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_7062998
_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 Cu I P3, C2 H3 N'
_chemical_formula_sum            'C56 H48 Cu I N P3'
_chemical_formula_weight         1018.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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            4
_cell_length_a                   18.5498(2)
_cell_length_b                   20.2300(2)
_cell_length_c                   12.7711(2)
_cell_measurement_reflns_used    21072
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.5460
_cell_measurement_theta_min      2.7960
_cell_volume                     4792.51(10)
_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
;
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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details
;
  1 omega  -52.00   27.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.2658   57.0000  120.0000 79

  2 omega   -1.00   38.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.2658   57.0000  -30.0000 39

  3 omega  -40.00   37.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.2658   57.0000 -150.0000 77

  4 omega   14.00   39.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.2658   77.0000    0.0000 25

  5 omega   40.00   67.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3596   77.0000   90.0000 27

  6 omega   33.00   90.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3596   77.0000  -90.0000 57

  7 omega    4.00   33.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3596   77.0000   90.0000 29
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0193276000
_diffrn_orient_matrix_UB_12      0.0224081000
_diffrn_orient_matrix_UB_13      -0.0322194000
_diffrn_orient_matrix_UB_21      -0.0226684000
_diffrn_orient_matrix_UB_22      -0.0261302000
_diffrn_orient_matrix_UB_23      -0.0168664000
_diffrn_orient_matrix_UB_31      -0.0239536000
_diffrn_orient_matrix_UB_32      0.0066837000
_diffrn_orient_matrix_UB_33      0.0419916000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            44915
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.888
_diffrn_reflns_theta_min         2.714
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96457
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       plate
_exptl_crystal_F_000             2072
_exptl_crystal_preparation       plate
_exptl_crystal_recrystallization_method plate
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 6058 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         17488
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0189P)^2^+0.7176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0537
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.725
_reflns_number_gt                15831
_reflns_number_total             17488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03823h3.cif
_cod_data_source_block           15397_dna_120fl
_cod_depositor_comments
'Adding full bibliography for 7062994--7063002.cif.'
_cod_original_cell_volume        4792.52(10)
_cod_database_code               7062998
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C54 H45 Cu2 I2 P3'
_shelx_estimated_absorpt_t_max   0.827
_shelx_estimated_absorpt_t_min   0.772
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C44(H44), C3(H3), C36(H36), C2(H2), C20(H20), C27(H27), C38(H38), C10(H10),
 C8(H8), C54(H54), C17(H17), C50(H50), C12(H12), C35(H35), C4(H4), C53(H53),
 C26(H26), C34(H34), C42(H42), C28(H28), C48(H48), C14(H14), C51(H51), C45(H45),
  C24(H24), C30(H30), C9(H9), C52(H52), C11(H11), C46(H46), C29(H29), C18(H18),
 C6(H6), C41(H41), C5(H5), C47(H47), C39(H39), C21(H21), C40(H40), C32(H32),
 C22(H22), C15(H15), C33(H33), C16(H16), C23(H23)
1.b Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC)
;
_shelx_res_checksum              94111
_olex2_date_sample_data_collection 2020-01-30
_olex2_exptl_crystal_mounting_method plate
_olex2_submission_special_instructions 'No special instructions were received'