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_7250465
_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, 2(C2 H1.5 O2)'
_chemical_formula_sum            'C19 H21 N O4'
_chemical_formula_weight         327.37
_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             2025-02-26
_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                76.150(5)
_cell_angle_beta                 75.668(5)
_cell_angle_gamma                72.689(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9935(7)
_cell_length_b                   10.9224(10)
_cell_length_c                   11.3553(10)
_cell_measurement_reflns_used    6343
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.07
_cell_measurement_theta_min      4.08
_cell_volume                     902.21(14)
_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, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_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_unetI/netI     0.0897
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12640
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.096
_diffrn_reflns_theta_min         4.084
_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    0.690
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1198 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.7572.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         12640
_refine_ls_number_restraints     496
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0908
_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^)+(0.1329P)^2^+0.9044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2727
_refine_ls_wR_factor_ref         0.2846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10052
_reflns_number_total             12640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00380f2.cif
_cod_data_source_block           1_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7250461--7250466.cif.'
_cod_database_code               7250465
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.858
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.524(12)
 0.476(12)
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
 C11-C12' \\sim C11-C12
 with sigma of 0.02
 C11-C16' \\sim C11-C16
 with sigma of 0.02
 C13'-C12' \\sim C13-C12
 with sigma of 0.02
 C13'-C14' \\sim C13-C14
 with sigma of 0.02
 C16'-C15' \\sim C16-C15
 with sigma of 0.02
 C14'-C15' \\sim C14-C15
 with sigma of 0.02
 C11-C13' \\sim C11-C13
 with sigma of 0.04
 C11-C15' \\sim C11-C15
 with sigma of 0.04
 C13'-C15' \\sim C13-C15
 with sigma of 0.04
 C12'-C14' \\sim C12-C14
 with sigma of 0.04
 C16'-C14' \\sim C16-C14
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12' \\sim C13' \\sim C14' \\sim C15' \\sim C16' \\sim C12
\\sim C13 \\sim C14 \\sim C15 \\sim C16: within 5A with sigma of 0.002 and
sigma for terminal atoms of 0.004 within 5A
5. Rigid body (RIGU) restrains
 C10, C11, C12', C13', C14', C15', C16'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C10, C11, C12, C13, C14, C15, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=
 Sof(C16)=Sof(H16)=1-FVAR(1)
 Sof(C12')=Sof(H12')=Sof(C13')=Sof(H13')=Sof(C14')=Sof(H14')=Sof(C15')=
 Sof(H15')=Sof(C16')=Sof(H16')=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12'(H12'), C13'(H13'), C14'(H14'),
 C15'(H15'), C16'(H16'), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C8A(H8AA), C4A(H4A)
;
_shelx_res_checksum              29650
_olex2_exptl_crystal_mounting_method
'cryoloop, covered with Parabar 10320 (formerly known as Paratone)'
_olex2_submission_special_instructions 'No special instructions were received'