#------------------------------------------------------------------------------
#$Date: 2009-11-18 14:56:34 +0000 (Wed, 18 Nov 2009) $
#$Revision: 858 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006019.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_2006019
_journal_name_full 'Acta Crystallographica Section C'
_journal_year       1997
_journal_volume 53
_journal_page_first 331
_journal_page_last 334
_publ_section_title
;
N-(Carbamoylmethyl)pyridinium Perchlorate and
N-(Carbamoylmethyl)-N'-methyl-4,4'-bipyridinium Diperchlorate Hydrate
;
_chemical_formula_moiety 'C13 H15 N3 O, (Cl O4)2, H2 O'
_chemical_formula_sum            'C13 H17 Cl2 N3 O10'
_[local]_cod_chemical_formula_sum_orig 'C13 Cl2 H17 N3 O10'
_chemical_formula_weight 446.20
_symmetry_cell_setting monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  ' +x, +y, +z'
  ' -x,1/2+y,1/2-z'
  ' -x, -y, -z'
  ' +x,1/2-y,1/2+z'
_cell_length_a 11.528(3)
_cell_length_b 8.643(3)
_cell_length_c 19.141(2)
_cell_angle_alpha 90
_cell_angle_beta 106.56(1)
_cell_angle_gamma 90
_cell_volume 1828.0(8)
_cell_formula_units_Z 4
_exptl_crystal_density_diffrn 1.621
_cell_measurement_temperature 296.0
_refine_ls_R_factor_obs 0.0569
_refine_ls_wR_factor_obs 0.0624
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
  Cl(1) 1.2979(1) 1.0627(2) 0.58568(8) 0.0552(5)
  Cl(2) 0.8655(1) 0.4485(2) 0.21326(7) 0.0474(4)
  O(1) 1.5513(3) 0.4147(4) 0.3058(2) 0.054(1)
  O(2) 1.4116(5) 1.0266(8) 0.5785(4) 0.168(3)
  O(3) 1.2919(6) 0.9885(7) 0.6486(3) 0.145(3)
  O(4) 1.2888(5) 1.2201(6) 0.5929(3) 0.138(2)
  O(5) 1.2078(4) 1.0077(6) 0.5251(2) 0.104(2)
  O(6) 0.8866(4) 0.5486(6) 0.2742(3) 0.102(2)
  O(7) 0.7864(4) 0.5190(6) 0.1519(2) 0.099(2)
  O(8) 0.8119(4) 0.3125(5) 0.2298(3) 0.102(2)
  O(9) 0.9758(4) 0.4081(6) 0.1996(3) 0.093(2)
  O(10) 1.4002(4) 0.7816(6) 0.4471(3) 0.106(2)
  N(1) 1.0749(4) 0.7198(5) 0.5530(2) 0.048(1)
  N(2) 1.3494(4) 0.3012(5) 0.3307(2) 0.041(1)
  N(3) 1.5592(5) 0.2272(7) 0.2244(3) 0.057(2)
  C(1) 1.0262(5) 0.7184(7) 0.4808(3) 0.057(2)
  C(2) 1.0806(5) 0.6421(7) 0.4361(3) 0.054(2)
  C(3) 1.1882(4) 0.5632(6) 0.4656(3) 0.039(1)
  C(4) 1.2367(5) 0.5683(7) 0.5402(3) 0.046(2)
  C(5) 1.1799(5) 0.6468(7) 0.5829(3) 0.051(2)
  C(6) 1.3980(5) 0.2985(7) 0.4028(3) 0.057(2)
  C(7) 1.3475(5) 0.3845(7) 0.4472(3) 0.058(2)
  C(8) 1.2468(4) 0.4742(6) 0.4183(3) 0.038(1)
  C(9) 1.2005(5) 0.4773(7) 0.3436(3) 0.049(2)
  C(10) 1.2525(5) 0.3885(7) 0.3010(3) 0.053(2)
  C(11) 1.0164(8) 0.8078(10) 0.6006(5) 0.066(3)
  C(12) 1.4049(6) 0.2100(7) 0.2838(4) 0.048(2)
  C(13) 1.5134(4) 0.2956(6) 0.2726(3) 0.042(2)
  H(1) 0.950(4) 0.777(6) 0.460(3) 0.06(2)
  H(2) 1.043(4) 0.647(6) 0.386(3) 0.05(2)
  H(3) 1.309(4) 0.519(5) 0.560(2) 0.05(2)
  H(4) 1.210(4) 0.650(6) 0.633(3) 0.05(2)
  H(5) 1.467(5) 0.226(7) 0.421(3) 0.08(2)
  H(6) 1.381(4) 0.378(6) 0.497(3) 0.05(2)
  H(7) 1.130(4) 0.535(6) 0.321(3) 0.05(2)
  H(8) 1.224(4) 0.396(6) 0.252(3) 0.05(2)
  H(9) 0.942(6) 0.820(8) 0.579(3) 0.09(2)
  H(10) 1.049(7) 0.893(8) 0.612(4) 0.11(3)
  H(11) 1.031(7) 0.745(10) 0.646(4) 0.14(3)
  H(12) 1.347(4) 0.187(6) 0.241(3) 0.06(2)
  H(13) 1.425(4) 0.114(6) 0.306(3) 0.04(2)
  H(14) 1.522(6) 0.136(8) 0.200(3) 0.09(2)
  H(15) 1.615(6) 0.265(8) 0.217(3) 0.08(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
  Cl(1) 1_555 O(2) 1_555 1.391(5)
  Cl(1) 1_555 O(3) 1_555 1.383(5)
  Cl(1) 1_555 O(4) 1_555 1.374(5)
  Cl(1) 1_555 O(5) 1_555 1.401(4)
  Cl(2) 1_555 O(6) 1_555 1.416(4)
  Cl(2) 1_555 O(7) 1_555 1.404(4)
  Cl(2) 1_555 O(8) 1_555 1.405(4)
  Cl(2) 1_555 O(9) 1_555 1.413(4)
  O(1) 1_555 C(13) 1_555 1.223(6)
  N(1) 1_555 C(1) 1_555 1.335(7)
  N(1) 1_555 C(5) 1_555 1.340(7)
  N(1) 1_555 C(11) 1_555 1.489(7)
  N(2) 1_555 C(6) 1_555 1.334(7)
  N(2) 1_555 C(10) 1_555 1.333(7)
  N(2) 1_555 C(12) 1_555 1.472(6)
  N(3) 1_555 C(13) 1_555 1.325(7)
  N(3) 1_555 H(14) 1_555 0.96(7)
  N(3) 1_555 H(15) 1_555 0.77(6)
  C(1) 1_555 C(2) 1_555 1.366(7)
  C(1) 1_555 H(1) 1_555 1.00(5)
  C(2) 1_555 C(3) 1_555 1.386(7)
  C(2) 1_555 H(2) 1_555 0.94(4)
  C(3) 1_555 C(4) 1_555 1.379(7)
  C(3) 1_555 C(8) 1_555 1.488(7)
  C(4) 1_555 C(5) 1_555 1.365(7)
  C(4) 1_555 H(3) 1_555 0.92(4)
  C(5) 1_555 H(4) 1_555 0.93(4)
  C(6) 1_555 C(7) 1_555 1.377(7)
  C(6) 1_555 H(5) 1_555 1.00(6)
  C(7) 1_555 C(8) 1_555 1.374(7)
  C(7) 1_555 H(6) 1_555 0.92(5)
  C(8) 1_555 C(9) 1_555 1.377(7)
  C(9) 1_555 C(10) 1_555 1.376(7)
  C(9) 1_555 H(7) 1_555 0.95(5)
  C(10) 1_555 H(8) 1_555 0.91(5)
  C(11) 1_555 H(9) 1_555 0.84(6)
  C(11) 1_555 H(10) 1_555 0.83(7)
  C(11) 1_555 H(11) 1_555 1.00(8)
  C(12) 1_555 C(13) 1_555 1.520(7)
  C(12) 1_555 H(12) 1_555 0.93(5)
  C(12) 1_555 H(13) 1_555 0.93(5)
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
  Cl(1) 0.0510(9) 0.0003(8) 0.0168(7) 0.0555(9) 0.0071(8) 0.0598(9)
  Cl(2) 0.0419(8) -0.0003(7) 0.0192(6) 0.0495(8) 0.0000(7) 0.0540(8)
  O(1) 0.053(2) -0.007(2) 0.024(2) 0.045(2) -0.002(2) 0.067(3)
  O(2) 0.071(4) 0.023(4) 0.058(4) 0.199(7) -0.042(6) 0.244(8)
  O(3) 0.207(6) -0.054(5) 0.040(4) 0.145(6) 0.024(4) 0.082(4)
  O(4) 0.164(6) 0.013(4) -0.010(4) 0.056(3) 0.001(4) 0.159(6)
  O(5) 0.096(4) -0.017(3) -0.012(3) 0.119(4) 0.003(3) 0.076(3)
  O(6) 0.094(3) 0.006(3) 0.011(3) 0.110(4) -0.049(3) 0.093(3)
  O(7) 0.095(3) 0.049(3) 0.011(3) 0.116(4) 0.018(3) 0.078(3)
  O(8) 0.094(4) -0.030(3) 0.053(3) 0.079(4) 0.013(3) 0.145(5)
  O(9) 0.053(3) 0.015(3) 0.043(3) 0.123(4) 0.000(3) 0.114(4)
  O(10) 0.094(4) -0.006(3) 0.021(3) 0.102(4) 0.016(3) 0.118(4)
  N(1) 0.049(3) -0.002(2) 0.026(2) 0.043(3) -0.003(2) 0.058(3)
  N(2) 0.038(3) -0.004(2) 0.022(2) 0.041(3) -0.002(2) 0.051(3)
  N(3) 0.054(3) -0.006(3) 0.036(3) 0.060(4) -0.005(3) 0.068(4)
  C(1) 0.052(4) 0.013(3) 0.010(3) 0.061(4) -0.001(3) 0.054(4)
  C(2) 0.052(4) 0.016(3) 0.013(3) 0.066(4) -0.006(3) 0.044(4)
  C(3) 0.038(3) -0.003(3) 0.015(2) 0.037(3) 0.001(3) 0.043(3)
  C(4) 0.040(3) 0.006(3) 0.014(3) 0.049(3) 0.000(3) 0.049(3)
  C(5) 0.055(4) 0.000(3) 0.020(3) 0.054(4) 0.000(3) 0.047(4)
  C(6) 0.057(4) 0.016(3) 0.015(3) 0.063(4) -0.002(3) 0.051(4)
  C(7) 0.060(4) 0.019(3) 0.009(3) 0.070(4) -0.005(3) 0.039(3)
  C(8) 0.035(3) -0.003(2) 0.012(2) 0.038(3) 0.002(2) 0.042(3)
  C(9) 0.045(3) 0.010(3) 0.015(3) 0.056(4) 0.002(3) 0.048(3)
  C(10) 0.048(4) 0.002(3) 0.013(3) 0.069(4) 0.000(3) 0.042(4)
  C(11) 0.065(5) 0.011(4) 0.039(4) 0.073(5) -0.013(4) 0.072(5)
  C(12) 0.049(4) -0.009(3) 0.029(3) 0.042(4) -0.013(3) 0.062(4)
  C(13) 0.038(3) 0.003(3) 0.012(3) 0.041(3) 0.008(3) 0.046(3)