Synthesis of 2-Amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via Sequential Condensation and I2-Mediated Oxidative C-O/C-S Bond Formation.
Niu, Pengfei; Kang, Jinfeng; Tian, Xianhai; Song, Lina; Liu, Hongxu; Wu, Jie; Yu, Wenquan; Chang, Junbiao; The Journal of organic chemistry 80 (2014) 1018–; doi:10.1021/jo502518c

data_4030394
_publ_section_title
;
 Synthesis of 2-Amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via
 Sequential Condensation and I2-Mediated Oxidative C-O/C-S Bond Formation.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1018
_journal_paper_doi               10.1021/jo502518c
_journal_volume                  80
_journal_year                    2014
_chemical_formula_sum            'C24 H18 N6 O2'
_chemical_formula_weight         422.44
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 99.96(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.496(5)
_cell_length_b                   10.716(2)
_cell_length_c                   11.564(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2745.7(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9016
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9864
_exptl_crystal_density_diffrn    1.022
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.202
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.010
_refine_ls_R_factor_all          0.1768
_refine_ls_R_factor_gt           0.1681
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4836
_refine_ls_wR_factor_ref         0.4900
_reflns_number_gt                2082
_reflns_number_total             2414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502518c_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 4030394.cif.'
_cod_original_cell_volume        2745.8(9)
_cod_database_code               4030394