Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Sulfones: A Tool To Access Highly Substituted Vinyl Sulfones.
Waiba, Satyadeep; Barman, Milan K.; Maji, Biplab; The Journal of organic chemistry 84 (2019) 973–982; doi:10.1021/acs.joc.8b02911

data_4036023
_publ_section_title
;
 Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols
 With Sulfones: A Tool To Access Highly Substituted Vinyl Sulfones.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              973
_journal_page_last               982
_journal_paper_doi               10.1021/acs.joc.8b02911
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C21 H17 Cl O3 S'
_chemical_formula_sum            'C21 H17 Cl O3 S'
_chemical_formula_weight         384.86
_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             2018-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.302(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.65790(10)
_cell_length_b                   21.7190(5)
_cell_length_c                   14.8462(3)
_cell_measurement_reflns_used    9761
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.3390
_cell_measurement_theta_min      1.8360
_cell_volume                     1824.33(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.933
_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    -16.00 111.00   1.00   21.00    --   26.72  77.00-150.00  127
  2  \w    -16.00 111.00   1.00   21.00    --   26.72  77.00  90.00  127
  3  \w    -16.00 111.00   1.00   21.00    --   26.72  77.00 -30.00  127
  4  \w   -119.00 -55.00   1.00   21.00    --  -23.50 178.00-180.00   64
  5  \w    -61.00  52.00   1.00   21.00    --  -23.50  57.00-120.00  113
  6  \w    -49.00  65.00   1.00   21.00    --   26.72 -57.00 -30.00  114
  7  \w    -11.00  18.00   1.00   21.00    --   26.72  57.00 -60.00   29
  8  \w     35.00 121.00   1.00   21.00    --   26.72 178.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0130294000
_diffrn_orient_matrix_UB_12      -0.0267079000
_diffrn_orient_matrix_UB_13      -0.0270468000
_diffrn_orient_matrix_UB_21      0.1210192000
_diffrn_orient_matrix_UB_22      0.0018271000
_diffrn_orient_matrix_UB_23      -0.0121027000
_diffrn_orient_matrix_UB_31      0.0304769000
_diffrn_orient_matrix_UB_32      -0.0186652000
_diffrn_orient_matrix_UB_33      0.0374691000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20331
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.656
_diffrn_reflns_theta_min         1.661
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0290P)^2^+1.4791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3423
_reflns_number_total             3988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02911_si_002.cif
_cod_data_source_block           mba-144
_cod_database_code               4036023
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O Cl S'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.913
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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:
 C4(H4), C15(H15), C5(H5), C2(H2), C8(H8), C6(H6), C11(H11), C13(H13),
 C17(H17), C21(H21), C12(H12), C19(H19), C20(H20), C18(H18)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              72351
_shelx_hkl_checksum              70080
_olex2_date_sample_data_collection 2018-07-18
_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 1.327
_oxdiff_exptl_absorpt_empirical_full_min 0.739