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_1576774
_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 O4 S2'
_chemical_formula_sum            'C20 H12 O4 S2'
_chemical_formula_weight         380.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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            8
_cell_length_a                   8.02320(10)
_cell_length_b                   16.8258(3)
_cell_length_c                   25.0537(4)
_cell_measurement_reflns_used    7017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.2220
_cell_measurement_theta_min      3.5320
_cell_volume                     3382.17(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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_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    -14.00  57.00   0.50    1.27    --   44.11 -32.00 -30.00  142
  2  \w     30.00  55.00   0.50    5.10    --   96.32-117.00 -60.00   50
  3  \w     65.00  91.00   0.50    5.10    --   96.32-117.00 -60.00   52
  4  \w     72.00 111.00   0.50    5.10    --   96.32 -26.00-108.00   78
  5  \w     77.00 102.00   0.50    5.10    --   96.32-135.00-149.00   50
  6  \w     -4.00  39.00   0.50    1.27    --   44.11 -26.00-108.00   86
  7  \w     81.00 114.00   0.50    5.10    --   96.32  25.00-180.00   66
  8  \w    138.00 167.00   0.50    5.10    --   96.32  25.00-180.00   58
  9  \w     81.00 170.00   0.50    5.10    --   96.32  97.00-152.00  178
 10  \w     53.00  79.00   0.50    1.27    --   44.11-134.00  30.00   52
 11  \w     51.00 123.00   0.50    5.10    --   96.32 -77.00  30.00  144
 12  \w     73.00  99.00   0.50    5.10    --   96.32 -97.00  99.00   52
 13  \w     19.00  73.00   0.50    1.27    --   44.11 -97.00  99.00  108
 14  \w     79.00 104.00   0.50    1.27    --   44.11  26.00  54.00   50
 15  \w     95.00 138.00   0.50    5.10    --   96.32  26.00  54.00   86
 16  \w     65.00 108.00   0.50    1.27    --   44.11 134.00  96.00   86
 17  \w     89.00 114.00   0.50    5.10    --   96.32 134.00  96.00   50
 18  \w    -40.00 -15.00   0.50    1.27    --  -42.24 134.00  96.00   50
 19  \w   -111.00 -37.00   0.50    5.10    --  -94.45 117.00   0.00  148
 20  \w   -111.00 -85.00   0.50    1.27    --  -42.24 -26.00-108.00   52
 21  \w    -46.00 -21.00   0.50    1.27    --  -42.24  97.00-152.00   50
 22  \w   -146.00-121.00   0.50    5.10    --  -94.45 -26.00-108.00   50
 23  \w   -100.00 -74.00   0.50    1.27    --  -42.24-138.00 -30.00   52
 24  \w   -133.00-108.00   0.50    5.10    --  -94.45-134.00  30.00   50
 25  \w    -88.00 -61.00   0.50    1.27    --  -42.24-138.00-180.00   54
 26  \w   -162.00 -79.00   0.50    5.10    --  -94.45 -42.00-180.00  166
;
_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      -0.0619699000
_diffrn_orient_matrix_UB_12      -0.0761498000
_diffrn_orient_matrix_UB_13      -0.0277817000
_diffrn_orient_matrix_UB_21      0.0321594000
_diffrn_orient_matrix_UB_22      0.0384178000
_diffrn_orient_matrix_UB_23      -0.0548551000
_diffrn_orient_matrix_UB_31      0.1788575000
_diffrn_orient_matrix_UB_32      -0.0333119000
_diffrn_orient_matrix_UB_33      0.0002101000
_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  0.0439
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12149
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.323
_diffrn_reflns_theta_min         3.528
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42100
_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    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0655
_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^)+(0.0867P)^2^+4.0966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2731
_reflns_number_total             3077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08209a2.cif
_cod_data_source_block           ygd-4
_cod_database_code               1576774
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.656
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_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 2.017
_oxdiff_exptl_absorpt_empirical_full_min 0.329