Regioselective Synthesis of 1,4-Di(organo)[60]fullerenes through DMF-assisted Monoaddition of Silylmethyl Grignard Reagents and Subsequent Alkylation Reaction
Yutaka Matsuo; Akihiko Iwashita; Yoko Abe; Chang-Zhi Li; Keiko Matsuo; Masahiko Hashiguchi; Eiichi Nakamura; Journal of the American Chemical Society 130 (2008) 15429–15436; doi:10.1021/ja8041299

data_4108661
_publ_contact_author             'MATSUO, Yutaka'
_publ_contact_author_email       matsuo@chem.s.u-tokyo.ac.jp
_publ_section_title
;
 Regioselective Synthesis of 1,4-Di(organo)[60]fullerenes through
 DMF-assisted Monoaddition of Silylmethyl Grignard Reagents and Subsequent
 Alkylation Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15429
_journal_page_last               15436
_journal_paper_doi               10.1021/ja8041299
_journal_volume                  130
_journal_year                    2008
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C78 H26 Si2'
_chemical_formula_sum            'C78 H26 Si2'
_chemical_formula_weight         1019.17
_chemical_name_systematic
;
 C60CH2SiMe2Ph2
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-08-21T13:30:52-00:00
_cell_angle_alpha                90
_cell_angle_beta                 97.1370(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3602(2)
_cell_length_b                   19.0203(4)
_cell_length_c                   22.6650(4)
_cell_measurement_reflns_used    25393
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3
_cell_measurement_wavelength     1.54178
_cell_volume                     4431.63(15)
_computing_cell_refinement       'CrystalClear (RIGAKU)'
_computing_data_collection       'CrystalClear (RIGAKU)'
_computing_data_reduction        'CrystalClear (RIGAKU)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Imaging Plate'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54173
_diffrn_reflns_av_R_equivalents  0.1095
_diffrn_reflns_av_unetI/netI     0.0996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            50392
_diffrn_reflns_theta_full        68.2
_diffrn_reflns_theta_max         68.2
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        NA
_diffrn_standards_interval_count NA
_diffrn_standards_number         NA
_exptl_absorpt_coefficient_mu    1.171
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       prism
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.45
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0032(8)
_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   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     770
_refine_ls_number_reflns         8033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.168
_refine_ls_R_factor_gt           0.0989
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1578P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2388
_refine_ls_wR_factor_ref         0.3024
_reflns_number_gt                3503
_reflns_number_total             8033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8041299_si_004.cif
_cod_data_source_block           SIMEFPhPh
_cod_database_code               4108661