Rh(iii)-catalyzed heteroannular-selective heteroarylation of biaryls: facile access to heteroacenes with sulfur-embedded 5-7 ring topology.
He, Zhanhui; Yang, Li; Zhou, Menghang; Zhong, Yue; Liu, Zheng; Zhang, Ziao; Xia, Feiyang; Deng, Xuezhe; Yan, Shuang; Xu, Cheng; Zhang, Cheng; Yin, Guodong; Chemical science 17 (2026) 4594–4600; doi:10.1039/d5sc08209a

data_1576770
_publ_section_title
;
 Rh(iii)-catalyzed heteroannular-selective heteroarylation of biaryls:
 facile access to heteroacenes with sulfur-embedded 5-7 ring topology.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              4594
_journal_page_last               4600
_journal_paper_doi               10.1039/d5sc08209a
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C20 H12 S'
_chemical_formula_sum            'C20 H12 S'
_chemical_formula_weight         284.36
_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_date             2025-02-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-21 deposited with the CCDC.	2026-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2323(2)
_cell_length_b                   8.9668(4)
_cell_length_c                   29.1269(10)
_cell_measurement_reflns_used    2839
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.6690
_cell_measurement_theta_min      5.1550
_cell_volume                     1366.55(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_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    -25.00  31.00   0.50    0.20    --  -42.11  18.00  14.00  112
  2  \w    -61.00 -13.00   0.50    0.20    --  -42.11 124.00  79.00   96
  3  \w    -95.00 -70.00   0.50    0.42    --  -94.45  18.00  14.00   50
  4  \w    -55.00  23.00   0.50    0.20    --  -42.11  32.00 -90.00  156
  5  \w     79.00 104.00   0.50    0.20    --   43.99  32.00 -60.00   50
  6  \w     66.00  94.00   0.50    0.20    --   43.99  18.00  14.00   56
  7  \w    125.00 169.00   0.50    0.42    --   96.32  18.00  14.00   88
  8  \w     86.00 111.00   0.50    0.42    --   96.32-109.00  82.00   50
  9  \w     74.00 110.00   0.50    0.42    --   96.32 -33.00  90.00   72
 10  \w     75.00 102.00   0.50    0.42    --   96.32  18.00  14.00   54
 11  \w     71.00 123.00   0.50    0.42    --   96.32 124.00  79.00  104
 12  \w    122.00 164.00   0.50    0.42    --   96.32 109.00 178.00   84
 13  \w     48.00  73.00   0.50    0.42    --   96.32-124.00   0.00   50
 14  \w    -83.00 -57.00   0.50    0.20    --  -42.11-146.00-165.00   52
 15  \w    -83.00 -58.00   0.50    0.20    --  -42.11 -18.00-153.00   50
 16  \w    -92.00 -22.00   0.50    0.42    --  -94.45  96.00-120.00  140
 17  \w    -86.00 -26.00   0.50    0.42    --  -94.45  96.00 -90.00  120
 18  \w     77.00 102.00   0.50    0.20    --   43.99 146.00-115.00   50
 19  \w    111.00 158.00   0.50    0.42    --   96.32 146.00-115.00   94
 20  \w     63.00  90.00   0.50    0.42    --   96.32-117.00-180.00   54
 21  \w    -26.00  -1.00   0.50    0.20    --  -42.11 109.00 178.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0256453000
_diffrn_orient_matrix_UB_12      0.1311015000
_diffrn_orient_matrix_UB_13      0.0338850000
_diffrn_orient_matrix_UB_21      -0.0656177000
_diffrn_orient_matrix_UB_22      0.1101955000
_diffrn_orient_matrix_UB_23      -0.0388092000
_diffrn_orient_matrix_UB_31      -0.2859246000
_diffrn_orient_matrix_UB_32      -0.0135173000
_diffrn_orient_matrix_UB_33      0.0119428000
_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            4479
_diffrn_reflns_point_group_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.949
_diffrn_reflns_theta_min         5.161
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 584 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0860P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.464
_reflns_Friedel_fraction_full    0.693
_reflns_Friedel_fraction_max     0.691
_reflns_number_gt                1975
_reflns_number_total             2178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08209a2.cif
_cod_data_source_block           ygd-2
_cod_database_code               1576770
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.755
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              2470
_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 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.550