Negative thermal expansion and linear compressibility in 1H-imidazol-3-ium 2-hydroxybenzoate with a helical network of hydrogen bonds
Zieba, Sylwia; Dubis, Alina Teresa; Rusek, Michalina; Katrusiak, Andrzej; Gzella, Andrzej K.; Lapinski, Andrzej; Physical Chemistry Chemical Physics  (2025) –; doi:10.1039/D4CP04519J

data_7250190
_publ_section_title
;
 Negative thermal expansion and linear compressibility in
 1H-imidazol-3-ium 2-hydroxybenzoate with a helical network of hydrogen
 bonds
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D4CP04519J
_journal_year                    2025
_chemical_formula_moiety         'C7 H5 O3, C3 H5 N2'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-05-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-05-16 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.540(5)
_cell_length_b                   10.49(4)
_cell_length_c                   14.153(8)
_cell_measurement_pressure       2270000(2)
_cell_measurement_reflns_used    581
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.269
_cell_measurement_theta_min      4.956
_cell_volume                     1713(7)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.337
_diffrn_measured_fraction_theta_max 0.299
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_Laue_measured_fraction_full 0.337
_diffrn_reflns_Laue_measured_fraction_max 0.299
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5289
_diffrn_reflns_point_group_measured_fraction_full 0.337
_diffrn_reflns_point_group_measured_fraction_max 0.299
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.269
_diffrn_reflns_theta_min         4.956
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Data were collected at room temperature and pressure of 2.27(2) GPa
 (2270000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.044
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         576
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.2344
_refine_ls_R_factor_gt           0.0968
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1859P)^2^+1.9547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2490
_refine_ls_wR_factor_ref         0.3807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                189
_reflns_number_total             576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cp04519j2.cif
_cod_data_source_block           227GPa
_cod_database_code               7250190
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 H3A-O2
 1.9 with sigma of 0.01
 H3A-C8_$1
 2.6 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of
0.004 and sigma for terminal atoms of 0.008
Uanis(C7) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.004 and sigma
for terminal atoms of 0.008
Uanis(O3) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C8) \\sim
Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
Uanis(N1) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(N2) \\sim
Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(N1) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
4.a :
 N1(C8,N2,C10,C9)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), N1(H1), C8(H8), N2(H2), C10(H10), C9(H9)
4.c Fitted hexagon refined as free rotating group:
 C2(C3,C4,C5,C6,C1)
4.d Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;