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_1568666
_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         'C60, C72 H54'
_chemical_formula_sum            'C132 H54'
_chemical_formula_weight         1639.75
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-06
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-01-07 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.3460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4705(2)
_cell_length_b                   18.02860(10)
_cell_length_c                   26.3919(3)
_cell_measurement_reflns_used    39448
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      77.4740
_cell_measurement_theta_min      2.3790
_cell_volume                     9113.61(15)
_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      172.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_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    -71.00  11.00   0.50    1.00    --  -48.14  89.00 153.00  164
  2  \w    -23.00  74.00   0.50    1.00    --   48.14 -89.00  38.00  194
  3  \w   -168.00 -80.00   0.50    5.00    -- -104.00 -89.00  38.00  176
  4  \w   -104.00 -73.00   0.50    5.00    -- -104.00  89.00 153.00   62
  5  \w     87.00 177.00   0.50    5.00    --  106.93  89.00 153.00  180
  6  \w     46.00  71.00   0.50    5.00    --  106.93 -89.00  38.00   50
  7  \w   -120.00 -73.00   0.50    1.00    --  -48.14-125.00  90.00   94
  8  \w    -24.00   3.00   0.50    1.00    --  -48.14  19.00 -60.00   54
  9  \w    -23.00  22.00   0.50    1.00    --  -48.14  19.00 -30.00   90
 10  \w    -13.00  27.00   0.50    1.00    --   48.14 -19.00 120.00   80
 11  \w    -19.00  14.00   0.50    1.00    --   48.14 -19.00  60.00   66
 12  \w     -4.00  23.00   0.50    1.00    --   48.14 -38.00  30.00   54
 13  \w    -18.00  28.00   0.50    1.00    --   48.14 -19.00 -30.00   92
 14  \w     58.00  89.00   0.50    1.00    --   48.14-125.00-150.00   62
 15  \w    -21.00  28.00   0.50    1.00    --   48.14 -19.00  90.00   98
 16  \w    -61.00 -36.00   0.50    5.00    -- -104.00  57.00 120.00   50
 17  \w   -171.00-114.00   0.50    5.00    -- -104.00 -38.00-120.00  114
 18  \w   -153.00 -94.00   0.50    5.00    -- -104.00 -38.00  60.00  118
 19  \w    -63.00 -33.00   0.50    5.00    -- -104.00 113.00 121.68   60
 20  \w   -108.00 -70.00   0.50    5.00    -- -104.00 113.00 121.68   76
 21  \w   -153.00 -87.00   0.50    5.00    -- -104.00 -99.00 150.00  132
 22  \w     37.00  67.00   0.50    5.00    --  106.93 -99.00 -90.00   60
 23  \w     96.00 175.00   0.50    5.00    --  106.93  38.00 -60.00  158
 24  \w     72.00  98.00   0.50    5.00    --  106.93 -99.00-150.00   52
 25  \w     38.00 101.00   0.50    5.00    --  106.93 -99.00 150.00  126
 26  \w     35.00 106.00   0.50    5.00    --  106.93 -99.00   0.00  142
 27  \w     36.00  71.00   0.50    5.00    --  106.93 -99.00-150.00   70
 28  \w     99.00 167.00   0.50    5.00    --  106.93  38.00-120.00  136
 29  \w     35.00 108.00   0.50    5.00    --  106.93-109.00  70.20  146
 30  \w     38.00  68.00   0.50    5.00    --  106.93 -57.00  60.00   60
 31  \w     35.00  63.00   0.50    5.00    --  106.93 -57.00 -90.00   56
 32  \w     52.00  80.00   0.50    5.00    --  106.93-125.00 150.00   56
 33  \w     53.00  99.00   0.50    5.00    --  106.93 -99.00-120.00   92
 34  \w    120.00 167.00   0.50    5.00    --  106.93  19.00 -30.00   94
 35  \w     91.00 121.00   0.50    5.00    --  106.93-138.00  35.26   60
 36  \w     77.00 111.00   0.50    5.00    --  106.93-125.00 -60.00   68
 37  \w     62.00 105.00   0.50    5.00    --  106.93 -99.00-180.00   86
 38  \w     41.00 111.00   0.50    5.00    --  106.93-125.00 -30.00  140
 39  \w     80.00 105.00   0.50    5.00    --  106.93 -99.00  60.00   50
 40  \w    111.00 175.00   0.50    5.00    --  106.93  38.00 120.00  128
 41  \w     36.00  95.00   0.50    5.00    --  106.93-125.00   0.00  118
 42  \w     36.00  65.00   0.50    5.00    --  106.93 -57.00-180.00   58
;
_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      0.0793452000
_diffrn_orient_matrix_UB_12      0.0114743000
_diffrn_orient_matrix_UB_13      0.0050410000
_diffrn_orient_matrix_UB_21      -0.0115603000
_diffrn_orient_matrix_UB_22      0.0374829000
_diffrn_orient_matrix_UB_23      -0.0533276000
_diffrn_orient_matrix_UB_31      -0.0063842000
_diffrn_orient_matrix_UB_32      0.0759245000
_diffrn_orient_matrix_UB_33      0.0255084000
_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  0.0586
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            122024
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.844
_diffrn_reflns_theta_min         2.307
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41165
_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 intense brown'
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       needle
_exptl_crystal_F_000             3384
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.191
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1202
_refine_ls_number_reflns         18975
_refine_ls_number_restraints     270
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0769
_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^)+(0.1363P)^2^+3.9605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2206
_refine_ls_wR_factor_ref         0.2338
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14668
_reflns_number_total             18975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00658a2.cif
_cod_data_source_block           d31c60
_cod_depositor_comments
'Adding full bibliography for 1568662--1568666.cif.'
_cod_database_code               1568666
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H'
_chemical_oxdiff_usercomment     'C H'
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.898
_olex2_refinement_description
;
1. Rigid bond restraints
 C27, C1, C2, C6, C7, C3, C8, C5, C12, C13, C14, C4, C9, C15, C16, C11, C21,
 C30, C22, C10, C17, C23, C24, C19, C20, C29, C31, C39, C32, C18, C25, C33, C34,
  C28, C38, C41, C40, C42, C26, C35, C43, C44, C36, C37, C50, C54, C51, C55,
 C45, C60, C47, C48, C49, C53, C52, C56, C46, C59, C57, C58
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C39, C40
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
2.a Aromatic/amide H refined with riding coordinates:
 C63(H63), C64(H64), C65(H65), C68(H68), C69(H69), C72(H72), C73(H73),
 C74(H74), C98(H98), C99(H99), C101(H101), C108(H108), C110(H110), C115(H115),
 C117(H117), C124(H124), C126(H126), C127(H127)
2.b Idealised Me refined as rotating group:
 C104(H10A,H10B,H10C), C105(H10D,H10E,H10F), C106(H10G,H10H,H10I), C112(H11A,
 H11B,H11C), C113(H11D,H11E,H11F), C114(H11G,H11H,H11I), C120(H12A,H12B,H12C),
 C121(H12D,H12E,H12F), C122(H12G,H12H,H12I), C130(H13A,H13B,H13C), C131(H13D,
 H13E,H13F), C132(H13G,H13H,H13I)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              94046
_shelx_fab_checksum              59314
_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 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.489