##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_journal_date_recd_electronic     2015-12-17
_journal_date_accepted     2016-01-04
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616000134
_journal_coeditor_code     HB4006
_publ_contact_author_name     'Ilya Efimov'
_publ_contact_author_address
;
Ural Federal University, Mira 19 Ekaterinburg 620002,
Russian Federation
;
_publ_contact_author_email     'aspirant_efimov@mail.ru'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '+79086340314'
_publ_section_title
;\
(E)-N-[Cyclopentyl(morpholin-4-yl)methylidene]-4-\
fluorobenzenesulfonamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Efimov, Ilya' .
;
Ural Federal University, Mira 19 Ekaterinburg 620002,
Russian Federation
;
    'Slepukhin, Pavel' .
;
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy
of Sciences, 20 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
;
    'Beliaev, Nikolai' .
;
Ural Federal University, Mira 19 Ekaterinburg 620002,
Russian Federation
;
    'Bakulev, Vasiliy' .
;
Ural Federal University, Mira 19 Ekaterinburg 620002,
Russian Federation
;
_publ_section_synopsis
;
In the title compound, the bond lengths at the amidine N---C---N grouping are
similar, indicating significant conjugation.
;
_database_code_depnum_ccdc_archive     'CCDC 1445312'
_chemical_name_systematic
;\
(E)-N-[Cyclopentyl(morpholin-4-yl)methylidene]-4-\
fluorobenzenesulfonamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H21 F N2 O3 S'
_chemical_formula_sum     'C16 H21 F N2 O3 S'
_chemical_formula_iupac     'C16 H21 F N2 O3 S'
_chemical_formula_weight     340.41
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_id
    _space_group_symop_operation_xyz
    1 'x, y, z'
    2 '-x, y+1/2, -z+1/2'
    3 '-x, -y, -z'
    4 'x, -y-1/2, z-1/2'
_cell_length_a     11.5613(7)
_cell_length_b     16.4245(13)
_cell_length_c     8.8730(6)
_cell_angle_alpha     90.00
_cell_angle_beta     107.768(6)
_cell_angle_gamma     90.00
_cell_volume     1604.5(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1405
_cell_measurement_theta_min     2.7570
_cell_measurement_theta_max     27.0300
_cell_measurement_temperature     295(2)
_exptl_crystal_description     plank
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.409
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     0.229
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent, 2013)
;
_exptl_absorpt_correction_T_min     0.93936
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details     ?
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Agilent Xcalibur, Eos'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     15.9555
_diffrn_reflns_number     6974
_diffrn_reflns_av_R_equivalents     0.0293
_diffrn_reflns_theta_min     2.23
_diffrn_reflns_theta_max     27.10
_diffrn_reflns_theta_full     27.10
_diffrn_measured_fraction_theta_max     0.9529
_diffrn_measured_fraction_theta_full     0.9529
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3391
_reflns_number_gt     2323
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0778
_refine_ls_R_factor_gt     0.0464
_refine_ls_wR_factor_gt     0.1167
_refine_ls_wR_factor_ref     0.1371
_refine_ls_goodness_of_fit_ref     1.007
_refine_ls_restrained_S_all     1.007
_refine_ls_number_reflns     3391
_refine_ls_number_parameters     221
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.289
_refine_diff_density_min     -0.380
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'F' 'F' 0.0171 0.0103
                         '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'
_computing_data_collection
;
CrysAlisPro (Agilent, 2013)
;
_computing_cell_refinement
;
CrysAlisPro (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlisPro (Agilent, 2013)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2008)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.26452(5) 0.09127(4) 0.07277(6) 0.04217(19) Uani d . 1 1 . .
    N N2 0.45896(15) 0.09749(12) -0.20031(19) 0.0369(4) Uani d . 1 1 . .
    N N1 0.37106(15) 0.10138(13) -0.0054(2) 0.0413(5) Uani d . 1 1 . .
    C C1 0.14033(18) 0.14851(14) -0.0468(2) 0.0347(5) Uani d . 1 1 . .
    C C7 0.36523(18) 0.07661(14) -0.1498(2) 0.0352(5) Uani d . 1 1 . .
    O O1 0.22350(16) 0.00860(11) 0.07573(19) 0.0568(5) Uani d . 1 1 . .
    C C8 0.26032(19) 0.02854(15) -0.2575(2) 0.0381(5) Uani d . 1 1 B .
    O O3 0.60684(14) 0.19090(11) -0.33829(19) 0.0528(5) Uani d . 1 1 . .
    F F8 -0.14638(14) 0.28150(12) -0.3150(2) 0.0788(5) Uani d . 1 1 . .
    C C2 0.1600(2) 0.22178(15) -0.1115(3) 0.0444(6) Uani d . 1 1 . .
    H H2 0.2388 0.2406 -0.0946 0.053 Uiso calc R 1 1 . .
    O O2 0.30637(15) 0.13122(13) 0.22357(18) 0.0605(5) Uani d . 1 1 . .
    C C13 0.4793(2) 0.07269(15) -0.3481(2) 0.0419(6) Uani d . 1 1 . .
    H H13A 0.4078 0.0450 -0.4148 0.050 Uiso calc R 1 1 . .
    H H13B 0.5472 0.0351 -0.3259 0.050 Uiso calc R 1 1 . .
    C C3 0.0632(2) 0.26682(16) -0.2006(3) 0.0523(6) Uani d . 1 1 . .
    H H3 0.0754 0.3165 -0.2437 0.063 Uiso calc R 1 1 . .
    C C4 -0.0514(2) 0.23724(17) -0.2248(3) 0.0498(6) Uani d . 1 1 . .
    C C16 0.56120(19) 0.14650(16) -0.1027(3) 0.0437(6) Uani d . 1 1 . .
    H H16A 0.6336 0.1130 -0.0675 0.052 Uiso calc R 1 1 . .
    H H16B 0.5425 0.1665 -0.0099 0.052 Uiso calc R 1 1 . .
    C C14 0.5058(2) 0.14643(17) -0.4328(3) 0.0489(6) Uani d . 1 1 . .
    H H14A 0.5216 0.1293 -0.5292 0.059 Uiso calc R 1 1 . .
    H H14B 0.4350 0.1815 -0.4621 0.059 Uiso calc R 1 1 . .
    C C5 -0.0748(2) 0.16534(17) -0.1626(3) 0.0503(6) Uani d . 1 1 . .
    H H5 -0.1541 0.1472 -0.1801 0.060 Uiso calc R 1 1 . .
    C C9 0.1918(2) 0.06850(17) -0.4184(3) 0.0490(6) Uani d . 1 1 B .
    H H9A 0.1177 0.0946 -0.4135 0.059 Uiso calc R 1 1 . .
    H H9B 0.2424 0.1088 -0.4477 0.059 Uiso calc R 1 1 . .
    C C6 0.0229(2) 0.12052(15) -0.0730(3) 0.0446(6) Uani d . 1 1 . .
    H H6 0.0097 0.0711 -0.0298 0.053 Uiso calc R 1 1 . .
    C C12 0.2895(2) -0.05923(15) -0.2949(3) 0.0490(6) Uani d . 1 1 . .
    H H12A 0.3680 -0.0622 -0.3131 0.059 Uiso calc PR 0.75 1 A 1
    H H12B 0.2890 -0.0960 -0.2096 0.059 Uiso calc PR 0.75 1 A 1
    H H12C 0.2512 -0.0983 -0.2434 0.059 Uiso calc PR 0.25 1 A 2
    H H12D 0.3765 -0.0687 -0.2607 0.059 Uiso calc PR 0.25 1 A 2
    C C15 0.5838(2) 0.21732(16) -0.1983(3) 0.0509(6) Uani d . 1 1 . .
    H H15A 0.5135 0.2529 -0.2260 0.061 Uiso calc R 1 1 . .
    H H15B 0.6528 0.2484 -0.1346 0.061 Uiso calc R 1 1 . .
    C C11 0.1861(5) -0.0793(3) -0.4464(5) 0.0564(12) Uani d P 0.75 1 B 1
    H H11A 0.2104 -0.1217 -0.5066 0.068 Uiso calc PR 0.75 1 B 1
    H H11B 0.1141 -0.0970 -0.4213 0.068 Uiso calc PR 0.75 1 B 1
    C C10 0.1633(3) -0.0017(2) -0.5361(3) 0.0769(10) Uani d . 1 1 . .
    H H10A 0.0791 0.0011 -0.6013 0.092 Uiso calc PR 0.75 1 B 1
    H H10B 0.2143 0.0016 -0.6047 0.092 Uiso calc PR 0.75 1 B 1
    H H10C 0.0791 -0.0179 -0.5574 0.092 Uiso calc PR 0.25 1 B 2
    H H10D 0.1749 0.0157 -0.6350 0.092 Uiso calc PR 0.25 1 B 2
    H H8 0.2026(19) 0.0260(13) -0.203(2) 0.032(5) Uiso d . 1 1 . .
    C C11A 0.2368(14) -0.0656(11) -0.477(2) 0.067(4) Uani d PU 0.25 1 B 2
    H H11C 0.3027 -0.0669 -0.5232 0.081 Uiso calc PR 0.25 1 B 2
    H H11D 0.1912 -0.1159 -0.5047 0.081 Uiso calc PR 0.25 1 B 2
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N1 . 1.5963(19) ?
    S1 C1 . 1.772(2) ?
    S1 O1 . 1.4412(19) ?
    S1 O2 . 1.4352(17) ?
    N2 C7 . 1.338(3) ?
    N2 C13 . 1.459(3) ?
    N2 C16 . 1.473(3) ?
    N1 C7 . 1.326(3) ?
    C1 C2 . 1.382(3) ?
    C1 C6 . 1.385(3) ?
    C7 C8 . 1.517(3) ?
    C8 C9 . 1.551(3) ?
    C8 C12 . 1.540(3) ?
    C8 H8 . 0.94(2) ?
    O3 C14 . 1.415(3) ?
    O3 C15 . 1.416(3) ?
    F8 C4 . 1.356(3) ?
    C2 H2 . 0.9300 ?
    C2 C3 . 1.373(3) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C13 C14 . 1.505(3) ?
    C3 H3 . 0.9300 ?
    C3 C4 . 1.365(3) ?
    C4 C5 . 1.365(4) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C16 C15 . 1.509(4) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C5 H5 . 0.9300 ?
    C5 C6 . 1.379(3) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C9 C10 . 1.523(4) ?
    C6 H6 . 0.9300 ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C12 H12C . 0.9700 ?
    C12 H12D . 0.9700 ?
    C12 C11 . 1.537(5) ?
    C12 C11A . 1.545(17) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C11 C10 . 1.483(5) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C10 H10C . 0.9700 ?
    C10 H10D . 0.9700 ?
    C10 C11A . 1.353(17) ?
    C11A H11C . 0.9700 ?
    C11A H11D . 0.9700 ?
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
    N1 S1 C1 . . 106.04(10) ?
    O1 S1 N1 . . 114.06(11) ?
    O1 S1 C1 . . 107.44(10) ?
    O2 S1 N1 . . 105.80(10) ?
    O2 S1 C1 . . 107.26(11) ?
    O2 S1 O1 . . 115.66(12) ?
    C7 N2 C13 . . 126.79(18) ?
    C7 N2 C16 . . 121.98(18) ?
    C13 N2 C16 . . 111.13(17) ?
    C7 N1 S1 . . 124.71(16) ?
    C2 C1 S1 . . 120.31(16) ?
    C2 C1 C6 . . 119.8(2) ?
    C6 C1 S1 . . 119.90(18) ?
    N2 C7 C8 . . 119.76(18) ?
    N1 C7 N2 . . 115.94(19) ?
    N1 C7 C8 . . 124.3(2) ?
    C7 C8 C9 . . 116.42(19) ?
    C7 C8 C12 . . 115.96(18) ?
    C7 C8 H8 . . 105.0(12) ?
    C9 C8 H8 . . 104.4(12) ?
    C12 C8 C9 . . 106.34(18) ?
    C12 C8 H8 . . 107.9(14) ?
    C14 O3 C15 . . 109.61(17) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 C1 . . 120.0(2) ?
    C3 C2 H2 . . 120.0 ?
    N2 C13 H13A . . 109.7 ?
    N2 C13 H13B . . 109.7 ?
    N2 C13 C14 . . 109.7(2) ?
    H13A C13 H13B . . 108.2 ?
    C14 C13 H13A . . 109.7 ?
    C14 C13 H13B . . 109.7 ?
    C2 C3 H3 . . 120.6 ?
    C4 C3 C2 . . 118.7(2) ?
    C4 C3 H3 . . 120.6 ?
    F8 C4 C3 . . 118.3(3) ?
    F8 C4 C5 . . 118.5(2) ?
    C3 C4 C5 . . 123.2(2) ?
    N2 C16 H16A . . 109.7 ?
    N2 C16 H16B . . 109.7 ?
    N2 C16 C15 . . 109.63(18) ?
    H16A C16 H16B . . 108.2 ?
    C15 C16 H16A . . 109.7 ?
    C15 C16 H16B . . 109.7 ?
    O3 C14 C13 . . 112.12(18) ?
    O3 C14 H14A . . 109.2 ?
    O3 C14 H14B . . 109.2 ?
    C13 C14 H14A . . 109.2 ?
    C13 C14 H14B . . 109.2 ?
    H14A C14 H14B . . 107.9 ?
    C4 C5 H5 . . 121.1 ?
    C4 C5 C6 . . 117.8(2) ?
    C6 C5 H5 . . 121.1 ?
    C8 C9 H9A . . 110.8 ?
    C8 C9 H9B . . 110.8 ?
    H9A C9 H9B . . 108.9 ?
    C10 C9 C8 . . 104.7(2) ?
    C10 C9 H9A . . 110.8 ?
    C10 C9 H9B . . 110.8 ?
    C1 C6 H6 . . 119.7 ?
    C5 C6 C1 . . 120.6(2) ?
    C5 C6 H6 . . 119.7 ?
    C8 C12 H12A . . 111.2 ?
    C8 C12 H12B . . 111.2 ?
    C8 C12 H12C . . 110.9 ?
    C8 C12 H12D . . 110.9 ?
    C8 C12 C11A . . 104.3(7) ?
    H12A C12 H12B . . 109.1 ?
    H12A C12 H12C . . 129.0 ?
    H12A C12 H12D . . 27.3 ?
    H12B C12 H12C . . 26.8 ?
    H12B C12 H12D . . 84.7 ?
    H12C C12 H12D . . 108.9 ?
    C11 C12 C8 . . 103.1(2) ?
    C11 C12 H12A . . 111.2 ?
    C11 C12 H12B . . 111.2 ?
    C11 C12 H12C . . 85.7 ?
    C11 C12 H12D . . 134.0 ?
    C11 C12 C11A . . 28.2(5) ?
    C11A C12 H12A . . 85.0 ?
    C11A C12 H12B . . 132.7 ?
    C11A C12 H12C . . 110.9 ?
    C11A C12 H12D . . 110.9 ?
    O3 C15 C16 . . 111.6(2) ?
    O3 C15 H15A . . 109.3 ?
    O3 C15 H15B . . 109.3 ?
    C16 C15 H15A . . 109.3 ?
    C16 C15 H15B . . 109.3 ?
    H15A C15 H15B . . 108.0 ?
    C12 C11 H11A . . 110.9 ?
    C12 C11 H11B . . 110.9 ?
    H11A C11 H11B . . 108.9 ?
    C10 C11 C12 . . 104.4(3) ?
    C10 C11 H11A . . 110.9 ?
    C10 C11 H11B . . 110.9 ?
    C9 C10 H10A . . 110.0 ?
    C9 C10 H10B . . 110.0 ?
    C9 C10 H10C . . 109.7 ?
    C9 C10 H10D . . 109.7 ?
    C11 C10 C9 . . 108.5(3) ?
    C11 C10 H10A . . 110.0 ?
    C11 C10 H10B . . 110.0 ?
    C11 C10 H10C . . 82.6 ?
    C11 C10 H10D . . 133.4 ?
    H10A C10 H10B . . 108.4 ?
    H10A C10 H10C . . 29.8 ?
    H10A C10 H10D . . 80.6 ?
    H10B C10 H10C . . 131.2 ?
    H10B C10 H10D . . 30.4 ?
    H10C C10 H10D . . 108.2 ?
    C11A C10 C9 . . 110.0(7) ?
    C11A C10 C11 . . 30.3(7) ?
    C11A C10 H10A . . 131.7 ?
    C11A C10 H10B . . 81.7 ?
    C11A C10 H10C . . 109.7 ?
    C11A C10 H10D . . 109.7 ?
    C12 C11A H11C . . 109.5 ?
    C12 C11A H11D . . 109.5 ?
    C10 C11A C12 . . 110.7(11) ?
    C10 C11A H11C . . 109.5 ?
    C10 C11A H11D . . 109.5 ?
    H11C C11A H11D . . 108.1 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    S1 N1 C7 N2 . . . . 173.72(17) ?
    S1 N1 C7 C8 . . . . -5.4(3) ?
    S1 C1 C2 C3 . . . . -178.33(18) ?
    S1 C1 C6 C5 . . . . 178.44(17) ?
    N2 C7 C8 C9 . . . . -59.1(3) ?
    N2 C7 C8 C12 . . . . 67.2(3) ?
    N2 C13 C14 O3 . . . . 57.2(3) ?
    N2 C16 C15 O3 . . . . -57.1(2) ?
    N1 S1 C1 C2 . . . . -37.6(2) ?
    N1 S1 C1 C6 . . . . 143.67(18) ?
    N1 C7 C8 C9 . . . . 120.0(2) ?
    N1 C7 C8 C12 . . . . -113.8(2) ?
    C1 S1 N1 C7 . . . . -62.4(2) ?
    C1 C2 C3 C4 . . . . -0.7(4) ?
    C7 N2 C13 C14 . . . . 129.6(2) ?
    C7 N2 C16 C15 . . . . -129.2(2) ?
    C7 C8 C9 C10 . . . . 141.5(2) ?
    C7 C8 C12 C11 . . . . -159.9(3) ?
    C7 C8 C12 C11A . . . . -130.8(7) ?
    O1 S1 N1 C7 . . . . 55.6(2) ?
    O1 S1 C1 C2 . . . . -159.96(18) ?
    O1 S1 C1 C6 . . . . 21.3(2) ?
    C8 C9 C10 C11 . . . . 12.6(4) ?
    C8 C9 C10 C11A . . . . -19.4(8) ?
    C8 C12 C11 C10 . . . . 36.4(4) ?
    C8 C12 C11A C10 . . . . -12.9(12) ?
    F8 C4 C5 C6 . . . . 179.1(2) ?
    C2 C1 C6 C5 . . . . -0.3(3) ?
    C2 C3 C4 F8 . . . . -179.0(2) ?
    C2 C3 C4 C5 . . . . 1.0(4) ?
    O2 S1 N1 C7 . . . . -176.12(19) ?
    O2 S1 C1 C2 . . . . 75.1(2) ?
    O2 S1 C1 C6 . . . . -103.6(2) ?
    C13 N2 C7 N1 . . . . 174.8(2) ?
    C13 N2 C7 C8 . . . . -6.0(3) ?
    C13 N2 C16 C15 . . . . 54.2(2) ?
    C3 C4 C5 C6 . . . . -0.9(4) ?
    C4 C5 C6 C1 . . . . 0.5(4) ?
    C16 N2 C7 N1 . . . . -1.2(3) ?
    C16 N2 C7 C8 . . . . 177.91(19) ?
    C16 N2 C13 C14 . . . . -54.0(2) ?
    C14 O3 C15 C16 . . . . 59.7(2) ?
    C9 C8 C12 C11 . . . . -28.7(3) ?
    C9 C8 C12 C11A . . . . 0.3(7) ?
    C9 C10 C11A C12 . . . . 20.5(12) ?
    C6 C1 C2 C3 . . . . 0.4(4) ?
    C12 C8 C9 C10 . . . . 10.5(3) ?
    C12 C11 C10 C9 . . . . -30.9(4) ?
    C12 C11 C10 C11A . . . . 67.4(15) ?
    C15 O3 C14 C13 . . . . -59.8(3) ?
    C11 C12 C11A C10 . . . . 78.1(15) ?
    C11 C10 C11A C12 . . . . -72.0(15) ?
    C11A C12 C11 C10 . . . . -59.6(15) ?
