#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008196.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_2008196
_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  'C11 H17 Cl N2 O'
_chemical_formula_weight  228.73
_chemical_melting_point  335-338K
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  '+x,+y,+z'
  '1/2-x,1/2-y,1/2+z'
  '1/2+x,1/2-y,-z'
  '-x,+y,1/2-z'
  '-x,-y,-z'
  '1/2+x,1/2+y,1/2-z'
  '1/2-x,1/2+y,+z'
  '+x,-y,1/2+z'
_cell_length_a  21.9350(10)
_cell_length_b  11.4354(7)
_cell_length_c  9.9743(6)
_cell_angle_alpha  90.0
_cell_angle_beta  90.0
_cell_angle_gamma  90.0
_cell_volume  2501.9(2)
_cell_formula_units_Z  8
_cell_measurement_temperature  295
_exptl_crystal_density_diffrn  1.214
_diffrn_ambient_temperature  295
_refine_ls_R_factor_obs  0.041
_refine_ls_wR_factor_obs  0.046
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
  Cl 0.92040(4) 0.55243(5) 1.16671(7) 0.0720(5) Uij
  O1 0.92920(10)
  0.04020(10)
  1.1492(2) 0.0580(10)
  Uij
  C1 0.92690(10)
  0.1580(2) 1.1587(2) 0.0410(10)
  Uij
  C2 0.91510(10)
  0.2168(2) 1.2776(2) 0.050(2) Uij
  C3 0.91330(10)
  0.3374(2) 1.2806(2) 0.051(2) Uij
  C4 0.92330(10)
  0.3994(2) 1.1647(2) 0.0450(10)
  Uij
  C5 0.93560(10)
  0.3424(2) 1.0459(2) 0.0420(10)
  Uij
  C6 0.93810(10)
  0.2214(2) 1.0413(2) 0.0370(10)
  Uij
  C7 0.95150(10)
  0.1563(2) 0.9135(2) 0.0460(10)
  Uij
  N1 0.89950(10)
  0.0892(2) 0.8605(2) 0.0490(10)
  Uij
  C8 0.85010(10)
  0.1637(2) 0.8096(2) 0.060(2) Uij
  C9 0.79150(10)
  0.0951(2) 0.8021(3) 0.070(2) Uij
  N2 0.77240(10)
  0.0515(2) 0.9324(3) 0.064(2) Uij
  C10 0.74970(10)
  0.1441(3) 1.0171(3) 0.088(2) Uij
  C11 0.7269(2) -0.0402(3) 0.9182(4) 0.101(3) Uij
  HN1 0.8850(10)
  0.053(2) 0.923(2) 0.044(8) Uiso
  HO1 0.9190(10)
  0.006(3) 1.228(3) 0.083(10) Uiso
  H2 0.9083 0.1737 1.3576 0.060 Uiso
  H3 0.9053 0.3772 1.3623 0.061 Uiso
  H5 0.9425 0.3865 0.9666 0.050 Uiso
  H7a 0.9636 0.2115 0.8475 0.056 Uiso
  H7b 0.9840 0.1035 0.9302 0.056 Uiso
  H8a 0.8448 0.2285 0.8680 0.072 Uiso
  H8b 0.8605 0.1911 0.7226 0.072 Uiso
  H9a 0.7604 0.1445 0.7676 0.084 Uiso
  H9b 0.7972 0.0306 0.7435 0.084 Uiso
  H10a 0.7372 0.1155 1.1023 0.106 Uiso
  H10b 0.7810 0.2004 1.0295 0.106 Uiso
  H10c 0.7157 0.1798 0.9744 0.106 Uiso
  H11a 0.7144 -0.0687 1.0034 0.122 Uiso
  H11b 0.6924 -0.0095 0.8725 0.122 Uiso
  H11c 0.7437 -0.1028 0.8677 0.122 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
  Cl 0.1080(6) 0.0416(4) 0.0664(5) -0.0031(4) 0.0002(4) -0.0112(3)
  O1 0.0920(10)
  0.0390(10)
  0.0420(10)
  0.0120(10)
  0.0140(10)
  0.0100(10)
  C1 0.0470(10)
  0.0400(10)
  0.0360(10)
  0.0060(10)
  0.0040(10)
  0.0020(10)
  C2 0.066(2) 0.052(2) 0.0310(10)
  0.0060(10)
  0.0050(10)
  0.0040(10)
  C3 0.064(2) 0.056(2) 0.0340(10)
  0.0040(10)
  0.0020(10)
  -0.0100(10)
  C4 0.052(2) 0.0400(10)
  0.0430(10)
  -0.0010(10)
  -0.0010(10)
  -0.0070(10)
  C5 0.0470(10)
  0.0420(10)
  0.0370(10)
  -0.0010(10)
  0.0000(10)
  0.0040(10)
  C6 0.0400(10)
  0.0410(10)
  0.0310(10)
  0.0030(10)
  0.0030(10)
  0.0000(10)
  C7 0.058(2) 0.0430(10)
  0.0370(10)
  0.0040(10)
  0.0120(10)
  0.0000(10)
  N1 0.073(2) 0.0370(10)
  0.0360(10)
  0.0020(10)
  0.0070(10)
  -0.0010(10)
  C8 0.083(2) 0.049(2) 0.049(2) 0.0000(10)
  -0.0070(10)
  0.0050(10)
  C9 0.085(2) 0.061(2) 0.064(2) -0.006(2) -0.020(2) -0.0030(10)
  N2 0.072(2) 0.0510(10)
  0.070(2) -0.0090(10)
  -0.0100(10)
  0.0060(10)
  C10 0.099(3) 0.084(2) 0.081(2) 0.005(2) 0.006(2) 0.007(2)
  C11 0.094(3) 0.076(2) 0.133(3) -0.023(2) -0.017(2) 0.014(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
  Cl C4 . . 1.751(2) yes
  O1 C1 . . 1.352(3) yes
  C1 C2 . . 1.387(3) no
  C1 C6 . . 1.399(3) no
  C2 C3 . . 1.379(3) no
  C3 C4 . . 1.374(3) no
  C4 C5 . . 1.379(3) no
  C5 C6 . . 1.385(3) no
  C6 C7 . . 1.505(3) yes
  C7 N1 . . 1.472(3) yes
  N1 C8 . . 1.469(3) yes
  C8 C9 . . 1.509(4) no
  C9 N2 . . 1.454(4) no
  N2 C10 . . 1.443(4) no
  N2 C11 . . 1.456(4) no
  O1 HO1 . . 0.90(3) no
  C2 H2 . . 0.950 no
  C3 H3 . . 0.950 no
  C5 H5 . . 0.950 no
  C7 H7a . . 0.950 no
  C7 H7b . . 0.950 no
  N1 HN1 . . 0.81(2) no
  N1 HO1 . 8_554 1.77(3) no
  C8 H8a . . 0.950 no
  C8 H8b . . 0.950 no
  C9 H9a . . 0.950 no
  C9 H9b . . 0.950 no
  C10 H10a . . 0.950 no
  C10 H10b . . 0.950 no
  C10 H10c . . 0.950 no
  C11 H11a . . 0.950 no
  C11 H11b . . 0.950 no
  C11 H11c . . 0.950 no