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_7061612
_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         'C14 H22 N2 O3'
_chemical_formula_sum            'C14 H22 N2 O3'
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_atom_sites_solution_secondary   difmap
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_audit_update_record
;
2022-04-07 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;
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_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
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_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
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_diffrn_ambient_temperature      293(2)
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_diffrn_reflns_av_unetI/netI     0.1297
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_diffrn_reflns_limit_l_min       -6
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_diffrn_reflns_theta_min         3.147
_diffrn_source                   'micro-focus sealed X-ray tube'
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_exptl_absorpt_correction_T_max  1.00000
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_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    1.135
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_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.0(10)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     157
_refine_ls_restrained_S_all      1.342
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.1419
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3939
_refine_ls_wR_factor_ref         0.4401
_reflns_Friedel_coverage         0.466
_reflns_Friedel_fraction_full    0.456
_reflns_Friedel_fraction_max     0.431
_reflns_number_gt                1206
_reflns_number_total             2043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02587f3.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7061606--7061612.cif.'
_cod_original_cell_volume        1168.5(5)
_cod_database_code               7061612
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              87773