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_4034642
_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         'C18 H17 F N2 O'
_chemical_formula_sum            'C18 H17 F N2 O'
_chemical_formula_weight         296.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-25
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_cell_angle_alpha                90.884(4)
_cell_angle_beta                 103.956(4)
_cell_angle_gamma                95.264(4)
_cell_formula_units_Z            2
_cell_length_a                   7.5047(3)
_cell_length_b                   9.2211(4)
_cell_length_c                   11.4499(6)
_cell_measurement_reflns_used    4475
_cell_measurement_temperature    114(2)
_cell_measurement_theta_max      72.1620
_cell_measurement_theta_min      3.9530
_cell_volume                     765.14(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      114(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_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    -13.00  37.00   0.50    0.53    --   38.95 -79.00 139.00  100
  2  \w     82.00 110.00   0.50    2.12    --  104.29  79.00 -96.00   56
  3  \w    118.00 152.00   0.50    2.12    --  104.29  79.00 -96.00   68
  4  \w     60.00 129.00   0.50    2.12    --  104.29 -79.00 139.00  138
  5  \w    -48.00 -16.00   0.50    0.53    --  -38.95 -65.00-120.00   64
  6  \w    -51.00 -22.00   0.50    0.53    --  -38.95  32.00-120.00   58
  7  \w    -35.00   6.00   0.50    0.53    --  -38.95 104.00   0.00   82
  8  \w   -100.00 -57.00   0.50    0.53    --  -38.95 -65.00-120.00   86
  9  \w    -77.00 -40.00   0.50    0.53    --  -38.95 104.00   0.00   74
 10  \w    -41.00  27.00   0.50    0.53    --  -38.95  79.00 -96.00  136
 11  \w     -2.00  24.00   0.50    0.53    --  -38.95  32.00-120.00   52
 12  \w   -101.00 -23.00   0.50    0.53    --  -38.95 -43.00  30.00  156
 13  \w    -58.00 -21.00   0.50    0.53    --  -38.95  54.00  30.00   74
 14  \w     41.00  97.00   0.50    0.53    --   38.95-138.00 -90.00  112
 15  \w     11.00  38.00   0.50    0.53    --   38.95-138.00 -90.00   54
 16  \w     67.00 105.00   0.50    0.53    --   38.95  43.00   0.00   76
 17  \w    -31.00   5.00   0.50    0.53    --   38.95 -89.00 120.00   72
 18  \w     27.00  52.00   0.50    0.53    --   38.95  43.00   0.00   50
 19  \w      1.00  51.00   0.50    0.53    --   38.95 -65.00  60.00  100
 20  \w     83.00 108.00   0.50    0.53    --   38.95  32.00 -60.00   50
 21  \w     14.00  39.00   0.50    0.53    --   38.95 -32.00 -60.00   50
 22  \w    -26.00  11.00   0.50    0.53    --   38.95 -43.00 120.00   74
 23  \w     13.00  54.00   0.50    0.53    --   38.95 -89.00 120.00   82
 24  \w     49.00  79.00   0.50    0.53    --   38.95  32.00 -60.00   60
 25  \w    -22.00   8.00   0.50    0.53    --   38.95 -32.00 -60.00   60
 26  \w     28.00  58.00   0.50    0.53    --   38.95 -54.00 120.00   60
 27  \w     11.00  37.00   0.50    0.53    --   38.95 -54.00   0.00   52
 28  \w     40.00 117.00   0.50    2.12    --  104.29-133.00 -30.00  154
 29  \w     82.00 157.00   0.50    2.12    --  104.29  61.00 -60.00  150
 30  \w     47.00 103.00   0.50    2.12    --  104.29 -53.00-120.00  112
 31  \w     67.00 110.00   0.50    2.12    --  104.29-111.00   0.00   86
 32  \w     45.00 124.00   0.50    2.12    --  104.29 -53.00 120.00  158
 33  \w     91.00 155.00   0.50    2.12    --  104.29  30.00-150.00  128
 34  \w     93.00 119.00   0.50    2.12    --  104.29  15.00   0.00   52
 35  \w    115.00 149.00   0.50    2.12    --  104.29  37.00  90.00   68
 36  \w     87.00 117.00   0.50    2.12    --  104.29 -30.00  30.00   60
 37  \w     66.00 105.00   0.50    2.12    --  104.29 -37.00 120.00   78
 38  \w     95.00 154.00   0.50    2.12    --  104.29  37.00 -30.00  118
 39  \w     82.00 107.00   0.50    2.12    --  104.29  93.00   0.00   50
 40  \w     35.00  77.00   0.50    2.12    --  104.29-111.00  90.00   84
 41  \w     35.00  68.00   0.50    2.12    --  104.29 -30.00  30.00   66
 42  \w     69.00 121.00   0.50    2.12    --  104.29-133.00 150.00  104
 43  \w     76.00 105.00   0.50    2.12    --  104.29 -86.00   0.00   58
 44  \w     38.00  64.00   0.50    2.12    --  104.29 -37.00 120.00   52
 45  \w     41.00 103.00   0.50    2.12    --  104.29 -30.00 -90.00  124
 46  \w     55.00  91.00   0.50    2.12    --  104.29-111.00 -30.00   72
 47  \w     39.00  73.00   0.50    2.12    --  104.29 -86.00   0.00   68
 48  \w     80.00 111.00   0.50    2.12    --  104.29-111.00-180.00   62
 49  \w     37.00  69.00   0.50    2.12    --  104.29-111.00-180.00   64
 50  \w     35.00  86.00   0.50    2.12    --  104.29-111.00 150.00  102
 51  \w    132.00 157.00   0.50    2.12    --  104.29  93.00   0.00   50
 52  \w     83.00 109.00   0.50    2.12    --  104.29-111.00 -90.00   52
 53  \w     85.00 121.00   0.50    2.12    --  104.29  53.00 -90.00   72
 54  \w    129.00 155.00   0.50    2.12    --  104.29  15.00   0.00   52
 55  \w    118.00 144.00   0.50    2.12    --  104.29  45.00   0.00   52
 56  \w     78.00 117.00   0.50    2.12    --  104.29 133.00-180.00   78
 57  \w     80.00 157.00   0.50    2.12    --  104.29 111.00-150.00  154
 58  \w    108.00 152.00   0.50    2.12    --  104.29 133.00 150.00   88
 59  \w     57.00  83.00   0.50    0.53    --   38.95  54.00 150.00   52
 60  \w    -39.00 -14.00   0.50    0.53    --    4.00 112.00 -98.86   50
 61  \w    -16.00  10.00   0.50    0.53    --   20.00 106.00 -27.58   52
 62  \w     -8.00  17.00   0.50    0.53    --   28.00 100.00-157.66   50
 63  \w     -1.00  24.00   0.50    0.53    --   32.00  92.00  60.01   50
 64  \w     -1.00  24.00   0.50    0.53    --   32.00  94.00 166.70   50
 65  \w      6.00  31.00   0.50    0.53    --   36.00  86.00-100.43   50
 66  \w      6.00  31.00   0.50    0.53    --   36.00  87.00 100.27   50
 67  \w      5.00  30.00   0.50    0.53    --   36.00  88.00 -24.17   50
 68  \w     11.00  36.00   0.50    0.53    --   40.00  84.00  34.47   50
 69  \w     16.00  41.00   0.50    0.53    --   44.00  82.00  56.70   50
 70  \w     16.00  41.00   0.50    0.53    --   44.00  80.00  89.97   50
 71  \w     16.00  41.00   0.50    0.53    --   44.00  81.00-171.93   50
 72  \w     16.00  41.00   0.50    0.53    --   44.00  82.00 133.16   50
 73  \w     17.00  42.00   0.50    0.53    --   44.00  79.00 -19.76   50
 74  \w     16.00  41.00   0.50    0.53    --   44.00  82.00 -83.99   50
 75  \w     16.00  41.00   0.50    0.53    --   44.00  82.00-129.09   50
 76  \w     28.00  67.00   0.50    0.53    --   48.00  71.00  44.87   78
 77  \w     26.00  52.00   0.50    0.53    --   52.00  77.00-161.73   52
 78  \w     26.00  51.00   0.50    0.53    --   52.00  76.00 161.90   50
 79  \w     85.00 111.00   0.50    0.53    --   56.00  77.00  44.15   52
 80  \w     32.00  79.00   0.50    0.53    --   56.00  77.00  44.15   94
 81  \w     32.00  63.00   0.50    0.53    --   56.00  69.00 -39.42   62
 82  \w     35.00 110.00   0.50    0.53    --   60.00  70.00 139.57  150
 83  \w    100.00 126.00   0.50    0.53    --   60.00  77.00  94.94   52
 84  \w     33.00  83.00   0.50    0.53    --   60.00  77.00  -6.97  100
 85  \w     70.00  96.00   0.50    0.53    --   60.00  64.00-166.07   52
 86  \w     39.00  65.00   0.50    0.53    --   60.00  64.00-166.07   52
 87  \w     35.00  75.00   0.50    0.53    --   60.00  76.00 -90.87   80
 88  \w     37.00  63.00   0.50    0.53    --   60.00  69.00-140.27   52
 89  \w     35.00  75.00   0.50    0.53    --   60.00  77.00  94.94   80
 90  \w     42.00  67.00   0.50    0.53    --   64.00  59.00-103.48   50
 91  \w     80.00 123.00   0.50    0.53    --   64.00  60.00-142.80   86
 92  \w     43.00  69.00   0.50    0.53    --   64.00  60.00-142.80   52
 93  \w     41.00  80.00   0.50    0.53    --   64.00  77.00 -44.19   78
 94  \w     55.00 111.00   0.50    2.12    --   80.00  73.00  88.75  112
 95  \w     58.00  84.00   0.50    2.12    --   84.00  76.00-126.20   52
 96  \w     68.00 106.00   0.50    2.12    --   92.00  68.00-171.76   76
 97  \w     80.00  96.00   0.50    2.12    --  104.29  77.00 -60.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0286982000
_diffrn_orient_matrix_UB_12      -0.0832870000
_diffrn_orient_matrix_UB_13      -0.1106522000
_diffrn_orient_matrix_UB_21      -0.2095822000
_diffrn_orient_matrix_UB_22      -0.0419815000
_diffrn_orient_matrix_UB_23      -0.0422830000
_diffrn_orient_matrix_UB_31      -0.0207517000
_diffrn_orient_matrix_UB_32      0.1396163000
_diffrn_orient_matrix_UB_33      -0.0722394000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9305
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.520
_diffrn_reflns_theta_min         3.981
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.286
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0531P)^2^+0.2111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2488
_reflns_number_total             2990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00812_si_005.cif
_cod_data_source_block           9827-10660_ca263
_cod_database_code               4034642
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C17 F N2 O'
_diffrn_oxdiff_ac3_digest_frames
;
018a3a8329d960e9738ef92793e58bd39c000270d6d
;
_diffrn_oxdiff_ac3_digest_hkl
;
01d9f97a38fe4ca6efd7efcae1c5d4f7fffafa
;
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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:
 C7(H7), C6(H6), C12(H12), C10(H10), C9(H9), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C3(H3A,H3B,H3C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              82750
_shelx_hkl_checksum              26936
_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 2.048
_oxdiff_exptl_absorpt_empirical_full_min 0.766