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_7061611
_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_absolute_configuration rm
_chemical_formula_moiety         'C20 H27 N5 O4'
_chemical_formula_sum            'C20 H27 N5 O4'
_chemical_formula_weight         401.47
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_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_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
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_cell_angle_gamma                90
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_cell_length_b                   10.6927(5)
_cell_length_c                   24.4593(12)
_cell_measurement_reflns_used    3911
_cell_measurement_temperature    204(2)
_cell_measurement_theta_max      75.5570
_cell_measurement_theta_min      3.5200
_cell_volume                     2056.38(17)
_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      204(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.994
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_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6469
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.594
_diffrn_reflns_theta_min         3.614
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94149
_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    1.297
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1285 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.19(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0813P)^2^+0.5035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1415
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    0.857
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                3651
_reflns_number_total             3885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02587f3.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7061606--7061612.cif.'
_cod_database_code               7061611
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              95316