#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/78/2227832.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_2227832
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 Bis(imidazolium) galactarate dihydrate
;
_journal_coeditor_code           NG5021
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2399
_journal_paper_doi               10.1107/S1600536810033532
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C3 H5 N2 +, C6 H8 O8 2-, 2H2 O'
_chemical_formula_moiety         '2(C3 H5 N2 +), C6 H8 O8 2-, 2(H2 O)'
_chemical_formula_sum            'C12 H22 N4 O10'
_chemical_formula_weight         382.34
_chemical_melting_point          435
_chemical_name_common            'imidazolium mucate dihydrate'
_chemical_name_systematic
;
Bis(imidazolium) galactarate dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                92.000(5)
_cell_angle_beta                 100.559(5)
_cell_angle_gamma                109.835(6)
_cell_formula_units_Z            1
_cell_length_a                   6.9184(4)
_cell_length_b                   7.1336(4)
_cell_length_c                   9.3652(5)
_cell_measurement_reflns_used    3387
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      3.49
_cell_volume                     425.06(5)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S CCD-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4949
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         3.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             202
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0444P)²+0.0516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                1431
_reflns_number_total             1657
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5021.cif
_cod_data_source_block           I
_cod_database_code               2227832
_cod_database_fobs_code          2227832
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_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_occupancy
O O11 0.18384(15) -0.07229(13) 0.80626(9) 0.0234(3) Uani . . 1.000
O O12 0.26773(14) -0.02982(13) 1.04961(9) 0.0207(3) Uani . . 1.000
O O21 0.19607(14) 0.29951(14) 0.78260(9) 0.0203(3) Uani . . 1.000
O O31 0.62559(14) 0.35914(13) 0.90945(10) 0.0197(3) Uani . . 1.000
C C1 0.23436(18) 0.03283(17) 0.92558(13) 0.0154(3) Uani . . 1.000
C C2 0.25848(18) 0.25478(17) 0.92684(12) 0.0151(3) Uani . . 1.000
C C3 0.48566(18) 0.38863(17) 0.99549(13) 0.0153(3) Uani . . 1.000
N N11 0.34766(19) 0.22454(18) 0.54570(12) 0.0261(4) Uani . . 1.000
N N31 0.35478(19) 0.13600(18) 0.32587(12) 0.0265(4) Uani . . 1.000
C C21 0.2302(2) 0.1404(2) 0.41585(14) 0.0269(4) Uani . . 1.000
C C41 0.5588(2) 0.2202(2) 0.40018(15) 0.0302(5) Uani . . 1.000
C C51 0.5544(2) 0.2764(2) 0.53780(15) 0.0285(4) Uani . . 1.000
O O1W -0.02769(16) 0.53271(15) 0.78655(11) 0.0244(3) Uani . . 1.000
H H22 0.118(3) 0.373(3) 0.7852(19) 0.046(5) Uiso . . 1.000
H H2 0.16380 0.28050 0.98780 0.0180 Uiso calc R 1.000
H H3 0.52450 0.35200 1.09610 0.0180 Uiso calc R 1.000
H H32 0.657(3) 0.260(3) 0.9315(18) 0.040(5) Uiso . . 1.000
H H11 0.301(3) 0.245(3) 0.625(2) 0.048(5) Uiso . . 1.000
H H21 0.08100 0.09150 0.39160 0.0320 Uiso . . 1.000
H H31 0.318(3) 0.084(3) 0.233(2) 0.044(5) Uiso . . 1.000
H H41 0.68070 0.23610 0.36180 0.0360 Uiso calc R 1.000
H H51 0.67240 0.34010 0.61480 0.0340 Uiso calc R 1.000
H H11W 0.043(3) 0.660(4) 0.803(2) 0.057(6) Uiso . . 1.000
H H12W -0.127(4) 0.500(3) 0.835(2) 0.059(6) Uiso . . 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O21 H22 . . . 108.6(11) no
C3 O31 H32 . . . 110.6(13) no
H11W O1W H12W . . . 111(2) no
C21 N11 C51 . . . 108.65(12) no
C21 N31 C41 . . . 108.66(11) no
C51 N11 H11 . . . 125.3(14) no
C21 N11 H11 . . . 126.1(14) no
C41 N31 H31 . . . 123.6(14) no
C21 N31 H31 . . . 127.7(14) no
O12 C1 C2 . . . 116.02(10) no
O11 C1 O12 . . . 124.82(11) no
O11 C1 C2 . . . 119.16(10) no
O21 C2 C3 . . . 111.32(10) no
O21 C2 C1 . . . 110.05(9) no
C1 C2 C3 . . . 110.45(10) no
O31 C3 C2 . . . 109.98(9) no
C2 C3 C3 . . 2_667 112.11(10) no
O31 C3 C3 . . 2_667 107.52(10) no
O21 C2 H2 . . . 108.00 no
C3 C2 H2 . . . 108.00 no
C1 C2 H2 . . . 108.00 no
O31 C3 H3 . . . 109.00 no
C2 C3 H3 . . . 109.00 no
C3 C3 H3 2_667 . . 109.00 no
N11 C21 N31 . . . 108.63(13) no
N31 C41 C51 . . . 107.15(13) no
N11 C51 C41 . . . 106.92(12) no
N31 C21 H21 . . . 126.00 no
N11 C21 H21 . . . 126.00 no
N31 C41 H41 . . . 126.00 no
C51 C41 H41 . . . 126.00 no
N11 C51 H51 . . . 127.00 no
C41 C51 H51 . . . 127.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C1 . . 1.2465(15) no
O12 C1 . . 1.2690(15) no
O21 C2 . . 1.4223(14) no
O31 C3 . . 1.4293(16) no
O21 H22 . . 0.87(2) no
O31 H32 . . 0.83(2) no
O1W H11W . . 0.87(3) no
O1W H12W . . 0.86(3) no
N11 C21 . . 1.3249(17) no
N11 C51 . . 1.367(2) no
N31 C21 . . 1.3178(19) no
N31 C41 . . 1.369(2) no
N11 H11 . . 0.89(2) no
N31 H31 . . 0.890(18) no
C1 C2 . . 1.5341(16) no
C2 C3 . . 1.5375(18) no
C3 C3 . 2_667 1.5303(16) no
C2 H2 . . 1.0000 no
C3 H3 . . 1.0000 no
C41 C51 . . 1.345(2) no
C21 H21 . . 0.9500 no
C41 H41 . . 0.9500 no
C51 H51 . . 0.9500 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N11 H11 O21 . 0.89(2) 1.84(2) 2.7311(15) 175.9(19) yes
N31 H31 O12 1_554 0.890(18) 1.795(19) 2.6810(14) 174(2) yes
O21 H22 O1W . 0.87(2) 1.76(2) 2.6324(15) 177(2) yes
O31 H32 O12 2_657 0.83(2) 1.89(2) 2.7104(13) 170.9(16) yes
O1W H11W O11 1_565 0.87(3) 1.82(3) 2.6799(14) 170.9(18) yes
O1W H12W O31 1_455 0.86(3) 1.94(3) 2.7763(15) 164.4(19) yes
C21 H21 O11 2_556 0.95 2.32 3.0935(17) 138 no
C41 H41 O11 2_656 0.95 2.42 3.2273(18) 142 no
C51 H51 O1W 1_655 0.95 2.34 3.2827(18) 173 no
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 N11 C51 C41 . . . . -0.42(16) no
C51 N11 C21 N31 . . . . 0.31(16) no
C21 N31 C41 C51 . . . . -0.19(16) no
C41 N31 C21 N11 . . . . -0.08(16) no
O11 C1 C2 O21 . . . . 5.67(17) no
O12 C1 C2 O21 . . . . -174.06(11) no
O12 C1 C2 C3 . . . . 62.63(14) no
O11 C1 C2 C3 . . . . -117.63(13) no
O21 C2 C3 O31 . . . . -59.81(13) no
C1 C2 C3 C3 . . . 2_667 -177.68(10) no
C1 C2 C3 O31 . . . . 62.76(12) no
O21 C2 C3 C3 . . . 2_667 59.76(13) no
O31 C3 C3 O31 . . 2_667 2_667 179.98(12) no
C2 C3 C3 O31 . . 2_667 2_667 59.01(12) no
C2 C3 C3 C2 . . 2_667 2_667 -179.98(12) no
O31 C3 C3 C2 . . 2_667 2_667 -59.01(12) no
N31 C41 C51 N11 . . . . 0.36(16) no
