Stereocontrolled Ring-Opening of a Hindered Sulfamidate with Nitrogen-Containing Aromatic Heterocycles: Synthesis of Chiral Quaternary Imidazole Derivatives
Lara Mata; Gonzalo Jiménez-Osés; Alberto Avenoza; Jesús H. Busto; Jesús M. Peregrina; Journal of Organic Chemistry 76 (2011) 4034–4042; doi:10.1021/jo200479y

data_4026317
_publ_section_title
;
 Stereocontrolled Ring-Opening of a Hindered Sulfamidate with
 Nitrogen-Containing Aromatic Heterocycles: Synthesis of Chiral Quaternary
 Imidazole Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4034
_journal_page_last               4042
_journal_paper_doi               10.1021/jo200479y
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C12 H19 N3 O4'
_chemical_formula_weight         269.30
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   7.4570(4)
_cell_length_b                   9.9060(6)
_cell_length_c                   19.2280(9)
_cell_measurement_temperature    293(2)
_cell_volume                     1420.35(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_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  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7244
_diffrn_reflns_theta_full        28.15
_diffrn_reflns_theta_max         28.15
_diffrn_reflns_theta_min         3.79
_exptl_absorpt_coefficient_mu    0.095
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             576
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0466P)^2^+0.2223P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                2563
_reflns_number_total             3267
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200479y_si_001_1.cif
_cod_data_source_block           shelxl_1
_cod_database_code               4026317