Synthesis of α,α-Disulfenylated Aldehydes via Oxidative Transformation of Tertiary Amines.
Huang, Xin; Wang, Jichao; Ni, Zhangqin; Wang, Sichang; Pan, Yuanjiang; Organic letters 17 (2015) 5488–5491; doi:10.1021/acs.orglett.5b02876

data_1555428
_publ_section_title
;
 Synthesis of \a,\a-Disulfenylated Aldehydes via Oxidative Transformation
 of Tertiary Amines.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5488
_journal_page_last               5491
_journal_paper_doi               10.1021/acs.orglett.5b02876
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C15 H12 Cl2 O S2'
_chemical_formula_sum            'C15 H12 Cl2 O S2'
_chemical_formula_weight         343.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9371(4)
_cell_length_b                   9.8082(6)
_cell_length_c                   22.3442(12)
_cell_measurement_reflns_used    3619
_cell_measurement_temperature    171.5
_cell_measurement_theta_max      29.5979
_cell_measurement_theta_min      3.0686
_cell_volume                     1520.31(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      171.5
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0258305000
_diffrn_orient_matrix_UB_12      0.0548822000
_diffrn_orient_matrix_UB_13      0.0190493000
_diffrn_orient_matrix_UB_21      0.0329287000
_diffrn_orient_matrix_UB_22      -0.0469930000
_diffrn_orient_matrix_UB_23      0.0218414000
_diffrn_orient_matrix_UB_31      0.0932987000
_diffrn_orient_matrix_UB_32      0.0013983000
_diffrn_orient_matrix_UB_33      -0.0130018000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9254
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.5575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                1311
_reflns_number_total             1484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02876_si_001.cif
_cod_data_source_block           141201_hx_10_20_1
_cod_database_code               1555428
_chemical_oxdiff_formula         'c10 h10 o10 s21'
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Fixed Sof: O1(0.5) C6(0.5) H6(0.5) C6A(0.5) H6AA(0.5) H6AB(0.5) H6AC(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C9(H9)
3.b Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC)
;