Chiral cyclic [n]spirobifluorenylenes: carbon nanorings consisting of helically arranged quaterphenyl rods illustrating partial units of woven patterns
Zhu, Kaige KZ; Kamochi, Kosuke KK; Kodama, Takuya; Tobisu, Mamoru; Amaya, Toru; Chemical Science  (2020) –; doi:10.1039/D0SC02452J

data_1558857
_publ_section_title
;
 Chiral cyclic [n]spirobifluorenylenes: carbon nanorings consisting of
 helically arranged quaterphenyl rods illustrating partial units of woven
 patterns
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02452J
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H13'
_chemical_formula_sum            'C25 H13'
_chemical_formula_weight         313.35
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc24v719
_audit_creation_date             2020-08-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-12 deposited with the CCDC.	2020-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   25.07149(13)
_cell_length_b                   25.07149(13)
_cell_length_c                   11.09028(7)
_cell_measurement_reflns_used    53944
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.2510
_cell_measurement_theta_min      3.4840
_cell_volume                     6037.17(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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     33.00  62.00   0.50    0.84    --   42.80 -29.00  42.00   58
  2  \w     25.00  50.00   0.50    3.35    --   76.50 -29.00  42.00   50
  3  \w     52.00  78.00   0.50    0.84    --   42.80  57.00 -90.00   52
  4  \w     66.00  93.00   0.50    0.84    --   42.80  77.00 -60.00   54
  5  \w     74.00 136.00   0.50    3.35    --   62.00  82.00  14.13  124
  6  \w    114.00 139.00   0.50    3.35    --   70.00  82.00  40.64   50
  7  \w     92.00 149.00   0.50    3.35    --   76.50  77.00 -60.00  114
  8  \w    104.00 129.00   0.50    3.35    --   76.50  29.00-156.00   50
  9  \w     48.00  73.00   0.50    3.35    --   76.50  77.00-150.00   50
 10  \w     42.00  68.00   0.50    3.35    --   70.00  78.00-113.43   52
 11  \w     48.00  80.00   0.50    3.35    --   76.50  77.00 -90.00   64
 12  \w     49.00  86.00   0.50    3.35    --   76.50  77.00 -60.00   74
 13  \w     46.00  81.00   0.50    3.35    --   74.00  78.00  10.73   70
 14  \w     50.00  80.00   0.50    3.35    --   76.50  77.00  60.00   60
 15  \w     80.00 114.00   0.50    0.84    --   42.80  57.00  90.00   68
 16  \w     48.00  96.00   0.50    3.35    --   76.50  77.00 150.00   96
 17  \w     39.00  65.00   0.50    3.35    --   70.00  82.00  40.64   52
 18  \w     48.00  74.00   0.50    3.35    --   76.50  77.00  90.00   52
 19  \w     48.00  74.00   0.50    3.35    --   76.50  77.00 109.29   52
 20  \w     31.00  56.00   0.50    3.35    --   62.00  83.00  81.20   50
 21  \w     21.00  49.00   0.50    0.84    --   42.80  57.00  90.00   56
 22  \w     18.00  43.00   0.50    0.84    --   54.00  92.00 140.95   50
 23  \w     31.00  75.00   0.50    3.35    --   62.00  82.00 156.93   88
 24  \w     40.00  70.00   0.50    3.35    --   70.00  81.00 174.32   60
 25  \w     20.00  45.00   0.50    0.84    --   54.00  89.00  84.50   50
 26  \w      3.00  41.00   0.50    0.84    --   38.00  91.00 121.26   76
 27  \w     20.00  45.00   0.50    0.84    --   54.00  88.00  18.53   50
 28  \w     31.00  61.00   0.50    3.35    --   62.00  82.00  14.13   60
 29  \w     48.00  80.00   0.50    3.35    --   76.50  77.00 -30.00   64
 30  \w     31.00  63.00   0.50    3.35    --   62.00  83.00 -54.27   64
 31  \w     22.00 114.00   0.50    0.84    --   42.80  29.00-156.00  184
 32  \w     21.00  51.00   0.50    0.84    --   42.80  57.00 -90.00   60
 33  \w     20.00  45.00   0.50    0.84    --   54.00  89.00 -98.44   50
 34  \w     14.00  39.00   0.50    0.84    --   42.80  77.00 -60.00   50
 35  \w     16.00  41.00   0.50    0.84    --   50.00  89.00 -72.18   50
 36  \w     20.00  45.00   0.50    0.84    --   54.00  89.00 -38.47   50
 37  \w     21.00  46.00   0.50    0.84    --   54.00  89.00-168.75   50
 38  \w    -21.00  16.00   0.50    0.84    --   42.80 -29.00  42.00   74
 39  \w    -74.00 -21.00   0.50    0.84    --  -42.80 -29.00  42.00  106
 40  \w    -48.00 -20.00   0.50    0.84    --  -42.80 -57.00 -30.00   56
 41  \w    -78.00 -53.00   0.50    3.35    -- -106.00  29.00-156.00   50
 42  \w    -64.00 -38.00   0.50    3.35    -- -106.00  57.00-150.00   52
 43  \w    -77.00 -51.00   0.50    3.35    -- -106.00  91.00 -80.70   52
 44  \w    -76.00 -50.00   0.50    3.35    -- -106.00 125.00 -60.00   52
 45  \w    -87.00 -47.00   0.50    3.35    -- -106.00  77.00 -30.00   80
 46  \w    -18.00  29.00   0.50    0.84    --  -42.80  29.00-156.00   94
 47  \w    -92.00 -66.00   0.50    0.84    --  -42.80 -57.00 -30.00   52
 48  \w    -98.00 -56.00   0.50    3.35    --  -86.00 -83.00  -8.97   84
 49  \w    -92.00 -62.00   0.50    3.35    --  -90.00 -75.00  26.41   60
 50  \w    -82.00 -54.00   0.50    3.35    --  -82.00 -75.00  93.89   56
 51  \w    -80.00 -53.00   0.50    3.35    --  -82.00 -76.00 178.90   54
 52  \w    -84.00 -58.00   0.50    3.35    --  -90.00 -83.00 164.66   52
 53  \w    -89.00 -61.00   0.50    3.35    --  -90.00 -76.00 131.37   56
 54  \w    -97.00 -63.00   0.50    3.35    --  -90.00 -71.00  61.25   68
 55  \w    -97.00 -71.00   0.50    3.35    --  -94.00 -66.00  82.57   52
 56  \w   -101.00 -72.00   0.50    3.35    --  -94.00 -73.00  22.38   58
 57  \w    -95.00 -69.00   0.50    3.35    --  -98.00 -76.00  58.79   52
 58  \w   -100.00 -75.00   0.50    3.35    -- -106.00 -81.00 101.13   50
 59  \w   -102.00 -77.00   0.50    3.35    -- -106.00 -76.00 162.28   50
 60  \w   -111.00 -77.00   0.50    3.35    -- -106.00 -76.00 148.09   68
 61  \w   -109.00 -77.00   0.50    3.35    -- -106.00 -79.00  90.05   64
 62  \w   -106.00 -73.00   0.50    3.35    -- -102.00 -76.00  57.77   66
 63  \w   -117.00 -78.00   0.50    3.35    -- -106.00 -75.00  14.60   78
 64  \w   -108.00 -80.00   0.50    3.35    -- -106.00 -77.00  30.00   56
 65  \w   -109.00 -67.00   0.50    3.35    --  -94.00 -73.00 -42.62   84
 66  \w   -103.00 -65.00   0.50    3.35    --  -94.00 -76.00 -60.44   76
 67  \w    -80.00 -48.00   0.50    0.84    --  -74.00 -71.00-141.68   64
 68  \w    -86.00 -53.00   0.50    3.35    --  -82.00 -76.00-138.89   66
 69  \w    -93.00 -67.00   0.50    3.35    --  -94.00 -74.00-154.22   52
 70  \w    -95.00 -69.00   0.50    3.35    --  -98.00 -76.00-132.59   52
 71  \w   -100.00 -65.00   0.50    3.35    --  -94.00 -76.00 -87.55   70
 72  \w   -103.00 -76.00   0.50    3.35    -- -106.00 -91.00 -54.58   54
 73  \w   -112.00 -56.00   0.50    3.35    --  -86.00 -82.00 -89.23  112
 74  \w   -112.00 -71.00   0.50    3.35    --  -98.00 -71.00-109.58   82
 75  \w   -115.00 -78.00   0.50    3.35    -- -106.00 -77.00-150.00   74
 76  \w   -126.00 -76.00   0.50    3.35    -- -106.00 -79.00-111.83  100
 77  \w   -133.00 -85.00   0.50    3.35    -- -106.00 -60.00-160.95   96
 78  \w   -126.00 -79.00   0.50    3.35    -- -106.00 -74.00 -91.75   94
 79  \w   -118.00 -77.00   0.50    3.35    -- -106.00 -76.00   4.77   82
 80  \w   -132.00-106.00   0.50    3.35    -- -106.00 -81.00 101.13   52
 81  \w   -125.00 -76.00   0.50    3.35    -- -106.00 -79.00 131.58   98
 82  \w   -115.00 -76.00   0.50    3.35    -- -106.00 -80.00 116.64   78
 83  \w   -108.00 -83.00   0.50    0.84    --  -42.80 -29.00  42.00   50
 84  \w    -95.00 -10.00   0.50    0.84    --  -42.80 125.00   0.00  170
 85  \w    -96.00 -13.00   0.50    0.84    --  -42.80 125.00 -60.00  166
 86  \w   -107.00 -65.00   0.50    3.35    -- -106.00 125.00  30.00   84
 87  \w   -117.00 -84.00   0.50    3.35    -- -106.00 125.00 -60.00   66
 88  \w   -118.00 -68.00   0.50    3.35    -- -106.00  77.00   0.00  100
 89  \w   -116.00 -32.00   0.50    3.35    -- -106.00 125.00 -30.00  168
 90  \w   -117.00 -60.00   0.50    3.35    -- -106.00 125.00 120.00  114
 91  \w   -108.00 -73.00   0.50    3.35    -- -106.00 125.00 150.00   70
 92  \w   -134.00 -33.00   0.50    3.35    -- -106.00  77.00 150.00  202
 93  \w   -131.00 -98.00   0.50    3.35    -- -106.00  77.00 -30.00   66
 94  \w   -139.00-102.00   0.50    3.35    -- -106.00  91.00 -80.70   74
 95  \w   -121.00 -87.00   0.50    3.35    -- -106.00  57.00-150.00   68
 96  \w   -117.00 -32.00   0.50    3.35    -- -106.00 125.00-180.00  170
 97  \w   -158.00 -83.00   0.50    3.35    -- -106.00 -29.00  42.00  150
 98  \w   -151.00-125.00   0.50    3.35    --  -82.00 -75.00  93.89   52
 99  \w   -156.00-126.00   0.50    3.35    -- -106.00 -79.00  90.05   60
100  \w   -162.00-137.00   0.50    3.35    --  -90.00 -75.00  26.41   50
101  \w   -149.00 -70.00   0.50    3.35    --  -94.00 -66.00  -4.64  158
102  \w   -150.00-124.00   0.50    3.35    --  -98.00 -76.00-132.59   52
103  \w   -137.00 -81.00   0.50    3.35    -- -106.00 -72.00-172.94  112
104  \w   -162.00 -81.00   0.50    3.35    -- -106.00 -75.00 -22.92  162
105  \w   -159.00-134.00   0.50    3.35    --  -90.00 -71.00  61.25   50
106  \w   -155.00-129.00   0.50    3.35    -- -106.00 -75.00  14.60   52
107  \w   -159.00 -76.00   0.50    3.35    -- -106.00 -78.00  -5.01  166
108  \w   -150.00 -83.00   0.50    3.35    -- -106.00 -77.00 -30.00  134
109  \w   -163.00-138.00   0.50    3.35    -- -106.00 -60.00-160.95   50
110  \w   -156.00 -93.00   0.50    3.35    -- -106.00 -99.00-180.00  126
111  \w   -170.00 -79.00   0.50    3.35    -- -106.00 -77.00-120.00  182
112  \w   -171.00-145.00   0.50    3.35    -- -106.00 -77.00-150.00   52
113  \w   -176.00-138.00   0.50    3.35    -- -106.00 -74.00 -91.75   76
114  \w   -177.00 -82.00   0.50    3.35    -- -106.00 -66.00 -54.82  190
115  \w   -166.00 -76.00   0.50    3.35    -- -106.00 -78.00  57.84  180
116  \w   -145.00-120.00   0.50    3.35    --  -90.00 -83.00 164.66   50
117  \w   -175.00-135.00   0.50    3.35    -- -106.00 -79.00 131.58   80
118  \w   -176.00-124.00   0.50    3.35    -- -106.00 -76.00 162.28  104
119  \w   -165.00 -79.00   0.50    3.35    -- -106.00 -71.00  35.61  172
120  \w   -166.00-141.00   0.50    3.35    -- -106.00 -77.00  30.00   50
121  \w   -174.00-149.00   0.50    3.35    -- -106.00 -91.00 -54.58   50
122  \w   -168.00 -78.00   0.50    3.35    -- -106.00 -75.00 -84.24  180
123  \w   -175.00 -83.00   0.50    3.35    -- -106.00 -99.00-150.00  184
124  \w   -173.00-147.00   0.50    3.35    -- -106.00 -80.00 116.64   52
125  \w   -156.00-119.00   0.50    3.35    -- -106.00 -99.00 150.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            67316
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.272
_diffrn_reflns_theta_min         3.526
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    0.776
_exptl_crystal_description       block
_exptl_crystal_F_000             1467
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene and MeOH'
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 2674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.47(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5442
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0593
_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^)+(0.1286P)^2^+3.2784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.1699
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5419
_reflns_number_total             5442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02452j2.cif
_cod_data_source_block           190418_zkg_76_trimer_sss
_cod_original_cell_volume        6037.17(7)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               1558857
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C23(H23), C4(H4), C17(H17), C6(H6), C12(H12), C24(H24), C13(H13),
 C5(H5), C7(H7), C22(H22), C16(H16), C21(H21)
;
_shelx_res_checksum              69239
_shelx_fab_checksum              24697
_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
;