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_7115792
_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         'C18 H22 O2 S2'
_chemical_formula_sum            'C18 H22 O2 S2'
_chemical_formula_weight         334.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                84.776(10)
_cell_angle_beta                 69.822(12)
_cell_angle_gamma                61.946(15)
_cell_formula_units_Z            1
_cell_length_a                   7.5624(11)
_cell_length_b                   8.0233(11)
_cell_length_c                   8.1209(9)
_cell_measurement_reflns_used    4466
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.9720
_cell_measurement_theta_min      5.7970
_cell_volume                     406.65(12)
_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    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_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 0.9976
_diffrn_measured_fraction_theta_max 0.9845
_diffrn_measurement_details
;
  1 omega  -49.00  -13.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -61.0000  -30.0000 18

  2 omega -107.00  -53.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -45.0000  150.0000 27

  3 omega  -50.00   10.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  150.0000 30

  4 omega  -66.00   32.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   77.0000 -180.0000 49

  5 omega  -33.00   -3.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  -60.0000 15

  6 omega  -42.00  -16.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -45.0000  150.0000 13

  7 omega  -91.00  -37.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  -60.0000 27

  8 omega  -62.00   30.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -60.0000 46

  9 omega   10.00   36.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   84.0000   54.1146 13

 10 omega    7.00   33.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   89.0000  -72.8750 13

 11 omega    6.00   32.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   90.0000  158.4585 13

 12 omega   19.00   45.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000 -150.2471 13

 13 omega   18.00   44.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000  -52.3054 13

 14 omega   20.00   46.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000   72.3629 13

 15 omega   30.00   56.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   71.0000   21.5915 13

 16 omega   29.00   55.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000 -115.5614 13

 17 omega   32.00   68.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000  148.4010 18

 18 omega   35.00   63.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   63.0000  -37.3554 14

 19 omega   34.00   64.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  -31.4658 15

 20 omega   34.00   84.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   72.0000   95.1257 25

 21 omega   37.00   85.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000   34.0855 24

 22 omega   45.00   99.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   72.0000 -130.0588 27

 23 omega   49.00   93.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   76.0000  174.0776 22

 24 omega   96.00  148.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   76.0000  174.0776 26

 25 omega   63.00   89.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   48.0000  168.7307 13

 26 omega   61.00  111.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   55.0000  -45.5361 25

 27 omega  111.00  137.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   71.0000   45.7548 13

 28 omega   73.00  107.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   71.0000   45.7548 17

 29 omega   49.00  135.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -61.0000    0.0000 43

 30 omega   87.00  177.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000    0.0000 45

 31 omega  120.00  176.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000 -150.0000 28

 32 omega   80.00  118.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000 -150.0000 19

 33 omega   84.00  120.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000   90.0000 18

 34 omega   88.00  140.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000  -60.0000 26

 35 omega   50.00   96.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -94.0000  -90.0000 23

 36 omega   83.00  177.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000  -60.0000 47

 37 omega   81.00  107.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000 -120.0000 13

 38 omega   84.00  178.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000   30.0000 47

 39 omega   80.00  172.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000  150.0000 46

 40 omega   78.00  108.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000 -125.0000  150.0000 15

 41 omega   89.00  115.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   45.0000  -90.0000 13

 42 omega   77.00  105.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -94.0000 -150.0000 14

 43 omega   43.00  135.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -61.0000  120.0000 46

 44 omega   30.00   58.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -94.0000 -150.0000 14

 45 omega   44.00  122.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000 -125.0000    0.0000 39

 46 omega   81.00  167.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000  120.0000 43

 47 omega   48.00  108.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -94.0000    0.0000 30

 48 omega   85.00  175.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000  -90.0000 45

 49 omega   80.00  122.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000 -125.0000 -180.0000 21

 50 omega  129.00  175.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000   60.0000 23

 51 omega   81.00  123.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000   60.0000 21

 52 omega  132.00  158.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000  -30.0000 13

 53 omega  124.00  164.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000 -120.0000 20

 54 omega   80.00  120.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000  -30.0000 20

 55 omega   79.00  171.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   80.0000  177.8772 46

 56 omega   86.00  112.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000  -30.0000 13

 57 omega  128.00  154.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000   90.0000 13

 58 omega   84.00  112.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000   60.0000 14

 59 omega   81.00  153.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000   90.0000 36

 60 omega   79.00  105.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   85.0000  -16.6325 13
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1775278000
_diffrn_orient_matrix_UB_12      0.0585967000
_diffrn_orient_matrix_UB_13      -0.0487245000
_diffrn_orient_matrix_UB_21      -0.1305980000
_diffrn_orient_matrix_UB_22      0.1480899000
_diffrn_orient_matrix_UB_23      0.1603348000
_diffrn_orient_matrix_UB_31      0.1088780000
_diffrn_orient_matrix_UB_32      -0.1494228000
_diffrn_orient_matrix_UB_33      0.1143240000
_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  0.0342
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7093
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.827
_diffrn_reflns_theta_min         5.826
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    2.995
_exptl_absorpt_correction_T_max  1.499
_exptl_absorpt_correction_T_min  0.702
_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    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             178
_exptl_crystal_size_max          0.4824
_exptl_crystal_size_mid          0.1558
_exptl_crystal_size_min          0.1068
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0568
_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^)+(0.1101P)^2^+0.3759P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1627
_reflns_number_total             1709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc05751a2.cif
_cod_data_source_block           jsrscc
_cod_original_cell_volume        406.64(11)
_cod_database_code               7115792
_nottingham_internal_coll_name   JSRSCC
_nottingham_internal_coll_number 12536
_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   6/6/2013
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 6/6/2013
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 6/6/2013
_nottingham_internal_refinement_user WL
_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         'C16 H14 S'
_chemical_oxdiff_usercomment
'JSRCCC #12536 IN FOMBLIN FIML ON MICROMOUNT FOR JS/RS'
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelxl_version_number           2013-2