Dearomatization of aryl sulfoxides: a switch between mono- and dual-difluoroalkylation
Huang, Xin; Zhang, Yage; Liang, Weijian; Zhang, Qifeng; Zhan, Yaling; Kong, Lichun; Peng, Bo; Chemical Science 11 (2020) 3048–3053; doi:10.1039/D0SC00244E

data_1557385
_publ_section_title
;
 Dearomatization of aryl sulfoxides: a switch between mono- and
 dual-difluoroalkylation
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              3048
_journal_page_last               3053
_journal_paper_doi               10.1039/D0SC00244E
_journal_volume                  11
_journal_year                    2020
_chemical_formula_sum            'C33 H29 Cl F4 O4 S2'
_chemical_formula_weight         665.13
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-12-20 deposited with the CCDC.	2020-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                66.7990(10)
_cell_angle_beta                 70.3300(10)
_cell_angle_gamma                75.6270(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2309(5)
_cell_length_b                   13.2445(5)
_cell_length_c                   13.5012(6)
_cell_measurement_reflns_used    9332
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.33
_cell_volume                     1569.19(12)
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'APEX-\/c\`o CCDC'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32938
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  .954
_exptl_absorpt_correction_T_min  .903
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .27
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         7140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0984P)^2^+0.4327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1818
_reflns_number_gt                5151
_reflns_number_total             7140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0sc00244e2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1557384--1557385.cif.

 Adding full bibliography for 1557384--1557385.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1557385
_refine_ls_r_factor_ref          0.0754