Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights.
Wu, Qiuyue; Dong, Ziyang; Xu, Jiaxi; Yang, Zhanhui; Organic & biomolecular chemistry 19 (2021) 3173–3180; doi:10.1039/d1ob00116g

data_7157949
_publ_section_title
;
 Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of
 thioacyl carbenes with alk-2-enals and mechanistic insights.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3173
_journal_page_last               3180
_journal_paper_doi               10.1039/d1ob00116g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C16 H18 O3 S'
_chemical_formula_sum            'C16 H18 O3 S'
_chemical_formula_weight         290.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-11-06
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2019-05-30 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 136.68(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.860(3)
_cell_length_b                   8.4885(4)
_cell_length_c                   14.325(2)
_cell_measurement_reflns_used    1990
_cell_measurement_temperature    105.6
_cell_measurement_theta_max      70.9331
_cell_measurement_theta_min      4.4953
_cell_volume                     1490.0(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      105.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details
;
  1 omega  -49.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -180.0000 30

  2 omega  -46.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  159.0000  -70.0000 25

  3 omega  -12.00   13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -180.0000 25

  4 omega   10.00   37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -120.0000 27

  5 omega   72.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -120.0000 32

  6 omega   28.00   54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   90.0000 26

  7 omega   10.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  150.0000 92

  8 omega  -28.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   90.0000 28

  9 omega  -25.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000   30.0000 59

 10 omega   41.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 48

 11 omega   82.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 94

 12 omega   92.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 84

 13 omega  128.00  165.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  159.0000  102.0000 37

 14 omega   44.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 48

 15 omega   65.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -118.0000 -136.0000 49

 16 omega   43.00  135.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 92

 17 omega   73.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -30.0000 32
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0647716000
_diffrn_orient_matrix_UB_12      0.0117602000
_diffrn_orient_matrix_UB_13      -0.1507210000
_diffrn_orient_matrix_UB_21      -0.0108636000
_diffrn_orient_matrix_UB_22      0.1793633000
_diffrn_orient_matrix_UB_23      0.0036243000
_diffrn_orient_matrix_UB_31      0.1072302000
_diffrn_orient_matrix_UB_32      0.0248605000
_diffrn_orient_matrix_UB_33      0.0431681000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2624
_diffrn_reflns_point_group_measured_fraction_full 0.566
_diffrn_reflns_point_group_measured_fraction_max 0.550
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.071
_diffrn_reflns_theta_min         6.069
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.031(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1579
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0566P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0755
_reflns_Friedel_coverage         0.148
_reflns_Friedel_fraction_full    0.152
_reflns_Friedel_fraction_max     0.142
_reflns_number_gt                1569
_reflns_number_total             1579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00116g2.cif
_cod_data_source_block           exp_5184
_cod_depositor_comments          'Adding full bibliography for 7157949.cif.'
_cod_original_cell_volume        1489.9(7)
_cod_database_code               7157949
_reflns_odcompleteness_completeness 97.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.784
_shelx_estimated_absorpt_t_min   0.757
_shelx_res_checksum              17765
_shelx_shelxl_version_number     2014/7