# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Lisa Berreau' 'Atta M. Arif' 'Magdalena M. Makowska-Grzyska' 'Katarzyna Rudzka' 'Ewa Szajna' _publ_contact_author_name 'Lisa Berreau' _publ_contact_author_address ; Chemistry and Biochemistry Utah State University 0300 Old Main Hill Logan UT 84322-0300 UNITED STATES OF AMERICA ; _publ_contact_author_email BERREAU@CC.USU.EDU _publ_section_title ; Neutral acetohydroxamic acid coordination to a mononuclear Ni(II) center stabilized by a intramolecular hydrogen-bonding interaction ; data_usu115 _database_code_depnum_ccdc_archive 'CCDC 250014' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H40 N6 Ni O3, C H4 O, 2(Cl O4)' _chemical_formula_sum 'C38 H44 Cl2 N6 Ni O12' _chemical_formula_weight 906.40 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 19.2023(5) _cell_length_b 34.9478(9) _cell_length_c 12.2308(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8207.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 8985 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3776 _exptl_absorpt_coefficient_mu 0.672 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7987 _exptl_absorpt_correction_T_max 0.8499 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; The program Denzo-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL-97 input file. ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD Diffractometer' _diffrn_measurement_method 'Phi plus Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16542 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.48 _reflns_number_total 9172 _reflns_number_gt 6241 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX, Ortep3' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+15.2250P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00068(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9172 _refine_ls_number_parameters 550 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1440 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.00599(2) 0.112484(12) 0.05270(3) 0.02424(12) Uani 1 1 d . . . Cl1 Cl 0.46406(5) 0.21688(3) 0.12144(8) 0.0407(2) Uani 1 1 d . . . Cl2 Cl 0.14886(5) 0.03827(3) 0.53256(7) 0.0364(2) Uani 1 1 d . . . O1 O -0.01834(12) 0.11930(6) -0.10850(19) 0.0296(5) Uani 1 1 d . . . O2 O 0.04793(12) 0.16703(6) 0.02840(19) 0.0281(5) Uani 1 1 d D . . O3 O -0.07528(12) 0.14552(7) 0.10308(19) 0.0325(5) Uani 1 1 d . . . O4 O 0.40388(16) 0.24042(9) 0.1350(3) 0.0613(9) Uani 1 1 d . . . O5 O 0.50320(15) 0.22948(8) 0.0264(2) 0.0529(8) Uani 1 1 d . . . O6 O 0.50861(16) 0.21943(9) 0.2143(2) 0.0575(8) Uani 1 1 d . . . O7 O 0.44380(14) 0.17775(8) 0.1051(3) 0.0533(8) Uani 1 1 d . . . O8 O 0.1824(2) 0.06535(11) 0.4644(3) 0.0930(13) Uani 1 1 d . . . O9 O 0.18002(15) 0.00162(8) 0.5178(2) 0.0485(7) Uani 1 1 d . . . O10 O 0.15713(17) 0.05020(9) 0.6435(2) 0.0568(8) Uani 1 1 d . . . O11 O 0.07699(16) 0.03673(12) 0.5078(3) 0.0856(13) Uani 1 1 d . . . O12 O 0.20587(19) 0.12804(10) 0.6545(3) 0.0735(10) Uani 1 1 d . . . H12 H 0.2134 0.1054 0.6351 0.088 Uiso 1 1 calc R . . N1 N 0.09332(16) 0.11534(8) -0.1745(2) 0.0335(7) Uani 1 1 d D . . N2 N 0.09882(13) 0.09042(7) 0.0051(2) 0.0243(6) Uani 1 1 d . . . N3 N 0.04758(13) 0.10106(7) 0.2109(2) 0.0257(6) Uani 1 1 d . . . N4 N -0.05557(13) 0.06459(7) 0.0996(2) 0.0256(6) Uani 1 1 d . . . N5 N 0.15629(14) 0.16581(8) 0.1443(2) 0.0284(6) Uani 1 1 d . . . N6 N -0.00531(15) 0.19332(9) 0.0461(3) 0.0358(7) Uani 1 1 d . . . C1 C 0.0222(3) 0.12575(13) -0.3868(3) 0.0530(11) Uani 1 1 d . . . H1A H 0.0727 0.1225 -0.3927 0.079 Uiso 1 1 calc R . . H1B H 0.0051 0.1399 -0.4506 0.079 Uiso 1 1 calc R . . H1C H -0.0003 0.1006 -0.3840 0.079 Uiso 1 1 calc R . . C2 C -0.0722(3) 0.15678(18) -0.2787(4) 0.0816(18) Uani 1 1 d . . . H2A H -0.0986 0.1328 -0.2826 0.122 Uiso 1 1 calc R . . H2B H -0.0847 0.1731 -0.3407 0.122 Uiso 1 1 calc R . . H2C H -0.0831 0.1700 -0.2102 0.122 Uiso 1 1 calc R . . C3 C 0.0452(3) 0.18618(13) -0.2800(4) 0.0744(16) Uani 1 1 d . . . H3A H 0.0355 0.1995 -0.2112 0.112 Uiso 1 1 calc R . . H3B H 0.0304 0.2022 -0.3415 0.112 Uiso 1 1 calc R . . H3C H 0.0953 0.1811 -0.2857 0.112 Uiso 1 1 calc R . . C4 C 0.0051(2) 0.14806(11) -0.2828(3) 0.0413(9) Uani 1 1 d . . . C5 C 0.02495(19) 0.12584(10) -0.1815(3) 0.0318(8) Uani 1 1 d . . . C6 C 0.13031(17) 0.09776(9) -0.0901(3) 0.0280(7) Uani 1 1 d . . . C7 C 0.20089(18) 0.08951(10) -0.1068(3) 0.0343(8) Uani 1 1 d . . . H7 H 0.2226 0.0949 -0.1748 0.041 Uiso 1 1 calc R . . C8 C 0.23779(18) 0.07339(10) -0.0226(3) 0.0351(8) Uani 1 1 d . . . H8 H 0.2858 0.0677 -0.0319 0.042 Uiso 1 1 calc R . . C9 C 0.20525(17) 0.06530(10) 0.0762(3) 0.0316(8) Uani 1 1 d . . . H9 H 0.2303 0.0536 0.1343 0.038 Uiso 1 1 calc R . . C10 C 0.13628(16) 0.07453(9) 0.0880(3) 0.0255(7) Uani 1 1 d . . . C11 C 0.09530(17) 0.06808(9) 0.1910(3) 0.0279(7) Uani 1 1 d . . . H11A H 0.0678 0.0442 0.1843 0.033 Uiso 1 1 calc R . . H11B H 0.1275 0.0652 0.2536 0.033 Uiso 1 1 calc R . . C12 C -0.01402(17) 0.08892(10) 0.2757(3) 0.0298(7) Uani 1 1 d . . . H12A H -0.0386 0.1119 0.3031 0.036 Uiso 1 1 calc R . . H12B H 0.0018 0.0739 0.3398 0.036 Uiso 1 1 calc R . . C13 C -0.06355(17) 0.06516(9) 0.2095(3) 0.0276(7) Uani 1 1 d . . . C14 C -0.11640(18) 0.04514(10) 0.2623(3) 0.0334(8) Uani 1 1 d . . . H14 H -0.1201 0.0457 0.3398 0.040 Uiso 1 1 calc R . . C15 C -0.16318(18) 0.02455(10) 0.2008(3) 0.0357(8) Uani 1 1 d . . . H15 H -0.2007 0.0114 0.2349 0.043 Uiso 1 1 calc R . . C16 C -0.15485(18) 0.02317(10) 0.0888(3) 0.0335(8) Uani 1 1 d . . . H16 H -0.1866 0.0089 0.0453 0.040 Uiso 1 1 calc R . . C17 C -0.09993(17) 0.04269(9) 0.0391(3) 0.0275(7) Uani 1 1 d . . . C18 C -0.08753(17) 0.03851(9) -0.0794(3) 0.0284(7) Uani 1 1 d . . . C19 C -0.02005(17) 0.03404(9) -0.1199(3) 0.0299(7) Uani 1 1 d . . . H19 H 0.0183 0.0342 -0.0708 0.036 Uiso 1 1 calc R . . C20 C -0.00839(19) 0.02942(10) -0.2312(3) 0.0352(8) Uani 1 1 d . . . H20 H 0.0378 0.0272 -0.2582 0.042 Uiso 1 1 calc R . . C21 C -0.0643(2) 0.02808(11) -0.3028(3) 0.0413(9) Uani 1 1 d . . . H21 H -0.0566 0.0247 -0.3789 0.050 Uiso 1 1 calc R . . C22 C -0.1313(2) 0.03166(11) -0.2628(3) 0.0416(9) Uani 1 1 d . . . H22 H -0.1696 0.0305 -0.3118 0.050 Uiso 1 1 calc R . . C23 C -0.14336(19) 0.03699(10) -0.1521(3) 0.0356(8) Uani 1 1 d . . . H23 H -0.1897 0.0396 -0.1258 0.043 Uiso 1 1 calc R . . C24 C 0.08296(17) 0.13211(10) 0.2747(3) 0.0305(7) Uani 1 1 d . . . H24A H 0.0874 0.1237 0.3516 0.037 Uiso 1 1 calc R . . H24B H 0.0529 0.1551 0.2739 0.037 Uiso 1 1 calc R . . C25 C 0.15402(17) 0.14310(9) 0.2333(3) 0.0287(7) Uani 1 1 d . . . C26 C 0.21422(18) 0.13092(10) 0.2845(3) 0.0345(8) Uani 1 1 d . . . H26 H 0.2117 0.1156 0.3485 0.041 Uiso 1 1 calc R . . C27 C 0.2779(2) 0.14120(10) 0.2417(3) 0.0408(9) Uani 1 1 d . . . H27 H 0.3198 0.1328 0.2754 0.049 Uiso 1 1 calc R . . C28 C 0.28019(19) 0.16383(10) 0.1492(3) 0.0372(8) Uani 1 1 d . . . H28 H 0.3237 0.1711 0.1186 0.045 Uiso 1 1 calc R . . C29 C 0.21787(18) 0.17601(9) 0.1009(3) 0.0306(7) Uani 1 1 d . . . C30 C 0.21706(18) 0.20120(10) 0.0036(3) 0.0346(8) Uani 1 1 d . . . C31 C 0.2657(2) 0.19550(12) -0.0791(3) 0.0476(10) Uani 1 1 d . . . H31 H 0.2992 0.1757 -0.0724 0.057 Uiso 1 1 calc R . . C32 C 0.2655(3) 0.21855(14) -0.1712(4) 0.0590(12) Uani 1 1 d . . . H32 H 0.2988 0.2145 -0.2276 0.071 Uiso 1 1 calc R . . C33 C 0.2173(3) 0.24704(15) -0.1806(4) 0.0653(14) Uani 1 1 d . . . H33 H 0.2172 0.2627 -0.2440 0.078 Uiso 1 1 calc R . . C34 C 0.1687(2) 0.25345(13) -0.0993(4) 0.0606(13) Uani 1 1 d . . . H34 H 0.1355 0.2734 -0.1070 0.073 Uiso 1 1 calc R . . C35 C 0.1687(2) 0.23069(11) -0.0067(4) 0.0457(10) Uani 1 1 d . . . H35 H 0.1357 0.2352 0.0498 0.055 Uiso 1 1 calc R . . C36 C -0.06632(19) 0.18023(11) 0.0824(3) 0.0365(8) Uani 1 1 d . . . C37 C -0.1236(2) 0.20922(12) 0.0969(3) 0.0442(9) Uani 1 1 d . . . H37A H -0.1651 0.2008 0.0567 0.066 Uiso 1 1 calc R . . H37B H -0.1082 0.2341 0.0688 0.066 Uiso 1 1 calc R . . H37C H -0.1349 0.2116 0.1748 0.066 Uiso 1 1 calc R . . C38 C 0.2408(5) 0.1523(2) 0.5875(5) 0.160(4) Uani 1 1 d . . . H38A H 0.2591 0.1738 0.6303 0.241 Uiso 1 1 calc R . . H38B H 0.2091 0.1620 0.5312 0.241 Uiso 1 1 calc R . . H38C H 0.2795 0.1387 0.5527 0.241 Uiso 1 1 calc R . . H6N H 0.0081(18) 0.2171(11) 0.017(3) 0.032(10) Uiso 1 1 d . . . H1N H 0.1185(19) 0.1222(12) -0.230(2) 0.052(13) Uiso 1 1 d D . . H2 H 0.0801(19) 0.1721(14) 0.072(3) 0.076(17) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0220(2) 0.0243(2) 0.0264(2) 0.00059(16) 0.00141(17) 0.00142(17) Cl1 0.0455(5) 0.0320(5) 0.0446(6) 0.0023(4) 0.0029(4) 0.0040(4) Cl2 0.0371(5) 0.0359(5) 0.0363(5) 0.0020(4) 0.0006(4) 0.0037(4) O1 0.0283(12) 0.0279(13) 0.0325(13) -0.0004(10) -0.0044(10) 0.0019(10) O2 0.0244(12) 0.0255(12) 0.0343(13) 0.0011(10) -0.0003(10) 0.0042(10) O3 0.0307(13) 0.0299(13) 0.0368(13) 0.0012(10) 0.0067(10) 0.0021(10) O4 0.068(2) 0.0522(19) 0.064(2) 0.0110(15) 0.0161(16) 0.0240(16) O5 0.0627(19) 0.0454(17) 0.0507(17) 0.0101(13) 0.0157(14) -0.0001(14) O6 0.073(2) 0.0501(18) 0.0492(18) 0.0004(13) -0.0151(15) -0.0031(16) O7 0.0418(16) 0.0381(16) 0.080(2) 0.0031(15) 0.0012(15) -0.0057(13) O8 0.141(4) 0.058(2) 0.081(3) 0.0314(19) 0.043(2) 0.000(2) O9 0.0533(17) 0.0411(16) 0.0510(17) 0.0006(13) 0.0079(13) 0.0129(13) O10 0.085(2) 0.0523(18) 0.0328(15) -0.0079(13) -0.0102(15) 0.0061(16) O11 0.0440(18) 0.106(3) 0.107(3) -0.056(2) -0.0240(19) 0.0231(19) O12 0.095(3) 0.070(2) 0.055(2) -0.0029(17) 0.0191(19) -0.028(2) N1 0.0364(17) 0.0335(16) 0.0306(17) 0.0046(13) 0.0052(13) 0.0051(14) N2 0.0232(13) 0.0227(13) 0.0269(14) 0.0010(11) 0.0006(11) 0.0012(11) N3 0.0238(14) 0.0250(14) 0.0282(15) -0.0011(11) 0.0004(11) -0.0006(11) N4 0.0233(14) 0.0228(14) 0.0306(15) 0.0020(11) 0.0021(11) 0.0002(11) N5 0.0271(14) 0.0242(14) 0.0338(16) -0.0022(11) 0.0002(12) -0.0024(11) N6 0.0345(17) 0.0280(16) 0.0448(18) 0.0006(13) -0.0008(14) 0.0052(13) C1 0.077(3) 0.050(3) 0.031(2) 0.0022(18) -0.008(2) 0.015(2) C2 0.069(3) 0.123(5) 0.053(3) 0.030(3) 0.002(3) 0.048(3) C3 0.129(5) 0.036(2) 0.058(3) 0.012(2) -0.013(3) 0.007(3) C4 0.050(2) 0.039(2) 0.034(2) 0.0065(16) -0.0006(17) 0.0131(18) C5 0.039(2) 0.0254(17) 0.0305(19) -0.0011(14) 0.0002(15) 0.0041(15) C6 0.0305(17) 0.0214(16) 0.0321(18) -0.0021(13) 0.0028(14) 0.0023(13) C7 0.0332(19) 0.0342(19) 0.0356(19) -0.0024(15) 0.0084(15) 0.0018(15) C8 0.0248(17) 0.035(2) 0.045(2) -0.0048(16) 0.0052(15) 0.0064(15) C9 0.0287(18) 0.0277(17) 0.039(2) -0.0009(14) -0.0013(15) 0.0051(14) C10 0.0276(17) 0.0181(15) 0.0309(18) -0.0009(12) -0.0016(13) 0.0020(13) C11 0.0293(17) 0.0230(16) 0.0314(18) 0.0016(13) -0.0015(14) -0.0003(14) C12 0.0300(18) 0.0341(18) 0.0252(17) -0.0005(14) 0.0031(14) -0.0014(14) C13 0.0275(17) 0.0241(16) 0.0313(19) 0.0002(13) 0.0030(14) 0.0037(13) C14 0.0327(19) 0.0318(18) 0.036(2) 0.0022(15) 0.0073(15) -0.0010(15) C15 0.0300(18) 0.037(2) 0.041(2) 0.0052(16) 0.0079(15) -0.0037(16) C16 0.0270(18) 0.0316(19) 0.042(2) -0.0004(15) 0.0016(15) -0.0032(15) C17 0.0260(16) 0.0218(16) 0.0347(19) 0.0009(13) -0.0017(14) 0.0042(13) C18 0.0295(17) 0.0210(16) 0.0348(19) 0.0001(13) -0.0018(14) -0.0006(13) C19 0.0299(18) 0.0251(17) 0.0348(19) -0.0013(14) 0.0000(14) -0.0006(14) C20 0.041(2) 0.0251(17) 0.039(2) -0.0023(14) 0.0066(17) -0.0026(15) C21 0.058(3) 0.036(2) 0.030(2) 0.0002(15) 0.0008(18) -0.0024(18) C22 0.046(2) 0.042(2) 0.037(2) 0.0012(16) -0.0110(18) -0.0018(18) C23 0.0303(19) 0.038(2) 0.039(2) 0.0034(16) -0.0045(15) -0.0007(15) C24 0.0321(18) 0.0318(18) 0.0277(18) -0.0017(14) 0.0017(14) -0.0018(14) C25 0.0308(18) 0.0266(17) 0.0288(18) -0.0013(13) -0.0015(14) -0.0008(14) C26 0.037(2) 0.0304(19) 0.036(2) 0.0029(15) -0.0076(16) -0.0040(15) C27 0.035(2) 0.034(2) 0.053(2) 0.0028(17) -0.0150(18) -0.0014(16) C28 0.0298(18) 0.035(2) 0.046(2) 0.0001(16) -0.0017(16) -0.0047(15) C29 0.0332(18) 0.0230(16) 0.0356(19) -0.0037(14) -0.0006(15) -0.0021(14) C30 0.0322(19) 0.0311(19) 0.040(2) 0.0042(15) -0.0008(16) -0.0091(15) C31 0.046(2) 0.045(2) 0.053(3) 0.0033(19) 0.005(2) -0.0087(19) C32 0.064(3) 0.068(3) 0.045(3) 0.009(2) 0.009(2) -0.019(3) C33 0.066(3) 0.068(3) 0.062(3) 0.032(3) -0.009(3) -0.025(3) C34 0.050(3) 0.046(3) 0.085(3) 0.030(2) -0.013(3) -0.009(2) C35 0.036(2) 0.039(2) 0.062(3) 0.0116(19) 0.0017(19) -0.0063(17) C36 0.037(2) 0.037(2) 0.035(2) -0.0009(15) 0.0008(16) 0.0033(16) C37 0.044(2) 0.043(2) 0.045(2) 0.0050(18) 0.0045(18) 0.0099(18) C38 0.268(11) 0.151(7) 0.062(4) -0.018(4) 0.036(5) -0.141(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N2 2.027(3) . ? Ni1 O3 2.037(2) . ? Ni1 O1 2.040(2) . ? Ni1 O2 2.091(2) . ? Ni1 N4 2.128(3) . ? Ni1 N3 2.130(3) . ? Cl1 O6 1.424(3) . ? Cl1 O4 1.428(3) . ? Cl1 O7 1.436(3) . ? Cl1 O5 1.453(3) . ? Cl2 O11 1.414(3) . ? Cl2 O8 1.415(3) . ? Cl2 O9 1.425(3) . ? Cl2 O10 1.428(3) . ? O1 C5 1.241(4) . ? O2 N6 1.391(4) . ? O2 H2 0.838(19) . ? O3 C36 1.251(4) . ? O12 C38 1.357(7) . ? O12 H12 0.8400 . ? N1 C5 1.366(5) . ? N1 C6 1.396(4) . ? N1 H1N 0.867(19) . ? N2 C6 1.337(4) . ? N2 C10 1.361(4) . ? N3 C12 1.486(4) . ? N3 C11 1.493(4) . ? N3 C24 1.499(4) . ? N4 C13 1.353(4) . ? N4 C17 1.363(4) . ? N5 C29 1.344(4) . ? N5 C25 1.348(4) . ? N6 C36 1.334(5) . ? N6 H6N 0.94(4) . ? C1 C4 1.528(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.515(6) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.539(6) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.511(5) . ? C6 C7 1.401(5) . ? C7 C8 1.371(5) . ? C7 H7 0.9500 . ? C8 C9 1.389(5) . ? C8 H8 0.9500 . ? C9 C10 1.371(4) . ? C9 H9 0.9500 . ? C10 C11 1.502(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.500(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.392(5) . ? C14 C15 1.375(5) . ? C14 H14 0.9500 . ? C15 C16 1.380(5) . ? C15 H15 0.9500 . ? C16 C17 1.395(5) . ? C16 H16 0.9500 . ? C17 C18 1.477(5) . ? C18 C23 1.393(5) . ? C18 C19 1.396(5) . ? C19 C20 1.389(5) . ? C19 H19 0.9500 . ? C20 C21 1.386(5) . ? C20 H20 0.9500 . ? C21 C22 1.382(5) . ? C21 H21 0.9500 . ? C22 C23 1.386(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.505(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.382(5) . ? C26 C27 1.379(5) . ? C26 H26 0.9500 . ? C27 C28 1.381(5) . ? C27 H27 0.9500 . ? C28 C29 1.401(5) . ? C28 H28 0.9500 . ? C29 C30 1.481(5) . ? C30 C31 1.390(5) . ? C30 C35 1.393(5) . ? C31 C32 1.385(6) . ? C31 H31 0.9500 . ? C32 C33 1.364(7) . ? C32 H32 0.9500 . ? C33 C34 1.381(7) . ? C33 H33 0.9500 . ? C34 C35 1.384(6) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C37 1.506(5) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 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 O3 167.45(10) . . ? N2 Ni1 O1 88.19(10) . . ? O3 Ni1 O1 92.91(9) . . ? N2 Ni1 O2 88.13(10) . . ? O3 Ni1 O2 79.71(9) . . ? O1 Ni1 O2 81.05(9) . . ? N2 Ni1 N4 105.46(10) . . ? O3 Ni1 N4 86.48(10) . . ? O1 Ni1 N4 103.01(10) . . ? O2 Ni1 N4 165.82(9) . . ? N2 Ni1 N3 81.93(10) . . ? O3 Ni1 N3 96.82(10) . . ? O1 Ni1 N3 170.12(10) . . ? O2 Ni1 N3 98.95(10) . . ? N4 Ni1 N3 79.40(10) . . ? O6 Cl1 O4 110.97(19) . . ? O6 Cl1 O7 109.48(18) . . ? O4 Cl1 O7 110.22(19) . . ? O6 Cl1 O5 107.96(19) . . ? O4 Cl1 O5 109.67(18) . . ? O7 Cl1 O5 108.48(18) . . ? O11 Cl2 O8 110.1(3) . . ? O11 Cl2 O9 110.4(2) . . ? O8 Cl2 O9 109.6(2) . . ? O11 Cl2 O10 108.8(2) . . ? O8 Cl2 O10 108.3(2) . . ? O9 Cl2 O10 109.66(17) . . ? C5 O1 Ni1 124.3(2) . . ? N6 O2 Ni1 107.27(18) . . ? N6 O2 H2 108(4) . . ? Ni1 O2 H2 113(4) . . ? C36 O3 Ni1 112.5(2) . . ? C38 O12 H12 109.5 . . ? C5 N1 C6 130.8(3) . . ? C5 N1 H1N 114(3) . . ? C6 N1 H1N 115(3) . . ? C6 N2 C10 119.2(3) . . ? C6 N2 Ni1 125.1(2) . . ? C10 N2 Ni1 114.0(2) . . ? C12 N3 C11 110.8(2) . . ? C12 N3 C24 106.8(2) . . ? C11 N3 C24 111.4(2) . . ? C12 N3 Ni1 103.88(18) . . ? C11 N3 Ni1 103.11(18) . . ? C24 N3 Ni1 120.5(2) . . ? C13 N4 C17 118.5(3) . . ? C13 N4 Ni1 108.6(2) . . ? C17 N4 Ni1 130.0(2) . . ? C29 N5 C25 120.2(3) . . ? C36 N6 O2 118.1(3) . . ? C36 N6 H6N 132(2) . . ? O2 N6 H6N 109(2) . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C2 108.9(3) . . ? C5 C4 C1 111.5(3) . . ? C2 C4 C1 109.9(4) . . ? C5 C4 C3 107.5(3) . . ? C2 C4 C3 108.4(4) . . ? C1 C4 C3 110.6(4) . . ? O1 C5 N1 123.3(3) . . ? O1 C5 C4 121.0(3) . . ? N1 C5 C4 115.6(3) . . ? N2 C6 N1 119.9(3) . . ? N2 C6 C7 121.7(3) . . ? N1 C6 C7 118.4(3) . . ? C8 C7 C6 118.4(3) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 118.6(3) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? N2 C10 C9 121.9(3) . . ? N2 C10 C11 114.1(3) . . ? C9 C10 C11 124.0(3) . . ? N3 C11 C10 110.0(3) . . ? N3 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N3 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N3 C12 C13 112.0(3) . . ? N3 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N3 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? N4 C13 C14 122.4(3) . . ? N4 C13 C12 118.2(3) . . ? C14 C13 C12 119.3(3) . . ? C15 C14 C13 119.0(3) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 119.1(3) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C15 C16 C17 120.2(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? N4 C17 C16 120.7(3) . . ? N4 C17 C18 119.2(3) . . ? C16 C17 C18 120.1(3) . . ? C23 C18 C19 119.0(3) . . ? C23 C18 C17 120.4(3) . . ? C19 C18 C17 120.6(3) . . ? C20 C19 C18 120.6(3) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C21 C20 C19 119.9(3) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C20 119.6(4) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C23 120.9(4) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C22 C23 C18 119.9(3) . . ? C22 C23 H23 120.0 . . ? C18 C23 H23 120.0 . . ? N3 C24 C25 114.9(3) . . ? N3 C24 H24A 108.6 . . ? C25 C24 H24A 108.6 . . ? N3 C24 H24B 108.6 . . ? C25 C24 H24B 108.6 . . ? H24A C24 H24B 107.5 . . ? N5 C25 C26 121.3(3) . . ? N5 C25 C24 116.8(3) . . ? C26 C25 C24 121.9(3) . . ? C27 C26 C25 119.4(3) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C26 C27 C28 119.2(3) . . ? C26 C27 H27 120.4 . . ? C28 C27 H27 120.4 . . ? C27 C28 C29 119.5(3) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? N5 C29 C28 120.3(3) . . ? N5 C29 C30 117.8(3) . . ? C28 C29 C30 121.9(3) . . ? C31 C30 C35 119.2(4) . . ? C31 C30 C29 119.5(3) . . ? C35 C30 C29 121.3(3) . . ? C32 C31 C30 120.5(4) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C33 C32 C31 119.6(4) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C32 C33 C34 121.1(4) . . ? C32 C33 H33 119.5 . . ? C34 C33 H33 119.5 . . ? C33 C34 C35 119.7(4) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C30 119.9(4) . . ? C34 C35 H35 120.0 . . ? C30 C35 H35 120.0 . . ? O3 C36 N6 121.4(3) . . ? O3 C36 C37 121.9(3) . . ? N6 C36 C37 116.8(3) . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O12 C38 H38A 109.5 . . ? O12 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O12 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 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 O1 C5 -31.1(3) . . . . ? O3 Ni1 O1 C5 136.4(3) . . . . ? O2 Ni1 O1 C5 57.3(3) . . . . ? N4 Ni1 O1 C5 -136.5(3) . . . . ? N3 Ni1 O1 C5 -33.4(7) . . . . ? N2 Ni1 O2 N6 175.5(2) . . . . ? O3 Ni1 O2 N6 -7.59(19) . . . . ? O1 Ni1 O2 N6 87.05(19) . . . . ? N4 Ni1 O2 N6 -20.8(5) . . . . ? N3 Ni1 O2 N6 -102.95(19) . . . . ? N2 Ni1 O3 C36 23.5(6) . . . . ? O1 Ni1 O3 C36 -71.3(2) . . . . ? O2 Ni1 O3 C36 9.1(2) . . . . ? N4 Ni1 O3 C36 -174.1(2) . . . . ? N3 Ni1 O3 C36 107.0(2) . . . . ? O3 Ni1 N2 C6 -70.5(6) . . . . ? O1 Ni1 N2 C6 24.8(3) . . . . ? O2 Ni1 N2 C6 -56.3(3) . . . . ? N4 Ni1 N2 C6 127.8(3) . . . . ? N3 Ni1 N2 C6 -155.6(3) . . . . ? O3 Ni1 N2 C10 94.2(5) . . . . ? O1 Ni1 N2 C10 -170.5(2) . . . . ? O2 Ni1 N2 C10 108.4(2) . . . . ? N4 Ni1 N2 C10 -67.5(2) . . . . ? N3 Ni1 N2 C10 9.0(2) . . . . ? N2 Ni1 N3 C12 -144.0(2) . . . . ? O3 Ni1 N3 C12 48.6(2) . . . . ? O1 Ni1 N3 C12 -141.6(5) . . . . ? O2 Ni1 N3 C12 129.15(19) . . . . ? N4 Ni1 N3 C12 -36.55(19) . . . . ? N2 Ni1 N3 C11 -28.36(18) . . . . ? O3 Ni1 N3 C11 164.23(18) . . . . ? O1 Ni1 N3 C11 -26.0(7) . . . . ? O2 Ni1 N3 C11 -115.17(18) . . . . ? N4 Ni1 N3 C11 79.12(19) . . . . ? N2 Ni1 N3 C24 96.6(2) . . . . ? O3 Ni1 N3 C24 -70.9(2) . . . . ? O1 Ni1 N3 C24 99.0(6) . . . . ? O2 Ni1 N3 C24 9.7(2) . . . . ? N4 Ni1 N3 C24 -156.0(2) . . . . ? N2 Ni1 N4 C13 109.5(2) . . . . ? O3 Ni1 N4 C13 -66.6(2) . . . . ? O1 Ni1 N4 C13 -158.7(2) . . . . ? O2 Ni1 N4 C13 -53.5(5) . . . . ? N3 Ni1 N4 C13 31.0(2) . . . . ? N2 Ni1 N4 C17 -90.7(3) . . . . ? O3 Ni1 N4 C17 93.2(3) . . . . ? O1 Ni1 N4 C17 1.1(3) . . . . ? O2 Ni1 N4 C17 106.3(4) . . . . ? N3 Ni1 N4 C17 -169.2(3) . . . . ? Ni1 O2 N6 C36 5.8(3) . . . . ? Ni1 O1 C5 N1 25.9(5) . . . . ? Ni1 O1 C5 C4 -151.1(3) . . . . ? C6 N1 C5 O1 -3.1(6) . . . . ? C6 N1 C5 C4 174.0(3) . . . . ? C2 C4 C5 O1 -3.8(5) . . . . ? C1 C4 C5 O1 -125.2(4) . . . . ? C3 C4 C5 O1 113.4(4) . . . . ? C2 C4 C5 N1 179.0(4) . . . . ? C1 C4 C5 N1 57.6(5) . . . . ? C3 C4 C5 N1 -63.8(4) . . . . ? C10 N2 C6 N1 -177.7(3) . . . . ? Ni1 N2 C6 N1 -13.8(4) . . . . ? C10 N2 C6 C7 0.0(5) . . . . ? Ni1 N2 C6 C7 163.9(3) . . . . ? C5 N1 C6 N2 -3.6(5) . . . . ? C5 N1 C6 C7 178.6(3) . . . . ? N2 C6 C7 C8 0.2(5) . . . . ? N1 C6 C7 C8 177.9(3) . . . . ? C6 C7 C8 C9 0.5(5) . . . . ? C7 C8 C9 C10 -1.3(5) . . . . ? C6 N2 C10 C9 -0.9(5) . . . . ? Ni1 N2 C10 C9 -166.5(3) . . . . ? C6 N2 C10 C11 179.4(3) . . . . ? Ni1 N2 C10 C11 13.8(3) . . . . ? C8 C9 C10 N2 1.6(5) . . . . ? C8 C9 C10 C11 -178.7(3) . . . . ? C12 N3 C11 C10 153.5(3) . . . . ? C24 N3 C11 C10 -87.7(3) . . . . ? Ni1 N3 C11 C10 42.9(3) . . . . ? N2 C10 C11 N3 -39.9(4) . . . . ? C9 C10 C11 N3 140.4(3) . . . . ? C11 N3 C12 C13 -72.6(3) . . . . ? C24 N3 C12 C13 165.8(3) . . . . ? Ni1 N3 C12 C13 37.5(3) . . . . ? C17 N4 C13 C14 -1.9(5) . . . . ? Ni1 N4 C13 C14 160.6(3) . . . . ? C17 N4 C13 C12 179.2(3) . . . . ? Ni1 N4 C13 C12 -18.3(3) . . . . ? N3 C12 C13 N4 -13.9(4) . . . . ? N3 C12 C13 C14 167.2(3) . . . . ? N4 C13 C14 C15 -1.2(5) . . . . ? C12 C13 C14 C15 177.6(3) . . . . ? C13 C14 C15 C16 2.4(5) . . . . ? C14 C15 C16 C17 -0.4(5) . . . . ? C13 N4 C17 C16 3.8(5) . . . . ? Ni1 N4 C17 C16 -154.3(3) . . . . ? C13 N4 C17 C18 -173.7(3) . . . . ? Ni1 N4 C17 C18 28.2(4) . . . . ? C15 C16 C17 N4 -2.7(5) . . . . ? C15 C16 C17 C18 174.7(3) . . . . ? N4 C17 C18 C23 -143.0(3) . . . . ? C16 C17 C18 C23 39.5(5) . . . . ? N4 C17 C18 C19 40.3(4) . . . . ? C16 C17 C18 C19 -137.2(3) . . . . ? C23 C18 C19 C20 2.1(5) . . . . ? C17 C18 C19 C20 178.8(3) . . . . ? C18 C19 C20 C21 -1.9(5) . . . . ? C19 C20 C21 C22 0.5(5) . . . . ? C20 C21 C22 C23 0.7(6) . . . . ? C21 C22 C23 C18 -0.5(6) . . . . ? C19 C18 C23 C22 -0.9(5) . . . . ? C17 C18 C23 C22 -177.7(3) . . . . ? C12 N3 C24 C25 168.9(3) . . . . ? C11 N3 C24 C25 47.7(4) . . . . ? Ni1 N3 C24 C25 -73.2(3) . . . . ? C29 N5 C25 C26 2.4(5) . . . . ? C29 N5 C25 C24 -178.3(3) . . . . ? N3 C24 C25 N5 77.9(4) . . . . ? N3 C24 C25 C26 -102.7(4) . . . . ? N5 C25 C26 C27 -2.0(5) . . . . ? C24 C25 C26 C27 178.7(3) . . . . ? C25 C26 C27 C28 0.7(5) . . . . ? C26 C27 C28 C29 0.2(6) . . . . ? C25 N5 C29 C28 -1.4(5) . . . . ? C25 N5 C29 C30 -179.6(3) . . . . ? C27 C28 C29 N5 0.1(5) . . . . ? C27 C28 C29 C30 178.2(3) . . . . ? N5 C29 C30 C31 -142.4(3) . . . . ? C28 C29 C30 C31 39.5(5) . . . . ? N5 C29 C30 C35 37.9(5) . . . . ? C28 C29 C30 C35 -140.3(4) . . . . ? C35 C30 C31 C32 -0.8(6) . . . . ? C29 C30 C31 C32 179.5(4) . . . . ? C30 C31 C32 C33 0.1(7) . . . . ? C31 C32 C33 C34 0.3(7) . . . . ? C32 C33 C34 C35 0.0(7) . . . . ? C33 C34 C35 C30 -0.7(7) . . . . ? C31 C30 C35 C34 1.1(6) . . . . ? C29 C30 C35 C34 -179.2(4) . . . . ? Ni1 O3 C36 N6 -9.0(4) . . . . ? Ni1 O3 C36 C37 170.8(3) . . . . ? O2 N6 C36 O3 2.0(5) . . . . ? O2 N6 C36 C37 -177.9(3) . . . . ? 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 O12 H12 O10 0.84 2.21 2.880(5) 136.5 . N6 H6N O5 0.94(4) 1.94(4) 2.845(4) 160(3) 6_565 N1 H1N O12 0.867(19) 2.20(2) 3.040(4) 162(4) 1_554 O2 H2 N5 0.838(19) 1.72(3) 2.518(3) 158(5) . _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.680 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.079