 
data_k01026 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C17 H23 N3 O5' 
_chemical_formula_weight          349.38 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'    .0033    .0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'    .0000    .0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'    .0061    .0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'    .0106    .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/n'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    7.9260(16) 
_cell_length_b                    8.6400(17) 
_cell_length_c                    26.257(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  93.35(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1795.0(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(1) 
_cell_measurement_reflns_used     10928
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        blocks
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.38 
_exptl_crystal_size_mid           0.36 
_exptl_crystal_size_min           0.26 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.293 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              744 
_exptl_absorpt_coefficient_mu     0.096 
_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       173(1) 
_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 KappaCCD diffractometer' 
_diffrn_measurement_method        'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean  18 
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         <1
_diffrn_reflns_number             7666 
_diffrn_reflns_av_R_equivalents   0.0319 
_diffrn_reflns_av_sigmaI/netI     0.0451 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -31 
_diffrn_reflns_limit_l_max        31 
_diffrn_reflns_theta_min          1.55 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              3065 
_reflns_number_gt                 2381 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Nonius, 1998)' 
_computing_cell_refinement        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction         'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material   'SHELX97-2 (Sheldrick, 1997) and local procedures'
 
_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)+(0.0392P)²+0.8239P] 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        0.0058(13) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3065 
_refine_ls_number_parameters      240 
_refine_ls_number_restraints      416 
_refine_ls_R_factor_all           0.0704 
_refine_ls_R_factor_gt            0.0508 
_refine_ls_wR_factor_ref          0.1169 
_refine_ls_wR_factor_gt           0.1081 
_refine_ls_goodness_of_fit_ref    1.076 
_refine_ls_restrained_S_all       1.010 
_refine_ls_shift/su_max           0.156 
_refine_ls_shift/su_mean          0.020 
 
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 
C1 C 0.7549(3) 1.0654(2) 0.00814(7) 0.0357(5) Uani 1 1 d U . . 
H1A H 0.8299 1.1309 -0.0110 0.054 Uiso 1 1 calc R . . 
H1B H 0.6690 1.1299 0.0231 0.054 Uiso 1 1 calc R . . 
H1C H 0.6996 0.9893 -0.0150 0.054 Uiso 1 1 calc R . . 
N1 N 0.85401(18) 0.98448(17) 0.04889(5) 0.0257(4) Uani 1 1 d U . . 
C2 C 0.7506(2) 0.8843(2) 0.07871(6) 0.0238(4) Uani 1 1 d U . . 
C3 C 0.8583(2) 0.7992(2) 0.12197(7) 0.0253(4) Uani 1 1 d U . . 
H3 H 0.9350 0.7269 0.1046 0.030 Uiso 1 1 calc R . . 
C4 C 0.9736(2) 0.9117(2) 0.15399(7) 0.0298(5) Uani 1 1 d U . . 
C5 C 1.0701(2) 1.0182(2) 0.11857(7) 0.0343(5) Uani 1 1 d U . . 
H5A H 1.1334 1.0970 0.1393 0.041 Uiso 1 1 calc R . . 
H5B H 1.1529 0.9560 0.1005 0.041 Uiso 1 1 calc R . . 
C6 C 0.9515(2) 1.0980(2) 0.07997(7) 0.0314(5) Uani 1 1 d U . . 
H6A H 0.8732 1.1655 0.0979 0.038 Uiso 1 1 calc R . . 
H6B H 1.0174 1.1640 0.0575 0.038 Uiso 1 1 calc R . . 
C7 C 0.6657(2) 0.7565(2) 0.04494(7) 0.0260(4) Uani 1 1 d U . . 
O7 O 0.52610(16) 0.70994(15) 0.05167(5) 0.0333(4) Uani 1 1 d U . . 
O8 O 0.76723(15) 0.70375(15) 0.01060(5) 0.0322(4) Uani 1 1 d U . . 
C8 C 0.6995(3) 0.5717(2) -0.01932(8) 0.0392(5) Uani 1 1 d U . . 
H8A H 0.5868 0.5979 -0.0352 0.047 Uiso 1 1 calc R . . 
H8B H 0.6872 0.4811 0.0032 0.047 Uiso 1 1 calc R . . 
C9 C 0.8170(3) 0.5347(3) -0.05925(9) 0.0591(7) Uani 1 1 d U . . 
H9A H 0.7732 0.4463 -0.0794 0.089 Uiso 1 1 calc R . . 
H9B H 0.9281 0.5086 -0.0432 0.089 Uiso 1 1 calc R . . 
H9C H 0.8275 0.6245 -0.0816 0.089 Uiso 1 1 calc R . . 
C10 C 0.6080(2) 0.9731(2) 0.10014(7) 0.0267(4) Uani 1 1 d U . . 
N10 N 0.5026(2) 1.0501(2) 0.11382(7) 0.0415(5) Uani 1 1 d U . . 
C11 C 0.7501(2) 0.6990(2) 0.15531(7) 0.0306(5) Uani 1 1 d U . . 
H11A H 0.8070 0.6925 0.1898 0.037 Uiso 1 1 calc R . . 
H11B H 0.6403 0.7515 0.1586 0.037 Uiso 1 1 calc R . . 
C12 C 0.7162(2) 0.5358(2) 0.13596(7) 0.0308(5) Uani 1 1 d U . . 
O12 O 0.79999(19) 0.47833(16) 0.10385(6) 0.0468(4) Uani 1 1 d U . . 
C13 C 0.5773(3) 0.4510(3) 0.15956(8) 0.0456(6) Uani 1 1 d U . . 
H13A H 0.5660 0.3475 0.1445 0.068 Uiso 1 1 calc R . . 
H13B H 0.4711 0.5079 0.1534 0.068 Uiso 1 1 calc R . . 
H13C H 0.6033 0.4417 0.1964 0.068 Uiso 1 1 calc R . . 
C14 C 0.8750(3) 1.0067(2) 0.18846(7) 0.0316(5) Uani 1 1 d U . . 
N14 N 0.7981(2) 1.0815(2) 0.21445(7) 0.0447(5) Uani 1 1 d U . . 
C15 C 1.1090(3) 0.8189(3) 0.18485(8) 0.0418(5) Uani 1 1 d U A . 
O15 O 1.1753(2) 0.7080(2) 0.16859(7) 0.0807(7) Uani 1 1 d U . . 
O16 O 1.1478(2) 0.8827(2) 0.22954(6) 0.0593(5) Uani 1 1 d DU . . 
C16 C 1.2864(10) 0.8240(12) 0.2644(4) 0.069(2) Uani 0.668(14) 1 d PDU A 1 
H16A H 1.2671 0.8524 0.3001 0.083 Uiso 0.668(14) 1 calc PR A 1 
H16B H 1.2943 0.7098 0.2621 0.083 Uiso 0.668(14) 1 calc PR A 1 
C17 C 1.4416(5) 0.8966(6) 0.2480(3) 0.0587(17) Uani 0.668(14) 1 d PDU A 1 
H17A H 1.5379 0.8624 0.2703 0.088 Uiso 0.668(14) 1 calc PR A 1 
H17B H 1.4310 1.0094 0.2501 0.088 Uiso 0.668(14) 1 calc PR A 1 
H17C H 1.4594 0.8664 0.2128 0.088 Uiso 0.668(14) 1 calc PR A 1 
C16' C 1.297(2) 0.798(2) 0.2527(10) 0.069(2) Uani 0.332(14) 1 d PDU A 2 
H16C H 1.2579 0.7128 0.2745 0.083 Uiso 0.332(14) 1 calc PR A 2 
H16D H 1.3612 0.7509 0.2254 0.083 Uiso 0.332(14) 1 calc PR A 2 
C17' C 1.404(2) 0.8981(12) 0.2824(8) 0.087(6) Uani 0.332(14) 1 d PDU A 2 
H17D H 1.4964 0.8386 0.2991 0.130 Uiso 0.332(14) 1 calc PR A 2 
H17E H 1.3385 0.9484 0.3083 0.130 Uiso 0.332(14) 1 calc PR A 2 
H17F H 1.4498 0.9770 0.2603 0.130 Uiso 0.332(14) 1 calc PR A 2 
 
 
_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 
C1 N1 1.467(2) . ? 
C1 H1A 0.9800 . ? 
C1 H1B 0.9800 . ? 
C1 H1C 0.9800 . ? 
N1 C2 1.452(2) . ? 
N1 C6 1.467(2) . ? 
C2 C10 1.502(3) . ? 
C2 C7 1.545(2) . ? 
C2 C3 1.564(2) . ? 
C3 C11 1.529(3) . ? 
C3 C4 1.549(2) . ? 
C3 H3 1.0000 . ? 
C4 C14 1.478(3) . ? 
C4 C15 1.533(3) . ? 
C4 C5 1.542(3) . ? 
C5 C6 1.509(3) . ? 
C5 H5A 0.9900 . ? 
C5 H5B 0.9900 . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 O7 1.200(2) . ? 
C7 O8 1.324(2) . ? 
O8 C8 1.469(2) . ? 
C8 C9 1.478(3) . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
C10 N10 1.142(2) . ? 
C11 C12 1.517(3) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 O12 1.210(2) . ? 
C12 C13 1.488(3) . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
C14 N14 1.142(2) . ? 
C15 O15 1.184(3) . ? 
C15 O16 1.317(2) . ? 
O16 C16 1.478(6) . ? 
O16 C16' 1.492(13) . ? 
C16 C17 1.467(10) . ? 
C16 H16A 0.9900 . ? 
C16 H16B 0.9900 . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C17 H17C 0.9800 . ? 
C16' C17' 1.414(14) . ? 
C16' H16C 0.9900 . ? 
C16' H16D 0.9900 . ? 
C17' H17D 0.9800 . ? 
C17' H17E 0.9800 . ? 
C17' H17F 0.9800 . ? 
 
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 
N1 C1 H1A 109.5 . . ? 
N1 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
N1 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
C2 N1 C1 112.46(14) . . ? 
C2 N1 C6 113.22(14) . . ? 
C1 N1 C6 109.24(14) . . ? 
N1 C2 C10 110.99(15) . . ? 
N1 C2 C7 110.93(14) . . ? 
C10 C2 C7 105.52(14) . . ? 
N1 C2 C3 111.77(14) . . ? 
C10 C2 C3 111.01(14) . . ? 
C7 C2 C3 106.36(14) . . ? 
C11 C3 C4 112.18(15) . . ? 
C11 C3 C2 112.45(15) . . ? 
C4 C3 C2 112.25(15) . . ? 
C11 C3 H3 106.5 . . ? 
C4 C3 H3 106.5 . . ? 
C2 C3 H3 106.5 . . ? 
C14 C4 C15 110.21(16) . . ? 
C14 C4 C5 109.68(16) . . ? 
C15 C4 C5 105.91(16) . . ? 
C14 C4 C3 111.36(15) . . ? 
C15 C4 C3 109.35(16) . . ? 
C5 C4 C3 110.19(15) . . ? 
C6 C5 C4 111.48(15) . . ? 
C6 C5 H5A 109.3 . . ? 
C4 C5 H5A 109.3 . . ? 
C6 C5 H5B 109.3 . . ? 
C4 C5 H5B 109.3 . . ? 
H5A C5 H5B 108.0 . . ? 
N1 C6 C5 110.81(15) . . ? 
N1 C6 H6A 109.5 . . ? 
C5 C6 H6A 109.5 . . ? 
N1 C6 H6B 109.5 . . ? 
C5 C6 H6B 109.5 . . ? 
H6A C6 H6B 108.1 . . ? 
O7 C7 O8 125.95(17) . . ? 
O7 C7 C2 121.98(16) . . ? 
O8 C7 C2 112.01(15) . . ? 
C7 O8 C8 114.45(14) . . ? 
O8 C8 C9 108.79(16) . . ? 
O8 C8 H8A 109.9 . . ? 
C9 C8 H8A 109.9 . . ? 
O8 C8 H8B 109.9 . . ? 
C9 C8 H8B 109.9 . . ? 
H8A C8 H8B 108.3 . . ? 
C8 C9 H9A 109.5 . . ? 
C8 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
C8 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
N10 C10 C2 174.5(2) . . ? 
C12 C11 C3 115.38(16) . . ? 
C12 C11 H11A 108.4 . . ? 
C3 C11 H11A 108.4 . . ? 
C12 C11 H11B 108.4 . . ? 
C3 C11 H11B 108.4 . . ? 
H11A C11 H11B 107.5 . . ? 
O12 C12 C13 122.54(18) . . ? 
O12 C12 C11 121.40(18) . . ? 
C13 C12 C11 116.05(17) . . ? 
C12 C13 H13A 109.5 . . ? 
C12 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C12 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
N14 C14 C4 178.9(2) . . ? 
O15 C15 O16 125.0(2) . . ? 
O15 C15 C4 122.99(19) . . ? 
O16 C15 C4 111.86(19) . . ? 
C15 O16 C16 122.3(4) . . ? 
C15 O16 C16' 107.2(9) . . ? 
C16 O16 C16' 15.3(12) . . ? 
C17 C16 O16 106.1(6) . . ? 
C17 C16 H16A 110.4 . . ? 
O16 C16 H16A 110.5 . . ? 
C17 C16 H16B 110.6 . . ? 
O16 C16 H16B 110.6 . . ? 
H16A C16 H16B 108.7 . . ? 
C16 C17 H17A 109.5 . . ? 
C16 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
C16 C17 H17C 109.4 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
C17' C16' O16 110.8(12) . . ? 
C17' C16' H16C 109.4 . . ? 
O16 C16' H16C 109.5 . . ? 
C17' C16' H16D 109.6 . . ? 
O16 C16' H16D 109.5 . . ? 
H16C C16' H16D 108.0 . . ? 
C16' C17' H17D 109.4 . . ? 
C16' C17' H17E 109.6 . . ? 
H17D C17' H17E 109.5 . . ? 
C16' C17' H17F 109.4 . . ? 
H17D C17' H17F 109.5 . . ? 
H17E C17' H17F 109.5 . . ? 
 
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 
C1 N1 C2 C10 -55.44(19) . . . . ? 
C6 N1 C2 C10 68.98(18) . . . . ? 
C1 N1 C2 C7 61.53(19) . . . . ? 
C6 N1 C2 C7 -174.04(14) . . . . ? 
C1 N1 C2 C3 -179.96(14) . . . . ? 
C6 N1 C2 C3 -55.53(19) . . . . ? 
N1 C2 C3 C11 177.33(14) . . . . ? 
C10 C2 C3 C11 52.82(19) . . . . ? 
C7 C2 C3 C11 -61.47(18) . . . . ? 
N1 C2 C3 C4 49.71(19) . . . . ? 
C10 C2 C3 C4 -74.80(18) . . . . ? 
C7 C2 C3 C4 170.90(14) . . . . ? 
C11 C3 C4 C14 -53.9(2) . . . . ? 
C2 C3 C4 C14 73.86(19) . . . . ? 
C11 C3 C4 C15 68.1(2) . . . . ? 
C2 C3 C4 C15 -164.11(16) . . . . ? 
C11 C3 C4 C5 -175.85(16) . . . . ? 
C2 C3 C4 C5 -48.1(2) . . . . ? 
C14 C4 C5 C6 -70.2(2) . . . . ? 
C15 C4 C5 C6 170.89(16) . . . . ? 
C3 C4 C5 C6 52.7(2) . . . . ? 
C2 N1 C6 C5 60.3(2) . . . . ? 
C1 N1 C6 C5 -173.55(15) . . . . ? 
C4 C5 C6 N1 -58.3(2) . . . . ? 
N1 C2 C7 O7 -144.43(17) . . . . ? 
C10 C2 C7 O7 -24.2(2) . . . . ? 
C3 C2 C7 O7 93.8(2) . . . . ? 
N1 C2 C7 O8 38.2(2) . . . . ? 
C10 C2 C7 O8 158.50(15) . . . . ? 
C3 C2 C7 O8 -83.52(17) . . . . ? 
O7 C7 O8 C8 -2.9(3) . . . . ? 
C2 C7 O8 C8 174.36(15) . . . . ? 
C7 O8 C8 C9 174.50(19) . . . . ? 
N1 C2 C10 N10 13(2) . . . . ? 
C7 C2 C10 N10 -107.4(19) . . . . ? 
C3 C2 C10 N10 137.8(19) . . . . ? 
C4 C3 C11 C12 -145.66(16) . . . . ? 
C2 C3 C11 C12 86.7(2) . . . . ? 
C3 C11 C12 O12 16.7(3) . . . . ? 
C3 C11 C12 C13 -164.55(17) . . . . ? 
C15 C4 C14 N14 158(11) . . . . ? 
C5 C4 C14 N14 42(11) . . . . ? 
C3 C4 C14 N14 -80(11) . . . . ? 
C14 C4 C15 O15 160.7(2) . . . . ? 
C5 C4 C15 O15 -80.7(3) . . . . ? 
C3 C4 C15 O15 38.0(3) . . . . ? 
C14 C4 C15 O16 -23.0(2) . . . . ? 
C5 C4 C15 O16 95.6(2) . . . . ? 
C3 C4 C15 O16 -145.67(18) . . . . ? 
O15 C15 O16 C16 2.2(6) . . . . ? 
C4 C15 O16 C16 -174.0(5) . . . . ? 
O15 C15 O16 C16' 4.5(11) . . . . ? 
C4 C15 O16 C16' -171.7(10) . . . . ? 
C15 O16 C16 C17 84.8(8) . . . . ? 
C16' O16 C16 C17 76(5) . . . . ? 
C15 O16 C16' C17' 146(2) . . . . ? 
C16 O16 C16' C17' -41(3) . . . . ? 
 
_diffrn_measured_fraction_theta_max     .969 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full    .969 
_refine_diff_density_max     .285 
_refine_diff_density_min    -.298 
_refine_diff_density_rms     .040 

#===END

 
data_k01110 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C14 H21 N3 O5' 
_chemical_formula_weight          311.34 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'    .0033    .0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'    .0000    .0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'    .0061    .0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'    .0106    .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+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
 
_cell_length_a                    6.5630(4) 
_cell_length_b                    10.7480(6) 
_cell_length_c                    22.4950(12) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1586.78(16) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(1) 
_cell_measurement_reflns_used     41630
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       25.35
 
_exptl_crystal_description        'irregular fractured rod'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.44 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.18 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.303 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              664 
_exptl_absorpt_coefficient_mu     0.100 
_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       173(1) 
_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 KappaCCD diffractometer' 
_diffrn_measurement_method        'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean  18 
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         <1
_diffrn_reflns_number             9541 
_diffrn_reflns_av_R_equivalents   0.0528 
_diffrn_reflns_av_sigmaI/netI     0.0427 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -27 
_diffrn_reflns_limit_l_max        27 
_diffrn_reflns_theta_min          1.81 
_diffrn_reflns_theta_max          25.41 
_reflns_number_total              1702 
_reflns_number_gt                 1492 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Nonius, 1998)' 
_computing_cell_refinement        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction         'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material   'SHELX97-2 (Sheldrick, 1997) and local procedures'
 
_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)+(0.0447P)²+0.1920P] 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(19) 
_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    0.2(17) 
_refine_ls_number_reflns          1702 
_refine_ls_number_parameters      204 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0540 
_refine_ls_R_factor_gt            0.0435 
_refine_ls_wR_factor_ref          0.0897 
_refine_ls_wR_factor_gt           0.0865 
_refine_ls_goodness_of_fit_ref    1.092 
_refine_ls_restrained_S_all       1.092 
_refine_ls_shift/su_max           0.004 
_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 0.2942(3) 0.86638(19) 0.88044(9) 0.0255(5) Uani 1 1 d . . . 
C1 C 0.2348(4) 0.7442(2) 0.85678(12) 0.0326(7) Uani 1 1 d . . . 
H1A H 0.3063 0.6786 0.8787 0.049 Uiso 1 1 calc R . . 
H1B H 0.2711 0.7394 0.8146 0.049 Uiso 1 1 calc R . . 
H1C H 0.0874 0.7331 0.8613 0.049 Uiso 1 1 calc R . . 
C2 C 0.5078(4) 0.8951(2) 0.86994(10) 0.0237(6) Uani 1 1 d . . . 
C3 C 0.5606(4) 1.0286(2) 0.89295(10) 0.0243(6) Uani 1 1 d . . . 
H3 H 0.4773 1.0879 0.8688 0.029 Uiso 1 1 calc R . . 
N4 N 0.4903(4) 1.1893(2) 0.96973(10) 0.0315(5) Uani 1 1 d . . . 
O4A O 0.4883(4) 1.26093(17) 0.92811(9) 0.0534(7) Uani 1 1 d . . . 
O4B O 0.4796(4) 1.22276(18) 1.02129(8) 0.0474(6) Uani 1 1 d . . . 
C4 C 0.4956(4) 1.0468(2) 0.95810(10) 0.0243(6) Uani 1 1 d . . . 
C5 C 0.2743(4) 1.0062(2) 0.96629(11) 0.0294(6) Uani 1 1 d . . . 
H5A H 0.2380 1.0102 1.0090 0.035 Uiso 1 1 calc R . . 
H5B H 0.1835 1.0637 0.9444 0.035 Uiso 1 1 calc R . . 
C6 C 0.2431(4) 0.8743(2) 0.94355(10) 0.0271(6) Uani 1 1 d . . . 
H6A H 0.3302 0.8163 0.9664 0.032 Uiso 1 1 calc R . . 
H6B H 0.0993 0.8495 0.9495 0.032 Uiso 1 1 calc R . . 
O7 O 0.7227(3) 0.85713(17) 0.78542(8) 0.0394(5) Uani 1 1 d . . . 
C7 C 0.5604(5) 0.8928(2) 0.80297(11) 0.0279(7) Uani 1 1 d . . . 
O8 O 0.4121(3) 0.93807(16) 0.77032(7) 0.0333(5) Uani 1 1 d . . . 
C8 C 0.4530(6) 0.9435(3) 0.70634(11) 0.0464(9) Uani 1 1 d . . . 
H8A H 0.4984 0.8613 0.6916 0.056 Uiso 1 1 calc R . . 
H8B H 0.5607 1.0054 0.6977 0.056 Uiso 1 1 calc R . . 
C9 C 0.2577(7) 0.9804(3) 0.67745(14) 0.0681(12) Uani 1 1 d . . . 
H9A H 0.2214 1.0650 0.6897 0.102 Uiso 1 1 calc R . . 
H9B H 0.1497 0.9227 0.6895 0.102 Uiso 1 1 calc R . . 
H9C H 0.2737 0.9776 0.6342 0.102 Uiso 1 1 calc R . . 
N10 N 0.7318(4) 0.7215(2) 0.92082(9) 0.0358(6) Uani 1 1 d . . . 
C10 C 0.6422(4) 0.7990(2) 0.89769(11) 0.0257(6) Uani 1 1 d . . . 
C11 C 0.7840(4) 1.0627(2) 0.88200(11) 0.0265(6) Uani 1 1 d . . . 
H11A H 0.8318 1.1153 0.9153 0.032 Uiso 1 1 calc R . . 
H11B H 0.8660 0.9854 0.8823 0.032 Uiso 1 1 calc R . . 
O12 O 0.6891(3) 1.15899(16) 0.79054(8) 0.0365(5) Uani 1 1 d . . . 
C12 C 0.8245(4) 1.1308(2) 0.82434(12) 0.0292(6) Uani 1 1 d . . . 
C13 C 1.0433(5) 1.1618(3) 0.81277(14) 0.0514(9) Uani 1 1 d . . . 
H13A H 1.0537 1.2114 0.7763 0.077 Uiso 1 1 calc R . . 
H13B H 1.1216 1.0848 0.8081 0.077 Uiso 1 1 calc R . . 
H13C H 1.0979 1.2096 0.8463 0.077 Uiso 1 1 calc R . . 
C14 C 0.6347(4) 0.9911(2) 1.00498(11) 0.0314(7) Uani 1 1 d . . . 
H14A H 0.7715 1.0266 1.0009 0.047 Uiso 1 1 calc R . . 
H14B H 0.6413 0.9007 0.9997 0.047 Uiso 1 1 calc R . . 
H14C H 0.5809 1.0101 1.0446 0.047 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 C2 1.455(3) . ? 
N1 C6 1.461(3) . ? 
N1 C1 1.470(3) . ? 
C1 H1A 0.9800 . ? 
C1 H1B 0.9800 . ? 
C1 H1C 0.9800 . ? 
C2 C10 1.495(4) . ? 
C2 C7 1.546(3) . ? 
C2 C3 1.564(3) . ? 
C3 C11 1.531(4) . ? 
C3 C4 1.539(3) . ? 
C3 H3 1.0000 . ? 
N4 O4A 1.212(3) . ? 
N4 O4B 1.216(3) . ? 
N4 C4 1.555(3) . ? 
C4 C14 1.518(4) . ? 
C4 C5 1.528(4) . ? 
C5 C6 1.521(3) . ? 
C5 H5A 0.9900 . ? 
C5 H5B 0.9900 . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
O7 C7 1.199(3) . ? 
C7 O8 1.313(3) . ? 
O8 C8 1.465(3) . ? 
C8 C9 1.491(5) . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
N10 C10 1.145(3) . ? 
C11 C12 1.513(3) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
O12 C12 1.208(3) . ? 
C12 C13 1.497(4) . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
C14 H14A 0.9800 . ? 
C14 H14B 0.9800 . ? 
C14 H14C 0.9800 . ? 
 
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 
C2 N1 C6 111.5(2) . . ? 
C2 N1 C1 112.8(2) . . ? 
C6 N1 C1 110.06(19) . . ? 
N1 C1 H1A 109.5 . . ? 
N1 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
N1 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
N1 C2 C10 110.7(2) . . ? 
N1 C2 C7 111.7(2) . . ? 
C10 C2 C7 105.3(2) . . ? 
N1 C2 C3 110.8(2) . . ? 
C10 C2 C3 111.4(2) . . ? 
C7 C2 C3 106.75(19) . . ? 
C11 C3 C4 112.9(2) . . ? 
C11 C3 C2 112.2(2) . . ? 
C4 C3 C2 111.7(2) . . ? 
C11 C3 H3 106.5 . . ? 
C4 C3 H3 106.5 . . ? 
C2 C3 H3 106.5 . . ? 
O4A N4 O4B 123.3(2) . . ? 
O4A N4 C4 119.7(2) . . ? 
O4B N4 C4 116.9(2) . . ? 
C14 C4 C5 112.0(2) . . ? 
C14 C4 C3 116.4(2) . . ? 
C5 C4 C3 110.0(2) . . ? 
C14 C4 N4 106.6(2) . . ? 
C5 C4 N4 103.9(2) . . ? 
C3 C4 N4 106.95(19) . . ? 
C6 C5 C4 110.7(2) . . ? 
C6 C5 H5A 109.5 . . ? 
C4 C5 H5A 109.5 . . ? 
C6 C5 H5B 109.5 . . ? 
C4 C5 H5B 109.5 . . ? 
H5A C5 H5B 108.1 . . ? 
N1 C6 C5 110.5(2) . . ? 
N1 C6 H6A 109.6 . . ? 
C5 C6 H6A 109.6 . . ? 
N1 C6 H6B 109.6 . . ? 
C5 C6 H6B 109.6 . . ? 
H6A C6 H6B 108.1 . . ? 
O7 C7 O8 126.4(2) . . ? 
O7 C7 C2 121.6(3) . . ? 
O8 C7 C2 111.9(2) . . ? 
C7 O8 C8 115.4(2) . . ? 
O8 C8 C9 106.3(3) . . ? 
O8 C8 H8A 110.5 . . ? 
C9 C8 H8A 110.5 . . ? 
O8 C8 H8B 110.5 . . ? 
C9 C8 H8B 110.5 . . ? 
H8A C8 H8B 108.7 . . ? 
C8 C9 H9A 109.5 . . ? 
C8 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
C8 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
N10 C10 C2 174.7(3) . . ? 
C12 C11 C3 114.9(2) . . ? 
C12 C11 H11A 108.5 . . ? 
C3 C11 H11A 108.5 . . ? 
C12 C11 H11B 108.5 . . ? 
C3 C11 H11B 108.5 . . ? 
H11A C11 H11B 107.5 . . ? 
O12 C12 C13 122.7(3) . . ? 
O12 C12 C11 122.1(2) . . ? 
C13 C12 C11 115.1(3) . . ? 
C12 C13 H13A 109.5 . . ? 
C12 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C12 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C4 C14 H14A 109.5 . . ? 
C4 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C4 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
 
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 
C6 N1 C2 C10 65.6(3) . . . . ? 
C1 N1 C2 C10 -58.8(3) . . . . ? 
C6 N1 C2 C7 -177.4(2) . . . . ? 
C1 N1 C2 C7 58.2(3) . . . . ? 
C6 N1 C2 C3 -58.5(2) . . . . ? 
C1 N1 C2 C3 177.07(19) . . . . ? 
N1 C2 C3 C11 -179.4(2) . . . . ? 
C10 C2 C3 C11 56.9(3) . . . . ? 
C7 C2 C3 C11 -57.5(3) . . . . ? 
N1 C2 C3 C4 52.7(3) . . . . ? 
C10 C2 C3 C4 -71.0(3) . . . . ? 
C7 C2 C3 C4 174.5(2) . . . . ? 
C11 C3 C4 C14 -48.9(3) . . . . ? 
C2 C3 C4 C14 78.7(3) . . . . ? 
C11 C3 C4 C5 -177.7(2) . . . . ? 
C2 C3 C4 C5 -50.1(3) . . . . ? 
C11 C3 C4 N4 70.1(3) . . . . ? 
C2 C3 C4 N4 -162.3(2) . . . . ? 
O4A N4 C4 C14 141.6(3) . . . . ? 
O4B N4 C4 C14 -41.4(3) . . . . ? 
O4A N4 C4 C5 -99.9(3) . . . . ? 
O4B N4 C4 C5 77.1(3) . . . . ? 
O4A N4 C4 C3 16.4(4) . . . . ? 
O4B N4 C4 C3 -166.6(2) . . . . ? 
C14 C4 C5 C6 -77.7(3) . . . . ? 
C3 C4 C5 C6 53.5(3) . . . . ? 
N4 C4 C5 C6 167.71(19) . . . . ? 
C2 N1 C6 C5 62.5(3) . . . . ? 
C1 N1 C6 C5 -171.6(2) . . . . ? 
C4 C5 C6 N1 -59.6(3) . . . . ? 
N1 C2 C7 O7 -145.0(2) . . . . ? 
C10 C2 C7 O7 -24.7(3) . . . . ? 
C3 C2 C7 O7 93.8(3) . . . . ? 
N1 C2 C7 O8 37.6(3) . . . . ? 
C10 C2 C7 O8 157.8(2) . . . . ? 
C3 C2 C7 O8 -83.7(3) . . . . ? 
O7 C7 O8 C8 0.5(4) . . . . ? 
C2 C7 O8 C8 177.8(2) . . . . ? 
C7 O8 C8 C9 172.3(2) . . . . ? 
N1 C2 C10 N10 -6(3) . . . . ? 
C7 C2 C10 N10 -127(3) . . . . ? 
C3 C2 C10 N10 118(3) . . . . ? 
C4 C3 C11 C12 -140.0(2) . . . . ? 
C2 C3 C11 C12 92.7(2) . . . . ? 
C3 C11 C12 O12 2.0(4) . . . . ? 
C3 C11 C12 C13 -178.7(2) . . . . ? 
 
_diffrn_measured_fraction_theta_max     .998 
_diffrn_reflns_theta_full              25.41 
_diffrn_measured_fraction_theta_full    .998 
_refine_diff_density_max     .165 
_refine_diff_density_min    -.163 
_refine_diff_density_rms     .037 


#===END

 
data_k00006 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H25 F3 N2 O8' 
_chemical_formula_weight          478.42 
 
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' 
 'F'  'F'   0.0171   0.0103 
 '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            ? 
_symmetry_space_group_name_H-M    ? 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z+1/2' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
 
_cell_length_a                    29.928(4) 
_cell_length_b                    9.4450(10) 
_cell_length_c                    18.951(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  120.430(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      4619.0(11) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.44 
_exptl_crystal_size_mid           0.40 
_exptl_crystal_size_min           0.13 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.376 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              2000 
_exptl_absorpt_coefficient_mu     0.121 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   0.9486 
_exptl_absorpt_correction_T_max   0.9844 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71070 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             7128 
_diffrn_reflns_av_R_equivalents   0.0224 
_diffrn_reflns_av_sigmaI/netI     0.0389 
_diffrn_reflns_limit_h_min        -35 
_diffrn_reflns_limit_h_max        35 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          1.58 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              4082 
_reflns_number_gt                 3065 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_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)+(0.0550P)²+4.9000P] 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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          4082 
_refine_ls_number_parameters      316 
_refine_ls_number_restraints      3 
_refine_ls_R_factor_all           0.0705 
_refine_ls_R_factor_gt            0.0497 
_refine_ls_wR_factor_ref          0.1301 
_refine_ls_wR_factor_gt           0.1181 
_refine_ls_goodness_of_fit_ref    1.030 
_refine_ls_restrained_S_all       1.033 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
F009 F 0.20854(6) 0.0997(2) 0.92821(8) 0.0713(5) Uani 1 1 d . A . 
F010 F 0.13610(6) 0.1387(2) 0.92168(9) 0.0731(5) Uani 1 1 d . A . 
F011 F 0.17060(7) 0.29894(18) 0.88538(10) 0.0732(5) Uani 1 1 d . A . 
O007 O 0.09357(6) 0.03311(19) 0.77824(10) 0.0485(5) Uani 1 1 d . . . 
O009 O 0.16546(6) -0.13900(16) 0.73006(9) 0.0388(4) Uani 1 1 d . A . 
O010 O 0.11670(5) -0.14208(16) 0.59309(9) 0.0367(4) Uani 1 1 d . A . 
O012 O 0.03242(6) -0.02374(19) 0.59941(10) 0.0488(5) Uani 1 1 d . . . 
O013 O 0.04667(5) 0.20408(18) 0.63800(10) 0.0458(4) Uani 1 1 d D . . 
O016 O 0.07504(8) 0.3678(2) 0.47531(11) 0.0675(6) Uani 1 1 d . A . 
O019 O 0.19444(7) 0.44051(19) 0.59559(11) 0.0568(5) Uani 1 1 d . A . 
O020 O 0.18372(6) 0.26703(16) 0.50749(9) 0.0410(4) Uani 1 1 d . A . 
N001 N 0.14909(6) 0.13468(19) 0.74447(10) 0.0288(4) Uani 1 1 d . . . 
N018 N 0.22989(8) -0.0298(3) 0.62253(14) 0.0528(6) Uani 1 1 d . A . 
C002 C 0.11955(7) 0.0739(2) 0.66099(12) 0.0275(5) Uani 1 1 d . A . 
C003 C 0.12624(7) 0.1713(2) 0.60006(12) 0.0271(5) Uani 1 1 d . . . 
H003 H 0.1116 0.2650 0.6026 0.033 Uiso 1 1 calc R A . 
C004 C 0.18401(8) 0.2011(2) 0.62881(12) 0.0323(5) Uani 1 1 d . A . 
C005 C 0.21030(10) 0.2626(4) 0.71674(15) 0.0328(8) Uani 0.866(7) 1 d P A 1 
H05A H 0.2476 0.2783 0.7369 0.039 Uiso 0.866(7) 1 calc PR A 1 
H05B H 0.1945 0.3553 0.7155 0.039 Uiso 0.866(7) 1 calc PR A 1 
C006 C 0.20475(9) 0.1659(3) 0.77409(15) 0.0335(9) Uani 0.866(7) 1 d P A 1 
H06A H 0.2207 0.2103 0.8289 0.040 Uiso 0.866(7) 1 calc PR A 1 
H06B H 0.2233 0.0763 0.7793 0.040 Uiso 0.866(7) 1 calc PR A 1 
C007 C 0.13222(8) 0.1014(2) 0.79636(13) 0.0341(5) Uani 1 1 d . A . 
C008 C 0.16267(10) 0.1610(3) 0.88374(15) 0.0474(6) Uani 1 1 d . . . 
C009 C 0.13682(8) -0.0816(2) 0.66607(13) 0.0299(5) Uani 1 1 d . . . 
C010 C 0.12643(10) -0.2943(3) 0.59329(16) 0.0470(6) Uani 1 1 d . . . 
H10A H 0.1630 -0.3151 0.6347 0.056 Uiso 1 1 calc R A . 
H10B H 0.1206 -0.3229 0.5390 0.056 Uiso 1 1 calc R . . 
C011 C 0.09119(12) -0.3769(3) 0.61247(19) 0.0676(8) Uani 1 1 d . A . 
H11A H 0.0981 -0.4783 0.6124 0.101 Uiso 1 1 calc R . . 
H11B H 0.0551 -0.3571 0.5711 0.101 Uiso 1 1 calc R . . 
H11C H 0.0973 -0.3494 0.6665 0.101 Uiso 1 1 calc R . . 
C012 C 0.06086(8) 0.0748(3) 0.63070(13) 0.0364(6) Uani 1 1 d . A . 
C013 C -0.00749(10) 0.2116(4) 0.6196(2) 0.0495(11) Uani 0.834(8) 1 d P B 1 
H13A H -0.0129 0.1477 0.6560 0.059 Uiso 0.834(8) 1 calc PR B 1 
H13B H -0.0318 0.1847 0.5621 0.059 Uiso 0.834(8) 1 calc PR B 1 
C014 C -0.01524(13) 0.3614(5) 0.6343(2) 0.0673(14) Uani 0.834(8) 1 d P B 1 
H14A H -0.0508 0.3744 0.6228 0.101 Uiso 0.834(8) 1 calc PR B 1 
H14B H -0.0092 0.4229 0.5984 0.101 Uiso 0.834(8) 1 calc PR B 1 
H14C H 0.0091 0.3859 0.6915 0.101 Uiso 0.834(8) 1 calc PR B 1 
C015 C 0.09362(8) 0.1244(2) 0.51035(12) 0.0317(5) Uani 1 1 d . A . 
H15A H 0.1155 0.0669 0.4960 0.038 Uiso 1 1 calc R . . 
H15B H 0.0649 0.0636 0.5042 0.038 Uiso 1 1 calc R . . 
C016 C 0.07125(8) 0.2466(3) 0.45149(13) 0.0410(6) Uani 1 1 d . . . 
C017 C 0.04338(9) 0.2121(3) 0.36197(13) 0.0483(7) Uani 1 1 d . A . 
H17A H 0.0306 0.2996 0.3301 0.072 Uiso 1 1 calc R . . 
H17B H 0.0141 0.1494 0.3488 0.072 Uiso 1 1 calc R . . 
H17C H 0.0672 0.1645 0.3485 0.072 Uiso 1 1 calc R . . 
C018 C 0.20977(8) 0.0716(3) 0.62346(13) 0.0371(6) Uani 1 1 d . . . 
C019 C 0.18818(8) 0.3182(3) 0.57631(14) 0.0382(6) Uani 1 1 d . . . 
C020 C 0.18432(11) 0.3746(3) 0.45174(16) 0.0543(7) Uani 1 1 d . . . 
H20A H 0.2185 0.4222 0.4774 0.065 Uiso 1 1 calc R A . 
H20B H 0.1574 0.4471 0.4391 0.065 Uiso 1 1 calc R . . 
C021 C 0.17402(11) 0.3012(3) 0.37630(15) 0.0586(8) Uani 1 1 d . A . 
H21A H 0.1735 0.3704 0.3373 0.088 Uiso 1 1 calc R . . 
H21B H 0.1404 0.2532 0.3520 0.088 Uiso 1 1 calc R . . 
H21C H 0.2013 0.2313 0.3894 0.088 Uiso 1 1 calc R . . 
C05B C 0.2189(6) 0.184(2) 0.7260(10) 0.024(5) Uiso 0.134(7) 1 d PD A 2 
C06B C 0.1850(6) 0.2528(19) 0.7554(9) 0.027(5) Uiso 0.134(7) 1 d PD A 2 
C13B C -0.0074(5) 0.2759(18) 0.5877(9) 0.038(5) Uiso 0.166(8) 1 d PD B 2 
C14B C -0.0213(8) 0.271(3) 0.6550(12) 0.072(7) Uiso 0.166(8) 1 d PD B 2 
 
 
_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 
F009 C008 1.326(3) . ? 
F010 C008 1.331(3) . ? 
F011 C008 1.322(3) . ? 
O007 C007 1.212(3) . ? 
O009 C009 1.203(2) . ? 
O010 C009 1.326(3) . ? 
O010 C010 1.466(3) . ? 
O012 C012 1.196(3) . ? 
O013 C012 1.323(3) . ? 
O013 C013 1.477(3) . ? 
O013 C13B 1.557(12) . ? 
O016 C016 1.214(3) . ? 
O019 C019 1.198(3) . ? 
O020 C019 1.333(3) . ? 
O020 C020 1.473(3) . ? 
N001 C007 1.350(3) . ? 
N001 C002 1.482(2) . ? 
N001 C06B 1.489(16) . ? 
N001 C006 1.493(3) . ? 
N018 C018 1.136(3) . ? 
C002 C009 1.543(3) . ? 
C002 C012 1.547(3) . ? 
C002 C003 1.567(3) . ? 
C003 C015 1.535(3) . ? 
C003 C004 1.553(3) . ? 
C003 H003 1.0000 . ? 
C004 C018 1.477(4) . ? 
C004 C019 1.534(3) . ? 
C004 C005 1.551(3) . ? 
C004 C05B 1.600(17) . ? 
C005 C006 1.492(4) . ? 
C005 H05A 0.9900 . ? 
C005 H05B 0.9900 . ? 
C006 H06A 0.9900 . ? 
C006 H06B 0.9900 . ? 
C007 C008 1.537(3) . ? 
C010 C011 1.497(4) . ? 
C010 H10A 0.9900 . ? 
C010 H10B 0.9900 . ? 
C011 H11A 0.9800 . ? 
C011 H11B 0.9800 . ? 
C011 H11C 0.9800 . ? 
C013 C014 1.483(5) . ? 
C013 H13A 0.9900 . ? 
C013 H13B 0.9900 . ? 
C014 H14A 0.9800 . ? 
C014 H14B 0.9800 . ? 
C014 H14C 0.9800 . ? 
C015 C016 1.506(3) . ? 
C015 H15A 0.9900 . ? 
C015 H15B 0.9900 . ? 
C016 C017 1.499(3) . ? 
C017 H17A 0.9800 . ? 
C017 H17B 0.9800 . ? 
C017 H17C 0.9800 . ? 
C020 C021 1.474(4) . ? 
C020 H20A 0.9900 . ? 
C020 H20B 0.9900 . ? 
C021 H21A 0.9800 . ? 
C021 H21B 0.9800 . ? 
C021 H21C 0.9800 . ? 
C05B C06B 1.527(17) . ? 
C13B C14B 1.529(18) . ? 
 
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 
C009 O010 C010 115.79(18) . . ? 
C012 O013 C013 113.1(2) . . ? 
C012 O013 C13B 128.9(6) . . ? 
C013 O013 C13B 32.7(6) . . ? 
C019 O020 C020 114.86(19) . . ? 
C007 N001 C002 116.50(17) . . ? 
C007 N001 C06B 125.7(6) . . ? 
C002 N001 C06B 115.9(6) . . ? 
C007 N001 C006 121.98(17) . . ? 
C002 N001 C006 115.23(16) . . ? 
C06B N001 C006 37.8(6) . . ? 
N001 C002 C009 107.59(16) . . ? 
N001 C002 C012 110.18(16) . . ? 
C009 C002 C012 108.05(17) . . ? 
N001 C002 C003 109.24(16) . . ? 
C009 C002 C003 116.16(17) . . ? 
C012 C002 C003 105.55(16) . . ? 
C015 C003 C004 114.30(17) . . ? 
C015 C003 C002 113.58(17) . . ? 
C004 C003 C002 112.53(16) . . ? 
C015 C003 H003 105.1 . . ? 
C004 C003 H003 105.1 . . ? 
C002 C003 H003 105.1 . . ? 
C018 C004 C019 109.60(18) . . ? 
C018 C004 C005 112.7(2) . . ? 
C019 C004 C005 105.3(2) . . ? 
C018 C004 C003 110.67(18) . . ? 
C019 C004 C003 110.18(17) . . ? 
C005 C004 C003 108.30(17) . . ? 
C018 C004 C05B 86.4(7) . . ? 
C019 C004 C05B 126.8(7) . . ? 
C005 C004 C05B 28.5(6) . . ? 
C003 C004 C05B 110.3(6) . . ? 
C006 C005 C004 111.7(2) . . ? 
C006 C005 H05A 109.3 . . ? 
C004 C005 H05A 109.3 . . ? 
C006 C005 H05B 109.3 . . ? 
C004 C005 H05B 109.3 . . ? 
H05A C005 H05B 107.9 . . ? 
C005 C006 N001 111.2(2) . . ? 
C005 C006 H06A 109.4 . . ? 
N001 C006 H06A 109.4 . . ? 
C005 C006 H06B 109.4 . . ? 
N001 C006 H06B 109.4 . . ? 
H06A C006 H06B 108.0 . . ? 
O007 C007 N001 124.9(2) . . ? 
O007 C007 C008 117.4(2) . . ? 
N001 C007 C008 117.59(19) . . ? 
F011 C008 F009 107.4(2) . . ? 
F011 C008 F010 107.0(2) . . ? 
F009 C008 F010 107.3(2) . . ? 
F011 C008 C007 112.8(2) . . ? 
F009 C008 C007 112.5(2) . . ? 
F010 C008 C007 109.5(2) . . ? 
O009 C009 O010 124.9(2) . . ? 
O009 C009 C002 122.49(19) . . ? 
O010 C009 C002 112.59(18) . . ? 
O010 C010 C011 110.4(2) . . ? 
O010 C010 H10A 109.6 . . ? 
C011 C010 H10A 109.6 . . ? 
O010 C010 H10B 109.6 . . ? 
C011 C010 H10B 109.6 . . ? 
H10A C010 H10B 108.1 . . ? 
C010 C011 H11A 109.5 . . ? 
C010 C011 H11B 109.5 . . ? 
H11A C011 H11B 109.5 . . ? 
C010 C011 H11C 109.5 . . ? 
H11A C011 H11C 109.5 . . ? 
H11B C011 H11C 109.5 . . ? 
O012 C012 O013 125.78(19) . . ? 
O012 C012 C002 124.6(2) . . ? 
O013 C012 C002 109.31(18) . . ? 
O013 C013 C014 105.0(3) . . ? 
O013 C013 H13A 110.7 . . ? 
C014 C013 H13A 110.7 . . ? 
O013 C013 H13B 110.7 . . ? 
C014 C013 H13B 110.7 . . ? 
H13A C013 H13B 108.8 . . ? 
C013 C014 H14A 109.5 . . ? 
C013 C014 H14B 109.5 . . ? 
H14A C014 H14B 109.5 . . ? 
C013 C014 H14C 109.5 . . ? 
H14A C014 H14C 109.5 . . ? 
H14B C014 H14C 109.5 . . ? 
C016 C015 C003 113.21(18) . . ? 
C016 C015 H15A 108.9 . . ? 
C003 C015 H15A 108.9 . . ? 
C016 C015 H15B 108.9 . . ? 
C003 C015 H15B 108.9 . . ? 
H15A C015 H15B 107.7 . . ? 
O016 C016 C017 121.3(2) . . ? 
O016 C016 C015 121.6(2) . . ? 
C017 C016 C015 117.1(2) . . ? 
C016 C017 H17A 109.5 . . ? 
C016 C017 H17B 109.5 . . ? 
H17A C017 H17B 109.5 . . ? 
C016 C017 H17C 109.5 . . ? 
H17A C017 H17C 109.5 . . ? 
H17B C017 H17C 109.5 . . ? 
N018 C018 C004 177.0(2) . . ? 
O019 C019 O020 124.8(2) . . ? 
O019 C019 C004 123.3(2) . . ? 
O020 C019 C004 111.9(2) . . ? 
O020 C020 C021 107.4(2) . . ? 
O020 C020 H20A 110.2 . . ? 
C021 C020 H20A 110.2 . . ? 
O020 C020 H20B 110.2 . . ? 
C021 C020 H20B 110.2 . . ? 
H20A C020 H20B 108.5 . . ? 
C020 C021 H21A 109.5 . . ? 
C020 C021 H21B 109.5 . . ? 
H21A C021 H21B 109.5 . . ? 
C020 C021 H21C 109.5 . . ? 
H21A C021 H21C 109.5 . . ? 
H21B C021 H21C 109.5 . . ? 
C06B C05B C004 102.1(12) . . ? 
N001 C06B C05B 101.4(13) . . ? 
C14B C13B O013 96.5(13) . . ? 
 
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.318 
_refine_diff_density_min   -0.235 
_refine_diff_density_rms    0.048 


