Pd-catalyzed C-H activation/C-N bond formation: a new route to 1-aryl-1H-benzotriazoles.
Kumar, Rapolu Kiran; Ali, Md Ashif; Punniyamurthy, Tharmalingam; Organic letters 13 (2011) 2102–2105; doi:10.1021/ol200523a

data_1502119
_publ_section_title
;
 Pd-catalyzed C-H activation/C-N bond formation: a new route to
 1-aryl-1H-benzotriazoles.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2102
_journal_page_last               2105
_journal_paper_doi               10.1021/ol200523a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C16 H17 N3'
_chemical_formula_sum            'C16 H17 N3'
_chemical_formula_weight         251.3304
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   13.2943(7)
_cell_length_b                   7.4099(4)
_cell_length_c                   27.6216(14)
_cell_measurement_reflns_used    2458
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.58
_cell_measurement_theta_min      2.95
_cell_volume                     2721.0(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0641
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            23783
_diffrn_reflns_theta_full        28.02
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0108(12)
_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   0.995
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                1810
_reflns_number_total             3161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200523a_si_002.cif
_cod_data_source_block           p
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1502119