#------------------------------------------------------------------------------ #$Date: 2020-03-04 09:42:00 +0200 (Wed, 04 Mar 2020) $ #$Revision: 248749 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557444.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_1557444 loop_ _publ_author_name 'Fisher, Katherine J.' 'Feuer, Margalit L.' 'Lant, Hannah M. C.' 'Mercado, Brandon Q.' 'Crabtree, Robert H.' 'Brudvig, Gary W.' _publ_section_title ; Concerted proton-electron transfer oxidation of phenols and hydrocarbons by a high-valent nickel complex ; _journal_issue 6 _journal_name_full 'Chemical Science' _journal_page_first 1683 _journal_paper_doi 10.1039/C9SC05565G _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C26 H30 N4 Ni O2, F6 P, C5 H5 N' _chemical_formula_sum 'C31 H35 F6 N5 Ni O2 P' _chemical_formula_weight 713.32 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-I 2ya' _space_group_name_H-M_alt 'I 1 2/a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary SHELXT _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-09-17 deposited with the CCDC. 2019-12-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.646(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 22.4997(12) _cell_length_b 8.4913(3) _cell_length_c 17.7726(7) _cell_measurement_reflns_used 15415 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 66.1460 _cell_measurement_theta_min 4.1760 _cell_volume 3156.0(3) _computing_cell_refinement 'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'CIFTAB-2014/2 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT-2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 93(2) _diffrn_detector_area_resol_mean 22.2 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Rigaku Saturn 944+ CCD' _diffrn_measurement_method \w _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0908 _diffrn_reflns_av_unetI/netI 0.0282 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 54705 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 66.893 _diffrn_reflns_theta_max 66.893 _diffrn_reflns_theta_min 4.228 _diffrn_source 'microfocus rotating anode' _exptl_absorpt_coefficient_mu 2.017 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.71733 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.501 _exptl_crystal_description Plate _exptl_crystal_F_000 1476 _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.487 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.071 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 214 _refine_ls_number_reflns 2801 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0526 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+10.3170P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1320 _refine_ls_wR_factor_ref 0.1434 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2231 _reflns_number_total 2801 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05565g2.cif _cod_data_source_block 007a-18050 _cod_original_sg_symbol_H-M 'I 2/a' _cod_database_code 1557444 _shelx_shelxl_version_number 2014/7 _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 0.824 _shelx_estimated_absorpt_t_max 0.906 _shelx_res_file ; 007a-18050.res created by SHELXL-2014/7 TITL 007a-18050 CELL 1.54184 22.499732 8.49125 17.772589 90 111.6462 90 ZERR 4 0.001208 0.00033 0.000737 0 0.0054 0 LATT 2 SYMM 0.5-X,+Y,-Z SFAC C H F N Ni O P UNIT 124 140 24 20 4 8 4 L.S. 10 CONF MORE -1 ACTA BOND $H SIZE 0.1 0.1 0.05 TEMP -180 BOND $H WGHT 0.063200 10.317000 FVAR 0.26543 NI1 5 0.500000 0.500000 0.500000 10.50000 0.03783 0.03054 = 0.02318 -0.00028 0.01389 0.00109 O1 6 0.509998 0.643657 0.581307 11.00000 0.03958 0.03445 = 0.02538 -0.00139 0.01432 0.00240 N1 4 0.431935 0.414284 0.528566 11.00000 0.03820 0.03336 = 0.02485 -0.00001 0.01271 0.00039 N2 4 0.565377 0.342794 0.587813 11.00000 0.03898 0.03403 = 0.02739 0.00284 0.01453 0.00279 C1 1 0.396103 0.289902 0.493315 11.00000 0.04641 0.03729 = 0.03206 0.00209 0.01771 0.00006 AFIX 43 H1 2 0.399256 0.248043 0.445356 11.00000 -1.20000 AFIX 0 C2 1 0.354693 0.220432 0.524396 11.00000 0.04605 0.04118 = 0.04713 0.00468 0.01868 -0.00566 AFIX 43 H2 2 0.329243 0.132589 0.498405 11.00000 -1.20000 AFIX 0 C3 1 0.351400 0.283054 0.594934 11.00000 0.04949 0.05518 = 0.04734 0.01084 0.02755 0.00051 AFIX 43 H3 2 0.324223 0.236530 0.618854 11.00000 -1.20000 AFIX 0 C4 1 0.387789 0.413182 0.630132 11.00000 0.04696 0.05031 = 0.03411 0.00361 0.02458 0.00307 AFIX 43 H4 2 0.385457 0.457143 0.678121 11.00000 -1.20000 AFIX 0 C5 1 0.427951 0.479878 0.595073 11.00000 0.03908 0.03876 = 0.02692 0.00452 0.01359 0.00788 C6 1 0.468294 0.625883 0.624507 11.00000 0.04256 0.03946 = 0.02717 -0.00261 0.01674 -0.00006 C7 1 0.508935 0.613453 0.715019 11.00000 0.04998 0.07167 = 0.02786 -0.00400 0.01532 -0.00203 AFIX 137 H7A 2 0.533000 0.514432 0.725560 11.00000 -1.50000 H7B 2 0.480981 0.615721 0.746207 11.00000 -1.50000 H7C 2 0.538806 0.702260 0.731154 11.00000 -1.50000 AFIX 0 C8 1 0.424633 0.770566 0.609064 11.00000 0.04885 0.04464 = 0.04655 -0.00983 0.02368 0.00404 AFIX 137 H8A 2 0.450816 0.865868 0.625545 11.00000 -1.50000 H8B 2 0.397001 0.761360 0.640477 11.00000 -1.50000 H8C 2 0.398176 0.776948 0.551300 11.00000 -1.50000 AFIX 0 C9 1 0.557132 0.185820 0.583386 11.00000 0.04903 0.03096 = 0.03393 -0.00303 0.01508 0.00331 AFIX 43 H9 2 0.522811 0.142778 0.539016 11.00000 -1.20000 AFIX 0 C10 1 0.596586 0.085475 0.640758 11.00000 0.06010 0.03307 = 0.03878 0.00461 0.02494 0.00954 AFIX 43 H10 2 0.589063 -0.024851 0.636577 11.00000 -1.20000 AFIX 0 C11 1 0.646965 0.146442 0.704144 11.00000 0.04873 0.04036 = 0.03420 0.01174 0.02015 0.01371 AFIX 43 H11 2 0.675433 0.078988 0.743829 11.00000 -1.20000 AFIX 0 C12 1 0.655597 0.308022 0.709272 11.00000 0.03625 0.04568 = 0.03418 0.00541 0.00923 0.00285 AFIX 43 H12 2 0.689807 0.353434 0.752925 11.00000 -1.20000 AFIX 0 C13 1 0.613909 0.401707 0.650232 11.00000 0.03496 0.03819 = 0.03410 0.00091 0.01237 -0.00166 AFIX 43 H13 2 0.619867 0.512601 0.654001 11.00000 -1.20000 AFIX 0 P1 7 0.750000 0.750000 0.750000 10.50000 0.04162 0.02757 = 0.03099 -0.00062 0.01498 0.00183 F1 3 0.674215 0.762782 0.723968 11.00000 0.04262 0.04176 = 0.04958 -0.00386 0.01590 0.00298 F2 3 0.751812 0.616019 0.813757 11.00000 0.06486 0.03530 = 0.04371 0.00978 0.02523 0.00714 F3 3 0.759019 0.881372 0.817586 11.00000 0.05390 0.03772 = 0.03953 -0.00995 0.01693 0.00094 N14 4 0.250000 0.911945 0.500000 10.50000 0.06770 0.04745 = 0.06498 0.00000 0.01499 0.00000 C15 1 0.259944 0.830562 0.438952 11.00000 0.04402 0.05797 = 0.03013 0.00667 0.01602 -0.00777 AFIX 43 H15 2 0.265052 0.885975 0.395292 11.00000 -1.20000 AFIX 0 C16 1 0.262452 0.672267 0.440994 11.00000 0.04192 0.07889 = 0.04922 -0.03489 0.01244 0.00422 AFIX 43 H16 2 0.272896 0.616075 0.401313 11.00000 -1.20000 AFIX 0 C17 1 0.250000 0.592873 0.500000 10.50000 0.05038 0.04843 = 0.12785 0.00000 -0.00940 0.00000 AFIX 43 H17 2 0.250000 0.480993 0.500000 10.50000 -1.20000 AFIX 0 HKLF 4 REM 007a-18050 REM R1 = 0.0526 for 2231 Fo > 4sig(Fo) and 0.0692 for all 2801 data REM 214 parameters refined using 0 restraints END WGHT 0.0632 10.3167 REM Highest difference peak 0.487, deepest hole -0.512, 1-sigma level 0.071 Q1 1 0.5607 0.5016 0.5310 11.00000 0.05 0.49 Q2 1 0.4965 0.0000 0.5269 11.00000 0.05 0.40 Q3 1 0.2633 0.6615 0.4740 11.00000 0.05 0.37 Q4 1 0.2558 0.7554 0.4390 11.00000 0.05 0.32 Q5 1 0.6874 0.7520 0.6980 11.00000 0.05 0.30 Q6 1 0.2672 0.7994 0.4131 11.00000 0.05 0.28 Q7 1 0.7512 0.5902 0.7780 11.00000 0.05 0.27 Q8 1 0.7577 0.9036 0.7872 11.00000 0.05 0.26 Q9 1 0.5673 0.6592 0.6120 11.00000 0.05 0.25 Q10 1 0.5107 0.3491 0.5478 11.00000 0.05 0.24 Q11 1 0.4960 0.1466 0.4486 11.00000 0.05 0.24 Q12 1 0.4298 0.6336 0.6909 11.00000 0.05 0.23 Q13 1 0.3498 0.2560 0.5518 11.00000 0.05 0.22 Q14 1 0.5453 0.3790 0.5458 11.00000 0.05 0.21 Q15 1 0.5021 0.6753 0.5063 11.00000 0.05 0.21 Q16 1 0.3684 0.2645 0.5121 11.00000 0.05 0.21 Q17 1 0.7588 0.8072 0.8282 11.00000 0.05 0.20 Q18 1 0.7542 0.6889 0.8251 11.00000 0.05 0.20 Q19 1 0.5396 0.8079 0.6000 11.00000 0.05 0.20 Q20 1 0.5009 0.8545 0.6168 11.00000 0.05 0.20 ; _shelx_res_checksum 48324 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' '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 Ni1 Ni 0.5000 0.5000 0.5000 0.0298(2) Uani 1 2 d S . P . . O1 O 0.51000(11) 0.6437(3) 0.58131(13) 0.0325(5) Uani 1 1 d . . . . . N1 N 0.43194(13) 0.4143(3) 0.52857(16) 0.0318(6) Uani 1 1 d . . . . . N2 N 0.56538(13) 0.3428(3) 0.58781(16) 0.0328(7) Uani 1 1 d . . . . . C1 C 0.39610(18) 0.2899(4) 0.4933(2) 0.0377(8) Uani 1 1 d . . . . . H1 H 0.3993 0.2480 0.4454 0.045 Uiso 1 1 calc R U . . . C2 C 0.35469(19) 0.2204(5) 0.5244(2) 0.0444(9) Uani 1 1 d . . . . . H2 H 0.3292 0.1326 0.4984 0.053 Uiso 1 1 calc R U . . . C3 C 0.3514(2) 0.2831(5) 0.5949(2) 0.0479(10) Uani 1 1 d . . . . . H3 H 0.3242 0.2365 0.6189 0.057 Uiso 1 1 calc R U . . . C4 C 0.38779(18) 0.4132(5) 0.6301(2) 0.0411(9) Uani 1 1 d . . . . . H4 H 0.3855 0.4571 0.6781 0.049 Uiso 1 1 calc R U . . . C5 C 0.42795(17) 0.4799(4) 0.5951(2) 0.0345(8) Uani 1 1 d . . . . . C6 C 0.46829(17) 0.6259(4) 0.6245(2) 0.0353(8) Uani 1 1 d . . . . . C7 C 0.5089(2) 0.6135(6) 0.7150(2) 0.0496(10) Uani 1 1 d . . . . . H7A H 0.5330 0.5144 0.7256 0.074 Uiso 1 1 calc R U . . . H7B H 0.4810 0.6157 0.7462 0.074 Uiso 1 1 calc R U . . . H7C H 0.5388 0.7023 0.7312 0.074 Uiso 1 1 calc R U . . . C8 C 0.42463(19) 0.7706(5) 0.6091(2) 0.0449(10) Uani 1 1 d . . . . . H8A H 0.4508 0.8659 0.6255 0.067 Uiso 1 1 calc R U . . . H8B H 0.3970 0.7614 0.6405 0.067 Uiso 1 1 calc R U . . . H8C H 0.3982 0.7769 0.5513 0.067 Uiso 1 1 calc R U . . . C9 C 0.55713(18) 0.1858(4) 0.5834(2) 0.0380(8) Uani 1 1 d . . . . . H9 H 0.5228 0.1428 0.5390 0.046 Uiso 1 1 calc R U . . . C10 C 0.59659(19) 0.0855(5) 0.6408(2) 0.0421(9) Uani 1 1 d . . . . . H10 H 0.5891 -0.0249 0.6366 0.050 Uiso 1 1 calc R U . . . C11 C 0.64696(18) 0.1464(5) 0.7041(2) 0.0397(9) Uani 1 1 d . . . . . H11 H 0.6754 0.0790 0.7438 0.048 Uiso 1 1 calc R U . . . C12 C 0.65560(18) 0.3080(5) 0.7093(2) 0.0398(9) Uani 1 1 d . . . . . H12 H 0.6898 0.3534 0.7529 0.048 Uiso 1 1 calc R U . . . C13 C 0.61391(16) 0.4017(5) 0.6502(2) 0.0359(8) Uani 1 1 d . . . . . H13 H 0.6199 0.5126 0.6540 0.043 Uiso 1 1 calc R U . . . P1 P 0.7500 0.7500 0.7500 0.0329(3) Uani 1 2 d S . P . . F1 F 0.67421(10) 0.7628(2) 0.72397(13) 0.0450(5) Uani 1 1 d . . . . . F2 F 0.75181(11) 0.6160(3) 0.81376(13) 0.0465(6) Uani 1 1 d . . . . . F3 F 0.75902(10) 0.8814(2) 0.81759(12) 0.0438(5) Uani 1 1 d . . . . . N14 N 0.2500 0.9119(7) 0.5000 0.0627(14) Uani 1 2 d S T P . . C15 C 0.25994(18) 0.8306(5) 0.4390(2) 0.0434(9) Uani 1 1 d . . . . . H15 H 0.2651 0.8860 0.3953 0.052 Uiso 1 1 calc R U . . . C16 C 0.2625(2) 0.6723(6) 0.4410(3) 0.0579(13) Uani 1 1 d . . . . . H16 H 0.2729 0.6161 0.4013 0.070 Uiso 1 1 calc R U . . . C17 C 0.2500 0.5929(9) 0.5000 0.088(3) Uani 1 2 d S T P . . H17 H 0.2500 0.4810 0.5000 0.105 Uiso 1 2 calc R U P . . 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 0.0378(5) 0.0305(5) 0.0232(4) -0.0003(3) 0.0139(3) 0.0011(4) O1 0.0396(13) 0.0345(13) 0.0254(11) -0.0014(10) 0.0143(10) 0.0024(10) N1 0.0382(15) 0.0334(16) 0.0248(14) 0.0000(12) 0.0127(12) 0.0004(13) N2 0.0390(16) 0.0340(17) 0.0274(14) 0.0028(12) 0.0145(12) 0.0028(13) C1 0.046(2) 0.037(2) 0.0321(18) 0.0021(16) 0.0177(16) 0.0001(17) C2 0.046(2) 0.041(2) 0.047(2) 0.0047(18) 0.0187(18) -0.0057(18) C3 0.049(2) 0.055(3) 0.047(2) 0.0108(19) 0.0276(19) 0.001(2) C4 0.047(2) 0.050(2) 0.0341(19) 0.0036(17) 0.0246(17) 0.0031(18) C5 0.0391(19) 0.039(2) 0.0269(16) 0.0045(15) 0.0136(14) 0.0079(16) C6 0.043(2) 0.039(2) 0.0272(17) -0.0026(15) 0.0167(15) -0.0001(16) C7 0.050(2) 0.072(3) 0.0279(19) -0.0040(19) 0.0153(17) -0.002(2) C8 0.049(2) 0.045(2) 0.047(2) -0.0098(18) 0.0237(18) 0.0040(18) C9 0.049(2) 0.031(2) 0.0339(18) -0.0030(15) 0.0151(16) 0.0033(16) C10 0.060(2) 0.033(2) 0.039(2) 0.0046(16) 0.0249(18) 0.0095(18) C11 0.049(2) 0.040(2) 0.0342(19) 0.0117(16) 0.0201(17) 0.0137(17) C12 0.0363(19) 0.046(2) 0.0342(18) 0.0054(17) 0.0092(15) 0.0028(17) C13 0.0350(18) 0.038(2) 0.0341(18) 0.0009(15) 0.0124(15) -0.0017(16) P1 0.0416(7) 0.0276(7) 0.0310(6) -0.0006(5) 0.0150(5) 0.0018(5) F1 0.0426(12) 0.0418(13) 0.0496(13) -0.0039(10) 0.0159(10) 0.0030(10) F2 0.0649(14) 0.0353(12) 0.0437(12) 0.0098(10) 0.0252(11) 0.0071(10) F3 0.0539(13) 0.0377(12) 0.0395(11) -0.0099(9) 0.0169(10) 0.0009(10) N14 0.068(4) 0.047(3) 0.065(3) 0.000 0.015(3) 0.000 C15 0.044(2) 0.058(3) 0.0301(18) 0.0067(18) 0.0160(16) -0.0078(19) C16 0.042(2) 0.079(4) 0.049(3) -0.035(2) 0.012(2) 0.004(2) C17 0.050(4) 0.048(4) 0.128(8) 0.000 -0.009(5) 0.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 O1 Ni1 O1 180.0 5_666 . ? O1 Ni1 N1 94.46(11) 5_666 . ? O1 Ni1 N1 85.54(11) . . ? O1 Ni1 N1 85.54(11) 5_666 5_666 ? O1 Ni1 N1 94.46(11) . 5_666 ? N1 Ni1 N1 180.00(14) . 5_666 ? O1 Ni1 N2 90.64(10) 5_666 . ? O1 Ni1 N2 89.36(10) . . ? N1 Ni1 N2 88.39(11) . . ? N1 Ni1 N2 91.61(11) 5_666 . ? O1 Ni1 N2 89.37(10) 5_666 5_666 ? O1 Ni1 N2 90.63(10) . 5_666 ? N1 Ni1 N2 91.61(11) . 5_666 ? N1 Ni1 N2 88.39(11) 5_666 5_666 ? N2 Ni1 N2 180.0 . 5_666 ? C6 O1 Ni1 116.1(2) . . ? C1 N1 C5 121.2(3) . . ? C1 N1 Ni1 125.2(2) . . ? C5 N1 Ni1 113.2(2) . . ? C13 N2 C9 118.3(3) . . ? C13 N2 Ni1 119.9(2) . . ? C9 N2 Ni1 121.8(2) . . ? N1 C1 C2 122.0(3) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C1 C2 C3 117.8(4) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 119.7(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 119.4(3) . . ? N1 C5 C6 114.8(3) . . ? C4 C5 C6 125.8(3) . . ? O1 C6 C5 109.4(3) . . ? O1 C6 C7 108.5(3) . . ? C5 C6 C7 110.9(3) . . ? O1 C6 C8 109.0(3) . . ? C5 C6 C8 109.4(3) . . ? C7 C6 C8 109.7(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 122.3(4) . . ? N2 C9 H9 118.8 . . ? C10 C9 H9 118.8 . . ? C11 C10 C9 119.2(4) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 118.8(3) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C13 C12 C11 118.9(4) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? N2 C13 C12 122.5(4) . . ? N2 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? F2 P1 F2 180.0 7_666 . ? F2 P1 F3 90.06(11) 7_666 7_666 ? F2 P1 F3 89.94(11) . 7_666 ? F2 P1 F3 89.94(11) 7_666 . ? F2 P1 F3 90.06(11) . . ? F3 P1 F3 180.00(11) 7_666 . ? F2 P1 F1 90.06(11) 7_666 . ? F2 P1 F1 89.95(12) . . ? F3 P1 F1 90.21(11) 7_666 . ? F3 P1 F1 89.79(11) . . ? F2 P1 F1 89.94(12) 7_666 7_666 ? F2 P1 F1 90.06(11) . 7_666 ? F3 P1 F1 89.79(11) 7_666 7_666 ? F3 P1 F1 90.21(11) . 7_666 ? F1 P1 F1 180.0 . 7_666 ? C15 N14 C15 119.5(5) . 2_556 ? C16 C15 N14 119.9(4) . . ? C16 C15 H15 120.0 . . ? N14 C15 H15 120.0 . . ? C15 C16 C17 119.8(5) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C16 120.6(7) . 2_556 ? C16 C17 H17 119.7 . . ? C16 C17 H17 119.7 2_556 . ? 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 O1 1.840(2) 5_666 ? Ni1 O1 1.840(2) . ? Ni1 N1 1.925(3) . ? Ni1 N1 1.925(3) 5_666 ? Ni1 N2 2.165(3) . ? Ni1 N2 2.165(3) 5_666 ? O1 C6 1.423(4) . ? N1 C1 1.336(5) . ? N1 C5 1.339(4) . ? N2 C13 1.334(4) . ? N2 C9 1.344(5) . ? C1 C2 1.379(5) . ? C1 H1 0.9500 . ? C2 C3 1.389(6) . ? C2 H2 0.9500 . ? C3 C4 1.380(6) . ? C3 H3 0.9500 . ? C4 C5 1.393(5) . ? C4 H4 0.9500 . ? C5 C6 1.511(5) . ? C6 C7 1.533(5) . ? C6 C8 1.533(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.373(5) . ? C9 H9 0.9500 . ? C10 C11 1.371(6) . ? C10 H10 0.9500 . ? C11 C12 1.384(6) . ? C11 H11 0.9500 . ? C12 C13 1.374(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? P1 F2 1.596(2) 7_666 ? P1 F2 1.596(2) . ? P1 F3 1.596(2) 7_666 ? P1 F3 1.596(2) . ? P1 F1 1.597(2) . ? P1 F1 1.597(2) 7_666 ? N14 C15 1.373(5) . ? N14 C15 1.373(5) 2_556 ? C15 C16 1.345(7) . ? C15 H15 0.9500 . ? C16 C17 1.360(6) . ? C16 H16 0.9500 . ? C17 C16 1.360(6) 2_556 ? C17 H17 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 N1 Ni1 O1 C6 1.1(2) . . . . ? N1 Ni1 O1 C6 -178.9(2) 5_666 . . . ? N2 Ni1 O1 C6 -87.3(2) . . . . ? N2 Ni1 O1 C6 92.6(2) 5_666 . . . ? C5 N1 C1 C2 -1.7(6) . . . . ? Ni1 N1 C1 C2 170.1(3) . . . . ? N1 C1 C2 C3 -0.5(6) . . . . ? C1 C2 C3 C4 1.6(6) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C1 N1 C5 C4 2.8(5) . . . . ? Ni1 N1 C5 C4 -170.0(3) . . . . ? C1 N1 C5 C6 -176.2(3) . . . . ? Ni1 N1 C5 C6 11.0(4) . . . . ? C3 C4 C5 N1 -1.6(6) . . . . ? C3 C4 C5 C6 177.2(3) . . . . ? Ni1 O1 C6 C5 4.2(3) . . . . ? Ni1 O1 C6 C7 125.3(3) . . . . ? Ni1 O1 C6 C8 -115.3(3) . . . . ? N1 C5 C6 O1 -10.0(4) . . . . ? C4 C5 C6 O1 171.1(3) . . . . ? N1 C5 C6 C7 -129.5(3) . . . . ? C4 C5 C6 C7 51.6(5) . . . . ? N1 C5 C6 C8 109.3(3) . . . . ? C4 C5 C6 C8 -69.6(4) . . . . ? C13 N2 C9 C10 0.3(5) . . . . ? Ni1 N2 C9 C10 -177.0(3) . . . . ? N2 C9 C10 C11 -1.2(6) . . . . ? C9 C10 C11 C12 1.5(5) . . . . ? C10 C11 C12 C13 -0.8(5) . . . . ? C9 N2 C13 C12 0.5(5) . . . . ? Ni1 N2 C13 C12 177.7(3) . . . . ? C11 C12 C13 N2 -0.2(6) . . . . ? C15 N14 C15 C16 -2.7(3) 2_556 . . . ? N14 C15 C16 C17 5.3(6) . . . . ? C15 C16 C17 C16 -2.7(3) . . . 2_556 ?