# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Ju Chang Kim' 'Jaeheung Cho' 'Hyojin Kim' 'Alan J. Lough' _publ_contact_author_name 'Prof Ju Chang Kim' _publ_contact_author_address ; Department of Chemistry Pukyong National University Pusan 608-737 KOREA ; _publ_contact_author_email KIMJC@PKNU.AC.KR _publ_requested_journal 'Chemical Communications' _publ_section_title ; Isolation and characterization of the first stable bicarbonato complex in a nickel (II) system: Identification of unusual monodentate coordination ; data_k0442 _database_code_depnum_ccdc_archive 'CCDC 236194' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H42 N4 Ni O6' _chemical_formula_sum 'C22 H42 N4 Ni O6' _chemical_formula_weight 517.31 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4397(3) _cell_length_b 9.2719(3) _cell_length_c 10.3211(4) _cell_angle_alpha 106.5530(18) _cell_angle_beta 101.265(2) _cell_angle_gamma 109.4730(18) _cell_volume 609.30(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 12839 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 278 _exptl_absorpt_coefficient_mu 0.841 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.817 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _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' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7277 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2771 _reflns_number_gt 2557 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXTL V6.12(Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL V6.12' _computing_publication_material 'SHELXTL V6.12' _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^)+(0.0284P)^2^+0.2709P] 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 ? _refine_ls_extinction_coef none _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2771 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.5000 0.5000 0.5000 0.01743(11) Uani 1 2 d S . . O1 O 0.19899(16) 0.32876(14) 0.44044(12) 0.0244(3) Uani 1 1 d . . . O2 O 0.17780(19) 0.18190(15) 0.57981(13) 0.0345(3) Uani 1 1 d . . . O3 O -0.01783(19) 0.06938(15) 0.35161(12) 0.0272(3) Uani 1 1 d . . . N1 N 0.41476(19) 0.57903(16) 0.33605(14) 0.0195(3) Uani 1 1 d . . . H1 H 0.5298 0.6710 0.3520 0.023 Uiso 1 1 calc R . . N2 N 0.5391(2) 0.32881(16) 0.34102(14) 0.0207(3) Uani 1 1 d . . . H2 H 0.4211 0.2325 0.3026 0.025 Uiso 1 1 calc R . . C1 C 0.2579(2) 0.6442(2) 0.33816(17) 0.0245(3) Uani 1 1 d . . . H1A H 0.1270 0.5514 0.3197 0.029 Uiso 1 1 calc R . . C2 C 0.3157(3) 0.7757(2) 0.48705(18) 0.0266(4) Uani 1 1 d . . . H2A H 0.4576 0.8539 0.5134 0.032 Uiso 1 1 calc R . . H2B H 0.2321 0.8387 0.4806 0.032 Uiso 1 1 calc R . . C3 C 0.2939(3) 0.7148(2) 0.60765(18) 0.0269(4) Uani 1 1 d . . . H3A H 0.2907 0.8021 0.6879 0.032 Uiso 1 1 calc R . . H3B H 0.1646 0.6166 0.5739 0.032 Uiso 1 1 calc R . . C4 C 0.2304(3) 0.7197(3) 0.2259(2) 0.0370(4) Uani 1 1 d . . . H4A H 0.1863 0.6344 0.1304 0.056 Uiso 1 1 calc R . . H4B H 0.3586 0.8090 0.2412 0.056 Uiso 1 1 calc R . . H4C H 0.1287 0.7640 0.2341 0.056 Uiso 1 1 calc R . . C5 C 0.3934(3) 0.4573(2) 0.19760(17) 0.0236(3) Uani 1 1 d . . . H5A H 0.4219 0.5181 0.1328 0.028 Uiso 1 1 calc R . . C6 C 0.1849(3) 0.3147(2) 0.12175(18) 0.0301(4) Uani 1 1 d . . . H6A H 0.0834 0.3587 0.0997 0.036 Uiso 1 1 calc R . . H6B H 0.1493 0.2549 0.1850 0.036 Uiso 1 1 calc R . . C7 C 0.1838(3) 0.1957(3) -0.0168(2) 0.0402(5) Uani 1 1 d . . . H7A H 0.0500 0.1012 -0.0626 0.048 Uiso 1 1 calc R . . H7B H 0.2063 0.2535 -0.0833 0.048 Uiso 1 1 calc R . . C8 C 0.3455(4) 0.1312(3) 0.0101(2) 0.0419(5) Uani 1 1 d . . . H8A H 0.3151 0.0631 0.0680 0.050 Uiso 1 1 calc R . . H8B H 0.3453 0.0603 -0.0821 0.050 Uiso 1 1 calc R . . C9 C 0.5527(3) 0.2737(2) 0.08809(19) 0.0349(4) Uani 1 1 d . . . H9A H 0.5897 0.3331 0.0248 0.042 Uiso 1 1 calc R . . H9B H 0.6533 0.2288 0.1101 0.042 Uiso 1 1 calc R . . C10 C 0.5595(3) 0.3960(2) 0.22725(17) 0.0240(3) Uani 1 1 d . . . H10A H 0.6923 0.4936 0.2650 0.029 Uiso 1 1 calc R . . C11 C 0.1263(2) 0.19841(19) 0.46302(17) 0.0214(3) Uani 1 1 d . . . H1O H -0.062(4) -0.006(3) 0.378(3) 0.052(7) 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 0.01851(16) 0.01527(16) 0.01805(16) 0.00871(11) 0.00420(11) 0.00538(11) O1 0.0200(5) 0.0205(6) 0.0309(6) 0.0161(5) 0.0043(5) 0.0030(5) O2 0.0325(7) 0.0266(6) 0.0288(7) 0.0177(5) -0.0027(5) -0.0052(5) O3 0.0323(6) 0.0186(6) 0.0227(6) 0.0092(5) 0.0044(5) 0.0026(5) N1 0.0207(6) 0.0180(6) 0.0197(6) 0.0092(5) 0.0050(5) 0.0068(5) N2 0.0229(7) 0.0194(6) 0.0201(6) 0.0097(5) 0.0048(5) 0.0086(5) C1 0.0257(8) 0.0281(9) 0.0251(8) 0.0146(7) 0.0070(7) 0.0143(7) C2 0.0330(9) 0.0276(9) 0.0283(9) 0.0150(7) 0.0111(7) 0.0188(7) C3 0.0336(9) 0.0324(9) 0.0248(8) 0.0143(7) 0.0116(7) 0.0211(8) C4 0.0504(12) 0.0493(12) 0.0316(10) 0.0246(9) 0.0152(9) 0.0353(10) C5 0.0299(8) 0.0237(8) 0.0187(8) 0.0106(6) 0.0069(7) 0.0113(7) C6 0.0315(9) 0.0288(9) 0.0221(8) 0.0081(7) -0.0012(7) 0.0101(7) C7 0.0527(12) 0.0325(10) 0.0229(9) 0.0040(8) -0.0024(8) 0.0165(9) C8 0.0656(14) 0.0348(11) 0.0214(9) 0.0045(8) 0.0048(9) 0.0265(10) C9 0.0546(12) 0.0402(11) 0.0237(9) 0.0157(8) 0.0166(8) 0.0306(10) C10 0.0307(8) 0.0253(8) 0.0207(8) 0.0121(7) 0.0094(7) 0.0136(7) C11 0.0181(7) 0.0203(8) 0.0256(8) 0.0105(6) 0.0071(6) 0.0061(6) _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 2.0753(13) . ? Ni1 N2 2.0753(13) 2_666 ? Ni1 N1 2.0975(13) 2_666 ? Ni1 N1 2.0975(13) . ? Ni1 O1 2.1093(11) 2_666 ? Ni1 O1 2.1093(11) . ? O1 C11 1.2576(19) . ? O2 C11 1.260(2) . ? O3 C11 1.335(2) . ? N1 C1 1.483(2) . ? N1 C5 1.488(2) . ? N2 C3 1.479(2) 2_666 ? N2 C10 1.488(2) . ? C1 C4 1.530(2) . ? C1 C2 1.536(2) . ? C2 C3 1.521(2) . ? C3 N2 1.479(2) 2_666 ? C5 C6 1.528(2) . ? C5 C10 1.537(2) . ? C6 C7 1.534(3) . ? C7 C8 1.525(3) . ? C8 C9 1.523(3) . ? C9 C10 1.535(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni1 N2 180.000(1) . 2_666 ? N2 Ni1 N1 96.49(5) . 2_666 ? N2 Ni1 N1 83.51(5) 2_666 2_666 ? N2 Ni1 N1 83.51(5) . . ? N2 Ni1 N1 96.49(5) 2_666 . ? N1 Ni1 N1 180.0 2_666 . ? N2 Ni1 O1 91.87(5) . 2_666 ? N2 Ni1 O1 88.13(5) 2_666 2_666 ? N1 Ni1 O1 89.29(5) 2_666 2_666 ? N1 Ni1 O1 90.71(5) . 2_666 ? N2 Ni1 O1 88.13(5) . . ? N2 Ni1 O1 91.87(5) 2_666 . ? N1 Ni1 O1 90.71(5) 2_666 . ? N1 Ni1 O1 89.29(5) . . ? O1 Ni1 O1 180.0 2_666 . ? C11 O1 Ni1 130.68(11) . . ? C1 N1 C5 117.14(12) . . ? C1 N1 Ni1 118.03(10) . . ? C5 N1 Ni1 109.02(9) . . ? C3 N2 C10 113.67(13) 2_666 . ? C3 N2 Ni1 114.03(10) 2_666 . ? C10 N2 Ni1 106.51(9) . . ? N1 C1 C4 112.86(14) . . ? N1 C1 C2 108.77(13) . . ? C4 C1 C2 109.32(14) . . ? C3 C2 C1 117.02(14) . . ? N2 C3 C2 111.97(13) 2_666 . ? N1 C5 C6 114.86(14) . . ? N1 C5 C10 106.89(12) . . ? C6 C5 C10 112.08(14) . . ? C5 C6 C7 109.91(16) . . ? C8 C7 C6 111.93(15) . . ? C9 C8 C7 110.83(16) . . ? C8 C9 C10 112.24(16) . . ? N2 C10 C9 114.50(14) . . ? N2 C10 C5 108.47(13) . . ? C9 C10 C5 110.24(14) . . ? O1 C11 O2 125.52(15) . . ? O1 C11 O3 115.43(14) . . ? O2 C11 O3 119.05(14) . . ? 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 N1 H1 O2 0.93 1.99 2.8724(18) 157.5 2_666 O3 H1O O2 0.81(3) 1.79(3) 2.6012(17) 175(3) 2_556 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.311 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.057 data_k0440 _database_code_depnum_ccdc_archive 'CCDC 236195' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H40 N4 Ni, 2(C H O3)' _chemical_formula_sum 'C22 H42 N4 Ni O6' _chemical_formula_weight 517.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3483(3) _cell_length_b 9.9583(3) _cell_length_c 12.8621(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.9710(16) _cell_angle_gamma 90.00 _cell_volume 1166.82(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 15100 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.878 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.730 _exptl_absorpt_correction_T_max 0.825 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _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' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8287 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2655 _reflns_number_gt 2365 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXTL V6.12(Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL V6.12' _computing_publication_material 'SHELXTL V6.12' _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^)+(0.0779P)^2^+1.4657P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2655 _refine_ls_number_parameters 156 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.069 _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 0.5000 0.5000 0.5000 0.01562(17) Uani 1 2 d S . . N1 N 0.46533(19) 0.57998(18) 0.35692(13) 0.0129(4) Uani 1 1 d . . . H1 H 0.3691 0.5574 0.3247 0.015 Uiso 1 1 calc R . . N2 N 0.56489(19) 0.34104(17) 0.43535(14) 0.0126(4) Uani 1 1 d . . . H2 H 0.6667 0.3448 0.4558 0.015 Uiso 1 1 calc R . . C1 C 0.4757(3) 0.7265(2) 0.33877(17) 0.0179(4) Uani 1 1 d . . . H1A H 0.4288 0.7470 0.2635 0.021 Uiso 1 1 calc R . . H1B H 0.5804 0.7522 0.3509 0.021 Uiso 1 1 calc R . . C2 C 0.4030(3) 0.8094(2) 0.41108(18) 0.0193(5) Uani 1 1 d . . . H2A H 0.2984 0.7832 0.3986 0.023 Uiso 1 1 calc R . . H2B H 0.4067 0.9052 0.3911 0.023 Uiso 1 1 calc R . . C3 C 0.4723(2) 0.7948(2) 0.52966(17) 0.0165(4) Uani 1 1 d . . . H3 H 0.4266 0.8631 0.5691 0.020 Uiso 1 1 calc R . . C4 C 0.6374(3) 0.8168(2) 0.55758(19) 0.0222(5) Uani 1 1 d . . . H4A H 0.6706 0.8306 0.6347 0.033 Uiso 1 1 calc R . . H4B H 0.6616 0.8960 0.5197 0.033 Uiso 1 1 calc R . . H4C H 0.6866 0.7378 0.5364 0.033 Uiso 1 1 calc R . . C5 C 0.5576(2) 0.50311(19) 0.29668(18) 0.0126(4) Uani 1 1 d . . . H5A H 0.6628 0.5244 0.3285 0.015 Uiso 1 1 calc R . . C6 C 0.5280(3) 0.5335(3) 0.17724(17) 0.0182(4) Uani 1 1 d . . . H6A H 0.4236 0.5159 0.1438 0.022 Uiso 1 1 calc R . . H6B H 0.5487 0.6293 0.1661 0.022 Uiso 1 1 calc R . . C7 C 0.6264(2) 0.4445(2) 0.12601(17) 0.0202(5) Uani 1 1 d . . . H7A H 0.6080 0.4640 0.0487 0.024 Uiso 1 1 calc R . . H7B H 0.7307 0.4646 0.1580 0.024 Uiso 1 1 calc R . . C8 C 0.5957(3) 0.2966(2) 0.14277(18) 0.0206(5) Uani 1 1 d . . . H8A H 0.6596 0.2401 0.1089 0.025 Uiso 1 1 calc R . . H8B H 0.4923 0.2758 0.1085 0.025 Uiso 1 1 calc R . . C9 C 0.6243(2) 0.2642(2) 0.26212(17) 0.0189(4) Uani 1 1 d . . . H9A H 0.5987 0.1693 0.2719 0.023 Uiso 1 1 calc R . . H9B H 0.7298 0.2766 0.2950 0.023 Uiso 1 1 calc R . . C10 C 0.5328(2) 0.3559(2) 0.31700(16) 0.0135(4) Uani 1 1 d . . . H10A H 0.4267 0.3350 0.2881 0.016 Uiso 1 1 calc R . . C11 C 0.1064(3) 0.5018(2) 0.3816(2) 0.0172(5) Uani 1 1 d . . . O1 O 0.15727(18) 0.5444(2) 0.47526(14) 0.0260(4) Uani 1 1 d . . . O2 O -0.02701(19) 0.4429(2) 0.36196(14) 0.0266(4) Uani 1 1 d D . . O3 O 0.1663(2) 0.50940(18) 0.30471(15) 0.0258(4) Uani 1 1 d . . . H1O H -0.061(3) 0.451(4) 0.4148(16) 0.032(8) 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 0.0174(2) 0.0149(2) 0.0142(2) -0.00010(13) 0.00279(16) 0.00005(13) N1 0.0145(8) 0.0130(8) 0.0114(8) 0.0002(7) 0.0033(6) 0.0000(7) N2 0.0145(8) 0.0118(8) 0.0117(8) -0.0003(7) 0.0030(6) -0.0001(6) C1 0.0254(11) 0.0137(10) 0.0153(10) 0.0014(8) 0.0061(8) -0.0010(8) C2 0.0264(11) 0.0129(10) 0.0183(10) 0.0030(8) 0.0041(9) 0.0049(8) C3 0.0231(11) 0.0107(9) 0.0173(10) 0.0010(8) 0.0083(8) -0.0009(8) C4 0.0247(11) 0.0208(11) 0.0214(11) -0.0016(9) 0.0058(9) -0.0082(9) C5 0.0127(10) 0.0151(10) 0.0100(9) 0.0000(7) 0.0024(8) 0.0002(7) C6 0.0190(10) 0.0245(11) 0.0113(10) 0.0016(9) 0.0036(8) 0.0015(9) C7 0.0194(10) 0.0295(13) 0.0125(10) 0.0004(9) 0.0054(8) 0.0014(9) C8 0.0206(11) 0.0268(12) 0.0151(10) -0.0067(9) 0.0055(8) 0.0001(9) C9 0.0208(10) 0.0193(10) 0.0171(10) -0.0033(8) 0.0057(8) 0.0014(8) C10 0.0136(9) 0.0153(10) 0.0112(9) -0.0024(7) 0.0017(7) -0.0009(7) C11 0.0128(10) 0.0164(11) 0.0203(11) -0.0002(8) -0.0003(9) 0.0000(7) O1 0.0174(8) 0.0406(11) 0.0185(8) -0.0033(8) 0.0009(6) -0.0096(8) O2 0.0188(8) 0.0375(11) 0.0231(9) -0.0095(8) 0.0042(7) -0.0113(8) O3 0.0183(9) 0.0386(11) 0.0208(9) -0.0047(7) 0.0048(7) -0.0050(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N2 1.9472(17) . ? Ni1 N2 1.9472(17) 3_666 ? Ni1 N1 1.9643(17) . ? Ni1 N1 1.9643(17) 3_666 ? N1 C1 1.484(3) . ? N1 C5 1.493(3) . ? N2 C3 1.491(3) 3_666 ? N2 C10 1.491(3) . ? C1 C2 1.514(3) . ? C2 C3 1.524(3) . ? C3 N2 1.491(3) 3_666 ? C3 C4 1.521(3) . ? C5 C10 1.516(3) . ? C5 C6 1.529(3) . ? C6 C7 1.529(3) . ? C7 C8 1.526(3) . ? C8 C9 1.532(3) . ? C9 C10 1.528(3) . ? C11 O3 1.244(3) . ? C11 O1 1.265(3) . ? C11 O2 1.350(3) . ? 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 180.00(9) . 3_666 ? N2 Ni1 N1 86.06(7) . . ? N2 Ni1 N1 93.94(7) 3_666 . ? N2 Ni1 N1 93.94(7) . 3_666 ? N2 Ni1 N1 86.06(7) 3_666 3_666 ? N1 Ni1 N1 180.0 . 3_666 ? C1 N1 C5 110.90(16) . . ? C1 N1 Ni1 122.89(13) . . ? C5 N1 Ni1 106.57(12) . . ? C3 N2 C10 113.02(16) 3_666 . ? C3 N2 Ni1 119.52(13) 3_666 . ? C10 N2 Ni1 110.16(12) . . ? N1 C1 C2 112.67(18) . . ? C1 C2 C3 114.46(18) . . ? N2 C3 C4 110.62(18) 3_666 . ? N2 C3 C2 108.26(17) 3_666 . ? C4 C3 C2 113.79(19) . . ? N1 C5 C10 106.14(17) . . ? N1 C5 C6 115.12(17) . . ? C10 C5 C6 111.39(18) . . ? C7 C6 C5 109.13(18) . . ? C8 C7 C6 110.41(19) . . ? C7 C8 C9 110.41(18) . . ? C10 C9 C8 110.30(18) . . ? N2 C10 C5 105.58(16) . . ? N2 C10 C9 114.02(17) . . ? C5 C10 C9 112.06(18) . . ? O3 C11 O1 126.7(2) . . ? O3 C11 O2 116.1(2) . . ? O1 C11 O2 117.3(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.93 1.92 2.814(3) 161.8 . N2 H2 O1 0.93 2.01 2.834(2) 146.1 3_666 O2 H1O O1 0.819(5) 1.836(7) 2.651(3) 173(4) 3_566 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.457 _refine_diff_density_min -0.918 _refine_diff_density_rms 0.094