ent-Strobane and ent-Pimarane Diterpenoids from Siegesbeckia pubescens.
Wang, Jianbin; Duan, Hongquan; Wang, Yi; Pan, Bowen; Gao, Chun; Gai, Chunyan; Wu, Qiong; Fu, Hongzheng; Journal of natural products 80 (2017) 19–29; doi:10.1021/acs.jnatprod.6b00150

data_1544925
_publ_section_title
;
 ent-Strobane and ent-Pimarane Diterpenoids from Siegesbeckia pubescens.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              19
_journal_page_last               29
_journal_paper_doi               10.1021/acs.jnatprod.6b00150
_journal_volume                  80
_journal_year                    2017
_chemical_formula_moiety         'C20 H34 O4'
_chemical_formula_sum            'C20 H34 O4'
_chemical_formula_weight         338.47
_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     dual
_audit_creation_date             2015-02-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.622(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.342(4)
_cell_length_b                   15.348(12)
_cell_length_c                   8.002(4)
_cell_measurement_reflns_used    1345
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      21.5
_cell_volume                     891.5(10)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      93
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
    Number of images: 150
               Slice: -90.0000 - 60.0000
         Image width: 1.0000
            Exp time: 1.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 120.0000
                 XTD: 39.8280
              2theta: 0.3363
scan:
    Number of images: 165
               Slice: -90.0000 - 75.0000
         Image width: 1.0000
            Exp time: 1.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 60.0000
                 XTD: 39.8280
              2theta: 0.3363
scan:
    Number of images: 162
               Slice: -90.0000 - 72.0000
         Image width: 1.0000
            Exp time: 1.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 240.0000
                 XTD: 39.8280
              2theta: 0.3363
scan:
    Number of images: 140
               Slice: -55.0000 - 85.0000
         Image width: 1.0000
            Exp time: 1.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 0.0000
                 XTD: 39.8280
              2theta: 0.3363
scan:
    Number of images: 180
               Slice: -135.0000 - 45.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 240.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 180
               Slice: -135.0000 - 45.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 180.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 180
               Slice: -135.0000 - 45.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 60.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 180
               Slice: -135.0000 - 45.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 240.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 180
               Slice: -135.0000 - 45.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 180.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 162
               Slice: -135.0000 - 27.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 60.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 159
               Slice: -135.0000 - 24.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 300.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 150
               Slice: -135.0000 - 15.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 0.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 150
               Slice: -135.0000 - 15.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 240.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 156
               Slice: -135.0000 - 21.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 120.0000
                 XTD: 39.8280
              2theta: -44.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 60.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 300.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 300.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 60.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 0.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 0.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 179
               Slice: -180.0000 - -1.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 240.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 240.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 164
               Slice: -180.0000 - -16.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 240.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 120.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 180
               Slice: -180.0000 - 0.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 120.0000
                 XTD: 39.8280
              2theta: -89.6637
scan:
    Number of images: 160
               Slice: -180.0000 - -20.0000
         Image width: 1.0000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 60.0000
                 Phi: 180.0000
                 XTD: 39.8280
              2theta: -89.6637
;
_diffrn_measurement_device
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn944+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.075564
_diffrn_orient_matrix_UB_12      0.045186
_diffrn_orient_matrix_UB_13      -0.105945
_diffrn_orient_matrix_UB_21      0.049054
_diffrn_orient_matrix_UB_22      -0.013448
_diffrn_orient_matrix_UB_23      -0.040723
_diffrn_orient_matrix_UB_31      -0.055855
_diffrn_orient_matrix_UB_32      -0.108993
_diffrn_orient_matrix_UB_33      -0.031289
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27802
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_min         5.592
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   DTABSCOR
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       Prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1429 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(18)
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0883P)^2^+0.4819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1497
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3096
_reflns_number_total             3239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00150_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1544924--1544925.cif.'
_cod_database_code               1544925
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.876
_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:
 C2(H2A), C9(H9), C5(H5), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C3(H3A,H3B), C1(H1A,H1B), C19(H19A,H19B), C16(H16A,
 H16B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O3(H3), O1(H1)
;
_shelx_res_checksum              54666
_shelx_hkl_checksum              6989
_olex2_submission_special_instructions 'No special instructions were received'