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_4033882
_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         'C24 H18 Br N O2, C2 H3 N'
_chemical_formula_sum            'C26 H21 Br N2 O2'
_chemical_formula_weight         473.36
_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             2019-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                93.9200(10)
_cell_angle_beta                 95.1410(10)
_cell_angle_gamma                106.4740(10)
_cell_formula_units_Z            4
_cell_length_a                   10.11970(10)
_cell_length_b                   10.50710(10)
_cell_length_c                   21.9497(2)
_cell_measurement_reflns_used    15645
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.5530
_cell_measurement_theta_min      2.0200
_cell_volume                     2218.30(4)
_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_temperature      100(2)
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -22.00  41.00   0.50    0.20    --   38.82 -90.00-173.00  126
  2  \w     81.00 108.00   0.50    0.42    --  107.00  90.00 -59.00   54
  3  \w    117.00 143.00   0.50    0.42    --  107.00  90.00 -59.00   52
  4  \w     98.00 130.00   0.50    0.42    --  107.00 -90.00-173.00   64
  5  \w    -21.00  17.00   0.50    0.20    --  -38.82 104.00   0.00   76
  6  \w    -63.00 -20.00   0.50    0.20    --  -38.82 104.00-180.00   86
  7  \w     -8.00  27.00   0.50    0.20    --  -38.82  43.00 120.00   70
  8  \w    -51.00  30.00   0.50    0.20    --  -38.82  32.00 -90.00  162
  9  \w    -59.00 -16.00   0.50    0.20    --  -38.82  77.00 -30.00   86
 10  \w    -69.00 -32.00   0.50    0.20    --  -38.82  90.00 -59.00   74
 11  \w    -66.00 -28.00   0.50    0.20    --  -38.82 104.00   0.00   76
 12  \w    -97.00 -52.00   0.50    0.20    --  -38.82 138.00  60.00   90
 13  \w    -10.00  15.00   0.50    0.20    --  -38.82 104.00-180.00   50
 14  \w    -53.00 -27.00   0.50    0.20    --  -38.82  43.00 120.00   52
 15  \w     -1.00  28.00   0.50    0.20    --  -38.82  77.00 -30.00   58
 16  \w     23.00  62.00   0.50    0.20    --   38.82  43.00   0.00   78
 17  \w     19.00  60.00   0.50    0.20    --   38.82  65.00 120.00   82
 18  \w     20.00  54.00   0.50    0.20    --   38.82 -65.00  90.00   68
 19  \w     25.00 103.00   0.50    0.20    --   38.82  65.00 -90.00  156
 20  \w     20.00 102.00   0.50    0.20    --   38.82  54.00  60.00  164
 21  \w     26.00  51.00   0.50    0.20    --   38.82  54.00 -60.00   50
 22  \w     36.00  61.00   0.50    0.20    --   38.82-104.00-180.00   50
 23  \w    -16.00  19.00   0.50    0.20    --   38.82-104.00-180.00   70
 24  \w     58.00 103.00   0.50    0.20    --   38.82  54.00 -60.00   90
 25  \w    -28.00  19.00   0.50    0.20    --   38.82 -77.00   0.00   94
 26  \w     40.00  66.00   0.50    0.20    --   38.82 -77.00   0.00   52
 27  \w     66.00 104.00   0.50    0.20    --   38.82  43.00   0.00   76
 28  \w     12.00  39.00   0.50    0.20    --   38.82 -32.00-180.00   54
 29  \w     17.00  42.00   0.50    0.20    --   38.82 -32.00 -60.00   50
 30  \w    -30.00  11.00   0.50    0.20    --   38.82 -32.00-180.00   82
 31  \w     71.00  96.00   0.50    0.20    --   38.82  32.00 -60.00   50
 32  \w     65.00  91.00   0.50    0.20    --   38.82  65.00 120.00   52
 33  \w     72.00  97.00   0.50    0.20    --   38.82-138.00  60.00   50
 34  \w    -26.00  15.00   0.50    0.20    --   38.82 -65.00  90.00   82
 35  \w    -23.00   2.00   0.50    0.20    --   38.82 -32.00 -60.00   50
 36  \w     98.00 137.00   0.50    0.42    --  107.00 111.00 -30.00   78
 37  \w     44.00  77.00   0.50    0.42    --  107.00-133.00 120.00   66
 38  \w    119.00 157.00   0.50    0.42    --  107.00  30.00 -30.00   76
 39  \w     43.00 123.00   0.50    0.42    --  107.00-133.00-120.00  160
 40  \w    125.00 151.00   0.50    0.42    --  107.00  93.00 -90.00   52
 41  \w     93.00 156.00   0.50    0.42    --  107.00  30.00-150.00  126
 42  \w     93.00 153.00   0.50    0.42    --  107.00  22.00 -90.00  120
 43  \w     97.00 123.00   0.50    0.42    --  107.00  93.00 -90.00   52
 44  \w    100.00 152.00   0.50    0.42    --  107.00  22.00  60.00  104
 45  \w     38.00 118.00   0.50    0.42    --  107.00 -30.00   0.00  160
 46  \w     87.00 123.00   0.50    0.42    --  107.00-133.00-180.00   72
 47  \w     39.00  77.00   0.50    0.42    --  107.00 -30.00 150.00   76
 48  \w     81.00 157.00   0.50    0.42    --  107.00  93.00 120.00  152
 49  \w     67.00  93.00   0.50    0.42    --  107.00 -93.00 120.00   52
 50  \w     42.00 129.00   0.50    0.42    --  107.00 -61.00-180.00  174
 51  \w     33.00  60.00   0.50    0.42    --  107.00 -93.00 120.00   54
 52  \w     53.00  91.00   0.50    0.42    --  107.00 -37.00-180.00   76
 53  \w     43.00 109.00   0.50    0.42    --  107.00-133.00  30.00  132
 54  \w     49.00 123.00   0.50    0.42    --  107.00-133.00  90.00  148
 55  \w     41.00  86.00   0.50    0.42    --  107.00 -69.00  60.00   90
 56  \w     85.00 153.00   0.50    0.42    --  107.00  69.00 150.00  136
 57  \w     59.00  85.00   0.50    0.42    --  107.00-133.00-180.00   52
 58  \w     47.00 123.00   0.50    0.42    --  107.00-133.00   0.00  152
 59  \w     34.00  68.00   0.50    0.42    --  107.00 -93.00-180.00   68
 60  \w     78.00 106.00   0.50    0.42    --  107.00 -93.00-180.00   56
 61  \w     77.00 120.00   0.50    0.42    --  107.00 -30.00 -90.00   86
 62  \w     98.00 147.00   0.50    0.42    --  107.00  15.00 120.00   98
 63  \w     94.00 156.00   0.50    0.42    --  107.00  45.00 -60.00  124
 64  \w     43.00 124.00   0.50    0.42    --  107.00 -77.00 120.00  162
 65  \w     82.00 108.00   0.50    0.42    --  107.00-133.00 120.00   52
 66  \w     60.00  99.00   0.50    0.42    --  107.00 -93.00  60.00   78
 67  \w     47.00  85.00   0.50    0.42    --  107.00 -93.00   0.00   76
 68  \w     96.00 121.00   0.50    0.42    --  107.00 -30.00 150.00   50
 69  \w     43.00  98.00   0.50    0.42    --  107.00 -53.00 -30.00  110
 70  \w    113.00 155.00   0.50    0.42    --  107.00  90.00 -59.00   84
 71  \w    -46.00 -15.00   0.50    0.20    --    0.00 124.00 -50.15   62
 72  \w    -19.00   6.00   0.50    0.20    --   24.00 113.00 172.24   50
 73  \w    -10.00  15.00   0.50    0.20    --   28.00 104.00  75.69   50
 74  \w     -8.00  17.00   0.50    0.20    --   28.00 100.00 -92.32   50
 75  \w     -1.00  24.00   0.50    0.20    --   32.00  93.00  12.94   50
 76  \w      6.00  31.00   0.50    0.20    --   36.00  87.00-163.59   50
 77  \w      5.00  30.00   0.50    0.20    --   36.00  88.00 -79.91   50
 78  \w      6.00  31.00   0.50    0.20    --   36.00  87.00  28.74   50
 79  \w      5.00  30.00   0.50    0.20    --   36.00  88.00  96.13   50
 80  \w      5.00  30.00   0.50    0.20    --   36.00  89.00 141.51   50
 81  \w    -26.00  23.00   0.50    0.20    --  -38.82  54.00 -60.00   98
 82  \w    -53.00 -27.00   0.50    0.20    --  -38.82  54.00 -60.00   52
 83  \w    -63.00 -37.00   0.50    0.20    --  -38.82 138.00  30.00   52
 84  \w     12.00  37.00   0.50    0.20    --   40.00  82.00 -31.94   50
 85  \w     11.00  36.00   0.50    0.20    --   40.00  84.00-110.96   50
 86  \w     16.00  41.00   0.50    0.20    --   44.00  82.00  40.95   50
 87  \w     16.00  41.00   0.50    0.20    --   44.00  81.00-178.90   50
 88  \w     16.00  41.00   0.50    0.20    --   44.00  82.00  82.88   50
 89  \w     16.00  41.00   0.50    0.20    --   44.00  82.00 122.10   50
 90  \w     16.00  41.00   0.50    0.20    --   44.00  81.00  -1.61   50
 91  \w     16.00  41.00   0.50    0.20    --   44.00  81.00-133.60   50
 92  \w     33.00  59.00   0.50    0.20    --   52.00  77.00-123.68   52
 93  \w     25.00  51.00   0.50    0.20    --   52.00  77.00-165.54   52
 94  \w     28.00  54.00   0.50    0.20    --   52.00  74.00 -66.33   52
 95  \w     26.00  52.00   0.50    0.20    --   52.00  77.00  41.82   52
 96  \w     26.00  52.00   0.50    0.20    --   52.00  75.00 -31.28   52
 97  \w     33.00  59.00   0.50    0.20    --   56.00  74.00 -90.80   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26883
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.029
_diffrn_reflns_theta_min         2.031
_exptl_absorpt_coefficient_mu    2.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41821
_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    1.417
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.970
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.00026(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         8919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0597P)^2^+0.3596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7972
_reflns_number_total             8919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01634_si_005.cif
_cod_data_source_block           10681-12188_cat8-151
_cod_database_code               4033882
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.467
_shelx_estimated_absorpt_t_min   0.401
_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, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H3SD)=Sof(H3SE)=Sof(H3SF)=Sof(N1SS)=Sof(C2SS)=1-FVAR(1)
 Sof(N1S)=Sof(H3SA)=Sof(H3SB)=Sof(H3SC)=Sof(C2S)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N1B(H1B), C17B(H17B), C15(H15), C14(H14), C10B(H10B), C18B(H18B),
 C18(H18), C17(H17), C14B(H14B), C24(H24), C20(H20), C15B(H15B), C22(H22),
 C23(H23), C9B(H9B), C6(H6), C6B(H6B), C10(H10), C24B(H24B), C8(H8), C9(H9),
 C20B(H20B), C23B(H23B), C7(H7), C21(H21), C8B(H8B), C21B(H21B), C7B(H7B),
 C22B(H22B)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12B(H12D,H12E,H12F), C3SB(H3SG,H3SH,H3SI), C3S(H3SA,
 H3SB,H3SC), C3S(H3SD,H3SE,H3SF)
;
_shelx_res_checksum              17504
_shelx_hkl_checksum              67413
_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
;