# Electronic Supplementary Material (ESI) for RSC Advances # 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_YCP8_CdBripBitmb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H45 Br2 Cd2 N4 O13' _chemical_formula_weight 1186.43 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.285(2) _cell_length_b 11.947(2) _cell_length_c 32.654(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.262(4) _cell_angle_gamma 90.00 _cell_volume 4399.1(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5330 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.56 _exptl_crystal_description PLATES _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2356 _exptl_absorpt_coefficient_mu 2.852 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5600 _exptl_absorpt_correction_T_max 0.8475 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex ccd diffractometer' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30525 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0680 _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 -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7756 _reflns_number_gt 6489 _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 ORTEP _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+67.4437P] 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 7756 _refine_ls_number_parameters 569 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.1788 _refine_ls_wR_factor_gt 0.1724 _refine_ls_goodness_of_fit_ref 1.239 _refine_ls_restrained_S_all 1.238 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.20044(6) 0.93562(6) 0.17290(2) 0.01388(19) Uani 1 d . . . Cd2 Cd -0.04865(6) 1.14457(6) 0.18304(2) 0.0143(2) Uani 1 d . . . Br1 Br 0.29143(13) 0.46125(10) 0.01780(4) 0.0394(4) Uani 1 d . . . Br2 Br -0.12856(10) 0.54749(9) 0.09251(3) 0.0266(3) Uani 1 d . . . N1 N 0.3926(7) 0.9507(7) 0.1929(3) 0.021(2) Uani 1 d . . . N2 N 0.5549(8) 0.9734(8) 0.2322(3) 0.025(2) Uani 1 d . . . N3 N 0.3958(7) 0.6900(7) 0.3811(3) 0.021(2) Uani 1 d . . . N4 N 0.2163(8) 0.6496(7) 0.3578(3) 0.022(2) Uani 1 d . . . O1 O 0.2270(7) 0.7986(6) 0.1234(2) 0.0262(18) Uani 1 d . . . O2 O 0.1813(6) 0.7302(5) 0.1827(2) 0.0188(16) Uani 1 d . . . O3 O 0.0219(7) 0.3319(6) 0.1819(2) 0.0239(17) Uani 1 d . . . O4 O 0.0678(6) 0.2214(6) 0.1311(2) 0.0210(17) Uani 1 d . . . O5 O -0.0059(6) 0.9541(5) 0.1582(2) 0.0177(16) Uani 1 d . . . O6 O -0.1171(6) 0.9722(6) 0.2115(2) 0.0211(17) Uani 1 d . . . O7 O -0.1389(6) 0.6011(5) 0.2889(2) 0.0145(15) Uani 1 d . . . O8 O -0.1743(6) 0.4471(5) 0.2531(2) 0.0188(16) Uani 1 d . . . O9 O 0.2316(6) 1.0595(6) 0.1203(2) 0.0249(17) Uani 1 d D . . H9C H 0.208(10) 1.023(9) 0.096(2) 0.050 Uiso 1 d D . . H9D H 0.172(8) 1.111(8) 0.127(3) 0.050 Uiso 1 d D . . O10 O -0.1548(6) 1.2244(6) 0.2341(2) 0.0211(17) Uani 1 d D . . H10C H -0.121(9) 1.297(5) 0.237(4) 0.050 Uiso 1 d D . . H10D H -0.227(6) 1.224(9) 0.248(4) 0.050 Uiso 1 d D . . O11 O 0.2053(10) 0.9277(8) 0.0533(3) 0.053(3) Uani 1 d . . . O12 O 0.5274(10) 0.6698(11) 0.4857(3) 0.067(3) Uani 1 d . . . O13 O -0.0004(10) 0.6350(9) 0.5093(3) 0.063(3) Uani 1 d . . . C1 C 0.2029(8) 0.7180(9) 0.1461(3) 0.018(2) Uani 1 d . . . C2 C 0.1979(8) 0.6018(8) 0.1277(3) 0.014(2) Uani 1 d . . . C3 C 0.2416(9) 0.5862(8) 0.0887(3) 0.017(2) Uani 1 d . . . H3 H 0.2762 0.6450 0.0749 0.020 Uiso 1 calc R . . C4 C 0.2320(9) 0.4805(9) 0.0711(3) 0.020(2) Uani 1 d . . . C5 C 0.1825(9) 0.3930(9) 0.0901(3) 0.019(2) Uani 1 d . . . H5 H 0.1776 0.3234 0.0774 0.023 Uiso 1 calc R . . C6 C 0.1385(9) 0.4082(8) 0.1291(3) 0.016(2) Uani 1 d . . . C7 C 0.1480(9) 0.5133(8) 0.1478(3) 0.015(2) Uani 1 d . . . H7 H 0.1204 0.5235 0.1740 0.018 Uiso 1 calc R . . C8 C 0.0718(9) 0.3153(8) 0.1487(3) 0.017(2) Uani 1 d . . . C9 C -0.0714(8) 0.9138(8) 0.1849(3) 0.014(2) Uani 1 d . . . C10 C -0.1009(8) 0.7887(8) 0.1828(3) 0.012(2) Uiso 1 d . . . C11 C -0.1012(8) 0.7359(9) 0.1451(3) 0.019(2) Uani 1 d . . . H11 H -0.0860 0.7752 0.1212 0.023 Uiso 1 calc R . . C12 C -0.1246(9) 0.6234(9) 0.1442(3) 0.020(2) Uani 1 d . . . C13 C -0.1414(9) 0.5624(9) 0.1786(3) 0.020(2) Uani 1 d . . . H13 H -0.1554 0.4858 0.1766 0.024 Uiso 1 calc R . . C14 C -0.1376(8) 0.6135(8) 0.2163(3) 0.016(2) Uani 1 d . . . C15 C -0.1190(8) 0.7312(9) 0.2183(3) 0.017(2) Uani 1 d . . . H15 H -0.1190 0.7685 0.2433 0.020 Uiso 1 calc R . . C16 C -0.1492(8) 0.5505(8) 0.2550(3) 0.015(2) Uani 1 d . . . C17 C 0.4899(9) 0.9600(9) 0.1686(4) 0.021(2) Uani 1 d . . . H17 H 0.4873 0.9554 0.1402 0.026 Uiso 1 calc R . . C18 C 0.5884(9) 0.9767(10) 0.1921(4) 0.028(3) Uani 1 d . . . H18 H 0.6646 0.9882 0.1830 0.034 Uiso 1 calc R . . C19 C 0.4357(9) 0.9572(9) 0.2306(4) 0.021(2) Uani 1 d . . . H19 H 0.3902 0.9515 0.2537 0.025 Uiso 1 calc R . . C20 C 0.6303(10) 0.9923(11) 0.2686(4) 0.034(3) Uani 1 d . . . H20A H 0.6588 1.0688 0.2685 0.041 Uiso 1 calc R . . H20B H 0.6987 0.9432 0.2678 0.041 Uiso 1 calc R . . C21 C 0.5676(9) 0.9716(9) 0.3079(4) 0.021(2) Uani 1 d . . . C22 C 0.5700(9) 0.8673(9) 0.3261(3) 0.022(2) Uani 1 d . . . C23 C 0.5179(9) 0.8505(9) 0.3640(3) 0.021(2) Uani 1 d . . . C24 C 0.4674(10) 0.9425(11) 0.3835(4) 0.030(3) Uani 1 d . . . C25 C 0.4598(11) 1.0436(11) 0.3636(4) 0.036(3) Uani 1 d . . . H25 H 0.4192 1.1021 0.3756 0.043 Uiso 1 calc R . . C26 C 0.5103(10) 1.0611(9) 0.3265(4) 0.028(3) Uani 1 d . . . C27 C 0.5157(9) 0.7382(9) 0.3841(4) 0.024(3) Uani 1 d . . . H27A H 0.5708 0.6885 0.3711 0.029 Uiso 1 calc R . . H27B H 0.5408 0.7455 0.4128 0.029 Uiso 1 calc R . . C28 C 0.3529(10) 0.6092(9) 0.4063(4) 0.027(3) Uani 1 d . . . H28 H 0.3917 0.5764 0.4289 0.032 Uiso 1 calc R . . C29 C 0.2413(10) 0.5876(10) 0.3912(4) 0.028(3) Uani 1 d . . . H29 H 0.1894 0.5367 0.4024 0.033 Uiso 1 calc R . . C30 C 0.3106(9) 0.7113(9) 0.3521(3) 0.020(2) Uani 1 d . . . H30 H 0.3175 0.7628 0.3310 0.024 Uiso 1 calc R . . C31 C 0.6246(10) 0.7683(10) 0.3043(4) 0.029(3) Uani 1 d . . . H31A H 0.6431 0.7899 0.2769 0.043 Uiso 1 calc R . . H31B H 0.5693 0.7072 0.3032 0.043 Uiso 1 calc R . . H31C H 0.6959 0.7455 0.3190 0.043 Uiso 1 calc R . . C32 C 0.4146(13) 0.9305(13) 0.4248(4) 0.050(4) Uani 1 d . . . H32A H 0.3826 1.0012 0.4330 0.075 Uiso 1 calc R . . H32B H 0.4750 0.9072 0.4445 0.075 Uiso 1 calc R . . H32C H 0.3525 0.8756 0.4233 0.075 Uiso 1 calc R . . C33 C 0.4985(14) 1.1742(11) 0.3062(5) 0.055(4) Uani 1 d . . . H33A H 0.4382 1.2168 0.3190 0.082 Uiso 1 calc R . . H33B H 0.4771 1.1644 0.2776 0.082 Uiso 1 calc R . . H33C H 0.5727 1.2132 0.3088 0.082 Uiso 1 calc R . . C34 C 0.6374(14) 0.6382(15) 0.5055(5) 0.062(5) Uani 1 d . . . H34A H 0.7034 0.6695 0.4911 0.075 Uiso 1 calc R . . H34B H 0.6454 0.5574 0.5060 0.075 Uiso 1 calc R . . C35 C 0.6351(13) 0.6838(13) 0.5480(5) 0.057(4) Uani 1 d . . . H35A H 0.6771 0.6353 0.5675 0.068 Uiso 1 calc R . . H35B H 0.6690 0.7584 0.5497 0.068 Uiso 1 calc R . . C36 C 0.5055(17) 0.6855(18) 0.5550(6) 0.081(6) Uani 1 d . . . H36 H 0.4675 0.6719 0.5792 0.097 Uiso 1 calc R . . C37 C 0.4535(15) 0.7127(19) 0.5161(5) 0.078(6) Uani 1 d . . . H37A H 0.4460 0.7932 0.5133 0.094 Uiso 1 calc R . . H37B H 0.3750 0.6799 0.5131 0.094 Uiso 1 calc R . . C38 C -0.0198(18) 0.7414(13) 0.5246(7) 0.081(6) Uani 1 d . . . H38A H 0.0164 0.7490 0.5519 0.098 Uiso 1 calc R . . H38B H -0.1042 0.7558 0.5260 0.098 Uiso 1 calc R . . C39 C 0.0358(16) 0.8224(13) 0.4953(5) 0.064(5) Uani 1 d . . . H39A H -0.0238 0.8713 0.4828 0.077 Uiso 1 calc R . . H39B H 0.0955 0.8679 0.5096 0.077 Uiso 1 calc R . . C40 C 0.0903(16) 0.7512(15) 0.4640(5) 0.064(5) Uani 1 d . . . H40A H 0.1745 0.7409 0.4699 0.076 Uiso 1 calc R . . H40B H 0.0783 0.7825 0.4367 0.076 Uiso 1 calc R . . C41 C 0.024(2) 0.6442(13) 0.4684(5) 0.072(6) Uani 1 d . . . H41A H -0.0493 0.6458 0.4517 0.087 Uiso 1 calc R . . H41B H 0.0712 0.5814 0.4599 0.087 Uiso 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 Cd1 0.0113(4) 0.0087(4) 0.0219(4) -0.0020(3) 0.0044(3) -0.0001(3) Cd2 0.0114(4) 0.0081(4) 0.0237(4) 0.0007(3) 0.0033(3) 0.0006(3) Br1 0.0579(9) 0.0259(7) 0.0364(7) -0.0102(6) 0.0277(6) -0.0093(6) Br2 0.0322(7) 0.0235(6) 0.0241(6) -0.0059(5) -0.0005(5) -0.0007(5) N1 0.013(4) 0.017(5) 0.034(6) 0.002(4) 0.005(4) 0.002(4) N2 0.019(5) 0.018(5) 0.039(6) 0.009(4) 0.002(4) -0.003(4) N3 0.013(5) 0.023(5) 0.027(5) -0.001(4) 0.002(4) 0.000(4) N4 0.021(5) 0.020(5) 0.024(5) 0.002(4) 0.005(4) 0.001(4) O1 0.037(5) 0.012(4) 0.030(5) 0.003(3) 0.007(4) -0.009(3) O2 0.028(4) 0.006(3) 0.024(4) 0.003(3) 0.010(3) -0.006(3) O3 0.024(4) 0.016(4) 0.033(5) -0.001(3) 0.011(3) -0.001(3) O4 0.024(4) 0.011(4) 0.028(4) 0.001(3) 0.000(3) -0.003(3) O5 0.015(4) 0.012(4) 0.027(4) 0.009(3) 0.008(3) -0.004(3) O6 0.019(4) 0.010(4) 0.034(5) -0.001(3) 0.003(3) 0.002(3) O7 0.008(3) 0.012(3) 0.023(4) -0.002(3) 0.002(3) 0.001(3) O8 0.027(4) 0.005(3) 0.025(4) 0.000(3) 0.012(3) 0.003(3) O9 0.019(4) 0.023(4) 0.033(5) 0.000(4) 0.008(3) 0.003(3) O10 0.016(4) 0.009(3) 0.039(5) -0.009(3) 0.012(3) 0.002(3) O11 0.074(7) 0.044(6) 0.040(6) 0.005(5) 0.005(5) -0.001(5) O12 0.051(7) 0.095(9) 0.056(7) -0.003(7) -0.002(6) 0.001(6) O13 0.065(7) 0.060(7) 0.066(8) 0.004(6) 0.011(6) 0.015(6) C1 0.002(5) 0.026(6) 0.026(6) -0.002(5) -0.004(4) 0.002(4) C2 0.003(5) 0.013(5) 0.027(6) -0.002(4) 0.001(4) 0.002(4) C3 0.022(6) 0.007(5) 0.021(6) 0.000(4) 0.004(4) 0.001(4) C4 0.020(6) 0.026(6) 0.016(6) 0.003(5) 0.010(4) 0.006(5) C5 0.009(5) 0.018(5) 0.030(6) -0.008(5) -0.003(4) 0.000(4) C6 0.018(5) 0.013(5) 0.016(5) 0.000(4) -0.001(4) 0.004(4) C7 0.012(5) 0.015(5) 0.018(5) 0.003(4) 0.000(4) 0.001(4) C8 0.018(6) 0.009(5) 0.022(6) -0.004(4) 0.001(4) 0.003(4) C9 0.009(5) 0.006(5) 0.025(6) 0.007(4) -0.006(4) -0.001(4) C11 0.003(5) 0.023(6) 0.032(6) 0.008(5) 0.000(4) -0.005(4) C12 0.012(5) 0.025(6) 0.022(6) -0.006(5) 0.001(4) -0.004(4) C13 0.017(5) 0.017(5) 0.025(6) 0.013(5) 0.002(4) -0.004(4) C14 0.009(5) 0.010(5) 0.030(6) 0.006(4) 0.004(4) 0.000(4) C15 0.007(5) 0.021(6) 0.023(6) 0.000(5) 0.002(4) 0.001(4) C16 0.007(5) 0.015(5) 0.024(6) 0.001(5) 0.004(4) 0.004(4) C17 0.012(5) 0.021(6) 0.032(6) 0.002(5) 0.006(5) 0.011(4) C18 0.004(5) 0.036(7) 0.044(7) 0.007(6) 0.009(5) -0.002(5) C19 0.007(5) 0.025(6) 0.031(7) 0.006(5) 0.007(5) 0.000(4) C20 0.016(6) 0.046(8) 0.039(8) 0.012(6) -0.004(5) -0.010(5) C21 0.008(5) 0.016(5) 0.038(7) 0.001(5) -0.004(5) -0.003(4) C22 0.011(5) 0.024(6) 0.031(7) 0.005(5) -0.007(5) -0.005(4) C23 0.010(5) 0.023(6) 0.030(6) 0.000(5) -0.006(4) 0.006(4) C24 0.017(6) 0.038(7) 0.034(7) -0.013(6) -0.009(5) -0.002(5) C25 0.032(7) 0.033(7) 0.041(8) -0.012(6) -0.008(6) 0.002(6) C26 0.024(6) 0.014(6) 0.046(8) 0.000(5) -0.011(5) -0.004(5) C27 0.007(5) 0.025(6) 0.038(7) 0.006(5) -0.002(5) 0.007(4) C28 0.030(7) 0.020(6) 0.030(7) 0.002(5) 0.006(5) 0.002(5) C29 0.022(6) 0.029(7) 0.032(7) -0.004(5) 0.008(5) 0.004(5) C30 0.014(5) 0.020(6) 0.027(6) 0.007(5) 0.001(5) 0.004(4) C31 0.027(7) 0.031(7) 0.027(7) -0.002(5) 0.000(5) 0.009(5) C32 0.050(9) 0.058(10) 0.043(9) 0.001(7) 0.002(7) 0.021(8) C33 0.048(9) 0.027(7) 0.088(12) 0.010(8) -0.019(8) -0.006(6) C34 0.051(10) 0.056(10) 0.080(13) -0.009(9) 0.003(9) 0.010(8) C35 0.046(9) 0.050(9) 0.073(12) 0.010(8) -0.028(8) -0.007(7) C36 0.071(13) 0.115(17) 0.056(12) 0.006(11) -0.001(10) 0.026(12) C37 0.039(10) 0.124(18) 0.071(13) 0.022(12) 0.008(9) 0.012(10) C38 0.084(14) 0.036(9) 0.127(18) -0.027(10) 0.040(12) 0.012(9) C39 0.077(13) 0.039(9) 0.075(12) -0.004(9) -0.012(10) 0.000(8) C40 0.064(11) 0.072(12) 0.055(10) 0.011(9) -0.001(9) -0.006(9) C41 0.147(19) 0.036(9) 0.033(9) 0.000(7) -0.010(10) 0.003(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N1 2.247(9) . ? Cd1 O9 2.304(8) . ? Cd1 O1 2.328(7) . ? Cd1 O5 2.369(7) . ? Cd1 O8 2.450(7) 2 ? Cd1 O7 2.452(7) 2 ? Cd1 O2 2.486(6) . ? Cd1 C1 2.743(11) . ? Cd2 N4 2.272(9) 2 ? Cd2 O10 2.299(7) . ? Cd2 O7 2.331(7) 2 ? Cd2 O4 2.371(7) 1_565 ? Cd2 O3 2.376(7) 1_565 ? Cd2 O6 2.399(7) . ? Cd2 O5 2.470(7) . ? Cd2 C8 2.719(10) 1_565 ? Br1 C4 1.905(10) . ? Br2 C12 1.916(10) . ? N1 C19 1.308(14) . ? N1 C17 1.385(13) . ? N2 C19 1.357(13) . ? N2 C18 1.379(15) . ? N2 C20 1.453(15) . ? N3 C30 1.345(14) . ? N3 C28 1.369(14) . ? N3 C27 1.471(13) . ? N4 C30 1.314(13) . ? N4 C29 1.338(14) . ? N4 Cd2 2.272(9) 2_545 ? O1 C1 1.251(13) . ? O2 C1 1.238(12) . ? O3 C8 1.257(12) . ? O3 Cd2 2.376(7) 1_545 ? O4 C8 1.261(12) . ? O4 Cd2 2.371(7) 1_545 ? O5 C9 1.262(12) . ? O6 C9 1.240(12) . ? O7 C16 1.264(12) . ? O7 Cd2 2.331(6) 2_545 ? O7 Cd1 2.452(7) 2_545 ? O8 C16 1.268(12) . ? O8 Cd1 2.450(7) 2_545 ? O9 H9C 0.95(2) . ? O9 H9D 0.95(2) . ? O10 H10C 0.95(2) . ? O10 H10D 0.95(2) . ? O12 C37 1.417(19) . ? O12 C34 1.427(18) . ? O13 C41 1.378(18) . ? O13 C38 1.386(18) . ? C1 C2 1.513(14) . ? C2 C7 1.375(14) . ? C2 C3 1.397(14) . ? C3 C4 1.389(15) . ? C3 H3 0.9300 . ? C4 C5 1.348(15) . ? C5 C6 1.398(14) . ? C5 H5 0.9300 . ? C6 C7 1.398(14) . ? C6 C8 1.497(14) . ? C7 H7 0.9300 . ? C8 Cd2 2.719(10) 1_545 ? C9 C10 1.533(13) . ? C10 C15 1.371(14) . ? C10 C11 1.383(14) . ? C11 C12 1.369(15) . ? C11 H11 0.9300 . ? C12 C13 1.358(15) . ? C13 C14 1.374(15) . ? C13 H13 0.9300 . ? C14 C15 1.422(14) . ? C14 C16 1.480(14) . ? C15 H15 0.9300 . ? C17 C18 1.339(16) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.509(16) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.381(15) . ? C21 C26 1.402(16) . ? C22 C23 1.405(15) . ? C22 C31 1.523(16) . ? C23 C24 1.402(16) . ? C23 C27 1.495(15) . ? C24 C25 1.374(18) . ? C24 C32 1.501(18) . ? C25 C26 1.374(18) . ? C25 H25 0.9300 . ? C26 C33 1.509(17) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.359(16) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C35 1.49(2) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.49(2) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.41(2) . ? C36 H36 0.9300 . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.51(2) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.48(2) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C41 1.49(2) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 O9 89.5(3) . . ? N1 Cd1 O1 96.3(3) . . ? O9 Cd1 O1 84.7(3) . . ? N1 Cd1 O5 168.8(3) . . ? O9 Cd1 O5 88.1(2) . . ? O1 Cd1 O5 94.4(3) . . ? N1 Cd1 O8 82.0(3) . 2 ? O9 Cd1 O8 136.6(2) . 2 ? O1 Cd1 O8 138.4(2) . 2 ? O5 Cd1 O8 92.3(2) . 2 ? N1 Cd1 O7 94.4(3) . 2 ? O9 Cd1 O7 85.2(2) . 2 ? O1 Cd1 O7 165.2(3) . 2 ? O5 Cd1 O7 74.5(2) . 2 ? O8 Cd1 O7 53.6(2) 2 2 ? N1 Cd1 O2 97.4(3) . . ? O9 Cd1 O2 138.3(3) . . ? O1 Cd1 O2 53.8(2) . . ? O5 Cd1 O2 91.6(2) . . ? O8 Cd1 O2 85.0(2) 2 . ? O7 Cd1 O2 134.6(2) 2 . ? N1 Cd1 C1 98.4(3) . . ? O9 Cd1 C1 111.5(3) . . ? O1 Cd1 C1 27.0(3) . . ? O5 Cd1 C1 92.6(3) . . ? O8 Cd1 C1 111.8(3) 2 . ? O7 Cd1 C1 158.9(3) 2 . ? O2 Cd1 C1 26.8(3) . . ? N4 Cd2 O10 88.3(3) 2 . ? N4 Cd2 O7 163.4(3) 2 2 ? O10 Cd2 O7 107.4(3) . 2 ? N4 Cd2 O4 92.4(3) 2 1_565 ? O10 Cd2 O4 132.7(2) . 1_565 ? O7 Cd2 O4 81.2(2) 2 1_565 ? N4 Cd2 O3 103.7(3) 2 1_565 ? O10 Cd2 O3 78.8(2) . 1_565 ? O7 Cd2 O3 85.2(2) 2 1_565 ? O4 Cd2 O3 55.1(2) 1_565 1_565 ? N4 Cd2 O6 88.6(3) 2 . ? O10 Cd2 O6 83.7(2) . . ? O7 Cd2 O6 87.6(2) 2 . ? O4 Cd2 O6 143.6(2) 1_565 . ? O3 Cd2 O6 158.1(3) 1_565 . ? N4 Cd2 O5 90.0(3) 2 . ? O10 Cd2 O5 137.3(2) . . ? O7 Cd2 O5 74.8(2) 2 . ? O4 Cd2 O5 90.0(2) 1_565 . ? O3 Cd2 O5 142.4(2) 1_565 . ? O6 Cd2 O5 53.6(2) . . ? N4 Cd2 C8 99.0(3) 2 1_565 ? O10 Cd2 C8 105.8(3) . 1_565 ? O7 Cd2 C8 82.4(3) 2 1_565 ? O4 Cd2 C8 27.6(3) 1_565 1_565 ? O3 Cd2 C8 27.5(3) 1_565 1_565 ? O6 Cd2 C8 167.9(3) . 1_565 ? O5 Cd2 C8 116.6(3) . 1_565 ? C19 N1 C17 105.1(9) . . ? C19 N1 Cd1 126.7(7) . . ? C17 N1 Cd1 128.1(8) . . ? C19 N2 C18 106.1(9) . . ? C19 N2 C20 126.9(10) . . ? C18 N2 C20 126.9(9) . . ? C30 N3 C28 107.2(9) . . ? C30 N3 C27 127.1(9) . . ? C28 N3 C27 125.5(9) . . ? C30 N4 C29 106.2(9) . . ? C30 N4 Cd2 126.3(7) . 2_545 ? C29 N4 Cd2 127.4(8) . 2_545 ? C1 O1 Cd1 95.3(6) . . ? C1 O2 Cd1 88.3(6) . . ? C8 O3 Cd2 91.6(6) . 1_545 ? C8 O4 Cd2 91.7(6) . 1_545 ? C9 O5 Cd1 115.0(6) . . ? C9 O5 Cd2 89.8(6) . . ? Cd1 O5 Cd2 102.8(3) . . ? C9 O6 Cd2 93.6(6) . . ? C16 O7 Cd2 120.1(6) . 2_545 ? C16 O7 Cd1 92.4(6) . 2_545 ? Cd2 O7 Cd1 104.6(3) 2_545 2_545 ? C16 O8 Cd1 92.4(6) . 2_545 ? Cd1 O9 H9C 107(8) . . ? Cd1 O9 H9D 97(8) . . ? H9C O9 H9D 108(3) . . ? Cd2 O10 H10C 103(6) . . ? Cd2 O10 H10D 146(7) . . ? H10C O10 H10D 108(3) . . ? C37 O12 C34 107.8(12) . . ? C41 O13 C38 108.3(13) . . ? O2 C1 O1 122.5(10) . . ? O2 C1 C2 119.0(9) . . ? O1 C1 C2 118.4(9) . . ? O2 C1 Cd1 64.9(5) . . ? O1 C1 Cd1 57.7(5) . . ? C2 C1 Cd1 174.6(7) . . ? C7 C2 C3 119.8(9) . . ? C7 C2 C1 121.7(9) . . ? C3 C2 C1 118.4(9) . . ? C4 C3 C2 118.3(9) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C5 C4 C3 122.9(10) . . ? C5 C4 Br1 119.5(8) . . ? C3 C4 Br1 117.6(8) . . ? C4 C5 C6 119.1(10) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C7 C6 C5 119.3(9) . . ? C7 C6 C8 120.8(9) . . ? C5 C6 C8 119.6(9) . . ? C2 C7 C6 120.6(9) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? O3 C8 O4 121.5(9) . . ? O3 C8 C6 120.1(9) . . ? O4 C8 C6 118.4(9) . . ? O3 C8 Cd2 60.9(5) . 1_545 ? O4 C8 Cd2 60.6(5) . 1_545 ? C6 C8 Cd2 179.1(7) . 1_545 ? O6 C9 O5 122.7(9) . . ? O6 C9 C10 119.0(9) . . ? O5 C9 C10 118.2(9) . . ? C15 C10 C11 122.0(9) . . ? C15 C10 C9 119.3(9) . . ? C11 C10 C9 118.6(9) . . ? C12 C11 C10 117.3(10) . . ? C12 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? C13 C12 C11 122.9(10) . . ? C13 C12 Br2 118.3(8) . . ? C11 C12 Br2 118.7(8) . . ? C12 C13 C14 120.1(10) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 118.7(9) . . ? C13 C14 C16 122.5(9) . . ? C15 C14 C16 118.8(10) . . ? C10 C15 C14 118.9(10) . . ? C10 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? O7 C16 O8 121.4(9) . . ? O7 C16 C14 119.8(9) . . ? O8 C16 C14 118.7(9) . . ? C18 C17 N1 110.1(10) . . ? C18 C17 H17 124.9 . . ? N1 C17 H17 124.9 . . ? C17 C18 N2 106.6(9) . . ? C17 C18 H18 126.7 . . ? N2 C18 H18 126.7 . . ? N1 C19 N2 112.0(10) . . ? N1 C19 H19 124.0 . . ? N2 C19 H19 124.0 . . ? N2 C20 C21 113.0(9) . . ? N2 C20 H20A 109.0 . . ? C21 C20 H20A 109.0 . . ? N2 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C26 120.2(11) . . ? C22 C21 C20 120.8(10) . . ? C26 C21 C20 119.0(10) . . ? C21 C22 C23 120.4(10) . . ? C21 C22 C31 120.1(10) . . ? C23 C22 C31 119.5(10) . . ? C24 C23 C22 118.8(11) . . ? C24 C23 C27 119.3(10) . . ? C22 C23 C27 122.0(10) . . ? C25 C24 C23 119.5(12) . . ? C25 C24 C32 119.3(12) . . ? C23 C24 C32 121.1(12) . . ? C26 C25 C24 122.1(12) . . ? C26 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C25 C26 C21 118.8(11) . . ? C25 C26 C33 119.5(12) . . ? C21 C26 C33 121.7(12) . . ? N3 C27 C23 110.7(8) . . ? N3 C27 H27A 109.5 . . ? C23 C27 H27A 109.5 . . ? N3 C27 H27B 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 108.1 . . ? C29 C28 N3 105.1(10) . . ? C29 C28 H28 127.5 . . ? N3 C28 H28 127.5 . . ? N4 C29 C28 110.7(11) . . ? N4 C29 H29 124.7 . . ? C28 C29 H29 124.7 . . ? N4 C30 N3 110.8(9) . . ? N4 C30 H30 124.6 . . ? N3 C30 H30 124.6 . . ? C22 C31 H31A 109.5 . . ? C22 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C22 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C24 C32 H32A 109.5 . . ? C24 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C24 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C26 C33 H33A 109.5 . . ? C26 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C26 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O12 C34 C35 106.1(12) . . ? O12 C34 H34A 110.5 . . ? C35 C34 H34A 110.5 . . ? O12 C34 H34B 110.5 . . ? C35 C34 H34B 110.5 . . ? H34A C34 H34B 108.7 . . ? C36 C35 C34 101.5(13) . . ? C36 C35 H35A 111.5 . . ? C34 C35 H35A 111.5 . . ? C36 C35 H35B 111.5 . . ? C34 C35 H35B 111.5 . . ? H35A C35 H35B 109.3 . . ? C37 C36 C35 104.0(16) . . ? C37 C36 H36 128.0 . . ? C35 C36 H36 128.0 . . ? C36 C37 O12 108.1(15) . . ? C36 C37 H37A 110.1 . . ? O12 C37 H37A 110.1 . . ? C36 C37 H37B 110.1 . . ? O12 C37 H37B 110.1 . . ? H37A C37 H37B 108.4 . . ? O13 C38 C39 106.5(14) . . ? O13 C38 H38A 110.4 . . ? C39 C38 H38A 110.4 . . ? O13 C38 H38B 110.4 . . ? C39 C38 H38B 110.4 . . ? H38A C38 H38B 108.6 . . ? C40 C39 C38 105.2(13) . . ? C40 C39 H39A 110.7 . . ? C38 C39 H39A 110.7 . . ? C40 C39 H39B 110.7 . . ? C38 C39 H39B 110.7 . . ? H39A C39 H39B 108.8 . . ? C39 C40 C41 101.6(14) . . ? C39 C40 H40A 111.5 . . ? C41 C40 H40A 111.5 . . ? C39 C40 H40B 111.5 . . ? C41 C40 H40B 111.5 . . ? H40A C40 H40B 109.3 . . ? O13 C41 C40 106.4(13) . . ? O13 C41 H41A 110.5 . . ? C40 C41 H41A 110.5 . . ? O13 C41 H41B 110.5 . . ? C40 C41 H41B 110.5 . . ? H41A C41 H41B 108.6 . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 2.896 _refine_diff_density_min -1.315 _refine_diff_density_rms 0.197 _database_code_depnum_ccdc_archive 'CCDC 939331' ####################################################################### # # 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_ycp24m_CuBripBitmb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H25 Br Cu N4 O5' _chemical_formula_weight 604.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.298(3) _cell_length_b 10.903(3) _cell_length_c 13.375(4) _cell_angle_alpha 75.732(5) _cell_angle_beta 76.533(5) _cell_angle_gamma 70.130(5) _cell_volume 1219.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1994 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 24.12 _exptl_crystal_description PLATES _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 614 _exptl_absorpt_coefficient_mu 2.579 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8010 _exptl_absorpt_correction_T_max 0.9502 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRCTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10411 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0842 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5387 _reflns_number_gt 4088 _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 ORTEP _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^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 5387 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Cu1 Cu 0.60083(5) 0.84827(4) 0.17785(4) 0.01529(14) Uani 1 1 d . . . Br1 Br 0.57919(7) 1.24564(5) 0.54242(4) 0.03720(16) Uani 1 1 d . . . N1 N 0.8267(4) 0.7838(3) 0.1414(3) 0.0185(7) Uani 1 1 d . . . N2 N 1.0686(4) 0.6599(3) 0.1359(3) 0.0188(7) Uani 1 1 d . . . N3 N 1.1406(4) 0.0444(3) 0.2614(3) 0.0177(7) Uani 1 1 d . . . N4 N 1.3736(4) -0.0823(3) 0.2107(2) 0.0158(7) Uani 1 1 d . . . O1 O 0.6154(3) 0.9935(3) 0.2367(2) 0.0196(6) Uani 1 1 d . . . O2 O 0.6506(3) 1.1243(3) 0.0813(2) 0.0220(6) Uani 1 1 d . . . O3 O 0.5921(3) 1.6567(2) 0.2267(2) 0.0183(6) Uani 1 1 d . . . O4 O 0.6470(4) 1.5857(3) 0.0742(2) 0.0342(8) Uani 1 1 d . . . O5 O 0.5971(4) 0.8507(3) 0.0119(2) 0.0210(6) Uani 1 1 d . . . H5C H 0.621(5) 0.763(5) 0.027(3) 0.020(11) Uiso 1 1 d . . . H5D H 0.527(6) 0.882(5) -0.017(4) 0.029(15) Uiso 1 1 d . . . C1 C 0.6302(4) 1.1008(4) 0.1780(3) 0.0157(8) Uani 1 1 d . . . C2 C 0.6223(4) 1.2085(4) 0.2350(3) 0.0161(8) Uani 1 1 d . . . C3 C 0.6072(4) 1.1824(4) 0.3435(3) 0.0186(8) Uani 1 1 d . . . H3 H 0.6003 1.1002 0.3815 0.022 Uiso 1 1 calc R . . C4 C 0.6026(5) 1.2808(4) 0.3941(3) 0.0185(8) Uani 1 1 d . . . C5 C 0.6110(4) 1.4045(4) 0.3396(3) 0.0181(8) Uani 1 1 d . . . H5 H 0.6095 1.4686 0.3749 0.022 Uiso 1 1 calc R . . C6 C 0.6217(4) 1.4314(4) 0.2321(3) 0.0166(8) Uani 1 1 d . . . C7 C 0.6271(4) 1.3328(4) 0.1804(3) 0.0173(8) Uani 1 1 d . . . H7 H 0.6341 1.3511 0.1080 0.021 Uiso 1 1 calc R . . C8 C 0.6205(4) 1.5696(4) 0.1708(3) 0.0184(9) Uani 1 1 d . . . C9 C 0.9173(5) 0.8434(4) 0.0607(3) 0.0207(9) Uani 1 1 d . . . H9 H 0.8812 0.9233 0.0160 0.025 Uiso 1 1 calc R . . C10 C 1.0666(5) 0.7674(4) 0.0566(3) 0.0191(9) Uani 1 1 d . . . H10 H 1.1513 0.7846 0.0094 0.023 Uiso 1 1 calc R . . C11 C 0.9220(5) 0.6748(4) 0.1850(3) 0.0198(9) Uani 1 1 d . . . H11 H 0.8919 0.6155 0.2425 0.024 Uiso 1 1 calc R . . C12 C 1.2068(5) 0.5481(4) 0.1617(4) 0.0250(10) Uani 1 1 d . . . H12A H 1.2812 0.5820 0.1777 0.030 Uiso 1 1 calc R . . H12B H 1.2552 0.5056 0.1014 0.030 Uiso 1 1 calc R . . C13 C 1.1657(4) 0.4478(4) 0.2532(3) 0.0188(9) Uani 1 1 d . . . C14 C 1.1814(5) 0.4528(4) 0.3540(3) 0.0219(9) Uani 1 1 d . . . C15 C 1.1531(5) 0.3539(4) 0.4360(3) 0.0253(10) Uani 1 1 d . . . H15 H 1.1673 0.3552 0.5023 0.030 Uiso 1 1 calc R . . C16 C 1.1041(5) 0.2524(4) 0.4230(3) 0.0246(10) Uani 1 1 d . . . C17 C 1.0760(4) 0.2540(4) 0.3243(3) 0.0196(9) Uani 1 1 d . . . C18 C 1.1084(4) 0.3511(4) 0.2386(3) 0.0195(9) Uani 1 1 d . . . C19 C 1.0149(5) 0.1509(4) 0.3086(4) 0.0246(10) Uani 1 1 d . . . H19A H 0.9656 0.1123 0.3754 0.030 Uiso 1 1 calc R . . H19B H 0.9372 0.1923 0.2633 0.030 Uiso 1 1 calc R . . C20 C 1.1226(5) -0.0443(4) 0.2121(3) 0.0231(9) Uani 1 1 d . . . H20 H 1.0296 -0.0501 0.2020 0.028 Uiso 1 1 calc R . . C21 C 1.2671(5) -0.1220(4) 0.1808(3) 0.0211(9) Uani 1 1 d . . . H21 H 1.2905 -0.1912 0.1449 0.025 Uiso 1 1 calc R . . C22 C 1.2918(5) 0.0180(4) 0.2585(3) 0.0172(8) Uani 1 1 d . . . H22 H 1.3348 0.0647 0.2867 0.021 Uiso 1 1 calc R . . C23 C 1.2221(5) 0.5657(4) 0.3755(4) 0.0316(11) Uani 1 1 d . . . H23A H 1.2185 0.5555 0.4494 0.047 Uiso 1 1 calc R . . H23B H 1.1492 0.6484 0.3513 0.047 Uiso 1 1 calc R . . H23C H 1.3246 0.5648 0.3396 0.047 Uiso 1 1 calc R . . C24 C 1.0837(6) 0.1444(5) 0.5153(4) 0.0362(12) Uani 1 1 d . . . H24A H 1.1208 0.1550 0.5729 0.054 Uiso 1 1 calc R . . H24B H 1.1416 0.0595 0.4966 0.054 Uiso 1 1 calc R . . H24C H 0.9759 0.1500 0.5349 0.054 Uiso 1 1 calc R . . C25 C 1.0765(5) 0.3512(4) 0.1322(3) 0.0276(10) Uani 1 1 d . . . H25A H 0.9666 0.3766 0.1337 0.041 Uiso 1 1 calc R . . H25B H 1.1234 0.2639 0.1156 0.041 Uiso 1 1 calc R . . H25C H 1.1194 0.4131 0.0800 0.041 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 Cu1 0.0150(3) 0.0095(2) 0.0227(3) -0.00664(19) -0.00184(19) -0.00358(18) Br1 0.0685(4) 0.0332(3) 0.0183(2) -0.00140(19) -0.0086(2) -0.0272(3) N1 0.0186(17) 0.0130(16) 0.0266(19) -0.0049(14) -0.0052(15) -0.0063(14) N2 0.0154(17) 0.0150(16) 0.0257(19) -0.0056(14) -0.0003(14) -0.0047(14) N3 0.0163(17) 0.0131(16) 0.0233(19) -0.0048(14) -0.0011(14) -0.0045(13) N4 0.0199(18) 0.0112(15) 0.0176(17) -0.0031(13) -0.0024(14) -0.0064(13) O1 0.0221(15) 0.0132(13) 0.0272(16) -0.0085(12) -0.0009(12) -0.0085(11) O2 0.0300(17) 0.0202(15) 0.0205(16) -0.0084(12) -0.0032(13) -0.0106(13) O3 0.0253(15) 0.0096(13) 0.0205(15) -0.0070(11) 0.0008(12) -0.0060(11) O4 0.065(2) 0.0208(16) 0.0177(17) -0.0057(13) 0.0012(16) -0.0178(16) O5 0.0290(18) 0.0136(15) 0.0198(16) -0.0013(12) -0.0086(13) -0.0036(13) C1 0.0081(18) 0.0172(19) 0.023(2) -0.0079(16) 0.0003(15) -0.0045(15) C2 0.0152(19) 0.0126(18) 0.024(2) -0.0064(16) -0.0024(16) -0.0066(15) C3 0.019(2) 0.0127(19) 0.024(2) -0.0023(16) -0.0020(17) -0.0060(16) C4 0.025(2) 0.0170(19) 0.014(2) -0.0038(16) -0.0019(16) -0.0071(17) C5 0.021(2) 0.0140(19) 0.022(2) -0.0069(16) -0.0036(17) -0.0059(16) C6 0.0137(19) 0.0113(18) 0.024(2) -0.0050(16) -0.0004(16) -0.0036(15) C7 0.013(2) 0.018(2) 0.021(2) -0.0064(17) 0.0006(16) -0.0057(16) C8 0.0139(19) 0.0120(19) 0.029(2) -0.0039(17) -0.0022(17) -0.0042(15) C9 0.028(2) 0.0129(19) 0.023(2) -0.0015(16) -0.0086(18) -0.0070(17) C10 0.022(2) 0.020(2) 0.017(2) -0.0030(17) -0.0019(17) -0.0100(17) C11 0.019(2) 0.016(2) 0.023(2) -0.0037(17) -0.0004(17) -0.0058(16) C12 0.013(2) 0.015(2) 0.043(3) -0.0054(19) -0.0008(19) -0.0006(16) C13 0.0106(18) 0.0125(19) 0.028(2) -0.0035(17) 0.0012(16) 0.0005(15) C14 0.015(2) 0.017(2) 0.032(2) -0.0073(18) -0.0031(18) -0.0020(16) C15 0.030(2) 0.022(2) 0.023(2) -0.0066(18) -0.0049(19) -0.0047(19) C16 0.023(2) 0.020(2) 0.025(2) -0.0047(18) 0.0043(18) -0.0054(18) C17 0.0114(19) 0.0154(19) 0.027(2) -0.0097(17) 0.0040(16) 0.0013(16) C18 0.0107(19) 0.0160(19) 0.027(2) -0.0072(17) 0.0001(16) 0.0023(15) C19 0.017(2) 0.019(2) 0.037(3) -0.0109(19) 0.0031(18) -0.0057(17) C20 0.024(2) 0.022(2) 0.028(2) -0.0067(18) -0.0041(18) -0.0114(18) C21 0.024(2) 0.015(2) 0.027(2) -0.0068(17) -0.0025(18) -0.0090(17) C22 0.024(2) 0.0109(18) 0.019(2) -0.0027(16) -0.0043(17) -0.0068(16) C23 0.028(2) 0.027(2) 0.046(3) -0.018(2) 0.003(2) -0.013(2) C24 0.044(3) 0.027(3) 0.029(3) 0.000(2) 0.001(2) -0.008(2) C25 0.026(2) 0.024(2) 0.031(3) -0.0065(19) -0.0023(19) -0.0062(19) _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 Cu1 N1 1.957(3) . ? Cu1 N4 1.968(3) 1_465 ? Cu1 O1 1.988(3) . ? Cu1 O3 2.053(3) 1_545 ? Cu1 O5 2.221(3) . ? Br1 C4 1.900(4) . ? N1 C11 1.312(5) . ? N1 C9 1.379(5) . ? N2 C11 1.342(5) . ? N2 C10 1.371(5) . ? N2 C12 1.480(5) . ? N3 C22 1.329(5) . ? N3 C20 1.369(5) . ? N3 C19 1.486(5) . ? N4 C22 1.317(5) . ? N4 C21 1.375(5) . ? N4 Cu1 1.968(3) 1_645 ? O1 C1 1.270(5) . ? O2 C1 1.237(5) . ? O3 C8 1.272(5) . ? O3 Cu1 2.053(3) 1_565 ? O4 C8 1.237(5) . ? O5 H5C 0.89(4) . ? O5 H5D 0.77(5) . ? C1 C2 1.525(5) . ? C2 C7 1.382(5) . ? C2 C3 1.391(5) . ? C3 C4 1.388(5) . ? C3 H3 0.9300 . ? C4 C5 1.384(5) . ? C5 C6 1.382(6) . ? C5 H5 0.9300 . ? C6 C7 1.396(5) . ? C6 C8 1.525(5) . ? C7 H7 0.9300 . ? C9 C10 1.350(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.499(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.402(5) . ? C13 C14 1.405(6) . ? C14 C15 1.383(6) . ? C14 C23 1.511(6) . ? C15 C16 1.392(6) . ? C15 H15 0.9300 . ? C16 C17 1.399(6) . ? C16 C24 1.507(6) . ? C17 C18 1.408(6) . ? C17 C19 1.496(5) . ? C18 C25 1.520(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.356(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N4 178.22(13) . 1_465 ? N1 Cu1 O1 91.03(12) . . ? N4 Cu1 O1 88.51(12) 1_465 . ? N1 Cu1 O3 90.38(12) . 1_545 ? N4 Cu1 O3 91.09(12) 1_465 1_545 ? O1 Cu1 O3 139.15(11) . 1_545 ? N1 Cu1 O5 85.82(13) . . ? N4 Cu1 O5 93.08(13) 1_465 . ? O1 Cu1 O5 127.10(11) . . ? O3 Cu1 O5 93.72(11) 1_545 . ? C11 N1 C9 106.0(3) . . ? C11 N1 Cu1 127.9(3) . . ? C9 N1 Cu1 126.0(3) . . ? C11 N2 C10 107.2(3) . . ? C11 N2 C12 126.6(3) . . ? C10 N2 C12 126.3(3) . . ? C22 N3 C20 107.1(3) . . ? C22 N3 C19 126.4(3) . . ? C20 N3 C19 126.5(3) . . ? C22 N4 C21 105.5(3) . . ? C22 N4 Cu1 127.6(3) . 1_645 ? C21 N4 Cu1 126.7(3) . 1_645 ? C1 O1 Cu1 121.1(3) . . ? C8 O3 Cu1 127.8(3) . 1_565 ? Cu1 O5 H5C 89(3) . . ? Cu1 O5 H5D 127(4) . . ? H5C O5 H5D 112(4) . . ? O2 C1 O1 126.4(4) . . ? O2 C1 C2 118.5(3) . . ? O1 C1 C2 115.1(3) . . ? C7 C2 C3 119.5(3) . . ? C7 C2 C1 120.8(4) . . ? C3 C2 C1 119.7(3) . . ? C4 C3 C2 119.0(4) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 121.7(4) . . ? C5 C4 Br1 119.4(3) . . ? C3 C4 Br1 118.9(3) . . ? C6 C5 C4 119.2(4) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 119.5(4) . . ? C5 C6 C8 120.2(3) . . ? C7 C6 C8 120.2(4) . . ? C2 C7 C6 121.0(4) . . ? C2 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? O4 C8 O3 127.0(4) . . ? O4 C8 C6 118.0(3) . . ? O3 C8 C6 114.9(4) . . ? C10 C9 N1 109.1(3) . . ? C10 C9 H9 125.4 . . ? N1 C9 H9 125.4 . . ? C9 C10 N2 106.4(4) . . ? C9 C10 H10 126.8 . . ? N2 C10 H10 126.8 . . ? N1 C11 N2 111.2(4) . . ? N1 C11 H11 124.4 . . ? N2 C11 H11 124.4 . . ? N2 C12 C13 111.7(3) . . ? N2 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N2 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C18 C13 C14 120.1(4) . . ? C18 C13 C12 120.1(4) . . ? C14 C13 C12 119.8(4) . . ? C15 C14 C13 118.8(4) . . ? C15 C14 C23 119.3(4) . . ? C13 C14 C23 121.9(4) . . ? C14 C15 C16 122.3(4) . . ? C14 C15 H15 118.8 . . ? C16 C15 H15 118.8 . . ? C15 C16 C17 118.7(4) . . ? C15 C16 C24 119.0(4) . . ? C17 C16 C24 122.2(4) . . ? C16 C17 C18 120.1(4) . . ? C16 C17 C19 120.3(4) . . ? C18 C17 C19 119.6(4) . . ? C13 C18 C17 119.7(4) . . ? C13 C18 C25 121.1(4) . . ? C17 C18 C25 119.2(4) . . ? N3 C19 C17 111.5(3) . . ? N3 C19 H19A 109.3 . . ? C17 C19 H19A 109.3 . . ? N3 C19 H19B 109.3 . . ? C17 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? C21 C20 N3 106.4(4) . . ? C21 C20 H20 126.8 . . ? N3 C20 H20 126.8 . . ? C20 C21 N4 109.1(4) . . ? C20 C21 H21 125.5 . . ? N4 C21 H21 125.5 . . ? N4 C22 N3 111.9(3) . . ? N4 C22 H22 124.1 . . ? N3 C22 H22 124.1 . . ? C14 C23 H23A 109.5 . . ? C14 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C14 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C16 C24 H24A 109.5 . . ? C16 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C16 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C18 C25 H25A 109.5 . . ? C18 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C18 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.105 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 939333' ####################################################################### # # 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_y99_NiBripBitmb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H25 Br N4 Ni O5' _chemical_formula_weight 600.11 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 9.320(3) _cell_length_b 10.402(3) _cell_length_c 13.855(5) _cell_angle_alpha 76.135(6) _cell_angle_beta 75.941(6) _cell_angle_gamma 71.167(6) _cell_volume 1214.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 922 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 21.51 _exptl_crystal_description plates _exptl_crystal_colour 'PALE GREEN' _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 2.490 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8856 _exptl_absorpt_correction_T_max 0.9519 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFARCTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10166 _diffrn_reflns_av_R_equivalents 0.0710 _diffrn_reflns_av_sigmaI/netI 0.1313 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5211 _reflns_number_gt 3501 _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 ORTEP _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5211 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0859 _refine_ls_wR_factor_ref 0.1524 _refine_ls_wR_factor_gt 0.1358 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 0.39492(9) 1.14676(8) 0.34667(6) 0.0137(2) Uani 1 1 d . . . Br1 Br 0.43170(10) 0.75211(8) -0.04259(5) 0.0382(3) Uani 1 1 d . . . O1 O 0.3797(5) 0.9297(4) 0.3835(3) 0.0178(10) Uani 1 1 d . . . O2 O 0.3762(5) 1.0549(4) 0.2310(3) 0.0183(10) Uani 1 1 d . . . O3 O 0.3661(6) 0.4363(4) 0.4216(3) 0.0291(12) Uani 1 1 d . . . O4 O 0.3994(5) 0.3470(4) 0.2823(3) 0.0170(10) Uani 1 1 d . . . O5 O 0.4004(5) 1.1735(5) 0.4884(3) 0.0188(11) Uani 1 1 d . . . H5C H 0.394(9) 1.259(8) 0.470(6) 0.050 Uiso 1 1 d . . . H5D H 0.456(9) 1.140(8) 0.527(6) 0.050 Uiso 1 1 d . . . N1 N 0.6278(6) 1.0781(5) 0.3068(4) 0.0166(12) Uani 1 1 d . . . N2 N 0.8629(6) 0.9625(5) 0.2411(4) 0.0214(13) Uani 1 1 d . . . N3 N 0.9227(6) 0.3343(5) 0.3756(4) 0.0192(12) Uani 1 1 d . . . N4 N 1.1621(6) 0.2111(5) 0.3801(4) 0.0173(12) Uani 1 1 d . . . C1 C 0.3797(6) 0.9427(6) 0.2896(5) 0.0129(13) Uani 1 1 d . . . C2 C 0.3856(7) 0.8206(6) 0.2476(4) 0.0150(13) Uani 1 1 d . . . C3 C 0.3825(7) 0.6926(6) 0.3051(4) 0.0142(13) Uani 1 1 d . . . H3 H 0.3791 0.6795 0.3743 0.017 Uiso 1 1 calc R . . C4 C 0.3843(7) 0.5833(6) 0.2638(4) 0.0123(13) Uani 1 1 d . . . C5 C 0.3935(7) 0.6029(6) 0.1597(5) 0.0188(15) Uani 1 1 d . . . H5A H 0.3932 0.5319 0.1299 0.023 Uiso 1 1 calc R . . C6 C 0.4032(7) 0.7288(6) 0.1008(4) 0.0185(15) Uani 1 1 d . . . C7 C 0.3973(7) 0.8380(6) 0.1426(5) 0.0181(14) Uani 1 1 d . . . H7 H 0.4011 0.9225 0.1018 0.022 Uiso 1 1 calc R . . C8 C 0.3822(7) 0.4444(6) 0.3280(5) 0.0179(14) Uani 1 1 d . . . C9 C 0.7363(8) 1.1146(7) 0.3366(5) 0.0261(16) Uani 1 1 d . . . H9 H 0.7136 1.1788 0.3786 0.031 Uiso 1 1 calc R . . C10 C 0.8810(8) 1.0459(7) 0.2973(5) 0.0244(16) Uani 1 1 d . . . H10 H 0.9731 1.0538 0.3065 0.029 Uiso 1 1 calc R . . C11 C 0.7105(7) 0.9848(7) 0.2487(5) 0.0246(16) Uani 1 1 d . . . H11 H 0.6678 0.9403 0.2171 0.030 Uiso 1 1 calc R . . C12 C 0.9859(7) 0.8584(7) 0.1898(5) 0.0278(17) Uani 1 1 d . . . H12A H 1.0678 0.8180 0.2290 0.033 Uiso 1 1 calc R . . H12B H 1.0286 0.9028 0.1241 0.033 Uiso 1 1 calc R . . C13 C 0.9270(7) 0.7460(7) 0.1763(6) 0.0259(16) Uani 1 1 d . . . C14 C 0.8936(7) 0.6479(7) 0.2614(5) 0.0229(16) Uani 1 1 d . . . C15 C 0.8354(7) 0.5449(7) 0.2510(5) 0.0231(16) Uani 1 1 d . . . C16 C 0.8197(8) 0.5332(7) 0.1561(5) 0.0263(16) Uani 1 1 d . . . C17 C 0.8479(8) 0.6344(7) 0.0744(6) 0.0298(18) Uani 1 1 d . . . H17 H 0.8321 0.6300 0.0117 0.036 Uiso 1 1 calc R . . C18 C 0.8989(8) 0.7421(7) 0.0827(5) 0.0256(16) Uani 1 1 d . . . C19 C 0.7877(8) 0.4448(7) 0.3426(5) 0.0301(17) Uani 1 1 d . . . H19A H 0.7321 0.4947 0.3976 0.036 Uiso 1 1 calc R . . H19B H 0.7187 0.4034 0.3268 0.036 Uiso 1 1 calc R . . C20 C 0.9185(8) 0.2336(7) 0.4587(5) 0.0266(17) Uani 1 1 d . . . H20 H 0.8318 0.2196 0.5049 0.032 Uiso 1 1 calc R . . C21 C 1.0653(7) 0.1587(7) 0.4601(5) 0.0236(16) Uani 1 1 d . . . H21 H 1.0972 0.0818 0.5087 0.028 Uiso 1 1 calc R . . C22 C 1.0704(7) 0.3172(6) 0.3302(5) 0.0180(14) Uani 1 1 d . . . H22 H 1.1037 0.3728 0.2712 0.022 Uiso 1 1 calc R . . C23 C 0.9246(8) 0.6519(7) 0.3632(5) 0.0335(19) Uani 1 1 d . . . H23A H 0.8945 0.5789 0.4128 0.050 Uiso 1 1 calc R . . H23B H 0.8664 0.7391 0.3829 0.050 Uiso 1 1 calc R . . H23C H 1.0325 0.6401 0.3581 0.050 Uiso 1 1 calc R . . C24 C 0.7764(8) 0.4159(7) 0.1370(5) 0.0316(18) Uani 1 1 d . . . H24A H 0.7792 0.4257 0.0659 0.047 Uiso 1 1 calc R . . H24B H 0.6743 0.4167 0.1731 0.047 Uiso 1 1 calc R . . H24C H 0.8480 0.3302 0.1596 0.047 Uiso 1 1 calc R . . C25 C 0.9190(9) 0.8540(8) -0.0074(6) 0.042(2) Uani 1 1 d . . . H25A H 0.8598 0.9423 0.0100 0.063 Uiso 1 1 calc R . . H25B H 0.8841 0.8395 -0.0627 0.063 Uiso 1 1 calc R . . H25C H 1.0259 0.8513 -0.0270 0.063 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 0.0159(5) 0.0072(4) 0.0177(5) -0.0028(3) -0.0032(3) -0.0020(3) Br1 0.0752(7) 0.0294(5) 0.0152(4) -0.0015(3) -0.0087(4) -0.0232(4) O1 0.025(3) 0.015(2) 0.016(2) -0.0047(18) -0.0076(19) -0.005(2) O2 0.027(3) 0.007(2) 0.018(2) -0.0020(18) -0.002(2) -0.0032(19) O3 0.055(3) 0.012(2) 0.021(3) -0.003(2) -0.004(2) -0.012(2) O4 0.024(3) 0.010(2) 0.016(2) -0.0042(18) -0.0013(19) -0.0036(19) O5 0.031(3) 0.011(2) 0.015(2) 0.0000(19) -0.006(2) -0.007(2) N1 0.020(3) 0.010(3) 0.019(3) -0.002(2) -0.006(2) -0.003(2) N2 0.022(3) 0.018(3) 0.023(3) -0.010(2) 0.003(2) -0.006(3) N3 0.014(3) 0.018(3) 0.025(3) -0.010(2) -0.001(2) -0.001(2) N4 0.019(3) 0.014(3) 0.018(3) -0.003(2) 0.000(2) -0.005(2) C1 0.006(3) 0.010(3) 0.025(4) -0.005(3) -0.002(3) -0.003(2) C2 0.013(3) 0.017(3) 0.018(3) -0.008(3) 0.001(3) -0.006(3) C3 0.017(3) 0.013(3) 0.013(3) -0.005(3) 0.000(3) -0.005(3) C4 0.013(3) 0.007(3) 0.016(3) -0.001(2) -0.003(3) -0.002(3) C5 0.019(4) 0.016(3) 0.026(4) -0.012(3) -0.002(3) -0.005(3) C6 0.024(4) 0.020(4) 0.012(3) -0.003(3) -0.002(3) -0.007(3) C7 0.019(4) 0.018(3) 0.019(3) -0.001(3) -0.002(3) -0.010(3) C8 0.019(4) 0.015(3) 0.018(4) -0.001(3) -0.002(3) -0.005(3) C9 0.032(4) 0.019(4) 0.034(4) -0.013(3) -0.005(3) -0.012(3) C10 0.023(4) 0.026(4) 0.029(4) -0.004(3) -0.008(3) -0.012(3) C11 0.017(4) 0.026(4) 0.031(4) -0.007(3) -0.006(3) -0.003(3) C12 0.017(4) 0.026(4) 0.035(4) -0.011(3) 0.006(3) -0.002(3) C13 0.010(4) 0.022(4) 0.044(5) -0.016(3) 0.000(3) 0.002(3) C14 0.014(4) 0.022(4) 0.031(4) -0.013(3) -0.006(3) 0.006(3) C15 0.015(4) 0.018(4) 0.033(4) -0.006(3) -0.005(3) 0.001(3) C16 0.018(4) 0.016(4) 0.040(4) -0.010(3) -0.006(3) 0.004(3) C17 0.028(4) 0.027(4) 0.036(4) -0.013(3) -0.015(3) 0.002(3) C18 0.025(4) 0.019(4) 0.026(4) -0.007(3) -0.002(3) 0.002(3) C19 0.030(4) 0.029(4) 0.032(4) -0.010(3) -0.001(3) -0.007(3) C20 0.023(4) 0.031(4) 0.024(4) -0.004(3) 0.004(3) -0.012(3) C21 0.021(4) 0.028(4) 0.021(4) 0.000(3) -0.003(3) -0.010(3) C22 0.016(4) 0.014(3) 0.023(4) -0.004(3) 0.000(3) -0.005(3) C23 0.023(4) 0.029(4) 0.047(5) -0.018(4) 0.003(4) -0.003(3) C24 0.026(4) 0.034(4) 0.040(5) -0.012(4) -0.010(3) -0.007(4) C25 0.048(5) 0.037(5) 0.039(5) -0.011(4) -0.007(4) -0.006(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 Ni1 N4 2.024(5) 1_465 ? Ni1 N1 2.033(5) . ? Ni1 O5 2.063(4) . ? Ni1 O4 2.070(4) 1_565 ? Ni1 O2 2.119(4) . ? Ni1 O1 2.235(4) . ? Br1 C6 1.906(6) . ? O1 C1 1.275(7) . ? O2 C1 1.248(7) . ? O3 C8 1.255(7) . ? O4 C8 1.268(7) . ? O4 Ni1 2.070(4) 1_545 ? O5 H5C 0.86(8) . ? O5 H5D 0.78(8) . ? N1 C11 1.332(8) . ? N1 C9 1.365(8) . ? N2 C11 1.345(8) . ? N2 C10 1.367(8) . ? N2 C12 1.471(8) . ? N3 C22 1.340(7) . ? N3 C20 1.360(8) . ? N3 C19 1.486(8) . ? N4 C22 1.318(7) . ? N4 C21 1.372(7) . ? N4 Ni1 2.024(5) 1_645 ? C1 C2 1.500(8) . ? C2 C3 1.383(8) . ? C2 C7 1.404(8) . ? C3 C4 1.384(8) . ? C3 H3 0.9300 . ? C4 C5 1.392(8) . ? C4 C8 1.507(8) . ? C5 C6 1.384(8) . ? C5 H5A 0.9300 . ? C6 C7 1.375(8) . ? C7 H7 0.9300 . ? C9 C10 1.354(9) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.508(9) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.396(9) . ? C13 C14 1.407(9) . ? C14 C15 1.396(9) . ? C14 C23 1.519(9) . ? C15 C16 1.395(9) . ? C15 C19 1.511(9) . ? C16 C17 1.387(9) . ? C16 C24 1.499(9) . ? C17 C18 1.387(9) . ? C17 H17 0.9300 . ? C18 C25 1.510(9) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.340(9) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ni1 N1 176.9(2) 1_465 . ? N4 Ni1 O5 88.41(19) 1_465 . ? N1 Ni1 O5 94.5(2) . . ? N4 Ni1 O4 89.94(18) 1_465 1_565 ? N1 Ni1 O4 90.75(18) . 1_565 ? O5 Ni1 O4 92.72(17) . 1_565 ? N4 Ni1 O2 88.78(18) 1_465 . ? N1 Ni1 O2 88.16(18) . . ? O5 Ni1 O2 160.22(16) . . ? O4 Ni1 O2 106.85(16) 1_565 . ? N4 Ni1 O1 88.35(18) 1_465 . ? N1 Ni1 O1 90.33(17) . . ? O5 Ni1 O1 99.66(16) . . ? O4 Ni1 O1 167.45(16) 1_565 . ? O2 Ni1 O1 60.69(15) . . ? C1 O1 Ni1 85.8(3) . . ? C1 O2 Ni1 91.7(4) . . ? C8 O4 Ni1 127.2(4) . 1_545 ? Ni1 O5 H5C 94(5) . . ? Ni1 O5 H5D 136(6) . . ? H5C O5 H5D 110(7) . . ? C11 N1 C9 103.8(5) . . ? C11 N1 Ni1 128.7(4) . . ? C9 N1 Ni1 127.5(4) . . ? C11 N2 C10 107.1(5) . . ? C11 N2 C12 126.1(6) . . ? C10 N2 C12 126.6(6) . . ? C22 N3 C20 107.7(5) . . ? C22 N3 C19 126.3(5) . . ? C20 N3 C19 125.9(5) . . ? C22 N4 C21 104.9(5) . . ? C22 N4 Ni1 126.7(4) . 1_645 ? C21 N4 Ni1 128.4(4) . 1_645 ? O2 C1 O1 121.6(5) . . ? O2 C1 C2 118.7(5) . . ? O1 C1 C2 119.7(5) . . ? C3 C2 C7 118.4(6) . . ? C3 C2 C1 124.4(5) . . ? C7 C2 C1 117.2(5) . . ? C2 C3 C4 122.7(6) . . ? C2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? C3 C4 C5 118.2(5) . . ? C3 C4 C8 121.6(5) . . ? C5 C4 C8 120.1(5) . . ? C6 C5 C4 119.6(6) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C7 C6 C5 121.9(6) . . ? C7 C6 Br1 118.2(5) . . ? C5 C6 Br1 119.9(5) . . ? C6 C7 C2 119.2(6) . . ? C6 C7 H7 120.4 . . ? C2 C7 H7 120.4 . . ? O3 C8 O4 126.4(6) . . ? O3 C8 C4 116.5(5) . . ? O4 C8 C4 117.1(5) . . ? C10 C9 N1 111.6(6) . . ? C10 C9 H9 124.2 . . ? N1 C9 H9 124.2 . . ? C9 C10 N2 105.4(6) . . ? C9 C10 H10 127.3 . . ? N2 C10 H10 127.3 . . ? N1 C11 N2 112.1(6) . . ? N1 C11 H11 123.9 . . ? N2 C11 H11 123.9 . . ? N2 C12 C13 111.7(5) . . ? N2 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N2 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C18 C13 C14 120.2(6) . . ? C18 C13 C12 121.2(7) . . ? C14 C13 C12 118.6(6) . . ? C15 C14 C13 119.5(6) . . ? C15 C14 C23 120.3(6) . . ? C13 C14 C23 120.2(6) . . ? C16 C15 C14 120.6(6) . . ? C16 C15 C19 119.0(6) . . ? C14 C15 C19 120.4(6) . . ? C17 C16 C15 118.4(6) . . ? C17 C16 C24 117.9(7) . . ? C15 C16 C24 123.7(6) . . ? C16 C17 C18 122.5(7) . . ? C16 C17 H17 118.8 . . ? C18 C17 H17 118.8 . . ? C17 C18 C13 118.5(6) . . ? C17 C18 C25 120.2(7) . . ? C13 C18 C25 121.2(6) . . ? N3 C19 C15 111.8(5) . . ? N3 C19 H19A 109.3 . . ? C15 C19 H19A 109.3 . . ? N3 C19 H19B 109.3 . . ? C15 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C21 C20 N3 105.8(6) . . ? C21 C20 H20 127.1 . . ? N3 C20 H20 127.1 . . ? C20 C21 N4 110.6(6) . . ? C20 C21 H21 124.7 . . ? N4 C21 H21 124.7 . . ? N4 C22 N3 111.1(6) . . ? N4 C22 H22 124.5 . . ? N3 C22 H22 124.5 . . ? C14 C23 H23A 109.5 . . ? C14 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C14 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C16 C24 H24A 109.5 . . ? C16 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C16 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C18 C25 H25A 109.5 . . ? C18 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C18 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.004 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.134 _database_code_depnum_ccdc_archive 'CCDC 939334'