Catalytic asymmetric sulfenylation to structurally diverse dithioketals
Kui Liao; Feng Zhou; Jin-Sheng Yu; Wei-Ming Gao; Jian Zhou; Chem.Commun. 51 (2015) 16255–; doi:10.1039/C5cc07010D

data_7118027
_publ_section_title
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 Catalytic asymmetric sulfenylation to structurally diverse dithioketals
;
_journal_name_full               Chem.Commun.
_journal_page_first              16255
_journal_paper_doi               10.1039/C5cc07010D
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H15 F3 O3 S2'
_chemical_formula_sum            'C18 H15 F3 O3 S2'
_chemical_formula_weight         400.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-20 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1691(14)
_cell_length_b                   38.663(4)
_cell_length_c                   7.1029(8)
_cell_measurement_reflns_used    7143
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.40
_cell_measurement_theta_min      2.211
_cell_volume                     3616.5(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            35999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.474
_diffrn_reflns_theta_min         1.634
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0715 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.8705.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         10915
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.252
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0672
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.2020
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6742
_reflns_number_total             10915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc07010d2.cif
_cod_data_source_block           dm15546
_cod_database_code               7118027
_shelxl_version_number           2014-3
_olex2_refinement_description
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1. Twinned data refinement
 Scales: 0.98(12) 0.02(12)
2. 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
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim C10: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
F4 \\sim F5 \\sim F6 \\sim C28: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C10) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C28) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F5) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C27(H27A,H27B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C22(H22),
 C25(H25), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C)
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_shelx_res_checksum              97493
_shelx_hkl_checksum              59202
_olex2_submission_special_instructions 'No special instructions were received'