Role of High-Spin Species and Pendant Amines in Electrocatalytic Alcohol Oxidation by a Nickel Phosphine Complex
Gunasekara, Thilina; Tong, Yicheng; Speelman, Amy L.; Erickson, Jeremy D.; Appel, Aaron M.; Hall, Michael B.; Wiedner, Eric S.; ACS Catalysis  (2022) 2729–2740; doi:10.1021/acscatal.1c05509

data_4519334
_publ_section_title
;
 Role of High-Spin Species and Pendant Amines in Electrocatalytic Alcohol
 Oxidation by a Nickel Phosphine Complex
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2729
_journal_page_last               2740
_journal_paper_doi               10.1021/acscatal.1c05509
_journal_year                    2022
_chemical_formula_moiety         'C20 H45 N2 Ni O P2, B F4'
_chemical_formula_sum            'C20 H45 B F4 N2 Ni O P2'
_chemical_formula_weight         537.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                100.077(3)
_cell_angle_beta                 105.481(3)
_cell_angle_gamma                107.418(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7943(9)
_cell_length_b                   10.8646(9)
_cell_length_c                   13.9683(11)
_cell_measurement_reflns_used    9499
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.499
_cell_measurement_theta_min      2.808
_cell_volume                     1313.2(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            70506
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_min         2.469
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.903
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1111 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.9189. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.181
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         7986
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0222
_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^)+(0.0235P)^2^+0.5320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0577
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7654
_reflns_number_total             7986
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05509_si_003.cif
_cod_data_source_block           162_3_0m_a
_cod_original_cell_volume        1313.22(19)
_cod_database_code               4519334
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.746
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 B1-F1 \\sim B2-F1
 with sigma of 0.02
 B1-F4 \\sim B2-F6
 with sigma of 0.02
 B1-F3 \\sim B2-F5
 with sigma of 0.02
 B1-F2 \\sim B2-F2
 with sigma of 0.02
 F1-F4 \\sim F1-F6
 with sigma of 0.04
 F1-F3 \\sim F1-F5
 with sigma of 0.04
 F4-F3 \\sim F6-F5
 with sigma of 0.04
 F4-F2 \\sim F6-F2
 with sigma of 0.04
 F3-F2 \\sim F5-F2
 with sigma of 0.04
3. Others
 Fixed Sof: F3(0.6666) F4(0.6666) B1(0.6666) F5(0.3334) F6(0.3334) B2(0.3334)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
4.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C),
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,
 H20B,H20C)
;
_shelx_res_checksum              3445
_shelx_hkl_checksum              88497
_olex2_submission_special_instructions 'No special instructions were received'