Asymmetric Synthesis of (S)-(-)-Xylopinine. Use of the Sulfinyl Group as an Ipso Director in Aromatic SE
Virginia M. Mastranzo; Francisco Yuste; Benjamín Ortiz; Rubén Sánchez-Obregón; Rubén A. Toscano; José L. García Ruano; Journal of Organic Chemistry 76 (2011) 5036–5041; doi:10.1021/jo2007237

data_4026396
_publ_section_title
;
 Asymmetric Synthesis of (S)-(-)-Xylopinine. Use of the Sulfinyl Group as
 an Ipso Director in Aromatic SE
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5036
_journal_page_last               5041
_journal_paper_doi               10.1021/jo2007237
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C34 H37 N O6 S2, (C4 H8 O2)0.5'
_chemical_formula_sum            'C36 H41 N O7 S2'
_chemical_formula_weight         663.82
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.459(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.779(3)
_cell_length_b                   12.9861(15)
_cell_length_c                   8.9843(10)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.27
_cell_volume                     3471.1(7)
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 6.23C (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 0.661
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Smart Apex CCD diffractometer 01-670'
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19237
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_correction_T_min  0.9344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.142
_platon_squeeze_details
; 
The unit cell contains two ethyl acetate molecules disordered over (at least) 
two sites which have been treated as a diffuse contribution to the overall 
scattering without specific atom positions by SQUEEZE/PLATON
;
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         6363
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+1.8749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                6170
_reflns_number_total             6363
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2007237_si_001.cif
_cod_data_source_block           Compound_6b
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4026396