Triptycene-like naphthopleiadene as a readily accessible scaffold for supramolecular and materials chemistry.
Amin, Md Khairul; Ye, Chunchun; Pang, Shuhua; Liu, Yuancheng; Taylor, Dominic; Nichol, Gary S.; McKeown, Neil B.; Chemical science 15 (2024) 14968–14976; doi:10.1039/d4sc02755h

data_1572402
_publ_section_title
;
 Triptycene-like naphthopleiadene as a readily accessible scaffold for
 supramolecular and materials chemistry.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              14968
_journal_page_last               14976
_journal_paper_doi               10.1039/d4sc02755h
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H26 O4'
_chemical_formula_sum            'C32 H26 O4'
_chemical_formula_weight         474.561
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_Int_Tables_number      43
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-09
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.02 svn.rb8f36f48 for OlexSys, GUI svn.r6436)
;
_audit_update_record
;
2023-08-04 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.9566(5)
_cell_length_b                   17.6585(2)
_cell_length_c                   8.2176(1)
_cell_measurement_reflns_used    10706
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      75.5570
_cell_measurement_theta_min      5.6990
_cell_volume                     4492.13(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_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    -67.00  27.00   1.00    2.50    --  -41.67  89.00 -96.00   94
  2  \w     -9.00  71.00   1.00    2.50    --   41.67 -89.00 148.00   80
  3  \w     38.00  64.00   1.00    5.00    --  111.00 -89.00 148.00   26
  4  \w    116.00 141.00   1.00    5.00    --  111.00  89.00 -96.00   25
  5  \w   -112.00 -15.00   1.00    2.50    --  -41.67 -57.00-180.00   97
  6  \w    -94.00  -8.00   1.00    2.50    --  -41.67 -19.00 -30.00   86
  7  \w   -113.00 -19.00   1.00    2.50    --  -41.67 -38.00 -90.00   94
  8  \w     61.00 127.00   1.00    2.50    --   41.67 178.00 150.00   66
  9  \w      9.00  34.00   1.00    2.50    --   41.67  82.00 -88.34   25
 10  \w     16.00  42.00   1.00    2.50    --   41.67  57.00  30.00   26
 11  \w     59.00  92.00   1.00    2.50    --   41.67  57.00  30.00   33
 12  \w     14.00  39.00   1.00    2.50    --   46.00  81.00  39.32   25
 13  \w     13.00  41.00   1.00    2.50    --   46.00  82.00 144.14   28
 14  \w     15.00  40.00   1.00    2.50    --   46.00  81.00 -20.07   25
 15  \w     14.00  39.00   1.00    2.50    --   46.00  79.00 117.19   25
 16  \w     14.00  39.00   1.00    2.50    --   46.00  81.00-145.21   25
 17  \w     26.00  53.00   1.00    2.50    --   54.00  70.00 -87.26   27
 18  \w     33.00  58.00   1.00    2.50    --   62.00  70.00 -59.04   25
 19  \w     33.00  58.00   1.00    2.50    --   62.00  71.00   5.95   25
 20  \w     32.00  58.00   1.00    2.50    --   62.00  71.00-133.79   26
 21  \w     33.00  65.00   1.00    2.50    --   62.00  69.00 145.54   32
 22  \w     36.00  63.00   1.00    2.50    --   66.00  71.00  64.01   27
 23  \w     36.00  62.00   1.00    2.50    --   66.00  71.00-163.66   26
 24  \w    109.00 135.00   1.00    2.50    --   66.00  59.00 121.39   26
 25  \w     40.00  65.00   1.00    2.50    --   66.00  59.00 121.39   25
 26  \w    110.00 136.00   1.00    2.50    --   66.00  71.00-163.66   26
 27  \w     36.00  62.00   1.00    2.50    --   66.00  70.00 -28.87   26
 28  \w     40.00  66.00   1.00    2.50    --   70.00  71.00  17.26   26
 29  \w     40.00  66.00   1.00    2.50    --   70.00  71.00 115.39   26
 30  \w    117.00 142.00   1.00    2.50    --   70.00  71.00 115.39   25
 31  \w     46.00  73.00   1.00    2.50    --   74.00  62.00   8.32   27
 32  \w     45.00  72.00   1.00    2.50    --   74.00  70.00-118.86   27
 33  \w     89.00 115.00   1.00    2.50    --   74.00  70.00-118.86   26
 34  \w     44.00  71.00   1.00    2.50    --   74.00  71.00 -37.67   27
 35  \w     44.00  71.00   1.00    2.50    --   74.00  70.00 -88.95   27
 36  \w     48.00  75.00   1.00    5.00    --   78.00  71.00  26.29   27
 37  \w     49.00  76.00   1.00    5.00    --   78.00  69.00-144.42   27
 38  \w     54.00  86.00   1.00    5.00    --   82.00  68.00 127.21   32
 39  \w     54.00  81.00   1.00    5.00    --   82.00  69.00  63.39   27
 40  \w     55.00  82.00   1.00    5.00    --   82.00  63.00 170.50   27
 41  \w     55.00  82.00   1.00    5.00    --   82.00  58.00 -75.98   27
 42  \w     56.00  89.00   1.00    5.00    --   86.00  71.00-171.23   33
 43  \w    125.00 157.00   1.00    5.00    --   86.00  71.00 169.10   32
 44  \w     56.00  82.00   1.00    5.00    --   86.00  71.00 169.10   26
 45  \w     58.00  85.00   1.00    5.00    --   86.00  62.00 -62.59   27
 46  \w     61.00  87.00   1.00    5.00    --   90.00  67.00  36.29   26
 47  \w     65.00  92.00   1.00    5.00    --   90.00  65.00 130.60   27
 48  \w     62.00  88.00   1.00    5.00    --   90.00  65.00  92.31   26
 49  \w     68.00  95.00   1.00    5.00    --   94.00  57.00 -34.69   27
 50  \w     65.00  91.00   1.00    5.00    --   94.00  67.00 -18.80   26
 51  \w    101.00 163.00   1.00    5.00    --   94.00  60.00 151.26   62
 52  \w     67.00  93.00   1.00    5.00    --   94.00  60.00 151.26   26
 53  \w     70.00  96.00   1.00    5.00    --   98.00  61.00   5.68   26
 54  \w     72.00  99.00   1.00    5.00    --  102.00  70.00 172.37   27
 55  \w     73.00 100.00   1.00    5.00    --  102.00  69.00  48.62   27
 56  \w     78.00 104.00   1.00    5.00    --  106.00  64.00 102.76   26
 57  \w    128.00 155.00   1.00    5.00    --  106.00  64.00 102.76   27
 58  \w     81.00 150.00   1.00    5.00    --  110.00  68.00-115.37   69
 59  \w     85.00 114.00   1.00    5.00    --  111.00  61.00-180.00   29
 60  \w     85.00 169.00   1.00    5.00    --  111.00  56.00-128.32   84
 61  \w    124.00 176.00   1.00    5.00    --  111.00  69.00   6.26   52
 62  \w     92.00 133.00   1.00    5.00    --  111.00 -45.00-180.00   41
 63  \w     54.00  79.00   1.00    5.00    --  111.00 -45.00-180.00   25
 64  \w     83.00 147.00   1.00    5.00    --  111.00  61.00 -90.00   64
 65  \w    138.00 168.00   1.00    5.00    --  111.00  61.00-120.00   30
 66  \w     76.00 111.00   1.00    5.00    --  111.00-125.00  90.00   35
 67  \w    122.00 178.00   1.00    5.00    --  111.00  61.00  90.00   56
 68  \w     83.00 119.00   1.00    5.00    --  111.00  69.00   6.26   36
 69  \w     83.00 118.00   1.00    5.00    --  111.00  61.00 150.00   35
 70  \w     83.00 114.00   1.00    5.00    --  111.00  61.00-120.00   31
 71  \w     83.00 120.00   1.00    5.00    --  111.00  61.00  90.00   37
 72  \w     59.00 123.00   1.00    5.00    --  111.00-138.00  57.72   64
 73  \w    120.00 174.00   1.00    5.00    --  111.00  61.00  37.33   54
 74  \w     91.00 176.00   1.00    5.00    --  111.00  45.00-150.00   85
 75  \w     69.00 108.00   1.00    5.00    --  111.00-105.00  75.73   39
 76  \w     83.00 113.00   1.00    5.00    --  111.00  61.00  37.33   30
 77  \w     38.00 105.00   1.00    5.00    --  111.00 -94.00 -60.00   67
 78  \w     85.00 134.00   1.00    5.00    --  111.00 -30.00   0.00   49
 79  \w     56.00  82.00   1.00    5.00    --  111.00 -30.00   0.00   26
 80  \w     84.00 168.00   1.00    5.00    --  111.00  61.00  60.00   84
 81  \w     49.00  99.00   1.00    5.00    --  111.00 -94.00   0.00   50
 82  \w    123.00 149.00   1.00    5.00    --  111.00  61.00-150.00   26
 83  \w     83.00 109.00   1.00    5.00    --  111.00  61.00-150.00   26
 84  \w     72.00 112.00   1.00    5.00    --  111.00-125.00 150.00   40
 85  \w     38.00  98.00   1.00    5.00    --  111.00 -77.00-150.00   60
 86  \w    120.00 169.00   1.00    5.00    --  111.00  63.00  -5.42   49
 87  \w     44.00  70.00   1.00    5.00    --  111.00-125.00 150.00   26
 88  \w     83.00 128.00   1.00    5.00    --  111.00  61.00 -60.75   45
 89  \w     87.00 142.00   1.00    5.00    --  111.00  44.00 -21.04   55
 90  \w     83.00 117.00   1.00    5.00    --  111.00  63.00  -5.42   34
 91  \w    153.00 178.00   1.00    5.00    --  111.00  44.00 -21.04   25
 92  \w    100.00 176.00   1.00    5.00    --  111.00 125.00 -90.00   76
 93  \w    134.00 178.00   1.00    5.00    --  111.00  61.00 120.00   44
 94  \w    129.00 154.00   1.00    5.00    --  111.00  45.00 -60.00   25
 95  \w     92.00 119.00   1.00    5.00    --  111.00  45.00 -60.00   27
 96  \w     40.00  65.00   1.00    5.00    --  111.00 -77.00  30.00   25
 97  \w     97.00 142.00   1.00    5.00    --  111.00 -77.00  30.00   45
 98  \w    141.00 167.00   1.00    5.00    --  111.00  30.00 150.00   26
 99  \w    103.00 131.00   1.00    5.00    --  111.00  30.00 150.00   28
100  \w    113.00 138.00   1.00    5.00    --  111.00 -61.00 -90.00   25
101  \w     83.00 114.00   1.00    5.00    --  111.00  61.00 120.00   31
102  \w     77.00 106.00   1.00    5.00    --  111.00 -94.00-120.00   29
103  \w     93.00 156.00   1.00    5.00    --  111.00  45.00  90.00   63
104  \w     63.00  89.00   1.00    5.00    --  111.00 -61.00 -90.00   26
105  \w     83.00 112.00   1.00    5.00    --  111.00-125.00-150.00   29
106  \w     33.00  75.00   1.00    5.00    --  111.00 -94.00 -90.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0409671000
_diffrn_orient_matrix_UB_12      -0.0402491000
_diffrn_orient_matrix_UB_13      -0.0620085000
_diffrn_orient_matrix_UB_21      0.0195798000
_diffrn_orient_matrix_UB_22      0.0770939000
_diffrn_orient_matrix_UB_23      -0.0474913000
_diffrn_orient_matrix_UB_31      0.0203491000
_diffrn_orient_matrix_UB_32      0.0068074000
_diffrn_orient_matrix_UB_33      0.1704811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 1.0000
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            28858
_diffrn_reflns_point_group_measured_fraction_full 0.9926
_diffrn_reflns_point_group_measured_fraction_max 0.9880
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.74
_diffrn_reflns_theta_min         5.72
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           40.0
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (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    1.403
_exptl_crystal_description       blade
_exptl_crystal_F_000             2006.594
_exptl_crystal_recrystallization_method
'The material was recrystallised from DMSO by slow cooling'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.1538
_refine_diff_density_min         -0.1192
_refine_diff_density_rms         0.0323
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_d_res_high            0.7954
_refine_ls_d_res_low             7.7391
_refine_ls_goodness_of_fit_ref   1.0588
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.0496
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0561P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.974
_reflns_limit_h_max              38
_reflns_limit_h_min              -38
_reflns_limit_k_max              22
_reflns_limit_k_min              -21
_reflns_limit_l_max              10
_reflns_limit_l_min              -9
_reflns_number_gt                2268
_reflns_number_total             2312
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4sc02755h2.cif
_cod_data_source_block           NM21005
_cod_depositor_comments
'Adding full bibliography for 1572402--1572407.cif.'
_cod_original_sg_symbol_Hall     ' F 2 -2d'
_cod_database_code               1572402
_publ_section_exptl
;
Any special experimental details
;
_chemical_oxdiff_formula         C32H26O4
_chemical_oxdiff_usercomment     '@ 120 K K53B9'
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 C11, H11a, H11b, H11c
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, H12a, H12b, H12c
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id K53B9
_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 4.011
_oxdiff_exptl_absorpt_empirical_full_min 0.507