# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email wubiao@lzb.ac.cn _publ_contact_author_name 'Wu, Biao' loop_ _publ_author_name 'Yana Xia' 'Li Shaoguang' 'Biao Wu' 'Yanyan Liu' 'Xiao-Juan Yang' ############ data_X3 _database_code_depnum_ccdc_archive 'CCDC 767961' #TrackingRef '- complexes.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H64 Cu N10 O26' _chemical_formula_weight 1116.51 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Ccca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1, -y+1/2, z' '-x+1/2, y+1/2, -z+1/2' 'x+1, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' '-x+1/2, -y+1/2, -z' 'x, y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' '-x, y+1/2, z-1/2' _cell_length_a 10.4135(5) _cell_length_b 25.2037(13) _cell_length_c 19.5818(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5139.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2348 _exptl_absorpt_coefficient_mu 0.520 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8350 _exptl_absorpt_correction_T_max 0.8987 _exptl_absorpt_process_details SADABS _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 'Bruker APEX II area detector' _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 12134 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 24.66 _reflns_number_total 2180 _reflns_number_gt 1781 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _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 ? _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. Two DFIX restraints [O-H = 0.85(2)angstrom] were used to refine two H atoms (H7C and H7D) located on water molecule O7. ; _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^)+(0.0430P)^2^+8.4022P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2180 _refine_ls_number_parameters 179 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.078 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.0000 0.2500 0.2500 0.03110(19) Uani 1 4 d S . . C1 C 0.2393(2) 0.28141(10) 0.17894(13) 0.0379(6) Uani 1 1 d . . . H1A H 0.2432 0.3071 0.2130 0.045 Uiso 1 1 calc R . . C2 C 0.3373(2) 0.27798(11) 0.13207(14) 0.0432(7) Uani 1 1 d . . . H2A H 0.4064 0.3013 0.1346 0.052 Uiso 1 1 calc R . . C3 C 0.3335(2) 0.24013(10) 0.08140(14) 0.0411(6) Uani 1 1 d . . . H3A H 0.3992 0.2378 0.0493 0.049 Uiso 1 1 calc R . . C4 C 0.2300(2) 0.20548(9) 0.07900(12) 0.0320(5) Uani 1 1 d . . . C5 C 0.1336(2) 0.21159(9) 0.12723(12) 0.0312(5) Uani 1 1 d . . . H5A H 0.0629 0.1891 0.1253 0.037 Uiso 1 1 calc R . . C6 C 0.3089(2) 0.14625(10) -0.01181(13) 0.0376(6) Uani 1 1 d . . . C7 C 0.3530(3) 0.08446(11) -0.09830(15) 0.0506(7) Uani 1 1 d . . . H7A H 0.4229 0.0681 -0.0733 0.061 Uiso 1 1 calc R . . H7B H 0.3886 0.1119 -0.1274 0.061 Uiso 1 1 calc R . . C8 C 0.2858(3) 0.04391(11) -0.14056(14) 0.0513(7) Uani 1 1 d . . . H8A H 0.2098 0.0595 -0.1611 0.062 Uiso 1 1 calc R . . H8B H 0.3420 0.0321 -0.1770 0.062 Uiso 1 1 calc R . . C9 C 0.5832(6) 0.4655(3) 0.0796(2) 0.142(2) Uani 1 1 d . . . H9A H 0.6220 0.4874 0.0451 0.213 Uiso 1 1 calc R . . H9B H 0.4951 0.4590 0.0679 0.213 Uiso 1 1 calc R . . H9C H 0.6285 0.4324 0.0825 0.213 Uiso 1 1 calc R . . N1 N 0.13782(18) 0.24835(8) 0.17644(10) 0.0313(4) Uani 1 1 d . . . N2 N 0.21583(19) 0.16505(8) 0.03024(11) 0.0375(5) Uani 1 1 d . . . H2B H 0.1410 0.1508 0.0267 0.045 Uiso 1 1 calc R . . N3 N 0.5000 0.3845(2) 0.2500 0.0989(18) Uani 1 2 d S . . O1 O 0.41856(17) 0.16193(8) -0.01423(10) 0.0518(5) Uani 1 1 d . . . O2 O 0.26131(17) 0.10750(7) -0.05096(9) 0.0449(5) Uani 1 1 d . . . O3 O 0.2500 0.0000 -0.09949(13) 0.0480(7) Uani 1 2 d S . . O4 O 0.0000 0.34668(10) 0.2500 0.0484(7) Uani 1 2 d S . . H4A H 0.0622 0.3575 0.2715 0.073 Uiso 0.50 1 calc PR . . O5 O 0.5000 0.4346(2) 0.2500 0.138(2) Uani 1 2 d S . . O6 O 0.5776(4) 0.36181(18) 0.2154(3) 0.1526(17) Uani 1 1 d . . . O7 O 0.8310(4) 0.40779(14) 0.1804(2) 0.0964(10) Uani 1 1 d D . . H7C H 0.844(4) 0.4413(8) 0.178(2) 0.091(15) Uiso 1 1 d D . . H7D H 0.759(4) 0.401(2) 0.199(3) 0.16(3) Uiso 1 1 d D . . O8 O 0.5893(4) 0.49194(15) 0.14369(19) 0.1266(12) Uani 1 1 d . . . H8C H 0.5828 0.4701 0.1746 0.190 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 Cu 0.0241(3) 0.0410(4) 0.0282(3) 0.000 0.000 0.000 C1 0.0331(13) 0.0388(14) 0.0416(14) -0.0024(11) -0.0004(11) -0.0037(11) C2 0.0296(13) 0.0462(16) 0.0538(17) -0.0025(13) 0.0040(12) -0.0120(11) C3 0.0280(13) 0.0486(17) 0.0465(15) -0.0015(12) 0.0098(11) -0.0051(11) C4 0.0264(12) 0.0348(13) 0.0349(13) 0.0029(10) 0.0009(10) -0.0001(10) C5 0.0240(11) 0.0360(13) 0.0337(13) 0.0034(11) 0.0009(10) -0.0037(10) C6 0.0377(14) 0.0355(13) 0.0395(14) 0.0017(11) 0.0061(11) 0.0014(11) C7 0.0550(17) 0.0423(16) 0.0546(18) -0.0059(13) 0.0199(14) 0.0003(13) C8 0.070(2) 0.0416(15) 0.0419(16) 0.0000(13) 0.0101(14) 0.0022(14) C9 0.153(5) 0.180(6) 0.093(4) -0.049(4) -0.032(4) 0.082(4) N1 0.0259(9) 0.0359(11) 0.0320(10) -0.0001(9) 0.0003(8) -0.0013(9) N2 0.0275(10) 0.0429(12) 0.0422(12) -0.0058(10) 0.0079(9) -0.0062(9) N3 0.093(4) 0.072(4) 0.131(5) 0.000 -0.046(4) 0.000 O1 0.0330(10) 0.0575(12) 0.0650(13) -0.0140(10) 0.0149(9) -0.0046(9) O2 0.0428(10) 0.0420(10) 0.0500(11) -0.0106(9) 0.0137(9) -0.0031(8) O3 0.0665(18) 0.0409(14) 0.0366(14) 0.000 0.000 -0.0054(13) O4 0.0484(16) 0.0440(15) 0.0528(17) 0.000 -0.0128(13) 0.000 O5 0.223(7) 0.089(4) 0.103(4) 0.000 -0.028(4) 0.000 O6 0.113(3) 0.111(3) 0.233(5) -0.007(3) -0.002(3) 0.019(2) O7 0.092(2) 0.069(2) 0.129(3) -0.0028(19) -0.037(2) 0.0262(18) O8 0.134(3) 0.118(3) 0.128(3) -0.031(2) -0.001(3) 0.018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 2.0337(19) 6_455 ? Cu N1 2.0337(19) 8_455 ? Cu N1 2.0337(19) . ? Cu N1 2.0337(19) 3 ? Cu O4 2.437(3) 6_455 ? Cu O4 2.437(3) . ? C1 N1 1.347(3) . ? C1 C2 1.375(4) . ? C2 C3 1.377(4) . ? C3 C4 1.388(3) . ? C4 C5 1.387(3) . ? C4 N2 1.404(3) . ? C5 N1 1.337(3) . ? C6 O1 1.209(3) 1 ? C6 O1 1.209(3) . ? C6 O2 1.337(3) . ? C6 N2 1.357(3) . ? C7 O2 1.452(3) . ? C7 C8 1.490(4) . ? C8 O3 1.418(3) . ? C9 O8 1.422(5) . ? N3 O6 1.200(4) 1 ? N3 O6 1.200(4) . ? N3 O6 1.200(4) 3_655 ? N3 O5 1.262(7) . ? N3 O5 1.262(7) 1 ? O1 O1 0.000(7) 1 ? O3 C8 1.418(3) 2 ? O5 O5 0.000(11) 1 ? O6 O6 0.000(14) 1 ? 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 Cu N1 177.65(12) 6_455 8_455 ? N1 Cu N1 89.82(10) 6_455 . ? N1 Cu N1 90.23(11) 8_455 . ? N1 Cu N1 90.23(10) 6_455 3 ? N1 Cu N1 89.82(10) 8_455 3 ? N1 Cu N1 177.65(12) . 3 ? N1 Cu O4 91.17(6) 6_455 6_455 ? N1 Cu O4 91.17(6) 8_455 6_455 ? N1 Cu O4 88.83(6) . 6_455 ? N1 Cu O4 88.83(6) 3 6_455 ? N1 Cu O4 88.83(6) 6_455 . ? N1 Cu O4 88.83(6) 8_455 . ? N1 Cu O4 91.17(6) . . ? N1 Cu O4 91.17(6) 3 . ? O4 Cu O4 180.0 6_455 . ? N1 C1 C2 121.3(2) . . ? C1 C2 C3 120.2(2) . . ? C2 C3 C4 118.8(2) . . ? C5 C4 C3 118.0(2) . . ? C5 C4 N2 117.9(2) . . ? C3 C4 N2 124.1(2) . . ? N1 C5 C4 122.9(2) . . ? O1 C6 O1 0.0(3) 1 . ? O1 C6 O2 124.5(2) 1 . ? O1 C6 O2 124.5(2) . . ? O1 C6 N2 125.7(2) 1 . ? O1 C6 N2 125.7(2) . . ? O2 C6 N2 109.7(2) . . ? O2 C7 C8 108.6(2) . . ? O3 C8 C7 110.1(2) . . ? C5 N1 C1 118.7(2) . . ? C5 N1 Cu 120.08(15) . . ? C1 N1 Cu 121.03(17) . . ? C6 N2 C4 126.2(2) . . ? O6 N3 O6 0.0(6) 1 . ? O6 N3 O6 123.0(7) 1 3_655 ? O6 N3 O6 123.0(7) . 3_655 ? O6 N3 O5 118.5(3) 1 . ? O6 N3 O5 118.5(3) . . ? O6 N3 O5 118.5(3) 3_655 . ? O6 N3 O5 118.5(3) 1 1 ? O6 N3 O5 118.5(3) . 1 ? O6 N3 O5 118.5(3) 3_655 1 ? O5 N3 O5 0.000(1) . 1 ? O1 O1 C6 0(10) 1 . ? C6 O2 C7 114.5(2) . . ? C8 O3 C8 110.9(3) 2 . ? O5 O5 N3 0(10) 1 . ? O6 O6 N3 0(10) 1 . ? 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 O4 H4A O7 0.82 1.93 2.707(3) 157.6 3_655 O7 H7C O8 0.856(19) 1.94(2) 2.755(6) 158(4) 2_665 O7 H7D O6 0.86(2) 2.15(3) 2.963(6) 158(6) 1 O8 H8C O5 0.82 1.93 2.700(5) 155.9 1 N2 H2B O1 0.86 2.35 3.112(3) 148.5 10 C3 H3A O1 0.93 2.29 2.859(3) 118.9 1 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.66 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.362 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.048 data_x1 _database_code_depnum_ccdc_archive 'CCDC 819732' #TrackingRef '- complexes.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H42 Cl4 N8 O13 Zn2' _chemical_formula_weight 1019.28 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' 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 Monoclinic _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 15.84(2) _cell_length_b 24.75(2) _cell_length_c 7.724(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.88(2) _cell_angle_gamma 90.00 _cell_volume 3026(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.119 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 1.018 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6744 _exptl_absorpt_correction_T_max 0.7431 _exptl_absorpt_process_details SADABS _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 'Bruker APEX II area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7351 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2732 _reflns_number_gt 2197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 -0.036 393 62 ' ' 2 0.500 0.000 -0.003 393 62 ' ' _platon_squeeze_details ; ; _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^)+(0.1135P)^2^+2.6455P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2732 _refine_ls_number_parameters 149 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1282 _refine_ls_goodness_of_fit_ref 0.809 _refine_ls_restrained_S_all 0.811 _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 Zn Zn 0.0000 0.186818(18) 0.5000 0.0439(2) Uani 1 2 d S . . Cl Cl 0.07257(5) 0.14332(4) 0.71649(11) 0.0697(3) Uani 1 1 d . . . N1 N 0.08033(14) 0.23909(9) 0.3740(3) 0.0456(6) Uani 1 1 d . . . N2 N 0.2387(2) 0.34682(12) 0.4837(3) 0.0680(8) Uani 1 1 d . . . H2A H 0.2703 0.3667 0.4227 0.082 Uiso 1 1 calc R . . O1 O 0.2070(2) 0.33029(12) 0.7648(3) 0.0928(10) Uani 1 1 d . . . O2 O 0.30466(17) 0.39306(10) 0.6973(3) 0.0703(7) Uani 1 1 d . . . O3 O 0.3333(2) 0.5000 0.8567(4) 0.0649(9) Uani 1 2 d S . . C1 C 0.13007(18) 0.27372(12) 0.4678(4) 0.0478(7) Uani 1 1 d . . . H1A H 0.1274 0.2737 0.5878 0.057 Uiso 1 1 calc R . . C2 C 0.1857(2) 0.30975(13) 0.3909(4) 0.0540(8) Uani 1 1 d . . . C3 C 0.1887(3) 0.30846(17) 0.2087(5) 0.0787(12) Uani 1 1 d . . . H3A H 0.2244 0.3317 0.1524 0.094 Uiso 1 1 calc R . . C4 C 0.1383(3) 0.27226(19) 0.1145(5) 0.0902(14) Uani 1 1 d . . . H4A H 0.1405 0.2706 -0.0055 0.108 Uiso 1 1 calc R . . C5 C 0.0841(2) 0.23824(15) 0.2002(4) 0.0642(9) Uani 1 1 d . . . H5A H 0.0497 0.2144 0.1359 0.077 Uiso 1 1 calc R . . C6 C 0.2454(2) 0.35466(13) 0.6594(4) 0.0572(8) Uani 1 1 d . . . C7 C 0.3220(3) 0.40362(15) 0.8807(5) 0.0792(11) Uani 1 1 d . . . H7A H 0.3485 0.3723 0.9359 0.095 Uiso 1 1 calc R . . H7B H 0.2697 0.4109 0.9363 0.095 Uiso 1 1 calc R . . C8 C 0.3800(2) 0.45175(13) 0.8990(5) 0.0693(10) Uani 1 1 d . . . H8A H 0.4038 0.4539 1.0170 0.083 Uiso 1 1 calc R . . H8B H 0.4261 0.4479 0.8219 0.083 Uiso 1 1 calc R . . O4 O 0.2461(16) 0.4731(7) 0.303(2) 0.384(16) Uani 0.50 1 d PD . . H402 H 0.229(4) 0.5000 0.372(6) 0.10(3) Uiso 1 2 d SD . . H401 H 0.2797(16) 0.4494(11) 0.292(4) -0.016(6) Uiso 0.50 1 d PD . . O5 O 0.5000 0.5000 0.5000 0.69(5) Uani 1 4 d S . . 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 Zn 0.0428(3) 0.0493(3) 0.0398(3) 0.000 0.00314(19) 0.000 Cl 0.0585(5) 0.0877(6) 0.0631(5) 0.0317(5) 0.0049(4) 0.0111(4) N1 0.0460(13) 0.0530(13) 0.0379(12) 0.0049(11) 0.0028(10) 0.0009(11) N2 0.084(2) 0.0761(19) 0.0446(15) 0.0089(14) 0.0094(14) -0.0377(16) O1 0.137(3) 0.0943(18) 0.0488(14) 0.0019(14) 0.0164(15) -0.0604(19) O2 0.0946(18) 0.0653(14) 0.0508(13) 0.0043(11) 0.0010(12) -0.0290(13) O3 0.066(2) 0.0509(17) 0.076(2) 0.000 -0.0156(17) 0.000 C1 0.0516(16) 0.0549(16) 0.0373(14) 0.0061(13) 0.0063(12) -0.0007(14) C2 0.0565(18) 0.0607(19) 0.0449(16) 0.0134(14) 0.0052(14) -0.0090(15) C3 0.090(3) 0.103(3) 0.0434(18) 0.0185(19) 0.0103(18) -0.033(2) C4 0.112(3) 0.123(4) 0.0362(17) 0.011(2) 0.0032(19) -0.047(3) C5 0.073(2) 0.081(2) 0.0383(16) 0.0045(16) -0.0030(14) -0.0172(18) C6 0.071(2) 0.0484(16) 0.0525(18) 0.0074(15) 0.0061(15) -0.0107(15) C7 0.118(3) 0.060(2) 0.057(2) 0.0071(17) -0.014(2) -0.021(2) C8 0.082(2) 0.0544(19) 0.069(2) 0.0054(17) -0.0185(19) -0.0023(17) O4 0.61(3) 0.31(3) 0.262(18) 0.163(19) 0.26(2) 0.21(2) O5 1.35(13) 0.222(17) 0.55(5) 0.000 0.63(7) 0.000 _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 Zn N1 2.089(3) 2_556 ? Zn N1 2.089(3) . ? Zn Cl 2.2550(17) 2_556 ? Zn Cl 2.2550(17) . ? N1 C5 1.347(4) . ? N1 C1 1.351(4) . ? N2 C6 1.370(4) . ? N2 C2 1.414(4) . ? N2 H2A 0.8600 . ? O1 C6 1.204(4) . ? O2 C6 1.357(4) . ? O2 C7 1.453(4) . ? O3 C8 1.434(4) . ? O3 C8 1.434(4) 6_565 ? C1 C2 1.406(4) . ? C1 H1A 0.9300 . ? C2 C3 1.411(5) . ? C3 C4 1.383(6) . ? C3 H3A 0.9300 . ? C4 C5 1.393(5) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C7 C8 1.507(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O4 O4 1.33(3) 6_565 ? O4 H402 0.903(19) . ? O4 H401 0.800(17) . ? 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 Zn N1 103.47(14) 2_556 . ? N1 Zn Cl 109.95(10) 2_556 2_556 ? N1 Zn Cl 104.49(9) . 2_556 ? N1 Zn Cl 104.49(9) 2_556 . ? N1 Zn Cl 109.95(10) . . ? Cl Zn Cl 122.95(8) 2_556 . ? C5 N1 C1 119.4(2) . . ? C5 N1 Zn 120.9(2) . . ? C1 N1 Zn 119.74(19) . . ? C6 N2 C2 127.5(3) . . ? C6 N2 H2A 116.2 . . ? C2 N2 H2A 116.2 . . ? C6 O2 C7 115.5(3) . . ? C8 O3 C8 112.8(4) . 6_565 ? N1 C1 C2 122.5(3) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? N2 C2 C1 124.5(3) . . ? N2 C2 C3 118.1(3) . . ? C1 C2 C3 117.4(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? N1 C5 C4 121.5(3) . . ? N1 C5 H5A 119.2 . . ? C4 C5 H5A 119.2 . . ? O1 C6 O2 125.0(3) . . ? O1 C6 N2 125.6(3) . . ? O2 C6 N2 109.4(3) . . ? O2 C7 C8 108.6(3) . . ? O2 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? O2 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? O3 C8 C7 109.4(3) . . ? O3 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? O3 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? O4 O4 H402 42(2) 6_565 . ? O4 O4 H401 137(3) 6_565 . ? H402 O4 H401 145(7) . . ? 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 Zn N1 C5 -119.6(3) 2_556 . . . ? Cl Zn N1 C5 -4.5(3) 2_556 . . . ? Cl Zn N1 C5 129.2(2) . . . . ? N1 Zn N1 C1 61.28(19) 2_556 . . . ? Cl Zn N1 C1 176.38(19) 2_556 . . . ? Cl Zn N1 C1 -49.9(2) . . . . ? C5 N1 C1 C2 0.6(4) . . . . ? Zn N1 C1 C2 179.7(2) . . . . ? C6 N2 C2 C1 -0.3(6) . . . . ? C6 N2 C2 C3 179.9(4) . . . . ? N1 C1 C2 N2 179.7(3) . . . . ? N1 C1 C2 C3 -0.5(5) . . . . ? N2 C2 C3 C4 179.4(4) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C2 C3 C4 C5 1.1(7) . . . . ? C1 N1 C5 C4 0.1(5) . . . . ? Zn N1 C5 C4 -179.0(3) . . . . ? C3 C4 C5 N1 -1.0(7) . . . . ? C7 O2 C6 O1 1.1(6) . . . . ? C7 O2 C6 N2 -176.8(3) . . . . ? C2 N2 C6 O1 0.7(6) . . . . ? C2 N2 C6 O2 178.6(3) . . . . ? C6 O2 C7 C8 -172.7(3) . . . . ? C8 O3 C8 C7 170.1(2) 6_565 . . . ? O2 C7 C8 O3 73.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.533 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.070 ############ data_x2 _database_code_depnum_ccdc_archive 'CCDC 819733' #TrackingRef '- complexes.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H37 Br4 N8 O10.50 Zn2' _chemical_formula_weight 1152.08 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' Zn Zn 0.2839 1.4301 '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' Br Br -0.2901 2.4595 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8072(18) _cell_length_b 10.931(3) _cell_length_c 13.796(3) _cell_angle_alpha 78.771(4) _cell_angle_beta 78.627(3) _cell_angle_gamma 87.263(4) _cell_volume 1132.1(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 569 _exptl_absorpt_coefficient_mu 4.647 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2782 _exptl_absorpt_correction_T_max 0.3896 _exptl_absorpt_process_details SADABS _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 'Bruker APEX II area detector' _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 6152 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4373 _reflns_number_gt 3378 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _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 ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The occupancy parameter of O6 has been refined to 0.25 and the ISOR (with the parameter 0.1) restrain was used to refine its thermal displacement. Two H atoms (H601 and H602) have been located from the difference fourier map and then refined by considering their chemical environments with restraints [O-H = 0.85(2)]. ; _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^)+(0.0429P)^2^+0.2416P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4373 _refine_ls_number_parameters 270 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0905 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn Zn 0.61167(5) 0.66342(4) 0.70573(3) 0.03735(13) Uani 1 1 d . . . Br1 Br 0.91234(5) 0.61902(5) 0.68432(3) 0.06357(15) Uani 1 1 d . . . Br2 Br 0.42158(5) 0.52962(4) 0.83189(3) 0.04871(13) Uani 1 1 d . . . N1 N 0.5368(4) 0.6723(3) 0.5702(2) 0.0384(7) Uani 1 1 d . . . N2 N 0.7266(4) 0.6645(3) 0.3054(2) 0.0464(8) Uani 1 1 d . . . H2A H 0.6880 0.6401 0.2582 0.056 Uiso 1 1 calc R . . N3 N 0.6961(4) 0.9994(3) 0.0823(2) 0.0446(7) Uani 1 1 d . . . H3A H 0.7774 1.0542 0.0636 0.054 Uiso 1 1 calc R . . N4 N 0.4221(4) 1.1595(3) 0.2652(2) 0.0385(7) Uani 1 1 d . . . O1 O 0.9747(4) 0.7368(3) 0.33907(19) 0.0608(8) Uani 1 1 d . . . O2 O 0.9655(3) 0.6845(3) 0.19011(16) 0.0476(7) Uani 1 1 d . . . O3 O 1.1319(3) 0.7558(2) -0.01912(17) 0.0407(6) Uani 1 1 d . . . O4 O 0.8510(3) 0.9196(2) -0.04274(19) 0.0501(7) Uani 1 1 d . . . O5 O 0.6098(4) 0.8183(3) 0.0488(2) 0.0678(9) Uani 1 1 d . . . C1 C 0.6548(4) 0.6751(3) 0.4851(2) 0.0379(8) Uani 1 1 d . . . H1A H 0.7722 0.6842 0.4861 0.046 Uiso 1 1 calc R . . C2 C 0.6070(5) 0.6648(3) 0.3954(2) 0.0366(8) Uani 1 1 d . . . C3 C 0.4317(5) 0.6499(3) 0.3960(3) 0.0420(9) Uani 1 1 d . . . H3B H 0.3959 0.6406 0.3374 0.050 Uiso 1 1 calc R . . C4 C 0.3115(5) 0.6489(4) 0.4825(3) 0.0478(9) Uani 1 1 d . . . H4A H 0.1933 0.6403 0.4834 0.057 Uiso 1 1 calc R . . C5 C 0.3681(5) 0.6609(4) 0.5684(3) 0.0456(9) Uani 1 1 d . . . H5A H 0.2861 0.6611 0.6273 0.055 Uiso 1 1 calc R . . C6 C 0.8980(5) 0.6985(4) 0.2844(2) 0.0422(9) Uani 1 1 d . . . C7 C 1.1491(5) 0.7099(4) 0.1567(3) 0.0483(10) Uani 1 1 d . . . H7A H 1.2148 0.6621 0.2043 0.058 Uiso 1 1 calc R . . H7B H 1.1703 0.7978 0.1518 0.058 Uiso 1 1 calc R . . C8 C 1.2051(5) 0.6744(4) 0.0561(3) 0.0436(9) Uani 1 1 d . . . H8A H 1.3316 0.6769 0.0375 0.052 Uiso 1 1 calc R . . H8B H 1.1690 0.5896 0.0598 0.052 Uiso 1 1 calc R . . C9 C 0.9774(5) 0.7109(4) -0.0411(3) 0.0436(9) Uani 1 1 d . . . H9A H 0.8994 0.6755 0.0209 0.052 Uiso 1 1 calc R . . H9B H 1.0075 0.6465 -0.0812 0.052 Uiso 1 1 calc R . . C10 C 0.8900(6) 0.8185(4) -0.0980(3) 0.0547(11) Uani 1 1 d . . . H10A H 0.9655 0.8487 -0.1623 0.066 Uiso 1 1 calc R . . H10B H 0.7824 0.7904 -0.1113 0.066 Uiso 1 1 calc R . . C11 C 0.7085(5) 0.9036(4) 0.0318(3) 0.0462(9) Uani 1 1 d . . . C12 C 0.3078(5) 1.0707(4) 0.3157(3) 0.0505(10) Uani 1 1 d . . . H12A H 0.2208 1.0885 0.3678 0.061 Uiso 1 1 calc R . . C13 C 0.3169(6) 0.9535(4) 0.2920(3) 0.0576(11) Uani 1 1 d . . . H13A H 0.2367 0.8930 0.3282 0.069 Uiso 1 1 calc R . . C14 C 0.4434(5) 0.9260(4) 0.2156(3) 0.0517(10) Uani 1 1 d . . . H14A H 0.4498 0.8470 0.1993 0.062 Uiso 1 1 calc R . . C15 C 0.5618(4) 1.0165(3) 0.1625(3) 0.0381(8) Uani 1 1 d . . . C16 C 0.5451(4) 1.1324(3) 0.1899(2) 0.0363(8) Uani 1 1 d . . . H16A H 0.6233 1.1944 0.1543 0.044 Uiso 1 1 calc R . . O6 O 0.144(5) -0.004(3) 0.585(3) 0.258(16) Uani 0.25 1 d PDU . . H602 H 0.236(9) -0.009(7) 0.610(7) 0.00(2) Uiso 0.25 1 d PD . . H601 H 0.094(9) 0.060(6) 0.553(7) 0.00(2) Uiso 0.25 1 d PD . . 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 Zn 0.0330(2) 0.0494(3) 0.0293(2) -0.01380(18) 0.00185(16) -0.00319(17) Br1 0.0334(2) 0.0897(4) 0.0626(3) -0.0135(2) -0.00011(19) 0.0072(2) Br2 0.0543(2) 0.0543(3) 0.0342(2) -0.01250(17) 0.00676(16) -0.01422(18) N1 0.0346(16) 0.0494(18) 0.0307(15) -0.0133(13) 0.0017(12) -0.0044(13) N2 0.0359(17) 0.078(2) 0.0286(15) -0.0229(15) 0.0001(13) -0.0109(15) N3 0.0440(18) 0.0405(18) 0.0484(18) -0.0175(15) 0.0034(14) -0.0044(14) N4 0.0371(16) 0.0450(18) 0.0325(15) -0.0094(13) -0.0012(13) -0.0051(13) O1 0.0549(17) 0.096(2) 0.0361(14) -0.0286(15) 0.0023(13) -0.0301(16) O2 0.0370(14) 0.0789(19) 0.0272(12) -0.0158(12) 0.0013(10) -0.0102(13) O3 0.0393(14) 0.0471(15) 0.0330(13) -0.0023(11) -0.0045(11) -0.0052(11) O4 0.0549(17) 0.0499(16) 0.0455(15) -0.0173(13) -0.0036(13) 0.0071(13) O5 0.0571(19) 0.064(2) 0.088(2) -0.0417(17) 0.0013(16) -0.0120(16) C1 0.0302(18) 0.051(2) 0.0325(18) -0.0112(16) -0.0005(14) -0.0055(15) C2 0.040(2) 0.043(2) 0.0271(17) -0.0103(15) -0.0016(14) -0.0040(15) C3 0.044(2) 0.053(2) 0.0305(18) -0.0095(17) -0.0092(16) -0.0047(17) C4 0.0293(19) 0.068(3) 0.044(2) -0.0095(19) -0.0038(16) -0.0043(17) C5 0.033(2) 0.062(3) 0.038(2) -0.0112(18) 0.0031(16) 0.0014(17) C6 0.046(2) 0.053(2) 0.0272(18) -0.0104(17) -0.0022(16) -0.0060(17) C7 0.036(2) 0.073(3) 0.0342(19) -0.0095(19) -0.0026(16) -0.0089(19) C8 0.0342(19) 0.054(2) 0.039(2) -0.0075(18) 0.0006(15) -0.0012(17) C9 0.046(2) 0.048(2) 0.040(2) -0.0198(17) -0.0061(17) 0.0003(17) C10 0.061(3) 0.070(3) 0.041(2) -0.028(2) -0.0159(19) 0.018(2) C11 0.043(2) 0.045(2) 0.055(2) -0.0167(19) -0.0131(19) 0.0048(18) C12 0.042(2) 0.060(3) 0.041(2) -0.0038(19) 0.0077(17) -0.0085(19) C13 0.053(3) 0.044(2) 0.064(3) -0.003(2) 0.012(2) -0.0138(19) C14 0.051(2) 0.037(2) 0.063(3) -0.0081(19) -0.002(2) -0.0037(18) C15 0.037(2) 0.038(2) 0.0398(19) -0.0083(16) -0.0065(16) 0.0005(15) C16 0.0331(18) 0.040(2) 0.0340(18) -0.0089(15) 0.0002(14) -0.0051(15) O6 0.259(18) 0.257(18) 0.254(18) -0.068(10) -0.021(10) -0.010(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn N4 2.047(3) 2_676 ? Zn N1 2.050(3) . ? Zn Br1 2.3466(8) . ? Zn Br2 2.3597(6) . ? N1 C5 1.334(4) . ? N1 C1 1.338(4) . ? N2 C6 1.365(4) . ? N2 C2 1.400(4) . ? N2 H2A 0.8600 . ? N3 C11 1.357(5) . ? N3 C15 1.400(4) . ? N3 H3A 0.8600 . ? N4 C16 1.337(4) . ? N4 C12 1.341(4) . ? N4 Zn 2.047(3) 2_676 ? O1 C6 1.195(4) . ? O2 C6 1.339(4) . ? O2 C7 1.439(4) . ? O3 C8 1.421(4) . ? O3 C9 1.430(4) . ? O4 C11 1.351(5) . ? O4 C10 1.450(4) . ? O5 C11 1.196(5) . ? C1 C2 1.386(4) . ? C1 H1A 0.9300 . ? C2 C3 1.384(5) . ? C3 C4 1.364(5) . ? C3 H3B 0.9300 . ? C4 C5 1.375(5) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C7 C8 1.491(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.497(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.378(6) . ? C12 H12A 0.9300 . ? C13 C14 1.365(6) . ? C13 H13A 0.9300 . ? C14 C15 1.382(5) . ? C14 H14A 0.9300 . ? C15 C16 1.384(5) . ? C16 H16A 0.9300 . ? O6 H602 0.845(14) . ? O6 H601 0.872(14) . ? 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 Zn N1 105.32(12) 2_676 . ? N4 Zn Br1 106.98(8) 2_676 . ? N1 Zn Br1 108.21(8) . . ? N4 Zn Br2 108.42(8) 2_676 . ? N1 Zn Br2 109.10(8) . . ? Br1 Zn Br2 118.07(3) . . ? C5 N1 C1 119.0(3) . . ? C5 N1 Zn 119.2(2) . . ? C1 N1 Zn 121.3(2) . . ? C6 N2 C2 127.2(3) . . ? C6 N2 H2A 116.4 . . ? C2 N2 H2A 116.4 . . ? C11 N3 C15 125.4(3) . . ? C11 N3 H3A 117.3 . . ? C15 N3 H3A 117.3 . . ? C16 N4 C12 118.5(3) . . ? C16 N4 Zn 121.6(2) . 2_676 ? C12 N4 Zn 119.6(3) . 2_676 ? C6 O2 C7 115.7(3) . . ? C8 O3 C9 114.9(3) . . ? C11 O4 C10 115.4(3) . . ? N1 C1 C2 121.9(3) . . ? N1 C1 H1A 119.1 . . ? C2 C1 H1A 119.1 . . ? C3 C2 C1 118.1(3) . . ? C3 C2 N2 118.3(3) . . ? C1 C2 N2 123.6(3) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3B 120.0 . . ? C2 C3 H3B 120.0 . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? N1 C5 C4 122.2(3) . . ? N1 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? O1 C6 O2 125.4(3) . . ? O1 C6 N2 126.5(3) . . ? O2 C6 N2 108.0(3) . . ? O2 C7 C8 108.1(3) . . ? O2 C7 H7A 110.1 . . ? C8 C7 H7A 110.1 . . ? O2 C7 H7B 110.1 . . ? C8 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? O3 C8 C7 111.5(3) . . ? O3 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? O3 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? O3 C9 C10 108.1(3) . . ? O3 C9 H9A 110.1 . . ? C10 C9 H9A 110.1 . . ? O3 C9 H9B 110.1 . . ? C10 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? O4 C10 C9 111.8(3) . . ? O4 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? O4 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? O5 C11 O4 124.5(4) . . ? O5 C11 N3 126.4(4) . . ? O4 C11 N3 109.1(3) . . ? N4 C12 C13 121.3(4) . . ? N4 C12 H12A 119.4 . . ? C13 C12 H12A 119.4 . . ? C14 C13 C12 120.0(4) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C13 C14 C15 119.4(4) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C14 C15 C16 117.6(3) . . ? C14 C15 N3 124.5(3) . . ? C16 C15 N3 117.9(3) . . ? N4 C16 C15 123.2(3) . . ? N4 C16 H16A 118.4 . . ? C15 C16 H16A 118.4 . . ? H602 O6 H601 131(4) . . ? 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 Zn N1 C5 -84.8(3) 2_676 . . . ? Br1 Zn N1 C5 161.0(3) . . . . ? Br2 Zn N1 C5 31.4(3) . . . . ? N4 Zn N1 C1 102.8(3) 2_676 . . . ? Br1 Zn N1 C1 -11.3(3) . . . . ? Br2 Zn N1 C1 -141.0(3) . . . . ? C5 N1 C1 C2 -0.9(5) . . . . ? Zn N1 C1 C2 171.5(3) . . . . ? N1 C1 C2 C3 -0.8(6) . . . . ? N1 C1 C2 N2 -178.5(3) . . . . ? C6 N2 C2 C3 167.9(4) . . . . ? C6 N2 C2 C1 -14.4(6) . . . . ? C1 C2 C3 C4 1.7(6) . . . . ? N2 C2 C3 C4 179.5(4) . . . . ? C2 C3 C4 C5 -1.0(6) . . . . ? C1 N1 C5 C4 1.6(6) . . . . ? Zn N1 C5 C4 -170.9(3) . . . . ? C3 C4 C5 N1 -0.6(6) . . . . ? C7 O2 C6 O1 4.7(6) . . . . ? C7 O2 C6 N2 -176.8(3) . . . . ? C2 N2 C6 O1 -1.4(7) . . . . ? C2 N2 C6 O2 -179.9(4) . . . . ? C6 O2 C7 C8 173.0(3) . . . . ? C9 O3 C8 C7 -97.2(4) . . . . ? O2 C7 C8 O3 68.9(4) . . . . ? C8 O3 C9 C10 164.4(3) . . . . ? C11 O4 C10 C9 -78.5(4) . . . . ? O3 C9 C10 O4 -56.7(4) . . . . ? C10 O4 C11 O5 -5.7(5) . . . . ? C10 O4 C11 N3 174.9(3) . . . . ? C15 N3 C11 O5 -1.5(6) . . . . ? C15 N3 C11 O4 177.9(3) . . . . ? C16 N4 C12 C13 0.7(6) . . . . ? Zn N4 C12 C13 174.1(3) 2_676 . . . ? N4 C12 C13 C14 -0.3(7) . . . . ? C12 C13 C14 C15 0.1(7) . . . . ? C13 C14 C15 C16 -0.3(6) . . . . ? C13 C14 C15 N3 -179.5(4) . . . . ? C11 N3 C15 C14 14.4(6) . . . . ? C11 N3 C15 C16 -164.9(3) . . . . ? C12 N4 C16 C15 -1.0(5) . . . . ? Zn N4 C16 C15 -174.1(3) 2_676 . . . ? C14 C15 C16 N4 0.7(5) . . . . ? N3 C15 C16 N4 -180.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.756 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.075 ############ data_x4 _database_code_depnum_ccdc_archive 'CCDC 819734' #TrackingRef '- complexes.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 Br4 N8 O12 Zn2' _chemical_formula_weight 1231.17 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.1577(12) _cell_length_b 21.085(5) _cell_length_c 21.538(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.032(4) _cell_angle_gamma 90.00 _cell_volume 2333.2(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.752 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 4.518 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2931 _exptl_absorpt_correction_T_max 0.4230 _exptl_absorpt_process_details SADABS _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 'Bruker APEX II area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11515 _diffrn_reflns_av_R_equivalents 0.0858 _diffrn_reflns_av_sigmaI/netI 0.0976 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4138 _reflns_number_gt 2514 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The restraints were used to refine the flexible chains to obtain credible structures. The DFIX ([C-C = 1.54(2)]) instruction has been taken on C9 and C10, and four DELU restraints with parameter 0.02 together with four SIMU restraints with parameter 0.02 have been used on C9, C10, O3 and O4 to refine their thermal displacements. ; _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^)+(0.0479P)^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 4138 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1054 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.890 _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 Br1 Br 1.50688(10) 0.17001(3) 0.80022(2) 0.04568(18) Uani 1 1 d . . . Br2 Br 1.29572(12) 0.13334(3) 0.60558(3) 0.0603(2) Uani 1 1 d . . . Zn1 Zn 1.21651(12) 0.15477(3) 0.71064(3) 0.0413(2) Uani 1 1 d . . . O1 O -0.3025(8) 0.0250(2) 1.11168(18) 0.0693(13) Uani 1 1 d . . . O2 O -0.0349(8) 0.0642(2) 1.04508(17) 0.0600(11) Uani 1 1 d . . . O3 O -0.0678(12) 0.1835(2) 0.9851(2) 0.1035(19) Uani 1 1 d . . . O4 O 0.1793(8) 0.3275(2) 0.9254(2) 0.0664(12) Uani 1 1 d . . . O5 O 0.6075(7) 0.40045(19) 0.89074(19) 0.0575(11) Uani 1 1 d . . . O6 O 0.3548(8) 0.3903(2) 0.79985(18) 0.0602(11) Uani 1 1 d . . . N1 N 0.9888(8) 0.2355(2) 0.7044(2) 0.0445(11) Uani 1 1 d . . . N2 N 0.0003(7) -0.0777(2) 1.26576(19) 0.0356(10) Uani 1 1 d . . . N3 N 0.7664(8) 0.3499(2) 0.8136(2) 0.0437(11) Uani 1 1 d . . . H3B H 0.9032 0.3498 0.8395 0.052 Uiso 1 1 calc R . . N4 N 0.1369(8) 0.0196(2) 1.13087(19) 0.0454(12) Uani 1 1 d . . . H4B H 0.2799 0.0263 1.1142 0.054 Uiso 1 1 calc R . . C1 C -0.0163(9) -0.0524(2) 1.2083(2) 0.0377(13) Uani 1 1 d . . . H1A H -0.1475 -0.0660 1.1790 0.045 Uiso 1 1 calc R . . C2 C 0.1897(10) -0.0574(3) 1.3073(2) 0.0472(14) Uani 1 1 d . . . H2A H 0.1991 -0.0737 1.3476 0.057 Uiso 1 1 calc R . . C3 C 0.3721(10) -0.0131(3) 1.2925(3) 0.0487(15) Uani 1 1 d . . . H3A H 0.5063 -0.0012 1.3218 0.058 Uiso 1 1 calc R . . C4 C 0.3518(10) 0.0130(3) 1.2335(3) 0.0450(14) Uani 1 1 d . . . H4A H 0.4700 0.0435 1.2227 0.054 Uiso 1 1 calc R . . C5 C 0.1560(9) -0.0066(3) 1.1915(2) 0.0380(13) Uani 1 1 d . . . C6 C -0.0862(12) 0.0351(3) 1.0969(3) 0.0467(14) Uani 1 1 d . . . C7 C -0.2560(13) 0.0856(3) 1.0054(3) 0.074(2) Uani 1 1 d . . . H7A H -0.3752 0.1086 1.0296 0.088 Uiso 1 1 calc R . . H7B H -0.3477 0.0497 0.9858 0.088 Uiso 1 1 calc R . . C8 C -0.1579(18) 0.1276(4) 0.9576(3) 0.097(3) Uani 1 1 d . . . H8A H -0.0181 0.1066 0.9383 0.116 Uiso 1 1 calc R . . H8B H -0.2966 0.1366 0.9254 0.116 Uiso 1 1 calc R . . C9 C 0.007(2) 0.2297(4) 0.9387(4) 0.131(4) Uani 1 1 d . . . H9A H 0.1271 0.2102 0.9121 0.157 Uiso 1 1 calc R . . H9B H -0.1455 0.2435 0.9128 0.157 Uiso 1 1 calc R . . C10 C 0.117(2) 0.2779(5) 0.9672(4) 0.135(4) Uani 1 1 d . . . H10A H 0.2758 0.2640 0.9909 0.162 Uiso 1 1 calc R . . H10B H 0.0019 0.2947 0.9964 0.162 Uiso 1 1 calc R . . C11 C 0.2899(14) 0.3794(4) 0.9612(3) 0.077(2) Uani 1 1 d . . . H11A H 0.4289 0.3643 0.9908 0.092 Uiso 1 1 calc R . . H11B H 0.1581 0.3990 0.9843 0.092 Uiso 1 1 calc R . . C12 C 0.3914(12) 0.4254(3) 0.9197(3) 0.0695(19) Uani 1 1 d . . . H12A H 0.2554 0.4374 0.8879 0.083 Uiso 1 1 calc R . . H12B H 0.4452 0.4632 0.9431 0.083 Uiso 1 1 calc R . . C13 C 0.5528(12) 0.3805(3) 0.8305(3) 0.0467(15) Uani 1 1 d . . . C14 C 0.7785(10) 0.3187(3) 0.7569(2) 0.0388(13) Uani 1 1 d . . . C15 C 0.9640(10) 0.2711(3) 0.7548(2) 0.0410(13) Uani 1 1 d . . . H15A H 1.0764 0.2637 0.7902 0.049 Uiso 1 1 calc R . . C16 C 0.8322(11) 0.2479(3) 0.6527(2) 0.0532(15) Uani 1 1 d . . . H16A H 0.8478 0.2237 0.6171 0.064 Uiso 1 1 calc R . . C17 C 0.6495(12) 0.2954(3) 0.6511(3) 0.0607(18) Uani 1 1 d . . . H17A H 0.5453 0.3034 0.6145 0.073 Uiso 1 1 calc R . . C18 C 0.6204(11) 0.3310(3) 0.7032(3) 0.0520(15) Uani 1 1 d . . . H18A H 0.4960 0.3630 0.7024 0.062 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 Br1 0.0456(3) 0.0482(4) 0.0420(3) 0.0042(3) -0.0033(2) -0.0044(3) Br2 0.0625(4) 0.0858(5) 0.0331(3) 0.0061(3) 0.0066(3) 0.0039(4) Zn1 0.0459(4) 0.0440(4) 0.0337(4) 0.0058(3) 0.0018(3) -0.0020(3) O1 0.049(2) 0.094(4) 0.066(3) 0.036(3) 0.010(2) 0.001(2) O2 0.068(3) 0.069(3) 0.043(2) 0.025(2) 0.001(2) -0.013(2) O3 0.183(6) 0.061(4) 0.064(3) 0.020(3) -0.002(3) -0.028(4) O4 0.074(3) 0.066(3) 0.060(3) 0.021(3) 0.010(2) -0.006(2) O5 0.050(2) 0.062(3) 0.060(3) -0.010(2) 0.001(2) 0.000(2) O6 0.046(2) 0.067(3) 0.065(3) 0.001(2) -0.008(2) 0.005(2) N1 0.047(3) 0.044(3) 0.041(3) 0.011(2) -0.002(2) -0.004(2) N2 0.035(2) 0.036(3) 0.034(3) 0.002(2) -0.002(2) 0.000(2) N3 0.036(2) 0.046(3) 0.047(3) 0.002(2) -0.007(2) 0.001(2) N4 0.043(3) 0.052(3) 0.042(3) 0.010(2) 0.003(2) -0.004(2) C1 0.039(3) 0.039(3) 0.034(3) 0.001(3) -0.002(2) -0.002(3) C2 0.046(3) 0.059(4) 0.037(3) 0.001(3) -0.001(3) 0.008(3) C3 0.040(3) 0.052(4) 0.053(4) -0.011(3) -0.005(3) -0.009(3) C4 0.039(3) 0.044(4) 0.053(4) -0.005(3) 0.005(3) -0.005(3) C5 0.034(3) 0.035(3) 0.045(3) -0.001(3) 0.002(3) 0.000(3) C6 0.061(4) 0.037(4) 0.042(3) 0.011(3) 0.007(3) -0.005(3) C7 0.092(5) 0.074(5) 0.053(4) 0.022(4) -0.004(4) -0.019(4) C8 0.144(7) 0.085(6) 0.056(5) 0.020(4) -0.015(5) -0.026(6) C9 0.230(12) 0.073(7) 0.081(6) 0.021(5) -0.029(7) -0.046(7) C10 0.207(11) 0.107(9) 0.094(7) 0.024(6) 0.035(7) -0.038(8) C11 0.075(5) 0.100(6) 0.056(5) 0.004(4) 0.003(4) 0.009(5) C12 0.069(4) 0.065(5) 0.074(5) -0.020(4) 0.003(4) 0.004(4) C13 0.050(4) 0.035(4) 0.055(4) 0.010(3) 0.003(3) -0.005(3) C14 0.036(3) 0.039(4) 0.041(3) 0.010(3) -0.001(3) -0.007(3) C15 0.049(3) 0.042(4) 0.031(3) 0.008(3) -0.005(2) -0.005(3) C16 0.067(4) 0.055(4) 0.035(3) 0.004(3) -0.009(3) 0.002(3) C17 0.071(4) 0.064(5) 0.043(4) 0.008(3) -0.025(3) 0.015(4) C18 0.057(4) 0.044(4) 0.054(4) 0.006(3) -0.003(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Zn1 2.3583(9) . ? Br2 Zn1 2.3776(9) . ? Zn1 N2 2.062(4) 3_657 ? Zn1 N1 2.065(5) . ? O1 C6 1.205(6) . ? O2 C6 1.321(6) . ? O2 C7 1.436(7) . ? O3 C8 1.382(8) . ? O3 C9 1.472(9) . ? O4 C11 1.429(8) . ? O4 C10 1.433(8) . ? O5 C13 1.370(6) . ? O5 C12 1.425(7) . ? O6 C13 1.185(6) . ? N1 C15 1.336(6) . ? N1 C16 1.342(6) . ? N2 C2 1.336(6) . ? N2 C1 1.344(5) . ? N2 Zn1 2.062(4) 3_657 ? N3 C13 1.353(7) . ? N3 C14 1.394(6) . ? N3 H3B 0.8600 . ? N4 C6 1.348(7) . ? N4 C5 1.414(6) . ? N4 H4B 0.8600 . ? C1 C5 1.381(7) . ? C1 H1A 0.9300 . ? C2 C3 1.382(7) . ? C2 H2A 0.9300 . ? C3 C4 1.380(7) . ? C3 H3A 0.9300 . ? C4 C5 1.360(7) . ? C4 H4A 0.9300 . ? C7 C8 1.481(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.291(10) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.447(9) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C18 1.381(7) . ? C14 C15 1.390(7) . ? C15 H15A 0.9300 . ? C16 C17 1.374(8) . ? C16 H16A 0.9300 . ? C17 C18 1.369(7) . ? C17 H17A 0.9300 . ? C18 H18A 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 N2 Zn1 N1 110.37(16) 3_657 . ? N2 Zn1 Br1 103.00(12) 3_657 . ? N1 Zn1 Br1 104.95(13) . . ? N2 Zn1 Br2 103.12(12) 3_657 . ? N1 Zn1 Br2 103.79(12) . . ? Br1 Zn1 Br2 130.89(4) . . ? C6 O2 C7 116.2(5) . . ? C8 O3 C9 111.9(6) . . ? C11 O4 C10 108.7(6) . . ? C13 O5 C12 115.1(5) . . ? C15 N1 C16 118.0(5) . . ? C15 N1 Zn1 120.3(4) . . ? C16 N1 Zn1 120.9(4) . . ? C2 N2 C1 118.3(5) . . ? C2 N2 Zn1 117.9(4) . 3_657 ? C1 N2 Zn1 123.3(3) . 3_657 ? C13 N3 C14 124.1(5) . . ? C13 N3 H3B 117.9 . . ? C14 N3 H3B 117.9 . . ? C6 N4 C5 125.7(4) . . ? C6 N4 H4B 117.2 . . ? C5 N4 H4B 117.2 . . ? N2 C1 C5 121.9(5) . . ? N2 C1 H1A 119.0 . . ? C5 C1 H1A 119.0 . . ? N2 C2 C3 122.3(5) . . ? N2 C2 H2A 118.9 . . ? C3 C2 H2A 118.9 . . ? C4 C3 C2 118.9(5) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C5 C4 C3 118.9(5) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 C1 119.7(5) . . ? C4 C5 N4 118.9(5) . . ? C1 C5 N4 121.4(5) . . ? O1 C6 O2 124.3(6) . . ? O1 C6 N4 125.4(5) . . ? O2 C6 N4 110.2(5) . . ? O2 C7 C8 107.4(6) . . ? O2 C7 H7A 110.2 . . ? C8 C7 H7A 110.2 . . ? O2 C7 H7B 110.2 . . ? C8 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? O3 C8 C7 109.5(6) . . ? O3 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? O3 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C10 C9 O3 109.3(8) . . ? C10 C9 H9A 109.8 . . ? O3 C9 H9A 109.8 . . ? C10 C9 H9B 109.8 . . ? O3 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? C9 C10 O4 112.8(8) . . ? C9 C10 H10A 109.0 . . ? O4 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? O4 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? O4 C11 C12 109.3(5) . . ? O4 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? O4 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? O5 C12 C11 111.2(6) . . ? O5 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? O5 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? O6 C13 N3 128.0(6) . . ? O6 C13 O5 124.7(6) . . ? N3 C13 O5 107.2(5) . . ? C18 C14 C15 117.8(5) . . ? C18 C14 N3 125.2(5) . . ? C15 C14 N3 117.0(5) . . ? N1 C15 C14 123.2(5) . . ? N1 C15 H15A 118.4 . . ? C14 C15 H15A 118.4 . . ? N1 C16 C17 121.7(5) . . ? N1 C16 H16A 119.1 . . ? C17 C16 H16A 119.1 . . ? C18 C17 C16 120.2(5) . . ? C18 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? C17 C18 C14 119.0(6) . . ? C17 C18 H18A 120.5 . . ? C14 C18 H18A 120.5 . . ? 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 N2 Zn1 N1 C15 88.2(4) 3_657 . . . ? Br1 Zn1 N1 C15 -22.1(4) . . . . ? Br2 Zn1 N1 C15 -161.9(4) . . . . ? N2 Zn1 N1 C16 -81.4(4) 3_657 . . . ? Br1 Zn1 N1 C16 168.3(4) . . . . ? Br2 Zn1 N1 C16 28.5(4) . . . . ? C2 N2 C1 C5 0.1(7) . . . . ? Zn1 N2 C1 C5 -170.8(4) 3_657 . . . ? C1 N2 C2 C3 -2.1(8) . . . . ? Zn1 N2 C2 C3 169.3(4) 3_657 . . . ? N2 C2 C3 C4 2.7(8) . . . . ? C2 C3 C4 C5 -1.3(8) . . . . ? C3 C4 C5 C1 -0.6(8) . . . . ? C3 C4 C5 N4 -179.3(5) . . . . ? N2 C1 C5 C4 1.2(8) . . . . ? N2 C1 C5 N4 179.9(4) . . . . ? C6 N4 C5 C4 -141.2(5) . . . . ? C6 N4 C5 C1 40.1(8) . . . . ? C7 O2 C6 O1 1.2(9) . . . . ? C7 O2 C6 N4 -177.7(5) . . . . ? C5 N4 C6 O1 -5.1(9) . . . . ? C5 N4 C6 O2 173.8(5) . . . . ? C6 O2 C7 C8 168.7(6) . . . . ? C9 O3 C8 C7 -174.1(7) . . . . ? O2 C7 C8 O3 -70.1(8) . . . . ? C8 O3 C9 C10 -172.7(10) . . . . ? O3 C9 C10 O4 -175.6(7) . . . . ? C11 O4 C10 C9 177.7(9) . . . . ? C10 O4 C11 C12 170.9(7) . . . . ? C13 O5 C12 C11 101.6(6) . . . . ? O4 C11 C12 O5 -66.7(7) . . . . ? C14 N3 C13 O6 -6.6(9) . . . . ? C14 N3 C13 O5 175.0(4) . . . . ? C12 O5 C13 O6 10.5(8) . . . . ? C12 O5 C13 N3 -171.0(5) . . . . ? C13 N3 C14 C18 23.0(8) . . . . ? C13 N3 C14 C15 -156.6(5) . . . . ? C16 N1 C15 C14 2.3(8) . . . . ? Zn1 N1 C15 C14 -167.6(4) . . . . ? C18 C14 C15 N1 -2.7(8) . . . . ? N3 C14 C15 N1 176.9(4) . . . . ? C15 N1 C16 C17 -0.4(8) . . . . ? Zn1 N1 C16 C17 169.4(5) . . . . ? N1 C16 C17 C18 -1.0(10) . . . . ? C16 C17 C18 C14 0.5(9) . . . . ? C15 C14 C18 C17 1.2(8) . . . . ? N3 C14 C18 C17 -178.3(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 N4 H4B O1 0.86 2.16 2.959(6) 154.5 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.586 _refine_diff_density_min -0.647 _refine_diff_density_rms 0.124 ############ data_X5 _database_code_depnum_ccdc_archive 'CCDC 819735' #TrackingRef '- complexes.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 Br2 N4 O4 Zn' _chemical_formula_weight 541.51 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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 18.484(5) _cell_length_b 11.438(3) _cell_length_c 9.597(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2029.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.773 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 5.175 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3059 _exptl_absorpt_correction_T_max 0.5107 _exptl_absorpt_process_details SADABS _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 'Bruker APEX II area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13491 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.72 _reflns_number_total 3551 _reflns_number_gt 2243 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0630P)^2^+7.9199P] 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 0.45(3) _refine_ls_number_reflns 3551 _refine_ls_number_parameters 236 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1074 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1367 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Zn Zn 0.12482(6) 0.35791(11) 0.29161(18) 0.0662(4) Uani 1 1 d . . . Br1 Br 0.07992(8) 0.33106(14) 0.0647(2) 0.0984(6) Uani 1 1 d . . . Br2 Br 0.05818(8) 0.30728(14) 0.4978(2) 0.1047(7) Uani 1 1 d . . . N1 N 0.1557(4) 0.5284(7) 0.3230(10) 0.054(3) Uani 1 1 d . . . N2 N 0.1031(4) 0.7661(7) 0.5518(10) 0.046(2) Uani 1 1 d . . . H2 H 0.0639 0.7332 0.5797 0.056 Uiso 1 1 calc R . . N3 N -0.1204(4) 1.2256(7) 0.5376(10) 0.049(2) Uani 1 1 d . . . H3 H -0.0837 1.2710 0.5491 0.059 Uiso 1 1 calc R . . N4 N -0.2807(4) 1.2336(7) 0.3127(10) 0.043(2) Uani 1 1 d . . . C1 C 0.1210(5) 0.5939(9) 0.4153(12) 0.051(3) Uani 1 1 d . . . H1 H 0.0798 0.5637 0.4578 0.061 Uiso 1 1 calc R . . C2 C 0.1435(5) 0.7057(8) 0.4514(10) 0.039(2) Uani 1 1 d . . . C3 C 0.2068(5) 0.7490(10) 0.3902(11) 0.051(3) Uani 1 1 d . . . H3A H 0.2253 0.8215 0.4154 0.061 Uiso 1 1 calc R . . C4 C 0.2413(5) 0.6797(8) 0.2900(15) 0.053(3) Uani 1 1 d . . . H4 H 0.2821 0.7078 0.2443 0.063 Uiso 1 1 calc R . . C5 C 0.2151(6) 0.5701(9) 0.2590(12) 0.055(3) Uani 1 1 d . . . H5 H 0.2387 0.5243 0.1931 0.066 Uiso 1 1 calc R . . C6 C 0.1192(5) 0.8699(9) 0.6087(11) 0.042(2) Uani 1 1 d . . . C7 C 0.0747(5) 1.0076(8) 0.7742(14) 0.051(3) Uani 1 1 d . . . H7A H 0.1179 1.0082 0.8318 0.061 Uiso 1 1 calc R . . H7B H 0.0784 1.0708 0.7072 0.061 Uiso 1 1 calc R . . C8 C 0.0103(5) 1.0230(9) 0.8609(11) 0.045(2) Uani 1 1 d . . . H8A H 0.0126 1.0993 0.9048 0.054 Uiso 1 1 calc R . . H8B H 0.0110 0.9648 0.9343 0.054 Uiso 1 1 calc R . . C9 C -0.0611(5) 1.0132(8) 0.7832(13) 0.043(2) Uani 1 1 d . . . H9A H -0.0622 0.9431 0.7264 0.051 Uiso 1 1 calc R . . H9B H -0.1014 1.0111 0.8478 0.051 Uiso 1 1 calc R . . C10 C -0.1215(5) 1.1268(9) 0.6157(11) 0.042(2) Uani 1 1 d . . . C11 C -0.1714(5) 1.2618(8) 0.4414(11) 0.039(2) Uani 1 1 d . . . C12 C -0.2325(5) 1.1988(8) 0.4097(11) 0.041(2) Uani 1 1 d . . . H12 H -0.2410 1.1292 0.4570 0.050 Uiso 1 1 calc R . . C13 C -0.2692(6) 1.3322(9) 0.2461(12) 0.055(3) Uani 1 1 d . . . H13 H -0.3020 1.3559 0.1783 0.066 Uiso 1 1 calc R . . C14 C -0.2097(6) 1.4016(8) 0.2740(14) 0.057(3) Uani 1 1 d . . . H14 H -0.2035 1.4720 0.2270 0.069 Uiso 1 1 calc R . . C15 C -0.1591(6) 1.3659(9) 0.3727(12) 0.055(3) Uani 1 1 d . . . H15 H -0.1183 1.4108 0.3917 0.066 Uiso 1 1 calc R . . O1 O 0.1702(4) 0.9305(7) 0.5827(8) 0.060(2) Uani 1 1 d . . . O2 O 0.0683(4) 0.8965(6) 0.7024(8) 0.0520(18) Uani 1 1 d . . . O3 O -0.0643(3) 1.1183(6) 0.6957(8) 0.0500(18) Uani 1 1 d . . . O4 O -0.1705(4) 1.0558(6) 0.6131(8) 0.061(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 Zn 0.0338(5) 0.0529(7) 0.1118(12) -0.0198(10) -0.0080(8) 0.0005(6) Br1 0.0804(9) 0.0898(10) 0.1250(15) -0.0145(10) -0.0503(10) -0.0054(8) Br2 0.0694(8) 0.0892(10) 0.1554(17) 0.0033(11) 0.0413(10) -0.0152(7) N1 0.036(4) 0.048(4) 0.078(8) -0.012(5) 0.005(5) 0.011(4) N2 0.038(4) 0.044(5) 0.058(6) -0.010(5) 0.011(4) 0.000(4) N3 0.041(4) 0.041(5) 0.066(7) 0.019(5) 0.000(5) -0.008(4) N4 0.035(4) 0.046(4) 0.048(6) 0.004(4) 0.000(4) 0.010(3) C1 0.026(4) 0.055(6) 0.072(8) -0.018(6) 0.010(5) -0.001(5) C2 0.034(5) 0.041(5) 0.043(7) -0.004(5) 0.005(4) 0.012(4) C3 0.042(6) 0.065(7) 0.046(7) -0.006(6) 0.002(5) -0.006(5) C4 0.046(5) 0.060(6) 0.052(6) 0.000(7) 0.012(6) 0.007(5) C5 0.050(6) 0.053(6) 0.063(9) -0.011(6) 0.003(5) 0.008(5) C6 0.034(5) 0.057(7) 0.036(6) -0.003(5) -0.002(5) 0.014(5) C7 0.037(5) 0.058(6) 0.058(7) 0.012(7) -0.009(5) 0.004(5) C8 0.055(6) 0.049(5) 0.032(6) 0.003(5) -0.011(5) 0.005(5) C9 0.036(5) 0.056(5) 0.036(5) 0.007(6) 0.003(5) 0.006(4) C10 0.035(5) 0.043(6) 0.046(7) -0.003(5) 0.009(5) 0.003(5) C11 0.036(5) 0.035(5) 0.047(7) 0.017(5) 0.001(4) 0.004(4) C12 0.036(5) 0.039(5) 0.048(7) 0.018(5) 0.003(5) -0.001(4) C13 0.043(6) 0.045(6) 0.076(10) 0.017(6) -0.004(5) 0.014(5) C14 0.064(7) 0.039(5) 0.069(8) 0.019(6) 0.001(6) -0.003(5) C15 0.047(6) 0.050(6) 0.068(8) 0.014(6) -0.004(6) 0.000(5) O1 0.046(4) 0.073(5) 0.061(5) -0.022(4) 0.002(4) -0.010(4) O2 0.050(4) 0.048(4) 0.058(5) -0.012(4) 0.010(4) 0.003(3) O3 0.039(4) 0.052(4) 0.059(5) 0.010(4) -0.006(4) 0.002(3) O4 0.053(4) 0.055(4) 0.075(6) 0.032(4) -0.021(4) -0.012(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 Zn N4 2.047(7) 3_565 ? Zn N1 2.055(8) . ? Zn Br1 2.351(2) . ? Zn Br2 2.402(2) . ? N1 C1 1.326(12) . ? N1 C5 1.344(13) . ? N2 C6 1.341(12) . ? N2 C2 1.402(12) . ? N2 H2 0.8600 . ? N3 C10 1.357(12) . ? N3 C11 1.383(12) . ? N3 H3 0.8600 . ? N4 C13 1.313(12) . ? N4 C12 1.348(12) . ? N4 Zn 2.047(7) 3_465 ? C1 C2 1.388(14) . ? C1 H1 0.9300 . ? C2 C3 1.399(13) . ? C3 C4 1.400(15) . ? C3 H3A 0.9300 . ? C4 C5 1.378(14) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 O1 1.196(11) 1 ? C6 O1 1.196(11) . ? C6 O2 1.336(11) . ? C7 C8 1.464(15) . ? C7 O2 1.451(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.520(13) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O3 1.467(12) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O4 1.217(11) 1 ? C10 O4 1.217(11) . ? C10 O3 1.310(11) . ? C11 C15 1.381(13) . ? C11 C12 1.374(12) . ? C12 H12 0.9300 . ? C13 C14 1.383(14) . ? C13 H13 0.9300 . ? C14 C15 1.392(15) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O1 O1 0.00(2) 1 ? O4 O4 0.00(3) 1 ? 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 Zn N1 103.5(3) 3_565 . ? N4 Zn Br1 109.0(3) 3_565 . ? N1 Zn Br1 111.0(3) . . ? N4 Zn Br2 103.5(3) 3_565 . ? N1 Zn Br2 104.5(3) . . ? Br1 Zn Br2 123.42(8) . . ? C1 N1 C5 120.0(9) . . ? C1 N1 Zn 120.0(7) . . ? C5 N1 Zn 119.8(7) . . ? C6 N2 C2 126.8(9) . . ? C6 N2 H2 116.6 . . ? C2 N2 H2 116.6 . . ? C10 N3 C11 127.4(8) . . ? C10 N3 H3 116.3 . . ? C11 N3 H3 116.3 . . ? C13 N4 C12 118.9(8) . . ? C13 N4 Zn 121.9(7) . 3_465 ? C12 N4 Zn 118.7(6) . 3_465 ? N1 C1 C2 122.8(9) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 N2 117.7(8) . . ? C1 C2 C3 118.2(9) . . ? N2 C2 C3 124.0(9) . . ? C4 C3 C2 118.0(10) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C5 C4 C3 120.2(10) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? N1 C5 C4 120.8(10) . . ? N1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? O1 C6 O1 0.0(11) 1 . ? O1 C6 O2 124.3(10) 1 . ? O1 C6 O2 124.3(10) . . ? O1 C6 N2 127.1(9) 1 . ? O1 C6 N2 127.1(9) . . ? O2 C6 N2 108.6(9) . . ? C8 C7 O2 108.0(8) . . ? C8 C7 H7A 110.1 . . ? O2 C7 H7A 110.1 . . ? C8 C7 H7B 110.1 . . ? O2 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? C7 C8 C9 114.8(10) . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.5 . . ? O3 C9 C8 104.8(7) . . ? O3 C9 H9A 110.8 . . ? C8 C9 H9A 110.8 . . ? O3 C9 H9B 110.8 . . ? C8 C9 H9B 110.8 . . ? H9A C9 H9B 108.9 . . ? O4 C10 O4 0.0(4) 1 . ? O4 C10 O3 124.2(9) 1 . ? O4 C10 O3 124.2(9) . . ? O4 C10 N3 123.8(9) 1 . ? O4 C10 N3 123.8(9) . . ? O3 C10 N3 112.0(9) . . ? N3 C11 C15 117.6(8) . . ? N3 C11 C12 123.5(8) . . ? C15 C11 C12 118.8(9) . . ? N4 C12 C11 122.7(8) . . ? N4 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? N4 C13 C14 121.8(10) . . ? N4 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C13 C14 C15 119.8(9) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C11 C15 C14 117.8(10) . . ? C11 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? O1 O1 C6 0(10) 1 . ? C6 O2 C7 117.5(8) . . ? C10 O3 C9 115.4(8) . . ? O4 O4 C10 0(10) 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 Zn N1 C1 -128.0(8) 3_565 . . . ? Br1 Zn N1 C1 115.1(8) . . . . ? Br2 Zn N1 C1 -20.0(8) . . . . ? N4 Zn N1 C5 46.0(9) 3_565 . . . ? Br1 Zn N1 C5 -70.8(8) . . . . ? Br2 Zn N1 C5 154.1(8) . . . . ? C5 N1 C1 C2 -0.6(16) . . . . ? Zn N1 C1 C2 173.5(8) . . . . ? N1 C1 C2 N2 -179.1(10) . . . . ? N1 C1 C2 C3 -1.9(16) . . . . ? C6 N2 C2 C1 174.0(10) . . . . ? C6 N2 C2 C3 -3.0(16) . . . . ? C1 C2 C3 C4 3.7(15) . . . . ? N2 C2 C3 C4 -179.3(10) . . . . ? C2 C3 C4 C5 -3.2(17) . . . . ? C1 N1 C5 C4 1.2(16) . . . . ? Zn N1 C5 C4 -172.9(9) . . . . ? C3 C4 C5 N1 0.7(18) . . . . ? C2 N2 C6 O1 1.4(18) . . . 1 ? C2 N2 C6 O1 1.4(18) . . . . ? C2 N2 C6 O2 -178.5(9) . . . . ? O2 C7 C8 C9 -54.8(12) . . . . ? C7 C8 C9 O3 -69.9(11) . . . . ? C11 N3 C10 O4 -1.8(17) . . . 1 ? C11 N3 C10 O4 -1.8(17) . . . . ? C11 N3 C10 O3 179.4(10) . . . . ? C10 N3 C11 C15 -179.6(10) . . . . ? C10 N3 C11 C12 -0.8(16) . . . . ? C13 N4 C12 C11 -0.4(14) . . . . ? Zn N4 C12 C11 -172.9(7) 3_465 . . . ? N3 C11 C12 N4 -178.0(10) . . . . ? C15 C11 C12 N4 0.8(15) . . . . ? C12 N4 C13 C14 -0.8(15) . . . . ? Zn N4 C13 C14 171.4(8) 3_465 . . . ? N4 C13 C14 C15 1.6(17) . . . . ? N3 C11 C15 C14 178.8(10) . . . . ? C12 C11 C15 C14 0.0(16) . . . . ? C13 C14 C15 C11 -1.1(17) . . . . ? O2 C6 O1 O1 0.0(4) . . . 1 ? N2 C6 O1 O1 0.0(6) . . . 1 ? O1 C6 O2 C7 1.6(15) 1 . . . ? O1 C6 O2 C7 1.6(15) . . . . ? N2 C6 O2 C7 -178.5(8) . . . . ? C8 C7 O2 C6 174.8(9) . . . . ? O4 C10 O3 C9 1.5(15) 1 . . . ? O4 C10 O3 C9 1.5(15) . . . . ? N3 C10 O3 C9 -179.7(8) . . . . ? C8 C9 O3 C10 178.4(8) . . . . ? O3 C10 O4 O4 0.0(8) . . . 1 ? N3 C10 O4 O4 0.0(4) . . . 1 ? 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 C5 H5 O1 0.93 2.26 3.148(13) 159.3 4_544 C13 H13 O4 0.93 2.42 3.068(12) 126.4 4_454 C12 H12 O4 0.93 2.16 2.794(11) 124.8 1 C3 H3A O1 0.93 2.27 2.860(13) 120.5 1 N3 H3 Br2 0.86 2.70 3.451(7) 146.5 1_565 N2 H2 Br1 0.86 2.76 3.563(8) 155.8 2_565 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.72 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.768 _refine_diff_density_min -0.679 _refine_diff_density_rms 0.108 ############ data_X6 _database_code_depnum_ccdc_archive 'CCDC 819736' #TrackingRef '- complexes.txt' _audit_update_record ; 2011-05-17 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Br2 N4 O4 Zn' _chemical_formula_weight 555.53 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.136(10) _cell_length_b 10.495(8) _cell_length_c 16.018(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.568(9) _cell_angle_gamma 90.00 _cell_volume 2017(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.829 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 5.207 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3938 _exptl_absorpt_correction_T_max 0.5738 _exptl_absorpt_process_details ? _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 'Bruker APEX II area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8241 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 28.42 _reflns_number_total 2454 _reflns_number_gt 1911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0434P)^2^+1.3601P] 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 2454 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br Br 0.33397(3) 1.18031(3) 0.742399(19) 0.05003(13) Uani 1 1 d . . . Zn Zn 0.5000 1.06047(4) 0.7500 0.03775(14) Uani 1 2 d S . . O1 O 0.1833(2) 1.0158(3) 0.50876(15) 0.0741(8) Uani 1 1 d . . . O2 O 0.13354(18) 0.9275(2) 0.38170(12) 0.0458(5) Uani 1 1 d . . . N1 N 0.4891(2) 0.9427(2) 0.64699(14) 0.0386(5) Uani 1 1 d . . . N2 N 0.2966(2) 0.8777(2) 0.45259(14) 0.0412(6) Uani 1 1 d . . . H2 H 0.2990 0.8302 0.4092 0.049 Uiso 1 1 calc R . . C1 C 0.3972(2) 0.9441(3) 0.58960(17) 0.0380(6) Uani 1 1 d . . . H1 H 0.3364 0.9924 0.5999 0.046 Uiso 1 1 calc R . . C2 C 0.3900(2) 0.8752(3) 0.51483(16) 0.0352(6) Uani 1 1 d . . . C3 C 0.4809(3) 0.8026(3) 0.5022(2) 0.0450(7) Uani 1 1 d . . . H3 H 0.4791 0.7556 0.4527 0.054 Uiso 1 1 calc R . . C4 C 0.5738(3) 0.7996(3) 0.5623(2) 0.0519(8) Uani 1 1 d . . . H4 H 0.6346 0.7493 0.5547 0.062 Uiso 1 1 calc R . . C5 C 0.5759(3) 0.8717(3) 0.63392(19) 0.0450(7) Uani 1 1 d . . . H5 H 0.6395 0.8710 0.6743 0.054 Uiso 1 1 calc R . . C6 C 0.2022(3) 0.9472(3) 0.45310(17) 0.0409(7) Uani 1 1 d . . . C7 C 0.0357(3) 1.0093(4) 0.36867(19) 0.0504(8) Uani 1 1 d . . . H7A H 0.0582 1.0979 0.3674 0.060 Uiso 1 1 calc R . . H7B H -0.0075 0.9983 0.4145 0.060 Uiso 1 1 calc R . . C8 C -0.0330(3) 0.9739(3) 0.28682(18) 0.0466(7) Uani 1 1 d . . . H8A H -0.0944 1.0334 0.2749 0.056 Uiso 1 1 calc R . . H8B H -0.0642 0.8897 0.2921 0.056 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 Br 0.0380(2) 0.0657(2) 0.0459(2) 0.00661(13) 0.00476(14) 0.01028(14) Zn 0.0320(3) 0.0521(3) 0.0272(2) 0.000 -0.00217(18) 0.000 O1 0.0521(16) 0.123(2) 0.0422(13) -0.0344(15) -0.0087(11) 0.0283(16) O2 0.0397(12) 0.0618(13) 0.0325(10) -0.0081(9) -0.0062(9) 0.0066(10) N1 0.0387(14) 0.0459(13) 0.0289(11) 0.0011(9) -0.0026(10) 0.0017(10) N2 0.0385(14) 0.0555(14) 0.0277(11) -0.0106(10) -0.0010(10) 0.0017(11) C1 0.0320(15) 0.0494(16) 0.0313(13) -0.0009(11) 0.0008(11) 0.0030(12) C2 0.0351(16) 0.0397(14) 0.0300(13) 0.0012(10) 0.0019(11) -0.0038(12) C3 0.0470(19) 0.0462(16) 0.0418(16) -0.0085(12) 0.0063(14) 0.0031(14) C4 0.047(2) 0.0515(18) 0.057(2) -0.0050(14) 0.0059(16) 0.0154(15) C5 0.0382(18) 0.0499(16) 0.0441(16) 0.0033(13) -0.0036(13) 0.0069(14) C6 0.0348(16) 0.0575(17) 0.0296(13) -0.0034(12) 0.0021(11) -0.0047(13) C7 0.0425(19) 0.070(2) 0.0381(16) -0.0060(14) 0.0043(13) 0.0100(16) C8 0.0355(17) 0.0667(19) 0.0359(15) 0.0051(13) -0.0007(12) 0.0026(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br Zn 2.3630(15) . ? Zn N1 2.050(3) 2_656 ? Zn N1 2.050(3) . ? Zn Br 2.3630(15) 2_656 ? O1 C6 1.194(4) . ? O2 C6 1.327(4) . ? O2 C7 1.455(4) . ? N1 C5 1.332(4) . ? N1 C1 1.336(4) . ? N2 C6 1.359(4) . ? N2 C2 1.394(4) . ? N2 H2 0.8600 . ? C1 C2 1.391(4) . ? C1 H1 0.9300 . ? C2 C3 1.380(4) . ? C3 C4 1.370(5) . ? C3 H3 0.9300 . ? C4 C5 1.371(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.492(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.521(6) 2 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 Zn N1 105.85(14) 2_656 . ? N1 Zn Br 108.35(8) 2_656 . ? N1 Zn Br 109.09(7) . . ? N1 Zn Br 109.09(7) 2_656 2_656 ? N1 Zn Br 108.35(8) . 2_656 ? Br Zn Br 115.68(6) . 2_656 ? C6 O2 C7 115.2(2) . . ? C5 N1 C1 119.8(2) . . ? C5 N1 Zn 120.4(2) . . ? C1 N1 Zn 119.7(2) . . ? C6 N2 C2 127.0(2) . . ? C6 N2 H2 116.5 . . ? C2 N2 H2 116.5 . . ? N1 C1 C2 121.7(3) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 N2 119.2(3) . . ? C3 C2 C1 117.7(3) . . ? N2 C2 C1 123.1(3) . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 119.1(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 121.5(3) . . ? N1 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? O1 C6 O2 124.9(3) . . ? O1 C6 N2 125.7(3) . . ? O2 C6 N2 109.4(2) . . ? O2 C7 C8 108.4(3) . . ? O2 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? O2 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? C7 C8 C8 113.1(3) . 2 ? C7 C8 H8A 109.0 . . ? C8 C8 H8A 109.0 2 . ? C7 C8 H8B 109.0 . . ? C8 C8 H8B 109.0 2 . ? H8A C8 H8B 107.8 . . ? 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 Zn N1 C5 -68.3(2) 2_656 . . . ? Br Zn N1 C5 175.3(2) . . . . ? Br Zn N1 C5 48.6(2) 2_656 . . . ? N1 Zn N1 C1 116.5(2) 2_656 . . . ? Br Zn N1 C1 0.1(2) . . . . ? Br Zn N1 C1 -126.6(2) 2_656 . . . ? C5 N1 C1 C2 -1.5(4) . . . . ? Zn N1 C1 C2 173.8(2) . . . . ? C6 N2 C2 C3 -177.3(3) . . . . ? C6 N2 C2 C1 1.8(5) . . . . ? N1 C1 C2 C3 1.2(4) . . . . ? N1 C1 C2 N2 -178.0(3) . . . . ? N2 C2 C3 C4 179.5(3) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C2 C3 C4 C5 -1.5(5) . . . . ? C1 N1 C5 C4 0.3(5) . . . . ? Zn N1 C5 C4 -174.9(3) . . . . ? C3 C4 C5 N1 1.2(5) . . . . ? C7 O2 C6 O1 8.0(5) . . . . ? C7 O2 C6 N2 -171.9(3) . . . . ? C2 N2 C6 O1 -1.8(5) . . . . ? C2 N2 C6 O2 178.1(3) . . . . ? C6 O2 C7 C8 -179.2(3) . . . . ? O2 C7 C8 C8 -53.0(3) . . . 2 ? 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 N2 H2 Br 0.86 2.77 3.517(3) 146.3 6_575 C1 H1 O1 0.93 2.20 2.824(4) 123.8 . C4 H4 O1 0.93 2.65 3.423(5) 140.8 3_545 C7 H7B O1 0.97 2.62 3.541(5) 158.5 5_576 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 28.42 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.693 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.074 #########END