General Route to Racemic and Enantiomeric Carbo- and Heterocyclic Vinyl Sulfoxides via Tandem Michael Addition/Horner Olefination of α-Phosphorylvinyl Sulfoxides
Marian Mikołajczyk; Jerzy A. Krysiak; Wanda H. Midura; Michał W. Wieczorek; Ewa Róz̀ycka-Sokołowska; Journal of Organic Chemistry 71 (2006) 8818–8823; doi:10.1021/jo061463b

data_4022068
_publ_contact_author_address
;Institute of Chemistry and Environmental Protection
Jan D\/lugosz University
ul. Armii Krajowej 13/15
42-200 Cz\;estochowa
Poland
;
_publ_contact_author_email       abalinska@poczta.onet.pl
_publ_contact_author_fax         '+48 034 3665322'
_publ_contact_author_name        'Wieczorek Micha\/l'
_publ_contact_author_phone       '+48 034 3614918'
_publ_section_title
;
 General Route to Racemic and Enantiomeric Carbo- and Heterocyclic
 Vinyl Sulfoxides via Tandem Michael Addition/Horner Olefination of
 \a-Phosphorylvinyl Sulfoxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8818
_journal_page_last               8823
_journal_paper_doi               10.1021/jo061463b
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H13 N O S'
_chemical_formula_sum            'C14 H13 N O S'
_chemical_formula_weight         243.32
_chemical_name_systematic
;
 (S)-6-(p-Toluenesulfinyl)-3H-pyrrolizine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_creation_date             2006-07-19T18:38:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 113.680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7360(10)
_cell_length_b                   5.8110(10)
_cell_length_c                   15.376(2)
_cell_measurement_reflns_used    3915
_cell_measurement_temperature    568(2)
_cell_measurement_theta_max      72.51
_cell_measurement_theta_min      5.37
_cell_volume                     1205.8(3)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 1995-2003)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 1995-2003)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 1995-2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      568(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Xcalibur TM 3 CCD diffractometer'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8340
_diffrn_reflns_theta_full        67.89
_diffrn_reflns_theta_max         67.89
_diffrn_reflns_theta_min         5.37
_exptl_absorpt_coefficient_mu    2.227
_exptl_absorpt_correction_T_max  0.7759
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.05
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.0048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+0.3467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                3327
_reflns_number_total             3623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061463bsi20060721_032009.cif
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022068