Conversion of 3-amino-4-arylamino-1<i>H</i>-isochromen-1-ones to 1-arylisochromeno[3,4-<i>d</i>][1,2,3]triazol-5(1<i>H</i>)-ones: synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative
Vicentes, Daniel E.; Romero, Andrea L.; Rodríguez, Ricuarte; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 76 (2020) 446–453; doi:10.1107/S2053229620003757

data_2022145
_publ_section_title
;
 Conversion of 3-amino-4-arylamino-1<i>H</i>-isochromen-1-ones to
 1-arylisochromeno[3,4-<i>d</i>][1,2,3]triazol-5(1<i>H</i>)-ones:
 synthesis, spectroscopic characterization and the structures of four
 products and one ring-opened derivative
;
_journal_coeditor_code           SK3747
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              446
_journal_page_last               453
_journal_paper_doi               10.1107/S2053229620003757
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C16 H11 N3 O2'
_chemical_formula_moiety         'C16 H11 N3 O2'
_chemical_formula_sum            'C16 H11 N3 O2'
_chemical_formula_weight         277.28
_chemical_name_systematic
;
1-(2-Methylphenyl)isochromeno[3,4-<i>d</i>][1,2,3]triazol-5(1<i>H</i>)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 112.957(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5676(5)
_cell_length_b                   20.2663(14)
_cell_length_c                   9.2503(7)
_cell_measurement_reflns_used    3244
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.340
_cell_measurement_theta_min      2.594
_cell_volume                     1306.33(16)
_computing_cell_refinement
;
APEX3 (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
APEX3 (Bruker, 2018)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            36209
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.340
_diffrn_reflns_theta_min         2.594
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.6412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                2915
_reflns_number_total             3242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3747sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022145
_cod_database_fobs_code          2022145
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.985
_shelx_hkl_checksum              14386
_shelx_res_checksum              91507
_shelxl_version_number           2.014