N-Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β-Hydroxylation of Enals.
Zhang, Yuexia; Du, Yu; Huang, Zhijian; Xu, Jianfeng; Wu, Xingxing; Wang, Yuhuang; Wang, Ming; Yang, Song; Webster, Richard D.; Chi, Yonggui Robin; Journal of the American Chemical Society 137 (2015) 2416–2419; doi:10.1021/ja511371a

data_4123420
_publ_section_title
;
 N-Heterocyclic Carbene-Catalyzed Radical Reactions for Highly
 Enantioselective \b-Hydroxylation of Enals.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2416
_journal_page_last               2419
_journal_paper_doi               10.1021/ja511371a
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C6 H4 K N O5 S'
_chemical_formula_weight         241.26
_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
_cell_angle_alpha                90
_cell_angle_beta                 100.100(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.097(2)
_cell_length_b                   7.8518(14)
_cell_length_c                   7.2255(12)
_cell_measurement_reflns_used    1989
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      25.1611
_cell_measurement_theta_min      3.8652
_cell_volume                     843.2(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18680
_diffrn_reflns_theta_full        31.09
_diffrn_reflns_theta_max         31.09
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.530
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0317P)^2^+0.2175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0887
_reflns_number_gt                1864
_reflns_number_total             2709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511371a_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 4123420.cif.'
_cod_database_code               4123420
_shelx_res_checksum              79077
_shelx_hkl_checksum              9341