Pd-Catalyzed Oxidative Annulation of Hydrazides with Isocyanides: Synthesis of 2-Amino-1,3,4-oxadiazoles.
Fang, Tao; Tan, Qitao; Ding, Zhengwei; Liu, Bingxin; Xu, Bin; Organic letters 16 (2014) 2342–2345; doi:10.1021/ol5006449

data_1514335
_publ_section_title
;
 Pd-Catalyzed Oxidative Annulation of Hydrazides with Isocyanides:
 Synthesis of 2-Amino-1,3,4-oxadiazoles.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2342
_journal_page_last               2345
_journal_paper_doi               10.1021/ol5006449
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 104.354(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.276(4)
_cell_length_b                   6.8223(14)
_cell_length_c                   13.030(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1660.0(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5214
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.075
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0059(14)
_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   1.035
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0831P)^2^+0.4041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1571
_reflns_number_gt                1454
_reflns_number_total             2050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5006449_si_002.cif
_cod_data_source_block           ft31
_cod_depositor_comments          'Adding full bibliography for 1514335.cif.'
_cod_original_cell_volume        1660.1(6)
_cod_original_sg_symbol_H-M      'c 2/m'
_cod_database_code               1514335