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_7061952
_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         'C18 H17 N3 O2'
_chemical_formula_sum            'C18 H17 N3 O2'
_chemical_formula_weight         307.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 92.243(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4347(6)
_cell_length_b                   5.1670(3)
_cell_length_c                   35.992(2)
_cell_measurement_reflns_used    4781
_cell_measurement_temperature    300.4(2)
_cell_measurement_theta_max      29.2610
_cell_measurement_theta_min      3.9740
_cell_volume                     1567.40(17)
_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      300.4(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.815
_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    -21.00  18.00   0.50  100.00    --   -6.71  58.00 174.00   78
  2  \w    -67.00 -20.00   0.50  100.00    --   -6.71 -58.00  33.00   94
  3  \w    -70.00   0.00   0.50  100.00    --    4.99 -19.00-180.00  140
  4  \w    -22.00  28.00   0.50  100.00    --   -6.71 -99.00  60.00  100
  5  \w    -23.00  26.00   0.50  100.00    --   -6.71 -99.00 -90.00   98
  6  \w     31.00  56.00   0.50  100.00    --   -6.71  58.00 174.00   50
;
_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      0.0204203000
_diffrn_orient_matrix_UB_12      -0.0228822000
_diffrn_orient_matrix_UB_13      0.0190215000
_diffrn_orient_matrix_UB_21      -0.0574363000
_diffrn_orient_matrix_UB_22      0.0920611000
_diffrn_orient_matrix_UB_23      0.0051985000
_diffrn_orient_matrix_UB_31      -0.0580243000
_diffrn_orient_matrix_UB_32      -0.0992261000
_diffrn_orient_matrix_UB_33      0.0004302000
_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  0.0356
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.815
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            14839
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.717
_diffrn_reflns_theta_min         3.248
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90583
_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_colour            'light yellow'
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.2788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2694
_reflns_number_total             3975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04147b2.cif
_cod_data_source_block           lfy_zl_1303_02_n2_auto
_cod_depositor_comments
'Adding full bibliography for 7061950--7061952.cif.'
_cod_original_cell_volume        1567.41(17)
_cod_database_code               7061952
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.987
_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. Restrained distances
 C10-C11 \\sim C10-C11A
 with sigma of 0.02
 C25-C35 \\sim C25-C35A
 with sigma of 0.04
 C10-C35 \\sim C10-C35A
 with sigma of 0.02
 C25-C37 \\sim C25-C37A
 with sigma of 0.02
 C25-C31 \\sim C25-C31A
 with sigma of 0.02
 C10-C31 \\sim C10-C31A
 with sigma of 0.04
 C11-C37 \\sim C11A-C37A
 with sigma of 0.02
 C10-C37 \\sim C10-C37A
 with sigma of 0.04
 C35-C31 \\sim C35A-C31A
 with sigma of 0.02
 C25-C11 \\sim C25-C11A
 with sigma of 0.04
3. Others
 Sof(H25A)=Sof(C11A)=Sof(H11A)=Sof(C37A)=Sof(H37A)=Sof(C31A)=Sof(H31A)=
 Sof(C35A)=Sof(H35A)=1-FVAR(1)
 Sof(H25)=Sof(C11)=Sof(H11)=Sof(C35)=Sof(H35)=Sof(C37)=Sof(H37)=Sof(C31)=
 Sof(H31)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 C32(H32), C30(H30), C26(H26), C34(H34), C25(H25), C25(H25A), C11(H11),
 C35(H35), C37(H37), C31(H31), C11A(H11A), C37A(H37A), C31A(H31A), C35A(H35A)
4.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_shelx_res_checksum              20573
_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 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.882