Rh2(II)-Catalyzed Nitro-Group Migration Reactions: Selective Synthesis of 3-Nitroindoles from β-Nitro Styryl Azides
Benjamin J. Stokes; Sheng Liu; Tom G. Driver; Journal of the American Chemical Society 133 (2011) 4702–4705; doi:10.1021/ja111060q

data_4105871
_publ_section_title
;
 Rh2(II)-Catalyzed Nitro-Group Migration Reactions: Selective Synthesis of
 3-Nitroindoles from \b-Nitro Styryl Azides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4702
_journal_page_last               4705
_journal_paper_doi               10.1021/ja111060q
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C15 H18 N3 O2 S'
_chemical_formula_weight         305.28
_chemical_name_systematic
; 
 ? 
;
_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                   7.6089(5)
_cell_length_b                   11.0529(8)
_cell_length_c                   15.9060(11)
_cell_measurement_temperature    298(2)
_cell_volume                     1337.70(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12356
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9019
_exptl_absorpt_correction_T_min  0.8848
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.65(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.935
_refine_ls_shift/su_mean         0.037
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2802
_reflns_number_total             3081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja111060q_si_001.cif
_cod_data_source_block           cdwtd1m
_cod_database_code               4105871