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_7115793
_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_absolute_configuration ad
_chemical_formula_moiety         'C14 H14 S2'
_chemical_formula_sum            'C14 H14 S2'
_chemical_formula_weight         246.37
_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   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                 94.682(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5701(7)
_cell_length_b                   5.7018(6)
_cell_length_c                   14.6979(13)
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.1400
_cell_measurement_theta_min      3.0040
_cell_volume                     632.29(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_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 10.6296
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.8958
_diffrn_measurement_details
;
  1 omega  -99.00  -59.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000 -156.0000   67.0000 20

  2 omega  -45.00   33.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -60.0000 39

  3 omega   54.00  108.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573  156.0000  104.0000 27

  4 omega   73.00  103.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573   57.0000  120.0000 15

  5 omega   15.00   99.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573   57.0000   30.0000 42

  6 omega   43.00   85.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573   38.0000  -30.0000 21

  7 omega   77.00  103.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   61.0000  -30.0000 13

  8 omega  114.00  170.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   77.0000  -90.0000 28

  9 omega   34.00   68.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -45.0000   30.0000 17

 10 omega   74.00  100.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   77.0000  -90.0000 13

 11 omega   80.00  106.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   61.0000  -60.0000 13

 12 omega   78.00  106.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   61.0000    0.0000 14

 13 omega  147.00  173.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   30.0000 -150.0000 13

 14 omega   40.00   88.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -77.0000   30.0000 24

 15 omega   72.00  118.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526 -119.0000 -136.0000 23

 16 omega   83.00  135.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   30.0000 -150.0000 26

 17 omega  117.00  169.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   77.0000  -60.0000 26

 18 omega   74.00  100.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   77.0000  -60.0000 13

 19 omega   79.00  119.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   61.0000   30.0000 20

 20 omega   74.00  102.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   77.0000  -30.0000 14

 21 omega   60.00   90.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -30.0000  -60.0000 15

 22 omega   73.00   99.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   77.0000    0.0000 13

 23 omega   90.00  174.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   35.0000 -120.0000 42

 24 omega   33.00   89.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -94.0000  120.0000 28

 25 omega   74.00  100.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   77.0000   30.0000 13

 26 omega   86.00  138.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   45.0000    0.0000 26

 27 omega   53.00   79.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -94.0000  -30.0000 13
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1826711000
_diffrn_orient_matrix_UB_12      0.1146376000
_diffrn_orient_matrix_UB_13      0.0071674000
_diffrn_orient_matrix_UB_21      0.0182204000
_diffrn_orient_matrix_UB_22      -0.0378757000
_diffrn_orient_matrix_UB_23      0.1041308000
_diffrn_orient_matrix_UB_31      0.0893050000
_diffrn_orient_matrix_UB_32      0.2417218000
_diffrn_orient_matrix_UB_33      0.0129840000
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4647
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.546
_diffrn_reflns_theta_min         3.017
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    3.545
_exptl_absorpt_correction_T_max  1.190
_exptl_absorpt_correction_T_min  0.346
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
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    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.5996
_exptl_crystal_size_mid          0.2451
_exptl_crystal_size_min          0.0366
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.132(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0380P)^2^+0.1738P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0819
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                2278
_reflns_number_total             2393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc05751a2.cif
_cod_data_source_block           jsrscb
_cod_original_cell_volume        632.29(10)
_cod_database_code               7115793
_nottingham_internal_coll_name   JSRSCB
_nottingham_internal_coll_number 12490
_nottingham_internal_coll_client JAS/RS
_nottingham_internal_coll_type   CUSTOM
_nottingham_internal_coll_frame_time '2 AND 4'
_nottingham_internal_coll_frame_width 2
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   24/5/2013
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 24/5/2013
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 24/5/2013
_nottingham_internal_refinement_user AW
_nottingham_internal_refinement_date 10/6/2013
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 10/6/2013
_nottingham_internal_archive_date 10/6/2013
_chemical_oxdiff_formula         'C14 H14 S2'
_chemical_oxdiff_usercomment
'JSRSCB #12490 IN FOMBLIN FILM ON MICROMOUNT FOR JS/RS'
_reflns_odcompleteness_completeness 99.84
_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) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
;
_shelxl_version_number           2013-2