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_7109849
_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_formula_moiety         'C18 H21 N O S'
_chemical_formula_sum            'C18 H21 N O S'
_chemical_formula_weight         299.42
_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   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                 94.048(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.60842(14)
_cell_length_b                   24.0504(8)
_cell_length_c                   14.1862(5)
_cell_measurement_reflns_used    9610
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      77.1999
_cell_measurement_theta_min      3.6210
_cell_volume                     1568.40(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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      90(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -92.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  125.0000   90.0000 90

  2 omega   50.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   38.0000   60.0000 58

  3 omega   64.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   57.0000  -60.0000 25

  4 omega   24.00   87.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   38.0000 -120.0000 63

  5 omega   14.00  101.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   77.0000  -30.0000 87

  6 omega   20.00   55.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   57.0000  -60.0000 35

  7 omega   43.00   77.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -30.0000 34

  8 omega   40.00   68.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   30.0000 28

  9 omega   38.00   69.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   60.0000 31

 10 omega   45.00   72.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -120.0000 27

 11 omega   39.00   66.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  150.0000 27

 12 omega   56.00   89.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000  120.0000 33

 13 omega   53.00   80.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -95.0000  -60.0000 27

 14 omega   48.00   75.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -95.0000  150.0000 27

 15 omega   95.00  158.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000 -120.0000 63

 16 omega   38.00   69.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   90.0000 31

 17 omega   55.00   82.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000 -120.0000 27

 18 omega   38.00   63.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -150.0000 25

 19 omega   91.00  116.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000 -120.0000 25

 20 omega   38.00   69.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  120.0000 31

 21 omega   84.00  128.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  -30.0000 44

 22 omega   47.00   74.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000  -60.0000 27

 23 omega  104.00  131.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000  -60.0000 27

 24 omega   29.00  149.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000    0.0000   60.0000 120

 25 omega   96.00  125.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000 -150.0000 29

 26 omega   91.00  156.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000  -90.0000 65

 27 omega   75.00  102.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -95.0000 -180.0000 27

 28 omega   76.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -95.0000  -90.0000 27

 29 omega   34.00   74.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -95.0000  -30.0000 40

 30 omega   45.00   71.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -95.0000 -180.0000 26

 31 omega   38.00   63.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -180.0000 25

 32 omega   43.00  112.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000   90.0000 69

 33 omega   47.00  115.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000  150.0000 68

 34 omega   48.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -95.0000    0.0000 61

 35 omega   60.00  136.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000  150.0000 76

 36 omega  -69.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   57.0000   90.0000 93

 37 omega -115.00  -14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  -77.0000   90.0000 101

 38 omega  -69.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   57.0000    0.0000 93

 39 omega -115.00  -14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  -77.0000    0.0000 101

 40 omega   62.00  111.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127  145.0000  -16.0000 49

 41 omega   19.00  112.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   57.0000 -120.0000 93

 42 omega   23.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   38.0000  150.0000 92

 43 omega   90.00  158.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000  150.0000 68
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0599307000
_diffrn_orient_matrix_UB_12      0.0470543000
_diffrn_orient_matrix_UB_13      -0.0697596000
_diffrn_orient_matrix_UB_21      -0.0328503000
_diffrn_orient_matrix_UB_22      0.0432477000
_diffrn_orient_matrix_UB_23      0.0786808000
_diffrn_orient_matrix_UB_31      0.3279351000
_diffrn_orient_matrix_UB_32      -0.0042475000
_diffrn_orient_matrix_UB_33      0.0283853000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20574
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.411
_diffrn_reflns_theta_min         3.624
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_T_max  1.093
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2895
_exptl_crystal_size_mid          0.0949
_exptl_crystal_size_min          0.0361
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0452P)^2^+0.8020P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3110
_reflns_number_total             3291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc45452e.txt
_cod_data_source_block           2c
_cod_database_code               7109849
_nottingham_internal_coll_name   ERRSCC
_nottingham_internal_coll_number 11369
_nottingham_internal_coll_client ER/RS
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '10.0000 and 40.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   3/4/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 05/04/2012
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 5/4/2012
_nottingham_internal_refinement_user WL
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 20/5/2013
_chemical_oxdiff_formula         'C18 H21 N O S'
_chemical_oxdiff_usercomment
'ERRSCC #11369 IN FOMBLIN FILM ON MICROMOUNT FOR ER/RS'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.91 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1A)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelxl_version_number           2013-2