#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2010169.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_2010169
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1994
_journal_volume 50
_journal_page_first  1774
_journal_page_last  1777
_publ_section_title
;
The Molecular Structure of Caroxazone, a Reversible Monoamine
Oxidase Inhibitor
;
loop_
_publ_author_name
  'Wouters, Johan'
  'Evrard, Guy'
  'Durant, Francois'
_chemical_name_common  'p-chlorophenylamidopentanoic acid'
_chemical_formula_moiety  'C12 H14 Cl N O3'
_chemical_formula_sum  'C12 H14 Cl N O3'
_chemical_formula_weight  255.69
_symmetry_cell_setting  'triclinic'
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  4.863(5)
_cell_length_b  9.963(3)
_cell_length_c  14.024(3)
_cell_angle_alpha  69.99(2)
_cell_angle_beta  76.70(4)
_cell_angle_gamma  80.28(4)
_cell_volume  618.2(7)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.374
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0432
_refine_ls_wR_factor_obs  0.1360
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_type_symbol
  Cl 0.3794(2) 0.85543(8) 0.11253(6) 0.1011(4) Uani d . 1 Cl
  N1 0.6621(3) 0.3153(2) 0.43434(13) 0.0429(4) Uani d . 1 N
  H1N 0.8378(3) 0.2945(2) 0.44003(13) 0.056(7) Uiso calc R 1 H
  O122 0.2039(3) -0.3811(2) 0.98004(13) 0.0719(6) Uani d . 1 O
  C10 0.5113(4) -0.1116(2) 0.7417(2) 0.0482(6) Uani d . 1 C
  H101 0.6680(4) -0.0901(2) 0.7643(2) 0.066(5) Uiso calc R 1 H
  H102 0.5853(4) -0.1803(2) 0.7047(2) 0.066(5) Uiso calc R 1 H
  O7 0.2251(3) 0.2392(2) 0.49571(12) 0.0609(5) Uani d . 1 O
  C1 0.5906(4) 0.4438(2) 0.35716(15) 0.0386(5) Uani d . 1 C
  C9 0.3884(4) 0.0246(2) 0.6693(2) 0.0495(6) Uani d . 1 C
  H91 0.3106(4) 0.0922(2) 0.7069(2) 0.068(5) Uiso calc R 1 H
  H92 0.2337(4) 0.0024(2) 0.6460(2) 0.068(5) Uiso calc R 1 H
  C2 0.3451(5) 0.5310(2) 0.3754(2) 0.0512(6) Uani d . 1 C
  H2 0.2227(5) 0.5046(2) 0.4389(2) 0.074(4) Uiso calc R 1 H
  C7 0.4780(4) 0.2231(2) 0.49938(15) 0.0416(5) Uani d . 1 C
  C11 0.2925(5) -0.1779(3) 0.8352(2) 0.0579(6) Uani d . 1 C
  H111 0.2292(5) -0.1108(3) 0.8740(2) 0.078(6) Uiso calc R 1 H
  H112 0.1296(5) -0.1911(3) 0.8116(2) 0.078(6) Uiso calc R 1 H
  C3 0.2804(5) 0.6566(2) 0.3002(2) 0.0602(6) Uani d . 1 C
  H3 0.1139(5) 0.7145(2) 0.3125(2) 0.074(4) Uiso calc R 1 H
  O121 0.6400(3) -0.3709(2) 0.89223(13) 0.0725(6) Uani d . 1 O
  C6 0.7712(5) 0.4853(3) 0.2634(2) 0.0568(6) Uani d . 1 C
  H6 0.9377(5) 0.4275(3) 0.2505(2) 0.074(4) Uiso calc R 1 H
  C4 0.4623(6) 0.6958(2) 0.2071(2) 0.0582(6) Uani d . 1 C
  C12 0.3928(4) -0.3186(2) 0.9063(2) 0.0498(6) Uani d . 1 C
  C8 0.6044(4) 0.0943(2) 0.5763(2) 0.0472(6) Uani d . 1 C
  H81 0.7508(4) 0.1238(2) 0.5995(2) 0.066(5) Uiso calc R 1 H
  H82 0.6939(4) 0.0240(2) 0.5422(2) 0.066(5) Uiso calc R 1 H
  C5 0.7074(6) 0.6120(3) 0.1881(2) 0.0677(7) Uani d . 1 C
  H5 0.8309(6) 0.6399(3) 0.1250(2) 0.074(4) 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
  Cl 0.1593(9) 0.0519(4) 0.0760(6) -0.0010(5) -0.0469(5) 0.0117(4)
  N1 0.0270(8) 0.0439(9) 0.0482(10) -0.0028(7) -0.0101(7) -0.0009(8)
  O122 0.0470(9) 0.0665(11) 0.0627(11) 0.0030(8) 0.0045(8) 0.0157(8)
  C10 0.0392(11) 0.0442(12) 0.0486(12) 0.0003(9) -0.0133(9) 0.0024(10)
  O7 0.0305(8) 0.0600(10) 0.0708(11) -0.0095(7) -0.0199(7) 0.0154(8)
  C1 0.0350(10) 0.0382(10) 0.0397(11) -0.0062(8) -0.0089(8) -0.0060(8)
  C9 0.0372(11) 0.0490(12) 0.0496(12) -0.0005(9) -0.0123(9) 0.0014(10)
  C2 0.0486(12) 0.0446(12) 0.0491(12) 0.0003(9) -0.0014(10) -0.0080(10)
  C7 0.0305(10) 0.0418(11) 0.0448(11) -0.0042(8) -0.0110(8) -0.0012(9)
  C11 0.0428(12) 0.0536(13) 0.0556(14) 0.0046(10) -0.0089(10) 0.0056(11)
  C3 0.0601(14) 0.0419(12) 0.069(2) 0.0089(10) -0.0170(12) -0.0095(11)
  O121 0.0419(9) 0.0705(11) 0.0645(11) 0.0092(8) -0.0032(7) 0.0185(9)
  C6 0.0504(13) 0.0502(13) 0.0543(14) -0.0011(10) 0.0038(11) -0.0075(11)
  C4 0.083(2) 0.0370(12) 0.0522(13) -0.0033(11) -0.0236(12) -0.0050(10)
  C12 0.0399(12) 0.0526(13) 0.0435(11) -0.0028(9) -0.0076(9) 0.0007(10)
  C8 0.0335(10) 0.0435(11) 0.0540(12) -0.0037(8) -0.0156(9) 0.0030(10)
  C5 0.087(2) 0.0572(15) 0.0418(13) -0.0144(13) 0.0045(12) -0.0009(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
  Cl C4 1.742(2) Yes
  N1 C7 1.343(3) Yes
  N1 C1 1.416(3) Yes
  N1 H1N 0.86 No
  O122 C12 1.272(3) Yes
  C10 C9 1.513(3) Yes
  C10 C11 1.513(3) Yes
  C10 H101 0.97 No
  C10 H102 0.97 No
  O7 C7 1.224(3) Yes
  C1 C6 1.375(3) Yes
  C1 C2 1.380(3) Yes
  C9 C8 1.511(3) Yes
  C9 H91 0.97 No
  C9 H92 0.97 No
  C2 C3 1.376(3) Yes
  C2 H2 0.93 No
  C7 C8 1.510(3) Yes
  C11 C12 1.494(3) Yes
  C11 H111 0.97 No
  C11 H112 0.97 No
  C3 C4 1.370(4) Yes
  C3 H3 0.93 No
  O121 C12 1.227(3) Yes
  C6 C5 1.383(3) Yes
  C6 H6 0.93 No
  C4 C5 1.364(4) Yes
  C8 H81 0.97 No
  C8 H82 0.97 No
  C5 H5 0.93 No