 
data_cz24 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C21 H21 N3 O9' 
_chemical_formula_weight          459.41 
 
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    P21/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                    7.0804(10) 
_cell_length_b                    10.7575(2) 
_cell_length_c                    25.6538(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  97.0277(7) 
_cell_angle_gamma                 90.00 
_cell_volume                      1939.3(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     423(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.573 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              960 
_exptl_absorpt_coefficient_mu     0.125 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   0.9754 
_exptl_absorpt_correction_T_max   0.9876 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       423(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   ? 
_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             13417 
_diffrn_reflns_av_R_equivalents   0.0271 
_diffrn_reflns_av_sigmaI/netI     0.0289 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -32 
_diffrn_reflns_limit_l_max        32 
_diffrn_reflns_theta_min          3.06 
_diffrn_reflns_theta_max          26.37 
_reflns_number_total              3932 
_reflns_number_gt                 3251 
_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)+(0.0632P)²+0.4954P] 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        0.000(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3932 
_refine_ls_number_parameters      284 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0500 
_refine_ls_R_factor_gt            0.0396 
_refine_ls_wR_factor_ref          0.1162 
_refine_ls_wR_factor_gt           0.1096 
_refine_ls_goodness_of_fit_ref    1.060 
_refine_ls_restrained_S_all       1.060 
_refine_ls_shift/su_max           0.538 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
N1 N 0.23305(14) -0.21990(9) 0.49614(4) 0.0170(2) Uani 1 1 d . . . 
C2 C 0.16231(17) -0.22640(12) 0.44636(5) 0.0170(3) Uani 1 1 d . . . 
C3 C 0.11958(18) -0.12422(12) 0.41175(5) 0.0188(3) Uani 1 1 d . . . 
H3 H 0.0720 -0.1367 0.3767 0.023 Uiso 1 1 calc R . . 
C4 C 0.15066(17) -0.00752(12) 0.43156(5) 0.0172(3) Uani 1 1 d . . . 
C5 C 0.22786(17) 0.00747(12) 0.48557(5) 0.0165(3) Uani 1 1 d . . . 
C6 C 0.26962(17) -0.10236(11) 0.51662(5) 0.0160(3) Uani 1 1 d . . . 
C7 C 0.12388(18) -0.35301(12) 0.42211(5) 0.0199(3) Uani 1 1 d . . . 
O8 O 0.08596(18) -0.36772(9) 0.37547(4) 0.0383(3) Uani 1 1 d . . . 
O9 O 0.13678(14) -0.44525(8) 0.45683(4) 0.0245(2) Uani 1 1 d . . . 
C10 C 0.1022(2) -0.56994(12) 0.43599(6) 0.0261(3) Uani 1 1 d . . . 
H10A H 0.0244 -0.5654 0.4027 0.039 Uiso 1 1 calc R . . 
H10B H 0.0382 -0.6181 0.4600 0.039 Uiso 1 1 calc R . . 
H10C H 0.2214 -0.6087 0.4315 0.039 Uiso 1 1 calc R . . 
O11 O 0.11601(13) 0.09974(8) 0.40485(3) 0.0216(2) Uani 1 1 d . . . 
C12 C 0.0467(2) 0.09101(13) 0.34980(5) 0.0261(3) Uani 1 1 d . . . 
H12A H 0.0275 0.1730 0.3354 0.039 Uiso 1 1 calc R . . 
H12B H -0.0717 0.0465 0.3455 0.039 Uiso 1 1 calc R . . 
H12C H 0.1382 0.0477 0.3318 0.039 Uiso 1 1 calc R . . 
C13 C 0.26312(18) 0.12427(11) 0.50776(5) 0.0174(3) Uani 1 1 d . . . 
H13 H 0.2351 0.1951 0.4875 0.021 Uiso 1 1 calc R . . 
C14 C 0.33984(17) 0.13572(11) 0.55992(5) 0.0165(3) Uani 1 1 d . . . 
C15 C 0.38776(17) 0.02729(11) 0.59135(5) 0.0159(3) Uani 1 1 d . . . 
C16 C 0.35184(17) -0.09194(11) 0.56945(5) 0.0167(3) Uani 1 1 d . . . 
C17 C 0.4044(2) -0.20667(12) 0.60122(5) 0.0228(3) Uani 1 1 d . . . 
H17A H 0.4866 -0.1845 0.6324 0.034 Uiso 1 1 calc R . . 
H17B H 0.4692 -0.2638 0.5808 0.034 Uiso 1 1 calc R . . 
H17C H 0.2912 -0.2451 0.6108 0.034 Uiso 1 1 calc R . . 
C18 C 0.37419(18) 0.25509(11) 0.58417(5) 0.0180(3) Uani 1 1 d . . . 
C19 C 0.45159(18) 0.26137(11) 0.63540(5) 0.0197(3) Uani 1 1 d . . . 
H19 H 0.4720 0.3375 0.6523 0.024 Uiso 1 1 calc R . . 
C20 C 0.50019(17) 0.14826(11) 0.66216(5) 0.0173(3) Uani 1 1 d . . . 
N21 N 0.47105(15) 0.03605(9) 0.64281(4) 0.0171(2) Uani 1 1 d . . . 
O22 O 0.32486(14) 0.35309(8) 0.55265(4) 0.0237(2) Uani 1 1 d . . . 
C23 C 0.3716(2) 0.47435(12) 0.57390(6) 0.0263(3) Uani 1 1 d . . . 
H23A H 0.3299 0.5364 0.5482 0.039 Uiso 1 1 calc R . . 
H23B H 0.5068 0.4806 0.5831 0.039 Uiso 1 1 calc R . . 
H23C H 0.3092 0.4870 0.6047 0.039 Uiso 1 1 calc R . . 
C24 C 0.59670(18) 0.16191(12) 0.71757(5) 0.0199(3) Uani 1 1 d . . . 
O25 O 0.60061(16) 0.25863(9) 0.74139(4) 0.0324(3) Uani 1 1 d . . . 
O26 O 0.68003(13) 0.05764(8) 0.73622(3) 0.0232(2) Uani 1 1 d . . . 
C27 C 0.7736(2) 0.06438(14) 0.78957(5) 0.0300(3) Uani 1 1 d . . . 
H27A H 0.8728 0.1257 0.7916 0.045 Uiso 1 1 calc R . . 
H27B H 0.8276 -0.0152 0.7997 0.045 Uiso 1 1 calc R . . 
H27C H 0.6826 0.0871 0.8127 0.045 Uiso 1 1 calc R . . 
C28 C 0.6244(3) 0.15610(17) 0.24362(7) 0.0408(4) Uani 1 1 d . . . 
H28A H 0.719(3) 0.210(2) 0.2570(8) 0.061 Uiso 1 1 d . . . 
H28B H 0.553(3) 0.1402(18) 0.2733(9) 0.061 Uiso 1 1 d . . . 
H28C H 0.543(3) 0.194(2) 0.2179(9) 0.061 Uiso 1 1 d . . . 
C29 C 0.6913(2) 0.04012(17) 0.22420(7) 0.0375(4) Uani 1 1 d . . . 
N30 N 0.7406(2) -0.05194(16) 0.20848(7) 0.0580(5) Uani 1 1 d . . . 
 
 
_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 1.3152(16) . ? 
N1 C6 1.3815(16) . ? 
C2 C3 1.4222(17) . ? 
C2 C7 1.5082(17) . ? 
C3 C4 1.3622(18) . ? 
C4 O11 1.3491(15) . ? 
C4 C5 1.4350(17) . ? 
C5 C13 1.3893(18) . ? 
C5 C6 1.4352(17) . ? 
C6 C16 1.4127(18) . ? 
C7 O8 1.2043(16) . ? 
C7 O9 1.3290(15) . ? 
O9 C10 1.4536(15) . ? 
O11 C12 1.4402(15) . ? 
C13 C14 1.3866(17) . ? 
C14 C18 1.4347(17) . ? 
C14 C15 1.4350(17) . ? 
C15 N21 1.3815(16) . ? 
C15 C16 1.4108(17) . ? 
C16 C17 1.5006(17) . ? 
C18 O22 1.3483(15) . ? 
C18 C19 1.3622(18) . ? 
C19 C20 1.4186(17) . ? 
C20 N21 1.3119(15) . ? 
C20 C24 1.5072(17) . ? 
O22 C23 1.4368(15) . ? 
C24 O25 1.2052(15) . ? 
C24 O26 1.3289(15) . ? 
O26 C27 1.4477(15) . ? 
C28 C29 1.445(3) . ? 
C29 N30 1.140(2) . ? 
 
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 116.70(11) . . ? 
N1 C2 C3 126.28(12) . . ? 
N1 C2 C7 118.46(11) . . ? 
C3 C2 C7 115.25(11) . . ? 
C4 C3 C2 117.84(11) . . ? 
O11 C4 C3 125.99(11) . . ? 
O11 C4 C5 114.73(11) . . ? 
C3 C4 C5 119.27(11) . . ? 
C13 C5 C4 121.69(11) . . ? 
C13 C5 C6 120.18(11) . . ? 
C4 C5 C6 118.13(11) . . ? 
N1 C6 C16 118.26(11) . . ? 
N1 C6 C5 121.75(11) . . ? 
C16 C6 C5 119.99(11) . . ? 
O8 C7 O9 123.81(12) . . ? 
O8 C7 C2 122.38(12) . . ? 
O9 C7 C2 113.80(11) . . ? 
C7 O9 C10 116.60(10) . . ? 
C4 O11 C12 117.46(10) . . ? 
C14 C13 C5 120.34(11) . . ? 
C13 C14 C18 121.57(11) . . ? 
C13 C14 C15 120.52(11) . . ? 
C18 C14 C15 117.91(11) . . ? 
N21 C15 C16 118.53(11) . . ? 
N21 C15 C14 121.69(11) . . ? 
C16 C15 C14 119.77(11) . . ? 
C15 C16 C6 119.16(11) . . ? 
C15 C16 C17 120.72(11) . . ? 
C6 C16 C17 120.11(11) . . ? 
O22 C18 C19 125.72(11) . . ? 
O22 C18 C14 114.96(11) . . ? 
C19 C18 C14 119.31(11) . . ? 
C18 C19 C20 118.00(11) . . ? 
N21 C20 C19 126.05(11) . . ? 
N21 C20 C24 118.60(11) . . ? 
C19 C20 C24 115.35(11) . . ? 
C20 N21 C15 116.96(10) . . ? 
C18 O22 C23 116.85(10) . . ? 
O25 C24 O26 124.38(12) . . ? 
O25 C24 C20 122.80(12) . . ? 
O26 C24 C20 112.79(10) . . ? 
C24 O26 C27 115.46(10) . . ? 
N30 C29 C28 178.7(2) . . ? 
 
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 C3 -0.16(18) . . . . ? 
C6 N1 C2 C7 178.80(10) . . . . ? 
N1 C2 C3 C4 -1.3(2) . . . . ? 
C7 C2 C3 C4 179.71(11) . . . . ? 
C2 C3 C4 O11 -179.01(11) . . . . ? 
C2 C3 C4 C5 1.24(18) . . . . ? 
O11 C4 C5 C13 -0.05(18) . . . . ? 
C3 C4 C5 C13 179.74(11) . . . . ? 
O11 C4 C5 C6 -179.68(10) . . . . ? 
C3 C4 C5 C6 0.10(18) . . . . ? 
C2 N1 C6 C16 -177.83(11) . . . . ? 
C2 N1 C6 C5 1.62(17) . . . . ? 
C13 C5 C6 N1 178.75(11) . . . . ? 
C4 C5 C6 N1 -1.61(18) . . . . ? 
C13 C5 C6 C16 -1.81(18) . . . . ? 
C4 C5 C6 C16 177.83(11) . . . . ? 
N1 C2 C7 O8 -168.90(12) . . . . ? 
C3 C2 C7 O8 10.16(19) . . . . ? 
N1 C2 C7 O9 10.80(17) . . . . ? 
C3 C2 C7 O9 -170.13(11) . . . . ? 
O8 C7 O9 C10 -0.01(19) . . . . ? 
C2 C7 O9 C10 -179.71(11) . . . . ? 
C3 C4 O11 C12 -2.58(18) . . . . ? 
C5 C4 O11 C12 177.19(10) . . . . ? 
C4 C5 C13 C14 -179.25(11) . . . . ? 
C6 C5 C13 C14 0.37(19) . . . . ? 
C5 C13 C14 C18 -178.72(11) . . . . ? 
C5 C13 C14 C15 1.38(19) . . . . ? 
C13 C14 C15 N21 177.49(11) . . . . ? 
C18 C14 C15 N21 -2.41(18) . . . . ? 
C13 C14 C15 C16 -1.71(18) . . . . ? 
C18 C14 C15 C16 178.39(11) . . . . ? 
N21 C15 C16 C6 -178.96(10) . . . . ? 
C14 C15 C16 C6 0.26(18) . . . . ? 
N21 C15 C16 C17 -0.50(18) . . . . ? 
C14 C15 C16 C17 178.73(11) . . . . ? 
N1 C6 C16 C15 -179.08(11) . . . . ? 
C5 C6 C16 C15 1.46(18) . . . . ? 
N1 C6 C16 C17 2.44(18) . . . . ? 
C5 C6 C16 C17 -177.01(11) . . . . ? 
C13 C14 C18 O22 0.56(18) . . . . ? 
C15 C14 C18 O22 -179.54(10) . . . . ? 
C13 C14 C18 C19 -179.35(11) . . . . ? 
C15 C14 C18 C19 0.55(18) . . . . ? 
O22 C18 C19 C20 -178.07(11) . . . . ? 
C14 C18 C19 C20 1.82(18) . . . . ? 
C18 C19 C20 N21 -2.8(2) . . . . ? 
C18 C19 C20 C24 176.22(11) . . . . ? 
C19 C20 N21 C15 0.98(19) . . . . ? 
C24 C20 N21 C15 -177.99(10) . . . . ? 
C16 C15 N21 C20 -179.13(11) . . . . ? 
C14 C15 N21 C20 1.66(17) . . . . ? 
C19 C18 O22 C23 5.04(19) . . . . ? 
C14 C18 O22 C23 -174.85(11) . . . . ? 
N21 C20 C24 O25 -167.21(12) . . . . ? 
C19 C20 C24 O25 13.71(19) . . . . ? 
N21 C20 C24 O26 14.54(17) . . . . ? 
C19 C20 C24 O26 -164.54(11) . . . . ? 
O25 C24 O26 C27 2.42(19) . . . . ? 
C20 C24 O26 C27 -179.36(11) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.992 
_diffrn_reflns_theta_full              26.37 
_diffrn_measured_fraction_theta_full   0.992 
_refine_diff_density_max    0.275 
_refine_diff_density_min   -0.215 
_refine_diff_density_rms    0.045 
