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_1564390
_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         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_chemical_name_common            3aa
_chemical_name_systematic
(E)-5-(hex-2-en-1-yl)-4,5-diphenyl-5H-1,2,3-oxathiazole-2,2-dioxide
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0914(4)
_cell_length_b                   10.2497(4)
_cell_length_c                   18.7657(7)
_cell_measurement_reflns_used    6046
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      20.2850
_cell_measurement_theta_min      2.1510
_cell_volume                     1941.01(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_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_temperature      293.0(10)
_diffrn_detector                 'HyPix Bantam HPC-3000'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   20.00    --   20.00  54.00-150.00  368
  2  \w    -74.00 110.00   0.50   20.00    --   20.00  54.00 120.00  368
  3  \w    -74.00 110.00   0.50   20.00    --   20.00  54.00 120.00  368
  4  \w    -74.00 110.00   0.50   20.00    --   20.00  54.00 -60.00  368
  5  \w    -40.00  71.00   0.50   20.00    --   20.00  54.00-180.00  222
  6  \w    -74.00  57.00   0.50   20.00    --   20.00  54.00  30.00  262
;
_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      0.0506525000
_diffrn_orient_matrix_UB_12      0.0449062000
_diffrn_orient_matrix_UB_13      -0.0091944000
_diffrn_orient_matrix_UB_21      -0.0305448000
_diffrn_orient_matrix_UB_22      0.0482571000
_diffrn_orient_matrix_UB_23      0.0215842000
_diffrn_orient_matrix_UB_31      0.0379270000
_diffrn_orient_matrix_UB_32      -0.0211771000
_diffrn_orient_matrix_UB_33      0.0296269000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32513
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_min         2.171
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
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    1.216
_exptl_crystal_description       irregular
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method 'layering hexane on THF'
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 960 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5428
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0790P)^2^+0.0970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2990
_reflns_number_total             5428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03268b2.cif
_cod_data_source_block           3aa_exp_291
_cod_database_code               1564390
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C20H21N1O3S1
_chemical_oxdiff_usercomment     E39_C-allylated
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.896
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_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
2. Restrained distances
 C18-C16
 2.5 with sigma of 0.01
 C16-C15 \\sim C17-C16 \\sim C18-C17
 with sigma of 0.005
3. Rigid bond restraints
 C16, C17, C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B)
4.b Me refined with riding coordinates:
 C18(H18A,H18B,H18C)
4.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), C14(H14), C15(H15)
;
_shelx_res_checksum              22522
_olex2_exptl_crystal_mounting_method 'MiTeGen mount + 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 1.120
_oxdiff_exptl_absorpt_empirical_full_min 0.915