Nickel/N-Heterocyclic Carbene Complex-Catalyzed Enantioselective Redox-Neutral Coupling of Benzyl Alcohols and Alkynes to Allylic Alcohols
Cai, Yuan; Zhang, Jia-Wen; Li, Feng; Liu, Jia-Ming; Shi, Shi-Liang; ACS Catalysis 9 (2018) 1–; doi:10.1021/acscatal.8b04198

data_4515483
_publ_section_title
;
 Nickel/N-Heterocyclic Carbene Complex-Catalyzed Enantioselective
 Redox-Neutral Coupling of Benzyl Alcohols and Alkynes to Allylic Alcohols
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              1
_journal_paper_doi               10.1021/acscatal.8b04198
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C71 H72 N2 Ni'
_chemical_formula_weight         1012.01
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9159(5)
_cell_length_b                   18.7470(7)
_cell_length_c                   20.4012(9)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.053
_cell_measurement_theta_min      4.546
_cell_volume                     5704.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_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  0.0495
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30067
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.996
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 3168 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.006(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     673
_refine_ls_number_reflns         10567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0381P)^2^+0.0621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                8582
_reflns_number_total             10567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04198_si_002.cif
_cod_data_source_block           mo_d8v17456_0m
_cod_database_code               4515483
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.955
_shelxl_version_number           2013-4
_shelx_res_checksum              9536
_shelx_hkl_checksum              35343