##############################################################################
###                                                                        ###
###        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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data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2007-07-30
_journal_date_accepted     2007-08-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      9
_journal_page_first     o3804
_journal_page_last     o3804
_journal_paper_category     QO
_journal_coeditor_code     HG2273
_publ_contact_author_name     'Chang-Sheng Yao'
_publ_contact_author_address
;
Department of Chemistry, Xuzhou Normal University
Xuzhou 221116
People's Republic of China
and Key Laboratory of Biotechnology for Medical Plants of Jiangsu Province
Xuzhou 221116
People's Republic of China
;
_publ_contact_author_email     chxiayu@xznu.edu.cn
_publ_contact_author_fax     '+86-516-83403164'
_publ_contact_author_phone     '+86-516-85664135'
_publ_section_title
;\
Ethyl
2-anilino-4-(2,4-dichlorophenyl)-6-trifluoromethyl-3,4-dihydropyrimidine-5-\
carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Chen-Xia Yu' .
;
Department of Chemistry, Xuzhou Normal University
Xuzhou 221116
People's Republic of China
and Key Laboratory of Biotechnology for Medical Plants of Jiangsu Province
Xuzhou 221116
People's Republic of China
;
    'Song Lei' .
;
Department of Chemistry, Xuzhou Normal University
Xuzhou 221116
People's Republic of China
and Key Laboratory of Biotechnology for Medical Plants of Jiangsu Province
Xuzhou 221116
People's Republic of China
;
    'Chang-Sheng Yao' .
;
Department of Chemistry, Xuzhou Normal University
Xuzhou 221116
People's Republic of China
and Key Laboratory of Biotechnology for Medical Plants of Jiangsu Province
Xuzhou 221116
People's Republic of China
;
    'Shu-Jiang Tu' .
;
Department of Chemistry, Xuzhou Normal University
Xuzhou 221116
People's Republic of China
and Key Laboratory of Biotechnology for Medical Plants of Jiangsu Province
Xuzhou 221116
People's Republic of China
;
data_I
_chemical_name_systematic
;
Ethyl 2-anilino-4-(2,4-dichlorophenyl)-6-trifluoromethyl-3,4-
dihydropyrimidine-5-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H16 Cl2 F3 N3 O2'
_chemical_formula_sum     'C20 H16 Cl2 F3 N3 O2'
_chemical_formula_iupac     'C20 H16 Cl2 F3 N3 O2'
_chemical_formula_weight     458.26
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     11.0085(15)
_cell_length_b     11.8934(17)
_cell_length_c     15.698(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2055.4(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4124
_cell_measurement_theta_min     2.15
_cell_measurement_theta_max     25.08
_cell_measurement_temperature     294(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.481
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     936
_exptl_absorpt_coefficient_mu     0.365
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9111
_exptl_absorpt_correction_T_max     0.9306
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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 SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11861
_diffrn_reflns_av_R_equivalents     0.0377
_diffrn_reflns_av_sigmaI/netI     0.0400
_diffrn_reflns_theta_min     2.15
_diffrn_reflns_theta_max     26.38
_diffrn_reflns_theta_full     26.38
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_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     4177
_reflns_number_gt     3175
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0596
_refine_ls_R_factor_gt     0.0373
_refine_ls_wR_factor_gt     0.0812
_refine_ls_wR_factor_ref     0.0917
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     4177
_refine_ls_number_parameters     281
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0404P)²+0.3148P] 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     0.212
_refine_diff_density_min     -0.222
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0261(15)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983)'
_refine_ls_abs_structure_Flack     -0.06(6)
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     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1999)'
_computing_publication_material     'SHELXTL'
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 Cl1 0.72705(8) 0.14863(7) -0.12933(5) 0.0766(3) Uani d . 1 . .
    Cl Cl2 0.37002(8) 0.42819(9) -0.22290(5) 0.0887(3) Uani d . 1 . .
    F F1 0.62596(16) 0.48924(14) 0.24705(10) 0.0706(5) Uani d . 1 . .
    F F2 0.80585(16) 0.45551(14) 0.29272(9) 0.0730(5) Uani d . 1 . .
    F F3 0.77062(17) 0.60034(12) 0.21670(10) 0.0757(5) Uani d . 1 . .
    O O1 0.56257(18) 0.19540(17) 0.14384(13) 0.0646(5) Uani d . 1 . .
    O O2 0.64809(17) 0.27081(15) 0.25945(11) 0.0592(5) Uani d . 1 . .
    N N1 0.86238(17) 0.32244(16) 0.00923(13) 0.0432(5) Uani d D 1 . .
    N N2 0.85306(18) 0.48302(16) 0.09472(12) 0.0428(5) Uani d . 1 . .
    N N3 0.9898(2) 0.47054(18) -0.01780(15) 0.0528(5) Uani d D 1 . .
    C C1 0.6315(2) 0.2608(2) -0.10509(15) 0.0456(6) Uani d . 1 . .
    C C2 0.5460(2) 0.2923(3) -0.16446(15) 0.0540(7) Uani d . 1 . .
    H H2 0.5375 0.2527 -0.2152 0.065 Uiso calc R 1 . .
    C C3 0.4732(2) 0.3837(2) -0.14692(16) 0.0525(7) Uani d . 1 . .
    C C4 0.4828(2) 0.4401(2) -0.07171(17) 0.0521(7) Uani d . 1 . .
    H H4 0.4322 0.5008 -0.0601 0.063 Uiso calc R 1 . .
    C C5 0.5684(2) 0.4060(2) -0.01277(16) 0.0461(6) Uani d . 1 . .
    H H5 0.5744 0.4446 0.0386 0.055 Uiso calc R 1 . .
    C C6 0.6455(2) 0.31641(18) -0.02757(14) 0.0381(5) Uani d . 1 . .
    C C7 0.7429(2) 0.28239(17) 0.03625(14) 0.0393(5) Uani d . 1 . .
    H H7 0.7453 0.2001 0.0388 0.047 Uiso calc R 1 . .
    C C8 0.89924(19) 0.42730(19) 0.03061(16) 0.0408(6) Uani d . 1 . .
    C C9 0.7726(2) 0.42650(18) 0.14511(14) 0.0379(5) Uani d . 1 . .
    C C10 0.7207(2) 0.32622(17) 0.12503(14) 0.0388(5) Uani d . 1 . .
    C C11 0.6358(2) 0.2590(2) 0.17605(16) 0.0450(6) Uani d . 1 . .
    C C12 0.5585(3) 0.2171(3) 0.3156(2) 0.0770(10) Uani d . 1 . .
    H H12A 0.5411 0.2663 0.3633 0.092 Uiso calc R 1 . .
    H H12B 0.4835 0.2051 0.2845 0.092 Uiso calc R 1 . .
    C C13 0.6041(3) 0.1095(3) 0.3472(2) 0.0955(12) Uani d . 1 . .
    H H13A 0.6823 0.1203 0.3731 0.143 Uiso calc R 1 . .
    H H13B 0.6114 0.0576 0.3006 0.143 Uiso calc R 1 . .
    H H13C 0.5486 0.0798 0.3887 0.143 Uiso calc R 1 . .
    C C14 0.7432(3) 0.4921(2) 0.22603(15) 0.0491(6) Uani d . 1 . .
    C C15 1.0562(2) 0.5710(2) -0.00892(18) 0.0513(7) Uani d . 1 . .
    C C16 1.1471(3) 0.5888(3) -0.0697(2) 0.0690(8) Uani d . 1 . .
    H H16 1.1620 0.5345 -0.1111 0.083 Uiso calc R 1 . .
    C C17 1.2143(3) 0.6858(3) -0.0688(3) 0.0866(11) Uani d . 1 . .
    H H17 1.2739 0.6971 -0.1099 0.104 Uiso calc R 1 . .
    C C18 1.1946(3) 0.7664(3) -0.0077(3) 0.0902(12) Uani d . 1 . .
    H H18 1.2402 0.8322 -0.0074 0.108 Uiso calc R 1 . .
    C C20 1.0364(3) 0.6516(2) 0.05281(19) 0.0606(7) Uani d . 1 . .
    H H20 0.9767 0.6411 0.0940 0.073 Uiso calc R 1 . .
    C C19 1.1066(3) 0.7487(3) 0.0527(2) 0.0779(10) Uani d . 1 . .
    H H19 1.0937 0.8028 0.0945 0.093 Uiso calc R 1 . .
    H H1A 0.897(2) 0.290(2) -0.0361(11) 0.055(8) Uiso d D 1 . .
    H H3A 1.016(3) 0.426(2) -0.0595(13) 0.067(9) Uiso d D 1 . .
_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 C1 . 1.741(3) ?
    Cl2 C3 . 1.730(3) ?
    F1 C14 . 1.333(3) ?
    F2 C14 . 1.327(3) ?
    F3 C14 . 1.330(3) ?
    O1 C11 . 1.215(3) ?
    O2 C11 . 1.324(3) ?
    O2 C12 . 1.469(3) ?
    N1 C8 . 1.354(3) ?
    N1 C7 . 1.462(3) ?
    N1 H1A . 0.897(10) ?
    N2 C8 . 1.308(3) ?
    N2 C9 . 1.365(3) ?
    N3 C8 . 1.355(3) ?
    N3 C15 . 1.408(3) ?
    N3 H3A . 0.890(10) ?
    C1 C2 . 1.377(4) ?
    C1 C6 . 1.393(3) ?
    C2 C3 . 1.379(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.362(4) ?
    C4 C5 . 1.382(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.381(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.522(3) ?
    C7 C10 . 1.508(3) ?
    C7 H7 . 0.9800 ?
    C9 C10 . 1.360(3) ?
    C9 C14 . 1.526(3) ?
    C10 C11 . 1.468(3) ?
    C12 C13 . 1.462(5) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C15 C20 . 1.381(4) ?
    C15 C16 . 1.399(4) ?
    C16 C17 . 1.371(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.373(5) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.373(5) ?
    C18 H18 . 0.9300 ?
    C20 C19 . 1.389(4) ?
    C20 H20 . 0.9300 ?
    C19 H19 . 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
    C11 O2 C12 . . 118.6(2) ?
    C8 N1 C7 . . 119.86(19) ?
    C8 N1 H1A . . 117.8(17) ?
    C7 N1 H1A . . 118.4(17) ?
    C8 N2 C9 . . 116.66(19) ?
    C8 N3 C15 . . 130.5(2) ?
    C8 N3 H3A . . 115.5(19) ?
    C15 N3 H3A . . 113.9(19) ?
    C2 C1 C6 . . 122.5(2) ?
    C2 C1 Cl1 . . 118.25(19) ?
    C6 C1 Cl1 . . 119.21(19) ?
    C1 C2 C3 . . 118.5(2) ?
    C1 C2 H2 . . 120.8 ?
    C3 C2 H2 . . 120.8 ?
    C4 C3 C2 . . 121.1(2) ?
    C4 C3 Cl2 . . 119.9(2) ?
    C2 C3 Cl2 . . 119.0(2) ?
    C3 C4 C5 . . 119.3(2) ?
    C3 C4 H4 . . 120.4 ?
    C5 C4 H4 . . 120.4 ?
    C6 C5 C4 . . 122.2(2) ?
    C6 C5 H5 . . 118.9 ?
    C4 C5 H5 . . 118.9 ?
    C5 C6 C1 . . 116.4(2) ?
    C5 C6 C7 . . 121.8(2) ?
    C1 C6 C7 . . 121.8(2) ?
    N1 C7 C10 . . 107.54(18) ?
    N1 C7 C6 . . 110.87(18) ?
    C10 C7 C6 . . 113.73(19) ?
    N1 C7 H7 . . 108.2 ?
    C10 C7 H7 . . 108.2 ?
    C6 C7 H7 . . 108.2 ?
    N2 C8 N1 . . 122.8(2) ?
    N2 C8 N3 . . 121.7(2) ?
    N1 C8 N3 . . 115.5(2) ?
    C10 C9 N2 . . 124.8(2) ?
    C10 C9 C14 . . 123.6(2) ?
    N2 C9 C14 . . 111.61(19) ?
    C9 C10 C11 . . 128.3(2) ?
    C9 C10 C7 . . 116.7(2) ?
    C11 C10 C7 . . 114.78(19) ?
    O1 C11 O2 . . 123.1(2) ?
    O1 C11 C10 . . 122.3(2) ?
    O2 C11 C10 . . 114.6(2) ?
    C13 C12 O2 . . 110.7(3) ?
    C13 C12 H12A . . 109.5 ?
    O2 C12 H12A . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    O2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    F2 C14 F3 . . 106.7(2) ?
    F2 C14 F1 . . 107.4(2) ?
    F3 C14 F1 . . 105.8(2) ?
    F2 C14 C9 . . 112.3(2) ?
    F3 C14 C9 . . 110.8(2) ?
    F1 C14 C9 . . 113.5(2) ?
    C20 C15 C16 . . 119.1(3) ?
    C20 C15 N3 . . 125.2(2) ?
    C16 C15 N3 . . 115.6(3) ?
    C17 C16 C15 . . 120.4(3) ?
    C17 C16 H16 . . 119.8 ?
    C15 C16 H16 . . 119.8 ?
    C16 C17 C18 . . 120.7(3) ?
    C16 C17 H17 . . 119.7 ?
    C18 C17 H17 . . 119.7 ?
    C19 C18 C17 . . 119.1(3) ?
    C19 C18 H18 . . 120.4 ?
    C17 C18 H18 . . 120.4 ?
    C15 C20 C19 . . 119.3(3) ?
    C15 C20 H20 . . 120.4 ?
    C19 C20 H20 . . 120.4 ?
    C18 C19 C20 . . 121.4(3) ?
    C18 C19 H19 . . 119.3 ?
    C20 C19 H19 . . 119.3 ?
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
    C6 C1 C2 C3 . . . . 1.4(4) ?
    Cl1 C1 C2 C3 . . . . -177.60(19) ?
    C1 C2 C3 C4 . . . . -1.9(4) ?
    C1 C2 C3 Cl2 . . . . 177.07(19) ?
    C2 C3 C4 C5 . . . . 1.1(4) ?
    Cl2 C3 C4 C5 . . . . -177.8(2) ?
    C3 C4 C5 C6 . . . . 0.2(4) ?
    C4 C5 C6 C1 . . . . -0.7(3) ?
    C4 C5 C6 C7 . . . . 177.5(2) ?
    C2 C1 C6 C5 . . . . -0.1(3) ?
    Cl1 C1 C6 C5 . . . . 178.86(18) ?
    C2 C1 C6 C7 . . . . -178.3(2) ?
    Cl1 C1 C6 C7 . . . . 0.6(3) ?
    C8 N1 C7 C10 . . . . -38.3(3) ?
    C8 N1 C7 C6 . . . . 86.6(2) ?
    C5 C6 C7 N1 . . . . -101.8(3) ?
    C1 C6 C7 N1 . . . . 76.4(3) ?
    C5 C6 C7 C10 . . . . 19.5(3) ?
    C1 C6 C7 C10 . . . . -162.3(2) ?
    C9 N2 C8 N1 . . . . 6.0(3) ?
    C9 N2 C8 N3 . . . . -172.5(2) ?
    C7 N1 C8 N2 . . . . 21.8(3) ?
    C7 N1 C8 N3 . . . . -159.7(2) ?
    C15 N3 C8 N2 . . . . 4.9(4) ?
    C15 N3 C8 N1 . . . . -173.7(2) ?
    C8 N2 C9 C10 . . . . -12.8(3) ?
    C8 N2 C9 C14 . . . . 169.6(2) ?
    N2 C9 C10 C11 . . . . 178.6(2) ?
    C14 C9 C10 C11 . . . . -4.1(4) ?
    N2 C9 C10 C7 . . . . -7.6(3) ?
    C14 C9 C10 C7 . . . . 169.7(2) ?
    N1 C7 C10 C9 . . . . 30.7(3) ?
    C6 C7 C10 C9 . . . . -92.4(2) ?
    N1 C7 C10 C11 . . . . -154.66(19) ?
    C6 C7 C10 C11 . . . . 82.2(2) ?
    C12 O2 C11 O1 . . . . -8.8(4) ?
    C12 O2 C11 C10 . . . . 173.1(2) ?
    C9 C10 C11 O1 . . . . 152.8(3) ?
    C7 C10 C11 O1 . . . . -21.1(3) ?
    C9 C10 C11 O2 . . . . -29.1(3) ?
    C7 C10 C11 O2 . . . . 157.0(2) ?
    C11 O2 C12 C13 . . . . 97.6(3) ?
    C10 C9 C14 F2 . . . . 82.9(3) ?
    N2 C9 C14 F2 . . . . -99.5(2) ?
    C10 C9 C14 F3 . . . . -158.0(2) ?
    N2 C9 C14 F3 . . . . 19.6(3) ?
    C10 C9 C14 F1 . . . . -39.2(3) ?
    N2 C9 C14 F1 . . . . 138.4(2) ?
    C8 N3 C15 C20 . . . . -3.2(4) ?
    C8 N3 C15 C16 . . . . 178.3(3) ?
    C20 C15 C16 C17 . . . . -1.0(4) ?
    N3 C15 C16 C17 . . . . 177.7(3) ?
    C15 C16 C17 C18 . . . . 0.7(5) ?
    C16 C17 C18 C19 . . . . 0.2(6) ?
    C16 C15 C20 C19 . . . . 0.4(4) ?
    N3 C15 C20 C19 . . . . -178.1(3) ?
    C17 C18 C19 C20 . . . . -0.7(5) ?
    C15 C20 C19 C18 . . . . 0.4(5) ?
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
    N3 H3A O1 4 0.890(10) 2.026(12) 2.907(3) 170(3)
    N1 H1A O1 4 0.897(10) 2.490(17) 3.267(3) 145(2)
    N1 H1A Cl1 . 0.897(10) 2.91(2) 3.350(2) 111.8(18)
