Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _publ_contact_author_email elena.rybak-akimova@tufts.edu _publ_contact_author_name 'Prof Elena Rybak-Akimova' _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0186 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name A.M.Herrera R.J.Staples S.V.Kryatov A.Y.Nazarenko ; E.V.Rybak-Akimova ; data_[Ni(L2c)](ClO4)2 _database_code_CSD 198022 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H29 Cl2 N5 Ni O8' _chemical_formula_weight 549.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/M loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 10.275(2) _cell_length_b 9.314(2) _cell_length_c 12.170(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.03(3) _cell_angle_gamma 90.00 _cell_volume 1164.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used none _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour magenta _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 1.114 _exptl_absorpt_correction_type PSI-SCAN _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.85 _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 ? _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 2329 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2202 _reflns_number_gt 1396 _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_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1241P)^2^+0.6076P] 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 2202 _refine_ls_number_parameters 205 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0992 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.2038 _refine_ls_wR_factor_gt 0.1737 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.78706(9) 0.7500 0.71725(7) 0.0680(4) Uani 1 d S . . Cl1 Cl 1.18617(19) 0.7500 0.49495(17) 0.0831(6) Uani 1 d S . . O1 O 1.0915(9) 0.7500 0.4150(9) 0.200(5) Uani 1 d S . . O2 O 1.1360(14) 0.8384(14) 0.5797(11) 0.149(5) Uani 0.50 d P . . O3 O 1.2943(9) 0.8262(14) 0.4519(9) 0.140(4) Uani 0.50 d P . . O4 O 1.2224(16) 0.6235(12) 0.5314(14) 0.160(5) Uani 0.50 d P . . Cl2 Cl 0.7001(4) 0.7500 1.0908(3) 0.1420(12) Uani 1 d S . . O5 O 0.6971(13) 0.7500 1.1967(7) 0.222(6) Uani 1 d S . . O6 O 0.6333(11) 0.8739(15) 1.0475(8) 0.264(5) Uani 1 d . . . O7 O 0.8096(14) 0.7500 1.0339(12) 0.232(6) Uani 1 d S . . C1 C 0.9862(15) 0.9025(18) 0.8404(9) 0.102(5) Uani 0.50 d PD . . C2 C 0.8762(15) 1.0133(17) 0.8279(13) 0.113(4) Uiso 0.50 d P . . H2A H 0.8900 1.0711 0.7638 0.080 Uiso 0.50 d PR . . H2B H 0.8773 1.0754 0.8909 0.080 Uiso 0.50 d PR . . N2 N 0.7539(12) 0.9401(13) 0.8153(9) 0.099(3) Uani 0.50 d P . . H2C H 0.7423 0.9043 0.8831 0.080 Uiso 0.50 d PR . . C3 C 0.6528(16) 1.0359(18) 0.7969(14) 0.095(5) Uiso 0.50 d P . . H3A H 0.6659 1.0981 0.7351 0.080 Uiso 0.50 d PR . . H3B H 0.6408 1.0937 0.8612 0.080 Uiso 0.50 d PR . . C4 C 0.5288(18) 0.932(2) 0.7826(14) 0.106(5) Uiso 0.50 d P . . H4A H 0.4537 0.9933 0.7871 0.080 Uiso 0.50 d PR . . H4B H 0.5257 0.8689 0.8446 0.080 Uiso 0.50 d PR . . C5 C 0.5093(14) 0.8394(14) 0.6896(12) 0.103(4) Uiso 0.50 d PD . . H5A H 0.5204 0.8967 0.6249 0.080 Uiso 0.50 d PR . . H5B H 0.4212 0.8050 0.6891 0.080 Uiso 0.50 d PR . . C13 C 1.1018(18) 0.919(2) 0.8916(13) 0.133(6) Uani 0.50 d PD . . H13A H 1.1296 1.0081 0.9239 0.080 Uiso 0.50 d PR . . N3 N 0.5987(8) 0.7154(11) 0.6825(7) 0.083(4) Uani 0.50 d PD . . C6 C 0.551(2) 0.6108(19) 0.7648(16) 0.119(7) Uiso 0.50 d PD . . H6A H 0.4610 0.5916 0.7462 0.080 Uiso 0.50 d PR . . H6B H 0.5532 0.6541 0.8364 0.080 Uiso 0.50 d PR . . C7 C 0.6142(15) 0.4753(17) 0.7722(13) 0.089(4) Uiso 0.50 d P . . H7A H 0.6060 0.4307 0.7012 0.080 Uiso 0.50 d PR . . H7B H 0.5715 0.4138 0.8236 0.080 Uiso 0.50 d PR . . C8 C 0.7711(15) 0.4735(18) 0.8020(11) 0.094(4) Uiso 0.50 d P . . H8A H 0.8028 0.3774 0.8129 0.080 Uiso 0.50 d PR . . H8B H 0.7829 0.5251 0.8697 0.080 Uiso 0.50 d PR . . N4 N 0.8490(8) 0.5420(9) 0.7155(7) 0.074(2) Uani 0.50 d P . . H4C H 0.8310 0.5014 0.6499 0.080 Uiso 0.50 d PR . . C9 C 0.9920(11) 0.5376(13) 0.7394(10) 0.089(3) Uiso 0.50 d P . . H9A H 1.0383 0.5296 0.6719 0.080 Uiso 0.50 d PR . . H9B H 1.0122 0.4546 0.7833 0.080 Uiso 0.50 d PR . . C10 C 1.0381(13) 0.6681(19) 0.7976(10) 0.089(4) Uani 0.50 d PD . . C11 C 1.1563(15) 0.682(3) 0.8528(13) 0.111(7) Uani 0.50 d PD . . H11A H 1.2123 0.5998 0.8580 0.080 Uiso 0.50 d PR . . C12 C 1.1891(16) 0.810(3) 0.9008(13) 0.121(11) Uani 0.50 d PD . . H12A H 1.2713 0.8181 0.9392 0.080 Uiso 0.50 d PR . . N5 N 0.8296(9) 0.8352(10) 0.5683(7) 0.080(2) Uani 0.50 d P . . H5C H 0.9165 0.8437 0.5631 0.080 Uiso 0.50 d PR . . H5D H 0.7953 0.9239 0.5641 0.080 Uiso 0.50 d PR . . C16 C 0.7772(9) 0.7500 0.4723(8) 0.090(2) Uiso 1 d S . . H16A H 0.8093 0.6534 0.4774 0.080 Uiso 0.50 d PR . . H16B H 0.8064 0.7908 0.4046 0.080 Uiso 0.50 d PR . . C15 C 0.6334(9) 0.7500 0.4753(8) 0.100(3) Uiso 1 d S . . H15A H 0.5995 0.7180 0.4054 0.080 Uiso 0.50 d PR . . H15B H 0.6028 0.8460 0.4873 0.080 Uiso 0.50 d PR . . C14 C 0.5793(12) 0.6483(13) 0.5704(9) 0.090(3) Uiso 0.50 d PD . . H14A H 0.4884 0.6297 0.5580 0.080 Uiso 0.50 d PR . . H14B H 0.6246 0.5583 0.5680 0.080 Uiso 0.50 d PR . . N1 N 0.9582(10) 0.7814(15) 0.7940(6) 0.071(5) Uani 0.50 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 0.0708(6) 0.0707(6) 0.0628(6) 0.000 0.0091(4) 0.000 Cl1 0.0703(11) 0.0982(16) 0.0813(12) 0.000 0.0127(9) 0.000 O1 0.100(6) 0.326(15) 0.173(8) 0.000 -0.025(6) 0.000 O2 0.154(10) 0.143(9) 0.153(10) -0.058(8) 0.060(8) -0.013(8) O3 0.088(6) 0.192(12) 0.142(8) 0.050(7) 0.041(6) 0.006(6) O4 0.180(13) 0.087(7) 0.217(15) 0.040(8) 0.052(11) 0.025(8) Cl2 0.162(3) 0.161(3) 0.104(2) 0.000 0.065(2) 0.000 O5 0.259(14) 0.325(17) 0.082(5) 0.000 0.032(7) 0.000 O6 0.268(11) 0.341(14) 0.185(7) 0.049(8) 0.038(7) 0.093(10) O7 0.253(13) 0.197(11) 0.253(13) 0.000 0.171(12) 0.000 C1 0.115(11) 0.124(11) 0.065(7) -0.009(7) 0.004(7) -0.068(10) N2 0.127(9) 0.089(8) 0.081(6) -0.009(6) 0.018(6) -0.001(7) C13 0.123(14) 0.178(19) 0.098(11) -0.002(12) -0.004(11) -0.071(13) N3 0.067(4) 0.098(14) 0.084(5) -0.012(5) 0.013(4) -0.004(5) N4 0.067(5) 0.077(5) 0.078(5) -0.007(4) 0.004(4) 0.006(4) C10 0.067(8) 0.138(12) 0.062(7) 0.014(7) 0.008(6) -0.024(8) C11 0.051(7) 0.19(2) 0.093(11) 0.023(12) -0.006(7) -0.004(9) C12 0.073(9) 0.21(3) 0.082(10) 0.001(11) -0.014(7) -0.057(14) N5 0.075(5) 0.089(6) 0.078(5) 0.006(5) 0.010(4) -0.006(5) N1 0.070(5) 0.080(17) 0.063(4) 0.006(5) 0.006(4) -0.001(5) 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 N1 1.998(10) . ? Ni N3 1.999(9) . ? Ni N5 2.034(8) . ? Ni N4 2.039(9) . ? Ni N2 2.166(11) . ? Cl1 O4 1.311(12) . ? Cl1 O1 1.364(9) . ? Cl1 O2 1.424(10) . ? Cl1 O3 1.426(9) . ? Cl2 O5 1.290(9) . ? Cl2 O7 1.332(11) . ? Cl2 O6 1.438(11) . ? C1 N1 1.29(2) . ? C1 C13 1.34(2) . ? C1 C2 1.54(2) . ? C2 N2 1.436(19) . ? N2 C3 1.38(2) . ? C3 C4 1.60(2) . ? C4 C5 1.44(2) . ? C5 N3 1.479(12) . ? C13 C12 1.36(3) . ? N3 C6 1.488(15) . ? N3 C14 1.511(12) . ? C6 C7 1.42(2) . ? C7 C8 1.65(2) . ? C8 N4 1.479(16) . ? N4 C9 1.494(14) . ? C9 C10 1.480(18) . ? C10 N1 1.34(2) . ? C10 C11 1.38(2) . ? C11 C12 1.37(2) . ? N5 C16 1.504(11) . ? C16 C15 1.479(12) . ? C15 C14 1.603(13) . ? 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 Ni N3 164.3(3) . . ? N1 Ni N5 99.1(4) . . ? N3 Ni N5 95.6(4) . . ? N1 Ni N4 82.6(4) . . ? N3 Ni N4 98.4(4) . . ? N5 Ni N4 106.8(4) . . ? N1 Ni N2 76.6(5) . . ? N3 Ni N2 95.0(4) . . ? N5 Ni N2 102.2(4) . . ? N4 Ni N2 146.6(4) . . ? O4 Cl1 O1 115.8(7) . . ? O4 Cl1 O2 112.3(10) . . ? O1 Cl1 O2 104.7(7) . . ? O4 Cl1 O3 110.7(9) . . ? O1 Cl1 O3 106.8(6) . . ? O2 Cl1 O3 105.9(8) . . ? O5 Cl2 O7 123.8(10) . . ? O5 Cl2 O6 110.3(5) . . ? O7 Cl2 O6 102.2(6) . . ? N1 C1 C13 119.5(19) . . ? N1 C1 C2 112.7(12) . . ? C13 C1 C2 127.8(16) . . ? N2 C2 C1 109.4(12) . . ? C3 N2 C2 111.4(13) . . ? C3 N2 Ni 124.2(11) . . ? C2 N2 Ni 107.5(9) . . ? N2 C3 C4 102.9(14) . . ? C5 C4 C3 123.2(15) . . ? C4 C5 N3 116.1(14) . . ? C1 C13 C12 122(2) . . ? C5 N3 C6 104.9(10) . . ? C5 N3 C14 107.7(9) . . ? C6 N3 C14 107.2(11) . . ? C5 N3 Ni 117.5(8) . . ? C6 N3 Ni 107.2(10) . . ? C14 N3 Ni 111.7(6) . . ? C6 C7 C8 118.0(14) . . ? N4 C8 C7 112.2(11) . . ? C8 N4 C9 113.1(9) . . ? C8 N4 Ni 103.3(8) . . ? C9 N4 Ni 109.3(7) . . ? C10 C9 N4 112.0(10) . . ? N1 C10 C11 118.3(17) . . ? N1 C10 C9 116.2(10) . . ? C11 C10 C9 125.4(17) . . ? C12 C11 C10 119.8(17) . . ? C13 C12 C11 117.3(14) . . ? C16 N5 Ni 114.0(6) . . ? C15 C16 N5 109.0(7) . . ? C16 C15 C14 112.2(7) . . ? N3 C14 C15 111.5(9) . . ? C1 N1 C10 122.9(13) . . ? C1 N1 Ni 121.3(11) . . ? C10 N1 Ni 115.7(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.446 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.072 #===END data_[Ni(L2a)](ClO4)2 _database_code_CSD 198023 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H33 Cl2 N5 Ni O8' _chemical_formula_weight 577.10 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.5147(17) _cell_length_b 16.5059(13) _cell_length_c 16.3212(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.227(2) _cell_angle_gamma 90.00 _cell_volume 4948.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2416 _exptl_absorpt_coefficient_mu 1.053 _exptl_absorpt_correction_type 'Empirical, SADABS' _exptl_absorpt_correction_T_min 0.345126 _exptl_absorpt_correction_T_max 0.942202 _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-2 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 33552 _diffrn_reflns_av_R_equivalents 0.0856 _diffrn_reflns_av_sigmaI/netI 0.0948 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.96 _reflns_number_total 10739 _reflns_number_gt 5244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.1309P)^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 10739 _refine_ls_number_parameters 617 _refine_ls_number_restraints 168 _refine_ls_R_factor_all 0.1550 _refine_ls_R_factor_gt 0.0767 _refine_ls_wR_factor_ref 0.2505 _refine_ls_wR_factor_gt 0.2024 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.004 _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 0.07931(4) 0.34363(4) 0.81456(5) 0.0405(2) Uani 1 1 d . . . N1 N -0.0202(3) 0.3054(3) 0.7685(3) 0.0423(11) Uani 1 1 d . . . N2 N 0.0740(3) 0.3866(3) 0.6919(3) 0.0441(11) Uani 1 1 d . . . H2B H 0.0969 0.4360 0.6909 0.053 Uiso 1 1 calc R . . N3 N 0.1908(3) 0.3313(3) 0.8297(3) 0.0484(12) Uani 1 1 d . . . N4 N 0.0606(3) 0.2560(3) 0.9056(3) 0.0471(12) Uani 1 1 d . . . H4C H 0.0761 0.2756 0.9577 0.057 Uiso 1 1 calc R . . N5 N 0.0734(3) 0.4432(3) 0.8853(3) 0.0520(13) Uani 1 1 d . . . H5A H 0.0288 0.4663 0.8719 0.062 Uiso 1 1 calc R . . H5B H 0.0766 0.4273 0.9391 0.062 Uiso 1 1 calc R . . C1 C -0.0453(3) 0.3260(3) 0.6909(4) 0.0444(14) Uani 1 1 d U . . C2 C -0.0039(3) 0.3939(3) 0.6565(4) 0.0476(15) Uani 1 1 d U . . H2 H -0.0081 0.3887 0.5956 0.057 Uiso 1 1 calc R . . C3 C 0.1120(3) 0.3252(4) 0.6460(4) 0.0519(15) Uani 1 1 d U . . H3A H 0.1036 0.3377 0.5869 0.062 Uiso 1 1 calc R . . H3B H 0.0909 0.2717 0.6539 0.062 Uiso 1 1 calc R . . C4 C 0.1929(4) 0.3216(4) 0.6730(4) 0.0611(18) Uani 1 1 d U . . H4A H 0.2125 0.3767 0.6724 0.073 Uiso 1 1 calc R . . H4B H 0.2155 0.2897 0.6325 0.073 Uiso 1 1 calc R . . C5 C 0.2155(4) 0.2849(4) 0.7595(4) 0.0564(16) Uani 1 1 d U . . H5C H 0.1959 0.2298 0.7602 0.068 Uiso 1 1 calc R . . H5D H 0.2687 0.2808 0.7686 0.068 Uiso 1 1 calc R . . C6 C 0.2153(4) 0.2867(4) 0.9083(4) 0.0558(16) Uani 1 1 d U . . H6A H 0.2001 0.3177 0.9544 0.067 Uiso 1 1 calc R . . H6B H 0.2686 0.2850 0.9159 0.067 Uiso 1 1 calc R . . C7 C 0.1869(3) 0.2006(4) 0.9127(4) 0.0541(16) Uani 1 1 d U . . H7A H 0.1986 0.1816 0.9697 0.065 Uiso 1 1 calc R . . H7B H 0.2137 0.1663 0.8779 0.065 Uiso 1 1 calc R . . C8 C 0.1056(4) 0.1871(3) 0.8868(4) 0.0546(16) Uani 1 1 d U . . H8A H 0.0975 0.1767 0.8272 0.065 Uiso 1 1 calc R . . H8B H 0.0902 0.1389 0.9150 0.065 Uiso 1 1 calc R . . C9 C -0.0184(3) 0.2361(3) 0.8977(4) 0.0506(15) Uani 1 1 d U . . H9 H -0.0250 0.1794 0.9150 0.061 Uiso 1 1 calc R . . C10 C -0.0507(3) 0.2470(3) 0.8084(4) 0.0438(14) Uani 1 1 d U . . C11 C -0.1092(3) 0.2031(4) 0.7698(4) 0.0523(16) Uani 1 1 d U . . H11 H -0.1301 0.1605 0.7970 0.063 Uiso 1 1 calc R . . C12 C -0.1355(3) 0.2241(4) 0.6903(4) 0.0576(17) Uani 1 1 d U . . H12 H -0.1753 0.1956 0.6628 0.069 Uiso 1 1 calc R . . C13 C -0.1047(3) 0.2865(4) 0.6499(4) 0.0523(16) Uani 1 1 d U . . H13 H -0.1238 0.3015 0.5959 0.063 Uiso 1 1 calc R . . C14 C 0.2280(4) 0.4122(4) 0.8349(5) 0.0641(19) Uani 1 1 d U . . H14A H 0.2196 0.4378 0.7804 0.077 Uiso 1 1 calc R . . H14B H 0.2805 0.4032 0.8478 0.077 Uiso 1 1 calc R . . C15 C 0.2045(4) 0.4707(4) 0.8977(5) 0.069(2) Uani 1 1 d U . . H15A H 0.2074 0.4428 0.9510 0.083 Uiso 1 1 calc R . . H15B H 0.2395 0.5155 0.9041 0.083 Uiso 1 1 calc R . . C16 C 0.1296(4) 0.5055(4) 0.8780(4) 0.0618(18) Uani 1 1 d U . . H16A H 0.1234 0.5502 0.9160 0.074 Uiso 1 1 calc R . . H16B H 0.1237 0.5272 0.8217 0.074 Uiso 1 1 calc R . . C17 C -0.0337(4) 0.4754(4) 0.6787(4) 0.0578(17) Uani 1 1 d U . . H17A H -0.0327 0.4790 0.7382 0.087 Uiso 1 1 calc R . . H17B H -0.0834 0.4810 0.6525 0.087 Uiso 1 1 calc R . . H17C H -0.0039 0.5182 0.6598 0.087 Uiso 1 1 calc R . . C18 C -0.0564(4) 0.2934(4) 0.9518(4) 0.0644(19) Uani 1 1 d U . . H18A H -0.0353 0.2873 1.0089 0.097 Uiso 1 1 calc R . . H18B H -0.1079 0.2804 0.9466 0.097 Uiso 1 1 calc R . . H18C H -0.0503 0.3488 0.9342 0.097 Uiso 1 1 calc R . . Ni1A Ni 0.41706(5) 0.60009(5) 0.24915(6) 0.0597(3) Uani 1 1 d . . . N1A N 0.5189(4) 0.5695(4) 0.2860(4) 0.0744(18) Uani 1 1 d . . . N2A N 0.4266(5) 0.6392(5) 0.3709(5) 0.099(3) Uani 1 1 d . . . H2AA H 0.4021 0.6875 0.3731 0.119 Uiso 1 1 calc R . . N3A N 0.3061(3) 0.5897(4) 0.2358(4) 0.0696(17) Uani 1 1 d . . . N4A N 0.4347(4) 0.5130(7) 0.1616(8) 0.182(6) Uani 1 1 d . . . H4AA H 0.4201 0.5438 0.1155 0.218 Uiso 1 1 calc R . . N5A N 0.4207(4) 0.7003(5) 0.1809(6) 0.116(3) Uani 1 1 d . . . H5A1 H 0.4638 0.7252 0.1979 0.140 Uiso 1 1 calc R . . H5A2 H 0.4224 0.6840 0.1279 0.140 Uiso 1 1 calc R . . C1A C 0.5489(6) 0.5905(7) 0.3629(7) 0.110(4) Uani 1 1 d U . . C2A C 0.5023(8) 0.6513(8) 0.4046(6) 0.137(5) Uani 1 1 d U . . H2A H 0.5076 0.6397 0.4646 0.164 Uiso 1 1 calc R . . C3A C 0.3902(6) 0.5778(6) 0.4150(6) 0.107(3) Uani 1 1 d U . . H3A1 H 0.4013 0.5876 0.4745 0.129 Uiso 1 1 calc R . . H3A2 H 0.4100 0.5245 0.4034 0.129 Uiso 1 1 calc R . . C4A C 0.3086(6) 0.5759(6) 0.3925(7) 0.107(3) Uani 1 1 d U . . H4A1 H 0.2898 0.6311 0.3958 0.128 Uiso 1 1 calc R . . H4A2 H 0.2875 0.5430 0.4334 0.128 Uiso 1 1 calc R . . C5A C 0.2819(6) 0.5403(7) 0.3019(8) 0.129(4) Uani 1 1 d U . . H5A3 H 0.3007 0.4851 0.2981 0.155 Uiso 1 1 calc R . . H5A4 H 0.2286 0.5374 0.2941 0.155 Uiso 1 1 calc R . . C6A C 0.2777(5) 0.5430(6) 0.1561(7) 0.107(3) Uani 1 1 d U . . H6A1 H 0.2252 0.5352 0.1554 0.129 Uiso 1 1 calc R . . H6A2 H 0.2846 0.5777 0.1089 0.129 Uiso 1 1 calc R . . C7A C 0.3106(4) 0.4632(5) 0.1426(6) 0.080(2) Uani 1 1 d U . . H7AA H 0.2891 0.4435 0.0883 0.095 Uiso 1 1 calc R . . H7AB H 0.2957 0.4257 0.1839 0.095 Uiso 1 1 calc R . . C8A C 0.3912(5) 0.4579(5) 0.1460(9) 0.129(5) Uani 1 1 d U . . H8AA H 0.4064 0.4151 0.1862 0.155 Uiso 1 1 calc R . . H8AB H 0.4002 0.4368 0.0921 0.155 Uiso 1 1 calc R . . C9A C 0.5123(5) 0.5065(7) 0.1500(8) 0.126(5) Uani 1 1 d U . . H9A H 0.5221 0.4508 0.1316 0.151 Uiso 1 1 calc R . . C10A C 0.5522(5) 0.5191(5) 0.2378(7) 0.092(3) Uani 1 1 d U . . C11A C 0.6191(6) 0.4847(7) 0.2665(10) 0.130(5) Uani 1 1 d U . . H11A H 0.6423 0.4484 0.2340 0.156 Uiso 1 1 calc R . . C12A C 0.6487(7) 0.5055(10) 0.3422(12) 0.172(8) Uani 1 1 d U . . H12A H 0.6940 0.4828 0.3626 0.207 Uiso 1 1 calc R . . C13A C 0.6159(8) 0.5600(11) 0.3939(9) 0.160(7) Uani 1 1 d U . . H13A H 0.6388 0.5745 0.4465 0.192 Uiso 1 1 calc R . . C14A C 0.2680(5) 0.6656(6) 0.2260(8) 0.125(4) Uani 1 1 d U . . H14C H 0.2688 0.6889 0.2813 0.150 Uiso 1 1 calc R . . H14D H 0.2170 0.6530 0.2064 0.150 Uiso 1 1 calc R . . C15A C 0.2905(5) 0.7305(5) 0.1721(6) 0.091(3) Uani 1 1 d U . . H15C H 0.2606 0.7781 0.1803 0.110 Uiso 1 1 calc R . . H15D H 0.2769 0.7127 0.1149 0.110 Uiso 1 1 calc R . . C16A C 0.3670(5) 0.7585(5) 0.1787(7) 0.103(3) Uani 1 1 d U . . H16C H 0.3716 0.7943 0.1318 0.123 Uiso 1 1 calc R . . H16D H 0.3767 0.7913 0.2289 0.123 Uiso 1 1 calc R . . C17A C 0.5297(10) 0.7359(8) 0.3922(8) 0.215(9) Uani 1 1 d U . . H17D H 0.5342 0.7442 0.3342 0.323 Uiso 1 1 calc R . . H17E H 0.5769 0.7430 0.4246 0.323 Uiso 1 1 calc R . . H17F H 0.4957 0.7750 0.4097 0.323 Uiso 1 1 calc R . . C18A C 0.5402(6) 0.5652(9) 0.0926(7) 0.144(5) Uani 1 1 d U . . H18D H 0.5045 0.5720 0.0443 0.217 Uiso 1 1 calc R . . H18E H 0.5853 0.5449 0.0758 0.217 Uiso 1 1 calc R . . H18F H 0.5491 0.6169 0.1202 0.217 Uiso 1 1 calc R . . Cl1 Cl 0.15224(9) 0.54000(9) 0.55713(10) 0.0519(4) Uani 1 1 d . . . O1 O 0.0769(3) 0.5321(6) 0.5339(4) 0.148(3) Uani 1 1 d . . . O2 O 0.1896(3) 0.4799(3) 0.5175(3) 0.0918(18) Uani 1 1 d . . . O3 O 0.1663(3) 0.5308(3) 0.6457(3) 0.0630(12) Uani 1 1 d . . . O4 O 0.1727(5) 0.6171(3) 0.5346(4) 0.119(3) Uani 1 1 d . . . Cl2 Cl 0.33037(16) 0.66378(13) 0.94068(16) 0.0998(9) Uani 1 1 d . . . O5 O 0.3190(6) 0.6642(7) 0.8588(5) 0.197(5) Uani 1 1 d . . . O6 O 0.2559(5) 0.6647(6) 0.9684(6) 0.168(4) Uani 1 1 d . . . O7 O 0.3629(4) 0.5936(4) 0.9741(5) 0.127(3) Uani 1 1 d . . . O8 O 0.3657(7) 0.7308(6) 0.9795(8) 0.246(7) Uani 1 1 d . . . Cl3 Cl 0.09228(9) 0.09231(9) 0.62706(10) 0.0508(4) Uani 1 1 d . . . O9 O 0.1159(3) 0.1399(3) 0.5604(3) 0.0703(14) Uani 1 1 d . . . O10 O 0.0247(3) 0.1229(3) 0.6471(4) 0.0792(15) Uani 1 1 d . . . O11 O 0.0848(3) 0.0095(3) 0.6020(3) 0.0786(15) Uani 1 1 d . . . O12 O 0.1452(3) 0.0983(3) 0.6976(3) 0.0740(14) Uani 1 1 d . . . Cl4 Cl 0.41406(12) 0.32180(14) 0.35824(14) 0.0785(6) Uani 1 1 d . . . O13 O 0.3559(5) 0.3569(5) 0.3750(11) 0.249(8) Uani 1 1 d . . . O14 O 0.4216(8) 0.2618(7) 0.4116(8) 0.262(7) Uani 1 1 d . . . O15 O 0.4041(7) 0.2876(10) 0.2853(6) 0.265(8) Uani 1 1 d . . . O16 O 0.4747(4) 0.3688(6) 0.3646(6) 0.171(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0396(4) 0.0443(4) 0.0364(4) 0.0026(3) -0.0004(3) -0.0035(3) N1 0.040(3) 0.049(2) 0.037(3) -0.002(2) 0.000(2) 0.000(2) N2 0.040(3) 0.050(2) 0.042(3) 0.001(2) 0.001(2) -0.005(2) N3 0.047(3) 0.050(3) 0.047(3) 0.001(2) 0.001(3) -0.004(2) N4 0.042(3) 0.053(3) 0.044(3) 0.005(2) -0.004(2) -0.004(2) N5 0.055(3) 0.058(3) 0.041(3) -0.002(2) -0.003(3) 0.002(2) C1 0.041(3) 0.056(3) 0.036(3) -0.003(3) 0.004(3) 0.008(3) C2 0.048(4) 0.057(3) 0.035(3) 0.005(3) -0.003(3) 0.007(3) C3 0.054(4) 0.061(3) 0.042(4) 0.002(3) 0.009(3) 0.007(3) C4 0.056(4) 0.078(4) 0.053(4) 0.010(3) 0.021(4) 0.011(3) C5 0.051(4) 0.066(4) 0.055(4) 0.007(3) 0.017(3) 0.004(3) C6 0.046(4) 0.065(4) 0.053(4) 0.006(3) -0.007(3) 0.008(3) C7 0.050(4) 0.062(4) 0.049(4) 0.014(3) 0.000(3) 0.011(3) C8 0.066(4) 0.045(3) 0.051(4) 0.000(3) 0.002(3) 0.002(3) C9 0.047(4) 0.050(3) 0.053(4) 0.008(3) -0.004(3) -0.007(3) C10 0.041(3) 0.048(3) 0.043(3) -0.003(3) 0.008(3) -0.001(3) C11 0.040(3) 0.054(3) 0.062(4) -0.004(3) 0.003(3) -0.003(3) C12 0.039(4) 0.061(4) 0.069(5) -0.017(3) -0.006(3) -0.002(3) C13 0.045(4) 0.068(4) 0.043(4) -0.012(3) -0.002(3) 0.009(3) C14 0.042(4) 0.075(4) 0.072(5) 0.008(4) -0.003(4) -0.016(3) C15 0.063(5) 0.063(4) 0.078(5) -0.008(4) -0.008(4) -0.019(3) C16 0.079(5) 0.049(3) 0.056(4) -0.004(3) 0.001(4) -0.008(3) C17 0.056(4) 0.056(3) 0.061(4) 0.008(3) 0.005(4) 0.015(3) C18 0.060(4) 0.087(5) 0.048(4) -0.003(4) 0.017(4) -0.007(4) Ni1A 0.0560(6) 0.0676(5) 0.0559(6) -0.0059(4) 0.0082(5) 0.0074(4) N1A 0.065(4) 0.070(4) 0.082(5) 0.011(3) -0.016(4) -0.006(3) N2A 0.130(7) 0.096(5) 0.078(5) -0.024(4) 0.041(5) -0.036(5) N3A 0.056(4) 0.075(4) 0.081(5) 0.010(3) 0.022(4) 0.012(3) N4A 0.042(4) 0.237(11) 0.266(13) -0.200(11) 0.018(6) -0.016(6) N5A 0.077(5) 0.134(7) 0.141(8) 0.065(6) 0.029(5) 0.014(5) C1A 0.084(7) 0.160(9) 0.079(7) 0.044(7) -0.019(6) -0.061(7) C2A 0.169(12) 0.184(11) 0.058(6) -0.019(7) 0.016(7) -0.111(10) C3A 0.144(10) 0.112(7) 0.066(6) 0.013(5) 0.015(6) -0.048(7) C4A 0.132(9) 0.103(6) 0.098(8) -0.009(6) 0.066(7) -0.009(6) C5A 0.083(7) 0.145(9) 0.162(11) 0.059(9) 0.027(8) -0.009(7) C6A 0.066(6) 0.127(8) 0.126(9) 0.014(7) -0.002(6) -0.008(6) C7A 0.056(5) 0.077(5) 0.102(7) 0.000(5) -0.008(5) -0.006(4) C8A 0.075(7) 0.059(4) 0.259(15) -0.020(7) 0.045(8) -0.004(4) C9A 0.056(6) 0.151(9) 0.173(12) -0.100(9) 0.026(7) -0.003(6) C10A 0.048(5) 0.086(5) 0.142(9) 0.004(6) 0.013(5) -0.011(4) C11A 0.060(6) 0.105(7) 0.225(15) 0.059(9) 0.019(8) -0.001(5) C12A 0.064(8) 0.205(15) 0.232(19) 0.142(14) -0.044(10) -0.029(9) C13A 0.107(11) 0.239(16) 0.117(11) 0.090(11) -0.058(8) -0.079(10) C14A 0.069(6) 0.099(6) 0.210(13) 0.041(7) 0.030(7) 0.016(5) C15A 0.075(6) 0.074(5) 0.129(8) 0.018(5) 0.030(6) 0.027(4) C16A 0.087(7) 0.081(5) 0.146(9) 0.032(6) 0.034(7) 0.009(5) C17A 0.35(2) 0.189(13) 0.121(11) -0.077(10) 0.074(13) -0.181(15) C18A 0.072(7) 0.246(16) 0.112(9) -0.089(10) 0.001(7) 0.008(9) Cl1 0.0471(9) 0.0647(9) 0.0434(9) 0.0070(7) 0.0040(7) 0.0061(7) O1 0.052(4) 0.304(11) 0.081(5) 0.017(6) -0.021(3) 0.011(5) O2 0.118(5) 0.083(3) 0.078(4) -0.014(3) 0.025(4) 0.027(3) O3 0.078(3) 0.068(3) 0.040(3) 0.004(2) -0.001(2) 0.004(2) O4 0.204(8) 0.064(3) 0.097(5) 0.021(3) 0.054(5) -0.011(4) Cl2 0.115(2) 0.0827(13) 0.0880(17) 0.0264(12) -0.0425(15) -0.0213(13) O5 0.193(10) 0.326(14) 0.070(5) 0.060(7) 0.007(6) 0.084(9) O6 0.108(7) 0.245(10) 0.139(8) -0.042(7) -0.035(6) 0.051(7) O7 0.127(6) 0.137(6) 0.111(6) 0.040(5) -0.014(5) 0.045(5) O8 0.287(15) 0.188(9) 0.245(13) 0.049(9) -0.043(11) -0.160(10) Cl3 0.0525(9) 0.0560(8) 0.0429(9) 0.0022(7) 0.0023(7) 0.0021(7) O9 0.082(4) 0.078(3) 0.052(3) 0.012(2) 0.015(3) 0.000(3) O10 0.062(3) 0.089(3) 0.090(4) 0.011(3) 0.025(3) 0.016(3) O11 0.090(4) 0.058(3) 0.088(4) -0.014(3) 0.010(3) -0.007(3) O12 0.071(3) 0.093(3) 0.052(3) 0.004(3) -0.015(3) 0.002(3) Cl4 0.0685(13) 0.0978(14) 0.0687(13) 0.0039(11) 0.0061(11) 0.0083(11) O13 0.110(7) 0.118(6) 0.54(3) -0.029(10) 0.142(11) 0.003(5) O14 0.330(19) 0.166(9) 0.261(14) 0.093(10) -0.072(13) 0.002(10) O15 0.250(14) 0.45(2) 0.108(7) -0.124(11) 0.058(8) -0.158(14) O16 0.093(6) 0.233(9) 0.189(10) -0.016(8) 0.023(6) -0.073(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 2.002(5) . ? Ni1 N5 2.019(5) . ? Ni1 N3 2.057(5) . ? Ni1 N2 2.115(5) . ? Ni1 N4 2.133(5) . ? N1 C10 1.329(7) . ? N1 C1 1.337(7) . ? N2 C3 1.489(7) . ? N2 C2 1.490(7) . ? N2 H2B 0.9200 . ? N3 C5 1.498(8) . ? N3 C6 1.499(8) . ? N3 C14 1.499(7) . ? N4 C8 1.465(7) . ? N4 C9 1.490(8) . ? N4 H4C 0.9200 . ? N5 C16 1.479(8) . ? N5 H5A 0.9100 . ? N5 H5B 0.9100 . ? C1 C13 1.378(8) . ? C1 C2 1.504(8) . ? C2 C17 1.515(8) . ? C2 H2 0.9900 . ? C3 C4 1.508(9) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 C5 1.544(9) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 H5C 0.9800 . ? C5 H5D 0.9800 . ? C6 C7 1.520(9) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.527(9) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 C10 1.515(8) . ? C9 C18 1.524(9) . ? C9 H9 0.9900 . ? C10 C11 1.388(8) . ? C11 C12 1.371(9) . ? C11 H11 0.9400 . ? C12 C13 1.385(9) . ? C12 H12 0.9400 . ? C13 H13 0.9400 . ? C14 C15 1.510(10) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 C16 1.498(10) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? Ni1A N1A 1.971(7) . ? Ni1A N5A 2.000(7) . ? Ni1A N3A 2.047(6) . ? Ni1A N2A 2.076(7) . ? Ni1A N4A 2.081(7) . ? N1A C10A 1.346(11) . ? N1A C1A 1.353(12) . ? N2A C2A 1.453(14) . ? N2A C3A 1.457(10) . ? N2A H2AA 0.9200 . ? N3A C14A 1.436(10) . ? N3A C5A 1.466(11) . ? N3A C6A 1.545(11) . ? N4A C8A 1.221(11) . ? N4A C9A 1.478(11) . ? N4A H4AA 0.9200 . ? N5A C16A 1.380(10) . ? N5A H5A1 0.9100 . ? N5A H5A2 0.9100 . ? C1A C13A 1.374(17) . ? C1A C2A 1.537(17) . ? C2A C17A 1.509(14) . ? C2A H2A 0.9900 . ? C3A C4A 1.509(14) . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C4A C5A 1.609(14) . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C5A H5A3 0.9800 . ? C5A H5A4 0.9800 . ? C6A C7A 1.479(12) . ? C6A H6A1 0.9800 . ? C6A H6A2 0.9800 . ? C7A C8A 1.489(11) . ? C7A H7AA 0.9800 . ? C7A H7AB 0.9800 . ? C8A H8AA 0.9800 . ? C8A H8AB 0.9800 . ? C9A C18A 1.484(17) . ? C9A C10A 1.541(15) . ? C9A H9A 0.9900 . ? C10A C11A 1.389(13) . ? C11A C12A 1.33(2) . ? C11A H11A 0.9400 . ? C12A C13A 1.42(2) . ? C12A H12A 0.9400 . ? C13A H13A 0.9400 . ? C14A C15A 1.480(12) . ? C14A H14C 0.9800 . ? C14A H14D 0.9800 . ? C15A C16A 1.481(12) . ? C15A H15C 0.9800 . ? C15A H15D 0.9800 . ? C16A H16C 0.9800 . ? C16A H16D 0.9800 . ? C17A H17D 0.9700 . ? C17A H17E 0.9700 . ? C17A H17F 0.9700 . ? C18A H18D 0.9700 . ? C18A H18E 0.9700 . ? C18A H18F 0.9700 . ? Cl1 O4 1.391(5) . ? Cl1 O1 1.405(6) . ? Cl1 O2 1.412(5) . ? Cl1 O3 1.444(4) . ? Cl2 O5 1.326(8) . ? Cl2 O7 1.385(6) . ? Cl2 O8 1.397(9) . ? Cl2 O6 1.504(9) . ? Cl3 O12 1.418(5) . ? Cl3 O10 1.426(5) . ? Cl3 O11 1.428(5) . ? Cl3 O9 1.453(5) . ? Cl4 O13 1.281(8) . ? Cl4 O15 1.309(9) . ? Cl4 O14 1.314(10) . ? Cl4 O16 1.357(8) . ? 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 Ni1 N5 110.9(2) . . ? N1 Ni1 N3 151.12(19) . . ? N5 Ni1 N3 97.9(2) . . ? N1 Ni1 N2 79.57(19) . . ? N5 Ni1 N2 105.62(19) . . ? N3 Ni1 N2 94.20(19) . . ? N1 Ni1 N4 79.97(19) . . ? N5 Ni1 N4 97.4(2) . . ? N3 Ni1 N4 95.61(19) . . ? N2 Ni1 N4 153.48(19) . . ? C10 N1 C1 122.0(5) . . ? C10 N1 Ni1 118.2(4) . . ? C1 N1 Ni1 118.0(4) . . ? C3 N2 C2 110.8(5) . . ? C3 N2 Ni1 106.2(3) . . ? C2 N2 Ni1 108.8(4) . . ? C3 N2 H2B 110.3 . . ? C2 N2 H2B 110.3 . . ? Ni1 N2 H2B 110.3 . . ? C5 N3 C6 108.3(5) . . ? C5 N3 C14 108.5(5) . . ? C6 N3 C14 107.5(5) . . ? C5 N3 Ni1 110.9(4) . . ? C6 N3 Ni1 110.0(4) . . ? C14 N3 Ni1 111.4(4) . . ? C8 N4 C9 112.9(5) . . ? C8 N4 Ni1 103.5(4) . . ? C9 N4 Ni1 109.4(3) . . ? C8 N4 H4C 110.3 . . ? C9 N4 H4C 110.3 . . ? Ni1 N4 H4C 110.3 . . ? C16 N5 Ni1 115.5(4) . . ? C16 N5 H5A 108.4 . . ? Ni1 N5 H5A 108.4 . . ? C16 N5 H5B 108.4 . . ? Ni1 N5 H5B 108.4 . . ? H5A N5 H5B 107.5 . . ? N1 C1 C13 120.0(6) . . ? N1 C1 C2 114.2(5) . . ? C13 C1 C2 125.7(6) . . ? N2 C2 C1 108.0(4) . . ? N2 C2 C17 110.0(5) . . ? C1 C2 C17 110.7(5) . . ? N2 C2 H2 109.4 . . ? C1 C2 H2 109.4 . . ? C17 C2 H2 109.4 . . ? N2 C3 C4 113.2(5) . . ? N2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.8 . . ? C3 C4 C5 115.3(5) . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4B 108.4 . . ? C5 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? N3 C5 C4 115.1(5) . . ? N3 C5 H5C 108.5 . . ? C4 C5 H5C 108.5 . . ? N3 C5 H5D 108.5 . . ? C4 C5 H5D 108.5 . . ? H5C C5 H5D 107.5 . . ? N3 C6 C7 115.5(5) . . ? N3 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? N3 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C8 117.3(5) . . ? C6 C7 H7A 108.0 . . ? C8 C7 H7A 108.0 . . ? C6 C7 H7B 108.0 . . ? C8 C7 H7B 108.0 . . ? H7A C7 H7B 107.2 . . ? N4 C8 C7 113.3(5) . . ? N4 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? N4 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N4 C9 C10 108.7(5) . . ? N4 C9 C18 109.4(5) . . ? C10 C9 C18 109.2(5) . . ? N4 C9 H9 109.8 . . ? C10 C9 H9 109.8 . . ? C18 C9 H9 109.8 . . ? N1 C10 C11 120.9(6) . . ? N1 C10 C9 114.7(5) . . ? C11 C10 C9 124.4(6) . . ? C12 C11 C10 117.4(6) . . ? C12 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? C11 C12 C13 121.4(6) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C1 C13 C12 118.2(6) . . ? C1 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? N3 C14 C15 116.0(6) . . ? N3 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? N3 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C14 115.9(6) . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15A 108.3 . . ? C16 C15 H15B 108.3 . . ? C14 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? N5 C16 C15 111.0(5) . . ? N5 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? N5 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C2 C17 H17A 109.5 . . ? C2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C9 C18 H18A 109.5 . . ? C9 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C9 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1A Ni1A N5A 106.5(3) . . ? N1A Ni1A N3A 157.0(3) . . ? N5A Ni1A N3A 96.5(3) . . ? N1A Ni1A N2A 79.9(3) . . ? N5A Ni1A N2A 105.7(4) . . ? N3A Ni1A N2A 95.3(3) . . ? N1A Ni1A N4A 78.8(3) . . ? N5A Ni1A N4A 99.7(5) . . ? N3A Ni1A N4A 96.4(3) . . ? N2A Ni1A N4A 150.5(5) . . ? C10A N1A C1A 122.4(9) . . ? C10A N1A Ni1A 118.1(6) . . ? C1A N1A Ni1A 118.9(8) . . ? C2A N2A C3A 113.1(9) . . ? C2A N2A Ni1A 111.5(6) . . ? C3A N2A Ni1A 105.5(5) . . ? C2A N2A H2AA 108.9 . . ? C3A N2A H2AA 108.9 . . ? Ni1A N2A H2AA 108.9 . . ? C14A N3A C5A 112.0(8) . . ? C14A N3A C6A 103.4(8) . . ? C5A N3A C6A 103.9(8) . . ? C14A N3A Ni1A 114.3(5) . . ? C5A N3A Ni1A 111.3(6) . . ? C6A N3A Ni1A 111.2(5) . . ? C8A N4A C9A 123.1(9) . . ? C8A N4A Ni1A 120.1(9) . . ? C9A N4A Ni1A 112.2(5) . . ? C8A N4A H4AA 97.1 . . ? C9A N4A H4AA 97.1 . . ? Ni1A N4A H4AA 97.1 . . ? C16A N5A Ni1A 121.1(6) . . ? C16A N5A H5A1 107.1 . . ? Ni1A N5A H5A1 107.1 . . ? C16A N5A H5A2 107.1 . . ? Ni1A N5A H5A2 107.1 . . ? H5A1 N5A H5A2 106.8 . . ? N1A C1A C13A 119.6(14) . . ? N1A C1A C2A 113.0(9) . . ? C13A C1A C2A 127.4(13) . . ? N2A C2A C17A 113.6(13) . . ? N2A C2A C1A 108.1(8) . . ? C17A C2A C1A 109.1(11) . . ? N2A C2A H2A 108.6 . . ? C17A C2A H2A 108.6 . . ? C1A C2A H2A 108.6 . . ? N2A C3A C4A 113.9(9) . . ? N2A C3A H3A1 108.8 . . ? C4A C3A H3A1 108.8 . . ? N2A C3A H3A2 108.8 . . ? C4A C3A H3A2 108.8 . . ? H3A1 C3A H3A2 107.7 . . ? C3A C4A C5A 114.5(8) . . ? C3A C4A H4A1 108.6 . . ? C5A C4A H4A1 108.6 . . ? C3A C4A H4A2 108.6 . . ? C5A C4A H4A2 108.6 . . ? H4A1 C4A H4A2 107.6 . . ? N3A C5A C4A 112.7(8) . . ? N3A C5A H5A3 109.0 . . ? C4A C5A H5A3 109.0 . . ? N3A C5A H5A4 109.0 . . ? C4A C5A H5A4 109.0 . . ? H5A3 C5A H5A4 107.8 . . ? C7A C6A N3A 117.9(8) . . ? C7A C6A H6A1 107.8 . . ? N3A C6A H6A1 107.8 . . ? C7A C6A H6A2 107.8 . . ? N3A C6A H6A2 107.8 . . ? H6A1 C6A H6A2 107.2 . . ? C6A C7A C8A 118.4(7) . . ? C6A C7A H7AA 107.7 . . ? C8A C7A H7AA 107.7 . . ? C6A C7A H7AB 107.7 . . ? C8A C7A H7AB 107.7 . . ? H7AA C7A H7AB 107.1 . . ? N4A C8A C7A 126.5(8) . . ? N4A C8A H8AA 105.7 . . ? C7A C8A H8AA 105.7 . . ? N4A C8A H8AB 105.7 . . ? C7A C8A H8AB 105.7 . . ? H8AA C8A H8AB 106.1 . . ? N4A C9A C18A 117.0(12) . . ? N4A C9A C10A 103.3(9) . . ? C18A C9A C10A 109.6(8) . . ? N4A C9A H9A 108.9 . . ? C18A C9A H9A 108.9 . . ? C10A C9A H9A 108.9 . . ? N1A C10A C11A 120.6(11) . . ? N1A C10A C9A 115.2(8) . . ? C11A C10A C9A 124.1(11) . . ? C12A C11A C10A 116.9(14) . . ? C12A C11A H11A 121.5 . . ? C10A C11A H11A 121.5 . . ? C11A C12A C13A 123.8(14) . . ? C11A C12A H12A 118.1 . . ? C13A C12A H12A 118.1 . . ? C1A C13A C12A 116.5(14) . . ? C1A C13A H13A 121.7 . . ? C12A C13A H13A 121.7 . . ? N3A C14A C15A 121.8(8) . . ? N3A C14A H14C 106.9 . . ? C15A C14A H14C 106.9 . . ? N3A C14A H14D 106.9 . . ? C15A C14A H14D 106.9 . . ? H14C C14A H14D 106.7 . . ? C14A C15A C16A 121.4(8) . . ? C14A C15A H15C 107.0 . . ? C16A C15A H15C 107.0 . . ? C14A C15A H15D 107.0 . . ? C16A C15A H15D 107.0 . . ? H15C C15A H15D 106.7 . . ? N5A C16A C15A 117.6(8) . . ? N5A C16A H16C 107.9 . . ? C15A C16A H16C 107.9 . . ? N5A C16A H16D 107.9 . . ? C15A C16A H16D 107.9 . . ? H16C C16A H16D 107.2 . . ? C2A C17A H17D 109.5 . . ? C2A C17A H17E 109.5 . . ? H17D C17A H17E 109.5 . . ? C2A C17A H17F 109.5 . . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? C9A C18A H18D 109.5 . . ? C9A C18A H18E 109.5 . . ? H18D C18A H18E 109.5 . . ? C9A C18A H18F 109.5 . . ? H18D C18A H18F 109.5 . . ? H18E C18A H18F 109.5 . . ? O4 Cl1 O1 108.0(5) . . ? O4 Cl1 O2 110.9(4) . . ? O1 Cl1 O2 109.8(5) . . ? O4 Cl1 O3 109.9(4) . . ? O1 Cl1 O3 108.0(4) . . ? O2 Cl1 O3 110.3(3) . . ? O5 Cl2 O7 114.0(6) . . ? O5 Cl2 O8 117.3(7) . . ? O7 Cl2 O8 109.2(6) . . ? O5 Cl2 O6 105.5(6) . . ? O7 Cl2 O6 105.0(6) . . ? O8 Cl2 O6 104.5(7) . . ? O12 Cl3 O10 109.0(3) . . ? O12 Cl3 O11 109.4(3) . . ? O10 Cl3 O11 110.4(3) . . ? O12 Cl3 O9 109.1(3) . . ? O10 Cl3 O9 109.6(3) . . ? O11 Cl3 O9 109.3(3) . . ? O13 Cl4 O15 111.3(10) . . ? O13 Cl4 O14 102.7(9) . . ? O15 Cl4 O14 105.6(9) . . ? O13 Cl4 O16 115.7(6) . . ? O15 Cl4 O16 109.7(7) . . ? O14 Cl4 O16 111.2(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 N5 Ni1 N1 C10 -95.9(4) . . . . ? N3 Ni1 N1 C10 81.6(6) . . . . ? N2 Ni1 N1 C10 161.3(4) . . . . ? N4 Ni1 N1 C10 -1.8(4) . . . . ? N5 Ni1 N1 C1 99.0(4) . . . . ? N3 Ni1 N1 C1 -83.5(6) . . . . ? N2 Ni1 N1 C1 -3.8(4) . . . . ? N4 Ni1 N1 C1 -166.9(4) . . . . ? N1 Ni1 N2 C3 -97.1(4) . . . . ? N5 Ni1 N2 C3 153.8(4) . . . . ? N3 Ni1 N2 C3 54.4(4) . . . . ? N4 Ni1 N2 C3 -57.1(6) . . . . ? N1 Ni1 N2 C2 22.2(3) . . . . ? N5 Ni1 N2 C2 -86.9(4) . . . . ? N3 Ni1 N2 C2 173.7(3) . . . . ? N4 Ni1 N2 C2 62.2(6) . . . . ? N1 Ni1 N3 C5 25.8(6) . . . . ? N5 Ni1 N3 C5 -156.6(4) . . . . ? N2 Ni1 N3 C5 -50.2(4) . . . . ? N4 Ni1 N3 C5 105.2(4) . . . . ? N1 Ni1 N3 C6 -94.1(5) . . . . ? N5 Ni1 N3 C6 83.6(4) . . . . ? N2 Ni1 N3 C6 -170.0(4) . . . . ? N4 Ni1 N3 C6 -14.7(4) . . . . ? N1 Ni1 N3 C14 146.8(5) . . . . ? N5 Ni1 N3 C14 -35.6(5) . . . . ? N2 Ni1 N3 C14 70.8(4) . . . . ? N4 Ni1 N3 C14 -133.9(4) . . . . ? N1 Ni1 N4 C8 104.4(4) . . . . ? N5 Ni1 N4 C8 -145.5(4) . . . . ? N3 Ni1 N4 C8 -46.8(4) . . . . ? N2 Ni1 N4 C8 64.4(6) . . . . ? N1 Ni1 N4 C9 -16.2(4) . . . . ? N5 Ni1 N4 C9 93.9(4) . . . . ? N3 Ni1 N4 C9 -167.4(4) . . . . ? N2 Ni1 N4 C9 -56.2(6) . . . . ? N1 Ni1 N5 C16 -141.4(4) . . . . ? N3 Ni1 N5 C16 39.8(5) . . . . ? N2 Ni1 N5 C16 -56.8(5) . . . . ? N4 Ni1 N5 C16 136.6(4) . . . . ? C10 N1 C1 C13 0.2(9) . . . . ? Ni1 N1 C1 C13 164.7(4) . . . . ? C10 N1 C1 C2 179.6(5) . . . . ? Ni1 N1 C1 C2 -15.9(6) . . . . ? C3 N2 C2 C1 81.3(6) . . . . ? Ni1 N2 C2 C1 -35.0(5) . . . . ? C3 N2 C2 C17 -157.8(5) . . . . ? Ni1 N2 C2 C17 85.8(5) . . . . ? N1 C1 C2 N2 34.0(7) . . . . ? C13 C1 C2 N2 -146.7(6) . . . . ? N1 C1 C2 C17 -86.4(6) . . . . ? C13 C1 C2 C17 92.9(7) . . . . ? C2 N2 C3 C4 173.7(5) . . . . ? Ni1 N2 C3 C4 -68.3(5) . . . . ? N2 C3 C4 C5 71.1(7) . . . . ? C6 N3 C5 C4 178.5(6) . . . . ? C14 N3 C5 C4 -65.0(7) . . . . ? Ni1 N3 C5 C4 57.7(6) . . . . ? C3 C4 C5 N3 -63.5(8) . . . . ? C5 N3 C6 C7 -59.4(7) . . . . ? C14 N3 C6 C7 -176.4(6) . . . . ? Ni1 N3 C6 C7 62.0(6) . . . . ? N3 C6 C7 C8 -47.3(8) . . . . ? C9 N4 C8 C7 -167.3(5) . . . . ? Ni1 N4 C8 C7 74.5(5) . . . . ? C6 C7 C8 N4 -32.7(8) . . . . ? C8 N4 C9 C10 -85.5(6) . . . . ? Ni1 N4 C9 C10 29.3(5) . . . . ? C8 N4 C9 C18 155.3(5) . . . . ? Ni1 N4 C9 C18 -90.0(5) . . . . ? C1 N1 C10 C11 1.9(9) . . . . ? Ni1 N1 C10 C11 -162.6(5) . . . . ? C1 N1 C10 C9 -175.8(5) . . . . ? Ni1 N1 C10 C9 19.7(6) . . . . ? N4 C9 C10 N1 -32.6(7) . . . . ? C18 C9 C10 N1 86.8(6) . . . . ? N4 C9 C10 C11 149.9(6) . . . . ? C18 C9 C10 C11 -90.7(7) . . . . ? N1 C10 C11 C12 -2.1(9) . . . . ? C9 C10 C11 C12 175.3(6) . . . . ? C10 C11 C12 C13 0.3(9) . . . . ? N1 C1 C13 C12 -1.9(9) . . . . ? C2 C1 C13 C12 178.8(6) . . . . ? C11 C12 C13 C1 1.6(9) . . . . ? C5 N3 C14 C15 174.7(6) . . . . ? C6 N3 C14 C15 -68.4(7) . . . . ? Ni1 N3 C14 C15 52.3(7) . . . . ? N3 C14 C15 C16 -70.5(8) . . . . ? Ni1 N5 C16 C15 -57.0(7) . . . . ? C14 C15 C16 N5 70.4(8) . . . . ? N5A Ni1A N1A C10A -90.1(7) . . . . ? N3A Ni1A N1A C10A 86.7(10) . . . . ? N2A Ni1A N1A C10A 166.3(6) . . . . ? N4A Ni1A N1A C10A 6.9(7) . . . . ? N5A Ni1A N1A C1A 98.9(7) . . . . ? N3A Ni1A N1A C1A -84.3(9) . . . . ? N2A Ni1A N1A C1A -4.7(6) . . . . ? N4A Ni1A N1A C1A -164.2(8) . . . . ? N1A Ni1A N2A C2A 20.9(7) . . . . ? N5A Ni1A N2A C2A -83.6(8) . . . . ? N3A Ni1A N2A C2A 178.1(7) . . . . ? N4A Ni1A N2A C2A 65.3(10) . . . . ? N1A Ni1A N2A C3A -102.3(7) . . . . ? N5A Ni1A N2A C3A 153.3(7) . . . . ? N3A Ni1A N2A C3A 55.0(7) . . . . ? N4A Ni1A N2A C3A -57.9(11) . . . . ? N1A Ni1A N3A C14A 152.4(9) . . . . ? N5A Ni1A N3A C14A -30.7(8) . . . . ? N2A Ni1A N3A C14A 75.9(8) . . . . ? N4A Ni1A N3A C14A -131.3(8) . . . . ? N1A Ni1A N3A C5A 24.2(11) . . . . ? N5A Ni1A N3A C5A -158.8(7) . . . . ? N2A Ni1A N3A C5A -52.3(7) . . . . ? N4A Ni1A N3A C5A 100.6(8) . . . . ? N1A Ni1A N3A C6A -91.1(9) . . . . ? N5A Ni1A N3A C6A 85.9(6) . . . . ? N2A Ni1A N3A C6A -167.6(6) . . . . ? N4A Ni1A N3A C6A -14.7(7) . . . . ? N1A Ni1A N4A C8A 130.5(14) . . . . ? N5A Ni1A N4A C8A -124.5(13) . . . . ? N3A Ni1A N4A C8A -26.7(13) . . . . ? N2A Ni1A N4A C8A 85.9(12) . . . . ? N1A Ni1A N4A C9A -26.2(11) . . . . ? N5A Ni1A N4A C9A 78.9(11) . . . . ? N3A Ni1A N4A C9A 176.6(11) . . . . ? N2A Ni1A N4A C9A -70.8(15) . . . . ? N1A Ni1A N5A C16A -148.1(9) . . . . ? N3A Ni1A N5A C16A 33.1(9) . . . . ? N2A Ni1A N5A C16A -64.3(9) . . . . ? N4A Ni1A N5A C16A 130.7(9) . . . . ? C10A N1A C1A C13A 0.2(14) . . . . ? Ni1A N1A C1A C13A 170.8(8) . . . . ? C10A N1A C1A C2A 177.7(8) . . . . ? Ni1A N1A C1A C2A -11.7(10) . . . . ? C3A N2A C2A C17A -151.2(10) . . . . ? Ni1A N2A C2A C17A 90.1(11) . . . . ? C3A N2A C2A C1A 87.5(9) . . . . ? Ni1A N2A C2A C1A -31.2(10) . . . . ? N1A C1A C2A N2A 28.1(11) . . . . ? C13A C1A C2A N2A -154.7(10) . . . . ? N1A C1A C2A C17A -96.0(11) . . . . ? C13A C1A C2A C17A 81.3(14) . . . . ? C2A N2A C3A C4A 168.4(9) . . . . ? Ni1A N2A C3A C4A -69.4(10) . . . . ? N2A C3A C4A C5A 71.9(12) . . . . ? C14A N3A C5A C4A -71.5(11) . . . . ? C6A N3A C5A C4A 177.5(8) . . . . ? Ni1A N3A C5A C4A 57.8(10) . . . . ? C3A C4A C5A N3A -63.0(12) . . . . ? C14A N3A C6A C7A 175.3(8) . . . . ? C5A N3A C6A C7A -67.5(10) . . . . ? Ni1A N3A C6A C7A 52.3(9) . . . . ? N3A C6A C7A C8A -54.0(13) . . . . ? C9A N4A C8A C7A -169.2(13) . . . . ? Ni1A N4A C8A C7A 37(2) . . . . ? C6A C7A C8A N4A 2(2) . . . . ? C8A N4A C9A C18A 120.5(17) . . . . ? Ni1A N4A C9A C18A -83.6(12) . . . . ? C8A N4A C9A C10A -119.0(16) . . . . ? Ni1A N4A C9A C10A 36.9(13) . . . . ? C1A N1A C10A C11A 1.5(13) . . . . ? Ni1A N1A C10A C11A -169.2(7) . . . . ? C1A N1A C10A C9A -176.1(8) . . . . ? Ni1A N1A C10A C9A 13.3(10) . . . . ? N4A C9A C10A N1A -32.5(13) . . . . ? C18A C9A C10A N1A 92.9(10) . . . . ? N4A C9A C10A C11A 150.0(10) . . . . ? C18A C9A C10A C11A -84.5(12) . . . . ? N1A C10A C11A C12A -1.6(15) . . . . ? C9A C10A C11A C12A 175.8(11) . . . . ? C10A C11A C12A C13A 0(2) . . . . ? N1A C1A C13A C12A -1.6(18) . . . . ? C2A C1A C13A C12A -178.7(11) . . . . ? C11A C12A C13A C1A 2(2) . . . . ? C5A N3A C14A C15A 170.7(11) . . . . ? C6A N3A C14A C15A -78.1(12) . . . . ? Ni1A N3A C14A C15A 42.9(13) . . . . ? N3A C14A C15A C16A -50.5(16) . . . . ? Ni1A N5A C16A C15A -43.0(14) . . . . ? C14A C15A C16A N5A 48.1(15) . . . . ? _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 1.030 _refine_diff_density_min -0.847 _refine_diff_density_rms 0.098 #===END data_[Ni(L2b)](ClO4)2 _database_code_CSD 198024 _audit_creation_method manual _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H33 Cl2 N5 Ni O8' _chemical_formula_weight 577.10 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.745(3) _cell_length_b 16.107(3) _cell_length_c 8.952(3) _cell_angle_alpha 105.17(2) _cell_angle_beta 105.66(2) _cell_angle_gamma 88.86(2) _cell_volume 1303.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.999 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8 _exptl_absorpt_correction_T_max 0.85 _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 AFC5S _diffrn_measurement_method 'omega scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 6 _diffrn_reflns_number 3776 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.1053 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 22.53 _reflns_number_total 3409 _reflns_number_gt 2199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction teXsan _computing_structure_solution SHELXS-97 _computing_structure_refinement SHELXL-97 _computing_publication_material SHELXL-97 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0961P)^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 3409 _refine_ls_number_parameters 307 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.1325 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1848 _refine_ls_wR_factor_gt 0.1532 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.016 _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 0.17653(9) 0.25883(6) 0.05919(11) 0.0517(4) Uani 1 d . . . N1 N -0.0238(6) 0.2786(4) -0.0483(8) 0.0569(16) Uani 1 d . . . N2 N 0.1367(6) 0.3669(4) 0.2344(7) 0.0588(16) Uani 1 d . . . H2C H 0.1754 0.3610 0.3353 0.080 Uiso 1 calc R . . N3 N 0.3934(6) 0.2704(4) 0.1499(8) 0.0625(17) Uani 1 d . . . N4 N 0.1682(7) 0.2082(4) -0.1847(8) 0.0685(18) Uani 1 d . . . H4C H 0.1745 0.2549 -0.2224 0.080 Uiso 1 calc R . . N5 N 0.1544(6) 0.1519(4) 0.1300(8) 0.0653(17) Uani 1 d . . . H5C H 0.0610 0.1415 0.1171 0.080 Uiso 1 calc R . . H5D H 0.1836 0.1072 0.0639 0.080 Uiso 1 calc R . . C1 C -0.0949(8) 0.3395(5) 0.0307(10) 0.060(2) Uani 1 d . . . C2 C -0.0179(8) 0.3790(5) 0.2057(10) 0.067(2) Uani 1 d . . . H2A H -0.0323 0.4410 0.2312 0.080 Uiso 1 calc R . . C3 C 0.2131(9) 0.4392(5) 0.2072(11) 0.074(2) Uani 1 d . . . H3C H 0.1876 0.4939 0.2670 0.080 Uiso 1 calc R . . H3D H 0.1838 0.4374 0.0938 0.080 Uiso 1 calc R . . C4 C 0.3731(8) 0.4322(5) 0.2606(11) 0.078(3) Uani 1 d . . . H4A H 0.4181 0.4865 0.2658 0.080 Uiso 1 calc R . . H4B H 0.3977 0.4257 0.3693 0.080 Uiso 1 calc R . . C5 C 0.4390(8) 0.3608(5) 0.1605(11) 0.075(2) Uani 1 d . . . H5A H 0.4167 0.3677 0.0522 0.080 Uiso 1 calc R . . H5B H 0.5419 0.3680 0.2043 0.080 Uiso 1 calc R . . C6 C 0.4715(8) 0.2103(6) 0.0450(11) 0.083(3) Uani 1 d . . . H6A H 0.5718 0.2289 0.0846 0.080 Uiso 1 calc R . . H6B H 0.4634 0.1534 0.0608 0.080 Uiso 1 calc R . . C7 C 0.4267(9) 0.2013(6) -0.1320(11) 0.082(3) Uani 1 d . . . H7A H 0.4994 0.1716 -0.1780 0.080 Uiso 1 calc R . . H7B H 0.4237 0.2585 -0.1487 0.080 Uiso 1 calc R . . C8 C 0.2844(9) 0.1539(5) -0.2237(10) 0.077(2) Uani 1 d . . . H8A H 0.2744 0.1404 -0.3384 0.080 Uiso 1 calc R . . H8B H 0.2791 0.1003 -0.1949 0.080 Uiso 1 calc R . . C9 C 0.0218(9) 0.1706(6) -0.2648(10) 0.080(3) Uani 1 d . . . H9A H 0.0132 0.1202 -0.2253 0.080 Uiso 1 calc R . . C10 C -0.0798(8) 0.2359(5) -0.2011(11) 0.069(2) Uani 1 d . . . C11 C -0.2101(9) 0.2543(6) -0.2826(12) 0.085(3) Uani 1 d . . . H11A H -0.2490 0.2251 -0.3901 0.080 Uiso 1 calc R . . C12 C -0.2849(9) 0.3170(7) -0.2048(14) 0.090(3) Uani 1 d . . . H12A H -0.3752 0.3291 -0.2597 0.080 Uiso 1 calc R . . C13 C -0.2269(9) 0.3612(6) -0.0480(12) 0.076(2) Uani 1 d . . . H13A H -0.2752 0.4046 0.0043 0.080 Uiso 1 calc R . . C14 C 0.4399(8) 0.2552(6) 0.3112(11) 0.079(2) Uani 1 d . . . H14A H 0.4057 0.3008 0.3850 0.080 Uiso 1 calc R . . H14B H 0.5434 0.2604 0.3464 0.080 Uiso 1 calc R . . C15 C 0.3923(9) 0.1700(6) 0.3266(11) 0.081(3) Uani 1 d . . . H15A H 0.4396 0.1654 0.4341 0.080 Uiso 1 calc R . . H15B H 0.4248 0.1242 0.2514 0.080 Uiso 1 calc R . . C16 C 0.2318(9) 0.1544(6) 0.2963(10) 0.075(2) Uani 1 d . . . H16A H 0.2135 0.1002 0.3176 0.080 Uiso 1 calc R . . H16B H 0.1972 0.2000 0.3696 0.080 Uiso 1 calc R . . C18 C -0.0781(9) 0.3400(5) 0.3160(11) 0.077(2) Uani 1 d . . . H18A H -0.0234 0.3631 0.4257 0.080 Uiso 1 calc R . . H18B H -0.0726 0.2786 0.2861 0.080 Uiso 1 calc R . . H18C H -0.1759 0.3541 0.3050 0.080 Uiso 1 calc R . . C17 C -0.0131(12) 0.1396(8) -0.4396(13) 0.136(4) Uani 1 d . . . H17A H 0.0499 0.0956 -0.4691 0.080 Uiso 1 calc R . . H17B H -0.0022 0.1866 -0.4838 0.080 Uiso 1 calc R . . H17C H -0.1100 0.1164 -0.4811 0.080 Uiso 1 calc R . . Cl1 Cl 0.7321(2) 0.58634(13) 0.2937(2) 0.0658(6) Uani 1 d D . . O11 O 0.7697(7) 0.5285(4) 0.3886(8) 0.103(2) Uani 1 d D . . O12 O 0.8418(7) 0.5967(4) 0.2239(9) 0.113(2) Uani 1 d D . . O13 O 0.6066(8) 0.5553(5) 0.1713(9) 0.141(3) Uani 1 d D . . O14 O 0.7100(10) 0.6661(4) 0.3892(9) 0.145(3) Uani 1 d D . . Cl2 Cl 0.2187(2) -0.07336(14) -0.1122(3) 0.0872(8) Uani 1 d D . . O21 O 0.0933(6) -0.0281(4) -0.1601(10) 0.118(2) Uani 1 d D . . O22 O 0.1852(8) -0.1397(5) -0.0529(12) 0.146(3) Uani 1 d D . . O23 O 0.3212(8) -0.0147(5) 0.0046(12) 0.168(4) Uani 1 d D . . O24 O 0.2750(9) -0.1085(7) -0.2435(10) 0.167(4) Uani 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0421(5) 0.0534(6) 0.0597(6) 0.0134(5) 0.0156(4) 0.0002(4) N1 0.048(4) 0.058(4) 0.062(4) 0.012(3) 0.015(3) 0.003(3) N2 0.048(4) 0.059(4) 0.069(4) 0.013(3) 0.018(3) -0.002(3) N3 0.041(3) 0.080(5) 0.068(4) 0.024(4) 0.014(3) -0.001(3) N4 0.064(4) 0.070(4) 0.072(5) 0.013(4) 0.026(4) -0.001(3) N5 0.052(4) 0.062(4) 0.088(5) 0.024(4) 0.024(4) 0.000(3) C1 0.043(4) 0.055(5) 0.079(6) 0.021(4) 0.010(4) -0.003(4) C2 0.053(5) 0.050(4) 0.093(6) 0.007(4) 0.027(5) 0.005(4) C3 0.073(6) 0.061(5) 0.089(6) 0.009(5) 0.033(5) -0.009(4) C4 0.070(6) 0.068(6) 0.090(6) 0.012(5) 0.020(5) -0.029(5) C5 0.052(5) 0.079(6) 0.099(7) 0.027(5) 0.027(5) -0.010(4) C6 0.043(5) 0.106(7) 0.104(8) 0.035(6) 0.023(5) 0.013(5) C7 0.079(6) 0.092(7) 0.104(8) 0.043(6) 0.056(6) 0.025(5) C8 0.087(7) 0.079(6) 0.074(6) 0.015(5) 0.045(5) 0.008(5) C9 0.068(6) 0.085(6) 0.069(6) -0.003(5) 0.012(5) -0.017(5) C10 0.053(5) 0.068(5) 0.075(6) 0.012(5) 0.007(5) -0.010(4) C11 0.058(6) 0.101(7) 0.079(6) 0.014(6) 0.001(5) -0.012(5) C12 0.047(5) 0.108(8) 0.106(8) 0.034(7) -0.001(6) 0.000(5) C13 0.052(5) 0.075(6) 0.108(8) 0.032(6) 0.027(5) 0.010(4) C14 0.049(5) 0.102(7) 0.081(6) 0.034(5) 0.002(4) -0.002(5) C15 0.069(6) 0.101(7) 0.079(6) 0.042(5) 0.014(5) 0.020(5) C16 0.083(6) 0.076(6) 0.078(6) 0.034(5) 0.028(5) 0.006(5) C18 0.064(5) 0.077(6) 0.093(6) 0.013(5) 0.038(5) -0.002(4) C17 0.109(9) 0.144(11) 0.116(10) -0.004(8) 0.001(7) -0.011(8) Cl1 0.0733(14) 0.0579(13) 0.0638(13) 0.0120(11) 0.0189(11) 0.0013(10) O11 0.128(6) 0.096(5) 0.102(5) 0.052(4) 0.033(4) 0.021(4) O12 0.116(6) 0.117(5) 0.144(6) 0.052(5) 0.079(5) 0.016(4) O13 0.110(6) 0.170(7) 0.124(6) 0.063(6) -0.026(5) -0.062(5) O14 0.236(10) 0.088(5) 0.117(6) 0.014(5) 0.077(6) 0.045(5) Cl2 0.0602(14) 0.0684(15) 0.133(2) 0.0218(15) 0.0316(14) 0.0024(12) O21 0.073(4) 0.103(5) 0.185(8) 0.049(5) 0.037(5) 0.024(4) O22 0.113(6) 0.107(6) 0.247(10) 0.080(6) 0.067(6) -0.003(5) O23 0.105(6) 0.097(6) 0.248(11) -0.007(6) 0.007(7) -0.032(5) O24 0.138(7) 0.256(11) 0.137(7) 0.078(8) 0.070(6) 0.102(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 Ni N1 1.990(6) . ? Ni N5 2.018(6) . ? Ni N3 2.042(6) . ? Ni N4 2.101(6) . ? Ni N2 2.124(6) . ? N1 C10 1.328(10) . ? N1 C1 1.348(9) . ? N2 C2 1.476(9) . ? N2 C3 1.500(9) . ? N2 H2C 0.9100 . ? N3 C14 1.476(10) . ? N3 C5 1.502(9) . ? N3 C6 1.510(10) . ? N4 C9 1.474(9) . ? N4 C8 1.477(9) . ? N4 H4C 0.9100 . ? N5 C16 1.467(10) . ? N5 H5C 0.9000 . ? N5 H5D 0.9000 . ? C1 C13 1.376(10) . ? C1 C2 1.512(11) . ? C2 C18 1.538(10) . ? C2 H2A 0.9800 . ? C3 C4 1.514(11) . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C4 C5 1.510(11) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.494(12) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.509(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C17 1.458(13) . ? C9 C10 1.536(11) . ? C9 H9A 0.9800 . ? C10 C11 1.353(11) . ? C11 C12 1.382(12) . ? C11 H11A 0.9300 . ? C12 C13 1.364(12) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.510(11) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.528(11) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? Cl1 O14 1.393(6) . ? Cl1 O13 1.400(6) . ? Cl1 O11 1.399(6) . ? Cl1 O12 1.408(6) . ? Cl2 O22 1.391(7) . ? Cl2 O23 1.393(7) . ? Cl2 O24 1.410(7) . ? Cl2 O21 1.433(6) . ? 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 Ni N5 102.7(2) . . ? N1 Ni N3 162.9(2) . . ? N5 Ni N3 94.4(2) . . ? N1 Ni N4 78.5(3) . . ? N5 Ni N4 102.5(3) . . ? N3 Ni N4 97.9(2) . . ? N1 Ni N2 79.5(2) . . ? N5 Ni N2 108.2(2) . . ? N3 Ni N2 95.4(2) . . ? N4 Ni N2 145.4(3) . . ? C10 N1 C1 121.6(7) . . ? C10 N1 Ni 118.6(5) . . ? C1 N1 Ni 119.6(5) . . ? C2 N2 C3 111.8(6) . . ? C2 N2 Ni 110.8(4) . . ? C3 N2 Ni 102.0(4) . . ? C2 N2 H2C 110.6 . . ? C3 N2 H2C 110.6 . . ? Ni N2 H2C 110.6 . . ? C14 N3 C5 109.4(7) . . ? C14 N3 C6 107.3(6) . . ? C5 N3 C6 107.3(6) . . ? C14 N3 Ni 112.1(5) . . ? C5 N3 Ni 106.8(5) . . ? C6 N3 Ni 113.9(5) . . ? C9 N4 C8 116.1(7) . . ? C9 N4 Ni 105.8(5) . . ? C8 N4 Ni 117.9(5) . . ? C9 N4 H4C 105.3 . . ? C8 N4 H4C 105.3 . . ? Ni N4 H4C 105.3 . . ? C16 N5 Ni 116.2(5) . . ? C16 N5 H5C 108.2 . . ? Ni N5 H5C 108.2 . . ? C16 N5 H5D 108.2 . . ? Ni N5 H5D 108.2 . . ? H5C N5 H5D 107.4 . . ? N1 C1 C13 120.3(8) . . ? N1 C1 C2 114.6(6) . . ? C13 C1 C2 125.1(8) . . ? N2 C2 C1 110.3(6) . . ? N2 C2 C18 110.4(7) . . ? C1 C2 C18 110.9(6) . . ? N2 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C18 C2 H2A 108.4 . . ? N2 C3 C4 110.7(7) . . ? N2 C3 H3C 109.5 . . ? C4 C3 H3C 109.5 . . ? N2 C3 H3D 109.5 . . ? C4 C3 H3D 109.5 . . ? H3C C3 H3D 108.1 . . ? C5 C4 C3 118.1(7) . . ? C5 C4 H4A 107.8 . . ? C3 C4 H4A 107.8 . . ? C5 C4 H4B 107.8 . . ? C3 C4 H4B 107.8 . . ? H4A C4 H4B 107.1 . . ? N3 C5 C4 116.3(6) . . ? N3 C5 H5A 108.2 . . ? C4 C5 H5A 108.2 . . ? N3 C5 H5B 108.2 . . ? C4 C5 H5B 108.2 . . ? H5A C5 H5B 107.4 . . ? C7 C6 N3 118.6(7) . . ? C7 C6 H6A 107.7 . . ? N3 C6 H6A 107.7 . . ? C7 C6 H6B 107.7 . . ? N3 C6 H6B 107.7 . . ? H6A C6 H6B 107.1 . . ? C6 C7 C8 116.0(7) . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? N4 C8 C7 109.6(7) . . ? N4 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? N4 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C17 C9 N4 115.3(8) . . ? C17 C9 C10 114.7(8) . . ? N4 C9 C10 107.1(6) . . ? C17 C9 H9A 106.3 . . ? N4 C9 H9A 106.3 . . ? C10 C9 H9A 106.3 . . ? N1 C10 C11 120.0(8) . . ? N1 C10 C9 112.0(7) . . ? C11 C10 C9 128.0(8) . . ? C10 C11 C12 119.5(9) . . ? C10 C11 H11A 120.2 . . ? C12 C11 H11A 120.2 . . ? C13 C12 C11 120.4(8) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C1 118.1(8) . . ? C12 C13 H13A 121.0 . . ? C1 C13 H13A 121.0 . . ? N3 C14 C15 116.8(7) . . ? N3 C14 H14A 108.1 . . ? C15 C14 H14A 108.1 . . ? N3 C14 H14B 108.1 . . ? C15 C14 H14B 108.1 . . ? H14A C14 H14B 107.3 . . ? C14 C15 C16 116.1(7) . . ? C14 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15B 108.3 . . ? C16 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? N5 C16 C15 111.3(7) . . ? N5 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? N5 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C9 C17 H17A 109.5 . . ? C9 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C9 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O14 Cl1 O13 109.4(6) . . ? O14 Cl1 O11 109.4(4) . . ? O13 Cl1 O11 109.7(4) . . ? O14 Cl1 O12 108.9(5) . . ? O13 Cl1 O12 109.1(5) . . ? O11 Cl1 O12 110.4(4) . . ? O22 Cl2 O23 111.1(6) . . ? O22 Cl2 O24 109.0(6) . . ? O23 Cl2 O24 108.0(6) . . ? O22 Cl2 O21 109.7(4) . . ? O23 Cl2 O21 108.1(5) . . ? O24 Cl2 O21 110.9(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 22.53 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.511 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.083 #===END data_[Ni(L3c)](ClO4)2 _database_code_CSD 198025 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H34 Cl2 N6 Ni O11' _chemical_formula_weight 652.13 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.144(2) _cell_length_b 14.008(2) _cell_length_c 16.681(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.526(4) _cell_angle_gamma 90.00 _cell_volume 2813.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2442 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 21.84 _exptl_crystal_description arrowhead _exptl_crystal_colour orange _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.944 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 12559 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_sigmaI/netI 0.0766 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 23.34 _reflns_number_total 3890 _reflns_number_gt 2367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0883P)^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 3890 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0994 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1845 _refine_ls_wR_factor_gt 0.1638 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _refine_ls_shift/su_max 0.427 _refine_ls_shift/su_mean 0.019 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 C19 C 0.1331(12) 0.0308(9) 0.1003(8) 0.175(5) Uiso 1 1 d . . . H19A H 0.1965 0.0321 0.1413 0.263 Uiso 1 1 calc R . . H19B H 0.1533 0.0016 0.0523 0.263 Uiso 1 1 calc R . . H19C H 0.0746 -0.0053 0.1194 0.263 Uiso 1 1 calc R . . Ni1 Ni 0.61504(6) 0.20735(5) 0.23585(4) 0.0434(3) Uani 1 1 d . . . Cl1 Cl 0.77681(19) 0.92154(14) 0.14735(14) 0.0830(7) Uani 1 1 d . . . O1 O 0.5746(4) -0.0331(3) -0.1834(3) 0.0748(15) Uani 1 1 d . . . N1 N 0.6396(5) 0.1540(3) 0.3371(3) 0.0483(14) Uani 1 1 d . . . C1 C 0.7375(7) 0.1151(4) 0.3633(4) 0.059(2) Uani 1 1 d . . . Cl2 Cl 0.64017(16) 0.40782(11) 0.85640(12) 0.0660(6) Uani 1 1 d . . . N2 N 0.7663(4) 0.1664(4) 0.2306(3) 0.0551(15) Uani 1 1 d . . . H2C H 0.7594 0.1140 0.1982 0.066 Uiso 1 1 calc R . . C2 C 0.8209(6) 0.1310(5) 0.3090(4) 0.069(2) Uani 1 1 d . . . H2A H 0.8594 0.0717 0.3012 0.083 Uiso 1 1 calc R . . H2B H 0.8752 0.1772 0.3326 0.083 Uiso 1 1 calc R . . O2 O 0.7287(7) 0.8509(5) 0.0985(5) 0.163(3) Uani 1 1 d . . . N3 N 0.5907(4) 0.2577(3) 0.1258(3) 0.0490(14) Uani 1 1 d . . . O3 O 0.7964(6) 1.0044(4) 0.1045(4) 0.125(2) Uani 1 1 d . . . C3 C 0.8443(6) 0.2303(6) 0.1936(5) 0.074(2) Uani 1 1 d . . . H3A H 0.9132 0.1963 0.1901 0.089 Uiso 1 1 calc R . . H3B H 0.8613 0.2855 0.2281 0.089 Uiso 1 1 calc R . . N4 N 0.4620(4) 0.2116(3) 0.2577(3) 0.0535(14) Uani 1 1 d . . . H4C H 0.4339 0.1541 0.2397 0.064 Uiso 1 1 calc R . . C4 C 0.7961(7) 0.2633(6) 0.1102(5) 0.078(2) Uani 1 1 d . . . H4A H 0.8496 0.3042 0.0888 0.094 Uiso 1 1 calc R . . H4B H 0.7840 0.2081 0.0751 0.094 Uiso 1 1 calc R . . O4 O 0.7045(6) 0.9522(5) 0.2042(5) 0.139(3) Uani 1 1 d . . . N5 N 0.5744(5) 0.1200(3) -0.1491(3) 0.0618(16) Uani 1 1 d . . . H5C H 0.5779 0.1783 -0.1647 0.074 Uiso 1 1 calc R . . C5 C 0.6892(6) 0.3162(4) 0.1084(4) 0.061(2) Uani 1 1 d . . . H5A H 0.6715 0.3451 0.0555 0.073 Uiso 1 1 calc R . . H5B H 0.7001 0.3676 0.1477 0.073 Uiso 1 1 calc R . . O5 O 0.8737(5) 0.8888(4) 0.1933(4) 0.127(3) Uani 1 1 d . . . C6 C 0.4940(7) 0.3256(5) 0.1101(4) 0.069(2) Uani 1 1 d . . . H6A H 0.5120 0.3831 0.1414 0.082 Uiso 1 1 calc R . . H6B H 0.4852 0.3434 0.0534 0.082 Uiso 1 1 calc R . . O6 O 0.6040(5) 0.3309(3) 0.8073(3) 0.0940(18) Uani 1 1 d . . . C7 C 0.3850(7) 0.2885(5) 0.1297(5) 0.078(2) Uani 1 1 d . . . H7A H 0.3261 0.3305 0.1060 0.094 Uiso 1 1 calc R . . H7B H 0.3718 0.2258 0.1055 0.094 Uiso 1 1 calc R . . O7 O 0.6686(8) 0.4841(5) 0.8146(4) 0.170(4) Uani 1 1 d . . . C8 C 0.3807(6) 0.2812(5) 0.2188(5) 0.075(2) Uani 1 1 d . . . H8A H 0.3958 0.3434 0.2434 0.090 Uiso 1 1 calc R . . H8B H 0.3066 0.2622 0.2281 0.090 Uiso 1 1 calc R . . O8 O 0.5625(5) 0.4325(4) 0.9108(3) 0.0936(17) Uani 1 1 d . . . C9 C 0.4589(6) 0.2077(5) 0.3447(4) 0.068(2) Uani 1 1 d . . . H9A H 0.3912 0.1765 0.3558 0.081 Uiso 1 1 calc R . . H9B H 0.4599 0.2718 0.3666 0.081 Uiso 1 1 calc R . . O9 O 0.7343(6) 0.3760(6) 0.9107(5) 0.140(3) Uani 1 1 d . . . C10 C 0.5562(7) 0.1540(4) 0.3827(4) 0.0590(19) Uani 1 1 d . . . C11 C 0.5681(8) 0.1100(5) 0.4584(5) 0.079(2) Uani 1 1 d . . . H11 H 0.5110 0.1102 0.4905 0.095 Uiso 1 1 calc R . . C12 C 0.6693(9) 0.0658(5) 0.4836(5) 0.084(3) Uani 1 1 d . . . H12 H 0.6792 0.0338 0.5328 0.101 Uiso 1 1 calc R . . C13 C 0.7542(8) 0.0684(5) 0.4378(5) 0.078(3) Uani 1 1 d . . . H13 H 0.8219 0.0396 0.4559 0.094 Uiso 1 1 calc R . . C14 C 0.5730(5) 0.1715(4) 0.0708(3) 0.0503(17) Uani 1 1 d . . . H14A H 0.5062 0.1391 0.0820 0.060 Uiso 1 1 calc R . . H14B H 0.6347 0.1280 0.0847 0.060 Uiso 1 1 calc R . . C15 C 0.5625(7) 0.1909(4) -0.0192(4) 0.063(2) Uani 1 1 d . . . H15A H 0.4916 0.2212 -0.0367 0.075 Uiso 1 1 calc R . . H15B H 0.6209 0.2344 -0.0303 0.075 Uiso 1 1 calc R . . C16 C 0.5708(7) 0.1012(4) -0.0655(4) 0.071(2) Uani 1 1 d . . . H16A H 0.6373 0.0669 -0.0434 0.085 Uiso 1 1 calc R . . H16B H 0.5073 0.0610 -0.0597 0.085 Uiso 1 1 calc R . . C17 C 0.5728(5) 0.0515(5) -0.2035(4) 0.0527(17) Uani 1 1 d . . . C18 C 0.5724(7) 0.0810(5) -0.2907(4) 0.078(2) Uani 1 1 d . . . H18A H 0.6276 0.0452 -0.3141 0.117 Uiso 1 1 calc R . . H18B H 0.5887 0.1479 -0.2931 0.117 Uiso 1 1 calc R . . H18C H 0.5005 0.0686 -0.3202 0.117 Uiso 1 1 calc R . . N6 N 0.0920(12) 0.1359(11) 0.0807(8) 0.191(5) Uiso 1 1 d . . . O11 O 0.0941(11) 0.2223(10) 0.0899(8) 0.239(5) Uiso 1 1 d . . . O10 O 0.0115(15) 0.1553(12) 0.0284(10) 0.298(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0505(6) 0.0358(5) 0.0434(5) 0.0003(3) 0.0043(4) 0.0014(3) Cl1 0.0891(17) 0.0604(12) 0.0958(16) 0.0147(11) -0.0021(14) 0.0121(11) O1 0.113(4) 0.041(3) 0.073(3) -0.009(2) 0.022(3) -0.008(3) N1 0.057(4) 0.039(3) 0.047(3) -0.004(2) 0.004(3) -0.003(3) C1 0.075(6) 0.050(4) 0.047(4) -0.005(3) -0.008(4) -0.003(4) Cl2 0.0637(14) 0.0458(10) 0.0889(14) -0.0031(9) 0.0120(11) -0.0075(8) N2 0.053(4) 0.063(3) 0.049(3) 0.000(3) 0.005(3) 0.009(3) C2 0.065(5) 0.075(5) 0.063(5) 0.007(4) -0.006(4) 0.016(4) O2 0.174(8) 0.107(5) 0.186(8) -0.035(5) -0.057(6) 0.001(5) N3 0.069(4) 0.031(3) 0.047(3) 0.001(2) 0.007(3) 0.007(2) O3 0.185(7) 0.081(4) 0.113(5) 0.045(4) 0.036(5) 0.039(4) C3 0.054(5) 0.092(6) 0.082(6) -0.007(5) 0.022(4) -0.003(4) N4 0.057(4) 0.044(3) 0.060(4) -0.010(3) 0.009(3) -0.001(2) C4 0.086(7) 0.088(6) 0.065(5) -0.004(4) 0.027(5) -0.028(5) O4 0.136(7) 0.132(6) 0.159(7) 0.008(5) 0.063(5) 0.007(5) N5 0.102(5) 0.035(3) 0.047(3) 0.001(3) 0.006(3) 0.000(3) C5 0.084(6) 0.044(4) 0.054(4) 0.001(3) 0.010(4) -0.014(4) O5 0.108(5) 0.092(4) 0.167(7) 0.029(4) -0.030(5) 0.021(4) C6 0.090(6) 0.046(4) 0.066(5) 0.003(3) -0.004(4) 0.022(4) O6 0.130(5) 0.062(3) 0.091(4) -0.019(3) 0.020(4) -0.022(3) C7 0.078(6) 0.077(5) 0.074(6) -0.002(4) -0.015(5) 0.033(4) O7 0.316(12) 0.082(5) 0.132(6) 0.008(4) 0.102(7) -0.061(6) C8 0.061(5) 0.068(5) 0.094(6) -0.005(4) 0.005(4) 0.020(4) O8 0.091(5) 0.095(4) 0.097(4) -0.012(3) 0.021(4) 0.010(3) C9 0.070(6) 0.070(5) 0.067(5) -0.004(4) 0.024(4) -0.015(4) O9 0.087(5) 0.170(7) 0.158(7) -0.028(5) 0.000(5) 0.024(4) C10 0.079(6) 0.047(4) 0.052(5) -0.006(3) 0.015(4) -0.014(4) C11 0.116(8) 0.071(5) 0.054(5) -0.009(4) 0.026(5) -0.020(5) C12 0.130(9) 0.061(5) 0.058(5) 0.011(4) 0.002(6) -0.014(5) C13 0.109(8) 0.056(5) 0.059(5) 0.002(4) -0.025(5) 0.004(4) C14 0.070(5) 0.030(3) 0.051(4) -0.004(3) 0.010(3) -0.003(3) C15 0.101(6) 0.039(4) 0.047(4) -0.001(3) 0.006(4) -0.003(3) C16 0.120(7) 0.046(4) 0.045(4) 0.000(3) 0.008(4) 0.006(4) C17 0.062(5) 0.044(4) 0.053(4) -0.007(3) 0.010(3) -0.001(3) C18 0.110(7) 0.074(5) 0.051(5) -0.004(4) 0.018(4) 0.020(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 C19 N6 1.576(16) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? Ni1 N1 1.835(5) . ? Ni1 N2 1.937(5) . ? Ni1 N4 1.941(5) . ? Ni1 N3 1.953(5) . ? Cl1 O2 1.364(7) . ? Cl1 O5 1.395(6) . ? Cl1 O3 1.399(6) . ? Cl1 O4 1.439(7) . ? O1 C17 1.231(7) . ? N1 C1 1.328(8) . ? N1 C10 1.344(9) . ? C1 C13 1.396(9) . ? C1 C2 1.462(10) . ? Cl2 O7 1.345(6) . ? Cl2 O6 1.389(5) . ? Cl2 O8 1.435(6) . ? Cl2 O9 1.434(7) . ? N2 C2 1.473(8) . ? N2 C3 1.494(9) . ? N2 H2C 0.9100 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N3 C6 1.508(8) . ? N3 C5 1.509(8) . ? N3 C14 1.515(7) . ? C3 C4 1.509(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N4 C9 1.458(8) . ? N4 C8 1.477(8) . ? N4 H4C 0.9100 . ? C4 C5 1.491(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N5 C17 1.319(7) . ? N5 C16 1.426(8) . ? N5 H5C 0.8600 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.497(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.498(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.472(10) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.395(10) . ? C11 C12 1.391(12) . ? C11 H11 0.9300 . ? C12 C13 1.361(11) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.515(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.485(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.511(9) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N6 O11 1.220(15) . ? N6 O10 1.251(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 N6 C19 H19A 109.6 . . ? N6 C19 H19B 109.4 . . ? H19A C19 H19B 109.5 . . ? N6 C19 H19C 109.3 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 Ni1 N2 83.1(2) . . ? N1 Ni1 N4 83.3(2) . . ? N2 Ni1 N4 162.6(2) . . ? N1 Ni1 N3 177.0(2) . . ? N2 Ni1 N3 95.3(2) . . ? N4 Ni1 N3 97.8(2) . . ? O2 Cl1 O5 110.8(4) . . ? O2 Cl1 O3 112.6(5) . . ? O5 Cl1 O3 111.4(4) . . ? O2 Cl1 O4 111.0(5) . . ? O5 Cl1 O4 106.3(5) . . ? O3 Cl1 O4 104.4(4) . . ? C1 N1 C10 121.5(6) . . ? C1 N1 Ni1 120.0(5) . . ? C10 N1 Ni1 118.5(5) . . ? N1 C1 C13 120.3(8) . . ? N1 C1 C2 113.4(6) . . ? C13 C1 C2 126.3(7) . . ? O7 Cl2 O6 113.2(4) . . ? O7 Cl2 O8 111.8(4) . . ? O6 Cl2 O8 112.1(4) . . ? O7 Cl2 O9 109.7(6) . . ? O6 Cl2 O9 107.2(4) . . ? O8 Cl2 O9 102.2(4) . . ? C2 N2 C3 109.4(6) . . ? C2 N2 Ni1 112.3(4) . . ? C3 N2 Ni1 119.9(4) . . ? C2 N2 H2C 104.6 . . ? C3 N2 H2C 104.6 . . ? Ni1 N2 H2C 104.6 . . ? C1 C2 N2 109.5(6) . . ? C1 C2 H2A 109.8 . . ? N2 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? N2 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C6 N3 C5 104.1(5) . . ? C6 N3 C14 110.6(5) . . ? C5 N3 C14 111.7(5) . . ? C6 N3 Ni1 114.2(4) . . ? C5 N3 Ni1 110.5(4) . . ? C14 N3 Ni1 105.9(3) . . ? N2 C3 C4 111.9(6) . . ? N2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C9 N4 C8 111.0(6) . . ? C9 N4 Ni1 109.7(4) . . ? C8 N4 Ni1 122.7(5) . . ? C9 N4 H4C 103.8 . . ? C8 N4 H4C 103.8 . . ? Ni1 N4 H4C 103.8 . . ? C5 C4 C3 113.8(6) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C17 N5 C16 122.6(5) . . ? C17 N5 H5C 118.7 . . ? C16 N5 H5C 118.7 . . ? C4 C5 N3 115.8(5) . . ? C4 C5 H5A 108.3 . . ? N3 C5 H5A 108.3 . . ? C4 C5 H5B 108.3 . . ? N3 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C7 C6 N3 115.7(6) . . ? C7 C6 H6A 108.4 . . ? N3 C6 H6A 108.3 . . ? C7 C6 H6B 108.4 . . ? N3 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C8 C7 C6 112.8(6) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N4 C8 C7 111.8(6) . . ? N4 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N4 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N4 C9 C10 108.9(6) . . ? N4 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? N4 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N1 C10 C11 121.0(7) . . ? N1 C10 C9 112.2(6) . . ? C11 C10 C9 126.7(8) . . ? C12 C11 C10 116.9(8) . . ? C12 C11 H11 121.5 . . ? C10 C11 H11 121.5 . . ? C13 C12 C11 121.5(8) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C1 118.6(8) . . ? C12 C13 H13 120.7 . . ? C1 C13 H13 120.7 . . ? N3 C14 C15 116.4(5) . . ? N3 C14 H14A 108.2 . . ? C15 C14 H14A 108.2 . . ? N3 C14 H14B 108.2 . . ? C15 C14 H14B 108.2 . . ? H14A C14 H14B 107.3 . . ? C16 C15 C14 111.1(5) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N5 C16 C15 111.4(5) . . ? N5 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? N5 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? O1 C17 N5 121.0(6) . . ? O1 C17 C18 121.5(6) . . ? N5 C17 C18 117.5(6) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O11 N6 O10 82.8(14) . . ? O11 N6 C19 154.1(15) . . ? O10 N6 C19 123.1(16) . . ? 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 N2 Ni1 N1 C1 0.7(4) . . . . ? N4 Ni1 N1 C1 169.8(5) . . . . ? N3 Ni1 N1 C1 58(5) . . . . ? N2 Ni1 N1 C10 -178.2(5) . . . . ? N4 Ni1 N1 C10 -9.1(4) . . . . ? N3 Ni1 N1 C10 -121(5) . . . . ? C10 N1 C1 C13 3.4(9) . . . . ? Ni1 N1 C1 C13 -175.4(5) . . . . ? C10 N1 C1 C2 -173.9(6) . . . . ? Ni1 N1 C1 C2 7.3(7) . . . . ? N1 Ni1 N2 C2 -8.3(4) . . . . ? N4 Ni1 N2 C2 -47.3(9) . . . . ? N3 Ni1 N2 C2 174.2(4) . . . . ? N1 Ni1 N2 C3 -138.8(5) . . . . ? N4 Ni1 N2 C3 -177.8(6) . . . . ? N3 Ni1 N2 C3 43.7(5) . . . . ? N1 C1 C2 N2 -13.3(8) . . . . ? C13 C1 C2 N2 169.5(6) . . . . ? C3 N2 C2 C1 149.3(6) . . . . ? Ni1 N2 C2 C1 13.7(7) . . . . ? N1 Ni1 N3 C6 141(4) . . . . ? N2 Ni1 N3 C6 -161.9(4) . . . . ? N4 Ni1 N3 C6 29.6(5) . . . . ? N1 Ni1 N3 C5 -102(5) . . . . ? N2 Ni1 N3 C5 -44.9(4) . . . . ? N4 Ni1 N3 C5 146.6(4) . . . . ? N1 Ni1 N3 C14 19(5) . . . . ? N2 Ni1 N3 C14 76.2(4) . . . . ? N4 Ni1 N3 C14 -92.3(4) . . . . ? C2 N2 C3 C4 175.9(6) . . . . ? Ni1 N2 C3 C4 -52.4(8) . . . . ? N1 Ni1 N4 C9 21.5(4) . . . . ? N2 Ni1 N4 C9 60.5(9) . . . . ? N3 Ni1 N4 C9 -161.3(4) . . . . ? N1 Ni1 N4 C8 154.4(5) . . . . ? N2 Ni1 N4 C8 -166.6(6) . . . . ? N3 Ni1 N4 C8 -28.3(5) . . . . ? N2 C3 C4 C5 58.7(8) . . . . ? C3 C4 C5 N3 -68.9(8) . . . . ? C6 N3 C5 C4 -173.4(6) . . . . ? C14 N3 C5 C4 -54.1(7) . . . . ? Ni1 N3 C5 C4 63.6(6) . . . . ? C5 N3 C6 C7 -174.9(6) . . . . ? C14 N3 C6 C7 65.0(7) . . . . ? Ni1 N3 C6 C7 -54.3(7) . . . . ? N3 C6 C7 C8 72.1(8) . . . . ? C9 N4 C8 C7 178.3(6) . . . . ? Ni1 N4 C8 C7 45.9(8) . . . . ? C6 C7 C8 N4 -63.8(8) . . . . ? C8 N4 C9 C10 -167.9(6) . . . . ? Ni1 N4 C9 C10 -29.2(6) . . . . ? C1 N1 C10 C11 -2.3(9) . . . . ? Ni1 N1 C10 C11 176.5(5) . . . . ? C1 N1 C10 C9 175.3(5) . . . . ? Ni1 N1 C10 C9 -5.9(7) . . . . ? N4 C9 C10 N1 23.1(7) . . . . ? N4 C9 C10 C11 -159.5(6) . . . . ? N1 C10 C11 C12 -0.6(10) . . . . ? C9 C10 C11 C12 -177.8(7) . . . . ? C10 C11 C12 C13 2.3(11) . . . . ? C11 C12 C13 C1 -1.2(11) . . . . ? N1 C1 C13 C12 -1.7(10) . . . . ? C2 C1 C13 C12 175.3(7) . . . . ? C6 N3 C14 C15 61.2(8) . . . . ? C5 N3 C14 C15 -54.2(7) . . . . ? Ni1 N3 C14 C15 -174.6(5) . . . . ? N3 C14 C15 C16 167.3(6) . . . . ? C17 N5 C16 C15 -174.4(7) . . . . ? C14 C15 C16 N5 -173.0(6) . . . . ? C16 N5 C17 O1 -4.4(11) . . . . ? C16 N5 C17 C18 177.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 23.34 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.977 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.079 #===END data_[Cu(HL2a)](ClO4)3 _database_code_CSD 198026 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H37 Cl3 Cu N6 O12' _chemical_formula_weight 723.45 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' Cl Cl 0.1484 0.1585 '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 9.0975(13) _cell_length_b 11.9637(17) _cell_length_c 13.886(2) _cell_angle_alpha 91.287(3) _cell_angle_beta 94.926(3) _cell_angle_gamma 95.545(4) _cell_volume 1498.0(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 needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 750 _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-2 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.80 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 8549 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5249 _reflns_number_gt 3983 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.1147P)^2^+0.8143P] 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 5249 _refine_ls_number_parameters 414 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1849 _refine_ls_wR_factor_gt 0.1726 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.004 _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 0.16952(6) 0.72258(4) 0.76976(4) 0.0378(2) Uani 1 1 d . . . N1 N 0.2304(5) 0.5713(4) 0.7722(4) 0.0644(13) Uani 1 1 d . . . N2 N 0.2046(6) 0.7036(4) 0.6275(3) 0.0607(12) Uani 1 1 d . . . H2A H 0.2985 0.7344 0.6208 0.073 Uiso 1 1 calc R . . N3 N 0.1570(4) 0.8888(3) 0.7690(3) 0.0491(10) Uani 1 1 d . . . N4 N 0.2196(5) 0.7137(5) 0.9149(3) 0.0671(14) Uani 1 1 d . . . H4C H 0.3158 0.7427 0.9273 0.081 Uiso 1 1 calc R . . N5 N 0.5966(5) 1.0526(4) 0.7087(4) 0.0561(11) Uani 1 1 d . . . H5A H 0.6008 0.9795 0.7174 0.084 Uiso 1 1 calc R . . H5B H 0.6880 1.0875 0.7139 0.084 Uiso 1 1 calc R . . H5C H 0.5528 1.0629 0.6502 0.084 Uiso 1 1 calc R . . N6 N -0.0732(5) 0.6673(4) 0.7584(4) 0.0587(12) Uani 1 1 d . . . C1 C 0.2525(7) 0.5222(5) 0.6893(8) 0.087(3) Uani 1 1 d . . . C2 C 0.1996(9) 0.5813(7) 0.6017(6) 0.092(2) Uani 1 1 d . . . H2 H 0.0953 0.5535 0.5853 0.110 Uiso 1 1 calc R . . C3 C 0.1034(9) 0.7633(8) 0.5618(5) 0.090(2) Uani 1 1 d . . . H3A H 0.0019 0.7324 0.5669 0.108 Uiso 1 1 calc R . . H3B H 0.1261 0.7516 0.4956 0.108 Uiso 1 1 calc R . . C4 C 0.1181(9) 0.8883(7) 0.5863(6) 0.092(3) Uani 1 1 d . . . H4A H 0.2217 0.9167 0.5866 0.111 Uiso 1 1 calc R . . H4B H 0.0635 0.9253 0.5353 0.111 Uiso 1 1 calc R . . C5 C 0.0655(7) 0.9206(5) 0.6795(6) 0.0717(18) Uani 1 1 d . . . H5D H -0.0351 0.8862 0.6817 0.086 Uiso 1 1 calc R . . H5E H 0.0620 1.0014 0.6816 0.086 Uiso 1 1 calc R . . C6 C 0.0826(7) 0.9280(5) 0.8554(6) 0.077(2) Uani 1 1 d . . . H6A H 0.0813 1.0089 0.8531 0.092 Uiso 1 1 calc R . . H6B H -0.0196 0.8951 0.8492 0.092 Uiso 1 1 calc R . . C7 C 0.1510(8) 0.9009(9) 0.9515(6) 0.102(3) Uani 1 1 d . . . H7A H 0.1084 0.9436 1.0004 0.122 Uiso 1 1 calc R . . H7B H 0.2561 0.9257 0.9549 0.122 Uiso 1 1 calc R . . C8 C 0.1328(9) 0.7769(9) 0.9761(5) 0.097(3) Uani 1 1 d . . . H8A H 0.1661 0.7683 1.0436 0.117 Uiso 1 1 calc R . . H8B H 0.0291 0.7482 0.9660 0.117 Uiso 1 1 calc R . . C9 C 0.2134(9) 0.5916(8) 0.9395(7) 0.107(3) Uani 1 1 d . . . H9 H 0.1084 0.5670 0.9440 0.129 Uiso 1 1 calc R . . C10 C 0.2584(7) 0.5267(6) 0.8571(7) 0.090(3) Uani 1 1 d . . . C11 C 0.3119(11) 0.4225(10) 0.8607(13) 0.155(7) Uani 1 1 d . . . H11 H 0.3255 0.3881 0.9198 0.186 Uiso 1 1 calc R . . C12 C 0.3427(13) 0.3730(10) 0.7836(19) 0.187(11) Uani 1 1 d . . . H12 H 0.3873 0.3063 0.7880 0.225 Uiso 1 1 calc R . . C13 C 0.3110(10) 0.4170(7) 0.6928(12) 0.140(5) Uani 1 1 d . . . H13 H 0.3278 0.3784 0.6365 0.168 Uiso 1 1 calc R . . C14 C 0.3150(5) 0.9370(4) 0.7726(4) 0.0511(13) Uani 1 1 d . . . H14A H 0.3595 0.9034 0.7194 0.061 Uiso 1 1 calc R . . H14B H 0.3659 0.9137 0.8320 0.061 Uiso 1 1 calc R . . C15 C 0.3457(7) 1.0645(5) 0.7679(6) 0.076(2) Uani 1 1 d . . . H15A H 0.3076 1.0887 0.7053 0.091 Uiso 1 1 calc R . . H15B H 0.2950 1.1003 0.8171 0.091 Uiso 1 1 calc R . . C16 C 0.5097(7) 1.0996(5) 0.7837(6) 0.0734(19) Uani 1 1 d . . . H16A H 0.5256 1.1810 0.7841 0.088 Uiso 1 1 calc R . . H16B H 0.5465 1.0754 0.8467 0.088 Uiso 1 1 calc R . . C17 C 0.2816(14) 0.5571(11) 0.5162(8) 0.159(5) Uani 1 1 d . . . H17A H 0.3861 0.5742 0.5328 0.238 Uiso 1 1 calc R . . H17B H 0.2501 0.6024 0.4636 0.238 Uiso 1 1 calc R . . H17C H 0.2612 0.4790 0.4973 0.238 Uiso 1 1 calc R . . C18 C 0.2907(18) 0.5677(14) 1.0343(9) 0.213(8) Uani 1 1 d . . . H18A H 0.2958 0.4882 1.0390 0.320 Uiso 1 1 calc R . . H18B H 0.2370 0.5940 1.0855 0.320 Uiso 1 1 calc R . . H18C H 0.3892 0.6055 1.0398 0.320 Uiso 1 1 calc R . . C19 C -0.1850(6) 0.6218(4) 0.7445(4) 0.0501(12) Uani 1 1 d . . . C20 C -0.3301(7) 0.5601(5) 0.7269(5) 0.0651(15) Uani 1 1 d . . . H20A H -0.3212 0.4812 0.7323 0.098 Uiso 1 1 calc R . . H20B H -0.3720 0.5746 0.6631 0.098 Uiso 1 1 calc R . . H20C H -0.3934 0.5837 0.7738 0.098 Uiso 1 1 calc R . . Cl1 Cl 0.60778(17) 0.82213(12) 0.53230(10) 0.0579(4) Uani 1 1 d . . . O1 O 0.7058(11) 0.9189(6) 0.5480(7) 0.186(4) Uani 1 1 d . . . O2 O 0.6950(9) 0.7346(7) 0.5380(5) 0.147(3) Uani 1 1 d . . . O3 O 0.5362(12) 0.8113(10) 0.4433(5) 0.212(5) Uani 1 1 d . . . O4 O 0.5209(7) 0.8197(5) 0.6108(4) 0.121(2) Uani 1 1 d . . . Cl2 Cl 0.90894(18) 0.26859(14) 0.73716(11) 0.0674(4) Uani 1 1 d . . . O5 O 0.7670(14) 0.2894(11) 0.7750(11) 0.107(3) Uani 0.458(6) 1 d P A 1 O8 O 1.0172(14) 0.2481(15) 0.8130(9) 0.119(6) Uani 0.458(6) 1 d P A 1 O7 O 0.9534(12) 0.3581(9) 0.6800(8) 0.081(3) Uani 0.458(6) 1 d P A 1 O6 O 0.8741(13) 0.1705(9) 0.6804(9) 0.093(4) Uani 0.458(6) 1 d P A 1 O5B O 0.7684(12) 0.2856(9) 0.6877(9) 0.107(3) Uani 0.542(6) 1 d P A 2 O8B O 1.0245(13) 0.2521(14) 0.6711(8) 0.133(6) Uani 0.542(6) 1 d P A 2 O6B O 0.8870(10) 0.1645(7) 0.7823(7) 0.079(3) Uani 0.542(6) 1 d P A 2 O7B O 0.9582(12) 0.3543(9) 0.8067(8) 0.101(4) Uani 0.542(6) 1 d P A 2 Cl3 Cl 0.63713(14) 0.81328(11) 0.92458(10) 0.0556(4) Uani 1 1 d . . . O9 O 0.5541(7) 0.7178(5) 0.8844(6) 0.142(3) Uani 1 1 d . . . O10 O 0.6830(5) 0.8817(5) 0.8489(4) 0.0932(16) Uani 1 1 d . . . O11 O 0.7641(6) 0.7912(6) 0.9828(5) 0.130(3) Uani 1 1 d . . . O12 O 0.5412(5) 0.8689(5) 0.9802(4) 0.0991(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0357(3) 0.0375(3) 0.0414(3) 0.0033(2) 0.0061(2) 0.0074(2) N1 0.043(3) 0.043(3) 0.109(4) 0.010(3) 0.012(3) 0.005(2) N2 0.059(3) 0.073(3) 0.049(3) -0.011(2) 0.014(2) -0.003(2) N3 0.034(2) 0.039(2) 0.075(3) -0.0015(19) 0.005(2) 0.0085(17) N4 0.041(3) 0.115(4) 0.046(3) 0.016(3) 0.007(2) 0.011(3) N5 0.044(3) 0.047(2) 0.078(3) 0.007(2) 0.011(2) 0.0005(19) N6 0.040(3) 0.057(3) 0.078(3) 0.005(2) 0.001(2) 0.005(2) C1 0.049(4) 0.040(3) 0.172(8) -0.027(4) 0.017(4) 0.004(3) C2 0.093(6) 0.082(5) 0.101(6) -0.048(5) 0.012(5) 0.016(4) C3 0.087(5) 0.135(7) 0.044(3) 0.017(4) -0.007(3) -0.004(5) C4 0.070(5) 0.117(7) 0.092(5) 0.065(5) -0.003(4) 0.013(4) C5 0.052(4) 0.053(4) 0.112(6) 0.023(3) -0.001(4) 0.018(3) C6 0.044(3) 0.061(4) 0.129(6) -0.030(4) 0.034(4) 0.010(3) C7 0.050(4) 0.173(9) 0.081(5) -0.071(6) 0.013(4) 0.017(5) C8 0.070(5) 0.175(9) 0.050(4) -0.005(5) 0.021(3) 0.016(5) C9 0.068(5) 0.141(8) 0.123(7) 0.099(6) 0.019(5) 0.031(5) C10 0.046(4) 0.076(5) 0.154(8) 0.065(5) 0.023(4) 0.015(3) C11 0.069(6) 0.094(8) 0.31(2) 0.122(11) 0.032(9) 0.024(6) C12 0.063(7) 0.061(7) 0.44(3) 0.062(11) 0.001(11) 0.022(5) C13 0.060(5) 0.057(5) 0.300(17) -0.070(7) 0.030(7) -0.003(4) C14 0.035(3) 0.039(3) 0.081(4) -0.004(2) 0.011(2) 0.009(2) C15 0.050(3) 0.040(3) 0.140(6) -0.006(3) 0.026(4) 0.008(2) C16 0.053(4) 0.042(3) 0.126(6) -0.015(3) 0.026(4) -0.001(3) C17 0.162(11) 0.183(12) 0.140(9) -0.075(8) 0.031(8) 0.059(9) C18 0.232(17) 0.32(2) 0.110(9) 0.092(11) 0.011(10) 0.143(16) C19 0.044(3) 0.045(3) 0.061(3) -0.001(2) 0.006(2) 0.005(2) C20 0.056(4) 0.067(4) 0.069(4) -0.004(3) 0.005(3) -0.008(3) Cl1 0.0649(9) 0.0611(8) 0.0524(8) 0.0107(6) 0.0168(6) 0.0182(7) O1 0.255(11) 0.109(6) 0.203(8) -0.016(5) 0.147(8) -0.036(6) O2 0.169(7) 0.171(7) 0.117(5) -0.012(5) 0.000(5) 0.105(6) O3 0.247(11) 0.314(13) 0.086(5) -0.019(6) -0.060(6) 0.154(10) O4 0.118(5) 0.126(5) 0.120(4) -0.039(4) 0.077(4) -0.031(4) Cl2 0.0618(10) 0.0793(11) 0.0564(8) 0.0021(7) 0.0045(7) -0.0163(8) O5 0.077(5) 0.111(6) 0.126(7) 0.017(6) -0.014(6) -0.004(4) O8 0.078(8) 0.187(16) 0.083(8) 0.038(9) -0.008(7) -0.019(9) O7 0.066(7) 0.072(7) 0.097(8) 0.025(6) 0.003(6) -0.023(5) O6 0.091(8) 0.080(7) 0.108(9) -0.010(6) 0.037(7) -0.016(6) O5B 0.077(5) 0.111(6) 0.126(7) 0.017(6) -0.014(6) -0.004(4) O8B 0.089(8) 0.218(16) 0.081(7) -0.035(8) 0.031(6) -0.053(9) O6B 0.074(6) 0.065(5) 0.095(7) 0.010(4) -0.007(5) 0.002(4) O7B 0.089(7) 0.077(7) 0.130(9) -0.027(6) 0.011(6) -0.026(6) Cl3 0.0412(7) 0.0569(8) 0.0714(9) 0.0038(6) 0.0148(6) 0.0091(6) O9 0.100(5) 0.086(4) 0.239(8) -0.069(5) 0.064(5) -0.025(3) O10 0.069(3) 0.122(4) 0.095(4) 0.048(3) 0.018(3) 0.023(3) O11 0.063(3) 0.188(7) 0.152(6) 0.098(5) 0.021(3) 0.042(4) O12 0.066(3) 0.146(5) 0.088(3) -0.039(3) 0.021(3) 0.025(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.943(5) . ? Cu1 N3 2.003(4) . ? Cu1 N4 2.035(5) . ? Cu1 N2 2.039(4) . ? Cu1 N6 2.235(5) . ? N1 C1 1.319(10) . ? N1 C10 1.321(9) . ? N2 C3 1.484(9) . ? N2 C2 1.494(8) . ? N2 H2A 0.9100 . ? N3 C14 1.492(6) . ? N3 C5 1.513(8) . ? N3 C6 1.514(7) . ? N4 C8 1.456(9) . ? N4 C9 1.504(10) . ? N4 H4C 0.9100 . ? N5 C16 1.492(7) . ? N5 H5A 0.8900 . ? N5 H5B 0.8900 . ? N5 H5C 0.8900 . ? N6 C19 1.105(6) . ? C1 C13 1.414(12) . ? C1 C2 1.488(12) . ? C2 C17 1.493(12) . ? C2 H2 0.9800 . ? C3 C4 1.517(11) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.473(11) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5D 0.9700 . ? C5 H5E 0.9700 . ? C6 C7 1.479(11) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.526(12) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.477(13) . ? C9 C18 1.485(13) . ? C9 H9 0.9800 . ? C10 C11 1.382(13) . ? C11 C12 1.28(2) . ? C11 H11 0.9300 . ? C12 C13 1.40(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.528(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.506(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.447(8) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? Cl1 O3 1.344(7) . ? Cl1 O2 1.374(6) . ? Cl1 O1 1.392(8) . ? Cl1 O4 1.399(5) . ? Cl2 O6 1.394(11) . ? Cl2 O7 1.397(9) . ? Cl2 O7B 1.406(9) . ? Cl2 O6B 1.412(8) . ? Cl2 O8 1.421(13) . ? Cl2 O5B 1.433(11) . ? Cl2 O5 1.476(15) . ? Cl2 O8B 1.478(11) . ? Cl3 O9 1.385(6) . ? Cl3 O11 1.402(6) . ? Cl3 O10 1.413(5) . ? Cl3 O12 1.416(5) . ? 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 N3 166.80(18) . . ? N1 Cu1 N4 81.5(2) . . ? N3 Cu1 N4 96.2(2) . . ? N1 Cu1 N2 81.2(2) . . ? N3 Cu1 N2 96.5(2) . . ? N4 Cu1 N2 155.3(2) . . ? N1 Cu1 N6 94.94(18) . . ? N3 Cu1 N6 98.26(17) . . ? N4 Cu1 N6 100.51(19) . . ? N2 Cu1 N6 98.5(2) . . ? C1 N1 C10 123.5(7) . . ? C1 N1 Cu1 118.2(5) . . ? C10 N1 Cu1 118.2(5) . . ? C3 N2 C2 112.8(6) . . ? C3 N2 Cu1 113.3(4) . . ? C2 N2 Cu1 109.3(4) . . ? C3 N2 H2A 107.0 . . ? C2 N2 H2A 107.0 . . ? Cu1 N2 H2A 107.0 . . ? C14 N3 C5 112.8(4) . . ? C14 N3 C6 111.6(4) . . ? C5 N3 C6 107.0(5) . . ? C14 N3 Cu1 103.8(3) . . ? C5 N3 Cu1 110.7(3) . . ? C6 N3 Cu1 111.1(4) . . ? C8 N4 C9 112.2(6) . . ? C8 N4 Cu1 116.1(4) . . ? C9 N4 Cu1 108.0(5) . . ? C8 N4 H4C 106.7 . . ? C9 N4 H4C 106.7 . . ? Cu1 N4 H4C 106.7 . . ? C16 N5 H5A 109.5 . . ? C16 N5 H5B 109.5 . . ? H5A N5 H5B 109.5 . . ? C16 N5 H5C 109.5 . . ? H5A N5 H5C 109.5 . . ? H5B N5 H5C 109.5 . . ? C19 N6 Cu1 166.3(5) . . ? N1 C1 C13 117.7(10) . . ? N1 C1 C2 114.7(6) . . ? C13 C1 C2 127.4(9) . . ? C1 C2 C17 112.7(8) . . ? C1 C2 N2 108.2(6) . . ? C17 C2 N2 113.7(8) . . ? C1 C2 H2 107.3 . . ? C17 C2 H2 107.3 . . ? N2 C2 H2 107.3 . . ? N2 C3 C4 111.4(6) . . ? N2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 115.7(6) . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4B 108.4 . . ? C3 C4 H4B 108.4 . . ? H4A C4 H4B 107.4 . . ? C4 C5 N3 115.9(5) . . ? C4 C5 H5D 108.3 . . ? N3 C5 H5D 108.3 . . ? C4 C5 H5E 108.3 . . ? N3 C5 H5E 108.3 . . ? H5D C5 H5E 107.4 . . ? C7 C6 N3 116.1(5) . . ? C7 C6 H6A 108.3 . . ? N3 C6 H6A 108.3 . . ? C7 C6 H6B 108.3 . . ? N3 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C6 C7 C8 115.3(6) . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7B 108.4 . . ? C8 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? N4 C8 C7 109.5(6) . . ? N4 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? N4 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C10 C9 C18 114.0(9) . . ? C10 C9 N4 109.0(5) . . ? C18 C9 N4 115.4(11) . . ? C10 C9 H9 105.9 . . ? C18 C9 H9 105.9 . . ? N4 C9 H9 105.9 . . ? N1 C10 C11 119.1(11) . . ? N1 C10 C9 114.2(6) . . ? C11 C10 C9 126.4(10) . . ? C12 C11 C10 120.5(15) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 121.3(11) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C12 C13 C1 117.7(12) . . ? C12 C13 H13 121.2 . . ? C1 C13 H13 121.2 . . ? N3 C14 C15 117.6(4) . . ? N3 C14 H14A 107.9 . . ? C15 C14 H14A 107.9 . . ? N3 C14 H14B 107.9 . . ? C15 C14 H14B 107.9 . . ? H14A C14 H14B 107.2 . . ? C16 C15 C14 110.6(5) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N5 C16 C15 113.5(5) . . ? N5 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? N5 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C2 C17 H17A 109.5 . . ? C2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C9 C18 H18A 109.5 . . ? C9 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C9 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N6 C19 C20 178.8(6) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 Cl1 O2 104.9(5) . . ? O3 Cl1 O1 114.5(7) . . ? O2 Cl1 O1 105.3(6) . . ? O3 Cl1 O4 117.2(6) . . ? O2 Cl1 O4 109.2(5) . . ? O1 Cl1 O4 105.1(4) . . ? O6 Cl2 O7 110.4(7) . . ? O6 Cl2 O7B 169.0(8) . . ? O7 Cl2 O7B 77.7(7) . . ? O6 Cl2 O6B 60.5(6) . . ? O7 Cl2 O6B 166.3(7) . . ? O7B Cl2 O6B 110.1(6) . . ? O6 Cl2 O8 108.6(10) . . ? O7 Cl2 O8 113.5(7) . . ? O7B Cl2 O8 60.7(8) . . ? O6B Cl2 O8 64.0(7) . . ? O6 Cl2 O5B 77.0(7) . . ? O7 Cl2 O5B 80.6(6) . . ? O7B Cl2 O5B 112.3(7) . . ? O6B Cl2 O5B 105.6(6) . . ? O8 Cl2 O5B 160.3(8) . . ? O6 Cl2 O5 103.8(7) . . ? O7 Cl2 O5 108.8(8) . . ? O7B Cl2 O5 79.7(7) . . ? O6B Cl2 O5 84.0(6) . . ? O8 Cl2 O5 111.4(8) . . ? O5B Cl2 O5 49.3(6) . . ? O6 Cl2 O8B 68.6(6) . . ? O7 Cl2 O8B 62.2(7) . . ? O7B Cl2 O8B 110.8(6) . . ? O6B Cl2 O8B 104.2(8) . . ? O8 Cl2 O8B 86.1(8) . . ? O5B Cl2 O8B 113.3(8) . . ? O5 Cl2 O8B 162.5(8) . . ? O9 Cl3 O11 114.0(5) . . ? O9 Cl3 O10 108.6(5) . . ? O11 Cl3 O10 107.9(3) . . ? O9 Cl3 O12 106.1(4) . . ? O11 Cl3 O12 110.0(4) . . ? O10 Cl3 O12 110.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 N1 C1 -86.7(11) . . . . ? N4 Cu1 N1 C1 -167.9(5) . . . . ? N2 Cu1 N1 C1 -5.6(4) . . . . ? N6 Cu1 N1 C1 92.2(5) . . . . ? N3 Cu1 N1 C10 88.2(10) . . . . ? N4 Cu1 N1 C10 7.1(5) . . . . ? N2 Cu1 N1 C10 169.3(5) . . . . ? N6 Cu1 N1 C10 -92.9(5) . . . . ? N1 Cu1 N2 C3 147.2(5) . . . . ? N3 Cu1 N2 C3 -46.0(5) . . . . ? N4 Cu1 N2 C3 -166.6(5) . . . . ? N6 Cu1 N2 C3 53.4(5) . . . . ? N1 Cu1 N2 C2 20.4(4) . . . . ? N3 Cu1 N2 C2 -172.7(5) . . . . ? N4 Cu1 N2 C2 66.6(7) . . . . ? N6 Cu1 N2 C2 -73.3(5) . . . . ? N1 Cu1 N3 C14 1.0(11) . . . . ? N4 Cu1 N3 C14 80.4(4) . . . . ? N2 Cu1 N3 C14 -78.4(4) . . . . ? N6 Cu1 N3 C14 -177.9(3) . . . . ? N1 Cu1 N3 C5 122.3(10) . . . . ? N4 Cu1 N3 C5 -158.3(4) . . . . ? N2 Cu1 N3 C5 42.9(4) . . . . ? N6 Cu1 N3 C5 -56.7(4) . . . . ? N1 Cu1 N3 C6 -119.0(10) . . . . ? N4 Cu1 N3 C6 -39.6(4) . . . . ? N2 Cu1 N3 C6 161.6(4) . . . . ? N6 Cu1 N3 C6 62.0(4) . . . . ? N1 Cu1 N4 C8 -148.5(6) . . . . ? N3 Cu1 N4 C8 44.6(6) . . . . ? N2 Cu1 N4 C8 165.3(5) . . . . ? N6 Cu1 N4 C8 -55.0(6) . . . . ? N1 Cu1 N4 C9 -21.6(4) . . . . ? N3 Cu1 N4 C9 171.5(4) . . . . ? N2 Cu1 N4 C9 -67.8(7) . . . . ? N6 Cu1 N4 C9 71.9(4) . . . . ? N1 Cu1 N6 C19 -27(2) . . . . ? N3 Cu1 N6 C19 152(2) . . . . ? N4 Cu1 N6 C19 -110(2) . . . . ? N2 Cu1 N6 C19 54(2) . . . . ? C10 N1 C1 C13 -0.9(10) . . . . ? Cu1 N1 C1 C13 173.7(5) . . . . ? C10 N1 C1 C2 174.1(6) . . . . ? Cu1 N1 C1 C2 -11.2(8) . . . . ? N1 C1 C2 C17 154.3(7) . . . . ? C13 C1 C2 C17 -31.3(12) . . . . ? N1 C1 C2 N2 27.7(9) . . . . ? C13 C1 C2 N2 -157.9(7) . . . . ? C3 N2 C2 C1 -157.5(6) . . . . ? Cu1 N2 C2 C1 -30.4(7) . . . . ? C3 N2 C2 C17 76.6(10) . . . . ? Cu1 N2 C2 C17 -156.4(7) . . . . ? C2 N2 C3 C4 -176.6(6) . . . . ? Cu1 N2 C3 C4 58.6(7) . . . . ? N2 C3 C4 C5 -67.9(8) . . . . ? C3 C4 C5 N3 69.2(8) . . . . ? C14 N3 C5 C4 57.7(7) . . . . ? C6 N3 C5 C4 -179.2(6) . . . . ? Cu1 N3 C5 C4 -58.1(6) . . . . ? C14 N3 C6 C7 -58.7(7) . . . . ? C5 N3 C6 C7 177.5(6) . . . . ? Cu1 N3 C6 C7 56.6(7) . . . . ? N3 C6 C7 C8 -70.6(8) . . . . ? C9 N4 C8 C7 176.7(6) . . . . ? Cu1 N4 C8 C7 -58.5(7) . . . . ? C6 C7 C8 N4 68.8(8) . . . . ? C8 N4 C9 C10 161.1(6) . . . . ? Cu1 N4 C9 C10 31.9(7) . . . . ? C8 N4 C9 C18 -69.1(10) . . . . ? Cu1 N4 C9 C18 161.7(8) . . . . ? C1 N1 C10 C11 -0.8(10) . . . . ? Cu1 N1 C10 C11 -175.5(6) . . . . ? C1 N1 C10 C9 -175.0(6) . . . . ? Cu1 N1 C10 C9 10.3(8) . . . . ? C18 C9 C10 N1 -158.8(9) . . . . ? N4 C9 C10 N1 -28.3(9) . . . . ? C18 C9 C10 C11 27.5(14) . . . . ? N4 C9 C10 C11 158.1(8) . . . . ? N1 C10 C11 C12 4.4(16) . . . . ? C9 C10 C11 C12 177.8(11) . . . . ? C10 C11 C12 C13 -6(2) . . . . ? C11 C12 C13 C1 4.1(19) . . . . ? N1 C1 C13 C12 -0.6(12) . . . . ? C2 C1 C13 C12 -174.9(9) . . . . ? C5 N3 C14 C15 57.2(7) . . . . ? C6 N3 C14 C15 -63.3(7) . . . . ? Cu1 N3 C14 C15 177.0(5) . . . . ? N3 C14 C15 C16 173.6(6) . . . . ? C14 C15 C16 N5 61.8(8) . . . . ? Cu1 N6 C19 C20 46(33) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.221 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.099 #===END data_[Cu(L2a)](ClO4)2 _database_code_CSD 198027 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H36 Cl2 Cu N6 O8' _chemical_formula_weight 622.99 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' Cl Cl 0.1484 0.1585 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.431(7) _cell_length_b 8.861(5) _cell_length_c 28.031(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.766(7) _cell_angle_gamma 90.00 _cell_volume 2779(3) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1300 _exptl_absorpt_coefficient_mu 1.031 _exptl_absorpt_correction_type 'Semi-empirical, SADABS' _exptl_absorpt_correction_T_min 0.727409 _exptl_absorpt_correction_T_max 0.942188 _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-3 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 14389 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 0.74 _diffrn_reflns_theta_max 24.74 _reflns_number_total 4906 _reflns_number_gt 4663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.0682P)^2^+1.4646P] 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 4906 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.46106(4) 0.33400(5) 0.143493(16) 0.03202(13) Uani 1 1 d . . . N1 N 0.2930(3) 0.2683(4) 0.12368(12) 0.0412(8) Uani 1 1 d . . . N2 N 0.4823(3) 0.1148(4) 0.12032(13) 0.0468(8) Uani 1 1 d . . . H2B H 0.4738 0.0564 0.1465 0.056 Uiso 1 1 calc R . . N3 N 0.6295(3) 0.3565(4) 0.18358(11) 0.0360(7) Uani 1 1 d . . . N4 N 0.3842(3) 0.4628(4) 0.19148(11) 0.0417(8) Uani 1 1 d . . . H4C H 0.4192 0.5567 0.1954 0.050 Uiso 1 1 calc R . . N5 N 0.4957(4) 0.4827(4) 0.08675(13) 0.0500(9) Uani 1 1 d . . . H5A H 0.5422 0.4333 0.0690 0.060 Uiso 1 1 calc R . . H5B H 0.4252 0.5053 0.0664 0.060 Uiso 1 1 calc R . . C1 C 0.2691(4) 0.1420(5) 0.09723(16) 0.0484(10) Uani 1 1 d . . . C2 C 0.3750(4) 0.0743(5) 0.08161(16) 0.0503(11) Uani 1 1 d . . . H2A H 0.3660 -0.0369 0.0804 0.060 Uiso 1 1 calc R . . C3 C 0.5971(4) 0.0688(5) 0.11070(18) 0.0525(11) Uani 1 1 d . . . H3A H 0.6122 0.1228 0.0821 0.063 Uiso 1 1 calc R . . H3B H 0.5953 -0.0395 0.1035 0.063 Uiso 1 1 calc R . . C4 C 0.6968(4) 0.1011(5) 0.15374(18) 0.0545(12) Uani 1 1 d . . . H4A H 0.7703 0.0540 0.1479 0.065 Uiso 1 1 calc R . . H4B H 0.6774 0.0537 0.1827 0.065 Uiso 1 1 calc R . . C5 C 0.7208(4) 0.2685(5) 0.16418(18) 0.0524(11) Uani 1 1 d . . . H5C H 0.7970 0.2775 0.1875 0.063 Uiso 1 1 calc R . . H5D H 0.7313 0.3168 0.1339 0.063 Uiso 1 1 calc R . . C6 C 0.6264(4) 0.3010(5) 0.23410(14) 0.0470(10) Uani 1 1 d . . . H6A H 0.7077 0.3064 0.2537 0.056 Uiso 1 1 calc R . . H6B H 0.6033 0.1943 0.2317 0.056 Uiso 1 1 calc R . . C7 C 0.5444(4) 0.3824(5) 0.26131(14) 0.0489(10) Uani 1 1 d . . . H7A H 0.5698 0.4881 0.2650 0.059 Uiso 1 1 calc R . . H7B H 0.5555 0.3388 0.2941 0.059 Uiso 1 1 calc R . . C8 C 0.4110(4) 0.3791(5) 0.23854(15) 0.0475(10) Uani 1 1 d . . . H8A H 0.3848 0.2741 0.2330 0.057 Uiso 1 1 calc R . . H8B H 0.3661 0.4244 0.2612 0.057 Uiso 1 1 calc R . . C9 C 0.2518(4) 0.4787(6) 0.17251(16) 0.0514(11) Uani 1 1 d . . . H9A H 0.2110 0.4823 0.2004 0.062 Uiso 1 1 calc R . . C10 C 0.2094(3) 0.3407(6) 0.14186(15) 0.0473(10) Uani 1 1 d . . . C11 C 0.0916(4) 0.2904(8) 0.13137(18) 0.0704(16) Uani 1 1 d . . . H11A H 0.0314 0.3415 0.1433 0.084 Uiso 1 1 calc R . . C12 C 0.0662(5) 0.1628(8) 0.1029(2) 0.0764(17) Uani 1 1 d . . . H12A H -0.0130 0.1280 0.0946 0.092 Uiso 1 1 calc R . . C13 C 0.1541(5) 0.0857(7) 0.08625(19) 0.0642(13) Uani 1 1 d . . . H13A H 0.1365 -0.0032 0.0679 0.077 Uiso 1 1 calc R . . C14 C 0.6704(4) 0.5187(5) 0.18730(16) 0.0458(10) Uani 1 1 d . . . H14A H 0.7504 0.5226 0.2081 0.055 Uiso 1 1 calc R . . H14B H 0.6169 0.5760 0.2038 0.055 Uiso 1 1 calc R . . C15 C 0.6749(4) 0.5976(5) 0.13961(17) 0.0546(11) Uani 1 1 d . . . H15A H 0.7252 0.5376 0.1224 0.066 Uiso 1 1 calc R . . H15B H 0.7141 0.6956 0.1472 0.066 Uiso 1 1 calc R . . C16 C 0.5554(5) 0.6238(5) 0.10536(17) 0.0594(12) Uani 1 1 d . . . H16A H 0.5031 0.6805 0.1226 0.071 Uiso 1 1 calc R . . H16B H 0.5679 0.6854 0.0778 0.071 Uiso 1 1 calc R . . C17 C 0.3810(5) 0.1318(6) 0.03077(17) 0.0621(13) Uani 1 1 d . . . H17A H 0.3091 0.1021 0.0079 0.093 Uiso 1 1 calc R . . H17B H 0.4502 0.0888 0.0208 0.093 Uiso 1 1 calc R . . H17C H 0.3875 0.2410 0.0314 0.093 Uiso 1 1 calc R . . C18 C 0.2252(5) 0.6224(6) 0.1432(2) 0.0716(15) Uani 1 1 d . . . H18A H 0.1397 0.6316 0.1315 0.107 Uiso 1 1 calc R . . H18B H 0.2648 0.6194 0.1158 0.107 Uiso 1 1 calc R . . H18C H 0.2541 0.7083 0.1637 0.107 Uiso 1 1 calc R . . Cl1 Cl 0.74168(10) 0.31844(16) 0.00927(4) 0.0584(3) Uani 1 1 d . . . O1 O 0.7967(6) 0.1914(7) -0.0035(3) 0.154(3) Uani 1 1 d . . . O2 O 0.7551(4) 0.4368(7) -0.02442(16) 0.1112(19) Uani 1 1 d . . . O3 O 0.8031(7) 0.3586(7) 0.05569(16) 0.132(2) Uani 1 1 d . . . O4 O 0.6222(4) 0.2929(10) 0.0082(2) 0.146(3) Uani 1 1 d . . . Cl2 Cl 0.45568(10) 0.88854(12) 0.23531(4) 0.0462(2) Uani 1 1 d . . . O5 O 0.4036(5) 0.7574(4) 0.25154(13) 0.0914(15) Uani 1 1 d . . . O6 O 0.5427(5) 0.8491(7) 0.20780(17) 0.1136(19) Uani 1 1 d . . . O7 O 0.5113(3) 0.9744(4) 0.27688(12) 0.0651(9) Uani 1 1 d . . . O8 O 0.3671(3) 0.9781(5) 0.20534(13) 0.0681(9) Uani 1 1 d . . . C1S C 0.9472(7) 0.6851(9) 0.0343(2) 0.095(2) Uiso 1 1 d . . . H1SC H 0.9442 0.7557 0.0081 0.114 Uiso 1 1 d R . . H3SA H 0.8938 0.6070 0.0194 0.114 Uiso 1 1 d R . . H2SB H 1.0296 0.6549 0.0412 0.114 Uiso 1 1 d R . . C2S C 0.9088(5) 0.7738(7) 0.0702(2) 0.0740(15) Uiso 1 1 d . . . N1S N 0.8794(6) 0.8418(8) 0.0993(2) 0.110(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0316(2) 0.0305(2) 0.0324(2) -0.00457(19) 0.00294(17) -0.0023(2) N1 0.0355(16) 0.048(2) 0.0378(16) -0.0071(15) 0.0016(14) -0.0101(16) N2 0.051(2) 0.0370(18) 0.0493(19) -0.0076(16) 0.0039(17) -0.0046(16) N3 0.0359(16) 0.0299(17) 0.0388(16) -0.0022(13) -0.0005(13) -0.0022(13) N4 0.0369(17) 0.046(2) 0.0408(18) -0.0101(15) 0.0039(14) -0.0030(15) N5 0.060(2) 0.049(2) 0.0390(18) 0.0060(16) 0.0049(17) -0.0061(18) C1 0.045(2) 0.052(3) 0.045(2) -0.010(2) 0.0036(18) -0.013(2) C2 0.049(2) 0.039(2) 0.058(3) -0.019(2) -0.001(2) -0.006(2) C3 0.056(3) 0.036(2) 0.061(3) -0.012(2) 0.001(2) 0.010(2) C4 0.049(3) 0.048(2) 0.061(3) -0.010(2) -0.002(2) 0.016(2) C5 0.037(2) 0.053(3) 0.062(3) -0.011(2) -0.002(2) 0.007(2) C6 0.049(2) 0.045(3) 0.041(2) 0.0032(18) -0.0066(18) 0.0017(19) C7 0.061(3) 0.050(3) 0.0321(19) -0.0050(17) 0.0000(19) -0.008(2) C8 0.055(2) 0.055(3) 0.035(2) -0.0019(19) 0.0152(18) -0.007(2) C9 0.040(2) 0.068(3) 0.047(2) -0.014(2) 0.0087(18) 0.008(2) C10 0.0352(18) 0.067(3) 0.038(2) -0.009(2) 0.0053(18) -0.007(2) C11 0.038(2) 0.116(5) 0.059(3) -0.019(3) 0.013(2) -0.014(3) C12 0.042(2) 0.111(5) 0.076(3) -0.030(4) 0.010(2) -0.025(3) C13 0.056(3) 0.071(3) 0.063(3) -0.021(3) 0.005(2) -0.020(3) C14 0.036(2) 0.038(2) 0.058(2) -0.0062(19) 0.0000(19) -0.0081(17) C15 0.058(3) 0.044(2) 0.064(3) -0.001(2) 0.017(2) -0.016(2) C16 0.080(3) 0.042(3) 0.054(3) 0.012(2) 0.010(2) -0.006(2) C17 0.055(3) 0.070(3) 0.060(3) -0.021(3) 0.010(2) -0.009(3) C18 0.061(3) 0.070(3) 0.075(3) -0.017(3) -0.008(3) 0.020(3) Cl1 0.0537(6) 0.0756(8) 0.0473(6) -0.0010(6) 0.0135(5) 0.0006(6) O1 0.123(5) 0.110(5) 0.239(8) -0.079(5) 0.061(5) -0.012(4) O2 0.081(3) 0.167(5) 0.077(3) 0.046(3) -0.005(2) -0.033(3) O3 0.187(6) 0.142(5) 0.055(2) -0.005(3) 0.001(3) -0.012(5) O4 0.062(3) 0.228(7) 0.153(5) 0.093(5) 0.036(3) 0.005(4) Cl2 0.0565(6) 0.0376(5) 0.0464(5) 0.0010(4) 0.0147(5) 0.0049(4) O5 0.154(4) 0.056(2) 0.057(2) 0.0058(18) 0.006(3) -0.035(3) O6 0.142(5) 0.123(4) 0.094(3) 0.005(3) 0.067(3) 0.060(4) O7 0.065(2) 0.068(2) 0.0604(19) -0.0074(17) 0.0097(17) -0.0205(19) O8 0.064(2) 0.072(2) 0.065(2) 0.0180(18) 0.0060(18) 0.0044(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 1.975(3) . ? Cu1 N3 2.032(3) . ? Cu1 N2 2.078(4) . ? Cu1 N4 2.090(3) . ? Cu1 N5 2.163(4) . ? N1 C10 1.336(5) . ? N1 C1 1.340(5) . ? N2 C3 1.451(6) . ? N2 C2 1.506(5) . ? N2 H2B 0.9200 . ? N3 C5 1.491(6) . ? N3 C6 1.507(5) . ? N3 C14 1.508(5) . ? N4 C8 1.490(6) . ? N4 C9 1.504(5) . ? N4 H4C 0.9200 . ? N5 C16 1.468(6) . ? N5 H5A 0.9100 . ? N5 H5B 0.9100 . ? C1 C13 1.381(6) . ? C1 C2 1.494(6) . ? C2 C17 1.528(7) . ? C2 H2A 0.9900 . ? C3 C4 1.509(6) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 C5 1.526(7) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 H5C 0.9800 . ? C5 H5D 0.9800 . ? C6 C7 1.507(6) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.529(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 C18 1.512(8) . ? C9 C10 1.516(6) . ? C9 H9A 0.9900 . ? C10 C11 1.392(6) . ? C11 C12 1.381(8) . ? C11 H11A 0.9400 . ? C12 C13 1.373(8) . ? C12 H12A 0.9400 . ? C13 H13A 0.9400 . ? C14 C15 1.519(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 C16 1.519(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? Cl1 O1 1.373(6) . ? Cl1 O4 1.379(5) . ? Cl1 O3 1.393(5) . ? Cl1 O2 1.440(5) . ? Cl2 O8 1.419(4) . ? Cl2 O6 1.421(4) . ? Cl2 O5 1.422(4) . ? Cl2 O7 1.428(4) . ? C1S C2S 1.415(9) . ? C1S H1SC 0.9603 . ? C1S H3SA 0.9601 . ? C1S H2SB 0.9600 . ? C2S N1S 1.120(8) . ? 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 N3 160.40(14) . . ? N1 Cu1 N2 78.78(14) . . ? N3 Cu1 N2 96.12(13) . . ? N1 Cu1 N4 80.19(13) . . ? N3 Cu1 N4 93.79(13) . . ? N2 Cu1 N4 143.43(15) . . ? N1 Cu1 N5 106.63(15) . . ? N3 Cu1 N5 92.97(14) . . ? N2 Cu1 N5 106.79(15) . . ? N4 Cu1 N5 107.74(16) . . ? C10 N1 C1 122.1(4) . . ? C10 N1 Cu1 118.8(3) . . ? C1 N1 Cu1 118.6(3) . . ? C3 N2 C2 115.7(3) . . ? C3 N2 Cu1 119.2(3) . . ? C2 N2 Cu1 108.5(3) . . ? C3 N2 H2B 103.8 . . ? C2 N2 H2B 103.8 . . ? Cu1 N2 H2B 103.8 . . ? C5 N3 C6 109.0(3) . . ? C5 N3 C14 107.1(3) . . ? C6 N3 C14 108.2(3) . . ? C5 N3 Cu1 113.7(2) . . ? C6 N3 Cu1 106.6(2) . . ? C14 N3 Cu1 112.1(2) . . ? C8 N4 C9 111.7(3) . . ? C8 N4 Cu1 105.1(3) . . ? C9 N4 Cu1 110.4(2) . . ? C8 N4 H4C 109.8 . . ? C9 N4 H4C 109.8 . . ? Cu1 N4 H4C 109.8 . . ? C16 N5 Cu1 113.5(3) . . ? C16 N5 H5A 108.9 . . ? Cu1 N5 H5A 108.9 . . ? C16 N5 H5B 108.9 . . ? Cu1 N5 H5B 108.9 . . ? H5A N5 H5B 107.7 . . ? N1 C1 C13 120.2(4) . . ? N1 C1 C2 114.3(4) . . ? C13 C1 C2 125.5(4) . . ? C1 C2 N2 106.4(3) . . ? C1 C2 C17 109.4(4) . . ? N2 C2 C17 114.0(4) . . ? C1 C2 H2A 108.9 . . ? N2 C2 H2A 108.9 . . ? C17 C2 H2A 108.9 . . ? N2 C3 C4 111.3(4) . . ? N2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? N2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 114.5(4) . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4B 108.6 . . ? C5 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? N3 C5 C4 117.8(4) . . ? N3 C5 H5C 107.9 . . ? C4 C5 H5C 107.9 . . ? N3 C5 H5D 107.9 . . ? C4 C5 H5D 107.9 . . ? H5C C5 H5D 107.2 . . ? N3 C6 C7 117.1(3) . . ? N3 C6 H6A 108.0 . . ? C7 C6 H6A 108.0 . . ? N3 C6 H6B 108.0 . . ? C7 C6 H6B 108.0 . . ? H6A C6 H6B 107.3 . . ? C6 C7 C8 116.7(3) . . ? C6 C7 H7A 108.1 . . ? C8 C7 H7A 108.1 . . ? C6 C7 H7B 108.1 . . ? C8 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? N4 C8 C7 111.6(3) . . ? N4 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N4 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? N4 C9 C18 110.3(4) . . ? N4 C9 C10 107.9(3) . . ? C18 C9 C10 111.5(4) . . ? N4 C9 H9A 109.0 . . ? C18 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N1 C10 C11 120.1(4) . . ? N1 C10 C9 115.6(3) . . ? C11 C10 C9 124.2(4) . . ? C12 C11 C10 117.7(5) . . ? C12 C11 H11A 121.2 . . ? C10 C11 H11A 121.2 . . ? C13 C12 C11 121.5(5) . . ? C13 C12 H12A 119.3 . . ? C11 C12 H12A 119.3 . . ? C12 C13 C1 118.3(5) . . ? C12 C13 H13A 120.9 . . ? C1 C13 H13A 120.9 . . ? N3 C14 C15 116.3(4) . . ? N3 C14 H14A 108.2 . . ? C15 C14 H14A 108.2 . . ? N3 C14 H14B 108.2 . . ? C15 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C14 C15 C16 116.1(4) . . ? C14 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15B 108.3 . . ? C16 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? N5 C16 C15 112.8(4) . . ? N5 C16 H16A 109.0 . . ? C15 C16 H16A 109.0 . . ? N5 C16 H16B 109.0 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C2 C17 H17A 109.5 . . ? C2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C9 C18 H18A 109.5 . . ? C9 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C9 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 Cl1 O4 111.4(5) . . ? O1 Cl1 O3 106.4(5) . . ? O4 Cl1 O3 111.7(4) . . ? O1 Cl1 O2 108.1(5) . . ? O4 Cl1 O2 110.1(3) . . ? O3 Cl1 O2 109.0(3) . . ? O8 Cl2 O6 108.1(3) . . ? O8 Cl2 O5 110.6(3) . . ? O6 Cl2 O5 111.0(3) . . ? O8 Cl2 O7 109.3(2) . . ? O6 Cl2 O7 109.3(3) . . ? O5 Cl2 O7 108.7(2) . . ? C2S C1S H1SC 102.4 . . ? C2S C1S H3SA 116.6 . . ? H1SC C1S H3SA 102.5 . . ? C2S C1S H2SB 116.4 . . ? H1SC C1S H2SB 102.5 . . ? H3SA C1S H2SB 113.4 . . ? N1S C2S C1S 178.5(7) . . ? 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 N3 Cu1 N1 C10 82.1(5) . . . . ? N2 Cu1 N1 C10 158.6(4) . . . . ? N4 Cu1 N1 C10 8.7(3) . . . . ? N5 Cu1 N1 C10 -97.0(4) . . . . ? N3 Cu1 N1 C1 -90.1(5) . . . . ? N2 Cu1 N1 C1 -13.5(3) . . . . ? N4 Cu1 N1 C1 -163.4(3) . . . . ? N5 Cu1 N1 C1 90.8(3) . . . . ? N1 Cu1 N2 C3 164.4(4) . . . . ? N3 Cu1 N2 C3 -34.8(3) . . . . ? N4 Cu1 N2 C3 -139.6(3) . . . . ? N5 Cu1 N2 C3 60.2(4) . . . . ? N1 Cu1 N2 C2 29.0(3) . . . . ? N3 Cu1 N2 C2 -170.2(3) . . . . ? N4 Cu1 N2 C2 85.0(3) . . . . ? N5 Cu1 N2 C2 -75.2(3) . . . . ? N1 Cu1 N3 C5 104.6(5) . . . . ? N2 Cu1 N3 C5 31.0(3) . . . . ? N4 Cu1 N3 C5 175.7(3) . . . . ? N5 Cu1 N3 C5 -76.3(3) . . . . ? N1 Cu1 N3 C6 -15.5(5) . . . . ? N2 Cu1 N3 C6 -89.1(3) . . . . ? N4 Cu1 N3 C6 55.7(3) . . . . ? N5 Cu1 N3 C6 163.7(3) . . . . ? N1 Cu1 N3 C14 -133.8(4) . . . . ? N2 Cu1 N3 C14 152.6(3) . . . . ? N4 Cu1 N3 C14 -62.6(3) . . . . ? N5 Cu1 N3 C14 45.4(3) . . . . ? N1 Cu1 N4 C8 99.6(3) . . . . ? N3 Cu1 N4 C8 -61.6(3) . . . . ? N2 Cu1 N4 C8 44.0(3) . . . . ? N5 Cu1 N4 C8 -155.9(3) . . . . ? N1 Cu1 N4 C9 -21.0(3) . . . . ? N3 Cu1 N4 C9 177.8(3) . . . . ? N2 Cu1 N4 C9 -76.6(4) . . . . ? N5 Cu1 N4 C9 83.5(3) . . . . ? N1 Cu1 N5 C16 132.3(3) . . . . ? N3 Cu1 N5 C16 -47.4(3) . . . . ? N2 Cu1 N5 C16 -144.7(3) . . . . ? N4 Cu1 N5 C16 47.5(4) . . . . ? C10 N1 C1 C13 2.6(7) . . . . ? Cu1 N1 C1 C13 174.5(4) . . . . ? C10 N1 C1 C2 -177.9(4) . . . . ? Cu1 N1 C1 C2 -6.0(5) . . . . ? N1 C1 C2 N2 29.8(5) . . . . ? C13 C1 C2 N2 -150.7(5) . . . . ? N1 C1 C2 C17 -93.9(4) . . . . ? C13 C1 C2 C17 85.6(6) . . . . ? C3 N2 C2 C1 -175.8(4) . . . . ? Cu1 N2 C2 C1 -38.7(4) . . . . ? C3 N2 C2 C17 -55.1(5) . . . . ? Cu1 N2 C2 C17 82.1(4) . . . . ? C2 N2 C3 C4 -174.4(4) . . . . ? Cu1 N2 C3 C4 53.2(5) . . . . ? N2 C3 C4 C5 -67.4(6) . . . . ? C6 N3 C5 C4 67.0(5) . . . . ? C14 N3 C5 C4 -176.1(4) . . . . ? Cu1 N3 C5 C4 -51.7(5) . . . . ? C3 C4 C5 N3 70.1(6) . . . . ? C5 N3 C6 C7 176.5(3) . . . . ? C14 N3 C6 C7 60.4(4) . . . . ? Cu1 N3 C6 C7 -60.5(4) . . . . ? N3 C6 C7 C8 61.6(5) . . . . ? C9 N4 C8 C7 -172.0(4) . . . . ? Cu1 N4 C8 C7 68.3(4) . . . . ? C6 C7 C8 N4 -65.9(5) . . . . ? C8 N4 C9 C18 149.9(4) . . . . ? Cu1 N4 C9 C18 -93.5(4) . . . . ? C8 N4 C9 C10 -88.1(4) . . . . ? Cu1 N4 C9 C10 28.4(4) . . . . ? C1 N1 C10 C11 -3.5(7) . . . . ? Cu1 N1 C10 C11 -175.4(4) . . . . ? C1 N1 C10 C9 177.9(4) . . . . ? Cu1 N1 C10 C9 6.0(5) . . . . ? N4 C9 C10 N1 -23.1(5) . . . . ? C18 C9 C10 N1 98.2(5) . . . . ? N4 C9 C10 C11 158.4(5) . . . . ? C18 C9 C10 C11 -80.3(6) . . . . ? N1 C10 C11 C12 1.5(8) . . . . ? C9 C10 C11 C12 179.9(5) . . . . ? C10 C11 C12 C13 1.5(9) . . . . ? C11 C12 C13 C1 -2.4(9) . . . . ? N1 C1 C13 C12 0.4(8) . . . . ? C2 C1 C13 C12 -179.1(5) . . . . ? C5 N3 C14 C15 65.0(4) . . . . ? C6 N3 C14 C15 -177.7(4) . . . . ? Cu1 N3 C14 C15 -60.4(4) . . . . ? N3 C14 C15 C16 66.7(5) . . . . ? Cu1 N5 C16 C15 58.9(5) . . . . ? C14 C15 C16 N5 -65.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.74 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.595 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.072 #===END data_[Cu(L2b)](ClO4)2 _database_code_CSD 198028 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H42 Cl2 Cu N5 O10' _chemical_formula_weight 695.07 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' Cl Cl 0.1484 0.1585 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.122(2) _cell_length_b 13.595(2) _cell_length_c 14.548(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.128(3) _cell_angle_gamma 90.00 _cell_volume 3063.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 234 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 20.12 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.948 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-3 low-temperature apparatus operating at 213 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 15935 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5392 _reflns_number_gt 3780 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.1336P)^2^+13.4837P] 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 5392 _refine_ls_number_parameters 398 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1310 _refine_ls_R_factor_gt 0.0939 _refine_ls_wR_factor_ref 0.2685 _refine_ls_wR_factor_gt 0.2399 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.001 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 0.32245(5) 0.98497(6) 0.22944(6) 0.0383(3) Uani 1 1 d . . . N1 N 0.2592(4) 0.9119(5) 0.3050(4) 0.0456(15) Uani 1 1 d . . . N2 N 0.2741(5) 1.0991(5) 0.2946(6) 0.063(2) Uani 1 1 d . A . H2A H 0.2167 1.1031 0.2613 0.075 Uiso 1 1 calc R . . N3 N 0.3515(4) 1.0661(5) 0.1261(5) 0.0532(17) Uani 1 1 d . A . N4 N 0.2877(4) 0.8614(5) 0.1434(5) 0.0491(16) Uani 1 1 d . A . H4C H 0.3332 0.8419 0.1211 0.059 Uiso 1 1 calc R . . N5 N 0.4563(4) 0.9723(5) 0.3124(5) 0.0570(18) Uani 1 1 d . A . H5A H 0.4738 1.0308 0.3418 0.068 Uiso 1 1 calc R . . H5B H 0.4604 0.9262 0.3588 0.068 Uiso 1 1 calc R . . C1 C 0.2368(7) 0.9601(8) 0.3732(6) 0.067(3) Uani 1 1 d . A . C2 C 0.2741(11) 1.0624(9) 0.3905(8) 0.112(5) Uani 1 1 d D . . C3 C 0.3067(8) 1.1979(8) 0.2920(9) 0.087(3) Uani 1 1 d . . . H3A H 0.3659 1.2017 0.3340 0.104 Uiso 1 1 calc R A . H3B H 0.2711 1.2440 0.3164 0.104 Uiso 1 1 calc R . . C4 C 0.3062(7) 1.2272(7) 0.1939(9) 0.082(3) Uani 1 1 d . A . H4A H 0.3183 1.2978 0.1936 0.099 Uiso 1 1 calc R . . H4B H 0.2482 1.2163 0.1512 0.099 Uiso 1 1 calc R . . C5 C 0.3700(7) 1.1732(7) 0.1544(9) 0.078(3) Uani 1 1 d . . . H5C H 0.4263 1.1762 0.2023 0.093 Uiso 1 1 calc R A . H5D H 0.3753 1.2091 0.0979 0.093 Uiso 1 1 calc R . . C6 C 0.2734(6) 1.0650(8) 0.0394(6) 0.068(3) Uani 1 1 d . . . H6A H 0.2257 1.0976 0.0568 0.082 Uiso 1 1 calc R A . H6B H 0.2869 1.1044 -0.0110 0.082 Uiso 1 1 calc R . . C7 C 0.2423(6) 0.9653(8) -0.0019(6) 0.065(2) Uani 1 1 d . A . H7A H 0.1934 0.9756 -0.0587 0.077 Uiso 1 1 calc R . . H7B H 0.2887 0.9348 -0.0234 0.077 Uiso 1 1 calc R . . C8 C 0.2147(6) 0.8941(7) 0.0620(6) 0.059(2) Uani 1 1 d . . . H8A H 0.1705 0.9249 0.0872 0.071 Uiso 1 1 calc R A . H8B H 0.1886 0.8364 0.0245 0.071 Uiso 1 1 calc R . . C9 C 0.2621(7) 0.7797(6) 0.1978(7) 0.066(3) Uani 1 1 d . . . H9A H 0.2143 0.7431 0.1535 0.080 Uiso 1 1 calc R A . C10 C 0.2283(5) 0.8231(6) 0.2769(6) 0.0506(19) Uani 1 1 d . A . C11 C 0.1725(6) 0.7755(7) 0.3168(7) 0.065(2) Uani 1 1 d . . . H11A H 0.1509 0.7129 0.2953 0.078 Uiso 1 1 calc R A . C12 C 0.1493(6) 0.8215(10) 0.3885(8) 0.081(3) Uani 1 1 d . A . H12A H 0.1109 0.7902 0.4172 0.097 Uiso 1 1 calc R . . C13 C 0.1817(8) 0.9161(11) 0.4209(8) 0.090(4) Uani 1 1 d . . . H13A H 0.1671 0.9476 0.4717 0.108 Uiso 1 1 calc R A . C14 C 0.4259(6) 1.0249(8) 0.0974(7) 0.074(3) Uani 1 1 d . . . H14A H 0.4207 1.0042 0.0344 0.089 Uiso 1 1 calc R A . C15 C 0.5104(6) 1.0180(9) 0.1749(8) 0.080(3) Uani 1 1 d . A . H15A H 0.5585 1.0563 0.1733 0.096 Uiso 1 1 calc R . . C16 C 0.5136(6) 0.9457(8) 0.2559(8) 0.073(3) Uani 1 1 d . . . H16A H 0.4980 0.8801 0.2287 0.087 Uiso 1 1 calc R A . H16B H 0.5728 0.9425 0.2976 0.087 Uiso 1 1 calc R . . C17 C 0.2471(14) 1.1273(16) 0.4489(15) 0.098(5) Uiso 0.585(16) 1 d PD A 1 H17A H 0.2772 1.1894 0.4507 0.147 Uiso 0.585(16) 1 calc PR A 1 H17B H 0.2598 1.1003 0.5131 0.147 Uiso 0.585(16) 1 calc PR A 1 H17C H 0.1854 1.1379 0.4242 0.147 Uiso 0.585(16) 1 calc PR A 1 C17B C 0.3303(18) 1.070(2) 0.4772(18) 0.098(5) Uiso 0.415(16) 1 d PD A 2 H17D H 0.3527 1.1370 0.4863 0.147 Uiso 0.415(16) 1 calc PR A 2 H17E H 0.3776 1.0247 0.4823 0.147 Uiso 0.415(16) 1 calc PR A 2 H17F H 0.3015 1.0553 0.5257 0.147 Uiso 0.415(16) 1 calc PR A 2 C18 C 0.3321(10) 0.7120(9) 0.2348(11) 0.115(5) Uani 1 1 d . A . H18A H 0.3517 0.6858 0.1824 0.172 Uiso 1 1 calc R . . H18B H 0.3125 0.6584 0.2675 0.172 Uiso 1 1 calc R . . H18C H 0.3794 0.7460 0.2793 0.172 Uiso 1 1 calc R . . Cl1 Cl 0.44942(13) 0.72050(18) 0.01996(15) 0.0574(6) Uani 1 1 d . . . O1 O 0.3657(6) 0.7579(8) -0.0088(7) 0.125(3) Uani 1 1 d . B . O2 O 0.504(2) 0.7937(18) 0.073(2) 0.149(13) Uani 0.50 1 d P B 1 O3 O 0.446(2) 0.6328(18) 0.051(3) 0.131(14) Uani 0.50 1 d P B 1 O4 O 0.4776(16) 0.7180(18) -0.0668(17) 0.091(6) Uani 0.50 1 d P B 1 O2B O 0.503(3) 0.768(5) -0.004(6) 0.38(5) Uani 0.50 1 d P B 2 O3B O 0.4735(13) 0.712(2) 0.1248(10) 0.118(7) Uani 0.50 1 d P B 2 O4B O 0.464(3) 0.620(3) 0.009(3) 0.21(2) Uani 0.50 1 d P B 2 Cl2 Cl 0.03554(14) 0.11034(18) 0.17341(16) 0.0610(6) Uani 1 1 d D . . O5 O 0.0919(10) 0.0315(8) 0.1768(11) 0.193(6) Uiso 1 1 d D C . O6 O 0.034(2) 0.146(2) 0.2640(14) 0.184(11) Uiso 0.50 1 d PDU C 1 O7 O -0.0481(10) 0.0847(17) 0.1195(17) 0.131(7) Uiso 0.50 1 d PDU C 1 O8 O 0.0695(17) 0.1983(14) 0.142(3) 0.233(15) Uiso 0.50 1 d PDU C 1 O6A O 0.0708(11) 0.1985(10) 0.2200(14) 0.110(6) Uiso 0.50 1 d PDU C 2 O7A O -0.0334(16) 0.085(2) 0.213(2) 0.187(11) Uiso 0.50 1 d PDU C 2 O8A O -0.0250(12) 0.1210(16) 0.0827(11) 0.116(6) Uiso 0.50 1 d PDU C 2 O2S O -0.0348(9) 0.3016(7) 0.9346(7) 0.126(4) Uani 1 1 d . . . C1S C 0.0259(8) 0.1677(10) 0.8918(8) 0.092(4) Uani 1 1 d . . . H1SA H -0.0337 0.1540 0.8575 0.137 Uiso 1 1 calc R . . H1SB H 0.0476 0.1160 0.9383 0.137 Uiso 1 1 calc R . . H1SC H 0.0606 0.1704 0.8470 0.137 Uiso 1 1 calc R . . C2S C 0.0309(8) 0.2599(10) 0.9401(7) 0.073(3) Uani 1 1 d . . . C3S C 0.0980(9) 0.2888(12) 0.9826(9) 0.115(5) Uani 1 1 d . . . H3SA H 0.0917 0.3523 1.0103 0.173 Uiso 1 1 calc R . . H3SB H 0.1344 0.2957 0.9399 0.173 Uiso 1 1 calc R . . H3SC H 0.1243 0.2428 1.0332 0.173 Uiso 1 1 calc R . . O1S O 0.1957(8) 0.0788(9) 0.7813(8) 0.142(4) Uani 1 1 d . . . C4S C 0.2140(11) 0.0120(13) 0.6641(11) 0.129(6) Uani 1 1 d . . . H4SA H 0.2725 0.0097 0.7058 0.194 Uiso 1 1 calc R . . H4SB H 0.2127 0.0509 0.6079 0.194 Uiso 1 1 calc R . . H4SC H 0.1943 -0.0542 0.6448 0.194 Uiso 1 1 calc R . . C5S C 0.1700(9) 0.0467(9) 0.7038(8) 0.078(3) Uani 1 1 d . . . C6S C 0.0811(11) 0.0554(12) 0.6569(10) 0.117(5) Uani 1 1 d . . . H6SA H 0.0518 0.0843 0.7003 0.176 Uiso 1 1 calc R . . H6SB H 0.0571 -0.0092 0.6372 0.176 Uiso 1 1 calc R . . H6SC H 0.0732 0.0972 0.6011 0.176 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 0.0379(5) 0.0350(5) 0.0381(5) 0.0005(4) 0.0042(4) -0.0023(4) N1 0.060(4) 0.046(4) 0.031(3) 0.002(3) 0.013(3) 0.001(3) N2 0.068(5) 0.045(4) 0.073(5) -0.010(4) 0.014(4) 0.000(3) N3 0.047(4) 0.048(4) 0.062(4) 0.010(3) 0.011(3) -0.008(3) N4 0.059(4) 0.042(4) 0.047(4) -0.002(3) 0.018(3) -0.005(3) N5 0.045(4) 0.059(4) 0.057(4) 0.003(4) -0.002(3) 0.005(3) C1 0.092(7) 0.075(7) 0.037(4) 0.008(4) 0.024(5) 0.004(5) C2 0.212(16) 0.072(8) 0.049(6) -0.029(6) 0.033(8) -0.006(9) C3 0.093(8) 0.053(6) 0.096(8) -0.021(6) -0.003(6) 0.007(5) C4 0.080(7) 0.031(5) 0.128(10) 0.002(5) 0.015(7) -0.006(4) C5 0.066(6) 0.054(6) 0.106(8) 0.014(6) 0.015(6) -0.014(5) C6 0.072(6) 0.073(7) 0.051(5) 0.026(5) 0.005(5) 0.000(5) C7 0.064(6) 0.087(7) 0.038(4) 0.007(4) 0.006(4) -0.001(5) C8 0.055(5) 0.064(6) 0.051(5) -0.016(4) 0.002(4) -0.018(4) C9 0.102(8) 0.039(5) 0.064(6) 0.000(4) 0.033(5) -0.011(5) C10 0.054(5) 0.048(5) 0.050(5) 0.007(4) 0.014(4) -0.005(4) C11 0.060(6) 0.066(6) 0.069(6) 0.023(5) 0.020(5) -0.004(4) C12 0.057(6) 0.110(10) 0.081(7) 0.049(7) 0.028(5) 0.014(6) C13 0.104(9) 0.123(11) 0.057(6) 0.010(7) 0.046(6) 0.026(8) C14 0.063(6) 0.101(8) 0.064(6) 0.022(6) 0.027(5) 0.000(5) C15 0.041(5) 0.103(8) 0.096(8) 0.015(7) 0.021(5) -0.005(5) C16 0.041(5) 0.087(7) 0.082(7) -0.003(6) 0.003(5) 0.006(5) C18 0.152(13) 0.077(8) 0.134(12) 0.033(8) 0.069(10) 0.045(8) Cl1 0.0488(12) 0.0649(15) 0.0534(12) -0.0071(10) 0.0059(9) 0.0114(10) O1 0.081(6) 0.184(10) 0.102(6) 0.015(6) 0.015(5) 0.054(6) O2 0.17(3) 0.089(16) 0.13(2) -0.050(17) -0.055(18) 0.003(15) O3 0.15(2) 0.072(16) 0.21(4) 0.06(2) 0.11(3) 0.051(15) O4 0.096(13) 0.095(13) 0.103(13) -0.025(12) 0.061(11) -0.010(10) O2B 0.19(5) 0.42(9) 0.61(12) 0.38(8) 0.24(8) 0.06(5) O3B 0.132(16) 0.16(2) 0.043(9) -0.017(11) -0.011(9) 0.032(15) O4B 0.26(5) 0.15(3) 0.16(3) -0.06(2) -0.03(3) 0.13(3) Cl2 0.0492(12) 0.0698(15) 0.0602(13) 0.0026(11) 0.0087(10) 0.0089(10) O2S 0.195(11) 0.106(7) 0.088(6) 0.009(5) 0.057(7) 0.036(7) C1S 0.083(8) 0.116(10) 0.071(7) 0.000(7) 0.013(6) 0.015(7) C2S 0.076(7) 0.097(9) 0.049(6) -0.003(6) 0.024(5) -0.001(6) C3S 0.107(11) 0.147(13) 0.082(9) -0.042(9) 0.009(8) -0.044(9) O1S 0.186(11) 0.142(10) 0.092(7) 0.026(7) 0.030(7) -0.042(8) C4S 0.110(12) 0.180(17) 0.100(11) -0.002(11) 0.033(10) 0.032(11) C5S 0.108(10) 0.084(8) 0.047(6) 0.014(5) 0.028(7) 0.000(7) C6S 0.142(14) 0.120(12) 0.090(9) 0.007(9) 0.032(10) -0.002(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 Cu1 N1 1.964(6) . ? Cu1 N3 2.022(7) . ? Cu1 N4 2.077(6) . ? Cu1 N2 2.080(7) . ? Cu1 N5 2.167(7) . ? N1 C1 1.320(11) . ? N1 C10 1.328(10) . ? N2 C3 1.447(13) . ? N2 C2 1.482(14) . ? N3 C14 1.484(12) . ? N3 C6 1.514(11) . ? N3 C5 1.520(12) . ? N4 C8 1.486(11) . ? N4 C9 1.488(10) . ? N5 C16 1.443(12) . ? C1 C13 1.404(15) . ? C1 C2 1.508(16) . ? C2 C17B 1.34(2) . ? C2 C17 1.378(19) . ? C3 C4 1.480(16) . ? C4 C5 1.501(15) . ? C6 C7 1.510(14) . ? C7 C8 1.494(12) . ? C9 C18 1.441(15) . ? C9 C10 1.522(12) . ? C10 C11 1.360(12) . ? C11 C12 1.356(15) . ? C12 C13 1.418(17) . ? C14 C15 1.511(14) . ? C15 C16 1.523(15) . ? Cl1 O2B 1.21(3) . ? Cl1 O3 1.28(2) . ? Cl1 O1 1.394(8) . ? Cl1 O4B 1.40(3) . ? Cl1 O2 1.40(2) . ? Cl1 O4 1.46(2) . ? Cl1 O3B 1.471(15) . ? Cl2 O5 1.398(10) . ? Cl2 O7 1.402(12) . ? Cl2 O6 1.413(13) . ? Cl2 O8A 1.415(13) . ? Cl2 O6A 1.416(12) . ? Cl2 O7A 1.427(15) . ? Cl2 O8 1.442(13) . ? O2S C2S 1.184(14) . ? C1S C2S 1.429(16) . ? C2S C3S 1.156(15) . ? O1S C5S 1.172(14) . ? C4S C5S 1.133(17) . ? C5S C6S 1.411(18) . ? 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 N3 162.9(3) . . ? N1 Cu1 N4 80.4(3) . . ? N3 Cu1 N4 94.1(3) . . ? N1 Cu1 N2 78.7(3) . . ? N3 Cu1 N2 97.2(3) . . ? N4 Cu1 N2 143.7(3) . . ? N1 Cu1 N5 103.9(3) . . ? N3 Cu1 N5 93.3(3) . . ? N4 Cu1 N5 109.4(3) . . ? N2 Cu1 N5 104.3(3) . . ? C1 N1 C10 121.7(8) . . ? C1 N1 Cu1 117.6(6) . . ? C10 N1 Cu1 119.8(5) . . ? C3 N2 C2 115.6(8) . . ? C3 N2 Cu1 119.7(7) . . ? C2 N2 Cu1 106.0(6) . . ? C14 N3 C6 108.2(8) . . ? C14 N3 C5 109.0(7) . . ? C6 N3 C5 106.9(7) . . ? C14 N3 Cu1 112.0(5) . . ? C6 N3 Cu1 107.6(5) . . ? C5 N3 Cu1 112.9(6) . . ? C8 N4 C9 111.8(7) . . ? C8 N4 Cu1 105.1(5) . . ? C9 N4 Cu1 110.6(5) . . ? C16 N5 Cu1 113.5(6) . . ? N1 C1 C13 120.2(10) . . ? N1 C1 C2 113.8(9) . . ? C13 C1 C2 126.1(10) . . ? C17B C2 C17 67.2(16) . . ? C17B C2 N2 133.1(19) . . ? C17 C2 N2 116.6(13) . . ? C17B C2 C1 111.5(17) . . ? C17 C2 C1 120.9(15) . . ? N2 C2 C1 105.0(7) . . ? N2 C3 C4 111.7(8) . . ? C3 C4 C5 114.6(9) . . ? C4 C5 N3 118.0(8) . . ? C7 C6 N3 116.6(7) . . ? C8 C7 C6 117.2(7) . . ? N4 C8 C7 112.5(7) . . ? C18 C9 N4 111.8(9) . . ? C18 C9 C10 111.9(9) . . ? N4 C9 C10 108.9(7) . . ? N1 C10 C11 122.5(8) . . ? N1 C10 C9 113.7(7) . . ? C11 C10 C9 123.8(8) . . ? C12 C11 C10 117.7(10) . . ? C11 C12 C13 121.2(9) . . ? C1 C13 C12 116.6(10) . . ? N3 C14 C15 116.4(9) . . ? C14 C15 C16 116.5(8) . . ? N5 C16 C15 112.9(8) . . ? O2B Cl1 O3 135(3) . . ? O2B Cl1 O1 115(2) . . ? O3 Cl1 O1 108.5(14) . . ? O2B Cl1 O4B 109(4) . . ? O3 Cl1 O4B 33(2) . . ? O1 Cl1 O4B 120(2) . . ? O2B Cl1 O2 53(4) . . ? O3 Cl1 O2 123(2) . . ? O1 Cl1 O2 108.0(13) . . ? O4B Cl1 O2 131(2) . . ? O2B Cl1 O4 49(5) . . ? O3 Cl1 O4 109.7(16) . . ? O1 Cl1 O4 104.9(12) . . ? O4B Cl1 O4 77(2) . . ? O2 Cl1 O4 101.2(19) . . ? O2B Cl1 O3B 110(4) . . ? O3 Cl1 O3B 65.3(19) . . ? O1 Cl1 O3B 107.2(9) . . ? O4B Cl1 O3B 91.9(18) . . ? O2 Cl1 O3B 62.9(14) . . ? O4 Cl1 O3B 147.3(13) . . ? O5 Cl2 O7 110.1(12) . . ? O5 Cl2 O6 114.5(12) . . ? O7 Cl2 O6 110.0(16) . . ? O5 Cl2 O8A 112.6(11) . . ? O7 Cl2 O8A 36.5(11) . . ? O6 Cl2 O8A 130.3(14) . . ? O5 Cl2 O6A 117.5(9) . . ? O7 Cl2 O6A 132.4(12) . . ? O6 Cl2 O6A 51.0(14) . . ? O8A Cl2 O6A 116.2(12) . . ? O5 Cl2 O7A 111.8(14) . . ? O7 Cl2 O7A 55.2(13) . . ? O6 Cl2 O7A 59.3(16) . . ? O8A Cl2 O7A 89.2(15) . . ? O6A Cl2 O7A 105.5(15) . . ? O5 Cl2 O8 110.2(12) . . ? O7 Cl2 O8 114.7(13) . . ? O6 Cl2 O8 96.8(19) . . ? O8A Cl2 O8 80.9(15) . . ? O6A Cl2 O8 46.7(14) . . ? O7A Cl2 O8 137.4(18) . . ? C3S C2S O2S 124.1(15) . . ? C3S C2S C1S 118.5(14) . . ? O2S C2S C1S 117.4(12) . . ? C4S C5S O1S 122.7(17) . . ? C4S C5S C6S 119.0(14) . . ? O1S C5S C6S 118.3(14) . . ? 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 N3 Cu1 N1 C1 -93.2(11) . . . . ? N4 Cu1 N1 C1 -165.8(7) . . . . ? N2 Cu1 N1 C1 -15.6(7) . . . . ? N5 Cu1 N1 C1 86.5(7) . . . . ? N3 Cu1 N1 C10 75.9(12) . . . . ? N4 Cu1 N1 C10 3.3(6) . . . . ? N2 Cu1 N1 C10 153.4(7) . . . . ? N5 Cu1 N1 C10 -104.5(6) . . . . ? N1 Cu1 N2 C3 167.2(8) . . . . ? N3 Cu1 N2 C3 -29.6(8) . . . . ? N4 Cu1 N2 C3 -136.8(7) . . . . ? N5 Cu1 N2 C3 65.6(8) . . . . ? N1 Cu1 N2 C2 34.3(8) . . . . ? N3 Cu1 N2 C2 -162.6(8) . . . . ? N4 Cu1 N2 C2 90.2(9) . . . . ? N5 Cu1 N2 C2 -67.4(8) . . . . ? N1 Cu1 N3 C14 -135.1(9) . . . . ? N4 Cu1 N3 C14 -64.5(6) . . . . ? N2 Cu1 N3 C14 150.1(6) . . . . ? N5 Cu1 N3 C14 45.2(7) . . . . ? N1 Cu1 N3 C6 -16.3(13) . . . . ? N4 Cu1 N3 C6 54.3(6) . . . . ? N2 Cu1 N3 C6 -91.1(6) . . . . ? N5 Cu1 N3 C6 164.0(6) . . . . ? N1 Cu1 N3 C5 101.4(10) . . . . ? N4 Cu1 N3 C5 172.0(6) . . . . ? N2 Cu1 N3 C5 26.5(6) . . . . ? N5 Cu1 N3 C5 -78.3(6) . . . . ? N1 Cu1 N4 C8 103.4(5) . . . . ? N3 Cu1 N4 C8 -60.3(5) . . . . ? N2 Cu1 N4 C8 47.9(7) . . . . ? N5 Cu1 N4 C8 -155.2(5) . . . . ? N1 Cu1 N4 C9 -17.4(6) . . . . ? N3 Cu1 N4 C9 179.0(6) . . . . ? N2 Cu1 N4 C9 -72.9(8) . . . . ? N5 Cu1 N4 C9 84.1(6) . . . . ? N1 Cu1 N5 C16 133.3(7) . . . . ? N3 Cu1 N5 C16 -46.8(7) . . . . ? N4 Cu1 N5 C16 48.7(7) . . . . ? N2 Cu1 N5 C16 -145.1(7) . . . . ? C10 N1 C1 C13 2.6(14) . . . . ? Cu1 N1 C1 C13 171.4(8) . . . . ? C10 N1 C1 C2 -176.2(9) . . . . ? Cu1 N1 C1 C2 -7.4(11) . . . . ? C3 N2 C2 C17B -40(3) . . . . ? Cu1 N2 C2 C17B 95(2) . . . . ? C3 N2 C2 C17 42.6(19) . . . . ? Cu1 N2 C2 C17 177.8(14) . . . . ? C3 N2 C2 C1 179.4(9) . . . . ? Cu1 N2 C2 C1 -45.4(11) . . . . ? N1 C1 C2 C17B -114.0(18) . . . . ? C13 C1 C2 C17B 67(2) . . . . ? N1 C1 C2 C17 170.4(14) . . . . ? C13 C1 C2 C17 -8(2) . . . . ? N1 C1 C2 N2 35.9(14) . . . . ? C13 C1 C2 N2 -142.8(11) . . . . ? C2 N2 C3 C4 178.6(10) . . . . ? Cu1 N2 C3 C4 49.8(11) . . . . ? N2 C3 C4 C5 -68.8(12) . . . . ? C3 C4 C5 N3 72.4(13) . . . . ? C14 N3 C5 C4 -175.0(9) . . . . ? C6 N3 C5 C4 68.3(11) . . . . ? Cu1 N3 C5 C4 -49.8(11) . . . . ? C14 N3 C6 C7 63.0(10) . . . . ? C5 N3 C6 C7 -179.7(8) . . . . ? Cu1 N3 C6 C7 -58.2(9) . . . . ? N3 C6 C7 C8 60.3(12) . . . . ? C9 N4 C8 C7 -171.5(7) . . . . ? Cu1 N4 C8 C7 68.6(8) . . . . ? C6 C7 C8 N4 -66.6(11) . . . . ? C8 N4 C9 C18 146.1(10) . . . . ? Cu1 N4 C9 C18 -97.2(9) . . . . ? C8 N4 C9 C10 -89.7(8) . . . . ? Cu1 N4 C9 C10 26.9(9) . . . . ? C1 N1 C10 C11 -0.6(13) . . . . ? Cu1 N1 C10 C11 -169.2(7) . . . . ? C1 N1 C10 C9 -179.8(8) . . . . ? Cu1 N1 C10 C9 11.6(10) . . . . ? C18 C9 C10 N1 98.7(10) . . . . ? N4 C9 C10 N1 -25.4(11) . . . . ? C18 C9 C10 C11 -80.5(13) . . . . ? N4 C9 C10 C11 155.5(8) . . . . ? N1 C10 C11 C12 -0.8(13) . . . . ? C9 C10 C11 C12 178.3(9) . . . . ? C10 C11 C12 C13 0.1(15) . . . . ? N1 C1 C13 C12 -3.1(15) . . . . ? C2 C1 C13 C12 175.6(11) . . . . ? C11 C12 C13 C1 1.8(16) . . . . ? C6 N3 C14 C15 -179.0(8) . . . . ? C5 N3 C14 C15 65.2(10) . . . . ? Cu1 N3 C14 C15 -60.5(10) . . . . ? N3 C14 C15 C16 66.8(13) . . . . ? Cu1 N5 C16 C15 57.7(10) . . . . ? C14 C15 C16 N5 -64.8(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.607 _refine_diff_density_min -0.806 _refine_diff_density_rms 0.120 #===END data_[Cu(L3c)](ClO4)2 _database_code_CSD 198029 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H31 Cl2 Cu N5 O9' _chemical_formula_weight 595.92 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' Cl Cl 0.1484 0.1585 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.2060(17) _cell_length_b 19.104(3) _cell_length_c 13.750(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.698(3) _cell_angle_gamma 90.00 _cell_volume 2615.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description chunk _exptl_crystal_colour purple _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type 'Semi-empirical, SADABS' _exptl_absorpt_correction_T_min 0.8274 _exptl_absorpt_correction_T_max 0.8985 _exptl_absorpt_process_details ? _exptl_special_details ; Data was collected using a BRUKER SMART CCD (charge coupled devi ce) based diffractometer equipped with an Oxford Cryostream low-temperature apparatus oper 193 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3\% per frame for 30 s , such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.75 \%A. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, incorporated in SHELXTL V5.1. Carbon-bound H atoms were placed in idealized positions and refined as a riding model. ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w, 0.3 deg' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 19047 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0884 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.37 _reflns_number_total 6539 _reflns_number_gt 3661 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ASTRO (BRUKER, V5.007, 1997)' _computing_cell_refinement 'SMART (BRUKER, V5.054, 1998)' _computing_data_reduction 'SAINT (BRUKER, V6.01, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (BRUKER, 1998, V5.1)' _computing_publication_material 'XCIF (Sheldrick and BRUKER, 1997, V5.1)' _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^)+(0.1716P)^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 6539 _refine_ls_number_parameters 309 _refine_ls_number_restraints 23 _refine_ls_R_factor_all 0.1320 _refine_ls_R_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.2752 _refine_ls_wR_factor_gt 0.2514 _refine_ls_goodness_of_fit_ref 0.993 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.19057(7) 0.19451(4) 0.70397(5) 0.0331(3) Uani 1 1 d . . . O1 O -0.1742(9) -0.1459(4) 0.4751(4) 0.098(3) Uani 1 1 d . . . N1 N 0.2581(5) 0.2763(3) 0.6478(4) 0.0348(11) Uani 1 1 d . . . N2 N 0.0105(5) 0.2390(2) 0.6446(3) 0.0312(11) Uani 1 1 d . . . H2C H -0.0247 0.2140 0.5866 0.037 Uiso 1 1 calc R . . N3 N 0.1187(5) 0.1096(3) 0.7612(4) 0.0339(11) Uani 1 1 d . . . N4 N 0.3831(5) 0.1634(3) 0.7219(5) 0.0455(14) Uani 1 1 d . . . H4C H 0.3826 0.1356 0.6663 0.055 Uiso 1 1 calc R . . N5 N -0.1478(7) -0.0999(3) 0.6272(4) 0.0548(17) Uani 1 1 d . . . H5C H -0.1661 -0.1035 0.6867 0.066 Uiso 1 1 calc R . . C1 C 0.1710(7) 0.3238(3) 0.6016(4) 0.0329(13) Uani 1 1 d . . . C2 C 0.0293(7) 0.3117(3) 0.6124(5) 0.0391(14) Uani 1 1 d . . . H2A H 0.0079 0.3449 0.6620 0.047 Uiso 1 1 calc R . . H2B H -0.0335 0.3208 0.5478 0.047 Uiso 1 1 calc R . . C3 C -0.0925(7) 0.2364(3) 0.7046(5) 0.0432(16) Uani 1 1 d . . . H3A H -0.1782 0.2546 0.6643 0.052 Uiso 1 1 calc R . . H3B H -0.0648 0.2672 0.7634 0.052 Uiso 1 1 calc R . . C4 C -0.1147(7) 0.1630(3) 0.7396(5) 0.0412(15) Uani 1 1 d . . . H4A H -0.1906 0.1640 0.7737 0.049 Uiso 1 1 calc R . . H4B H -0.1410 0.1323 0.6805 0.049 Uiso 1 1 calc R . . C5 C 0.0058(7) 0.1313(3) 0.8094(5) 0.0391(14) Uani 1 1 d . . . H5A H 0.0412 0.1656 0.8626 0.047 Uiso 1 1 calc R . . H5B H -0.0241 0.0896 0.8416 0.047 Uiso 1 1 calc R . . C6 C 0.2234(7) 0.0771(4) 0.8429(5) 0.0460(17) Uani 1 1 d . . . H6A H 0.1845 0.0346 0.8665 0.055 Uiso 1 1 calc R . . H6B H 0.2436 0.1103 0.8995 0.055 Uiso 1 1 calc R . . C7 C 0.3542(8) 0.0571(4) 0.8157(6) 0.055(2) Uani 1 1 d . . . H7A H 0.4043 0.0253 0.8676 0.066 Uiso 1 1 calc R . . H7B H 0.3339 0.0311 0.7519 0.066 Uiso 1 1 calc R . . C8 C 0.4422(8) 0.1186(4) 0.8055(6) 0.0540(19) Uani 1 1 d . . . H8A H 0.4582 0.1464 0.8677 0.065 Uiso 1 1 calc R . . H8B H 0.5302 0.1012 0.7965 0.065 Uiso 1 1 calc R . . C9 C 0.4700(7) 0.2236(4) 0.7088(7) 0.062(2) Uani 1 1 d . . . H9A H 0.5404 0.2076 0.6747 0.075 Uiso 1 1 calc R . . H9B H 0.5148 0.2422 0.7750 0.075 Uiso 1 1 calc R . . C10 C 0.3896(7) 0.2803(4) 0.6493(5) 0.0419(15) Uani 1 1 d . . . C11 C 0.4397(8) 0.3337(4) 0.6039(5) 0.0486(17) Uani 1 1 d . . . H11 H 0.5331 0.3367 0.6054 0.058 Uiso 1 1 calc R . . C12 C 0.3490(8) 0.3847(3) 0.5542(5) 0.0444(16) Uani 1 1 d . . . H12 H 0.3810 0.4228 0.5216 0.053 Uiso 1 1 calc R . . C13 C 0.2158(7) 0.3792(3) 0.5531(4) 0.0373(14) Uani 1 1 d . . . H13 H 0.1542 0.4131 0.5193 0.045 Uiso 1 1 calc R . . C14 C 0.0718(7) 0.0598(3) 0.6764(4) 0.0359(14) Uani 1 1 d . . . H14A H 0.1508 0.0453 0.6504 0.043 Uiso 1 1 calc R . . H14B H 0.0104 0.0854 0.6223 0.043 Uiso 1 1 calc R . . C15 C 0.0002(8) -0.0060(3) 0.7002(5) 0.0442(16) Uani 1 1 d . . . H15A H 0.0664 -0.0385 0.7402 0.053 Uiso 1 1 calc R . . H15B H -0.0660 0.0067 0.7401 0.053 Uiso 1 1 calc R . . C16 C -0.0691(10) -0.0410(4) 0.6073(5) 0.056(2) Uani 1 1 d . . . H16A H -0.1287 -0.0070 0.5646 0.068 Uiso 1 1 calc R . . H16B H -0.0017 -0.0574 0.5705 0.068 Uiso 1 1 calc R . . C17 C -0.1936(8) -0.1488(4) 0.5602(5) 0.0514(18) Uani 1 1 d . . . C18 C -0.2740(9) -0.2065(4) 0.5906(6) 0.059(2) Uani 1 1 d . . . H18A H -0.3695 -0.1987 0.5616 0.089 Uiso 1 1 calc R . . H18B H -0.2595 -0.2077 0.6634 0.089 Uiso 1 1 calc R . . H18C H -0.2461 -0.2513 0.5667 0.089 Uiso 1 1 calc R . . Cl1 Cl 0.76568(16) 0.45983(8) 0.63202(12) 0.0373(4) Uani 1 1 d . . . O2 O 0.8673(5) 0.4611(2) 0.5750(4) 0.0476(12) Uani 1 1 d . . . O3 O 0.7715(6) 0.3976(3) 0.6889(4) 0.0588(14) Uani 1 1 d . . . O4 O 0.6358(5) 0.4642(3) 0.5673(4) 0.0650(16) Uani 1 1 d . . . O5 O 0.7810(7) 0.5188(3) 0.6975(5) 0.081(2) Uani 1 1 d . . . Cl2 Cl 0.2458(5) 0.31385(15) 0.9144(2) 0.145(2) Uani 1 1 d D . . O6 O 0.2693(12) 0.2504(5) 0.8791(8) 0.055(3) Uiso 0.50 1 d PD A 1 O8 O 0.160(2) 0.2904(13) 0.9846(17) 0.152(8) Uiso 0.50 1 d PD A 1 O9 O 0.1753(17) 0.3564(8) 0.8409(11) 0.216(6) Uiso 1 1 d D A 1 O10 O 0.3296(11) 0.3478(5) 0.9827(7) 0.046(2) Uiso 0.50 1 d PD A 1 O6B O 0.1829(15) 0.2621(7) 0.8562(11) 0.094(5) Uiso 0.50 1 d PD A 2 O8B O 0.270(2) 0.3469(10) 1.0034(12) 0.126(7) Uiso 0.50 1 d PD A 2 O10B O 0.3863(14) 0.2946(12) 0.9035(16) 0.150(8) Uiso 0.50 1 d PD A 2 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 0.0286(4) 0.0316(4) 0.0366(4) 0.0116(3) 0.0021(3) -0.0008(3) O1 0.159(7) 0.110(5) 0.036(3) -0.022(3) 0.042(4) -0.091(5) N1 0.036(3) 0.033(3) 0.034(3) 0.005(2) 0.004(2) -0.004(2) N2 0.035(3) 0.030(2) 0.029(2) 0.0050(19) 0.007(2) 0.005(2) N3 0.039(3) 0.032(3) 0.029(2) 0.008(2) 0.005(2) -0.002(2) N4 0.029(3) 0.050(3) 0.052(3) 0.017(3) 0.000(2) 0.005(3) N5 0.089(5) 0.051(3) 0.031(3) -0.007(2) 0.028(3) -0.029(3) C1 0.040(3) 0.029(3) 0.028(3) -0.003(2) 0.004(3) -0.001(2) C2 0.044(4) 0.032(3) 0.040(3) 0.008(3) 0.007(3) 0.005(3) C3 0.046(4) 0.040(4) 0.047(4) 0.003(3) 0.019(3) 0.005(3) C4 0.039(4) 0.040(3) 0.049(4) -0.003(3) 0.020(3) -0.005(3) C5 0.048(4) 0.037(3) 0.035(3) 0.001(3) 0.015(3) -0.007(3) C6 0.051(4) 0.044(4) 0.039(3) 0.014(3) 0.003(3) 0.001(3) C7 0.051(4) 0.048(4) 0.061(5) 0.021(3) 0.001(4) 0.013(4) C8 0.042(4) 0.059(5) 0.057(4) 0.018(4) 0.002(3) 0.011(3) C9 0.026(4) 0.070(5) 0.086(6) 0.030(5) 0.001(4) -0.003(3) C10 0.032(3) 0.046(4) 0.045(4) 0.008(3) 0.003(3) -0.006(3) C11 0.042(4) 0.051(4) 0.054(4) 0.001(3) 0.012(3) -0.017(3) C12 0.062(5) 0.033(3) 0.037(3) 0.000(3) 0.010(3) -0.015(3) C13 0.052(4) 0.026(3) 0.033(3) 0.002(2) 0.006(3) -0.003(3) C14 0.044(4) 0.038(3) 0.028(3) 0.004(2) 0.013(3) 0.000(3) C15 0.064(5) 0.037(3) 0.032(3) 0.007(3) 0.011(3) -0.006(3) C16 0.088(6) 0.047(4) 0.040(4) 0.002(3) 0.026(4) -0.022(4) C17 0.067(5) 0.056(4) 0.035(3) -0.005(3) 0.018(3) -0.019(4) C18 0.071(6) 0.066(5) 0.048(4) -0.007(4) 0.027(4) -0.021(4) Cl1 0.0360(8) 0.0340(7) 0.0438(8) 0.0035(6) 0.0129(7) 0.0001(6) O2 0.043(3) 0.049(3) 0.054(3) 0.007(2) 0.020(2) 0.002(2) O3 0.070(4) 0.058(3) 0.056(3) 0.024(3) 0.032(3) 0.017(3) O4 0.040(3) 0.076(4) 0.074(4) 0.027(3) 0.002(3) -0.006(3) O5 0.076(4) 0.061(4) 0.116(5) -0.044(4) 0.042(4) -0.020(3) Cl2 0.225(5) 0.0670(17) 0.085(2) -0.0177(14) -0.090(3) 0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.936(5) . ? Cu1 N3 2.010(5) . ? Cu1 N4 2.015(6) . ? Cu1 N2 2.027(5) . ? O1 C17 1.230(8) . ? N1 C1 1.329(8) . ? N1 C10 1.340(8) . ? N2 C3 1.472(8) . ? N2 C2 1.483(7) . ? N2 H2C 0.9300 . ? N3 C14 1.500(8) . ? N3 C6 1.504(8) . ? N3 C5 1.508(8) . ? N4 C8 1.454(9) . ? N4 C9 1.487(9) . ? N4 H4C 0.9300 . ? N5 C17 1.322(9) . ? N5 C16 1.442(9) . ? N5 H5C 0.8800 . ? C1 C13 1.382(8) . ? C1 C2 1.504(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.516(9) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.511(10) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.512(11) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.504(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.489(10) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.354(9) . ? C11 C12 1.413(10) . ? C11 H11 0.9500 . ? C12 C13 1.361(10) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.526(9) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.478(10) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.489(10) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? Cl1 O3 1.417(5) . ? Cl1 O4 1.427(6) . ? Cl1 O5 1.429(6) . ? Cl1 O2 1.431(5) . ? Cl2 O10 1.296(9) . ? Cl2 O6B 1.343(11) . ? Cl2 O6 1.347(9) . ? Cl2 O8B 1.351(12) . ? Cl2 O9 1.371(12) . ? Cl2 O8 1.507(14) . ? Cl2 O10B 1.519(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 N1 Cu1 N3 179.4(2) . . ? N1 Cu1 N4 82.2(2) . . ? N3 Cu1 N4 98.3(2) . . ? N1 Cu1 N2 82.6(2) . . ? N3 Cu1 N2 96.8(2) . . ? N4 Cu1 N2 161.2(2) . . ? C1 N1 C10 122.1(6) . . ? C1 N1 Cu1 118.8(4) . . ? C10 N1 Cu1 118.8(4) . . ? C3 N2 C2 110.7(5) . . ? C3 N2 Cu1 117.1(4) . . ? C2 N2 Cu1 110.3(4) . . ? C3 N2 H2C 106.0 . . ? C2 N2 H2C 106.0 . . ? Cu1 N2 H2C 106.0 . . ? C14 N3 C6 111.8(5) . . ? C14 N3 C5 111.9(5) . . ? C6 N3 C5 105.7(5) . . ? C14 N3 Cu1 106.8(3) . . ? C6 N3 Cu1 111.4(4) . . ? C5 N3 Cu1 109.3(4) . . ? C8 N4 C9 113.4(6) . . ? C8 N4 Cu1 119.6(5) . . ? C9 N4 Cu1 110.4(4) . . ? C8 N4 H4C 103.8 . . ? C9 N4 H4C 103.8 . . ? Cu1 N4 H4C 103.8 . . ? C17 N5 C16 123.0(6) . . ? C17 N5 H5C 118.5 . . ? C16 N5 H5C 118.5 . . ? N1 C1 C13 119.8(6) . . ? N1 C1 C2 113.9(5) . . ? C13 C1 C2 126.3(6) . . ? N2 C2 C1 111.3(5) . . ? N2 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? N2 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N2 C3 C4 112.6(5) . . ? N2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? N2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 114.5(6) . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? N3 C5 C4 115.1(5) . . ? N3 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? N3 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? N3 C6 C7 116.1(6) . . ? N3 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? N3 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C8 C7 C6 113.8(6) . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N4 C8 C7 112.4(6) . . ? N4 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? N4 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? N4 C9 C10 110.9(6) . . ? N4 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? N4 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? N1 C10 C11 120.9(6) . . ? N1 C10 C9 113.4(6) . . ? C11 C10 C9 125.6(7) . . ? C10 C11 C12 118.0(7) . . ? C10 C11 H11 121.0 . . ? C12 C11 H11 121.0 . . ? C13 C12 C11 120.0(6) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C1 119.3(6) . . ? C12 C13 H13 120.4 . . ? C1 C13 H13 120.4 . . ? N3 C14 C15 116.2(5) . . ? N3 C14 H14A 108.2 . . ? C15 C14 H14A 108.2 . . ? N3 C14 H14B 108.2 . . ? C15 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C14 110.4(5) . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N5 C16 C15 111.7(5) . . ? N5 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? N5 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? O1 C17 N5 121.7(7) . . ? O1 C17 C18 120.9(7) . . ? N5 C17 C18 117.4(6) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 Cl1 O4 108.3(3) . . ? O3 Cl1 O5 109.1(4) . . ? O4 Cl1 O5 107.7(4) . . ? O3 Cl1 O2 111.7(3) . . ? O4 Cl1 O2 110.1(3) . . ? O5 Cl1 O2 109.9(3) . . ? O10 Cl2 O6B 162.3(9) . . ? O10 Cl2 O6 124.8(8) . . ? O6B Cl2 O6 39.0(7) . . ? O10 Cl2 O8B 31.6(9) . . ? O6B Cl2 O8B 148.6(12) . . ? O6 Cl2 O8B 137.4(10) . . ? O10 Cl2 O9 113.2(9) . . ? O6B Cl2 O9 83.7(10) . . ? O6 Cl2 O9 111.9(9) . . ? O8B Cl2 O9 110.7(12) . . ? O10 Cl2 O8 93.9(11) . . ? O6B Cl2 O8 83.9(12) . . ? O6 Cl2 O8 97.9(11) . . ? O8B Cl2 O8 65.0(13) . . ? O9 Cl2 O8 111.3(14) . . ? O10 Cl2 O10B 72.9(9) . . ? O6B Cl2 O10B 95.8(9) . . ? O6 Cl2 O10B 60.0(9) . . ? O8B Cl2 O10B 102.2(10) . . ? O9 Cl2 O10B 115.2(13) . . ? O8 Cl2 O10B 133.3(14) . . ? 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 N3 Cu1 N1 C1 26(23) . . . . ? N4 Cu1 N1 C1 170.7(5) . . . . ? N2 Cu1 N1 C1 1.8(4) . . . . ? N3 Cu1 N1 C10 -148(23) . . . . ? N4 Cu1 N1 C10 -3.6(5) . . . . ? N2 Cu1 N1 C10 -172.5(5) . . . . ? N1 Cu1 N2 C3 -139.3(5) . . . . ? N3 Cu1 N2 C3 40.9(5) . . . . ? N4 Cu1 N2 C3 -175.8(7) . . . . ? N1 Cu1 N2 C2 -11.4(4) . . . . ? N3 Cu1 N2 C2 168.8(4) . . . . ? N4 Cu1 N2 C2 -47.9(9) . . . . ? N1 Cu1 N3 C14 54(23) . . . . ? N4 Cu1 N3 C14 -90.1(4) . . . . ? N2 Cu1 N3 C14 78.6(4) . . . . ? N1 Cu1 N3 C6 177(100) . . . . ? N4 Cu1 N3 C6 32.2(5) . . . . ? N2 Cu1 N3 C6 -159.0(4) . . . . ? N1 Cu1 N3 C5 -67(23) . . . . ? N4 Cu1 N3 C5 148.7(4) . . . . ? N2 Cu1 N3 C5 -42.6(4) . . . . ? N1 Cu1 N4 C8 148.7(6) . . . . ? N3 Cu1 N4 C8 -31.6(6) . . . . ? N2 Cu1 N4 C8 -174.8(6) . . . . ? N1 Cu1 N4 C9 14.5(5) . . . . ? N3 Cu1 N4 C9 -165.9(5) . . . . ? N2 Cu1 N4 C9 51.0(10) . . . . ? C10 N1 C1 C13 0.1(9) . . . . ? Cu1 N1 C1 C13 -174.0(4) . . . . ? C10 N1 C1 C2 -177.5(6) . . . . ? Cu1 N1 C1 C2 8.4(7) . . . . ? C3 N2 C2 C1 149.6(5) . . . . ? Cu1 N2 C2 C1 18.3(6) . . . . ? N1 C1 C2 N2 -17.7(7) . . . . ? C13 C1 C2 N2 164.9(6) . . . . ? C2 N2 C3 C4 -179.7(5) . . . . ? Cu1 N2 C3 C4 -52.1(7) . . . . ? N2 C3 C4 C5 63.8(8) . . . . ? C14 N3 C5 C4 -55.7(7) . . . . ? C6 N3 C5 C4 -177.6(5) . . . . ? Cu1 N3 C5 C4 62.3(6) . . . . ? C3 C4 C5 N3 -72.7(7) . . . . ? C14 N3 C6 C7 63.8(8) . . . . ? C5 N3 C6 C7 -174.3(6) . . . . ? Cu1 N3 C6 C7 -55.6(7) . . . . ? N3 C6 C7 C8 73.8(9) . . . . ? C9 N4 C8 C7 -178.6(7) . . . . ? Cu1 N4 C8 C7 48.4(9) . . . . ? C6 C7 C8 N4 -66.1(9) . . . . ? C8 N4 C9 C10 -159.6(7) . . . . ? Cu1 N4 C9 C10 -22.3(9) . . . . ? C1 N1 C10 C11 0.5(10) . . . . ? Cu1 N1 C10 C11 174.6(5) . . . . ? C1 N1 C10 C9 177.5(6) . . . . ? Cu1 N1 C10 C9 -8.4(8) . . . . ? N4 C9 C10 N1 20.2(10) . . . . ? N4 C9 C10 C11 -163.1(7) . . . . ? N1 C10 C11 C12 -0.6(11) . . . . ? C9 C10 C11 C12 -177.1(7) . . . . ? C10 C11 C12 C13 0.0(10) . . . . ? C11 C12 C13 C1 0.6(9) . . . . ? N1 C1 C13 C12 -0.6(9) . . . . ? C2 C1 C13 C12 176.7(6) . . . . ? C6 N3 C14 C15 63.7(7) . . . . ? C5 N3 C14 C15 -54.7(7) . . . . ? Cu1 N3 C14 C15 -174.2(5) . . . . ? N3 C14 C15 C16 166.0(6) . . . . ? C17 N5 C16 C15 -164.1(8) . . . . ? C14 C15 C16 N5 -174.8(7) . . . . ? C16 N5 C17 O1 -1.7(14) . . . . ? C16 N5 C17 C18 -179.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.037 _refine_diff_density_min -2.027 _refine_diff_density_rms 0.167 #===END data_[Cu(L4c)](ClO4)2 _database_code_CSD 198030 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H33 Cl2 Cu N5 O9' _chemical_formula_weight 657.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 8.769(6) _cell_length_b 11.496(8) _cell_length_c 15.502(11) _cell_angle_alpha 69.236(14) _cell_angle_beta 80.586(18) _cell_angle_gamma 76.862(19) _cell_volume 1417.0(16) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 798 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 18.44 _exptl_crystal_description chunk _exptl_crystal_colour magenta _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 682 _exptl_absorpt_coefficient_mu 1.018 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6315 _diffrn_reflns_av_R_equivalents 0.1078 _diffrn_reflns_av_sigmaI/netI 0.1923 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 23.29 _reflns_number_total 3756 _reflns_number_gt 1540 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1100P)^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 3756 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1645 _refine_ls_R_factor_gt 0.0756 _refine_ls_wR_factor_ref 0.2166 _refine_ls_wR_factor_gt 0.1780 _refine_ls_goodness_of_fit_ref 0.834 _refine_ls_restrained_S_all 0.834 _refine_ls_shift/su_max 0.056 _refine_ls_shift/su_mean 0.007 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 0.68109(13) 0.86926(11) 0.77421(8) 0.0514(5) Uani 1 1 d . . . N1 N 0.6436(10) 0.8714(9) 0.6529(6) 0.058(2) Uani 1 1 d . . . N3 N 0.7290(9) 0.8622(8) 0.8997(5) 0.056(2) Uani 1 1 d . . . N4 N 0.8312(9) 0.9854(8) 0.6949(5) 0.062(2) Uani 1 1 d . . . H4C H 0.9281 0.9353 0.6965 0.074 Uiso 1 1 calc R . . N2 N 0.5630(10) 0.7232(8) 0.8197(6) 0.064(2) Uani 1 1 d . . . H2C H 0.6393 0.6526 0.8297 0.077 Uiso 1 1 calc R . . C9 C 0.7932(13) 1.0308(12) 0.5950(8) 0.083(4) Uani 1 1 d . . . H9A H 0.7229 1.1123 0.5812 0.100 Uiso 1 1 calc R . . H9B H 0.8890 1.0413 0.5540 0.100 Uiso 1 1 calc R . . C3 C 0.4635(13) 0.7035(11) 0.9068(8) 0.083(4) Uani 1 1 d . . . H3A H 0.4288 0.6233 0.9242 0.099 Uiso 1 1 calc R . . H3B H 0.3711 0.7701 0.8987 0.099 Uiso 1 1 calc R . . C2 C 0.4797(13) 0.7234(10) 0.7434(8) 0.072(4) Uani 1 1 d . . . H2A H 0.4766 0.6371 0.7490 0.087 Uiso 1 1 calc R . . H2B H 0.3725 0.7687 0.7471 0.087 Uiso 1 1 calc R . . C18 C 1.2277(13) 0.5843(9) 1.2690(8) 0.060(3) Uani 1 1 d . . . C19 C 1.1209(13) 0.5800(10) 1.3468(8) 0.065(3) Uani 1 1 d . . . H19 H 1.0171 0.5751 1.3452 0.078 Uiso 1 1 calc R . . C20 C 1.1695(16) 0.5830(11) 1.4259(8) 0.082(4) Uani 1 1 d . . . H20 H 1.0970 0.5818 1.4771 0.098 Uiso 1 1 calc R . . C21 C 1.3213(18) 0.5877(11) 1.4306(9) 0.088(4) Uani 1 1 d . . . H21 H 1.3529 0.5863 1.4854 0.106 Uiso 1 1 calc R . . C11 C 0.7192(16) 0.9275(16) 0.4919(10) 0.103(5) Uani 1 1 d . . . H11 H 0.7695 0.9769 0.4384 0.124 Uiso 1 1 calc R . . C12 C 0.6402(19) 0.8387(16) 0.4921(10) 0.109(5) Uani 1 1 d . . . H12 H 0.6395 0.8257 0.4363 0.130 Uiso 1 1 calc R . . Cl2 Cl 0.3086(4) 0.0902(4) 0.7767(2) 0.0830(10) Uani 1 1 d . . . C10 C 0.7184(13) 0.9386(12) 0.5792(9) 0.071(3) Uani 1 1 d . . . C13 C 0.5614(16) 0.7665(13) 0.5694(10) 0.093(4) Uani 1 1 d . . . H13 H 0.5082 0.7072 0.5657 0.112 Uiso 1 1 calc R . . C1 C 0.5632(14) 0.7849(11) 0.6538(9) 0.069(3) Uani 1 1 d . . . C23 C 1.3817(12) 0.5932(9) 1.2722(9) 0.074(3) Uani 1 1 d . . . H23 H 1.4532 0.5981 1.2203 0.089 Uiso 1 1 calc R . . C22 C 1.4295(16) 0.5947(12) 1.3532(11) 0.093(4) Uani 1 1 d . . . H22 H 1.5328 0.6004 1.3556 0.112 Uiso 1 1 calc R . . O1 O 1.2785(11) 0.5376(7) 1.1283(5) 0.086(3) Uani 1 1 d . . . C14 C 0.8792(13) 0.7660(9) 0.9236(7) 0.070(3) Uani 1 1 d . . . H14A H 0.9575 0.7858 0.8711 0.084 Uiso 1 1 calc R . . H14B H 0.8584 0.6832 0.9319 0.084 Uiso 1 1 calc R . . C7 C 0.8809(13) 1.0443(11) 0.8246(8) 0.074(4) Uani 1 1 d . . . H7A H 0.9051 1.1134 0.8389 0.089 Uiso 1 1 calc R . . H7B H 0.9738 0.9782 0.8327 0.089 Uiso 1 1 calc R . . C6 C 0.7486(13) 0.9928(10) 0.8938(7) 0.065(3) Uani 1 1 d . . . H6A H 0.7672 0.9897 0.9546 0.079 Uiso 1 1 calc R . . H6B H 0.6508 1.0514 0.8774 0.079 Uiso 1 1 calc R . . C8 C 0.8477(13) 1.0907(11) 0.7253(8) 0.084(4) Uani 1 1 d . . . H8A H 0.7514 1.1534 0.7170 0.101 Uiso 1 1 calc R . . H8B H 0.9326 1.1313 0.6870 0.101 Uiso 1 1 calc R . . C5 C 0.5992(14) 0.8277(12) 0.9700(7) 0.079(4) Uani 1 1 d . . . H5A H 0.5082 0.8947 0.9539 0.095 Uiso 1 1 calc R . . H5B H 0.6277 0.8248 1.0287 0.095 Uiso 1 1 calc R . . C15 C 0.9507(16) 0.7580(12) 1.0114(8) 0.108(5) Uani 1 1 d . . . H15A H 1.0522 0.7839 0.9926 0.129 Uiso 1 1 calc R . . H15B H 0.8831 0.8179 1.0385 0.129 Uiso 1 1 calc R . . C4 C 0.5511(16) 0.7036(13) 0.9838(8) 0.102(5) Uani 1 1 d . . . H4A H 0.4849 0.6811 1.0416 0.123 Uiso 1 1 calc R . . H4B H 0.6448 0.6385 0.9899 0.123 Uiso 1 1 calc R . . C16 C 0.9703(17) 0.6385(12) 1.0793(8) 0.110(5) Uani 1 1 d . . . H16A H 1.0403 0.5786 1.0532 0.132 Uiso 1 1 calc R . . H16B H 0.8694 0.6114 1.0978 0.132 Uiso 1 1 calc R . . O7 O 0.4686(9) 0.0649(8) 0.7525(6) 0.113(3) Uani 1 1 d . . . O9 O 0.2600(10) 0.0395(10) 0.8693(6) 0.122(3) Uani 1 1 d . . . O6 O 0.2345(12) 0.2082(10) 0.7340(8) 0.158(5) Uani 1 1 d . . . O8 O 0.2492(14) 0.0140(14) 0.7342(8) 0.175(5) Uani 1 1 d . . . Cl1 Cl 0.0873(4) 0.6842(4) 0.6930(3) 0.0956(12) Uani 1 1 d . . . O4 O -0.0667(10) 0.6756(8) 0.7346(7) 0.119(3) Uani 1 1 d . . . O3 O 0.1246(10) 0.8014(8) 0.6727(8) 0.146(4) Uani 1 1 d . . . O5 O 0.1813(15) 0.5936(14) 0.738(2) 0.40(2) Uani 1 1 d . . . O2 O 0.114(4) 0.658(3) 0.622(2) 0.51(3) Uani 1 1 d . . . N5 N 1.0345(12) 0.6364(8) 1.1613(6) 0.078(3) Uani 1 1 d . . . H5C H 0.9749 0.6712 1.1988 0.093 Uiso 1 1 calc R . . C17 C 1.1849(16) 0.5814(10) 1.1803(8) 0.064(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0507(8) 0.0606(9) 0.0422(8) -0.0172(7) -0.0079(6) -0.0059(6) N1 0.057(6) 0.059(6) 0.046(6) -0.008(5) -0.016(5) 0.004(5) N3 0.053(5) 0.071(6) 0.041(5) -0.019(5) -0.016(4) 0.002(5) N4 0.062(6) 0.060(6) 0.053(6) -0.008(5) -0.003(4) -0.007(5) N2 0.064(6) 0.059(6) 0.059(6) -0.007(5) -0.010(5) -0.006(4) C9 0.062(8) 0.096(10) 0.065(9) -0.004(8) 0.012(6) -0.014(7) C3 0.074(8) 0.087(9) 0.079(9) -0.011(8) 0.003(8) -0.033(7) C2 0.082(8) 0.060(8) 0.081(9) -0.015(7) -0.040(8) -0.016(7) C18 0.062(8) 0.051(7) 0.059(8) -0.008(6) -0.017(7) -0.005(6) C19 0.072(8) 0.074(8) 0.054(7) -0.022(7) -0.013(7) -0.017(6) C20 0.098(10) 0.093(9) 0.057(8) -0.020(7) -0.019(7) -0.022(8) C21 0.110(12) 0.087(9) 0.064(9) -0.009(8) -0.046(9) -0.011(9) C11 0.101(11) 0.140(14) 0.060(10) -0.034(10) -0.023(8) 0.009(10) C12 0.145(14) 0.130(14) 0.055(10) -0.045(11) -0.008(10) -0.011(11) Cl2 0.067(2) 0.106(3) 0.068(2) -0.034(2) -0.0117(18) 0.013(2) C10 0.065(8) 0.076(9) 0.058(9) -0.013(8) -0.017(7) 0.005(7) C13 0.122(12) 0.095(10) 0.083(10) -0.050(10) -0.046(9) 0.000(9) C1 0.081(8) 0.065(8) 0.076(10) -0.042(8) -0.037(7) 0.008(7) C23 0.047(7) 0.068(8) 0.097(10) -0.020(7) -0.017(7) 0.004(6) C22 0.072(9) 0.092(10) 0.113(12) -0.014(10) -0.050(9) -0.012(8) O1 0.120(8) 0.079(6) 0.053(5) -0.029(5) -0.005(5) 0.001(5) C14 0.095(9) 0.065(7) 0.057(7) -0.036(6) -0.040(7) 0.020(6) C7 0.079(9) 0.073(8) 0.077(9) -0.021(7) -0.034(7) -0.013(7) C6 0.084(8) 0.058(8) 0.058(7) -0.034(7) -0.028(7) 0.018(6) C8 0.083(9) 0.074(9) 0.102(11) -0.024(9) -0.021(8) -0.027(7) C5 0.086(9) 0.103(10) 0.039(7) -0.022(7) 0.002(7) -0.006(8) C15 0.154(13) 0.103(11) 0.077(9) -0.037(9) -0.074(9) 0.013(9) C4 0.123(12) 0.121(12) 0.054(8) -0.011(8) 0.020(8) -0.054(10) C16 0.178(14) 0.090(10) 0.073(9) -0.016(8) -0.087(10) -0.007(9) O7 0.045(5) 0.141(8) 0.139(8) -0.059(6) -0.003(5) 0.032(5) O9 0.100(7) 0.188(10) 0.063(6) -0.039(7) -0.002(5) -0.005(7) O6 0.120(9) 0.102(8) 0.190(11) -0.027(8) 0.026(8) 0.035(7) O8 0.158(10) 0.268(15) 0.146(10) -0.106(11) -0.011(8) -0.070(10) Cl1 0.060(2) 0.088(3) 0.153(4) -0.066(3) 0.005(2) -0.007(2) O4 0.074(6) 0.096(7) 0.181(10) -0.054(7) 0.013(6) -0.006(5) O3 0.085(7) 0.067(6) 0.290(14) -0.055(7) -0.020(7) -0.024(5) O5 0.067(8) 0.117(11) 0.84(5) 0.09(2) -0.094(18) -0.018(8) O2 0.69(5) 0.64(5) 0.49(4) -0.52(4) 0.42(4) -0.45(4) N5 0.115(8) 0.068(6) 0.052(6) -0.019(5) -0.047(6) 0.007(6) C17 0.090(10) 0.044(7) 0.049(8) -0.006(6) -0.030(7) 0.010(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.952(8) . ? Cu1 N3 2.026(8) . ? Cu1 N2 2.025(8) . ? Cu1 N4 2.033(8) . ? N1 C10 1.301(13) . ? N1 C1 1.339(12) . ? N3 C5 1.461(13) . ? N3 C6 1.519(12) . ? N3 C14 1.518(12) . ? N4 C8 1.489(12) . ? N4 C9 1.516(12) . ? N4 H4C 0.9100 . ? N2 C3 1.458(13) . ? N2 C2 1.488(11) . ? N2 H2C 0.9100 . ? C9 C10 1.472(15) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C3 C4 1.522(14) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2 C1 1.473(15) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C18 C23 1.387(13) . ? C18 C19 1.394(14) . ? C18 C17 1.496(14) . ? C19 C20 1.376(13) . ? C19 H19 0.9300 . ? C20 C21 1.359(15) . ? C20 H20 0.9300 . ? C21 C22 1.392(17) . ? C21 H21 0.9300 . ? C11 C12 1.357(18) . ? C11 C10 1.402(16) . ? C11 H11 0.9300 . ? C12 C13 1.373(17) . ? C12 H12 0.9300 . ? Cl2 O6 1.343(10) . ? Cl2 O7 1.383(8) . ? Cl2 O9 1.379(8) . ? Cl2 O8 1.484(11) . ? C13 C1 1.401(15) . ? C13 H13 0.9300 . ? C23 C22 1.394(15) . ? C23 H23 0.9300 . ? C22 H22 0.9300 . ? O1 C17 1.209(12) . ? C14 C15 1.555(13) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C7 C8 1.494(13) . ? C7 C6 1.517(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C5 C4 1.512(15) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C15 C16 1.397(15) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C16 N5 1.462(12) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? Cl1 O2 1.208(18) . ? Cl1 O5 1.240(14) . ? Cl1 O3 1.374(8) . ? Cl1 O4 1.407(9) . ? N5 C17 1.358(13) . ? N5 H5C 0.8600 . ? 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 N3 177.6(4) . . ? N1 Cu1 N2 82.7(4) . . ? N3 Cu1 N2 97.4(3) . . ? N1 Cu1 N4 81.6(4) . . ? N3 Cu1 N4 97.7(3) . . ? N2 Cu1 N4 159.7(4) . . ? C10 N1 C1 124.1(11) . . ? C10 N1 Cu1 119.1(8) . . ? C1 N1 Cu1 115.7(8) . . ? C5 N3 C6 107.1(9) . . ? C5 N3 C14 111.3(8) . . ? C6 N3 C14 111.3(7) . . ? C5 N3 Cu1 111.1(6) . . ? C6 N3 Cu1 109.0(6) . . ? C14 N3 Cu1 107.1(6) . . ? C8 N4 C9 112.4(9) . . ? C8 N4 Cu1 117.6(7) . . ? C9 N4 Cu1 108.8(6) . . ? C8 N4 H4C 105.7 . . ? C9 N4 H4C 105.7 . . ? Cu1 N4 H4C 105.7 . . ? C3 N2 C2 112.2(8) . . ? C3 N2 Cu1 119.0(7) . . ? C2 N2 Cu1 109.8(6) . . ? C3 N2 H2C 104.8 . . ? C2 N2 H2C 104.8 . . ? Cu1 N2 H2C 104.8 . . ? C10 C9 N4 110.0(9) . . ? C10 C9 H9A 109.7 . . ? N4 C9 H9A 109.7 . . ? C10 C9 H9B 109.7 . . ? N4 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N2 C3 C4 111.3(9) . . ? N2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? N2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C1 C2 N2 109.1(8) . . ? C1 C2 H2A 109.9 . . ? N2 C2 H2A 109.9 . . ? C1 C2 H2B 109.8 . . ? N2 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? C23 C18 C19 119.2(11) . . ? C23 C18 C17 117.4(11) . . ? C19 C18 C17 123.3(10) . . ? C20 C19 C18 119.9(10) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C21 C20 C19 121.2(12) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C22 120.0(12) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C12 C11 C10 114.3(15) . . ? C12 C11 H11 122.9 . . ? C10 C11 H11 122.9 . . ? C11 C12 C13 124.3(15) . . ? C11 C12 H12 117.8 . . ? C13 C12 H12 117.8 . . ? O6 Cl2 O7 115.7(6) . . ? O6 Cl2 O9 115.2(7) . . ? O7 Cl2 O9 116.1(6) . . ? O6 Cl2 O8 102.5(8) . . ? O7 Cl2 O8 101.5(7) . . ? O9 Cl2 O8 102.5(7) . . ? N1 C10 C11 122.1(12) . . ? N1 C10 C9 114.1(11) . . ? C11 C10 C9 123.7(14) . . ? C12 C13 C1 118.1(13) . . ? C12 C13 H13 121.0 . . ? C1 C13 H13 121.0 . . ? N1 C1 C13 117.0(13) . . ? N1 C1 C2 115.9(10) . . ? C13 C1 C2 127.0(12) . . ? C18 C23 C22 120.2(12) . . ? C18 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C22 C21 119.4(11) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? N3 C14 C15 115.9(9) . . ? N3 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? N3 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C8 C7 C6 115.1(8) . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? C6 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? N3 C6 C7 114.8(9) . . ? N3 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? N3 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? N4 C8 C7 111.5(9) . . ? N4 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N4 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? N3 C5 C4 116.6(10) . . ? N3 C5 H5A 108.1 . . ? C4 C5 H5A 108.1 . . ? N3 C5 H5B 108.1 . . ? C4 C5 H5B 108.1 . . ? H5A C5 H5B 107.3 . . ? C16 C15 C14 115.0(10) . . ? C16 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C5 C4 C3 115.1(10) . . ? C5 C4 H4A 108.5 . . ? C3 C4 H4A 108.5 . . ? C5 C4 H4B 108.5 . . ? C3 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? C15 C16 N5 113.0(10) . . ? C15 C16 H16A 109.0 . . ? N5 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? N5 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? O2 Cl1 O5 97(2) . . ? O2 Cl1 O3 107.1(13) . . ? O5 Cl1 O3 115.5(9) . . ? O2 Cl1 O4 113.3(16) . . ? O5 Cl1 O4 109.6(10) . . ? O3 Cl1 O4 113.7(6) . . ? C17 N5 C16 122.2(11) . . ? C17 N5 H5C 118.9 . . ? C16 N5 H5C 118.9 . . ? O1 C17 N5 122.8(11) . . ? O1 C17 C18 122.6(11) . . ? N5 C17 C18 114.6(11) . . ? 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 N3 Cu1 N1 C10 -74(10) . . . . ? N2 Cu1 N1 C10 -167.8(9) . . . . ? N4 Cu1 N1 C10 -0.7(8) . . . . ? N3 Cu1 N1 C1 94(10) . . . . ? N2 Cu1 N1 C1 0.6(7) . . . . ? N4 Cu1 N1 C1 167.8(8) . . . . ? N1 Cu1 N3 C5 -129(10) . . . . ? N2 Cu1 N3 C5 -36.0(8) . . . . ? N4 Cu1 N3 C5 157.5(7) . . . . ? N1 Cu1 N3 C6 113(10) . . . . ? N2 Cu1 N3 C6 -153.8(6) . . . . ? N4 Cu1 N3 C6 39.7(7) . . . . ? N1 Cu1 N3 C14 -7(10) . . . . ? N2 Cu1 N3 C14 85.7(7) . . . . ? N4 Cu1 N3 C14 -80.8(7) . . . . ? N1 Cu1 N4 C8 144.1(7) . . . . ? N3 Cu1 N4 C8 -38.3(7) . . . . ? N2 Cu1 N4 C8 -176.3(8) . . . . ? N1 Cu1 N4 C9 14.9(7) . . . . ? N3 Cu1 N4 C9 -167.4(7) . . . . ? N2 Cu1 N4 C9 54.6(12) . . . . ? N1 Cu1 N2 C3 -146.7(8) . . . . ? N3 Cu1 N2 C3 35.8(8) . . . . ? N4 Cu1 N2 C3 173.8(8) . . . . ? N1 Cu1 N2 C2 -15.5(7) . . . . ? N3 Cu1 N2 C2 167.0(7) . . . . ? N4 Cu1 N2 C2 -55.0(13) . . . . ? C8 N4 C9 C10 -157.8(9) . . . . ? Cu1 N4 C9 C10 -25.8(11) . . . . ? C2 N2 C3 C4 180.0(9) . . . . ? Cu1 N2 C3 C4 -49.9(12) . . . . ? C3 N2 C2 C1 161.0(10) . . . . ? Cu1 N2 C2 C1 26.3(11) . . . . ? C23 C18 C19 C20 -0.8(16) . . . . ? C17 C18 C19 C20 179.9(9) . . . . ? C18 C19 C20 C21 -1.3(17) . . . . ? C19 C20 C21 C22 2.6(19) . . . . ? C10 C11 C12 C13 2(2) . . . . ? C1 N1 C10 C11 1.1(17) . . . . ? Cu1 N1 C10 C11 168.5(9) . . . . ? C1 N1 C10 C9 177.8(9) . . . . ? Cu1 N1 C10 C9 -14.8(12) . . . . ? C12 C11 C10 N1 -2.1(18) . . . . ? C12 C11 C10 C9 -178.5(12) . . . . ? N4 C9 C10 N1 26.7(13) . . . . ? N4 C9 C10 C11 -156.6(11) . . . . ? C11 C12 C13 C1 -1(2) . . . . ? C10 N1 C1 C13 0.3(15) . . . . ? Cu1 N1 C1 C13 -167.5(8) . . . . ? C10 N1 C1 C2 -177.0(10) . . . . ? Cu1 N1 C1 C2 15.2(12) . . . . ? C12 C13 C1 N1 -0.6(17) . . . . ? C12 C13 C1 C2 176.3(12) . . . . ? N2 C2 C1 N1 -27.6(13) . . . . ? N2 C2 C1 C13 155.5(10) . . . . ? C19 C18 C23 C22 1.5(16) . . . . ? C17 C18 C23 C22 -179.2(10) . . . . ? C18 C23 C22 C21 -0.2(18) . . . . ? C20 C21 C22 C23 -2(2) . . . . ? C5 N3 C14 C15 -66.3(12) . . . . ? C6 N3 C14 C15 53.1(12) . . . . ? Cu1 N3 C14 C15 172.1(8) . . . . ? C5 N3 C6 C7 179.1(8) . . . . ? C14 N3 C6 C7 57.3(10) . . . . ? Cu1 N3 C6 C7 -60.6(9) . . . . ? C8 C7 C6 N3 75.5(12) . . . . ? C9 N4 C8 C7 178.5(9) . . . . ? Cu1 N4 C8 C7 51.1(11) . . . . ? C6 C7 C8 N4 -66.1(13) . . . . ? C6 N3 C5 C4 176.3(9) . . . . ? C14 N3 C5 C4 -61.8(11) . . . . ? Cu1 N3 C5 C4 57.4(11) . . . . ? N3 C14 C15 C16 122.7(13) . . . . ? N3 C5 C4 C3 -73.0(14) . . . . ? N2 C3 C4 C5 64.5(14) . . . . ? C14 C15 C16 N5 -178.7(11) . . . . ? C15 C16 N5 C17 -107.0(14) . . . . ? C16 N5 C17 O1 4.7(16) . . . . ? C16 N5 C17 C18 -177.9(9) . . . . ? C23 C18 C17 O1 29.9(15) . . . . ? C19 C18 C17 O1 -150.8(11) . . . . ? C23 C18 C17 N5 -147.6(10) . . . . ? C19 C18 C17 N5 31.8(14) . . . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.688 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.097