#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006319.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_2006319
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1997
_journal_volume 53
_journal_page_first  986
_journal_page_last  987
_publ_section_title
;
 Bis(dicyclohexylammonium) 2,6-Pyridinedicarboxylate Dihydrate
;
loop_
_publ_author_name
 'Ng, Seik Weng'
_chemical_formula_moiety  '2[C~12~H~24~N] [C~7~H3~NO~4~] 2OH~2~'
_chemical_formula_sum  'C31 H55 N3 O6'
_chemical_formula_iupac  '2C12 H24 N + , C7 H3 N O4 2- , 2H2 O'
_chemical_formula_weight  565.78
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
_cell_length_a  10.5790(10)
_cell_length_b  18.1356(9)
_cell_length_c  17.507(2)
_cell_angle_alpha  90.00
_cell_angle_beta  106.044(6)
_cell_angle_gamma  90.00
_cell_volume  3228.1(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.164
_diffrn_ambient_temperature  298(2)
_refine_ls_R_factor_obs   .0672
_refine_ls_wR_factor_obs   .1748
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
 O1  .5831(2)  .20820(10)
 -.22720(10)
   .0643(6) Uani d . 1 . O
 O2  .7142(2)  .1375(2)  -.1400(2)  .142(2) Uani d . 1 . O
 O3  .1320(2)  .21090(10)
 -.25160(10)
   .0634(6) Uani d . 1 . O
 O4  .0524(2)  .18320(10)
 -.15190(10)
   .0676(6) Uani d . 1 . O
 O5  -.0546(6)  .0927(4)  -.0577(4)  .107(2) Uani d P  .50 . O
 H51  -.0256  .1109  -.1023  .100 Uiso d P  .50 . H
 H52  -.1160  .1289  -.0448  .100 Uiso d P  .50 . H
 O5'  -.0579(5)  .1599(5)  -.0314(3)  .110(2) Uani d P  .50 . O
 H51'  -.0351  .1877  -.0733  .100 Uiso d P  .50 . H
 H52'  -.1131  .1888  -.0048  .100 Uiso d P  .50 . H
 O6  .1419(4)  .0551(3)  .0688(2)  .184(2) Uani d . 1 . O
 H61  .0732  .0748  .0227  .100 Uiso d . 1 . H
 H62  .1200  .0018  .0704  .100 Uiso d . 1 . H
 N1  .8224(2)  .24510(10)
 -.26540(10)
   .0443(5) Uani d . 1 . N
 H1A  .8963(2)  .22810(10)
  -.23080(10)
 .066 Uiso calc R 1 . H
 H1B  .7541(2)  .22970(10)
  -.24830(10)
 .066 Uiso calc R 1 . H
 N2  .3280(2)  .25800(10)
 -.31230(10)
   .0489(6) Uani d . 1 . N
 H2A  .2765(2)  .23680(10)
  -.28540(10)
 .073 Uiso calc R 1 . H
 H2B  .4115(2)  .24560(10)
  -.28710(10)
 .073 Uiso calc R 1 . H
 N3  .3765(2)  .17110(10)
 -.16980(10)
   .0442(5) Uani d . 1 . N
 C1  .8256(2)  .32760(10)
 -.2624(2)  .0467(6) Uani d . 1 . C
 H1  .7404(2)  .34630(10)
 -.2943(2)  .070 Uiso calc R 1 . H
 C2  .8445(3)  .3511(2)  -.1771(2)  .0682(9) Uani d . 1 . C
 H2C  .9263(3)  .3309(2)  -.1441(2)  .102 Uiso calc R 1 . H
 H2D  .7732(3)  .3318(2)  -.1581(2)  .102 Uiso calc R 1 . H
 C3  .8476(4)  .4351(2)  -.1703(2)  .0840(10)
  Uani d . 1 . C
 H3A  .7628(4)  .4549(2)  -.1993(2)  .126 Uiso calc R 1 . H
 H3B  .8639(4)  .4490(2)  -.1149(2)  .126 Uiso calc R 1 . H
 C4  .9538(4)  .4677(2)  -.2031(2)  .0790(10)
  Uani d . 1 . C
 H4A  .9499(4)  .5211(2)  -.2012(2)  .119 Uiso calc R 1 . H
 H4B 1.0395(4)  .4523(2)  -.1704(2)  .119 Uiso calc R 1 . H
 C5  .9367(3)  .4433(2)  -.2874(2)  .0713(9) Uani d . 1 . C
 H5A 1.0090(3)  .4621(2)  -.3058(2)  .107 Uiso calc R 1 . H
 H5B  .8558(3)  .4640(2)  -.3211(2)  .107 Uiso calc R 1 . H
 C6  .9320(3)  .3593(2)  -.2953(2)  .0589(8) Uani d . 1 . C
 H6A  .9148(3)  .3458(2)  -.3509(2)  .088 Uiso calc R 1 . H
 H6B 1.0165(3)  .3388(2)  -.2668(2)  .088 Uiso calc R 1 . H
 C7  .8110(2)  .21010(10)
 -.3444(2)  .0472(6) Uani d . 1 . C
 H7  .8878(2)  .22490(10)
 -.3618(2)  .071 Uiso calc R 1 . H
 C8  .8146(3)  .1276(2)  -.3351(2)  .0608(8) Uani d . 1 . C
 H8A  .7401(3)  .1115(2)  -.3172(2)  .091 Uiso calc R 1 . H
 H8B  .8945(3)  .1132(2)  -.2954(2)  .091 Uiso calc R 1 . H
 C9  .8099(4)  .0911(2)  -.4143(2)  .0780(10)
  Uani d . 1 . C
 H9A  .8881(4)  .1043(2)  -.4298(2)  .117 Uiso calc R 1 . H
 H9B  .8094(4)  .0379(2)  -.4081(2)  .117 Uiso calc R 1 . H
 C10  .6899(5)  .1142(2)  -.4784(2)  .0970(10)
   Uani d . 1 . C
 H10A  .6114(5)  .0969(2)  -.4656(2)  .145 Uiso calc R 1 . H
 H10B  .6919(5)  .0923(2)  -.5286(2)  .145 Uiso calc R 1 . H
 C11  .6852(5)  .1977(2)  -.4862(2)  .107(2) Uani d . 1 . C
 H11A  .6050(5)  .2121(2)  -.5257(2)  .160 Uiso calc R 1 . H
 H11B  .7592(5)  .2144(2)  -.5043(2)  .160 Uiso calc R 1 . H
 C12  .6901(3)  .2347(2)  -.4066(2)  .0713(9) Uani d . 1 . C
 H12A  .6912(3)  .2878(2)  -.4123(2)  .107 Uiso calc R 1 . H
 H12B  .6123(3)  .2215(2)  -.3905(2)  .107 Uiso calc R 1 . H
 C13  .3160(3)  .3395(2)  -.3050(2)  .0598(8) Uani d . 1 . C
 H13  .2237(3)  .3527(2)  -.3290(2)  .090 Uiso calc R 1 . H
 C14  .3492(4)  .3589(2)  -.2177(2)  .0850(10)
   Uani d . 1 . C
 H14A  .4388(4)  .3440(2)  -.1918(2)  .128 Uiso calc R 1 . H
 H14B  .2912(4)  .3322(2)  -.1932(2)  .128 Uiso calc R 1 . H
 C15  .3349(4)  .4416(2)  -.2057(3)  .1080(10)
   Uani d . 1 . C
 H15A  .2434(4)  .4557(2)  -.2265(3)  .161 Uiso calc R 1 . H
 H15B  .3619(4)  .4528(2)  -.1493(3)  .161 Uiso calc R 1 . H
 C16  .4154(5)  .4841(2)  -.2460(4)  .126(2) Uani d . 1 . C
 H16A  .5077(5)  .4745(2)  -.2207(4)  .190 Uiso calc R 1 . H
 H16B  .3998(5)  .5363(2)  -.2407(4)  .190 Uiso calc R 1 . H
 C17  .3848(7)  .4649(2)  -.3328(4)  .150(2) Uani d . 1 . C
 H17A  .4447(7)  .4914(2)  -.3561(4)  .225 Uiso calc R 1 . H
 H17B  .2962(7)  .4810(2)  -.3594(4)  .225 Uiso calc R 1 . H
 C18  .3964(5)  .3810(2)  -.3474(3)  .110(2) Uani d . 1 . C
 H18A  .3660(5)  .3706(2)  -.4039(3)  .166 Uiso calc R 1 . H
 H18B  .4877(5)  .3657(2)  -.3284(3)  .166 Uiso calc R 1 . H
 C19  .2950(3)  .2233(2)  -.3932(2)  .0538(7) Uani d . 1 . C
 H19  .3486(3)  .2463(2)  -.4242(2)  .081 Uiso calc R 1 . H
 C20  .3290(3)  .1424(2)  -.3829(2)  .0686(9) Uani d . 1 . C
 H20A  .2807(3)  .1198(2)  -.3493(2)  .103 Uiso calc R 1 . H
 H20B  .4222(3)  .1368(2)  -.3571(2)  .103 Uiso calc R 1 . H
 C21  .2946(4)  .1039(2)  -.4632(2)  .0890(10)
   Uani d . 1 . C
 H21A  .3484(4)  .1238(2)  -.4951(2)  .133 Uiso calc R 1 . H
 H21B  .3136(4)  .0517(2)  -.4555(2)  .133 Uiso calc R 1 . H
 C22  .1504(4)  .1145(2)  -.5065(2)  .0930(10)
   Uani d . 1 . C
 H22A  .1316(4)  .0917(2)  -.5586(2)  .139 Uiso calc R 1 . H
 H22B  .0967(4)  .0904(2)  -.4770(2)  .139 Uiso calc R 1 . H
 C23  .1161(4)  .1944(2)  -.5156(2)  .0920(10)
   Uani d . 1 . C
 H23A  .0226(4)  .1995(2)  -.5409(2)  .138 Uiso calc R 1 . H
 H23B  .1629(4)  .2171(2)  -.5499(2)  .138 Uiso calc R 1 . H
 C24  .1506(3)  .2342(2)  -.4363(2)  .0706(9) Uani d . 1 . C
 H24A  .0969(3)  .2153(2)  -.4039(2)  .106 Uiso calc R 1 . H
 H24B  .1323(3)  .2864(2)  -.4449(2)  .106 Uiso calc R 1 . H
 C25  .6069(3)  .1650(2)  -.1696(2)  .0653(9) Uani d . 1 . C
 C26  .4967(2)  .1459(2)  -.1330(2)  .0479(7) Uani d . 1 . C
 C27  .5216(3)  .1055(2)  -.0632(2)  .0556(7) Uani d . 1 . C
 H27  .6052(3)  .0869(2)  -.0396(2)  .083 Uiso calc R 1 . H
 C28  .4211(3)  .0934(2)  -.0294(2)  .0561(7) Uani d . 1 . C
 H28  .4361(3)  .0670(2)  .0178(2)  .084 Uiso calc R 1 . H
 C29  .2975(3)  .1207(2)  -.0660(2)  .0518(7) Uani d . 1 . C
 H29  .2286(3)  .1142(2)  -.0433(2)  .078 Uiso calc R 1 . H
 C30  .2782(2)  .15800(10)
  -.1372(2)  .0408(6) Uani d . 1 . C
 C31  .1433(2)  .1863(2)  -.1842(2)  .0455(6) Uani d . 1 . C
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
 O1  .0440(10)
  .084(2)  .0690(10)
  -.0080(10)
   .0210(10)
   .0070(10)
 O2  .0370(10)
  .235(4)  .155(3)  .035(2)  .028(2)  .093(3)
 O3  .0410(10)
  .088(2)  .0600(10)
  .0080(10)
  .0110(10)
  .0230(10)
 O4  .0400(10)
  .101(2)  .0660(10)
  .0050(10)
  .0210(10)
  .0050(10)
 O5  .083(4)  .127(5)  .117(5)  .022(4)  .039(3)  .052(4)
 O5'  .067(3)  .204(7)  .059(3)  -.022(4)  .019(2)  .024(4)
 O6  .146(3)  .249(5)  .133(3)  -.090(3)  -.002(2)  .047(3)
 N1  .0370(10)
  .0490(10)
  .0470(10)
  .0010(10)
  .0110(10)
  .0050(10)
 N2  .0450(10)
  .0520(10)
  .0490(10)
  .0030(10)
  .0110(10)
  .0110(10)
 N3  .0340(10)
  .0500(10)
  .0470(10)
  .0020(10)
  .0090(10)
  .0060(10)
 C1  .0390(10)
  .044(2)  .055(2)  .0030(10)
  .0100(10)
  .0010(10)
 C2  .077(2)  .072(2)  .063(2)  -.009(2)  .032(2)  -.012(2)
 C3  .103(3)  .072(2)  .086(3)  -.008(2)  .041(2)  -.023(2)
 C4  .084(2)  .057(2)  .093(3)  -.013(2)  .018(2)  -.016(2)
 C5  .077(2)  .051(2)  .084(2)  -.011(2)  .019(2)  .005(2)
 C6  .066(2)  .053(2)  .065(2)  -.0070(10)
   .030(2)  .0000(10)
 C7  .0420(10)
  .048(2)  .052(2)  -.0050(10)
   .0130(10)
   -.0010(10)
 C8  .061(2)  .050(2)  .068(2)  .0030(10)
  .013(2)  .000(2)
 C9  .087(3)  .059(2)  .093(3)  -.008(2)  .033(2)  -.018(2)
 C10  .125(4)  .081(3)  .071(2)  -.010(2)  .005(2)  -.023(2)
 C11  .156(4)  .083(3)  .059(2)  .007(3)  -.006(2)  -.006(2)
 C12  .078(2)  .062(2)  .059(2)  .007(2)  -.006(2)  .002(2)
 C13  .052(2)  .050(2)  .073(2)  .0030(10)
   .011(2)  .007(2)
 C14  .099(3)  .064(2)  .087(3)  -.016(2)  .015(2)  -.018(2)
 C15  .094(3)  .083(3)  .139(4)  -.017(2)  .021(3)  -.034(3)
 C16  .097(3)  .069(3)  .210(6)  -.004(2)  .036(4)  -.017(3)
 C17  .222(6)  .052(3)  .213(6)  .014(3)  .122(6)  .042(3)
 C18  .140(4)  .060(2)  .162(4)  .006(2)  .093(4)  .029(2)
 C19  .058(2)  .060(2)  .044(2)  .0110(10)
   .0140(10)
   .0080(10)
 C20  .068(2)  .067(2)  .062(2)  .017(2)  .004(2)  .001(2)
 C21  .091(3)  .087(3)  .079(2)  .027(2)  .008(2)  -.020(2)
 C22  .087(3)  .104(3)  .076(2)  .011(2)  .003(2)  -.027(2)
 C23  .087(3)  .120(3)  .053(2)  .038(2)  -.004(2)  -.012(2)
 C24  .066(2)  .087(2)  .051(2)  .025(2)  .003(2)  -.002(2)
 C25  .037(2)  .088(2)  .068(2)  -.003(2)  .010(2)  .013(2)
 C26  .0360(10)
   .054(2)  .051(2)  .0010(10)
   .0080(10)
   .0020(10)
 C27  .045(2)  .058(2)  .055(2)  .0070(10)
   .0010(10)
   .0080(10)
 C28  .065(2)  .051(2)  .050(2)  .0030(10)
   .013(2)  .0120(10)
 C29  .052(2)  .050(2)  .054(2)  -.0020(10)
 .0180(10)
 .0030(10)
 C30  .0390(10)
   .041(2)  .0440(10)
   -.0030(10)
 .0120(10) .0000(10)
 C31  .0340(10)
   .051(2)  .051(2)  -.0020(10)
 .0110(10)
 -.0030(10)
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
 O1 C25 . 1.246(4) yes
 O2 C25 . 1.217(4) yes
 O3 C31 . 1.235(3) yes
 O4 C31 . 1.245(3) yes
 N1 C1 . 1.499(3) yes
 N1 C7 . 1.496(3) yes
 N2 C13 . 1.493(3) yes
 N2 C19 . 1.499(3) yes
 N3 C26 . 1.337(3) yes
 N3 C30 . 1.339(3) yes
 C1 C2 . 1.511(4) ?
 C1 C6 . 1.513(4) ?
 C2 C3 . 1.528(4) ?
 C3 C4 . 1.516(5) ?
 C4 C5 . 1.503(4) ?
 C5 C6 . 1.529(4) ?
 C7 C8 . 1.505(4) ?
 C7 C12 . 1.500(4) ?
 C8 C9 . 1.524(4) ?
 C9 C10 . 1.504(5) ?
 C10 C11 . 1.519(5) ?
 C11 C12 . 1.536(5) ?
 C13 C14 . 1.511(5) ?
 C13 C18 . 1.481(5) ?
 C14 C15 . 1.527(5) ?
 C15 C16 . 1.467(6) ?
 C16 C17 . 1.504(7) ?
 C17 C18 . 1.553(6) ?
 C19 C20 . 1.508(4) ?
 C19 C24 . 1.518(4) ?
 C20 C21 . 1.521(4) ?
 C21 C22 . 1.517(5) ?
 C22 C23 . 1.491(5) ?
 C23 C24 . 1.517(4) ?
 C25 C26 . 1.518(4) ?
 C26 C27 . 1.386(4) ?
 C27 C28 . 1.368(4) ?
 C28 C29 . 1.380(4) ?
 C29 C30 . 1.382(4) ?
 C30 C31 . 1.526(3) ?
 N1 O1 . 2.871(3) yes
 N1 O4 1_655 2.908(3) yes
 N2 O1 . 2.846(3) yes
 N2 O3 . 2.717(3) yes
 O5 O2 1_455 2.602(6) yes
 O5 O4 . 2.778(6) yes
 O5 O6 . 2.674(7) yes
 O5' O2 1_455 2.656(6) yes
 O5' O4 . 2.710(5) yes
 O6 O5 3_555 2.825(9) yes