#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2011714.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_2011714
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  92
_journal_page_last  94
_publ_section_title
;
A three-dimensional hydrogen-bonded framework in
4,4'-trimethylenedipiperidinium--2,5-dicarboxybenzene-1,4-dicarboxylate--water
 (1/1/1)
;
loop_
_publ_author_name
  'Burchell, Colin J.'
  'Ferguson, George'
  'Lough, Alan J.'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C13 H28 N2 2+ , C10 H4 O8 2- , H2 O'
_chemical_formula_sum  'C23 H34 N2 O9'
_chemical_formula_weight  482.52
_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  10.5885(4)
_cell_length_b  11.5840(6)
_cell_length_c  11.8301(6)
_cell_angle_alpha  61.453(2)
_cell_angle_beta  80.999(3)
_cell_angle_gamma  64.055(3)
_cell_volume  1143.63(9)
_cell_formula_units_Z  2
_cell_measurement_temperature  150.0(10)
_exptl_crystal_density_diffrn  1.401
_diffrn_ambient_temperature  150.0(10)
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
  O1  .82375(10)  .64403(13)  .90569(12)  .0376(3) Uani d . 1 . . O
  O2  .68001(11)  .79086(13)  .98085(11)  .0343(3) Uani d . 1 . . O
  O3  .44084(11)  .87211(13) 1.03762(11)  .0331(3) Uani d . 1 . . O
  H3  .5587  .8354 1.0043  .050 Uiso calc R 1 . . H
  O4  .26730(10)  .80737(13) 1.06721(10)  .0303(2) Uani d . 1 . . O
  O5  .14771(11)  .67892(15)  .80144(13)  .0449(3) Uani d . 1 . . O
  O6  .30076(11)  .50765(13)  .75328(12)  .0382(3) Uani d . 1 . . O
  O7  .53272(11)  .44656(12)  .68017(11)  .0330(3) Uani d . 1 . . O
  H7  .4199  .4727  .7242  .049 Uiso calc R 1 . . H
  O8  .69639(11)  .52896(12)  .63499(10)  .0309(3) Uani d . 1 . . O
  C11  .58191(13)  .69456(14)  .89256(12)  .0182(3) Uani d . 1 . . C
  C12  .44423(14)  .73143(15)  .93550(12)  .0190(3) Uani d . 1 . . C
  C13  .35288(14)  .69758(15)  .89673(12)  .0206(3) Uani d . 1 . . C
  H13  .2602  .7225  .9254  .025 Uiso calc R 1 . . H
  C14  .38860(14)  .62966(15)  .81884(12)  .0194(3) Uani d . 1 . . C
  C15  .52497(13)  .59507(14)  .77408(12)  .0189(3) Uani d . 1 . . C
  C16  .61582(14)  .63032(14)  .81167(13)  .0194(3) Uani d . 1 . . C
  H16  .7071  .6091  .7799  .023 Uiso calc R 1 . . H
  C17  .70384(14)  .70970(15)  .92861(13)  .0220(3) Uani d . 1 . . C
  C18  .37939(14)  .80657(16) 1.01991(13)  .0228(3) Uani d . 1 . . C
  C19  .26865(15)  .60609(17)  .78939(14)  .0259(3) Uani d . 1 . . C
  C110  .58958(14)  .51981(15)  .68957(13)  .0222(3) Uani d . 1 . . C
  N21  .27499(12)  .87121(14)  .27730(11)  .0246(3) Uani d . 1 . . N
  H21A  .2590  .7929  .3442  .030 Uiso calc R 1 . . H
  H21B  .2780  .8650  .2005  .030 Uiso calc R 1 . . H
  N31  .02798(12) 1.42914(14)  .84862(12)  .0256(3) Uani d . 1 . . N
  H31A  -.0324 1.5047  .8680  .031 Uiso calc R 1 . . H
  H31B  .1198 1.3980  .8790  .031 Uiso calc R 1 . . H
  C22  .15624(15) 1.00982(17)  .26397(14)  .0257(3) Uani d . 1 . . C
  H22A  .0664 1.0129  .2459  .031 Uiso calc R 1 . . H
  H22B  .1700 1.0926  .1908  .031 Uiso calc R 1 . . H
  C23  .14959(15) 1.02207(17)  .38747(14)  .0254(3) Uani d . 1 . . C
  H23A  .1235  .9463  .4577  .030 Uiso calc R 1 . . H
  H23B  .0748 1.1172  .3747  .030 Uiso calc R 1 . . H
  C24  .28887(14) 1.00635(16)  .42863(13)  .0225(3) Uani d . 1 . . C
  H24  .3074 1.0917  .3641  .027 Uiso calc R 1 . . H
  C25  .40838(15)  .86854(16)  .43099(14)  .0256(3) Uani d . 1 . . C
  H25A  .4993  .8639  .4486  .031 Uiso calc R 1 . . H
  H25B  .3968  .7833  .5024  .031 Uiso calc R 1 . . H
  C26  .41294(15)  .86098(17)  .30566(14)  .0265(3) Uani d . 1 . . C
  H26A  .4319  .9415  .2344  .032 Uiso calc R 1 . . H
  H26B  .4894  .7687  .3134  .032 Uiso calc R 1 . . H
  C32  -.01515(15) 1.30647(17)  .91628(14)  .0272(3) Uani d . 1 . . C
  H32A  -.1140 1.3402  .8888  .033 Uiso calc R 1 . . H
  H32B  -.0092 1.2715 1.0106  .033 Uiso calc R 1 . . H
  C33  .07980(15) 1.18368(16)  .88507(13)  .0253(3) Uani d . 1 . . C
  H33A  .0456 1.1065  .9256  .030 Uiso calc R 1 . . H
  H33B  .1763 1.1423  .9226  .030 Uiso calc R 1 . . H
  C34  .08470(14) 1.23283(15)  .73985(13)  .0207(3) Uani d . 1 . . C
  H34  -.0113 1.2641  .7051  .025 Uiso calc R 1 . . H
  C35  .12204(15) 1.36314(16)  .67410(14)  .0243(3) Uani d . 1 . . C
  H35A  .2199 1.3321  .7020  .029 Uiso calc R 1 . . H
  H35B  .1170 1.3997  .5795  .029 Uiso calc R 1 . . H
  C36  .02358(14) 1.48433(16)  .70614(13)  .0237(3) Uani d . 1 . . C
  H36A  .0526 1.5653  .6645  .028 Uiso calc R 1 . . H
  H36B  -.0736 1.5209  .6729  .028 Uiso calc R 1 . . H
  C4  .28495(16)  .99856(16)  .56186(14)  .0268(3) Uani d . 1 . . C
  H4A  .2575  .9196  .6232  .032 Uiso calc R 1 . . H
  H4B  .3816  .9713  .5898  .032 Uiso calc R 1 . . H
  C5  .18704(16) 1.13499(16)  .57331(14)  .0264(3) Uani d . 1 . . C
  H5A  .0902 1.1667  .5423  .032 Uiso calc R 1 . . H
  H5B  .2177 1.2133  .5184  .032 Uiso calc R 1 . . H
  C6  .18756(15) 1.10743(16)  .71347(14)  .0250(3) Uani d . 1 . . C
  H6A  .1660 1.0225  .7680  .030 Uiso calc R 1 . . H
  H6B  .2839 1.0818  .7409  .030 Uiso calc R 1 . . H
  O9  .20536(12)  .65392(13)  .47598(11)  .0308(3) Uani d D 1 . . O
  H91  .238(2)  .612(2)  .5572(8)  .076(8) Uiso d D 1 . . H
  H92  .243(2)  .5873(16)  .4483(19)  .057(6) Uiso d D 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
  O1  .0200(5)  .0430(7)  .0652(8)  -.0083(5)  -.0002(5)  -.0397(7)
  O2  .0338(6)  .0505(8)  .0449(7)  -.0249(6)  .0119(5)  -.0375(6)
  O3  .0357(6)  .0433(7)  .0410(6)  -.0210(5)  .0128(5)  -.0335(6)
  O4  .0271(5)  .0418(7)  .0295(6)  -.0145(5)  .0085(4)  -.0239(5)
  O5  .0241(6)  .0724(10)  .0641(8)  -.0214(6)  .0099(5)  -.0515(8)
  O6  .0285(6)  .0431(7)  .0629(8)  -.0166(5)  .0012(5)  -.0370(7)
  O7  .0323(6)  .0353(7)  .0466(7)  -.0144(5)  .0019(5)  -.0297(6)
  O8  .0315(6)  .0396(7)  .0352(6)  -.0172(5)  .0105(5)  -.0275(5)
  C11  .0213(6)  .0165(6)  .0166(6)  -.0077(5)  -.0007(5)  -.0071(5)
  C12  .0228(6)  .0180(7)  .0149(6)  -.0079(5)  .0012(5)  -.0071(5)
  C13  .0206(6)  .0226(7)  .0171(6)  -.0092(5)  .0021(5)  -.0082(6)
  C14  .0220(6)  .0188(7)  .0165(6)  -.0091(5)  -.0006(5)  -.0065(5)
  C15  .0220(6)  .0161(7)  .0172(6)  -.0065(5)  -.0015(5)  -.0072(5)
  C16  .0187(6)  .0189(7)  .0205(6)  -.0064(5)  .0006(5)  -.0100(6)
  C17  .0242(7)  .0217(7)  .0226(7)  -.0099(6)  -.0011(5)  -.0110(6)
  C18  .0265(7)  .0244(8)  .0175(6)  -.0085(6)  .0014(5)  -.0117(6)
  C19  .0256(7)  .0330(8)  .0252(7)  -.0154(6)  .0015(6)  -.0151(7)
  C110  .0245(7)  .0203(7)  .0228(7)  -.0058(5)  -.0031(5)  -.0124(6)
  N21  .0302(6)  .0286(7)  .0227(6)  -.0145(5)  .0056(5)  -.0165(5)
  N31  .0237(6)  .0273(7)  .0297(6)  -.0055(5)  -.0017(5)  -.0196(6)
  C22  .0269(7)  .0282(8)  .0240(7)  -.0106(6)  .0002(6)  -.0138(6)
  C23  .0259(7)  .0268(8)  .0255(7)  -.0085(6)  .0029(6)  -.0162(6)
  C24  .0262(7)  .0217(7)  .0216(7)  -.0083(6)  .0013(5)  -.0128(6)
  C25  .0247(7)  .0258(8)  .0279(7)  -.0065(6)  -.0005(6)  -.0166(6)
  C26  .0255(7)  .0292(8)  .0307(8)  -.0108(6)  .0056(6)  -.0197(7)
  C32  .0286(7)  .0278(8)  .0222(7)  -.0080(6)  .0030(6)  -.0132(6)
  C33  .0294(7)  .0252(8)  .0217(7)  -.0106(6)  .0020(6)  -.0119(6)
  C34  .0209(6)  .0219(7)  .0214(6)  -.0073(5)  .0001(5)  -.0125(6)
  C35  .0253(7)  .0255(8)  .0251(7)  -.0107(6)  .0057(6)  -.0148(6)
  C36  .0236(7)  .0230(7)  .0264(7)  -.0098(6)  .0024(5)  -.0129(6)
  C4  .0329(8)  .0220(8)  .0236(7)  -.0051(6)  -.0030(6)  -.0135(6)
  C5  .0321(7)  .0227(8)  .0233(7)  -.0065(6)  -.0009(6)  -.0135(6)
  C6  .0294(7)  .0225(7)  .0232(7)  -.0068(6)  -.0019(6)  -.0131(6)
  O9  .0391(6)  .0316(7)  .0284(6)  -.0166(5)  .0081(5)  -.0188(5)
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 C17 . 1.2283(17) y
  O2 C17 . 1.2761(17) y
  O3 C18 . 1.2926(17) y
  O3 H3 . 1.20 ?
  O4 C18 . 1.2286(17) y
  O5 C19 . 1.2184(18) y
  O6 C19 . 1.2958(18) y
  O7 C110 . 1.2857(17) y
  O7 H7 . 1.20 ?
  O8 C110 . 1.2321(17) y
  C11 C16 . 1.3920(18) ?
  C11 C12 . 1.4129(18) ?
  C11 C17 . 1.5237(18) ?
  C12 C13 . 1.3936(19) ?
  C12 C18 . 1.5230(19) ?
  C13 C14 . 1.3908(19) ?
  C13 H13 .  .95 ?
  C14 C15 . 1.4083(18) ?
  C14 C19 . 1.5304(18) ?
  C15 C16 . 1.3933(18) ?
  C15 C110 . 1.5247(19) ?
  C16 H16 .  .95 ?
  N21 C22 . 1.4958(19) y
  N21 C26 . 1.4913(18) y
  N21 H21A .  .94 ?
  N21 H21B .  .94 ?
  N31 C32 . 1.4950(19) y
  N31 C36 . 1.4902(18) y
  N31 H31A .  .94 ?
  N31 H31B .  .94 ?
  C22 C23 . 1.5221(19) ?
  C22 H22A .  .99 ?
  C22 H22B .  .99 ?
  C23 C24 . 1.5330(19) ?
  C23 H23A .  .99 ?
  C23 H23B .  .99 ?
  C24 C4 . 1.5300(19) ?
  C24 C25 . 1.5334(19) ?
  C24 H24 . 1.00 ?
  C25 C26 . 1.519(2) ?
  C25 H25A .  .99 ?
  C25 H25B .  .99 ?
  C26 H26A .  .99 ?
  C26 H26B .  .99 ?
  C32 C33 . 1.518(2) ?
  C32 H32A .  .99 ?
  C32 H32B .  .99 ?
  C33 C34 . 1.5302(19) ?
  C33 H33A .  .99 ?
  C33 H33B .  .99 ?
  C34 C6 . 1.5285(19) ?
  C34 C35 . 1.5309(19) ?
  C34 H34 . 1.00 ?
  C35 C36 . 1.5185(19) ?
  C35 H35A .  .99 ?
  C35 H35B .  .99 ?
  C36 H36A .  .99 ?
  C36 H36B .  .99 ?
  C4 C5 . 1.522(2) ?
  C4 H4A .  .99 ?
  C4 H4B .  .99 ?
  C5 C6 . 1.5319(19) ?
  C5 H5A .  .99 ?
  C5 H5B .  .99 ?
  C6 H6A .  .99 ?
  C6 H6B .  .99 ?
  O9 H91 .  .89 ?
  O9 H92 .  .89 ?