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_7063001
_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 O2'
_chemical_formula_sum            'C19 H14 I N3 O2'
_chemical_formula_weight         443.23
_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                 97.8050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.40890(10)
_cell_length_b                   8.48620(10)
_cell_length_c                   19.6955(3)
_cell_measurement_reflns_used    19123
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9540
_cell_measurement_theta_min      4.2970
_cell_volume                     1723.63(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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    -28.00  23.00   0.50    0.05    --  -47.20  42.00 -55.00  102
  2  \w    -24.00  28.00   0.50    0.05    --  -47.20  19.00  90.00  104
  3  \w     51.00  96.00   0.50    0.05    --   47.20  42.00 -55.00   90
  4  \w    149.00 174.00   0.50    0.12    --  107.75  42.00 -55.00   50
  5  \w    106.00 178.00   0.50    0.12    --  107.75  30.00   0.00  144
  6  \w    100.00 126.00   0.50    0.12    --  107.75  42.00 -55.00   52
  7  \w    102.00 158.00   0.50    0.12    --  107.75  30.00  60.00  112
  8  \w     63.00 102.00   0.50    0.12    --  107.75 -94.00 -60.00   78
  9  \w     58.00 106.00   0.50    0.12    --  107.75 -77.00 -30.00   96
 10  \w     36.00  69.00   0.50    0.12    --  107.75 -61.00   0.00   66
 11  \w     45.00  93.00   0.50    0.12    --  107.75 -77.00  30.00   96
 12  \w     60.00  89.00   0.50    0.12    --  107.75-125.00  90.00   58
 13  \w     40.00  69.00   0.50    0.12    --  107.75 -61.00 150.00   58
 14  \w     37.00  70.00   0.50    0.12    --  107.75 -61.00  60.00   66
 15  \w     37.00  82.00   0.50    0.12    --  107.75 -94.00 -30.00   90
 16  \w     40.00  66.00   0.50    0.12    --  107.75 -61.00 -60.00   52
 17  \w     43.00  70.00   0.50    0.12    --  107.75 -61.00 -30.00   54
 18  \w     35.00 100.00   0.50    0.12    --  107.75 -77.00-120.00  130
 19  \w     35.00  60.00   0.50    0.12    --  107.75 -61.00-150.00   50
 20  \w     35.00 103.00   0.50    0.12    --  107.75 -94.00-150.00  136
 21  \w      8.00  33.00   0.50    0.05    --   47.20 -42.00 152.00   50
 22  \w    -99.00 -37.00   0.50    0.05    --  -47.20 -42.00 152.00  124
 23  \w   -125.00 -83.00   0.50    0.12    -- -106.00 -94.00  90.00   84
 24  \w   -166.00-140.00   0.50    0.12    -- -106.00 -15.00  30.00   52
 25  \w   -172.00-147.00   0.50    0.12    -- -106.00 -94.00  90.00   50
 26  \w   -176.00 -95.00   0.50    0.12    -- -106.00 -42.00 152.00  162
 27  \w    -64.00 -33.00   0.50    0.12    -- -106.00  61.00 -60.00   62
 28  \w    -70.00 -34.00   0.50    0.12    -- -106.00  61.00 -90.00   72
 29  \w    -71.00 -46.00   0.50    0.12    -- -106.00  61.00-180.00   50
 30  \w   -120.00 -74.00   0.50    0.05    --  -47.20-125.00-120.00   92
 31  \w     -5.00  36.00   0.50    0.05    --   47.20 -42.00 152.00   82
 32  \w    -24.00   8.00   0.50    0.05    --  -47.20  19.00 -60.00   64
 33  \w     35.00  62.00   0.50    0.05    --   47.20  57.00  90.00   54
 34  \w     30.00  94.00   0.50    0.05    --   47.20  77.00   0.00  128
 35  \w     67.00  93.00   0.50    0.05    --   47.20  57.00  90.00   52
 36  \w   -123.00 -92.00   0.50    0.12    -- -106.00 -54.00  32.12   62
 37  \w   -165.00-139.00   0.50    0.12    -- -106.00 -45.00  90.00   52
 38  \w   -109.00 -83.00   0.50    0.12    -- -106.00 -80.00  80.16   52
 39  \w   -121.00 -90.00   0.50    0.12    -- -106.00 -68.00  30.02   62
 40  \w   -114.00 -88.00   0.50    0.12    -- -106.00 -66.00  36.09   52
 41  \w   -108.00 -83.00   0.50    0.12    -- -106.00 -80.00  48.79   50
 42  \w   -118.00 -85.00   0.50    0.12    -- -106.00 -77.00  90.00   66
 43  \w   -108.00 -83.00   0.50    0.12    -- -106.00 -77.00 120.00   50
 44  \w   -169.00-124.00   0.50    0.12    -- -106.00 -64.00  86.65   90
 45  \w   -138.00 -93.00   0.50    0.12    -- -106.00 -45.00  90.00   90
 46  \w   -113.00 -87.00   0.50    0.12    -- -106.00 -69.00  57.93   52
 47  \w   -176.00-150.00   0.50    0.12    -- -106.00 -45.00 120.00   52
 48  \w   -166.00-140.00   0.50    0.12    -- -106.00 -55.00 111.02   52
 49  \w   -152.00 -85.00   0.50    0.12    -- -106.00 -72.00  99.39  134
 50  \w   -125.00 -99.00   0.50    0.12    -- -106.00 -45.00 120.00   52
 51  \w   -128.00 -85.00   0.50    0.12    -- -106.00 -72.00  16.91   86
 52  \w    -64.00 -38.00   0.50    0.12    -- -106.00  61.00 150.00   52
 53  \w   -110.00 -85.00   0.50    0.12    -- -106.00 -77.00  60.00   50
 54  \w   -105.00 -80.00   0.50    0.12    -- -106.00 -84.00 109.59   50
 55  \w   -126.00 -94.00   0.50    0.12    -- -106.00 -55.00 111.02   64
 56  \w   -107.00 -82.00   0.50    0.12    -- -106.00 -79.00  71.91   50
 57  \w    -71.00 -46.00   0.50    0.12    -- -106.00  61.00  90.00   50
 58  \w   -106.00 -81.00   0.50    0.12    -- -106.00 -83.00  87.99   50
 59  \w   -177.00-149.00   0.50    0.12    -- -106.00 -69.00  22.39   56
 60  \w   -139.00 -86.00   0.50    0.12    -- -106.00 -69.00  22.39  106
 61  \w    -70.00 -33.00   0.50    0.12    -- -106.00  61.00-150.00   74
 62  \w   -117.00 -92.00   0.50    0.12    -- -106.00 -64.00  86.65   50
 63  \w   -107.00 -82.00   0.50    0.12    -- -106.00 -79.00  64.30   50
 64  \w   -120.00 -95.00   0.50    0.12    -- -106.00 -61.00  30.00   50
 65  \w   -112.00 -87.00   0.50    0.12    -- -106.00 -67.00  23.36   50
 66  \w   -116.00 -91.00   0.50    0.12    -- -106.00 -60.00  76.27   50
 67  \w   -113.00 -88.00   0.50    0.12    -- -106.00 -69.00  43.75   50
 68  \w     80.00 106.00   0.50    0.12    --  107.75 -94.00 120.00   52
 69  \w    124.00 167.00   0.50    0.12    --  107.75  61.00-150.00   86
 70  \w    124.00 178.00   0.50    0.12    --  107.75  88.00  62.58  108
 71  \w     81.00 107.00   0.50    0.12    --  107.75  88.00  62.58   52
 72  \w    108.00 144.00   0.50    0.12    --  107.75  61.00   0.00   72
 73  \w     91.00 117.00   0.50    0.12    --  107.75  61.00  30.00   52
 74  \w     71.00  99.00   0.50    0.12    --  107.75 -94.00-120.00   56
 75  \w     80.00 106.00   0.50    0.12    --  107.75 -94.00 150.00   52
 76  \w     85.00 112.00   0.50    0.12    --  107.75  77.00  60.00   54
 77  \w     41.00  67.00   0.50    0.12    --  107.75 -94.00-120.00   52
 78  \w    125.00 177.00   0.50    0.12    --  107.75  61.00  90.00  104
 79  \w    127.00 178.00   0.50    0.12    --  107.75  61.00-180.00  102
 80  \w     35.00  75.00   0.50    0.12    --  107.75 -77.00  60.00   80
 81  \w     36.00  72.00   0.50    0.12    --  107.75 -94.00 150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0998637000
_diffrn_orient_matrix_UB_12      0.0622583000
_diffrn_orient_matrix_UB_13      0.0445265000
_diffrn_orient_matrix_UB_21      0.1106546000
_diffrn_orient_matrix_UB_22      0.0718080000
_diffrn_orient_matrix_UB_23      0.0504593000
_diffrn_orient_matrix_UB_31      -0.0112444000
_diffrn_orient_matrix_UB_32      0.1546377000
_diffrn_orient_matrix_UB_33      -0.0412151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33076
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.438
_diffrn_reflns_theta_min         4.287
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
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    1.708
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+1.4960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0652
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3536
_reflns_number_total             3618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03823h3.cif
_cod_data_source_block           16779_gai-982-1_2
_cod_depositor_comments
'Adding full bibliography for 7062994--7063002.cif.'
_cod_database_code               7063001
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H14 I1 N3 O2'
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C6(H6), C13(H13), C7(H7), C9(H9), C16(H16), C10(H10)
1.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              49874
_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 1.885
_oxdiff_exptl_absorpt_empirical_full_min 0.723