S~N~2 Reaction of Sulfur Nucleophiles with Hindered Sulfamidates: Enantioselective Synthesis of α-Methylisocysteine
Alberto Avenoza; Jesús H. Busto; Gonzalo Jiménez-Osés; Jesús M. Peregrina; Journal of Organic Chemistry 71 (2006) 1692–1695; doi:10.1021/jo051632c

data_4021473
_publ_contact_author_email       alberto.avenoza@dq.unirioja.es
_publ_contact_author_name        'Alberto Avenoza'
_publ_section_title
;
 S~N~2 Reaction of Sulfur Nucleophiles with Hindered Sulfamidates:
 Enantioselective Synthesis of \a-Methylisocysteine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1692
_journal_page_last               1695
_journal_paper_doi               10.1021/jo051632c
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C27 H30 N2 O5 S2'
_chemical_formula_weight         526.65
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.0630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.1040(4)
_cell_length_b                   6.1600(2)
_cell_length_c                   16.0640(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1330.96(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0805
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11456
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.240
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.14(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5173
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0666P)^2^+0.1172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                3707
_reflns_number_total             5173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo051632csi20051006_044509.cif
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4021473