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_1564387
_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_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_chemical_name_common            4aa
_chemical_name_systematic
'(E)-3-(hex-2-en-1-yl)-4,5-diphenyl-3H-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                   8.4602(2)
_cell_length_b                   10.8079(3)
_cell_length_c                   19.9865(5)
_cell_measurement_reflns_used    9401
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.2530
_cell_measurement_theta_min      2.6080
_cell_volume                     1827.51(8)
_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 HPC-3000'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_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    8.00    --   20.00  54.00-180.00  368
  2  \w    -74.00 110.00   0.50    8.00    --   20.00  54.00 -90.00  368
  3  \w    -74.00 110.00   0.50    8.00    --   20.00  54.00-150.00  368
  4  \w    -74.00 110.00   0.50    8.00    --   20.00  54.00  90.00  368
  5  \w    -74.00 -14.00   0.50    8.00    --   20.00  54.00   0.00  120
;
_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      0.0745310000
_diffrn_orient_matrix_UB_12      -0.0287696000
_diffrn_orient_matrix_UB_13      -0.0045899000
_diffrn_orient_matrix_UB_21      0.0124440000
_diffrn_orient_matrix_UB_22      0.0005320000
_diffrn_orient_matrix_UB_23      0.0350913000
_diffrn_orient_matrix_UB_31      -0.0362969000
_diffrn_orient_matrix_UB_32      -0.0590071000
_diffrn_orient_matrix_UB_33      0.0025531000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25213
_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         29.574
_diffrn_reflns_theta_min         2.142
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97951
_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    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method 'n-hexane / Et2O'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5129
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0443P)^2^+0.1702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4349
_reflns_number_total             5129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03268b2.cif
_cod_data_source_block           4aa_exp_193_hp
_cod_database_code               1564387
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C20H21N1O3S1
_chemical_oxdiff_usercomment     E39_N-allylated
_diffrn_oxdiff_digest_frames
;
01a1e9ca629c856e4e0eee49d0f02f582b015924c7d
;
_diffrn_oxdiff_digest_hkl
;
013201017eaa2287495ce3a68e8db58a5ba2d7
;
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.80(8)
 0.20(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C5-C4 = C5A-C4
 1.5 with sigma of 0.01
 C6-C5 = C6A-C5A
 1.53 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
5. Others
 Sof(H4BC)=Sof(H4BD)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=
 Sof(H6AC)=1-FVAR(1)
 Sof(H4AA)=Sof(H4AB)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=
 Sof(H6C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4AA,H4AB), C4(H4BC,H4BD), C5(H5A,H5B), C5A(H5AA,H5AB)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C52(H52),
 C53(H53), C54(H54), C55(H55), C56(H56)
6.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC)
;
_shelx_res_checksum              79821
_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 1.052
_oxdiff_exptl_absorpt_empirical_full_min 0.965