#------------------------------------------------------------------------------
#$Date: 2008-01-26 14:05:32 +0100 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008179.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_2008179
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_publ_section_title
;
Ethyl 7-oxo-3-(4-tolyl)-4,5,6,6a,7,8-hexahydro-3H-cyclopenta-
[b][1,2,4]triazolo[4,3-a][1,5]benzodiazepine-1-carboxylate
and ethyl
3-(4-chlorophenyl)-8-methyl-7-oxo-4,5,6,6a,7,8-hexahydro-3H-cyclopenta-
[b][1,2,4]triazolo[4,3-a][1,5]benzodiazepine-1-carboxylate
;
loop_
_publ_author_name
  'Aatif, A.'
  'Baouid, A.'
  'Hasnaoui, A.'
  'Benharref, A.'
  'Alilou, E. H.'
  'Pierrot, M.'
_chemical_formula_sum  'C23 H24 N4 O3'
_chemical_formula_weight  404.47
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  +X,+Y,+Z
  -X,-Y,-Z
  -X,+Y+1/2,-Z+1/2
  +X,-Y+1/2,+Z+1/2
_cell_length_a  9.5570(10)
_cell_length_b  16.1400(10)
_cell_length_c  13.6880(10)
_cell_angle_alpha  90.0000(10)
_cell_angle_beta  100.9780(10)
_cell_angle_gamma  90.0000(10)
_cell_volume  2072.7(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.296
_refine_ls_R_factor_obs  0.061
_refine_ls_wR_factor_obs  0.087
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
  O1 0.56750(8) 0.10080(5) 0.51050(7) 0.0611(4) Uij 1.00
  O2 0.00710(8) 0.14310(5) 0.20710(7) 0.0629(4) Uij 1.00
  O3 -0.10720(9) 0.19030(7) 0.32400(8) 0.0866(6) Uij 1.00
  N1 0.36100(9) 0.24690(5) 0.37550(6) 0.0418(4) Uij 1.00
  N2 0.17340(9) 0.21560(5) 0.45000(7) 0.0457(4) Uij 1.00
  N3 0.24370(9) 0.22650(5) 0.30190(7) 0.0459(4) Uij 1.00
  N4 0.33890(9) 0.06740(5) 0.51260(7) 0.0464(5) Uij 1.00
  C1 0.44870(10)
  0.30980(7) 0.34410(7) 0.0424(5) Uij 1.00
  C2 0.59350(10)
  0.29720(7) 0.35550(8) 0.0520(6) Uij 1.00
  C3 0.67880(10)
  0.35990(9) 0.32720(9) 0.0618(7) Uij 1.00
  C4 0.62220(10)
  0.43350(8) 0.28780(9) 0.0605(7) Uij 1.00
  C5 0.47610(10)
  0.44370(8) 0.27310(9) 0.0575(6) Uij 1.00
  C6 0.38890(10)
  0.38250(7) 0.30040(9) 0.0514(6) Uij 1.00
  C7 0.31600(10)
  0.25320(6) 0.47500(8) 0.0423(5) Uij 1.00
  C8 0.41720(10)
  0.20670(7) 0.55790(8) 0.0459(5) Uij 1.00
  C9 0.54070(10)
  0.26600(8) 0.58890(8) 0.0566(6) Uij 1.00
  C10 0.4722(2) 0.35180(9) 0.57660(10)
  0.0740(8) Uij 1.00
  C11 0.31920(10)
  0.33990(7) 0.52020(9) 0.0589(7) Uij 1.00
  C12 0.12800(10)
  0.15490(6) 0.51460(8) 0.0461(5) Uij 1.00
  C13 0.20620(10)
  0.08260(6) 0.54150(8) 0.0433(5) Uij 1.00
  C14 0.44990(10)
  0.12150(7) 0.52520(8) 0.0448(5) Uij 1.00
  C15 0.00260(10)
  0.16870(7) 0.54900(10)
  0.0592(7) Uij 1.00
  C16 -0.04870(10)
  0.11020(8) 0.60630(10)
  0.0670(7) Uij 1.00
  C17 0.02510(10)
  0.03750(8) 0.62960(9) 0.0604(7) Uij 1.00
  C18 0.15160(10)
  0.02350(7) 0.59800(9) 0.0510(6) Uij 1.00
  C19 0.14330(10)
  0.20450(6) 0.34710(8) 0.0448(5) Uij 1.00
  C20 0.00080(10)
  0.17950(7) 0.29320(10)
  0.0544(6) Uij 1.00
  C21 -0.1293(2) 0.12050(10)
  0.14640(10)
  0.0855(9) Uij 1.00
  C22 -0.1068(2) 0.06520(10)
  0.0696(2) 0.136(2) Uij 1.00
  C23 0.7141(2) 0.50090(10)
  0.25770(10)
  0.0930(10)
  Uij 1.00
  H2 0.6340(10)
  0.2439(8) 0.3804(9) 0.059(3) Uiso 1.00
  H3 0.7810(10)
  0.3501(7) 0.3427(8) 0.050(3) Uiso 1.00
  H4 0.3640(10)
  0.0158(9) 0.5042(9) 0.050(3) Uiso 1.00
  H5 0.4340(10)
  0.4950(9) 0.2450(10)
  0.062(3) Uiso 1.00
  H6 0.287(2) 0.3906(8) 0.2882(9) 0.062(3) Uiso 1.00
  H8 0.3630(10)
  0.1976(7) 0.6160(10)
  0.058(3) Uiso 1.00
  H9A 0.6140(10)
  0.2569(8) 0.5400(10)
  0.061(3) Uiso 1.00
  H9B 0.5870(10)
  0.2552(7) 0.6570(10)
  0.050(3) Uiso 1.00
  H10A 0.4840(10)
  0.3799(8) 0.6385(9) 0.050(3) Uiso 1.00
  H10B 0.5180(10)
  0.3896(8) 0.5453(9) 0.050(3) Uiso 1.00
  H11A 0.2500(10)
  0.3367(7) 0.5666(9) 0.050(3) Uiso 1.00
  H11B 0.2820(10)
  0.3827(8) 0.4700(10)
  0.062(3) Uiso 1.00
  H15 -0.0550(10)
  0.2222(8) 0.5218(8) 0.050(5) Uiso 1.00
  H16 -0.1330(10)
  0.1195(7) 0.6316(9) 0.050(5) Uiso 1.00
  H17 -0.0120(10)
  -0.0022(8) 0.6695(9) 0.050(3) Uiso 1.00
  H18 0.2020(10)
  -0.0247(9) 0.6120(10)
  0.063(4) Uiso 1.00
  H21A -0.1820(10)
  0.0756(8) 0.1846(9) 0.050(8) Uiso 1.00
  H21B -0.1720(10)
  0.1710(8) 0.1328(9) 0.050(5) Uiso 1.00
  H22A -0.195(2) 0.0470(10)
  0.0300(10)
  0.050(6) Uiso 1.00
  H22B -0.056(3) 0.015(2) 0.097(2) 0.050(10)
  Uiso 1.00
  H22C -0.036(4) 0.111(2) 0.053(3) 0.05(2) Uiso 1.00
  H23A 0.711(2) 0.544(2) 0.289(2) 0.050(9) Uiso 1.00
  H23B 0.822(3) 0.4880(10)
  0.284(2) 0.050(8) Uiso 1.00
  H23C 0.721(2) 0.5010(10)
  0.1920(10)
  0.050(6) Uiso 1.00
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
  O1 0.0450(5) 0.0542(5) 0.0828(6) 0.0042(3) 0.0190(4) 0.0091(4)
  O2 0.0473(5) 0.0617(6) 0.0733(6) -.0007(4) -.0080(4) -.0081(5)
  O3 0.0419(6) 0.1171(9) 0.0980(8) 0.0061(5) 0.0130(5) -.0010(7)
  N1 0.0421(5) 0.0426(5) 0.0393(5) -.0046(3) 0.0084(4) -.0002(4)
  N2 0.0434(5) 0.0426(5) 0.0504(6) -.0014(4) 0.0143(4) 0.0018(4)
  N3 0.0467(5) 0.0420(5) 0.0464(5) -.0026(4) 0.0055(4) -.0018(4)
  N4 0.0442(5) 0.0389(5) 0.0551(6) 0.0009(4) 0.0152(4) -.0010(4)
  C1 0.0426(6) 0.0473(6) 0.0359(5) -.0053(4) 0.0081(4) -.0008(5)
  C2 0.0471(7) 0.0616(8) 0.0462(7) -.0015(5) 0.0133(5) -.0069(5)
  C3 0.0460(7) 0.0840(10)
  0.0558(7) -.0141(6) 0.0202(5) -.0175(7)
  C4 0.0692(8) 0.0624(8) 0.0510(7) -.0234(6) 0.0288(6) -.0168(6)
  C5 0.0688(8) 0.0521(7) 0.0502(7) -.0122(6) 0.0157(6) 0.0011(6)
  C6 0.0487(7) 0.0517(7) 0.0515(7) -.0057(5) 0.0080(5) 0.0052(5)
  C7 0.0448(6) 0.0369(6) 0.0444(6) -.0018(4) 0.0141(4) 0.0001(5)
  C8 0.0476(6) 0.0484(7) 0.0403(6) -.0061(5) 0.0106(5) 0.0004(5)
  C9 0.0625(7) 0.0619(8) 0.0418(7) -.0183(6) 0.0028(5) -.0008(5)
  C10 0.0810(10)
  0.0600(9) 0.0790(10)
  -.0237(7) 0.0236(7) -.0259(7)
  C11 0.0696(8) 0.0425(7) 0.0651(8) -.0018(5) 0.0284(6) -.0075(6)
  C12 0.0457(6) 0.0412(6) 0.0510(6) -.0034(5) 0.0172(5) -.0001(5)
  C13 0.0412(6) 0.0430(6) 0.0445(6) -.0043(4) 0.0109(4) -.0030(5)
  C14 0.0408(6) 0.0475(7) 0.0444(6) 0.0010(4) 0.0089(5) 0.0068(5)
  C15 0.0526(7) 0.0525(7) 0.0728(8) 0.0030(5) 0.0267(6) 0.0004(6)
  C16 0.0549(8) 0.0666(9) 0.0813(9) -.0047(6) 0.0359(7) -.0016(7)
  C17 0.0591(7) 0.0602(8) 0.0615(8) -.0152(6) 0.0217(6) 0.0038(6)
  C18 0.0490(7) 0.0457(7) 0.0562(7) -.0074(5) 0.0110(5) 0.0022(5)
  C19 0.0415(6) 0.0374(6) 0.0534(7) 0.0014(4) 0.0087(5) 0.0032(5)
  C20 0.0453(7) 0.0453(7) 0.0687(8) 0.0041(5) 0.0028(6) 0.0077(6)
  C21 0.0604(9) 0.0770(10)
  0.1070(10)
  -.0066(7) -.0271(8) -.0026(9)
  C22 0.118(2) 0.126(2) 0.142(2) 0.0080(10)
  -.0610(10)
  -.059(2)
  C23 0.1010(10)
  0.0870(10)
  0.0970(10)
  -.0459(9) 0.0640(10)
  -.0351(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C14 . . 1.225(2) ?
  O2 C20 . . 1.328(2) ?
  O2 C21 . . 1.453(2) ?
  O3 C20 . . 1.200(2) ?
  N1 N3 . . 1.396(2) ?
  N1 C1 . . 1.434(2) ?
  N1 C7 . . 1.508(2) ?
  N2 C7 . . 1.471(2) ?
  N2 C12 . . 1.441(2) ?
  N2 C19 . . 1.394(2) ?
  N3 C19 . . 1.287(2) ?
  N4 C13 . . 1.420(2) ?
  N4 C14 . . 1.359(2) ?
  C1 C2 . . 1.378(2) ?
  C1 C6 . . 1.390(2) ?
  C2 C3 . . 1.400(2) ?
  C3 C4 . . 1.372(2) ?
  C4 C5 . . 1.382(2) ?
  C4 C23 . . 1.504(3) ?
  C5 C6 . . 1.389(2) ?
  C7 C8 . . 1.539(2) ?
  C7 C11 . . 1.528(2) ?
  C8 C9 . . 1.516(2) ?
  C8 C14 . . 1.497(2) ?
  C9 C10 . . 1.527(2) ?
  C10 C11 . . 1.530(2) ?
  C12 C13 . . 1.397(2) ?
  C12 C15 . . 1.387(2) ?
  C13 C18 . . 1.391(2) ?
  C15 C16 . . 1.376(2) ?
  C16 C17 . . 1.375(2) ?
  C17 C18 . . 1.378(2) ?
  C19 C20 . . 1.476(2) ?
  C21 C22 . . 1.426(3) ?