Tetraptycene derivatives: synthesis, structure and their self-assemblies in solid state
Yang, Bin-Bin; Wu, Si-Yuan; Zhang, Qing-Pu; Ma, Hui; Sun, Yu-Ling; Zhang, Chun; RSC Advances 15 (2025) 8293–8299; doi:10.1039/D5RA00376H

data_7250123
_publ_section_title
;
 Tetraptycene derivatives: synthesis, structure and their self-assemblies
 in solid state
;
_journal_issue                   11
_journal_name_full               'RSC Advances'
_journal_page_first              8293
_journal_page_last               8299
_journal_paper_doi               10.1039/D5RA00376H
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         '0.4(C28 H20 O)'
_chemical_formula_sum            'C11.2 H8 O0.4'
_chemical_formula_weight         148.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-08-10 deposited with the CCDC.	2025-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.077(3)
_cell_angle_gamma                90
_cell_formula_units_Z            10
_cell_length_a                   23.7924(9)
_cell_length_b                   8.0783(2)
_cell_length_c                   11.8488(3)
_cell_measurement_reflns_used    7411
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9500
_cell_measurement_theta_min      3.7900
_cell_volume                     2260.01(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_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      2.00  29.00   0.50    0.50    --    0.00 -77.00 120.00   54
  2  \w    -28.00  31.00   0.50    0.50    --    0.00 -82.00  30.00  118
  3  \w    -32.00  24.00   0.50    0.50    --    0.00 -82.00 -90.00  112
  4  \w    -46.00   2.00   0.50    0.50    --    0.00 -77.00 -30.00   96
  5  \w    -10.00  26.00   0.50    0.50    --    0.00 -82.00-180.00   72
  6  \w    -32.00  13.00   0.50    0.50    --    0.00 -82.00  90.00   90
  7  \w      8.00  34.00   0.50    2.00    --   95.20 -82.00  30.00   52
  8  \w      7.00  34.00   0.50    2.00    --   95.20 -82.00  90.00   54
  9  \w      7.00 106.00   0.50    2.00    --   95.20 -61.00  90.00  198
 10  \w     50.00 126.00   0.50    2.00    --   95.20 -82.00 -60.00  152
 11  \w     62.00 114.00   0.50    2.00    --   95.20 -45.00  30.00  104
 12  \w     39.00 115.00   0.50    2.00    --   95.20 -82.00  90.00  152
 13  \w     24.00  95.00   0.50    2.00    --   95.20 -61.00-150.00  142
 14  \w     73.00 177.00   0.50    2.00    --   95.20  15.00  30.00  208
 15  \w    128.00 184.00   0.50    2.00    --   95.20  45.00  90.00  112
 16  \w     46.00 105.00   0.50    2.00    --   95.20 -61.00 -60.00  118
 17  \w     10.00  35.00   0.50    2.00    --   95.20 -61.00 -60.00   50
 18  \w    151.00 177.00   0.50    2.00    --   95.20  15.00 120.00   52
 19  \w     92.00 128.00   0.50    2.00    --   95.20  15.00 120.00   72
 20  \w      8.00  40.00   0.50    2.00    --   95.20 -82.00 -60.00   64
 21  \w     26.00 122.00   0.50    2.00    --   95.20 -82.00-150.00  192
 22  \w      7.00  45.00   0.50    2.00    --   95.20 -45.00  30.00   76
 23  \w     76.00 115.00   0.50    2.00    --   95.20  45.00  90.00   78
 24  \w     81.00 106.00   0.50    2.00    --   95.20 -82.00   0.00   50
 25  \w     99.00 126.00   0.50    2.00    --   95.20 -82.00-180.00   54
 26  \w     92.00 119.00   0.50    2.00    --   95.20 -15.00 120.00   54
 27  \w     79.00 104.00   0.50    2.00    --   95.20 -82.00 120.00   50
 28  \w     11.00  79.00   0.50    2.00    --   95.20 -15.00 120.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0631286000
_diffrn_orient_matrix_UB_12      0.0358917000
_diffrn_orient_matrix_UB_13      -0.0067089000
_diffrn_orient_matrix_UB_21      0.0113563000
_diffrn_orient_matrix_UB_22      -0.1868962000
_diffrn_orient_matrix_UB_23      -0.0096704000
_diffrn_orient_matrix_UB_31      -0.0121552000
_diffrn_orient_matrix_UB_32      0.0120382000
_diffrn_orient_matrix_UB_33      -0.1304265000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22343
_diffrn_reflns_point_group_measured_fraction_full 0.757
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.290
_diffrn_reflns_theta_min         3.744
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6684
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.1021
_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          0.2610
_refine_ls_wR_factor_ref         0.2746
_reflns_Friedel_coverage         0.489
_reflns_Friedel_fraction_full    0.516
_reflns_Friedel_fraction_max     0.477
_reflns_number_gt                5352
_reflns_number_total             6684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra00376h2.cif
_cod_data_source_block           20220711_1
_cod_original_cell_volume        2260.02(12)
_cod_original_formula_sum        'C11.20 H8 O0.40'
_cod_database_code               7250123
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.844
_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. Others
 Fixed X: C23A(0.3845)
3.a Ternary CH refined with riding coordinates:
 C5(H5), C12(H12), C19(H19), C26(H26), C4A(H4A), C11A(H11A), C18A(H18A),
 C25A(H25A)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C2A(H2A),
  C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C13A(H13A), C14A(H14A), C15A(H15A),
 C16A(H16A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C27A(H27A),
 C28A(H28A)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 155 electrons were 
found in a volume of 482\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.4[C4H4O] per Asymmetric Unit 
which account for 144 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              43591
_shelx_hkl_checksum              16098
_shelx_fab_checksum              10880
_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 2.071
_oxdiff_exptl_absorpt_empirical_full_min 0.510