#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012924.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_2012924
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o585
_journal_page_last  o588
_publ_section_title
;
Ethyl 5-[2-(2-aminoph\'enylimino)-2-ph\'enyl\'ethylid\`ene]-
4-(4-chloroph\'enyl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate et \'ethyl
5-{2-[2-(m\'ethylamino)ph\'enylimino]-2-ph\'enyl\'ethylid\`ene}-
4-(4-nitroph\'enyl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate
;
loop_
_publ_author_name
  'El Hazazi, S.'
  'Baouid, A.'
  'Hasnaoui, A.'
  'Pierrot, M.'
_chemical_formula_moiety  'C26 H23 N5 O4 S'
_chemical_formula_sum  'C26 H23 N5 O4 S'
_chemical_formula_structural  'C26 H23 N5 O4 S'
_chemical_formula_weight  501.55
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.7619(2)
_cell_length_b  10.7465(3)
_cell_length_c  12.1924(2)
_cell_angle_alpha  87.137(2)
_cell_angle_beta  83.151(2)
_cell_angle_gamma  75.4690(10)
_cell_volume  1229.10(10)
_cell_formula_units_Z  2
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.355
_diffrn_ambient_temperature  293
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 -0.16164(5) 0.06197(5) 0.12082(4) 0.03578(18) Uani d . 1 . . S
  O30 0.4718(4) 0.4284(4) 0.3144(2) 0.1291(13) Uani d . 1 . . O
  O31 0.5504(3) 0.4262(3) 0.1427(3) 0.1181(11) Uani d . 1 . . O
  O33 -0.2123(2) 0.31727(18) -0.12886(15) 0.0634(5) Uani d . 1 . . O
  O34 -0.32142(16) 0.16124(16) -0.06770(13) 0.0465(4) Uani d . 1 . . O
  N3 0.03640(17) 0.17858(15) 0.12328(14) 0.0334(4) Uani d . 1 . . N
  N4 -0.03416(17) 0.23641(15) 0.03665(14) 0.0351(4) Uani d . 1 . . N
  N8 -0.12750(18) -0.10683(16) 0.27964(14) 0.0376(4) Uani d . 1 . . N
  N15 -0.1320(2) -0.33740(18) 0.18938(15) 0.0474(5) Uani d . 1 . . N
  H15 -0.0634 -0.2872 0.1713 0.057 Uiso d R 1 . . H
  N29 0.4684(3) 0.4023(3) 0.2190(2) 0.0798(8) Uani d . 1 . . N
  C2 -0.00964(19) 0.07709(17) 0.17717(16) 0.0311(4) Uani d . 1 . . C
  C5 -0.1378(2) 0.18571(18) 0.02621(16) 0.0350(4) Uani d . 1 . . C
  C6 0.0547(2) -0.00127(17) 0.25688(16) 0.0335(4) Uani d . 1 . . C
  H6 0.1436 0.0085 0.2770 0.040 Uiso d R 1 . . H
  C7 -0.0081(2) -0.09875(17) 0.31167(16) 0.0314(4) Uani d . 1 . . C
  C9 -0.2175(2) -0.18124(18) 0.33199(16) 0.0333(4) Uani d . 1 . . C
  C10 -0.3123(2) -0.1363(2) 0.42328(18) 0.0438(5) Uani d . 1 . . C
  H10 -0.3047 -0.0602 0.4575 0.053 Uiso d R 1 . . H
  C11 -0.4150(2) -0.1993(2) 0.4659(2) 0.0517(6) Uani d . 1 . . C
  H11 -0.4795 -0.1666 0.5300 0.062 Uiso d R 1 . . H
  C12 -0.4247(2) -0.3082(2) 0.4149(2) 0.0482(5) Uani d . 1 . . C
  H12 -0.4988 -0.3524 0.4419 0.058 Uiso d R 1 . . H
  C13 -0.3316(2) -0.35462(19) 0.32341(18) 0.0398(5) Uani d . 1 . . C
  H13 -0.3420 -0.4306 0.2888 0.048 Uiso d R 1 . . H
  C14 -0.2259(2) -0.29352(18) 0.28045(16) 0.0339(4) Uani d . 1 . . C
  C16 -0.1072(3) -0.4663(2) 0.1511(2) 0.0659(7) Uani d . 1 . . C
  H16A -0.0414 -0.4788 0.0871 0.079 Uiso d R 1 . . H
  H16B -0.1982 -0.4803 0.1325 0.079 Uiso d R 1 . . H
  H16C -0.0761 -0.5259 0.2087 0.079 Uiso d R 1 . . H
  C17 0.06749(19) -0.17966(17) 0.39955(16) 0.0324(4) Uani d . 1 . . C
  C18 0.0722(2) -0.31039(19) 0.41198(19) 0.0425(5) Uani d . 1 . . C
  H18 0.0239 -0.3494 0.3627 0.051 Uiso d R 1 . . H
  C19 0.1431(3) -0.3829(2) 0.4948(2) 0.0516(6) Uani d . 1 . . C
  H19 0.1434 -0.4729 0.5023 0.062 Uiso d R 1 . . H
  C20 0.2079(2) -0.3265(2) 0.5663(2) 0.0500(6) Uani d . 1 . . C
  H20 0.2529 -0.3771 0.6241 0.060 Uiso d R 1 . . H
  C21 0.2045(2) -0.1979(2) 0.55457(18) 0.0434(5) Uani d . 1 . . C
  H21 0.2482 -0.1590 0.6049 0.052 Uiso d R 1 . . H
  C22 0.1361(2) -0.12521(19) 0.47100(17) 0.0359(4) Uani d . 1 . . C
  H22 0.1365 -0.0361 0.4615 0.043 Uiso d R 1 . . H
  C23 0.1488(2) 0.23049(17) 0.15018(16) 0.0321(4) Uani d . 1 . . C
  C24 0.1614(2) 0.25275(19) 0.25859(17) 0.0394(5) Uani d . 1 . . C
  H24 0.0988 0.2284 0.3167 0.047 Uiso d R 1 . . H
  C25 0.2670(3) 0.3093(2) 0.2817(2) 0.0493(5) Uani d . 1 . . C
  H25 0.2817 0.3269 0.3558 0.059 Uiso d R 1 . . H
  C26 0.3557(2) 0.3426(2) 0.1946(2) 0.0498(6) Uani d . 1 . . C
  C27 0.3433(3) 0.3225(3) 0.0868(2) 0.0538(6) Uani d . 1 . . C
  H27 0.4107 0.3479 0.0299 0.065 Uiso d R 1 . . H
  C28 0.2392(2) 0.2647(2) 0.06381(18) 0.0431(5) Uani d . 1 . . C
  H28 0.2309 0.2491 -0.0113 0.052 Uiso d R 1 . . H
  C32 -0.2279(2) 0.2318(2) -0.06558(18) 0.0412(5) Uani d . 1 . . C
  C35 -0.4081(3) 0.1871(2) -0.1601(2) 0.0503(6) Uani d . 1 . . C
  H35A -0.4761 0.2674 -0.1489 0.060 Uiso d R 1 . . H
  H35B -0.3453 0.1927 -0.2268 0.060 Uiso d R 1 . . H
  C36 -0.4759(3) 0.0777(3) -0.1633(3) 0.0648(7) Uani d . 1 . . C
  H36A -0.5333 0.0886 -0.2230 0.078 Uiso d R 1 . . H
  H36B -0.5335 0.0739 -0.0945 0.078 Uiso d R 1 . . H
  H36C -0.4027 -0.0008 -0.1723 0.078 Uiso d R 1 . . H
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 0.0361(3) 0.0390(3) 0.0388(3) -0.0189(2) -0.0128(2) 0.00708(19)
  O30 0.165(3) 0.192(3) 0.093(2) -0.146(3) -0.057(2) 0.0243(19)
  O31 0.0950(18) 0.177(3) 0.119(2) -0.106(2) 0.0000(16) -0.0086(19)
  O33 0.0764(12) 0.0653(11) 0.0594(12) -0.0323(9) -0.0320(9) 0.0292(9)
  O34 0.0421(8) 0.0608(9) 0.0429(9) -0.0194(7) -0.0205(6) 0.0104(7)
  N3 0.0361(8) 0.0329(8) 0.0361(9) -0.0157(7) -0.0124(6) 0.0090(6)
  N4 0.0380(9) 0.0356(8) 0.0348(9) -0.0128(7) -0.0114(7) 0.0077(6)
  N8 0.0416(9) 0.0365(8) 0.0424(10) -0.0211(7) -0.0156(7) 0.0117(7)
  N15 0.0600(12) 0.0468(10) 0.0406(11) -0.0255(9) 0.0008(8) -0.0024(8)
  N29 0.0788(17) 0.098(2) 0.089(2) -0.0646(16) -0.0301(15) 0.0140(15)
  C2 0.0326(9) 0.0295(9) 0.0344(10) -0.0131(7) -0.0056(7) 0.0019(7)
  C5 0.0367(10) 0.0360(10) 0.0346(11) -0.0120(8) -0.0087(8) 0.0037(7)
  C6 0.0332(9) 0.0320(9) 0.0397(11) -0.0142(7) -0.0106(8) 0.0054(7)
  C7 0.0344(9) 0.0287(9) 0.0337(10) -0.0120(7) -0.0075(7) 0.0030(7)
  C9 0.0346(10) 0.0352(9) 0.0355(11) -0.0160(8) -0.0140(7) 0.0097(7)
  C10 0.0470(12) 0.0428(11) 0.0457(13) -0.0160(9) -0.0105(9) -0.0017(9)
  C11 0.0447(12) 0.0611(14) 0.0485(14) -0.0161(10) 0.0028(10) 0.0013(10)
  C12 0.0387(11) 0.0519(13) 0.0581(15) -0.0218(10) -0.0043(9) 0.0125(10)
  C13 0.0428(11) 0.0328(10) 0.0503(12) -0.0185(8) -0.0170(9) 0.0113(8)
  C14 0.0386(10) 0.0325(9) 0.0346(11) -0.0144(8) -0.0127(8) 0.0097(7)
  C16 0.089(2) 0.0429(13) 0.0577(17) -0.0087(13) 0.0068(14) -0.0010(11)
  C17 0.0310(9) 0.0322(9) 0.0349(10) -0.0101(7) -0.0055(7) 0.0054(7)
  C18 0.0466(12) 0.0329(10) 0.0518(13) -0.0133(8) -0.0161(9) 0.0069(8)
  C19 0.0563(14) 0.0346(11) 0.0660(16) -0.0132(10) -0.0192(11) 0.0176(10)
  C20 0.0456(12) 0.0541(13) 0.0506(14) -0.0118(10) -0.0171(10) 0.0201(10)
  C21 0.0389(11) 0.0528(12) 0.0419(13) -0.0150(9) -0.0132(9) 0.0055(9)
  C22 0.0349(10) 0.0360(10) 0.0392(11) -0.0122(8) -0.0082(8) 0.0044(7)
  C23 0.0318(9) 0.0286(9) 0.0394(11) -0.0124(7) -0.0100(7) 0.0054(7)
  C24 0.0447(11) 0.0394(10) 0.0394(12) -0.0202(9) -0.0072(8) 0.0039(8)
  C25 0.0599(14) 0.0522(13) 0.0467(14) -0.0290(11) -0.0181(10) 0.0019(9)
  C26 0.0471(13) 0.0532(13) 0.0608(15) -0.0307(11) -0.0172(10) 0.0079(10)
  C27 0.0447(12) 0.0702(16) 0.0555(15) -0.0335(12) -0.0040(10) 0.0084(11)
  C28 0.0425(11) 0.0544(12) 0.0374(12) -0.0220(9) -0.0043(8) 0.0028(9)
  C32 0.0412(11) 0.0447(11) 0.0400(12) -0.0121(9) -0.0127(9) 0.0059(8)
  C35 0.0450(12) 0.0601(14) 0.0471(14) -0.0069(10) -0.0250(10) 0.0018(10)
  C36 0.0545(15) 0.0682(17) 0.0769(19) -0.0116(12) -0.0358(14) -0.0011(13)
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 C2 . 1.7537(18) yes
  S1 C5 . 1.7582(19) yes
  O30 N29 . 1.216(4) ?
  O31 N29 . 1.214(4) ?
  O33 C32 . 1.198(3) ?
  O34 C32 . 1.328(3) ?
  O34 C35 . 1.463(2) ?
  N3 N4 . 1.367(2) yes
  N3 C2 . 1.388(2) yes
  N3 C23 . 1.426(2) ?
  N4 C5 . 1.285(2) yes
  N8 C7 . 1.296(2) yes
  N8 C9 . 1.410(2) yes
  N15 C14 . 1.374(3) ?
  N15 C16 . 1.437(3) ?
  N15 H15 . 0.9601 ?
  N29 C26 . 1.471(3) ?
  C2 C6 . 1.359(3) yes
  C5 C32 . 1.494(3) ?
  C6 C7 . 1.440(2) yes
  C6 H6 . 0.9611 ?
  C7 C17 . 1.491(2) ?
  C9 C10 . 1.383(3) ?
  C9 C14 . 1.413(3) ?
  C10 C11 . 1.384(3) ?
  C10 H10 . 0.9591 ?
  C11 C12 . 1.381(3) ?
  C11 H11 . 0.9642 ?
  C12 C13 . 1.380(3) ?
  C12 H12 . 0.9784 ?
  C13 C14 . 1.395(3) ?
  C13 H13 . 0.9708 ?
  C16 H16A . 0.9419 ?
  C16 H16B . 0.9908 ?
  C16 H16C . 0.9508 ?
  C17 C22 . 1.391(3) ?
  C17 C18 . 1.395(3) ?
  C18 C19 . 1.387(3) ?
  C18 H18 . 0.9752 ?
  C19 C20 . 1.379(3) ?
  C19 H19 . 0.9663 ?
  C20 C21 . 1.375(3) ?
  C20 H20 . 0.9492 ?
  C21 C22 . 1.384(3) ?
  C21 H21 . 0.9542 ?
  C22 H22 . 0.9595 ?
  C23 C24 . 1.380(3) ?
  C23 C28 . 1.387(3) ?
  C24 C25 . 1.383(3) ?
  C24 H24 . 0.9501 ?
  C25 C26 . 1.380(3) ?
  C25 H25 . 0.9665 ?
  C26 C27 . 1.366(4) ?
  C27 C28 . 1.379(3) ?
  C27 H27 . 0.9751 ?
  C28 H28 . 0.9557 ?
  C35 C36 . 1.492(4) ?
  C35 H35A . 0.9521 ?
  C35 H35B . 0.9672 ?
  C36 H36A . 0.9557 ?
  C36 H36B . 0.9576 ?
  C36 H36C . 0.9604 ?
_cod_database_code 2012924