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_4033881
_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         'C28 H20 Cl N3 O3'
_chemical_formula_sum            'C28 H20 Cl N3 O3'
_chemical_formula_weight         481.92
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.7343(10)
_cell_length_b                   7.6126(2)
_cell_length_c                   27.7175(8)
_cell_measurement_reflns_used    5814
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.0520
_cell_measurement_theta_min      3.1700
_cell_volume                     5430.0(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 0.992
_diffrn_measured_fraction_theta_max 0.975
_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    -12.00  28.00   0.50    1.84    --  -38.95  88.00-130.00   80
  2  \w    -61.00 -35.00   0.50    1.84    --  -38.95  88.00-130.00   52
  3  \w    -44.00  21.00   0.50    1.84    --  -38.95  34.00  56.00  130
  4  \w   -103.00 -63.00   0.50    1.84    --  -38.95 -34.00-100.00   80
  5  \w    -76.00 -51.00   0.50    1.84    --  -38.95 148.00 -77.00   50
  6  \w      4.00  29.00   0.50    1.84    --   38.95-123.00  38.00   50
  7  \w     26.00  67.00   0.50    1.84    --   38.95  34.00  56.00   82
  8  \w     38.00  64.00   0.50    1.84    --   38.95-148.00-125.00   52
  9  \w      6.00  62.00   0.50    1.84    --   38.95 -88.00 112.00  112
 10  \w    132.00 157.00   0.50    7.38    --  107.00 123.00 118.00   50
 11  \w     39.00  91.00   0.50    7.38    --  107.00 -88.00 112.00  104
 12  \w     76.00 109.00   0.50    7.38    --  107.00 123.00 118.00   66
 13  \w     80.00 120.00   0.50    7.38    --  107.00 -34.00-100.00   80
 14  \w    118.00 152.00   0.50    7.38    --  107.00  88.00-130.00   68
 15  \w    101.00 156.00   0.50    7.38    --  107.00  34.00  56.00  110
 16  \w     42.00  78.00   0.50    7.38    --  107.00-148.00-125.00   72
 17  \w    -60.00 -11.00   0.50    1.84    --  -38.95 138.00-120.00   98
 18  \w    -45.00 -20.00   0.50    1.84    --  -38.95 123.00 118.00   50
 19  \w      0.00  25.00   0.50    1.84    --   38.95 -34.00-100.00   50
 20  \w     12.00 101.00   0.50    1.84    --   38.95  77.00 150.00  178
 21  \w     82.00 107.00   0.50    1.84    --   38.95  32.00 -30.00   50
 22  \w     45.00  98.00   0.50    1.84    --   38.95  43.00-120.00  106
 23  \w     56.00  82.00   0.50    1.84    --   38.95  32.00-120.00   52
 24  \w     95.00 149.00   0.50    7.38    --  107.00  37.00-150.00  108
 25  \w     47.00 120.00   0.50    7.38    --  107.00-133.00 -30.00  146
 26  \w     88.00 156.00   0.50    7.38    --  107.00  69.00  30.00  136
 27  \w     74.00 111.00   0.50    7.38    --  107.00-111.00 120.00   74
 28  \w     42.00  68.00   0.50    7.38    --  107.00-111.00 120.00   52
 29  \w     92.00 155.00   0.50    7.38    --  107.00  77.00 120.00  126
 30  \w    -16.00  10.00   0.50    1.84    --   38.95 -34.00-100.00   52
 31  \w   -104.00 -79.00   0.50    1.84    --  -38.95 -65.00 150.00   50
 32  \w    -43.00 -17.00   0.50    1.84    --  -38.95 -65.00 150.00   52
 33  \w    -13.00  27.00   0.50    1.84    --  -38.95  32.00-120.00   80
 34  \w    -19.00   7.00   0.50    1.84    --   38.95 -32.00 120.00   52
 35  \w     92.00 149.00   0.50    7.38    --  107.00 111.00-120.00  114
 36  \w     81.00 157.00   0.50    7.38    --  107.00  93.00  90.00  152
 37  \w     54.00  60.00   0.50    7.38    --  107.00 -30.00   0.00   12
;
_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      -0.0114177000
_diffrn_orient_matrix_UB_12      -0.0823634000
_diffrn_orient_matrix_UB_13      -0.0496461000
_diffrn_orient_matrix_UB_21      -0.0585177000
_diffrn_orient_matrix_UB_22      0.0328463000
_diffrn_orient_matrix_UB_23      0.0074919000
_diffrn_orient_matrix_UB_31      0.0054548000
_diffrn_orient_matrix_UB_32      0.1818907000
_diffrn_orient_matrix_UB_33      -0.0238387000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            23136
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.564
_diffrn_reflns_theta_min         3.189
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86746
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       plate
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0648
_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^)+(0.0570P)^2^+4.9660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4131
_reflns_number_total             5425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01634_si_004.cif
_cod_data_source_block           10681-12188_cat9-17
_cod_database_code               4033881
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C28 N3 O3 Cl'
_shelx_estimated_absorpt_t_max   0.864
_shelx_estimated_absorpt_t_min   0.743
_reflns_odcompleteness_completeness 98.92
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C20(H20), C19(H19), C16(H16), C17(H17), C8(H8), C7(H7), C24(H24),
 C28(H28), C13(H13), C25(H25), C27(H27), C26(H26), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              68928
_shelx_hkl_checksum              97090
_shelx_fab_checksum              85975
_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 2.907
_oxdiff_exptl_absorpt_empirical_full_min 0.573