Convergent synthesis of a polyfunctionalized fullerene by regioselective five-fold addition of a functionalized organocopper reagent to C60.
Zhong, Yu-Wu; Matsuo, Yutaka; Nakamura, Eiichi; Organic letters 8 (2006) 1463–1466; doi:10.1021/ol060282t

data_1505912
_publ_section_title
;
 Convergent synthesis of a polyfunctionalized fullerene by regioselective
 five-fold addition of a functionalized organocopper reagent to C60.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1463
_journal_page_last               1466
_journal_paper_doi               10.1021/ol060282t
_journal_volume                  8
_journal_year                    2006
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C113 H56 O10'
_chemical_formula_sum            'C113 H56 O10'
_chemical_formula_weight         1573.58
_chemical_name_systematic
;
 C60C6H4COOEt5Me
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-03-01T21:25:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                76.19
_cell_angle_beta                 75.68
_cell_angle_gamma                70.01
_cell_formula_units_Z            2
_cell_length_a                   14.443
_cell_length_b                   16.347
_cell_length_c                   17.597
_cell_measurement_reflns_used    29714
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      2.42
_cell_measurement_wavelength     0.71073
_cell_volume                     3728.425
_computing_cell_refinement       Scalepack(HKL)
_computing_data_collection       Xpress(MacScience)
_computing_data_reduction        'Denzo and Scalepack(HKL)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Imaging Plate'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13079
_diffrn_reflns_theta_full        25.74
_diffrn_reflns_theta_max         25.74
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        NA
_diffrn_standards_interval_count NA
_diffrn_standards_number         NA
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1628
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.582
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.063(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.476
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1074
_refine_ls_number_reflns         13079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.476
_refine_ls_R_factor_all          0.1852
_refine_ls_R_factor_gt           0.1439
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3778
_refine_ls_wR_factor_ref         0.4211
_reflns_number_gt                7917
_reflns_number_total             13079
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060282tsi20060301_080453.cif
_cod_data_source_block           import
_cod_original_cell_volume        3728.5
_cod_database_code               1505912