#------------------------------------------------------------------------------
#$Date: 2021-02-05 16:52:16 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/87/2108743.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_2108743
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_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                116.22(3)
_cell_angle_beta                 101.88(3)
_cell_angle_gamma                91.18(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9990(10)
_cell_length_b                   8.378(2)
_cell_length_c                   9.249(2)
_cell_measurement_reflns_used    4533
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      56.07
_cell_measurement_theta_min      4
_cell_volume                     472.3(2)
_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      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.920
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4533
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.034
_diffrn_reflns_theta_min         2.749
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.1201
_exptl_absorpt_correction_T_min  0.9552
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrysAlis v171.33.42'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.450
_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         0.280
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.269
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.069
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0322P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0752
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1657
_reflns_number_total             2104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lo5078sup1.cif
_cod_data_source_block           m120
_cod_depositor_comments
'Adding full bibliography for 2108742--2108745.cif.'
_cod_original_formula_sum        'C7.50 H10 N3 O4'
_cod_database_code               2108743
_cod_database_fobs_code          2108743
_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 0.22235(6) 0.42389(4) 0.38854(4) 0.02189(11) Uani 1 1 d . . . . .
O2 O 0.21580(6) 0.17148(5) 0.16269(4) 0.02253(11) Uani 1 1 d . . . . .
O3 O 0.33428(6) 0.14745(5) 0.65179(4) 0.02743(11) Uani 1 1 d . . . . .
O4 O 0.08703(6) 0.05841(5) 0.42726(4) 0.02960(11) Uani 1 1 d . . . . .
C1 C 0.26718(8) 0.26692(6) 0.31731(6) 0.01624(13) Uani 1 1 d . . . . .
C2 C 0.38750(8) 0.19316(7) 0.42511(6) 0.02025(14) Uani 1 1 d . . . . .
C3 C 0.26421(8) 0.13092(6) 0.51255(6) 0.01868(14) Uani 1 1 d . . . . .
N1A1 N 0.29114(7) 0.62721(5) 0.71723(5) 0.01849(12) Uani 1 1 d . . . . .
C1A C 0.23165(8) 0.78764(6) 0.78811(6) 0.01830(14) Uani 1 1 d . . . . .
N1A2 N 0.29938(7) 0.85690(5) 0.95114(5) 0.01834(12) Uani 1 1 d . . . . .
C2A C 0.40577(8) 0.73638(7) 0.98651(6) 0.02086(14) Uani 1 1 d . . . . .
C3A C 0.40032(8) 0.59334(7) 0.84027(6) 0.02058(15) Uani 1 1 d . . . . .
N1B1 N 0.07094(13) 0.40792(10) 1.04915(10) 0.0197(2) Uani 0.5 1 d D . P A 1
C1B C 0.00446(17) 0.37792(12) 0.89213(12) 0.0192(3) Uani 0.5 1 d . . P A 1
N1B2 N -0.06134(13) 0.52466(10) 0.89293(10) 0.0173(2) Uani 0.5 1 d D . P A 1
C2B C -0.03820(17) 0.65449(13) 1.05496(12) 0.0197(3) Uani 0.5 1 d . . P A 1
C3B C 0.04367(17) 0.58037(12) 1.15121(12) 0.0191(3) Uani 0.5 1 d . . P A 1
H3B H 0.0755(17) 0.6307(13) 1.2713(12) 0.018(3) Uiso 0.5 1 d . . P B 1
H2B H -0.0765(16) 0.7624(13) 1.0744(12) 0.017(3) Uiso 0.5 1 d . . P C 1
H1B2 H -0.1209(19) 0.5277(16) 0.7917(14) 0.041(4) Uiso 0.5 1 d D . P D 1
H1B1 H 0.123(2) 0.3221(15) 1.0825(15) 0.046(4) Uiso 0.5 1 d D . P E 1
H1B H 0.0135(17) 0.2716(15) 0.7990(14) 0.032(4) Uiso 0.5 1 d . . P F 1
H1A1 H 0.2665(9) 0.5508(8) 0.6007(7) 0.0385(19) Uiso 1 1 d . . . . .
H1A H 0.1513(9) 0.8425(7) 0.7304(7) 0.0280(17) Uiso 1 1 d . . . . .
H1A2 H 0.2749(9) 0.9647(8) 1.0304(7) 0.0360(18) Uiso 1 1 d . . . . .
H2A H 0.4663(9) 0.7641(7) 1.0975(7) 0.0267(16) Uiso 1 1 d . . . . .
H3A H 0.4520(9) 0.4852(7) 0.8159(7) 0.0297(17) Uiso 1 1 d . . . . .
H4 H 0.0000 0.0000 0.5000 0.101(5) Uiso 1 2 d S . P . .
H21 H 0.4932(8) 0.2817(7) 0.5054(7) 0.0248(16) Uiso 1 1 d . . . . .
H22 H 0.4435(8) 0.0882(7) 0.3563(6) 0.0248(16) 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 111.59(4) . . ?
O2 C1 O1 122.60(6) . . ?
O2 C1 C2 119.57(5) . . ?
O1 C1 C2 117.83(5) . . ?
C1 C2 C3 112.60(5) . . ?
C1 C2 H21 110.0(4) . . ?
C3 C2 H21 109.6(4) . . ?
C1 C2 H22 109.8(4) . . ?
C3 C2 H22 106.3(4) . . ?
H21 C2 H22 108.3(5) . . ?
O3 C3 O4 124.49(6) . . ?
O3 C3 C2 120.63(5) . . ?
O4 C3 C2 114.86(5) . . ?
C1A N1A1 C3A 108.36(5) . . ?
C1A N1A1 H1A1 125.7(4) . . ?
C3A N1A1 H1A1 125.9(4) . . ?
N1A2 C1A N1A1 108.70(6) . . ?
N1A2 C1A H1A 126.0(3) . . ?
N1A1 C1A H1A 125.3(3) . . ?
C1A N1A2 C2A 108.73(5) . . ?
C1A N1A2 H1A2 126.7(4) . . ?
C2A N1A2 H1A2 124.4(4) . . ?
C3A C2A N1A2 106.79(6) . . ?
C3A C2A H2A 132.8(4) . . ?
N1A2 C2A H2A 120.4(4) . . ?
C2A C3A N1A1 107.43(6) . . ?
C2A C3A H3A 131.0(4) . . ?
N1A1 C3A H3A 121.5(4) . . ?
N1B2 N1B1 C2B 145.6(2) 2_567 2_567 ?
N1B2 N1B1 C1B 122.52(17) 2_567 . ?
C2B N1B1 C1B 24.32(9) 2_567 . ?
N1B2 N1B1 C3B 15.52(13) 2_567 . ?
C2B N1B1 C3B 131.92(14) 2_567 . ?
C1B N1B1 C3B 107.97(9) . . ?
N1B2 N1B1 C1B 35.86(13) 2_567 2_567 ?
C2B N1B1 C1B 110.83(12) 2_567 2_567 ?
C1B N1B1 C1B 86.92(8) . 2_567 ?
C3B N1B1 C1B 21.09(6) . 2_567 ?
N1B2 N1B1 C3B 108.97(15) 2_567 2_567 ?
C2B N1B1 C3B 37.58(10) 2_567 2_567 ?
C1B N1B1 C3B 13.55(5) . 2_567 ?
C3B N1B1 C3B 94.48(8) . 2_567 ?
C1B N1B1 C3B 73.41(6) 2_567 2_567 ?
N1B2 N1B1 H1B1 112.0(7) 2_567 . ?
C2B N1B1 H1B1 100.9(7) 2_567 . ?
C1B N1B1 H1B1 125.1(7) . . ?
C3B N1B1 H1B1 126.9(7) . . ?
C1B N1B1 H1B1 147.8(7) 2_567 . ?
C3B N1B1 H1B1 138.5(7) 2_567 . ?
C2B C1B C3B 167.5(2) 2_567 2_567 ?
C2B C1B N1B2 139.49(15) 2_567 . ?
C3B C1B N1B2 31.24(9) 2_567 . ?
C2B C1B N1B1 31.55(10) 2_567 . ?
C3B C1B N1B1 139.28(14) 2_567 . ?
N1B2 C1B N1B1 108.42(8) . . ?
C2B C1B N1B2 48.12(11) 2_567 2_567 ?
C3B C1B N1B2 122.32(13) 2_567 2_567 ?
N1B2 C1B N1B2 91.56(8) . 2_567 ?
N1B1 C1B N1B2 16.96(5) . 2_567 ?
C2B C1B N1B1 124.05(13) 2_567 2_567 ?
C3B C1B N1B1 46.34(10) 2_567 2_567 ?
N1B2 C1B N1B1 15.44(5) . 2_567 ?
N1B1 C1B N1B1 93.08(8) . 2_567 ?
N1B2 C1B N1B1 76.17(6) 2_567 2_567 ?
C2B C1B H1B 93.2(9) 2_567 . ?
C3B C1B H1B 96.5(8) 2_567 . ?
N1B2 C1B H1B 127.2(8) . . ?
N1B1 C1B H1B 124.2(8) . . ?
N1B2 C1B H1B 141.1(8) 2_567 . ?
N1B1 C1B H1B 142.7(8) 2_567 . ?
N1B1 N1B2 C3B 153.1(2) 2_567 2_567 ?
N1B1 N1B2 C1B 128.69(17) 2_567 . ?
C3B N1B2 C1B 25.84(9) 2_567 . ?
N1B1 N1B2 C2B 20.17(12) 2_567 . ?
C3B N1B2 C2B 134.90(13) 2_567 . ?
C1B N1B2 C2B 109.37(9) . . ?
N1B1 N1B2 C1B 40.52(13) 2_567 2_567 ?
C3B N1B2 C1B 113.91(12) 2_567 2_567 ?
C1B N1B2 C1B 88.44(8) . 2_567 ?
C2B N1B2 C1B 20.99(6) . 2_567 ?
N1B1 N1B2 C2B 115.38(15) 2_567 2_567 ?
C3B N1B2 C2B 38.87(9) 2_567 2_567 ?
C1B N1B2 C2B 13.31(5) . 2_567 ?
C2B N1B2 C2B 96.14(8) . 2_567 ?
C1B N1B2 C2B 75.18(6) 2_567 2_567 ?
N1B1 N1B2 H1B2 109.8(7) 2_567 . ?
C3B N1B2 H1B2 95.2(7) 2_567 . ?
C1B N1B2 H1B2 120.9(7) . . ?
C2B N1B2 H1B2 129.6(7) . . ?
C1B N1B2 H1B2 150.3(7) 2_567 . ?
C2B N1B2 H1B2 134.0(7) 2_567 . ?
C1B C2B N1B1 124.13(17) 2_567 2_567 ?
C1B C2B C3B 6.34(13) 2_567 . ?
N1B1 C2B C3B 119.85(13) 2_567 . ?
C1B C2B N1B2 110.90(14) 2_567 . ?
N1B1 C2B N1B2 14.18(8) 2_567 . ?
C3B C2B N1B2 106.22(9) . . ?
C1B C2B N1B2 27.20(10) 2_567 2_567 ?
N1B1 C2B N1B2 97.44(11) 2_567 2_567 ?
C3B C2B N1B2 22.41(5) . 2_567 ?
N1B2 C2B N1B2 83.86(8) . 2_567 ?
C1B C2B H2B 129.8(7) 2_567 . ?
N1B1 C2B H2B 105.4(7) 2_567 . ?
C3B C2B H2B 134.7(7) . . ?
N1B2 C2B H2B 119.1(7) . . ?
N1B2 C2B H2B 157.0(7) 2_567 . ?
C1B C3B N1B2 122.92(16) 2_567 2_567 ?
C1B C3B C2B 6.14(12) 2_567 . ?
N1B2 C3B C2B 118.72(12) 2_567 . ?
C1B C3B N1B1 112.57(13) 2_567 . ?
N1B2 C3B N1B1 11.36(9) 2_567 . ?
C2B C3B N1B1 108.02(9) . . ?
C1B C3B N1B1 27.17(10) 2_567 2_567 ?
N1B2 C3B N1B1 96.16(11) 2_567 2_567 ?
C2B C3B N1B1 22.57(5) . 2_567 ?
N1B1 C3B N1B1 85.52(8) . 2_567 ?
C1B C3B H3B 124.2(7) 2_567 . ?
N1B2 C3B H3B 111.9(7) 2_567 . ?
C2B C3B H3B 129.0(7) . . ?
N1B1 C3B H3B 122.9(7) . . ?
N1B1 C3B H3B 151.3(7) 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 1.2643(7) . ?
O2 C1 1.2569(8) . ?
O3 C3 1.2239(8) . ?
O4 C3 1.2930(8) . ?
O4 H4 1.2290(5) . ?
C1 C2 1.5184(9) . ?
C2 C3 1.5205(10) . ?
C2 H21 0.956(5) . ?
C2 H22 0.977(5) . ?
N1A1 C1A 1.3291(8) . ?
N1A1 C3A 1.3768(9) . ?
N1A1 H1A1 0.954(6) . ?
C1A N1A2 1.3252(8) . ?
C1A H1A 0.957(7) . ?
N1A2 C2A 1.3797(8) . ?
N1A2 H1A2 0.925(6) . ?
C2A C3A 1.3460(9) . ?
C2A H2A 0.945(6) . ?
C3A H3A 0.932(6) . ?
N1B1 N1B2 0.5996(11) 2_567 ?
N1B1 C2B 0.8441(13) 2_567 ?
N1B1 C1B 1.3354(14) . ?
N1B1 C3B 1.3767(13) . ?
N1B1 C1B 1.7574(14) 2_567 ?
N1B1 C3B 1.9076(16) 2_567 ?
N1B1 H1B1 0.952(14) . ?
C1B C2B 0.6644(15) 2_567 ?
C1B C3B 0.6850(15) 2_567 ?
C1B N1B2 1.3192(14) . ?
C1B N1B2 1.7331(14) 2_567 ?
C1B N1B1 1.7574(14) 2_567 ?
C1B H1B 0.941(10) . ?
N1B2 N1B1 0.5996(11) 2_567 ?
N1B2 C3B 0.8150(12) 2_567 ?
N1B2 C2B 1.3812(13) . ?
N1B2 C1B 1.7331(14) 2_567 ?
N1B2 C2B 1.8747(16) 2_567 ?
N1B2 H1B2 0.955(13) . ?
C2B C1B 0.6645(15) 2_567 ?
C2B N1B1 0.8440(13) 2_567 ?
C2B C3B 1.3414(17) . ?
C2B N1B2 1.8747(16) 2_567 ?
C2B H2B 0.899(11) . ?
C3B C1B 0.6850(15) 2_567 ?
C3B N1B2 0.8150(12) 2_567 ?
C3B N1B1 1.9076(16) 2_567 ?
C3B H3B 0.970(10) . ?
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 1.2290(5) 2.4427(11) 3.1611(12) 114.77(3) 2_556
O4 H4 O4 1.2290(5) 1.2290(5) 2.4580(11) 180.0 2_556
C2 H21 O1 0.956(5) 2.805(6) 3.6791(18) 152.5(5) 2_666
C2 H22 O3 0.977(5) 2.523(6) 3.3833(13) 146.8(5) 2_656
N1A1 H1A1 O1 0.954(6) 1.723(6) 2.6764(12) 176.7(7) .
C1A H1A O4 0.957(7) 2.393(7) 3.3416(12) 171.3(5) 2_566
N1A2 H1A2 O2 0.925(6) 1.742(6) 2.6637(12) 174.1(6) 1_566
C2A H2A O3 0.945(6) 2.232(6) 3.1611(14) 167.5(6) 2_667
C3A H3A O3 0.932(6) 2.566(5) 3.3242(14) 138.8(4) .
C3B H3B O1 0.970(10) 2.551(12) 3.0954(15) 115.5(8) 1_556
C2B H2B O2 0.899(11) 2.506(12) 3.0596(15) 120.3(7) 2_566
C2B H2B O4 0.899(11) 3.050(9) 3.524(2) 114.8(8) 1_566
N1B2 H1B2 O1 0.955(13) 1.889(13) 2.8349(13) 170.2(10) 2_566
N1B2 H1B2 O2 0.955(13) 2.493(13) 2.9925(13) 112.6(8) 2_566
N1B1 H1B1 O1 0.952(14) 2.501(13) 3.0410(13) 116.0(8) 1_556
N1B1 H1B1 O2 0.952(14) 1.796(14) 2.7453(13) 174.8(12) 1_556
C1B H1B O3 0.941(10) 2.842(12) 3.5358(17) 131.4(9) .
C1B H1B O4 0.941(10) 2.592(10) 3.4760(19) 156.5(11) 2_556
