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_1568663
_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 H54, 1.815(C7 H8)'
_chemical_formula_sum            'C84.7 H68.52'
_chemical_formula_weight         1086.34
_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             2022-09-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-09-19 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.5252(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.53234(11)
_cell_length_b                   17.84770(19)
_cell_length_c                   30.0310(3)
_cell_measurement_reflns_used    35107
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      65.653
_cell_measurement_theta_min      3.83
_cell_volume                     6178.96(11)
_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_temperature      170.00(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1257
_diffrn_reflns_av_unetI/netI     0.0911
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            72668
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        63.023
_diffrn_reflns_theta_max         63.023
_diffrn_reflns_theta_min         3.848
_exptl_absorpt_coefficient_mu    0.496
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       needle
_exptl_crystal_F_000             2307
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     918
_refine_ls_number_reflns         9972
_refine_ls_number_restraints     732
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0931P)^2^+0.9974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1590
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8842
_reflns_number_total             9972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00658a2.cif
_cod_data_source_block           zrh2_max_reject
_cod_depositor_comments
'Adding full bibliography for 1568662--1568666.cif.'
_cod_original_formula_sum        'C84.70 H68.52'
_cod_database_code               1568663
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Restrained distances
 C3B'-C2B' = C4B'-C3B' = C5B'-C4B' = C6B'-C5B' = C6B'-C1B' = C2B'-C1B'
 1.39 with sigma of 0.01
 C6B-C1B = C6B-C5B = C5B-C4B = C4B-C3B = C3B-C2B = C2B-C1B
 1.39 with sigma of 0.01
2. Restrained planarity
 C1A', C2A', C3A', C4A', C5A', C6A', C7A'
 with sigma of 0.01
 C1B, C2B, C3B, C4B, C5B, C6B, C7B
 with sigma of 0.01
 C1B', C2B', C3B', C4B', C5B', C6B', C7B'
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A \\sim C1A'
\\sim C2A' \\sim C3A' \\sim C4A' \\sim C5A' \\sim C6A' \\sim C7A': within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B \\sim C6B \\sim C7B \\sim C1B'
\\sim C2B' \\sim C3B' \\sim C4B' \\sim C5B' \\sim C6B' \\sim C7B': within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C1A, C2A, C3A, C4A, C5A, C6A, C7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1A', C2A', C3A', C4A', C5A', C6A', C7A'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B, C2B, C3B, C4B, C5B, C6B, C7B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B', C2B', C3B', C4B', C5B', C6B', C7B'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C1A', C2A', C3A', C4A', C5A', C6A', C7A'} sigma for 1-2: 0.01, 1-3: 0.04
{C1B, C2B, C3B, C4B, C5B, C6B, C7B} sigma for 1-2: 0.01, 1-3: 0.04
{C1B', C2B', C3B', C4B', C5B', C6B', C7B'} sigma for 1-2: 0.01, 1-3: 0.04
as in
{C1A, C2A, C3A, C4A, C5A, C6A, C7A}
6. Others
 Sof(C1A')=Sof(C2A')=Sof(H2A')=Sof(C3A')=Sof(H3A')=Sof(C4A')=Sof(H4A')=
 Sof(C5A')=Sof(H5A')=Sof(C6A')=Sof(H6A')=Sof(C7A')=Sof(H7AD)=Sof(H7AE)=
 Sof(H7AF)=1-FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=
 Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=FVAR(1)
 Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=
 Sof(H5B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7BA)=Sof(H7BB)=Sof(H7BC)=FVAR(2)
 Sof(C1B')=Sof(C2B')=Sof(H2B')=Sof(C3B')=Sof(H3B')=Sof(C4B')=Sof(H4B')=
 Sof(C5B')=Sof(H5B')=Sof(C6B')=Sof(H6B')=Sof(C7B')=Sof(H7BD)=Sof(H7BE)=
 Sof(H7BF)=FVAR(3)
7.a Me refined with riding coordinates:
 C7A'(H7AD,H7AE,H7AF), C7B'(H7BD,H7BE,H7BF)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C23(H23), C24(H24), C30(H30), C31(H31), C32(H32), C37(H37), C38(H38), C40(H40),
  C43(H43), C45(H45), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A),
 C2A'(H2A'), C3A'(H3A'), C4A'(H4A'), C5A'(H5A'), C6A'(H6A'), C2B(H2B), C3B(H3B),
  C4B(H4B), C5B(H5B), C6B(H6B), C2B'(H2B'), C3B'(H3B'), C4B'(H4B'), C5B'(H5B'),
 C6B'(H6B')
7.c Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C62(H62A,H62B,
 H62C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C67(H67A,
 H67B,H67C), C68(H68A,H68B,H68C), C70(H70A,H70B,H70C), C71(H71A,H71B,H71C),
 C72(H72A,H72B,H72C), C7A(H7AA,H7AB,H7AC), C7B(H7BA,H7BB,H7BC)
;
_shelx_res_checksum              72241
_olex2_submission_special_instructions 'No special instructions were received'