Synthesis of 1,2,3-triazole-fused N-heterocycles from <i>N</i>-alkynyl hydroxyisoindolinones and sodium azide <i>via</i> the Huisgen reaction.
Arandhara, Pallav Jyoti; Behera, Bipin Kumar; Biswas, Subhamoy; Saikia, Anil K.; Organic & biomolecular chemistry 21 (2023) 8772–8781; doi:10.1039/d3ob01498c

data_7159599
_publ_section_title
;
 Synthesis of 1,2,3-triazole-fused N-heterocycles from <i>N</i>-alkynyl
 hydroxyisoindolinones and sodium azide <i>via</i> the Huisgen reaction.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8772
_journal_page_last               8781
_journal_paper_doi               10.1039/d3ob01498c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration S
_chemical_formula_sum            'C12 H12 N4 O2'
_chemical_formula_weight         244.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-06-12 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.242(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0470(8)
_cell_length_b                   4.9832(4)
_cell_length_c                   11.8477(10)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.39
_cell_volume                     574.94(8)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18229
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.988
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         1.773
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.715
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2013
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.715
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.3040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1867
_reflns_number_total             2013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01498c2.cif
_cod_data_source_block           AKS_0m_a
_cod_depositor_comments          'Adding full bibliography for 7159599.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159599
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              25971