#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008840.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_2008840
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_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  'C20 H25 Cl2 N3 O4'
_chemical_formula_weight  442.33
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  '-x, -y, -z'
  'x, -y, z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z+1/2'
_cell_length_a  42.7786(3)
_cell_length_b  9.2896(2)
_cell_length_c  22.7485(3)
_cell_angle_alpha  90.00
_cell_angle_beta  104.4070(10)
_cell_angle_gamma  90.00
_cell_volume  8755.9(2)
_cell_formula_units_Z  16
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.342
_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
  Cl1A -0.12112(3) -0.43144(15) 0.37303(6) 0.0743(4) Uani d . 1 . . Cl
  Cl2A -0.21037(3) -0.05323(12) 0.25321(6) 0.0682(4) Uani d . 1 . . Cl
  N1A -0.18341(8) -0.2613(4) 0.35005(16) 0.0500(9) Uani d . 1 . . N
  N2A -0.20014(8) -0.5099(4) 0.32742(17) 0.0513(9) Uani d . 1 . . N
  N3A -0.20626(9) -0.4043(4) 0.41295(18) 0.0597(11) Uani d . 1 . . N
  O1A -0.21875(10) -0.3655(4) 0.50110(18) 0.0923(12) Uani d . 1 . . O
  O2A -0.11598(9) -0.0793(5) 0.13937(17) 0.0938(13) Uani d . 1 . . O
  O3A -0.07962(8) -0.2323(4) 0.19358(14) 0.0675(9) Uani d . 1 . . O
  O4A -0.21021(8) -0.4150(3) 0.23264(14) 0.0701(10) Uani d . 1 . . O
  C1A -0.16532(10) -0.2449(4) 0.30798(18) 0.0440(10) Uani d . 1 . . C
  C2A -0.13536(10) -0.3132(4) 0.31349(19) 0.0485(11) Uani d . 1 . . C
  C3A -0.11660(10) -0.2861(5) 0.27370(19) 0.0519(12) Uani d . 1 . . C
  H3AA -0.0971 -0.3346 0.2782 0.062 Uiso calc R 1 . . H
  C4A -0.12634(11) -0.1869(5) 0.22663(19) 0.0484(11) Uani d . 1 . . C
  C5A -0.15532(11) -0.1144(5) 0.22171(19) 0.0513(11) Uani d . 1 . . C
  H5AA -0.1621 -0.0461 0.1913 0.062 Uiso calc R 1 . . H
  C6A -0.17399(10) -0.1425(4) 0.26117(19) 0.0452(10) Uani d . 1 . . C
  C7A -0.19538(10) -0.3814(5) 0.3616(2) 0.0500(11) Uani d . 1 . . C
  C8A -0.20858(12) -0.6271(5) 0.3646(2) 0.0687(15) Uani d . 1 . . C
  H8AA -0.1897 -0.6821 0.3846 0.082 Uiso calc R 1 . . H
  H8AB -0.2245 -0.6915 0.3401 0.082 Uiso calc R 1 . . H
  C9A -0.22226(13) -0.5465(5) 0.4097(2) 0.0731(15) Uani d . 1 . . C
  H9AA -0.2455 -0.5372 0.3957 0.088 Uiso calc R 1 . . H
  H9AB -0.2170 -0.5939 0.4489 0.088 Uiso calc R 1 . . H
  C10A -0.20508(11) -0.3207(6) 0.4644(2) 0.0623(13) Uani d . 1 . . C
  C11A -0.18685(11) -0.1787(5) 0.4741(2) 0.0616(13) Uani d . 1 . . C
  H11A -0.1689 -0.1839 0.4546 0.074 Uiso calc R 1 . . H
  C12A -0.20964(13) -0.0586(6) 0.4444(3) 0.0899(18) Uani d . 1 . . C
  H12A -0.1993 0.0328 0.4548 0.135 Uiso calc R 1 . . H
  H12B -0.2289 -0.0623 0.4587 0.135 Uiso calc R 1 . . H
  H12C -0.2151 -0.0706 0.4012 0.135 Uiso calc R 1 . . H
  C13A -0.17341(14) -0.1527(8) 0.5419(2) 0.105(2) Uani d . 1 . . C
  H13A -0.1618 -0.0634 0.5479 0.157 Uiso calc R 1 . . H
  H13B -0.1591 -0.2300 0.5590 0.157 Uiso calc R 1 . . H
  H13C -0.1909 -0.1483 0.5614 0.157 Uiso calc R 1 . . H
  C14A -0.10714(13) -0.1585(6) 0.1823(2) 0.0617(13) Uani d . 1 . . C
  C15A -0.05940(13) -0.2123(6) 0.1513(2) 0.0719(15) Uani d . 1 . . C
  H15A -0.0480 -0.1213 0.1592 0.086 Uiso calc R 1 . . H
  H15B -0.0726 -0.2116 0.1099 0.086 Uiso calc R 1 . . H
  C16A -0.03595(13) -0.3337(7) 0.1600(3) 0.0925(18) Uani d . 1 . . C
  H16A -0.0233 -0.3268 0.1307 0.139 Uiso calc R 1 . . H
  H16B -0.0474 -0.4234 0.1549 0.139 Uiso calc R 1 . . H
  H16C -0.0219 -0.3292 0.2002 0.139 Uiso calc R 1 . . H
  C17A -0.20408(11) -0.5192(5) 0.2654(2) 0.0571(12) Uani d . 1 . . C
  C18A -0.19824(13) -0.6677(5) 0.2408(2) 0.0676(14) Uani d . 1 . . C
  H18A -0.2020 -0.7418 0.2689 0.081 Uiso calc R 1 . . H
  C19A -0.22048(13) -0.6943(6) 0.1792(2) 0.0825(17) Uani d . 1 . . C
  H19A -0.2424 -0.6961 0.1825 0.124 Uiso calc R 1 . . H
  H19B -0.2153 -0.7850 0.1638 0.124 Uiso calc R 1 . . H
  H19C -0.2179 -0.6187 0.1520 0.124 Uiso calc R 1 . . H
  C20A -0.16294(14) -0.6740(7) 0.2380(3) 0.122(3) Uani d . 1 . . C
  H20A -0.1493 -0.6744 0.2784 0.183 Uiso calc R 1 . . H
  H20B -0.1581 -0.5915 0.2165 0.183 Uiso calc R 1 . . H
  H20C -0.1593 -0.7602 0.2173 0.183 Uiso calc R 1 . . H
  Cl1B -0.13050(3) 0.05152(13) 0.38559(6) 0.0653(4) Uani d . 1 . . Cl
  Cl2B -0.03747(3) 0.44136(12) 0.47863(6) 0.0674(4) Uani d . 1 . . Cl
  N1B -0.06767(8) 0.2099(4) 0.39475(15) 0.0458(9) Uani d . 1 . . N
  N2B -0.05164(8) -0.0332(4) 0.42627(16) 0.0453(8) Uani d . 1 . . N
  N3B -0.04767(8) 0.0474(4) 0.33506(17) 0.0515(9) Uani d . 1 . . N
  O1B -0.03938(10) 0.0643(4) 0.24268(17) 0.0935(13) Uani d . 1 . . O
  O2B -0.12900(8) 0.4901(4) 0.59723(18) 0.0900(12) Uani d . 1 . . O
  O3B -0.16752(7) 0.3361(3) 0.55356(13) 0.0589(8) Uani d . 1 . . O
  O4B -0.03881(7) 0.0823(3) 0.51723(13) 0.0585(8) Uani d . 1 . . O
  C1B -0.08434(9) 0.2460(4) 0.43712(18) 0.0393(10) Uani d . 1 . . C
  C2B -0.11430(10) 0.1861(4) 0.43739(18) 0.0414(10) Uani d . 1 . . C
  C3B -0.13224(9) 0.2340(4) 0.47628(18) 0.0443(10) Uani d . 1 . . C
  H3BA -0.1519 0.1904 0.4758 0.053 Uiso calc R 1 . . H
  C4B -0.12112(10) 0.3474(4) 0.51630(18) 0.0437(10) Uani d . 1 . . C
  C5B -0.09202(10) 0.4108(4) 0.51570(18) 0.0445(10) Uani d . 1 . . C
  H5BA -0.0844 0.4876 0.5415 0.053 Uiso calc R 1 . . H
  C6B -0.07415(9) 0.3615(4) 0.47746(18) 0.0421(10) Uani d . 1 . . C
  C7B -0.05643(9) 0.0863(5) 0.38770(19) 0.0426(10) Uani d . 1 . . C
  C8B -0.04369(12) -0.1615(5) 0.3940(2) 0.0611(13) Uani d . 1 . . C
  H8BA -0.0625 -0.2220 0.3795 0.073 Uiso calc R 1 . . H
  H8BB -0.0267 -0.2179 0.4201 0.073 Uiso calc R 1 . . H
  C9B -0.03257(11) -0.0966(5) 0.3420(2) 0.0622(13) Uani d . 1 . . C
  H9BA -0.0092 -0.0893 0.3516 0.075 Uiso calc R 1 . . H
  H9BB -0.0399 -0.1533 0.3054 0.075 Uiso calc R 1 . . H
  C10B -0.05029(11) 0.1217(6) 0.2810(2) 0.0616(13) Uani d . 1 . . C
  C11B -0.06649(12) 0.2693(6) 0.2702(2) 0.0695(14) Uani d . 1 . . C
  H11B -0.0835 0.2742 0.2923 0.083 Uiso calc R 1 . . H
  C12B -0.04069(14) 0.3822(6) 0.2964(3) 0.0915(18) Uani d . 1 . . C
  H12D -0.0331 0.3685 0.3394 0.137 Uiso calc R 1 . . H
  H12E -0.0498 0.4768 0.2883 0.137 Uiso calc R 1 . . H
  H12F -0.0230 0.3722 0.2777 0.137 Uiso calc R 1 . . H
  C13B -0.08172(15) 0.2907(8) 0.2026(2) 0.112(2) Uani d . 1 . . C
  H13D -0.0931 0.3808 0.1965 0.168 Uiso calc R 1 . . H
  H13E -0.0966 0.2137 0.1879 0.168 Uiso calc R 1 . . H
  H13F -0.0651 0.2911 0.1809 0.168 Uiso calc R 1 . . H
  C14B -0.13914(11) 0.4008(5) 0.5593(2) 0.0543(12) Uani d . 1 . . C
  C15B -0.18549(11) 0.3774(5) 0.5970(2) 0.0599(13) Uani d . 1 . . C
  H15C -0.1920 0.4774 0.5913 0.072 Uiso calc R 1 . . H
  H15D -0.1723 0.3654 0.6381 0.072 Uiso calc R 1 . . H
  C16B -0.21441(12) 0.2823(6) 0.5867(2) 0.0813(17) Uani d . 1 . . C
  H16D -0.2268 0.3061 0.6152 0.122 Uiso calc R 1 . . H
  H16E -0.2076 0.1836 0.5920 0.122 Uiso calc R 1 . . H
  H16F -0.2274 0.2961 0.5461 0.122 Uiso calc R 1 . . H
  C17B -0.04651(10) -0.0283(5) 0.4893(2) 0.0459(10) Uani d . 1 . . C
  C18B -0.05312(11) -0.1665(5) 0.5194(2) 0.0527(11) Uani d . 1 . . C
  H18B -0.0532 -0.2467 0.4914 0.063 Uiso calc R 1 . . H
  C19B -0.02783(13) -0.1945(6) 0.5772(2) 0.0840(17) Uani d . 1 . . C
  H19D -0.0314 -0.2874 0.5928 0.126 Uiso calc R 1 . . H
  H19E -0.0291 -0.1218 0.6065 0.126 Uiso calc R 1 . . H
  H19F -0.0069 -0.1923 0.5691 0.126 Uiso calc R 1 . . H
  C20B -0.08660(12) -0.1543(6) 0.5314(3) 0.0872(18) Uani d . 1 . . C
  H20D -0.1026 -0.1496 0.4934 0.131 Uiso calc R 1 . . H
  H20E -0.0877 -0.0687 0.5545 0.131 Uiso calc R 1 . . H
  H20F -0.0906 -0.2370 0.5538 0.131 Uiso calc 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
  Cl1A 0.0589(8) 0.0770(9) 0.0807(9) -0.0007(7) 0.0052(6) 0.0416(7)
  Cl2A 0.0693(8) 0.0405(7) 0.0942(9) 0.0063(6) 0.0196(7) 0.0163(7)
  N1A 0.055(2) 0.037(2) 0.058(2) -0.0116(17) 0.0143(19) 0.0056(18)
  N2A 0.059(2) 0.035(2) 0.057(2) -0.0123(17) 0.0083(18) 0.0103(18)
  N3A 0.067(3) 0.051(3) 0.062(3) -0.020(2) 0.016(2) 0.010(2)
  O1A 0.116(3) 0.081(3) 0.097(3) -0.015(2) 0.059(3) 0.008(2)
  O2A 0.096(3) 0.109(3) 0.083(3) 0.008(2) 0.033(2) 0.043(2)
  O3A 0.067(2) 0.071(2) 0.069(2) -0.0115(19) 0.0249(19) 0.0075(18)
  O4A 0.096(3) 0.0353(19) 0.066(2) -0.0120(17) -0.0037(18) 0.0104(16)
  C1A 0.054(3) 0.028(2) 0.047(3) -0.0143(19) 0.007(2) 0.0034(19)
  C2A 0.050(3) 0.037(3) 0.053(3) -0.010(2) 0.003(2) 0.009(2)
  C3A 0.049(3) 0.050(3) 0.055(3) -0.007(2) 0.008(2) 0.009(2)
  C4A 0.052(3) 0.042(3) 0.049(3) -0.011(2) 0.010(2) 0.004(2)
  C5A 0.066(3) 0.034(3) 0.051(3) -0.009(2) 0.009(2) 0.011(2)
  C6A 0.049(3) 0.026(2) 0.055(3) -0.0081(19) 0.002(2) 0.002(2)
  C7A 0.048(3) 0.046(3) 0.054(3) -0.002(2) 0.008(2) 0.013(2)
  C8A 0.080(4) 0.046(3) 0.076(4) -0.016(3) 0.012(3) 0.024(3)
  C9A 0.084(4) 0.058(3) 0.078(4) -0.028(3) 0.022(3) 0.015(3)
  C10A 0.058(3) 0.065(4) 0.068(3) -0.005(3) 0.022(3) 0.014(3)
  C11A 0.059(3) 0.069(4) 0.056(3) -0.016(3) 0.014(2) -0.003(3)
  C12A 0.084(4) 0.066(4) 0.118(5) -0.012(3) 0.021(3) -0.006(4)
  C13A 0.107(5) 0.133(6) 0.071(4) -0.027(4) 0.015(3) -0.012(4)
  C14A 0.065(4) 0.059(3) 0.059(3) -0.015(3) 0.011(3) 0.006(3)
  C15A 0.081(4) 0.075(4) 0.067(3) -0.030(3) 0.032(3) -0.009(3)
  C16A 0.080(4) 0.095(5) 0.111(5) -0.005(4) 0.040(4) 0.001(4)
  C17A 0.057(3) 0.044(3) 0.063(3) -0.015(2) 0.001(2) 0.013(3)
  C18A 0.093(4) 0.029(3) 0.076(4) -0.009(3) 0.012(3) 0.005(2)
  C19A 0.100(4) 0.065(4) 0.081(4) -0.015(3) 0.019(3) -0.012(3)
  C20A 0.086(5) 0.065(4) 0.198(8) 0.021(4) 0.004(5) -0.026(5)
  Cl1B 0.0577(7) 0.0544(8) 0.0810(9) -0.0125(6) 0.0121(6) -0.0297(6)
  Cl2B 0.0526(7) 0.0436(7) 0.1084(10) -0.0146(5) 0.0245(7) -0.0121(7)
  N1B 0.052(2) 0.033(2) 0.053(2) 0.0041(16) 0.0149(18) -0.0006(17)
  N2B 0.053(2) 0.031(2) 0.050(2) 0.0037(16) 0.0092(16) -0.0082(17)
  N3B 0.052(2) 0.049(2) 0.057(2) 0.0094(18) 0.0195(18) -0.005(2)
  O1B 0.138(4) 0.083(3) 0.077(3) 0.011(2) 0.060(3) -0.002(2)
  O2B 0.082(3) 0.093(3) 0.101(3) -0.022(2) 0.034(2) -0.054(3)
  O3B 0.056(2) 0.058(2) 0.068(2) -0.0028(16) 0.0255(16) -0.0156(17)
  O4B 0.079(2) 0.0325(18) 0.0558(19) 0.0009(15) 0.0015(16) -0.0064(15)
  C1B 0.040(2) 0.028(2) 0.046(2) 0.0034(17) 0.0045(19) 0.0032(19)
  C2B 0.045(3) 0.030(2) 0.048(3) -0.0009(18) 0.007(2) -0.0054(19)
  C3B 0.037(2) 0.038(3) 0.055(3) -0.0029(19) 0.005(2) 0.002(2)
  C4B 0.044(3) 0.036(2) 0.048(3) 0.0056(19) 0.005(2) 0.001(2)
  C5B 0.047(3) 0.026(2) 0.056(3) -0.0019(18) 0.005(2) -0.0063(19)
  C6B 0.040(2) 0.027(2) 0.057(3) -0.0035(18) 0.006(2) 0.000(2)
  C7B 0.038(2) 0.041(3) 0.049(3) -0.0009(19) 0.0097(19) -0.004(2)
  C8B 0.078(3) 0.038(3) 0.067(3) 0.006(2) 0.016(3) -0.014(2)
  C9B 0.061(3) 0.048(3) 0.080(4) 0.011(2) 0.024(3) -0.013(3)
  C10B 0.063(3) 0.071(4) 0.056(3) -0.004(3) 0.025(3) -0.003(3)
  C11B 0.072(4) 0.071(4) 0.067(4) 0.014(3) 0.022(3) 0.014(3)
  C12B 0.107(5) 0.057(4) 0.115(5) 0.002(3) 0.036(4) 0.014(4)
  C13B 0.128(6) 0.138(7) 0.068(4) 0.028(5) 0.021(4) 0.030(4)
  C14B 0.052(3) 0.046(3) 0.063(3) 0.001(2) 0.009(2) -0.012(2)
  C15B 0.064(3) 0.064(3) 0.057(3) 0.006(3) 0.026(2) -0.003(3)
  C16B 0.073(4) 0.090(4) 0.089(4) -0.019(3) 0.036(3) -0.013(3)
  C17B 0.049(3) 0.036(3) 0.052(3) 0.007(2) 0.009(2) -0.002(2)
  C18B 0.068(3) 0.031(2) 0.057(3) 0.007(2) 0.010(2) -0.004(2)
  C19B 0.079(4) 0.071(4) 0.095(4) 0.004(3) 0.010(3) 0.027(3)
  C20B 0.069(4) 0.068(4) 0.123(5) -0.002(3) 0.020(3) 0.025(4)
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
  Cl1A C2A . 1.732(4) ?
  Cl2A C6A . 1.733(4) ?
  N1A C7A . 1.282(5) yes
  N1A C1A . 1.381(5) yes
  N2A C17A . 1.382(6) yes
  N2A C7A . 1.411(6) yes
  N2A C8A . 1.477(5) yes
  N3A C7A . 1.378(5) yes
  N3A C10A . 1.395(6) yes
  N3A C9A . 1.481(6) yes
  O1A C10A . 1.206(5) yes
  O2A C14A . 1.206(5) yes
  O3A C14A . 1.331(6) yes
  O3A C15A . 1.456(5) yes
  O4A C17A . 1.209(5) yes
  C1A C6A . 1.407(5) ?
  C1A C2A . 1.407(6) ?
  C2A C3A . 1.374(6) ?
  C3A C4A . 1.396(6) ?
  C4A C5A . 1.391(6) ?
  C4A C14A . 1.474(6) ?
  C5A C6A . 1.367(6) ?
  C8A C9A . 1.502(7) ?
  C10A C11A . 1.520(7) ?
  C11A C12A . 1.525(7) ?
  C11A C13A . 1.525(6) ?
  C15A C16A . 1.490(7) ?
  C17A C18A . 1.533(7) ?
  C18A C19A . 1.506(6) ?
  C18A C20A . 1.528(7) ?
  Cl1B C2B . 1.739(4) ?
  Cl2B C6B . 1.729(4) ?
  N1B C7B . 1.270(5) yes
  N1B C1B . 1.376(5) yes
  N2B C17B . 1.397(5) yes
  N2B C7B . 1.398(5) yes
  N2B C8B . 1.482(5) yes
  N3B C7B . 1.389(5) yes
  N3B C10B . 1.391(6) yes
  N3B C9B . 1.476(5) yes
  O1B C10B . 1.209(5) yes
  O2B C14B . 1.198(5) yes
  O3B C14B . 1.332(5) yes
  O3B C15B . 1.447(5) yes
  O4B C17B . 1.209(5) yes
  C1B C2B . 1.399(5) ?
  C1B C6B . 1.409(5) ?
  C2B C3B . 1.381(5) ?
  C3B C4B . 1.397(5) ?
  C4B C5B . 1.380(5) ?
  C4B C14B . 1.473(6) ?
  C5B C6B . 1.372(5) ?
  C8B C9B . 1.506(6) ?
  C10B C11B . 1.529(7) ?
  C11B C13B . 1.527(6) ?
  C11B C12B . 1.532(7) ?
  C15B C16B . 1.490(6) ?
  C17B C18B . 1.514(6) ?
  C18B C19B . 1.502(6) ?
  C18B C20B . 1.527(6) ?