#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012923.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_2012923
_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  'C25 H21 Cl N4 O2 S'
_chemical_formula_sum  'C25 H21 Cl N4 O2 S'
_chemical_formula_structural  'C25 H21 Cl N4 O2 S'
_chemical_formula_weight  476.97
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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  9.98260(10)
_cell_length_b  9.5040(2)
_cell_length_c  25.0790(10)
_cell_angle_alpha  90
_cell_angle_beta  90.667(5)
_cell_angle_gamma  90
_cell_volume  2379.30(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.332
_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
  Cl1 0.39057(8) 0.44576(11) 0.59178(4) 0.0919(3) Uani d . 1 . . Cl
  S1 1.14515(5) 0.15588(5) 0.492347(19) 0.04240(17) Uani d . 1 . . S
  O29 1.1594(2) 0.0109(2) 0.64135(7) 0.0748(6) Uani d . 1 . . O
  O30 1.29502(16) -0.01495(17) 0.57121(7) 0.0552(4) Uani d . 1 . . O
  N3 0.92569(16) 0.23524(17) 0.53462(6) 0.0395(4) Uani d . 1 . . N
  N4 0.98853(18) 0.16191(17) 0.57447(6) 0.0418(4) Uani d . 1 . . N
  N8 1.13385(19) 0.2502(2) 0.39102(7) 0.0505(4) Uani d . 1 . . N
  N15 1.2142(3) 0.0176(3) 0.33324(11) 0.0855(8) Uani d . 1 . . N
  H15A 1.1303 0.0153 0.3471 0.103 Uiso d R 1 . . H
  H15B 1.2258 -0.0560 0.3099 0.103 Uiso d R 1 . . H
  C2 0.99095(19) 0.24284(19) 0.48607(7) 0.0370(4) Uani d . 1 . . C
  C5 1.1025(2) 0.1164(2) 0.55829(8) 0.0413(4) Uani d . 1 . . C
  C6 0.9427(2) 0.3049(2) 0.44103(7) 0.0417(4) Uani d . 1 . . C
  H6 0.8555 0.3471 0.4420 0.050 Uiso d R 1 . . H
  C7 1.0178(2) 0.3097(2) 0.39246(7) 0.0408(4) Uani d . 1 . . C
  C9 1.2198(2) 0.2686(3) 0.34702(8) 0.0519(5) Uani d . 1 . . C
  C10 1.2707(3) 0.3993(3) 0.33380(10) 0.0611(6) Uani d . 1 . . C
  H10 1.2377 0.4817 0.3515 0.073 Uiso d R 1 . . H
  C11 1.3678(3) 0.4127(4) 0.29511(13) 0.0800(8) Uani d . 1 . . C
  H11 1.4063 0.5025 0.2868 0.096 Uiso d R 1 . . H
  C12 1.4110(3) 0.2940(4) 0.26860(13) 0.0888(10) Uani d . 1 . . C
  H12 1.4778 0.3011 0.2415 0.107 Uiso d R 1 . . H
  C13 1.3591(3) 0.1647(4) 0.28033(12) 0.0782(9) Uani d . 1 . . C
  H13 1.3883 0.0828 0.2614 0.094 Uiso d R 1 . . H
  C14 1.2630(3) 0.1487(3) 0.31950(9) 0.0619(7) Uani d . 1 . . C
  C16 0.9523(2) 0.3850(2) 0.34670(7) 0.0416(4) Uani d . 1 . . C
  C17 0.9295(3) 0.3169(3) 0.29856(9) 0.0584(6) Uani d . 1 . . C
  H17 0.9596 0.2218 0.2938 0.070 Uiso d R 1 . . H
  C18 0.8637(3) 0.3882(3) 0.25742(10) 0.0735(8) Uani d . 1 . . C
  H18 0.8464 0.3412 0.2241 0.088 Uiso d R 1 . . H
  C19 0.8241(3) 0.5261(3) 0.26377(11) 0.0719(8) Uani d . 1 . . C
  H19 0.7769 0.5742 0.2356 0.086 Uiso d R 1 . . H
  C20 0.8500(3) 0.5936(3) 0.31084(11) 0.0679(7) Uani d . 1 . . C
  H20 0.8255 0.6907 0.3148 0.081 Uiso d R 1 . . H
  C21 0.9125(2) 0.5232(2) 0.35239(9) 0.0542(5) Uani d . 1 . . C
  H21 0.9284 0.5701 0.3858 0.065 Uiso d R 1 . . H
  C22 0.79537(19) 0.2877(2) 0.54588(7) 0.0388(4) Uani d . 1 . . C
  C23 0.7605(2) 0.4244(2) 0.53387(8) 0.0442(4) Uani d . 1 . . C
  H23 0.8227 0.4857 0.5164 0.053 Uiso d R 1 . . H
  C24 0.6339(2) 0.4728(2) 0.54702(9) 0.0539(5) Uani d . 1 . . C
  H24 0.6063 0.5669 0.5385 0.065 Uiso d R 1 . . H
  C25 0.5470(2) 0.3849(3) 0.57253(9) 0.0566(6) Uani d . 1 . . C
  C26 0.5822(3) 0.2496(3) 0.58504(12) 0.0681(7) Uani d . 1 . . C
  H26 0.5192 0.1904 0.6030 0.082 Uiso d R 1 . . H
  C27 0.7066(2) 0.1994(3) 0.57114(11) 0.0575(6) Uani d . 1 . . C
  H27 0.7314 0.1042 0.5793 0.069 Uiso d R 1 . . H
  C28 1.1870(2) 0.0327(2) 0.59589(8) 0.0479(5) Uani d . 1 . . C
  C31 1.3844(3) -0.1040(3) 0.60327(11) 0.0650(7) Uani d . 1 . . C
  H31A 1.4225 -0.0486 0.6317 0.078 Uiso d R 1 . . H
  H31B 1.3339 -0.1802 0.6181 0.078 Uiso d R 1 . . H
  C32 1.4901(3) -0.1541(3) 0.56716(14) 0.0840(10) Uani d . 1 . . C
  H32A 1.5521 -0.2132 0.5863 0.101 Uiso d R 1 . . H
  H32B 1.5371 -0.0753 0.5524 0.101 Uiso d R 1 . . H
  H32C 1.4485 -0.2070 0.5389 0.101 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
  Cl1 0.0518(5) 0.1405(7) 0.0840(5) 0.0379(4) 0.0215(3) 0.0085(5)
  S1 0.0385(3) 0.0508(3) 0.0379(3) 0.01371(18) 0.00110(18) 0.00082(18)
  O29 0.0809(14) 0.0970(13) 0.0464(10) 0.0325(10) -0.0028(9) 0.0179(9)
  O30 0.0477(10) 0.0602(9) 0.0574(9) 0.0202(7) -0.0065(7) 0.0105(7)
  N3 0.0370(9) 0.0478(9) 0.0336(8) 0.0116(6) 0.0012(6) 0.0053(6)
  N4 0.0440(10) 0.0465(9) 0.0349(8) 0.0100(6) -0.0019(6) 0.0046(6)
  N8 0.0495(11) 0.0693(11) 0.0327(8) 0.0191(8) 0.0027(7) 0.0021(7)
  N15 0.125(2) 0.0682(14) 0.0641(14) 0.0287(14) 0.0220(15) 0.0048(11)
  C2 0.0357(10) 0.0415(9) 0.0337(9) 0.0057(7) 0.0009(7) -0.0021(7)
  C5 0.0421(11) 0.0435(9) 0.0383(9) 0.0080(8) -0.0030(7) 0.0015(7)
  C6 0.0377(11) 0.0520(10) 0.0353(9) 0.0102(8) -0.0002(7) 0.0020(7)
  C7 0.0412(11) 0.0492(10) 0.0321(9) 0.0068(8) -0.0028(7) -0.0010(7)
  C9 0.0437(13) 0.0793(15) 0.0326(9) 0.0201(10) -0.0006(8) 0.0011(9)
  C10 0.0550(15) 0.0804(16) 0.0480(12) 0.0034(11) 0.0062(10) -0.0039(11)
  C11 0.069(2) 0.104(2) 0.0679(17) -0.0086(15) 0.0181(14) 0.0001(15)
  C12 0.071(2) 0.129(3) 0.0670(18) 0.0141(18) 0.0329(15) 0.0000(18)
  C13 0.079(2) 0.101(2) 0.0551(15) 0.0373(17) 0.0191(14) -0.0034(14)
  C14 0.0674(17) 0.0786(16) 0.0397(11) 0.0298(12) 0.0051(10) 0.0033(10)
  C16 0.0338(11) 0.0557(11) 0.0352(9) -0.0001(8) -0.0020(7) 0.0068(8)
  C17 0.0711(17) 0.0609(13) 0.0428(11) -0.0149(11) -0.0138(10) 0.0036(9)
  C18 0.0765(19) 0.100(2) 0.0436(12) -0.0312(16) -0.0210(12) 0.0106(13)
  C19 0.0508(16) 0.101(2) 0.0638(16) 0.0008(13) -0.0078(11) 0.0373(15)
  C20 0.0600(17) 0.0817(17) 0.0622(15) 0.0236(12) 0.0112(12) 0.0257(13)
  C21 0.0524(14) 0.0645(13) 0.0459(11) 0.0170(10) 0.0068(9) 0.0066(9)
  C22 0.0350(11) 0.0464(10) 0.0349(8) 0.0075(7) 0.0018(7) 0.0015(7)
  C23 0.0431(12) 0.0453(10) 0.0442(10) 0.0081(8) 0.0060(8) -0.0004(8)
  C24 0.0536(14) 0.0565(12) 0.0519(12) 0.0209(10) 0.0062(9) -0.0012(9)
  C25 0.0386(13) 0.0819(15) 0.0494(12) 0.0156(10) 0.0066(9) -0.0017(11)
  C26 0.0464(15) 0.0820(17) 0.0761(17) 0.0022(11) 0.0167(12) 0.0195(13)
  C27 0.0475(14) 0.0564(12) 0.0691(15) 0.0073(9) 0.0109(10) 0.0170(11)
  C28 0.0476(13) 0.0510(11) 0.0449(11) 0.0114(9) -0.0070(9) 0.0035(8)
  C31 0.0615(17) 0.0611(14) 0.0720(16) 0.0258(11) -0.0212(12) 0.0053(11)
  C32 0.073(2) 0.0857(19) 0.092(2) 0.0425(15) -0.0267(17) -0.0159(16)
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
  Cl1 C25 . 1.739(2) ?
  S1 C2 . 1.7526(19) yes
  S1 C5 . 1.753(2) yes
  O29 C28 . 1.194(3) ?
  O30 C28 . 1.329(3) ?
  O30 C31 . 1.463(2) ?
  N3 N4 . 1.365(2) yes
  N3 C2 . 1.389(2) yes
  N3 C22 . 1.425(2) ?
  N4 C5 . 1.287(3) yes
  N8 C7 . 1.290(3) yes
  N8 C9 . 1.417(3) yes
  N15 C14 . 1.383(4) ?
  N15 H15A . 0.9112 ?
  N15 H15B . 0.9196 ?
  C2 C6 . 1.358(3) yes
  C5 C28 . 1.488(3) ?
  C6 C7 . 1.439(3) yes
  C6 H6 . 0.9590 ?
  C7 C16 . 1.497(3) ?
  C9 C10 . 1.384(4) ?
  C9 C14 . 1.403(3) ?
  C10 C11 . 1.385(4) ?
  C10 H10 . 0.9604 ?
  C11 C12 . 1.381(5) ?
  C11 H11 . 0.9599 ?
  C12 C13 . 1.367(5) ?
  C12 H12 . 0.9599 ?
  C13 C14 . 1.390(4) ?
  C13 H13 . 0.9590 ?
  C16 C21 . 1.380(3) ?
  C16 C17 . 1.386(3) ?
  C17 C18 . 1.393(4) ?
  C17 H17 . 0.9604 ?
  C18 C19 . 1.378(5) ?
  C18 H18 . 0.9614 ?
  C19 C20 . 1.366(4) ?
  C19 H19 . 0.9606 ?
  C20 C21 . 1.381(3) ?
  C20 H20 . 0.9602 ?
  C21 H21 . 0.9604 ?
  C22 C23 . 1.377(3) ?
  C22 C27 . 1.380(3) ?
  C23 C24 . 1.388(3) ?
  C23 H23 . 0.9608 ?
  C24 C25 . 1.369(4) ?
  C24 H24 . 0.9591 ?
  C25 C26 . 1.368(4) ?
  C26 C27 . 1.379(4) ?
  C26 H26 . 0.9600 ?
  C27 H27 . 0.9595 ?
  C31 C32 . 1.478(4) ?
  C31 H31A . 0.9609 ?
  C31 H31B . 0.9597 ?
  C32 H32A . 0.9605 ?
  C32 H32B . 0.9601 ?
  C32 H32C . 0.9592 ?