#------------------------------------------------------------------------------
#$Date: 2020-04-02 02:43:20 +0300 (Thu, 02 Apr 2020) $
#$Revision: 249940 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038162.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038162
loop_
_publ_author_name
'Watanabe, Kazuhiro'
'Moriyama, Katsuhiko'
_publ_section_title
;
 C-H Sulfonylation via 1,3-Rearrangement of Sulfonyl Group in N-protected
 3-Bissulfonimidoindole Derivatives Using Fluorine Reagent.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03498
_journal_year                    2020
_chemical_formula_sum            'C22 H20 N2 O4 S2'
_chemical_formula_weight         440.54
_chemical_name_common            u180316mor1
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 114.780(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.963(3)
_cell_length_b                   8.7052(9)
_cell_length_c                   15.5575(15)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      2.95
_cell_volume                     4053.2(7)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13824
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.302
_diffrn_reflns_theta_min         5.292
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    2.663
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0566P)²+3.6684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                3563
_reflns_number_total             3709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03498_si_002.cif
_cod_data_source_block           I
_cod_database_code               4038162
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.13802(2) 0.59310(4) 0.34028(2) 0.02666(12) Uani d . . . 1 . .
S S2 0.06683(2) 1.03610(4) 0.19278(3) 0.02575(12) Uani d . . . 1 . .
O O2 0.14231(4) 0.47364(14) 0.40711(8) 0.0352(3) Uani d . . . 1 . .
C C8 0.01809(5) 0.52054(18) 0.15029(11) 0.0248(3) Uani d . . . 1 . .
C C2 0.05664(5) 0.73560(17) 0.22204(10) 0.0231(3) Uani d . . . 1 . .
C C1 0.08295(5) 0.60739(17) 0.25712(11) 0.0251(3) Uani d . . . 1 . .
C C9 0.16780(5) 0.53090(17) 0.27462(11) 0.0259(3) Uani d . . . 1 . .
C C3 0.01449(5) 0.68209(17) 0.15262(10) 0.0234(3) Uani d . . . 1 . .
C C16 0.10001(5) 0.99657(18) 0.13155(11) 0.0264(3) Uani d . . . 1 . .
C C12 0.21481(5) 0.4311(2) 0.17262(12) 0.0349(4) Uani d . . . 1 . .
C C20 0.16967(6) 1.0144(2) 0.11984(13) 0.0375(4) Uani d . . . 1 . .
H H20 0.2 1.0469 0.1454 0.045 Uiso calc U . R 1 . .
C C7 -0.01716(6) 0.42773(19) 0.09086(12) 0.0314(4) Uani d . . . 1 . .
H H7 -0.0143 0.3192 0.0903 0.038 Uiso calc U . R 1 . .
C C17 0.08123(6) 0.92009(18) 0.04523(11) 0.0293(3) Uani d . . . 1 . .
H H17 0.0508 0.8885 0.0196 0.035 Uiso calc U . R 1 . .
C C14 0.19712(6) 0.4090(2) 0.30815(12) 0.0332(4) Uani d . . . 1 . .
H H14 0.201 0.3587 0.3653 0.04 Uiso calc U . R 1 . .
C C5 -0.06052(5) 0.6606(2) 0.03494(12) 0.0342(4) Uani d . . . 1 . .
H H5 -0.0881 0.7067 -0.0056 0.041 Uiso calc U . R 1 . .
C C4 -0.02624(5) 0.75201(18) 0.09313(11) 0.0288(3) Uani d . . . 1 . .
H H4 -0.0298 0.8603 0.0934 0.035 Uiso calc U . R 1 . .
C C11 0.18484(6) 0.5526(2) 0.14028(12) 0.0358(4) Uani d . . . 1 . .
H H11 0.1802 0.6012 0.0822 0.043 Uiso calc U . R 1 . .
C C18 0.10750(6) 0.89068(19) -0.00286(11) 0.0322(4) Uani d . . . 1 . .
H H18 0.095 0.8374 -0.0615 0.039 Uiso calc U . R 1 . .
C C13 0.22080(6) 0.3609(2) 0.25743(13) 0.0380(4) Uani d . . . 1 . .
H H13 0.2415 0.2785 0.281 0.046 Uiso calc U . R 1 . .
C C10 0.16171(6) 0.6040(2) 0.19069(12) 0.0332(4) Uani d . . . 1 . .
H H10 0.1418 0.6886 0.1683 0.04 Uiso calc U . R 1 . .
C C19 0.15182(6) 0.93779(19) 0.03319(12) 0.0324(4) Uani d . . . 1 . .
C C6 -0.05597(6) 0.5001(2) 0.03366(12) 0.0351(4) Uani d . . . 1 . .
H H6 -0.0805 0.4404 -0.008 0.042 Uiso calc U . R 1 . .
C C21 0.14416(6) 1.0439(2) 0.16935(12) 0.0342(4) Uani d . . . 1 . .
H H21 0.1567 1.096 0.2284 0.041 Uiso calc U . R 1 . .
C C22 0.18009(7) 0.9079(2) -0.01993(14) 0.0413(4) Uani d . . . 1 . .
H H22A 0.1639 0.8403 -0.0739 0.062 Uiso calc U . R 1 . .
H H22B 0.2081 0.8586 0.0223 0.062 Uiso calc U . R 1 . .
H H22C 0.1867 1.0055 -0.0429 0.062 Uiso calc U . R 1 . .
C C15 0.23994(7) 0.3761(3) 0.11687(16) 0.0519(5) Uani d . . . 1 . .
H H15A 0.2653 0.3129 0.1576 0.078 Uiso calc U . R 1 . .
H H15B 0.2508 0.4648 0.0939 0.078 Uiso calc U . R 1 . .
H H15C 0.22 0.3148 0.0628 0.078 Uiso calc U . R 1 . .
N N1 0.05973(4) 0.47722(15) 0.21438(9) 0.0272(3) Uani d . . . 1 . .
H H1 0.0699 0.3824 0.2261 0.033 Uiso calc U . R 1 . .
N N2 0.06873(5) 0.88600(15) 0.25841(10) 0.0270(3) Uani d . . . 1 . .
O O1 0.15200(4) 0.74697(14) 0.37454(8) 0.0369(3) Uani d . . . 1 . .
O O3 0.02195(4) 1.05610(13) 0.12465(8) 0.0331(3) Uani d . . . 1 . .
O O4 0.08821(4) 1.15608(13) 0.26043(8) 0.0329(3) Uani d . . . 1 . .
H H2 0.0907(7) 0.887(2) 0.3055(16) 0.034(5) Uiso d . . . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O1 . . 119.05(7) ?
O2 S1 C1 . . 110.27(7) ?
O1 S1 C1 . . 106.31(7) ?
O2 S1 C9 . . 106.62(7) ?
O1 S1 C9 . . 109.15(7) ?
C1 S1 C9 . . 104.54(7) ?
O3 S2 O4 . . 119.53(7) ?
O3 S2 N2 . . 108.48(7) ?
O4 S2 N2 . . 104.07(7) ?
O3 S2 C16 . . 107.97(7) ?
O4 S2 C16 . . 108.22(7) ?
N2 S2 C16 . . 108.09(7) ?
N1 C8 C7 . . 128.60(14) ?
N1 C8 C3 . . 108.96(13) ?
C7 C8 C3 . . 122.43(14) ?
C1 C2 N2 . . 124.46(14) ?
C1 C2 C3 . . 106.58(13) ?
N2 C2 C3 . . 128.54(14) ?
N1 C1 C2 . . 110.26(13) ?
N1 C1 S1 . . 119.87(11) ?
C2 C1 S1 . . 129.85(12) ?
C14 C9 C10 . . 120.61(15) ?
C14 C9 S1 . . 119.06(12) ?
C10 C9 S1 . . 120.33(12) ?
C4 C3 C8 . . 118.68(14) ?
C4 C3 C2 . . 135.21(14) ?
C8 C3 C2 . . 106.10(13) ?
C21 C16 C17 . . 121.08(15) ?
C21 C16 S2 . . 119.55(12) ?
C17 C16 S2 . . 119.36(12) ?
C11 C12 C13 . . 118.33(16) ?
C11 C12 C15 . . 120.83(17) ?
C13 C12 C15 . . 120.84(17) ?
C21 C20 C19 . . 121.29(16) ?
C6 C7 C8 . . 117.10(16) ?
C18 C17 C16 . . 118.95(15) ?
C9 C14 C13 . . 119.23(16) ?
C4 C5 C6 . . 121.59(15) ?
C5 C4 C3 . . 118.58(15) ?
C10 C11 C12 . . 121.34(16) ?
C17 C18 C19 . . 121.14(16) ?
C14 C13 C12 . . 121.13(16) ?
C11 C10 C9 . . 119.33(16) ?
C18 C19 C20 . . 118.53(16) ?
C18 C19 C22 . . 121.06(16) ?
C20 C19 C22 . . 120.42(17) ?
C7 C6 C5 . . 121.62(16) ?
C20 C21 C16 . . 119.00(16) ?
C8 N1 C1 . . 108.10(13) ?
C2 N2 S2 . . 123.78(11) ?
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 O2 . 1.4350(12) ?
S1 O1 . 1.4438(12) ?
S1 C1 . 1.7366(16) ?
S1 C9 . 1.7725(16) ?
S2 O3 . 1.4239(12) ?
S2 O4 . 1.4401(12) ?
S2 N2 . 1.6433(14) ?
S2 C16 . 1.7595(16) ?
C8 N1 . 1.369(2) ?
C8 C7 . 1.399(2) ?
C8 C3 . 1.413(2) ?
C2 C1 . 1.378(2) ?
C2 N2 . 1.4156(19) ?
C2 C3 . 1.434(2) ?
C1 N1 . 1.373(2) ?
C9 C14 . 1.382(2) ?
C9 C10 . 1.389(2) ?
C3 C4 . 1.410(2) ?
C16 C21 . 1.384(2) ?
C16 C17 . 1.390(2) ?
C12 C11 . 1.390(3) ?
C12 C13 . 1.391(3) ?
C12 C15 . 1.507(3) ?
C20 C21 . 1.382(3) ?
C20 C19 . 1.394(3) ?
C7 C6 . 1.368(2) ?
C17 C18 . 1.385(2) ?
C14 C13 . 1.387(3) ?
C5 C4 . 1.368(2) ?
C5 C6 . 1.407(3) ?
C11 C10 . 1.378(3) ?
C18 C19 . 1.390(3) ?
C19 C22 . 1.505(2) ?
