Synthesis of dibenzoarsole derivatives from biarylborates <i>via</i> the twofold formation of C-As bonds using arsenium dication equivalents.
Nishimura, Kazutoshi; Iwamoto, Hiroki; Nishii, Yuji; Hirano, Koji; Chemical science 16 (2025) 21433–21439; doi:10.1039/d5sc05528h

data_1576020
_publ_section_title
;
 Synthesis of dibenzoarsole derivatives from biarylborates <i>via</i> the
 twofold formation of C-As bonds using arsenium dication equivalents.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              21433
_journal_page_last               21439
_journal_paper_doi               10.1039/d5sc05528h
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C19 H11 As S'
_chemical_formula_sum            'C19 H11 As S'
_chemical_formula_weight         346.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-31 deposited with the CCDC.	2025-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                70.661(6)
_cell_angle_beta                 83.531(6)
_cell_angle_gamma                83.032(6)
_cell_formula_units_Z            2
_cell_length_a                   7.6593(5)
_cell_length_b                   8.7731(6)
_cell_length_c                   11.3505(8)
_cell_measurement_reflns_used    4302
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.9500
_cell_measurement_theta_min      4.1190
_cell_volume                     712.21(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
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_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.941
_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    -54.00  -9.00   0.50    0.37    --  -42.55  98.00-162.00   90
  2  \w     -6.00  27.00   0.50    0.37    --  -42.55  98.00-162.00   66
  3  \w    -17.00  74.00   0.50    0.37    --   42.55 -98.00  90.00  182
  4  \w    127.00 153.00   0.50    1.48    --   96.50  98.00-162.00   52
  5  \w     89.00 115.00   0.50    1.48    --   96.50  98.00-162.00   52
  6  \w   -105.00 -61.00   0.50    1.48    -- -111.75  98.00-162.00   88
  7  \w    -36.00   2.00   0.50    0.37    --   42.55 -19.00  90.00   76
  8  \w     51.00  92.00   0.50    0.37    --   42.55-125.00 -60.00   82
  9  \w    -35.00  20.00   0.50    0.37    --   42.55 -37.00   0.00  110
 10  \w     60.00  85.00   0.50    0.37    --   42.55-125.00 120.00   50
 11  \w    -29.00   4.00   0.50    0.37    --   42.55 -19.00-150.00   66
 12  \w    -26.00  42.00   0.50    0.37    --   42.55 -57.00 -60.00  136
 13  \w     75.00 101.00   0.50    1.48    --   96.50  45.00 -60.00   52
 14  \w    102.00 156.00   0.50    1.48    --   96.50  45.00 150.00  108
 15  \w     22.00  47.00   0.50    1.48    --   96.50 -61.00 -90.00   50
 16  \w     23.00  50.00   0.50    1.48    --   96.50 -61.00-180.00   54
 17  \w     22.00  50.00   0.50    1.48    --   96.50 -61.00  30.00   56
 18  \w     62.00 102.00   0.50    1.48    --   96.50 -98.00  90.00   80
 19  \w    110.00 155.00   0.50    1.48    --   96.50  45.00 -60.00   90
 20  \w     83.00 108.00   0.50    1.48    --   96.50  45.00-180.00   50
 21  \w   -109.00 -54.00   0.50    1.48    -- -111.75 125.00 -30.00  110
 22  \w   -125.00 -73.00   0.50    1.48    -- -111.75-125.00 120.00  104
 23  \w   -103.00 -78.00   0.50    1.48    -- -111.75 125.00   0.00   50
 24  \w   -165.00-134.00   0.50    1.48    -- -111.75-125.00 120.00   62
 25  \w   -120.00 -37.00   0.50    1.48    -- -111.75 136.00-100.84  166
 26  \w   -164.00-136.00   0.50    1.48    -- -111.75 -77.00-180.00   56
 27  \w   -145.00 -88.00   0.50    1.48    -- -111.75 -61.00  30.00  114
 28  \w   -176.00-149.00   0.50    1.48    -- -111.75 -61.00  30.00   54
 29  \w   -125.00 -39.00   0.50    1.48    -- -111.75 143.00  39.85  172
 30  \w   -105.00 -40.00   0.50    1.48    -- -111.75 125.00-150.00  130
 31  \w   -166.00 -92.00   0.50    1.48    -- -111.75 -94.00 150.00  148
 32  \w    -85.00 -48.00   0.50    1.48    -- -111.75  61.00-120.00   74
 33  \w    -68.00 -42.00   0.50    1.48    -- -111.75  77.00 150.00   52
 34  \w    -89.00 -41.00   0.50    1.48    -- -111.75 125.00 -60.00   96
 35  \w   -125.00 -75.00   0.50    1.48    -- -111.75  77.00 150.00  100
 36  \w    -62.00 -36.00   0.50    1.48    -- -111.75  45.00-180.00   52
 37  \w   -142.00 -95.00   0.50    1.48    -- -111.75-125.00-120.00   94
 38  \w   -123.00 -83.00   0.50    1.48    -- -111.75 -77.00-180.00   80
 39  \w   -159.00 -99.00   0.50    1.48    -- -111.75 -98.00  90.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1001731000
_diffrn_orient_matrix_UB_12      0.1212965000
_diffrn_orient_matrix_UB_13      -0.1095130000
_diffrn_orient_matrix_UB_21      0.1562460000
_diffrn_orient_matrix_UB_22      -0.0254158000
_diffrn_orient_matrix_UB_23      0.0809435000
_diffrn_orient_matrix_UB_31      0.0828259000
_diffrn_orient_matrix_UB_32      -0.1398392000
_diffrn_orient_matrix_UB_33      -0.0476485000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6646
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.712
_diffrn_reflns_theta_min         4.140
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.486
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.615
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.046
_refine_diff_density_max         1.415
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0697
_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^)+(0.1357P)^2^+0.4966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1810
_refine_ls_wR_factor_ref         0.1901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2483
_reflns_number_total             2821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05528h2.cif
_cod_data_source_block           nishimura_231014_autored
_cod_depositor_comments          'Adding full bibliography for 1576020.cif.'
_cod_database_code               1576020
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C38 H22 As2 S2'
_shelx_estimated_absorpt_t_max   0.807
_shelx_estimated_absorpt_t_min   0.593
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C4(H4), C5(H5), C16(H16), C18(H18), C17(H17), C7(H7),
 C14(H14), C6(H6), C15(H15)
;
_shelx_res_checksum              82918
_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 1.978
_oxdiff_exptl_absorpt_empirical_full_min 0.607