Formal [4+1] cyclization of (thio/imido)hydrazides and ethyl 3,3,3-trifluoropropanoate: unified synthesis of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles
Zhao, Lan; Xu, Jun; Ma, Jun; Yin, Guangwei; Li, Fangyi; Suo, Tongchuan; Wang, Chunhua; New Journal of Chemistry 46 (2022) 20755–20759; doi:10.1039/D2NJ04147B

data_7061951
_publ_section_title
;
 Formal [4+1] cyclization of (thio/imido)hydrazides and ethyl
 3,3,3-trifluoropropanoate: unified synthesis of 1,3,4-oxadiazoles,
 1,3,4-thiadiazoles and 1,2,4-triazoles
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20755
_journal_page_last               20759
_journal_paper_doi               10.1039/D2NJ04147B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C16 H14 N2 O2 S'
_chemical_formula_sum            'C16 H14 N2 O2 S'
_chemical_formula_weight         298.35
_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             2022-06-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-12 deposited with the CCDC.	2022-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                106.819(4)
_cell_angle_beta                 100.376(4)
_cell_angle_gamma                93.807(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7462(4)
_cell_length_b                   9.2543(4)
_cell_length_c                   10.7494(5)
_cell_measurement_reflns_used    4653
_cell_measurement_temperature    300.14(10)
_cell_measurement_theta_max      30.3390
_cell_measurement_theta_min      3.6170
_cell_volume                     719.78(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.14(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.783
_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     -7.00  20.00   0.50    5.00    --    4.99  57.00  30.00   54
  2  \w     52.00  78.00   0.50    5.00    --    4.99  57.00  30.00   52
  3  \w    -22.00  66.00   0.50    5.00    --   -6.71  57.00 150.00  176
  4  \w    -72.00 -26.00   0.50    5.00    --   -6.71 -57.00 150.00   92
  5  \w    -24.00   6.00   0.50    5.00    --   -6.71 -57.00 150.00   60
  6  \w    -23.00  28.00   0.50    5.00    --   -6.71 -99.00 -30.00  102
  7  \w    -23.00   3.00   0.50    5.00    --   -6.71 -99.00  90.00   52
  8  \w     -9.00  69.00   0.50    5.00    --   -6.71  19.00 -90.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0501599000
_diffrn_orient_matrix_UB_12      -0.0572915000
_diffrn_orient_matrix_UB_13      -0.0286953000
_diffrn_orient_matrix_UB_21      -0.0568320000
_diffrn_orient_matrix_UB_22      -0.0136194000
_diffrn_orient_matrix_UB_23      -0.0629130000
_diffrn_orient_matrix_UB_31      0.0553099000
_diffrn_orient_matrix_UB_32      0.0551972000
_diffrn_orient_matrix_UB_33      -0.0136662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.783
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9033
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.912
_diffrn_reflns_theta_min         3.515
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             312
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0530P)^2^+0.0335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2468
_reflns_number_total             3569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04147b2.cif
_cod_data_source_block           lfy_zl_1303_02_s_auto
_cod_depositor_comments
'Adding full bibliography for 7061950--7061952.cif.'
_cod_database_code               7061951
_shelx_shelxl_version_number     2018/3
_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), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C27(H27), C28(H28), C34(H34), C20(H20), C10(H10), C16(H16)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              261
_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 1.646
_oxdiff_exptl_absorpt_empirical_full_min 0.611