Tetrahomo corona[4]arene-based spirophanes: synthesis, structure, and properties.
Guo, Shen-Yi; Zhang, Zhuo-Ang; Tong, Shuo; Guo, Qing-Hui; Hua, Ruimao; Wang, Mei-Xiang; Chemical science 14 (2023) 8393–8400; doi:10.1039/d3sc02417b

data_1569499
_publ_section_title
;
 Tetrahomo corona[4]arene-based spirophanes: synthesis, structure, and
 properties.
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              8393
_journal_page_last               8400
_journal_paper_doi               10.1039/d3sc02417b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C64 H44 F8 N8 O10 S2, 1.5(C4 H8 O)'
_chemical_formula_sum            'C70 H56 F8 N8 O11.5 S2'
_chemical_formula_weight         1409.34
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-08 deposited with the CCDC.	2023-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                101.208(2)
_cell_angle_beta                 104.314(2)
_cell_angle_gamma                101.040(2)
_cell_formula_units_Z            1
_cell_length_a                   8.9270(2)
_cell_length_b                   13.6209(3)
_cell_length_c                   14.7225(3)
_cell_measurement_reflns_used    34586
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.6620
_cell_measurement_theta_min      3.1800
_cell_volume                     1646.58(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_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      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_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    -41.00  24.00   0.50    0.05    --  -48.14  38.00  90.00  130
  2  \w    -64.00  24.00   0.50    0.05    --  -48.14  62.00 -34.00  176
  3  \w    -71.00 -32.00   0.50    0.17    -- -104.00  62.00 -34.00   78
  4  \w    -61.00 -32.00   0.50    0.17    -- -104.00  57.00 -60.00   58
  5  \w    -41.00  24.00   0.50    0.05    --  -48.14  38.00-150.00  130
  6  \w    -23.00  27.00   0.50    0.05    --    8.00  97.00-177.14  100
  7  \w     -2.00  30.50   0.50    0.05    --   28.00  95.00-107.44   65
  8  \w     16.00  42.00   0.50    0.05    --   44.00  91.00-129.08   52
  9  \w    -13.00  17.50   0.50    0.05    --   20.00 101.00 -63.17   61
 10  \w    -22.00  13.50   0.50    0.05    --   12.00 102.00  58.17   71
 11  \w     27.00 120.00   0.50    0.05    --   48.14  77.00   0.00  186
 12  \w     40.00 131.00   0.50    0.05    --   60.00  74.00 -63.25  182
 13  \w     35.00 128.00   0.50    0.05    --   56.00  75.00 -97.73  186
 14  \w     36.00 128.00   0.50    0.05    --   56.00  74.00 -73.65  184
 15  \w     47.00  77.00   0.50    0.05    --   68.00  76.00   5.00   60
 16  \w     36.00 128.00   0.50    0.05    --   56.00  72.00  21.18  184
 17  \w     33.00 120.00   0.50    0.05    --   48.14  62.00 -34.00  174
 18  \w     34.00 128.00   0.50    0.05    --   56.00  77.00  40.91  188
 19  \w     36.00 128.00   0.50    0.05    --   56.00  74.00 120.23  184
 20  \w     40.00 131.00   0.50    0.05    --   60.00  72.00 148.80  182
 21  \w     91.00 178.00   0.50    0.17    --  106.93  62.00 -34.00  174
 22  \w     35.00  68.00   0.50    0.17    --  106.93 -57.00 -30.00   66
 23  \w     35.00  75.00   0.50    0.17    --  106.93 -62.00-171.00   80
 24  \w    -23.00  64.00   0.50    0.05    --   48.14 -62.00-171.00  174
 25  \w     36.00  97.00   0.50    0.17    --  106.93 -77.00  60.00  122
 26  \w     35.00 106.00   0.50    0.17    --  106.93 -99.00  60.00  142
 27  \w     36.00 103.00   0.50    0.17    --  106.93 -99.00   0.00  134
 28  \w     43.00  75.00   0.50    0.17    --  106.93-125.00 -60.00   64
 29  \w     35.00  91.00   0.50    0.17    --  106.93 -99.00-180.00  112
 30  \w     50.00 109.00   0.50    0.17    --  106.93-125.00   0.00  118
 31  \w     43.00 108.00   0.50    0.17    --  106.93-109.00 178.17  130
 32  \w    -72.00 -36.00   0.50    0.17    -- -104.00 147.00 165.73   72
 33  \w   -128.00 -80.00   0.50    0.17    -- -104.00 147.00 165.73   96
 34  \w   -102.00 -32.00   0.50    0.17    -- -104.00 125.00  90.00  140
 35  \w    -94.00 -63.00   0.50    0.17    -- -104.00 142.00 -16.55   62
 36  \w   -124.00 -98.00   0.50    0.17    -- -104.00 142.00 -16.55   52
 37  \w   -108.00 -68.00   0.50    0.17    -- -104.00 111.00 -85.48   80
 38  \w   -165.00 -82.00   0.50    0.17    -- -104.00 -80.00 -70.46  166
 39  \w   -175.00 -81.00   0.50    0.17    -- -104.00 -79.00 -36.49  188
 40  \w    -97.00 -62.00   0.50    0.17    --  -84.00 -77.00 -92.59   70
 41  \w    -76.00 -50.00   0.50    0.05    --  -72.00 -77.00-170.04   52
 42  \w   -139.00 -70.00   0.50    0.17    --  -92.00 -77.00 -14.65  138
 43  \w    -76.00 -50.00   0.50    0.05    --  -72.00 -77.00 -24.89   52
 44  \w   -127.00 -35.00   0.50    0.05    --  -56.00 -76.00 -62.20  184
 45  \w    -79.00 -53.00   0.50    0.05    --  -72.00 -75.00 -51.76   52
 46  \w   -114.00 -68.00   0.50    0.17    --  -88.00 -75.00  24.80   92
 47  \w    -76.00 -50.00   0.50    0.05    --  -72.00 -77.00  88.45   52
 48  \w   -123.00 -30.00   0.50    0.05    --  -52.00 -77.00 151.86  186
 49  \w   -123.00 -31.00   0.50    0.05    --  -52.00 -76.00  92.99  184
 50  \w    -89.00 -63.00   0.50    0.17    --  -84.00 -75.00  27.10   52
 51  \w   -126.00-100.00   0.50    0.05    --  -76.00 -74.00 135.77   52
 52  \w    -81.00 -55.00   0.50    0.05    --  -76.00 -74.00 135.77   52
 53  \w   -149.00-111.00   0.50    0.17    --  -88.00 -74.00   0.35   76
 54  \w    -95.00 -68.00   0.50    0.17    --  -88.00 -74.00   0.35   54
 55  \w    -94.00 -68.00   0.50    0.17    --  -88.00 -75.00 -48.92   52
 56  \w    -81.00 -55.00   0.50    0.05    --  -76.00 -74.00-138.21   52
 57  \w    -90.00 -63.00   0.50    0.17    --  -84.00 -74.00-117.91   54
 58  \w   -142.00-116.00   0.50    0.17    --  -84.00 -74.00-117.91   52
 59  \w    -70.00 -44.00   0.50    0.05    --  -64.00 -73.00-147.45   52
 60  \w    -88.00 -63.00   0.50    0.17    --  -84.00 -74.00 -66.31   50
 61  \w    -85.00 -60.00   0.50    0.17    --  -80.00 -73.00 -86.67   50
 62  \w   -100.00 -64.00   0.50    0.17    --  -84.00 -73.00 -18.22   72
 63  \w    -90.00 -64.00   0.50    0.17    --  -84.00 -73.00  55.55   52
 64  \w   -159.00-114.00   0.50    0.17    --  -88.00 -73.00  44.20   90
 65  \w   -106.00 -68.00   0.50    0.17    --  -88.00 -73.00  44.20   76
 66  \w    -84.00 -59.00   0.50    0.17    --  -80.00 -74.00 122.19   50
 67  \w    -93.00 -68.00   0.50    0.17    --  -88.00 -72.00  98.50   50
 68  \w   -123.00 -68.00   0.50    0.17    --  -88.00 -73.00 177.91  110
 69  \w    -93.00 -64.00   0.50    0.17    --  -84.00 -72.00 159.04   58
 70  \w   -160.00-126.00   0.50    0.17    --  -88.00 -72.00  98.50   68
 71  \w   -151.00-125.00   0.50    0.17    --  -80.00 -74.00 122.19   52
 72  \w   -131.00 -40.00   0.50    0.05    --  -60.00 -73.00 163.36  182
 73  \w    -93.00 -64.00   0.50    0.17    --  -84.00 -72.00  77.67   58
 74  \w    -75.00 -49.00   0.50    0.05    --  -68.00 -70.00  45.24   52
 75  \w    -76.00 -49.00   0.50    0.05    --  -68.00 -70.00 136.58   54
 76  \w    -79.00 -49.00   0.50    0.05    --  -68.00 -70.00  21.66   60
 77  \w   -165.00 -86.00   0.50    0.17    -- -104.00 -69.00  55.37  158
 78  \w   -156.00 -85.00   0.50    0.17    -- -104.00 -69.00 -63.40  142
 79  \w   -120.00 -78.00   0.50    0.17    --  -96.00 -67.00-128.96   84
 80  \w   -172.00 -85.00   0.50    0.17    -- -104.00 -70.00-112.44  174
 81  \w   -168.00 -85.00   0.50    0.17    -- -104.00 -70.00-150.60  166
 82  \w    -96.00 -70.00   0.50    0.17    --  -88.00 -67.00-146.09   52
 83  \w    -94.00 -66.00   0.50    0.17    --  -84.00 -67.00-173.39   56
 84  \w   -163.00-125.00   0.50    0.17    --  -96.00 -67.00-128.96   76
 85  \w   -175.00 -88.00   0.50    0.17    -- -104.00 -62.00-171.00  174
 86  \w   -156.00 -71.00   0.50    0.17    --  -88.00 -65.00 -52.52  170
 87  \w   -120.00 -32.00   0.50    0.05    --  -48.14 -62.00-171.00  176
 88  \w   -168.00 -81.00   0.50    0.17    --  -96.00 -65.00  10.00  174
 89  \w   -133.00-107.00   0.50    0.17    --  -96.00 -67.00 123.52   52
 90  \w   -106.00 -78.00   0.50    0.17    --  -96.00 -67.00 123.52   56
 91  \w   -102.00 -77.00   0.50    0.17    --  -92.00 -61.00 126.28   50
 92  \w    -93.00 -67.00   0.50    0.17    --  -80.00 -58.00 160.43   52
 93  \w   -158.00 -79.00   0.50    0.17    --  -92.00 -61.00 102.62  158
 94  \w   -142.00 -87.00   0.50    0.17    -- -100.00 -57.00  75.84  110
 95  \w   -152.00-111.00   0.50    0.17    --  -92.00 -61.00 126.28   82
 96  \w   -170.00 -80.00   0.50    0.17    -- -100.00 -81.00 169.97  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1393431000
_diffrn_orient_matrix_UB_12      0.0712360000
_diffrn_orient_matrix_UB_13      -0.0186038000
_diffrn_orient_matrix_UB_21      0.0055825000
_diffrn_orient_matrix_UB_22      -0.0898247000
_diffrn_orient_matrix_UB_23      -0.0798048000
_diffrn_orient_matrix_UB_31      -0.1201036000
_diffrn_orient_matrix_UB_32      0.0324547000
_diffrn_orient_matrix_UB_33      -0.0758489000
_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  0.0777
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            58642
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.402
_diffrn_reflns_theta_min         3.203
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.526
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 5002 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     919
_refine_ls_number_reflns         12534
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0570
_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^)+(0.1706P)^2^+0.0093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.1726
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                11713
_reflns_number_total             12534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02417b2.cif
_cod_data_source_block           25aa_auto
_cod_depositor_comments
'Adding full bibliography for 1569486--1569506.cif.'
_cod_original_formula_sum        'C70 H56 F8 N8 O11.50 S2'
_cod_database_code               1569499
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F N S'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: O1(0.5) C5(0.5) H5A(0.5) H5B(0.5) C28(0.5) H28A(0.5) H28B(0.5)
 C14(0.5) H14A(0.5) H14B(0.5) C19(0.5) H19A(0.5) H19B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C73(H73A,H73B), C62(H62A,H62B), C82(H82A,H82B), C13(H13A,
 H13B), C59(H59A,H59B), C35(H35A,H35B), C6(H6A,H6B), C40(H40A,H40B), C56(H56A,
 H56B), C27(H27A,H27B), C97(H97A,H97B), C49(H49A,H49B), C95(H95A,H95B),
 C96(H96A,H96B), C94(H94A,H94B), C5(H5A,H5B), C28(H28A,H28B), C14(H14A,H14B),
 C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C42(H42), C3(H3), C9(H9), C8(H8), C22(H22), C45(H45), C25(H25), C30(H30),
 C10(H10), C11(H11), C24(H24), C23(H23), C63(H63), C69(H69), C65(H65), C66(H66),
  C64(H64), C72(H72), C70(H70), C71(H71)
;
_shelx_res_checksum              51647
_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 2.399
_oxdiff_exptl_absorpt_empirical_full_min 0.514