#------------------------------------------------------------------------------
#$Date: 2021-12-04 02:55:52 +0200 (Sat, 04 Dec 2021) $
#$Revision: 271075 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/55/1565500.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_1565500
loop_
_publ_author_name
'Yang, Zihui'
'Sun, Yue'
'Liu, Qingsong'
'Li, Aliang'
'Wang, Wenyan'
'Gu, Wen'
_publ_section_title
;
 Design, Synthesis, and Antifungal Activity of Novel
 Thiophene/Furan-1,3,4-Oxadiazole Carboxamides as Potent Succinate
 Dehydrogenase Inhibitors.
;
_journal_issue                   45
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              13373
_journal_page_last               13385
_journal_paper_doi               10.1021/acs.jafc.1c03857
_journal_volume                  69
_journal_year                    2021
_chemical_formula_sum            'C15 H10 F3 N3 O2 S'
_chemical_formula_weight         353.32
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-02-06 # Formatted by publCIF

;
_cell_angle_alpha                105.521(2)
_cell_angle_beta                 92.920(2)
_cell_angle_gamma                102.470(2)
_cell_formula_units_Z            2
_cell_length_a                   5.60030(10)
_cell_length_b                   10.1540(3)
_cell_length_c                   13.8448(3)
_cell_measurement_reflns_used    11399
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.3101
_cell_measurement_theta_min      3.3400
_cell_volume                     735.72(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16027
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.226
_diffrn_reflns_theta_min         3.335
_exptl_absorpt_coefficient_mu    2.432
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.31102
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.206
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0128(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0543
_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)+(0.1000P)²+1.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2767
_reflns_number_total             2850
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jf1c03857_si_002.cif
_cod_data_source_block           X
_cod_database_code               1565500
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.642
_shelx_estimated_absorpt_t_max   0.793
_publcif_funding_html
;
;
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
S S 0.28220(12) 0.83368(7) 0.22808(5) 0.0291(2) Uani 1 1 d . . . . .
O1 O -0.0256(3) 1.14957(16) 0.34543(12) 0.0183(4) Uani 1 1 d . . . . .
F1 F -0.0883(4) 1.80988(19) 0.96860(14) 0.0493(5) Uani 1 1 d . . . . .
N1 N -0.0975(4) 0.9361(2) 0.36638(15) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.5021(5) 0.8846(3) 0.15649(19) 0.0266(6) Uani 1 1 d . . . . .
H1A H 0.5960 0.8259 0.1224 0.032 Uiso 1 1 calc R U . . .
O2 O -0.2635(3) 1.36066(17) 0.41921(13) 0.0224(4) Uani 1 1 d . . . . .
N2 N -0.2557(4) 1.0101(2) 0.42035(15) 0.0191(4) Uani 1 1 d . . . . .
F2 F -0.1410(4) 1.6322(2) 1.02559(12) 0.0483(5) Uani 1 1 d . . . . .
C2 C 0.5268(5) 1.0201(3) 0.1542(2) 0.0281(6) Uani 1 1 d . U . . .
H2B H 0.6419 1.0614 0.1184 0.034 Uiso 1 1 calc R U . . .
F3 F 0.1773(3) 1.6872(2) 0.95081(13) 0.0441(5) Uani 1 1 d . . . . .
N3 N -0.4860(4) 1.2299(2) 0.50996(15) 0.0182(4) Uani 1 1 d . . . . .
H3A H -0.5205 1.1489 0.5211 0.022 Uiso 1 1 calc R U . . .
C3 C 0.3658(4) 1.0955(3) 0.20997(17) 0.0206(5) Uani 1 1 d . U . . .
H3B H 0.3558 1.1873 0.2150 0.025 Uiso 1 1 calc R U . . .
C4 C 0.2187(4) 0.9962(2) 0.25787(17) 0.0206(5) Uani 1 1 d . U . . .
C5 C 0.0324(4) 1.0223(2) 0.32359(17) 0.0177(5) Uani 1 1 d . . . . .
C6 C -0.2076(4) 1.1327(2) 0.40528(17) 0.0166(5) Uani 1 1 d . . . . .
C7 C -0.3226(4) 1.2532(2) 0.44562(17) 0.0179(5) Uani 1 1 d . . . . .
C8 C -0.6078(4) 1.3382(2) 0.56198(17) 0.0182(5) Uani 1 1 d . . . . .
H8A H -0.7721 1.2936 0.5724 0.022 Uiso 1 1 calc R U . . .
H8B H -0.6237 1.3990 0.5198 0.022 Uiso 1 1 calc R U . . .
C9 C -0.4661(4) 1.4261(2) 0.66280(17) 0.0177(5) Uani 1 1 d . . . . .
C10 C -0.5745(4) 1.4310(2) 0.75181(18) 0.0211(5) Uani 1 1 d . . . . .
H10A H -0.7353 1.3801 0.7491 0.025 Uiso 1 1 calc R U . . .
C11 C -0.4446(5) 1.5108(3) 0.84430(19) 0.0230(5) Uani 1 1 d . . . . .
H11A H -0.5183 1.5138 0.9033 0.028 Uiso 1 1 calc R U . . .
C12 C -0.2032(4) 1.5865(2) 0.84851(18) 0.0206(5) Uani 1 1 d . . . . .
C13 C -0.0929(4) 1.5826(2) 0.75997(18) 0.0203(5) Uani 1 1 d . . . . .
H13A H 0.0682 1.6332 0.7627 0.024 Uiso 1 1 calc R U . . .
C14 C -0.2243(4) 1.5031(2) 0.66836(18) 0.0193(5) Uani 1 1 d . . . . .
H14A H -0.1507 1.5006 0.6094 0.023 Uiso 1 1 calc R U . . .
C15 C -0.0644(5) 1.6770(3) 0.94738(19) 0.0248(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C1 S C4 91.11(13) . . ?
C6 O1 C5 102.16(17) . . ?
C5 N1 N2 105.61(19) . . ?
C2 C1 S 113.1(2) . . ?
C2 C1 H1A 123.4 . . ?
S C1 H1A 123.4 . . ?
C6 N2 N1 106.33(19) . . ?
C1 C2 C3 116.3(2) . . ?
C1 C2 H2B 121.8 . . ?
C3 C2 H2B 121.8 . . ?
C7 N3 C8 121.93(19) . . ?
C7 N3 H3A 119.0 . . ?
C8 N3 H3A 119.0 . . ?
C2 C3 C4 105.3(2) . . ?
C2 C3 H3B 127.3 . . ?
C4 C3 H3B 127.3 . . ?
C5 C4 C3 127.2(2) . . ?
C5 C4 S 118.70(19) . . ?
C3 C4 S 114.09(18) . . ?
N1 C5 O1 112.9(2) . . ?
N1 C5 C4 127.7(2) . . ?
O1 C5 C4 119.4(2) . . ?
N2 C6 O1 113.0(2) . . ?
N2 C6 C7 128.6(2) . . ?
O1 C6 C7 118.39(19) . . ?
O2 C7 N3 126.2(2) . . ?
O2 C7 C6 120.0(2) . . ?
N3 C7 C6 113.74(19) . . ?
N3 C8 C9 111.87(19) . . ?
N3 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N3 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C14 118.9(2) . . ?
C10 C9 C8 120.5(2) . . ?
C14 C9 C8 120.6(2) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11A 120.1 . . ?
C12 C11 H11A 120.1 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 C15 120.2(2) . . ?
C13 C12 C15 119.6(2) . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C13 C14 C9 121.0(2) . . ?
C13 C14 H14A 119.5 . . ?
C9 C14 H14A 119.5 . . ?
F3 C15 F2 107.3(2) . . ?
F3 C15 F1 105.1(2) . . ?
F2 C15 F1 105.1(2) . . ?
F3 C15 C12 113.1(2) . . ?
F2 C15 C12 113.0(2) . . ?
F1 C15 C12 112.6(2) . . ?
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
S C1 1.700(3) . ?
S C4 1.710(2) . ?
O1 C6 1.357(3) . ?
O1 C5 1.360(3) . ?
F1 C15 1.340(3) . ?
N1 C5 1.301(3) . ?
N1 N2 1.401(3) . ?
C1 C2 1.362(4) . ?
C1 H1A 0.9300 . ?
O2 C7 1.226(3) . ?
N2 C6 1.290(3) . ?
F2 C15 1.338(3) . ?
C2 C3 1.431(3) . ?
C2 H2B 0.9300 . ?
F3 C15 1.333(3) . ?
N3 C7 1.338(3) . ?
N3 C8 1.464(3) . ?
N3 H3A 0.8600 . ?
C3 C4 1.480(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.440(3) . ?
C6 C7 1.495(3) . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.395(3) . ?
C9 C14 1.397(3) . ?
C10 C11 1.386(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.393(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.396(3) . ?
C12 C15 1.494(3) . ?
C13 C14 1.379(3) . ?
C13 H13A 0.9300 . ?
C14 H14A 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
C4 S C1 C2 -0.4(2) . . . . ?
C5 N1 N2 C6 0.1(2) . . . . ?
S C1 C2 C3 -0.7(3) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C3 C4 C5 178.9(2) . . . . ?
C2 C3 C4 S -1.9(2) . . . . ?
C1 S C4 C5 -179.32(19) . . . . ?
C1 S C4 C3 1.40(19) . . . . ?
N2 N1 C5 O1 0.4(2) . . . . ?
N2 N1 C5 C4 -178.6(2) . . . . ?
C6 O1 C5 N1 -0.8(2) . . . . ?
C6 O1 C5 C4 178.4(2) . . . . ?
C3 C4 C5 N1 -179.7(2) . . . . ?
S C4 C5 N1 1.1(3) . . . . ?
C3 C4 C5 O1 1.2(3) . . . . ?
S C4 C5 O1 -177.94(15) . . . . ?
N1 N2 C6 O1 -0.6(2) . . . . ?
N1 N2 C6 C7 -179.8(2) . . . . ?
C5 O1 C6 N2 0.8(2) . . . . ?
C5 O1 C6 C7 -179.91(19) . . . . ?
C8 N3 C7 O2 -3.3(4) . . . . ?
C8 N3 C7 C6 176.44(19) . . . . ?
N2 C6 C7 O2 -176.1(2) . . . . ?
O1 C6 C7 O2 4.8(3) . . . . ?
N2 C6 C7 N3 4.1(3) . . . . ?
O1 C6 C7 N3 -175.04(18) . . . . ?
C7 N3 C8 C9 -91.0(2) . . . . ?
N3 C8 C9 C10 -119.9(2) . . . . ?
N3 C8 C9 C14 59.7(3) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 C11 179.6(2) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C10 C11 C12 C15 177.8(2) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C15 C12 C13 C14 -177.6(2) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C10 C9 C14 C13 0.2(3) . . . . ?
C8 C9 C14 C13 -179.4(2) . . . . ?
C11 C12 C15 F3 149.5(2) . . . . ?
C13 C12 C15 F3 -32.9(3) . . . . ?
C11 C12 C15 F2 27.4(3) . . . . ?
C13 C12 C15 F2 -155.1(2) . . . . ?
C11 C12 C15 F1 -91.5(3) . . . . ?
C13 C12 C15 F1 86.0(3) . . . . ?
loop_
_publcif_info_cif.paper_type
?
