#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/46/2004638.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2004638
loop_
_publ_author_name
'Barnes, H. A.'
'Barnes, J. C.'
_publ_section_title
;
 Hydrogen Bonding in 2-Methyl-1,2,3-propanetricarboxylic Acid, Ammonium
 Dihydrogen 1,2,3-Propanetricarboxylate Hemihydrate and Tetraammonium
 1,2,3,4-Butanetetracarboxylate Monohydrate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              731
_journal_page_last               736
_journal_paper_doi               10.1107/S0108270195013527
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'N H4 1+, C6 H7 O6 1-, 1/2H2 O1'
_chemical_formula_structural     C~3~H~5~(COOH)~2~(COO^-^).NH~4~^+^.0.5H~2~O
_chemical_formula_sum            'C6 H12 N O6.5'
_chemical_formula_weight         202.17
_chemical_name_common            'ammonium tricarballylate hydrate (1:1:0.5)'
_chemical_name_systematic
;
propane-1,2,3-tricarboxylic acid, mono-ammonium salt hemi-hydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 93.565(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.9331(12)
_cell_length_b                   7.8035(14)
_cell_length_c                   7.4103(3)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1785.3(3)
_computing_cell_refinement       MADNES
_computing_data_collection       'MADNES (Pflugrath & Messerschmidt, 1991)'
_computing_data_reduction        MADNES
_computing_molecular_graphics
'PLATON92 (Spek, 1992a) and PLUTON92 (Spek, 1992b)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measurement_device       'Enraf-Nonius CAD-4 FAST'
_diffrn_measurement_method       'Measurement method: area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3797
_diffrn_reflns_theta_max         24.72
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.889
_refine_ls_goodness_of_fit_obs   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_restrained_S_obs      1.038
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_obs          0.040
_refine_ls_shift/esd_max         0.09
_refine_ls_shift/esd_mean        0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0437P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.100
_refine_ls_wR_factor_obs         0.0866
_reflns_number_observed          975
_reflns_number_total             1386
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            li1138.cif
_cod_data_source_block           aca
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C6 H12 N O6.50'
_cod_database_code               2004638
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'
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 0.0316(13) 0.0253(14) 0.0258(13) -0.0052(11) 0.0019(10) -0.0006(12)
C2 0.0236(12) 0.0258(13) 0.0185(11) -0.0050(10) 0.0021(9) 0.0001(11)
C3 0.0261(13) 0.042(2) 0.0209(12) -0.0016(13) 0.0022(10) -0.0016(12)
C4 0.0309(12) 0.0247(14) 0.0217(12) 0.0022(11) 0.0040(9) -0.0034(11)
O5 0.0378(10) 0.0300(10) 0.0504(10) 0.0061(8) 0.0019(7) 0.0147(9)
O6 0.0280(9) 0.0265(9) 0.0304(9) -0.0029(7) -0.0009(7) 0.0052(7)
C7 0.0242(12) 0.0244(13) 0.0215(11) -0.0016(10) 0.0006(10) 0.0034(10)
O8 0.0288(9) 0.0464(11) 0.0225(8) -0.0063(7) -0.0032(6) -0.0025(7)
O9 0.0299(9) 0.0590(12) 0.0190(8) -0.0100(8) 0.0037(7) -0.0021(8)
C10 0.0232(12) 0.0380(14) 0.0227(11) -0.0007(11) -0.0023(10) -0.0013(11)
O11 0.0474(11) 0.090(2) 0.0261(9) -0.0321(11) -0.0020(8) -0.0011(9)
O12 0.0422(10) 0.0513(11) 0.0200(9) -0.0161(8) 0.0040(7) -0.0019(8)
N13 0.0344(13) 0.0313(14) 0.0277(12) -0.0003(11) -0.0017(11) -0.0020(12)
O14 0.055(2) 0.080(2) 0.057(2) 0.000 -0.007(2) 0.000
loop_
_atom_site_label
_atom_site_occupancy
_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_type_symbol
C1 1 .14488(7) .1020(3) -.0741(3) .0275(6) Uani d . C
C2 1 .11991(7) .2674(3) -.0355(3) .0226(5) Uani d . C
C3 1 .07362(7) .2578(4) -0.1198(3) .0297(6) Uani d . C
C4 1 .19270(7) .1048(3) -.0211(3) .0257(5) Uani d . C
O5 1 .21067(5) -.0170(2) .0576(2) .0394(5) Uani d . O
O6 1 .21305(4) .2400(2) -.0703(2) .0284(4) Uani d . O
C7 1 .12184(7) .2986(3) .1689(3) .0234(5) Uani d . C
O8 1 .15726(5) .3384(2) .2441(2) .0328(4) Uani d . O
O9 1 .08760(5) .2762(2) .2519(2) .0359(5) Uani d . O
C10 1 .06964(7) .2427(3) -0.3234(3) .0281(6) Uani d . C
O11 1 .03967(6) .1620(3) -0.3981(2) .0548(6) Uani d . O
O12 1 .09878(5) .3180(2) -0.4115(2) .0378(5) Uani d . O
N13 1 .20500(8) .6007(3) .0757(4) .0313(5) Uani d . N
O14 1 0 .1405(5) .2500 .0646(8) Uani d S O
H21 1 .1342(6) .361(3) -.085(2) .009(5) Uiso d . H
H31 1 .0590(7) .163(3) -.072(3) .023(6) Uiso d . H
H11 1 .1316(7) .007(3) -.017(3) .032(6) Uiso d . H
H12 1 .1422(6) .080(3) -0.209(3) .029(6) Uiso d . H
H32 1 .0573(8) .358(3) -.095(3) .038(7) Uiso d . H
H131 1 .1901(9) .637(4) -.012(4) .046(8) Uiso d . H
H132 1 .2320(9) .575(3) .029(3) .041(7) Uiso d . H
H133 1 .1907(9) .495(4) .124(4) .069(9) Uiso d . H
H134 1 .2083(10) .670(5) .166(5) .076(11) Uiso d . H
H61 1 .2500 .2500 .0000 .078(13) Uiso d S H
H121 1 .0940(11) .300(4) -0.564(5) .095(11) Uiso d . H
H141 .33 -.0110(18) .171(8) .097(9) .022(9) Uiso d P H
H142 .33 .032(2) .201(8) .209(8) .022(9) Uiso d P H
H143 .33 .0152(18) .017(8) .192(7) .022(9) Uiso d P H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C4 C1 C2 115.8(2) yes
C3 C2 C7 113.0(2) yes
C3 C2 C1 110.5(2) yes
C7 C2 C1 109.1(2) yes
C10 C3 C2 115.4(2) yes
O5 C4 O6 123.4(2) yes
O5 C4 C1 121.3(2) yes
O6 C4 C1 115.2(2) yes
O8 C7 O9 123.9(2) yes
O8 C7 C2 117.7(2) yes
O9 C7 C2 118.4(2) yes
O11 C10 O12 122.7(2) yes
O11 C10 C3 120.3(2) yes
O12 C10 C3 117.0(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C4 1.507(3) yes
C1 C2 1.540(3) yes
C2 C3 1.528(3) yes
C2 C7 1.532(3) yes
C3 C10 1.510(3) yes
C4 O5 1.230(3) yes
C4 O6 1.292(3) yes
C7 O8 1.238(2) yes
C7 O9 1.270(3) yes
C10 O11 1.224(3) yes
C10 O12 1.288(3) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O5 C4 C1 C2 135.7(2) ?
C1 C2 C3 C10 -62.5(3) ?
C2 C3 C10 O11 147.5(2) ?
C4 C1 C2 C3 171.7(2) yes
C4 C1 C2 C7 -63.5(3) yes
C1 C2 C7 O8 69.1(3) yes
O6 C4 C1 C2 -46.7(3) yes
C1 C2 C7 O9 -108.4(2) ?
O8 C7 C2 C3 -167.5(2) yes
C7 C2 C3 C10 174.9(2) ?
O9 C7 C2 C3 15.0(3) ?
C2 C3 C10 O12 -32.6(3) yes
