#------------------------------------------------------------------------------ #$Date: 2021-09-06 15:01:16 +0300 (Mon, 06 Sep 2021) $ #$Revision: 268858 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/07/7060708.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_7060708 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 'C19 H28 Cl N3 Ni O2' _chemical_formula_sum 'C19 H28 Cl N3 Ni O2' _chemical_formula_weight 424.60 _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 9.7315(3) _cell_length_b 9.8437(3) _cell_length_c 21.1840(7) _cell_measurement_reflns_used 9376 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.49 _cell_measurement_theta_min 2.30 _cell_volume 2029.30(11) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0240 _diffrn_reflns_av_unetI/netI 0.0249 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 36549 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.523 _diffrn_reflns_theta_min 2.281 _diffrn_source 'micro-focus sealed tube' _diffrn_source_type 'Incoatech I\mS HB' _exptl_absorpt_coefficient_mu 1.105 _exptl_absorpt_correction_T_max 0.947 _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 1.390 _exptl_crystal_description plate _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.305 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.023(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 6183 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0193 _refine_ls_R_factor_gt 0.0187 _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^)+(0.0206P)^2^+0.3822P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.0483 _reflns_Friedel_coverage 0.773 _reflns_Friedel_fraction_full 0.996 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 6036 _reflns_number_total 6183 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01698a2.cif _cod_data_source_block RJ-E-04 _cod_depositor_comments 'Adding full bibliography for 7060706--7060708.cif.' _cod_database_code 7060708 _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 0.947 _shelx_res_file ; TITL mo_RJ_E_04_0m_a.res in P2(1)2(1)2(1) mo_RJ_E_04_0m_a.res created by SHELXL-2018/3 at 23:23:47 on 29-Mar-2021 CELL 0.71073 9.7315 9.8437 21.1840 90.000 90.000 90.000 ZERR 4.000 0.0003 0.0003 0.0007 0.000 0.000 0.000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N O Cl Ni UNIT 76 112 12 8 4 4 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TWIN SIZE 0.20 0.17 0.05 CONF L.S. 30 OMIT 1 0 1 EADP C19A C19B ACTA BOND $H FMAP 2 PLAN 20 TEMP -173.160 WGHT 0.020600 0.382200 BASF 0.02309 FVAR 0.49258 0.34774 NI1 6 0.222472 0.504466 0.415953 11.00000 0.01431 0.01368 = 0.01286 -0.00078 0.00021 0.00063 CL1 5 0.177186 0.394891 0.328127 11.00000 0.02041 0.02208 = 0.01418 -0.00252 -0.00082 -0.00054 O1 4 0.590477 0.343523 0.466427 11.00000 0.01803 0.02377 = 0.01975 -0.00012 0.00036 0.00585 O2 4 0.166567 0.770653 0.553197 11.00000 0.02802 0.02203 = 0.02970 -0.01211 0.00033 0.00208 N1 3 0.396789 0.421145 0.422062 11.00000 0.01532 0.01597 = 0.01543 -0.00268 0.00268 0.00015 N2 3 0.237329 0.578367 0.497806 11.00000 0.01639 0.01531 = 0.01474 -0.00257 0.00020 0.00060 N3 3 0.053062 0.610478 0.408875 11.00000 0.02061 0.01794 = 0.01786 0.00101 -0.00230 0.00413 C1 1 0.485460 0.381503 0.367820 11.00000 0.01676 0.01816 = 0.01586 -0.00241 0.00343 0.00070 AFIX 13 H1 2 0.433630 0.321279 0.338184 11.00000 -1.20000 AFIX 0 C2 1 0.599693 0.301315 0.400905 11.00000 0.02325 0.02485 = 0.02086 0.00004 0.00490 0.00786 AFIX 23 H2A 2 0.584335 0.202295 0.396771 11.00000 -1.20000 H2AB 2 0.690768 0.324133 0.382984 11.00000 -1.20000 AFIX 0 C3 1 0.465772 0.401971 0.473290 11.00000 0.01580 0.01453 = 0.01844 -0.00133 0.00083 0.00024 C4 1 0.422740 0.433195 0.537035 11.00000 0.01822 0.01697 = 0.01543 -0.00202 -0.00120 -0.00159 C5 1 0.495003 0.373509 0.587278 11.00000 0.02275 0.02350 = 0.02006 -0.00135 -0.00409 0.00136 AFIX 43 H5 2 0.571433 0.316395 0.578677 11.00000 -1.20000 AFIX 0 C6 1 0.456272 0.396867 0.648976 11.00000 0.03099 0.03020 = 0.01702 -0.00010 -0.00773 -0.00200 AFIX 43 H6 2 0.505546 0.356562 0.682857 11.00000 -1.20000 AFIX 0 C7 1 0.343673 0.480566 0.660775 11.00000 0.03127 0.02916 = 0.01484 -0.00365 -0.00155 -0.00425 AFIX 43 H7 2 0.315527 0.496273 0.703091 11.00000 -1.20000 AFIX 0 C8 1 0.272059 0.541290 0.611707 11.00000 0.02205 0.02234 = 0.01744 -0.00485 0.00093 -0.00388 AFIX 43 H8 2 0.195862 0.598224 0.620977 11.00000 -1.20000 AFIX 0 C9 1 0.310418 0.519960 0.548328 11.00000 0.01696 0.01540 = 0.01612 -0.00305 -0.00031 -0.00294 C10 1 0.161406 0.693173 0.507856 11.00000 0.01856 0.01684 = 0.02255 -0.00279 0.00279 -0.00093 C11 1 0.063811 0.724481 0.454578 11.00000 0.02585 0.01702 = 0.02366 -0.00248 -0.00036 0.00632 AFIX 23 H11A 2 -0.028332 0.743989 0.472188 11.00000 -1.20000 H11B 2 0.095839 0.806856 0.432165 11.00000 -1.20000 AFIX 0 C12 1 -0.068691 0.522648 0.424618 11.00000 0.01417 0.02723 = 0.02951 -0.00376 -0.00299 0.00250 AFIX 23 H12A 2 -0.073156 0.447296 0.393734 11.00000 -1.20000 H12B 2 -0.153321 0.577433 0.419669 11.00000 -1.20000 AFIX 0 C13 1 -0.066871 0.462791 0.490658 11.00000 0.01916 0.03181 = 0.03029 0.00174 0.00456 -0.00340 AFIX 137 H13A 2 -0.149826 0.408116 0.497173 11.00000 -1.50000 H13B 2 -0.064177 0.536399 0.521781 11.00000 -1.50000 H13C 2 0.014563 0.405218 0.495650 11.00000 -1.50000 AFIX 0 C14 1 0.025461 0.670021 0.344439 11.00000 0.03985 0.02508 = 0.02230 0.00499 -0.00570 0.01106 AFIX 23 H14A 2 -0.000884 0.595445 0.315514 11.00000 -1.20000 H14B 2 -0.053946 0.732504 0.347657 11.00000 -1.20000 AFIX 0 C15 1 0.144337 0.746203 0.315710 11.00000 0.06867 0.02665 = 0.02927 0.00944 0.00780 0.00378 AFIX 137 H15A 2 0.116173 0.784922 0.275102 11.00000 -1.50000 H15B 2 0.221470 0.683780 0.309136 11.00000 -1.50000 H15C 2 0.172674 0.819450 0.344210 11.00000 -1.50000 AFIX 0 C16 1 0.537661 0.507137 0.333262 11.00000 0.01787 0.01865 = 0.01907 -0.00026 0.00078 -0.00155 AFIX 23 H16A 2 0.600409 0.558017 0.361442 11.00000 -1.20000 H16B 2 0.458792 0.566933 0.323299 11.00000 -1.20000 AFIX 0 C17 1 0.613887 0.472174 0.271774 11.00000 0.02596 0.02354 = 0.02210 0.00267 0.00679 -0.00080 AFIX 13 H17 2 0.686316 0.409055 0.287930 11.00000 -1.20000 AFIX 0 C18 1 0.699881 0.588366 0.249467 11.00000 0.06100 0.05556 = 0.03470 0.00260 0.01428 -0.03170 AFIX 137 H18A 2 0.740688 0.565770 0.208498 11.00000 -1.50000 H18B 2 0.773077 0.606054 0.280159 11.00000 -1.50000 H18C 2 0.642291 0.669496 0.245113 11.00000 -1.50000 AFIX 0 PART 1 C19A 1 0.545968 0.387765 0.228083 21.00000 0.02981 0.05610 = 0.01864 -0.00344 0.00056 -0.01217 AFIX 137 H19A 2 0.453400 0.423135 0.220228 21.00000 -1.50000 H19B 2 0.539528 0.295506 0.245215 21.00000 -1.50000 H19C 2 0.597720 0.385923 0.188407 21.00000 -1.50000 AFIX 0 PART 2 C19B 1 0.503280 0.451580 0.217201 -21.00000 0.02981 0.05610 = 0.01864 -0.00344 0.00056 -0.01217 AFIX 137 H19D 2 0.458715 0.538598 0.207929 -21.00000 -1.50000 H19E 2 0.433968 0.385716 0.230971 -21.00000 -1.50000 H19F 2 0.549093 0.417752 0.179120 -21.00000 -1.50000 PART 0 AFIX 0 HKLF 4 REM mo_RJ_E_04_0m_a.res in P2(1)2(1)2(1) REM wR2 = 0.048283, GooF = S = 1.03042, Restrained GooF = 1.03042 for all data REM R1 = 0.018720 for 6036 Fo > 4sig(Fo) and 0.019342 for all 6183 data REM 245 parameters refined using 0 restraints END WGHT 0.0206 0.3822 REM Highest difference peak 0.305, deepest hole -0.295, 1-sigma level 0.042 Q1 1 0.2880 0.5137 0.5807 11.00000 0.05 0.30 Q2 1 0.4485 0.4198 0.5073 11.00000 0.05 0.30 Q3 1 0.4815 0.4000 0.6164 11.00000 0.05 0.27 Q4 1 0.4602 0.4027 0.5608 11.00000 0.05 0.26 Q5 1 0.3752 0.4836 0.5434 11.00000 0.05 0.24 Q6 1 0.1130 0.7109 0.4801 11.00000 0.05 0.24 Q7 1 -0.0717 0.5025 0.4582 11.00000 0.05 0.22 Q8 1 0.3125 0.5088 0.6330 11.00000 0.05 0.21 Q9 1 0.6278 0.5956 0.2411 11.00000 0.05 0.21 Q10 1 0.5713 0.4968 0.3033 11.00000 0.05 0.21 Q11 1 0.2794 0.5581 0.5205 11.00000 0.05 0.20 Q12 1 0.2782 0.5016 0.3878 11.00000 0.05 0.20 Q13 1 0.1628 0.5062 0.3893 11.00000 0.05 0.20 Q14 1 0.5455 0.3378 0.3823 11.00000 0.05 0.19 Q15 1 0.2414 0.5603 0.4646 11.00000 0.05 0.19 Q16 1 0.4348 0.4319 0.4486 11.00000 0.05 0.19 Q17 1 0.0792 0.7244 0.3218 11.00000 0.05 0.19 Q18 1 0.6488 0.3854 0.2697 11.00000 0.05 0.17 Q19 1 -0.0012 0.5742 0.4181 11.00000 0.05 0.17 Q20 1 0.4200 0.4637 0.6531 11.00000 0.05 0.17 ; _shelx_res_checksum 12225 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 0.22247(2) 0.50447(2) 0.41595(2) 0.01362(4) Uani 1 1 d . . . . . Cl1 Cl 0.17719(4) 0.39489(4) 0.32813(2) 0.01889(7) Uani 1 1 d . . . . . O1 O 0.59048(12) 0.34352(12) 0.46643(5) 0.0205(2) Uani 1 1 d . . . . . O2 O 0.16657(14) 0.77065(12) 0.55320(6) 0.0266(3) Uani 1 1 d . . . . . N1 N 0.39679(12) 0.42115(12) 0.42206(6) 0.0156(2) Uani 1 1 d . . . . . N2 N 0.23733(13) 0.57837(12) 0.49781(6) 0.0155(2) Uani 1 1 d . . . . . N3 N 0.05306(13) 0.61048(13) 0.40888(6) 0.0188(2) Uani 1 1 d . . . . . C1 C 0.48546(15) 0.38150(16) 0.36782(7) 0.0169(3) Uani 1 1 d . . . . . H1 H 0.433630 0.321279 0.338184 0.020 Uiso 1 1 calc R U . . . C2 C 0.59969(17) 0.30132(17) 0.40091(8) 0.0230(3) Uani 1 1 d . . . . . H2A H 0.584335 0.202295 0.396771 0.028 Uiso 1 1 calc R U . . . H2AB H 0.690768 0.324133 0.382984 0.028 Uiso 1 1 calc R U . . . C3 C 0.46577(15) 0.40197(15) 0.47329(7) 0.0163(3) Uani 1 1 d . . . . . C4 C 0.42274(16) 0.43320(15) 0.53703(7) 0.0169(3) Uani 1 1 d . . . . . C5 C 0.49500(16) 0.37351(16) 0.58728(8) 0.0221(3) Uani 1 1 d . . . . . H5 H 0.571433 0.316395 0.578677 0.027 Uiso 1 1 calc R U . . . C6 C 0.45627(19) 0.39687(19) 0.64898(8) 0.0261(3) Uani 1 1 d . . . . . H6 H 0.505546 0.356562 0.682857 0.031 Uiso 1 1 calc R U . . . C7 C 0.34367(18) 0.48057(18) 0.66078(7) 0.0251(3) Uani 1 1 d . . . . . H7 H 0.315527 0.496273 0.703091 0.030 Uiso 1 1 calc R U . . . C8 C 0.27206(18) 0.54129(16) 0.61171(7) 0.0206(3) Uani 1 1 d . . . . . H8 H 0.195862 0.598224 0.620977 0.025 Uiso 1 1 calc R U . . . C9 C 0.31042(14) 0.51996(15) 0.54833(7) 0.0162(3) Uani 1 1 d . . . . . C10 C 0.16141(16) 0.69317(15) 0.50786(8) 0.0193(3) Uani 1 1 d . . . . . C11 C 0.06381(18) 0.72448(16) 0.45458(8) 0.0222(3) Uani 1 1 d . . . . . H11A H -0.028332 0.743989 0.472188 0.027 Uiso 1 1 calc R U . . . H11B H 0.095839 0.806856 0.432165 0.027 Uiso 1 1 calc R U . . . C12 C -0.06869(15) 0.52265(17) 0.42462(8) 0.0236(3) Uani 1 1 d . . . . . H12A H -0.073156 0.447296 0.393734 0.028 Uiso 1 1 calc R U . . . H12B H -0.153321 0.577433 0.419669 0.028 Uiso 1 1 calc R U . . . C13 C -0.06687(18) 0.46279(18) 0.49066(9) 0.0271(4) Uani 1 1 d . . . . . H13A H -0.149826 0.408116 0.497173 0.041 Uiso 1 1 calc R U . . . H13B H -0.064177 0.536399 0.521781 0.041 Uiso 1 1 calc R U . . . H13C H 0.014563 0.405218 0.495650 0.041 Uiso 1 1 calc R U . . . C14 C 0.0255(2) 0.67002(19) 0.34444(9) 0.0291(4) Uani 1 1 d . . . . . H14A H -0.000884 0.595445 0.315514 0.035 Uiso 1 1 calc R U . . . H14B H -0.053946 0.732504 0.347657 0.035 Uiso 1 1 calc R U . . . C15 C 0.1443(3) 0.7462(2) 0.31571(10) 0.0415(5) Uani 1 1 d . . . . . H15A H 0.116173 0.784922 0.275102 0.062 Uiso 1 1 calc R U . . . H15B H 0.221470 0.683780 0.309136 0.062 Uiso 1 1 calc R U . . . H15C H 0.172674 0.819450 0.344210 0.062 Uiso 1 1 calc R U . . . C16 C 0.53766(14) 0.50714(17) 0.33326(7) 0.0185(2) Uani 1 1 d . . . . . H16A H 0.600409 0.558017 0.361442 0.022 Uiso 1 1 calc R U . . . H16B H 0.458792 0.566933 0.323299 0.022 Uiso 1 1 calc R U . . . C17 C 0.61389(18) 0.47217(17) 0.27177(8) 0.0239(3) Uani 1 1 d . . . . . H17 H 0.686316 0.409055 0.287930 0.029 Uiso 1 1 calc R U . A 1 C18 C 0.6999(3) 0.5884(3) 0.24947(11) 0.0504(6) Uani 1 1 d . . . . . H18A H 0.740688 0.565770 0.208498 0.076 Uiso 1 1 calc R U . . . H18B H 0.773077 0.606054 0.280159 0.076 Uiso 1 1 calc R U . . . H18C H 0.642291 0.669496 0.245113 0.076 Uiso 1 1 calc R U . . . C19A C 0.5460(7) 0.3878(8) 0.2281(3) 0.0348(7) Uani 0.348(5) 1 d . . P B 1 H19A H 0.453400 0.423135 0.220228 0.052 Uiso 0.348(5) 1 calc R U P B 1 H19B H 0.539528 0.295506 0.245215 0.052 Uiso 0.348(5) 1 calc R U P B 1 H19C H 0.597720 0.385923 0.188407 0.052 Uiso 0.348(5) 1 calc R U P B 1 C19B C 0.5033(4) 0.4516(4) 0.21720(15) 0.0348(7) Uani 0.652(5) 1 d . . P B 2 H19D H 0.458715 0.538598 0.207929 0.052 Uiso 0.652(5) 1 calc R U P B 2 H19E H 0.433968 0.385716 0.230971 0.052 Uiso 0.652(5) 1 calc R U P B 2 H19F H 0.549093 0.417752 0.179120 0.052 Uiso 0.652(5) 1 calc R U P B 2 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 0.01431(8) 0.01368(8) 0.01286(8) -0.00078(7) 0.00021(6) 0.00063(7) Cl1 0.02041(15) 0.02208(16) 0.01418(14) -0.00252(12) -0.00082(12) -0.00054(13) O1 0.0180(5) 0.0238(5) 0.0198(5) -0.0001(4) 0.0004(4) 0.0059(4) O2 0.0280(6) 0.0220(5) 0.0297(6) -0.0121(5) 0.0003(5) 0.0021(5) N1 0.0153(5) 0.0160(5) 0.0154(5) -0.0027(5) 0.0027(4) 0.0002(4) N2 0.0164(5) 0.0153(5) 0.0147(5) -0.0026(4) 0.0002(4) 0.0006(4) N3 0.0206(6) 0.0179(5) 0.0179(6) 0.0010(5) -0.0023(5) 0.0041(5) C1 0.0168(6) 0.0182(7) 0.0159(6) -0.0024(5) 0.0034(5) 0.0007(5) C2 0.0233(8) 0.0249(8) 0.0209(8) 0.0000(6) 0.0049(6) 0.0079(6) C3 0.0158(6) 0.0145(6) 0.0184(6) -0.0013(5) 0.0008(5) 0.0002(5) C4 0.0182(6) 0.0170(6) 0.0154(7) -0.0020(5) -0.0012(5) -0.0016(5) C5 0.0228(7) 0.0235(7) 0.0201(7) -0.0014(6) -0.0041(6) 0.0014(6) C6 0.0310(8) 0.0302(8) 0.0170(7) -0.0001(7) -0.0077(6) -0.0020(7) C7 0.0313(8) 0.0292(8) 0.0148(6) -0.0036(6) -0.0016(5) -0.0042(7) C8 0.0221(7) 0.0223(7) 0.0174(7) -0.0049(5) 0.0009(6) -0.0039(6) C9 0.0170(6) 0.0154(6) 0.0161(6) -0.0031(5) -0.0003(5) -0.0029(5) C10 0.0186(7) 0.0168(6) 0.0225(7) -0.0028(5) 0.0028(6) -0.0009(5) C11 0.0259(8) 0.0170(6) 0.0237(8) -0.0025(6) -0.0004(6) 0.0063(6) C12 0.0142(6) 0.0272(8) 0.0295(8) -0.0038(6) -0.0030(5) 0.0025(5) C13 0.0192(7) 0.0318(9) 0.0303(9) 0.0017(7) 0.0046(6) -0.0034(6) C14 0.0399(10) 0.0251(8) 0.0223(8) 0.0050(6) -0.0057(7) 0.0111(7) C15 0.0687(16) 0.0266(9) 0.0293(10) 0.0094(8) 0.0078(10) 0.0038(10) C16 0.0179(6) 0.0187(6) 0.0191(6) -0.0003(6) 0.0008(5) -0.0015(6) C17 0.0260(7) 0.0235(8) 0.0221(7) 0.0027(6) 0.0068(6) -0.0008(6) C18 0.0610(15) 0.0556(14) 0.0347(11) 0.0026(10) 0.0143(10) -0.0317(13) C19A 0.0298(16) 0.056(2) 0.0186(12) -0.0034(13) 0.0006(10) -0.0122(13) C19B 0.0298(16) 0.056(2) 0.0186(12) -0.0034(13) 0.0006(10) -0.0122(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 92.04(5) . . ? N2 Ni1 N3 85.95(5) . . ? N1 Ni1 N3 173.47(6) . . ? N2 Ni1 Cl1 169.78(4) . . ? N1 Ni1 Cl1 91.43(4) . . ? N3 Ni1 Cl1 91.60(4) . . ? C3 O1 C2 106.28(12) . . ? C3 N1 C1 108.02(12) . . ? C3 N1 Ni1 126.06(10) . . ? C1 N1 Ni1 125.55(10) . . ? C10 N2 C9 119.49(13) . . ? C10 N2 Ni1 114.88(10) . . ? C9 N2 Ni1 125.46(9) . . ? C11 N3 C12 110.19(13) . . ? C11 N3 C14 107.97(13) . . ? C12 N3 C14 106.47(13) . . ? C11 N3 Ni1 107.07(10) . . ? C12 N3 Ni1 109.88(9) . . ? C14 N3 Ni1 115.23(11) . . ? N1 C1 C16 110.56(12) . . ? N1 C1 C2 101.68(12) . . ? C16 C1 C2 113.31(13) . . ? N1 C1 H1 110.3 . . ? C16 C1 H1 110.3 . . ? C2 C1 H1 110.3 . . ? O1 C2 C1 104.18(12) . . ? 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 116.06(13) . . ? N1 C3 C4 127.12(13) . . ? O1 C3 C4 116.80(13) . . ? C5 C4 C9 120.92(14) . . ? C5 C4 C3 118.26(14) . . ? C9 C4 C3 120.82(13) . . ? C6 C5 C4 120.76(15) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 118.90(15) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 121.03(15) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 121.11(15) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C4 C9 N2 120.72(13) . . ? C4 C9 C8 117.26(13) . . ? N2 C9 C8 121.98(13) . . ? O2 C10 N2 127.84(16) . . ? O2 C10 C11 119.00(14) . . ? N2 C10 C11 113.15(13) . . ? N3 C11 C10 112.21(12) . . ? N3 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? N3 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N3 C12 C13 114.72(13) . . ? N3 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? N3 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? 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 . . ? C15 C14 N3 114.95(17) . . ? C15 C14 H14A 108.5 . . ? N3 C14 H14A 108.5 . . ? C15 C14 H14B 108.5 . . ? N3 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? 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 . . ? C1 C16 C17 112.70(13) . . ? C1 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? C1 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C19A C17 C18 120.4(3) . . ? C19A C17 C16 117.5(3) . . ? C18 C17 C16 111.52(16) . . ? C18 C17 C19B 104.3(2) . . ? C16 C17 C19B 108.50(17) . . ? C19A C17 H17 100.9 . . ? C18 C17 H17 100.9 . . ? C16 C17 H17 100.9 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19A H19A 109.5 . . ? C17 C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? C17 C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? C17 C19B H19D 109.5 . . ? C17 C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C17 C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? 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 1.8859(12) . ? Ni1 N1 1.8887(12) . ? Ni1 N3 1.9569(13) . ? Ni1 Cl1 2.1952(4) . ? O1 C3 1.3509(18) . ? O1 C2 1.452(2) . ? O2 C10 1.2275(19) . ? N1 C3 1.2900(19) . ? N1 C1 1.4890(18) . ? N2 C10 1.3669(19) . ? N2 C9 1.4078(18) . ? N3 C11 1.486(2) . ? N3 C12 1.504(2) . ? N3 C14 1.510(2) . ? C1 C16 1.524(2) . ? C1 C2 1.533(2) . ? C1 H1 1.0000 . ? C2 H2A 0.9900 . ? C2 H2AB 0.9900 . ? C3 C4 1.447(2) . ? C4 C5 1.404(2) . ? C4 C9 1.408(2) . ? C5 C6 1.380(2) . ? C5 H5 0.9500 . ? C6 C7 1.394(3) . ? C6 H6 0.9500 . ? C7 C8 1.387(2) . ? C7 H7 0.9500 . ? C8 C9 1.409(2) . ? C8 H8 0.9500 . ? C10 C11 1.507(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.518(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.507(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.538(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C19A 1.409(6) . ? C17 C18 1.494(3) . ? C17 C19B 1.593(4) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19A H19A 0.9800 . ? C19A H19B 0.9800 . ? C19A H19C 0.9800 . ? C19B H19D 0.9800 . ? C19B H19E 0.9800 . ? C19B H19F 0.9800 . ? 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 15.65(13) . . . . ? Cl1 Ni1 N1 C3 -154.74(12) . . . . ? N2 Ni1 N1 C1 -156.46(12) . . . . ? Cl1 Ni1 N1 C1 33.15(11) . . . . ? N1 Ni1 N2 C10 154.58(11) . . . . ? N3 Ni1 N2 C10 -19.20(11) . . . . ? Cl1 Ni1 N2 C10 -95.6(2) . . . . ? N1 Ni1 N2 C9 -30.14(12) . . . . ? N3 Ni1 N2 C9 156.08(12) . . . . ? Cl1 Ni1 N2 C9 79.7(3) . . . . ? C3 N1 C1 C16 -105.69(14) . . . . ? Ni1 N1 C1 C16 67.62(15) . . . . ? C3 N1 C1 C2 14.91(15) . . . . ? Ni1 N1 C1 C2 -171.78(10) . . . . ? C3 O1 C2 C1 16.96(16) . . . . ? N1 C1 C2 O1 -18.91(15) . . . . ? C16 C1 C2 O1 99.74(14) . . . . ? C1 N1 C3 O1 -4.94(18) . . . . ? Ni1 N1 C3 O1 -178.21(10) . . . . ? C1 N1 C3 C4 176.66(14) . . . . ? Ni1 N1 C3 C4 3.4(2) . . . . ? C2 O1 C3 N1 -8.20(18) . . . . ? C2 O1 C3 C4 170.37(13) . . . . ? N1 C3 C4 C5 163.55(15) . . . . ? O1 C3 C4 C5 -14.8(2) . . . . ? N1 C3 C4 C9 -15.8(2) . . . . ? O1 C3 C4 C9 165.85(13) . . . . ? C9 C4 C5 C6 1.0(2) . . . . ? C3 C4 C5 C6 -178.31(15) . . . . ? C4 C5 C6 C7 0.2(3) . . . . ? C5 C6 C7 C8 -0.8(3) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C5 C4 C9 N2 -179.29(14) . . . . ? C3 C4 C9 N2 0.0(2) . . . . ? C5 C4 C9 C8 -1.5(2) . . . . ? C3 C4 C9 C8 177.78(14) . . . . ? C10 N2 C9 C4 -158.53(14) . . . . ? Ni1 N2 C9 C4 26.39(19) . . . . ? C10 N2 C9 C8 23.8(2) . . . . ? Ni1 N2 C9 C8 -151.27(12) . . . . ? C7 C8 C9 C4 0.9(2) . . . . ? C7 C8 C9 N2 178.65(14) . . . . ? C9 N2 C10 O2 15.0(2) . . . . ? Ni1 N2 C10 O2 -169.37(14) . . . . ? C9 N2 C10 C11 -166.37(13) . . . . ? Ni1 N2 C10 C11 9.21(17) . . . . ? C12 N3 C11 C10 95.44(15) . . . . ? C14 N3 C11 C10 -148.66(15) . . . . ? Ni1 N3 C11 C10 -24.03(16) . . . . ? O2 C10 C11 N3 -170.56(15) . . . . ? N2 C10 C11 N3 10.7(2) . . . . ? C11 N3 C12 C13 -57.94(17) . . . . ? C14 N3 C12 C13 -174.78(14) . . . . ? Ni1 N3 C12 C13 59.80(15) . . . . ? C11 N3 C14 C15 69.87(19) . . . . ? C12 N3 C14 C15 -171.83(15) . . . . ? Ni1 N3 C14 C15 -49.73(19) . . . . ? N1 C1 C16 C17 -172.40(13) . . . . ? C2 C1 C16 C17 74.21(16) . . . . ? C1 C16 C17 C19A 52.5(4) . . . . ? C1 C16 C17 C18 -162.43(17) . . . . ? C1 C16 C17 C19B 83.3(2) . . . . ?