Metal-free O-H/C-H difunctionalization of phenols by o-hydroxyarylsulfonium salts in water.
Chen, Dengfeng; Feng, Qingyuan; Yang, Yunqin; Cai, Xu-Min; Wang, Fei; Huang, Shenlin; Chemical science 8 (2017) 1601–1606; doi:10.1039/c6sc04504a

data_1544483
_publ_section_title
;
 Metal-free O-H/C-H difunctionalization of phenols by
 o-hydroxyarylsulfonium salts in water.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              1601
_journal_page_last               1606
_journal_paper_doi               10.1039/c6sc04504a
_journal_volume                  8
_journal_year                    2017
_chemical_formula_sum            'C11 H8.5 F1.5 O2 S'
_chemical_formula_weight         233.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-04 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.386(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.0792(9)
_cell_length_b                   14.673(2)
_cell_length_c                   23.976(4)
_cell_measurement_reflns_used    8190
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      2.78
_cell_volume                     2138.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31921
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.776
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0640
_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^)+(0.0596P)^2^+2.3315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2648
_reflns_number_total             3763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc04504a2.cif
_cod_data_source_block           1
_cod_depositor_comments
;Adding full bibliography for 1544481--1544483.cif.

 Adding full bibliography for 1544481--1544483.cif.
;
_cod_original_formula_sum        'C11 H8.50 F1.50 O2 S'
_cod_database_code               1544483
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              38816