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_3000559
_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, 1.5(C6 H6 N2 O), 1.168(C2 H3 N)'
_chemical_formula_sum            'C17.34 H18.5 N4.17 O7.5'
_chemical_formula_weight         405.23
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                78.119(2)
_cell_angle_beta                 84.652(2)
_cell_angle_gamma                88.580(2)
_cell_formula_units_Z            4
_cell_length_a                   6.98750(10)
_cell_length_b                   15.1552(3)
_cell_length_c                   19.5219(4)
_cell_measurement_reflns_used    14841
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.1960
_cell_measurement_theta_min      2.1620
_cell_volume                     2014.18(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Dectris Eiger X 1M'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'DECTRIS EIGER X 1M'
_diffrn_measurement_method       'Shutterless \w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0050608000
_diffrn_orient_matrix_UB_12      0.0154623000
_diffrn_orient_matrix_UB_13      -0.0421661000
_diffrn_orient_matrix_UB_21      0.0444486000
_diffrn_orient_matrix_UB_22      0.0486932000
_diffrn_orient_matrix_UB_23      0.0009354000
_diffrn_orient_matrix_UB_31      0.1078044000
_diffrn_orient_matrix_UB_32      -0.0196911000
_diffrn_orient_matrix_UB_33      -0.0065262000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.812
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20365
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        29.157
_diffrn_reflns_theta_max         30.497
_diffrn_reflns_theta_min         1.569
_diffrn_source                   'Synchrotron radiation SPring-8 BL40XU'
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             847
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       0.158(7)
_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   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     676
_refine_ls_number_reflns         8226
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0667
_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^)+(0.1230P)^2^+0.9835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1886
_refine_ls_wR_factor_ref         0.1916
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7481
_reflns_number_total             8226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1TACA1INA-EtACN_fill.cif
_cod_data_source_block           1taca1ina-etacn
_cod_depositor_comments
'Releasing structure 3000559 into public domain as published material.'
_cod_original_formula_sum        'C17.34 H18.50 N4.17 O7.50'
_cod_database_code               3000559
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  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. Uiso/Uaniso restraints and constraints
Uanis(C68) \\sim Ueq, Uanis(N70) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(N64)
\\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C62) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 N70, C69, C68, N64, C63, C62, C65, N67, C66
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O55B)=Sof(H55B)=Sof(O56B)=Sof(C28)=Sof(C29)=Sof(H29)=Sof(C33)=Sof(H33)=
 Sof(N31)=Sof(C34)=Sof(C32)=Sof(H32)=Sof(N36)=Sof(H36A)=Sof(H36B)=Sof(O37)=
 Sof(C30)=Sof(H30)=Sof(O43B)=Sof(O44B)=Sof(H44B)=1-FVAR(1)
 Sof(O44A)=Sof(H44A)=Sof(O43A)=Sof(O27)=Sof(C19)=Sof(N26)=Sof(H26A)=Sof(H26B)=
 Sof(C21)=Sof(H21)=Sof(N22)=Sof(C23)=Sof(H23)=Sof(C20)=Sof(H20)=Sof(C24)=
 Sof(H24)=Sof(C25)=Sof(O56A)=Sof(O55A)=Sof(H55A)=FVAR(1)
 Sof(N67)=Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=Sof(C66)=FVAR(2)
 Sof(C63)=Sof(N64)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=FVAR(3)
 Sof(C69)=Sof(N70)=Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H68C)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B), C39(H39A,H39B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C14(H14), C3(H3), C53(H53), C12(H12), C5(H5), C2(H2),
 C41(H41), C15(H15), C21(H21), C23(H23), C20(H20), C24(H24), C29(H29), C33(H33),
  C32(H32), C30(H30)
5.c X=CH2 refined with riding coordinates:
 N17(H17A,H17B), N8(H8A,H8B), N26(H26A,H26B), N36(H36A,H36B)
5.d Idealised Me refined as rotating group:
 C65(H65A,H65B,H65C), C68(H68A,H68B,H68C), C62(H62A,H62B,H62C)
5.e Idealised tetrahedral OH refined as rotating group:
 O60(H60), O57(H57), O48(H48), O44A(H44A), O45(H45), O55B(H55B), O44B(H44B),
 O55A(H55A)
;
_shelx_res_checksum              49695
_shelx_hkl_checksum              76537
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.793
_oxdiff_exptl_absorpt_empirical_full_min 0.655