##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'by CrystalStructure 3.7.0'
_journal_date_recd_electronic     2006-08-15
_journal_date_accepted     2006-09-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     o4545
_journal_page_last     o4546
_journal_paper_category     EO
_journal_coeditor_code     WW2047
_publ_contact_author_name     'Xiu-Rong Hu'
_publ_contact_author_address
;
Center of Analysis and Measurement
Zhejiang University
Hangzhou, 310028
P. R. China
;
_publ_contact_author_email     huxiurong@yahoo.com.cn
_publ_section_title
;\
N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenylsulfanyl)-2-\
hydroxy- 2-methylpropionamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Hu, Xiu-Rong'
;
Center of Analysis and Measurement
Zhejiang University
Hangzhou, Zhejiang 310028
People's Republic of China
;
    'Wang, Li-Li'
;
School of Chemical Engineering and Materials
Zhejiang University of Technology
Hangzhou, Zhejiang 310014
People's Republic of China
;
    'Gu, Jian-Ming'
;
Center of Analysis and Measurement
Zhejiang University
Hangzhou, Zhejiang 310028
People's Republic of China
;
data_I
_chemical_name_systematic
;
N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenylsulfanyl)-2-hydroxy-
2-methylpropionamide
;
_chemical_formula_moiety     'C18 H14 F4 N2 O2 S'
_chemical_formula_sum     'C18 H14 F4 N2 O2 S'
_chemical_formula_iupac     'C18 H14 F4 N2 O2 S'
_chemical_formula_weight     398.37
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 '+X,+Y,+Z'
    2 '-X,-Y,-Z'
_cell_length_a     10.136(5)
_cell_length_b     10.343(6)
_cell_length_c     10.524(4)
_cell_angle_alpha     106.82(2)
_cell_angle_beta     116.97(2)
_cell_angle_gamma     95.19(2)
_cell_volume     908.9(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     7424
_cell_measurement_theta_min     3.3
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     296.0(10)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.456
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     408.00
_exptl_absorpt_coefficient_mu     0.233
_exptl_absorpt_correction_type     none
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.00
_diffrn_reflns_number     9009
_diffrn_reflns_av_R_equivalents     0.026
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
    Refinement using all reflections. The weighted
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total     4135
_reflns_number_gt     2814
_reflns_threshold_expression     F²>2σ(F²)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_gt     0.0653
_refine_ls_wR_factor_ref     0.1749
_refine_ls_goodness_of_fit_ref     1.013
_refine_ls_number_reflns     4135
_refine_ls_number_parameters     253
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                               'w = 1/[0.0015Fo² + 3σ(Fo²) + 0.5]/(4Fo²)'
_refine_ls_shift/su_max     0.0000
_refine_diff_density_max     0.31
_refine_diff_density_min     -0.35
_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' 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'H' 'H' 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
    'O' 'O' 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'N' 'N' 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'F' 'F' 0.017 0.010
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'S' 'S' 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
_computing_data_collection     'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement     'PROCESS-AUTO'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al.,  2003)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'CrystalStructure'
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_disorder_assembly
    _atom_site_disorder_group
    S S1 1.05362(9) 0.66265(11) 0.81085(8) 0.0713(2) Uani d . 1.00 . .
    F F1 0.3255(2) 0.0045(2) 0.7624(3) 0.1071(9) Uani d . 1.00 . .
    F F2 0.5424(3) 0.0978(2) 0.9456(2) 0.1414(9) Uani d . 1.00 . .
    F F3 0.5039(4) -0.0695(2) 0.7535(4) 0.1452(15) Uani d . 1.00 . .
    F F41 0.6412(12) 0.5005(16) 0.1544(5) 0.136(4) Uani d P 0.40 . .
    F F42 0.6827(11) 0.5636(12) 0.1553(5) 0.125(2) Uani d P 0.60 . .
    O O1 0.9926(2) 0.66885(18) 1.07295(18) 0.0498(4) Uani d . 1.00 . .
    O O2 0.6598(2) 0.6361(2) 0.73183(19) 0.0501(5) Uani d . 1.00 . .
    N N1 0.7433(2) 0.4881(2) 0.8566(2) 0.0444(5) Uani d . 1.00 . .
    N N2 0.1879(3) -0.1128(2) 0.3768(2) 0.0750(8) Uani d . 1.00 . .
    C C1 0.9806(3) 0.7893(2) 0.9050(2) 0.0511(7) Uani d . 1.00 . .
    C C2 0.8971(2) 0.7284(2) 0.9706(2) 0.0399(6) Uani d . 1.00 . .
    C C3 0.8414(3) 0.8390(3) 1.0513(3) 0.0563(8) Uani d . 1.00 . .
    C C4 0.7544(2) 0.6118(2) 0.8398(2) 0.0394(6) Uani d . 1.00 . .
    C C5 0.6233(2) 0.3660(2) 0.7574(2) 0.0385(5) Uani d . 1.00 . .
    C C6 0.5300(2) 0.3381(2) 0.6010(2) 0.0407(6) Uani d . 1.00 . .
    C C7 0.4200(2) 0.2130(2) 0.5089(2) 0.0417(6) Uani d . 1.00 . .
    C C8 0.3984(2) 0.1153(2) 0.5687(2) 0.0396(6) Uani d . 1.00 . .
    C C9 0.4899(2) 0.1449(2) 0.7264(2) 0.0397(6) Uani d . 1.00 . .
    C C10 0.6005(2) 0.2696(2) 0.8181(2) 0.0401(6) Uani d . 1.00 . .
    C C11 0.9317(3) 0.6279(3) 0.6132(2) 0.0559(8) Uani d . 1.00 . .
    C C12 0.8210(3) 0.5040(4) 0.5210(3) 0.0717(10) Uani d . 1.00 . .
    C C13 0.7309(4) 0.4758(5) 0.3624(4) 0.0963(13) Uani d . 1.00 . .
    C C14 0.7559(5) 0.5720(7) 0.3070(3) 0.1053(18) Uani d . 1.00 . .
    C C15 0.8668(6) 0.6932(6) 0.3956(5) 0.1030(18) Uani d . 1.00 . .
    C C16 0.9555(4) 0.7216(4) 0.5500(4) 0.0758(12) Uani d . 1.00 . .
    C C17 0.2817(3) -0.0134(2) 0.4641(2) 0.0514(7) Uani d . 1.00 . .
    C C18 0.4695(3) 0.0451(2) 0.7974(2) 0.0990(13) Uani d . 1.00 . .
    H H1 0.9107 0.8231 0.8302 0.061 Uiso c R 1.00 . .
    H H2 1.0664 0.8668 0.9878 0.061 Uiso c R 1.00 . .
    H H6 0.5435 0.4071 0.5578 0.049 Uiso c R 1.00 . .
    H H7 0.3553 0.1923 0.3988 0.050 Uiso c R 1.00 . .
    H H10 0.6641 0.2907 0.9284 0.048 Uiso c R 1.00 . .
    H H12 0.8069 0.4371 0.5662 0.086 Uiso c R 1.00 . .
    H H13 0.6518 0.3875 0.2938 0.115 Uiso c R 1.00 . .
    H H15 0.8811 0.7587 0.3490 0.124 Uiso c R 1.00 . .
    H H16 1.0361 0.8093 0.6171 0.091 Uiso c R 1.00 . .
    H H31 0.7912 0.7982 1.0942 0.067 Uiso c R 1.00 . .
    H H32 0.9276 0.9153 1.1319 0.067 Uiso c R 1.00 . .
    H H33 0.7708 0.8728 0.9787 0.067 Uiso c R 1.00 . .
    H H101 1.0521 0.7372 1.1696 0.060 Uiso c R 1.00 . .
    H H111 0.8171 0.4834 0.9375 0.053 Uiso c R 1.00 . .
_geom_special_details
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C1 . . 1.826(3) y
    S1 C11 . . 1.772(2) y
    F1 C18 . . 1.324(4) ?
    F2 C18 . . 1.291(3) ?
    F3 C18 . . 1.283(4) ?
    F41 C14 . . 1.393(6) ?
    F42 C14 . . 1.393(7) ?
    O1 C2 . . 1.422(3) ?
    O2 C4 . . 1.223(3) ?
    N1 C4 . . 1.343(3) y
    N1 C5 . . 1.404(2) y
    N2 C17 . . 1.135(3) ?
    C1 C2 . . 1.508(4) ?
    C2 C3 . . 1.529(4) ?
    C2 C4 . . 1.536(2) ?
    C5 C6 . . 1.397(3) ?
    C5 C10 . . 1.383(4) ?
    C6 C7 . . 1.375(3) ?
    C7 C8 . . 1.385(4) ?
    C8 C9 . . 1.403(3) ?
    C8 C17 . . 1.439(3) y
    C9 C10 . . 1.374(2) ?
    C9 C18 . . 1.488(4) ?
    C11 C12 . . 1.369(4) ?
    C11 C16 . . 1.384(6) ?
    C12 C13 . . 1.411(5) ?
    C13 C14 . . 1.349(9) ?
    C14 C15 . . 1.349(7) ?
    C15 C16 . . 1.373(5) ?
    O1 H101 . . 0.921 ?
    N1 H111 . . 0.860 ?
    C1 H1 . . 0.970 ?
    C1 H2 . . 0.970 ?
    C3 H31 . . 0.960 ?
    C3 H32 . . 0.960 ?
    C3 H33 . . 0.960 ?
    C6 H6 . . 0.980 ?
    C7 H7 . . 0.980 ?
    C10 H10 . . 0.980 ?
    C12 H12 . . 0.980 ?
    C13 H13 . . 0.980 ?
    C15 H15 . . 0.980 ?
    C16 H16 . . 0.980 ?
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    S1 F41 3.582(14) . 2_766 ?
    S1 C13 3.580(5) . 2_766 ?
    S1 C14 3.526(6) . 2_766 ?
    F1 F2 3.280(4) . 2_657 ?
    F1 C3 3.317(5) . 2_667 ?
    F2 F1 3.280(4) . 2_657 ?
    F2 F2 2.838(4) . 2_657 ?
    F2 F3 3.492(6) . 2_657 ?
    F2 C18 3.477(4) . 2_657 ?
    F3 F2 3.492(6) . 2_657 ?
    F3 O2 3.552(4) . 1_545 ?
    F3 C7 3.191(5) . 2_656 ?
    F41 S1 3.582(14) . 2_766 ?
    F41 F41 3.208(12) . 2_665 ?
    F41 F42 3.239(10) . 2_665 ?
    F41 C5 3.484(14) . 2_666 ?
    F41 C10 3.466(9) . 1_554 ?
    F42 F41 3.239(10) . 2_665 ?
    F42 F42 3.433(10) . 2_665 ?
    F42 N1 3.359(9) . 1_554 ?
    O1 O1 3.432(2) . 2_767 ?
    O1 N1 3.167(3) . 2_767 ?
    O1 N2 2.918(2) . 1_666 ?
    O1 C5 3.577(3) . 2_767 ?
    O2 F3 3.552(4) . 1_565 ?
    O2 C6 3.250(3) . 2_666 ?
    O2 C7 3.188(3) . 2_666 ?
    O2 C13 3.599(4) . 2_666 ?
    N1 F42 3.359(9) . 1_556 ?
    N1 O1 3.167(3) . 2_767 ?
    N2 O1 2.918(2) . 1_444 ?
    N2 C3 3.478(3) . 1_444 ?
    C3 F1 3.317(5) . 2_667 ?
    C3 N2 3.478(3) . 1_666 ?
    C5 F41 3.484(14) . 2_666 ?
    C5 O1 3.577(3) . 2_767 ?
    C6 O2 3.250(3) . 2_666 ?
    C6 C13 3.502(6) . 2_666 ?
    C6 C14 3.566(6) . 2_666 ?
    C7 F3 3.191(5) . 2_656 ?
    C7 O2 3.188(3) . 2_666 ?
    C8 C15 3.569(7) . 2_666 ?
    C10 F41 3.466(9) . 1_556 ?
    C10 F42 3.556(12) . 2_666 ?
    C11 C12 3.585(5) . 2_766 ?
    C11 C13 3.597(6) . 2_766 ?
    C12 C11 3.585(5) . 2_766 ?
    C12 C16 3.553(6) . 2_766 ?
    C13 S1 3.580(5) . 2_766 ?
    C13 O2 3.599(4) . 2_666 ?
    C13 C6 3.502(5) . 2_666 ?
    C13 C11 3.597(6) . 2_766 ?
    C14 S1 3.526(6) . 2_766 ?
    C14 C6 3.566(6) . 2_666 ?
    C15 C8 3.569(7) . 2_666 ?
    C16 C12 3.553(6) . 2_766 ?
    C18 F2 3.477(4) . 2_657 ?
    S1 H10 2.795 . 2_767 ?
    S1 H111 3.246 . 2_767 ?
    F1 H15 3.481 . 2_666 ?
    F1 H16 2.845 . 1_445 ?
    F1 H31 2.849 . 2_667 ?
    F1 H32 3.309 . 2_667 ?
    F1 H33 3.259 . 2_667 ?
    F2 H31 3.522 . 2_667 ?
    F2 H33 3.407 . 1_545 ?
    F3 H7 2.728 . 2_656 ?
    F3 H13 3.310 . 2_656 ?
    F3 H33 2.930 . 1_545 ?
    F41 H10 2.833 . 1_554 ?
    F41 H111 3.455 . 1_554 ?
    F42 H10 3.050 . 1_554 ?
    F42 H31 2.927 . 1_554 ?
    F42 H111 3.119 . 1_554 ?
    O1 H10 3.474 . 2_767 ?
    O1 H15 3.491 . 1_556 ?
    O1 H111 2.618 . 2_767 ?
    O2 H6 2.662 . 2_666 ?
    O2 H7 2.516 . 2_666 ?
    O2 H13 3.026 . 2_666 ?
    N1 H101 3.290 . 2_767 ?
    N2 H12 3.575 . 2_656 ?
    N2 H15 3.118 . 1_445 ?
    N2 H31 3.572 . 1_444 ?
    N2 H32 2.845 . 1_444 ?
    N2 H101 1.997 . 1_444 ?
    C1 H2 3.554 . 2_777 ?
    C1 H7 3.527 . 2_666 ?
    C1 H10 3.519 . 2_767 ?
    C1 H32 3.294 . 2_777 ?
    C3 H2 3.296 . 2_777 ?
    C3 H15 3.331 . 1_556 ?
    C4 H7 3.530 . 2_666 ?
    C5 H101 3.372 . 2_767 ?
    C6 H6 3.474 . 2_666 ?
    C7 H1 3.502 . 2_666 ?
    C8 H15 3.566 . 2_666 ?
    C10 H101 3.472 . 2_767 ?
    C11 H7 3.566 . 2_666 ?
    C13 H6 3.471 . 2_666 ?
    C15 H12 3.582 . 2_766 ?
    C15 H31 3.431 . 1_554 ?
    C16 H7 3.574 . 2_666 ?
    C16 H12 3.495 . 2_766 ?
    C17 H32 3.506 . 1_444 ?
    C17 H101 3.069 . 1_444 ?
    H1 C7 3.502 . 2_666 ?
    H1 H2 3.150 . 2_777 ?
    H1 H7 2.629 . 2_666 ?
    H1 H32 2.854 . 2_777 ?
    H2 C1 3.554 . 2_777 ?
    H2 C3 3.296 . 2_777 ?
    H2 H1 3.150 . 2_777 ?
    H2 H2 3.171 . 2_777 ?
    H2 H10 3.216 . 2_767 ?
    H2 H32 2.891 . 2_777 ?
    H2 H33 2.867 . 2_777 ?
    H6 O2 2.662 . 2_666 ?
    H6 C6 3.474 . 2_666 ?
    H6 C13 3.471 . 2_666 ?
    H6 H6 2.577 . 2_666 ?
    H6 H13 3.538 . 2_666 ?
    H7 F3 2.728 . 2_656 ?
    H7 O2 2.516 . 2_666 ?
    H7 C1 3.527 . 2_666 ?
    H7 C4 3.530 . 2_666 ?
    H7 C11 3.566 . 2_666 ?
    H7 C16 3.574 . 2_666 ?
    H7 H1 2.629 . 2_666 ?
    H7 H33 3.400 . 2_666 ?
    H10 S1 2.795 . 2_767 ?
    H10 F41 2.833 . 1_556 ?
    H10 F42 3.050 . 1_556 ?
    H10 O1 3.474 . 2_767 ?
    H10 C1 3.519 . 2_767 ?
    H10 H2 3.216 . 2_767 ?
    H10 H101 3.477 . 2_767 ?
    H12 N2 3.575 . 2_656 ?
    H12 C15 3.582 . 2_766 ?
    H12 C16 3.495 . 2_766 ?
    H12 H101 3.575 . 2_767 ?
    H13 F3 3.310 . 2_656 ?
    H13 O2 3.026 . 2_666 ?
    H13 H6 3.538 . 2_666 ?
    H15 F1 3.481 . 2_666 ?
    H15 O1 3.491 . 1_554 ?
    H15 N2 3.118 . 1_665 ?
    H15 C3 3.331 . 1_554 ?
    H15 C8 3.566 . 2_666 ?
    H15 H31 2.583 . 1_554 ?
    H15 H32 3.324 . 1_554 ?
    H15 H101 3.068 . 1_554 ?
    H16 F1 2.845 . 1_665 ?
    H16 H32 3.130 . 2_777 ?
    H31 F1 2.849 . 2_667 ?
    H31 F2 3.522 . 2_667 ?
    H31 F42 2.927 . 1_556 ?
    H31 N2 3.572 . 1_666 ?
    H31 C15 3.431 . 1_556 ?
    H31 H15 2.583 . 1_556 ?
    H32 F1 3.309 . 2_667 ?
    H32 N2 2.845 . 1_666 ?
    H32 C1 3.294 . 2_777 ?
    H32 C17 3.506 . 1_666 ?
    H32 H1 2.854 . 2_777 ?
    H32 H2 2.891 . 2_777 ?
    H32 H15 3.324 . 1_556 ?
    H32 H16 3.130 . 2_777 ?
    H33 F1 3.259 . 2_667 ?
    H33 F2 3.407 . 1_565 ?
    H33 F3 2.930 . 1_565 ?
    H33 H2 2.867 . 2_777 ?
    H33 H7 3.400 . 2_666 ?
    H101 N1 3.290 . 2_767 ?
    H101 N2 1.997 . 1_666 ?
    H101 C5 3.372 . 2_767 ?
    H101 C10 3.472 . 2_767 ?
    H101 C17 3.069 . 1_666 ?
    H101 H10 3.477 . 2_767 ?
    H101 H12 3.575 . 2_767 ?
    H101 H15 3.068 . 1_556 ?
    H101 H111 2.941 . 2_767 ?
    H111 S1 3.246 . 2_767 ?
    H111 F41 3.455 . 1_556 ?
    H111 F42 3.119 . 1_556 ?
    H111 O1 2.618 . 2_767 ?
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 S1 C11 . . . 103.32(15) ?
    C4 N1 C5 . . . 127.09(19) ?
    S1 C1 C2 . . . 112.9(2) ?
    O1 C2 C1 . . . 110.5(2) ?
    O1 C2 C3 . . . 110.8(2) ?
    O1 C2 C4 . . . 108.0(2) ?
    C1 C2 C3 . . . 111.0(2) ?
    C1 C2 C4 . . . 109.5(2) ?
    C3 C2 C4 . . . 107.0(2) ?
    O2 C4 N1 . . . 124.81(18) ?
    O2 C4 C2 . . . 119.9(2) ?
    N1 C4 C2 . . . 115.28(19) ?
    N1 C5 C6 . . . 122.3(2) ?
    N1 C5 C10 . . . 118.03(19) ?
    C6 C5 C10 . . . 119.68(19) ?
    C5 C6 C7 . . . 119.2(2) ?
    C6 C7 C8 . . . 121.3(2) ?
    C7 C8 C9 . . . 119.35(19) ?
    C7 C8 C17 . . . 117.7(2) ?
    C9 C8 C17 . . . 122.9(2) ?
    C8 C9 C10 . . . 119.2(2) ?
    C8 C9 C18 . . . 121.7(2) ?
    C10 C9 C18 . . . 119.1(2) ?
    C5 C10 C9 . . . 121.2(2) ?
    S1 C11 C12 . . . 119.9(3) ?
    S1 C11 C16 . . . 119.9(2) ?
    C12 C11 C16 . . . 120.0(2) ?
    C11 C12 C13 . . . 118.8(4) ?
    C12 C13 C14 . . . 119.0(3) ?
    F41 C14 C13 . . . 97.4(7) ?
    F41 C14 C15 . . . 139.7(8) ?
    F42 C14 C13 . . . 128.1(6) ?
    F42 C14 C15 . . . 108.9(7) ?
    C13 C14 C15 . . . 123.0(3) ?
    C14 C15 C16 . . . 118.6(6) ?
    C11 C16 C15 . . . 120.7(3) ?
    N2 C17 C8 . . . 177.1(3) ?
    F1 C18 F2 . . . 102.8(3) ?
    F1 C18 F3 . . . 104.1(2) ?
    F1 C18 C9 . . . 112.6(2) ?
    F2 C18 F3 . . . 108.7(3) ?
    F2 C18 C9 . . . 113.8(2) ?
    F3 C18 C9 . . . 113.9(3) ?
    C2 O1 H101 . . . 109.4 ?
    C4 N1 H111 . . . 116.5 ?
    C5 N1 H111 . . . 116.4 ?
    S1 C1 H1 . . . 108.5 ?
    S1 C1 H2 . . . 108.5 ?
    C2 C1 H1 . . . 108.8 ?
    C2 C1 H2 . . . 108.7 ?
    H1 C1 H2 . . . 109.5 ?
    C2 C3 H31 . . . 109.3 ?
    C2 C3 H32 . . . 109.4 ?
    C2 C3 H33 . . . 109.7 ?
    H31 C3 H32 . . . 109.5 ?
    H31 C3 H33 . . . 109.5 ?
    H32 C3 H33 . . . 109.5 ?
    C5 C6 H6 . . . 120.1 ?
    C7 C6 H6 . . . 120.7 ?
    C6 C7 H7 . . . 119.5 ?
    C8 C7 H7 . . . 119.2 ?
    C5 C10 H10 . . . 119.5 ?
    C9 C10 H10 . . . 119.3 ?
    C11 C12 H12 . . . 119.5 ?
    C13 C12 H12 . . . 121.7 ?
    C12 C13 H13 . . . 120.4 ?
    C14 C13 H13 . . . 120.6 ?
    C14 C15 H15 . . . 119.6 ?
    C16 C15 H15 . . . 121.8 ?
    C11 C16 H16 . . . 119.1 ?
    C15 C16 H16 . . . 120.2 ?
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
    C1 S1 C11 C12 . . . . -105.5(3) ?
    C1 S1 C11 C16 . . . . 79.1(3) ?
    C11 S1 C1 C2 . . . . 108.02(19) ?
    F42 F41 C14 C13 . . . . -175.1(14) ?
    F42 F41 C14 C15 . . . . 4(2) ?
    F41 F42 C14 C13 . . . . 6.2(18) ?
    F41 F42 C14 C15 . . . . -177.0(14) ?
    C4 N1 C5 C6 . . . . 26.2(4) ?
    C4 N1 C5 C10 . . . . -155.3(3) ?
    C5 N1 C4 O2 . . . . -0.9(5) ?
    C5 N1 C4 C2 . . . . 177.9(2) ?
    S1 C1 C2 O1 . . . . 55.44(19) ?
    S1 C1 C2 C3 . . . . 178.70(15) ?
    S1 C1 C2 C4 . . . . -63.4(2) ?
    O1 C2 C4 O2 . . . . -175.2(2) ?
    O1 C2 C4 N1 . . . . 5.9(3) ?
    C1 C2 C4 O2 . . . . -54.9(3) ?
    C1 C2 C4 N1 . . . . 126.3(2) ?
    C3 C2 C4 O2 . . . . 65.5(3) ?
    C3 C2 C4 N1 . . . . -113.3(3) ?
    N1 C5 C6 C7 . . . . 176.4(2) ?
    N1 C5 C10 C9 . . . . -176.9(2) ?
    C6 C5 C10 C9 . . . . 1.6(4) ?
    C10 C5 C6 C7 . . . . -2.0(4) ?
    C5 C6 C7 C8 . . . . 1.1(4) ?
    C6 C7 C8 C9 . . . . 0.3(4) ?
    C6 C7 C8 C17 . . . . -179.5(2) ?
    C7 C8 C9 C10 . . . . -0.8(4) ?
    C7 C8 C9 C18 . . . . 178.7(2) ?
    C17 C8 C9 C10 . . . . 179.0(2) ?
    C17 C8 C9 C18 . . . . -1.5(4) ?
    C8 C9 C10 C5 . . . . -0.2(4) ?
    C8 C9 C18 F1 . . . . -51.7(4) ?
    C8 C9 C18 F2 . . . . -168.1(3) ?
    C8 C9 C18 F3 . . . . 66.6(3) ?
    C10 C9 C18 F1 . . . . 127.8(2) ?
    C10 C9 C18 F2 . . . . 11.4(4) ?
    C10 C9 C18 F3 . . . . -114.0(3) ?
    C18 C9 C10 C5 . . . . -179.7(2) ?
    S1 C11 C12 C13 . . . . -176.7(3) ?
    S1 C11 C16 C15 . . . . 176.8(4) ?
    C12 C11 C16 C15 . . . . 1.4(7) ?
    C16 C11 C12 C13 . . . . -1.2(6) ?
    C11 C12 C13 C14 . . . . -0.4(7) ?
    C12 C13 C14 F41 . . . . -178.3(7) ?
    C12 C13 C14 F42 . . . . 178.5(8) ?
    C12 C13 C14 C15 . . . . 2.0(9) ?
    F41 C14 C15 C16 . . . . 178.7(11) ?
    F42 C14 C15 C16 . . . . -178.9(7) ?
    C13 C14 C15 C16 . . . . -1.9(10) ?
    C14 C15 C16 C11 . . . . 0.1(6) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O1 H101 N2 . . 1_666 0.921 1.997 2.918(2) 177.5 yes
    N1 H111 O1 . . 2_767 0.860 2.618 3.167(3) 122.8 yes
