Design, Synthesis, and Biological Evaluation of Novel Psoralen-Based 1,3,4-Oxadiazoles as Potent Fungicide Candidates Targeting Pyruvate Kinase.
Dong, Jingyue; Gao, Wei; Li, Kun; Hong, Zeyu; Tang, Liangfu; Han, Lijun; Wang, Zhihong; Fan, Zhijin; Journal of agricultural and food chemistry 70 (2022) 3435–3446; doi:10.1021/acs.jafc.1c07911

data_1566733
_publ_section_title
;
 Design, Synthesis, and Biological Evaluation of Novel Psoralen-Based
 1,3,4-Oxadiazoles as Potent Fungicide Candidates Targeting Pyruvate
 Kinase.
;
_journal_issue                   11
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              3435
_journal_page_last               3446
_journal_paper_doi               10.1021/acs.jafc.1c07911
_journal_volume                  70
_journal_year                    2022
_chemical_formula_moiety         'C32 H28 N2 O5 S'
_chemical_formula_sum            'C32 H28 N2 O5 S'
_chemical_formula_weight         552.62
_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             2021-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                102.141(6)
_cell_angle_beta                 94.257(5)
_cell_angle_gamma                104.092(5)
_cell_formula_units_Z            2
_cell_length_a                   7.2319(4)
_cell_length_b                   11.7336(7)
_cell_length_c                   16.6396(12)
_cell_measurement_reflns_used    6116
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      30.7410
_cell_measurement_theta_min      1.8440
_cell_volume                     1327.08(15)
_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                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.897
_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   -115.00  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0402844000
_diffrn_orient_matrix_UB_12      0.0626585000
_diffrn_orient_matrix_UB_13      0.0174612000
_diffrn_orient_matrix_UB_21      -0.0184247000
_diffrn_orient_matrix_UB_22      0.0122800000
_diffrn_orient_matrix_UB_23      -0.0393407000
_diffrn_orient_matrix_UB_31      -0.0918998000
_diffrn_orient_matrix_UB_32      0.0060820000
_diffrn_orient_matrix_UB_33      0.0090810000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.1094
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20106
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.852
_diffrn_reflns_theta_min         1.841
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0094(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         8855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0704
_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/[\s^2^(Fo^2^)+(0.0595P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4873
_reflns_number_total             8855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf1c07911_si_003.cif
_cod_data_source_block           r20210709a
_cod_database_code               1566733
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.965
_reflns_odcompleteness_completeness 99.94
_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
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C15(H15), C17(H17), C24(H24),
 C25(H25), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
;
_shelx_res_checksum              90530
_shelx_hkl_checksum              15179
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.922
_oxdiff_exptl_absorpt_empirical_full_min 0.688