Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution
Michł Achmatowicz; Oliver R. Thiel; Gilles Gorins; Corinne Goldstein; Caroline Affouard; Randy Jensen; Robert D. Larsen; Journal of Organic Chemistry 73 (2008) 6793–6799; doi:10.1021/jo801131z

data_4023651
_publ_section_title
;
 Selective Ortho Methylation of Nitroheteroaryls
 by Vicarious Nucleophilic Substitution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6793
_journal_page_last               6799
_journal_paper_doi               10.1021/jo801131z
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C13 H12 N2 O4'
_chemical_formula_sum            'C13 H12 N2 O4'
_chemical_formula_weight         260.25
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.039(2)
_cell_angle_beta                 85.665(2)
_cell_angle_gamma                84.080(2)
_cell_formula_units_Z            4
_cell_length_a                   8.1460(11)
_cell_length_b                   10.3097(14)
_cell_length_c                   14.933(2)
_cell_measurement_reflns_used    4011
_cell_measurement_temperature    446(2)
_cell_measurement_theta_max      26.84
_cell_measurement_theta_min      2.84
_cell_volume                     1185.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      446(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15250
_diffrn_reflns_theta_full        27.31
_diffrn_reflns_theta_max         27.31
_diffrn_reflns_theta_min         2.08
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0038(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0520P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                3778
_reflns_number_total             5334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801131z-file002.cif
_cod_data_source_block           aramg107_0m
_cod_database_code               4023651