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_7250126
_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         '2(C14 H10 O2), 3(H2 O), C3 H6 O'
_chemical_formula_sum            'C31 H32 O8'
_chemical_formula_weight         532.56
_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   mixed
_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                 91.5810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.1553(2)
_cell_length_b                   11.01180(10)
_cell_length_c                   8.96460(10)
_cell_measurement_reflns_used    42488
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9130
_cell_measurement_theta_min      4.0080
_cell_volume                     2580.97(4)
_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 0.999
_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    -26.00  29.00   0.50    0.50    --    0.00 -82.00  30.00  110
  2  \w      5.00  54.00   0.50    0.50    --   32.00  72.00 -70.54   98
  3  \w    -53.00  54.00   0.50    0.50    --   36.00 -46.00-167.84  214
  4  \w     87.00 121.00   0.50    0.50    --   40.00  72.00  64.68   68
  5  \w     14.00  49.00   0.50    0.50    --   40.00  72.00  64.68   70
  6  \w     25.00  58.00   0.50    0.50    --   52.00  72.00 148.14   66
  7  \w     31.00  63.00   0.50    0.50    --   56.00  74.00  84.13   64
  8  \w     29.00 114.00   0.50    0.50    --   56.00  71.00 -56.63  170
  9  \w     32.00  66.00   0.50    0.50    --   60.00  75.00  46.84   68
 10  \w     33.00  77.00   0.50    0.50    --   60.00  74.00-111.74   88
 11  \w     33.00 102.00   0.50    0.50    --   60.00  75.00-156.15  138
 12  \w    101.00 148.00   0.50    0.50    --   60.00  74.00-111.74   94
 13  \w     36.00  61.00   0.50    0.50    --   64.00  75.00 -25.65   50
 14  \w     41.00  66.00   0.50    0.50    --   68.00  71.00  88.71   50
 15  \w     40.00  68.00   0.50    0.50    --   68.00  75.00   3.32   56
 16  \w     45.00  74.00   0.50    0.50    --   72.00  73.00 -17.12   58
 17  \w     44.00  76.00   0.50    0.50    --   72.00  75.00 150.53   64
 18  \w    102.00 161.00   0.50    0.50    --   72.00  74.00 119.22  118
 19  \w     44.00  92.00   0.50    0.50    --   72.00  74.00 119.22   96
 20  \w    132.00 165.00   0.50    0.50    --   76.00  75.00 168.56   66
 21  \w     48.00  79.00   0.50    0.50    --   76.00  75.00 168.56   62
 22  \w     48.00  79.00   0.50    0.50    --   76.00  75.00 -50.29   62
 23  \w     48.00  78.00   0.50    0.50    --   76.00  74.00 -71.56   60
 24  \w     55.00 100.00   0.50    0.50    --   80.00  68.00 -83.21   90
 25  \w    134.00 167.00   0.50    0.50    --   80.00  68.00 -83.21   66
 26  \w     56.00  84.00   0.50    0.50    --   84.00  75.00  19.16   56
 27  \w     95.00 173.00   0.50    0.50    --   84.00  70.00-128.67  156
 28  \w     58.00  89.00   0.50    0.50    --   84.00  70.00-128.67   62
 29  \w     69.00 126.00   0.50    0.50    --   95.20  71.00  91.45  114
 30  \w     86.00 127.00   0.50    0.50    --   95.20 -82.00-150.00   82
 31  \w     96.00 127.00   0.50    0.50    --   95.20 -82.00-120.00   62
 32  \w     43.00  70.00   0.50    0.50    --   95.20 -82.00-150.00   54
 33  \w     56.00 105.00   0.50    0.50    --   95.20 -82.00   0.00   98
 34  \w     57.00 102.00   0.50    0.50    --   95.20 -82.00  30.00   90
 35  \w     73.00 182.00   0.50    0.50    --   95.20  60.00-170.43  218
 36  \w     71.00 185.00   0.50    0.50    --   95.20  65.00 132.00  228
 37  \w    120.00 185.00   0.50    0.50    --   95.20  63.00 -36.02  130
 38  \w     73.00 182.00   0.50    0.50    --   95.20  61.00   7.80  218
 39  \w    144.00 184.00   0.50    0.50    --   95.20  61.00  60.00   80
 40  \w     84.00 125.00   0.50    0.50    --   95.20 -82.00  60.00   82
 41  \w     70.00 181.00   0.50    0.50    --   95.20  66.00  81.38  222
 42  \w     71.00 116.00   0.50    0.50    --   95.20  63.00 -36.02   90
 43  \w     49.00  77.00   0.50    0.50    --   95.20 -82.00  60.00   56
 44  \w     72.00 110.00   0.50    0.50    --   95.20  61.00  60.00   76
 45  \w     74.00 183.00   0.50    0.50    --   95.20  54.00 -56.52  218
 46  \w     72.00 185.00   0.50    0.50    --   95.20  64.00-117.12  226
 47  \w     67.00 181.00   0.50    0.50    --   95.20  75.00  26.51  228
 48  \w     72.00 127.00   0.50    0.50    --   95.20  61.00   0.00  110
 49  \w    156.00 185.00   0.50    0.50    --   95.20  57.00 165.10   58
 50  \w     72.00 115.00   0.50    0.50    --   95.20  61.00-150.00   86
 51  \w     42.00 127.00   0.50    0.50    --   95.20 -82.00-180.00  170
 52  \w     21.00  47.00   0.50    0.50    --   95.20 -82.00   0.00   52
 53  \w     75.00 122.00   0.50    0.50    --   95.20  57.00 165.10   94
 54  \w     57.00  83.00   0.50    0.50    --   95.20 -82.00-120.00   52
 55  \w     10.00 110.00   0.50    0.50    --   95.20 -61.00  60.00  200
 56  \w    154.00 180.00   0.50    0.50    --   95.20  71.00  91.45   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      -0.0512340000
_diffrn_orient_matrix_UB_12      0.0665403000
_diffrn_orient_matrix_UB_13      -0.0270750000
_diffrn_orient_matrix_UB_21      0.0285965000
_diffrn_orient_matrix_UB_22      0.1220014000
_diffrn_orient_matrix_UB_23      -0.0074096000
_diffrn_orient_matrix_UB_31      0.0052856000
_diffrn_orient_matrix_UB_32      -0.0159646000
_diffrn_orient_matrix_UB_33      -0.1696633000
_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  0.0649
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            59598
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.157
_diffrn_reflns_theta_min         3.381
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29028
_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    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0624P)^2^+1.4178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4967
_reflns_number_total             5207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra00376h2.cif
_cod_data_source_block           20220715_1
_cod_database_code               7250126
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.687
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H,H) groups
2.a Free rotating group:
 O002(H00A,H00B), O004(H00D,H00E), O008(H00F,H00I)
2.b Ternary CH refined with riding coordinates:
 C00S(H00S), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00G(H00G), C00H(H00H), C00J(H00J), C00M(H00M), C00N(H00N),
 C00O(H00O), C00R(H00R), C00U(H00U), C00V(H00V), C00W(H00W), C010(H010)
2.d Idealised Me refined as rotating group:
 C011(H01A,H01B,H01C), C013(H01D,H01E,H01F)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003), O005(H005), O006(H006)
;
_shelx_res_checksum              25317
_shelx_hkl_checksum              62042
_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 3.369
_oxdiff_exptl_absorpt_empirical_full_min 0.339