Heterogeneous visible-light promoted dehydrogenative [4 + 2] annulation of benzothioamides and alkynes under aerobic conditions
Guo, Yanmin; Chang, Rong; Fu, Zhen; Zhou, Cong-Ying; Guo, Zhen; Green Chemistry 25 (2023) 5206–5212; doi:10.1039/D3GC01329D

data_7246832
_publ_section_title
;
 Heterogeneous visible-light promoted dehydrogenative [4 + 2] annulation
 of benzothioamides and alkynes under aerobic conditions
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              5206
_journal_page_last               5212
_journal_paper_doi               10.1039/D3GC01329D
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C22 H16 Cl N S'
_chemical_formula_sum            'C22 H16 Cl N S'
_chemical_formula_weight         361.87
_chemical_melting_point          107.2
_chemical_name_systematic
(Z)-5-chloro-3-methyl-N,4-diphenyl-1H-isothiochromen-1-imine
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-09
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-11-29 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.533(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.9095(5)
_cell_length_b                   5.86690(10)
_cell_length_c                   25.8562(6)
_cell_measurement_reflns_used    4696
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.0900
_cell_measurement_theta_min      3.6560
_cell_volume                     3514.94(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_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     17.00  51.00   0.50    0.05    --   90.32 -45.00  90.00   68
  2  \w     15.00  40.00   0.50    0.05    --   90.32 -45.00  30.00   50
  3  \w     22.00  49.00   0.50    0.05    --   90.32 -45.00  60.00   54
  4  \w     15.00  50.00   0.50    0.05    --   90.32 -45.00 120.00   70
  5  \w     75.00 165.00   0.50    0.05    --   90.32  53.00  22.00  180
  6  \w     37.00  67.00   0.50    0.05    --   90.32 -61.00 -90.00   60
  7  \w     18.00  49.00   0.50    0.05    --   90.32 -53.00-121.00   62
  8  \w     74.00 105.00   0.50    0.05    --   90.32 -94.00-180.00   62
  9  \w     35.00  61.00   0.50    0.05    --   90.32 -94.00-180.00   52
 10  \w   -118.00 -21.00   0.50    0.05    --  -43.34 -53.00-121.00  194
 11  \w   -117.00 -91.00   0.50    0.05    --  -43.34-125.00  30.00   52
 12  \w    -57.00  30.00   0.50    0.05    --  -43.34  53.00  22.00  174
 13  \w    -34.00  -8.00   0.50    0.05    --  -88.13  30.00  30.00   52
 14  \w    -60.00 -35.00   0.50    0.05    --  -88.13  53.00  22.00   50
 15  \w    -42.00 -11.00   0.50    0.05    --  -88.13  45.00   0.00   62
 16  \w    -51.00 -11.00   0.50    0.05    --  -88.13  45.00 -30.00   80
 17  \w    -69.00 -44.00   0.50    0.05    --  -88.13  61.00-150.00   50
 18  \w    -40.00 -15.00   0.50    0.05    --  -88.13  61.00-150.00   50
 19  \w    -46.00 -15.00   0.50    0.05    --  -88.13  45.00-180.00   62
 20  \w    -35.00 -10.00   0.50    0.05    --  -88.13  30.00-150.00   50
 21  \w    -34.00  -8.00   0.50    0.05    --  -88.13  30.00 -30.00   52
 22  \w    -35.00 -10.00   0.50    0.05    --  -88.13  30.00   0.00   50
 23  \w    -34.00  -8.00   0.50    0.05    --  -88.13  30.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0107355000
_diffrn_orient_matrix_UB_12      -0.1108040000
_diffrn_orient_matrix_UB_13      -0.0493545000
_diffrn_orient_matrix_UB_21      -0.0523904000
_diffrn_orient_matrix_UB_22      0.1283590000
_diffrn_orient_matrix_UB_23      -0.0408056000
_diffrn_orient_matrix_UB_31      0.0394826000
_diffrn_orient_matrix_UB_32      0.2005336000
_diffrn_orient_matrix_UB_33      -0.0011720000
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9079
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        65.823
_diffrn_reflns_theta_max         65.823
_diffrn_reflns_theta_min         3.675
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.043
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2 and n-hexane'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0446P)^2^+2.5117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2696
_reflns_number_total             2959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc01329d2.cif
_cod_data_source_block           cr-0724-1_auto
_cod_depositor_comments
'Adding full bibliography for 7246831--7246835.cif.'
_cod_database_code               7246832
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
1.b Idealised Me refined as rotating group:
 C1(H1C,H1A,H1B)
;
_shelx_res_checksum              35282
_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 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.850