Diversion of the Arbuzov reaction: alkylation of C-Cl instead of phosphonic ester formation on the fullerene cage.
Kraevaya, Ol'ga A.; Peregudov, Alexander S.; Troyanov, Sergey I.; Godovikov, Ivan; Fedorova, Natalya E.; Klimova, Regina R.; Sergeeva, Vasilina A.; Kameneva, Larisa V.; Ershova, Elizaveta S.; Martynenko, Vyacheslav M.; Claes, Sandra; Kushch, Alla A.; Kostyuk, Svetlana V.; Schols, Dominique; Shestakov, Alexander F.; Troshin, Pavel A.; Organic & biomolecular chemistry 17 (2019) 7155–7160; doi:10.1039/c9ob00593e

data_7156869
_publ_section_title
;
 Diversion of the Arbuzov reaction: alkylation of C-Cl instead of
 phosphonic ester formation on the fullerene cage.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7155
_journal_page_last               7160
_journal_paper_doi               10.1039/c9ob00593e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C100 H35 O20'
_chemical_formula_weight         1556.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-01-24 deposited with the CCDC.    2019-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_measurement_temperature    100(2)
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_cell_volume                     7193.7(9)
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_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXD
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.800
_diffrn_measurement_device_type  MAR225
_diffrn_measurement_method       CCD
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.895
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.915
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_diffrn_reflns_limit_k_min       -19
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_diffrn_reflns_number            85973
_diffrn_reflns_point_group_measured_fraction_full 0.915
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_diffrn_reflns_theta_max         36.172
_diffrn_reflns_theta_min         2.027
_diffrn_source                   'BL 14.3 PSF, BESSY, Berlin, Germany'
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       plate
_exptl_crystal_F_000             3180
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.015
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_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         13833
_refine_ls_number_restraints     278
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.2316
_refine_ls_R_factor_gt           0.1818
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3751
_refine_ls_wR_factor_ref         0.3908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7916
_reflns_number_total             13833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00593e2.cif
_cod_data_source_block           232
_cod_depositor_comments          'Adding full bibliography for 7156869.cif.'
_cod_database_code               7156869
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.995
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              47460