Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2 H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads.
Mikhailov, Kirill I.; Galenko, Ekaterina E.; Galenko, Alexey V.; Novikov, Mikhail S.; Ivanov, Alexander Yu; Starova, Galina L.; Khlebnikov, Alexander F.; The Journal of organic chemistry 83 (2018) 3177–3187; doi:10.1021/acs.joc.8b00069

data_4035167
_publ_section_title
;
 Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2
 H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of
 Pyrazole-Nitrogen Heterocycle Dyads.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3177
_journal_page_last               3187
_journal_paper_doi               10.1021/acs.joc.8b00069
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C12 H9 N3 O'
_chemical_formula_sum            'C12 H9 N3 O'
_chemical_formula_weight         211.22
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-04-19
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
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_cell_angle_alpha                90
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_cell_length_b                   14.0379(6)
_cell_length_c                   10.8986(5)
_cell_measurement_reflns_used    2233
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6430
_cell_measurement_theta_min      5.1660
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
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_diffrn_detector_area_resol_mean 10.3829
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_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -49.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -120.0000 82

  2 omega   -7.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000  -30.0000 36

  3 omega  -41.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 55

  4 omega   71.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   60.0000 59

  5 omega   84.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 92

  6 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 26

  7 omega   66.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 34

  8 omega   62.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 29

  9 omega   40.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 75

 10 omega   45.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 52

 11 omega   63.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 70

 12 omega  102.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 60

 13 omega   36.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 55

 14 omega   -9.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -180.0000 28

 15 omega -111.00  -61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000 -180.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0233753000
_diffrn_orient_matrix_UB_12      0.0964421000
_diffrn_orient_matrix_UB_13      -0.0636868000
_diffrn_orient_matrix_UB_21      0.0770281000
_diffrn_orient_matrix_UB_22      -0.0517455000
_diffrn_orient_matrix_UB_23      -0.1083039000
_diffrn_orient_matrix_UB_31      -0.2197209000
_diffrn_orient_matrix_UB_32      -0.0078651000
_diffrn_orient_matrix_UB_33      -0.0684890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
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_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
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_diffrn_reflns_theta_max         69.955
_diffrn_reflns_theta_min         5.178
_diffrn_source                   'sealed X-ray tube'
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_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
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_exptl_crystal_description
;
;
_exptl_crystal_F_000             440
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_refine_diff_density_max         0.229
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.2486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1638
_reflns_number_total             1904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00069_si_002.cif
_cod_data_source_block           1703hox
_cod_original_cell_volume        1007.40(8)
_cod_database_code               4035167
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C28 h26 o8 n4'
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_reflns_odcompleteness_theta     72.65
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C14(H14), C15(H15), C11(H11), C5(H5), C2(H2), C3(H3), C4(H4)
;
_shelx_res_checksum              62992
_shelx_hkl_checksum              49609
_olex2_submission_special_instructions 'No special instructions were received'