# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Chaudhuri, N. R.' 'Das, D.' 'Ghosh, A.' 'Keng, T.-C.' 'Laskar, I. R.' 'Lu, T.-H.' 'Mostafa, G.' 'Wang, J.-C.' _publ_contact_author_name 'Dr N R Chaudhuri' _publ_contact_author_address ; Dr N R Chaudhuri Indian Association for the Cultivation of Science Calcutta INDIA ; data_1 _database_code_CSD 153398 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H40 N6 Ni O4' _chemical_formula_weight 439.25 _chemical_melting_point ? _chemical_compound_source ? 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' 'Ni' 'Ni' 0.3393 1.1124 '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' 'N' 'N' 0.0061 0.0033 '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 7.4721(10) _cell_length_b 7.5310(10) _cell_length_c 11.0761(9) _cell_angle_alpha 93.4149(8) _cell_angle_beta 102.0416(10) _cell_angle_gamma 100.4858(10) _cell_volume 596.29(12) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 238 _exptl_absorpt_coefficient_mu 0.843 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method 'scintillation counter' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4723 _diffrn_reflns_av_R_equivalents 0.0847 _diffrn_reflns_av_sigmaI/netI 0.0871 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 27.78 _reflns_number_total 2486 _reflns_number_observed 2341 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1544P)^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 2486 _refine_ls_number_parameters 160 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_obs 0.0803 _refine_ls_wR_factor_all 0.2157 _refine_ls_wR_factor_obs 0.2134 _refine_ls_goodness_of_fit_all 1.094 _refine_ls_goodness_of_fit_obs 1.115 _refine_ls_restrained_S_all 1.107 _refine_ls_restrained_S_obs 1.129 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N3 N -0.1972(6) 0.1718(5) -0.0442(4) 0.0755(10) Uani 1 d . . O1 O -0.1842(16) 0.3148(13) 0.0220(9) 0.124(3) Uani 0.60 d P . O2 O -0.3225(12) 0.1455(13) -0.1399(8) 0.104(2) Uani 0.60 d P . O1A O -0.2124(14) 0.2502(13) -0.1362(10) 0.083(2) Uani 0.40 d P . O2A O -0.3088(20) 0.1859(20) 0.0273(14) 0.114(4) Uani 0.40 d P . Ni Ni 0.0000 0.0000 0.0000 0.0559(3) Uani 1 d S . N1 N 0.1852(8) 0.2097(6) 0.1256(5) 0.102(2) Uani 1 d . . H1 H 0.2450(8) 0.1460(6) 0.1829(5) 0.122 Uiso 1 calc R 1 N2 N 0.1400(7) 0.1244(7) -0.1303(5) 0.0905(13) Uani 1 d . . H2 H 0.2338(7) 0.0617(7) -0.1272(5) 0.109 Uiso 1 calc R 1 C1 C 0.3333(10) 0.2818(10) 0.0623(9) 0.139(4) Uani 1 d . . H1A H 0.4047(10) 0.3971(10) 0.1052(9) 0.167 Uiso 1 calc R . H1B H 0.4175(10) 0.1979(10) 0.0617(9) 0.167 Uiso 1 calc R . C2 C 0.2461(7) 0.3058(7) -0.0637(4) 0.136(4) Uani 1 d . . H2A H 0.3408(7) 0.3571(7) -0.1068(4) 0.163 Uiso 1 calc R . H2B H 0.1613(7) 0.3891(7) -0.0627(4) 0.163 Uiso 1 calc R . C3 C 0.1020(7) 0.3189(7) 0.1999(4) 0.158(10) Uani 0.50 d PRD 1 H3A H -0.0162(7) 0.2490(7) 0.2087(4) 0.190 Uiso 0.50 calc PR 1 H3B H 0.0768(7) 0.4238(7) 0.1576(4) 0.190 Uiso 0.50 calc PR 1 C4 C 0.2376(7) 0.3888(7) 0.3399(4) 0.216(19) Uani 0.50 d PRD 1 H4A H 0.2517(7) 0.2886(7) 0.3899(4) 0.260 Uiso 0.50 calc PR 1 H4B H 0.3598(7) 0.4548(7) 0.3352(4) 0.260 Uiso 0.50 calc PR 1 C5 C 0.1457(7) 0.4881(7) 0.3791(4) 0.382(41) Uani 0.50 d PRD 1 H5A H 0.2084(7) 0.5400(7) 0.4617(4) 0.458 Uiso 0.50 calc PR 1 H5B H 0.0248(7) 0.4190(7) 0.3802(4) 0.458 Uiso 0.50 calc PR 1 H5C H 0.1317(7) 0.5834(7) 0.3261(4) 0.458 Uiso 0.50 calc PR 1 C6 C 0.0335(7) 0.0832(7) -0.2801(4) 0.187(13) Uani 0.50 d PRD 1 H6A H -0.0345(7) 0.1767(7) -0.3080(4) 0.225 Uiso 0.50 calc PR 1 H6B H -0.0497(7) -0.0347(7) -0.2988(4) 0.225 Uiso 0.50 calc PR 1 C7 C 0.2248(7) 0.0895(7) -0.3401(4) 0.216(19) Uani 0.50 d PRD 1 H7A H 0.2130(7) 0.1809(7) -0.3978(4) 0.260 Uiso 0.50 calc PR 1 H7B H 0.3255(7) 0.1472(7) -0.2711(4) 0.260 Uiso 0.50 calc PR 1 C8 C 0.3081(7) -0.0341(7) -0.4001(4) 0.171(11) Uani 0.50 d PR 1 H8A H 0.4205(7) 0.0299(7) -0.4192(4) 0.206 Uiso 0.50 calc PR 1 H8B H 0.2228(7) -0.0909(7) -0.4755(4) 0.206 Uiso 0.50 calc PR 1 H8C H 0.3375(7) -0.1252(7) -0.3464(4) 0.206 Uiso 0.50 calc PR 1 C3A C 0.2701(7) 0.1915(7) 0.2399(4) 0.184(13) Uani 0.50 d PRD 2 H3A1 H 0.3754(7) 0.1332(7) 0.2387(4) 0.221 Uiso 0.50 calc PR 2 H3A2 H 0.1846(7) 0.1171(7) 0.2802(4) 0.221 Uiso 0.50 calc PR 2 C4A C 0.3466(7) 0.4076(7) 0.3199(4) 0.132(7) Uani 0.50 d PRD 2 H4A1 H 0.4469(7) 0.3909(7) 0.3868(4) 0.159 Uiso 0.50 calc PR 2 H4A2 H 0.4082(7) 0.4760(7) 0.2634(4) 0.159 Uiso 0.50 calc PR 2 C5A C 0.2599(7) 0.5454(7) 0.3791(4) 0.262(23) Uani 0.50 d PR 2 H5A1 H 0.3544(7) 0.6504(7) 0.4145(4) 0.315 Uiso 0.50 calc PR 2 H5A2 H 0.2047(7) 0.4936(7) 0.4431(4) 0.315 Uiso 0.50 calc PR 2 H5A3 H 0.1654(7) 0.5802(7) 0.3174(4) 0.315 Uiso 0.50 calc PR 2 C6A C 0.2290(7) 0.0221(7) -0.2001(4) 0.132(7) Uani 0.50 d PRD 2 H6A1 H 0.1508(7) -0.0955(7) -0.2326(4) 0.158 Uiso 0.50 calc PR 2 H6A2 H 0.3474(7) 0.0049(7) -0.1514(4) 0.158 Uiso 0.50 calc PR 2 C7A C 0.2616(7) 0.1594(7) -0.3201(4) 0.230(19) Uani 0.50 d PRD 2 H7A1 H 0.1421(7) 0.1583(7) -0.3753(4) 0.276 Uiso 0.50 calc PR 2 H7A2 H 0.3155(7) 0.2835(7) -0.2852(4) 0.276 Uiso 0.50 calc PR 2 C8A C 0.3696(7) 0.1004(7) -0.3809(4) 0.341(32) Uani 0.50 d PRD 2 H8A1 H 0.3867(7) 0.1759(7) -0.4461(4) 0.409 Uiso 0.50 calc PR 2 H8A2 H 0.3152(7) -0.0219(7) -0.4162(4) 0.409 Uiso 0.50 calc PR 2 H8A3 H 0.4883(7) 0.1030(7) -0.3263(4) 0.409 Uiso 0.50 calc PR 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 N3 0.064(2) 0.058(2) 0.108(3) 0.015(2) 0.023(2) 0.017(2) O1 0.132(7) 0.095(5) 0.147(7) -0.018(5) 0.009(6) 0.064(6) O2 0.091(5) 0.107(6) 0.113(5) 0.012(4) 0.001(4) 0.038(5) O1A 0.072(5) 0.071(5) 0.114(6) 0.035(5) 0.021(5) 0.024(4) O2A 0.110(9) 0.116(9) 0.165(11) 0.058(8) 0.085(9) 0.072(8) Ni 0.0483(4) 0.0402(4) 0.0812(5) 0.0095(3) 0.0204(3) 0.0060(2) N1 0.104(4) 0.056(2) 0.117(3) -0.001(2) -0.019(3) -0.002(2) N2 0.072(2) 0.101(3) 0.115(3) 0.051(3) 0.043(2) 0.024(2) C1 0.082(4) 0.086(4) 0.207(9) 0.051(5) -0.023(5) -0.041(4) C2 0.083(4) 0.104(5) 0.223(9) 0.092(6) 0.040(5) -0.009(4) C3 0.288(28) 0.098(10) 0.087(7) -0.015(6) -0.015(11) 0.106(15) C4 0.248(34) 0.198(25) 0.143(17) -0.077(18) 0.085(20) -0.125(26) C5 0.477(90) 0.493(99) 0.163(39) 0.071(54) 0.070(48) 0.058(89) C6 0.125(14) 0.295(29) 0.209(20) 0.194(23) 0.093(15) 0.094(17) C7 0.235(38) 0.247(34) 0.190(26) -0.014(25) 0.159(28) -0.008(30) C8 0.183(25) 0.224(30) 0.100(12) 0.003(15) 0.029(13) 0.030(22) C3A 0.189(20) 0.089(10) 0.196(18) -0.002(11) -0.113(17) 0.009(11) C4A 0.130(13) 0.121(12) 0.100(9) -0.003(8) -0.014(9) -0.045(11) C5A 0.371(56) 0.248(41) 0.238(40) 0.092(34) 0.074(38) 0.215(41) C6A 0.124(12) 0.221(20) 0.092(7) 0.051(10) 0.048(7) 0.104(14) C7A 0.289(49) 0.287(40) 0.117(16) 0.085(21) 0.073(22) 0.014(35) C8A 0.317(55) 0.537(78) 0.174(31) -0.122(45) -0.030(33) 0.248(54) _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 N3 O1A 1.203(10) . ? N3 O2 1.238(9) . ? N3 O1 1.243(9) . ? N3 O2A 1.277(11) . ? N3 Ni 2.134(4) . ? O1 O2A 1.23(2) . ? O1 O1A 1.749(14) . ? O2 O1A 1.023(13) . ? Ni N1 2.118(4) . ? Ni N1 2.118(4) 2 ? Ni N2 2.119(4) . ? Ni N2 2.119(4) 2 ? Ni N3 2.134(4) 2 ? N1 C3A 1.319(7) . ? N1 C3 1.434(9) . ? N1 C1 1.471(11) . ? N2 C6A 1.402(8) . ? N2 C2 1.510(8) . ? N2 C6 1.668(7) . ? C1 C2 1.448(10) . ? C3 C4 1.66 . ? C4 C5 1.22 . ? C6 C7 1.69 . ? C7 C8 1.42 . ? C3A C4A 1.74 . ? C4A C5A 1.51 . ? C6A C7A 1.76 . ? C7A C8A 1.27 . ? 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 O1A N3 O2 49.5(6) . . ? O1A N3 O1 91.3(8) . . ? O2 N3 O1 115.1(6) . . ? O1A N3 O2A 118.7(8) . . ? O2 N3 O2A 93.8(9) . . ? O1 N3 O2A 58.4(8) . . ? O1A N3 Ni 122.7(6) . . ? O2 N3 Ni 123.6(5) . . ? O1 N3 Ni 121.0(5) . . ? O2A N3 Ni 118.6(6) . . ? O2A O1 N3 62.2(7) . . ? O2A O1 O1A 89.7(9) . . ? N3 O1 O1A 43.4(5) . . ? O1A O2 N3 63.5(7) . . ? O2 O1A N3 67.0(7) . . ? O2 O1A O1 94.5(10) . . ? N3 O1A O1 45.3(5) . . ? O1 O2A N3 59.4(7) . . ? N1 Ni N1 180.0 . 2 ? N1 Ni N2 82.9(2) . . ? N1 Ni N2 97.1(2) 2 . ? N1 Ni N2 97.1(2) . 2 ? N1 Ni N2 82.9(2) 2 2 ? N2 Ni N2 180.0 . 2 ? N1 Ni N3 89.1(2) . 2 ? N1 Ni N3 90.9(2) 2 2 ? N2 Ni N3 92.3(2) . 2 ? N2 Ni N3 87.7(2) 2 2 ? N1 Ni N3 90.9(2) . . ? N1 Ni N3 89.1(2) 2 . ? N2 Ni N3 87.7(2) . . ? N2 Ni N3 92.3(2) 2 . ? N3 Ni N3 180.0 2 . ? C3A N1 C1 106.2(5) . . ? C3 N1 C1 124.5(5) . . ? C3A N1 Ni 125.4(4) . . ? C3 N1 Ni 116.4(4) . . ? C1 N1 Ni 106.0(5) . . ? C6A N2 C2 119.0(5) . . ? C2 N2 C6 126.3(4) . . ? C6A N2 Ni 119.6(3) . . ? C2 N2 Ni 104.6(3) . . ? C6 N2 Ni 117.9(3) . . ? C2 C1 N1 108.2(5) . . ? C1 C2 N2 109.4(4) . . ? N1 C3 C4 112.5(3) . . ? C5 C4 C3 99.8 . . ? N2 C6 C7 98.5(2) . . ? C8 C7 C6 137.7 . . ? N1 C3A C4A 107.8(3) . . ? C5A C4A C3A 136.6 . . ? N2 C6A C7A 102.0(2) . . ? C8A C7A C6A 109.9 . . ? _refine_diff_density_max 0.960 _refine_diff_density_min -0.795 _refine_diff_density_rms 0.095 data_1a _database_code_CSD 153399 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H40 N6 Ni O4' _chemical_formula_weight 439.25 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2830(9) _cell_length_b 19.467(2) _cell_length_c 12.124(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.400(10) _cell_angle_gamma 90.00 _cell_volume 2416.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method 'scintillation counter' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4466 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4219 _reflns_number_observed 2557 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 fullcycle _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+2.1742P] 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 4217 _refine_ls_number_parameters 298 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_obs 0.0521 _refine_ls_wR_factor_all 0.1372 _refine_ls_wR_factor_obs 0.1086 _refine_ls_goodness_of_fit_all 1.006 _refine_ls_goodness_of_fit_obs 1.048 _refine_ls_restrained_S_all 1.017 _refine_ls_restrained_S_obs 1.061 _refine_ls_shift/esd_max 0.007 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N6 N 0.2235(8) 0.1751(6) 0.6040(6) 0.158(5) Uani 1 d D . O3 O 0.2470(6) 0.2252(3) 0.6567(5) 0.111(2) Uani 1 d D . O4 O 0.1932(7) 0.1861(3) 0.5193(8) 0.180(3) Uani 1 d D . Ni Ni 0.24548(5) 0.09738(3) 0.94152(5) 0.0483(2) Uani 1 d . . O2 O 0.1640(3) 0.0127(2) 1.0223(3) 0.0669(9) Uani 1 d . . O1 O 0.3443(3) 0.0015(2) 0.9596(3) 0.0655(9) Uani 1 d . . N5 N 0.2576(5) -0.0269(2) 1.0106(4) 0.0710(12) Uani 1 d . . N1 N 0.1428(4) 0.0696(2) 0.7871(3) 0.0627(11) Uani 1 d . . H1 H 0.1819(4) 0.0923(2) 0.7335(3) 0.075 Uiso 1 calc R 1 N2 N 0.0943(4) 0.1695(2) 0.9474(3) 0.0590(10) Uani 1 d . . H2 H 0.1312(4) 0.2115(2) 0.9613(3) 0.071 Uiso 1 calc R . N3 N 0.3474(4) 0.1350(2) 1.0900(3) 0.0575(10) Uani 1 d . . H3 H 0.3018(4) 0.1716(2) 1.1126(3) 0.069 Uiso 1 calc R 1 N4 N 0.3822(3) 0.1562(2) 0.8644(3) 0.0573(10) Uani 1 d . . H4 H 0.3380(3) 0.1831(2) 0.8122(3) 0.069 Uiso 1 calc R . C1 C 0.0127(5) 0.0996(4) 0.7896(4) 0.080(2) Uani 1 d . . H1A H -0.0390(5) 0.0715(4) 0.8352(4) 0.097 Uiso 1 calc R . H1B H -0.0312(5) 0.1010(4) 0.7153(4) 0.097 Uiso 1 calc R . C2 C 0.0254(5) 0.1710(3) 0.8363(5) 0.080(2) Uani 1 d . . H2A H 0.0731(5) 0.1996(3) 0.7883(5) 0.096 Uiso 1 calc R . H2B H -0.0607(5) 0.1908(3) 0.8395(5) 0.096 Uiso 1 calc R . C3 C 0.4721(5) 0.1613(3) 1.0566(5) 0.072(2) Uani 1 d . . H3A H 0.5306(5) 0.1233(3) 1.0455(5) 0.086 Uiso 1 calc R . H3B H 0.5134(5) 0.1907(3) 1.1142(5) 0.086 Uiso 1 calc R . C4 C 0.4461(5) 0.2013(3) 0.9507(5) 0.073(2) Uani 1 d . . H4A H 0.3902(5) 0.2402(3) 0.9625(5) 0.087 Uiso 1 calc R . H4B H 0.5277(5) 0.2186(3) 0.9274(5) 0.087 Uiso 1 calc R . C8 C 0.0090(5) 0.1547(3) 1.0349(4) 0.0678(14) Uani 1 d . . H8A H 0.0624(5) 0.1495(3) 1.1047(4) 0.081 Uiso 1 calc R . H8B H -0.0350(5) 0.1113(3) 1.0186(4) 0.081 Uiso 1 calc R . C9 C -0.0950(6) 0.2108(4) 1.0481(6) 0.117(3) Uani 1 d . . H9A H -0.0523(6) 0.2552(4) 1.0571(6) 0.140 Uiso 1 calc R . H9B H -0.1551(6) 0.2126(4) 0.9815(6) 0.140 Uiso 1 calc R . C10 C -0.1672(7) 0.1977(4) 1.1422(8) 0.149(3) Uani 1 d . . H10A H -0.2306(7) 0.2334(4) 1.1479(8) 0.179 Uiso 1 calc R . H10B H -0.1082(7) 0.1968(4) 1.2084(8) 0.179 Uiso 1 calc R . H10C H -0.2108(7) 0.1542(4) 1.1329(8) 0.179 Uiso 1 calc R . C14 C 0.4744(5) 0.1131(2) 0.8091(4) 0.0623(13) Uani 1 d . . H14A H 0.4248(5) 0.0810(2) 0.7604(4) 0.075 Uiso 1 calc R . H14B H 0.5258(5) 0.0864(2) 0.8650(4) 0.075 Uiso 1 calc R . C15 C 0.5676(6) 0.1527(3) 0.7412(6) 0.098(2) Uani 1 d . . H15A H 0.5170(6) 0.1806(3) 0.6866(6) 0.118 Uiso 1 calc R . H15B H 0.6207(6) 0.1833(3) 0.7899(6) 0.118 Uiso 1 calc R . C16 C 0.6539(6) 0.1070(4) 0.6843(6) 0.110(2) Uani 1 d . . H16A H 0.7104(6) 0.1341(4) 0.6429(6) 0.133 Uiso 1 calc R . H16B H 0.6020(6) 0.0772(4) 0.6347(6) 0.133 Uiso 1 calc R . H16C H 0.7056(6) 0.0799(4) 0.7381(6) 0.133 Uiso 1 calc R . C5 C 0.1272(10) -0.0078(4) 0.7479(9) 0.092(3) Uani 0.60 d P 1 H5A H 0.2114(10) -0.0303(4) 0.7609(9) 0.110 Uiso 0.60 calc PR 1 H5B H 0.0678(10) -0.0307(4) 0.7937(9) 0.110 Uiso 0.60 calc PR 1 C6 C 0.0812(13) -0.0168(6) 0.6378(8) 0.115(4) Uani 0.60 d P 1 H6A H 0.1274(13) 0.0142(6) 0.5925(8) 0.138 Uiso 0.60 calc PR 1 H6B H -0.0107(13) -0.0049(6) 0.6281(8) 0.138 Uiso 0.60 calc PR 1 C7 C 0.0977(22) -0.0874(7) 0.5994(14) 0.227(11) Uani 0.60 d P 1 H7A H 0.0645(22) -0.0910(7) 0.5230(14) 0.273 Uiso 0.60 calc PR 1 H7B H 0.0506(22) -0.1183(7) 0.6429(14) 0.273 Uiso 0.60 calc PR 1 H7C H 0.1888(22) -0.0992(7) 0.6073(14) 0.273 Uiso 0.60 calc PR 1 C11 C 0.3686(9) 0.0877(5) 1.1850(7) 0.075(3) Uani 0.60 d P 1 H11A H 0.4228(9) 0.0495(5) 1.1662(7) 0.090 Uiso 0.60 calc PR 1 H11B H 0.2856(9) 0.0696(5) 1.2038(7) 0.090 Uiso 0.60 calc PR 1 C12 C 0.4383(12) 0.1285(6) 1.2874(8) 0.101(4) Uani 0.60 d P 1 H12A H 0.5261(12) 0.1413(6) 1.2723(8) 0.121 Uiso 0.60 calc PR 1 H12B H 0.3901(12) 0.1702(6) 1.2998(8) 0.121 Uiso 0.60 calc PR 1 C13 C 0.4436(21) 0.0842(9) 1.3874(12) 0.238(11) Uani 0.60 d P 1 H13A H 0.4857(21) 0.1086(9) 1.4497(12) 0.285 Uiso 0.60 calc PR 1 H13B H 0.4921(21) 0.0432(9) 1.3749(12) 0.285 Uiso 0.60 calc PR 1 H13C H 0.3565(21) 0.0721(9) 1.4023(12) 0.285 Uiso 0.60 calc PR 1 C5A C 0.1579(15) 0.0053(6) 0.7515(10) 0.080(5) Uani 0.40 d PD 2 H5C H 0.0827(15) -0.0207(6) 0.7707(10) 0.096 Uiso 0.40 calc PR 2 H5D H 0.2335(15) -0.0136(6) 0.7951(10) 0.096 Uiso 0.40 calc PR 2 C6A C 0.1740(49) -0.0096(13) 0.6355(25) 0.376(35) Uani 0.40 d PD 2 H6C H 0.1024(49) 0.0124(13) 0.5912(25) 0.451 Uiso 0.40 calc PR 2 H6D H 0.2536(49) 0.0129(13) 0.6179(25) 0.451 Uiso 0.40 calc PR 2 C7A C 0.1799(34) -0.0802(17) 0.5977(22) 0.327(26) Uani 0.40 d PD 2 H7D H 0.1906(34) -0.0808(17) 0.5199(22) 0.392 Uiso 0.40 calc PR 2 H7E H 0.1005(34) -0.1034(17) 0.6107(22) 0.392 Uiso 0.40 calc PR 2 H7F H 0.2526(34) -0.1030(17) 0.6376(22) 0.392 Uiso 0.40 calc PR 2 C11A C 0.3590(18) 0.0962(6) 1.1988(11) 0.093(5) Uani 0.40 d P 2 H11C H 0.2808(18) 0.0682(6) 1.1983(11) 0.111 Uiso 0.40 calc PR 2 H11D H 0.4313(18) 0.0645(6) 1.1954(11) 0.111 Uiso 0.40 calc PR 2 C12A C 0.3763(16) 0.1272(8) 1.3050(12) 0.092(5) Uani 0.40 d P 2 H12C H 0.2986(16) 0.1536(8) 1.3161(12) 0.110 Uiso 0.40 calc PR 2 H12D H 0.4488(16) 0.1592(8) 1.3061(12) 0.110 Uiso 0.40 calc PR 2 C13A C 0.4012(28) 0.0801(10) 1.3971(13) 0.186(13) Uani 0.40 d P 2 H13D H 0.4116(28) 0.1055(10) 1.4652(13) 0.223 Uiso 0.40 calc PR 2 H13E H 0.4795(28) 0.0546(10) 1.3886(13) 0.223 Uiso 0.40 calc PR 2 H13F H 0.3290(28) 0.0490(10) 1.3986(13) 0.223 Uiso 0.40 calc PR 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 N6 0.083(5) 0.322(16) 0.071(5) 0.071(7) 0.008(4) 0.037(8) O3 0.097(4) 0.111(4) 0.124(5) 0.057(3) 0.010(4) 0.004(3) O4 0.158(6) 0.122(5) 0.265(9) 0.025(6) 0.047(7) 0.013(4) Ni 0.0416(3) 0.0423(3) 0.0600(4) 0.0032(3) -0.0008(2) -0.0001(3) O2 0.060(2) 0.061(2) 0.079(2) 0.013(2) 0.004(2) -0.004(2) O1 0.055(2) 0.054(2) 0.086(3) -0.003(2) -0.002(2) 0.007(2) N5 0.077(3) 0.045(2) 0.087(3) 0.006(2) -0.012(3) -0.003(2) N1 0.059(3) 0.068(3) 0.060(3) 0.003(2) -0.003(2) -0.010(2) N2 0.049(2) 0.050(2) 0.077(3) 0.008(2) 0.004(2) 0.004(2) N3 0.057(2) 0.049(2) 0.064(3) -0.005(2) -0.007(2) 0.008(2) N4 0.047(2) 0.047(2) 0.078(3) 0.009(2) 0.006(2) 0.002(2) C1 0.055(3) 0.117(5) 0.066(3) 0.007(4) -0.011(3) -0.004(4) C2 0.062(3) 0.099(5) 0.079(4) 0.024(4) 0.001(3) 0.026(3) C3 0.056(3) 0.064(3) 0.092(4) -0.025(3) -0.012(3) 0.002(3) C4 0.062(3) 0.049(3) 0.110(5) -0.010(3) 0.015(3) -0.011(3) C8 0.055(3) 0.067(3) 0.082(4) -0.004(3) 0.013(3) 0.005(3) C9 0.078(4) 0.148(7) 0.132(6) 0.005(5) 0.044(4) 0.026(5) C10 0.094(5) 0.130(7) 0.228(10) -0.060(7) 0.036(6) -0.001(5) C14 0.052(3) 0.059(3) 0.076(3) 0.005(3) 0.005(2) -0.004(2) C15 0.077(4) 0.093(5) 0.130(6) 0.012(4) 0.040(4) -0.006(4) C16 0.083(4) 0.133(6) 0.120(6) 0.005(5) 0.033(4) -0.001(4) C5 0.093(7) 0.056(6) 0.122(9) -0.038(6) -0.011(6) -0.042(5) C6 0.168(12) 0.089(8) 0.075(7) -0.020(6) -0.055(7) -0.020(8) C7 0.371(30) 0.103(12) 0.181(16) -0.040(11) -0.112(18) -0.024(15) C11 0.079(6) 0.085(7) 0.057(5) -0.011(5) -0.018(4) 0.008(5) C12 0.138(10) 0.089(7) 0.070(7) -0.006(6) -0.026(7) 0.006(7) C13 0.360(28) 0.186(17) 0.133(13) -0.022(13) -0.157(16) -0.021(18) C5A 0.132(12) 0.052(8) 0.047(7) 0.000(6) -0.040(7) -0.059(8) C6A 0.686(92) 0.134(24) 0.355(51) -0.162(31) 0.305(58) -0.127(39) C7A 0.296(41) 0.532(70) 0.159(26) -0.236(37) 0.054(26) -0.017(44) C11A 0.167(16) 0.030(6) 0.078(10) -0.006(7) -0.007(9) 0.023(9) C12A 0.105(12) 0.095(11) 0.076(10) -0.029(9) 0.007(9) 0.006(10) C13A 0.387(39) 0.126(17) 0.050(10) 0.026(10) 0.045(16) 0.136(21) _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 N6 O4 1.066(9) . ? N6 O3 1.178(11) . ? Ni N4 2.100(4) . ? Ni N2 2.101(4) . ? Ni O1 2.126(3) . ? Ni N3 2.126(4) . ? Ni O2 2.129(3) . ? Ni N1 2.131(4) . ? O2 N5 1.252(5) . ? O1 N5 1.260(5) . ? N1 C5A 1.338(13) . ? N1 C1 1.462(6) . ? N1 C5 1.584(9) . ? N2 C2 1.462(6) . ? N2 C8 1.468(6) . ? N3 C3 1.472(6) . ? N3 C11 1.474(9) . ? N3 C11A 1.515(13) . ? N4 C4 1.472(6) . ? N4 C14 1.475(6) . ? C1 C2 1.503(8) . ? C3 C4 1.504(7) . ? C8 C9 1.548(8) . ? C9 C10 1.441(9) . ? C14 C15 1.528(7) . ? C15 C16 1.473(8) . ? C5 C6 1.385(12) . ? C6 C7 1.47(2) . ? C11 C12 1.588(12) . ? C12 C13 1.49(2) . ? C5A C6A 1.46(2) . ? C6A C7A 1.45(2) . ? C11A C12A 1.42(2) . ? C12A C13A 1.45(2) . ? 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 O4 N6 O3 112.5(13) . . ? N4 Ni N2 100.31(15) . . ? N4 Ni O1 101.03(14) . . ? N2 Ni O1 158.59(15) . . ? N4 Ni N3 83.8(2) . . ? N2 Ni N3 92.80(15) . . ? O1 Ni N3 91.27(14) . . ? N4 Ni O2 159.41(14) . . ? N2 Ni O2 100.21(15) . . ? O1 Ni O2 58.54(13) . . ? N3 Ni O2 93.50(14) . . ? N4 Ni N1 92.5(2) . . ? N2 Ni N1 83.8(2) . . ? O1 Ni N1 93.47(15) . . ? N3 Ni N1 174.5(2) . . ? O2 Ni N1 91.38(15) . . ? N5 O2 Ni 94.9(3) . . ? N5 O1 Ni 94.8(3) . . ? O2 N5 O1 111.8(4) . . ? C5A N1 C1 121.0(8) . . ? C1 N1 C5 108.6(5) . . ? C5A N1 Ni 117.2(6) . . ? C1 N1 Ni 105.0(3) . . ? C5 N1 Ni 122.1(4) . . ? C2 N2 C8 113.6(4) . . ? C2 N2 Ni 106.1(3) . . ? C8 N2 Ni 112.8(3) . . ? C3 N3 C11 111.4(5) . . ? C3 N3 C11A 114.5(8) . . ? C3 N3 Ni 105.0(3) . . ? C11 N3 Ni 118.1(4) . . ? C11A N3 Ni 123.9(6) . . ? C4 N4 C14 113.6(4) . . ? C4 N4 Ni 106.3(3) . . ? C14 N4 Ni 112.2(3) . . ? N1 C1 C2 109.3(4) . . ? N2 C2 C1 110.2(4) . . ? N3 C3 C4 109.0(4) . . ? N4 C4 C3 109.2(4) . . ? N2 C8 C9 113.6(5) . . ? C10 C9 C8 111.6(6) . . ? N4 C14 C15 114.9(4) . . ? C16 C15 C14 112.6(5) . . ? C6 C5 N1 115.1(9) . . ? C5 C6 C7 112.7(11) . . ? N3 C11 C12 108.7(7) . . ? C13 C12 C11 109.1(10) . . ? N1 C5A C6A 121.5(14) . . ? C7A C6A C5A 120.3(24) . . ? C12A C11A N3 124.8(11) . . ? C11A C12A C13A 115.3(14) . . ? _refine_diff_density_max 0.355 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.054 data_1b _database_code_CSD 153400 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H40 N6 Ni O4' _chemical_formula_weight 439.25 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.3131(7) _cell_length_b 19.2548(12) _cell_length_c 12.0523(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.470(10) _cell_angle_gamma 90.00 _cell_volume 2378.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.845 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method 'scintillation counter' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6836 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3995 _reflns_number_observed 3823 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+2.1492P] 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 3995 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_obs 0.0404 _refine_ls_wR_factor_all 0.1095 _refine_ls_wR_factor_obs 0.1069 _refine_ls_goodness_of_fit_all 1.050 _refine_ls_goodness_of_fit_obs 1.049 _refine_ls_restrained_S_all 1.050 _refine_ls_restrained_S_obs 1.049 _refine_ls_shift/esd_max -0.009 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ni Ni 0.25427(3) 0.097063(14) 0.05852(2) 0.03195(13) Uani 1 d . . N5 N 0.2411(2) -0.02895(11) -0.0100(2) 0.0480(5) Uani 1 d . . O1 O 0.1536(2) 0.00025(9) 0.0382(2) 0.0452(4) Uani 1 d . . O2 O 0.3361(2) 0.01113(9) -0.0200(2) 0.0454(4) Uani 1 d . . N1 N 0.3540(2) 0.06849(12) 0.2166(2) 0.0429(5) Uani 1 d . . H1 H 0.3169(2) 0.09391(12) 0.2683(2) 0.052 Uiso 1 calc R . N2 N 0.4064(2) 0.16968(11) 0.0560(2) 0.0404(5) Uani 1 d . . H2 H 0.3705(2) 0.21251(11) 0.0434(2) 0.049 Uiso 1 calc R . N3 N 0.1541(2) 0.13507(10) -0.0932(2) 0.0399(5) Uani 1 d . . H3 H 0.1994(2) 0.17312(10) -0.1117(2) 0.048 Uiso 1 calc R . N4 N 0.1181(2) 0.15803(10) 0.1332(2) 0.0390(5) Uani 1 d . . H4 H 0.1624(2) 0.18587(10) 0.1854(2) 0.047 Uiso 1 calc R . C1 C 0.4863(3) 0.0963(2) 0.2150(3) 0.0551(8) Uani 1 d . . H1A H 0.5349(3) 0.0673(2) 0.1685(3) 0.066 Uiso 1 calc R . H1B H 0.5316(3) 0.0964(2) 0.2900(3) 0.066 Uiso 1 calc R . C2 C 0.4779(3) 0.1689(2) 0.1696(2) 0.0540(7) Uani 1 d . . H2A H 0.4332(3) 0.1984(2) 0.2185(2) 0.065 Uiso 1 calc R . H2B H 0.5651(3) 0.1873(2) 0.1672(2) 0.065 Uiso 1 calc R . C3 C 0.0290(3) 0.16122(14) -0.0629(2) 0.0470(6) Uani 1 d . . H3A H -0.0288(3) 0.12259(14) -0.0524(2) 0.056 Uiso 1 calc R . H3B H -0.0124(3) 0.19033(14) -0.1223(2) 0.056 Uiso 1 calc R . C4 C 0.0528(3) 0.20252(13) 0.0433(3) 0.0475(7) Uani 1 d . . H4A H 0.1072(3) 0.24235(13) 0.0318(3) 0.057 Uiso 1 calc R . H4B H -0.0296(3) 0.21931(13) 0.0646(3) 0.057 Uiso 1 calc R . C5 C 0.3526(4) -0.0049(2) 0.2554(3) 0.0664(9) Uani 1 d . . H5A H 0.2646(4) -0.0227(2) 0.2385(3) 0.080 Uiso 1 calc R . H5B H 0.4086(4) -0.0318(2) 0.2123(3) 0.080 Uiso 1 calc R . C6 C 0.3941(8) -0.0170(3) 0.3740(4) 0.133(2) Uani 1 d . . H6A H 0.3523(8) 0.0168(3) 0.4179(4) 0.159 Uiso 1 calc R . H6B H 0.4877(8) -0.0101(3) 0.3883(4) 0.159 Uiso 1 calc R . C7 C 0.3602(11) -0.0910(3) 0.4118(5) 0.179(4) Uani 1 d . . H7A H 0.3892(11) -0.0964(3) 0.4899(5) 0.268 Uiso 1 calc R . H7B H 0.4028(11) -0.1246(3) 0.3697(5) 0.268 Uiso 1 calc R . H7C H 0.2675(11) -0.0977(3) 0.3994(5) 0.268 Uiso 1 calc R . C8 C 0.4912(3) 0.15508(14) -0.0327(2) 0.0436(6) Uani 1 d . . H8A H 0.4367(3) 0.14933(14) -0.1031(2) 0.052 Uiso 1 calc R . H8B H 0.5366(3) 0.11156(14) -0.0158(2) 0.052 Uiso 1 calc R . C9 C 0.5923(3) 0.2120(2) -0.0463(3) 0.0675(9) Uani 1 d . . H9A H 0.5482(3) 0.2563(2) -0.0583(3) 0.081 Uiso 1 calc R . H9B H 0.6520(3) 0.2154(2) 0.0217(3) 0.081 Uiso 1 calc R . C10 C 0.6684(4) 0.1969(2) -0.1429(4) 0.0766(11) Uani 1 d . . H10A H 0.7307(4) 0.2333(2) -0.1494(4) 0.115 Uiso 1 calc R . H10B H 0.6097(4) 0.1943(2) -0.2105(4) 0.115 Uiso 1 calc R . H10C H 0.7133(4) 0.1534(2) -0.1306(4) 0.115 Uiso 1 calc R . C11 C 0.1389(4) 0.09073(15) -0.1938(2) 0.0544(8) Uani 1 d . . H11A H 0.0779(4) 0.05376(15) -0.1825(2) 0.065 Uiso 1 calc R . H11B H 0.2224(4) 0.06939(15) -0.2025(2) 0.065 Uiso 1 calc R . C12 C 0.0911(5) 0.1286(2) -0.3010(3) 0.0891(14) Uani 1 d . . H12A H 0.0066(5) 0.1491(2) -0.2935(3) 0.107 Uiso 1 calc R . H12B H 0.1512(5) 0.1660(2) -0.3122(3) 0.107 Uiso 1 calc R . C13 C 0.0790(7) 0.0820(2) -0.4025(3) 0.117(2) Uani 1 d . . H13A H 0.0486(7) 0.1087(2) -0.4676(3) 0.153 Uiso 1 calc R . H13B H 0.0181(7) 0.0454(2) -0.3929(3) 0.153 Uiso 1 calc R . H13C H 0.1627(7) 0.0624(2) -0.4116(3) 0.153 Uiso 1 calc R . C14 C 0.0251(3) 0.11486(13) 0.1887(2) 0.0413(6) Uani 1 d . . H14A H 0.0746(3) 0.08259(13) 0.2388(2) 0.050 Uiso 1 calc R . H14B H -0.0267(3) 0.08771(13) 0.1322(2) 0.050 Uiso 1 calc R . C15 C -0.0668(3) 0.1554(2) 0.2548(3) 0.0620(8) Uani 1 d . . H15A H -0.0158(3) 0.1828(2) 0.3116(3) 0.074 Uiso 1 calc R . H15B H -0.1180(3) 0.1872(2) 0.2051(3) 0.074 Uiso 1 calc R . C16 C -0.1572(3) 0.1086(2) 0.3098(3) 0.0647(9) Uani 1 d . . H16A H -0.2134(3) 0.1361(2) 0.3505(3) 0.097 Uiso 1 calc R . H16B H -0.1070(3) 0.0776(2) 0.3602(3) 0.097 Uiso 1 calc R . H16C H -0.2091(3) 0.0821(2) 0.2538(3) 0.097 Uiso 1 calc R . O3 O 0.2559(3) 0.2247(2) 0.3462(3) 0.0736(7) Uani 1 d . . N6 N 0.2792(3) 0.1793(2) 0.3975(3) 0.0746(10) Uani 1 d . . O4 O 0.3134(3) 0.1832(2) 0.4978(3) 0.0999(10) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0280(2) 0.0288(2) 0.0385(2) -0.00200(11) 0.00115(13) -0.00024(10) N5 0.0506(14) 0.0344(11) 0.0561(14) -0.0040(10) -0.0070(11) 0.0026(10) O1 0.0388(10) 0.0369(9) 0.0589(12) 0.0023(8) 0.0009(8) -0.0032(7) O2 0.0413(10) 0.0424(10) 0.0523(11) -0.0057(8) 0.0042(8) 0.0042(8) N1 0.0422(12) 0.0433(12) 0.0428(12) -0.0024(9) 0.0027(9) 0.0038(9) N2 0.0344(11) 0.0364(11) 0.0502(13) -0.0047(9) 0.0031(9) -0.0031(8) N3 0.0403(11) 0.0320(10) 0.0454(12) 0.0019(9) -0.0034(9) -0.0046(8) N4 0.0320(10) 0.0332(10) 0.0516(12) -0.0052(9) 0.0041(9) -0.0028(8) C1 0.0378(15) 0.082(2) 0.043(2) -0.0026(14) -0.0052(12) 0.0067(13) C2 0.0389(14) 0.069(2) 0.053(2) -0.0162(14) 0.0027(12) -0.0173(13) C3 0.0369(13) 0.0434(14) 0.059(2) 0.0142(12) -0.0035(12) -0.0015(11) C4 0.0395(14) 0.0347(13) 0.070(2) 0.0065(12) 0.0118(13) 0.0061(11) C5 0.091(3) 0.048(2) 0.057(2) 0.0073(14) -0.003(2) 0.012(2) C6 0.220(7) 0.083(3) 0.081(3) 0.021(3) -0.043(4) -0.005(4) C7 0.344(13) 0.100(4) 0.088(4) 0.043(3) 0.009(6) 0.005(6) C8 0.0353(13) 0.0432(14) 0.053(2) 0.0002(12) 0.0067(11) -0.0010(11) C9 0.053(2) 0.066(2) 0.086(2) 0.000(2) 0.021(2) -0.014(2) C10 0.060(2) 0.064(2) 0.113(3) 0.023(2) 0.037(2) 0.007(2) C11 0.073(2) 0.042(2) 0.044(2) 0.0006(12) -0.0116(14) -0.0052(13) C12 0.147(4) 0.060(2) 0.052(2) 0.007(2) -0.030(2) -0.005(2) C13 0.209(7) 0.082(3) 0.049(2) 0.002(2) -0.037(3) -0.023(3) C14 0.0355(13) 0.0371(12) 0.052(2) -0.0024(11) 0.0074(11) 0.0000(10) C15 0.057(2) 0.052(2) 0.082(2) -0.007(2) 0.031(2) 0.0012(14) C16 0.055(2) 0.076(2) 0.067(2) -0.006(2) 0.021(2) -0.003(2) O3 0.066(2) 0.075(2) 0.081(2) -0.0376(15) 0.0092(14) 0.0001(13) N6 0.053(2) 0.125(3) 0.047(2) -0.029(2) 0.0110(14) -0.017(2) O4 0.101(2) 0.077(2) 0.123(3) -0.002(2) 0.021(2) -0.003(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 Ni N2 2.105(2) . ? Ni N4 2.108(2) . ? Ni N3 2.126(2) . ? Ni O2 2.127(2) . ? Ni N1 2.133(2) . ? Ni O1 2.134(2) . ? N5 O1 1.260(3) . ? N5 O2 1.264(3) . ? N1 C1 1.468(4) . ? N1 C5 1.489(4) . ? N2 C2 1.481(4) . ? N2 C8 1.482(3) . ? N3 C3 1.470(3) . ? N3 C11 1.477(4) . ? N4 C4 1.482(4) . ? N4 C14 1.484(3) . ? C1 C2 1.501(4) . ? C3 C4 1.503(4) . ? C5 C6 1.464(6) . ? C6 C7 1.547(7) . ? C8 C9 1.535(4) . ? C9 C10 1.504(5) . ? C11 C12 1.517(4) . ? C12 C13 1.510(5) . ? C14 C15 1.521(4) . ? C15 C16 1.504(4) . ? O3 N6 1.082(4) . ? N6 O4 1.222(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni N4 99.78(8) . . ? N2 Ni N3 92.84(8) . . ? N4 Ni N3 83.87(8) . . ? N2 Ni O2 100.15(8) . . ? N4 Ni O2 160.01(8) . . ? N3 Ni O2 93.66(8) . . ? N2 Ni N1 84.21(9) . . ? N4 Ni N1 92.28(9) . . ? N3 Ni N1 174.70(8) . . ? O2 Ni N1 91.20(8) . . ? N2 Ni O1 158.82(8) . . ? N4 Ni O1 101.34(8) . . ? N3 Ni O1 91.10(8) . . ? O2 Ni O1 58.80(7) . . ? N1 Ni O1 93.24(8) . . ? O1 N5 O2 112.0(2) . . ? N5 O1 Ni 94.50(14) . . ? N5 O2 Ni 94.69(14) . . ? C1 N1 C5 113.1(2) . . ? C1 N1 Ni 104.4(2) . . ? C5 N1 Ni 120.3(2) . . ? C2 N2 C8 113.1(2) . . ? C2 N2 Ni 105.9(2) . . ? C8 N2 Ni 112.7(2) . . ? C3 N3 C11 112.8(2) . . ? C3 N3 Ni 105.0(2) . . ? C11 N3 Ni 120.2(2) . . ? C4 N4 C14 112.9(2) . . ? C4 N4 Ni 106.3(2) . . ? C14 N4 Ni 112.07(15) . . ? N1 C1 C2 109.2(2) . . ? N2 C2 C1 110.4(2) . . ? N3 C3 C4 109.2(2) . . ? N4 C4 C3 109.5(2) . . ? C6 C5 N1 116.5(3) . . ? C5 C6 C7 112.5(5) . . ? N2 C8 C9 113.9(2) . . ? C10 C9 C8 111.4(3) . . ? N3 C11 C12 114.6(3) . . ? C13 C12 C11 113.2(3) . . ? N4 C14 C15 114.9(2) . . ? C16 C15 C14 112.1(3) . . ? O3 N6 O4 122.3(4) . . ? _refine_diff_density_max 0.962 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.060