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_4028596
_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         'C22 H19 N3 O2, C3 H6 O'
_chemical_formula_sum            'C25 H25 N3 O3'
_chemical_formula_weight         415.48
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_symmetry_space_group_name_Hall  '-P 2yn'
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_cell_length_b                   8.812(2)
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_cell_measurement_temperature    200(2)
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_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
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_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'
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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
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_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
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_diffrn_reflns_limit_h_min       -19
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_diffrn_reflns_limit_l_min       0
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_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         27.51
_diffrn_reflns_theta_min         3.01
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.018
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            'slight red'
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
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_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4948
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_refine_ls_restrained_S_all      0.941
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_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.149
_reflns_number_gt                2298
_reflns_number_total             4948
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo401264w_si_003.cif
_cod_data_source_block           6b
_cod_original_cell_volume        2159.6(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4028596