#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012902.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_2012902
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o499
_journal_page_last  o502
_publ_section_title
;
Hydrogen bonding in 2-(hydroxymethyl)-1,3-propanediol and
N,N'-bis[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]malonamide
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
loop_
_publ_author_name
  'Fernandes, Christiane'
  'Wardell, James L.'
  'Skakle, Janet M. S.'
_chemical_formula_moiety  'C11 H22 N2 O8'
_chemical_formula_sum  'C11 H22 N2 O8'
_chemical_formula_iupac  'C11 H22 N2 O8'
_chemical_formula_weight  310.31
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  11.6928(11)
_cell_length_b  5.6610(5)
_cell_length_c  21.0034(19)
_cell_angle_alpha  90.00
_cell_angle_beta  92.700(2)
_cell_angle_gamma  90.00
_cell_volume  1388.7(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  292(2)
_exptl_crystal_density_diffrn  1.484
_diffrn_ambient_temperature  292(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 0.18283(10) 0.0069(2) 0.37960(5) 0.0214(2) Uani d . 1 . . C
  C2 0.30828(11) 0.0892(2) 0.39066(6) 0.0273(3) Uani d . 1 . . C
  H2A 0.3471 0.0772 0.3510 0.033 Uiso calc R 1 . . H
  H2B 0.3092 0.2537 0.4035 0.033 Uiso calc R 1 . . H
  O2 0.36882(10) -0.0482(2) 0.43840(6) 0.0388(3) Uani d . 1 . . O
  H2 0.3746 0.0272 0.4717 0.058 Uiso calc R 1 . . H
  C3 0.17427(12) -0.2557(2) 0.36034(7) 0.0284(3) Uani d . 1 . . C
  H3A 0.2077 -0.3511 0.3948 0.034 Uiso calc R 1 . . H
  H3B 0.0941 -0.2984 0.3548 0.034 Uiso calc R 1 . . H
  O3 0.22973(10) -0.3107(2) 0.30335(5) 0.0345(3) Uani d . 1 . . O
  H3 0.2950 -0.3568 0.3123 0.052 Uiso calc R 1 . . H
  C4 0.11605(13) 0.0373(2) 0.44108(6) 0.0293(3) Uani d . 1 . . C
  H4A 0.0442 -0.0478 0.4363 0.035 Uiso calc R 1 . . H
  H4B 0.1601 -0.0320 0.4766 0.035 Uiso calc R 1 . . H
  O4 0.09299(10) 0.2793(2) 0.45517(5) 0.0353(3) Uani d . 1 . . O
  H4 0.0298 0.3157 0.4396 0.053 Uiso calc R 1 . . H
  N1 0.13697(9) 0.15798(19) 0.32724(5) 0.0230(2) Uani d . 1 . . N
  H1 0.1850 0.2435 0.3078 0.028 Uiso calc R 1 . . H
  C5 0.02636(11) 0.1730(2) 0.30746(6) 0.0234(2) Uani d . 1 . . C
  O1 -0.05086(9) 0.0641(2) 0.33328(6) 0.0406(3) Uani d . 1 . . O
  C6 0.0000 0.3319(3) 0.2500 0.0246(3) Uani d S 1 . . C
  H6A -0.0696(18) 0.428(4) 0.2556(10) 0.034(5) Uiso 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
  C1 0.0242(5) 0.0226(5) 0.0172(5) 0.0016(4) -0.0019(4) 0.0007(3)
  C2 0.0242(6) 0.0303(6) 0.0267(5) 0.0010(4) -0.0059(4) -0.0027(4)
  O2 0.0393(6) 0.0394(6) 0.0361(5) 0.0150(5) -0.0149(5) -0.0085(4)
  C3 0.0305(6) 0.0237(5) 0.0311(6) -0.0004(4) 0.0032(5) -0.0017(4)
  O3 0.0322(5) 0.0374(5) 0.0340(5) 0.0045(4) 0.0018(4) -0.0111(4)
  C4 0.0347(7) 0.0326(6) 0.0210(5) 0.0055(5) 0.0046(5) 0.0034(4)
  O4 0.0385(6) 0.0400(6) 0.0271(5) 0.0120(4) -0.0025(4) -0.0089(4)
  N1 0.0221(5) 0.0256(5) 0.0211(4) -0.0014(3) 0.0000(3) 0.0040(3)
  C5 0.0234(5) 0.0263(5) 0.0206(5) 0.0008(4) 0.0003(4) 0.0002(4)
  O1 0.0242(5) 0.0584(7) 0.0392(6) -0.0039(5) 0.0014(4) 0.0191(5)
  C6 0.0294(8) 0.0255(7) 0.0184(6) 0.000 -0.0054(6) 0.000
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 N1 . 1.4740(15) ?
  C1 C3 . 1.5429(17) ?
  C1 C2 . 1.5460(18) ?
  C1 C4 . 1.5496(17) ?
  C2 O2 . 1.4299(16) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  O2 H2 . 0.8200 ?
  C3 O3 . 1.4224(17) ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  O3 H3 . 0.8200 ?
  C4 O4 . 1.4301(17) ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  O4 H4 . 0.8200 ?
  N1 C5 . 1.3424(16) ?
  N1 H1 . 0.8600 ?
  C5 O1 . 1.2392(16) ?
  C5 C6 . 1.5251(16) ?
  C6 C5 2 1.5250(16) ?
  C6 H6A . 0.99(2) ?
_cod_database_code 2012902