##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2008-12-11
_journal_date_accepted     2009-01-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      2
_journal_page_first     o360
_journal_page_last     o360
_journal_paper_category     QO
_journal_coeditor_code     PV2130
_publ_contact_author_name     'Dr Charles D. Loftin'
_publ_contact_author_address
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington, KY 40536
USA
;
_publ_contact_author_email     'cdloft2@uky.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '8593239832'
_publ_section_title
;
Cyclooxygenase-1-selective inhibitor SC-560
;
loop_
    _publ_author_name
    _publ_author_address
    'Sihui Long'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington, KY 40536
USA
;
    'Kathryn L. Theiss'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington, KY 40536
USA
;
    'Tonglei Li'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington, KY 40536
USA
;
    'Charles D. Loftin'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington, KY 40536
USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)-1<i>H</i>-pyrazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H12 Cl F3 N2 O'
_chemical_formula_sum     'C17 H12 Cl F3 N2 O'
_chemical_formula_iupac     'C17 H12 Cl F3 N2 O'
_chemical_formula_weight     352.74
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_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     15.585(3)
_cell_length_b     7.1671(14)
_cell_length_c     15.789(3)
_cell_angle_alpha     90.00
_cell_angle_beta     116.81(3)
_cell_angle_gamma     90.00
_cell_volume     1574.1(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3880
_cell_measurement_theta_min     1.0
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     90(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.488
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     0.281
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.9459
_exptl_absorpt_correction_T_max     0.9724
_exptl_special_details
;
;
_diffrn_ambient_temperature     90(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     'Nonius KappaCCD'
_diffrn_measurement_method     '\w scans at fixed \c = 55\%'
_diffrn_detector_area_resol_mean     18
_diffrn_reflns_number     6895
_diffrn_reflns_av_R_equivalents     0.0200
_diffrn_reflns_av_sigmaI/netI     0.0299
_diffrn_reflns_theta_min     1.52
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     3608
_reflns_number_gt     3030
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0445
_refine_ls_R_factor_gt     0.0352
_refine_ls_wR_factor_gt     0.0885
_refine_ls_wR_factor_ref     0.0938
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     3608
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.7994P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.004
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.339
_refine_diff_density_min     -0.288
_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'
    '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'
    'F' 'F' 0.0171 0.0103
                         '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'
_computing_data_collection     'COLLECT (Hooft, 1998)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                                'SHELXTL (Sheldrick, 2008) and local procedures'
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
    Cl Cl13 0.06492(3) 0.90044(6) 0.10611(2) 0.02831(12) Uani d . 1 . .
    N N2 0.38203(8) 0.87316(17) 0.67980(8) 0.0188(2) Uani d . 1 . .
    O O20 0.12419(8) 0.14611(15) 0.54981(7) 0.0287(3) Uani d . 1 . .
    F F3 0.56584(7) 1.19886(15) 0.74065(7) 0.0382(3) Uani d . 1 . .
    F F2 0.52162(8) 1.04490(15) 0.83041(6) 0.0443(3) Uani d . 1 . .
    N N1 0.32413(8) 0.81035(16) 0.59070(7) 0.0169(2) Uani d . 1 . .
    C C10 0.14398(10) 0.89725(19) 0.22720(9) 0.0199(3) Uani d . 1 . .
    C C5 0.33171(9) 0.91657(19) 0.52240(9) 0.0171(3) Uani d . 1 . .
    C C18 0.21726(10) 0.3440(2) 0.50702(9) 0.0196(3) Uani d . 1 . .
    H H18 0.2135 0.2529 0.4618 0.023 Uiso calc R 1 . .
    F F1 0.44389(7) 1.28688(15) 0.75784(7) 0.0448(3) Uani d . 1 . .
    C C11 0.10734(10) 0.8619(2) 0.29082(10) 0.0199(3) Uani d . 1 . .
    H H11 0.0408 0.8367 0.2688 0.024 Uiso calc R 1 . .
    C C19 0.26912(9) 0.50583(19) 0.51716(9) 0.0179(3) Uani d . 1 . .
    H H19 0.3033 0.5239 0.4809 0.021 Uiso calc R 1 . .
    C C7 0.26748(10) 0.89925(18) 0.41982(9) 0.0170(3) Uani d . 1 . .
    C C14 0.27105(9) 0.64202(19) 0.58060(9) 0.0173(3) Uani d . 1 . .
    C C16 0.17333(11) 0.4491(2) 0.62713(10) 0.0244(3) Uani d . 1 . .
    H H16 0.1419 0.4285 0.6657 0.029 Uiso calc R 1 . .
    C C6 0.48912(10) 1.1368(2) 0.74825(10) 0.0222(3) Uani d . 1 . .
    C C12 0.16930(10) 0.86393(19) 0.38715(9) 0.0190(3) Uani d . 1 . .
    H H12 0.1449 0.8411 0.4315 0.023 Uiso calc R 1 . .
    C C4 0.39888(9) 1.0532(2) 0.56958(9) 0.0189(3) Uani d . 1 . .
    H H4 0.4216 1.1482 0.5428 0.023 Uiso calc R 1 . .
    C C8 0.30233(10) 0.9337(2) 0.35415(10) 0.0211(3) Uani d . 1 . .
    H H8 0.3689 0.9576 0.3757 0.025 Uiso calc R 1 . .
    C C3 0.42585(9) 1.0204(2) 0.66545(9) 0.0190(3) Uani d . 1 . .
    C C15 0.22267(10) 0.6153(2) 0.63461(10) 0.0222(3) Uani d . 1 . .
    H H15 0.2231 0.7102 0.6768 0.027 Uiso calc R 1 . .
    C C17 0.17048(10) 0.3143(2) 0.56306(10) 0.0217(3) Uani d . 1 . .
    C C9 0.24066(11) 0.9335(2) 0.25715(10) 0.0238(3) Uani d . 1 . .
    H H9 0.2645 0.9578 0.2124 0.029 Uiso calc R 1 . .
    C C21 0.07544(14) 0.1110(3) 0.60633(11) 0.0403(5) Uani d . 1 . .
    H H21A 0.1214 0.1185 0.6737 0.060 Uiso calc R 1 . .
    H H21B 0.0468 -0.0138 0.5921 0.060 Uiso calc R 1 . .
    H H21C 0.0248 0.2043 0.5919 0.060 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl13 0.0288(2) 0.0370(2) 0.01330(17) 0.00223(16) 0.00434(14) 0.00022(14)
    N2 0.0178(6) 0.0216(6) 0.0138(5) -0.0009(5) 0.0044(4) -0.0028(4)
    O20 0.0349(6) 0.0259(6) 0.0258(5) -0.0125(5) 0.0143(5) -0.0024(4)
    F3 0.0326(5) 0.0472(6) 0.0402(5) -0.0209(5) 0.0211(4) -0.0206(5)
    F2 0.0533(6) 0.0441(6) 0.0177(4) -0.0183(5) 0.0001(4) -0.0012(4)
    N1 0.0180(5) 0.0186(6) 0.0126(5) -0.0015(5) 0.0057(4) -0.0014(4)
    C10 0.0238(7) 0.0184(7) 0.0134(6) 0.0030(5) 0.0046(5) 0.0000(5)
    C5 0.0177(6) 0.0180(7) 0.0159(6) 0.0022(5) 0.0080(5) 0.0011(5)
    C18 0.0207(7) 0.0180(7) 0.0178(6) 0.0029(5) 0.0067(5) -0.0008(5)
    F1 0.0342(5) 0.0427(6) 0.0472(6) 0.0054(5) 0.0092(5) -0.0268(5)
    C11 0.0187(6) 0.0189(7) 0.0189(6) 0.0009(5) 0.0059(5) 0.0001(5)
    C19 0.0188(6) 0.0189(7) 0.0170(6) 0.0031(5) 0.0089(5) 0.0019(5)
    C7 0.0200(6) 0.0141(6) 0.0150(6) 0.0016(5) 0.0063(5) 0.0008(5)
    C14 0.0171(6) 0.0177(7) 0.0142(6) -0.0010(5) 0.0045(5) 0.0013(5)
    C16 0.0259(7) 0.0312(8) 0.0191(6) -0.0075(6) 0.0127(6) -0.0023(6)
    C6 0.0208(7) 0.0240(8) 0.0207(7) -0.0022(6) 0.0084(6) -0.0033(6)
    C12 0.0215(7) 0.0192(7) 0.0171(6) 0.0008(5) 0.0093(5) 0.0011(5)
    C4 0.0182(6) 0.0186(7) 0.0189(6) 0.0001(5) 0.0073(5) 0.0009(5)
    C8 0.0199(7) 0.0237(7) 0.0193(7) -0.0004(6) 0.0084(5) 0.0003(5)
    C3 0.0166(6) 0.0195(7) 0.0191(6) 0.0013(5) 0.0066(5) -0.0008(5)
    C15 0.0238(7) 0.0262(8) 0.0172(6) -0.0032(6) 0.0097(6) -0.0044(6)
    C17 0.0204(7) 0.0213(7) 0.0188(6) -0.0037(6) 0.0048(5) 0.0024(5)
    C9 0.0270(7) 0.0280(8) 0.0177(6) 0.0000(6) 0.0113(6) 0.0009(6)
    C21 0.0495(11) 0.0482(11) 0.0253(8) -0.0297(9) 0.0188(8) -0.0057(7)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Cl13 C10 . 1.7461(15) ?
    N2 C3 . 1.3307(18) ?
    N2 N1 . 1.3605(15) ?
    O20 C17 . 1.3714(18) ?
    O20 C21 . 1.4312(19) ?
    F3 C6 . 1.3308(17) ?
    F2 C6 . 1.3345(17) ?
    N1 C5 . 1.3680(17) ?
    N1 C14 . 1.4305(17) ?
    C10 C11 . 1.384(2) ?
    C10 C9 . 1.385(2) ?
    C5 C4 . 1.3807(19) ?
    C5 C7 . 1.4759(18) ?
    C18 C19 . 1.381(2) ?
    C18 C17 . 1.393(2) ?
    C18 H18 . 0.9500 ?
    F1 C6 . 1.3313(18) ?
    C11 C12 . 1.3861(19) ?
    C11 H11 . 0.9500 ?
    C19 C14 . 1.3892(19) ?
    C19 H19 . 0.9500 ?
    C7 C8 . 1.3924(19) ?
    C7 C12 . 1.3998(19) ?
    C14 C15 . 1.383(2) ?
    C16 C17 . 1.385(2) ?
    C16 C15 . 1.393(2) ?
    C16 H16 . 0.9500 ?
    C6 C3 . 1.4884(19) ?
    C12 H12 . 0.9500 ?
    C4 C3 . 1.3962(19) ?
    C4 H4 . 0.9500 ?
    C8 C9 . 1.394(2) ?
    C8 H8 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C9 H9 . 0.9500 ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
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
    C3 N2 N1 . . 103.79(11) ?
    C17 O20 C21 . . 116.75(12) ?
    N2 N1 C5 . . 112.22(11) ?
    N2 N1 C14 . . 118.35(11) ?
    C5 N1 C14 . . 129.25(11) ?
    C11 C10 C9 . . 121.85(13) ?
    C11 C10 Cl13 . . 118.59(11) ?
    C9 C10 Cl13 . . 119.55(11) ?
    N1 C5 C4 . . 106.47(11) ?
    N1 C5 C7 . . 124.14(12) ?
    C4 C5 C7 . . 128.73(12) ?
    C19 C18 C17 . . 120.10(13) ?
    C19 C18 H18 . . 120.0 ?
    C17 C18 H18 . . 120.0 ?
    C10 C11 C12 . . 118.89(13) ?
    C10 C11 H11 . . 120.6 ?
    C12 C11 H11 . . 120.6 ?
    C18 C19 C14 . . 119.66(12) ?
    C18 C19 H19 . . 120.2 ?
    C14 C19 H19 . . 120.2 ?
    C8 C7 C12 . . 119.10(12) ?
    C8 C7 C5 . . 120.19(12) ?
    C12 C7 C5 . . 120.48(12) ?
    C15 C14 C19 . . 120.45(13) ?
    C15 C14 N1 . . 119.79(12) ?
    C19 C14 N1 . . 119.76(12) ?
    C17 C16 C15 . . 119.53(13) ?
    C17 C16 H16 . . 120.2 ?
    C15 C16 H16 . . 120.2 ?
    F3 C6 F1 . . 106.49(12) ?
    F3 C6 F2 . . 106.86(12) ?
    F1 C6 F2 . . 106.06(12) ?
    F3 C6 C3 . . 111.98(12) ?
    F1 C6 C3 . . 112.21(12) ?
    F2 C6 C3 . . 112.80(13) ?
    C11 C12 C7 . . 120.73(13) ?
    C11 C12 H12 . . 119.6 ?
    C7 C12 H12 . . 119.6 ?
    C5 C4 C3 . . 104.46(12) ?
    C5 C4 H4 . . 127.8 ?
    C3 C4 H4 . . 127.8 ?
    C7 C8 C9 . . 120.73(13) ?
    C7 C8 H8 . . 119.6 ?
    C9 C8 H8 . . 119.6 ?
    N2 C3 C4 . . 113.05(12) ?
    N2 C3 C6 . . 118.86(12) ?
    C4 C3 C6 . . 127.88(13) ?
    C14 C15 C16 . . 119.99(13) ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    O20 C17 C16 . . 124.47(13) ?
    O20 C17 C18 . . 115.32(13) ?
    C16 C17 C18 . . 120.21(13) ?
    C10 C9 C8 . . 118.70(13) ?
    C10 C9 H9 . . 120.6 ?
    C8 C9 H9 . . 120.6 ?
    O20 C21 H21A . . 109.5 ?
    O20 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    O20 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
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
    C3 N2 N1 C5 . . . . -0.10(14) ?
    C3 N2 N1 C14 . . . . 175.45(11) ?
    N2 N1 C5 C4 . . . . 0.92(15) ?
    C14 N1 C5 C4 . . . . -174.02(12) ?
    N2 N1 C5 C7 . . . . -170.48(12) ?
    C14 N1 C5 C7 . . . . 14.6(2) ?
    C9 C10 C11 C12 . . . . 0.3(2) ?
    Cl13 C10 C11 C12 . . . . -178.35(11) ?
    C17 C18 C19 C14 . . . . -2.7(2) ?
    N1 C5 C7 C8 . . . . -147.72(14) ?
    C4 C5 C7 C8 . . . . 42.9(2) ?
    N1 C5 C7 C12 . . . . 37.8(2) ?
    C4 C5 C7 C12 . . . . -131.61(15) ?
    C18 C19 C14 C15 . . . . 1.0(2) ?
    C18 C19 C14 N1 . . . . -179.52(12) ?
    N2 N1 C14 C15 . . . . 45.45(17) ?
    C5 N1 C14 C15 . . . . -139.87(14) ?
    N2 N1 C14 C19 . . . . -134.02(13) ?
    C5 N1 C14 C19 . . . . 40.7(2) ?
    C10 C11 C12 C7 . . . . -0.6(2) ?
    C8 C7 C12 C11 . . . . 0.4(2) ?
    C5 C7 C12 C11 . . . . 174.95(13) ?
    N1 C5 C4 C3 . . . . -1.30(15) ?
    C7 C5 C4 C3 . . . . 169.57(13) ?
    C12 C7 C8 C9 . . . . 0.1(2) ?
    C5 C7 C8 C9 . . . . -174.46(13) ?
    N1 N2 C3 C4 . . . . -0.79(15) ?
    N1 N2 C3 C6 . . . . 174.38(12) ?
    C5 C4 C3 N2 . . . . 1.34(16) ?
    C5 C4 C3 C6 . . . . -173.29(13) ?
    F3 C6 C3 N2 . . . . 143.23(13) ?
    F1 C6 C3 N2 . . . . -97.07(16) ?
    F2 C6 C3 N2 . . . . 22.64(18) ?
    F3 C6 C3 C4 . . . . -42.4(2) ?
    F1 C6 C3 C4 . . . . 77.29(18) ?
    F2 C6 C3 C4 . . . . -163.00(14) ?
    C19 C14 C15 C16 . . . . 1.4(2) ?
    N1 C14 C15 C16 . . . . -178.04(12) ?
    C17 C16 C15 C14 . . . . -2.2(2) ?
    C21 O20 C17 C16 . . . . 0.4(2) ?
    C21 O20 C17 C18 . . . . 179.96(14) ?
    C15 C16 C17 O20 . . . . 180.00(13) ?
    C15 C16 C17 C18 . . . . 0.5(2) ?
    C19 C18 C17 O20 . . . . -177.60(12) ?
    C19 C18 C17 C16 . . . . 2.0(2) ?
    C11 C10 C9 C8 . . . . 0.2(2) ?
    Cl13 C10 C9 C8 . . . . 178.84(11) ?
    C7 C8 C9 C10 . . . . -0.4(2) ?