General One-step Synthesis of Symmetrical or Unsymmetrical 1,4-Di(organo)fullerenes from Organo(hydro)fullerenes through Direct Oxidative Arylation.
Wu, Yin-Fu; Wang, Shan-Shan; Yao, Chun-Rui; Chen, Zuo-Chang; Li, Shu-Hui; Yao, Yang-Rong; Zhang, Xue-Peng; Su, Yin; Deng, Shun-Liu; Zhang, Qianyan; Gao, Fei; Xie, Su-Yuan; Huang, Rong-Bin; Zheng, Lan-Sun; The Journal of organic chemistry 84 (2019) 12259–12267; doi:10.1021/acs.joc.9b01272

data_4033987
_publ_section_title
;
 General One-step Synthesis of Symmetrical or Unsymmetrical
 1,4-Di(organo)fullerenes from Organo(hydro)fullerenes through Direct
 Oxidative Arylation.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12259
_journal_page_last               12267
_journal_paper_doi               10.1021/acs.joc.9b01272
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C75 H14 O3'
_chemical_formula_sum            'C75 H14 O3'
_chemical_formula_weight         962.86
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7603(3)
_cell_length_b                   16.2554(2)
_cell_length_c                   27.9643(5)
_cell_measurement_reflns_used    7141
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      61.4850
_cell_measurement_theta_min      4.1060
_cell_volume                     7618.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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     46.00  73.00   1.00    4.00    --    0.00  37.00-120.00   27
  2  \w    -88.00 -62.00   1.00    4.00    --    0.00 178.00 -30.00   26
  3  \w     24.00  77.00   1.00    4.00    --    0.00  77.00 -30.00   53
  4  \w    -27.00   0.00   1.00    4.00    --    0.00  77.00 -30.00   27
  5  \w    -87.00 -44.00   1.00    4.00    --    0.00-178.00 -60.00   43
  6  \w    -25.00  14.00   1.00    4.00    --    0.00  37.00-120.00   39
  7  \w      7.00  89.00   1.00   20.00    --   82.47 -30.00 -30.00   82
  8  \w     56.00  90.00   1.00   20.00    --   82.47 -30.00-180.00   34
  9  \w     26.00 120.00   1.00   20.00    --   82.47-125.00-180.00   94
 10  \w     27.00 111.00   1.00   20.00    --   82.47 -77.00-150.00   84
 11  \w      5.00  31.00   1.00   20.00    --   82.47 -30.00-180.00   26
 12  \w     55.00 157.00   1.00   20.00    --   82.47  61.00 -30.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0507943000
_diffrn_orient_matrix_UB_12      0.0192810000
_diffrn_orient_matrix_UB_13      -0.0445084000
_diffrn_orient_matrix_UB_21      0.0757882000
_diffrn_orient_matrix_UB_22      0.0007238000
_diffrn_orient_matrix_UB_23      0.0311641000
_diffrn_orient_matrix_UB_31      0.0111797000
_diffrn_orient_matrix_UB_32      -0.0928046000
_diffrn_orient_matrix_UB_33      -0.0090356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23895
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        61.419
_diffrn_reflns_theta_max         61.419
_diffrn_reflns_theta_min         4.105
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       block
_exptl_crystal_F_000             3904
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1246
_refine_ls_number_reflns         5842
_refine_ls_number_restraints     1080
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0698
_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^)+(0.1270P)^2^+0.5292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4453
_reflns_number_total             5842
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01272_si_003.cif
_cod_data_source_block           exp_5033-1
_cod_database_code               4033987
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C75O2
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.910
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     57.83
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A \\sim C8A \\sim
C9A \\sim C10A \\sim C11A \\sim C12A \\sim C13A \\sim C14A \\sim C15A \\sim
C16A \\sim C17A \\sim C18A \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim
C23A \\sim C24A \\sim C25A \\sim C26A \\sim C27A \\sim C28A \\sim C29A \\sim
C30A \\sim C31A \\sim C32A \\sim C33A \\sim C34A \\sim C35A \\sim C36A \\sim
C37A \\sim C38A \\sim C39A \\sim C40A \\sim C41A \\sim C42A \\sim C43A \\sim
C44A \\sim C45A \\sim C46A \\sim C47A \\sim C48A \\sim C49A \\sim C50A \\sim
C51A \\sim C52A \\sim C53A \\sim C54A \\sim C55A \\sim C56A \\sim C57A \\sim
C58A \\sim C59A \\sim C60A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B \\sim C6B \\sim C7B \\sim C8B \\sim
C9B \\sim C10B \\sim C11B \\sim C12B \\sim C13B \\sim C14B \\sim C15B \\sim
C16B \\sim C17B \\sim C18B \\sim C19B \\sim C20B \\sim C21B \\sim C22B \\sim
C23B \\sim C24B \\sim C25B \\sim C26B \\sim C27B \\sim C28B \\sim C29B \\sim
C30B \\sim C31B \\sim C32B \\sim C33B \\sim C34B \\sim C35B \\sim C36B \\sim
C37B \\sim C38B \\sim C39B \\sim C40B \\sim C41B \\sim C42B \\sim C43B \\sim
C44B \\sim C45B \\sim C46B \\sim C47B \\sim C48B \\sim C49B \\sim C50B \\sim
C51B \\sim C52B \\sim C53B \\sim C54B \\sim C55B \\sim C56B \\sim C57B \\sim
C58B \\sim C59B \\sim C60B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Others
 Sof(C1B)=Sof(C2B)=Sof(C3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=Sof(C7B)=Sof(C8B)=
 Sof(C9B)=Sof(C10B)=Sof(C11B)=Sof(C12B)=Sof(C13B)=Sof(C14B)=Sof(C15B)=Sof(C16B)=
 Sof(C17B)=Sof(C18B)=Sof(C19B)=Sof(C20B)=Sof(C21B)=Sof(C22B)=Sof(C23B)=
 Sof(C24B)=Sof(C25B)=Sof(C26B)=Sof(C27B)=Sof(C28B)=Sof(C29B)=Sof(C30B)=
 Sof(C31B)=Sof(C32B)=Sof(C33B)=Sof(C34B)=Sof(C35B)=Sof(C36B)=Sof(C37B)=
 Sof(C38B)=Sof(C39B)=Sof(C40B)=Sof(C41B)=Sof(C42B)=Sof(C43B)=Sof(C44B)=
 Sof(C45B)=Sof(C46B)=Sof(C47B)=Sof(C48B)=Sof(C49B)=Sof(C50B)=Sof(C51B)=
 Sof(C52B)=Sof(C53B)=Sof(C54B)=Sof(C55B)=Sof(C56B)=Sof(C57B)=Sof(C58B)=
 Sof(C59B)=Sof(C60B)=1-FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=Sof(C7A)=Sof(C8A)=
 Sof(C9A)=Sof(C10A)=Sof(C11A)=Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(C15A)=Sof(C16A)=
 Sof(C17A)=Sof(C18A)=Sof(C19A)=Sof(C20A)=Sof(C21A)=Sof(C22A)=Sof(C23A)=
 Sof(C24A)=Sof(C25A)=Sof(C26A)=Sof(C27A)=Sof(C28A)=Sof(C29A)=Sof(C30A)=
 Sof(C31A)=Sof(C32A)=Sof(C33A)=Sof(C34A)=Sof(C35A)=Sof(C36A)=Sof(C37A)=
 Sof(C38A)=Sof(C39A)=Sof(C40A)=Sof(C41A)=Sof(C42A)=Sof(C43A)=Sof(C44A)=
 Sof(C45A)=Sof(C46A)=Sof(C47A)=Sof(C48A)=Sof(C49A)=Sof(C50A)=Sof(C51A)=
 Sof(C52A)=Sof(C53A)=Sof(C54A)=Sof(C55A)=Sof(C56A)=Sof(C57A)=Sof(C58A)=
 Sof(C59A)=Sof(C60A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C62(H62), C63(H63), C66(H66), C71(H71), C72(H72), C73(H73), C74(H74), C75(H75)
4.b Idealised Me refined as rotating group:
 C67(H67A,H67B,H67C), C69(H69A,H69B,H69C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.647