Rh(III)-catalyzed oxidative C-H cross-coupling between indoles and thiophenes/furanes.
Wang, Yuhao; Li, Li; Zhao, Quansheng; Gao, Pengming; Guo, Kaiyue; Zhang, Jitan; Wu, Jiaping; Chemical communications (Cambridge, England) 61 (2025) 17213–17216; doi:10.1039/d5cc04882f

data_1575842
_publ_section_title
;
 Rh(III)-catalyzed oxidative C-H cross-coupling between indoles and
 thiophenes/furanes.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17213
_journal_page_last               17216
_journal_paper_doi               10.1039/d5cc04882f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C22 H16 N2 S'
_chemical_formula_sum            'C22 H16 N2 S'
_chemical_formula_weight         340.43
_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             2020-12-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-07-22 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                89.432(2)
_cell_angle_beta                 81.031(2)
_cell_angle_gamma                69.392(2)
_cell_formula_units_Z            4
_cell_length_a                   10.2433(6)
_cell_length_b                   11.4047(7)
_cell_length_c                   16.4484(9)
_cell_measurement_reflns_used    9790
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      3.35
_cell_volume                     1774.48(18)
_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_temperature      300.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            42316
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         3.030
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         8102
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0648P)^2^+0.9353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1553
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6151
_reflns_number_total             8102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04882f2.cif
_cod_data_source_block           mo_20201231c_0m
_cod_depositor_comments          'Adding full bibliography for 1575842.cif.'
_cod_database_code               1575842
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C25, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C16(H16),
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C32(H32), C33(H33), C34(H34), C38(H38), C41(H41), C42(H42),
 C43(H43), C44(H44)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              18202
_olex2_submission_special_instructions 'No special instructions were received'