Diastereoselective Electrophilic α-Hydroxyamination of N-tert-Butanesulfinyl Imidates.
Ma, Peng-Ju; Liu, Hui; Lu, Chong-Dao; Xu, Yan-Jun; Organic letters 19 (2017) 670–673; doi:10.1021/acs.orglett.6b03835

data_1556000
_publ_section_title
;
 Diastereoselective Electrophilic \a-Hydroxyamination of
 N-tert-Butanesulfinyl Imidates.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              670
_journal_page_last               673
_journal_paper_doi               10.1021/acs.orglett.6b03835
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H24 N2 O2 S'
_chemical_formula_sum            'C19 H24 N2 O2 S'
_chemical_formula_weight         344.46
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.392(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0611(4)
_cell_length_b                   6.7430(3)
_cell_length_c                   13.0444(5)
_cell_measurement_reflns_used    4189
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.145
_cell_measurement_theta_min      3.198
_cell_volume                     950.25(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8891
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.194
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1309 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.8028.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.0524P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    0.789
_reflns_Friedel_fraction_max     0.761
_reflns_number_gt                3508
_reflns_number_total             3877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03835_si_002.cif
_cod_data_source_block           4
_cod_database_code               1556000
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C15(H15), C13(H13), C5(H5), C14(H14), C11(H11), C12(H12), C9(H9),
 C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              53696
_shelx_hkl_checksum              88605
_olex2_submission_special_instructions 'No special instructions were received'