Nickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes
Zhang, Dejiang; Tang, Ting; Zhang, Zhao; Le, Liyuan; Xu, Zhi; Lu, Hao; Tong, Zhou; Zeng, Dishu; Wong, Wai-Yeung; Yin, Shuang-Feng; Ghaderi, Arash; Kambe, Nobuaki; Qiu, Renhua; ACS Catalysis  (2021) 854–867; doi:10.1021/acscatal.1c04533

data_4519225
_publ_section_title
;
 Nickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic
 Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              854
_journal_page_last               867
_journal_paper_doi               10.1021/acscatal.1c04533
_journal_year                    2021
_chemical_formula_moiety         'C24 H16 Sb2'
_chemical_formula_sum            'C24 H16 Sb2'
_chemical_formula_weight         547.87
_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     dual
_audit_creation_date             2019-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.680(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9115(7)
_cell_length_b                   5.2479(3)
_cell_length_c                   14.9482(8)
_cell_measurement_reflns_used    3616
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6790
_cell_measurement_theta_min      4.2530
_cell_volume                     907.91(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     17.00  59.00   1.00    1.00    --   40.98 -37.00  60.00   42
  2  \w     37.00  82.00   1.00    1.00    --   40.98-125.00  60.00   45
  3  \w     45.00 123.00   1.00    1.00    --  107.58 -45.00  30.00   78
  4  \w     75.00 114.00   1.00    1.00    --  107.58-125.00  60.00   39
  5  \w     39.00  66.00   1.00    1.00    --  107.58-125.00  60.00   27
  6  \w     32.00 117.00   1.00    1.00    --  107.58 -77.00  30.00   85
  7  \w     79.00 125.00   1.00    1.00    --  107.58 -61.00-120.00   46
  8  \w     78.00 119.00   1.00    1.00    --  107.58-125.00-150.00   41
  9  \w     61.00 108.00   1.00    1.00    --  107.58 -94.00-120.00   47
 10  \w     41.00 178.00   1.00    1.00    --  107.58   0.00-180.00  137
 11  \w     89.00 165.00   1.00    1.00    --  107.58  45.00-150.00   76
 12  \w     36.00  76.00   1.00    1.00    --  107.58-125.00-150.00   40
 13  \w     25.00  51.00   1.00    1.00    --  107.58 -94.00-120.00   26
 14  \w     40.00 129.00   1.00    1.00    --  107.58 -45.00-180.00   89
 15  \w     26.00  86.00   1.00    1.00    --   40.98-125.00 -90.00   60
 16  \w   -129.00  47.00   1.00    1.00    --  -40.98   0.00 150.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0542944000
_diffrn_orient_matrix_UB_12      0.0133006000
_diffrn_orient_matrix_UB_13      0.1042233000
_diffrn_orient_matrix_UB_21      0.1215088000
_diffrn_orient_matrix_UB_22      0.0008789000
_diffrn_orient_matrix_UB_23      -0.0190534000
_diffrn_orient_matrix_UB_31      -0.0028760000
_diffrn_orient_matrix_UB_32      0.2933928000
_diffrn_orient_matrix_UB_33      -0.0045606000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5306
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.788
_diffrn_reflns_theta_min         4.285
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    23.608
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.462
_refine_diff_density_min         -1.261
_refine_diff_density_rms         0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0904P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1696
_reflns_number_total             1816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c04533_si_002.cif
_cod_data_source_block           651
_cod_database_code               4519225
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.225
_shelx_estimated_absorpt_t_min   0.181
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C2(H2), C12(H12), C9(H9), C5(H5), C3(H3), C11(H11)
;
_shelx_res_checksum              38845
_shelx_hkl_checksum              27459
_olex2_date_sample_data_collection 2019-09-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 14.320
_oxdiff_exptl_absorpt_empirical_full_min 0.355