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_7250125
_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         'C30 H24 O2'
_chemical_formula_sum            'C30 H24 O2'
_chemical_formula_weight         416.49
_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             2022-07-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-08-10 deposited with the CCDC.	2025-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.648(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.5743(3)
_cell_length_b                   8.02250(10)
_cell_length_c                   11.7565(2)
_cell_measurement_reflns_used    25809
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8130
_cell_measurement_theta_min      3.9680
_cell_volume                     2085.28(5)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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 1.000
_diffrn_measured_fraction_theta_max 0.990
_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    -32.00  30.00   0.50    0.50    --    0.00 -82.00-180.00  124
  2  \w      5.00  46.00   0.50    0.50    --   32.00  72.00 171.49   82
  3  \w     82.00 120.00   0.50    0.50    --   32.00  72.00 171.49   76
  4  \w    -44.00  55.00   0.50    0.50    --   36.00 -50.00 -95.85  198
  5  \w     22.00  58.00   0.50    0.50    --   48.00  72.00 128.33   72
  6  \w     24.00  82.00   0.50    0.50    --   48.00  72.00-113.28  116
  7  \w     62.00  89.00   0.50    0.50    --   48.00  72.00 128.33   54
  8  \w    100.00 126.00   0.50    0.50    --   48.00  72.00-113.28   52
  9  \w     25.00  55.00   0.50    0.50    --   52.00  72.00-175.98   60
 10  \w     25.00  57.00   0.50    0.50    --   52.00  72.00 -63.40   64
 11  \w     32.00  87.00   0.50    0.50    --   56.00  75.00   5.17  110
 12  \w     34.00  67.00   0.50    0.50    --   60.00  73.00 -38.81   66
 13  \w     36.00  74.00   0.50    0.50    --   64.00  75.00  38.52   76
 14  \w     40.00  80.00   0.50    0.50    --   68.00  75.00  54.76   80
 15  \w    131.00 157.00   0.50    0.50    --   72.00  75.00 -87.01   52
 16  \w     46.00  72.00   0.50    0.50    --   72.00  73.00-120.27   52
 17  \w    117.00 158.00   0.50    0.50    --   72.00  74.00 150.78   82
 18  \w     46.00  72.00   0.50    0.50    --   72.00  73.00  88.09   52
 19  \w     44.00  93.00   0.50    0.50    --   72.00  75.00 -87.01   98
 20  \w     44.00  81.00   0.50    0.50    --   72.00  74.00 -26.11   74
 21  \w     44.00  91.00   0.50    0.50    --   72.00  74.00 150.78   94
 22  \w     48.00  97.00   0.50    0.50    --   76.00  75.00 110.49   98
 23  \w     48.00  85.00   0.50    0.50    --   76.00  75.00-168.62   74
 24  \w     48.00  80.00   0.50    0.50    --   76.00  74.00 -68.99   64
 25  \w    129.00 155.00   0.50    0.50    --   76.00  75.00-168.62   52
 26  \w     99.00 128.00   0.50    0.50    --   80.00  74.00  85.74   58
 27  \w     52.00  94.00   0.50    0.50    --   80.00  74.00  85.74   84
 28  \w     86.00 160.00   0.50    0.50    --   80.00  75.00 166.16  148
 29  \w     52.00  82.00   0.50    0.50    --   80.00  75.00 166.16   60
 30  \w    116.00 170.00   0.50    0.50    --   84.00  60.00  21.18  108
 31  \w     61.00 109.00   0.50    0.50    --   84.00  60.00  21.18   96
 32  \w     59.00  87.00   0.50    0.50    --   84.00  73.00-163.35   56
 33  \w     56.00  92.00   0.50    0.50    --   84.00  74.00 -34.30   72
 34  \w    100.00 137.00   0.50    0.50    --   84.00  67.00 -55.32   74
 35  \w     63.00  96.00   0.50    0.50    --   84.00  67.00 -55.32   66
 36  \w    114.00 173.00   0.50    0.50    --   84.00  73.00-163.35  118
 37  \w     58.00 126.00   0.50    0.50    --   95.20 -82.00  30.00  136
 38  \w      7.00  33.00   0.50    0.50    --   95.20 -82.00  30.00   52
 39  \w     71.00 162.00   0.50    0.50    --   95.20  63.00 -11.94  182
 40  \w     47.00 126.00   0.50    0.50    --   95.20 -82.00 -60.00  158
 41  \w     73.00 185.00   0.50    0.50    --   95.20  57.00 -73.12  224
 42  \w     74.00 183.00   0.50    0.50    --   95.20  67.00  98.74  218
 43  \w     22.00 115.00   0.50    0.50    --   95.20 -61.00-180.00  186
 44  \w     74.00 130.00   0.50    0.50    --   95.20  61.00-133.44  112
 45  \w    126.00 152.00   0.50    0.50    --   95.20  50.00 155.70   52
 46  \w     75.00 110.00   0.50    0.50    --   95.20  50.00 155.70   70
 47  \w     81.00 185.00   0.50    0.50    --   95.20  15.00  60.00  208
 48  \w      6.00 116.00   0.50    0.50    --   95.20 -61.00 -60.00  220
 49  \w    121.00 185.00   0.50    0.50    --   95.20  82.00-120.00  128
 50  \w     89.00 115.00   0.50    0.50    --   95.20  82.00-120.00   52
 51  \w    160.00 185.00   0.50    0.50    --   95.20  62.00 156.98   50
 52  \w     76.00 127.00   0.50    0.50    --   95.20  62.00 156.98  102
 53  \w      8.00 114.00   0.50    0.50    --   95.20 -82.00  90.00  212
 54  \w      7.00 110.00   0.50    0.50    --   95.20 -82.00-180.00  206
 55  \w     68.00 145.00   0.50    0.50    --   95.20  73.00  39.22  154
 56  \w    139.00 164.00   0.50    0.50    --   96.00  75.00-135.45   50
 57  \w     68.00  94.00   0.50    0.50    --   96.00  75.00-135.45   52
;
_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      -0.0650707000
_diffrn_orient_matrix_UB_12      -0.0638693000
_diffrn_orient_matrix_UB_13      -0.0425026000
_diffrn_orient_matrix_UB_21      0.0206822000
_diffrn_orient_matrix_UB_22      -0.0987335000
_diffrn_orient_matrix_UB_23      -0.0974163000
_diffrn_orient_matrix_UB_31      0.0139120000
_diffrn_orient_matrix_UB_32      -0.1517158000
_diffrn_orient_matrix_UB_33      0.0813326000
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            48372
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.441
_diffrn_reflns_theta_min         1.998
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82067
_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    1.327
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.237
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0682
_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^)+(0.0555P)^2^+6.5326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2089
_refine_ls_wR_factor_ref         0.2101
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4028
_reflns_number_total             4205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra00376h2.cif
_cod_data_source_block           20220713_1
_cod_database_code               7250125
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.785
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9770(8)
 0.0230(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C00H(H00H), C00K(H00K), C00L(H00L), C00N(H00N)
3.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C006(H006), C007(H007), C00A(H00A), C00D(H00D), C00J(H00J),
 C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00U(H00U), C00V(H00V)
3.c Idealised Me refined as rotating group:
 C00S(H00B,H00C,H00E), C00W(H00F,H00G,H00I)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              90074
_shelx_hkl_checksum              13708
_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 1.658
_oxdiff_exptl_absorpt_empirical_full_min 0.672