Sulfoxide-alkene hybrids: a new class of chiral ligands for the Hayashi-Miyaura reaction.
Thaler, Tobias; Guo, Li-Na; Steib, Andreas K.; Raducan, Mihai; Karaghiosoff, Konstantin; Mayer, Peter; Knochel, Paul; Organic letters 13 (2011) 3182–3185; doi:10.1021/ol200841x

data_1502188
_publ_section_title
;
 Sulfoxide-alkene hybrids: a new class of chiral ligands for the
 Hayashi-Miyaura reaction.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3182
_journal_page_last               3185
_journal_paper_doi               10.1021/ol200841x
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H22 O2 S'
_chemical_formula_sum            'C21 H22 O2 S'
_chemical_formula_weight         338.464
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                C21H22O2S_oo006_knochel
_audit_creation_date
;
'Wed Jan 13 12:51:47 2010'
;
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             13-Jan-10
_cell_angle_alpha                90.00
_cell_angle_beta                 90.051(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4230(4)
_cell_length_b                   7.4429(5)
_cell_length_c                   17.9557(12)
_cell_measurement_reflns_used    3159
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.2496
_cell_measurement_theta_min      4.1878
_cell_volume                     858.39(10)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -52.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931   77.0000  -60.0000 98

  2 omega  -53.00   50.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931   77.0000   60.0000 103

  3 omega  -53.00  -21.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931   77.0000  -30.0000 32

  4 omega   15.00   52.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931   77.0000  -30.0000 37

  5 omega  -52.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931   77.0000 -150.0000 85

  6 omega   46.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2306   77.0000 -180.0000 25

  7 omega  -10.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2306   77.0000 -180.0000 49

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0782899623
_diffrn_orient_matrix_UB_12      0.0638246256
_diffrn_orient_matrix_UB_13      -0.0088588762
_diffrn_orient_matrix_UB_21      -0.0100830353
_diffrn_orient_matrix_UB_22      -0.0383788036
_diffrn_orient_matrix_UB_23      -0.0359604830
_diffrn_orient_matrix_UB_31      -0.0772317314
_diffrn_orient_matrix_UB_32      -0.0594836669
_diffrn_orient_matrix_UB_33      0.0137194727
_diffrn_radiation_collimation    '0.5 mm collimator'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6431
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         4.19
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.30952(15)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0477P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                2754
_reflns_number_total             3349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200841x_si_002.cif
_cod_data_source_block           oo006
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1502188