Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 186 _publ_contact_author ; Prof Rita Delgado ITQB - Instituto de Tecnologia Quimica e Biologica, UNL Apartado 127 2781-901 Oeiras PORTUGAL ; _publ_contact_letter ; ? ; _publ_requested_journal ' Dalton Transactions ' _publ_requested_coeditor_name ' ?' _publ_section_title ; X-ray diffraction and molecular mechanics studies of 12-,13-, and 14-membered tetraazamacrocycles containing pyridine:effect of the macrocyclic cavity size in the selectivity of the metal ion ; loop_ _publ_author_name #_publ_author_address 'V. Felix' # a) 'J. Costa' # b);c) 'R. Delgado' # b);d) 'M. G.B. Drew' # e) 'M. T. Duarte' # d); f) 'C. Resende' # f) #; a)Dep. de Química, Universidade de Aveiro, 3810-193 Aveiro, Portugal #b)Instituto de Tecnologia Química e Biológica, #UNL, Apartado 127, 2781-901 Oeiras, Portugal #c)Faculdade de Farmácia de Lisboa, Av. das Forças Armadas, 1600 Lisboa, #Portugal #d)Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisboa, Portugal #e)Dep. of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, UK #f)Centro de Química Estrutural, Av. Rovisco Pais, 1049-001 Lisboa, Portugal #; #-------------------------- data section of block --------------------------- #======BEGIN data_1 _database_code_CSD 154180 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 Br Cl Cu N4 O4' _chemical_formula_weight 449.19 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' 'Cl' 'Cl' 0.1484 0.1585 '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 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.950(11) _cell_length_b 22.307(27) _cell_length_c 18.298(23) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3245(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.839 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1800 _exptl_absorpt_coefficient_mu 3.995 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 MAR research image plate system _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9223 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.04 _reflns_number_total 5383 _reflns_number_gt 3523 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w==1/[\s^2^(Fo^2^)+(0.1357P)^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 SHELXL _refine_ls_extinction_coef 0.0011(4) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5383 _refine_ls_number_parameters 397 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1203 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.2129 _refine_ls_wR_factor_gt 0.1862 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 CuA Cu 0.59127(15) 0.40292(5) 0.13218(7) 0.0458(4) Uani 1 d . . . BrA Br 0.36642(16) 0.47238(6) 0.14831(7) 0.0684(4) Uani 1 d . . . N1A N 0.6309(12) 0.3784(4) 0.2390(5) 0.055(2) Uani 1 d . . . H1A H 0.5404 0.3902 0.2659 0.066 Uiso 1 calc R . . C2A C 0.6499(17) 0.3125(5) 0.2464(7) 0.067(3) Uani 1 d . . . H2A1 H 0.5507 0.2962 0.2700 0.081 Uiso 1 calc R . . H2A2 H 0.7462 0.3039 0.2772 0.081 Uiso 1 calc R . . C3A C 0.6732(14) 0.2825(5) 0.1737(7) 0.053(3) Uani 1 d . . . N4A N 0.6470(10) 0.3184(4) 0.1141(5) 0.045(2) Uani 1 d . . . C5A C 0.6659(13) 0.3000(5) 0.0470(7) 0.055(3) Uani 1 d . . . C6A C 0.6406(17) 0.3457(6) -0.0112(6) 0.065(3) Uani 1 d . . . H6A1 H 0.7347 0.3445 -0.0449 0.078 Uiso 1 calc R . . H6A2 H 0.5392 0.3363 -0.0383 0.078 Uiso 1 calc R . . N7A N 0.6260(12) 0.4066(4) 0.0198(5) 0.056(3) Uani 1 d . . . H7A H 0.5364 0.4254 -0.0010 0.067 Uiso 1 calc R . . C8A C 0.7801(19) 0.4437(5) 0.0081(8) 0.071(4) Uani 1 d . . . H8A1 H 0.7509 0.4859 0.0094 0.085 Uiso 1 calc R . . H8A2 H 0.8280 0.4349 -0.0395 0.085 Uiso 1 calc R . . C9A C 0.9074(15) 0.4300(5) 0.0672(6) 0.059(3) Uani 1 d . . . H9A1 H 0.9383 0.3880 0.0653 0.070 Uiso 1 calc R . . H9A2 H 1.0082 0.4537 0.0595 0.070 Uiso 1 calc R . . N10A N 0.8353(11) 0.4439(4) 0.1372(5) 0.049(2) Uani 1 d . . . H10A H 0.8256 0.4843 0.1429 0.059 Uiso 1 calc R . . C11A C 0.9089(16) 0.4166(6) 0.2030(7) 0.067(3) Uani 1 d . . . H11A H 1.0053 0.4398 0.2188 0.081 Uiso 1 calc R . . H11B H 0.9469 0.3762 0.1919 0.081 Uiso 1 calc R . . C12A C 0.7810(17) 0.4145(6) 0.2627(7) 0.070(4) Uani 1 d . . . H12A H 0.7458 0.4549 0.2749 0.084 Uiso 1 calc R . . H12B H 0.8302 0.3966 0.3060 0.084 Uiso 1 calc R . . C13A C 0.7099(16) 0.2220(5) 0.1610(9) 0.071(4) Uani 1 d . . . H13A H 0.7242 0.1957 0.1998 0.085 Uiso 1 calc R . . C14A C 0.7245(16) 0.2022(5) 0.0900(10) 0.077(4) Uani 1 d . . . H14A H 0.7486 0.1620 0.0818 0.092 Uiso 1 calc R . . C15A C 0.7054(17) 0.2384(5) 0.0325(8) 0.072(4) Uani 1 d . . . H15A H 0.7173 0.2243 -0.0151 0.087 Uiso 1 calc R . . CuB Cu 0.41553(15) 0.59679(5) 0.39094(7) 0.0429(3) Uani 1 d . . . BrB Br 0.68964(15) 0.54865(6) 0.39480(8) 0.0635(4) Uani 1 d . . . N1B N 0.4068(13) 0.6401(4) 0.4907(5) 0.062(3) Uani 1 d . . . H1B H 0.5028 0.6311 0.5155 0.074 Uiso 1 calc R . . C2B C 0.4006(19) 0.7058(5) 0.4808(6) 0.070(4) Uani 1 d . . . H2B1 H 0.3166 0.7224 0.5135 0.084 Uiso 1 calc R . . H2B2 H 0.5086 0.7228 0.4941 0.084 Uiso 1 calc R . . C3B C 0.3598(14) 0.7232(5) 0.4052(7) 0.056(3) Uani 1 d . . . N4B N 0.3690(10) 0.6774(3) 0.3559(4) 0.0408(19) Uani 1 d . . . C5B C 0.3282(14) 0.6860(5) 0.2845(6) 0.052(3) Uani 1 d . . . C6B C 0.3356(17) 0.6290(5) 0.2409(7) 0.064(3) Uani 1 d . . . H6B1 H 0.2445 0.6283 0.2057 0.077 Uiso 1 calc R . . H6B2 H 0.4411 0.6270 0.2144 0.077 Uiso 1 calc R . . N7B N 0.3212(11) 0.5767(4) 0.2911(5) 0.055(2) Uani 1 d . . . H7B H 0.3760 0.5445 0.2719 0.067 Uiso 1 calc R . . C8B C 0.1448(16) 0.5608(6) 0.3079(8) 0.070(4) Uani 1 d . . . H8B1 H 0.0923 0.5438 0.2648 0.083 Uiso 1 calc R . . H8B2 H 0.0832 0.5968 0.3211 0.083 Uiso 1 calc R . . C9B C 0.1349(17) 0.5162(5) 0.3699(8) 0.073(4) Uani 1 d . . . H9B1 H 0.0187 0.5102 0.3843 0.088 Uiso 1 calc R . . H9B2 H 0.1811 0.4780 0.3546 0.088 Uiso 1 calc R . . N10B N 0.2335(12) 0.5407(4) 0.4322(6) 0.057(3) Uani 1 d . . . H10B H 0.2802 0.5106 0.4590 0.069 Uiso 1 calc R . . C11B C 0.1417(18) 0.5819(6) 0.4785(8) 0.079(4) Uani 1 d . . . H11C H 0.0553 0.5604 0.5052 0.094 Uiso 1 calc R . . H11D H 0.0872 0.6121 0.4485 0.094 Uiso 1 calc R . . C12B C 0.260(2) 0.6117(7) 0.5315(7) 0.082(4) Uani 1 d . . . H12C H 0.3018 0.5823 0.5660 0.098 Uiso 1 calc R . . H12D H 0.1999 0.6423 0.5587 0.098 Uiso 1 calc R . . C13B C 0.3226(14) 0.7803(5) 0.3797(7) 0.057(3) Uani 1 d . . . H13B H 0.3205 0.8127 0.4117 0.068 Uiso 1 calc R . . C14B C 0.2892(17) 0.7884(6) 0.3076(8) 0.072(4) Uani 1 d . . . H14B H 0.2653 0.8270 0.2914 0.087 Uiso 1 calc R . . C15B C 0.2889(17) 0.7421(6) 0.2566(8) 0.071(4) Uani 1 d . . . H15B H 0.2641 0.7483 0.2075 0.085 Uiso 1 calc R . . Cl1 Cl 0.7634(3) 0.66065(13) 0.62401(16) 0.0570(7) Uani 1 d D . . O111 O 0.663(3) 0.7137(7) 0.6146(13) 0.102(12) Uiso 0.40(2) d PD . . O121 O 0.9333(16) 0.6780(11) 0.6421(14) 0.120(12) Uiso 0.40(2) d PD . . O131 O 0.697(3) 0.6261(9) 0.6838(10) 0.098(10) Uiso 0.40(2) d PD . . O141 O 0.763(3) 0.6262(10) 0.5588(9) 0.099(10) Uiso 0.40(2) d PD . . O112 O 0.686(2) 0.7186(5) 0.6346(10) 0.089(7) Uiso 0.60(2) d PD . . O122 O 0.894(2) 0.6516(9) 0.6748(9) 0.155(11) Uiso 0.60(2) d PD . . O132 O 0.823(2) 0.6565(7) 0.5502(6) 0.090(6) Uiso 0.60(2) d PD . . O142 O 0.6323(16) 0.6156(6) 0.6328(10) 0.088(6) Uiso 0.60(2) d PD . . Cl2 Cl 0.8145(4) 0.62071(12) 0.11869(16) 0.0602(7) Uani 1 d . . . O21 O 0.825(2) 0.5789(5) 0.1762(7) 0.140(6) Uani 1 d . . . O22 O 0.6858(13) 0.6623(4) 0.1347(6) 0.085(3) Uani 1 d . . . O23 O 0.9692(15) 0.6547(6) 0.1097(8) 0.123(4) Uani 1 d . . . O24 O 0.7725(17) 0.5913(5) 0.0510(6) 0.109(4) Uani 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 CuA 0.0453(7) 0.0494(7) 0.0429(7) -0.0006(6) 0.0005(7) 0.0122(5) BrA 0.0598(8) 0.0783(8) 0.0671(9) -0.0162(6) -0.0088(6) 0.0316(6) N1A 0.050(6) 0.080(6) 0.036(5) -0.003(5) 0.004(4) 0.015(5) C2A 0.069(8) 0.069(8) 0.064(8) 0.014(6) 0.022(6) 0.018(6) C3A 0.045(6) 0.053(6) 0.063(8) 0.014(6) 0.006(5) 0.000(5) N4A 0.036(5) 0.050(5) 0.049(6) 0.002(4) 0.010(4) -0.001(3) C5A 0.039(6) 0.058(7) 0.069(9) -0.026(6) 0.003(5) 0.000(5) C6A 0.076(9) 0.090(9) 0.029(6) -0.021(6) 0.003(5) 0.008(6) N7A 0.061(6) 0.078(7) 0.029(5) 0.010(4) 0.002(4) 0.028(5) C8A 0.086(10) 0.056(7) 0.070(9) 0.010(6) 0.023(7) 0.015(6) C9A 0.064(8) 0.059(7) 0.053(7) 0.008(6) 0.009(6) -0.010(6) N10A 0.055(6) 0.048(5) 0.045(5) -0.001(4) -0.006(4) 0.004(4) C11A 0.057(8) 0.069(8) 0.075(9) -0.015(6) -0.022(7) 0.001(6) C12A 0.068(9) 0.075(9) 0.065(9) -0.017(7) -0.007(7) 0.010(6) C13A 0.056(8) 0.046(7) 0.111(12) 0.012(7) 0.003(7) -0.007(5) C14A 0.065(8) 0.033(6) 0.132(14) -0.018(8) -0.005(8) -0.004(5) C15A 0.069(9) 0.051(7) 0.097(11) -0.016(7) 0.002(7) -0.004(6) CuB 0.0362(7) 0.0462(7) 0.0464(8) 0.0002(5) -0.0015(5) 0.0078(4) BrB 0.0428(6) 0.0664(7) 0.0813(9) -0.0028(6) -0.0031(6) 0.0179(5) N1B 0.065(6) 0.061(6) 0.060(6) 0.011(5) 0.001(5) 0.019(5) C2B 0.106(10) 0.053(7) 0.051(7) -0.017(6) -0.024(7) 0.015(7) C3B 0.047(6) 0.053(7) 0.067(8) -0.007(6) 0.010(5) 0.011(5) N4B 0.043(5) 0.041(4) 0.038(5) 0.002(4) 0.007(3) 0.007(3) C5B 0.050(6) 0.066(7) 0.041(7) 0.009(5) 0.002(5) -0.005(5) C6B 0.073(9) 0.073(8) 0.047(7) -0.004(6) 0.000(6) 0.009(6) N7B 0.049(6) 0.052(5) 0.065(7) -0.013(5) 0.011(5) 0.007(4) C8B 0.055(8) 0.070(9) 0.083(10) -0.024(7) -0.011(6) -0.003(6) C9B 0.058(7) 0.051(7) 0.111(12) -0.004(7) -0.001(8) 0.004(5) N10B 0.050(6) 0.059(6) 0.064(6) 0.026(5) 0.014(5) 0.009(4) C11B 0.072(10) 0.084(10) 0.080(10) -0.001(8) 0.024(8) 0.013(7) C12B 0.101(12) 0.098(11) 0.046(8) 0.012(7) 0.030(7) 0.026(8) C13B 0.051(7) 0.053(7) 0.066(9) 0.002(6) 0.003(6) 0.007(5) C14B 0.074(9) 0.055(8) 0.088(11) 0.023(7) -0.001(7) 0.011(6) C15B 0.072(8) 0.070(8) 0.070(9) 0.028(7) 0.013(6) 0.016(6) Cl1 0.0495(16) 0.0728(18) 0.0487(17) 0.0052(14) -0.0034(12) 0.0061(11) Cl2 0.0699(19) 0.0506(15) 0.060(2) -0.0015(14) -0.0029(14) 0.0053(13) O21 0.226(18) 0.077(7) 0.117(10) 0.029(7) -0.050(11) -0.016(9) O22 0.090(7) 0.083(6) 0.080(6) -0.017(5) -0.009(6) 0.018(5) O23 0.076(8) 0.148(11) 0.146(12) -0.005(9) 0.022(7) -0.016(7) O24 0.127(10) 0.114(9) 0.086(8) -0.040(7) -0.007(7) 0.018(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 CuA N4A 1.965(9) . ? CuA N1A 2.054(9) . ? CuA N7A 2.077(9) . ? CuA N10A 2.146(9) . ? CuA BrA 2.384(3) . ? N1A C2A 1.484(14) . ? N1A C12A 1.503(16) . ? C2A C3A 1.500(17) . ? C3A N4A 1.370(14) . ? C3A C13A 1.398(16) . ? N4A C5A 1.302(14) . ? C5A C15A 1.433(16) . ? C5A C6A 1.489(17) . ? C6A N7A 1.475(14) . ? N7A C8A 1.494(17) . ? C8A C9A 1.512(18) . ? C9A N10A 1.437(15) . ? N10A C11A 1.471(15) . ? C11A C12A 1.493(18) . ? C13A C14A 1.38(2) . ? C14A C15A 1.34(2) . ? CuB N4B 1.945(8) . ? CuB N7B 2.026(10) . ? CuB N10B 2.058(9) . ? CuB N1B 2.067(10) . ? CuB BrB 2.430(3) . ? N1B C2B 1.479(14) . ? N1B C12B 1.523(17) . ? C2B C3B 1.473(16) . ? C3B N4B 1.363(13) . ? C3B C13B 1.390(15) . ? N4B C5B 1.361(13) . ? C5B C15B 1.387(16) . ? C5B C6B 1.501(16) . ? C6B N7B 1.490(15) . ? N7B C8B 1.479(16) . ? C8B C9B 1.510(19) . ? C9B N10B 1.487(17) . ? N10B C11B 1.447(15) . ? C11B C12B 1.51(2) . ? C13B C14B 1.357(18) . ? C14B C15B 1.392(19) . ? Cl1 O122 1.406(11) . ? Cl1 O141 1.420(11) . ? Cl1 O132 1.433(10) . ? Cl1 O111 1.437(10) . ? Cl1 O131 1.438(11) . ? Cl1 O112 1.444(9) . ? Cl1 O121 1.444(11) . ? Cl1 O142 1.457(10) . ? O121 O122 0.90(3) . ? O131 O142 1.09(2) . ? O131 O122 1.67(2) . ? O141 O132 0.84(2) . ? O141 O142 1.72(2) . ? Cl2 O21 1.408(12) . ? Cl2 O22 1.412(10) . ? Cl2 O24 1.441(11) . ? Cl2 O23 1.454(12) . ? 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 N4A CuA N1A 82.5(4) . . ? N4A CuA N7A 80.8(4) . . ? N1A CuA N7A 158.8(4) . . ? N4A CuA N10A 102.2(3) . . ? N1A CuA N10A 86.2(4) . . ? N7A CuA N10A 84.6(4) . . ? N4A CuA BrA 144.4(2) . . ? N1A CuA BrA 99.8(3) . . ? N7A CuA BrA 101.3(2) . . ? N10A CuA BrA 113.3(2) . . ? C2A N1A C12A 115.1(10) . . ? C2A N1A CuA 111.5(7) . . ? C12A N1A CuA 104.7(8) . . ? N1A C2A C3A 112.0(9) . . ? N4A C3A C13A 117.5(12) . . ? N4A C3A C2A 115.2(9) . . ? C13A C3A C2A 127.2(12) . . ? C5A N4A C3A 123.3(10) . . ? C5A N4A CuA 119.2(7) . . ? C3A N4A CuA 117.5(7) . . ? N4A C5A C15A 120.2(12) . . ? N4A C5A C6A 116.2(9) . . ? C15A C5A C6A 123.6(11) . . ? N7A C6A C5A 111.5(8) . . ? C6A N7A C8A 113.0(9) . . ? C6A N7A CuA 110.7(7) . . ? C8A N7A CuA 105.8(7) . . ? N7A C8A C9A 109.6(9) . . ? N10A C9A C8A 109.1(10) . . ? C9A N10A C11A 118.8(9) . . ? C9A N10A CuA 103.4(7) . . ? C11A N10A CuA 102.6(7) . . ? N10A C11A C12A 109.9(10) . . ? C11A C12A N1A 110.2(10) . . ? C14A C13A C3A 119.0(13) . . ? C15A C14A C13A 122.7(12) . . ? C14A C15A C5A 117.2(13) . . ? N4B CuB N7B 80.6(4) . . ? N4B CuB N10B 123.4(3) . . ? N7B CuB N10B 86.3(4) . . ? N4B CuB N1B 81.5(3) . . ? N7B CuB N1B 152.6(4) . . ? N10B CuB N1B 86.3(4) . . ? N4B CuB BrB 126.1(2) . . ? N7B CuB BrB 105.1(3) . . ? N10B CuB BrB 110.6(3) . . ? N1B CuB BrB 102.2(3) . . ? C2B N1B C12B 116.5(10) . . ? C2B N1B CuB 110.8(7) . . ? C12B N1B CuB 105.3(8) . . ? C3B C2B N1B 112.5(9) . . ? N4B C3B C13B 118.4(11) . . ? N4B C3B C2B 114.4(9) . . ? C13B C3B C2B 127.1(10) . . ? C5B N4B C3B 121.1(9) . . ? C5B N4B CuB 119.5(7) . . ? C3B N4B CuB 119.0(7) . . ? N4B C5B C15B 122.3(11) . . ? N4B C5B C6B 112.4(9) . . ? C15B C5B C6B 125.3(11) . . ? N7B C6B C5B 109.5(9) . . ? C8B N7B C6B 112.9(10) . . ? C8B N7B CuB 102.5(7) . . ? C6B N7B CuB 110.7(7) . . ? N7B C8B C9B 111.3(11) . . ? N10B C9B C8B 107.9(10) . . ? C11B N10B C9B 114.6(11) . . ? C11B N10B CuB 100.5(8) . . ? C9B N10B CuB 108.2(8) . . ? N10B C11B C12B 110.1(12) . . ? C11B C12B N1B 110.3(11) . . ? C14B C13B C3B 119.3(11) . . ? C13B C14B C15B 123.6(11) . . ? C5B C15B C14B 115.0(12) . . ? O122 Cl1 O141 118.8(13) . . ? O122 Cl1 O132 111.8(7) . . ? O141 Cl1 O132 34.4(9) . . ? O122 Cl1 O111 127.2(13) . . ? O141 Cl1 O111 110.1(8) . . ? O132 Cl1 O111 97.1(12) . . ? O122 Cl1 O131 72.0(11) . . ? O141 Cl1 O131 110.3(8) . . ? O132 Cl1 O131 143.4(10) . . ? O111 Cl1 O131 109.2(8) . . ? O122 Cl1 O112 110.6(7) . . ? O141 Cl1 O112 126.6(12) . . ? O132 Cl1 O112 109.0(7) . . ? O111 Cl1 O112 16.9(13) . . ? O131 Cl1 O112 102.8(12) . . ? O122 Cl1 O121 36.7(11) . . ? O141 Cl1 O121 110.1(8) . . ? O132 Cl1 O121 85.7(11) . . ? O111 Cl1 O121 108.9(8) . . ? O131 Cl1 O121 108.2(8) . . ? O112 Cl1 O121 97.2(13) . . ? O122 Cl1 O142 110.7(7) . . ? O141 Cl1 O142 73.5(10) . . ? O132 Cl1 O142 107.2(6) . . ? O111 Cl1 O142 100.7(12) . . ? O131 Cl1 O142 44.2(10) . . ? O112 Cl1 O142 107.4(7) . . ? O121 Cl1 O142 146.0(11) . . ? O122 O121 Cl1 69.4(8) . . ? O142 O131 Cl1 68.8(8) . . ? O142 O131 O122 115.5(11) . . ? Cl1 O131 O122 53.1(6) . . ? O132 O141 Cl1 73.7(9) . . ? O132 O141 O142 126.8(12) . . ? Cl1 O141 O142 54.2(6) . . ? O121 O122 Cl1 73.9(10) . . ? O121 O122 O131 128.1(11) . . ? Cl1 O122 O131 54.9(6) . . ? O141 O132 Cl1 71.9(8) . . ? O131 O142 Cl1 67.0(7) . . ? O131 O142 O141 111.1(12) . . ? Cl1 O142 O141 52.2(6) . . ? O21 Cl2 O22 108.9(9) . . ? O21 Cl2 O24 110.8(8) . . ? O22 Cl2 O24 108.0(7) . . ? O21 Cl2 O23 112.3(9) . . ? O22 Cl2 O23 107.1(7) . . ? O24 Cl2 O23 109.7(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4A C5A C6A N7A 9.6(14) . . . . ? C5A C6A N7A C8A 105.4(11) . . . . ? C6A N7A C8A C9A -83.7(12) . . . . ? N7A C8A C9A N10A -60.0(12) . . . . ? C8A C9A N10A C11A 159.9(10) . . . . ? C9A N10A C11A C12A -156.1(10) . . . . ? N10A C11A C12A N1A 59.5(13) . . . . ? C11A C12A N1A C2A 82.0(13) . . . . ? C12A N1A C2A C3A -106.4(12) . . . . ? N1A C2A C3A N4A -9.7(14) . . . . ? C2A C3A N4A C5A 178.3(10) . . . . ? C3A N4A C5A C6A -177.0(10) . . . . ? N4A C5A C6A N7A 9.6(14) . . . . ? N4B C5B C6B N7B 21.4(13) . . . . ? C5B C6B N7B C8B 85.1(12) . . . . ? C6B N7B C8B C9B -168.6(10) . . . . ? N7B C8B C9B N10B 52.6(14) . . . . ? C8B C9B N10B C11B 84.6(13) . . . . ? C9B N10B C11B C12B -170.4(11) . . . . ? N10B C11B C12B N1B 53.2(15) . . . . ? C11B C12B N1B C2B 102.6(13) . . . . ? C12B N1B C2B C3B -106.1(14) . . . . ? N1B C2B C3B N4B -12.6(16) . . . . ? C2B C3B N4B C5B 177.3(11) . . . . ? C3B N4B C5B C6B -176.1(10) . . . . ? N4B C5B C6B N7B 21.4(13) . . . . ? _diffrn_measured_fraction_theta_max 0.819 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.819 _refine_diff_density_max 1.193 _refine_diff_density_min -1.269 _refine_diff_density_rms 0.145 #======END data_2 _database_code_CSD 154181 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 Br Cu F6 N4 P' _chemical_formula_weight 508.74 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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 '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' 'Cu' 'Cu' 0.3201 1.2651 '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 8.559(3) _cell_length_b 9.592(3) _cell_length_c 11.803(3) _cell_angle_alpha 77.69(2) _cell_angle_beta 75.19(2) _cell_angle_gamma 88.56(2) _cell_volume 914.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 3.526 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6907 _diffrn_reflns_av_R_equivalents 0.1249 _diffrn_reflns_av_sigmaI/netI 0.1201 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.99 _reflns_number_total 4411 _reflns_number_gt 3092 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w==1/[\s^2^(Fo^2^)+(0.0560P)^2^+4.5609P] 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 4411 _refine_ls_number_parameters 223 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2043 _refine_ls_wR_factor_gt 0.1745 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.056 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.15542(9) 0.33602(8) 0.30318(7) 0.0324(2) Uani 1 d . . . Br Br -0.12977(9) 0.32496(10) 0.42787(9) 0.0609(3) Uani 1 d . . . N4 N 0.1787(7) 0.4458(6) 0.1409(5) 0.0396(12) Uani 1 d . . . N7 N 0.1475(7) 0.1703(6) 0.2213(5) 0.0417(13) Uani 1 d . . . H7 H 0.0478 0.1271 0.2525 0.050 Uiso 1 calc R . . N10 N 0.2717(7) 0.2069(7) 0.4094(6) 0.0481(15) Uani 1 d . . . H10 H 0.2230 0.2078 0.4874 0.058 Uiso 1 calc R . . N1 N 0.2297(7) 0.5249(6) 0.3259(5) 0.0395(12) Uani 1 d . . . H1 H 0.1755 0.5367 0.4002 0.047 Uiso 1 calc R . . C3 C 0.1966(9) 0.5864(8) 0.1231(7) 0.0466(16) Uani 1 d . . . C14 C 0.2191(10) 0.6701(10) 0.0092(8) 0.061(2) Uani 1 d . . . H14 H 0.2321 0.7688 -0.0048 0.073 Uiso 1 calc R . . C15 C 0.2217(11) 0.6021(11) -0.0833(7) 0.064(2) Uani 1 d . . . H15 H 0.2340 0.6558 -0.1608 0.077 Uiso 1 calc R . . C16 C 0.2064(10) 0.4569(11) -0.0620(7) 0.057(2) Uani 1 d . . . H16 H 0.2100 0.4116 -0.1248 0.068 Uiso 1 calc R . . C5 C 0.1859(8) 0.3785(9) 0.0526(6) 0.0434(15) Uani 1 d . . . C6 C 0.1698(12) 0.2174(9) 0.0917(7) 0.059(2) Uani 1 d . . . H6A H 0.0781 0.1840 0.0695 0.070 Uiso 1 calc R . . H6B H 0.2661 0.1756 0.0503 0.070 Uiso 1 calc R . . C8 C 0.2659(11) 0.0685(8) 0.2570(9) 0.060(2) Uani 1 d . . . H8A H 0.3739 0.1001 0.2090 0.072 Uiso 1 calc R . . H8B H 0.2432 -0.0247 0.2442 0.072 Uiso 1 calc R . . C9 C 0.2555(12) 0.0592(9) 0.3886(9) 0.065(2) Uani 1 d . . . H9A H 0.1525 0.0152 0.4373 0.078 Uiso 1 calc R . . H9B H 0.3411 0.0006 0.4115 0.078 Uiso 1 calc R . . C11 C 0.4405(9) 0.2572(10) 0.3811(9) 0.058(2) Uani 1 d . . . H11A H 0.4921 0.2576 0.2976 0.070 Uiso 1 calc R . . H11B H 0.4977 0.1922 0.4302 0.070 Uiso 1 calc R . . C12 C 0.4508(11) 0.4048(12) 0.4031(10) 0.069(3) Uani 1 d . . . H12A H 0.3837 0.4054 0.4828 0.083 Uiso 1 calc R . . H12B H 0.5615 0.4236 0.4034 0.083 Uiso 1 calc R . . C13 C 0.4036(9) 0.5222(9) 0.3193(8) 0.054(2) Uani 1 d . . . H13A H 0.4624 0.5169 0.2385 0.065 Uiso 1 calc R . . H13B H 0.4359 0.6114 0.3343 0.065 Uiso 1 calc R . . C2 C 0.1832(11) 0.6368(8) 0.2368(8) 0.056(2) Uani 1 d . . . H2A H 0.2529 0.7208 0.2204 0.067 Uiso 1 calc R . . H2B H 0.0728 0.6629 0.2681 0.067 Uiso 1 calc R . . P P -0.7695(3) 0.0933(2) 0.76299(18) 0.0523(5) Uani 1 d D . . F11 F -0.8782(14) 0.1278(19) 0.6716(10) 0.083(5) Uiso 0.40(2) d PD . . F21 F -0.6105(11) 0.1202(17) 0.6587(9) 0.075(5) Uiso 0.40(2) d PD . . F31 F -0.7695(16) 0.2522(11) 0.7736(19) 0.119(8) Uiso 0.40(2) d PD . . F41 F -0.6669(14) 0.0523(19) 0.8591(10) 0.086(5) Uiso 0.40(2) d PD . . F51 F -0.9300(11) 0.0619(17) 0.8709(9) 0.076(5) Uiso 0.40(2) d PD . . F61 F -0.7761(16) -0.0701(10) 0.7571(18) 0.109(7) Uiso 0.40(2) d PD . . F12 F -0.8920(10) 0.0755(13) 0.6834(9) 0.077(3) Uiso 0.60(2) d PD . . F22 F -0.6255(10) 0.0684(14) 0.6568(8) 0.088(4) Uiso 0.60(2) d PD . . F32 F -0.7606(11) 0.2607(8) 0.7035(11) 0.086(4) Uiso 0.60(2) d PD . . F42 F -0.6507(11) 0.1226(14) 0.8366(9) 0.096(4) Uiso 0.60(2) d PD . . F52 F -0.9191(10) 0.1225(14) 0.8648(8) 0.087(4) Uiso 0.60(2) d PD . . F62 F -0.7869(14) -0.0690(9) 0.8176(14) 0.141(6) Uiso 0.60(2) d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0347(4) 0.0306(4) 0.0343(4) -0.0112(3) -0.0104(3) 0.0085(3) Br 0.0430(4) 0.0714(6) 0.0718(6) -0.0355(5) -0.0051(4) 0.0084(4) N4 0.047(3) 0.038(3) 0.037(3) -0.014(2) -0.013(2) 0.010(2) N7 0.052(3) 0.033(3) 0.042(3) -0.013(3) -0.013(3) 0.007(2) N10 0.042(3) 0.060(4) 0.038(3) -0.005(3) -0.009(2) 0.018(3) N1 0.040(3) 0.040(3) 0.041(3) -0.019(3) -0.009(2) 0.010(2) C3 0.049(4) 0.039(4) 0.047(4) -0.002(3) -0.011(3) 0.009(3) C14 0.059(5) 0.050(4) 0.066(5) 0.004(4) -0.014(4) 0.004(4) C15 0.065(5) 0.079(6) 0.033(4) 0.007(4) -0.002(4) 0.015(5) C16 0.054(4) 0.079(6) 0.036(4) -0.017(4) -0.006(3) 0.006(4) C5 0.044(3) 0.054(4) 0.033(3) -0.012(3) -0.010(3) 0.005(3) C6 0.089(6) 0.049(4) 0.041(4) -0.020(4) -0.013(4) 0.001(4) C8 0.059(5) 0.034(4) 0.093(7) -0.028(4) -0.020(5) 0.012(3) C9 0.075(6) 0.040(4) 0.072(6) 0.004(4) -0.018(5) 0.009(4) C11 0.042(4) 0.067(5) 0.069(5) -0.018(5) -0.020(4) 0.013(4) C12 0.058(5) 0.089(7) 0.084(7) -0.047(6) -0.037(5) 0.019(5) C13 0.039(4) 0.055(5) 0.074(5) -0.031(4) -0.010(4) 0.003(3) C2 0.072(5) 0.035(4) 0.064(5) -0.016(4) -0.021(4) 0.014(4) P 0.0683(13) 0.0460(11) 0.0436(10) -0.0142(9) -0.0129(9) 0.0084(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N4 1.942(6) . ? Cu N10 2.003(6) . ? Cu N1 2.027(6) . ? Cu N7 2.039(5) . ? Cu Br 2.4991(14) . ? N4 C5 1.326(8) . ? N4 C3 1.327(9) . ? N7 C6 1.463(10) . ? N7 C8 1.467(10) . ? N7 H7 0.9100 . ? N10 C11 1.466(10) . ? N10 C9 1.505(11) . ? N10 H10 0.9100 . ? N1 C2 1.459(10) . ? N1 C13 1.470(9) . ? N1 H1 0.9100 . ? C3 C14 1.380(12) . ? C3 C2 1.498(11) . ? C14 C15 1.381(13) . ? C14 H14 0.9300 . ? C15 C16 1.365(14) . ? C15 H15 0.9300 . ? C16 C5 1.370(11) . ? C16 H16 0.9300 . ? C5 C6 1.515(12) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.516(14) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.502(13) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.455(14) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? P F62 1.548(8) . ? P F31 1.555(8) . ? P F42 1.562(7) . ? P F21 1.568(8) . ? P F22 1.572(7) . ? P F11 1.576(8) . ? P F52 1.581(7) . ? P F41 1.586(8) . ? P F61 1.587(8) . ? P F51 1.601(8) . ? P F32 1.604(7) . ? P F12 1.610(7) . ? F21 F22 0.523(16) . ? F31 F32 0.798(17) . ? F31 F42 1.750(15) . ? F31 F52 1.774(15) . ? F41 F42 0.674(16) . ? F51 F52 0.577(15) . ? F61 F62 0.699(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu N10 143.4(2) . . ? N4 Cu N1 81.7(2) . . ? N10 Cu N1 98.0(3) . . ? N4 Cu N7 81.7(2) . . ? N10 Cu N7 87.0(3) . . ? N1 Cu N7 158.1(2) . . ? N4 Cu Br 112.25(17) . . ? N10 Cu Br 103.92(18) . . ? N1 Cu Br 99.41(16) . . ? N7 Cu Br 100.06(18) . . ? C5 N4 C3 122.9(7) . . ? C5 N4 Cu 119.6(5) . . ? C3 N4 Cu 117.3(5) . . ? C6 N7 C8 114.9(7) . . ? C6 N7 Cu 112.5(5) . . ? C8 N7 Cu 106.3(4) . . ? C6 N7 H7 107.6 . . ? C8 N7 H7 107.6 . . ? Cu N7 H7 107.6 . . ? C11 N10 C9 112.9(7) . . ? C11 N10 Cu 109.6(5) . . ? C9 N10 Cu 106.5(5) . . ? C11 N10 H10 109.3 . . ? C9 N10 H10 109.3 . . ? Cu N10 H10 109.3 . . ? C2 N1 C13 114.9(7) . . ? C2 N1 Cu 107.0(4) . . ? C13 N1 Cu 109.7(4) . . ? C2 N1 H1 108.4 . . ? C13 N1 H1 108.4 . . ? Cu N1 H1 108.4 . . ? N4 C3 C14 120.2(8) . . ? N4 C3 C2 112.9(7) . . ? C14 C3 C2 126.9(7) . . ? C3 C14 C15 117.6(8) . . ? C3 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? C16 C15 C14 120.6(8) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C5 119.5(8) . . ? C15 C16 H16 120.3 . . ? C5 C16 H16 120.3 . . ? N4 C5 C16 119.1(8) . . ? N4 C5 C6 114.5(6) . . ? C16 C5 C6 126.4(7) . . ? N7 C6 C5 111.5(6) . . ? N7 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N7 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? N7 C8 C9 108.7(6) . . ? N7 C8 H8A 110.0 . . ? C9 C8 H8A 110.0 . . ? N7 C8 H8B 110.0 . . ? C9 C8 H8B 110.0 . . ? H8A C8 H8B 108.3 . . ? N10 C9 C8 109.3(7) . . ? N10 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? N10 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? N10 C11 C12 111.0(7) . . ? N10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? N10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 117.4(7) . . ? C13 C12 H12A 108.0 . . ? C11 C12 H12A 108.0 . . ? C13 C12 H12B 108.0 . . ? C11 C12 H12B 108.0 . . ? H12A C12 H12B 107.2 . . ? C12 C13 N1 114.7(8) . . ? C12 C13 H13A 108.6 . . ? N1 C13 H13A 108.6 . . ? C12 C13 H13B 108.6 . . ? N1 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? N1 C2 C3 110.4(6) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? F62 P F31 152.4(7) . . ? F62 P F42 94.4(5) . . ? F31 P F42 68.3(6) . . ? F62 P F21 107.7(6) . . ? F31 P F21 91.4(5) . . ? F42 P F21 81.6(7) . . ? F62 P F22 90.8(4) . . ? F31 P F22 110.3(6) . . ? F42 P F22 91.7(4) . . ? F21 P F22 19.2(6) . . ? F62 P F11 107.8(7) . . ? F31 P F11 90.9(5) . . ? F42 P F11 157.8(6) . . ? F21 P F11 91.8(5) . . ? F22 P F11 88.4(7) . . ? F62 P F52 90.9(5) . . ? F31 P F52 68.9(6) . . ? F42 P F52 90.7(4) . . ? F21 P F52 160.3(6) . . ? F22 P F52 177.0(5) . . ? F11 P F52 88.7(7) . . ? F62 P F41 69.7(6) . . ? F31 P F41 90.9(5) . . ? F42 P F41 24.7(6) . . ? F21 P F41 90.6(5) . . ? F22 P F41 93.2(7) . . ? F11 P F41 177.0(6) . . ? F52 P F41 89.7(6) . . ? F62 P F61 25.7(6) . . ? F31 P F61 177.5(6) . . ? F42 P F61 111.9(6) . . ? F21 P F61 91.1(5) . . ? F22 P F61 72.2(6) . . ? F11 P F61 89.2(5) . . ? F52 P F61 108.6(6) . . ? F41 P F61 88.9(5) . . ? F62 P F51 70.9(6) . . ? F31 P F51 89.8(5) . . ? F42 P F51 98.0(6) . . ? F21 P F51 178.5(6) . . ? F22 P F51 159.8(6) . . ? F11 P F51 89.2(5) . . ? F52 P F51 20.9(5) . . ? F41 P F51 88.4(5) . . ? F61 P F51 87.7(5) . . ? F62 P F32 176.7(5) . . ? F31 P F32 29.2(6) . . ? F42 P F32 88.9(4) . . ? F21 P F32 73.6(6) . . ? F22 P F32 90.0(4) . . ? F11 P F32 69.0(6) . . ? F52 P F32 88.2(4) . . ? F41 P F32 113.5(6) . . ? F61 P F32 152.5(6) . . ? F51 P F32 107.8(6) . . ? F62 P F12 89.8(4) . . ? F31 P F12 107.7(6) . . ? F42 P F12 175.8(5) . . ? F21 P F12 97.6(6) . . ? F22 P F12 88.6(4) . . ? F11 P F12 18.0(6) . . ? F52 P F12 88.9(4) . . ? F41 P F12 159.4(6) . . ? F61 P F12 72.2(6) . . ? F51 P F12 83.0(6) . . ? F32 P F12 87.0(4) . . ? F22 F21 P 80.8(11) . . ? F32 F31 P 78.8(8) . . ? F32 F31 F42 115.8(12) . . ? P F31 F42 56.0(4) . . ? F32 F31 F52 113.5(12) . . ? P F31 F52 56.2(4) . . ? F42 F31 F52 78.7(6) . . ? F42 F41 P 75.6(9) . . ? F52 F51 P 77.6(10) . . ? F62 F61 P 74.0(8) . . ? F21 F22 P 80.0(11) . . ? F31 F32 P 72.0(7) . . ? F41 F42 P 79.7(9) . . ? F41 F42 F31 129.3(13) . . ? P F42 F31 55.7(4) . . ? F51 F52 P 81.5(10) . . ? F51 F52 F31 136.3(12) . . ? P F52 F31 54.9(4) . . ? F61 F62 P 80.2(9) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.480 _refine_diff_density_min -1.247 _refine_diff_density_rms 0.142 #======END data_3 _database_code_CSD 154182 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 Cl2 N4 Ni O8' _chemical_formula_weight 477.93 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _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 8.162(2) _cell_length_b 8.874(2) _cell_length_c 13.989(2) _cell_angle_alpha 91.36(3) _cell_angle_beta 104.48(2) _cell_angle_gamma 113.52(2) _cell_volume 890.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 1.440 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CAD4 _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3742 _diffrn_reflns_av_R_equivalents 0.0108 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 26.03 _reflns_number_total 3500 _reflns_number_gt 3072 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w==1/[\s^2^(Fo^2^)+(0.1215P)^2^+1.9627P] 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 3500 _refine_ls_number_parameters 260 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.1943 _refine_ls_wR_factor_gt 0.1826 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.085 _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 Ni Ni 0.04362(7) 0.78572(7) 0.25016(4) 0.0339(2) Uani 1 d . . . N4 N -0.0692(5) 0.6711(4) 0.1262(3) 0.0307(8) Uani 1 d . . . N7 N -0.1729(6) 0.6418(5) 0.2835(3) 0.0377(9) Uani 1 d . . . H7 H -0.2522 0.6921 0.2761 0.045 Uiso 1 calc R . . C3 C -0.0026(6) 0.7324(6) 0.0511(3) 0.0337(9) Uani 1 d . . . N1 N 0.2412(5) 0.9110(5) 0.1967(3) 0.0365(9) Uani 1 d . . . H1 H 0.3251 0.8655 0.2102 0.044 Uiso 1 calc R . . C9A C -0.0079(11) 0.7876(10) 0.4512(5) 0.077(2) Uani 0.50 d P A 1 H9A1 H 0.0456 0.7813 0.5204 0.093 Uiso 0.50 calc PR A 1 H9A2 H -0.0792 0.8535 0.4476 0.093 Uiso 0.50 calc PR A 1 N10A N 0.1543(12) 0.8590(13) 0.3896(7) 0.0376(18) Uani 0.50 d P A 1 H10A H 0.2349 0.8114 0.4105 0.045 Uiso 0.50 calc PR A 1 C11A C 0.2659(17) 1.0413(14) 0.4125(9) 0.047(2) Uani 0.50 d P A 1 H11A H 0.1853 1.0985 0.3961 0.057 Uiso 0.50 calc PR A 1 H11B H 0.3326 1.0724 0.4829 0.057 Uiso 0.50 calc PR A 1 C12A C 0.3853(11) 1.0813(9) 0.3579(5) 0.0708(19) Uani 0.50 d P A 1 H12A H 0.4464 1.0068 0.3698 0.085 Uiso 0.50 calc PR A 1 H12B H 0.4799 1.1913 0.3878 0.085 Uiso 0.50 calc PR A 1 C9B C -0.0079(11) 0.7876(10) 0.4512(5) 0.077(2) Uani 0.50 d P A 2 H9B1 H -0.0760 0.8537 0.4272 0.093 Uiso 0.50 calc PR A 2 H9B2 H -0.0160 0.7726 0.5186 0.093 Uiso 0.50 calc PR A 2 N10B N 0.1669(13) 0.9552(17) 0.3680(7) 0.044(2) Uani 0.50 d P A 2 H10B H 0.1015 1.0183 0.3648 0.052 Uiso 0.50 calc PR A 2 C11B C 0.1686(17) 0.8846(16) 0.4607(9) 0.052(3) Uani 0.50 d P A 2 H11C H 0.2430 0.8211 0.4697 0.062 Uiso 0.50 calc PR A 2 H11D H 0.2186 0.9712 0.5172 0.062 Uiso 0.50 calc PR A 2 C12B C 0.3853(11) 1.0813(9) 0.3579(5) 0.0708(19) Uani 0.50 d P A 2 H12C H 0.4339 1.1910 0.3952 0.085 Uiso 0.50 calc PR A 2 H12D H 0.4734 1.0326 0.3793 0.085 Uiso 0.50 calc PR A 2 C16 C -0.3185(7) 0.4420(6) 0.0199(4) 0.0423(11) Uani 1 d . . . H16 H -0.4251 0.3436 0.0096 0.051 Uiso 1 calc R . . C14 C -0.0915(8) 0.6499(7) -0.0440(4) 0.0425(11) Uani 1 d . . . H14 H -0.0458 0.6909 -0.0970 0.051 Uiso 1 calc R . . C15 C -0.2505(8) 0.5046(7) -0.0591(4) 0.0455(12) Uani 1 d . . . H15 H -0.3130 0.4477 -0.1233 0.055 Uiso 1 calc R . . C5 C -0.2236(6) 0.5297(6) 0.1139(4) 0.0356(10) Uani 1 d . . . C2 C 0.1703(7) 0.8936(6) 0.0862(4) 0.0411(11) Uani 1 d . . . H2A H 0.2646 0.8930 0.0558 0.049 Uiso 1 calc R . . H2B H 0.1408 0.9863 0.0673 0.049 Uiso 1 calc R . . C8 C -0.1242(8) 0.6150(7) 0.3894(4) 0.0501(13) Uani 1 d . . . H8A H -0.0528 0.5487 0.3986 0.060 Uiso 1 calc R B 1 H8B H -0.2362 0.5576 0.4097 0.060 Uiso 1 calc R B 1 C13 C 0.3383(7) 1.0850(6) 0.2488(4) 0.0468(12) Uani 1 d . . . H13A H 0.4510 1.1439 0.2294 0.056 Uiso 1 calc R C 1 H13B H 0.2582 1.1424 0.2304 0.056 Uiso 1 calc R C 1 C6 C -0.2646(8) 0.4877(6) 0.2111(4) 0.0445(11) Uani 1 d . . . H6A H -0.3981 0.4400 0.2018 0.053 Uiso 1 calc R . . H6B H -0.2179 0.4071 0.2360 0.053 Uiso 1 calc R . . Cl1 Cl 0.73924(16) 1.00630(15) 0.18456(10) 0.0451(3) Uani 1 d . . . O11 O 0.6647(9) 1.1113(7) 0.1347(5) 0.0903(18) Uani 1 d . . . O12 O 0.5985(8) 0.8478(7) 0.1752(6) 0.106(2) Uani 1 d . . . O13 O 0.8838(10) 1.0056(9) 0.1484(6) 0.118(3) Uani 1 d . . . O14 O 0.8106(13) 1.0635(13) 0.2859(5) 0.152(4) Uani 1 d . . . Cl2 Cl 0.3268(2) 0.5452(2) 0.35012(10) 0.0525(4) Uani 1 d D . . O211 O 0.4580(18) 0.6971(14) 0.3280(11) 0.119(6) Uiso 0.483(12) d PD . . O221 O 0.391(2) 0.4237(16) 0.3403(11) 0.111(5) Uiso 0.483(12) d PD . . O231 O 0.1484(11) 0.5050(14) 0.2786(6) 0.059(3) Uiso 0.483(12) d PD . . O241 O 0.3197(16) 0.5874(15) 0.4450(6) 0.083(4) Uiso 0.483(12) d PD . . O232 O 0.2017(15) 0.5796(16) 0.2746(7) 0.075(3) Uiso 0.517(12) d PD . . O222 O 0.4333(11) 0.4849(11) 0.3065(6) 0.060(3) Uiso 0.517(12) d PD . . O242 O 0.243(2) 0.4225(17) 0.4072(11) 0.143(7) Uiso 0.517(12) d PD . . O212 O 0.448(2) 0.6947(16) 0.4152(12) 0.172(9) Uiso 0.517(12) d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0289(3) 0.0349(4) 0.0344(4) -0.0026(2) 0.0074(2) 0.0114(3) N4 0.0263(17) 0.0292(18) 0.0359(19) -0.0002(14) 0.0077(14) 0.0119(14) N7 0.038(2) 0.037(2) 0.040(2) 0.0044(16) 0.0152(17) 0.0159(17) C3 0.035(2) 0.032(2) 0.039(2) 0.0064(18) 0.0144(19) 0.0169(19) N1 0.0267(18) 0.0268(18) 0.052(2) -0.0008(16) 0.0093(16) 0.0089(15) C9A 0.087(5) 0.072(5) 0.058(4) -0.016(3) -0.006(4) 0.035(4) N10A 0.039(5) 0.036(5) 0.035(5) -0.004(4) 0.006(3) 0.016(4) C11A 0.047(6) 0.039(6) 0.044(6) -0.013(5) -0.002(5) 0.015(5) C12A 0.081(5) 0.063(4) 0.064(4) -0.015(3) -0.004(3) 0.041(4) C9B 0.087(5) 0.072(5) 0.058(4) -0.016(3) -0.006(4) 0.035(4) N10B 0.033(5) 0.053(6) 0.042(5) -0.010(5) 0.006(4) 0.019(5) C11B 0.052(7) 0.064(7) 0.038(6) -0.006(5) 0.005(5) 0.029(6) C12B 0.081(5) 0.063(4) 0.064(4) -0.015(3) -0.004(3) 0.041(4) C16 0.034(2) 0.036(2) 0.049(3) -0.005(2) 0.005(2) 0.0105(19) C14 0.048(3) 0.049(3) 0.039(2) 0.007(2) 0.016(2) 0.026(2) C15 0.048(3) 0.049(3) 0.036(2) -0.005(2) 0.003(2) 0.022(2) C5 0.031(2) 0.034(2) 0.043(2) 0.0013(19) 0.0119(19) 0.0138(18) C2 0.039(2) 0.038(2) 0.047(3) 0.007(2) 0.019(2) 0.012(2) C8 0.058(3) 0.056(3) 0.037(3) 0.010(2) 0.020(2) 0.021(3) C13 0.038(3) 0.026(2) 0.067(3) -0.002(2) 0.016(2) 0.0043(19) C6 0.045(3) 0.036(2) 0.045(3) 0.002(2) 0.015(2) 0.009(2) Cl1 0.0350(6) 0.0414(6) 0.0596(8) 0.0082(5) 0.0131(5) 0.0170(5) O11 0.103(4) 0.089(4) 0.122(5) 0.044(3) 0.049(4) 0.072(4) O12 0.061(3) 0.053(3) 0.177(7) 0.018(4) 0.015(4) 0.006(2) O13 0.107(5) 0.131(6) 0.196(8) 0.083(5) 0.103(5) 0.093(5) O14 0.142(7) 0.181(9) 0.072(4) -0.026(5) -0.010(4) 0.032(6) Cl2 0.0646(9) 0.0701(9) 0.0414(7) 0.0067(6) 0.0151(6) 0.0467(8) _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 Ni N4 1.805(4) . ? Ni N1 1.899(4) . ? Ni N7 1.900(4) . ? Ni N10A 1.906(9) . ? Ni N10B 1.959(10) . ? N4 C3 1.332(6) . ? N4 C5 1.346(6) . ? N7 C6 1.482(6) . ? N7 C8 1.486(6) . ? C3 C14 1.370(7) . ? C3 C2 1.513(7) . ? N1 C2 1.489(6) . ? N1 C13 1.491(6) . ? C9A C8 1.537(9) . ? C9A N10A 1.681(13) . ? N10A C11A 1.484(14) . ? C11A C12A 1.329(14) . ? C12A C13 1.483(9) . ? C9B C11B 1.320(15) . ? C9B C8 1.537(9) . ? N10B C11B 1.453(16) . ? N10B C12B 1.729(13) . ? C12B C13 1.483(9) . ? C16 C5 1.378(7) . ? C16 C15 1.388(8) . ? C14 C15 1.380(8) . ? C5 C6 1.500(7) . ? Cl1 O14 1.388(7) . ? Cl1 O12 1.393(5) . ? Cl1 O13 1.397(5) . ? Cl1 O11 1.412(5) . ? Cl2 O221 1.389(9) . ? Cl2 O241 1.392(8) . ? Cl2 O232 1.406(7) . ? Cl2 O242 1.417(9) . ? Cl2 O212 1.418(10) . ? Cl2 O222 1.426(7) . ? Cl2 O231 1.445(7) . ? Cl2 O211 1.446(9) . ? O211 O212 1.24(2) . ? O221 O222 0.764(15) . ? O221 O242 1.695(19) . ? O231 O232 0.644(12) . ? O241 O212 1.269(19) . ? O241 O242 1.371(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ni N1 85.01(17) . . ? N4 Ni N7 86.14(17) . . ? N1 Ni N7 171.15(16) . . ? N4 Ni N10A 167.1(4) . . ? N1 Ni N10A 102.1(3) . . ? N7 Ni N10A 86.7(3) . . ? N4 Ni N10B 166.3(4) . . ? N1 Ni N10B 87.6(3) . . ? N7 Ni N10B 101.0(3) . . ? N10A Ni N10B 26.5(4) . . ? C3 N4 C5 123.1(4) . . ? C3 N4 Ni 119.4(3) . . ? C5 N4 Ni 117.5(3) . . ? C6 N7 C8 114.3(4) . . ? C6 N7 Ni 108.1(3) . . ? C8 N7 Ni 110.4(3) . . ? N4 C3 C14 119.9(4) . . ? N4 C3 C2 111.7(4) . . ? C14 C3 C2 128.4(4) . . ? C2 N1 C13 115.2(4) . . ? C2 N1 Ni 109.9(3) . . ? C13 N1 Ni 110.0(3) . . ? C8 C9A N10A 98.2(5) . . ? C11A N10A C9A 113.3(8) . . ? C11A N10A Ni 112.5(9) . . ? C9A N10A Ni 110.3(5) . . ? C12A C11A N10A 107.1(9) . . ? C11A C12A C13 126.0(8) . . ? C11B C9B C8 127.3(8) . . ? C11B N10B C12B 114.3(8) . . ? C11B N10B Ni 112.7(10) . . ? C12B N10B Ni 107.0(5) . . ? C9B C11B N10B 104.6(9) . . ? C13 C12B N10B 99.5(5) . . ? C5 C16 C15 118.1(5) . . ? C3 C14 C15 118.4(5) . . ? C14 C15 C16 121.1(5) . . ? N4 C5 C16 119.4(4) . . ? N4 C5 C6 111.9(4) . . ? C16 C5 C6 128.7(4) . . ? N1 C2 C3 108.4(4) . . ? N7 C8 C9B 106.6(5) . . ? N7 C8 C9A 106.6(5) . . ? C9B C8 C9A 0.0(11) . . ? C12B C13 C12A 0.0(11) . . ? C12B C13 N1 108.8(5) . . ? C12A C13 N1 108.8(5) . . ? N7 C6 C5 108.5(4) . . ? O14 Cl1 O12 106.0(5) . . ? O14 Cl1 O13 108.3(6) . . ? O12 Cl1 O13 112.5(4) . . ? O14 Cl1 O11 110.0(5) . . ? O12 Cl1 O11 110.1(4) . . ? O13 Cl1 O11 109.9(4) . . ? O221 Cl2 O241 116.3(8) . . ? O221 Cl2 O232 125.8(7) . . ? O241 Cl2 O232 112.4(6) . . ? O221 Cl2 O242 74.3(9) . . ? O241 Cl2 O242 58.4(8) . . ? O232 Cl2 O242 115.3(8) . . ? O221 Cl2 O212 118.8(10) . . ? O241 Cl2 O212 53.7(8) . . ? O232 Cl2 O212 108.2(8) . . ? O242 Cl2 O212 108.6(9) . . ? O221 Cl2 O222 31.4(6) . . ? O241 Cl2 O222 138.1(6) . . ? O232 Cl2 O222 109.4(5) . . ? O242 Cl2 O222 105.7(7) . . ? O212 Cl2 O222 109.5(8) . . ? O221 Cl2 O231 111.5(7) . . ? O241 Cl2 O231 109.7(6) . . ? O232 Cl2 O231 26.1(5) . . ? O242 Cl2 O231 91.3(8) . . ? O212 Cl2 O231 129.1(8) . . ? O222 Cl2 O231 109.1(5) . . ? O221 Cl2 O211 107.3(8) . . ? O241 Cl2 O211 104.2(7) . . ? O232 Cl2 O211 81.4(8) . . ? O242 Cl2 O211 158.9(9) . . ? O212 Cl2 O211 51.5(9) . . ? O222 Cl2 O211 78.7(7) . . ? O231 Cl2 O211 107.0(7) . . ? O212 O211 Cl2 63.1(6) . . ? O222 O221 Cl2 77.0(9) . . ? O222 O221 O242 130.5(10) . . ? Cl2 O221 O242 53.6(5) . . ? O232 O231 Cl2 73.6(9) . . ? O212 O241 O242 121.4(10) . . ? O212 O241 Cl2 64.2(6) . . ? O242 O241 Cl2 61.7(6) . . ? O231 O232 Cl2 80.4(9) . . ? O221 O222 Cl2 71.6(8) . . ? O241 O242 Cl2 59.9(5) . . ? O241 O242 O221 100.3(8) . . ? Cl2 O242 O221 52.1(5) . . ? O211 O212 O241 126.1(10) . . ? O211 O212 Cl2 65.4(7) . . ? O241 O212 Cl2 62.1(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.491 _refine_diff_density_min -0.952 _refine_diff_density_rms 0.144