#------------------------------------------------------------------------------ #$Date: 2020-03-04 09:42:00 +0200 (Wed, 04 Mar 2020) $ #$Revision: 248749 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557442.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_1557442 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 'C16 H20 N2 Ni O2' _chemical_formula_sum 'C16 H20 N2 Ni O2' _chemical_formula_weight 331.05 _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 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 141.27(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 14.557(3) _cell_length_b 10.2366(5) _cell_length_c 8.2137(14) _cell_measurement_reflns_used 17033 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 66.7830 _cell_measurement_theta_min 5.6480 _cell_volume 765.8(7) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0690 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 21932 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 66.757 _diffrn_reflns_theta_max 66.757 _diffrn_reflns_theta_min 5.698 _diffrn_source 'microfocus rotating anode' _exptl_absorpt_coefficient_mu 1.871 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.75022 _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 Green _exptl_crystal_density_diffrn 1.436 _exptl_crystal_description Plate _exptl_crystal_F_000 348 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.284 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 99 _refine_ls_number_reflns 1361 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0281 _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^)+(0.0353P)^2^+0.5259P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.0733 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1234 _reflns_number_total 1361 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05565g2.cif _cod_data_source_block 007a-17123 _cod_original_cell_volume 765.8(4) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1557442 _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 0.706 _shelx_estimated_absorpt_t_max 0.706 _shelx_res_file ; 007a-17123.res created by SHELXL-2014/7 TITL 007a-17123 CELL 1.54184 14.5572 10.2366 8.2137 90 141.271 90 ZERR 2 0.0025 0.0005 0.0014 0 0.035 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N Ni O UNIT 32 40 4 2 4 L.S. 10 TEMP -180 SIZE 0.20 0.20 0.20 CONF MORE -1 ACTA BOND $H WGHT 0.035300 0.525900 FVAR 0.80110 NI1 4 0.500000 0.500000 0.500000 10.50000 0.01397 0.01694 = 0.01435 0.00191 0.01171 0.00264 O1 5 0.619780 0.414905 0.810888 11.00000 0.01775 0.02571 = 0.01843 0.00635 0.01515 0.00788 N1 3 0.616602 0.423743 0.499559 11.00000 0.01502 0.01462 = 0.01611 -0.00002 0.01242 -0.00065 C1 1 0.588289 0.423420 0.299065 11.00000 0.01886 0.01822 = 0.01718 0.00199 0.01463 0.00178 AFIX 43 H1 2 0.499888 0.461959 0.138602 11.00000 -1.20000 AFIX 0 C5 1 0.740295 0.367320 0.727325 11.00000 0.01627 0.01500 = 0.01732 -0.00107 0.01307 -0.00125 C6 1 0.754749 0.372542 0.931187 11.00000 0.01691 0.02354 = 0.01681 0.00313 0.01358 0.00505 C4 1 0.842163 0.312218 0.761938 11.00000 0.01986 0.02258 = 0.02175 0.00359 0.01673 0.00460 AFIX 43 H4 2 0.930066 0.274264 0.923968 11.00000 -1.20000 AFIX 0 C2 1 0.684040 0.368728 0.320413 11.00000 0.02593 0.02312 = 0.02334 0.00231 0.02149 0.00350 AFIX 43 H2 2 0.662021 0.368782 0.176915 11.00000 -1.20000 AFIX 0 C3 1 0.813402 0.313600 0.556889 11.00000 0.02446 0.02608 = 0.02848 0.00349 0.02307 0.00569 AFIX 43 H3 2 0.882037 0.276884 0.577678 11.00000 -1.20000 AFIX 0 C7 1 0.791126 0.235627 1.046397 11.00000 0.03388 0.03244 = 0.02949 0.01531 0.02778 0.01717 AFIX 137 H7A 2 0.797808 0.238401 1.174667 11.00000 -1.50000 H7B 2 0.885176 0.206612 1.131125 11.00000 -1.50000 H7C 2 0.713608 0.174497 0.906918 11.00000 -1.50000 AFIX 0 C8 1 0.876122 0.469597 1.143500 11.00000 0.01994 0.04318 = 0.02102 -0.00905 0.01415 -0.00054 AFIX 137 H8A 2 0.853768 0.555011 1.064746 11.00000 -1.50000 H8B 2 0.970270 0.438061 1.231324 11.00000 -1.50000 H8C 2 0.882043 0.477861 1.270372 11.00000 -1.50000 AFIX 0 HKLF 4 REM 007a-17123 REM R1 = 0.0281 for 1234 Fo > 4sig(Fo) and 0.0318 for all 1361 data REM 99 parameters refined using 0 restraints END WGHT 0.0354 0.5285 REM Highest difference peak 0.284, deepest hole -0.224, 1-sigma level 0.050 Q1 1 0.7426 0.3690 0.8240 11.00000 0.05 0.28 Q2 1 0.6028 0.4157 0.4137 11.00000 0.05 0.24 Q3 1 0.6784 0.3925 0.6137 11.00000 0.05 0.24 Q4 1 0.5622 0.4133 0.5018 11.00000 0.05 0.23 Q5 1 0.8168 0.3145 0.6528 11.00000 0.05 0.21 Q6 1 0.6780 0.3909 0.8613 11.00000 0.05 0.21 Q7 1 0.7978 0.3639 0.7486 11.00000 0.05 0.20 Q8 1 0.4168 0.4137 0.3518 11.00000 0.05 0.20 Q9 1 0.8083 0.4269 1.0173 11.00000 0.05 0.20 Q10 1 0.6330 0.3687 0.3105 11.00000 0.05 0.19 Q11 1 0.4782 0.4903 0.6011 11.00000 0.05 0.18 Q12 1 0.7708 0.3078 0.9902 11.00000 0.05 0.18 Q13 1 0.7382 0.3093 0.4254 11.00000 0.05 0.17 Q14 1 0.7660 0.3657 0.4552 11.00000 0.05 0.16 Q15 1 0.6310 0.5851 0.8318 11.00000 0.05 0.16 Q16 1 0.7515 0.2082 1.0784 11.00000 0.05 0.16 Q17 1 0.6339 0.4766 0.7391 11.00000 0.05 0.16 Q18 1 0.8753 0.2502 1.2639 11.00000 0.05 0.16 Q19 1 0.8350 0.1745 1.0585 11.00000 0.05 0.14 Q20 1 0.5748 0.3949 0.7120 11.00000 0.05 0.13 ; _shelx_res_checksum 64989 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 0.01420(15) Uani 1 2 d S . P . . O1 O 0.61978(12) 0.41491(12) 0.8109(2) 0.0192(3) Uani 1 1 d . . . . . N1 N 0.61660(15) 0.42374(13) 0.4996(3) 0.0149(3) Uani 1 1 d . . . . . C1 C 0.58829(19) 0.42342(16) 0.2991(3) 0.0173(4) Uani 1 1 d . . . . . H1 H 0.4999 0.4620 0.1386 0.021 Uiso 1 1 calc R U . . . C5 C 0.74030(18) 0.36732(16) 0.7273(3) 0.0162(4) Uani 1 1 d . . . . . C6 C 0.75475(18) 0.37254(18) 0.9312(3) 0.0185(4) Uani 1 1 d . . . . . C4 C 0.84216(19) 0.31222(18) 0.7619(3) 0.0207(4) Uani 1 1 d . . . . . H4 H 0.9301 0.2743 0.9240 0.025 Uiso 1 1 calc R U . . . C2 C 0.68404(19) 0.36873(17) 0.3204(3) 0.0211(4) Uani 1 1 d . . . . . H2 H 0.6620 0.3688 0.1769 0.025 Uiso 1 1 calc R U . . . C3 C 0.8134(2) 0.31360(18) 0.5569(4) 0.0231(4) Uani 1 1 d . . . . . H3 H 0.8820 0.2769 0.5777 0.028 Uiso 1 1 calc R U . . . C7 C 0.7911(2) 0.2356(2) 1.0464(4) 0.0279(4) Uani 1 1 d . . . . . H7A H 0.7978 0.2384 1.1747 0.042 Uiso 1 1 calc R U . . . H7B H 0.8852 0.2066 1.1311 0.042 Uiso 1 1 calc R U . . . H7C H 0.7136 0.1745 0.9069 0.042 Uiso 1 1 calc R U . . . C8 C 0.8761(2) 0.4696(2) 1.1435(4) 0.0305(5) Uani 1 1 d . . . . . H8A H 0.8538 0.5550 1.0647 0.046 Uiso 1 1 calc R U . . . H8B H 0.9703 0.4381 1.2313 0.046 Uiso 1 1 calc R U . . . H8C H 0.8820 0.4779 1.2704 0.046 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 0.0140(2) 0.0169(2) 0.0143(2) 0.00191(16) 0.0117(2) 0.00264(15) O1 0.0178(6) 0.0257(7) 0.0184(6) 0.0063(5) 0.0152(5) 0.0079(5) N1 0.0150(7) 0.0146(7) 0.0161(7) 0.0000(6) 0.0124(6) -0.0006(5) C1 0.0189(8) 0.0182(9) 0.0172(8) 0.0020(7) 0.0146(7) 0.0018(7) C5 0.0163(8) 0.0150(8) 0.0173(8) -0.0011(7) 0.0131(7) -0.0013(6) C6 0.0169(8) 0.0235(9) 0.0168(8) 0.0031(7) 0.0136(8) 0.0050(7) C4 0.0199(8) 0.0226(9) 0.0218(9) 0.0036(7) 0.0167(8) 0.0046(7) C2 0.0259(9) 0.0231(9) 0.0233(9) 0.0023(7) 0.0215(9) 0.0035(7) C3 0.0245(9) 0.0261(10) 0.0285(9) 0.0035(8) 0.0231(9) 0.0057(8) C7 0.0339(10) 0.0324(11) 0.0295(10) 0.0153(9) 0.0278(9) 0.0172(9) C8 0.0199(9) 0.0432(12) 0.0210(9) -0.0090(9) 0.0142(8) -0.0005(9) 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' 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' 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 3_666 . ? O1 Ni1 N1 94.24(6) 3_666 . ? O1 Ni1 N1 85.76(6) . . ? O1 Ni1 N1 85.76(6) 3_666 3_666 ? O1 Ni1 N1 94.24(6) . 3_666 ? N1 Ni1 N1 180.0 . 3_666 ? C6 O1 Ni1 114.33(10) . . ? C5 N1 C1 119.84(14) . . ? C5 N1 Ni1 114.04(11) . . ? C1 N1 Ni1 126.11(12) . . ? N1 C1 C2 121.93(16) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? N1 C5 C4 120.87(16) . . ? N1 C5 C6 113.66(14) . . ? C4 C5 C6 125.46(16) . . ? O1 C6 C5 108.61(14) . . ? O1 C6 C8 109.70(15) . . ? C5 C6 C8 108.86(15) . . ? O1 C6 C7 109.51(14) . . ? C5 C6 C7 109.40(14) . . ? C8 C6 C7 110.71(16) . . ? C3 C4 C5 118.99(17) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C1 C2 C3 118.38(16) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 119.95(16) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? 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 . . ? 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 1.8365(15) 3_666 ? Ni1 O1 1.8365(15) . ? Ni1 N1 1.8709(14) . ? Ni1 N1 1.8709(14) 3_666 ? O1 C6 1.413(2) . ? N1 C5 1.349(2) . ? N1 C1 1.350(2) . ? C1 C2 1.380(2) . ? C1 H1 0.9500 . ? C5 C4 1.393(2) . ? C5 C6 1.517(2) . ? C6 C8 1.531(3) . ? C6 C7 1.536(3) . ? C4 C3 1.383(3) . ? C4 H4 0.9500 . ? C2 C3 1.389(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 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 N1 Ni1 O1 C6 17.81(11) . . . . ? N1 Ni1 O1 C6 -162.19(11) 3_666 . . . ? O1 Ni1 N1 C5 168.83(12) 3_666 . . . ? O1 Ni1 N1 C5 -11.17(12) . . . . ? O1 Ni1 N1 C1 -9.93(14) 3_666 . . . ? O1 Ni1 N1 C1 170.07(14) . . . . ? C5 N1 C1 C2 -1.2(2) . . . . ? Ni1 N1 C1 C2 177.47(13) . . . . ? C1 N1 C5 C4 2.1(2) . . . . ? Ni1 N1 C5 C4 -176.71(13) . . . . ? C1 N1 C5 C6 -178.53(15) . . . . ? Ni1 N1 C5 C6 2.62(18) . . . . ? Ni1 O1 C6 C5 -19.66(17) . . . . ? Ni1 O1 C6 C8 99.22(15) . . . . ? Ni1 O1 C6 C7 -139.08(12) . . . . ? N1 C5 C6 O1 10.7(2) . . . . ? C4 C5 C6 O1 -170.01(16) . . . . ? N1 C5 C6 C8 -108.70(17) . . . . ? C4 C5 C6 C8 70.6(2) . . . . ? N1 C5 C6 C7 130.19(16) . . . . ? C4 C5 C6 C7 -50.5(2) . . . . ? N1 C5 C4 C3 -1.3(3) . . . . ? C6 C5 C4 C3 179.41(17) . . . . ? N1 C1 C2 C3 -0.5(3) . . . . ? C5 C4 C3 C2 -0.4(3) . . . . ? C1 C2 C3 C4 1.3(3) . . . . ?