Efficient and Stereoselective Nitration of Mono- and Disubstituted Olefins with AgNO2 and TEMPO
Soham Maity; Srimanta Manna; Sujoy Rana; Togati Naveen; Arijit Mallick; Debabrata Maiti; Journal of the American Chemical Society 135 (2013) 3355–3358; doi:10.1021/ja311942e

data_4119410
_publ_section_title
;
 Efficient and Stereoselective Nitration of Mono- and Disubstituted
 Olefins with AgNO2 and TEMPO
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3355
_journal_page_last               3358
_journal_paper_doi               10.1021/ja311942e
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C11 H10 N0 O2'
_chemical_formula_weight         174.19
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2xa'
_symmetry_space_group_name_H-M   'P 21 1 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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            7
_cell_length_a                   8.0513(4)
_cell_length_b                   10.4170(6)
_cell_length_c                   19.4576(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1631.92(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.835
_diffrn_measured_fraction_theta_max 0.695
_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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5033
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.08
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             644
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.4(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         3999
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.080
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.2598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                3254
_reflns_number_total             3999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja311942e_si_003.cif
_cod_data_source_block           dmaiti0805
_cod_database_code               4119410