2-Trimethylsilylethanesulfonyl (SES) versus Tosyl (Ts) Protecting Group in the Preparation of Nitrogen-Containing Five-Membered Rings. A Novel Route for the Synthesis of Substituted Pyrrolines and Pyrrolidines
Declerck, Valérie; Allouchi, Hassan; Martinez, Jean; Lamaty, Frédéric; The Journal of Organic Chemistry 72 (2007) 1518–1521; doi:10.1021/jo062239p

data_4028897
_publ_section_title
;
 2-Trimethylsilylethanesulfonyl (SES) versus Tosyl (Ts) Protecting Group
 in the Preparation of Nitrogen-Containing Five-Membered Rings. A Novel
 Route for the Synthesis of Substituted Pyrrolines and Pyrrolidines
;
_journal_issue                   4
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              1518
_journal_page_last               1521
_journal_paper_doi               10.1021/jo062239p
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C18 H18 N2 O6 S'
_chemical_formula_weight         390.40
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2n -2ac'
_symmetry_space_group_name_H-M   'P c 21 n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.5353(3)
_cell_length_b                   21.1912(16)
_cell_length_c                   22.4218(9)
_cell_measurement_temperature    170(2)
_cell_volume                     3580.4(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.8 (release 17-03-2006 CrysAlis171 .NET)
(compiled Mar 17 2006,10:57:34)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.8 (release 17-03-2006 CrysAlis171 .NET)
(compiled Mar 17 2006,10:57:34)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.8 (release 17-03-2006 CrysAlis171 .NET)
(compiled Mar 17 2006,10:57:34)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 8.3622
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'CCD DETECTOR KM4CCD/SAPPHIRE, X-Calibur'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            22589
_diffrn_reflns_theta_full        29.23
_diffrn_reflns_theta_max         29.23
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.24414
_exptl_absorpt_correction_T_min  0.80884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.8 (release 17-03-2006 CrysAlis171 .NET)
(compiled Mar 17 2006,10:57:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.030
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         8727
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0725
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0978P)^2^+3.1753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1892
_reflns_number_gt                6653
_reflns_number_total             8727
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062239psup1.cif
_cod_data_source_block           vd1232h
_cod_original_sg_symbol_H-M      Pc21n
_cod_database_code               4028897