#------------------------------------------------------------------------------
#$Date: 2021-02-05 16:52:16 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/87/2108745.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_2108745
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                115.79(3)
_cell_angle_beta                 103.12(3)
_cell_angle_gamma                91.91(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2950(10)
_cell_length_b                   8.280(2)
_cell_length_c                   9.249(2)
_cell_measurement_reflns_used    4538
_cell_measurement_temperature    330(2)
_cell_measurement_theta_max      56.12
_cell_measurement_theta_min      4
_cell_volume                     484.3(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      330(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.922
_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  0.0929
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4534
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.088
_diffrn_reflns_theta_min         2.900
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.253
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrysAlis v171.33.42'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_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         0.171
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.114(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   1.089
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2174
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.085
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0250P)²+0.0250P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1217
_reflns_number_total             2174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lo5078sup1.cif
_cod_data_source_block           m330
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 2108742--2108745.cif.
;
_cod_original_formula_sum        'C7.50 H10 N3 O4'
_cod_database_code               2108745
_cod_database_fobs_code          2108745
_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 0.22508(10) 0.42168(8) 0.39009(7) 0.0560(2) Uani 1 1 d . . . . .
O2 O 0.21472(10) 0.17168(8) 0.16536(7) 0.0579(2) Uani 1 1 d . . . . .
O3 O 0.32732(10) 0.14313(10) 0.65214(7) 0.0731(3) Uani 1 1 d . . . . .
O4 O 0.08773(10) 0.05745(10) 0.42937(7) 0.0796(2) Uani 1 1 d . . . . .
C1 C 0.26420(12) 0.26448(11) 0.31948(9) 0.0405(3) Uani 1 1 d . . . . .
C2 C 0.37857(13) 0.18846(13) 0.42750(10) 0.0504(3) Uani 1 1 d . . . . .
C3 C 0.26036(14) 0.12818(11) 0.51478(10) 0.0463(3) Uani 1 1 d . . . . .
N1A1 N 0.29127(11) 0.63347(10) 0.71905(8) 0.0469(2) Uani 1 1 d . . . . .
C1A C 0.23064(13) 0.79029(12) 0.78717(10) 0.0477(3) Uani 1 1 d . . . . .
N1A2 N 0.29507(10) 0.86033(10) 0.94957(8) 0.0474(2) Uani 1 1 d . . . . .
C2A C 0.40044(14) 0.74436(13) 0.98708(10) 0.0528(3) Uani 1 1 d . . . . .
C3A C 0.39871(14) 0.60284(13) 0.84372(11) 0.0543(3) Uani 1 1 d . . . . .
N1B1 N 0.0687(2) 0.40947(19) 1.05048(17) 0.0480(5) Uani 0.5 1 d D . P A 1
C1B C 0.0063(3) 0.3815(3) 0.8943(2) 0.0579(7) Uani 0.5 1 d . . P A 1
N1B2 N -0.0627(2) 0.5243(2) 0.89244(16) 0.0492(5) Uani 0.5 1 d D . P A 1
C2B C -0.0367(3) 0.6520(3) 1.0521(2) 0.0566(7) Uani 0.5 1 d . . P A 1
C3B C 0.0488(3) 0.5830(3) 1.1552(2) 0.0577(7) Uani 0.5 1 d . . P A 1
H3B H 0.071(2) 0.627(2) 1.2757(18) 0.048(5) Uiso 0.5 1 d . . P B 1
H2B H -0.075(2) 0.754(2) 1.0758(17) 0.043(5) Uiso 0.5 1 d . . P C 1
H1B2 H -0.112(2) 0.558(2) 0.7997(18) 0.065(6) Uiso 0.5 1 d D . P D 1
H1B1 H 0.120(3) 0.309(2) 1.080(2) 0.106(8) Uiso 0.5 1 d D . P E 1
H1B H 0.002(3) 0.279(3) 0.801(2) 0.083(7) Uiso 0.5 1 d . . P F 1
H4 H 0.0000 0.0000 0.5000 0.114(6) Uiso 1 2 d S . P . .
H21 H 0.4814(13) 0.2835(12) 0.5116(11) 0.071(3) Uiso 1 1 d . . . . .
H22 H 0.4276(12) 0.0860(12) 0.3566(10) 0.066(3) Uiso 1 1 d . . . . .
H1A1 H 0.2716(12) 0.5577(12) 0.6055(10) 0.070(3) Uiso 1 1 d . . . . .
H1A H 0.1536(13) 0.8459(13) 0.7297(11) 0.073(3) Uiso 1 1 d . . . . .
H1A2 H 0.2770(12) 0.9651(12) 1.0323(11) 0.071(3) Uiso 1 1 d . . . . .
H2A H 0.4578(13) 0.7779(12) 1.0997(10) 0.066(3) Uiso 1 1 d . . . . .
H3A H 0.4503(14) 0.5055(14) 0.8252(12) 0.090(4) 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 112.83(7) . . ?
O2 C1 O1 122.29(9) . . ?
O2 C1 C2 119.66(8) . . ?
O1 C1 C2 118.05(7) . . ?
C3 C2 C1 112.56(8) . . ?
C3 C2 H21 108.6(6) . . ?
C1 C2 H21 108.0(7) . . ?
C3 C2 H22 109.0(6) . . ?
C1 C2 H22 107.6(6) . . ?
H21 C2 H22 111.1(7) . . ?
O3 C3 O4 123.83(10) . . ?
O3 C3 C2 121.38(9) . . ?
O4 C3 C2 114.77(8) . . ?
C1A N1A1 C3A 108.34(8) . . ?
C1A N1A1 H1A1 126.8(7) . . ?
C3A N1A1 H1A1 124.7(6) . . ?
N1A2 C1A N1A1 108.80(9) . . ?
N1A2 C1A H1A 124.7(5) . . ?
N1A1 C1A H1A 126.5(5) . . ?
C1A N1A2 C2A 108.53(8) . . ?
C1A N1A2 H1A2 130.9(6) . . ?
C2A N1A2 H1A2 120.5(7) . . ?
C3A C2A N1A2 107.37(9) . . ?
C3A C2A H2A 134.5(6) . . ?
N1A2 C2A H2A 118.1(6) . . ?
C2A C3A N1A1 106.96(9) . . ?
C2A C3A H3A 130.0(7) . . ?
N1A1 C3A H3A 123.0(7) . . ?
N1B2 N1B1 C2B 146.7(4) 2_567 2_567 ?
N1B2 N1B1 C1B 123.2(3) 2_567 . ?
C2B N1B1 C1B 24.69(19) 2_567 . ?
N1B2 N1B1 C3B 15.0(2) 2_567 . ?
C2B N1B1 C3B 133.3(3) 2_567 . ?
C1B N1B1 C3B 108.98(18) . . ?
N1B2 N1B1 C1B 36.9(2) 2_567 2_567 ?
C2B N1B1 C1B 110.4(2) 2_567 2_567 ?
C1B N1B1 C1B 86.35(14) . 2_567 ?
C3B N1B1 C1B 22.97(11) . 2_567 ?
N1B2 N1B1 C3B 110.4(3) 2_567 2_567 ?
C2B N1B1 C3B 36.83(19) 2_567 2_567 ?
C1B N1B1 C3B 13.00(11) . 2_567 ?
C3B N1B1 C3B 96.46(13) . 2_567 ?
C1B N1B1 C3B 73.65(11) 2_567 2_567 ?
N1B2 N1B1 H1B1 114.5(11) 2_567 . ?
C2B N1B1 H1B1 97.5(10) 2_567 . ?
C1B N1B1 H1B1 122.0(11) . . ?
C3B N1B1 H1B1 129.0(11) . . ?
C1B N1B1 H1B1 151.2(11) 2_567 . ?
C3B N1B1 H1B1 134.3(10) 2_567 . ?
C2B C1B C3B 164.2(5) 2_567 2_567 ?
C2B C1B N1B2 139.3(3) 2_567 . ?
C3B C1B N1B2 34.28(19) 2_567 . ?
C2B C1B N1B1 31.18(19) 2_567 . ?
C3B C1B N1B1 142.1(3) 2_567 . ?
N1B2 C1B N1B1 109.22(15) . . ?
C2B C1B N1B2 47.4(2) 2_567 2_567 ?
C3B C1B N1B2 125.7(3) 2_567 2_567 ?
N1B2 C1B N1B2 92.65(14) . 2_567 ?
N1B1 C1B N1B2 16.57(9) . 2_567 ?
C2B C1B N1B1 123.9(3) 2_567 2_567 ?
C3B C1B N1B1 49.5(2) 2_567 2_567 ?
N1B2 C1B N1B1 15.58(8) . 2_567 ?
N1B1 C1B N1B1 93.65(14) . 2_567 ?
N1B2 C1B N1B1 77.08(11) 2_567 2_567 ?
C2B C1B H1B 96.3(16) 2_567 . ?
C3B C1B H1B 89.5(15) 2_567 . ?
N1B2 C1B H1B 123.4(15) . . ?
N1B1 C1B H1B 127.3(16) . . ?
N1B2 C1B H1B 143.7(16) 2_567 . ?
N1B1 C1B H1B 138.9(15) 2_567 . ?
N1B1 N1B2 C3B 154.5(4) 2_567 2_567 ?
N1B1 N1B2 C1B 127.6(3) 2_567 . ?
C3B N1B2 C1B 28.86(17) 2_567 . ?
N1B1 N1B2 C2B 19.6(2) 2_567 . ?
C3B N1B2 C2B 136.5(3) 2_567 . ?
C1B N1B2 C2B 108.37(16) . . ?
N1B1 N1B2 C1B 40.2(2) 2_567 2_567 ?
C3B N1B2 C1B 115.3(2) 2_567 2_567 ?
C1B N1B2 C1B 87.35(14) . 2_567 ?
C2B N1B2 C1B 21.27(12) . 2_567 ?
N1B1 N1B2 C2B 114.2(3) 2_567 2_567 ?
C3B N1B2 C2B 41.54(18) 2_567 2_567 ?
C1B N1B2 C2B 13.51(10) . 2_567 ?
C2B N1B2 C2B 95.19(14) . 2_567 ?
C1B N1B2 C2B 74.04(11) 2_567 2_567 ?
N1B1 N1B2 H1B2 100.0(9) 2_567 . ?
C3B N1B2 H1B2 104.7(9) 2_567 . ?
C1B N1B2 H1B2 132.3(9) . . ?
C2B N1B2 H1B2 118.8(9) . . ?
C1B N1B2 H1B2 140.0(9) 2_567 . ?
C2B N1B2 H1B2 145.8(9) 2_567 . ?
C1B C2B N1B1 124.1(3) 2_567 2_567 ?
C1B C2B N1B2 111.3(3) 2_567 . ?
N1B1 C2B N1B2 13.70(16) 2_567 . ?
C1B C2B C3B 8.1(2) 2_567 . ?
N1B1 C2B C3B 121.8(3) 2_567 . ?
N1B2 C2B C3B 108.40(18) . . ?
C1B C2B N1B2 27.2(2) 2_567 2_567 ?
N1B1 C2B N1B2 98.1(2) 2_567 2_567 ?
N1B2 C2B N1B2 84.81(14) . 2_567 ?
C3B C2B N1B2 23.68(9) . 2_567 ?
C1B C2B C3B 95.2(3) 2_567 2_567 ?
N1B1 C2B C3B 29.49(17) 2_567 2_567 ?
N1B2 C2B C3B 16.19(11) . 2_567 ?
C3B C2B C3B 92.32(14) . 2_567 ?
N1B2 C2B C3B 68.68(10) 2_567 2_567 ?
C1B C2B H2B 125.8(11) 2_567 . ?
N1B1 C2B H2B 108.4(10) 2_567 . ?
N1B2 C2B H2B 122.0(10) . . ?
C3B C2B H2B 129.6(11) . . ?
N1B2 C2B H2B 152.9(11) 2_567 . ?
C3B C2B H2B 137.9(10) 2_567 . ?
C1B C3B N1B2 116.9(3) 2_567 2_567 ?
C1B C3B C2B 7.7(2) 2_567 . ?
N1B2 C3B C2B 114.8(2) 2_567 . ?
C1B C3B N1B1 107.6(2) 2_567 . ?
N1B2 C3B N1B1 10.54(16) 2_567 . ?
C2B C3B N1B1 104.91(16) . . ?
C1B C3B N1B1 24.94(19) 2_567 2_567 ?
N1B2 C3B N1B1 93.41(19) 2_567 2_567 ?
C2B C3B N1B1 21.38(9) . 2_567 ?
N1B1 C3B N1B1 83.54(13) . 2_567 ?
C1B C3B C2B 90.4(2) 2_567 2_567 ?
N1B2 C3B C2B 27.28(16) 2_567 2_567 ?
C2B C3B C2B 87.68(14) . 2_567 ?
N1B1 C3B C2B 17.24(10) . 2_567 ?
N1B1 C3B C2B 66.31(10) 2_567 2_567 ?
C1B C3B H3B 126.8(11) 2_567 . ?
N1B2 C3B H3B 112.2(11) 2_567 . ?
C2B C3B H3B 131.4(11) . . ?
N1B1 C3B H3B 122.6(11) . . ?
N1B1 C3B H3B 151.7(10) 2_567 . ?
C2B C3B H3B 139.3(11) 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 1.2538(11) . ?
O2 C1 1.2439(10) . ?
O3 C3 1.2022(11) . ?
O4 C3 1.2844(12) . ?
O4 H4 1.2258(8) . ?
C1 C2 1.5147(15) . ?
C2 C3 1.5107(16) . ?
C2 H21 0.975(8) . ?
C2 H22 0.959(9) . ?
N1A1 C1A 1.3158(12) . ?
N1A1 C3A 1.3659(13) . ?
N1A1 H1A1 0.932(8) . ?
C1A N1A2 1.3102(12) . ?
C1A H1A 0.951(11) . ?
N1A2 C2A 1.3606(14) . ?
N1A2 H1A2 0.912(8) . ?
C2A C3A 1.3307(13) . ?
C2A H2A 0.938(9) . ?
C3A H3A 0.866(12) . ?
N1B1 N1B2 0.5845(19) 2_567 ?
N1B1 C2B 0.828(2) 2_567 ?
N1B1 C1B 1.323(2) . ?
N1B1 C3B 1.375(2) . ?
N1B1 C1B 1.725(3) 2_567 ?
N1B1 C3B 1.930(3) 2_567 ?
N1B1 H1B1 1.04(2) . ?
C1B C2B 0.668(3) 2_567 ?
C1B C3B 0.706(3) 2_567 ?
C1B N1B2 1.305(3) . ?
C1B N1B2 1.715(2) 2_567 ?
C1B N1B1 1.725(3) 2_567 ?
C1B H1B 0.903(18) . ?
N1B2 N1B1 0.5845(19) 2_567 ?
N1B2 C3B 0.824(2) 2_567 ?
N1B2 C2B 1.355(2) . ?
N1B2 C1B 1.715(2) 2_567 ?
N1B2 C2B 1.863(3) 2_567 ?
N1B2 H1B2 1.008(18) . ?
C2B C1B 0.668(3) 2_567 ?
C2B N1B1 0.828(2) 2_567 ?
C2B C3B 1.361(3) . ?
C2B N1B2 1.863(3) 2_567 ?
C2B C3B 2.034(3) 2_567 ?
C2B H2B 0.847(16) . ?
C3B C1B 0.706(3) 2_567 ?
C3B N1B2 0.824(2) 2_567 ?
C3B N1B1 1.930(3) 2_567 ?
C3B C2B 2.034(3) 2_567 ?
C3B H3B 0.981(15) . ?
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 1.2258(8) 2.4333(12) 3.1675(14) 115.94(4) 2_556
O4 H4 O4 1.2258(8) 1.2258(9) 2.4516(17) 180.000(0) 2_556
C2 H21 O1 0.975(8) 2.865(9) 3.748(2) 151.2(8) 2_666
C2 H22 O3 0.959(9) 2.638(10) 3.4690(17) 145.1(7) 2_656
N1A1 H1A1 O1 0.932(8) 1.752(8) 2.6832(14) 177.0(9) .
C1A H1A O4 0.951(11) 2.418(11) 3.3578(16) 169.5(8) 2_566
N1A2 H1A2 O2 0.912(8) 1.767(9) 2.6698(14) 170.4(9) 1_566
C2A H2A O3 0.938(9) 2.269(9) 3.1796(17) 163.7(8) 2_667
C3A H3A O3 0.866(12) 2.713(10) 3.3882(18) 135.9(8) .
C3B H3B O1 0.981(15) 2.537(18) 3.087(3) 115.4(12) 1_556
C2B H2B O2 0.847(16) 2.570(17) 3.059(3) 117.9(12) 2_566
C2B H2B O4 0.847(16) 3.052(13) 3.526(3) 117.7(12) 1_566
N1B2 H1B2 O1 1.008(18) 1.845(17) 2.8425(19) 170.0(13) 2_566
N1B2 H1B2 O2 1.008(18) 2.297(18) 2.990(2) 124.9(11) 2_566
N1B1 H1B1 O1 1.04(2) 2.51(2) 3.0442(19) 111.2(12) 1_556
N1B1 H1B1 O2 1.04(2) 1.73(2) 2.754(2) 169.9(16) 1_556
C1B H1B O3 0.903(18) 3.02(2) 3.639(3) 127.5(15) .
C1B H1B O4 0.903(18) 2.609(18) 3.475(2) 161(2) 2_556
