##############################################################################
###                                                                        ###
###        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     SHELXL-97
_journal_date_recd_electronic     2005-10-03
_journal_date_accepted     2005-11-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     12
_journal_page_first     o4374
_journal_page_last     o4375
_journal_paper_category     EO
_journal_coeditor_code     KP6064
_publ_contact_author_name     'Dr Ping Zhong'
_publ_contact_author_address
;
Department of Chemistry
Wenzhou Normal College
325027 Wenzhou
China
;
_publ_contact_author_email     zhongp0512@163.com
_publ_contact_author_fax     '86 577 8837 3013'
_publ_contact_author_phone     '86 577 8837 3013'
_publ_section_title
;\
5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)-\
1H-pyrazole-3-carbonitrile
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Tang, Riyuan' .
;
Department of Chemistry
Wenzhou Normal College
325027 Wenzhou
People's Republic of China
;
    'Zhong, Ping' .
;
Department of Chemistry
Wenzhou Normal College
325027 Wenzhou
People's Republic of China
;
    'Lin, Qiulian' .
;
Department of Chemistry
Wenzhou Normal College
325027 Wenzhou
People's Republic of China
;
    'Hu, Maolin' .
;
Department of Chemistry
Wenzhou Normal College
325027 Wenzhou
People's Republic of China
;
    'Shi, Qian' .
;
Department of Chemistry
Wenzhou Normal College
325027 Wenzhou
People's Republic of China
;
data_I
_chemical_name_systematic
;
5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-
4-(trifluoromethylsulfanyl)-1H-pyrazole-3-carbonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H4 Cl2 F6 N4 S'
_chemical_formula_sum     'C12 H4 Cl2 F6 N4 S'
_chemical_formula_iupac     'C12 H4 Cl2 F6 N4 S'
_chemical_formula_weight     421.16
_chemical_melting_point     434.0(10)
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.7801(8)
_cell_length_b     12.7006(9)
_cell_length_c     12.1039(9)
_cell_angle_alpha     90.00
_cell_angle_beta     96.9730(10)
_cell_angle_gamma     90.00
_cell_volume     1644.9(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3781
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     25.04
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.29
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.701
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     832
_exptl_absorpt_coefficient_mu     0.587
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.7905
_exptl_absorpt_correction_T_max     0.8866
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8518
_diffrn_reflns_av_R_equivalents     0.0178
_diffrn_reflns_av_sigmaI/netI     0.0198
_diffrn_reflns_theta_min     2.33
_diffrn_reflns_theta_max     25.22
_diffrn_reflns_theta_full     25.22
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_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     2953
_reflns_number_gt     2636
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0527
_refine_ls_R_factor_gt     0.0471
_refine_ls_wR_factor_gt     0.1099
_refine_ls_wR_factor_ref     0.1135
_refine_ls_goodness_of_fit_ref     1.098
_refine_ls_restrained_S_all     1.098
_refine_ls_number_reflns     2953
_refine_ls_number_parameters     277
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.059P)²+0.9497P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.211
_refine_diff_density_min     -0.259
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2002)'
_computing_publication_material     SHELXL97
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Cl1 1.17081(7) 0.08140(6) 0.57001(6) 0.0642(2) Uani d . 1 . . Cl
    Cl2 0.77652(7) 0.31669(7) 0.40429(7) 0.0773(3) Uani d . 1 . . Cl
    S1 1.05416(7) 0.41352(7) 0.84033(6) 0.0664(2) Uani d . 1 . . S
    F1 1.0052(3) 0.60601(19) 0.8706(2) 0.1317(10) Uani d . 1 . . F
    F2 0.852(2) 0.516(2) 0.830(2) 0.128(7) Uani d P 0.50 . . F
    F2' 0.841(2) 0.5160(19) 0.788(2) 0.116(6) Uani d P 0.50 . . F
    F3 0.9607(13) 0.5570(11) 0.7024(10) 0.119(4) Uani d P 0.50 . . F
    F3' 0.9846(13) 0.5642(12) 0.7017(12) 0.116(5) Uani d P 0.50 . . F
    F4 1.0293(15) 0.1466(7) 0.0813(8) 0.120(4) Uani d P 0.50 . . F
    F4' 0.9506(19) 0.1303(13) 0.0777(5) 0.166(7) Uani d P 0.50 . . F
    F5 1.1159(10) 0.0611(16) 0.1334(9) 0.147(6) Uani d P 0.50 . . F
    F5' 1.0824(13) 0.0015(11) 0.1475(7) 0.121(5) Uani d P 0.50 . . F
    F6 0.8933(7) 0.0364(11) 0.1036(7) 0.105(2) Uani d P 0.50 . . F
    F6' 0.9570(19) -0.0224(10) 0.1410(9) 0.157(4) Uani d P 0.50 . . F
    N1 0.7652(3) 0.2128(2) 0.8963(2) 0.0742(8) Uani d . 1 . . N
    N2 0.8823(2) 0.19271(17) 0.64758(18) 0.0528(5) Uani d . 1 . . N
    N3 0.96566(19) 0.23574(17) 0.58307(16) 0.0476(5) Uani d . 1 . . N
    N4 1.1189(2) 0.3691(2) 0.5841(2) 0.0665(7) Uani d D 1 . . N
    C1 0.9642(3) 0.5287(3) 0.8031(3) 0.0764(9) Uani d . 1 . . C
    C2 0.9915(2) 0.3283(2) 0.73624(19) 0.0473(6) Uani d . 1 . . C
    C3 0.8993(2) 0.2506(2) 0.7390(2) 0.0483(6) Uani d . 1 . . C
    C4 1.0329(2) 0.3159(2) 0.63280(19) 0.0461(6) Uani d . 1 . . C
    C5 0.8250(3) 0.2289(2) 0.8273(2) 0.0559(7) Uani d . 1 . . C
    C6 0.9741(2) 0.19387(19) 0.47544(19) 0.0433(5) Uani d . 1 . . C
    C7 1.0653(2) 0.1209(2) 0.45895(19) 0.0439(5) Uani d . 1 . . C
    C8 1.0749(2) 0.0802(2) 0.3545(2) 0.0474(6) Uani d . 1 . . C
    H8 1.1357 0.0305 0.3440 0.057 Uiso calc R 1 . . H
    C9 0.9923(2) 0.1149(2) 0.2663(2) 0.0491(6) Uani d . 1 . . C
    C10 0.9004(2) 0.1872(2) 0.2804(2) 0.0527(6) Uani d . 1 . . C
    H10 0.8452 0.2096 0.2200 0.063 Uiso calc R 1 . . H
    C11 0.8914(2) 0.2260(2) 0.3853(2) 0.0493(6) Uani d . 1 . . C
    C12 1.0025(4) 0.0728(3) 0.1517(3) 0.0709(9) Uani d . 1 . . C
    H4A 1.145(3) 0.347(3) 0.525(2) 0.085 Uiso d D 1 . . H
    H4B 1.144(3) 0.4243(19) 0.615(3) 0.085 Uiso d D 1 . . H
_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
    Cl1 C7 . 1.726(2) yes
    Cl2 C11 . 1.727(3) yes
    S1 C2 . 1.735(3) yes
    S1 C1 . 1.783(4) yes
    F1 C1 . 1.319(4) ?
    F2 F2' . 0.51(5) ?
    F2 C1 . 1.30(2) ?
    F2' C1 . 1.33(2) ?
    F3 C1 . 1.266(11) yes
    F3' C1 . 1.350(12) ?
    F4 F4' . 0.869(16) ?
    F4 C12 . 1.321(8) yes
    F4 F5 . 1.517(15) ?
    F4' C12 . 1.235(9) ?
    F4' F6 . 1.396(16) ?
    F5 F5' . 0.866(12) ?
    F5 C12 . 1.277(10) ?
    F5' C12 . 1.255(8) ?
    F5' F6' . 1.378(13) ?
    F6 F6' . 1.077(13) ?
    F6 C12 . 1.331(7) ?
    F6' C12 . 1.306(8) ?
    N1 C5 . 1.135(3) yes
    N2 C3 . 1.323(3) yes
    N2 N3 . 1.374(3) yes
    N3 C4 . 1.349(3) yes
    N3 C6 . 1.420(3) yes
    N4 C4 . 1.340(3) yes
    N4 H4A . 0.848(18) ?
    N4 H4B . 0.828(18) ?
    C2 C4 . 1.388(3) ?
    C2 C3 . 1.403(4) ?
    C3 C5 . 1.438(3) yes
    C6 C11 . 1.383(4) yes
    C6 C7 . 1.384(3) yes
    C7 C8 . 1.381(3) ?
    C8 C9 . 1.377(4) yes
    C8 H8 . 0.9300 yes
    C9 C10 . 1.377(4) ?
    C9 C12 . 1.503(4) yes
    C10 C11 . 1.376(4) ?
    C10 H10 . 0.9300 ?
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
    C2 S1 C1 . . 100.16(15) yes
    F2' F2 C1 . . 81(5) ?
    F2 F2' C1 . . 76(5) ?
    F4' F4 C12 . . 64.8(9) ?
    F4' F4 F5 . . 113.5(13) ?
    C12 F4 F5 . . 52.9(5) ?
    F4 F4' C12 . . 75.6(10) ?
    F4 F4' F6 . . 130.4(14) ?
    C12 F4' F6 . . 60.4(6) ?
    F5' F5 C12 . . 68.6(10) ?
    F5' F5 F4 . . 117.2(14) ?
    C12 F5 F4 . . 55.6(5) ?
    F5 F5' C12 . . 71.4(9) ?
    F5 F5' F6' . . 127.7(14) ?
    C12 F5' F6' . . 59.2(6) ?
    F6' F6 C12 . . 64.7(6) ?
    F6' F6 F4' . . 114.2(9) ?
    C12 F6 F4' . . 53.8(5) ?
    F6 F6' C12 . . 67.1(8) ?
    F6 F6' F5' . . 116.3(10) ?
    C12 F6' F5' . . 55.7(5) ?
    C3 N2 N3 . . 102.7(2) yes
    C4 N3 N2 . . 113.58(19) yes
    C4 N3 C6 . . 126.99(19) yes
    N2 N3 C6 . . 119.44(19) yes
    C4 N4 H4A . . 122(2) ?
    C4 N4 H4B . . 116(3) ?
    H4A N4 H4B . . 123(3) yes
    F3 C1 F2 . . 111.0(13) yes
    F3 C1 F1 . . 110.7(7) yes
    F2 C1 F1 . . 100.7(13) yes
    F3 C1 F2' . . 89.4(13) ?
    F2 C1 F2' . . 22(2) ?
    F1 C1 F2' . . 115.4(12) ?
    F3 C1 F3' . . 11.5(11) ?
    F2 C1 F3' . . 122.0(13) ?
    F1 C1 F3' . . 103.6(8) ?
    F2' C1 F3' . . 100.7(12) ?
    F3 C1 S1 . . 115.4(7) ?
    F2 C1 S1 . . 109.2(11) ?
    F1 C1 S1 . . 108.8(3) ?
    F2' C1 S1 . . 116.1(10) ?
    F3' C1 S1 . . 111.1(7) ?
    C4 C2 C3 . . 104.4(2) yes
    C4 C2 S1 . . 125.86(19) yes
    C3 C2 S1 . . 129.47(18) yes
    N2 C3 C2 . . 113.4(2) ?
    N2 C3 C5 . . 118.8(2) ?
    C2 C3 C5 . . 127.8(2) ?
    N4 C4 N3 . . 123.2(2) yes
    N4 C4 C2 . . 130.9(2) yes
    N3 C4 C2 . . 105.9(2) ?
    N1 C5 C3 . . 179.0(3) yes
    C11 C6 C7 . . 119.0(2) yes
    C11 C6 N3 . . 120.4(2) yes
    C7 C6 N3 . . 120.6(2) yes
    C8 C7 C6 . . 121.1(2) yes
    C8 C7 Cl1 . . 119.27(19) yes
    C6 C7 Cl1 . . 119.66(18) ?
    C9 C8 C7 . . 118.5(2) ?
    C9 C8 H8 . . 120.7 yes
    C7 C8 H8 . . 120.7 ?
    C10 C9 C8 . . 121.6(2) yes
    C10 C9 C12 . . 119.1(3) yes
    C8 C9 C12 . . 119.3(2) ?
    C11 C10 C9 . . 119.1(2) ?
    C11 C10 H10 . . 120.5 ?
    C9 C10 H10 . . 120.5 ?
    C10 C11 C6 . . 120.7(2) yes
    C10 C11 Cl2 . . 119.6(2) ?
    C6 C11 Cl2 . . 119.70(19) ?
    F4' C12 F5' . . 130.6(6) ?
    F4' C12 F5 . . 107.5(8) ?
    F5' C12 F5 . . 40.0(6) ?
    F4' C12 F6' . . 110.1(8) ?
    F5' C12 F6' . . 65.1(7) ?
    F5 C12 F6' . . 103.4(7) ?
    F4' C12 F4 . . 39.6(8) ?
    F5' C12 F4 . . 106.3(7) ?
    F5 C12 F4 . . 71.4(7) yes
    F6' C12 F4 . . 134.6(6) ?
    F4' C12 F6 . . 65.8(8) ?
    F5' C12 F6 . . 107.8(6) ?
    F5 C12 F6 . . 134.2(6) ?
    F6' C12 F6 . . 48.2(6) yes
    F4 C12 F6 . . 102.5(6) ?
    F4' C12 C9 . . 112.4(5) ?
    F5' C12 C9 . . 114.9(4) ?
    F5 C12 C9 . . 112.3(6) yes
    F6' C12 C9 . . 110.7(4) ?
    F4 C12 C9 . . 112.9(5) ?
    F6 C12 C9 . . 111.6(4) ?
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
    F5 F4 F4' C12 . . . . 21.6(10) ?
    C12 F4 F4' F6 . . . . -27.4(11) ?
    F5 F4 F4' F6 . . . . -6(2) ?
    F4' F4 F5 F5' . . . . 7(2) ?
    C12 F4 F5 F5' . . . . 32.0(12) ?
    F4' F4 F5 C12 . . . . -24.7(11) ?
    F4 F5 F5' C12 . . . . -28.0(10) ?
    C12 F5 F5' F6' . . . . 19.6(13) ?
    F4 F5 F5' F6' . . . . -8(2) ?
    F4 F4' F6 F6' . . . . 6.4(18) ?
    C12 F4' F6 F6' . . . . -24.5(7) ?
    F4 F4' F6 C12 . . . . 30.8(13) ?
    F4' F6 F6' C12 . . . . 21.7(6) ?
    C12 F6 F6' F5' . . . . -27.1(6) ?
    F4' F6 F6' F5' . . . . -5.4(11) ?
    F5 F5' F6' F6 . . . . 9(2) ?
    C12 F5' F6' F6 . . . . 30.6(7) ?
    F5 F5' F6' C12 . . . . -21.7(15) ?
    C3 N2 N3 C4 . . . . 0.8(3) ?
    C3 N2 N3 C6 . . . . -179.5(2) ?
    F2' F2 C1 F3 . . . . 16(6) ?
    F2' F2 C1 F1 . . . . 134(5) ?
    F2' F2 C1 F3' . . . . 20(6) ?
    F2' F2 C1 S1 . . . . -112(5) ?
    F2 F2' C1 F3 . . . . -165(5) ?
    F2 F2' C1 F1 . . . . -52(6) ?
    F2 F2' C1 F3' . . . . -163(5) ?
    F2 F2' C1 S1 . . . . 77(6) ?
    C2 S1 C1 F3 . . . . -50.9(8) ?
    C2 S1 C1 F2 . . . . 74.9(13) ?
    C2 S1 C1 F1 . . . . -176.0(2) ?
    C2 S1 C1 F2' . . . . 51.7(13) ?
    C2 S1 C1 F3' . . . . -62.6(7) ?
    C1 S1 C2 C4 . . . . 89.0(3) ?
    C1 S1 C2 C3 . . . . -98.0(3) ?
    N3 N2 C3 C2 . . . . -0.7(3) ?
    N3 N2 C3 C5 . . . . 179.2(2) ?
    C4 C2 C3 N2 . . . . 0.4(3) ?
    S1 C2 C3 N2 . . . . -173.8(2) ?
    C4 C2 C3 C5 . . . . -179.5(3) ?
    S1 C2 C3 C5 . . . . 6.3(4) ?
    N2 N3 C4 N4 . . . . -179.7(3) ?
    C6 N3 C4 N4 . . . . 0.7(4) ?
    N2 N3 C4 C2 . . . . -0.6(3) ?
    C6 N3 C4 C2 . . . . 179.8(2) ?
    C3 C2 C4 N4 . . . . 179.1(3) ?
    S1 C2 C4 N4 . . . . -6.4(4) ?
    C3 C2 C4 N3 . . . . 0.1(3) ?
    S1 C2 C4 N3 . . . . 174.58(19) ?
    N2 C3 C5 N1 . . . .  -9E1(2)
                                ?
    C2 C3 C5 N1 . . . .  9E1(2)
                               ?
    C4 N3 C6 C11 . . . . -97.0(3) ?
    N2 N3 C6 C11 . . . . 83.4(3) ?
    C4 N3 C6 C7 . . . . 82.6(3) ?
    N2 N3 C6 C7 . . . . -97.0(3) ?
    C11 C6 C7 C8 . . . . 0.1(4) ?
    N3 C6 C7 C8 . . . . -179.5(2) ?
    C11 C6 C7 Cl1 . . . . 179.00(19) ?
    N3 C6 C7 Cl1 . . . . -0.7(3) ?
    C6 C7 C8 C9 . . . . 0.8(4) ?
    Cl1 C7 C8 C9 . . . . -178.04(19) ?
    C7 C8 C9 C10 . . . . -1.1(4) ?
    C7 C8 C9 C12 . . . . 179.1(3) ?
    C8 C9 C10 C11 . . . . 0.3(4) ?
    C12 C9 C10 C11 . . . . -179.8(3) ?
    C9 C10 C11 C6 . . . . 0.7(4) ?
    C9 C10 C11 Cl2 . . . . 180.0(2) ?
    C7 C6 C11 C10 . . . . -0.9(4) ?
    N3 C6 C11 C10 . . . . 178.8(2) ?
    C7 C6 C11 Cl2 . . . . 179.78(19) ?
    N3 C6 C11 Cl2 . . . . -0.6(3) ?
    F4 F4' C12 F5' . . . . -63.0(16) ?
    F6 F4' C12 F5' . . . . 93.3(10) ?
    F4 F4' C12 F5 . . . . -24.9(13) ?
    F6 F4' C12 F5 . . . . 131.3(6) ?
    F4 F4' C12 F6' . . . . -136.9(11) ?
    F6 F4' C12 F6' . . . . 19.4(7) ?
    F6 F4' C12 F4 . . . . 156.2(12) ?
    F4 F4' C12 F6 . . . . -156.2(12) ?
    F4 F4' C12 C9 . . . . 99.2(10) ?
    F6 F4' C12 C9 . . . . -104.5(6) ?
    F5 F5' C12 F4' . . . . 66.2(17) ?
    F6' F5' C12 F4' . . . . -95.8(11) ?
    F6' F5' C12 F5 . . . . -162.0(14) ?
    F5 F5' C12 F6' . . . . 162.0(14) ?
    F5 F5' C12 F4 . . . . 30.0(13) ?
    F6' F5' C12 F4 . . . . -132.1(7) ?
    F5 F5' C12 F6 . . . . 139.2(11) ?
    F6' F5' C12 F6 . . . . -22.8(7) ?
    F5 F5' C12 C9 . . . . -95.6(12) ?
    F6' F5' C12 C9 . . . . 102.3(5) ?
    F5' F5 C12 F4' . . . . -133.2(12) ?
    F4 F5 C12 F4' . . . . 16.5(9) ?
    F4 F5 C12 F5' . . . . 149.6(13) ?
    F5' F5 C12 F6' . . . . -16.7(13) ?
    F4 F5 C12 F6' . . . . 132.9(6) ?
    F5' F5 C12 F4 . . . . -149.6(13) ?
    F5' F5 C12 F6 . . . . -60.2(16) ?
    F4 F5 C12 F6 . . . . 89.4(10) ?
    F5' F5 C12 C9 . . . . 102.6(11) ?
    F4 F5 C12 C9 . . . . -107.8(6) ?
    F6 F6' C12 F4' . . . . -23.9(8) ?
    F5' F6' C12 F4' . . . . 126.4(7) ?
    F6 F6' C12 F5' . . . . -150.3(8) ?
    F6 F6' C12 F5 . . . . -138.6(8) ?
    F5' F6' C12 F5 . . . . 11.7(9) ?
    F6 F6' C12 F4 . . . . -61.6(12) ?
    F5' F6' C12 F4 . . . . 88.7(11) ?
    F5' F6' C12 F6 . . . . 150.3(8) ?
    F6 F6' C12 C9 . . . . 101.0(6) ?
    F5' F6' C12 C9 . . . . -108.7(5) ?
    F5 F4 C12 F4' . . . . -154.9(13) ?
    F4' F4 C12 F5' . . . . 135.1(11) ?
    F5 F4 C12 F5' . . . . -19.8(8) ?
    F4' F4 C12 F5 . . . . 154.9(13) ?
    F4' F4 C12 F6' . . . . 64.3(15) ?
    F5 F4 C12 F6' . . . . -90.6(11) ?
    F4' F4 C12 F6 . . . . 22.1(11) ?
    F5 F4 C12 F6 . . . . -132.8(6) ?
    F4' F4 C12 C9 . . . . -98.0(11) ?
    F5 F4 C12 C9 . . . . 107.1(6) ?
    F6' F6 C12 F4' . . . . 155.3(8) ?
    F6' F6 C12 F5' . . . . 28.1(8) ?
    F4' F6 C12 F5' . . . . -127.2(7) ?
    F6' F6 C12 F5 . . . . 64.0(12) ?
    F4' F6 C12 F5 . . . . -91.3(11) ?
    F4' F6 C12 F6' . . . . -155.3(8) ?
    F6' F6 C12 F4 . . . . 140.1(7) ?
    F4' F6 C12 F4 . . . . -15.2(7) ?
    F6' F6 C12 C9 . . . . -98.9(6) ?
    F4' F6 C12 C9 . . . . 105.8(5) ?
    C10 C9 C12 F4' . . . . 20.1(13) ?
    C8 C9 C12 F4' . . . . -160.1(13) ?
    C10 C9 C12 F5' . . . . -174.8(10) ?
    C8 C9 C12 F5' . . . . 5.1(11) ?
    C10 C9 C12 F5 . . . . 141.5(10) ?
    C8 C9 C12 F5 . . . . -38.6(11) ?
    C10 C9 C12 F6' . . . . -103.5(12) ?
    C8 C9 C12 F6' . . . . 76.3(12) ?
    C10 C9 C12 F4 . . . . 63.1(9) ?
    C8 C9 C12 F4 . . . . -117.1(8) ?
    C10 C9 C12 F6 . . . . -51.6(8) ?
    C8 C9 C12 F6 . . . . 128.2(8) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N4 H4A N1 4_665 0.848(18) 2.27(2) 3.099(3) 164(3)
