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_7232445
_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_formula_moiety         'C8 H7 N3 O'
_chemical_formula_sum            'C8 H7 N3 O'
_chemical_formula_weight         161.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 102.454(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.38130(10)
_cell_length_b                   19.4244(4)
_cell_length_c                   7.4718(2)
_cell_measurement_reflns_used    11268
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0650
_cell_measurement_theta_min      4.4790
_cell_volume                     762.64(3)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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 -59.00   0.50    1.00    --  -41.35-147.00  25.00  110
  2  \w    -96.00  -2.00   0.50    1.00    --  -41.35 125.00 -90.00  188
  3  \w   -108.00 -13.00   0.50    1.00    --  -41.35 147.00  75.00  190
  4  \w     23.00  97.00   0.50    1.00    --   41.35-125.00-168.00  148
  5  \w     35.00 112.00   0.50    1.00    --   41.35-147.00  25.00  154
  6  \w     39.00 121.00   0.50    3.07    --  112.00-125.00-168.00  164
  7  \w     81.00 174.00   0.50    3.07    --  112.00 147.00  75.00  186
  8  \w     39.00 133.00   0.50    3.07    --  112.00-147.00  25.00  188
  9  \w     94.00 178.00   0.50    3.07    --  112.00 125.00 -90.00  168
 10  \w   -116.00 -17.00   0.50    1.00    --  -41.35 -38.00-180.00  198
 11  \w   -113.00 -13.00   0.50    1.00    --  -41.35 -57.00  90.00  200
 12  \w     23.00  97.00   0.50    1.00    --   41.35-125.00  30.00  148
 13  \w     17.00 116.00   0.50    1.00    --   41.35  38.00  90.00  198
 14  \w    100.00 178.00   0.50    3.07    --  112.00 111.00 120.00  156
 15  \w     57.00 151.00   0.50    3.07    --  112.00 178.00  30.00  188
 16  \w     39.00 138.00   0.50    3.07    --  112.00 -45.00 -30.00  198
 17  \w     36.00 140.00   0.50    3.07    --  112.00 -30.00  60.00  208
 18  \w     40.00 141.00   0.50    3.07    --  112.00 -61.00 150.00  202
 19  \w     57.00 151.00   0.50    3.07    --  112.00 178.00 -30.00  188
 20  \w     36.00 116.00   0.50    3.07    --  112.00-111.00 120.00  160
 21  \w     83.00 178.00   0.50    3.07    --  112.00  61.00-180.00  190
 22  \w     57.00 151.00   0.50    3.07    --  112.00 178.00 150.00  188
 23  \w     86.00 178.00   0.50    3.07    --  112.00  45.00  60.00  184
 24  \w     36.00 116.00   0.50    3.07    --  112.00-111.00  30.00  160
 25  \w     29.00 109.00   0.50    3.07    --  112.00 -94.00   0.00  160
 26  \w     57.00 151.00   0.50    3.07    --  112.00 178.00 -60.00  188
 27  \w     83.00 178.00   0.50    3.07    --  112.00  61.00   0.00  190
 28  \w    100.00 178.00   0.50    3.07    --  112.00 111.00-120.00  156
 29  \w    100.00 178.00   0.50    3.07    --  112.00 111.00  60.00  156
 30  \w     29.00 109.00   0.50    3.07    --  112.00 -94.00  30.00  160
 31  \w   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00 150.00  216
 32  \w   -113.00 -13.00   0.50    1.00    --  -41.35 -57.00 -90.00  200
 33  \w   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00 120.00  216
 34  \w   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00 -90.00  216
 35  \w   -113.00 -13.00   0.50    1.00    --  -41.35 -57.00 -60.00  200
 36  \w   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00  30.00  216
 37  \w   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00-120.00  216
 38  \w      1.00  82.00   0.50    1.00    --   41.35 -99.00-120.00  162
 39  \w      1.00  82.00   0.50    1.00    --   41.35 -99.00  90.00  162
 40  \w     83.00 178.00   0.50    3.07    --  112.00  61.00-150.00  190
 41  \w     83.00 178.00   0.50    3.07    --  112.00  61.00  90.00  190
 42  \w     86.00 178.00   0.50    3.07    --  112.00  45.00 -30.00  184
 43  \w     83.00 178.00   0.50    3.07    --  112.00  61.00 120.00  190
 44  \w     83.00 178.00   0.50    3.07    --  112.00  61.00 150.00  190
 45  \w     59.00 178.00   0.50    3.07    --  112.00  15.00 -60.00  238
 46  \w     83.00 178.00   0.50    3.07    --  112.00  61.00 -90.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0995809000
_diffrn_orient_matrix_UB_12      0.0506357000
_diffrn_orient_matrix_UB_13      0.1270612000
_diffrn_orient_matrix_UB_21      0.1068177000
_diffrn_orient_matrix_UB_22      0.0607780000
_diffrn_orient_matrix_UB_23      -0.0924096000
_diffrn_orient_matrix_UB_31      -0.2541759000
_diffrn_orient_matrix_UB_32      0.0057396000
_diffrn_orient_matrix_UB_33      -0.1410792000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18612
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.173
_diffrn_reflns_theta_min         4.553
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.404
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.531
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0501P)^2^+0.0413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3080
_reflns_number_total             3181
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra00976k2.cif
_cod_data_source_block           anna_vlad229_5
_cod_database_code               7232445
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.673
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6(2)
 0.4(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C12(H12), C6(H6), C15(H15), C5(H5), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              78078
_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 2.531
_oxdiff_exptl_absorpt_empirical_full_min 0.610