Anti-inflammatory fusicoccane-type diterpenoids from the phytopathogenic fungus Alternaria brassicicola.
Li, Fengli; Sun, Weiguang; Guan, Jiankun; Lu, Yuanyuan; Lin, Shuang; Zhang, Sitian; Gao, Weixi; Liu, Junjun; Du, Guang; Wang, Jianping; Zhu, Hucheng; Qi, Changxing; Hu, Zhengxi; Zhang, Yonghui; Organic & biomolecular chemistry 16 (2018) 8751–8760; doi:10.1039/c8ob02353k

data_7156545
_publ_section_title
;
 Anti-inflammatory fusicoccane-type diterpenoids from the phytopathogenic
 fungus Alternaria brassicicola.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8751
_journal_page_last               8760
_journal_paper_doi               10.1039/c8ob02353k
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C22 H36 O4'
_chemical_formula_sum            'C22 H36 O4'
_chemical_formula_weight         364.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2018-09-21 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.6090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.856
_cell_length_b                   15.76930(10)
_cell_length_c                   9.69440(10)
_cell_measurement_reflns_used    20148
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6800
_cell_measurement_theta_min      4.6410
_cell_volume                     1026.663(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -18.00  41.00   0.50    0.50    --    0.00  41.00 112.00  118
  2  \w     48.00  87.00   0.50    0.50    --    0.00  41.00 112.00   78
  3  \w    159.00 184.00   0.50    0.50    --   94.60  41.00 112.00   50
  4  \w     38.00  64.00   0.50    0.50    --   94.60 -41.00 -40.00   52
  5  \w     28.00  54.00   0.50    0.50    --    0.00  38.00  60.00   52
  6  \w    -16.00  20.00   0.50    0.50    --    0.00  38.00  60.00   72
  7  \w    -12.00  13.00   0.50    0.50    --    0.00 -77.00  90.00   50
  8  \w    -89.00 -63.00   0.50    0.50    --    0.00 -41.00 -40.00   52
  9  \w    -46.00 -14.00   0.50    0.50    --    0.00 -77.00  90.00   64
 10  \w    -19.00  21.00   0.50    0.50    --    0.00 -57.00-120.00   80
 11  \w     49.00  86.00   0.50    0.50    --    0.00  38.00 -60.00   74
 12  \w    -17.00  86.00   0.50    0.50    --    0.00  38.00-180.00  206
 13  \w    -89.00 -40.00   0.50    0.50    --    0.00 -57.00-120.00   98
 14  \w    -23.00   3.00   0.50    0.50    --    0.00 -41.00 -40.00   52
 15  \w    -17.00  34.00   0.50    0.50    --    0.00  38.00 -60.00  102
 16  \w     -1.00  31.00   0.50    0.50    --    0.00 -82.00  60.00   64
 17  \w     71.00 106.00   0.50    0.50    --   94.60  61.00  30.00   70
 18  \w    141.00 176.00   0.50    0.50    --   94.60  53.00 176.43   70
 19  \w     11.00 126.00   0.50    0.50    --   94.60 -82.00 120.00  230
 20  \w     73.00 137.00   0.50    0.50    --   94.60  53.00 176.43  128
 21  \w    144.00 170.00   0.50    0.50    --   94.60  71.00-136.46   52
 22  \w    146.00 172.00   0.50    0.50    --   94.60  66.00  48.29   52
 23  \w     75.00 139.00   0.50    0.50    --   94.60  45.00 -90.00  128
 24  \w     72.00 102.00   0.50    0.50    --   94.60  57.00 -71.49   60
 25  \w    107.00 184.00   0.50    0.50    --   94.60  64.00 -53.90  154
 26  \w     67.00  95.00   0.50    0.50    --   94.60  71.00-136.46   56
 27  \w      5.00  70.00   0.50    0.50    --   94.60 -82.00   0.00  130
 28  \w     79.00 126.00   0.50    0.50    --   94.60 -82.00   0.00   94
 29  \w     72.00  98.00   0.50    0.50    --   94.60  56.00  80.08   52
 30  \w     72.00 118.00   0.50    0.50    --   94.60  60.00 -13.53   92
 31  \w    123.00 183.00   0.50    0.50    --   94.60  60.00 -13.53  120
 32  \w     74.00  99.00   0.50    0.50    --   94.60  61.00 -30.00   50
 33  \w     71.00 119.00   0.50    0.50    --   94.60  60.00 -68.47   96
 34  \w    139.00 173.00   0.50    0.50    --   94.60  60.00 -68.47   68
 35  \w     71.00  98.00   0.50    0.50    --   94.60  64.00 -53.90   54
 36  \w     72.00  98.00   0.50    0.50    --   94.60  61.00   0.00   52
 37  \w    132.00 158.00   0.50    0.50    --   94.60  71.00 178.94   52
 38  \w     69.00  94.00   0.50    0.50    --   94.60  66.00  48.29   50
 39  \w     78.00 147.00   0.50    0.50    --   94.60  45.00-120.00  138
 40  \w     75.00 184.00   0.50    0.50    --   94.60  45.00 120.00  218
 41  \w     76.00 178.00   0.50    0.50    --   94.60  45.00  60.00  204
 42  \w    132.00 172.00   0.50    0.50    --   94.60  67.00   0.15   80
 43  \w     75.00 111.00   0.50    0.50    --   94.60  45.00  90.00   72
 44  \w     74.00 111.00   0.50    0.50    --   94.60  50.00 -22.59   74
 45  \w     71.00  98.00   0.50    0.50    --   94.60  61.00-150.00   54
 46  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 -90.00   50
 47  \w     72.00  98.00   0.50    0.50    --   94.60  59.00  86.50   52
 48  \w     75.00 151.00   0.50    0.50    --   94.60  49.00-149.69  152
 49  \w     72.00  98.00   0.50    0.50    --   94.60  68.00-156.41   52
 50  \w     73.00 100.00   0.50    0.50    --   94.60  61.00 120.00   54
 51  \w     70.00  96.00   0.50    0.50    --   94.60  64.00 104.35   52
 52  \w     68.00  94.00   0.50    0.50    --   94.60  71.00 178.94   52
 53  \w     69.00 129.00   0.50    0.50    --   94.60  67.00   0.15  120
 54  \w     17.00  99.00   0.50    0.50    --   94.60 -61.00  60.00  164
 55  \w     69.00  94.00   0.50    0.50    --   94.60  67.00  83.01   50
 56  \w     72.00  98.00   0.50    0.50    --   94.60  61.00-180.00   52
 57  \w     67.00 124.00   0.50    0.50    --   94.60  71.00 122.76  114
 58  \w     45.00 126.00   0.50    0.50    --   94.60 -82.00-180.00  162
 59  \w      6.00 126.00   0.50    0.50    --   94.60 -82.00 -90.00  240
 60  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 150.00   50
 61  \w    117.00 142.00   0.50    0.50    --   94.60  61.00 150.00   50
 62  \w     34.00 125.00   0.50    0.50    --   94.60 -82.00 -60.00  182
 63  \w    143.00 168.00   0.50    0.50    --   94.60  45.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2029525000
_diffrn_orient_matrix_UB_12      0.0411135000
_diffrn_orient_matrix_UB_13      -0.0606104000
_diffrn_orient_matrix_UB_21      0.0790340000
_diffrn_orient_matrix_UB_22      0.0295003000
_diffrn_orient_matrix_UB_23      -0.1300398000
_diffrn_orient_matrix_UB_31      -0.0720114000
_diffrn_orient_matrix_UB_32      -0.0835705000
_diffrn_orient_matrix_UB_33      -0.0757208000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22706
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.900
_diffrn_reflns_theta_min         4.656
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.166
_refine_ls_abs_structure_details
;
 Flack x determined using 1916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0444P)^2^+0.1515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                4086
_reflns_number_total             4094
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02353k2.cif
_cod_data_source_block           20180917_lfl_2-16-3
_cod_depositor_comments
'Adding full bibliography for 7156543--7156546.cif.'
_cod_original_cell_volume        1026.588(13)
_cod_database_code               7156545
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.929
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6(H6), C7(H7), C8(H8), C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C13(H13A,H13B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.d 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)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2)
;
_shelx_shelxl_version_number     2014/7
_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 1.551
_oxdiff_exptl_absorpt_empirical_full_min 0.741