# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Tong-Bu Lu' _publ_contact_author_email LUTONGBU@MAIL.SYSU.EDU.CN _publ_section_title ; Chiral resolution a racemic macrocyclic complex by recognition one enantiomer over the other: structures and DFT calculations ; loop_ _publ_author_name 'Tong-Bu Lu.' 'Long Jiang.' 'Guang-Chuan Ou.' 'Li-Zi Yang.' data_lambda-1 _database_code_depnum_ccdc_archive 'CCDC 726187' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H49 Cl2 N5 Ni O10' _chemical_formula_weight 673.27 _chemical_absolute_configuration rmad 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 Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 13.3219(9) _cell_length_b 13.3219(9) _cell_length_c 17.576(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3119.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3294 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 23.95 _exptl_crystal_description prism _exptl_crystal_colour violet _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.851 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7551 _exptl_absorpt_correction_T_max 0.8416 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13378 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.05 _reflns_number_total 4955 _reflns_number_gt 3427 _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^)+(0.0359P)^2^+1.1943P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.015(17) _refine_ls_number_reflns 4955 _refine_ls_number_parameters 407 _refine_ls_number_restraints 74 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.88007(4) 0.37905(4) 0.24081(3) 0.01914(15) Uani 1 1 d . . . Cl1 Cl 0.62903(10) 0.33725(11) 0.89570(8) 0.0350(3) Uani 1 1 d . . . N1 N 0.8643(3) 0.3731(3) 0.3615(2) 0.0215(10) Uani 1 1 d . . . H1C H 0.9275 0.3879 0.3808 0.026 Uiso 1 1 calc R . . O1 O 0.9381(2) 0.5327(2) 0.2368(2) 0.0246(8) Uani 1 1 d . . . N3 N 0.8843(3) 0.3768(3) 0.1201(2) 0.0223(11) Uani 1 1 d . . . H3A H 0.9058 0.4405 0.1058 0.027 Uiso 1 1 calc R . . O2 O 1.0357(2) 0.4036(2) 0.26213(18) 0.0238(8) Uani 1 1 d . . . N4 N 0.7266(3) 0.4025(3) 0.2286(2) 0.0244(9) Uani 1 1 d . . . H4D H 0.6953 0.3404 0.2334 0.029 Uiso 1 1 calc R . . N2 N 0.8939(3) 0.2232(3) 0.2468(2) 0.0214(9) Uani 1 1 d . . . H2C H 0.8321 0.1948 0.2350 0.026 Uiso 1 1 calc R . . N5 N 1.1979(3) 0.5039(3) 0.2916(2) 0.0292(10) Uani 1 1 d . . . H5A H 1.1793 0.4535 0.3235 0.044 Uiso 1 1 calc R . . H5B H 1.2454 0.5425 0.3145 0.044 Uiso 1 1 calc R . . H5C H 1.2233 0.4774 0.2479 0.044 Uiso 1 1 calc R . . C19 C 1.1347(4) 0.6415(4) 0.2097(3) 0.0282(13) Uani 1 1 d . . . H19A H 1.2005 0.6720 0.2219 0.034 Uiso 1 1 calc R . . H19B H 1.1429 0.6032 0.1618 0.034 Uiso 1 1 calc R . . C18 C 1.1079(4) 0.5675(4) 0.2730(3) 0.0218(11) Uani 1 1 d . . . H18 H 1.0896 0.6069 0.3195 0.026 Uiso 1 1 calc R . . C5 C 0.9407(4) 0.1992(4) 0.1127(3) 0.0256(12) Uani 1 1 d . . . H5D H 0.8695 0.1791 0.1072 0.031 Uiso 1 1 calc R . . H5E H 0.9807 0.1526 0.0809 0.031 Uiso 1 1 calc R . . C1 C 0.8481(4) 0.2654(4) 0.3779(3) 0.0284(12) Uani 1 1 d . . . H1A H 0.7772 0.2475 0.3681 0.034 Uiso 1 1 calc R . . H1B H 0.8629 0.2517 0.4321 0.034 Uiso 1 1 calc R . . C14 C 0.7934(4) 0.4429(4) 0.4014(3) 0.0268(12) Uani 1 1 d . . . C11 C 0.6765(4) 0.4725(4) 0.2828(3) 0.0246(12) Uani 1 1 d . . . H11 H 0.7085 0.5400 0.2774 0.030 Uiso 1 1 calc R . . C4 C 0.9853(4) 0.0686(4) 0.2070(3) 0.0332(14) Uani 1 1 d . . . H4A H 1.0106 0.0570 0.2586 0.050 Uiso 1 1 calc R . . H4B H 1.0339 0.0430 0.1700 0.050 Uiso 1 1 calc R . . H4C H 0.9211 0.0336 0.2006 0.050 Uiso 1 1 calc R . . C17 C 1.0217(4) 0.4968(4) 0.2549(2) 0.0207(11) Uani 1 1 d . . . C2 C 0.9157(4) 0.2036(4) 0.3283(3) 0.0257(12) Uani 1 1 d . . . H2A H 0.9866 0.2204 0.3394 0.031 Uiso 1 1 calc R . . H2B H 0.9055 0.1315 0.3395 0.031 Uiso 1 1 calc R . . C6 C 0.9517(4) 0.3046(4) 0.0781(3) 0.0287(12) Uani 1 1 d . . . C9 C 0.7778(4) 0.3715(4) 0.0966(3) 0.0366(14) Uani 1 1 d . . . H9A H 0.7546 0.3009 0.0984 0.044 Uiso 1 1 calc R . . H9B H 0.7709 0.3957 0.0436 0.044 Uiso 1 1 calc R . . C7 C 0.9252(4) 0.2988(4) -0.0063(3) 0.0345(13) Uani 1 1 d . . . H7A H 0.8608 0.2642 -0.0125 0.052 Uiso 1 1 calc R . . H7B H 0.9777 0.2617 -0.0334 0.052 Uiso 1 1 calc R . . H7C H 0.9202 0.3669 -0.0272 0.052 Uiso 1 1 calc R . . C13 C 0.6899(4) 0.4379(4) 0.3649(3) 0.0286(12) Uani 1 1 d . . . H13A H 0.6437 0.4781 0.3968 0.034 Uiso 1 1 calc R . . H13B H 0.6669 0.3673 0.3678 0.034 Uiso 1 1 calc R . . C3 C 0.9700(4) 0.1813(4) 0.1945(3) 0.0267(12) Uani 1 1 d . . . H3 H 1.0352 0.2162 0.2042 0.032 Uiso 1 1 calc R . . C16 C 0.7829(4) 0.4139(4) 0.4864(3) 0.0375(13) Uani 1 1 d . . . H16A H 0.7512 0.3477 0.4905 0.056 Uiso 1 1 calc R . . H16B H 0.7412 0.4639 0.5125 0.056 Uiso 1 1 calc R . . H16C H 0.8495 0.4119 0.5100 0.056 Uiso 1 1 calc R . . C15 C 0.8364(4) 0.5484(4) 0.3981(3) 0.0334(13) Uani 1 1 d . . . H15A H 0.9023 0.5494 0.4229 0.050 Uiso 1 1 calc R . . H15B H 0.7911 0.5949 0.4244 0.050 Uiso 1 1 calc R . . H15C H 0.8436 0.5691 0.3448 0.050 Uiso 1 1 calc R . . C8 C 1.0570(4) 0.3432(4) 0.0860(3) 0.0350(14) Uani 1 1 d . . . H8A H 1.0611 0.4111 0.0649 0.053 Uiso 1 1 calc R . . H8B H 1.1031 0.2989 0.0584 0.053 Uiso 1 1 calc R . . H8C H 1.0756 0.3447 0.1400 0.053 Uiso 1 1 calc R . . C12 C 0.5667(4) 0.4834(4) 0.2668(3) 0.0360(14) Uani 1 1 d . . . H12A H 0.5572 0.5053 0.2140 0.054 Uiso 1 1 calc R . . H12B H 0.5378 0.5334 0.3013 0.054 Uiso 1 1 calc R . . H12C H 0.5332 0.4187 0.2744 0.054 Uiso 1 1 calc R . . O6 O 0.6493(3) 0.3156(3) 0.8180(2) 0.0518(12) Uani 1 1 d . . . O5 O 0.5228(3) 0.3420(3) 0.9080(2) 0.0502(12) Uani 1 1 d . . . O4 O 0.6691(3) 0.2611(3) 0.9445(2) 0.0558(12) Uani 1 1 d . . . O3 O 0.6746(3) 0.4314(3) 0.9139(2) 0.0469(11) Uani 1 1 d . . . C10 C 0.7140(4) 0.4350(4) 0.1489(3) 0.0345(14) Uani 1 1 d . . . H10A H 0.7337 0.5064 0.1440 0.041 Uiso 1 1 calc R . . H10B H 0.6425 0.4290 0.1341 0.041 Uiso 1 1 calc R . . C20 C 1.0609(4) 0.7247(4) 0.1956(3) 0.0351(14) Uani 1 1 d . . . H20 H 0.9981 0.6942 0.1749 0.042 Uiso 1 1 calc R . . C22 C 1.1039(5) 0.7963(4) 0.1347(4) 0.0486(17) Uani 1 1 d . . . H22A H 1.0528 0.8460 0.1207 0.073 Uiso 1 1 calc R . . H22B H 1.1230 0.7576 0.0895 0.073 Uiso 1 1 calc R . . H22C H 1.1631 0.8308 0.1550 0.073 Uiso 1 1 calc R . . C21 C 1.0338(6) 0.7821(5) 0.2664(4) 0.062(2) Uani 1 1 d . . . H21A H 0.9966 0.7382 0.3011 0.093 Uiso 1 1 calc R . . H21B H 0.9920 0.8399 0.2528 0.093 Uiso 1 1 calc R . . H21C H 1.0952 0.8056 0.2914 0.093 Uiso 1 1 calc R . . Cl2 Cl 0.62820(9) 0.11472(10) 0.23192(9) 0.0338(3) Uani 0.695(9) 1 d PDU A 1 O9 O 0.6059(5) 0.1658(6) 0.2986(4) 0.058(2) Uani 0.695(9) 1 d PDU A 1 O8 O 0.5476(4) 0.0582(5) 0.2021(4) 0.0414(18) Uani 0.695(9) 1 d PDU A 1 O10 O 0.6523(5) 0.1916(4) 0.1724(3) 0.051(2) Uani 0.695(9) 1 d PDU A 1 O7 O 0.7160(5) 0.0556(6) 0.2397(5) 0.046(2) Uani 0.695(9) 1 d PDU A 1 Cl2' Cl 0.62820(9) 0.11472(10) 0.23192(9) 0.0338(3) Uani 0.305(9) 1 d PDU A 2 O9' O 0.5842(9) 0.0403(10) 0.2986(7) 0.042(4) Uani 0.305(9) 1 d PU A 2 O8' O 0.5521(9) 0.1000(13) 0.1771(8) 0.042(4) Uani 0.305(9) 1 d PDU A 2 O10' O 0.6302(11) 0.2012(10) 0.2717(9) 0.036(4) Uani 0.305(9) 1 d PU A 2 O7' O 0.7217(9) 0.0698(14) 0.2147(10) 0.031(5) Uani 0.305(9) 1 d PDU 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 Ni1 0.0220(4) 0.0186(3) 0.0168(3) 0.0001(3) -0.0027(3) -0.0004(3) Cl1 0.0360(8) 0.0449(9) 0.0240(6) 0.0039(6) 0.0004(6) -0.0105(7) N1 0.022(2) 0.030(3) 0.013(2) -0.0004(18) -0.0012(17) -0.0012(19) O1 0.0292(19) 0.0229(18) 0.0218(18) -0.0022(16) -0.0015(18) 0.0020(14) N3 0.030(3) 0.020(2) 0.017(2) 0.0034(17) -0.0018(18) -0.0024(19) O2 0.025(2) 0.023(2) 0.0236(19) -0.0015(14) -0.0022(14) -0.0001(16) N4 0.026(2) 0.026(2) 0.021(2) 0.0043(19) -0.0043(19) -0.0005(18) N2 0.024(2) 0.020(2) 0.021(2) 0.0024(18) -0.0075(18) -0.0028(17) N5 0.032(3) 0.029(3) 0.026(2) -0.0060(19) -0.0016(19) -0.007(2) C19 0.035(3) 0.020(3) 0.029(3) -0.004(2) 0.006(2) -0.005(2) C18 0.025(3) 0.021(3) 0.019(2) -0.003(2) 0.004(2) 0.003(2) C5 0.026(3) 0.024(3) 0.027(3) -0.008(2) -0.003(2) 0.002(2) C1 0.038(3) 0.030(3) 0.018(3) 0.006(2) -0.001(2) -0.003(3) C14 0.027(3) 0.034(3) 0.020(2) 0.001(2) 0.000(2) 0.002(2) C11 0.023(3) 0.024(3) 0.027(3) 0.003(2) 0.003(2) 0.006(2) C4 0.034(3) 0.025(3) 0.041(3) -0.004(2) -0.012(3) 0.007(3) C17 0.028(3) 0.022(3) 0.012(3) -0.0007(19) 0.0036(19) -0.001(2) C2 0.029(3) 0.020(3) 0.029(3) 0.008(2) -0.010(2) -0.001(2) C6 0.043(3) 0.025(3) 0.018(3) -0.004(2) 0.001(2) 0.003(3) C9 0.048(4) 0.044(4) 0.018(3) -0.003(2) -0.014(2) 0.015(3) C7 0.048(3) 0.032(3) 0.023(3) 0.001(3) 0.002(3) 0.000(3) C13 0.025(3) 0.035(3) 0.025(3) 0.002(2) 0.002(2) 0.010(2) C3 0.032(3) 0.024(3) 0.024(3) 0.001(2) -0.002(2) 0.003(2) C16 0.038(3) 0.053(4) 0.021(3) -0.003(3) 0.001(3) 0.007(3) C15 0.032(3) 0.039(3) 0.029(3) -0.015(3) 0.004(3) 0.001(3) C8 0.045(4) 0.034(3) 0.026(3) -0.004(2) 0.006(3) -0.005(3) C12 0.027(3) 0.048(4) 0.032(3) 0.013(3) 0.005(2) 0.010(3) O6 0.061(3) 0.068(3) 0.026(2) -0.004(2) 0.009(2) -0.006(2) O5 0.039(3) 0.069(3) 0.042(3) 0.003(2) 0.009(2) -0.022(2) O4 0.068(3) 0.064(3) 0.035(3) 0.007(2) -0.010(2) -0.004(2) O3 0.054(3) 0.047(3) 0.039(3) 0.0041(19) 0.006(2) -0.024(2) C10 0.037(3) 0.040(3) 0.026(3) 0.004(3) -0.008(3) 0.010(3) C20 0.035(3) 0.032(3) 0.038(3) 0.005(3) 0.005(3) 0.000(3) C22 0.072(5) 0.030(3) 0.044(4) 0.006(3) 0.009(3) 0.006(3) C21 0.085(6) 0.037(4) 0.064(5) 0.001(3) 0.029(4) 0.022(4) Cl2 0.0278(7) 0.0355(8) 0.0379(8) -0.0151(6) -0.0044(6) 0.0006(6) O9 0.058(4) 0.076(4) 0.041(3) -0.022(3) 0.007(3) -0.005(3) O8 0.037(3) 0.040(3) 0.048(3) -0.009(3) 0.004(3) -0.015(3) O10 0.063(4) 0.038(3) 0.053(3) 0.010(3) -0.004(3) -0.017(3) O7 0.044(4) 0.046(4) 0.048(4) -0.004(3) 0.001(3) 0.009(3) Cl2' 0.0278(7) 0.0355(8) 0.0379(8) -0.0151(6) -0.0044(6) 0.0006(6) O9' 0.040(6) 0.045(6) 0.040(6) 0.006(4) 0.003(4) -0.008(4) O8' 0.045(6) 0.045(6) 0.037(6) 0.003(4) -0.002(4) 0.001(4) O10' 0.041(6) 0.029(5) 0.038(6) -0.003(4) 0.004(4) -0.008(4) O7' 0.029(6) 0.035(6) 0.030(6) 0.003(4) 0.000(4) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N4 2.079(4) . ? Ni1 N2 2.087(4) . ? Ni1 N3 2.123(4) . ? Ni1 O2 2.132(3) . ? Ni1 N1 2.132(4) . ? Ni1 O1 2.189(3) . ? Ni1 C17 2.467(5) . ? Cl1 O6 1.422(4) . ? Cl1 O3 1.430(4) . ? Cl1 O4 1.433(4) . ? Cl1 O5 1.433(4) . ? N1 C1 1.478(6) . ? N1 C14 1.500(6) . ? N1 H1C 0.9300 . ? O1 C17 1.253(6) . ? N3 C9 1.478(6) . ? N3 C6 1.509(6) . ? N3 H3A 0.9300 . ? O2 C17 1.263(6) . ? N4 C10 1.475(6) . ? N4 C11 1.491(6) . ? N4 H4D 0.9300 . ? N2 C3 1.477(6) . ? N2 C2 1.486(6) . ? N2 H2C 0.9300 . ? N5 C18 1.504(6) . ? N5 H5A 0.9100 . ? N5 H5B 0.9100 . ? N5 H5C 0.9100 . ? C19 C20 1.502(7) . ? C19 C18 1.529(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C18 C17 1.518(7) . ? C18 H18 1.0000 . ? C5 C3 1.509(6) . ? C5 C6 1.537(7) . ? C5 H5D 0.9900 . ? C5 H5E 0.9900 . ? C1 C2 1.499(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C14 C15 1.520(7) . ? C14 C13 1.522(7) . ? C14 C16 1.550(7) . ? C11 C12 1.497(7) . ? C11 C13 1.524(7) . ? C11 H11 1.0000 . ? C4 C3 1.532(7) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C6 C8 1.501(7) . ? C6 C7 1.526(7) . ? C9 C10 1.512(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C3 H3 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C20 C21 1.504(8) . ? C20 C22 1.544(8) . ? C20 H20 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? Cl2 O9 1.387(6) . ? Cl2 O8 1.412(5) . ? Cl2 O7 1.417(5) . ? Cl2 O10 1.499(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 N4 Ni1 N2 103.98(15) . . ? N4 Ni1 N3 85.66(16) . . ? N2 Ni1 N3 91.96(16) . . ? N4 Ni1 O2 162.05(14) . . ? N2 Ni1 O2 93.30(14) . . ? N3 Ni1 O2 98.76(14) . . ? N4 Ni1 N1 90.67(16) . . ? N2 Ni1 N1 85.49(16) . . ? N3 Ni1 N1 174.91(15) . . ? O2 Ni1 N1 85.80(14) . . ? N4 Ni1 O1 101.76(14) . . ? N2 Ni1 O1 154.22(14) . . ? N3 Ni1 O1 88.35(14) . . ? O2 Ni1 O1 61.24(12) . . ? N1 Ni1 O1 95.87(15) . . ? N4 Ni1 C17 131.84(16) . . ? N2 Ni1 C17 124.06(16) . . ? N3 Ni1 C17 95.13(15) . . ? O2 Ni1 C17 30.79(14) . . ? N1 Ni1 C17 89.95(15) . . ? O1 Ni1 C17 30.48(13) . . ? O6 Cl1 O3 108.2(2) . . ? O6 Cl1 O4 111.2(3) . . ? O3 Cl1 O4 109.2(3) . . ? O6 Cl1 O5 109.9(3) . . ? O3 Cl1 O5 110.3(3) . . ? O4 Cl1 O5 108.0(3) . . ? C1 N1 C14 114.7(4) . . ? C1 N1 Ni1 104.2(3) . . ? C14 N1 Ni1 120.3(3) . . ? C1 N1 H1C 105.5 . . ? C14 N1 H1C 105.5 . . ? Ni1 N1 H1C 105.5 . . ? C17 O1 Ni1 87.1(3) . . ? C9 N3 C6 113.8(4) . . ? C9 N3 Ni1 104.7(3) . . ? C6 N3 Ni1 120.9(3) . . ? C9 N3 H3A 105.4 . . ? C6 N3 H3A 105.4 . . ? Ni1 N3 H3A 105.4 . . ? C17 O2 Ni1 89.4(3) . . ? C10 N4 C11 111.8(4) . . ? C10 N4 Ni1 104.7(3) . . ? C11 N4 Ni1 117.9(3) . . ? C10 N4 H4D 107.3 . . ? C11 N4 H4D 107.3 . . ? Ni1 N4 H4D 107.3 . . ? C3 N2 C2 113.6(4) . . ? C3 N2 Ni1 113.9(3) . . ? C2 N2 Ni1 103.9(3) . . ? C3 N2 H2C 108.4 . . ? C2 N2 H2C 108.4 . . ? Ni1 N2 H2C 108.4 . . ? C18 N5 H5A 109.5 . . ? C18 N5 H5B 109.5 . . ? H5A N5 H5B 109.5 . . ? C18 N5 H5C 109.5 . . ? H5A N5 H5C 109.5 . . ? H5B N5 H5C 109.5 . . ? C20 C19 C18 116.3(4) . . ? C20 C19 H19A 108.2 . . ? C18 C19 H19A 108.2 . . ? C20 C19 H19B 108.2 . . ? C18 C19 H19B 108.2 . . ? H19A C19 H19B 107.4 . . ? N5 C18 C17 107.4(4) . . ? N5 C18 C19 109.5(4) . . ? C17 C18 C19 115.1(4) . . ? N5 C18 H18 108.2 . . ? C17 C18 H18 108.2 . . ? C19 C18 H18 108.2 . . ? C3 C5 C6 119.7(4) . . ? C3 C5 H5D 107.4 . . ? C6 C5 H5D 107.4 . . ? C3 C5 H5E 107.4 . . ? C6 C5 H5E 107.4 . . ? H5D C5 H5E 106.9 . . ? N1 C1 C2 109.4(4) . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? N1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? N1 C14 C15 108.5(4) . . ? N1 C14 C13 110.3(4) . . ? C15 C14 C13 111.5(4) . . ? N1 C14 C16 110.7(4) . . ? C15 C14 C16 107.5(4) . . ? C13 C14 C16 108.3(4) . . ? N4 C11 C12 112.2(4) . . ? N4 C11 C13 111.3(4) . . ? C12 C11 C13 108.8(4) . . ? N4 C11 H11 108.1 . . ? C12 C11 H11 108.1 . . ? C13 C11 H11 108.1 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O1 C17 O2 122.1(4) . . ? O1 C17 C18 119.3(4) . . ? O2 C17 C18 118.6(4) . . ? O1 C17 Ni1 62.4(2) . . ? O2 C17 Ni1 59.8(2) . . ? C18 C17 Ni1 173.7(3) . . ? N2 C2 C1 110.3(4) . . ? N2 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? N2 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C8 C6 N3 107.0(4) . . ? C8 C6 C7 108.8(4) . . ? N3 C6 C7 111.7(4) . . ? C8 C6 C5 111.4(4) . . ? N3 C6 C5 109.4(4) . . ? C7 C6 C5 108.5(4) . . ? N3 C9 C10 110.0(4) . . ? N3 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? N3 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C14 C13 C11 119.4(4) . . ? C14 C13 H13A 107.5 . . ? C11 C13 H13A 107.5 . . ? C14 C13 H13B 107.5 . . ? C11 C13 H13B 107.5 . . ? H13A C13 H13B 107.0 . . ? N2 C3 C5 110.9(4) . . ? N2 C3 C4 111.8(4) . . ? C5 C3 C4 109.0(4) . . ? N2 C3 H3 108.3 . . ? C5 C3 H3 108.3 . . ? C4 C3 H3 108.3 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N4 C10 C9 110.4(4) . . ? N4 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N4 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C19 C20 C21 113.3(5) . . ? C19 C20 C22 109.1(5) . . ? C21 C20 C22 110.4(5) . . ? C19 C20 H20 107.9 . . ? C21 C20 H20 107.9 . . ? C22 C20 H20 107.9 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O9 Cl2 O8 114.3(4) . . ? O9 Cl2 O7 111.6(5) . . ? O8 Cl2 O7 111.6(5) . . ? O9 Cl2 O10 107.4(4) . . ? O8 Cl2 O10 105.6(4) . . ? O7 Cl2 O10 105.7(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 N4 Ni1 N1 C1 91.2(3) . . . . ? N2 Ni1 N1 C1 -12.8(3) . . . . ? N3 Ni1 N1 C1 47.3(18) . . . . ? O2 Ni1 N1 C1 -106.4(3) . . . . ? O1 Ni1 N1 C1 -166.9(3) . . . . ? C17 Ni1 N1 C1 -137.0(3) . . . . ? N4 Ni1 N1 C14 -39.1(4) . . . . ? N2 Ni1 N1 C14 -143.1(4) . . . . ? N3 Ni1 N1 C14 -83.0(18) . . . . ? O2 Ni1 N1 C14 123.2(4) . . . . ? O1 Ni1 N1 C14 62.8(4) . . . . ? C17 Ni1 N1 C14 92.7(4) . . . . ? N4 Ni1 O1 C17 171.8(3) . . . . ? N2 Ni1 O1 C17 -11.9(5) . . . . ? N3 Ni1 O1 C17 -103.0(3) . . . . ? O2 Ni1 O1 C17 -2.1(2) . . . . ? N1 Ni1 O1 C17 79.8(3) . . . . ? N4 Ni1 N3 C9 -11.4(3) . . . . ? N2 Ni1 N3 C9 92.5(3) . . . . ? O2 Ni1 N3 C9 -173.9(3) . . . . ? N1 Ni1 N3 C9 32.6(18) . . . . ? O1 Ni1 N3 C9 -113.3(3) . . . . ? C17 Ni1 N3 C9 -143.1(3) . . . . ? N4 Ni1 N3 C6 -141.4(4) . . . . ? N2 Ni1 N3 C6 -37.5(4) . . . . ? O2 Ni1 N3 C6 56.1(4) . . . . ? N1 Ni1 N3 C6 -97.4(17) . . . . ? O1 Ni1 N3 C6 116.7(4) . . . . ? C17 Ni1 N3 C6 86.9(4) . . . . ? N4 Ni1 O2 C17 -17.9(6) . . . . ? N2 Ni1 O2 C17 177.8(3) . . . . ? N3 Ni1 O2 C17 85.3(3) . . . . ? N1 Ni1 O2 C17 -97.0(3) . . . . ? O1 Ni1 O2 C17 2.1(2) . . . . ? N2 Ni1 N4 C10 -107.9(3) . . . . ? N3 Ni1 N4 C10 -17.0(3) . . . . ? O2 Ni1 N4 C10 88.2(5) . . . . ? N1 Ni1 N4 C10 166.5(3) . . . . ? O1 Ni1 N4 C10 70.4(3) . . . . ? C17 Ni1 N4 C10 76.0(4) . . . . ? N2 Ni1 N4 C11 127.0(3) . . . . ? N3 Ni1 N4 C11 -142.0(3) . . . . ? O2 Ni1 N4 C11 -36.9(7) . . . . ? N1 Ni1 N4 C11 41.5(3) . . . . ? O1 Ni1 N4 C11 -54.6(3) . . . . ? C17 Ni1 N4 C11 -49.0(4) . . . . ? N4 Ni1 N2 C3 129.9(3) . . . . ? N3 Ni1 N2 C3 43.9(3) . . . . ? O2 Ni1 N2 C3 -55.0(3) . . . . ? N1 Ni1 N2 C3 -140.6(3) . . . . ? O1 Ni1 N2 C3 -46.4(5) . . . . ? C17 Ni1 N2 C3 -53.7(4) . . . . ? N4 Ni1 N2 C2 -106.0(3) . . . . ? N3 Ni1 N2 C2 167.9(3) . . . . ? O2 Ni1 N2 C2 69.0(3) . . . . ? N1 Ni1 N2 C2 -16.5(3) . . . . ? O1 Ni1 N2 C2 77.7(5) . . . . ? C17 Ni1 N2 C2 70.4(3) . . . . ? C20 C19 C18 N5 -167.5(5) . . . . ? C20 C19 C18 C17 71.4(6) . . . . ? C14 N1 C1 C2 173.8(4) . . . . ? Ni1 N1 C1 C2 40.3(4) . . . . ? C1 N1 C14 C15 163.7(4) . . . . ? Ni1 N1 C14 C15 -70.8(5) . . . . ? C1 N1 C14 C13 -73.9(5) . . . . ? Ni1 N1 C14 C13 51.6(5) . . . . ? C1 N1 C14 C16 45.9(6) . . . . ? Ni1 N1 C14 C16 171.5(3) . . . . ? C10 N4 C11 C12 57.7(5) . . . . ? Ni1 N4 C11 C12 179.2(3) . . . . ? C10 N4 C11 C13 179.9(4) . . . . ? Ni1 N4 C11 C13 -58.7(5) . . . . ? Ni1 O1 C17 O2 3.6(4) . . . . ? Ni1 O1 C17 C18 -173.1(4) . . . . ? Ni1 O2 C17 O1 -3.7(4) . . . . ? Ni1 O2 C17 C18 173.0(4) . . . . ? N5 C18 C17 O1 -179.2(4) . . . . ? C19 C18 C17 O1 -57.0(6) . . . . ? N5 C18 C17 O2 4.0(6) . . . . ? C19 C18 C17 O2 126.2(5) . . . . ? N5 C18 C17 Ni1 77(3) . . . . ? C19 C18 C17 Ni1 -161(3) . . . . ? N4 Ni1 C17 O1 -10.9(3) . . . . ? N2 Ni1 C17 O1 173.8(2) . . . . ? N3 Ni1 C17 O1 77.9(3) . . . . ? O2 Ni1 C17 O1 176.4(4) . . . . ? N1 Ni1 C17 O1 -101.7(3) . . . . ? N4 Ni1 C17 O2 172.7(2) . . . . ? N2 Ni1 C17 O2 -2.7(3) . . . . ? N3 Ni1 C17 O2 -98.5(3) . . . . ? N1 Ni1 C17 O2 81.9(3) . . . . ? O1 Ni1 C17 O2 -176.4(4) . . . . ? N4 Ni1 C17 C18 96(3) . . . . ? N2 Ni1 C17 C18 -79(3) . . . . ? N3 Ni1 C17 C18 -175(3) . . . . ? O2 Ni1 C17 C18 -77(3) . . . . ? N1 Ni1 C17 C18 5(3) . . . . ? O1 Ni1 C17 C18 107(3) . . . . ? C3 N2 C2 C1 168.4(4) . . . . ? Ni1 N2 C2 C1 44.1(4) . . . . ? N1 C1 C2 N2 -59.7(5) . . . . ? C9 N3 C6 C8 159.8(4) . . . . ? Ni1 N3 C6 C8 -74.2(4) . . . . ? C9 N3 C6 C7 40.8(6) . . . . ? Ni1 N3 C6 C7 166.7(3) . . . . ? C9 N3 C6 C5 -79.3(5) . . . . ? Ni1 N3 C6 C5 46.6(5) . . . . ? C3 C5 C6 C8 55.5(6) . . . . ? C3 C5 C6 N3 -62.6(6) . . . . ? C3 C5 C6 C7 175.3(4) . . . . ? C6 N3 C9 C10 171.9(4) . . . . ? Ni1 N3 C9 C10 37.8(5) . . . . ? N1 C14 C13 C11 -64.5(6) . . . . ? C15 C14 C13 C11 56.1(6) . . . . ? C16 C14 C13 C11 174.2(5) . . . . ? N4 C11 C13 C14 69.3(6) . . . . ? C12 C11 C13 C14 -166.6(5) . . . . ? C2 N2 C3 C5 177.0(4) . . . . ? Ni1 N2 C3 C5 -64.2(5) . . . . ? C2 N2 C3 C4 55.1(5) . . . . ? Ni1 N2 C3 C4 173.9(3) . . . . ? C6 C5 C3 N2 75.0(6) . . . . ? C6 C5 C3 C4 -161.5(5) . . . . ? C11 N4 C10 C9 171.8(4) . . . . ? Ni1 N4 C10 C9 43.0(5) . . . . ? N3 C9 C10 N4 -57.0(6) . . . . ? C18 C19 C20 C21 52.1(7) . . . . ? C18 C19 C20 C22 175.6(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5C O4 0.91 2.22 2.989(6) 141.4 4_664 N5 H5C O5 0.91 2.24 3.054(6) 149.2 4_664 N5 H5B O3 0.91 2.08 2.872(6) 145.6 2_764 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.413 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.076 data_S-2 _database_code_depnum_ccdc_archive 'CCDC 726188' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H38 Cl2 N4 Ni O9' _chemical_formula_weight 560.11 _chemical_absolute_configuration rmad 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0179(16) _cell_length_b 13.353(2) _cell_length_c 10.3602(19) _cell_angle_alpha 90.00 _cell_angle_beta 107.875(3) _cell_angle_gamma 90.00 _cell_volume 1187.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2474 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 1.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6384 _exptl_absorpt_correction_T_max 0.7867 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6639 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0608 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.14 _reflns_number_total 4648 _reflns_number_gt 3901 _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^)+(0.0690P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.021(18) _refine_ls_number_reflns 4648 _refine_ls_number_parameters 295 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1089 _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 Ni1 Ni 0.67960(6) 0.39563(4) 0.82733(5) 0.01709(13) Uani 1 1 d . . . Cl1 Cl 0.27222(13) 0.51212(9) 0.07013(12) 0.0290(3) Uani 1 1 d . . . Cl2 Cl 0.96266(16) 0.54410(11) 0.64691(13) 0.0397(3) Uani 1 1 d . . . N3 N 0.8489(4) 0.3920(3) 0.9969(3) 0.0175(6) Uani 1 1 d . . . H3A H 0.9174 0.4421 0.9897 0.021 Uiso 1 1 calc R . . N1 N 0.5203(4) 0.4059(3) 0.6538(3) 0.0223(8) Uani 1 1 d . . . H1C H 0.5716 0.4279 0.5937 0.027 Uiso 1 1 calc R . . N4 N 0.7646(4) 0.2757(3) 0.7768(3) 0.0208(8) Uani 1 1 d . . . H4D H 0.7160 0.2218 0.8040 0.025 Uiso 1 1 calc R . . N2 N 0.5968(4) 0.5178(3) 0.8772(3) 0.0186(7) Uani 1 1 d . . . H2C H 0.5240 0.4999 0.9201 0.022 Uiso 1 1 calc R . . C8 C 0.9437(5) 0.3989(5) 1.2508(4) 0.0284(9) Uani 1 1 d . . . H8A H 0.9687 0.3273 1.2590 0.043 Uiso 1 1 calc R . . H8B H 0.9162 0.4211 1.3307 0.043 Uiso 1 1 calc R . . H8C H 1.0344 0.4366 1.2445 0.043 Uiso 1 1 calc R . . C5 C 0.7634(5) 0.5296(3) 1.1155(4) 0.0228(9) Uani 1 1 d . . . H5A H 0.8543 0.5661 1.1752 0.027 Uiso 1 1 calc R . . H5B H 0.6764 0.5384 1.1540 0.027 Uiso 1 1 calc R . . C4 C 0.6612(6) 0.6860(4) 0.9830(5) 0.0276(10) Uani 1 1 d . . . H4A H 0.6555 0.7221 0.8992 0.041 Uiso 1 1 calc R . . H4B H 0.7344 0.7201 1.0602 0.041 Uiso 1 1 calc R . . H4C H 0.5578 0.6843 0.9953 0.041 Uiso 1 1 calc R . . C14 C 0.4417(5) 0.3095(4) 0.5943(5) 0.0248(10) Uani 1 1 d . . . C3 C 0.7165(5) 0.5804(3) 0.9739(4) 0.0195(9) Uani 1 1 d . . . H3 H 0.8106 0.5833 0.9422 0.023 Uiso 1 1 calc R . . C1 C 0.4117(6) 0.4883(4) 0.6599(5) 0.0302(11) Uani 1 1 d . . . H1A H 0.3319 0.4641 0.7001 0.036 Uiso 1 1 calc R . . H1B H 0.3586 0.5144 0.5678 0.036 Uiso 1 1 calc R . . C9 C 0.9365(6) 0.2959(3) 1.0035(5) 0.0257(10) Uani 1 1 d . . . H9A H 0.8864 0.2414 1.0398 0.031 Uiso 1 1 calc R . . H9B H 1.0454 0.3034 1.0626 0.031 Uiso 1 1 calc R . . C2 C 0.5103(6) 0.5686(3) 0.7473(5) 0.0283(11) Uani 1 1 d . . . H2A H 0.5838 0.5972 0.7032 0.034 Uiso 1 1 calc R . . H2B H 0.4441 0.6231 0.7640 0.034 Uiso 1 1 calc R . . C7 C 0.6707(6) 0.3514(4) 1.1275(5) 0.0274(10) Uani 1 1 d . . . H7A H 0.5775 0.3690 1.0528 0.041 Uiso 1 1 calc R . . H7B H 0.6501 0.3614 1.2142 0.041 Uiso 1 1 calc R . . H7C H 0.6973 0.2811 1.1190 0.041 Uiso 1 1 calc R . . C10 C 0.9322(5) 0.2734(4) 0.8598(5) 0.0262(10) Uani 1 1 d . . . H10A H 0.9919 0.3243 0.8270 0.031 Uiso 1 1 calc R . . H10B H 0.9777 0.2066 0.8544 0.031 Uiso 1 1 calc R . . C15 C 0.3801(6) 0.2587(4) 0.6982(5) 0.0311(11) Uani 1 1 d . . . H15A H 0.4676 0.2394 0.7771 0.047 Uiso 1 1 calc R . . H15B H 0.3210 0.1988 0.6580 0.047 Uiso 1 1 calc R . . H15C H 0.3119 0.3050 0.7268 0.047 Uiso 1 1 calc R . . C6 C 0.8048(5) 0.4172(3) 1.1221(4) 0.0228(10) Uani 1 1 d . . . C16 C 0.3028(7) 0.3270(4) 0.4659(5) 0.0393(13) Uani 1 1 d . . . H16A H 0.2244 0.3682 0.4887 0.059 Uiso 1 1 calc R . . H16B H 0.2568 0.2624 0.4298 0.059 Uiso 1 1 calc R . . H16C H 0.3388 0.3615 0.3976 0.059 Uiso 1 1 calc R . . C11 C 0.7381(6) 0.2648(4) 0.6272(5) 0.0273(11) Uani 1 1 d . . . H11 H 0.7666 0.3298 0.5931 0.033 Uiso 1 1 calc R . . C13 C 0.5654(6) 0.2459(4) 0.5551(5) 0.0304(11) Uani 1 1 d . . . H13A H 0.5442 0.1746 0.5690 0.036 Uiso 1 1 calc R . . H13B H 0.5478 0.2551 0.4567 0.036 Uiso 1 1 calc R . . O1 O 0.1137(4) 0.5406(3) 0.0446(4) 0.0420(9) Uani 1 1 d . . . O1W O 0.5972(6) 0.4809(4) 0.4216(5) 0.0641(13) Uani 1 1 d . . . O6 O 0.8831(6) 0.5798(4) 0.5140(5) 0.0715(15) Uani 1 1 d . . . O7 O 0.8648(6) 0.5259(4) 0.7267(5) 0.0688(14) Uani 1 1 d . . . O5 O 1.0357(6) 0.4522(4) 0.6318(6) 0.0663(14) Uani 1 1 d . . . O8 O 1.0836(7) 0.6156(4) 0.7108(5) 0.0746(16) Uani 1 1 d . . . O4 O 0.3017(6) 0.4602(5) -0.0405(6) 0.0826(18) Uani 1 1 d . . . O3 O 0.3679(7) 0.5931(5) 0.0971(13) 0.182(5) Uani 1 1 d . . . O2 O 0.3134(8) 0.4432(8) 0.1771(8) 0.158(5) Uani 1 1 d . . . C12 C 0.8367(7) 0.1833(5) 0.5921(6) 0.0443(14) Uani 1 1 d . . . H12A H 0.9473 0.2001 0.6311 0.067 Uiso 1 1 calc R . . H12B H 0.8108 0.1779 0.4933 0.067 Uiso 1 1 calc R . . H12C H 0.8156 0.1192 0.6291 0.067 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0165(2) 0.0168(2) 0.0169(2) -0.0008(2) 0.00366(18) 0.0019(2) Cl1 0.0196(5) 0.0354(6) 0.0318(6) -0.0032(5) 0.0077(5) -0.0045(5) Cl2 0.0445(8) 0.0445(8) 0.0333(7) 0.0082(6) 0.0169(6) 0.0020(6) N3 0.0167(15) 0.0143(14) 0.0214(15) -0.0004(19) 0.0057(13) 0.0015(19) N1 0.0190(17) 0.026(2) 0.0187(15) 0.0000(18) 0.0013(13) 0.0001(18) N4 0.021(2) 0.0207(19) 0.0194(18) -0.0039(15) 0.0045(16) 0.0010(15) N2 0.0176(18) 0.0200(18) 0.0177(17) 0.0049(15) 0.0047(14) 0.0043(15) C8 0.021(2) 0.035(2) 0.026(2) 0.010(3) 0.0025(17) 0.000(3) C5 0.018(2) 0.026(2) 0.022(2) -0.0039(18) 0.0033(18) -0.0042(18) C4 0.025(3) 0.023(2) 0.033(2) 0.001(2) 0.007(2) 0.001(2) C14 0.020(2) 0.024(2) 0.024(2) -0.0005(19) -0.0024(19) 0.0019(18) C3 0.016(2) 0.019(2) 0.027(2) -0.0016(18) 0.0121(18) 0.0013(16) C1 0.024(3) 0.035(3) 0.024(2) 0.001(2) -0.004(2) 0.011(2) C9 0.024(2) 0.024(2) 0.027(2) 0.0001(19) 0.005(2) 0.008(2) C2 0.032(3) 0.023(2) 0.027(2) 0.0083(19) 0.006(2) 0.013(2) C7 0.029(3) 0.027(2) 0.026(2) 0.0004(19) 0.009(2) -0.006(2) C10 0.017(2) 0.026(2) 0.032(3) -0.006(2) 0.003(2) 0.0068(18) C15 0.024(3) 0.039(3) 0.030(3) 0.000(2) 0.007(2) -0.005(2) C6 0.021(2) 0.026(3) 0.0190(19) -0.0015(17) 0.0030(17) -0.0047(17) C16 0.038(3) 0.047(3) 0.025(3) -0.001(2) -0.001(2) 0.000(3) C11 0.028(3) 0.030(3) 0.024(2) -0.007(2) 0.008(2) -0.002(2) C13 0.036(3) 0.029(3) 0.024(2) -0.002(2) 0.006(2) 0.002(2) O1 0.0230(18) 0.041(2) 0.064(3) 0.005(2) 0.0162(18) -0.0013(16) O1W 0.063(3) 0.082(4) 0.044(3) 0.012(2) 0.013(2) -0.018(3) O6 0.069(3) 0.084(4) 0.052(3) 0.025(3) 0.005(2) -0.008(3) O7 0.060(3) 0.098(4) 0.065(3) -0.007(3) 0.045(3) -0.014(3) O5 0.057(3) 0.060(3) 0.087(4) -0.009(3) 0.029(3) 0.014(2) O8 0.105(4) 0.063(3) 0.061(3) -0.008(2) 0.033(3) -0.039(3) O4 0.048(3) 0.126(5) 0.071(3) -0.028(3) 0.014(3) 0.016(3) O3 0.042(3) 0.081(4) 0.434(16) -0.103(7) 0.088(6) -0.032(3) O2 0.086(5) 0.278(13) 0.135(6) 0.130(7) 0.073(5) 0.091(6) C12 0.042(3) 0.053(4) 0.038(3) -0.017(3) 0.011(3) 0.007(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 Ni1 N4 1.917(4) . ? Ni1 N2 1.930(4) . ? Ni1 N1 1.931(3) . ? Ni1 N3 1.943(3) . ? Cl1 O3 1.358(6) . ? Cl1 O2 1.400(7) . ? Cl1 O1 1.423(4) . ? Cl1 O4 1.432(5) . ? Cl2 O7 1.404(4) . ? Cl2 O5 1.425(5) . ? Cl2 O6 1.425(5) . ? Cl2 O8 1.447(5) . ? N3 C9 1.497(6) . ? N3 C6 1.507(5) . ? N3 H3A 0.9300 . ? N1 C1 1.487(6) . ? N1 C14 1.507(6) . ? N1 H1C 0.9300 . ? N4 C10 1.492(6) . ? N4 C11 1.500(6) . ? N4 H4D 0.9300 . ? N2 C3 1.485(6) . ? N2 C2 1.494(5) . ? N2 H2C 0.9300 . ? C8 C6 1.543(6) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C5 C6 1.543(6) . ? C5 C3 1.553(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C4 C3 1.507(6) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C14 C15 1.515(7) . ? C14 C16 1.539(7) . ? C14 C13 1.552(7) . ? C3 H3 1.0000 . ? C1 C2 1.505(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C9 C10 1.508(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C7 C6 1.510(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C11 C12 1.519(7) . ? C11 C13 1.528(7) . ? C11 H11 1.0000 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ni1 N2 178.95(17) . . ? N4 Ni1 N1 92.89(16) . . ? N2 Ni1 N1 87.19(17) . . ? N4 Ni1 N3 87.53(16) . . ? N2 Ni1 N3 92.32(16) . . ? N1 Ni1 N3 175.85(18) . . ? O3 Cl1 O2 111.3(7) . . ? O3 Cl1 O1 111.3(3) . . ? O2 Cl1 O1 109.3(3) . . ? O3 Cl1 O4 106.7(5) . . ? O2 Cl1 O4 104.2(5) . . ? O1 Cl1 O4 113.7(3) . . ? O7 Cl2 O5 108.2(3) . . ? O7 Cl2 O6 113.9(3) . . ? O5 Cl2 O6 107.1(3) . . ? O7 Cl2 O8 111.5(3) . . ? O5 Cl2 O8 108.0(3) . . ? O6 Cl2 O8 107.8(3) . . ? C9 N3 C6 115.3(3) . . ? C9 N3 Ni1 108.7(3) . . ? C6 N3 Ni1 115.5(2) . . ? C9 N3 H3A 105.4 . . ? C6 N3 H3A 105.4 . . ? Ni1 N3 H3A 105.4 . . ? C1 N1 C14 114.6(3) . . ? C1 N1 Ni1 108.9(3) . . ? C14 N1 Ni1 116.2(3) . . ? C1 N1 H1C 105.3 . . ? C14 N1 H1C 105.3 . . ? Ni1 N1 H1C 105.3 . . ? C10 N4 C11 113.9(4) . . ? C10 N4 Ni1 106.2(3) . . ? C11 N4 Ni1 114.4(3) . . ? C10 N4 H4D 107.3 . . ? C11 N4 H4D 107.3 . . ? Ni1 N4 H4D 107.3 . . ? C3 N2 C2 115.0(3) . . ? C3 N2 Ni1 113.3(2) . . ? C2 N2 Ni1 106.2(3) . . ? C3 N2 H2C 107.3 . . ? C2 N2 H2C 107.3 . . ? Ni1 N2 H2C 107.3 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C5 C3 117.3(3) . . ? C6 C5 H5A 108.0 . . ? C3 C5 H5A 108.0 . . ? C6 C5 H5B 108.0 . . ? C3 C5 H5B 108.0 . . ? H5A C5 H5B 107.2 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C14 C15 108.7(4) . . ? N1 C14 C16 112.3(4) . . ? C15 C14 C16 107.7(4) . . ? N1 C14 C13 106.8(4) . . ? C15 C14 C13 113.0(4) . . ? C16 C14 C13 108.5(4) . . ? N2 C3 C4 112.5(4) . . ? N2 C3 C5 108.8(3) . . ? C4 C3 C5 110.4(4) . . ? N2 C3 H3 108.3 . . ? C4 C3 H3 108.3 . . ? C5 C3 H3 108.3 . . ? N1 C1 C2 106.1(4) . . ? N1 C1 H1A 110.5 . . ? C2 C1 H1A 110.5 . . ? N1 C1 H1B 110.5 . . ? C2 C1 H1B 110.5 . . ? H1A C1 H1B 108.7 . . ? N3 C9 C10 105.8(3) . . ? N3 C9 H9A 110.6 . . ? C10 C9 H9A 110.6 . . ? N3 C9 H9B 110.6 . . ? C10 C9 H9B 110.6 . . ? H9A C9 H9B 108.7 . . ? N2 C2 C1 105.5(4) . . ? N2 C2 H2A 110.6 . . ? C1 C2 H2A 110.6 . . ? N2 C2 H2B 110.6 . . ? C1 C2 H2B 110.6 . . ? H2A C2 H2B 108.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N4 C10 C9 106.3(4) . . ? N4 C10 H10A 110.5 . . ? C9 C10 H10A 110.5 . . ? N4 C10 H10B 110.5 . . ? C9 C10 H10B 110.5 . . ? H10A C10 H10B 108.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C6 C7 109.1(4) . . ? N3 C6 C5 107.7(4) . . ? C7 C6 C5 112.5(4) . . ? N3 C6 C8 110.4(3) . . ? C7 C6 C8 108.8(4) . . ? C5 C6 C8 108.3(4) . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N4 C11 C12 113.4(4) . . ? N4 C11 C13 109.7(4) . . ? C12 C11 C13 110.4(4) . . ? N4 C11 H11 107.7 . . ? C12 C11 H11 107.7 . . ? C13 C11 H11 107.7 . . ? C11 C13 C14 119.2(4) . . ? C11 C13 H13A 107.5 . . ? C14 C13 H13A 107.5 . . ? C11 C13 H13B 107.5 . . ? C14 C13 H13B 107.5 . . ? H13A C13 H13B 107.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 N4 Ni1 N3 C9 -7.0(3) . . . . ? N2 Ni1 N3 C9 174.1(3) . . . . ? N1 Ni1 N3 C9 -103(3) . . . . ? N4 Ni1 N3 C6 -138.4(3) . . . . ? N2 Ni1 N3 C6 42.6(3) . . . . ? N1 Ni1 N3 C6 126(3) . . . . ? N4 Ni1 N1 C1 172.8(3) . . . . ? N2 Ni1 N1 C1 -8.2(3) . . . . ? N3 Ni1 N1 C1 -91(3) . . . . ? N4 Ni1 N1 C14 41.5(3) . . . . ? N2 Ni1 N1 C14 -139.5(3) . . . . ? N3 Ni1 N1 C14 137(3) . . . . ? N2 Ni1 N4 C10 59(9) . . . . ? N1 Ni1 N4 C10 153.2(3) . . . . ? N3 Ni1 N4 C10 -22.6(3) . . . . ? N2 Ni1 N4 C11 -67(9) . . . . ? N1 Ni1 N4 C11 26.7(3) . . . . ? N3 Ni1 N4 C11 -149.1(3) . . . . ? N4 Ni1 N2 C3 -55(9) . . . . ? N1 Ni1 N2 C3 -149.0(3) . . . . ? N3 Ni1 N2 C3 26.8(3) . . . . ? N4 Ni1 N2 C2 72(9) . . . . ? N1 Ni1 N2 C2 -21.8(3) . . . . ? N3 Ni1 N2 C2 154.1(3) . . . . ? C1 N1 C14 C15 -75.0(5) . . . . ? Ni1 N1 C14 C15 53.5(4) . . . . ? C1 N1 C14 C16 44.0(6) . . . . ? Ni1 N1 C14 C16 172.5(3) . . . . ? C1 N1 C14 C13 162.7(3) . . . . ? Ni1 N1 C14 C13 -68.7(4) . . . . ? C2 N2 C3 C4 42.2(5) . . . . ? Ni1 N2 C3 C4 164.7(3) . . . . ? C2 N2 C3 C5 164.9(3) . . . . ? Ni1 N2 C3 C5 -72.6(3) . . . . ? C6 C5 C3 N2 49.2(5) . . . . ? C6 C5 C3 C4 173.1(4) . . . . ? C14 N1 C1 C2 168.4(4) . . . . ? Ni1 N1 C1 C2 36.2(4) . . . . ? C6 N3 C9 C10 166.1(4) . . . . ? Ni1 N3 C9 C10 34.6(4) . . . . ? C3 N2 C2 C1 173.0(4) . . . . ? Ni1 N2 C2 C1 46.8(4) . . . . ? N1 C1 C2 N2 -54.3(5) . . . . ? C11 N4 C10 C9 174.2(4) . . . . ? Ni1 N4 C10 C9 47.5(4) . . . . ? N3 C9 C10 N4 -53.7(5) . . . . ? C9 N3 C6 C7 -74.9(5) . . . . ? Ni1 N3 C6 C7 53.3(4) . . . . ? C9 N3 C6 C5 162.7(4) . . . . ? Ni1 N3 C6 C5 -69.0(4) . . . . ? C9 N3 C6 C8 44.7(5) . . . . ? Ni1 N3 C6 C8 172.9(3) . . . . ? C3 C5 C6 N3 21.5(5) . . . . ? C3 C5 C6 C7 -98.7(5) . . . . ? C3 C5 C6 C8 140.9(4) . . . . ? C10 N4 C11 C12 44.2(6) . . . . ? Ni1 N4 C11 C12 166.6(4) . . . . ? C10 N4 C11 C13 168.1(4) . . . . ? Ni1 N4 C11 C13 -69.5(4) . . . . ? N4 C11 C13 C14 44.3(6) . . . . ? C12 C11 C13 C14 169.9(4) . . . . ? N1 C14 C13 C11 24.0(6) . . . . ? C15 C14 C13 C11 -95.4(5) . . . . ? C16 C14 C13 C11 145.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.843 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.093 data_R-2 _database_code_depnum_ccdc_archive 'CCDC 726189' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H38 Cl2 N4 Ni O9' _chemical_formula_weight 560.11 _chemical_absolute_configuration rmad 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0136(14) _cell_length_b 13.371(2) _cell_length_c 10.3537(16) _cell_angle_alpha 90.00 _cell_angle_beta 107.859(2) _cell_angle_gamma 90.00 _cell_volume 1187.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4351 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.06 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 1.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6214 _exptl_absorpt_correction_T_max 0.8026 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6663 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.07 _reflns_number_total 4808 _reflns_number_gt 4362 _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^)+(0.0634P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(15) _refine_ls_number_reflns 4808 _refine_ls_number_parameters 295 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.67970(4) 0.74573(3) 0.82720(4) 0.01760(11) Uani 1 1 d . . . Cl1 Cl 0.96271(13) 0.59722(9) 0.64683(11) 0.0406(3) Uani 1 1 d . . . N1 N 0.8489(3) 0.7489(3) 0.9968(2) 0.0186(5) Uani 1 1 d . . . H1C H 0.9175 0.6989 0.9895 0.022 Uiso 1 1 calc R . . N3 N 0.5205(3) 0.7349(3) 0.6529(3) 0.0217(6) Uani 1 1 d . . . H3A H 0.5717 0.7130 0.5926 0.026 Uiso 1 1 calc R . . N2 N 0.7646(3) 0.8661(2) 0.7765(3) 0.0210(6) Uani 1 1 d . . . H2C H 0.7156 0.9199 0.8035 0.025 Uiso 1 1 calc R . . N4 N 0.5964(3) 0.6234(2) 0.8774(3) 0.0195(6) Uani 1 1 d . . . H4D H 0.5233 0.6412 0.9201 0.023 Uiso 1 1 calc R . . C16 C 0.9435(4) 0.7429(4) 1.2509(3) 0.0292(7) Uani 1 1 d . . . H16A H 1.0350 0.7059 1.2447 0.044 Uiso 1 1 calc R . . H16B H 0.9162 0.7203 1.3307 0.044 Uiso 1 1 calc R . . H16C H 0.9674 0.8146 1.2592 0.044 Uiso 1 1 calc R . . C12 C 0.6612(4) 0.4551(3) 0.9827(4) 0.0270(8) Uani 1 1 d . . . H12A H 0.5593 0.4564 0.9982 0.041 Uiso 1 1 calc R . . H12B H 0.7365 0.4204 1.0580 0.041 Uiso 1 1 calc R . . H12C H 0.6523 0.4199 0.8976 0.041 Uiso 1 1 calc R . . C13 C 0.7637(4) 0.6117(3) 1.1144(4) 0.0221(7) Uani 1 1 d . . . H13A H 0.6772 0.6028 1.1536 0.026 Uiso 1 1 calc R . . H13B H 0.8549 0.5753 1.1737 0.026 Uiso 1 1 calc R . . C1 C 0.9364(4) 0.8454(3) 1.0031(4) 0.0245(8) Uani 1 1 d . . . H1A H 0.8858 0.8998 1.0392 0.029 Uiso 1 1 calc R . . H1B H 1.0452 0.8382 1.0625 0.029 Uiso 1 1 calc R . . C6 C 0.4419(4) 0.8327(3) 0.5945(4) 0.0262(8) Uani 1 1 d . . . C11 C 0.7158(4) 0.5606(3) 0.9737(4) 0.0210(7) Uani 1 1 d . . . H11 H 0.8096 0.5578 0.9415 0.025 Uiso 1 1 calc R . . C9 C 0.4117(5) 0.6533(3) 0.6596(4) 0.0312(9) Uani 1 1 d . . . H9A H 0.3578 0.6272 0.5676 0.037 Uiso 1 1 calc R . . H9B H 0.3326 0.6776 0.7005 0.037 Uiso 1 1 calc R . . C10 C 0.5108(5) 0.5728(3) 0.7467(4) 0.0294(8) Uani 1 1 d . . . H10A H 0.4448 0.5179 0.7627 0.035 Uiso 1 1 calc R . . H10B H 0.5849 0.5449 0.7027 0.035 Uiso 1 1 calc R . . C2 C 0.9326(4) 0.8680(3) 0.8608(4) 0.0248(8) Uani 1 1 d . . . H2A H 0.9925 0.8171 0.8281 0.030 Uiso 1 1 calc R . . H2B H 0.9785 0.9346 0.8559 0.030 Uiso 1 1 calc R . . C3 C 0.7379(4) 0.8760(3) 0.6272(4) 0.0276(8) Uani 1 1 d . . . H3 H 0.7664 0.8110 0.5932 0.033 Uiso 1 1 calc R . . C7 C 0.3034(5) 0.8135(4) 0.4659(4) 0.0405(11) Uani 1 1 d . . . H7A H 0.3400 0.7778 0.3988 0.061 Uiso 1 1 calc R . . H7B H 0.2575 0.8776 0.4277 0.061 Uiso 1 1 calc R . . H7C H 0.2247 0.7731 0.4893 0.061 Uiso 1 1 calc R . . C15 C 0.6708(4) 0.7905(3) 1.1271(4) 0.0276(8) Uani 1 1 d . . . H15A H 0.6992 0.8608 1.1213 0.041 Uiso 1 1 calc R . . H15B H 0.6480 0.7793 1.2126 0.041 Uiso 1 1 calc R . . H15C H 0.5785 0.7745 1.0508 0.041 Uiso 1 1 calc R . . C8 C 0.3816(5) 0.8824(3) 0.6986(4) 0.0322(9) Uani 1 1 d . . . H8A H 0.3117 0.8365 0.7256 0.048 Uiso 1 1 calc R . . H8B H 0.3244 0.9432 0.6597 0.048 Uiso 1 1 calc R . . H8C H 0.4693 0.9000 0.7782 0.048 Uiso 1 1 calc R . . C5 C 0.5657(5) 0.8957(3) 0.5547(4) 0.0315(9) Uani 1 1 d . . . H5A H 0.5480 0.8863 0.4563 0.038 Uiso 1 1 calc R . . H5B H 0.5451 0.9670 0.5686 0.038 Uiso 1 1 calc R . . C14 C 0.8052(4) 0.7240(2) 1.1219(3) 0.0211(7) Uani 1 1 d . . . Cl2 Cl 0.72790(10) 0.12916(7) 0.92971(10) 0.0298(2) Uani 1 1 d . . . O5 O 0.8865(3) 0.1005(2) 0.9554(4) 0.0424(7) Uani 1 1 d . . . O1 O 0.8830(5) 0.5611(4) 0.5140(4) 0.0710(12) Uani 1 1 d . . . O1W O 0.5979(5) 0.6603(3) 0.4215(4) 0.0645(11) Uani 1 1 d . . . O4 O 0.8645(5) 0.6157(4) 0.7272(4) 0.0688(12) Uani 1 1 d . . . O2 O 1.0844(6) 0.5260(3) 0.7115(4) 0.0747(13) Uani 1 1 d . . . O3 O 1.0355(5) 0.6894(3) 0.6313(5) 0.0687(11) Uani 1 1 d . . . O7 O 0.6980(5) 0.1806(4) 1.0408(5) 0.0809(15) Uani 1 1 d . . . O8 O 0.6318(6) 0.0478(5) 0.9022(12) 0.180(5) Uani 1 1 d . . . O6 O 0.6848(7) 0.1971(7) 0.8218(7) 0.158(4) Uani 1 1 d . . . C4 C 0.8359(5) 0.9573(4) 0.5924(5) 0.0436(11) Uani 1 1 d . . . H4A H 0.8193 1.0203 0.6342 0.065 Uiso 1 1 calc R . . H4B H 0.8057 0.9655 0.4936 0.065 Uiso 1 1 calc R . . H4C H 0.9463 0.9387 0.6267 0.065 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01636(19) 0.01802(19) 0.01707(19) 0.00077(18) 0.00314(13) -0.00214(18) Cl1 0.0452(6) 0.0449(6) 0.0345(5) -0.0083(4) 0.0163(5) -0.0017(5) N1 0.0153(11) 0.0176(12) 0.0219(12) -0.0009(15) 0.0043(9) -0.0047(14) N3 0.0209(13) 0.0240(17) 0.0169(12) 0.0003(13) 0.0010(10) 0.0008(13) N2 0.0170(14) 0.0204(15) 0.0242(15) 0.0027(12) 0.0043(11) -0.0012(11) N4 0.0164(13) 0.0196(14) 0.0226(15) -0.0025(11) 0.0062(11) -0.0024(11) C16 0.0251(16) 0.0374(19) 0.0205(15) -0.003(2) 0.0002(12) 0.001(2) C12 0.0215(18) 0.0218(18) 0.038(2) -0.0017(15) 0.0095(16) -0.0018(14) C13 0.0202(16) 0.0227(18) 0.0216(17) 0.0029(13) 0.0039(13) 0.0031(13) C1 0.0209(18) 0.0231(18) 0.0270(19) -0.0013(14) 0.0035(14) -0.0088(14) C6 0.0239(19) 0.0275(19) 0.0218(18) 0.0048(14) -0.0011(14) 0.0011(14) C11 0.0200(17) 0.0192(16) 0.0255(18) 0.0006(13) 0.0093(14) -0.0006(13) C9 0.029(2) 0.034(2) 0.024(2) -0.0040(16) -0.0021(16) -0.0088(16) C10 0.032(2) 0.0243(19) 0.029(2) -0.0064(15) 0.0051(16) -0.0109(15) C2 0.0134(16) 0.0255(18) 0.033(2) 0.0054(15) 0.0036(14) -0.0046(13) C3 0.027(2) 0.032(2) 0.0254(19) 0.0084(15) 0.0093(15) 0.0019(16) C7 0.037(2) 0.051(3) 0.023(2) 0.0013(18) -0.0049(17) -0.004(2) C15 0.0264(19) 0.0267(17) 0.029(2) -0.0018(15) 0.0083(15) 0.0039(15) C8 0.024(2) 0.038(2) 0.030(2) -0.0012(17) 0.0029(15) 0.0029(17) C5 0.032(2) 0.031(2) 0.027(2) 0.0073(15) 0.0025(16) 0.0002(16) C14 0.0179(16) 0.026(2) 0.0182(15) 0.0011(12) 0.0032(12) 0.0039(12) Cl2 0.0202(4) 0.0363(5) 0.0324(5) -0.0025(4) 0.0075(3) -0.0041(4) O5 0.0224(14) 0.0445(17) 0.062(2) 0.0043(15) 0.0151(14) -0.0023(13) O1 0.062(2) 0.089(3) 0.055(2) -0.026(2) 0.0073(19) 0.007(2) O1W 0.066(2) 0.081(3) 0.043(2) -0.0138(19) 0.0115(18) 0.019(2) O4 0.062(2) 0.095(3) 0.065(3) 0.008(2) 0.044(2) 0.017(2) O2 0.096(3) 0.069(3) 0.059(3) 0.005(2) 0.024(2) 0.040(2) O3 0.059(2) 0.063(2) 0.089(3) 0.011(2) 0.031(2) -0.014(2) O7 0.048(2) 0.125(4) 0.066(3) -0.026(3) 0.012(2) 0.015(2) O8 0.048(3) 0.080(4) 0.421(14) -0.105(6) 0.086(5) -0.034(3) O6 0.084(4) 0.280(11) 0.134(5) 0.133(6) 0.069(4) 0.093(5) C4 0.040(2) 0.047(3) 0.045(3) 0.019(2) 0.014(2) -0.002(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 Ni1 N2 1.922(3) . ? Ni1 N3 1.936(3) . ? Ni1 N4 1.937(3) . ? Ni1 N1 1.941(2) . ? Cl1 O4 1.411(4) . ? Cl1 O1 1.426(4) . ? Cl1 O3 1.428(4) . ? Cl1 O2 1.452(4) . ? N1 C14 1.502(4) . ? N1 C1 1.503(5) . ? N1 H1C 0.9300 . ? N3 C9 1.483(5) . ? N3 C6 1.520(5) . ? N3 H3A 0.9300 . ? N2 C3 1.497(5) . ? N2 C2 1.498(4) . ? N2 H2C 0.9300 . ? N4 C11 1.482(4) . ? N4 C10 1.498(4) . ? N4 H4D 0.9300 . ? C16 C14 1.543(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C12 C11 1.506(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.543(5) . ? C13 C11 1.546(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C1 C2 1.494(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C6 C8 1.502(6) . ? C6 C7 1.542(5) . ? C6 C5 1.551(6) . ? C11 H11 1.0000 . ? C9 C10 1.508(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.512(6) . ? C3 C5 1.526(5) . ? C3 H3 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C15 C14 1.517(5) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? Cl2 O8 1.365(5) . ? Cl2 O6 1.399(6) . ? Cl2 O5 1.424(3) . ? Cl2 O7 1.435(5) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? 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 Ni1 N3 92.94(13) . . ? N2 Ni1 N4 179.17(13) . . ? N3 Ni1 N4 87.12(13) . . ? N2 Ni1 N1 87.74(13) . . ? N3 Ni1 N1 175.47(15) . . ? N4 Ni1 N1 92.13(13) . . ? O4 Cl1 O1 114.0(3) . . ? O4 Cl1 O3 108.0(3) . . ? O1 Cl1 O3 107.2(3) . . ? O4 Cl1 O2 111.4(3) . . ? O1 Cl1 O2 108.0(3) . . ? O3 Cl1 O2 108.0(3) . . ? C14 N1 C1 115.2(3) . . ? C14 N1 Ni1 115.75(19) . . ? C1 N1 Ni1 108.3(2) . . ? C14 N1 H1C 105.5 . . ? C1 N1 H1C 105.5 . . ? Ni1 N1 H1C 105.5 . . ? C9 N3 C6 114.7(3) . . ? C9 N3 Ni1 108.8(2) . . ? C6 N3 Ni1 115.3(2) . . ? C9 N3 H3A 105.7 . . ? C6 N3 H3A 105.7 . . ? Ni1 N3 H3A 105.7 . . ? C3 N2 C2 114.4(3) . . ? C3 N2 Ni1 113.9(2) . . ? C2 N2 Ni1 105.7(2) . . ? C3 N2 H2C 107.5 . . ? C2 N2 H2C 107.5 . . ? Ni1 N2 H2C 107.5 . . ? C11 N4 C10 114.7(3) . . ? C11 N4 Ni1 113.4(2) . . ? C10 N4 Ni1 105.9(2) . . ? C11 N4 H4D 107.5 . . ? C10 N4 H4D 107.5 . . ? Ni1 N4 H4D 107.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C11 118.1(3) . . ? C14 C13 H13A 107.8 . . ? C11 C13 H13A 107.8 . . ? C14 C13 H13B 107.8 . . ? C11 C13 H13B 107.8 . . ? H13A C13 H13B 107.1 . . ? C2 C1 N1 106.1(3) . . ? C2 C1 H1A 110.5 . . ? N1 C1 H1A 110.5 . . ? C2 C1 H1B 110.5 . . ? N1 C1 H1B 110.5 . . ? H1A C1 H1B 108.7 . . ? C8 C6 N3 108.8(3) . . ? C8 C6 C7 108.5(3) . . ? N3 C6 C7 110.9(3) . . ? C8 C6 C5 113.4(3) . . ? N3 C6 C5 106.7(3) . . ? C7 C6 C5 108.6(3) . . ? N4 C11 C12 112.8(3) . . ? N4 C11 C13 108.6(3) . . ? C12 C11 C13 111.0(3) . . ? N4 C11 H11 108.1 . . ? C12 C11 H11 108.1 . . ? C13 C11 H11 108.1 . . ? N3 C9 C10 105.9(3) . . ? N3 C9 H9A 110.5 . . ? C10 C9 H9A 110.5 . . ? N3 C9 H9B 110.5 . . ? C10 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? N4 C10 C9 105.4(3) . . ? N4 C10 H10A 110.7 . . ? C9 C10 H10A 110.7 . . ? N4 C10 H10B 110.7 . . ? C9 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? C1 C2 N2 106.5(3) . . ? C1 C2 H2A 110.4 . . ? N2 C2 H2A 110.4 . . ? C1 C2 H2B 110.4 . . ? N2 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? N2 C3 C4 113.0(3) . . ? N2 C3 C5 109.9(3) . . ? C4 C3 C5 109.9(3) . . ? N2 C3 H3 108.0 . . ? C4 C3 H3 108.0 . . ? C5 C3 H3 108.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C5 C6 118.8(3) . . ? C3 C5 H5A 107.6 . . ? C6 C5 H5A 107.6 . . ? C3 C5 H5B 107.6 . . ? C6 C5 H5B 107.6 . . ? H5A C5 H5B 107.0 . . ? N1 C14 C15 108.9(3) . . ? N1 C14 C16 110.7(3) . . ? C15 C14 C16 108.4(3) . . ? N1 C14 C13 107.2(3) . . ? C15 C14 C13 112.9(3) . . ? C16 C14 C13 108.8(3) . . ? O8 Cl2 O6 110.3(6) . . ? O8 Cl2 O5 111.2(3) . . ? O6 Cl2 O5 109.9(3) . . ? O8 Cl2 O7 106.6(5) . . ? O6 Cl2 O7 104.8(4) . . ? O5 Cl2 O7 113.8(2) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? 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 C14 138.0(3) . . . . ? N3 Ni1 N1 C14 -123.2(18) . . . . ? N4 Ni1 N1 C14 -42.8(3) . . . . ? N2 Ni1 N1 C1 7.0(2) . . . . ? N3 Ni1 N1 C1 106(2) . . . . ? N4 Ni1 N1 C1 -173.9(2) . . . . ? N2 Ni1 N3 C9 -172.2(3) . . . . ? N4 Ni1 N3 C9 8.6(3) . . . . ? N1 Ni1 N3 C9 89.2(19) . . . . ? N2 Ni1 N3 C6 -41.7(3) . . . . ? N4 Ni1 N3 C6 139.1(3) . . . . ? N1 Ni1 N3 C6 -140.3(18) . . . . ? N3 Ni1 N2 C3 -26.7(3) . . . . ? N4 Ni1 N2 C3 68(9) . . . . ? N1 Ni1 N2 C3 148.8(2) . . . . ? N3 Ni1 N2 C2 -153.2(2) . . . . ? N4 Ni1 N2 C2 -59(9) . . . . ? N1 Ni1 N2 C2 22.3(2) . . . . ? N2 Ni1 N4 C11 54(9) . . . . ? N3 Ni1 N4 C11 148.6(2) . . . . ? N1 Ni1 N4 C11 -27.0(2) . . . . ? N2 Ni1 N4 C10 -73(9) . . . . ? N3 Ni1 N4 C10 21.9(2) . . . . ? N1 Ni1 N4 C10 -153.6(2) . . . . ? C14 N1 C1 C2 -166.2(3) . . . . ? Ni1 N1 C1 C2 -34.8(3) . . . . ? C9 N3 C6 C8 74.4(4) . . . . ? Ni1 N3 C6 C8 -53.3(3) . . . . ? C9 N3 C6 C7 -44.9(5) . . . . ? Ni1 N3 C6 C7 -172.5(3) . . . . ? C9 N3 C6 C5 -162.9(3) . . . . ? Ni1 N3 C6 C5 69.5(3) . . . . ? C10 N4 C11 C12 -42.5(4) . . . . ? Ni1 N4 C11 C12 -164.4(2) . . . . ? C10 N4 C11 C13 -166.0(3) . . . . ? Ni1 N4 C11 C13 72.2(3) . . . . ? C14 C13 C11 N4 -48.7(4) . . . . ? C14 C13 C11 C12 -173.2(3) . . . . ? C6 N3 C9 C10 -167.9(3) . . . . ? Ni1 N3 C9 C10 -37.0(4) . . . . ? C11 N4 C10 C9 -173.2(3) . . . . ? Ni1 N4 C10 C9 -47.3(3) . . . . ? N3 C9 C10 N4 55.3(4) . . . . ? N1 C1 C2 N2 54.0(4) . . . . ? C3 N2 C2 C1 -173.6(3) . . . . ? Ni1 N2 C2 C1 -47.4(3) . . . . ? C2 N2 C3 C4 -44.8(4) . . . . ? Ni1 N2 C3 C4 -166.6(3) . . . . ? C2 N2 C3 C5 -167.9(3) . . . . ? Ni1 N2 C3 C5 70.3(3) . . . . ? N2 C3 C5 C6 -44.7(5) . . . . ? C4 C3 C5 C6 -169.5(4) . . . . ? C8 C6 C5 C3 95.0(4) . . . . ? N3 C6 C5 C3 -24.8(5) . . . . ? C7 C6 C5 C3 -144.3(4) . . . . ? C1 N1 C14 C15 74.5(3) . . . . ? Ni1 N1 C14 C15 -53.2(4) . . . . ? C1 N1 C14 C16 -44.6(4) . . . . ? Ni1 N1 C14 C16 -172.3(3) . . . . ? C1 N1 C14 C13 -163.1(3) . . . . ? Ni1 N1 C14 C13 69.2(3) . . . . ? C11 C13 C14 N1 -21.8(4) . . . . ? C11 C13 C14 C15 98.1(4) . . . . ? C11 C13 C14 C16 -141.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.07 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.832 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.085 data_delta-3 _database_code_depnum_ccdc_archive 'CCDC 726190' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H49 Cl2 N5 Ni O10' _chemical_formula_weight 673.27 _chemical_absolute_configuration rmad 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 Tetragonal _symmetry_space_group_name_H-M P4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 13.4764(10) _cell_length_b 13.4764(10) _cell_length_c 17.411(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3162.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2854 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 24.09 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.839 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7521 _exptl_absorpt_correction_T_max 0.8988 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13849 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0926 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.06 _reflns_number_total 4735 _reflns_number_gt 3045 _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^)+(0.0574P)^2^+1.7755P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 4735 _refine_ls_number_parameters 362 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.1053 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.88110(5) 0.37128(5) 0.22791(4) 0.02293(19) Uani 1 1 d . . . Cl2 Cl 0.62394(13) 0.34576(13) 0.57824(11) 0.0393(4) Uani 1 1 d . . . N1 N 0.8823(4) 0.3640(4) 0.3496(3) 0.0284(15) Uani 1 1 d . . . H1C H 0.9059 0.4254 0.3656 0.034 Uiso 1 1 calc R . . N3 N 0.8677(4) 0.3705(4) 0.1065(3) 0.0263(14) Uani 1 1 d . . . H3A H 0.9311 0.3828 0.0875 0.032 Uiso 1 1 calc R . . O1 O 0.9436(3) 0.5164(3) 0.2398(3) 0.0309(11) Uani 1 1 d . . . O2 O 1.0397(3) 0.3906(3) 0.2087(2) 0.0286(10) Uani 1 1 d . . . N4 N 0.8861(4) 0.2175(3) 0.2190(3) 0.0267(12) Uani 1 1 d . . . H4D H 0.8235 0.1921 0.2297 0.032 Uiso 1 1 calc R . . N2 N 0.7300(4) 0.4008(4) 0.2402(3) 0.0286(12) Uani 1 1 d . . . H2C H 0.6962 0.3412 0.2338 0.034 Uiso 1 1 calc R . . C17 C 1.0275(4) 0.4805(4) 0.2236(4) 0.0263(13) Uani 1 1 d . . . C19 C 1.0964(5) 0.6500(5) 0.1875(4) 0.0350(17) Uani 1 1 d . . . H19A H 1.1597 0.6797 0.1702 0.042 Uiso 1 1 calc R . . H19B H 1.0544 0.6397 0.1415 0.042 Uiso 1 1 calc R . . C18 C 1.1181(4) 0.5493(4) 0.2239(4) 0.0270(13) Uani 1 1 d . . . H18 H 1.1384 0.5606 0.2785 0.032 Uiso 1 1 calc R . . N5 N 1.1998(4) 0.4967(4) 0.1842(3) 0.0367(14) Uani 1 1 d . . . H5A H 1.1839 0.4885 0.1338 0.055 Uiso 1 1 calc R . . H5B H 1.2091 0.4362 0.2064 0.055 Uiso 1 1 calc R . . H5C H 1.2566 0.5329 0.1880 0.055 Uiso 1 1 calc R . . C1 C 0.7771(5) 0.3626(5) 0.3721(4) 0.0387(18) Uani 1 1 d . . . H1A H 0.7704 0.3843 0.4262 0.046 Uiso 1 1 calc R . . H1B H 0.7507 0.2943 0.3678 0.046 Uiso 1 1 calc R . . C3 C 0.6841(5) 0.4749(5) 0.1878(4) 0.0324(16) Uani 1 1 d . . . H3 H 0.7178 0.5401 0.1959 0.039 Uiso 1 1 calc R . . C6 C 0.8002(5) 0.4434(6) 0.0671(4) 0.0392(18) Uani 1 1 d . . . C5 C 0.6988(5) 0.4438(5) 0.1029(4) 0.0351(17) Uani 1 1 d . . . H5D H 0.6716 0.3759 0.0975 0.042 Uiso 1 1 calc R . . H5E H 0.6566 0.4879 0.0713 0.042 Uiso 1 1 calc R . . C10 C 0.9090(5) 0.1998(5) 0.1364(4) 0.0360(17) Uani 1 1 d . . . H10A H 0.8959 0.1295 0.1234 0.043 Uiso 1 1 calc R . . H10B H 0.9800 0.2137 0.1265 0.043 Uiso 1 1 calc R . . C2 C 0.7198(5) 0.4301(5) 0.3214(4) 0.0388(18) Uani 1 1 d . . . H2A H 0.6488 0.4284 0.3362 0.047 Uiso 1 1 calc R . . H2B H 0.7439 0.4990 0.3280 0.047 Uiso 1 1 calc R . . C9 C 0.8454(6) 0.2663(5) 0.0872(4) 0.0371(17) Uani 1 1 d . . . H9A H 0.8595 0.2540 0.0322 0.045 Uiso 1 1 calc R . . H9B H 0.7744 0.2523 0.0967 0.045 Uiso 1 1 calc R . . C15 C 0.9211(6) 0.2821(6) 0.4755(4) 0.0453(18) Uani 1 1 d . . . H15A H 0.9212 0.3489 0.4978 0.068 Uiso 1 1 calc R . . H15B H 0.9705 0.2409 0.5018 0.068 Uiso 1 1 calc R . . H15C H 0.8552 0.2523 0.4818 0.068 Uiso 1 1 calc R . . C13 C 0.9295(5) 0.1856(5) 0.3542(4) 0.0330(16) Uani 1 1 d . . . H13A H 0.9663 0.1363 0.3852 0.040 Uiso 1 1 calc R . . H13B H 0.8581 0.1695 0.3591 0.040 Uiso 1 1 calc R . . C16 C 1.0544(5) 0.3210(5) 0.3838(4) 0.0409(18) Uani 1 1 d . . . H16A H 1.0611 0.3896 0.4019 0.061 Uiso 1 1 calc R . . H16B H 1.0751 0.3170 0.3299 0.061 Uiso 1 1 calc R . . H16C H 1.0964 0.2775 0.4150 0.061 Uiso 1 1 calc R . . C8 C 0.8486(5) 0.5455(5) 0.0737(5) 0.0460(19) Uani 1 1 d . . . H8A H 0.8605 0.5609 0.1279 0.069 Uiso 1 1 calc R . . H8B H 0.8045 0.5957 0.0515 0.069 Uiso 1 1 calc R . . H8C H 0.9118 0.5454 0.0458 0.069 Uiso 1 1 calc R . . C12 C 0.9683(6) 0.0579(5) 0.2563(4) 0.043(2) Uani 1 1 d . . . H12A H 0.9039 0.0259 0.2646 0.064 Uiso 1 1 calc R . . H12B H 1.0172 0.0298 0.2919 0.064 Uiso 1 1 calc R . . H12C H 0.9901 0.0464 0.2034 0.064 Uiso 1 1 calc R . . C4 C 0.5748(5) 0.4883(6) 0.2031(5) 0.0438(19) Uani 1 1 d . . . H4A H 0.5417 0.4236 0.2017 0.066 Uiso 1 1 calc R . . H4B H 0.5461 0.5317 0.1638 0.066 Uiso 1 1 calc R . . H4C H 0.5656 0.5184 0.2538 0.066 Uiso 1 1 calc R . . C14 C 0.9462(5) 0.2884(5) 0.3910(4) 0.0329(16) Uani 1 1 d . . . C7 C 0.7894(5) 0.4186(6) -0.0191(5) 0.051(2) Uani 1 1 d . . . H7A H 0.7536 0.4723 -0.0450 0.077 Uiso 1 1 calc R . . H7B H 0.7525 0.3564 -0.0249 0.077 Uiso 1 1 calc R . . H7C H 0.8554 0.4113 -0.0421 0.077 Uiso 1 1 calc R . . C11 C 0.9586(5) 0.1707(5) 0.2707(4) 0.0303(16) Uani 1 1 d . . . H11 H 1.0248 0.2023 0.2621 0.036 Uiso 1 1 calc R . . O7 O 0.5202(4) 0.3489(4) 0.5640(3) 0.0581(16) Uani 1 1 d . . . O8 O 0.6656(4) 0.2666(4) 0.5334(3) 0.0559(15) Uani 1 1 d . . . O9 O 0.6424(4) 0.3301(5) 0.6572(3) 0.0699(18) Uani 1 1 d . . . O10 O 0.6705(5) 0.4359(4) 0.5570(4) 0.0690(19) Uani 1 1 d . . . C20 C 1.0447(6) 0.7227(5) 0.2406(5) 0.050(2) Uani 1 1 d . . . H20 H 0.9915 0.6859 0.2688 0.060 Uiso 1 1 calc R . . C22 C 0.9949(8) 0.8040(7) 0.1925(7) 0.089(4) Uani 1 1 d . . . H22A H 0.9449 0.7742 0.1588 0.134 Uiso 1 1 calc R . . H22B H 1.0451 0.8379 0.1613 0.134 Uiso 1 1 calc R . . H22C H 0.9629 0.8521 0.2268 0.134 Uiso 1 1 calc R . . C21 C 1.1139(9) 0.7677(7) 0.2994(6) 0.090(4) Uani 1 1 d . . . H21A H 1.1631 0.8093 0.2734 0.135 Uiso 1 1 calc R . . H21B H 1.1478 0.7146 0.3276 0.135 Uiso 1 1 calc R . . H21C H 1.0756 0.8083 0.3355 0.135 Uiso 1 1 calc R . . Cl1 Cl 0.61812(13) 0.11320(12) 0.23180(13) 0.0401(4) Uiso 0.447(12) 1 d PD A 1 O5 O 0.6986(8) 0.0437(9) 0.2279(9) 0.062(4) Uiso 0.447(12) 1 d PD A 1 O3 O 0.5352(8) 0.0665(11) 0.2675(9) 0.079(6) Uiso 0.447(12) 1 d PD A 1 O4 O 0.6036(12) 0.1614(12) 0.1612(7) 0.098(6) Uiso 0.447(12) 1 d PD A 1 O6 O 0.6517(9) 0.1888(8) 0.2871(7) 0.072(5) Uiso 0.447(12) 1 d PD A 1 Cl1' Cl 0.61812(13) 0.11320(12) 0.23180(13) 0.0401(4) Uiso 0.553(12) 1 d PD A 2 O5' O 0.7071(6) 0.0682(7) 0.2557(6) 0.048(3) Uiso 0.553(12) 1 d PD A 2 O3' O 0.5405(7) 0.1053(9) 0.2884(6) 0.061(4) Uiso 0.553(12) 1 d PD A 2 O6' O 0.5760(8) 0.0510(8) 0.1686(6) 0.074(4) Uiso 0.553(12) 1 d PD A 2 O4' O 0.6283(8) 0.2067(6) 0.1965(6) 0.064(4) Uiso 0.553(12) 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 Ni1 0.0248(4) 0.0216(4) 0.0224(4) -0.0009(4) 0.0021(4) -0.0008(4) Cl2 0.0358(10) 0.0435(11) 0.0386(10) -0.0035(8) 0.0002(8) -0.0037(8) N1 0.034(3) 0.028(3) 0.023(3) -0.002(2) 0.000(2) 0.002(2) N3 0.026(3) 0.034(3) 0.018(3) 0.005(2) 0.005(2) -0.002(2) O1 0.028(3) 0.021(2) 0.043(3) 0.000(2) 0.001(2) -0.0002(19) O2 0.029(2) 0.026(2) 0.031(3) 0.0019(19) 0.0002(19) -0.0027(19) N4 0.027(3) 0.023(3) 0.030(3) 0.001(2) 0.004(3) -0.002(2) N2 0.030(3) 0.026(3) 0.030(3) 0.000(2) 0.005(3) -0.004(2) C17 0.034(4) 0.023(3) 0.022(3) 0.005(3) -0.009(3) 0.000(3) C19 0.032(4) 0.033(4) 0.040(4) 0.010(3) 0.005(3) -0.008(3) C18 0.030(3) 0.021(3) 0.030(3) 0.001(3) -0.001(3) -0.001(3) N5 0.029(3) 0.040(4) 0.041(4) 0.007(3) -0.003(3) 0.000(3) C1 0.053(5) 0.043(4) 0.020(3) 0.001(3) 0.011(3) 0.015(4) C3 0.036(4) 0.027(4) 0.034(4) -0.001(3) -0.001(3) -0.001(3) C6 0.033(4) 0.054(5) 0.031(4) 0.007(4) 0.000(3) 0.006(3) C5 0.035(4) 0.041(4) 0.029(4) 0.000(3) -0.004(3) 0.008(3) C10 0.041(4) 0.036(4) 0.031(4) -0.012(3) 0.001(3) 0.005(3) C2 0.036(4) 0.046(5) 0.034(4) 0.002(3) 0.008(3) 0.011(3) C9 0.055(5) 0.035(4) 0.022(3) -0.005(3) -0.002(3) -0.003(3) C15 0.059(5) 0.055(5) 0.021(4) 0.002(4) 0.007(4) 0.004(4) C13 0.044(4) 0.022(4) 0.032(4) 0.008(3) 0.007(3) 0.002(3) C16 0.050(5) 0.038(4) 0.035(4) 0.002(3) -0.008(4) 0.004(4) C8 0.041(4) 0.043(4) 0.054(5) 0.021(4) -0.010(4) 0.004(4) C12 0.055(5) 0.026(4) 0.047(5) -0.004(3) 0.015(4) 0.000(3) C4 0.032(4) 0.054(5) 0.046(5) -0.005(4) -0.001(3) 0.007(4) C14 0.043(4) 0.034(4) 0.022(3) 0.007(3) -0.001(3) 0.002(3) C7 0.049(4) 0.074(5) 0.030(4) 0.005(4) -0.012(4) 0.005(4) C11 0.031(4) 0.027(4) 0.033(4) 0.002(3) 0.005(3) 0.008(3) O7 0.033(3) 0.077(4) 0.064(4) -0.025(3) -0.004(3) 0.001(3) O8 0.044(3) 0.057(4) 0.067(4) -0.014(3) 0.002(3) -0.003(3) O9 0.059(4) 0.113(6) 0.038(3) 0.008(3) 0.000(3) -0.006(3) O10 0.084(4) 0.041(3) 0.081(5) -0.001(3) -0.021(4) -0.024(3) C20 0.077(6) 0.026(4) 0.045(5) -0.005(4) 0.020(4) -0.010(4) C22 0.106(9) 0.044(6) 0.118(10) -0.011(6) 0.002(8) 0.025(6) C21 0.155(11) 0.054(6) 0.062(7) -0.019(5) -0.011(7) -0.024(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 Ni1 N4 2.079(5) . ? Ni1 N2 2.086(5) . ? Ni1 N3 2.121(6) . ? Ni1 N1 2.121(6) . ? Ni1 O1 2.139(4) . ? Ni1 O2 2.178(4) . ? Cl2 O9 1.413(6) . ? Cl2 O10 1.417(6) . ? Cl2 O7 1.420(5) . ? Cl2 O8 1.436(5) . ? N1 C1 1.470(8) . ? N1 C14 1.516(8) . ? N3 C9 1.475(8) . ? N3 C6 1.505(9) . ? O1 C17 1.261(7) . ? O2 C17 1.251(7) . ? N4 C11 1.471(8) . ? N4 C10 1.489(9) . ? N2 C2 1.474(9) . ? N2 C3 1.488(8) . ? C17 C18 1.533(8) . ? C19 C20 1.516(10) . ? C19 C18 1.525(8) . ? C18 N5 1.482(8) . ? C1 C2 1.485(9) . ? C3 C4 1.507(9) . ? C3 C5 1.549(9) . ? C6 C5 1.502(9) . ? C6 C8 1.526(10) . ? C6 C7 1.544(11) . ? C10 C9 1.507(10) . ? C15 C14 1.513(10) . ? C13 C11 1.519(9) . ? C13 C14 1.542(9) . ? C16 C14 1.529(10) . ? C12 C11 1.547(9) . ? C20 C21 1.512(12) . ? C20 C22 1.534(13) . ? Cl1 O4 1.403(8) . ? Cl1 O3 1.425(8) . ? Cl1 O5 1.434(7) . ? Cl1 O6 1.473(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 N4 Ni1 N2 103.27(19) . . ? N4 Ni1 N3 85.6(2) . . ? N2 Ni1 N3 91.2(2) . . ? N4 Ni1 N1 91.6(2) . . ? N2 Ni1 N1 85.0(2) . . ? N3 Ni1 N1 174.67(18) . . ? N4 Ni1 O1 154.86(17) . . ? N2 Ni1 O1 101.56(18) . . ? N3 Ni1 O1 97.7(2) . . ? N1 Ni1 O1 86.7(2) . . ? N4 Ni1 O2 94.33(18) . . ? N2 Ni1 O2 161.92(18) . . ? N3 Ni1 O2 86.02(19) . . ? N1 Ni1 O2 98.74(18) . . ? O1 Ni1 O2 61.27(15) . . ? O9 Cl2 O10 107.8(4) . . ? O9 Cl2 O7 110.3(4) . . ? O10 Cl2 O7 111.4(4) . . ? O9 Cl2 O8 110.4(4) . . ? O10 Cl2 O8 108.8(4) . . ? O7 Cl2 O8 108.2(3) . . ? C1 N1 C14 114.4(5) . . ? C1 N1 Ni1 105.0(4) . . ? C14 N1 Ni1 120.7(4) . . ? C9 N3 C6 113.2(5) . . ? C9 N3 Ni1 104.4(4) . . ? C6 N3 Ni1 120.2(4) . . ? C17 O1 Ni1 88.9(3) . . ? C17 O2 Ni1 87.5(3) . . ? C11 N4 C10 112.7(5) . . ? C11 N4 Ni1 113.8(4) . . ? C10 N4 Ni1 103.8(4) . . ? C2 N2 C3 111.7(5) . . ? C2 N2 Ni1 103.9(4) . . ? C3 N2 Ni1 118.1(4) . . ? O2 C17 O1 122.3(5) . . ? O2 C17 C18 118.9(5) . . ? O1 C17 C18 118.8(5) . . ? C20 C19 C18 114.2(6) . . ? N5 C18 C19 112.0(5) . . ? N5 C18 C17 107.5(5) . . ? C19 C18 C17 112.6(5) . . ? N1 C1 C2 109.6(6) . . ? N2 C3 C4 112.2(6) . . ? N2 C3 C5 110.5(5) . . ? C4 C3 C5 109.1(6) . . ? C5 C6 N3 111.2(6) . . ? C5 C6 C8 110.7(6) . . ? N3 C6 C8 107.2(6) . . ? C5 C6 C7 108.6(6) . . ? N3 C6 C7 111.0(6) . . ? C8 C6 C7 108.0(6) . . ? C6 C5 C3 120.9(6) . . ? N4 C10 C9 109.6(5) . . ? N2 C2 C1 110.9(5) . . ? N3 C9 C10 108.7(5) . . ? C11 C13 C14 118.5(5) . . ? C15 C14 N1 111.9(6) . . ? C15 C14 C16 108.0(6) . . ? N1 C14 C16 108.0(5) . . ? C15 C14 C13 108.7(6) . . ? N1 C14 C13 108.9(5) . . ? C16 C14 C13 111.3(6) . . ? N4 C11 C13 111.0(5) . . ? N4 C11 C12 112.2(6) . . ? C13 C11 C12 107.9(5) . . ? C21 C20 C19 112.9(8) . . ? C21 C20 C22 110.6(7) . . ? C19 C20 C22 109.3(7) . . ? O4 Cl1 O3 118.5(9) . . ? O4 Cl1 O5 111.4(8) . . ? O3 Cl1 O5 109.0(8) . . ? O4 Cl1 O6 107.2(8) . . ? O3 Cl1 O6 105.1(8) . . ? O5 Cl1 O6 104.5(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 N4 Ni1 N1 C1 -91.9(4) . . . . ? N2 Ni1 N1 C1 11.3(4) . . . . ? N3 Ni1 N1 C1 -34(2) . . . . ? O1 Ni1 N1 C1 113.2(4) . . . . ? O2 Ni1 N1 C1 173.5(4) . . . . ? N4 Ni1 N1 C14 39.1(5) . . . . ? N2 Ni1 N1 C14 142.3(5) . . . . ? N3 Ni1 N1 C14 97(2) . . . . ? O1 Ni1 N1 C14 -115.8(5) . . . . ? O2 Ni1 N1 C14 -55.5(5) . . . . ? N4 Ni1 N3 C9 13.2(4) . . . . ? N2 Ni1 N3 C9 -90.0(4) . . . . ? N1 Ni1 N3 C9 -45(2) . . . . ? O1 Ni1 N3 C9 168.1(4) . . . . ? O2 Ni1 N3 C9 107.8(4) . . . . ? N4 Ni1 N3 C6 141.5(5) . . . . ? N2 Ni1 N3 C6 38.3(5) . . . . ? N1 Ni1 N3 C6 83(2) . . . . ? O1 Ni1 N3 C6 -63.5(5) . . . . ? O2 Ni1 N3 C6 -123.8(5) . . . . ? N4 Ni1 O1 C17 14.7(7) . . . . ? N2 Ni1 O1 C17 -174.3(4) . . . . ? N3 Ni1 O1 C17 -81.5(4) . . . . ? N1 Ni1 O1 C17 101.5(4) . . . . ? O2 Ni1 O1 C17 -0.4(3) . . . . ? N4 Ni1 O2 C17 -173.3(4) . . . . ? N2 Ni1 O2 C17 19.9(8) . . . . ? N3 Ni1 O2 C17 101.4(4) . . . . ? N1 Ni1 O2 C17 -81.0(4) . . . . ? O1 Ni1 O2 C17 0.4(4) . . . . ? N2 Ni1 N4 C11 -130.2(4) . . . . ? N3 Ni1 N4 C11 139.7(4) . . . . ? N1 Ni1 N4 C11 -44.9(4) . . . . ? O1 Ni1 N4 C11 40.8(7) . . . . ? O2 Ni1 N4 C11 54.0(4) . . . . ? N2 Ni1 N4 C10 107.0(4) . . . . ? N3 Ni1 N4 C10 16.9(4) . . . . ? N1 Ni1 N4 C10 -167.7(4) . . . . ? O1 Ni1 N4 C10 -82.0(6) . . . . ? O2 Ni1 N4 C10 -68.8(4) . . . . ? N4 Ni1 N2 C2 107.7(4) . . . . ? N3 Ni1 N2 C2 -166.6(4) . . . . ? N1 Ni1 N2 C2 17.2(4) . . . . ? O1 Ni1 N2 C2 -68.4(4) . . . . ? O2 Ni1 N2 C2 -85.8(7) . . . . ? N4 Ni1 N2 C3 -128.0(4) . . . . ? N3 Ni1 N2 C3 -42.2(5) . . . . ? N1 Ni1 N2 C3 141.5(5) . . . . ? O1 Ni1 N2 C3 55.9(5) . . . . ? O2 Ni1 N2 C3 38.5(9) . . . . ? Ni1 O2 C17 O1 -0.7(6) . . . . ? Ni1 O2 C17 C18 178.0(5) . . . . ? Ni1 O1 C17 O2 0.7(6) . . . . ? Ni1 O1 C17 C18 -178.0(5) . . . . ? C20 C19 C18 N5 -157.6(6) . . . . ? C20 C19 C18 C17 81.1(8) . . . . ? O2 C17 C18 N5 15.7(8) . . . . ? O1 C17 C18 N5 -165.6(6) . . . . ? O2 C17 C18 C19 139.5(6) . . . . ? O1 C17 C18 C19 -41.7(8) . . . . ? C14 N1 C1 C2 -172.9(6) . . . . ? Ni1 N1 C1 C2 -38.3(6) . . . . ? C2 N2 C3 C4 -59.8(7) . . . . ? Ni1 N2 C3 C4 179.8(5) . . . . ? C2 N2 C3 C5 178.2(5) . . . . ? Ni1 N2 C3 C5 57.8(6) . . . . ? C9 N3 C6 C5 74.4(7) . . . . ? Ni1 N3 C6 C5 -49.9(7) . . . . ? C9 N3 C6 C8 -164.4(6) . . . . ? Ni1 N3 C6 C8 71.3(7) . . . . ? C9 N3 C6 C7 -46.7(8) . . . . ? Ni1 N3 C6 C7 -170.9(4) . . . . ? N3 C6 C5 C3 62.6(8) . . . . ? C8 C6 C5 C3 -56.5(8) . . . . ? C7 C6 C5 C3 -174.9(6) . . . . ? N2 C3 C5 C6 -67.6(8) . . . . ? C4 C3 C5 C6 168.5(6) . . . . ? C11 N4 C10 C9 -168.3(5) . . . . ? Ni1 N4 C10 C9 -44.8(6) . . . . ? C3 N2 C2 C1 -172.6(6) . . . . ? Ni1 N2 C2 C1 -44.2(7) . . . . ? N1 C1 C2 N2 58.3(8) . . . . ? C6 N3 C9 C10 -173.5(6) . . . . ? Ni1 N3 C9 C10 -41.0(6) . . . . ? N4 C10 C9 N3 60.6(7) . . . . ? C1 N1 C14 C15 -41.9(8) . . . . ? Ni1 N1 C14 C15 -168.7(5) . . . . ? C1 N1 C14 C16 -160.6(6) . . . . ? Ni1 N1 C14 C16 72.5(6) . . . . ? C1 N1 C14 C13 78.3(7) . . . . ? Ni1 N1 C14 C13 -48.6(6) . . . . ? C11 C13 C14 C15 -174.6(6) . . . . ? C11 C13 C14 N1 63.3(8) . . . . ? C11 C13 C14 C16 -55.7(8) . . . . ? C10 N4 C11 C13 -176.8(5) . . . . ? Ni1 N4 C11 C13 65.4(6) . . . . ? C10 N4 C11 C12 -56.0(7) . . . . ? Ni1 N4 C11 C12 -173.8(4) . . . . ? C14 C13 C11 N4 -75.5(8) . . . . ? C14 C13 C11 C12 161.2(6) . . . . ? C18 C19 C20 C21 76.1(8) . . . . ? C18 C19 C20 C22 -160.4(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5B O8 0.91 2.07 2.929(8) 157.0 4_664 N5 H5C O10 0.91 2.52 2.964(8) 110.6 2_764 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.587 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.087 data_lambda-3 _database_code_depnum_ccdc_archive 'CCDC 726191' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H49 Cl2 N5 Ni O10' _chemical_formula_weight 673.27 _chemical_absolute_configuration rmad 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 Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 13.4869(8) _cell_length_b 13.4869(8) _cell_length_c 17.414(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3167.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5525 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 25.47 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.838 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7581 _exptl_absorpt_correction_T_max 0.8847 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14730 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.07 _reflns_number_total 5979 _reflns_number_gt 4683 _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^)+(0.0538P)^2^+0.4906P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.010(15) _refine_ls_number_reflns 5979 _refine_ls_number_parameters 366 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.060 _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 Ni1 Ni 0.62875(3) 0.11884(3) 0.01784(2) 0.02226(12) Uani 1 1 d . . . N3 N 0.6359(2) 0.1166(2) 0.1400(2) 0.0273(9) Uani 1 1 d . . . H3A H 0.5745 0.0930 0.1560 0.033 Uiso 1 1 calc R . . N1 N 0.6294(2) 0.1325(3) -0.1032(2) 0.0285(9) Uani 1 1 d . . . H1C H 0.6168 0.0692 -0.1220 0.034 Uiso 1 1 calc R . . N4 N 0.5982(2) 0.2691(2) 0.03063(19) 0.0276(7) Uani 1 1 d . . . H4D H 0.6578 0.3027 0.0241 0.033 Uiso 1 1 calc R . . N2 N 0.7828(2) 0.1139(2) 0.00884(19) 0.0267(7) Uani 1 1 d . . . H2C H 0.8079 0.1766 0.0196 0.032 Uiso 1 1 calc R . . C19 C 0.3506(3) -0.0972(3) -0.0223(2) 0.0333(10) Uani 1 1 d . . . H19A H 0.3212 -0.1611 -0.0385 0.040 Uiso 1 1 calc R . . H19B H 0.3607 -0.0566 -0.0690 0.040 Uiso 1 1 calc R . . C17 C 0.5196(3) -0.0281(3) 0.0141(2) 0.0253(8) Uani 1 1 d . . . N5 N 0.5038(3) -0.1999(2) -0.0261(2) 0.0356(9) Uani 1 1 d . . . H5A H 0.4648 -0.2550 -0.0261 0.053 Uiso 1 1 calc R . . H5B H 0.5617 -0.2133 -0.0014 0.053 Uiso 1 1 calc R . . H5C H 0.5169 -0.1816 -0.0754 0.053 Uiso 1 1 calc R . . C18 C 0.4513(3) -0.1175(3) 0.0141(2) 0.0289(8) Uani 1 1 d . . . H18 H 0.4402 -0.1380 0.0686 0.035 Uiso 1 1 calc R . . C2 C 0.8008(3) 0.0917(3) -0.0735(2) 0.0356(10) Uani 1 1 d . . . H2A H 0.7882 0.0205 -0.0834 0.043 Uiso 1 1 calc R . . H2B H 0.8709 0.1059 -0.0864 0.043 Uiso 1 1 calc R . . C14 C 0.5554(4) 0.2001(3) -0.1431(2) 0.0371(10) Uani 1 1 d . . . C5 C 0.8140(3) 0.0695(3) 0.1447(2) 0.0328(10) Uani 1 1 d . . . H5D H 0.8305 0.1406 0.1502 0.039 Uiso 1 1 calc R . . H5E H 0.8629 0.0320 0.1756 0.039 Uiso 1 1 calc R . . C11 C 0.5254(3) 0.3150(3) -0.0227(2) 0.0319(9) Uani 1 1 d . . . H11 H 0.4602 0.2810 -0.0153 0.038 Uiso 1 1 calc R . . C1 C 0.7338(3) 0.1537(3) -0.1229(3) 0.0354(10) Uani 1 1 d . . . H1A H 0.7480 0.2249 -0.1145 0.042 Uiso 1 1 calc R . . H1B H 0.7457 0.1384 -0.1777 0.042 Uiso 1 1 calc R . . C9 C 0.6376(4) 0.2232(3) 0.1623(2) 0.0403(11) Uani 1 1 d . . . H9A H 0.6163 0.2303 0.2165 0.048 Uiso 1 1 calc R . . H9B H 0.7058 0.2495 0.1577 0.048 Uiso 1 1 calc R . . C13 C 0.5565(3) 0.3015(3) -0.1065(2) 0.0350(10) Uani 1 1 d . . . H13A H 0.5133 0.3449 -0.1379 0.042 Uiso 1 1 calc R . . H13B H 0.6248 0.3277 -0.1114 0.042 Uiso 1 1 calc R . . C10 C 0.5696(4) 0.2806(3) 0.1115(3) 0.0389(11) Uani 1 1 d . . . H10A H 0.5008 0.2569 0.1187 0.047 Uiso 1 1 calc R . . H10B H 0.5720 0.3516 0.1257 0.047 Uiso 1 1 calc R . . C7 C 0.7179(3) 0.0796(4) 0.2660(3) 0.0439(11) Uani 1 1 d . . . H7A H 0.7441 0.1470 0.2715 0.066 Uiso 1 1 calc R . . H7B H 0.7621 0.0328 0.2921 0.066 Uiso 1 1 calc R . . H7C H 0.6517 0.0761 0.2890 0.066 Uiso 1 1 calc R . . C8 C 0.6787(4) -0.0542(4) 0.1741(3) 0.0417(11) Uani 1 1 d . . . H8A H 0.6117 -0.0614 0.1951 0.063 Uiso 1 1 calc R . . H8B H 0.7245 -0.0967 0.2028 0.063 Uiso 1 1 calc R . . H8C H 0.6787 -0.0738 0.1199 0.063 Uiso 1 1 calc R . . C4 C 0.9416(3) 0.0314(4) 0.0455(3) 0.0390(11) Uani 1 1 d . . . H4A H 0.9520 0.0056 -0.0065 0.058 Uiso 1 1 calc R . . H4B H 0.9708 -0.0143 0.0829 0.058 Uiso 1 1 calc R . . H4C H 0.9733 0.0965 0.0501 0.058 Uiso 1 1 calc R . . C3 C 0.8299(3) 0.0416(3) 0.0609(2) 0.0300(9) Uani 1 1 d . . . H3 H 0.7984 -0.0245 0.0519 0.036 Uiso 1 1 calc R . . C20 C 0.2770(3) -0.0440(4) 0.0300(3) 0.0508(13) Uani 1 1 d . . . H20 H 0.3136 0.0094 0.0580 0.061 Uiso 1 1 calc R . . C6 C 0.7115(3) 0.0530(3) 0.1810(2) 0.0319(9) Uani 1 1 d . . . C16 C 0.4545(4) 0.1516(4) -0.1362(3) 0.0455(12) Uani 1 1 d . . . H16A H 0.4377 0.1434 -0.0818 0.068 Uiso 1 1 calc R . . H16B H 0.4560 0.0865 -0.1612 0.068 Uiso 1 1 calc R . . H16C H 0.4046 0.1934 -0.1611 0.068 Uiso 1 1 calc R . . C15 C 0.5804(4) 0.2109(4) -0.2288(3) 0.0518(13) Uani 1 1 d . . . H15A H 0.5269 0.2468 -0.2547 0.078 Uiso 1 1 calc R . . H15B H 0.5878 0.1451 -0.2518 0.078 Uiso 1 1 calc R . . H15C H 0.6426 0.2479 -0.2344 0.078 Uiso 1 1 calc R . . C12 C 0.5108(4) 0.4246(3) -0.0072(3) 0.0452(12) Uani 1 1 d . . . H12A H 0.4838 0.4336 0.0446 0.068 Uiso 1 1 calc R . . H12B H 0.4644 0.4522 -0.0449 0.068 Uiso 1 1 calc R . . H12C H 0.5746 0.4589 -0.0112 0.068 Uiso 1 1 calc R . . C22 C 0.1960(4) 0.0049(6) -0.0177(4) 0.084(2) Uani 1 1 d . . . H22A H 0.1553 -0.0464 -0.0421 0.126 Uiso 1 1 calc R . . H22B H 0.2264 0.0465 -0.0574 0.126 Uiso 1 1 calc R . . H22C H 0.1543 0.0459 0.0156 0.126 Uiso 1 1 calc R . . C21 C 0.2322(5) -0.1140(6) 0.0898(4) 0.084(2) Uani 1 1 d . . . H21A H 0.1864 -0.0771 0.1227 0.127 Uiso 1 1 calc R . . H21B H 0.2854 -0.1424 0.1212 0.127 Uiso 1 1 calc R . . H21C H 0.1963 -0.1674 0.0637 0.127 Uiso 1 1 calc R . . Cl2 Cl 0.62401(8) 0.65411(8) 0.11804(6) 0.0377(3) Uani 1 1 d . . . O7 O 0.5199(2) 0.6510(3) 0.1034(2) 0.0573(10) Uani 1 1 d . . . O10 O 0.6702(3) 0.5632(3) 0.0966(2) 0.0662(11) Uani 1 1 d . . . O9 O 0.6430(3) 0.6707(4) 0.1975(2) 0.0683(12) Uani 1 1 d . . . O8 O 0.6659(3) 0.7333(3) 0.0729(2) 0.0535(9) Uani 1 1 d . . . O1 O 0.48414(19) 0.05574(19) 0.03000(17) 0.0294(6) Uani 1 1 d . . . O2 O 0.60982(19) -0.03997(19) -0.00133(15) 0.0282(6) Uani 1 1 d . . . Cl1 Cl 0.8933(3) 0.3828(2) 0.01691(18) 0.0319(10) Uiso 0.542(7) 1 d PD A 1 O3 O 0.8974(6) 0.4586(5) 0.0782(4) 0.061(2) Uiso 0.542(7) 1 d PD A 1 O4 O 0.9323(6) 0.2933(5) 0.0452(4) 0.053(2) Uiso 0.542(7) 1 d PD A 1 O5 O 0.7958(5) 0.3717(5) -0.0151(4) 0.066(2) Uiso 0.542(7) 1 d PD A 1 O6 O 0.9515(5) 0.4246(5) -0.0437(4) 0.065(2) Uiso 0.542(7) 1 d PD A 1 Cl1' Cl 0.8792(3) 0.3804(3) 0.0282(2) 0.0346(13) Uiso 0.458(7) 1 d PD A 2 O3' O 0.8060(6) 0.3470(6) 0.0789(5) 0.077(3) Uiso 0.458(7) 1 d PD A 2 O4' O 0.9546(6) 0.3008(6) 0.0194(6) 0.066(3) Uiso 0.458(7) 1 d PD A 2 O5' O 0.9309(8) 0.4649(6) 0.0575(6) 0.090(4) Uiso 0.458(7) 1 d PD A 2 O6' O 0.8407(8) 0.3973(8) -0.0474(4) 0.105(4) Uiso 0.458(7) 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 Ni1 0.0213(3) 0.0245(3) 0.0210(2) -0.0019(2) 0.0000(2) -0.0008(2) N3 0.0257(18) 0.036(2) 0.0205(19) -0.0013(14) -0.0006(14) 0.0012(14) N1 0.034(2) 0.0255(18) 0.026(2) -0.0047(14) -0.0009(15) -0.0005(14) N4 0.0270(17) 0.0310(18) 0.0249(18) -0.0052(15) 0.0023(14) 0.0001(14) N2 0.0230(16) 0.0279(17) 0.0294(19) -0.0022(15) 0.0032(15) -0.0017(13) C19 0.031(2) 0.038(2) 0.031(2) -0.0062(19) -0.0044(18) -0.0075(18) C17 0.0231(19) 0.030(2) 0.0230(19) 0.0087(19) -0.0058(18) -0.0040(15) N5 0.039(2) 0.0263(19) 0.042(2) 0.0019(16) -0.0090(17) 0.0001(15) C18 0.0254(19) 0.034(2) 0.027(2) -0.0008(19) -0.0049(18) -0.0044(15) C2 0.038(3) 0.038(3) 0.031(2) -0.0045(19) 0.0071(19) 0.005(2) C14 0.050(3) 0.033(2) 0.028(2) 0.0030(19) -0.009(2) 0.001(2) C5 0.030(2) 0.038(2) 0.030(2) -0.0084(18) -0.0097(18) 0.0059(18) C11 0.028(2) 0.036(2) 0.032(2) 0.0018(19) -0.0002(18) 0.0008(18) C1 0.039(2) 0.041(3) 0.026(2) 0.0014(19) 0.006(2) -0.003(2) C9 0.049(3) 0.048(3) 0.024(2) -0.010(2) 0.000(2) 0.011(2) C13 0.040(3) 0.035(2) 0.030(2) 0.0066(19) -0.0004(19) 0.0046(19) C10 0.049(3) 0.037(3) 0.031(2) -0.008(2) 0.004(2) 0.010(2) C7 0.048(3) 0.056(3) 0.027(2) -0.004(2) -0.005(2) 0.006(2) C8 0.046(3) 0.046(3) 0.033(3) 0.007(2) -0.001(2) -0.002(2) C4 0.024(2) 0.048(3) 0.046(3) -0.013(2) 0.0005(19) 0.0039(19) C3 0.024(2) 0.033(2) 0.033(2) -0.0029(19) -0.0033(17) 0.0028(17) C20 0.027(2) 0.078(4) 0.047(3) -0.017(3) 0.005(2) -0.012(2) C6 0.033(2) 0.041(3) 0.022(2) -0.0014(18) -0.0018(17) 0.0049(19) C16 0.046(3) 0.039(3) 0.052(3) 0.006(2) -0.021(2) 0.004(2) C15 0.080(4) 0.047(3) 0.028(2) 0.007(2) -0.011(3) 0.007(2) C12 0.052(3) 0.036(3) 0.048(3) 0.006(2) 0.006(2) 0.009(2) C22 0.035(3) 0.120(6) 0.097(5) -0.005(4) 0.008(3) 0.020(4) C21 0.056(4) 0.133(7) 0.064(4) 0.009(4) 0.010(3) -0.025(4) Cl2 0.0355(6) 0.0421(6) 0.0355(6) 0.0039(5) 0.0002(5) 0.0042(5) O7 0.0365(19) 0.078(3) 0.057(2) 0.0193(19) -0.0054(16) -0.0081(17) O10 0.080(3) 0.041(2) 0.078(3) 0.0018(18) -0.022(2) 0.0193(19) O9 0.057(2) 0.112(4) 0.036(2) -0.007(2) -0.0025(17) 0.012(2) O8 0.0425(19) 0.055(2) 0.063(2) 0.0130(18) 0.0014(17) 0.0022(16) O1 0.0255(14) 0.0305(16) 0.0323(17) -0.0017(12) 0.0004(12) -0.0015(11) O2 0.0242(15) 0.0296(15) 0.0309(16) 0.0005(12) -0.0023(11) -0.0006(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N4 2.079(3) . ? Ni1 N2 2.084(3) . ? Ni1 N1 2.116(4) . ? Ni1 N3 2.129(3) . ? Ni1 O1 2.138(3) . ? Ni1 O2 2.183(3) . ? Ni1 C17 2.469(4) . ? N3 C9 1.490(5) . ? N3 C6 1.512(5) . ? N1 C1 1.478(5) . ? N1 C14 1.520(5) . ? N4 C10 1.468(5) . ? N4 C11 1.488(5) . ? N2 C3 1.476(5) . ? N2 C2 1.484(5) . ? C19 C18 1.523(5) . ? C19 C20 1.527(6) . ? C17 O2 1.257(4) . ? C17 O1 1.258(4) . ? C17 C18 1.518(5) . ? N5 C18 1.492(5) . ? C2 C1 1.503(6) . ? C14 C13 1.510(6) . ? C14 C16 1.515(7) . ? C14 C15 1.536(7) . ? C5 C3 1.522(6) . ? C5 C6 1.537(6) . ? C11 C12 1.515(6) . ? C11 C13 1.529(6) . ? C9 C10 1.490(6) . ? C7 C6 1.526(6) . ? C8 C6 1.517(6) . ? C4 C3 1.536(6) . ? C20 C22 1.523(8) . ? C20 C21 1.529(8) . ? Cl2 O9 1.424(4) . ? Cl2 O10 1.425(4) . ? Cl2 O7 1.428(3) . ? Cl2 O8 1.442(3) . ? Cl1 O4 1.405(6) . ? Cl1 O6 1.431(6) . ? Cl1 O5 1.436(6) . ? Cl1 O3 1.479(6) . ? Cl1' O3' 1.400(7) . ? Cl1' O5' 1.431(6) . ? Cl1' O6' 1.433(7) . ? Cl1' O4' 1.486(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 N4 Ni1 N2 103.66(12) . . ? N4 Ni1 N1 91.31(13) . . ? N2 Ni1 N1 85.64(13) . . ? N4 Ni1 N3 85.18(13) . . ? N2 Ni1 N3 91.69(13) . . ? N1 Ni1 N3 174.97(12) . . ? N4 Ni1 O1 101.34(11) . . ? N2 Ni1 O1 154.67(11) . . ? N1 Ni1 O1 97.87(12) . . ? N3 Ni1 O1 86.37(12) . . ? N4 Ni1 O2 161.69(11) . . ? N2 Ni1 O2 94.24(11) . . ? N1 Ni1 O2 86.18(12) . . ? N3 Ni1 O2 98.27(11) . . ? O1 Ni1 O2 61.18(10) . . ? N4 Ni1 C17 131.80(12) . . ? N2 Ni1 C17 124.54(12) . . ? N1 Ni1 C17 92.62(14) . . ? N3 Ni1 C17 92.40(13) . . ? O1 Ni1 C17 30.62(10) . . ? O2 Ni1 C17 30.56(11) . . ? C9 N3 C6 114.5(3) . . ? C9 N3 Ni1 104.3(2) . . ? C6 N3 Ni1 120.7(2) . . ? C1 N1 C14 113.8(3) . . ? C1 N1 Ni1 104.6(2) . . ? C14 N1 Ni1 120.3(3) . . ? C10 N4 C11 112.4(3) . . ? C10 N4 Ni1 104.9(2) . . ? C11 N4 Ni1 118.0(2) . . ? C3 N2 C2 112.9(3) . . ? C3 N2 Ni1 113.8(2) . . ? C2 N2 Ni1 104.0(2) . . ? C18 C19 C20 114.6(4) . . ? O2 C17 O1 122.0(3) . . ? O2 C17 C18 119.1(3) . . ? O1 C17 C18 118.9(3) . . ? O2 C17 Ni1 62.00(18) . . ? O1 C17 Ni1 59.98(18) . . ? C18 C17 Ni1 178.3(3) . . ? N5 C18 C17 107.7(3) . . ? N5 C18 C19 111.2(3) . . ? C17 C18 C19 113.5(3) . . ? N2 C2 C1 110.0(3) . . ? C13 C14 C16 111.5(4) . . ? C13 C14 N1 110.1(4) . . ? C16 C14 N1 107.1(3) . . ? C13 C14 C15 108.8(4) . . ? C16 C14 C15 108.4(4) . . ? N1 C14 C15 110.9(4) . . ? C3 C5 C6 119.1(3) . . ? N4 C11 C12 112.4(4) . . ? N4 C11 C13 111.4(3) . . ? C12 C11 C13 108.8(4) . . ? N1 C1 C2 109.4(3) . . ? C10 C9 N3 109.7(4) . . ? C14 C13 C11 120.5(4) . . ? N4 C10 C9 110.7(3) . . ? N2 C3 C5 111.4(3) . . ? N2 C3 C4 112.0(3) . . ? C5 C3 C4 109.1(3) . . ? C22 C20 C19 110.1(4) . . ? C22 C20 C21 110.9(5) . . ? C19 C20 C21 111.9(5) . . ? N3 C6 C8 107.8(3) . . ? N3 C6 C7 111.3(3) . . ? C8 C6 C7 108.6(4) . . ? N3 C6 C5 109.3(3) . . ? C8 C6 C5 111.6(4) . . ? C7 C6 C5 108.3(3) . . ? O9 Cl2 O10 108.1(2) . . ? O9 Cl2 O7 110.8(2) . . ? O10 Cl2 O7 111.0(2) . . ? O9 Cl2 O8 110.1(3) . . ? O10 Cl2 O8 108.9(2) . . ? O7 Cl2 O8 108.0(2) . . ? C17 O1 Ni1 89.4(2) . . ? C17 O2 Ni1 87.4(2) . . ? O4 Cl1 O6 113.0(5) . . ? O4 Cl1 O5 112.9(5) . . ? O6 Cl1 O5 104.9(5) . . ? O4 Cl1 O3 109.1(5) . . ? O6 Cl1 O3 103.8(5) . . ? O5 Cl1 O3 112.7(5) . . ? O3' Cl1' O5' 112.0(6) . . ? O3' Cl1' O6' 112.0(6) . . ? O5' Cl1' O6' 112.2(6) . . ? O3' Cl1' O4' 108.4(5) . . ? O5' Cl1' O4' 106.2(5) . . ? O6' Cl1' O4' 105.5(6) . . ? 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 N4 Ni1 N3 C9 -11.9(3) . . . . ? N2 Ni1 N3 C9 91.7(3) . . . . ? N1 Ni1 N3 C9 33.9(16) . . . . ? O1 Ni1 N3 C9 -113.6(3) . . . . ? O2 Ni1 N3 C9 -173.8(3) . . . . ? C17 Ni1 N3 C9 -143.7(3) . . . . ? N4 Ni1 N3 C6 -142.4(3) . . . . ? N2 Ni1 N3 C6 -38.8(3) . . . . ? N1 Ni1 N3 C6 -96.5(14) . . . . ? O1 Ni1 N3 C6 115.9(3) . . . . ? O2 Ni1 N3 C6 55.7(3) . . . . ? C17 Ni1 N3 C6 85.9(3) . . . . ? N4 Ni1 N1 C1 91.1(3) . . . . ? N2 Ni1 N1 C1 -12.5(3) . . . . ? N3 Ni1 N1 C1 45.5(15) . . . . ? O1 Ni1 N1 C1 -167.2(3) . . . . ? O2 Ni1 N1 C1 -107.0(3) . . . . ? C17 Ni1 N1 C1 -136.9(3) . . . . ? N4 Ni1 N1 C14 -38.3(3) . . . . ? N2 Ni1 N1 C14 -141.9(3) . . . . ? N3 Ni1 N1 C14 -83.9(15) . . . . ? O1 Ni1 N1 C14 63.3(3) . . . . ? O2 Ni1 N1 C14 123.5(3) . . . . ? C17 Ni1 N1 C14 93.6(3) . . . . ? N2 Ni1 N4 C10 -107.1(3) . . . . ? N1 Ni1 N4 C10 167.1(3) . . . . ? N3 Ni1 N4 C10 -16.5(3) . . . . ? O1 Ni1 N4 C10 68.8(3) . . . . ? O2 Ni1 N4 C10 85.3(4) . . . . ? C17 Ni1 N4 C10 72.4(3) . . . . ? N2 Ni1 N4 C11 126.8(3) . . . . ? N1 Ni1 N4 C11 41.0(3) . . . . ? N3 Ni1 N4 C11 -142.6(3) . . . . ? O1 Ni1 N4 C11 -57.3(3) . . . . ? O2 Ni1 N4 C11 -40.8(5) . . . . ? C17 Ni1 N4 C11 -53.7(4) . . . . ? N4 Ni1 N2 C3 129.7(3) . . . . ? N1 Ni1 N2 C3 -140.0(3) . . . . ? N3 Ni1 N2 C3 44.3(3) . . . . ? O1 Ni1 N2 C3 -40.8(4) . . . . ? O2 Ni1 N2 C3 -54.1(3) . . . . ? C17 Ni1 N2 C3 -49.8(3) . . . . ? N4 Ni1 N2 C2 -107.0(2) . . . . ? N1 Ni1 N2 C2 -16.7(2) . . . . ? N3 Ni1 N2 C2 167.5(2) . . . . ? O1 Ni1 N2 C2 82.5(4) . . . . ? O2 Ni1 N2 C2 69.1(2) . . . . ? C17 Ni1 N2 C2 73.5(3) . . . . ? N4 Ni1 C17 O2 172.1(2) . . . . ? N2 Ni1 C17 O2 -8.5(3) . . . . ? N1 Ni1 C17 O2 78.0(2) . . . . ? N3 Ni1 C17 O2 -102.3(2) . . . . ? O1 Ni1 C17 O2 179.0(4) . . . . ? N4 Ni1 C17 O1 -6.9(3) . . . . ? N2 Ni1 C17 O1 172.4(2) . . . . ? N1 Ni1 C17 O1 -101.0(2) . . . . ? N3 Ni1 C17 O1 78.7(2) . . . . ? O2 Ni1 C17 O1 -179.0(4) . . . . ? N4 Ni1 C17 C18 -57(9) . . . . ? N2 Ni1 C17 C18 122(9) . . . . ? N1 Ni1 C17 C18 -152(9) . . . . ? N3 Ni1 C17 C18 28(9) . . . . ? O1 Ni1 C17 C18 -50(9) . . . . ? O2 Ni1 C17 C18 131(9) . . . . ? O2 C17 C18 N5 -15.4(5) . . . . ? O1 C17 C18 N5 165.0(3) . . . . ? Ni1 C17 C18 N5 -145(9) . . . . ? O2 C17 C18 C19 -138.9(4) . . . . ? O1 C17 C18 C19 41.6(5) . . . . ? Ni1 C17 C18 C19 91(9) . . . . ? C20 C19 C18 N5 158.4(4) . . . . ? C20 C19 C18 C17 -80.0(5) . . . . ? C3 N2 C2 C1 167.8(3) . . . . ? Ni1 N2 C2 C1 43.9(4) . . . . ? C1 N1 C14 C13 -74.8(5) . . . . ? Ni1 N1 C14 C13 50.5(4) . . . . ? C1 N1 C14 C16 163.8(4) . . . . ? Ni1 N1 C14 C16 -71.0(4) . . . . ? C1 N1 C14 C15 45.7(5) . . . . ? Ni1 N1 C14 C15 170.9(3) . . . . ? C10 N4 C11 C12 57.9(5) . . . . ? Ni1 N4 C11 C12 -179.7(3) . . . . ? C10 N4 C11 C13 -179.7(3) . . . . ? Ni1 N4 C11 C13 -57.3(4) . . . . ? C14 N1 C1 C2 173.1(4) . . . . ? Ni1 N1 C1 C2 39.8(4) . . . . ? N2 C2 C1 N1 -59.1(5) . . . . ? C6 N3 C9 C10 172.8(4) . . . . ? Ni1 N3 C9 C10 38.7(4) . . . . ? C16 C14 C13 C11 55.1(5) . . . . ? N1 C14 C13 C11 -63.6(5) . . . . ? C15 C14 C13 C11 174.7(4) . . . . ? N4 C11 C13 C14 68.6(5) . . . . ? C12 C11 C13 C14 -167.0(4) . . . . ? C11 N4 C10 C9 173.1(4) . . . . ? Ni1 N4 C10 C9 43.6(4) . . . . ? N3 C9 C10 N4 -57.9(5) . . . . ? C2 N2 C3 C5 177.3(3) . . . . ? Ni1 N2 C3 C5 -64.4(4) . . . . ? C2 N2 C3 C4 54.8(4) . . . . ? Ni1 N2 C3 C4 173.1(3) . . . . ? C6 C5 C3 N2 74.6(5) . . . . ? C6 C5 C3 C4 -161.3(4) . . . . ? C18 C19 C20 C22 159.8(4) . . . . ? C18 C19 C20 C21 -76.5(5) . . . . ? C9 N3 C6 C8 160.8(4) . . . . ? Ni1 N3 C6 C8 -73.3(4) . . . . ? C9 N3 C6 C7 41.8(5) . . . . ? Ni1 N3 C6 C7 167.8(3) . . . . ? C9 N3 C6 C5 -77.8(4) . . . . ? Ni1 N3 C6 C5 48.2(4) . . . . ? C3 C5 C6 N3 -62.7(5) . . . . ? C3 C5 C6 C8 56.4(5) . . . . ? C3 C5 C6 C7 175.9(4) . . . . ? O2 C17 O1 Ni1 -1.0(4) . . . . ? C18 C17 O1 Ni1 178.5(3) . . . . ? N4 Ni1 O1 C17 174.7(2) . . . . ? N2 Ni1 O1 C17 -14.7(4) . . . . ? N1 Ni1 O1 C17 81.8(2) . . . . ? N3 Ni1 O1 C17 -100.9(2) . . . . ? O2 Ni1 O1 C17 0.6(2) . . . . ? O1 C17 O2 Ni1 1.0(4) . . . . ? C18 C17 O2 Ni1 -178.5(3) . . . . ? N4 Ni1 O2 C17 -19.1(5) . . . . ? N2 Ni1 O2 C17 172.9(2) . . . . ? N1 Ni1 O2 C17 -101.7(2) . . . . ? N3 Ni1 O2 C17 80.6(2) . . . . ? O1 Ni1 O2 C17 -0.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A O10 0.91 2.46 2.966(5) 115.0 3_644 N5 H5B O8 0.91 2.04 2.927(5) 163.9 1_545 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.07 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.466 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.067 # start Validation Reply Form _vrf_PLAT306_S-2 ; PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O1W RESPONSE: The hydrogen atoms of water molecule were not added. ; _vrf_PLAT306_R-2 ; PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O1W RESPONSE: The hydrogen atoms of water molecule were not added. ; _vrf_PLAT761_delta-3 ; PROBLEM: CIF Contains no X-H Bonds ...................... ? RESPONSE: The positions of ClO4- are disordered. ; _vrf_PLAT762_delta-3 ; PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles .......... ? RESPONSE: The positions of ClO4- are disordered. ; _vrf_PLAT761_lambda-3 ; PROBLEM: CIF Contains no X-H Bonds ...................... ? RESPONSE: The positions of ClO4- are disordered. ; _vrf_PLAT762_lambda-3 ; PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles .......... ? RESPONSE: The positions of ClO4- are disordered. ; # end Validation Reply Form # Attachment 'CIF.cif' data_delta-1 _database_code_depnum_ccdc_archive 'CCDC 735384' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H49 Cl2 N5 Ni O10' _chemical_formula_weight 673.27 _chemical_absolute_configuration rmad 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 Tetragonal _symmetry_space_group_name_H-M P4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 13.3805(7) _cell_length_b 13.3805(7) _cell_length_c 17.6120(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3153.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6591 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 26.17 _exptl_crystal_description prism _exptl_crystal_colour violet _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.841 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7033 _exptl_absorpt_correction_T_max 0.9058 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16828 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.01 _reflns_number_total 6515 _reflns_number_gt 5125 _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^)+(0.1016P)^2^+0.2540P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(18) _refine_ls_number_reflns 6515 _refine_ls_number_parameters 350 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1616 _refine_ls_wR_factor_gt 0.1427 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.88016(4) 0.62144(4) 0.19405(3) 0.02368(15) Uani 1 1 d . . . Cl1 Cl 0.62902(10) 0.66261(11) 0.84731(8) 0.0426(3) Uani 1 1 d . . . N3 N 0.8838(3) 0.6234(3) 0.0739(3) 0.0312(10) Uani 1 1 d . . . H3A H 0.9047 0.5597 0.0598 0.037 Uiso 1 1 calc R . . O1 O 0.9388(2) 0.4681(2) 0.1897(2) 0.0312(7) Uani 1 1 d . . . N1 N 0.8655(3) 0.6272(3) 0.3144(2) 0.0291(10) Uani 1 1 d . . . H1C H 0.9284 0.6119 0.3337 0.035 Uiso 1 1 calc R . . O2 O 1.0356(2) 0.5968(2) 0.21518(19) 0.0301(7) Uani 1 1 d . . . N4 N 0.7270(3) 0.5983(3) 0.1816(2) 0.0289(9) Uani 1 1 d . . . H4D H 0.6957 0.6600 0.1861 0.035 Uiso 1 1 calc R . . N2 N 0.8937(3) 0.7768(3) 0.2000(2) 0.0282(8) Uani 1 1 d . . . H2C H 0.8322 0.8055 0.1885 0.034 Uiso 1 1 calc R . . C5 C 0.9405(4) 0.8014(4) 0.0651(3) 0.0347(11) Uani 1 1 d . . . H5A H 0.9813 0.8469 0.0334 0.042 Uiso 1 1 calc R . . H5B H 0.8699 0.8224 0.0594 0.042 Uiso 1 1 calc R . . C18 C 1.1084(4) 0.4338(4) 0.2259(3) 0.0318(10) Uani 1 1 d . . . H18 H 1.0906 0.3946 0.2723 0.038 Uiso 1 1 calc R . . C17 C 1.0219(3) 0.5037(3) 0.2082(3) 0.0266(10) Uani 1 1 d . . . C19 C 1.1345(4) 0.3598(4) 0.1627(3) 0.0396(12) Uani 1 1 d . . . H19A H 1.1408 0.3975 0.1146 0.047 Uiso 1 1 calc R . . H19B H 1.2008 0.3306 0.1741 0.047 Uiso 1 1 calc R . . C1 C 0.8499(4) 0.7346(4) 0.3302(3) 0.0371(12) Uani 1 1 d . . . H1A H 0.8649 0.7487 0.3842 0.044 Uiso 1 1 calc R . . H1B H 0.7792 0.7525 0.3206 0.044 Uiso 1 1 calc R . . C8 C 0.9241(5) 0.7006(5) -0.0537(3) 0.0469(13) Uani 1 1 d . . . H8A H 0.9156 0.6332 -0.0745 0.070 Uiso 1 1 calc R . . H8B H 0.9780 0.7349 -0.0809 0.070 Uiso 1 1 calc R . . H8C H 0.8617 0.7382 -0.0598 0.070 Uiso 1 1 calc R . . N5 N 1.1974(3) 0.4964(3) 0.2441(3) 0.0369(10) Uani 1 1 d . . . H5C H 1.2160 0.5314 0.2022 0.055 Uiso 1 1 calc R . . H5D H 1.2486 0.4563 0.2591 0.055 Uiso 1 1 calc R . . H5E H 1.1818 0.5397 0.2822 0.055 Uiso 1 1 calc R . . C11 C 0.6774(3) 0.5287(4) 0.2355(3) 0.0303(10) Uani 1 1 d . . . H11 H 0.7098 0.4617 0.2302 0.036 Uiso 1 1 calc R . . C2 C 0.9173(4) 0.7967(4) 0.2800(3) 0.0360(12) Uani 1 1 d . . . H2A H 0.9076 0.8685 0.2911 0.043 Uiso 1 1 calc R . . H2B H 0.9881 0.7797 0.2902 0.043 Uiso 1 1 calc R . . O6 O 0.6494(4) 0.6857(4) 0.7694(3) 0.0665(13) Uani 1 1 d . . . C14 C 0.7936(4) 0.5589(4) 0.3545(3) 0.0362(11) Uani 1 1 d . . . C4 C 0.9854(4) 0.9305(4) 0.1587(3) 0.0410(13) Uani 1 1 d . . . H4A H 0.9204 0.9642 0.1582 0.062 Uiso 1 1 calc R . . H4B H 1.0271 0.9567 0.1175 0.062 Uiso 1 1 calc R . . H4C H 1.0185 0.9426 0.2075 0.062 Uiso 1 1 calc R . . C6 C 0.9507(4) 0.6936(4) 0.0316(3) 0.0332(11) Uani 1 1 d . . . C13 C 0.6912(4) 0.5633(4) 0.3173(3) 0.0384(12) Uani 1 1 d . . . H13A H 0.6682 0.6336 0.3200 0.046 Uiso 1 1 calc R . . H13B H 0.6451 0.5235 0.3492 0.046 Uiso 1 1 calc R . . C9 C 0.7786(4) 0.6298(5) 0.0494(3) 0.0422(13) Uani 1 1 d . . . H9A H 0.7722 0.6066 -0.0037 0.051 Uiso 1 1 calc R . . H9B H 0.7555 0.7000 0.0520 0.051 Uiso 1 1 calc R . . O3 O 0.6729(4) 0.5687(3) 0.8646(3) 0.0643(13) Uani 1 1 d . . . O5 O 0.5229(3) 0.6586(4) 0.8589(3) 0.0682(14) Uani 1 1 d . . . C10 C 0.7143(4) 0.5642(5) 0.1019(3) 0.0424(13) Uani 1 1 d . . . H10A H 0.6432 0.5693 0.0870 0.051 Uiso 1 1 calc R . . H10B H 0.7351 0.4935 0.0972 0.051 Uiso 1 1 calc R . . C20 C 1.0620(5) 0.2753(4) 0.1502(4) 0.0539(16) Uani 1 1 d . . . H20 H 0.9982 0.3045 0.1306 0.065 Uiso 1 1 calc R . . C15 C 0.8363(4) 0.4532(4) 0.3512(4) 0.0443(13) Uani 1 1 d . . . H15A H 0.8451 0.4333 0.2981 0.066 Uiso 1 1 calc R . . H15B H 0.7902 0.4069 0.3763 0.066 Uiso 1 1 calc R . . H15C H 0.9011 0.4517 0.3771 0.066 Uiso 1 1 calc R . . C22 C 1.0382(8) 0.2164(6) 0.2197(6) 0.095(3) Uani 1 1 d . . . H22A H 1.1004 0.1945 0.2438 0.143 Uiso 1 1 calc R . . H22B H 0.9982 0.1578 0.2057 0.143 Uiso 1 1 calc R . . H22C H 1.0003 0.2581 0.2552 0.143 Uiso 1 1 calc R . . C7 C 1.0568(4) 0.6563(4) 0.0392(3) 0.0445(13) Uani 1 1 d . . . H7A H 1.0725 0.6461 0.0930 0.067 Uiso 1 1 calc R . . H7B H 1.1028 0.7058 0.0176 0.067 Uiso 1 1 calc R . . H7C H 1.0639 0.5929 0.0118 0.067 Uiso 1 1 calc R . . O4 O 0.6680(4) 0.7371(4) 0.8966(3) 0.0676(13) Uani 1 1 d . . . C3 C 0.9702(4) 0.8176(4) 0.1476(3) 0.0342(11) Uani 1 1 d . . . H3 H 1.0351 0.7827 0.1572 0.041 Uiso 1 1 calc R . . C12 C 0.5666(4) 0.5163(5) 0.2196(4) 0.0447(14) Uani 1 1 d . . . H12A H 0.5334 0.5814 0.2234 0.067 Uiso 1 1 calc R . . H12B H 0.5375 0.4702 0.2567 0.067 Uiso 1 1 calc R . . H12C H 0.5574 0.4893 0.1683 0.067 Uiso 1 1 calc R . . C21 C 1.1060(7) 0.2053(6) 0.0865(5) 0.073(2) Uani 1 1 d . . . H21A H 1.1707 0.1789 0.1031 0.109 Uiso 1 1 calc R . . H21B H 1.1150 0.2437 0.0396 0.109 Uiso 1 1 calc R . . H21C H 1.0598 0.1498 0.0772 0.109 Uiso 1 1 calc R . . C16 C 0.7816(5) 0.5877(5) 0.4382(3) 0.0491(14) Uani 1 1 d . . . H16A H 0.8478 0.5963 0.4612 0.074 Uiso 1 1 calc R . . H16B H 0.7453 0.5348 0.4650 0.074 Uiso 1 1 calc R . . H16C H 0.7442 0.6504 0.4419 0.074 Uiso 1 1 calc R . . Cl2 Cl 0.62843(9) 0.88500(10) 0.18524(9) 0.0393(3) Uani 1 1 d . . . O7 O 0.7178(4) 0.9398(4) 0.1839(4) 0.0791(15) Uiso 1 1 d . . . O8 O 0.5488(5) 0.9371(5) 0.1522(4) 0.0875(17) Uiso 1 1 d . . . O9 O 0.6135(6) 0.8256(6) 0.2443(5) 0.115(2) Uiso 1 1 d . . . O10 O 0.6494(6) 0.8093(6) 0.1278(5) 0.115(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 Ni1 0.0262(3) 0.0233(3) 0.0215(3) 0.0001(2) -0.0024(2) 0.0011(2) Cl1 0.0470(8) 0.0471(8) 0.0339(7) -0.0025(6) 0.0011(6) 0.0139(6) N3 0.036(2) 0.028(2) 0.029(2) -0.0048(16) -0.0006(17) 0.0021(17) O1 0.0344(17) 0.0291(16) 0.0303(18) 0.0016(15) -0.0015(16) -0.0005(13) N1 0.029(2) 0.036(2) 0.023(2) 0.0020(16) 0.0004(16) 0.0006(17) O2 0.0313(17) 0.0271(17) 0.0319(19) 0.0051(13) -0.0009(13) 0.0027(14) N4 0.0249(19) 0.032(2) 0.030(2) -0.0048(17) -0.0052(16) 0.0012(15) N2 0.033(2) 0.0231(18) 0.029(2) 0.0013(16) -0.0065(17) 0.0022(15) C5 0.041(3) 0.028(2) 0.035(3) 0.005(2) -0.010(2) -0.003(2) C18 0.041(3) 0.024(2) 0.030(3) 0.0068(19) 0.004(2) 0.006(2) C17 0.028(2) 0.029(2) 0.024(2) 0.0049(18) -0.0011(17) 0.0018(18) C19 0.044(3) 0.038(3) 0.036(3) 0.000(2) 0.010(2) 0.005(2) C1 0.043(3) 0.042(3) 0.026(3) -0.007(2) -0.002(2) 0.002(2) C8 0.058(3) 0.057(3) 0.025(3) 0.002(3) -0.002(3) -0.004(3) N5 0.031(2) 0.042(3) 0.038(2) 0.0070(19) -0.0009(18) 0.0059(19) C11 0.025(2) 0.035(3) 0.031(3) -0.001(2) 0.0023(19) 0.000(2) C2 0.047(3) 0.028(3) 0.033(3) -0.009(2) -0.009(2) -0.002(2) O6 0.086(3) 0.077(3) 0.037(2) 0.010(2) 0.008(2) 0.012(3) C14 0.038(3) 0.042(3) 0.028(3) 0.004(2) 0.003(2) -0.003(2) C4 0.045(3) 0.033(3) 0.045(3) 0.005(2) -0.013(3) -0.006(2) C6 0.049(3) 0.028(2) 0.023(2) 0.0030(18) 0.000(2) 0.002(2) C13 0.036(3) 0.051(3) 0.028(3) -0.006(2) 0.008(2) -0.001(2) C9 0.046(3) 0.049(3) 0.031(3) 0.002(2) -0.011(2) -0.010(3) O3 0.083(3) 0.044(2) 0.066(3) 0.002(2) 0.019(3) 0.022(2) O5 0.046(3) 0.094(4) 0.064(3) -0.005(3) 0.005(2) 0.024(2) C10 0.037(3) 0.061(4) 0.029(3) -0.007(2) -0.009(2) -0.012(3) C20 0.065(4) 0.033(3) 0.064(4) -0.010(3) 0.007(3) 0.006(3) C15 0.038(3) 0.051(3) 0.044(3) 0.021(3) 0.006(2) -0.001(2) C22 0.140(8) 0.056(5) 0.090(7) 0.005(4) 0.038(6) -0.029(5) C7 0.049(3) 0.047(3) 0.037(3) 0.011(2) 0.012(2) 0.007(3) O4 0.080(3) 0.069(3) 0.054(3) -0.009(2) -0.015(2) 0.002(3) C3 0.034(3) 0.030(3) 0.039(3) 0.002(2) -0.009(2) -0.003(2) C12 0.030(3) 0.057(4) 0.047(4) -0.013(3) 0.004(2) -0.006(3) C21 0.101(6) 0.054(4) 0.063(5) -0.018(4) 0.011(4) -0.020(4) C16 0.049(3) 0.073(4) 0.025(3) 0.008(3) 0.002(3) -0.006(3) Cl2 0.0343(6) 0.0394(7) 0.0443(9) 0.0139(6) -0.0035(6) 0.0024(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 Ni1 N4 2.084(4) . ? Ni1 N2 2.089(4) . ? Ni1 N3 2.117(5) . ? Ni1 N1 2.129(4) . ? Ni1 O2 2.139(3) . ? Ni1 O1 2.199(3) . ? Ni1 C17 2.479(4) . ? Cl1 O3 1.420(4) . ? Cl1 O4 1.421(5) . ? Cl1 O6 1.432(5) . ? Cl1 O5 1.436(5) . ? N3 C9 1.475(7) . ? N3 C6 1.496(7) . ? N3 H3A 0.9300 . ? O1 C17 1.253(6) . ? N1 C1 1.479(7) . ? N1 C14 1.504(7) . ? N1 H1C 0.9300 . ? O2 C17 1.265(6) . ? N4 C11 1.486(6) . ? N4 C10 1.487(6) . ? N4 H4D 0.9300 . ? N2 C2 1.468(6) . ? N2 C3 1.483(7) . ? N2 H2C 0.9300 . ? C5 C3 1.522(7) . ? C5 C6 1.564(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C18 N5 1.490(7) . ? C18 C17 1.520(6) . ? C18 C19 1.531(7) . ? C18 H18 1.0000 . ? C19 C20 1.506(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C1 C2 1.512(8) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C8 C6 1.547(7) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? N5 H5C 0.9100 . ? N5 H5D 0.9100 . ? N5 H5E 0.9100 . ? C11 C12 1.518(7) . ? C11 C13 1.525(7) . ? C11 H11 1.0000 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C14 C13 1.520(8) . ? C14 C15 1.525(8) . ? C14 C16 1.532(8) . ? C4 C3 1.538(7) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 C7 1.511(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C9 C10 1.537(8) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C20 C22 1.491(10) . ? C20 C21 1.575(9) . ? C20 H20 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C3 H3 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? Cl2 O9 1.324(8) . ? Cl2 O8 1.400(6) . ? Cl2 O7 1.403(6) . ? Cl2 O10 1.459(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 N4 Ni1 N2 103.80(15) . . ? N4 Ni1 N3 85.40(16) . . ? N2 Ni1 N3 92.06(16) . . ? N4 Ni1 N1 91.10(16) . . ? N2 Ni1 N1 85.52(16) . . ? N3 Ni1 N1 175.16(16) . . ? N4 Ni1 O2 162.10(14) . . ? N2 Ni1 O2 93.48(14) . . ? N3 Ni1 O2 98.81(14) . . ? N1 Ni1 O2 85.54(15) . . ? N4 Ni1 O1 102.03(14) . . ? N2 Ni1 O1 154.10(14) . . ? N3 Ni1 O1 88.17(14) . . ? N1 Ni1 O1 95.83(15) . . ? O2 Ni1 O1 60.97(12) . . ? N4 Ni1 C17 131.95(15) . . ? N2 Ni1 C17 124.14(15) . . ? N3 Ni1 C17 95.18(15) . . ? N1 Ni1 C17 89.64(16) . . ? O2 Ni1 C17 30.68(14) . . ? O1 Ni1 C17 30.33(14) . . ? O3 Cl1 O4 109.8(3) . . ? O3 Cl1 O6 108.5(3) . . ? O4 Cl1 O6 111.4(3) . . ? O3 Cl1 O5 110.2(3) . . ? O4 Cl1 O5 107.6(3) . . ? O6 Cl1 O5 109.4(3) . . ? C9 N3 C6 112.9(4) . . ? C9 N3 Ni1 105.7(3) . . ? C6 N3 Ni1 121.3(3) . . ? C9 N3 H3A 105.2 . . ? C6 N3 H3A 105.2 . . ? Ni1 N3 H3A 105.2 . . ? C17 O1 Ni1 87.3(3) . . ? C1 N1 C14 114.3(4) . . ? C1 N1 Ni1 103.7(3) . . ? C14 N1 Ni1 120.3(3) . . ? C1 N1 H1C 105.8 . . ? C14 N1 H1C 105.8 . . ? Ni1 N1 H1C 105.8 . . ? C17 O2 Ni1 89.7(3) . . ? C11 N4 C10 111.1(4) . . ? C11 N4 Ni1 117.8(3) . . ? C10 N4 Ni1 104.9(3) . . ? C11 N4 H4D 107.5 . . ? C10 N4 H4D 107.5 . . ? Ni1 N4 H4D 107.5 . . ? C2 N2 C3 112.4(4) . . ? C2 N2 Ni1 104.3(3) . . ? C3 N2 Ni1 113.3(3) . . ? C2 N2 H2C 108.9 . . ? C3 N2 H2C 108.9 . . ? Ni1 N2 H2C 108.9 . . ? C3 C5 C6 117.9(4) . . ? C3 C5 H5A 107.8 . . ? C6 C5 H5A 107.8 . . ? C3 C5 H5B 107.8 . . ? C6 C5 H5B 107.8 . . ? H5A C5 H5B 107.2 . . ? N5 C18 C17 107.9(4) . . ? N5 C18 C19 109.8(4) . . ? C17 C18 C19 115.0(4) . . ? N5 C18 H18 108.0 . . ? C17 C18 H18 108.0 . . ? C19 C18 H18 108.0 . . ? O1 C17 O2 121.9(4) . . ? O1 C17 C18 119.7(4) . . ? O2 C17 C18 118.4(4) . . ? O1 C17 Ni1 62.4(2) . . ? O2 C17 Ni1 59.6(2) . . ? C18 C17 Ni1 173.8(3) . . ? C20 C19 C18 116.4(5) . . ? C20 C19 H19A 108.2 . . ? C18 C19 H19A 108.2 . . ? C20 C19 H19B 108.2 . . ? C18 C19 H19B 108.2 . . ? H19A C19 H19B 107.3 . . ? N1 C1 C2 109.8(4) . . ? N1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? N1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C18 N5 H5C 109.5 . . ? C18 N5 H5D 109.5 . . ? H5C N5 H5D 109.5 . . ? C18 N5 H5E 109.5 . . ? H5C N5 H5E 109.5 . . ? H5D N5 H5E 109.5 . . ? N4 C11 C12 112.8(4) . . ? N4 C11 C13 111.0(4) . . ? C12 C11 C13 109.1(4) . . ? N4 C11 H11 107.9 . . ? C12 C11 H11 107.9 . . ? C13 C11 H11 107.9 . . ? N2 C2 C1 109.5(4) . . ? N2 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? N2 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? N1 C14 C13 110.5(4) . . ? N1 C14 C15 107.9(4) . . ? C13 C14 C15 111.0(5) . . ? N1 C14 C16 111.5(4) . . ? C13 C14 C16 108.0(4) . . ? C15 C14 C16 108.0(5) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C6 C7 108.1(4) . . ? N3 C6 C8 112.6(4) . . ? C7 C6 C8 108.8(4) . . ? N3 C6 C5 109.8(4) . . ? C7 C6 C5 110.7(4) . . ? C8 C6 C5 106.9(4) . . ? C14 C13 C11 120.3(4) . . ? C14 C13 H13A 107.3 . . ? C11 C13 H13A 107.3 . . ? C14 C13 H13B 107.3 . . ? C11 C13 H13B 107.3 . . ? H13A C13 H13B 106.9 . . ? N3 C9 C10 109.0(4) . . ? N3 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? N3 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N4 C10 C9 109.2(4) . . ? N4 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? N4 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? C22 C20 C19 114.5(6) . . ? C22 C20 C21 110.5(6) . . ? C19 C20 C21 108.0(5) . . ? C22 C20 H20 107.9 . . ? C19 C20 H20 107.9 . . ? C21 C20 H20 107.9 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C3 C5 111.2(4) . . ? N2 C3 C4 112.0(4) . . ? C5 C3 C4 107.2(4) . . ? N2 C3 H3 108.8 . . ? C5 C3 H3 108.8 . . ? C4 C3 H3 108.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O9 Cl2 O8 120.7(4) . . ? O9 Cl2 O7 117.1(4) . . ? O8 Cl2 O7 112.5(4) . . ? O9 Cl2 O10 99.1(5) . . ? O8 Cl2 O10 101.8(4) . . ? O7 Cl2 O10 100.8(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 N4 Ni1 N3 C9 11.9(3) . . . . ? N2 Ni1 N3 C9 -91.7(3) . . . . ? N1 Ni1 N3 C9 -31.9(19) . . . . ? O2 Ni1 N3 C9 174.4(3) . . . . ? O1 Ni1 N3 C9 114.2(3) . . . . ? C17 Ni1 N3 C9 143.7(3) . . . . ? N4 Ni1 N3 C6 142.0(4) . . . . ? N2 Ni1 N3 C6 38.3(4) . . . . ? N1 Ni1 N3 C6 98.2(18) . . . . ? O2 Ni1 N3 C6 -55.6(4) . . . . ? O1 Ni1 N3 C6 -115.8(3) . . . . ? C17 Ni1 N3 C6 -86.3(4) . . . . ? N4 Ni1 O1 C17 -171.6(3) . . . . ? N2 Ni1 O1 C17 12.5(5) . . . . ? N3 Ni1 O1 C17 103.5(3) . . . . ? N1 Ni1 O1 C17 -79.2(3) . . . . ? O2 Ni1 O1 C17 2.4(3) . . . . ? N4 Ni1 N1 C1 -91.2(3) . . . . ? N2 Ni1 N1 C1 12.5(3) . . . . ? N3 Ni1 N1 C1 -47.6(19) . . . . ? O2 Ni1 N1 C1 106.4(3) . . . . ? O1 Ni1 N1 C1 166.5(3) . . . . ? C17 Ni1 N1 C1 136.8(3) . . . . ? N4 Ni1 N1 C14 38.1(4) . . . . ? N2 Ni1 N1 C14 141.8(4) . . . . ? N3 Ni1 N1 C14 81.7(18) . . . . ? O2 Ni1 N1 C14 -124.3(4) . . . . ? O1 Ni1 N1 C14 -64.1(4) . . . . ? C17 Ni1 N1 C14 -93.9(4) . . . . ? N4 Ni1 O2 C17 17.2(6) . . . . ? N2 Ni1 O2 C17 -177.9(3) . . . . ? N3 Ni1 O2 C17 -85.3(3) . . . . ? N1 Ni1 O2 C17 96.9(3) . . . . ? O1 Ni1 O2 C17 -2.3(2) . . . . ? N2 Ni1 N4 C11 -127.1(3) . . . . ? N3 Ni1 N4 C11 141.9(3) . . . . ? N1 Ni1 N4 C11 -41.5(3) . . . . ? O2 Ni1 N4 C11 37.3(7) . . . . ? O1 Ni1 N4 C11 54.7(3) . . . . ? C17 Ni1 N4 C11 49.0(4) . . . . ? N2 Ni1 N4 C10 108.7(3) . . . . ? N3 Ni1 N4 C10 17.7(3) . . . . ? N1 Ni1 N4 C10 -165.7(3) . . . . ? O2 Ni1 N4 C10 -86.8(6) . . . . ? O1 Ni1 N4 C10 -69.5(3) . . . . ? C17 Ni1 N4 C10 -75.1(4) . . . . ? N4 Ni1 N2 C2 107.4(3) . . . . ? N3 Ni1 N2 C2 -166.9(3) . . . . ? N1 Ni1 N2 C2 17.3(3) . . . . ? O2 Ni1 N2 C2 -67.9(3) . . . . ? O1 Ni1 N2 C2 -76.8(5) . . . . ? C17 Ni1 N2 C2 -69.2(4) . . . . ? N4 Ni1 N2 C3 -130.1(3) . . . . ? N3 Ni1 N2 C3 -44.3(3) . . . . ? N1 Ni1 N2 C3 139.9(3) . . . . ? O2 Ni1 N2 C3 54.6(3) . . . . ? O1 Ni1 N2 C3 45.7(5) . . . . ? C17 Ni1 N2 C3 53.3(4) . . . . ? Ni1 O1 C17 O2 -4.1(4) . . . . ? Ni1 O1 C17 C18 173.4(4) . . . . ? Ni1 O2 C17 O1 4.2(5) . . . . ? Ni1 O2 C17 C18 -173.3(4) . . . . ? N5 C18 C17 O1 178.7(4) . . . . ? C19 C18 C17 O1 55.9(6) . . . . ? N5 C18 C17 O2 -3.7(6) . . . . ? C19 C18 C17 O2 -126.5(5) . . . . ? N5 C18 C17 Ni1 -73(3) . . . . ? C19 C18 C17 Ni1 164(3) . . . . ? N4 Ni1 C17 O1 11.1(4) . . . . ? N2 Ni1 C17 O1 -173.4(3) . . . . ? N3 Ni1 C17 O1 -77.4(3) . . . . ? N1 Ni1 C17 O1 102.2(3) . . . . ? O2 Ni1 C17 O1 -175.9(4) . . . . ? N4 Ni1 C17 O2 -173.0(2) . . . . ? N2 Ni1 C17 O2 2.5(3) . . . . ? N3 Ni1 C17 O2 98.5(3) . . . . ? N1 Ni1 C17 O2 -81.8(3) . . . . ? O1 Ni1 C17 O2 175.9(4) . . . . ? N4 Ni1 C17 C18 -100(3) . . . . ? N2 Ni1 C17 C18 75(3) . . . . ? N3 Ni1 C17 C18 171(3) . . . . ? N1 Ni1 C17 C18 -9(3) . . . . ? O2 Ni1 C17 C18 73(3) . . . . ? O1 Ni1 C17 C18 -111(3) . . . . ? N5 C18 C19 C20 166.0(5) . . . . ? C17 C18 C19 C20 -72.2(6) . . . . ? C14 N1 C1 C2 -173.1(4) . . . . ? Ni1 N1 C1 C2 -40.3(4) . . . . ? C10 N4 C11 C12 -57.7(5) . . . . ? Ni1 N4 C11 C12 -178.7(3) . . . . ? C10 N4 C11 C13 179.5(4) . . . . ? Ni1 N4 C11 C13 58.6(5) . . . . ? C3 N2 C2 C1 -167.7(4) . . . . ? Ni1 N2 C2 C1 -44.6(4) . . . . ? N1 C1 C2 N2 60.3(5) . . . . ? C1 N1 C14 C13 74.4(6) . . . . ? Ni1 N1 C14 C13 -49.9(5) . . . . ? C1 N1 C14 C15 -164.1(4) . . . . ? Ni1 N1 C14 C15 71.5(5) . . . . ? C1 N1 C14 C16 -45.7(6) . . . . ? Ni1 N1 C14 C16 -170.1(4) . . . . ? C9 N3 C6 C7 -159.7(5) . . . . ? Ni1 N3 C6 C7 73.4(5) . . . . ? C9 N3 C6 C8 -39.5(6) . . . . ? Ni1 N3 C6 C8 -166.4(3) . . . . ? C9 N3 C6 C5 79.4(5) . . . . ? Ni1 N3 C6 C5 -47.4(5) . . . . ? C3 C5 C6 N3 62.1(6) . . . . ? C3 C5 C6 C7 -57.2(6) . . . . ? C3 C5 C6 C8 -175.5(5) . . . . ? N1 C14 C13 C11 63.7(6) . . . . ? C15 C14 C13 C11 -55.9(6) . . . . ? C16 C14 C13 C11 -174.1(5) . . . . ? N4 C11 C13 C14 -69.3(6) . . . . ? C12 C11 C13 C14 165.8(5) . . . . ? C6 N3 C9 C10 -173.7(4) . . . . ? Ni1 N3 C9 C10 -38.9(5) . . . . ? C11 N4 C10 C9 -172.3(4) . . . . ? Ni1 N4 C10 C9 -44.0(5) . . . . ? N3 C9 C10 N4 57.9(6) . . . . ? C18 C19 C20 C22 -53.2(8) . . . . ? C18 C19 C20 C21 -176.7(6) . . . . ? C2 N2 C3 C5 -176.5(4) . . . . ? Ni1 N2 C3 C5 65.6(4) . . . . ? C2 N2 C3 C4 -56.6(5) . . . . ? Ni1 N2 C3 C4 -174.6(3) . . . . ? C6 C5 C3 N2 -75.0(6) . . . . ? C6 C5 C3 C4 162.3(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5C O4 0.91 2.17 2.999(7) 151.8 3_754 N5 H5C O5 0.91 2.35 3.084(7) 137.5 3_754 N5 H5D O3 0.91 2.16 2.876(6) 135.0 2_764 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.01 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.262 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.119