Palladium-Catalyzed Chelation-Assisted Aromatic C-H Nitration: Regiospecific Synthesis of Nitroarenes Free from the Effect of the Orientation Rules
Wei Zhang; Shaojie Lou; Yunkui Liu; Zhenyuan Xu; Journal of Organic Chemistry 78 (2013) 5932–5948; doi:10.1021/jo400594j

data_4028333
_publ_contact_author_address
;
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology
Zhejiang University of Technology
Hangzhou
310014
People's Republic of China
;
_publ_contact_author_email       ykuiliu@zjut.edu.cn
_publ_contact_author_fax         '86 571 88320066'
_publ_contact_author_name        'Mr. Yunkui Liu'
_publ_contact_author_phone       '86 571 88320609'
_publ_section_title
;
 Palladium-Catalyzed Chelation-Assisted Aromatic C-H Nitration:
 Regiospecific Synthesis of Nitroarenes Free from the Effect of the
 Orientation Rules
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5932
_journal_page_last               5948
_journal_paper_doi               10.1021/jo400594j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C15 H11 N3 O3'
_chemical_formula_sum            'C15 H11 N3 O3'
_chemical_formula_weight         281.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.6470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.313(4)
_cell_length_b                   13.882(9)
_cell_length_c                   13.112(7)
_cell_measurement_reflns_used    7945
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     1316.0(13)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rolling anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12321
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       chunk
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.032(3)
_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   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0513P)^2^+0.6842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                1887
_reflns_number_total             2962
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400594j_si_002.cif
_cod_data_source_block           ch114
_cod_original_cell_volume        1315.9(13)
_cod_database_code               4028333