##############################################################################
###                                                                        ###
###        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_3
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2-(2-Bromo-5-methoxyphenyl)-6-phenyl-1,3-thiazolo[3,2-b][1,2,4]triazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H12 Br N3 O S'
_chemical_formula_sum     'C17 H12 Br N3 O S'
_chemical_formula_iupac     'C17 H12 Br N3 O S'
_chemical_formula_weight     386.27
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_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'
    '-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     14.9271(13)
_cell_length_b     10.9247(13)
_cell_length_c     18.8582(16)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3075.3(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8171
_cell_measurement_theta_min     3.5
_cell_measurement_theta_max     25.9
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.669
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1552
_exptl_absorpt_coefficient_mu     2.816
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.4660
_exptl_absorpt_correction_T_max     0.8061
_exptl_special_details
;
Spectroscopic data: IR (KBr, ν, cm-1): 3118 and 3070 (--CH), 1475 (--C=
N--), 734 (C---Br); ¹H NMR (300 MHz, DMSO-d₆, δ, p.p.m.): 3.8 (s, 3H,
--OCH₃), 7.03 (dd, J = 8.7 Hz, 1H, ArH), 7.44 (s, 1H, ArH), 7.55 (m, 3H,
ArH), 7.67 (d, J = 8.7 Hz, 1H, ArH), 8.01 (s, 1H, ArH), 8.27 (d, J = 7.8 Hz,
1H, NH); ¹³C NMR (75 MHz, DMSO-d₆, δ, p.p.m.): 55.62, 111.14, 111.47,
116.96, 117.31, 126.27, 127.57, 129.00, 129.69, 131.52, 132.57, 134.66,
158.43; DEPT: 55.64, 111.16, 116.98, 117.34, 126.29, 129.04, 129.73, 134.68;
FAB-MS: m/z 386 (I = 100%, M+), 387 (I = 20%, M+1), 388 (I
= 95%, M+2).
;
_diffrn_ambient_temperature     173(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     'Stoe IPDS II two-circle'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10330
_diffrn_reflns_av_R_equivalents     0.0638
_diffrn_reflns_av_sigmaI/netI     0.0481
_diffrn_reflns_theta_min     3.48
_diffrn_reflns_theta_max     25.61
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     19
_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     2883
_reflns_number_gt     2189
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0558
_refine_ls_R_factor_gt     0.0370
_refine_ls_wR_factor_gt     0.0812
_refine_ls_wR_factor_ref     0.0871
_refine_ls_goodness_of_fit_ref     0.981
_refine_ls_restrained_S_all     0.981
_refine_ls_number_reflns     2883
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0505P)²] 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     0.547
_refine_diff_density_min     -0.801
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.0046(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2001)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-AREA'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_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 0.51020(2) 0.22648(3) 0.601791(16) 0.02619(14) Uani d . 1 . .
    S S1 0.24276(6) 0.65017(9) 0.44150(4) 0.0305(2) Uani d . 1 . .
    C C2 0.2341(2) 0.6757(3) 0.53258(17) 0.0252(7) Uani d . 1 . .
    H H2 0.1955 0.7360 0.5522 0.030 Uiso calc R 1 . .
    C C3 0.28695(19) 0.6025(3) 0.57326(16) 0.0189(6) Uani d . 1 . .
    N N4 0.33621(16) 0.5240(2) 0.52838(13) 0.0167(5) Uani d . 1 . .
    C C5 0.3208(2) 0.5366(3) 0.45748(16) 0.0201(7) Uani d . 1 . .
    N N6 0.39689(16) 0.4322(2) 0.53952(13) 0.0176(5) Uani d . 1 . .
    C C7 0.41417(19) 0.3955(3) 0.47251(15) 0.0160(6) Uani d . 1 . .
    N N8 0.36851(17) 0.4577(3) 0.42021(14) 0.0220(6) Uani d . 1 . .
    C C11 0.2932(2) 0.6004(3) 0.65120(16) 0.0199(7) Uani d . 1 . .
    C C12 0.3503(2) 0.5207(3) 0.68784(16) 0.0238(7) Uani d . 1 . .
    H H12 0.3877 0.4658 0.6623 0.029 Uiso calc R 1 . .
    C C13 0.3523(2) 0.5218(3) 0.76212(18) 0.0281(8) Uani d . 1 . .
    H H13 0.3909 0.4672 0.7868 0.034 Uiso calc R 1 . .
    C C14 0.2984(2) 0.6020(4) 0.79987(17) 0.0289(8) Uani d . 1 . .
    H H14 0.3001 0.6024 0.8502 0.035 Uiso calc R 1 . .
    C C15 0.2420(2) 0.6815(4) 0.76413(18) 0.0310(8) Uani d . 1 . .
    H H15 0.2049 0.7362 0.7900 0.037 Uiso calc R 1 . .
    C C16 0.2397(2) 0.6812(3) 0.69055(18) 0.0268(7) Uani d . 1 . .
    H H16 0.2012 0.7366 0.6665 0.032 Uiso calc R 1 . .
    C C21 0.47465(19) 0.2939(3) 0.45363(16) 0.0181(6) Uani d . 1 . .
    C C22 0.51916(19) 0.2133(3) 0.50081(17) 0.0217(7) Uani d . 1 . .
    C C23 0.5720(2) 0.1191(3) 0.47531(18) 0.0267(8) Uani d . 1 . .
    H H23 0.6018 0.0669 0.5079 0.032 Uiso calc R 1 . .
    C C24 0.5824(2) 0.0991(3) 0.40270(18) 0.0257(7) Uani d . 1 . .
    H H24 0.6186 0.0336 0.3860 0.031 Uiso calc R 1 . .
    C C25 0.5392(2) 0.1763(3) 0.35519(16) 0.0216(7) Uani d . 1 . .
    C C26 0.4867(2) 0.2723(3) 0.38048(17) 0.0199(6) Uani d . 1 . .
    H H26 0.4580 0.3250 0.3474 0.024 Uiso calc R 1 . .
    O O27 0.54298(16) 0.1662(2) 0.28269(11) 0.0282(5) Uani d . 1 . .
    C C27 0.5943(2) 0.0665(4) 0.25456(19) 0.0332(8) Uani d . 1 . .
    H H27A 0.6569 0.0748 0.2695 0.050 Uiso calc R 1 . .
    H H27B 0.5910 0.0676 0.2027 0.050 Uiso calc R 1 . .
    H H27C 0.5701 -0.0111 0.2723 0.050 Uiso calc R 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 C22 . 1.915(3) ?
    S1 C5 . 1.728(3) ?
    S1 C2 . 1.745(3) ?
    C2 C3 . 1.361(5) ?
    C2 H2 . 0.9500 ?
    C3 N4 . 1.412(4) ?
    C3 C11 . 1.473(4) ?
    N4 C5 . 1.364(4) ?
    N4 N6 . 1.367(3) ?
    C5 N8 . 1.320(4) ?
    N6 C7 . 1.351(4) ?
    C7 N8 . 1.378(4) ?
    C7 C21 . 1.475(4) ?
    C11 C12 . 1.401(5) ?
    C11 C16 . 1.403(5) ?
    C12 C13 . 1.401(5) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.387(5) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.384(5) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.388(5) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C21 C26 . 1.411(4) ?
    C21 C22 . 1.417(4) ?
    C22 C23 . 1.383(5) ?
    C23 C24 . 1.395(5) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.389(5) ?
    C24 H24 . 0.9500 ?
    C25 O27 . 1.373(4) ?
    C25 C26 . 1.394(5) ?
    C26 H26 . 0.9500 ?
    O27 C27 . 1.434(4) ?
    C27 H27A . 0.9800 ?
    C27 H27B . 0.9800 ?
    C27 H27C . 0.9800 ?
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
    C5 S1 C2 . . 89.62(15) ?
    C3 C2 S1 . . 114.7(3) ?
    C3 C2 H2 . . 122.7 ?
    S1 C2 H2 . . 122.7 ?
    C2 C3 N4 . . 108.7(3) ?
    C2 C3 C11 . . 127.5(3) ?
    N4 C3 C11 . . 123.8(3) ?
    C5 N4 N6 . . 109.7(2) ?
    C5 N4 C3 . . 116.0(3) ?
    N6 N4 C3 . . 134.3(3) ?
    N8 C5 N4 . . 111.4(3) ?
    N8 C5 S1 . . 137.7(2) ?
    N4 C5 S1 . . 110.9(2) ?
    C7 N6 N4 . . 101.6(2) ?
    N6 C7 N8 . . 115.4(3) ?
    N6 C7 C21 . . 124.5(3) ?
    N8 C7 C21 . . 120.1(3) ?
    C5 N8 C7 . . 102.0(2) ?
    C12 C11 C16 . . 118.5(3) ?
    C12 C11 C3 . . 122.7(3) ?
    C16 C11 C3 . . 118.8(3) ?
    C11 C12 C13 . . 120.1(3) ?
    C11 C12 H12 . . 120.0 ?
    C13 C12 H12 . . 120.0 ?
    C14 C13 C12 . . 120.4(3) ?
    C14 C13 H13 . . 119.8 ?
    C12 C13 H13 . . 119.8 ?
    C15 C14 C13 . . 120.0(3) ?
    C15 C14 H14 . . 120.0 ?
    C13 C14 H14 . . 120.0 ?
    C14 C15 C16 . . 120.1(3) ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    C15 C16 C11 . . 121.0(3) ?
    C15 C16 H16 . . 119.5 ?
    C11 C16 H16 . . 119.5 ?
    C26 C21 C22 . . 116.8(3) ?
    C26 C21 C7 . . 116.1(3) ?
    C22 C21 C7 . . 127.1(3) ?
    C23 C22 C21 . . 120.8(3) ?
    C23 C22 Br1 . . 116.2(2) ?
    C21 C22 Br1 . . 123.0(2) ?
    C22 C23 C24 . . 121.4(3) ?
    C22 C23 H23 . . 119.3 ?
    C24 C23 H23 . . 119.3 ?
    C25 C24 C23 . . 119.1(3) ?
    C25 C24 H24 . . 120.5 ?
    C23 C24 H24 . . 120.5 ?
    O27 C25 C24 . . 125.1(3) ?
    O27 C25 C26 . . 115.1(3) ?
    C24 C25 C26 . . 119.8(3) ?
    C25 C26 C21 . . 122.1(3) ?
    C25 C26 H26 . . 119.0 ?
    C21 C26 H26 . . 119.0 ?
    C25 O27 C27 . . 116.8(3) ?
    O27 C27 H27A . . 109.5 ?
    O27 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    O27 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
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
    C5 S1 C2 C3 . . . . -0.2(3) ?
    S1 C2 C3 N4 . . . . 0.4(4) ?
    S1 C2 C3 C11 . . . . -178.7(3) ?
    C2 C3 N4 C5 . . . . -0.5(4) ?
    C11 C3 N4 C5 . . . . 178.6(3) ?
    C2 C3 N4 N6 . . . . -178.6(3) ?
    C11 C3 N4 N6 . . . . 0.6(5) ?
    N6 N4 C5 N8 . . . . -0.2(4) ?
    C3 N4 C5 N8 . . . . -178.7(3) ?
    N6 N4 C5 S1 . . . . 178.9(2) ?
    C3 N4 C5 S1 . . . . 0.4(3) ?
    C2 S1 C5 N8 . . . . 178.6(4) ?
    C2 S1 C5 N4 . . . . -0.1(3) ?
    C5 N4 N6 C7 . . . . 0.1(3) ?
    C3 N4 N6 C7 . . . . 178.3(3) ?
    N4 N6 C7 N8 . . . . -0.1(3) ?
    N4 N6 C7 C21 . . . . -178.1(3) ?
    N4 C5 N8 C7 . . . . 0.1(3) ?
    S1 C5 N8 C7 . . . . -178.6(3) ?
    N6 C7 N8 C5 . . . . 0.0(3) ?
    C21 C7 N8 C5 . . . . 178.1(3) ?
    C2 C3 C11 C12 . . . . -180.0(3) ?
    N4 C3 C11 C12 . . . . 1.0(5) ?
    C2 C3 C11 C16 . . . . 0.2(5) ?
    N4 C3 C11 C16 . . . . -178.8(3) ?
    C16 C11 C12 C13 . . . . 0.7(5) ?
    C3 C11 C12 C13 . . . . -179.1(3) ?
    C11 C12 C13 C14 . . . . -0.4(5) ?
    C12 C13 C14 C15 . . . . 0.1(5) ?
    C13 C14 C15 C16 . . . . -0.2(5) ?
    C14 C15 C16 C11 . . . . 0.6(5) ?
    C12 C11 C16 C15 . . . . -0.9(5) ?
    C3 C11 C16 C15 . . . . 178.9(3) ?
    N6 C7 C21 C26 . . . . -177.7(3) ?
    N8 C7 C21 C26 . . . . 4.4(4) ?
    N6 C7 C21 C22 . . . . 4.7(5) ?
    N8 C7 C21 C22 . . . . -173.2(3) ?
    C26 C21 C22 C23 . . . . 0.4(4) ?
    C7 C21 C22 C23 . . . . 177.9(3) ?
    C26 C21 C22 Br1 . . . . -179.4(2) ?
    C7 C21 C22 Br1 . . . . -1.8(4) ?
    C21 C22 C23 C24 . . . . -0.8(5) ?
    Br1 C22 C23 C24 . . . . 178.9(3) ?
    C22 C23 C24 C25 . . . . 0.5(5) ?
    C23 C24 C25 O27 . . . . -179.3(3) ?
    C23 C24 C25 C26 . . . . 0.3(5) ?
    O27 C25 C26 C21 . . . . 178.9(3) ?
    C24 C25 C26 C21 . . . . -0.7(5) ?
    C22 C21 C26 C25 . . . . 0.4(4) ?
    C7 C21 C26 C25 . . . . -177.5(3) ?
    C24 C25 O27 C27 . . . . 1.3(5) ?
    C26 C25 O27 C27 . . . . -178.3(3) ?
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
    C26 H26 N8 . 0.95 2.40 2.788(4) 103.9
    C12 H12 N6 . 0.95 2.35 3.040(4) 129.3
data_global
_journal_date_recd_electronic     2006-08-29
_journal_date_accepted     2006-09-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     o4444
_journal_page_last     o4445
_journal_paper_category     EO
_journal_coeditor_code     SG2057
_publ_contact_author_name     'Dr Michael Bolte'
_publ_contact_author_address
;
Institut fur Anorganische Chemie
J. W. Goethe-Universitat
Max-von-Laue-Strasse 7
60438 Frankfurt/Main
Germany
;
_publ_contact_author_email     bolte@chemie.uni-frankfurt.de
_publ_contact_author_fax     '49 69 798 29239'
_publ_contact_author_phone     '49 69 798 29136'
_publ_section_title
;
2-(2-Bromo-5-methoxyphenyl)-6-phenyl-1,3-thiazolo[3,2-b][1,2,4]triazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Yathirajan, H. S.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri
Mysore 570 006
India
;
    'Vijaya Raj, K. K.'
;
Department of Chemistry
Mangalore University
Mangalagangotri 574 199
India
;
    'Narayana, B.'
;
Department of Chemistry
Mangalore University
Mangalagangotri 574 199
India
;
    'Sarojini, B. K.'
;
Department of Chemistry
P. A. College of Engineering
Nadupadavu
Mangalore 574 153
India
;
    'Bolte, Michael'
;
Institut für Anorganische Chemie
J. W. Goethe-Universität Frankfurt
Max-von-Laue-Strasse 7
60438 Frankfurt/Main
Germany
;
