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_7246834
_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 H17 Cl N S'
_chemical_formula_weight         362.88
_chemical_name_systematic
(Z)-7-chloro-3-methyl-N,4-diphenyl-1H-isothiochromen-1-imine
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 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                 92.516(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1263(3)
_cell_length_b                   6.9258(2)
_cell_length_c                   12.6138(4)
_cell_measurement_reflns_used    3003
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.2920
_cell_measurement_theta_min      4.3470
_cell_volume                     883.79(5)
_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 2018/2 (Sheldrick, 2018)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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    110.00 137.00   0.50    0.05    --   90.32  95.00  89.00   54
  2  \w     71.00  96.00   0.50    0.05    --   90.32  61.00 -30.00   50
  3  \w    122.00 165.00   0.50    0.05    --   90.32  61.00 -30.00   86
  4  \w     49.00 117.00   0.50    0.05    --   90.32-125.00 -60.00  136
  5  \w     52.00 116.00   0.50    0.05    --   90.32-125.00-150.00  128
  6  \w    -11.00  48.00   0.50    0.05    --   45.53 -95.00 -20.00  118
  7  \w     56.00  83.00   0.50    0.05    --   90.32-125.00 150.00   54
  8  \w     89.00 116.00   0.50    0.05    --   90.32-125.00 150.00   54
  9  \w     41.00  93.00   0.50    0.05    --   90.32 -95.00 -20.00  104
 10  \w     43.00 104.00   0.50    0.05    --   90.32 -77.00 -30.00  122
 11  \w     39.00  71.00   0.50    0.05    --   90.32 -61.00-120.00   64
 12  \w     19.00  46.00   0.50    0.05    --   90.32 -45.00-150.00   54
 13  \w     28.00  60.00   0.50    0.05    --   90.32 -77.00-150.00   64
 14  \w     71.00 105.00   0.50    0.05    --   90.32 -77.00-150.00   68
 15  \w    -29.00  41.00   0.50    0.05    --   45.53 -37.00  60.00  140
 16  \w     19.00  50.00   0.50    0.05    --   90.32 -45.00 120.00   62
 17  \w   -116.00 -89.00   0.50    0.05    --  -43.34-125.00 -30.00   54
 18  \w   -139.00 -97.00   0.50    0.05    --  -88.13 -95.00 -20.00   84
 19  \w   -116.00 -59.00   0.50    0.05    --  -43.34 -77.00  30.00  114
 20  \w    -56.00 -19.00   0.50    0.05    --  -43.34 -77.00  30.00   74
 21  \w    -25.00  20.00   0.50    0.05    --  -43.34  19.00 -90.00   90
 22  \w    -43.00 -16.00   0.50    0.05    --  -88.13  61.00 -60.00   54
 23  \w    -48.00 -12.00   0.50    0.05    --  -88.13  45.00   0.00   72
 24  \w    -43.00 -14.00   0.50    0.05    --  -88.13  45.00  30.00   58
 25  \w    -48.00 -13.00   0.50    0.05    --  -88.13  45.00  60.00   70
 26  \w    -50.00 -11.00   0.50    0.05    --  -88.13  45.00  90.00   78
 27  \w    -41.00 -11.00   0.50    0.05    --  -88.13  45.00 120.00   60
 28  \w    -35.00 -10.00   0.50    0.05    --  -88.13  30.00 120.00   50
 29  \w    -34.00  -8.00   0.50    0.05    --  -88.13  30.00  90.00   52
 30  \w    -35.00 -10.00   0.50    0.05    --  -88.13  30.00 -60.00   50
 31  \w    -51.00 -11.00   0.50    0.05    --  -88.13  45.00 -60.00   80
 32  \w    -47.00 -11.00   0.50    0.05    --  -88.13  45.00-120.00   72
 33  \w    -35.00  -9.00   0.50    0.05    --  -88.13  30.00-150.00   52
 34  \w    -35.00  -8.00   0.50    0.05    --  -88.13  30.00-120.00   54
 35  \w    -35.00 -10.00   0.50    0.05    --  -88.13  30.00 -90.00   50
 36  \w    -35.00 -10.00   0.50    0.05    --  -88.13  30.00  60.00   50
 37  \w    -82.00 -54.00   0.50    0.05    --  -88.13  95.00  89.00   56
 38  \w    -88.00 -55.00   0.50    0.05    --  -88.13 125.00  90.00   66
 39  \w    -49.00 -13.00   0.50    0.05    --  -88.13 125.00  90.00   72
 40  \w    -65.00  21.00   0.50    0.05    --  -43.34  95.00  89.00  172
;
_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      0.0495143000
_diffrn_orient_matrix_UB_12      0.1265931000
_diffrn_orient_matrix_UB_13      0.0939919000
_diffrn_orient_matrix_UB_21      0.0365336000
_diffrn_orient_matrix_UB_22      -0.1830060000
_diffrn_orient_matrix_UB_23      0.0643551000
_diffrn_orient_matrix_UB_31      0.1392157000
_diffrn_orient_matrix_UB_32      0.0031130000
_diffrn_orient_matrix_UB_33      -0.0443814000
_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  0.0727
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8365
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        65.651
_diffrn_reflns_theta_max         65.651
_diffrn_reflns_theta_min         3.507
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.026
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             378
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2 and n-hexane'
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0342
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1488
_reflns_number_total             1643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc01329d2.cif
_cod_data_source_block           cr-0724-2
_cod_depositor_comments
'Adding full bibliography for 7246831--7246835.cif.'
_cod_database_code               7246834
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1. Others
 Fixed Sof: H18A(0.5) H18B(0.5) H18C(0.5)
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              38087
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.478
_oxdiff_exptl_absorpt_empirical_full_min 0.883