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_7109850
_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         'C18 H21 N O2 S'
_chemical_formula_sum            'C18 H21 N O2 S'
_chemical_formula_weight         315.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.5824(3)
_cell_length_b                   15.4160(11)
_cell_length_c                   22.7652(14)
_cell_measurement_reflns_used    5175
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      74.41
_cell_measurement_theta_min      3.46
_cell_volume                     1608.19(18)
_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 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -69.00   22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7877   57.0000  150.0000 91

  2 omega   30.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   57.0000 -180.0000 66

  3 omega -110.00  -83.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000 -125.0000 -180.0000 27

  4 omega   33.00   69.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  -60.0000 36

  5 omega   40.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  -90.0000 26

  6 omega   35.00   68.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000    0.0000 33

  7 omega   43.00   72.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000   90.0000 29

  8 omega   39.00   65.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  -30.0000 26

  9 omega   41.00  103.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000  120.0000 62

 10 omega   79.00  110.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000 -120.0000 31

 11 omega   33.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -120.0000 33

 12 omega   33.00   65.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -150.0000 32

 13 omega  113.00  139.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000  -90.0000 26

 14 omega   46.00  135.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -77.0000  -60.0000 89

 15 omega -115.00  -14.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7877  -77.0000   30.0000 101

 16 omega   19.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   57.0000  -90.0000 93

 17 omega  -25.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877  -57.0000 -120.0000 94

 18 omega   76.00  141.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   77.0000  -90.0000 65

 19 omega   85.00  158.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000   60.0000 73

 20 omega   76.00  158.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   77.0000  -30.0000 82
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.3332502000
_diffrn_orient_matrix_UB_12      0.0130527000
_diffrn_orient_matrix_UB_13      -0.0005400000
_diffrn_orient_matrix_UB_21      0.0014207000
_diffrn_orient_matrix_UB_22      -0.0030675000
_diffrn_orient_matrix_UB_23      -0.0676131000
_diffrn_orient_matrix_UB_31      -0.0444509000
_diffrn_orient_matrix_UB_32      -0.0990598000
_diffrn_orient_matrix_UB_33      0.0021125000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11325
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.585
_diffrn_reflns_theta_min         3.462
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.836
_exptl_absorpt_correction_T_max  1.166
_exptl_absorpt_correction_T_min  0.695
_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    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3567
_exptl_crystal_size_mid          0.0995
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1227 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.004(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0479P)^2^+0.2837P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3123
_reflns_number_total             3213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc45452e.txt
_cod_data_source_block           5b
_cod_original_cell_volume        1608.19(19)
_cod_database_code               7109850
_nottingham_internal_coll_name   ERRSCB
_nottingham_internal_coll_number 11368
_nottingham_internal_coll_client ER/RS
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '12.0000 and 3.0000'
_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 04/04/2012
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 4/4/2013
_nottingham_internal_refinement_user WL
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 20/4/2013
_chemical_oxdiff_formula         'C18 H21 N O2 S'
_chemical_oxdiff_usercomment
'ERRSCB #138 IN FOMBLIN FILM ON MICROMOUNT FOR ER/RS'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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