# 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 _database_code_depnum_ccdc_archive 'CCDC 912022' #TrackingRef 'Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 N3 O4 Zn' _chemical_formula_weight 451.75 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 Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' 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 11.4552(13) _cell_length_b 10.586(2) _cell_length_c 18.080(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.115(3) _cell_angle_gamma 90.00 _cell_volume 2095.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 1.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7860 _exptl_absorpt_correction_T_max 0.8494 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17288 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0603 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 29.23 _reflns_number_total 5113 _reflns_number_gt 3171 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0637P)^2^+0.0000P] 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 5113 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 0.897 _refine_ls_restrained_S_all 0.897 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.21453(3) 0.02557(3) 0.469045(17) 0.03294(11) Uani 1 1 d . . . C1 C 0.0220(2) 0.0842(3) 0.33941(17) 0.0412(7) Uani 1 1 d . . . C2 C -0.0790(2) 0.1750(2) 0.29933(14) 0.0313(6) Uani 1 1 d . . . C3 C -0.1026(2) 0.1978(2) 0.22126(15) 0.0321(6) Uani 1 1 d . . . H3 H -0.0618 0.1511 0.1930 0.039 Uiso 1 1 calc R . . C4 C -0.1858(2) 0.2890(2) 0.18410(14) 0.0316(6) Uani 1 1 d . . . C5 C -0.2483(2) 0.3558(3) 0.22603(16) 0.0379(6) Uani 1 1 d . . . H5 H -0.3036 0.4182 0.2019 0.045 Uiso 1 1 calc R . . C6 C -0.2290(2) 0.3306(3) 0.30341(16) 0.0454(7) Uani 1 1 d . . . H6 H -0.2731 0.3742 0.3310 0.054 Uiso 1 1 calc R . . C7 C -0.1440(2) 0.2402(3) 0.34049(16) 0.0405(7) Uani 1 1 d . . . H7 H -0.1309 0.2236 0.3928 0.049 Uiso 1 1 calc R . . C8 C -0.2050(2) 0.3159(3) 0.09964(15) 0.0382(6) Uani 1 1 d . . . C9 C 0.1627(2) -0.2640(2) 0.45398(15) 0.0317(6) Uani 1 1 d . . . C10 C 0.0444(2) -0.2637(3) 0.40299(18) 0.0481(8) Uani 1 1 d . . . H10 H 0.0045 -0.1888 0.3838 0.058 Uiso 1 1 calc R . . C11 C -0.0101(3) -0.3790(3) 0.3826(2) 0.0583(9) Uani 1 1 d . . . H11 H -0.0890 -0.3823 0.3490 0.070 Uiso 1 1 calc R . . C12 C 0.0496(3) -0.4912(3) 0.4109(2) 0.0574(9) Uani 1 1 d . . . H12 H 0.0096 -0.5674 0.3952 0.069 Uiso 1 1 calc R . . C13 C 0.1657(3) -0.4932(3) 0.4615(2) 0.0484(8) Uani 1 1 d . . . H13 H 0.2051 -0.5683 0.4808 0.058 Uiso 1 1 calc R . . C14 C 0.2200(2) -0.3772(3) 0.48168(15) 0.0337(6) Uani 1 1 d . . . C15 C 0.3420(2) -0.2165(2) 0.53094(14) 0.0297(5) Uani 1 1 d . . . C16 C 0.4509(2) -0.1458(2) 0.57627(14) 0.0327(6) Uani 1 1 d . . . C17 C 0.5471(2) -0.1286(2) 0.54631(15) 0.0334(6) Uani 1 1 d . . . H17 H 0.5416 -0.1637 0.4983 0.040 Uiso 1 1 calc R . . C18 C 0.4584(3) -0.0930(3) 0.64763(18) 0.0567(9) Uani 1 1 d . . . H18 H 0.3954 -0.1035 0.6698 0.068 Uiso 1 1 calc R . . C19 C 0.6533(3) -0.0134(3) 0.6511(2) 0.0600(9) Uani 1 1 d . . . H19 H 0.7230 0.0316 0.6772 0.072 Uiso 1 1 calc R . . C20 C 0.5611(3) -0.0245(4) 0.6850(2) 0.0768(12) Uani 1 1 d . . . H20 H 0.5679 0.0137 0.7324 0.092 Uiso 1 1 calc R . . C21 C 0.4274(2) -0.4326(3) 0.57669(16) 0.0388(6) Uani 1 1 d . . . H21A H 0.3865 -0.5086 0.5858 0.047 Uiso 1 1 calc R . . H21B H 0.4670 -0.3946 0.6266 0.047 Uiso 1 1 calc R . . C22 C 0.5244(2) -0.4688(3) 0.53878(16) 0.0407(6) Uani 1 1 d . . . H22A H 0.5687 -0.3933 0.5327 0.049 Uiso 1 1 calc R . . H22B H 0.5821 -0.5256 0.5730 0.049 Uiso 1 1 calc R . . N1 N 0.24079(18) -0.1639(2) 0.48495(12) 0.0333(5) Uani 1 1 d . . . N2 N 0.33538(18) -0.3441(2) 0.53092(12) 0.0324(5) Uani 1 1 d . . . N3 N 0.64797(18) -0.0640(2) 0.58250(13) 0.0369(5) Uani 1 1 d . . . O1 O 0.06088(17) 0.0968(2) 0.41292(12) 0.0537(6) Uani 1 1 d . . . O2 O 0.0618(2) 0.0091(2) 0.30137(15) 0.0627(6) Uani 1 1 d . . . O3 O -0.25705(18) 0.42029(19) 0.07519(11) 0.0496(5) Uani 1 1 d . . . O4 O -0.1687(2) 0.2392(2) 0.05989(12) 0.0546(5) 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 0.03277(17) 0.03013(18) 0.03061(17) 0.00173(13) 0.00108(12) -0.00035(12) C1 0.0326(14) 0.0379(17) 0.0476(17) 0.0151(14) 0.0030(13) -0.0040(12) C2 0.0261(12) 0.0294(14) 0.0351(14) 0.0031(11) 0.0040(10) -0.0034(10) C3 0.0317(13) 0.0296(14) 0.0346(14) -0.0020(11) 0.0091(10) 0.0003(10) C4 0.0307(13) 0.0295(14) 0.0314(13) 0.0006(11) 0.0043(10) -0.0033(10) C5 0.0336(13) 0.0361(16) 0.0423(15) 0.0036(12) 0.0085(12) 0.0085(11) C6 0.0394(15) 0.057(2) 0.0434(17) -0.0027(14) 0.0185(13) 0.0103(13) C7 0.0363(14) 0.0538(18) 0.0317(14) 0.0056(13) 0.0106(11) -0.0041(13) C8 0.0402(14) 0.0363(16) 0.0325(14) 0.0024(12) 0.0019(11) -0.0083(12) C9 0.0309(13) 0.0273(14) 0.0373(14) -0.0037(11) 0.0104(10) -0.0034(10) C10 0.0375(15) 0.0400(18) 0.0583(19) 0.0032(14) 0.0008(13) 0.0007(12) C11 0.0360(16) 0.052(2) 0.074(2) -0.0050(17) -0.0029(15) -0.0066(14) C12 0.0454(18) 0.0379(19) 0.084(3) -0.0087(16) 0.0115(17) -0.0120(13) C13 0.0415(16) 0.0375(18) 0.068(2) 0.0002(14) 0.0183(14) -0.0015(12) C14 0.0325(13) 0.0306(15) 0.0412(15) -0.0017(11) 0.0156(11) -0.0022(11) C15 0.0286(12) 0.0305(15) 0.0318(13) 0.0017(11) 0.0115(10) 0.0013(10) C16 0.0321(13) 0.0310(15) 0.0328(13) 0.0013(11) 0.0061(11) 0.0039(10) C17 0.0356(14) 0.0288(14) 0.0324(13) 0.0018(11) 0.0050(11) 0.0024(10) C18 0.0436(17) 0.086(3) 0.0439(17) -0.0160(17) 0.0181(14) -0.0108(16) C19 0.0414(17) 0.083(3) 0.0516(19) -0.0232(18) 0.0079(14) -0.0168(16) C20 0.053(2) 0.128(4) 0.050(2) -0.040(2) 0.0179(16) -0.025(2) C21 0.0395(15) 0.0347(15) 0.0429(16) 0.0074(12) 0.0132(12) 0.0078(11) C22 0.0341(14) 0.0348(15) 0.0521(17) 0.0020(13) 0.0111(12) 0.0070(12) N1 0.0323(11) 0.0310(13) 0.0340(12) 0.0008(9) 0.0057(9) -0.0003(9) N2 0.0294(11) 0.0298(12) 0.0386(12) 0.0018(9) 0.0109(9) 0.0028(9) N3 0.0320(11) 0.0389(13) 0.0369(12) 0.0002(10) 0.0058(9) 0.0009(9) O1 0.0398(11) 0.0700(15) 0.0418(12) 0.0160(11) -0.0027(9) 0.0093(10) O2 0.0570(14) 0.0556(15) 0.0676(16) 0.0020(12) 0.0063(12) 0.0237(11) O3 0.0634(13) 0.0420(12) 0.0337(11) 0.0074(9) -0.0007(9) 0.0060(10) O4 0.0838(15) 0.0463(13) 0.0380(11) -0.0041(10) 0.0245(11) -0.0013(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 1.9089(18) . ? Zn1 O3 1.9364(19) 4_666 ? Zn1 N1 2.036(2) . ? Zn1 N3 2.093(2) 3_656 ? C1 O2 1.223(4) . ? C1 O1 1.278(3) . ? C1 C2 1.515(4) . ? C2 C3 1.378(3) . ? C2 C7 1.383(4) . ? C3 C4 1.384(3) . ? C3 H3 0.9300 . ? C4 C5 1.380(4) . ? C4 C8 1.505(4) . ? C5 C6 1.377(4) . ? C5 H5 0.9300 . ? C6 C7 1.389(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O4 1.234(3) . ? C8 O3 1.272(3) . ? C9 C14 1.387(4) . ? C9 N1 1.393(3) . ? C9 C10 1.397(4) . ? C10 C11 1.371(4) . ? C10 H10 0.9300 . ? C11 C12 1.390(4) . ? C11 H11 0.9300 . ? C12 C13 1.375(5) . ? C12 H12 0.9300 . ? C13 C14 1.377(4) . ? C13 H13 0.9300 . ? C14 N2 1.404(3) . ? C15 N1 1.333(3) . ? C15 N2 1.352(3) . ? C15 C16 1.479(3) . ? C16 C17 1.376(4) . ? C16 C18 1.385(4) . ? C17 N3 1.336(3) . ? C17 H17 0.9300 . ? C18 C20 1.378(5) . ? C18 H18 0.9300 . ? C19 N3 1.337(4) . ? C19 C20 1.373(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 N2 1.470(3) . ? C21 C22 1.516(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C22 1.501(6) 3_646 ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? N3 Zn1 2.093(2) 3_656 ? O3 Zn1 1.9364(19) 4_565 ? 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 105.65(9) . 4_666 ? O1 Zn1 N1 122.60(9) . . ? O3 Zn1 N1 100.19(9) 4_666 . ? O1 Zn1 N3 112.55(9) . 3_656 ? O3 Zn1 N3 117.04(9) 4_666 3_656 ? N1 Zn1 N3 98.93(9) . 3_656 ? O2 C1 O1 125.4(3) . . ? O2 C1 C2 120.1(3) . . ? O1 C1 C2 114.5(3) . . ? C3 C2 C7 119.3(2) . . ? C3 C2 C1 119.6(2) . . ? C7 C2 C1 121.1(2) . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 119.0(2) . . ? C5 C4 C8 121.1(2) . . ? C3 C4 C8 119.9(2) . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C2 C7 C6 119.8(2) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? O4 C8 O3 125.0(3) . . ? O4 C8 C4 119.6(2) . . ? O3 C8 C4 115.5(3) . . ? C14 C9 N1 109.4(2) . . ? C14 C9 C10 120.3(2) . . ? N1 C9 C10 130.3(2) . . ? C11 C10 C9 116.8(3) . . ? C11 C10 H10 121.6 . . ? C9 C10 H10 121.6 . . ? C10 C11 C12 121.7(3) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C13 C12 C11 122.2(3) . . ? C13 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? C12 C13 C14 115.8(3) . . ? C12 C13 H13 122.1 . . ? C14 C13 H13 122.1 . . ? C13 C14 C9 123.1(2) . . ? C13 C14 N2 131.2(2) . . ? C9 C14 N2 105.7(2) . . ? N1 C15 N2 112.2(2) . . ? N1 C15 C16 124.8(2) . . ? N2 C15 C16 122.9(2) . . ? C17 C16 C18 118.4(2) . . ? C17 C16 C15 119.5(2) . . ? C18 C16 C15 122.1(2) . . ? N3 C17 C16 123.5(3) . . ? N3 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? C20 C18 C16 118.6(3) . . ? C20 C18 H18 120.7 . . ? C16 C18 H18 120.7 . . ? N3 C19 C20 123.3(3) . . ? N3 C19 H19 118.4 . . ? C20 C19 H19 118.4 . . ? C19 C20 C18 119.0(3) . . ? C19 C20 H20 120.5 . . ? C18 C20 H20 120.5 . . ? N2 C21 C22 114.0(2) . . ? N2 C21 H21A 108.8 . . ? C22 C21 H21A 108.8 . . ? N2 C21 H21B 108.8 . . ? C22 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C22 C22 C21 114.4(3) 3_646 . ? C22 C22 H22A 108.7 3_646 . ? C21 C22 H22A 108.7 . . ? C22 C22 H22B 108.7 3_646 . ? C21 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C15 N1 C9 105.7(2) . . ? C15 N1 Zn1 124.38(17) . . ? C9 N1 Zn1 129.91(16) . . ? C15 N2 C14 107.0(2) . . ? C15 N2 C21 127.3(2) . . ? C14 N2 C21 125.7(2) . . ? C17 N3 C19 117.2(2) . . ? C17 N3 Zn1 122.50(19) . 3_656 ? C19 N3 Zn1 120.04(18) . 3_656 ? C1 O1 Zn1 119.75(19) . . ? C8 O3 Zn1 121.76(19) . 4_565 ? 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 O2 C1 C2 C3 -17.8(4) . . . . ? O1 C1 C2 C3 160.3(2) . . . . ? O2 C1 C2 C7 165.3(3) . . . . ? O1 C1 C2 C7 -16.5(4) . . . . ? C7 C2 C3 C4 3.2(4) . . . . ? C1 C2 C3 C4 -173.7(2) . . . . ? C2 C3 C4 C5 -1.6(4) . . . . ? C2 C3 C4 C8 177.0(2) . . . . ? C3 C4 C5 C6 -0.9(4) . . . . ? C8 C4 C5 C6 -179.6(2) . . . . ? C4 C5 C6 C7 1.9(4) . . . . ? C3 C2 C7 C6 -2.2(4) . . . . ? C1 C2 C7 C6 174.7(2) . . . . ? C5 C6 C7 C2 -0.3(4) . . . . ? C5 C4 C8 O4 -165.0(3) . . . . ? C3 C4 C8 O4 16.4(4) . . . . ? C5 C4 C8 O3 16.2(4) . . . . ? C3 C4 C8 O3 -162.4(2) . . . . ? C14 C9 C10 C11 0.0(5) . . . . ? N1 C9 C10 C11 180.0(3) . . . . ? C9 C10 C11 C12 -0.3(5) . . . . ? C10 C11 C12 C13 0.7(6) . . . . ? C11 C12 C13 C14 -0.7(5) . . . . ? C12 C13 C14 C9 0.5(5) . . . . ? C12 C13 C14 N2 180.0(3) . . . . ? N1 C9 C14 C13 179.9(3) . . . . ? C10 C9 C14 C13 -0.1(4) . . . . ? N1 C9 C14 N2 0.3(3) . . . . ? C10 C9 C14 N2 -179.7(3) . . . . ? N1 C15 C16 C17 -95.5(3) . . . . ? N2 C15 C16 C17 83.4(3) . . . . ? N1 C15 C16 C18 82.8(4) . . . . ? N2 C15 C16 C18 -98.3(3) . . . . ? C18 C16 C17 N3 0.3(4) . . . . ? C15 C16 C17 N3 178.7(2) . . . . ? C17 C16 C18 C20 0.7(5) . . . . ? C15 C16 C18 C20 -177.6(3) . . . . ? N3 C19 C20 C18 1.2(6) . . . . ? C16 C18 C20 C19 -1.5(6) . . . . ? N2 C21 C22 C22 -59.6(4) . . . 3_646 ? N2 C15 N1 C9 0.9(3) . . . . ? C16 C15 N1 C9 179.9(2) . . . . ? N2 C15 N1 Zn1 179.97(16) . . . . ? C16 C15 N1 Zn1 -1.0(4) . . . . ? C14 C9 N1 C15 -0.8(3) . . . . ? C10 C9 N1 C15 179.3(3) . . . . ? C14 C9 N1 Zn1 -179.72(17) . . . . ? C10 C9 N1 Zn1 0.3(4) . . . . ? O1 Zn1 N1 C15 -171.96(19) . . . . ? O3 Zn1 N1 C15 -55.8(2) 4_666 . . . ? N3 Zn1 N1 C15 63.9(2) 3_656 . . . ? O1 Zn1 N1 C9 6.8(3) . . . . ? O3 Zn1 N1 C9 122.9(2) 4_666 . . . ? N3 Zn1 N1 C9 -117.3(2) 3_656 . . . ? N1 C15 N2 C14 -0.8(3) . . . . ? C16 C15 N2 C14 -179.8(2) . . . . ? N1 C15 N2 C21 -177.6(2) . . . . ? C16 C15 N2 C21 3.4(4) . . . . ? C13 C14 N2 C15 -179.3(3) . . . . ? C9 C14 N2 C15 0.2(3) . . . . ? C13 C14 N2 C21 -2.5(5) . . . . ? C9 C14 N2 C21 177.1(2) . . . . ? C22 C21 N2 C15 -86.7(3) . . . . ? C22 C21 N2 C14 97.1(3) . . . . ? C16 C17 N3 C19 -0.6(4) . . . . ? C16 C17 N3 Zn1 -174.25(19) . . . 3_656 ? C20 C19 N3 C17 -0.2(5) . . . . ? C20 C19 N3 Zn1 173.6(3) . . . 3_656 ? O2 C1 O1 Zn1 15.4(4) . . . . ? C2 C1 O1 Zn1 -162.60(17) . . . . ? O3 Zn1 O1 C1 175.0(2) 4_666 . . . ? N1 Zn1 O1 C1 -71.6(2) . . . . ? N3 Zn1 O1 C1 46.2(2) 3_656 . . . ? O4 C8 O3 Zn1 -0.7(4) . . . 4_565 ? C4 C8 O3 Zn1 178.13(15) . . . 4_565 ? _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.975 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.072 data_2 _database_code_depnum_ccdc_archive 'CCDC 912023' #TrackingRef 'Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 N4 O4 Zn' _chemical_formula_weight 466.77 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 Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5009(14) _cell_length_b 10.475(2) _cell_length_c 18.115(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.417(4) _cell_angle_gamma 90.00 _cell_volume 2122.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_absorpt_coefficient_mu 1.193 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7467 _exptl_absorpt_correction_T_max 0.7963 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13155 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0866 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 26.39 _reflns_number_total 4332 _reflns_number_gt 2643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 distances of N4---H4A and N4---H4B were restrained to 0.87+-0.01 \%A. The distance of H4A...H4B was restrained to 1.40+-0.02 \%A. ; _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^)+(0.0456P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4332 _refine_ls_number_parameters 286 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 0.824 _refine_ls_restrained_S_all 0.828 _refine_ls_shift/su_max 0.003 _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 Zn1 Zn 0.25024(3) 0.01475(3) 0.031517(17) 0.02758(12) Uani 1 1 d . . . C1 C 0.1713(3) 0.0774(3) 0.16105(17) 0.0315(7) Uani 1 1 d . . . C2 C 0.1202(3) 0.1713(3) 0.20691(14) 0.0255(6) Uani 1 1 d . . . C3 C 0.1861(3) 0.2008(3) 0.27901(15) 0.0296(7) Uani 1 1 d . . . H3 H 0.2574 0.1581 0.2990 0.036 Uiso 1 1 calc R . . C4 C 0.1455(3) 0.2945(3) 0.32145(14) 0.0275(7) Uani 1 1 d . . . C5 C 0.0384(3) 0.3540(3) 0.29237(15) 0.0285(7) Uani 1 1 d . . . H5 H 0.0127 0.4187 0.3200 0.034 Uiso 1 1 calc R . . C6 C -0.0322(3) 0.3188(3) 0.22202(16) 0.0327(7) Uani 1 1 d . . . C7 C 0.0110(3) 0.2299(3) 0.17866(15) 0.0294(7) Uani 1 1 d . . . H7 H -0.0334 0.2094 0.1304 0.035 Uiso 1 1 calc R . . C8 C 0.2177(3) 0.3266(3) 0.39951(16) 0.0333(7) Uani 1 1 d . . . C9 C 0.3142(3) -0.2260(3) -0.03495(15) 0.0257(7) Uani 1 1 d . . . C10 C 0.3841(3) -0.1521(3) -0.07944(15) 0.0271(7) Uani 1 1 d . . . C11 C 0.5029(3) -0.1259(3) -0.04863(15) 0.0291(7) Uani 1 1 d . . . H11 H 0.5372 -0.1589 -0.0009 0.035 Uiso 1 1 calc R . . C12 C 0.3326(3) -0.1043(4) -0.15069(17) 0.0492(10) Uani 1 1 d . . . H12 H 0.2528 -0.1204 -0.1736 0.059 Uiso 1 1 calc R . . C13 C 0.4029(3) -0.0319(4) -0.18685(19) 0.0626(12) Uani 1 1 d . . . H13 H 0.3706 0.0015 -0.2348 0.075 Uiso 1 1 calc R . . C14 C 0.5205(3) -0.0090(3) -0.15214(18) 0.0475(9) Uani 1 1 d . . . H14 H 0.5662 0.0407 -0.1773 0.057 Uiso 1 1 calc R . . C15 C 0.2027(3) -0.2780(3) 0.04159(17) 0.0338(7) Uani 1 1 d . . . C16 C 0.2357(3) -0.3908(3) 0.01166(16) 0.0326(7) Uani 1 1 d . . . C17 C 0.1989(3) -0.5099(3) 0.0307(2) 0.0463(8) Uani 1 1 d . . . H17 H 0.2214 -0.5849 0.0104 0.056 Uiso 1 1 calc R . . C18 C 0.1269(4) -0.5100(3) 0.0816(2) 0.0631(11) Uani 1 1 d . . . H18 H 0.0996 -0.5876 0.0960 0.076 Uiso 1 1 calc R . . C19 C 0.0935(4) -0.3979(4) 0.1124(2) 0.0706(13) Uani 1 1 d . . . H19 H 0.0450 -0.4027 0.1468 0.085 Uiso 1 1 calc R . . C20 C 0.1303(4) -0.2807(3) 0.0932(2) 0.0576(11) Uani 1 1 d . . . H20 H 0.1078 -0.2060 0.1139 0.069 Uiso 1 1 calc R . . C21 C 0.3661(3) -0.4417(3) -0.08008(16) 0.0346(8) Uani 1 1 d . . . H21A H 0.3657 -0.4035 -0.1289 0.042 Uiso 1 1 calc R . . H21B H 0.3212 -0.5207 -0.0892 0.042 Uiso 1 1 calc R . . C22 C 0.4944(3) -0.4712(3) -0.03921(16) 0.0372(7) Uani 1 1 d . . . H22A H 0.5408 -0.3931 -0.0343 0.045 Uiso 1 1 calc R . . H22B H 0.5282 -0.5302 -0.0698 0.045 Uiso 1 1 calc R . . N1 N 0.2542(2) -0.1744(2) 0.01201(13) 0.0309(6) Uani 1 1 d . . . N2 N 0.3069(2) -0.3544(2) -0.03657(12) 0.0283(6) Uani 1 1 d . . . N3 N 0.5720(2) -0.0558(2) -0.08329(13) 0.0315(6) Uani 1 1 d . . . O1 O 0.1532(2) 0.0996(2) 0.09011(11) 0.0412(6) Uani 1 1 d . . . O2 O 0.23040(19) -0.01420(19) 0.19295(11) 0.0366(5) Uani 1 1 d . . . O3 O 0.3013(2) 0.2571(2) 0.43020(13) 0.0567(7) Uani 1 1 d . . . O4 O 0.1851(2) 0.4261(2) 0.42928(10) 0.0407(6) Uani 1 1 d . . . N4 N -0.1413(2) 0.3710(2) 0.19347(13) 0.0287(6) Uani 1 1 d D . . H4A H -0.180(2) 0.3096(18) 0.2026(15) 0.034 Uiso 1 1 d D . . H4B H -0.155(3) 0.4272(18) 0.2239(13) 0.034 Uiso 1 1 d 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 0.0313(2) 0.0273(2) 0.02595(17) 0.00028(15) 0.01039(13) 0.00041(17) C1 0.0261(18) 0.0312(18) 0.0401(18) -0.0077(14) 0.0136(15) -0.0072(14) C2 0.0279(17) 0.0241(16) 0.0278(15) -0.0023(12) 0.0132(13) -0.0013(13) C3 0.0284(18) 0.0288(17) 0.0316(16) 0.0043(12) 0.0068(14) 0.0040(13) C4 0.0306(18) 0.0269(16) 0.0254(15) 0.0004(12) 0.0071(13) -0.0025(13) C5 0.0344(19) 0.0253(16) 0.0279(15) -0.0010(12) 0.0113(14) 0.0029(14) C6 0.0290(19) 0.0388(19) 0.0318(16) -0.0003(14) 0.0099(14) 0.0014(15) C7 0.0318(19) 0.0329(18) 0.0231(14) -0.0039(12) 0.0060(13) -0.0025(14) C8 0.038(2) 0.0295(18) 0.0329(17) -0.0009(14) 0.0087(15) -0.0049(15) C9 0.0217(17) 0.0236(17) 0.0310(15) -0.0010(12) 0.0047(13) 0.0016(13) C10 0.0254(17) 0.0270(16) 0.0300(15) -0.0014(12) 0.0090(13) 0.0042(13) C11 0.0313(19) 0.0293(17) 0.0269(14) -0.0005(12) 0.0067(14) 0.0037(14) C12 0.025(2) 0.081(3) 0.0384(19) 0.0107(18) 0.0009(15) -0.0059(18) C13 0.037(2) 0.110(3) 0.0396(19) 0.035(2) 0.0074(16) -0.004(2) C14 0.039(2) 0.064(2) 0.0425(18) 0.0185(17) 0.0157(16) -0.0048(19) C15 0.035(2) 0.0250(18) 0.0463(18) -0.0001(14) 0.0190(15) -0.0021(14) C16 0.0285(19) 0.0259(18) 0.0450(18) 0.0013(13) 0.0120(15) -0.0034(14) C17 0.047(2) 0.0275(19) 0.069(2) 0.0009(16) 0.0228(18) -0.0013(16) C18 0.073(3) 0.035(2) 0.094(3) 0.008(2) 0.045(2) -0.009(2) C19 0.087(4) 0.042(3) 0.105(3) 0.000(2) 0.068(3) -0.014(2) C20 0.075(3) 0.035(2) 0.078(3) -0.0061(18) 0.050(2) -0.0022(19) C21 0.0333(19) 0.0344(18) 0.0358(17) -0.0061(13) 0.0075(15) 0.0074(14) C22 0.0354(19) 0.0334(18) 0.0434(17) -0.0019(14) 0.0102(15) 0.0095(15) N1 0.0359(16) 0.0216(14) 0.0398(15) -0.0010(10) 0.0183(13) -0.0009(12) N2 0.0248(14) 0.0247(14) 0.0355(13) -0.0028(11) 0.0072(11) 0.0040(11) N3 0.0294(15) 0.0335(15) 0.0338(14) 0.0018(11) 0.0124(12) -0.0008(12) O1 0.0466(15) 0.0501(15) 0.0308(12) -0.0049(10) 0.0172(10) 0.0107(11) O2 0.0368(13) 0.0313(12) 0.0464(12) -0.0019(10) 0.0190(10) 0.0030(10) O3 0.0588(18) 0.0443(14) 0.0522(15) -0.0080(11) -0.0175(13) 0.0144(13) O4 0.0530(16) 0.0437(14) 0.0251(10) -0.0086(9) 0.0083(10) 0.0012(11) N4 0.0174(14) 0.0352(15) 0.0290(13) -0.0122(11) -0.0040(11) 0.0143(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 1.927(2) . ? Zn1 O4 1.9316(19) 4_565 ? Zn1 N1 2.015(2) . ? Zn1 N3 2.086(3) 3_655 ? C1 O2 1.238(3) . ? C1 O1 1.275(3) . ? C1 C2 1.494(4) . ? C2 C7 1.385(4) . ? C2 C3 1.385(4) . ? C3 C4 1.393(4) . ? C3 H3 0.9300 . ? C4 C5 1.372(4) . ? C4 C8 1.502(4) . ? C5 C6 1.393(4) . ? C5 H5 0.9300 . ? C6 N4 1.356(4) . ? C6 C7 1.382(4) . ? C7 H7 0.9300 . ? C8 O3 1.232(4) . ? C8 O4 1.269(4) . ? C9 N1 1.328(4) . ? C9 N2 1.348(3) . ? C9 C10 1.482(4) . ? C10 C11 1.378(4) . ? C10 C12 1.383(4) . ? C11 N3 1.341(4) . ? C11 H11 0.9300 . ? C12 C13 1.380(5) . ? C12 H12 0.9300 . ? C13 C14 1.374(5) . ? C13 H13 0.9300 . ? C14 N3 1.343(4) . ? C14 H14 0.9300 . ? C15 C16 1.389(4) . ? C15 C20 1.389(5) . ? C15 N1 1.402(4) . ? C16 N2 1.382(4) . ? C16 C17 1.387(4) . ? C17 C18 1.374(5) . ? C17 H17 0.9300 . ? C18 C19 1.391(5) . ? C18 H18 0.9300 . ? C19 C20 1.370(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 N2 1.473(4) . ? C21 C22 1.521(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C22 1.521(6) 3_645 ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? N3 Zn1 2.086(3) 3_655 ? O4 Zn1 1.9316(19) 4_566 ? N4 H4A 0.822(10) . ? N4 H4B 0.844(10) . ? 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 O4 103.58(9) . 4_565 ? O1 Zn1 N1 126.16(9) . . ? O4 Zn1 N1 99.61(9) 4_565 . ? O1 Zn1 N3 106.85(9) . 3_655 ? O4 Zn1 N3 119.09(10) 4_565 3_655 ? N1 Zn1 N3 102.79(10) . 3_655 ? O2 C1 O1 123.8(3) . . ? O2 C1 C2 119.7(3) . . ? O1 C1 C2 116.5(3) . . ? C7 C2 C3 120.1(3) . . ? C7 C2 C1 121.8(2) . . ? C3 C2 C1 118.1(3) . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.6(2) . . ? C5 C4 C8 120.7(3) . . ? C3 C4 C8 119.7(3) . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? N4 C6 C7 118.5(3) . . ? N4 C6 C5 122.2(3) . . ? C7 C6 C5 119.2(3) . . ? C6 C7 C2 120.2(3) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? O3 C8 O4 124.8(3) . . ? O3 C8 C4 119.7(3) . . ? O4 C8 C4 115.5(3) . . ? N1 C9 N2 112.4(2) . . ? N1 C9 C10 124.3(2) . . ? N2 C9 C10 123.3(2) . . ? C11 C10 C12 118.4(3) . . ? C11 C10 C9 119.7(2) . . ? C12 C10 C9 121.9(3) . . ? N3 C11 C10 124.0(3) . . ? N3 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? C13 C12 C10 118.1(3) . . ? C13 C12 H12 121.0 . . ? C10 C12 H12 121.0 . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? N3 C14 C13 122.4(3) . . ? N3 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C16 C15 C20 120.5(3) . . ? C16 C15 N1 109.3(3) . . ? C20 C15 N1 130.2(3) . . ? N2 C16 C15 105.6(2) . . ? N2 C16 C17 131.7(3) . . ? C15 C16 C17 122.7(3) . . ? C18 C17 C16 115.8(3) . . ? C18 C17 H17 122.1 . . ? C16 C17 H17 122.1 . . ? C17 C18 C19 122.1(3) . . ? C17 C18 H18 118.9 . . ? C19 C18 H18 118.9 . . ? C20 C19 C18 121.7(4) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C15 117.2(3) . . ? C19 C20 H20 121.4 . . ? C15 C20 H20 121.4 . . ? N2 C21 C22 112.5(2) . . ? N2 C21 H21A 109.1 . . ? C22 C21 H21A 109.1 . . ? N2 C21 H21B 109.1 . . ? C22 C21 H21B 109.1 . . ? H21A C21 H21B 107.8 . . ? C21 C22 C22 113.4(3) . 3_645 ? C21 C22 H22A 108.9 . . ? C22 C22 H22A 108.9 3_645 . ? C21 C22 H22B 108.9 . . ? C22 C22 H22B 108.9 3_645 . ? H22A C22 H22B 107.7 . . ? C9 N1 C15 105.0(2) . . ? C9 N1 Zn1 123.30(19) . . ? C15 N1 Zn1 131.73(19) . . ? C9 N2 C16 107.8(2) . . ? C9 N2 C21 126.6(2) . . ? C16 N2 C21 125.6(2) . . ? C11 N3 C14 117.0(3) . . ? C11 N3 Zn1 121.86(19) . 3_655 ? C14 N3 Zn1 121.1(2) . 3_655 ? C1 O1 Zn1 119.37(19) . . ? C8 O4 Zn1 125.7(2) . 4_566 ? C6 N4 H4A 96(2) . . ? C6 N4 H4B 109(2) . . ? H4A N4 H4B 103(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 O2 C1 C2 C7 -145.3(3) . . . . ? O1 C1 C2 C7 36.5(4) . . . . ? O2 C1 C2 C3 35.8(4) . . . . ? O1 C1 C2 C3 -142.4(3) . . . . ? C7 C2 C3 C4 -3.5(4) . . . . ? C1 C2 C3 C4 175.5(3) . . . . ? C2 C3 C4 C5 2.1(4) . . . . ? C2 C3 C4 C8 -179.7(3) . . . . ? C3 C4 C5 C6 2.2(4) . . . . ? C8 C4 C5 C6 -175.9(3) . . . . ? C4 C5 C6 N4 176.5(3) . . . . ? C4 C5 C6 C7 -5.2(4) . . . . ? N4 C6 C7 C2 -177.8(3) . . . . ? C5 C6 C7 C2 3.8(4) . . . . ? C3 C2 C7 C6 0.5(4) . . . . ? C1 C2 C7 C6 -178.4(3) . . . . ? C5 C4 C8 O3 166.6(3) . . . . ? C3 C4 C8 O3 -11.5(4) . . . . ? C5 C4 C8 O4 -12.8(4) . . . . ? C3 C4 C8 O4 169.1(3) . . . . ? N1 C9 C10 C11 89.5(4) . . . . ? N2 C9 C10 C11 -89.0(3) . . . . ? N1 C9 C10 C12 -88.3(4) . . . . ? N2 C9 C10 C12 93.3(4) . . . . ? C12 C10 C11 N3 0.5(4) . . . . ? C9 C10 C11 N3 -177.3(3) . . . . ? C11 C10 C12 C13 -0.5(5) . . . . ? C9 C10 C12 C13 177.3(3) . . . . ? C10 C12 C13 C14 0.0(6) . . . . ? C12 C13 C14 N3 0.6(6) . . . . ? C20 C15 C16 N2 -179.7(3) . . . . ? N1 C15 C16 N2 -0.4(3) . . . . ? C20 C15 C16 C17 0.4(5) . . . . ? N1 C15 C16 C17 179.6(3) . . . . ? N2 C16 C17 C18 -180.0(3) . . . . ? C15 C16 C17 C18 -0.1(5) . . . . ? C16 C17 C18 C19 -0.3(6) . . . . ? C17 C18 C19 C20 0.3(7) . . . . ? C18 C19 C20 C15 0.0(7) . . . . ? C16 C15 C20 C19 -0.3(6) . . . . ? N1 C15 C20 C19 -179.5(4) . . . . ? N2 C21 C22 C22 57.4(4) . . . 3_645 ? N2 C9 N1 C15 -1.2(3) . . . . ? C10 C9 N1 C15 -179.8(3) . . . . ? N2 C9 N1 Zn1 177.82(17) . . . . ? C10 C9 N1 Zn1 -0.8(4) . . . . ? C16 C15 N1 C9 1.0(3) . . . . ? C20 C15 N1 C9 -179.8(4) . . . . ? C16 C15 N1 Zn1 -177.9(2) . . . . ? C20 C15 N1 Zn1 1.3(6) . . . . ? O1 Zn1 N1 C9 173.2(2) . . . . ? O4 Zn1 N1 C9 58.4(2) 4_565 . . . ? N3 Zn1 N1 C9 -64.6(2) 3_655 . . . ? O1 Zn1 N1 C15 -8.1(3) . . . . ? O4 Zn1 N1 C15 -122.9(3) 4_565 . . . ? N3 Zn1 N1 C15 114.1(3) 3_655 . . . ? N1 C9 N2 C16 0.9(3) . . . . ? C10 C9 N2 C16 179.6(3) . . . . ? N1 C9 N2 C21 -177.6(3) . . . . ? C10 C9 N2 C21 1.1(4) . . . . ? C15 C16 N2 C9 -0.3(3) . . . . ? C17 C16 N2 C9 179.6(3) . . . . ? C15 C16 N2 C21 178.2(3) . . . . ? C17 C16 N2 C21 -1.8(5) . . . . ? C22 C21 N2 C9 83.4(3) . . . . ? C22 C21 N2 C16 -94.8(3) . . . . ? C10 C11 N3 C14 0.0(4) . . . . ? C10 C11 N3 Zn1 177.8(2) . . . 3_655 ? C13 C14 N3 C11 -0.6(5) . . . . ? C13 C14 N3 Zn1 -178.4(3) . . . 3_655 ? O2 C1 O1 Zn1 -15.4(4) . . . . ? C2 C1 O1 Zn1 162.72(19) . . . . ? O4 Zn1 O1 C1 177.9(2) 4_565 . . . ? N1 Zn1 O1 C1 65.0(2) . . . . ? N3 Zn1 O1 C1 -55.5(2) 3_655 . . . ? O3 C8 O4 Zn1 -4.8(5) . . . 4_566 ? C4 C8 O4 Zn1 174.59(19) . . . 4_566 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4B O2 0.844(10) 2.004(16) 2.776(3) 152(2) 2 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.437 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.065 data_3 _database_code_depnum_ccdc_archive 'CCDC 912024' #TrackingRef 'Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H40 N6 O14 Zn3' _chemical_formula_weight 1169.01 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 Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.1367(16) _cell_length_b 9.579(2) _cell_length_c 18.531(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.767(3) _cell_angle_gamma 90.00 _cell_volume 2668.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 1.407 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7378 _exptl_absorpt_correction_T_max 0.8062 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16523 _diffrn_reflns_av_R_equivalents 0.0870 _diffrn_reflns_av_sigmaI/netI 0.1572 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.26 _diffrn_reflns_theta_max 26.39 _reflns_number_total 5429 _reflns_number_gt 2705 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 distances of O1W---H1A and O2W---H2A were restrained to 0.87+-0.02 \%A. The distance of H1A...H2A was restrained to 2.10+-0.02 \%A. ; _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^)+(0.0526P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5429 _refine_ls_number_parameters 356 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1197 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 0.818 _refine_ls_restrained_S_all 0.820 _refine_ls_shift/su_max 0.010 _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 Zn1 Zn 0.71289(4) 0.03704(6) 1.02598(3) 0.03105(17) Uani 1 1 d . . . Zn2 Zn 0.5000 0.0000 1.0000 0.0297(2) Uani 1 2 d S . . C1 C 0.6263(4) -0.3999(5) 0.6322(2) 0.0336(12) Uani 1 1 d . . . C2 C 0.6285(3) -0.3271(5) 0.7050(2) 0.0344(12) Uani 1 1 d . . . C3 C 0.5537(4) -0.3243(6) 0.7405(3) 0.0475(15) Uani 1 1 d . . . H3 H 0.5010 -0.3648 0.7195 0.057 Uiso 1 1 calc R . . C4 C 0.5576(4) -0.2607(6) 0.8078(3) 0.0493(15) Uani 1 1 d . . . H4 H 0.5075 -0.2601 0.8325 0.059 Uiso 1 1 calc R . . C5 C 0.6341(4) -0.1986(5) 0.8383(2) 0.0367(12) Uani 1 1 d . . . C6 C 0.7083(4) -0.1968(7) 0.8021(3) 0.067(2) Uani 1 1 d . . . H6 H 0.7599 -0.1517 0.8220 0.080 Uiso 1 1 calc R . . C7 C 0.7050(4) -0.2635(7) 0.7350(3) 0.0662(19) Uani 1 1 d . . . H7 H 0.7552 -0.2649 0.7105 0.079 Uiso 1 1 calc R . . C8 C 0.6392(4) -0.1293(5) 0.9128(2) 0.0388(13) Uani 1 1 d . . . C9 C 0.6119(4) 0.2652(5) 1.0427(3) 0.0397(13) Uani 1 1 d . . . C10 C 0.5537(3) 0.3861(5) 1.0209(2) 0.0337(12) Uani 1 1 d . . . C11 C 0.5059(4) 0.3912(5) 0.9517(2) 0.0416(13) Uani 1 1 d . . . H11 H 0.5096 0.3176 0.9194 0.050 Uiso 1 1 calc R . . C12 C 0.4533(4) 0.5052(5) 0.9312(3) 0.0433(13) Uani 1 1 d . . . H12 H 0.4223 0.5089 0.8848 0.052 Uiso 1 1 calc R . . C13 C 0.8703(4) 0.1905(6) 0.9860(3) 0.0524(16) Uani 1 1 d . . . C14 C 0.8245(5) 0.2215(6) 0.9142(3) 0.0576(16) Uani 1 1 d . C . C15 C 0.7582(5) 0.3207(9) 0.9061(4) 0.084(2) Uani 1 1 d . . . H15 H 0.7437 0.3840 0.9408 0.100 Uiso 1 1 calc R A 1 C16 C 0.8470(6) 0.1523(7) 0.8538(4) 0.089(2) Uani 1 1 d . . . H16 H 0.8941 0.0893 0.8598 0.107 Uiso 1 1 calc R C . C17 C 0.8056(7) 0.1709(8) 0.7885(4) 0.082(2) Uani 1 1 d . C . H17 H 0.8226 0.1215 0.7492 0.099 Uiso 1 1 calc R . . C18 C 0.7423(8) 0.2569(14) 0.7797(4) 0.116(4) Uani 1 1 d . . . H18 H 0.7215 0.2818 0.7322 0.139 Uiso 1 1 calc R B 1 C19 C 0.9738(4) 0.1876(7) 1.0817(4) 0.0634(17) Uani 1 1 d . . . C20 C 1.0460(5) 0.2069(8) 1.1336(5) 0.092(2) Uani 1 1 d . . . H20 H 1.0959 0.2563 1.1232 0.110 Uiso 1 1 calc R . . C21 C 1.0413(5) 0.1516(8) 1.1998(4) 0.086(2) Uani 1 1 d . . . H21 H 1.0900 0.1611 1.2350 0.103 Uiso 1 1 calc R . . C22 C 0.9681(5) 0.0819(8) 1.2177(4) 0.082(2) Uani 1 1 d . . . H22 H 0.9678 0.0474 1.2646 0.098 Uiso 1 1 calc R . . C23 C 0.8931(4) 0.0617(7) 1.1660(3) 0.0624(17) Uani 1 1 d . . . H23 H 0.8432 0.0130 1.1770 0.075 Uiso 1 1 calc R . . C24 C 0.8981(4) 0.1186(6) 1.0980(3) 0.0470(14) Uani 1 1 d . . . C25 C 1.0143(5) 0.3110(8) 0.9681(4) 0.095(3) Uani 1 1 d . . . H25A H 1.0083 0.2770 0.9185 0.114 Uiso 1 1 calc R . . H25B H 1.0754 0.2957 0.9889 0.114 Uiso 1 1 calc R . . C26 C 0.9948(8) 0.4697(10) 0.9673(4) 0.135(4) Uani 1 1 d . . . H26A H 1.0338 0.5153 0.9367 0.163 Uiso 1 1 calc R . . H26B H 0.9340 0.4846 0.9455 0.163 Uiso 1 1 calc R . . N1 N 0.8346(3) 0.1218(4) 1.0376(2) 0.0379(10) Uani 1 1 d . . . N2 N 0.9550(4) 0.2304(5) 1.0096(3) 0.0672(15) Uani 1 1 d . . . N3 N 0.7102(17) 0.304(7) 0.822(2) 0.116(14) Uiso 0.39(8) 1 d P C 1 N3' N 0.7114(10) 0.364(4) 0.8405(13) 0.104(9) Uiso 0.61(8) 1 d P C 2 O1 O 0.7111(2) -0.0699(4) 0.93573(16) 0.0449(9) Uani 1 1 d . . . O2 O 0.5708(2) -0.1359(3) 0.94499(16) 0.0381(8) Uani 1 1 d . . . O3 O 0.6064(2) 0.1555(3) 1.00040(15) 0.0336(8) Uani 1 1 d . . . O4 O 0.6656(3) 0.2677(4) 1.0981(2) 0.0642(12) Uani 1 1 d . . . O5 O 0.7005(2) -0.4177(4) 0.60874(16) 0.0430(9) Uani 1 1 d . . . O6 O 0.5524(2) -0.4336(4) 0.60147(15) 0.0389(8) Uani 1 1 d . . . O1W O 0.8231(6) 0.0519(8) 0.6471(4) 0.064(2) Uani 0.50 1 d PD . . H1A H 0.802(2) -0.014(3) 0.6302(17) 0.000(10) Uiso 1 1 d D . . O2W O 0.7678(8) -0.1336(10) 0.5253(6) 0.106(4) Uani 0.50 1 d PD . . H2A H 0.788(6) -0.052(4) 0.5179(19) 0.159 Uiso 1 1 d 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 0.0380(4) 0.0348(3) 0.0201(3) 0.0003(2) 0.0025(2) -0.0018(3) Zn2 0.0364(5) 0.0361(5) 0.0166(3) -0.0002(3) 0.0024(3) 0.0036(4) C1 0.045(4) 0.035(3) 0.021(2) -0.001(2) 0.003(3) 0.009(3) C2 0.040(3) 0.041(3) 0.021(2) -0.006(2) 0.000(2) -0.003(3) C3 0.044(4) 0.067(4) 0.032(3) -0.017(3) 0.007(3) -0.013(3) C4 0.052(4) 0.065(4) 0.033(3) -0.013(3) 0.018(3) -0.011(3) C5 0.037(3) 0.046(3) 0.027(2) -0.009(2) 0.003(2) 0.002(3) C6 0.035(4) 0.112(5) 0.054(4) -0.048(4) 0.007(3) -0.016(4) C7 0.053(4) 0.103(5) 0.046(3) -0.042(3) 0.017(3) -0.016(4) C8 0.051(4) 0.035(3) 0.030(3) -0.001(2) 0.002(3) 0.009(3) C9 0.045(4) 0.038(3) 0.036(3) -0.003(3) 0.004(3) -0.006(3) C10 0.044(3) 0.023(3) 0.033(2) -0.002(2) 0.000(2) -0.001(2) C11 0.063(4) 0.027(3) 0.034(3) -0.007(2) 0.001(3) -0.001(3) C12 0.060(4) 0.032(3) 0.035(2) 0.000(2) -0.005(2) 0.001(3) C13 0.058(5) 0.052(4) 0.048(3) 0.000(3) 0.012(3) -0.012(3) C14 0.067(5) 0.055(4) 0.052(4) 0.011(3) 0.010(3) -0.014(4) C15 0.081(6) 0.118(7) 0.053(4) 0.018(4) 0.008(4) 0.000(5) C16 0.130(8) 0.072(5) 0.065(5) 0.005(4) 0.010(5) 0.001(5) C17 0.126(8) 0.087(6) 0.035(4) 0.001(4) 0.015(4) 0.005(5) C18 0.141(10) 0.162(11) 0.041(4) 0.011(6) 0.004(6) -0.036(8) C19 0.040(4) 0.062(4) 0.085(5) 0.003(4) -0.005(4) -0.005(3) C20 0.046(5) 0.087(6) 0.138(7) 0.025(5) -0.010(5) -0.013(4) C21 0.057(5) 0.096(6) 0.096(6) 0.002(5) -0.025(4) -0.014(5) C22 0.074(5) 0.110(6) 0.057(4) 0.002(4) -0.014(4) 0.000(5) C23 0.062(4) 0.075(4) 0.049(3) -0.001(3) -0.005(3) -0.012(4) C24 0.043(4) 0.046(3) 0.051(3) -0.007(3) -0.003(3) -0.004(3) C25 0.071(5) 0.094(6) 0.122(6) 0.015(5) 0.024(5) -0.051(5) C26 0.178(9) 0.113(8) 0.127(8) 0.022(7) 0.062(9) -0.074(7) N1 0.043(3) 0.036(2) 0.035(2) -0.0063(19) 0.004(2) -0.011(2) N2 0.052(4) 0.069(4) 0.080(4) 0.024(3) 0.006(3) -0.013(3) O1 0.041(2) 0.065(3) 0.0291(17) -0.0180(17) 0.0065(17) -0.003(2) O2 0.045(2) 0.0378(19) 0.0328(17) -0.0159(15) 0.0115(18) -0.0056(17) O3 0.043(2) 0.0289(18) 0.0287(17) -0.0050(14) 0.0036(16) -0.0058(16) O4 0.081(3) 0.045(2) 0.059(2) -0.017(2) -0.025(2) 0.014(2) O5 0.043(2) 0.056(2) 0.0303(17) -0.0161(17) 0.0060(17) 0.0037(19) O6 0.044(2) 0.053(2) 0.0189(15) -0.0069(15) -0.0007(16) -0.0012(19) O1W 0.100(7) 0.040(5) 0.049(4) -0.019(4) -0.003(4) -0.013(5) O2W 0.101(9) 0.072(7) 0.153(10) -0.037(7) 0.051(8) -0.023(6) _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 O5 1.940(3) 4_556 ? Zn1 O1 1.958(3) . ? Zn1 O3 1.982(3) . ? Zn1 N1 2.001(4) . ? Zn2 O2 2.035(3) 3_657 ? Zn2 O2 2.035(3) . ? Zn2 O6 2.054(3) 2_656 ? Zn2 O6 2.054(3) 4_556 ? Zn2 O3 2.193(3) 3_657 ? Zn2 O3 2.193(3) . ? C1 O6 1.236(6) . ? C1 O5 1.264(6) . ? C1 C2 1.515(6) . ? C2 C7 1.366(7) . ? C2 C3 1.376(7) . ? C3 C4 1.382(6) . ? C3 H3 0.9300 . ? C4 C5 1.364(7) . ? C4 H4 0.9300 . ? C5 C6 1.376(7) . ? C5 C8 1.525(6) . ? C6 C7 1.393(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O2 1.255(6) . ? C8 O1 1.258(6) . ? C9 O4 1.233(6) . ? C9 O3 1.307(5) . ? C9 C10 1.482(7) . ? C10 C12 1.380(6) 3_667 ? C10 C11 1.398(6) . ? C11 C12 1.378(7) . ? C11 H11 0.9300 . ? C12 C10 1.380(6) 3_667 ? C12 H12 0.9300 . ? C13 N1 1.327(6) . ? C13 N2 1.360(8) . ? C13 C14 1.457(8) . ? C14 C16 1.377(8) . ? C14 C15 1.378(9) . ? C15 N3' 1.394(16) . ? C15 N3 1.64(5) . ? C15 H15 0.9300 . ? C16 C17 1.309(10) . ? C16 H16 0.9300 . ? C17 C18 1.260(12) . ? C17 H17 0.9300 . ? C18 N3 1.07(6) . ? C18 N3' 1.63(4) . ? C18 H18 0.9300 . ? C19 C20 1.380(10) . ? C19 C24 1.386(8) . ? C19 N2 1.395(8) . ? C20 C21 1.346(9) . ? C20 H20 0.9300 . ? C21 C22 1.367(9) . ? C21 H21 0.9300 . ? C22 C23 1.410(9) . ? C22 H22 0.9300 . ? C23 C24 1.384(7) . ? C23 H23 0.9300 . ? C24 N1 1.387(7) . ? C25 N2 1.468(7) . ? C25 C26 1.548(12) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C26 1.335(15) 3_767 ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? O5 Zn1 1.940(3) 4 ? O6 Zn2 2.054(3) 2_646 ? O1W H1A 0.762(18) . ? O2W H2A 0.86(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 O5 Zn1 O1 111.97(15) 4_556 . ? O5 Zn1 O3 112.03(13) 4_556 . ? O1 Zn1 O3 99.57(14) . . ? O5 Zn1 N1 109.09(16) 4_556 . ? O1 Zn1 N1 102.95(15) . . ? O3 Zn1 N1 120.38(15) . . ? O2 Zn2 O2 180.00(14) 3_657 . ? O2 Zn2 O6 95.22(13) 3_657 2_656 ? O2 Zn2 O6 84.78(13) . 2_656 ? O2 Zn2 O6 84.78(13) 3_657 4_556 ? O2 Zn2 O6 95.22(13) . 4_556 ? O6 Zn2 O6 180.000(1) 2_656 4_556 ? O2 Zn2 O3 90.36(12) 3_657 3_657 ? O2 Zn2 O3 89.64(12) . 3_657 ? O6 Zn2 O3 90.16(12) 2_656 3_657 ? O6 Zn2 O3 89.84(12) 4_556 3_657 ? O2 Zn2 O3 89.64(12) 3_657 . ? O2 Zn2 O3 90.36(12) . . ? O6 Zn2 O3 89.84(12) 2_656 . ? O6 Zn2 O3 90.16(12) 4_556 . ? O3 Zn2 O3 180.00(16) 3_657 . ? O6 C1 O5 126.7(4) . . ? O6 C1 C2 117.1(4) . . ? O5 C1 C2 116.2(5) . . ? C7 C2 C3 120.1(4) . . ? C7 C2 C1 119.8(4) . . ? C3 C2 C1 120.1(5) . . ? C2 C3 C4 119.4(5) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.7(5) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.4(4) . . ? C4 C5 C8 121.0(5) . . ? C6 C5 C8 118.6(5) . . ? C5 C6 C7 118.9(6) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C2 C7 C6 120.5(5) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? O2 C8 O1 126.2(4) . . ? O2 C8 C5 116.8(5) . . ? O1 C8 C5 116.9(5) . . ? O4 C9 O3 120.3(5) . . ? O4 C9 C10 121.6(5) . . ? O3 C9 C10 118.1(4) . . ? C12 C10 C11 119.6(4) 3_667 . ? C12 C10 C9 120.2(4) 3_667 . ? C11 C10 C9 120.2(4) . . ? C12 C11 C10 120.0(4) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C10 120.4(4) . 3_667 ? C11 C12 H12 119.8 . . ? C10 C12 H12 119.8 3_667 . ? N1 C13 N2 110.9(5) . . ? N1 C13 C14 124.7(5) . . ? N2 C13 C14 124.4(5) . . ? C16 C14 C15 119.3(7) . . ? C16 C14 C13 120.5(7) . . ? C15 C14 C13 120.1(6) . . ? C14 C15 N3' 126.0(16) . . ? C14 C15 N3 106(2) . . ? N3' C15 N3 23.4(12) . . ? C14 C15 H15 127.1 . . ? N3' C15 H15 105.9 . . ? N3 C15 H15 127.1 . . ? C17 C16 C14 123.3(8) . . ? C17 C16 H16 118.3 . . ? C14 C16 H16 118.3 . . ? C18 C17 C16 118.9(8) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? N3 C18 C17 125.6(18) . . ? N3 C18 N3' 16(3) . . ? C17 C18 N3' 126.6(8) . . ? N3 C18 H18 117.2 . . ? C17 C18 H18 117.2 . . ? N3' C18 H18 113.7 . . ? C20 C19 C24 121.3(6) . . ? C20 C19 N2 133.1(7) . . ? C24 C19 N2 105.5(6) . . ? C21 C20 C19 117.3(7) . . ? C21 C20 H20 121.3 . . ? C19 C20 H20 121.3 . . ? C20 C21 C22 123.0(7) . . ? C20 C21 H21 118.5 . . ? C22 C21 H21 118.5 . . ? C21 C22 C23 120.8(7) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C24 C23 C22 116.0(6) . . ? C24 C23 H23 122.0 . . ? C22 C23 H23 122.0 . . ? C23 C24 C19 121.4(6) . . ? C23 C24 N1 129.5(5) . . ? C19 C24 N1 109.1(5) . . ? N2 C25 C26 113.2(6) . . ? N2 C25 H25A 108.9 . . ? C26 C25 H25A 108.9 . . ? N2 C25 H25B 108.9 . . ? C26 C25 H25B 108.9 . . ? H25A C25 H25B 107.8 . . ? C26 C26 C25 114.6(12) 3_767 . ? C26 C26 H26A 108.6 3_767 . ? C25 C26 H26A 108.6 . . ? C26 C26 H26B 108.6 3_767 . ? C25 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? C13 N1 C24 106.8(5) . . ? C13 N1 Zn1 124.8(4) . . ? C24 N1 Zn1 128.3(3) . . ? C13 N2 C19 107.6(5) . . ? C13 N2 C25 126.3(6) . . ? C19 N2 C25 126.0(6) . . ? C18 N3 C15 123(2) . . ? C15 N3' C18 105.1(18) . . ? C8 O1 Zn1 116.7(3) . . ? C8 O2 Zn2 135.9(3) . . ? C9 O3 Zn1 108.9(3) . . ? C9 O3 Zn2 122.8(3) . . ? Zn1 O3 Zn2 100.84(13) . . ? C1 O5 Zn1 121.6(3) . 4 ? C1 O6 Zn2 137.2(3) . 2_646 ? 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 O6 C1 C2 C7 -167.4(5) . . . . ? O5 C1 C2 C7 11.4(7) . . . . ? O6 C1 C2 C3 12.3(7) . . . . ? O5 C1 C2 C3 -168.9(5) . . . . ? C7 C2 C3 C4 -2.1(8) . . . . ? C1 C2 C3 C4 178.3(5) . . . . ? C2 C3 C4 C5 1.3(8) . . . . ? C3 C4 C5 C6 0.9(9) . . . . ? C3 C4 C5 C8 -179.5(5) . . . . ? C4 C5 C6 C7 -2.3(10) . . . . ? C8 C5 C6 C7 178.1(5) . . . . ? C3 C2 C7 C6 0.7(9) . . . . ? C1 C2 C7 C6 -179.6(5) . . . . ? C5 C6 C7 C2 1.5(10) . . . . ? C4 C5 C8 O2 2.0(7) . . . . ? C6 C5 C8 O2 -178.3(5) . . . . ? C4 C5 C8 O1 -177.3(5) . . . . ? C6 C5 C8 O1 2.3(7) . . . . ? O4 C9 C10 C12 -11.7(8) . . . 3_667 ? O3 C9 C10 C12 169.8(4) . . . 3_667 ? O4 C9 C10 C11 167.9(5) . . . . ? O3 C9 C10 C11 -10.5(7) . . . . ? C12 C10 C11 C12 1.0(8) 3_667 . . . ? C9 C10 C11 C12 -178.6(5) . . . . ? C10 C11 C12 C10 -1.0(9) . . . 3_667 ? N1 C13 C14 C16 -108.0(7) . . . . ? N2 C13 C14 C16 73.3(9) . . . . ? N1 C13 C14 C15 72.1(8) . . . . ? N2 C13 C14 C15 -106.7(8) . . . . ? C16 C14 C15 N3' -2.2(17) . . . . ? C13 C14 C15 N3' 177.8(14) . . . . ? C16 C14 C15 N3 11.0(17) . . . . ? C13 C14 C15 N3 -169.0(15) . . . . ? C15 C14 C16 C17 -3.4(11) . . . . ? C13 C14 C16 C17 176.7(7) . . . . ? C14 C16 C17 C18 0.5(14) . . . . ? C16 C17 C18 N3 -12(4) . . . . ? C16 C17 C18 N3' 7.2(19) . . . . ? C24 C19 C20 C21 2.5(11) . . . . ? N2 C19 C20 C21 178.9(7) . . . . ? C19 C20 C21 C22 -1.9(12) . . . . ? C20 C21 C22 C23 1.4(12) . . . . ? C21 C22 C23 C24 -1.3(10) . . . . ? C22 C23 C24 C19 1.8(9) . . . . ? C22 C23 C24 N1 -176.7(6) . . . . ? C20 C19 C24 C23 -2.5(10) . . . . ? N2 C19 C24 C23 -179.8(5) . . . . ? C20 C19 C24 N1 176.3(6) . . . . ? N2 C19 C24 N1 -1.0(7) . . . . ? N2 C25 C26 C26 61.8(15) . . . 3_767 ? N2 C13 N1 C24 1.0(6) . . . . ? C14 C13 N1 C24 -177.9(6) . . . . ? N2 C13 N1 Zn1 -177.5(4) . . . . ? C14 C13 N1 Zn1 3.6(8) . . . . ? C23 C24 N1 C13 178.7(6) . . . . ? C19 C24 N1 C13 0.0(6) . . . . ? C23 C24 N1 Zn1 -2.8(8) . . . . ? C19 C24 N1 Zn1 178.5(4) . . . . ? O5 Zn1 N1 C13 168.7(4) 4_556 . . . ? O1 Zn1 N1 C13 49.6(4) . . . . ? O3 Zn1 N1 C13 -59.8(4) . . . . ? O5 Zn1 N1 C24 -9.5(5) 4_556 . . . ? O1 Zn1 N1 C24 -128.6(4) . . . . ? O3 Zn1 N1 C24 122.0(4) . . . . ? N1 C13 N2 C19 -1.6(7) . . . . ? C14 C13 N2 C19 177.3(6) . . . . ? N1 C13 N2 C25 -178.5(6) . . . . ? C14 C13 N2 C25 0.4(10) . . . . ? C20 C19 N2 C13 -175.3(8) . . . . ? C24 C19 N2 C13 1.6(7) . . . . ? C20 C19 N2 C25 1.6(12) . . . . ? C24 C19 N2 C25 178.4(6) . . . . ? C26 C25 N2 C13 79.8(9) . . . . ? C26 C25 N2 C19 -96.5(9) . . . . ? C17 C18 N3 C15 24(7) . . . . ? N3' C18 N3 C15 -76(7) . . . . ? C14 C15 N3 C18 -22(5) . . . . ? N3' C15 N3 C18 130(7) . . . . ? C14 C15 N3' C18 8(2) . . . . ? N3 C15 N3' C18 -26(3) . . . . ? N3 C18 N3' C15 81(7) . . . . ? C17 C18 N3' C15 -11(2) . . . . ? O2 C8 O1 Zn1 -6.1(7) . . . . ? C5 C8 O1 Zn1 173.2(3) . . . . ? O5 Zn1 O1 C8 66.7(4) 4_556 . . . ? O3 Zn1 O1 C8 -51.9(4) . . . . ? N1 Zn1 O1 C8 -176.3(4) . . . . ? O1 C8 O2 Zn2 45.0(8) . . . . ? C5 C8 O2 Zn2 -134.4(4) . . . . ? O2 Zn2 O2 C8 -118(100) 3_657 . . . ? O6 Zn2 O2 C8 78.8(5) 2_656 . . . ? O6 Zn2 O2 C8 -101.2(5) 4_556 . . . ? O3 Zn2 O2 C8 169.0(5) 3_657 . . . ? O3 Zn2 O2 C8 -11.0(5) . . . . ? O4 C9 O3 Zn1 -15.0(6) . . . . ? C10 C9 O3 Zn1 163.5(3) . . . . ? O4 C9 O3 Zn2 102.3(5) . . . . ? C10 C9 O3 Zn2 -79.2(5) . . . . ? O5 Zn1 O3 C9 82.3(3) 4_556 . . . ? O1 Zn1 O3 C9 -159.1(3) . . . . ? N1 Zn1 O3 C9 -47.9(3) . . . . ? O5 Zn1 O3 Zn2 -48.15(16) 4_556 . . . ? O1 Zn1 O3 Zn2 70.36(14) . . . . ? N1 Zn1 O3 Zn2 -178.40(13) . . . . ? O2 Zn2 O3 C9 15.1(4) 3_657 . . . ? O2 Zn2 O3 C9 -164.9(4) . . . . ? O6 Zn2 O3 C9 110.3(4) 2_656 . . . ? O6 Zn2 O3 C9 -69.7(4) 4_556 . . . ? O3 Zn2 O3 C9 -135.1(12) 3_657 . . . ? O2 Zn2 O3 Zn1 136.22(13) 3_657 . . . ? O2 Zn2 O3 Zn1 -43.78(13) . . . . ? O6 Zn2 O3 Zn1 -128.55(13) 2_656 . . . ? O6 Zn2 O3 Zn1 51.45(13) 4_556 . . . ? O3 Zn2 O3 Zn1 -14.0(11) 3_657 . . . ? O6 C1 O5 Zn1 -12.5(7) . . . 4 ? C2 C1 O5 Zn1 168.9(3) . . . 4 ? O5 C1 O6 Zn2 -11.7(8) . . . 2_646 ? C2 C1 O6 Zn2 166.9(3) . . . 2_646 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1A O2W 0.762(18) 2.26(3) 2.916(13) 145(3) . O2W H2A O1W 0.86(2) 2.59(4) 2.916(13) 104(3) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.654 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.083 data_4 _database_code_depnum_ccdc_archive 'CCDC 912025' #TrackingRef 'Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H34 N6 O14 Zn3' _chemical_formula_weight 1090.90 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 Orthorhombic _symmetry_space_group_name_H-M Pcca _symmetry_space_group_name_Hall '-P 2a 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x+1/2, -y, -z+1/2' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x-1/2, y, z-1/2' 'x, -y, z-1/2' _cell_length_a 25.161(3) _cell_length_b 11.253(2) _cell_length_c 18.172(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.000(4) _cell_angle_gamma 90.00 _cell_volume 5145.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2216 _exptl_absorpt_coefficient_mu 1.454 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7037 _exptl_absorpt_correction_T_max 0.7901 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40805 _diffrn_reflns_av_R_equivalents 0.1128 _diffrn_reflns_av_sigmaI/netI 0.1071 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 25.37 _reflns_number_total 4694 _reflns_number_gt 2622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 distance of O2W---H2A was restrained to 0.89+-0.02 \%A. The distance of O1W---H1A was restrained to 0.87+-0.01 \%A. The distance of H1A...H2A was restrained to 2.50+-0.02 \%A. The distance of Zn2...H1A was restrained to 2.50+-0.01 \%A. ; _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^)+(0.0599P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4694 _refine_ls_number_parameters 324 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 0.871 _refine_ls_restrained_S_all 0.872 _refine_ls_shift/su_max 0.003 _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 Zn1 Zn -0.02537(2) 0.37973(4) 0.07359(3) 0.02931(17) Uani 1 1 d . . . Zn2 Zn 0.2500 1.0000 0.29015(4) 0.0317(2) Uani 1 2 d SD . . C1 C 0.0636(2) 0.5636(4) 0.0708(3) 0.0305(11) Uani 1 1 d . . . C2 C 0.0911(2) 0.6023(4) 0.1393(2) 0.0284(11) Uani 1 1 d . . . C3 C 0.0764(2) 0.5506(4) 0.2063(2) 0.0312(12) Uani 1 1 d . . . H3 H 0.0513 0.4899 0.2072 0.037 Uiso 1 1 calc R . . C4 C 0.0989(2) 0.5894(4) 0.2706(3) 0.0347(13) Uani 1 1 d . . . C5 C 0.1369(2) 0.6786(4) 0.2691(3) 0.0371(13) Uani 1 1 d . . . H5 H 0.1520 0.7049 0.3129 0.045 Uiso 1 1 calc R . . C6 C 0.1527(2) 0.7288(4) 0.2031(3) 0.0317(12) Uani 1 1 d . . . C7 C 0.1293(2) 0.6909(4) 0.1385(3) 0.0299(12) Uani 1 1 d . . . H7 H 0.1392 0.7252 0.0940 0.036 Uiso 1 1 calc R . . C8 C 0.1933(2) 0.8273(4) 0.2037(4) 0.0461(14) Uani 1 1 d . . . C9 C 0.0820(3) 0.5362(5) 0.3423(3) 0.0505(16) Uani 1 1 d . . . C10 C 0.0313(2) 0.1442(4) 0.0677(2) 0.0279(11) Uani 1 1 d . . . C11 C 0.0747(2) 0.1849(4) 0.0278(3) 0.0362(13) Uani 1 1 d . . . H11 H 0.0781 0.2645 0.0149 0.043 Uiso 1 1 calc R . . C12 C 0.1128(2) 0.1022(5) 0.0080(3) 0.0461(14) Uani 1 1 d . . . H12 H 0.1430 0.1269 -0.0171 0.055 Uiso 1 1 calc R . . C13 C 0.1063(3) -0.0191(5) 0.0254(3) 0.0510(16) Uani 1 1 d . . . H13 H 0.1325 -0.0727 0.0111 0.061 Uiso 1 1 calc R . . C14 C 0.0632(2) -0.0601(4) 0.0622(3) 0.0414(14) Uani 1 1 d . . . H14 H 0.0589 -0.1406 0.0720 0.050 Uiso 1 1 calc R . . C15 C 0.0256(2) 0.0239(4) 0.0850(2) 0.0295(11) Uani 1 1 d . . . C16 C -0.04081(19) 0.1259(4) 0.1334(2) 0.0266(11) Uani 1 1 d . . . C17 C -0.0871(2) 0.1508(4) 0.1809(3) 0.0299(12) Uani 1 1 d . . . C18 C -0.1355(2) 0.0963(4) 0.1713(3) 0.0365(13) Uani 1 1 d . . . H18 H -0.1402 0.0474 0.1306 0.044 Uiso 1 1 calc R . . C19 C -0.0811(2) 0.2261(4) 0.2416(3) 0.0380(13) Uani 1 1 d . . . H19 H -0.0492 0.2655 0.2498 0.046 Uiso 1 1 calc R . . C20 C -0.1228(2) 0.2406(5) 0.2885(3) 0.0487(15) Uani 1 1 d . . . H20 H -0.1198 0.2908 0.3289 0.058 Uiso 1 1 calc R . . C21 C -0.1696(2) 0.1805(5) 0.2755(3) 0.0495(15) Uani 1 1 d . . . H21 H -0.1975 0.1897 0.3086 0.059 Uiso 1 1 calc R . . C22 C -0.0407(2) -0.0962(4) 0.1588(3) 0.0344(13) Uani 1 1 d . . . H22A H -0.0243 -0.1635 0.1345 0.041 Uiso 1 1 calc R . . H22B H -0.0788 -0.1015 0.1510 0.041 Uiso 1 1 calc R . . C23 C -0.0292(2) -0.1028(4) 0.2411(2) 0.0345(12) Uani 1 1 d . . . H23A H -0.0458 -0.0356 0.2653 0.041 Uiso 1 1 calc R . . H23B H -0.0451 -0.1746 0.2608 0.041 Uiso 1 1 calc R . . N1 N -0.01081(16) 0.2062(3) 0.09902(19) 0.0269(10) Uani 1 1 d . . . N2 N -0.02083(17) 0.0144(3) 0.12540(19) 0.0289(9) Uani 1 1 d . . . N3 N -0.17639(18) 0.1104(4) 0.2182(2) 0.0411(11) Uani 1 1 d . . . O1 O 0.04409(14) 0.4612(3) 0.06675(18) 0.0393(9) Uani 1 1 d . . . O2 O 0.06125(15) 0.6394(3) 0.01967(17) 0.0422(10) Uani 1 1 d . . . O3 O 0.20621(16) 0.8629(3) 0.2670(2) 0.0545(11) Uani 1 1 d . . . O4 O 0.21173(19) 0.8649(4) 0.1450(3) 0.0755(14) Uani 1 1 d . . . O5 O 0.0962(3) 0.5796(5) 0.4008(3) 0.132(3) Uani 1 1 d . . . O6 O 0.05223(17) 0.4476(3) 0.33804(19) 0.0485(11) Uani 1 1 d . . . O1W O 0.2500 1.0000 0.4014(3) 0.0682(17) Uani 1 2 d SD . . H1A H 0.2322(18) 0.941(3) 0.4201(7) 0.102 Uiso 1 1 d D . . O2W O 0.2643(4) 0.8198(7) 0.4977(4) 0.060(3) Uani 0.50 1 d PD . . H2A H 0.2913(19) 0.791(6) 0.479(3) 0.089 Uiso 1 1 d 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 0.0389(4) 0.0241(3) 0.0249(3) -0.0012(2) -0.0022(3) -0.0026(3) Zn2 0.0278(5) 0.0328(4) 0.0347(4) 0.000 0.000 -0.0090(4) C1 0.029(3) 0.032(3) 0.031(3) -0.003(2) 0.003(2) -0.001(2) C2 0.029(3) 0.023(2) 0.033(3) 0.001(2) -0.004(2) -0.001(2) C3 0.037(3) 0.023(2) 0.034(3) 0.000(2) 0.000(3) -0.005(2) C4 0.045(4) 0.028(2) 0.031(3) 0.004(2) 0.000(2) -0.005(2) C5 0.041(4) 0.038(3) 0.033(3) -0.005(2) -0.007(2) -0.002(2) C6 0.029(3) 0.025(2) 0.042(3) 0.000(2) -0.007(2) -0.002(2) C7 0.031(3) 0.027(2) 0.032(3) 0.0082(19) -0.001(2) -0.003(2) C8 0.035(4) 0.041(3) 0.063(4) 0.009(3) -0.020(3) -0.002(3) C9 0.062(5) 0.054(4) 0.035(3) 0.002(3) 0.000(3) -0.008(3) C10 0.025(3) 0.032(2) 0.026(2) -0.003(2) -0.003(2) 0.001(2) C11 0.037(4) 0.038(3) 0.034(3) -0.002(2) 0.004(3) -0.001(3) C12 0.042(4) 0.062(4) 0.034(3) -0.003(3) 0.009(3) 0.000(3) C13 0.057(5) 0.056(4) 0.040(3) -0.006(3) 0.007(3) 0.021(3) C14 0.052(4) 0.032(3) 0.040(3) 0.001(2) -0.003(3) 0.012(3) C15 0.036(3) 0.028(2) 0.025(3) -0.0003(18) -0.006(2) 0.003(2) C16 0.023(3) 0.028(2) 0.029(2) -0.002(2) -0.006(2) 0.002(2) C17 0.027(3) 0.029(2) 0.034(3) 0.005(2) -0.004(2) 0.002(2) C18 0.033(4) 0.041(3) 0.036(3) -0.004(2) 0.001(3) 0.000(3) C19 0.033(4) 0.043(3) 0.038(3) -0.002(2) 0.003(3) -0.002(2) C20 0.051(4) 0.054(3) 0.042(3) -0.013(3) 0.001(3) 0.000(3) C21 0.035(4) 0.067(3) 0.047(4) -0.017(3) 0.009(3) -0.005(3) C22 0.041(4) 0.025(2) 0.038(3) 0.003(2) -0.004(2) -0.004(2) C23 0.043(3) 0.025(2) 0.036(3) 0.005(2) -0.003(3) -0.006(2) N1 0.031(3) 0.0236(18) 0.026(2) 0.0002(16) -0.0008(18) -0.0017(17) N2 0.031(3) 0.027(2) 0.028(2) 0.0032(16) -0.0015(19) 0.0038(19) N3 0.037(3) 0.046(2) 0.041(3) -0.004(2) 0.006(2) 0.000(2) O1 0.045(3) 0.0292(17) 0.044(2) -0.0043(15) -0.0007(18) -0.0138(15) O2 0.063(3) 0.0338(18) 0.0297(19) 0.0048(15) -0.0160(17) -0.0075(17) O3 0.045(3) 0.044(2) 0.075(3) -0.0118(19) -0.016(2) -0.0154(19) O4 0.068(3) 0.083(3) 0.075(3) 0.028(2) -0.017(3) -0.044(3) O5 0.214(8) 0.144(5) 0.037(3) -0.004(3) -0.006(3) -0.109(5) O6 0.069(3) 0.0409(19) 0.036(2) 0.0089(16) 0.0034(19) -0.017(2) O1W 0.077(5) 0.089(4) 0.038(3) 0.000 0.000 0.003(4) O2W 0.075(8) 0.070(5) 0.034(4) 0.030(4) -0.012(4) 0.009(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 Zn1 O6 1.902(3) 4 ? Zn1 O2 1.932(3) 5_565 ? Zn1 O1 1.978(3) . ? Zn1 N1 2.040(3) . ? Zn2 O3 1.942(3) . ? Zn2 O3 1.942(3) 2_575 ? Zn2 O1W 2.021(5) . ? Zn2 N3 2.235(4) 4_565 ? Zn2 N3 2.235(4) 3_565 ? C1 O1 1.254(5) . ? C1 O2 1.263(5) . ? C1 C2 1.489(6) . ? C2 C7 1.384(6) . ? C2 C3 1.399(6) . ? C3 C4 1.370(6) . ? C3 H3 0.9300 . ? C4 C5 1.387(7) . ? C4 C9 1.496(7) . ? C5 C6 1.383(6) . ? C5 H5 0.9300 . ? C6 C7 1.381(6) . ? C6 C8 1.509(7) . ? C7 H7 0.9300 . ? C8 O4 1.237(7) . ? C8 O3 1.260(6) . ? C9 O5 1.223(7) . ? C9 O6 1.249(6) . ? C10 C11 1.388(7) . ? C10 N1 1.390(6) . ? C10 C15 1.398(6) . ? C11 C12 1.383(7) . ? C11 H11 0.9300 . ? C12 C13 1.410(7) . ? C12 H12 0.9300 . ? C13 C14 1.354(8) . ? C13 H13 0.9300 . ? C14 C15 1.400(7) . ? C14 H14 0.9300 . ? C15 N2 1.384(6) . ? C16 N1 1.333(6) . ? C16 N2 1.360(5) . ? C16 C17 1.476(7) . ? C17 C18 1.376(7) . ? C17 C19 1.399(6) . ? C18 N3 1.344(6) . ? C18 H18 0.9300 . ? C19 C20 1.362(7) . ? C19 H19 0.9300 . ? C20 C21 1.378(8) . ? C20 H20 0.9300 . ? C21 N3 1.319(6) . ? C21 H21 0.9300 . ? C22 N2 1.471(5) . ? C22 C23 1.526(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C23 1.502(10) 4 ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? N3 Zn2 2.235(4) 3_465 ? O2 Zn1 1.932(3) 5_565 ? O6 Zn1 1.902(3) 4 ? O1W H1A 0.869(10) . ? O2W H2A 0.83(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 O6 Zn1 O2 128.26(17) 4 5_565 ? O6 Zn1 O1 100.41(16) 4 . ? O2 Zn1 O1 114.17(15) 5_565 . ? O6 Zn1 N1 104.90(15) 4 . ? O2 Zn1 N1 100.13(13) 5_565 . ? O1 Zn1 N1 107.42(15) . . ? O3 Zn2 O3 154.9(2) . 2_575 ? O3 Zn2 O1W 102.53(12) . . ? O3 Zn2 O1W 102.53(12) 2_575 . ? O3 Zn2 N3 87.53(16) . 4_565 ? O3 Zn2 N3 90.79(16) 2_575 4_565 ? O1W Zn2 N3 93.88(11) . 4_565 ? O3 Zn2 N3 90.79(16) . 3_565 ? O3 Zn2 N3 87.53(16) 2_575 3_565 ? O1W Zn2 N3 93.88(11) . 3_565 ? N3 Zn2 N3 172.2(2) 4_565 3_565 ? O1 C1 O2 124.0(4) . . ? O1 C1 C2 120.0(4) . . ? O2 C1 C2 116.0(4) . . ? C7 C2 C3 119.5(4) . . ? C7 C2 C1 121.6(4) . . ? C3 C2 C1 118.8(4) . . ? C4 C3 C2 120.1(4) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.9(4) . . ? C3 C4 C9 119.9(4) . . ? C5 C4 C9 120.2(4) . . ? C6 C5 C4 120.7(4) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 119.3(4) . . ? C7 C6 C8 121.4(5) . . ? C5 C6 C8 119.3(5) . . ? C6 C7 C2 120.6(4) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? O4 C8 O3 125.6(5) . . ? O4 C8 C6 119.9(5) . . ? O3 C8 C6 114.4(5) . . ? O5 C9 O6 123.2(5) . . ? O5 C9 C4 121.0(5) . . ? O6 C9 C4 115.8(5) . . ? C11 C10 N1 130.4(4) . . ? C11 C10 C15 121.1(4) . . ? N1 C10 C15 108.4(4) . . ? C12 C11 C10 117.3(4) . . ? C12 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? C11 C12 C13 120.8(5) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 122.2(5) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 117.2(5) . . ? C13 C14 H14 121.4 . . ? C15 C14 H14 121.4 . . ? N2 C15 C10 106.3(4) . . ? N2 C15 C14 132.5(4) . . ? C10 C15 C14 121.2(5) . . ? N1 C16 N2 111.5(4) . . ? N1 C16 C17 126.3(4) . . ? N2 C16 C17 122.0(4) . . ? C18 C17 C19 117.7(5) . . ? C18 C17 C16 122.7(4) . . ? C19 C17 C16 119.4(5) . . ? N3 C18 C17 123.1(5) . . ? N3 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? C20 C19 C17 118.9(5) . . ? C20 C19 H19 120.5 . . ? C17 C19 H19 120.5 . . ? C19 C20 C21 119.5(5) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? N3 C21 C20 122.7(5) . . ? N3 C21 H21 118.7 . . ? C20 C21 H21 118.7 . . ? N2 C22 C23 112.4(4) . . ? N2 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? N2 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? C23 C23 C22 113.3(5) 4 . ? C23 C23 H23A 108.9 4 . ? C22 C23 H23A 108.9 . . ? C23 C23 H23B 108.9 4 . ? C22 C23 H23B 108.9 . . ? H23A C23 H23B 107.7 . . ? C16 N1 C10 106.5(3) . . ? C16 N1 Zn1 130.8(3) . . ? C10 N1 Zn1 121.6(3) . . ? C16 N2 C15 107.3(4) . . ? C16 N2 C22 127.6(4) . . ? C15 N2 C22 124.8(4) . . ? C21 N3 C18 118.2(5) . . ? C21 N3 Zn2 119.6(4) . 3_465 ? C18 N3 Zn2 121.7(3) . 3_465 ? C1 O1 Zn1 140.1(3) . . ? C1 O2 Zn1 126.3(3) . 5_565 ? C8 O3 Zn2 126.6(4) . . ? C9 O6 Zn1 118.7(3) . 4 ? Zn2 O1W H1A 113.1(12) . . ? 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 O1 C1 C2 C7 155.3(5) . . . . ? O2 C1 C2 C7 -25.1(7) . . . . ? O1 C1 C2 C3 -27.2(7) . . . . ? O2 C1 C2 C3 152.3(4) . . . . ? C7 C2 C3 C4 1.3(7) . . . . ? C1 C2 C3 C4 -176.2(4) . . . . ? C2 C3 C4 C5 -1.1(7) . . . . ? C2 C3 C4 C9 178.3(5) . . . . ? C3 C4 C5 C6 -0.3(8) . . . . ? C9 C4 C5 C6 -179.7(5) . . . . ? C4 C5 C6 C7 1.4(7) . . . . ? C4 C5 C6 C8 178.8(4) . . . . ? C5 C6 C7 C2 -1.1(7) . . . . ? C8 C6 C7 C2 -178.4(4) . . . . ? C3 C2 C7 C6 -0.2(7) . . . . ? C1 C2 C7 C6 177.3(4) . . . . ? C7 C6 C8 O4 -9.9(8) . . . . ? C5 C6 C8 O4 172.8(5) . . . . ? C7 C6 C8 O3 171.3(5) . . . . ? C5 C6 C8 O3 -6.0(7) . . . . ? C3 C4 C9 O5 -170.4(7) . . . . ? C5 C4 C9 O5 9.0(9) . . . . ? C3 C4 C9 O6 8.5(8) . . . . ? C5 C4 C9 O6 -172.1(5) . . . . ? N1 C10 C11 C12 175.3(5) . . . . ? C15 C10 C11 C12 -2.0(7) . . . . ? C10 C11 C12 C13 2.4(7) . . . . ? C11 C12 C13 C14 -0.4(8) . . . . ? C12 C13 C14 C15 -2.1(8) . . . . ? C11 C10 C15 N2 179.1(4) . . . . ? N1 C10 C15 N2 1.3(5) . . . . ? C11 C10 C15 C14 -0.5(7) . . . . ? N1 C10 C15 C14 -178.3(4) . . . . ? C13 C14 C15 N2 -177.0(5) . . . . ? C13 C14 C15 C10 2.5(7) . . . . ? N1 C16 C17 C18 128.8(5) . . . . ? N2 C16 C17 C18 -57.5(6) . . . . ? N1 C16 C17 C19 -56.0(6) . . . . ? N2 C16 C17 C19 117.7(5) . . . . ? C19 C17 C18 N3 -1.3(7) . . . . ? C16 C17 C18 N3 173.9(4) . . . . ? C18 C17 C19 C20 0.8(7) . . . . ? C16 C17 C19 C20 -174.6(4) . . . . ? C17 C19 C20 C21 0.5(8) . . . . ? C19 C20 C21 N3 -1.5(9) . . . . ? N2 C22 C23 C23 -62.3(4) . . . 4 ? N2 C16 N1 C10 -0.7(5) . . . . ? C17 C16 N1 C10 173.5(4) . . . . ? N2 C16 N1 Zn1 167.0(3) . . . . ? C17 C16 N1 Zn1 -18.7(7) . . . . ? C11 C10 N1 C16 -177.9(5) . . . . ? C15 C10 N1 C16 -0.4(5) . . . . ? C11 C10 N1 Zn1 12.9(7) . . . . ? C15 C10 N1 Zn1 -169.5(3) . . . . ? O6 Zn1 N1 C16 47.7(4) 4 . . . ? O2 Zn1 N1 C16 -86.6(4) 5_565 . . . ? O1 Zn1 N1 C16 153.9(4) . . . . ? O6 Zn1 N1 C10 -146.1(3) 4 . . . ? O2 Zn1 N1 C10 79.6(4) 5_565 . . . ? O1 Zn1 N1 C10 -39.9(4) . . . . ? N1 C16 N2 C15 1.6(5) . . . . ? C17 C16 N2 C15 -173.0(4) . . . . ? N1 C16 N2 C22 176.0(4) . . . . ? C17 C16 N2 C22 1.4(7) . . . . ? C10 C15 N2 C16 -1.7(5) . . . . ? C14 C15 N2 C16 177.8(5) . . . . ? C10 C15 N2 C22 -176.3(4) . . . . ? C14 C15 N2 C22 3.2(8) . . . . ? C23 C22 N2 C16 -72.4(6) . . . . ? C23 C22 N2 C15 101.1(5) . . . . ? C20 C21 N3 C18 1.0(8) . . . . ? C20 C21 N3 Zn2 172.5(4) . . . 3_465 ? C17 C18 N3 C21 0.4(7) . . . . ? C17 C18 N3 Zn2 -170.9(4) . . . 3_465 ? O2 C1 O1 Zn1 -78.0(7) . . . . ? C2 C1 O1 Zn1 101.5(6) . . . . ? O6 Zn1 O1 C1 -48.4(5) 4 . . . ? O2 Zn1 O1 C1 92.2(5) 5_565 . . . ? N1 Zn1 O1 C1 -157.8(5) . . . . ? O1 C1 O2 Zn1 2.9(7) . . . 5_565 ? C2 C1 O2 Zn1 -176.6(3) . . . 5_565 ? O4 C8 O3 Zn2 9.6(9) . . . . ? C6 C8 O3 Zn2 -171.7(3) . . . . ? O3 Zn2 O3 C8 -1.8(4) 2_575 . . . ? O1W Zn2 O3 C8 178.2(4) . . . . ? N3 Zn2 O3 C8 84.8(5) 4_565 . . . ? N3 Zn2 O3 C8 -87.6(5) 3_565 . . . ? O5 C9 O6 Zn1 2.5(9) . . . 4 ? C4 C9 O6 Zn1 -176.4(4) . . . 4 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1A O2W 0.869(10) 2.12(4) 2.703(7) 124(4) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.993 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.090 data_5 _database_code_depnum_ccdc_archive 'CCDC 912026' #TrackingRef 'Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 Cd N3 O5' _chemical_formula_weight 516.79 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.176(5) _cell_length_b 10.783(2) _cell_length_c 11.423(3) _cell_angle_alpha 80.530(6) _cell_angle_beta 67.186(7) _cell_angle_gamma 78.205(2) _cell_volume 1015.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 518 _exptl_absorpt_coefficient_mu 1.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7601 _exptl_absorpt_correction_T_max 0.8244 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7443 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.1554 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 29.23 _reflns_number_total 4618 _reflns_number_gt 2591 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 distances of O1W---H1A and O1W---H1B were restrained to 0.87+-0.02 \%A. ; _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4618 _refine_ls_number_parameters 286 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0550 _refine_ls_wR_factor_gt 0.0518 _refine_ls_goodness_of_fit_ref 0.773 _refine_ls_restrained_S_all 0.773 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.50900(4) 0.40855(3) 0.22213(3) 0.03258(10) Uani 1 1 d . . . C1 C 0.3216(6) 0.2856(3) 0.1507(4) 0.0349(11) Uani 1 1 d . . . C2 C 0.2130(5) 0.2530(3) 0.0958(4) 0.0315(10) Uani 1 1 d . . . C3 C 0.1319(5) 0.1486(3) 0.1550(4) 0.0433(12) Uani 1 1 d . . . H3 H 0.1516 0.1007 0.2243 0.052 Uiso 1 1 calc R . . C4 C 0.0237(6) 0.1149(4) 0.1132(4) 0.0522(13) Uani 1 1 d . . . H4 H -0.0266 0.0443 0.1522 0.063 Uiso 1 1 calc R . . C5 C -0.0078(5) 0.1888(4) 0.0122(4) 0.0513(12) Uani 1 1 d . . . H5 H -0.0837 0.1704 -0.0149 0.062 Uiso 1 1 calc R . . C6 C 0.0731(5) 0.2899(4) -0.0483(4) 0.0436(11) Uani 1 1 d . . . H6 H 0.0514 0.3382 -0.1166 0.052 Uiso 1 1 calc R . . C7 C 0.1853(5) 0.3213(3) -0.0103(3) 0.0310(10) Uani 1 1 d . . . C8 C 0.2751(5) 0.4279(4) -0.0853(4) 0.0371(11) Uani 1 1 d . . . C9 C 0.6415(4) 0.1091(3) 0.3041(4) 0.0297(10) Uani 1 1 d . . . C10 C 0.6042(5) 0.0520(3) 0.2226(4) 0.0372(11) Uani 1 1 d . . . H10 H 0.5711 0.1001 0.1595 0.045 Uiso 1 1 calc R . . C11 C 0.6172(4) -0.0789(3) 0.2373(4) 0.0424(12) Uani 1 1 d . . . H11 H 0.5952 -0.1203 0.1821 0.051 Uiso 1 1 calc R . . C12 C 0.6629(5) -0.1489(3) 0.3340(4) 0.0441(12) Uani 1 1 d . . . H12 H 0.6686 -0.2369 0.3432 0.053 Uiso 1 1 calc R . . C13 C 0.6997(5) -0.0942(3) 0.4159(4) 0.0399(12) Uani 1 1 d . . . H13 H 0.7292 -0.1424 0.4808 0.048 Uiso 1 1 calc R . . C14 C 0.6913(4) 0.0365(3) 0.3979(3) 0.0286(10) Uani 1 1 d . . . C15 C 0.6337(5) 0.4107(3) 0.5445(4) 0.0335(10) Uani 1 1 d . . . H15 H 0.5445 0.3742 0.5984 0.040 Uiso 1 1 calc R . . C16 C 0.7304(5) 0.3543(3) 0.4340(3) 0.0270(10) Uani 1 1 d . . . C17 C 0.8629(5) 0.4087(3) 0.3534(4) 0.0371(11) Uani 1 1 d . . . H17 H 0.9297 0.3752 0.2771 0.045 Uiso 1 1 calc R . . C18 C 0.8935(5) 0.5145(3) 0.3893(4) 0.0408(11) Uani 1 1 d . . . H18 H 0.9823 0.5526 0.3378 0.049 Uiso 1 1 calc R . . C19 C 0.7914(5) 0.5621(3) 0.5012(4) 0.0350(11) Uani 1 1 d . . . H19 H 0.8147 0.6322 0.5247 0.042 Uiso 1 1 calc R . . C20 C 0.6973(4) 0.2402(3) 0.4008(3) 0.0270(10) Uani 1 1 d . . . C21 C 0.7800(4) 0.0898(3) 0.5668(3) 0.0359(11) Uani 1 1 d . . . H21A H 0.7348 0.0161 0.6182 0.043 Uiso 1 1 calc R . . H21B H 0.7381 0.1604 0.6195 0.043 Uiso 1 1 calc R . . C22 C 0.9592(4) 0.0623(3) 0.5301(4) 0.0370(11) Uani 1 1 d . . . H22A H 0.9834 0.0609 0.6058 0.044 Uiso 1 1 calc R . . H22B H 1.0052 0.1317 0.4705 0.044 Uiso 1 1 calc R . . N1 N 0.6444(4) 0.2368(3) 0.3092(3) 0.0308(8) Uani 1 1 d . . . N2 N 0.7259(3) 0.1209(3) 0.4589(3) 0.0306(8) Uani 1 1 d . . . N3 N 0.6601(4) 0.5140(3) 0.5789(3) 0.0317(8) Uani 1 1 d . . . O1 O 0.2763(4) 0.2873(3) 0.2676(3) 0.0574(9) Uani 1 1 d . . . O2 O 0.4573(3) 0.3117(2) 0.0763(3) 0.0435(7) Uani 1 1 d . . . O3 O 0.2717(3) 0.5220(2) -0.0331(3) 0.0449(8) Uani 1 1 d . . . O4 O 0.3519(4) 0.4192(2) -0.2012(3) 0.0542(9) Uani 1 1 d . . . O1W O 0.3329(5) 0.5863(3) 0.1607(3) 0.0619(10) Uani 1 1 d D . . H1B H 0.397(5) 0.640(4) 0.121(5) 0.093 Uiso 1 1 d D . . H1A H 0.282(5) 0.554(4) 0.126(5) 0.093 Uiso 1 1 d 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 Cd1 0.0436(2) 0.02739(15) 0.03181(17) -0.00217(11) -0.01937(14) -0.00583(12) C1 0.043(3) 0.026(2) 0.040(3) -0.0070(19) -0.019(3) -0.004(2) C2 0.037(3) 0.026(2) 0.033(2) -0.0075(17) -0.011(2) -0.0061(18) C3 0.054(3) 0.039(2) 0.035(3) 0.0010(19) -0.015(2) -0.010(2) C4 0.051(3) 0.047(3) 0.057(3) -0.010(2) -0.009(3) -0.021(2) C5 0.042(3) 0.064(3) 0.059(3) -0.009(2) -0.023(2) -0.020(2) C6 0.038(3) 0.053(3) 0.042(3) -0.001(2) -0.016(2) -0.012(2) C7 0.029(3) 0.033(2) 0.028(2) -0.0084(18) -0.005(2) -0.0062(19) C8 0.041(3) 0.031(2) 0.045(3) 0.001(2) -0.025(2) -0.004(2) C9 0.029(2) 0.028(2) 0.035(2) -0.0124(17) -0.013(2) -0.0001(18) C10 0.034(3) 0.036(2) 0.045(3) -0.0136(19) -0.017(2) 0.0005(19) C11 0.035(3) 0.034(2) 0.063(3) -0.018(2) -0.020(2) -0.001(2) C12 0.036(3) 0.023(2) 0.072(4) -0.007(2) -0.017(3) -0.0053(19) C13 0.044(3) 0.024(2) 0.054(3) 0.0025(19) -0.023(2) -0.0028(19) C14 0.028(2) 0.026(2) 0.033(2) -0.0012(17) -0.0131(19) -0.0031(17) C15 0.037(3) 0.030(2) 0.040(3) 0.0031(18) -0.020(2) -0.0112(19) C16 0.037(3) 0.0192(19) 0.025(2) -0.0031(16) -0.015(2) 0.0029(18) C17 0.045(3) 0.033(2) 0.034(2) -0.0126(18) -0.012(2) -0.002(2) C18 0.039(3) 0.042(2) 0.039(3) 0.004(2) -0.012(2) -0.013(2) C19 0.051(3) 0.022(2) 0.040(3) -0.0013(18) -0.025(2) -0.007(2) C20 0.031(2) 0.022(2) 0.027(2) -0.0052(16) -0.0095(19) 0.0004(17) C21 0.040(3) 0.037(2) 0.030(2) 0.0023(17) -0.017(2) 0.0001(19) C22 0.041(3) 0.037(2) 0.036(3) 0.0033(18) -0.020(2) -0.006(2) N1 0.039(2) 0.0245(17) 0.032(2) -0.0033(13) -0.0171(17) -0.0046(15) N2 0.032(2) 0.0270(17) 0.0330(19) -0.0005(14) -0.0157(16) 0.0007(15) N3 0.040(2) 0.0263(17) 0.034(2) -0.0035(14) -0.0197(17) -0.0035(16) O1 0.065(2) 0.076(2) 0.040(2) -0.0230(16) -0.0244(18) -0.0045(17) O2 0.048(2) 0.0483(16) 0.0464(19) 0.0007(13) -0.0265(16) -0.0187(14) O3 0.059(2) 0.0324(15) 0.053(2) -0.0023(14) -0.0295(16) -0.0112(14) O4 0.069(2) 0.0573(18) 0.0367(19) -0.0039(14) -0.0095(17) -0.0300(16) O1W 0.089(3) 0.048(2) 0.063(2) -0.0048(16) -0.049(2) 0.0001(17) _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 N1 2.318(3) . ? Cd1 O2 2.341(3) . ? Cd1 N3 2.373(3) 2_666 ? Cd1 O4 2.393(3) 2_665 ? Cd1 O1W 2.439(3) . ? Cd1 O3 2.447(3) 2_665 ? Cd1 O1 2.568(3) . ? Cd1 C8 2.757(4) 2_665 ? C1 O1 1.237(4) . ? C1 O2 1.263(5) . ? C1 C2 1.486(6) . ? C2 C7 1.395(5) . ? C2 C3 1.408(5) . ? C3 C4 1.385(6) . ? C3 H3 0.9300 . ? C4 C5 1.382(6) . ? C4 H4 0.9300 . ? C5 C6 1.379(5) . ? C5 H5 0.9300 . ? C6 C7 1.378(6) . ? C6 H6 0.9300 . ? C7 C8 1.500(5) . ? C8 O4 1.245(4) . ? C8 O3 1.248(4) . ? C8 Cd1 2.757(4) 2_665 ? C9 C10 1.373(5) . ? C9 C14 1.388(5) . ? C9 N1 1.394(4) . ? C10 C11 1.379(5) . ? C10 H10 0.9300 . ? C11 C12 1.387(5) . ? C11 H11 0.9300 . ? C12 C13 1.358(5) . ? C12 H12 0.9300 . ? C13 C14 1.381(5) . ? C13 H13 0.9300 . ? C14 N2 1.383(5) . ? C15 N3 1.335(4) . ? C15 C16 1.384(4) . ? C15 H15 0.9300 . ? C16 C17 1.384(5) . ? C16 C20 1.465(5) . ? C17 C18 1.387(5) . ? C17 H17 0.9300 . ? C18 C19 1.366(5) . ? C18 H18 0.9300 . ? C19 N3 1.336(5) . ? C19 H19 0.9300 . ? C20 N1 1.321(5) . ? C20 N2 1.371(4) . ? C21 N2 1.465(4) . ? C21 C22 1.508(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C22 1.527(6) 2_756 ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? N3 Cd1 2.373(3) 2_666 ? O3 Cd1 2.447(3) 2_665 ? O4 Cd1 2.393(3) 2_665 ? O1W H1B 0.860(19) . ? O1W H1A 0.863(19) . ? 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 Cd1 O2 101.13(10) . . ? N1 Cd1 N3 94.92(10) . 2_666 ? O2 Cd1 N3 131.89(12) . 2_666 ? N1 Cd1 O4 104.07(11) . 2_665 ? O2 Cd1 O4 133.41(10) . 2_665 ? N3 Cd1 O4 84.06(11) 2_666 2_665 ? N1 Cd1 O1W 171.42(13) . . ? O2 Cd1 O1W 81.32(10) . . ? N3 Cd1 O1W 77.56(11) 2_666 . ? O4 Cd1 O1W 79.49(12) 2_665 . ? N1 Cd1 O3 101.09(10) . 2_665 ? O2 Cd1 O3 83.77(10) . 2_665 ? N3 Cd1 O3 136.93(11) 2_666 2_665 ? O4 Cd1 O3 53.39(9) 2_665 2_665 ? O1W Cd1 O3 87.31(11) . 2_665 ? N1 Cd1 O1 91.78(11) . . ? O2 Cd1 O1 52.63(9) . . ? N3 Cd1 O1 82.09(11) 2_666 . ? O4 Cd1 O1 159.76(8) 2_665 . ? O1W Cd1 O1 83.16(11) . . ? O3 Cd1 O1 136.26(10) 2_665 . ? N1 Cd1 C8 107.15(12) . 2_665 ? O2 Cd1 C8 107.86(12) . 2_665 ? N3 Cd1 C8 110.06(13) 2_666 2_665 ? O4 Cd1 C8 26.80(10) 2_665 2_665 ? O1W Cd1 C8 79.61(13) . 2_665 ? O3 Cd1 C8 26.91(10) 2_665 2_665 ? O1 Cd1 C8 155.99(11) . 2_665 ? O1 C1 O2 121.9(4) . . ? O1 C1 C2 119.2(4) . . ? O2 C1 C2 118.9(4) . . ? C7 C2 C3 118.0(4) . . ? C7 C2 C1 123.6(4) . . ? C3 C2 C1 118.3(4) . . ? C4 C3 C2 122.1(4) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C5 C4 C3 118.5(4) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C6 C5 C4 120.0(5) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 121.9(4) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C2 119.4(4) . . ? C6 C7 C8 118.8(4) . . ? C2 C7 C8 121.8(4) . . ? O4 C8 O3 121.5(4) . . ? O4 C8 C7 117.5(4) . . ? O3 C8 C7 121.0(4) . . ? O4 C8 Cd1 60.1(2) . 2_665 ? O3 C8 Cd1 62.6(2) . 2_665 ? C7 C8 Cd1 169.0(3) . 2_665 ? C10 C9 C14 120.6(3) . . ? C10 C9 N1 130.6(3) . . ? C14 C9 N1 108.8(4) . . ? C9 C10 C11 118.1(4) . . ? C9 C10 H10 121.0 . . ? C11 C10 H10 121.0 . . ? C10 C11 C12 120.2(4) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 122.7(4) . . ? C13 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? C12 C13 C14 116.7(4) . . ? C12 C13 H13 121.6 . . ? C14 C13 H13 121.6 . . ? C13 C14 N2 132.0(4) . . ? C13 C14 C9 121.7(4) . . ? N2 C14 C9 106.3(3) . . ? N3 C15 C16 124.3(4) . . ? N3 C15 H15 117.9 . . ? C16 C15 H15 117.9 . . ? C17 C16 C15 118.0(4) . . ? C17 C16 C20 119.7(3) . . ? C15 C16 C20 122.3(4) . . ? C16 C17 C18 118.3(4) . . ? C16 C17 H17 120.9 . . ? C18 C17 H17 120.9 . . ? C19 C18 C17 119.2(4) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? N3 C19 C18 123.8(4) . . ? N3 C19 H19 118.1 . . ? C18 C19 H19 118.1 . . ? N1 C20 N2 111.5(3) . . ? N1 C20 C16 125.4(3) . . ? N2 C20 C16 123.0(3) . . ? N2 C21 C22 114.7(3) . . ? N2 C21 H21A 108.6 . . ? C22 C21 H21A 108.6 . . ? N2 C21 H21B 108.6 . . ? C22 C21 H21B 108.6 . . ? H21A C21 H21B 107.6 . . ? C21 C22 C22 115.4(4) . 2_756 ? C21 C22 H22A 108.4 . . ? C22 C22 H22A 108.4 2_756 . ? C21 C22 H22B 108.4 . . ? C22 C22 H22B 108.4 2_756 . ? H22A C22 H22B 107.5 . . ? C20 N1 C9 106.4(3) . . ? C20 N1 Cd1 125.6(2) . . ? C9 N1 Cd1 125.4(3) . . ? C20 N2 C14 107.0(3) . . ? C20 N2 C21 126.2(3) . . ? C14 N2 C21 126.8(3) . . ? C15 N3 C19 116.4(3) . . ? C15 N3 Cd1 120.0(3) . 2_666 ? C19 N3 Cd1 123.4(3) . 2_666 ? C1 O1 Cd1 86.7(3) . . ? C1 O2 Cd1 96.6(3) . . ? C8 O3 Cd1 90.5(2) . 2_665 ? C8 O4 Cd1 93.1(3) . 2_665 ? Cd1 O1W H1B 102(4) . . ? Cd1 O1W H1A 106(3) . . ? H1B O1W H1A 124(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 O1 C1 C2 C7 134.2(4) . . . . ? O2 C1 C2 C7 -45.3(5) . . . . ? O1 C1 C2 C3 -44.9(5) . . . . ? O2 C1 C2 C3 135.6(4) . . . . ? C7 C2 C3 C4 -1.9(6) . . . . ? C1 C2 C3 C4 177.3(4) . . . . ? C2 C3 C4 C5 -1.7(6) . . . . ? C3 C4 C5 C6 2.9(6) . . . . ? C4 C5 C6 C7 -0.6(6) . . . . ? C5 C6 C7 C2 -3.0(6) . . . . ? C5 C6 C7 C8 176.6(4) . . . . ? C3 C2 C7 C6 4.2(5) . . . . ? C1 C2 C7 C6 -175.0(3) . . . . ? C3 C2 C7 C8 -175.5(3) . . . . ? C1 C2 C7 C8 5.4(5) . . . . ? C6 C7 C8 O4 -57.1(5) . . . . ? C2 C7 C8 O4 122.5(4) . . . . ? C6 C7 C8 O3 122.5(4) . . . . ? C2 C7 C8 O3 -57.9(5) . . . . ? C6 C7 C8 Cd1 -131.4(15) . . . 2_665 ? C2 C7 C8 Cd1 48.3(18) . . . 2_665 ? C14 C9 C10 C11 0.2(6) . . . . ? N1 C9 C10 C11 177.7(3) . . . . ? C9 C10 C11 C12 1.6(6) . . . . ? C10 C11 C12 C13 -1.4(6) . . . . ? C11 C12 C13 C14 -0.6(6) . . . . ? C12 C13 C14 N2 -177.1(4) . . . . ? C12 C13 C14 C9 2.5(6) . . . . ? C10 C9 C14 C13 -2.3(6) . . . . ? N1 C9 C14 C13 179.7(3) . . . . ? C10 C9 C14 N2 177.4(3) . . . . ? N1 C9 C14 N2 -0.7(4) . . . . ? N3 C15 C16 C17 -0.3(6) . . . . ? N3 C15 C16 C20 179.5(3) . . . . ? C15 C16 C17 C18 1.6(5) . . . . ? C20 C16 C17 C18 -178.2(3) . . . . ? C16 C17 C18 C19 -0.9(6) . . . . ? C17 C18 C19 N3 -1.2(6) . . . . ? C17 C16 C20 N1 -72.2(5) . . . . ? C15 C16 C20 N1 108.0(4) . . . . ? C17 C16 C20 N2 104.4(4) . . . . ? C15 C16 C20 N2 -75.4(5) . . . . ? N2 C21 C22 C22 -70.2(5) . . . 2_756 ? N2 C20 N1 C9 -1.5(4) . . . . ? C16 C20 N1 C9 175.4(3) . . . . ? N2 C20 N1 Cd1 160.9(2) . . . . ? C16 C20 N1 Cd1 -22.2(5) . . . . ? C10 C9 N1 C20 -176.5(4) . . . . ? C14 C9 N1 C20 1.3(4) . . . . ? C10 C9 N1 Cd1 21.1(5) . . . . ? C14 C9 N1 Cd1 -161.1(2) . . . . ? O2 Cd1 N1 C20 -178.0(3) . . . . ? N3 Cd1 N1 C20 -43.6(3) 2_666 . . . ? O4 Cd1 N1 C20 41.5(3) 2_665 . . . ? O1W Cd1 N1 C20 -72.2(10) . . . . ? O3 Cd1 N1 C20 96.2(3) 2_665 . . . ? O1 Cd1 N1 C20 -125.8(3) . . . . ? C8 Cd1 N1 C20 69.1(3) 2_665 . . . ? O2 Cd1 N1 C9 -18.9(3) . . . . ? N3 Cd1 N1 C9 115.5(3) 2_666 . . . ? O4 Cd1 N1 C9 -159.4(3) 2_665 . . . ? O1W Cd1 N1 C9 87.0(9) . . . . ? O3 Cd1 N1 C9 -104.6(3) 2_665 . . . ? O1 Cd1 N1 C9 33.3(3) . . . . ? C8 Cd1 N1 C9 -131.7(3) 2_665 . . . ? N1 C20 N2 C14 1.1(4) . . . . ? C16 C20 N2 C14 -175.9(3) . . . . ? N1 C20 N2 C21 -177.8(3) . . . . ? C16 C20 N2 C21 5.2(5) . . . . ? C13 C14 N2 C20 179.4(4) . . . . ? C9 C14 N2 C20 -0.2(4) . . . . ? C13 C14 N2 C21 -1.8(6) . . . . ? C9 C14 N2 C21 178.6(3) . . . . ? C22 C21 N2 C20 -90.5(4) . . . . ? C22 C21 N2 C14 90.8(4) . . . . ? C16 C15 N3 C19 -1.7(5) . . . . ? C16 C15 N3 Cd1 -176.3(3) . . . 2_666 ? C18 C19 N3 C15 2.5(5) . . . . ? C18 C19 N3 Cd1 176.9(3) . . . 2_666 ? O2 C1 O1 Cd1 14.5(3) . . . . ? C2 C1 O1 Cd1 -165.0(3) . . . . ? N1 Cd1 O1 C1 -111.0(2) . . . . ? O2 Cd1 O1 C1 -8.31(19) . . . . ? N3 Cd1 O1 C1 154.3(2) 2_666 . . . ? O4 Cd1 O1 C1 107.1(3) 2_665 . . . ? O1W Cd1 O1 C1 76.0(2) . . . . ? O3 Cd1 O1 C1 -2.9(3) 2_665 . . . ? C8 Cd1 O1 C1 31.7(3) 2_665 . . . ? O1 C1 O2 Cd1 -16.1(4) . . . . ? C2 C1 O2 Cd1 163.5(3) . . . . ? N1 Cd1 O2 C1 91.8(2) . . . . ? N3 Cd1 O2 C1 -15.2(2) 2_666 . . . ? O4 Cd1 O2 C1 -146.3(2) 2_665 . . . ? O1W Cd1 O2 C1 -79.8(2) . . . . ? O3 Cd1 O2 C1 -168.0(2) 2_665 . . . ? O1 Cd1 O2 C1 8.18(19) . . . . ? C8 Cd1 O2 C1 -155.9(2) 2_665 . . . ? O4 C8 O3 Cd1 -12.3(4) . . . 2_665 ? C7 C8 O3 Cd1 168.1(3) . . . 2_665 ? O3 C8 O4 Cd1 12.6(4) . . . 2_665 ? C7 C8 O4 Cd1 -167.8(3) . . . 2_665 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1B O2 0.860(19) 2.16(4) 2.844(5) 136(5) 2_665 O1W H1A O3 0.863(19) 1.95(3) 2.706(5) 146(5) . _diffrn_measured_fraction_theta_max 0.835 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.812 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.085 data_6 _database_code_depnum_ccdc_archive 'CCDC 912027' #TrackingRef 'Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 Cd N3 O4' _chemical_formula_weight 498.78 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.424(2) _cell_length_b 9.959(6) _cell_length_c 11.898(5) _cell_angle_alpha 90.723(4) _cell_angle_beta 105.561(8) _cell_angle_gamma 101.282(5) _cell_volume 940.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 1.197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7540 _exptl_absorpt_correction_T_max 0.7957 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17552 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0706 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.40 _diffrn_reflns_theta_max 29.82 _reflns_number_total 4831 _reflns_number_gt 3671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0614P)^2^+0.2936P] 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 4831 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1208 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.82487(4) 0.39410(3) 0.88337(3) 0.02494(12) Uani 1 1 d . . . C1 C 0.9163(6) 0.1480(5) 0.8437(4) 0.0286(10) Uani 1 1 d . . . C2 C 1.0047(6) 0.0375(5) 0.8217(4) 0.0285(10) Uani 1 1 d . . . C3 C 0.9598(6) -0.0948(4) 0.8519(4) 0.0256(9) Uani 1 1 d . . . H3 H 0.8828 -0.1144 0.8957 0.031 Uiso 1 1 calc R . . C4 C 1.0281(6) -0.1996(4) 0.8176(4) 0.0269(9) Uani 1 1 d . . . C5 C 1.1489(7) -0.1700(5) 0.7577(5) 0.0417(12) Uani 1 1 d . . . H5 H 1.1935 -0.2399 0.7332 0.050 Uiso 1 1 calc R . . C6 C 1.2035(9) -0.0346(6) 0.7342(6) 0.0568(17) Uani 1 1 d . . . H6 H 1.2884 -0.0132 0.6970 0.068 Uiso 1 1 calc R . . C7 C 1.1311(8) 0.0682(5) 0.7663(5) 0.0438(13) Uani 1 1 d . . . H7 H 1.1677 0.1584 0.7505 0.053 Uiso 1 1 calc R . . C8 C 0.9682(5) -0.3464(4) 0.8409(4) 0.0272(10) Uani 1 1 d . . . C9 C 0.5617(6) 0.2546(5) 1.0137(5) 0.0362(11) Uani 1 1 d . . . H9 H 0.5600 0.1856 0.9598 0.043 Uiso 1 1 calc R . . C10 C 0.4541(7) 0.2290(5) 1.0827(5) 0.0417(13) Uani 1 1 d . . . H10 H 0.3803 0.1446 1.0756 0.050 Uiso 1 1 calc R . . C11 C 0.4580(6) 0.3318(5) 1.1631(5) 0.0375(11) Uani 1 1 d . . . H11 H 0.3859 0.3170 1.2109 0.045 Uiso 1 1 calc R . . C12 C 0.5688(6) 0.4570(5) 1.1729(4) 0.0287(10) Uani 1 1 d . . . C13 C 0.6740(6) 0.4748(5) 1.0993(4) 0.0276(9) Uani 1 1 d . . . H13 H 0.7491 0.5582 1.1049 0.033 Uiso 1 1 calc R . . C14 C 0.5667(5) 0.5644(5) 1.2595(4) 0.0267(9) Uani 1 1 d . . . C15 C 0.4709(6) 0.6918(5) 1.3638(4) 0.0278(9) Uani 1 1 d . . . C16 C 0.6385(6) 0.6999(5) 1.4211(4) 0.0293(10) Uani 1 1 d . . . C17 C 0.7181(7) 0.7772(6) 1.5272(5) 0.0415(12) Uani 1 1 d . . . H17 H 0.8313 0.7829 1.5655 0.050 Uiso 1 1 calc R . . C18 C 0.6175(8) 0.8440(6) 1.5709(5) 0.0486(14) Uani 1 1 d . . . H18 H 0.6652 0.8989 1.6402 0.058 Uiso 1 1 calc R . . C19 C 0.4470(8) 0.8330(6) 1.5158(5) 0.0454(13) Uani 1 1 d . . . H19 H 0.3831 0.8765 1.5514 0.055 Uiso 1 1 calc R . . C20 C 0.3719(7) 0.7603(6) 1.4114(5) 0.0409(12) Uani 1 1 d . . . H20 H 0.2591 0.7564 1.3732 0.049 Uiso 1 1 calc R . . C21 C 0.8729(6) 0.5985(5) 1.3838(4) 0.0318(10) Uani 1 1 d . . . H21A H 0.9497 0.6863 1.4091 0.038 Uiso 1 1 calc R . . H21B H 0.8955 0.5625 1.3149 0.038 Uiso 1 1 calc R . . C22 C 0.9069(6) 0.5010(5) 1.4796(4) 0.0318(10) Uani 1 1 d . . . H22A H 0.8432 0.4093 1.4507 0.038 Uiso 1 1 calc R . . H22B H 0.8701 0.5294 1.5451 0.038 Uiso 1 1 calc R . . N1 N 0.6707(5) 0.3762(4) 1.0208(3) 0.0272(8) Uani 1 1 d . . . N2 N 0.4277(5) 0.6068(4) 1.2613(3) 0.0288(8) Uani 1 1 d . . . N3 N 0.6994(5) 0.6198(4) 1.3526(3) 0.0282(8) Uani 1 1 d . . . O1 O 0.9760(5) 0.2680(3) 0.8200(3) 0.0379(8) Uani 1 1 d . . . O2 O 0.7911(5) 0.1208(4) 0.8819(3) 0.0436(9) Uani 1 1 d . . . O3 O 0.9317(4) -0.3730(3) 0.9359(3) 0.0360(8) Uani 1 1 d . . . O4 O 0.9540(5) -0.4363(3) 0.7651(3) 0.0435(9) 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 Cd1 0.02416(18) 0.02393(17) 0.02886(19) 0.00023(11) 0.00935(13) 0.00724(12) C1 0.037(3) 0.028(2) 0.023(2) 0.0010(18) 0.008(2) 0.0127(19) C2 0.037(3) 0.026(2) 0.026(2) 0.0017(18) 0.010(2) 0.0112(19) C3 0.030(2) 0.025(2) 0.024(2) 0.0024(17) 0.0092(18) 0.0068(18) C4 0.030(2) 0.022(2) 0.029(2) 0.0035(17) 0.0067(19) 0.0068(18) C5 0.050(3) 0.034(3) 0.053(3) 0.001(2) 0.028(3) 0.017(2) C6 0.072(4) 0.038(3) 0.084(5) 0.010(3) 0.058(4) 0.017(3) C7 0.061(4) 0.025(2) 0.059(4) 0.011(2) 0.035(3) 0.017(2) C8 0.023(2) 0.022(2) 0.036(3) 0.0027(19) 0.0041(19) 0.0097(17) C9 0.034(3) 0.031(2) 0.048(3) -0.005(2) 0.015(2) 0.009(2) C10 0.031(3) 0.033(3) 0.063(4) -0.002(2) 0.023(3) -0.003(2) C11 0.034(3) 0.042(3) 0.044(3) 0.006(2) 0.021(2) 0.011(2) C12 0.025(2) 0.039(3) 0.026(2) 0.0043(19) 0.0061(19) 0.0164(19) C13 0.026(2) 0.029(2) 0.028(2) 0.0028(18) 0.0074(19) 0.0064(18) C14 0.023(2) 0.035(2) 0.026(2) 0.0051(18) 0.0090(18) 0.0116(18) C15 0.028(2) 0.032(2) 0.025(2) 0.0029(18) 0.0078(19) 0.0088(19) C16 0.031(2) 0.034(2) 0.025(2) 0.0025(19) 0.0077(19) 0.013(2) C17 0.041(3) 0.049(3) 0.032(3) -0.001(2) 0.002(2) 0.013(2) C18 0.052(4) 0.055(3) 0.038(3) -0.009(3) 0.007(3) 0.016(3) C19 0.055(4) 0.050(3) 0.041(3) -0.003(2) 0.019(3) 0.026(3) C20 0.037(3) 0.056(3) 0.038(3) 0.004(2) 0.013(2) 0.023(2) C21 0.026(2) 0.041(3) 0.030(3) 0.011(2) 0.007(2) 0.012(2) C22 0.031(3) 0.041(3) 0.026(2) 0.006(2) 0.005(2) 0.015(2) N1 0.026(2) 0.0300(19) 0.028(2) -0.0009(16) 0.0079(16) 0.0105(16) N2 0.027(2) 0.038(2) 0.025(2) 0.0008(16) 0.0085(16) 0.0144(17) N3 0.027(2) 0.036(2) 0.024(2) 0.0041(16) 0.0063(16) 0.0141(16) O1 0.055(2) 0.0229(16) 0.043(2) 0.0044(14) 0.0173(17) 0.0169(15) O2 0.045(2) 0.038(2) 0.056(2) 0.0000(17) 0.0218(19) 0.0180(17) O3 0.0370(19) 0.0327(18) 0.036(2) 0.0055(14) 0.0102(16) 0.0004(14) O4 0.054(2) 0.0264(17) 0.054(2) -0.0017(16) 0.0196(19) 0.0113(16) _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 2.209(3) . ? Cd1 O3 2.329(4) 1_565 ? Cd1 N1 2.334(4) . ? Cd1 N2 2.349(4) 2_667 ? Cd1 O4 2.486(4) 1_565 ? Cd1 O3 2.586(4) 2_757 ? Cd1 C8 2.744(5) 1_565 ? C1 O2 1.242(6) . ? C1 O1 1.269(6) . ? C1 C2 1.500(6) . ? C2 C3 1.378(6) . ? C2 C7 1.384(7) . ? C3 C4 1.392(6) . ? C4 C5 1.381(7) . ? C4 C8 1.505(6) . ? C5 C6 1.395(8) . ? C6 C7 1.388(8) . ? C8 O4 1.228(6) . ? C8 O3 1.267(6) . ? C8 Cd1 2.744(5) 1_545 ? C9 N1 1.355(6) . ? C9 C10 1.369(7) . ? C10 C11 1.383(7) . ? C11 C12 1.386(7) . ? C12 C13 1.393(7) . ? C12 C14 1.482(6) . ? C13 N1 1.338(6) . ? C14 N2 1.325(6) . ? C14 N3 1.364(6) . ? C15 C16 1.379(6) . ? C15 C20 1.396(7) . ? C15 N2 1.398(6) . ? C16 N3 1.390(6) . ? C16 C17 1.398(7) . ? C17 C18 1.370(8) . ? C18 C19 1.391(8) . ? C19 C20 1.358(8) . ? C21 N3 1.467(6) . ? C21 C22 1.512(6) . ? C22 C22 1.517(9) 2_768 ? N2 Cd1 2.349(4) 2_667 ? O3 Cd1 2.329(4) 1_545 ? O3 Cd1 2.586(4) 2_757 ? O4 Cd1 2.486(4) 1_545 ? 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 O3 120.27(13) . 1_565 ? O1 Cd1 N1 136.38(13) . . ? O3 Cd1 N1 91.71(13) 1_565 . ? O1 Cd1 N2 110.20(13) . 2_667 ? O3 Cd1 N2 102.90(13) 1_565 2_667 ? N1 Cd1 N2 87.85(13) . 2_667 ? O1 Cd1 O4 80.93(13) . 1_565 ? O3 Cd1 O4 53.91(12) 1_565 1_565 ? N1 Cd1 O4 141.69(12) . 1_565 ? N2 Cd1 O4 84.77(14) 2_667 1_565 ? O1 Cd1 O3 74.55(13) . 2_757 ? O3 Cd1 O3 81.55(12) 1_565 2_757 ? N1 Cd1 O3 82.70(12) . 2_757 ? N2 Cd1 O3 169.70(12) 2_667 2_757 ? O4 Cd1 O3 105.21(12) 1_565 2_757 ? O1 Cd1 C8 101.80(14) . 1_565 ? O3 Cd1 C8 27.39(13) 1_565 1_565 ? N1 Cd1 C8 117.09(14) . 1_565 ? N2 Cd1 C8 92.84(14) 2_667 1_565 ? O4 Cd1 C8 26.58(13) 1_565 1_565 ? O3 Cd1 C8 95.10(12) 2_757 1_565 ? O2 C1 O1 123.0(4) . . ? O2 C1 C2 120.8(4) . . ? O1 C1 C2 116.3(4) . . ? C3 C2 C7 119.1(4) . . ? C3 C2 C1 121.7(4) . . ? C7 C2 C1 119.2(4) . . ? C2 C3 C4 120.9(4) . . ? C5 C4 C3 119.8(4) . . ? C5 C4 C8 119.0(4) . . ? C3 C4 C8 121.1(4) . . ? C4 C5 C6 119.5(5) . . ? C7 C6 C5 119.9(5) . . ? C2 C7 C6 120.5(5) . . ? O4 C8 O3 122.5(4) . . ? O4 C8 C4 118.0(4) . . ? O3 C8 C4 119.5(4) . . ? O4 C8 Cd1 64.9(3) . 1_545 ? O3 C8 Cd1 57.8(2) . 1_545 ? C4 C8 Cd1 173.5(3) . 1_545 ? N1 C9 C10 122.8(5) . . ? C9 C10 C11 118.2(5) . . ? C10 C11 C12 120.2(5) . . ? C11 C12 C13 117.9(4) . . ? C11 C12 C14 118.2(4) . . ? C13 C12 C14 123.9(4) . . ? N1 C13 C12 122.3(4) . . ? N2 C14 N3 112.2(4) . . ? N2 C14 C12 122.6(4) . . ? N3 C14 C12 124.8(4) . . ? C16 C15 C20 120.6(4) . . ? C16 C15 N2 109.3(4) . . ? C20 C15 N2 130.1(4) . . ? C15 C16 N3 106.3(4) . . ? C15 C16 C17 122.5(5) . . ? N3 C16 C17 131.1(5) . . ? C18 C17 C16 115.3(5) . . ? C17 C18 C19 122.7(5) . . ? C20 C19 C18 121.5(5) . . ? C19 C20 C15 117.3(5) . . ? N3 C21 C22 113.1(4) . . ? C21 C22 C22 110.7(5) . 2_768 ? C13 N1 C9 118.5(4) . . ? C13 N1 Cd1 126.6(3) . . ? C9 N1 Cd1 114.8(3) . . ? C14 N2 C15 105.5(4) . . ? C14 N2 Cd1 132.6(3) . 2_667 ? C15 N2 Cd1 120.1(3) . 2_667 ? C14 N3 C16 106.6(4) . . ? C14 N3 C21 129.5(4) . . ? C16 N3 C21 123.9(4) . . ? C1 O1 Cd1 102.8(3) . . ? C8 O3 Cd1 94.8(3) . 1_545 ? C8 O3 Cd1 117.6(3) . 2_757 ? Cd1 O3 Cd1 98.45(12) 1_545 2_757 ? C8 O4 Cd1 88.5(3) . 1_545 ? _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.998 _refine_diff_density_min -0.704 _refine_diff_density_rms 0.128 data_7 _database_code_depnum_ccdc_archive 'CCDC 912028' #TrackingRef 'Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 Cd N3 O4' _chemical_formula_weight 498.78 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3800(14) _cell_length_b 20.837(4) _cell_length_c 11.227(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.346(5) _cell_angle_gamma 90.00 _cell_volume 1922.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.724 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 996 _exptl_absorpt_coefficient_mu 1.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7662 _exptl_absorpt_correction_T_max 0.8080 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12001 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0783 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 29.78 _reflns_number_total 4878 _reflns_number_gt 3018 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0291P)^2^+0.0000P] 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 4878 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0634 _refine_ls_goodness_of_fit_ref 0.872 _refine_ls_restrained_S_all 0.872 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.16955(3) 0.063399(11) 0.124847(18) 0.02997(8) Uani 1 1 d . . . C1 C 0.0727(3) -0.06916(16) 0.1348(3) 0.0299(7) Uani 1 1 d . . . C2 C 0.0303(4) -0.13384(15) 0.1814(3) 0.0295(7) Uani 1 1 d . . . C3 C -0.0576(4) -0.13795(15) 0.2727(3) 0.0348(8) Uani 1 1 d . . . H3 H -0.0903 -0.1005 0.3060 0.042 Uiso 1 1 calc R . . C4 C -0.0976(4) -0.19617(16) 0.3154(3) 0.0359(8) Uani 1 1 d . . . H4 H -0.1612 -0.1977 0.3745 0.043 Uiso 1 1 calc R . . C5 C -0.0448(4) -0.25237(15) 0.2717(2) 0.0300(7) Uani 1 1 d . . . C6 C 0.0465(4) -0.24859(16) 0.1810(3) 0.0397(8) Uani 1 1 d . . . H6 H 0.0855 -0.2859 0.1515 0.048 Uiso 1 1 calc R . . C7 C 0.0799(4) -0.18973(16) 0.1345(3) 0.0369(8) Uani 1 1 d . . . H7 H 0.1362 -0.1879 0.0710 0.044 Uiso 1 1 calc R . . C8 C -0.0891(4) -0.31632(16) 0.3174(3) 0.0342(8) Uani 1 1 d . . . C9 C 0.4013(4) 0.11663(17) -0.0436(3) 0.0398(8) Uani 1 1 d . . . H9 H 0.3939 0.1511 0.0077 0.048 Uiso 1 1 calc R . . C10 C 0.4946(5) 0.12317(18) -0.1304(3) 0.0480(9) Uani 1 1 d . . . H10 H 0.5484 0.1616 -0.1380 0.058 Uiso 1 1 calc R . . C11 C 0.5080(4) 0.07233(17) -0.2065(3) 0.0407(8) Uani 1 1 d . . . H11 H 0.5716 0.0758 -0.2653 0.049 Uiso 1 1 calc R . . C12 C 0.4256(4) 0.01643(15) -0.1937(3) 0.0288(7) Uani 1 1 d . . . C13 C 0.3321(4) 0.01353(15) -0.1038(2) 0.0301(7) Uani 1 1 d . . . H13 H 0.2758 -0.0241 -0.0951 0.036 Uiso 1 1 calc R . . C14 C 0.4406(4) -0.03893(15) -0.2736(2) 0.0294(7) Uani 1 1 d . . . C15 C 0.5425(4) -0.11254(15) -0.3709(2) 0.0315(7) Uani 1 1 d . . . C16 C 0.6401(4) -0.15524(17) -0.4210(3) 0.0405(8) Uani 1 1 d . . . H16 H 0.7528 -0.1545 -0.3971 0.049 Uiso 1 1 calc R . . C17 C 0.5649(5) -0.19836(18) -0.5066(3) 0.0456(9) Uani 1 1 d . . . H17 H 0.6276 -0.2281 -0.5387 0.055 Uiso 1 1 calc R . . C18 C 0.3977(5) -0.19840(18) -0.5459(3) 0.0485(9) Uani 1 1 d . . . H18 H 0.3508 -0.2281 -0.6043 0.058 Uiso 1 1 calc R . . C19 C 0.3000(4) -0.15624(18) -0.5015(3) 0.0458(9) Uani 1 1 d . . . H19 H 0.1878 -0.1561 -0.5290 0.055 Uiso 1 1 calc R . . C20 C 0.3757(4) -0.11325(16) -0.4130(3) 0.0343(7) Uani 1 1 d . . . C21 C 0.1403(4) -0.04653(17) -0.3742(3) 0.0373(8) Uani 1 1 d . . . H21A H 0.1191 -0.0225 -0.3049 0.045 Uiso 1 1 calc R . . H21B H 0.0733 -0.0848 -0.3822 0.045 Uiso 1 1 calc R . . C22 C 0.0913(4) -0.00622(16) -0.4869(3) 0.0350(8) Uani 1 1 d . . . H22A H 0.1211 -0.0282 -0.5556 0.042 Uiso 1 1 calc R . . H22B H 0.1490 0.0344 -0.4762 0.042 Uiso 1 1 calc R . . N1 N 0.3204(3) 0.06260(13) -0.0298(2) 0.0304(5) Uani 1 1 d . . . N2 N 0.5821(3) -0.06548(13) -0.2811(2) 0.0310(6) Uani 1 1 d . . . N3 N 0.3123(3) -0.06566(13) -0.3504(2) 0.0319(6) Uani 1 1 d . . . O1 O 0.0864(3) -0.06437(11) 0.02726(18) 0.0423(5) Uani 1 1 d . . . O2 O 0.0915(3) -0.02418(11) 0.2098(2) 0.0428(6) Uani 1 1 d . . . O3 O -0.0258(3) -0.36542(11) 0.2818(2) 0.0470(6) Uani 1 1 d . . . O4 O -0.1906(3) -0.31885(11) 0.38423(19) 0.0443(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 Cd1 0.03419(13) 0.02025(11) 0.03882(12) -0.00088(11) 0.01536(9) 0.00038(13) C1 0.0231(15) 0.0229(17) 0.0432(17) 0.0046(15) 0.0056(13) 0.0027(15) C2 0.0286(18) 0.0243(18) 0.0346(16) 0.0015(13) 0.0039(14) -0.0035(14) C3 0.041(2) 0.0197(17) 0.0469(18) -0.0025(14) 0.0155(16) -0.0015(15) C4 0.041(2) 0.0298(19) 0.0408(16) -0.0011(14) 0.0177(15) -0.0091(17) C5 0.0332(18) 0.0207(17) 0.0358(15) 0.0018(13) 0.0060(14) -0.0078(15) C6 0.049(2) 0.0232(19) 0.0520(19) -0.0065(15) 0.0216(17) -0.0042(17) C7 0.048(2) 0.0296(19) 0.0368(16) 0.0020(14) 0.0164(15) -0.0040(17) C8 0.039(2) 0.0252(19) 0.0383(17) 0.0038(14) 0.0072(15) -0.0090(16) C9 0.040(2) 0.0297(19) 0.054(2) -0.0084(16) 0.0196(16) -0.0047(17) C10 0.047(2) 0.036(2) 0.068(2) -0.0069(18) 0.0304(19) -0.0077(18) C11 0.0385(19) 0.040(2) 0.0493(18) -0.0004(16) 0.0231(15) 0.0018(17) C12 0.0253(17) 0.0273(18) 0.0343(16) 0.0027(13) 0.0071(14) 0.0059(15) C13 0.0290(17) 0.0252(17) 0.0356(17) 0.0017(13) 0.0054(14) 0.0033(15) C14 0.0279(17) 0.0319(17) 0.0296(15) 0.0029(13) 0.0084(14) 0.0057(15) C15 0.0310(18) 0.0297(18) 0.0350(16) 0.0002(14) 0.0094(14) 0.0057(15) C16 0.034(2) 0.041(2) 0.0475(18) -0.0052(16) 0.0112(16) 0.0050(17) C17 0.052(2) 0.038(2) 0.0505(19) -0.0100(16) 0.0201(18) 0.0093(19) C18 0.056(3) 0.044(2) 0.0463(19) -0.0172(17) 0.0102(18) -0.004(2) C19 0.034(2) 0.054(2) 0.0470(19) -0.0061(18) 0.0003(16) 0.0025(19) C20 0.0352(19) 0.0344(19) 0.0344(16) -0.0003(14) 0.0093(14) 0.0063(16) C21 0.0276(19) 0.045(2) 0.0402(17) 0.0003(15) 0.0073(15) 0.0085(15) C22 0.0294(18) 0.038(2) 0.0385(17) 0.0019(14) 0.0095(15) 0.0069(16) N1 0.0298(14) 0.0260(14) 0.0375(12) -0.0029(12) 0.0118(10) 0.0058(14) N2 0.0256(13) 0.0332(15) 0.0349(12) -0.0021(12) 0.0074(10) 0.0067(14) N3 0.0270(14) 0.0349(15) 0.0344(12) -0.0009(13) 0.0070(11) 0.0098(14) O1 0.0468(14) 0.0358(13) 0.0464(12) 0.0132(11) 0.0141(10) -0.0018(13) O2 0.0522(16) 0.0240(14) 0.0533(13) 0.0021(11) 0.0131(12) -0.0073(12) O3 0.0583(17) 0.0218(13) 0.0678(15) 0.0038(11) 0.0288(13) -0.0003(12) O4 0.0534(16) 0.0322(14) 0.0531(13) 0.0052(11) 0.0245(12) -0.0086(12) _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 O2 2.217(2) . ? Cd1 O3 2.290(2) 2 ? Cd1 N1 2.340(2) . ? Cd1 N2 2.444(2) 3_655 ? Cd1 O4 2.463(2) 2 ? Cd1 O1 2.465(2) 3 ? Cd1 C8 2.707(3) 2 ? C1 O1 1.239(3) . ? C1 O2 1.249(4) . ? C1 C2 1.513(4) . ? C2 C7 1.376(4) . ? C2 C3 1.378(4) . ? C3 C4 1.370(4) . ? C3 H3 0.9300 . ? C4 C5 1.376(4) . ? C4 H4 0.9300 . ? C5 C6 1.391(4) . ? C5 C8 1.500(4) . ? C6 C7 1.383(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O4 1.241(4) . ? C8 O3 1.253(4) . ? C8 Cd1 2.707(3) 2_545 ? C9 N1 1.339(4) . ? C9 C10 1.372(4) . ? C9 H9 0.9300 . ? C10 C11 1.379(5) . ? C10 H10 0.9300 . ? C11 C12 1.375(5) . ? C11 H11 0.9300 . ? C12 C13 1.396(4) . ? C12 C14 1.482(4) . ? C13 N1 1.333(4) . ? C13 H13 0.9300 . ? C14 N2 1.326(4) . ? C14 N3 1.358(4) . ? C15 C20 1.385(4) . ? C15 N2 1.399(4) . ? C15 C16 1.399(4) . ? C16 C17 1.374(5) . ? C16 H16 0.9300 . ? C17 C18 1.384(5) . ? C17 H17 0.9300 . ? C18 C19 1.361(5) . ? C18 H18 0.9300 . ? C19 C20 1.394(5) . ? C19 H19 0.9300 . ? C20 N3 1.381(4) . ? C21 N3 1.468(4) . ? C21 C22 1.508(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C22 1.522(6) 3_554 ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? N2 Cd1 2.444(2) 3_655 ? O1 Cd1 2.465(2) 3 ? O3 Cd1 2.290(2) 2_545 ? O4 Cd1 2.463(2) 2_545 ? 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 O2 Cd1 O3 96.31(9) . 2 ? O2 Cd1 N1 124.17(9) . . ? O3 Cd1 N1 138.90(9) 2 . ? O2 Cd1 N2 89.28(9) . 3_655 ? O3 Cd1 N2 96.35(9) 2 3_655 ? N1 Cd1 N2 91.41(8) . 3_655 ? O2 Cd1 O4 150.15(8) . 2 ? O3 Cd1 O4 54.71(8) 2 2 ? N1 Cd1 O4 85.58(8) . 2 ? N2 Cd1 O4 87.38(9) 3_655 2 ? O2 Cd1 O1 90.84(8) . 3 ? O3 Cd1 O1 81.22(8) 2 3 ? N1 Cd1 O1 90.53(8) . 3 ? N2 Cd1 O1 177.56(8) 3_655 3 ? O4 Cd1 O1 91.30(8) 2 3 ? O2 Cd1 C8 123.40(10) . 2 ? O3 Cd1 C8 27.46(9) 2 2 ? N1 Cd1 C8 112.38(10) . 2 ? N2 Cd1 C8 91.64(9) 3_655 2 ? O4 Cd1 C8 27.26(9) 2 2 ? O1 Cd1 C8 86.26(9) 3 2 ? O1 C1 O2 125.0(3) . . ? O1 C1 C2 118.8(3) . . ? O2 C1 C2 116.2(3) . . ? C7 C2 C3 118.6(3) . . ? C7 C2 C1 120.8(3) . . ? C3 C2 C1 120.6(3) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 118.3(3) . . ? C4 C5 C8 121.0(3) . . ? C6 C5 C8 120.6(3) . . ? C7 C6 C5 120.5(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C2 C7 C6 120.5(3) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? O4 C8 O3 122.8(3) . . ? O4 C8 C5 119.3(3) . . ? O3 C8 C5 117.9(3) . . ? O4 C8 Cd1 65.37(17) . 2_545 ? O3 C8 Cd1 57.42(17) . 2_545 ? C5 C8 Cd1 173.8(2) . 2_545 ? N1 C9 C10 122.6(3) . . ? N1 C9 H9 118.7 . . ? C10 C9 H9 118.7 . . ? C9 C10 C11 119.4(3) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 118.9(3) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C13 118.4(3) . . ? C11 C12 C14 119.5(3) . . ? C13 C12 C14 122.0(3) . . ? N1 C13 C12 122.5(3) . . ? N1 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? N2 C14 N3 113.2(3) . . ? N2 C14 C12 123.1(3) . . ? N3 C14 C12 123.6(3) . . ? C20 C15 N2 109.5(3) . . ? C20 C15 C16 119.1(3) . . ? N2 C15 C16 131.4(3) . . ? C17 C16 C15 118.2(3) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C16 C17 C18 121.3(3) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C19 C18 C17 121.8(3) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C20 117.0(3) . . ? C18 C19 H19 121.5 . . ? C20 C19 H19 121.5 . . ? N3 C20 C15 106.4(3) . . ? N3 C20 C19 131.1(3) . . ? C15 C20 C19 122.5(3) . . ? N3 C21 C22 113.6(2) . . ? N3 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? N3 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C22 110.8(3) . 3_554 ? C21 C22 H22A 109.5 . . ? C22 C22 H22A 109.5 3_554 . ? C21 C22 H22B 109.5 . . ? C22 C22 H22B 109.5 3_554 . ? H22A C22 H22B 108.1 . . ? C13 N1 C9 118.2(3) . . ? C13 N1 Cd1 125.8(2) . . ? C9 N1 Cd1 116.1(2) . . ? C14 N2 C15 104.5(2) . . ? C14 N2 Cd1 126.37(19) . 3_655 ? C15 N2 Cd1 125.26(19) . 3_655 ? C14 N3 C20 106.4(2) . . ? C14 N3 C21 129.0(3) . . ? C20 N3 C21 124.4(3) . . ? C1 O1 Cd1 116.19(19) . 3 ? C1 O2 Cd1 109.63(19) . . ? C8 O3 Cd1 95.12(19) . 2_545 ? C8 O4 Cd1 87.4(2) . 2_545 ? 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 O1 C1 C2 C7 31.1(4) . . . . ? O2 C1 C2 C7 -148.9(3) . . . . ? O1 C1 C2 C3 -149.6(3) . . . . ? O2 C1 C2 C3 30.5(4) . . . . ? C7 C2 C3 C4 -1.0(5) . . . . ? C1 C2 C3 C4 179.6(3) . . . . ? C2 C3 C4 C5 2.9(5) . . . . ? C3 C4 C5 C6 -1.6(5) . . . . ? C3 C4 C5 C8 -179.6(3) . . . . ? C4 C5 C6 C7 -1.4(5) . . . . ? C8 C5 C6 C7 176.5(3) . . . . ? C3 C2 C7 C6 -2.1(5) . . . . ? C1 C2 C7 C6 177.3(3) . . . . ? C5 C6 C7 C2 3.3(5) . . . . ? C4 C5 C8 O4 8.8(5) . . . . ? C6 C5 C8 O4 -169.1(3) . . . . ? C4 C5 C8 O3 -173.9(3) . . . . ? C6 C5 C8 O3 8.2(4) . . . . ? C4 C5 C8 Cd1 146(2) . . . 2_545 ? C6 C5 C8 Cd1 -32(2) . . . 2_545 ? N1 C9 C10 C11 -0.6(5) . . . . ? C9 C10 C11 C12 0.6(5) . . . . ? C10 C11 C12 C13 -0.2(5) . . . . ? C10 C11 C12 C14 -179.2(3) . . . . ? C11 C12 C13 N1 -0.3(4) . . . . ? C14 C12 C13 N1 178.6(3) . . . . ? C11 C12 C14 N2 57.2(4) . . . . ? C13 C12 C14 N2 -121.8(3) . . . . ? C11 C12 C14 N3 -119.7(3) . . . . ? C13 C12 C14 N3 61.3(4) . . . . ? C20 C15 C16 C17 -2.9(5) . . . . ? N2 C15 C16 C17 177.7(3) . . . . ? C15 C16 C17 C18 2.3(5) . . . . ? C16 C17 C18 C19 -0.4(6) . . . . ? C17 C18 C19 C20 -0.8(5) . . . . ? N2 C15 C20 N3 1.1(3) . . . . ? C16 C15 C20 N3 -178.5(3) . . . . ? N2 C15 C20 C19 -178.7(3) . . . . ? C16 C15 C20 C19 1.8(5) . . . . ? C18 C19 C20 N3 -179.6(3) . . . . ? C18 C19 C20 C15 0.1(5) . . . . ? N3 C21 C22 C22 174.3(3) . . . 3_554 ? C12 C13 N1 C9 0.3(4) . . . . ? C12 C13 N1 Cd1 -179.5(2) . . . . ? C10 C9 N1 C13 0.1(5) . . . . ? C10 C9 N1 Cd1 -180.0(3) . . . . ? O2 Cd1 N1 C13 20.8(3) . . . . ? O3 Cd1 N1 C13 -147.8(2) 2 . . . ? N2 Cd1 N1 C13 110.9(2) 3_655 . . . ? O4 Cd1 N1 C13 -161.8(2) 2 . . . ? O1 Cd1 N1 C13 -70.6(2) 3 . . . ? C8 Cd1 N1 C13 -156.7(2) 2 . . . ? O2 Cd1 N1 C9 -159.1(2) . . . . ? O3 Cd1 N1 C9 32.3(3) 2 . . . ? N2 Cd1 N1 C9 -69.0(2) 3_655 . . . ? O4 Cd1 N1 C9 18.3(2) 2 . . . ? O1 Cd1 N1 C9 109.5(2) 3 . . . ? C8 Cd1 N1 C9 23.4(2) 2 . . . ? N3 C14 N2 C15 0.8(3) . . . . ? C12 C14 N2 C15 -176.3(3) . . . . ? N3 C14 N2 Cd1 -157.74(19) . . . 3_655 ? C12 C14 N2 Cd1 25.1(4) . . . 3_655 ? C20 C15 N2 C14 -1.1(3) . . . . ? C16 C15 N2 C14 178.3(3) . . . . ? C20 C15 N2 Cd1 157.7(2) . . . 3_655 ? C16 C15 N2 Cd1 -22.8(5) . . . 3_655 ? N2 C14 N3 C20 -0.2(3) . . . . ? C12 C14 N3 C20 177.0(3) . . . . ? N2 C14 N3 C21 -175.3(3) . . . . ? C12 C14 N3 C21 1.9(5) . . . . ? C15 C20 N3 C14 -0.5(3) . . . . ? C19 C20 N3 C14 179.2(3) . . . . ? C15 C20 N3 C21 174.9(3) . . . . ? C19 C20 N3 C21 -5.4(5) . . . . ? C22 C21 N3 C14 98.4(3) . . . . ? C22 C21 N3 C20 -75.9(4) . . . . ? O2 C1 O1 Cd1 -104.6(3) . . . 3 ? C2 C1 O1 Cd1 75.5(3) . . . 3 ? O1 C1 O2 Cd1 -4.0(4) . . . . ? C2 C1 O2 Cd1 176.0(2) . . . . ? O3 Cd1 O2 C1 143.2(2) 2 . . . ? N1 Cd1 O2 C1 -29.3(2) . . . . ? N2 Cd1 O2 C1 -120.5(2) 3_655 . . . ? O4 Cd1 O2 C1 156.03(19) 2 . . . ? O1 Cd1 O2 C1 61.9(2) 3 . . . ? C8 Cd1 O2 C1 148.0(2) 2 . . . ? O4 C8 O3 Cd1 1.9(3) . . . 2_545 ? C5 C8 O3 Cd1 -175.3(2) . . . 2_545 ? O3 C8 O4 Cd1 -1.7(3) . . . 2_545 ? C5 C8 O4 Cd1 175.4(3) . . . 2_545 ? _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 29.78 _diffrn_measured_fraction_theta_full 0.887 _refine_diff_density_max 0.815 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.087 data_8 _database_code_depnum_ccdc_archive 'CCDC 912029' #TrackingRef 'Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H30 Cd2 N6 O10' _chemical_formula_weight 1039.55 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 _symmetry_space_group_name_Hall '-C 2yc' 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 10.393(2) _cell_length_b 23.046(6) _cell_length_c 28.526(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.381(4) _cell_angle_gamma 90.00 _cell_volume 6802(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.015 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2072 _exptl_absorpt_coefficient_mu 0.667 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8672 _exptl_absorpt_correction_T_max 0.9124 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21402 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.1117 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.35 _reflns_number_total 6116 _reflns_number_gt 2560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 distances of C5...C9 and C5'...C9 were restrained to 1.50+-0.01 \%A. The distance of O3'...O4' was restrained to 2.00+-0.01 \%A. For C5 atom, the anisotropic displacement ellipsoid was rather elongated which led us to use the simu restraint. ; _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^)+(0.0850P)^2^+0.0000P] 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 6116 _refine_ls_number_parameters 322 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1699 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.1906 _refine_ls_wR_factor_gt 0.1722 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 Cd1 Cd 0.52161(5) 0.20250(4) 0.022231(17) 0.1123(4) Uani 1 1 d . . . C1 C 0.7086(8) 0.2162(5) 0.0938(3) 0.087(3) Uani 1 1 d . B . C2 C 0.8174(7) 0.2305(4) 0.1311(2) 0.104(3) Uani 1 1 d . . . C3 C 0.8046(8) 0.2201(5) 0.1774(3) 0.141(5) Uani 1 1 d . B . H3 H 0.7358 0.1975 0.1853 0.169 Uiso 1 1 calc R A 1 C7 C 0.9302(7) 0.2553(5) 0.1199(2) 0.117(4) Uani 1 1 d . B . C8 C 0.9562(9) 0.2720(7) 0.0686(4) 0.111(4) Uani 1 1 d . . . C10 C 0.4467(7) 0.0679(6) 0.0480(3) 0.107(3) Uani 1 1 d . . . C11 C 0.5486(8) 0.0561(6) 0.0839(3) 0.109(3) Uani 1 1 d . B . H11 H 0.6068 0.0852 0.0938 0.131 Uiso 1 1 calc R . . C12 C 0.5602(9) 0.0054(7) 0.1028(4) 0.128(4) Uani 1 1 d . . . H12 H 0.6237 -0.0007 0.1275 0.153 Uiso 1 1 calc R B . C13 C 0.4801(9) -0.0408(6) 0.0872(4) 0.133(4) Uani 1 1 d . B . H13 H 0.4927 -0.0774 0.1004 0.160 Uiso 1 1 calc R . . C14 C 0.3756(8) -0.0308(7) 0.0497(4) 0.127(4) Uani 1 1 d . . . H14 H 0.3193 -0.0601 0.0385 0.152 Uiso 1 1 calc R B . C15 C 0.3669(8) 0.0248(6) 0.0322(3) 0.096(3) Uani 1 1 d . B . C16 C 0.3086(7) 0.1010(6) -0.0074(3) 0.102(4) Uani 1 1 d . . . C17 C 0.2375(8) 0.1432(6) -0.0404(3) 0.108(4) Uani 1 1 d . B . C18 C 0.2304(7) 0.1324(5) -0.0884(3) 0.120(4) Uani 1 1 d . . . H18 H 0.2657 0.0990 -0.1002 0.143 Uiso 1 1 calc R B . C19 C 0.1684(9) 0.1734(6) -0.1181(3) 0.123(4) Uani 1 1 d . B . H19 H 0.1649 0.1688 -0.1506 0.148 Uiso 1 1 calc R . . C20 C 0.1121(8) 0.2208(6) -0.0992(3) 0.116(4) Uani 1 1 d . . . H20 H 0.0701 0.2479 -0.1193 0.139 Uiso 1 1 calc R B . C21 C 0.1771(8) 0.1902(6) -0.0235(3) 0.096(3) Uani 1 1 d . . . H21 H 0.1786 0.1951 0.0089 0.116 Uiso 1 1 calc R B . C22 C 0.1660(6) 0.0113(4) -0.0237(3) 0.105(3) Uani 1 1 d . . . H22A H 0.1918 -0.0287 -0.0274 0.126 Uiso 1 1 calc R B . H22B H 0.1349 0.0265 -0.0544 0.126 Uiso 1 1 calc R . . C23 C 0.0585(6) 0.0152(4) 0.0105(3) 0.101(3) Uani 1 1 d . . . H23A H 0.0882 -0.0024 0.0404 0.121 Uiso 1 1 calc R . . H23B H 0.0382 0.0556 0.0161 0.121 Uiso 1 1 calc R . . N1 N 0.4117(5) 0.1169(4) 0.0234(2) 0.111(3) Uani 1 1 d . B . N2 N 0.2796(6) 0.0469(5) -0.0025(2) 0.106(3) Uani 1 1 d . B . N3 N 0.1160(5) 0.2293(3) -0.0518(2) 0.094(2) Uani 1 1 d . . . C9 C 1.1301(13) 0.2446(11) 0.2354(5) 0.144(9) Uani 0.50 1 d PD . . O5 O 1.2465(10) 0.2376(7) 0.2251(3) 0.141(6) Uani 0.50 1 d P B . O1 O 0.7056(8) 0.2375(7) 0.0556(3) 0.163(6) Uani 0.822(13) 1 d P B 1 O2 O 0.6176(10) 0.1889(8) 0.1036(3) 0.137(5) Uani 0.822(13) 1 d P B 1 C4 C 0.8915(10) 0.2422(10) 0.2135(3) 0.145(8) Uani 0.822(13) 1 d P . 1 C5 C 1.0120(12) 0.2589(12) 0.2011(4) 0.199(13) Uani 0.822(13) 1 d PD B 1 C6 C 1.0172(13) 0.2733(12) 0.1546(5) 0.182(10) Uani 0.822(13) 1 d P B 1 H6 H 1.0848 0.2968 0.1468 0.218 Uiso 0.822(13) 1 calc PR B 1 O3 O 0.9040(10) 0.3155(6) 0.0527(3) 0.163(5) Uani 0.822(13) 1 d P . 1 O1' O 0.742(2) 0.1835(13) 0.0567(10) 0.059(9) Uiso 0.178(13) 1 d P B 2 O2' O 0.621(6) 0.2276(18) 0.1014(15) 0.084(14) Uiso 0.178(13) 1 d P B 2 C4' C 0.917(3) 0.1956(16) 0.2086(12) 0.033(9) Uiso 0.178(13) 1 d P B 2 C5' C 1.022(4) 0.222(2) 0.2012(19) 0.061(16) Uiso 0.178(13) 1 d PD B 2 C6' C 1.054(4) 0.2534(17) 0.1546(14) 0.022(9) Uiso 0.178(13) 1 d P B 2 H6' H 1.1346 0.2681 0.1488 0.027 Uiso 0.178(13) 1 calc PR B 2 O3' O 1.001(3) 0.3200(9) 0.0619(10) 0.077(11) Uiso 0.178(13) 1 d PD . 2 O4 O 1.0462(18) 0.2497(8) 0.0506(6) 0.133(5) Uiso 0.50 1 d P . . O4' O 0.9767(19) 0.2363(8) 0.0453(7) 0.141(7) Uiso 0.50 1 d PD . . O1W O 0.6309(11) 0.3340(14) 0.0157(6) 0.292(16) Uani 0.50 1 d P . . 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 0.0624(4) 0.2339(9) 0.0379(3) 0.0139(4) -0.0087(2) -0.0405(4) C1 0.072(5) 0.151(10) 0.038(4) -0.001(5) -0.006(3) -0.004(7) C2 0.064(4) 0.210(11) 0.037(4) 0.015(5) -0.007(3) -0.042(5) C3 0.077(5) 0.295(15) 0.047(5) 0.029(6) -0.009(4) -0.047(6) C7 0.087(5) 0.236(11) 0.024(4) -0.007(5) -0.009(3) -0.075(6) C8 0.058(6) 0.152(12) 0.116(9) 0.003(9) -0.036(6) -0.030(6) C10 0.068(5) 0.193(11) 0.057(5) 0.028(6) -0.003(4) -0.047(6) C11 0.078(5) 0.170(12) 0.078(6) 0.010(6) 0.003(4) -0.039(6) C12 0.077(6) 0.190(14) 0.115(8) 0.025(9) -0.003(5) -0.030(8) C13 0.080(6) 0.217(14) 0.106(7) 0.064(8) 0.023(6) 0.008(7) C14 0.069(5) 0.215(14) 0.099(7) -0.005(8) 0.026(5) -0.033(7) C15 0.070(5) 0.156(11) 0.065(5) 0.021(6) 0.018(4) -0.028(6) C16 0.057(5) 0.196(12) 0.055(5) 0.015(6) 0.014(4) -0.044(6) C17 0.054(4) 0.224(12) 0.044(5) 0.036(6) -0.004(4) -0.038(6) C18 0.077(5) 0.229(12) 0.051(5) -0.003(6) -0.002(4) -0.021(6) C19 0.082(6) 0.246(14) 0.042(5) 0.005(7) 0.000(4) -0.001(7) C20 0.063(5) 0.233(14) 0.050(5) 0.022(6) 0.001(4) -0.040(6) C21 0.056(4) 0.187(11) 0.045(4) 0.015(6) 0.000(4) -0.049(5) C22 0.062(4) 0.172(9) 0.081(5) 0.001(6) 0.004(4) -0.039(5) C23 0.056(4) 0.167(9) 0.080(5) 0.007(5) 0.013(4) -0.034(4) N1 0.058(4) 0.227(10) 0.050(4) -0.014(5) 0.007(3) -0.040(5) N2 0.046(3) 0.212(10) 0.061(4) 0.004(5) 0.004(3) -0.037(5) N3 0.064(3) 0.172(8) 0.044(3) 0.016(4) -0.006(3) -0.026(4) C9 0.062(10) 0.33(3) 0.037(8) -0.007(13) 0.007(7) -0.041(13) O5 0.073(7) 0.308(19) 0.039(5) -0.019(8) -0.009(5) -0.014(8) O1 0.098(6) 0.321(19) 0.064(5) 0.058(7) -0.031(4) -0.078(8) O2 0.082(5) 0.252(17) 0.071(5) 0.028(7) -0.018(4) -0.077(8) C4 0.074(7) 0.33(3) 0.031(5) 0.018(9) -0.009(5) -0.044(11) C5 0.094(9) 0.47(4) 0.025(5) 0.013(13) -0.013(5) -0.118(16) C6 0.062(8) 0.42(3) 0.058(7) -0.001(13) -0.003(7) -0.064(13) O3 0.086(7) 0.320(16) 0.087(6) 0.023(7) 0.025(5) 0.021(7) O1W 0.065(7) 0.69(5) 0.124(13) -0.19(2) 0.007(8) 0.003(15) _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 2.207(7) . ? Cd1 N1 2.283(9) . ? Cd1 N3 2.335(7) 7 ? Cd1 O3 2.377(8) 7_655 ? Cd1 O4' 2.388(18) 7_655 ? Cd1 O4 2.399(16) 7_655 ? Cd1 O1' 2.45(3) . ? Cd1 O3' 2.45(3) 7_655 ? Cd1 O2 2.460(7) . ? Cd1 O2' 2.46(4) . ? Cd1 C8 2.687(11) 7_655 ? Cd1 C1 2.702(7) . ? C1 O2' 0.99(5) . ? C1 O2 1.190(11) . ? C1 O1 1.192(10) . ? C1 O1' 1.37(3) . ? C1 C2 1.514(9) . ? C2 C3 1.362(10) . ? C2 C7 1.369(10) . ? C3 C4 1.399(13) . ? C3 C4' 1.51(3) . ? C7 C6 1.344(15) . ? C7 C6' 1.55(4) . ? C7 C8 1.561(13) . ? C8 O4' 1.091(17) . ? C8 O3 1.207(14) . ? C8 O4 1.22(2) . ? C8 O3' 1.22(2) . ? C8 Cd1 2.687(11) 7_655 ? C10 C15 1.345(12) . ? C10 N1 1.360(12) . ? C10 C11 1.430(12) . ? C11 C12 1.287(13) . ? C12 C13 1.397(15) . ? C13 C14 1.469(13) . ? C14 C15 1.373(14) . ? C15 N2 1.376(11) . ? C16 N2 1.294(12) . ? C16 N1 1.369(9) . ? C16 C17 1.500(13) . ? C17 C21 1.361(13) . ? C17 C18 1.388(12) . ? C18 C19 1.386(13) . ? C19 C20 1.374(14) . ? C20 N3 1.363(10) . ? C21 N3 1.331(11) . ? C22 N2 1.516(10) . ? C22 C23 1.553(10) . ? C23 C23 1.480(13) 5 ? N3 Cd1 2.335(7) 7 ? C9 O5 1.282(17) . ? C9 C4 1.497(17) 2_755 ? C9 C5' 1.509(10) . ? C9 C5 1.532(9) . ? C4 C5 1.388(16) . ? C4 C9 1.497(17) 2_755 ? C5 C6 1.372(19) . ? O3 Cd1 2.377(8) 7_655 ? C4' C5' 1.29(6) . ? C5' C6' 1.57(8) . ? O3' O4 1.72(3) . ? O3' Cd1 2.45(3) 7_655 ? O4 O4' 0.79(2) . ? O4 Cd1 2.399(16) 7_655 ? O4' Cd1 2.388(18) 7_655 ? 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 N1 136.4(4) . . ? O1 Cd1 N3 97.7(4) . 7 ? N1 Cd1 N3 104.6(2) . 7 ? O1 Cd1 O3 96.3(4) . 7_655 ? N1 Cd1 O3 93.9(3) . 7_655 ? N3 Cd1 O3 134.8(4) 7 7_655 ? O1 Cd1 O4' 93.5(6) . 7_655 ? N1 Cd1 O4' 124.3(5) . 7_655 ? N3 Cd1 O4' 86.8(5) 7 7_655 ? O3 Cd1 O4' 49.5(6) 7_655 7_655 ? O1 Cd1 O4 112.3(5) . 7_655 ? N1 Cd1 O4 107.6(5) . 7_655 ? N3 Cd1 O4 82.2(5) 7 7_655 ? O3 Cd1 O4 52.7(5) 7_655 7_655 ? O4' Cd1 O4 18.9(5) 7_655 7_655 ? O1 Cd1 O1' 31.9(6) . . ? N1 Cd1 O1' 106.9(7) . . ? N3 Cd1 O1' 123.9(7) 7 . ? O3 Cd1 O1' 87.7(7) 7_655 . ? O4' Cd1 O1' 110.7(9) 7_655 . ? O4 Cd1 O1' 128.2(8) 7_655 . ? O1 Cd1 O3' 120.1(8) . 7_655 ? N1 Cd1 O3' 80.1(7) . 7_655 ? N3 Cd1 O3' 119.4(7) 7 7_655 ? O3 Cd1 O3' 24.5(7) 7_655 7_655 ? O4' Cd1 O3' 48.8(4) 7_655 7_655 ? O4 Cd1 O3' 41.7(8) 7_655 7_655 ? O1' Cd1 O3' 111.0(10) . 7_655 ? O1 Cd1 O2 51.7(3) . . ? N1 Cd1 O2 92.1(4) . . ? N3 Cd1 O2 87.3(4) 7 . ? O3 Cd1 O2 133.6(5) 7_655 . ? O4' Cd1 O2 143.4(6) 7_655 . ? O4 Cd1 O2 159.5(6) 7_655 . ? O1' Cd1 O2 46.8(7) . . ? O3' Cd1 O2 153.3(8) 7_655 . ? O1 Cd1 O2' 41.1(15) . . ? N1 Cd1 O2' 110.9(13) . . ? N3 Cd1 O2' 74.3(11) 7 . ? O3 Cd1 O2' 136.2(14) 7_655 . ? O4' Cd1 O2' 124.5(13) 7_655 . ? O4 Cd1 O2' 138.7(11) 7_655 . ? O1' Cd1 O2' 51.4(14) . . ? O3' Cd1 O2' 160.7(17) 7_655 . ? O2 Cd1 O2' 20.9(9) . . ? O1 Cd1 C8 100.8(3) . 7_655 ? N1 Cd1 C8 106.9(3) . 7_655 ? N3 Cd1 C8 108.2(4) 7 7_655 ? O3 Cd1 C8 26.7(4) 7_655 7_655 ? O4' Cd1 C8 23.9(4) 7_655 7_655 ? O4 Cd1 C8 27.0(5) 7_655 7_655 ? O1' Cd1 C8 105.4(7) . 7_655 ? O3' Cd1 C8 27.1(5) 7_655 7_655 ? O2 Cd1 C8 150.9(3) . 7_655 ? O2' Cd1 C8 140.0(14) . 7_655 ? O1 Cd1 C1 25.7(3) . . ? N1 Cd1 C1 114.6(3) . . ? N3 Cd1 C1 94.0(3) 7 . ? O3 Cd1 C1 115.4(3) 7_655 . ? O4' Cd1 C1 118.8(5) 7_655 . ? O4 Cd1 C1 137.2(5) 7_655 . ? O1' Cd1 C1 30.3(7) . . ? O3' Cd1 C1 139.8(9) 7_655 . ? O2 Cd1 C1 26.1(3) . . ? O2' Cd1 C1 21.5(12) . . ? C8 Cd1 C1 125.6(3) 7_655 . ? O2' C1 O2 47(2) . . ? O2' C1 O1 98(3) . . ? O2 C1 O1 118.6(8) . . ? O2' C1 O1' 128(3) . . ? O2 C1 O1' 98.9(16) . . ? O1 C1 O1' 60.5(12) . . ? O2' C1 C2 116(3) . . ? O2 C1 C2 120.5(7) . . ? O1 C1 C2 120.3(9) . . ? O1' C1 C2 115.9(12) . . ? O2' C1 Cd1 65(2) . . ? O2 C1 Cd1 65.5(5) . . ? O1 C1 Cd1 53.3(4) . . ? O1' C1 Cd1 64.4(11) . . ? C2 C1 Cd1 173.1(7) . . ? C3 C2 C7 117.7(6) . . ? C3 C2 C1 120.5(7) . . ? C7 C2 C1 121.8(6) . . ? C2 C3 C4 122.3(9) . . ? C2 C3 C4' 120.0(15) . . ? C4 C3 C4' 45.0(13) . . ? C6 C7 C2 119.2(9) . . ? C6 C7 C6' 22.5(19) . . ? C2 C7 C6' 121.2(17) . . ? C6 C7 C8 116.9(9) . . ? C2 C7 C8 123.3(5) . . ? C6' C7 C8 113.5(17) . . ? O4' C8 O3 120.3(15) . . ? O4' C8 O4 39.3(13) . . ? O3 C8 O4 121.9(13) . . ? O4' C8 O3' 119.2(19) . . ? O3 C8 O3' 50.0(16) . . ? O4 C8 O3' 89.8(18) . . ? O4' C8 C7 116.5(16) . . ? O3 C8 C7 116.4(13) . . ? O4 C8 C7 119.7(12) . . ? O3' C8 C7 118.0(16) . . ? O4' C8 Cd1 62.5(12) . 7_655 ? O3 C8 Cd1 62.2(7) . 7_655 ? O4 C8 Cd1 63.2(9) . 7_655 ? O3' C8 Cd1 65.4(14) . 7_655 ? C7 C8 Cd1 174.7(5) . 7_655 ? C15 C10 N1 108.3(8) . . ? C15 C10 C11 119.4(11) . . ? N1 C10 C11 132.3(10) . . ? C12 C11 C10 120.4(10) . . ? C11 C12 C13 121.9(11) . . ? C12 C13 C14 119.4(11) . . ? C15 C14 C13 115.4(10) . . ? C10 C15 C14 123.4(9) . . ? C10 C15 N2 108.1(10) . . ? C14 C15 N2 128.5(10) . . ? N2 C16 N1 111.3(9) . . ? N2 C16 C17 126.0(8) . . ? N1 C16 C17 122.7(11) . . ? C21 C17 C18 120.6(9) . . ? C21 C17 C16 120.6(8) . . ? C18 C17 C16 118.8(12) . . ? C19 C18 C17 117.3(11) . . ? C20 C19 C18 119.5(9) . . ? N3 C20 C19 122.1(9) . . ? N3 C21 C17 122.2(8) . . ? N2 C22 C23 107.3(6) . . ? C23 C23 C22 109.4(8) 5 . ? C10 N1 C16 105.4(9) . . ? C10 N1 Cd1 127.9(5) . . ? C16 N1 Cd1 125.8(8) . . ? C16 N2 C15 106.9(8) . . ? C16 N2 C22 131.2(8) . . ? C15 N2 C22 121.5(9) . . ? C21 N3 C20 118.1(9) . . ? C21 N3 Cd1 120.7(6) . 7 ? C20 N3 Cd1 119.6(6) . 7 ? O5 C9 C4 116.7(10) . 2_755 ? O5 C9 C5' 118(3) . . ? C4 C9 C5' 117(3) 2_755 . ? O5 C9 C5 126.6(13) . . ? C4 C9 C5 116.5(11) 2_755 . ? C5' C9 C5 32(2) . . ? C1 O1 Cd1 101.0(6) . . ? C1 O2 Cd1 88.4(6) . . ? C5 C4 C3 116.7(10) . . ? C5 C4 C9 117.3(10) . 2_755 ? C3 C4 C9 125.8(10) . 2_755 ? C6 C5 C4 115.6(9) . . ? C6 C5 C9 124.5(13) . . ? C4 C5 C9 117.7(13) . . ? C7 C6 C5 123.6(15) . . ? C8 O3 Cd1 91.1(8) . 7_655 ? C1 O1' Cd1 85.3(12) . . ? C1 O2' Cd1 93(3) . . ? C5' C4' C3 110(3) . . ? C4' C5' C9 130(5) . . ? C4' C5' C6' 127(3) . . ? C9 C5' C6' 101(3) . . ? C7 C6' C5' 109(3) . . ? C8 O3' O4 45.0(9) . . ? C8 O3' Cd1 87.5(13) . 7_655 ? O4 O3' Cd1 67.7(10) . 7_655 ? O4' O4 C8 61.5(19) . . ? O4' O4 O3' 98(2) . . ? C8 O4 O3' 45.2(13) . . ? O4' O4 Cd1 80(2) . 7_655 ? C8 O4 Cd1 89.7(10) . 7_655 ? O3' O4 Cd1 70.6(11) . 7_655 ? O4 O4' C8 79(2) . . ? O4 O4' Cd1 81(2) . 7_655 ? C8 O4' Cd1 93.6(12) . 7_655 ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.719 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.085 #================================