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_1564386
_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            (rac)-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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-03
_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                82.217(3)
_cell_angle_beta                 83.123(3)
_cell_angle_gamma                67.004(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9169(3)
_cell_length_b                   10.0932(3)
_cell_length_c                   10.9734(4)
_cell_measurement_reflns_used    10939
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.6180
_cell_measurement_theta_min      2.4760
_cell_volume                     898.33(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.48a (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      150.00(10)
_diffrn_detector                 'HyPix Bantam HPC-3000'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.955
_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    4.00    --   20.00  54.00 -26.84  368
  2  \w    -74.00 110.00   0.50    4.00    --   20.00  54.00 -26.84  368
  3  \w    -74.00 110.00   0.50    4.00    --   20.00  54.00-129.88  368
  4  \w    -74.00 110.00   0.50    4.00    --   20.00  54.00  30.00  368
  5  \w    -74.00 110.00   0.50    4.00    --   20.00  54.00  86.03  368
  6  \w    -74.00 110.00   0.50    4.00    --   20.00  54.00-180.00  368
  7  \w    -74.00 110.00   0.50    4.00    --   20.00  54.00 -90.00  368
  8  \w    -74.00 110.00   0.50    4.00    --   20.00  54.00 -60.00  368
  9  \w    -74.00 -66.50   0.50    4.00    --   20.00  54.00 -60.00   15
;
_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      -0.0121738000
_diffrn_orient_matrix_UB_12      -0.0380026000
_diffrn_orient_matrix_UB_13      -0.0453000000
_diffrn_orient_matrix_UB_21      -0.0189544000
_diffrn_orient_matrix_UB_22      -0.0476543000
_diffrn_orient_matrix_UB_23      0.0471832000
_diffrn_orient_matrix_UB_31      -0.0836662000
_diffrn_orient_matrix_UB_32      0.0465642000
_diffrn_orient_matrix_UB_33      0.0008659000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23029
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_min         2.202
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.48a (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    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method 'Et2O evaporation'
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0544P)^2^+0.2355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4661
_reflns_number_total             5236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03268b2.cif
_cod_data_source_block           (rac)-3aa_exp_192_hp
_cod_original_cell_volume        898.33(5)
_cod_database_code               1564386
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C20H21NO3S
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.897
_reflns_odcompleteness_completeness 95.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.a Secondary CH2 refined with riding coordinates:
 C1H(H1HA,H1HB), C4H(H4HA,H4HB), C5H(H5HA,H5HB)
2.b Aromatic/amide H refined with riding coordinates:
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C52(H52), C53(H53),
 C54(H54), C55(H55), C56(H56), C2H(H2H), C3H(H3H)
2.c Idealised Me refined as rotating group:
 C6H(H6HA,H6HB,H6HC)
;
_shelx_res_checksum              47896
_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 1.161
_oxdiff_exptl_absorpt_empirical_full_min 0.920