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_1568662
_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         '3(C H Cl3), 2(C72 H60)'
_chemical_formula_sum            'C147 H123 Cl9'
_chemical_formula_weight         2208.50
_chemical_name_systematic        DYX-7
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-09-05 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                77.629(2)
_cell_angle_beta                 80.917(3)
_cell_angle_gamma                84.108(3)
_cell_formula_units_Z            2
_cell_length_a                   11.5164(5)
_cell_length_b                   17.9050(5)
_cell_length_c                   31.0340(10)
_cell_measurement_reflns_used    16633
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      71.2570
_cell_measurement_theta_min      2.4660
_cell_volume                     6156.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.952
_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    -22.00  23.00   0.50    0.80    --  -47.45  19.00 -60.00   90
  2  \w    -23.00  27.00   0.50    0.80    --  -47.45  19.00  30.00  100
  3  \w    -56.00 -27.00   0.50    3.50    --  -99.00  61.00 -90.00   58
  4  \w    -64.00 -27.00   0.50    3.50    --  -99.00  77.00-120.00   74
  5  \w    -64.00 -26.00   0.50    3.50    --  -99.00  61.00-180.00   76
  6  \w    -61.00 -34.00   0.50    3.50    --  -99.00 135.00 -61.76   54
  7  \w    -68.00 -43.00   0.50    3.50    --  -99.00  61.00 -30.00   50
  8  \w    -93.00 -26.00   0.50    0.80    --  -47.45 123.00  42.00  134
  9  \w    -82.00 -26.00   0.50    3.50    --  -99.00 141.00  71.86  112
 10  \w    -85.00 -60.00   0.50    3.50    --  -99.00 148.00 -31.21   50
 11  \w   -103.00 -26.00   0.50    3.50    --  -99.00 123.00  42.00  154
 12  \w   -109.00 -83.00   0.50    3.50    --  -99.00 125.00 -60.00   52
 13  \w   -127.00 -96.00   0.50    3.50    --  -99.00 148.00 -31.21   62
 14  \w   -119.00 -81.00   0.50    3.50    --  -99.00 135.00 -61.76   76
 15  \w   -106.00 -70.00   0.50    0.80    --  -47.45 148.00-153.00   72
 16  \w     68.00 118.00   0.50    0.80    --   47.45 148.00-153.00  100
 17  \w     79.00 117.00   0.50    3.50    --  103.25 148.00-153.00   76
 18  \w     91.00 169.00   0.50    3.50    --  103.25  45.00-150.00  156
 19  \w    135.00 161.00   0.50    3.50    --  103.25  45.00 -60.00   52
 20  \w    105.00 131.00   0.50    3.50    --  103.25  45.00 -60.00   52
 21  \w     82.00 169.00   0.50    3.50    --  103.25 123.00  42.00  174
 22  \w     91.00 166.00   0.50    3.50    --  103.25  30.00 150.00  150
 23  \w     59.00 109.00   0.50    3.50    --  103.25 -77.00 -30.00  100
 24  \w     71.00  96.00   0.50    3.50    --  103.25-123.00 -37.00   50
 25  \w     60.00 110.00   0.50    3.50    --  103.25-125.00 -90.00  100
 26  \w     32.00  60.00   0.50    0.80    --   47.45-123.00 -37.00   56
 27  \w     31.00  73.00   0.50    3.50    --  103.25 -94.00 -30.00   84
 28  \w     31.00  74.00   0.50    3.50    --  103.25 -61.00 -30.00   86
 29  \w     32.00  73.00   0.50    3.50    --  103.25 -61.00 -60.00   82
 30  \w     31.00  73.00   0.50    3.50    --  103.25 -61.00-180.00   84
 31  \w     32.00  84.00   0.50    3.50    --  103.25 -94.00-180.00  104
 32  \w    -24.00  21.00   0.50    0.80    --   47.45 -19.00 -90.00   90
 33  \w     68.00 108.00   0.50    3.50    --  103.25-106.00  99.37   80
 34  \w     64.00  89.00   0.50    3.50    --  103.25-148.00 159.00   50
 35  \w     46.00  71.00   0.50    0.80    --   47.45-148.00 159.00   50
 36  \w     32.00  57.00   0.50    3.50    --  103.25-106.00  99.37   50
 37  \w     54.00  91.00   0.50    3.50    --  103.25 -94.00 120.00   74
 38  \w   -106.00 -78.00   0.50    0.80    --  -47.45-125.00 -30.00   56
 39  \w   -119.00 -77.00   0.50    0.80    --  -47.45-125.00  30.00   84
 40  \w   -120.00 -26.00   0.50    0.80    --  -47.45 -77.00 -30.00  188
 41  \w   -100.00 -61.00   0.50    0.80    --  -47.45-148.00 159.00   78
 42  \w    -84.00 -59.00   0.50    3.50    --  -99.00-148.00 159.00   50
 43  \w   -146.00-121.00   0.50    3.50    --  -99.00-123.00 -37.00   50
 44  \w   -119.00 -75.00   0.50    0.80    --  -47.45-125.00 -60.00   88
 45  \w   -120.00 -94.00   0.50    3.50    --  -99.00 -30.00-150.00   52
 46  \w   -167.00-142.00   0.50    3.50    --  -99.00 -30.00-150.00   50
 47  \w   -159.00 -81.00   0.50    3.50    --  -99.00 -77.00-180.00  156
 48  \w   -166.00 -87.00   0.50    3.50    --  -99.00 -45.00  30.00  158
 49  \w   -166.00-103.00   0.50    3.50    --  -99.00 -45.00  60.00  126
 50  \w   -123.00 -97.00   0.50    3.50    --  -99.00 141.00  71.86   52
 51  \w   -130.00 -85.00   0.50    3.50    --  -99.00 151.00 115.78   90
 52  \w    -97.00 -34.00   0.50    3.50    --  -99.00 148.00-153.00  126
 53  \w   -126.00 -99.00   0.50    3.50    --  -99.00 148.00-153.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0162102000
_diffrn_orient_matrix_UB_12      0.0262425000
_diffrn_orient_matrix_UB_13      -0.0510730000
_diffrn_orient_matrix_UB_21      -0.0993910000
_diffrn_orient_matrix_UB_22      -0.0496188000
_diffrn_orient_matrix_UB_23      -0.0025531000
_diffrn_orient_matrix_UB_31      -0.0911301000
_diffrn_orient_matrix_UB_32      0.0681776000
_diffrn_orient_matrix_UB_33      0.0043967000
_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     0.1100
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            24330
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.449
_diffrn_reflns_theta_min         2.533
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense bronze'
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       plate
_exptl_crystal_F_000             2316
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.103
_refine_diff_density_min         -1.048
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.536
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1492
_refine_ls_number_reflns         24330
_refine_ls_number_restraints     177
_refine_ls_restrained_S_all      1.534
_refine_ls_R_factor_all          0.2019
_refine_ls_R_factor_gt           0.1631
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4168
_refine_ls_wR_factor_ref         0.4440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15159
_reflns_number_total             24330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00658a2.cif
_cod_data_source_block           tx9311_tw_sq
_cod_depositor_comments
'Adding full bibliography for 1568662--1568666.cif.'
_cod_database_code               1568662
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CH
_chemical_oxdiff_usercomment     CH
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7903
 0.2097
2. Restrained distances
 C70B-C69A = C70A-C69A = C72B-C69A = C72A-C69A = C71B-C69A = C71A-C69A
 1.54 with sigma of 0.01
 C77-C69 = C76-C69 = C69-C2
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C69A \\sim C70A \\sim C71A \\sim C72A \\sim C71B \\sim C70B \\sim C72B: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C70 \\sim C71 \\sim C77 \\sim C72 \\sim C2 \\sim C76: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04 within 1.7A
Uanis(C70A) \\sim Ueq, Uanis(C71A) \\sim Ueq, Uanis(C72A) \\sim Ueq,
Uanis(C71B) \\sim Ueq, Uanis(C70B) \\sim Ueq, Uanis(C72B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C70) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C76)
\\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C71) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(C71B)=Sof(H71G)=Sof(H71H)=Sof(H71I)=Sof(C70B)=Sof(H70G)=Sof(H70H)=
 Sof(H70I)=Sof(C72B)=Sof(H72G)=Sof(H72H)=Sof(H72I)=1-FVAR(1)
 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(1)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C76)=Sof(H76A)=Sof(H76B)=Sof(H76C)=
 Sof(C77)=Sof(H77A)=Sof(H77B)=Sof(H77C)=1-FVAR(2)
 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(2)
5.a Ternary CH refined with riding coordinates:
 C73(H73), C74(H74), C75(H75)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C34(H34), C35(H35), C37(H37), C38(H38), C44(H44), C45(H45), C47(H47), C48(H48),
  C54(H54), C55(H55), C57(H57), C58(H58), C64(H64), C65(H65), C67(H67),
 C68(H68), C5A(H5A), C6A(H6A), C7A(H7A), C10A(H10A), C11A(H11A), C14A(H14A),
 C15A(H15A), C16A(H16A), C34A(H34A), C35A(H35A), C37A(H37A), C38A(H38A),
 C44A(H44A), C45A(H45A), C47A(H47A), C48A(H48A), C54A(H54A), C55A(H55A),
 C57A(H57A), C58A(H58A), C64A(H64A), C65A(H65A), C67A(H67A), C68A(H68A)
5.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C50(H50A,H50B,
 H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C60(H60A,H60B,H60C), C61(H61A,
 H61B,H61C), C62(H62A,H62B,H62C), C70(H70A,H70B,H70C), C71(H71A,H71B,H71C),
 C72(H72A,H72B,H72C), C40A(H40D,H40E,H40F), C41A(H41D,H41E,H41F), C42A(H42D,
 H42E,H42F), C50A(H50D,H50E,H50F), C51A(H51D,H51E,H51F), C52A(H52D,H52E,H52F),
 C60A(H60D,H60E,H60F), C61A(H61D,H61E,H61F), C62A(H62D,H62E,H62F), C70A(H70D,
 H70E,H70F), C71A(H71D,H71E,H71F), C72A(H72D,H72E,H72F), C71B(H71G,H71H,H71I),
 C70B(H70G,H70H,H70I), C72B(H72G,H72H,H72I), C2(H2A,H2B,H2C), C76(H76A,H76B,
 H76C), C77(H77A,H77B,H77C)
;
_shelx_res_checksum              97052
_shelx_fab_checksum              48763
_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 2.217
_oxdiff_exptl_absorpt_empirical_full_min 0.442