# 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 _publ_contact_author_name 'Liya Wang' _publ_contact_author_address ; ; _publ_contact_author_email wlya@lynu.edu.cn loop_ _publ_author_name 'Lufang Ma' 'Xiuqin Li' 'Liya Wang' 'Hongwei Hou' # Attachment '- 3.cif' data_bb3 _database_code_depnum_ccdc_archive 'CCDC 796638' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 Br Co N4 O4' _chemical_formula_weight 478.17 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' Co Co 0.3494 0.9721 '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)/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 10.093(3) _cell_length_b 20.139(5) _cell_length_c 9.676(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.269(3) _cell_angle_gamma 90.00 _cell_volume 1921.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2701 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 24.68 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_absorpt_coefficient_mu 3.002 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5207 _exptl_absorpt_correction_T_max 0.5993 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13016 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3516 _reflns_number_gt 2443 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.6109P] 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 3516 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 Co1 Co 0.84084(5) 0.05914(2) 1.07116(6) 0.02906(17) Uani 1 1 d . . . Br1 Br 0.61333(6) -0.26292(3) 0.54502(7) 0.0773(3) Uani 1 1 d . . . O1 O 0.9660(3) -0.09182(13) 0.8474(3) 0.0359(7) Uani 1 1 d . . . O2 O 0.8503(3) -0.01217(15) 0.9253(3) 0.0504(8) Uani 1 1 d . . . O3 O 0.3709(3) -0.06051(14) 0.9448(3) 0.0397(7) Uani 1 1 d . . . O4 O 0.2538(3) -0.13115(14) 0.7944(3) 0.0410(7) Uani 1 1 d . . . N1 N 0.8246(3) 0.13002(17) 0.9054(4) 0.0385(8) Uani 1 1 d . . . N2 N 0.8857(4) 0.19033(16) 0.7387(4) 0.0398(9) Uani 1 1 d . . . N3 N 1.0591(4) 0.08498(17) 0.5991(4) 0.0431(9) Uani 1 1 d . . . N4 N 1.1445(4) 0.01455(16) 0.7679(4) 0.0416(9) Uani 1 1 d . . . C1 C 0.7286(4) -0.10332(17) 0.8118(4) 0.0258(8) Uani 1 1 d . . . C2 C 0.6086(4) -0.08547(18) 0.8508(4) 0.0281(9) Uani 1 1 d . . . H2 H 0.6076 -0.0497 0.9113 0.034 Uiso 1 1 calc R . . C3 C 0.4904(4) -0.12073(18) 0.7998(4) 0.0273(8) Uani 1 1 d . . . C4 C 0.4910(4) -0.17304(19) 0.7065(4) 0.0339(9) Uani 1 1 d . . . H4 H 0.4116 -0.1962 0.6698 0.041 Uiso 1 1 calc R . . C5 C 0.6106(4) -0.1901(2) 0.6690(4) 0.0375(10) Uani 1 1 d . . . C6 C 0.7299(4) -0.15678(18) 0.7210(4) 0.0324(9) Uani 1 1 d . . . H6 H 0.8100 -0.1698 0.6958 0.039 Uiso 1 1 calc R . . C7 C 0.8575(4) -0.06623(18) 0.8663(4) 0.0276(8) Uani 1 1 d . . . C8 C 0.3633(4) -0.10332(19) 0.8494(4) 0.0307(9) Uani 1 1 d . . . C9 C 0.9270(5) 0.15226(19) 0.8539(4) 0.0379(10) Uani 1 1 d . . . H9 H 1.0174 0.1427 0.8927 0.045 Uiso 1 1 calc R . . C10 C 0.7129(5) 0.1556(3) 0.8180(5) 0.0565(13) Uani 1 1 d . . . H10 H 0.6242 0.1486 0.8276 0.068 Uiso 1 1 calc R . . C11 C 0.7487(5) 0.1925(3) 0.7155(5) 0.0585(14) Uani 1 1 d . . . H11 H 0.6906 0.2151 0.6432 0.070 Uiso 1 1 calc R . . C12 C 0.9736(5) 0.2224(2) 0.6584(5) 0.0486(12) Uani 1 1 d . . . H12A H 1.0669 0.2175 0.7092 0.058 Uiso 1 1 calc R . . H12B H 0.9531 0.2695 0.6521 0.058 Uiso 1 1 calc R . . C13 C 0.9605(5) 0.1949(2) 0.5099(5) 0.0484(12) Uani 1 1 d . . . H13A H 0.8787 0.2131 0.4509 0.058 Uiso 1 1 calc R . . H13B H 1.0366 0.2109 0.4729 0.058 Uiso 1 1 calc R . . C14 C 0.9550(5) 0.1199(2) 0.4953(5) 0.0497(12) Uani 1 1 d . . . H14A H 0.8664 0.1047 0.5053 0.060 Uiso 1 1 calc R . . H14B H 0.9655 0.1082 0.4010 0.060 Uiso 1 1 calc R . . C15 C 1.0344(5) 0.0369(2) 0.6853(4) 0.0394(10) Uani 1 1 d . . . H15 H 0.9480 0.0211 0.6862 0.047 Uiso 1 1 calc R . . C16 C 1.2481(5) 0.0512(3) 0.7332(6) 0.0698(17) Uani 1 1 d . . . H16 H 1.3398 0.0468 0.7742 0.084 Uiso 1 1 calc R . . C17 C 1.1943(6) 0.0946(3) 0.6296(6) 0.0723(17) Uani 1 1 d . . . H17 H 1.2418 0.1254 0.5872 0.087 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 Co1 0.0194(3) 0.0295(3) 0.0407(3) -0.0045(2) 0.0119(2) -0.0015(2) Br1 0.0560(4) 0.0794(4) 0.1040(5) -0.0635(3) 0.0341(3) -0.0202(3) O1 0.0184(15) 0.0381(16) 0.0530(18) -0.0061(13) 0.0115(13) -0.0008(12) O2 0.0303(18) 0.0481(19) 0.075(2) -0.0305(16) 0.0157(15) -0.0068(14) O3 0.0264(16) 0.0448(17) 0.0513(18) -0.0112(14) 0.0160(13) 0.0002(13) O4 0.0210(16) 0.0498(17) 0.0525(18) -0.0052(14) 0.0086(13) -0.0041(13) N1 0.031(2) 0.046(2) 0.041(2) -0.0006(16) 0.0126(17) 0.0045(16) N2 0.049(3) 0.036(2) 0.036(2) 0.0011(15) 0.0128(17) 0.0070(16) N3 0.048(3) 0.038(2) 0.046(2) 0.0033(17) 0.0161(19) 0.0031(17) N4 0.038(2) 0.035(2) 0.056(2) 0.0049(17) 0.0194(19) 0.0010(16) C1 0.020(2) 0.027(2) 0.031(2) 0.0011(16) 0.0077(16) 0.0016(15) C2 0.026(2) 0.0260(19) 0.035(2) -0.0017(16) 0.0128(18) 0.0010(16) C3 0.020(2) 0.029(2) 0.034(2) 0.0021(16) 0.0088(17) 0.0003(15) C4 0.021(2) 0.042(2) 0.040(2) -0.0071(18) 0.0090(18) -0.0093(17) C5 0.034(3) 0.040(2) 0.043(3) -0.0124(19) 0.018(2) -0.0038(18) C6 0.022(2) 0.037(2) 0.041(2) -0.0073(18) 0.0133(18) 0.0007(17) C7 0.022(2) 0.032(2) 0.030(2) -0.0005(17) 0.0105(17) 0.0002(16) C8 0.023(2) 0.029(2) 0.041(2) 0.0044(18) 0.0094(18) 0.0012(16) C9 0.038(3) 0.035(2) 0.042(3) -0.0030(19) 0.013(2) 0.0019(19) C10 0.036(3) 0.071(3) 0.063(3) 0.008(3) 0.010(2) 0.010(2) C11 0.049(4) 0.072(3) 0.055(3) 0.020(3) 0.012(3) 0.021(3) C12 0.064(3) 0.040(3) 0.046(3) 0.006(2) 0.020(2) -0.005(2) C13 0.061(3) 0.043(3) 0.044(3) 0.008(2) 0.018(2) 0.002(2) C14 0.062(3) 0.047(3) 0.040(3) 0.001(2) 0.011(2) 0.008(2) C15 0.040(3) 0.032(2) 0.049(3) 0.0017(19) 0.017(2) 0.0004(19) C16 0.034(3) 0.075(4) 0.101(4) 0.037(3) 0.017(3) -0.002(3) C17 0.056(4) 0.068(4) 0.099(5) 0.041(3) 0.031(3) 0.001(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 Co1 O2 2.030(3) . ? Co1 O1 2.049(3) 3_757 ? Co1 O3 2.109(3) 3_657 ? Co1 N1 2.127(3) . ? Co1 N4 2.133(3) 3_757 ? Co1 O4 2.289(3) 3_657 ? Co1 C8 2.510(4) 3_657 ? Br1 C5 1.899(4) . ? O1 C7 1.259(4) . ? O1 Co1 2.049(3) 3_757 ? O2 C7 1.238(4) . ? O3 C8 1.253(5) . ? O3 Co1 2.109(3) 3_657 ? O4 C8 1.253(5) . ? O4 Co1 2.289(3) 3_657 ? N1 C9 1.318(5) . ? N1 C10 1.359(6) . ? N2 C9 1.344(5) . ? N2 C11 1.354(6) . ? N2 C12 1.449(5) . ? N3 C15 1.336(5) . ? N3 C17 1.347(6) . ? N3 C14 1.470(6) . ? N4 C15 1.303(5) . ? N4 C16 1.379(6) . ? N4 Co1 2.133(3) 3_757 ? C1 C2 1.390(5) . ? C1 C6 1.391(5) . ? C1 C7 1.496(5) . ? C2 C3 1.385(5) . ? C2 H2 0.9300 . ? C3 C4 1.389(5) . ? C3 C8 1.503(5) . ? C4 C5 1.376(5) . ? C4 H4 0.9300 . ? C5 C6 1.376(5) . ? C6 H6 0.9300 . ? C8 Co1 2.510(4) 3_657 ? C9 H9 0.9300 . ? C10 C11 1.349(7) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.519(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.516(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15 0.9300 . ? C16 C17 1.355(7) . ? C16 H16 0.9300 . ? 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 Co1 O1 108.24(11) . 3_757 ? O2 Co1 O3 98.91(11) . 3_657 ? O1 Co1 O3 152.84(11) 3_757 3_657 ? O2 Co1 N1 87.59(14) . . ? O1 Co1 N1 89.35(12) 3_757 . ? O3 Co1 N1 91.24(12) 3_657 . ? O2 Co1 N4 90.52(14) . 3_757 ? O1 Co1 N4 91.71(12) 3_757 3_757 ? O3 Co1 N4 88.56(13) 3_657 3_757 ? N1 Co1 N4 178.04(13) . 3_757 ? O2 Co1 O4 158.53(11) . 3_657 ? O1 Co1 O4 93.20(10) 3_757 3_657 ? O3 Co1 O4 59.64(10) 3_657 3_657 ? N1 Co1 O4 91.66(12) . 3_657 ? N4 Co1 O4 89.92(12) 3_757 3_657 ? O2 Co1 C8 128.80(13) . 3_657 ? O1 Co1 C8 122.96(12) 3_757 3_657 ? O3 Co1 C8 29.91(11) 3_657 3_657 ? N1 Co1 C8 93.23(12) . 3_657 ? N4 Co1 C8 87.57(13) 3_757 3_657 ? O4 Co1 C8 29.81(11) 3_657 3_657 ? C7 O1 Co1 126.8(2) . 3_757 ? C7 O2 Co1 163.4(3) . . ? C8 O3 Co1 93.0(2) . 3_657 ? C8 O4 Co1 84.9(2) . 3_657 ? C9 N1 C10 104.4(4) . . ? C9 N1 Co1 124.9(3) . . ? C10 N1 Co1 130.1(3) . . ? C9 N2 C11 106.4(4) . . ? C9 N2 C12 125.5(4) . . ? C11 N2 C12 128.1(4) . . ? C15 N3 C17 106.4(4) . . ? C15 N3 C14 124.9(4) . . ? C17 N3 C14 128.6(4) . . ? C15 N4 C16 104.9(4) . . ? C15 N4 Co1 127.3(3) . 3_757 ? C16 N4 Co1 127.7(3) . 3_757 ? C2 C1 C6 119.8(3) . . ? C2 C1 C7 121.2(3) . . ? C6 C1 C7 119.0(3) . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 C8 119.7(3) . . ? C4 C3 C8 120.4(3) . . ? C5 C4 C3 119.1(4) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 122.0(4) . . ? C4 C5 Br1 119.4(3) . . ? C6 C5 Br1 118.6(3) . . ? C5 C6 C1 118.9(4) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? O2 C7 O1 124.4(4) . . ? O2 C7 C1 118.0(3) . . ? O1 C7 C1 117.6(3) . . ? O4 C8 O3 122.1(4) . . ? O4 C8 C3 119.7(4) . . ? O3 C8 C3 118.2(3) . . ? O4 C8 Co1 65.3(2) . 3_657 ? O3 C8 Co1 57.05(19) . 3_657 ? C3 C8 Co1 172.7(3) . 3_657 ? N1 C9 N2 112.2(4) . . ? N1 C9 H9 123.9 . . ? N2 C9 H9 123.9 . . ? C11 C10 N1 110.5(4) . . ? C11 C10 H10 124.8 . . ? N1 C10 H10 124.8 . . ? C10 C11 N2 106.5(4) . . ? C10 C11 H11 126.8 . . ? N2 C11 H11 126.8 . . ? N2 C12 C13 113.8(4) . . ? N2 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N2 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 116.4(4) . . ? C14 C13 H13A 108.2 . . ? C12 C13 H13A 108.2 . . ? C14 C13 H13B 108.2 . . ? C12 C13 H13B 108.2 . . ? H13A C13 H13B 107.3 . . ? N3 C14 C13 114.0(4) . . ? N3 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? N3 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.6 . . ? N4 C15 N3 112.7(4) . . ? N4 C15 H15 123.7 . . ? N3 C15 H15 123.7 . . ? C17 C16 N4 108.7(5) . . ? C17 C16 H16 125.7 . . ? N4 C16 H16 125.7 . . ? N3 C17 C16 107.3(4) . . ? N3 C17 H17 126.4 . . ? C16 C17 H17 126.4 . . ? 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 O1 Co1 O2 C7 93.3(10) 3_757 . . . ? O3 Co1 O2 C7 -87.3(10) 3_657 . . . ? N1 Co1 O2 C7 -178.2(10) . . . . ? N4 Co1 O2 C7 1.3(10) 3_757 . . . ? O4 Co1 O2 C7 -89.8(10) 3_657 . . . ? C8 Co1 O2 C7 -86.0(10) 3_657 . . . ? O2 Co1 N1 C9 -79.1(3) . . . . ? O1 Co1 N1 C9 29.2(3) 3_757 . . . ? O3 Co1 N1 C9 -178.0(3) 3_657 . . . ? N4 Co1 N1 C9 -94(4) 3_757 . . . ? O4 Co1 N1 C9 122.4(3) 3_657 . . . ? C8 Co1 N1 C9 152.2(3) 3_657 . . . ? O2 Co1 N1 C10 91.4(4) . . . . ? O1 Co1 N1 C10 -160.3(4) 3_757 . . . ? O3 Co1 N1 C10 -7.5(4) 3_657 . . . ? N4 Co1 N1 C10 77(4) 3_757 . . . ? O4 Co1 N1 C10 -67.2(4) 3_657 . . . ? C8 Co1 N1 C10 -37.4(4) 3_657 . . . ? C6 C1 C2 C3 0.1(6) . . . . ? C7 C1 C2 C3 -179.6(3) . . . . ? C1 C2 C3 C4 -1.7(6) . . . . ? C1 C2 C3 C8 176.5(3) . . . . ? C2 C3 C4 C5 1.7(6) . . . . ? C8 C3 C4 C5 -176.5(4) . . . . ? C3 C4 C5 C6 -0.2(6) . . . . ? C3 C4 C5 Br1 178.5(3) . . . . ? C4 C5 C6 C1 -1.4(6) . . . . ? Br1 C5 C6 C1 179.9(3) . . . . ? C2 C1 C6 C5 1.4(6) . . . . ? C7 C1 C6 C5 -178.9(4) . . . . ? Co1 O2 C7 O1 -95.0(10) . . . . ? Co1 O2 C7 C1 86.0(10) . . . . ? Co1 O1 C7 O2 8.6(6) 3_757 . . . ? Co1 O1 C7 C1 -172.4(2) 3_757 . . . ? C2 C1 C7 O2 -13.2(5) . . . . ? C6 C1 C7 O2 167.1(4) . . . . ? C2 C1 C7 O1 167.7(3) . . . . ? C6 C1 C7 O1 -12.0(5) . . . . ? Co1 O4 C8 O3 5.4(4) 3_657 . . . ? Co1 O4 C8 C3 -174.0(3) 3_657 . . . ? Co1 O3 C8 O4 -5.8(4) 3_657 . . . ? Co1 O3 C8 C3 173.6(3) 3_657 . . . ? C2 C3 C8 O4 173.8(3) . . . . ? C4 C3 C8 O4 -8.0(6) . . . . ? C2 C3 C8 O3 -5.6(5) . . . . ? C4 C3 C8 O3 172.6(4) . . . . ? C2 C3 C8 Co1 42(2) . . . 3_657 ? C4 C3 C8 Co1 -139(2) . . . 3_657 ? C10 N1 C9 N2 -0.1(5) . . . . ? Co1 N1 C9 N2 172.3(3) . . . . ? C11 N2 C9 N1 0.1(5) . . . . ? C12 N2 C9 N1 179.6(4) . . . . ? C9 N1 C10 C11 0.1(5) . . . . ? Co1 N1 C10 C11 -171.8(3) . . . . ? N1 C10 C11 N2 -0.1(6) . . . . ? C9 N2 C11 C10 0.0(5) . . . . ? C12 N2 C11 C10 -179.5(4) . . . . ? C9 N2 C12 C13 113.0(5) . . . . ? C11 N2 C12 C13 -67.6(6) . . . . ? N2 C12 C13 C14 -44.2(6) . . . . ? C15 N3 C14 C13 125.9(4) . . . . ? C17 N3 C14 C13 -52.7(7) . . . . ? C12 C13 C14 N3 -46.9(6) . . . . ? C16 N4 C15 N3 0.4(5) . . . . ? Co1 N4 C15 N3 177.5(3) 3_757 . . . ? C17 N3 C15 N4 -0.6(5) . . . . ? C14 N3 C15 N4 -179.4(4) . . . . ? C15 N4 C16 C17 0.0(6) . . . . ? Co1 N4 C16 C17 -177.1(4) 3_757 . . . ? C15 N3 C17 C16 0.6(6) . . . . ? C14 N3 C17 C16 179.4(5) . . . . ? N4 C16 C17 N3 -0.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.905 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.094 data_b _database_code_depnum_ccdc_archive 'CCDC 796639' #TrackingRef '796641.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 Br Co N4 O4' _chemical_formula_weight 478.17 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' Co Co 0.3494 0.9721 '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 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' _cell_length_a 18.519(8) _cell_length_b 13.366(6) _cell_length_c 7.971(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.072(5) _cell_angle_gamma 90.00 _cell_volume 1815.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3011 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 24.48 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.750 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_absorpt_coefficient_mu 3.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5038 _exptl_absorpt_correction_T_max 0.5834 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6741 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3289 _reflns_number_gt 2980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1220P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.042(18) _refine_ls_number_reflns 3289 _refine_ls_number_parameters 247 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1649 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Co1 Co 0.79281(4) 0.16882(7) 0.61246(10) 0.0342(3) Uani 1 1 d . . . N1 N 0.7648(4) 0.1197(5) 0.3557(8) 0.0401(13) Uani 1 1 d . . . N2 N 0.7352(3) 0.0183(5) 0.1223(7) 0.0390(13) Uani 1 1 d . . . N3 N 0.4997(4) -0.1682(4) -0.2527(9) 0.0394(12) Uani 1 1 d . . . N4 N 0.3792(3) -0.2274(5) -0.3497(7) 0.0377(12) Uani 1 1 d . . . O1 O 0.7087(3) 0.2488(5) 0.6318(7) 0.0511(13) Uani 1 1 d . . . O2 O 0.6455(3) 0.1048(4) 0.5833(9) 0.0567(15) Uani 1 1 d . . . O3 O 0.8624(3) 0.0780(4) 0.7956(7) 0.0469(12) Uani 1 1 d . . . O4 O 0.7968(3) -0.0637(5) 0.7031(8) 0.0531(13) Uani 1 1 d . . . Br1 Br 0.5000 0.54936(9) 0.5000 0.0828(5) Uani 1 2 d S . . Br2 Br 1.0000 -0.36849(9) 1.0000 0.0847(5) Uani 1 2 d S . . C1 C 0.5000 0.4069(8) 0.5000 0.044(2) Uani 1 2 d S . . C2 C 0.5700(4) 0.3578(5) 0.5460(10) 0.0390(15) Uani 1 1 d . . . H2 H 0.6167 0.3933 0.5769 0.047 Uiso 1 1 calc R . . C3 C 0.5699(4) 0.2527(6) 0.5455(8) 0.0356(14) Uani 1 1 d . . . C4 C 0.5000 0.2010(6) 0.5000 0.0320(18) Uani 1 2 d S . . H4 H 0.5000 0.1314 0.5000 0.038 Uiso 1 2 calc SR . . C5 C 0.6451(4) 0.1952(6) 0.5891(9) 0.0413(16) Uani 1 1 d . . . C6 C 1.0000 -0.2269(8) 1.0000 0.044(2) Uani 1 2 d S . . C7 C 0.9312(4) -0.1755(6) 0.9014(10) 0.0434(16) Uani 1 1 d . . . H7 H 0.8853 -0.2105 0.8359 0.052 Uiso 1 1 calc R . . C8 C 0.9312(4) -0.0723(5) 0.9012(8) 0.0349(13) Uani 1 1 d . . . C9 C 1.0000 -0.0218(8) 1.0000 0.0347(19) Uani 1 2 d S . . H9 H 1.0000 0.0478 1.0000 0.042 Uiso 1 2 calc SR . . C10 C 0.8571(4) -0.0179(6) 0.7897(9) 0.0392(15) Uani 1 1 d . . . C11 C 0.7559(5) 0.1740(7) 0.2048(10) 0.0541(18) Uani 1 1 d . . . H11 H 0.7630 0.2428 0.2030 0.065 Uiso 1 1 calc R . . C12 C 0.7354(5) 0.1137(6) 0.0581(11) 0.052(2) Uani 1 1 d . . . H12 H 0.7237 0.1327 -0.0619 0.063 Uiso 1 1 calc R . . C13 C 0.7515(3) 0.0246(5) 0.3007(9) 0.0347(14) Uani 1 1 d . . . H13 H 0.7533 -0.0294 0.3758 0.042 Uiso 1 1 calc R . . C14 C 0.7079(4) -0.0729(7) 0.0134(11) 0.0465(17) Uani 1 1 d . . . H14A H 0.7284 -0.1313 0.0895 0.056 Uiso 1 1 calc R . . H14B H 0.7266 -0.0741 -0.0844 0.056 Uiso 1 1 calc R . . C15 C 0.6176(4) -0.0750(7) -0.0666(12) 0.0516(18) Uani 1 1 d . . . H15A H 0.5993 -0.0695 0.0317 0.062 Uiso 1 1 calc R . . H15B H 0.5977 -0.0179 -0.1465 0.062 Uiso 1 1 calc R . . C16 C 0.5856(4) -0.1701(6) -0.1724(10) 0.0434(16) Uani 1 1 d . . . H16A H 0.6052 -0.1770 -0.2683 0.052 Uiso 1 1 calc R . . H16B H 0.6036 -0.2272 -0.0917 0.052 Uiso 1 1 calc R . . C17 C 0.4513(4) -0.0924(6) -0.3514(9) 0.0391(15) Uani 1 1 d . . . H17 H 0.4660 -0.0286 -0.3722 0.047 Uiso 1 1 calc R . . C18 C 0.3763(3) -0.1311(6) -0.4130(9) 0.0363(14) Uani 1 1 d . . . H18 H 0.3309 -0.0974 -0.4859 0.044 Uiso 1 1 calc R . . C19 C 0.4546(4) -0.2474(6) -0.2545(9) 0.0397(14) Uani 1 1 d . . . H19 H 0.4737 -0.3081 -0.1969 0.048 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 Co1 0.0210(4) 0.0366(5) 0.0392(4) -0.0038(4) 0.0056(3) 0.0006(4) N1 0.036(3) 0.044(3) 0.036(3) -0.001(2) 0.011(2) 0.002(3) N2 0.024(3) 0.049(4) 0.037(3) -0.001(3) 0.005(2) -0.005(2) N3 0.030(3) 0.031(3) 0.053(3) 0.000(2) 0.011(2) -0.002(2) N4 0.019(3) 0.040(3) 0.048(3) -0.007(2) 0.007(2) -0.002(2) O1 0.025(2) 0.067(4) 0.057(3) -0.010(3) 0.012(2) 0.000(2) O2 0.040(3) 0.044(3) 0.077(4) -0.001(3) 0.013(3) 0.012(2) O3 0.031(2) 0.043(3) 0.053(3) 0.005(2) 0.002(2) 0.006(2) O4 0.028(2) 0.055(3) 0.056(3) 0.001(2) -0.005(2) -0.009(2) Br1 0.0890(11) 0.0268(6) 0.1518(15) 0.000 0.0679(10) 0.000 Br2 0.0904(12) 0.0270(6) 0.1268(13) 0.000 0.0321(10) 0.000 C1 0.048(6) 0.026(5) 0.067(6) 0.000 0.032(5) 0.000 C2 0.027(3) 0.035(4) 0.056(4) -0.003(3) 0.017(3) -0.006(3) C3 0.030(3) 0.037(3) 0.038(3) -0.002(3) 0.011(2) -0.003(3) C4 0.031(4) 0.020(4) 0.041(4) 0.000 0.010(3) 0.000 C5 0.037(4) 0.047(4) 0.036(3) -0.004(3) 0.010(3) 0.004(3) C6 0.034(5) 0.027(5) 0.065(6) 0.000 0.013(4) 0.000 C7 0.037(4) 0.039(4) 0.046(4) -0.005(3) 0.008(3) -0.009(3) C8 0.031(3) 0.037(3) 0.034(3) 0.001(3) 0.009(2) -0.001(3) C9 0.028(4) 0.036(5) 0.034(4) 0.000 0.006(3) 0.000 C10 0.029(3) 0.043(4) 0.040(3) 0.001(3) 0.007(3) 0.001(3) C11 0.063(4) 0.040(4) 0.055(4) 0.004(4) 0.017(3) -0.018(4) C12 0.059(5) 0.053(5) 0.040(4) 0.004(3) 0.013(3) -0.017(4) C13 0.021(3) 0.040(4) 0.041(3) 0.001(3) 0.010(2) -0.002(2) C14 0.028(3) 0.055(5) 0.052(4) -0.013(3) 0.010(3) -0.011(3) C15 0.037(4) 0.049(5) 0.060(4) -0.004(4) 0.009(3) 0.005(3) C16 0.027(3) 0.050(4) 0.051(4) -0.006(3) 0.013(3) 0.001(3) C17 0.032(3) 0.037(4) 0.045(3) 0.011(3) 0.011(3) 0.004(3) C18 0.017(3) 0.049(4) 0.038(3) -0.003(3) 0.006(2) 0.005(3) C19 0.029(3) 0.032(3) 0.051(4) 0.002(3) 0.008(3) -0.001(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 Co1 O1 1.945(6) . ? Co1 O3 1.947(5) . ? Co1 N1 2.014(6) . ? Co1 N4 2.048(6) 3_556 ? N1 C13 1.336(10) . ? N1 C11 1.358(10) . ? N2 C13 1.336(9) . ? N2 C12 1.374(11) . ? N2 C14 1.467(10) . ? N3 C19 1.345(9) . ? N3 C17 1.377(9) . ? N3 C16 1.464(9) . ? N4 C19 1.330(8) . ? N4 C18 1.375(10) . ? N4 Co1 2.048(6) 3_444 ? O1 C5 1.304(10) . ? O2 C5 1.209(10) . ? O3 C10 1.285(9) . ? O4 C10 1.222(9) . ? Br1 C1 1.904(10) . ? Br2 C6 1.893(10) . ? C1 C2 1.369(8) 2_656 ? C1 C2 1.369(8) . ? C2 C3 1.405(10) . ? C2 H2 0.9300 . ? C3 C4 1.385(8) . ? C3 C5 1.508(10) . ? C4 C3 1.385(8) 2_656 ? C4 H4 0.9300 . ? C6 C7 1.388(9) 2_757 ? C6 C7 1.388(9) . ? C7 C8 1.380(10) . ? C7 H7 0.9300 . ? C8 C9 1.383(8) . ? C8 C10 1.498(9) . ? C9 C8 1.383(8) 2_757 ? C9 H9 0.9300 . ? C11 C12 1.346(12) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.539(10) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.512(11) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.380(9) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19 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 O1 Co1 O3 126.8(2) . . ? O1 Co1 N1 111.3(2) . . ? O3 Co1 N1 113.0(2) . . ? O1 Co1 N4 102.7(3) . 3_556 ? O3 Co1 N4 93.6(2) . 3_556 ? N1 Co1 N4 104.2(2) . 3_556 ? C13 N1 C11 106.0(6) . . ? C13 N1 Co1 125.7(5) . . ? C11 N1 Co1 128.3(6) . . ? C13 N2 C12 107.8(6) . . ? C13 N2 C14 124.3(6) . . ? C12 N2 C14 127.0(6) . . ? C19 N3 C17 108.1(6) . . ? C19 N3 C16 123.7(6) . . ? C17 N3 C16 127.9(6) . . ? C19 N4 C18 106.2(6) . . ? C19 N4 Co1 122.2(5) . 3_444 ? C18 N4 Co1 131.6(4) . 3_444 ? C5 O1 Co1 110.2(5) . . ? C10 O3 Co1 125.2(4) . . ? C2 C1 C2 122.7(9) 2_656 . ? C2 C1 Br1 118.6(5) 2_656 . ? C2 C1 Br1 118.6(5) . . ? C1 C2 C3 118.6(6) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 120.0(6) . . ? C4 C3 C5 119.4(6) . . ? C2 C3 C5 120.6(6) . . ? C3 C4 C3 120.1(8) . 2_656 ? C3 C4 H4 119.9 . . ? C3 C4 H4 119.9 2_656 . ? O2 C5 O1 122.8(7) . . ? O2 C5 C3 121.3(7) . . ? O1 C5 C3 116.0(6) . . ? C7 C6 C7 120.8(9) 2_757 . ? C7 C6 Br2 119.6(5) 2_757 . ? C7 C6 Br2 119.6(5) . . ? C8 C7 C6 119.6(7) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 119.2(7) . . ? C7 C8 C10 119.0(6) . . ? C9 C8 C10 121.8(7) . . ? C8 C9 C8 121.6(9) 2_757 . ? C8 C9 H9 119.2 2_757 . ? C8 C9 H9 119.2 . . ? O4 C10 O3 124.0(6) . . ? O4 C10 C8 120.9(7) . . ? O3 C10 C8 115.0(6) . . ? C12 C11 N1 110.1(8) . . ? C12 C11 H11 124.9 . . ? N1 C11 H11 124.9 . . ? C11 C12 N2 105.9(7) . . ? C11 C12 H12 127.1 . . ? N2 C12 H12 127.1 . . ? N2 C13 N1 110.2(6) . . ? N2 C13 H13 124.9 . . ? N1 C13 H13 124.9 . . ? N2 C14 C15 109.1(7) . . ? N2 C14 H14A 109.9 . . ? C15 C14 H14A 109.9 . . ? N2 C14 H14B 109.9 . . ? C15 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? C16 C15 C14 111.8(7) . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? N3 C16 C15 110.5(6) . . ? N3 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? N3 C17 C18 105.5(6) . . ? N3 C17 H17 127.3 . . ? C18 C17 H17 127.3 . . ? N4 C18 C17 109.3(6) . . ? N4 C18 H18 125.3 . . ? C17 C18 H18 125.3 . . ? N4 C19 N3 110.9(7) . . ? N4 C19 H19 124.6 . . ? N3 C19 H19 124.6 . . ? 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 O1 Co1 N1 C13 -112.2(6) . . . . ? O3 Co1 N1 C13 37.5(6) . . . . ? N4 Co1 N1 C13 137.7(6) 3_556 . . . ? O1 Co1 N1 C11 68.2(7) . . . . ? O3 Co1 N1 C11 -142.0(6) . . . . ? N4 Co1 N1 C11 -41.8(7) 3_556 . . . ? O3 Co1 O1 C5 -83.1(5) . . . . ? N1 Co1 O1 C5 61.4(5) . . . . ? N4 Co1 O1 C5 172.5(5) 3_556 . . . ? O1 Co1 O3 C10 103.7(6) . . . . ? N1 Co1 O3 C10 -40.4(7) . . . . ? N4 Co1 O3 C10 -147.5(6) 3_556 . . . ? C2 C1 C2 C3 0.2(5) 2_656 . . . ? Br1 C1 C2 C3 -179.8(5) . . . . ? C1 C2 C3 C4 -0.3(9) . . . . ? C1 C2 C3 C5 178.0(5) . . . . ? C2 C3 C4 C3 0.2(5) . . . 2_656 ? C5 C3 C4 C3 -178.2(7) . . . 2_656 ? Co1 O1 C5 O2 16.6(10) . . . . ? Co1 O1 C5 C3 -163.1(5) . . . . ? C4 C3 C5 O2 0.7(11) . . . . ? C2 C3 C5 O2 -177.6(7) . . . . ? C4 C3 C5 O1 -179.6(5) . . . . ? C2 C3 C5 O1 2.1(10) . . . . ? C7 C6 C7 C8 0.1(5) 2_757 . . . ? Br2 C6 C7 C8 -179.9(5) . . . . ? C6 C7 C8 C9 -0.2(10) . . . . ? C6 C7 C8 C10 178.2(5) . . . . ? C7 C8 C9 C8 0.1(5) . . . 2_757 ? C10 C8 C9 C8 -178.2(7) . . . 2_757 ? Co1 O3 C10 O4 -23.1(11) . . . . ? Co1 O3 C10 C8 158.0(4) . . . . ? C7 C8 C10 O4 1.7(10) . . . . ? C9 C8 C10 O4 180.0(6) . . . . ? C7 C8 C10 O3 -179.4(7) . . . . ? C9 C8 C10 O3 -1.1(9) . . . . ? C13 N1 C11 C12 1.7(9) . . . . ? Co1 N1 C11 C12 -178.8(6) . . . . ? N1 C11 C12 N2 -2.9(10) . . . . ? C13 N2 C12 C11 3.0(9) . . . . ? C14 N2 C12 C11 172.3(7) . . . . ? C12 N2 C13 N1 -2.1(8) . . . . ? C14 N2 C13 N1 -171.8(6) . . . . ? C11 N1 C13 N2 0.3(8) . . . . ? Co1 N1 C13 N2 -179.3(4) . . . . ? C13 N2 C14 C15 91.0(8) . . . . ? C12 N2 C14 C15 -76.7(9) . . . . ? N2 C14 C15 C16 -177.0(7) . . . . ? C19 N3 C16 C15 -138.0(8) . . . . ? C17 N3 C16 C15 48.5(10) . . . . ? C14 C15 C16 N3 -177.8(7) . . . . ? C19 N3 C17 C18 -0.8(8) . . . . ? C16 N3 C17 C18 173.5(7) . . . . ? C19 N4 C18 C17 -1.2(8) . . . . ? Co1 N4 C18 C17 -179.0(5) 3_444 . . . ? N3 C17 C18 N4 1.2(8) . . . . ? C18 N4 C19 N3 0.6(8) . . . . ? Co1 N4 C19 N3 178.7(5) 3_444 . . . ? C17 N3 C19 N4 0.1(8) . . . . ? C16 N3 C19 N4 -174.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.690 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.161 data_c _database_code_depnum_ccdc_archive 'CCDC 796640' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Br N4 Ni O5' _chemical_formula_weight 495.97 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' 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 9.7514(13) _cell_length_b 10.1430(14) _cell_length_c 11.2886(16) _cell_angle_alpha 108.3960(10) _cell_angle_beta 106.2630(10) _cell_angle_gamma 102.9210(10) _cell_volume 955.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2865 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 26.19 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.724 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 3.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5317 _exptl_absorpt_correction_T_max 0.8100 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7345 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3532 _reflns_number_gt 2966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.6929P] 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 3532 _refine_ls_number_parameters 253 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0650 _refine_ls_wR_factor_gt 0.0603 _refine_ls_goodness_of_fit_ref 1.025 _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 0.50219(4) 0.93746(3) -0.29642(3) 0.02300(10) Uani 1 1 d . . . N1 N 0.7039(3) 1.0548(2) -0.1294(2) 0.0293(5) Uani 1 1 d . . . N2 N 0.8739(3) 1.1342(2) 0.0769(2) 0.0316(5) Uani 1 1 d . . . N3 N 1.1341(3) 1.5931(3) 0.3725(2) 0.0387(6) Uani 1 1 d . . . N4 N 1.3011(3) 1.8012(2) 0.5370(2) 0.0313(5) Uani 1 1 d . . . O1 O 0.4706(2) 0.77672(19) -0.22659(19) 0.0308(4) Uani 1 1 d . . . O2 O 0.5863(3) 0.6372(2) -0.3283(2) 0.0413(5) Uani 1 1 d . . . O3 O 0.4888(2) 0.12710(19) -0.33762(18) 0.0286(4) Uani 1 1 d . . . O4 O 0.3917(2) 0.07222(19) -0.19845(19) 0.0307(4) Uani 1 1 d . . . O5 O 0.6295(2) 0.8651(2) -0.40680(18) 0.0312(4) Uani 1 1 d D . . H1W H 0.5870 0.8515 -0.4856 0.047 Uiso 1 1 d RD . . H2W H 0.6259 0.7861 -0.3983 0.047 Uiso 1 1 d RD . . C1 C 0.4415(3) 0.5462(3) -0.2151(3) 0.0241(6) Uani 1 1 d . . . C2 C 0.4579(3) 0.4087(3) -0.2580(3) 0.0243(6) Uani 1 1 d . . . H2 H 0.5097 0.3874 -0.3154 0.029 Uiso 1 1 calc R . . C3 C 0.3970(3) 0.3018(3) -0.2156(2) 0.0230(6) Uani 1 1 d . . . C4 C 0.3178(3) 0.3329(3) -0.1311(3) 0.0250(6) Uani 1 1 d . . . H4 H 0.2765 0.2626 -0.1025 0.030 Uiso 1 1 calc R . . C5 C 0.3015(3) 0.4702(3) -0.0904(3) 0.0253(6) Uani 1 1 d . . . C6 C 0.3631(3) 0.5769(3) -0.1304(3) 0.0266(6) Uani 1 1 d . . . H6 H 0.3520 0.6691 -0.1008 0.032 Uiso 1 1 calc R . . C7 C 0.5078(3) 0.6629(3) -0.2599(3) 0.0266(6) Uani 1 1 d . . . C8 C 0.4261(3) 0.1583(3) -0.2533(3) 0.0236(6) Uani 1 1 d . . . C9 C 0.8474(4) 1.1066(3) -0.1283(3) 0.0369(7) Uani 1 1 d . . . H9 H 0.8687 1.1087 -0.2032 0.044 Uiso 1 1 calc R . . C10 C 0.9527(4) 1.1540(3) -0.0031(3) 0.0385(7) Uani 1 1 d . . . H10 H 1.0576 1.1925 0.0236 0.046 Uiso 1 1 calc R . . C11 C 0.7252(3) 1.0738(3) -0.0038(3) 0.0316(7) Uani 1 1 d . . . H11 H 0.6471 1.0487 0.0257 0.038 Uiso 1 1 calc R . . C12 C 0.9390(4) 1.1716(3) 0.2226(3) 0.0422(8) Uani 1 1 d . . . H12A H 1.0318 1.1484 0.2435 0.051 Uiso 1 1 calc R . . H12B H 0.8680 1.1107 0.2457 0.051 Uiso 1 1 calc R . . C13 C 0.9744(4) 1.3345(4) 0.3092(3) 0.0470(8) Uani 1 1 d . . . H13A H 0.8800 1.3549 0.2965 0.056 Uiso 1 1 calc R . . H13B H 1.0217 1.3531 0.4035 0.056 Uiso 1 1 calc R . . C14 C 1.0771(4) 1.4366(3) 0.2756(3) 0.0445(8) Uani 1 1 d . . . H14A H 1.1632 1.4048 0.2727 0.053 Uiso 1 1 calc R . . H14B H 1.0228 1.4298 0.1863 0.053 Uiso 1 1 calc R . . C15 C 1.0678(4) 1.6994(4) 0.3774(3) 0.0497(9) Uani 1 1 d . . . H15 H 0.9707 1.6868 0.3225 0.060 Uiso 1 1 calc R . . C16 C 1.1726(4) 1.8269(3) 0.4786(3) 0.0428(8) Uani 1 1 d . . . H16 H 1.1589 1.9181 0.5043 0.051 Uiso 1 1 calc R . . C17 C 1.2729(4) 1.6590(3) 0.4697(3) 0.0353(7) Uani 1 1 d . . . H17 H 1.3415 1.6106 0.4879 0.042 Uiso 1 1 calc R . . Br1 Br 0.19094(4) 0.51523(3) 0.02190(3) 0.03922(10) 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 0.0340(2) 0.01374(17) 0.02232(18) 0.00801(13) 0.01104(15) 0.00852(14) N1 0.0373(14) 0.0215(12) 0.0263(13) 0.0081(10) 0.0121(11) 0.0076(10) N2 0.0372(14) 0.0231(12) 0.0261(12) 0.0069(10) 0.0089(11) 0.0040(11) N3 0.0457(16) 0.0242(13) 0.0282(13) 0.0046(10) 0.0030(12) 0.0021(12) N4 0.0384(14) 0.0232(12) 0.0263(12) 0.0071(10) 0.0095(11) 0.0077(11) O1 0.0474(12) 0.0187(9) 0.0342(11) 0.0152(8) 0.0198(10) 0.0138(9) O2 0.0622(15) 0.0356(12) 0.0558(14) 0.0312(11) 0.0402(13) 0.0287(11) O3 0.0464(12) 0.0207(9) 0.0275(10) 0.0125(8) 0.0190(9) 0.0167(9) O4 0.0475(12) 0.0187(9) 0.0349(11) 0.0156(8) 0.0208(10) 0.0138(9) O5 0.0441(12) 0.0256(10) 0.0268(10) 0.0114(8) 0.0163(9) 0.0125(9) C1 0.0289(14) 0.0188(13) 0.0247(14) 0.0106(11) 0.0074(12) 0.0095(11) C2 0.0340(15) 0.0193(13) 0.0237(14) 0.0098(11) 0.0130(12) 0.0124(12) C3 0.0291(15) 0.0152(12) 0.0226(13) 0.0079(11) 0.0067(12) 0.0073(11) C4 0.0271(15) 0.0205(13) 0.0294(14) 0.0131(11) 0.0108(12) 0.0071(11) C5 0.0244(14) 0.0249(14) 0.0262(14) 0.0084(11) 0.0101(12) 0.0097(12) C6 0.0314(15) 0.0192(13) 0.0294(15) 0.0086(11) 0.0099(12) 0.0128(12) C7 0.0348(16) 0.0200(14) 0.0235(14) 0.0110(11) 0.0073(12) 0.0085(12) C8 0.0318(15) 0.0152(12) 0.0223(13) 0.0083(11) 0.0077(12) 0.0077(11) C9 0.0476(19) 0.0283(15) 0.0328(17) 0.0096(13) 0.0208(15) 0.0065(14) C10 0.0356(17) 0.0326(17) 0.0395(18) 0.0069(14) 0.0168(15) 0.0056(14) C11 0.0360(17) 0.0236(14) 0.0291(16) 0.0078(12) 0.0120(13) 0.0041(13) C12 0.051(2) 0.0312(17) 0.0300(16) 0.0122(13) 0.0050(15) 0.0012(15) C13 0.055(2) 0.0421(19) 0.0269(17) 0.0069(14) 0.0109(15) 0.0020(16) C14 0.050(2) 0.0340(17) 0.0321(17) 0.0045(14) 0.0096(15) 0.0023(15) C15 0.046(2) 0.044(2) 0.0420(19) 0.0120(16) -0.0014(16) 0.0161(17) C16 0.049(2) 0.0287(16) 0.0394(18) 0.0097(14) 0.0038(16) 0.0144(15) C17 0.0417(18) 0.0248(15) 0.0304(16) 0.0076(13) 0.0064(14) 0.0095(14) Br1 0.03836(19) 0.04398(19) 0.0480(2) 0.02002(15) 0.02785(16) 0.02020(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 Ni1 O1 2.0240(18) . ? Ni1 N1 2.074(2) . ? Ni1 O5 2.0808(18) . ? Ni1 N4 2.091(2) 1_444 ? Ni1 O3 2.1394(17) 1_565 ? Ni1 O4 2.1503(19) 1_565 ? Ni1 C8 2.462(2) 1_565 ? N1 C11 1.317(3) . ? N1 C9 1.376(4) . ? N2 C11 1.349(4) . ? N2 C10 1.371(4) . ? N2 C12 1.472(4) . ? N3 C17 1.336(4) . ? N3 C15 1.370(4) . ? N3 C14 1.481(4) . ? N4 C17 1.322(3) . ? N4 C16 1.365(4) . ? N4 Ni1 2.091(2) 1_666 ? O1 C7 1.263(3) . ? O2 C7 1.243(3) . ? O3 C8 1.265(3) . ? O3 Ni1 2.1394(17) 1_545 ? O4 C8 1.259(3) . ? O4 Ni1 2.1503(19) 1_545 ? O5 H1W 0.8200 . ? O5 H2W 0.8311 . ? C1 C6 1.387(4) . ? C1 C2 1.386(3) . ? C1 C7 1.514(4) . ? C2 C3 1.398(3) . ? C2 H2 0.9300 . ? C3 C4 1.392(4) . ? C3 C8 1.498(3) . ? C4 C5 1.382(3) . ? C4 H4 0.9300 . ? C5 C6 1.381(4) . ? C5 Br1 1.897(3) . ? C6 H6 0.9300 . ? C8 Ni1 2.462(2) 1_545 ? C9 C10 1.349(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.530(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.489(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.359(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 O1 Ni1 N1 88.08(8) . . ? O1 Ni1 O5 98.28(7) . . ? N1 Ni1 O5 88.06(8) . . ? O1 Ni1 N4 87.12(8) . 1_444 ? N1 Ni1 N4 174.66(9) . 1_444 ? O5 Ni1 N4 90.33(8) . 1_444 ? O1 Ni1 O3 161.50(7) . 1_565 ? N1 Ni1 O3 93.88(8) . 1_565 ? O5 Ni1 O3 100.16(7) . 1_565 ? N4 Ni1 O3 91.41(8) 1_444 1_565 ? O1 Ni1 O4 100.07(7) . 1_565 ? N1 Ni1 O4 89.86(8) . 1_565 ? O5 Ni1 O4 161.45(7) . 1_565 ? N4 Ni1 O4 93.27(8) 1_444 1_565 ? O3 Ni1 O4 61.59(7) 1_565 1_565 ? O1 Ni1 C8 130.80(8) . 1_565 ? N1 Ni1 C8 90.62(9) . 1_565 ? O5 Ni1 C8 130.83(8) . 1_565 ? N4 Ni1 C8 94.29(9) 1_444 1_565 ? O3 Ni1 C8 30.92(7) 1_565 1_565 ? O4 Ni1 C8 30.73(7) 1_565 1_565 ? C11 N1 C9 105.0(2) . . ? C11 N1 Ni1 126.7(2) . . ? C9 N1 Ni1 127.42(19) . . ? C11 N2 C10 106.7(2) . . ? C11 N2 C12 126.6(3) . . ? C10 N2 C12 126.7(3) . . ? C17 N3 C15 106.8(2) . . ? C17 N3 C14 123.3(3) . . ? C15 N3 C14 129.7(3) . . ? C17 N4 C16 105.2(2) . . ? C17 N4 Ni1 122.7(2) . 1_666 ? C16 N4 Ni1 131.92(19) . 1_666 ? C7 O1 Ni1 126.16(17) . . ? C8 O3 Ni1 88.76(14) . 1_545 ? C8 O4 Ni1 88.45(15) . 1_545 ? Ni1 O5 H1W 109.5 . . ? Ni1 O5 H2W 100.0 . . ? H1W O5 H2W 111.9 . . ? C6 C1 C2 119.6(2) . . ? C6 C1 C7 119.7(2) . . ? C2 C1 C7 120.8(2) . . ? C1 C2 C3 120.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.8(2) . . ? C4 C3 C8 120.0(2) . . ? C2 C3 C8 120.0(2) . . ? C5 C4 C3 118.9(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C6 C5 C4 121.6(2) . . ? C6 C5 Br1 118.32(19) . . ? C4 C5 Br1 120.1(2) . . ? C5 C6 C1 119.7(2) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O2 C7 O1 126.5(2) . . ? O2 C7 C1 118.8(2) . . ? O1 C7 C1 114.6(2) . . ? O4 C8 O3 120.9(2) . . ? O4 C8 C3 119.8(2) . . ? O3 C8 C3 119.3(2) . . ? O4 C8 Ni1 60.82(13) . 1_545 ? O3 C8 Ni1 60.32(13) . 1_545 ? C3 C8 Ni1 173.73(19) . 1_545 ? C10 C9 N1 110.2(3) . . ? C10 C9 H9 124.9 . . ? N1 C9 H9 124.9 . . ? C9 C10 N2 106.2(3) . . ? C9 C10 H10 126.9 . . ? N2 C10 H10 126.9 . . ? N1 C11 N2 111.8(3) . . ? N1 C11 H11 124.1 . . ? N2 C11 H11 124.1 . . ? N2 C12 C13 113.1(3) . . ? N2 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? N2 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 112.7(3) . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? N3 C14 C13 113.7(3) . . ? N3 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? N3 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 N3 106.2(3) . . ? C16 C15 H15 126.9 . . ? N3 C15 H15 126.9 . . ? C15 C16 N4 109.8(3) . . ? C15 C16 H16 125.1 . . ? N4 C16 H16 125.1 . . ? N4 C17 N3 112.0(3) . . ? N4 C17 H17 124.0 . . ? N3 C17 H17 124.0 . . ? 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 O1 Ni1 N1 C11 -44.1(2) . . . . ? O5 Ni1 N1 C11 -142.5(2) . . . . ? N4 Ni1 N1 C11 -70.1(10) 1_444 . . . ? O3 Ni1 N1 C11 117.4(2) 1_565 . . . ? O4 Ni1 N1 C11 55.9(2) 1_565 . . . ? C8 Ni1 N1 C11 86.7(2) 1_565 . . . ? O1 Ni1 N1 C9 123.6(2) . . . . ? O5 Ni1 N1 C9 25.2(2) . . . . ? N4 Ni1 N1 C9 97.6(10) 1_444 . . . ? O3 Ni1 N1 C9 -74.9(2) 1_565 . . . ? O4 Ni1 N1 C9 -136.4(2) 1_565 . . . ? C8 Ni1 N1 C9 -105.6(2) 1_565 . . . ? N1 Ni1 O1 C7 -94.5(2) . . . . ? O5 Ni1 O1 C7 -6.8(2) . . . . ? N4 Ni1 O1 C7 83.1(2) 1_444 . . . ? O3 Ni1 O1 C7 169.0(2) 1_565 . . . ? O4 Ni1 O1 C7 176.0(2) 1_565 . . . ? C8 Ni1 O1 C7 176.3(2) 1_565 . . . ? C6 C1 C2 C3 -0.5(4) . . . . ? C7 C1 C2 C3 179.7(2) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C1 C2 C3 C8 -175.0(2) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C8 C3 C4 C5 175.6(2) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C3 C4 C5 Br1 178.76(19) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? Br1 C5 C6 C1 -178.5(2) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? C7 C1 C6 C5 179.5(2) . . . . ? Ni1 O1 C7 O2 9.3(4) . . . . ? Ni1 O1 C7 C1 -167.72(16) . . . . ? C6 C1 C7 O2 175.3(3) . . . . ? C2 C1 C7 O2 -4.9(4) . . . . ? C6 C1 C7 O1 -7.5(4) . . . . ? C2 C1 C7 O1 172.3(2) . . . . ? Ni1 O4 C8 O3 5.3(3) 1_545 . . . ? Ni1 O4 C8 C3 -172.8(2) 1_545 . . . ? Ni1 O3 C8 O4 -5.3(3) 1_545 . . . ? Ni1 O3 C8 C3 172.8(2) 1_545 . . . ? C4 C3 C8 O4 -6.8(4) . . . . ? C2 C3 C8 O4 169.0(2) . . . . ? C4 C3 C8 O3 175.1(2) . . . . ? C2 C3 C8 O3 -9.1(4) . . . . ? C4 C3 C8 Ni1 -100.6(17) . . . 1_545 ? C2 C3 C8 Ni1 75.2(17) . . . 1_545 ? C11 N1 C9 C10 0.8(3) . . . . ? Ni1 N1 C9 C10 -169.01(19) . . . . ? N1 C9 C10 N2 -1.0(3) . . . . ? C11 N2 C10 C9 0.9(3) . . . . ? C12 N2 C10 C9 -179.0(3) . . . . ? C9 N1 C11 N2 -0.3(3) . . . . ? Ni1 N1 C11 N2 169.66(17) . . . . ? C10 N2 C11 N1 -0.4(3) . . . . ? C12 N2 C11 N1 179.5(2) . . . . ? C11 N2 C12 C13 -97.1(3) . . . . ? C10 N2 C12 C13 82.8(4) . . . . ? N2 C12 C13 C14 -55.8(4) . . . . ? C17 N3 C14 C13 100.8(4) . . . . ? C15 N3 C14 C13 -84.5(4) . . . . ? C12 C13 C14 N3 -170.2(3) . . . . ? C17 N3 C15 C16 0.5(4) . . . . ? C14 N3 C15 C16 -174.8(3) . . . . ? N3 C15 C16 N4 -0.6(4) . . . . ? C17 N4 C16 C15 0.5(4) . . . . ? Ni1 N4 C16 C15 -175.6(2) 1_666 . . . ? C16 N4 C17 N3 -0.2(3) . . . . ? Ni1 N4 C17 N3 176.37(19) 1_666 . . . ? C15 N3 C17 N4 -0.2(4) . . . . ? C14 N3 C17 N4 175.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H1W O3 0.82 2.02 2.825(3) 165.5 2_664 O5 H2W O2 0.83 1.93 2.715(3) 157.8 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.597 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.064 # Attachment '- 2.cif' data_bb2 _database_code_depnum_ccdc_archive 'CCDC 796641' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 Br N4 Ni O4' _chemical_formula_weight 491.98 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' 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.1385(10) _cell_length_b 17.0608(17) _cell_length_c 21.875(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3783.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4019 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 26.04 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.727 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 3.171 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3564 _exptl_absorpt_correction_T_max 0.8576 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24201 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3524 _reflns_number_gt 2588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0211P)^2^+6.7177P] 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 3524 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.84985(3) 0.09538(3) 0.471803(18) 0.02252(11) Uani 1 1 d . . . O1 O 0.64285(19) 0.10254(14) 0.48345(9) 0.0281(5) Uani 1 1 d . . . O2 O 0.72474(19) 0.05819(15) 0.39704(10) 0.0297(6) Uani 1 1 d . . . O3 O 0.0301(2) 0.08452(14) 0.43220(10) 0.0294(6) Uani 1 1 d . . . O4 O 0.1499(2) 0.02309(13) 0.50361(10) 0.0270(5) Uani 1 1 d . . . N1 N 0.8993(3) 0.13594(17) 0.55768(13) 0.0305(7) Uani 1 1 d . . . N2 N 0.9782(3) 0.15286(19) 0.65028(13) 0.0365(8) Uani 1 1 d . . . N3 N 0.8481(3) 0.29132(17) 0.93590(13) 0.0314(7) Uani 1 1 d . . . N4 N 0.9243(3) 0.17966(18) 0.89971(13) 0.0366(7) Uani 1 1 d . . . Br1 Br 0.33302(4) 0.09056(4) 0.228140(17) 0.06637(19) Uani 1 1 d . . . C1 C 0.4923(3) 0.07694(19) 0.40235(14) 0.0225(7) Uani 1 1 d . . . C2 C 0.3819(3) 0.06892(19) 0.43909(15) 0.0238(7) Uani 1 1 d . . . H2 H 0.3916 0.0645 0.4812 0.029 Uiso 1 1 calc R . . C3 C 0.2561(3) 0.06749(19) 0.41333(14) 0.0220(7) Uani 1 1 d . . . C4 C 0.2416(3) 0.0758(2) 0.35048(15) 0.0301(8) Uani 1 1 d . . . H4 H 0.1581 0.0769 0.3329 0.036 Uiso 1 1 calc R . . C5 C 0.3530(3) 0.0823(2) 0.31449(14) 0.0323(8) Uani 1 1 d . . . C6 C 0.4779(3) 0.0823(2) 0.33913(15) 0.0287(8) Uani 1 1 d . . . H6 H 0.5516 0.0859 0.3140 0.034 Uiso 1 1 calc R . . C7 C 0.6284(3) 0.07879(19) 0.42918(14) 0.0236(7) Uani 1 1 d . . . C8 C 0.1357(3) 0.05703(19) 0.45358(15) 0.0228(7) Uani 1 1 d . . . C9 C 0.8543(4) 0.2054(2) 0.58080(18) 0.0446(10) Uani 1 1 d . . . H9 H 0.7987 0.2399 0.5603 0.053 Uiso 1 1 calc R . . C10 C 0.9023(4) 0.2166(3) 0.63760(18) 0.0498(11) Uani 1 1 d . . . H10 H 0.8866 0.2593 0.6630 0.060 Uiso 1 1 calc R . . C11 C 0.9740(3) 0.1060(2) 0.60087(15) 0.0317(8) Uani 1 1 d . . . H11 H 1.0184 0.0585 0.5977 0.038 Uiso 1 1 calc R . . C12 C 1.0613(4) 0.1424(3) 0.70416(17) 0.0513(11) Uani 1 1 d . . . H12A H 1.1221 0.1861 0.7069 0.062 Uiso 1 1 calc R . . H12B H 1.1131 0.0950 0.6991 0.062 Uiso 1 1 calc R . . C13 C 0.9849(4) 0.1367(3) 0.76339(16) 0.0484(11) Uani 1 1 d . . . H13A H 0.9341 0.0885 0.7640 0.058 Uiso 1 1 calc R . . H13B H 0.9241 0.1804 0.7666 0.058 Uiso 1 1 calc R . . C14 C 1.0804(4) 0.1378(3) 0.81717(17) 0.0500(11) Uani 1 1 d . . . H14A H 1.1496 0.0997 0.8096 0.060 Uiso 1 1 calc R . . H14B H 1.1214 0.1891 0.8193 0.060 Uiso 1 1 calc R . . C15 C 1.0177(5) 0.1199(2) 0.87848(18) 0.0525(12) Uani 1 1 d . . . H15A H 0.9719 0.0701 0.8756 0.063 Uiso 1 1 calc R . . H15B H 1.0869 0.1142 0.9087 0.063 Uiso 1 1 calc R . . C16 C 0.9517(4) 0.2544(2) 0.91402(16) 0.0365(9) Uani 1 1 d . . . H16 H 1.0342 0.2774 0.9090 0.044 Uiso 1 1 calc R . . C17 C 0.7489(4) 0.2365(2) 0.93556(19) 0.0456(10) Uani 1 1 d . . . H17 H 0.6627 0.2455 0.9482 0.055 Uiso 1 1 calc R . . C18 C 0.7951(4) 0.1676(2) 0.91415(19) 0.0467(11) Uani 1 1 d . . . H18 H 0.7482 0.1210 0.9101 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 Ni1 0.01248(18) 0.0358(2) 0.0193(2) 0.0020(2) -0.00081(16) 0.00056(19) O1 0.0174(10) 0.0476(15) 0.0194(12) -0.0009(11) -0.0023(9) 0.0012(11) O2 0.0142(11) 0.0555(16) 0.0194(12) 0.0003(11) 0.0011(9) 0.0036(11) O3 0.0134(10) 0.0411(15) 0.0337(13) 0.0078(12) 0.0024(9) 0.0027(10) O4 0.0213(11) 0.0356(14) 0.0241(12) 0.0049(11) -0.0002(10) -0.0006(10) N1 0.0280(15) 0.0376(18) 0.0258(16) -0.0019(14) -0.0021(13) -0.0034(14) N2 0.0384(17) 0.048(2) 0.0234(16) -0.0034(15) -0.0030(14) -0.0034(16) N3 0.0265(14) 0.0377(17) 0.0299(16) -0.0076(14) -0.0006(13) -0.0049(14) N4 0.0486(19) 0.0357(19) 0.0256(16) -0.0043(14) -0.0035(15) 0.0019(16) Br1 0.0349(2) 0.1448(5) 0.0194(2) 0.0063(3) -0.00529(16) 0.0066(3) C1 0.0167(15) 0.0276(19) 0.0232(17) -0.0007(15) -0.0011(13) 0.0003(13) C2 0.0190(15) 0.0319(19) 0.0204(17) 0.0005(14) 0.0003(13) -0.0011(14) C3 0.0135(14) 0.0302(18) 0.0222(17) 0.0009(15) 0.0003(13) 0.0010(14) C4 0.0145(15) 0.048(2) 0.0277(18) 0.0005(17) -0.0060(14) 0.0003(15) C5 0.0239(16) 0.057(3) 0.0158(16) 0.0004(16) -0.0018(14) -0.0004(18) C6 0.0174(15) 0.046(2) 0.0222(17) 0.0031(16) 0.0022(13) -0.0015(15) C7 0.0157(15) 0.036(2) 0.0195(17) 0.0045(14) 0.0003(12) -0.0033(14) C8 0.0149(15) 0.0228(17) 0.0307(19) -0.0033(14) 0.0007(14) -0.0017(14) C9 0.054(2) 0.044(2) 0.036(2) -0.0038(19) -0.0054(19) 0.014(2) C10 0.064(3) 0.044(3) 0.041(3) -0.014(2) 0.001(2) 0.005(2) C11 0.0310(17) 0.038(2) 0.0261(18) -0.0057(17) -0.0025(15) -0.0009(17) C12 0.043(2) 0.083(3) 0.028(2) -0.010(2) -0.0100(18) -0.001(2) C13 0.049(2) 0.065(3) 0.031(2) -0.002(2) -0.0053(19) -0.001(2) C14 0.058(3) 0.063(3) 0.029(2) -0.012(2) -0.007(2) 0.015(2) C15 0.083(3) 0.040(2) 0.034(2) -0.0046(19) -0.004(2) 0.020(2) C16 0.036(2) 0.040(2) 0.033(2) -0.0059(18) 0.0033(17) -0.0028(18) C17 0.034(2) 0.055(3) 0.048(2) -0.006(2) -0.0025(19) -0.012(2) C18 0.053(2) 0.041(3) 0.046(3) -0.004(2) -0.011(2) -0.017(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O3 2.030(2) 1_655 ? Ni1 N1 2.064(3) . ? Ni1 N3 2.086(3) 7_565 ? Ni1 O4 2.092(2) 5_656 ? Ni1 O1 2.118(2) . ? Ni1 O2 2.165(2) . ? Ni1 C7 2.447(3) . ? O1 C7 1.263(4) . ? O2 C7 1.253(4) . ? O3 C8 1.259(4) . ? O3 Ni1 2.030(2) 1_455 ? O4 C8 1.247(4) . ? O4 Ni1 2.092(2) 5_656 ? N1 C11 1.314(4) . ? N1 C9 1.367(5) . ? N2 C11 1.345(4) . ? N2 C10 1.361(5) . ? N2 C12 1.459(4) . ? N3 C16 1.315(4) . ? N3 C17 1.373(4) . ? N3 Ni1 2.086(3) 7_566 ? N4 C16 1.342(5) . ? N4 C18 1.363(5) . ? N4 C15 1.467(5) . ? Br1 C5 1.905(3) . ? C1 C2 1.385(4) . ? C1 C6 1.394(4) . ? C1 C7 1.500(4) . ? C2 C3 1.394(4) . ? C2 H2 0.9300 . ? C3 C4 1.390(4) . ? C3 C8 1.516(4) . ? C4 C5 1.380(4) . ? C4 H4 0.9300 . ? C5 C6 1.377(4) . ? C6 H6 0.9300 . ? C9 C10 1.348(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.512(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.524(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.515(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16 0.9300 . ? C17 C18 1.350(6) . ? C17 H17 0.9300 . ? C18 H18 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 O3 Ni1 N1 101.55(10) 1_655 . ? O3 Ni1 N3 86.09(10) 1_655 7_565 ? N1 Ni1 N3 91.95(12) . 7_565 ? O3 Ni1 O4 91.16(9) 1_655 5_656 ? N1 Ni1 O4 95.14(10) . 5_656 ? N3 Ni1 O4 172.78(10) 7_565 5_656 ? O3 Ni1 O1 161.50(9) 1_655 . ? N1 Ni1 O1 96.43(10) . . ? N3 Ni1 O1 89.04(10) 7_565 . ? O4 Ni1 O1 91.50(9) 5_656 . ? O3 Ni1 O2 100.26(8) 1_655 . ? N1 Ni1 O2 158.18(10) . . ? N3 Ni1 O2 88.98(10) 7_565 . ? O4 Ni1 O2 84.94(9) 5_656 . ? O1 Ni1 O2 61.78(8) . . ? O3 Ni1 C7 130.71(10) 1_655 . ? N1 Ni1 C7 127.48(11) . . ? N3 Ni1 C7 87.47(11) 7_565 . ? O4 Ni1 C7 89.28(10) 5_656 . ? O1 Ni1 C7 31.06(9) . . ? O2 Ni1 C7 30.77(9) . . ? C7 O1 Ni1 89.03(17) . . ? C7 O2 Ni1 87.16(18) . . ? C8 O3 Ni1 129.8(2) . 1_455 ? C8 O4 Ni1 132.4(2) . 5_656 ? C11 N1 C9 105.3(3) . . ? C11 N1 Ni1 131.6(2) . . ? C9 N1 Ni1 123.1(2) . . ? C11 N2 C10 107.1(3) . . ? C11 N2 C12 126.5(3) . . ? C10 N2 C12 126.1(3) . . ? C16 N3 C17 104.9(3) . . ? C16 N3 Ni1 125.0(2) . 7_566 ? C17 N3 Ni1 129.8(3) . 7_566 ? C16 N4 C18 106.8(3) . . ? C16 N4 C15 126.9(4) . . ? C18 N4 C15 126.0(4) . . ? C2 C1 C6 119.8(3) . . ? C2 C1 C7 121.3(3) . . ? C6 C1 C7 118.9(3) . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.6(3) . . ? C4 C3 C8 120.1(3) . . ? C2 C3 C8 120.3(3) . . ? C5 C4 C3 119.1(3) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C6 C5 C4 121.9(3) . . ? C6 C5 Br1 119.1(2) . . ? C4 C5 Br1 119.0(2) . . ? C5 C6 C1 119.0(3) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? O2 C7 O1 121.8(3) . . ? O2 C7 C1 119.4(3) . . ? O1 C7 C1 118.7(3) . . ? O2 C7 Ni1 62.07(16) . . ? O1 C7 Ni1 59.91(15) . . ? C1 C7 Ni1 174.5(2) . . ? O4 C8 O3 126.7(3) . . ? O4 C8 C3 118.1(3) . . ? O3 C8 C3 115.2(3) . . ? C10 C9 N1 110.1(4) . . ? C10 C9 H9 124.9 . . ? N1 C9 H9 124.9 . . ? C9 C10 N2 106.2(4) . . ? C9 C10 H10 126.9 . . ? N2 C10 H10 126.9 . . ? N1 C11 N2 111.4(3) . . ? N1 C11 H11 124.3 . . ? N2 C11 H11 124.3 . . ? N2 C12 C13 113.9(3) . . ? N2 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N2 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C12 C13 C14 109.6(3) . . ? C12 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? C12 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C13 114.5(4) . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14B 108.6 . . ? C13 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? N4 C15 C14 114.3(3) . . ? N4 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? N4 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? N3 C16 N4 112.0(3) . . ? N3 C16 H16 124.0 . . ? N4 C16 H16 124.0 . . ? C18 C17 N3 110.0(4) . . ? C18 C17 H17 125.0 . . ? N3 C17 H17 125.0 . . ? C17 C18 N4 106.4(4) . . ? C17 C18 H18 126.8 . . ? N4 C18 H18 126.8 . . ? 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 O3 Ni1 O1 C7 12.0(4) 1_655 . . . ? N1 Ni1 O1 C7 178.5(2) . . . . ? N3 Ni1 O1 C7 86.7(2) 7_565 . . . ? O4 Ni1 O1 C7 -86.11(19) 5_656 . . . ? O2 Ni1 O1 C7 -2.67(18) . . . . ? O3 Ni1 O2 C7 -172.61(19) 1_655 . . . ? N1 Ni1 O2 C7 5.9(4) . . . . ? N3 Ni1 O2 C7 -86.8(2) 7_565 . . . ? O4 Ni1 O2 C7 97.1(2) 5_656 . . . ? O1 Ni1 O2 C7 2.69(18) . . . . ? O3 Ni1 N1 C11 -58.7(3) 1_655 . . . ? N3 Ni1 N1 C11 -145.1(3) 7_565 . . . ? O4 Ni1 N1 C11 33.5(3) 5_656 . . . ? O1 Ni1 N1 C11 125.6(3) . . . . ? O2 Ni1 N1 C11 122.8(3) . . . . ? C7 Ni1 N1 C11 126.6(3) . . . . ? O3 Ni1 N1 C9 121.5(3) 1_655 . . . ? N3 Ni1 N1 C9 35.0(3) 7_565 . . . ? O4 Ni1 N1 C9 -146.3(3) 5_656 . . . ? O1 Ni1 N1 C9 -54.2(3) . . . . ? O2 Ni1 N1 C9 -57.1(4) . . . . ? C7 Ni1 N1 C9 -53.3(3) . . . . ? C6 C1 C2 C3 -1.1(5) . . . . ? C7 C1 C2 C3 179.9(3) . . . . ? C1 C2 C3 C4 -1.3(5) . . . . ? C1 C2 C3 C8 178.7(3) . . . . ? C2 C3 C4 C5 2.4(5) . . . . ? C8 C3 C4 C5 -177.6(3) . . . . ? C3 C4 C5 C6 -1.2(6) . . . . ? C3 C4 C5 Br1 178.2(3) . . . . ? C4 C5 C6 C1 -1.1(6) . . . . ? Br1 C5 C6 C1 179.5(3) . . . . ? C2 C1 C6 C5 2.3(5) . . . . ? C7 C1 C6 C5 -178.6(3) . . . . ? Ni1 O2 C7 O1 -4.7(3) . . . . ? Ni1 O2 C7 C1 174.0(3) . . . . ? Ni1 O1 C7 O2 4.8(3) . . . . ? Ni1 O1 C7 C1 -173.9(3) . . . . ? C2 C1 C7 O2 154.6(3) . . . . ? C6 C1 C7 O2 -24.5(5) . . . . ? C2 C1 C7 O1 -26.7(5) . . . . ? C6 C1 C7 O1 154.3(3) . . . . ? C2 C1 C7 Ni1 -101(2) . . . . ? C6 C1 C7 Ni1 80(2) . . . . ? O3 Ni1 C7 O2 9.6(2) 1_655 . . . ? N1 Ni1 C7 O2 -177.23(18) . . . . ? N3 Ni1 C7 O2 92.3(2) 7_565 . . . ? O4 Ni1 C7 O2 -81.30(19) 5_656 . . . ? O1 Ni1 C7 O2 -175.4(3) . . . . ? O3 Ni1 C7 O1 -174.99(17) 1_655 . . . ? N1 Ni1 C7 O1 -1.8(2) . . . . ? N3 Ni1 C7 O1 -92.4(2) 7_565 . . . ? O4 Ni1 C7 O1 94.10(19) 5_656 . . . ? O2 Ni1 C7 O1 175.4(3) . . . . ? O3 Ni1 C7 C1 -98(2) 1_655 . . . ? N1 Ni1 C7 C1 75(2) . . . . ? N3 Ni1 C7 C1 -15(2) 7_565 . . . ? O4 Ni1 C7 C1 171(2) 5_656 . . . ? O1 Ni1 C7 C1 77(2) . . . . ? O2 Ni1 C7 C1 -107(2) . . . . ? Ni1 O4 C8 O3 95.2(4) 5_656 . . . ? Ni1 O4 C8 C3 -85.0(3) 5_656 . . . ? Ni1 O3 C8 O4 7.0(5) 1_455 . . . ? Ni1 O3 C8 C3 -172.7(2) 1_455 . . . ? C4 C3 C8 O4 155.0(3) . . . . ? C2 C3 C8 O4 -25.0(5) . . . . ? C4 C3 C8 O3 -25.2(5) . . . . ? C2 C3 C8 O3 154.7(3) . . . . ? C11 N1 C9 C10 0.0(4) . . . . ? Ni1 N1 C9 C10 179.9(3) . . . . ? N1 C9 C10 N2 -0.2(5) . . . . ? C11 N2 C10 C9 0.4(4) . . . . ? C12 N2 C10 C9 173.4(4) . . . . ? C9 N1 C11 N2 0.2(4) . . . . ? Ni1 N1 C11 N2 -179.6(2) . . . . ? C10 N2 C11 N1 -0.4(4) . . . . ? C12 N2 C11 N1 -173.4(3) . . . . ? C11 N2 C12 C13 -122.3(4) . . . . ? C10 N2 C12 C13 65.9(6) . . . . ? N2 C12 C13 C14 -171.8(4) . . . . ? C12 C13 C14 C15 -171.1(4) . . . . ? C16 N4 C15 C14 -64.0(5) . . . . ? C18 N4 C15 C14 122.6(4) . . . . ? C13 C14 C15 N4 -66.8(5) . . . . ? C17 N3 C16 N4 0.1(4) . . . . ? Ni1 N3 C16 N4 173.7(2) 7_566 . . . ? C18 N4 C16 N3 -0.9(4) . . . . ? C15 N4 C16 N3 -175.3(3) . . . . ? C16 N3 C17 C18 0.7(4) . . . . ? Ni1 N3 C17 C18 -172.5(3) 7_566 . . . ? N3 C17 C18 N4 -1.2(5) . . . . ? C16 N4 C18 C17 1.2(4) . . . . ? C15 N4 C18 C17 175.7(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.970 _refine_diff_density_min -0.997 _refine_diff_density_rms 0.076