Highly diastereoselective radical cyclisations of chiral sulfinimines
Elise M. Rochette; William Lewis; Al G. Dossetter; Robert A. Stockman; Chem.Commun. 49 (2013) 9395–; doi:10.1039/c3cc45452e

data_7109852
_publ_section_title
;
 Highly diastereoselective radical cyclisations of chiral sulfinimines
;
_journal_name_full               Chem.Commun.
_journal_page_first              9395
_journal_paper_doi               10.1039/c3cc45452e
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 N O S2'
_chemical_formula_sum            'C16 H19 N O S2'
_chemical_formula_weight         305.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-20
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.954(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1360(9)
_cell_length_b                   4.5783(3)
_cell_length_c                   23.0086(13)
_cell_measurement_reflns_used    5974
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      77.6780
_cell_measurement_theta_min      2.8140
_cell_volume                     1553.85(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.6296
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9855
_diffrn_measurement_details
;
  1 omega  -78.00  -11.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6804  125.0000 -180.0000 67

  2 omega   18.00   92.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804 -125.0000   90.0000 74

  3 omega  -31.00   45.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804  -57.0000  -60.0000 76

  4 omega   14.00   88.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804   57.0000 -180.0000 74

  5 omega   27.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804   38.0000   90.0000 82

  6 omega  118.00  145.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -15.0000 -180.0000 27

  7 omega   61.00  137.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -77.0000  -30.0000 76

  8 omega   34.00   92.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -15.0000 -180.0000 58

  9 omega   73.00  108.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -94.0000   60.0000 35

 10 omega   89.00  132.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -77.0000 -150.0000 43

 11 omega   45.00   87.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -15.0000  -30.0000 42

 12 omega   90.00  130.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   30.0000 -180.0000 40

 13 omega  136.00  163.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   30.0000 -180.0000 27

 14 omega   67.00   97.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -45.0000 -180.0000 30

 15 omega   45.00   83.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -77.0000 -150.0000 38

 16 omega  105.00  138.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   15.0000  150.0000 33

 17 omega   38.00   91.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -30.0000  -60.0000 53

 18 omega   89.00  138.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -77.0000   90.0000 49

 19 omega   60.00   87.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -77.0000   90.0000 27

 20 omega   78.00  107.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -94.0000 -150.0000 29

 21 omega   47.00   98.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -45.0000    0.0000 51

 22 omega   40.00   82.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -45.0000 -120.0000 42

 23 omega   86.00  172.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   77.0000    0.0000 86

 24 omega   91.00  127.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -15.0000  -30.0000 36

 25 omega   74.00  111.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   15.0000  120.0000 37

 26 omega  130.00  157.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   15.0000  120.0000 27

 27 omega   98.00  135.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   45.0000 -120.0000 37

 28 omega   91.00  127.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000 -150.0000   66.0000 36

 29 omega   85.00  135.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -61.0000 -150.0000 50

 30 omega   45.00   72.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -61.0000  -60.0000 27

 31 omega   87.00  114.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -61.0000  -60.0000 27

 32 omega   32.00   96.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -15.0000 -120.0000 64

 33 omega   78.00  177.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   15.0000 -120.0000 99

 34 omega    8.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804   77.0000 -150.0000 101

 35 omega  -33.00   58.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804  -38.0000  120.0000 91

 36 omega   13.00  106.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804   57.0000  -30.0000 93

 37 omega  -33.00   58.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804  -38.0000   30.0000 91

 38 omega  -33.00   58.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804  -38.0000  -60.0000 91

 39 omega    8.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804   77.0000  -30.0000 101

 40 omega    8.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6804   77.0000   60.0000 101

 41 omega   84.00  178.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   61.0000   90.0000 94

 42 omega   37.00   91.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -30.0000   60.0000 54

 43 omega   88.00  153.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   45.0000    0.0000 65

 44 omega   89.00  178.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   30.0000  -30.0000 89
;
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0522689000
_diffrn_orient_matrix_UB_12      0.2891967000
_diffrn_orient_matrix_UB_13      0.0009766000
_diffrn_orient_matrix_UB_21      0.0146744000
_diffrn_orient_matrix_UB_22      0.0114224000
_diffrn_orient_matrix_UB_23      0.0684394000
_diffrn_orient_matrix_UB_31      0.0892299000
_diffrn_orient_matrix_UB_32      -0.1713530000
_diffrn_orient_matrix_UB_33      0.0062272000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10794
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.547
_diffrn_reflns_theta_min         3.943
_diffrn_source                   'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.055
_exptl_absorpt_correction_T_max  1.339
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.5878
_exptl_crystal_size_mid          0.0928
_exptl_crystal_size_min          0.0152
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.013(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3267
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0616P)^2^+3.9242P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3094
_reflns_number_total             3267
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc45452e.txt
_cod_data_source_block           10b
_cod_original_cell_volume        1553.86(16)
_cod_database_code               7109852
_nottingham_internal_coll_name   ERRSCE
_nottingham_internal_coll_number 11660
_nottingham_internal_coll_client AJ/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '20.0000 and 80.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   12/7/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 17/07/2012
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 12/7/2012
_nottingham_internal_refinement_user WL
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 20/5/2013
_chemical_oxdiff_formula         'C16 H19 N O2 S'
_chemical_oxdiff_usercomment
'ERRSCE #12381 IN FOMBLIN FILM ON MICROMOUNT FOR ER/RS'
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1
 0.91 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1A)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C12(H12)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_shelxl_version_number           2013-2