#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/76/2007607.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2007607
loop_
_publ_author_name
'Briggs, Andrew D.'
'Clegg, William'
'Elsegood, Mark R.J.'
'Frampton, Christopher S.'
'Jackson, Richard F.W.'
_publ_section_title
;
 Conformational Variations in Vinylsulfoximines
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1335
_journal_page_last               1341
_journal_paper_doi               10.1107/S0108270198004508
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C23 H23 N O3 S2'
_chemical_formula_sum            'C23 H23 N O3 S2'
_chemical_formula_weight         425.54
_chemical_name_systematic
;
 (E)-S-phenyl-S-(4-phenylbut-1-enyl)-N-(p-tolylsulfonyl)sulfoximine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.968(3)
_cell_length_b                   11.6851(14)
_cell_length_c                   18.509(4)
_cell_measurement_reflns_used    43
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      10.95
_cell_measurement_theta_min      9.79
_cell_volume                     2155.9(8)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1988)'
_computing_data_reduction        'local programs'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Stoe-Siemens diffractometer with Cryostream cooler (Cosier & Glazer, 1986)'
_diffrn_measurement_method       'ω/θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.076
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2243
_diffrn_reflns_theta_full        22.51
_diffrn_reflns_theta_max         22.51
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.298
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.39(14)
_refine_ls_extinction_coef       0.0011(5)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         1987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.083
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0498P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.095
_reflns_number_gt                1342
_reflns_number_total             1987
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1428.cif
_cod_data_source_block           rfwj48
_cod_database_code               2007607
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 1.02379(15) .52927(11) 1.01248(7) .0270(4) Uani d . . . S
O1 1.1445(4) .5175(3) 1.0544(2) .0387(11) Uani d . . . O
O2 .9019(4) .5577(3) 1.0504(2) .0390(11) Uani d . . . O
C1 .9962(6) .3990(4) .9683(2) .0238(13) Uani d . . . C
C2 1.1035(5) .3304(5) .9484(3) .0253(14) Uani d . . . C
H2 1.1927 .3553 .9573 .030 Uiso calc R . . H
C3 1.0810(6) .2261(4) .9156(3) .0311(15) Uani d . . . C
H3 1.1548 .1785 .9032 .037 Uiso calc R . . H
C4 .9510(7) .1903(5) .9007(3) .0348(15) Uani d . . . C
C5 .8459(6) .2598(4) .9207(3) .0302(15) Uani d . . . C
H5 .7567 .2356 .9110 .036 Uiso calc R . . H
C6 .8664(6) .3628(5) .9539(3) .0264(14) Uani d . . . C
H6 .7921 .4092 .9672 .032 Uiso calc R . . H
C7 .9261(7) .0795(5) .8612(3) .0495(19) Uani d . . . C
H7A .9223 .0941 .8091 .074 Uiso calc R . . H
H7B .8407 .0466 .8773 .074 Uiso calc R . . H
H7C .9990 .0257 .8716 .074 Uiso calc R . . H
N1 1.0605(5) .6199(3) .9495(2) .0264(12) Uani d . . . N
S2 .94883(14) .69643(11) .91487(7) .0242(4) Uani d . . . S
O3 .8308(4) .6445(3) .8826(2) .0358(11) Uani d . . . O
C8 1.0362(6) .7752(4) .8492(3) .0245(13) Uani d . . . C
C9 1.1675(5) .8114(5) .8624(3) .0291(14) Uani d . . . C
H9 1.2124 .7905 .9057 .035 Uiso calc R . . H
C10 1.2303(6) .8780(5) .8113(3) .0371(16) Uani d . . . C
H10 1.3198 .9028 .8192 .044 Uiso calc R . . H
C11 1.1644(7) .9093(5) .7485(3) .0371(16) Uani d . . . C
H11 1.2083 .9558 .7136 .045 Uiso calc R . . H
C12 1.0349(6) .8726(5) .7367(3) .0300(14) Uani d . . . C
H12 .9894 .8952 .6939 .036 Uiso calc R . . H
C13 .9703(6) .8035(4) .7862(2) .0266(13) Uani d . . . C
H13 .8822 .7760 .7770 .032 Uiso calc R . . H
C14 .8941(6) .8006(4) .9760(3) .0280(14) Uani d . . . C
H14 .8143 .8415 .9651 .034 Uiso calc R . . H
C15 .9582(6) .8252(4) 1.0363(3) .0293(14) Uani d . . . C
H15 1.0382 .7843 1.0468 .035 Uiso calc R . . H
C16 .9126(6) .9131(4) 1.0889(3) .0365(15) Uani d . . . C
H16A .8964 .8764 1.1363 .044 Uiso calc R . . H
H16B .8267 .9464 1.0721 .044 Uiso calc R . . H
C17 1.0156(5) 1.0085(4) 1.0979(3) .0322(14) Uani d . . . C
H17A 1.1010 .9749 1.1150 .039 Uiso calc R . . H
H17B 1.0326 1.0440 1.0502 .039 Uiso calc R . . H
C18 .9720(6) 1.1003(4) 1.1503(3) .0256(13) Uani d . . . C
C19 .9365(6) 1.0750(5) 1.2216(3) .0354(15) Uani d . . . C
H19 .9384 .9978 1.2377 .042 Uiso calc R . . H
C20 .8987(6) 1.1606(5) 1.2690(3) .0385(16) Uani d . . . C
H20 .8772 1.1422 1.3176 .046 Uiso calc R . . H
C21 .8923(6) 1.2717(5) 1.2460(3) .0385(16) Uani d . . . C
H21 .8663 1.3306 1.2785 .046 Uiso calc R . . H
C22 .9238(6) 1.2977(5) 1.1752(3) .0381(16) Uani d . . . C
H22 .9188 1.3746 1.1589 .046 Uiso calc R . . H
C23 .9621(6) 1.2133(4) 1.1287(3) .0311(14) Uani d . . . C
H23 .9825 1.2327 1.0801 .037 Uiso calc R . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 117.7(2)
O1 S1 N1 105.2(3)
O2 S1 N1 113.0(2)
O1 S1 C1 107.5(2)
O2 S1 C1 107.2(3)
N1 S1 C1 105.6(2)
C2 C1 C6 119.5(5)
C2 C1 S1 120.4(4)
C6 C1 S1 120.1(4)
C3 C2 C1 120.2(5)
C2 C3 C4 120.3(5)
C5 C4 C3 118.6(5)
C5 C4 C7 120.8(6)
C3 C4 C7 120.6(6)
C6 C5 C4 121.8(5)
C5 C6 C1 119.6(6)
S2 N1 S1 120.6(3)
O3 S2 N1 120.4(2)
O3 S2 C14 107.7(3)
N1 S2 C14 110.8(2)
O3 S2 C8 109.6(2)
N1 S2 C8 103.3(3)
C14 S2 C8 103.7(2)
C13 C8 C9 121.5(5)
C13 C8 S2 118.3(4)
C9 C8 S2 120.2(4)
C10 C9 C8 118.5(5)
C9 C10 C11 120.7(5)
C12 C11 C10 119.7(6)
C11 C12 C13 121.0(5)
C8 C13 C12 118.6(5)
C15 C14 S2 123.3(4)
C14 C15 C16 123.9(5)
C15 C16 C17 111.8(5)
C18 C17 C16 113.3(4)
C23 C18 C19 117.1(5)
C23 C18 C17 120.9(5)
C19 C18 C17 121.9(5)
C20 C19 C18 121.0(5)
C21 C20 C19 120.1(6)
C20 C21 C22 119.6(6)
C23 C22 C21 120.3(6)
C22 C23 C18 121.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.439(4) ?
S1 O2 . 1.442(4) ?
S1 N1 . 1.617(4) ?
S1 C1 . 1.750(5) ?
C1 C2 . 1.386(8) ?
C1 C6 . 1.388(8) ?
C2 C3 . 1.380(7) ?
C3 C4 . 1.389(8) ?
C4 C5 . 1.376(8) ?
C4 C7 . 1.507(7) ?
C5 C6 . 1.367(7) ?
N1 S2 . 1.565(4) ?
S2 O3 . 1.452(4) ?
S2 C14 . 1.749(6) ?
S2 C8 . 1.756(5) ?
C8 C13 . 1.379(7) ?
C8 C9 . 1.397(8) ?
C9 C10 . 1.375(7) ?
C10 C11 . 1.385(7) ?
C11 C12 . 1.377(8) ?
C12 C13 . 1.381(7) ?
C14 C15 . 1.317(7) ?
C15 C16 . 1.487(7) ?
C16 C17 . 1.524(7) ?
C17 C18 . 1.510(7) ?
C18 C23 . 1.383(7) ?
C18 C19 . 1.398(7) ?
C19 C20 . 1.383(8) ?
C20 C21 . 1.368(8) ?
C21 C22 . 1.380(7) ?
C22 C23 . 1.363(8) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 S1 C1 C2 -30.5(5)
O2 S1 C1 C2 -157.8(4)
N1 S1 C1 C2 81.4(4)
O1 S1 C1 C6 148.5(4)
O2 S1 C1 C6 21.2(5)
N1 S1 C1 C6 -99.6(5)
C6 C1 C2 C3 -1.1(7)
S1 C1 C2 C3 177.9(4)
C1 C2 C3 C4 1.6(8)
C2 C3 C4 C5 -1.4(8)
C2 C3 C4 C7 176.6(5)
C3 C4 C5 C6 0.6(8)
C7 C4 C5 C6 -177.4(5)
C4 C5 C6 C1 0.0(8)
C2 C1 C6 C5 0.3(8)
S1 C1 C6 C5 -178.7(4)
O1 S1 N1 S2 -152.5(3)
O2 S1 N1 S2 -22.9(4)
C1 S1 N1 S2 94.0(3)
S1 N1 S2 O3 -55.8(4)
S1 N1 S2 C14 71.1(3)
S1 N1 S2 C8 -178.4(3)
O3 S2 C8 C13 16.9(5)
N1 S2 C8 C13 146.4(4)
C14 S2 C8 C13 -98.0(4)
O3 S2 C8 C9 -165.5(4)
N1 S2 C8 C9 -36.0(5)
C14 S2 C8 C9 79.6(5)
C13 C8 C9 C10 0.9(8)
S2 C8 C9 C10 -176.6(4)
C8 C9 C10 C11 0.6(9)
C9 C10 C11 C12 -0.5(9)
C10 C11 C12 C13 -1.0(8)
C9 C8 C13 C12 -2.3(7)
S2 C8 C13 C12 175.2(4)
C11 C12 C13 C8 2.4(8)
O3 S2 C14 C15 146.6(5)
N1 S2 C14 C15 13.1(5)
C8 S2 C14 C15 -97.2(5)
S2 C14 C15 C16 -179.7(4)
C14 C15 C16 C17 -118.8(6)
C15 C16 C17 C18 179.2(4)
C16 C17 C18 C23 -121.8(6)
C16 C17 C18 C19 56.4(7)
C23 C18 C19 C20 -2.7(9)
C17 C18 C19 C20 179.1(5)
C18 C19 C20 C21 1.7(9)
C19 C20 C21 C22 0.0(9)
C20 C21 C22 C23 -0.5(9)
C21 C22 C23 C18 -0.6(9)
C19 C18 C23 C22 2.2(9)
C17 C18 C23 C22 -179.6(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139056167
