Copper-catalyzed aerobic carboxygenation and N-arylation of [1,2,3]triazolo[1,5-a]pyridines towards pyridinium triazolinone ylides
Sreekumar Pankajakshan; Zhi Guang Chng; Rakesh Ganguly; Teck Peng Loh; Chem.Commun. 51 (2015) 5929–; doi:10.1039/C4cc10061A

data_7116831
_publ_section_title
;
 Copper-catalyzed aerobic carboxygenation and N-arylation of
 [1,2,3]triazolo[1,5-a]pyridines towards pyridinium triazolinone ylides
;
_journal_name_full               Chem.Commun.
_journal_page_first              5929
_journal_paper_doi               10.1039/C4cc10061A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C12 H9 N3 O'
_chemical_formula_weight         211.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2014-11-20 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.778(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.477(3)
_cell_length_b                   8.789(2)
_cell_length_c                   19.955(6)
_cell_measurement_reflns_used    3001
_cell_measurement_temperature    443.(2)
_cell_measurement_theta_max      30.5944
_cell_measurement_theta_min      2.9516
_cell_volume                     1955.0(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      443.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19517
_diffrn_reflns_theta_full        31.06
_diffrn_reflns_theta_max         31.06
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.7578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                2235
_reflns_number_total             3133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc10061a21.cif
_cod_data_source_block           I_a
_cod_database_code               7116831
_shelx_res_checksum              19369
_shelx_hkl_checksum              41118