# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_12033 _database_code_depnum_ccdc_archive 'CCDC 874326' #TrackingRef 'bpbp.cif' _audit_creation_method SHELXL-97 #============================================================================= loop_ _chemical_name_common ; 2,6-bis(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridine ; _chemical_melting_point ? _chemical_formula_moiety 'C31 H21 N5' _chemical_formula_sum 'C31 H21 N5' _chemical_formula_weight 463.53 _chemical_name_systematic ; 2,6-bis(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridine ; 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.9303(12) _cell_length_b 11.0153(12) _cell_length_c 19.836(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2388.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5708 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 26.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9822 _exptl_absorpt_process_details 'SADABS (Bruker, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13313 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.05 _reflns_number_total 2618 _reflns_number_gt 2087 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0387P)^2^+0.7530P] 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 2618 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 N1 N 0.5000 0.56589(13) 0.2500 0.0287(3) Uani 1 2 d S . . C1 C 0.5000 0.81869(16) 0.2500 0.0370(4) Uani 1 2 d S . . H1 H 0.5000 0.9049 0.2500 0.044 Uiso 1 2 calc SR . . C2 C 0.41299(12) 0.75516(11) 0.28602(6) 0.0335(3) Uani 1 1 d . . . H2 H 0.3503 0.7966 0.3099 0.040 Uiso 1 1 calc R . . C3 C 0.41925(11) 0.62943(11) 0.28651(6) 0.0281(3) Uani 1 1 d . . . C4 C 0.33562(11) 0.55869(10) 0.32969(6) 0.0283(3) Uani 1 1 d . . . N3 N 0.21904(9) 0.58335(9) 0.33840(5) 0.0313(2) Uani 1 1 d . . . C5 C 0.17859(11) 0.49568(11) 0.38352(6) 0.0297(3) Uani 1 1 d . . . C6 C 0.06125(11) 0.47533(12) 0.40931(7) 0.0361(3) Uani 1 1 d . . . H6 H -0.0051 0.5270 0.3978 0.043 Uiso 1 1 calc R . . C7 C 0.04521(12) 0.37804(13) 0.45176(7) 0.0392(3) Uani 1 1 d . . . H7 H -0.0339 0.3625 0.4697 0.047 Uiso 1 1 calc R . . C8 C 0.14185(12) 0.30129(13) 0.46932(6) 0.0391(3) Uani 1 1 d . . . H8 H 0.1268 0.2349 0.4987 0.047 Uiso 1 1 calc R . . C9 C 0.25932(12) 0.31964(12) 0.44485(6) 0.0346(3) Uani 1 1 d . . . H9 H 0.3254 0.2681 0.4570 0.042 Uiso 1 1 calc R . . C10 C 0.27473(10) 0.41790(11) 0.40155(6) 0.0288(3) Uani 1 1 d . . . N2 N 0.37568(9) 0.45996(9) 0.36634(5) 0.0290(2) Uani 1 1 d . . . C11 C 0.49841(11) 0.41395(11) 0.37044(6) 0.0297(3) Uani 1 1 d . . . C12 C 0.52621(11) 0.30339(12) 0.34132(7) 0.0355(3) Uani 1 1 d . . . H12 H 0.4638 0.2552 0.3214 0.043 Uiso 1 1 calc R . . C13 C 0.64667(12) 0.26399(14) 0.34160(7) 0.0440(3) Uani 1 1 d . . . H13 H 0.6672 0.1886 0.3213 0.053 Uiso 1 1 calc R . . C14 C 0.73711(12) 0.33372(15) 0.37119(8) 0.0465(4) Uani 1 1 d . . . H14 H 0.8197 0.3068 0.3704 0.056 Uiso 1 1 calc R . . C15 C 0.70787(12) 0.44211(14) 0.40188(8) 0.0466(4) Uani 1 1 d . . . H15 H 0.7699 0.4889 0.4231 0.056 Uiso 1 1 calc R . . C16 C 0.58758(12) 0.48292(13) 0.40175(7) 0.0384(3) Uani 1 1 d . . . H16 H 0.5668 0.5574 0.4230 0.046 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 N1 0.0285(7) 0.0266(7) 0.0309(7) 0.000 0.0038(6) 0.000 C1 0.0477(11) 0.0241(9) 0.0392(10) 0.000 0.0070(8) 0.000 C2 0.0364(7) 0.0300(6) 0.0341(6) -0.0027(5) 0.0057(5) 0.0043(5) C3 0.0272(6) 0.0287(6) 0.0283(6) -0.0012(5) 0.0013(5) -0.0005(5) C4 0.0294(6) 0.0259(6) 0.0298(6) -0.0034(5) 0.0031(5) 0.0004(5) N3 0.0292(5) 0.0293(5) 0.0354(5) -0.0022(4) 0.0064(4) 0.0016(4) C5 0.0296(6) 0.0294(6) 0.0301(6) -0.0055(5) 0.0040(5) -0.0017(5) C6 0.0293(6) 0.0391(7) 0.0400(7) -0.0053(6) 0.0070(5) 0.0001(5) C7 0.0326(7) 0.0481(8) 0.0370(7) -0.0038(6) 0.0110(6) -0.0084(6) C8 0.0423(7) 0.0443(8) 0.0307(6) 0.0033(6) 0.0035(6) -0.0110(6) C9 0.0348(7) 0.0385(7) 0.0306(6) 0.0026(5) -0.0018(5) -0.0036(6) C10 0.0259(6) 0.0329(6) 0.0277(6) -0.0042(5) 0.0014(5) -0.0048(5) N2 0.0247(5) 0.0309(5) 0.0315(5) 0.0012(4) 0.0022(4) -0.0013(4) C11 0.0239(6) 0.0345(6) 0.0306(6) 0.0053(5) 0.0025(5) -0.0009(5) C12 0.0316(6) 0.0380(7) 0.0370(7) 0.0000(6) 0.0001(5) 0.0000(6) C13 0.0402(8) 0.0468(8) 0.0450(8) 0.0013(6) 0.0051(6) 0.0110(6) C14 0.0263(7) 0.0636(10) 0.0496(8) 0.0117(7) 0.0050(6) 0.0049(6) C15 0.0284(7) 0.0565(9) 0.0549(9) 0.0067(7) -0.0025(6) -0.0097(6) C16 0.0326(7) 0.0387(7) 0.0440(8) 0.0002(6) -0.0003(6) -0.0056(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.3393(14) 3_655 ? N1 C3 1.3393(14) . ? C1 C2 1.3801(15) 3_655 ? C1 C2 1.3801(15) . ? C1 H1 0.9500 . ? C2 C3 1.3866(17) . ? C2 H2 0.9500 . ? C3 C4 1.4752(16) . ? C4 N3 1.3144(15) . ? C4 N2 1.3794(15) . ? N3 C5 1.3890(16) . ? C5 C6 1.3988(17) . ? C5 C10 1.4023(17) . ? C6 C7 1.3742(19) . ? C6 H6 0.9500 . ? C7 C8 1.397(2) . ? C7 H7 0.9500 . ? C8 C9 1.3874(18) . ? C8 H8 0.9500 . ? C9 C10 1.3920(17) . ? C9 H9 0.9500 . ? C10 N2 1.3857(14) . ? N2 C11 1.4364(15) . ? C11 C12 1.3818(18) . ? C11 C16 1.3830(18) . ? C12 C13 1.3864(18) . ? C12 H12 0.9500 . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 C15 1.378(2) . ? C14 H14 0.9500 . ? C15 C16 1.3896(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C3 N1 C3 116.98(14) 3_655 . ? C2 C1 C2 119.07(16) 3_655 . ? C2 C1 H1 120.5 3_655 . ? C2 C1 H1 120.5 . . ? C1 C2 C3 118.43(12) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? N1 C3 C2 123.41(11) . . ? N1 C3 C4 116.50(11) . . ? C2 C3 C4 120.08(11) . . ? N3 C4 N2 113.67(10) . . ? N3 C4 C3 124.60(11) . . ? N2 C4 C3 121.72(10) . . ? C4 N3 C5 104.46(10) . . ? N3 C5 C6 129.71(12) . . ? N3 C5 C10 110.52(10) . . ? C6 C5 C10 119.73(12) . . ? C7 C6 C5 117.77(12) . . ? C7 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? C6 C7 C8 121.89(12) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C7 121.62(12) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 116.17(12) . . ? C8 C9 H9 121.9 . . ? C10 C9 H9 121.9 . . ? N2 C10 C9 131.86(11) . . ? N2 C10 C5 105.30(10) . . ? C9 C10 C5 122.81(11) . . ? C4 N2 C10 106.05(9) . . ? C4 N2 C11 127.19(10) . . ? C10 N2 C11 126.67(10) . . ? C12 C11 C16 121.13(12) . . ? C12 C11 N2 119.51(11) . . ? C16 C11 N2 119.33(11) . . ? C11 C12 C13 118.88(12) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 120.46(14) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 120.21(13) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.93(13) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 119.34(13) . . ? C11 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? 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 C2 C1 C2 C3 2.30(8) 3_655 . . . ? C3 N1 C3 C2 2.52(9) 3_655 . . . ? C3 N1 C3 C4 -176.43(12) 3_655 . . . ? C1 C2 C3 N1 -4.94(18) . . . . ? C1 C2 C3 C4 173.98(10) . . . . ? N1 C3 C4 N3 -140.05(11) . . . . ? C2 C3 C4 N3 40.96(18) . . . . ? N1 C3 C4 N2 41.42(15) . . . . ? C2 C3 C4 N2 -137.57(12) . . . . ? N2 C4 N3 C5 -0.11(13) . . . . ? C3 C4 N3 C5 -178.74(11) . . . . ? C4 N3 C5 C6 -177.78(13) . . . . ? C4 N3 C5 C10 0.06(13) . . . . ? N3 C5 C6 C7 177.49(12) . . . . ? C10 C5 C6 C7 -0.18(18) . . . . ? C5 C6 C7 C8 0.2(2) . . . . ? C6 C7 C8 C9 0.2(2) . . . . ? C7 C8 C9 C10 -0.54(19) . . . . ? C8 C9 C10 N2 -177.24(12) . . . . ? C8 C9 C10 C5 0.57(18) . . . . ? N3 C5 C10 N2 0.01(13) . . . . ? C6 C5 C10 N2 178.09(11) . . . . ? N3 C5 C10 C9 -178.30(11) . . . . ? C6 C5 C10 C9 -0.22(18) . . . . ? N3 C4 N2 C10 0.11(13) . . . . ? C3 C4 N2 C10 178.79(10) . . . . ? N3 C4 N2 C11 -176.61(11) . . . . ? C3 C4 N2 C11 2.07(18) . . . . ? C9 C10 N2 C4 178.02(13) . . . . ? C5 C10 N2 C4 -0.07(12) . . . . ? C9 C10 N2 C11 -5.2(2) . . . . ? C5 C10 N2 C11 176.67(11) . . . . ? C4 N2 C11 C12 -110.83(14) . . . . ? C10 N2 C11 C12 73.10(16) . . . . ? C4 N2 C11 C16 67.22(17) . . . . ? C10 N2 C11 C16 -108.85(14) . . . . ? C16 C11 C12 C13 -2.41(19) . . . . ? N2 C11 C12 C13 175.61(12) . . . . ? C11 C12 C13 C14 0.7(2) . . . . ? C12 C13 C14 C15 1.3(2) . . . . ? C13 C14 C15 C16 -1.5(2) . . . . ? C12 C11 C16 C15 2.2(2) . . . . ? N2 C11 C16 C15 -175.83(12) . . . . ? C14 C15 C16 C11 -0.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.215 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.034 data_02251 _database_code_depnum_ccdc_archive 'CCDC 874327' #TrackingRef 'complex 1.cif' _audit_creation_method SHELXL-97 #============================================================================= _chemical_name_systematic ; N,N-bis(phenyl)-2,6-bis-(benzimidazol-2-yl)pyridine dichoride zinc(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H21 Cl2 N5 Zn' _chemical_formula_sum 'C31 H21 Cl2 N5 Zn' _chemical_formula_weight 599.80 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' Cl Cl 0.1484 0.1585 '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 Cc _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' _cell_length_a 15.743(2) _cell_length_b 9.4359(14) _cell_length_c 17.663(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.993(2) _cell_angle_gamma 90.00 _cell_volume 2623.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4191 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.01 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 1.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6267 _exptl_absorpt_correction_T_max 0.8626 _exptl_absorpt_process_details 'SADABS (Bruker, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _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 7229 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.02 _reflns_number_total 3936 _reflns_number_gt 3564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0249P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(13) _refine_ls_number_reflns 3936 _refine_ls_number_parameters 353 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0663 _refine_ls_wR_factor_gt 0.0631 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.094 _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 0.81692(2) -0.01175(3) -0.03322(2) 0.02168(9) Uani 1 1 d . . . N1 N 0.90446(17) -0.1741(3) 0.00067(15) 0.0238(6) Uani 1 1 d . . . C1 C 0.9168(2) -0.3124(3) -0.02330(18) 0.0241(7) Uani 1 1 d . . . C2 C 0.8817(2) -0.3850(4) -0.08515(19) 0.0311(8) Uani 1 1 d . . . H2 H 0.8451 -0.3390 -0.1207 0.037 Uiso 1 1 calc R . . C3 C 0.9021(2) -0.5251(4) -0.0924(2) 0.0346(8) Uani 1 1 d . . . H3 H 0.8788 -0.5780 -0.1335 0.041 Uiso 1 1 calc R . . C4 C 0.9571(2) -0.5925(4) -0.0399(2) 0.0332(8) Uani 1 1 d . . . H4 H 0.9694 -0.6902 -0.0465 0.040 Uiso 1 1 calc R . . C5 C 0.9935(2) -0.5217(3) 0.0203(2) 0.0270(7) Uani 1 1 d . . . H5 H 1.0310 -0.5676 0.0552 0.032 Uiso 1 1 calc R . . C6 C 0.9726(2) -0.3797(3) 0.02753(18) 0.0229(6) Uani 1 1 d . . . N2 N 0.99400(16) -0.2786(3) 0.08303(14) 0.0222(5) Uani 1 1 d . . . C7 C 1.0448(2) -0.3100(3) 0.14960(18) 0.0240(7) Uani 1 1 d . . . C8 C 1.1209(2) -0.3820(3) 0.13923(19) 0.0265(7) Uani 1 1 d . . . H8 H 1.1398 -0.4041 0.0898 0.032 Uiso 1 1 calc R . . C9 C 1.1686(2) -0.4208(4) 0.2031(2) 0.0357(9) Uani 1 1 d . . . H9 H 1.2201 -0.4719 0.1975 0.043 Uiso 1 1 calc R . . C10 C 1.1414(3) -0.3854(4) 0.2749(2) 0.0403(10) Uani 1 1 d . . . H10 H 1.1751 -0.4100 0.3181 0.048 Uiso 1 1 calc R . . C11 C 1.0660(3) -0.3149(4) 0.2838(2) 0.0412(9) Uani 1 1 d . . . H11 H 1.0479 -0.2908 0.3332 0.049 Uiso 1 1 calc R . . C12 C 1.0154(2) -0.2780(3) 0.22086(19) 0.0305(8) Uani 1 1 d . . . H12 H 0.9622 -0.2323 0.2270 0.037 Uiso 1 1 calc R . . C13 C 0.95018(19) -0.1574(3) 0.06324(18) 0.0232(7) Uani 1 1 d . . . N3 N 0.88413(16) 0.0609(3) 0.07248(15) 0.0229(6) Uani 1 1 d . . . C14 C 0.9485(2) -0.0166(3) 0.10072(18) 0.0235(7) Uani 1 1 d . . . C15 C 1.0046(2) 0.0381(4) 0.1547(2) 0.0303(8) Uani 1 1 d . . . H15 H 1.0511 -0.0162 0.1735 0.036 Uiso 1 1 calc R . . C16 C 0.9902(2) 0.1753(4) 0.18015(19) 0.0316(8) Uani 1 1 d . . . H16 H 1.0278 0.2157 0.2168 0.038 Uiso 1 1 calc R . . C17 C 0.9220(2) 0.2541(3) 0.15300(19) 0.0286(7) Uani 1 1 d . . . H17 H 0.9112 0.3468 0.1715 0.034 Uiso 1 1 calc R . . C18 C 0.8700(2) 0.1926(3) 0.09765(17) 0.0233(7) Uani 1 1 d . . . N4 N 0.76624(17) 0.1902(3) -0.00407(15) 0.0239(6) Uani 1 1 d . . . C19 C 0.7978(2) 0.2583(3) 0.05540(18) 0.0230(7) Uani 1 1 d . . . N5 N 0.75819(17) 0.3848(3) 0.06775(14) 0.0221(6) Uani 1 1 d . . . C20 C 0.7632(2) 0.4811(3) 0.13096(18) 0.0226(7) Uani 1 1 d . . . C21 C 0.7448(2) 0.4336(3) 0.20285(19) 0.0269(7) Uani 1 1 d . . . H21 H 0.7329 0.3363 0.2116 0.032 Uiso 1 1 calc R . . C22 C 0.7439(2) 0.5307(4) 0.2623(2) 0.0357(9) Uani 1 1 d . . . H22 H 0.7312 0.4998 0.3120 0.043 Uiso 1 1 calc R . . C23 C 0.7613(2) 0.6711(4) 0.2490(2) 0.0353(9) Uani 1 1 d . . . H23 H 0.7611 0.7368 0.2898 0.042 Uiso 1 1 calc R . . C24 C 0.7789(2) 0.7174(3) 0.1770(2) 0.0337(8) Uani 1 1 d . . . H24 H 0.7907 0.8147 0.1684 0.040 Uiso 1 1 calc R . . C25 C 0.7795(2) 0.6224(3) 0.1170(2) 0.0287(7) Uani 1 1 d . . . H25 H 0.7908 0.6542 0.0671 0.034 Uiso 1 1 calc R . . C26 C 0.6954(2) 0.3975(3) 0.01089(18) 0.0227(7) Uani 1 1 d . . . C27 C 0.6359(2) 0.5034(3) -0.0041(2) 0.0262(7) Uani 1 1 d . . . H27 H 0.6339 0.5883 0.0247 0.031 Uiso 1 1 calc R . . C28 C 0.5800(2) 0.4769(4) -0.0635(2) 0.0306(8) Uani 1 1 d . . . H28 H 0.5386 0.5465 -0.0766 0.037 Uiso 1 1 calc R . . C29 C 0.5822(2) 0.3508(4) -0.10508(19) 0.0293(8) Uani 1 1 d . . . H29 H 0.5408 0.3356 -0.1441 0.035 Uiso 1 1 calc R . . C30 C 0.6424(2) 0.2483(3) -0.09118(18) 0.0271(7) Uani 1 1 d . . . H30 H 0.6441 0.1637 -0.1202 0.033 Uiso 1 1 calc R . . C31 C 0.7010(2) 0.2738(3) -0.03247(17) 0.0218(7) Uani 1 1 d . . . Cl1 Cl 0.69555(5) -0.13677(8) -0.02275(5) 0.0335(2) Uani 1 1 d . . . Cl2 Cl 0.86538(6) 0.03602(10) -0.15099(5) 0.0379(2) 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 0.02233(17) 0.02280(18) 0.01983(17) -0.00015(17) -0.00223(12) 0.00208(17) N1 0.0244(14) 0.0244(14) 0.0226(14) 0.0010(11) -0.0015(11) 0.0023(11) C1 0.0197(16) 0.0250(16) 0.0276(18) 0.0021(13) 0.0028(13) 0.0031(13) C2 0.032(2) 0.0359(19) 0.0253(19) -0.0020(14) -0.0035(15) 0.0035(15) C3 0.033(2) 0.039(2) 0.031(2) -0.0127(15) -0.0029(16) 0.0025(16) C4 0.036(2) 0.0260(17) 0.037(2) -0.0051(16) 0.0029(16) 0.0090(15) C5 0.0252(18) 0.0258(17) 0.0303(19) 0.0028(13) 0.0027(14) 0.0043(13) C6 0.0216(16) 0.0243(15) 0.0229(16) 0.0004(12) 0.0044(12) 0.0020(13) N2 0.0220(14) 0.0256(13) 0.0191(13) 0.0026(10) 0.0007(11) 0.0051(11) C7 0.0268(17) 0.0225(15) 0.0224(16) 0.0055(12) -0.0026(13) -0.0004(13) C8 0.0282(18) 0.0201(15) 0.0313(19) 0.0037(13) -0.0026(14) 0.0019(13) C9 0.033(2) 0.0241(17) 0.050(2) 0.0070(16) -0.0112(17) 0.0032(15) C10 0.050(2) 0.033(2) 0.037(2) 0.0152(16) -0.0204(19) -0.0059(18) C11 0.059(3) 0.042(2) 0.0221(19) 0.0050(16) 0.0007(17) -0.009(2) C12 0.0338(19) 0.0346(19) 0.0232(17) 0.0042(15) 0.0000(14) 0.0009(15) C13 0.0211(16) 0.0256(16) 0.0230(17) 0.0030(13) 0.0040(13) 0.0020(13) N3 0.0198(13) 0.0239(13) 0.0249(14) 0.0028(11) -0.0015(11) 0.0038(11) C14 0.0251(17) 0.0247(16) 0.0208(16) 0.0007(12) 0.0006(13) 0.0008(13) C15 0.0285(18) 0.0346(18) 0.0276(19) 0.0043(15) -0.0045(14) 0.0031(15) C16 0.0324(19) 0.0332(18) 0.0286(19) -0.0035(14) -0.0114(15) -0.0011(16) C17 0.0346(19) 0.0237(16) 0.0275(18) -0.0022(13) -0.0014(15) 0.0003(14) C18 0.0247(17) 0.0228(15) 0.0224(17) 0.0024(12) 0.0019(13) 0.0019(13) N4 0.0252(14) 0.0204(13) 0.0260(15) -0.0010(10) -0.0011(11) -0.0001(11) C19 0.0225(16) 0.0199(15) 0.0265(18) 0.0016(12) -0.0002(13) 0.0003(13) N5 0.0238(14) 0.0201(13) 0.0223(14) -0.0022(10) -0.0031(11) 0.0011(11) C20 0.0224(16) 0.0226(16) 0.0229(17) -0.0044(12) -0.0005(13) 0.0030(13) C21 0.032(2) 0.0224(16) 0.0263(19) -0.0005(14) -0.0020(14) -0.0014(14) C22 0.038(2) 0.042(2) 0.027(2) -0.0048(15) -0.0027(16) -0.0004(16) C23 0.034(2) 0.035(2) 0.037(2) -0.0186(16) -0.0002(16) 0.0019(16) C24 0.0303(19) 0.0203(17) 0.051(2) -0.0078(16) 0.0070(17) 0.0001(14) C25 0.0273(18) 0.0274(17) 0.0316(19) 0.0004(14) 0.0058(14) -0.0001(14) C26 0.0228(17) 0.0226(16) 0.0227(17) 0.0035(13) 0.0019(13) -0.0001(13) C27 0.0260(18) 0.0214(15) 0.0314(19) 0.0012(13) 0.0050(14) -0.0012(13) C28 0.0243(18) 0.0345(19) 0.033(2) 0.0097(15) -0.0005(15) 0.0033(14) C29 0.0256(18) 0.0359(19) 0.0264(18) 0.0056(15) -0.0033(14) -0.0021(15) C30 0.0333(19) 0.0262(17) 0.0219(17) -0.0028(13) 0.0040(14) -0.0011(14) C31 0.0229(17) 0.0218(15) 0.0206(17) 0.0016(13) 0.0004(13) -0.0007(13) Cl1 0.0256(4) 0.0268(4) 0.0481(5) 0.0035(4) -0.0033(4) -0.0021(3) Cl2 0.0401(5) 0.0494(5) 0.0242(5) 0.0106(4) 0.0044(4) 0.0129(4) _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 2.133(3) . ? Zn1 N1 2.139(3) . ? Zn1 N3 2.237(3) . ? Zn1 Cl1 2.2558(10) . ? Zn1 Cl2 2.2731(10) . ? N1 C13 1.318(4) . ? N1 C1 1.387(4) . ? C1 C2 1.396(4) . ? C1 C6 1.397(4) . ? C2 C3 1.367(5) . ? C2 H2 0.9500 . ? C3 C4 1.409(5) . ? C3 H3 0.9500 . ? C4 C5 1.373(5) . ? C4 H4 0.9500 . ? C5 C6 1.386(4) . ? C5 H5 0.9500 . ? C6 N2 1.405(4) . ? N2 C13 1.378(4) . ? N2 C7 1.442(4) . ? C7 C12 1.382(5) . ? C7 C8 1.391(4) . ? C8 C9 1.394(4) . ? C8 H8 0.9500 . ? C9 C10 1.385(6) . ? C9 H9 0.9500 . ? C10 C11 1.372(6) . ? C10 H10 0.9500 . ? C11 C12 1.400(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.485(4) . ? N3 C14 1.338(4) . ? N3 C18 1.340(4) . ? C14 C15 1.387(5) . ? C15 C16 1.391(5) . ? C15 H15 0.9500 . ? C16 C17 1.384(5) . ? C16 H16 0.9500 . ? C17 C18 1.391(4) . ? C17 H17 0.9500 . ? C18 C19 1.484(4) . ? N4 C19 1.321(4) . ? N4 C31 1.382(4) . ? C19 N5 1.367(4) . ? N5 C26 1.402(4) . ? N5 C20 1.440(4) . ? C20 C25 1.381(4) . ? C20 C21 1.382(5) . ? C21 C22 1.394(5) . ? C21 H21 0.9500 . ? C22 C23 1.374(5) . ? C22 H22 0.9500 . ? C23 C24 1.377(5) . ? C23 H23 0.9500 . ? C24 C25 1.388(5) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.392(4) . ? C26 C31 1.399(4) . ? C27 C28 1.381(5) . ? C27 H27 0.9500 . ? C28 C29 1.399(5) . ? C28 H28 0.9500 . ? C29 C30 1.373(4) . ? C29 H29 0.9500 . ? C30 C31 1.397(4) . ? C30 H30 0.9500 . ? 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 N1 144.52(10) . . ? N4 Zn1 N3 72.44(9) . . ? N1 Zn1 N3 72.10(9) . . ? N4 Zn1 Cl1 97.27(8) . . ? N1 Zn1 Cl1 98.35(8) . . ? N3 Zn1 Cl1 118.73(8) . . ? N4 Zn1 Cl2 100.17(8) . . ? N1 Zn1 Cl2 99.98(8) . . ? N3 Zn1 Cl2 122.79(8) . . ? Cl1 Zn1 Cl2 118.48(4) . . ? C13 N1 C1 106.9(2) . . ? C13 N1 Zn1 119.3(2) . . ? C1 N1 Zn1 133.0(2) . . ? N1 C1 C2 130.2(3) . . ? N1 C1 C6 108.8(3) . . ? C2 C1 C6 121.0(3) . . ? C3 C2 C1 117.2(3) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C2 C3 C4 121.2(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 122.3(3) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 C6 116.4(3) . . ? C4 C5 H5 121.8 . . ? C6 C5 H5 121.8 . . ? C5 C6 C1 121.9(3) . . ? C5 C6 N2 131.8(3) . . ? C1 C6 N2 106.3(3) . . ? C13 N2 C6 105.9(2) . . ? C13 N2 C7 130.3(3) . . ? C6 N2 C7 123.5(2) . . ? C12 C7 C8 122.0(3) . . ? C12 C7 N2 120.5(3) . . ? C8 C7 N2 117.4(3) . . ? C7 C8 C9 118.3(3) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C10 C9 C8 120.4(3) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.7(4) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C7 C12 C11 118.3(3) . . ? C7 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? N1 C13 N2 112.2(3) . . ? N1 C13 C14 117.8(3) . . ? N2 C13 C14 130.0(3) . . ? C14 N3 C18 120.8(3) . . ? C14 N3 Zn1 119.2(2) . . ? C18 N3 Zn1 118.8(2) . . ? N3 C14 C15 121.4(3) . . ? N3 C14 C13 110.0(3) . . ? C15 C14 C13 128.5(3) . . ? C14 C15 C16 117.6(3) . . ? C14 C15 H15 121.2 . . ? C16 C15 H15 121.2 . . ? C17 C16 C15 121.2(3) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 117.5(3) . . ? C16 C17 H17 121.2 . . ? C18 C17 H17 121.2 . . ? N3 C18 C17 121.4(3) . . ? N3 C18 C19 110.5(3) . . ? C17 C18 C19 128.0(3) . . ? C19 N4 C31 106.1(2) . . ? C19 N4 Zn1 119.3(2) . . ? C31 N4 Zn1 134.53(19) . . ? N4 C19 N5 112.7(3) . . ? N4 C19 C18 118.1(3) . . ? N5 C19 C18 129.2(3) . . ? C19 N5 C26 106.2(2) . . ? C19 N5 C20 131.0(2) . . ? C26 N5 C20 122.0(2) . . ? C25 C20 C21 121.3(3) . . ? C25 C20 N5 118.6(3) . . ? C21 C20 N5 119.9(3) . . ? C20 C21 C22 118.9(3) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C23 C22 C21 120.1(4) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 120.5(3) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C25 120.3(3) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C20 C25 C24 118.9(3) . . ? C20 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? C27 C26 C31 122.9(3) . . ? C27 C26 N5 131.4(3) . . ? C31 C26 N5 105.7(3) . . ? C28 C27 C26 115.7(3) . . ? C28 C27 H27 122.2 . . ? C26 C27 H27 122.2 . . ? C27 C28 C29 122.1(3) . . ? C27 C28 H28 118.9 . . ? C29 C28 H28 118.9 . . ? C30 C29 C28 121.9(3) . . ? C30 C29 H29 119.0 . . ? C28 C29 H29 119.0 . . ? C29 C30 C31 117.2(3) . . ? C29 C30 H30 121.4 . . ? C31 C30 H30 121.4 . . ? N4 C31 C30 130.4(3) . . ? N4 C31 C26 109.3(2) . . ? C30 C31 C26 120.2(3) . . ? 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 -0.4(3) . . . . ? N3 Zn1 N1 C13 1.9(2) . . . . ? Cl1 Zn1 N1 C13 -115.7(2) . . . . ? Cl2 Zn1 N1 C13 123.3(2) . . . . ? N4 Zn1 N1 C1 167.5(3) . . . . ? N3 Zn1 N1 C1 169.9(3) . . . . ? Cl1 Zn1 N1 C1 52.3(3) . . . . ? Cl2 Zn1 N1 C1 -68.7(3) . . . . ? C13 N1 C1 C2 178.3(4) . . . . ? Zn1 N1 C1 C2 9.2(5) . . . . ? C13 N1 C1 C6 -0.2(4) . . . . ? Zn1 N1 C1 C6 -169.2(2) . . . . ? N1 C1 C2 C3 -176.3(3) . . . . ? C6 C1 C2 C3 2.0(5) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C3 C4 C5 C6 0.7(5) . . . . ? C4 C5 C6 C1 0.6(5) . . . . ? C4 C5 C6 N2 176.4(3) . . . . ? N1 C1 C6 C5 176.6(3) . . . . ? C2 C1 C6 C5 -2.0(5) . . . . ? N1 C1 C6 N2 -0.1(4) . . . . ? C2 C1 C6 N2 -178.7(3) . . . . ? C5 C6 N2 C13 -175.9(3) . . . . ? C1 C6 N2 C13 0.3(3) . . . . ? C5 C6 N2 C7 -1.8(5) . . . . ? C1 C6 N2 C7 174.5(3) . . . . ? C13 N2 C7 C12 46.5(5) . . . . ? C6 N2 C7 C12 -126.1(3) . . . . ? C13 N2 C7 C8 -137.9(3) . . . . ? C6 N2 C7 C8 49.5(4) . . . . ? C12 C7 C8 C9 -0.8(5) . . . . ? N2 C7 C8 C9 -176.3(3) . . . . ? C7 C8 C9 C10 -1.4(5) . . . . ? C8 C9 C10 C11 1.7(5) . . . . ? C9 C10 C11 C12 0.2(6) . . . . ? C8 C7 C12 C11 2.6(5) . . . . ? N2 C7 C12 C11 178.0(3) . . . . ? C10 C11 C12 C7 -2.3(5) . . . . ? C1 N1 C13 N2 0.4(4) . . . . ? Zn1 N1 C13 N2 171.2(2) . . . . ? C1 N1 C13 C14 179.7(3) . . . . ? Zn1 N1 C13 C14 -9.4(4) . . . . ? C6 N2 C13 N1 -0.5(4) . . . . ? C7 N2 C13 N1 -174.1(3) . . . . ? C6 N2 C13 C14 -179.7(3) . . . . ? C7 N2 C13 C14 6.7(5) . . . . ? N4 Zn1 N3 C14 -174.8(3) . . . . ? N1 Zn1 N3 C14 6.6(2) . . . . ? Cl1 Zn1 N3 C14 96.5(2) . . . . ? Cl2 Zn1 N3 C14 -83.9(2) . . . . ? N4 Zn1 N3 C18 -7.3(2) . . . . ? N1 Zn1 N3 C18 174.2(3) . . . . ? Cl1 Zn1 N3 C18 -96.0(2) . . . . ? Cl2 Zn1 N3 C18 83.7(2) . . . . ? C18 N3 C14 C15 -2.5(5) . . . . ? Zn1 N3 C14 C15 164.8(3) . . . . ? C18 N3 C14 C13 -179.9(3) . . . . ? Zn1 N3 C14 C13 -12.6(4) . . . . ? N1 C13 C14 N3 14.2(4) . . . . ? N2 C13 C14 N3 -166.7(3) . . . . ? N1 C13 C14 C15 -163.0(3) . . . . ? N2 C13 C14 C15 16.2(6) . . . . ? N3 C14 C15 C16 1.8(5) . . . . ? C13 C14 C15 C16 178.7(3) . . . . ? C14 C15 C16 C17 0.4(5) . . . . ? C15 C16 C17 C18 -1.9(5) . . . . ? C14 N3 C18 C17 0.9(5) . . . . ? Zn1 N3 C18 C17 -166.5(3) . . . . ? C14 N3 C18 C19 177.5(3) . . . . ? Zn1 N3 C18 C19 10.2(3) . . . . ? C16 C17 C18 N3 1.3(5) . . . . ? C16 C17 C18 C19 -174.7(3) . . . . ? N1 Zn1 N4 C19 4.6(4) . . . . ? N3 Zn1 N4 C19 2.3(2) . . . . ? Cl1 Zn1 N4 C19 120.2(2) . . . . ? Cl2 Zn1 N4 C19 -119.1(2) . . . . ? N1 Zn1 N4 C31 -172.5(3) . . . . ? N3 Zn1 N4 C31 -174.9(3) . . . . ? Cl1 Zn1 N4 C31 -57.0(3) . . . . ? Cl2 Zn1 N4 C31 63.8(3) . . . . ? C31 N4 C19 N5 -1.1(4) . . . . ? Zn1 N4 C19 N5 -179.0(2) . . . . ? C31 N4 C19 C18 -179.8(3) . . . . ? Zn1 N4 C19 C18 2.3(4) . . . . ? N3 C18 C19 N4 -8.2(4) . . . . ? C17 C18 C19 N4 168.2(3) . . . . ? N3 C18 C19 N5 173.4(3) . . . . ? C17 C18 C19 N5 -10.2(6) . . . . ? N4 C19 N5 C26 0.3(4) . . . . ? C18 C19 N5 C26 178.8(3) . . . . ? N4 C19 N5 C20 169.6(3) . . . . ? C18 C19 N5 C20 -11.9(5) . . . . ? C19 N5 C20 C25 128.8(4) . . . . ? C26 N5 C20 C25 -63.3(4) . . . . ? C19 N5 C20 C21 -56.8(5) . . . . ? C26 N5 C20 C21 111.1(3) . . . . ? C25 C20 C21 C22 -1.0(5) . . . . ? N5 C20 C21 C22 -175.3(3) . . . . ? C20 C21 C22 C23 -0.1(5) . . . . ? C21 C22 C23 C24 0.6(6) . . . . ? C22 C23 C24 C25 -0.1(5) . . . . ? C21 C20 C25 C24 1.5(5) . . . . ? N5 C20 C25 C24 175.8(3) . . . . ? C23 C24 C25 C20 -0.9(5) . . . . ? C19 N5 C26 C27 179.5(3) . . . . ? C20 N5 C26 C27 9.1(5) . . . . ? C19 N5 C26 C31 0.7(3) . . . . ? C20 N5 C26 C31 -169.8(3) . . . . ? C31 C26 C27 C28 2.1(5) . . . . ? N5 C26 C27 C28 -176.6(3) . . . . ? C26 C27 C28 C29 1.0(5) . . . . ? C27 C28 C29 C30 -2.7(5) . . . . ? C28 C29 C30 C31 1.1(5) . . . . ? C19 N4 C31 C30 -174.7(3) . . . . ? Zn1 N4 C31 C30 2.7(6) . . . . ? C19 N4 C31 C26 1.5(4) . . . . ? Zn1 N4 C31 C26 178.9(2) . . . . ? C29 C30 C31 N4 177.8(3) . . . . ? C29 C30 C31 C26 1.9(5) . . . . ? C27 C26 C31 N4 179.7(3) . . . . ? N5 C26 C31 N4 -1.3(4) . . . . ? C27 C26 C31 C30 -3.7(5) . . . . ? N5 C26 C31 C30 175.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.275 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.062 data_full _database_code_depnum_ccdc_archive 'CCDC 874328' #TrackingRef 'complex 2.cif' _audit_creation_method SHELXL-97 #============================================================================= _chemical_name_systematic ; ethanol perchlorate bis[2,6-bis(1-pheny-1H-benzo[d]imidazo-2-yl)pyridine] zinc(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H42 N10 Zn, 2(Cl O4), C2 H6 O, 0.5(H4 O2)' _chemical_formula_sum 'C64 H50 Cl2 N10 O10 Zn' _chemical_formula_weight 1255.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 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 11.1528(10) _cell_length_b 13.9924(12) _cell_length_c 19.1852(17) _cell_angle_alpha 82.0960(10) _cell_angle_beta 76.3430(10) _cell_angle_gamma 89.2320(10) _cell_volume 2881.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.0 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.590 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.899 _exptl_absorpt_process_details 'SADABS (Bruker, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20988 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 25.01 _reflns_number_total 10170 _reflns_number_gt 7549 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1269P)^2^+9.7938P] 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 10069 _refine_ls_number_parameters 804 _refine_ls_number_restraints 53 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.2349 _refine_ls_wR_factor_gt 0.2068 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.117 _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 0.50590(5) 0.51124(4) 0.73257(3) 0.0243(2) Uani 1 1 d . . . N1 N 0.5613(4) 0.5423(3) 0.8270(2) 0.0263(9) Uani 1 1 d . . . N2 N 0.6513(4) 0.6478(3) 0.8761(2) 0.0281(10) Uani 1 1 d . . . N3 N 0.5320(4) 0.6631(3) 0.7152(2) 0.0246(9) Uani 1 1 d . . . N4 N 0.4566(4) 0.5569(3) 0.6304(2) 0.0246(9) Uani 1 1 d . . . N5 N 0.3859(4) 0.6783(3) 0.5636(2) 0.0271(9) Uani 1 1 d . . . N6 N 0.6758(4) 0.4382(3) 0.7000(2) 0.0263(9) Uani 1 1 d . . . N7 N 0.7727(4) 0.2991(3) 0.6873(2) 0.0286(10) Uani 1 1 d . . . N8 N 0.4537(4) 0.3618(3) 0.7455(2) 0.0259(9) Uani 1 1 d . . . N9 N 0.3083(4) 0.5043(3) 0.7849(2) 0.0264(9) Uani 1 1 d . . . N10 N 0.1434(4) 0.4106(3) 0.8409(2) 0.0289(10) Uani 1 1 d . . . C1 C 0.5846(5) 0.3956(4) 0.9142(3) 0.0335(12) Uani 1 1 d . . . H1A H 0.5469 0.3506 0.8928 0.040 Uiso 1 1 calc R . . C2 C 0.6290(5) 0.3669(5) 0.9752(3) 0.0392(14) Uani 1 1 d . . . H2A H 0.6218 0.3009 0.9959 0.047 Uiso 1 1 calc R . . C3 C 0.6841(6) 0.4329(5) 1.0068(3) 0.0410(15) Uani 1 1 d . . . H3A H 0.7136 0.4105 1.0486 0.049 Uiso 1 1 calc R . . C4 C 0.6971(5) 0.5299(5) 0.9793(3) 0.0366(13) Uani 1 1 d . . . H4A H 0.7344 0.5748 1.0010 0.044 Uiso 1 1 calc R . . C5 C 0.6522(5) 0.5578(4) 0.9176(3) 0.0292(12) Uani 1 1 d . . . C6 C 0.5973(5) 0.4931(4) 0.8854(3) 0.0278(11) Uani 1 1 d . . . C8 C 0.7209(5) 0.7319(4) 0.8812(3) 0.0329(12) Uani 1 1 d . . . C9 C 0.6835(6) 0.7805(5) 0.9406(4) 0.0455(15) Uani 1 1 d . . . H9A H 0.6119 0.7603 0.9775 0.055 Uiso 1 1 calc R . . C10 C 0.7541(8) 0.8597(5) 0.9446(4) 0.058(2) Uani 1 1 d . . . H10A H 0.7306 0.8941 0.9849 0.070 Uiso 1 1 calc R . . C11 C 0.8571(8) 0.8889(5) 0.8912(5) 0.057(2) Uani 1 1 d . . . H11A H 0.9048 0.9430 0.8947 0.069 Uiso 1 1 calc R . . C12 C 0.8913(6) 0.8398(5) 0.8324(4) 0.0498(17) Uani 1 1 d . . . H12A H 0.9622 0.8608 0.7953 0.060 Uiso 1 1 calc R . . C13 C 0.8238(5) 0.7604(4) 0.8266(3) 0.0379(13) Uani 1 1 d . . . H13A H 0.8478 0.7263 0.7862 0.046 Uiso 1 1 calc R . . C14 C 0.5957(5) 0.6330(4) 0.8224(3) 0.0254(11) Uani 1 1 d . . . C15 C 0.5684(4) 0.7050(4) 0.7651(3) 0.0253(11) Uani 1 1 d . . . C16 C 0.5662(5) 0.8050(4) 0.7635(3) 0.0318(12) Uani 1 1 d . . . H16A H 0.5915 0.8350 0.7993 0.038 Uiso 1 1 calc R . . C17 C 0.5255(5) 0.8591(4) 0.7074(3) 0.0338(12) Uani 1 1 d . . . H17A H 0.5243 0.9274 0.7041 0.041 Uiso 1 1 calc R . . C18 C 0.4868(5) 0.8146(4) 0.6565(3) 0.0303(12) Uani 1 1 d . . . H18A H 0.4573 0.8516 0.6189 0.036 Uiso 1 1 calc R . . C19 C 0.4917(4) 0.7153(4) 0.6612(3) 0.0243(10) Uani 1 1 d . . . C20 C 0.4481(5) 0.6514(4) 0.6163(3) 0.0246(11) Uani 1 1 d . . . C22 C 0.3660(5) 0.7745(4) 0.5303(3) 0.0292(12) Uani 1 1 d . . . C23 C 0.4646(5) 0.8250(4) 0.4835(3) 0.0327(12) Uani 1 1 d . . . H23A H 0.5432 0.7963 0.4720 0.039 Uiso 1 1 calc R . . C24 C 0.4471(6) 0.9187(4) 0.4533(3) 0.0387(14) Uani 1 1 d . . . H24A H 0.5144 0.9549 0.4215 0.046 Uiso 1 1 calc R . . C25 C 0.3323(6) 0.9591(4) 0.4695(4) 0.0447(15) Uani 1 1 d . . . H25A H 0.3206 1.0233 0.4490 0.054 Uiso 1 1 calc R . . C26 C 0.2346(6) 0.9065(5) 0.5153(4) 0.0498(17) Uani 1 1 d . . . H26A H 0.1553 0.9343 0.5257 0.060 Uiso 1 1 calc R . . C27 C 0.2507(5) 0.8131(4) 0.5464(3) 0.0402(14) Uani 1 1 d . . . H27A H 0.1834 0.7768 0.5781 0.048 Uiso 1 1 calc R . . C28 C 0.3495(5) 0.5938(4) 0.5436(3) 0.0270(11) Uani 1 1 d . . . C29 C 0.2797(5) 0.5774(4) 0.4948(3) 0.0336(12) Uani 1 1 d . . . H29A H 0.2474 0.6289 0.4675 0.040 Uiso 1 1 calc R . . C30 C 0.2599(5) 0.4819(4) 0.4883(3) 0.0355(13) Uani 1 1 d . . . H30A H 0.2118 0.4677 0.4561 0.043 Uiso 1 1 calc R . . C31 C 0.3082(5) 0.4061(4) 0.5274(3) 0.0331(12) Uani 1 1 d . . . H31A H 0.2929 0.3416 0.5209 0.040 Uiso 1 1 calc R . . C32 C 0.3784(5) 0.4225(4) 0.5755(3) 0.0296(11) Uani 1 1 d . . . H32A H 0.4123 0.3706 0.6016 0.035 Uiso 1 1 calc R . . C33 C 0.3973(4) 0.5188(4) 0.5844(3) 0.0253(11) Uani 1 1 d . . . C34 C 0.2231(5) 0.6585(4) 0.8301(3) 0.0311(12) Uani 1 1 d . . . H34A H 0.2913 0.6993 0.8046 0.037 Uiso 1 1 calc R . . C35 C 0.1231(5) 0.6936(4) 0.8762(3) 0.0361(13) Uani 1 1 d . . . H35A H 0.1231 0.7595 0.8831 0.043 Uiso 1 1 calc R . . C36 C 0.0217(5) 0.6339(4) 0.9129(3) 0.0381(13) Uani 1 1 d . . . H36A H -0.0454 0.6604 0.9443 0.046 Uiso 1 1 calc R . . C37 C 0.0162(5) 0.5387(4) 0.9049(3) 0.0349(13) Uani 1 1 d . . . H37A H -0.0530 0.4986 0.9299 0.042 Uiso 1 1 calc R . . C38 C 0.1172(5) 0.5031(4) 0.8583(3) 0.0306(12) Uani 1 1 d . . . C39 C 0.2204(5) 0.5604(4) 0.8223(3) 0.0262(11) Uani 1 1 d . . . C41 C 0.0656(5) 0.3272(4) 0.8690(3) 0.0314(12) Uani 1 1 d . . . C42 C -0.0524(5) 0.3272(5) 0.8554(3) 0.0407(14) Uani 1 1 d . . . H42A H -0.0800 0.3808 0.8277 0.049 Uiso 1 1 calc R . . C43 C -0.1273(6) 0.2463(5) 0.8840(4) 0.0523(18) Uani 1 1 d . . . H43A H -0.2081 0.2449 0.8760 0.063 Uiso 1 1 calc R . . C44 C -0.0879(7) 0.1683(5) 0.9233(4) 0.060(2) Uani 1 1 d . . . H44A H -0.1407 0.1135 0.9420 0.072 Uiso 1 1 calc R . . C45 C 0.0294(8) 0.1696(5) 0.9357(4) 0.0567(19) Uani 1 1 d . . . H45A H 0.0569 0.1154 0.9630 0.068 Uiso 1 1 calc R . . C46 C 0.1068(6) 0.2495(4) 0.9087(3) 0.0421(14) Uani 1 1 d . . . H46A H 0.1871 0.2506 0.9174 0.051 Uiso 1 1 calc R . . C47 C 0.2599(5) 0.4167(4) 0.7966(3) 0.0281(11) Uani 1 1 d . . . C48 C 0.3335(5) 0.3378(4) 0.7648(3) 0.0290(11) Uani 1 1 d . . . C49 C 0.2918(6) 0.2508(4) 0.7513(4) 0.0443(15) Uani 1 1 d . . . H49A H 0.2065 0.2336 0.7648 0.053 Uiso 1 1 calc R . . C50 C 0.3787(6) 0.1897(5) 0.7175(4) 0.0470(16) Uani 1 1 d . . . H50A H 0.3524 0.1302 0.7067 0.056 Uiso 1 1 calc R . . C51 C 0.5026(5) 0.2140(4) 0.6994(3) 0.0358(13) Uani 1 1 d . . . H51A H 0.5625 0.1718 0.6770 0.043 Uiso 1 1 calc R . . C52 C 0.5367(5) 0.3023(4) 0.7149(3) 0.0273(11) Uani 1 1 d . . . C53 C 0.6623(5) 0.3449(4) 0.6998(3) 0.0255(11) Uani 1 1 d . . . C55 C 0.7929(5) 0.1971(4) 0.6896(3) 0.0284(11) Uani 1 1 d . . . C56 C 0.7381(5) 0.1357(4) 0.7514(3) 0.0343(12) Uani 1 1 d . . . H56A H 0.6915 0.1607 0.7929 0.041 Uiso 1 1 calc R . . C57 C 0.7522(6) 0.0374(4) 0.7521(3) 0.0412(14) Uani 1 1 d . . . H57A H 0.7131 -0.0057 0.7938 0.049 Uiso 1 1 calc R . . C58 C 0.8229(6) 0.0018(4) 0.6925(4) 0.0450(15) Uani 1 1 d . . . H58A H 0.8326 -0.0659 0.6932 0.054 Uiso 1 1 calc R . . C59 C 0.8793(6) 0.0639(5) 0.6321(3) 0.0440(15) Uani 1 1 d . . . H59A H 0.9289 0.0387 0.5915 0.053 Uiso 1 1 calc R . . C60 C 0.8648(5) 0.1627(4) 0.6295(3) 0.0364(13) Uani 1 1 d . . . H60A H 0.9032 0.2056 0.5876 0.044 Uiso 1 1 calc R . . C61 C 0.8634(5) 0.3702(4) 0.6798(3) 0.0289(11) Uani 1 1 d . . . C62 C 0.9909(5) 0.3654(4) 0.6675(3) 0.0384(14) Uani 1 1 d . . . H62A H 1.0334 0.3069 0.6606 0.046 Uiso 1 1 calc R . . C63 C 1.0528(5) 0.4516(5) 0.6659(3) 0.0435(15) Uani 1 1 d . . . H63A H 1.1400 0.4519 0.6590 0.052 Uiso 1 1 calc R . . C64 C 0.9899(6) 0.5378(5) 0.6741(3) 0.0425(14) Uani 1 1 d . . . H64A H 1.0359 0.5951 0.6723 0.051 Uiso 1 1 calc R . . C65 C 0.8644(5) 0.5429(4) 0.6847(3) 0.0351(13) Uani 1 1 d . . . H65A H 0.8229 0.6022 0.6894 0.042 Uiso 1 1 calc R . . C66 C 0.7998(5) 0.4563(4) 0.6883(3) 0.0267(11) Uani 1 1 d . . . O5 O 0.6371(8) 1.1541(5) 1.0903(5) 0.143(4) Uani 1 1 d D . . Cl1 Cl 0.11433(16) 1.21555(12) 0.43218(10) 0.0575(5) Uani 1 1 d D . . Cl2 Cl 0.6536(3) 1.05934(18) 1.1065(2) 0.1476(18) Uani 1 1 d D . . O1 O 0.0882(6) 1.1211(3) 0.4697(3) 0.0834(19) Uani 1 1 d D . . O2 O 0.0444(5) 1.2846(3) 0.4717(3) 0.0716(16) Uani 1 1 d D . . O3 O 0.0741(8) 1.2180(5) 0.3644(3) 0.111(3) Uani 1 1 d D . . O4 O 0.2393(5) 1.2416(6) 0.4147(5) 0.129(3) Uani 1 1 d D . . O6 O 0.5602(7) 1.0037(5) 1.1577(4) 0.126(3) Uani 1 1 d D . . O7 O 0.7476(7) 1.0061(6) 1.0727(4) 0.117(3) Uani 1 1 d D . . O8 O 0.7258(16) 1.0890(13) 1.1628(8) 0.312(10) Uani 1 1 d DU . . O9 O 0.2763(12) -0.0175(8) 0.6829(7) 0.173(4) Uani 1 1 d DU B . H9 H 0.2748 -0.0383 0.7269 0.259 Uiso 1 1 d R . . C67 C 0.1629(15) 0.0387(14) 0.6741(9) 0.212(9) Uani 1 1 d DU . . H67A H 0.1246 0.0647 0.7195 0.254 Uiso 1 1 calc R A 1 H67B H 0.1017 -0.0041 0.6633 0.254 Uiso 1 1 calc R A 1 C681 C 0.2019(14) 0.1232(13) 0.6108(9) 0.081(6) Uani 0.50 1 d PD B 1 H68A H 0.2918 0.1244 0.5928 0.122 Uiso 0.50 1 calc PR B 1 H68B H 0.1757 0.1846 0.6283 0.122 Uiso 0.50 1 calc PR B 1 H68C H 0.1627 0.1139 0.5715 0.122 Uiso 0.50 1 calc PR B 1 C682 C 0.1034(17) 0.056(2) 0.7514(12) 0.153(15) Uani 0.50 1 d PD B 2 H68D H 0.1461 0.0184 0.7849 0.230 Uiso 0.50 1 calc PR B 2 H68E H 0.0163 0.0354 0.7636 0.230 Uiso 0.50 1 calc PR B 2 H68F H 0.1094 0.1246 0.7553 0.230 Uiso 0.50 1 calc PR B 2 O2W O 0.4885(15) 1.1766(9) 0.8944(7) 0.106(4) Uani 0.50 1 d PU C 1 H201 H 0.5280 1.1501 0.9246 0.159 Uiso 0.50 1 d PR C 1 H202 H 0.4589 1.1332 0.8764 0.159 Uiso 0.50 1 d PR C 1 O1W O 0.5934(15) 1.1127(12) 0.9406(10) 0.123(5) Uani 0.50 1 d PU D 2 H101 H 0.6249 1.1574 0.9560 0.184 Uiso 0.50 1 d PR D 2 H102 H 0.5578 1.0744 0.9769 0.184 Uiso 0.50 1 d PR D 2 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 0.0248(3) 0.0225(3) 0.0265(3) -0.0041(2) -0.0074(2) 0.0028(2) N1 0.028(2) 0.027(2) 0.026(2) -0.0053(18) -0.0082(18) 0.0049(18) N2 0.030(2) 0.031(2) 0.025(2) -0.0034(18) -0.0110(19) 0.0033(19) N3 0.025(2) 0.026(2) 0.023(2) -0.0046(17) -0.0065(17) 0.0012(17) N4 0.024(2) 0.028(2) 0.022(2) -0.0042(17) -0.0061(17) 0.0008(17) N5 0.029(2) 0.029(2) 0.024(2) -0.0017(18) -0.0083(18) 0.0008(18) N6 0.024(2) 0.026(2) 0.029(2) -0.0059(18) -0.0048(18) 0.0034(17) N7 0.028(2) 0.029(2) 0.027(2) -0.0036(18) -0.0039(19) 0.0037(18) N8 0.027(2) 0.026(2) 0.024(2) -0.0061(18) -0.0044(18) 0.0027(18) N9 0.023(2) 0.030(2) 0.028(2) -0.0075(18) -0.0068(18) 0.0017(18) N10 0.024(2) 0.031(2) 0.030(2) -0.0051(19) -0.0034(18) 0.0006(18) C1 0.032(3) 0.034(3) 0.033(3) -0.001(2) -0.006(2) 0.004(2) C2 0.036(3) 0.041(3) 0.033(3) 0.009(3) -0.002(3) 0.009(3) C3 0.039(3) 0.054(4) 0.026(3) 0.005(3) -0.007(3) 0.015(3) C4 0.031(3) 0.051(4) 0.028(3) -0.006(3) -0.008(2) 0.005(3) C5 0.026(3) 0.034(3) 0.027(3) -0.005(2) -0.005(2) 0.006(2) C6 0.025(3) 0.033(3) 0.023(3) -0.002(2) -0.002(2) 0.008(2) C8 0.037(3) 0.035(3) 0.031(3) -0.007(2) -0.017(2) 0.008(2) C9 0.053(4) 0.047(4) 0.047(4) -0.019(3) -0.024(3) 0.007(3) C10 0.085(6) 0.045(4) 0.062(5) -0.027(4) -0.042(4) 0.013(4) C11 0.078(5) 0.032(3) 0.077(5) -0.004(3) -0.050(5) -0.005(3) C12 0.049(4) 0.042(4) 0.059(4) 0.008(3) -0.023(3) -0.006(3) C13 0.040(3) 0.036(3) 0.038(3) -0.001(3) -0.014(3) 0.000(3) C14 0.025(3) 0.026(3) 0.027(3) -0.006(2) -0.009(2) 0.004(2) C15 0.022(2) 0.028(3) 0.026(3) -0.005(2) -0.006(2) 0.003(2) C16 0.038(3) 0.028(3) 0.034(3) -0.009(2) -0.014(2) 0.004(2) C17 0.043(3) 0.022(3) 0.039(3) -0.006(2) -0.014(3) 0.003(2) C18 0.037(3) 0.027(3) 0.029(3) 0.000(2) -0.014(2) 0.005(2) C19 0.021(2) 0.026(3) 0.025(3) 0.000(2) -0.006(2) 0.002(2) C20 0.025(3) 0.029(3) 0.020(2) -0.002(2) -0.006(2) 0.002(2) C22 0.038(3) 0.030(3) 0.024(3) -0.004(2) -0.015(2) 0.003(2) C23 0.036(3) 0.036(3) 0.026(3) -0.006(2) -0.006(2) 0.000(2) C24 0.054(4) 0.035(3) 0.028(3) 0.003(2) -0.013(3) -0.006(3) C25 0.057(4) 0.032(3) 0.047(4) 0.005(3) -0.023(3) 0.003(3) C26 0.044(4) 0.047(4) 0.063(4) -0.002(3) -0.025(3) 0.012(3) C27 0.031(3) 0.041(3) 0.048(4) 0.001(3) -0.011(3) 0.004(3) C28 0.027(3) 0.032(3) 0.021(2) -0.004(2) -0.006(2) 0.002(2) C29 0.037(3) 0.041(3) 0.026(3) -0.002(2) -0.014(2) 0.002(2) C30 0.034(3) 0.049(3) 0.027(3) -0.010(3) -0.012(2) -0.005(3) C31 0.030(3) 0.039(3) 0.032(3) -0.012(2) -0.006(2) -0.002(2) C32 0.027(3) 0.034(3) 0.027(3) -0.006(2) -0.005(2) 0.003(2) C33 0.020(2) 0.033(3) 0.023(2) -0.007(2) -0.002(2) 0.002(2) C34 0.029(3) 0.030(3) 0.035(3) 0.001(2) -0.012(2) 0.005(2) C35 0.040(3) 0.030(3) 0.038(3) -0.003(2) -0.010(3) 0.013(2) C36 0.034(3) 0.043(3) 0.036(3) -0.009(3) -0.002(3) 0.013(3) C37 0.027(3) 0.041(3) 0.035(3) -0.004(3) -0.004(2) 0.006(2) C38 0.030(3) 0.034(3) 0.030(3) -0.005(2) -0.011(2) 0.005(2) C39 0.024(3) 0.031(3) 0.025(3) -0.002(2) -0.010(2) 0.006(2) C41 0.027(3) 0.034(3) 0.033(3) -0.009(2) -0.001(2) -0.004(2) C42 0.033(3) 0.047(4) 0.044(3) -0.017(3) -0.006(3) 0.001(3) C43 0.031(3) 0.056(4) 0.069(5) -0.027(4) 0.001(3) -0.011(3) C44 0.056(4) 0.050(4) 0.062(5) -0.019(4) 0.016(4) -0.020(4) C45 0.077(5) 0.039(4) 0.050(4) 0.000(3) -0.009(4) -0.010(3) C46 0.044(3) 0.037(3) 0.046(4) -0.002(3) -0.015(3) -0.005(3) C47 0.025(3) 0.033(3) 0.028(3) -0.005(2) -0.009(2) 0.001(2) C48 0.024(3) 0.031(3) 0.031(3) -0.006(2) -0.006(2) 0.000(2) C49 0.033(3) 0.040(3) 0.061(4) -0.021(3) -0.005(3) -0.006(3) C50 0.040(3) 0.038(3) 0.071(5) -0.028(3) -0.017(3) -0.001(3) C51 0.034(3) 0.032(3) 0.045(3) -0.018(3) -0.011(3) 0.007(2) C52 0.028(3) 0.028(3) 0.027(3) -0.005(2) -0.008(2) 0.005(2) C53 0.028(3) 0.026(3) 0.022(2) -0.005(2) -0.004(2) 0.006(2) C55 0.028(3) 0.026(3) 0.031(3) -0.003(2) -0.007(2) 0.007(2) C56 0.033(3) 0.038(3) 0.031(3) -0.006(2) -0.006(2) 0.004(2) C57 0.045(3) 0.034(3) 0.042(3) 0.007(3) -0.013(3) 0.000(3) C58 0.055(4) 0.028(3) 0.055(4) -0.007(3) -0.019(3) 0.009(3) C59 0.051(4) 0.042(3) 0.040(3) -0.014(3) -0.010(3) 0.016(3) C60 0.039(3) 0.032(3) 0.036(3) -0.002(2) -0.004(3) 0.009(2) C61 0.031(3) 0.031(3) 0.023(3) -0.001(2) -0.005(2) 0.003(2) C62 0.029(3) 0.042(3) 0.041(3) -0.006(3) -0.003(3) 0.011(3) C63 0.025(3) 0.057(4) 0.045(4) -0.002(3) -0.002(3) -0.003(3) C64 0.035(3) 0.041(3) 0.048(4) -0.004(3) -0.005(3) -0.008(3) C65 0.035(3) 0.029(3) 0.038(3) -0.001(2) -0.005(3) -0.002(2) C66 0.027(3) 0.029(3) 0.022(2) -0.002(2) -0.003(2) 0.002(2) O5 0.127(7) 0.117(7) 0.138(7) 0.050(6) 0.020(6) 0.016(5) Cl1 0.0512(10) 0.0410(9) 0.0684(12) -0.0132(8) 0.0133(8) -0.0067(7) Cl2 0.130(2) 0.0537(14) 0.201(4) -0.0565(19) 0.100(3) -0.0356(15) O1 0.092(4) 0.048(3) 0.089(4) 0.011(3) 0.009(3) 0.012(3) O2 0.091(4) 0.045(3) 0.063(3) -0.011(2) 0.014(3) 0.010(3) O3 0.184(8) 0.086(5) 0.076(4) -0.029(4) -0.050(5) 0.017(5) O4 0.054(4) 0.140(7) 0.178(8) -0.057(6) 0.025(5) -0.020(4) O6 0.140(7) 0.083(5) 0.124(6) -0.042(5) 0.047(5) -0.047(5) O7 0.133(7) 0.114(6) 0.103(6) -0.045(5) -0.010(5) 0.033(5) O8 0.326(13) 0.290(13) 0.318(13) -0.063(10) -0.056(10) -0.030(10) O9 0.186(8) 0.147(7) 0.202(9) -0.056(7) -0.063(7) 0.028(6) C67 0.180(11) 0.256(13) 0.233(12) -0.054(10) -0.105(10) -0.001(9) C681 0.052(9) 0.119(16) 0.101(14) -0.064(13) -0.045(10) 0.028(10) C682 0.062(12) 0.27(3) 0.125(18) -0.14(2) 0.056(12) -0.109(17) O2W 0.155(9) 0.071(6) 0.065(6) -0.047(5) 0.055(6) -0.073(6) O1W 0.104(8) 0.116(9) 0.140(9) -0.056(8) 0.010(7) -0.053(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 Zn1 N3 2.118(4) . ? Zn1 N6 2.142(4) . ? Zn1 N8 2.143(4) . ? Zn1 N1 2.145(4) . ? Zn1 N4 2.169(4) . ? Zn1 N9 2.193(4) . ? N1 C14 1.316(6) . ? N1 C6 1.372(7) . ? N2 C14 1.362(6) . ? N2 C5 1.395(7) . ? N2 C8 1.444(7) . ? N3 C15 1.330(7) . ? N3 C19 1.346(6) . ? N4 C20 1.321(6) . ? N4 C33 1.384(6) . ? N5 C20 1.366(6) . ? N5 C28 1.385(7) . ? N5 C22 1.447(7) . ? N6 C53 1.317(7) . ? N6 C66 1.369(7) . ? N7 C53 1.365(6) . ? N7 C61 1.397(7) . ? N7 C55 1.438(7) . ? N8 C52 1.324(6) . ? N8 C48 1.339(7) . ? N9 C47 1.316(7) . ? N9 C39 1.376(6) . ? N10 C47 1.371(7) . ? N10 C38 1.391(7) . ? N10 C41 1.429(7) . ? C1 C2 1.384(8) . ? C1 C6 1.396(8) . ? C1 H1A 0.9500 . ? C2 C3 1.394(9) . ? C2 H2A 0.9500 . ? C3 C4 1.384(9) . ? C3 H3A 0.9500 . ? C4 C5 1.397(8) . ? C4 H4A 0.9500 . ? C5 C6 1.387(8) . ? C8 C13 1.379(8) . ? C8 C9 1.386(8) . ? C9 C10 1.389(10) . ? C9 H9A 0.9500 . ? C10 C11 1.371(12) . ? C10 H10A 0.9500 . ? C11 C12 1.375(11) . ? C11 H11A 0.9500 . ? C12 C13 1.382(9) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.471(7) . ? C15 C16 1.395(7) . ? C16 C17 1.391(8) . ? C16 H16A 0.9500 . ? C17 C18 1.378(8) . ? C17 H17A 0.9500 . ? C18 C19 1.381(7) . ? C18 H18A 0.9500 . ? C19 C20 1.482(7) . ? C22 C27 1.371(8) . ? C22 C23 1.376(8) . ? C23 C24 1.388(8) . ? C23 H23A 0.9500 . ? C24 C25 1.377(9) . ? C24 H24A 0.9500 . ? C25 C26 1.376(10) . ? C25 H25A 0.9500 . ? C26 C27 1.387(9) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C28 C29 1.395(7) . ? C28 C33 1.398(7) . ? C29 C30 1.384(8) . ? C29 H29A 0.9500 . ? C30 C31 1.391(8) . ? C30 H30A 0.9500 . ? C31 C32 1.387(8) . ? C31 H31A 0.9500 . ? C32 C33 1.406(7) . ? C32 H32A 0.9500 . ? C34 C35 1.380(8) . ? C34 C39 1.403(7) . ? C34 H34A 0.9500 . ? C35 C36 1.400(9) . ? C35 H35A 0.9500 . ? C36 C37 1.365(8) . ? C36 H36A 0.9500 . ? C37 C38 1.396(8) . ? C37 H37A 0.9500 . ? C38 C39 1.393(8) . ? C41 C46 1.378(8) . ? C41 C42 1.400(8) . ? C42 C43 1.386(9) . ? C42 H42A 0.9500 . ? C43 C44 1.367(11) . ? C43 H43A 0.9500 . ? C44 C45 1.385(11) . ? C44 H44A 0.9500 . ? C45 C46 1.385(9) . ? C45 H45A 0.9500 . ? C46 H46A 0.9500 . ? C47 C48 1.480(7) . ? C48 C49 1.387(8) . ? C49 C50 1.387(9) . ? C49 H49A 0.9500 . ? C50 C51 1.378(8) . ? C50 H50A 0.9500 . ? C51 C52 1.388(8) . ? C51 H51A 0.9500 . ? C52 C53 1.478(7) . ? C55 C60 1.382(8) . ? C55 C56 1.383(8) . ? C56 C57 1.380(8) . ? C56 H56A 0.9500 . ? C57 C58 1.377(9) . ? C57 H57A 0.9500 . ? C58 C59 1.375(9) . ? C58 H58A 0.9500 . ? C59 C60 1.385(8) . ? C59 H59A 0.9500 . ? C60 H60A 0.9500 . ? C61 C62 1.388(8) . ? C61 C66 1.400(7) . ? C62 C63 1.391(9) . ? C62 H62A 0.9500 . ? C63 C64 1.396(9) . ? C63 H63A 0.9500 . ? C64 C65 1.369(8) . ? C64 H64A 0.9500 . ? C65 C66 1.403(8) . ? C65 H65A 0.9500 . ? O5 Cl2 1.340(6) . ? Cl1 O4 1.395(6) . ? Cl1 O1 1.413(5) . ? Cl1 O2 1.421(4) . ? Cl1 O3 1.469(6) . ? Cl2 O7 1.366(6) . ? Cl2 O6 1.408(6) . ? Cl2 O8 1.591(9) . ? O9 C67 1.511(10) . ? O9 H9 0.8502 . ? C67 C682 1.524(10) . ? C67 C681 1.560(10) . ? C67 H67A 0.9900 . ? C67 H67B 0.9900 . ? C681 H68A 0.9800 . ? C681 H68B 0.9800 . ? C681 H68C 0.9800 . ? C682 H68D 0.9800 . ? C682 H68E 0.9800 . ? C682 H68F 0.9800 . ? O2W H201 0.8510 . ? O2W H202 0.8452 . ? O1W H201 0.9758 . ? O1W H101 0.8420 . ? O1W H102 0.8372 . ? 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 Zn1 N6 111.86(16) . . ? N3 Zn1 N8 171.37(16) . . ? N6 Zn1 N8 75.17(16) . . ? N3 Zn1 N1 75.94(16) . . ? N6 Zn1 N1 89.69(16) . . ? N8 Zn1 N1 109.79(16) . . ? N3 Zn1 N4 75.60(16) . . ? N6 Zn1 N4 102.69(16) . . ? N8 Zn1 N4 98.28(16) . . ? N1 Zn1 N4 151.46(16) . . ? N3 Zn1 N9 98.72(16) . . ? N6 Zn1 N9 149.20(16) . . ? N8 Zn1 N9 74.74(16) . . ? N1 Zn1 N9 94.38(16) . . ? N4 Zn1 N9 87.97(16) . . ? C14 N1 C6 106.6(4) . . ? C14 N1 Zn1 113.0(3) . . ? C6 N1 Zn1 138.5(4) . . ? C14 N2 C5 105.8(4) . . ? C14 N2 C8 127.9(4) . . ? C5 N2 C8 124.8(4) . . ? C15 N3 C19 121.4(4) . . ? C15 N3 Zn1 118.6(3) . . ? C19 N3 Zn1 119.1(3) . . ? C20 N4 C33 105.7(4) . . ? C20 N4 Zn1 112.9(3) . . ? C33 N4 Zn1 138.2(3) . . ? C20 N5 C28 106.6(4) . . ? C20 N5 C22 128.5(4) . . ? C28 N5 C22 124.9(4) . . ? C53 N6 C66 106.6(4) . . ? C53 N6 Zn1 114.2(3) . . ? C66 N6 Zn1 138.5(3) . . ? C53 N7 C61 106.2(4) . . ? C53 N7 C55 127.6(4) . . ? C61 N7 C55 125.8(4) . . ? C52 N8 C48 121.1(5) . . ? C52 N8 Zn1 117.6(3) . . ? C48 N8 Zn1 118.5(3) . . ? C47 N9 C39 106.1(4) . . ? C47 N9 Zn1 113.6(3) . . ? C39 N9 Zn1 139.0(3) . . ? C47 N10 C38 105.7(4) . . ? C47 N10 C41 128.7(5) . . ? C38 N10 C41 125.4(4) . . ? C2 C1 C6 117.5(6) . . ? C2 C1 H1A 121.2 . . ? C6 C1 H1A 121.2 . . ? C1 C2 C3 121.3(6) . . ? C1 C2 H2A 119.4 . . ? C3 C2 H2A 119.4 . . ? C4 C3 C2 122.1(5) . . ? C4 C3 H3A 119.0 . . ? C2 C3 H3A 119.0 . . ? C3 C4 C5 116.0(6) . . ? C3 C4 H4A 122.0 . . ? C5 C4 H4A 122.0 . . ? C6 C5 N2 106.3(4) . . ? C6 C5 C4 122.7(5) . . ? N2 C5 C4 131.0(5) . . ? N1 C6 C5 108.9(5) . . ? N1 C6 C1 130.7(5) . . ? C5 C6 C1 120.4(5) . . ? C13 C8 C9 122.1(6) . . ? C13 C8 N2 118.5(5) . . ? C9 C8 N2 119.4(5) . . ? C8 C9 C10 117.9(7) . . ? C8 C9 H9A 121.1 . . ? C10 C9 H9A 121.1 . . ? C11 C10 C9 121.0(7) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 119.9(6) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C11 C12 C13 120.9(7) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C8 C13 C12 118.3(6) . . ? C8 C13 H13A 120.9 . . ? C12 C13 H13A 120.9 . . ? N1 C14 N2 112.3(4) . . ? N1 C14 C15 119.8(4) . . ? N2 C14 C15 127.9(5) . . ? N3 C15 C16 121.2(5) . . ? N3 C15 C14 111.3(4) . . ? C16 C15 C14 127.1(5) . . ? C17 C16 C15 117.4(5) . . ? C17 C16 H16A 121.3 . . ? C15 C16 H16A 121.3 . . ? C18 C17 C16 120.7(5) . . ? C18 C17 H17A 119.6 . . ? C16 C17 H17A 119.6 . . ? C17 C18 C19 118.8(5) . . ? C17 C18 H18A 120.6 . . ? C19 C18 H18A 120.6 . . ? N3 C19 C18 120.4(5) . . ? N3 C19 C20 110.8(4) . . ? C18 C19 C20 128.6(5) . . ? N4 C20 N5 112.6(4) . . ? N4 C20 C19 120.2(4) . . ? N5 C20 C19 126.9(4) . . ? C27 C22 C23 121.9(5) . . ? C27 C22 N5 119.5(5) . . ? C23 C22 N5 118.6(5) . . ? C22 C23 C24 118.8(5) . . ? C22 C23 H23A 120.6 . . ? C24 C23 H23A 120.6 . . ? C25 C24 C23 120.1(6) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C26 C25 C24 119.9(6) . . ? C26 C25 H25A 120.0 . . ? C24 C25 H25A 120.0 . . ? C25 C26 C27 120.7(6) . . ? C25 C26 H26A 119.6 . . ? C27 C26 H26A 119.6 . . ? C22 C27 C26 118.5(6) . . ? C22 C27 H27A 120.8 . . ? C26 C27 H27A 120.8 . . ? N5 C28 C29 131.7(5) . . ? N5 C28 C33 105.8(4) . . ? C29 C28 C33 122.5(5) . . ? C30 C29 C28 116.4(5) . . ? C30 C29 H29A 121.8 . . ? C28 C29 H29A 121.8 . . ? C29 C30 C31 122.2(5) . . ? C29 C30 H30A 118.9 . . ? C31 C30 H30A 118.9 . . ? C32 C31 C30 121.4(5) . . ? C32 C31 H31A 119.3 . . ? C30 C31 H31A 119.3 . . ? C31 C32 C33 117.5(5) . . ? C31 C32 H32A 121.2 . . ? C33 C32 H32A 121.2 . . ? N4 C33 C28 109.4(4) . . ? N4 C33 C32 130.6(5) . . ? C28 C33 C32 119.9(5) . . ? C35 C34 C39 117.6(5) . . ? C35 C34 H34A 121.2 . . ? C39 C34 H34A 121.2 . . ? C34 C35 C36 121.3(5) . . ? C34 C35 H35A 119.4 . . ? C36 C35 H35A 119.4 . . ? C37 C36 C35 122.1(5) . . ? C37 C36 H36A 119.0 . . ? C35 C36 H36A 119.0 . . ? C36 C37 C38 116.8(5) . . ? C36 C37 H37A 121.6 . . ? C38 C37 H37A 121.6 . . ? N10 C38 C39 106.2(4) . . ? N10 C38 C37 131.3(5) . . ? C39 C38 C37 122.4(5) . . ? N9 C39 C38 109.3(5) . . ? N9 C39 C34 130.7(5) . . ? C38 C39 C34 120.0(5) . . ? C46 C41 C42 121.6(5) . . ? C46 C41 N10 120.1(5) . . ? C42 C41 N10 118.3(5) . . ? C43 C42 C41 117.6(6) . . ? C43 C42 H42A 121.2 . . ? C41 C42 H42A 121.2 . . ? C44 C43 C42 121.7(7) . . ? C44 C43 H43A 119.2 . . ? C42 C43 H43A 119.2 . . ? C43 C44 C45 119.8(6) . . ? C43 C44 H44A 120.1 . . ? C45 C44 H44A 120.1 . . ? C46 C45 C44 120.3(7) . . ? C46 C45 H45A 119.8 . . ? C44 C45 H45A 119.8 . . ? C41 C46 C45 119.0(6) . . ? C41 C46 H46A 120.5 . . ? C45 C46 H46A 120.5 . . ? N9 C47 N10 112.7(5) . . ? N9 C47 C48 119.5(5) . . ? N10 C47 C48 127.8(5) . . ? N8 C48 C49 120.9(5) . . ? N8 C48 C47 110.7(4) . . ? C49 C48 C47 128.3(5) . . ? C48 C49 C50 117.8(5) . . ? C48 C49 H49A 121.1 . . ? C50 C49 H49A 121.1 . . ? C51 C50 C49 120.9(5) . . ? C51 C50 H50A 119.5 . . ? C49 C50 H50A 119.5 . . ? C50 C51 C52 117.7(5) . . ? C50 C51 H51A 121.2 . . ? C52 C51 H51A 121.2 . . ? N8 C52 C51 121.6(5) . . ? N8 C52 C53 110.6(4) . . ? C51 C52 C53 127.8(5) . . ? N6 C53 N7 112.3(5) . . ? N6 C53 C52 119.3(4) . . ? N7 C53 C52 128.3(5) . . ? C60 C55 C56 121.5(5) . . ? C60 C55 N7 119.3(5) . . ? C56 C55 N7 119.2(5) . . ? C57 C56 C55 119.1(5) . . ? C57 C56 H56A 120.4 . . ? C55 C56 H56A 120.4 . . ? C58 C57 C56 120.1(6) . . ? C58 C57 H57A 120.0 . . ? C56 C57 H57A 120.0 . . ? C59 C58 C57 120.2(6) . . ? C59 C58 H58A 119.9 . . ? C57 C58 H58A 119.9 . . ? C58 C59 C60 120.9(6) . . ? C58 C59 H59A 119.6 . . ? C60 C59 H59A 119.6 . . ? C55 C60 C59 118.2(5) . . ? C55 C60 H60A 120.9 . . ? C59 C60 H60A 120.9 . . ? C62 C61 N7 131.7(5) . . ? C62 C61 C66 122.7(5) . . ? N7 C61 C66 105.5(5) . . ? C61 C62 C63 115.9(5) . . ? C61 C62 H62A 122.0 . . ? C63 C62 H62A 122.0 . . ? C62 C63 C64 121.6(5) . . ? C62 C63 H63A 119.2 . . ? C64 C63 H63A 119.2 . . ? C65 C64 C63 122.5(6) . . ? C65 C64 H64A 118.7 . . ? C63 C64 H64A 118.7 . . ? C64 C65 C66 116.9(5) . . ? C64 C65 H65A 121.6 . . ? C66 C65 H65A 121.6 . . ? N6 C66 C61 109.3(5) . . ? N6 C66 C65 130.3(5) . . ? C61 C66 C65 120.4(5) . . ? O4 Cl1 O1 113.9(5) . . ? O4 Cl1 O2 109.8(4) . . ? O1 Cl1 O2 111.0(3) . . ? O4 Cl1 O3 108.1(5) . . ? O1 Cl1 O3 106.5(4) . . ? O2 Cl1 O3 107.3(4) . . ? O5 Cl2 O7 126.7(5) . . ? O5 Cl2 O6 119.0(5) . . ? O7 Cl2 O6 113.9(5) . . ? O5 Cl2 O8 85.9(7) . . ? O7 Cl2 O8 94.5(8) . . ? O6 Cl2 O8 96.5(8) . . ? C67 O9 H9 112.9 . . ? O9 C67 C682 102.6(16) . . ? O9 C67 C681 108.7(13) . . ? C682 C67 C681 122(2) . . ? O9 C67 H67A 109.9 . . ? C682 C67 H67A 12.5 . . ? C681 C67 H67A 109.9 . . ? O9 C67 H67B 109.9 . . ? C682 C67 H67B 102.6 . . ? C681 C67 H67B 109.9 . . ? H67A C67 H67B 108.3 . . ? C67 C681 H68A 109.5 . . ? C67 C681 H68B 109.5 . . ? C67 C681 H68C 109.5 . . ? C67 C682 H68D 109.5 . . ? C67 C682 H68E 109.5 . . ? H68D C682 H68E 109.5 . . ? C67 C682 H68F 109.5 . . ? H68D C682 H68F 109.5 . . ? H68E C682 H68F 109.5 . . ? H201 O2W H202 109.0 . . ? H201 O1W H101 97.3 . . ? H201 O1W H102 105.8 . . ? H101 O1W H102 107.1 . . ? 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 N3 Zn1 N1 C14 -7.3(3) . . . . ? N6 Zn1 N1 C14 105.3(4) . . . . ? N8 Zn1 N1 C14 179.4(3) . . . . ? N4 Zn1 N1 C14 -11.4(6) . . . . ? N9 Zn1 N1 C14 -105.2(4) . . . . ? N3 Zn1 N1 C6 -169.2(5) . . . . ? N6 Zn1 N1 C6 -56.5(5) . . . . ? N8 Zn1 N1 C6 17.6(6) . . . . ? N4 Zn1 N1 C6 -173.3(4) . . . . ? N9 Zn1 N1 C6 92.9(5) . . . . ? N6 Zn1 N3 C15 -83.3(4) . . . . ? N8 Zn1 N3 C15 133.1(10) . . . . ? N1 Zn1 N3 C15 0.6(4) . . . . ? N4 Zn1 N3 C15 178.6(4) . . . . ? N9 Zn1 N3 C15 92.9(4) . . . . ? N6 Zn1 N3 C19 107.9(4) . . . . ? N8 Zn1 N3 C19 -35.7(12) . . . . ? N1 Zn1 N3 C19 -168.2(4) . . . . ? N4 Zn1 N3 C19 9.8(4) . . . . ? N9 Zn1 N3 C19 -75.8(4) . . . . ? N3 Zn1 N4 C20 -10.3(3) . . . . ? N6 Zn1 N4 C20 -120.0(3) . . . . ? N8 Zn1 N4 C20 163.5(3) . . . . ? N1 Zn1 N4 C20 -6.2(6) . . . . ? N9 Zn1 N4 C20 89.2(4) . . . . ? N3 Zn1 N4 C33 -166.2(5) . . . . ? N6 Zn1 N4 C33 84.2(5) . . . . ? N8 Zn1 N4 C33 7.6(5) . . . . ? N1 Zn1 N4 C33 -162.1(4) . . . . ? N9 Zn1 N4 C33 -66.6(5) . . . . ? N3 Zn1 N6 C53 -170.6(3) . . . . ? N8 Zn1 N6 C53 4.1(3) . . . . ? N1 Zn1 N6 C53 114.7(4) . . . . ? N4 Zn1 N6 C53 -91.2(4) . . . . ? N9 Zn1 N6 C53 16.6(5) . . . . ? N3 Zn1 N6 C66 21.4(6) . . . . ? N8 Zn1 N6 C66 -163.9(5) . . . . ? N1 Zn1 N6 C66 -53.3(5) . . . . ? N4 Zn1 N6 C66 100.7(5) . . . . ? N9 Zn1 N6 C66 -151.4(5) . . . . ? N3 Zn1 N8 C52 131.1(10) . . . . ? N6 Zn1 N8 C52 -14.2(4) . . . . ? N1 Zn1 N8 C52 -98.3(4) . . . . ? N4 Zn1 N8 C52 86.9(4) . . . . ? N9 Zn1 N8 C52 172.5(4) . . . . ? N3 Zn1 N8 C48 -30.0(12) . . . . ? N6 Zn1 N8 C48 -175.3(4) . . . . ? N1 Zn1 N8 C48 100.5(4) . . . . ? N4 Zn1 N8 C48 -74.2(4) . . . . ? N9 Zn1 N8 C48 11.4(4) . . . . ? N3 Zn1 N9 C47 173.7(4) . . . . ? N6 Zn1 N9 C47 -13.1(5) . . . . ? N8 Zn1 N9 C47 -0.5(3) . . . . ? N1 Zn1 N9 C47 -109.9(4) . . . . ? N4 Zn1 N9 C47 98.6(4) . . . . ? N3 Zn1 N9 C39 -22.2(5) . . . . ? N6 Zn1 N9 C39 151.0(5) . . . . ? N8 Zn1 N9 C39 163.5(5) . . . . ? N1 Zn1 N9 C39 54.2(5) . . . . ? N4 Zn1 N9 C39 -97.3(5) . . . . ? C6 C1 C2 C3 0.2(8) . . . . ? C1 C2 C3 C4 0.1(9) . . . . ? C2 C3 C4 C5 -0.3(8) . . . . ? C14 N2 C5 C6 0.6(5) . . . . ? C8 N2 C5 C6 -166.8(5) . . . . ? C14 N2 C5 C4 -179.8(6) . . . . ? C8 N2 C5 C4 12.8(9) . . . . ? C3 C4 C5 C6 0.2(8) . . . . ? C3 C4 C5 N2 -179.3(5) . . . . ? C14 N1 C6 C5 1.6(6) . . . . ? Zn1 N1 C6 C5 164.2(4) . . . . ? C14 N1 C6 C1 -179.6(5) . . . . ? Zn1 N1 C6 C1 -17.0(9) . . . . ? N2 C5 C6 N1 -1.4(6) . . . . ? C4 C5 C6 N1 179.0(5) . . . . ? N2 C5 C6 C1 179.7(5) . . . . ? C4 C5 C6 C1 0.1(8) . . . . ? C2 C1 C6 N1 -178.9(5) . . . . ? C2 C1 C6 C5 -0.2(8) . . . . ? C14 N2 C8 C13 -58.8(7) . . . . ? C5 N2 C8 C13 105.9(6) . . . . ? C14 N2 C8 C9 122.1(6) . . . . ? C5 N2 C8 C9 -73.3(7) . . . . ? C13 C8 C9 C10 -0.6(9) . . . . ? N2 C8 C9 C10 178.5(5) . . . . ? C8 C9 C10 C11 0.3(10) . . . . ? C9 C10 C11 C12 0.4(11) . . . . ? C10 C11 C12 C13 -0.7(10) . . . . ? C9 C8 C13 C12 0.3(9) . . . . ? N2 C8 C13 C12 -178.8(5) . . . . ? C11 C12 C13 C8 0.4(9) . . . . ? C6 N1 C14 N2 -1.2(6) . . . . ? Zn1 N1 C14 N2 -168.8(3) . . . . ? C6 N1 C14 C15 -179.2(4) . . . . ? Zn1 N1 C14 C15 13.2(6) . . . . ? C5 N2 C14 N1 0.4(6) . . . . ? C8 N2 C14 N1 167.3(5) . . . . ? C5 N2 C14 C15 178.2(5) . . . . ? C8 N2 C14 C15 -14.9(8) . . . . ? C19 N3 C15 C16 0.0(7) . . . . ? Zn1 N3 C15 C16 -168.5(4) . . . . ? C19 N3 C15 C14 174.0(4) . . . . ? Zn1 N3 C15 C14 5.5(5) . . . . ? N1 C14 C15 N3 -12.6(7) . . . . ? N2 C14 C15 N3 169.8(5) . . . . ? N1 C14 C15 C16 160.9(5) . . . . ? N2 C14 C15 C16 -16.7(9) . . . . ? N3 C15 C16 C17 -0.5(8) . . . . ? C14 C15 C16 C17 -173.5(5) . . . . ? C15 C16 C17 C18 1.2(8) . . . . ? C16 C17 C18 C19 -1.4(9) . . . . ? C15 N3 C19 C18 -0.2(7) . . . . ? Zn1 N3 C19 C18 168.3(4) . . . . ? C15 N3 C19 C20 -175.8(4) . . . . ? Zn1 N3 C19 C20 -7.4(5) . . . . ? C17 C18 C19 N3 0.9(8) . . . . ? C17 C18 C19 C20 175.6(5) . . . . ? C33 N4 C20 N5 0.2(6) . . . . ? Zn1 N4 C20 N5 -163.4(3) . . . . ? C33 N4 C20 C19 174.0(4) . . . . ? Zn1 N4 C20 C19 10.4(6) . . . . ? C28 N5 C20 N4 1.4(6) . . . . ? C22 N5 C20 N4 -175.1(5) . . . . ? C28 N5 C20 C19 -171.9(5) . . . . ? C22 N5 C20 C19 11.6(8) . . . . ? N3 C19 C20 N4 -2.5(7) . . . . ? C18 C19 C20 N4 -177.6(5) . . . . ? N3 C19 C20 N5 170.3(5) . . . . ? C18 C19 C20 N5 -4.8(9) . . . . ? C20 N5 C22 C27 -107.9(6) . . . . ? C28 N5 C22 C27 76.1(7) . . . . ? C20 N5 C22 C23 71.6(7) . . . . ? C28 N5 C22 C23 -104.4(6) . . . . ? C27 C22 C23 C24 1.8(8) . . . . ? N5 C22 C23 C24 -177.7(5) . . . . ? C22 C23 C24 C25 -1.0(8) . . . . ? C23 C24 C25 C26 -0.3(9) . . . . ? C24 C25 C26 C27 0.9(10) . . . . ? C23 C22 C27 C26 -1.2(9) . . . . ? N5 C22 C27 C26 178.3(5) . . . . ? C25 C26 C27 C22 -0.2(10) . . . . ? C20 N5 C28 C29 177.0(6) . . . . ? C22 N5 C28 C29 -6.2(9) . . . . ? C20 N5 C28 C33 -2.4(5) . . . . ? C22 N5 C28 C33 174.3(5) . . . . ? N5 C28 C29 C30 -179.6(5) . . . . ? C33 C28 C29 C30 -0.3(8) . . . . ? C28 C29 C30 C31 -0.9(8) . . . . ? C29 C30 C31 C32 0.5(9) . . . . ? C30 C31 C32 C33 1.0(8) . . . . ? C20 N4 C33 C28 -1.7(5) . . . . ? Zn1 N4 C33 C28 155.2(4) . . . . ? C20 N4 C33 C32 179.7(5) . . . . ? Zn1 N4 C33 C32 -23.3(8) . . . . ? N5 C28 C33 N4 2.6(5) . . . . ? C29 C28 C33 N4 -176.9(5) . . . . ? N5 C28 C33 C32 -178.7(4) . . . . ? C29 C28 C33 C32 1.8(8) . . . . ? C31 C32 C33 N4 176.3(5) . . . . ? C31 C32 C33 C28 -2.1(7) . . . . ? C39 C34 C35 C36 -1.1(8) . . . . ? C34 C35 C36 C37 -0.2(9) . . . . ? C35 C36 C37 C38 0.1(9) . . . . ? C47 N10 C38 C39 0.6(5) . . . . ? C41 N10 C38 C39 176.5(5) . . . . ? C47 N10 C38 C37 -175.3(6) . . . . ? C41 N10 C38 C37 0.6(9) . . . . ? C36 C37 C38 N10 176.6(5) . . . . ? C36 C37 C38 C39 1.3(8) . . . . ? C47 N9 C39 C38 1.0(6) . . . . ? Zn1 N9 C39 C38 -163.9(4) . . . . ? C47 N9 C39 C34 178.6(5) . . . . ? Zn1 N9 C39 C34 13.8(9) . . . . ? N10 C38 C39 N9 -1.0(6) . . . . ? C37 C38 C39 N9 175.4(5) . . . . ? N10 C38 C39 C34 -179.0(4) . . . . ? C37 C38 C39 C34 -2.6(8) . . . . ? C35 C34 C39 N9 -175.1(5) . . . . ? C35 C34 C39 C38 2.4(7) . . . . ? C47 N10 C41 C46 56.2(8) . . . . ? C38 N10 C41 C46 -118.7(6) . . . . ? C47 N10 C41 C42 -124.1(6) . . . . ? C38 N10 C41 C42 60.9(7) . . . . ? C46 C41 C42 C43 0.6(9) . . . . ? N10 C41 C42 C43 -179.1(5) . . . . ? C41 C42 C43 C44 -0.8(10) . . . . ? C42 C43 C44 C45 0.5(11) . . . . ? C43 C44 C45 C46 0.1(11) . . . . ? C42 C41 C46 C45 0.0(9) . . . . ? N10 C41 C46 C45 179.6(6) . . . . ? C44 C45 C46 C41 -0.3(10) . . . . ? C39 N9 C47 N10 -0.6(6) . . . . ? Zn1 N9 C47 N10 168.6(3) . . . . ? C39 N9 C47 C48 -178.5(4) . . . . ? Zn1 N9 C47 C48 -9.4(6) . . . . ? C38 N10 C47 N9 0.0(6) . . . . ? C41 N10 C47 N9 -175.8(5) . . . . ? C38 N10 C47 C48 177.7(5) . . . . ? C41 N10 C47 C48 2.0(9) . . . . ? C52 N8 C48 C49 -1.8(8) . . . . ? Zn1 N8 C48 C49 158.6(5) . . . . ? C52 N8 C48 C47 -179.1(5) . . . . ? Zn1 N8 C48 C47 -18.7(6) . . . . ? N9 C47 C48 N8 18.4(7) . . . . ? N10 C47 C48 N8 -159.2(5) . . . . ? N9 C47 C48 C49 -158.6(6) . . . . ? N10 C47 C48 C49 23.8(9) . . . . ? N8 C48 C49 C50 0.1(9) . . . . ? C47 C48 C49 C50 176.9(6) . . . . ? C48 C49 C50 C51 1.4(10) . . . . ? C49 C50 C51 C52 -1.2(10) . . . . ? C48 N8 C52 C51 2.0(8) . . . . ? Zn1 N8 C52 C51 -158.6(4) . . . . ? C48 N8 C52 C53 -179.3(4) . . . . ? Zn1 N8 C52 C53 20.1(5) . . . . ? C50 C51 C52 N8 -0.5(9) . . . . ? C50 C51 C52 C53 -178.9(6) . . . . ? C66 N6 C53 N7 -0.9(6) . . . . ? Zn1 N6 C53 N7 -172.6(3) . . . . ? C66 N6 C53 C52 176.9(4) . . . . ? Zn1 N6 C53 C52 5.2(6) . . . . ? C61 N7 C53 N6 0.6(6) . . . . ? C55 N7 C53 N6 174.0(5) . . . . ? C61 N7 C53 C52 -176.9(5) . . . . ? C55 N7 C53 C52 -3.5(8) . . . . ? N8 C52 C53 N6 -16.7(7) . . . . ? C51 C52 C53 N6 161.9(5) . . . . ? N8 C52 C53 N7 160.7(5) . . . . ? C51 C52 C53 N7 -20.7(9) . . . . ? C53 N7 C55 C60 124.1(6) . . . . ? C61 N7 C55 C60 -63.7(7) . . . . ? C53 N7 C55 C56 -54.8(7) . . . . ? C61 N7 C55 C56 117.4(6) . . . . ? C60 C55 C56 C57 -2.3(9) . . . . ? N7 C55 C56 C57 176.6(5) . . . . ? C55 C56 C57 C58 1.8(9) . . . . ? C56 C57 C58 C59 -0.2(10) . . . . ? C57 C58 C59 C60 -1.0(10) . . . . ? C56 C55 C60 C59 1.1(9) . . . . ? N7 C55 C60 C59 -177.7(5) . . . . ? C58 C59 C60 C55 0.5(9) . . . . ? C53 N7 C61 C62 179.1(6) . . . . ? C55 N7 C61 C62 5.5(9) . . . . ? C53 N7 C61 C66 -0.2(5) . . . . ? C55 N7 C61 C66 -173.7(5) . . . . ? N7 C61 C62 C63 -177.5(6) . . . . ? C66 C61 C62 C63 1.6(8) . . . . ? C61 C62 C63 C64 -1.8(9) . . . . ? C62 C63 C64 C65 0.5(10) . . . . ? C63 C64 C65 C66 1.1(9) . . . . ? C53 N6 C66 C61 0.7(6) . . . . ? Zn1 N6 C66 C61 169.3(4) . . . . ? C53 N6 C66 C65 -178.8(5) . . . . ? Zn1 N6 C66 C65 -10.2(9) . . . . ? C62 C61 C66 N6 -179.7(5) . . . . ? N7 C61 C66 N6 -0.4(6) . . . . ? C62 C61 C66 C65 -0.1(8) . . . . ? N7 C61 C66 C65 179.2(5) . . . . ? C64 C65 C66 N6 178.2(5) . . . . ? C64 C65 C66 C61 -1.3(8) . . . . ? 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 O9 H9 O8 0.85 2.14 2.99(2) 179.0 2_667 O2W H202 O6 0.85 2.14 2.941(12) 158.9 2_677 O1W H101 O5 0.84 2.61 3.15(2) 123.9 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.928 _refine_diff_density_min -1.974 _refine_diff_density_rms 0.116 ##### end of cif #####