Novel fungicidal phenylethanol derivatives linking a trifluoromethyl pyrazole pharmacophore: design, synthesis, crystal structure, and biology evaluation
Tai, Lang; Sun, Sheng-Xin; Yue, Kai; Chai, Jian-Qi; Hou, Shuai-Tao; Dai, Guang-Yu; Yang, Chun-Long; Chen, Min; New Journal of Chemistry 47 (2023) 12850–12860; doi:10.1039/D3NJ02234J

data_7062572
_publ_section_title
;
 Novel fungicidal phenylethanol derivatives linking a trifluoromethyl
 pyrazole pharmacophore: design, synthesis, crystal structure, and biology
 evaluation
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12850
_journal_page_last               12860
_journal_paper_doi               10.1039/D3NJ02234J
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C13 H11 F5 N2 O2'
_chemical_formula_sum            'C13 H11 F5 N2 O2'
_chemical_formula_weight         322.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-02-27 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.311(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2006(5)
_cell_length_b                   13.3581(8)
_cell_length_c                   12.1780(8)
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.7970
_cell_measurement_theta_min      3.3450
_cell_volume                     1334.01(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -59.00  39.00   1.00    1.35    --   12.05 -57.00 150.00   98
  2  \w    -17.00  81.00   1.00    1.35    --   12.05  77.00  60.00   98
  3  \w    -11.00  82.00   1.00    1.35    --   12.05  57.00 -60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0087436000
_diffrn_orient_matrix_UB_12      0.0526807000
_diffrn_orient_matrix_UB_13      -0.0053676000
_diffrn_orient_matrix_UB_21      0.0130361000
_diffrn_orient_matrix_UB_22      0.0040897000
_diffrn_orient_matrix_UB_23      0.0574529000
_diffrn_orient_matrix_UB_31      0.0849679000
_diffrn_orient_matrix_UB_32      -0.0060068000
_diffrn_orient_matrix_UB_33      -0.0077273000
_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  0.0259
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8513
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.263
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+1.1353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2054
_reflns_number_total             2358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02234j2.cif
_cod_data_source_block           0127
_cod_database_code               7062572
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.93
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              94591
_shelx_hkl_checksum              71503
_olex2_date_sample_data_collection 2021-11-17
_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 0.721