Dongtingnoids A-G: Fusicoccane Diterpenoids from a Penicillium Species.
Bie, Qiong; Chen, Chunmei; Yu, Muyuan; Guo, Jieru; Wang, Jianping; Liu, Junjun; Zhou, Yuan; Zhu, Hucheng; Zhang, Yonghui; Journal of natural products 82 (2019) 80–86; doi:10.1021/acs.jnatprod.8b00694

data_1552601
_publ_section_title
;
 Dongtingnoids A-G: Fusicoccane Diterpenoids from a Penicillium Species.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              80
_journal_page_last               86
_journal_paper_doi               10.1021/acs.jnatprod.8b00694
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H30 O4, 0.5(H2 O)'
_chemical_formula_sum            'C20 H31 O4.5'
_chemical_formula_weight         343.44
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.3149(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.22937(4)
_cell_length_b                   28.66155(14)
_cell_length_c                   9.57923(7)
_cell_measurement_reflns_used    33677
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6450
_cell_measurement_theta_min      4.6150
_cell_volume                     1849.09(2)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -88.00 -36.00   0.50    0.50    --    0.00 -19.00 120.00  104
  2  \w    -13.00  78.00   0.50    0.50    --    0.00  19.00  90.00  182
  3  \w    -16.00  88.00   0.50    0.50    --    0.00  38.00-180.00  208
  4  \w     12.00  70.00   0.50    0.50    --    0.00  38.00 -30.00  116
  5  \w    -23.00  16.00   0.50    0.50    --    0.00 -19.00 120.00   78
  6  \w    -20.00  22.00   0.50    0.50    --    0.00 -57.00 -60.00   84
  7  \w    -83.00 -25.00   0.50    0.50    --    0.00 -57.00 -60.00  116
  8  \w    -21.00  28.00   0.50    0.50    --    0.00 -77.00 -30.00   98
  9  \w    -45.00  29.00   0.50    0.50    --    0.00 -77.00  30.00  148
 10  \w     69.00 127.00   0.50    1.50    --   94.60  66.00   8.51  116
 11  \w     68.00  93.00   0.50    1.50    --   94.60  70.00 153.65   50
 12  \w     72.00  98.00   0.50    1.50    --   94.60  56.00 -47.31   52
 13  \w     69.00  95.00   0.50    1.50    --   94.60  70.00-117.04   52
 14  \w     66.00  91.00   0.50    1.50    --   94.60  74.00  24.31   50
 15  \w     67.00  92.00   0.50    1.50    --   94.60  72.00  93.49   50
 16  \w     72.00 156.00   0.50    1.50    --   94.60  55.00 -59.40  168
 17  \w    123.00 177.00   0.50    1.50    --   94.60  72.00 168.89  108
 18  \w     68.00  94.00   0.50    1.50    --   94.60  70.00 -49.03   52
 19  \w     69.00  95.00   0.50    1.50    --   94.60  69.00 -92.91   52
 20  \w     67.00  99.00   0.50    1.50    --   94.60  72.00 168.89   64
 21  \w      6.00 118.00   0.50    1.50    --   94.60 -61.00 120.00  224
 22  \w     71.00 106.00   0.50    1.50    --   94.60  61.00-150.00   70
 23  \w     27.00  53.00   0.50    1.50    --   94.60 -82.00 -60.00   52
 24  \w     91.00 117.00   0.50    1.50    --   94.60 -82.00 -60.00   52
 25  \w      5.00 126.00   0.50    1.50    --   94.60 -82.00 120.00  242
 26  \w     68.00  94.00   0.50    1.50    --   94.60  69.00-143.62   52
 27  \w      5.00 116.00   0.50    1.50    --   94.60 -82.00   0.00  222
 28  \w      7.00  77.00   0.50    1.50    --   94.60 -77.00-120.00  140
 29  \w     90.00 124.00   0.50    1.50    --   94.60 -77.00-120.00   68
 30  \w    119.00 183.00   0.50    1.50    --   94.60  74.00 105.92  128
 31  \w     66.00  91.00   0.50    1.50    --   94.60  74.00 105.92   50
 32  \w     70.00  95.00   0.50    1.50    --   94.60  66.00 135.00   50
 33  \w     71.00  98.00   0.50    1.50    --   94.60  61.00  90.00   54
 34  \w     71.00 183.00   0.50    1.50    --   94.60  62.00  77.17  224
 35  \w     45.00 117.00   0.50    1.50    --   94.60 -61.00   0.00  144
 36  \w     67.00  93.00   0.50    1.50    --   94.60  71.00  16.11   52
 37  \w     71.00 110.00   0.50    1.50    --   94.60  61.00  60.00   78
 38  \w     71.00  97.00   0.50    1.50    --   94.60  61.00   0.00   52
 39  \w     45.00 115.00   0.50    1.50    --   94.60 -82.00-150.00  140
 40  \w     70.00 174.00   0.50    1.50    --   94.60  63.00-142.17  208
 41  \w     71.00 147.00   0.50    1.50    --   94.60  61.00-120.00  152
 42  \w     71.00 103.00   0.50    1.50    --   94.60  61.00 -90.00   64
 43  \w     71.00  97.00   0.50    1.50    --   94.60  61.00 -60.00   52
 44  \w     69.00 106.00   0.50    1.50    --   94.60  67.00  94.46   74
 45  \w     70.00  95.00   0.50    1.50    --   94.60  65.00 -21.33   50
 46  \w     70.00 181.00   0.50    1.50    --   94.60  63.00 -41.55  222
 47  \w     71.00 162.00   0.50    1.50    --   94.60  61.00 150.00  182
 48  \w     67.00  97.00   0.50    1.50    --   94.60  72.00 179.52   60
 49  \w     75.00 176.00   0.50    1.50    --   94.60  45.00  60.00  202
 50  \w     70.00 122.00   0.50    1.50    --   94.60  64.00 129.11  104
 51  \w     72.00 171.00   0.50    1.50    --   94.60  58.00 -18.68  198
;
_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      0.0525353000
_diffrn_orient_matrix_UB_12      0.0516867000
_diffrn_orient_matrix_UB_13      0.0383936000
_diffrn_orient_matrix_UB_21      -0.2226356000
_diffrn_orient_matrix_UB_22      0.0121021000
_diffrn_orient_matrix_UB_23      -0.0534638000
_diffrn_orient_matrix_UB_31      0.0028519000
_diffrn_orient_matrix_UB_32      -0.0083488000
_diffrn_orient_matrix_UB_33      0.1596484000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            40459
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.991
_diffrn_reflns_theta_min         3.084
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57222
_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_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 3458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         7310
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0244
_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^)+(0.0361P)^2^+0.2955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0637
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                7256
_reflns_number_total             7310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00694_si_003.cif
_cod_data_source_block           20180523_bq1_18_2
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C20 H30 O4), H2 O'
_cod_original_formula_sum        'C40 H62 O9'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     686.89
_cod_database_code               1552601
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.724
_reflns_odcompleteness_completeness 99.94
_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
2.a Ternary CH refined with riding coordinates:
 C00E(H00R), C00H(H00H), C00I(H00I), C00K(H00K), C00R(H00X), C00X(H00Z),
 C013(H013), C017(H017)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B), C00Q(H00V,H00W), C00S(H00F,H00G), C00V(H00Y,H), C00W(H00J,
 H00L), C00Y(H00M,H00N), C010(H01A,H01B), C011(H01J,H01K), C015(H01O,H01P),
 C016(H01C,H01D), C018(H01Q,H01R), C019(H01S,H01T), C01B(H01U,H01V), C01C(H01H,
 H01I)
2.c Idealised Me refined as rotating group:
 C00O(H00C,H00D,H00E), C00P(H00S,H00T,H00U), C00Z(H00O,H00P,H00Q), C014(H01L,
 H01M,H01N), C01A(H01E,H01F,H01G), C01D(H01W,H01X,H01Y)
;
_shelx_res_checksum              41189
_shelx_hkl_checksum              51631
_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 1.507
_oxdiff_exptl_absorpt_empirical_full_min 0.650