Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.
Liu, Wei; Ali, Siraj Z.; Ammann, Stephen E.; White, M. Christina; Journal of the American Chemical Society 140 (2018) 10658–10662; doi:10.1021/jacs.8b05668

data_4132692
_publ_contact_author
; 
M. Christina White 
University of Illinois 
Department of Chemistry 
600 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10658
_journal_page_last               10662
_journal_paper_doi               10.1021/jacs.8b05668
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         ' C26 H29 N O7 S '
_chemical_formula_sum            'C26 H29 N O7 S'
_chemical_formula_weight         499.56
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
; 
? 
;
_cell_angle_alpha                74.9956(16)
_cell_angle_beta                 81.3175(16)
_cell_angle_gamma                71.4936(14)
_cell_formula_units_Z            2
_cell_length_a                   8.1073(3)
_cell_length_b                   12.6392(5)
_cell_length_c                   13.2065(6)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.62
_cell_volume                     1236.03(9)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2014)'
_computing_data_collection       'APEX3 V2016.9-0 (Bruker, 2016)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/7 (Krause et al., 2015) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-7 (Bruker, 2014), CrystalMaker v2.7.7 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2014-7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014-7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  dd95is
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            102095
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_min         2.620
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/7 (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_id                dd95is
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research with the (2 3 1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack (1983),  6110 Friedels'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       0.0170(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     675
_refine_ls_number_reflns         12247
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0382P)^2^+0.4147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                10855
_reflns_number_total             12247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05668_si_006.cif
_cod_data_source_block           dd95is
_cod_original_cell_volume        1236.04(9)
_cod_database_code               4132692
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              43093
_shelx_hkl_checksum              88453