Tuning of a Hydrogen-Bonded Organic Framework by Liquid-Assisted Mechanosynthesis between Trans-Aconitic Acid and Isonicotinamide
Gogoi, Diptajyoti; Sasaki, Toshiyuki; Kalita, Nabadeep; Sethi, Tapaswini; Ichiyanagi, Kouhei; Nakane, Takanori; Kawamoto, Akihiro; Das, Dinabandhu; Kurisu, Genji; Thakuria, Ranjit; Chemistry A European Journal 31 (2025) e202403427(1)–e202403427(10); doi:10.1002/chem.202403427

data_3000561
_publ_section_title
;
 Tuning of a Hydrogen-Bonded Organic Framework by Liquid-Assisted
 Mechanosynthesis between Trans-Aconitic Acid and Isonicotinamide
;
_journal_name_full               'Chemistry A European Journal'
_journal_page_first              e202403427(1)
_journal_page_last               e202403427(10)
_journal_paper_doi               10.1002/chem.202403427
_journal_volume                  31
_journal_year                    2025
_chemical_formula_moiety         'C6 H6 O6, C6 H6 N2 O, 0.25(C7 H8)'
_chemical_formula_sum            'C13.75 H14 N2 O7'
_chemical_formula_weight         319.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-08-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 86.94
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.003
_cell_length_b                   15.214
_cell_length_c                   27.473
_cell_measurement_reflns_used    1404
_cell_measurement_temperature    79
_cell_measurement_theta_max      0.8023094206736104
_cell_measurement_theta_min      0.14236298594677577
_cell_volume                     2922.900
_computing_cell_refinement
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection
'Verlox (Thermo Fisher Scientific) and SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      79
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type
;
Talos Arctica G2
;
_diffrn_radiation_type           electrons
_diffrn_radiation_wavelength     0.02508
_diffrn_reflns_av_R_equivalents  0.3284
_diffrn_reflns_av_unetI/netI     0.4855
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25500
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        0.798
_diffrn_reflns_theta_max         0.798
_diffrn_reflns_theta_min         0.127
_exptl_absorpt_coefficient_mu    0.000
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       plate
_exptl_crystal_F_000             471
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       500(59)
_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   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         4016
_refine_ls_number_restraints     614
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.2627
_refine_ls_R_factor_gt           0.1540
_refine_ls_wR_factor_ref         0.3972
_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^)+(0.1694P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3759
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1128
_reflns_number_total             4016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            TACA-INA-Toluene_fill.cif
_cod_data_source_block           taca-ina-toluene
_cod_depositor_comments
'Releasing structure 3000561 into public domain as published material.'
_cod_original_cell_volume        2922.8
_cod_database_code               3000561
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups, All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C25-C31
 1.54 with sigma of 0.02
3. Restrained planarity
 C31, C25, C26, C27, C28, C29, C30
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.01
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O10) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(N1) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.005
Uanis(C24) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C27(0.5) H27(0.5) C26(0.5) H26(0.5) C25(0.5) C30(0.5) H30(0.5)
 C29(0.5) H29(0.5) C28(0.5) H28(0.5) C31(0.5) H31A(0.5) H31B(0.5) H31C(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C23(H23A,H23B)
7.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C11(H11A), C4(H4), C2(H2), C7(H7A), C8(H8), C10(H10),
 C20(H20), C27(H27), C26(H26), C30(H30), C29(H29), C28(H28), C14(H14)
7.c Fitted hexagon refined as free rotating group:
 C27(C26,C25,C30,C29,C28)
7.d X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N2(H2A,H2B)
7.e Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
7.f Idealised tetrahedral OH refined as rotating group:
 O13(H13), O9(H9), O3(H3), O11(H11), O6(H6), O7(H7)
;
_shelx_res_checksum              37836
_shelx_hkl_checksum              43318
_olex2_submission_special_instructions 'No special instructions were received'