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_7131677
_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(C8 H11 N)'
_chemical_formula_sum            'C68 H59 N3 O8'
_chemical_formula_weight         1046.18
_chemical_name_systematic        CP-Py-2-DMAni
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-31
_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                 94.080(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4693(4)
_cell_length_b                   14.233(2)
_cell_length_c                   24.1720(16)
_cell_measurement_reflns_used    6649
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.6360
_cell_measurement_theta_min      1.8820
_cell_volume                     2563.2(4)
_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      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.901
_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   1.00    2.00    --   25.00  45.00   0.00  180
  2  \w    -90.00  90.00   1.00    2.00    --   25.00  45.00  90.00  180
  3  \w    -90.00  90.00   1.00    2.00    --   25.00  45.00 180.00  180
  4  \w    -90.00  90.00   1.00    2.00    --   25.00  45.00 270.00  180
;
_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      -0.0334131000
_diffrn_orient_matrix_UB_12      -0.0043664000
_diffrn_orient_matrix_UB_13      0.0310946000
_diffrn_orient_matrix_UB_21      0.0245647000
_diffrn_orient_matrix_UB_22      -0.0554341000
_diffrn_orient_matrix_UB_23      0.0005372000
_diffrn_orient_matrix_UB_31      0.1007549000
_diffrn_orient_matrix_UB_32      0.0123015000
_diffrn_orient_matrix_UB_33      0.0127845000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.811
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            32342
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        29.117
_diffrn_reflns_theta_max         33.848
_diffrn_reflns_theta_min         1.896
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65956
_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    1.356
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method
'obtained by desolvation-triggered structural transformation'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         6267
_refine_ls_number_restraints     150
_refine_ls_restrained_S_all      1.273
_refine_ls_R_factor_all          0.2104
_refine_ls_R_factor_gt           0.1210
_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          0.3631
_refine_ls_wR_factor_ref         0.4120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2802
_reflns_number_total             6267
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01877f2.cif
_cod_data_source_block           CP-Py-2-DMAni
_cod_depositor_comments
'Adding full bibliography for 7131672--7131678.cif.'
_cod_database_code               7131677
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.986
_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
 N2-C38 = N2-C37 = N1-C30 = N1-C29
 1.46 with sigma of 0.02
 C30-C29
 2.495 with sigma of 0.02
 N2-C31 = N1-C23
 1.396 with sigma of 0.02
 C38-C37
 2.495 with sigma of 0.02
 C31-C38 \\sim C31-C37 \\sim C23-C29 \\sim C23-C30
 with sigma of 0.04
 C28-N1 \\sim C24-N1 \\sim C36-N2 \\sim C32-N2
 with sigma of 0.04
 O1-C15 \\sim O3-C22
 with sigma of 0.02
 O4-C22 \\sim O2-C15
 with sigma of 0.02
3. Restrained planarity
 N1, C23, C28, C27, C26, C25, C24
 with sigma of 0.1
 N1, C29, C30, C23
 with sigma of 0.1
4. Rigid bond restraints
 C29, C24, C25, C23, N1, C26, C28, C30, C27
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C37, N2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
N2 \\sim C38 \\sim C37 \\sim C36 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim
C35: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
1.7A
C38 \\sim N2 \\sim C37: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
C23 \\sim C28 \\sim C27 \\sim C26 \\sim C25 \\sim C24: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C36 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C27 \\sim C26 \\sim C25 \\sim C24 \\sim C28 \\sim C23: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C27 \\sim C26 \\sim C25 \\sim C24 \\sim C23 \\sim C28: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C34 \\sim C33 \\sim C32 \\sim C31 \\sim C36 \\sim C35: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C29 \\sim N1 \\sim C30: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
6. Others
 Fixed Sof: C24(0.5) H24(0.5) C25(0.5) H25(0.5) C26(0.5) H26(0.5) C27(0.5)
 H27(0.5) C28(0.5) H28(0.5) C23(0.5) N1(0.5) C29(0.5) H29A(0.5) H29B(0.5)
 H29C(0.5) C30(0.5) H30A(0.5) H30B(0.5) H30C(0.5)
7.a Me refined with riding coordinates:
 C38(H38A,H38B,H38C), C37(H37A,H37B,H37C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C2(H2A), C10(H10), C14(H14), C17(H17), C11(H11), C21(H21),
 C20(H20), C13(H13), C18(H18), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
7.c Fitted hexagon refined as free rotating group:
 C24(C25,C26,C27,C28,C23), C32(C33,C34,C35,C36,C31)
7.d Tetrahedral OH refined with riding coordinates:
 O2(H2), O4(H4)
;
_shelx_res_checksum              93125
_shelx_hkl_checksum              11583
_olex2_submission_original_sample_id CP-Py-DMA-Form2
_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 1.882
_oxdiff_exptl_absorpt_empirical_full_min 0.675