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_7062995
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   4.7694(2)
_cell_length_b                   20.4826(12)
_cell_length_c                   35.0406(16)
_cell_measurement_reflns_used    7726
_cell_measurement_temperature    100(6)
_cell_measurement_theta_max      71.5050
_cell_measurement_theta_min      2.4580
_cell_volume                     3423.1(3)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_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    -57.00  21.00   0.50    0.65    --  -41.35  54.00-109.00  156
  2  \w    -53.00 -25.00   0.50    0.65    --  -41.35 -54.00 106.00   56
  3  \w   -100.00 -74.00   0.50    0.65    --  -41.35 -54.00 106.00   52
  4  \w     64.00  89.00   0.50    0.65    --   41.35  54.00-109.00   50
  5  \w     52.00 119.00   0.50    2.61    --  101.00 -54.00 106.00  134
  6  \w     89.00 135.00   0.50    2.61    --  101.00  54.00-109.00   92
  7  \w    -47.00  14.00   0.50    0.65    --  -41.35  32.00-120.00  122
  8  \w   -107.00 -37.00   0.50    0.65    --  -41.35 -32.00 -90.00  140
  9  \w     -4.00  21.00   0.50    0.65    --  -41.35  43.00  60.00   50
 10  \w    -51.00  -6.00   0.50    0.65    --  -41.35  54.00  60.00   90
 11  \w    -52.00 -16.00   0.50    0.65    --  -41.35  43.00  60.00   72
 12  \w     16.00  64.00   0.50    0.65    --   41.35 -11.00 120.00   96
 13  \w     40.00 100.00   0.50    0.65    --   41.35  32.00  90.00  120
 14  \w     41.00  70.00   0.50    0.65    --   41.35  77.00 120.00   58
 15  \w     -9.00  34.00   0.50    0.65    --   41.35 -54.00 106.00   86
 16  \w    -31.00   9.00   0.50    0.65    --   41.35 -11.00 120.00   80
 17  \w    -21.00  48.00   0.50    0.65    --   41.35 -32.00 -60.00  138
 18  \w     80.00 105.00   0.50    0.65    --   41.35  77.00 120.00   50
 19  \w    107.00 138.00   0.50    2.61    --  101.00  17.00  30.00   62
 20  \w     37.00 100.00   0.50    2.61    --  101.00 178.00 120.00  126
 21  \w    120.00 146.00   0.50    2.61    --  101.00  59.00 120.00   52
 22  \w     44.00 114.00   0.50    2.61    --  101.00 -42.00-180.00  140
 23  \w     36.00  91.00   0.50    2.61    --  101.00 -33.00  60.00  110
 24  \w    117.00 155.00   0.50    2.61    --  101.00  33.00-150.00   76
 25  \w     94.00 147.00   0.50    2.61    --  101.00  33.00-180.00  106
 26  \w     92.00 155.00   0.50    2.61    --  101.00  33.00 -30.00  126
 27  \w     91.00 137.00   0.50    2.61    --  101.00  50.00-150.00   92
 28  \w     66.00  97.00   0.50    2.61    --  101.00 -68.00-120.00   62
 29  \w    130.00 157.00   0.50    2.61    --  101.00  33.00 -90.00   54
 30  \w     49.00 105.00   0.50    2.61    --  101.00 -59.00 -90.00  112
 31  \w     40.00  77.00   0.50    2.61    --  101.00 -25.00 -60.00   74
 32  \w     89.00 115.00   0.50    2.61    --  101.00  59.00-180.00   52
 33  \w     94.00 149.00   0.50    2.61    --  101.00  33.00 -60.00  110
 34  \w     63.00 108.00   0.50    2.61    --  101.00 -33.00-120.00   90
 35  \w    -43.00 -18.00   0.50    0.65    --  -41.35  54.00-109.00   50
 36  \w    -59.00 -33.00   0.50    0.65    --  -41.35 -32.00 -90.00   52
 37  \w    -97.00 -60.00   0.50    0.65    --  -41.35 138.00  60.00   74
 38  \w    -33.00   3.00   0.50    0.65    --  -41.35  43.00 120.00   72
 39  \w     47.00  73.00   0.50    0.65    --   41.35  54.00  30.00   52
 40  \w     79.00 104.00   0.50    0.65    --   41.35  32.00   0.00   50
 41  \w     22.00  73.00   0.50    0.65    --   41.35  65.00   0.00  102
 42  \w     48.00  74.00   0.50    0.65    --   41.35  32.00   0.00   52
 43  \w     14.00  40.00   0.50    0.65    --   41.35 -32.00-120.00   52
 44  \w     29.00  67.00   0.50    0.65    --   41.35  65.00  30.00   76
 45  \w     77.00 103.00   0.50    0.65    --   41.35  32.00 120.00   52
 46  \w     80.00 113.50   0.50    2.61    --  101.00  68.00   0.00   67
;
_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      0.2102510000
_diffrn_orient_matrix_UB_12      0.0155378000
_diffrn_orient_matrix_UB_13      -0.0320436000
_diffrn_orient_matrix_UB_21      -0.0041321000
_diffrn_orient_matrix_UB_22      0.0726312000
_diffrn_orient_matrix_UB_23      0.0115067000
_diffrn_orient_matrix_UB_31      0.2451408000
_diffrn_orient_matrix_UB_32      -0.0120303000
_diffrn_orient_matrix_UB_33      0.0278025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            21545
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.648
_diffrn_reflns_theta_min         2.522
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40682
_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    1.658
_exptl_crystal_description       needle
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.982
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0494P)^2^+16.1594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2880
_reflns_number_total             3352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03823h3.cif
_cod_data_source_block           5699-10169_gai-866-1
_cod_depositor_comments
'Adding full bibliography for 7062994--7063002.cif.'
_cod_database_code               7062995
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H14 I N3 O'
_shelx_estimated_absorpt_t_max   0.320
_shelx_estimated_absorpt_t_min   0.067
_olex2_refinement_description
;
1. Others
 Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(H14A)=Sof(O2A)=1-FVAR(1)
 Sof(O1A)=Sof(C16)=Sof(H16)=Sof(C13)=Sof(H13)=Sof(C17)=Sof(H17)=Sof(C14)=
 Sof(H14)=FVAR(1)
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C5(H5), C6(H6), C16(H16), C13(H13), C17(H17), C16A(H16A),
 C17A(H17A), C13A(H13A), C14(H14), C14A(H14A)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              27742
_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 2.388
_oxdiff_exptl_absorpt_empirical_full_min 0.377