#------------------------------------------------------------------------------ #$Date: 2011-01-02 22:00:31 +0200 (Sun, 02 Jan 2011) $ #$Revision: 5310 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2216642.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2216642 loop_ _publ_author_name 'Zhang, Min' 'Song, Xuegang' 'Su, Ping' 'Meng, Xianggao' _publ_section_title ;\ Diaqua[N,N'-bis(4-methoxybenzyl)-2,2'-(ethane-1,2-diyldiimino)\ diacetato]nickel(II) sesquihydrate ; _journal_coeditor_code LH2570 _journal_issue 12 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first m3164 _journal_page_last m3164 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac '[Ni (C22 H26 N2 O6) (H2 O)2], 1.5H2 O' _chemical_formula_moiety 'C22 H30 N2 Ni O8, 1.5(H2 O)' _chemical_formula_sum 'C22 H33 N2 Ni O9.5' _chemical_formula_weight 536.20 _chemical_name_systematic ; Diaqua[N,N'-bis(4-methoxybenzyl)-2,2'-(ethane-1,2- diyldiimino)diacetato]nickel(II) sesquihydrate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 114.248(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 25.1393(14) _cell_length_b 8.1256(4) _cell_length_c 26.6925(15) _cell_measurement_reflns_used 5321 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 26.88 _cell_measurement_theta_min 1.56 _cell_volume 4971.5(5) _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus (Bruker, 2001)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '0.3\% wide \w exposures' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine focus sealed Siemens Mo tube' _diffrn_radiation_type 'Mo k\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 26930 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.67 _exptl_absorpt_coefficient_mu 0.835 _exptl_absorpt_correction_type none _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2264 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.447 _refine_diff_density_min -0.360 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 337 _refine_ls_number_reflns 5429 _refine_ls_number_restraints 9 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0429 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0925P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1282 _refine_ls_wR_factor_ref 0.1329 _reflns_number_gt 4279 _reflns_number_total 5429 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh2570.cif _[local]_cod_cif_authors_sg_H-M 'C 2/c' _[local]_cod_cif_authors_sg_Hall '-C 2yc ' _[local]_cod_chemical_formula_sum_orig 'C22 H33 N2 Ni1 O9.5' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 2216642 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy Ni Ni 0.177788(10) 0.49923(3) 0.223662(10) 0.03190(12) Uani d . 1 C C1 0.08623(9) 0.5097(2) 0.26158(10) 0.0371(5) Uani d . 1 H H1A 0.0816 0.6283 0.2595 0.044 Uiso calc R 1 H H1B 0.0669 0.4671 0.2838 0.044 Uiso calc R 1 C C2 0.05859(9) 0.4373(3) 0.20478(9) 0.0388(5) Uani d . 1 H H2A 0.0611 0.3182 0.2072 0.047 Uiso calc R 1 H H2B 0.0176 0.4673 0.1879 0.047 Uiso calc R 1 C C3 0.18198(9) 0.5916(3) 0.32888(8) 0.0384(5) Uani d . 1 H H3A 0.2204 0.5493 0.3520 0.046 Uiso calc R 1 H H3B 0.1616 0.6145 0.3521 0.046 Uiso calc R 1 C C4 0.18819(9) 0.7496(3) 0.30125(9) 0.0395(5) Uani d . 1 C C5 0.16049(9) 0.2968(3) 0.31155(9) 0.0384(5) Uani d . 1 H H5A 0.2017 0.2727 0.3239 0.046 Uiso calc R 1 H H5B 0.1393 0.2194 0.2825 0.046 Uiso calc R 1 C C6 0.14326(9) 0.2674(3) 0.35899(9) 0.0375(5) Uani d . 1 C C7 0.08884(9) 0.2062(3) 0.35051(9) 0.0406(5) Uani d . 1 H H7 0.0621 0.1847 0.3148 0.049 Uiso calc R 1 C C8 0.07307(10) 0.1761(3) 0.39378(9) 0.0406(5) Uani d . 1 H H8 0.0363 0.1348 0.3871 0.049 Uiso calc R 1 C C9 0.11248(10) 0.2080(3) 0.44652(9) 0.0472(6) Uani d . 1 C C10 0.16688(11) 0.2712(4) 0.45653(11) 0.0611(8) Uani d . 1 H H10 0.1931 0.2955 0.4922 0.073 Uiso calc R 1 C C11 0.18194(10) 0.2981(4) 0.41266(10) 0.0549(7) Uani d . 1 H H11 0.2190 0.3378 0.4195 0.066 Uiso calc R 1 C C12 0.05006(11) 0.0964(4) 0.48656(11) 0.0599(7) Uani d . 1 H H12A 0.0169 0.1655 0.4674 0.090 Uiso calc R 1 H H12B 0.0516 0.0699 0.5222 0.090 Uiso calc R 1 H H12C 0.0466 -0.0030 0.4661 0.090 Uiso calc R 1 C C13 0.08348(9) 0.3750(3) 0.12824(9) 0.0415(5) Uani d . 1 H H13A 0.0920 0.4271 0.0997 0.050 Uiso calc R 1 H H13B 0.0438 0.3336 0.1116 0.050 Uiso calc R 1 C C14 0.12553(9) 0.2309(3) 0.15258(10) 0.0423(5) Uani d . 1 C C15 0.06626(9) 0.6627(3) 0.14556(9) 0.0392(5) Uani d . 1 H H15A 0.0872 0.6943 0.1236 0.047 Uiso calc R 1 H H15B 0.0761 0.7420 0.1752 0.047 Uiso calc R 1 C C16 0.00181(9) 0.6764(3) 0.11018(9) 0.0394(5) Uani d . 1 C C17 -0.02254(10) 0.6239(4) 0.05617(9) 0.0529(6) Uani d . 1 H H17 0.0016 0.5790 0.0411 0.063 Uiso calc R 1 C C18 -0.08187(11) 0.6362(4) 0.02370(10) 0.0601(7) Uani d . 1 H H18 -0.0972 0.5967 -0.0122 0.072 Uiso calc R 1 C C19 -0.11784(10) 0.7070(3) 0.04483(11) 0.0532(6) Uani d . 1 C C20 -0.09445(10) 0.7631(3) 0.09848(10) 0.0481(6) Uani d . 1 H H20 -0.1185 0.8121 0.1129 0.058 Uiso calc R 1 C C21 -0.03585(10) 0.7467(3) 0.13052(9) 0.0426(5) Uani d . 1 H H21 -0.0209 0.7835 0.1667 0.051 Uiso calc R 1 C C22 -0.20177(13) 0.6894(6) -0.04023(13) 0.1024(14) Uani d . 1 H H22A -0.1866 0.7626 -0.0594 0.154 Uiso calc R 1 H H22B -0.2434 0.7019 -0.0543 0.154 Uiso calc R 1 H H22C -0.1925 0.5779 -0.0455 0.154 Uiso calc R 1 N N1 0.14956(7) 0.4672(2) 0.28780(7) 0.0312(4) Uani d . 1 N N2 0.08809(8) 0.49765(18) 0.17022(8) 0.0331(4) Uani d . 1 O O1 0.18227(6) 0.73640(17) 0.25161(6) 0.0361(3) Uani d . 1 O O2 0.19946(9) 0.8785(2) 0.32799(8) 0.0633(5) Uani d . 1 O O3 0.10204(8) 0.1810(3) 0.49259(7) 0.0660(6) Uani d . 1 O O4 0.16957(6) 0.25788(17) 0.19711(6) 0.0363(3) Uani d . 1 O O5 0.11420(8) 0.0997(2) 0.12718(8) 0.0753(6) Uani d . 1 O O6 -0.17656(7) 0.7273(3) 0.01645(9) 0.0784(7) Uani d . 1 O O7 0.26310(6) 0.47501(19) 0.27647(6) 0.0326(3) Uani d D 1 H H7A 0.2796(10) 0.560(2) 0.2818(11) 0.049 Uiso d D 1 H H7B 0.2772(10) 0.405(2) 0.2679(10) 0.049 Uiso d D 1 O O8 0.20131(7) 0.5574(2) 0.15954(7) 0.0425(4) Uani d D 1 H H8B 0.2297(10) 0.519(3) 0.1597(13) 0.064 Uiso d D 1 H H8A 0.1971(12) 0.653(2) 0.1477(11) 0.064 Uiso d D 1 O O10 0.18169(8) 0.8511(2) 0.10513(7) 0.0541(4) Uani d D 1 H H10A 0.1592(12) 0.836(4) 0.0748(8) 0.081 Uiso d D 1 H H10B 0.1741(14) 0.932(3) 0.1176(12) 0.081 Uiso d D 1 O O9 0.0732(2) 0.9932(4) 0.2293(2) 0.0868(16) Uani d P 0.50 H H9A 0.1124 0.9932 0.2293 0.130 Uiso d PR 0.50 H H9B 0.0502 0.9984 0.1962 0.130 Uiso d PR 0.50 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 0.02839(18) 0.03414(19) 0.03438(18) 0.00004(9) 0.01411(13) 0.00305(9) C1 0.0288(11) 0.0420(13) 0.0468(12) 0.0068(8) 0.0222(10) 0.0130(9) C2 0.0260(10) 0.0412(12) 0.0497(12) -0.0009(9) 0.0161(9) 0.0099(10) C3 0.0419(12) 0.0422(13) 0.0375(10) 0.0029(9) 0.0226(9) 0.0001(9) C4 0.0372(11) 0.0392(12) 0.0495(12) 0.0011(9) 0.0253(10) -0.0020(10) C5 0.0367(11) 0.0394(12) 0.0442(11) 0.0068(9) 0.0216(9) 0.0133(9) C6 0.0357(10) 0.0391(12) 0.0402(11) 0.0039(9) 0.0180(9) 0.0125(9) C7 0.0388(11) 0.0430(13) 0.0394(11) -0.0021(9) 0.0155(9) 0.0066(9) C8 0.0370(11) 0.0430(13) 0.0447(12) -0.0031(9) 0.0198(10) 0.0070(10) C9 0.0458(13) 0.0592(16) 0.0408(12) -0.0032(11) 0.0221(10) 0.0111(11) C10 0.0466(14) 0.091(2) 0.0383(12) -0.0185(14) 0.0104(10) 0.0138(13) C11 0.0364(12) 0.0805(19) 0.0439(12) -0.0084(12) 0.0126(10) 0.0180(12) C12 0.0507(15) 0.086(2) 0.0526(14) -0.0012(14) 0.0313(12) 0.0142(14) C13 0.0344(11) 0.0452(13) 0.0367(10) 0.0014(9) 0.0063(9) 0.0016(9) C14 0.0348(11) 0.0406(13) 0.0464(12) -0.0011(9) 0.0116(9) -0.0044(10) C15 0.0335(11) 0.0382(12) 0.0449(11) 0.0045(9) 0.0151(9) 0.0132(9) C16 0.0348(11) 0.0415(12) 0.0416(11) 0.0070(9) 0.0154(9) 0.0128(9) C17 0.0433(13) 0.0733(18) 0.0426(12) 0.0167(12) 0.0181(10) 0.0102(12) C18 0.0486(14) 0.085(2) 0.0395(12) 0.0121(14) 0.0111(11) 0.0049(13) C19 0.0351(12) 0.0685(18) 0.0529(14) 0.0058(11) 0.0147(11) 0.0116(12) C20 0.0387(12) 0.0538(15) 0.0579(14) 0.0095(10) 0.0259(11) 0.0125(12) C21 0.0418(12) 0.0451(13) 0.0419(11) 0.0041(10) 0.0183(10) 0.0077(10) C22 0.0467(17) 0.175(4) 0.0621(19) 0.011(2) -0.0008(15) 0.016(2) N1 0.0263(8) 0.0344(9) 0.0362(9) 0.0035(7) 0.0162(7) 0.0067(7) N2 0.0276(9) 0.0344(10) 0.0373(9) 0.0029(6) 0.0132(8) 0.0078(7) O1 0.0374(8) 0.0330(8) 0.0426(8) -0.0016(6) 0.0210(6) 0.0019(6) O2 0.0919(14) 0.0448(10) 0.0778(12) -0.0143(9) 0.0598(11) -0.0192(9) O3 0.0639(11) 0.0989(15) 0.0404(9) -0.0248(11) 0.0267(8) 0.0083(9) O4 0.0310(7) 0.0343(8) 0.0388(8) 0.0017(6) 0.0097(6) 0.0007(6) O5 0.0577(11) 0.0523(12) 0.0821(13) 0.0061(9) -0.0056(10) -0.0270(10) O6 0.0323(9) 0.126(2) 0.0665(12) 0.0121(10) 0.0096(9) 0.0082(12) O7 0.0276(8) 0.0343(8) 0.0361(8) 0.0007(6) 0.0134(6) -0.0032(6) O8 0.0422(9) 0.0480(9) 0.0447(9) 0.0053(8) 0.0254(7) 0.0098(8) O10 0.0628(11) 0.0548(11) 0.0409(9) 0.0101(9) 0.0176(8) 0.0019(8) O9 0.066(3) 0.066(3) 0.115(4) 0.0022(19) 0.023(3) -0.020(2) 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O7 Ni O1 87.37(6) no O7 Ni O4 94.26(6) no O1 Ni O4 176.70(5) no O7 Ni O8 90.98(6) no O1 Ni O8 95.39(6) no O4 Ni O8 87.46(7) no O7 Ni N2 173.93(6) no O1 Ni N2 97.76(6) no O4 Ni N2 80.46(6) no O8 Ni N2 91.78(7) no O7 Ni N1 92.06(6) no O1 Ni N1 78.96(6) no O4 Ni N1 98.10(6) no O8 Ni N1 173.46(6) no N2 Ni N1 85.77(7) no N1 C1 C2 110.15(17) no N1 C1 H1A 109.6 no C2 C1 H1A 109.6 no N1 C1 H1B 109.6 no C2 C1 H1B 109.6 no H1A C1 H1B 108.1 no N2 C2 C1 110.81(17) no N2 C2 H2A 109.5 no C1 C2 H2A 109.5 no N2 C2 H2B 109.5 no C1 C2 H2B 109.5 no H2A C2 H2B 108.1 no N1 C3 C4 110.80(17) no N1 C3 H3A 109.5 no C4 C3 H3A 109.5 no N1 C3 H3B 109.5 no C4 C3 H3B 109.5 no H3A C3 H3B 108.1 no O2 C4 O1 125.0(2) no O2 C4 C3 118.8(2) no O1 C4 C3 116.18(19) no N1 C5 C6 115.65(17) no N1 C5 H5A 108.4 no C6 C5 H5A 108.4 no N1 C5 H5B 108.4 no C6 C5 H5B 108.4 no H5A C5 H5B 107.4 no C11 C6 C7 117.5(2) no C11 C6 C5 121.1(2) no C7 C6 C5 121.5(2) no C6 C7 C8 121.9(2) no C6 C7 H7 119.1 no C8 C7 H7 119.1 no C9 C8 C7 119.2(2) no C9 C8 H8 120.4 no C7 C8 H8 120.4 no C8 C9 O3 124.3(2) no C8 C9 C10 120.6(2) no O3 C9 C10 115.1(2) no C9 C10 C11 119.1(2) no C9 C10 H10 120.4 no C11 C10 H10 120.4 no C6 C11 C10 121.7(2) no C6 C11 H11 119.1 no C10 C11 H11 119.1 no O3 C12 H12A 109.5 no O3 C12 H12B 109.5 no H12A C12 H12B 109.5 no O3 C12 H12C 109.5 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no N2 C13 C14 111.77(17) no N2 C13 H13A 109.3 no C14 C13 H13A 109.3 no N2 C13 H13B 109.3 no C14 C13 H13B 109.3 no H13A C13 H13B 107.9 no O5 C14 O4 125.5(2) no O5 C14 C13 117.7(2) no O4 C14 C13 116.77(19) no N2 C15 C16 116.57(18) no N2 C15 H15A 108.1 no C16 C15 H15A 108.1 no N2 C15 H15B 108.1 no C16 C15 H15B 108.1 no H15A C15 H15B 107.3 no C17 C16 C21 116.9(2) no C17 C16 C15 122.2(2) no C21 C16 C15 120.9(2) no C16 C17 C18 122.1(2) no C16 C17 H17 118.9 no C18 C17 H17 118.9 no C19 C18 C17 119.6(2) no C19 C18 H18 120.2 no C17 C18 H18 120.2 no O6 C19 C18 124.6(2) no O6 C19 C20 116.0(2) no C18 C19 C20 119.5(2) no C21 C20 C19 120.3(2) no C21 C20 H20 119.9 no C19 C20 H20 119.9 no C20 C21 C16 121.6(2) no C20 C21 H21 119.2 no C16 C21 H21 119.2 no O6 C22 H22A 109.5 no O6 C22 H22B 109.5 no H22A C22 H22B 109.5 no O6 C22 H22C 109.5 no H22A C22 H22C 109.5 no H22B C22 H22C 109.5 no C3 N1 C1 110.43(16) no C3 N1 C5 111.74(16) no C1 N1 C5 112.73(16) no C3 N1 Ni 104.56(12) no C1 N1 Ni 103.84(12) no C5 N1 Ni 112.98(12) no C13 N2 C2 110.31(16) no C13 N2 C15 111.92(17) no C2 N2 C15 112.52(17) no C13 N2 Ni 104.29(12) no C2 N2 Ni 104.43(12) no C15 N2 Ni 112.83(12) no C4 O1 Ni 114.97(13) no C9 O3 C12 118.57(19) no C14 O4 Ni 114.31(14) no C19 O6 C22 118.4(2) no Ni O7 H7A 111.5(19) no Ni O7 H7B 110.9(19) no H7A O7 H7B 116(2) no Ni O8 H8B 118(2) no Ni O8 H8A 119.4(19) no H8B O8 H8A 110(2) no H10A O10 H10B 112(3) no H9A O9 H9B 105.1 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Ni O7 2.0352(15) yes Ni O1 2.0529(14) yes Ni O4 2.0666(14) yes Ni O8 2.0818(15) yes Ni N2 2.1159(18) yes Ni N1 2.1212(17) yes C1 N1 1.493(3) no C1 C2 1.504(3) no C1 H1A 0.9700 no C1 H1B 0.9700 no C2 N2 1.484(3) no C2 H2A 0.9700 no C2 H2B 0.9700 no C3 N1 1.468(3) no C3 C4 1.521(3) no C3 H3A 0.9700 no C3 H3B 0.9700 no C4 O2 1.233(3) no C4 O1 1.276(3) no C5 N1 1.500(3) no C5 C6 1.516(3) no C5 H5A 0.9700 no C5 H5B 0.9700 no C6 C11 1.384(3) no C6 C7 1.384(3) no C7 C8 1.388(3) no C7 H7 0.9300 no C8 C9 1.373(3) no C8 H8 0.9300 no C9 O3 1.376(3) no C9 C10 1.380(3) no C10 C11 1.388(4) no C10 H10 0.9300 no C11 H11 0.9300 no C12 O3 1.426(3) no C12 H12A 0.9600 no C12 H12B 0.9600 no C12 H12C 0.9600 no C13 N2 1.468(3) no C13 C14 1.532(3) no C13 H13A 0.9700 no C13 H13B 0.9700 no C14 O5 1.232(3) no C14 O4 1.267(3) no C15 N2 1.496(3) no C15 C16 1.508(3) no C15 H15A 0.9700 no C15 H15B 0.9700 no C16 C17 1.382(3) no C16 C21 1.393(3) no C17 C18 1.387(3) no C17 H17 0.9300 no C18 C19 1.373(4) no C18 H18 0.9300 no C19 O6 1.364(3) no C19 C20 1.383(4) no C20 C21 1.373(3) no C20 H20 0.9300 no C21 H21 0.9300 no C22 O6 1.413(4) no C22 H22A 0.9600 no C22 H22B 0.9600 no C22 H22C 0.9600 no O7 H7A 0.791(15) no O7 H7B 0.757(15) no O8 H8B 0.776(17) no O8 H8A 0.832(16) no O10 H10A 0.784(17) no O10 H10B 0.796(17) no O9 H9A 0.9830 no O9 H9B 0.8345 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O7 H7A O4 4 0.791(15) 1.984(16) 2.769(2) 172(3) yes O7 H7B O1 4_545 0.757(15) 1.900(16) 2.656(2) 176(2) yes O8 H8B O2 4_545 0.776(17) 2.027(16) 2.787(2) 166(3) yes O10 H10A O3 6_565 0.784(17) 2.076(17) 2.857(2) 174(3) yes O10 H10B O5 1_565 0.796(17) 2.12(2) 2.851(3) 152(3) yes C5 H5B O9 1_545 0.97 2.49 3.430(5) 162.1 yes C15 H15B O9 . 0.97 2.52 3.451(5) 161.4 yes O8 H8A O10 . 0.832(16) 1.913(17) 2.731(3) 167(3) yes C12 H12C Cg1 2_545 0.96 2.80 3.746(3) 169 yes 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_publ_flag N1 C1 C2 N2 -58.1(2) no N1 C3 C4 O2 160.3(2) no N1 C3 C4 O1 -21.0(3) no N1 C5 C6 C11 -88.3(3) no N1 C5 C6 C7 92.9(3) no C11 C6 C7 C8 0.0(3) no C5 C6 C7 C8 178.8(2) no C6 C7 C8 C9 0.1(4) no C7 C8 C9 O3 -179.1(2) no C7 C8 C9 C10 0.8(4) no C8 C9 C10 C11 -1.7(5) no O3 C9 C10 C11 178.2(3) no C7 C6 C11 C10 -0.9(4) no C5 C6 C11 C10 -179.7(3) no C9 C10 C11 C6 1.8(5) no N2 C13 C14 O5 158.0(2) no N2 C13 C14 O4 -22.7(3) no N2 C15 C16 C17 -80.1(3) no N2 C15 C16 C21 101.4(3) no C21 C16 C17 C18 -1.6(4) no C15 C16 C17 C18 179.8(2) no C16 C17 C18 C19 2.0(4) no C17 C18 C19 O6 179.1(3) no C17 C18 C19 C20 -0.9(4) no O6 C19 C20 C21 179.4(2) no C18 C19 C20 C21 -0.6(4) no C19 C20 C21 C16 1.0(4) no C17 C16 C21 C20 0.1(3) no C15 C16 C21 C20 178.7(2) no C4 C3 N1 C1 -73.8(2) no C4 C3 N1 C5 159.87(16) no C4 C3 N1 Ni 37.33(18) no C2 C1 N1 C3 153.48(17) no C2 C1 N1 C5 -80.7(2) no C2 C1 N1 Ni 41.88(18) no C6 C5 N1 C3 60.3(2) no C6 C5 N1 C1 -64.7(2) no C6 C5 N1 Ni 177.91(14) no O7 Ni N1 C3 54.35(12) no O1 Ni N1 C3 -32.57(12) no O4 Ni N1 C3 148.95(12) no N2 Ni N1 C3 -131.33(13) no O7 Ni N1 C1 170.16(12) no O1 Ni N1 C1 83.25(12) no O4 Ni N1 C1 -95.24(12) no N2 Ni N1 C1 -15.52(12) no O7 Ni N1 C5 -67.38(14) no O1 Ni N1 C5 -154.29(14) no O4 Ni N1 C5 27.22(14) no N2 Ni N1 C5 106.94(14) no C14 C13 N2 C2 -76.0(2) no C14 C13 N2 C15 157.91(18) no C14 C13 N2 Ni 35.6(2) no C1 C2 N2 C13 151.50(17) no C1 C2 N2 C15 -82.7(2) no C1 C2 N2 Ni 39.97(19) no C16 C15 N2 C13 67.1(2) no C16 C15 N2 C2 -57.8(2) no C16 C15 N2 Ni -175.64(15) no O1 Ni N2 C13 153.15(13) no O4 Ni N2 C13 -29.66(13) no O8 Ni N2 C13 57.46(13) no N1 Ni N2 C13 -128.61(13) no O1 Ni N2 C2 -91.04(13) no O4 Ni N2 C2 86.15(13) no O8 Ni N2 C2 173.27(13) no N1 Ni N2 C2 -12.80(13) no O4 Ni N2 C15 -151.34(15) no O8 Ni N2 C15 -64.22(15) no N1 Ni N2 C15 109.71(15) no O2 C4 O1 Ni 169.82(19) no C3 C4 O1 Ni -8.7(2) no O8 Ni O1 C4 -159.23(15) no N2 Ni O1 C4 108.24(15) no N1 Ni O1 C4 24.12(14) no C8 C9 O3 C12 7.9(4) no C10 C9 O3 C12 -172.0(3) no O5 C14 O4 Ni 174.6(2) no C13 C14 O4 Ni -4.6(3) no O7 Ni O4 C14 -162.88(15) no O8 Ni O4 C14 -72.09(15) no N2 Ni O4 C14 20.14(15) no N1 Ni O4 C14 104.43(15) no C18 C19 O6 C22 -7.0(5) no C20 C19 O6 C22 173.0(3) no