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_1566734
_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         'C29 H22 N2 O4 S'
_chemical_formula_sum            'C29 H22 N2 O4 S'
_chemical_formula_weight         494.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6146(3)
_cell_length_b                   15.9025(4)
_cell_length_c                   29.7245(7)
_cell_measurement_reflns_used    18726
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.1020
_cell_measurement_theta_min      2.5510
_cell_volume                     4544.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_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 0.997
_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   -120.00  60.00   0.50    5.00    --  -30.00  45.00   0.00  360
  2  \w   -120.00  60.00   0.50    5.00    --  -30.00  45.00  90.00  360
  3  \w   -120.00  60.00   0.50    5.00    --  -30.00  45.00 180.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0108525000
_diffrn_orient_matrix_UB_12      0.0441007000
_diffrn_orient_matrix_UB_13      0.0007265000
_diffrn_orient_matrix_UB_21      0.0012665000
_diffrn_orient_matrix_UB_22      0.0014925000
_diffrn_orient_matrix_UB_23      -0.0238434000
_diffrn_orient_matrix_UB_31      -0.0729576000
_diffrn_orient_matrix_UB_32      -0.0065426000
_diffrn_orient_matrix_UB_33      -0.0005319000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            43995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.523
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66117
_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    1.446
_exptl_crystal_description       needle
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0515P)^2^+2.4579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4646
_reflns_number_total             5625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf1c07911_si_002.cif
_cod_data_source_block           r20210602a
_cod_database_code               1566734
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C29H22N2O4S
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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:
 C3(H3A,H3B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C24(H24), C26(H26), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C29(H29A,H29B,H29C)
;
_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 1.924
_oxdiff_exptl_absorpt_empirical_full_min 0.698