Catalytic (3 + 2) umpolung annulations of α-thioacyl carbenes with aryl isothiocyanates
Dong, Ziyang; Ma, Meng-Yao; Xu, Jiaxi; Yang, Zhanhui; Chemical Communications  (2022) –; doi:10.1039/D2CC02882D

data_7130292
_publ_section_title
;
 Catalytic (3 + 2) umpolung annulations of \a-thioacyl carbenes with aryl
 isothiocyanates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02882D
_journal_year                    2022
_chemical_formula_moiety         'C18 H14 Br N O2 S2'
_chemical_formula_sum            'C18 H14 Br N O2 S2'
_chemical_formula_weight         420.33
_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     direct
_atom_sites_solution_secondary   difmap
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  Olex2 1.1
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_audit_update_record
;
2021-07-20 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.625(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3517(4)
_cell_length_b                   20.2201(10)
_cell_length_c                   11.9402(5)
_cell_measurement_reflns_used    1950
_cell_measurement_temperature    116.10(10)
_cell_measurement_theta_max      27.6830
_cell_measurement_theta_min      3.5550
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
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'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
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_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.8310
_diffrn_measurement_details
;
  1 omega   29.00   81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   77.0000 -120.0000 52

  2 omega   48.00   85.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  178.0000 -180.0000 37

  3 omega  -20.00   27.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000 -180.0000 47

  4 omega  -21.00   54.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  -99.0000    0.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0453875000
_diffrn_orient_matrix_UB_12      -0.0215932000
_diffrn_orient_matrix_UB_13      0.0382658000
_diffrn_orient_matrix_UB_21      -0.0015267000
_diffrn_orient_matrix_UB_22      0.0249007000
_diffrn_orient_matrix_UB_23      0.0418592000
_diffrn_orient_matrix_UB_31      -0.0851662000
_diffrn_orient_matrix_UB_32      -0.0119829000
_diffrn_orient_matrix_UB_33      0.0178048000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7333
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75954
_exptl_absorpt_correction_type   multi-scan
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0271P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                2689
_reflns_number_total             3407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc02882d2.cif
_cod_data_source_block           exp_7395
_cod_original_cell_volume        1774.23(14)
_cod_database_code               7130292
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07