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###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# 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.                                        #
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# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-06-05
_journal_date_accepted     2006-06-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      7
_journal_page_first     o2832
_journal_page_last     o2833
_journal_paper_category     EO
_journal_coeditor_code     CF2035
_publ_contact_author_name     'Dr. Ping Zhong'
_publ_contact_author_address
; Department of Chemistry
Wenzhou University
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-(3-Bromobenzylideneamino)-4-chloro-1-[2,6-dichloro-4-
(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Li, Shu-Yan' .
;
Department of Chemistry
Wenzhou University
325027 Wenzhou
People's Republic of China
;
    'Zhong, Ping' .
;
Department of Chemistry
Wenzhou University
325027 Wenzhou
People's Republic of China
;
    'Hu, Mao-Lin' .
;
Department of Chemistry
Wenzhou University
325027 Wenzhou
People's Republic of China
;
data_I
_chemical_name_systematic
;
5-(3-Bromobenzylideneamino)-4-chloro-1-[2,6-dichloro-4-
(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H7 Br Cl3 F3 N4'
_chemical_formula_sum     'C18 H7 Br Cl3 F3 N4'
_chemical_formula_iupac     'C18 H7 Br Cl3 F3 N4'
_chemical_formula_weight     522.54
_chemical_melting_point     '470-471'
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.8683(8)
_cell_length_b     11.5269(12)
_cell_length_c     11.8954(12)
_cell_angle_alpha     92.974(2)
_cell_angle_beta     107.609(2)
_cell_angle_gamma     98.142(2)
_cell_volume     1012.82(18)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1216
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     24.18
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.21
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.713
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     2.464
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.626
_exptl_absorpt_correction_T_max     0.756
_exptl_special_details
;
IR (KBr, ν cm⁻¹): 3419, 2309, 2241, 1621, 1509,
1310; ¹H NMR (C₃D₆O, δ, p.p.m.): 9.39 (s, 1H),
8.15 (s, 2H), 8.01 (s, 1H), 7.88 (d,J = 7.74Hz, 1H),
7.79 (d, J = 8.12Hz, 1H), 7.46 (t, J = 7.86Hz, 1H);
¹³C NMR (C₃D₆O, δ, p.p.m.):
166.1, 145.7, 137.0, 136.2 ,135.5, 133.8 (2C), 131.9 (2C),
131.0, 128.4(2C), 127.1 (2C),
126.3, 122.6, 110.8, 103.4.
;
_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     5472
_diffrn_reflns_av_R_equivalents     0.0195
_diffrn_reflns_av_sigmaI/netI     0.0490
_diffrn_reflns_theta_min     1.79
_diffrn_reflns_theta_max     25.26
_diffrn_reflns_theta_full     25.26
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.982
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_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     3614
_reflns_number_gt     2463
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0872
_refine_ls_R_factor_gt     0.0585
_refine_ls_wR_factor_gt     0.1365
_refine_ls_wR_factor_ref     0.1526
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.044
_refine_ls_number_reflns     3614
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0721P)²+0.403P] 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     0.672
_refine_diff_density_min     -0.466
_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'
    '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'
    'Br' 'Br' -0.2901 2.4595
                         '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_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
    Br Br1 1.12268(8) 1.05634(6) 0.80614(6) 0.0885(3) Uani d . 1 . .
    Cl Cl1 0.1425(2) 0.77826(16) 0.08115(17) 0.0935(6) Uani d . 1 . .
    Cl Cl2 0.69753(18) 0.53816(13) 0.19242(13) 0.0698(4) Uani d . 1 . .
    Cl Cl3 0.2776(2) 0.57684(13) 0.51239(12) 0.0793(5) Uani d . 1 . .
    F F1 0.7760(6) 0.8138(6) -0.1287(4) 0.161(2) Uani d . 1 . .
    F F2 0.5323(8) 0.7531(5) -0.2480(3) 0.172(3) Uani d . 1 . .
    F F3 0.5789(10) 0.9122(5) -0.1609(6) 0.185(3) Uani d . 1 . .
    N N1 0.3540(5) 0.6074(3) 0.2102(3) 0.0486(9) Uani d . 1 . .
    N N2 0.2331(5) 0.5069(3) 0.1792(3) 0.0527(10) Uani d . 1 . .
    N N3 -0.0468(7) 0.3150(4) 0.2878(5) 0.0794(14) Uani d . 1 . .
    N N4 0.5036(5) 0.7593(3) 0.3613(3) 0.0506(10) Uani d . 1 . .
    C C1 0.6069(8) 0.8080(6) -0.1458(5) 0.0688(15) Uani d . 1 . .
    C C2 0.5440(6) 0.7571(4) -0.0503(4) 0.0469(11) Uani d . 1 . .
    C C3 0.6382(6) 0.6799(4) 0.0165(4) 0.0492(11) Uani d . 1 . .
    H H3 0.7412 0.6597 0.0031 0.059 Uiso calc R 1 . .
    C C4 0.5768(6) 0.6326(4) 0.1047(4) 0.0442(11) Uani d . 1 . .
    C C5 0.4217(6) 0.6592(4) 0.1229(4) 0.0447(11) Uani d . 1 . .
    C C6 0.3308(6) 0.7379(5) 0.0548(5) 0.0572(13) Uani d . 1 . .
    C C7 0.3908(7) 0.7872(4) -0.0317(4) 0.0560(13) Uani d . 1 . .
    H H7 0.3287 0.8403 -0.0772 0.067 Uiso calc R 1 . .
    C C8 0.1945(6) 0.4870(4) 0.2791(4) 0.0481(11) Uani d . 1 . .
    C C9 0.2910(6) 0.5720(4) 0.3715(4) 0.0499(11) Uani d . 1 . .
    C C10 0.3935(6) 0.6504(4) 0.3260(4) 0.0479(11) Uani d . 1 . .
    C C11 0.5976(6) 0.7869(4) 0.4693(4) 0.0536(12) Uani d . 1 . .
    H H11 0.5995 0.7314 0.5235 0.064 Uiso calc R 1 . .
    C C12 0.7032(6) 0.9052(4) 0.5094(4) 0.0486(11) Uani d . 1 . .
    C C13 0.8319(6) 0.9245(4) 0.6210(4) 0.0537(12) Uani d . 1 . .
    H H13 0.8455 0.8642 0.6705 0.064 Uiso calc R 1 . .
    C C14 0.9388(6) 1.0327(5) 0.6578(5) 0.0562(13) Uani d . 1 . .
    C C15 0.9172(7) 1.1235(5) 0.5880(6) 0.0684(15) Uani d . 1 . .
    H H15 0.9889 1.1970 0.6144 0.082 Uiso calc R 1 . .
    C C16 0.7875(8) 1.1046(5) 0.4773(6) 0.0702(15) Uani d . 1 . .
    H H16 0.7719 1.1660 0.4295 0.084 Uiso calc R 1 . .
    C C17 0.6811(7) 0.9957(5) 0.4373(5) 0.0576(13) Uani d . 1 . .
    H H17 0.5953 0.9833 0.3624 0.069 Uiso calc R 1 . .
    C C18 0.0592(7) 0.3896(5) 0.2816(5) 0.0575(13) Uani 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
    Br1 C14 . 1.890(5) ?
    Cl1 C6 . 1.723(5) ?
    Cl2 C4 . 1.728(4) ?
    Cl3 C9 . 1.709(5) ?
    F1 C1 . 1.275(7) ?
    F2 C1 . 1.268(7) ?
    F3 C1 . 1.264(7) ?
    N1 N2 . 1.347(5) ?
    N1 C10 . 1.366(6) ?
    N1 C5 . 1.423(5) ?
    N2 C8 . 1.336(6) ?
    N3 C18 . 1.132(6) ?
    N4 C10 . 1.386(6) ?
    N4 C11 . 1.271(6) ?
    C1 C2 . 1.486(7) ?
    C2 C3 . 1.370(6) ?
    C2 C7 . 1.377(6) ?
    C3 C4 . 1.387(6) ?
    C3 H3 . 0.930 ?
    C4 C5 . 1.374(6) ?
    C5 C6 . 1.379(7) ?
    C6 C7 . 1.372(7) ?
    C7 H7 . 0.930 ?
    C8 C9 . 1.385(6) ?
    C8 C18 . 1.442(7) ?
    C9 C10 . 1.367(6) ?
    C11 C12 . 1.467(7) ?
    C11 H11 . 0.930 ?
    C12 C17 . 1.380(7) ?
    C12 C13 . 1.389(7) ?
    C13 C14 . 1.371(7) ?
    C13 H13 . 0.930 ?
    C14 C15 . 1.368(8) ?
    C15 C16 . 1.384(8) ?
    C15 H15 . 0.930 ?
    C16 C17 . 1.379(7) ?
    C16 H16 . 0.930 ?
    C17 H17 . 0.930 ?
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
    N2 N1 C10 . . 113.6(4) ?
    N2 N1 C5 . . 119.3(4) ?
    C10 N1 C5 . . 127.1(4) ?
    C8 N2 N1 . . 103.2(4) ?
    C11 N4 C10 . . 120.3(4) ?
    F3 C1 F2 . . 103.5(6) ?
    F3 C1 F1 . . 104.4(6) ?
    F2 C1 F1 . . 104.7(6) ?
    F3 C1 C2 . . 113.9(5) ?
    F2 C1 C2 . . 114.9(5) ?
    F1 C1 C2 . . 114.2(5) ?
    C3 C2 C7 . . 121.3(4) ?
    C3 C2 C1 . . 119.4(5) ?
    C7 C2 C1 . . 119.3(5) ?
    C2 C3 C4 . . 118.6(4) ?
    C2 C3 H3 . . 120.7 ?
    C4 C3 H3 . . 120.7 ?
    C5 C4 C3 . . 121.1(4) ?
    C5 C4 Cl2 . . 119.7(3) ?
    C3 C4 Cl2 . . 119.1(3) ?
    C4 C5 C6 . . 118.8(4) ?
    C4 C5 N1 . . 121.4(4) ?
    C6 C5 N1 . . 119.8(4) ?
    C7 C6 C5 . . 121.0(4) ?
    C7 C6 Cl1 . . 119.4(4) ?
    C5 C6 Cl1 . . 119.6(4) ?
    C6 C7 C2 . . 119.2(4) ?
    C6 C7 H7 . . 120.4 ?
    C2 C7 H7 . . 120.4 ?
    N2 C8 C9 . . 112.2(4) ?
    N2 C8 C18 . . 120.9(4) ?
    C9 C8 C18 . . 126.9(4) ?
    C10 C9 C8 . . 106.1(4) ?
    C10 C9 Cl3 . . 128.0(4) ?
    C8 C9 Cl3 . . 125.9(4) ?
    N1 C10 C9 . . 104.9(4) ?
    N1 C10 N4 . . 116.8(4) ?
    C9 C10 N4 . . 137.9(4) ?
    N4 C11 C12 . . 120.7(4) ?
    N4 C11 H11 . . 119.7 ?
    C12 C11 H11 . . 119.7 ?
    C17 C12 C13 . . 119.9(5) ?
    C17 C12 C11 . . 121.4(5) ?
    C13 C12 C11 . . 118.6(4) ?
    C14 C13 C12 . . 119.6(5) ?
    C14 C13 H13 . . 120.2 ?
    C12 C13 H13 . . 120.2 ?
    C15 C14 C13 . . 121.1(5) ?
    C15 C14 Br1 . . 119.3(4) ?
    C13 C14 Br1 . . 119.6(4) ?
    C14 C15 C16 . . 119.2(5) ?
    C14 C15 H15 . . 120.4 ?
    C16 C15 H15 . . 120.4 ?
    C17 C16 C15 . . 120.7(5) ?
    C17 C16 H16 . . 119.6 ?
    C15 C16 H16 . . 119.6 ?
    C16 C17 C12 . . 119.4(5) ?
    C16 C17 H17 . . 120.3 ?
    C12 C17 H17 . . 120.3 ?
    N3 C18 C8 . . 177.3(6) ?
