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_7063002
_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         'C54 H45 Cu2 I2 P3'
_chemical_formula_sum            'C54 H45 Cu2 I2 P3'
_chemical_formula_weight         1167.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_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                 105.593(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3589(4)
_cell_length_b                   20.5853(7)
_cell_length_c                   11.7439(6)
_cell_measurement_reflns_used    11749
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      35.1840
_cell_measurement_theta_min      3.2170
_cell_volume                     2412.11(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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_temperature      100.00
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details
;
  1 omega  -76.00  -47.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.2878  126.0000  -40.0000 29

  2 omega  -93.00  -67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.2878  -19.0000   90.0000 26

  3 omega  -36.00   -9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.2878  -19.0000   90.0000 27

  4 omega   41.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.3816  178.0000  -30.0000 67

  5 omega   -8.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.3816   19.0000   30.0000 115

  6 omega   32.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.3816  -99.0000  -90.0000 45

  7 omega   71.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.3816  178.0000   90.0000 32

  8 omega  -99.00  -23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.2468  -57.0000 -120.0000 76

  9 omega -107.00  -57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.2468 -178.0000   60.0000 50

 10 omega  -34.00   -9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.2468  -77.0000 -120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36890
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.532
_diffrn_reflns_theta_min         2.676
_exptl_absorpt_coefficient_mu    2.297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            cooourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_description       plate
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.323
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details
;
 Flack x determined using 5954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         19480
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0179P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.859
_reflns_Friedel_fraction_max     0.700
_reflns_number_gt                16801
_reflns_number_total             19480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03823h3.cif
_cod_data_source_block           kmd004c54cu2i2p3
_cod_depositor_comments
'Adding full bibliography for 7062994--7063002.cif.'
_cod_database_code               7063002
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C44(H44), C38(H38), C52(H52), C32(H32), C30(H30), C10(H10),
 C42(H42), C11(H11), C29(H29), C53(H53), C54(H54), C26(H26), C39(H39), C8(H8),
 C51(H51), C50(H50), C22(H22), C48(H48), C46(H46), C12(H12), C18(H18), C14(H14),
  C9(H9), C45(H45), C28(H28), C33(H33), C41(H41), C40(H40), C6(H6), C15(H15),
 C36(H36), C23(H23), C24(H24), C21(H21), C2(H2), C16(H16), C34(H34), C27(H27),
 C17(H17), C35(H35), C3(H3), C47(H47), C5(H5), C4(H4)
;
_shelx_res_checksum              10817
_olex2_submission_special_instructions 'No special instructions were received'