One-Pot Formation of 1,3,4-Oxadiazol-2(3H)-ones and Dibenzo[c,e]azepines by Concomitant Cathodic Reduction of Diazonium Salts and Phenanthrenequinones
Belen Batanero; Fructuoso Barba; Avelino Martin; Journal of Organic Chemistry 78 (2013) 9477–9481; doi:10.1021/jo401264w

data_4028595
_publ_contact_author_address
;
Departamento de Quimica Organica y Quimica Inorganica
Universidad de Alcala
Alcala de Henares
Madrid, SP
;
_publ_contact_author_email       avelino.martin@uah.es
_publ_contact_author_name        'Martin, Avelino'
_publ_section_title
;
 One-Pot Formation of 1,3,4-Oxadiazol-2(3H)-ones and Dibenzo[c,e]azepines
 by Concomitant Cathodic Reduction of Diazonium Salts and
 Phenanthrenequinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9477
_journal_page_last               9481
_journal_paper_doi               10.1021/jo401264w
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H15 N5 O3, C H Cl3'
_chemical_formula_sum            'C21 H16 Cl3 N5 O3'
_chemical_formula_weight         492.74
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-04-19T14:49:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.339(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3682(13)
_cell_length_b                   20.310(5)
_cell_length_c                   10.8183(13)
_cell_measurement_reflns_used    1600
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_measurement_wavelength     0.71073
_cell_volume                     2216.6(7)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.01
_diffrn_orient_matrix_UB_12      0
_diffrn_orient_matrix_UB_13      0
_diffrn_orient_matrix_UB_21      0
_diffrn_orient_matrix_UB_22      0.01
_diffrn_orient_matrix_UB_23      0
_diffrn_orient_matrix_UB_31      0
_diffrn_orient_matrix_UB_32      0
_diffrn_orient_matrix_UB_33      0.01
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_av_unetI/netI     0.1507
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            23410
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.219
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.266
_refine_ls_R_factor_all          0.179
_refine_ls_R_factor_gt           0.085
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc
 [0.00000+1.00000exp(3.00(sin\q/\l)^2^)]/
   [\s^2^(Fo^2^)+0.0400+0.0000*P+(0.1547P)^2^+0.0000sin\q/\l]
 where P = 0.10000Fo^2^ + 0.90000Fc^2^
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2324
_refine_ls_wR_factor_ref         0.2856
_reflns_number_gt                1893
_reflns_number_total             4035
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo401264w_si_002.cif
_cod_data_source_block           5a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028595