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_7154608
_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         'C20 H14 N6 O4'
_chemical_formula_sum            'C20 H14 N6 O4'
_chemical_formula_weight         402.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_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
_audit_update_record
;
2015-06-29 deposited with the CCDC.
2015-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                74.882(4)
_cell_angle_beta                 64.370(4)
_cell_angle_gamma                64.823(4)
_cell_formula_units_Z            10
_cell_length_a                   17.0052(7)
_cell_length_b                   17.3045(8)
_cell_length_c                   19.3461(8)
_cell_measurement_reflns_used    8431
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1749
_cell_measurement_theta_min      2.6685
_cell_volume                     4624.5(4)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39884
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         2.67
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1351
_refine_ls_number_reflns         21289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+1.3280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1183
_reflns_number_gt                14407
_reflns_number_total             21289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01322d2.cif
_cod_data_source_block           bn4ome
_cod_depositor_comments
'Adding full bibliography for 7154608--7154609.cif.'
_cod_original_cell_volume        4624.5(3)
_cod_database_code               7154608