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_7250466
_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         'C15 H18 N, C4 H3 O4'
_chemical_formula_sum            'C19 H21 N O4'
_chemical_formula_weight         327.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6443(5)
_cell_length_b                   17.2728(14)
_cell_length_c                   17.5092(15)
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.50
_cell_measurement_theta_min      3.59
_cell_volume                     1707.0(3)
_computing_cell_refinement       'Bruker Apex6, 2024'
_computing_data_collection       'Bruker Apex6, 2024'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_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, 2019)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_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  0.0519
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19608
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.497
_diffrn_reflns_theta_min         3.594
_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    0.729
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1728 before and 0.0959 after correction.
The Ratio of minimum to maximum transmission is 0.6877.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0550P)^2^+0.4062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                3064
_reflns_number_total             3071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00380f2.cif
_cod_data_source_block           1_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7250461--7250466.cif.'
_cod_database_code               7250466
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.795
_shelx_estimated_absorpt_t_min   0.721
_diffrn_oxdiff_ac3_digest_hkl    41149d86946decd5adcee6733c3c12fd22d7e3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(3)
 0.1(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 N8-H8b = N8-H8a
 0.93 with sigma of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C9(H9a,H9b), C10(H10a,H10b)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C4A(H4A), C5A(H5A)
;
_shelx_res_checksum              79121
_olex2_exptl_crystal_mounting_method
'cryoloop, covered with Parabar 10320 (formerly known as Paratone)'
_olex2_submission_special_instructions 'No special instructions were received'