#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2010497.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_2010497
_journal_name_full  'Acta Crystallographica'
_journal_year  1995
_journal_volume  C51
_journal_page_first  277
_journal_page_last  279
_publ_section_title
;
(E,E)-4-[3-(3,5-Dichloro-2-hydroxyphenylazo)-2-morpholino-2-butenoyl]morpholine
;
loop_
_publ_author_name
  'Ramm, Matthias'
  'Baumann, Hendrik'
  'Kirschke, Klaus'
_chemical_formula_moiety  'C18 H22 Cl2 N4 O4'
_chemical_formula_sum  'C18 H22 Cl2 N4 O4'
_chemical_formula_weight  429.30
_chemical_melting_point  '75 -78_C'
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  'X,Y,Z'
  '1/2+X,1/2-Y,1/2+Z'
  '-X,-Y,-Z'
  '1/2-X,1/2+Y,1/2-Z'
_cell_length_a  14.9821(9)
_cell_length_b  5.9131(7)
_cell_length_c  23.502(2)
_cell_angle_alpha  90
_cell_angle_beta  105.990(10)
_cell_angle_gamma  90
_cell_volume  2001.6(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.424
_diffrn_ambient_temperature  298
_refine_ls_R_factor_obs  0.037
_refine_ls_wR_factor_obs  0.059
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
  Cl1 0.26296(4) 0.9411(2) 0.05295(3) 0.0829(2) Uani
  Cl2 0.31115(5) 0.3363(2) 0.23047(4) 0.0866(3) Uani
  O1 0.68630(10)
  0.5948(3) 0.39136(7) 0.0505(4) Uani
  O2 0.41860(10)
  0.9824(3) 0.41760(7) 0.0576(5) Uani
  O3 0.97980(10)
  0.8448(3) 0.44071(7) 0.0643(6) Uani
  O4 0.48390(10)
  0.5773(3) 0.28123(7) 0.0635(5) Uani
  N1 0.59990(10)
  0.8746(3) 0.41505(7) 0.0396(5) Uani
  N2 0.79930(10)
  1.0310(3) 0.39646(7) 0.0450(5) Uani
  N3 0.59220(10)
  0.9185(3) 0.28033(7) 0.0432(5) Uani
  N4 0.54760(10)
  0.9788(3) 0.22727(7) 0.0490(5) Uani
  C1 0.71470(10)
  0.9672(4) 0.36269(8) 0.0390(5) Uani
  C2 0.66480(10)
  0.7943(3) 0.39071(8) 0.0370(5) Uani
  C3 0.5705(2) 1.1098(4) 0.41480(10)
  0.0494(6) Uani
  C4 0.4669(2) 1.1214(4) 0.38650(10)
  0.0603(8) Uani
  C5 0.44530(10)
  0.7528(4) 0.41490(10)
  0.0535(7) Uani
  C6 0.54790(10)
  0.7239(4) 0.44340(10)
  0.0468(6) Uani
  C7 0.83560(10)
  0.9630(5) 0.45868(9) 0.0534(7) Uani
  C8 0.9054(2) 0.7772(5) 0.46400(10)
  0.0623(8) Uani
  C9 0.9454(2) 0.9113(5) 0.38080(10)
  0.0606(8) Uani
  C10 0.87580(10)
  1.0997(5) 0.37200(10)
  0.0558(7) Uani
  C11 0.67070(10)
  1.0422(4) 0.30629(8) 0.0417(6) Uani
  C12 0.6948(2) 1.2464(4) 0.27650(10)
  0.0508(6) Uani
  C13 0.46550(10)
  0.8544(4) 0.20287(9) 0.0484(6) Uani
  C14 0.4127(2) 0.9342(5) 0.14820(10)
  0.0557(7) Uani
  C15 0.32970(10)
  0.8308(5) 0.12040(10)
  0.0602(7) Uani
  C16 0.2982(2) 0.6459(5) 0.14490(10)
  0.0653(8) Uani
  C17 0.3507(2) 0.5656(5) 0.19860(10)
  0.0599(7) Uani
  C18 0.43500(10)
  0.6655(4) 0.22900(10)
  0.0522(6) Uani
  H4O 0.526(2) 0.680(6) 0.2940(10)
  0.24(2) Uiso
  H14 0.4340(10)
  1.064(4) 0.1302(9) 0.110(10)
  Uiso
  H16 0.243(2) 0.586(4) 0.1240(10)
  0.14(2) Uiso
  H31 0.603(2) 1.197(4) 0.3960(10)
  0.120(10)
  Uiso
  H32 0.583(2) 1.156(4) 0.4600(10)
  0.120(10)
  Uiso
  H41 0.444(2) 1.275(4) 0.3900(10)
  0.130(10)
  Uiso
  H42 0.454(2) 1.069(4) 0.3440(10)
  0.15(2) Uiso
  H51 0.410(2) 0.664(4) 0.4380(10)
  0.120(10)
  Uiso
  H52 0.430(2) 0.704(4) 0.3738(9) 0.110(10)
  Uiso
  H61 0.567(2) 0.569(4) 0.4390(10)
  0.120(10)
  Uiso
  H62 0.561(2) 0.761(4) 0.4880(10)
  0.120(10)
  Uiso
  H71 0.784(2) 0.928(4) 0.4744(9) 0.120(10)
  Uiso
  H72 0.865(2) 1.102(4) 0.4810(10)
  0.120(10)
  Uiso
  H81 0.876(2) 0.643(5) 0.4470(10)
  0.16(2) Uiso
  H82 0.927(2) 0.740(4) 0.5060(10)
  0.14(2) Uiso
  H91 1.001(2) 0.952(5) 0.3660(10)
  0.16(2) Uiso
  H92 0.913(2) 0.775(4) 0.3580(10)
  0.15(2) Uiso
  H101 0.905(2) 1.240(5) 0.3920(10)
  0.15(2) Uiso
  H102 0.854(2) 1.133(4) 0.3300(10)
  0.120(10)
  Uiso
  H121 0.738(2) 1.342(4) 0.3060(10)
  0.14(2) Uiso
  H122 0.728(2) 1.220(4) 0.2470(10)
  0.130(10)
  Uiso
  H123 0.632(2) 1.331(4) 0.2560(10)
  0.14(2) Uiso
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 0.0505(3) 0.1230(6) 0.0607(3) -0.0207(4) -0.0091(3) 0.0131(4)
  Cl2 0.0696(3) 0.0880(5) 0.1042(5) -0.0155(4) 0.0272(3) -0.0301(3)
  O1 0.0496(7) 0.0396(8) 0.0654(8) -0.0034(7) 0.0212(6) 0.0049(6)
  O2 0.0423(6) 0.0559(9) 0.0774(9) -0.0025(8) 0.0213(6) 0.0075(7)
  O3 0.0390(7) 0.0940(10)
  0.0544(8) -0.0009(9) 0.0044(6) 0.0019(8)
  O4 0.0584(8) 0.0720(10)
  0.0564(8) -0.0033(8) 0.0094(7) -0.0153(8)
  N1 0.0377(7) 0.0340(9) 0.0506(8) 0.0017(7) 0.0179(6) 0.0008(6)
  N2 0.0334(7) 0.0580(10)
  0.0417(8) -0.0002(8) 0.0077(6) -0.0078(8)
  N3 0.0362(7) 0.0540(10)
  0.0377(7) -0.0052(8) 0.0076(6) -0.0030(8)
  N4 0.0395(8) 0.0640(10)
  0.0402(8) -0.0059(9) 0.0061(6) -0.0051(8)
  C1 0.0332(7) 0.0450(10)
  0.0395(8) -0.0053(9) 0.0108(6) -0.0030(8)
  C2 0.0314(7) 0.0390(10)
  0.0383(9) -0.0026(9) 0.0056(6) -0.0002(8)
  C3 0.0530(10)
  0.0340(10)
  0.0670(10)
  -0.0010(10)
  0.0265(8) 0.0003(9)
  C4 0.0560(10)
  0.0450(10)
  0.080(2) 0.0050(10)
  0.0200(10)
  0.0130(10)
  C5 0.0449(9) 0.0540(10)
  0.0670(10)
  -0.0030(10)
  0.0237(8) -0.0050(10)
  C6 0.0461(9) 0.0410(10)
  0.0580(10)
  0.0070(10)
  0.0228(7) 0.0023(9)
  C7 0.0407(9) 0.077(2) 0.0400(10)
  -0.0060(10)
  0.0073(8) -0.0100(10)
  C8 0.0480(10)
  0.082(2) 0.0510(10)
  0.0090(10)
  0.0030(10)
  -0.0030(10)
  C9 0.0421(9) 0.087(2) 0.0540(10)
  -0.0030(10)
  0.0154(8) -0.0020(10)
  C10 0.0380(9) 0.070(2) 0.0600(10)
  0.0060(10)
  0.0140(8) -0.0100(10)
  C11 0.0356(8) 0.0510(10)
  0.0377(9) -0.0040(9) 0.0089(7) -0.0034(9)
  C12 0.0480(10)
  0.0570(10)
  0.0450(10)
  0.0030(10)
  0.0091(8) -0.0040(10)
  C13 0.0356(8) 0.0640(10)
  0.0430(10)
  -0.0130(10)
  0.0075(7) -0.0040(10)
  C14 0.0408(9) 0.076(2) 0.0470(10)
  -0.0130(10)
  0.0069(8) -0.0020(10)
  C15 0.0357(9) 0.089(2) 0.0510(10)
  -0.0240(10)
  0.0028(8) 0.0030(10)
  C16 0.0344(9) 0.092(2) 0.0670(10)
  -0.0330(10)
  0.0094(9) -0.0080(10)
  C17 0.0429(9) 0.073(2) 0.0660(10)
  -0.0250(10)
  0.0198(8) -0.0120(10)
  C18 0.0412(9) 0.0660(10)
  0.0510(10)
  -0.0170(10)
  0.0149(8) -0.0040(10)
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
  Cl1 C15 . . 1.750(2) yes
  Cl2 C17 . . 1.731(3) yes
  O1 C2 . . 1.222(3) yes
  O2 C4 . . 1.422(3) yes
  O2 C5 . . 1.422(3) yes
  O3 C8 . . 1.427(3) yes
  O3 C9 . . 1.416(3) yes
  O4 C18 . . 1.350(3) yes
  N1 C2 . . 1.343(2) yes
  N1 C3 . . 1.458(3) yes
  N1 C6 . . 1.460(3) yes
  N2 C1 . . 1.350(3) yes
  N2 C7 . . 1.465(3) yes
  N2 C10 . . 1.473(3) yes
  N3 N4 . . 1.292(2) yes
  N3 C11 . . 1.376(3) yes
  N4 C13 . . 1.413(3) yes
  C1 C2 . . 1.520(3) yes
  C1 C11 . . 1.381(3) yes
  C3 C4 . . 1.513(3) yes
  C5 C6 . . 1.508(3) yes
  C7 C8 . . 1.497(4) yes
  C9 C10 . . 1.500(4) yes
  C11 C12 . . 1.490(3) yes
  C13 C14 . . 1.393(3) yes
  C13 C18 . . 1.409(3) yes
  C14 C15 . . 1.378(3) yes
  C15 C16 . . 1.379(4) yes
  C16 C17 . . 1.375(4) yes
  C17 C18 . . 1.400(3) yes
  O4 H4O . . 0.87(3) no
  C3 H31 . . 0.91(2) no
  C3 H32 . . 1.05(2) no
  C4 H41 . . 0.98(2) no
  C4 H42 . . 1.01(2) no
  C5 H51 . . 1.01(2) no
  C5 H52 . . 0.97(2) no
  C6 H61 . . 0.97(2) no
  C6 H62 . . 1.04(2) no
  C7 H71 . . 0.97(2) no
  C7 H72 . . 1.01(2) no
  C8 H81 . . 0.94(3) no
  C8 H82 . . 0.97(2) no
  C9 H91 . . 1.02(3) no
  C9 H92 . . 1.02(2) no
  C10 H101 . . 0.99(3) no
  C10 H102 . . 0.98(2) no
  C12 H121 . . 0.98(2) no
  C12 H122 . . 0.97(2) no
  C12 H123 . . 1.05(2) no
  C14 H14 . . 0.97(2) no
  C16 H16 . . 0.91(2) no