Asymmetric α-Sulfonyl- and α-Phosphoryl-Oxylation of Ketones by a Chiral Hypervalent Iodine(III).
Levitre, Guillaume; Dumoulin, Audrey; Retailleau, Pascal; Panossian, Armen; Leroux, Frédéric R; Masson, Géraldine; The Journal of organic chemistry 82 (2017) 11877–11883; doi:10.1021/acs.joc.7b01597

data_4033317
_publ_section_title
;
 Asymmetric \a-Sulfonyl- and \a-Phosphoryl-Oxylation of Ketones by a
 Chiral Hypervalent Iodine(III).
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11877
_journal_page_last               11883
_journal_paper_doi               10.1021/acs.joc.7b01597
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H16 Cl I O S'
_chemical_formula_sum            'C16 H16 Cl I O S'
_chemical_formula_weight         418.70
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-06-23
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6895(4)
_cell_length_b                   12.8374(5)
_cell_length_c                   17.1516(6)
_cell_measurement_reflns_used    6032
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5650
_cell_measurement_theta_min      3.9770
_cell_volume                     1693.09(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'HPAD Dectris PILATUS 3R 200 K'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     13.00  58.00   0.50    4.00    --    6.60  19.00-150.00   90
  2  \w     13.00  58.00   0.50    4.00    --    6.60  19.00-150.00   90
  3  \w    -15.00  11.00   0.50    4.00    --    6.60  38.00-180.00   52
  4  \w    -41.00  86.00   0.50    4.00    --    6.60  38.00 -60.00  254
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'confocal Max-Flux multilayer optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11923
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.867
_diffrn_reflns_theta_min         3.559
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku mm003 (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1192 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(12)
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0267P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0571
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.788
_reflns_number_gt                3265
_reflns_number_total             3756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01597_si_002.cif
_cod_data_source_block           exp_1
_cod_database_code               4033317
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              20158
_shelx_hkl_checksum              65875