# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 N7 O8 Zn2' _chemical_formula_weight 598.10 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P43212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+1/4' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.8140(13) _cell_length_b 10.8140(13) _cell_length_c 25.410(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2971.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8240 _cell_measurement_theta_min 3.0550 _cell_measurement_theta_max 27.4934 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.662 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6355 _exptl_absorpt_correction_T_max 0.7217 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _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 Mercury _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22870 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3397 _reflns_number_gt 3322 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2000)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The Flack parameter of 0.27 in the structural analysis suggests that the crystal may be racemic twinning. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+1.6083P] 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 constr _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 0.276(18) _refine_ls_number_reflns 3397 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.124 525 39 ' ' 2 0.500 1.000 0.644 525 39 ' ' _platon_squeeze_details ; ; 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 Zn1 Zn 0.54341(3) 0.54094(3) 0.079250(8) 0.02677(9) Uani 1 1 d . . . O1 O 0.4628(2) 0.40525(19) 0.04012(8) 0.0482(5) Uani 1 1 d . . . O2 O 0.1993(2) 0.0972(2) 0.13779(7) 0.0437(3) Uani 1 1 d . . . O3 O 0.0336(2) 0.0330(2) 0.09791(7) 0.0437(3) Uani 1 1 d . . . O4 O -0.1818(6) 0.1796(7) 0.05811(19) 0.207(4) Uani 1 1 d . . . H4A H -0.2162 0.2411 0.0729 0.248 Uiso 1 1 d R . . H4B H -0.1210 0.1383 0.0700 0.248 Uiso 1 1 d R . . N1 N 0.8886(2) 0.8426(2) 0.15828(8) 0.0377(5) Uani 1 1 d . . . N2 N 0.6881(3) 0.6931(3) 0.13179(9) 0.0457(6) Uani 1 1 d . . . N3 N 0.6427(2) 0.6396(2) 0.02663(7) 0.0283(4) Uani 1 1 d . . . N4 N 0.78039(19) 0.78039(19) 0.0000 0.0419(7) Uani 1 2 d S . . C1 C 0.7171(4) 0.7166(4) 0.18163(11) 0.0593(9) Uani 1 1 d . . . H1 H 0.6680 0.6840 0.2083 0.071 Uiso 1 1 calc R . . C2 C 0.8188(3) 0.7888(3) 0.19499(11) 0.0521(9) Uani 1 1 d . . . H2 H 0.8386 0.7997 0.2303 0.063 Uiso 1 1 calc R . . C3 C 0.8591(3) 0.8206(3) 0.10840(10) 0.0389(7) Uani 1 1 d . . . H3 H 0.9066 0.8553 0.0817 0.047 Uiso 1 1 calc R . . C4 C 0.7584(3) 0.7466(3) 0.09534(10) 0.0361(5) Uani 1 1 d . . . C5 C 0.7282(3) 0.7224(3) 0.04066(10) 0.0342(5) Uani 1 1 d . . . C7 C 0.3962(2) 0.3962(2) 0.0000 0.0312(6) Uani 1 2 d S . . C8 C 0.2983(2) 0.2983(2) 0.0000 0.0295(6) Uani 1 2 d S . . C9 C 0.2648(3) 0.2414(3) 0.04669(9) 0.0331(6) Uani 1 1 d . . . H9 H 0.3042 0.2631 0.0779 0.040 Uiso 1 1 calc R . . C10 C 0.1727(2) 0.1520(2) 0.04707(9) 0.0312(5) Uani 1 1 d . . . C11 C 0.1168(2) 0.1168(2) 0.0000 0.0312(6) Uani 1 2 d S . . H11 H 0.0560 0.0560 0.0000 0.037 Uiso 1 2 calc SR . . C12 C 0.1336(3) 0.0922(2) 0.09768(10) 0.0344(6) Uani 1 1 d . . . 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 Zn1 0.03029(15) 0.03234(15) 0.01767(13) 0.00220(10) 0.00306(10) -0.00104(10) O1 0.0564(12) 0.0442(11) 0.0442(11) 0.0036(9) -0.0171(10) -0.0214(10) O2 0.0489(8) 0.0536(9) 0.0285(6) 0.0097(6) 0.0028(6) -0.0100(6) O3 0.0489(8) 0.0536(9) 0.0285(6) 0.0097(6) 0.0028(6) -0.0100(6) O4 0.219(7) 0.293(9) 0.108(3) -0.034(5) -0.035(4) 0.140(6) N1 0.0408(12) 0.0454(13) 0.0270(10) 0.0030(9) -0.0039(9) -0.0122(11) N2 0.0528(15) 0.0503(15) 0.0341(11) 0.0064(11) -0.0033(11) -0.0216(11) N3 0.0314(11) 0.0311(11) 0.0223(9) 0.0000(8) -0.0009(8) -0.0067(7) N4 0.0490(12) 0.0490(12) 0.0277(14) 0.0039(13) -0.0039(13) -0.0225(15) C1 0.071(2) 0.076(3) 0.0311(13) 0.0075(16) 0.0026(16) -0.0333(18) C2 0.064(2) 0.068(2) 0.0243(11) 0.0064(13) -0.0048(13) -0.0243(17) C3 0.0436(15) 0.0464(15) 0.0267(11) 0.0033(10) -0.0025(10) -0.0178(13) C4 0.0397(14) 0.0398(14) 0.0289(11) 0.0050(11) -0.0047(11) -0.0131(11) C5 0.0347(13) 0.0390(14) 0.0289(11) -0.0004(11) -0.0024(11) -0.0117(10) C7 0.0311(10) 0.0311(10) 0.0314(15) -0.0012(11) 0.0012(11) -0.0053(13) C8 0.0315(10) 0.0315(10) 0.0254(14) -0.0028(11) 0.0028(11) -0.0093(12) C9 0.0370(13) 0.0383(14) 0.0239(11) -0.0013(10) -0.0020(10) -0.0098(11) C10 0.0366(13) 0.0351(13) 0.0220(10) 0.0045(9) 0.0012(9) -0.0066(10) C11 0.0352(10) 0.0352(10) 0.0233(14) 0.0007(11) -0.0007(11) -0.0109(13) C12 0.0407(14) 0.0367(13) 0.0259(11) 0.0041(9) 0.0049(10) -0.0045(11) _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 Zn1 O1 1.9754(19) . ? Zn1 O3 2.0190(18) 5 ? Zn1 N3 2.0193(18) . ? Zn1 N1 2.119(2) 5_465 ? Zn1 O2 2.403(2) 5 ? Zn1 C12 2.544(2) 5 ? O1 C7 1.252(2) . ? O2 C12 1.244(3) . ? O2 Zn1 2.403(2) 5_455 ? O3 C12 1.256(3) . ? O3 Zn1 2.0190(18) 5_455 ? O4 H4A 0.8496 . ? O4 H4B 0.8498 . ? N1 C3 1.328(3) . ? N1 C2 1.334(4) . ? N1 Zn1 2.119(2) 5_565 ? N2 C1 1.329(4) . ? N2 C4 1.331(3) . ? N3 C5 1.336(3) . ? N3 N3 1.354(3) 7 ? N4 C5 1.334(3) 7 ? N4 C5 1.334(3) . ? C1 C2 1.391(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.391(3) . ? C3 H3 0.9300 . ? C4 C5 1.451(3) . ? C7 O1 1.252(2) 7 ? C7 C8 1.497(4) . ? C8 C9 1.385(3) 7 ? C8 C9 1.385(3) . ? C9 C10 1.388(3) . ? C9 H9 0.9300 . ? C10 C11 1.394(3) . ? C10 C12 1.500(3) . ? C11 C10 1.394(3) 7 ? C11 H11 0.9300 . ? C12 Zn1 2.544(2) 5_455 ? 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 O1 Zn1 O3 98.28(9) . 5 ? O1 Zn1 N3 107.09(8) . . ? O3 Zn1 N3 147.57(9) 5 . ? O1 Zn1 N1 99.67(10) . 5_465 ? O3 Zn1 N1 93.26(8) 5 5_465 ? N3 Zn1 N1 101.85(9) . 5_465 ? O1 Zn1 O2 91.33(8) . 5 ? O3 Zn1 O2 58.06(7) 5 5 ? N3 Zn1 O2 100.73(9) . 5 ? N1 Zn1 O2 150.65(8) 5_465 5 ? O1 Zn1 C12 96.67(9) . 5 ? O3 Zn1 C12 29.16(8) 5 5 ? N3 Zn1 C12 125.34(9) . 5 ? N1 Zn1 C12 122.01(8) 5_465 5 ? O2 Zn1 C12 28.94(8) 5 5 ? C7 O1 Zn1 136.20(18) . . ? C12 O2 Zn1 81.82(16) . 5_455 ? C12 O3 Zn1 99.27(16) . 5_455 ? H4A O4 H4B 126.4 . . ? C3 N1 C2 117.0(2) . . ? C3 N1 Zn1 116.03(17) . 5_565 ? C2 N1 Zn1 127.01(19) . 5_565 ? C1 N2 C4 116.4(2) . . ? C5 N3 N3 105.49(13) . 7 ? C5 N3 Zn1 123.06(16) . . ? N3 N3 Zn1 131.42(5) 7 . ? C5 N4 C5 101.7(3) 7 . ? N2 C1 C2 121.8(3) . . ? N2 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? N1 C2 C1 121.4(3) . . ? N1 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? N1 C3 C4 121.2(2) . . ? N1 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? N2 C4 C3 122.1(2) . . ? N2 C4 C5 117.3(2) . . ? C3 C4 C5 120.6(2) . . ? N4 C5 N3 113.7(2) . . ? N4 C5 C4 124.2(2) . . ? N3 C5 C4 122.2(2) . . ? O1 C7 O1 125.0(3) . 7 ? O1 C7 C8 117.51(16) . . ? O1 C7 C8 117.51(16) 7 . ? C9 C8 C9 120.1(3) 7 . ? C9 C8 C7 119.94(15) 7 . ? C9 C8 C7 119.94(15) . . ? C8 C9 C10 120.2(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 119.7(2) . . ? C9 C10 C12 120.6(2) . . ? C11 C10 C12 119.7(2) . . ? C10 C11 C10 120.0(3) . 7 ? C10 C11 H11 120.0 . . ? C10 C11 H11 120.0 7 . ? O2 C12 O3 120.7(2) . . ? O2 C12 C10 121.5(2) . . ? O3 C12 C10 117.8(2) . . ? O2 C12 Zn1 69.24(14) . 5_455 ? O3 C12 Zn1 51.57(12) . 5_455 ? C10 C12 Zn1 167.88(19) . 5_455 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.771 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 926786' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H27 Cd2 N9 O9' _chemical_formula_weight 846.38 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 20.730(8) _cell_length_b 14.751(5) _cell_length_c 20.709(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.174(4) _cell_angle_gamma 90.00 _cell_volume 6283(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7141 _cell_measurement_theta_min 2.5152 _cell_measurement_theta_max 27.4778 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3360 _exptl_absorpt_coefficient_mu 1.421 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6918 _exptl_absorpt_correction_T_max 0.8046 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _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 Mercury _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18081 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5836 _reflns_number_gt 4736 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2000)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+45.8723P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5836 _refine_ls_number_parameters 432 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.2053 _refine_ls_wR_factor_gt 0.1886 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.002 _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 Cd1 Cd 0.43240(2) 0.49859(3) 0.17921(2) 0.0173(6) Uani 1 1 d . . . Cd2 Cd 0.45381(2) 0.00001(3) 0.10118(2) 0.0185(6) Uani 1 1 d . . . C8 C 0.4730(3) 0.3116(4) 0.1293(3) 0.0213(15) Uani 1 1 d . . . H8 H 0.4910 0.3541 0.1036 0.026 Uiso 1 1 calc R . . N7 N 0.4465(3) 0.3394(4) 0.1814(3) 0.0193(13) Uani 1 1 d . . . C10 C 0.4264(3) 0.1851(4) 0.2032(3) 0.0213(15) Uani 1 1 d . . . H10 H 0.4106 0.1424 0.2303 0.026 Uiso 1 1 calc R . . N6 N 0.4515(3) 0.1562(4) 0.1506(3) 0.0244(14) Uani 1 1 d . . . C9 C 0.4230(3) 0.2745(5) 0.2189(3) 0.0255(16) Uani 1 1 d . . . H9 H 0.4043 0.2914 0.2556 0.031 Uiso 1 1 calc R . . C7 C 0.4742(3) 0.2202(4) 0.1126(3) 0.0221(15) Uani 1 1 d . . . N5 N 0.4992(3) 0.1052(3) 0.0352(3) 0.0204(13) Uani 1 1 d . . . C6 C 0.4964(3) 0.1919(4) 0.0528(3) 0.0191(15) Uani 1 1 d U . . N3 N 0.5135(3) 0.2513(4) 0.0083(3) 0.0263(15) Uani 1 1 d . . . C12 C 0.2897(4) 0.5123(4) 0.3535(3) 0.0210(15) Uani 1 1 d . . . H12 H 0.2691 0.5109 0.3110 0.025 Uiso 1 1 calc R . . O1 O 0.3621(3) 0.4985(4) 0.2525(3) 0.0402(17) Uani 1 1 d . . . C17 C 0.3959(4) 0.5063(4) 0.3068(3) 0.0209(16) Uani 1 1 d . . . C11 C 0.3582(3) 0.5115(4) 0.3653(4) 0.0212(16) Uani 1 1 d . . . N4 N 0.5173(3) 0.1061(4) -0.0255(3) 0.0207(13) Uani 1 1 d . . . C1 C 0.5459(3) 0.3128(5) -0.1181(4) 0.0242(16) Uani 1 1 d . . . H1 H 0.5331 0.3551 -0.0888 0.029 Uiso 1 1 calc R . . C4 C 0.5452(3) 0.2223(5) -0.1020(3) 0.0224(16) Uani 1 1 d . . . C5 C 0.5261(4) 0.1938(4) -0.0393(3) 0.0248(16) Uani 1 1 d . . . O2 O 0.4556(3) 0.5089(3) 0.3141(3) 0.0341(15) Uani 1 1 d . . . C18 C 0.1795(4) 0.5116(4) 0.3937(4) 0.0238(16) Uani 1 1 d . . . C15 C 0.3522(3) 0.5150(4) 0.4808(3) 0.0221(16) Uani 1 1 d . . . C16 C 0.3891(3) 0.5126(4) 0.4286(3) 0.0201(15) Uani 1 1 d . . . H16 H 0.4342 0.5117 0.4364 0.024 Uiso 1 1 calc R . . C14 C 0.2841(3) 0.5164(5) 0.4684(3) 0.0233(16) Uani 1 1 d . . . H14 H 0.2596 0.5183 0.5030 0.028 Uiso 1 1 calc R . . N1 N 0.5639(3) 0.3420(4) -0.1730(3) 0.0232(14) Uani 1 1 d . . . C13 C 0.2530(3) 0.5152(4) 0.4049(4) 0.0211(16) Uani 1 1 d . . . N2 N 0.5601(3) 0.1574(4) -0.1425(3) 0.0233(14) Uani 1 1 d . . . C2 C 0.5792(4) 0.2766(5) -0.2144(4) 0.0295(17) Uani 1 1 d . . . H2 H 0.5913 0.2935 -0.2544 0.035 Uiso 1 1 calc R . . C3 C 0.5773(4) 0.1860(5) -0.1992(4) 0.0301(17) Uani 1 1 d . . . H3 H 0.5884 0.1435 -0.2291 0.036 Uiso 1 1 calc R . . O6 O 0.4441(2) 0.5062(3) 0.5633(2) 0.0217(12) Uani 1 1 d . . . O3 O 0.1514(3) 0.5042(3) 0.3366(3) 0.0292(14) Uani 1 1 d . . . O4 O 0.1496(3) 0.5162(4) 0.4428(3) 0.0337(14) Uani 1 1 d . . . C19 C 0.3841(3) 0.5126(4) 0.5504(3) 0.0202(15) Uani 1 1 d . . . O8 O 0.5479(3) -0.0136(3) 0.1719(3) 0.0340(14) Uani 1 1 d . . . O5 O 0.3469(3) 0.5171(4) 0.5952(2) 0.0300(13) Uani 1 1 d . . . N8 N 0.2036(4) 0.3051(5) 0.6130(4) 0.049(2) Uani 1 1 d . . . O7 O 0.1207(3) 0.3597(4) 0.6617(3) 0.0422(15) Uani 1 1 d . . . C21 C 0.1741(4) 0.3706(6) 0.6448(4) 0.044(2) Uani 1 1 d . . . C20 C 0.2120(6) 0.4586(9) 0.6601(7) 0.085(4) Uani 1 1 d . . . H20A H 0.1901 0.4949 0.6891 0.128 Uiso 1 1 calc R . . H20B H 0.2146 0.4914 0.6206 0.128 Uiso 1 1 calc R . . H20C H 0.2550 0.4445 0.6804 0.128 Uiso 1 1 calc R . . C22 C 0.1676(6) 0.2222(7) 0.5964(7) 0.089(4) Uani 1 1 d . . . H22A H 0.1373 0.2120 0.6271 0.133 Uiso 1 1 calc R . . H22B H 0.1973 0.1721 0.5975 0.133 Uiso 1 1 calc R . . H22C H 0.1444 0.2276 0.5535 0.133 Uiso 1 1 calc R . . O9 O 0.6213(3) -0.1692(4) 0.1603(3) 0.0537(18) Uani 1 1 d . . . C23 C 0.2682(5) 0.3147(7) 0.5885(6) 0.070(3) Uani 1 1 d . . . H23A H 0.2873 0.3719 0.6023 0.105 Uiso 1 1 calc R . . H23B H 0.2624 0.3120 0.5418 0.105 Uiso 1 1 calc R . . H23C H 0.2964 0.2664 0.6055 0.105 Uiso 1 1 calc R . . N9 N 0.7206(5) -0.2114(7) 0.1419(9) 0.127(6) Uani 1 1 d . . . C25 C 0.6659(6) -0.1896(8) 0.1306(6) 0.094(5) Uani 1 1 d D . . C24 C 0.6479(6) -0.2017(12) 0.0505(6) 0.103(5) Uani 1 1 d D . . H24A H 0.6731 -0.1598 0.0286 0.155 Uiso 1 1 calc R . . H24B H 0.6025 -0.1900 0.0383 0.155 Uiso 1 1 calc R . . H24C H 0.6577 -0.2625 0.0383 0.155 Uiso 1 1 calc R . . C26 C 0.7427(7) -0.1969(13) 0.2186(6) 0.122(6) Uani 1 1 d . . . H26A H 0.7803 -0.1583 0.2247 0.183 Uiso 1 1 calc R . . H26B H 0.7531 -0.2545 0.2389 0.183 Uiso 1 1 calc R . . H26C H 0.7079 -0.1692 0.2381 0.183 Uiso 1 1 calc R . . C27 C 0.7734(4) -0.2296(8) 0.1040(5) 0.066(3) Uani 1 1 d . . . H27A H 0.7562 -0.2540 0.0624 0.099 Uiso 1 1 calc R . . H27B H 0.8027 -0.2727 0.1267 0.099 Uiso 1 1 calc R . . H27C H 0.7963 -0.1744 0.0979 0.099 Uiso 1 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 Cd1 0.0196(7) 0.0207(7) 0.0120(7) -0.00013(17) 0.0039(2) 0.00080(17) Cd2 0.0193(7) 0.0189(7) 0.0178(7) 0.00000(17) 0.0040(2) -0.00006(17) C8 0.023(4) 0.022(3) 0.021(4) -0.001(3) 0.008(3) 0.000(3) N7 0.018(3) 0.028(3) 0.013(3) -0.005(2) 0.004(2) 0.003(2) C10 0.027(4) 0.026(3) 0.012(3) 0.004(3) 0.004(3) -0.007(3) N6 0.029(3) 0.021(3) 0.023(3) 0.001(2) 0.002(2) 0.001(2) C9 0.033(4) 0.031(4) 0.015(3) 0.010(3) 0.010(3) -0.002(3) C7 0.020(3) 0.020(3) 0.026(4) 0.001(3) 0.004(3) -0.002(3) N5 0.022(3) 0.017(3) 0.024(3) 0.000(2) 0.008(2) -0.001(2) C6 0.026(3) 0.020(3) 0.014(3) 0.007(2) 0.012(2) 0.002(2) N3 0.046(4) 0.021(3) 0.014(3) -0.004(2) 0.017(3) -0.005(3) C12 0.027(4) 0.023(4) 0.012(3) 0.002(2) 0.002(3) -0.001(3) O1 0.027(3) 0.080(5) 0.014(3) -0.009(2) 0.005(2) -0.002(2) C17 0.024(4) 0.021(4) 0.018(4) 0.005(3) 0.005(3) 0.009(3) C11 0.017(3) 0.025(4) 0.023(4) -0.001(3) 0.005(3) -0.003(2) N4 0.021(3) 0.022(3) 0.018(3) 0.001(2) 0.003(2) -0.002(2) C1 0.024(4) 0.029(4) 0.022(4) -0.004(3) 0.014(3) -0.001(3) C4 0.022(4) 0.029(4) 0.019(4) -0.003(3) 0.013(3) -0.003(3) C5 0.037(4) 0.020(3) 0.018(4) 0.000(3) 0.006(3) 0.000(3) O2 0.023(3) 0.060(4) 0.020(3) -0.003(2) 0.004(2) 0.001(2) C18 0.024(4) 0.025(4) 0.022(4) -0.004(3) 0.002(3) 0.002(3) C15 0.023(4) 0.033(4) 0.011(3) -0.007(3) 0.003(3) 0.002(3) C16 0.015(3) 0.025(3) 0.022(4) -0.004(3) 0.007(3) 0.003(2) C14 0.015(3) 0.038(4) 0.018(4) 0.001(3) 0.009(3) 0.001(3) N1 0.032(3) 0.019(3) 0.019(3) -0.005(2) 0.003(2) -0.001(2) C13 0.015(3) 0.026(3) 0.023(4) -0.005(3) 0.006(3) 0.003(3) N2 0.028(3) 0.027(3) 0.017(3) -0.008(2) 0.011(2) -0.001(2) C2 0.041(4) 0.027(4) 0.021(4) 0.003(3) 0.006(3) 0.002(3) C3 0.035(4) 0.034(4) 0.023(4) 0.000(3) 0.010(3) -0.006(3) O6 0.021(3) 0.026(3) 0.018(3) -0.0004(18) 0.003(2) 0.0018(18) O3 0.023(3) 0.040(3) 0.024(3) 0.004(2) 0.000(2) 0.000(2) O4 0.022(3) 0.058(3) 0.022(3) -0.001(2) 0.011(2) 0.001(2) C19 0.026(4) 0.015(3) 0.020(4) -0.002(2) 0.007(3) 0.000(2) O8 0.029(3) 0.043(3) 0.028(3) 0.007(2) -0.003(2) 0.004(2) O5 0.027(3) 0.053(3) 0.012(3) -0.003(2) 0.006(2) -0.001(2) N8 0.040(4) 0.054(5) 0.056(5) 0.006(4) 0.016(4) 0.001(3) O7 0.033(3) 0.057(4) 0.042(3) 0.006(3) 0.023(3) 0.002(3) C21 0.045(5) 0.055(5) 0.033(5) 0.004(4) 0.012(4) 0.006(4) C20 0.065(7) 0.093(9) 0.105(10) -0.052(8) 0.040(7) -0.027(7) C22 0.077(8) 0.039(6) 0.154(14) -0.014(7) 0.028(8) -0.006(5) O9 0.053(4) 0.056(4) 0.056(4) 0.005(3) 0.022(3) 0.019(3) C23 0.074(8) 0.062(7) 0.080(8) -0.015(6) 0.035(6) -0.012(6) N9 0.055(7) 0.067(7) 0.27(2) -0.012(9) 0.084(9) 0.003(5) C25 0.070(9) 0.058(7) 0.161(15) 0.039(8) 0.046(9) 0.008(6) C24 0.061(8) 0.179(15) 0.065(9) -0.003(9) -0.008(6) 0.000(9) C26 0.112(12) 0.225(19) 0.025(6) 0.003(9) -0.010(7) -0.024(12) C27 0.033(5) 0.101(9) 0.063(7) -0.023(6) -0.002(5) 0.006(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 Cd1 O1 2.231(5) . ? Cd1 O2 2.313(5) 2_655 ? Cd1 O5 2.335(5) 6_565 ? Cd1 N1 2.357(5) 5_665 ? Cd1 N7 2.366(5) . ? Cd1 O6 2.443(5) 6_565 ? Cd1 C19 2.734(7) 6_565 ? Cd2 O4 2.234(5) 4_545 ? Cd2 O8 2.297(6) . ? Cd2 N5 2.341(5) . ? Cd2 N4 2.346(5) 5_655 ? Cd2 N2 2.504(6) 5_655 ? Cd2 N6 2.524(6) . ? C8 N7 1.334(8) . ? C8 C7 1.394(9) . ? C8 H8 0.9300 . ? N7 C9 1.360(8) . ? C10 N6 1.333(9) . ? C10 C9 1.363(10) . ? C10 H10 0.9300 . ? N6 C7 1.351(9) . ? C9 H9 0.9300 . ? C7 C6 1.437(9) . ? N5 C6 1.332(8) . ? N5 N4 1.356(8) . ? C6 N3 1.352(8) . ? N3 C5 1.350(9) . ? C12 C13 1.385(10) . ? C12 C11 1.409(10) . ? C12 H12 0.9300 . ? O1 C17 1.253(9) . ? C17 O2 1.229(9) . ? C17 C11 1.523(9) . ? C11 C16 1.386(10) . ? N4 C5 1.343(8) . ? N4 Cd2 2.346(5) 5_655 ? C1 N1 1.314(9) . ? C1 C4 1.377(10) . ? C1 H1 0.9300 . ? C4 N2 1.334(8) . ? C4 C5 1.464(9) . ? O2 Cd1 2.313(5) 2_655 ? C18 O3 1.255(9) . ? C18 O4 1.258(9) . ? C18 C13 1.514(10) . ? C15 C16 1.400(9) . ? C15 C14 1.403(10) . ? C15 C19 1.509(10) . ? C16 H16 0.9300 . ? C14 C13 1.391(10) . ? C14 H14 0.9300 . ? N1 C2 1.353(9) . ? N1 Cd1 2.357(5) 5_665 ? N2 C3 1.338(9) . ? N2 Cd2 2.504(6) 5_655 ? C2 C3 1.374(10) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? O6 C19 1.243(9) . ? O6 Cd1 2.443(5) 6_566 ? O4 Cd2 2.234(5) 4 ? C19 O5 1.280(8) . ? C19 Cd1 2.734(7) 6_566 ? O5 Cd1 2.335(5) 6_566 ? N8 C21 1.358(12) . ? N8 C22 1.451(13) . ? N8 C23 1.498(12) . ? O7 C21 1.212(10) . ? C21 C20 1.529(14) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O9 C25 1.211(13) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? N9 C25 1.174(16) . ? N9 C27 1.449(13) . ? N9 C26 1.613(19) . ? C25 C24 1.664(9) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 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 O1 Cd1 O2 134.0(2) . 2_655 ? O1 Cd1 O5 90.4(2) . 6_565 ? O2 Cd1 O5 135.54(18) 2_655 6_565 ? O1 Cd1 N1 93.8(2) . 5_665 ? O2 Cd1 N1 84.17(19) 2_655 5_665 ? O5 Cd1 N1 94.87(19) 6_565 5_665 ? O1 Cd1 N7 94.38(19) . . ? O2 Cd1 N7 86.75(18) 2_655 . ? O5 Cd1 N7 89.80(18) 6_565 . ? N1 Cd1 N7 170.6(2) 5_665 . ? O1 Cd1 O6 145.27(19) . 6_565 ? O2 Cd1 O6 80.68(18) 2_655 6_565 ? O5 Cd1 O6 54.89(17) 6_565 6_565 ? N1 Cd1 O6 88.15(16) 5_665 6_565 ? N7 Cd1 O6 87.85(16) . 6_565 ? O1 Cd1 C19 118.2(2) . 6_565 ? O2 Cd1 C19 107.7(2) 2_655 6_565 ? O5 Cd1 C19 27.85(19) 6_565 6_565 ? N1 Cd1 C19 90.99(18) 5_665 6_565 ? N7 Cd1 C19 89.33(17) . 6_565 ? O6 Cd1 C19 27.05(19) 6_565 6_565 ? O4 Cd2 O8 164.6(2) 4_545 . ? O4 Cd2 N5 97.26(19) 4_545 . ? O8 Cd2 N5 93.37(19) . . ? O4 Cd2 N4 96.36(19) 4_545 5_655 ? O8 Cd2 N4 95.77(19) . 5_655 ? N5 Cd2 N4 84.11(19) . 5_655 ? O4 Cd2 N2 95.34(19) 4_545 5_655 ? O8 Cd2 N2 79.97(18) . 5_655 ? N5 Cd2 N2 152.37(17) . 5_655 ? N4 Cd2 N2 70.09(18) 5_655 5_655 ? O4 Cd2 N6 90.09(19) 4_545 . ? O8 Cd2 N6 83.06(18) . . ? N5 Cd2 N6 70.20(19) . . ? N4 Cd2 N6 154.12(18) 5_655 . ? N2 Cd2 N6 134.34(19) 5_655 . ? N7 C8 C7 121.3(6) . . ? N7 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 N7 C9 117.2(6) . . ? C8 N7 Cd1 110.6(4) . . ? C9 N7 Cd1 131.1(4) . . ? N6 C10 C9 122.8(6) . . ? N6 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? C10 N6 C7 116.9(6) . . ? C10 N6 Cd2 130.7(4) . . ? C7 N6 Cd2 112.1(4) . . ? N7 C9 C10 120.8(6) . . ? N7 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? N6 C7 C8 120.9(6) . . ? N6 C7 C6 118.2(6) . . ? C8 C7 C6 120.8(6) . . ? C6 N5 N4 105.7(5) . . ? C6 N5 Cd2 116.3(4) . . ? N4 N5 Cd2 136.5(4) . . ? N5 C6 N3 114.4(6) . . ? N5 C6 C7 122.9(5) . . ? N3 C6 C7 122.7(6) . . ? C5 N3 C6 100.4(6) . . ? C13 C12 C11 120.3(7) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C17 O1 Cd1 105.8(5) . . ? O2 C17 O1 123.7(7) . . ? O2 C17 C11 120.6(6) . . ? O1 C17 C11 115.7(6) . . ? C16 C11 C12 120.0(6) . . ? C16 C11 C17 122.1(6) . . ? C12 C11 C17 117.9(6) . . ? C5 N4 N5 105.6(5) . . ? C5 N4 Cd2 116.5(4) . 5_655 ? N5 N4 Cd2 137.4(4) . 5_655 ? N1 C1 C4 122.7(6) . . ? N1 C1 H1 118.7 . . ? C4 C1 H1 118.7 . . ? N2 C4 C1 122.2(6) . . ? N2 C4 C5 117.5(6) . . ? C1 C4 C5 120.3(6) . . ? N4 C5 N3 113.9(6) . . ? N4 C5 C4 121.7(6) . . ? N3 C5 C4 124.4(6) . . ? C17 O2 Cd1 173.3(5) . 2_655 ? O3 C18 O4 123.3(7) . . ? O3 C18 C13 119.2(7) . . ? O4 C18 C13 117.5(7) . . ? C16 C15 C14 119.5(6) . . ? C16 C15 C19 121.4(6) . . ? C14 C15 C19 119.0(6) . . ? C11 C16 C15 120.0(6) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C13 C14 C15 120.7(6) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C1 N1 C2 115.5(6) . . ? C1 N1 Cd1 112.8(4) . 5_665 ? C2 N1 Cd1 131.6(5) . 5_665 ? C12 C13 C14 119.5(7) . . ? C12 C13 C18 121.3(7) . . ? C14 C13 C18 119.1(6) . . ? C4 N2 C3 115.8(6) . . ? C4 N2 Cd2 113.8(4) . 5_655 ? C3 N2 Cd2 130.3(5) . 5_655 ? N1 C2 C3 122.2(7) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? N2 C3 C2 121.7(7) . . ? N2 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C19 O6 Cd1 89.6(4) . 6_566 ? C18 O4 Cd2 102.1(5) . 4 ? O6 C19 O5 121.7(7) . . ? O6 C19 C15 120.9(6) . . ? O5 C19 C15 117.3(6) . . ? O6 C19 Cd1 63.3(4) . 6_566 ? O5 C19 Cd1 58.5(4) . 6_566 ? C15 C19 Cd1 175.2(5) . 6_566 ? C19 O5 Cd1 93.7(4) . 6_566 ? C21 N8 C22 117.8(8) . . ? C21 N8 C23 125.0(8) . . ? C22 N8 C23 117.0(8) . . ? O7 C21 N8 121.9(9) . . ? O7 C21 C20 121.1(8) . . ? N8 C21 C20 117.0(8) . . ? C21 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C21 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N8 C22 H22A 109.5 . . ? N8 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N8 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N8 C23 H23A 109.5 . . ? N8 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N8 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 N9 C27 136.0(17) . . ? C25 N9 C26 108.0(13) . . ? C27 N9 C26 114.6(11) . . ? N9 C25 O9 138.3(15) . . ? N9 C25 C24 105.1(13) . . ? O9 C25 C24 116.3(11) . . ? C25 C24 H24A 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C25 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N9 C26 H26A 109.5 . . ? N9 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N9 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N9 C27 H27A 109.5 . . ? N9 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N9 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.045 _refine_diff_density_min -1.038 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 926787'