Isolation of stable non cyclic 1,2-disulfoxides. Revisiting the thermolysis of S-aryl sulfinimines
Jose A. Souto; Willian Lewis; Robert A. Stockman; Chem.Commun. 50 (2014) 12630–; doi:10.1039/C4cc05751A

data_7115791
_publ_section_title
;
 Isolation of stable non cyclic 1,2-disulfoxides. Revisiting the
 thermolysis of S-aryl sulfinimines
;
_journal_name_full               Chem.Commun.
_journal_page_first              12630
_journal_paper_doi               10.1039/C4cc05751A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C14 H14 O2 S2'
_chemical_formula_sum            'C14 H14 O2 S2'
_chemical_formula_weight         278.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.432(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7235(12)
_cell_length_b                   7.5497(11)
_cell_length_c                   15.671(2)
_cell_measurement_reflns_used    1043
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.1250
_cell_measurement_theta_min      5.7100
_cell_volume                     671.47(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9458
_diffrn_measurement_details
;
  1 omega -127.00   29.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.6002    0.0000    0.0000 78

  2 omega -130.00 -102.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000 -125.0000 -180.0000 14

  3 omega -112.00  -84.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000 -125.0000   60.0000 14

  4 omega   93.00  157.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000  -60.0000 32

  5 omega   39.00   67.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000    0.0000 14

  6 omega   35.00   69.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  150.0000 17

  7 omega   34.00   62.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  120.0000 14

  8 omega   40.00   70.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   60.0000 15

  9 omega   34.00   66.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -180.0000 16

 10 omega   41.00   73.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000   60.0000 16

 11 omega  122.00  154.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   61.0000   60.0000 16

 12 omega   49.00   77.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000    0.0000 14

 13 omega   86.00  112.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000 -180.0000 13

 14 omega  131.00  157.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000 -180.0000 13

 15 omega   47.00   75.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000 -150.0000 14

 16 omega   41.00   73.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -30.0000 16

 17 omega   33.00   61.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   30.0000 14
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0674387000
_diffrn_orient_matrix_UB_12      0.0121081000
_diffrn_orient_matrix_UB_13      -0.0981979000
_diffrn_orient_matrix_UB_21      -0.2011789000
_diffrn_orient_matrix_UB_22      -0.1334271000
_diffrn_orient_matrix_UB_23      0.0052284000
_diffrn_orient_matrix_UB_31      -0.1695375000
_diffrn_orient_matrix_UB_32      0.1538879000
_diffrn_orient_matrix_UB_33      0.0122776000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2646
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.811
_diffrn_reflns_theta_min         6.519
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    3.519
_exptl_absorpt_correction_T_max  1.228
_exptl_absorpt_correction_T_min  0.518
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.612
_exptl_crystal_size_mid          0.2273
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0517
_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^+0.3241P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1086
_reflns_number_total             1306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc05751a2.cif
_cod_data_source_block           jasrsa
_cod_original_cell_volume        671.45(19)
_cod_database_code               7115791
_nottingham_internal_coll_name   JASRSA
_nottingham_internal_coll_number 12272
_nottingham_internal_coll_client JAS/RS
_nottingham_internal_coll_type   CUSTOM
_nottingham_internal_coll_frame_time 2
_nottingham_internal_coll_frame_width 2
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   4/3/2013
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 10/5/2013
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 10/5/2013
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 10/5/2013
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 10/5/2013
_nottingham_internal_archive_date 10/6/2013
_chemical_oxdiff_formula         'C14 H14 S2 O2'
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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,H,H,H) groups
2. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
 Sof(H9BD)=Sof(H9BE)=Sof(H9BF)=1-FVAR(2)
 Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
3.b Idealised Me refined as rotating group:
 C9(H9AA,H9AB,H9AC), C9(H9BD,H9BE,H9BF)
;
_shelxl_version_number           2013-2