#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/46/2004639.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_2004639
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          '4N1 H4 1+, C8 H6 O8 4-, H2 O1'
_chemical_formula_structural     C~4~H~6~(COO^-^)~4~.(NH~4~^+^)~4~.H~2~O
_chemical_formula_sum            'C8 H24 N4 O9'
_chemical_formula_weight         320.31
_chemical_name_systematic
;
1,2,3,4-butanetetracarboxylic acid, tetra-ammonium salt, monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                94.454(8)
_cell_angle_beta                 108.24(2)
_cell_angle_gamma                94.402(11)
_cell_formula_units_Z            2
_cell_length_a                   7.8714(7)
_cell_length_b                   8.602(2)
_cell_length_c                   12.043(2)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     767.7(2)
_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  0.048
_diffrn_reflns_av_sigmaI/netI    0.2358
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3874
_diffrn_reflns_theta_max         29.70
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.368
_refine_ls_goodness_of_fit_obs   0.350
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.369
_refine_ls_restrained_S_obs      0.350
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_obs          0.035
_refine_ls_shift/esd_max         0.32
_refine_ls_shift/esd_mean        0.042
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.1000P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.120
_refine_ls_wR_factor_obs         0.0906
_reflns_number_observed          2151
_reflns_number_total             3433
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            li1138.cif
_cod_data_source_block           bun
_cod_database_code               2004639
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_type_symbol
C1 1 .2224(2) .4371(2) -.01910(10) .0125(2) Uiso d C
C2 1 .0772(2) .46019(14) .03956(10) .0108(2) Uani d C
C3 1 .3824(2) .3654(2) .05933(11) .0136(3) Uani d C
C4 1 .0030(2) .30217(15) .06636(10) .0110(2) Uani d C
C5 1 -0.2234(2) .0470(2) .52916(11) .0144(3) Uani d C
C6 1 -.0544(2) .07116(15) .49100(10) .0129(3) Uani d C
C7 1 -0.3268(2) .1912(2) .51596(11) .0144(3) Uani d C
C8 1 .0647(2) .21956(15) .55963(11) .0138(3) Uani d C
O31 1 .41649(14) .23364(12) .02528(8) .0222(2) Uani d O
O32 1 .47097(14) .44581(12) .15509(8) .0205(2) Uani d O
O41 1 -.08862(13) .20461(11) -.01844(8) .0156(2) Uani d O
O42 1 .03655(13) .27840(11) .17272(7) .0154(2) Uani d O
O71 1 -0.37394(14) .24115(13) .41655(8) .0225(2) Uani d O
O72 1 -0.3593(2) .25521(13) .60307(8) .0244(3) Uani d O
O81 1 .09836(15) .32618(12) .50189(8) .0218(2) Uani d O
O82 1 .1191(2) .22860(12) .66982(8) .0236(3) Uani d O
N9 1 .1029(2) .05137(15) -0.14732(10) .0172(2) Uani d N
N10 1 .3258(2) .4097(2) .37652(10) .0168(2) Uani d N
N11 1 .1789(2) .5673(2) .70502(10) .0173(3) Uani d N
N12 1 .4278(2) .7782(2) .18792(11) .0189(3) Uani d N
O13 1 .39221(15) .92308(13) .79544(9) .0212(2) Uani d O
H11 1 .172(2) .375(2) -.0938(14) .015(4) Uiso d H
H12 1 .264(2) .538(2) -.0333(14) .020(4) Uiso d H
H21 1 .134(2) .5327(18) .1155(12) .004(3) Uiso d H
H51 1 -0.192(3) .024(2) .6119(16) .025(5) Uiso d H
H52 1 -0.304(3) -.044(2) .4821(15) .022(4) Uiso d H
H61 1 -.090(2) .0927(18) .4101(13) .009(4) Uiso d H
H91 1 .096(2) .091(2) -0.2164(15) .019(4) Uiso d H
H92 1 .023(3) .094(3) -0.1120(17) .035(5) Uiso d H
H93 1 .081(3) -.060(3) -0.1568(16) .030(5) Uiso d H
H94 1 .211(3) .080(3) -.0957(19) .037(6) Uiso d H
H101 1 .351(3) .516(3) .3842(16) .029(5) Uiso d H
H102 1 .258(3) .379(2) .3029(16) .021(4) Uiso d H
H103 1 .267(3) .382(3) .4259(17) .030(5) Uiso d H
H104 1 .423(3) .361(3) .3899(17) .030(5) Uiso d H
H111 1 .144(3) .459(3) .687(2) .050(7) Uiso d H
H112 1 .295(4) .584(3) .748(2) .046(6) Uiso d H
H113 1 .165(3) .601(3) .6414(19) .035(5) Uiso d H
H114 1 .105(3) .610(3) .7404(18) .038(6) Uiso d H
H121 1 .499(3) .862(3) .1915(17) .034(5) Uiso d H
H122 1 .323(3) .779(3) .1261(18) .034(5) Uiso d H
H123 1 .403(3) .780(3) .2564(18) .032(5) Uiso d H
H124 1 .465(3) .685(3) .1741(19) .041(6) Uiso d H
H131 1 .446(4) .865(3) .849(2) .054(7) Uiso d H
H132 1 .396(3) .875(3) .7305(19) .036(6) Uiso d 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C1 C2 . . 112.30(9) yes
C1 C2 C4 . . 110.57(10) yes
C1 C2 C2 . 2_565 110.72(12) yes
C4 C2 C2 . 2_565 109.69(13) yes
O31 C3 O32 . . 125.04(12) yes
O31 C3 C1 . . 118.74(11) yes
O32 C3 C1 . . 116.22(12) yes
O41 C4 O42 . . 123.76(12) yes
O41 C4 C2 . . 118.42(10) yes
O42 C4 C2 . . 117.81(11) yes
C7 C5 C6 . . 111.67(11) yes
C8 C6 C6 . 2_556 109.92(13) yes
C8 C6 C5 . . 110.01(10) yes
C6 C6 C5 2_556 . 111.83(13) yes
O72 C7 O71 . . 122.99(13) yes
O72 C7 C5 . . 119.58(12) yes
O71 C7 C5 . . 117.43(11) yes
O81 C8 O82 . . 123.89(13) yes
O81 C8 C6 . . 117.80(11) yes
O82 C8 C6 . . 118.29(11) yes
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 C3 . 1.524(2) yes
C1 C2 . 1.537(2) yes
C2 C4 . 1.535(2) yes
C2 C2 2_565 1.535(2) yes
C3 O31 . 1.252(2) yes
C3 O32 . 1.262(2) yes
C4 O41 . 1.257(2) yes
C4 O42 . 1.2607(14) yes
C5 C7 . 1.527(2) yes
C5 C6 . 1.542(2) yes
C6 C8 . 1.536(2) yes
C6 C6 2_556 1.538(3) yes
C7 O72 . 1.253(2) yes
C7 O71 . 1.258(2) yes
C8 O81 . 1.254(2) yes
C8 O82 . 1.254(2) 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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O31 C3 C1 C2 . 117.12(13) yes
O32 C3 C1 C2 . -62.92(15) ?
C3 C1 C2 C2 2_565 177.27(12) yes
C3 C1 C2 C4 . -60.95(13) yes
C1 C2 C4 O41 . -68.07(14) yes
C1 C2 C4 O42 . 112.48(12) ?
O71 C7 C5 C6 . 55.0(2) yes
O72 C7 C5 C6 . -124.24(13) ?
C7 C5 C6 C6 2_556 177.63(12) yes
C7 C5 C6 C8 . 55.19(14) yes
C5 C6 C8 O81 . -121.02(13) yes
C5 C6 C8 O82 . 57.4(2) ?
