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_4034640
_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 O'
_chemical_formula_sum            'C13 H13 Cl3 N2 O'
_chemical_formula_weight         319.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
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Olex2 1.2
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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)
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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)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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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;
Palatinus et al., 2012)
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_diffrn_ambient_temperature      100(2)
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  1 omega  -90.00  -48.00   1.0000   21.2100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000  -60.0000 42

  2 omega  -51.00   -5.00   1.0000   21.2100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -19.0000  120.0000 46

  3 omega  -90.00    0.00   1.0000   21.2100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -38.0000  -90.0000 90

  4 omega   35.00   89.00   1.0000   21.2100
omega____ theta____ kappa____ phi______ frames
    -       23.3616  178.0000 -150.0000 54
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_unetI/netI     0.0397
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_diffrn_reflns_Laue_measured_fraction_max 0.893
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_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_theta_max         30.816
_diffrn_reflns_theta_min         2.560
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97348
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_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.
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_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.390
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         3993
_refine_ls_number_restraints     0
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0218P)^2^+0.6366P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00812_si_002.cif
_cod_data_source_block           9827-11453_ca217_ii
_cod_original_cell_volume        1427.63(7)
_cod_database_code               4034640
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'Cl3 C13 N2 O'
_shelx_estimated_absorpt_t_max   0.777
_shelx_estimated_absorpt_t_min   0.734
_reflns_odcompleteness_completeness 99.87
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_reflns_odcompleteness_theta     28.51
_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:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C9(H9)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
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_olex2_submission_special_instructions 'No special instructions were received'