##############################################################################
###                                                                        ###
###        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                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2005-11-01
_journal_date_accepted     2005-12-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      1
_journal_page_first     o91
_journal_page_last     o93
_journal_paper_category     EO
_journal_coeditor_code     OB6593
_publ_contact_author_name     'Fang, Jian-Xin'
_publ_contact_author_address
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
Peoples' Republic of China
;
_publ_contact_author_email     shaoling1999@yahoo.com.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
4-(4-Chlorophenyl)-N-phenyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-\
amine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Shao, Ling' .
;
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
;
4-(4-Chlorophenyl)-N-phenyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H12 Cl N5 S'
_chemical_formula_sum     'C17 H12 Cl N5 S'
_chemical_formula_iupac     'C17 H12 Cl N5 S'
_chemical_formula_weight     353.83
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     -P2yn
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     9.5139(18)
_cell_length_b     13.681(3)
_cell_length_c     12.439(3)
_cell_angle_alpha     90.00
_cell_angle_beta     98.828(3)
_cell_angle_gamma     90.00
_cell_volume     1599.9(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3277
_cell_measurement_theta_min     2.23
_cell_measurement_theta_max     26.39
_cell_measurement_temperature     294(2)
_exptl_crystal_description     parallelepiped
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.469
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     0.378
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9026
_exptl_absorpt_correction_T_max     0.9283
_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     8842
_diffrn_reflns_av_R_equivalents     0.0313
_diffrn_reflns_av_sigmaI/netI     0.0396
_diffrn_reflns_theta_min     2.23
_diffrn_reflns_theta_max     26.44
_diffrn_reflns_theta_full     26.44
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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     3279
_reflns_number_gt     2449
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0592
_refine_ls_R_factor_gt     0.0386
_refine_ls_wR_factor_gt     0.0920
_refine_ls_wR_factor_ref     0.1041
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     3279
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0499P)²+0.5099P] 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     0.232
_refine_diff_density_min     -0.332
_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'
    '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)'
_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 0.62799(5) 0.29951(4) 0.77969(5) 0.04107(16) Uani d . 1 . . S
    Cl1 0.37789(8) 0.87301(4) 0.94633(6) 0.0688(2) Uani d . 1 . . Cl
    N1 0.94670(18) 0.55483(14) 0.74501(17) 0.0498(5) Uani d . 1 . . N
    N2 0.86744(17) 0.48455(14) 0.88833(15) 0.0474(5) Uani d . 1 . . N
    N3 0.77183(15) 0.47228(12) 0.79540(13) 0.0340(4) Uani d . 1 . . N
    N4 0.41660(16) 0.39374(11) 0.83975(13) 0.0341(4) Uani d . 1 . . N
    N5 0.38380(17) 0.22234(13) 0.82124(15) 0.0400(4) Uani d . 1 . . N
    H5 0.427(3) 0.1713(19) 0.809(2) 0.054(7) Uiso d . 1 . . H
    C1 0.9687(2) 0.53416(17) 0.8525(2) 0.0497(6) Uani d . 1 . . C
    H1 1.0505 0.5538 0.8982 0.060 Uiso calc R 1 . . H
    C2 0.8222(2) 0.51438(17) 0.71211(18) 0.0455(5) Uani d . 1 . . C
    H2 0.7756 0.5150 0.6407 0.055 Uiso calc R 1 . . H
    C3 0.64023(19) 0.42529(14) 0.79944(16) 0.0340(4) Uani d . 1 . . C
    C4 0.52166(18) 0.46324(14) 0.83231(15) 0.0314(4) Uani d . 1 . . C
    C5 0.49206(18) 0.56457(14) 0.86172(15) 0.0321(4) Uani d . 1 . . C
    C6 0.5810(2) 0.64335(15) 0.8485(2) 0.0469(5) Uani d . 1 . . C
    H6 0.6656 0.6323 0.8215 0.056 Uiso calc R 1 . . H
    C7 0.5462(2) 0.73707(16) 0.8746(2) 0.0500(6) Uani d . 1 . . C
    H7 0.6065 0.7888 0.8650 0.060 Uiso calc R 1 . . H
    C8 0.4216(2) 0.75392(15) 0.91490(17) 0.0414(5) Uani d . 1 . . C
    C9 0.3323(2) 0.67798(16) 0.93032(18) 0.0433(5) Uani d . 1 . . C
    H9 0.2484 0.6897 0.9580 0.052 Uiso calc R 1 . . H
    C10 0.3683(2) 0.58415(15) 0.90442(17) 0.0382(5) Uani d . 1 . . C
    H10 0.3083 0.5327 0.9158 0.046 Uiso calc R 1 . . H
    C11 0.45743(18) 0.30659(14) 0.81708(16) 0.0341(4) Uani d . 1 . . C
    C12 0.25823(18) 0.20682(14) 0.86579(16) 0.0336(4) Uani d . 1 . . C
    C13 0.2227(2) 0.11027(15) 0.88219(18) 0.0418(5) Uani d . 1 . . C
    H13 0.2802 0.0602 0.8630 0.050 Uiso calc R 1 . . H
    C14 0.1027(2) 0.08796(17) 0.9267(2) 0.0524(6) Uani d . 1 . . C
    H14 0.0800 0.0230 0.9379 0.063 Uiso calc R 1 . . H
    C15 0.0162(2) 0.16115(18) 0.9548(2) 0.0563(6) Uani d . 1 . . C
    H15 -0.0646 0.1461 0.9852 0.068 Uiso calc R 1 . . H
    C16 0.0503(2) 0.25682(18) 0.9374(2) 0.0567(6) Uani d . 1 . . C
    H16 -0.0083 0.3064 0.9560 0.068 Uiso calc R 1 . . H
    C17 0.1707(2) 0.28099(15) 0.8926(2) 0.0474(6) Uani d . 1 . . C
    H17 0.1922 0.3460 0.8807 0.057 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 C3 . 1.740(2) yes
    S1 C11 . 1.7579(18) yes
    Cl1 C8 . 1.741(2) ?
    N1 C2 . 1.314(3) yes
    N1 C1 . 1.351(3) yes
    N2 C1 . 1.311(3) ?
    N2 N3 . 1.367(2) yes
    N3 C2 . 1.337(2) yes
    N3 C3 . 1.415(2) yes
    N4 C11 . 1.298(2) yes
    N4 C4 . 1.393(2) yes
    N5 C11 . 1.354(2) yes
    N5 C12 . 1.408(2) yes
    N5 H5 . 0.83(3) ?
    C1 H1 . 0.9300 ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.360(3) ?
    C4 C5 . 1.472(3) ?
    C5 C10 . 1.390(3) ?
    C5 C6 . 1.396(3) ?
    C6 C7 . 1.376(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.376(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.374(3) ?
    C9 C10 . 1.380(3) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C12 C17 . 1.385(3) ?
    C12 C13 . 1.386(3) ?
    C13 C14 . 1.378(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.375(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.374(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.388(3) ?
    C16 H16 . 0.9300 ?
    C17 H17 . 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
    C3 S1 C11 . . 87.29(9) yes
    C2 N1 C1 . . 102.45(17) yes
    C1 N2 N3 . . 101.80(17) yes
    C2 N3 N2 . . 109.34(16) yes
    C2 N3 C3 . . 130.37(18) yes
    N2 N3 C3 . . 120.21(15) ?
    C11 N4 C4 . . 111.76(15) yes
    C11 N5 C12 . . 128.22(17) yes
    C11 N5 H5 . . 115.7(17) ?
    C12 N5 H5 . . 114.5(17) ?
    N2 C1 N1 . . 115.7(2) yes
    N2 C1 H1 . . 122.1 ?
    N1 C1 H1 . . 122.1 ?
    N1 C2 N3 . . 110.7(2) yes
    N1 C2 H2 . . 124.7 ?
    N3 C2 H2 . . 124.7 ?
    C4 C3 N3 . . 128.04(18) no
    C4 C3 S1 . . 112.29(13) yes
    N3 C3 S1 . . 119.00(13) ?
    C3 C4 N4 . . 113.33(17) yes
    C3 C4 C5 . . 129.29(17) no
    N4 C4 C5 . . 117.37(15) ?
    C10 C5 C6 . . 117.45(18) ?
    C10 C5 C4 . . 118.81(16) no
    C6 C5 C4 . . 123.73(17) no
    C7 C6 C5 . . 121.27(19) ?
    C7 C6 H6 . . 119.4 ?
    C5 C6 H6 . . 119.4 ?
    C8 C7 C6 . . 119.7(2) ?
    C8 C7 H7 . . 120.2 ?
    C6 C7 H7 . . 120.2 ?
    C9 C8 C7 . . 120.66(19) ?
    C9 C8 Cl1 . . 120.17(16) ?
    C7 C8 Cl1 . . 119.18(16) ?
    C8 C9 C10 . . 119.35(18) ?
    C8 C9 H9 . . 120.3 ?
    C10 C9 H9 . . 120.3 ?
    C9 C10 C5 . . 121.59(19) ?
    C9 C10 H10 . . 119.2 ?
    C5 C10 H10 . . 119.2 ?
    N4 C11 N5 . . 126.85(17) ?
    N4 C11 S1 . . 115.28(14) ?
    N5 C11 S1 . . 117.86(14) no
    C17 C12 C13 . . 119.55(17) no
    C17 C12 N5 . . 124.18(18) ?
    C13 C12 N5 . . 116.27(17) no
    C14 C13 C12 . . 120.42(19) ?
    C14 C13 H13 . . 119.8 ?
    C12 C13 H13 . . 119.8 ?
    C15 C14 C13 . . 120.4(2) ?
    C15 C14 H14 . . 119.8 ?
    C13 C14 H14 . . 119.8 ?
    C16 C15 C14 . . 119.2(2) ?
    C16 C15 H15 . . 120.4 ?
    C14 C15 H15 . . 120.4 ?
    C15 C16 C17 . . 121.3(2) ?
    C15 C16 H16 . . 119.3 ?
    C17 C16 H16 . . 119.3 ?
    C12 C17 C16 . . 119.0(2) ?
    C12 C17 H17 . . 120.5 ?
    C16 C17 H17 . . 120.5 ?
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
    C1 N2 N3 C2 . . . . 0.2(2) ?
    C1 N2 N3 C3 . . . . -176.79(18) ?
    N3 N2 C1 N1 . . . . 0.0(3) ?
    C2 N1 C1 N2 . . . . -0.3(3) ?
    C1 N1 C2 N3 . . . . 0.4(2) ?
    N2 N3 C2 N1 . . . . -0.4(2) ?
    C3 N3 C2 N1 . . . . 176.20(19) ?
    C2 N3 C3 C4 . . . . -97.8(3) ?
    N2 N3 C3 C4 . . . . 78.5(3) yes
    C2 N3 C3 S1 . . . . 92.3(2) ?
    N2 N3 C3 S1 . . . . -91.4(2) ?
    C11 S1 C3 C4 . . . . 0.52(16) ?
    C11 S1 C3 N3 . . . . 171.89(16) ?
    N3 C3 C4 N4 . . . . -172.05(18) ?
    S1 C3 C4 N4 . . . . -1.7(2) ?
    N3 C3 C4 C5 . . . . 6.9(3) ?
    S1 C3 C4 C5 . . . . 177.28(16) ?
    C11 N4 C4 C3 . . . . 2.3(2) ?
    C11 N4 C4 C5 . . . . -176.81(17) no
    C3 C4 C5 C10 . . . . -173.1(2) yes
    N4 C4 C5 C10 . . . . 5.8(3) ?
    C3 C4 C5 C6 . . . . 7.4(3) ?
    N4 C4 C5 C6 . . . . -173.69(19) ?
    C10 C5 C6 C7 . . . . -1.3(3) ?
    C4 C5 C6 C7 . . . . 178.2(2) ?
    C5 C6 C7 C8 . . . . 0.2(4) ?
    C6 C7 C8 C9 . . . . 0.6(4) ?
    C6 C7 C8 Cl1 . . . . -179.37(19) ?
    C7 C8 C9 C10 . . . . -0.3(3) ?
    Cl1 C8 C9 C10 . . . . 179.66(16) ?
    C8 C9 C10 C5 . . . . -0.8(3) ?
    C6 C5 C10 C9 . . . . 1.6(3) ?
    C4 C5 C10 C9 . . . . -177.90(19) ?
    C4 N4 C11 N5 . . . . 176.91(19) ?
    C4 N4 C11 S1 . . . . -1.9(2) ?
    C12 N5 C11 N4 . . . . -10.5(4) yes
    C12 N5 C11 S1 . . . . 168.27(17) ?
    C3 S1 C11 N4 . . . . 0.80(16) ?
    C3 S1 C11 N5 . . . . -178.09(17) no
    C11 N5 C12 C17 . . . . 14.8(3) yes
    C11 N5 C12 C13 . . . . -165.6(2) ?
    C17 C12 C13 C14 . . . . -1.2(3) ?
    N5 C12 C13 C14 . . . . 179.2(2) ?
    C12 C13 C14 C15 . . . . 0.4(4) ?
    C13 C14 C15 C16 . . . . 0.3(4) ?
    C14 C15 C16 C17 . . . . -0.3(4) ?
    C13 C12 C17 C16 . . . . 1.3(3) ?
    N5 C12 C17 C16 . . . . -179.2(2) ?
    C15 C16 C17 C12 . . . . -0.5(4) ?
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
    N5 H5 N1 2_646 0.83(3) 2.17(3) 2.990(2) 170(2)
    C13 H13 Cl1 1_545 0.93 2.87 3.605(2) 137
