#------------------------------------------------------------------------------
#$Date: 2021-02-05 16:52:16 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/87/2108742.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_2108742
loop_
_publ_author_name
'Ławniczak, Paweł'
'Pogorzelec-Glaser, Katarzyna'
'Pietraszko, Adam'
'Hilczer, Bożena'
_publ_section_title
;
 Effect of disordered imidazole substructure on proton dynamics in
 imidazolium malonic acid salt
;
_journal_coeditor_code           LO5078
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              31
_journal_page_last               40
_journal_paper_doi               10.1107/S2052520620014365
_journal_volume                  77
_journal_year                    2021
_chemical_formula_moiety         'C6 H5 O8, 3(C3 H5 N2)'
_chemical_formula_sum            'C7.5 H10 N3 O4'
_chemical_formula_weight         206.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                117.560(12)
_cell_angle_beta                 102.07(2)
_cell_angle_gamma                89.390(15)
_cell_formula_units_Z            2
_cell_length_a                   6.9050(13)
_cell_length_b                   8.3940(13)
_cell_length_c                   9.3390(6)
_cell_measurement_reflns_used    3204
_cell_measurement_temperature    14(2)
_cell_measurement_theta_max      56.0
_cell_measurement_theta_min      4
_cell_volume                     466.94(14)
_computing_cell_refinement       'CrysAlis v171.33.42'
_computing_data_collection       'CrysAlis v171.33.42'
_computing_data_reduction        'CrysAlis v171.33.42'
_computing_molecular_graphics    'Diamond 3.2'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      14(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.770
_diffrn_measurement_device_type  'Xcalibur Oxford Diffraction'
_diffrn_measurement_method       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.770
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3204
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.770
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.777
_diffrn_reflns_theta_min         3.032
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.231
_exptl_absorpt_correction_T_min  0.9210
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrysAlis v171.33.42'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unshaped
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.041(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0300P)²+0.6000P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1826
_reflns_number_total             2245
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lo5078sup1.cif
_cod_data_source_block           im14
_cod_depositor_comments
'Adding full bibliography for 2108742--2108745.cif.'
_cod_original_cell_volume        466.94(13)
_cod_original_formula_sum        'C7.50 H10 N3 O4'
_cod_database_code               2108742
_cod_database_fobs_code          2108742
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22167(9) 0.42469(8) 0.38829(8) 0.01345(16) Uani 1 1 d . . . . .
O2 O 0.21679(9) 0.17206(8) 0.16231(8) 0.01342(16) Uani 1 1 d . . . . .
O3 O 0.33589(10) 0.14902(9) 0.65169(8) 0.01567(17) Uani 1 1 d . . . . .
O4 O 0.08665(9) 0.05863(9) 0.42671(8) 0.01508(17) Uani 1 1 d . . . . .
C1 C 0.26845(12) 0.26749(11) 0.31685(10) 0.0103(2) Uani 1 1 d . . . . .
C2 C 0.39089(12) 0.19424(11) 0.42499(11) 0.0127(2) Uani 1 1 d . . . . .
C3 C 0.26537(12) 0.13193(11) 0.51236(11) 0.0118(2) Uani 1 1 d . . . . .
N1A1 N 0.29122(11) 0.62517(10) 0.71700(9) 0.01177(19) Uani 1 1 d . . . . .
C1A C 0.23234(12) 0.78718(11) 0.78878(11) 0.0110(2) Uani 1 1 d . . . . .
N1A2 N 0.30047(11) 0.85629(10) 0.95172(9) 0.01212(19) Uani 1 1 d . . . . .
C2A C 0.40725(13) 0.73442(11) 0.98654(11) 0.0126(2) Uani 1 1 d . . . . .
C3A C 0.40091(13) 0.58992(11) 0.83894(11) 0.0137(2) Uani 1 1 d . . . . .
N1B1 N 0.0699(2) 0.40913(19) 1.05004(18) 0.0106(4) Uani 0.5 1 d . . P A 1
C1B C 0.0045(3) 0.3765(2) 0.8932(2) 0.0110(4) Uani 0.5 1 d . . P A 1
N1B2 N -0.0628(2) 0.52312(19) 0.89048(18) 0.0116(4) Uani 0.5 1 d . . P A 1
C2B C -0.0399(2) 0.6533(2) 1.0542(2) 0.0110(4) Uani 0.5 1 d . . P A 1
C3B C 0.0431(2) 0.5817(2) 1.1512(2) 0.0103(4) Uani 0.5 1 d . . P A 1
H3B H 0.082(3) 0.633(3) 1.275(3) 0.013(6) Uiso 0.5 1 d . . P B 1
H2B H -0.072(3) 0.771(3) 1.067(3) 0.015(6) Uiso 0.5 1 d . . P C 1
H1B2 H -0.125(3) 0.539(3) 0.794(3) 0.008(5) Uiso 0.5 1 d . . P D 1
H1B1 H 0.126(4) 0.327(4) 1.087(4) 0.040(9) Uiso 0.5 1 d . . P E 1
H1B H 0.004(3) 0.265(3) 0.795(3) 0.015(6) Uiso 0.5 1 d . . P F 1
H4 H 0.0000 0.0000 0.5000 0.049(7) Uiso 1 2 d S . P . .
H21 H 0.4995(19) 0.2841(17) 0.5068(15) 0.025(3) Uiso 1 1 d . . . . .
H22 H 0.4530(18) 0.0887(16) 0.3585(14) 0.020(3) Uiso 1 1 d . . . . .
H1A1 H 0.2645(19) 0.5485(17) 0.5985(15) 0.024(3) Uiso 1 1 d . . . . .
H1A H 0.1537(18) 0.8421(16) 0.7318(14) 0.018(3) Uiso 1 1 d . . . . .
H1A2 H 0.280(3) 0.968(2) 1.030(2) 0.055(5) Uiso 1 1 d . . . . .
H2A H 0.4734(18) 0.7595(15) 1.0986(14) 0.016(3) Uiso 1 1 d . . . . .
H3A H 0.4537(18) 0.4759(16) 0.8074(14) 0.021(3) Uiso 1 1 d . . . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O4 H4 111.45(7) . . ?
O1 C1 O2 121.87(9) . . ?
O1 C1 C2 117.35(7) . . ?
O2 C1 C2 120.78(7) . . ?
C1 C2 C3 113.24(7) . . ?
C1 C2 H21 110.3(9) . . ?
C3 C2 H21 110.2(9) . . ?
C1 C2 H22 110.8(8) . . ?
C3 C2 H22 105.8(9) . . ?
H21 C2 H22 106.2(10) . . ?
O3 C3 O4 123.99(10) . . ?
O3 C3 C2 120.79(8) . . ?
O4 C3 C2 115.20(8) . . ?
C1A N1A1 C3A 108.30(7) . . ?
C1A N1A1 H1A1 124.3(9) . . ?
C3A N1A1 H1A1 127.3(9) . . ?
N1A1 C1A N1A2 108.33(9) . . ?
N1A1 C1A H1A 124.6(7) . . ?
N1A2 C1A H1A 127.1(7) . . ?
C1A N1A2 C2A 109.67(7) . . ?
C1A N1A2 H1A2 125.8(12) . . ?
C2A N1A2 H1A2 124.5(12) . . ?
C3A C2A N1A2 105.63(9) . . ?
C3A C2A H2A 131.3(7) . . ?
N1A2 C2A H2A 123.1(7) . . ?
C2A C3A N1A1 108.07(8) . . ?
C2A C3A H3A 132.9(8) . . ?
N1A1 C3A H3A 119.0(7) . . ?
N1B2 N1B1 C2B 148.0(3) 2_567 2_567 ?
N1B2 N1B1 C1B 125.2(3) 2_567 . ?
C2B N1B1 C1B 23.43(16) 2_567 . ?
N1B2 N1B1 C3B 17.4(2) 2_567 . ?
C2B N1B1 C3B 131.7(2) 2_567 . ?
C1B N1B1 C3B 108.41(16) . . ?
N1B2 N1B1 C1B 38.7(2) 2_567 2_567 ?
C2B N1B1 C1B 109.9(2) 2_567 2_567 ?
C1B N1B1 C1B 86.65(12) . 2_567 ?
C3B N1B1 C1B 21.79(10) . 2_567 ?
N1B2 N1B1 C3B 111.7(3) 2_567 2_567 ?
C2B N1B1 C3B 36.75(16) 2_567 2_567 ?
C1B N1B1 C3B 13.47(9) . 2_567 ?
C3B N1B1 C3B 94.98(13) . 2_567 ?
C1B N1B1 C3B 73.21(10) 2_567 2_567 ?
N1B2 N1B1 H1B1 107.7(16) 2_567 . ?
C2B N1B1 H1B1 103.6(16) 2_567 . ?
C1B N1B1 H1B1 127.0(16) . . ?
C3B N1B1 H1B1 124.6(16) . . ?
C1B N1B1 H1B1 146.4(16) 2_567 . ?
C3B N1B1 H1B1 140.4(16) 2_567 . ?
C2B C1B C3B 168.9(4) 2_567 2_567 ?
C2B C1B N1B2 140.3(2) 2_567 . ?
C3B C1B N1B2 30.46(16) 2_567 . ?
C2B C1B N1B1 30.88(17) 2_567 . ?
C3B C1B N1B1 139.8(2) 2_567 . ?
N1B2 C1B N1B1 109.62(14) . . ?
C2B C1B N1B1 124.0(2) 2_567 2_567 ?
C3B C1B N1B1 46.56(17) 2_567 2_567 ?
N1B2 C1B N1B1 16.34(9) . 2_567 ?
N1B1 C1B N1B1 93.35(12) . 2_567 ?
C2B C1B N1B2 46.84(18) 2_567 2_567 ?
C3B C1B N1B2 123.7(2) 2_567 2_567 ?
N1B2 C1B N1B2 93.54(13) . 2_567 ?
N1B1 C1B N1B2 16.15(8) . 2_567 ?
N1B1 C1B N1B2 77.23(10) 2_567 2_567 ?
C2B C1B H1B 95.9(17) 2_567 . ?
C3B C1B H1B 93.4(17) 2_567 . ?
N1B2 C1B H1B 123.7(17) . . ?
N1B1 C1B H1B 126.7(17) . . ?
N1B1 C1B H1B 139.9(16) 2_567 . ?
N1B2 C1B H1B 142.8(17) 2_567 . ?
N1B1 N1B2 C3B 149.9(4) 2_567 2_567 ?
N1B1 N1B2 C1B 125.0(3) 2_567 . ?
C3B N1B2 C1B 25.81(16) 2_567 . ?
N1B1 N1B2 C2B 18.8(2) 2_567 . ?
C3B N1B2 C2B 132.1(2) 2_567 . ?
C1B N1B2 C2B 106.58(16) . . ?
N1B1 N1B2 C1B 38.7(2) 2_567 2_567 ?
C3B N1B2 C1B 112.0(2) 2_567 2_567 ?
C1B N1B2 C1B 86.46(13) . 2_567 ?
C2B N1B2 C1B 20.14(10) . 2_567 ?
N1B1 N1B2 C2B 112.1(3) 2_567 2_567 ?
C3B N1B2 C2B 38.53(17) 2_567 2_567 ?
C1B N1B2 C2B 12.89(9) . 2_567 ?
C2B N1B2 C2B 93.72(13) . 2_567 ?
C1B N1B2 C2B 73.59(10) 2_567 2_567 ?
N1B1 N1B2 H1B2 106.2(12) 2_567 . ?
C3B N1B2 H1B2 102.7(12) 2_567 . ?
C1B N1B2 H1B2 128.5(12) . . ?
C2B N1B2 H1B2 124.9(12) . . ?
C1B N1B2 H1B2 144.9(12) 2_567 . ?
C2B N1B2 H1B2 141.2(12) 2_567 . ?
C1B C2B N1B1 125.7(3) 2_567 2_567 ?
C1B C2B C3B 5.72(19) 2_567 . ?
N1B1 C2B C3B 121.1(2) 2_567 . ?
C1B C2B N1B2 113.0(2) 2_567 . ?
N1B1 C2B N1B2 13.16(14) 2_567 . ?
C3B C2B N1B2 108.23(15) . . ?
C1B C2B N1B2 26.80(17) 2_567 2_567 ?
N1B1 C2B N1B2 99.10(18) 2_567 2_567 ?
C3B C2B N1B2 22.00(8) . 2_567 ?
N1B2 C2B N1B2 86.28(13) . 2_567 ?
C1B C2B C3B 95.8(2) 2_567 2_567 ?
N1B1 C2B C3B 30.09(15) 2_567 2_567 ?
C3B C2B C3B 91.05(12) . 2_567 ?
N1B2 C2B C3B 17.24(10) . 2_567 ?
N1B2 C2B C3B 69.07(9) 2_567 2_567 ?
C1B C2B H2B 133.3(14) 2_567 . ?
N1B1 C2B H2B 101.0(14) 2_567 . ?
C3B C2B H2B 137.7(13) . . ?
N1B2 C2B H2B 113.6(14) . . ?
N1B2 C2B H2B 159.5(13) 2_567 . ?
C3B C2B H2B 130.8(14) 2_567 . ?
C1B C3B N1B2 123.7(3) 2_567 2_567 ?
C1B C3B C2B 5.41(18) 2_567 . ?
N1B2 C3B C2B 119.5(2) 2_567 . ?
C1B C3B N1B1 111.7(2) 2_567 . ?
N1B2 C3B N1B1 12.74(16) 2_567 . ?
C2B C3B N1B1 107.15(15) . . ?
C1B C3B N1B1 26.73(16) 2_567 2_567 ?
N1B2 C3B N1B1 97.31(19) 2_567 2_567 ?
C2B C3B N1B1 22.15(8) . 2_567 ?
N1B1 C3B N1B1 85.02(13) . 2_567 ?
C1B C3B C2B 93.4(2) 2_567 2_567 ?
N1B2 C3B C2B 30.62(16) 2_567 2_567 ?
C2B C3B C2B 88.95(12) . 2_567 ?
N1B1 C3B C2B 18.22(10) . 2_567 ?
N1B1 C3B C2B 66.80(9) 2_567 2_567 ?
C1B C3B H3B 127.1(15) 2_567 . ?
N1B2 C3B H3B 108.8(15) 2_567 . ?
C2B C3B H3B 131.7(14) . . ?
N1B1 C3B H3B 121.2(14) . . ?
N1B1 C3B H3B 153.8(14) 2_567 . ?
C2B C3B H3B 139.4(14) 2_567 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2478(10) . ?
O2 C1 1.2541(10) . ?
O3 C3 1.2307(13) . ?
O4 C3 1.2997(10) . ?
O4 H4 1.2482(8) . ?
C1 C2 1.5229(14) . ?
C2 C3 1.5462(15) . ?
C2 H21 0.977(11) . ?
C2 H22 0.974(12) . ?
N1A1 C1A 1.3125(11) . ?
N1A1 C3A 1.3800(14) . ?
N1A1 H1A1 0.965(12) . ?
C1A N1A2 1.3278(12) . ?
C1A H1A 0.944(14) . ?
N1A2 C2A 1.3739(13) . ?
N1A2 H1A2 0.913(16) . ?
C2A C3A 1.3423(12) . ?
C2A H2A 0.973(12) . ?
C3A H3A 0.955(13) . ?
N1B1 N1B2 0.5940(18) 2_567 ?
N1B1 C2B 0.843(2) 2_567 ?
N1B1 C1B 1.334(3) . ?
N1B1 C3B 1.352(2) . ?
N1B1 C1B 1.730(2) 2_567 ?
N1B1 C3B 1.915(3) 2_567 ?
N1B1 H1B1 0.95(4) . ?
C1B C2B 0.653(3) 2_567 ?
C1B C3B 0.691(3) 2_567 ?
C1B N1B2 1.320(2) . ?
C1B N1B1 1.730(2) 2_567 ?
C1B N1B2 1.745(2) 2_567 ?
C1B H1B 0.96(2) . ?
N1B2 N1B1 0.5940(18) 2_567 ?
N1B2 C3B 0.805(2) 2_567 ?
N1B2 C2B 1.383(2) . ?
N1B2 C1B 1.745(2) 2_567 ?
N1B2 C2B 1.870(3) 2_567 ?
N1B2 H1B2 0.98(2) . ?
C2B C1B 0.653(3) 2_567 ?
C2B N1B1 0.843(2) 2_567 ?
C2B C3B 1.338(3) . ?
C2B N1B2 1.870(3) 2_567 ?
C2B C3B 2.013(2) 2_567 ?
C2B H2B 0.97(3) . ?
C3B C1B 0.691(3) 2_567 ?
C3B N1B2 0.805(2) 2_567 ?
C3B N1B1 1.915(3) 2_567 ?
C3B C2B 2.013(2) 2_567 ?
C3B H3B 1.00(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O3 1.2482(8) 2.4492(9) 3.1813(12) 114.79(4) 2_556
C2 H21 O1 0.977(11) 2.782(13) 3.6741(14) 152.2(12) 2_666
C2 H22 O3 0.974(12) 2.437(13) 3.3036(13) 148.1(11) 2_656
N1A1 H1A1 O1 0.965(12) 1.702(12) 2.6658(11) 176.4(14) .
C1A H1A O4 0.944(14) 2.393(14) 3.3275(14) 170.6(10) 2_566
N1A2 H1A2 O2 0.913(16) 1.707(16) 2.6165(10) 173.7(16) 1_566
C2A H2A O3 0.973(12) 2.201(11) 3.1606(14) 168.9(11) 2_667
C3A H3A O3 0.955(13) 2.483(12) 3.2672(12) 139.3(9) .
C3B H3B O1 1.00(2) 2.52(3) 3.112(2) 117.1(16) 1_556
C2B H2B O2 0.97(3) 2.42(3) 3.066(2) 123.7(15) 2_566
C2B H2B O4 0.97(3) 3.052(19) 3.5045(17) 110.0(16) 1_566
N1B2 H1B2 O1 0.98(2) 1.85(2) 2.833(2) 175(2) 2_566
N1B2 H1B2 O2 0.98(2) 2.37(2) 2.9682(19) 118.8(14) 2_566
N1B1 H1B1 O1 0.95(4) 2.48(3) 3.0546(19) 119(2) 1_556
N1B1 H1B1 O2 0.95(4) 1.80(4) 2.744(2) 176(3) 1_556
C1B H1B O3 0.96(2) 2.83(2) 3.471(2) 124.9(17) .
C1B H1B O4 0.96(2) 2.52(2) 3.4392(17) 160(2) 2_556
