#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006648.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_2006648
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1997
_journal_volume 53
_journal_page_first  1635
_journal_page_last  1637
_publ_section_title
;
The 1:1 Complex Formed by 2-Picoline N-Oxide and 3-Chlorobenzoic Acid
;
loop_
_publ_author_name
  'Moreno-Fuquen, Rodolfo'
  'Grajales-Tamayo, Mario'
  'Gambardella, Maria Teresa do Prado'
_chemical_formula_moiety  'C6 H7 N O , C7 H5 Cl O2'
_chemical_formula_sum  'C13 H12 N O3 Cl'
_chemical_formula_weight  265.69
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P n'
_cell_length_a  3.9241(3)
_cell_length_b  13.0404(8)
_cell_length_c  12.4181(5)
_cell_angle_alpha  90.00
_cell_angle_beta  92.210(10)
_cell_angle_gamma  90.00
_cell_volume  634.98(7)
_cell_formula_units_Z  2
_cell_measurement_temperature  295
_exptl_crystal_density_diffrn  1.390
_diffrn_ambient_temperature  295
_refine_ls_R_factor_obs  .0293
_refine_ls_wR_factor_obs  .1057
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_disorder_group
_atom_site_type_symbol
  Cl1  .9778(2)  .16075(7)  .15280(7)  .0781(3) Uani d . 1 . Cl
  C1 1.0617(8)  .1174(2)  .0237(2)  .0534(6) Uani d . 1 . C
  C2 1.2078(9)  .0221(2)  .0096(3)  .0647(8) Uani d . 1 . C
  H2 1.2634(9)  -.0195(2)  .0685(3)  .076 Uiso calc R 1 . H
  C3 1.2695(10)  -.0099(2)  -.0943(4)  .0696(8) Uani d . 1 . C
  H3 1.3656(10)  -.0740(2)  -.1053(4)  .076 Uiso calc R 1 . H
  C4 1.1899(8)  .0524(2)  -.1818(3)  .0593(7) Uani d . 1 . C
  H4 1.2356(8)  .0304(2)  -.2510(3)  .076 Uiso calc R 1 . H
  C5 1.0414(7)  .1480(2)  -.1664(2)  .0463(6) Uani d . 1 . C
  C6  .9766(7)  .1805(2)  -.0621(2)  .0455(5) Uani d . 1 . C
  H6  .8771(7)  .2441(2)  -.0506(2)  .076 Uiso calc R 1 . H
  C7  .9564(7)  .2141(2)  -.2611(2)  .0503(6) Uani d . 1 . C
  O1 1.0022(8)  .1882(2)  -.3526(2)  .0706(6) Uani d . 1 . O
  O2  .8215(8)  .3022(2)  -.2345(2)  .0701(7) Uani d . 1 . O
  HO2  .747(11)  .3314(16)  -.2890(4)  .076 Uiso calc R 1 . H
  O3  .6663(8)  .4313(2)  -.3801(2)  .0718(7) Uani d . 1 . O
  N1  .6364(6)  .4073(2)  -.4834(2)  .0505(5) Uani d . 1 . N
  C8  .4918(10)  .3175(2)  -.5143(3)  .0610(7) Uani d . 1 . C
  H8  .4208(10)  .2719(2)  -.4622(3)  .076 Uiso calc R 1 . H
  C9  .4482(9)  .2926(3)  -.6201(3)  .0709(9) Uani d . 1 . C
  H9  .3496(9)  .2303(3)  -.6403(3)  .076 Uiso calc R 1 . H
  C10  .5510(11)  .3604(3)  -.6971(3)  .0729(9) Uani d . 1 . C
  H10  .5216(11)  .3448(3)  -.7700(3)  .076 Uiso calc R 1 . H
  C11  .6989(9)  .4520(3)  -.6646(3)  .0654(8) Uani d . 1 . C
  H11  .7679(9)  .4984(3)  -.7163(3)  .076 Uiso calc R 1 . H
  C12  .7465(7)  .4761(2)  -.5563(2)  .0509(6) Uani d . 1 . C
  C13  .9073(10)  .5724(2)  -.5141(3)  .0682(8) Uani d . 1 . C
  H131  .974(6)  .6143(9)  -.5733(3)  .076 Uiso calc R 1 . H
  H132 1.105(4)  .5557(3)  -.4695(18)  .076 Uiso calc R 1 . H
  H133  .747(3)  .6092(10)  -.4723(18)  .076 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  .1049(7)  .0823(5)  .0468(4)  -.0083(5)  .0000(4)  .0077(4)
  C1  .0568(15)  .0486(13)  .0541(14)  -.0081(12)  -.0056(11)  .0056(12)
  C2  .063(2)  .0496(14)  .080(2)  .0005(12)  -.016(2)  .0148(14)
  C3  .068(2)  .0423(12)  .097(2)  .0064(13)  -.005(2)  -.0052(14)
  C4  .057(2)  .0474(13)  .073(2)  .0044(12)  .0045(13)  -.0121(13)
  C5  .0488(13)  .0408(12)  .0495(13)  -.0059(10)  .0035(10)  -.0030(9)
  C6  .0506(12)  .0395(11)  .0465(12)  -.0026(9)  .0028(10)  .0023(9)
  C7  .0578(15)  .0466(12)  .0465(13)  -.0060(11)  .0018(11)  -.0027(10)
  O1  .098(2)  .0665(12)  .0482(12)  -.0035(13)  .0103(11)  -.0056(10)
  O2  .115(2)  .0521(10)  .0433(9)  .0158(12)  .0034(12)  .0049(8)
  O3  .114(2)  .0573(11)  .0439(10)  .0089(13)  .0002(11)  .0046(9)
  N1  .0575(13)  .0466(10)  .0473(11)  .0083(10)  .0007(9)  .0070(8)
  C8  .066(2)  .0521(13)  .065(2)  -.0026(14)  .0018(14)  .0130(13)
  C9  .071(2)  .063(2)  .077(2)  -.001(2)  -.017(2)  -.006(2)
  C10  .091(3)  .079(2)  .048(2)  .013(2)  -.006(2)  -.0050(14)
  C11  .070(2)  .073(2)  .0539(15)  .014(2)  .0113(13)  .0158(14)
  C12  .0478(13)  .0490(12)  .0561(13)  .0081(11)  .0030(11)  .0123(11)
  C13  .071(2)  .0505(14)  .083(2)  .0013(14)  .001(2)  .0094(15)
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 C1 . 1.743(3) y
  C1 C6 . 1.376(4) y
  C1 C2 . 1.382(5) y
  C2 C3 . 1.386(6) y
  C3 C4 . 1.383(5) y
  C4 C5 . 1.392(4) y
  C5 C6 . 1.396(4) y
  C5 C7 . 1.485(4) y
  C7 O1 . 1.206(4) y
  C7 O2 . 1.313(4) y
  O3 N1 . 1.322(3) y
  N1 C8 . 1.350(4) y
  N1 C12 . 1.357(3) y
  C8 C9 . 1.358(5) y
  C9 C10 . 1.374(6) y
  C10 C11 . 1.382(6) y
  C11 C12 . 1.387(5) y
  C12 C13 . 1.492(5) y