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_4033883
_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         'C18 H13 Cl N2 O2'
_chemical_formula_sum            'C18 H13 Cl N2 O2'
_chemical_formula_weight         324.75
_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                109.196(2)
_cell_angle_beta                 95.169(2)
_cell_angle_gamma                96.0440(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2140(2)
_cell_length_b                   9.26000(10)
_cell_length_c                   9.6732(2)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.4750
_cell_measurement_theta_min      4.8480
_cell_volume                     768.25(3)
_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 0.990
_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    -26.00   0.00   0.50    0.20    --  -38.82 106.00 121.00   52
  2  \w     -2.00  78.00   0.50    0.20    --   38.82-106.00  21.00  160
  3  \w     79.00 105.00   0.50    0.20    --  107.00-106.00  21.00   52
  4  \w    104.00 130.00   0.50    0.20    --  107.00 106.00 121.00   52
  5  \w   -111.00 -64.00   0.50    0.20    --  -38.82 -21.00 -60.00   94
  6  \w   -104.00 -20.00   0.50    0.20    --  -38.82 -77.00  90.00  168
  7  \w   -101.00 -74.00   0.50    0.20    --  -38.82 -77.00 120.00   54
  8  \w    -64.00  18.00   0.50    0.20    --  -38.82  77.00-120.00  164
  9  \w    -49.00 -19.00   0.50    0.20    --  -38.82  77.00  30.00   60
 10  \w    -46.00 -21.00   0.50    0.20    --  -38.82 -21.00 -60.00   50
 11  \w    -63.00 -14.00   0.50    0.20    --  -38.82 -77.00 120.00   98
 12  \w   -107.00 -82.00   0.50    0.20    --  -38.82 -32.00   0.00   50
 13  \w    -16.00  28.00   0.50    0.20    --  -38.82  77.00  30.00   88
 14  \w    -80.00 -55.00   0.50    0.20    --  -38.82 -32.00   0.00   50
 15  \w     80.00 105.00   0.50    0.20    --   38.82  43.00 -30.00   50
 16  \w     30.00  99.00   0.50    0.20    --   38.82  54.00  90.00  138
 17  \w     66.00  99.00   0.50    0.20    --   38.82  54.00-120.00   66
 18  \w     28.00  74.00   0.50    0.20    --   38.82  32.00-150.00   92
 19  \w     20.00  61.00   0.50    0.20    --   38.82  54.00-120.00   82
 20  \w     80.00 108.00   0.50    0.20    --   38.82  32.00-150.00   56
 21  \w     26.00  52.00   0.50    0.20    --   38.82  43.00 -30.00   52
 22  \w     12.00  48.00   0.50    0.20    --   38.82-138.00   0.00   72
 23  \w     78.00 103.00   0.50    0.20    --   38.82  32.00 -60.00   50
 24  \w     -2.00  23.00   0.50    0.20    --   38.82 -65.00-120.00   50
 25  \w     54.00  86.00   0.50    0.20    --   38.82-138.00   0.00   64
 26  \w     36.00  62.00   0.50    0.20    --   38.82 -65.00-120.00   52
 27  \w     63.00  95.00   0.50    0.20    --   38.82-138.00 -90.00   64
 28  \w     90.00 156.00   0.50    0.20    --  107.00  45.00 120.00  132
 29  \w    102.00 148.00   0.50    0.20    --  107.00  45.00 -90.00   92
 30  \w     44.00 108.00   0.50    0.20    --  107.00-133.00   0.00  128
 31  \w     84.00 110.00   0.50    0.20    --  107.00-111.00-180.00   52
 32  \w     91.00 117.00   0.50    0.20    --  107.00 -22.00 -60.00   52
 33  \w     92.00 117.00   0.50    0.20    --  107.00  37.00  60.00   50
 34  \w     47.00 111.00   0.50    0.20    --  107.00-111.00   0.00  128
 35  \w     35.00  69.00   0.50    0.20    --  107.00 -22.00 -60.00   68
 36  \w     44.00 127.00   0.50    0.20    --  107.00 -53.00 -30.00  166
 37  \w    103.00 157.00   0.50    0.20    --  107.00  93.00 -90.00  108
 38  \w     59.00 115.00   0.50    0.20    --  107.00 -37.00-180.00  112
 39  \w     87.00 119.00   0.50    0.20    --  107.00-133.00-180.00   64
 40  \w     89.00 131.00   0.50    0.20    --  107.00  93.00 -60.00   84
 41  \w     48.00  83.00   0.50    0.20    --  107.00-133.00-180.00   70
 42  \w     90.00 131.00   0.50    0.20    --  107.00  45.00  90.00   82
 43  \w     45.00  75.00   0.50    0.20    --  107.00 -93.00 120.00   60
 44  \w     83.00 137.00   0.50    0.20    --  107.00 -86.00 150.00  108
 45  \w     96.00 132.00   0.50    0.20    --  107.00 -69.00 -30.00   72
 46  \w     42.00  89.00   0.50    0.20    --  107.00 -69.00 -30.00   94
 47  \w     44.00  80.00   0.50    0.20    --  107.00 -86.00 150.00   72
 48  \w     99.00 144.00   0.50    0.20    --  107.00  30.00-180.00   90
 49  \w     37.00 103.00   0.50    0.20    --  107.00 -93.00  60.00  132
 50  \w     72.00 122.00   0.50    0.20    --  107.00-133.00 -30.00  100
 51  \w     55.00 116.00   0.50    0.20    --  107.00 -45.00-120.00  122
 52  \w    132.00 157.00   0.50    0.20    --  107.00  37.00  60.00   50
 53  \w     53.00 120.00   0.50    0.20    --  107.00 -37.00  90.00  134
 54  \w    107.00 144.00   0.50    0.20    --  107.00  61.00-150.00   74
 55  \w    118.00 153.00   0.50    0.20    --  107.00  61.00-180.00   70
 56  \w     42.00 108.00   0.50    0.20    --  107.00 -61.00 150.00  132
 57  \w     88.00 119.00   0.50    0.20    --  107.00  53.00-120.00   62
 58  \w     94.00 119.00   0.50    0.20    --  107.00 106.00 121.00   50
 59  \w    -41.00 -11.00   0.50    0.20    --    4.00 116.00 113.80   60
 60  \w    -21.00   4.00   0.50    0.20    --   24.00 116.00-170.72   50
 61  \w     -8.00  17.00   0.50    0.20    --   28.00 100.00 -62.00   50
 62  \w      1.00  26.00   0.50    0.20    --   32.00  88.00 -60.16   50
 63  \w     -1.00  24.00   0.50    0.20    --   32.00  94.00  10.28   50
 64  \w      0.00  25.00   0.50    0.20    --   32.00  91.00  63.29   50
 65  \w      7.00  32.00   0.50    0.20    --   36.00  84.00-134.88   50
 66  \w      4.00  29.00   0.50    0.20    --   36.00  90.00 119.26   50
 67  \w      5.00  30.00   0.50    0.20    --   36.00  88.00 -23.89   50
 68  \w    -60.00   4.00   0.50    0.20    --  -38.82  77.00 120.00  128
 69  \w     10.00  35.00   0.50    0.20    --   38.82  83.00-163.45   50
 70  \w     30.00  56.00   0.50    0.20    --   38.82 -54.00  90.00   52
 71  \w      0.00  34.00   0.50    0.20    --   38.82 -32.00  30.00   68
 72  \w     12.00  37.00   0.50    0.20    --   40.00  82.00-112.27   50
 73  \w     13.00  38.00   0.50    0.20    --   40.00  79.00 -58.16   50
 74  \w     11.00  36.00   0.50    0.20    --   40.00  84.00  27.13   50
 75  \w     16.00  41.00   0.50    0.20    --   44.00  81.00 157.46   50
 76  \w     16.00  41.00   0.50    0.20    --   44.00  82.00   7.61   50
 77  \w     16.00  41.00   0.50    0.20    --   44.00  81.00 -36.18   50
 78  \w     16.00  41.00   0.50    0.20    --   44.00  81.00  94.40   50
 79  \w     21.00  46.00   0.50    0.20    --   48.00  77.00-102.07   50
 80  \w     28.00  46.00   0.50    0.20    --   52.00  72.00   2.02   36
;
_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      0.0520394000
_diffrn_orient_matrix_UB_12      0.0216073000
_diffrn_orient_matrix_UB_13      0.1623372000
_diffrn_orient_matrix_UB_21      0.1559416000
_diffrn_orient_matrix_UB_22      0.0646719000
_diffrn_orient_matrix_UB_23      -0.0166806000
_diffrn_orient_matrix_UB_31      -0.0418337000
_diffrn_orient_matrix_UB_32      0.1644237000
_diffrn_orient_matrix_UB_33      0.0481408000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7503
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.787
_diffrn_reflns_theta_min         4.870
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74094
_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    1.404
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0645P)^2^+0.3152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2983
_reflns_number_total             3086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01634_si_002.cif
_cod_data_source_block           10681-12188_cat8-147
_cod_database_code               4033883
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C18 Cl N2 O2'
_shelx_estimated_absorpt_t_max   0.644
_shelx_estimated_absorpt_t_min   0.468
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C7(H7), C10(H10), C18(H18), C17(H17), C14(H14), C16(H16),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              50074
_shelx_hkl_checksum              13591
_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 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.734