Electrochemically promoted annulation of aldehydes and carbazates: access to 2-alkoxy/aryloxy-5-substituted 1,3,4-oxadiazole and 1,3,4-oxadiazol-2(3H)-one derivatives
Li, Hongjun; Tang, Dong; Iqbal, Zafar; Wan, Yaya; Jiang, Rui; Yang, Zhixiang; Yang, Jinhui; New Journal of Chemistry 46 (2022) 20347–20353; doi:10.1039/D2NJ04113H

data_7061977
_publ_section_title
;
 Electrochemically promoted annulation of aldehydes and carbazates: access
 to 2-alkoxy/aryloxy-5-substituted 1,3,4-oxadiazole and
 1,3,4-oxadiazol-2(3H)-one derivatives
;
_journal_issue                   42
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20347
_journal_page_last               20353
_journal_paper_doi               10.1039/D2NJ04113H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C14 H18 N2 O2'
_chemical_formula_sum            'C14 H18 N2 O2'
_chemical_formula_weight         246.30
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-10
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-07-22 deposited with the CCDC.	2022-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.909(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1933(4)
_cell_length_b                   17.2296(12)
_cell_length_c                   11.4006(6)
_cell_measurement_reflns_used    3572
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.1420
_cell_measurement_theta_min      4.8060
_cell_volume                     1351.88(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.907
_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     89.00 135.00   0.50    0.73    --  107.75 108.00 126.00   92
  2  \w    140.00 166.00   0.50    0.73    --  107.75 108.00 126.00   52
  3  \w     35.00 119.00   0.50    0.18    --   47.20  57.00-150.00  168
  4  \w     73.00 104.00   0.50    0.73    --  107.75-108.00  29.00   62
  5  \w     16.00  80.00   0.50    0.18    --   47.20-108.00  29.00  128
  6  \w    -52.00 -27.00   0.50    0.73    -- -100.00  77.00  90.00   50
  7  \w   -108.00 -69.00   0.50    0.73    -- -100.00  77.00  90.00   78
  8  \w    -64.00 -39.00   0.50    0.73    -- -100.00  57.00  90.00   50
  9  \w    -63.00 -27.00   0.50    0.73    -- -100.00  57.00 -30.00   72
 10  \w    -60.00 -33.00   0.50    0.73    -- -100.00  57.00 -60.00   54
 11  \w    -69.00 -28.00   0.50    0.73    -- -100.00  57.00-120.00   82
 12  \w   -110.00 -31.00   0.50    0.73    -- -100.00 125.00-150.00  158
 13  \w   -106.00 -48.00   0.50    0.73    -- -100.00 108.00 126.00  116
 14  \w    -72.00 -47.00   0.50    0.18    --  -47.20 108.00 126.00   50
 15  \w   -123.00 -89.00   0.50    0.73    -- -100.00 -19.00 -60.00   68
 16  \w   -167.00-128.00   0.50    0.73    -- -100.00 -19.00 -60.00   78
 17  \w   -147.00-121.00   0.50    0.73    -- -100.00-108.00  29.00   52
 18  \w   -171.00-134.00   0.50    0.73    -- -100.00 -77.00  60.00   74
 19  \w   -116.00 -89.00   0.50    0.73    -- -100.00 -77.00  60.00   54
 20  \w    -21.00  22.00   0.50    0.18    --   47.20 -19.00 -90.00   86
 21  \w    -20.00   0.50   0.50    0.18    --   47.20 -37.00 150.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1598853000
_diffrn_orient_matrix_UB_12      -0.0180413000
_diffrn_orient_matrix_UB_13      -0.1197234000
_diffrn_orient_matrix_UB_21      -0.0041144000
_diffrn_orient_matrix_UB_22      -0.0852393000
_diffrn_orient_matrix_UB_23      0.0406856000
_diffrn_orient_matrix_UB_31      -0.1562821000
_diffrn_orient_matrix_UB_32      0.0206018000
_diffrn_orient_matrix_UB_33      0.0627699000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7150
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.009
_diffrn_reflns_theta_min         4.798
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0622
_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^)+(0.1126P)^2^+0.1279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2207
_reflns_number_total             2588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04113h2.cif
_cod_data_source_block           luyi_0510_auto
_cod_depositor_comments          'Adding full bibliography for 7061977.cif.'
_cod_database_code               7061977
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              28338
_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 4.786
_oxdiff_exptl_absorpt_empirical_full_min 0.379