Tandem amide coupling and hydroamination: unexpected benzotriazole oxide addition to the propiolic acid triple bond
Opačak, Saša; Perić, Berislav; Gojšić, Tomislav; Čikoš, Ana; Vikić-Topić, Dražen; Kirin, Srećko I.; New Journal of Chemistry 46 (2022) 13275–13285; doi:10.1039/D2NJ02587F

data_7061609
_publ_section_title
;
 Tandem amide coupling and hydroamination: unexpected benzotriazole oxide
 addition to the propiolic acid triple bond
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13275
_journal_page_last               13285
_journal_paper_doi               10.1039/D2NJ02587F
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C8 H10 O5'
_chemical_formula_sum            'C8 H10 O5'
_chemical_formula_weight         186.16
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8849(7)
_cell_length_b                   30.166(4)
_cell_length_c                   7.806(4)
_cell_measurement_reflns_used    402
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.0630
_cell_measurement_theta_min      6.4720
_cell_volume                     898.6(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2359
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        62.428
_diffrn_reflns_theta_max         62.428
_diffrn_reflns_theta_min         2.930
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0959
_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^)+(0.1467P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2331
_refine_ls_wR_factor_ref         0.2928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                680
_reflns_number_total             1384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02587f3.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7061606--7061612.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7061609
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              47846