The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines
Pham, Quoc Hoang; Tague, Andrew James; Richardson, Christopher; Hyland, Christopher James Timothy; Pyne, Stephen G.; Chemical Science  (2021) –; doi:10.1039/D1SC03268B

data_1564388
_publ_section_title
;
 The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate
 imines
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03268B
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H23 N O3 S, C4 H8 O'
_chemical_formula_sum            'C33 H31 N O4 S'
_chemical_formula_weight         537.65
_chemical_name_common            (S,S)-3fa
_chemical_name_systematic
(E)-5-(1,3-diphenylallyl)-4,5-diphenyl-5H-1,2,3-oxathiazole-2,2-dioxide
_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
_audit_creation_date             2021-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-03 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.229(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0008(2)
_cell_length_b                   15.0151(3)
_cell_length_c                   10.6877(2)
_cell_measurement_reflns_used    16352
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.8380
_cell_measurement_theta_min      1.9990
_cell_volume                     1379.61(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector
'Hybrid Pixel Array Detector HyPix Bantam 3000'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00   6.78  368
  2  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00  55.34  368
  3  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00 112.35  368
  4  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00 -30.00  368
  5  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00  30.00  368
  6  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00 -38.15  368
  7  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00  90.00  368
  8  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00  44.73  368
  9  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00  60.00  368
 10  \w    -74.00  63.50   0.50    5.00    --   20.00  54.00  60.00  275
 11  \w    -74.00 110.00   0.50    5.00    --   20.00  54.00 120.00  368
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0612034000
_diffrn_orient_matrix_UB_12      0.0295361000
_diffrn_orient_matrix_UB_13      0.0313178000
_diffrn_orient_matrix_UB_21      0.0437155000
_diffrn_orient_matrix_UB_22      -0.0362722000
_diffrn_orient_matrix_UB_23      0.0347741000
_diffrn_orient_matrix_UB_31      0.0338881000
_diffrn_orient_matrix_UB_32      -0.0066214000
_diffrn_orient_matrix_UB_33      -0.0513605000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44315
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.125
_diffrn_reflns_theta_min         1.995
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       irregular
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method 'Hexane layered on THF'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         7355
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0513P)^2^+0.2076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                6459
_reflns_number_total             7355
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03268b2.cif
_cod_data_source_block           (SS)-3fa_exp_289_hp
_cod_original_cell_volume        1379.60(5)
_cod_database_code               1564388
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C29H23N1O3S1
_chemical_oxdiff_usercomment     'E70_C-allyated Major'
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.934
_diffrn_oxdiff_digest_frames
;
01a974c3bbd28b299f272504c698ec8537039554902
;
_diffrn_oxdiff_digest_hkl
;
01f2900eb31deb970f130b5285549ab4700183
;
_reflns_odcompleteness_completeness 99.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2T(H2TA,H2TB), C3T(H3TA,H3TB), C4T(H4TA,H4TB), C5T(H5TA,H5TB)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
  C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              27241
_olex2_exptl_crystal_mounting_method 'MiTeGen mount + N-Paratone'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.085
_oxdiff_exptl_absorpt_empirical_full_min 0.909