Fe(II)-Catalyzed Isomerization of 4-Vinylisoxazoles into Pyrroles.
Galenko, Ekaterina E.; Bodunov, Vladimir A.; Galenko, Alexey V.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; The Journal of organic chemistry 82 (2017) 8568–8579; doi:10.1021/acs.joc.7b01351

data_4032723
_publ_section_title
;
 Fe(II)-Catalyzed Isomerization of 4-Vinylisoxazoles into Pyrroles.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8568
_journal_page_last               8579
_journal_paper_doi               10.1021/acs.joc.7b01351
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C18 H13 Br N2 O4'
_chemical_formula_sum            'C18 H13 Br N2 O4'
_chemical_formula_weight         401.21
_chemical_name_systematic
'Methyl 2-(4-bromophenyl)-5-(4-nitrophenyl)-1H-pyrrole-3-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-16
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.573(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0919(10)
_cell_length_b                   7.0413(3)
_cell_length_c                   13.4921(9)
_cell_measurement_reflns_used    5575
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.8020
_cell_measurement_theta_min      3.1370
_cell_volume                     1598.37(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details
;
  1 omega  -82.00    2.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000 -120.0000 84

  2 omega  -99.00  -61.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000 -150.0000 38

  3 omega  -87.00   29.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241    0.0000   30.0000 116

  4 omega   -3.00   93.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -180.0000 96

  5 omega   74.00   99.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  178.0000 -120.0000 25

  6 omega  -25.00   65.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   60.0000 90

  7 omega  -60.00  -10.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  -30.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0066873000
_diffrn_orient_matrix_UB_12      0.0992296000
_diffrn_orient_matrix_UB_13      0.0003883000
_diffrn_orient_matrix_UB_21      -0.0415497000
_diffrn_orient_matrix_UB_22      -0.0162614000
_diffrn_orient_matrix_UB_23      -0.0178177000
_diffrn_orient_matrix_UB_31      0.0025852000
_diffrn_orient_matrix_UB_32      -0.0061262000
_diffrn_orient_matrix_UB_33      0.0536399000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17370
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.861
_diffrn_reflns_theta_min         3.020
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_preparation       'See experimental part'
_exptl_crystal_recrystallization_method
'Was obtained by slow evaporation from acetonitrile'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0290P)^2^+0.7310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3966
_reflns_number_total             4617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01351_si_002.cif
_cod_data_source_block           103-7060-5830_cat_5_79
_cod_original_cell_volume        1598.36(17)
_cod_database_code               4032723
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'Br N2 O4 C17'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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:
 C13(H13), N1(H1), C7(H7), C18(H18), C17(H17), C6(H6), C10(H10), C16(H16),
 C14(H14), C9(H9)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              77603
_shelx_hkl_checksum              28472
_olex2_submission_special_instructions 'No special instructions were received'