Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles
Aksenov, Alexander V.; Khamraev, Vladislav; Aksenov, Nicolai A.; Kirilov, Nikita K.; Domenyuk, Dmitriy A.; Zelensky, Vladimir A.; Rubin, Michael; RSC Advances 9 (2019) 6636–; doi:10.1039/C9RA00976K

data_7232443
_publ_section_title
;
 Electrophilic activation of nitroalkanes in efficient synthesis of
 1,3,4-oxadiazoles
;
_journal_issue                   12
_journal_name_full               'RSC Advances'
_journal_page_first              6636
_journal_paper_doi               10.1039/C9RA00976K
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H10 N2 O'
_chemical_formula_sum            'C14 H10 N2 O'
_chemical_formula_weight         222.24
_chemical_name_systematic        2,5-diphenyl-1,3,4-oxadiazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-28 deposited with the CCDC.    2019-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7321(12)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   12.71311(16)
_cell_length_b                   23.6491(3)
_cell_length_c                   22.6770(3)
_cell_measurement_reflns_used    66441
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      75.7070
_cell_measurement_theta_min      3.6740
_cell_volume                     6675.49(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -72.00  35.00   1.00    2.00    --  -41.72  27.00-168.00  107
  2  \w   -119.00 -11.00   1.00    2.00    --  -41.72 -27.00  29.00  108
  3  \w    -35.00  72.00   1.00    2.00    --   41.72 -27.00  29.00  107
  4  \w     11.00 119.00   1.00    2.00    --   41.72  27.00-168.00  108
  5  \w     35.00 143.00   1.00    8.00    --  112.00 -27.00  29.00  108
  6  \w     81.00 178.00   1.00    8.00    --  112.00  27.00-168.00   97
  7  \w     23.00  98.00   1.00    2.00    --   41.72-125.00 -90.00   75
  8  \w     23.00  98.00   1.00    2.00    --   41.72-125.00 150.00   75
  9  \w     23.00  98.00   1.00    2.00    --   41.72-125.00  90.00   75
 10  \w     36.00 116.00   1.00    8.00    --  112.00-111.00-150.00   80
 11  \w     39.00 138.00   1.00    8.00    --  112.00 -45.00  90.00   99
 12  \w     36.00 116.00   1.00    8.00    --  112.00-111.00 -90.00   80
 13  \w    100.00 178.00   1.00    8.00    --  112.00 111.00-180.00   78
 14  \w     83.00 178.00   1.00    8.00    --  112.00  61.00  90.00   95
 15  \w     57.00 151.00   1.00    8.00    --  112.00 178.00  30.00   94
 16  \w     40.00 141.00   1.00    8.00    --  112.00 -61.00-120.00  101
 17  \w     86.00 178.00   1.00    8.00    --  112.00  45.00-150.00   92
 18  \w     29.00  93.00   1.00    8.00    --  112.00 -94.00-120.00   64
 19  \w     30.00 109.00   1.00    8.00    --  112.00 -94.00  90.00   79
 20  \w     56.00 107.00   1.00    8.00    --  112.00-111.00  30.00   51
 21  \w      8.00  33.00   1.00    2.00    --  -41.60  38.00  90.00   25
 22  \w     64.00  94.00   1.00    8.00    --  112.00 -94.00  60.00   30
 23  \w     54.00  85.00   1.00    8.00    --  112.00 -30.00 -90.00   31
 24  \w   -118.00  -9.00   1.00    2.00    --  -41.60 -77.00  60.00  109
 25  \w   -118.00  -9.00   1.00    2.00    --  -41.60 -77.00 120.00  109
 26  \w   -114.00 -13.00   1.00    2.00    --  -41.60 -57.00 -60.00  101
 27  \w   -118.00  -9.00   1.00    2.00    --  -41.60 -77.00-150.00  109
 28  \w   -118.00  -9.00   1.00    2.00    --  -41.60 -77.00 -60.00  109
 29  \w      1.00  82.00   1.00    2.00    --   41.60 -99.00 -30.00   81
 30  \w     86.00 178.00   1.00    8.00    --  112.00  45.00  30.00   92
 31  \w     83.00 178.00   1.00    8.00    --  112.00  61.00 120.00   95
 32  \w     83.00 178.00   1.00    8.00    --  112.00  61.00 -30.00   95
 33  \w     84.00 178.00   1.00    8.00    --  112.00  30.00 -60.00   94
 34  \w     41.00  66.00   1.00    2.00    --   41.60  27.00-168.00   25
 35  \w    -39.00 -13.00   1.00    2.00    --  -41.60 -57.00   0.00   26
 36  \w     33.00  59.00   1.00    2.00    --   62.00  75.00  -5.70   26
 37  \w     38.00  63.00   1.00    2.00    --   70.00  76.00 -76.57   25
 38  \w     40.00  66.00   1.00    2.00    --   70.00  77.00 -58.93   26
 39  \w     41.00  69.00   1.00    2.00    --   74.00  77.00  -6.53   28
 40  \w     44.00  70.00   1.00    2.00    --   74.00  76.00  39.61   26
 41  \w     59.00  85.00   1.00    2.00    --   74.00  77.00-121.44   26
 42  \w     44.00  73.00   1.00    2.00    --   74.00  77.00 -52.70   29
 43  \w     45.00  73.00   1.00    8.00    --   78.00  77.00 -67.47   28
 44  \w     79.00 133.00   1.00    8.00    --  112.00  77.00 -60.00   54
 45  \w    130.00 178.00   1.00    8.00    --  112.00  77.00-150.00   48
 46  \w     83.00 135.00   1.00    8.00    --  112.00  61.00 -90.00   52
 47  \w     84.00 154.00   1.00    8.00    --  112.00  61.00-120.00   70
 48  \w     83.00 110.00   1.00    8.00    --  112.00  61.00   0.00   27
 49  \w     80.00 106.00   1.00    8.00    --  112.00  77.00-150.00   26
 50  \w     79.00 104.00   1.00    8.00    --  112.00  77.00-120.00   25
 51  \w     79.00 104.00   1.00    8.00    --  112.00  77.00 -30.00   25
 52  \w     79.00 105.00   1.00    8.00    --  112.00  77.00   0.00   26
 53  \w    122.00 148.00   1.00    8.00    --  112.00  77.00   0.00   26
 54  \w     87.00 113.00   1.00    8.00    --  112.00  45.00   0.00   26
 55  \w     88.00 115.00   1.00    8.00    --  112.00  45.00 -90.00   27
 56  \w     90.00 116.00   1.00    8.00    --  112.00  45.00 -60.00   26
 57  \w     79.00 105.00   1.00    8.00    --  112.00  77.00 -90.00   26
 58  \w    127.00 153.00   1.00    8.00    --  112.00  61.00   0.00   26
 59  \w     83.00 111.00   1.00    8.00    --  112.00  61.00 -60.00   28
 60  \w      4.00  32.00   1.00    2.00    --   41.60  90.00 125.62   28
 61  \w     20.00  46.00   1.00    2.00    --   54.00  81.00 -45.80   26
 62  \w     21.00  47.00   1.00    2.00    --   54.00  79.00-140.52   26
 63  \w     20.00  46.00   1.00    2.00    --   54.00  81.00 117.76   26
 64  \w     21.00  47.00   1.00    2.00    --   54.00  79.00  66.19   26
 65  \w     20.00  46.00   1.00    2.00    --   54.00  81.00 -97.61   26
 66  \w     21.00  47.00   1.00    2.00    --   54.00  79.00  21.40   26
 67  \w     20.00  46.00   1.00    2.00    --   54.00  81.00  88.96   26
 68  \w     20.00  46.00   1.00    2.00    --   54.00  81.00-179.44   26
 69  \w     37.00 146.00   1.00    2.00    --   70.00  77.00 119.10  109
 70  \w     37.00 146.00   1.00    2.00    --   70.00  77.00  14.68  109
 71  \w     41.00 150.00   1.00    2.00    --   74.00  77.00-121.44  109
 72  \w     41.00 150.00   1.00    2.00    --   74.00  77.00 170.03  109
 73  \w     41.00 150.00   1.00    2.00    --   74.00  77.00 155.71  109
 74  \w     42.00 133.00   1.00    2.00    --   74.00  76.00  64.53   91
 75  \w     42.00 150.00   1.00    2.00    --   74.00  76.00  91.83  108
 76  \w     42.00 150.00   1.00    2.00    --   74.00  76.00  39.61  108
 77  \w     41.00 150.00   1.00    2.00    --   74.00  77.00 -52.70  109
 78  \w     42.00 149.00   1.00    2.00    --   74.00  75.00  57.71  107
 79  \w     41.00 150.00   1.00    2.00    --   74.00  77.00-164.56  109
 80  \w     42.00 150.00   1.00    2.00    --   74.00  76.00-139.14  108
 81  \w     65.00  90.00   1.00    8.00    --  112.00 -27.00  28.00   25
 82  \w     41.00  66.00   1.00    2.00    --   41.60  27.00-168.00   25
 83  \w     41.00  66.00   1.00    2.00    --   41.60  27.00-168.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0889333000
_diffrn_orient_matrix_UB_12      -0.0077884000
_diffrn_orient_matrix_UB_13      -0.0364258000
_diffrn_orient_matrix_UB_21      0.0841736000
_diffrn_orient_matrix_UB_22      0.0211317000
_diffrn_orient_matrix_UB_23      0.0542361000
_diffrn_orient_matrix_UB_31      0.0179436000
_diffrn_orient_matrix_UB_32      -0.0611119000
_diffrn_orient_matrix_UB_33      0.0234091000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            105927
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.258
_diffrn_reflns_theta_min         3.738
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             2784
_exptl_crystal_preparation       'Prepared by cyclisation of hydrazide in PPA'
_exptl_crystal_recrystallization_method
'Crystallized by slow evaporation of saturated solution'
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.458
_exptl_crystal_size_min          0.249
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 6098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     813
_refine_ls_number_reflns         13719
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0768
_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^)+(0.1107P)^2^+11.7823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2005
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                13482
_reflns_number_total             13719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra00976k2.cif
_cod_data_source_block           anna_16002018_vlad211_3
_cod_original_cell_volume        6675.51(15)
_cod_database_code               7232443
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H10N2O
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.720
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C25) = Uanis(C32)
Uanis(C26) = Uanis(C23)
Uanis(C23) = Uanis(C26)
Uanis(C7) = Uanis(C15)
Uanis(C16) = Uanis(C9)
Uanis(C10) = Uanis(C2)
Uanis(C1) = Uanis(C8)
3. Others
 Sof(N4)=Sof(N3)=Sof(C1)=Sof(C16)=1-FVAR(1)
 Sof(N1)=Sof(N2)=Sof(C8)=Sof(C9)=FVAR(1)
 Sof(C17)=Sof(N6)=Sof(N5)=Sof(C32)=1-FVAR(2)
 Sof(N7)=Sof(N8)=Sof(C24)=Sof(C25)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C53(H53), C51(H51), C52(H52), C50(H50), C49(H49), C74(H74), C73(H73),
 C72(H72), C71(H71), C70(H70), C56(H56), C57(H57), C58(H58), C59(H59), C60(H60),
  C82(H82), C81(H81), C80(H80), C79(H79), C78(H78), C42(H42), C43(H43),
 C44(H44), C45(H45), C46(H46), C38(H38), C39(H39), C37(H37), C36(H36), C35(H35),
  C85(H85), C86(H86), C87(H87), C88(H88), C89(H89), C67(H67), C66(H66),
 C65(H65), C64(H64), C63(H63), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
  C22(H22), C21(H21), C20(H20), C19(H19), C18(H18), C6(H6), C5(H5), C4(H4),
 C3(H3), C2(H2), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
4.b Fitted hexagon refined as free rotating group:
 C48(C53,C51,C52,C50,C49), C69(C74,C73,C72,C71,C70), C55(C56,C57,C58,C59,C60),
 C76(C82,C81,C80,C79,C78), C41(C42,C43,C44,C45,C46), C34(C38,C39,C37,C36,C35),
 C84(C85,C86,C87,C88,C89), C62(C67,C66,C65,C64,C63), C10(C11,C12,C13,C14,C15),
 C23(C22,C21,C20,C19,C18), C7(C6,C5,C4,C3,C2), C26(C27,C28,C29,C30,C31)
;
_shelx_res_checksum              67040
_olex2_exptl_crystal_mounting_method
'Mounted by acrylic glue on the glass stick'
_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 2.099
_oxdiff_exptl_absorpt_empirical_full_min 0.664