Structural and computational analysis of H-bond mediated anion⋯anion interactions in new salts of fumaric and maleic acids
Jemai, Mahdi; Barceló-Oliver, Miquel; Marouani, Houda; Roisnel, Thierry; Frontera, Antonio; Prohens, Rafel; CrystEngComm 27 (2025) 4686–4698; doi:10.1039/D5CE00380F

data_7250462
_publ_section_title
;
 Structural and computational analysis of H-bond mediated
 anion&#x22EF;anion interactions in new salts of fumaric and maleic acids
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              4686
_journal_page_last               4698
_journal_paper_doi               10.1039/D5CE00380F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C10 H10 N, C4 H3 O4'
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.25
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-05
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-05-05 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                100.639(2)
_cell_angle_beta                 90.079(2)
_cell_angle_gamma                102.129(2)
_cell_formula_units_Z            2
_cell_length_a                   5.6275(3)
_cell_length_b                   9.6420(5)
_cell_length_c                   11.8288(6)
_cell_measurement_reflns_used    9803
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.81
_cell_volume                     616.18(6)
_computing_cell_refinement       'SAINT V8.41 (Bruker, 2016)'
_computing_data_collection       'Bruker Apex6, 2024'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2151
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.270
_diffrn_reflns_theta_min         5.519
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  0.753055
_exptl_absorpt_correction_T_min  0.508452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1154 before and 0.0724 after correction.
 The Ratio of minimum to maximum transmission is 0.68.

Final HKLF 4 output contains 44747 reflections, Rint = 0.0561
 (25096 with I > 3sig(I), Rint = 0.0521)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0561P)^2^+0.2238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2137
_reflns_number_total             2151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00380f2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7250461--7250466.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7250462
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.794
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C3A(H3A), C4A(H4A)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              14358
_olex2_exptl_crystal_mounting_method
'cryoloop, covered with Parabar 10320 (formerly known as Paratone)'
_olex2_submission_special_instructions 'No special instructions were received'