Symmetric Diarylsulfoxides as Asymmetric Sulfinylating Reagents for Dialkylmagnesium Compounds.
Ruppenthal, Simon; Brückner, Reinhard; The Journal of organic chemistry 80 (2014) 897–; doi:10.1021/jo502417j

data_4030554
_publ_section_title
;
 Symmetric Diarylsulfoxides as Asymmetric Sulfinylating Reagents for
 Dialkylmagnesium Compounds.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              897
_journal_paper_doi               10.1021/jo502417j
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety         'C16 H18 O S'
_chemical_formula_sum            'C16 H18 O S'
_chemical_formula_weight         258.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 104.046(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4665(7)
_cell_length_b                   7.6859(3)
_cell_length_c                   16.0670(11)
_cell_measurement_reflns_used    43718
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1373.65(14)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-97 (Giacovazzo, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'long-fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12212
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.401
_diffrn_reflns_theta_min         1.831
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5635
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0721P)^2^+0.0571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                5025
_reflns_number_total             5635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502417j_si_003.cif
_cod_data_source_block           mk538al
_cod_original_cell_volume        1373.66(14)
_cod_database_code               4030554
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-3
_shelx_res_checksum              33320
_shelx_hkl_checksum              95920