# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_9574 _database_code_depnum_ccdc_archive 'CCDC 824462' #TrackingRef '9574.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H52 Cl4 N12 Ni2 O2' _chemical_formula_weight 968.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1247(5) _cell_length_b 10.8254(6) _cell_length_c 11.4210(6) _cell_angle_alpha 64.4110(10) _cell_angle_beta 79.0580(10) _cell_angle_gamma 70.9430(10) _cell_volume 1065.38(10) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4412 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.39 _exptl_crystal_description BLOCK _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 1.185 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6118 _exptl_absorpt_correction_T_max 0.8907 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 13224 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4868 _reflns_number_gt 4292 _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^)+(0.0446P)^2^+0.4539P] 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 4868 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.99476(2) 0.69008(2) 0.44088(2) 0.01279(9) Uani 1 1 d . . . Cl1 Cl 0.83180(5) 0.53658(5) 0.49077(5) 0.01677(11) Uani 1 1 d . . . Cl2 Cl 1.16100(5) 0.81731(5) 0.39817(5) 0.01868(12) Uani 1 1 d . . . O1 O 0.68042(16) 1.19818(15) 0.17176(14) 0.0227(3) Uani 1 1 d . . . N1 N 0.99269(17) 0.73293(17) 0.24593(16) 0.0147(3) Uani 1 1 d . . . N2 N 0.87586(17) 0.83728(17) 0.19141(15) 0.0150(3) Uani 1 1 d . . . N3 N 0.81083(17) 0.88143(16) 0.38186(15) 0.0132(3) Uani 1 1 d . . . N4 N 0.92469(17) 0.70657(17) 0.61712(16) 0.0159(3) Uani 1 1 d . . . N5 N 0.79676(17) 0.80455(17) 0.61008(16) 0.0152(3) Uani 1 1 d . . . C1 C 1.0765(2) 0.7125(2) 0.14675(19) 0.0158(4) Uani 1 1 d . . . C2 C 1.0118(2) 0.8025(2) 0.02915(19) 0.0173(4) Uani 1 1 d . . . H2 H 1.0493 0.8082 -0.0553 0.021 Uiso 1 1 calc R . . C3 C 0.8835(2) 0.8811(2) 0.05982(18) 0.0158(4) Uani 1 1 d . . . C4 C 1.2175(2) 0.6091(2) 0.1671(2) 0.0208(4) Uani 1 1 d . . . H4A H 1.2886 0.6602 0.1461 0.031 Uiso 1 1 calc R . . H4B H 1.2345 0.5578 0.1105 0.031 Uiso 1 1 calc R . . H4C H 1.2226 0.5410 0.2581 0.031 Uiso 1 1 calc R . . C5 C 0.7681(2) 0.9929(2) -0.0233(2) 0.0204(4) Uani 1 1 d . . . H5A H 0.6882 0.9548 -0.0084 0.031 Uiso 1 1 calc R . . H5B H 0.8012 1.0213 -0.1150 0.031 Uiso 1 1 calc R . . H5C H 0.7394 1.0760 -0.0008 0.031 Uiso 1 1 calc R . . C6 C 0.7575(2) 0.8701(2) 0.27656(18) 0.0146(4) Uani 1 1 d . . . H6A H 0.7095 0.7937 0.3130 0.017 Uiso 1 1 calc R . . H6B H 0.6898 0.9610 0.2278 0.017 Uiso 1 1 calc R . . C7 C 0.8445(2) 1.0204(2) 0.33928(19) 0.0158(4) Uani 1 1 d . . . H7A H 0.8852 1.0193 0.4121 0.019 Uiso 1 1 calc R . . H7B H 0.9164 1.0290 0.2663 0.019 Uiso 1 1 calc R . . C8 C 0.7216(2) 1.1475(2) 0.2974(2) 0.0171(4) Uani 1 1 d . . . C9 C 0.6326(2) 1.2270(2) 0.3595(2) 0.0224(5) Uani 1 1 d . . . H9 H 0.6370 1.2156 0.4461 0.027 Uiso 1 1 calc R . . C10 C 0.5305(2) 1.3318(2) 0.2689(2) 0.0269(5) Uani 1 1 d . . . H10 H 0.4537 1.4030 0.2839 0.032 Uiso 1 1 calc R . . C11 C 0.5642(2) 1.3101(2) 0.1590(2) 0.0278(5) Uani 1 1 d . . . H11 H 0.5138 1.3652 0.0823 0.033 Uiso 1 1 calc R . . C12 C 0.7157(2) 0.8555(2) 0.49856(18) 0.0150(4) Uani 1 1 d . . . H12A H 0.6422 0.9447 0.4918 0.018 Uiso 1 1 calc R . . H12B H 0.6698 0.7835 0.5079 0.018 Uiso 1 1 calc R . . C13 C 0.9654(2) 0.6663(2) 0.7354(2) 0.0176(4) Uani 1 1 d . . . C14 C 0.8621(2) 0.7356(2) 0.8048(2) 0.0199(4) Uani 1 1 d . . . H14 H 0.8653 0.7239 0.8917 0.024 Uiso 1 1 calc R . . C15 C 0.7558(2) 0.8234(2) 0.72307(19) 0.0174(4) Uani 1 1 d . . . C16 C 1.1040(2) 0.5621(2) 0.7793(2) 0.0230(5) Uani 1 1 d . . . H16A H 1.0977 0.4650 0.8061 0.035 Uiso 1 1 calc R . . H16B H 1.1300 0.5712 0.8530 0.035 Uiso 1 1 calc R . . H16C H 1.1752 0.5817 0.7076 0.035 Uiso 1 1 calc R . . C17 C 0.6225(2) 0.9275(2) 0.7401(2) 0.0209(4) Uani 1 1 d . . . H17A H 0.6347 1.0238 0.6992 0.031 Uiso 1 1 calc R . . H17B H 0.5975 0.9032 0.8330 0.031 Uiso 1 1 calc R . . H17C H 0.5478 0.9240 0.6992 0.031 Uiso 1 1 calc R . . C1S C 0.5404(3) 0.6902(3) 0.2030(3) 0.0303(5) Uani 1 1 d . . . C2S C 0.5103(3) 0.6247(3) 0.3422(2) 0.0293(5) Uani 1 1 d . . . H2S1 H 0.4133 0.6195 0.3591 0.044 Uiso 1 1 calc R . . H2S2 H 0.5236 0.6819 0.3837 0.044 Uiso 1 1 calc R . . H2S3 H 0.5737 0.5284 0.3777 0.044 Uiso 1 1 calc R . . N1S N 0.5639(3) 0.7412(3) 0.0938(2) 0.0492(6) 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 0.01142(14) 0.01235(13) 0.01167(14) -0.00329(10) -0.00185(9) -0.00101(10) Cl1 0.0137(2) 0.0132(2) 0.0193(2) -0.00356(18) -0.00376(18) -0.00118(17) Cl2 0.0146(2) 0.0190(2) 0.0212(3) -0.0061(2) -0.00217(19) -0.00513(18) O1 0.0208(8) 0.0208(7) 0.0195(7) -0.0048(6) -0.0033(6) -0.0001(6) N1 0.0118(8) 0.0136(8) 0.0155(8) -0.0042(6) -0.0031(6) -0.0004(6) N2 0.0130(8) 0.0175(8) 0.0116(8) -0.0043(7) -0.0019(6) -0.0017(6) N3 0.0124(8) 0.0126(7) 0.0125(8) -0.0039(6) 0.0001(6) -0.0026(6) N4 0.0130(8) 0.0156(8) 0.0158(8) -0.0047(7) -0.0017(6) -0.0015(6) N5 0.0130(8) 0.0164(8) 0.0148(8) -0.0064(7) -0.0012(6) -0.0018(6) C1 0.0159(10) 0.0155(9) 0.0158(9) -0.0056(8) 0.0007(8) -0.0058(8) C2 0.0185(10) 0.0200(10) 0.0135(9) -0.0061(8) 0.0000(8) -0.0067(8) C3 0.0193(10) 0.0158(9) 0.0130(9) -0.0046(8) -0.0021(8) -0.0068(8) C4 0.0180(11) 0.0231(10) 0.0183(10) -0.0080(9) 0.0003(8) -0.0027(8) C5 0.0219(11) 0.0219(10) 0.0142(10) -0.0046(8) -0.0050(8) -0.0035(8) C6 0.0117(9) 0.0163(9) 0.0135(9) -0.0051(7) -0.0019(7) -0.0016(7) C7 0.0130(9) 0.0155(9) 0.0171(10) -0.0055(8) -0.0016(8) -0.0026(7) C8 0.0161(10) 0.0148(9) 0.0188(10) -0.0040(8) -0.0037(8) -0.0043(8) C9 0.0227(11) 0.0173(10) 0.0284(12) -0.0112(9) -0.0053(9) -0.0022(8) C10 0.0199(11) 0.0156(10) 0.0431(14) -0.0118(10) -0.0071(10) 0.0010(8) C11 0.0238(12) 0.0169(10) 0.0328(13) -0.0018(9) -0.0104(10) 0.0004(9) C12 0.0132(9) 0.0172(9) 0.0126(9) -0.0059(8) -0.0005(7) -0.0017(7) C13 0.0188(10) 0.0176(9) 0.0165(10) -0.0042(8) -0.0050(8) -0.0066(8) C14 0.0225(11) 0.0236(10) 0.0154(10) -0.0078(8) -0.0016(8) -0.0081(9) C15 0.0195(10) 0.0201(10) 0.0157(9) -0.0084(8) 0.0010(8) -0.0086(8) C16 0.0232(11) 0.0236(11) 0.0198(10) -0.0061(9) -0.0072(9) -0.0036(9) C17 0.0202(11) 0.0242(11) 0.0201(10) -0.0123(9) 0.0021(8) -0.0053(9) C1S 0.0220(12) 0.0293(12) 0.0388(15) -0.0112(11) -0.0061(10) -0.0068(10) C2S 0.0235(12) 0.0346(13) 0.0340(13) -0.0175(11) -0.0016(10) -0.0082(10) N1S 0.0458(15) 0.0532(15) 0.0372(14) -0.0007(12) -0.0063(11) -0.0211(12) _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 N4 2.0670(17) . ? Ni1 N1 2.0718(16) . ? Ni1 N3 2.2282(16) . ? Ni1 Cl2 2.3642(5) . ? Ni1 Cl1 2.4011(5) 2_766 ? Ni1 Cl1 2.5345(5) . ? Cl1 Ni1 2.4011(5) 2_766 ? O1 C11 1.362(3) . ? O1 C8 1.390(2) . ? N1 C1 1.334(3) . ? N1 N2 1.365(2) . ? N2 C3 1.362(2) . ? N2 C6 1.444(2) . ? N3 C12 1.466(2) . ? N3 C6 1.473(2) . ? N3 C7 1.502(2) . ? N4 C13 1.331(3) . ? N4 N5 1.370(2) . ? N5 C15 1.359(3) . ? N5 C12 1.448(2) . ? C1 C2 1.403(3) . ? C1 C4 1.485(3) . ? C2 C3 1.377(3) . ? C3 C5 1.495(3) . ? C7 C8 1.486(3) . ? C8 C9 1.355(3) . ? C9 C10 1.433(3) . ? C10 C11 1.336(3) . ? C13 C14 1.404(3) . ? C13 C16 1.496(3) . ? C14 C15 1.371(3) . ? C15 C17 1.492(3) . ? C1S N1S 1.138(3) . ? C1S C2S 1.451(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ni1 N1 157.95(6) . . ? N4 Ni1 N3 79.06(6) . . ? N1 Ni1 N3 79.17(6) . . ? N4 Ni1 Cl2 93.31(5) . . ? N1 Ni1 Cl2 92.30(5) . . ? N3 Ni1 Cl2 95.79(4) . . ? N4 Ni1 Cl1 101.02(5) . 2_766 ? N1 Ni1 Cl1 99.95(5) . 2_766 ? N3 Ni1 Cl1 171.21(4) . 2_766 ? Cl2 Ni1 Cl1 92.980(19) . 2_766 ? N4 Ni1 Cl1 87.79(5) . . ? N1 Ni1 Cl1 88.21(5) . . ? N3 Ni1 Cl1 88.54(4) . . ? Cl2 Ni1 Cl1 175.656(18) . . ? Cl1 Ni1 Cl1 82.683(19) 2_766 . ? Ni1 Cl1 Ni1 97.319(19) 2_766 . ? C11 O1 C8 106.43(17) . . ? C1 N1 N2 105.57(15) . . ? C1 N1 Ni1 141.49(14) . . ? N2 N1 Ni1 111.57(12) . . ? C3 N2 N1 111.88(16) . . ? C3 N2 C6 129.03(16) . . ? N1 N2 C6 118.35(15) . . ? C12 N3 C6 111.78(15) . . ? C12 N3 C7 111.42(15) . . ? C6 N3 C7 112.50(15) . . ? C12 N3 Ni1 103.44(11) . . ? C6 N3 Ni1 102.75(11) . . ? C7 N3 Ni1 114.35(12) . . ? C13 N4 N5 105.34(16) . . ? C13 N4 Ni1 142.26(14) . . ? N5 N4 Ni1 111.91(12) . . ? C15 N5 N4 111.84(16) . . ? C15 N5 C12 128.54(17) . . ? N4 N5 C12 118.82(15) . . ? N1 C1 C2 110.12(17) . . ? N1 C1 C4 121.61(17) . . ? C2 C1 C4 128.26(18) . . ? C3 C2 C1 106.69(18) . . ? N2 C3 C2 105.73(17) . . ? N2 C3 C5 122.64(18) . . ? C2 C3 C5 131.63(18) . . ? N2 C6 N3 107.60(15) . . ? C8 C7 N3 113.88(16) . . ? C9 C8 O1 109.37(17) . . ? C9 C8 C7 132.88(19) . . ? O1 C8 C7 117.70(17) . . ? C8 C9 C10 106.4(2) . . ? C11 C10 C9 106.9(2) . . ? C10 C11 O1 110.87(19) . . ? N5 C12 N3 108.18(15) . . ? N4 C13 C14 110.18(18) . . ? N4 C13 C16 121.57(19) . . ? C14 C13 C16 128.25(19) . . ? C15 C14 C13 106.83(18) . . ? N5 C15 C14 105.79(18) . . ? N5 C15 C17 122.75(18) . . ? C14 C15 C17 131.39(19) . . ? N1S C1S C2S 179.7(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.605 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.080 data_9610 _database_code_depnum_ccdc_archive 'CCDC 824463' #TrackingRef '9610.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H52 Cl4 N12 Ni2 S2' _chemical_formula_weight 1000.26 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' S S 0.1246 0.1234 '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' Ni Ni 0.3393 1.1124 '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 10.5138(5) _cell_length_b 10.8388(5) _cell_length_c 11.9790(6) _cell_angle_alpha 111.1920(10) _cell_angle_beta 101.9870(10) _cell_angle_gamma 108.7390(10) _cell_volume 1121.32(9) _cell_formula_units_Z 1 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6583 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 1.215 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6689 _exptl_absorpt_correction_T_max 0.8679 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 14658 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5146 _reflns_number_gt 4592 _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^)+(0.0470P)^2^+0.4698P] 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 5146 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.002 _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 0.92702(2) 0.59637(3) 0.11160(2) 0.02202(8) Uani 1 1 d . . . S1 S 1.03463(7) 0.92795(6) 0.62716(5) 0.03692(14) Uani 1 1 d . . . Cl1 Cl 0.77638(6) 0.71754(6) 0.10032(5) 0.03427(13) Uani 1 1 d . . . Cl2 Cl 1.08924(5) 0.46674(5) 0.10478(4) 0.02748(12) Uani 1 1 d . . . N1 N 0.76375(18) 0.40932(18) 0.08768(15) 0.0270(3) Uani 1 1 d . . . N2 N 0.78473(18) 0.38861(18) 0.19460(16) 0.0273(3) Uani 1 1 d . . . N3 N 0.96613(17) 0.63305(17) 0.31375(15) 0.0231(3) Uani 1 1 d . . . N4 N 1.11039(18) 0.79334(18) 0.20912(15) 0.0250(3) Uani 1 1 d . . . N5 N 1.16807(17) 0.83211(18) 0.33672(15) 0.0262(3) Uani 1 1 d . . . N1S N 0.5822(3) 0.3776(3) 0.5608(3) 0.0668(7) Uani 1 1 d . . . C1 C 0.6348(2) 0.3010(2) 0.0024(2) 0.0307(4) Uani 1 1 d . . . C2 C 0.5765(2) 0.2108(2) 0.0554(2) 0.0361(5) Uani 1 1 d . . . H2 H 0.4874 0.1270 0.0151 0.043 Uiso 1 1 calc R . . C3 C 0.6732(2) 0.2673(2) 0.1766(2) 0.0322(4) Uani 1 1 d . . . C4 C 0.5729(3) 0.2881(3) -0.1266(2) 0.0441(6) Uani 1 1 d . . . H4A H 0.6269 0.3782 -0.1283 0.066 Uiso 1 1 calc R . . H4B H 0.4727 0.2710 -0.1448 0.066 Uiso 1 1 calc R . . H4C H 0.5786 0.2065 -0.1911 0.066 Uiso 1 1 calc R . . C5 C 0.6699(3) 0.2158(3) 0.2765(2) 0.0442(6) Uani 1 1 d . . . H5A H 0.7568 0.2034 0.3030 0.066 Uiso 1 1 calc R . . H5B H 0.5860 0.1226 0.2410 0.066 Uiso 1 1 calc R . . H5C H 0.6650 0.2878 0.3504 0.066 Uiso 1 1 calc R . . C6 C 0.9208(2) 0.4854(2) 0.30316(18) 0.0269(4) Uani 1 1 d . . . H6A H 0.9942 0.4504 0.2897 0.032 Uiso 1 1 calc R . . H6B H 0.9086 0.4869 0.3825 0.032 Uiso 1 1 calc R . . C7 C 0.8832(2) 0.7096(2) 0.37223(18) 0.0264(4) Uani 1 1 d . . . H7A H 0.7799 0.6452 0.3241 0.032 Uiso 1 1 calc R . . H7B H 0.9043 0.7984 0.3611 0.032 Uiso 1 1 calc R . . C8 C 0.9128(2) 0.7528(2) 0.51201(19) 0.0272(4) Uani 1 1 d . . . C9 C 0.8477(3) 0.6667(3) 0.5674(2) 0.0357(5) Uani 1 1 d . . . H9 H 0.7748 0.5698 0.5217 0.043 Uiso 1 1 calc R . . C10 C 0.9124(3) 0.7533(3) 0.7068(2) 0.0403(5) Uani 1 1 d . . . H10 H 0.8874 0.7156 0.7626 0.048 Uiso 1 1 calc R . . C11 C 1.0105(3) 0.8911(3) 0.7492(2) 0.0383(5) Uani 1 1 d . . . H11 H 1.0602 0.9595 0.8367 0.046 Uiso 1 1 calc R . . C12 C 1.1232(2) 0.7199(2) 0.37803(18) 0.0249(4) Uani 1 1 d . . . H12A H 1.1495 0.7659 0.4716 0.030 Uiso 1 1 calc R . . H12B H 1.1717 0.6561 0.3554 0.030 Uiso 1 1 calc R . . C13 C 1.1821(2) 0.9102(2) 0.19616(19) 0.0274(4) Uani 1 1 d . . . C14 C 1.2885(2) 1.0221(2) 0.3157(2) 0.0332(5) Uani 1 1 d . . . H14 H 1.3546 1.1149 0.3323 0.040 Uiso 1 1 calc R . . C15 C 1.2772(2) 0.9698(2) 0.4031(2) 0.0305(4) Uani 1 1 d . . . C16 C 1.1468(3) 0.9121(2) 0.0699(2) 0.0358(5) Uani 1 1 d . . . H16A H 1.1979 0.8689 0.0215 0.054 Uiso 1 1 calc R . . H16B H 1.1757 1.0127 0.0843 0.054 Uiso 1 1 calc R . . H16C H 1.0436 0.8559 0.0219 0.054 Uiso 1 1 calc R . . C17 C 1.3609(3) 1.0393(3) 0.5443(2) 0.0438(6) Uani 1 1 d . . . H17A H 1.2981 1.0549 0.5914 0.066 Uiso 1 1 calc R . . H17B H 1.4403 1.1328 0.5704 0.066 Uiso 1 1 calc R . . H17C H 1.3986 0.9751 0.5626 0.066 Uiso 1 1 calc R . . C1S C 0.5751(3) 0.4604(3) 0.6466(3) 0.0480(6) Uani 1 1 d . . . C2S C 0.5686(4) 0.5675(4) 0.7571(3) 0.0662(9) Uani 1 1 d . . . H2S1 H 0.6493 0.5985 0.8333 0.099 Uiso 1 1 calc R . . H2S2 H 0.4788 0.5242 0.7681 0.099 Uiso 1 1 calc R . . H2S3 H 0.5732 0.6519 0.7441 0.099 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 0.02488(14) 0.02320(14) 0.01572(13) 0.00694(10) 0.00699(10) 0.01050(10) S1 0.0480(3) 0.0337(3) 0.0281(3) 0.0111(2) 0.0175(2) 0.0181(3) Cl1 0.0356(3) 0.0390(3) 0.0275(3) 0.0107(2) 0.0083(2) 0.0229(2) Cl2 0.0350(3) 0.0329(3) 0.0186(2) 0.01120(19) 0.01130(19) 0.0193(2) N1 0.0299(9) 0.0280(8) 0.0194(8) 0.0088(7) 0.0086(7) 0.0111(7) N2 0.0323(9) 0.0269(8) 0.0222(8) 0.0112(7) 0.0107(7) 0.0122(7) N3 0.0266(8) 0.0247(8) 0.0183(8) 0.0084(6) 0.0087(6) 0.0129(7) N4 0.0277(8) 0.0282(8) 0.0175(8) 0.0090(7) 0.0072(6) 0.0128(7) N5 0.0252(8) 0.0293(9) 0.0167(8) 0.0079(7) 0.0041(6) 0.0087(7) N1S 0.0668(17) 0.0555(15) 0.0595(16) 0.0175(13) 0.0275(14) 0.0130(13) C1 0.0270(10) 0.0308(10) 0.0265(10) 0.0069(8) 0.0095(8) 0.0110(8) C2 0.0332(11) 0.0284(11) 0.0342(12) 0.0073(9) 0.0142(9) 0.0059(9) C3 0.0381(11) 0.0268(10) 0.0365(12) 0.0146(9) 0.0214(10) 0.0148(9) C4 0.0342(12) 0.0504(14) 0.0285(11) 0.0113(11) 0.0042(10) 0.0088(11) C5 0.0539(15) 0.0390(13) 0.0474(14) 0.0260(11) 0.0263(12) 0.0173(11) C6 0.0336(11) 0.0283(10) 0.0217(9) 0.0125(8) 0.0113(8) 0.0150(9) C7 0.0307(10) 0.0280(10) 0.0235(9) 0.0109(8) 0.0121(8) 0.0160(8) C8 0.0326(10) 0.0258(10) 0.0254(10) 0.0102(8) 0.0142(8) 0.0149(8) C9 0.0638(15) 0.0391(12) 0.0283(11) 0.0200(9) 0.0310(11) 0.0361(12) C10 0.0664(16) 0.0452(13) 0.0350(12) 0.0257(11) 0.0323(12) 0.0371(13) C11 0.0550(14) 0.0457(13) 0.0249(11) 0.0158(10) 0.0186(10) 0.0322(12) C12 0.0285(10) 0.0288(10) 0.0169(9) 0.0099(8) 0.0070(7) 0.0135(8) C13 0.0293(10) 0.0277(10) 0.0271(10) 0.0121(8) 0.0128(8) 0.0137(8) C14 0.0286(10) 0.0308(11) 0.0324(11) 0.0122(9) 0.0105(9) 0.0072(9) C15 0.0225(10) 0.0320(11) 0.0248(10) 0.0069(8) 0.0061(8) 0.0064(8) C16 0.0454(13) 0.0344(11) 0.0287(11) 0.0160(9) 0.0157(10) 0.0158(10) C17 0.0326(12) 0.0444(13) 0.0251(11) 0.0073(10) 0.0019(9) -0.0015(10) C1S 0.0426(14) 0.0456(14) 0.0491(16) 0.0211(13) 0.0130(12) 0.0146(12) C2S 0.067(2) 0.070(2) 0.0582(19) 0.0174(16) 0.0172(16) 0.0428(17) _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 N4 2.0630(17) . ? Ni1 N1 2.0685(17) . ? Ni1 N3 2.2308(15) . ? Ni1 Cl1 2.3722(5) . ? Ni1 Cl2 2.3822(5) 2_765 ? Ni1 Cl2 2.5306(5) . ? S1 C11 1.695(2) . ? S1 C8 1.720(2) . ? Cl2 Ni1 2.3821(5) 2_765 ? N1 C1 1.340(3) . ? N1 N2 1.364(2) . ? N2 C3 1.360(3) . ? N2 C6 1.454(3) . ? N3 C6 1.464(2) . ? N3 C12 1.468(2) . ? N3 C7 1.496(2) . ? N4 C13 1.332(3) . ? N4 N5 1.366(2) . ? N5 C15 1.356(3) . ? N5 C12 1.453(2) . ? N1S C1S 1.129(4) . ? C1 C2 1.400(3) . ? C1 C4 1.483(3) . ? C2 C3 1.364(3) . ? C3 C5 1.495(3) . ? C7 C8 1.498(3) . ? C8 C9 1.416(3) . ? C9 C10 1.455(3) . ? C10 C11 1.340(4) . ? C13 C14 1.407(3) . ? C13 C16 1.490(3) . ? C14 C15 1.367(3) . ? C15 C17 1.495(3) . ? C1S C2S 1.444(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ni1 N1 157.09(6) . . ? N4 Ni1 N3 79.53(6) . . ? N1 Ni1 N3 77.67(6) . . ? N4 Ni1 Cl1 91.71(5) . . ? N1 Ni1 Cl1 93.72(5) . . ? N3 Ni1 Cl1 98.14(4) . . ? N4 Ni1 Cl2 100.65(5) . 2_765 ? N1 Ni1 Cl2 101.36(5) . 2_765 ? N3 Ni1 Cl2 169.68(4) . 2_765 ? Cl1 Ni1 Cl2 92.166(19) . 2_765 ? N4 Ni1 Cl2 88.15(5) . . ? N1 Ni1 Cl2 88.39(5) . . ? N3 Ni1 Cl2 86.92(4) . . ? Cl1 Ni1 Cl2 174.828(18) . . ? Cl2 Ni1 Cl2 82.782(17) 2_765 . ? C11 S1 C8 92.59(11) . . ? Ni1 Cl2 Ni1 97.218(17) 2_765 . ? C1 N1 N2 105.56(16) . . ? C1 N1 Ni1 141.03(14) . . ? N2 N1 Ni1 113.26(12) . . ? C3 N2 N1 111.56(17) . . ? C3 N2 C6 129.47(17) . . ? N1 N2 C6 118.74(16) . . ? C6 N3 C12 111.56(15) . . ? C6 N3 C7 112.36(15) . . ? C12 N3 C7 113.24(15) . . ? C6 N3 Ni1 104.23(11) . . ? C12 N3 Ni1 103.27(11) . . ? C7 N3 Ni1 111.46(11) . . ? C13 N4 N5 105.70(16) . . ? C13 N4 Ni1 141.11(14) . . ? N5 N4 Ni1 112.08(12) . . ? C15 N5 N4 111.64(16) . . ? C15 N5 C12 129.22(16) . . ? N4 N5 C12 118.40(15) . . ? N1 C1 C2 109.64(19) . . ? N1 C1 C4 121.51(19) . . ? C2 C1 C4 128.8(2) . . ? C3 C2 C1 107.14(19) . . ? N2 C3 C2 106.07(18) . . ? N2 C3 C5 123.0(2) . . ? C2 C3 C5 130.9(2) . . ? N2 C6 N3 108.14(15) . . ? N3 C7 C8 115.78(16) . . ? C9 C8 C7 127.99(19) . . ? C9 C8 S1 111.73(16) . . ? C7 C8 S1 120.24(15) . . ? C8 C9 C10 108.7(2) . . ? C11 C10 C9 114.6(2) . . ? C10 C11 S1 112.35(18) . . ? N5 C12 N3 108.56(15) . . ? N4 C13 C14 109.72(18) . . ? N4 C13 C16 121.80(18) . . ? C14 C13 C16 128.47(19) . . ? C15 C14 C13 106.79(19) . . ? N5 C15 C14 106.12(18) . . ? N5 C15 C17 122.92(19) . . ? C14 C15 C17 131.0(2) . . ? N1S C1S C2S 179.1(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.666 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.073 data_a277 _database_code_depnum_ccdc_archive 'CCDC 824464' #TrackingRef 'A277.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H54 Cl8 N10 Ni2 S2' _chemical_formula_weight 1116.05 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' S S 0.1246 0.1234 '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' 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 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 11.1367(16) _cell_length_b 14.948(2) _cell_length_c 14.731(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.788(4) _cell_angle_gamma 90.00 _cell_volume 2439.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 776 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 24.42 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.336 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7061 _exptl_absorpt_correction_T_max 0.8562 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 '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 17146 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5592 _reflns_number_gt 4300 _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^)+(0.0538P)^2^+2.6088P] 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 5592 _refine_ls_number_parameters 321 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.056 _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 Ni1 Ni 0.52460(4) 0.50804(3) 0.38132(3) 0.01434(13) Uani 1 1 d . . . Cl1 Cl 0.54432(8) 0.39660(5) 0.26777(5) 0.0202(2) Uani 1 1 d . . . Cl2 Cl 0.49626(8) 0.60837(5) 0.50994(5) 0.01877(19) Uani 1 1 d . . . N1 N 0.3469(2) 0.53180(18) 0.33135(19) 0.0162(6) Uani 1 1 d . . . N2 N 0.3342(3) 0.61151(18) 0.28555(19) 0.0183(6) Uani 1 1 d . . . N3 N 0.5464(2) 0.62860(18) 0.29479(18) 0.0155(6) Uani 1 1 d . . . N4 N 0.7083(3) 0.52941(18) 0.40188(19) 0.0167(6) Uani 1 1 d . . . N5 N 0.7411(3) 0.61105(18) 0.37089(19) 0.0185(6) Uani 1 1 d . . . C1 C 0.2398(3) 0.4918(2) 0.3169(2) 0.0190(7) Uani 1 1 d . . . C2 C 0.1590(3) 0.5465(2) 0.2628(2) 0.0223(8) Uani 1 1 d . . . H2 H 0.0788 0.5338 0.2435 0.027 Uiso 1 1 calc R . . C3 C 0.2214(3) 0.6226(2) 0.2440(2) 0.0215(8) Uani 1 1 d . . . C4 C 0.2192(3) 0.4003(2) 0.3535(3) 0.0237(8) Uani 1 1 d . . . H4A H 0.2945 0.3761 0.3802 0.036 Uiso 1 1 calc R . . H4B H 0.1864 0.3622 0.3048 0.036 Uiso 1 1 calc R . . H4C H 0.1636 0.4040 0.3991 0.036 Uiso 1 1 calc R . . C5 C 0.1836(3) 0.7036(3) 0.1903(3) 0.0287(9) Uani 1 1 d . . . H5A H 0.1846 0.7544 0.2303 0.043 Uiso 1 1 calc R . . H5B H 0.1035 0.6952 0.1610 0.043 Uiso 1 1 calc R . . H5C H 0.2383 0.7138 0.1450 0.043 Uiso 1 1 calc R . . C6 C 0.4322(3) 0.6764(2) 0.2969(2) 0.0194(7) Uani 1 1 d . . . H6A H 0.4310 0.7075 0.3546 0.023 Uiso 1 1 calc R . . H6B H 0.4230 0.7202 0.2481 0.023 Uiso 1 1 calc R . . C7 C 0.8111(3) 0.4848(2) 0.4222(2) 0.0201(7) Uani 1 1 d . . . C8 C 0.9094(3) 0.5383(2) 0.4042(2) 0.0211(7) Uani 1 1 d . . . H8 H 0.9905 0.5226 0.4129 0.025 Uiso 1 1 calc R . . C9 C 0.8626(3) 0.6181(2) 0.3713(2) 0.0192(7) Uani 1 1 d . . . C10 C 0.8108(3) 0.3917(2) 0.4583(2) 0.0229(8) Uani 1 1 d . . . H10A H 0.8038 0.3932 0.5227 0.034 Uiso 1 1 calc R . . H10B H 0.8846 0.3623 0.4473 0.034 Uiso 1 1 calc R . . H10C H 0.7436 0.3594 0.4281 0.034 Uiso 1 1 calc R . . C11 C 0.9240(3) 0.7004(3) 0.3409(3) 0.0296(9) Uani 1 1 d . . . H11A H 0.9002 0.7107 0.2773 0.044 Uiso 1 1 calc R . . H11B H 1.0099 0.6924 0.3503 0.044 Uiso 1 1 calc R . . H11C H 0.9013 0.7509 0.3757 0.044 Uiso 1 1 calc R . . C12 C 0.6469(3) 0.6764(2) 0.3453(2) 0.0186(7) Uani 1 1 d . . . H12A H 0.6770 0.7227 0.3074 0.022 Uiso 1 1 calc R . . H12B H 0.6204 0.7042 0.3994 0.022 Uiso 1 1 calc R . . C13 C 0.5735(3) 0.6038(2) 0.2011(2) 0.0183(7) Uani 1 1 d . B . H13A H 0.5103 0.5641 0.1749 0.022 Uiso 1 1 calc R . . H13B H 0.6485 0.5703 0.2059 0.022 Uiso 1 1 calc R . . C14 C 0.5847(4) 0.6818(2) 0.1346(2) 0.0325(10) Uani 1 1 d D . . H14A H 0.5052 0.7055 0.1152 0.039 Uiso 1 1 calc R A 1 H14B H 0.6324 0.7293 0.1652 0.039 Uiso 1 1 calc R A 1 S1 S 0.8018(3) 0.6515(2) 0.0639(3) 0.0333(8) Uani 0.509(5) 1 d PDU B 1 C15 C 0.6441(11) 0.6506(17) 0.0521(9) 0.023(6) Uani 0.509(5) 1 d PDU B 1 C16 C 0.6096(10) 0.6111(9) -0.0281(8) 0.032(4) Uani 0.509(5) 1 d PDU B 1 H16 H 0.5290 0.6013 -0.0488 0.039 Uiso 0.509(5) 1 calc PR B 1 C17 C 0.7066(10) 0.5854(10) -0.0793(8) 0.022(3) Uani 0.509(5) 1 d PDU B 1 H17 H 0.6954 0.5611 -0.1377 0.027 Uiso 0.509(5) 1 calc PR B 1 C18 C 0.8165(11) 0.6002(10) -0.0335(8) 0.030(3) Uani 0.509(5) 1 d PDU B 1 H18 H 0.8896 0.5838 -0.0540 0.036 Uiso 0.509(5) 1 calc PR B 1 S1A S 0.5672(3) 0.61352(19) -0.03827(18) 0.0225(7) Uani 0.491(5) 1 d PDU B 2 C15A C 0.6557(11) 0.6499(17) 0.0582(9) 0.021(6) Uani 0.491(5) 1 d PDU B 2 C16A C 0.7735(13) 0.6426(11) 0.0449(10) 0.045(6) Uani 0.491(5) 1 d PDU B 2 H16A H 0.8370 0.6597 0.0872 0.054 Uiso 0.491(5) 1 calc PR B 2 C17A C 0.7880(11) 0.6049(10) -0.0431(8) 0.026(3) Uani 0.491(5) 1 d PDU B 2 H17A H 0.8631 0.5956 -0.0640 0.031 Uiso 0.491(5) 1 calc PR B 2 C18A C 0.6819(10) 0.5839(10) -0.0933(9) 0.021(3) Uani 0.491(5) 1 d PDU B 2 H18A H 0.6756 0.5568 -0.1504 0.026 Uiso 0.491(5) 1 calc PR B 2 C1S C 0.7533(4) 0.4098(3) 0.1065(3) 0.0320(9) Uani 1 1 d . . . H1S1 H 0.6903 0.4147 0.1471 0.038 Uiso 1 1 calc R . . H1S2 H 0.7408 0.4563 0.0606 0.038 Uiso 1 1 calc R . . Cl1A Cl 0.74556(11) 0.30434(7) 0.05346(7) 0.0409(3) Uani 1 1 d . . . Cl1B Cl 0.89633(13) 0.42411(10) 0.16945(11) 0.0664(4) 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 0.0206(2) 0.0095(2) 0.0143(2) 0.00023(16) 0.00855(17) -0.00012(17) Cl1 0.0320(5) 0.0133(4) 0.0171(4) -0.0014(3) 0.0109(3) 0.0010(3) Cl2 0.0301(4) 0.0119(4) 0.0161(4) 0.0000(3) 0.0114(3) -0.0011(3) N1 0.0217(15) 0.0115(14) 0.0166(14) 0.0011(11) 0.0081(12) 0.0023(11) N2 0.0246(15) 0.0124(14) 0.0194(15) 0.0036(11) 0.0099(12) 0.0017(12) N3 0.0206(14) 0.0125(14) 0.0149(14) -0.0014(11) 0.0097(11) 0.0007(11) N4 0.0220(15) 0.0132(14) 0.0157(14) -0.0003(11) 0.0063(12) -0.0029(12) N5 0.0233(15) 0.0122(14) 0.0211(15) 0.0012(11) 0.0073(12) -0.0029(12) C1 0.0216(17) 0.0190(18) 0.0178(17) -0.0046(13) 0.0086(14) -0.0014(14) C2 0.0183(18) 0.027(2) 0.0222(18) -0.0008(15) 0.0054(14) 0.0002(15) C3 0.0217(18) 0.0269(19) 0.0167(17) -0.0003(14) 0.0061(14) 0.0035(15) C4 0.0243(19) 0.0187(19) 0.028(2) -0.0021(15) 0.0035(15) -0.0033(15) C5 0.029(2) 0.032(2) 0.025(2) 0.0092(16) 0.0027(16) 0.0049(17) C6 0.0270(19) 0.0124(16) 0.0205(17) 0.0032(13) 0.0104(15) 0.0006(14) C7 0.0258(19) 0.0189(18) 0.0167(17) -0.0026(13) 0.0070(14) 0.0009(15) C8 0.0182(17) 0.0247(19) 0.0209(18) -0.0028(14) 0.0054(14) 0.0018(15) C9 0.0160(17) 0.0242(19) 0.0184(17) -0.0033(14) 0.0069(14) -0.0026(14) C10 0.0278(19) 0.0171(18) 0.0245(19) 0.0006(14) 0.0051(15) 0.0044(15) C11 0.028(2) 0.023(2) 0.039(2) 0.0037(17) 0.0095(17) -0.0078(16) C12 0.0246(18) 0.0109(16) 0.0220(17) 0.0013(13) 0.0100(14) -0.0003(14) C13 0.0252(18) 0.0150(17) 0.0161(16) 0.0002(13) 0.0087(14) 0.0008(14) C14 0.059(3) 0.0183(19) 0.024(2) 0.0022(15) 0.0231(19) 0.0010(18) S1 0.0368(15) 0.0354(13) 0.0307(14) -0.0047(11) 0.0179(13) -0.0085(11) C15 0.026(6) 0.022(6) 0.023(6) 0.002(2) 0.006(2) 0.000(2) C16 0.031(5) 0.033(4) 0.034(4) 0.004(2) 0.009(3) 0.000(3) C17 0.026(4) 0.024(4) 0.017(4) -0.001(2) 0.002(3) -0.001(3) C18 0.028(4) 0.032(4) 0.030(4) 0.004(2) 0.009(3) 0.001(3) S1A 0.0271(16) 0.0214(11) 0.0203(11) -0.0018(8) 0.0093(10) -0.0015(10) C15A 0.025(6) 0.018(6) 0.019(6) 0.0022(19) 0.005(2) 0.000(2) C16A 0.049(6) 0.045(6) 0.042(6) -0.002(3) 0.002(3) -0.003(3) C17A 0.022(4) 0.029(4) 0.027(4) 0.004(2) 0.008(3) 0.003(3) C18A 0.025(4) 0.020(4) 0.020(4) -0.001(2) 0.004(3) -0.003(3) C1S 0.039(2) 0.022(2) 0.038(2) -0.0021(17) 0.0163(19) -0.0022(17) Cl1A 0.0573(7) 0.0298(6) 0.0377(6) -0.0100(4) 0.0149(5) -0.0060(5) Cl1B 0.0529(8) 0.0670(9) 0.0767(10) -0.0114(8) -0.0059(7) -0.0226(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N4 2.063(3) . ? Ni1 N1 2.071(3) . ? Ni1 N3 2.235(3) . ? Ni1 Cl1 2.3865(9) . ? Ni1 Cl2 2.3923(9) 3_666 ? Ni1 Cl2 2.4617(9) . ? Cl2 Ni1 2.3922(9) 3_666 ? N1 C1 1.331(4) . ? N1 N2 1.370(4) . ? N2 C3 1.350(4) . ? N2 C6 1.457(4) . ? N3 C6 1.461(4) . ? N3 C12 1.466(4) . ? N3 C13 1.489(4) . ? N4 C7 1.332(4) . ? N4 N5 1.366(4) . ? N5 C9 1.357(4) . ? N5 C12 1.455(4) . ? C1 C2 1.403(5) . ? C1 C4 1.497(5) . ? C2 C3 1.376(5) . ? C3 C5 1.484(5) . ? C7 C8 1.402(5) . ? C7 C10 1.491(5) . ? C8 C9 1.371(5) . ? C9 C11 1.498(5) . ? C13 C14 1.536(5) . ? C14 C15 1.514(5) . ? C14 C15A 1.516(5) . ? S1 C18 1.648(11) . ? S1 C15 1.748(12) . ? C15 C16 1.342(13) . ? C16 C17 1.431(13) . ? C17 C18 1.355(13) . ? S1A C18A 1.641(11) . ? S1A C15A 1.733(13) . ? C15A C16A 1.350(14) . ? C16A C17A 1.437(14) . ? C17A C18A 1.365(13) . ? C1S Cl1A 1.757(4) . ? C1S Cl1B 1.773(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ni1 N1 157.45(11) . . ? N4 Ni1 N3 78.20(11) . . ? N1 Ni1 N3 79.28(10) . . ? N4 Ni1 Cl1 92.92(8) . . ? N1 Ni1 Cl1 91.30(8) . . ? N3 Ni1 Cl1 98.06(7) . . ? N4 Ni1 Cl2 100.15(8) . 3_666 ? N1 Ni1 Cl2 102.06(8) . 3_666 ? N3 Ni1 Cl2 172.75(7) . 3_666 ? Cl1 Ni1 Cl2 89.06(3) . 3_666 ? N4 Ni1 Cl2 89.71(8) . . ? N1 Ni1 Cl2 88.68(8) . . ? N3 Ni1 Cl2 88.71(7) . . ? Cl1 Ni1 Cl2 173.12(3) . . ? Cl2 Ni1 Cl2 84.22(3) 3_666 . ? Ni1 Cl2 Ni1 95.78(3) 3_666 . ? C1 N1 N2 105.4(3) . . ? C1 N1 Ni1 142.0(2) . . ? N2 N1 Ni1 111.8(2) . . ? C3 N2 N1 112.1(3) . . ? C3 N2 C6 128.5(3) . . ? N1 N2 C6 118.9(3) . . ? C6 N3 C12 111.8(3) . . ? C6 N3 C13 113.5(3) . . ? C12 N3 C13 112.1(3) . . ? C6 N3 Ni1 103.71(19) . . ? C12 N3 Ni1 103.00(19) . . ? C13 N3 Ni1 111.82(19) . . ? C7 N4 N5 105.6(3) . . ? C7 N4 Ni1 140.6(2) . . ? N5 N4 Ni1 112.6(2) . . ? C9 N5 N4 111.6(3) . . ? C9 N5 C12 129.9(3) . . ? N4 N5 C12 118.5(3) . . ? N1 C1 C2 110.0(3) . . ? N1 C1 C4 121.3(3) . . ? C2 C1 C4 128.6(3) . . ? C3 C2 C1 106.7(3) . . ? N2 C3 C2 105.8(3) . . ? N2 C3 C5 122.9(3) . . ? C2 C3 C5 131.3(3) . . ? N2 C6 N3 108.4(3) . . ? N4 C7 C8 110.0(3) . . ? N4 C7 C10 121.0(3) . . ? C8 C7 C10 129.0(3) . . ? C9 C8 C7 106.7(3) . . ? N5 C9 C8 106.1(3) . . ? N5 C9 C11 123.2(3) . . ? C8 C9 C11 130.7(3) . . ? N5 C12 N3 107.3(3) . . ? N3 C13 C14 116.0(3) . . ? C15 C14 C15A 5.7(10) . . ? C15 C14 C13 110.4(11) . . ? C15A C14 C13 108.4(10) . . ? C18 S1 C15 95.6(5) . . ? C16 C15 C14 137.1(11) . . ? C16 C15 S1 106.6(6) . . ? C14 C15 S1 115.7(8) . . ? C15 C16 C17 114.7(10) . . ? C18 C17 C16 112.7(11) . . ? C17 C18 S1 110.2(9) . . ? C18A S1A C15A 94.7(5) . . ? C16A C15A C14 136.1(11) . . ? C16A C15A S1A 109.6(7) . . ? C14 C15A S1A 114.3(8) . . ? C15A C16A C17A 111.2(11) . . ? C18A C17A C16A 114.1(11) . . ? C17A C18A S1A 110.2(9) . . ? Cl1A C1S Cl1B 110.0(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.668 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.107 data_b084 _database_code_depnum_ccdc_archive 'CCDC 824465' #TrackingRef 'B084.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H23 Br2 Mg N2 O' _chemical_formula_weight 371.43 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' Mg Mg 0.0486 0.0363 '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 11.4772(12) _cell_length_b 12.3357(12) _cell_length_c 22.480(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3182.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1629 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 19.15 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 5.119 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2339 _exptl_absorpt_correction_T_max 0.6285 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 21206 _diffrn_reflns_av_R_equivalents 0.1035 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3652 _reflns_number_gt 2163 _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^)+(0.0784P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3652 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1096 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1593 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 Mg1 Mg 0.06857(16) 0.86115(14) 0.38033(7) 0.0241(4) Uani 1 1 d . . . Br1 Br 0.13497(6) 0.71836(5) 0.30774(3) 0.0415(2) Uani 1 1 d . . . Br2 Br 0.07983(7) 0.80858(6) 0.48849(3) 0.0532(3) Uani 1 1 d . . . O1 O 0.2295(3) 0.9398(3) 0.38610(16) 0.0328(9) Uani 1 1 d . . . N1 N 0.0059(4) 0.9991(4) 0.3232(2) 0.0323(11) Uani 1 1 d . . . N2 N -0.1220(4) 0.8234(4) 0.3756(2) 0.0364(12) Uani 1 1 d . . . C1 C -0.1210(5) 0.9845(6) 0.3131(3) 0.0512(19) Uani 1 1 d . . . H1A H -0.1641 1.0271 0.3426 0.061 Uiso 1 1 calc R . . H1B H -0.1411 1.0122 0.2736 0.061 Uiso 1 1 calc R . . C2 C -0.1576(6) 0.8695(6) 0.3174(3) 0.0469(17) Uani 1 1 d . . . H2A H -0.1218 0.8277 0.2851 0.056 Uiso 1 1 calc R . . H2B H -0.2425 0.8645 0.3131 0.056 Uiso 1 1 calc R . . C3 C 0.0687(6) 0.9892(6) 0.2656(3) 0.0527(19) Uani 1 1 d . . . H3A H 0.0527 1.0524 0.2413 0.079 Uiso 1 1 calc R . . H3B H 0.0425 0.9246 0.2450 0.079 Uiso 1 1 calc R . . H3C H 0.1518 0.9841 0.2730 0.079 Uiso 1 1 calc R . . C4 C 0.0271(7) 1.1090(5) 0.3466(3) 0.0510(19) Uani 1 1 d . . . H4A H 0.1103 1.1222 0.3487 0.077 Uiso 1 1 calc R . . H4B H -0.0064 1.1153 0.3861 0.077 Uiso 1 1 calc R . . H4C H -0.0087 1.1620 0.3204 0.077 Uiso 1 1 calc R . . C5 C -0.1884(7) 0.8766(6) 0.4239(3) 0.057(2) Uani 1 1 d . . . H5A H -0.1574 0.9486 0.4308 0.085 Uiso 1 1 calc R . . H5B H -0.1816 0.8340 0.4601 0.085 Uiso 1 1 calc R . . H5C H -0.2698 0.8819 0.4127 0.085 Uiso 1 1 calc R . . C6 C -0.1505(6) 0.7064(5) 0.3767(3) 0.0536(19) Uani 1 1 d . . . H6A H -0.2344 0.6972 0.3764 0.080 Uiso 1 1 calc R . . H6B H -0.1184 0.6740 0.4124 0.080 Uiso 1 1 calc R . . H6C H -0.1172 0.6715 0.3420 0.080 Uiso 1 1 calc R . . C7 C 0.2506(6) 1.0248(5) 0.4315(3) 0.0442(16) Uani 1 1 d . . . H7A H 0.1862 1.0284 0.4601 0.053 Uiso 1 1 calc R . . H7B H 0.2606 1.0961 0.4129 0.053 Uiso 1 1 calc R . . C8 C 0.3601(7) 0.9882(7) 0.4607(3) 0.062(2) Uani 1 1 d . . . H8A H 0.3430 0.9372 0.4930 0.075 Uiso 1 1 calc R . . H8B H 0.4029 1.0501 0.4771 0.075 Uiso 1 1 calc R . . C9 C 0.4294(7) 0.9337(6) 0.4124(4) 0.062(2) Uani 1 1 d . . . H9 H 0.5107 0.9303 0.4074 0.074 Uiso 1 1 calc R . . C10 C 0.3379(6) 0.8878(7) 0.3754(4) 0.062(2) Uani 1 1 d . . . H10A H 0.3590 0.8959 0.3334 0.075 Uiso 1 1 calc R . . H10B H 0.3305 0.8102 0.3839 0.075 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 Mg1 0.0303(11) 0.0207(9) 0.0212(9) -0.0012(7) -0.0019(8) -0.0018(8) Br1 0.0478(4) 0.0342(3) 0.0425(4) -0.0127(3) -0.0036(3) 0.0031(3) Br2 0.0733(6) 0.0572(5) 0.0292(4) 0.0132(3) -0.0062(3) -0.0085(4) O1 0.032(3) 0.035(2) 0.032(2) -0.0043(17) -0.0061(17) -0.0058(19) N1 0.026(3) 0.042(3) 0.030(3) 0.008(2) -0.003(2) 0.003(2) N2 0.037(3) 0.038(3) 0.035(3) -0.001(2) 0.005(2) -0.006(2) C1 0.031(4) 0.070(5) 0.053(4) 0.027(4) -0.003(3) -0.002(3) C2 0.036(4) 0.053(4) 0.052(4) 0.007(3) -0.010(3) -0.011(3) C3 0.051(5) 0.077(5) 0.030(4) 0.016(3) 0.004(3) 0.013(4) C4 0.062(5) 0.023(3) 0.068(5) 0.001(3) -0.017(4) 0.005(3) C5 0.048(5) 0.056(5) 0.068(5) -0.010(4) 0.018(4) 0.001(4) C6 0.046(5) 0.046(4) 0.069(5) -0.005(3) 0.005(4) -0.022(3) C7 0.051(4) 0.040(4) 0.042(4) -0.011(3) -0.009(3) -0.010(3) C8 0.059(5) 0.071(5) 0.056(5) -0.001(4) -0.029(4) -0.008(4) C9 0.035(4) 0.065(5) 0.086(6) -0.007(4) -0.018(4) -0.003(4) C10 0.032(4) 0.074(5) 0.082(6) -0.034(4) -0.004(4) -0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mg1 O1 2.091(4) . ? Mg1 N2 2.239(5) . ? Mg1 N1 2.250(5) . ? Mg1 Br1 2.5191(18) . ? Mg1 Br2 2.5197(17) . ? O1 C10 1.420(8) . ? O1 C7 1.482(6) . ? N1 C4 1.476(7) . ? N1 C1 1.484(8) . ? N1 C3 1.486(8) . ? N2 C6 1.480(8) . ? N2 C5 1.481(8) . ? N2 C2 1.483(8) . ? C1 C2 1.483(10) . ? C7 C8 1.488(9) . ? C8 C9 1.506(11) . ? C9 C10 1.454(10) . ? 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 Mg1 N2 164.29(19) . . ? O1 Mg1 N1 88.12(17) . . ? N2 Mg1 N1 79.46(19) . . ? O1 Mg1 Br1 95.59(12) . . ? N2 Mg1 Br1 96.85(14) . . ? N1 Mg1 Br1 104.81(13) . . ? O1 Mg1 Br2 90.82(12) . . ? N2 Mg1 Br2 92.46(14) . . ? N1 Mg1 Br2 139.63(14) . . ? Br1 Mg1 Br2 115.44(7) . . ? C10 O1 C7 107.1(4) . . ? C10 O1 Mg1 123.6(4) . . ? C7 O1 Mg1 121.0(3) . . ? C4 N1 C1 109.1(5) . . ? C4 N1 C3 107.8(5) . . ? C1 N1 C3 109.4(5) . . ? C4 N1 Mg1 116.0(4) . . ? C1 N1 Mg1 108.0(4) . . ? C3 N1 Mg1 106.3(4) . . ? C6 N2 C5 107.8(5) . . ? C6 N2 C2 109.1(5) . . ? C5 N2 C2 109.6(5) . . ? C6 N2 Mg1 114.7(4) . . ? C5 N2 Mg1 112.1(4) . . ? C2 N2 Mg1 103.4(4) . . ? C2 C1 N1 112.6(6) . . ? C1 C2 N2 110.2(5) . . ? O1 C7 C8 103.1(5) . . ? C7 C8 C9 105.2(6) . . ? C10 C9 C8 101.8(6) . . ? O1 C10 C9 111.1(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.657 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.138