Synthesis of C<sub>70</sub>-fragment buckybowls bearing alkoxy substituents.
Yakiyama, Yumi; Hishikawa, Shota; Sakurai, Hidehiro; Beilstein journal of organic chemistry 16 (2020) 681–690; doi:10.3762/bjoc.16.66

data_4038257
_publ_section_title
;
 Synthesis of C<sub>70</sub>-fragment buckybowls bearing alkoxy
 substituents.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              681
_journal_page_last               690
_journal_paper_doi               10.3762/bjoc.16.66
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C30 H18 O2'
_chemical_formula_sum            'C30 H18 O2'
_chemical_formula_weight         410.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.382(4)
_cell_length_b                   7.2895(15)
_cell_length_c                   28.978(6)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      15.71
_cell_measurement_theta_min      3.65
_cell_volume                     3671.7(14)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS VII area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3207
_diffrn_reflns_av_unetI/netI     0.4003
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            23687
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.046
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     331
_refine_ls_restrained_S_all      0.885
_refine_ls_R_factor_all          0.4240
_refine_ls_R_factor_gt           0.1319
_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^)+(0.1531P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2925
_refine_ls_wR_factor_ref         0.4008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                925
_reflns_number_total             4205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Dimethoxy-5a-re.cif
_cod_data_source_block           Dimethoxy5a
_cod_depositor_comments
'Adding full bibliography for 4038256--4038257.cif.'
_cod_original_cell_volume        3671.8(13)
_cod_database_code               4038257
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17,
 C18, C19, C20, C21, C22, C23, C24, H24, C25, C26, C27, H27, C28, H30A, H30B,
 H30C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C11, C12, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, C29
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23, C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim H24
\\sim C25 \\sim C26 \\sim C27 \\sim H27 \\sim C28: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
C11 \\sim C12 \\sim C13: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
O1 \\sim C29: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C24, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C16(H16A,H16B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C13(H13), C14(H14), C18(H18), C22(H22), C24(H24), C27(H27)
5.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'