Highly soluble C2v-symmetrical fullerene derivatives: efficient synthesis, characterization, and electrochemical study
Ma, Yue; Uchiyama, Kouya; Ueno, Hiroshi; Okada, Hiroshi; Moriyama, Hiroshi; Matsuo, Yutaka; Organic Chemistry Frontiers 6 (2019) 1372–; doi:10.1039/C9QO00056A

data_1554725
_publ_section_title
;
 Highly soluble C2v-symmetrical fullerene derivatives: efficient
 synthesis, characterization, and electrochemical study
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1372
_journal_paper_doi               10.1039/C9QO00056A
_journal_volume                  6
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C76 H32 F8 O8'
_chemical_formula_sum            'C76 H32 F8 O8'
_chemical_formula_weight         1225.02
_chemical_name_systematic
;
 C60(OCH2CH2F)8
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-12-15T16:08:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-12-15 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.518(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.035(12)
_cell_length_b                   15.426(7)
_cell_length_c                   17.593(10)
_cell_measurement_reflns_used    7644
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      3.091
_cell_measurement_wavelength     0.71073
_cell_volume                     5098(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.2085
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5754
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2496
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0016(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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0915
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0162P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1721
_reflns_number_gt                3565
_reflns_number_total             5754
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c9qo00056a2.cif
_cod_data_source_block           octaF8
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1554725