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_7156546
_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         'C19 H28 O2'
_chemical_formula_sum            'C19 H28 O2'
_chemical_formula_weight         288.41
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2018-09-20 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.08920(10)
_cell_length_b                   9.97190(10)
_cell_length_c                   17.83610(10)
_cell_measurement_reflns_used    24515
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6470
_cell_measurement_theta_min      4.9500
_cell_volume                     1616.60(3)
_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 0.999
_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    -29.00  29.00   0.50    0.50    --    0.00 -77.00-150.00  116
  2  \w     32.00  67.00   0.50    0.50    --    0.00  38.00-120.00   70
  3  \w     44.00  85.00   0.50    0.50    --    0.00  57.00-180.00   82
  4  \w    -40.00  -8.00   0.50    0.50    --    0.00 -77.00 -60.00   64
  5  \w     -4.00  29.00   0.50    0.50    --    0.00  57.00-180.00   66
  6  \w     35.00  72.00   0.50    0.50    --    0.00  38.00-180.00   74
  7  \w     -9.00  16.00   0.50    0.50    --    0.00  38.00-120.00   50
  8  \w     46.00  74.00   0.50    0.50    --    0.00  38.00 120.00   56
  9  \w    -16.00   9.00   0.50    0.50    --    0.00  38.00-180.00   50
 10  \w    -17.00  61.00   0.50    0.50    --    0.00  19.00  60.00  156
 11  \w    -16.00  88.00   0.50    0.50    --    0.00  38.00 -60.00  208
 12  \w    -15.00  22.00   0.50    0.50    --    0.00  38.00 120.00   74
 13  \w     71.00  96.00   0.50    0.70    --   94.60  60.00  82.96   50
 14  \w     74.00 184.00   0.50    0.70    --   94.60  51.00  59.07  220
 15  \w     75.00 111.00   0.50    0.70    --   94.60  45.00 162.75   72
 16  \w     68.00  93.00   0.50    0.70    --   94.60  69.00 157.66   50
 17  \w    127.00 166.00   0.50    0.70    --   94.60  75.00 -38.55   78
 18  \w    159.00 184.00   0.50    0.70    --   94.60  67.00-132.73   50
 19  \w     69.00  97.00   0.50    0.70    --   94.60  66.00 165.01   56
 20  \w     68.00  93.00   0.50    0.70    --   94.60  69.00  27.18   50
 21  \w    146.00 172.00   0.50    0.70    --   94.60  73.00 174.60   52
 22  \w     66.00  94.00   0.50    0.70    --   94.60  75.00 -38.55   56
 23  \w    106.00 132.00   0.50    0.70    --   94.60  69.00  27.18   52
 24  \w     67.00  92.00   0.50    0.70    --   94.60  72.00  15.64   50
 25  \w     73.00 103.00   0.50    0.70    --   94.60  52.00   7.07   60
 26  \w     67.00  93.00   0.50    0.70    --   94.60  73.00 -11.26   52
 27  \w     66.00  91.00   0.50    0.70    --   94.60  75.00-161.57   50
 28  \w     75.00 133.00   0.50    0.70    --   94.60  47.00 -20.79  116
 29  \w     68.00 117.00   0.50    0.70    --   94.60  69.00-107.07   98
 30  \w     10.00  64.00   0.50    0.70    --   94.60 -82.00-150.00  108
 31  \w     67.00  94.00   0.50    0.70    --   94.60  73.00 174.60   54
 32  \w    107.00 184.00   0.50    0.70    --   94.60  67.00 101.07  154
 33  \w    111.00 146.00   0.50    0.70    --   94.60  67.00 119.81   70
 34  \w     69.00  94.00   0.50    0.70    --   94.60  67.00-132.73   50
 35  \w     71.00 135.00   0.50    0.70    --   94.60  61.00 -60.00  128
 36  \w      7.00 126.00   0.50    0.70    --   94.60 -82.00   0.00  238
 37  \w     70.00 103.00   0.50    0.70    --   94.60  67.00 101.07   66
 38  \w      6.00 121.00   0.50    0.70    --   94.60 -82.00-180.00  230
 39  \w     70.00  97.00   0.50    0.70    --   94.60  64.00  97.25   54
 40  \w     69.00  99.00   0.50    0.70    --   94.60  67.00 119.81   60
 41  \w     71.00  96.00   0.50    0.70    --   94.60  61.00 150.00   50
 42  \w    116.00 182.00   0.50    0.70    --   94.60  61.00 150.00  132
 43  \w     69.00 121.00   0.50    0.70    --   94.60  68.00-123.15  104
 44  \w     76.00 113.00   0.50    0.70    --   94.60  45.00  90.00   74
 45  \w      7.00  32.00   0.50    0.70    --   94.60 -77.00  30.00   50
 46  \w     40.00  77.00   0.50    0.70    --   94.60 -77.00  30.00   74
 47  \w     92.00 124.00   0.50    0.70    --   94.60 -77.00  30.00   64
 48  \w     71.00 105.00   0.50    0.70    --   94.60  61.00-150.00   68
 49  \w     71.00  97.00   0.50    0.70    --   94.60  61.00  90.00   52
 50  \w     67.00 110.00   0.50    0.70    --   94.60  71.00 -94.30   86
 51  \w    148.00 178.00   0.50    0.70    --   94.60  71.00 -94.30   60
 52  \w     72.00  98.00   0.50    0.70    --   94.60  61.00 -30.00   52
 53  \w     72.00 160.00   0.50    0.70    --   94.60  61.00-180.00  176
 54  \w     90.00 126.00   0.50    0.70    --   94.60 -82.00  90.00   72
 55  \w     74.00 184.00   0.50    0.70    --   94.60  50.00  28.20  220
 56  \w     71.00  97.00   0.50    0.70    --   94.60  61.00  60.00   52
 57  \w      5.00  83.00   0.50    0.70    --   94.60 -82.00  90.00  156
 58  \w     97.00 122.00   0.50    0.70    --   94.60 -82.00-150.00   50
 59  \w     13.00 126.00   0.50    0.70    --   94.60 -82.00 -90.00  226
 60  \w    152.00 177.00   0.50    0.70    --   94.60  60.00  82.96   50
 61  \w     72.00 177.00   0.50    0.70    --   94.60  55.00-131.77  210
 62  \w     67.00  93.00   0.50    0.70    --   94.60 -82.00-150.00   52
 63  \w    107.00 132.00   0.50    0.70    --   94.60  66.00 165.01   50
 64  \w    105.00 174.00   0.50    0.70    --   94.60  74.00 -88.09  138
 65  \w     66.00  91.00   0.50    0.70    --   94.60  74.00 -88.09   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      -0.0053726000
_diffrn_orient_matrix_UB_12      0.0618026000
_diffrn_orient_matrix_UB_13      0.0791352000
_diffrn_orient_matrix_UB_21      0.1568627000
_diffrn_orient_matrix_UB_22      0.0552552000
_diffrn_orient_matrix_UB_23      -0.0106617000
_diffrn_orient_matrix_UB_31      -0.0639147000
_diffrn_orient_matrix_UB_32      0.1304108000
_diffrn_orient_matrix_UB_33      -0.0329031000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36958
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.898
_diffrn_reflns_theta_min         4.959
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49498
_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    1.185
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1339 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0391P)^2^+0.4420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3209
_reflns_number_total             3263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02353k2.cif
_cod_data_source_block           20180905_lfl_3-20-4
_cod_depositor_comments
'Adding full bibliography for 7156543--7156546.cif.'
_cod_database_code               7156546
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.802
_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:
 C7(H7), C8(H8), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,
 H13B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 2.179
_oxdiff_exptl_absorpt_empirical_full_min 0.528