Statically and dynamically flexible hydrogen-bonded frameworks based on 4,5,9,10-tetrakis(4-carboxyphenyl)pyrene.
Hashimoto, Taito; Oketani, Ryusei; Inoue, Asato; Okubo, Kohei; Oka, Kouki; Tohnai, Norimitsu; Kamiya, Kazuhide; Nakanishi, Shuji; Hisaki, Ichiro; Chemical communications (Cambridge, England) 59 (2023) 7224–7227; doi:10.1039/d3cc01877f

data_7131678
_publ_section_title
;
 Statically and dynamically flexible hydrogen-bonded frameworks based on
 4,5,9,10-tetrakis(4-carboxyphenyl)pyrene.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7224
_journal_page_last               7227
_journal_paper_doi               10.1039/d3cc01877f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C44 H26 O8, 3(C11 H10)'
_chemical_formula_sum            'C77 H56 O8'
_chemical_formula_weight         1109.21
_chemical_name_systematic        4,5,9,10-Tetrakis(4-carboxyphenyl)pyrene
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.763(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6554(13)
_cell_length_b                   15.342(3)
_cell_length_c                   24.524(5)
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    113
_cell_measurement_theta_max      24.8550
_cell_measurement_theta_min      2.6930
_cell_volume                     2870.4(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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      113
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.889
_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    -94.00  86.00   0.25   15.00    --   -4.00  45.00  86.00  720
  2  \w    -72.00  30.00   0.25   15.00    --   -4.00  45.00 122.00  408
  3  \w    -78.00  16.00   0.25   15.00    --   -4.00  45.00  15.00  376
  4  \w    -77.50 -32.50   0.25   15.00    --   -4.00  45.00  51.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0042992000
_diffrn_orient_matrix_UB_12      0.0454670000
_diffrn_orient_matrix_UB_13      -0.0049916000
_diffrn_orient_matrix_UB_21      0.0501548000
_diffrn_orient_matrix_UB_22      -0.0080134000
_diffrn_orient_matrix_UB_23      -0.0225682000
_diffrn_orient_matrix_UB_31      -0.0780847000
_diffrn_orient_matrix_UB_32      -0.0026758000
_diffrn_orient_matrix_UB_33      -0.0175810000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3556
_diffrn_reflns_av_unetI/netI     0.3321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            43799
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.191
_diffrn_reflns_theta_min         2.655
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       plate
_exptl_crystal_F_000             1164
_exptl_crystal_recrystallization_method
'obtained by solvent exchange-triggered structural transformation'
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         7579
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.3606
_refine_ls_R_factor_gt           0.1408
_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^)+(0.1983P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3410
_refine_ls_wR_factor_ref         0.4412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2278
_reflns_number_total             7579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01877f2.cif
_cod_data_source_block           CP-Py-1-MeNaph
_cod_depositor_comments
'Adding full bibliography for 7131672--7131678.cif.'
_cod_original_cell_volume        2870.4(10)
_cod_database_code               7131678
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C34-H34
 0.95 with sigma of 0.005
 C35-H34 \\sim C38-H34
 with sigma of 0.02
3. Restrained planarity
 H34, C34, C35, C38, C37, C36, C39
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C28 \\sim C27 \\sim C26 \\sim C25 \\sim C24 \\sim C29 \\sim C30 \\sim C31 \\sim
C32 \\sim C23: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
5. Others
 Fixed Sof: C39(0.5) H39A(0.5) H39B(0.5) H39C(0.5) H34(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C3(H3), C1(H1), C17(H17), C21(H21), C11(H11), C10(H10), C13(H13),
 C2(H2A), C20(H20), C18(H18), C35(H35), C36(H36), C37(H37), C25(H25), C26(H26),
 C27(H27), C28(H28), C32(H32), C31(H31), C30(H30)
6.b Tetrahedral OH refined with riding coordinates:
 O4(H4), O2(H2)
6.c Naphthalene refined as free rotating group:
 C25(C26,C27,C28,C29,C24,C23,C32,C31,C30)
6.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C39(H39A,H39B,H39C)
;
_shelx_res_checksum              74296
_shelx_hkl_checksum              537
_olex2_submission_original_sample_id CP-Py-2-DCB-dropped-Menaph
_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.831