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_7131675
_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'
_chemical_formula_sum            'C44 H26 O8'
_chemical_formula_weight         682.65
_chemical_name_systematic
'4,5,9,10-Tetrakis(4-carboxyphenyl)pyrene N,N-dimethylaniline solvate'
_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             2023-04-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-11 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.013(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   23.4820(13)
_cell_length_b                   17.2143(10)
_cell_length_c                   7.5294(3)
_cell_measurement_reflns_used    4261
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      32.4390
_cell_measurement_theta_min      1.9730
_cell_volume                     3036.1(3)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.903
_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      0.0343908000
_diffrn_orient_matrix_UB_12      -0.0041976000
_diffrn_orient_matrix_UB_13      -0.0010020000
_diffrn_orient_matrix_UB_21      0.0028466000
_diffrn_orient_matrix_UB_22      0.0467986000
_diffrn_orient_matrix_UB_23      -0.0078425000
_diffrn_orient_matrix_UB_31      0.0029285000
_diffrn_orient_matrix_UB_32      0.0033757000
_diffrn_orient_matrix_UB_33      0.1077327000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.811
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18358
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        29.117
_diffrn_reflns_theta_max         33.335
_diffrn_reflns_theta_min         1.675
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40364
_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    0.747
_exptl_crystal_description       plate
_exptl_crystal_F_000             708
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMF, N,N-dimethylaniline'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3692
_refine_ls_number_restraints     125
_refine_ls_restrained_S_all      1.235
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0911
_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          0.3094
_refine_ls_wR_factor_ref         0.3208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2641
_reflns_number_total             3692
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01877f2.cif
_cod_data_source_block           CP-Py-DMAni-1
_cod_depositor_comments
'Adding full bibliography for 7131672--7131678.cif.'
_cod_database_code               7131675
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.998
_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 O(H) groups
2. Restrained distances
 O2A-C12A \\sim O2B-C12B
 with sigma of 0.02
 C4-C6A \\sim C4-C6B
 with sigma of 0.02
 C6A-C7A \\sim C6B-C7B
 with sigma of 0.02
 C6A-C11A \\sim C6B-C11B
 with sigma of 0.02
 O1A-C12A \\sim O1B-C12B
 with sigma of 0.02
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.02
 C9A-C8A \\sim C9B-C8B
 with sigma of 0.02
 C9A-C12A \\sim C9B-C12B
 with sigma of 0.02
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.02
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.02
 O2A-O1A \\sim O2B-O1B
 with sigma of 0.04
 O2A-C9A \\sim O2B-C9B
 with sigma of 0.04
 C4-C7A \\sim C4-C7B
 with sigma of 0.04
 C4-C11A \\sim C4-C11B
 with sigma of 0.04
 C6A-C8A \\sim C6B-C8B
 with sigma of 0.04
 C6A-C10A \\sim C6B-C10B
 with sigma of 0.04
 O1A-C9A \\sim O1B-C9B
 with sigma of 0.04
 C7A-C9A \\sim C7B-C9B
 with sigma of 0.04
 C7A-C11A \\sim C7B-C11B
 with sigma of 0.04
 C9A-C11A \\sim C9B-C11B
 with sigma of 0.04
 C8A-C12A \\sim C8B-C12B
 with sigma of 0.04
 C8A-C10A \\sim C8B-C10B
 with sigma of 0.04
 C12A-C10A \\sim C12B-C10B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C7B \\sim C8B \\sim C9B \\sim C10B \\sim C11B \\sim C6B: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
C10A \\sim C9A \\sim C8A \\sim C7A \\sim C6A \\sim C11A: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
O2B \\sim C12B \\sim O1B: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 1.7A
O1A \\sim C12A \\sim O2A: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 1.7A
Uanis(O1B) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
4. Others
 Sof(O2B)=Sof(H2B)=Sof(O1B)=Sof(C12B)=Sof(C10B)=Sof(H10B)=Sof(C9B)=Sof(C8B)=
 Sof(H8B)=Sof(C7B)=Sof(H7B)=Sof(C6B)=Sof(C11B)=Sof(H11B)=1-FVAR(1)
 Sof(O2A)=Sof(H2A)=Sof(C6A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=
 Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=Sof(O1A)=Sof(C12A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C11A(H11A), C10A(H10A), C8A(H8A), C7A(H7A), C10B(H10B),
 C8B(H8B), C7B(H7B), C11B(H11B)
5.b Fitted hexagon refined as free rotating group:
 C6A(C11A,C10A,C9A,C8A,C7A), C10B(C9B,C8B,C7B,C6B,C11B)
5.c Tetrahedral OH refined with riding coordinates:
 O2A(H2A), O2B(H2B)
;
_shelx_res_checksum              69099
_shelx_hkl_checksum              91666
_shelx_fab_checksum              47717
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.160
_oxdiff_exptl_absorpt_empirical_full_min 0.588