data_2008842
_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  'C22 H29 Cl2 N3 O4'
_chemical_formula_weight  470.38
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y+1/2, z+1/2'
_cell_length_a  12.02440(10)
_cell_length_b  21.81280(10)
_cell_length_c  9.56630(10)
_cell_angle_alpha  90.00
_cell_angle_beta  101.4030(10)
_cell_angle_gamma  90.00
_cell_volume  2459.58(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.270
_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 0.36051(8) 0.63521(4) 0.70223(12) 0.0696(3) Uani d . 1 . . Cl
  Cl2 0.24738(8) 0.45672(4) 0.30976(10) 0.0653(3) Uani d . 1 . . Cl
  O1 -0.0013(2) 0.71756(12) 0.2509(3) 0.0740(8) Uani d . 1 . . O
  O2 0.12003(17) 0.48158(9) 0.5930(2) 0.0438(5) Uani d . 1 . . O
  O3 0.4899(3) 0.36473(17) 0.8080(5) 0.1099(13) Uani d . 1 . . O
  O4 0.4134(4) 0.4142(2) 0.9643(5) 0.1282(15) Uani d . 1 . . O
  N1 0.2207(2) 0.57875(11) 0.4357(3) 0.0441(6) Uani d . 1 . . N
  N2 0.0964(2) 0.58480(10) 0.6046(3) 0.0407(6) Uani d . 1 . . N
  N3 0.0686(2) 0.64860(10) 0.4155(3) 0.0437(6) Uani d . 1 . . N
  C1 0.3009(2) 0.54080(13) 0.5200(3) 0.0417(7) Uani d . 1 . . C
  C2 0.3702(3) 0.55978(14) 0.6457(4) 0.0469(7) Uani d . 1 . . C
  C3 0.4479(3) 0.52195(17) 0.7287(4) 0.0538(8) Uani d . 1 . . C
  H3 0.4909 0.5362 0.8140 0.065 Uiso calc R 1 . . H
  C4 0.4617(3) 0.46283(16) 0.6848(4) 0.0559(9) Uani d . 1 . . C
  C5 0.4006(3) 0.44339(15) 0.5554(4) 0.0553(9) Uani d . 1 . . C
  H5 0.4121 0.4042 0.5226 0.066 Uiso calc R 1 . . H
  C6 0.3221(3) 0.48184(14) 0.4738(3) 0.0455(7) Uani d . 1 . . C
  C7 0.1370(2) 0.60020(12) 0.4820(3) 0.0370(6) Uani d . 1 . . C
  C8 0.0171(3) 0.63274(14) 0.6345(4) 0.0494(8) Uani d . 1 . . C
  H8B 0.0560 0.6632 0.7003 0.059 Uiso calc R 1 . . H
  H8A -0.0444 0.6152 0.6734 0.059 Uiso calc R 1 . . H
  C9 -0.0254(3) 0.65962(14) 0.4900(4) 0.0503(8) Uani d . 1 . . C
  H9B -0.0940 0.6392 0.4420 0.060 Uiso calc R 1 . . H
  H9A -0.0404 0.7031 0.4962 0.060 Uiso calc R 1 . . H
  C10 0.0735(3) 0.68145(14) 0.2919(4) 0.0521(8) Uani d . 1 . . C
  C11 0.1731(4) 0.67321(16) 0.2197(4) 0.0641(10) Uani d . 1 . . C
  H11 0.1956 0.6300 0.2257 0.077 Uiso calc R 1 . . H
  C12 0.1413(6) 0.6916(3) 0.0633(6) 0.123(2) Uani d . 1 . . C
  H12C 0.1975 0.6765 0.0134 0.184 Uiso calc R 1 . . H
  H12B 0.1375 0.7354 0.0560 0.184 Uiso calc R 1 . . H
  H12A 0.0687 0.6744 0.0220 0.184 Uiso calc R 1 . . H
  C13 0.2708(4) 0.71151(19) 0.2981(6) 0.0912(16) Uani d . 1 . . C
  H13C 0.3326 0.7098 0.2482 0.137 Uiso calc R 1 . . H
  H13B 0.2952 0.6958 0.3929 0.137 Uiso calc R 1 . . H
  H13A 0.2466 0.7533 0.3028 0.137 Uiso calc R 1 . . H
  C14 0.0996(2) 0.52497(13) 0.6605(3) 0.0391(7) Uani d . 1 . . C
  C15 0.0855(3) 0.52041(15) 0.8146(3) 0.0475(7) Uani d . 1 . . C
  H15 0.0283 0.5502 0.8305 0.057 Uiso calc R 1 . . H
  C16 0.0465(4) 0.45677(17) 0.8464(4) 0.0734(12) Uani d . 1 . . C
  H16C 0.0438 0.4538 0.9458 0.110 Uiso calc R 1 . . H
  H16B 0.0988 0.4269 0.8234 0.110 Uiso calc R 1 . . H
  H16A -0.0276 0.4493 0.7901 0.110 Uiso calc R 1 . . H
  C17 0.1985(4) 0.5362(2) 0.9118(4) 0.0790(13) Uani d . 1 . . C
  H17C 0.2218 0.5765 0.8892 0.118 Uiso calc R 1 . . H
  H17B 0.2549 0.5069 0.8979 0.118 Uiso calc R 1 . . H
  H17A 0.1900 0.5352 1.0094 0.118 Uiso calc R 1 . . H
  C18 0.5442(3) 0.4203(2) 0.7752(5) 0.0802(13) Uani d . 1 . . C
  H18B 0.6045 0.4102 0.7252 0.096 Uiso calc R 1 . . H
  H18A 0.5779 0.4409 0.8632 0.096 Uiso calc R 1 . . H
  C19 0.4278(5) 0.3675(3) 0.8997(6) 0.0966(16) Uani d . 1 . . C
  C20 0.3677(8) 0.3088(3) 0.9271(9) 0.145(3) Uani d D 1 . . C
  H20 0.3172 0.3020 0.8346 0.174 Uiso calc R 1 . . H
  C21 0.4311(12) 0.2518(5) 0.9466(14) 0.284(8) Uani d D 1 . . C
  H21C 0.4763 0.2483 0.8747 0.426 Uiso calc R 1 . . H
  H21B 0.3793 0.2179 0.9387 0.426 Uiso calc R 1 . . H
  H21A 0.4796 0.2515 1.0392 0.426 Uiso calc R 1 . . H
  C22 0.2847(9) 0.3202(5) 1.0218(13) 0.229(5) Uani d . 1 . . C
  H22C 0.2122 0.3306 0.9646 0.343 Uiso calc R 1 . . H
  H22B 0.3111 0.3535 1.0854 0.343 Uiso calc R 1 . . H
  H22A 0.2775 0.2840 1.0761 0.343 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
  Cl1 0.0637(6) 0.0547(5) 0.0872(8) -0.0053(4) 0.0070(5) -0.0154(4)
  Cl2 0.0633(6) 0.0720(6) 0.0600(6) 0.0034(4) 0.0105(5) -0.0137(4)
  O1 0.0764(18) 0.0672(16) 0.0774(19) 0.0264(14) 0.0127(15) 0.0228(14)
  O2 0.0455(12) 0.0409(11) 0.0466(13) -0.0004(9) 0.0132(10) -0.0019(9)
  O3 0.101(3) 0.116(3) 0.116(3) 0.043(2) 0.030(2) 0.051(2)
  O4 0.154(4) 0.132(4) 0.097(3) 0.007(3) 0.021(3) -0.005(2)
  N1 0.0450(14) 0.0456(14) 0.0435(15) 0.0057(11) 0.0133(12) 0.0079(11)
  N2 0.0382(13) 0.0434(14) 0.0420(15) 0.0018(10) 0.0114(11) -0.0007(10)
  N3 0.0443(14) 0.0389(13) 0.0481(16) 0.0079(10) 0.0100(12) 0.0033(11)
  C1 0.0349(15) 0.0468(16) 0.0458(18) 0.0054(12) 0.0136(14) 0.0113(13)
  C2 0.0357(15) 0.0477(17) 0.058(2) -0.0014(12) 0.0117(15) 0.0019(14)
  C3 0.0342(16) 0.072(2) 0.054(2) -0.0018(15) 0.0060(15) 0.0060(16)
  C4 0.0347(16) 0.068(2) 0.064(2) 0.0070(14) 0.0081(17) 0.0179(17)
  C5 0.0457(18) 0.0478(18) 0.078(3) 0.0100(14) 0.0254(19) 0.0078(16)
  C6 0.0400(16) 0.0515(17) 0.0477(19) 0.0018(13) 0.0152(15) 0.0038(14)
  C7 0.0360(15) 0.0353(14) 0.0397(17) -0.0008(11) 0.0072(13) 0.0010(11)
  C8 0.0515(18) 0.0450(17) 0.055(2) 0.0083(13) 0.0201(17) -0.0020(14)
  C9 0.0443(17) 0.0439(17) 0.064(2) 0.0086(13) 0.0136(16) 0.0006(15)
  C10 0.064(2) 0.0392(16) 0.052(2) 0.0086(15) 0.0105(17) 0.0043(14)
  C11 0.090(3) 0.0481(19) 0.061(2) 0.0185(18) 0.031(2) 0.0144(16)
  C12 0.184(6) 0.118(4) 0.081(4) 0.076(4) 0.065(4) 0.053(3)
  C13 0.086(3) 0.064(3) 0.139(5) -0.006(2) 0.060(3) 0.002(3)
  C14 0.0308(14) 0.0441(16) 0.0409(17) -0.0001(11) 0.0035(13) 0.0019(12)
  C15 0.0480(18) 0.0568(18) 0.0388(17) 0.0006(14) 0.0113(15) 0.0016(13)
  C16 0.102(3) 0.070(2) 0.053(2) -0.015(2) 0.028(2) 0.0095(18)
  C17 0.070(3) 0.126(4) 0.037(2) -0.015(2) 0.0002(19) -0.004(2)
  C18 0.054(2) 0.089(3) 0.096(3) 0.018(2) 0.011(2) 0.038(2)
  C19 0.099(4) 0.112(4) 0.072(3) 0.019(3) 0.000(3) 0.018(3)
  C20 0.182(7) 0.107(5) 0.168(7) 0.003(5) 0.084(6) 0.040(4)
  C21 0.38(2) 0.147(8) 0.375(19) 0.090(10) 0.196(17) 0.088(10)
  C22 0.161(9) 0.237(12) 0.313(15) 0.017(7) 0.107(10) 0.060(11)
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 . 1.743(3) ?
  Cl2 C6 . 1.736(4) ?
  O1 C10 . 1.201(4) yes
  O2 C14 . 1.198(3) yes
  O3 C19 . 1.261(7) yes
  O3 C18 . 1.441(5) yes
  O4 C19 . 1.222(6) yes
  N1 C7 . 1.266(3) yes
  N1 C1 . 1.400(4) yes
  N2 C7 . 1.398(4) yes
  N2 C14 . 1.408(4) yes
  N2 C8 . 1.481(4) yes
  N3 C10 . 1.394(4) yes
  N3 C7 . 1.410(4) yes
  N3 C9 . 1.470(4) yes
  C1 C2 . 1.384(5) ?
  C1 C6 . 1.400(4) ?
  C2 C3 . 1.375(5) ?
  C3 C4 . 1.376(5) ?
  C4 C5 . 1.376(5) ?
  C4 C18 . 1.500(5) ?
  C5 C6 . 1.383(5) ?
  C8 C9 . 1.496(5) ?
  C10 C11 . 1.507(5) ?
  C11 C13 . 1.514(6) ?
  C11 C12 . 1.522(6) ?
  C14 C15 . 1.520(4) ?
  C15 C16 . 1.515(5) ?
  C15 C17 . 1.527(5) ?
  C19 C20 . 1.518(9) ?
  C20 C21 . 1.451(8) ?
  C20 C22 . 1.495(10) ?