#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013903.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2013903
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o356
_journal_page_last  o357
_publ_section_title
;
6-(2-Fluorobenzylidene)-2-[1-(2-fluoro-4-biphenyl)ethyl]thiazolo[3,2-b]
-1,2,4-triazol-5(6H)-one
;
loop_
_publ_author_name
  "K\"oysal, Yavuz"
  "I\,s\?ik, \,Samil"
  "Do\~gda\,s, Emine"
  'Tozkoparan, Birsen'
  "Ertan, Mevl\"ut"
_chemical_formula_moiety  'C25 H17 F2 N3 O S'
_chemical_formula_sum  'C25 H17 F2 N3 O S'
_chemical_formula_iupac  'C25 H17 F2 N3 O S'
_chemical_formula_weight  445.48
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'F d d 2'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z'
  '-x+1/4, y+1/4, z+1/4'
  'x+3/4, -y+3/4, z+1/4'
  'x, y+1/2, z+1/2'
  '-x, -y+1/2, z+1/2'
  '-x+1/4, y+3/4, z+3/4'
  'x+3/4, -y+5/4, z+3/4'
  'x+1/2, y, z+1/2'
  '-x+1/2, -y, z+1/2'
  '-x+3/4, y+1/4, z+3/4'
  'x+5/4, -y+3/4, z+3/4'
  'x+1/2, y+1/2, z'
  '-x+1/2, -y+1/2, z'
  '-x+3/4, y+3/4, z+1/4'
  'x+5/4, -y+5/4, z+1/4'
_cell_length_a  24.059(3)
_cell_length_b  54.213(5)
_cell_length_c  6.5223(5)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  8507.3(15)
_cell_formula_units_Z  16
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.391
_diffrn_ambient_temperature  293(2)
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 0.07714(6) 0.17418(3) 0.6643(7) 0.0940(5) Uani d . 1 . . S
  N1 0.01094(17) 0.17434(8) 0.3538(7) 0.0721(13) Uani d . 1 . . N
  C16 -0.1676(2) 0.24505(9) 0.6269(9) 0.0774(16) Uani d . 1 . . C
  H16 -0.1969 0.2366 0.6883 0.093 Uiso calc R 1 . . H
  C14 -0.0880(2) 0.24472(10) 0.3935(9) 0.0689(15) Uani d . 1 . . C
  C11 -0.0236(2) 0.20917(11) 0.3207(10) 0.0742(17) Uani d . 1 . . C
  F1 -0.10176(11) 0.30505(6) 0.6125(6) 0.1113(12) Uani d . 1 . . F
  C17 -0.1577(2) 0.26982(11) 0.6725(9) 0.0671(15) Uani d . 1 . . C
  C19 -0.0778(2) 0.26911(9) 0.4342(9) 0.0721(15) Uani d . 1 . . C
  H19 -0.0484 0.2775 0.3737 0.087 Uiso calc R 1 . . H
  N2 0.00902(17) 0.21042(9) 0.4935(8) 0.0838(15) Uani d . 1 . . N
  N3 -0.02406(16) 0.18772(9) 0.2268(8) 0.0792(13) Uani d . 1 . . N
  C10 0.0291(2) 0.18827(11) 0.5010(10) 0.0764(17) Uani d . 1 . . C
  C18 -0.1137(2) 0.28048(9) 0.5698(9) 0.0708(16) Uani d . 1 . . C
  C20 -0.1909(2) 0.28429(10) 0.8210(9) 0.0682(15) Uani d . 1 . . C
  C12 -0.0502(2) 0.23210(10) 0.2327(9) 0.0784(17) Uani d . 1 . . C
  H12 -0.0202 0.2437 0.1999 0.094 Uiso calc R 1 . . H
  O1 0.02261(17) 0.13589(7) 0.2060(8) 0.1104(16) Uani d . 1 . . O
  C2 0.1233(2) 0.09494(13) 0.8111(12) 0.104(2) Uani d . 1 . . C
  C25 -0.2119(2) 0.30721(11) 0.7762(11) 0.103(2) Uani d . 1 . . C
  H25 -0.2047 0.3143 0.6492 0.123 Uiso calc R 1 . . H
  C15 -0.1324(2) 0.23315(9) 0.4856(10) 0.0776(18) Uani d . 1 . . C
  H15 -0.1395 0.2167 0.4531 0.093 Uiso calc R 1 . . H
  C8 0.0705(2) 0.14711(9) 0.5165(9) 0.0748(17) Uani d . 1 . . C
  C6 0.1627(3) 0.13439(12) 0.8337(12) 0.110(3) Uani d . 1 . . C
  H6 0.1673 0.1505 0.7885 0.133 Uiso calc R 1 . . H
  C3 0.1514(3) 0.08637(12) 0.9763(12) 0.115(3) Uani d . 1 . . C
  H3 0.1473 0.0702 1.0215 0.138 Uiso calc R 1 . . H
  C1 0.1268(2) 0.11855(10) 0.7323(10) 0.0758(17) Uani d . 1 . . C
  C9 0.0327(2) 0.15059(11) 0.3371(10) 0.085(2) Uani d . 1 . . C
  C13 -0.0803(2) 0.22664(11) 0.0374(9) 0.093(2) Uani d . 1 . . C
  H13C -0.1107 0.2156 0.0647 0.111 Uiso calc R 1 . . H
  H13B -0.0553 0.2191 -0.0584 0.111 Uiso calc R 1 . . H
  H13A -0.0945 0.2417 -0.0196 0.111 Uiso calc R 1 . . H
  C22 -0.2337(2) 0.28721(14) 1.1543(12) 0.108(2) Uani d . 1 . . C
  H22 -0.2412 0.2805 1.2827 0.130 Uiso calc R 1 . . H
  C21 -0.2016(2) 0.27401(11) 1.0111(10) 0.0835(19) Uani d . 1 . . C
  H21 -0.1877 0.2585 1.0439 0.100 Uiso calc R 1 . . H
  C4 0.1854(3) 0.10215(15) 1.0715(11) 0.111(2) Uani d . 1 . . C
  H4 0.2053 0.0969 1.1859 0.133 Uiso calc R 1 . . H
  C23 -0.2537(3) 0.30999(13) 1.1019(15) 0.119(3) Uani d . 1 . . C
  H23 -0.2748 0.3188 1.1962 0.143 Uiso calc R 1 . . H
  C5 0.1916(3) 0.12579(13) 1.0041(13) 0.120(3) Uani d . 1 . . C
  H5 0.2156 0.1364 1.0733 0.144 Uiso calc R 1 . . H
  C7 0.0932(2) 0.12531(9) 0.5593(9) 0.0808(18) Uani d . 1 . . C
  H7 0.0864 0.1128 0.4647 0.097 Uiso calc R 1 . . H
  C24 -0.2435(3) 0.31973(12) 0.9183(14) 0.115(2) Uani d . 1 . . C
  H24 -0.2578 0.3352 0.8856 0.138 Uiso calc R 1 . . H
  F2 0.08862(16) 0.07911(6) 0.7174(7) 0.164(2) Uani d . 1 . . F
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
  S1 0.1255(12) 0.0651(9) 0.0913(13) 0.0232(9) -0.0458(10) -0.0145(11)
  N1 0.092(3) 0.048(3) 0.077(4) 0.017(2) -0.030(3) -0.009(3)
  C16 0.110(4) 0.052(4) 0.071(4) 0.026(3) -0.020(4) -0.007(4)
  C14 0.089(4) 0.059(4) 0.058(4) 0.021(3) -0.019(3) -0.003(4)
  C11 0.086(4) 0.061(4) 0.076(5) 0.024(3) -0.020(4) -0.010(4)
  F1 0.135(3) 0.080(2) 0.120(3) -0.0026(17) 0.031(2) -0.006(2)
  C17 0.061(3) 0.074(4) 0.067(4) 0.009(3) 0.004(3) 0.008(4)
  C19 0.089(4) 0.060(4) 0.067(5) 0.017(3) -0.002(3) 0.005(4)
  N2 0.106(4) 0.071(4) 0.074(4) 0.033(3) -0.027(3) -0.024(3)
  N3 0.100(3) 0.064(3) 0.074(4) 0.018(3) -0.018(3) 0.011(3)
  C10 0.089(4) 0.060(4) 0.081(5) 0.021(3) -0.028(4) 0.005(4)
  C18 0.100(4) 0.038(3) 0.073(5) 0.012(3) -0.010(4) -0.002(3)
  C20 0.082(4) 0.061(4) 0.062(5) 0.007(3) 0.010(3) -0.004(4)
  C12 0.094(4) 0.059(4) 0.082(5) 0.022(3) -0.006(4) 0.001(4)
  O1 0.161(3) 0.060(3) 0.110(4) 0.031(2) -0.067(3) -0.021(3)
  C2 0.117(5) 0.079(5) 0.116(8) -0.003(4) -0.046(5) 0.002(5)
  C25 0.124(5) 0.082(5) 0.102(6) 0.041(4) 0.025(4) 0.007(5)
  C15 0.090(4) 0.045(3) 0.097(6) 0.001(3) -0.023(4) -0.003(4)
  C8 0.100(4) 0.048(4) 0.076(5) 0.006(3) -0.029(3) -0.007(3)
  C6 0.116(5) 0.074(4) 0.141(8) 0.007(4) -0.061(5) -0.005(5)
  C3 0.152(6) 0.083(5) 0.109(7) 0.000(4) -0.060(5) 0.017(5)
  C1 0.093(4) 0.057(4) 0.077(5) 0.015(3) -0.026(4) 0.001(4)
  C9 0.119(5) 0.054(4) 0.083(6) 0.011(3) -0.033(4) 0.006(4)
  C13 0.125(5) 0.091(5) 0.062(5) 0.037(4) -0.019(4) -0.001(4)
  C22 0.120(6) 0.104(6) 0.100(6) -0.003(4) 0.031(5) 0.008(6)
  C21 0.080(4) 0.084(5) 0.086(5) 0.009(3) 0.023(4) 0.003(4)
  C4 0.141(6) 0.099(6) 0.093(6) 0.044(5) -0.044(4) 0.013(5)
  C23 0.152(6) 0.081(5) 0.124(8) 0.010(5) 0.060(6) -0.016(6)
  C5 0.133(5) 0.089(6) 0.136(8) 0.020(4) -0.077(5) -0.033(5)
  C7 0.102(4) 0.053(4) 0.088(5) 0.003(3) -0.029(3) -0.007(4)
  C24 0.146(7) 0.084(5) 0.114(7) 0.038(4) 0.028(5) 0.002(6)
  F2 0.217(4) 0.069(2) 0.207(6) -0.012(3) -0.137(4) 0.028(3)
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 C10 . 1.747(6) yes
  S1 C8 . 1.763(6) yes
  N1 C10 . 1.299(6) ?
  N1 N3 . 1.386(5) yes
  N1 C9 . 1.394(7) yes
  C16 C17 . 1.396(7) ?
  C16 C15 . 1.408(7) ?
  C16 H16 . 0.9300 ?
  C14 C19 . 1.371(6) ?
  C14 C15 . 1.377(7) ?
  C14 C12 . 1.548(7) ?
  C11 N3 . 1.314(6) yes
  C11 N2 . 1.376(6) yes
  C11 C12 . 1.511(7) yes
  F1 C18 . 1.391(5) yes
  C17 C18 . 1.380(7) ?
  C17 C20 . 1.481(7) ?
  C19 C18 . 1.381(7) ?
  C19 H19 . 0.9300 ?
  N2 C10 . 1.296(6) ?
  C20 C25 . 1.372(7) ?
  C20 C21 . 1.384(7) ?
  C12 C13 . 1.496(7) ?
  C12 H12 . 0.9800 ?
  O1 C9 . 1.193(6) yes
  C2 F2 . 1.345(6) ?
  C2 C3 . 1.354(8) ?
  C2 C1 . 1.382(7) ?
  C25 C24 . 1.377(8) ?
  C25 H25 . 0.9300 ?
  C15 H15 . 0.9300 ?
  C8 C7 . 1.331(6) yes
  C8 C9 . 1.494(7) ?
  C6 C1 . 1.385(7) ?
  C6 C5 . 1.392(9) ?
  C6 H6 . 0.9300 ?
  C3 C4 . 1.337(8) ?
  C3 H3 . 0.9300 ?
  C1 C7 . 1.435(7) yes
  C13 H13C . 0.9600 ?
  C13 H13B . 0.9600 ?
  C13 H13A . 0.9600 ?
  C22 C23 . 1.369(8) ?
  C22 C21 . 1.407(8) ?
  C22 H22 . 0.9300 ?
  C21 H21 . 0.9300 ?
  C4 C5 . 1.363(8) ?
  C4 H4 . 0.9300 ?
  C23 C24 . 1.332(9) ?
  C23 H23 . 0.9300 ?
  C5 H5 . 0.9300 ?
  C7 H7 . 0.9300 ?
  C24 H24 . 0.9300 ?