Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes fused to Indole, Triazole and Isocoumarin.
Danilkina, Natalia A.; D'yachenko, Alexander; Govdi, Anastasia I.; Khlebnikov, Alexander F.; Kornyakov, Ilya; Bräse, Stefan; Balova, Irina A.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00930

data_4038528
_publ_section_title
;
 Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes
 fused to Indole, Triazole and Isocoumarin.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00930
_journal_year                    2020
_chemical_formula_moiety         'C22 H10 Co2 O9'
_chemical_formula_sum            'C22 H10 Co2 O9'
_chemical_formula_weight         536.16
_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             2018-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                105.8038(9)
_cell_angle_beta                 105.6810(9)
_cell_angle_gamma                105.5086(10)
_cell_formula_units_Z            4
_cell_length_a                   13.17979(14)
_cell_length_b                   13.56640(15)
_cell_length_c                   13.59048(12)
_cell_measurement_reflns_used    21658
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6040
_cell_measurement_theta_min      3.6150
_cell_volume                     2093.08(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.990
_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    -66.00 -23.00   0.50    3.00    --  -38.82  78.00-104.00   86
  2  \w     21.00  47.00   0.50    3.00    --   38.82 -78.00 130.00   52
  3  \w     38.00 108.00   0.50    9.00    --  102.95 -78.00 130.00  140
  4  \w    115.00 152.00   0.50    9.00    --  102.95  78.00-104.00   74
  5  \w    -34.00  30.00   0.50    3.00    --  -38.82  21.00-180.00  128
  6  \w    -49.00 -10.00   0.50    3.00    --  -38.82  32.00  60.00   78
  7  \w     -6.00  27.00   0.50    3.00    --  -38.82  32.00  60.00   66
  8  \w    -69.00 -22.00   0.50    3.00    --  -38.82 -54.00  30.00   94
  9  \w     -8.00  18.00   0.50    3.00    --  -38.82  54.00-150.00   52
 10  \w   -102.00 -75.00   0.50    3.00    --  -38.82 -54.00  30.00   54
 11  \w    -59.00 -10.00   0.50    3.00    --  -38.82  54.00-150.00   98
 12  \w    -22.00   3.00   0.50    3.00    --   38.82 -43.00 150.00   50
 13  \w     59.00 110.00   0.50    3.00    --   38.82  11.00 -90.00  102
 14  \w     58.00 104.00   0.50    3.00    --   38.82  32.00 -60.00   92
 15  \w     10.00  48.00   0.50    3.00    --   38.82 -32.00-180.00   76
 16  \w     22.00  48.00   0.50    3.00    --   38.82  11.00 -90.00   52
 17  \w     82.00 107.00   0.50    3.00    --   38.82  32.00-180.00   50
 18  \w     16.00  48.00   0.50    3.00    --   38.82 -43.00 150.00   64
 19  \w     88.00 157.00   0.50    9.00    --  102.95  50.00 -60.00  138
 20  \w     93.00 153.00   0.50    9.00    --  102.95  25.00   0.00  120
 21  \w    124.00 156.00   0.50    9.00    --  102.95 111.00-180.00   64
 22  \w     81.00 143.00   0.50    9.00    --  102.95  93.00-150.00  124
 23  \w     88.00 113.00   0.50    9.00    --  102.95  25.00 -60.00   50
 24  \w     66.00 119.00   0.50    9.00    --  102.95 -25.00  90.00  106
 25  \w     55.00 120.00   0.50    9.00    --  102.95 -42.00 150.00  130
 26  \w    132.00 157.00   0.50    9.00    --  102.95  25.00 -60.00   50
 27  \w     43.00  72.00   0.50    9.00    --  102.95-111.00  60.00   58
 28  \w     39.00 113.00   0.50    9.00    --  102.95-111.00 150.00  148
 29  \w     49.00  76.00   0.50    9.00    --  102.95 -77.00-150.00   54
 30  \w    103.00 130.00   0.50    9.00    --  102.95 -77.00-150.00   54
 31  \w     43.00  96.00   0.50    9.00    --  102.95 -59.00 -60.00  106
 32  \w    125.00 153.00   0.50    9.00    --  102.95  17.00-150.00   56
 33  \w     82.00 117.00   0.50    9.00    --  102.95  17.00-150.00   70
 34  \w     94.00 119.00   0.50    9.00    --  102.95  78.00-104.00   50
 35  \w    -96.00 -70.00   0.50    3.00    --  -38.82 -54.00 150.00   52
 36  \w    -51.00 -23.00   0.50    3.00    --  -38.82 -43.00-180.00   56
 37  \w   -102.00 -59.00   0.50    3.00    --  -38.82 -43.00-180.00   86
 38  \w    -56.00 -18.00   0.50    3.00    --  -38.82 -54.00 150.00   76
 39  \w    -31.00  15.00   0.50    3.00    --  -38.82  32.00 120.00   92
 40  \w     20.00  51.00   0.50    3.00    --   38.82 -54.00  30.00   62
 41  \w     48.00  74.00   0.50    3.00    --   38.82  32.00-150.00   52
 42  \w     67.00  93.00   0.50    3.00    --   38.82  43.00   0.00   52
 43  \w     17.00  45.00   0.50    3.00    --   38.82  65.00   0.00   56
 44  \w     82.00 108.00   0.50    3.00    --   38.82  32.00  60.00   52
 45  \w     55.00  81.00   0.50    3.00    --   38.82  32.00  60.00   52
 46  \w    -26.00   0.00   0.50    3.00    --   38.82 -65.00-150.00   52
 47  \w    -22.00  10.00   0.50    3.00    --   38.82 -54.00  30.00   64
 48  \w     21.00  47.00   0.50    3.00    --   38.82 -65.00-150.00   52
 49  \w     57.00 101.00   0.50    3.00    --   38.82  65.00   0.00   88
 50  \w     41.00  66.00   0.50    9.00    --  102.95-133.00 -60.00   50
 51  \w    104.00 130.00   0.50    9.00    --  102.95  77.00 150.00   52
 52  \w    121.00 148.00   0.50    9.00    --  102.95  59.00   0.00   54
 53  \w     46.00 100.00   0.50    9.00    --  102.95 -25.00  60.00  108
 54  \w     81.00 107.00   0.50    9.00    --  102.95  59.00   0.00   52
 55  \w     80.00 140.00   0.50    9.00    --  102.95 133.00-150.00  120
 56  \w     76.00 102.00   0.50    9.00    --  102.95  77.00   0.00   52
 57  \w     55.00  84.00   0.50    9.00    --  102.95 -68.00 150.00   58
 58  \w    129.00 154.00   0.50    9.00    --  102.95  68.00  30.00   50
 59  \w     88.00 114.00   0.50    9.00    --  102.95-133.00 120.00   52
 60  \w     36.00 110.00   0.50    9.00    --  102.95-111.00 -60.00  148
 61  \w     79.00 105.00   0.50    9.00    --  102.95  68.00  30.00   52
 62  \w    132.00 157.00   0.50    9.00    --  102.95  17.00-180.00   50
 63  \w     76.00 102.00   0.50    9.00    --  102.95  77.00 -30.00   52
 64  \w    122.00 148.00   0.50    9.00    --  102.95  77.00 -30.00   52
 65  \w     43.00  84.00   0.50    9.00    --  102.95-133.00 120.00   82
 66  \w     80.00 113.00   0.50    9.00    --  102.95  17.00-180.00   66
 67  \w     74.00 122.00   0.50    9.00    --  102.95-133.00 -60.00   96
 68  \w    122.00 148.00   0.50    9.00    --  102.95  93.00 -60.00   52
 69  \w     87.00 113.00   0.50    9.00    --  102.95  50.00 -30.00   52
 70  \w    132.00 157.00   0.50    9.00    --  102.95  50.00  90.00   50
 71  \w    123.00 149.00   0.50    9.00    --  102.95  93.00   0.00   52
 72  \w     80.00 112.00   0.50    9.00    --  102.95  68.00   0.00   64
 73  \w     86.00 141.00   0.50    9.00    --  102.95  50.00  60.00  110
 74  \w     82.00 124.00   0.50    9.00    --  102.95-133.00  90.00   84
 75  \w     37.00 105.00   0.50    9.00    --  102.95 -42.00  90.00  136
 76  \w     85.00 157.00   0.50    9.00    --  102.95  50.00  30.00  144
 77  \w    -71.00 -45.00   0.50    5.00    --  -38.82  96.00  87.00   52
 78  \w    -46.00 -18.00   0.50    5.00    --    0.00 118.00 -49.50   56
 79  \w    -48.00 -22.00   0.50    5.00    --   24.00 159.00 -76.93   52
 80  \w    -44.00 -19.00   0.50    5.00    --   24.00 152.00 102.19   50
 81  \w     -9.00  16.00   0.50    5.00    --   28.00 102.00 176.68   50
 82  \w     -1.00  24.00   0.50    5.00    --   32.00  94.00 -47.59   50
 83  \w     -1.00  24.00   0.50    5.00    --   32.00  94.00-144.31   50
 84  \w     -1.00  24.00   0.50    5.00    --   32.00  94.00  97.98   50
 85  \w      0.00  25.00   0.50    5.00    --   32.00  91.00  29.97   50
 86  \w      6.00  31.00   0.50    5.00    --   36.00  86.00-179.99   50
 87  \w      6.00  31.00   0.50    5.00    --   36.00  86.00-140.89   50
 88  \w    -53.00 -14.00   0.50    5.00    --  -38.82 138.00-120.00   78
 89  \w    -43.00 -16.00   0.50    5.00    --  -38.82  96.00  87.00   54
 90  \w    -96.00 -60.00   0.50    5.00    --  -38.82 138.00-120.00   72
 91  \w      9.00  35.00   0.50    5.00    --   38.82 -89.00 -30.00   52
 92  \w      9.00  34.00   0.50    5.00    --   38.82  85.00  -2.39   50
 93  \w     41.00  91.00   0.50    5.00    --   38.82-138.00 150.00  100
 94  \w     -1.00  63.00   0.50    5.00    --   38.82 -89.00 -60.00  128
 95  \w      9.00  34.00   0.50    5.00    --   38.82  85.00  48.29   50
 96  \w     44.00  70.00   0.50    5.00    --   38.82 -89.00 -30.00   52
 97  \w     11.00  36.00   0.50    5.00    --   40.00  84.00 -88.46   50
 98  \w     16.00  41.00   0.50    5.00    --   44.00  82.00 131.62   50
 99  \w     17.00  42.00   0.50    5.00    --   44.00  79.00-174.91   50
100  \w     16.00  41.00   0.50    5.00    --   44.00  80.00-129.87   50
101  \w     16.00  41.00   0.50    5.00    --   44.00  81.00 -34.72   50
102  \w     16.00  41.00   0.50    5.00    --   44.00  80.00  99.36   50
103  \w     16.00  44.00   0.50    5.00    --   44.00  80.00  34.26   56
104  \w     16.00  41.00   0.50    5.00    --   44.00  81.00 -58.39   50
105  \w     16.00  41.00   0.50    5.00    --   44.00  82.00  -5.65   50
106  \w     25.00  51.00   0.50    5.00    --   52.00  77.00 138.34   52
107  \w     26.00  52.00   0.50    5.00    --   52.00  77.00-122.29   52
108  \w     27.00  53.00   0.50    5.00    --   52.00  75.00 -51.77   52
109  \w     31.00  57.00   0.50    5.00    --   56.00  73.00 175.62   52
110  \w     97.00 122.00   0.50    5.00    --   56.00  75.00  96.05   50
111  \w     35.00  74.00   0.50    5.00    --   56.00  73.00-146.28   78
112  \w     30.00  69.00   0.50    5.00    --   56.00  74.00  -1.40   78
113  \w     34.00 102.00   0.50    5.00    --   56.00  75.00 134.17  136
114  \w     30.00  61.00   0.50    5.00    --   56.00  74.00  75.66   62
115  \w     34.00  74.00   0.50    5.00    --   56.00  75.00  96.05   80
116  \w     35.00  61.00   0.50    5.00    --   60.00  70.00  32.95   52
117  \w     35.00 124.00   0.50    5.00    --   60.00  74.00  80.89  178
118  \w     39.00  76.00   0.50    5.00    --   64.00  76.00-114.80   74
119  \w     97.00 128.00   0.50    5.00    --   64.00  76.00  34.55   62
120  \w     38.00  76.00   0.50    5.00    --   64.00  76.00  34.55   76
121  \w     37.00  70.00   0.50    5.00    --   64.00  77.00 -89.65   66
122  \w     37.00  73.00   0.50    5.00    --   64.00  77.00 -45.99   72
123  \w     41.00  66.00   0.50    5.00    --   68.00  77.00-176.78   50
124  \w    118.00 143.00   0.50   20.00    --   76.00  77.00-165.01   50
125  \w     49.00  83.00   0.50   20.00    --   76.00  77.00-165.01   68
126  \w     54.00  81.00   0.50   20.00    --   76.00  59.00 -15.62   54
127  \w     60.00  86.00   0.50   20.00    --   80.00  53.00 -57.49   52
128  \w    119.00 145.00   0.50   20.00    --   80.00  71.00 160.17   52
129  \w     56.00  82.00   0.50   20.00    --   80.00  71.00 160.17   52
130  \w    113.00 152.00   0.50   20.00    --  102.95  59.00-180.00   78
131  \w    131.00 156.00   0.50   20.00    --  102.95  77.00  60.00   50
132  \w     81.00 106.00   0.50   20.00    --  102.95  59.00-180.00   50
133  \w     76.00 103.00   0.50   20.00    --  102.95  77.00  60.00   54
134  \w    120.00 145.00   0.50   20.00    --  102.95  68.00  60.00   50
135  \w     79.00 104.00   0.50   20.00    --  102.95  68.00  60.00   50
136  \w     76.00 102.00   0.50   20.00    --  102.95  77.00 150.00   52
137  \w     84.00 129.00   0.50   20.00    --  102.95  59.00  90.00   90
138  \w    132.00 157.00   0.50   20.00    --  102.95  77.00-180.00   50
139  \w    127.00 153.00   0.50   20.00    --  102.95  77.00  30.00   52
140  \w     76.00 102.00   0.50   20.00    --  102.95  77.00  30.00   52
141  \w     76.00 101.00   0.50   20.00    --  102.95  77.00-150.00   50
142  \w     77.00 121.00   0.50   20.00    --  102.95  77.00 -90.00   88
143  \w    129.00 155.00   0.50   20.00    --  102.95  93.00 150.00   52
144  \w     44.00 105.00   0.50   20.00    --  102.95-133.00 150.00  122
145  \w     76.00 114.00   0.50   20.00    --  102.95  77.00-180.00   76
146  \w     37.00  69.00   0.50   20.00    --  102.95 -68.00 -90.00   64
147  \w     81.00 107.00   0.50   20.00    --  102.95  59.00 -60.00   52
148  \w     76.00 102.00   0.50   20.00    --  102.95  77.00 -60.00   52
149  \w    108.00 135.00   0.50   20.00    --  102.95 -93.00 -30.00   54
150  \w    126.00 156.00   0.50   20.00    --  102.95  59.00 120.00   60
151  \w    131.00 157.00   0.50   20.00    --  102.95  68.00 120.00   52
152  \w     80.00 105.00   0.50   20.00    --  102.95  68.00 120.00   50
153  \w     46.00 102.00   0.50   20.00    --  102.95 -93.00 -30.00  112
154  \w     83.00 109.00   0.50   20.00    --  102.95  59.00-120.00   52
155  \w     76.00 102.00   0.50   20.00    --  102.95  77.00 120.00   52
156  \w     79.00 146.00   0.50   20.00    --  102.95  68.00-150.00  134
157  \w     81.00  95.50   0.50   20.00    --  102.95  59.00 120.00   29
;
_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      0.0709469000
_diffrn_orient_matrix_UB_12      -0.0170848000
_diffrn_orient_matrix_UB_13      0.0999283000
_diffrn_orient_matrix_UB_21      -0.0714043000
_diffrn_orient_matrix_UB_22      0.0374468000
_diffrn_orient_matrix_UB_23      0.0645796000
_diffrn_orient_matrix_UB_31      -0.0831723000
_diffrn_orient_matrix_UB_32      -0.1200710000
_diffrn_orient_matrix_UB_33      -0.0438741000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38139
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.952
_diffrn_reflns_theta_min         3.638
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_description       tables
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         8143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0705P)^2^+0.3244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7278
_reflns_number_total             8143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00930_si_003.cif
_cod_data_source_block           das148
_cod_original_cell_volume        2093.08(4)
_cod_database_code               4038528
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C88  H40  Co8  O36  '
_reflns_odcompleteness_completeness 99.92
_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
2.a Secondary CH2 refined with riding coordinates:
 C17A(H17C,H17D), C15A(H15C,H15D), C14A(H14C,H14D), C17(H17A,H17B), C15(H15A,
 H15B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7(H7), C4A(H4A), C4(H4), C6A(H6A), C5(H5), C5A(H5A), C6(H6)
;
_shelx_res_checksum              39240
_shelx_hkl_checksum              22697
_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 2.895
_oxdiff_exptl_absorpt_empirical_full_min 0.558