Deciphering the Mechanism of the Nickel-Catalyzed Hydroalkoxylation Reaction: A Combined Experimental and Computational Study
Mifleur, Alexis; Mérel, Delphine S.; Mortreux, André; Suisse, Isabelle; Capet, Frédéric; Trivelli, Xavier; Sauthier, Mathieu; Macgregor, Stuart A.; ACS Catalysis 7 (2017) 6915–; doi:10.1021/acscatal.7b00616

data_4514195
_publ_section_title
;
 Deciphering the Mechanism of the Nickel-Catalyzed Hydroalkoxylation
 Reaction: A Combined Experimental and Computational Study
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              6915
_journal_paper_doi               10.1021/acscatal.7b00616
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C32 H35 Cl Ni P2'
_chemical_formula_sum            'C32 H35 Cl Ni P2'
_chemical_formula_weight         575.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_cell_angle_alpha                100.947(2)
_cell_angle_beta                 102.623(2)
_cell_angle_gamma                105.014(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3622(4)
_cell_length_b                   11.0841(3)
_cell_length_c                   13.1883(5)
_cell_measurement_reflns_used    7473
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.29
_cell_volume                     1377.98(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31221
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.639
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.937
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0629 before and 0.0498 after correction.
The Ratio of minimum to maximum transmission is 0.9309.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       irregular
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0392P)^2^+1.5097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4542
_reflns_number_total             5628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00616_si_003.cif
_cod_data_source_block           mo_am496d_0m
_cod_depositor_comments
'Adding full bibliography for 4514194--4514195.cif.'
_cod_database_code               4514195
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C15(H15A,H15B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C28(H28), C12(H12), C5(H5), C3(H3), C20(H20), C24(H24),
 C8(H8), C27(H27), C22(H22), C25(H25), C4(H4), C21(H21), C11(H11), C10(H10),
 C26(H26), C18(H18), C9(H9), C19(H19)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'