One-Pot Synthesis of β-Hydroxysulfones and Its Application in the Preparation of Anticancer Drug Bicalutamide.
Wang, Yajun; Jiang, Wei; Huo, Congde; The Journal of organic chemistry 82 (2017) 10628–10634; doi:10.1021/acs.joc.7b01371

data_4032849
_publ_section_title
;
 One-Pot Synthesis of \b-Hydroxysulfones and Its Application in the
 Preparation of Anticancer Drug Bicalutamide.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10628
_journal_page_last               10634
_journal_paper_doi               10.1021/acs.joc.7b01371
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H16 O3 S'
_chemical_formula_sum            'C15 H16 O3 S'
_chemical_formula_weight         276.34
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.79(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3223(13)
_cell_length_b                   5.9112(9)
_cell_length_c                   16.224(5)
_cell_measurement_reflns_used    124
_cell_measurement_temperature    291.13(10)
_cell_measurement_theta_max      15.2600
_cell_measurement_theta_min      3.8850
_cell_volume                     700.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.13(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -11.00   19.00   2.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   90.0000 15

  2 omega   -1.00   91.00   2.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -30.0000 46

  3 omega  -53.00   59.00   2.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  -30.0000 56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0365732000
_diffrn_orient_matrix_UB_12      -0.0195705000
_diffrn_orient_matrix_UB_13      0.0409178000
_diffrn_orient_matrix_UB_21      -0.0894416000
_diffrn_orient_matrix_UB_22      -0.0220879000
_diffrn_orient_matrix_UB_23      0.0124840000
_diffrn_orient_matrix_UB_31      0.0109504000
_diffrn_orient_matrix_UB_32      -0.1163179000
_diffrn_orient_matrix_UB_33      -0.0090913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.3113
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2632
_diffrn_reflns_point_group_measured_fraction_full 0.836
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_min         3.631
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2270
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.3150
_refine_ls_R_factor_gt           0.1057
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.2160
_reflns_Friedel_coverage         0.496
_reflns_Friedel_fraction_full    0.640
_reflns_Friedel_fraction_max     0.607
_reflns_number_gt                609
_reflns_number_total             2270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01371_si_003.cif
_cod_data_source_block           wangyj_0425
_cod_depositor_comments
'Adding full bibliography for 4032849--4032850.cif.'
_cod_database_code               4032849
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Restrained distances
 H1-O1
 1 with sigma of 0.05
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(O1) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.006 and sigma
for terminal atoms of 0.008
4.a Ternary CH refined with riding coordinates:
 C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              85637
_shelx_hkl_checksum              11690
_olex2_date_sample_data_collection 2017-04-26
_olex2_submission_special_instructions 'No special instructions were received'