Pd-Catalyzed Site-Selective p-Hydroxyphenyloxylation of Benzylic α-C(sp<sup>3</sup>)-H Bonds with 1,4-Benzoquinone.
Song, Guangjun; Zheng, Ziwei; Wang, Yanhui; Yu, Xinhong; Organic letters 18 (2016) 6002–6005; doi:10.1021/acs.orglett.6b02782

data_1555867
_publ_section_title
;
 Pd-Catalyzed Site-Selective p-Hydroxyphenyloxylation of Benzylic
 \a-C(sp<sup>3</sup>)-H Bonds with 1,4-Benzoquinone.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6002
_journal_page_last               6005
_journal_paper_doi               10.1021/acs.orglett.6b02782
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H18 Cl N O2 S'
_chemical_formula_weight         335.83
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.072(4)
_cell_length_b                   12.922(6)
_cell_length_c                   15.704(7)
_cell_measurement_reflns_used    769
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.547
_cell_measurement_theta_min      5.180
_cell_volume                     1638.0(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1544
_diffrn_reflns_av_unetI/netI     0.1748
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8741
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.041
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
; 
 Flack x determined using 368 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.18(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0816
_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^)+(0.0694P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1428
_reflns_number_total             2885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cd15310.cif
_cod_data_source_block           cd15310
_cod_original_cell_volume        1638.2(13)
_cod_database_code               1555867
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2013-4
_shelx_res_checksum              21809
_shelx_hkl_checksum              42640