data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Zhong-Lu You' _publ_contact_author_email youzhonglu@yahoo.com.cn _publ_author_name 'Zhong-Lu You' data_4 #(CCDC 827062) _database_code_depnum_ccdc_archive 'CCDC 827062' #TrackingRef '- 5cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cl4 N4 O4 Zn2' _chemical_formula_weight 833.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4830(15) _cell_length_b 9.990(2) _cell_length_c 12.155(2) _cell_angle_alpha 75.27(3) _cell_angle_beta 85.00(3) _cell_angle_gamma 73.82(3) _cell_volume 843.8(3) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2494 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.3 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 1.784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7168 _exptl_absorpt_correction_T_max 0.8012 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'SMART CCD 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 7303 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3744 _reflns_number_gt 3139 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. In order to prove the existence of one H atom on N1. The H1 atom was located from a difference Fourier map, and refined isotropically, with N---H distance restrained to 0.90(1) \%A. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.1182P] 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 3744 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0883 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.19898(4) 0.00299(3) 0.44465(2) 0.03097(11) Uani 1 1 d . . . Cl1 Cl 0.46140(12) -0.31595(10) 1.02192(7) 0.0643(2) Uani 1 1 d . . . Cl2 Cl -0.04795(13) 0.70314(9) 0.09506(7) 0.0643(2) Uani 1 1 d . . . O1 O 0.0600(2) -0.01289(19) 0.59917(14) 0.0356(4) Uani 1 1 d . . . O2 O 0.2547(2) 0.18406(19) 0.44774(15) 0.0372(4) Uani 1 1 d . . . N1 N 0.3811(3) -0.1980(2) 0.50052(18) 0.0321(5) Uani 1 1 d D . . N2 N 0.2979(3) 0.0347(2) 0.27664(18) 0.0359(5) Uani 1 1 d . . . C1 C 0.2805(3) -0.2173(3) 0.7035(2) 0.0327(5) Uani 1 1 d . . . C2 C 0.1527(3) -0.0821(3) 0.6960(2) 0.0320(5) Uani 1 1 d . . . C3 C 0.1277(4) -0.0212(3) 0.7886(2) 0.0398(6) Uani 1 1 d . . . H3 H 0.0466 0.0695 0.7833 0.048 Uiso 1 1 calc R . . C4 C 0.2210(4) -0.0928(3) 0.8885(2) 0.0448(7) Uani 1 1 d . . . H4 H 0.2025 -0.0509 0.9502 0.054 Uiso 1 1 calc R . . C5 C 0.3416(4) -0.2269(3) 0.8963(2) 0.0416(6) Uani 1 1 d . . . C6 C 0.3725(4) -0.2884(3) 0.8044(2) 0.0383(6) Uani 1 1 d . . . H6 H 0.4558 -0.3784 0.8103 0.046 Uiso 1 1 calc R . . C7 C 0.3096(4) -0.2844(3) 0.6038(2) 0.0382(6) Uani 1 1 d . . . H7A H 0.3968 -0.3786 0.6245 0.046 Uiso 1 1 calc R . . H7B H 0.1923 -0.2974 0.5865 0.046 Uiso 1 1 calc R . . C8 C 0.4317(4) -0.2803(3) 0.4113(2) 0.0429(7) Uani 1 1 d . . . H8A H 0.3205 -0.2989 0.3901 0.051 Uiso 1 1 calc R . . H8B H 0.5178 -0.3723 0.4430 0.051 Uiso 1 1 calc R . . C9 C 0.5198(4) -0.2046(3) 0.3050(2) 0.0443(7) Uani 1 1 d . . . H9A H 0.6101 -0.1641 0.3280 0.053 Uiso 1 1 calc R . . H9B H 0.5867 -0.2754 0.2638 0.053 Uiso 1 1 calc R . . C10 C 0.3844(4) -0.0862(3) 0.2251(2) 0.0436(7) Uani 1 1 d . . . H10A H 0.4496 -0.0527 0.1554 0.052 Uiso 1 1 calc R . . H10B H 0.2884 -0.1239 0.2056 0.052 Uiso 1 1 calc R . . C11 C 0.2572(4) 0.1610(3) 0.2123(2) 0.0372(6) Uani 1 1 d . . . H11 H 0.2782 0.1698 0.1346 0.045 Uiso 1 1 calc R . . C12 C 0.1808(3) 0.2922(3) 0.2504(2) 0.0351(6) Uani 1 1 d . . . C13 C 0.1921(3) 0.2970(3) 0.3655(2) 0.0340(6) Uani 1 1 d . . . C14 C 0.1347(4) 0.4338(3) 0.3893(2) 0.0411(6) Uani 1 1 d . . . H14 H 0.1473 0.4412 0.4628 0.049 Uiso 1 1 calc R . . C15 C 0.0613(4) 0.5560(3) 0.3083(2) 0.0440(7) Uani 1 1 d . . . H15 H 0.0218 0.6443 0.3274 0.053 Uiso 1 1 calc R . . C16 C 0.0464(4) 0.5472(3) 0.1979(2) 0.0418(6) Uani 1 1 d . . . C17 C 0.1091(4) 0.4182(3) 0.1691(2) 0.0423(7) Uani 1 1 d . . . H17 H 0.1037 0.4146 0.0937 0.051 Uiso 1 1 calc R . . H1 H 0.487(3) -0.187(4) 0.521(3) 0.080 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02820(16) 0.03429(18) 0.02918(17) -0.00683(12) -0.00032(11) -0.00713(12) Cl1 0.0723(6) 0.0717(6) 0.0357(4) -0.0019(4) -0.0196(4) -0.0023(4) Cl2 0.0897(6) 0.0441(4) 0.0475(5) -0.0045(4) -0.0186(4) 0.0004(4) O1 0.0285(9) 0.0458(11) 0.0294(9) -0.0037(8) -0.0045(7) -0.0084(8) O2 0.0439(10) 0.0401(10) 0.0310(10) -0.0058(8) -0.0064(8) -0.0172(8) N1 0.0321(11) 0.0339(11) 0.0311(11) -0.0098(9) -0.0025(9) -0.0077(9) N2 0.0361(12) 0.0403(13) 0.0328(12) -0.0131(10) 0.0044(9) -0.0102(10) C1 0.0350(13) 0.0353(14) 0.0306(13) -0.0061(11) -0.0004(11) -0.0157(11) C2 0.0280(12) 0.0387(14) 0.0286(13) -0.0032(11) -0.0001(10) -0.0123(11) C3 0.0410(15) 0.0399(15) 0.0354(15) -0.0088(12) -0.0021(12) -0.0056(12) C4 0.0524(17) 0.0542(18) 0.0305(15) -0.0119(13) -0.0028(13) -0.0162(14) C5 0.0434(15) 0.0488(17) 0.0289(14) -0.0006(12) -0.0103(12) -0.0113(13) C6 0.0395(14) 0.0362(15) 0.0354(15) -0.0022(12) -0.0037(12) -0.0087(12) C7 0.0435(15) 0.0334(14) 0.0384(15) -0.0073(12) -0.0017(12) -0.0124(12) C8 0.0509(17) 0.0401(16) 0.0403(16) -0.0174(13) 0.0000(13) -0.0096(13) C9 0.0414(15) 0.0480(17) 0.0434(17) -0.0208(14) 0.0053(13) -0.0046(13) C10 0.0505(17) 0.0451(17) 0.0353(15) -0.0164(13) 0.0063(13) -0.0090(13) C11 0.0379(14) 0.0459(16) 0.0280(13) -0.0097(12) 0.0013(11) -0.0115(12) C12 0.0327(13) 0.0418(15) 0.0313(14) -0.0100(12) -0.0018(11) -0.0092(11) C13 0.0284(12) 0.0422(15) 0.0326(14) -0.0076(12) -0.0011(10) -0.0124(11) C14 0.0463(16) 0.0478(17) 0.0334(15) -0.0137(13) -0.0028(12) -0.0153(13) C15 0.0502(17) 0.0383(15) 0.0446(17) -0.0140(13) -0.0021(13) -0.0096(13) C16 0.0465(16) 0.0374(15) 0.0378(15) -0.0053(12) -0.0044(12) -0.0075(12) C17 0.0475(16) 0.0473(17) 0.0309(14) -0.0080(13) -0.0040(12) -0.0109(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.9761(18) . ? Zn1 O1 2.0241(17) 2_556 ? Zn1 O1 2.0576(18) . ? Zn1 N1 2.072(2) . ? Zn1 N2 2.087(2) . ? Cl1 C5 1.740(3) . ? Cl2 C16 1.743(3) . ? O1 C2 1.344(3) . ? O1 Zn1 2.0241(17) 2_556 ? O2 C13 1.306(3) . ? N1 C7 1.483(3) . ? N1 C8 1.485(3) . ? N1 H1 0.897(10) . ? N2 C11 1.274(3) . ? N2 C10 1.466(3) . ? C1 C6 1.383(4) . ? C1 C2 1.407(4) . ? C1 C7 1.500(4) . ? C2 C3 1.385(4) . ? C3 C4 1.379(4) . ? C3 H3 0.9300 . ? C4 C5 1.376(4) . ? C4 H4 0.9300 . ? C5 C6 1.380(4) . ? C6 H6 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.520(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.513(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.451(4) . ? C11 H11 0.9300 . ? C12 C17 1.390(4) . ? C12 C13 1.422(3) . ? C13 C14 1.410(4) . ? C14 C15 1.367(4) . ? C14 H14 0.9300 . ? C15 C16 1.383(4) . ? C15 H15 0.9300 . ? C16 C17 1.367(4) . ? C17 H17 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 O2 Zn1 O1 118.11(8) . 2_556 ? O2 Zn1 O1 93.74(8) . . ? O1 Zn1 O1 78.14(8) 2_556 . ? O2 Zn1 N1 123.54(8) . . ? O1 Zn1 N1 118.00(8) 2_556 . ? O1 Zn1 N1 91.69(8) . . ? O2 Zn1 N2 87.13(8) . . ? O1 Zn1 N2 93.40(8) 2_556 . ? O1 Zn1 N2 170.84(7) . . ? N1 Zn1 N2 95.43(9) . . ? C2 O1 Zn1 130.16(15) . 2_556 ? C2 O1 Zn1 120.40(15) . . ? Zn1 O1 Zn1 101.86(8) 2_556 . ? C13 O2 Zn1 118.11(15) . . ? C7 N1 C8 110.0(2) . . ? C7 N1 Zn1 112.11(16) . . ? C8 N1 Zn1 113.22(16) . . ? C7 N1 H1 105(2) . . ? C8 N1 H1 107(2) . . ? Zn1 N1 H1 109(2) . . ? C11 N2 C10 118.4(2) . . ? C11 N2 Zn1 119.01(18) . . ? C10 N2 Zn1 121.67(17) . . ? C6 C1 C2 119.3(2) . . ? C6 C1 C7 121.1(2) . . ? C2 C1 C7 119.6(2) . . ? O1 C2 C3 121.1(2) . . ? O1 C2 C1 119.9(2) . . ? C3 C2 C1 119.0(2) . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 Cl1 119.3(2) . . ? C6 C5 Cl1 120.1(2) . . ? C5 C6 C1 120.5(2) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N1 C7 C1 113.3(2) . . ? N1 C7 H7A 108.9 . . ? C1 C7 H7A 108.9 . . ? N1 C7 H7B 108.9 . . ? C1 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? N1 C8 C9 113.9(2) . . ? N1 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? N1 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 114.9(2) . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? N2 C10 C9 111.4(2) . . ? N2 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? N2 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? N2 C11 C12 125.3(2) . . ? N2 C11 H11 117.3 . . ? C12 C11 H11 117.3 . . ? C17 C12 C13 119.8(2) . . ? C17 C12 C11 118.1(2) . . ? C13 C12 C11 121.9(2) . . ? O2 C13 C14 119.3(2) . . ? O2 C13 C12 124.0(2) . . ? C14 C13 C12 116.7(2) . . ? C15 C14 C13 122.5(3) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C14 C15 C16 119.4(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 120.4(3) . . ? C17 C16 Cl2 120.3(2) . . ? C15 C16 Cl2 119.3(2) . . ? C16 C17 C12 121.1(3) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.897(10) 2.010(12) 2.898(3) 170(3) 2_656 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.397 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.066 data_5 #(CCDC 827063) _database_code_depnum_ccdc_archive 'CCDC 827063' #TrackingRef '- 5cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Br4 N4 O4 Zn2' _chemical_formula_weight 1011.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0080(14) _cell_length_b 10.081(2) _cell_length_c 13.095(3) _cell_angle_alpha 100.62(3) _cell_angle_beta 95.51(3) _cell_angle_gamma 104.03(3) _cell_volume 872.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1075 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 26.8 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.924 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 5.999 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3800 _exptl_absorpt_correction_T_max 0.4115 _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 'SMART CCD 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 7290 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.1001 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3819 _reflns_number_gt 2330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. In order to prove the existence of one H atom on N1. The H1 atom was located from a difference Fourier map, and refined isotropically, with N---H distance restrained to 0.90(1) \%A. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+1.0028P] 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 3819 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.1360 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.28276(12) 0.96857(9) 0.43437(7) 0.0297(3) Uani 1 1 d . . . Br1 Br 0.20067(16) 0.75988(14) 0.95432(8) 0.0751(4) Uani 1 1 d . . . Br2 Br 0.37908(17) 1.49885(12) 0.11368(8) 0.0693(4) Uani 1 1 d . . . O1 O 0.4366(7) 1.0270(5) 0.5925(4) 0.0329(12) Uani 1 1 d . . . O2 O 0.2405(7) 1.1574(5) 0.4451(4) 0.0362(13) Uani 1 1 d . . . N1 N 0.1116(9) 0.7888(7) 0.4688(5) 0.0335(15) Uani 1 1 d D . . N2 N 0.1327(9) 0.9195(7) 0.2769(5) 0.0366(16) Uani 1 1 d . . . C1 C 0.2702(10) 0.8283(8) 0.6556(6) 0.0318(18) Uani 1 1 d . . . C2 C 0.3718(11) 0.9705(9) 0.6740(6) 0.0352(19) Uani 1 1 d . . . C3 C 0.4089(11) 1.0505(9) 0.7759(6) 0.0365(19) Uani 1 1 d . . . H3 H 0.4680 1.1462 0.7881 0.044 Uiso 1 1 calc R . . C4 C 0.3580(12) 0.9885(10) 0.8606(7) 0.046(2) Uani 1 1 d . . . H4 H 0.3864 1.0421 0.9288 0.055 Uiso 1 1 calc R . . C5 C 0.2659(12) 0.8478(10) 0.8416(6) 0.043(2) Uani 1 1 d . . . C6 C 0.2185(11) 0.7710(9) 0.7410(6) 0.042(2) Uani 1 1 d . . . H6 H 0.1491 0.6771 0.7291 0.050 Uiso 1 1 calc R . . C7 C 0.2292(12) 0.7393(9) 0.5465(6) 0.043(2) Uani 1 1 d . . . H7A H 0.3550 0.7357 0.5227 0.052 Uiso 1 1 calc R . . H7B H 0.1585 0.6447 0.5489 0.052 Uiso 1 1 calc R . . C8 C 0.0113(13) 0.6684(9) 0.3805(6) 0.046(2) Uani 1 1 d . . . H8A H -0.0785 0.5991 0.4083 0.056 Uiso 1 1 calc R . . H8B H 0.1115 0.6260 0.3534 0.056 Uiso 1 1 calc R . . C9 C -0.1035(12) 0.7017(10) 0.2913(7) 0.051(2) Uani 1 1 d . . . H9A H -0.1878 0.7587 0.3192 0.061 Uiso 1 1 calc R . . H9B H -0.1894 0.6151 0.2482 0.061 Uiso 1 1 calc R . . C10 C 0.0259(14) 0.7786(9) 0.2222(7) 0.050(2) Uani 1 1 d . . . H10A H 0.1205 0.7270 0.2001 0.060 Uiso 1 1 calc R . . H10B H -0.0572 0.7825 0.1597 0.060 Uiso 1 1 calc R . . C11 C 0.1455(11) 1.0154(9) 0.2236(6) 0.039(2) Uani 1 1 d . . . H11 H 0.0922 0.9863 0.1528 0.047 Uiso 1 1 calc R . . C12 C 0.2339(10) 1.1633(8) 0.2620(6) 0.0323(18) Uani 1 1 d . . . C13 C 0.2695(10) 1.2281(9) 0.3714(6) 0.0349(19) Uani 1 1 d . . . C14 C 0.3364(12) 1.3734(9) 0.3975(7) 0.043(2) Uani 1 1 d . . . H14 H 0.3588 1.4183 0.4680 0.051 Uiso 1 1 calc R . . C15 C 0.3713(12) 1.4546(9) 0.3221(7) 0.045(2) Uani 1 1 d . . . H15 H 0.4156 1.5517 0.3420 0.054 Uiso 1 1 calc R . . C16 C 0.3390(12) 1.3886(9) 0.2179(7) 0.041(2) Uani 1 1 d . . . C17 C 0.2690(12) 1.2458(10) 0.1863(7) 0.043(2) Uani 1 1 d . . . H17 H 0.2448 1.2037 0.1152 0.052 Uiso 1 1 calc R . . H1 H 0.010(9) 0.813(10) 0.498(7) 0.080 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0264(5) 0.0356(5) 0.0293(5) 0.0123(4) 0.0063(4) 0.0072(4) Br1 0.0653(7) 0.1151(10) 0.0435(6) 0.0463(6) 0.0087(5) -0.0006(6) Br2 0.0837(8) 0.0722(8) 0.0632(7) 0.0447(6) 0.0213(6) 0.0150(6) O1 0.027(3) 0.045(3) 0.033(3) 0.021(3) 0.011(2) 0.009(2) O2 0.043(3) 0.047(3) 0.030(3) 0.019(3) 0.015(2) 0.021(3) N1 0.036(4) 0.035(4) 0.029(4) 0.011(3) -0.001(3) 0.006(3) N2 0.029(4) 0.042(4) 0.039(4) 0.014(3) 0.003(3) 0.007(3) C1 0.029(4) 0.039(5) 0.030(4) 0.016(4) 0.004(3) 0.007(4) C2 0.028(4) 0.054(6) 0.031(5) 0.015(4) 0.010(3) 0.020(4) C3 0.029(4) 0.044(5) 0.037(5) 0.008(4) 0.002(4) 0.011(4) C4 0.036(5) 0.077(7) 0.031(5) 0.016(5) 0.007(4) 0.020(5) C5 0.033(5) 0.065(6) 0.036(5) 0.025(5) 0.012(4) 0.008(4) C6 0.031(5) 0.052(6) 0.044(5) 0.021(5) 0.003(4) 0.006(4) C7 0.045(5) 0.043(5) 0.043(5) 0.019(4) 0.005(4) 0.007(4) C8 0.048(5) 0.046(6) 0.041(5) 0.005(4) 0.005(4) 0.009(4) C9 0.043(5) 0.053(6) 0.047(6) 0.009(5) -0.008(4) 0.003(4) C10 0.063(6) 0.042(5) 0.038(5) 0.009(4) -0.003(4) 0.003(5) C11 0.030(4) 0.058(6) 0.031(5) 0.013(4) 0.006(3) 0.013(4) C12 0.029(4) 0.045(5) 0.029(4) 0.017(4) 0.007(3) 0.013(4) C13 0.027(4) 0.050(5) 0.039(5) 0.023(4) 0.014(4) 0.018(4) C14 0.042(5) 0.042(5) 0.045(5) 0.011(4) 0.007(4) 0.010(4) C15 0.043(5) 0.042(5) 0.060(6) 0.024(5) 0.015(4) 0.016(4) C16 0.042(5) 0.053(6) 0.041(5) 0.030(4) 0.017(4) 0.019(4) C17 0.043(5) 0.062(6) 0.036(5) 0.018(4) 0.011(4) 0.028(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.978(5) . ? Zn1 O1 2.022(5) 2_676 ? Zn1 N1 2.068(6) . ? Zn1 N2 2.135(6) . ? Zn1 O1 2.147(5) . ? Br1 C5 1.895(8) . ? Br2 C16 1.912(7) . ? O1 C2 1.365(8) . ? O1 Zn1 2.022(5) 2_676 ? O2 C13 1.304(8) . ? N1 C7 1.479(9) . ? N1 C8 1.489(10) . ? N1 H1 0.901(10) . ? N2 C11 1.284(9) . ? N2 C10 1.448(10) . ? C1 C6 1.389(10) . ? C1 C2 1.401(11) . ? C1 C7 1.500(11) . ? C2 C3 1.391(10) . ? C3 C4 1.404(11) . ? C3 H3 0.9300 . ? C4 C5 1.373(12) . ? C4 H4 0.9300 . ? C5 C6 1.364(11) . ? C6 H6 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.489(11) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.523(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.441(11) . ? C11 H11 0.9300 . ? C12 C17 1.409(10) . ? C12 C13 1.432(11) . ? C13 C14 1.391(11) . ? C14 C15 1.398(11) . ? C14 H14 0.9300 . ? C15 C16 1.374(12) . ? C15 H15 0.9300 . ? C16 C17 1.372(12) . ? C17 H17 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 O2 Zn1 O1 110.0(2) . 2_676 ? O2 Zn1 N1 131.1(2) . . ? O1 Zn1 N1 118.1(2) 2_676 . ? O2 Zn1 N2 87.0(2) . . ? O1 Zn1 N2 100.4(2) 2_676 . ? N1 Zn1 N2 92.8(2) . . ? O2 Zn1 O1 90.8(2) . . ? O1 Zn1 O1 79.5(2) 2_676 . ? N1 Zn1 O1 89.3(2) . . ? N2 Zn1 O1 177.6(2) . . ? C2 O1 Zn1 117.6(4) . 2_676 ? C2 O1 Zn1 125.0(5) . . ? Zn1 O1 Zn1 100.5(2) 2_676 . ? C13 O2 Zn1 123.1(5) . . ? C7 N1 C8 108.8(6) . . ? C7 N1 Zn1 110.2(5) . . ? C8 N1 Zn1 118.5(5) . . ? C7 N1 H1 109(6) . . ? C8 N1 H1 104(6) . . ? Zn1 N1 H1 106(6) . . ? C11 N2 C10 116.6(7) . . ? C11 N2 Zn1 120.1(6) . . ? C10 N2 Zn1 123.1(5) . . ? C6 C1 C2 118.5(8) . . ? C6 C1 C7 121.2(7) . . ? C2 C1 C7 120.2(7) . . ? O1 C2 C3 121.2(7) . . ? O1 C2 C1 119.7(7) . . ? C3 C2 C1 119.1(7) . . ? C2 C3 C4 120.8(8) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.3(8) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 120.0(8) . . ? C6 C5 Br1 119.7(7) . . ? C4 C5 Br1 120.3(7) . . ? C5 C6 C1 122.3(8) . . ? C5 C6 H6 118.9 . . ? C1 C6 H6 118.9 . . ? N1 C7 C1 114.5(7) . . ? N1 C7 H7A 108.6 . . ? C1 C7 H7A 108.6 . . ? N1 C7 H7B 108.6 . . ? C1 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N1 C8 C9 116.0(7) . . ? N1 C8 H8A 108.3 . . ? C9 C8 H8A 108.3 . . ? N1 C8 H8B 108.3 . . ? C9 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C8 C9 C10 113.9(7) . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? N2 C10 C9 111.7(7) . . ? N2 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? N2 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? N2 C11 C12 126.8(7) . . ? N2 C11 H11 116.6 . . ? C12 C11 H11 116.6 . . ? C17 C12 C13 120.2(8) . . ? C17 C12 C11 117.0(7) . . ? C13 C12 C11 122.5(7) . . ? O2 C13 C14 120.1(8) . . ? O2 C13 C12 123.1(7) . . ? C14 C13 C12 116.8(7) . . ? C13 C14 C15 122.7(8) . . ? C13 C14 H14 118.7 . . ? C15 C14 H14 118.7 . . ? C16 C15 C14 118.9(8) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C17 C16 C15 121.6(7) . . ? C17 C16 Br2 119.0(7) . . ? C15 C16 Br2 119.2(7) . . ? C16 C17 C12 119.8(8) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? 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 N1 H1 O2 0.901(10) 2.039(18) 2.935(8) 173(9) 2_576 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.888 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.131 data_1 #(CCDC 827064) _database_code_depnum_ccdc_archive 'CCDC 827064' #TrackingRef '- 5cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H34 Cl4 N4 Ni3 O8' _chemical_formula_weight 992.62 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3468(12) _cell_length_b 11.5073(15) _cell_length_c 18.539(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.774(2) _cell_angle_gamma 90.00 _cell_volume 1989.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4173 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 1.731 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6074 _exptl_absorpt_correction_T_max 0.6522 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'SMART CCD 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 11532 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4551 _reflns_number_gt 3428 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+1.1704P] 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 4551 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Ni1 Ni 0.84322(4) 0.86105(3) 0.107538(18) 0.04150(12) Uani 1 1 d . . . Ni2 Ni 1.0000 1.0000 0.0000 0.03896(14) Uani 1 2 d S . . Cl1 Cl 0.86492(14) 1.41558(9) 0.29490(5) 0.0841(3) Uani 1 1 d . . . Cl2 Cl 1.41679(12) 0.45400(8) 0.07984(6) 0.0821(3) Uani 1 1 d . . . O1 O 0.8945(2) 1.02734(16) 0.09296(10) 0.0452(5) Uani 1 1 d . . . O2 O 1.0042(2) 0.83650(16) 0.04298(10) 0.0434(5) Uani 1 1 d . . . O3 O 0.6862(2) 0.85186(18) 0.03020(10) 0.0500(5) Uani 1 1 d . . . O4 O 0.8039(2) 0.95457(18) -0.04971(10) 0.0484(5) Uani 1 1 d . . . N1 N 0.7120(3) 0.9075(2) 0.18566(13) 0.0523(6) Uani 1 1 d . . . N2 N 0.8427(3) 0.6872(2) 0.13370(14) 0.0523(6) Uani 1 1 d . . . C1 C 0.8006(3) 1.1068(3) 0.19869(15) 0.0439(6) Uani 1 1 d . . . C2 C 0.8905(3) 1.1121(2) 0.13981(14) 0.0416(6) Uani 1 1 d . . . C3 C 0.9731(4) 1.2125(3) 0.13324(16) 0.0540(8) Uani 1 1 d . . . H3 H 1.0341 1.2177 0.0957 0.065 Uiso 1 1 calc R . . C4 C 0.9664(4) 1.3036(3) 0.18065(17) 0.0597(8) Uani 1 1 d . . . H4 H 1.0238 1.3687 0.1754 0.072 Uiso 1 1 calc R . . C5 C 0.8752(4) 1.2991(3) 0.23591(16) 0.0556(8) Uani 1 1 d . . . C6 C 0.7941(3) 1.2014(3) 0.24550(16) 0.0522(7) Uani 1 1 d . . . H6 H 0.7343 1.1982 0.2836 0.063 Uiso 1 1 calc R . . C7 C 0.7094(3) 1.0081(3) 0.21304(17) 0.0534(8) Uani 1 1 d . . . H7 H 0.6408 1.0205 0.2464 0.064 Uiso 1 1 calc R . . C8 C 0.5989(4) 0.8266(3) 0.20494(19) 0.0642(9) Uani 1 1 d . . . H8A H 0.5254 0.8233 0.1655 0.077 Uiso 1 1 calc R . . H8B H 0.5549 0.8558 0.2473 0.077 Uiso 1 1 calc R . . C9 C 0.6549(4) 0.7057(3) 0.22040(19) 0.0654(10) Uani 1 1 d . . . H9A H 0.7342 0.7107 0.2567 0.079 Uiso 1 1 calc R . . H9B H 0.5798 0.6605 0.2408 0.079 Uiso 1 1 calc R . . C10 C 0.7050(4) 0.6415(3) 0.1559(2) 0.0612(9) Uani 1 1 d . . . H10A H 0.7157 0.5597 0.1676 0.073 Uiso 1 1 calc R . . H10B H 0.6332 0.6485 0.1159 0.073 Uiso 1 1 calc R . . C11 C 0.9019(5) 0.6175(3) 0.0827(3) 0.0889(15) Uani 1 1 d . . . H11 H 0.8489 0.5600 0.0579 0.107 Uiso 1 1 calc R . . C12 C 1.0546(4) 0.6394(3) 0.06970(18) 0.0539(8) Uani 1 1 d . . . C13 C 1.0989(3) 0.7511(2) 0.04940(14) 0.0429(6) Uani 1 1 d . . . C14 C 1.2425(3) 0.7660(3) 0.03555(16) 0.0501(7) Uani 1 1 d . . . H14 H 1.2736 0.8385 0.0208 0.060 Uiso 1 1 calc R . . C15 C 1.3397(4) 0.6760(3) 0.04317(18) 0.0561(8) Uani 1 1 d . . . H15 H 1.4349 0.6878 0.0332 0.067 Uiso 1 1 calc R . . C16 C 1.2951(4) 0.5687(3) 0.06566(17) 0.0569(8) Uani 1 1 d . . . C17 C 1.1558(4) 0.5501(3) 0.07756(19) 0.0607(9) Uani 1 1 d . . . H17 H 1.1267 0.4765 0.0912 0.073 Uiso 1 1 calc R . . C18 C 0.5674(4) 0.8936(4) -0.08300(19) 0.0713(10) Uani 1 1 d . . . H18A H 0.5929 0.9183 -0.1299 0.107 Uiso 1 1 calc R . . H18B H 0.4933 0.9431 -0.0669 0.107 Uiso 1 1 calc R . . H18C H 0.5334 0.8149 -0.0857 0.107 Uiso 1 1 calc R . . C19 C 0.6973(3) 0.9005(3) -0.03032(15) 0.0454(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0521(2) 0.0387(2) 0.03497(19) 0.00650(14) 0.01235(15) -0.00382(16) Ni2 0.0512(3) 0.0342(3) 0.0328(2) 0.00692(19) 0.0133(2) 0.0005(2) Cl1 0.1421(10) 0.0592(6) 0.0517(5) -0.0175(4) 0.0118(5) -0.0135(6) Cl2 0.0907(7) 0.0525(5) 0.1044(8) 0.0133(5) 0.0153(6) 0.0239(5) O1 0.0622(12) 0.0373(10) 0.0382(10) 0.0017(8) 0.0196(9) -0.0024(9) O2 0.0526(11) 0.0361(10) 0.0433(11) 0.0100(8) 0.0161(9) 0.0025(8) O3 0.0547(12) 0.0556(13) 0.0404(11) 0.0083(9) 0.0072(9) -0.0064(10) O4 0.0575(12) 0.0487(12) 0.0395(10) 0.0085(9) 0.0078(9) -0.0027(10) N1 0.0589(16) 0.0551(16) 0.0455(14) -0.0022(12) 0.0229(12) -0.0153(13) N2 0.0555(15) 0.0415(14) 0.0614(16) 0.0136(12) 0.0147(12) -0.0093(12) C1 0.0497(16) 0.0432(16) 0.0394(15) 0.0012(12) 0.0076(12) 0.0018(12) C2 0.0505(16) 0.0407(15) 0.0342(13) 0.0054(11) 0.0075(12) 0.0025(12) C3 0.074(2) 0.0477(18) 0.0425(16) 0.0013(13) 0.0171(14) -0.0078(15) C4 0.084(2) 0.0484(18) 0.0476(17) 0.0012(14) 0.0092(16) -0.0207(17) C5 0.079(2) 0.0483(18) 0.0397(16) -0.0047(13) 0.0034(14) 0.0002(16) C6 0.0626(19) 0.0551(19) 0.0398(15) -0.0015(13) 0.0094(13) 0.0028(15) C7 0.0504(17) 0.056(2) 0.0563(18) -0.0013(15) 0.0214(14) 0.0006(14) C8 0.062(2) 0.069(2) 0.064(2) -0.0029(17) 0.0269(17) -0.0205(18) C9 0.060(2) 0.076(3) 0.062(2) 0.0215(18) 0.0143(16) -0.0182(18) C10 0.0559(19) 0.0506(19) 0.078(2) 0.0162(17) 0.0091(17) -0.0107(15) C11 0.086(3) 0.042(2) 0.145(4) -0.022(2) 0.055(3) -0.0206(19) C12 0.065(2) 0.0365(16) 0.0617(19) 0.0029(14) 0.0171(16) -0.0018(14) C13 0.0574(17) 0.0367(15) 0.0358(14) 0.0018(11) 0.0114(12) -0.0012(13) C14 0.0589(18) 0.0368(15) 0.0559(18) 0.0064(13) 0.0131(14) 0.0008(13) C15 0.0557(19) 0.0496(18) 0.064(2) 0.0026(15) 0.0133(15) 0.0023(15) C16 0.071(2) 0.0430(17) 0.0576(19) 0.0041(14) 0.0119(16) 0.0137(16) C17 0.083(2) 0.0334(16) 0.068(2) 0.0051(14) 0.0223(18) -0.0020(16) C18 0.068(2) 0.091(3) 0.054(2) 0.0109(19) -0.0031(17) -0.010(2) C19 0.0553(17) 0.0410(16) 0.0406(15) -0.0020(12) 0.0073(13) 0.0021(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O3 1.986(2) . ? Ni1 O1 1.9954(19) . ? Ni1 O2 2.0032(18) . ? Ni1 N1 2.030(2) . ? Ni1 N2 2.059(2) . ? Ni2 O2 2.0426(18) 3_775 ? Ni2 O2 2.0426(18) . ? Ni2 O4 2.064(2) 3_775 ? Ni2 O4 2.064(2) . ? Ni2 O1 2.0652(18) 3_775 ? Ni2 O1 2.0652(18) . ? Cl1 C5 1.736(3) . ? Cl2 C16 1.750(3) . ? O1 C2 1.308(3) . ? O2 C13 1.323(3) . ? O3 C19 1.264(3) . ? O4 C19 1.248(3) . ? N1 C7 1.265(4) . ? N1 C8 1.471(4) . ? N2 C11 1.383(5) . ? N2 C10 1.474(4) . ? C1 C6 1.396(4) . ? C1 C2 1.422(4) . ? C1 C7 1.455(4) . ? C2 C3 1.400(4) . ? C3 C4 1.372(4) . ? C3 H3 0.9300 . ? C4 C5 1.377(5) . ? C4 H4 0.9300 . ? C5 C6 1.374(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.507(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.507(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.484(5) . ? C11 H11 0.9300 . ? C12 C17 1.398(5) . ? C12 C13 1.409(4) . ? C13 C14 1.394(4) . ? C14 C15 1.379(4) . ? C14 H14 0.9300 . ? C15 C16 1.377(5) . ? C15 H15 0.9300 . ? C16 C17 1.352(5) . ? C17 H17 0.9300 . ? C18 C19 1.509(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 O3 Ni1 O1 97.24(8) . . ? O3 Ni1 O2 96.30(8) . . ? O1 Ni1 O2 81.82(8) . . ? O3 Ni1 N1 94.39(10) . . ? O1 Ni1 N1 90.32(9) . . ? O2 Ni1 N1 167.44(10) . . ? O3 Ni1 N2 96.04(10) . . ? O1 Ni1 N2 165.51(10) . . ? O2 Ni1 N2 90.99(9) . . ? N1 Ni1 N2 94.42(10) . . ? O2 Ni2 O2 180.00(10) 3_775 . ? O2 Ni2 O4 86.25(8) 3_775 3_775 ? O2 Ni2 O4 93.75(8) . 3_775 ? O2 Ni2 O4 93.75(8) 3_775 . ? O2 Ni2 O4 86.25(8) . . ? O4 Ni2 O4 180.0 3_775 . ? O2 Ni2 O1 79.21(7) 3_775 3_775 ? O2 Ni2 O1 100.79(7) . 3_775 ? O4 Ni2 O1 87.28(8) 3_775 3_775 ? O4 Ni2 O1 92.72(8) . 3_775 ? O2 Ni2 O1 100.79(7) 3_775 . ? O2 Ni2 O1 79.21(7) . . ? O4 Ni2 O1 92.72(8) 3_775 . ? O4 Ni2 O1 87.28(8) . . ? O1 Ni2 O1 180.0 3_775 . ? C2 O1 Ni1 127.40(16) . . ? C2 O1 Ni2 134.73(17) . . ? Ni1 O1 Ni2 95.69(8) . . ? C13 O2 Ni1 125.12(16) . . ? C13 O2 Ni2 135.66(17) . . ? Ni1 O2 Ni2 96.16(8) . . ? C19 O3 Ni1 121.1(2) . . ? C19 O4 Ni2 134.47(19) . . ? C7 N1 C8 116.7(3) . . ? C7 N1 Ni1 123.8(2) . . ? C8 N1 Ni1 119.0(2) . . ? C11 N2 C10 112.3(3) . . ? C11 N2 Ni1 113.3(2) . . ? C10 N2 Ni1 115.4(2) . . ? C6 C1 C2 119.7(3) . . ? C6 C1 C7 116.4(3) . . ? C2 C1 C7 123.8(3) . . ? O1 C2 C3 121.2(3) . . ? O1 C2 C1 121.5(3) . . ? C3 C2 C1 117.3(3) . . ? C4 C3 C2 121.8(3) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 120.3(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.1(3) . . ? C6 C5 Cl1 119.8(3) . . ? C4 C5 Cl1 120.1(3) . . ? C5 C6 C1 120.7(3) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? N1 C7 C1 127.9(3) . . ? N1 C7 H7 116.1 . . ? C1 C7 H7 116.1 . . ? N1 C8 C9 112.6(3) . . ? N1 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 115.1(3) . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? N2 C10 C9 111.7(3) . . ? N2 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? N2 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? N2 C11 C12 116.4(3) . . ? N2 C11 H11 121.8 . . ? C12 C11 H11 121.8 . . ? C17 C12 C13 119.3(3) . . ? C17 C12 C11 120.6(3) . . ? C13 C12 C11 120.1(3) . . ? O2 C13 C14 122.6(2) . . ? O2 C13 C12 119.7(3) . . ? C14 C13 C12 117.7(3) . . ? C15 C14 C13 121.7(3) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C16 C15 C14 119.6(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C17 C16 C15 120.4(3) . . ? C17 C16 Cl2 118.6(3) . . ? C15 C16 Cl2 121.0(3) . . ? C16 C17 C12 121.3(3) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C19 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 C19 O3 126.2(3) . . ? O4 C19 C18 117.6(3) . . ? O3 C19 C18 116.2(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.453 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.061 data_2 #(CCDC 827065) _database_code_depnum_ccdc_archive 'CCDC 827065' #TrackingRef '- 5cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H34 Br4 N4 Ni3 O8' _chemical_formula_weight 1170.46 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.111(4) _cell_length_b 12.089(6) _cell_length_c 18.724(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.117(7) _cell_angle_gamma 90.00 _cell_volume 2060.9(16) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1622 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.1 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.886 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1156 _exptl_absorpt_coefficient_mu 5.290 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3759 _exptl_absorpt_correction_T_max 0.4176 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'SMART CCD 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 10573 _diffrn_reflns_av_R_equivalents 0.0542 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.55 _reflns_number_total 3844 _reflns_number_gt 2063 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+4.5369P] 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 3844 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1213 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1613 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 Ni1 Ni 0.17055(12) 0.62056(8) 0.38961(5) 0.0572(3) Uani 1 1 d . . . Ni2 Ni 0.0000 0.5000 0.5000 0.0529(4) Uani 1 2 d S . . Br1 Br -0.40815(18) 1.04015(10) 0.41676(7) 0.1311(6) Uani 1 1 d . . . Br2 Br 0.12006(13) 0.07335(8) 0.21237(5) 0.0894(4) Uani 1 1 d . . . O1 O 0.0035(6) 0.6526(4) 0.4516(2) 0.0568(14) Uani 1 1 d . . . O2 O 0.1103(6) 0.4648(4) 0.4089(2) 0.0558(14) Uani 1 1 d . . . O3 O 0.3261(6) 0.6321(4) 0.4670(3) 0.0620(14) Uani 1 1 d . . . O4 O 0.1988(7) 0.5412(4) 0.5481(3) 0.0618(15) Uani 1 1 d . . . N1 N 0.1800(9) 0.7835(6) 0.3600(4) 0.072(2) Uani 1 1 d . . . N2 N 0.3033(7) 0.5659(6) 0.3137(3) 0.0625(18) Uani 1 1 d . . . C1 C -0.0364(14) 0.8399(7) 0.4212(6) 0.093(3) Uani 1 1 d . . . C2 C -0.0896(11) 0.7360(7) 0.4454(4) 0.062(2) Uani 1 1 d . . . C3 C -0.2355(11) 0.7292(7) 0.4637(4) 0.069(2) Uani 1 1 d . . . H3 H -0.2717 0.6625 0.4805 0.083 Uiso 1 1 calc R . . C4 C -0.3278(12) 0.8194(7) 0.4575(4) 0.078(3) Uani 1 1 d . . . H4 H -0.4242 0.8130 0.4716 0.094 Uiso 1 1 calc R . . C5 C -0.2807(14) 0.9179(8) 0.4310(5) 0.088(3) Uani 1 1 d . . . C6 C -0.1377(16) 0.9275(8) 0.4149(6) 0.113(4) Uani 1 1 d . . . H6 H -0.1047 0.9956 0.3989 0.136 Uiso 1 1 calc R . . C7 C 0.1144(16) 0.8530(9) 0.4004(10) 0.169(8) Uani 1 1 d . . . H7 H 0.1666 0.9145 0.4171 0.203 Uiso 1 1 calc R . . C8 C 0.3193(12) 0.8228(8) 0.3313(6) 0.092(3) Uani 1 1 d . . . H8A H 0.3950 0.8222 0.3690 0.111 Uiso 1 1 calc R . . H8B H 0.3072 0.8984 0.3148 0.111 Uiso 1 1 calc R . . C9 C 0.3672(11) 0.7511(9) 0.2700(5) 0.086(3) Uani 1 1 d . . . H9A H 0.2845 0.7422 0.2364 0.103 Uiso 1 1 calc R . . H9B H 0.4437 0.7898 0.2454 0.103 Uiso 1 1 calc R . . C10 C 0.4232(10) 0.6387(8) 0.2906(5) 0.080(3) Uani 1 1 d . . . H10A H 0.4699 0.6054 0.2501 0.096 Uiso 1 1 calc R . . H10B H 0.4966 0.6458 0.3292 0.096 Uiso 1 1 calc R . . C11 C 0.2977(10) 0.4696(8) 0.2870(4) 0.068(2) Uani 1 1 d . . . H11 H 0.3636 0.4546 0.2515 0.081 Uiso 1 1 calc R . . C12 C 0.2013(9) 0.3815(7) 0.3053(4) 0.0540(19) Uani 1 1 d . . . C13 C 0.1104(9) 0.3805(6) 0.3641(4) 0.0496(18) Uani 1 1 d . . . C14 C 0.0217(10) 0.2882(6) 0.3751(4) 0.064(2) Uani 1 1 d . . . H14 H -0.0403 0.2872 0.4134 0.076 Uiso 1 1 calc R . . C15 C 0.0252(10) 0.2000(7) 0.3304(4) 0.069(2) Uani 1 1 d . . . H15 H -0.0359 0.1400 0.3381 0.083 Uiso 1 1 calc R . . C16 C 0.1171(10) 0.1976(7) 0.2741(4) 0.065(2) Uani 1 1 d . . . C17 C 0.2031(9) 0.2869(7) 0.2603(4) 0.061(2) Uani 1 1 d . . . H17 H 0.2634 0.2858 0.2213 0.073 Uiso 1 1 calc R . . C18 C 0.3060(10) 0.5923(6) 0.5278(4) 0.055(2) Uani 1 1 d . . . C19 C 0.4336(10) 0.6099(8) 0.5816(4) 0.083(3) Uani 1 1 d . . . H19A H 0.4863 0.5417 0.5883 0.124 Uiso 1 1 calc R . . H19B H 0.3964 0.6337 0.6264 0.124 Uiso 1 1 calc R . . H19C H 0.4984 0.6653 0.5639 0.124 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 Ni1 0.0837(8) 0.0512(6) 0.0375(5) 0.0093(4) 0.0102(5) -0.0088(5) Ni2 0.0796(11) 0.0455(8) 0.0343(7) 0.0086(6) 0.0119(7) -0.0022(7) Br1 0.1948(15) 0.0844(8) 0.1172(10) 0.0282(7) 0.0505(10) 0.0611(9) Br2 0.1299(10) 0.0731(7) 0.0651(6) -0.0215(5) 0.0014(6) -0.0052(6) O1 0.078(4) 0.045(3) 0.047(3) 0.010(2) 0.009(3) 0.003(3) O2 0.088(4) 0.042(3) 0.038(3) 0.002(2) 0.009(3) -0.007(3) O3 0.078(4) 0.066(3) 0.042(3) 0.007(3) 0.003(3) -0.008(3) O4 0.084(4) 0.059(3) 0.043(3) 0.010(3) 0.009(3) -0.003(3) N1 0.091(6) 0.058(4) 0.068(5) 0.015(4) 0.017(4) -0.021(4) N2 0.069(5) 0.074(5) 0.047(4) 0.006(3) 0.016(4) -0.016(4) C1 0.131(10) 0.047(5) 0.102(8) 0.018(5) 0.031(7) 0.008(6) C2 0.092(7) 0.056(5) 0.038(4) 0.005(4) 0.009(5) 0.001(5) C3 0.101(8) 0.053(5) 0.055(5) 0.011(4) 0.023(5) 0.011(5) C4 0.107(8) 0.071(6) 0.058(5) 0.010(5) 0.028(5) 0.017(6) C5 0.135(10) 0.057(6) 0.074(6) 0.018(5) 0.032(7) 0.022(6) C6 0.165(12) 0.054(6) 0.123(10) 0.029(6) 0.051(9) 0.003(8) C7 0.155(13) 0.048(7) 0.31(2) 0.009(9) 0.125(15) -0.017(7) C8 0.102(8) 0.064(6) 0.111(9) 0.025(6) 0.003(7) -0.015(6) C9 0.078(7) 0.105(8) 0.075(7) 0.042(6) 0.000(6) -0.026(6) C10 0.085(7) 0.097(7) 0.058(5) 0.006(5) 0.015(5) -0.025(6) C11 0.076(6) 0.078(6) 0.050(5) -0.003(4) 0.019(5) -0.010(5) C12 0.063(5) 0.053(5) 0.047(4) -0.001(4) 0.009(4) 0.000(4) C13 0.067(5) 0.047(4) 0.035(4) 0.005(3) 0.003(4) -0.001(4) C14 0.095(7) 0.054(5) 0.043(4) 0.004(4) 0.021(4) -0.005(5) C15 0.093(7) 0.053(5) 0.060(5) 0.004(4) 0.006(5) -0.012(5) C16 0.091(7) 0.055(5) 0.050(5) -0.008(4) 0.008(5) -0.008(5) C17 0.063(6) 0.072(6) 0.048(5) -0.003(4) 0.006(4) 0.009(5) C18 0.082(6) 0.040(4) 0.044(5) -0.001(3) 0.003(5) 0.008(4) C19 0.102(8) 0.098(7) 0.047(5) 0.009(5) -0.010(5) -0.007(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 Ni1 O1 1.986(5) . ? Ni1 O3 1.994(5) . ? Ni1 O2 1.998(5) . ? Ni1 N2 2.011(7) . ? Ni1 N1 2.049(7) . ? Ni2 O4 2.054(6) . ? Ni2 O4 2.054(6) 3_566 ? Ni2 O2 2.055(5) . ? Ni2 O2 2.055(5) 3_566 ? Ni2 O1 2.056(5) . ? Ni2 O1 2.056(5) 3_566 ? Br1 C5 1.893(10) . ? Br2 C16 1.896(8) . ? O1 C2 1.321(9) . ? O2 C13 1.320(8) . ? O3 C18 1.255(9) . ? O4 C18 1.228(9) . ? N1 C7 1.293(14) . ? N1 C8 1.475(12) . ? N2 C11 1.267(10) . ? N2 C10 1.480(10) . ? C1 C6 1.407(14) . ? C1 C2 1.426(12) . ? C1 C7 1.451(16) . ? C2 C3 1.387(12) . ? C3 C4 1.380(11) . ? C3 H3 0.9300 . ? C4 C5 1.365(12) . ? C4 H4 0.9300 . ? C5 C6 1.353(15) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.514(14) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.497(13) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.430(11) . ? C11 H11 0.9300 . ? C12 C13 1.403(10) . ? C12 C17 1.421(10) . ? C13 C14 1.397(10) . ? C14 C15 1.356(10) . ? C14 H14 0.9300 . ? C15 C16 1.371(11) . ? C15 H15 0.9300 . ? C16 C17 1.363(11) . ? C17 H17 0.9300 . ? C18 C19 1.525(11) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni1 O3 95.8(2) . . ? O1 Ni1 O2 81.7(2) . . ? O3 Ni1 O2 97.3(2) . . ? O1 Ni1 N2 166.1(3) . . ? O3 Ni1 N2 96.1(3) . . ? O2 Ni1 N2 89.7(2) . . ? O1 Ni1 N1 90.7(3) . . ? O3 Ni1 N1 95.4(3) . . ? O2 Ni1 N1 165.8(3) . . ? N2 Ni1 N1 95.3(3) . . ? O4 Ni2 O4 180.000(1) . 3_566 ? O4 Ni2 O2 87.9(2) . . ? O4 Ni2 O2 92.1(2) 3_566 . ? O4 Ni2 O2 92.1(2) . 3_566 ? O4 Ni2 O2 87.9(2) 3_566 3_566 ? O2 Ni2 O2 180.000(1) . 3_566 ? O4 Ni2 O1 87.0(2) . . ? O4 Ni2 O1 93.0(2) 3_566 . ? O2 Ni2 O1 78.70(19) . . ? O2 Ni2 O1 101.30(19) 3_566 . ? O4 Ni2 O1 93.0(2) . 3_566 ? O4 Ni2 O1 87.0(2) 3_566 3_566 ? O2 Ni2 O1 101.30(19) . 3_566 ? O2 Ni2 O1 78.70(19) 3_566 3_566 ? O1 Ni2 O1 180.000(1) . 3_566 ? C2 O1 Ni1 126.9(5) . . ? C2 O1 Ni2 134.8(5) . . ? Ni1 O1 Ni2 96.2(2) . . ? C13 O2 Ni1 127.3(4) . . ? C13 O2 Ni2 134.3(5) . . ? Ni1 O2 Ni2 95.8(2) . . ? C18 O3 Ni1 120.6(6) . . ? C18 O4 Ni2 133.2(5) . . ? C7 N1 C8 115.3(9) . . ? C7 N1 Ni1 116.2(7) . . ? C8 N1 Ni1 117.0(6) . . ? C11 N2 C10 116.7(7) . . ? C11 N2 Ni1 124.4(6) . . ? C10 N2 Ni1 118.7(6) . . ? C6 C1 C2 117.4(11) . . ? C6 C1 C7 121.4(10) . . ? C2 C1 C7 121.2(10) . . ? O1 C2 C3 123.4(7) . . ? O1 C2 C1 118.4(9) . . ? C3 C2 C1 118.1(9) . . ? C4 C3 C2 121.2(8) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 121.4(10) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 118.3(9) . . ? C6 C5 Br1 119.5(8) . . ? C4 C5 Br1 122.2(9) . . ? C5 C6 C1 123.4(10) . . ? C5 C6 H6 118.3 . . ? C1 C6 H6 118.3 . . ? N1 C7 C1 123.3(12) . . ? N1 C7 H7 118.3 . . ? C1 C7 H7 118.3 . . ? N1 C8 C9 111.6(8) . . ? N1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C10 C9 C8 115.4(8) . . ? C10 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? C8 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? N2 C10 C9 111.5(8) . . ? N2 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? N2 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? N2 C11 C12 127.3(8) . . ? N2 C11 H11 116.4 . . ? C12 C11 H11 116.4 . . ? C13 C12 C17 118.6(7) . . ? C13 C12 C11 125.4(7) . . ? C17 C12 C11 115.9(7) . . ? O2 C13 C14 120.6(7) . . ? O2 C13 C12 120.5(7) . . ? C14 C13 C12 118.9(7) . . ? C15 C14 C13 120.7(8) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 121.4(8) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 120.0(7) . . ? C17 C16 Br2 119.4(6) . . ? C15 C16 Br2 120.6(7) . . ? C16 C17 C12 120.4(8) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? O4 C18 O3 128.2(8) . . ? O4 C18 C19 117.5(7) . . ? O3 C18 C19 114.3(8) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.55 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.672 _refine_diff_density_min -1.032 _refine_diff_density_rms 0.097 data_3 #(CCDC 827066) _database_code_depnum_ccdc_archive 'CCDC 827066' #TrackingRef '- 5cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H34 Br4 Mn3 N4 O8' _chemical_formula_weight 1159.15 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' Mn Mn 0.3368 0.7283 '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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.328(2) _cell_length_b 22.468(5) _cell_length_c 8.2700(17) _cell_angle_alpha 90.00 _cell_angle_beta 93.74(3) _cell_angle_gamma 90.00 _cell_volume 2100.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2699 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1138 _exptl_absorpt_coefficient_mu 4.747 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3119 _exptl_absorpt_correction_T_max 0.3301 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'SMART CCD 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 16623 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4572 _reflns_number_gt 2987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.2250P] 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 4572 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Mn1 Mn 0.82968(5) 0.10798(2) 0.99444(8) 0.03237(16) Uani 1 1 d . . . Mn2 Mn 1.0000 0.0000 1.0000 0.0321(2) Uani 1 2 d S . . Br1 Br 0.42674(5) -0.11521(2) 0.55095(7) 0.0711(2) Uani 1 1 d . . . Br2 Br 1.34161(4) 0.24698(2) 0.58108(7) 0.05963(17) Uani 1 1 d . . . O1 O 0.8129(2) 0.01682(11) 0.9355(3) 0.0396(7) Uani 1 1 d . . . O2 O 1.0002(2) 0.09369(11) 0.9215(3) 0.0382(7) Uani 1 1 d . . . O3 O 0.8588(3) 0.11872(14) 1.2406(4) 0.0559(9) Uani 1 1 d . . . O4 O 0.9592(3) 0.03424(13) 1.2369(3) 0.0494(8) Uani 1 1 d . . . N1 N 0.6407(3) 0.11234(14) 0.9402(4) 0.0381(8) Uani 1 1 d . . . N2 N 0.8482(3) 0.19904(13) 0.9097(4) 0.0358(8) Uani 1 1 d . . . C1 C 0.6118(4) 0.01268(17) 0.8295(5) 0.0396(10) Uani 1 1 d . . . C2 C 0.7266(3) -0.01175(17) 0.8552(5) 0.0353(9) Uani 1 1 d . . . C3 C 0.7456(4) -0.06878(17) 0.7910(5) 0.0425(11) Uani 1 1 d . . . H3 H 0.8200 -0.0861 0.8082 0.051 Uiso 1 1 calc R . . C4 C 0.6588(4) -0.09963(19) 0.7045(6) 0.0469(11) Uani 1 1 d . . . H4 H 0.6742 -0.1373 0.6640 0.056 Uiso 1 1 calc R . . C5 C 0.5483(4) -0.07453(18) 0.6777(6) 0.0477(12) Uani 1 1 d . . . C6 C 0.5235(4) -0.02018(19) 0.7400(6) 0.0493(12) Uani 1 1 d . . . H6 H 0.4477 -0.0045 0.7234 0.059 Uiso 1 1 calc R . . C7 C 0.5769(4) 0.07108(18) 0.8826(6) 0.0464(12) Uani 1 1 d . . . H7 H 0.4961 0.0790 0.8726 0.056 Uiso 1 1 calc R . . C8 C 0.5828(4) 0.16854(18) 0.9771(6) 0.0454(11) Uani 1 1 d . . . H8A H 0.5941 0.1763 1.0925 0.055 Uiso 1 1 calc R . . H8B H 0.4985 0.1650 0.9499 0.055 Uiso 1 1 calc R . . C9 C 0.6311(4) 0.22026(18) 0.8848(6) 0.0439(11) Uani 1 1 d . . . H9A H 0.5764 0.2533 0.8902 0.053 Uiso 1 1 calc R . . H9B H 0.6326 0.2088 0.7719 0.053 Uiso 1 1 calc R . . C10 C 0.7533(4) 0.24206(17) 0.9416(6) 0.0451(11) Uani 1 1 d . . . H10A H 0.7688 0.2793 0.8873 0.054 Uiso 1 1 calc R . . H10B H 0.7551 0.2499 1.0570 0.054 Uiso 1 1 calc R . . C11 C 0.9402(4) 0.22016(18) 0.8495(5) 0.0428(11) Uani 1 1 d . . . H11 H 0.9392 0.2609 0.8289 0.051 Uiso 1 1 calc R . . C12 C 1.0462(3) 0.18865(17) 0.8091(5) 0.0363(10) Uani 1 1 d . . . C13 C 1.0718(3) 0.12843(16) 0.8447(5) 0.0314(9) Uani 1 1 d . . . C14 C 1.1778(4) 0.10500(18) 0.7921(5) 0.0404(10) Uani 1 1 d . . . H14 H 1.1955 0.0652 0.8123 0.048 Uiso 1 1 calc R . . C15 C 1.2561(4) 0.13890(19) 0.7121(5) 0.0420(10) Uani 1 1 d . . . H15 H 1.3255 0.1221 0.6789 0.050 Uiso 1 1 calc R . . C16 C 1.2310(4) 0.19800(18) 0.6814(5) 0.0380(10) Uani 1 1 d . . . C17 C 1.1282(4) 0.22305(18) 0.7291(5) 0.0406(10) Uani 1 1 d . . . H17 H 1.1128 0.2631 0.7084 0.049 Uiso 1 1 calc R . . C18 C 0.9150(4) 0.0764(2) 1.3093(5) 0.0479(12) Uani 1 1 d . . . C19 C 0.9297(7) 0.0784(3) 1.4911(6) 0.110(3) Uani 1 1 d . . . H19A H 0.9047 0.1165 1.5286 0.164 Uiso 1 1 calc R . . H19B H 1.0114 0.0722 1.5254 0.164 Uiso 1 1 calc R . . H19C H 0.8825 0.0477 1.5354 0.164 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 Mn1 0.0304(3) 0.0265(3) 0.0401(4) 0.0021(3) 0.0015(3) 0.0042(2) Mn2 0.0296(5) 0.0260(5) 0.0403(5) 0.0036(4) -0.0002(4) 0.0069(3) Br1 0.0729(4) 0.0498(3) 0.0864(4) -0.0022(3) -0.0260(3) -0.0217(3) Br2 0.0523(3) 0.0599(3) 0.0689(4) 0.0084(3) 0.0211(3) -0.0148(2) O1 0.0300(15) 0.0281(15) 0.0592(19) -0.0054(13) -0.0087(14) 0.0033(12) O2 0.0335(15) 0.0270(15) 0.0556(19) 0.0118(13) 0.0135(14) 0.0062(12) O3 0.068(2) 0.058(2) 0.0408(19) 0.0003(15) -0.0055(16) 0.0217(17) O4 0.060(2) 0.0464(19) 0.0421(18) -0.0062(14) 0.0039(15) 0.0091(15) N1 0.035(2) 0.0269(18) 0.052(2) -0.0036(16) 0.0035(17) 0.0040(15) N2 0.0332(19) 0.0284(18) 0.046(2) 0.0054(15) 0.0068(16) 0.0065(14) C1 0.037(2) 0.029(2) 0.052(3) 0.0004(19) -0.004(2) 0.0035(18) C2 0.036(2) 0.030(2) 0.039(2) 0.0032(18) -0.0025(19) 0.0033(18) C3 0.044(3) 0.029(2) 0.054(3) -0.004(2) 0.001(2) 0.0085(19) C4 0.054(3) 0.031(2) 0.056(3) 0.001(2) 0.000(2) 0.001(2) C5 0.057(3) 0.034(2) 0.051(3) 0.001(2) -0.012(2) -0.016(2) C6 0.036(3) 0.041(3) 0.069(3) 0.003(2) -0.006(2) -0.002(2) C7 0.028(2) 0.040(3) 0.071(3) -0.001(2) 0.003(2) 0.0031(19) C8 0.035(2) 0.039(3) 0.064(3) -0.010(2) 0.014(2) 0.0055(19) C9 0.039(2) 0.034(2) 0.059(3) 0.001(2) 0.004(2) 0.0159(19) C10 0.046(3) 0.030(2) 0.061(3) 0.001(2) 0.013(2) 0.0092(19) C11 0.045(3) 0.024(2) 0.060(3) 0.006(2) 0.007(2) 0.0035(19) C12 0.036(2) 0.031(2) 0.043(3) 0.0007(18) 0.005(2) -0.0031(18) C13 0.029(2) 0.032(2) 0.033(2) 0.0019(17) -0.0003(17) -0.0030(17) C14 0.036(2) 0.037(2) 0.048(3) 0.010(2) 0.003(2) 0.0070(19) C15 0.032(2) 0.053(3) 0.041(3) 0.002(2) 0.004(2) 0.006(2) C16 0.036(2) 0.040(2) 0.038(2) 0.0020(19) 0.0040(19) -0.0065(19) C17 0.047(3) 0.024(2) 0.052(3) 0.0044(19) 0.006(2) -0.0047(19) C18 0.049(3) 0.057(3) 0.037(3) -0.003(2) -0.004(2) 0.005(2) C19 0.171(7) 0.116(5) 0.039(3) -0.021(3) -0.018(4) 0.078(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O3 2.056(3) . ? Mn1 O2 2.085(3) . ? Mn1 O1 2.111(3) . ? Mn1 N1 2.160(3) . ? Mn1 N2 2.177(3) . ? Mn2 O4 2.182(3) . ? Mn2 O4 2.182(3) 3_757 ? Mn2 O1 2.185(3) 3_757 ? Mn2 O1 2.185(3) . ? Mn2 O2 2.203(2) . ? Mn2 O2 2.203(2) 3_757 ? Br1 C5 1.909(4) . ? Br2 C16 1.899(4) . ? O1 C2 1.313(4) . ? O2 C13 1.319(4) . ? O3 C18 1.258(5) . ? O4 C18 1.244(5) . ? N1 C7 1.251(5) . ? N1 C8 1.464(5) . ? N2 C11 1.275(5) . ? N2 C10 1.482(5) . ? C1 C6 1.413(6) . ? C1 C2 1.415(5) . ? C1 C7 1.447(6) . ? C2 C3 1.409(5) . ? C3 C4 1.367(6) . ? C3 H3 0.9300 . ? C4 C5 1.378(6) . ? C4 H4 0.9300 . ? C5 C6 1.362(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.512(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.514(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.451(6) . ? C11 H11 0.9300 . ? C12 C17 1.407(5) . ? C12 C13 1.411(5) . ? C13 C14 1.406(5) . ? C14 C15 1.371(6) . ? C14 H14 0.9300 . ? C15 C16 1.378(5) . ? C15 H15 0.9300 . ? C16 C17 1.373(6) . ? C17 H17 0.9300 . ? C18 C19 1.502(7) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O3 Mn1 O2 102.29(13) . . ? O3 Mn1 O1 110.43(12) . . ? O2 Mn1 O1 81.67(10) . . ? O3 Mn1 N1 107.04(14) . . ? O2 Mn1 N1 150.54(12) . . ? O1 Mn1 N1 85.58(11) . . ? O3 Mn1 N2 101.29(13) . . ? O2 Mn1 N2 86.63(11) . . ? O1 Mn1 N2 147.83(12) . . ? N1 Mn1 N2 90.31(12) . . ? O4 Mn2 O4 180.0 . 3_757 ? O4 Mn2 O1 95.78(11) . 3_757 ? O4 Mn2 O1 84.22(11) 3_757 3_757 ? O4 Mn2 O1 84.22(11) . . ? O4 Mn2 O1 95.78(11) 3_757 . ? O1 Mn2 O1 180.0 3_757 . ? O4 Mn2 O2 86.10(11) . . ? O4 Mn2 O2 93.90(11) 3_757 . ? O1 Mn2 O2 102.58(10) 3_757 . ? O1 Mn2 O2 77.42(10) . . ? O4 Mn2 O2 93.90(11) . 3_757 ? O4 Mn2 O2 86.10(11) 3_757 3_757 ? O1 Mn2 O2 77.42(10) 3_757 3_757 ? O1 Mn2 O2 102.58(10) . 3_757 ? O2 Mn2 O2 180.00(4) . 3_757 ? C2 O1 Mn1 130.1(2) . . ? C2 O1 Mn2 135.8(2) . . ? Mn1 O1 Mn2 92.29(10) . . ? C13 O2 Mn1 131.2(2) . . ? C13 O2 Mn2 136.1(2) . . ? Mn1 O2 Mn2 92.48(10) . . ? C18 O3 Mn1 113.7(3) . . ? C18 O4 Mn2 144.7(3) . . ? C7 N1 C8 117.5(3) . . ? C7 N1 Mn1 125.9(3) . . ? C8 N1 Mn1 116.6(3) . . ? C11 N2 C10 116.6(3) . . ? C11 N2 Mn1 125.0(3) . . ? C10 N2 Mn1 118.0(3) . . ? C6 C1 C2 119.2(4) . . ? C6 C1 C7 115.8(4) . . ? C2 C1 C7 124.9(4) . . ? O1 C2 C3 120.5(3) . . ? O1 C2 C1 122.2(3) . . ? C3 C2 C1 117.2(4) . . ? C4 C3 C2 122.4(4) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 119.5(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.9(4) . . ? C6 C5 Br1 118.5(3) . . ? C4 C5 Br1 120.5(3) . . ? C5 C6 C1 120.7(4) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N1 C7 C1 128.7(4) . . ? N1 C7 H7 115.7 . . ? C1 C7 H7 115.7 . . ? N1 C8 C9 112.1(3) . . ? N1 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? N1 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 116.5(4) . . ? C8 C9 H9A 108.2 . . ? C10 C9 H9A 108.2 . . ? C8 C9 H9B 108.2 . . ? C10 C9 H9B 108.2 . . ? H9A C9 H9B 107.3 . . ? N2 C10 C9 113.1(3) . . ? N2 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? N2 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? N2 C11 C12 128.1(4) . . ? N2 C11 H11 115.9 . . ? C12 C11 H11 115.9 . . ? C17 C12 C13 119.5(4) . . ? C17 C12 C11 115.0(4) . . ? C13 C12 C11 125.6(4) . . ? O2 C13 C14 119.5(3) . . ? O2 C13 C12 122.9(3) . . ? C14 C13 C12 117.6(4) . . ? C15 C14 C13 122.2(4) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C14 C15 C16 119.5(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 120.7(4) . . ? C17 C16 Br2 118.9(3) . . ? C15 C16 Br2 120.3(3) . . ? C16 C17 C12 120.5(4) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? O4 C18 O3 124.4(4) . . ? O4 C18 C19 118.8(4) . . ? O3 C18 C19 116.7(4) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.488 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.087