Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2002 data_global #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ _journal_coden_Cambridge 186 _publ_requested_journal ' Dalton Transactions' _publ_contact_author 'Ronald R. Fenton' _publ_contact_author_address ; Ronald R. Fenton School of Chemistry University of Sydney Sydney, NSW. Australia 2006. ; _publ_contact_author_phone ' +61 2 9351 2781 ' _publ_contact_author_fax ' +61 2 9351 3329 ' _publ_contact_author_email ' r.fenton@chem.usyd.edu.su ' loop_ _publ_author_name _publ_author_address ' Colin L. Weeks' ; School of Chemistry University of Sydney Sydney, NSW. Australia 2006. ; 'Peter Turner' ; School of Chemistry University of Sydney Sydney, NSW. Australia 2006. ; 'Ronald R. Fenton' ; School of Chemistry University of Sydney Sydney, NSW. Australia 2006. ; 'Peter A. Lay' ; School of Chemistry University of Sydney Sydney, NSW. Australia 2006. ; _publ_section_title ; Nickel(II) complexes with amide ligands: oxidative dehydrogenation of the amines in a tetradentate diamide-diamine ligand ; data_rrf2 _database_code_CSD 169589 _audit_creation_date '1998-07-26' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; DIRDIF92 PATTY (Beurskens, 1992) ; _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 9.748(1) _cell_length_b 9.923(1) _cell_length_c 8.383(1) _cell_angle_alpha 105.53(1) _cell_angle_beta 104.40(1) _cell_angle_gamma 112.37(1) _cell_volume 664.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 47.1 _cell_measurement_theta_max 58.7 #------------------------------------------------------------------------------ _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 325.00 _chemical_formula_analytical ? _chemical_formula_sum 'C12 H18 N4 Ni1 O3 ' _chemical_formula_moiety '?' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 340.00 _exptl_absorpt_coefficient_mu 2.245 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.844 _exptl_special_details ; The scan width was (1.73+0.35tan\q)\% with an \w scan speed of 16\% per minute (up to 11 scans to achieve I/\s(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 2.71 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 2396 _reflns_number_total 2250 _reflns_number_observed 1911 _reflns_observed_criterion >3.00\s(I) _diffrn_reflns_av_R_equivalents 0.10124 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.34 _diffrn_reflns_theta_max 65.07 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.11794 _diffrn_orient_matrix_UB_12 0.03398 _diffrn_orient_matrix_UB_13 0.04909 _diffrn_orient_matrix_UB_21 0.02552 _diffrn_orient_matrix_UB_22 0.11345 _diffrn_orient_matrix_UB_23 0.02828 _diffrn_orient_matrix_UB_31 -0.00096 _diffrn_orient_matrix_UB_32 0.01322 _diffrn_orient_matrix_UB_33 0.12217 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 24 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 36 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Ni 0 2 -3.003 0.509 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 6 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Ni(1) 0.15546(7) 0.14946(7) 0.25811(8) 0.0373(2) 1.000 . Uani d ? O(1) -0.1728(4) -0.2759(3) 0.1634(4) 0.0574(9) 1.000 . Uani d ? O(2) 0.5298(4) 0.2486(4) 0.1261(4) 0.0598(9) 1.000 . Uani d ? O(3) 0.8344(5) 0.4410(5) 0.1350(7) 0.079(1) 1.000 . Uani d ? N(1) -0.0177(4) 0.1377(3) 0.3280(4) 0.0388(8) 1.000 . Uani d ? N(2) 0.0634(4) -0.0652(3) 0.2025(4) 0.0404(8) 1.000 . Uani d ? N(3) 0.3043(4) 0.1200(4) 0.1785(4) 0.0442(9) 1.000 . Uani d ? N(4) 0.2729(4) 0.3629(3) 0.2865(4) 0.0400(8) 1.000 . Uani d ? C(1) -0.0709(5) 0.2512(5) 0.4063(5) 0.046(1) 1.000 . Uani d ? C(2) -0.2321(5) 0.1494(5) 0.4103(6) 0.055(1) 1.000 . Uani d ? C(3) -0.2622(5) -0.0228(5) 0.3343(6) 0.048(1) 1.000 . Uani d ? C(4) -0.1195(4) -0.0049(4) 0.2936(5) 0.041(1) 1.000 . Uani d ? C(5) -0.0789(5) -0.1322(4) 0.2121(5) 0.0402(10) 1.000 . Uani d ? C(6) 0.1289(5) -0.1551(4) 0.1082(5) 0.043(1) 1.000 . Uani d ? C(7) 0.2980(5) -0.0360(5) 0.1429(6) 0.049(1) 1.000 . Uani d ? C(8) 0.4169(5) 0.2413(5) 0.1704(5) 0.043(1) 1.000 . Uani d ? C(9) 0.3894(5) 0.3843(4) 0.2333(5) 0.0417(10) 1.000 . Uani d ? C(10) 0.4786(5) 0.5456(5) 0.2396(6) 0.050(1) 1.000 . Uani d ? C(11) 0.3991(5) 0.6349(5) 0.3253(6) 0.051(1) 1.000 . Uani d ? C(12) 0.2586(5) 0.5085(5) 0.3409(6) 0.048(1) 1.000 . Uani d ? H(1a) 0.0055 0.3247 0.5247 0.056 1.000 . Uiso c ? H(1b) -0.0840 0.3077 0.3335 0.056 1.000 . Uiso c ? H(2a) -0.3157 0.1603 0.3377 0.066 1.000 . Uiso c ? H(2b) -0.2264 0.1798 0.5303 0.066 1.000 . Uiso c ? H(3a) -0.3585 -0.0874 0.2285 0.058 1.000 . Uiso c ? H(3b) -0.2684 -0.0676 0.4209 0.058 1.000 . Uiso c ? H(3Oa) 0.834(6) 0.535(7) 0.126(7) 0.08(2) 1.000 . Uiso d ? H(3Ob) 0.749(7) 0.397(7) 0.132(8) 0.09(2) 1.000 . Uiso d ? H(6a) 0.1320 -0.2326 0.1532 0.052 1.000 . Uiso c ? H(6b) 0.0642 -0.2065 -0.0173 0.052 1.000 . Uiso c ? H(7a) 0.3220 -0.0673 0.0403 0.059 1.000 . Uiso c ? H(7b) 0.3739 -0.0304 0.2443 0.059 1.000 . Uiso c ? H(10a) 0.5903 0.5936 0.3119 0.061 1.000 . Uiso c ? H(10b) 0.4651 0.5422 0.1221 0.061 1.000 . Uiso c ? H(11a) 0.4736 0.7162 0.4408 0.062 1.000 . Uiso c ? H(11b) 0.3608 0.6809 0.2508 0.062 1.000 . Uiso c ? H(12a) 0.1586 0.4916 0.2634 0.058 1.000 . Uiso c ? H(12b) 0.2660 0.5406 0.4615 0.058 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Ni(1) 0.0391(4) 0.0246(4) 0.0439(4) 0.0173(3) 0.0113(3) 0.0086(3) O(1) 0.058(2) 0.029(2) 0.079(2) 0.018(1) 0.026(2) 0.018(1) O(2) 0.054(2) 0.050(2) 0.084(2) 0.028(1) 0.037(2) 0.024(2) O(3) 0.066(2) 0.050(2) 0.128(3) 0.035(2) 0.035(2) 0.036(2) N(1) 0.043(2) 0.027(2) 0.045(2) 0.018(1) 0.012(1) 0.012(1) N(2) 0.043(2) 0.027(2) 0.048(2) 0.021(1) 0.012(1) 0.009(1) N(3) 0.043(2) 0.033(2) 0.057(2) 0.022(1) 0.019(2) 0.014(2) N(4) 0.039(2) 0.024(2) 0.047(2) 0.015(1) 0.010(1) 0.008(1) C(1) 0.054(2) 0.033(2) 0.051(2) 0.027(2) 0.018(2) 0.009(2) C(2) 0.063(3) 0.051(3) 0.070(3) 0.037(2) 0.035(2) 0.029(2) C(3) 0.047(2) 0.044(2) 0.055(2) 0.023(2) 0.021(2) 0.020(2) C(4) 0.045(2) 0.035(2) 0.042(2) 0.022(2) 0.010(2) 0.016(2) C(5) 0.048(2) 0.028(2) 0.041(2) 0.020(2) 0.009(2) 0.013(2) C(6) 0.049(2) 0.031(2) 0.048(2) 0.024(2) 0.013(2) 0.010(2) C(7) 0.049(2) 0.037(2) 0.064(3) 0.028(2) 0.020(2) 0.014(2) C(8) 0.043(2) 0.034(2) 0.044(2) 0.020(2) 0.010(2) 0.009(2) C(9) 0.044(2) 0.028(2) 0.042(2) 0.016(2) 0.006(2) 0.008(2) C(10) 0.050(2) 0.035(2) 0.062(2) 0.017(2) 0.025(2) 0.017(2) C(11) 0.058(3) 0.032(2) 0.060(3) 0.021(2) 0.021(2) 0.015(2) C(12) 0.050(2) 0.030(2) 0.060(2) 0.020(2) 0.020(2) 0.012(2) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000032(6) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1911 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_obs 0.0507 _refine_ls_wR_factor_all 0.0599 _refine_ls_wR_factor_obs 0.0599 _refine_ls_goodness_of_fit_all 3.325 _refine_ls_goodness_of_fit_obs 3.325 _refine_ls_shift/esd_max 0.0280 _refine_ls_shift/esd_mean 0.0030 _refine_diff_density_min -0.67 _refine_diff_density_max 0.97 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni(1) N(1) 1.893(3) . . yes Ni(1) N(2) 1.834(3) . . yes Ni(1) N(3) 1.827(3) . . yes Ni(1) N(4) 1.898(3) . . yes O(1) C(5) 1.243(4) . . yes O(2) C(8) 1.230(5) . . yes O(3) H(3Oa) 0.95(6) . . no O(3) H(3Ob) 0.77(5) . . no N(1) C(1) 1.478(4) . . yes N(1) C(4) 1.281(5) . . yes N(2) C(5) 1.325(5) . . yes N(2) C(6) 1.461(4) . . yes N(3) C(7) 1.470(5) . . yes N(3) C(8) 1.316(5) . . yes N(4) C(9) 1.285(5) . . yes N(4) C(12) 1.466(4) . . yes C(1) C(2) 1.526(6) . . yes C(1) H(1a) 0.95 . . no C(1) H(1b) 0.95 . . no C(2) C(3) 1.534(6) . . yes C(2) H(2a) 0.95 . . no C(2) H(2b) 0.95 . . no C(3) C(4) 1.470(5) . . yes C(3) H(3a) 0.95 . . no C(3) H(3b) 0.95 . . no C(4) C(5) 1.508(5) . . yes C(6) C(7) 1.515(6) . . yes C(6) H(6a) 0.95 . . no C(6) H(6b) 0.95 . . no C(7) H(7a) 0.95 . . no C(7) H(7b) 0.95 . . no C(8) C(9) 1.524(5) . . yes C(9) C(10) 1.481(6) . . yes C(10) C(11) 1.537(6) . . yes C(10) H(10a) 0.95 . . no C(10) H(10b) 0.95 . . no C(11) C(12) 1.528(6) . . yes C(11) H(11a) 0.95 . . no C(11) H(11b) 0.95 . . no C(12) H(12a) 0.95 . . no C(12) H(12b) 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N(1) Ni(1) N(2) 84.5(1) . . . yes N(1) Ni(1) N(3) 169.1(1) . . . yes N(1) Ni(1) N(4) 106.5(1) . . . yes N(2) Ni(1) N(3) 84.7(1) . . . yes N(2) Ni(1) N(4) 168.5(1) . . . yes N(3) Ni(1) N(4) 84.3(1) . . . yes H(3Oa) O(3) H(3Ob) 100(4) . . . no Ni(1) N(1) C(1) 136.3(3) . . . yes Ni(1) N(1) C(4) 113.2(3) . . . yes C(1) N(1) C(4) 110.4(3) . . . yes Ni(1) N(2) C(5) 116.7(2) . . . yes Ni(1) N(2) C(6) 117.7(3) . . . yes C(5) N(2) C(6) 123.6(3) . . . yes Ni(1) N(3) C(7) 116.7(3) . . . yes Ni(1) N(3) C(8) 118.8(3) . . . yes C(7) N(3) C(8) 124.2(3) . . . yes Ni(1) N(4) C(9) 112.6(2) . . . yes Ni(1) N(4) C(12) 136.5(3) . . . yes C(9) N(4) C(12) 110.7(3) . . . yes N(1) C(1) C(2) 105.5(3) . . . yes N(1) C(1) H(1a) 110.5 . . . no N(1) C(1) H(1b) 110.5 . . . no C(2) C(1) H(1a) 110.5 . . . no C(2) C(1) H(1b) 110.5 . . . no H(1a) C(1) H(1b) 109.5 . . . no C(1) C(2) C(3) 105.6(3) . . . yes C(1) C(2) H(2a) 110.4 . . . no C(1) C(2) H(2b) 110.4 . . . no C(3) C(2) H(2a) 110.4 . . . no C(3) C(2) H(2b) 110.4 . . . no H(2a) C(2) H(2b) 109.5 . . . no C(2) C(3) C(4) 102.8(3) . . . yes C(2) C(3) H(3a) 111.1 . . . no C(2) C(3) H(3b) 111.1 . . . no C(4) C(3) H(3a) 111.1 . . . no C(4) C(3) H(3b) 111.1 . . . no H(3a) C(3) H(3b) 109.5 . . . no N(1) C(4) C(3) 115.7(4) . . . yes N(1) C(4) C(5) 115.5(4) . . . yes C(3) C(4) C(5) 128.8(3) . . . yes O(1) C(5) N(2) 129.0(4) . . . yes O(1) C(5) C(4) 121.4(4) . . . yes N(2) C(5) C(4) 109.6(3) . . . yes N(2) C(6) C(7) 106.8(3) . . . yes N(2) C(6) H(6a) 110.2 . . . no N(2) C(6) H(6b) 110.2 . . . no C(7) C(6) H(6a) 110.1 . . . no C(7) C(6) H(6b) 110.1 . . . no H(6a) C(6) H(6b) 109.5 . . . no N(3) C(7) C(6) 107.7(3) . . . yes N(3) C(7) H(7a) 109.9 . . . no N(3) C(7) H(7b) 109.9 . . . no C(6) C(7) H(7a) 109.9 . . . no C(6) C(7) H(7b) 109.9 . . . no H(7a) C(7) H(7b) 109.5 . . . no O(2) C(8) N(3) 129.3(4) . . . yes O(2) C(8) C(9) 122.7(4) . . . yes N(3) C(8) C(9) 107.9(3) . . . yes N(4) C(9) C(8) 116.3(3) . . . yes N(4) C(9) C(10) 115.3(3) . . . yes C(8) C(9) C(10) 128.4(4) . . . yes C(9) C(10) C(11) 102.6(3) . . . yes C(9) C(10) H(10a) 111.2 . . . no C(9) C(10) H(10b) 111.2 . . . no C(11) C(10) H(10a) 111.2 . . . no C(11) C(10) H(10b) 111.2 . . . no H(10a) C(10) H(10b) 109.5 . . . no C(10) C(11) C(12) 105.2(3) . . . yes C(10) C(11) H(11a) 110.5 . . . no C(10) C(11) H(11b) 110.5 . . . no C(12) C(11) H(11a) 110.5 . . . no C(12) C(11) H(11b) 110.5 . . . no H(11a) C(11) H(11b) 109.5 . . . no N(4) C(12) C(11) 105.9(3) . . . yes N(4) C(12) H(12a) 110.4 . . . no N(4) C(12) H(12b) 110.4 . . . no C(11) C(12) H(12a) 110.4 . . . no C(11) C(12) H(12b) 110.4 . . . no H(12a) C(12) H(12b) 109.5 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) O(3) 2.784(4) . 1_445 no O(1) C(9) 3.089(5) . 2 no O(1) C(8) 3.381(5) . 2 no O(1) C(10) 3.397(5) . 2 no O(1) N(4) 3.422(4) . 2 no O(1) C(10) 3.493(5) . 1_445 no O(2) O(3) 2.822(5) . . no O(2) C(2) 3.504(6) . 1_655 no O(2) C(3) 3.555(5) . 2 no O(3) C(6) 3.220(5) . 2_655 no O(3) C(1) 3.486(6) . 1_655 no O(3) C(7) 3.576(5) . 2_655 no N(2) C(3) 3.571(5) . 2_556 no N(3) C(5) 3.522(5) . 2 no N(3) C(4) 3.561(5) . 2 no C(5) C(8) 3.533(5) . 2 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Ni(1) N(1) C(1) C(2) . . . . 175.4(3) no Ni(1) N(1) C(4) C(3) . . . . -176.3(3) no Ni(1) N(1) C(4) C(5) . . . . 2.1(4) no Ni(1) N(2) C(5) O(1) . . . . 171.5(3) no Ni(1) N(2) C(5) C(4) . . . . -7.8(4) no Ni(1) N(2) C(6) C(7) . . . . 21.4(4) no Ni(1) N(3) C(7) C(6) . . . . 23.1(4) no Ni(1) N(3) C(8) O(2) . . . . 177.8(3) no Ni(1) N(3) C(8) C(9) . . . . -0.4(4) no Ni(1) N(4) C(9) C(8) . . . . -3.6(4) no Ni(1) N(4) C(9) C(10) . . . . 175.8(3) no Ni(1) N(4) C(12) C(11) . . . . -178.3(3) no O(1) C(5) N(2) C(6) . . . . 8.0(6) no O(1) C(5) C(4) N(1) . . . . -175.9(4) no O(1) C(5) C(4) C(3) . . . . 2.3(6) no O(2) C(8) N(3) C(7) . . . . 3.6(7) no O(2) C(8) C(9) N(4) . . . . -175.7(4) no O(2) C(8) C(9) C(10) . . . . 5.1(6) no N(1) Ni(1) N(2) C(5) . . . . 7.5(3) no N(1) Ni(1) N(2) C(6) . . . . 172.0(3) no N(1) Ni(1) N(3) C(7) . . . . -11.9(9) no N(1) Ni(1) N(3) C(8) . . . . 173.4(6) no N(1) Ni(1) N(4) C(9) . . . . -176.3(3) no N(1) Ni(1) N(4) C(12) . . . . -2.1(4) no N(1) C(1) C(2) C(3) . . . . 1.0(4) no N(1) C(4) C(3) C(2) . . . . -0.7(5) no N(1) C(4) C(5) N(2) . . . . 3.5(5) no N(2) Ni(1) N(1) C(1) . . . . 178.1(4) no N(2) Ni(1) N(1) C(4) . . . . -5.1(3) no N(2) Ni(1) N(3) C(7) . . . . -9.6(3) no N(2) Ni(1) N(3) C(8) . . . . 175.7(3) no N(2) Ni(1) N(4) C(9) . . . . -13.7(8) no N(2) Ni(1) N(4) C(12) . . . . 160.5(6) no N(2) C(5) C(4) C(3) . . . . -178.3(4) no N(2) C(6) C(7) N(3) . . . . -26.2(4) no N(3) Ni(1) N(1) C(1) . . . . -179.6(6) no N(3) Ni(1) N(1) C(4) . . . . -2.8(9) no N(3) Ni(1) N(2) C(5) . . . . -172.1(3) no N(3) Ni(1) N(2) C(6) . . . . -7.6(3) no N(3) Ni(1) N(4) C(9) . . . . 2.6(3) no N(3) Ni(1) N(4) C(12) . . . . 176.8(4) no N(3) C(8) C(9) N(4) . . . . 2.7(5) no N(3) C(8) C(9) C(10) . . . . -176.5(4) no N(4) Ni(1) N(1) C(1) . . . . -5.3(4) no N(4) Ni(1) N(1) C(4) . . . . 171.5(3) no N(4) Ni(1) N(2) C(5) . . . . -155.8(6) no N(4) Ni(1) N(2) C(6) . . . . 8.7(8) no N(4) Ni(1) N(3) C(7) . . . . 173.6(3) no N(4) Ni(1) N(3) C(8) . . . . -1.1(3) no N(4) C(9) C(10) C(11) . . . . 3.9(5) no N(4) C(12) C(11) C(10) . . . . 6.2(4) no C(1) N(1) C(4) C(3) . . . . 1.3(5) no C(1) N(1) C(4) C(5) . . . . 179.8(3) no C(1) C(2) C(3) C(4) . . . . -0.3(4) no C(2) C(1) N(1) C(4) . . . . -1.4(4) no C(2) C(3) C(4) C(5) . . . . -178.8(3) no C(4) C(5) N(2) C(6) . . . . -171.3(3) no C(5) N(2) C(6) C(7) . . . . -175.3(3) no C(6) C(7) N(3) C(8) . . . . -162.5(4) no C(7) N(3) C(8) C(9) . . . . -174.7(3) no C(8) C(9) N(4) C(12) . . . . -179.3(3) no C(8) C(9) C(10) C(11) . . . . -176.9(4) no C(9) N(4) C(12) C(11) . . . . -4.1(4) no C(9) C(10) C(11) C(12) . . . . -5.9(4) no C(10) C(9) N(4) C(12) . . . . 0.1(5) no #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A 'O(3)' 'H(3Oa)' 'O(1)' '0.95(6)' '1.85(6)' '2.784(4)' '165(4)' '1_665' 'O(3)' 'H(3Ob)' 'O(2)' '0.77' '2.06' '2.822(5)' '170.9' '.' #===END data_rrf4 _database_code_CSD 169590 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H32 N4 Ni O5' _chemical_formula_weight 419.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.0175(3) _cell_length_b 10.1232(3) _cell_length_c 21.1448(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1930.22(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 0 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour 'orange-yellow' _exptl_crystal_size_max 0.226 _exptl_crystal_size_mid 0.224 _exptl_crystal_size_min 0.160 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.039 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 75 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 20641 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4587 _reflns_number_gt 4221 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINT _computing_data_reduction 'SAINT and XPREP' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'teXsan for Windows (MSC, 1997)' _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^)+(0.0449P)^2^+0.2440P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(12) _refine_ls_number_reflns 4587 _refine_ls_number_parameters 260 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0764 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.89183(3) 0.54894(2) 0.010270(12) 0.03253(8) Uani 1 1 d . . . O1 O 0.7306(2) 0.25708(16) 0.11274(8) 0.0544(5) Uani 1 1 d . . . O2 O 1.02680(19) 0.89303(16) 0.07010(8) 0.0434(4) Uani 1 1 d . . . O3 O 0.5313(3) 0.2293(3) 0.21739(12) 0.0759(7) Uani 1 1 d . . . H3OA H 0.497(5) 0.303(4) 0.230(2) 0.107(16) Uiso 1 1 d . . . H3OB H 0.588(4) 0.247(3) 0.1903(15) 0.066(10) Uiso 1 1 d . . . O4 O 0.7481(2) 0.9824(2) 0.11389(10) 0.0526(5) Uani 1 1 d . . . H4OA H 0.841(4) 0.946(4) 0.1079(17) 0.091(12) Uiso 1 1 d . . . H4OB H 0.745(4) 1.060(4) 0.1149(16) 0.070(11) Uiso 1 1 d . . . O5 O 1.1129(4) 0.5392(3) -0.23762(13) 0.0988(9) Uani 1 1 d D . . H5OA H 1.079(4) 0.457(2) -0.2342(17) 0.082(12) Uiso 1 1 d D . . H5OB H 1.168(4) 0.553(4) -0.2058(15) 0.111(15) Uiso 1 1 d D . . N1 N 0.7775(2) 0.42624(17) -0.03898(9) 0.0377(4) Uani 1 1 d . . . H1N H 0.7024 0.4734 -0.0567 0.045 Uiso 1 1 calc R . . N2 N 0.8263(2) 0.4584(2) 0.08066(8) 0.0368(4) Uani 1 1 d . . . N3 N 0.9730(2) 0.66896(18) 0.06561(8) 0.0353(4) Uani 1 1 d . . . N4 N 0.9824(2) 0.65132(19) -0.05648(8) 0.0354(4) Uani 1 1 d . . . H4N H 1.0618 0.6046 -0.0708 0.042 Uiso 1 1 calc R . . C1 C 0.8476(3) 0.3501(3) -0.09113(11) 0.0452(6) Uani 1 1 d . . . H1A H 0.9518 0.3349 -0.0824 0.054 Uiso 1 1 calc R . . H1B H 0.8388 0.3973 -0.1309 0.054 Uiso 1 1 calc R . . C2 C 0.7636(4) 0.2201(3) -0.09388(12) 0.0533(7) Uani 1 1 d . . . H2A H 0.6707 0.2296 -0.1165 0.064 Uiso 1 1 calc R . . H2B H 0.8224 0.1516 -0.1139 0.064 Uiso 1 1 calc R . . C3 C 0.7374(3) 0.1899(2) -0.02445(12) 0.0497(6) Uani 1 1 d . . . H3A H 0.8244 0.1501 -0.0054 0.060 Uiso 1 1 calc R . . H3B H 0.6535 0.1310 -0.0190 0.060 Uiso 1 1 calc R . . C4 C 0.7056(2) 0.3256(2) 0.00430(11) 0.0411(5) Uani 1 1 d . . . H4A H 0.5982 0.3401 0.0034 0.049 Uiso 1 1 calc R . . C5 C 0.7589(3) 0.3447(2) 0.07220(11) 0.0377(5) Uani 1 1 d . . . C6 C 0.8959(3) 0.5036(2) 0.14037(9) 0.0355(4) Uani 1 1 d . . . H6 H 0.9930 0.4607 0.1436 0.043 Uiso 1 1 calc R . . C7 C 0.8140(3) 0.4796(2) 0.20244(10) 0.0436(5) Uani 1 1 d . . . H7A H 0.7992 0.3856 0.2087 0.052 Uiso 1 1 calc R . . H7B H 0.7175 0.5220 0.2012 0.052 Uiso 1 1 calc R . . C8 C 0.9066(3) 0.5368(3) 0.25696(10) 0.0506(6) Uani 1 1 d . . . H8A H 0.8513 0.5275 0.2961 0.061 Uiso 1 1 calc R . . H8B H 0.9971 0.4857 0.2611 0.061 Uiso 1 1 calc R . . C9 C 0.9467(3) 0.6810(3) 0.24783(11) 0.0563(7) Uani 1 1 d . . . H9A H 1.0124 0.7090 0.2816 0.068 Uiso 1 1 calc R . . H9B H 0.8575 0.7344 0.2500 0.068 Uiso 1 1 calc R . . C10 C 1.0228(3) 0.7027(3) 0.18396(10) 0.0507(6) Uani 1 1 d . . . H10A H 1.0421 0.7961 0.1778 0.061 Uiso 1 1 calc R . . H10B H 1.1168 0.6563 0.1831 0.061 Uiso 1 1 calc R . . C11 C 0.9226(2) 0.6516(2) 0.13146(9) 0.0356(5) Uani 1 1 d . . . H11 H 0.8267 0.6962 0.1356 0.043 Uiso 1 1 calc R . . C12 C 1.0125(2) 0.7842(2) 0.04168(10) 0.0348(5) Uani 1 1 d . . . C13 C 1.0410(3) 0.7788(2) -0.02903(10) 0.0362(5) Uani 1 1 d . . . H13 H 1.1481 0.7832 -0.0365 0.043 Uiso 1 1 calc R . . C14 C 0.9661(4) 0.8885(3) -0.06601(13) 0.0581(7) Uani 1 1 d . . . H14A H 0.8739 0.9150 -0.0461 0.070 Uiso 1 1 calc R . . H14B H 1.0304 0.9649 -0.0697 0.070 Uiso 1 1 calc R . . C15 C 0.9382(3) 0.8270(3) -0.12929(13) 0.0583(7) Uani 1 1 d . . . H15A H 0.8606 0.8736 -0.1519 0.070 Uiso 1 1 calc R . . H15B H 1.0276 0.8268 -0.1549 0.070 Uiso 1 1 calc R . . C16 C 0.8913(3) 0.6897(3) -0.11333(10) 0.0485(6) Uani 1 1 d . . . H16A H 0.9106 0.6304 -0.1484 0.058 Uiso 1 1 calc R . . H16B H 0.7863 0.6869 -0.1035 0.058 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 0.03770(13) 0.02570(12) 0.03419(12) -0.00067(10) 0.00138(10) -0.00348(11) O1 0.0837(13) 0.0309(9) 0.0486(10) 0.0004(7) 0.0158(9) -0.0141(9) O2 0.0495(9) 0.0308(8) 0.0499(9) -0.0041(7) 0.0058(7) -0.0095(7) O3 0.1010(19) 0.0646(16) 0.0621(14) -0.0022(12) 0.0241(13) -0.0091(14) O4 0.0526(11) 0.0349(11) 0.0703(12) -0.0032(9) 0.0083(9) -0.0040(9) O5 0.146(3) 0.0676(17) 0.0824(17) 0.0019(14) -0.0426(18) 0.003(2) N1 0.0427(10) 0.0301(10) 0.0402(9) -0.0018(7) -0.0009(7) -0.0007(8) N2 0.0441(9) 0.0291(9) 0.0371(8) -0.0006(8) 0.0001(7) -0.0030(8) N3 0.0416(10) 0.0303(10) 0.0340(8) -0.0013(7) 0.0024(7) -0.0070(8) N4 0.0384(10) 0.0322(10) 0.0355(9) -0.0023(7) 0.0035(7) -0.0015(8) C1 0.0577(15) 0.0393(13) 0.0386(11) -0.0063(10) 0.0029(10) -0.0008(11) C2 0.0746(18) 0.0374(13) 0.0479(13) -0.0094(11) -0.0023(13) -0.0084(13) C3 0.0649(15) 0.0308(11) 0.0535(15) -0.0054(10) 0.0059(12) -0.0093(11) C4 0.0403(11) 0.0316(10) 0.0513(13) -0.0053(10) 0.0017(10) -0.0044(9) C5 0.0412(11) 0.0270(11) 0.0448(11) -0.0011(9) 0.0073(9) -0.0003(9) C6 0.0418(11) 0.0292(10) 0.0355(10) -0.0004(8) 0.0005(10) 0.0010(10) C7 0.0507(13) 0.0384(13) 0.0419(11) 0.0063(9) 0.0043(10) -0.0037(10) C8 0.0685(16) 0.0480(14) 0.0354(10) 0.0034(10) 0.0017(10) -0.0047(14) C9 0.085(2) 0.0458(15) 0.0380(12) -0.0063(11) 0.0067(13) -0.0115(14) C10 0.0675(16) 0.0472(15) 0.0373(11) -0.0039(10) 0.0017(11) -0.0196(13) C11 0.0417(13) 0.0307(11) 0.0342(10) -0.0023(8) 0.0051(8) -0.0027(9) C12 0.0323(10) 0.0321(11) 0.0398(11) -0.0021(9) 0.0022(8) -0.0052(8) C13 0.0369(10) 0.0329(11) 0.0387(11) 0.0006(9) 0.0016(9) -0.0061(9) C14 0.087(2) 0.0336(13) 0.0538(15) 0.0054(12) -0.0117(14) -0.0035(13) C15 0.0629(17) 0.0552(17) 0.0568(15) 0.0133(13) -0.0071(13) -0.0112(13) C16 0.0577(14) 0.0514(14) 0.0365(10) 0.0053(10) -0.0094(12) -0.0118(14) _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 N3 1.8389(18) . ? Ni1 N2 1.8451(18) . ? Ni1 N1 1.9210(18) . ? Ni1 N4 1.9322(18) . ? O1 C5 1.259(3) . ? O2 C12 1.262(3) . ? O3 H3OA 0.85(4) . ? O3 H3OB 0.79(4) . ? O4 H4OA 0.93(4) . ? O4 H4OB 0.78(4) . ? O5 H5OA 0.894(18) . ? O5 H5OB 0.850(19) . ? N1 C1 1.486(3) . ? N1 C4 1.515(3) . ? N1 H1N 0.9100 . ? N2 C5 1.314(3) . ? N2 C6 1.482(3) . ? N3 C12 1.320(3) . ? N3 C11 1.475(3) . ? N4 C16 1.507(3) . ? N4 C13 1.510(3) . ? N4 H4N 0.9100 . ? C1 C2 1.520(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.518(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.529(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.526(3) . ? C4 H4A 0.9800 . ? C6 C7 1.525(3) . ? C6 C11 1.529(3) . ? C6 H6 0.9800 . ? C7 C8 1.537(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.517(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.531(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.522(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11 0.9800 . ? C12 C13 1.518(3) . ? C13 C14 1.517(3) . ? C13 H13 0.9800 . ? C14 C15 1.497(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.492(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? 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 N3 Ni1 N2 86.70(8) . . ? N3 Ni1 N1 170.36(8) . . ? N2 Ni1 N1 86.80(8) . . ? N3 Ni1 N4 86.68(7) . . ? N2 Ni1 N4 172.34(8) . . ? N1 Ni1 N4 100.24(8) . . ? H3OA O3 H3OB 106(4) . . ? H4OA O4 H4OB 116(4) . . ? H5OA O5 H5OB 107(4) . . ? C1 N1 C4 106.35(17) . . ? C1 N1 Ni1 120.61(15) . . ? C4 N1 Ni1 109.69(13) . . ? C1 N1 H1N 106.5 . . ? C4 N1 H1N 106.5 . . ? Ni1 N1 H1N 106.5 . . ? C5 N2 C6 125.59(19) . . ? C5 N2 Ni1 118.27(15) . . ? C6 N2 Ni1 113.47(14) . . ? C12 N3 C11 123.38(18) . . ? C12 N3 Ni1 116.56(15) . . ? C11 N3 Ni1 113.51(14) . . ? C16 N4 C13 106.08(17) . . ? C16 N4 Ni1 119.39(15) . . ? C13 N4 Ni1 108.99(13) . . ? C16 N4 H4N 107.3 . . ? C13 N4 H4N 107.3 . . ? Ni1 N4 H4N 107.3 . . ? N1 C1 C2 105.4(2) . . ? N1 C1 H1A 110.7 . . ? C2 C1 H1A 110.7 . . ? N1 C1 H1B 110.7 . . ? C2 C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? C3 C2 C1 102.4(2) . . ? C3 C2 H2A 111.3 . . ? C1 C2 H2A 111.3 . . ? C3 C2 H2B 111.3 . . ? C1 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? C2 C3 C4 103.5(2) . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3B 111.1 . . ? C4 C3 H3B 111.1 . . ? H3A C3 H3B 109.0 . . ? N1 C4 C5 110.42(17) . . ? N1 C4 C3 106.48(18) . . ? C5 C4 C3 115.4(2) . . ? N1 C4 H4A 108.1 . . ? C5 C4 H4A 108.1 . . ? C3 C4 H4A 108.1 . . ? O1 C5 N2 128.2(2) . . ? O1 C5 C4 119.2(2) . . ? N2 C5 C4 112.59(19) . . ? N2 C6 C7 118.62(19) . . ? N2 C6 C11 105.32(16) . . ? C7 C6 C11 109.77(18) . . ? N2 C6 H6 107.6 . . ? C7 C6 H6 107.6 . . ? C11 C6 H6 107.6 . . ? C6 C7 C8 108.81(19) . . ? C6 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C9 C8 C7 113.4(2) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 111.0(2) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 109.2(2) . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? N3 C11 C10 117.69(18) . . ? N3 C11 C6 106.36(17) . . ? C10 C11 C6 109.70(19) . . ? N3 C11 H11 107.6 . . ? C10 C11 H11 107.6 . . ? C6 C11 H11 107.6 . . ? O2 C12 N3 128.1(2) . . ? O2 C12 C13 118.9(2) . . ? N3 C12 C13 113.0(2) . . ? N4 C13 C14 105.77(18) . . ? N4 C13 C12 110.51(18) . . ? C14 C13 C12 113.9(2) . . ? N4 C13 H13 108.8 . . ? C14 C13 H13 108.8 . . ? C12 C13 H13 108.8 . . ? C15 C14 C13 103.4(2) . . ? C15 C14 H14A 111.1 . . ? C13 C14 H14A 111.1 . . ? C15 C14 H14B 111.1 . . ? C13 C14 H14B 111.1 . . ? H14A C14 H14B 109.1 . . ? C16 C15 C14 103.5(2) . . ? C16 C15 H15A 111.1 . . ? C14 C15 H15A 111.1 . . ? C16 C15 H15B 111.1 . . ? C14 C15 H15B 111.1 . . ? H15A C15 H15B 109.0 . . ? C15 C16 N4 105.4(2) . . ? C15 C16 H16A 110.7 . . ? N4 C16 H16A 110.7 . . ? C15 C16 H16B 110.7 . . ? N4 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? 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 N3 Ni1 N1 C1 -173.7(4) . . . . ? N2 Ni1 N1 C1 -126.03(18) . . . . ? N4 Ni1 N1 C1 50.91(17) . . . . ? N3 Ni1 N1 C4 -49.7(5) . . . . ? N2 Ni1 N1 C4 -2.03(14) . . . . ? N4 Ni1 N1 C4 174.91(14) . . . . ? N3 Ni1 N2 C5 -175.74(18) . . . . ? N1 Ni1 N2 C5 11.38(18) . . . . ? N4 Ni1 N2 C5 -145.4(6) . . . . ? N3 Ni1 N2 C6 -13.19(16) . . . . ? N1 Ni1 N2 C6 173.94(16) . . . . ? N4 Ni1 N2 C6 17.1(7) . . . . ? N2 Ni1 N3 C12 -164.39(17) . . . . ? N1 Ni1 N3 C12 -116.7(5) . . . . ? N4 Ni1 N3 C12 19.48(16) . . . . ? N2 Ni1 N3 C11 -11.74(16) . . . . ? N1 Ni1 N3 C11 36.0(6) . . . . ? N4 Ni1 N3 C11 172.13(16) . . . . ? N3 Ni1 N4 C16 -132.06(18) . . . . ? N2 Ni1 N4 C16 -162.4(6) . . . . ? N1 Ni1 N4 C16 41.18(18) . . . . ? N3 Ni1 N4 C13 -10.06(14) . . . . ? N2 Ni1 N4 C13 -40.4(7) . . . . ? N1 Ni1 N4 C13 163.17(14) . . . . ? C4 N1 C1 C2 23.7(2) . . . . ? Ni1 N1 C1 C2 149.24(17) . . . . ? N1 C1 C2 C3 -38.5(3) . . . . ? C1 C2 C3 C4 37.8(3) . . . . ? C1 N1 C4 C5 126.2(2) . . . . ? Ni1 N1 C4 C5 -5.7(2) . . . . ? C1 N1 C4 C3 0.3(2) . . . . ? Ni1 N1 C4 C3 -131.68(17) . . . . ? C2 C3 C4 N1 -24.0(3) . . . . ? C2 C3 C4 C5 -146.8(2) . . . . ? C6 N2 C5 O1 5.5(4) . . . . ? Ni1 N2 C5 O1 165.7(2) . . . . ? C6 N2 C5 C4 -177.31(19) . . . . ? Ni1 N2 C5 C4 -17.1(3) . . . . ? N1 C4 C5 O1 -168.3(2) . . . . ? C3 C4 C5 O1 -47.5(3) . . . . ? N1 C4 C5 N2 14.2(3) . . . . ? C3 C4 C5 N2 135.0(2) . . . . ? C5 N2 C6 C7 -42.6(3) . . . . ? Ni1 N2 C6 C7 156.31(17) . . . . ? C5 N2 C6 C11 -165.9(2) . . . . ? Ni1 N2 C6 C11 33.0(2) . . . . ? N2 C6 C7 C8 -179.12(19) . . . . ? C11 C6 C7 C8 -58.1(3) . . . . ? C6 C7 C8 C9 54.4(3) . . . . ? C7 C8 C9 C10 -53.8(3) . . . . ? C8 C9 C10 C11 56.0(3) . . . . ? C12 N3 C11 C10 -53.8(3) . . . . ? Ni1 N3 C11 C10 155.67(18) . . . . ? C12 N3 C11 C6 -177.2(2) . . . . ? Ni1 N3 C11 C6 32.2(2) . . . . ? C9 C10 C11 N3 177.3(2) . . . . ? C9 C10 C11 C6 -61.0(3) . . . . ? N2 C6 C11 N3 -39.8(2) . . . . ? C7 C6 C11 N3 -168.56(18) . . . . ? N2 C6 C11 C10 -168.07(18) . . . . ? C7 C6 C11 C10 63.2(3) . . . . ? C11 N3 C12 O2 6.7(4) . . . . ? Ni1 N3 C12 O2 156.36(19) . . . . ? C11 N3 C12 C13 -172.64(19) . . . . ? Ni1 N3 C12 C13 -22.9(2) . . . . ? C16 N4 C13 C14 6.9(2) . . . . ? Ni1 N4 C13 C14 -122.79(19) . . . . ? C16 N4 C13 C12 130.7(2) . . . . ? Ni1 N4 C13 C12 1.0(2) . . . . ? O2 C12 C13 N4 -166.01(19) . . . . ? N3 C12 C13 N4 13.3(3) . . . . ? O2 C12 C13 C14 -47.1(3) . . . . ? N3 C12 C13 C14 132.3(2) . . . . ? N4 C13 C14 C15 -28.8(3) . . . . ? C12 C13 C14 C15 -150.4(2) . . . . ? C13 C14 C15 C16 39.8(3) . . . . ? C14 C15 C16 N4 -35.9(3) . . . . ? C13 N4 C16 C15 17.7(3) . . . . ? Ni1 N4 C16 C15 141.18(19) . . . . ? 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 O3 H3OA O5 0.85(4) 2.00(5) 2.844(4) 171(5) 2_665 O3 H3OB O1 0.79(4) 2.08(4) 2.864(3) 170(3) . O4 H4OA O2 0.93(4) 1.93(4) 2.827(3) 162(3) . O4 H4OB O1 0.78(4) 2.00(4) 2.786(3) 177(4) 1_565 O5 H5OA O3 0.894(18) 1.96(2) 2.848(4) 171(3) 3 O5 H5OB O4 0.850(19) 2.10(3) 2.895(3) 155(4) 3_565 N1 H1N O2 0.91 2.10 2.982(2) 162.7 3_465 N4 H4N O4 0.91 2.10 3.008(3) 171.8 3_565 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.523 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.048 #===END data_rrf5 _database_code_CSD 169591 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H26 N4 Ni O4' _chemical_formula_weight 409.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.760(2) _cell_length_b 18.409(3) _cell_length_c 8.571(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1855.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 47.60 _cell_measurement_theta_max 50.30 _exptl_crystal_description columnar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.063 _exptl_crystal_size_min 0.063 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.770 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.689 _exptl_absorpt_correction_T_max 0.843 _exptl_absorpt_process_details ; analytical (de Meulenaer & Tompa, 1965) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.98 _diffrn_reflns_number 1931 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.46 _diffrn_reflns_theta_max 67.60 _reflns_number_total 1931 _reflns_number_gt 1808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR97 (Altomare, et. al. 1998) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XSHELL _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0669P)^2^+0.6801P] 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 0.00024(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(5) _refine_ls_number_reflns 1931 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.003 _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 0.23586(4) 0.12035(3) 0.60833(6) 0.03236(18) Uani 1 1 d . . . O1 O 0.1617(2) -0.07253(14) 0.4394(3) 0.0510(7) Uani 1 1 d . . . O2 O 0.0320(2) 0.23312(16) 0.8814(4) 0.0576(7) Uani 1 1 d . . . O3 O 0.0465(3) 0.2953(2) 0.1682(4) 0.0817(12) Uani 1 1 d . . . H3O H 0.0293 0.2735 0.0882 0.123 Uiso 1 1 calc R . . O4 O 0.3827(4) 0.1561(2) 0.2070(4) 0.0751(10) Uani 1 1 d . . . N1 N 0.3607(3) 0.07709(16) 0.4981(3) 0.0382(6) Uani 1 1 d . . . H1N H 0.3703 0.1024 0.4078 0.046 Uiso 1 1 calc R . . N2 N 0.1491(2) 0.04465(16) 0.5366(3) 0.0359(6) Uani 1 1 d . . . N3 N 0.1040(2) 0.15271(15) 0.7012(3) 0.0372(6) Uani 1 1 d . . . N4 N 0.3089(3) 0.20299(15) 0.7017(3) 0.0388(6) Uani 1 1 d . . . H4N H 0.3735 0.1874 0.7496 0.047 Uiso 1 1 calc R . . C1 C 0.4749(3) 0.0729(2) 0.5777(6) 0.0553(11) Uani 1 1 d . . . H1A H 0.5290 0.1045 0.5258 0.066 Uiso 1 1 calc R . . H1B H 0.4683 0.0881 0.6857 0.066 Uiso 1 1 calc R . . C2 C 0.5136(4) -0.0039(3) 0.5691(7) 0.0646(13) Uani 1 1 d . . . H2A H 0.5571 -0.0171 0.6610 0.078 Uiso 1 1 calc R . . H2B H 0.5597 -0.0121 0.4770 0.078 Uiso 1 1 calc R . . C3 C 0.4019(3) -0.0467(2) 0.5607(5) 0.0508(9) Uani 1 1 d . . . H3A H 0.4138 -0.0946 0.5163 0.061 Uiso 1 1 calc R . . H3B H 0.3676 -0.0517 0.6631 0.061 Uiso 1 1 calc R . . C4 C 0.3293(3) 0.00003(18) 0.4549(4) 0.0379(8) Uani 1 1 d . . . H4 H 0.3501 -0.0091 0.3459 0.045 Uiso 1 1 calc R . . C5 C 0.2020(3) -0.01251(19) 0.4762(4) 0.0367(7) Uani 1 1 d . . . C6 C 0.0328(3) 0.04799(19) 0.5785(4) 0.0370(7) Uani 1 1 d . . . C7 C -0.0524(3) -0.0017(2) 0.5407(5) 0.0477(9) Uani 1 1 d . . . H7 H -0.0360 -0.0422 0.4800 0.057 Uiso 1 1 calc R . . C8 C -0.1622(3) 0.0102(2) 0.5950(6) 0.0563(10) Uani 1 1 d . . . H8 H -0.2197 -0.0225 0.5699 0.068 Uiso 1 1 calc R . . C9 C -0.1866(3) 0.0701(2) 0.6859(6) 0.0560(10) Uani 1 1 d . . . H9 H -0.2605 0.0773 0.7216 0.067 Uiso 1 1 calc R . . C10 C -0.1026(3) 0.1199(2) 0.7248(5) 0.0495(9) Uani 1 1 d . . . H10 H -0.1198 0.1601 0.7861 0.059 Uiso 1 1 calc R . . C11 C 0.0075(3) 0.10897(18) 0.6710(4) 0.0383(7) Uani 1 1 d . . . C12 C 0.1114(3) 0.20654(18) 0.8029(4) 0.0403(8) Uani 1 1 d . . . C13 C 0.2315(4) 0.23388(18) 0.8237(4) 0.0458(8) Uani 1 1 d . . . H13 H 0.2588 0.2180 0.9263 0.055 Uiso 1 1 calc R . . C14 C 0.2415(5) 0.3172(2) 0.8152(8) 0.0784(16) Uani 1 1 d . . . H14A H 0.1706 0.3388 0.7808 0.094 Uiso 1 1 calc R . . H14B H 0.2615 0.3373 0.9162 0.094 Uiso 1 1 calc R . . C15 C 0.3345(7) 0.3306(3) 0.6984(8) 0.105(2) Uani 1 1 d . . . H15A H 0.3177 0.3734 0.6364 0.126 Uiso 1 1 calc R . . H15B H 0.4067 0.3379 0.7509 0.126 Uiso 1 1 calc R . . C16 C 0.3391(5) 0.2646(2) 0.5974(5) 0.0654(12) Uani 1 1 d . . . H16A H 0.2852 0.2684 0.5121 0.079 Uiso 1 1 calc R . . H16B H 0.4147 0.2581 0.5544 0.079 Uiso 1 1 calc R . . C17 C 0.1283(5) 0.2567(4) 0.2474(8) 0.100(2) Uani 1 1 d . . . H17A H 0.1987 0.2588 0.1910 0.149 Uiso 1 1 calc R . . H17B H 0.1046 0.2070 0.2574 0.149 Uiso 1 1 calc R . . H17C H 0.1387 0.2774 0.3493 0.149 Uiso 1 1 calc R . . H4OA H 0.373(6) 0.126(3) 0.137(7) 0.10(2) Uiso 1 1 d . . . H4OB H 0.444(5) 0.194(3) 0.183(8) 0.10(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 0.0378(3) 0.0306(3) 0.0287(3) -0.0023(2) 0.0010(2) -0.0026(2) O1 0.0526(15) 0.0408(13) 0.0595(16) -0.0163(13) 0.0023(13) -0.0092(12) O2 0.0584(15) 0.0560(15) 0.0585(17) -0.0174(15) -0.0012(16) 0.0192(13) O3 0.071(2) 0.108(3) 0.066(2) -0.036(2) 0.0005(18) 0.024(2) O4 0.099(3) 0.069(2) 0.057(2) 0.0037(18) 0.015(2) -0.032(2) N1 0.0437(15) 0.0398(15) 0.0311(14) -0.0053(12) 0.0041(13) -0.0055(13) N2 0.0374(14) 0.0367(14) 0.0335(14) -0.0004(12) -0.0005(12) -0.0033(12) N3 0.0407(15) 0.0341(13) 0.0367(15) -0.0024(13) -0.0013(13) 0.0024(13) N4 0.0472(16) 0.0333(12) 0.0359(14) -0.0015(13) -0.0039(13) -0.0052(13) C1 0.0403(18) 0.058(2) 0.068(3) -0.014(2) 0.000(2) -0.0070(18) C2 0.048(2) 0.073(3) 0.073(3) -0.018(3) -0.006(2) 0.008(2) C3 0.053(2) 0.0434(19) 0.055(2) -0.0066(18) 0.0001(19) 0.0059(18) C4 0.0422(18) 0.0396(18) 0.0319(15) -0.0095(15) 0.0053(14) -0.0052(15) C5 0.0466(19) 0.0355(16) 0.0280(15) -0.0050(14) -0.0001(14) -0.0035(14) C6 0.0373(16) 0.0393(17) 0.0344(18) 0.0047(14) -0.0043(14) -0.0026(14) C7 0.0434(19) 0.045(2) 0.054(2) 0.0050(19) -0.0068(18) -0.0026(16) C8 0.0374(17) 0.056(2) 0.076(3) 0.008(2) -0.009(2) -0.0070(16) C9 0.0334(17) 0.068(2) 0.067(2) 0.014(2) 0.0013(19) 0.0021(19) C10 0.0443(19) 0.053(2) 0.052(2) 0.003(2) 0.0028(17) 0.0095(19) C11 0.0380(16) 0.0411(17) 0.0357(16) 0.0094(15) -0.0021(14) 0.0047(15) C12 0.053(2) 0.0325(15) 0.0359(18) 0.0001(15) -0.0039(16) 0.0125(16) C13 0.062(2) 0.0340(16) 0.0413(17) -0.0081(14) -0.0030(19) 0.0048(17) C14 0.091(4) 0.0334(19) 0.111(4) -0.012(2) 0.009(4) -0.009(2) C15 0.182(7) 0.040(2) 0.093(4) 0.003(3) 0.023(5) -0.017(3) C16 0.099(3) 0.051(2) 0.047(2) 0.006(2) 0.002(3) -0.032(2) C17 0.067(3) 0.138(6) 0.094(4) -0.041(4) -0.017(3) 0.026(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 N2 1.833(3) . ? Ni1 N3 1.842(3) . ? Ni1 N1 1.919(3) . ? Ni1 N4 1.922(3) . ? O1 C5 1.243(4) . ? O2 C12 1.250(5) . ? O3 C17 1.375(7) . ? O3 H3O 0.8200 . ? O4 H4OA 0.82(6) . ? O4 H4OB 1.02(6) . ? N1 C1 1.509(5) . ? N1 C4 1.512(4) . ? N1 H1N 0.9100 . ? N2 C5 1.327(5) . ? N2 C6 1.416(4) . ? N3 C12 1.323(4) . ? N3 C11 1.415(5) . ? N4 C16 1.487(5) . ? N4 C13 1.499(5) . ? N4 H4N 0.9100 . ? C1 C2 1.486(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.534(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.514(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.526(5) . ? C4 H4 0.9800 . ? C6 C7 1.396(5) . ? C6 C11 1.406(5) . ? C7 C8 1.389(6) . ? C7 H7 0.9300 . ? C8 C9 1.381(6) . ? C8 H8 0.9300 . ? C9 C10 1.389(6) . ? C9 H9 0.9300 . ? C10 C11 1.389(5) . ? C10 H10 0.9300 . ? C12 C13 1.510(5) . ? C13 C14 1.541(5) . ? C13 H13 0.9800 . ? C14 C15 1.503(9) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.494(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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 85.55(12) . . ? N2 Ni1 N1 86.84(12) . . ? N3 Ni1 N1 172.31(13) . . ? N2 Ni1 N4 172.00(13) . . ? N3 Ni1 N4 86.59(13) . . ? N1 Ni1 N4 101.05(13) . . ? C17 O3 H3O 109.5 . . ? H4OA O4 H4OB 114(6) . . ? C1 N1 C4 106.3(3) . . ? C1 N1 Ni1 118.6(2) . . ? C4 N1 Ni1 108.9(2) . . ? C1 N1 H1N 107.5 . . ? C4 N1 H1N 107.5 . . ? Ni1 N1 H1N 107.5 . . ? C5 N2 C6 125.9(3) . . ? C5 N2 Ni1 118.2(2) . . ? C6 N2 Ni1 114.8(2) . . ? C12 N3 C11 126.8(3) . . ? C12 N3 Ni1 118.1(3) . . ? C11 N3 Ni1 114.3(2) . . ? C16 N4 C13 106.0(3) . . ? C16 N4 Ni1 117.3(2) . . ? C13 N4 Ni1 108.6(2) . . ? C16 N4 H4N 108.2 . . ? C13 N4 H4N 108.2 . . ? Ni1 N4 H4N 108.2 . . ? C2 C1 N1 107.4(3) . . ? C2 C1 H1A 110.2 . . ? N1 C1 H1A 110.2 . . ? C2 C1 H1B 110.2 . . ? N1 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? C1 C2 C3 103.2(3) . . ? C1 C2 H2A 111.1 . . ? C3 C2 H2A 111.1 . . ? C1 C2 H2B 111.1 . . ? C3 C2 H2B 111.1 . . ? H2A C2 H2B 109.1 . . ? C4 C3 C2 102.6(3) . . ? C4 C3 H3A 111.2 . . ? C2 C3 H3A 111.2 . . ? C4 C3 H3B 111.2 . . ? C2 C3 H3B 111.2 . . ? H3A C3 H3B 109.2 . . ? N1 C4 C3 104.4(3) . . ? N1 C4 C5 110.6(3) . . ? C3 C4 C5 113.3(3) . . ? N1 C4 H4 109.5 . . ? C3 C4 H4 109.5 . . ? C5 C4 H4 109.5 . . ? O1 C5 N2 128.7(3) . . ? O1 C5 C4 118.6(3) . . ? N2 C5 C4 112.7(3) . . ? C7 C6 C11 120.1(3) . . ? C7 C6 N2 127.4(3) . . ? C11 C6 N2 112.5(3) . . ? C8 C7 C6 119.1(4) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C9 C8 C7 120.5(4) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 121.0(4) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C11 119.2(4) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C10 C11 C6 120.0(3) . . ? C10 C11 N3 127.1(3) . . ? C6 C11 N3 112.8(3) . . ? O2 C12 N3 126.8(4) . . ? O2 C12 C13 120.3(3) . . ? N3 C12 C13 112.9(3) . . ? N4 C13 C12 111.1(3) . . ? N4 C13 C14 107.4(4) . . ? C12 C13 C14 113.5(4) . . ? N4 C13 H13 108.3 . . ? C12 C13 H13 108.3 . . ? C14 C13 H13 108.3 . . ? C15 C14 C13 104.5(4) . . ? C15 C14 H14A 110.8 . . ? C13 C14 H14A 110.8 . . ? C15 C14 H14B 110.8 . . ? C13 C14 H14B 110.8 . . ? H14A C14 H14B 108.9 . . ? C16 C15 C14 106.2(4) . . ? C16 C15 H15A 110.5 . . ? C14 C15 H15A 110.5 . . ? C16 C15 H15B 110.5 . . ? C14 C15 H15B 110.5 . . ? H15A C15 H15B 108.7 . . ? N4 C16 C15 105.3(4) . . ? N4 C16 H16A 110.7 . . ? C15 C16 H16A 110.7 . . ? N4 C16 H16B 110.7 . . ? C15 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 C1 -136.4(3) . . . . ? N3 Ni1 N1 C1 -144.4(9) . . . . ? N4 Ni1 N1 C1 42.2(3) . . . . ? N2 Ni1 N1 C4 -14.8(2) . . . . ? N3 Ni1 N1 C4 -22.8(11) . . . . ? N4 Ni1 N1 C4 163.8(2) . . . . ? N3 Ni1 N2 C5 -167.0(3) . . . . ? N1 Ni1 N2 C5 14.1(3) . . . . ? N4 Ni1 N2 C5 -156.2(8) . . . . ? N3 Ni1 N2 C6 1.7(2) . . . . ? N1 Ni1 N2 C6 -177.2(2) . . . . ? N4 Ni1 N2 C6 12.5(11) . . . . ? N2 Ni1 N3 C12 169.3(3) . . . . ? N1 Ni1 N3 C12 177.3(9) . . . . ? N4 Ni1 N3 C12 -9.2(3) . . . . ? N2 Ni1 N3 C11 -1.8(2) . . . . ? N1 Ni1 N3 C11 6.2(11) . . . . ? N4 Ni1 N3 C11 179.7(2) . . . . ? N2 Ni1 N4 C16 -116.6(9) . . . . ? N3 Ni1 N4 C16 -105.8(3) . . . . ? N1 Ni1 N4 C16 73.3(3) . . . . ? N2 Ni1 N4 C13 3.5(10) . . . . ? N3 Ni1 N4 C13 14.3(2) . . . . ? N1 Ni1 N4 C13 -166.6(2) . . . . ? C4 N1 C1 C2 4.6(5) . . . . ? Ni1 N1 C1 C2 127.5(4) . . . . ? N1 C1 C2 C3 -27.3(5) . . . . ? C1 C2 C3 C4 39.5(5) . . . . ? C1 N1 C4 C3 20.3(4) . . . . ? Ni1 N1 C4 C3 -108.5(3) . . . . ? C1 N1 C4 C5 142.5(3) . . . . ? Ni1 N1 C4 C5 13.6(3) . . . . ? C2 C3 C4 N1 -36.7(4) . . . . ? C2 C3 C4 C5 -157.1(3) . . . . ? C6 N2 C5 O1 2.8(6) . . . . ? Ni1 N2 C5 O1 170.1(3) . . . . ? C6 N2 C5 C4 -175.9(3) . . . . ? Ni1 N2 C5 C4 -8.7(4) . . . . ? N1 C4 C5 O1 177.1(3) . . . . ? C3 C4 C5 O1 -66.0(4) . . . . ? N1 C4 C5 N2 -4.0(4) . . . . ? C3 C4 C5 N2 112.8(3) . . . . ? C5 N2 C6 C7 -12.3(6) . . . . ? Ni1 N2 C6 C7 -180.0(3) . . . . ? C5 N2 C6 C11 166.4(3) . . . . ? Ni1 N2 C6 C11 -1.2(4) . . . . ? C11 C6 C7 C8 0.3(6) . . . . ? N2 C6 C7 C8 178.9(4) . . . . ? C6 C7 C8 C9 -0.3(6) . . . . ? C7 C8 C9 C10 0.2(7) . . . . ? C8 C9 C10 C11 0.0(6) . . . . ? C9 C10 C11 C6 -0.1(6) . . . . ? C9 C10 C11 N3 -178.6(3) . . . . ? C7 C6 C11 C10 -0.1(5) . . . . ? N2 C6 C11 C10 -178.9(3) . . . . ? C7 C6 C11 N3 178.6(3) . . . . ? N2 C6 C11 N3 -0.2(4) . . . . ? C12 N3 C11 C10 9.9(6) . . . . ? Ni1 N3 C11 C10 -179.9(3) . . . . ? C12 N3 C11 C6 -168.6(3) . . . . ? Ni1 N3 C11 C6 1.6(4) . . . . ? C11 N3 C12 O2 -6.9(6) . . . . ? Ni1 N3 C12 O2 -176.7(3) . . . . ? C11 N3 C12 C13 170.8(3) . . . . ? Ni1 N3 C12 C13 1.0(4) . . . . ? C16 N4 C13 C12 110.0(4) . . . . ? Ni1 N4 C13 C12 -16.9(3) . . . . ? C16 N4 C13 C14 -14.6(5) . . . . ? Ni1 N4 C13 C14 -141.5(3) . . . . ? O2 C12 C13 N4 -171.2(3) . . . . ? N3 C12 C13 N4 10.9(4) . . . . ? O2 C12 C13 C14 -50.1(6) . . . . ? N3 C12 C13 C14 132.0(4) . . . . ? N4 C13 C14 C15 -5.7(6) . . . . ? C12 C13 C14 C15 -128.8(5) . . . . ? C13 C14 C15 C16 23.8(7) . . . . ? C13 N4 C16 C15 29.4(6) . . . . ? Ni1 N4 C16 C15 150.9(4) . . . . ? C14 C15 C16 N4 -33.5(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 O3 H3O O2 0.82 1.92 2.717(5) 162.9 1_554 O4 H4OA O1 0.82(6) 2.00(6) 2.810(5) 167(6) 2_554 O4 H4OB O2 1.02(6) 1.79(7) 2.797(4) 170(5) 3_556 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 67.60 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.434 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.052 #===END data_rrf8 _database_code_CSD 169592 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N4 Ni O3' _chemical_formula_weight 327.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 32 2 1 ' _symmetry_Int_Tables_number 154 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'y, x, -z' '-x, -x+y, -z+2/3' 'x-y, -y, -z+1/3' _cell_length_a 8.5856(14) _cell_length_b 8.5856 _cell_length_c 17.3694(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1108.8(2) _cell_formula_units_Z 3 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.7 _cell_measurement_theta_max 15.45 _exptl_crystal_description 'cut prism' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 510 _exptl_absorpt_coefficient_mu 2.017 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; \y scans (North,Phillips & Matthews, 1968) ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% -1.27 _diffrn_reflns_number 1514 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.95 _diffrn_reflns_theta_max 67.65 _reflns_number_total 1335 _reflns_number_gt 1266 _reflns_threshold_expression >2sigma(I) _reflns_special_details ; The reflns_number_total includes Friedels, the number of unique reflections is 824 (according to texsan) ; _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows (MSC, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'teXsan for Windows (MSC, 1997)' _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^)+(0.0712P)^2^+0.5074P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(5) _refine_ls_number_reflns 1335 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.37417(7) 0.37417(7) 0.5000 0.0301(2) Uani 1 2 d S . . O1 O 0.0194(4) 0.3051(4) 0.65810(14) 0.0532(7) Uani 1 1 d . . . O2 O 0.6771(5) 1.0000 0.6667 0.0601(9) Uani 1 2 d S . . N1 N 0.4429(3) 0.5890(3) 0.55880(13) 0.0327(6) Uani 1 1 d . . . H1N H 0.5448 0.6171 0.5856 0.039 Uiso 1 1 calc R . . N2 N 0.1633(3) 0.2745(4) 0.55337(14) 0.0397(6) Uani 1 1 d . . . C1 C 0.4774(5) 0.7478(5) 0.51056(19) 0.0466(8) Uani 1 1 d . . . H1A H 0.5708 0.8589 0.5331 0.056 Uiso 1 1 calc R . . H1B H 0.5128 0.7367 0.4587 0.056 Uiso 1 1 calc R . . C2 C 0.3017(7) 0.7423(7) 0.5105(3) 0.0745(13) Uani 1 1 d . . . H2A H 0.2185 0.6525 0.4747 0.089 Uiso 1 1 calc R . . H2B H 0.3165 0.8585 0.4969 0.089 Uiso 1 1 calc R . . C3 C 0.2366(6) 0.6926(6) 0.5927(3) 0.0654(12) Uani 1 1 d . . . H3A H 0.1068 0.6378 0.5956 0.079 Uiso 1 1 calc R . . H3B H 0.2915 0.7974 0.6259 0.079 Uiso 1 1 calc R . . C4 C 0.2970(5) 0.5570(5) 0.61516(18) 0.0364(7) Uani 1 1 d . . . H4 H 0.3465 0.5829 0.6675 0.044 Uiso 1 1 calc R . . C5 C 0.1454(4) 0.3645(4) 0.61060(16) 0.0355(7) Uani 1 1 d . . . C6 C 0.0407(5) 0.0828(5) 0.5401(2) 0.0510(9) Uani 1 1 d . . . H6A H -0.0832 0.0556 0.5429 0.061 Uiso 1 1 calc R . . H6B H 0.0591 0.0117 0.5786 0.061 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 0.0315(3) 0.0315(3) 0.0234(3) -0.00312(13) 0.00312(13) 0.0128(3) O1 0.0545(14) 0.0455(14) 0.0477(13) -0.0086(11) 0.0232(12) 0.0161(11) O2 0.0601(16) 0.058(2) 0.062(2) -0.0072(16) -0.0036(8) 0.0289(11) N1 0.0366(14) 0.0317(12) 0.0239(11) -0.0040(9) -0.0026(9) 0.0126(11) N2 0.0336(12) 0.0400(14) 0.0367(13) -0.0082(12) 0.0110(10) 0.0117(12) C1 0.060(2) 0.0385(17) 0.0380(16) 0.0030(14) 0.0004(15) 0.0225(16) C2 0.073(3) 0.063(3) 0.093(3) 0.018(3) -0.014(3) 0.037(2) C3 0.057(2) 0.041(2) 0.101(3) -0.006(2) 0.010(2) 0.0270(19) C4 0.0378(16) 0.0415(16) 0.0278(13) -0.0082(12) -0.0004(12) 0.0183(14) C5 0.0369(15) 0.0391(16) 0.0297(14) -0.0041(12) 0.0027(12) 0.0182(13) C6 0.0477(19) 0.0390(17) 0.053(2) -0.0135(15) 0.0210(17) 0.0114(15) _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 1.822(2) 4_556 ? Ni1 N2 1.822(2) . ? Ni1 N1 1.925(2) . ? Ni1 N1 1.925(2) 4_556 ? O1 C5 1.249(4) . ? N1 C1 1.498(4) . ? N1 C4 1.503(4) . ? N1 H1N 0.9100 . ? N2 C5 1.314(4) . ? N2 C6 1.462(4) . ? C1 C2 1.485(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.514(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.542(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.510(5) . ? C4 H4 0.9800 . ? C6 C6 1.528(6) 4_556 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? 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 N2 85.97(17) 4_556 . ? N2 Ni1 N1 171.40(13) 4_556 . ? N2 Ni1 N1 86.36(11) . . ? N2 Ni1 N1 86.36(11) 4_556 4_556 ? N2 Ni1 N1 171.40(13) . 4_556 ? N1 Ni1 N1 101.54(15) . 4_556 ? C1 N1 C4 107.3(3) . . ? C1 N1 Ni1 113.69(18) . . ? C4 N1 Ni1 110.01(19) . . ? C1 N1 H1N 108.6 . . ? C4 N1 H1N 108.6 . . ? Ni1 N1 H1N 108.6 . . ? C5 N2 C6 123.4(2) . . ? C5 N2 Ni1 119.3(2) . . ? C6 N2 Ni1 115.8(2) . . ? C2 C1 N1 103.6(3) . . ? C2 C1 H1A 111.0 . . ? N1 C1 H1A 111.0 . . ? C2 C1 H1B 111.0 . . ? N1 C1 H1B 111.0 . . ? H1A C1 H1B 109.0 . . ? C1 C2 C3 103.6(4) . . ? C1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? C1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? C2 C3 C4 103.6(3) . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3A 111.0 . . ? C2 C3 H3B 111.0 . . ? C4 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? N1 C4 C5 110.5(2) . . ? N1 C4 C3 105.1(3) . . ? C5 C4 C3 112.4(3) . . ? N1 C4 H4 109.6 . . ? C5 C4 H4 109.6 . . ? C3 C4 H4 109.6 . . ? O1 C5 N2 126.3(3) . . ? O1 C5 C4 120.6(3) . . ? N2 C5 C4 113.1(3) . . ? N2 C6 C6 106.7(2) . 4_556 ? N2 C6 H6A 110.4 . . ? C6 C6 H6A 110.4 4_556 . ? N2 C6 H6B 110.4 . . ? C6 C6 H6B 110.4 4_556 . ? H6A C6 H6B 108.6 . . ? 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 N2 Ni1 N1 C1 -91.5(8) 4_556 . . . ? N2 Ni1 N1 C1 -118.4(2) . . . . ? N1 Ni1 N1 C1 65.0(2) 4_556 . . . ? N2 Ni1 N1 C4 29.0(8) 4_556 . . . ? N2 Ni1 N1 C4 2.0(2) . . . . ? N1 Ni1 N1 C4 -174.6(2) 4_556 . . . ? N2 Ni1 N2 C5 176.8(4) 4_556 . . . ? N1 Ni1 N2 C5 -7.1(3) . . . . ? N1 Ni1 N2 C5 149.8(7) 4_556 . . . ? N2 Ni1 N2 C6 10.1(2) 4_556 . . . ? N1 Ni1 N2 C6 -173.8(3) . . . . ? N1 Ni1 N2 C6 -16.9(10) 4_556 . . . ? C4 N1 C1 C2 -28.4(4) . . . . ? Ni1 N1 C1 C2 93.5(3) . . . . ? N1 C1 C2 C3 40.7(4) . . . . ? C1 C2 C3 C4 -37.4(5) . . . . ? C1 N1 C4 C5 126.5(3) . . . . ? Ni1 N1 C4 C5 2.4(3) . . . . ? C1 N1 C4 C3 5.0(3) . . . . ? Ni1 N1 C4 C3 -119.1(3) . . . . ? C2 C3 C4 N1 19.7(4) . . . . ? C2 C3 C4 C5 -100.5(4) . . . . ? C6 N2 C5 O1 -4.5(6) . . . . ? Ni1 N2 C5 O1 -170.2(3) . . . . ? C6 N2 C5 C4 175.6(3) . . . . ? Ni1 N2 C5 C4 9.9(4) . . . . ? N1 C4 C5 O1 172.6(3) . . . . ? C3 C4 C5 O1 -70.3(4) . . . . ? N1 C4 C5 N2 -7.5(4) . . . . ? C3 C4 C5 N2 109.6(4) . . . . ? C5 N2 C6 C6 167.9(4) . . . 4_556 ? Ni1 N2 C6 C6 -26.0(5) . . . 4_556 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 67.65 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.471 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.062