Synthesis of 1H-isothiochromenes by regioselective C–C and C–S bond formation of enaminothiones with alkynes under rhodium catalysis
Yan, Kelu; Sun, Yuhang; Wen, Jiangwei; Li, Qiuyun; Yu, Xinming; Shang, Wenxu; Wang, Xiu; Chemical Communications 61 (2025) 7482–7485; doi:10.1039/D5CC01269D

data_7134412
_publ_section_title
;
 Synthesis of 1H-isothiochromenes by regioselective C--C and C--S bond
 formation of enaminothiones with alkynes under rhodium catalysis
;
_journal_issue                   41
_journal_name_full               'Chemical Communications'
_journal_page_first              7482
_journal_page_last               7485
_journal_paper_doi               10.1039/D5CC01269D
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C23 H16 O S'
_chemical_formula_sum            'C23 H16 O S'
_chemical_formula_weight         340.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-16 deposited with the CCDC.	2025-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.183(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7462(15)
_cell_length_b                   9.1384(10)
_cell_length_c                   15.0589(17)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.61
_cell_volume                     1746.9(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_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  0.0262
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28047
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.677
_diffrn_reflns_theta_min         2.194
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0909 before and 0.0470 after correction. The Ratio of minimum to maximum transmission is 0.8963. The \l/2 correction factor is Not present.'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       blcok
_exptl_crystal_F_000             712
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.2943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4254
_reflns_number_total             5329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01269d2.cif
_cod_data_source_block           231012_y1_0m
_cod_depositor_comments          'Adding full bibliography for 7134412.cif.'
_cod_database_code               7134412
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(S1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C13(H13), C6(H6), C22(H22), C20(H20), C10(H10), C21(H21), C8(H8),
 C2(H2), C14(H14), C17(H17), C7(H7), C1(H1), C15(H15), C9(H9), C16(H16)
;
_shelx_res_checksum              42296
_shelx_hkl_checksum              36414
_olex2_submission_special_instructions 'No special instructions were received'