#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008839.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_2008839
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_publ_section_title
;
Substituted clonidine derivatives. II.
Ethyl 3,5-dichloro-4-(1-isobutyrylimidazolidin-2-ylideneamino)benzoate and
ethyl 3,5-dichloro-4-(1,3-diisobutyrylimidazolidin-2-ylideneamino)benzoate
;
loop_
_publ_author_name
  'E. M. Elssfah'
  'K. Chinnakali'
  'H.-K. Fun'
  'I. W. Mathison'
  'E. K. Gan'
  'M. Zubaid'
  'T. W. Sam'
  'K. S. Khoo'
_chemical_formula_sum  'C16 H19 Cl2 N3 O3'
_chemical_formula_weight  372.24
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
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  13.6707(10)
_cell_length_b  10.4841(10)
_cell_length_c  13.9479(12)
_cell_angle_alpha  90.00
_cell_angle_beta  115.943(6)
_cell_angle_gamma  90.00
_cell_volume  1797.6(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.375
_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
  Cl1 0.57899(4) 0.75780(5) 0.14267(4) 0.05864(16) Uani d . 1 . . Cl
  Cl2 0.33308(4) 1.08679(6) 0.24195(3) 0.06105(17) Uani d . 1 . . Cl
  O1 0.74299(10) 0.80060(13) 0.60017(9) 0.0509(3) Uani d . 1 . . O
  O2 0.27206(12) 0.94372(14) -0.22036(10) 0.0592(4) Uani d . 1 . . O
  O3 0.17930(11) 1.08271(13) -0.16873(9) 0.0511(3) Uani d . 1 . . O
  N1 0.52145(12) 0.91326(14) 0.29179(10) 0.0471(4) Uani d . 1 . . N
  N2 0.44445(13) 0.71847(16) 0.31030(13) 0.0517(4) Uani d . 1 . . N
  N3 0.59200(11) 0.78862(14) 0.44809(10) 0.0405(3) Uani d . 1 . . N
  C1 0.45151(13) 0.92568(16) 0.18316(12) 0.0391(4) Uani d . 1 . . C
  C2 0.47113(14) 0.86446(16) 0.10417(13) 0.0415(4) Uani d . 1 . . C
  C3 0.40803(15) 0.88699(17) -0.00300(13) 0.0430(4) Uani d . 1 . . C
  C4 0.32291(13) 0.97260(16) -0.03470(12) 0.0390(4) Uani d . 1 . . C
  C5 0.30096(14) 1.03534(18) 0.04108(12) 0.0406(4) Uani d . 1 . . C
  C6 0.36429(14) 1.01054(17) 0.14833(12) 0.0406(4) Uani d . 1 . . C
  C7 0.51702(13) 0.81412(16) 0.34190(12) 0.0381(4) Uani d . 1 . . C
  C8 0.4692(2) 0.6184(3) 0.38767(19) 0.0708(7) Uani d . 1 . . C
  C9 0.55923(17) 0.6732(2) 0.48618(15) 0.0509(5) Uani d . 1 . . C
  C10 0.68837(13) 0.84877(17) 0.51308(11) 0.0382(4) Uani d . 1 . . C
  C11 0.72041(16) 0.96961(19) 0.47722(14) 0.0506(5) Uani d . 1 . . C
  C12 0.6614(3) 1.0809(2) 0.4987(2) 0.0821(8) Uani d . 1 . . C
  H12A 0.5843 1.0683 0.4605 0.123 Uiso calc R 1 . . H
  H12B 0.6813 1.1588 0.4755 0.123 Uiso calc R 1 . . H
  H12C 0.6815 1.0859 0.5737 0.123 Uiso calc R 1 . . H
  C13 0.84432(19) 0.9849(3) 0.53241(19) 0.0874(9) Uani d . 1 . . C
  H13A 0.8776 0.9128 0.5161 0.131 Uiso calc R 1 . . H
  H13B 0.8686 0.9900 0.6081 0.131 Uiso calc R 1 . . H
  H13C 0.8643 1.0614 0.5076 0.131 Uiso calc R 1 . . H
  C14 0.25691(14) 0.99600(17) -0.15102(12) 0.0425(4) Uani d . 1 . . C
  C15 0.11407(18) 1.1198(2) -0.27931(14) 0.0566(5) Uani d . 1 . . C
  C16 0.03463(18) 1.2152(2) -0.27872(17) 0.0653(6) Uani d . 1 . . C
  H16A -0.0118 1.2405 -0.3506 0.098 Uiso calc R 1 . . H
  H16B 0.0727 1.2884 -0.2383 0.098 Uiso calc R 1 . . H
  H16C -0.0085 1.1786 -0.2469 0.098 Uiso calc R 1 . . H
  H1N2 0.3907(17) 0.7174(19) 0.2510(17) 0.052(6) Uiso d . 1 . . H
  H3 0.4242(18) 0.846(2) -0.0538(17) 0.066(6) Uiso d . 1 . . H
  H5 0.2471(17) 1.0961(19) 0.0236(15) 0.051(6) Uiso d . 1 . . H
  H8A 0.405(2) 0.603(2) 0.399(2) 0.085(8) Uiso d . 1 . . H
  H8B 0.479(3) 0.538(4) 0.360(2) 0.131(13) Uiso d . 1 . . H
  H9A 0.6219(18) 0.616(2) 0.5193(16) 0.063(6) Uiso d . 1 . . H
  H9B 0.5345(18) 0.699(2) 0.5408(18) 0.067(6) Uiso d . 1 . . H
  H11 0.7012(17) 0.965(2) 0.4045(16) 0.057(6) Uiso d . 1 . . H
  H15A 0.081(2) 1.045(2) -0.3195(19) 0.080(8) Uiso d . 1 . . H
  H15B 0.170(2) 1.153(2) -0.3055(18) 0.081(7) Uiso d . 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 0.0483(3) 0.0511(3) 0.0621(3) 0.0132(2) 0.0108(2) 0.0074(2)
  Cl2 0.0554(3) 0.0879(4) 0.0380(2) 0.0081(3) 0.0187(2) -0.0022(2)
  O1 0.0449(7) 0.0616(8) 0.0317(5) 0.0075(6) 0.0033(5) 0.0063(6)
  O2 0.0659(9) 0.0658(9) 0.0361(6) 0.0098(7) 0.0134(6) -0.0020(6)
  O3 0.0470(7) 0.0650(8) 0.0313(6) 0.0124(6) 0.0078(5) 0.0087(6)
  N1 0.0433(8) 0.0474(8) 0.0319(6) -0.0076(7) -0.0008(6) 0.0089(6)
  N2 0.0424(8) 0.0530(9) 0.0424(8) -0.0143(7) 0.0024(7) 0.0099(7)
  N3 0.0358(7) 0.0431(8) 0.0334(6) -0.0006(6) 0.0069(6) 0.0103(6)
  C1 0.0353(8) 0.0387(9) 0.0318(7) -0.0089(7) 0.0042(6) 0.0054(6)
  C2 0.0362(8) 0.0351(8) 0.0428(8) 0.0007(7) 0.0076(7) 0.0077(7)
  C3 0.0441(10) 0.0428(10) 0.0367(8) -0.0013(8) 0.0126(7) -0.0007(7)
  C4 0.0381(9) 0.0412(9) 0.0315(7) -0.0025(7) 0.0095(6) 0.0051(7)
  C5 0.0345(8) 0.0458(9) 0.0346(7) 0.0027(8) 0.0088(7) 0.0074(7)
  C6 0.0377(8) 0.0477(10) 0.0321(7) -0.0056(8) 0.0113(6) 0.0026(7)
  C7 0.0316(8) 0.0424(9) 0.0322(7) 0.0009(7) 0.0066(6) 0.0039(7)
  C8 0.0645(15) 0.0643(15) 0.0604(12) -0.0214(12) 0.0059(11) 0.0216(11)
  C9 0.0461(11) 0.0512(11) 0.0477(10) 0.0025(9) 0.0133(8) 0.0180(9)
  C10 0.0335(8) 0.0463(9) 0.0286(7) 0.0050(7) 0.0078(6) -0.0017(7)
  C11 0.0467(10) 0.0554(11) 0.0349(8) -0.0105(9) 0.0041(7) 0.0003(8)
  C12 0.116(2) 0.0480(12) 0.0674(14) 0.0001(14) 0.0262(14) -0.0023(11)
  C13 0.0553(14) 0.108(2) 0.0699(14) -0.0328(14) 0.0002(11) 0.0124(14)
  C14 0.0420(9) 0.0457(10) 0.0323(8) -0.0029(8) 0.0092(7) 0.0028(7)
  C15 0.0539(12) 0.0678(14) 0.0321(8) 0.0085(11) 0.0039(8) 0.0107(9)
  C16 0.0609(13) 0.0647(13) 0.0527(11) 0.0122(11) 0.0087(10) 0.0104(10)
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 C2 . 1.7379(18) ?
  Cl2 C6 . 1.7360(18) ?
  O1 C10 . 1.222(2) yes
  O2 C14 . 1.206(2) yes
  O3 C14 . 1.336(2) yes
  O3 C15 . 1.457(2) yes
  N1 C7 . 1.269(2) yes
  N1 C1 . 1.400(2) yes
  N2 C7 . 1.342(2) yes
  N2 C8 . 1.436(3) yes
  N3 C10 . 1.382(2) yes
  N3 C7 . 1.410(2) yes
  N3 C9 . 1.468(2) yes
  C1 C6 . 1.394(2) ?
  C1 C2 . 1.399(3) ?
  C2 C3 . 1.381(2) ?
  C3 C4 . 1.380(3) ?
  C4 C5 . 1.385(2) ?
  C4 C14 . 1.492(2) ?
  C5 C6 . 1.386(2) ?
  C8 C9 . 1.501(3) ?
  C10 C11 . 1.496(3) ?
  C11 C12 . 1.521(3) ?
  C11 C13 . 1.532(3) ?
  C15 C16 . 1.479(3) ?