Synthesis of 3,3-disubstituted-2,3-dihydroazanaphthoquinones via simultaneous alkyne oxidation and nitrile hydration of ortho-alkynylarenenitriles.
Sakthivel, Karuppusamy; Srinivasan, Kannupal; Organic & biomolecular chemistry 12 (2014) 6440–6446; doi:10.1039/c4ob00852a

data_7153939
_publ_section_title
;
 Synthesis of 3,3-disubstituted-2,3-dihydroazanaphthoquinones via
 simultaneous alkyne oxidation and nitrile hydration of
 ortho-alkynylarenenitriles.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6440
_journal_page_last               6446
_journal_paper_doi               10.1039/c4ob00852a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C25 H21 N O4'
_chemical_formula_weight         399.43
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.955(6)
_cell_angle_beta                 96.292(5)
_cell_angle_gamma                96.603(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4396(6)
_cell_length_b                   10.7479(7)
_cell_length_c                   11.8458(7)
_cell_measurement_temperature    293(2)
_cell_volume                     1020.31(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.859
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11252
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         3.88
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0555P)^2^+0.0049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                2673
_reflns_number_total             4730
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00852a2.cif
_cod_data_source_block           cs-sr-1
_cod_depositor_comments          'Adding full bibliography for 7153939.cif.'
_cod_database_code               7153939