##############################################################################
###                                                                        ###
###        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.                                        #
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# 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     2006-08-10
_journal_date_accepted     2006-09-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     o4499
_journal_page_last     o4500
_journal_paper_category     EO
_journal_coeditor_code     HB2117
_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
;
4-Bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-furyl)methyleneamino]-
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
;
    'Li, Jin-Hai' .
;
Department of Chemistry
Wenzhou University
325027 Wenzhou
People's Republic of China
;
data_I
_chemical_name_systematic
;
4-Bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-furyl)methyleneamino]-
1H-pyrazole-3-carbonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H6 Br Cl2 F3 N4 O'
_chemical_formula_sum     'C16 H6 Br Cl2 F3 N4 O'
_chemical_formula_iupac     'C16 H6 Br Cl2 F3 N4 O'
_chemical_formula_weight     478.06
_chemical_melting_point     '432-433'
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.561(2)
_cell_length_b     22.927(5)
_cell_length_c     8.4322(19)
_cell_angle_alpha     90.00
_cell_angle_beta     96.220(4)
_cell_angle_gamma     90.00
_cell_volume     1837.6(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3479
_cell_measurement_theta_min     2.34
_cell_measurement_theta_max     24.68
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.49
_exptl_crystal_size_mid     0.37
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.728
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     936
_exptl_absorpt_coefficient_mu     2.571
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.366
_exptl_absorpt_correction_T_max     0.627
_exptl_special_details
;IR (KBr, ν
cm⁻¹): 3444, 2242, 1607, 1385; ¹H NMR (C₃D₆O): δ 9.11 (s, 1H),
8.11 (s, 2H), 7.88 (dd, 1H), 7.39 (dd, 1H), 6.72
(dd, 1H); ¹³C NMR (C₃D₆O): δ 155.3, 154.7, 151.7, 149.9, 149.0,
137.7, 136.7 (2 C), 134.5, 130.0, 127.1 (2 C), 123.3, 114.2, 112.5, 112.4.
;
_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 CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9676
_diffrn_reflns_av_R_equivalents     0.0212
_diffrn_reflns_av_sigmaI/netI     0.0263
_diffrn_reflns_theta_min     2.14
_diffrn_reflns_theta_max     25.26
_diffrn_reflns_theta_full     25.26
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     9
_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     3302
_reflns_number_gt     2519
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0628
_refine_ls_R_factor_gt     0.0471
_refine_ls_wR_factor_gt     0.1249
_refine_ls_wR_factor_ref     0.1362
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     3302
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0669P)²+1.8001P] 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     0.644
_refine_diff_density_min     -0.669
_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'
    '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 0.22521(5) 0.72759(2) 0.92265(8) 0.0930(3) Uani d . 1 . .
    Cl Cl1 0.58296(14) 0.92319(6) 1.13007(13) 0.0774(4) Uani d . 1 . .
    Cl Cl2 0.45286(13) 0.89620(5) 0.49883(13) 0.0718(3) Uani d . 1 . .
    F F1 0.8423(4) 1.08118(16) 0.7604(5) 0.1312(14) Uani d . 1 . .
    F F2 0.8830(5) 1.0330(2) 0.5725(6) 0.1536(18) Uani d . 1 . .
    F F3 0.9813(4) 1.0133(3) 0.7968(10) 0.259(4) Uani d . 1 . .
    O O1 0.7600(3) 0.71005(12) 0.7911(3) 0.0630(7) Uani d . 1 . .
    N N1 0.4166(3) 0.87712(12) 0.8387(4) 0.0487(7) Uani d . 1 . .
    N N2 0.2870(3) 0.89978(13) 0.8499(4) 0.0558(8) Uani d . 1 . .
    N N3 -0.0535(4) 0.8609(2) 0.9115(5) 0.0847(12) Uani d . 1 . .
    N N4 0.5448(3) 0.78795(13) 0.8409(4) 0.0486(7) Uani d . 1 . .
    C C1 0.8680(6) 1.0261(2) 0.7261(8) 0.0876(15) Uani d . 1 . .
    C C2 0.7494(4) 0.98709(17) 0.7551(5) 0.0598(10) Uani d . 1 . .
    C C3 0.7247(4) 0.97558(17) 0.9099(5) 0.0609(11) Uani d . 1 . .
    H H3 0.7808 0.9922 0.9950 0.073 Uiso calc R 1 . .
    C C4 0.6155(4) 0.93901(16) 0.9364(5) 0.0529(9) Uani d . 1 . .
    C C5 0.5302(4) 0.91467(14) 0.8114(4) 0.0474(8) Uani d . 1 . .
    C C6 0.5577(4) 0.92709(15) 0.6569(5) 0.0524(9) Uani d . 1 . .
    C C7 0.6668(4) 0.96296(16) 0.6279(5) 0.0599(10) Uani d . 1 . .
    H H7 0.6847 0.9709 0.5239 0.072 Uiso calc R 1 . .
    C C8 0.4240(4) 0.81859(14) 0.8633(4) 0.0440(8) Uani d . 1 . .
    C C9 0.2904(4) 0.80250(15) 0.8911(5) 0.0506(9) Uani d . 1 . .
    C C10 0.2108(4) 0.85336(17) 0.8799(4) 0.0518(9) Uani d . 1 . .
    C C11 0.0634(4) 0.85882(18) 0.8968(5) 0.0610(10) Uani d . 1 . .
    C C12 0.5961(4) 0.75389(16) 0.9515(4) 0.0478(8) Uani d . 1 . .
    H H12 0.5558 0.7538 1.0471 0.057 Uiso calc R 1 . .
    C C13 0.7120(4) 0.71595(16) 0.9365(4) 0.0494(9) Uani d . 1 . .
    C C14 0.7864(4) 0.68091(18) 1.0433(5) 0.0615(10) Uani d . 1 . .
    H H14 0.7745 0.6770 1.1508 0.074 Uiso calc R 1 . .
    C C15 0.8852(4) 0.65151(19) 0.9608(6) 0.0696(12) Uani d . 1 . .
    H H15 0.9514 0.6244 1.0030 0.084 Uiso calc R 1 . .
    C C16 0.8654(5) 0.6700(2) 0.8112(6) 0.0735(12) Uani d . 1 . .
    H H16 0.9168 0.6572 0.7304 0.088 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
    Br1 0.0729(4) 0.0548(3) 0.1531(6) -0.0108(2) 0.0211(3) 0.0263(3)
    Cl1 0.0852(8) 0.0867(8) 0.0596(6) 0.0023(6) 0.0043(5) 0.0015(5)
    Cl2 0.0837(8) 0.0650(7) 0.0640(6) -0.0183(5) -0.0034(5) -0.0008(5)
    F1 0.143(3) 0.085(2) 0.172(4) -0.056(2) 0.041(3) -0.020(2)
    F2 0.139(3) 0.171(4) 0.164(4) -0.088(3) 0.074(3) -0.034(3)
    F3 0.059(2) 0.252(6) 0.447(10) -0.065(3) -0.060(4) 0.218(7)
    O1 0.0631(18) 0.0679(17) 0.0599(16) 0.0128(14) 0.0152(13) -0.0012(13)
    N1 0.0443(16) 0.0390(15) 0.0635(19) 0.0028(12) 0.0090(14) 0.0040(13)
    N2 0.0470(17) 0.0469(17) 0.073(2) 0.0065(14) 0.0051(15) 0.0002(15)
    N3 0.053(2) 0.102(3) 0.099(3) 0.009(2) 0.010(2) -0.009(2)
    N4 0.0486(17) 0.0436(16) 0.0545(17) 0.0053(13) 0.0106(14) 0.0048(14)
    C1 0.070(3) 0.081(4) 0.113(4) -0.027(3) 0.015(3) -0.008(3)
    C2 0.048(2) 0.048(2) 0.084(3) -0.0042(17) 0.011(2) -0.001(2)
    C3 0.047(2) 0.050(2) 0.083(3) 0.0025(17) -0.004(2) -0.012(2)
    C4 0.053(2) 0.048(2) 0.058(2) 0.0082(17) 0.0025(17) -0.0009(17)
    C5 0.0444(19) 0.0337(16) 0.064(2) 0.0041(14) 0.0069(17) 0.0023(15)
    C6 0.056(2) 0.0400(19) 0.060(2) -0.0008(16) 0.0040(18) -0.0007(16)
    C7 0.067(3) 0.047(2) 0.067(2) -0.0056(19) 0.014(2) 0.0046(18)
    C8 0.0471(19) 0.0403(18) 0.0446(18) 0.0026(14) 0.0047(15) 0.0025(14)
    C9 0.049(2) 0.0428(19) 0.061(2) -0.0018(16) 0.0082(17) 0.0056(16)
    C10 0.046(2) 0.052(2) 0.056(2) 0.0029(16) 0.0044(17) 0.0008(17)
    C11 0.051(2) 0.063(2) 0.069(3) 0.0022(19) 0.0039(19) -0.003(2)
    C12 0.047(2) 0.0442(18) 0.054(2) 0.0017(15) 0.0102(16) 0.0009(16)
    C13 0.050(2) 0.0440(19) 0.055(2) 0.0023(15) 0.0093(17) 0.0029(16)
    C14 0.057(2) 0.060(2) 0.067(2) 0.0128(19) 0.0092(19) 0.008(2)
    C15 0.052(2) 0.062(3) 0.094(3) 0.017(2) 0.005(2) 0.001(2)
    C16 0.059(3) 0.078(3) 0.086(3) 0.017(2) 0.023(2) -0.011(3)
_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
    C9 Br1 . 1.856(4) n
    Cl1 C4 . 1.734(4) ?
    Cl2 C6 . 1.730(4) ?
    C1 F1 . 1.324(6) ?
    C1 F2 . 1.328(7) ?
    C1 F3 . 1.215(7) n
    O1 C13 . 1.361(4) ?
    O1 C16 . 1.361(5) ?
    N1 N2 . 1.357(4) n
    N1 C5 . 1.424(4) n
    N1 C8 . 1.359(4) n
    N2 C10 . 1.329(5) n
    N3 C11 . 1.139(5) n
    N4 C8 . 1.383(4) n
    N4 C12 . 1.273(5) n
    C1 C2 . 1.485(6) ?
    C2 C7 . 1.377(6) ?
    C2 C3 . 1.377(6) ?
    C3 C4 . 1.376(6) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.379(5) ?
    C5 C6 . 1.386(5) ?
    C6 C7 . 1.370(5) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.373(5) n
    C9 C10 . 1.390(5) n
    C10 C11 . 1.437(5) n
    C12 C13 . 1.425(5) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.350(5) ?
    C14 C15 . 1.405(6) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.324(6) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 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
    C16 O1 C13 . . 105.8(3) ?
    N2 N1 C5 . . 119.9(3) n
    N2 N1 C8 . . 113.6(3) n
    C8 N1 C5 . . 126.4(3) n
    C10 N2 N1 . . 103.3(3) n
    C12 N4 C8 . . 118.2(3) n
    F3 C1 F1 . . 107.5(6) n
    F3 C1 F2 . . 108.8(6) ?
    F1 C1 F2 . . 98.1(5) ?
    F3 C1 C2 . . 115.5(5) ?
    F1 C1 C2 . . 112.0(5) ?
    F2 C1 C2 . . 113.4(5) ?
    C7 C2 C3 . . 121.2(4) ?
    C7 C2 C1 . . 119.9(4) ?
    C3 C2 C1 . . 118.9(4) ?
    C4 C3 C2 . . 118.8(4) ?
    C4 C3 H3 . . 120.6 ?
    C2 C3 H3 . . 120.6 ?
    C3 C4 C5 . . 121.3(4) ?
    C3 C4 Cl1 . . 119.8(3) ?
    C5 C4 Cl1 . . 118.9(3) ?
    C4 C5 C6 . . 118.6(3) ?
    C4 C5 N1 . . 121.3(3) ?
    C6 C5 N1 . . 120.1(3) ?
    C7 C6 C5 . . 121.1(4) ?
    C7 C6 Cl2 . . 119.8(3) ?
    C5 C6 Cl2 . . 119.1(3) ?
    C6 C7 C2 . . 119.1(4) ?
    C6 C7 H7 . . 120.5 ?
    C2 C7 H7 . . 120.5 ?
    N1 C8 C9 . . 104.9(3) n
    N1 C8 N4 . . 120.7(3) n
    C9 C8 N4 . . 133.9(3) n
    C8 C9 C10 . . 106.0(3) n
    C8 C9 Br1 . . 127.3(3) n
    C10 C9 Br1 . . 126.6(3) n
    N2 C10 C9 . . 112.1(3) n
    N2 C10 C11 . . 120.8(3) n
    C9 C10 C11 . . 127.0(4) n
    N3 C11 C10 . . 177.3(5) ?
    N4 C12 C13 . . 123.4(3) n
    N4 C12 H12 . . 118.3 ?
    C13 C12 H12 . . 118.3 ?
    C14 C13 O1 . . 109.7(3) ?
    C14 C13 C12 . . 131.5(4) ?
    O1 C13 C12 . . 118.8(3) ?
    C13 C14 C15 . . 106.8(4) ?
    C13 C14 H14 . . 126.6 ?
    C15 C14 H14 . . 126.6 ?
    C16 C15 C14 . . 106.5(4) ?
    C16 C15 H15 . . 126.7 ?
    C14 C15 H15 . . 126.7 ?
    C15 C16 O1 . . 111.2(4) ?
    C15 C16 H16 . . 124.4 ?
    O1 C16 H16 . . 124.4 ?
