Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1<i>H</i>-pyrroles: Synthesis of Benzo/Furo/Thieno[<i>e</i>]-Fused 1<i>H</i>-Indol-7-oles and Their Transformations.
Bodunov, Vladimir A.; Galenko, Ekaterina E.; Sakharov, Pavel A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; The Journal of organic chemistry 84 (2019) 10388–10401; doi:10.1021/acs.joc.9b01573

data_4034061
_publ_section_title
;
 Selective Cu-Catalyzed Intramolecular Annulation of
 3-Aryl/Heteryl-2-(diazoacetyl)-1<i>H</i>-pyrroles: Synthesis of
 Benzo/Furo/Thieno[<i>e</i>]-Fused 1<i>H</i>-Indol-7-oles and Their
 Transformations.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10388
_journal_page_last               10401
_journal_paper_doi               10.1021/acs.joc.9b01573
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C15 H11 N O3'
_chemical_formula_sum            'C15 H11 N O3'
_chemical_formula_weight         253.25
_chemical_melting_point          217.0(10)
_chemical_name_common            quinone
_chemical_name_systematic        1-acetyl-2-methyl-3H-benzo[e]indole-4,5-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-02
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.304(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5184(2)
_cell_length_b                   10.7815(2)
_cell_length_c                   20.6909(5)
_cell_measurement_reflns_used    9391
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      72.6950
_cell_measurement_theta_min      4.3780
_cell_volume                     2283.46(8)
_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      115(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -68.00  -6.00   0.50    1.17    --  -38.95  85.00  56.00  124
  2  \w      5.00  59.00   0.50    1.17    --   38.95 -85.00 -62.00  108
  3  \w     78.00 157.00   0.50    4.67    --  104.92  85.00  56.00  158
  4  \w     36.00 135.00   0.50    4.67    --  104.92 -85.00 -62.00  198
  5  \w   -107.00 -82.00   0.50    1.17    --  -38.95 -21.00   0.00   50
  6  \w   -100.00 -30.00   0.50    1.17    --  -38.95 -32.00 -60.00  140
  7  \w    -80.00 -37.00   0.50    1.17    --  -38.95 -21.00   0.00   86
  8  \w    -52.00 -27.00   0.50    1.17    --  -38.95  43.00   0.00   50
  9  \w   -107.00 -26.00   0.50    1.17    --  -38.95 -32.00  90.00  162
 10  \w     26.00  56.00   0.50    1.17    --   38.95  32.00 120.00   60
 11  \w    -14.00  11.00   0.50    1.17    --   38.95 -43.00-150.00   50
 12  \w     13.00  54.00   0.50    1.17    --   38.95 -54.00 -30.00   82
 13  \w     45.00  97.00   0.50    1.17    --   38.95  65.00 150.00  104
 14  \w    -25.00   1.00   0.50    1.17    --   38.95 -54.00 -30.00   52
 15  \w     33.00  58.00   0.50    1.17    --   38.95  32.00-150.00   50
 16  \w     24.00  82.00   0.50    1.17    --   38.95  54.00  30.00  116
 17  \w     17.00  43.00   0.50    1.17    --   38.95 -43.00-150.00   52
 18  \w     52.00 127.00   0.50    4.67    --  104.92 -61.00 -90.00  150
 19  \w    100.00 144.00   0.50    4.67    --  104.92  37.00   0.00   88
 20  \w     85.00 120.00   0.50    4.67    --  104.92  77.00  30.00   70
 21  \w     85.00 111.00   0.50    4.67    --  104.92-133.00 -60.00   52
 22  \w    115.00 153.00   0.50    4.67    --  104.92  45.00 -60.00   76
 23  \w     86.00 152.00   0.50    4.67    --  104.92  22.00-150.00  132
 24  \w     87.00 156.00   0.50    4.67    --  104.92  69.00  90.00  138
 25  \w     46.00 114.00   0.50    4.67    --  104.92 -30.00 120.00  136
 26  \w     98.00 123.00   0.50    4.67    --  104.92 -45.00 -60.00   50
 27  \w     41.00  66.00   0.50    4.67    --  104.92 -45.00 -60.00   50
 28  \w     38.00  63.00   0.50    4.67    --  104.92-111.00  90.00   50
 29  \w    106.00 153.00   0.50    4.67    --  104.92 133.00 -90.00   94
 30  \w     87.00 156.00   0.50    4.67    --  104.92  45.00  30.00  138
 31  \w     85.00 147.00   0.50    4.67    --  104.92  53.00 -30.00  124
 32  \w     14.00  40.00   0.50    1.17    --   38.95  77.00-180.00   52
 33  \w    -42.00 -16.00   0.50    1.17    --  -38.95  21.00  30.00   52
 34  \w     -7.00  23.00   0.50    1.17    --  -38.95  43.00-180.00   60
 35  \w    -53.00 -17.00   0.50    1.17    --  -38.95  43.00-180.00   72
 36  \w     -3.00  23.00   0.50    1.17    --  -38.95  21.00  30.00   52
 37  \w      5.00  30.00   0.50    1.17    --  -38.95  32.00 -90.00   50
 38  \w    -51.00 -18.00   0.50    1.17    --  -38.95  32.00 -90.00   66
 39  \w    -33.00  -7.00   0.50    1.17    --   38.95 -21.00  30.00   52
 40  \w     14.00  53.00   0.50    1.17    --   38.95 -43.00 -60.00   78
 41  \w    -22.00   3.00   0.50    1.17    --   38.95 -43.00 -60.00   50
 42  \w     19.00  46.00   0.50    1.17    --   38.95 -21.00  30.00   54
 43  \w     27.00  52.00   0.50    1.17    --   38.95  32.00-120.00   50
 44  \w     73.00 105.00   0.50    1.17    --   38.95  77.00-180.00   64
 45  \w     12.00  38.00   0.50    1.17    --   38.95 -32.00-150.00   52
 46  \w     65.00  90.00   0.50    1.17    --   38.95  32.00-120.00   50
 47  \w     78.00 149.00   0.50    4.67    --  104.92  77.00 120.00  142
 48  \w     65.00 119.00   0.50    4.67    --  104.92 -61.00  90.00  108
 49  \w     69.00 122.00   0.50    4.67    --  104.92-133.00 120.00  106
 50  \w     90.00 151.00   0.50    4.67    --  104.92  93.00  30.00  122
 51  \w    131.00 157.00   0.50    4.67    --  104.92  30.00 150.00   52
 52  \w     34.00 106.00   0.50    4.67    --  104.92 -22.00 -60.00  144
 53  \w    121.00 147.00   0.50    4.67    --  104.92 111.00-150.00   52
 54  \w     80.00 120.00   0.50    4.67    --  104.92 111.00-150.00   80
 55  \w     55.00 123.00   0.50    4.67    --  104.92-133.00 -30.00  136
 56  \w     87.00 114.00   0.50    4.67    --  104.92-111.00 -30.00   54
 57  \w    132.00 157.00   0.50    4.67    --  104.92  69.00 150.00   50
 58  \w     38.00  64.00   0.50    4.67    --  104.92-111.00 -30.00   52
 59  \w     43.00  69.00   0.50    4.67    --  104.92 -45.00 -90.00   52
 60  \w     94.00 121.00   0.50    4.67    --  104.92 -45.00 -90.00   54
 61  \w     91.00 117.00   0.50    4.67    --  104.92  45.00-180.00   52
 62  \w     94.00 120.00   0.50    4.67    --  104.92  30.00  30.00   52
 63  \w     83.00 109.00   0.50    4.67    --  104.92  69.00-180.00   52
 64  \w     82.00 108.00   0.50    4.67    --  104.92  69.00 150.00   52
 65  \w     54.00  80.00   0.50    4.67    --  104.92-111.00  30.00   52
 66  \w     36.00  62.00   0.50    4.67    --  104.92 -30.00 -90.00   52
 67  \w     91.00 116.00   0.50    4.67    --  104.92  30.00 150.00   50
 68  \w    104.00 130.00   0.50    4.67    --  104.92  39.00 -81.00   52
 69  \w    -97.00 -72.00   0.50    1.17    --  -38.95 138.00-180.00   50
 70  \w    -52.00 -13.00   0.50    1.17    --  -38.95 138.00-180.00   78
 71  \w     47.00  89.00   0.50    1.17    --   38.95-138.00-120.00   84
 72  \w     35.00  61.00   0.50    1.17    --   38.95-104.00-120.00   52
 73  \w      7.00  33.00   0.50    1.17    --   38.95-104.00-120.00   52
 74  \w     32.00  59.00   0.50    1.17    --   38.95 -89.00  90.00   54
 75  \w     87.00 124.00   0.50    4.67    --  104.92-133.00 150.00   74
 76  \w    119.00 145.00   0.50    4.67    --  104.92  30.00 120.00   52
 77  \w     92.00 118.00   0.50    4.67    --  104.92  30.00 120.00   52
 78  \w     86.00 121.00   0.50    4.67    --  104.92 -61.00   0.00   70
 79  \w     48.00 126.00   0.50    4.67    --  104.92 -77.00 150.00  156
 80  \w     67.00 124.00   0.50    4.67    --  104.92 -53.00 150.00  114
 81  \w     81.00 113.00   0.50    4.67    --  104.92-111.00-180.00   64
 82  \w     46.00  92.00   0.50    4.67    --  104.92 -93.00 120.00   92
 83  \w    129.00 157.00   0.50    4.67    --  104.92  39.00 -81.00   56
 84  \w    -30.00  -5.00   0.50    1.17    --   16.00 117.00 -49.40   50
 85  \w    -32.00  -7.00   0.50    1.17    --   20.00 128.00  80.29   50
 86  \w    -17.00   8.00   0.50    1.17    --   24.00 110.00 171.17   50
 87  \w     -8.00  17.00   0.50    1.17    --   28.00 100.00 161.36   50
 88  \w     -6.00  19.00   0.50    1.17    --   28.00  97.00 -80.29   50
 89  \w     -1.00  24.00   0.50    1.17    --   32.00  94.00  93.02   50
 90  \w      5.00  30.00   0.50    1.17    --   36.00  89.00 -80.95   50
 91  \w      6.00  31.00   0.50    1.17    --   36.00  86.00  34.47   50
 92  \w      4.00  29.00   0.50    1.17    --   36.00  90.00-113.41   50
 93  \w      5.00  30.00   0.50    1.17    --   36.00  88.00 -14.83   50
 94  \w     34.00  59.00   0.50    1.17    --   38.95 -54.00  60.00   50
 95  \w    -18.00   8.00   0.50    1.17    --   38.95 -54.00  60.00   52
 96  \w     12.00  37.00   0.50    1.17    --   40.00  80.00 163.90   50
 97  \w     17.00  42.00   0.50    1.17    --   44.00  79.00-106.57   50
 98  \w     16.00  41.00   0.50    1.17    --   44.00  82.00  18.85   50
 99  \w     16.00  41.00   0.50    1.17    --   44.00  80.00 111.78   50
100  \w     16.00  41.00   0.50    1.17    --   44.00  82.00  75.69   50
101  \w     17.00  42.00   0.50    1.17    --   44.00  79.00-145.76   50
102  \w     17.00  42.00   0.50    1.17    --   44.00  79.00  -7.39   50
103  \w     16.00  41.00   0.50    1.17    --   44.00  81.00-168.50   50
104  \w     16.00  41.00   0.50    1.17    --   44.00  82.00  48.17   50
105  \w     16.00  41.00   0.50    1.17    --   44.00  81.00 -87.35   50
106  \w     31.00  57.00   0.50    1.17    --   56.00  74.00-175.50   52
107  \w     30.00  56.00   0.50    1.17    --   56.00  75.00 -56.23   52
108  \w     30.00  56.00   0.50    1.17    --   56.00  75.00  -9.02   52
109  \w     33.00  59.00   0.50    1.17    --   60.00  77.00 -85.98   52
110  \w     97.00 123.00   0.50    1.17    --   60.00  77.00 -85.98   52
111  \w     34.00  60.00   0.50    1.17    --   60.00  75.00 143.77   52
112  \w     38.00  79.00   0.50    1.17    --   60.00  69.00-145.87   82
113  \w     72.00  98.00   0.50    1.17    --   64.00  76.00  34.38   52
114  \w     39.00  65.00   0.50    1.17    --   64.00  76.00  34.38   52
115  \w     47.00  75.00   0.50    1.17    --   64.00  57.00 -77.38   56
116  \w     37.00  63.00   0.50    1.17    --   64.00  77.00 118.39   52
117  \w     40.00  66.00   0.50    1.17    --   64.00  73.00   2.25   52
118  \w     92.00 125.00   0.50    1.17    --   64.00  68.00-117.74   66
119  \w     40.00  82.00   0.50    1.17    --   64.00  68.00-117.74   84
120  \w     44.00  69.00   0.50    1.17    --   68.00  67.00  32.62   50
121  \w     43.00  69.00   0.50    1.17    --   68.00  72.00  71.34   52
122  \w     42.00  68.00   0.50    1.17    --   68.00  76.00  85.79   52
123  \w     48.00  91.00   0.50    4.67    --   72.00  68.00 -10.34   86
124  \w     47.00  79.00   0.50    4.67    --   72.00  76.00 -57.70   64
125  \w     48.00  79.00   0.50    4.67    --   72.00  75.00 166.02   62
126  \w     48.00  74.00   0.50    4.67    --   72.00  68.00 102.95   52
127  \w    121.00 146.00   0.50    4.67    --   80.00  70.00 -76.78   50
128  \w     55.00  81.00   0.50    4.67    --   80.00  70.00 -76.78   52
129  \w     55.00  81.00   0.50    4.67    --   80.00  72.00 107.21   52
130  \w     64.00  92.00   0.50    4.67    --   88.00  67.00  42.49   56
131  \w     63.00  89.00   0.50    4.67    --   88.00  70.00 125.61   52
132  \w     73.00  99.00   0.50    4.67    --   96.00  64.00 -23.98   52
133  \w     84.00 110.00   0.50    4.67    --  104.92  61.00-180.00   52
134  \w     78.00 104.00   0.50    4.67    --  104.92  77.00 -60.00   52
135  \w     90.00 116.00   0.50    4.67    --  104.92 -30.00 150.00   52
136  \w     42.00  67.00   0.50    4.67    --  104.92 -30.00 150.00   50
137  \w     87.00 113.00   0.50    4.67    --  104.92  77.00 150.00   52
138  \w    122.00 148.00   0.50    4.67    --  104.92  77.00 -30.00   52
139  \w     78.00 103.00   0.50    4.67    --  104.92  77.00  90.00   50
140  \w     80.00 106.00   0.50    4.67    --  104.92  77.00 -30.00   52
141  \w     83.00 109.00   0.50    4.67    --  104.92  61.00  60.00   52
142  \w     78.00 104.00   0.50    4.67    --  104.92  77.00  30.00   52
143  \w     78.00 113.00   0.50    4.67    --  104.92  77.00 -90.00   70
144  \w     83.00 133.00   0.50    4.67    --  104.92  61.00 120.00  100
145  \w    111.00 157.00   0.50    4.67    --  104.92 111.00 -60.00   92
146  \w     75.00 101.00   0.50    4.67    --  104.92 -22.00  30.00   52
147  \w     79.00 105.00   0.50    4.67    --  104.92  77.00   0.00   52
148  \w     80.00 120.00   0.50    4.67    --  104.92  77.00-150.00   80
149  \w    119.00 145.00   0.50    4.67    --  104.92  69.00-120.00   52
150  \w     39.00  72.00   0.50    4.67    --  104.92 -22.00  30.00   66
151  \w     81.00 107.00   0.50    4.67    --  104.92  69.00-120.00   52
152  \w     79.00 142.00   0.50    4.67    --  104.92  77.00-180.00  126
153  \w    117.00 143.00   0.50    4.67    --  104.92  69.00   0.00   52
154  \w    124.00 156.00   0.50    4.67    --  104.92  69.00-150.00   64
155  \w     81.00 106.00   0.50    4.67    --  104.92  69.00   0.00   50
156  \w     40.00  76.00   0.50    4.67    --  104.92 -45.00  60.00   72
157  \w     84.00 110.00   0.50    4.67    --  104.92  77.00-120.00   52
158  \w     81.00 106.00   0.50    4.67    --  104.92  69.00-150.00   50
;
_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      0.0085188000
_diffrn_orient_matrix_UB_12      -0.1266212000
_diffrn_orient_matrix_UB_13      0.0353397000
_diffrn_orient_matrix_UB_21      0.1502113000
_diffrn_orient_matrix_UB_22      0.0054217000
_diffrn_orient_matrix_UB_23      0.0138914000
_diffrn_orient_matrix_UB_31      0.0039830000
_diffrn_orient_matrix_UB_32      0.0660527000
_diffrn_orient_matrix_UB_33      0.0664089000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19517
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.473
_diffrn_reflns_theta_min         4.392
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75696
_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            red
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0552P)^2^+1.7540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2153
_reflns_number_total             2268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01573_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '216-218' was changed to
'217.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034061
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C15 N O2'
_shelx_estimated_absorpt_t_max   0.882
_shelx_estimated_absorpt_t_min   0.726
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C7(H7)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              43266
_shelx_hkl_checksum              9271
_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 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.617