Pd(II)-Catalyzed Aminotetrazole-directed Ortho-Selective Halogenation of Arenes
Pradeep Sadhu; Santhosh Kumar Alla; Tharmalingam Punniyamurthy; Journal of Organic Chemistry 78 (2013) 6104–6111; doi:10.1021/jo400755q

data_4028349
_publ_section_title
;
 Pd(II)-Catalyzed Aminotetrazole-directed Ortho-Selective Halogenation of
 Arenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6104
_journal_page_last               6111
_journal_paper_doi               10.1021/jo400755q
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C15 H14 I N5'
_chemical_formula_weight         391.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                 90.1540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6397(2)
_cell_length_b                   9.8963(2)
_cell_length_c                   20.2534(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1531.25(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.913
_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  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18980
_diffrn_reflns_theta_full        27.66
_diffrn_reflns_theta_max         27.66
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    2.092
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             768
_refine_diff_density_max         0.551
_refine_diff_density_min         -1.751
_refine_diff_density_rms         0.257
_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     192
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0565P)^2^+0.1663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                2903
_reflns_number_total             3254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400755q_si_001.cif
_cod_data_source_block           11
_cod_database_code               4028349