# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email jicanmail@163.com loop_ _publ_author_name 'Shuang-Quan Zang' 'Can Ji' data_c _database_code_depnum_ccdc_archive 'CCDC 857237' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H30 N8 O6 Zn, 3(H2 O)' _chemical_formula_sum 'C30 H36 N8 O9 Zn' _chemical_formula_weight 718.04 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 '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 25.804(4) _cell_length_b 9.7779(6) _cell_length_c 18.861(10) _cell_angle_alpha 90.00 _cell_angle_beta 136.399(12) _cell_angle_gamma 90.00 _cell_volume 3281.8(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296 _cell_measurement_reflns_used 3741 _cell_measurement_theta_min 3.1260 _cell_measurement_theta_max 29.1348 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8542 _exptl_absorpt_correction_T_max 0.8808 _exptl_absorpt_process_details SADABS(2009) _exptl_special_details ; ? ; _diffrn_ambient_temperature 296 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7798 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2883 _reflns_number_gt 2420 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of 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^)+(0.1530P)^2^+12.6341P] 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 2883 _refine_ls_number_parameters 219 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.2404 _refine_ls_wR_factor_gt 0.2273 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.0000 0.15565(8) -0.2500 0.0391(4) Uani 1 2 d SD . . O1W O 0.04813(19) 0.3188(3) -0.2717(3) 0.0333(8) Uani 1 1 d D . . H1WA H 0.0355 0.3147 -0.3273 0.050 Uiso 1 1 d RD . . H1WB H 0.0429 0.3993 -0.2617 0.050 Uiso 1 1 d RD . . O2 O 0.3917(2) 0.1761(4) 0.5702(3) 0.0445(10) Uani 1 1 d . . . O1 O 0.43887(19) 0.1111(4) 0.5135(3) 0.0385(8) Uani 1 1 d . . . N2 N 0.2147(2) 0.2578(4) 0.0703(3) 0.0311(9) Uani 1 1 d . . . N1 N 0.1125(2) 0.1737(4) -0.0819(3) 0.0321(9) Uani 1 1 d . . . C1 C 0.3903(2) 0.1702(4) 0.5028(3) 0.0240(9) Uani 1 1 d D . . C5 C 0.2000(2) 0.3470(4) 0.2098(3) 0.0257(10) Uani 1 1 d . . . H5 H 0.1586 0.3867 0.1468 0.031 Uiso 1 1 calc R . . C4 C 0.2654(2) 0.3243(4) 0.2351(3) 0.0262(9) Uani 1 1 d . . . C7 C 0.2585(2) 0.2583(4) 0.3724(3) 0.0220(9) Uani 1 1 d . . . H7 H 0.2562 0.2380 0.4182 0.026 Uiso 1 1 calc R . . C2 C 0.3246(2) 0.2348(4) 0.4005(3) 0.0217(8) Uani 1 1 d D . . C13 C 0.1492(2) 0.2848(5) -0.0268(3) 0.0309(10) Uani 1 1 d . . . H13 H 0.1315 0.3729 -0.0525 0.037 Uiso 1 1 calc R . . C6 C 0.1953(2) 0.3125(4) 0.2753(3) 0.0240(9) Uani 1 1 d . . . C3 C 0.3276(2) 0.2661(4) 0.3310(3) 0.0245(9) Uani 1 1 d . . . H3 H 0.3711 0.2482 0.3486 0.029 Uiso 1 1 calc R . . C12 C 0.2666(3) 0.3509(5) 0.1573(4) 0.0348(11) Uani 1 1 d . . . H12A H 0.2520 0.4448 0.1335 0.042 Uiso 1 1 calc R . . H12B H 0.3170 0.3373 0.1891 0.042 Uiso 1 1 calc R . . C8 C 0.1220(2) 0.3258(4) 0.2435(4) 0.0269(9) Uani 1 1 d . . . H8A H 0.1320 0.3604 0.3007 0.032 Uiso 1 1 calc R . . H8B H 0.0890 0.3899 0.1869 0.032 Uiso 1 1 calc R . . C15 C 0.2196(4) 0.1168(7) 0.0773(4) 0.075(2) Uani 1 1 d . . . H15 H 0.2586 0.0649 0.1348 0.090 Uiso 1 1 calc R . . C14 C 0.1554(4) 0.0692(6) -0.0174(4) 0.068(2) Uani 1 1 d . . . H14 H 0.1432 -0.0228 -0.0347 0.082 Uiso 1 1 calc R . . O2W O 0.0000 0.4545(4) 0.2500 0.0285(10) Uani 1 2 d S . . H2WA H 0.0273 0.4051 0.3024 0.031(13) Uiso 1 1 d R . . O3W O 0.5122(2) 0.1503(3) 0.4614(3) 0.0401(9) Uani 1 1 d D . . H3WA H 0.4864 0.1461 0.4739 0.060 Uiso 1 1 d RD . . H3WB H 0.5328 0.0733 0.4755 0.060 Uiso 1 1 d RD . . N3 N 0.08554(19) 0.1912(4) 0.2120(3) 0.0239(8) Uani 1 1 d . . . C11 C 0.0687(2) 0.1234(5) 0.2549(3) 0.0267(9) Uani 1 1 d . . . H11 H 0.0782 0.1564 0.3097 0.032 Uiso 1 1 calc R . . C9 C 0.0639(3) 0.1106(5) 0.1348(3) 0.0356(11) Uani 1 1 d . . . H9 H 0.0688 0.1300 0.0916 0.043 Uiso 1 1 calc R . . N4 N 0.0372(2) 0.0051(4) 0.2104(3) 0.0279(8) Uani 1 1 d . . . C10 C 0.0338(3) -0.0039(5) 0.1345(4) 0.0355(11) Uani 1 1 d . . . H10 H 0.0139 -0.0772 0.0897 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0442(6) 0.0362(6) 0.0391(6) 0.000 0.0309(5) 0.000 O1W 0.0424(19) 0.0285(16) 0.0344(17) 0.0035(14) 0.0295(17) -0.0010(14) O2 0.0369(19) 0.072(3) 0.0215(16) 0.0138(16) 0.0201(16) 0.0237(17) O1 0.0343(18) 0.049(2) 0.0341(18) 0.0160(16) 0.0254(16) 0.0201(16) N2 0.031(2) 0.037(2) 0.0180(17) 0.0025(15) 0.0155(17) 0.0018(16) N1 0.032(2) 0.031(2) 0.0203(18) 0.0016(15) 0.0145(17) 0.0012(16) C1 0.022(2) 0.027(2) 0.016(2) 0.0014(16) 0.0115(18) 0.0018(16) C5 0.017(2) 0.027(2) 0.020(2) 0.0034(16) 0.0092(18) -0.0011(16) C4 0.023(2) 0.029(2) 0.015(2) 0.0003(16) 0.0100(18) -0.0048(17) C7 0.024(2) 0.0208(19) 0.024(2) -0.0009(16) 0.0179(18) -0.0003(16) C2 0.0187(19) 0.0207(19) 0.0167(18) -0.0003(15) 0.0099(17) 0.0004(16) C13 0.027(2) 0.033(2) 0.023(2) 0.0106(19) 0.0143(19) 0.0065(19) C6 0.0161(19) 0.0206(19) 0.023(2) -0.0010(16) 0.0105(18) -0.0007(16) C3 0.0175(19) 0.031(2) 0.0195(19) -0.0006(17) 0.0117(17) -0.0009(17) C12 0.027(2) 0.049(3) 0.022(2) 0.0024(19) 0.016(2) -0.006(2) C8 0.021(2) 0.022(2) 0.034(2) 0.0009(17) 0.019(2) -0.0007(16) C15 0.083(5) 0.039(3) 0.027(3) 0.009(2) 0.015(3) 0.026(3) C14 0.086(5) 0.030(3) 0.032(3) 0.002(2) 0.024(3) 0.007(3) O2W 0.039(2) 0.020(2) 0.021(2) 0.000 0.020(2) 0.000 O3W 0.050(2) 0.040(2) 0.042(2) 0.0063(14) 0.0372(19) 0.0064(15) N3 0.0223(18) 0.0237(17) 0.0244(18) 0.0007(15) 0.0165(16) 0.0002(14) C11 0.027(2) 0.028(2) 0.024(2) 0.0005(18) 0.018(2) 0.0014(18) C9 0.048(3) 0.039(3) 0.028(2) -0.007(2) 0.031(2) -0.013(2) N4 0.034(2) 0.0233(18) 0.0316(18) 0.0009(15) 0.0258(17) -0.0012(15) C10 0.047(3) 0.033(2) 0.031(2) -0.008(2) 0.029(2) -0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N4 2.233(4) 6 ? Zn1 N4 2.233(4) 5 ? Zn1 O1W 2.234(3) . ? Zn1 O1W 2.234(3) 2_554 ? Zn1 N1 2.276(4) . ? Zn1 N1 2.276(4) 2_554 ? O1W H1WA 0.8440 . ? O1W H1WB 0.8436 . ? O2 C1 1.248(6) . ? O1 C1 1.256(5) . ? N2 C13 1.341(6) . ? N2 C15 1.383(7) . ? N2 C12 1.459(6) . ? N1 C13 1.316(6) . ? N1 C14 1.342(7) . ? C1 C2 1.503(5) . ? C5 C6 1.367(6) . ? C5 C4 1.399(6) . ? C5 H5 0.9300 . ? C4 C3 1.402(6) . ? C4 C12 1.514(6) . ? C7 C2 1.389(6) . ? C7 C6 1.403(6) . ? C7 H7 0.9300 . ? C2 C3 1.403(6) . ? C13 H13 0.9300 . ? C6 C8 1.521(6) . ? C3 H3 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C8 N3 1.470(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C15 C14 1.366(9) . ? C15 H15 0.9300 . ? C14 H14 0.9300 . ? O2W H2WA 0.8356 . ? O3W H3WA 0.8525 . ? O3W H3WB 0.8450 . ? N3 C11 1.339(6) . ? N3 C9 1.370(6) . ? C11 N4 1.310(6) . ? C11 H11 0.9300 . ? C9 C10 1.360(7) . ? C9 H9 0.9300 . ? N4 C10 1.372(6) . ? N4 Zn1 2.233(4) 5 ? C10 H10 0.9300 . ? 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 N4 Zn1 N4 90.52(19) 6 5 ? N4 Zn1 O1W 90.61(13) 6 . ? N4 Zn1 O1W 173.94(12) 5 . ? N4 Zn1 O1W 173.94(13) 6 2_554 ? N4 Zn1 O1W 90.61(13) 5 2_554 ? O1W Zn1 O1W 88.90(18) . 2_554 ? N4 Zn1 N1 95.56(14) 6 . ? N4 Zn1 N1 90.70(14) 5 . ? O1W Zn1 N1 83.26(14) . . ? O1W Zn1 N1 90.38(14) 2_554 . ? N4 Zn1 N1 90.70(14) 6 2_554 ? N4 Zn1 N1 95.56(14) 5 2_554 ? O1W Zn1 N1 90.38(14) . 2_554 ? O1W Zn1 N1 83.26(14) 2_554 2_554 ? N1 Zn1 N1 171.1(2) . 2_554 ? Zn1 O1W H1WA 115.4 . . ? Zn1 O1W H1WB 115.2 . . ? H1WA O1W H1WB 110.0 . . ? C13 N2 C15 105.3(4) . . ? C13 N2 C12 129.5(4) . . ? C15 N2 C12 124.7(4) . . ? C13 N1 C14 105.2(4) . . ? C13 N1 Zn1 128.8(3) . . ? C14 N1 Zn1 125.9(3) . . ? O2 C1 O1 124.7(4) . . ? O2 C1 C2 117.5(4) . . ? O1 C1 C2 117.9(4) . . ? C6 C5 C4 121.7(4) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C4 C3 118.4(4) . . ? C5 C4 C12 120.6(4) . . ? C3 C4 C12 120.8(4) . . ? C2 C7 C6 120.4(4) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C2 C3 119.4(3) . . ? C7 C2 C1 119.5(4) . . ? C3 C2 C1 121.1(4) . . ? N1 C13 N2 113.0(4) . . ? N1 C13 H13 123.5 . . ? N2 C13 H13 123.5 . . ? C5 C6 C7 119.5(4) . . ? C5 C6 C8 121.4(4) . . ? C7 C6 C8 119.0(4) . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? N2 C12 C4 109.7(4) . . ? N2 C12 H12A 109.7 . . ? C4 C12 H12A 109.7 . . ? N2 C12 H12B 109.7 . . ? C4 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N3 C8 C6 109.4(3) . . ? N3 C8 H8A 109.8 . . ? C6 C8 H8A 109.8 . . ? N3 C8 H8B 109.8 . . ? C6 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C14 C15 N2 106.0(5) . . ? C14 C15 H15 127.0 . . ? N2 C15 H15 127.0 . . ? N1 C14 C15 110.5(5) . . ? N1 C14 H14 124.8 . . ? C15 C14 H14 124.8 . . ? H3WA O3W H3WB 107.9 . . ? C11 N3 C9 107.2(4) . . ? C11 N3 C8 126.3(4) . . ? C9 N3 C8 126.5(4) . . ? N4 C11 N3 111.9(4) . . ? N4 C11 H11 124.0 . . ? N3 C11 H11 124.0 . . ? C10 C9 N3 105.6(4) . . ? C10 C9 H9 127.2 . . ? N3 C9 H9 127.2 . . ? C11 N4 C10 105.4(4) . . ? C11 N4 Zn1 128.7(3) . 5 ? C10 N4 Zn1 125.8(3) . 5 ? C9 C10 N4 109.8(4) . . ? C9 C10 H10 125.1 . . ? N4 C10 H10 125.1 . . ? 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 N4 Zn1 N1 C13 134.9(4) 6 . . . ? N4 Zn1 N1 C13 -134.5(4) 5 . . . ? O1W Zn1 N1 C13 44.9(4) . . . . ? O1W Zn1 N1 C13 -43.9(4) 2_554 . . . ? N4 Zn1 N1 C14 -45.7(6) 6 . . . ? N4 Zn1 N1 C14 44.8(6) 5 . . . ? O1W Zn1 N1 C14 -135.7(6) . . . . ? O1W Zn1 N1 C14 135.5(6) 2_554 . . . ? C6 C5 C4 C3 -0.8(6) . . . . ? C6 C5 C4 C12 174.1(4) . . . . ? C6 C7 C2 C3 0.2(6) . . . . ? C6 C7 C2 C1 -177.0(4) . . . . ? O2 C1 C2 C7 -20.3(6) . . . . ? O1 C1 C2 C7 157.8(4) . . . . ? O2 C1 C2 C3 162.6(4) . . . . ? O1 C1 C2 C3 -19.3(6) . . . . ? C14 N1 C13 N2 1.1(6) . . . . ? Zn1 N1 C13 N2 -179.4(3) . . . . ? C15 N2 C13 N1 -0.5(6) . . . . ? C12 N2 C13 N1 -172.0(4) . . . . ? C4 C5 C6 C7 2.8(6) . . . . ? C4 C5 C6 C8 -174.5(4) . . . . ? C2 C7 C6 C5 -2.5(6) . . . . ? C2 C7 C6 C8 174.9(4) . . . . ? C5 C4 C3 C2 -1.5(6) . . . . ? C12 C4 C3 C2 -176.4(4) . . . . ? C7 C2 C3 C4 1.8(6) . . . . ? C1 C2 C3 C4 179.0(4) . . . . ? C13 N2 C12 C4 110.4(5) . . . . ? C15 N2 C12 C4 -59.7(7) . . . . ? C5 C4 C12 N2 -64.1(6) . . . . ? C3 C4 C12 N2 110.7(5) . . . . ? C5 C6 C8 N3 99.4(5) . . . . ? C7 C6 C8 N3 -77.9(5) . . . . ? C13 N2 C15 C14 -0.3(8) . . . . ? C12 N2 C15 C14 171.7(6) . . . . ? C13 N1 C14 C15 -1.3(9) . . . . ? Zn1 N1 C14 C15 179.2(5) . . . . ? N2 C15 C14 N1 1.0(10) . . . . ? C6 C8 N3 C11 119.8(4) . . . . ? C6 C8 N3 C9 -58.7(6) . . . . ? C9 N3 C11 N4 -0.5(5) . . . . ? C8 N3 C11 N4 -179.2(4) . . . . ? C11 N3 C9 C10 0.6(5) . . . . ? C8 N3 C9 C10 179.3(4) . . . . ? N3 C11 N4 C10 0.2(5) . . . . ? N3 C11 N4 Zn1 177.9(3) . . . 5 ? N3 C9 C10 N4 -0.4(6) . . . . ? C11 N4 C10 C9 0.2(5) . . . . ? Zn1 N4 C10 C9 -177.7(3) 5 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3W H3WA O1 0.85 1.87 2.718(5) 170.6 . O2W H2WA O2 0.84 1.87 2.687(4) 164.9 7_556 O1W H1WB O2W 0.84 1.92 2.713(5) 157.2 5_565 O1W H1WA O3W 0.84 1.88 2.691(5) 162.2 7 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.600 _refine_diff_density_min -1.138 _refine_diff_density_rms 0.129 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 857238' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H30 N8 O6 Cd, 3(H2 O)' _chemical_formula_sum 'C30 H36 Cd N8 O9' _chemical_formula_weight 765.07 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 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 25.876(8) _cell_length_b 9.8293(8) _cell_length_c 17.814(3) _cell_angle_alpha 90.00 _cell_angle_beta 133.12(3) _cell_angle_gamma 90.00 _cell_volume 3307(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296 _cell_measurement_reflns_used 2633 _cell_measurement_theta_min 3.1269 _cell_measurement_theta_max 29.0730 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.725 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8685 _exptl_absorpt_correction_T_max 0.8990 _exptl_absorpt_process_details SADABS(2009) _exptl_special_details ; ? ; _diffrn_ambient_temperature 296 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4200 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2863 _reflns_number_gt 2514 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of 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^)+(0.0543P)^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 2863 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.0000 0.09528(3) 0.2500 0.03419(13) Uani 1 2 d S . . N1 N 0.07909(11) 0.2598(3) 0.29093(17) 0.0381(6) Uani 1 1 d . . . N2 N 0.12440(11) 0.4462(3) 0.28764(17) 0.0337(5) Uani 1 1 d . . . N3 N 0.39401(12) 0.5122(3) 0.42721(17) 0.0435(6) Uani 1 1 d . . . N4 N 0.44375(13) 0.4288(3) 0.57860(18) 0.0444(6) Uani 1 1 d . . . O1 O 0.17520(11) 0.3613(3) -0.01353(16) 0.0502(6) Uani 1 1 d . . . O2 O 0.07172(11) 0.4255(3) -0.07022(16) 0.0566(7) Uani 1 1 d . . . O1W O -0.07372(12) -0.07484(18) 0.23019(18) 0.0495(6) Uani 1 1 d . . . H1WA H -0.0516 -0.1377 0.2411 0.074 Uiso 1 1 d R . . H1WB H -0.1131 -0.0753 0.1763 0.074 Uiso 1 1 d R . . O2W O 0.00000(12) 0.70570(18) 0.25000(18) 0.0416(7) Uani 1 2 d SR . . H2WA H 0.0164 0.6520 0.2988 0.062 Uiso 1 1 d R . . O3W O 0.29998(12) 0.3989(2) 0.03711(18) 0.0552(6) Uani 1 1 d . . . H3WB H 0.2610 0.3875 0.0214 0.066 Uiso 1 1 d R . . H3WA H 0.3071 0.3321 0.0148 0.083 Uiso 1 1 d R . . C1 C 0.15126(15) 0.2532(3) 0.3665(2) 0.0460(8) Uani 1 1 d . . . H1 H 0.1768 0.1812 0.4122 0.055 Uiso 1 1 calc R . . C2 C 0.17990(16) 0.3658(3) 0.3650(2) 0.0474(8) Uani 1 1 d . . . H2 H 0.2279 0.3854 0.4079 0.057 Uiso 1 1 calc R . . C3 C 0.06554(15) 0.3779(3) 0.2457(2) 0.0368(7) Uani 1 1 d . . . H3 H 0.0201 0.4099 0.1909 0.044 Uiso 1 1 calc R . . C4 C 0.12926(17) 0.5791(3) 0.2558(2) 0.0375(7) Uani 1 1 d . . . H4A H 0.1533 0.6427 0.3125 0.045 Uiso 1 1 calc R . . H4B H 0.0821 0.6137 0.1992 0.045 Uiso 1 1 calc R . . C5 C 0.16935(15) 0.5671(3) 0.2226(2) 0.0334(6) Uani 1 1 d . . . C6 C 0.13640(14) 0.5114(3) 0.12692(19) 0.0334(6) Uani 1 1 d . . . H6 H 0.0884 0.4903 0.0812 0.040 Uiso 1 1 calc R . . C7 C 0.17414(13) 0.4870(3) 0.09895(19) 0.0319(6) Uani 1 1 d . . . C8 C 0.24605(14) 0.5190(3) 0.16795(19) 0.0361(7) Uani 1 1 d . . . H8 H 0.2720 0.5009 0.1505 0.043 Uiso 1 1 calc R . . C9 C 0.27911(15) 0.5773(3) 0.2620(2) 0.0360(7) Uani 1 1 d . . . C10 C 0.24022(16) 0.6014(3) 0.2883(2) 0.0380(7) Uani 1 1 d . . . H10 H 0.2623 0.6414 0.3514 0.046 Uiso 1 1 calc R . . C11 C 0.35807(16) 0.6053(3) 0.3400(2) 0.0455(8) Uani 1 1 d . . . H11A H 0.3766 0.5933 0.3080 0.055 Uiso 1 1 calc R . . H11B H 0.3668 0.6986 0.3638 0.055 Uiso 1 1 calc R . . C12 C 0.42339(16) 0.5389(4) 0.5230(2) 0.0446(7) Uani 1 1 d . . . H12 H 0.4288 0.6263 0.5476 0.054 Uiso 1 1 calc R . . C13 C 0.4253(2) 0.3257(5) 0.5148(3) 0.0935(12) Uani 1 1 d . . . H13 H 0.4328 0.2340 0.5325 0.112 Uiso 1 1 calc R . . C14 C 0.3943(3) 0.3745(4) 0.4216(3) 0.0935(12) Uani 1 1 d . . . H14 H 0.3765 0.3235 0.3641 0.112 Uiso 1 1 calc R . . C15 C 0.13745(15) 0.4201(3) -0.0034(2) 0.0361(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 Cd1 0.03504(19) 0.03054(19) 0.0372(2) 0.000 0.02475(16) 0.000 N1 0.0360(12) 0.0340(14) 0.0441(13) 0.0024(11) 0.0274(11) -0.0014(11) N2 0.0360(13) 0.0344(13) 0.0359(12) -0.0007(10) 0.0266(12) -0.0015(11) N3 0.0410(13) 0.0487(17) 0.0311(12) -0.0074(12) 0.0209(12) -0.0051(13) N4 0.0439(15) 0.0422(16) 0.0361(14) -0.0012(11) 0.0231(13) -0.0011(12) O1 0.0447(11) 0.0623(15) 0.0484(13) -0.0158(11) 0.0337(11) 0.0000(11) O2 0.0339(12) 0.086(2) 0.0340(11) -0.0153(11) 0.0170(10) 0.0054(11) O1W 0.0465(12) 0.0449(14) 0.0538(13) -0.0040(10) 0.0330(12) -0.0050(10) O2W 0.0411(14) 0.0363(17) 0.0324(14) 0.000 0.0192(13) 0.000 O3W 0.0430(12) 0.0589(17) 0.0609(15) -0.0077(11) 0.0345(12) -0.0022(10) C1 0.0451(16) 0.0389(19) 0.0453(17) 0.0096(14) 0.0275(15) 0.0029(15) C2 0.0327(15) 0.0489(19) 0.0441(18) 0.0072(15) 0.0198(15) -0.0047(15) C3 0.0324(14) 0.0397(17) 0.0397(16) 0.0012(13) 0.0252(14) 0.0035(13) C4 0.0505(17) 0.0331(17) 0.0434(16) -0.0007(12) 0.0377(15) 0.0000(13) C5 0.0421(15) 0.0306(16) 0.0348(14) 0.0018(11) 0.0291(14) 0.0005(12) C6 0.0340(14) 0.0302(16) 0.0339(14) 0.0028(12) 0.0224(13) 0.0016(13) C7 0.0353(14) 0.0305(15) 0.0307(13) 0.0023(12) 0.0229(12) 0.0026(12) C8 0.0361(14) 0.0435(18) 0.0332(14) 0.0018(13) 0.0255(13) -0.0011(14) C9 0.0387(15) 0.0378(17) 0.0315(14) 0.0006(12) 0.0239(13) -0.0041(13) C10 0.0449(16) 0.0394(18) 0.0308(14) -0.0044(12) 0.0263(14) -0.0075(13) C11 0.0415(17) 0.056(2) 0.0358(16) -0.0016(14) 0.0252(15) -0.0090(15) C12 0.0515(18) 0.0430(19) 0.0362(16) -0.0091(14) 0.0288(15) -0.0078(16) C13 0.124(3) 0.0496(18) 0.0430(14) -0.0058(13) 0.0325(17) 0.0210(19) C14 0.124(3) 0.0496(18) 0.0430(14) -0.0058(13) 0.0325(17) 0.0210(19) C15 0.0397(16) 0.0375(17) 0.0311(15) -0.0003(12) 0.0242(14) 0.0003(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 Cd1 N1 2.301(2) . ? Cd1 N1 2.301(2) 2 ? Cd1 N4 2.328(3) 8_455 ? Cd1 N4 2.328(3) 7_556 ? Cd1 O1W 2.375(2) 2 ? Cd1 O1W 2.375(2) . ? N1 C3 1.316(4) . ? N1 C1 1.366(4) . ? N2 C3 1.332(4) . ? N2 C2 1.371(4) . ? N2 C4 1.464(4) . ? N3 C12 1.336(4) . ? N3 C14 1.358(5) . ? N3 C11 1.464(4) . ? N4 C12 1.311(4) . ? N4 C13 1.344(5) . ? N4 Cd1 2.328(3) 7_556 ? O1 C15 1.249(4) . ? O2 C15 1.243(4) . ? O1W H1WA 0.7717 . ? O1W H1WB 0.7886 . ? O2W H2WA 0.8424 . ? O3W H3WB 0.8501 . ? O3W H3WA 0.8498 . ? C1 C2 1.342(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.509(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C10 1.383(4) . ? C5 C6 1.395(4) . ? C6 C7 1.387(4) . ? C6 H6 0.9300 . ? C7 C8 1.395(4) . ? C7 C15 1.514(4) . ? C8 C9 1.382(4) . ? C8 H8 0.9300 . ? C9 C10 1.390(4) . ? C9 C11 1.516(4) . ? C10 H10 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12 0.9300 . ? C13 C14 1.345(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 N1 90.69(12) . 2 ? N1 Cd1 N4 96.33(9) . 8_455 ? N1 Cd1 N4 91.86(9) 2 8_455 ? N1 Cd1 N4 91.86(9) . 7_556 ? N1 Cd1 N4 96.33(9) 2 7_556 ? N4 Cd1 N4 168.35(13) 8_455 7_556 ? N1 Cd1 O1W 89.87(9) . 2 ? N1 Cd1 O1W 172.77(7) 2 2 ? N4 Cd1 O1W 80.91(9) 8_455 2 ? N4 Cd1 O1W 90.86(9) 7_556 2 ? N1 Cd1 O1W 172.77(7) . . ? N1 Cd1 O1W 89.87(9) 2 . ? N4 Cd1 O1W 90.86(9) 8_455 . ? N4 Cd1 O1W 80.91(9) 7_556 . ? O1W Cd1 O1W 90.48(10) 2 . ? C3 N1 C1 104.9(2) . . ? C3 N1 Cd1 128.21(19) . . ? C1 N1 Cd1 126.8(2) . . ? C3 N2 C2 106.5(3) . . ? C3 N2 C4 126.9(2) . . ? C2 N2 C4 126.6(2) . . ? C12 N3 C14 105.2(3) . . ? C12 N3 C11 128.9(3) . . ? C14 N3 C11 125.2(3) . . ? C12 N4 C13 104.9(3) . . ? C12 N4 Cd1 130.0(2) . 7_556 ? C13 N4 Cd1 125.1(3) . 7_556 ? Cd1 O1W H1WA 98.3 . . ? Cd1 O1W H1WB 115.0 . . ? H1WA O1W H1WB 114.9 . . ? H3WB O3W H3WA 109.5 . . ? C2 C1 N1 110.0(3) . . ? C2 C1 H1 125.0 . . ? N1 C1 H1 125.0 . . ? C1 C2 N2 106.4(3) . . ? C1 C2 H2 126.8 . . ? N2 C2 H2 126.8 . . ? N1 C3 N2 112.2(3) . . ? N1 C3 H3 123.9 . . ? N2 C3 H3 123.9 . . ? N2 C4 C5 110.3(2) . . ? N2 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C10 C5 C6 118.6(3) . . ? C10 C5 C4 121.3(3) . . ? C6 C5 C4 120.0(3) . . ? C7 C6 C5 121.0(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 119.1(2) . . ? C6 C7 C15 119.5(2) . . ? C8 C7 C15 121.3(2) . . ? C9 C8 C7 120.6(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 119.2(3) . . ? C8 C9 C11 121.0(3) . . ? C10 C9 C11 119.6(3) . . ? C5 C10 C9 121.3(3) . . ? C5 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? N3 C11 C9 109.8(2) . . ? N3 C11 H11A 109.7 . . ? C9 C11 H11A 109.7 . . ? N3 C11 H11B 109.7 . . ? C9 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N4 C12 N3 112.8(3) . . ? N4 C12 H12 123.6 . . ? N3 C12 H12 123.6 . . ? N4 C13 C14 110.0(4) . . ? N4 C13 H13 125.0 . . ? C14 C13 H13 125.0 . . ? C13 C14 N3 107.0(3) . . ? C13 C14 H14 126.5 . . ? N3 C14 H14 126.5 . . ? O2 C15 O1 125.1(3) . . ? O2 C15 C7 117.1(3) . . ? O1 C15 C7 117.8(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 N1 Cd1 N1 C3 -36.9(2) 2 . . . ? N4 Cd1 N1 C3 55.1(3) 8_455 . . . ? N4 Cd1 N1 C3 -133.2(3) 7_556 . . . ? O1W Cd1 N1 C3 135.9(2) 2 . . . ? N1 Cd1 N1 C1 145.4(3) 2 . . . ? N4 Cd1 N1 C1 -122.6(2) 8_455 . . . ? N4 Cd1 N1 C1 49.1(2) 7_556 . . . ? O1W Cd1 N1 C1 -41.8(2) 2 . . . ? C3 N1 C1 C2 -0.6(4) . . . . ? Cd1 N1 C1 C2 177.5(2) . . . . ? N1 C1 C2 N2 0.9(4) . . . . ? C3 N2 C2 C1 -0.8(3) . . . . ? C4 N2 C2 C1 -179.2(3) . . . . ? C1 N1 C3 N2 0.1(3) . . . . ? Cd1 N1 C3 N2 -177.97(17) . . . . ? C2 N2 C3 N1 0.4(3) . . . . ? C4 N2 C3 N1 178.8(2) . . . . ? C3 N2 C4 C5 -118.9(3) . . . . ? C2 N2 C4 C5 59.2(4) . . . . ? N2 C4 C5 C10 -99.0(3) . . . . ? N2 C4 C5 C6 76.3(3) . . . . ? C10 C5 C6 C7 1.8(4) . . . . ? C4 C5 C6 C7 -173.6(3) . . . . ? C5 C6 C7 C8 0.0(4) . . . . ? C5 C6 C7 C15 177.1(3) . . . . ? C6 C7 C8 C9 -1.5(4) . . . . ? C15 C7 C8 C9 -178.6(3) . . . . ? C7 C8 C9 C10 1.3(4) . . . . ? C7 C8 C9 C11 176.6(3) . . . . ? C6 C5 C10 C9 -2.1(4) . . . . ? C4 C5 C10 C9 173.3(3) . . . . ? C8 C9 C10 C5 0.5(4) . . . . ? C11 C9 C10 C5 -174.8(3) . . . . ? C12 N3 C11 C9 -108.0(3) . . . . ? C14 N3 C11 C9 61.0(5) . . . . ? C8 C9 C11 N3 -109.6(3) . . . . ? C10 C9 C11 N3 65.6(4) . . . . ? C13 N4 C12 N3 -1.2(4) . . . . ? Cd1 N4 C12 N3 178.59(19) 7_556 . . . ? C14 N3 C12 N4 1.7(4) . . . . ? C11 N3 C12 N4 172.4(3) . . . . ? C12 N4 C13 C14 0.3(6) . . . . ? Cd1 N4 C13 C14 -179.6(3) 7_556 . . . ? N4 C13 C14 N3 0.7(6) . . . . ? C12 N3 C14 C13 -1.4(5) . . . . ? C11 N3 C14 C13 -172.6(4) . . . . ? C6 C7 C15 O2 20.4(4) . . . . ? C8 C7 C15 O2 -162.5(3) . . . . ? C6 C7 C15 O1 -158.0(3) . . . . ? C8 C7 C15 O1 19.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O2W 0.77 1.97 2.738(2) 172.1 1_545 O1W H1WB O3W 0.79 1.91 2.685(4) 167.5 3_445 O2W H2WA O2 0.84 1.87 2.691(3) 163.2 6_566 O3W H3WB O1 0.85 1.87 2.719(3) 179.6 . O3W H3WA O1 0.85 1.96 2.738(3) 151.8 7 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.750 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.067 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 857239' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 Cl2 N8 O7 Zn2' _chemical_formula_weight 818.28 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' Cl Cl 0.1484 0.1585 '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 12.5528(6) _cell_length_b 10.2544(4) _cell_length_c 15.8665(11) _cell_angle_alpha 90.00 _cell_angle_beta 120.961(4) _cell_angle_gamma 90.00 _cell_volume 1751.36(16) _cell_formula_units_Z 2 _cell_measurement_temperature 296 _cell_measurement_reflns_used 3697 _cell_measurement_theta_min 2.9500 _cell_measurement_theta_max 29.0329 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 1.579 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7430 _exptl_absorpt_correction_T_max 0.7863 _exptl_absorpt_process_details SADABS(2009) _exptl_special_details ; ? ; _diffrn_ambient_temperature 296 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7186 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3069 _reflns_number_gt 2594 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of 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^)+(0.0329P)^2^+1.8801P] 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 3069 _refine_ls_number_parameters 226 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0880 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C7 C 0.6302(3) 0.2402(3) 0.9648(2) 0.0346(7) Uani 1 1 d . . . N3 N 0.6112(2) -0.2655(2) 0.86423(17) 0.0332(6) Uani 1 1 d . . . Zn1 Zn -0.26295(3) 0.04771(3) 0.58106(2) 0.03316(13) Uani 1 1 d . . . Cl1 Cl -0.29716(8) -0.02579(9) 0.70166(7) 0.0521(2) Uani 1 1 d . . . O1 O 0.6106(2) 0.3183(2) 1.01744(16) 0.0456(6) Uani 1 1 d . . . C6 C 0.5602(3) 0.0305(3) 0.87018(19) 0.0298(6) Uani 1 1 d . . . H6 H 0.6334 0.0302 0.8689 0.036 Uiso 1 1 calc R . . C2 C 0.4242(3) 0.1346(3) 0.9136(2) 0.0314(7) Uani 1 1 d . . . H2 H 0.4069 0.2038 0.9425 0.038 Uiso 1 1 calc R . . O2 O 0.7213(2) 0.2475(3) 0.95557(19) 0.0594(7) Uani 1 1 d . . . N4 N 0.7082(2) -0.4066(2) 0.98375(19) 0.0374(6) Uani 1 1 d . . . N1 N -0.0809(2) 0.0866(3) 0.65797(19) 0.0404(6) Uani 1 1 d . . . N2 N 0.1124(2) 0.0734(2) 0.77961(18) 0.0359(6) Uani 1 1 d . . . C3 C 0.3393(3) 0.0344(3) 0.8705(2) 0.0311(7) Uani 1 1 d . . . C4 C 0.3670(3) -0.0693(3) 0.8280(2) 0.0332(7) Uani 1 1 d . . . H4 H 0.3106 -0.1374 0.7992 0.040 Uiso 1 1 calc R . . C5 C 0.4771(3) -0.0724(3) 0.82792(19) 0.0296(6) Uani 1 1 d . . . C11 C -0.0014(3) 0.0278(3) 0.7409(3) 0.0464(9) Uani 1 1 d . . . H11 H -0.0233 -0.0386 0.7690 0.056 Uiso 1 1 calc R . . C1 C 0.5356(3) 0.1331(3) 0.91414(19) 0.0288(6) Uani 1 1 d . . . C8 C 0.2212(3) 0.0348(4) 0.8737(2) 0.0434(8) Uani 1 1 d . . . H8A H 0.2075 -0.0518 0.8910 0.052 Uiso 1 1 calc R . . H8B H 0.2306 0.0945 0.9246 0.052 Uiso 1 1 calc R . . C15 C 0.5993(3) -0.3648(3) 0.9134(2) 0.0356(7) Uani 1 1 d . . . H15 H 0.5236 -0.3998 0.8996 0.043 Uiso 1 1 calc R . . C13 C 0.7361(3) -0.2409(4) 0.9072(3) 0.0507(9) Uani 1 1 d . . . H13 H 0.7730 -0.1763 0.8896 0.061 Uiso 1 1 calc R . . C12 C 0.5091(3) -0.1889(3) 0.7864(2) 0.0366(7) Uani 1 1 d . . . H12A H 0.4363 -0.2439 0.7508 0.044 Uiso 1 1 calc R . . H12B H 0.5327 -0.1589 0.7403 0.044 Uiso 1 1 calc R . . C14 C 0.7947(3) -0.3292(3) 0.9803(3) 0.0518(9) Uani 1 1 d . . . H14 H 0.8803 -0.3362 1.0218 0.062 Uiso 1 1 calc R . . C9 C 0.1065(4) 0.1717(5) 0.7203(3) 0.0787(15) Uani 1 1 d . . . H9 H 0.1717 0.2249 0.7298 0.094 Uiso 1 1 calc R . . C10 C -0.0122(3) 0.1777(4) 0.6450(3) 0.0705(13) Uani 1 1 d . . . H10 H -0.0423 0.2353 0.5923 0.085 Uiso 1 1 calc R . . O1W O 0.1258(5) 0.8068(6) 0.1233(4) 0.171(2) Uani 1 1 d . . . H1WA H 0.1845 0.8547 0.1652 0.257 Uiso 1 1 d R . . H1WB H 0.1885 0.7884 0.1186 0.257 Uiso 1 1 d R . . O2W O 0.9765(14) 0.4784(16) 0.5370(11) 0.236(7) Uani 0.50 1 d PU . . H2WB H 0.9384 0.4327 0.4850 0.354 Uiso 0.50 1 d PR . . H2WA H 0.9609 0.5586 0.5225 0.354 Uiso 0.50 1 d PR . . 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 C7 0.0337(18) 0.0319(16) 0.0263(15) 0.0026(13) 0.0069(14) -0.0012(14) N3 0.0391(15) 0.0282(13) 0.0347(13) -0.0013(10) 0.0206(12) 0.0022(11) Zn1 0.0283(2) 0.0318(2) 0.0332(2) 0.00130(14) 0.01134(16) 0.00068(15) Cl1 0.0477(5) 0.0650(6) 0.0493(5) 0.0194(4) 0.0290(4) 0.0083(4) O1 0.0502(14) 0.0368(12) 0.0471(13) -0.0152(10) 0.0231(12) -0.0106(11) C6 0.0284(16) 0.0319(16) 0.0251(14) 0.0020(12) 0.0109(13) 0.0017(13) C2 0.0317(16) 0.0315(16) 0.0238(14) 0.0014(12) 0.0091(13) 0.0070(13) O2 0.0429(15) 0.0678(17) 0.0691(17) -0.0289(14) 0.0300(14) -0.0221(13) N4 0.0342(15) 0.0347(14) 0.0444(15) 0.0020(12) 0.0209(13) 0.0002(12) N1 0.0256(14) 0.0471(16) 0.0392(15) 0.0065(12) 0.0100(12) -0.0022(12) N2 0.0256(14) 0.0422(15) 0.0331(13) 0.0060(11) 0.0102(12) -0.0013(11) C3 0.0252(15) 0.0380(17) 0.0223(14) 0.0050(12) 0.0068(13) 0.0026(13) C4 0.0320(17) 0.0327(16) 0.0235(14) -0.0006(12) 0.0062(13) -0.0056(13) C5 0.0340(17) 0.0297(15) 0.0185(13) 0.0021(11) 0.0089(13) 0.0041(13) C11 0.0292(18) 0.053(2) 0.0465(19) 0.0146(16) 0.0121(16) -0.0062(16) C1 0.0296(16) 0.0286(15) 0.0206(13) 0.0030(11) 0.0075(12) 0.0003(13) C8 0.0312(17) 0.062(2) 0.0293(16) 0.0052(15) 0.0103(14) 0.0023(16) C15 0.0360(18) 0.0318(16) 0.0377(17) -0.0031(13) 0.0180(15) -0.0030(14) C13 0.049(2) 0.049(2) 0.067(2) 0.0128(18) 0.040(2) 0.0013(17) C12 0.0456(19) 0.0320(16) 0.0284(15) -0.0038(12) 0.0162(15) 0.0014(14) C14 0.0343(19) 0.055(2) 0.066(2) 0.0131(19) 0.0261(18) 0.0035(17) C9 0.037(2) 0.093(3) 0.080(3) 0.042(3) 0.012(2) -0.018(2) C10 0.038(2) 0.088(3) 0.066(3) 0.041(2) 0.013(2) -0.004(2) O1W 0.126(4) 0.240(6) 0.158(4) -0.059(4) 0.081(4) -0.002(4) O2W 0.237(7) 0.237(7) 0.235(7) 0.001(2) 0.123(4) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C7 O2 1.228(4) . ? C7 O1 1.269(4) . ? C7 C1 1.510(4) . ? N3 C15 1.337(4) . ? N3 C13 1.373(4) . ? N3 C12 1.469(4) . ? Zn1 O1 1.944(2) 4_465 ? Zn1 N1 2.001(3) . ? Zn1 N4 2.008(3) 4_455 ? Zn1 Cl1 2.2933(9) . ? O1 Zn1 1.944(2) 4_666 ? C6 C1 1.383(4) . ? C6 C5 1.389(4) . ? C6 H6 0.9300 . ? C2 C3 1.382(4) . ? C2 C1 1.393(4) . ? C2 H2 0.9300 . ? N4 C15 1.315(4) . ? N4 C14 1.369(4) . ? N4 Zn1 2.008(3) 4_656 ? N1 C11 1.319(4) . ? N1 C10 1.356(4) . ? N2 C11 1.317(4) . ? N2 C9 1.354(4) . ? N2 C8 1.468(4) . ? C3 C4 1.396(4) . ? C3 C8 1.510(4) . ? C4 C5 1.382(4) . ? C4 H4 0.9300 . ? C5 C12 1.515(4) . ? C11 H11 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C15 H15 0.9300 . ? C13 C14 1.352(5) . ? C13 H13 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 H14 0.9300 . ? C9 C10 1.349(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8499 . ? O2W O2W 1.63(2) 3_766 ? O2W H2WB 0.8500 . ? O2W H2WA 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C7 O1 123.2(3) . . ? O2 C7 C1 120.5(3) . . ? O1 C7 C1 116.3(3) . . ? C15 N3 C13 107.0(3) . . ? C15 N3 C12 125.9(3) . . ? C13 N3 C12 126.8(3) . . ? O1 Zn1 N1 123.18(10) 4_465 . ? O1 Zn1 N4 109.51(10) 4_465 4_455 ? N1 Zn1 N4 108.07(11) . 4_455 ? O1 Zn1 Cl1 102.25(7) 4_465 . ? N1 Zn1 Cl1 101.67(8) . . ? N4 Zn1 Cl1 111.57(8) 4_455 . ? C7 O1 Zn1 113.9(2) . 4_666 ? C1 C6 C5 121.0(3) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C15 N4 C14 106.1(3) . . ? C15 N4 Zn1 125.8(2) . 4_656 ? C14 N4 Zn1 128.0(2) . 4_656 ? C11 N1 C10 104.6(3) . . ? C11 N1 Zn1 123.9(2) . . ? C10 N1 Zn1 131.3(2) . . ? C11 N2 C9 106.4(3) . . ? C11 N2 C8 126.6(3) . . ? C9 N2 C8 126.7(3) . . ? C2 C3 C4 119.0(3) . . ? C2 C3 C8 120.2(3) . . ? C4 C3 C8 120.8(3) . . ? C5 C4 C3 121.0(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 119.0(3) . . ? C4 C5 C12 120.5(3) . . ? C6 C5 C12 120.5(3) . . ? N2 C11 N1 112.6(3) . . ? N2 C11 H11 123.7 . . ? N1 C11 H11 123.7 . . ? C6 C1 C2 119.3(3) . . ? C6 C1 C7 120.2(3) . . ? C2 C1 C7 120.5(3) . . ? N2 C8 C3 112.4(3) . . ? N2 C8 H8A 109.1 . . ? C3 C8 H8A 109.1 . . ? N2 C8 H8B 109.1 . . ? C3 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? N4 C15 N3 111.4(3) . . ? N4 C15 H15 124.3 . . ? N3 C15 H15 124.3 . . ? C14 C13 N3 106.4(3) . . ? C14 C13 H13 126.8 . . ? N3 C13 H13 126.8 . . ? N3 C12 C5 111.6(2) . . ? N3 C12 H12A 109.3 . . ? C5 C12 H12A 109.3 . . ? N3 C12 H12B 109.3 . . ? C5 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C13 C14 N4 109.2(3) . . ? C13 C14 H14 125.4 . . ? N4 C14 H14 125.4 . . ? C10 C9 N2 106.9(3) . . ? C10 C9 H9 126.6 . . ? N2 C9 H9 126.6 . . ? C9 C10 N1 109.4(3) . . ? C9 C10 H10 125.3 . . ? N1 C10 H10 125.3 . . ? H1WA O1W H1WB 74.1 . . ? O2W O2W H2WB 71.4 3_766 . ? O2W O2W H2WA 70.0 3_766 . ? H2WB O2W H2WA 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C7 O1 Zn1 0.8(4) . . . 4_666 ? C1 C7 O1 Zn1 179.48(18) . . . 4_666 ? O1 Zn1 N1 C11 140.0(3) 4_465 . . . ? N4 Zn1 N1 C11 -90.7(3) 4_455 . . . ? Cl1 Zn1 N1 C11 26.8(3) . . . . ? O1 Zn1 N1 C10 -35.1(4) 4_465 . . . ? N4 Zn1 N1 C10 94.2(4) 4_455 . . . ? Cl1 Zn1 N1 C10 -148.3(4) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C1 C2 C3 C8 177.7(3) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C8 C3 C4 C5 -177.6(3) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C3 C4 C5 C12 176.8(2) . . . . ? C1 C6 C5 C4 1.7(4) . . . . ? C1 C6 C5 C12 -175.7(2) . . . . ? C9 N2 C11 N1 2.4(5) . . . . ? C8 N2 C11 N1 176.5(3) . . . . ? C10 N1 C11 N2 -1.4(4) . . . . ? Zn1 N1 C11 N2 -177.7(2) . . . . ? C5 C6 C1 C2 -1.7(4) . . . . ? C5 C6 C1 C7 176.5(2) . . . . ? C3 C2 C1 C6 0.6(4) . . . . ? C3 C2 C1 C7 -177.6(2) . . . . ? O2 C7 C1 C6 10.5(4) . . . . ? O1 C7 C1 C6 -168.3(3) . . . . ? O2 C7 C1 C2 -171.4(3) . . . . ? O1 C7 C1 C2 9.9(4) . . . . ? C11 N2 C8 C3 144.5(3) . . . . ? C9 N2 C8 C3 -42.5(5) . . . . ? C2 C3 C8 N2 103.6(3) . . . . ? C4 C3 C8 N2 -79.2(4) . . . . ? C14 N4 C15 N3 0.7(4) . . . . ? Zn1 N4 C15 N3 176.80(19) 4_656 . . . ? C13 N3 C15 N4 -1.1(3) . . . . ? C12 N3 C15 N4 -175.0(3) . . . . ? C15 N3 C13 C14 1.0(4) . . . . ? C12 N3 C13 C14 174.9(3) . . . . ? C15 N3 C12 C5 89.7(3) . . . . ? C13 N3 C12 C5 -83.0(4) . . . . ? C4 C5 C12 N3 -109.3(3) . . . . ? C6 C5 C12 N3 68.0(3) . . . . ? N3 C13 C14 N4 -0.7(4) . . . . ? C15 N4 C14 C13 0.0(4) . . . . ? Zn1 N4 C14 C13 -176.0(2) 4_656 . . . ? C11 N2 C9 C10 -2.3(5) . . . . ? C8 N2 C9 C10 -176.4(4) . . . . ? N2 C9 C10 N1 1.6(6) . . . . ? C11 N1 C10 C9 -0.2(5) . . . . ? Zn1 N1 C10 C9 175.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA Cl1 0.85 2.54 3.352(5) 159.4 3_566 O1W H1WB O2 0.85 2.04 2.834(5) 154.7 3_666 O2W H2WB O1W 0.85 1.96 2.802(17) 170.2 2_645 O2W H2WA O1W 0.85 2.31 2.757(17) 113.0 4_676 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.421 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.062 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 857240' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 Cd Cl N4 O2' _chemical_formula_sum 'C15 H13 Cd Cl N4 O2' _chemical_formula_weight 429.14 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' Cl Cl 0.1484 0.1585 '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 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 8.8844(4) _cell_length_b 10.4799(5) _cell_length_c 17.2726(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.368(4) _cell_angle_gamma 90.00 _cell_volume 1591.09(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3191 _cell_measurement_theta_min 3.0184 _cell_measurement_theta_max 28.9528 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.554 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7463 _exptl_absorpt_correction_T_max 0.7891 _exptl_absorpt_process_details SADABS(2009) _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7543 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2802 _reflns_number_gt 2001 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of 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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2802 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 2.137 _refine_ls_restrained_S_all 2.137 _refine_ls_shift/su_max 0.087 _refine_ls_shift/su_mean 0.008 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 C12 C 1.0738(6) 0.7498(7) -0.0968(4) 0.064(2) Uani 1 1 d . . . H12A H 1.0707 0.8215 -0.1325 0.077 Uiso 1 1 calc R . . H12B H 1.1757 0.7144 -0.0911 0.077 Uiso 1 1 calc R . . Cd1 Cd 1.5000 1.06811(6) 0.2500 0.0442(2) Uani 1 2 d S . . Cd2 Cd 1.5000 1.43880(6) 0.2500 0.0392(2) Uani 1 2 d S . . Cl1 Cl 1.54911(16) 1.24125(17) 0.15355(8) 0.0476(4) Uani 1 1 d . . . N4 N 0.7538(5) 0.5691(5) -0.1918(3) 0.0495(15) Uani 1 1 d . . . N3 N 0.9671(6) 0.6532(6) -0.1317(3) 0.0496(15) Uani 1 1 d . . . C4 C 0.8976(7) 0.8111(6) -0.0012(4) 0.0503(18) Uani 1 1 d . . . H4 H 0.8160 0.7847 -0.0376 0.060 Uiso 1 1 calc R . . C13 C 0.8353(7) 0.6729(7) -0.1793(4) 0.0509(18) Uani 1 1 d . . . H13 H 0.8054 0.7518 -0.2009 0.061 Uiso 1 1 calc R . . C3 C 1.0453(6) 0.7980(6) -0.0193(4) 0.0462(18) Uani 1 1 d . . . C5 C 0.8690(7) 0.8621(6) 0.0689(4) 0.0435(17) Uani 1 1 d . . . C1 C 1.1390(7) 0.8916(6) 0.1064(4) 0.0489(19) Uani 1 1 d . . . C7 C 1.2662(7) 0.9489(7) 0.1631(5) 0.059(2) Uani 1 1 d . . . O2 O 1.4008(4) 0.9309(4) 0.1483(2) 0.0442(2) Uani 1 1 d . . . C2 C 1.1640(6) 0.8399(6) 0.0362(4) 0.0489(19) Uani 1 1 d . . . H2 H 1.2633 0.8328 0.0255 0.059 Uiso 1 1 calc R . . C6 C 0.9932(8) 0.9018(6) 0.1233(4) 0.0494(18) Uani 1 1 d . . . H6 H 0.9766 0.9352 0.1712 0.059 Uiso 1 1 calc R . . O1 O 1.2399(5) 1.0100(5) 0.2203(3) 0.0675(15) Uani 1 1 d . . . C14 C 0.9688(8) 0.5260(8) -0.1123(4) 0.072(2) Uani 1 1 d . . . H14 H 1.0448 0.4831 -0.0797 0.086 Uiso 1 1 calc R . . C15 C 0.8387(8) 0.4759(7) -0.1499(4) 0.073(3) Uani 1 1 d . . . H15 H 0.8105 0.3906 -0.1478 0.088 Uiso 1 1 calc R . . N1 N 0.6392(5) 0.7540(6) 0.1016(3) 0.0457(13) Uani 1 1 d . . . C8 C 0.7080(7) 0.8753(6) 0.0872(4) 0.0517(19) Uani 1 1 d . . . H8A H 0.7090 0.9291 0.1330 0.062 Uiso 1 1 calc R . . H8B H 0.6461 0.9172 0.0437 0.062 Uiso 1 1 calc R . . C11 C 0.5629(10) 0.6765(8) 0.0466(4) 0.099(3) Uani 1 1 d . . . H11 H 0.5470 0.6900 -0.0072 0.118 Uiso 1 1 calc R . . N2 N 0.5549(6) 0.5904(5) 0.1616(3) 0.0531(16) Uani 1 1 d . . . C9 C 0.6270(7) 0.6995(7) 0.1696(4) 0.0483(18) Uani 1 1 d . . . H9 H 0.6656 0.7349 0.2178 0.058 Uiso 1 1 calc R . . C10 C 0.5143(10) 0.5759(8) 0.0851(4) 0.103(3) Uani 1 1 d . . . H10 H 0.4604 0.5067 0.0614 0.123 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C12 0.035(4) 0.087(6) 0.072(5) -0.011(5) 0.012(3) -0.017(5) Cd1 0.0323(4) 0.0443(5) 0.0522(5) 0.000 -0.0067(3) 0.000 Cd2 0.0374(4) 0.0448(5) 0.0345(4) 0.000 0.0023(3) 0.000 Cl1 0.0509(9) 0.0573(11) 0.0370(8) 0.0038(10) 0.0147(6) 0.0096(10) N4 0.034(3) 0.048(4) 0.063(4) -0.003(3) -0.004(3) 0.000(3) N3 0.034(3) 0.061(4) 0.054(4) -0.009(3) 0.005(3) -0.002(3) C4 0.039(4) 0.057(5) 0.052(4) -0.006(4) -0.003(3) -0.010(4) C13 0.042(4) 0.058(5) 0.054(5) 0.007(4) 0.010(3) 0.007(4) C3 0.031(4) 0.053(5) 0.054(4) -0.006(4) 0.002(3) -0.007(3) C5 0.041(4) 0.036(4) 0.052(4) 0.005(3) 0.001(3) -0.007(3) C1 0.030(4) 0.043(4) 0.068(5) 0.004(4) -0.011(3) -0.012(3) C7 0.035(4) 0.051(5) 0.082(6) -0.003(5) -0.017(4) 0.002(4) O2 0.0323(4) 0.0443(5) 0.0522(5) 0.000 -0.0067(3) 0.000 C2 0.027(4) 0.047(4) 0.070(5) 0.009(4) -0.003(3) -0.003(3) C6 0.067(5) 0.037(4) 0.041(4) 0.005(3) -0.004(4) -0.014(4) O1 0.052(3) 0.080(4) 0.064(4) -0.011(3) -0.012(3) -0.022(3) C14 0.063(5) 0.069(6) 0.077(6) -0.002(5) -0.012(4) 0.018(5) C15 0.070(6) 0.048(5) 0.093(6) -0.004(5) -0.015(5) 0.010(5) N1 0.043(3) 0.052(3) 0.041(3) 0.001(4) 0.000(2) -0.010(3) C8 0.046(4) 0.047(5) 0.064(5) -0.003(4) 0.014(4) -0.006(4) C11 0.155(8) 0.106(7) 0.032(4) -0.005(5) 0.005(5) -0.066(7) N2 0.075(4) 0.052(4) 0.030(3) -0.002(3) -0.002(3) -0.014(3) C9 0.048(4) 0.064(5) 0.032(4) -0.009(4) 0.001(3) -0.003(4) C10 0.177(9) 0.086(7) 0.042(5) 0.003(5) 0.007(5) -0.068(7) _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 C12 N3 1.457(7) . ? C12 C3 1.486(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? Cd1 O2 2.341(4) . ? Cd1 O2 2.341(4) 2_855 ? Cd1 O1 2.372(4) . ? Cd1 O1 2.372(4) 2_855 ? Cd1 Cl1 2.5436(16) 2_855 ? Cd1 Cl1 2.5436(16) . ? Cd1 C7 2.687(6) . ? Cd1 C7 2.687(6) 2_855 ? Cd2 N2 2.304(5) 2_765 ? Cd2 N2 2.304(5) 1_665 ? Cd2 N4 2.333(4) 3_775 ? Cd2 N4 2.333(4) 4_676 ? Cd2 Cl1 2.7320(17) . ? Cd2 Cl1 2.7320(17) 2_855 ? N4 C13 1.307(7) . ? N4 C15 1.375(7) . ? N4 Cd2 2.333(4) 3_775 ? N3 C13 1.345(6) . ? N3 C14 1.374(8) . ? C4 C5 1.381(8) . ? C4 C3 1.400(8) . ? C4 H4 0.9300 . ? C13 H13 0.9300 . ? C3 C2 1.389(7) . ? C5 C6 1.404(7) . ? C5 C8 1.516(8) . ? C1 C2 1.376(8) . ? C1 C6 1.373(9) . ? C1 C7 1.508(8) . ? C7 O1 1.228(8) . ? C7 O2 1.273(7) . ? C2 H2 0.9300 . ? C6 H6 0.9300 . ? C14 C15 1.347(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N1 C9 1.325(7) . ? N1 C11 1.354(8) . ? N1 C8 1.447(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C11 C10 1.350(9) . ? C11 H11 0.9300 . ? N2 C9 1.307(7) . ? N2 C10 1.328(7) . ? N2 Cd2 2.304(5) 1_445 ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? 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 N3 C12 C3 115.0(5) . . ? N3 C12 H12A 108.5 . . ? C3 C12 H12A 108.5 . . ? N3 C12 H12B 108.5 . . ? C3 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? O2 Cd1 O2 104.22(18) . 2_855 ? O2 Cd1 O1 55.36(16) . . ? O2 Cd1 O1 104.67(15) 2_855 . ? O2 Cd1 O1 104.67(15) . 2_855 ? O2 Cd1 O1 55.36(16) 2_855 2_855 ? O1 Cd1 O1 150.3(3) . 2_855 ? O2 Cd1 Cl1 147.98(10) . 2_855 ? O2 Cd1 Cl1 91.62(10) 2_855 2_855 ? O1 Cd1 Cl1 94.01(13) . 2_855 ? O1 Cd1 Cl1 107.22(12) 2_855 2_855 ? O2 Cd1 Cl1 91.62(10) . . ? O2 Cd1 Cl1 147.98(10) 2_855 . ? O1 Cd1 Cl1 107.22(12) . . ? O1 Cd1 Cl1 94.01(14) 2_855 . ? Cl1 Cd1 Cl1 88.98(7) 2_855 . ? O2 Cd1 C7 28.27(18) . . ? O2 Cd1 C7 108.03(17) 2_855 . ? O1 Cd1 C7 27.19(18) . . ? O1 Cd1 C7 130.61(19) 2_855 . ? Cl1 Cd1 C7 120.34(18) 2_855 . ? Cl1 Cd1 C7 99.12(16) . . ? O2 Cd1 C7 108.03(17) . 2_855 ? O2 Cd1 C7 28.27(18) 2_855 2_855 ? O1 Cd1 C7 130.61(19) . 2_855 ? O1 Cd1 C7 27.19(18) 2_855 2_855 ? Cl1 Cd1 C7 99.12(16) 2_855 2_855 ? Cl1 Cd1 C7 120.34(18) . 2_855 ? C7 Cd1 C7 124.6(3) . 2_855 ? N2 Cd2 N2 92.8(3) 2_765 1_665 ? N2 Cd2 N4 91.47(18) 2_765 3_775 ? N2 Cd2 N4 91.34(19) 1_665 3_775 ? N2 Cd2 N4 91.34(19) 2_765 4_676 ? N2 Cd2 N4 91.47(18) 1_665 4_676 ? N4 Cd2 N4 175.9(3) 3_775 4_676 ? N2 Cd2 Cl1 174.02(14) 2_765 . ? N2 Cd2 Cl1 92.91(14) 1_665 . ? N4 Cd2 Cl1 86.58(13) 3_775 . ? N4 Cd2 Cl1 90.33(14) 4_676 . ? N2 Cd2 Cl1 92.91(14) 2_765 2_855 ? N2 Cd2 Cl1 174.02(14) 1_665 2_855 ? N4 Cd2 Cl1 90.33(14) 3_775 2_855 ? N4 Cd2 Cl1 86.58(13) 4_676 2_855 ? Cl1 Cd2 Cl1 81.46(7) . 2_855 ? Cd1 Cl1 Cd2 94.78(5) . . ? C13 N4 C15 104.8(5) . . ? C13 N4 Cd2 125.3(4) . 3_775 ? C15 N4 Cd2 128.6(5) . 3_775 ? C13 N3 C14 106.0(5) . . ? C13 N3 C12 127.1(6) . . ? C14 N3 C12 126.1(6) . . ? C5 C4 C3 122.2(6) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? N4 C13 N3 112.7(6) . . ? N4 C13 H13 123.7 . . ? N3 C13 H13 123.7 . . ? C4 C3 C2 117.2(6) . . ? C4 C3 C12 121.5(5) . . ? C2 C3 C12 121.1(6) . . ? C4 C5 C6 118.3(6) . . ? C4 C5 C8 121.2(5) . . ? C6 C5 C8 120.5(6) . . ? C2 C1 C6 119.8(5) . . ? C2 C1 C7 121.9(6) . . ? C6 C1 C7 118.1(7) . . ? O1 C7 O2 122.2(6) . . ? O1 C7 C1 121.2(7) . . ? O2 C7 C1 116.6(7) . . ? O1 C7 Cd1 62.0(3) . . ? O2 C7 Cd1 60.6(3) . . ? C1 C7 Cd1 173.2(5) . . ? C7 O2 Cd1 91.2(4) . . ? C1 C2 C3 121.9(6) . . ? C1 C2 H2 119.0 . . ? C3 C2 H2 119.0 . . ? C1 C6 C5 120.5(7) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C7 O1 Cd1 90.8(4) . . ? C15 C14 N3 106.5(6) . . ? C15 C14 H14 126.8 . . ? N3 C14 H14 126.8 . . ? C14 C15 N4 110.0(6) . . ? C14 C15 H15 125.0 . . ? N4 C15 H15 125.0 . . ? C9 N1 C11 105.4(6) . . ? C9 N1 C8 128.5(6) . . ? C11 N1 C8 126.0(6) . . ? N1 C8 C5 113.0(5) . . ? N1 C8 H8A 109.0 . . ? C5 C8 H8A 109.0 . . ? N1 C8 H8B 109.0 . . ? C5 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C11 N1 106.7(7) . . ? C10 C11 H11 126.7 . . ? N1 C11 H11 126.7 . . ? C9 N2 C10 105.2(6) . . ? C9 N2 Cd2 132.9(4) . 1_445 ? C10 N2 Cd2 121.8(5) . 1_445 ? N2 C9 N1 112.7(6) . . ? N2 C9 H9 123.6 . . ? N1 C9 H9 123.6 . . ? C11 C10 N2 109.9(7) . . ? C11 C10 H10 125.1 . . ? N2 C10 H10 125.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cd1 Cl1 Cd2 147.98(10) . . . . ? O2 Cd1 Cl1 Cd2 -91.4(2) 2_855 . . . ? O1 Cd1 Cl1 Cd2 93.89(14) . . . . ? O1 Cd1 Cl1 Cd2 -107.19(12) 2_855 . . . ? Cl1 Cd1 Cl1 Cd2 0.0 2_855 . . . ? C7 Cd1 Cl1 Cd2 120.58(18) . . . . ? C7 Cd1 Cl1 Cd2 -99.97(18) 2_855 . . . ? N2 Cd2 Cl1 Cd1 -19.8(12) 2_765 . . . ? N2 Cd2 Cl1 Cd1 177.98(13) 1_665 . . . ? N4 Cd2 Cl1 Cd1 -90.85(14) 3_775 . . . ? N4 Cd2 Cl1 Cd1 86.49(13) 4_676 . . . ? Cl1 Cd2 Cl1 Cd1 0.0 2_855 . . . ? C3 C12 N3 C13 89.7(8) . . . . ? C3 C12 N3 C14 -78.8(9) . . . . ? C15 N4 C13 N3 -0.3(8) . . . . ? Cd2 N4 C13 N3 167.9(4) 3_775 . . . ? C14 N3 C13 N4 -0.2(8) . . . . ? C12 N3 C13 N4 -170.5(6) . . . . ? C5 C4 C3 C2 -0.7(10) . . . . ? C5 C4 C3 C12 -176.5(6) . . . . ? N3 C12 C3 C4 -34.7(10) . . . . ? N3 C12 C3 C2 149.8(6) . . . . ? C3 C4 C5 C6 0.1(10) . . . . ? C3 C4 C5 C8 -179.9(6) . . . . ? C2 C1 C7 O1 169.9(7) . . . . ? C6 C1 C7 O1 -4.6(10) . . . . ? C2 C1 C7 O2 -9.8(10) . . . . ? C6 C1 C7 O2 175.8(6) . . . . ? C2 C1 C7 Cd1 54(5) . . . . ? C6 C1 C7 Cd1 -121(4) . . . . ? O2 Cd1 C7 O1 173.7(7) . . . . ? O2 Cd1 C7 O1 87.1(4) 2_855 . . . ? O1 Cd1 C7 O1 146.5(4) 2_855 . . . ? Cl1 Cd1 C7 O1 -15.9(5) 2_855 . . . ? Cl1 Cd1 C7 O1 -110.1(4) . . . . ? C7 Cd1 C7 O1 112.9(5) 2_855 . . . ? O2 Cd1 C7 O2 -86.6(4) 2_855 . . . ? O1 Cd1 C7 O2 -173.7(7) . . . . ? O1 Cd1 C7 O2 -27.1(5) 2_855 . . . ? Cl1 Cd1 C7 O2 170.4(3) 2_855 . . . ? Cl1 Cd1 C7 O2 76.2(4) . . . . ? C7 Cd1 C7 O2 -60.8(3) 2_855 . . . ? O2 Cd1 C7 C1 -67(4) . . . . ? O2 Cd1 C7 C1 -153(5) 2_855 . . . ? O1 Cd1 C7 C1 120(5) . . . . ? O1 Cd1 C7 C1 -94(5) 2_855 . . . ? Cl1 Cd1 C7 C1 104(5) 2_855 . . . ? Cl1 Cd1 C7 C1 10(5) . . . . ? C7 Cd1 C7 C1 -127(5) 2_855 . . . ? O1 C7 O2 Cd1 -6.6(7) . . . . ? C1 C7 O2 Cd1 173.0(5) . . . . ? O2 Cd1 O2 C7 101.7(4) 2_855 . . . ? O1 Cd1 O2 C7 3.5(4) . . . . ? O1 Cd1 O2 C7 159.0(4) 2_855 . . . ? Cl1 Cd1 O2 C7 -15.7(5) 2_855 . . . ? Cl1 Cd1 O2 C7 -106.4(4) . . . . ? C7 Cd1 O2 C7 130.9(4) 2_855 . . . ? C6 C1 C2 C3 0.5(10) . . . . ? C7 C1 C2 C3 -173.8(6) . . . . ? C4 C3 C2 C1 0.4(10) . . . . ? C12 C3 C2 C1 176.2(6) . . . . ? C2 C1 C6 C5 -1.2(10) . . . . ? C7 C1 C6 C5 173.4(6) . . . . ? C4 C5 C6 C1 0.9(9) . . . . ? C8 C5 C6 C1 -179.1(6) . . . . ? O2 C7 O1 Cd1 6.5(7) . . . . ? C1 C7 O1 Cd1 -173.1(6) . . . . ? O2 Cd1 O1 C7 -3.6(4) . . . . ? O2 Cd1 O1 C7 -101.0(4) 2_855 . . . ? O1 Cd1 O1 C7 -57.6(4) 2_855 . . . ? Cl1 Cd1 O1 C7 166.3(4) 2_855 . . . ? Cl1 Cd1 O1 C7 76.1(4) . . . . ? C7 Cd1 O1 C7 -88.1(6) 2_855 . . . ? C13 N3 C14 C15 0.6(9) . . . . ? C12 N3 C14 C15 171.0(6) . . . . ? N3 C14 C15 N4 -0.8(10) . . . . ? C13 N4 C15 C14 0.7(9) . . . . ? Cd2 N4 C15 C14 -166.9(5) 3_775 . . . ? C9 N1 C8 C5 98.3(7) . . . . ? C11 N1 C8 C5 -87.1(8) . . . . ? C4 C5 C8 N1 71.1(8) . . . . ? C6 C5 C8 N1 -108.9(7) . . . . ? C9 N1 C11 C10 -2.6(9) . . . . ? C8 N1 C11 C10 -178.3(6) . . . . ? C10 N2 C9 N1 -2.1(8) . . . . ? Cd2 N2 C9 N1 176.7(4) 1_445 . . . ? C11 N1 C9 N2 3.0(8) . . . . ? C8 N1 C9 N2 178.5(5) . . . . ? N1 C11 C10 N2 1.5(11) . . . . ? C9 N2 C10 C11 0.3(10) . . . . ? Cd2 N2 C10 C11 -178.6(6) 1_445 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.263 _refine_diff_density_min -2.680 _refine_diff_density_rms 0.113 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 857241' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cd N4 O4' _chemical_formula_sum 'C21 H16 Cd N4 O4' _chemical_formula_weight 500.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 21.3069(15) _cell_length_b 10.2826(7) _cell_length_c 17.8765(12) _cell_angle_alpha 90.00 _cell_angle_beta 99.143(7) _cell_angle_gamma 90.00 _cell_volume 3866.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296 _cell_measurement_reflns_used 2752 _cell_measurement_theta_min 3.0729 _cell_measurement_theta_max 29.2482 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 1.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8001 _exptl_absorpt_correction_T_max 0.8263 _exptl_absorpt_process_details SADABS(2009) _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6902 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3401 _reflns_number_gt 2598 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of 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^)+(0.0263P)^2^+0.4921P] 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 3401 _refine_ls_number_parameters 271 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.047 _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 0.163138(11) -0.25073(2) 0.529027(13) 0.02593(10) Uani 1 1 d U . . N1 N 0.18549(14) 0.6130(3) 0.62867(15) 0.0310(7) Uani 1 1 d . . . N2 N 0.23852(15) 0.4589(3) 0.69680(15) 0.0303(7) Uani 1 1 d . . . N4 N 0.56117(15) 0.2954(3) 0.5596(2) 0.0417(8) Uani 1 1 d . . . N3 N 0.45669(14) 0.3178(3) 0.52681(18) 0.0372(8) Uani 1 1 d . . . O1 O 0.10047(12) -0.3721(3) 0.43535(14) 0.0463(7) Uani 1 1 d . . . O2 O 0.12337(13) -0.1748(3) 0.39981(14) 0.0464(7) Uani 1 1 d U . . O3 O 0.25046(11) -0.1153(2) 0.51840(13) 0.0346(6) Uani 1 1 d . . . O4 O 0.19124(12) -0.0521(2) 0.60064(14) 0.0391(7) Uani 1 1 d . . . C1 C 0.0239(2) -0.1821(4) 0.2814(2) 0.0553(13) Uani 1 1 d . . . H1 H 0.0407 -0.1033 0.3007 0.066 Uiso 1 1 calc R . . C2 C 0.04661(18) -0.2944(4) 0.3149(2) 0.0342(9) Uani 1 1 d . . . C3 C 0.02347(16) -0.4164(3) 0.28361(18) 0.0284(8) Uani 1 1 d . . . C4 C 0.04582(18) -0.5379(4) 0.3141(2) 0.0369(10) Uani 1 1 d . . . H4 H 0.0768 -0.5396 0.3571 0.044 Uiso 1 1 calc R . . C5 C 0.02328(18) -0.6519(4) 0.2823(2) 0.0413(10) Uani 1 1 d . . . H5 H 0.0389 -0.7303 0.3035 0.050 Uiso 1 1 calc R . . C6 C 0.09459(18) -0.2808(4) 0.3873(2) 0.0362(10) Uani 1 1 d . . . C7 C 0.27500(15) 0.0890(3) 0.58057(18) 0.0221(8) Uani 1 1 d . . . C8 C 0.26765(16) 0.1655(3) 0.64270(18) 0.0254(8) Uani 1 1 d . . . H8 H 0.2402 0.1390 0.6753 0.030 Uiso 1 1 calc R . . C9 C 0.30110(17) 0.2813(3) 0.65631(19) 0.0267(8) Uani 1 1 d . . . C10 C 0.34032(16) 0.3204(3) 0.6065(2) 0.0293(9) Uani 1 1 d . . . H10 H 0.3617 0.3993 0.6146 0.035 Uiso 1 1 calc R . . C11 C 0.34883(15) 0.2453(3) 0.5448(2) 0.0265(8) Uani 1 1 d . . . C12 C 0.31624(15) 0.1286(3) 0.53220(18) 0.0240(8) Uani 1 1 d . . . H12 H 0.3220 0.0767 0.4912 0.029 Uiso 1 1 calc R . . C13 C 0.23703(16) -0.0346(3) 0.56602(19) 0.0248(8) Uani 1 1 d . . . C14 C 0.29065(19) 0.3682(3) 0.72158(19) 0.0361(9) Uani 1 1 d . . . H14A H 0.2805 0.3154 0.7630 0.043 Uiso 1 1 calc R . . H14B H 0.3292 0.4164 0.7396 0.043 Uiso 1 1 calc R . . C15 C 0.1763(2) 0.4474(4) 0.7052(2) 0.0442(10) Uani 1 1 d . . . H15 H 0.1592 0.3853 0.7340 0.053 Uiso 1 1 calc R . . C16 C 0.14429(19) 0.5425(4) 0.6643(2) 0.0420(10) Uani 1 1 d . . . H16 H 0.1009 0.5581 0.6606 0.050 Uiso 1 1 calc R . . C17 C 0.24204(18) 0.5590(3) 0.65000(19) 0.0299(9) Uani 1 1 d . . . H17 H 0.2794 0.5872 0.6344 0.036 Uiso 1 1 calc R . . C18 C 0.39168(17) 0.2913(4) 0.4896(2) 0.0350(9) Uani 1 1 d . . . H18A H 0.3927 0.2252 0.4511 0.042 Uiso 1 1 calc R . . H18B H 0.3739 0.3697 0.4646 0.042 Uiso 1 1 calc R . . C19 C 0.47861(19) 0.4240(4) 0.5704(2) 0.0443(10) Uani 1 1 d . . . H19 H 0.4547 0.4935 0.5836 0.053 Uiso 1 1 calc R . . C20 C 0.5427(2) 0.4065(4) 0.5901(2) 0.0489(11) Uani 1 1 d . . . H20 H 0.5697 0.4631 0.6203 0.059 Uiso 1 1 calc R . . C21 C 0.50744(19) 0.2438(4) 0.5224(2) 0.0447(11) Uani 1 1 d . . . H21 H 0.5057 0.1652 0.4964 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02378(15) 0.02532(16) 0.02653(15) -0.00045(13) -0.00266(10) -0.00319(12) N1 0.0372(19) 0.0292(17) 0.0278(16) 0.0026(14) 0.0090(14) 0.0055(15) N2 0.047(2) 0.0223(16) 0.0216(16) 0.0002(14) 0.0056(14) 0.0025(15) N4 0.0265(18) 0.0373(19) 0.061(2) -0.0042(18) 0.0064(17) -0.0008(16) N3 0.0257(18) 0.0363(19) 0.050(2) 0.0061(17) 0.0079(15) -0.0035(16) O1 0.0461(18) 0.0458(17) 0.0393(16) -0.0065(15) -0.0165(13) 0.0073(14) O2 0.0447(17) 0.0539(18) 0.0340(12) 0.0008(13) -0.0142(12) -0.0124(15) O3 0.0336(15) 0.0267(14) 0.0431(16) -0.0129(12) 0.0051(13) -0.0051(12) O4 0.0382(16) 0.0347(15) 0.0479(16) -0.0056(13) 0.0173(13) -0.0157(13) C1 0.066(3) 0.035(2) 0.053(3) -0.002(2) -0.028(2) -0.004(2) C2 0.036(2) 0.036(2) 0.027(2) 0.0001(18) -0.0069(17) -0.0008(18) C3 0.0238(19) 0.035(2) 0.0248(19) 0.0013(17) -0.0008(15) -0.0005(17) C4 0.035(2) 0.044(2) 0.029(2) 0.005(2) -0.0035(17) 0.0040(19) C5 0.043(3) 0.035(2) 0.043(2) 0.003(2) -0.0012(19) 0.005(2) C6 0.027(2) 0.043(3) 0.036(2) -0.009(2) -0.0040(18) 0.0050(18) C7 0.0191(18) 0.0198(18) 0.0255(18) 0.0003(16) -0.0021(14) 0.0013(15) C8 0.029(2) 0.025(2) 0.0222(18) 0.0063(16) 0.0048(15) 0.0033(16) C9 0.030(2) 0.019(2) 0.0286(19) -0.0025(16) -0.0033(16) 0.0054(15) C10 0.026(2) 0.0194(19) 0.039(2) 0.0048(18) -0.0057(17) -0.0023(16) C11 0.0176(17) 0.0261(19) 0.035(2) 0.0041(18) 0.0006(15) 0.0019(17) C12 0.0224(18) 0.0246(19) 0.0249(18) -0.0037(17) 0.0034(15) 0.0044(16) C13 0.026(2) 0.0217(19) 0.0229(19) 0.0043(17) -0.0061(15) -0.0014(16) C14 0.052(3) 0.027(2) 0.027(2) -0.0008(18) -0.0018(18) 0.0075(19) C15 0.052(3) 0.037(2) 0.048(3) 0.010(2) 0.022(2) 0.001(2) C16 0.034(2) 0.048(3) 0.047(3) 0.003(2) 0.0180(19) 0.003(2) C17 0.036(2) 0.027(2) 0.0270(19) -0.0047(18) 0.0073(17) -0.0012(17) C18 0.025(2) 0.042(2) 0.038(2) 0.0075(19) 0.0044(17) -0.0042(17) C19 0.038(3) 0.034(2) 0.062(3) -0.006(2) 0.012(2) -0.004(2) C20 0.040(3) 0.053(3) 0.054(3) -0.008(2) 0.009(2) -0.014(2) C21 0.038(2) 0.039(2) 0.057(3) -0.004(2) 0.008(2) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N1 2.257(3) 1_545 ? Cd1 O1 2.331(2) . ? Cd1 O3 2.356(2) . ? Cd1 N4 2.371(3) 3_445 ? Cd1 O4 2.434(2) . ? Cd1 O2 2.458(2) . ? Cd1 O3 2.550(2) 7_546 ? Cd1 C6 2.734(4) . ? Cd1 C13 2.743(3) . ? N1 C17 1.326(4) . ? N1 C16 1.371(4) . ? N1 Cd1 2.257(3) 1_565 ? N2 C17 1.336(4) . ? N2 C15 1.363(5) . ? N2 C14 1.464(4) . ? N4 C21 1.339(5) . ? N4 C20 1.352(5) . ? N4 Cd1 2.371(3) 3 ? N3 C21 1.335(5) . ? N3 C19 1.379(5) . ? N3 C18 1.464(4) . ? O1 C6 1.266(4) . ? O2 C6 1.253(4) . ? O3 C13 1.254(4) . ? O3 Cd1 2.550(2) 7_546 ? O4 C13 1.249(4) . ? C1 C2 1.354(5) . ? C1 C1 1.390(7) 2 ? C1 H1 0.9300 . ? C2 C3 1.429(4) . ? C2 C6 1.523(5) . ? C3 C4 1.415(4) . ? C3 C3 1.436(6) 2 ? C4 C5 1.358(5) . ? C4 H4 0.9300 . ? C5 C5 1.398(7) 2 ? C5 H5 0.9300 . ? C7 C12 1.388(4) . ? C7 C8 1.390(4) . ? C7 C13 1.507(4) . ? C8 C9 1.389(4) . ? C8 H8 0.9300 . ? C9 C10 1.374(5) . ? C9 C14 1.514(4) . ? C10 C11 1.382(5) . ? C10 H10 0.9300 . ? C11 C12 1.387(4) . ? C11 C18 1.522(5) . ? C12 H12 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.341(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.366(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 O1 105.03(10) 1_545 . ? N1 Cd1 O3 111.12(10) 1_545 . ? O1 Cd1 O3 128.92(9) . . ? N1 Cd1 N4 91.63(11) 1_545 3_445 ? O1 Cd1 N4 80.29(10) . 3_445 ? O3 Cd1 N4 131.67(9) . 3_445 ? N1 Cd1 O4 95.87(9) 1_545 . ? O1 Cd1 O4 153.13(9) . . ? O3 Cd1 O4 54.20(8) . . ? N4 Cd1 O4 82.47(10) 3_445 . ? N1 Cd1 O2 159.54(10) 1_545 . ? O1 Cd1 O2 54.72(9) . . ? O3 Cd1 O2 83.99(8) . . ? N4 Cd1 O2 87.78(11) 3_445 . ? O4 Cd1 O2 104.31(9) . . ? N1 Cd1 O3 81.61(9) 1_545 7_546 ? O1 Cd1 O3 80.40(8) . 7_546 ? O3 Cd1 O3 70.81(9) . 7_546 ? N4 Cd1 O3 157.09(10) 3_445 7_546 ? O4 Cd1 O3 119.86(8) . 7_546 ? O2 Cd1 O3 91.05(9) . 7_546 ? N1 Cd1 C6 132.52(11) 1_545 . ? O1 Cd1 C6 27.49(9) . . ? O3 Cd1 C6 107.74(10) . . ? N4 Cd1 C6 82.07(12) 3_445 . ? O4 Cd1 C6 129.28(10) . . ? O2 Cd1 C6 27.28(10) . . ? O3 Cd1 C6 86.45(9) 7_546 . ? N1 Cd1 C13 105.76(10) 1_545 . ? O1 Cd1 C13 148.03(10) . . ? O3 Cd1 C13 27.13(9) . . ? N4 Cd1 C13 107.12(11) 3_445 . ? O4 Cd1 C13 27.08(9) . . ? O2 Cd1 C13 93.92(9) . . ? O3 Cd1 C13 95.78(10) 7_546 . ? C6 Cd1 C13 121.12(11) . . ? C17 N1 C16 105.3(3) . . ? C17 N1 Cd1 123.7(2) . 1_565 ? C16 N1 Cd1 128.6(3) . 1_565 ? C17 N2 C15 106.8(3) . . ? C17 N2 C14 124.4(3) . . ? C15 N2 C14 128.0(3) . . ? C21 N4 C20 104.7(3) . . ? C21 N4 Cd1 123.3(3) . 3 ? C20 N4 Cd1 126.8(3) . 3 ? C21 N3 C19 106.3(3) . . ? C21 N3 C18 125.7(3) . . ? C19 N3 C18 128.0(3) . . ? C6 O1 Cd1 94.3(2) . . ? C6 O2 Cd1 88.7(2) . . ? C13 O3 Cd1 93.9(2) . . ? C13 O3 Cd1 146.9(2) . 7_546 ? Cd1 O3 Cd1 109.19(9) . 7_546 ? C13 O4 Cd1 90.4(2) . . ? C2 C1 C1 121.4(2) . 2 ? C2 C1 H1 119.3 . . ? C1 C1 H1 119.3 2 . ? C1 C2 C3 119.9(3) . . ? C1 C2 C6 116.2(3) . . ? C3 C2 C6 123.8(3) . . ? C4 C3 C2 123.4(3) . . ? C4 C3 C3 118.01(19) . 2 ? C2 C3 C3 118.58(19) . 2 ? C5 C4 C3 121.7(3) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C5 120.2(2) . 2 ? C4 C5 H5 119.9 . . ? C5 C5 H5 119.9 2 . ? O2 C6 O1 122.1(3) . . ? O2 C6 C2 118.3(4) . . ? O1 C6 C2 119.3(3) . . ? O2 C6 Cd1 64.00(19) . . ? O1 C6 Cd1 58.25(18) . . ? C2 C6 Cd1 170.3(3) . . ? C12 C7 C8 119.7(3) . . ? C12 C7 C13 121.0(3) . . ? C8 C7 C13 119.3(3) . . ? C9 C8 C7 120.3(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 119.0(3) . . ? C10 C9 C14 120.4(3) . . ? C8 C9 C14 120.4(3) . . ? C9 C10 C11 121.6(3) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C10 C11 C12 119.1(3) . . ? C10 C11 C18 120.8(3) . . ? C12 C11 C18 120.0(3) . . ? C11 C12 C7 120.2(3) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? O4 C13 O3 121.5(3) . . ? O4 C13 C7 118.4(3) . . ? O3 C13 C7 120.1(3) . . ? O4 C13 Cd1 62.54(18) . . ? O3 C13 Cd1 58.98(17) . . ? C7 C13 Cd1 175.4(2) . . ? N2 C14 C9 109.9(3) . . ? N2 C14 H14A 109.7 . . ? C9 C14 H14A 109.7 . . ? N2 C14 H14B 109.7 . . ? C9 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C16 C15 N2 107.2(3) . . ? C16 C15 H15 126.4 . . ? N2 C15 H15 126.4 . . ? C15 C16 N1 109.3(4) . . ? C15 C16 H16 125.3 . . ? N1 C16 H16 125.3 . . ? N1 C17 N2 111.3(3) . . ? N1 C17 H17 124.3 . . ? N2 C17 H17 124.3 . . ? N3 C18 C11 112.7(3) . . ? N3 C18 H18A 109.1 . . ? C11 C18 H18A 109.1 . . ? N3 C18 H18B 109.1 . . ? C11 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C20 C19 N3 106.0(4) . . ? C20 C19 H19 127.0 . . ? N3 C19 H19 127.0 . . ? N4 C20 C19 110.5(4) . . ? N4 C20 H20 124.7 . . ? C19 C20 H20 124.7 . . ? N3 C21 N4 112.4(3) . . ? N3 C21 H21 123.8 . . ? N4 C21 H21 123.8 . . ? 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 N1 Cd1 O1 C6 -179.4(2) 1_545 . . . ? O3 Cd1 O1 C6 -45.3(3) . . . . ? N4 Cd1 O1 C6 91.5(2) 3_445 . . . ? O4 Cd1 O1 C6 40.7(3) . . . . ? O2 Cd1 O1 C6 -2.7(2) . . . . ? O3 Cd1 O1 C6 -100.9(2) 7_546 . . . ? C13 Cd1 O1 C6 -15.4(3) . . . . ? N1 Cd1 O2 C6 11.8(4) 1_545 . . . ? O1 Cd1 O2 C6 2.7(2) . . . . ? O3 Cd1 O2 C6 150.8(2) . . . . ? N4 Cd1 O2 C6 -76.9(2) 3_445 . . . ? O4 Cd1 O2 C6 -158.6(2) . . . . ? O3 Cd1 O2 C6 80.2(2) 7_546 . . . ? C13 Cd1 O2 C6 176.0(2) . . . . ? N1 Cd1 O3 C13 -83.4(2) 1_545 . . . ? O1 Cd1 O3 C13 144.61(18) . . . . ? N4 Cd1 O3 C13 29.2(2) 3_445 . . . ? O4 Cd1 O3 C13 -1.62(18) . . . . ? O2 Cd1 O3 C13 110.9(2) . . . . ? O3 Cd1 O3 C13 -155.9(2) 7_546 . . . ? C6 Cd1 O3 C13 124.5(2) . . . . ? N1 Cd1 O3 Cd1 72.54(11) 1_545 . . 7_546 ? O1 Cd1 O3 Cd1 -59.47(14) . . . 7_546 ? N4 Cd1 O3 Cd1 -174.84(11) 3_445 . . 7_546 ? O4 Cd1 O3 Cd1 154.30(14) . . . 7_546 ? O2 Cd1 O3 Cd1 -93.22(10) . . . 7_546 ? O3 Cd1 O3 Cd1 0.0 7_546 . . 7_546 ? C6 Cd1 O3 Cd1 -79.63(12) . . . 7_546 ? C13 Cd1 O3 Cd1 155.9(2) . . . 7_546 ? N1 Cd1 O4 C13 113.5(2) 1_545 . . . ? O1 Cd1 O4 C13 -105.2(3) . . . . ? O3 Cd1 O4 C13 1.62(18) . . . . ? N4 Cd1 O4 C13 -155.6(2) 3_445 . . . ? O2 Cd1 O4 C13 -69.9(2) . . . . ? O3 Cd1 O4 C13 29.8(2) 7_546 . . . ? C6 Cd1 O4 C13 -82.4(2) . . . . ? C1 C1 C2 C3 3.0(8) 2 . . . ? C1 C1 C2 C6 -174.6(6) 2 . . . ? C1 C2 C3 C4 178.4(4) . . . . ? C6 C2 C3 C4 -4.2(6) . . . . ? C1 C2 C3 C3 0.4(7) . . . 2 ? C6 C2 C3 C3 177.8(4) . . . 2 ? C2 C3 C4 C5 -179.1(4) . . . . ? C3 C3 C4 C5 -1.1(6) 2 . . . ? C3 C4 C5 C5 -0.1(7) . . . 2 ? Cd1 O2 C6 O1 -4.8(4) . . . . ? Cd1 O2 C6 C2 169.4(3) . . . . ? Cd1 O1 C6 O2 5.1(4) . . . . ? Cd1 O1 C6 C2 -169.1(3) . . . . ? C1 C2 C6 O2 -19.9(6) . . . . ? C3 C2 C6 O2 162.7(4) . . . . ? C1 C2 C6 O1 154.6(4) . . . . ? C3 C2 C6 O1 -22.9(6) . . . . ? C1 C2 C6 Cd1 81.6(17) . . . . ? C3 C2 C6 Cd1 -95.8(17) . . . . ? N1 Cd1 C6 O2 -174.4(2) 1_545 . . . ? O1 Cd1 C6 O2 -175.2(4) . . . . ? O3 Cd1 C6 O2 -30.7(2) . . . . ? N4 Cd1 C6 O2 100.6(2) 3_445 . . . ? O4 Cd1 C6 O2 27.2(3) . . . . ? O3 Cd1 C6 O2 -99.2(2) 7_546 . . . ? C13 Cd1 C6 O2 -4.6(3) . . . . ? N1 Cd1 C6 O1 0.7(3) 1_545 . . . ? O3 Cd1 C6 O1 144.5(2) . . . . ? N4 Cd1 C6 O1 -84.2(2) 3_445 . . . ? O4 Cd1 C6 O1 -157.63(19) . . . . ? O2 Cd1 C6 O1 175.2(4) . . . . ? O3 Cd1 C6 O1 75.9(2) 7_546 . . . ? C13 Cd1 C6 O1 170.6(2) . . . . ? N1 Cd1 C6 C2 79.2(17) 1_545 . . . ? O1 Cd1 C6 C2 78.5(17) . . . . ? O3 Cd1 C6 C2 -137.0(17) . . . . ? N4 Cd1 C6 C2 -5.7(17) 3_445 . . . ? O4 Cd1 C6 C2 -79.2(17) . . . . ? O2 Cd1 C6 C2 -106.4(17) . . . . ? O3 Cd1 C6 C2 154.4(17) 7_546 . . . ? C13 Cd1 C6 C2 -111.0(17) . . . . ? C12 C7 C8 C9 0.3(5) . . . . ? C13 C7 C8 C9 -178.6(3) . . . . ? C7 C8 C9 C10 1.5(5) . . . . ? C7 C8 C9 C14 176.8(3) . . . . ? C8 C9 C10 C11 -2.1(5) . . . . ? C14 C9 C10 C11 -177.5(3) . . . . ? C9 C10 C11 C12 1.0(5) . . . . ? C9 C10 C11 C18 179.1(3) . . . . ? C10 C11 C12 C7 0.9(5) . . . . ? C18 C11 C12 C7 -177.2(3) . . . . ? C8 C7 C12 C11 -1.5(5) . . . . ? C13 C7 C12 C11 177.4(3) . . . . ? Cd1 O4 C13 O3 -2.9(3) . . . . ? Cd1 O4 C13 C7 174.9(2) . . . . ? Cd1 O3 C13 O4 3.0(3) . . . . ? Cd1 O3 C13 O4 -132.1(4) 7_546 . . . ? Cd1 O3 C13 C7 -174.8(2) . . . . ? Cd1 O3 C13 C7 50.1(5) 7_546 . . . ? Cd1 O3 C13 Cd1 -135.1(4) 7_546 . . . ? C12 C7 C13 O4 -164.8(3) . . . . ? C8 C7 C13 O4 14.0(4) . . . . ? C12 C7 C13 O3 13.0(5) . . . . ? C8 C7 C13 O3 -168.1(3) . . . . ? C12 C7 C13 Cd1 -64(3) . . . . ? C8 C7 C13 Cd1 115(3) . . . . ? N1 Cd1 C13 O4 -71.4(2) 1_545 . . . ? O1 Cd1 C13 O4 124.6(2) . . . . ? O3 Cd1 C13 O4 -177.1(3) . . . . ? N4 Cd1 C13 O4 25.3(2) 3_445 . . . ? O2 Cd1 C13 O4 114.2(2) . . . . ? O3 Cd1 C13 O4 -154.3(2) 7_546 . . . ? C6 Cd1 C13 O4 116.3(2) . . . . ? N1 Cd1 C13 O3 105.68(19) 1_545 . . . ? O1 Cd1 C13 O3 -58.3(3) . . . . ? N4 Cd1 C13 O3 -157.55(19) 3_445 . . . ? O4 Cd1 C13 O3 177.1(3) . . . . ? O2 Cd1 C13 O3 -68.67(19) . . . . ? O3 Cd1 C13 O3 22.8(2) 7_546 . . . ? C6 Cd1 C13 O3 -66.6(2) . . . . ? N1 Cd1 C13 C7 -175(3) 1_545 . . . ? O1 Cd1 C13 C7 21(3) . . . . ? O3 Cd1 C13 C7 79(3) . . . . ? N4 Cd1 C13 C7 -78(3) 3_445 . . . ? O4 Cd1 C13 C7 -104(3) . . . . ? O2 Cd1 C13 C7 11(3) . . . . ? O3 Cd1 C13 C7 102(3) 7_546 . . . ? C6 Cd1 C13 C7 13(3) . . . . ? C17 N2 C14 C9 -71.2(4) . . . . ? C15 N2 C14 C9 96.9(4) . . . . ? C10 C9 C14 N2 86.9(4) . . . . ? C8 C9 C14 N2 -88.4(4) . . . . ? C17 N2 C15 C16 -1.1(4) . . . . ? C14 N2 C15 C16 -170.9(3) . . . . ? N2 C15 C16 N1 1.1(4) . . . . ? C17 N1 C16 C15 -0.7(4) . . . . ? Cd1 N1 C16 C15 162.2(2) 1_565 . . . ? C16 N1 C17 N2 0.0(4) . . . . ? Cd1 N1 C17 N2 -164.0(2) 1_565 . . . ? C15 N2 C17 N1 0.7(4) . . . . ? C14 N2 C17 N1 170.9(3) . . . . ? C21 N3 C18 C11 106.4(4) . . . . ? C19 N3 C18 C11 -76.2(5) . . . . ? C10 C11 C18 N3 57.2(4) . . . . ? C12 C11 C18 N3 -124.8(3) . . . . ? C21 N3 C19 C20 -0.2(4) . . . . ? C18 N3 C19 C20 -178.0(4) . . . . ? C21 N4 C20 C19 -1.4(5) . . . . ? Cd1 N4 C20 C19 153.5(3) 3 . . . ? N3 C19 C20 N4 1.0(5) . . . . ? C19 N3 C21 N4 -0.6(5) . . . . ? C18 N3 C21 N4 177.2(3) . . . . ? C20 N4 C21 N3 1.2(5) . . . . ? Cd1 N4 C21 N3 -154.8(3) 3 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.408 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.073