Asymmetric Baeyer-Villiger oxidation: classical and parallel kinetic resolution of 3-substituted cyclohexanones and desymmetrization of meso-disubstituted cycloketones
Wu, Wangbin; Cao, Weidi; Hu, Linfeng; Su, Zhishan; Liu, Xiaohua; Feng, Xiaoming; Chemical Science  (2019) –; doi:10.1039/C9SC01563A

data_1551307
_publ_section_title
;
 Asymmetric Baeyer-Villiger oxidation: classical and parallel kinetic
 resolution of 3-substituted cyclohexanones and desymmetrization of
 meso-disubstituted cycloketones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01563A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C54 H77 F9 N4 O13 S3 Sc'
_chemical_formula_weight         1302.33
_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-2016/6
_audit_update_record
;
2018-07-18 deposited with the CCDC.    2019-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.46(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.205(14)
_cell_length_b                   27.45(2)
_cell_length_c                   11.970(16)
_cell_measurement_reflns_used    8159
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.48
_cell_volume                     3261(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            53451
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         2.294
_exptl_absorpt_coefficient_mu    0.294
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             1366
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.521
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 2994 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     770
_refine_ls_number_reflns         16015
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1552
_refine_ls_R_factor_gt           0.0971
_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^)+(0.1592P)^2^+2.2065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2454
_refine_ls_wR_factor_ref         0.2957
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                9635
_reflns_number_total             16015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01563a2.cif
_cod_data_source_block           mo_20180704_WWB_01_0m_a
_cod_database_code               1551307
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.933
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              55995