Isoxazole Strategy for the Synthesis of α-Aminopyrrole Derivatives.
Galenko, Ekaterina E.; Linnik, Stanislav A.; Khoroshilova, Olesya V.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; The Journal of organic chemistry 84 (2019) 11275–11285; doi:10.1021/acs.joc.9b01634

data_4033880
_publ_section_title
;
 Isoxazole Strategy for the Synthesis of \a-Aminopyrrole Derivatives.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11275
_journal_page_last               11285
_journal_paper_doi               10.1021/acs.joc.9b01634
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C20 H17 N3 O4'
_chemical_formula_sum            'C20 H17 N3 O4'
_chemical_formula_weight         363.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.1900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8922(2)
_cell_length_b                   4.84960(10)
_cell_length_c                   19.7030(3)
_cell_measurement_reflns_used    16111
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.7500
_cell_measurement_theta_min      3.0850
_cell_volume                     1687.69(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 1.000
_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   -110.00 -31.00   0.50    0.50    --  -38.82 -25.00-129.00  158
  2  \w    -37.00   7.00   0.50    0.50    --  -38.82  25.00  34.00   88
  3  \w      0.00  45.00   0.50    0.50    --   38.82 -25.00-129.00   90
  4  \w     41.00  78.00   0.50    0.50    --   38.82  25.00  34.00   74
  5  \w     37.00 123.00   0.50    2.00    --  107.00 -25.00-129.00  172
  6  \w    106.00 132.00   0.50    2.00    --  107.00  25.00  34.00   52
  7  \w    -15.00  11.00   0.50    0.50    --   38.82 -54.00 120.00   52
  8  \w     75.00 105.00   0.50    0.50    --   38.82  77.00-180.00   60
  9  \w     -1.00  61.00   0.50    0.50    --   38.82 -77.00  90.00  124
 10  \w    -26.00  55.00   0.50    0.50    --   38.82 -43.00-180.00  162
 11  \w     20.00  45.00   0.50    0.50    --   38.82  77.00-180.00   50
 12  \w     16.00  58.00   0.50    0.50    --   38.82 -54.00 120.00   84
 13  \w     19.00  59.00   0.50    0.50    --   38.82 -54.00-120.00   80
 14  \w    -17.00  35.00   0.50    0.50    --   38.82 -21.00 -30.00  104
 15  \w     77.00 105.00   0.50    0.50    --   38.82  43.00 150.00   56
 16  \w     29.00  57.00   0.50    0.50    --   38.82  43.00 150.00   56
 17  \w     52.00  77.00   0.50    0.50    --   38.82  32.00-120.00   50
 18  \w     80.00 106.00   0.50    2.00    --  107.00-111.00 120.00   52
 19  \w     54.00  89.00   0.50    2.00    --  107.00 -30.00 -60.00   70
 20  \w    108.00 153.00   0.50    2.00    --  107.00  22.00  60.00   90
 21  \w     51.00 106.00   0.50    2.00    --  107.00-111.00 -60.00  110
 22  \w    114.00 156.00   0.50    2.00    --  107.00  30.00 -90.00   84
 23  \w     46.00  72.00   0.50    2.00    --  107.00 -53.00-150.00   52
 24  \w     76.00 119.00   0.50    2.00    --  107.00 -30.00 150.00   86
 25  \w     42.00 105.00   0.50    2.00    --  107.00 -61.00 -90.00  126
 26  \w     95.00 120.00   0.50    2.00    --  107.00 -77.00-150.00   50
 27  \w     48.00  88.00   0.50    2.00    --  107.00 -77.00-150.00   80
 28  \w    102.00 127.00   0.50    2.00    --  107.00 -53.00-150.00   50
 29  \w     38.00  63.00   0.50    2.00    --  107.00 -30.00 150.00   50
 30  \w     40.00  67.00   0.50    2.00    --  107.00-111.00-180.00   54
 31  \w     41.00 132.00   0.50    2.00    --  107.00 -69.00   0.00  182
 32  \w     96.00 121.00   0.50    2.00    --  107.00 -30.00 -60.00   50
 33  \w     42.00 107.00   0.50    2.00    --  107.00 -93.00   0.00  130
 34  \w     46.00  76.00   0.50    2.00    --  107.00 -37.00   0.00   60
 35  \w     59.00 102.00   0.50    0.50    --   38.82  11.00 150.00   86
 36  \w    -12.00  14.00   0.50    0.50    --  -38.82  32.00-180.00   52
 37  \w    -61.00 -12.00   0.50    0.50    --  -38.82 -77.00-180.00   98
 38  \w     14.00  77.00   0.50    0.50    --   38.82  77.00-180.00  126
 39  \w     21.00  46.00   0.50    0.50    --   38.82  54.00-120.00   50
 40  \w     23.00  64.00   0.50    0.50    --   38.82  65.00 150.00   82
 41  \w     30.00  57.00   0.50    0.50    --   38.82  43.00 120.00   54
 42  \w     13.00  69.00   0.50    0.50    --   38.82  77.00 150.00  112
 43  \w     13.00  54.00   0.50    0.50    --   38.82  77.00 120.00   82
 44  \w     87.00 114.00   0.50    2.00    --  107.00  53.00-150.00   54
 45  \w     88.00 114.00   0.50    2.00    --  107.00  53.00 120.00   52
 46  \w    130.00 156.00   0.50    2.00    --  107.00  61.00-180.00   52
 47  \w     80.00 150.00   0.50    2.00    --  107.00  77.00  60.00  140
 48  \w     80.00 106.00   0.50    2.00    --  107.00  77.00 120.00   52
 49  \w    132.00 157.00   0.50    2.00    --  107.00  77.00 120.00   50
 50  \w     80.00 106.00   0.50    2.00    --  107.00  77.00 150.00   52
 51  \w    125.00 151.00   0.50    2.00    --  107.00  77.00  90.00   52
 52  \w     85.00 156.00   0.50    2.00    --  107.00  61.00 120.00  142
 53  \w     92.00 121.00   0.50    2.00    --  107.00  45.00 120.00   58
 54  \w     85.00 148.00   0.50    2.00    --  107.00  61.00  90.00  126
 55  \w     83.00 146.00   0.50    2.00    --  107.00  69.00 150.00  126
 56  \w     86.00 112.00   0.50    2.00    --  107.00  61.00-150.00   52
 57  \w     80.00 105.00   0.50    2.00    --  107.00  81.00 124.23   50
 58  \w     91.00 119.00   0.50    2.00    --  107.00  45.00-150.00   56
 59  \w     80.00 106.00   0.50    2.00    --  107.00  77.00  90.00   52
 60  \w    132.00 157.00   0.50    2.00    --  107.00  77.00-180.00   50
 61  \w     87.00 112.00   0.50    2.00    --  107.00  53.00  90.00   50
 62  \w     83.00 108.00   0.50    2.00    --  107.00  69.00-180.00   50
 63  \w     83.00 108.00   0.50    2.00    --  107.00  69.00  90.00   50
 64  \w     83.00 109.00   0.50    2.00    --  107.00  69.00 120.00   52
 65  \w     85.00 111.00   0.50    2.00    --  107.00  61.00 150.00   52
 66  \w     87.00 120.00   0.50    2.00    --  107.00  53.00-180.00   66
 67  \w     80.00 106.00   0.50    2.00    --  107.00  77.00-180.00   52
 68  \w     84.00 116.00   0.50    2.00    --  107.00  69.00  60.00   64
 69  \w     80.00 109.00   0.50    2.00    --  107.00  78.00  37.53   58
 70  \w    132.00 157.00   0.50    2.00    --  107.00  53.00-150.00   50
 71  \w     85.00 135.00   0.50    2.00    --  107.00  61.00  60.00  100
 72  \w     85.00 125.00   0.50    2.00    --  107.00  61.00-180.00   80
 73  \w     90.00 115.00   0.50    2.00    --  107.00  45.00 150.00   50
 74  \w     91.00 137.00   0.50    2.00    --  107.00  53.00 150.00   92
 75  \w     31.00  74.00   0.50    0.50    --   38.82-106.00  40.00   86
 76  \w    -90.00 -59.00   0.50    0.50    --  -38.82 138.00 -60.00   62
 77  \w    -94.00 -55.00   0.50    0.50    --  -38.82 138.00-150.00   78
 78  \w     54.00  95.00   0.50    0.50    --   38.82-138.00  30.00   82
 79  \w     15.00  61.00   0.50    0.50    --   38.82-138.00 120.00   92
 80  \w     84.00 110.00   0.50    2.00    --  107.00-111.00 -30.00   52
 81  \w     61.00 102.00   0.50    2.00    --  107.00 -93.00 120.00   82
 82  \w     43.00  70.00   0.50    2.00    --  107.00-133.00 -90.00   54
 83  \w     42.00  68.00   0.50    2.00    --  107.00-111.00 -30.00   52
 84  \w     49.00  75.00   0.50    2.00    --  107.00-133.00 -30.00   52
 85  \w     40.00  93.00   0.50    2.00    --  107.00 -37.00  90.00  106
 86  \w     38.00  64.00   0.50    2.00    --  107.00-111.00 -90.00   52
 87  \w     74.00 100.00   0.50    2.00    --  107.00-111.00 -90.00   52
 88  \w     38.00  83.00   0.50    2.00    --  107.00 -93.00  60.00   90
 89  \w     78.00 104.00   0.50    2.00    --  107.00-111.00   0.00   52
 90  \w    104.00 131.00   0.50    2.00    --  107.00  30.00-120.00   54
 91  \w     78.00 104.00   0.50    2.00    --  107.00-133.00 -90.00   52
 92  \w    102.00 128.00   0.50    2.00    --  107.00 -61.00 120.00   52
 93  \w     67.00 115.00   0.50    2.00    --  107.00 -61.00 -30.00   96
 94  \w     55.00  98.00   0.50    2.00    --  107.00 -61.00 120.00   86
 95  \w    126.00 152.00   0.50    2.00    --  107.00 106.00 140.00   52
 96  \w    -43.00 -18.00   0.50    0.50    --    4.00 119.00 -32.21   50
 97  \w    -26.00   2.00   0.50    0.50    --   20.00 118.00 118.91   56
 98  \w    -50.00 -25.00   0.50    0.50    --   24.00 164.00 -48.58   50
 99  \w     -7.00  19.00   0.50    0.50    --   28.00  99.00  57.14   52
100  \w     -8.00  17.00   0.50    0.50    --   28.00 100.00 -68.89   50
101  \w      1.00  26.00   0.50    0.50    --   32.00  89.00 -15.22   50
102  \w    -75.00 -49.00   0.50    0.50    --  -38.82 104.00-150.00   52
103  \w      9.00  34.00   0.50    0.50    --   38.82  85.00  -1.11   50
104  \w     11.00  36.00   0.50    0.50    --   40.00  83.00-175.59   50
105  \w     11.00  36.00   0.50    0.50    --   40.00  84.00 145.35   50
106  \w     16.00  41.00   0.50    0.50    --   44.00  81.00 125.05   50
107  \w     16.00  41.00   0.50    0.50    --   44.00  81.00 -79.62   50
108  \w     19.00  44.00   0.50    0.50    --   44.00  81.00 161.16   50
109  \w     16.00  41.00   0.50    0.50    --   44.00  82.00 -62.27   50
110  \w     16.00  41.00   0.50    0.50    --   44.00  80.00  38.10   50
111  \w     16.00  41.00   0.50    0.50    --   44.00  81.00-145.03   50
112  \w     16.00  41.00   0.50    0.50    --   44.00  82.00 -22.42   50
113  \w     26.00  52.00   0.50    0.50    --   52.00  76.00-158.25   52
114  \w     25.00  50.00   0.50    0.50    --   52.00  77.00 -48.86   50
115  \w     27.00  58.00   0.50    0.50    --   52.00  72.00 117.40   62
116  \w     29.00  55.00   0.50    0.50    --   52.00  75.00   4.36   52
117  \w     95.00 121.00   0.50    0.50    --   56.00  75.00-108.02   52
118  \w     30.00  56.00   0.50    0.50    --   56.00  75.00-108.02   52
119  \w     33.00  59.00   0.50    0.50    --   56.00  68.00  74.32   52
120  \w     97.00 123.00   0.50    0.50    --   60.00  77.00 -23.41   52
121  \w     34.00  63.00   0.50    0.50    --   60.00  75.00  90.41   58
122  \w     35.00  66.00   0.50    0.50    --   60.00  70.00  43.46   62
123  \w     33.00  58.00   0.50    0.50    --   60.00  77.00 -23.41   50
124  \w     39.00  64.00   0.50    0.50    --   64.00  70.00  17.54   50
125  \w     85.00 111.00   0.50    0.50    --   64.00  69.00 -76.21   52
126  \w     40.00  66.00   0.50    0.50    --   64.00  69.00 -76.21   52
127  \w     38.00  64.00   0.50    0.50    --   64.00  77.00-137.53   52
128  \w    108.00 133.00   0.50    0.50    --   68.00  56.00 127.97   50
129  \w     53.00  79.00   0.50    0.50    --   68.00  56.00 127.97   52
130  \w     46.00  89.00   0.50    0.50    --   72.00  77.00 -57.21   86
131  \w     48.00  95.00   0.50    0.50    --   72.00  67.00  89.25   94
132  \w     48.00  86.00   0.50    0.50    --   72.00  67.00-148.41   76
133  \w     48.00  74.00   0.50    0.50    --   72.00  71.00-113.35   52
134  \w     55.00  80.00   0.50    2.00    --   80.00  72.00 145.23   50
135  \w     55.00  81.00   0.50    2.00    --   80.00  76.00 -22.21   52
136  \w     54.00  80.00   0.50    2.00    --   80.00  76.00 118.39   52
137  \w     57.00  99.00   0.50    2.00    --   84.00  77.00 166.12   84
138  \w     58.00 103.00   0.50    2.00    --   84.00  75.00  25.39   90
139  \w     59.00  85.00   0.50    2.00    --   84.00  70.00   8.61   52
140  \w     57.00  85.00   0.50    2.00    --   84.00  77.00 -38.14   56
141  \w     58.00 115.00   0.50    2.00    --   84.00  74.00  53.07  114
142  \w     59.00  85.00   0.50    2.00    --   84.00  70.00 -83.65   52
143  \w     67.00  93.00   0.50    2.00    --   88.00  62.00-116.49   52
144  \w     69.00  95.00   0.50    2.00    --   92.00  67.00 152.24   52
145  \w     75.00 119.00   0.50    2.00    --  100.00  70.00-167.54   88
146  \w    124.00 150.00   0.50    2.00    --  100.00  72.00 168.99   52
147  \w     75.00 101.00   0.50    2.00    --  100.00  72.00 168.99   52
148  \w     35.00  99.00   0.50    2.00    --  107.00 -22.00-180.00  128
149  \w     85.00 111.00   0.50    2.00    --  107.00  61.00  30.00   52
150  \w     86.00 153.00   0.50    2.00    --  107.00  61.00 -60.00  134
151  \w    130.00 156.00   0.50    2.00    --  107.00  77.00 -30.00   52
152  \w    131.00 157.00   0.50    2.00    --  107.00  69.00   0.00   52
153  \w    118.00 151.00   0.50    2.00    --  107.00  77.00-150.00   66
154  \w     80.00 113.00   0.50    2.00    --  107.00  77.00-150.00   66
155  \w     80.00 118.00   0.50    2.00    --  107.00  77.00 -30.00   76
156  \w     44.00  70.00   0.50    2.00    --  107.00 -93.00-150.00   52
157  \w     83.00 113.00   0.50    2.00    --  107.00  69.00   0.00   60
158  \w     85.00 157.00   0.50    2.00    --  107.00  66.00 -32.21  144
159  \w    126.00 155.00   0.50    2.00    --  107.00  77.00 -90.00   58
160  \w     42.00  88.00   0.50    2.00    --  107.00 -30.00  30.00   92
161  \w     80.00 116.00   0.50    2.00    --  107.00  77.00 -90.00   72
162  \w    129.00 154.00   0.50    2.00    --  107.00  61.00 -90.00   50
163  \w     85.00 119.00   0.50    2.00    --  107.00  61.00 -90.00   68
164  \w     83.00 108.00   0.50    2.00    --  107.00  69.00  30.00   50
165  \w    120.00 157.00   0.50    2.00    --  107.00  77.00 -60.00   74
166  \w     84.00 142.00   0.50    2.00    --  107.00  69.00-120.00  116
167  \w     57.00 107.00   0.50    2.00    --  107.00 -45.00  30.00  100
168  \w     80.00 114.00   0.50    2.00    --  107.00  77.00 -60.00   68
;
_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      -0.0840364000
_diffrn_orient_matrix_UB_12      -0.0716208000
_diffrn_orient_matrix_UB_13      -0.0009510000
_diffrn_orient_matrix_UB_21      0.0076594000
_diffrn_orient_matrix_UB_22      0.0764419000
_diffrn_orient_matrix_UB_23      0.0767114000
_diffrn_orient_matrix_UB_31      -0.0220808000
_diffrn_orient_matrix_UB_32      0.2998312000
_diffrn_orient_matrix_UB_33      -0.0197484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32654
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.980
_diffrn_reflns_theta_min         3.099
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42855
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0686P)^2^+0.5654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3057
_reflns_number_total             3399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01634_si_003.cif
_cod_data_source_block           10681-12188_cat9-115
_cod_original_cell_volume        1687.68(5)
_cod_database_code               4033880
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'c20 o4 n3'
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.674
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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), C16(H16), C7(H7), C10(H10), C17(H17), C20(H20), C19(H19), C18(H18)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              6181
_shelx_hkl_checksum              53673
_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 2.606
_oxdiff_exptl_absorpt_empirical_full_min 0.514