 C1 C2 C3 26.0(7) . . . . ? 
C17 C1 C2 C3 -92.4(7) . . . . ? 
C1 C2 C3 C4 -34.0(7) . . . . ? 
C1 O2 C4 C3 -14.9(7) . . . . ? 
C1 O2 C4 C5 105.6(6) . . . . ? 
C2 C3 C4 O2 30.4(7) . . . . ? 
C2 C3 C4 C5 -86.2(7) . . . . ? 
O2 C4 C5 C6 46.2(7) . . . . ? 
C3 C4 C5 C6 162.2(6) . . . . ? 
O2 C4 C5 Br1 165.3(4) . . . . ? 
C3 C4 C5 Br1 -78.7(6) . . . . ? 
C7 N C6 O3 177.7(7) . . . . ? 
C9 N C6 O3 8.4(10) . . . . ? 
C7 N C6 C5 -3.2(10) . . . . ? 
C9 N C6 C5 -172.5(6) . . . . ? 
C4 C5 C6 O3 59.5(9) . . . . ? 
Br1 C5 C6 O3 -60.4(8) . . . . ? 
C4 C5 C6 N -119.5(6) . . . . ? 
Br1 C5 C6 N 120.5(5) . . . . ? 
C8 O5 C7 O4 -172.2(8) . . . . ? 
C8 O5 C7 N 9.2(8) . . . . ? 
C6 N C7 O4 15.7(13) . . . . ? 
C9 N C7 O4 -174.2(8) . . . . ? 
C6 N C7 O5 -165.9(6) . . . . ? 
C9 N C7 O5 4.2(8) . . . . ? 
C7 O5 C8 C9 -18.4(8) . . . . ? 
C6 N C9 C8 156.4(6) . . . . ? 
C7 N C9 C8 -14.6(7) . . . . ? 
C6 N C9 C10 -81.5(7) . . . . ? 
C7 N C9 C10 107.5(6) . . . . ? 
O5 C8 C9 N 19.0(7) . . . . ? 
O5 C8 C9 C10 -102.1(7) . . . . ? 
N C9 C10 C11 -60.9(7) . . . . ? 
C8 C9 C10 C11 53.3(8) . . . . ? 
C9 C10 C11 C12 85.5(8) . . . . ? 
C9 C10 C11 C16 -94.5(7) . . . . ? 
C16 C11 C12 C13 0.4(10) . . . . ? 
C10 C11 C12 C13 -179.6(6) . . . . ? 
C11 C12 C13 C14 0.9(11) . . . . ? 
C12 C13 C14 C15 -2.3(11) . . . . ? 
C13 C14 C15 C16 2.6(11) . . . . ? 
C14 C15 C16 C11 -1.3(11) . . . . ? 
C12 C11 C16 C15 -0.2(10) . . . . ? 
C10 C11 C16 C15 179.8(6) . . . . ? 
O2 C1 C17 O1 58.6(8) . . . . ? 
C2 C1 C17 O1 175.8(6) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              26.27 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.463 
_refine_diff_density_min   -0.414 
_refine_diff_density_rms    0.099 

#======END

