Buckybowl and its chiral hybrids featuring eight-membered rings and helicene units.
Duan, Yuxiao; Chen, Meng; Hayashi, Hironobu; Yamada, Hiroko; Liu, Xinyue; Zhang, Lei; Chemical science 14 (2023) 10420–10428; doi:10.1039/d3sc00658a

data_1568665
_publ_section_title
;
 Buckybowl and its chiral hybrids featuring eight-membered rings and
 helicene units.
;
_journal_issue                   38
_journal_name_full               'Chemical science'
_journal_page_first              10420
_journal_page_last               10428
_journal_paper_doi               10.1039/d3sc00658a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C72 H56'
_chemical_formula_sum            'C72 H56'
_chemical_formula_weight         921.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-04
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-09-19 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                101.227(2)
_cell_angle_beta                 95.079(3)
_cell_angle_gamma                100.078(3)
_cell_formula_units_Z            4
_cell_length_a                   12.6634(6)
_cell_length_b                   19.4621(6)
_cell_length_c                   22.1410(6)
_cell_measurement_reflns_used    13455
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      65.3630
_cell_measurement_theta_min      4.2290
_cell_volume                     5227.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.961
_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    -45.00   9.00   0.50    3.00    --   43.40  46.00 -60.00  108
  2  \w     81.00 114.00   0.50    3.00    --   43.40  46.00 -60.00   66
  3  \w     87.00 116.00   0.50    3.00    --   43.40   0.00-180.00   58
  4  \w    -22.00  79.00   0.50    3.00    --   43.40   0.00-180.00  202
  5  \w    -46.00 133.00   0.50    3.00    --   43.40  46.00  90.00  358
  6  \w     97.00 132.00   0.50    3.00    --   43.40  55.00 120.00   70
  7  \w    129.00 175.00   0.50   10.00    --   90.00  53.00  14.02   92
  8  \w     51.00 117.00   0.50   10.00    --   90.00  53.00  14.02  132
  9  \w      1.00  86.00   0.50   10.00    --   90.00  55.00  80.71  170
 10  \w     72.00 117.00   0.50   10.00    --   90.00  46.00 -30.00   90
 11  \w      4.00  40.00   0.50   10.00    --   90.00  18.00-120.00   72
 12  \w      2.00  91.00   0.50   10.00    --   90.00  46.00-180.00  178
 13  \w    118.00 175.00   0.50   10.00    --   90.00  46.00-180.00  114
 14  \w     17.00  63.00   0.50   10.00    --   90.00  46.00 -60.00   92
 15  \w     55.00 110.00   0.50   10.00    --   90.00  18.00 120.00  110
 16  \w      7.00  33.00   0.50   10.00    --   90.00  53.00  14.02   52
 17  \w     71.00 101.00   0.50   10.00    --   90.00  46.00 120.00   60
 18  \w    127.00 161.00   0.50   10.00    --   90.00  46.00-150.00   68
 19  \w    128.00 155.00   0.50   10.00    --   90.00  46.00 120.00   54
 20  \w      2.00  45.00   0.50   10.00    --   90.00  46.00 -30.00   86
 21  \w     63.00  88.00   0.50   10.00    --   90.00  28.00-180.00   50
 22  \w    139.00 178.00   0.50   10.00    --   90.00  46.00 -30.00   78
 23  \w    154.00 179.00   0.50   10.00    --   90.00  37.00 150.00   50
 24  \w    128.00 154.00   0.50   10.00    --   90.00  18.00-120.00   52
 25  \w    151.00 176.00   0.50   10.00    --   90.00  37.00 -30.00   50
 26  \w     29.00  55.00   0.50   10.00    --   90.00  46.00 150.00   52
 27  \w    132.00 177.00   0.50   10.00    --   90.00  46.00 150.00   90
 28  \w      3.00  29.00   0.50   10.00    --   90.00  46.00-120.00   52
 29  \w     85.00 110.00   0.50   10.00    --   90.00  46.00-120.00   50
 30  \w    141.00 178.00   0.50   10.00    --   90.00  46.00-120.00   74
 31  \w    136.00 178.00   0.50   10.00    --   90.00  43.00  53.19   84
 32  \w      5.00  43.00   0.50   10.00    --   90.00  37.00  30.00   76
 33  \w     80.00 178.00   0.50   10.00    --   90.00   0.00-180.00  196
 34  \w     71.00 100.00   0.50   10.00    --   90.00  46.00-150.00   58
 35  \w     78.00 106.00   0.50   10.00    --   90.00  37.00  30.00   56
 36  \w    116.00 178.00   0.50   10.00    --   90.00  37.00  30.00  124
 37  \w     24.00  53.00   0.50   10.00    --   90.00  28.00 -90.00   58
 38  \w    108.00 133.00   0.50   10.00    --   90.00  28.00 -90.00   50
 39  \w      2.00 100.00   0.50   10.00    --   90.00  18.00 150.00  196
 40  \w    127.00 153.00   0.50   10.00    --   90.00  18.00 150.00   52
 41  \w     12.00  45.00   0.50   10.00    --   90.00   9.00-150.00   66
 42  \w     82.00 107.00   0.50   10.00    --   90.00   9.00-150.00   50
 43  \w    147.00 178.00   0.50   10.00    --   90.00  46.00  90.00   62
 44  \w    128.00 153.00   0.50   10.00    --   90.00  28.00-180.00   50
 45  \w    119.00 164.00   0.50   10.00    --   90.00  37.00 -60.00   90
 46  \w      7.00  98.00   0.50   10.00    --   90.00  37.00 150.00  182
 47  \w     52.00  85.00   0.50   10.00    --   90.00  46.00  90.00   66
 48  \w      2.00  73.00   0.50   10.00    --   90.00  46.00  60.00  142
 49  \w     15.00  40.00   0.50   10.00    --   90.00  18.00-150.00   50
 50  \w     13.00  38.00   0.50   10.00    --   90.00  37.00-150.00   50
 51  \w    130.00 178.00   0.50   10.00    --   90.00  46.00 -60.00   96
 52  \w      4.00  40.00   0.50   10.00    --   90.00  43.00  53.19   72
 53  \w    104.00 179.00   0.50   10.00    --   90.00  55.00  80.71  150
 54  \w     78.00 178.00   0.50   10.00    --   90.00  55.00 -95.82  200
 55  \w      5.00  50.00   0.50   10.00    --   90.00  55.00 -95.82   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0080228000
_diffrn_orient_matrix_UB_12      -0.0342327000
_diffrn_orient_matrix_UB_13      0.0569999000
_diffrn_orient_matrix_UB_21      -0.0462229000
_diffrn_orient_matrix_UB_22      -0.0734698000
_diffrn_orient_matrix_UB_23      -0.0430510000
_diffrn_orient_matrix_UB_31      0.1153973000
_diffrn_orient_matrix_UB_32      -0.0143269000
_diffrn_orient_matrix_UB_33      -0.0034809000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17904
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.002
_diffrn_reflns_theta_max         67.002
_diffrn_reflns_theta_min         3.444
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.498
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       plate
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1413
_refine_ls_number_reflns         17904
_refine_ls_number_restraints     339
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0953
_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^)+(0.1352P)^2^+3.9884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2567
_refine_ls_wR_factor_ref         0.2838
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12107
_reflns_number_total             17904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00658a2.cif
_cod_data_source_block           dyx_tw_sq
_cod_depositor_comments
'Adding full bibliography for 1568662--1568666.cif.'
_cod_database_code               1568665
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHCl
_chemical_oxdiff_usercomment     CHCl
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.632(4)
 0.368(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C45-C43 = C1C-C43 = C73-C43 = C46-C43 = C1B-C43 = C44-C43
 1.54 with sigma of 0.01
 C71B-C69A = C70A-C69A = C70B-C69A = C72A-C69A = C72B-C69A = C71A-C69A
 1.54 with sigma of 0.01
 C1E-C69 = C71-C69 = C1D-C69 = C70-C69 = C74-C69 = C72-C69
 1.54 with sigma of 0.01
 C71B-C70B
 2.5 with sigma of 0.02
 C72B-C70B
 2.5 with sigma of 0.02
 C1E-C1D
 2.5 with sigma of 0.02
 C1D-C74
 2.5 with sigma of 0.02
 C71B-C72B
 2.5 with sigma of 0.02
 C1E-C74
 2.5 with sigma of 0.02
 C69A-C70A \\sim C69A-C70B
 with sigma of 0.02
 C43-C44 \\sim C43-C1B
 with sigma of 0.02
 C69-C70 \\sim C69-C1D
 with sigma of 0.02
 C43-C45 \\sim C43-C1C
 with sigma of 0.02
 C43-C46 \\sim C43-C73
 with sigma of 0.02
 C69A-C71A \\sim C69A-C71B
 with sigma of 0.02
 C69A-C72A \\sim C69A-C72B
 with sigma of 0.02
 C69-C71 \\sim C69-C1E
 with sigma of 0.02
 C69-C72 \\sim C69-C74
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C70A \\sim C71A \\sim C72A \\sim C72B \\sim C70B \\sim C71B \\sim C69A: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C69 \\sim C70 \\sim C71 \\sim C72 \\sim C74 \\sim C1D \\sim C1E: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C43 \\sim C44 \\sim C45 \\sim C46 \\sim C73 \\sim C1B \\sim C1C: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
Uanis(C70) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C74)
\\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(C1E) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C70A) \\sim Ueq, Uanis(C71A) \\sim Ueq, Uanis(C72A) \\sim Ueq,
Uanis(C72B) \\sim Ueq, Uanis(C70B) \\sim Ueq, Uanis(C71B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C73)
\\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1C) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
5. Others
 Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(H73C)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=
 Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=1-FVAR(1)
 Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=
 Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=FVAR(1)
 Sof(C72B)=Sof(H72G)=Sof(H72H)=Sof(H72I)=Sof(C70B)=Sof(H70G)=Sof(H70H)=
 Sof(H70I)=Sof(C71B)=Sof(H71G)=Sof(H71H)=Sof(H71I)=1-FVAR(2)
 Sof(C70A)=Sof(H70D)=Sof(H70E)=Sof(H70F)=Sof(C71A)=Sof(H71D)=Sof(H71E)=
 Sof(H71F)=Sof(C72A)=Sof(H72D)=Sof(H72E)=Sof(H72F)=FVAR(2)
 Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(H74C)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=
 Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(H1EC)=1-FVAR(3)
 Sof(C70)=Sof(H70A)=Sof(H70B)=Sof(H70C)=Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(H71C)=
 Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(H72C)=FVAR(3)
6.a Riding coordinates:
 C70B(H70G,H70H,H70I), C1D(H1DA,H1DB,H1DC)
6.b Aromatic/amide H refined with riding coordinates:
 C77(H77), C4(H4), C5(H5), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C38(H38), C39(H39), C41(H41), C42(H42), C47(H47), C48(H48), C50(H50), C55(H55),
  C57(H57), C65(H65), C66(H66), C68(H68), C3A(H3A), C4A(H4A), C5A(H5A),
 C8A(H8A), C9A(H9A), C12A(H12A), C13A(H13A), C14A(H14A), C38A(H38A), C39A(H39A),
  C41A(H41A), C42A(H42A), C47A(H47A), C48A(H48A), C50A(H50A), C55A(H55A),
 C57A(H57A), C65A(H65A), C66A(H66A), C68A(H68A)
6.c Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C52(H52A,H52B,
 H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C60(H60A,H60B,H60C), C61(H61A,
 H61B,H61C), C62(H62A,H62B,H62C), C70(H70A,H70B,H70C), C71(H71A,H71B,H71C),
 C72(H72A,H72B,H72C), C44A(H44D,H44E,H44F), C45A(H45D,H45E,H45F), C46A(H46D,
 H46E,H46F), C52A(H52D,H52E,H52F), C53A(H53D,H53E,H53F), C54A(H54D,H54E,H54F),
 C60A(H60D,H60E,H60F), C61A(H61D,H61E,H61F), C62A(H62D,H62E,H62F), C70A(H70D,
 H70E,H70F), C71A(H71D,H71E,H71F), C72A(H72D,H72E,H72F), C73(H73A,H73B,H73C),
 C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,H1CC), C72B(H72G,H72H,H72I), C71B(H71G,H71H,
 H71I), C74(H74A,H74B,H74C), C1E(H1EA,H1EB,H1EC)
;
_shelx_res_checksum              5112
_shelx_fab_checksum              4740
_platon_squeeze_void_probe_radius 1.20
_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 3.062
_oxdiff_exptl_absorpt_empirical_full_min 0.342