#------------------------------------------------------------------------------ #$Date: 2021-04-29 06:44:03 +0300 (Thu, 29 Apr 2021) $ #$Revision: 264679 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060619.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_7060619 loop_ _publ_author_name 'Castillo-Garc\'ia, Antonio Aldair' 'Lucero, Gonz\'alez-Sebasti\'an' 'Lomas-Romero, Leticia' 'Hernandez-Ortega, Simon' 'Toscano, Ruben Alfredo' 'Morales-Morales, David' _publ_section_title ; Novel meta-Benzothiazole and Benzimidazole Functionalised POCOP-Ni(II) Pincer Complexes as Efficient Catalysts in the Production of Diarylketones. ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ01348C _journal_year 2021 _chemical_formula_moiety 'C25 H35 Cl N2 Ni O2 P2' _chemical_formula_sum 'C25 H35 Cl N2 Ni O2 P2' _chemical_formula_weight 551.65 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2021-02-11 deposited with the CCDC. 2021-04-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.680(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.1985(11) _cell_length_b 15.1991(9) _cell_length_c 10.8855(6) _cell_measurement_reflns_used 9717 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.84 _cell_measurement_theta_min 2.35 _cell_volume 2752.6(3) _computing_cell_refinement 'APEX2 v2014.1-1(Bruker, 2014)' _computing_data_collection 'APEX2 v2014.1-1(Bruker, 2014)' _computing_data_reduction 'SAINT V8.34A (Bruker, 2014)' _computing_molecular_graphics 'XP V 5.1 (Bruker, 1998)' _computing_publication_material 'CIFTAB V 2013/2 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXS-2012 (Bruker, 2013)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 52.0833 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 Venture \k-geometry diffractometer 208039-01' _diffrn_measurement_method '\f and \w-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_unetI/netI 0.0313 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 68831 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.231 _diffrn_reflns_theta_min 2.353 _diffrn_source 'micro-focus X-ray source' _exptl_absorpt_coefficient_mu 0.942 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.6711 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Sheldrick, 2012)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.331 _exptl_crystal_description hexagonal-plate _exptl_crystal_F_000 1160 _exptl_crystal_size_max 0.339 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.048 _refine_diff_density_max 0.424 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 7454 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0423 _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^)+(0.0366P)^2^+2.2096P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0885 _refine_ls_wR_factor_ref 0.1037 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5258 _reflns_number_total 7454 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01348c2.cif _cod_data_source_block complex2a _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7060619 _shelx_shelxl_version_number 2016/6 _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 0.741 _shelx_estimated_absorpt_t_max 0.956 _shelx_res_file ; TITL complex2a complex2a.res created by SHELXL-2016/6 at 23:46:36 on 09-Feb-2021 CELL 0.71073 17.1985 15.1991 10.8855 90.000 104.680 90.000 ZERR 4.00 0.0011 0.0009 0.0006 0.000 0.002 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N O P CL NI UNIT 100 140 8 8 8 4 4 OMIT 6 3 0 OMIT 8 8 0 OMIT 9 6 3 OMIT -2 1 6 OMIT -6 3 6 LIST 4 TEMP 25.00 SIZE 0.048 0.220 0.339 ACTA L.S. 20 FMAP 2 PLAN 5 HTAB N7 O1 EQIV $1 x, -y+1/2, z+1/2 HTAB C22 Cl1_$1 HTAB C24 Cl1 BOND $H CONF WGHT 0.036600 2.209600 FVAR 0.12696 NI2 7 0.309579 0.470213 0.563345 11.00000 0.04563 0.03496 = 0.03038 0.00077 0.01622 0.00627 CL1 6 0.368402 0.421788 0.420987 11.00000 0.09164 0.07209 = 0.05468 -0.00290 0.04266 0.02275 P1 5 0.222788 0.556091 0.445554 11.00000 0.04614 0.04028 = 0.02487 -0.00022 0.01301 0.00578 P2 5 0.376190 0.389616 0.716145 11.00000 0.05071 0.04231 = 0.03853 0.00643 0.01715 0.01290 O1 4 0.182596 0.612880 0.544726 11.00000 0.05442 0.04861 = 0.02575 0.00367 0.01380 0.01705 O2 4 0.348502 0.421335 0.844146 11.00000 0.05271 0.05579 = 0.03594 0.01162 0.01683 0.01868 C1 1 0.291378 0.487317 0.816834 11.00000 0.03734 0.04036 = 0.03378 0.00254 0.01141 0.00325 C2 1 0.266160 0.516545 0.691989 11.00000 0.03755 0.03657 = 0.02760 -0.00078 0.01121 0.00156 C3 1 0.208557 0.582477 0.668525 11.00000 0.03682 0.03582 = 0.02564 -0.00086 0.00968 0.00057 C4 1 0.175088 0.618249 0.761294 11.00000 0.03413 0.03655 = 0.02723 -0.00366 0.00935 -0.00079 C5 1 0.203602 0.585357 0.884621 11.00000 0.04498 0.04855 = 0.02697 -0.00444 0.01377 0.00072 AFIX 43 H5 2 0.182773 0.607823 0.949094 11.00000 -1.20000 AFIX 0 C6 1 0.261310 0.521021 0.913372 11.00000 0.04632 0.05280 = 0.02602 0.00419 0.01044 0.00743 AFIX 43 H6 2 0.279819 0.500508 0.996138 11.00000 -1.20000 AFIX 0 N7 3 0.089165 0.732483 0.627498 11.00000 0.04409 0.04981 = 0.02774 -0.00336 0.01272 0.01065 H7 2 0.104533 0.726420 0.565838 11.00000 -1.20000 C8 1 0.112680 0.685878 0.737665 11.00000 0.03454 0.03777 = 0.02973 -0.00468 0.00929 -0.00090 N9 3 0.074326 0.711122 0.822807 11.00000 0.04321 0.04682 = 0.03635 -0.00127 0.01787 0.00701 C10 1 -0.032796 0.826482 0.808061 11.00000 0.05692 0.07280 = 0.04154 0.00089 0.02188 0.02278 AFIX 43 H10 2 -0.040389 0.817080 0.888640 11.00000 -1.20000 AFIX 0 C11 1 -0.075569 0.889653 0.729367 11.00000 0.06248 0.08733 = 0.05377 -0.00042 0.02023 0.03903 AFIX 43 H11 2 -0.113097 0.923139 0.757039 11.00000 -1.20000 AFIX 0 C12 1 -0.064250 0.904914 0.609216 11.00000 0.08099 0.09114 = 0.04995 0.01024 0.01506 0.04982 AFIX 43 H12 2 -0.093475 0.949293 0.559248 11.00000 -1.20000 AFIX 0 C13 1 -0.010775 0.855900 0.562277 11.00000 0.07152 0.08104 = 0.03608 0.00516 0.01524 0.03369 AFIX 43 H13 2 -0.003640 0.865534 0.481473 11.00000 -1.20000 AFIX 0 C14 1 0.031582 0.791862 0.641305 11.00000 0.04256 0.05402 = 0.03235 -0.00502 0.00975 0.01167 C15 1 0.022624 0.776609 0.763378 11.00000 0.04142 0.04782 = 0.03552 -0.00345 0.01336 0.00700 C16 1 0.133435 0.505700 0.342129 11.00000 0.05296 0.06968 = 0.04186 -0.01075 0.00642 -0.00007 AFIX 13 H16 2 0.099699 0.552190 0.293509 11.00000 -1.20000 AFIX 0 C17 1 0.086232 0.458748 0.422370 11.00000 0.07632 0.11438 = 0.09103 0.00590 0.01038 -0.04014 AFIX 137 H17A 2 0.038370 0.433891 0.368252 11.00000 -1.50000 H17B 2 0.071831 0.499888 0.479799 11.00000 -1.50000 H17C 2 0.118555 0.412684 0.469957 11.00000 -1.50000 AFIX 0 C18 1 0.154960 0.441241 0.250285 11.00000 0.09936 0.16169 = 0.10873 -0.09489 0.01668 -0.01866 AFIX 137 H18A 2 0.107288 0.411492 0.203925 11.00000 -1.50000 H18B 2 0.192645 0.398934 0.296531 11.00000 -1.50000 H18C 2 0.178619 0.472351 0.192059 11.00000 -1.50000 AFIX 0 C19 1 0.254245 0.648049 0.362125 11.00000 0.06168 0.05062 = 0.04902 0.01520 0.02480 0.01093 AFIX 13 H19 2 0.209949 0.690524 0.342301 11.00000 -1.20000 AFIX 0 C20 1 0.272828 0.622084 0.237986 11.00000 0.15217 0.11189 = 0.07014 0.02616 0.07471 0.01898 AFIX 137 H20A 2 0.225239 0.598882 0.181012 11.00000 -1.50000 H20B 2 0.314239 0.578100 0.254003 11.00000 -1.50000 H20C 2 0.290763 0.672843 0.200410 11.00000 -1.50000 AFIX 0 C21 1 0.325101 0.692677 0.448934 11.00000 0.11959 0.07770 = 0.10715 0.01359 0.02140 -0.04083 AFIX 137 H21A 2 0.370111 0.653159 0.467696 11.00000 -1.50000 H21B 2 0.311811 0.708985 0.526357 11.00000 -1.50000 H21C 2 0.338683 0.744420 0.408253 11.00000 -1.50000 AFIX 0 C22 1 0.353000 0.273132 0.710366 11.00000 0.11557 0.04101 = 0.06451 0.01371 0.02960 0.01011 AFIX 13 H22 2 0.373422 0.249090 0.796028 11.00000 -1.20000 AFIX 0 C23 1 0.262743 0.261899 0.673221 11.00000 0.13698 0.06906 = 0.16954 0.02330 0.01481 -0.04246 AFIX 137 H23A 2 0.241219 0.286176 0.590130 11.00000 -1.50000 H23B 2 0.239934 0.291940 0.733391 11.00000 -1.50000 H23C 2 0.249746 0.200446 0.672548 11.00000 -1.50000 AFIX 0 C24 1 0.394326 0.224229 0.621479 11.00000 0.25512 0.05545 = 0.10151 -0.00533 0.07468 0.04057 AFIX 137 H24A 2 0.379481 0.163218 0.617912 11.00000 -1.50000 H24B 2 0.451562 0.229507 0.652825 11.00000 -1.50000 H24C 2 0.377858 0.249289 0.537945 11.00000 -1.50000 AFIX 0 C25 1 0.484725 0.403397 0.766462 11.00000 0.05055 0.10061 = 0.05399 0.00827 0.02116 0.01965 AFIX 13 H25 2 0.507078 0.382128 0.697592 11.00000 -1.20000 AFIX 0 C26 1 0.523630 0.350439 0.885633 11.00000 0.06636 0.16078 = 0.08652 0.03326 0.00597 0.03504 AFIX 137 H26A 2 0.513678 0.288897 0.868908 11.00000 -1.50000 H26B 2 0.501112 0.368199 0.953936 11.00000 -1.50000 H26C 2 0.580523 0.360975 0.908868 11.00000 -1.50000 AFIX 0 C27 1 0.503625 0.500404 0.783714 11.00000 0.06944 0.11931 = 0.09580 -0.00448 0.02457 -0.02532 AFIX 137 H27A 2 0.480119 0.530969 0.705998 11.00000 -1.50000 H27B 2 0.560828 0.508672 0.805802 11.00000 -1.50000 H27C 2 0.481934 0.523193 0.850303 11.00000 -1.50000 REM ##### AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM complex2a REM R1 = 0.0423 for 5258 Fo > 4sig(Fo) and 0.0768 for all 7454 data REM 309 parameters refined using 0 restraints END WGHT 0.0366 2.2099 REM Highest difference peak 0.424, deepest hole -0.336, 1-sigma level 0.062 Q1 1 0.3611 0.4365 0.6540 11.00000 0.05 0.42 Q2 1 0.3584 0.4157 0.6263 11.00000 0.05 0.39 Q3 1 0.2688 0.5312 0.5264 11.00000 0.05 0.37 Q4 1 0.3973 0.4705 0.4572 11.00000 0.05 0.34 Q5 1 0.2725 0.5081 0.6215 11.00000 0.05 0.34 ; _shelx_res_checksum 68177 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, 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 Ni2 Ni 0.30958(2) 0.47021(2) 0.56334(3) 0.03580(9) Uani 1 1 d . . . . . Cl1 Cl 0.36840(5) 0.42179(5) 0.42099(7) 0.0684(2) Uani 1 1 d . . . . . P1 P 0.22279(4) 0.55609(4) 0.44555(5) 0.03637(14) Uani 1 1 d . . . . . P2 P 0.37619(4) 0.38962(4) 0.71614(6) 0.04279(15) Uani 1 1 d . . . . . O1 O 0.18260(10) 0.61288(11) 0.54473(13) 0.0423(4) Uani 1 1 d . . . . . O2 O 0.34850(10) 0.42133(12) 0.84415(15) 0.0471(4) Uani 1 1 d . . . . . C1 C 0.29138(13) 0.48732(15) 0.8168(2) 0.0367(5) Uani 1 1 d . . . . . C2 C 0.26616(13) 0.51654(14) 0.69199(19) 0.0334(4) Uani 1 1 d . . . . . C3 C 0.20856(13) 0.58248(14) 0.66853(18) 0.0324(4) Uani 1 1 d . . . . . C4 C 0.17509(13) 0.61825(14) 0.76129(19) 0.0324(4) Uani 1 1 d . . . . . C5 C 0.20360(14) 0.58536(16) 0.8846(2) 0.0393(5) Uani 1 1 d . . . . . H5 H 0.182773 0.607823 0.949094 0.047 Uiso 1 1 calc R U . . . C6 C 0.26131(14) 0.52102(16) 0.9134(2) 0.0415(5) Uani 1 1 d . . . . . H6 H 0.279819 0.500508 0.996138 0.050 Uiso 1 1 calc R U . . . N7 N 0.08916(12) 0.73248(13) 0.62750(17) 0.0399(4) Uani 1 1 d . . . . . H7 H 0.1045(16) 0.7264(18) 0.566(2) 0.048 Uiso 1 1 d . U . . . C8 C 0.11268(13) 0.68588(14) 0.73766(19) 0.0338(4) Uani 1 1 d . . . . . N9 N 0.07433(12) 0.71112(13) 0.82281(17) 0.0407(4) Uani 1 1 d . . . . . C10 C -0.03280(16) 0.8265(2) 0.8081(2) 0.0554(7) Uani 1 1 d . . . . . H10 H -0.040389 0.817080 0.888640 0.066 Uiso 1 1 calc R U . . . C11 C -0.07557(18) 0.8897(2) 0.7294(3) 0.0669(9) Uani 1 1 d . . . . . H11 H -0.113097 0.923139 0.757039 0.080 Uiso 1 1 calc R U . . . C12 C -0.0642(2) 0.9049(2) 0.6092(3) 0.0743(10) Uani 1 1 d . . . . . H12 H -0.093475 0.949293 0.559248 0.089 Uiso 1 1 calc R U . . . C13 C -0.01078(18) 0.8559(2) 0.5623(2) 0.0626(8) Uani 1 1 d . . . . . H13 H -0.003640 0.865534 0.481473 0.075 Uiso 1 1 calc R U . . . C14 C 0.03158(14) 0.79186(17) 0.6413(2) 0.0429(5) Uani 1 1 d . . . . . C15 C 0.02262(14) 0.77661(16) 0.7634(2) 0.0409(5) Uani 1 1 d . . . . . C16 C 0.13343(17) 0.5057(2) 0.3421(2) 0.0558(7) Uani 1 1 d . . . . . H16 H 0.099699 0.552190 0.293509 0.067 Uiso 1 1 calc R U . . . C17 C 0.0862(2) 0.4587(3) 0.4224(4) 0.0959(13) Uani 1 1 d . . . . . H17A H 0.038370 0.433891 0.368252 0.144 Uiso 1 1 calc R U . . . H17B H 0.071831 0.499888 0.479799 0.144 Uiso 1 1 calc R U . . . H17C H 0.118555 0.412684 0.469957 0.144 Uiso 1 1 calc R U . . . C18 C 0.1550(3) 0.4412(3) 0.2503(4) 0.1250(19) Uani 1 1 d . . . . . H18A H 0.107288 0.411492 0.203925 0.188 Uiso 1 1 calc R U . . . H18B H 0.192645 0.398934 0.296531 0.188 Uiso 1 1 calc R U . . . H18C H 0.178619 0.472351 0.192059 0.188 Uiso 1 1 calc R U . . . C19 C 0.25425(17) 0.64805(18) 0.3621(2) 0.0518(6) Uani 1 1 d . . . . . H19 H 0.209949 0.690524 0.342301 0.062 Uiso 1 1 calc R U . . . C20 C 0.2728(3) 0.6221(3) 0.2380(3) 0.1030(14) Uani 1 1 d . . . . . H20A H 0.225239 0.598882 0.181012 0.154 Uiso 1 1 calc R U . . . H20B H 0.314239 0.578100 0.254003 0.154 Uiso 1 1 calc R U . . . H20C H 0.290763 0.672843 0.200410 0.154 Uiso 1 1 calc R U . . . C21 C 0.3251(3) 0.6927(3) 0.4489(4) 0.1028(14) Uani 1 1 d . . . . . H21A H 0.370111 0.653159 0.467696 0.154 Uiso 1 1 calc R U . . . H21B H 0.311811 0.708985 0.526357 0.154 Uiso 1 1 calc R U . . . H21C H 0.338683 0.744420 0.408253 0.154 Uiso 1 1 calc R U . . . C22 C 0.3530(2) 0.27313(19) 0.7104(3) 0.0725(9) Uani 1 1 d . . . . . H22 H 0.373422 0.249090 0.796028 0.087 Uiso 1 1 calc R U . . . C23 C 0.2627(3) 0.2619(3) 0.6732(5) 0.1295(19) Uani 1 1 d . . . . . H23A H 0.241219 0.286176 0.590130 0.194 Uiso 1 1 calc R U . . . H23B H 0.239934 0.291940 0.733391 0.194 Uiso 1 1 calc R U . . . H23C H 0.249746 0.200446 0.672548 0.194 Uiso 1 1 calc R U . . . C24 C 0.3943(4) 0.2242(3) 0.6215(4) 0.132(2) Uani 1 1 d . . . . . H24A H 0.379481 0.163218 0.617912 0.198 Uiso 1 1 calc R U . . . H24B H 0.451562 0.229507 0.652825 0.198 Uiso 1 1 calc R U . . . H24C H 0.377858 0.249289 0.537945 0.198 Uiso 1 1 calc R U . . . C25 C 0.48472(18) 0.4034(2) 0.7665(3) 0.0670(9) Uani 1 1 d . . . . . H25 H 0.507078 0.382128 0.697592 0.080 Uiso 1 1 calc R U . . . C26 C 0.5236(2) 0.3504(3) 0.8856(4) 0.1070(15) Uani 1 1 d . . . . . H26A H 0.513678 0.288897 0.868908 0.160 Uiso 1 1 calc R U . . . H26B H 0.501112 0.368199 0.953936 0.160 Uiso 1 1 calc R U . . . H26C H 0.580523 0.360975 0.908868 0.160 Uiso 1 1 calc R U . . . C27 C 0.5036(2) 0.5004(3) 0.7837(4) 0.0942(12) Uani 1 1 d . . . . . H27A H 0.480119 0.530969 0.705998 0.141 Uiso 1 1 calc R U . . . H27B H 0.560828 0.508672 0.805802 0.141 Uiso 1 1 calc R U . . . H27C H 0.481934 0.523193 0.850303 0.141 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 Ni2 0.04563(17) 0.03496(15) 0.03038(14) 0.00077(11) 0.01622(12) 0.00627(12) Cl1 0.0916(6) 0.0721(5) 0.0547(4) -0.0029(3) 0.0427(4) 0.0228(4) P1 0.0461(3) 0.0403(3) 0.0249(3) -0.0002(2) 0.0130(2) 0.0058(3) P2 0.0507(4) 0.0423(3) 0.0385(3) 0.0064(3) 0.0172(3) 0.0129(3) O1 0.0544(10) 0.0486(9) 0.0257(7) 0.0037(6) 0.0138(7) 0.0170(8) O2 0.0527(10) 0.0558(10) 0.0359(8) 0.0116(7) 0.0168(7) 0.0187(8) C1 0.0373(12) 0.0404(12) 0.0338(11) 0.0025(9) 0.0114(9) 0.0032(9) C2 0.0375(11) 0.0366(11) 0.0276(10) -0.0008(8) 0.0112(8) 0.0016(9) C3 0.0368(11) 0.0358(11) 0.0256(9) -0.0009(8) 0.0097(8) 0.0006(9) C4 0.0341(11) 0.0365(11) 0.0272(10) -0.0037(8) 0.0094(8) -0.0008(9) C5 0.0450(13) 0.0486(13) 0.0270(10) -0.0044(9) 0.0138(9) 0.0007(10) C6 0.0463(13) 0.0528(14) 0.0260(10) 0.0042(10) 0.0104(9) 0.0074(11) N7 0.0441(11) 0.0498(12) 0.0277(9) -0.0034(8) 0.0127(8) 0.0107(9) C8 0.0345(11) 0.0378(11) 0.0297(10) -0.0047(9) 0.0093(9) -0.0009(9) N9 0.0432(11) 0.0468(11) 0.0363(10) -0.0013(8) 0.0179(8) 0.0070(9) C10 0.0569(16) 0.0728(18) 0.0415(13) 0.0009(13) 0.0219(12) 0.0228(14) C11 0.0625(18) 0.087(2) 0.0538(16) -0.0004(15) 0.0202(14) 0.0390(16) C12 0.081(2) 0.091(2) 0.0500(16) 0.0102(16) 0.0151(15) 0.0498(19) C13 0.0715(19) 0.081(2) 0.0361(13) 0.0052(13) 0.0152(13) 0.0337(16) C14 0.0426(13) 0.0540(14) 0.0323(11) -0.0050(10) 0.0098(10) 0.0117(11) C15 0.0414(12) 0.0478(13) 0.0355(11) -0.0035(10) 0.0134(10) 0.0070(10) C16 0.0530(16) 0.0697(18) 0.0419(14) -0.0108(13) 0.0064(12) -0.0001(13) C17 0.076(2) 0.114(3) 0.091(3) 0.006(2) 0.010(2) -0.040(2) C18 0.099(3) 0.162(4) 0.109(3) -0.095(3) 0.017(3) -0.019(3) C19 0.0617(16) 0.0506(15) 0.0490(14) 0.0152(12) 0.0248(13) 0.0109(13) C20 0.152(4) 0.112(3) 0.070(2) 0.026(2) 0.075(3) 0.019(3) C21 0.120(3) 0.078(3) 0.107(3) 0.014(2) 0.021(3) -0.041(2) C22 0.116(3) 0.0410(16) 0.0645(19) 0.0137(14) 0.0296(19) 0.0101(17) C23 0.137(4) 0.069(3) 0.170(5) 0.023(3) 0.015(4) -0.042(3) C24 0.255(7) 0.055(2) 0.102(3) -0.005(2) 0.075(4) 0.041(3) C25 0.0506(16) 0.101(3) 0.0540(16) 0.0083(16) 0.0212(13) 0.0197(16) C26 0.066(2) 0.161(4) 0.087(3) 0.033(3) 0.006(2) 0.035(3) C27 0.069(2) 0.119(3) 0.096(3) -0.004(3) 0.025(2) -0.025(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' P P 0.1023 0.0942 '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 C2 Ni2 P1 82.53(7) . . ? C2 Ni2 P2 82.62(7) . . ? P1 Ni2 P2 164.41(3) . . ? C2 Ni2 Cl1 175.63(7) . . ? P1 Ni2 Cl1 99.11(3) . . ? P2 Ni2 Cl1 96.04(3) . . ? O1 P1 C19 98.64(10) . . ? O1 P1 C16 101.21(11) . . ? C19 P1 C16 108.91(13) . . ? O1 P1 Ni2 105.57(6) . . ? C19 P1 Ni2 120.99(9) . . ? C16 P1 Ni2 117.53(11) . . ? O2 P2 C22 101.90(13) . . ? O2 P2 C25 101.84(12) . . ? C22 P2 C25 108.84(17) . . ? O2 P2 Ni2 105.97(6) . . ? C22 P2 Ni2 117.43(12) . . ? C25 P2 Ni2 118.21(11) . . ? C3 O1 P1 111.92(13) . . ? C1 O2 P2 111.77(13) . . ? C6 C1 O2 119.20(19) . . ? C6 C1 C2 122.7(2) . . ? O2 C1 C2 118.07(19) . . ? C3 C2 C1 116.25(19) . . ? C3 C2 Ni2 122.20(15) . . ? C1 C2 Ni2 121.55(16) . . ? C2 C3 O1 117.31(17) . . ? C2 C3 C4 123.75(19) . . ? O1 C3 C4 118.93(18) . . ? C3 C4 C5 116.6(2) . . ? C3 C4 C8 124.53(19) . . ? C5 C4 C8 118.90(18) . . ? C6 C5 C4 122.1(2) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C1 118.6(2) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C8 N7 C14 107.82(18) . . ? C8 N7 H7 127(2) . . ? C14 N7 H7 125(2) . . ? N9 C8 N7 112.09(19) . . ? N9 C8 C4 123.71(19) . . ? N7 C8 C4 124.16(18) . . ? C8 N9 C15 104.88(18) . . ? C11 C10 C15 117.9(2) . . ? C11 C10 H10 121.1 . . ? C15 C10 H10 121.1 . . ? C10 C11 C12 121.6(2) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C13 C12 C11 121.6(3) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 116.5(2) . . ? C12 C13 H13 121.7 . . ? C14 C13 H13 121.7 . . ? N7 C14 C13 132.5(2) . . ? N7 C14 C15 104.6(2) . . ? C13 C14 C15 122.9(2) . . ? N9 C15 C14 110.63(19) . . ? N9 C15 C10 130.0(2) . . ? C14 C15 C10 119.4(2) . . ? C18 C16 C17 109.5(3) . . ? C18 C16 P1 111.8(2) . . ? C17 C16 P1 109.4(2) . . ? C18 C16 H16 108.7 . . ? C17 C16 H16 108.7 . . ? P1 C16 H16 108.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C19 C20 110.9(3) . . ? C21 C19 P1 109.2(2) . . ? C20 C19 P1 113.6(2) . . ? C21 C19 H19 107.6 . . ? C20 C19 H19 107.6 . . ? P1 C19 H19 107.6 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C24 112.7(4) . . ? C23 C22 P2 108.8(2) . . ? C24 C22 P2 111.3(3) . . ? C23 C22 H22 108.0 . . ? C24 C22 H22 108.0 . . ? P2 C22 H22 108.0 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C27 C25 C26 112.0(3) . . ? C27 C25 P2 108.8(2) . . ? C26 C25 P2 112.9(2) . . ? C27 C25 H25 107.6 . . ? C26 C25 H25 107.6 . . ? P2 C25 H25 107.6 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 Ni2 C2 1.883(2) . ? Ni2 P1 2.1461(6) . ? Ni2 P2 2.1480(7) . ? Ni2 Cl1 2.1820(7) . ? P1 O1 1.6633(15) . ? P1 C19 1.822(3) . ? P1 C16 1.827(3) . ? P2 O2 1.6544(17) . ? P2 C22 1.812(3) . ? P2 C25 1.819(3) . ? O1 C3 1.387(2) . ? O2 C1 1.382(3) . ? C1 C6 1.382(3) . ? C1 C2 1.391(3) . ? C2 C3 1.387(3) . ? C3 C4 1.393(3) . ? C4 C5 1.400(3) . ? C4 C8 1.461(3) . ? C5 C6 1.372(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N7 C8 1.363(3) . ? N7 C14 1.376(3) . ? N7 H7 0.79(3) . ? C8 N9 1.323(3) . ? N9 C15 1.381(3) . ? C10 C11 1.370(4) . ? C10 C15 1.398(3) . ? C10 H10 0.9300 . ? C11 C12 1.390(4) . ? C11 H11 0.9300 . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 C14 1.379(4) . ? C13 H13 0.9300 . ? C14 C15 1.395(3) . ? C16 C18 1.511(4) . ? C16 C17 1.513(4) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C21 1.501(5) . ? C19 C20 1.518(4) . ? C19 H19 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.511(6) . ? C22 C24 1.530(5) . ? C22 H22 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C27 1.511(5) . ? C25 C26 1.529(5) . ? C25 H25 0.9800 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? 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 N7 H7 O1 0.79(3) 2.23(3) 2.726(2) 121(2) . C22 H22 Cl1 0.98 2.94 3.714(3) 136.3 4_566 C24 H24C Cl1 0.96 2.90 3.672(4) 138.1 . 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 C19 P1 O1 C3 -132.58(16) . . . . ? C16 P1 O1 C3 116.06(17) . . . . ? Ni2 P1 O1 C3 -6.92(16) . . . . ? C22 P2 O2 C1 -122.37(19) . . . . ? C25 P2 O2 C1 125.21(19) . . . . ? Ni2 P2 O2 C1 1.00(17) . . . . ? P2 O2 C1 C6 179.59(18) . . . . ? P2 O2 C1 C2 0.1(3) . . . . ? C6 C1 C2 C3 0.2(3) . . . . ? O2 C1 C2 C3 179.71(19) . . . . ? C6 C1 C2 Ni2 179.10(18) . . . . ? O2 C1 C2 Ni2 -1.4(3) . . . . ? P1 Ni2 C2 C3 -4.35(18) . . . . ? P2 Ni2 C2 C3 -179.59(19) . . . . ? P1 Ni2 C2 C1 176.81(19) . . . . ? P2 Ni2 C2 C1 1.57(18) . . . . ? C1 C2 C3 O1 179.84(19) . . . . ? Ni2 C2 C3 O1 0.9(3) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? Ni2 C2 C3 C4 179.95(17) . . . . ? P1 O1 C3 C2 4.5(2) . . . . ? P1 O1 C3 C4 -174.58(16) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? O1 C3 C4 C5 -179.8(2) . . . . ? C2 C3 C4 C8 -178.1(2) . . . . ? O1 C3 C4 C8 0.9(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C8 C4 C5 C6 179.1(2) . . . . ? C4 C5 C6 C1 -0.7(4) . . . . ? O2 C1 C6 C5 -178.8(2) . . . . ? C2 C1 C6 C5 0.7(4) . . . . ? C14 N7 C8 N9 -0.2(3) . . . . ? C14 N7 C8 C4 -178.0(2) . . . . ? C3 C4 C8 N9 171.1(2) . . . . ? C5 C4 C8 N9 -8.2(3) . . . . ? C3 C4 C8 N7 -11.4(3) . . . . ? C5 C4 C8 N7 169.3(2) . . . . ? N7 C8 N9 C15 0.9(3) . . . . ? C4 C8 N9 C15 178.7(2) . . . . ? C15 C10 C11 C12 -0.6(5) . . . . ? C10 C11 C12 C13 1.5(6) . . . . ? C11 C12 C13 C14 -0.8(5) . . . . ? C8 N7 C14 C13 178.2(3) . . . . ? C8 N7 C14 C15 -0.6(3) . . . . ? C12 C13 C14 N7 -179.2(3) . . . . ? C12 C13 C14 C15 -0.6(5) . . . . ? C8 N9 C15 C14 -1.2(3) . . . . ? C8 N9 C15 C10 179.6(3) . . . . ? N7 C14 C15 N9 1.1(3) . . . . ? C13 C14 C15 N9 -177.8(3) . . . . ? N7 C14 C15 C10 -179.6(2) . . . . ? C13 C14 C15 C10 1.5(4) . . . . ? C11 C10 C15 N9 178.3(3) . . . . ? C11 C10 C15 C14 -0.8(4) . . . . ? O1 P1 C16 C18 -173.6(3) . . . . ? C19 P1 C16 C18 83.1(3) . . . . ? Ni2 P1 C16 C18 -59.3(3) . . . . ? O1 P1 C16 C17 -52.2(3) . . . . ? C19 P1 C16 C17 -155.5(2) . . . . ? Ni2 P1 C16 C17 62.1(3) . . . . ? O1 P1 C19 C21 72.0(3) . . . . ? C16 P1 C19 C21 177.1(2) . . . . ? Ni2 P1 C19 C21 -42.0(3) . . . . ? O1 P1 C19 C20 -163.5(2) . . . . ? C16 P1 C19 C20 -58.5(3) . . . . ? Ni2 P1 C19 C20 82.4(3) . . . . ? O2 P2 C22 C23 70.9(3) . . . . ? C25 P2 C22 C23 178.0(3) . . . . ? Ni2 P2 C22 C23 -44.3(3) . . . . ? O2 P2 C22 C24 -164.4(3) . . . . ? C25 P2 C22 C24 -57.3(3) . . . . ? Ni2 P2 C22 C24 80.4(3) . . . . ? O2 P2 C25 C27 -67.4(2) . . . . ? C22 P2 C25 C27 -174.5(2) . . . . ? Ni2 P2 C25 C27 48.2(3) . . . . ? O2 P2 C25 C26 57.5(3) . . . . ? C22 P2 C25 C26 -49.6(3) . . . . ? Ni2 P2 C25 C26 173.1(2) . . . . ?