Synthesis of β-Hydroxysulfones from Sulfonyl Chlorides and Alkenes Utilizing Visible Light Photocatalytic Sequences.
Pagire, Santosh K.; Paria, Suva; Reiser, Oliver; Organic letters 18 (2016) 2106–2109; doi:10.1021/acs.orglett.6b00734

data_1555536
_publ_section_title
;
 Synthesis of \b-Hydroxysulfones from Sulfonyl Chlorides and Alkenes
 Utilizing Visible Light Photocatalytic Sequences.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2106
_journal_page_last               2109
_journal_paper_doi               10.1021/acs.orglett.6b00734
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 Br O3 S'
_chemical_formula_sum            'C15 H15 Br O3 S'
_chemical_formula_weight         355.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-28
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.755(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.92604(15)
_cell_length_b                   12.2676(3)
_cell_length_c                   9.9444(2)
_cell_measurement_reflns_used    4600
_cell_measurement_temperature    123.0(2)
_cell_measurement_theta_max      72.5910
_cell_measurement_theta_min      3.6220
_cell_volume                     702.21(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.37b (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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1818
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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   -123.00 -90.00   1.00    1.00    --  -42.89 -99.00 -30.00   33
  2  \w    -61.00  27.00   1.00    1.00    --  -42.89  57.00 -90.00   88
  3  \w   -112.00 -80.00   1.00    1.00    --  -42.89 -99.00   0.00   32
  4  \w     79.00 166.00   1.00    1.00    --  104.50  30.00   0.00   87
  5  \w     31.00  91.00   1.00    1.00    --  104.50 -30.00  30.00   60
  6  \w     32.00  81.00   1.00    1.00    --  104.50 -30.00  90.00   49
  7  \w     42.00  90.00   1.00    1.00    --  104.50 -30.00-150.00   48
  8  \w     47.00  82.00   1.00    1.00    --  104.50 -30.00 -30.00   35
  9  \w     49.00 114.00   1.00    1.00    --  104.50 -61.00 -90.00   65
 10  \w     11.00 117.00   1.00    1.00    --   42.89  77.00 150.00  106
 11  \w     17.00 113.00   1.00    1.00    --   42.89  57.00 -60.00   96
 12  \w     31.00 121.00   1.00    1.00    --  104.50-125.00 -90.00   90
 13  \w     78.00 178.00   1.00    1.00    --  104.50  30.00  60.00  100
 14  \w     73.00 178.00   1.00    1.00    --  104.50  77.00 -90.00  105
 15  \w     65.00 178.00   1.00    1.00    --  104.50  15.00-180.00  113
 16  \w     34.00 130.00   1.00    1.00    --   42.89-178.00-180.00   96
 17  \w     11.00 117.00   1.00    1.00    --   42.89  77.00  30.00  106
 18  \w     73.00 128.00   1.00    1.00    --  104.50  77.00-150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0022009000
_diffrn_orient_matrix_UB_12      -0.0392986000
_diffrn_orient_matrix_UB_13      0.1473981000
_diffrn_orient_matrix_UB_21      -0.2159427000
_diffrn_orient_matrix_UB_22      0.0701932000
_diffrn_orient_matrix_UB_23      -0.0009077000
_diffrn_orient_matrix_UB_31      -0.1580660000
_diffrn_orient_matrix_UB_32      -0.0964158000
_diffrn_orient_matrix_UB_33      -0.0610168000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5956
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.353
_diffrn_reflns_theta_min         4.578
_diffrn_source                   'gradient vaccum rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.423
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.37b (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.102
_refine_diff_density_max         1.071
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 1138 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0720P)^2^+1.0276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.870
_reflns_number_gt                2616
_reflns_number_total             2628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00734_si_002.cif
_cod_data_source_block           o086
_cod_database_code               1555536
_chemical_oxdiff_formula         'C16 H19 S O2 Br'
_chemical_oxdiff_usercomment     'Reiser, Pagire'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C15(H15), C11(H11), C13(H13), C14(H14), C4(H4), C5(H5),
 C12(H12)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_shelx_res_checksum              6698
_shelx_hkl_checksum              77000
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-20
_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 2.730
_oxdiff_exptl_absorpt_empirical_full_min 0.620