Catalytic Asymmetric Oxidative α-C-H N,O-Ketalization of Ketones by Chiral Primary Amine.
Xu, Changming; Zhang, Long; Luo, Sanzhong; Organic letters 17 (2015) 4392–4395; doi:10.1021/acs.orglett.5b02322

data_1555296
_publ_section_title
;
 Catalytic Asymmetric Oxidative \a-C-H N,O-Ketalization of Ketones by
 Chiral Primary Amine.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4392
_journal_page_last               4395
_journal_paper_doi               10.1021/acs.orglett.5b02322
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C21 H22 N2 O6 S'
_chemical_formula_sum            'C21 H22 N2 O6 S'
_chemical_formula_weight         430.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                65.028(8)
_cell_angle_beta                 72.368(11)
_cell_angle_gamma                76.052(11)
_cell_formula_units_Z            2
_cell_length_a                   10.449(2)
_cell_length_b                   10.564(2)
_cell_length_c                   10.913(2)
_cell_measurement_reflns_used    3418
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4827
_cell_measurement_theta_min      2.5950
_cell_volume                     1031.7(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0941
_diffrn_orient_matrix_UB_12      0.0347
_diffrn_orient_matrix_UB_13      -0.0142
_diffrn_orient_matrix_UB_21      0.0238
_diffrn_orient_matrix_UB_22      -0.1024
_diffrn_orient_matrix_UB_23      0.0062
_diffrn_orient_matrix_UB_31      -0.0478
_diffrn_orient_matrix_UB_32      0.0238
_diffrn_orient_matrix_UB_33      -0.0891
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13003
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.598
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0349P)^2^+0.3791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4385
_reflns_number_total             4711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02322_si_002.cif
_cod_data_source_block           sa3715
_cod_original_cell_volume        1031.8(4)
_cod_database_code               1555296
_shelxl_version_number           2013-4
_diffrn_number_total             4717
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
;
_shelx_res_checksum              5645
_shelx_hkl_checksum              81766