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_7246833
_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 Br N S'
_chemical_formula_sum            'C22 H16 Br N S'
_chemical_formula_weight         406.33
_chemical_melting_point          112
_chemical_name_systematic
(Z)-7-bromo-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                 92.802(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2654(2)
_cell_length_b                   7.04540(10)
_cell_length_c                   12.4963(3)
_cell_measurement_reflns_used    3048
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.3480
_cell_measurement_theta_min      3.5270
_cell_volume                     902.70(3)
_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 0.963
_diffrn_measured_fraction_theta_max 0.963
_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     19.00  44.00   0.50    0.08    --   90.32 -45.00-150.00   50
  2  \w     16.00  41.00   0.50    0.08    --   90.32 -45.00-180.00   50
  3  \w     32.00  79.00   0.50    0.08    --   90.32 -66.00 -13.00   94
  4  \w     14.00  49.00   0.50    0.08    --   90.32 -45.00  60.00   70
  5  \w     17.00  47.00   0.50    0.08    --   90.32 -45.00 150.00   60
  6  \w     80.00 163.00   0.50    0.08    --   90.32  66.00 121.00  166
  7  \w    -67.00  30.00   0.50    0.05    --  -43.09  66.00 121.00  194
  8  \w    -78.00 -23.00   0.50    0.08    --  -88.13  66.00 121.00  110
  9  \w    -49.00 -12.00   0.50    0.08    --  -88.13  45.00  90.00   74
 10  \w    -38.00 -11.00   0.50    0.08    --  -88.13  45.00  60.00   54
 11  \w    -39.00 -14.00   0.50    0.08    --  -88.13  45.00  30.00   50
 12  \w    -35.00 -10.00   0.50    0.08    --  -88.13  30.00  60.00   50
 13  \w    -35.00  -8.00   0.50    0.08    --  -88.13  30.00 -90.00   54
 14  \w    -40.00 -13.00   0.50    0.08    --  -88.13  45.00-120.00   54
 15  \w    -37.00 -11.00   0.50    0.08    --  -88.13  45.00-150.00   52
 16  \w    -34.00  -8.00   0.50    0.08    --  -88.13  30.00-120.00   52
 17  \w    -35.00  -8.00   0.50    0.08    --  -88.13  30.00 -60.00   54
 18  \w    -35.00 -10.00   0.50    0.08    --  -88.13  30.00  90.00   50
 19  \w    -91.00 -15.00   0.50    0.08    --  -88.13 125.00 120.00  152
 20  \w   -106.00 -20.00   0.50    0.05    --  -43.09 -66.00 -13.00  172
 21  \w   -116.00 -82.00   0.50    0.05    --  -43.09-125.00 150.00   68
;
_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      0.0708102000
_diffrn_orient_matrix_UB_12      0.0975998000
_diffrn_orient_matrix_UB_13      -0.0909000000
_diffrn_orient_matrix_UB_21      0.0687674000
_diffrn_orient_matrix_UB_22      0.1344117000
_diffrn_orient_matrix_UB_23      0.0820807000
_diffrn_orient_matrix_UB_31      0.1132417000
_diffrn_orient_matrix_UB_32      -0.1423633000
_diffrn_orient_matrix_UB_33      0.0150623000
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4894
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        65.808
_diffrn_reflns_theta_max         65.808
_diffrn_reflns_theta_min         3.541
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.194
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.422
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2 and n-hexane'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0578P)^2^+0.0728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1531
_reflns_number_total             1648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc01329d2.cif
_cod_data_source_block           cr-br-up-0807_auto
_cod_depositor_comments
'Adding full bibliography for 7246831--7246835.cif.'
_cod_database_code               7246833
_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:
 C7(H7), C9(H9), C10(H10), C16(H16), C14(H14), C3(H3), C15(H15), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              9119
_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 1.415
_oxdiff_exptl_absorpt_empirical_full_min 0.803