Unexpected Formation of N-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes
Codruţa C. Paraschivescu; Mihaela Matache; Cristian Dobrotă; Alina Nicolescu; Cătălin Maxim; Călin Deleanu; Ileana C. Fărcăşanu; Niculina D. Hădade; Journal of Organic Chemistry 78 (2013) 2670–2679; doi:10.1021/jo400023z

data_4028068
_publ_section_title
;
 Unexpected Formation of N-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides
 and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2670
_journal_page_last               2679
_journal_paper_doi               10.1021/jo400023z
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C28 H30 N4 O8'
_chemical_formula_weight         550.56
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 97.125(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2036(18)
_cell_length_b                   14.2650(15)
_cell_length_c                   18.965(3)
_cell_measurement_reflns_used    200
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     2739.1(7)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  area-detector
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56080
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11036
_diffrn_reflns_theta_full        19.50
_diffrn_reflns_theta_max         19.50
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0778
_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^)+(0.0539P)^2^+2.5911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1709
_reflns_number_gt                2791
_reflns_number_total             4608
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400023z_si_002.cif
_cod_data_source_block           boxa22
_cod_database_code               4028068