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_7131674
_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         '2(C6 H3 Cl3), C44 H26 O8'
_chemical_formula_sum            'C56 H32 Cl6 O8'
_chemical_formula_weight         1045.51
_chemical_name_systematic        CP-Py-2-TCB
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-06
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-12 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.898(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   27.5399(14)
_cell_length_b                   11.8206(8)
_cell_length_c                   7.2355(4)
_cell_measurement_reflns_used    4922
_cell_measurement_temperature    113
_cell_measurement_theta_max      31.9510
_cell_measurement_theta_min      3.4540
_cell_volume                     2352.4(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.899
_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    -61.00  72.00   0.25    5.00    --    0.00  45.00  15.00  532
  2  \w    -85.25  44.00   0.25    5.00    --    0.00  45.00 193.00  517
  3  \w     -2.00  43.00   0.25    5.00    --    0.00  45.00 157.00  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      0.0171931000
_diffrn_orient_matrix_UB_12      -0.0310452000
_diffrn_orient_matrix_UB_13      0.0558676000
_diffrn_orient_matrix_UB_21      -0.0174066000
_diffrn_orient_matrix_UB_22      -0.0068175000
_diffrn_orient_matrix_UB_23      0.0681328000
_diffrn_orient_matrix_UB_31      -0.0081591000
_diffrn_orient_matrix_UB_32      -0.0508963000
_diffrn_orient_matrix_UB_33      -0.0432576000
_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  0.0615
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17520
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.675
_diffrn_reflns_theta_min         2.812
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92737
_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    1.476
_exptl_crystal_description       plate
_exptl_crystal_F_000             1068
_exptl_crystal_recrystallization_method
'obtained by desolvation-triggered structural transformation'
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0558P)^2^+3.9835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2596
_reflns_number_total             3735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01877f2.cif
_cod_data_source_block           CP-Py-2-TCB
_cod_depositor_comments
'Adding full bibliography for 7131672--7131678.cif.'
_cod_database_code               7131674
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.929
_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
 C6-C7A \\sim C6-C7B
 with sigma of 0.02
 C6-C11A \\sim C6-C11B
 with sigma of 0.02
 C9-C8A \\sim C9-C8B
 with sigma of 0.02
 C9-C10A \\sim C9-C10B
 with sigma of 0.02
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.02
 C9-C11A \\sim C9-C11B
 with sigma of 0.04
 C6-C10A \\sim C6-C10B
 with sigma of 0.04
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.02
 C6-C8A \\sim C6-C8B
 with sigma of 0.04
 C9-C7A \\sim C9-C7B
 with sigma of 0.04
3. Restrained planarity
 C8B, C7B, C9, C10B, C11B, C6
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C11A \\sim C10A \\sim C9 \\sim C8A \\sim C7A \\sim C6: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C11B \\sim C7B \\sim C8B \\sim C10B: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.08 within 1.7A
C7A \\sim C8A \\sim C11A \\sim C10A: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.08 within 1.7A
Uanis(C7A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C10A, C11A, C6, C8A, C7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7B, C8B, C6, C11B, C10B, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C11B)=Sof(H11A)=Sof(C10B)=Sof(H10A)=Sof(C8B)=Sof(H8A)=Sof(C7B)=Sof(H7A)=1-
 FVAR(1)
 Sof(C11A)=Sof(H11)=Sof(C10A)=Sof(H10)=Sof(C8A)=Sof(H8)=Sof(C7A)=Sof(H7)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C11A(H11), C10A(H10), C8A(H8), C7A(H7), C11B(H11A), C10B(H10A), C8B(H8A),
 C7B(H7A), C1(H1), C2(H2A), C18(H18), C16(H16), C15(H15)
7.b Fitted hexagon refined as free rotating group:
 C6(C11A,C10A,C9,C8A,C7A)
7.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              60294
_shelx_hkl_checksum              99894
_olex2_submission_original_sample_id TBAPy-DCB-TCB-3-1-1h-dry
_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 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.820