Reactions of thioalkynes with diarylketenes <i>via</i> [3+2]-annulation <i>versus</i> benzannulation using Au and P(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> catalysts.
More, Sayaji Arjun; Sadaphal, Vikas Ashokrao; Kuo, Tung-Chun; Cheng, Mu-Jeng; Liu, Rai-Shung; Chemical communications (Cambridge, England) 58 (2022) 10064–10067; doi:10.1039/d2cc03613d

data_7130814
_publ_section_title
;
 Reactions of thioalkynes with diarylketenes <i>via</i> [3+2]-annulation
 <i>versus</i> benzannulation using Au and
 P(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> catalysts.
;
_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10064
_journal_page_last               10067
_journal_paper_doi               10.1039/d2cc03613d
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C24 H20 O2 S'
_chemical_formula_sum            'C24 H20 O2 S'
_chemical_formula_weight         372.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-08
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2021-12-08 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.154(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9643(3)
_cell_length_b                   10.0272(2)
_cell_length_c                   13.3690(3)
_cell_measurement_reflns_used    7764
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.3350
_cell_measurement_theta_min      5.4050
_cell_volume                     1861.18(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_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-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     73.00  98.00   0.50    1.56    --   78.57-119.00 -35.50   50
  2  \w     27.00  52.00   0.50    1.56    --   57.89-128.00-142.00   50
  3  \w     44.00  94.00   0.50    1.56    --   71.10-128.00-142.00  100
  4  \w     37.00  97.00   0.50    1.56    --   78.57-118.00-114.46  120
  5  \w     41.00  66.00   0.50    1.56    --   74.39-128.00-142.00   50
  6  \w     61.00  98.00   0.50    1.56    --   78.57-121.00-144.14   74
  7  \w     37.00  77.00   0.50    1.56    --   57.89  15.00-180.00   80
  8  \w     53.00 119.00   0.50    1.56    --   74.39  15.00  90.00  132
  9  \w   -100.00 -45.00   0.50    1.56    --  -60.74 -15.00   0.00  110
 10  \w   -108.00 -61.00   0.50    1.56    --  -73.75 -15.00  30.00   94
 11  \w   -105.00 -62.00   0.50    1.56    --  -60.74 -15.00  90.00   86
 12  \w   -117.00 -58.00   0.50    1.56    --  -73.75 -15.00 150.00  118
 13  \w    -91.00 -44.00   0.50    1.56    --  -60.74 -15.00 -60.00   94
 14  \w   -118.00 -57.00   0.50    1.56    --  -73.68 -15.00 -90.00  122
 15  \w    -94.00 -57.00   0.50    1.56    --  -73.75 -15.00-150.00   74
 16  \w    -83.00 -57.00   0.50    1.56    --  -60.74 -15.00-180.00   52
 17  \w    -69.00 -39.00   0.50    1.56    --  -78.57 116.00 -87.59   60
 18  \w    -73.00 -26.00   0.50    1.56    --  -60.74 125.00   0.00   94
 19  \w    -70.00 -45.00   0.50    1.56    --  -60.74 128.00 -67.00   50
 20  \w    -74.00 -48.00   0.50    1.56    --  -73.68 128.00 -67.00   52
 21  \w    -96.00 -45.00   0.50    1.56    --  -73.75 125.00-120.00  102
 22  \w    -98.00 -38.00   0.50    1.56    --  -78.57 120.00-150.48  120
 23  \w    -96.00 -54.00   0.50    1.56    --  -73.75 125.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0289699000
_diffrn_orient_matrix_UB_12      0.0075265000
_diffrn_orient_matrix_UB_13      0.1078318000
_diffrn_orient_matrix_UB_21      -0.1069974000
_diffrn_orient_matrix_UB_22      0.0054269000
_diffrn_orient_matrix_UB_23      -0.0422920000
_diffrn_orient_matrix_UB_31      -0.0052045000
_diffrn_orient_matrix_UB_32      -0.1533619000
_diffrn_orient_matrix_UB_33      0.0037613000
_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  0.0214
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14032
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         3.183
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.33a (Rigaku Oxford Diffraction, 2021)
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    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0426P)^2^+0.6441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2940
_reflns_number_total             3307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03613d2.cif
_cod_data_source_block           211216lt_auto
_cod_database_code               7130814
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C96  H80  O8  S4  '
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.814
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              24633
_shelx_hkl_checksum              35474
_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 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.618