A hydrogen-bonded organic framework possessing one-dimensional wide channels surrounded by naphthalenediimide plane
Murata, Yuzuki; Hashimoto, Taito; Oketani, Ryusei; Naruoka, Miki; Paitandi, Rajendra Prasad; Tonai, Norimitsu; Seki, Shu; Hisaki, Ichiro; Chemical Science  (2025) –; doi:10.1039/D5SC07488F

data_1576385
_publ_section_title
;
 A hydrogen-bonded organic framework possessing one-dimensional wide
 channels surrounded by naphthalenediimide plane
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC07488F
_journal_year                    2025
_chemical_formula_moiety         'C54 H30 N2 O12, 6[C6 H3 Cl3]'
_chemical_formula_sum            'C90 H48 Cl18 N2 O12'
_chemical_formula_weight         1919.41
_chemical_name_common            CPNDI-1(TCB)
_chemical_name_systematic
'5',5''''-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydrobenzo[lmn][3,8]phenanthroline-2,7-diyl)bis([1,1':3',1''-terphenyl]-4,4''-dicarboxylic acid)'
_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             2024-11-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-08-05 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                112.684(8)
_cell_angle_beta                 93.637(11)
_cell_angle_gamma                90.887(10)
_cell_formula_units_Z            1
_cell_length_a                   4.9531(8)
_cell_length_b                   19.0154(15)
_cell_length_c                   23.435(2)
_cell_measurement_reflns_used    3097
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.9410
_cell_measurement_theta_min      2.0150
_cell_volume                     2030.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       '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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -90.00  90.00   0.50    2.00    --   25.00  45.00   0.00  360
  2  \w    -90.00  90.00   0.50    3.00    --   25.00  45.00 -90.00  360
  3  \w    -90.00  90.00   0.50    3.00    --   25.00  45.00-180.00  360
  4  \w    -90.00  90.00   0.50    3.00    --   25.00  45.00-270.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0308298000
_diffrn_orient_matrix_UB_12      -0.0449809000
_diffrn_orient_matrix_UB_13      -0.0134962000
_diffrn_orient_matrix_UB_21      -0.0204869000
_diffrn_orient_matrix_UB_22      -0.0015770000
_diffrn_orient_matrix_UB_23      -0.0350561000
_diffrn_orient_matrix_UB_31      0.1598323000
_diffrn_orient_matrix_UB_32      0.0105322000
_diffrn_orient_matrix_UB_33      0.0010118000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.81022
_diffrn_reflns_av_R_equivalents  0.2126
_diffrn_reflns_av_unetI/netI     0.3463
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22250
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        29.087
_diffrn_reflns_theta_max         33.605
_diffrn_reflns_theta_min         2.005
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49603
_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_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMF and 1,2,4-trichlorobenzene'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         9320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.2544
_refine_ls_R_factor_gt           0.1618
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3707
_refine_ls_wR_factor_ref         0.4485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2421
_reflns_number_total             9320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07488f2.cif
_cod_data_source_block           CPNDI-1(TCB)
_cod_original_formula_sum        'C90 H48 N2 O12 Cl18'
_cod_database_code               1576385
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C11(H11), C19(H19), C9(H9), C23(H23), C13(H13), C16(H16), C26(H26),
 C18(H18), C15(H15), C25(H25), C5(H5), C4(H4A)
2.b Tetrahedral OH refined with riding coordinates:
 O6(H6), O4(H4)
;
_shelx_res_checksum              28626
_shelx_fab_checksum              69432
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_original_sample_id 029-NDI-15
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.859
_oxdiff_exptl_absorpt_empirical_full_min 0.249