Palladium-Catalyzed Enantioselective Arylation of Aryl Sulfenate Anions: A Combined Experimental and Computational Study.
Jia, Tiezheng; Zhang, Mengnan; McCollom, Samuel P.; Bellomo, Ana; Montel, Sonia; Mao, Jianyou; Dreher, Spencer D.; Welch, Christopher J.; Regalado, Erik L.; Williamson, R. Thomas; Manor, Brian C.; Tomson, Neil C.; Walsh, Patrick J.; Journal of the American Chemical Society 139 (2017) 8337–8345; doi:10.1021/jacs.7b03623

data_4131300
_publ_section_title
;
 Palladium-Catalyzed Enantioselective Arylation of Aryl Sulfenate Anions:
 A Combined Experimental and Computational Study.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8337
_journal_page_last               8345
_journal_paper_doi               10.1021/jacs.7b03623
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C16 H18 O S'
_chemical_formula_sum            'C16 H18 O S'
_chemical_formula_weight         258.36
_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     direct
_audit_creation_date             2016-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7924(3)
_cell_length_b                   8.1095(3)
_cell_length_c                   29.6243(13)
_cell_measurement_reflns_used    9763
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.58
_cell_volume                     1391.56(11)
_computing_data_collection       'Bruker APEX3 v2016.1-0'
_computing_data_reduction        'Bruker SAINT v8.37A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'CMOS area detector'
_diffrn_measurement_device_type  'Bruker D8QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            76050
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         3.251
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0401P)^2^+0.3189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3164
_reflns_number_total             3209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b03623_si_001.cif
_cod_data_source_block           6213
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_exptl_crystal_color' was replaced with
'_exptl_crystal_colour' as specified in the replacement file
'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               4131300