#------------------------------------------------------------------------------ #$Date: 2021-09-06 15:01:16 +0300 (Mon, 06 Sep 2021) $ #$Revision: 268858 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/07/7060707.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7060707 loop_ _publ_author_name 'Jagtap, Rahul A.' 'Ankade, Shidheshwar B.' 'Gonnade, Rajesh G.' 'Punji, Benudhar' _publ_section_title ; Achiral and chiral NNN-pincer nickel complexes with oxazolinyl backbones: application in transfer hydrogenation of ketones ; _journal_issue 27 _journal_name_full 'New Journal of Chemistry' _journal_page_first 11927 _journal_page_last 11936 _journal_paper_doi 10.1039/D1NJ01698A _journal_volume 45 _journal_year 2021 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C22 H26 Cl N3 Ni O2' _chemical_formula_sum 'C22 H26 Cl N3 Ni O2' _chemical_formula_weight 458.62 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-03-29 deposited with the CCDC. 2021-05-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.9695(4) _cell_length_b 10.0137(3) _cell_length_c 21.4431(7) _cell_measurement_reflns_used 9954 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 33.71 _cell_measurement_theta_min 2.25 _cell_volume 2140.70(13) _computing_cell_refinement 'SAINT (Bruker, 2016)' _computing_data_collection 'APEX3 (Bruker, 2016)' _computing_data_reduction 'SAINT (Bruker, 2016)' _computing_molecular_graphics 'Bruker SHELXTL, Mercury 2020.20' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Photon II CPAD Area Detector' _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.952 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'multilayer mirrors' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_unetI/netI 0.0349 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.952 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 44424 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.916 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 34.629 _diffrn_reflns_theta_min 2.245 _diffrn_source 'micro-focus sealed tube' _diffrn_source_type 'Incoatech I\mS HB' _exptl_absorpt_coefficient_mu 1.054 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_correction_T_min 0.809 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (BRUKER, 2016)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.423 _exptl_crystal_description plate _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.254 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.052 _refine_ls_abs_structure_details ; Flack x determined using 2969 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.008(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 8381 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0264 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+0.1125P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.0585 _reflns_Friedel_coverage 0.730 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.870 _reflns_number_gt 7601 _reflns_number_total 8381 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01698a2.cif _cod_data_source_block RJ-D-57 _cod_depositor_comments 'Adding full bibliography for 7060706--7060708.cif.' _cod_database_code 7060707 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.809 _shelx_estimated_absorpt_t_max 0.969 _shelx_res_file ; TITL rjd_a.res in P2(1)2(1)2(1) rjd.res created by SHELXL-2018/3 at 22:46:47 on 29-Mar-2021 CELL 0.71073 9.9695 10.0137 21.4431 90.000 90.000 90.000 ZERR 4.00 0.0004 0.0003 0.0007 0.000 0.000 0.000 LATT -1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O Cl Ni UNIT 88 104 12 8 4 4 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 30 ACTA OMIT 1 0 1 OMIT 0 0 6 OMIT 0 2 9 BOND $H FMAP 2 PLAN 2 SIZE 0.21 0.15 0.03 CONF TEMP -173.00 WGHT 0.025800 0.112500 FVAR 0.70522 NI1 6 0.256179 0.406626 0.325995 11.00000 0.02087 0.01567 = 0.01825 0.00096 0.00328 0.00100 CL1 5 0.162882 0.360649 0.415911 11.00000 0.03370 0.02302 = 0.02429 0.00181 0.01000 -0.00030 O1 4 0.114184 0.777631 0.286915 11.00000 0.04202 0.02124 = 0.03065 -0.00089 -0.00430 0.00979 O2 4 0.501148 0.360732 0.183087 11.00000 0.03367 0.03561 = 0.02990 0.00394 0.01403 0.00673 N1 3 0.178223 0.578696 0.324678 11.00000 0.02353 0.01754 = 0.02142 -0.00166 0.00151 0.00176 N2 3 0.319268 0.425986 0.243740 11.00000 0.02324 0.01998 = 0.01908 0.00213 0.00342 0.00270 N3 3 0.358730 0.239540 0.327547 11.00000 0.02530 0.01896 = 0.02172 0.00191 0.00238 0.00252 C1 1 0.154271 0.663049 0.381130 11.00000 0.02569 0.01855 = 0.02421 -0.00342 0.00318 0.00173 AFIX 13 H1 2 0.093755 0.616220 0.411213 11.00000 -1.20000 AFIX 0 C2 1 0.084698 0.785166 0.353279 11.00000 0.04327 0.02821 = 0.03120 -0.00775 -0.00413 0.01326 AFIX 23 H2A 2 -0.013225 0.781697 0.360776 11.00000 -1.20000 H2AB 2 0.120802 0.868595 0.371497 11.00000 -1.20000 AFIX 0 C3 1 0.159296 0.652480 0.276377 11.00000 0.02334 0.01919 = 0.02790 -0.00024 -0.00015 0.00330 C4 1 0.179790 0.615506 0.211904 11.00000 0.02691 0.02176 = 0.02334 0.00282 -0.00106 0.00067 C5 1 0.118333 0.691498 0.164999 11.00000 0.03584 0.03005 = 0.02942 0.00698 -0.00268 0.00636 AFIX 43 H5 2 0.066997 0.767859 0.176022 11.00000 -1.20000 AFIX 0 C6 1 0.131486 0.656753 0.103031 11.00000 0.04480 0.04148 = 0.02718 0.01113 -0.00560 0.00487 AFIX 43 H6 2 0.090517 0.709043 0.071349 11.00000 -1.20000 AFIX 0 C7 1 0.205414 0.544386 0.087843 11.00000 0.04364 0.04390 = 0.02138 0.00378 0.00002 0.00168 AFIX 43 H7 2 0.213290 0.518696 0.045353 11.00000 -1.20000 AFIX 0 C8 1 0.267940 0.468881 0.133185 11.00000 0.03413 0.03115 = 0.02221 0.00113 0.00288 0.00084 AFIX 43 H8 2 0.318311 0.392439 0.121354 11.00000 -1.20000 AFIX 0 C9 1 0.258282 0.503267 0.196563 11.00000 0.02367 0.02142 = 0.02171 0.00230 0.00170 -0.00078 C10 1 0.429446 0.352594 0.229646 11.00000 0.02412 0.02203 = 0.02411 -0.00026 0.00439 0.00055 C11 1 0.465893 0.253493 0.279848 11.00000 0.02625 0.02639 = 0.02819 0.00420 0.00591 0.00678 AFIX 23 H11A 2 0.482817 0.165363 0.260462 11.00000 -1.20000 H11B 2 0.549772 0.282685 0.300462 11.00000 -1.20000 AFIX 0 C12 1 0.268306 0.123399 0.311942 11.00000 0.03518 0.01745 = 0.03223 0.00032 0.00436 -0.00001 AFIX 23 H12A 2 0.197804 0.117187 0.344326 11.00000 -1.20000 H12B 2 0.321843 0.040234 0.313863 11.00000 -1.20000 AFIX 0 C13 1 0.201157 0.130798 0.248763 11.00000 0.04515 0.02954 = 0.03573 -0.00727 -0.00371 -0.00659 AFIX 137 H13A 2 0.269768 0.134051 0.216070 11.00000 -1.50000 H13B 2 0.145552 0.211367 0.246583 11.00000 -1.50000 H13C 2 0.144655 0.051770 0.242713 11.00000 -1.50000 AFIX 0 C14 1 0.424174 0.204646 0.388718 11.00000 0.03333 0.02731 = 0.02769 0.00681 -0.00124 0.00736 AFIX 23 H14A 2 0.483797 0.126837 0.382173 11.00000 -1.20000 H14B 2 0.353557 0.177418 0.418584 11.00000 -1.20000 AFIX 0 C15 1 0.505373 0.316528 0.417606 11.00000 0.03866 0.04634 = 0.03756 -0.00053 -0.00882 -0.00004 AFIX 137 H15A 2 0.577803 0.342236 0.389135 11.00000 -1.50000 H15B 2 0.543799 0.286112 0.457201 11.00000 -1.50000 H15C 2 0.447054 0.393626 0.425172 11.00000 -1.50000 AFIX 0 C16 1 0.289242 0.693332 0.411177 11.00000 0.02417 0.02211 = 0.02373 -0.00184 0.00480 -0.00194 AFIX 23 H16A 2 0.329277 0.608611 0.426002 11.00000 -1.20000 H16B 2 0.349865 0.730982 0.379114 11.00000 -1.20000 AFIX 0 C17 1 0.281393 0.789892 0.465389 11.00000 0.02469 0.01927 = 0.02274 0.00154 -0.00112 -0.00062 C18 1 0.188979 0.774686 0.513203 11.00000 0.03723 0.02799 = 0.02836 -0.00372 0.00713 -0.00851 AFIX 43 H18 2 0.125649 0.703911 0.511350 11.00000 -1.20000 AFIX 0 C19 1 0.187623 0.861695 0.563942 11.00000 0.04530 0.03700 = 0.02737 -0.00575 0.00829 -0.00144 AFIX 43 H19 2 0.123237 0.850911 0.596212 11.00000 -1.20000 AFIX 0 C20 1 0.280712 0.963790 0.566926 11.00000 0.04336 0.02833 = 0.02852 -0.00628 -0.00783 0.00492 AFIX 43 H20 2 0.282692 1.021295 0.602151 11.00000 -1.20000 AFIX 0 C21 1 0.370742 0.982332 0.518851 11.00000 0.03321 0.02312 = 0.03672 -0.00255 -0.01042 -0.00241 AFIX 43 H21 2 0.433095 1.053985 0.520503 11.00000 -1.20000 AFIX 0 C22 1 0.370310 0.896385 0.468061 11.00000 0.02299 0.02347 = 0.02838 0.00261 -0.00205 -0.00115 AFIX 43 H22 2 0.431539 0.910611 0.434770 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM rjd_a.res in P2(1)2(1)2(1) REM wR2 = 0.058466, GooF = S = 1.03572, Restrained GooF = 1.03572 for all data REM R1 = 0.026372 for 7601 Fo > 4sig(Fo) and 0.033772 for all 8381 data REM 264 parameters refined using 0 restraints END WGHT 0.0258 0.1125 REM Highest difference peak 0.254, deepest hole -0.369, 1-sigma level 0.052 Q1 1 0.2468 0.7651 0.4899 11.00000 0.05 0.25 Q2 1 0.3733 0.9152 0.4988 11.00000 0.05 0.25 ; _shelx_res_checksum 29203 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.25618(2) 0.40663(2) 0.32600(2) 0.01826(5) Uani 1 1 d . . . . . Cl1 Cl 0.16288(4) 0.36065(4) 0.41591(2) 0.02700(8) Uani 1 1 d . . . . . O1 O 0.11418(14) 0.77763(11) 0.28691(6) 0.0313(3) Uani 1 1 d . . . . . O2 O 0.50115(13) 0.36073(13) 0.18309(6) 0.0331(3) Uani 1 1 d . . . . . N1 N 0.17822(13) 0.57870(11) 0.32468(6) 0.0208(2) Uani 1 1 d . . . . . N2 N 0.31927(14) 0.42599(12) 0.24374(6) 0.0208(2) Uani 1 1 d . . . . . N3 N 0.35873(13) 0.23954(12) 0.32755(6) 0.0220(2) Uani 1 1 d . . . . . C1 C 0.15427(17) 0.66305(14) 0.38113(7) 0.0228(3) Uani 1 1 d . . . . . H1 H 0.093755 0.616220 0.411213 0.027 Uiso 1 1 calc R U . . . C2 C 0.0847(2) 0.78517(18) 0.35328(8) 0.0342(4) Uani 1 1 d . . . . . H2A H -0.013225 0.781697 0.360776 0.041 Uiso 1 1 calc R U . . . H2AB H 0.120802 0.868595 0.371497 0.041 Uiso 1 1 calc R U . . . C3 C 0.15930(17) 0.65248(14) 0.27638(7) 0.0235(3) Uani 1 1 d . . . . . C4 C 0.17979(17) 0.61551(15) 0.21190(7) 0.0240(3) Uani 1 1 d . . . . . C5 C 0.11833(19) 0.69150(17) 0.16500(8) 0.0318(4) Uani 1 1 d . . . . . H5 H 0.066997 0.767859 0.176022 0.038 Uiso 1 1 calc R U . . . C6 C 0.1315(2) 0.6568(2) 0.10303(9) 0.0378(4) Uani 1 1 d . . . . . H6 H 0.090517 0.709043 0.071349 0.045 Uiso 1 1 calc R U . . . C7 C 0.2054(2) 0.5444(2) 0.08784(8) 0.0363(4) Uani 1 1 d . . . . . H7 H 0.213290 0.518696 0.045353 0.044 Uiso 1 1 calc R U . . . C8 C 0.2679(2) 0.46888(17) 0.13319(7) 0.0292(3) Uani 1 1 d . . . . . H8 H 0.318311 0.392439 0.121354 0.035 Uiso 1 1 calc R U . . . C9 C 0.25828(18) 0.50327(13) 0.19656(7) 0.0223(3) Uani 1 1 d . . . . . C10 C 0.42945(17) 0.35259(15) 0.22965(7) 0.0234(3) Uani 1 1 d . . . . . C11 C 0.46589(18) 0.25349(16) 0.27985(8) 0.0269(3) Uani 1 1 d . . . . . H11A H 0.482817 0.165363 0.260462 0.032 Uiso 1 1 calc R U . . . H11B H 0.549772 0.282685 0.300462 0.032 Uiso 1 1 calc R U . . . C12 C 0.26831(19) 0.12340(14) 0.31194(8) 0.0283(3) Uani 1 1 d . . . . . H12A H 0.197804 0.117187 0.344326 0.034 Uiso 1 1 calc R U . . . H12B H 0.321843 0.040234 0.313863 0.034 Uiso 1 1 calc R U . . . C13 C 0.2012(2) 0.13080(19) 0.24876(9) 0.0368(4) Uani 1 1 d . . . . . H13A H 0.269768 0.134051 0.216070 0.055 Uiso 1 1 calc R U . . . H13B H 0.145552 0.211367 0.246583 0.055 Uiso 1 1 calc R U . . . H13C H 0.144655 0.051770 0.242713 0.055 Uiso 1 1 calc R U . . . C14 C 0.42417(19) 0.20465(17) 0.38872(8) 0.0294(4) Uani 1 1 d . . . . . H14A H 0.483797 0.126837 0.382173 0.035 Uiso 1 1 calc R U . . . H14B H 0.353557 0.177418 0.418584 0.035 Uiso 1 1 calc R U . . . C15 C 0.5054(2) 0.3165(2) 0.41761(10) 0.0409(4) Uani 1 1 d . . . . . H15A H 0.577803 0.342236 0.389135 0.061 Uiso 1 1 calc R U . . . H15B H 0.543799 0.286112 0.457201 0.061 Uiso 1 1 calc R U . . . H15C H 0.447054 0.393626 0.425172 0.061 Uiso 1 1 calc R U . . . C16 C 0.28924(16) 0.69333(15) 0.41118(8) 0.0233(3) Uani 1 1 d . . . . . H16A H 0.329277 0.608611 0.426002 0.028 Uiso 1 1 calc R U . . . H16B H 0.349865 0.730982 0.379114 0.028 Uiso 1 1 calc R U . . . C17 C 0.28139(16) 0.78989(14) 0.46539(7) 0.0222(3) Uani 1 1 d . . . . . C18 C 0.1890(2) 0.77469(17) 0.51320(8) 0.0312(4) Uani 1 1 d . . . . . H18 H 0.125649 0.703911 0.511350 0.037 Uiso 1 1 calc R U . . . C19 C 0.1876(2) 0.86170(19) 0.56394(9) 0.0366(4) Uani 1 1 d . . . . . H19 H 0.123237 0.850911 0.596212 0.044 Uiso 1 1 calc R U . . . C20 C 0.2807(2) 0.96379(17) 0.56693(8) 0.0334(4) Uani 1 1 d . . . . . H20 H 0.282692 1.021295 0.602151 0.040 Uiso 1 1 calc R U . . . C21 C 0.37074(19) 0.98233(16) 0.51885(9) 0.0310(4) Uani 1 1 d . . . . . H21 H 0.433095 1.053985 0.520503 0.037 Uiso 1 1 calc R U . . . C22 C 0.37031(16) 0.89638(15) 0.46806(8) 0.0249(3) Uani 1 1 d . . . . . H22 H 0.431539 0.910611 0.434770 0.030 Uiso 1 1 calc R U . . . 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 0.02087(9) 0.01567(7) 0.01825(8) 0.00096(6) 0.00328(8) 0.00100(7) Cl1 0.0337(2) 0.02302(15) 0.02429(17) 0.00181(13) 0.01000(16) -0.00030(14) O1 0.0420(8) 0.0212(5) 0.0307(6) -0.0009(5) -0.0043(5) 0.0098(5) O2 0.0337(7) 0.0356(6) 0.0299(6) 0.0039(5) 0.0140(5) 0.0067(5) N1 0.0235(6) 0.0175(5) 0.0214(6) -0.0017(5) 0.0015(5) 0.0018(4) N2 0.0232(6) 0.0200(6) 0.0191(6) 0.0021(4) 0.0034(5) 0.0027(5) N3 0.0253(6) 0.0190(5) 0.0217(6) 0.0019(5) 0.0024(6) 0.0025(4) C1 0.0257(8) 0.0185(6) 0.0242(7) -0.0034(5) 0.0032(6) 0.0017(5) C2 0.0433(11) 0.0282(8) 0.0312(9) -0.0078(7) -0.0041(8) 0.0133(8) C3 0.0233(8) 0.0192(6) 0.0279(8) -0.0002(5) -0.0001(6) 0.0033(6) C4 0.0269(8) 0.0218(7) 0.0233(7) 0.0028(5) -0.0011(6) 0.0007(6) C5 0.0358(9) 0.0300(8) 0.0294(9) 0.0070(7) -0.0027(7) 0.0064(7) C6 0.0448(12) 0.0415(10) 0.0272(9) 0.0111(7) -0.0056(8) 0.0049(9) C7 0.0436(11) 0.0439(10) 0.0214(8) 0.0038(7) 0.0000(7) 0.0017(8) C8 0.0341(10) 0.0311(7) 0.0222(7) 0.0011(6) 0.0029(7) 0.0008(7) C9 0.0237(7) 0.0214(6) 0.0217(6) 0.0023(5) 0.0017(7) -0.0008(6) C10 0.0241(8) 0.0220(6) 0.0241(7) -0.0003(6) 0.0044(6) 0.0005(6) C11 0.0263(8) 0.0264(7) 0.0282(8) 0.0042(6) 0.0059(6) 0.0068(6) C12 0.0352(9) 0.0175(6) 0.0322(8) 0.0003(5) 0.0044(7) 0.0000(6) C13 0.0451(11) 0.0295(8) 0.0357(9) -0.0073(7) -0.0037(8) -0.0066(7) C14 0.0333(9) 0.0273(8) 0.0277(8) 0.0068(6) -0.0012(7) 0.0074(7) C15 0.0387(11) 0.0463(11) 0.0376(10) -0.0005(9) -0.0088(9) 0.0000(9) C16 0.0242(7) 0.0221(6) 0.0237(7) -0.0018(6) 0.0048(6) -0.0019(5) C17 0.0247(8) 0.0193(6) 0.0227(7) 0.0015(5) -0.0011(6) -0.0006(5) C18 0.0372(10) 0.0280(8) 0.0284(8) -0.0037(6) 0.0071(7) -0.0085(7) C19 0.0453(11) 0.0370(9) 0.0274(8) -0.0058(7) 0.0083(8) -0.0014(8) C20 0.0434(12) 0.0283(7) 0.0285(8) -0.0063(6) -0.0078(7) 0.0049(7) C21 0.0332(9) 0.0231(7) 0.0367(9) -0.0026(6) -0.0104(7) -0.0024(6) C22 0.0230(7) 0.0235(7) 0.0284(8) 0.0026(6) -0.0020(6) -0.0011(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 N1 91.69(5) . . ? N2 Ni1 N3 85.96(5) . . ? N1 Ni1 N3 172.85(6) . . ? N2 Ni1 Cl1 171.32(4) . . ? N1 Ni1 Cl1 91.73(4) . . ? N3 Ni1 Cl1 91.55(4) . . ? C3 O1 C2 106.20(13) . . ? C3 N1 C1 107.70(11) . . ? C3 N1 Ni1 126.58(10) . . ? C1 N1 Ni1 124.64(10) . . ? C10 N2 C9 119.11(13) . . ? C10 N2 Ni1 115.07(10) . . ? C9 N2 Ni1 125.74(11) . . ? C11 N3 C14 108.05(13) . . ? C11 N3 C12 110.45(13) . . ? C14 N3 C12 105.85(12) . . ? C11 N3 Ni1 106.44(9) . . ? C14 N3 Ni1 116.01(10) . . ? C12 N3 Ni1 110.02(10) . . ? N1 C1 C16 108.30(13) . . ? N1 C1 C2 102.02(13) . . ? C16 C1 C2 114.04(14) . . ? N1 C1 H1 110.7 . . ? C16 C1 H1 110.7 . . ? C2 C1 H1 110.7 . . ? O1 C2 C1 104.43(13) . . ? O1 C2 H2A 110.9 . . ? C1 C2 H2A 110.9 . . ? O1 C2 H2AB 110.9 . . ? C1 C2 H2AB 110.9 . . ? H2A C2 H2AB 108.9 . . ? N1 C3 O1 116.56(14) . . ? N1 C3 C4 127.03(13) . . ? O1 C3 C4 116.40(13) . . ? C5 C4 C9 120.55(15) . . ? C5 C4 C3 119.03(15) . . ? C9 C4 C3 120.41(14) . . ? C6 C5 C4 120.82(17) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 118.83(16) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 121.34(17) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 121.07(16) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C8 C9 C4 117.35(14) . . ? C8 C9 N2 121.96(14) . . ? C4 C9 N2 120.63(13) . . ? O2 C10 N2 128.00(15) . . ? O2 C10 C11 118.85(15) . . ? N2 C10 C11 113.12(14) . . ? N3 C11 C10 112.33(13) . . ? N3 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? N3 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? N3 C12 C13 115.16(13) . . ? N3 C12 H12A 108.5 . . ? C13 C12 H12A 108.5 . . ? N3 C12 H12B 108.5 . . ? C13 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 114.59(14) . . ? N3 C14 H14A 108.6 . . ? C15 C14 H14A 108.6 . . ? N3 C14 H14B 108.6 . . ? C15 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C1 113.98(13) . . ? C17 C16 H16A 108.8 . . ? C1 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? C1 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C22 118.57(14) . . ? C18 C17 C16 122.13(14) . . ? C22 C17 C16 119.30(14) . . ? C17 C18 C19 120.99(16) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 119.47(17) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C21 C20 C19 120.12(16) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 120.06(16) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C17 C22 C21 120.71(15) . . ? C17 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? 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 1.8826(12) . ? Ni1 N1 1.8904(12) . ? Ni1 N3 1.9611(12) . ? Ni1 Cl1 2.1896(4) . ? O1 C3 1.3505(18) . ? O1 C2 1.455(2) . ? O2 C10 1.2306(19) . ? N1 C3 1.2862(19) . ? N1 C1 1.4953(19) . ? N2 C10 1.356(2) . ? N2 C9 1.4114(19) . ? N3 C11 1.486(2) . ? N3 C14 1.506(2) . ? N3 C12 1.509(2) . ? C1 C16 1.522(2) . ? C1 C2 1.527(2) . ? C1 H1 1.0000 . ? C2 H2A 0.9900 . ? C2 H2AB 0.9900 . ? C3 C4 1.446(2) . ? C4 C5 1.402(2) . ? C4 C9 1.408(2) . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C6 C7 1.384(3) . ? C6 H6 0.9500 . ? C7 C8 1.380(2) . ? C7 H7 0.9500 . ? C8 C9 1.405(2) . ? C8 H8 0.9500 . ? C10 C11 1.509(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.513(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.515(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.514(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.387(2) . ? C17 C22 1.388(2) . ? C18 C19 1.394(2) . ? C18 H18 0.9500 . ? C19 C20 1.382(3) . ? C19 H19 0.9500 . ? C20 C21 1.379(3) . ? C20 H20 0.9500 . ? C21 C22 1.388(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 C3 12.98(14) . . . . ? Cl1 Ni1 N1 C3 -159.04(14) . . . . ? N2 Ni1 N1 C1 -153.65(12) . . . . ? Cl1 Ni1 N1 C1 34.34(12) . . . . ? N1 Ni1 N2 C10 153.65(12) . . . . ? N3 Ni1 N2 C10 -19.58(12) . . . . ? N1 Ni1 N2 C9 -29.69(13) . . . . ? N3 Ni1 N2 C9 157.07(13) . . . . ? C3 N1 C1 C16 -106.75(15) . . . . ? Ni1 N1 C1 C16 62.01(15) . . . . ? C3 N1 C1 C2 13.86(17) . . . . ? Ni1 N1 C1 C2 -177.39(12) . . . . ? C3 O1 C2 C1 15.0(2) . . . . ? N1 C1 C2 O1 -17.14(18) . . . . ? C16 C1 C2 O1 99.38(16) . . . . ? C1 N1 C3 O1 -5.07(19) . . . . ? Ni1 N1 C3 O1 -173.55(11) . . . . ? C1 N1 C3 C4 175.61(17) . . . . ? Ni1 N1 C3 C4 7.1(3) . . . . ? C2 O1 C3 N1 -6.8(2) . . . . ? C2 O1 C3 C4 172.62(16) . . . . ? N1 C3 C4 C5 161.32(18) . . . . ? O1 C3 C4 C5 -18.0(2) . . . . ? N1 C3 C4 C9 -17.5(3) . . . . ? O1 C3 C4 C9 163.20(15) . . . . ? C9 C4 C5 C6 1.1(3) . . . . ? C3 C4 C5 C6 -177.69(18) . . . . ? C4 C5 C6 C7 0.7(3) . . . . ? C5 C6 C7 C8 -1.4(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 C4 1.5(3) . . . . ? C7 C8 C9 N2 178.76(17) . . . . ? C5 C4 C9 C8 -2.2(2) . . . . ? C3 C4 C9 C8 176.60(16) . . . . ? C5 C4 C9 N2 -179.45(16) . . . . ? C3 C4 C9 N2 -0.7(2) . . . . ? C10 N2 C9 C8 26.8(2) . . . . ? Ni1 N2 C9 C8 -149.69(14) . . . . ? C10 N2 C9 C4 -156.03(15) . . . . ? Ni1 N2 C9 C4 27.4(2) . . . . ? C9 N2 C10 O2 14.3(3) . . . . ? Ni1 N2 C10 O2 -168.77(15) . . . . ? C9 N2 C10 C11 -167.65(14) . . . . ? Ni1 N2 C10 C11 9.24(18) . . . . ? C14 N3 C11 C10 -149.88(13) . . . . ? C12 N3 C11 C10 94.77(16) . . . . ? Ni1 N3 C11 C10 -24.63(16) . . . . ? O2 C10 C11 N3 -170.54(15) . . . . ? N2 C10 C11 N3 11.3(2) . . . . ? C11 N3 C12 C13 -57.84(19) . . . . ? C14 N3 C12 C13 -174.56(15) . . . . ? Ni1 N3 C12 C13 59.38(17) . . . . ? C11 N3 C14 C15 69.60(18) . . . . ? C12 N3 C14 C15 -172.06(16) . . . . ? Ni1 N3 C14 C15 -49.75(19) . . . . ? N1 C1 C16 C17 174.16(12) . . . . ? C2 C1 C16 C17 61.35(18) . . . . ? C1 C16 C17 C18 48.5(2) . . . . ? C1 C16 C17 C22 -132.29(15) . . . . ? C22 C17 C18 C19 -2.0(3) . . . . ? C16 C17 C18 C19 177.22(17) . . . . ? C17 C18 C19 C20 -0.7(3) . . . . ? C18 C19 C20 C21 2.5(3) . . . . ? C19 C20 C21 C22 -1.6(3) . . . . ? C18 C17 C22 C21 2.8(2) . . . . ? C16 C17 C22 C21 -176.36(15) . . . . ? C20 C21 C22 C17 -1.1(3) . . . . ?