#------------------------------------------------------------------------------
#$Date: 2023-01-06 11:50:53 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/19/7061951.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7061951
loop_
_publ_author_name
'Zhao, Lan'
'Xu, Jun'
'Ma, Jun'
'Yin, Guangwei'
'Li, Fangyi'
'Suo, Tongchuan'
'Wang, Chunhua'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  20.00   0.50    5.00    --    4.99  57.00  30.00   54
  2  ω     52.00  78.00   0.50    5.00    --    4.99  57.00  30.00   52
  3  ω    -22.00  66.00   0.50    5.00    --   -6.71  57.00 150.00  176
  4  ω    -72.00 -26.00   0.50    5.00    --   -6.71 -57.00 150.00   92
  5  ω    -24.00   6.00   0.50    5.00    --   -6.71 -57.00 150.00   60
  6  ω    -23.00  28.00   0.50    5.00    --   -6.71 -99.00 -30.00  102
  7  ω    -23.00   3.00   0.50    5.00    --   -6.71 -99.00  90.00   52
  8  ω     -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       'ω 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/[σ²(Fo²)+(0.0530P)²+0.0335P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S35 S 0.67397(5) 0.33823(5) 0.45716(4) 0.05424(15) Uani 1 1 d . . . . .
O29 O 0.41589(15) -0.11692(12) 0.16440(11) 0.0623(3) Uani 1 1 d . . . . .
O2 O 0.58786(18) 0.01358(14) 0.36179(12) 0.0747(4) Uani 1 1 d . . . . .
N31 N 0.5853(2) 0.40433(15) 0.24362(13) 0.0621(4) Uani 1 1 d . . . . .
N7 N 0.6763(2) 0.53612(15) 0.33552(13) 0.0632(4) Uani 1 1 d . . . . .
C15 C 0.57317(19) 0.29242(17) 0.29225(14) 0.0478(3) Uani 1 1 d . . . . .
C33 C 0.72816(19) 0.51942(17) 0.45188(15) 0.0473(3) Uani 1 1 d . . . . .
C22 C 0.82644(19) 0.64552(17) 0.56699(14) 0.0477(3) Uani 1 1 d . . . . .
C24 C 0.5016(2) 0.00860(18) 0.25582(16) 0.0541(4) Uani 1 1 d . . . . .
C3 C 0.8353(2) 0.79151(18) 0.56084(15) 0.0503(3) Uani 1 1 d . . . . .
H3 H 0.775255 0.810491 0.485256 0.060 Uiso 1 1 calc R U . . .
C19 C 0.93403(19) 0.91361(18) 0.66713(15) 0.0501(3) Uani 1 1 d . . . . .
C9 C 0.4720(2) 0.14353(17) 0.20710(15) 0.0534(4) Uani 1 1 d . . . . .
H9A H 0.501125 0.121529 0.119979 0.064 Uiso 1 1 calc R U . . .
H9B H 0.346982 0.154357 0.195985 0.064 Uiso 1 1 calc R U . . .
C25 C 1.0247(2) 0.88316(19) 0.78253(15) 0.0533(4) Uani 1 1 d . . . . .
C27 C 0.9142(2) 0.61699(19) 0.68368(16) 0.0562(4) Uani 1 1 d . . . . .
H27 H 0.906681 0.518329 0.689041 0.067 Uiso 1 1 calc R U . . .
C11 C 0.4257(3) -0.2573(2) 0.1998(2) 0.0704(5) Uani 1 1 d . . . . .
H11A H 0.385443 -0.246587 0.281993 0.084 Uiso 1 1 calc R U . . .
H11B H 0.546820 -0.280206 0.212186 0.084 Uiso 1 1 calc R U . . .
C28 C 1.0090(2) 0.7326(2) 0.78739(16) 0.0598(4) Uani 1 1 d . . . . .
H28 H 1.064945 0.712029 0.863383 0.072 Uiso 1 1 calc R U . . .
C34 C 0.9503(2) 1.06438(19) 0.66187(18) 0.0623(4) Uani 1 1 d . . . . .
H34 H 0.890649 1.086241 0.587586 0.075 Uiso 1 1 calc R U . . .
C20 C 1.1269(2) 1.0053(2) 0.88761(17) 0.0650(4) Uani 1 1 d . . . . .
H20 H 1.185188 0.986964 0.964058 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3111(3) -0.3815(2) 0.0900(2) 0.0779(5) Uani 1 1 d . . . . .
H12A H 0.351514 -0.390817 0.009051 0.117 Uiso 1 1 calc R U . . .
H12B H 0.191288 -0.358511 0.079369 0.117 Uiso 1 1 calc R U . . .
H12C H 0.316324 -0.475557 0.110687 0.117 Uiso 1 1 calc R U . . .
C10 C 1.0524(3) 1.1782(2) 0.7645(2) 0.0720(5) Uani 1 1 d . . . . .
H10 H 1.063503 1.276772 0.759039 0.086 Uiso 1 1 calc R U . . .
C16 C 1.1413(3) 1.1479(2) 0.8788(2) 0.0739(5) Uani 1 1 d . . . . .
H16 H 1.210190 1.226482 0.948481 0.089 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 S35 C33 87.29(7) . . ?
C24 O29 C11 116.12(13) . . ?
C15 N31 N7 112.96(12) . . ?
C33 N7 N31 112.23(12) . . ?
N31 C15 S35 113.71(12) . . ?
N31 C15 C9 119.62(13) . . ?
C9 C15 S35 126.62(11) . . ?
N7 C33 S35 113.79(12) . . ?
N7 C33 C22 122.18(13) . . ?
C22 C33 S35 124.03(11) . . ?
C3 C22 C33 119.84(13) . . ?
C3 C22 C27 119.45(15) . . ?
C27 C22 C33 120.71(13) . . ?
O29 C24 C9 109.67(13) . . ?
O2 C24 O29 125.03(15) . . ?
O2 C24 C9 125.29(16) . . ?
C22 C3 H3 119.4 . . ?
C22 C3 C19 121.17(14) . . ?
C19 C3 H3 119.4 . . ?
C3 C19 C25 118.87(14) . . ?
C3 C19 C34 122.42(14) . . ?
C34 C19 C25 118.69(15) . . ?
C15 C9 C24 116.75(13) . . ?
C15 C9 H9A 108.1 . . ?
C15 C9 H9B 108.1 . . ?
C24 C9 H9A 108.1 . . ?
C24 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C28 C25 C19 118.63(15) . . ?
C28 C25 C20 122.64(15) . . ?
C20 C25 C19 118.73(16) . . ?
C22 C27 H27 119.8 . . ?
C28 C27 C22 120.42(15) . . ?
C28 C27 H27 119.8 . . ?
O29 C11 H11A 110.1 . . ?
O29 C11 H11B 110.1 . . ?
O29 C11 C12 107.94(14) . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
C25 C28 H28 119.3 . . ?
C27 C28 C25 121.42(14) . . ?
C27 C28 H28 119.3 . . ?
C19 C34 H34 119.7 . . ?
C10 C34 C19 120.66(17) . . ?
C10 C34 H34 119.7 . . ?
C25 C20 H20 119.5 . . ?
C16 C20 C25 121.08(17) . . ?
C16 C20 H20 119.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C34 C10 H10 119.7 . . ?
C34 C10 C16 120.51(17) . . ?
C16 C10 H10 119.7 . . ?
C20 C16 C10 120.32(18) . . ?
C20 C16 H16 119.8 . . ?
C10 C16 H16 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S35 C15 1.7188(15) . ?
S35 C33 1.7209(15) . ?
O29 C24 1.326(2) . ?
O29 C11 1.4584(18) . ?
O2 C24 1.1991(19) . ?
N31 N7 1.3777(19) . ?
N31 C15 1.2934(19) . ?
N7 C33 1.2995(19) . ?
C15 C9 1.489(2) . ?
C33 C22 1.476(2) . ?
C22 C3 1.369(2) . ?
C22 C27 1.419(2) . ?
C24 C9 1.503(2) . ?
C3 H3 0.9300 . ?
C3 C19 1.411(2) . ?
C19 C25 1.423(2) . ?
C19 C34 1.411(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C25 C28 1.407(2) . ?
C25 C20 1.414(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.356(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.484(3) . ?
C28 H28 0.9300 . ?
C34 H34 0.9300 . ?
C34 C10 1.362(3) . ?
C20 H20 0.9300 . ?
C20 C16 1.349(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C16 1.408(3) . ?
C16 H16 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S35 C15 C9 C24 -18.2(2) . . . . ?
S35 C33 C22 C3 -167.92(11) . . . . ?
S35 C33 C22 C27 13.0(2) . . . . ?
O29 C24 C9 C15 -174.27(12) . . . . ?
O2 C24 C9 C15 6.5(2) . . . . ?
N31 N7 C33 S35 1.55(18) . . . . ?
N31 N7 C33 C22 -179.24(12) . . . . ?
N31 C15 C9 C24 164.49(14) . . . . ?
N7 N31 C15 S35 -0.21(18) . . . . ?
N7 N31 C15 C9 177.44(13) . . . . ?
N7 C33 C22 C3 13.0(2) . . . . ?
N7 C33 C22 C27 -166.15(14) . . . . ?
C15 S35 C33 N7 -1.38(12) . . . . ?
C15 S35 C33 C22 179.43(12) . . . . ?
C15 N31 N7 C33 -0.9(2) . . . . ?
C33 S35 C15 N31 0.87(12) . . . . ?
C33 S35 C15 C9 -176.58(13) . . . . ?
C33 C22 C3 C19 -177.46(12) . . . . ?
C33 C22 C27 C28 177.85(13) . . . . ?
C22 C3 C19 C25 -0.3(2) . . . . ?
C22 C3 C19 C34 177.90(13) . . . . ?
C22 C27 C28 C25 -0.5(2) . . . . ?
C24 O29 C11 C12 175.63(14) . . . . ?
C3 C22 C27 C28 -1.3(2) . . . . ?
C3 C19 C25 C28 -1.4(2) . . . . ?
C3 C19 C25 C20 178.51(13) . . . . ?
C3 C19 C34 C10 -177.42(14) . . . . ?
C19 C25 C28 C27 1.8(2) . . . . ?
C19 C25 C20 C16 -1.0(2) . . . . ?
C19 C34 C10 C16 -1.1(3) . . . . ?
C25 C19 C34 C10 0.8(2) . . . . ?
C25 C20 C16 C10 0.7(3) . . . . ?
C27 C22 C3 C19 1.7(2) . . . . ?
C11 O29 C24 O2 1.8(2) . . . . ?
C11 O29 C24 C9 -177.45(13) . . . . ?
C28 C25 C20 C16 178.93(16) . . . . ?
C34 C19 C25 C28 -179.70(14) . . . . ?
C34 C19 C25 C20 0.2(2) . . . . ?
C34 C10 C16 C20 0.3(3) . . . . ?
C20 C25 C28 C27 -178.09(14) . . . . ?
