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_4026318
_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            'C10 H14 Br N3 O4'
_chemical_formula_weight         320.15
_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            8
_cell_length_a                   7.57500(10)
_cell_length_b                   7.57300(10)
_cell_length_c                   45.4410(10)
_cell_measurement_temperature    293(2)
_cell_volume                     2606.74(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.948
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            6555
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    3.165
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             1296
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0161P)^2^+3.7086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                3934
_reflns_number_total             5144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200479y_si_001_2.cif
_cod_data_source_block           shelxl_2
_cod_database_code               4026318