Cu-catalyzed cycloaddition of aryl azides to 1-iodobuta-1,3-diynes: an experimental and quantum chemical study of unusual regiochemistry
Govdi, Anastasia I.; Danilkina, Natalia A.; Shtyrov, Andrey A.; Ryazantsev, Mikhail N.; Kim, Mia D.; Kryukova, Mariya A.; Balova, Irina A.; New Journal of Chemistry 48 (2024) 4831–4845; doi:10.1039/D3NJ03823H

data_7062996
_publ_section_title
;
 Cu-catalyzed cycloaddition of aryl azides to 1-iodobuta-1,3-diynes: an
 experimental and quantum chemical study of unusual regiochemistry
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4831
_journal_page_last               4845
_journal_paper_doi               10.1039/D3NJ03823H
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C19 H14 I N3 O'
_chemical_formula_sum            'C19 H14 I N3 O'
_chemical_formula_weight         427.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-06
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-07 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.113(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5258(6)
_cell_length_b                   7.4296(3)
_cell_length_c                   15.9339(8)
_cell_measurement_reflns_used    3834
_cell_measurement_temperature    100(5)
_cell_measurement_theta_max      71.7430
_cell_measurement_theta_min      3.1190
_cell_volume                     1643.47(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -18.00  16.00   0.50    0.20    --  -41.22 104.00 151.00   68
  2  \w    -75.00 -26.00   0.50    0.20    --  -41.22 104.00 151.00   98
  3  \w     50.00 109.00   0.50    0.20    --  101.00-104.00  49.00  118
  4  \w     82.00 154.00   0.50    0.20    --  101.00 104.00 151.00  144
  5  \w    -47.00   3.00   0.50    0.20    --  -41.22  32.00-120.00  100
  6  \w     26.00  53.00   0.50    0.20    --   41.22  54.00  60.00   54
  7  \w     20.00  68.00   0.50    0.20    --   41.22-104.00  49.00   96
  8  \w     77.00 102.00   0.50    0.20    --   41.22  21.00  60.00   50
  9  \w    -24.00   3.00   0.50    0.20    --   41.22 -32.00  60.00   54
 10  \w     63.00 104.00   0.50    0.20    --   41.22  54.00  60.00   82
 11  \w     24.00  55.00   0.50    0.20    --   41.22 -54.00  90.00   62
 12  \w     61.00  88.00   0.50    0.20    --   41.22  32.00 -90.00   54
 13  \w     23.00  50.00   0.50    0.20    --   41.22 -32.00  60.00   54
 14  \w    -15.00  21.00   0.50    0.20    --   41.22 -54.00  90.00   72
 15  \w     32.00  62.00   0.50    0.20    --   41.22  21.00  60.00   60
 16  \w     31.00  58.00   0.50    0.20    --   41.22 -77.00 -30.00   54
 17  \w     32.00 104.00   0.50    0.20    --   41.22  54.00 -90.00  144
 18  \w     47.00  94.00   0.50    0.20    --   41.22  32.00   0.00   94
 19  \w     46.00  71.00   0.50    0.20    --  101.00 -33.00 -30.00   50
 20  \w     54.00 110.00   0.50    0.20    --  101.00-111.00-150.00  112
 21  \w     41.00 114.00   0.50    0.20    --  101.00-111.00-120.00  146
 22  \w    129.00 157.00   0.50    0.20    --  101.00  17.00-150.00   56
 23  \w     51.00 109.00   0.50    0.20    --  101.00 -25.00 -30.00  116
 24  \w     40.00 107.00   0.50    0.20    --  101.00 -50.00  30.00  134
 25  \w     93.00 118.00   0.50    0.20    --  101.00  17.00-150.00   50
 26  \w     39.00 113.00   0.50    0.20    --  101.00 -68.00-150.00  148
 27  \w     81.00 151.00   0.50    0.20    --  101.00 111.00 -60.00  140
 28  \w     39.00  85.00   0.50    0.20    --  101.00 -33.00-120.00   92
 29  \w     84.00 112.00   0.50    0.20    --  101.00  93.00-120.00   56
 30  \w     36.00 122.00   0.50    0.20    --  101.00 -87.00  60.00  172
 31  \w     72.00 156.00   0.50    0.20    --  101.00   8.00 150.00  168
 32  \w    114.00 151.00   0.50    0.20    --  101.00 111.00  90.00   74
 33  \w     87.00 112.00   0.50    0.20    --  101.00-104.00  49.00   50
 34  \w    -46.00  -8.00   0.50    0.20    --  -41.22  43.00 120.00   76
 35  \w    -64.00 -28.00   0.50    0.20    --  -41.22 -43.00  90.00   72
 36  \w    -18.00  10.00   0.50    0.20    --   41.22 -43.00-180.00   56
 37  \w    -12.00   3.00   0.50    0.20    --   41.22-104.00 -60.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0058660000
_diffrn_orient_matrix_UB_12      -0.0368169000
_diffrn_orient_matrix_UB_13      0.0965781000
_diffrn_orient_matrix_UB_21      -0.0291499000
_diffrn_orient_matrix_UB_22      0.1964941000
_diffrn_orient_matrix_UB_23      0.0100952000
_diffrn_orient_matrix_UB_31      -0.1068184000
_diffrn_orient_matrix_UB_32      -0.0557212000
_diffrn_orient_matrix_UB_33      -0.0282858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8335
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        62.999
_diffrn_reflns_theta_max         62.999
_diffrn_reflns_theta_min         3.183
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.392
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.366
_refine_diff_density_min         -2.540
_refine_diff_density_rms         0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0633
_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^)+(0.1374P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2403
_reflns_number_total             2662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03823h3.cif
_cod_data_source_block           5699-10169_gai-866-3
_cod_depositor_comments
'Adding full bibliography for 7062994--7063002.cif.'
_cod_database_code               7062996
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H14 I N3 O'
_shelx_estimated_absorpt_t_max   0.282
_shelx_estimated_absorpt_t_min   0.126
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C14(H14), C17(H17), C16(H16), C13(H13), C6(H6), C7(H7)
1.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              34477
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.632
_oxdiff_exptl_absorpt_empirical_full_min 0.565