Nickel-catalyzed stereospecific reductive cross-coupling of vinyl chlorosilanes with axially chiral biaryl electrophiles.
Yin, Tiantian; Sui, Shiyuan; Li, Shuqi; Chang, Junbiao; Bai, Dachang; Chemical communications (Cambridge, England) 60 (2024) 14204–14207; doi:10.1039/d4cc04293j

data_7133970
_publ_section_title
;
 Nickel-catalyzed stereospecific reductive cross-coupling of vinyl
 chlorosilanes with axially chiral biaryl electrophiles.
;
_journal_issue                   96
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14204
_journal_page_last               14207
_journal_paper_doi               10.1039/d4cc04293j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C34 H26 Si'
_chemical_formula_sum            'C34 H26 Si'
_chemical_formula_weight         462.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-09-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-09-30 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.4420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5996(2)
_cell_length_b                   9.42640(10)
_cell_length_c                   18.8989(2)
_cell_measurement_reflns_used    22415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3350
_cell_measurement_theta_min      3.6700
_cell_volume                     2593.09(5)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1162
_diffrn_reflns_av_unetI/netI     0.0603
_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       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43685
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.588
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         3.691
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.66094
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 3559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         9145
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0583
_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^)+(0.1079P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                8453
_reflns_number_total             9145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04293j2.cif
_cod_data_source_block           2_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133970.cif.
;
_cod_database_code               7133970
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.767
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C50(H50), C8(H8), C51(H51), C26(H26), C9(H9), C36(H36),
 C37(H37), C42(H42), C10(H10), C19(H19), C12(H12), C2(H2), C33(H33), C13(H13),
 C56(H56), C67(H67), C53(H53), C61(H61), C62(H62), C6(H6), C40(H40), C3(H3),
 C60(H60), C38(H38), C64(H64), C47(H47), C46(H46), C22(H22), C66(H66), C5(H5),
 C20(H20), C55(H55), C43(H43), C44(H44), C11(H11), C4(H4), C45(H45), C21(H21),
 C27(H27), C39(H39), C54(H54), C28(H28), C65(H65), C32(H32), C31(H31), C30(H30)
2.b X=CH2 refined with riding coordinates:
 C14(H14A,H14B), C48(H48A,H48B)
;
_shelx_res_checksum              18876
_olex2_submission_special_instructions 'No special instructions were received'