##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2005-12-07
_journal_date_accepted     2005-12-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      1
_journal_page_first     o334
_journal_page_last     o335
_journal_paper_category     EO
_journal_coeditor_code     DN6288
_publ_contact_author_name     ' Fang, Jian-Xin'
_publ_contact_author_address
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
_publ_contact_author_email     'shaoling1999@yahoo.com.cn'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
(E)-4-(4-Chlorophenyl)-N-(5-methyl-1,3-benzodioxol-5-ylmethylene)-
5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-amine
;
loop_
    _publ_author_name
    _publ_author_address
    'Shao, Ling'
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Zhang, Qing'
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Zhou, Xin'
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Fang, Jian-Xin'
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
data_I
_chemical_name_systematic
;
(E)-4-(4-Chlorophenyl)-N-(5-methyl-1,3-benzodioxol-5-ylmethylene)-
5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H12 Cl N5 O2 S'
_chemical_formula_sum     'C19 H12 Cl N5 O2 S'
_chemical_formula_iupac     'C19 H12 Cl N5 O2 S'
_chemical_formula_weight     409.85
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     -P1
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.8260(19)
_cell_length_b     8.929(2)
_cell_length_c     14.221(3)
_cell_angle_alpha     94.871(4)
_cell_angle_beta     92.332(4)
_cell_angle_gamma     114.170(4)
_cell_volume     900.2(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1873
_cell_measurement_theta_min     2.86
_cell_measurement_theta_max     26.28
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.512
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     420
_exptl_absorpt_coefficient_mu     0.355
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.910
_exptl_absorpt_correction_T_max     0.945
_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     4582
_diffrn_reflns_av_R_equivalents     0.0286
_diffrn_reflns_av_sigmaI/netI     0.0466
_diffrn_reflns_theta_min     1.44
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_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     3160
_reflns_number_gt     2302
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0684
_refine_ls_R_factor_gt     0.0450
_refine_ls_wR_factor_gt     0.1110
_refine_ls_wR_factor_ref     0.1265
_refine_ls_goodness_of_fit_ref     1.014
_refine_ls_restrained_S_all     1.014
_refine_ls_number_reflns     3160
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0622P)²+0.3304P] 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     0.317
_refine_diff_density_min     -0.410
_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'
    'S' 'S' 0.1246 0.1234
                         '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, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                                'SHELXTL (Bruker, 1999) and PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL'
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
    S1 1.26020(9) 0.46507(8) 0.50351(5) 0.0461(2) Uani d . 1 . . S
    Cl1 0.66432(13) 0.29773(17) -0.03482(6) 0.1048(4) Uani d . 1 . . Cl
    O1 0.6359(3) -0.2717(2) 0.87759(13) 0.0562(5) Uani d . 1 . . O
    O2 0.9087(3) -0.0324(2) 0.90043(13) 0.0552(5) Uani d . 1 . . O
    N1 1.3546(3) 0.6178(2) 0.34565(15) 0.0415(5) Uani d . 1 . . N
    N2 1.4619(3) 0.7640(3) 0.39798(16) 0.0554(6) Uani d . 1 . . N
    N3 1.5589(4) 0.7588(3) 0.25117(18) 0.0631(7) Uani d . 1 . . N
    N4 0.9525(3) 0.2587(2) 0.41150(14) 0.0405(5) Uani d . 1 . . N
    N5 1.0020(3) 0.2142(3) 0.57465(14) 0.0449(5) Uani d . 1 . . N
    C1 1.0451(3) 0.3735(3) 0.35029(17) 0.0371(6) Uani d . 1 . . C
    C2 0.9531(3) 0.3571(3) 0.25549(18) 0.0400(6) Uani d . 1 . . C
    C3 0.8440(4) 0.2022(3) 0.20817(19) 0.0467(7) Uani d . 1 . . C
    H3 0.8310 0.1086 0.2367 0.056 Uiso calc R 1 . . H
    C4 0.7545(4) 0.1842(4) 0.1200(2) 0.0577(8) Uani d . 1 . . C
    H4 0.6815 0.0794 0.0893 0.069 Uiso calc R 1 . . H
    C5 0.7739(4) 0.3220(5) 0.0777(2) 0.0638(9) Uani d . 1 . . C
    C6 0.8768(5) 0.4763(5) 0.1230(2) 0.0747(10) Uani d . 1 . . C
    H6 0.8870 0.5689 0.0941 0.090 Uiso calc R 1 . . H
    C7 0.9662(4) 0.4948(4) 0.2119(2) 0.0608(8) Uani d . 1 . . C
    H7 1.0356 0.6001 0.2428 0.073 Uiso calc R 1 . . H
    C8 1.2142(3) 0.4906(3) 0.38863(17) 0.0397(6) Uani d . 1 . . C
    C9 1.4181(4) 0.6178(3) 0.2594(2) 0.0566(8) Uani d . 1 . . C
    H9 1.3688 0.5296 0.2119 0.068 Uiso calc R 1 . . H
    C10 1.5792(4) 0.8412(4) 0.3368(2) 0.0654(9) Uani d . 1 . . C
    H10 1.6716 0.9478 0.3522 0.078 Uiso calc R 1 . . H
    C11 1.0482(3) 0.2945(3) 0.49322(17) 0.0391(6) Uani d . 1 . . C
    C12 0.8471(4) 0.0866(3) 0.57139(18) 0.0446(6) Uani d . 1 . . C
    H12 0.7695 0.0518 0.5153 0.054 Uiso calc R 1 . . H
    C13 0.7873(4) -0.0064(3) 0.65205(17) 0.0410(6) Uani d . 1 . . C
    C14 0.8979(4) 0.0432(3) 0.73899(18) 0.0415(6) Uani d . 1 . . C
    H14 1.0110 0.1368 0.7476 0.050 Uiso calc R 1 . . H
    C15 0.8307(4) -0.0528(3) 0.80944(17) 0.0408(6) Uani d . 1 . . C
    C16 0.6653(4) -0.1945(3) 0.79674(17) 0.0417(6) Uani d . 1 . . C
    C17 0.5543(4) -0.2444(3) 0.71386(19) 0.0486(7) Uani d . 1 . . C
    H17 0.4418 -0.3387 0.7064 0.058 Uiso calc R 1 . . H
    C18 0.6187(4) -0.1462(3) 0.64105(18) 0.0476(7) Uani d . 1 . . C
    H18 0.5469 -0.1751 0.5833 0.057 Uiso calc R 1 . . H
    C19 0.7965(4) -0.1776(4) 0.9421(2) 0.0573(8) Uani d . 1 . . C
    H19A 0.8682 -0.2419 0.9535 0.069 Uiso calc R 1 . . H
    H19B 0.7577 -0.1477 1.0021 0.069 Uiso calc R 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
    S1 C8 . 1.713(3) ?
    S1 C11 . 1.722(3) ?
    Cl1 C5 . 1.738(3) ?
    O1 C16 . 1.370(3) ?
    O1 C19 . 1.427(3) ?
    O2 C15 . 1.373(3) ?
    O2 C19 . 1.429(3) ?
    N1 C9 . 1.342(3) ?
    N1 N2 . 1.360(3) ?
    N1 C8 . 1.421(3) ?
    N2 C10 . 1.312(4) ?
    N3 C9 . 1.309(3) ?
    N3 C10 . 1.336(4) ?
    N4 C11 . 1.298(3) ?
    N4 C1 . 1.389(3) ?
    N5 C12 . 1.275(3) ?
    N5 C11 . 1.396(3) ?
    C1 C8 . 1.362(3) ?
    C1 C2 . 1.469(3) ?
    C2 C3 . 1.387(4) ?
    C2 C7 . 1.393(4) ?
    C3 C4 . 1.375(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.371(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.364(5) ?
    C6 C7 . 1.383(4) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C12 C13 . 1.453(4) ?
    C12 H12 . 0.9300 ?
    C13 C18 . 1.387(4) ?
    C13 C14 . 1.407(3) ?
    C14 C15 . 1.354(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.382(4) ?
    C16 C17 . 1.361(4) ?
    C17 C18 . 1.389(4) ?
    C17 H17 . 0.9300 ?
    C18 H18 . 0.9300 ?
    C19 H19A . 0.9700 ?
    C19 H19B . 0.9700 ?
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
    C8 S1 C11 . . 88.10(12) ?
    C16 O1 C19 . . 106.1(2) ?
    C15 O2 C19 . . 106.3(2) ?
    C9 N1 N2 . . 109.1(2) ?
    C9 N1 C8 . . 131.0(2) ?
    N2 N1 C8 . . 119.6(2) ?
    C10 N2 N1 . . 101.3(2) ?
    C9 N3 C10 . . 102.1(2) ?
    C11 N4 C1 . . 110.7(2) ?
    C12 N5 C11 . . 118.3(2) ?
    C8 C1 N4 . . 113.4(2) ?
    C8 C1 C2 . . 128.3(2) ?
    N4 C1 C2 . . 118.3(2) ?
    C3 C2 C7 . . 117.9(3) ?
    C3 C2 C1 . . 120.5(2) ?
    C7 C2 C1 . . 121.6(2) ?
    C4 C3 C2 . . 121.4(3) ?
    C4 C3 H3 . . 119.3 ?
    C2 C3 H3 . . 119.3 ?
    C5 C4 C3 . . 119.5(3) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    C6 C5 C4 . . 120.8(3) ?
    C6 C5 Cl1 . . 120.2(3) ?
    C4 C5 Cl1 . . 119.0(3) ?
    C5 C6 C7 . . 119.9(3) ?
    C5 C6 H6 . . 120.1 ?
    C7 C6 H6 . . 120.1 ?
    C6 C7 C2 . . 120.6(3) ?
    C6 C7 H7 . . 119.7 ?
    C2 C7 H7 . . 119.7 ?
    C1 C8 N1 . . 129.6(2) ?
    C1 C8 S1 . . 111.83(19) ?
    N1 C8 S1 . . 118.47(18) ?
    N3 C9 N1 . . 110.8(2) ?
    N3 C9 H9 . . 124.6 ?
    N1 C9 H9 . . 124.6 ?
    N2 C10 N3 . . 116.6(3) ?
    N2 C10 H10 . . 121.7 ?
    N3 C10 H10 . . 121.7 ?
    N4 C11 N5 . . 128.8(2) ?
    N4 C11 S1 . . 115.96(19) ?
    N5 C11 S1 . . 115.28(18) ?
    N5 C12 C13 . . 122.4(2) ?
    N5 C12 H12 . . 118.8 ?
    C13 C12 H12 . . 118.8 ?
    C18 C13 C14 . . 120.7(2) ?
    C18 C13 C12 . . 118.3(2) ?
    C14 C13 C12 . . 120.9(2) ?
    C15 C14 C13 . . 116.4(2) ?
    C15 C14 H14 . . 121.8 ?
    C13 C14 H14 . . 121.8 ?
    C14 C15 O2 . . 128.4(2) ?
    C14 C15 C16 . . 122.3(2) ?
    O2 C15 C16 . . 109.3(2) ?
    C17 C16 O1 . . 127.4(2) ?
    C17 C16 C15 . . 122.6(2) ?
    O1 C16 C15 . . 110.1(2) ?
    C16 C17 C18 . . 116.1(2) ?
    C16 C17 H17 . . 122.0 ?
    C18 C17 H17 . . 122.0 ?
    C13 C18 C17 . . 121.9(2) ?
    C13 C18 H18 . . 119.1 ?
    C17 C18 H18 . . 119.1 ?
    O1 C19 O2 . . 107.6(2) ?
    O1 C19 H19A . . 110.2 ?
    O2 C19 H19A . . 110.2 ?
    O1 C19 H19B . . 110.2 ?
    O2 C19 H19B . . 110.2 ?
    H19A C19 H19B . . 108.5 ?
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
    C9 H9 O1 2_756 0.93 2.52 3.371(4) 152.2
