Discovery of Novel Pyrazole Amides as Potent Fungicide Candidates and Evaluation of Their Mode of Action.
Sun, Susu; Chen, Lai; Huo, Jingqian; Wang, Ying; Kou, Song; Yuan, Shitao; Fu, Yining; Zhang, Jinlin; Journal of agricultural and food chemistry 70 (2022) 3447–3457; doi:10.1021/acs.jafc.2c00092

data_1566735
_publ_section_title
;
 Discovery of Novel Pyrazole Amides as Potent Fungicide Candidates and
 Evaluation of Their Mode of Action.
;
_journal_issue                   11
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              3447
_journal_page_last               3457
_journal_paper_doi               10.1021/acs.jafc.2c00092
_journal_volume                  70
_journal_year                    2022
_chemical_formula_moiety         'C22 H22 Cl F3 N4 O'
_chemical_formula_sum            'C22 H22 Cl F3 N4 O'
_chemical_formula_weight         450.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.868(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.4942(5)
_cell_length_b                   8.0752(2)
_cell_length_c                   27.7657(6)
_cell_measurement_reflns_used    14750
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.1220
_cell_measurement_theta_min      3.6900
_cell_volume                     4261.09(18)
_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      113.15
_diffrn_detector                 pilatus
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.878
_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     69.00  94.00   0.50    6.00    --    5.00  45.00   0.00   50
  2  \w    -13.00  28.00   0.50    6.00    --  -13.60  45.00  30.00   82
  3  \w   -102.00  75.00   0.50    6.00    --  -13.60  45.00 120.00  354
  4  \w      7.00  75.00   0.50    6.00    --  -13.60  45.00   0.00  136
  5  \w    -61.00 -34.00   0.50    6.00    --  -13.60  45.00  60.00   54
  6  \w      2.00  65.00   0.50    6.00    --  -13.60  45.00  60.00  126
  7  \w    -56.00 -31.00   0.50    6.00    --  -13.60  45.00  30.00   50
  8  \w    -38.00 -12.00   0.50    6.00    --  -13.60  45.00  90.00   52
  9  \w   -103.00  75.00   0.50    6.00    --  -13.60  45.00 169.21  356
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku 007hf'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0040065000
_diffrn_orient_matrix_UB_12      -0.0802309000
_diffrn_orient_matrix_UB_13      0.0094020000
_diffrn_orient_matrix_UB_21      -0.0066614000
_diffrn_orient_matrix_UB_22      -0.0325604000
_diffrn_orient_matrix_UB_23      -0.0243164000
_diffrn_orient_matrix_UB_31      0.0365204000
_diffrn_orient_matrix_UB_32      -0.0146993000
_diffrn_orient_matrix_UB_33      0.0025594000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            27323
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.051
_diffrn_reflns_theta_min         3.396
_diffrn_source                   Rotating-anode
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0418P)^2^+5.0060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4506
_reflns_number_total             5003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf2c00092_si_002.cif
_cod_data_source_block           m20210315a
_cod_database_code               1566735
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 98.65
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N4(H4)
2.b Ternary CH refined with riding coordinates:
 C22(H22)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              24148
_shelx_hkl_checksum              55319
_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 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.843