#------------------------------------------------------------------------------ #$Date: 2020-03-04 09:42:00 +0200 (Wed, 04 Mar 2020) $ #$Revision: 248749 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557443.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_1557443 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 'C20 H28 N2 Ni O6' _chemical_formula_sum 'C20 H28 N2 Ni O6' _chemical_formula_weight 451.15 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _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 108.791(8) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.3939(4) _cell_length_b 14.9329(8) _cell_length_c 8.7611(6) _cell_measurement_reflns_used 11415 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.7 _cell_volume 1039.63(11) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 93(2) _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type ; Olex2 1.2 (compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0888 _diffrn_reflns_av_unetI/netI 0.0370 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 20757 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.008 _diffrn_reflns_theta_max 25.008 _diffrn_reflns_theta_min 3.226 _diffrn_source 'Sealed Tube' _exptl_absorpt_coefficient_mu 0.972 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.778 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Olex2 1.2 (compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506) ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.441 _exptl_crystal_description plate _exptl_crystal_F_000 476 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.303 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 1829 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0418 _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^)+(0.0241P)^2^+1.4103P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0800 _refine_ls_wR_factor_ref 0.0846 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1536 _reflns_number_total 1829 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05565g2.cif _cod_data_source_block spider-16039 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1557443 _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 0.829 _shelx_estimated_absorpt_t_max 0.953 _shelx_res_file ; spider-16039.res created by SHELXL-2014/7 TITL spider-16039 CELL 0.71075 8.3939 14.9329 8.7611 90 108.791 90 ZERR 2 0.0004 0.0008 0.0006 0 0.008 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N Ni O UNIT 40 56 4 2 12 L.S. 10 CONF MORE -1 ACTA TEMP -180 BOND $H LIST 6 MORE -1 CONF SIZE 0.20 0.20 0.05 WGHT 0.024100 1.410300 FVAR 0.88414 NI1 4 0.500000 0.500000 0.500000 10.50000 0.01974 0.01982 = 0.02561 -0.00012 0.00816 -0.00094 O1 5 0.756976 0.514570 0.544240 11.00000 0.02281 0.02530 = 0.02851 -0.00347 0.00841 -0.00005 H1 2 0.751211 0.531676 0.445857 11.00000 0.05784 O2 5 0.553567 0.440093 0.724596 11.00000 0.02957 0.03148 = 0.03095 0.00176 0.01177 0.00041 O3 5 0.294710 0.435167 0.745460 11.00000 0.03273 0.04623 = 0.03651 -0.00083 0.01463 -0.00512 N1 3 0.537144 0.623757 0.604347 11.00000 0.02133 0.02096 = 0.02274 0.00277 0.00719 0.00193 C1 1 0.413266 0.679484 0.612117 11.00000 0.02099 0.03003 = 0.02574 0.00277 0.00756 0.00404 AFIX 43 H1A 2 0.300400 0.658575 0.574481 11.00000 -1.20000 AFIX 0 C2 1 0.443493 0.765735 0.672506 11.00000 0.02908 0.02689 = 0.02838 0.00157 0.01139 0.00688 AFIX 43 H2 2 0.353367 0.803577 0.674946 11.00000 -1.20000 AFIX 0 C3 1 0.607864 0.795338 0.729063 11.00000 0.03280 0.02246 = 0.03167 0.00044 0.01068 0.00016 AFIX 43 H3 2 0.632612 0.854222 0.771065 11.00000 -1.20000 AFIX 0 C4 1 0.736077 0.738655 0.724095 11.00000 0.02350 0.02665 = 0.03260 0.00020 0.00906 -0.00448 AFIX 43 H4 2 0.849835 0.758009 0.764027 11.00000 -1.20000 AFIX 0 C5 1 0.697734 0.653221 0.660399 11.00000 0.02443 0.02369 = 0.02038 0.00093 0.00758 -0.00311 C6 1 0.833306 0.586689 0.653243 11.00000 0.02243 0.02189 = 0.03233 -0.00141 0.00843 -0.00282 C7 1 0.914646 0.545715 0.819837 11.00000 0.02928 0.02711 = 0.03699 -0.00250 0.00331 0.00284 AFIX 137 H7A 2 0.830278 0.511457 0.850781 11.00000 -1.50000 H7B 2 0.959474 0.593534 0.898602 11.00000 -1.50000 H7C 2 1.006421 0.505841 0.817111 11.00000 -1.50000 AFIX 0 C8 1 0.968198 0.631513 0.595398 11.00000 0.02920 0.03034 = 0.04991 -0.00748 0.01877 -0.00374 AFIX 137 H8A 2 0.914182 0.661779 0.492411 11.00000 -1.50000 H8B 2 1.046235 0.585931 0.581191 11.00000 -1.50000 H8C 2 1.030291 0.675444 0.675664 11.00000 -1.50000 AFIX 0 C9 1 0.452222 0.423396 0.801677 11.00000 0.04023 0.02349 = 0.03055 -0.00251 0.01357 -0.00538 C10 1 0.525095 0.388011 0.972141 11.00000 0.05513 0.02913 = 0.03160 0.00279 0.01387 0.00046 AFIX 137 H10A 2 0.630162 0.419623 1.027532 11.00000 -1.50000 H10B 2 0.547801 0.323787 0.968905 11.00000 -1.50000 H10C 2 0.444460 0.397735 1.030252 11.00000 -1.50000 AFIX 0 HKLF 4 REM spider-16039 REM R1 = 0.0418 for 1536 Fo > 4sig(Fo) and 0.0538 for all 1829 data REM 140 parameters refined using 0 restraints END WGHT 0.0237 1.4124 REM Highest difference peak 0.303, deepest hole -0.335, 1-sigma level 0.061 Q1 1 0.7683 0.6195 0.6619 11.00000 0.05 0.30 Q2 1 0.5022 0.4220 1.0552 11.00000 0.05 0.27 Q3 1 0.7224 0.6818 0.7398 11.00000 0.05 0.24 Q4 1 0.5516 0.3954 0.6221 11.00000 0.05 0.23 Q5 1 0.5295 0.3834 0.5923 11.00000 0.05 0.22 Q6 1 0.8369 0.4856 0.8529 11.00000 0.05 0.21 Q7 1 0.6271 0.6363 0.6554 11.00000 0.05 0.20 Q8 1 0.6005 0.6640 0.5878 11.00000 0.05 0.20 Q9 1 0.6855 0.7630 0.7578 11.00000 0.05 0.20 Q10 1 0.8062 0.8623 0.7982 11.00000 0.05 0.20 Q11 1 0.3728 0.5961 0.4790 11.00000 0.05 0.20 Q12 1 0.5312 0.5258 0.7177 11.00000 0.05 0.20 Q13 1 0.6255 0.3443 0.9859 11.00000 0.05 0.20 Q14 1 1.0571 0.7204 0.8240 11.00000 0.05 0.20 Q15 1 0.5442 0.4391 1.2021 11.00000 0.05 0.20 Q16 1 0.5548 0.4844 1.0925 11.00000 0.05 0.20 Q17 1 0.7037 0.3645 1.0446 11.00000 0.05 0.19 Q18 1 0.7003 0.4810 0.5999 11.00000 0.05 0.19 Q19 1 0.5264 0.7627 0.7251 11.00000 0.05 0.19 Q20 1 0.6789 0.4443 0.6397 11.00000 0.05 0.19 ; _shelx_res_checksum 4771 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.02152(16) Uani 1 2 d S . P . . O1 O 0.7570(2) 0.51457(13) 0.5442(2) 0.0255(5) Uani 1 1 d . . . . . H1 H 0.751(5) 0.532(2) 0.446(5) 0.058(12) Uiso 1 1 d . . . . . O2 O 0.5536(2) 0.44009(13) 0.7246(2) 0.0302(5) Uani 1 1 d . . . . . O3 O 0.2947(3) 0.43517(15) 0.7455(3) 0.0377(5) Uani 1 1 d . . . . . N1 N 0.5371(3) 0.62376(14) 0.6043(3) 0.0217(5) Uani 1 1 d . . . . . C1 C 0.4133(3) 0.67948(19) 0.6121(3) 0.0256(6) Uani 1 1 d . . . . . H1A H 0.3004 0.6586 0.5745 0.031 Uiso 1 1 calc R U . . . C2 C 0.4435(4) 0.76574(19) 0.6725(3) 0.0276(7) Uani 1 1 d . . . . . H2 H 0.3534 0.8036 0.6749 0.033 Uiso 1 1 calc R U . . . C3 C 0.6079(4) 0.79534(19) 0.7291(3) 0.0289(7) Uani 1 1 d . . . . . H3 H 0.6326 0.8542 0.7711 0.035 Uiso 1 1 calc R U . . . C4 C 0.7361(4) 0.73865(18) 0.7241(3) 0.0276(7) Uani 1 1 d . . . . . H4 H 0.8498 0.7580 0.7640 0.033 Uiso 1 1 calc R U . . . C5 C 0.6977(3) 0.65322(18) 0.6604(3) 0.0227(6) Uani 1 1 d . . . . . C6 C 0.8333(3) 0.58669(18) 0.6532(3) 0.0256(6) Uani 1 1 d . . . . . C7 C 0.9146(4) 0.5457(2) 0.8198(4) 0.0329(7) Uani 1 1 d . . . . . H7A H 0.8303 0.5115 0.8508 0.049 Uiso 1 1 calc R U . . . H7B H 0.9595 0.5935 0.8986 0.049 Uiso 1 1 calc R U . . . H7C H 1.0064 0.5058 0.8171 0.049 Uiso 1 1 calc R U . . . C8 C 0.9682(4) 0.6315(2) 0.5954(4) 0.0350(8) Uani 1 1 d . . . . . H8A H 0.9142 0.6618 0.4924 0.053 Uiso 1 1 calc R U . . . H8B H 1.0462 0.5859 0.5812 0.053 Uiso 1 1 calc R U . . . H8C H 1.0303 0.6754 0.6757 0.053 Uiso 1 1 calc R U . . . C9 C 0.4522(4) 0.42340(19) 0.8017(4) 0.0309(7) Uani 1 1 d . . . . . C10 C 0.5251(4) 0.3880(2) 0.9721(4) 0.0386(8) Uani 1 1 d . . . . . H10A H 0.6302 0.4196 1.0275 0.058 Uiso 1 1 calc R U . . . H10B H 0.5478 0.3238 0.9689 0.058 Uiso 1 1 calc R U . . . H10C H 0.4445 0.3977 1.0303 0.058 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 0.0197(3) 0.0198(3) 0.0256(3) -0.0001(2) 0.0082(2) -0.0009(2) O1 0.0228(10) 0.0253(11) 0.0285(11) -0.0035(9) 0.0084(8) -0.0001(8) O2 0.0296(11) 0.0315(11) 0.0310(11) 0.0018(9) 0.0118(9) 0.0004(9) O3 0.0327(13) 0.0462(14) 0.0365(13) -0.0008(10) 0.0146(10) -0.0051(10) N1 0.0213(12) 0.0210(12) 0.0227(12) 0.0028(10) 0.0072(10) 0.0019(10) C1 0.0210(15) 0.0300(16) 0.0257(15) 0.0028(12) 0.0076(12) 0.0040(12) C2 0.0291(16) 0.0269(16) 0.0284(16) 0.0016(13) 0.0114(13) 0.0069(13) C3 0.0328(17) 0.0225(15) 0.0317(17) 0.0004(13) 0.0107(13) 0.0002(13) C4 0.0235(15) 0.0266(16) 0.0326(17) 0.0002(13) 0.0091(13) -0.0045(12) C5 0.0244(15) 0.0237(15) 0.0204(14) 0.0009(12) 0.0076(12) -0.0031(12) C6 0.0224(15) 0.0219(15) 0.0323(16) -0.0014(12) 0.0084(12) -0.0028(12) C7 0.0293(17) 0.0271(16) 0.0370(18) -0.0025(14) 0.0033(14) 0.0028(13) C8 0.0292(17) 0.0303(17) 0.050(2) -0.0075(15) 0.0188(15) -0.0037(13) C9 0.0402(19) 0.0235(16) 0.0306(17) -0.0025(13) 0.0136(15) -0.0054(14) C10 0.055(2) 0.0291(17) 0.0316(18) 0.0028(14) 0.0139(16) 0.0005(15) 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' Ni Ni 0.3393 1.1124 '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' 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 N1 Ni1 N1 180.0 . 3_666 ? N1 Ni1 O2 90.60(8) . . ? N1 Ni1 O2 89.40(8) 3_666 . ? N1 Ni1 O2 89.40(8) . 3_666 ? N1 Ni1 O2 90.60(8) 3_666 3_666 ? O2 Ni1 O2 180.0 . 3_666 ? N1 Ni1 O1 100.26(8) . 3_666 ? N1 Ni1 O1 79.74(8) 3_666 3_666 ? O2 Ni1 O1 91.52(8) . 3_666 ? O2 Ni1 O1 88.48(8) 3_666 3_666 ? N1 Ni1 O1 79.74(8) . . ? N1 Ni1 O1 100.26(8) 3_666 . ? O2 Ni1 O1 88.48(8) . . ? O2 Ni1 O1 91.52(8) 3_666 . ? O1 Ni1 O1 180.0 3_666 . ? C6 O1 Ni1 114.47(15) . . ? C6 O1 H1 108(2) . . ? Ni1 O1 H1 97(2) . . ? C9 O2 Ni1 127.70(19) . . ? C1 N1 C5 118.4(2) . . ? C1 N1 Ni1 124.86(19) . . ? C5 N1 Ni1 116.64(17) . . ? N1 C1 C2 122.9(3) . . ? N1 C1 H1A 118.5 . . ? C2 C1 H1A 118.5 . . ? C3 C2 C1 118.3(3) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 121.4(3) . . ? N1 C5 C6 116.3(2) . . ? C4 C5 C6 122.4(2) . . ? O1 C6 C7 107.4(2) . . ? O1 C6 C5 109.5(2) . . ? C7 C6 C5 109.3(2) . . ? O1 C6 C8 108.9(2) . . ? C7 C6 C8 109.9(2) . . ? C5 C6 C8 111.6(2) . . ? 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 . . ? O3 C9 O2 124.1(3) . . ? O3 C9 C10 118.1(3) . . ? O2 C9 C10 117.8(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 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 N1 2.041(2) . ? Ni1 N1 2.041(2) 3_666 ? Ni1 O2 2.0747(19) . ? Ni1 O2 2.0747(19) 3_666 ? Ni1 O1 2.0765(18) 3_666 ? Ni1 O1 2.0765(18) . ? O1 C6 1.445(3) . ? O1 H1 0.89(4) . ? O2 C9 1.270(3) . ? O3 C9 1.266(4) . ? N1 C1 1.351(3) . ? N1 C5 1.351(3) . ? C1 C2 1.384(4) . ? C1 H1A 0.9500 . ? C2 C3 1.380(4) . ? C2 H2 0.9500 . ? C3 C4 1.381(4) . ? C3 H3 0.9500 . ? C4 C5 1.388(4) . ? C4 H4 0.9500 . ? C5 C6 1.527(4) . ? C6 C7 1.526(4) . ? C6 C8 1.535(4) . ? 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 1.515(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 C5 N1 C1 C2 1.1(4) . . . . ? Ni1 N1 C1 C2 -174.7(2) . . . . ? N1 C1 C2 C3 -0.9(4) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C1 N1 C5 C4 -0.3(4) . . . . ? Ni1 N1 C5 C4 175.8(2) . . . . ? C1 N1 C5 C6 178.3(2) . . . . ? Ni1 N1 C5 C6 -5.6(3) . . . . ? C3 C4 C5 N1 -0.7(4) . . . . ? C3 C4 C5 C6 -179.2(3) . . . . ? Ni1 O1 C6 C7 98.6(2) . . . . ? Ni1 O1 C6 C5 -20.1(3) . . . . ? Ni1 O1 C6 C8 -142.40(19) . . . . ? N1 C5 C6 O1 16.8(3) . . . . ? C4 C5 C6 O1 -164.6(3) . . . . ? N1 C5 C6 C7 -100.7(3) . . . . ? C4 C5 C6 C7 77.9(3) . . . . ? N1 C5 C6 C8 137.5(3) . . . . ? C4 C5 C6 C8 -44.0(4) . . . . ? Ni1 O2 C9 O3 5.8(4) . . . . ? Ni1 O2 C9 C10 -173.61(19) . . . . ?