Metal-free cycloaddition to synthesize naphtho[2,3-d][1,2,3]triazole-4,9-diones.
Chen, Ping-Fan; Kuo, Kung-Kai; Vandavasi, Jaya Kishore; Boominathan, Siva Senthil Kumar; Chen, Chung-Yu; Wang, Jeh-Jeng; Organic & biomolecular chemistry 13 (2015) 9261–9266; doi:10.1039/c5ob01322d

data_7154609
_publ_section_title
;
 Metal-free cycloaddition to synthesize
 naphtho[2,3-d][1,2,3]triazole-4,9-diones.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9261
_journal_page_last               9266
_journal_paper_doi               10.1039/c5ob01322d
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C16 H9 N3 O2'
_chemical_formula_sum            'C16 H9 N3 O2'
_chemical_formula_weight         275.26
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-29 deposited with the CCDC.
2015-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.275(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.897(17)
_cell_length_b                   6.420(5)
_cell_length_c                   8.292(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1266.8(16)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0740
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2966
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9339
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1559
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0564P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                1093
_reflns_number_total             1559
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01322d2.cif
_cod_data_source_block           ch15378
_cod_depositor_comments
'Adding full bibliography for 7154608--7154609.cif.'
_cod_original_cell_volume        1266.6(16)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7154609