Retro Baeyer‒Villiger Reaction: Electrochemical Reduction of [60]Fullerene-Fused Lactones to [60]Fullerene-Fused Ketones
Niu, Chuang; Zhou, Dian-Bing; Yang, Yong; Yin, Zheng-Chun; Wang, Guan-Wu; Chemical Science  (2019) –; doi:10.1039/C8SC05089A

data_1550485
_publ_section_title
;
 Retro Baeyer--Villiger Reaction: Electrochemical Reduction of
 [60]Fullerene-Fused Lactones to [60]Fullerene-Fused Ketones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05089A
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C67 H3 Cl O'
_chemical_formula_weight         859.14
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-07-16 deposited with the CCDC.
2019-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.188(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1607(11)
_cell_length_b                   9.8856(11)
_cell_length_c                   16.4378(16)
_cell_measurement_reflns_used    1496
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      67.7910
_cell_measurement_theta_min      4.4480
_cell_volume                     1613.9(3)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6097
_diffrn_reflns_point_group_measured_fraction_full 0.695
_diffrn_reflns_point_group_measured_fraction_max 0.673
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.110
_diffrn_reflns_theta_min         4.452
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.25(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         4132
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0714
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1251P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2230
_reflns_Friedel_coverage         0.312
_reflns_Friedel_fraction_full    0.356
_reflns_Friedel_fraction_max     0.342
_reflns_number_gt                3174
_reflns_number_total             4132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc05089a2.cif
_cod_data_source_block           shelxl
_cod_database_code               1550485
_shelx_estimated_absorpt_t_min   0.612
_shelx_estimated_absorpt_t_max   0.746
_shelxl_version_number           2013-4
_shelx_res_checksum              92403