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_4033777
_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         'C28 H24 N4'
_chemical_formula_sum            'C28 H24 N4'
_chemical_formula_weight         416.51
_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                90.152(3)
_cell_angle_beta                 93.927(4)
_cell_angle_gamma                97.454(4)
_cell_formula_units_Z            4
_cell_length_a                   11.3428(6)
_cell_length_b                   11.4979(5)
_cell_length_c                   17.2272(7)
_cell_measurement_reflns_used    13166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.9290
_cell_measurement_theta_min      2.5450
_cell_volume                     2222.38(18)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -91.00 -58.00   0.50    0.94    --  -41.35 -62.00  71.00   66
  2  \w    -22.00   9.00   0.50    0.94    --  -41.35  62.00-150.00   62
  3  \w    -60.00 -23.00   0.50    0.94    --  -41.35  62.00-150.00   74
  4  \w     23.00  75.00   0.50    0.94    --   41.35  62.00-150.00  104
  5  \w     87.00 147.00   0.50    3.76    --  101.00  62.00-150.00  120
  6  \w     39.00  86.00   0.50    3.76    --  101.00 -62.00  71.00   94
  7  \w    -97.00 -51.00   0.50    0.94    --  -41.35 138.00  60.00   92
  8  \w   -105.00 -63.00   0.50    0.94    --  -41.35 -65.00-120.00   84
  9  \w    -49.00  23.00   0.50    0.94    --  -41.35  32.00 -60.00  144
 10  \w    -70.00 -10.00   0.50    0.94    --  -41.35 104.00 -60.00  120
 11  \w    -79.00 -25.00   0.50    0.94    --  -41.35 -54.00 150.00  108
 12  \w    -95.00 -45.00   0.50    0.94    --  -41.35 138.00-180.00  100
 13  \w    -55.00  22.00   0.50    0.94    --  -41.35  54.00  30.00  154
 14  \w    -62.00 -21.00   0.50    0.94    --  -41.35 -65.00-120.00   82
 15  \w    -39.00  20.00   0.50    0.94    --  -41.35  43.00 150.00  118
 16  \w     74.00 102.00   0.50    0.94    --   41.35  65.00 -60.00   56
 17  \w    -19.00  27.00   0.50    0.94    --   41.35 -32.00-120.00   92
 18  \w     39.00  94.00   0.50    0.94    --   41.35  32.00   0.00  110
 19  \w     -6.00  62.00   0.50    0.94    --   41.35 -77.00   0.00  136
 20  \w     59.00  84.00   0.50    0.94    --   41.35  54.00 150.00   50
 21  \w    -14.00  17.00   0.50    0.94    --   41.35 -62.00  71.00   62
 22  \w     20.00  61.00   0.50    0.94    --   41.35 -65.00  30.00   82
 23  \w     29.00  55.00   0.50    0.94    --   41.35  54.00 150.00   52
 24  \w     38.00  91.00   0.50    0.94    --   41.35  32.00  60.00  106
 25  \w     37.00  77.00   0.50    3.76    --  101.00 -68.00 -30.00   80
 26  \w     35.00 109.00   0.50    3.76    --  101.00-111.00   0.00  148
 27  \w     41.00 110.00   0.50    3.76    --  101.00 -25.00 -60.00  138
 28  \w    116.00 144.00   0.50    3.76    --  101.00  42.00-150.00   56
 29  \w     89.00 114.00   0.50    3.76    --  101.00  42.00-150.00   50
 30  \w     93.00 141.00   0.50    3.76    --  101.00  25.00 -90.00   96
 31  \w     99.00 155.00   0.50    3.76    --  101.00  33.00  90.00  112
 32  \w     79.00 126.00   0.50    3.76    --  101.00 -87.00 -90.00   94
 33  \w     38.00  92.00   0.50    3.76    --  101.00 -42.00   0.00  108
 34  \w     42.00  93.00   0.50    3.76    --  101.00-111.00  60.00  102
 35  \w     39.00 104.00   0.50    3.76    --  101.00 -42.00-150.00  130
 36  \w     61.00 123.00   0.50    3.76    --  101.00-133.00 -90.00  124
 37  \w    127.00 154.00   0.50    3.76    --  101.00  93.00-150.00   54
 38  \w     48.00 131.00   0.50    3.76    --  101.00 -93.00  90.00  166
 39  \w     89.00 157.00   0.50    3.76    --  101.00  42.00 150.00  136
 40  \w     51.00 124.00   0.50    3.76    --  101.00-133.00 120.00  146
 41  \w    100.00 144.00   0.50    3.76    --  101.00  59.00 -60.00   88
 42  \w    104.00 155.00   0.50    3.76    --  101.00  50.00-180.00  102
 43  \w     86.00 148.00   0.50    3.76    --  101.00  93.00 -60.00  124
 44  \w     35.00  96.00   0.50    3.76    --  101.00-111.00 -90.00  122
 45  \w    123.00 154.00   0.50    3.76    --  101.00  50.00  30.00   62
 46  \w     85.00 112.00   0.50    3.76    --  101.00  50.00  30.00   54
 47  \w     44.00 114.00   0.50    3.76    --  101.00 -42.00  60.00  140
 48  \w     93.00 147.00   0.50    3.76    --  101.00  77.00 -90.00  108
 49  \w     83.00 157.00   0.50    3.76    --  101.00  93.00 -30.00  148
 50  \w     96.00 123.00   0.50    3.76    --  101.00 -68.00 -30.00   54
 51  \w     36.00 115.00   0.50    3.76    --  101.00-111.00 -60.00  158
 52  \w     81.00 120.00   0.50    3.76    --  101.00 -59.00-150.00   78
 53  \w     72.00 120.00   0.50    3.76    --  101.00 -59.00 120.00   96
 54  \w     94.00 127.00   0.50    3.76    --  101.00 -77.00  60.00   66
 55  \w     93.00 136.00   0.50    3.76    --  101.00  33.00 120.00   86
 56  \w     65.00  90.00   0.50    3.76    --  101.00 178.00   0.00   50
 57  \w     89.00 116.00   0.50    3.76    --  101.00  59.00  30.00   54
 58  \w    124.00 151.00   0.50    3.76    --  101.00  93.00 120.00   54
 59  \w    -26.00   1.00   0.50    0.94    --  -41.35  62.00-150.00   54
 60  \w    -47.00 -22.00   0.50    0.94    --    0.00 123.00  14.84   50
 61  \w    -37.00 -10.00   0.50    0.94    --   12.00 126.00 154.22   54
 62  \w    -42.00 -17.00   0.50    0.94    --   24.00 151.00 -16.49   50
 63  \w    -13.00  12.00   0.50    0.94    --   24.00 106.00-118.69   50
 64  \w     -4.00  21.00   0.50    0.94    --   28.00  97.00 118.91   50
 65  \w     -4.00  21.00   0.50    0.94    --   28.00  97.00-146.78   50
 66  \w      3.00  28.00   0.50    0.94    --   32.00  90.00  13.10   50
 67  \w      3.00  28.00   0.50    0.94    --   32.00  90.00-113.61   50
 68  \w      3.00  28.00   0.50    0.94    --   32.00  90.00 -65.12   50
 69  \w      9.00  34.00   0.50    0.94    --   36.00  85.00 -30.35   50
 70  \w      9.00  34.00   0.50    0.94    --   36.00  85.00 172.93   50
 71  \w      9.00  34.00   0.50    0.94    --   36.00  85.00  38.75   50
 72  \w     10.00  35.00   0.50    0.94    --   36.00  83.00-155.07   50
 73  \w      9.00  34.00   0.50    0.94    --   36.00  85.00  90.66   50
 74  \w     15.00  40.00   0.50    0.94    --   40.00  81.00 160.04   50
 75  \w     15.00  40.00   0.50    0.94    --   40.00  79.00 -26.54   50
 76  \w     19.00  44.00   0.50    0.94    --   44.00  80.00 -87.14   50
 77  \w     19.00  44.00   0.50    0.94    --   44.00  78.00 133.84   50
 78  \w     19.00  44.00   0.50    0.94    --   44.00  81.00 -61.55   50
 79  \w     19.00  44.00   0.50    0.94    --   44.00  78.00 114.62   50
 80  \w     19.00  44.00   0.50    0.94    --   44.00  79.00-121.40   50
 81  \w     18.00  43.00   0.50    0.94    --   44.00  82.00  11.67   50
 82  \w     26.00  53.00   0.50    0.94    --   48.00  77.00 177.74   54
 83  \w     27.00  54.00   0.50    0.94    --   52.00  77.00  26.62   54
 84  \w     28.00  54.00   0.50    0.94    --   52.00  77.00-144.80   52
 85  \w     32.00  59.00   0.50    0.94    --   56.00  76.00 -69.41   54
 86  \w     35.00  62.00   0.50    0.94    --   56.00  77.00  43.82   54
 87  \w     32.00  57.00   0.50    0.94    --   56.00  76.00-113.38   50
 88  \w     31.00  58.00   0.50    0.94    --   56.00  76.00  73.85   54
 89  \w     32.00  59.00   0.50    0.94    --   56.00  77.00 -47.69   54
 90  \w     31.00  57.00   0.50    0.94    --   56.00  76.00 134.27   52
 91  \w    104.00 129.00   0.50    0.94    --   64.00  77.00-106.62   50
 92  \w     40.00  65.00   0.50    0.94    --   64.00  77.00-106.62   50
 93  \w     40.00  65.00   0.50    0.94    --   64.00  76.00  26.43   50
 94  \w     39.00  89.00   0.50    0.94    --   64.00  77.00 133.60  100
 95  \w     42.00  68.00   0.50    0.94    --   64.00  71.00 -27.51   52
 96  \w     46.00  71.00   0.50    0.94    --   68.00  74.00 -20.70   50
 97  \w     44.00  74.00   0.50    0.94    --   68.00  77.00 -65.65   60
 98  \w     45.00  72.00   0.50    0.94    --   68.00  77.00 171.37   54
 99  \w     49.00  76.00   0.50    3.76    --   72.00  77.00  80.91   54
100  \w     48.00  77.00   0.50    3.76    --   72.00  77.00  27.20   58
101  \w     53.00  78.00   0.50    3.76    --   72.00  65.00-136.50   50
102  \w     47.00 104.00   0.50    3.76    --   72.00  77.00 138.38  114
103  \w     51.00  81.00   0.50    3.76    --   76.00  77.00  55.44   60
104  \w     89.00 116.00   0.50    3.76    --   76.00  77.00  91.02   54
105  \w     58.00  85.00   0.50    3.76    --   76.00  64.00 -83.51   54
106  \w     51.00  82.00   0.50    3.76    --   76.00  77.00  91.02   62
107  \w     54.00  83.00   0.50    3.76    --   76.00  74.00  -6.44   58
108  \w     58.00  98.00   0.50    3.76    --   80.00  70.00-118.04   80
109  \w     58.00 112.00   0.50    3.76    --   80.00  71.00-168.88  108
110  \w     62.00 120.00   0.50    3.76    --   84.00  71.00-147.69  116
111  \w     65.00  91.00   0.50    3.76    --   84.00  60.00-178.57   52
112  \w     63.00 112.00   0.50    3.76    --   88.00  77.00   4.71   98
113  \w    102.00 148.00   0.50    3.76    --   88.00  71.00 -52.27   92
114  \w     66.00  92.00   0.50    3.76    --   88.00  71.00 -52.27   52
115  \w     68.00  93.00   0.50    3.76    --   92.00  77.00-103.31   50
116  \w    119.00 148.00   0.50    3.76    --  101.00  76.00 170.85   58
117  \w     76.00 103.00   0.50    3.76    --  101.00  76.00 170.85   54
118  \w     81.00 107.00   0.50    3.76    --  101.00  68.00-120.00   52
119  \w     82.00 109.00   0.50    3.76    --  101.00 -42.00 -90.00   54
120  \w     77.00 102.00   0.50    3.76    --  101.00  77.00 -30.00   50
121  \w     77.00 104.00   0.50    3.76    --  101.00  77.00-180.00   54
122  \w     38.00  65.00   0.50    3.76    --  101.00 -42.00 -90.00   54
123  \w    121.00 148.00   0.50    3.76    --  101.00  77.00   0.00   54
124  \w    130.00 157.00   0.50    3.76    --  101.00  77.00  60.00   54
125  \w     76.00 103.00   0.50    3.76    --  101.00  77.00  60.00   54
126  \w     77.00 102.00   0.50    3.76    --  101.00  77.00   0.00   50
127  \w    117.00 144.00   0.50    3.76    --  101.00  77.00-150.00   54
128  \w     83.00 136.00   0.50    3.76    --  101.00  59.00 120.00  106
129  \w    132.00 157.00   0.50    3.76    --  101.00  77.00 150.00   50
130  \w     77.00 102.00   0.50    3.76    --  101.00  77.00-150.00   50
131  \w    112.00 151.00   0.50    3.76    --  101.00  59.00 -30.00   78
132  \w     84.00 111.00   0.50    3.76    --  101.00  59.00 -30.00   54
133  \w    131.00 156.00   0.50    3.76    --  101.00  77.00-120.00   50
134  \w     77.00 102.00   0.50    3.76    --  101.00  77.00-120.00   50
135  \w     83.00 145.00   0.50    3.76    --  101.00  59.00 -90.00  124
136  \w    129.00 156.00   0.50    3.76    --  101.00  59.00  60.00   54
137  \w     86.00 113.00   0.50    3.76    --  101.00  59.00  60.00   54
138  \w     74.00 109.00   0.50    3.76    --  101.00 -33.00 120.00   70
139  \w     45.00  70.00   0.50    3.76    --  101.00 -33.00 120.00   50
140  \w     76.00 110.00   0.50    3.76    --  101.00  77.00 120.00   68
141  \w     44.00 109.00   0.50    3.76    --  101.00 -25.00  30.00  130
142  \w    121.00 155.00   0.50    3.76    --  101.00  59.00   0.00   68
143  \w    116.00 151.00   0.50    3.76    --  101.00  77.00 -60.00   70
144  \w    130.00 157.00   0.50    3.76    --  101.00  68.00  81.17   54
145  \w     85.00 118.00   0.50    3.76    --  101.00  59.00   0.00   66
146  \w     76.00 103.00   0.50    3.76    --  101.00  77.00 -60.00   54
147  \w    116.00 154.00   0.50    3.76    --  101.00  68.00 120.00   76
148  \w     80.00 106.00   0.50    3.76    --  101.00  68.00 120.00   52
149  \w    124.00 156.00   0.50    3.76    --  101.00  77.00  30.00   64
150  \w     80.00 106.00   0.50    3.76    --  101.00  68.00  81.17   52
151  \w    128.00 153.00   0.50    3.76    --  101.00  77.00  90.00   50
152  \w     77.00 105.00   0.50    3.76    --  101.00  77.00  90.00   56
153  \w     76.00 121.00   0.50    3.76    --  101.00  77.00 150.00   90
154  \w     76.00 112.00   0.50    3.76    --  101.00  77.00  30.00   72
155  \w     77.00 102.00   0.50    3.76    --  101.00  77.00 -90.00   50
156  \w    113.00 140.00   0.50    3.76    --  101.00  68.00-120.00   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      0.0645131000
_diffrn_orient_matrix_UB_12      -0.0801413000
_diffrn_orient_matrix_UB_13      -0.0496719000
_diffrn_orient_matrix_UB_21      -0.0597597000
_diffrn_orient_matrix_UB_22      -0.1082946000
_diffrn_orient_matrix_UB_23      0.0415075000
_diffrn_orient_matrix_UB_31      -0.1054528000
_diffrn_orient_matrix_UB_32      -0.0105728000
_diffrn_orient_matrix_UB_33      -0.0620136000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48068
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_min         2.571
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79090
_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    1.245
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.072
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         8376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0721
_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^)+(0.1301P)^2^+1.1521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2015
_refine_ls_wR_factor_ref         0.2213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6375
_reflns_number_total             8376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02916_si_003.cif
_cod_data_source_block           5699-10169_gai-862
_cod_database_code               4033777
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C28 H24 N4'
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_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:
 C26(H26A,H26B), C26A(H26C,H26D)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C25(H25), C10(H10), C10A(H10A), C25A(H25A), C32A(H32A), C9A(H9A),
 C14(H14), C24A(H24A), C31A(H31A), C24(H24), C14A(H14A), C13A(H13A), C23(H23),
 C13(H13), C22(H22), C30A(H30A), C32(H32), C28(H28), C28A(H28A), C29(H29),
 C31(H31), C22A(H22A), C30(H30), C29A(H29A), C23A(H23A)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C12A(H12D,H12E,H12F), C21(H21A,H21B,
 H21C), C20A(H20D,H20E,H20F), C21A(H21D,H21E,H21F)
;
_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 4.497
_oxdiff_exptl_absorpt_empirical_full_min 0.409