Auto-oxidative hydroxysulfenylation of alkenes
Congde Huo; Yajun Wang; Yong Yuan; Fengjuan Chen; Jing Tang; Chem.Commun. 52 (2016) 7233–; doi:

data_7118970
_publ_section_title
;
 Auto-oxidative hydroxysulfenylation of alkenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              7233
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H39 O4 S'
_chemical_formula_sum            'C30 H40 O4 S'
_chemical_formula_weight         496.68
_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
_audit_creation_date             2015-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-01-06 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.617(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.5064(8)
_cell_length_b                   5.8689(4)
_cell_length_c                   17.8643(15)
_cell_measurement_reflns_used    661
_cell_measurement_temperature    273.77(10)
_cell_measurement_theta_max      48.9000
_cell_measurement_theta_min      4.6230
_cell_volume                     1381.87(17)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      273.77(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega  -29.00   20.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000    0.0000 33

  2 omega  -14.00   61.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   90.0000 50

  3 omega   36.00  115.50   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 53

  4 omega   42.00  115.50   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 49

  5 omega   70.00  127.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000  -30.0000 38

  6 omega   87.00  168.00   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 54

  7 omega  105.00  141.00   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 24

  8 omega   57.00  150.00   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 62

  9 omega  117.00  168.00   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  120.0000 34

 10 omega   39.00   93.00   1.5000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 36

 11 omega   25.00   91.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -90.0000 44

 12 omega   11.00   65.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000  -30.0000 36

 13 omega    5.00   33.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 19

 14 omega   35.00   62.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 18
;
_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      0.0071499000
_diffrn_orient_matrix_UB_12      0.2426764000
_diffrn_orient_matrix_UB_13      0.0335949000
_diffrn_orient_matrix_UB_21      0.0361494000
_diffrn_orient_matrix_UB_22      -0.0985249000
_diffrn_orient_matrix_UB_23      0.0813282000
_diffrn_orient_matrix_UB_31      0.1109629000
_diffrn_orient_matrix_UB_32      0.0164318000
_diffrn_orient_matrix_UB_33      -0.0082489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4853
_diffrn_reflns_point_group_measured_fraction_full 0.712
_diffrn_reflns_point_group_measured_fraction_max 0.698
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.703
_diffrn_reflns_theta_min         3.736
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.289
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0685P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1783
_reflns_Friedel_coverage         0.286
_reflns_Friedel_fraction_full    0.360
_reflns_Friedel_fraction_max     0.347
_reflns_number_gt                2067
_reflns_number_total             3623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc01937d2.cif
_cod_data_source_block           wangyj_1228_2
_cod_original_cell_volume        1381.88(17)
_cod_database_code               7118970
_reflns_odcompleteness_completeness 99.71
_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. Restrained distances
 H4-O4
 0.86 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C30) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C17(H17)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C15(H15A,H15B), C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C24(H24), C25(H25), C27(H27), C28(H28)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-28
_olex2_submission_special_instructions 'No special instructions were received'