1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: A One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles.
Govdi, Anastasia I.; Danilkina, Natalia A.; Ponomarev, Alexander V.; Balova, Irina A.; The Journal of organic chemistry 84 (2019) 1925–1940; doi:10.1021/acs.joc.8b02916

data_4033776
_publ_section_title
;
 1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: A
 One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1925
_journal_page_last               1940
_journal_paper_doi               10.1021/acs.joc.8b02916
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C26 H21 N5'
_chemical_formula_sum            'C26 H21 N5'
_chemical_formula_weight         403.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                88.792(2)
_cell_angle_beta                 80.674(2)
_cell_angle_gamma                78.623(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0850(2)
_cell_length_b                   9.7409(3)
_cell_length_c                   13.8853(3)
_cell_measurement_reflns_used    8150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.3660
_cell_measurement_theta_min      3.1690
_cell_volume                     1057.81(5)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -89.00 -64.00   0.50    0.20    --  -41.35 125.00 166.00   50
  2  \w   -102.00 -16.00   0.50    0.20    --  -41.35 146.00 -27.00  172
  3  \w     15.00  90.00   0.50    0.20    --   41.35-146.00 -78.00  150
  4  \w     53.00  79.00   0.50    0.20    --   41.35-125.00  87.00   52
  5  \w    103.00 130.00   0.50    0.55    --  100.29-146.00 -78.00   54
  6  \w    106.00 154.00   0.50    0.55    --  100.29 125.00 166.00   96
  7  \w     86.00 113.00   0.50    0.55    --  100.29-125.00  87.00   54
  8  \w     84.00 111.00   0.50    0.55    --  100.29 146.00 -27.00   54
  9  \w    -59.00   2.00   0.50    0.20    --  -41.35  65.00  30.00  122
 10  \w    -25.00  17.00   0.50    0.20    --  -41.35 104.00 -90.00   84
 11  \w   -107.00 -81.00   0.50    0.20    --  -41.35 -21.00  30.00   52
 12  \w    -28.00  -3.00   0.50    0.20    --  -41.35 125.00 166.00   50
 13  \w    -96.00 -63.00   0.50    0.20    --  -41.35 -54.00 120.00   66
 14  \w    -95.00 -63.00   0.50    0.20    --  -41.35 -54.00  60.00   64
 15  \w    -59.00 -24.00   0.50    0.20    --  -41.35 -54.00  60.00   70
 16  \w    -69.00 -36.00   0.50    0.20    --  -41.35 104.00 -90.00   66
 17  \w    -80.00 -34.00   0.50    0.20    --  -41.35 -21.00  30.00   92
 18  \w    -91.00 -66.00   0.50    0.20    --  -41.35 -32.00-150.00   50
 19  \w    -60.00 -32.00   0.50    0.20    --  -41.35 -54.00 120.00   56
 20  \w     39.00  64.00   0.50    0.20    --   41.35  21.00-180.00   50
 21  \w     70.00 109.00   0.50    0.20    --   41.35  21.00-180.00   78
 22  \w     18.00  43.00   0.50    0.20    --   41.35 -43.00-180.00   50
 23  \w     27.00  54.00   0.50    0.20    --   41.35 -43.00  30.00   54
 24  \w     15.00  48.00   0.50    0.20    --   41.35 -32.00  90.00   66
 25  \w     35.00 104.00   0.50    0.20    --   41.35  32.00  30.00  138
 26  \w     70.00 103.00   0.50    0.20    --   41.35  54.00 -60.00   66
 27  \w     28.00  65.00   0.50    0.20    --   41.35  54.00 -60.00   74
 28  \w     33.00  97.00   0.50    0.55    --  100.29 -25.00 -90.00  128
 29  \w     89.00 119.00   0.50    0.55    --  100.29 -59.00 -90.00   60
 30  \w     86.00 126.00   0.50    0.55    --  100.29 -77.00-120.00   80
 31  \w     33.00  89.00   0.50    0.55    --  100.29 -25.00   0.00  112
 32  \w     39.00 113.00   0.50    0.55    --  100.29 -42.00 150.00  148
 33  \w     82.00 107.00   0.50    0.55    --  100.29 -87.00-180.00   50
 34  \w     50.00  88.00   0.50    0.55    --  100.29 -59.00 -90.00   76
 35  \w     40.00  67.00   0.50    0.55    --  100.29 -87.00-180.00   54
 36  \w     35.00 110.00   0.50    0.55    --  100.29 -33.00  60.00  150
 37  \w     45.00  81.00   0.50    0.55    --  100.29 -77.00-120.00   72
 38  \w     46.00 100.00   0.50    0.55    --  100.29 -33.00-120.00  108
 39  \w     85.00 136.00   0.50    0.55    --  100.29  96.00 120.00  102
 40  \w     89.00 155.00   0.50    0.55    --  100.29  42.00-150.00  132
 41  \w     71.00 106.00   0.50    0.55    --  100.29 -96.00  90.00   70
 42  \w     30.00  57.00   0.50    0.55    --  100.29 -96.00  90.00   54
 43  \w     73.00 117.00   0.50    0.55    --  100.29 -77.00 -30.00   88
 44  \w     35.00 109.00   0.50    0.55    --  100.29 -96.00 -60.00  148
 45  \w     84.00 115.00   0.50    0.55    --  100.29 -68.00  60.00   62
 46  \w    100.00 156.00   0.50    0.55    --  100.29  25.00 -90.00  112
 47  \w     79.00 126.00   0.50    0.55    --  100.29 -77.00 120.00   94
 48  \w     44.00  70.00   0.50    0.55    --  100.29 -77.00 120.00   52
 49  \w     85.00 132.00   0.50    0.55    --  100.29  96.00-150.00   94
 50  \w    100.00 130.00   0.50    0.55    --  100.29-145.00   0.00   60
 51  \w     41.00  67.00   0.50    0.55    --  100.29-145.00   0.00   52
 52  \w    103.00 157.00   0.50    0.55    --  100.29  25.00 120.00  108
 53  \w    105.00 149.00   0.50    0.55    --  100.29 117.00 150.00   88
 54  \w     87.00 115.00   0.50    0.55    --  100.29  42.00 -60.00   56
 55  \w     90.00 154.00   0.50    0.55    --  100.29  17.00-180.00  128
 56  \w     47.00  82.00   0.50    0.55    --  100.29 -68.00  60.00   70
 57  \w    104.00 131.00   0.50    0.55    --  100.29  50.00 -90.00   54
 58  \w     36.00  90.00   0.50    0.20    --   41.35  65.00 -90.00  108
 59  \w    -44.00 -19.00   0.50    0.20    --    0.00 119.00 149.84   50
 60  \w    -10.00  15.00   0.50    0.20    --   24.00 101.00 -10.27   50
 61  \w     -3.00  22.00   0.50    0.20    --   28.00  94.00 170.91   50
 62  \w     -1.00  24.00   0.50    0.20    --   28.00  90.00  84.35   50
 63  \w      3.00  28.00   0.50    0.20    --   32.00  90.00-124.07   50
 64  \w      2.00  27.00   0.50    0.20    --   32.00  91.00 -84.69   50
 65  \w      3.00  28.00   0.50    0.20    --   32.00  89.00  -3.23   50
 66  \w      9.00  34.00   0.50    0.20    --   36.00  84.00 -91.10   50
 67  \w      9.00  34.00   0.50    0.20    --   36.00  85.00-119.19   50
 68  \w     15.00  40.00   0.50    0.20    --   40.00  81.00 166.23   50
 69  \w     19.00  60.00   0.50    0.20    --   41.35 -65.00  60.00   82
 70  \w     30.00  55.00   0.50    0.20    --   41.35 -43.00-150.00   50
 71  \w     19.00  44.00   0.50    0.20    --   44.00  81.00  87.19   50
 72  \w     19.00  44.00   0.50    0.20    --   44.00  79.00-167.13   50
 73  \w     18.00  43.00   0.50    0.20    --   44.00  82.00  45.44   50
 74  \w     18.00  43.00   0.50    0.20    --   44.00  82.00 -47.34   50
 75  \w     18.00  43.00   0.50    0.20    --   44.00  82.00 113.77   50
 76  \w     19.00  44.00   0.50    0.20    --   44.00  81.00 -10.39   50
 77  \w     18.00  43.00   0.50    0.20    --   44.00  82.00  24.52   50
 78  \w     19.00  44.00   0.50    0.20    --   44.00  80.00-103.91   50
 79  \w     27.00  55.00   0.50    0.20    --   52.00  76.00 -90.85   56
 80  \w     92.00 117.00   0.50    0.20    --   52.00  77.00 154.67   50
 81  \w     28.00  71.00   0.50    0.20    --   52.00  77.00 154.67   86
 82  \w     75.00 102.00   0.50    0.20    --   56.00  69.00-147.47   54
 83  \w     34.00  60.00   0.50    0.20    --   56.00  69.00-147.47   52
 84  \w     32.00  58.00   0.50    0.20    --   56.00  75.00  64.84   52
 85  \w     41.00  73.00   0.50    0.20    --   60.00  66.00  70.93   64
 86  \w     36.00  63.00   0.50    0.20    --   60.00  75.00 -15.41   54
 87  \w     98.00 123.00   0.50    0.20    --   60.00  73.00 -57.02   50
 88  \w     37.00  64.00   0.50    0.20    --   60.00  73.00 -57.02   54
 89  \w     40.00  66.00   0.50    0.20    --   60.00  64.00  39.83   52
 90  \w    103.00 128.00   0.50    0.20    --   64.00  65.00 -88.62   50
 91  \w     45.00  98.00   0.50    0.20    --   64.00  65.00 -88.62  106
 92  \w     47.00  73.00   0.50    0.20    --   68.00  69.00 -14.54   52
 93  \w     86.00 113.00   0.50    0.20    --   68.00  69.00 -14.54   54
 94  \w     45.00  74.00   0.50    0.20    --   68.00  74.00 100.66   58
 95  \w     60.00  85.00   0.50    0.55    --   76.00  52.00 -44.15   50
 96  \w     63.00  88.00   0.50    0.55    --   76.00  45.00 144.22   50
 97  \w    111.00 143.00   0.50    0.55    --   80.00  66.00  50.83   64
 98  \w     59.00  91.00   0.50    0.55    --   80.00  66.00  50.83   64
 99  \w    115.00 145.00   0.50    0.55    --   84.00  74.00-161.19   60
100  \w     61.00  98.00   0.50    0.55    --   84.00  74.00-161.19   74
101  \w     65.00  91.00   0.50    0.55    --   88.00  74.00 165.71   52
102  \w    115.00 141.00   0.50    0.55    --  100.29  59.00  90.00   52
103  \w     75.00 101.00   0.50    0.55    --  100.29  77.00-150.00   52
104  \w     80.00 112.00   0.50    0.55    --  100.29  68.00  30.00   64
105  \w     83.00 108.00   0.50    0.55    --  100.29  59.00 -90.00   50
106  \w     75.00 140.00   0.50    0.55    --  100.29  77.00  30.00  130
107  \w     80.00 111.00   0.50    0.55    --  100.29  68.00 120.00   62
108  \w     76.00 122.00   0.50    0.55    --  100.29  77.00   0.00   92
109  \w     75.00 101.00   0.50    0.55    --  100.29  77.00-180.00   52
110  \w     79.00 155.00   0.50    0.55    --  100.29  68.00  60.00  152
111  \w     83.00 149.00   0.50    0.55    --  100.29  59.00 -30.00  132
112  \w     76.00 113.00   0.50    0.55    --  100.29  77.00 150.00   74
113  \w     75.00 101.00   0.50    0.55    --  100.29  77.00 120.00   52
114  \w    112.00 142.00   0.50    0.55    --  100.29  68.00   0.00   60
115  \w     79.00 107.00   0.50    0.55    --  100.29  68.00   0.00   56
116  \w    132.00 157.00   0.50    0.55    --  100.29  77.00 -90.00   50
117  \w    121.00 148.00   0.50    0.55    --  100.29  59.00 -90.00   54
118  \w     83.00 111.00   0.50    0.55    --  100.29  59.00  90.00   56
119  \w    107.00 157.00   0.50    0.55    --  100.29  77.00 -30.00  100
120  \w     37.00  83.00   0.50    0.55    --  100.29 -25.00-180.00   92
121  \w    132.00 157.00   0.50    0.55    --  100.29  77.00  60.00   50
122  \w    132.00 157.00   0.50    0.55    --  100.29  77.00-120.00   50
123  \w     76.00 103.00   0.50    0.55    --  100.29  77.00-120.00   54
124  \w     77.00 102.00   0.50    0.55    --  100.29  77.00 -90.00   50
125  \w     75.00 117.00   0.50    0.55    --  100.29  77.00  90.00   84
126  \w     88.00 148.00   0.50    0.55    --  100.29  59.00 -60.00  120
127  \w     76.00 101.00   0.50    0.55    --  100.29  77.00 -30.00   50
128  \w    132.00 157.00   0.50    0.55    --  100.29  77.00 -60.00   50
129  \w     75.00 102.00   0.50    0.55    --  100.29  77.00 -60.00   54
130  \w     79.00 105.00   0.50    0.55    --  100.29  68.00-120.00   52
131  \w     77.00 104.00   0.50    0.55    --  100.29  77.00  60.00   54
132  \w     85.00 110.00   0.50    0.55    --  100.29 146.00 -27.00   50
133  \w     46.00  72.00   0.50    0.20    --   64.00  58.00 -99.29   52
134  \w     59.00  84.00   0.50    0.55    --   76.00  58.00-178.79   50
135  \w     57.00  83.00   0.50    0.55    --   80.00  73.00 -25.20   52
136  \w     61.00  87.00   0.50    0.55    --   84.00  74.00  13.98   52
137  \w     65.00  92.00   0.50    0.55    --   88.00  73.00  87.91   54
;
_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      0.1737010000
_diffrn_orient_matrix_UB_12      -0.0377051000
_diffrn_orient_matrix_UB_13      -0.0676661000
_diffrn_orient_matrix_UB_21      0.0889163000
_diffrn_orient_matrix_UB_22      -0.0417385000
_diffrn_orient_matrix_UB_23      0.0893371000
_diffrn_orient_matrix_UB_31      -0.0265720000
_diffrn_orient_matrix_UB_32      -0.1512106000
_diffrn_orient_matrix_UB_33      -0.0091360000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19963
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.506
_diffrn_reflns_theta_min         3.226
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62941
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.043
_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     282
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.2487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3487
_reflns_number_total             4080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02916_si_002.cif
_cod_data_source_block           10190-pav-303
_cod_database_code               4033776
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.888
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C24(H24), C23(H23), C9(H9), C18(H18), C19(H19), C15(H15), C16(H16),
 C27(H27), C31(H31), C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_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 1.612
_oxdiff_exptl_absorpt_empirical_full_min 0.558