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_4132691
_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         'C36 H42 O7'
_chemical_formula_sum            'C36 H42 O7'
_chemical_formula_weight         586.69
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9410(3)
_cell_length_b                   13.1806(3)
_cell_length_c                   18.8817(4)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.42
_cell_volume                     3220.65(12)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/5, (Bruker, 2012 & 2014) 
;
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_wavelength_id  dd27esa
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26546
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.447
_diffrn_reflns_theta_min         4.090
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.9388
_exptl_absorpt_correction_T_min  0.8218
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1256
_exptl_crystal_id                dd27esa
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Paratone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (3 -2 3) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack (1983),  2578 Friedels'
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5895
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0417P)^2^+1.0499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5567
_reflns_number_total             5895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05668_si_004.cif
_cod_data_source_block           dd27esa
_cod_database_code               4132691
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.797
_shelx_estimated_absorpt_t_max   0.926
_shelx_res_checksum              7955
_shelx_hkl_checksum              29779