#------------------------------------------------------------------------------
#$Date: 2022-01-03 22:50:25 +0200 (Mon, 03 Jan 2022) $
#$Revision: 271721 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/92/4519225.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4519225
loop_
_publ_author_name
'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'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     17.00  59.00   1.00    1.00    --   40.98 -37.00  60.00   42
  2  ω     37.00  82.00   1.00    1.00    --   40.98-125.00  60.00   45
  3  ω     45.00 123.00   1.00    1.00    --  107.58 -45.00  30.00   78
  4  ω     75.00 114.00   1.00    1.00    --  107.58-125.00  60.00   39
  5  ω     39.00  66.00   1.00    1.00    --  107.58-125.00  60.00   27
  6  ω     32.00 117.00   1.00    1.00    --  107.58 -77.00  30.00   85
  7  ω     79.00 125.00   1.00    1.00    --  107.58 -61.00-120.00   46
  8  ω     78.00 119.00   1.00    1.00    --  107.58-125.00-150.00   41
  9  ω     61.00 108.00   1.00    1.00    --  107.58 -94.00-120.00   47
 10  ω     41.00 178.00   1.00    1.00    --  107.58   0.00-180.00  137
 11  ω     89.00 165.00   1.00    1.00    --  107.58  45.00-150.00   76
 12  ω     36.00  76.00   1.00    1.00    --  107.58-125.00-150.00   40
 13  ω     25.00  51.00   1.00    1.00    --  107.58 -94.00-120.00   26
 14  ω     40.00 129.00   1.00    1.00    --  107.58 -45.00-180.00   89
 15  ω     26.00  86.00   1.00    1.00    --   40.98-125.00 -90.00   60
 16  ω   -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       'ω 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/[σ²(Fo²)+(0.0904P)²] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.44627(2) 0.31607(5) 0.54560(2) 0.01544(19) Uani 1 1 d . . . . .
C8 C 0.2934(5) 0.2866(9) 0.4360(4) 0.0173(10) Uani 1 1 d . . . . .
C4 C 0.2942(4) 0.9340(9) 0.6858(3) 0.0218(10) Uani 1 1 d . . . . .
H4 H 0.313881 1.036061 0.738065 0.026 Uiso 1 1 calc R . . . .
C7 C 0.2049(4) 0.4512(9) 0.4486(3) 0.0173(9) Uani 1 1 d . . . . .
C6 C 0.3415(4) 0.6013(10) 0.5895(3) 0.0168(9) Uani 1 1 d . . . . .
C1 C 0.2318(4) 0.6232(11) 0.5291(3) 0.0188(9) Uani 1 1 d . . . . .
C10 C 0.1678(4) 0.1054(11) 0.3012(4) 0.0221(10) Uani 1 1 d . . . . .
H10 H 0.155680 -0.007285 0.251844 0.027 Uiso 1 1 calc R . . . .
C2 C 0.1550(5) 0.8070(9) 0.5481(4) 0.0229(12) Uani 1 1 d . . . . .
H2 H 0.082296 0.825986 0.508641 0.028 Uiso 1 1 calc R . . . .
C12 C 0.0982(4) 0.4373(9) 0.3864(3) 0.0214(10) Uani 1 1 d . . . . .
H12 H 0.038719 0.544359 0.393620 0.026 Uiso 1 1 calc R . . . .
C9 C 0.2742(4) 0.1154(10) 0.3632(3) 0.0199(9) Uani 1 1 d . . . . .
H9 H 0.333191 0.006839 0.356070 0.024 Uiso 1 1 calc R . . . .
C5 C 0.3721(4) 0.7532(12) 0.6676(4) 0.0181(9) Uani 1 1 d . . . . .
H5 H 0.444272 0.734674 0.707677 0.022 Uiso 1 1 calc R . . . .
C3 C 0.1870(4) 0.9589(10) 0.6248(3) 0.0227(10) Uani 1 1 d . . . . .
H3 H 0.135586 1.081279 0.636100 0.027 Uiso 1 1 calc R . . . .
C11 C 0.0786(4) 0.2655(13) 0.3131(4) 0.0246(10) Uani 1 1 d . . . . .
H11 H 0.006449 0.257372 0.272248 0.030 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.0562 5.8946 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 Sb1 Sb1 94.57(13) . 3_666 ?
C8 Sb1 C6 80.47(19) . . ?
C6 Sb1 Sb1 91.91(12) . 3_666 ?
C7 C8 Sb1 112.3(4) . . ?
C9 C8 Sb1 126.7(4) . . ?
C9 C8 C7 120.8(5) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(5) . . ?
C8 C7 C1 117.3(4) . . ?
C12 C7 C8 118.2(4) . . ?
C12 C7 C1 124.4(4) . . ?
C1 C6 Sb1 112.3(4) . . ?
C5 C6 Sb1 126.9(3) . . ?
C5 C6 C1 120.8(4) . . ?
C6 C1 C7 117.5(4) . . ?
C2 C1 C7 123.9(5) . . ?
C2 C1 C6 118.5(5) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(5) . . ?
C11 C10 H10 120.1 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 120.0 . . ?
C7 C12 H12 119.5 . . ?
C7 C12 C11 121.1(4) . . ?
C11 C12 H12 119.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 H9 119.8 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 H3 119.2 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Sb1 2.8371(6) 3_666 ?
Sb1 C8 2.148(5) . ?
Sb1 C6 2.149(5) . ?
C8 C7 1.410(7) . ?
C8 C9 1.387(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(7) . ?
C4 C3 1.389(7) . ?
C7 C1 1.478(7) . ?
C7 C12 1.389(7) . ?
C6 C1 1.406(7) . ?
C6 C5 1.389(8) . ?
C1 C2 1.404(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.382(7) . ?
C10 C11 1.399(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.395(8) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
