Design, Synthesis and Evaluation of Antifungal Activity of Novel Pyrazole-thiazole Carboxamides as Succinate Dehydrogenase Inhibitors.
Yu, Bin; Zhou, Shuang; Cao, Lixin; Hao, Zesheng; Yang, Dongyan; Guo, Xiaofeng; Zhang, Nailou; Bakulev, Vasiliy A.; Fan, Zhijin; Journal of agricultural and food chemistry  (2020) –; doi:10.1021/acs.jafc.0c00062

data_1558429
_publ_section_title
;
 Design, Synthesis and Evaluation of Antifungal Activity of Novel
 Pyrazole-thiazole Carboxamides as Succinate Dehydrogenase Inhibitors.
;
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_paper_doi               10.1021/acs.jafc.0c00062
_journal_year                    2020
_chemical_formula_moiety         'C15 H11 Br F2 N4 O S'
_chemical_formula_sum            'C15 H11 Br F2 N4 O S'
_chemical_formula_weight         413.25
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-10-19 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                92.048(2)
_cell_angle_beta                 106.633(2)
_cell_angle_gamma                102.379(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0375(2)
_cell_length_b                   9.3645(2)
_cell_length_c                   12.0386(3)
_cell_measurement_reflns_used    10027
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      28.6620
_cell_measurement_theta_min      3.6600
_cell_volume                     843.44(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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    -84.00  94.00   0.50    1.57    --    5.00  45.00 174.00  356
  2  \w    -97.00  81.00   0.50    1.57    --   -8.10  45.00  30.00  356
  3  \w    -18.00  19.00   0.50    1.57    --   -8.10  45.00 150.00   74
  4  \w    -16.00  81.00   0.50    1.57    --   -8.10  45.00  90.00  194
  5  \w     20.00  51.00   0.50    1.57    --   -8.10  45.00   0.00   62
  6  \w    -78.00 -22.00   0.50    1.57    --   -8.10  45.00 150.00  112
  7  \w    -97.00 -33.00   0.50    1.57    --   -8.10  45.00  90.00  128
  8  \w    -51.00 -25.00   0.50    1.57    --   -8.10  45.00  30.00   52
  9  \w    -97.00  81.00   0.50    1.57    --   -8.10  45.00 179.43  356
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0507965000
_diffrn_orient_matrix_UB_12      -0.0050455000
_diffrn_orient_matrix_UB_13      0.0397495000
_diffrn_orient_matrix_UB_21      0.0773145000
_diffrn_orient_matrix_UB_22      -0.0014977000
_diffrn_orient_matrix_UB_23      0.0463073000
_diffrn_orient_matrix_UB_31      0.0204686000
_diffrn_orient_matrix_UB_32      0.0777895000
_diffrn_orient_matrix_UB_33      0.0098988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23620
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         3.552
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.627
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4163
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.5293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3295
_reflns_number_total             4163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf0c00062_si_001.cif
_cod_data_source_block           m20190311b
_cod_database_code               1558429
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H11BrF2N4OS
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3-C5 \\sim C3-C5A
 with sigma of 0.01
 C5-F1 \\sim C5-F2 \\sim C5A-F1A \\sim C5A-F2A
 with sigma of 0.01
 C3-F1 \\sim C3-F2 \\sim C3-F1A \\sim C3-F2A
 with sigma of 0.01
 F1-F2 \\sim F1A-F2A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(F1A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C5) = Uanis(C5A)
4. Others
 Sof(C5A)=Sof(H5A)=Sof(F1A)=Sof(F2A)=1-FVAR(1)
 Sof(C5)=Sof(H5)=Sof(F1)=Sof(F2)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C5A(H5A)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C11(H11), C13(H13), C14(H14), C15(H15)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              69397
_shelx_hkl_checksum              1655
_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 2.098
_oxdiff_exptl_absorpt_empirical_full_min 0.609