#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008197.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_2008197
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  245
_journal_page_last  248
_publ_section_title
;
 4-Chloro-2-[2-(dimethylamino)ethylaminomethyl]phenol and
 2-[2-(dimethylamino)ethylaminomethyl]-6-methoxyphenol
;
loop_
_publ_author_name
  'Lian Ee Khoo'
  'Hong Juan Hu'
  'Alan Hazell'
_chemical_formula_sum  'C12 H20 N2 O2'
_chemical_formula_weight  224.310
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  '+x,+y,+z'
  '1/2+x,1/2-y,-z'
  '-x,1/2+y,1/2-z'
  '1/2-x,-y,1/2+z'
  '-x,-y,-z'
  '1/2-x,1/2+y,+z'
  '+x,1/2-y,1/2+z'
  '1/2+x,+y,1/2-z'
_cell_length_a  15.9034(8)
_cell_length_b  10.5054(5)
_cell_length_c  16.1559(8)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  2699.2(2)
_cell_formula_units_Z  8
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.104
_diffrn_ambient_temperature  298
_refine_ls_R_factor_obs  0.048
_refine_ls_wR_factor_obs  0.056
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
  O1 0.27700(10)
  0.33640(10)
  0.12000(10)
  0.0700(10)
  Uij
  O2 0.36990(10)
  0.54720(10)
  0.10000(10)
  0.1130(10)
  Uij
  N1 0.31450(10)
  0.04860(10)
  0.09360(10)
  0.0560(10)
  Uij
  N2 0.31420(10)
  0.0911(2) -0.08330(10)
  0.0850(10)
  Uij
  C1 0.35980(10)
  0.3342(2) 0.13780(10)
  0.0560(10)
  Uij
  C2 0.41100(10)
  0.4413(2) 0.12850(10)
  0.0730(10)
  Uij
  C3 0.49480(10)
  0.4356(2) 0.1482(2) 0.090(2) Uij
  C4 0.52860(10)
  0.3240(2) 0.1769(2) 0.094(2) Uij
  C5 0.47950(10)
  0.2181(2) 0.18530(10)
  0.0760(10)
  Uij
  C6 0.39460(10)
  0.2210(2) 0.16590(10)
  0.0560(10)
  Uij
  C7 0.33960(10)
  0.1049(2) 0.17270(10)
  0.0630(10)
  Uij
  C8 0.38460(10)
  0.0111(2) 0.04060(10)
  0.0640(10)
  Uij
  C9 0.35400(10)
  -0.0186(2) -0.04430(10)
  0.0800(10)
  Uij
  C10 0.3745(2) 0.1893(3) -0.1028(2) 0.139(3) Uij
  C11 0.2701(2) 0.0516(4) -0.1578(2) 0.155(3) Uij
  C12 0.4138(2) 0.6557(3) 0.0791(2) 0.137(3) Uij
  HO1 0.255(2) 0.416(3) 0.1130(10)
  0.104(8) Uiso
  HN1 0.2860(10)
  0.101(2) 0.0690(10)
  0.050(5) Uiso
  H3 0.5293 0.5088 0.1420 0.108 Uiso
  H4 0.5865 0.3203 0.1910 0.113 Uiso
  H5 0.5040 0.1412 0.2047 0.091 Uiso
  H7a 0.3694 0.0422 0.2033 0.075 Uiso
  H7b 0.2901 0.1280 0.2019 0.075 Uiso
  H8a 0.4110 -0.0621 0.0632 0.077 Uiso
  H8b 0.4240 0.0789 0.0378 0.077 Uiso
  H9a 0.4003 -0.0448 -0.0772 0.095 Uiso
  H9b 0.3142 -0.0859 -0.0410 0.095 Uiso
  H10a 0.3485 0.2607 -0.1283 0.167 Uiso
  H10b 0.4154 0.1554 -0.1395 0.167 Uiso
  H10c 0.4010 0.2161 -0.0531 0.167 Uiso
  H11a 0.2441 0.1231 -0.1831 0.185 Uiso
  H11b 0.2282 -0.0092 -0.1436 0.185 Uiso
  H11c 0.3089 0.0144 -0.1952 0.185 Uiso
  H12a 0.3853 0.7291 0.0593 0.164 Uiso
  H12b 0.4525 0.6318 0.0371 0.164 Uiso
  H12c 0.4437 0.6811 0.1272 0.164 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
  O1 0.0580(10)
  0.0430(10)
  0.1100(10)
  -0.0010(10)
  -0.0100(10)
  0.0070(10)
  O2 0.0790(10)
  0.0480(10)
  0.212(2) -0.0110(10)
  -0.0130(10)
  0.0240(10)
  N1 0.0590(10)
  0.0410(10)
  0.0670(10)
  0.0030(10)
  0.0040(10)
  0.0050(10)
  N2 0.0750(10)
  0.114(2) 0.0670(10)
  -0.0120(10)
  -0.0060(10)
  0.0050(10)
  C1 0.0570(10)
  0.0470(10)
  0.0640(10)
  -0.0010(10)
  -0.0040(10)
  -0.0070(10)
  C2 0.0650(10)
  0.0500(10)
  0.103(2) -0.0040(10)
  -0.0030(10)
  -0.0080(10)
  C3 0.0660(10)
  0.0690(10)
  0.134(2) -0.0120(10)
  -0.0040(10)
  -0.0200(10)
  C4 0.0600(10)
  0.093(2) 0.130(2) 0.0040(10)
  -0.0180(10)
  -0.024(2)
  C5 0.0750(10)
  0.0730(10)
  0.0810(10)
  0.0160(10)
  -0.0150(10)
  -0.0120(10)
  C6 0.0660(10)
  0.0520(10)
  0.0510(10)
  0.0060(10)
  -0.0020(10)
  -0.0070(10)
  C7 0.0800(10)
  0.0520(10)
  0.0570(10)
  0.0080(10)
  0.0060(10)
  0.0080(10)
  C8 0.0620(10)
  0.0530(10)
  0.0770(10)
  0.0060(10)
  0.0020(10)
  -0.0070(10)
  C9 0.0730(10)
  0.083(2) 0.0830(10)
  -0.0100(10)
  0.0070(10)
  -0.0250(10)
  C10 0.152(3) 0.148(3) 0.117(2) -0.046(2) -0.009(2) 0.048(2)
  C11 0.120(3) 0.241(5) 0.102(2) -0.032(3) -0.033(2) -0.003(2)
  C12 0.126(2) 0.067(2) 0.217(4) -0.023(2) -0.001(2) 0.032(2)
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
  O1 C1 . . 1.348(2) yes
  O2 C2 . . 1.369(2) yes
  O2 C12 . . 1.379(3) yes
  N1 C8 . . 1.460(2) yes
  N1 C7 . . 1.463(3) yes
  N2 C10 . . 1.444(4) no
  N2 C11 . . 1.452(4) no
  N2 C9 . . 1.459(3) no
  C1 C6 . . 1.388(2) no
  C1 C2 . . 1.397(3) no
  C2 C3 . . 1.372(3) no
  C3 C4 . . 1.370(3) no
  C4 C5 . . 1.365(3) no
  C5 C6 . . 1.387(3) no
  C6 C7 . . 1.505(3) yes
  C8 C9 . . 1.488(3) no
  O1 HO1 . . 0.92(3) no
  N1 HN1 . . 0.81(2) no
  C3 H3 . . 0.950 no
  C4 H4 . . 0.950 no
  C5 H5 . . 0.950 no
  C7 H7a . . 0.950 no
  C7 H7b . . 0.950 no
  C8 H8a . . 0.950 no
  C8 H8b . . 0.950 no
  C9 H9a . . 0.950 no
  C9 H9b . . 0.950 no
  C10 H10b . . 0.950 no
  C10 H10c . . 0.950 no
  C10 H10a . . 0.950 no
  C11 H11b . . 0.950 no
  C11 H11a . . 0.950 no
  C11 H11c . . 0.950 no
  C12 H12a . . 0.950 no
  C12 H12b . . 0.950 no
  C12 H12c . . 0.950 no