Quassinoids with Inhibitory Activities against Plant Fungal Pathogens from <i>Picrasma javanica</i>.
Chen, Jian-Jun; Bai, Wei; Lu, Yu-Bo; Feng, Zi-Yun; Gao, Kun; Yue, Jian-Min; Journal of natural products  (2021) –; doi:10.1021/acs.jnatprod.1c00096

data_1563902
_publ_section_title
;
 Quassinoids with Inhibitory Activities against Plant Fungal Pathogens
 from <i>Picrasma javanica</i>.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.1c00096
_journal_year                    2021
_chemical_absolute_configuration none
_chemical_formula_moiety         'C23 H32 O8, 2(C H Cl3)'
_chemical_formula_sum            'C25 H34 Cl6 O8'
_chemical_formula_weight         675.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3919(5)
_cell_length_b                   12.9423(6)
_cell_length_c                   21.1734(12)
_cell_measurement_reflns_used    3005
_cell_measurement_temperature    280(2)
_cell_measurement_theta_max      70.5120
_cell_measurement_theta_min      3.8490
_cell_volume                     3121.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      280(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0609844000
_diffrn_orient_matrix_UB_12      -0.0223429000
_diffrn_orient_matrix_UB_13      0.0634319000
_diffrn_orient_matrix_UB_21      -0.0622905000
_diffrn_orient_matrix_UB_22      -0.0939256000
_diffrn_orient_matrix_UB_23      -0.0296584000
_diffrn_orient_matrix_UB_31      0.1034262000
_diffrn_orient_matrix_UB_32      -0.0696984000
_diffrn_orient_matrix_UB_33      0.0196133000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10501
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.806
_diffrn_reflns_theta_min         4.003
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.400
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.005(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         5345
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0993P)^2^+0.5231P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1654
_reflns_Friedel_coverage         0.592
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.757
_reflns_number_gt                4720
_reflns_number_total             5345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00096_si_003.cif
_cod_data_source_block           chenjj_0113
_cod_original_cell_volume        3121.7(3)
_cod_database_code               1563902
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 93.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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. Uiso/Uaniso restraints and constraints
Uanis(Cl5) \\sim Ueq, Uanis(Cl5') \\sim Ueq, Uanis(Cl6) \\sim Ueq, Uanis(Cl6')
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H25(0.5) H25A(0.5) Cl5(0.5) Cl6(0.5) Cl5'(0.5) Cl6'(0.5)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C9(H9), C11(H11), C14(H14), C25(H25),
 C25(H25A), C24(H24)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C15(H15A,H15B)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
4.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              36600
_shelx_hkl_checksum              87506