# 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_global data_1 #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Cd N6 O3, 2(O)' _chemical_formula_sum 'C14 H9 Cd N6 O5' _chemical_formula_weight 453.67 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 'P 21/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 10.2783(7) _cell_length_b 9.3993(7) _cell_length_c 17.5516(12) _cell_angle_alpha 90.00 _cell_angle_beta 103.0550(10) _cell_angle_gamma 90.00 _cell_volume 1651.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7678 _cell_measurement_theta_min 2.382 _cell_measurement_theta_max 27.614 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 1.363 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7269 _exptl_absorpt_correction_T_max 0.7915 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker Smart Apex CCD ' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10861 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.64 _reflns_number_total 3814 _reflns_number_gt 3468 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0789P)^2^+1.2011P] 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 3814 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.77405(2) 0.838954(19) 0.249801(9) 0.02867(10) Uani 1 1 d . . . C1 C 1.1149(3) 0.6549(2) 0.35997(16) 0.0269(5) Uani 1 1 d . . . C2 C 1.1582(3) 0.7841(3) 0.39423(16) 0.0349(6) Uani 1 1 d . . . H2 H 1.1533 0.8657 0.3638 0.042 Uiso 1 1 calc R . . C3 C 1.2094(3) 0.7909(3) 0.47484(17) 0.0387(6) Uani 1 1 d . . . H3 H 1.2382 0.8776 0.4982 0.046 Uiso 1 1 calc R . . C4 C 1.2176(3) 0.6693(3) 0.52040(17) 0.0342(6) Uani 1 1 d . . . H4 H 1.2525 0.6750 0.5740 0.041 Uiso 1 1 calc R . . C5 C 1.1740(3) 0.5384(3) 0.48645(14) 0.0257(5) Uani 1 1 d . . . C6 C 1.1223(3) 0.5329(3) 0.40602(14) 0.0266(5) Uani 1 1 d . . . H6 H 1.0923 0.4465 0.3826 0.032 Uiso 1 1 calc R . . C7 C 1.0670(3) 0.6438(3) 0.27436(16) 0.0275(5) Uani 1 1 d . . . C8 C 1.1819(2) 0.4106(3) 0.53465(14) 0.0262(5) Uani 1 1 d . . . C9 C 1.2249(3) 0.3891(3) 0.61339(15) 0.0322(5) Uani 1 1 d . . . H9 H 1.2613 0.4589 0.6495 0.039 Uiso 1 1 calc R . . C10 C 1.1520(3) 0.1874(3) 0.56425(16) 0.0331(6) Uani 1 1 d . . . H10 H 1.1277 0.0920 0.5589 0.040 Uiso 1 1 calc R . . C11 C 0.5553(3) 0.6320(3) -0.00871(17) 0.0361(6) Uani 1 1 d . . . H11 H 0.5924 0.7204 -0.0146 0.043 Uiso 1 1 calc R . . C12 C 0.5622(3) 0.5772(3) 0.06586(15) 0.0327(5) Uani 1 1 d . . . C13 C 0.5068(3) 0.4453(3) 0.07403(16) 0.0380(6) Uani 1 1 d . . . H13 H 0.5114 0.4083 0.1237 0.046 Uiso 1 1 calc R . . C14 C 0.6319(4) 0.6603(3) 0.13653(19) 0.0387(7) Uani 1 1 d . . . N1 N 1.1151(3) 0.5489(2) 0.23066(13) 0.0311(5) Uani 1 1 d . . . N2 N 1.0553(3) 0.5787(3) 0.15549(13) 0.0368(5) Uani 1 1 d . . . N3 N 0.9757(3) 0.6851(3) 0.15481(14) 0.0391(6) Uani 1 1 d . . . N4 N 0.9796(3) 0.7290(2) 0.22921(13) 0.0348(5) Uani 1 1 d . . . N5 N 1.1362(2) 0.2796(2) 0.50477(12) 0.0301(5) Uani 1 1 d . . . H5 H 1.1032 0.2604 0.4563 0.036 Uiso 1 1 calc R . . N6 N 1.2065(2) 0.2489(3) 0.63149(13) 0.0313(5) Uani 1 1 d . . . O1 O 0.6774(2) 0.7816(2) 0.12605(12) 0.0421(5) Uani 1 1 d . . . O2 O 0.6405(4) 0.6101(3) 0.20256(14) 0.0783(11) Uani 1 1 d . . . O3 O 0.5706(4) 0.9770(5) 0.2357(2) 0.0846(11) Uani 1 1 d . . . O4 O 0.5395(5) 0.0407(7) 0.0806(4) 0.154(3) Uani 1 1 d . . . O5 O 0.3406(12) 0.7992(11) 0.2290(5) 0.227(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 Cd1 0.04186(16) 0.02624(14) 0.01499(13) -0.00134(5) 0.00034(9) -0.00862(7) C1 0.0308(12) 0.0275(13) 0.0202(12) 0.0029(8) 0.0008(10) 0.0039(9) C2 0.0461(15) 0.0254(12) 0.0297(13) 0.0014(10) 0.0013(12) 0.0014(11) C3 0.0514(17) 0.0288(13) 0.0303(14) -0.0052(12) -0.0027(12) -0.0038(13) C4 0.0431(16) 0.0349(15) 0.0205(12) -0.0045(9) -0.0014(12) -0.0033(11) C5 0.0288(11) 0.0284(12) 0.0185(10) 0.0011(9) 0.0025(9) 0.0009(9) C6 0.0333(12) 0.0243(11) 0.0194(11) 0.0001(9) 0.0002(9) 0.0006(9) C7 0.0366(13) 0.0232(11) 0.0208(12) 0.0023(9) 0.0025(10) 0.0034(9) C8 0.0281(11) 0.0313(12) 0.0177(11) -0.0002(9) 0.0019(9) -0.0029(9) C9 0.0416(14) 0.0332(13) 0.0184(11) -0.0007(10) -0.0004(10) -0.0074(12) C10 0.0451(15) 0.0317(12) 0.0205(12) 0.0019(10) 0.0037(11) -0.0067(12) C11 0.0433(15) 0.0336(13) 0.0285(14) -0.0043(11) 0.0018(12) -0.0089(12) C12 0.0345(13) 0.0378(14) 0.0223(11) -0.0101(10) -0.0009(10) -0.0059(11) C13 0.0476(16) 0.0423(15) 0.0199(11) -0.0025(10) -0.0012(11) -0.0088(13) C14 0.0423(16) 0.0454(18) 0.0250(14) -0.0109(11) 0.0007(12) -0.0112(12) N1 0.0444(13) 0.0268(11) 0.0198(10) 0.0033(8) 0.0026(9) 0.0089(9) N2 0.0573(15) 0.0296(11) 0.0213(10) 0.0033(9) 0.0044(10) 0.0112(11) N3 0.0592(17) 0.0360(12) 0.0193(11) 0.0027(9) 0.0025(11) 0.0160(12) N4 0.0507(14) 0.0330(12) 0.0183(9) 0.0029(9) 0.0027(9) 0.0133(10) N5 0.0418(12) 0.0318(11) 0.0138(9) -0.0010(8) 0.0006(8) -0.0072(10) N6 0.0396(12) 0.0345(12) 0.0185(10) 0.0023(8) 0.0036(9) -0.0077(9) O1 0.0488(12) 0.0436(12) 0.0290(10) -0.0124(9) -0.0012(9) -0.0143(10) O2 0.124(3) 0.0750(19) 0.0243(11) -0.0069(12) -0.0085(14) -0.050(2) O3 0.072(2) 0.119(3) 0.065(2) 0.0050(19) 0.0184(17) 0.032(2) O4 0.099(4) 0.215(7) 0.157(5) 0.093(5) 0.043(4) 0.047(4) O5 0.228(11) 0.288(10) 0.135(6) 0.054(6) -0.021(7) -0.105(9) _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 N6 2.208(2) 3_766 ? Cd1 O1 2.241(2) . ? Cd1 N1 2.266(2) 2_755 ? Cd1 O3 2.426(3) . ? Cd1 N4 2.451(3) . ? C1 C2 1.383(4) . ? C1 C6 1.395(3) . ? C1 C7 1.475(4) . ? C2 C3 1.395(4) . ? C2 H2 0.9300 . ? C3 C4 1.387(4) . ? C3 H3 0.9300 . ? C4 C5 1.396(4) . ? C4 H4 0.9300 . ? C5 C6 1.393(3) . ? C5 C8 1.461(3) . ? C6 H6 0.9300 . ? C7 N4 1.325(3) . ? C7 N1 1.341(3) . ? C8 C9 1.368(3) . ? C8 N5 1.379(3) . ? C9 N6 1.378(4) . ? C9 H9 0.9300 . ? C10 N6 1.320(4) . ? C10 N5 1.338(3) . ? C10 H10 0.9300 . ? C11 C13 1.385(4) 3_665 ? C11 C12 1.393(4) . ? C11 H11 0.9300 . ? C12 C13 1.385(4) . ? C12 C14 1.504(4) . ? C13 C11 1.385(4) 3_665 ? C13 H13 0.9300 . ? C14 O2 1.236(4) . ? C14 O1 1.261(4) . ? N1 N2 1.353(3) . ? N1 Cd1 2.266(2) 2_745 ? N2 N3 1.290(4) . ? N3 N4 1.361(3) . ? N5 H5 0.8600 . ? N6 Cd1 2.208(2) 3_766 ? 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 N6 Cd1 O1 138.64(9) 3_766 . ? N6 Cd1 N1 104.34(8) 3_766 2_755 ? O1 Cd1 N1 117.00(8) . 2_755 ? N6 Cd1 O3 100.87(11) 3_766 . ? O1 Cd1 O3 81.17(11) . . ? N1 Cd1 O3 86.68(13) 2_755 . ? N6 Cd1 N4 94.82(8) 3_766 . ? O1 Cd1 N4 87.93(8) . . ? N1 Cd1 N4 88.22(9) 2_755 . ? O3 Cd1 N4 164.26(10) . . ? C2 C1 C6 120.0(3) . . ? C2 C1 C7 120.4(2) . . ? C6 C1 C7 119.6(2) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 118.5(2) . . ? C6 C5 C8 121.0(2) . . ? C4 C5 C8 120.5(2) . . ? C5 C6 C1 121.0(2) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? N4 C7 N1 110.3(2) . . ? N4 C7 C1 126.3(2) . . ? N1 C7 C1 123.3(2) . . ? C9 C8 N5 104.9(2) . . ? C9 C8 C5 132.1(2) . . ? N5 C8 C5 123.0(2) . . ? C8 C9 N6 110.2(2) . . ? C8 C9 H9 124.9 . . ? N6 C9 H9 124.9 . . ? N6 C10 N5 111.5(2) . . ? N6 C10 H10 124.3 . . ? N5 C10 H10 124.3 . . ? C13 C11 C12 120.0(3) 3_665 . ? C13 C11 H11 120.0 3_665 . ? C12 C11 H11 120.0 . . ? C13 C12 C11 119.6(2) . . ? C13 C12 C14 120.7(3) . . ? C11 C12 C14 119.8(3) . . ? C11 C13 C12 120.4(3) 3_665 . ? C11 C13 H13 119.8 3_665 . ? C12 C13 H13 119.8 . . ? O2 C14 O1 122.1(3) . . ? O2 C14 C12 119.7(3) . . ? O1 C14 C12 118.2(3) . . ? C7 N1 N2 105.9(2) . . ? C7 N1 Cd1 136.90(17) . 2_745 ? N2 N1 Cd1 115.50(16) . 2_745 ? N3 N2 N1 108.5(2) . . ? N2 N3 N4 110.2(2) . . ? C7 N4 N3 105.1(2) . . ? C7 N4 Cd1 131.11(18) . . ? N3 N4 Cd1 115.45(19) . . ? C10 N5 C8 108.1(2) . . ? C10 N5 H5 125.9 . . ? C8 N5 H5 125.9 . . ? C10 N6 C9 105.4(2) . . ? C10 N6 Cd1 127.55(19) . 3_766 ? C9 N6 Cd1 125.96(17) . 3_766 ? C14 O1 Cd1 100.01(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.1(5) . . . . ? C7 C1 C2 C3 -176.8(3) . . . . ? C1 C2 C3 C4 0.4(5) . . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? C3 C4 C5 C6 0.0(5) . . . . ? C3 C4 C5 C8 -179.6(3) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? C8 C5 C6 C1 -180.0(2) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? C7 C1 C6 C5 176.4(3) . . . . ? C2 C1 C7 N4 -48.5(4) . . . . ? C6 C1 C7 N4 134.6(3) . . . . ? C2 C1 C7 N1 126.7(3) . . . . ? C6 C1 C7 N1 -50.2(4) . . . . ? C6 C5 C8 C9 -178.4(3) . . . . ? C4 C5 C8 C9 1.2(5) . . . . ? C6 C5 C8 N5 -1.9(4) . . . . ? C4 C5 C8 N5 177.7(3) . . . . ? N5 C8 C9 N6 0.1(3) . . . . ? C5 C8 C9 N6 177.1(3) . . . . ? C13 C11 C12 C13 0.1(5) 3_665 . . . ? C13 C11 C12 C14 178.9(3) 3_665 . . . ? C11 C12 C13 C11 -0.1(5) . . . 3_665 ? C14 C12 C13 C11 -178.9(3) . . . 3_665 ? C13 C12 C14 O2 0.4(5) . . . . ? C11 C12 C14 O2 -178.4(4) . . . . ? C13 C12 C14 O1 -178.1(3) . . . . ? C11 C12 C14 O1 3.1(5) . . . . ? N4 C7 N1 N2 0.7(3) . . . . ? C1 C7 N1 N2 -175.2(3) . . . . ? N4 C7 N1 Cd1 -163.2(2) . . . 2_745 ? C1 C7 N1 Cd1 21.0(5) . . . 2_745 ? C7 N1 N2 N3 -0.2(3) . . . . ? Cd1 N1 N2 N3 167.6(2) 2_745 . . . ? N1 N2 N3 N4 -0.3(4) . . . . ? N1 C7 N4 N3 -0.8(3) . . . . ? C1 C7 N4 N3 174.9(3) . . . . ? N1 C7 N4 Cd1 144.8(2) . . . . ? C1 C7 N4 Cd1 -39.5(4) . . . . ? N2 N3 N4 C7 0.7(4) . . . . ? N2 N3 N4 Cd1 -151.2(2) . . . . ? N6 Cd1 N4 C7 1.7(3) 3_766 . . . ? O1 Cd1 N4 C7 -137.0(3) . . . . ? N1 Cd1 N4 C7 105.9(3) 2_755 . . . ? O3 Cd1 N4 C7 177.0(4) . . . . ? N6 Cd1 N4 N3 144.5(2) 3_766 . . . ? O1 Cd1 N4 N3 5.9(2) . . . . ? N1 Cd1 N4 N3 -111.2(2) 2_755 . . . ? O3 Cd1 N4 N3 -40.1(5) . . . . ? N6 C10 N5 C8 -0.6(4) . . . . ? C9 C8 N5 C10 0.3(3) . . . . ? C5 C8 N5 C10 -177.0(3) . . . . ? N5 C10 N6 C9 0.7(3) . . . . ? N5 C10 N6 Cd1 169.1(2) . . . 3_766 ? C8 C9 N6 C10 -0.5(3) . . . . ? C8 C9 N6 Cd1 -169.18(19) . . . 3_766 ? O2 C14 O1 Cd1 4.3(4) . . . . ? C12 C14 O1 Cd1 -177.2(3) . . . . ? N6 Cd1 O1 C14 -4.5(3) 3_766 . . . ? N1 Cd1 O1 C14 177.3(2) 2_755 . . . ? O3 Cd1 O1 C14 -101.0(2) . . . . ? N4 Cd1 O1 C14 90.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.64 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.861 _refine_diff_density_min -0.856 _refine_diff_density_rms 0.143 _database_code_depnum_ccdc_archive 'CCDC 920971' ####################################################################### # # 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_global # Attachment '2.cif' # Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry data_2 #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H7 Cd N8 O3, 3(O)' _chemical_formula_sum 'C14 H9 Cd N6 O6' _chemical_formula_weight 469.67 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 'C 2/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 23.6066(15) _cell_length_b 10.0599(6) _cell_length_c 17.7135(11) _cell_angle_alpha 90.00 _cell_angle_beta 124.8360(10) _cell_angle_gamma 90.00 _cell_volume 3452.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7959 _cell_measurement_theta_min 3.122 _cell_measurement_theta_max 27.553 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1848 _exptl_absorpt_coefficient_mu 1.311 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7982 _exptl_absorpt_correction_T_max 0.8276 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker Smart Apex CCD ' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10561 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 27.55 _reflns_number_total 3852 _reflns_number_gt 3594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1241P)^2^+3.4150P] 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 3852 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.1440 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 0.364315(10) 0.40064(2) 0.373672(13) 0.02323(15) Uani 1 1 d . . . C1 C 0.20208(14) 0.6268(3) 0.31425(19) 0.0230(5) Uani 1 1 d . . . C2 C 0.19133(14) 0.7453(3) 0.34530(18) 0.0234(5) Uani 1 1 d . . . H2 H 0.2002 0.8259 0.3283 0.028 Uiso 1 1 calc R . . C3 C 0.16744(15) 0.7445(3) 0.40163(19) 0.0244(5) Uani 1 1 d . . . C4 C 0.15564(19) 0.6229(4) 0.4272(2) 0.0329(7) Uani 1 1 d . . . H4 H 0.1403 0.6204 0.4653 0.039 Uiso 1 1 calc R . . C5 C 0.1664(2) 0.5046(3) 0.3965(3) 0.0371(7) Uani 1 1 d . . . H5 H 0.1580 0.4240 0.4140 0.044 Uiso 1 1 calc R . . C6 C 0.18964(16) 0.5057(3) 0.3403(2) 0.0316(6) Uani 1 1 d . . . H6 H 0.1969 0.4262 0.3201 0.038 Uiso 1 1 calc R . . C7 C 0.22583(15) 0.6287(3) 0.25318(19) 0.0230(5) Uani 1 1 d . . . C8 C 0.15617(14) 0.8673(3) 0.43497(18) 0.0238(5) Uani 1 1 d . . . C9 C 0.13683(18) 0.8872(3) 0.4939(2) 0.0288(6) Uani 1 1 d . . . H9 H 0.1251 0.8202 0.5188 0.035 Uiso 1 1 calc R . . C10 C 0.15679(18) 1.0815(3) 0.4622(2) 0.0291(6) Uani 1 1 d . . . H10 H 0.1616 1.1730 0.4606 0.035 Uiso 1 1 calc R . . C11 C 0.5000 0.8281(5) 0.2500 0.0459(12) Uani 1 2 d S . . H11 H 0.5000 0.9205 0.2500 0.055 Uiso 1 2 calc SR . . C12 C 0.47221(18) 0.7586(3) 0.2897(2) 0.0356(7) Uani 1 1 d . . . H12 H 0.4539 0.8047 0.3166 0.043 Uiso 1 1 calc R . . C13 C 0.47188(15) 0.6217(3) 0.2892(2) 0.0259(6) Uani 1 1 d . . . C14 C 0.5000 0.5519(4) 0.2500 0.0256(8) Uani 1 2 d S . . H14 H 0.5000 0.4594 0.2500 0.031 Uiso 1 2 calc SR . . C15 C 0.43980(14) 0.5469(3) 0.32939(19) 0.0278(6) Uani 1 1 d . . . N1 N 0.26972(13) 0.5427(3) 0.25499(18) 0.0283(5) Uani 1 1 d . . . N2 N 0.27484(16) 0.5805(3) 0.1863(2) 0.0325(6) Uani 1 1 d . . . N3 N 0.23640(15) 0.6843(3) 0.14457(19) 0.0323(6) Uani 1 1 d . . . N4 N 0.20467(13) 0.7181(3) 0.18633(17) 0.0267(5) Uani 1 1 d . . . N5 N 0.16839(13) 0.9929(3) 0.41569(17) 0.0279(5) Uani 1 1 d . . . H5A H 0.1812 1.0112 0.3801 0.034 Uiso 1 1 calc R . . N6 N 0.13740(13) 1.0208(3) 0.51080(16) 0.0274(5) Uani 1 1 d . . . O1 O 0.43057(16) 0.6055(2) 0.3847(2) 0.0378(6) Uani 1 1 d . . . O2 O 0.42023(13) 0.4298(3) 0.30396(18) 0.0333(5) Uani 1 1 d . . . O3 O 0.45774(16) 0.2599(3) 0.4727(2) 0.0570(8) Uani 1 1 d . . . O4 O 0.4837(2) 0.1662(6) 0.3195(4) 0.1051(18) Uani 1 1 d . . . O5 O 0.1358(3) 0.3611(10) 0.1281(5) 0.130(3) Uani 1 1 d . . . O6 O 0.0462(6) 0.5066(10) 0.9767(6) 0.214(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 Cd1 0.0294(2) 0.0234(2) 0.02552(19) -0.00439(6) 0.02082(15) -0.00439(6) C1 0.0231(12) 0.0261(13) 0.0233(12) -0.0009(11) 0.0152(11) 0.0025(11) C2 0.0265(12) 0.0235(13) 0.0229(12) 0.0008(10) 0.0158(11) 0.0022(10) C3 0.0250(12) 0.0271(14) 0.0225(11) -0.0004(10) 0.0143(10) 0.0030(11) C4 0.0422(18) 0.0343(16) 0.0380(17) 0.0017(13) 0.0323(15) 0.0006(13) C5 0.0517(19) 0.0250(15) 0.0502(18) 0.0027(14) 0.0383(16) -0.0016(14) C6 0.0401(16) 0.0234(14) 0.0399(16) -0.0001(12) 0.0279(14) 0.0020(12) C7 0.0254(13) 0.0212(12) 0.0241(12) -0.0034(11) 0.0151(11) 0.0015(11) C8 0.0274(13) 0.0277(13) 0.0207(12) -0.0001(11) 0.0163(11) 0.0006(11) C9 0.0385(17) 0.0284(15) 0.0299(15) -0.0009(11) 0.0255(14) -0.0024(11) C10 0.0396(17) 0.0271(14) 0.0293(15) 0.0008(11) 0.0249(14) 0.0022(11) C11 0.069(3) 0.025(2) 0.071(3) 0.000 0.057(3) 0.000 C12 0.0459(18) 0.0316(16) 0.0459(17) -0.0039(13) 0.0360(16) 0.0015(13) C13 0.0251(13) 0.0322(14) 0.0266(13) -0.0014(11) 0.0184(12) -0.0034(11) C14 0.0265(18) 0.027(2) 0.0298(18) 0.000 0.0201(16) 0.000 C15 0.0223(12) 0.0388(17) 0.0266(12) 0.0000(12) 0.0165(11) -0.0030(11) N1 0.0360(13) 0.0270(13) 0.0304(12) 0.0029(10) 0.0240(11) 0.0072(11) N2 0.0402(15) 0.0315(13) 0.0365(14) 0.0033(11) 0.0282(13) 0.0076(11) N3 0.0439(14) 0.0310(14) 0.0344(12) 0.0051(10) 0.0297(12) 0.0092(11) N4 0.0342(12) 0.0253(12) 0.0281(11) 0.0024(9) 0.0222(10) 0.0066(10) N5 0.0372(12) 0.0304(13) 0.0278(11) 0.0026(10) 0.0253(10) 0.0030(10) N6 0.0373(13) 0.0283(13) 0.0263(11) -0.0027(9) 0.0239(10) 0.0009(10) O1 0.0454(15) 0.0468(16) 0.0404(14) -0.0114(10) 0.0359(13) -0.0114(10) O2 0.0382(12) 0.0337(11) 0.0427(13) -0.0041(10) 0.0317(11) -0.0054(10) O3 0.0495(16) 0.0410(15) 0.0476(15) -0.0050(13) 0.0084(13) 0.0062(12) O4 0.067(2) 0.108(4) 0.108(4) -0.028(3) 0.030(2) 0.026(3) O5 0.125(6) 0.149(6) 0.134(7) -0.052(4) 0.084(5) -0.040(4) O6 0.335(13) 0.176(8) 0.162(8) 0.015(7) 0.161(9) 0.116(9) _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 N6 2.216(2) 7_566 ? Cd1 N4 2.275(2) 4_545 ? Cd1 O2 2.284(2) . ? Cd1 O3 2.351(3) . ? Cd1 N1 2.467(3) . ? Cd1 O1 2.527(2) . ? C1 C6 1.393(4) . ? C1 C2 1.395(4) . ? C1 C7 1.476(4) . ? C2 C3 1.399(4) . ? C2 H2 0.9300 . ? C3 C4 1.387(5) . ? C3 C8 1.457(4) . ? C4 C5 1.390(5) . ? C4 H4 0.9300 . ? C5 C6 1.384(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N4 1.336(4) . ? C7 N1 1.336(4) . ? C8 C9 1.373(4) . ? C8 N5 1.382(4) . ? C9 N6 1.375(4) . ? C9 H9 0.9300 . ? C10 N6 1.332(4) . ? C10 N5 1.343(4) . ? C10 H10 0.9300 . ? C11 C12 1.393(4) 2_655 ? C11 C12 1.393(4) . ? C11 H11 0.9300 . ? C12 C13 1.378(5) . ? C12 H12 0.9300 . ? C13 C14 1.394(4) . ? C13 C15 1.503(4) . ? C14 C13 1.394(4) 2_655 ? C14 H14 0.9300 . ? C15 O2 1.252(4) . ? C15 O1 1.264(4) . ? N1 N2 1.345(4) . ? N2 N3 1.302(4) . ? N3 N4 1.362(3) . ? N4 Cd1 2.275(2) 4 ? N5 H5A 0.8600 . ? N6 Cd1 2.216(2) 7_566 ? 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 N6 Cd1 N4 109.48(9) 7_566 4_545 ? N6 Cd1 O2 140.78(9) 7_566 . ? N4 Cd1 O2 109.38(9) 4_545 . ? N6 Cd1 O3 91.72(11) 7_566 . ? N4 Cd1 O3 88.77(10) 4_545 . ? O2 Cd1 O3 83.99(12) . . ? N6 Cd1 N1 95.46(9) 7_566 . ? N4 Cd1 N1 90.66(9) 4_545 . ? O2 Cd1 N1 89.20(9) . . ? O3 Cd1 N1 172.56(11) . . ? N6 Cd1 O1 88.56(9) 7_566 . ? N4 Cd1 O1 160.19(9) 4_545 . ? O2 Cd1 O1 54.07(8) . . ? O3 Cd1 O1 99.11(11) . . ? N1 Cd1 O1 79.18(9) . . ? C6 C1 C2 119.8(3) . . ? C6 C1 C7 119.6(3) . . ? C2 C1 C7 120.6(3) . . ? C1 C2 C3 121.0(3) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 118.4(3) . . ? C4 C3 C8 119.9(3) . . ? C2 C3 C8 121.7(3) . . ? C3 C4 C5 120.8(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 119.3(3) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? N4 C7 N1 110.4(2) . . ? N4 C7 C1 123.5(3) . . ? N1 C7 C1 126.0(3) . . ? C9 C8 N5 105.2(3) . . ? C9 C8 C3 130.5(3) . . ? N5 C8 C3 124.2(2) . . ? C8 C9 N6 110.0(3) . . ? C8 C9 H9 125.0 . . ? N6 C9 H9 125.0 . . ? N6 C10 N5 111.0(3) . . ? N6 C10 H10 124.5 . . ? N5 C10 H10 124.5 . . ? C12 C11 C12 119.8(5) 2_655 . ? C12 C11 H11 120.1 2_655 . ? C12 C11 H11 120.1 . . ? C13 C12 C11 120.1(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.3(3) . . ? C12 C13 C15 120.0(3) . . ? C14 C13 C15 119.7(3) . . ? C13 C14 C13 119.5(4) 2_655 . ? C13 C14 H14 120.2 2_655 . ? C13 C14 H14 120.2 . . ? O2 C15 O1 121.7(3) . . ? O2 C15 C13 118.9(3) . . ? O1 C15 C13 119.3(3) . . ? C7 N1 N2 105.4(2) . . ? C7 N1 Cd1 135.04(19) . . ? N2 N1 Cd1 115.43(19) . . ? N3 N2 N1 110.3(3) . . ? N2 N3 N4 108.2(2) . . ? C7 N4 N3 105.7(2) . . ? C7 N4 Cd1 139.7(2) . 4 ? N3 N4 Cd1 114.62(18) . 4 ? C10 N5 C8 108.1(2) . . ? C10 N5 H5A 125.9 . . ? C8 N5 H5A 125.9 . . ? C10 N6 C9 105.8(2) . . ? C10 N6 Cd1 128.9(2) . 7_566 ? C9 N6 Cd1 123.1(2) . 7_566 ? C15 O1 Cd1 86.16(18) . . ? C15 O2 Cd1 97.76(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.7(4) . . . . ? C7 C1 C2 C3 178.6(3) . . . . ? C1 C2 C3 C4 1.0(4) . . . . ? C1 C2 C3 C8 179.8(3) . . . . ? C2 C3 C4 C5 -0.8(5) . . . . ? C8 C3 C4 C5 -179.7(3) . . . . ? C3 C4 C5 C6 0.4(6) . . . . ? C4 C5 C6 C1 -0.1(5) . . . . ? C2 C1 C6 C5 0.3(5) . . . . ? C7 C1 C6 C5 -179.1(3) . . . . ? C6 C1 C7 N4 141.5(3) . . . . ? C2 C1 C7 N4 -37.9(4) . . . . ? C6 C1 C7 N1 -37.4(4) . . . . ? C2 C1 C7 N1 143.2(3) . . . . ? C4 C3 C8 C9 2.7(5) . . . . ? C2 C3 C8 C9 -176.1(3) . . . . ? C4 C3 C8 N5 178.0(3) . . . . ? C2 C3 C8 N5 -0.8(4) . . . . ? N5 C8 C9 N6 -0.3(4) . . . . ? C3 C8 C9 N6 175.7(3) . . . . ? C12 C11 C12 C13 -0.4(2) 2_655 . . . ? C11 C12 C13 C14 0.8(5) . . . . ? C11 C12 C13 C15 -178.0(2) . . . . ? C12 C13 C14 C13 -0.4(2) . . . 2_655 ? C15 C13 C14 C13 178.4(3) . . . 2_655 ? C12 C13 C15 O2 157.7(3) . . . . ? C14 C13 C15 O2 -21.1(4) . . . . ? C12 C13 C15 O1 -19.2(5) . . . . ? C14 C13 C15 O1 162.0(3) . . . . ? N4 C7 N1 N2 -0.6(3) . . . . ? C1 C7 N1 N2 178.4(3) . . . . ? N4 C7 N1 Cd1 154.2(2) . . . . ? C1 C7 N1 Cd1 -26.7(5) . . . . ? N6 Cd1 N1 C7 -6.2(3) 7_566 . . . ? N4 Cd1 N1 C7 103.5(3) 4_545 . . . ? O2 Cd1 N1 C7 -147.1(3) . . . . ? O1 Cd1 N1 C7 -93.6(3) . . . . ? N6 Cd1 N1 N2 146.9(2) 7_566 . . . ? N4 Cd1 N1 N2 -103.5(2) 4_545 . . . ? O2 Cd1 N1 N2 5.9(2) . . . . ? O1 Cd1 N1 N2 59.4(2) . . . . ? C7 N1 N2 N3 0.2(4) . . . . ? Cd1 N1 N2 N3 -160.4(2) . . . . ? N1 N2 N3 N4 0.3(4) . . . . ? N1 C7 N4 N3 0.8(3) . . . . ? C1 C7 N4 N3 -178.3(3) . . . . ? N1 C7 N4 Cd1 -178.7(2) . . . 4 ? C1 C7 N4 Cd1 2.3(5) . . . 4 ? N2 N3 N4 C7 -0.6(3) . . . . ? N2 N3 N4 Cd1 179.0(2) . . . 4 ? N6 C10 N5 C8 -0.2(4) . . . . ? C9 C8 N5 C10 0.3(3) . . . . ? C3 C8 N5 C10 -176.0(3) . . . . ? N5 C10 N6 C9 0.0(4) . . . . ? N5 C10 N6 Cd1 163.2(2) . . . 7_566 ? C8 C9 N6 C10 0.2(4) . . . . ? C8 C9 N6 Cd1 -164.3(2) . . . 7_566 ? O2 C15 O1 Cd1 -5.0(3) . . . . ? C13 C15 O1 Cd1 171.9(2) . . . . ? N6 Cd1 O1 C15 170.1(2) 7_566 . . . ? N4 Cd1 O1 C15 -33.8(4) 4_545 . . . ? O2 Cd1 O1 C15 2.85(18) . . . . ? O3 Cd1 O1 C15 78.5(2) . . . . ? N1 Cd1 O1 C15 -94.1(2) . . . . ? O1 C15 O2 Cd1 5.5(3) . . . . ? C13 C15 O2 Cd1 -171.3(2) . . . . ? N6 Cd1 O2 C15 -23.4(3) 7_566 . . . ? N4 Cd1 O2 C15 164.71(19) 4_545 . . . ? O3 Cd1 O2 C15 -108.7(2) . . . . ? N1 Cd1 O2 C15 74.3(2) . . . . ? O1 Cd1 O2 C15 -2.90(18) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.111 _refine_diff_density_min -1.456 _refine_diff_density_rms 0.346 _database_code_depnum_ccdc_archive 'CCDC 920972' ####################################################################### # # 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_global # Attachment '3.cif' # Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry data_3 #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 Cd N6 O5' _chemical_formula_sum 'C19 H14 Cd N6 O5' _chemical_formula_weight 518.76 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 'P 21/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 6.9138(9) _cell_length_b 17.721(2) _cell_length_c 15.812(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.216(2) _cell_angle_gamma 90.00 _cell_volume 1906.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8349 _cell_measurement_theta_min 2.617 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 1.193 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7627 _exptl_absorpt_correction_T_max 0.8320 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker Smart Apex CCD ' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12596 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4340 _reflns_number_gt 4009 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0691P)^2^+0.9222P] 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 4340 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.67036(2) 0.396642(9) 0.656613(10) 0.01998(8) Uani 1 1 d . . . C1 C 1.1776(3) 0.29865(12) 0.72264(15) 0.0211(4) Uani 1 1 d . . . C2 C 1.3011(3) 0.23961(14) 0.70823(17) 0.0271(5) Uani 1 1 d . . . H2 H 1.3930 0.2467 0.6726 0.032 Uiso 1 1 calc R . . C3 C 1.2863(4) 0.17019(14) 0.74734(17) 0.0285(5) Uani 1 1 d . . . H3 H 1.3701 0.1311 0.7384 0.034 Uiso 1 1 calc R . . C4 C 1.1476(4) 0.15853(13) 0.79975(16) 0.0257(5) Uani 1 1 d . . . H4 H 1.1371 0.1116 0.8248 0.031 Uiso 1 1 calc R . . C5 C 1.0240(3) 0.21748(13) 0.81465(14) 0.0209(4) Uani 1 1 d . . . C6 C 1.0418(3) 0.28754(12) 0.77702(15) 0.0214(4) Uani 1 1 d . . . H6 H 0.9624 0.3273 0.7882 0.026 Uiso 1 1 calc R . . C7 C 1.1759(3) 0.37056(13) 0.67671(15) 0.0198(4) Uani 1 1 d . . . C8 C 0.8676(4) 0.20589(12) 0.86537(15) 0.0227(4) Uani 1 1 d . . . C9 C 0.7694(4) 0.25390(15) 0.90940(18) 0.0345(6) Uani 1 1 d . . . H9 H 0.7903 0.3056 0.9157 0.041 Uiso 1 1 calc R . . C10 C 0.6442(4) 0.14135(14) 0.91915(17) 0.0288(5) Uani 1 1 d . . . H10 H 0.5669 0.1019 0.9331 0.035 Uiso 1 1 calc R . . C11 C 0.7534(3) 0.16150(12) 0.56122(15) 0.0213(4) Uani 1 1 d . . . C12 C 0.7575(4) 0.11529(13) 0.63218(15) 0.0219(4) Uani 1 1 d . . . H12 H 0.7550 0.1364 0.6858 0.026 Uiso 1 1 calc R . . C13 C 0.7653(3) 0.03681(13) 0.62318(15) 0.0222(4) Uani 1 1 d . . . C14 C 0.7595(4) 0.00594(13) 0.54184(16) 0.0255(5) Uani 1 1 d . . . H14 H 0.7601 -0.0462 0.5357 0.031 Uiso 1 1 calc R . . C15 C 0.7527(4) 0.05123(13) 0.46938(15) 0.0252(5) Uani 1 1 d . . . C16 C 0.7555(4) 0.12956(14) 0.48065(15) 0.0255(5) Uani 1 1 d . . . H16 H 0.7589 0.1609 0.4337 0.031 Uiso 1 1 calc R . . C17 C 0.7493(3) 0.24597(12) 0.56984(14) 0.0211(4) Uani 1 1 d . . . C18 C 0.7880(3) -0.01401(13) 0.70032(15) 0.0222(4) Uani 1 1 d . . . C19 C 0.7436(4) 0.01729(16) 0.38136(16) 0.0337(6) Uani 1 1 d . . . H19A H 0.7893 -0.0339 0.3869 0.051 Uiso 1 1 calc R . . H19B H 0.8253 0.0460 0.3500 0.051 Uiso 1 1 calc R . . H19C H 0.6104 0.0182 0.3511 0.051 Uiso 1 1 calc R . . N1 N 1.0134(3) 0.41384(12) 0.65698(14) 0.0236(4) Uani 1 1 d . . . N2 N 1.0661(3) 0.47364(11) 0.61334(14) 0.0276(4) Uani 1 1 d . . . N3 N 1.2513(3) 0.46659(11) 0.60679(14) 0.0277(4) Uani 1 1 d . . . H3A H 1.3160 0.4982 0.5813 0.033 Uiso 1 1 calc R . . N4 N 1.3263(3) 0.40231(10) 0.64598(15) 0.0230(4) Uani 1 1 d . . . N5 N 0.6337(3) 0.21254(13) 0.94294(15) 0.0340(5) Uani 1 1 d . . . H5 H 0.5545 0.2300 0.9744 0.041 Uiso 1 1 calc R . . N6 N 0.7834(3) 0.13601(11) 0.87206(13) 0.0251(4) Uani 1 1 d . . . O1 O 0.6827(2) 0.27264(9) 0.63286(11) 0.0249(3) Uani 1 1 d . . . O2 O 0.8095(3) 0.28544(10) 0.51328(12) 0.0335(4) Uani 1 1 d . . . O3 O 0.8114(3) 0.01440(9) 0.77482(11) 0.0280(4) Uani 1 1 d . . . O4 O 0.7868(3) -0.08435(10) 0.69021(12) 0.0297(4) Uani 1 1 d . . . O5 O 0.6273(3) 0.42338(11) 0.51081(12) 0.0304(4) 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 0.01962(12) 0.01794(12) 0.02362(12) -0.00198(5) 0.00724(7) -0.00021(5) C1 0.0196(10) 0.0207(10) 0.0232(10) 0.0020(8) 0.0043(8) -0.0009(8) C2 0.0221(11) 0.0265(11) 0.0359(13) 0.0023(10) 0.0139(9) 0.0015(9) C3 0.0280(12) 0.0222(11) 0.0374(13) 0.0015(9) 0.0115(10) 0.0062(9) C4 0.0271(12) 0.0206(11) 0.0299(12) 0.0045(9) 0.0065(10) 0.0012(9) C5 0.0214(10) 0.0231(10) 0.0189(10) 0.0018(8) 0.0055(8) -0.0012(8) C6 0.0218(10) 0.0210(10) 0.0220(10) 0.0016(8) 0.0058(8) 0.0017(8) C7 0.0176(10) 0.0208(11) 0.0219(10) 0.0002(9) 0.0063(8) -0.0014(8) C8 0.0286(11) 0.0191(10) 0.0221(10) 0.0018(9) 0.0087(9) -0.0019(9) C9 0.0458(16) 0.0217(11) 0.0422(15) -0.0040(11) 0.0249(13) -0.0054(10) C10 0.0318(13) 0.0260(12) 0.0306(13) 0.0028(10) 0.0106(10) -0.0051(9) C11 0.0225(11) 0.0186(10) 0.0238(11) 0.0010(8) 0.0063(8) 0.0026(8) C12 0.0256(11) 0.0190(10) 0.0217(11) -0.0006(8) 0.0062(9) 0.0008(8) C13 0.0239(11) 0.0183(10) 0.0247(11) 0.0018(9) 0.0053(9) -0.0002(8) C14 0.0290(12) 0.0197(10) 0.0284(12) -0.0018(9) 0.0068(9) 0.0017(9) C15 0.0280(12) 0.0259(11) 0.0219(11) -0.0039(9) 0.0047(9) 0.0025(9) C16 0.0314(12) 0.0238(11) 0.0222(11) 0.0023(9) 0.0068(9) 0.0025(9) C17 0.0220(10) 0.0188(10) 0.0238(11) 0.0016(8) 0.0074(8) 0.0012(8) C18 0.0198(10) 0.0213(10) 0.0266(11) 0.0017(9) 0.0078(8) -0.0004(8) C19 0.0399(14) 0.0364(14) 0.0242(12) -0.0072(10) 0.0039(10) 0.0029(11) N1 0.0210(10) 0.0214(9) 0.0299(11) 0.0043(8) 0.0088(8) -0.0001(8) N2 0.0250(10) 0.0231(10) 0.0364(11) 0.0076(8) 0.0097(8) 0.0015(8) N3 0.0260(10) 0.0223(9) 0.0373(11) 0.0096(8) 0.0122(9) -0.0008(8) N4 0.0204(10) 0.0219(10) 0.0286(11) 0.0043(7) 0.0093(8) -0.0007(7) N5 0.0405(12) 0.0301(11) 0.0376(12) -0.0030(9) 0.0237(10) -0.0024(9) N6 0.0293(10) 0.0204(9) 0.0273(10) 0.0021(8) 0.0094(8) -0.0011(8) O1 0.0311(9) 0.0184(8) 0.0286(8) -0.0006(6) 0.0144(7) -0.0002(6) O2 0.0478(11) 0.0216(8) 0.0380(10) 0.0062(7) 0.0268(9) 0.0038(7) O3 0.0426(10) 0.0194(8) 0.0234(8) 0.0011(6) 0.0100(7) 0.0010(7) O4 0.0433(11) 0.0169(8) 0.0305(9) 0.0012(7) 0.0111(8) -0.0013(7) O5 0.0336(10) 0.0322(10) 0.0265(9) 0.0058(8) 0.0087(7) -0.0001(8) _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 2.2336(16) . ? Cd1 O5 2.3206(18) . ? Cd1 O3 2.3447(16) 2_656 ? Cd1 N4 2.357(2) 1_455 ? Cd1 N1 2.390(2) . ? Cd1 O4 2.4110(19) 2_656 ? Cd1 C18 2.734(2) 2_656 ? C1 C2 1.394(3) . ? C1 C6 1.395(3) . ? C1 C7 1.466(3) . ? C2 C3 1.389(3) . ? C2 H2 0.9300 . ? C3 C4 1.390(3) . ? C3 H3 0.9300 . ? C4 C5 1.396(3) . ? C4 H4 0.9300 . ? C5 C6 1.392(3) . ? C5 C8 1.471(3) . ? C6 H6 0.9300 . ? C7 N4 1.346(3) . ? C7 N1 1.350(3) . ? C8 C9 1.356(3) . ? C8 N6 1.380(3) . ? C9 N5 1.369(3) . ? C9 H9 0.9300 . ? C10 N6 1.321(3) . ? C10 N5 1.322(3) . ? C10 H10 0.9300 . ? C11 C12 1.385(3) . ? C11 C16 1.397(3) . ? C11 C17 1.504(3) . ? C12 C13 1.400(3) . ? C12 H12 0.9300 . ? C13 C14 1.392(3) . ? C13 C18 1.502(3) . ? C14 C15 1.393(3) . ? C14 H14 0.9300 . ? C15 C16 1.399(3) . ? C15 C19 1.507(3) . ? C16 H16 0.9300 . ? C17 O1 1.261(3) . ? C17 O2 1.262(3) . ? C18 O4 1.257(3) . ? C18 O3 1.265(3) . ? C18 Cd1 2.734(2) 2_646 ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N1 N2 1.349(3) . ? N2 N3 1.309(3) . ? N3 N4 1.355(3) . ? N3 H3A 0.8600 . ? N4 Cd1 2.357(2) 1_655 ? N5 H5 0.8600 . ? O3 Cd1 2.3447(16) 2_646 ? O4 Cd1 2.4110(19) 2_646 ? 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 O5 92.05(7) . . ? O1 Cd1 O3 162.34(6) . 2_656 ? O5 Cd1 O3 105.34(6) . 2_656 ? O1 Cd1 N4 95.64(6) . 1_455 ? O5 Cd1 N4 88.31(7) . 1_455 ? O3 Cd1 N4 88.04(7) 2_656 1_455 ? O1 Cd1 N1 93.34(7) . . ? O5 Cd1 N1 85.91(7) . . ? O3 Cd1 N1 85.03(7) 2_656 . ? N4 Cd1 N1 169.49(7) 1_455 . ? O1 Cd1 O4 107.74(6) . 2_656 ? O5 Cd1 O4 160.19(7) . 2_656 ? O3 Cd1 O4 54.84(6) 2_656 2_656 ? N4 Cd1 O4 90.48(7) 1_455 2_656 ? N1 Cd1 O4 91.98(7) . 2_656 ? O1 Cd1 C18 135.01(7) . 2_656 ? O5 Cd1 C18 132.83(7) . 2_656 ? O3 Cd1 C18 27.49(6) 2_656 2_656 ? N4 Cd1 C18 89.49(7) 1_455 2_656 ? N1 Cd1 C18 88.01(7) . 2_656 ? O4 Cd1 C18 27.36(7) 2_656 2_656 ? C2 C1 C6 119.6(2) . . ? C2 C1 C7 121.5(2) . . ? C6 C1 C7 118.7(2) . . ? C3 C2 C1 119.8(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.7(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.8(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.5(2) . . ? C6 C5 C8 119.1(2) . . ? C4 C5 C8 121.3(2) . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N4 C7 N1 110.1(2) . . ? N4 C7 C1 127.1(2) . . ? N1 C7 C1 122.78(19) . . ? C9 C8 N6 105.5(2) . . ? C9 C8 C5 132.6(2) . . ? N6 C8 C5 121.9(2) . . ? C8 C9 N5 107.6(2) . . ? C8 C9 H9 126.2 . . ? N5 C9 H9 126.2 . . ? N6 C10 N5 108.1(2) . . ? N6 C10 H10 125.9 . . ? N5 C10 H10 125.9 . . ? C12 C11 C16 119.8(2) . . ? C12 C11 C17 120.9(2) . . ? C16 C11 C17 119.3(2) . . ? C11 C12 C13 120.0(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 119.3(2) . . ? C14 C13 C18 119.8(2) . . ? C12 C13 C18 120.9(2) . . ? C13 C14 C15 121.7(2) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C14 C15 C16 118.0(2) . . ? C14 C15 C19 121.3(2) . . ? C16 C15 C19 120.7(2) . . ? C11 C16 C15 121.1(2) . . ? C11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? O1 C17 O2 124.4(2) . . ? O1 C17 C11 117.37(19) . . ? O2 C17 C11 118.3(2) . . ? O4 C18 O3 120.7(2) . . ? O4 C18 C13 119.6(2) . . ? O3 C18 C13 119.7(2) . . ? O4 C18 Cd1 61.84(13) . 2_646 ? O3 C18 Cd1 58.84(12) . 2_646 ? C13 C18 Cd1 178.53(16) . 2_646 ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 N1 C7 105.98(18) . . ? N2 N1 Cd1 117.16(15) . . ? C7 N1 Cd1 135.46(16) . . ? N3 N2 N1 108.78(19) . . ? N2 N3 N4 110.15(19) . . ? N2 N3 H3A 124.9 . . ? N4 N3 H3A 124.9 . . ? C7 N4 N3 105.02(19) . . ? C7 N4 Cd1 142.24(16) . 1_655 ? N3 N4 Cd1 111.58(14) . 1_655 ? C10 N5 C9 108.9(2) . . ? C10 N5 H5 125.5 . . ? C9 N5 H5 125.5 . . ? C10 N6 C8 109.8(2) . . ? C17 O1 Cd1 122.12(14) . . ? C18 O3 Cd1 93.67(14) . 2_646 ? C18 O4 Cd1 90.80(15) . 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 C6 C1 C2 C3 0.7(4) . . . . ? C7 C1 C2 C3 -174.4(2) . . . . ? C1 C2 C3 C4 1.0(4) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C3 C4 C5 C8 176.2(2) . . . . ? C4 C5 C6 C1 1.9(3) . . . . ? C8 C5 C6 C1 -174.6(2) . . . . ? C2 C1 C6 C5 -2.1(4) . . . . ? C7 C1 C6 C5 173.1(2) . . . . ? C2 C1 C7 N4 -28.9(4) . . . . ? C6 C1 C7 N4 156.0(2) . . . . ? C2 C1 C7 N1 148.9(2) . . . . ? C6 C1 C7 N1 -26.2(3) . . . . ? C6 C5 C8 C9 -25.7(4) . . . . ? C4 C5 C8 C9 157.8(3) . . . . ? C6 C5 C8 N6 150.6(2) . . . . ? C4 C5 C8 N6 -25.8(4) . . . . ? N6 C8 C9 N5 1.4(3) . . . . ? C5 C8 C9 N5 178.2(3) . . . . ? C16 C11 C12 C13 0.5(4) . . . . ? C17 C11 C12 C13 -178.7(2) . . . . ? C11 C12 C13 C14 -3.0(4) . . . . ? C11 C12 C13 C18 174.5(2) . . . . ? C12 C13 C14 C15 2.2(4) . . . . ? C18 C13 C14 C15 -175.3(2) . . . . ? C13 C14 C15 C16 1.2(4) . . . . ? C13 C14 C15 C19 -179.1(2) . . . . ? C12 C11 C16 C15 3.0(4) . . . . ? C17 C11 C16 C15 -177.8(2) . . . . ? C14 C15 C16 C11 -3.7(4) . . . . ? C19 C15 C16 C11 176.6(2) . . . . ? C12 C11 C17 O1 -24.0(3) . . . . ? C16 C11 C17 O1 156.8(2) . . . . ? C12 C11 C17 O2 157.1(2) . . . . ? C16 C11 C17 O2 -22.1(3) . . . . ? C14 C13 C18 O4 -5.3(3) . . . . ? C12 C13 C18 O4 177.2(2) . . . . ? C14 C13 C18 O3 173.5(2) . . . . ? C12 C13 C18 O3 -4.0(3) . . . . ? N4 C7 N1 N2 -0.2(3) . . . . ? C1 C7 N1 N2 -178.4(2) . . . . ? N4 C7 N1 Cd1 165.24(19) . . . . ? C1 C7 N1 Cd1 -12.9(4) . . . . ? O1 Cd1 N1 N2 135.93(17) . . . . ? O5 Cd1 N1 N2 44.11(17) . . . . ? O3 Cd1 N1 N2 -61.71(17) 2_656 . . . ? N4 Cd1 N1 N2 -12.7(5) 1_455 . . . ? O4 Cd1 N1 N2 -116.16(17) 2_656 . . . ? C18 Cd1 N1 N2 -89.09(18) 2_656 . . . ? O1 Cd1 N1 C7 -28.3(2) . . . . ? O5 Cd1 N1 C7 -120.1(2) . . . . ? O3 Cd1 N1 C7 134.1(2) 2_656 . . . ? N4 Cd1 N1 C7 -176.9(3) 1_455 . . . ? O4 Cd1 N1 C7 79.6(2) 2_656 . . . ? C18 Cd1 N1 C7 106.7(2) 2_656 . . . ? C7 N1 N2 N3 0.2(3) . . . . ? Cd1 N1 N2 N3 -168.34(16) . . . . ? N1 N2 N3 N4 -0.2(3) . . . . ? N1 C7 N4 N3 0.1(3) . . . . ? C1 C7 N4 N3 178.1(2) . . . . ? N1 C7 N4 Cd1 165.6(2) . . . 1_655 ? C1 C7 N4 Cd1 -16.3(4) . . . 1_655 ? N2 N3 N4 C7 0.1(3) . . . . ? N2 N3 N4 Cd1 -170.47(16) . . . 1_655 ? N6 C10 N5 C9 0.5(3) . . . . ? C8 C9 N5 C10 -1.2(3) . . . . ? N5 C10 N6 C8 0.4(3) . . . . ? C9 C8 N6 C10 -1.2(3) . . . . ? C5 C8 N6 C10 -178.4(2) . . . . ? O2 C17 O1 Cd1 -2.1(3) . . . . ? C11 C17 O1 Cd1 179.02(15) . . . . ? O5 Cd1 O1 C17 30.79(18) . . . . ? O3 Cd1 O1 C17 -139.3(2) 2_656 . . . ? N4 Cd1 O1 C17 119.30(18) 1_455 . . . ? N1 Cd1 O1 C17 -55.23(18) . . . . ? O4 Cd1 O1 C17 -148.39(17) 2_656 . . . ? C18 Cd1 O1 C17 -145.76(17) 2_656 . . . ? O4 C18 O3 Cd1 -1.3(2) . . . 2_646 ? C13 C18 O3 Cd1 179.89(17) . . . 2_646 ? O3 C18 O4 Cd1 1.2(2) . . . 2_646 ? C13 C18 O4 Cd1 -179.93(18) . . . 2_646 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.715 _refine_diff_density_min -0.702 _refine_diff_density_rms 0.118 _database_code_depnum_ccdc_archive 'CCDC 920973' ####################################################################### # # 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_global # Attachment '4.cif' # Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry data_4 #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H9 Cd N6 O5, 2(O)' _chemical_formula_sum 'C15 H9 Cd N6 O7' _chemical_formula_weight 497.69 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 7.6227(4) _cell_length_b 10.5639(5) _cell_length_c 12.0613(6) _cell_angle_alpha 68.2540(10) _cell_angle_beta 84.7600(10) _cell_angle_gamma 76.6420(10) _cell_volume 877.70(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6818 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.659 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 490 _exptl_absorpt_coefficient_mu 1.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7542 _exptl_absorpt_correction_T_max 0.8596 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker Smart Apex CCD ' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11113 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _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 1.82 _diffrn_reflns_theta_max 27.66 _reflns_number_total 4052 _reflns_number_gt 3766 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0911P)^2^+0.2548P] 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 4052 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.42497(3) 1.02556(2) 0.348385(15) 0.02017(11) Uani 1 1 d . . . C1 C 0.7278(4) 0.5281(3) 0.9732(3) 0.0245(6) Uani 1 1 d . . . C2 C 0.8535(5) 0.4032(3) 0.9955(3) 0.0295(7) Uani 1 1 d . . . H2 H 0.8949 0.3501 1.0726 0.035 Uiso 1 1 calc R . . C3 C 0.9166(5) 0.3583(4) 0.9021(3) 0.0346(8) Uani 1 1 d . . . H3 H 1.0002 0.2745 0.9168 0.041 Uiso 1 1 calc R . . C4 C 0.8558(5) 0.4375(4) 0.7867(3) 0.0323(7) Uani 1 1 d . . . H4 H 0.9003 0.4071 0.7244 0.039 Uiso 1 1 calc R . . C5 C 0.7291(5) 0.5616(3) 0.7639(3) 0.0263(6) Uani 1 1 d . . . C6 C 0.6652(5) 0.6061(3) 0.8574(3) 0.0261(6) Uani 1 1 d . . . H6 H 0.5795 0.6889 0.8428 0.031 Uiso 1 1 calc R . . C7 C 0.6655(5) 0.6453(3) 0.6415(3) 0.0264(6) Uani 1 1 d . . . C8 C 0.6596(5) 0.5818(3) 1.0687(3) 0.0259(6) Uani 1 1 d . . . C9 C 0.5474(5) 0.7038(4) 1.0638(3) 0.0328(7) Uani 1 1 d . . . H9 H 0.4937 0.7740 0.9955 0.039 Uiso 1 1 calc R . . C10 C 0.6236(5) 0.5861(4) 1.2505(3) 0.0348(8) Uani 1 1 d . . . H10 H 0.6316 0.5605 1.3327 0.042 Uiso 1 1 calc R . . C11 C 0.7976(4) 1.0026(3) 0.2168(3) 0.0233(6) Uani 1 1 d . . . C12 C 0.9045(4) 1.0046(3) 0.1040(2) 0.0180(5) Uani 1 1 d . . . C13 C 0.8180(4) 1.0012(3) 0.0083(2) 0.0185(5) Uani 1 1 d . . . H13 H 0.6953 1.0020 0.0139 0.022 Uiso 1 1 calc R . . C14 C 0.9109(4) 0.9967(3) -0.0954(2) 0.0172(5) Uani 1 1 d . . . C15 C 0.8051(4) 0.9876(3) -0.1911(2) 0.0209(6) Uani 1 1 d . . . N1 N 0.6002(4) 0.7824(3) 0.5989(2) 0.0248(5) Uani 1 1 d . . . N2 N 0.5639(4) 0.8120(3) 0.4833(2) 0.0282(6) Uani 1 1 d . . . N3 N 0.6048(6) 0.6989(3) 0.4587(3) 0.0419(8) Uani 1 1 d . . . N4 N 0.6706(6) 0.5914(3) 0.5565(3) 0.0410(8) Uani 1 1 d . . . H4A H 0.7083 0.5056 0.5634 0.049 Uiso 1 1 calc R . . N5 N 0.5273(5) 0.7051(3) 1.1774(3) 0.0378(7) Uani 1 1 d . . . H5 H 0.4634 0.7715 1.1979 0.045 Uiso 1 1 calc R . . N6 N 0.7060(4) 0.5099(3) 1.1879(2) 0.0294(6) Uani 1 1 d . . . O1 O 0.6330(3) 1.0611(3) 0.2033(2) 0.0328(6) Uani 1 1 d . . . O2 O 0.8805(4) 0.9405(4) 0.3125(2) 0.0464(7) Uani 1 1 d . . . O3 O 0.8314(4) 0.8757(2) -0.2095(2) 0.0313(5) Uani 1 1 d . . . O4 O 0.6844(4) 1.0909(3) -0.2444(2) 0.0369(6) Uani 1 1 d . . . O5 O 0.2038(5) 0.9885(4) 0.4961(3) 0.0556(9) Uani 1 1 d . . . O6 O 0.9016(5) 0.2653(3) 0.3252(3) 0.0516(8) Uani 1 1 d . . . O7 O 0.8905(8) 0.3166(5) 0.5280(4) 0.0938(16) 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 0.02054(15) 0.02743(15) 0.01438(14) -0.01048(10) 0.00086(9) -0.00408(10) C1 0.0281(16) 0.0242(14) 0.0216(14) -0.0088(11) -0.0003(12) -0.0054(12) C2 0.0364(18) 0.0252(15) 0.0224(15) -0.0053(12) -0.0072(13) -0.0005(13) C3 0.043(2) 0.0265(15) 0.0312(17) -0.0123(13) -0.0071(15) 0.0046(15) C4 0.044(2) 0.0284(16) 0.0252(16) -0.0141(13) -0.0003(14) -0.0022(15) C5 0.0340(17) 0.0248(14) 0.0210(14) -0.0073(11) -0.0035(12) -0.0085(13) C6 0.0284(16) 0.0232(14) 0.0251(15) -0.0070(12) -0.0023(12) -0.0043(12) C7 0.0343(17) 0.0256(14) 0.0216(14) -0.0108(12) -0.0014(12) -0.0065(13) C8 0.0306(16) 0.0267(14) 0.0208(14) -0.0095(12) -0.0019(12) -0.0049(13) C9 0.0386(19) 0.0269(15) 0.0304(17) -0.0119(13) -0.0027(14) 0.0016(14) C10 0.039(2) 0.0411(19) 0.0252(16) -0.0179(14) -0.0001(14) 0.0000(16) C11 0.0249(15) 0.0321(15) 0.0158(13) -0.0104(11) 0.0044(11) -0.0104(12) C12 0.0167(13) 0.0220(13) 0.0139(12) -0.0069(10) 0.0013(10) -0.0014(11) C13 0.0150(12) 0.0241(13) 0.0167(12) -0.0090(10) 0.0002(10) -0.0022(11) C14 0.0164(13) 0.0201(12) 0.0150(12) -0.0082(10) -0.0014(10) 0.0003(10) C15 0.0183(14) 0.0312(15) 0.0157(13) -0.0114(11) 0.0012(10) -0.0056(12) N1 0.0333(15) 0.0279(13) 0.0153(11) -0.0087(10) -0.0019(10) -0.0082(11) N2 0.0374(15) 0.0316(14) 0.0162(12) -0.0101(10) -0.0040(10) -0.0046(12) N3 0.070(3) 0.0353(16) 0.0231(15) -0.0130(12) -0.0089(15) -0.0091(16) N4 0.069(2) 0.0288(15) 0.0273(15) -0.0160(12) -0.0087(15) -0.0005(15) N5 0.0412(18) 0.0356(16) 0.0385(17) -0.0216(14) 0.0016(14) 0.0013(14) N6 0.0348(16) 0.0308(14) 0.0220(13) -0.0115(11) -0.0019(11) -0.0019(12) O1 0.0230(12) 0.0468(14) 0.0216(12) -0.0112(10) 0.0077(9) 0.0014(11) O2 0.0303(14) 0.084(2) 0.0169(11) -0.0133(12) 0.0013(10) -0.0067(14) O3 0.0418(14) 0.0274(11) 0.0305(12) -0.0177(10) -0.0067(10) -0.0040(10) O4 0.0366(14) 0.0421(14) 0.0353(13) -0.0239(11) -0.0194(11) 0.0097(11) O5 0.062(2) 0.063(2) 0.0478(18) -0.0271(16) 0.0355(17) -0.0261(18) O6 0.0534(19) 0.0387(15) 0.0519(18) -0.0168(13) -0.0092(14) 0.0153(14) O7 0.141(5) 0.079(3) 0.050(2) -0.031(2) -0.016(2) 0.019(3) _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 2.236(2) . ? Cd1 N1 2.304(3) 2_676 ? Cd1 N2 2.313(3) . ? Cd1 O5 2.326(3) . ? Cd1 O4 2.364(2) 2_675 ? Cd1 O3 2.465(2) 2_675 ? Cd1 C15 2.759(3) 2_675 ? Cd1 Cd1 3.7405(4) 2_676 ? C1 C2 1.390(4) . ? C1 C6 1.395(4) . ? C1 C8 1.468(4) . ? C2 C3 1.384(5) . ? C2 H2 0.9300 . ? C3 C4 1.388(5) . ? C3 H3 0.9300 . ? C4 C5 1.387(5) . ? C4 H4 0.9300 . ? C5 C6 1.384(5) . ? C5 C7 1.470(4) . ? C6 H6 0.9300 . ? C7 N1 1.331(4) . ? C7 N4 1.338(4) . ? C8 C9 1.356(5) . ? C8 N6 1.389(4) . ? C9 N5 1.370(5) . ? C9 H9 0.9300 . ? C10 N6 1.320(4) . ? C10 N5 1.329(5) . ? C10 H10 0.9300 . ? C11 O2 1.242(4) . ? C11 O1 1.260(4) . ? C11 C12 1.516(4) . ? C12 C13 1.397(4) . ? C12 C14 1.399(4) 2_775 ? C13 C14 1.390(4) . ? C13 H13 0.9300 . ? C14 C12 1.399(4) 2_775 ? C14 C15 1.510(4) . ? C15 O3 1.250(4) . ? C15 O4 1.255(4) . ? C15 Cd1 2.759(3) 2_675 ? N1 N2 1.352(3) . ? N1 Cd1 2.304(3) 2_676 ? N2 N3 1.298(4) . ? N3 N4 1.336(4) . ? N4 H4A 0.8600 . ? N5 H5 0.8600 . ? O3 Cd1 2.465(2) 2_675 ? O4 Cd1 2.364(2) 2_675 ? 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 101.56(10) . 2_676 ? O1 Cd1 N2 101.07(10) . . ? N1 Cd1 N2 117.07(9) 2_676 . ? O1 Cd1 O5 178.63(10) . . ? N1 Cd1 O5 79.18(11) 2_676 . ? N2 Cd1 O5 79.54(13) . . ? O1 Cd1 O4 84.99(10) . 2_675 ? N1 Cd1 O4 150.21(9) 2_676 2_675 ? N2 Cd1 O4 89.50(9) . 2_675 ? O5 Cd1 O4 93.80(12) . 2_675 ? O1 Cd1 O3 94.20(9) . 2_675 ? N1 Cd1 O3 96.41(8) 2_676 2_675 ? N2 Cd1 O3 138.92(9) . 2_675 ? O5 Cd1 O3 84.56(12) . 2_675 ? O4 Cd1 O3 53.91(8) 2_675 2_675 ? O1 Cd1 C15 88.92(9) . 2_675 ? N1 Cd1 C15 123.35(9) 2_676 2_675 ? N2 Cd1 C15 114.95(9) . 2_675 ? O5 Cd1 C15 89.71(12) . 2_675 ? O4 Cd1 C15 26.97(9) 2_675 2_675 ? O3 Cd1 C15 26.95(8) 2_675 2_675 ? O1 Cd1 Cd1 116.12(7) . 2_676 ? N1 Cd1 Cd1 60.89(6) 2_676 2_676 ? N2 Cd1 Cd1 56.36(7) . 2_676 ? O5 Cd1 Cd1 65.25(11) . 2_676 ? O4 Cd1 Cd1 141.52(7) 2_675 2_676 ? O3 Cd1 Cd1 144.28(6) 2_675 2_676 ? C15 Cd1 Cd1 154.08(6) 2_675 2_676 ? C2 C1 C6 119.7(3) . . ? C2 C1 C8 121.7(3) . . ? C6 C1 C8 118.6(3) . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 119.2(3) . . ? C6 C5 C7 120.6(3) . . ? C4 C5 C7 120.2(3) . . ? C5 C6 C1 120.7(3) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? N1 C7 N4 110.9(3) . . ? N1 C7 C5 125.8(3) . . ? N4 C7 C5 123.3(3) . . ? C9 C8 N6 106.1(3) . . ? C9 C8 C1 130.4(3) . . ? N6 C8 C1 123.5(3) . . ? C8 C9 N5 107.8(3) . . ? C8 C9 H9 126.1 . . ? N5 C9 H9 126.1 . . ? N6 C10 N5 109.2(3) . . ? N6 C10 H10 125.4 . . ? N5 C10 H10 125.4 . . ? O2 C11 O1 127.1(3) . . ? O2 C11 C12 116.6(3) . . ? O1 C11 C12 116.3(3) . . ? C13 C12 C14 119.1(3) . 2_775 ? C13 C12 C11 119.1(3) . . ? C14 C12 C11 121.7(3) 2_775 . ? C14 C13 C12 121.6(3) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C12 119.3(3) . 2_775 ? C13 C14 C15 117.0(3) . . ? C12 C14 C15 123.7(2) 2_775 . ? O3 C15 O4 121.9(3) . . ? O3 C15 C14 119.6(3) . . ? O4 C15 C14 118.3(3) . . ? O3 C15 Cd1 63.29(16) . 2_675 ? O4 C15 Cd1 58.70(16) . 2_675 ? C14 C15 Cd1 173.0(2) . 2_675 ? C7 N1 N2 104.4(2) . . ? C7 N1 Cd1 139.9(2) . 2_676 ? N2 N1 Cd1 114.87(19) . 2_676 ? N3 N2 N1 110.1(3) . . ? N3 N2 Cd1 122.9(2) . . ? N1 N2 Cd1 126.7(2) . . ? N2 N3 N4 109.0(3) . . ? N3 N4 C7 105.6(3) . . ? N3 N4 H4A 127.2 . . ? C7 N4 H4A 127.2 . . ? C10 N5 C9 108.2(3) . . ? C10 N5 H5 125.9 . . ? C9 N5 H5 125.9 . . ? C10 N6 C8 108.6(3) . . ? C11 O1 Cd1 124.7(2) . . ? C15 O3 Cd1 89.76(19) . 2_675 ? C15 O4 Cd1 94.33(19) . 2_675 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.7(5) . . . . ? C8 C1 C2 C3 -178.7(3) . . . . ? C1 C2 C3 C4 0.3(6) . . . . ? C2 C3 C4 C5 -0.9(6) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C3 C4 C5 C7 179.9(3) . . . . ? C4 C5 C6 C1 0.5(5) . . . . ? C7 C5 C6 C1 -178.8(3) . . . . ? C2 C1 C6 C5 -1.2(5) . . . . ? C8 C1 C6 C5 178.3(3) . . . . ? C6 C5 C7 N1 25.2(5) . . . . ? C4 C5 C7 N1 -154.2(3) . . . . ? C6 C5 C7 N4 -156.5(4) . . . . ? C4 C5 C7 N4 24.1(5) . . . . ? C2 C1 C8 C9 175.3(4) . . . . ? C6 C1 C8 C9 -4.1(6) . . . . ? C2 C1 C8 N6 -3.8(5) . . . . ? C6 C1 C8 N6 176.8(3) . . . . ? N6 C8 C9 N5 0.1(4) . . . . ? C1 C8 C9 N5 -179.1(4) . . . . ? O2 C11 C12 C13 146.1(3) . . . . ? O1 C11 C12 C13 -32.1(4) . . . . ? O2 C11 C12 C14 -30.9(4) . . . 2_775 ? O1 C11 C12 C14 150.9(3) . . . 2_775 ? C14 C12 C13 C14 0.0(5) 2_775 . . . ? C11 C12 C13 C14 -177.2(3) . . . . ? C12 C13 C14 C12 0.0(5) . . . 2_775 ? C12 C13 C14 C15 177.7(3) . . . . ? C13 C14 C15 O3 -107.5(3) . . . . ? C12 C14 C15 O3 70.0(4) 2_775 . . . ? C13 C14 C15 O4 67.9(4) . . . . ? C12 C14 C15 O4 -114.6(3) 2_775 . . . ? N4 C7 N1 N2 0.2(4) . . . . ? C5 C7 N1 N2 178.7(3) . . . . ? N4 C7 N1 Cd1 -167.5(3) . . . 2_676 ? C5 C7 N1 Cd1 10.9(6) . . . 2_676 ? C7 N1 N2 N3 0.2(4) . . . . ? Cd1 N1 N2 N3 171.5(3) 2_676 . . . ? C7 N1 N2 Cd1 174.8(2) . . . . ? Cd1 N1 N2 Cd1 -13.9(3) 2_676 . . . ? O1 Cd1 N2 N3 -62.7(3) . . . . ? N1 Cd1 N2 N3 -171.9(3) 2_676 . . . ? O5 Cd1 N2 N3 116.1(3) . . . . ? O4 Cd1 N2 N3 22.1(3) 2_675 . . . ? O3 Cd1 N2 N3 47.1(4) 2_675 . . . ? C15 Cd1 N2 N3 31.4(3) 2_675 . . . ? Cd1 Cd1 N2 N3 -176.8(3) 2_676 . . . ? O1 Cd1 N2 N1 123.4(3) . . . . ? N1 Cd1 N2 N1 14.2(3) 2_676 . . . ? O5 Cd1 N2 N1 -57.9(3) . . . . ? O4 Cd1 N2 N1 -151.8(3) 2_675 . . . ? O3 Cd1 N2 N1 -126.9(2) 2_675 . . . ? C15 Cd1 N2 N1 -142.6(3) 2_675 . . . ? Cd1 Cd1 N2 N1 9.3(2) 2_676 . . . ? N1 N2 N3 N4 -0.5(5) . . . . ? Cd1 N2 N3 N4 -175.4(3) . . . . ? N2 N3 N4 C7 0.6(5) . . . . ? N1 C7 N4 N3 -0.5(5) . . . . ? C5 C7 N4 N3 -179.0(4) . . . . ? N6 C10 N5 C9 0.8(5) . . . . ? C8 C9 N5 C10 -0.6(5) . . . . ? N5 C10 N6 C8 -0.7(4) . . . . ? C9 C8 N6 C10 0.4(4) . . . . ? C1 C8 N6 C10 179.6(3) . . . . ? O2 C11 O1 Cd1 -16.2(5) . . . . ? C12 C11 O1 Cd1 161.8(2) . . . . ? N1 Cd1 O1 C11 99.8(3) 2_676 . . . ? N2 Cd1 O1 C11 -21.1(3) . . . . ? O4 Cd1 O1 C11 -109.6(3) 2_675 . . . ? O3 Cd1 O1 C11 -162.8(3) 2_675 . . . ? C15 Cd1 O1 C11 -136.3(3) 2_675 . . . ? Cd1 Cd1 O1 C11 36.7(3) 2_676 . . . ? O4 C15 O3 Cd1 -2.5(3) . . . 2_675 ? C14 C15 O3 Cd1 172.7(2) . . . 2_675 ? O3 C15 O4 Cd1 2.6(3) . . . 2_675 ? C14 C15 O4 Cd1 -172.7(2) . . . 2_675 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.66 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.985 _refine_diff_density_min -0.825 _refine_diff_density_rms 0.258 _database_code_depnum_ccdc_archive 'CCDC 920974' ####################################################################### # # 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_global # Attachment '5.cif' # Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry data_5 #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H9 N6 O4 Zn' _chemical_formula_sum 'C15 H9 N6 O4 Zn' _chemical_formula_weight 402.65 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 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.9451(11) _cell_length_b 8.3941(5) _cell_length_c 19.5874(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2950.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3943 _cell_measurement_theta_min 2.874 _cell_measurement_theta_max 27.522 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.813 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 1.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7161 _exptl_absorpt_correction_T_max 0.8481 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker Smart Apex CCD ' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10276 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3369 _reflns_number_gt 2830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0969P)^2^+0.2898P] 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 3369 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.211684(18) 0.74047(4) 0.491121(17) 0.01944(15) Uani 1 1 d . . . C1 C 0.33548(14) 0.6112(3) 0.22194(12) 0.0237(5) Uani 1 1 d . . . C2 C 0.39159(16) 0.7001(4) 0.25412(14) 0.0264(6) Uani 1 1 d . . . H2 H 0.4398 0.6985 0.2368 0.032 Uiso 1 1 calc R . . C3 C 0.37572(16) 0.7896(3) 0.31121(14) 0.0269(6) Uani 1 1 d . . . H3 H 0.4133 0.8489 0.3318 0.032 Uiso 1 1 calc R . . C4 C 0.30464(16) 0.7925(3) 0.33838(14) 0.0247(5) Uani 1 1 d . . . H4 H 0.2944 0.8530 0.3771 0.030 Uiso 1 1 calc R . . C5 C 0.24823(15) 0.7036(3) 0.30711(13) 0.0212(5) Uani 1 1 d . . . C6 C 0.26383(15) 0.6141(3) 0.24933(12) 0.0234(6) Uani 1 1 d . . . H6 H 0.2261 0.5554 0.2287 0.028 Uiso 1 1 calc R . . C7 C 0.34941(14) 0.5187(3) 0.16001(13) 0.0240(5) Uani 1 1 d . . . C8 C 0.30538(14) 0.4148(3) 0.12531(13) 0.0253(6) Uani 1 1 d . . . H8 H 0.2581 0.3822 0.1388 0.030 Uiso 1 1 calc R . . C9 C 0.40688(15) 0.4376(4) 0.06715(14) 0.0291(6) Uani 1 1 d . . . H9 H 0.4430 0.4258 0.0335 0.035 Uiso 1 1 calc R . . C10 C 0.17301(14) 0.7001(3) 0.33595(13) 0.0204(5) Uani 1 1 d . . . C11 C 0.03493(13) 1.0671(3) 0.44419(12) 0.0208(5) Uani 1 1 d . . . H11 H 0.0580 1.1131 0.4065 0.025 Uiso 1 1 calc R . . C12 C 0.07593(14) 1.0435(3) 0.50367(12) 0.0184(5) Uani 1 1 d . . . C13 C 0.04012(13) 0.9767(3) 0.56027(12) 0.0190(5) Uani 1 1 d . . . C14 C 0.08136(13) 0.9589(3) 0.62621(12) 0.0227(5) Uani 1 1 d . . . C15 C 0.15780(14) 1.0848(3) 0.50168(11) 0.0178(5) Uani 1 1 d . . . N1 N 0.15796(12) 0.7027(3) 0.40284(11) 0.0224(5) Uani 1 1 d . . . N2 N 0.08305(12) 0.6885(3) 0.40858(11) 0.0275(5) Uani 1 1 d . . . N3 N 0.05510(13) 0.6793(3) 0.34764(12) 0.0288(5) Uani 1 1 d . . . N4 N 0.11015(12) 0.6851(3) 0.30038(11) 0.0263(5) Uani 1 1 d . . . H4A H 0.1055 0.6802 0.2567 0.032 Uiso 1 1 calc R . . N5 N 0.34163(12) 0.3650(3) 0.06686(11) 0.0240(5) Uani 1 1 d . . . N6 N 0.41417(12) 0.5297(3) 0.12197(11) 0.0291(5) Uani 1 1 d . . . H6A H 0.4525 0.5864 0.1320 0.035 Uiso 1 1 calc R . . O1 O 0.20573(10) 0.9768(3) 0.49439(10) 0.0271(5) Uani 1 1 d . . . O2 O 0.17674(13) 1.2288(2) 0.50101(11) 0.0255(5) Uani 1 1 d . . . O3 O 0.13779(11) 1.0309(3) 0.63757(11) 0.0400(6) Uani 1 1 d . . . O4 O 0.05012(11) 0.8581(3) 0.66982(9) 0.0352(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 0.0140(2) 0.0262(2) 0.0182(2) -0.00029(10) -0.00107(10) 0.00029(10) C1 0.0194(13) 0.0329(14) 0.0189(11) -0.0002(10) -0.0003(10) -0.0022(11) C2 0.0153(13) 0.0377(15) 0.0262(13) 0.0011(11) -0.0003(10) -0.0040(13) C3 0.0230(14) 0.0321(13) 0.0257(14) 0.0007(11) -0.0050(11) -0.0074(11) C4 0.0270(14) 0.0278(12) 0.0193(13) -0.0029(10) -0.0021(11) -0.0027(12) C5 0.0181(12) 0.0274(12) 0.0182(11) 0.0013(10) 0.0005(10) -0.0012(10) C6 0.0189(14) 0.0321(14) 0.0192(11) -0.0017(10) -0.0019(9) -0.0037(11) C7 0.0160(12) 0.0349(14) 0.0212(12) -0.0006(10) 0.0018(9) -0.0002(11) C8 0.0154(11) 0.0380(15) 0.0225(12) -0.0037(11) 0.0015(10) -0.0012(11) C9 0.0197(13) 0.0431(16) 0.0246(13) -0.0057(11) 0.0034(10) -0.0008(12) C10 0.0181(12) 0.0246(12) 0.0186(12) -0.0034(9) -0.0009(9) -0.0005(10) C11 0.0163(12) 0.0286(13) 0.0176(11) 0.0039(9) 0.0000(9) -0.0033(10) C12 0.0129(11) 0.0217(12) 0.0205(11) 0.0006(9) 0.0000(9) -0.0006(9) C13 0.0138(11) 0.0260(12) 0.0171(11) 0.0012(9) -0.0018(9) 0.0000(9) C14 0.0149(11) 0.0369(14) 0.0164(11) 0.0002(10) 0.0001(9) 0.0007(11) C15 0.0143(11) 0.0245(12) 0.0147(10) 0.0013(9) -0.0006(8) -0.0015(10) N1 0.0160(10) 0.0320(11) 0.0192(10) -0.0027(9) -0.0004(8) 0.0005(9) N2 0.0178(11) 0.0421(13) 0.0225(11) -0.0040(10) -0.0002(9) -0.0021(10) N3 0.0186(11) 0.0424(14) 0.0255(11) -0.0043(10) -0.0014(9) -0.0011(10) N4 0.0195(11) 0.0419(13) 0.0175(10) -0.0042(9) -0.0025(8) -0.0032(10) N5 0.0173(10) 0.0348(12) 0.0199(10) -0.0014(9) 0.0002(8) 0.0005(9) N6 0.0190(11) 0.0433(14) 0.0249(11) -0.0077(10) 0.0037(9) -0.0076(10) O1 0.0175(9) 0.0252(11) 0.0386(12) -0.0040(8) -0.0009(7) 0.0023(8) O2 0.0155(11) 0.0236(10) 0.0374(11) 0.0010(7) 0.0009(8) -0.0032(8) O3 0.0269(11) 0.0643(15) 0.0288(11) 0.0086(10) -0.0100(8) -0.0173(11) O4 0.0245(10) 0.0591(14) 0.0220(9) 0.0140(9) -0.0031(8) -0.0092(10) _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 N5 1.975(2) 2_565 ? Zn1 O1 1.988(2) . ? Zn1 N1 2.005(2) . ? Zn1 O2 2.014(2) 8_655 ? C1 C6 1.393(4) . ? C1 C2 1.402(4) . ? C1 C7 1.462(3) . ? C2 C3 1.377(4) . ? C2 H2 0.9300 . ? C3 C4 1.382(4) . ? C3 H3 0.9300 . ? C4 C5 1.399(4) . ? C4 H4 0.9300 . ? C5 C6 1.387(4) . ? C5 C10 1.464(4) . ? C6 H6 0.9300 . ? C7 C8 1.359(4) . ? C7 N6 1.383(3) . ? C8 N5 1.381(3) . ? C8 H8 0.9300 . ? C9 N5 1.320(3) . ? C9 N6 1.330(3) . ? C9 H9 0.9300 . ? C10 N4 1.332(3) . ? C10 N1 1.338(3) . ? C11 C12 1.392(3) . ? C11 C13 1.399(3) 5_576 ? C11 H11 0.9300 . ? C12 C13 1.399(3) . ? C12 C15 1.510(3) . ? C13 C11 1.399(3) 5_576 ? C13 C14 1.496(3) . ? C14 O3 1.200(3) . ? C14 O4 1.327(3) . ? C15 O2 1.256(3) . ? C15 O1 1.257(3) . ? N1 N2 1.354(3) . ? N2 N3 1.297(3) . ? N3 N4 1.355(3) . ? N4 H4A 0.8600 . ? N5 Zn1 1.975(2) 2_564 ? N6 H6A 0.8600 . ? O2 Zn1 2.014(2) 8_665 ? 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 N5 Zn1 O1 113.40(9) 2_565 . ? N5 Zn1 N1 110.13(9) 2_565 . ? O1 Zn1 N1 99.19(9) . . ? N5 Zn1 O2 112.81(9) 2_565 8_655 ? O1 Zn1 O2 95.67(8) . 8_655 ? N1 Zn1 O2 123.59(9) . 8_655 ? C6 C1 C2 118.7(2) . . ? C6 C1 C7 119.1(2) . . ? C2 C1 C7 122.2(2) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 119.3(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.0(2) . . ? C6 C5 C10 119.4(2) . . ? C4 C5 C10 120.6(2) . . ? C5 C6 C1 120.7(2) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C8 C7 N6 105.2(2) . . ? C8 C7 C1 131.0(2) . . ? N6 C7 C1 123.7(2) . . ? C7 C8 N5 109.6(2) . . ? C7 C8 H8 125.2 . . ? N5 C8 H8 125.2 . . ? N5 C9 N6 111.0(2) . . ? N5 C9 H9 124.5 . . ? N6 C9 H9 124.5 . . ? N4 C10 N1 110.1(2) . . ? N4 C10 C5 125.5(2) . . ? N1 C10 C5 124.3(2) . . ? C12 C11 C13 121.6(2) . 5_576 ? C12 C11 H11 119.2 . . ? C13 C11 H11 119.2 5_576 . ? C11 C12 C13 118.5(2) . . ? C11 C12 C15 117.4(2) . . ? C13 C12 C15 124.0(2) . . ? C12 C13 C11 119.9(2) . 5_576 ? C12 C13 C14 119.8(2) . . ? C11 C13 C14 120.3(2) 5_576 . ? O3 C14 O4 123.9(2) . . ? O3 C14 C13 121.8(2) . . ? O4 C14 C13 114.2(2) . . ? O2 C15 O1 120.5(2) . . ? O2 C15 C12 119.0(2) . . ? O1 C15 C12 120.2(2) . . ? C10 N1 N2 106.3(2) . . ? C10 N1 Zn1 138.60(18) . . ? N2 N1 Zn1 114.81(16) . . ? N3 N2 N1 108.2(2) . . ? N2 N3 N4 110.2(2) . . ? C10 N4 N3 105.3(2) . . ? C10 N4 H4A 127.4 . . ? N3 N4 H4A 127.4 . . ? C9 N5 C8 105.9(2) . . ? C9 N5 Zn1 129.78(18) . 2_564 ? C8 N5 Zn1 122.02(17) . 2_564 ? C9 N6 C7 108.3(2) . . ? C9 N6 H6A 125.9 . . ? C7 N6 H6A 125.9 . . ? C15 O1 Zn1 139.42(18) . . ? C15 O2 Zn1 108.46(18) . 8_665 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.7(4) . . . . ? C7 C1 C2 C3 178.0(3) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C3 C4 C5 C10 178.0(2) . . . . ? C4 C5 C6 C1 0.2(4) . . . . ? C10 C5 C6 C1 -178.0(2) . . . . ? C2 C1 C6 C5 0.3(4) . . . . ? C7 C1 C6 C5 -178.5(3) . . . . ? C6 C1 C7 C8 -8.3(5) . . . . ? C2 C1 C7 C8 173.0(3) . . . . ? C6 C1 C7 N6 168.2(3) . . . . ? C2 C1 C7 N6 -10.6(4) . . . . ? N6 C7 C8 N5 -0.9(3) . . . . ? C1 C7 C8 N5 176.0(3) . . . . ? C6 C5 C10 N4 -33.5(4) . . . . ? C4 C5 C10 N4 148.4(3) . . . . ? C6 C5 C10 N1 142.7(3) . . . . ? C4 C5 C10 N1 -35.5(4) . . . . ? C13 C11 C12 C13 -1.1(4) 5_576 . . . ? C13 C11 C12 C15 176.0(2) 5_576 . . . ? C11 C12 C13 C11 1.1(4) . . . 5_576 ? C15 C12 C13 C11 -175.8(2) . . . 5_576 ? C11 C12 C13 C14 -176.3(2) . . . . ? C15 C12 C13 C14 6.8(4) . . . . ? C12 C13 C14 O3 17.1(4) . . . . ? C11 C13 C14 O3 -160.2(3) 5_576 . . . ? C12 C13 C14 O4 -162.9(2) . . . . ? C11 C13 C14 O4 19.8(3) 5_576 . . . ? C11 C12 C15 O2 73.1(3) . . . . ? C13 C12 C15 O2 -110.0(3) . . . . ? C11 C12 C15 O1 -100.3(3) . . . . ? C13 C12 C15 O1 76.6(3) . . . . ? N4 C10 N1 N2 0.1(3) . . . . ? C5 C10 N1 N2 -176.5(2) . . . . ? N4 C10 N1 Zn1 -172.7(2) . . . . ? C5 C10 N1 Zn1 10.7(4) . . . . ? N5 Zn1 N1 C10 -156.2(3) 2_565 . . . ? O1 Zn1 N1 C10 84.6(3) . . . . ? O2 Zn1 N1 C10 -18.5(3) 8_655 . . . ? N5 Zn1 N1 N2 31.5(2) 2_565 . . . ? O1 Zn1 N1 N2 -87.74(19) . . . . ? O2 Zn1 N1 N2 169.11(16) 8_655 . . . ? C10 N1 N2 N3 -0.5(3) . . . . ? Zn1 N1 N2 N3 174.25(18) . . . . ? N1 N2 N3 N4 0.7(3) . . . . ? N1 C10 N4 N3 0.3(3) . . . . ? C5 C10 N4 N3 176.9(2) . . . . ? N2 N3 N4 C10 -0.6(3) . . . . ? N6 C9 N5 C8 0.0(3) . . . . ? N6 C9 N5 Zn1 162.8(2) . . . 2_564 ? C7 C8 N5 C9 0.6(3) . . . . ? C7 C8 N5 Zn1 -163.86(19) . . . 2_564 ? N5 C9 N6 C7 -0.6(3) . . . . ? C8 C7 N6 C9 0.9(3) . . . . ? C1 C7 N6 C9 -176.3(3) . . . . ? O2 C15 O1 Zn1 179.77(19) . . . . ? C12 C15 O1 Zn1 -6.9(4) . . . . ? N5 Zn1 O1 C15 -48.5(3) 2_565 . . . ? N1 Zn1 O1 C15 68.2(3) . . . . ? O2 Zn1 O1 C15 -166.4(3) 8_655 . . . ? O1 C15 O2 Zn1 -2.3(3) . . . 8_665 ? C12 C15 O2 Zn1 -175.74(16) . . . 8_665 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.359 _refine_diff_density_min -1.377 _refine_diff_density_rms 0.407 _database_code_depnum_ccdc_archive 'CCDC 920975' ####################################################################### # # 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_global # Attachment '6.cif' # Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry data_6 #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C45 H27 N18 O12 Zn3' _chemical_formula_sum 'C45 H27 N18 O12 Zn3' _chemical_formula_weight 1208.02 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 'P 21/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 12.8475(10) _cell_length_b 19.5073(15) _cell_length_c 17.9838(13) _cell_angle_alpha 90.00 _cell_angle_beta 95.3120(10) _cell_angle_gamma 90.00 _cell_volume 4487.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5747 _cell_measurement_theta_min 2.274 _cell_measurement_theta_max 27.529 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2435 _exptl_absorpt_coefficient_mu 1.681 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6885 _exptl_absorpt_correction_T_max 0.7191 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker Smart Apex CCD ' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30159 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.57 _reflns_number_total 10320 _reflns_number_gt 7093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0778P)^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 10320 _refine_ls_number_parameters 703 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.49655(3) 0.51086(2) 0.245271(19) 0.02045(11) Uani 1 1 d . . . Zn2 Zn 0.82539(3) 0.49014(2) -0.30343(2) 0.02037(11) Uani 1 1 d . . . Zn3 Zn 0.84687(3) 0.50887(2) 0.20194(2) 0.01967(11) Uani 1 1 d . . . C1 C 0.4655(3) 0.66666(19) 0.15811(19) 0.0282(8) Uani 1 1 d . . . H1 H 0.4219 0.6299 0.1660 0.034 Uiso 1 1 calc R . . C2 C 0.4670(3) 0.6949(2) 0.0879(2) 0.0355(9) Uani 1 1 d . . . H2 H 0.4249 0.6761 0.0483 0.043 Uiso 1 1 calc R . . C3 C 0.5291(3) 0.75003(19) 0.0750(2) 0.0305(8) Uani 1 1 d . . . H3 H 0.5284 0.7684 0.0272 0.037 Uiso 1 1 calc R . . C4 C 0.5936(3) 0.77864(18) 0.13410(18) 0.0227(7) Uani 1 1 d . . . C5 C 0.5935(3) 0.74990(17) 0.20504(18) 0.0232(7) Uani 1 1 d . . . H5 H 0.6361 0.7683 0.2447 0.028 Uiso 1 1 calc R . . C6 C 0.5305(3) 0.69419(17) 0.21699(17) 0.0219(7) Uani 1 1 d . . . C7 C 0.5309(3) 0.66408(17) 0.29223(17) 0.0216(7) Uani 1 1 d . . . C8 C 0.6569(3) 0.83928(18) 0.12371(17) 0.0241(7) Uani 1 1 d . . . C9 C 0.7248(3) 0.87461(18) 0.17191(18) 0.0264(8) Uani 1 1 d . . . H9 H 0.7463 0.8612 0.2205 0.032 Uiso 1 1 calc R . . C10 C 0.7116(3) 0.9322(2) 0.06949(19) 0.0308(8) Uani 1 1 d . . . H10 H 0.7204 0.9655 0.0336 0.037 Uiso 1 1 calc R . . C11 C 0.7935(3) 0.25321(19) 0.3715(2) 0.0279(8) Uani 1 1 d . . . H11 H 0.7958 0.2726 0.4188 0.034 Uiso 1 1 calc R . . C12 C 0.8531(3) 0.1962(2) 0.35971(19) 0.0287(8) Uani 1 1 d . . . H12 H 0.8948 0.1773 0.3995 0.034 Uiso 1 1 calc R . . C13 C 0.8521(3) 0.16648(19) 0.28974(19) 0.0261(8) Uani 1 1 d . . . H13 H 0.8934 0.1284 0.2823 0.031 Uiso 1 1 calc R . . C14 C 0.7881(3) 0.19467(18) 0.23054(18) 0.0234(7) Uani 1 1 d . . . C15 C 0.7281(3) 0.25176(18) 0.24204(19) 0.0265(8) Uani 1 1 d . . . H15 H 0.6859 0.2704 0.2023 0.032 Uiso 1 1 calc R . . C16 C 0.7298(3) 0.28195(18) 0.31278(18) 0.0242(7) Uani 1 1 d . . . C17 C 0.7827(3) 0.16453(18) 0.15555(18) 0.0236(7) Uani 1 1 d . . . C18 C 0.6647(3) 0.34267(18) 0.32166(18) 0.0253(7) Uani 1 1 d . . . C19 C 0.5992(3) 0.37720(18) 0.27193(18) 0.0271(8) Uani 1 1 d . . . H19 H 0.5839 0.3647 0.2222 0.032 Uiso 1 1 calc R . . C20 C 0.5992(3) 0.4314(2) 0.37583(19) 0.0329(9) Uani 1 1 d . . . H20 H 0.5856 0.4634 0.4120 0.039 Uiso 1 1 calc R . . C21 C 1.1372(3) 0.24610(19) 0.1178(2) 0.0297(8) Uani 1 1 d . . . H21 H 1.1384 0.2639 0.0700 0.036 Uiso 1 1 calc R . . C22 C 1.1949(3) 0.18880(19) 0.13776(19) 0.0281(8) Uani 1 1 d . . . H22 H 1.2345 0.1682 0.1032 0.034 Uiso 1 1 calc R . . C23 C 1.1949(3) 0.16123(18) 0.20893(18) 0.0243(7) Uani 1 1 d . . . H23 H 1.2341 0.1223 0.2223 0.029 Uiso 1 1 calc R . . C24 C 1.1354(3) 0.19263(18) 0.25997(18) 0.0235(7) Uani 1 1 d . . . C25 C 1.0774(3) 0.25073(18) 0.23999(18) 0.0255(8) Uani 1 1 d . . . H25 H 1.0385 0.2717 0.2747 0.031 Uiso 1 1 calc R . . C26 C 1.0768(3) 0.27806(18) 0.16832(18) 0.0235(7) Uani 1 1 d . . . C27 C 1.1290(3) 0.16392(18) 0.33502(17) 0.0220(7) Uani 1 1 d . . . C28 C 1.0158(3) 0.34007(18) 0.15051(18) 0.0245(7) Uani 1 1 d . . . C29 C 0.9485(3) 0.37454(19) 0.19046(18) 0.0279(8) Uani 1 1 d . . . H29 H 0.9275 0.3606 0.2362 0.033 Uiso 1 1 calc R . . C30 C 0.9630(3) 0.43335(19) 0.09063(18) 0.0284(8) Uani 1 1 d . . . H30 H 0.9555 0.4674 0.0543 0.034 Uiso 1 1 calc R . . C31 C 0.7255(2) 0.44804(17) -0.05339(17) 0.0201(7) Uani 1 1 d . . . H31 H 0.7561 0.4102 -0.0742 0.024 Uiso 1 1 calc R . . C32 C 0.7074(2) 0.50673(16) -0.09613(17) 0.0177(6) Uani 1 1 d . . . C33 C 0.6639(2) 0.56359(17) -0.06357(17) 0.0201(7) Uani 1 1 d . . . C34 C 0.6394(2) 0.56059(17) 0.01033(17) 0.0203(7) Uani 1 1 d . . . H34 H 0.6119 0.5991 0.0319 0.024 Uiso 1 1 calc R . . C35 C 0.6551(2) 0.50132(16) 0.05199(16) 0.0174(6) Uani 1 1 d . . . C36 C 0.6993(2) 0.44415(17) 0.02008(17) 0.0197(7) Uani 1 1 d . . . C37 C 0.7057(3) 0.37743(18) 0.06095(17) 0.0240(7) Uani 1 1 d . . . C38 C 0.6250(2) 0.50300(16) 0.13142(17) 0.0174(6) Uani 1 1 d . . . C39 C 0.6416(3) 0.62683(19) -0.10859(18) 0.0270(8) Uani 1 1 d . . . C40 C 0.7297(2) 0.50217(16) -0.17752(17) 0.0189(7) Uani 1 1 d . . . C41 C 1.0415(2) 0.44346(17) -0.46218(17) 0.0202(7) Uani 1 1 d . . . H41 H 1.0692 0.4052 -0.4367 0.024 Uiso 1 1 calc R . . C42 C 1.0263(2) 0.50336(16) -0.42266(17) 0.0175(6) Uani 1 1 d . . . C43 C 0.9840(2) 0.56058(17) -0.46089(17) 0.0197(7) Uani 1 1 d . . . C44 C 0.9716(3) 0.62570(18) -0.42012(18) 0.0253(7) Uani 1 1 d . . . C45 C 1.0523(3) 0.50006(16) -0.33872(17) 0.0196(7) Uani 1 1 d . . . N1 N 0.5471(2) 0.69794(15) 0.35631(15) 0.0283(7) Uani 1 1 d . . . H1A H 0.5574 0.7412 0.3621 0.034 Uiso 1 1 calc R . . N2 N 0.5438(3) 0.65041(16) 0.41040(15) 0.0316(7) Uani 1 1 d . . . N3 N 0.5268(3) 0.58975(16) 0.38083(15) 0.0313(7) Uani 1 1 d . . . N4 N 0.5189(2) 0.59698(15) 0.30548(15) 0.0247(6) Uani 1 1 d . . . N5 N 0.7571(2) 0.93307(15) 0.13817(15) 0.0241(6) Uani 1 1 d . . . N6 N 0.6511(2) 0.87688(15) 0.05845(15) 0.0285(7) Uani 1 1 d . . . H6 H 0.6145 0.8664 0.0175 0.034 Uiso 1 1 calc R . . N7 N 0.7917(2) 0.09753(15) 0.14146(14) 0.0251(6) Uani 1 1 d . . . N8 N 0.7780(3) 0.09055(16) 0.06591(16) 0.0331(7) Uani 1 1 d . . . N9 N 0.7616(3) 0.15099(17) 0.03701(17) 0.0376(8) Uani 1 1 d . . . N10 N 0.7641(3) 0.19835(16) 0.09186(16) 0.0348(8) Uani 1 1 d . . . H10A H 0.7554 0.2418 0.0865 0.042 Uiso 1 1 calc R . . N11 N 0.6617(3) 0.37795(16) 0.38792(16) 0.0337(7) Uani 1 1 d . . . H11A H 0.6949 0.3670 0.4300 0.040 Uiso 1 1 calc R . . N12 N 0.5583(2) 0.43350(15) 0.30507(15) 0.0258(6) Uani 1 1 d . . . N13 N 1.1182(2) 0.19955(15) 0.39649(15) 0.0282(7) Uani 1 1 d . . . H13A H 1.1166 0.2434 0.4007 0.034 Uiso 1 1 calc R . . N14 N 1.1104(2) 0.15309(16) 0.45103(15) 0.0289(7) Uani 1 1 d . . . N15 N 1.1150(2) 0.09162(15) 0.42389(15) 0.0279(7) Uani 1 1 d . . . N16 N 1.1272(2) 0.09704(15) 0.35007(14) 0.0233(6) Uani 1 1 d . . . N17 N 1.0225(2) 0.37795(15) 0.08672(15) 0.0286(7) Uani 1 1 d . . . H17 H 1.0589 0.3676 0.0505 0.034 Uiso 1 1 calc R . . N18 N 0.9159(2) 0.43370(15) 0.15284(15) 0.0242(6) Uani 1 1 d . . . O1 O 0.69295(18) 0.50643(13) 0.18614(13) 0.0281(6) Uani 1 1 d . . . O2 O 0.52929(18) 0.50592(13) 0.13994(13) 0.0281(6) Uani 1 1 d . . . O3 O 0.6541(3) 0.36650(15) 0.11233(15) 0.0500(8) Uani 1 1 d . . . O4 O 0.7688(2) 0.33142(13) 0.03513(13) 0.0313(6) Uani 1 1 d . . . O5 O 0.82205(18) 0.50645(13) -0.19303(13) 0.0288(6) Uani 1 1 d . . . O6 O 0.65798(18) 0.48708(14) -0.22702(13) 0.0297(6) Uani 1 1 d . . . O7 O 0.6611(4) 0.63102(18) -0.17176(17) 0.0907(16) Uani 1 1 d . . . O8 O 0.5987(3) 0.67705(15) -0.07492(14) 0.0490(8) Uani 1 1 d . . . O9 O 1.14596(18) 0.50163(13) -0.31310(12) 0.0254(5) Uani 1 1 d . . . O10 O 0.98009(18) 0.49096(13) -0.29675(13) 0.0279(6) Uani 1 1 d . . . O11 O 1.0143(2) 0.63589(14) -0.35879(14) 0.0446(8) Uani 1 1 d . . . O12 O 0.9092(2) 0.67109(13) -0.45643(13) 0.0384(7) 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 0.0265(2) 0.0202(2) 0.01462(19) -0.00116(15) 0.00163(15) 0.00024(16) Zn2 0.0275(2) 0.0188(2) 0.01477(19) -0.00128(14) 0.00183(15) 0.00023(15) Zn3 0.0261(2) 0.0189(2) 0.01392(19) 0.00092(14) 0.00169(14) -0.00008(15) C1 0.0365(19) 0.0208(19) 0.0267(18) 0.0020(14) -0.0011(15) -0.0082(15) C2 0.049(2) 0.031(2) 0.0236(19) -0.0020(16) -0.0099(16) -0.0118(18) C3 0.046(2) 0.027(2) 0.0168(17) 0.0011(14) -0.0018(15) -0.0045(16) C4 0.0305(17) 0.0179(18) 0.0195(16) -0.0021(13) 0.0017(13) 0.0023(14) C5 0.0309(18) 0.0212(19) 0.0169(16) -0.0019(13) -0.0012(13) -0.0031(14) C6 0.0303(17) 0.0198(18) 0.0155(15) 0.0000(13) 0.0022(13) 0.0008(14) C7 0.0294(17) 0.0175(18) 0.0175(16) -0.0002(13) 0.0002(13) -0.0009(14) C8 0.0335(18) 0.0236(19) 0.0155(16) 0.0003(13) 0.0026(13) -0.0005(15) C9 0.0379(19) 0.025(2) 0.0160(16) 0.0013(14) 0.0007(14) -0.0057(15) C10 0.045(2) 0.028(2) 0.0181(17) 0.0023(14) 0.0010(15) -0.0064(17) C11 0.035(2) 0.030(2) 0.0178(17) -0.0017(14) -0.0005(14) -0.0015(16) C12 0.0323(19) 0.030(2) 0.0222(18) 0.0034(15) -0.0042(14) 0.0000(16) C13 0.0286(17) 0.023(2) 0.0258(18) 0.0016(14) -0.0013(14) 0.0033(14) C14 0.0326(18) 0.0198(18) 0.0178(16) 0.0012(13) 0.0022(13) -0.0003(14) C15 0.039(2) 0.021(2) 0.0181(17) 0.0027(13) -0.0009(15) 0.0021(15) C16 0.0330(18) 0.0215(19) 0.0180(16) 0.0011(13) 0.0025(13) -0.0012(14) C17 0.0336(18) 0.0182(18) 0.0186(16) 0.0023(13) 0.0010(13) 0.0004(14) C18 0.0371(19) 0.0198(19) 0.0189(16) 0.0001(14) 0.0020(14) 0.0019(15) C19 0.040(2) 0.025(2) 0.0170(16) -0.0017(14) 0.0045(14) 0.0033(16) C20 0.050(2) 0.028(2) 0.0199(18) -0.0034(15) 0.0021(16) 0.0106(18) C21 0.043(2) 0.028(2) 0.0195(18) 0.0012(14) 0.0087(15) 0.0019(16) C22 0.0334(18) 0.029(2) 0.0232(18) -0.0047(15) 0.0096(14) 0.0031(16) C23 0.0276(17) 0.0194(19) 0.0265(18) 0.0001(14) 0.0056(14) 0.0019(14) C24 0.0347(18) 0.0181(18) 0.0175(16) 0.0002(13) 0.0010(13) 0.0000(14) C25 0.0351(19) 0.0218(19) 0.0203(18) -0.0023(14) 0.0071(14) 0.0039(14) C26 0.0331(18) 0.0167(18) 0.0212(17) -0.0017(13) 0.0060(14) 0.0008(14) C27 0.0267(16) 0.0210(19) 0.0190(16) -0.0009(13) 0.0049(13) 0.0027(14) C28 0.0343(18) 0.0230(19) 0.0164(16) 0.0029(13) 0.0036(13) 0.0002(15) C29 0.043(2) 0.024(2) 0.0164(16) 0.0045(14) 0.0018(14) 0.0016(16) C30 0.041(2) 0.025(2) 0.0196(17) 0.0054(14) 0.0060(14) 0.0045(16) C31 0.0250(16) 0.0189(18) 0.0164(15) -0.0022(12) 0.0011(12) 0.0024(13) C32 0.0204(14) 0.0193(18) 0.0133(15) -0.0007(12) 0.0014(11) -0.0014(12) C33 0.0243(16) 0.0206(18) 0.0152(15) 0.0037(12) 0.0008(12) -0.0005(13) C34 0.0243(16) 0.0195(18) 0.0178(16) 0.0005(13) 0.0057(12) 0.0020(13) C35 0.0198(15) 0.0206(18) 0.0118(14) -0.0004(12) 0.0012(11) -0.0022(12) C36 0.0238(16) 0.0185(18) 0.0165(15) 0.0004(13) 0.0002(12) 0.0003(13) C37 0.0374(19) 0.0189(19) 0.0150(15) -0.0005(13) -0.0013(14) -0.0026(15) C38 0.0251(15) 0.0146(17) 0.0125(14) 0.0024(11) 0.0019(12) -0.0005(12) C39 0.041(2) 0.0207(19) 0.0196(17) 0.0015(14) 0.0046(14) 0.0046(15) C40 0.0224(15) 0.0181(18) 0.0169(15) 0.0016(12) 0.0050(12) 0.0029(13) C41 0.0295(17) 0.0162(17) 0.0145(15) 0.0006(12) 0.0001(12) 0.0058(13) C42 0.0207(15) 0.0193(18) 0.0120(14) -0.0007(12) -0.0005(11) -0.0014(12) C43 0.0273(16) 0.0168(17) 0.0148(15) -0.0026(12) 0.0016(12) 0.0007(13) C44 0.0376(19) 0.0218(19) 0.0165(16) 0.0006(13) 0.0035(14) -0.0005(15) C45 0.0290(17) 0.0168(17) 0.0126(15) -0.0005(12) 0.0007(12) 0.0033(13) N1 0.0444(18) 0.0176(16) 0.0224(15) -0.0020(12) -0.0004(13) -0.0057(13) N2 0.0490(19) 0.0272(18) 0.0180(14) -0.0011(12) -0.0007(13) -0.0028(15) N3 0.0513(19) 0.0261(18) 0.0162(14) -0.0004(12) 0.0016(13) -0.0047(14) N4 0.0367(16) 0.0195(16) 0.0179(14) 0.0009(11) 0.0018(12) -0.0034(13) N5 0.0349(16) 0.0186(16) 0.0187(14) 0.0010(11) 0.0025(12) -0.0022(12) N6 0.0412(17) 0.0252(17) 0.0180(14) 0.0034(12) -0.0035(12) -0.0086(14) N7 0.0382(16) 0.0217(16) 0.0152(13) 0.0019(11) 0.0016(12) 0.0030(13) N8 0.057(2) 0.0220(17) 0.0199(15) 0.0011(12) 0.0007(14) 0.0017(15) N9 0.066(2) 0.0239(19) 0.0217(16) 0.0029(13) -0.0024(15) 0.0044(16) N10 0.064(2) 0.0158(16) 0.0232(16) 0.0023(12) -0.0006(15) 0.0051(15) N11 0.055(2) 0.0286(18) 0.0162(14) -0.0013(12) -0.0038(13) 0.0092(15) N12 0.0361(16) 0.0221(17) 0.0200(14) -0.0014(11) 0.0055(12) 0.0007(13) N13 0.0469(18) 0.0148(15) 0.0234(15) 0.0002(12) 0.0064(13) 0.0048(13) N14 0.0413(17) 0.0267(18) 0.0194(15) -0.0002(12) 0.0068(13) 0.0033(14) N15 0.0438(17) 0.0221(17) 0.0184(14) -0.0019(12) 0.0062(12) 0.0021(13) N16 0.0350(15) 0.0200(16) 0.0150(13) 0.0014(11) 0.0023(11) 0.0009(12) N17 0.0414(17) 0.0254(17) 0.0204(15) 0.0035(12) 0.0101(13) 0.0068(14) N18 0.0340(15) 0.0222(16) 0.0163(13) -0.0015(11) 0.0021(11) 0.0017(12) O1 0.0249(12) 0.0442(17) 0.0144(11) 0.0019(10) -0.0022(9) -0.0012(11) O2 0.0215(11) 0.0457(17) 0.0174(12) 0.0000(10) 0.0034(9) 0.0010(11) O3 0.087(2) 0.0306(17) 0.0378(16) 0.0146(13) 0.0347(16) 0.0133(16) O4 0.0475(15) 0.0207(14) 0.0263(13) 0.0019(10) 0.0061(11) 0.0099(11) O5 0.0255(12) 0.0449(17) 0.0167(12) -0.0019(10) 0.0055(9) -0.0014(11) O6 0.0239(12) 0.0473(17) 0.0179(12) -0.0032(11) 0.0023(9) -0.0043(11) O7 0.200(5) 0.045(2) 0.0358(18) 0.0244(16) 0.060(2) 0.063(3) O8 0.092(2) 0.0299(17) 0.0281(15) 0.0071(12) 0.0200(15) 0.0275(16) O9 0.0236(12) 0.0379(16) 0.0141(11) 0.0012(10) -0.0016(9) 0.0015(10) O10 0.0269(12) 0.0405(16) 0.0167(12) -0.0001(10) 0.0036(9) -0.0005(11) O11 0.076(2) 0.0305(17) 0.0236(14) -0.0094(11) -0.0148(14) 0.0122(14) O12 0.0667(19) 0.0244(15) 0.0225(13) -0.0026(11) -0.0045(12) 0.0177(13) _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 N12 1.976(3) . ? Zn1 O2 1.980(2) . ? Zn1 O6 1.983(2) 3_665 ? Zn1 N4 2.005(3) . ? Zn2 O10 1.980(2) . ? Zn2 N5 1.986(3) 4_575 ? Zn2 N7 2.004(3) 4_565 ? Zn2 O5 2.015(2) . ? Zn3 N18 1.965(3) . ? Zn3 O1 1.972(2) . ? Zn3 N16 2.000(3) 2_755 ? Zn3 O9 2.003(2) 3_765 ? C1 C2 1.380(5) . ? C1 C6 1.394(5) . ? C1 H1 0.9300 . ? C2 C3 1.371(5) . ? C2 H2 0.9300 . ? C3 C4 1.402(5) . ? C3 H3 0.9300 . ? C4 C5 1.394(5) . ? C4 C8 1.457(5) . ? C5 C6 1.384(5) . ? C5 H5 0.9300 . ? C6 C7 1.475(4) . ? C7 N1 1.328(4) . ? C7 N4 1.342(4) . ? C8 C9 1.359(5) . ? C8 N6 1.380(4) . ? C9 N5 1.374(4) . ? C9 H9 0.9300 . ? C10 N5 1.317(4) . ? C10 N6 1.334(5) . ? C10 H10 0.9300 . ? C11 C12 1.378(5) . ? C11 C16 1.392(5) . ? C11 H11 0.9300 . ? C12 C13 1.384(5) . ? C12 H12 0.9300 . ? C13 C14 1.397(5) . ? C13 H13 0.9300 . ? C14 C15 1.381(5) . ? C14 C17 1.467(4) . ? C15 C16 1.400(4) . ? C15 H15 0.9300 . ? C16 C18 1.467(5) . ? C17 N10 1.324(4) . ? C17 N7 1.338(4) . ? C18 C19 1.350(5) . ? C18 N11 1.380(4) . ? C19 N12 1.377(4) . ? C19 H19 0.9300 . ? C20 N11 1.321(5) . ? C20 N12 1.332(4) . ? C20 H20 0.9300 . ? C21 C22 1.370(5) . ? C21 C26 1.395(5) . ? C21 H21 0.9300 . ? C22 C23 1.388(5) . ? C22 H22 0.9300 . ? C23 C24 1.390(5) . ? C23 H23 0.9300 . ? C24 C25 1.385(5) . ? C24 C27 1.471(4) . ? C25 C26 1.394(4) . ? C25 H25 0.9300 . ? C26 C28 1.460(5) . ? C27 N13 1.324(4) . ? C27 N16 1.333(4) . ? C28 C29 1.353(5) . ? C28 N17 1.374(4) . ? C29 N18 1.383(4) . ? C29 H29 0.9300 . ? C30 N18 1.320(4) . ? C30 N17 1.329(4) . ? C30 H30 0.9300 . ? C31 C32 1.387(4) . ? C31 C36 1.396(4) . ? C31 H31 0.9300 . ? C32 C33 1.395(4) . ? C32 C40 1.520(4) . ? C33 C34 1.395(4) . ? C33 C39 1.489(5) . ? C34 C35 1.382(4) . ? C34 H34 0.9300 . ? C35 C36 1.398(4) . ? C35 C38 1.515(4) . ? C36 C37 1.493(5) . ? C37 O3 1.205(4) . ? C37 O4 1.323(4) . ? C38 O2 1.254(4) . ? C38 O1 1.255(4) . ? C39 O7 1.189(4) . ? C39 O8 1.301(4) . ? C40 O5 1.247(4) . ? C40 O6 1.255(4) . ? C41 C42 1.391(4) . ? C41 C43 1.394(4) 3_764 ? C41 H41 0.9300 . ? C42 C43 1.395(4) . ? C42 C45 1.517(4) . ? C43 C41 1.394(4) 3_764 ? C43 C44 1.482(5) . ? C44 O11 1.202(4) . ? C44 O12 1.325(4) . ? C45 O9 1.249(4) . ? C45 O10 1.261(4) . ? N1 N2 1.347(4) . ? N1 H1A 0.8600 . ? N2 N3 1.307(4) . ? N3 N4 1.357(4) . ? N5 Zn2 1.986(3) 4_576 ? N6 H6 0.8600 . ? N7 N8 1.361(4) . ? N7 Zn2 2.004(3) 4_566 ? N8 N9 1.298(4) . ? N9 N10 1.350(4) . ? N10 H10A 0.8600 . ? N11 H11A 0.8600 . ? N13 N14 1.346(4) . ? N13 H13A 0.8600 . ? N14 N15 1.298(4) . ? N15 N16 1.355(4) . ? N16 Zn3 2.000(3) 2_745 ? N17 H17 0.8600 . ? O6 Zn1 1.983(2) 3_665 ? O9 Zn3 2.003(2) 3_765 ? 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 N12 Zn1 O2 111.92(11) . . ? N12 Zn1 O6 116.81(11) . 3_665 ? O2 Zn1 O6 98.09(10) . 3_665 ? N12 Zn1 N4 108.41(12) . . ? O2 Zn1 N4 121.66(11) . . ? O6 Zn1 N4 99.40(11) 3_665 . ? O10 Zn2 N5 114.68(11) . 4_575 ? O10 Zn2 N7 101.91(11) . 4_565 ? N5 Zn2 N7 108.51(12) 4_575 4_565 ? O10 Zn2 O5 92.97(9) . . ? N5 Zn2 O5 110.68(11) 4_575 . ? N7 Zn2 O5 126.79(11) 4_565 . ? N18 Zn3 O1 113.92(11) . . ? N18 Zn3 N16 109.27(11) . 2_755 ? O1 Zn3 N16 99.28(11) . 2_755 ? N18 Zn3 O9 113.02(11) . 3_765 ? O1 Zn3 O9 95.40(9) . 3_765 ? N16 Zn3 O9 124.08(10) 2_755 3_765 ? C2 C1 C6 118.9(3) . . ? C2 C1 H1 120.5 . . ? C6 C1 H1 120.5 . . ? C3 C2 C1 121.7(3) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 118.9(3) . . ? C5 C4 C8 119.5(3) . . ? C3 C4 C8 121.6(3) . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 C7 120.2(3) . . ? C1 C6 C7 119.6(3) . . ? N1 C7 N4 110.0(3) . . ? N1 C7 C6 125.8(3) . . ? N4 C7 C6 124.1(3) . . ? C9 C8 N6 104.7(3) . . ? C9 C8 C4 131.5(3) . . ? N6 C8 C4 123.6(3) . . ? C8 C9 N5 110.0(3) . . ? C8 C9 H9 125.0 . . ? N5 C9 H9 125.0 . . ? N5 C10 N6 110.6(3) . . ? N5 C10 H10 124.7 . . ? N6 C10 H10 124.7 . . ? C12 C11 C16 120.3(3) . . ? C12 C11 H11 119.8 . . ? C16 C11 H11 119.8 . . ? C11 C12 C13 121.2(3) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C14 118.9(3) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 120.1(3) . . ? C15 C14 C17 118.8(3) . . ? C13 C14 C17 121.2(3) . . ? C14 C15 C16 120.9(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C11 C16 C15 118.6(3) . . ? C11 C16 C18 122.9(3) . . ? C15 C16 C18 118.5(3) . . ? N10 C17 N7 109.5(3) . . ? N10 C17 C14 125.8(3) . . ? N7 C17 C14 124.6(3) . . ? C19 C18 N11 105.0(3) . . ? C19 C18 C16 131.1(3) . . ? N11 C18 C16 123.9(3) . . ? C18 C19 N12 110.5(3) . . ? C18 C19 H19 124.7 . . ? N12 C19 H19 124.7 . . ? N11 C20 N12 111.2(3) . . ? N11 C20 H20 124.4 . . ? N12 C20 H20 124.4 . . ? C22 C21 C26 121.0(3) . . ? C22 C21 H21 119.5 . . ? C26 C21 H21 119.5 . . ? C21 C22 C23 120.7(3) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 C24 119.0(3) . . ? C22 C23 H23 120.5 . . ? C24 C23 H23 120.5 . . ? C25 C24 C23 120.3(3) . . ? C25 C24 C27 118.4(3) . . ? C23 C24 C27 121.3(3) . . ? C24 C25 C26 120.6(3) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 118.3(3) . . ? C25 C26 C28 118.5(3) . . ? C21 C26 C28 123.2(3) . . ? N13 C27 N16 109.8(3) . . ? N13 C27 C24 125.8(3) . . ? N16 C27 C24 124.2(3) . . ? C29 C28 N17 105.6(3) . . ? C29 C28 C26 130.6(3) . . ? N17 C28 C26 123.7(3) . . ? C28 C29 N18 109.6(3) . . ? C28 C29 H29 125.2 . . ? N18 C29 H29 125.2 . . ? N18 C30 N17 111.1(3) . . ? N18 C30 H30 124.5 . . ? N17 C30 H30 124.5 . . ? C32 C31 C36 121.8(3) . . ? C32 C31 H31 119.1 . . ? C36 C31 H31 119.1 . . ? C31 C32 C33 118.5(3) . . ? C31 C32 C40 116.6(3) . . ? C33 C32 C40 124.7(3) . . ? C32 C33 C34 120.1(3) . . ? C32 C33 C39 119.7(3) . . ? C34 C33 C39 120.2(3) . . ? C35 C34 C33 121.1(3) . . ? C35 C34 H34 119.4 . . ? C33 C34 H34 119.4 . . ? C34 C35 C36 119.3(3) . . ? C34 C35 C38 117.1(3) . . ? C36 C35 C38 123.6(3) . . ? C31 C36 C35 119.2(3) . . ? C31 C36 C37 120.4(3) . . ? C35 C36 C37 119.9(3) . . ? O3 C37 O4 123.2(3) . . ? O3 C37 C36 121.5(3) . . ? O4 C37 C36 115.2(3) . . ? O2 C38 O1 121.3(3) . . ? O2 C38 C35 117.1(3) . . ? O1 C38 C35 121.4(3) . . ? O7 C39 O8 121.9(3) . . ? O7 C39 C33 122.0(3) . . ? O8 C39 C33 116.1(3) . . ? O5 C40 O6 120.5(3) . . ? O5 C40 C32 118.7(3) . . ? O6 C40 C32 120.4(3) . . ? C42 C41 C43 121.6(3) . 3_764 ? C42 C41 H41 119.2 . . ? C43 C41 H41 119.2 3_764 . ? C41 C42 C43 119.2(3) . . ? C41 C42 C45 116.4(3) . . ? C43 C42 C45 124.4(3) . . ? C41 C43 C42 119.3(3) 3_764 . ? C41 C43 C44 120.9(3) 3_764 . ? C42 C43 C44 119.8(3) . . ? O11 C44 O12 123.1(3) . . ? O11 C44 C43 122.3(3) . . ? O12 C44 C43 114.6(3) . . ? O9 C45 O10 121.3(3) . . ? O9 C45 C42 118.8(3) . . ? O10 C45 C42 119.7(3) . . ? C7 N1 N2 105.7(3) . . ? C7 N1 H1A 127.1 . . ? N2 N1 H1A 127.1 . . ? N3 N2 N1 110.2(3) . . ? N2 N3 N4 107.8(3) . . ? C7 N4 N3 106.2(3) . . ? C7 N4 Zn1 137.3(2) . . ? N3 N4 Zn1 116.5(2) . . ? C10 N5 C9 106.1(3) . . ? C10 N5 Zn2 129.9(2) . 4_576 ? C9 N5 Zn2 121.9(2) . 4_576 ? C10 N6 C8 108.6(3) . . ? C10 N6 H6 125.7 . . ? C8 N6 H6 125.7 . . ? C17 N7 N8 106.3(3) . . ? C17 N7 Zn2 139.3(2) . 4_566 ? N8 N7 Zn2 114.2(2) . 4_566 ? N9 N8 N7 108.1(3) . . ? N8 N9 N10 109.7(3) . . ? C17 N10 N9 106.3(3) . . ? C17 N10 H10A 126.8 . . ? N9 N10 H10A 126.8 . . ? C20 N11 C18 108.4(3) . . ? C20 N11 H11A 125.8 . . ? C18 N11 H11A 125.8 . . ? C20 N12 C19 104.8(3) . . ? C20 N12 Zn1 130.3(3) . . ? C19 N12 Zn1 121.6(2) . . ? C27 N13 N14 106.0(3) . . ? C27 N13 H13A 127.0 . . ? N14 N13 H13A 127.0 . . ? N15 N14 N13 109.8(3) . . ? N14 N15 N16 108.0(3) . . ? C27 N16 N15 106.3(3) . . ? C27 N16 Zn3 137.7(2) . 2_745 ? N15 N16 Zn3 115.5(2) . 2_745 ? C30 N17 C28 108.2(3) . . ? C30 N17 H17 125.9 . . ? C28 N17 H17 125.9 . . ? C30 N18 C29 105.6(3) . . ? C30 N18 Zn3 130.2(2) . . ? C29 N18 Zn3 122.1(2) . . ? C38 O1 Zn3 136.8(2) . . ? C38 O2 Zn1 114.6(2) . . ? C40 O5 Zn2 108.5(2) . . ? C40 O6 Zn1 140.4(2) . 3_665 ? C45 O9 Zn3 108.6(2) . 3_765 ? C45 O10 Zn2 139.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.3(6) . . . . ? C1 C2 C3 C4 0.5(6) . . . . ? C2 C3 C4 C5 0.3(6) . . . . ? C2 C3 C4 C8 -176.9(4) . . . . ? C3 C4 C5 C6 -0.2(5) . . . . ? C8 C4 C5 C6 177.1(3) . . . . ? C4 C5 C6 C1 -0.7(5) . . . . ? C4 C5 C6 C7 180.0(3) . . . . ? C2 C1 C6 C5 1.4(5) . . . . ? C2 C1 C6 C7 -179.2(3) . . . . ? C5 C6 C7 N1 31.6(5) . . . . ? C1 C6 C7 N1 -147.7(4) . . . . ? C5 C6 C7 N4 -145.6(3) . . . . ? C1 C6 C7 N4 35.1(5) . . . . ? C5 C4 C8 C9 3.7(6) . . . . ? C3 C4 C8 C9 -179.1(4) . . . . ? C5 C4 C8 N6 -170.6(3) . . . . ? C3 C4 C8 N6 6.6(5) . . . . ? N6 C8 C9 N5 1.8(4) . . . . ? C4 C8 C9 N5 -173.3(3) . . . . ? C16 C11 C12 C13 0.5(6) . . . . ? C11 C12 C13 C14 -0.9(5) . . . . ? C12 C13 C14 C15 0.8(5) . . . . ? C12 C13 C14 C17 -179.0(3) . . . . ? C13 C14 C15 C16 -0.3(5) . . . . ? C17 C14 C15 C16 179.4(3) . . . . ? C12 C11 C16 C15 -0.1(5) . . . . ? C12 C11 C16 C18 -179.9(3) . . . . ? C14 C15 C16 C11 0.0(5) . . . . ? C14 C15 C16 C18 179.8(3) . . . . ? C15 C14 C17 N10 30.6(5) . . . . ? C13 C14 C17 N10 -149.7(4) . . . . ? C15 C14 C17 N7 -146.5(4) . . . . ? C13 C14 C17 N7 33.2(5) . . . . ? C11 C16 C18 C19 179.9(4) . . . . ? C15 C16 C18 C19 0.2(6) . . . . ? C11 C16 C18 N11 1.5(6) . . . . ? C15 C16 C18 N11 -178.3(3) . . . . ? N11 C18 C19 N12 1.5(4) . . . . ? C16 C18 C19 N12 -177.1(4) . . . . ? C26 C21 C22 C23 -0.2(6) . . . . ? C21 C22 C23 C24 0.0(5) . . . . ? C22 C23 C24 C25 -0.3(5) . . . . ? C22 C23 C24 C27 177.4(3) . . . . ? C23 C24 C25 C26 0.8(5) . . . . ? C27 C24 C25 C26 -176.9(3) . . . . ? C24 C25 C26 C21 -1.0(5) . . . . ? C24 C25 C26 C28 -178.9(3) . . . . ? C22 C21 C26 C25 0.7(6) . . . . ? C22 C21 C26 C28 178.5(3) . . . . ? C25 C24 C27 N13 -34.8(5) . . . . ? C23 C24 C27 N13 147.6(4) . . . . ? C25 C24 C27 N16 141.3(3) . . . . ? C23 C24 C27 N16 -36.4(5) . . . . ? C25 C26 C28 C29 -7.2(6) . . . . ? C21 C26 C28 C29 175.0(4) . . . . ? C25 C26 C28 N17 168.9(3) . . . . ? C21 C26 C28 N17 -8.9(6) . . . . ? N17 C28 C29 N18 -1.4(4) . . . . ? C26 C28 C29 N18 175.3(3) . . . . ? C36 C31 C32 C33 1.5(5) . . . . ? C36 C31 C32 C40 -174.2(3) . . . . ? C31 C32 C33 C34 -0.2(5) . . . . ? C40 C32 C33 C34 175.2(3) . . . . ? C31 C32 C33 C39 -178.8(3) . . . . ? C40 C32 C33 C39 -3.4(5) . . . . ? C32 C33 C34 C35 -1.5(5) . . . . ? C39 C33 C34 C35 177.1(3) . . . . ? C33 C34 C35 C36 1.9(5) . . . . ? C33 C34 C35 C38 -179.4(3) . . . . ? C32 C31 C36 C35 -1.2(5) . . . . ? C32 C31 C36 C37 171.3(3) . . . . ? C34 C35 C36 C31 -0.5(5) . . . . ? C38 C35 C36 C31 -179.2(3) . . . . ? C34 C35 C36 C37 -173.0(3) . . . . ? C38 C35 C36 C37 8.3(5) . . . . ? C31 C36 C37 O3 -155.6(3) . . . . ? C35 C36 C37 O3 16.8(5) . . . . ? C31 C36 C37 O4 22.4(4) . . . . ? C35 C36 C37 O4 -165.2(3) . . . . ? C34 C35 C38 O2 69.7(4) . . . . ? C36 C35 C38 O2 -111.7(4) . . . . ? C34 C35 C38 O1 -105.2(4) . . . . ? C36 C35 C38 O1 73.5(4) . . . . ? C32 C33 C39 O7 -1.1(6) . . . . ? C34 C33 C39 O7 -179.7(4) . . . . ? C32 C33 C39 O8 178.3(3) . . . . ? C34 C33 C39 O8 -0.2(5) . . . . ? C31 C32 C40 O5 -78.9(4) . . . . ? C33 C32 C40 O5 105.6(4) . . . . ? C31 C32 C40 O6 93.5(4) . . . . ? C33 C32 C40 O6 -81.9(4) . . . . ? C43 C41 C42 C43 0.4(5) 3_764 . . . ? C43 C41 C42 C45 177.2(3) 3_764 . . . ? C41 C42 C43 C41 -0.4(5) . . . 3_764 ? C45 C42 C43 C41 -176.9(3) . . . 3_764 ? C41 C42 C43 C44 -177.3(3) . . . . ? C45 C42 C43 C44 6.2(5) . . . . ? C41 C43 C44 O11 -162.2(3) 3_764 . . . ? C42 C43 C44 O11 14.7(5) . . . . ? C41 C43 C44 O12 18.4(5) 3_764 . . . ? C42 C43 C44 O12 -164.8(3) . . . . ? C41 C42 C45 O9 76.7(4) . . . . ? C43 C42 C45 O9 -106.8(4) . . . . ? C41 C42 C45 O10 -98.4(4) . . . . ? C43 C42 C45 O10 78.2(4) . . . . ? N4 C7 N1 N2 -0.6(4) . . . . ? C6 C7 N1 N2 -178.1(3) . . . . ? C7 N1 N2 N3 0.3(4) . . . . ? N1 N2 N3 N4 0.2(4) . . . . ? N1 C7 N4 N3 0.7(4) . . . . ? C6 C7 N4 N3 178.3(3) . . . . ? N1 C7 N4 Zn1 -177.8(3) . . . . ? C6 C7 N4 Zn1 -0.2(6) . . . . ? N2 N3 N4 C7 -0.6(4) . . . . ? N2 N3 N4 Zn1 178.3(2) . . . . ? N12 Zn1 N4 C7 150.9(3) . . . . ? O2 Zn1 N4 C7 19.0(4) . . . . ? O6 Zn1 N4 C7 -86.7(4) 3_665 . . . ? N12 Zn1 N4 N3 -27.5(3) . . . . ? O2 Zn1 N4 N3 -159.4(2) . . . . ? O6 Zn1 N4 N3 94.9(2) 3_665 . . . ? N6 C10 N5 C9 1.0(4) . . . . ? N6 C10 N5 Zn2 -162.7(3) . . . 4_576 ? C8 C9 N5 C10 -1.8(4) . . . . ? C8 C9 N5 Zn2 163.5(2) . . . 4_576 ? N5 C10 N6 C8 0.2(4) . . . . ? C9 C8 N6 C10 -1.2(4) . . . . ? C4 C8 N6 C10 174.4(3) . . . . ? N10 C17 N7 N8 0.0(4) . . . . ? C14 C17 N7 N8 177.5(3) . . . . ? N10 C17 N7 Zn2 175.9(3) . . . 4_566 ? C14 C17 N7 Zn2 -6.6(6) . . . 4_566 ? C17 N7 N8 N9 0.0(4) . . . . ? Zn2 N7 N8 N9 -177.1(2) 4_566 . . . ? N7 N8 N9 N10 0.0(4) . . . . ? N7 C17 N10 N9 0.0(4) . . . . ? C14 C17 N10 N9 -177.5(3) . . . . ? N8 N9 N10 C17 0.0(4) . . . . ? N12 C20 N11 C18 1.1(5) . . . . ? C19 C18 N11 C20 -1.6(4) . . . . ? C16 C18 N11 C20 177.2(4) . . . . ? N11 C20 N12 C19 -0.1(4) . . . . ? N11 C20 N12 Zn1 -159.3(3) . . . . ? C18 C19 N12 C20 -0.9(4) . . . . ? C18 C19 N12 Zn1 160.5(2) . . . . ? O2 Zn1 N12 C20 143.8(3) . . . . ? O6 Zn1 N12 C20 -104.3(3) 3_665 . . . ? N4 Zn1 N12 C20 6.9(3) . . . . ? O2 Zn1 N12 C19 -12.5(3) . . . . ? O6 Zn1 N12 C19 99.5(3) 3_665 . . . ? N4 Zn1 N12 C19 -149.4(3) . . . . ? N16 C27 N13 N14 0.4(4) . . . . ? C24 C27 N13 N14 176.9(3) . . . . ? C27 N13 N14 N15 -0.6(4) . . . . ? N13 N14 N15 N16 0.6(4) . . . . ? N13 C27 N16 N15 0.0(4) . . . . ? C24 C27 N16 N15 -176.6(3) . . . . ? N13 C27 N16 Zn3 -171.3(3) . . . 2_745 ? C24 C27 N16 Zn3 12.1(6) . . . 2_745 ? N14 N15 N16 C27 -0.4(4) . . . . ? N14 N15 N16 Zn3 173.2(2) . . . 2_745 ? N18 C30 N17 C28 -1.1(4) . . . . ? C29 C28 N17 C30 1.5(4) . . . . ? C26 C28 N17 C30 -175.5(3) . . . . ? N17 C30 N18 C29 0.2(4) . . . . ? N17 C30 N18 Zn3 163.7(2) . . . . ? C28 C29 N18 C30 0.8(4) . . . . ? C28 C29 N18 Zn3 -164.4(2) . . . . ? O1 Zn3 N18 C30 102.2(3) . . . . ? N16 Zn3 N18 C30 -7.8(3) 2_755 . . . ? O9 Zn3 N18 C30 -150.3(3) 3_765 . . . ? O1 Zn3 N18 C29 -96.6(3) . . . . ? N16 Zn3 N18 C29 153.4(3) 2_755 . . . ? O9 Zn3 N18 C29 10.9(3) 3_765 . . . ? O2 C38 O1 Zn3 -176.3(2) . . . . ? C35 C38 O1 Zn3 -1.7(5) . . . . ? N18 Zn3 O1 C38 -52.8(4) . . . . ? N16 Zn3 O1 C38 63.2(3) 2_755 . . . ? O9 Zn3 O1 C38 -171.0(3) 3_765 . . . ? O1 C38 O2 Zn1 -3.3(4) . . . . ? C35 C38 O2 Zn1 -178.2(2) . . . . ? N12 Zn1 O2 C38 -55.9(3) . . . . ? O6 Zn1 O2 C38 -179.2(2) 3_665 . . . ? N4 Zn1 O2 C38 74.5(3) . . . . ? O6 C40 O5 Zn2 2.6(4) . . . . ? C32 C40 O5 Zn2 175.0(2) . . . . ? O10 Zn2 O5 C40 -173.8(2) . . . . ? N5 Zn2 O5 C40 68.4(2) 4_575 . . . ? N7 Zn2 O5 C40 -66.5(3) 4_565 . . . ? O5 C40 O6 Zn1 -164.7(3) . . . 3_665 ? C32 C40 O6 Zn1 23.0(5) . . . 3_665 ? O10 C45 O9 Zn3 -1.9(4) . . . 3_765 ? C42 C45 O9 Zn3 -176.9(2) . . . 3_765 ? O9 C45 O10 Zn2 174.6(2) . . . . ? C42 C45 O10 Zn2 -10.5(5) . . . . ? N5 Zn2 O10 C45 -44.6(4) 4_575 . . . ? N7 Zn2 O10 C45 72.4(3) 4_565 . . . ? O5 Zn2 O10 C45 -159.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.819 _refine_diff_density_min -1.092 _refine_diff_density_rms 0.204 _database_code_depnum_ccdc_archive 'CCDC 920976'