Efficient synthesis of N-2-aryl-1,2,3-triazole fluorophores via post-triazole arylation.
Liu, Yuxiu; Yan, Wuming; Chen, Yunfeng; Petersen, Jeffrey L.; Shi, Xiaodong; Organic letters 10 (2008) 5389–5392; doi:10.1021/ol802246q

data_1504963
_publ_section_title
;
 Efficient synthesis of N-2-aryl-1,2,3-triazole fluorophores via
 post-triazole arylation.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5389
_journal_page_last               5392
_journal_paper_doi               10.1021/ol802246q
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C14 H9 N5 O4'
_chemical_formula_weight         311.26
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.155(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7484(10)
_cell_length_b                   5.8038(5)
_cell_length_c                   17.2869(14)
_cell_measurement_reflns_used    7555
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.78
_cell_volume                     1379.37(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0667
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8539
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.18
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.9(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5756
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0734P)^2^+0.2237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1583
_reflns_number_gt                4775
_reflns_number_total             5756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802246q_si_007.cif
_cod_data_source_block           ms67ccd
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1504963