#------------------------------------------------------------------------------
#$Date: 2021-02-05 16:52:16 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/87/2108744.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_2108744
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                116.40(3)
_cell_angle_beta                 101.57(3)
_cell_angle_gamma                91.09(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9800(10)
_cell_length_b                   8.400(2)
_cell_length_c                   9.230(2)
_cell_measurement_reflns_used    3296
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      56.1
_cell_measurement_theta_min      4
_cell_volume                     471.3(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      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.866
_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  0.0243
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3296
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.516
_diffrn_reflns_theta_min         3.447
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.342
_exptl_absorpt_correction_T_min  0.9231
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrysAlis v171.33.42'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.453
_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         0.209
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.040(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   0.954
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2075
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.023
_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          0.0664
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1409
_reflns_number_total             2075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lo5078sup1.cif
_cod_data_source_block           m295
_cod_depositor_comments
'Adding full bibliography for 2108742--2108745.cif.'
_cod_original_formula_sum        'C7.50 H10 N3 O4'
_cod_database_code               2108744
_cod_database_fobs_code          2108744
_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 0.22212(8) 0.42410(6) 0.38827(6) 0.02018(16) Uani 1 1 d . . . . .
O2 O 0.21602(8) 0.17159(6) 0.16260(6) 0.02048(16) Uani 1 1 d . . . . .
O3 O 0.33476(9) 0.14770(7) 0.65186(6) 0.02495(16) Uani 1 1 d . . . . .
O4 O 0.08683(9) 0.05846(7) 0.42720(6) 0.02665(16) Uani 1 1 d . . . . .
C1 C 0.26733(11) 0.26707(9) 0.31725(8) 0.0155(2) Uani 1 1 d . . . . .
C2 C 0.38797(12) 0.19357(10) 0.42455(8) 0.0180(2) Uani 1 1 d . . . . .
C3 C 0.26441(12) 0.13113(9) 0.51245(9) 0.0177(2) Uani 1 1 d . . . . .
N1A1 N 0.29157(10) 0.62663(8) 0.71732(7) 0.01724(18) Uani 1 1 d . . . . .
C1A C 0.23138(12) 0.78757(10) 0.78761(8) 0.0170(2) Uani 1 1 d . . . . .
N1A2 N 0.29976(9) 0.85671(8) 0.95151(7) 0.01723(18) Uani 1 1 d . . . . .
C2A C 0.40650(12) 0.73568(10) 0.98599(9) 0.0190(2) Uani 1 1 d . . . . .
C3A C 0.40074(12) 0.59229(10) 0.83979(8) 0.0189(2) Uani 1 1 d . . . . .
N1B1 N 0.07017(19) 0.40799(15) 1.04968(14) 0.0176(4) Uani 0.5 1 d D . P . .
C1B C 0.0044(2) 0.37842(18) 0.89125(17) 0.0172(4) Uani 0.5 1 d . . P . .
N1B2 N -0.06198(19) 0.52515(15) 0.89252(14) 0.0167(4) Uani 0.5 1 d D . P . .
C2B C -0.0381(2) 0.65397(19) 1.05460(17) 0.0185(4) Uani 0.5 1 d . . P . .
C3B C 0.0433(2) 0.57945(18) 1.15059(17) 0.0169(4) Uani 0.5 1 d . . P . .
H1A1 H 0.2673(13) 0.5516(11) 0.6025(10) 0.045(3) Uiso 1 1 d . . . . .
H1A H 0.1507(11) 0.8489(9) 0.7294(8) 0.023(2) Uiso 1 1 d . . . . .
H1A2 H 0.2797(13) 0.9704(11) 1.0365(10) 0.048(3) Uiso 1 1 d . . . . .
H2A H 0.4681(11) 0.7614(9) 1.0963(8) 0.022(2) Uiso 1 1 d . . . . .
H3A H 0.4555(11) 0.4870(9) 0.8168(8) 0.020(2) Uiso 1 1 d . . . . .
H3B H 0.080(2) 0.6253(18) 1.2761(15) 0.016(4) Uiso 0.5 1 d . . P . .
H2B H -0.073(2) 0.753(2) 1.0707(17) 0.028(5) Uiso 0.5 1 d . . P . .
H1B2 H -0.116(3) 0.535(2) 0.7899(17) 0.042(5) Uiso 0.5 1 d D . P . .
H1B1 H 0.125(3) 0.3191(19) 1.0916(18) 0.045(6) Uiso 0.5 1 d D . P . .
H1B H 0.008(3) 0.273(2) 0.790(2) 0.058(6) Uiso 0.5 1 d . . P . .
H4 H 0.0000 0.0000 0.5000 0.094(6) Uiso 1 2 d S . P . .
H21 H 0.4913(11) 0.2850(9) 0.5048(8) 0.022(2) Uiso 1 1 d . . . . .
H22 H 0.4485(11) 0.0872(9) 0.3550(8) 0.023(2) 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 111.61(6) . . ?
O2 C1 O1 122.34(8) . . ?
O2 C1 C2 119.52(7) . . ?
O1 C1 C2 118.14(6) . . ?
C1 C2 C3 112.59(7) . . ?
C1 C2 H21 108.5(5) . . ?
C3 C2 H21 109.9(5) . . ?
C1 C2 H22 110.5(4) . . ?
C3 C2 H22 106.6(5) . . ?
H21 C2 H22 108.7(6) . . ?
O3 C3 O4 124.59(9) . . ?
O3 C3 C2 120.51(7) . . ?
O4 C3 C2 114.89(7) . . ?
C1A N1A1 C3A 109.05(6) . . ?
C1A N1A1 H1A1 125.0(6) . . ?
C3A N1A1 H1A1 125.9(6) . . ?
N1A2 C1A N1A1 107.96(8) . . ?
N1A2 C1A H1A 125.0(4) . . ?
N1A1 C1A H1A 127.0(4) . . ?
C1A N1A2 C2A 108.79(7) . . ?
C1A N1A2 H1A2 128.0(6) . . ?
C2A N1A2 H1A2 123.2(6) . . ?
C3A C2A N1A2 107.10(7) . . ?
C3A C2A H2A 131.5(5) . . ?
N1A2 C2A H2A 121.4(5) . . ?
C2A C3A N1A1 107.10(7) . . ?
C2A C3A H3A 130.3(4) . . ?
N1A1 C3A H3A 122.6(4) . . ?
N1B2 N1B1 C2B 146.1(3) 2_567 2_567 ?
N1B2 N1B1 C1B 122.8(2) 2_567 . ?
C2B N1B1 C1B 24.32(14) 2_567 . ?
N1B2 N1B1 C3B 16.07(19) 2_567 . ?
C2B N1B1 C3B 131.4(2) 2_567 . ?
C1B N1B1 C3B 107.46(13) . . ?
N1B2 N1B1 C1B 36.24(19) 2_567 2_567 ?
C2B N1B1 C1B 110.67(18) 2_567 2_567 ?
C1B N1B1 C1B 86.75(11) . 2_567 ?
C3B N1B1 C1B 20.77(8) . 2_567 ?
N1B2 N1B1 C3B 109.3(2) 2_567 2_567 ?
C2B N1B1 C3B 37.58(14) 2_567 2_567 ?
C1B N1B1 C3B 13.57(8) . 2_567 ?
C3B N1B1 C3B 93.97(11) . 2_567 ?
C1B N1B1 C3B 73.23(9) 2_567 2_567 ?
N1B2 N1B1 H1B1 108.7(8) 2_567 . ?
C2B N1B1 H1B1 103.8(8) 2_567 . ?
C1B N1B1 H1B1 128.1(8) . . ?
C3B N1B1 H1B1 124.4(8) . . ?
C1B N1B1 H1B1 144.9(8) 2_567 . ?
C3B N1B1 H1B1 141.4(7) 2_567 . ?
C2B C1B C3B 166.4(3) 2_567 2_567 ?
C2B C1B N1B2 139.0(2) 2_567 . ?
C3B C1B N1B2 30.51(13) 2_567 . ?
C2B C1B N1B1 30.98(14) 2_567 . ?
C3B C1B N1B1 138.6(2) 2_567 . ?
N1B2 C1B N1B1 108.54(12) . . ?
C2B C1B N1B2 47.25(15) 2_567 2_567 ?
C3B C1B N1B2 122.04(18) 2_567 2_567 ?
N1B2 C1B N1B2 92.00(11) . 2_567 ?
N1B1 C1B N1B2 16.60(7) . 2_567 ?
C2B C1B N1B1 123.66(19) 2_567 2_567 ?
C3B C1B N1B1 45.58(14) 2_567 2_567 ?
N1B2 C1B N1B1 15.36(7) . 2_567 ?
N1B1 C1B N1B1 93.25(11) . 2_567 ?
N1B2 C1B N1B1 76.67(8) 2_567 2_567 ?
C2B C1B H1B 98.2(13) 2_567 . ?
C3B C1B H1B 92.7(13) 2_567 . ?
N1B2 C1B H1B 122.7(13) . . ?
N1B1 C1B H1B 128.6(13) . . ?
N1B2 C1B H1B 145.2(13) 2_567 . ?
N1B1 C1B H1B 138.1(13) 2_567 . ?
N1B1 N1B2 C3B 152.3(3) 2_567 2_567 ?
N1B1 N1B2 C1B 128.4(2) 2_567 . ?
C3B N1B2 C1B 25.04(13) 2_567 . ?
N1B1 N1B2 C2B 19.99(18) 2_567 . ?
C3B N1B2 C2B 133.80(19) 2_567 . ?
C1B N1B2 C2B 109.04(13) . . ?
N1B1 N1B2 C1B 40.56(18) 2_567 2_567 ?
C3B N1B2 C1B 112.68(17) 2_567 2_567 ?
C1B N1B2 C1B 88.00(11) . 2_567 ?
C2B N1B2 C1B 21.12(9) . 2_567 ?
N1B1 N1B2 C2B 114.8(2) 2_567 2_567 ?
C3B N1B2 C2B 38.32(13) 2_567 2_567 ?
C1B N1B2 C2B 13.59(8) . 2_567 ?
C2B N1B2 C2B 95.56(11) . 2_567 ?
C1B N1B2 C2B 74.47(9) 2_567 2_567 ?
N1B1 N1B2 H1B2 108.7(9) 2_567 . ?
C3B N1B2 H1B2 97.9(9) 2_567 . ?
C1B N1B2 H1B2 122.7(9) . . ?
C2B N1B2 H1B2 128.2(9) . . ?
C1B N1B2 H1B2 149.3(9) 2_567 . ?
C2B N1B2 H1B2 136.2(9) 2_567 . ?
C1B C2B N1B1 124.7(2) 2_567 2_567 ?
C1B C2B C3B 6.82(17) 2_567 . ?
N1B1 C2B C3B 119.91(19) 2_567 . ?
C1B C2B N1B2 111.6(2) 2_567 . ?
N1B1 C2B N1B2 13.89(12) 2_567 . ?
C3B C2B N1B2 106.46(13) . . ?
C1B C2B N1B2 27.39(15) 2_567 2_567 ?
N1B1 C2B N1B2 97.86(16) 2_567 2_567 ?
C3B C2B N1B2 22.05(7) . 2_567 ?
N1B2 C2B N1B2 84.44(11) . 2_567 ?
C1B C2B C3B 94.77(18) 2_567 2_567 ?
N1B1 C2B C3B 30.37(13) 2_567 2_567 ?
C3B C2B C3B 89.64(11) . 2_567 ?
N1B2 C2B C3B 16.85(8) . 2_567 ?
N1B2 C2B C3B 67.61(8) 2_567 2_567 ?
C1B C2B H2B 130.6(10) 2_567 . ?
N1B1 C2B H2B 104.1(10) 2_567 . ?
C3B C2B H2B 135.9(10) . . ?
N1B2 C2B H2B 117.6(10) . . ?
N1B2 C2B H2B 157.9(10) 2_567 . ?
C3B C2B H2B 134.5(10) 2_567 . ?
C1B C3B N1B2 124.4(2) 2_567 2_567 ?
C1B C3B C2B 6.79(17) 2_567 . ?
N1B2 C3B C2B 119.63(17) 2_567 . ?
C1B C3B N1B1 113.65(19) 2_567 . ?
N1B2 C3B N1B1 11.62(13) 2_567 . ?
C2B C3B N1B1 108.49(12) . . ?
C1B C3B N1B1 27.79(14) 2_567 2_567 ?
N1B2 C3B N1B1 97.12(15) 2_567 2_567 ?
C2B C3B N1B1 22.51(7) . 2_567 ?
N1B1 C3B N1B1 86.03(11) . 2_567 ?
C1B C3B C2B 95.46(17) 2_567 2_567 ?
N1B2 C3B C2B 29.35(12) 2_567 2_567 ?
C2B C3B C2B 90.36(11) . 2_567 ?
N1B1 C3B C2B 18.19(8) . 2_567 ?
N1B1 C3B C2B 67.87(8) 2_567 2_567 ?
C1B C3B H3B 127.0(9) 2_567 . ?
N1B2 C3B H3B 107.7(9) 2_567 . ?
C2B C3B H3B 132.5(9) . . ?
N1B1 C3B H3B 119.0(9) . . ?
N1B1 C3B H3B 154.8(9) 2_567 . ?
C2B C3B H3B 137.0(9) 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 1.2645(10) . ?
O2 C1 1.2549(9) . ?
O3 C3 1.2251(10) . ?
O4 C3 1.2965(11) . ?
O4 H4 1.2269(7) . ?
C1 C2 1.5166(12) . ?
C2 C3 1.5229(13) . ?
C2 H21 0.958(6) . ?
C2 H22 1.001(7) . ?
N1A1 C1A 1.3326(11) . ?
N1A1 C3A 1.3764(11) . ?
N1A1 H1A1 0.938(8) . ?
C1A N1A2 1.3312(10) . ?
C1A H1A 1.003(8) . ?
N1A2 C2A 1.3826(11) . ?
N1A2 H1A2 0.964(8) . ?
C2A C3A 1.3433(11) . ?
C2A H2A 0.945(7) . ?
C3A H3A 0.923(7) . ?
N1B1 N1B2 0.5920(15) 2_567 ?
N1B1 C2B 0.8432(17) 2_567 ?
N1B1 C1B 1.347(2) . ?
N1B1 C3B 1.3655(18) . ?
N1B1 C1B 1.751(2) 2_567 ?
N1B1 C3B 1.909(2) 2_567 ?
N1B1 H1B1 1.030(17) . ?
C1B C2B 0.675(2) 2_567 ?
C1B C3B 0.678(2) 2_567 ?
C1B N1B2 1.321(2) . ?
C1B N1B2 1.7405(19) 2_567 ?
C1B N1B1 1.751(2) 2_567 ?
C1B H1B 0.969(16) . ?
N1B2 N1B1 0.5919(15) 2_567 ?
N1B2 C3B 0.8134(18) 2_567 ?
N1B2 C2B 1.3749(18) . ?
N1B2 C1B 1.7404(19) 2_567 ?
N1B2 C2B 1.883(2) 2_567 ?
N1B2 H1B2 0.985(16) . ?
C2B C1B 0.675(2) 2_567 ?
C2B N1B1 0.8432(17) 2_567 ?
C2B C3B 1.343(2) . ?
C2B N1B2 1.883(2) 2_567 ?
C2B C3B 2.025(2) 2_567 ?
C2B H2B 0.825(16) . ?
C3B C1B 0.678(2) 2_567 ?
C3B N1B2 0.8134(18) 2_567 ?
C3B N1B1 1.909(2) 2_567 ?
C3B C2B 2.025(2) 2_567 ?
C3B H3B 1.018(13) . ?
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 1.2269(7) 2.4481(12) 3.1641(13) 114.73(3) 2_556
O4 H4 O4 1.2269(7) 1.2269(7) 2.4538(14) 180.000(0) 2_556
C2 H21 O1 0.958(6) 2.797(7) 3.6814(19) 153.9(7) 2_666
C2 H22 O3 1.001(7) 2.496(8) 3.3796(15) 147.0(6) 2_656
N1A1 H1A1 O1 0.938(8) 1.735(8) 2.6715(13) 176.6(10) .
C1A H1A O4 1.003(8) 2.352(8) 3.3408(14) 168.3(6) 2_566
N1A2 H1A2 O2 0.964(8) 1.702(8) 2.6583(13) 171.0(8) 1_566
C2A H2A O3 0.945(7) 2.231(7) 3.1613(15) 167.8(7) 2_667
C3A H3A O3 0.923(7) 2.586(7) 3.3199(15) 136.9(6) .
C3B H3B O1 1.018(13) 2.473(16) 3.0957(19) 118.8(10) 1_556
C2B H2B O2 0.825(16) 2.534(17) 3.065(2) 123.2(11) 2_566
C2B H2B O4 0.825(16) 3.094(12) 3.525(2) 115.2(11) 1_566
N1B2 H1B2 O1 0.985(16) 1.844(16) 2.8261(16) 174.1(13) 2_566
N1B2 H1B2 O2 0.985(16) 2.448(17) 2.9903(17) 114.2(10) 2_566
N1B1 H1B1 O1 1.030(17) 2.412(15) 3.0330(16) 117.8(9) 1_556
N1B1 H1B1 O2 1.030(17) 1.719(17) 2.7492(17) 179.7(14) 1_556
C1B H1B O3 0.969(16) 2.824(19) 3.516(2) 129.0(13) .
C1B H1B O4 0.969(16) 2.576(16) 3.476(2) 154.4(17) 2_556
