#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014638.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_2014638
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2005
_journal_volume  61
_journal_page_first  o148
_journal_page_last  o150
_publ_section_title
;
3-Acetoxy-2-(acetylamino)pyridinium-1-squarate
;
loop_
_publ_author_name
  "U\,car, \.Ibrahim"
  'Bulut, Ahmet'
  "Ye\,silel, Okan Zafer"
  "Odaba\,soglu, Mustafa"
  "B\"uy\"ukg\"ung\"or, Orhan"
_chemical_formula_moiety  'C13 H10 N2 O6'
_chemical_formula_sum  'C13 H10 N2 O6'
_chemical_formula_iupac  'C13 H10 N2 O6'
_chemical_formula_weight  290.23
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  8.8959(16)
_cell_length_b  8.9014(16)
_cell_length_c  8.9288(16)
_cell_angle_alpha  88.895(15)
_cell_angle_beta  87.795(15)
_cell_angle_gamma  66.667(14)
_cell_volume  648.7(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.486
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  C1 0.1598(5) 0.4645(4) 0.7452(4) 0.0387(9) Uani d . 1 . . C
  C2 0.1712(5) 0.4275(5) 0.9028(5) 0.0463(10) Uani d . 1 . . C
  C3 0.1503(6) 0.2713(5) 0.8675(5) 0.0507(11) Uani d . 1 . . C
  C4 0.1389(5) 0.3220(4) 0.7035(4) 0.0397(9) Uani d . 1 . . C
  C5 0.1245(5) 0.7430(5) 0.7549(4) 0.0468(10) Uani d . 1 . . C
  H5 0.0875 0.7436 0.8537 0.056 Uiso calc R 1 . . H
  C6 0.1368(5) 0.8782(5) 0.6964(5) 0.0494(11) Uani d . 1 . . C
  H6 0.1134 0.9695 0.7563 0.059 Uiso calc R 1 . . H
  C7 0.1841(5) 0.8817(5) 0.5472(5) 0.0457(10) Uani d . 1 . . C
  H7 0.1932 0.9748 0.5064 0.055 Uiso calc R 1 . . H
  C8 0.2171(5) 0.7469(4) 0.4614(4) 0.0390(9) Uani d . 1 . . C
  C9 0.2157(5) 0.6018(4) 0.5227(4) 0.0362(9) Uani d . 1 . . C
  C10 0.3865(5) 0.3874(4) 0.3475(4) 0.0395(9) Uani d . 1 . . C
  C11 0.3994(6) 0.2277(5) 0.2900(5) 0.0591(13) Uani d . 1 . . C
  H11A 0.4985 0.1792 0.2300 0.089 Uiso calc R 1 . . H
  H11B 0.3069 0.2438 0.2301 0.089 Uiso calc R 1 . . H
  H11C 0.4012 0.1566 0.3728 0.089 Uiso calc R 1 . . H
  C12 0.3697(6) 0.7824(5) 0.2508(5) 0.0490(11) Uani d . 1 . . C
  C13 0.3782(7) 0.7723(7) 0.0848(5) 0.0763(16) Uani d . 1 . . C
  H13A 0.3130 0.8775 0.0434 0.114 Uiso calc R 1 . . H
  H13B 0.3371 0.6934 0.0540 0.114 Uiso calc R 1 . . H
  H13C 0.4899 0.7397 0.0495 0.114 Uiso calc R 1 . . H
  N1 0.1660(4) 0.6046(3) 0.6706(3) 0.0367(8) Uani d . 1 . . N
  N2 0.2535(4) 0.4586(4) 0.4465(3) 0.0396(8) Uani d . 1 . . N
  H2 0.1892 0.4084 0.4612 0.048 Uiso calc R 1 . . H
  O1 0.1876(4) 0.4925(4) 1.0171(3) 0.0620(9) Uani d . 1 . . O
  O2 0.1430(5) 0.1577(4) 0.9380(4) 0.0777(11) Uani d . 1 . . O
  O3 0.1200(4) 0.2617(3) 0.5851(3) 0.0484(8) Uani d . 1 . . O
  O4 0.2387(3) 0.7502(3) 0.3077(3) 0.0443(7) Uani d . 1 . . O
  O5 0.4594(4) 0.8134(4) 0.3293(4) 0.0637(9) Uani d . 1 . . O
  O6 0.4830(4) 0.4497(3) 0.3171(3) 0.0520(8) Uani d . 1 . . O
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
  C1 0.037(2) 0.039(2) 0.039(2) -0.0132(18) 0.0002(17) -0.0025(17)
  C2 0.047(3) 0.041(2) 0.046(2) -0.012(2) 0.003(2) -0.0028(19)
  C3 0.059(3) 0.043(2) 0.048(2) -0.017(2) 0.000(2) -0.001(2)
  C4 0.036(2) 0.034(2) 0.047(2) -0.0125(18) 0.0041(18) -0.0040(17)
  C5 0.055(3) 0.042(2) 0.040(2) -0.016(2) 0.006(2) -0.0129(18)
  C6 0.057(3) 0.035(2) 0.056(3) -0.018(2) -0.001(2) -0.0090(19)
  C7 0.044(3) 0.033(2) 0.061(3) -0.0161(19) -0.009(2) 0.0017(19)
  C8 0.037(2) 0.036(2) 0.043(2) -0.0123(18) -0.0070(18) 0.0048(17)
  C9 0.029(2) 0.039(2) 0.039(2) -0.0120(17) -0.0048(17) -0.0028(17)
  C10 0.042(3) 0.039(2) 0.033(2) -0.010(2) -0.0028(19) 0.0001(16)
  C11 0.073(3) 0.047(2) 0.050(3) -0.015(2) 0.009(2) -0.011(2)
  C12 0.051(3) 0.045(2) 0.050(3) -0.017(2) -0.001(2) 0.0083(19)
  C13 0.088(4) 0.091(4) 0.050(3) -0.036(3) 0.000(3) 0.014(3)
  N1 0.039(2) 0.0355(17) 0.0356(18) -0.0148(15) 0.0004(15) -0.0049(13)
  N2 0.042(2) 0.0369(17) 0.0437(18) -0.0194(15) -0.0002(16) -0.0062(14)
  O1 0.085(2) 0.0593(19) 0.0426(17) -0.0285(17) -0.0102(16) -0.0039(14)
  O2 0.124(3) 0.0492(19) 0.061(2) -0.037(2) 0.008(2) 0.0074(16)
  O3 0.060(2) 0.0484(16) 0.0481(17) -0.0326(15) -0.0007(14) -0.0068(13)
  O4 0.0462(18) 0.0460(16) 0.0414(16) -0.0187(14) -0.0060(13) 0.0059(12)
  O5 0.062(2) 0.071(2) 0.069(2) -0.0384(18) 0.0017(17) -0.0003(16)
  O6 0.0434(19) 0.0526(17) 0.0569(18) -0.0162(15) 0.0017(15) 0.0035(13)
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
  C1 C4 . 1.411(5) y
  C1 N1 . 1.422(5) y
  C1 C2 . 1.437(5) y
  C2 O1 . 1.224(4) y
  C2 C3 . 1.515(6) y
  C3 O2 . 1.202(5) y
  C3 C4 . 1.519(6) y
  C4 O3 . 1.242(4) y
  C5 C6 . 1.344(6) ?
  C5 N1 . 1.369(5) ?
  C5 H5 . 0.9300 ?
  C6 C7 . 1.385(6) ?
  C6 H6 . 0.9300 ?
  C7 C8 . 1.361(5) ?
  C7 H7 . 0.9300 ?
  C8 O4 . 1.380(4) ?
  C8 C9 . 1.398(5) ?
  C9 N2 . 1.370(4) ?
  C9 N1 . 1.374(5) ?
  C10 O6 . 1.212(5) y
  C10 N2 . 1.389(5) ?
  C10 C11 . 1.480(5) ?
  C11 H11A . 0.9600 ?
  C11 H11B . 0.9600 ?
  C11 H11C . 0.9600 ?
  C12 O5 . 1.195(5) ?
  C12 O4 . 1.383(5) ?
  C12 C13 . 1.484(6) ?
  C13 H13A . 0.9600 ?
  C13 H13B . 0.9600 ?
  C13 H13C . 0.9600 ?
  N2 H2 . 0.8600 ?
_cod_database_code 2014638