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_7232444
_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         'C9 H6 Cl2 N2 O'
_chemical_formula_sum            'C9 H6 Cl2 N2 O'
_chemical_formula_weight         229.06
_chemical_name_systematic
2-(2,4-dichlorophenyl)-5-methyl-1,3,4-oxadiazole
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.366(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5227(2)
_cell_length_b                   3.96920(10)
_cell_length_c                   20.5396(4)
_cell_measurement_reflns_used    8087
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.6530
_cell_measurement_theta_min      4.2170
_cell_volume                     937.78(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_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.997
_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    -66.00  33.00   1.00    1.00    --  -41.35  38.00 -30.00   99
  2  \w    -66.00  33.00   1.00    1.00    --  -41.35  38.00-120.00   99
  3  \w     23.00  97.00   1.00    1.00    --   41.35-125.00-180.00   74
  4  \w     36.00 140.00   1.00    4.00    --  112.00 -30.00-120.00  104
  5  \w     84.00 178.00   1.00    4.00    --  112.00  30.00-150.00   94
  6  \w     36.00 116.00   1.00    4.00    --  112.00-111.00 150.00   80
  7  \w     86.00 178.00   1.00    4.00    --  112.00  45.00  30.00   92
  8  \w     57.00 151.00   1.00    4.00    --  112.00 178.00   0.00   94
  9  \w     57.00 151.00   1.00    4.00    --  112.00 178.00 -30.00   94
 10  \w     40.00 141.00   1.00    4.00    --  112.00 -61.00 -90.00  101
 11  \w     59.00 178.00   1.00    4.00    --  112.00  15.00 -30.00  119
 12  \w    100.00 178.00   1.00    4.00    --  112.00 111.00-150.00   78
 13  \w   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00  90.00  108
 14  \w   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00 -60.00  100
 15  \w   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00-150.00  108
 16  \w     83.00 178.00   1.00    4.00    --  112.00  61.00-120.00   95
 17  \w     79.00 178.00   1.00    4.00    --  112.00  77.00 -30.00   99
 18  \w     86.00 178.00   1.00    4.00    --  112.00  45.00 150.00   92
 19  \w     83.00 174.00   1.00    4.00    --  112.00  61.00  60.00   91
 20  \w     84.00 178.00   1.00    4.00    --  112.00  30.00 120.00   94
;
_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      -0.0076786000
_diffrn_orient_matrix_UB_12      -0.0576720000
_diffrn_orient_matrix_UB_13      -0.0742891000
_diffrn_orient_matrix_UB_21      0.1333482000
_diffrn_orient_matrix_UB_22      -0.0294562000
_diffrn_orient_matrix_UB_23      0.0009055000
_diffrn_orient_matrix_UB_31      -0.0091314000
_diffrn_orient_matrix_UB_32      -0.3828914000
_diffrn_orient_matrix_UB_33      0.0111201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9403
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.941
_diffrn_reflns_theta_min         4.295
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.947
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.784
_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    1.622
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_preparation       'Was prepared from nitrocompound and hydrazide'
_exptl_crystal_recrystallization_method
'Crystallized by evaporation of saturated solution'
_exptl_crystal_size_max          0.658
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.182
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0115(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0540P)^2^+0.4398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1917
_reflns_number_total             1940
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra00976k2.cif
_cod_data_source_block           anna_vlad240_3
_cod_database_code               7232444
_shelx_shelxl_version_number     2018/3
_publ_section_exptl
;
Any special experimental details
;
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.411
_shelx_estimated_absorpt_t_min   0.111
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C8(H8)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              94017
_olex2_date_sample_data_collection 2018-04-06
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 3.893
_oxdiff_exptl_absorpt_empirical_full_min 0.579