Synthesis of C5-symmetric functionalized [60]fullerenes by copper-mediated 5-fold addition of Reformatsky reagents.
Nakae, Takahiro; Matsuo, Yutaka; Nakamura, Eiichi; Organic letters 10 (2008) 621–623; doi:10.1021/ol702874w

data_1504521
_publ_contact_author             'MATSUO, Yutaka'
_publ_section_title
;
 Synthesis of C5-symmetric functionalized [60]fullerenes by
 copper-mediated 5-fold addition of Reformatsky reagents.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              621
_journal_page_last               623
_journal_paper_doi               10.1021/ol702874w
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C85 H40 Fe1 O10'
_chemical_formula_sum            'C85 H40 Fe O10'
_chemical_formula_weight         1277.02
_chemical_name_systematic
;
 FeC60CH2COOEt5Cp
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2005-10-31T16:18:29-00:00
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0920(5)
_cell_length_b                   14.4240(14)
_cell_length_c                   27.580(2)
_cell_measurement_reflns_used    36965
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.22
_cell_measurement_wavelength     0.71073
_cell_volume                     5208.2(7)
_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    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_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     0.0375
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5299
_diffrn_reflns_theta_full        25.72
_diffrn_reflns_theta_max         25.72
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.37
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.183
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.29(4)
_refine_ls_extinction_coef       0.039(3)
_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   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     866
_refine_ls_number_reflns         5299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0856
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1565P)^2^+5.1452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2101
_refine_ls_wR_factor_ref         0.2325
_reflns_number_gt                4499
_reflns_number_total             5299
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702874w-file001.cif
_cod_data_source_block           FeCH2es
_cod_database_code               1504521