# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Mahammad Ali' 'Song Gao' 'H. Mayer-Figge' 'A. Ray' 'A.I. Sahmes' 'W.S. Sheldrick' _publ_contact_author_name 'Dr Mahammad Ali' _publ_contact_author_address ; Department of Chemistry Jadavpur University Faculty of Science Kolkata 700 032 INDIA ; _publ_contact_author_email M_ALI2062@YAHOO.COM _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Synthesis, crystal structure, EPR and magnetic property of a cyano-bridged CuII-NiII heterobimetallic complex: an unusual structure with long distance ferromagnetic exchange through hydrogen bonding ; data_s2 _database_code_depnum_ccdc_archive 'CCDC 223767' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H40 N4 O9 Cl2' _chemical_formula_weight 503.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.210(2) _cell_length_b 8.8436(18) _cell_length_c 25.809(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.39(3) _cell_angle_gamma 90.00 _cell_volume 2531.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 15.0 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.306 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.72358 _exptl_absorpt_correction_T_max 0.74869 _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 'Siemens P4 4-circle-diffractometer' _diffrn_measurement_method 'Profile fitted' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 20 _diffrn_reflns_number 3500 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.1182 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 22.50 _reflns_number_total 3302 _reflns_number_gt 1605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens R3m/V' _computing_cell_refinement 'Siemens R3m/V' _computing_data_reduction XDISK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL-PLUS (VMS)' _computing_publication_material SHELXL-97 _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^)+(0.0600P)^2^+2.4114P] 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 3302 _refine_ls_number_parameters 294 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1742 _refine_ls_R_factor_gt 0.0737 _refine_ls_wR_factor_ref 0.1794 _refine_ls_wR_factor_gt 0.1400 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.018 _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 N1 N 0.2968(5) 1.3197(6) 0.2018(2) 0.0400(15) Uani 1 1 d D . . H1 H 0.261(5) 1.225(3) 0.207(2) 0.048 Uiso 1 1 d D . . N2 N 0.3677(5) 1.2416(6) 0.1050(2) 0.0418(15) Uani 1 1 d . . . H21 H 0.3233 1.2985 0.1239 0.08(2) Uiso 1 1 calc R . . H22 H 0.3728 1.2924 0.0752 0.08(2) Uiso 1 1 calc R . . N3 N 0.1018(5) 1.2042(6) 0.1012(2) 0.0401(15) Uani 1 1 d D . . H3 H 0.095(5) 1.142(6) 0.1307(15) 0.048 Uiso 1 1 d D . . N4 N 0.0851(5) 1.4871(6) 0.1464(2) 0.0387(15) Uani 1 1 d . . . H41 H 0.1271 1.4198 0.1302 0.043(14) Uiso 1 1 calc R . . H42 H 0.1181 1.5785 0.1427 0.043(14) Uiso 1 1 calc R . . C1 C 0.4261(6) 1.3004(8) 0.2251(3) 0.047(2) Uani 1 1 d . . . H11 H 0.4661 1.3984 0.2235 0.056 Uiso 1 1 calc R . . C11 C 0.4417(6) 1.2518(8) 0.2821(3) 0.058(2) Uani 1 1 d . . . H111 H 0.4003 1.3216 0.3017 0.087 Uiso 1 1 calc R . . H112 H 0.5260 1.2508 0.2960 0.087 Uiso 1 1 calc R . . H113 H 0.4088 1.1523 0.2846 0.087 Uiso 1 1 calc R . . C2 C 0.4862(6) 1.1900(8) 0.1924(3) 0.0442(19) Uani 1 1 d . . . H23 H 0.4438 1.0944 0.1924 0.053 Uiso 1 1 calc R . . H24 H 0.5676 1.1730 0.2101 0.053 Uiso 1 1 calc R . . C3 C 0.4944(6) 1.2305(8) 0.1355(3) 0.048(2) Uani 1 1 d . . . C31 C 0.5667(6) 1.1097(9) 0.1103(3) 0.066(2) Uani 1 1 d . . . H311 H 0.5331 1.0116 0.1150 0.100 Uiso 1 1 calc R . . H312 H 0.6493 1.1119 0.1266 0.100 Uiso 1 1 calc R . . H313 H 0.5626 1.1303 0.0736 0.100 Uiso 1 1 calc R . . C32 C 0.5503(7) 1.3868(9) 0.1304(3) 0.065(2) Uani 1 1 d . . . H321 H 0.5654 1.4012 0.0950 0.098 Uiso 1 1 calc R . . H322 H 0.6248 1.3939 0.1539 0.098 Uiso 1 1 calc R . . H323 H 0.4957 1.4633 0.1390 0.098 Uiso 1 1 calc R . . C4 C 0.2999(6) 1.0994(8) 0.0908(3) 0.049(2) Uani 1 1 d . . . H43 H 0.2972 1.0395 0.1221 0.059 Uiso 1 1 calc R . . H44 H 0.3414 1.0409 0.0671 0.059 Uiso 1 1 calc R . . C5 C 0.1725(6) 1.1323(9) 0.0648(3) 0.057(2) Uani 1 1 d . . . H52 H 0.1751 1.1982 0.0349 0.069 Uiso 1 1 calc R . . H53 H 0.1338 1.0386 0.0521 0.069 Uiso 1 1 calc R . . C6 C -0.0289(6) 1.2168(8) 0.0793(3) 0.0453(19) Uani 1 1 d . . . H6 H -0.0346 1.2576 0.0437 0.054 Uiso 1 1 calc R . . C61 C -0.0950(7) 1.0648(8) 0.0761(3) 0.066(2) Uani 1 1 d . . . H611 H -0.0539 0.9941 0.0567 0.099 Uiso 1 1 calc R . . H612 H -0.1761 1.0784 0.0588 0.099 Uiso 1 1 calc R . . H613 H -0.0966 1.0266 0.1109 0.099 Uiso 1 1 calc R . . C7 C -0.0923(6) 1.3275(8) 0.1121(3) 0.0431(18) Uani 1 1 d . . . H71 H -0.0881 1.2860 0.1471 0.052 Uiso 1 1 calc R . . H72 H -0.1768 1.3315 0.0971 0.052 Uiso 1 1 calc R . . C8 C -0.0442(6) 1.4905(8) 0.1170(3) 0.0409(18) Uani 1 1 d . . . C81 C -0.0343(6) 1.5639(9) 0.0644(3) 0.060(2) Uani 1 1 d . . . H811 H 0.0214 1.5076 0.0470 0.090 Uiso 1 1 calc R . . H812 H -0.0059 1.6658 0.0700 0.090 Uiso 1 1 calc R . . H813 H -0.1120 1.5644 0.0432 0.090 Uiso 1 1 calc R . . C82 C -0.1234(6) 1.5876(8) 0.1472(3) 0.058(2) Uani 1 1 d . . . H821 H -0.2015 1.5998 0.1268 0.087 Uiso 1 1 calc R . . H822 H -0.0866 1.6850 0.1541 0.087 Uiso 1 1 calc R . . H823 H -0.1317 1.5391 0.1798 0.087 Uiso 1 1 calc R . . C9 C 0.1037(6) 1.4499(8) 0.2030(2) 0.0455(19) Uani 1 1 d . . . H91 H 0.0679 1.3523 0.2082 0.055 Uiso 1 1 calc R . . H92 H 0.0639 1.5251 0.2218 0.055 Uiso 1 1 calc R . . C10 C 0.2373(6) 1.4460(8) 0.2243(3) 0.049(2) Uani 1 1 d . . . H101 H 0.2745 1.5402 0.2160 0.059 Uiso 1 1 calc R . . H102 H 0.2476 1.4358 0.2621 0.059 Uiso 1 1 calc R . . Cl1 Cl 0.16696(19) 0.8866(2) 0.21284(8) 0.0508(6) Uani 1 1 d . . . O11 O 0.1551(7) 0.8151(7) 0.1640(2) 0.108(2) Uani 1 1 d . . . O12 O 0.1337(7) 0.7928(6) 0.2513(2) 0.106(2) Uani 1 1 d . . . O13 O 0.1028(7) 1.0256(7) 0.2090(2) 0.113(3) Uani 1 1 d . . . O14 O 0.2866(6) 0.9269(10) 0.2262(3) 0.159(4) Uani 1 1 d . . . Cl2 Cl 0.3112(2) 0.6709(2) 0.04810(9) 0.0622(6) Uani 1 1 d . . . O21 O 0.3317(7) 0.6144(9) -0.0014(3) 0.141(3) Uani 1 1 d . . . O22 O 0.2125(6) 0.7729(7) 0.0393(3) 0.101(2) Uani 1 1 d . . . O23 O 0.4164(5) 0.7448(7) 0.0707(3) 0.108(2) Uani 1 1 d . . . O24 O 0.2816(6) 0.5531(7) 0.0796(3) 0.110(3) Uani 1 1 d . . . OW O 0.3780(6) 0.3014(8) -0.0060(3) 0.111(2) 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 N1 0.044(4) 0.029(3) 0.045(4) -0.004(3) -0.001(3) -0.004(3) N2 0.041(4) 0.037(4) 0.046(4) 0.001(3) 0.004(3) 0.002(3) N3 0.038(4) 0.048(4) 0.034(4) -0.002(3) 0.005(3) 0.001(3) N4 0.032(3) 0.035(4) 0.049(4) 0.000(3) 0.004(3) -0.005(3) C1 0.038(5) 0.044(5) 0.053(5) -0.004(4) -0.007(4) -0.002(4) C11 0.061(5) 0.058(5) 0.050(5) 0.001(4) -0.005(4) 0.010(4) C2 0.033(4) 0.039(4) 0.057(5) 0.010(4) -0.003(4) 0.003(4) C3 0.034(4) 0.044(5) 0.067(5) 0.010(4) 0.012(4) 0.007(4) C31 0.044(5) 0.078(6) 0.078(6) -0.011(5) 0.011(4) 0.015(5) C32 0.060(5) 0.058(5) 0.079(6) 0.011(5) 0.013(5) -0.015(5) C4 0.050(5) 0.047(5) 0.053(5) -0.017(4) 0.013(4) -0.003(4) C5 0.048(5) 0.072(6) 0.050(5) -0.021(4) 0.004(4) -0.008(4) C6 0.042(5) 0.054(5) 0.038(4) -0.003(4) 0.002(4) 0.000(4) C61 0.059(6) 0.072(6) 0.065(6) -0.015(5) 0.001(5) -0.015(5) C7 0.027(4) 0.051(5) 0.048(5) 0.003(4) -0.004(3) -0.004(4) C8 0.031(4) 0.052(5) 0.040(4) -0.002(4) 0.005(3) 0.005(4) C81 0.047(5) 0.077(6) 0.056(5) 0.015(5) 0.007(4) -0.003(4) C82 0.051(5) 0.061(6) 0.060(5) 0.009(4) 0.004(4) 0.014(4) C9 0.050(5) 0.049(5) 0.037(5) 0.002(4) 0.004(4) 0.003(4) C10 0.049(5) 0.051(5) 0.047(5) -0.007(4) 0.005(4) 0.002(4) Cl1 0.0619(14) 0.0427(12) 0.0497(12) 0.0004(11) 0.0145(10) -0.0053(11) O11 0.203(8) 0.072(4) 0.053(4) -0.022(4) 0.032(4) -0.032(5) O12 0.190(7) 0.056(4) 0.091(5) 0.013(4) 0.082(5) 0.002(4) O13 0.174(7) 0.075(5) 0.099(5) 0.030(4) 0.048(5) 0.053(5) O14 0.072(5) 0.205(9) 0.189(9) 0.007(7) -0.021(5) -0.055(6) Cl2 0.0644(15) 0.0517(13) 0.0712(16) 0.0007(13) 0.0122(12) -0.0076(12) O21 0.173(8) 0.154(7) 0.108(6) -0.039(5) 0.060(6) -0.011(6) O22 0.097(5) 0.078(5) 0.120(6) 0.029(4) -0.013(4) 0.027(4) O23 0.069(4) 0.088(5) 0.157(6) -0.017(5) -0.016(4) -0.013(4) O24 0.099(5) 0.076(5) 0.165(7) 0.069(5) 0.051(5) 0.019(4) OW 0.102(5) 0.127(6) 0.112(5) 0.027(5) 0.043(4) 0.000(5) _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 N1 C10 1.463(8) . ? N1 C1 1.496(8) . ? N1 H1 0.948(10) . ? N2 C4 1.488(8) . ? N2 C3 1.523(8) . ? N2 H21 0.9000 . ? N2 H22 0.9000 . ? N3 C5 1.461(8) . ? N3 C6 1.496(8) . ? N3 H3 0.950(10) . ? N4 C9 1.481(7) . ? N4 C8 1.535(8) . ? N4 H41 0.9000 . ? N4 H42 0.9000 . ? C1 C2 1.511(9) . ? C1 C11 1.517(9) . ? C1 H11 0.9800 . ? C11 H111 0.9600 . ? C11 H112 0.9600 . ? C11 H113 0.9600 . ? C2 C3 1.527(9) . ? C2 H23 0.9700 . ? C2 H24 0.9700 . ? C3 C32 1.531(9) . ? C3 C31 1.542(9) . ? C31 H311 0.9600 . ? C31 H312 0.9600 . ? C31 H313 0.9600 . ? C32 H321 0.9600 . ? C32 H322 0.9600 . ? C32 H323 0.9600 . ? C4 C5 1.515(9) . ? C4 H43 0.9700 . ? C4 H44 0.9700 . ? C5 H52 0.9700 . ? C5 H53 0.9700 . ? C6 C61 1.531(9) . ? C6 C7 1.534(9) . ? C6 H6 0.9800 . ? C61 H611 0.9600 . ? C61 H612 0.9600 . ? C61 H613 0.9600 . ? C7 C8 1.538(9) . ? C7 H71 0.9700 . ? C7 H72 0.9700 . ? C8 C81 1.522(9) . ? C8 C82 1.529(9) . ? C81 H811 0.9600 . ? C81 H812 0.9600 . ? C81 H813 0.9600 . ? C82 H821 0.9600 . ? C82 H822 0.9600 . ? C82 H823 0.9600 . ? C9 C10 1.519(9) . ? C9 H91 0.9700 . ? C9 H92 0.9700 . ? C10 H101 0.9700 . ? C10 H102 0.9700 . ? Cl1 O14 1.382(7) . ? Cl1 O12 1.387(5) . ? Cl1 O11 1.398(5) . ? Cl1 O13 1.421(6) . ? Cl2 O24 1.391(6) . ? Cl2 O23 1.399(6) . ? Cl2 O22 1.420(6) . ? Cl2 O21 1.421(7) . ? 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 C10 N1 C1 113.5(5) . . ? C10 N1 H1 113(4) . . ? C1 N1 H1 104(4) . . ? C4 N2 C3 118.5(5) . . ? C4 N2 H21 107.7 . . ? C3 N2 H21 107.7 . . ? C4 N2 H22 107.7 . . ? C3 N2 H22 107.7 . . ? H21 N2 H22 107.1 . . ? C5 N3 C6 112.5(5) . . ? C5 N3 H3 112(4) . . ? C6 N3 H3 99(4) . . ? C9 N4 C8 118.6(5) . . ? C9 N4 H41 107.7 . . ? C8 N4 H41 107.7 . . ? C9 N4 H42 107.7 . . ? C8 N4 H42 107.7 . . ? H41 N4 H42 107.1 . . ? N1 C1 C2 109.6(5) . . ? N1 C1 C11 112.9(6) . . ? C2 C1 C11 111.1(6) . . ? N1 C1 H11 107.7 . . ? C2 C1 H11 107.7 . . ? C11 C1 H11 107.7 . . ? C1 C11 H111 109.5 . . ? C1 C11 H112 109.5 . . ? H111 C11 H112 109.5 . . ? C1 C11 H113 109.5 . . ? H111 C11 H113 109.5 . . ? H112 C11 H113 109.5 . . ? C1 C2 C3 118.6(6) . . ? C1 C2 H23 107.7 . . ? C3 C2 H23 107.7 . . ? C1 C2 H24 107.7 . . ? C3 C2 H24 107.7 . . ? H23 C2 H24 107.1 . . ? N2 C3 C2 109.3(5) . . ? N2 C3 C32 105.0(5) . . ? C2 C3 C32 112.2(6) . . ? N2 C3 C31 109.5(6) . . ? C2 C3 C31 110.6(6) . . ? C32 C3 C31 110.0(6) . . ? C3 C31 H311 109.5 . . ? C3 C31 H312 109.5 . . ? H311 C31 H312 109.5 . . ? C3 C31 H313 109.5 . . ? H311 C31 H313 109.5 . . ? H312 C31 H313 109.5 . . ? C3 C32 H321 109.5 . . ? C3 C32 H322 109.5 . . ? H321 C32 H322 109.5 . . ? C3 C32 H323 109.5 . . ? H321 C32 H323 109.5 . . ? H322 C32 H323 109.5 . . ? N2 C4 C5 111.2(6) . . ? N2 C4 H43 109.4 . . ? C5 C4 H43 109.4 . . ? N2 C4 H44 109.4 . . ? C5 C4 H44 109.4 . . ? H43 C4 H44 108.0 . . ? N3 C5 C4 111.3(6) . . ? N3 C5 H52 109.4 . . ? C4 C5 H52 109.4 . . ? N3 C5 H53 109.4 . . ? C4 C5 H53 109.4 . . ? H52 C5 H53 108.0 . . ? N3 C6 C61 113.3(6) . . ? N3 C6 C7 110.2(5) . . ? C61 C6 C7 109.3(6) . . ? N3 C6 H6 108.0 . . ? C61 C6 H6 108.0 . . ? C7 C6 H6 108.0 . . ? C6 C61 H611 109.5 . . ? C6 C61 H612 109.5 . . ? H611 C61 H612 109.5 . . ? C6 C61 H613 109.5 . . ? H611 C61 H613 109.5 . . ? H612 C61 H613 109.5 . . ? C6 C7 C8 117.3(6) . . ? C6 C7 H71 108.0 . . ? C8 C7 H71 108.0 . . ? C6 C7 H72 108.0 . . ? C8 C7 H72 108.0 . . ? H71 C7 H72 107.2 . . ? C81 C8 C82 109.8(6) . . ? C81 C8 N4 105.2(5) . . ? C82 C8 N4 109.5(5) . . ? C81 C8 C7 113.4(6) . . ? C82 C8 C7 110.3(6) . . ? N4 C8 C7 108.5(5) . . ? C8 C81 H811 109.5 . . ? C8 C81 H812 109.5 . . ? H811 C81 H812 109.5 . . ? C8 C81 H813 109.5 . . ? H811 C81 H813 109.5 . . ? H812 C81 H813 109.5 . . ? C8 C82 H821 109.5 . . ? C8 C82 H822 109.5 . . ? H821 C82 H822 109.5 . . ? C8 C82 H823 109.5 . . ? H821 C82 H823 109.5 . . ? H822 C82 H823 109.5 . . ? N4 C9 C10 110.6(6) . . ? N4 C9 H91 109.5 . . ? C10 C9 H91 109.5 . . ? N4 C9 H92 109.5 . . ? C10 C9 H92 109.5 . . ? H91 C9 H92 108.1 . . ? N1 C10 C9 110.9(6) . . ? N1 C10 H101 109.5 . . ? C9 C10 H101 109.5 . . ? N1 C10 H102 109.5 . . ? C9 C10 H102 109.5 . . ? H101 C10 H102 108.1 . . ? O14 Cl1 O12 109.2(5) . . ? O14 Cl1 O11 107.6(5) . . ? O12 Cl1 O11 112.0(4) . . ? O14 Cl1 O13 104.9(5) . . ? O12 Cl1 O13 112.4(4) . . ? O11 Cl1 O13 110.4(4) . . ? O24 Cl2 O23 111.3(5) . . ? O24 Cl2 O22 108.8(4) . . ? O23 Cl2 O22 111.1(4) . . ? O24 Cl2 O21 110.3(5) . . ? O23 Cl2 O21 107.6(5) . . ? O22 Cl2 O21 107.7(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.410 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.059 data_s1 _database_code_depnum_ccdc_archive 'CCDC 231317' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H36 N8 Ni Cu' _chemical_formula_weight 510.82 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' Ni Ni 0.3393 1.1124 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.140(9) _cell_length_b 12.002(4) _cell_length_c 14.286(5) _cell_angle_alpha 90.00 _cell_angle_beta 115.62(4) _cell_angle_gamma 90.00 _cell_volume 2340.8(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 1.736 _exptl_absorpt_correction_type Empirical _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 'Siemens P4 4-circle-diffractometer' _diffrn_measurement_method 'Profile fitted' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 20 _diffrn_reflns_number 3214 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2570 _reflns_number_gt 1790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens R3m/V' _computing_cell_refinement 'Siemens R3m/V' _computing_data_reduction XDISK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL-PLUS (VMS)' _computing_publication_material SHELXL-97 _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^)+(0.1124P)^2^+2.5482P] 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 2570 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1822 _refine_ls_wR_factor_gt 0.1568 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.0000 -0.27678(6) 0.2500 0.0286(3) Uani 1 2 d S . . Ni1 Ni 0.0000 0.14358(7) 0.2500 0.0343(3) Uani 1 2 d S . . N1 N -0.0681(3) -0.2861(3) 0.3465(3) 0.0321(8) Uani 1 1 d . . . H1 H -0.0500 -0.2232 0.3858 0.035(14) Uiso 1 1 calc R . . N2 N -0.1051(3) -0.3835(3) 0.1390(3) 0.0312(8) Uani 1 1 d . . . H2 H -0.0882 -0.4542 0.1632 0.036(14) Uiso 1 1 calc R . . C1 C -0.1788(4) -0.2858(4) 0.2973(4) 0.0363(10) Uani 1 1 d . . . C11 C -0.2162(5) -0.3018(6) 0.3816(4) 0.0506(14) Uani 1 1 d . . . H111 H -0.1972 -0.3740 0.4127 0.076 Uiso 1 1 calc R . . H112 H -0.2863 -0.2957 0.3505 0.076 Uiso 1 1 calc R . . H113 H -0.1883 -0.2454 0.4340 0.076 Uiso 1 1 calc R . . C12 C -0.2114(5) -0.1695(5) 0.2503(4) 0.0469(13) Uani 1 1 d . . . H121 H -0.1898 -0.1569 0.1972 0.070 Uiso 1 1 calc R . . H122 H -0.1833 -0.1142 0.3037 0.070 Uiso 1 1 calc R . . H123 H -0.2816 -0.1646 0.2208 0.070 Uiso 1 1 calc R . . C2 C -0.2210(4) -0.3782(4) 0.2173(4) 0.0397(11) Uani 1 1 d . . . H21 H -0.2904 -0.3835 0.1994 0.048 Uiso 1 1 calc R . . H22 H -0.1913 -0.4477 0.2507 0.048 Uiso 1 1 calc R . . C3 C -0.2101(4) -0.3703(4) 0.1160(4) 0.0370(11) Uani 1 1 d . . . H3 H -0.2313 -0.2959 0.0867 0.044 Uiso 1 1 calc R . . C31 C -0.2752(5) -0.4559(6) 0.0378(5) 0.0568(16) Uani 1 1 d . . . H311 H -0.3421 -0.4440 0.0251 0.085 Uiso 1 1 calc R . . H312 H -0.2553 -0.5295 0.0650 0.085 Uiso 1 1 calc R . . H313 H -0.2691 -0.4481 -0.0260 0.085 Uiso 1 1 calc R . . C4 C -0.0226(4) -0.3780(4) 0.4192(4) 0.0374(11) Uani 1 1 d . . . H41 H -0.0486 -0.4487 0.3856 0.045 Uiso 1 1 calc R . . H42 H -0.0368 -0.3709 0.4789 0.045 Uiso 1 1 calc R . . C5 C 0.0861(4) -0.3737(5) 0.4531(4) 0.0397(11) Uani 1 1 d . . . H51 H 0.1123 -0.3039 0.4884 0.048 Uiso 1 1 calc R . . H52 H 0.1178 -0.4343 0.5008 0.048 Uiso 1 1 calc R . . C6 C 0.0000 -0.0120(4) 0.2500 0.0251(12) Uani 1 2 d S . . N6 N 0.0000 -0.1068(6) 0.2500 0.0415(14) Uani 1 2 d S . . C7 C 0.0011(5) 0.1448(4) 0.1193(4) 0.0473(14) Uani 1 1 d . . . N7 N 0.0021(5) 0.1469(5) 0.0402(4) 0.0705(17) Uani 1 1 d . . . C8 C 0.0000 0.3011(6) 0.2500 0.0360(14) Uani 1 2 d S . . N8 N 0.0000 0.3952(6) 0.2500 0.069(2) Uani 1 2 d S . . 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 0.0298(5) 0.0286(4) 0.0292(4) 0.000 0.0145(3) 0.000 Ni1 0.0347(6) 0.0290(4) 0.0391(5) 0.000 0.0159(4) 0.000 N1 0.031(2) 0.0376(19) 0.0288(18) 0.0010(15) 0.0136(16) -0.0004(17) N2 0.029(2) 0.0307(17) 0.0306(18) -0.0023(15) 0.0099(16) -0.0003(17) C1 0.032(3) 0.040(2) 0.041(2) 0.001(2) 0.020(2) 0.003(2) C11 0.041(3) 0.072(4) 0.047(3) 0.002(3) 0.027(3) 0.001(3) C12 0.040(3) 0.050(3) 0.052(3) 0.006(3) 0.020(3) 0.013(3) C2 0.032(3) 0.047(3) 0.043(3) -0.001(2) 0.018(2) -0.008(2) C3 0.025(3) 0.041(2) 0.038(2) -0.001(2) 0.007(2) -0.002(2) C31 0.034(3) 0.083(4) 0.050(3) -0.019(3) 0.016(3) -0.016(3) C4 0.036(3) 0.043(2) 0.033(2) 0.006(2) 0.015(2) 0.003(2) C5 0.034(3) 0.053(3) 0.031(2) 0.008(2) 0.013(2) 0.005(2) C6 0.035(4) 0.014(2) 0.029(3) 0.000 0.017(3) 0.000 N6 0.044(4) 0.046(3) 0.042(3) 0.000 0.025(3) 0.000 C7 0.051(4) 0.046(3) 0.052(3) 0.009(2) 0.029(3) 0.005(2) N7 0.074(4) 0.088(4) 0.058(3) 0.026(3) 0.036(3) 0.011(3) C8 0.027(4) 0.034(3) 0.038(3) 0.000 0.006(3) 0.000 N8 0.089(7) 0.025(3) 0.073(5) 0.000 0.015(5) 0.000 _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 N6 2.041(7) . ? Cu1 N1 2.052(4) 2 ? Cu1 N1 2.052(4) . ? Cu1 N2 2.123(4) . ? Cu1 N2 2.123(4) 2 ? Ni1 C6 1.868(5) . ? Ni1 C7 1.874(6) . ? Ni1 C7 1.874(6) 2 ? Ni1 C8 1.891(7) . ? N1 C4 1.466(6) . ? N1 C1 1.511(7) . ? N1 H1 0.9100 . ? N2 C5 1.468(6) 2 ? N2 C3 1.485(6) . ? N2 H2 0.9100 . ? C1 C2 1.521(7) . ? C1 C12 1.535(7) . ? C1 C11 1.549(7) . ? C11 H111 0.9600 . ? C11 H112 0.9600 . ? C11 H113 0.9600 . ? C12 H121 0.9600 . ? C12 H122 0.9600 . ? C12 H123 0.9600 . ? C2 C3 1.529(7) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C3 C31 1.524(7) . ? C3 H3 0.9800 . ? C31 H311 0.9600 . ? C31 H312 0.9600 . ? C31 H313 0.9600 . ? C4 C5 1.503(7) . ? C4 H41 0.9700 . ? C4 H42 0.9700 . ? C5 N2 1.468(6) 2 ? C5 H51 0.9700 . ? C5 H52 0.9700 . ? C6 N6 1.137(9) . ? C7 N7 1.138(7) . ? C8 N8 1.129(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Cu1 N1 93.13(11) . 2 ? N6 Cu1 N1 93.13(11) . . ? N1 Cu1 N1 173.7(2) 2 . ? N6 Cu1 N2 127.11(11) . . ? N1 Cu1 N2 84.12(16) 2 . ? N1 Cu1 N2 92.09(16) . . ? N6 Cu1 N2 127.11(11) . 2 ? N1 Cu1 N2 92.09(16) 2 2 ? N1 Cu1 N2 84.12(16) . 2 ? N2 Cu1 N2 105.8(2) . 2 ? C6 Ni1 C7 90.45(16) . . ? C6 Ni1 C7 90.45(16) . 2 ? C7 Ni1 C7 179.1(3) . 2 ? C6 Ni1 C8 180.000(1) . . ? C7 Ni1 C8 89.55(16) . . ? C7 Ni1 C8 89.55(16) 2 . ? C4 N1 C1 114.7(4) . . ? C4 N1 Cu1 107.3(3) . . ? C1 N1 Cu1 117.7(3) . . ? C4 N1 H1 105.3 . . ? C1 N1 H1 105.3 . . ? Cu1 N1 H1 105.3 . . ? C5 N2 C3 113.5(4) 2 . ? C5 N2 Cu1 104.3(3) 2 . ? C3 N2 Cu1 119.1(3) . . ? C5 N2 H2 106.4 2 . ? C3 N2 H2 106.4 . . ? Cu1 N2 H2 106.4 . . ? N1 C1 C2 111.7(4) . . ? N1 C1 C12 106.8(4) . . ? C2 C1 C12 112.5(4) . . ? N1 C1 C11 110.0(4) . . ? C2 C1 C11 108.5(4) . . ? C12 C1 C11 107.2(4) . . ? C1 C11 H111 109.5 . . ? C1 C11 H112 109.5 . . ? H111 C11 H112 109.5 . . ? C1 C11 H113 109.5 . . ? H111 C11 H113 109.5 . . ? H112 C11 H113 109.5 . . ? C1 C12 H121 109.5 . . ? C1 C12 H122 109.5 . . ? H121 C12 H122 109.5 . . ? C1 C12 H123 109.5 . . ? H121 C12 H123 109.5 . . ? H122 C12 H123 109.5 . . ? C1 C2 C3 118.9(4) . . ? C1 C2 H21 107.6 . . ? C3 C2 H21 107.6 . . ? C1 C2 H22 107.6 . . ? C3 C2 H22 107.6 . . ? H21 C2 H22 107.0 . . ? N2 C3 C31 112.4(4) . . ? N2 C3 C2 109.1(4) . . ? C31 C3 C2 110.6(4) . . ? N2 C3 H3 108.2 . . ? C31 C3 H3 108.2 . . ? C2 C3 H3 108.2 . . ? C3 C31 H311 109.5 . . ? C3 C31 H312 109.5 . . ? H311 C31 H312 109.5 . . ? C3 C31 H313 109.5 . . ? H311 C31 H313 109.5 . . ? H312 C31 H313 109.5 . . ? N1 C4 C5 108.5(4) . . ? N1 C4 H41 110.0 . . ? C5 C4 H41 110.0 . . ? N1 C4 H42 110.0 . . ? C5 C4 H42 110.0 . . ? H41 C4 H42 108.4 . . ? N2 C5 C4 108.7(4) 2 . ? N2 C5 H51 109.9 2 . ? C4 C5 H51 109.9 . . ? N2 C5 H52 109.9 2 . ? C4 C5 H52 109.9 . . ? H51 C5 H52 108.3 . . ? N6 C6 Ni1 180.0 . . ? C6 N6 Cu1 180.0 . . ? N7 C7 Ni1 179.2(6) . . ? N8 C8 Ni1 180.000(1) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.620 _refine_diff_density_min -0.987 _refine_diff_density_rms 0.123