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_1576771
_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         '2(C22 H12 S2)'
_chemical_formula_sum            'C44 H24 S4'
_chemical_formula_weight         680.87
_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             2025-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
;
_audit_update_record
;
2025-07-24 deposited with the CCDC.	2026-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                97.109(2)
_cell_angle_beta                 101.458(2)
_cell_angle_gamma                95.919(2)
_cell_formula_units_Z            1
_cell_length_a                   7.9692(3)
_cell_length_b                   9.1737(3)
_cell_length_c                   11.3045(4)
_cell_measurement_reflns_used    3415
_cell_measurement_temperature    297
_cell_measurement_theta_max      66.225
_cell_measurement_theta_min      4.035
_cell_volume                     796.78(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      297
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
'C19a  C     1.01781  0.28261  0.50113 -31.00000  0.09187'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8332
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.671
_diffrn_reflns_theta_max         66.671
_diffrn_reflns_theta_min         4.034
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.993
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1556 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.4449.
The \l/2 correction factor is Not present.
;
_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    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.064
_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     217
_refine_ls_number_reflns         2787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0975P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1465
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2256
_reflns_number_total             2787
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08209a2.cif
_cod_data_source_block           1025liuzheng2_0m
_cod_database_code               1576771
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.662
_shelx_estimated_absorpt_t_min   0.586
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C19(H19),
 C20(H20), C21(H21), C22(H22)
;
_shelx_res_checksum              84753
_olex2_submission_special_instructions 'No special instructions were received'