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_7250463
_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         'C8 H14 N2, 3(H2 O), 2(C4 H3 O4)'
_chemical_formula_sum            'C16 H26 N2 O11'
_chemical_formula_weight         422.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-01 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.675(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0431(7)
_cell_length_b                   14.8328(12)
_cell_length_c                   16.9537(14)
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.10
_cell_measurement_theta_min      5.78
_cell_volume                     1999.5(3)
_computing_cell_refinement       'Bruker Apex5, 2024'
_computing_data_collection       'Bruker Apex5, 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, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_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  0.0508
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21289
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_min         5.278
_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    1.029
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1472 before and 0.0861 after correction.
The Ratio of minimum to maximum transmission is 0.5997.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.0079(11)
_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   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1120P)^2^+1.0225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3477
_reflns_number_total             3612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00380f2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7250461--7250466.cif.'
_cod_database_code               7250463
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.721
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O8B-H8B = N10-H10A = N10-H10C = N10-H10B = O8A-H8A = N1-H1A = N1-H1C = N1-H1B
 1.05 with sigma of 0.02
 O2W-H2WA
 1.05 with sigma of 0.02
 O3W-H3WA = O3W-H3WB
 1.05 with sigma of 0.02
 O1W-H1WA = O1W-H1WB
 1.05 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B)
;
_shelx_res_checksum              95871
_olex2_exptl_crystal_mounting_method
'cryoloop, covered with Parabar 10320 (formerly known as Paratone)'
_olex2_submission_special_instructions 'No special instructions were received'