Intramolecular decarboxylative coupling as the key step in copper-catalyzed domino reaction: facile access to 2-(1,3,4-oxadiazol-2-yl)aniline derivatives
Cheng Xu; Feng-Cheng Jia; Qun Cai; Deng-Kui Li; Zhi-Wen Zhou; An-Xin Wu; Chem.Commun. 51 (2015) 6629–; doi:10.1039/C5cc01116G

data_7116909
_publ_section_title
;
 Intramolecular decarboxylative coupling as the key step in
 copper-catalyzed domino reaction: facile access to
 2-(1,3,4-oxadiazol-2-yl)aniline derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              6629
_journal_paper_doi               10.1039/C5cc01116G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C12 H9 N3 O2'
_chemical_formula_weight         227.22
_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
_audit_update_record
;
2014-11-18 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   11.5359(11)
_cell_length_b                   15.7377(15)
_cell_length_c                   23.975(2)
_cell_measurement_reflns_used    323
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      1.7
_cell_volume                     4352.6(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II Smart CCD'
_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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            31955
_diffrn_reflns_theta_full        26.21
_diffrn_reflns_theta_max         26.21
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4367
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0763P)^2^+1.1946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1583
_reflns_number_gt                3031
_reflns_number_total             4367
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01116g2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7116909