Synthesis of 1,2,4-Oxadiazoles by Tandem Reaction of Nitroalkenes with Arenes and Nitriles in the Superacid TfOH.
Golushko, Andrei A.; Khoroshilova, Olesya V.; Vasilyev, Aleksander V.; The Journal of organic chemistry 84 (2019) 7495–7500; doi:10.1021/acs.joc.9b00812

data_4034641
_publ_section_title
;
 Synthesis of 1,2,4-Oxadiazoles by Tandem Reaction of Nitroalkenes with
 Arenes and Nitriles in the Superacid TfOH.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7495
_journal_page_last               7500
_journal_paper_doi               10.1021/acs.joc.9b00812
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C13 H13 Cl3 N2 O3'
_chemical_formula_sum            'C13 H13 Cl3 N2 O3'
_chemical_formula_weight         351.60
_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_computing_cell_refinement
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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)
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_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)
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_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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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_diffrn_ambient_temperature      100.01(10)
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  1 omega  -69.00   47.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -90.00   -4.00   1.0000    2.5000
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  3 omega    5.00   36.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  4 omega   33.00  101.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  5 omega  -10.00   63.00   1.0000    2.5000
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  6 omega   23.00   69.00   1.0000    2.5000
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  8 omega  -93.00   -4.00   1.0000    2.5000
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omega____ theta____ kappa____ phi______ frames
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 12 omega  -82.00  -51.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -25.5873    0.0000  -60.0000 31
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_diffrn_orient_matrix_UB_33      -0.0581116000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_l_min       -14
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_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.607
_diffrn_source                   'Enhance (Mo) X-ray Source'
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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.
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_exptl_crystal_colour            'clear colourless'
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0188P)^2^+0.4481P] where P=(Fo^2^+2Fc^2^)/3'
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_cod_original_cell_volume        734.58(6)
_cod_database_code               4034641
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C13 Cl3 N2 O3'
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_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:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              16266
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_olex2_submission_special_instructions 'No special instructions were received'