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_4034639
_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         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_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     dual
_audit_creation_date             2018-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.053(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8072(7)
_cell_length_b                   6.0525(4)
_cell_length_c                   16.8346(9)
_cell_measurement_reflns_used    2935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.1690
_cell_measurement_theta_min      6.1980
_cell_volume                     1304.72(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.921
_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   -114.00 -25.00   1.00    1.00    --  -40.38 -57.00 -60.00   89
  2  \w   -119.00 -13.00   1.00    1.00    --  -40.38 -77.00-150.00  106
  3  \w     33.00 108.00   1.00    1.00    --  113.00 -95.00  60.00   75
  4  \w     92.00 131.00   1.00    1.00    --  113.00 -45.00 150.00   39
  5  \w     42.00  74.00   1.00    1.00    --  113.00 -45.00 150.00   32
  6  \w    117.00 175.00   1.00    1.00    --  113.00 112.00   0.00   58
  7  \w    144.00 170.00   1.00    1.00    --  113.00 112.00 -90.00   26
  8  \w    112.00 147.00   1.00    1.00    --  113.00  77.00-120.00   35
  9  \w    101.00 165.00   1.00    1.00    --  113.00 112.00-120.00   64
 10  \w     58.00 107.00   1.00    1.00    --   40.38 178.00-150.00   49
 11  \w     57.00 134.00   1.00    1.00    --  113.00 178.00  60.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0622609000
_diffrn_orient_matrix_UB_12      -0.2130258000
_diffrn_orient_matrix_UB_13      0.0166679000
_diffrn_orient_matrix_UB_21      -0.0745202000
_diffrn_orient_matrix_UB_22      -0.0582762000
_diffrn_orient_matrix_UB_23      0.0676154000
_diffrn_orient_matrix_UB_31      -0.0708525000
_diffrn_orient_matrix_UB_32      -0.1271105000
_diffrn_orient_matrix_UB_33      -0.0593540000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4425
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.141
_diffrn_reflns_theta_min         3.452
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0679P)^2^+0.3686P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2261
_reflns_number_total             2516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00812_si_004.cif
_cod_data_source_block           9827-11378_ca203ii
_cod_database_code               4034639
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'O N2 C16'
_shelx_estimated_absorpt_t_max   0.743
_shelx_estimated_absorpt_t_min   0.703
_reflns_odcompleteness_completeness 94.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C16(H16), C10(H10), C12(H12), C7(H7), C8(H8), C15(H15), C9(H9),
 C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              40908
_shelx_hkl_checksum              69009
_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 3.957
_oxdiff_exptl_absorpt_empirical_full_min 0.331