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_7061950
_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         'C12 H12 N2 O3'
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24
_chemical_name_systematic
'ethyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)acetate'
_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     iterative
_audit_creation_date             2021-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-04 deposited with the CCDC.	2022-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                85.953(9)
_cell_angle_beta                 80.093(9)
_cell_angle_gamma                75.863(7)
_cell_formula_units_Z            2
_cell_length_a                   5.6320(5)
_cell_length_b                   8.3085(7)
_cell_length_c                   12.2276(16)
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2550
_cell_measurement_theta_min      4.2980
_cell_volume                     546.33(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.819
_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      1.00  53.00   1.00    1.00    --   12.53 -99.00 120.00   52
  2  \w    -54.00 -21.00   1.00    1.00    --   12.53 -57.00 120.00   33
  3  \w     12.00  37.00   1.00    1.00    --   12.53 -57.00 120.00   25
  4  \w      2.00  85.00   1.00    1.00    --   12.53  57.00  30.00   83
  5  \w    -11.00  84.00   1.00    1.00    --   12.53  57.00 -90.00   95
;
_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      -0.1204015000
_diffrn_orient_matrix_UB_12      -0.0102377000
_diffrn_orient_matrix_UB_13      0.0224056000
_diffrn_orient_matrix_UB_21      0.0337941000
_diffrn_orient_matrix_UB_22      -0.0128182000
_diffrn_orient_matrix_UB_23      0.0537671000
_diffrn_orient_matrix_UB_31      -0.0408672000
_diffrn_orient_matrix_UB_32      0.0865341000
_diffrn_orient_matrix_UB_33      0.0088236000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4184
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.659
_diffrn_reflns_theta_min         3.384
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0430P)^2^+0.0408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1911
_reflns_number_total             2534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04147b2.cif
_cod_data_source_block           20210827a
_cod_depositor_comments
'Adding full bibliography for 7061950--7061952.cif.'
_cod_database_code               7061950
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1N1O1
_diffrn_oxdiff_digest_frames
;
01944a6fcc01521f6fca6c0adef704e365000329153
;
_diffrn_oxdiff_digest_hkl
;
012dd4278ab5d36066476650dc1b45d67578fb
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              67518
_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.707