data_2008841
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_publ_section_title
;
Substituted clonidine derivatives. III.
3,5-Dichloro-4-(imidazolidin-2-ylideneamino)benzyl alcohol and
3,5-dichloro-4-(1,3-diisobutyrylimidazolidin-2-ylideneamino)benzyl
isobutyrate
;
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  'C10 H11 Cl2 N3 O'
_chemical_formula_weight  260.12
_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  13.73000(10)
_cell_length_b  8.54000(10)
_cell_length_c  19.74100(10)
_cell_angle_alpha  90.00
_cell_angle_beta  96.3630(10)
_cell_angle_gamma  90.00
_cell_volume  2300.41(3)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.502
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.036
_refine_ls_wR_factor_obs  0.085
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  Cl1A 0.42392(5) 0.36544(7) 0.03923(3) 0.0680(2) Uani d . 1 . Cl
  Cl2A 0.73994(5) -0.01344(11) 0.07353(4) 0.0809(2) Uani d . 1 . Cl
  O1A 0.56776(14) -0.0588(2) -0.18155(8) 0.0624(5) Uani d . 1 . O
  N1A 0.58465(14) 0.1908(2) 0.12355(8) 0.0511(4) Uani d . 1 . N
  N2A 0.6797(2) 0.4240(2) 0.12698(9) 0.0568(5) Uani d . 1 . N
  N3A 0.63826(15) 0.3287(2) 0.22268(8) 0.0534(5) Uani d . 1 . N
  C1A 0.58283(14) 0.1784(2) 0.05227(9) 0.0396(4) Uani d . 1 . C
  C2A 0.51072(15) 0.2480(2) 0.00722(10) 0.0419(4) Uani d . 1 . C
  C3A 0.5041(2) 0.2265(2) -0.06273(10) 0.0428(4) Uani d . 1 . C
  C4A 0.57073(15) 0.1318(2) -0.09058(9) 0.0399(4) Uani d . 1 . C
  C5A 0.64336(15) 0.0603(2) -0.04749(10) 0.0432(4) Uani d . 1 . C
  C6A 0.64846(14) 0.0831(2) 0.02191(10) 0.0424(4) Uani d . 1 . C
  C7A 0.63108(14) 0.3058(2) 0.15433(9) 0.0406(4) Uani d . 1 . C
  C8A 0.7314(2) 0.5222(4) 0.17898(12) 0.0663(7) Uani d . 1 . C
  C9A 0.6806(3) 0.4784(4) 0.24084(13) 0.0750(9) Uani d . 1 . C
  C10A 0.5633(2) 0.1024(3) -0.16645(11) 0.0557(6) Uani d . 1 . C
  Cl1B 0.22181(3) 0.60419(5) 0.03186(2) 0.03881(11) Uani d . 1 . Cl
  Cl2B -0.03955(4) 0.24597(6) 0.14581(2) 0.04613(13) Uani d . 1 . Cl
  O1B 0.02671(11) 0.2832(2) -0.16611(6) 0.0462(3) Uani d . 1 . O
  N1B 0.11442(10) 0.4885(2) 0.14805(7) 0.0316(3) Uani d . 1 . N
  N2B 0.28017(11) 0.3968(2) 0.17022(8) 0.0364(3) Uani d . 1 . N
  N3B 0.22575(12) 0.5778(2) 0.23643(8) 0.0419(4) Uani d . 1 . N
  C1B 0.09686(11) 0.4077(2) 0.08637(8) 0.0283(3) Uani d . 1 . C
  C2B 0.13901(11) 0.4488(2) 0.02754(8) 0.0301(3) Uani d . 1 . C
  C3B 0.11324(13) 0.3781(2) -0.03501(8) 0.0343(4) Uani d . 1 . C
  C4B 0.04248(13) 0.2622(2) -0.04164(8) 0.0334(4) Uani d . 1 . C
  C5B -0.00211(13) 0.2192(2) 0.01528(9) 0.0341(4) Uani d . 1 . C
  C6B 0.02458(12) 0.2919(2) 0.07717(8) 0.0309(3) Uani d . 1 . C
  C7B 0.20124(12) 0.4863(2) 0.18107(8) 0.0292(3) Uani d . 1 . C
  C8B 0.36639(15) 0.4501(3) 0.21386(12) 0.0495(5) Uani d . 1 . C
  C9B 0.3193(2) 0.5260(4) 0.27145(12) 0.0567(6) Uani d . 1 . C
  C10B 0.0115(2) 0.1874(3) -0.11015(10) 0.0462(5) Uani d . 1 . C
  H1O1 0.521(2)  -0.104(4)  -0.1633(15) 0.083(9) Uiso d . 1 . H
  H1N2 0.6914(17) 0.416(3)  0.0903(13) 0.055(7) Uiso d . 1 . H
  H1N3 0.6011(16) 0.281(3)  0.2465(11) 0.045(6) Uiso d . 1 . H
  H3A 0.4537(18) 0.274(3)  -0.0905(13) 0.062(7) Uiso d . 1 . H
  H5A 0.6894(18) -0.006(3)  -0.0647(12) 0.060(7) Uiso d . 1 . H
  H8A 0.799(3)  0.489(4)  0.1880(16) 0.095(11) Uiso d . 1 . H
  H8B 0.723(2)  0.637(4)  0.1667(16) 0.097(11) Uiso d . 1 . H
  H9A 0.721(2)  0.478(4)  0.2790(17) 0.088(10) Uiso d . 1 . H
  H9B 0.618(3)  0.561(5)  0.2469(19) 0.131(14) Uiso d . 1 . H
  H10A 0.501(2)  0.147(3)  -0.1867(14) 0.078(9) Uiso d . 1 . H
  H10B 0.6188(19) 0.155(3)  -0.1859(13) 0.068(7) Uiso d . 1 . H
  H2O2 -0.015(2)  0.353(3)  -0.1696(14) 0.074(9) Uiso d . 1 . H
  H2N2 0.2843(15) 0.358(3)  0.1309(12) 0.046(6) Uiso d . 1 . H
  H2N3 0.1799(17) 0.600(3)  0.2591(12) 0.048(6) Uiso d . 1 . H
  H3B 0.1439(14) 0.411(2)  -0.0733(10) 0.038(5) Uiso d . 1 . H
  H5B -0.0540(15) 0.144(3)  0.0123(10) 0.040(5) Uiso d . 1 . H
  H8C 0.4086(17) 0.365(3)  0.2280(12) 0.058(7) Uiso d . 1 . H
  H8D 0.4034(17) 0.528(3)  0.1899(11) 0.053(6) Uiso d . 1 . H
  H9C 0.3052(19) 0.448(3)  0.3074(14) 0.072(8) Uiso d . 1 . H
  H9D 0.357(2)  0.616(3)  0.2902(14) 0.075(8) Uiso d . 1 . H
  H10C -0.0567(18) 0.162(3)  -0.1116(12) 0.056(7) Uiso d . 1 . H
  H10D 0.0486(18) 0.088(3)  -0.1146(12) 0.062(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
  Cl1A 0.0854(4) 0.0568(3) 0.0705(4) 0.0191(3) 0.0469(3) 0.0042(3)
  Cl2A 0.0583(4) 0.1162(6) 0.0649(4) 0.0187(4) -0.0082(3) 0.0045(4)
  O1A 0.0900(12) 0.0554(9) 0.0489(8) -0.0296(9) 0.0394(9) -0.0207(7)
  N1A 0.0690(11) 0.0537(10) 0.0332(8) -0.0231(9) 0.0178(8) -0.0056(7)
  N2A 0.0772(13) 0.0654(12) 0.0310(8) -0.0348(10) 0.0201(9) -0.0134(8)
  N3A 0.0645(11) 0.0696(13) 0.0281(8) -0.0155(10) 0.0136(8) -0.0037(8)
  C1A 0.0478(10) 0.0393(10) 0.0340(9) -0.0162(8) 0.0144(8) -0.0049(7)
  C2A 0.0515(11) 0.0346(9) 0.0433(10) -0.0023(8) 0.0222(8) -0.0028(8)
  C3A 0.0518(11) 0.0399(10) 0.0382(10) 0.0003(9) 0.0113(8) 0.0053(8)
  C4A 0.0528(11) 0.0342(9) 0.0349(9) -0.0109(8) 0.0141(8) -0.0043(7)
  C5A 0.0465(10) 0.0413(11) 0.0446(10) -0.0032(8) 0.0170(8) -0.0086(8)
  C6A 0.0381(9) 0.0467(11) 0.0428(10) -0.0063(8) 0.0062(8) -0.0017(8)
  C7A 0.0444(10) 0.0503(11) 0.0287(8) -0.0059(9) 0.0115(7) -0.0025(8)
  C8A 0.078(2) 0.080(2) 0.0431(12) -0.034(2) 0.0136(11) -0.0200(12)
  C9A 0.095(2) 0.094(2) 0.0379(12) -0.036(2) 0.0178(13) -0.0226(13)
  C10A 0.083(2) 0.0522(13) 0.0352(10) -0.0120(12) 0.0196(11) -0.0055(9)
  Cl1B 0.0383(2) 0.0418(2) 0.0369(2) -0.0090(2) 0.0067(2) 0.0004(2)
  Cl2B 0.0497(3) 0.0503(3) 0.0408(2) -0.0083(2) 0.0159(2) 0.0036(2)
  O1B 0.0540(8) 0.0569(9) 0.0271(6) 0.0174(7) 0.0024(5) -0.0072(6)
  N1B 0.0317(7) 0.0380(8) 0.0251(6) 0.0030(6) 0.0039(5) -0.0062(6)
  N2B 0.0349(7) 0.0418(9) 0.0320(8) 0.0066(6) 0.0017(6) -0.0030(6)
  N3B 0.0402(9) 0.0515(10) 0.0329(8) 0.0034(7) -0.0014(7) -0.0124(7)
  C1B 0.0280(7) 0.0304(8) 0.0263(7) 0.0039(6) 0.0016(6) -0.0025(6)
  C2B 0.0288(8) 0.0317(8) 0.0298(8) 0.0003(6) 0.0030(6) -0.0011(6)
  C3B 0.0382(9) 0.0393(9) 0.0256(8) 0.0034(7) 0.0049(7) -0.0006(7)
  C4B 0.0387(9) 0.0321(9) 0.0279(8) 0.0061(7) -0.0035(6) -0.0054(7)
  C5B 0.0350(8) 0.0289(9) 0.0371(9) -0.0001(7) -0.0022(7) -0.0012(7)
  C6B 0.0326(8) 0.0314(8) 0.0290(8) 0.0031(7) 0.0053(6) 0.0027(6)
  C7B 0.0348(8) 0.0287(8) 0.0247(7) 0.0001(6) 0.0052(6) 0.0002(6)
  C8B 0.0351(10) 0.0551(13) 0.0564(12) 0.0041(9) -0.0027(9) 0.0004(10)
  C9B 0.0475(12) 0.076(2) 0.0429(12) 0.0021(11) -0.0122(9) -0.0109(11)
  C10B 0.0581(13) 0.0449(11) 0.0334(9) 0.0017(10) -0.0050(8) -0.0099(8)
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 . 1.730(2) ?
  Cl2A C6A . 1.735(2) ?
  O1A C10A . 1.411(3) yes
  O1A H1O1 . 0.87(3) ?
  N1A C7A . 1.286(3) yes
  N1A C1A . 1.408(2) yes
  N2A C7A . 1.355(3) yes
  N2A C8A . 1.449(3) yes
  N2A H1N2 . 0.76(2) ?
  N3A C7A . 1.356(2) yes
  N3A C9A . 1.433(3) yes
  N3A H1N3 . 0.84(2) ?
  C1A C2A . 1.389(3) ?
  C1A C6A . 1.398(3) ?
  C2A C3A . 1.386(3) ?
  C3A C4A . 1.381(3) ?
  C3A H3A . 0.93(3) ?
  C4A C5A . 1.379(3) ?
  C4A C10A . 1.511(3) ?
  C5A C6A . 1.378(3) ?
  C5A H5A . 0.94(2) ?
  C8A C9A . 1.518(3) ?
  C8A H8A . 0.97(3) ?
  C8A H8B . 1.01(3) ?
  C9A H9A . 0.88(3) ?
  C9A H9B . 1.13(4) ?
  C10A H10A . 0.99(3) ?
  C10A H10B . 1.00(3) ?
  Cl1B C2B . 1.744(2) ?
  Cl2B C6B . 1.741(2) ?
  O1B C10B . 1.409(3) yes
  O1B H2O2 . 0.82(3) ?
  N1B C7B . 1.294(2) yes
  N1B C1B . 1.397(2) yes
  N2B C7B . 1.362(2) yes
  N2B C8B . 1.458(3) yes
  N2B H2N2 . 0.85(2) ?
  N3B C7B . 1.356(2) yes
  N3B C9B . 1.458(3) yes
  N3B H2N3 . 0.83(2) ?
  C1B C2B . 1.398(2) ?
  C1B C6B . 1.399(2) ?
  C2B C3B . 1.385(2) ?
  C3B C4B . 1.383(3) ?
  C3B H3B . 0.95(2) ?
  C4B C5B . 1.387(3) ?
  C4B C10B . 1.514(2) ?
  C5B C6B . 1.383(2) ?
  C5B H5B . 0.96(2) ?
  C8B C9B . 1.514(3) ?
  C8B H8C . 0.95(2) ?
  C8B H8D . 0.99(2) ?
  C9B H9C . 1.01(3) ?
  C9B H9D . 0.97(3) ?
  C10B H10C . 0.96(2) ?
  C10B H10D . 1.00(3) ?