Construction of Isostructural Hydrogen-bonded Organic Frameworks: Limitations and Possibilities of Pore Expansion
Suzuki, Yuto; GUTIÉRREZ, MARIO; Tanaka, Senri; Gomez Garcia, Eduardo; Tohnai, Norimitsu; Yasuda, Nobuhiro; Matubayasi, Nobuyuki; Douhal, Abderrazzak; Hisaki, Ichiro; Chemical Science  (2021) –; doi:10.1039/D1SC02690A

data_1563671
_publ_section_title
;
 Construction of Isostructural Hydrogen-bonded Organic Frameworks:
 Limitations and Possibilities of Pore Expansion
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02690A
_journal_year                    2021
_chemical_formula_moiety         'C96 H66 O12, 2(C6 H3 Cl3)'
_chemical_formula_sum            'C108 H72 Cl6 O12'
_chemical_formula_weight         1774.35
_chemical_name_common            BPTp
_chemical_name_systematic
'4',4''',4''''',4''''''',4'''''''''-(11-(4'-methyl-[1,1'-biphenyl]-4-yl)triphenylene-2,3,6,7,10-pentayl)pentakis(([1,1'-biphenyl]-4-carboxylic acid))'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-30 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.504(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3082(3)
_cell_length_b                   53.6910(12)
_cell_length_c                   30.7096(6)
_cell_measurement_reflns_used    8497
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      74.0530
_cell_measurement_theta_min      4.8260
_cell_volume                     15216.2(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.953
_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    -17.00  89.00   0.50    2.00    --    0.00  37.00   0.00  212
  2  \w     -8.00  21.00   0.50    2.00    --    0.00  57.00-120.00   58
  3  \w     37.00  62.00   0.50    2.00    --    0.00  57.00-120.00   50
  4  \w      5.00 108.00   0.50   18.00    --   94.90 -61.00  90.00  206
  5  \w     90.00 180.00   0.50   18.00    --   94.90  82.00 120.00  180
  6  \w      6.00 113.00   0.50   18.00    --   94.90 -82.00  90.00  214
  7  \w    151.00 184.00   0.50   18.00    --   94.90  30.00 -30.00   66
  8  \w     71.00 125.00   0.50   18.00    --   94.90 -82.00 -90.00  108
  9  \w     75.00 153.00   0.50   18.00    --   94.90  77.00  30.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0092102000
_diffrn_orient_matrix_UB_12      -0.0022466000
_diffrn_orient_matrix_UB_13      -0.0503249000
_diffrn_orient_matrix_UB_21      -0.0037957000
_diffrn_orient_matrix_UB_22      0.0286064000
_diffrn_orient_matrix_UB_23      -0.0040381000
_diffrn_orient_matrix_UB_31      0.1665330000
_diffrn_orient_matrix_UB_32      0.0005271000
_diffrn_orient_matrix_UB_33      0.0037350000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       65
_diffrn_reflns_limit_k_min       -61
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            37007
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.469
_diffrn_reflns_theta_min         3.337
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.775
_exptl_crystal_description       block
_exptl_crystal_F_000             6023
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: N,N-dimethylformamide, 1,2,4-trichlorobenzene'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.377
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     696
_refine_ls_number_reflns         14857
_refine_ls_number_restraints     826
_refine_ls_restrained_S_all      1.351
_refine_ls_R_factor_all          0.1786
_refine_ls_R_factor_gt           0.1349
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3858
_refine_ls_wR_factor_ref         0.4215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7913
_reflns_number_total             14857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02690a2.cif
_cod_data_source_block           BPTp-1-TCB
_cod_database_code               1563671
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.935
_reflns_odcompleteness_completeness 98.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C44B-C47B
 1.488 with sigma of 0.02
 O6B-C47B
 1.253 with sigma of 0.02
 O5B-C47B
 1.253 with sigma of 0.02
 O5B-O6B
 2.221 with sigma of 0.04
 C44B-O5B
 2.35 with sigma of 0.08
 O6B-C44B
 2.35 with sigma of 0.08
 O1A-C23A \\sim O1B-C23B
 with sigma of 0.02
 C16-C17A \\sim C16-C17B
 with sigma of 0.02
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.02
 C17A-C22A \\sim C17B-C22B
 with sigma of 0.02
 C18A-C19A \\sim C18B-C19B
 with sigma of 0.02
 C19A-C20A \\sim C19B-C20B
 with sigma of 0.02
 C20A-C21A \\sim C20B-C21B
 with sigma of 0.02
 C20A-C23A \\sim C20B-C23B
 with sigma of 0.02
 C21A-C22A \\sim C21B-C22B
 with sigma of 0.02
 O2A-C23A \\sim O2B-C23B
 with sigma of 0.02
 O1A-C20A \\sim O1B-C20B
 with sigma of 0.04
 O1A-O2A \\sim O1B-O2B
 with sigma of 0.04
 C16-C18A \\sim C16-C18B
 with sigma of 0.04
 C16-C22A \\sim C16-C22B
 with sigma of 0.04
 C17A-C19A \\sim C17B-C19B
 with sigma of 0.04
 C17A-C21A \\sim C17B-C21B
 with sigma of 0.04
 C18A-C20A \\sim C18B-C20B
 with sigma of 0.04
 C18A-C22A \\sim C18B-C22B
 with sigma of 0.04
 C19A-C21A \\sim C19B-C21B
 with sigma of 0.04
 C19A-C23A \\sim C19B-C23B
 with sigma of 0.04
 C20A-C22A \\sim C20B-C22B
 with sigma of 0.04
 C20A-O2A \\sim C20B-O2B
 with sigma of 0.04
 C21A-C23A \\sim C21B-C23B
 with sigma of 0.04
 O5B-C47B \\sim O6A-C47A
 with sigma of 0.02
 C40-C41B \\sim C40-C41A
 with sigma of 0.02
 C41B-C46B \\sim C41A-C42A
 with sigma of 0.02
 C41B-C42B \\sim C41A-C46A
 with sigma of 0.02
 C46B-C45B \\sim C42A-C43A
 with sigma of 0.02
 C45B-C44B \\sim C43A-C44A
 with sigma of 0.02
 C44B-C43B \\sim C44A-C45A
 with sigma of 0.02
 C44B-C47B \\sim C44A-C47A
 with sigma of 0.02
 C43B-C42B \\sim C45A-C46A
 with sigma of 0.02
 O6B-C47B \\sim O5A-C47A
 with sigma of 0.02
 O5B-C44B \\sim O6A-C44A
 with sigma of 0.04
 O5B-O6B \\sim O6A-O5A
 with sigma of 0.04
 C40-C46B \\sim C40-C42A
 with sigma of 0.04
 C40-C42B \\sim C40-C46A
 with sigma of 0.04
 C41B-C45B \\sim C41A-C43A
 with sigma of 0.04
 C41B-C43B \\sim C41A-C45A
 with sigma of 0.04
 C46B-C44B \\sim C42A-C44A
 with sigma of 0.04
 C46B-C42B \\sim C42A-C46A
 with sigma of 0.04
 C45B-C43B \\sim C43A-C45A
 with sigma of 0.04
 C45B-C47B \\sim C43A-C47A
 with sigma of 0.04
 C44B-C42B \\sim C44A-C46A
 with sigma of 0.04
 C44B-O6B \\sim C44A-O5A
 with sigma of 0.04
 C43B-C47B \\sim C45A-C47A
 with sigma of 0.04
3. Restrained planarity
 C41B, C42B, C43B, C44B, C45B, C46B, C47B, O5B, O6B
 with sigma of 0.1
4. Rigid bond restraints
 C41B, C46B, C45B, C44B, C43B, C42B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C41A, C46A, C42A, C43A, C45A, C44A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C37, C38, C39, C40, C41, C42
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C17A, C22A, C21A, C20A, C19A, C18A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
6. Others
 Sof(C17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(C21B)=
 Sof(H21B)=Sof(C22B)=Sof(H22B)=Sof(C23B)=Sof(O1B)=Sof(H1B)=Sof(O2B)=Sof(H2B)=1-
 FVAR(1)
 Sof(O1A)=Sof(H1A)=Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(O2A)=Sof(H2A)=Sof(C23A)=FVAR(1)
 Sof(C41A)=Sof(C46A)=Sof(H46A)=Sof(C45A)=Sof(H45A)=Sof(C44A)=Sof(C43A)=
 Sof(H43A)=Sof(C42A)=Sof(H42A)=Sof(C47A)=Sof(O6A)=Sof(H6A)=Sof(O5A)=Sof(H5A)=1-
 FVAR(2)
 Sof(O5B)=Sof(H5B)=Sof(C41B)=Sof(C46B)=Sof(H46B)=Sof(C45B)=Sof(H45B)=Sof(C44B)=
 Sof(C43B)=Sof(H43B)=Sof(C42B)=Sof(H42B)=Sof(O6B)=Sof(H6B)=Sof(C47B)=FVAR(2)
7.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C38(H38), C39(H39), C2(H2), C42(H42), C25(H25), C28(H28),
 C41(H41), C26(H26), C15(H15), C29(H29), C46B(H46B), C45B(H45B), C43B(H43B),
 C42B(H42B), C14(H14), C31(H31), C35(H35), C11(H11), C50(H50), C53(H53),
 C52(H52), C18A(H18A), C19A(H19A), C21A(H21A), C22A(H22A), C12(H12), C34(H34),
 C32(H32), C18B(H18B), C19B(H19B), C21B(H21B), C22B(H22B), C46A(H46A),
 C45A(H45A), C43A(H43A), C42A(H42A)
7.b Fitted hexagon refined as free rotating group:
 C41B(C46B,C45B,C44B,C43B,C42B), C51(C50,C49,C48,C53,C52), C17A(C18A,C19A,C20A,
 C21A,C22A)
7.c Tetrahedral OH refined with riding coordinates:
 O5B(H5B), O1A(H1A), O3(H3), O4(H4), O6B(H6B), O2A(H2A), O1B(H1B), O2B(H2B),
 O6A(H6A), O5A(H5A)
;
_shelx_res_checksum              63975
_shelx_hkl_checksum              28348
_shelx_fab_checksum              69245
_platon_squeeze_void_probe_radius 1.20
_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 2.507
_oxdiff_exptl_absorpt_empirical_full_min 0.640