 
data_compound 20
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H25 N O6'
_chemical_formula_weight          327.37
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 '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+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 
_cell_length_a                    5.593
_cell_length_b                    8.325
_cell_length_c                    36.5860(10)
_cell_angle_alpha                 90.000(2)
_cell_angle_beta                  90.000(3)
_cell_angle_gamma                 90.000(4)
_cell_volume                      1703.51(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     31
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        prismatic
_exptl_crystal_colour             white
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           0.6
_exptl_crystal_size_min           ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.276
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              704
_exptl_absorpt_coefficient_mu     0.811
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   Siemens P4
_diffrn_measurement_method        'profile data from theta\2theta scan'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          3
_diffrn_standards_interval_count  300
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         50
_diffrn_reflns_number             2266
_diffrn_reflns_av_R_equivalents   0.0393
_diffrn_reflns_av_sigmaI/netI     0.0269
_diffrn_reflns_limit_h_min        -1
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -1
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -1
_diffrn_reflns_limit_l_max        42
_diffrn_reflns_theta_min          2.42
_diffrn_reflns_theta_max          64.07
_reflns_number_total              2037
_reflns_number_gt                 1959
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Siemens P4'
_computing_cell_refinement        'Siemens P4'
_computing_data_reduction         'Siemens P4'
_computing_structure_solution     'SIR97 (Altomare, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Ortep3 (Johnson, 1996)'
_computing_publication_material   'CIFTAB'
 
_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
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0744P)²+0.2561P] where P=(Fo²+2Fc²)/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        0.0067(7)
_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    1.1(3)
_refine_ls_number_reflns          2037
_refine_ls_number_parameters      262
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0420
_refine_ls_R_factor_gt            0.0408
_refine_ls_wR_factor_ref          0.1176
_refine_ls_wR_factor_gt           0.1154
_refine_ls_goodness_of_fit_ref    1.057
_refine_ls_restrained_S_all       1.057
_refine_ls_shift/su_max           0.008
_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_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.4997(5) 0.2799(3) 0.88001(5) 0.0658(6) Uani 1 1 d . . .
O1 O 0.7475(4) -0.2365(3) 0.83466(9) 0.1101(10) Uani 1 1 d . . .
O2 O 0.5585(3) -0.0150(2) 0.81691(5) 0.0593(5) Uani 1 1 d . . .
O3 O 0.9257(4) 0.3958(3) 0.77337(5) 0.0765(6) Uani 1 1 d . . .
O4 O 0.5884(3) 0.2499(2) 0.77030(5) 0.0670(5) Uani 1 1 d . . .
O5 O 0.4739(3) 0.3530(2) 0.84409(5) 0.0656(5) Uani 1 1 d . . .
O6 O 0.7931(4) 0.1209(3) 0.94117(5) 0.0790(6) Uani 1 1 d . . .
C1 C 0.3222(5) -0.2384(4) 0.83124(9) 0.0734(8) Uani 1 1 d . . .
H1A H 0.2056 -0.1609 0.8235 0.246(12) Uiso 1 1 calc R . .
H1B H 0.2927 -0.2675 0.8562 0.246(12) Uiso 1 1 calc R . .
H1C H 0.3111 -0.3323 0.8161 0.246(12) Uiso 1 1 calc R . .
C2 C 0.5641(5) -0.1685(3) 0.82799(7) 0.0586(6) Uani 1 1 d . . .
C3 C 0.7835(5) 0.0672(3) 0.81133(7) 0.0557(6) Uani 1 1 d . . .
H3 H 0.919(6) -0.006(4) 0.8101(8) 0.079(9) Uiso 1 1 d . . .
C4 C 0.7764(5) 0.1345(4) 0.77282(7) 0.0624(7) Uani 1 1 d . . .
H4 H 0.757(6) 0.042(4) 0.7550(9) 0.083(9) Uiso 1 1 d . . .
C5 C 0.9968(6) 0.2337(4) 0.76440(8) 0.0711(8) Uani 1 1 d . . .
H5A H 1.037(6) 0.227(4) 0.7391(9) 0.079(9) Uiso 1 1 d . . .
H5B H 1.149(6) 0.200(4) 0.7790(8) 0.077(9) Uiso 1 1 d . . .
C6 C 0.6902(5) 0.3842(3) 0.78742(7) 0.0632(7) Uani 1 1 d . . .
H6 H 0.592(5) 0.485(3) 0.7802(7) 0.061(7) Uiso 1 1 d . . .
C7 C 0.7083(5) 0.3599(3) 0.82848(6) 0.0551(6) Uani 1 1 d . . .
H7 H 0.793(6) 0.452(3) 0.8399(7) 0.065(8) Uiso 1 1 d . . .
C8 C 0.8226(5) 0.2015(3) 0.83956(6) 0.0511(6) Uani 1 1 d . . .
H8 H 0.984(5) 0.217(3) 0.8421(6) 0.048(6) Uiso 1 1 d . . .
C9 C 0.7092(5) 0.1692(3) 0.87732(7) 0.0555(6) Uani 1 1 d . . .
H9 H 0.645(5) 0.061(3) 0.8789(7) 0.061(7) Uiso 1 1 d . . .
C10 C 0.5720(11) 0.4049(4) 0.90722(9) 0.0961(13) Uani 1 1 d . . .
H10A H 0.546(8) 0.500(5) 0.8972(10) 0.091(11) Uiso 1 1 d . . .
H10B H 0.474(8) 0.396(6) 0.9281(13) 0.127(15) Uiso 1 1 d . . .
C11 C 0.8313(10) 0.3842(5) 0.91598(10) 0.0933(12) Uani 1 1 d . . .
H11A H 0.859(8) 0.417(5) 0.9409(12) 0.117(14) Uiso 1 1 d . . .
H11B H 0.930(8) 0.460(5) 0.8989(12) 0.114(13) Uiso 1 1 d . . .
C12 C 0.8719(6) 0.2097(4) 0.90986(7) 0.0697(8) Uani 1 1 d . . .
H12 H 1.053(6) 0.175(4) 0.9035(8) 0.075(8) Uiso 1 1 d . . .
C13 C 0.9536(6) 0.0043(4) 0.95645(8) 0.0789(9) Uani 1 1 d . . .
C14 C 0.8114(9) -0.0685(6) 0.98758(12) 0.1256(17) Uani 1 1 d . . .
H14A H 0.6757 -0.1249 0.9779 0.246(12) Uiso 1 1 calc R . .
H14B H 0.7576 0.0153 1.0036 0.246(12) Uiso 1 1 calc R . .
H14C H 0.9107 -0.1420 1.0009 0.246(12) Uiso 1 1 calc R . .
C15 C 1.1612(8) 0.0902(7) 0.97385(12) 0.1240(16) Uani 1 1 d . . .
H15A H 1.1025 0.1677 0.9911 0.246(12) Uiso 1 1 calc R . .
H15B H 1.2526 0.1440 0.9553 0.246(12) Uiso 1 1 calc R . .
H15C H 1.2609 0.0138 0.9863 0.246(12) Uiso 1 1 calc R . .
C16 C 1.0358(16) -0.1160(6) 0.92929(14) 0.177(3) Uani 1 1 d . . .
H16A H 0.8998 -0.1685 0.9187 0.246(12) Uiso 1 1 calc R . .
H16B H 1.1351 -0.1942 0.9412 0.246(12) Uiso 1 1 calc R . .
H16C H 1.1258 -0.0631 0.9105 0.246(12) Uiso 1 1 calc R . .
 
 
_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
N1 O5 1.456(2) . ?
N1 C9 1.494(3) . ?
N1 C10 1.496(5) . ?
O1 C2 1.197(3) . ?
O2 C2 1.341(3) . ?
O2 C3 1.447(3) . ?
O3 C6 1.417(4) . ?
O3 C5 1.444(4) . ?
O4 C6 1.403(4) . ?
O4 C4 1.427(3) . ?
O5 C7 1.431(3) . ?
O6 C12 1.432(3) . ?
O6 C13 1.436(4) . ?
C1 C2 1.478(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C4 1.517(4) . ?
C3 C8 1.538(4) . ?
C3 H3 0.97(4) . ?
C4 C5 1.515(4) . ?
C4 H4 1.01(3) . ?
C5 H5A 0.95(3) . ?
C5 H5B 1.04(3) . ?
C6 C7 1.519(4) . ?
C6 H6 1.04(3) . ?
C7 C8 1.521(3) . ?
C7 H7 0.99(3) . ?
C8 C9 1.544(3) . ?
C8 H8 0.92(3) . ?
C9 C12 1.536(4) . ?
C9 H9 0.97(3) . ?
C10 C11 1.495(7) . ?
C10 H10A 0.89(4) . ?
C10 H10B 0.94(5) . ?
C11 C12 1.488(5) . ?
C11 H11A 0.96(4) . ?
C11 H11B 1.04(5) . ?
C12 H12 1.08(4) . ?
C13 C16 1.484(6) . ?
C13 C15 1.505(6) . ?
C13 C14 1.516(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
 
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
O5 N1 C9 106.04(17) . . ?
O5 N1 C10 109.7(2) . . ?
C9 N1 C10 105.1(3) . . ?
C2 O2 C3 118.2(2) . . ?
C6 O3 C5 106.0(2) . . ?
C6 O4 C4 102.1(2) . . ?
C7 O5 N1 106.62(18) . . ?
C12 O6 C13 117.9(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 122.2(3) . . ?
O1 C2 C1 125.6(2) . . ?
O2 C2 C1 112.2(2) . . ?
O2 C3 C4 106.5(2) . . ?
O2 C3 C8 111.9(2) . . ?
C4 C3 C8 111.0(2) . . ?
O2 C3 H3 113(2) . . ?
C4 C3 H3 102.0(18) . . ?
C8 C3 H3 112.0(19) . . ?
O4 C4 C5 102.7(2) . . ?
O4 C4 C3 109.1(2) . . ?
C5 C4 C3 111.7(2) . . ?
O4 C4 H4 113(2) . . ?
C5 C4 H4 112(2) . . ?
C3 C4 H4 108.8(18) . . ?
O3 C5 C4 103.8(2) . . ?
O3 C5 H5A 110.0(19) . . ?
C4 C5 H5A 111(2) . . ?
O3 C5 H5B 110.9(18) . . ?
C4 C5 H5B 114.6(17) . . ?
H5A C5 H5B 107(3) . . ?
O4 C6 O3 105.6(2) . . ?
O4 C6 C7 111.3(2) . . ?
O3 C6 C7 107.8(2) . . ?
O4 C6 H6 108.4(15) . . ?
O3 C6 H6 110.2(16) . . ?
C7 C6 H6 113.3(14) . . ?
O5 C7 C6 109.8(2) . . ?
O5 C7 C8 104.1(2) . . ?
C6 C7 C8 114.0(2) . . ?
O5 C7 H7 107.4(18) . . ?
C6 C7 H7 110.1(16) . . ?
C8 C7 H7 111.0(17) . . ?
C7 C8 C3 113.1(2) . . ?
C7 C8 C9 102.5(2) . . ?
C3 C8 C9 114.6(2) . . ?
C7 C8 H8 108.4(17) . . ?
C3 C8 H8 108.1(16) . . ?
C9 C8 H8 109.9(15) . . ?
N1 C9 C12 106.1(2) . . ?
N1 C9 C8 105.88(18) . . ?
C12 C9 C8 114.3(2) . . ?
N1 C9 H9 106.1(18) . . ?
C12 C9 H9 112.2(16) . . ?
C8 C9 H9 111.4(15) . . ?
C11 C10 N1 108.9(3) . . ?
C11 C10 H10A 111(3) . . ?
N1 C10 H10A 108(2) . . ?
C11 C10 H10B 112(3) . . ?
N1 C10 H10B 109(3) . . ?
H10A C10 H10B 108(4) . . ?
C12 C11 C10 103.2(4) . . ?
C12 C11 H11A 113(3) . . ?
C10 C11 H11A 109(3) . . ?
C12 C11 H11B 115(2) . . ?
C10 C11 H11B 108(2) . . ?
H11A C11 H11B 108(4) . . ?
O6 C12 C11 109.7(3) . . ?
O6 C12 C9 108.9(2) . . ?
C11 C12 C9 103.9(3) . . ?
O6 C12 H12 109.1(17) . . ?
C11 C12 H12 115.7(18) . . ?
C9 C12 H12 109.3(16) . . ?
O6 C13 C16 112.9(3) . . ?
O6 C13 C15 109.0(3) . . ?
C16 C13 C15 111.4(5) . . ?
O6 C13 C14 103.6(3) . . ?
C16 C13 C14 113.3(4) . . ?
C15 C13 C14 106.1(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.926
_diffrn_reflns_theta_full              64.07
_diffrn_measured_fraction_theta_full   0.926
_refine_diff_density_max    0.182
_refine_diff_density_min   -0.171
_refine_diff_density_rms    0.039
