#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012163.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_2012163
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  955
_journal_page_last  957
_publ_section_title
;
Hydrogen-bonded bilayers in piperazinium(2+) bis(mandelate)
bis(methanol) solvate
;
loop_
_publ_author_name
  'Farrell, Dorcas M. M.'
  'Ferguson, George'
  'Lough, Alan J.'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C4 H12 N2 2+ , 2C8 H7 O3 - , 2C H4 O'
_chemical_formula_sum  'C22 H34 N2 O8'
_chemical_formula_weight  454.51
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, y, -z-1/2'
  '-x-1/2, y-1/2, z'
  'x, -y-1/2, z-1/2'
_cell_length_a  7.7360(2)
_cell_length_b  10.2394(4)
_cell_length_c  29.7822(11)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  2359.11(14)
_cell_formula_units_Z  4
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.280
_diffrn_ambient_temperature  150(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
  O1  .8595(2)  .46050(17)  .59125(5)  .0443(5) Uani d . 1 . . O
  O2  .8795(3)  .28474(17)  .54799(6)  .0587(6) Uani d . 1 . . O
  O3 1.1657(3)  .20571(17)  .58472(5)  .0471(6) Uani d . 1 . . O
  H3 1.2532  .1815  .5992  .071 Uiso calc R 1 . . H
  C11 1.0100(3)  .2564(2)  .65444(7)  .0352(7) Uani d . 1 . . C
  C12  .9594(4)  .1274(3)  .66031(8)  .0427(7) Uani d . 1 . . C
  H12  .9713  .0672  .6362  .051 Uiso calc R 1 . . H
  C13  .8919(4)  .0858(3)  .70081(9)  .0495(8) Uani d . 1 . . C
  H13  .8595  -.0031  .7045  .059 Uiso calc R 1 . . H
  C14  .8713(4)  .1718(3)  .73593(9)  .0481(8) Uani d . 1 . . C
  H14  .8242  .1430  .7637  .058 Uiso calc R 1 . . H
  C15  .9201(4)  .3004(3)  .73029(8)  .0467(8) Uani d . 1 . . C
  H15  .9057  .3606  .7543  .056 Uiso calc R 1 . . H
  C16  .9894(4)  .3423(3)  .69026(8)  .0423(7) Uani d . 1 . . C
  H16 1.0237  .4309  .6870  .051 Uiso calc R 1 . . H
  C17 1.0770(3)  .3043(2)  .60933(7)  .0362(7) Uani d . 1 . . C
  H17 1.1586  .3784  .6148  .043 Uiso calc R 1 . . H
  C18  .9281(4)  .3538(3)  .58021(8)  .0366(7) Uani d . 1 . . C
  N1A  .6078(5)  .5241(4)  .53836(11)  .0366(11) Uani d PD  .50 . 1 N
  H1A  .5691  .6049  .5474  .044 Uiso calc PR  .50 . 1 H
  H2A  .6952  .4990  .5575  .044 Uiso calc PR  .50 . 1 H
  C2A  .4644(14)  .4290(12)  .5413(5)  .0369(11) Uani d PD  .50 A 1 C
  H2A1  .5077  .3402  .5345  .044 Uiso calc PR  .50 A 1 H
  H2A2  .4165  .4286  .5721  .044 Uiso calc PR  .50 A 1 H
  C3A  .324(2)  .4665(10)  .5079(3)  .0384(10) Uani d PD  .50 . 1 C
  H3A1  .2304  .4003  .5088  .046 Uiso calc PR  .50 . 1 H
  H3A2  .2731  .5516  .5167  .046 Uiso calc PR  .50 . 1 H
  N1B  .6120(5)  .3897(4)  .50377(12)  .0361(11) Uani d PD  .50 . 2 N
  H1B  .6984  .3450  .5184  .043 Uiso calc PR  .50 . 2 H
  H2B  .5766  .3396  .4798  .043 Uiso calc PR  .50 . 2 H
  C2B  .4650(14)  .4083(13)  .5348(5)  .0369(11) Uani d PD  .50 B 2 C
  H2B1  .4211  .3219  .5444  .044 Uiso calc PR  .50 B 2 H
  H2B2  .5054  .4553  .5619  .044 Uiso calc PR  .50 B 2 H
  C3B  .318(2)  .4853(8)  .5132(3)  .0384(10) Uani d PD  .50 . 2 C
  H3B1  .2675  .4345  .4881  .046 Uiso calc PR  .50 . 2 H
  H3B2  .2262  .5021  .5356  .046 Uiso calc PR  .50 . 2 H
  O4 1.0545(3)  .64236(19)  .63172(7)  .0625(6) Uani d . 1 . . O
  H31  .9826  .5963  .6178  .094 Uiso calc R 1 . . H
  C4  .9711(4)  .7525(3)  .64941(8)  .0468(8) Uani d . 1 . . C
  H41  .9040  .7272  .6759  .070 Uiso calc R 1 . . H
  H42  .8934  .7895  .6267  .070 Uiso calc R 1 . . H
  H43 1.0575  .8180  .6580  .070 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
  O1  .0443(13)  .0341(11)  .0544(11)  .0059(10)  -.0040(9)  -.0032(8)
  O2  .0784(16)  .0412(12)  .0566(12)  .0075(11)  -.0323(11)  -.0092(10)
  O3  .0503(14)  .0470(12)  .0441(10)  .0140(10)  -.0044(9)  -.0092(9)
  C11  .0315(17)  .0349(16)  .0392(14)  .0028(13)  -.0071(12)  .0007(12)
  C12  .046(2)  .0350(17)  .0473(17)  .0031(14)  -.0044(14)  -.0034(13)
  C13  .052(2)  .0401(17)  .0565(18)  .0001(16)  -.0028(15)  .0092(15)
  C14  .0462(19)  .054(2)  .0438(16)  .0054(16)  -.0046(13)  .0100(14)
  C15  .054(2)  .0503(19)  .0362(16)  .0061(16)  -.0046(14)  -.0020(13)
  C16  .052(2)  .0345(16)  .0408(16)  .0011(14)  -.0093(14)  -.0024(12)
  C17  .0360(17)  .0335(15)  .0391(14)  -.0004(14)  -.0034(12)  -.0057(12)
  C18  .0438(19)  .0323(15)  .0337(15)  -.0032(14)  -.0007(13)  .0022(12)
  N1A  .041(3)  .037(2)  .032(2)  .008(2)  -.0099(19)  -.0055(18)
  C2A  .0422(19)  .040(3)  .029(3)  -.006(2)  -.0017(18)  -.0043(19)
  C3A  .041(2)  .037(3)  .037(2)  .001(2)  -.001(2)  -.0002(17)
  N1B  .039(3)  .035(3)  .034(2)  .007(2)  -.0081(19)  -.0022(18)
  C2B  .0422(19)  .040(3)  .029(3)  -.006(2)  -.0017(18)  -.0043(19)
  C3B  .041(2)  .037(3)  .037(2)  .001(2)  -.001(2)  -.0002(17)
  O4  .0443(14)  .0442(12)  .0990(16)  -.0069(10)  .0116(12)  -.0199(11)
  C4  .046(2)  .0452(17)  .0492(15)  -.0015(15)  .0054(14)  -.0022(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
  O1 C18 . 1.258(3) ?
  O2 C18 . 1.250(3) ?
  O3 C17 . 1.424(3) ?
  O3 H3 .  .84 ?
  C11 C12 . 1.389(3) ?
  C11 C16 . 1.392(3) ?
  C11 C17 . 1.521(3) ?
  C12 C13 . 1.382(3) ?
  C12 H12 .  .95 ?
  C13 C14 . 1.377(4) ?
  C13 H13 .  .95 ?
  C14 C15 . 1.380(4) ?
  C14 H14 .  .95 ?
  C15 C16 . 1.376(3) ?
  C15 H15 .  .95 ?
  C16 H16 .  .95 ?
  C17 C18 . 1.528(4) ?
  C17 H17 . 1.00 ?
  N1A C3A 5_666 1.479(3) ?
  N1A C2A . 1.478(3) ?
  N1A H1A .  .92 ?
  N1A H2A .  .92 ?
  C2A C3A . 1.525(3) ?
  C2A H2A1 .  .99 ?
  C2A H2A2 .  .99 ?
  C3A N1A 5_666 1.479(3) ?
  C3A H3A1 .  .99 ?
  C3A H3A2 .  .99 ?
  N1B C3B 5_666 1.479(3) ?
  N1B C2B . 1.478(3) ?
  N1B H1B .  .92 ?
  N1B H2B .  .92 ?
  C2B C3B . 1.525(3) ?
  C2B H2B1 .  .99 ?
  C2B H2B2 .  .99 ?
  C3B N1B 5_666 1.478(3) ?
  C3B H3B1 .  .99 ?
  C3B H3B2 .  .99 ?
  O4 C4 . 1.402(3) ?
  O4 H31 .  .84 ?
  C4 H41 .  .98 ?
  C4 H42 .  .98 ?
  C4 H43 .  .98 ?
_cod_database_code 2012163