Labdane-Type Diterpenoids from Croton laevigatus
Huang, Hong-Li; Qi, Feng-Ming; Yuan, Ji-Cheng; Zhao, Cai-Gui; Yang, Jing-Wei; Fang, Fu-Hu; Wu, Quan-xiang; Gao, Kun; Yuan, Cheng-Shan; RSC Advances  (2014) –; doi:10.1039/C4RA04863F

data_7217674
_publ_section_title
;
 Labdane-Type Diterpenoids from Croton laevigatus
;
_journal_name_full               'RSC Advances'
_journal_paper_doi               10.1039/C4RA04863F
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H30 O4'
_chemical_formula_sum            'C20 H30 O4'
_chemical_formula_weight         334.44
_chemical_name_common            'crotonlaevin M'
_chemical_optical_rotation       '[\a]^26^~D~=+10.0 (c 0.10, in CHCl3)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.829(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1613(4)
_cell_length_b                   11.8102(7)
_cell_length_c                   16.9960(9)
_cell_measurement_reflns_used    8009
_cell_measurement_temperature    290(1)
_cell_measurement_theta_max      72.6904
_cell_measurement_theta_min      6.1284
_cell_volume                     1829.40(17)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      290(1)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -71.00  -43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000 -150.0000 28

  2 omega  -77.00  -39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 38

  3 omega  -61.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000 -120.0000 33

  4 omega  -12.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000 -120.0000 42

  5 omega  -81.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 29

  6 omega  -80.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 45

  7 omega  -91.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  125.0000 -120.0000 79

  8 omega -131.00  -79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000  -30.0000 52

  9 omega -130.00  -79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000  120.0000 51

 10 omega  -67.00  -41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000 -120.0000 26

 11 omega -117.00  -80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000   60.0000 37

 12 omega  -64.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000 -150.0000 30

 13 omega -130.00 -104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -101.0000   43.0000 26

 14 omega -125.00  -99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000 -120.0000 26

 15 omega   26.00   51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -180.0000 25

 16 omega -129.00  -33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -180.0000 96

 17 omega  -58.00  -32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -120.0000 26

 18 omega  -49.00    9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   38.0000   90.0000 58

 19 omega -126.00  -86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -63.0000  -90.0000 40

 20 omega -124.00  -32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -150.0000 92

 21 omega  -70.00  -40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -63.0000  -90.0000 30

 22 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  150.0000 26

 23 omega   71.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -101.0000   31.0000 26

 24 omega  100.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000    0.0000 49

 25 omega   83.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -180.0000 48

 26 omega   87.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -120.0000 48

 27 omega  117.00  155.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -180.0000 38

 28 omega  131.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  120.0000 38

 29 omega   61.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -120.0000 41

 30 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -150.0000 25

 31 omega   91.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -180.0000 27

 32 omega  122.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -60.0000 27

 33 omega   67.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000 -180.0000 46

 34 omega  133.00  159.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  -60.0000 26

 35 omega  152.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   30.0000 26

 36 omega  115.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   76.0000 -135.0670 62

 37 omega   86.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  -60.0000 36

 38 omega   51.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -180.0000 37

 39 omega  100.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   30.0000 25

 40 omega  123.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000 -180.0000 26

 41 omega   44.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000 -180.0000 63

 42 omega  138.00  164.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -120.0000 26

 43 omega  106.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  -30.0000 70

 44 omega  144.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -150.0000 26

 45 omega   90.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  -90.0000 36

 46 omega   85.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -180.0000 41

 47 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -120.0000 26

 48 omega  125.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000  -90.0000 40

 49 omega   61.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000 -120.0000 32

 50 omega   45.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -60.0000 48

 51 omega   83.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   76.0000  -81.6663 69

 52 omega   90.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -150.0000 27

 53 omega  139.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 26

 54 omega   96.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 34

 55 omega   48.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000 -180.0000 46

 56 omega   43.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -60.0000 49

 57 omega   52.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  120.0000 27

 58 omega   92.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  -90.0000 25

 59 omega   47.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -150.0000 29

 60 omega   44.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -120.0000 37

 61 omega   93.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -180.0000 85

 62 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  -90.0000 25

 63 omega  104.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  150.0000 26

 64 omega   64.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000 -180.0000 26

 65 omega   89.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   65.0000  174.4279 31

 66 omega   92.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -120.0000 25

 67 omega   93.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -120.0000 31

 68 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   76.0000 -135.0670 25

 69 omega   88.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000 -120.0000 26

 70 omega   80.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   33.0000 -116.8183 30

 71 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 48

 72 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 48

 73 omega  -73.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000   60.0000 104

 74 omega  -72.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000    0.0000 105

 75 omega -130.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000    0.0000 105

 76 omega  -74.00   13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   57.0000 -150.0000 87

 77 omega -130.00  -73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000 -180.0000 57

 78 omega -130.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000   60.0000 105

 79 omega -131.00  -27.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -38.0000   60.0000 104

 80 omega -130.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  -60.0000 105

 81 omega    4.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000 -101.0000   31.0000 100

 82 omega   25.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  150.0000 105

 83 omega -137.00  -31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000  120.0000 106

 84 omega   42.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   30.0000 74

 85 omega   72.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000    0.0000 106

 86 omega   43.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -30.0000 50

 87 omega   44.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000   60.0000 60

 88 omega   83.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   30.0000 95

 89 omega   42.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -101.0000 -136.0000 70

 90 omega   41.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000   90.0000 53

 91 omega   80.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   33.0000  137.0506 98

 92 omega   77.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   29.0000   35.0000 101

 93 omega   42.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   90.0000 74

 94 omega   42.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -30.0000 74

 95 omega   87.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   69.0000   18.3623 91

 96 omega   82.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   35.0000   94.4299 96
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1627586000
_diffrn_orient_matrix_UB_12      0.0351445000
_diffrn_orient_matrix_UB_13      -0.0079062000
_diffrn_orient_matrix_UB_21      0.0121076000
_diffrn_orient_matrix_UB_22      0.0376982000
_diffrn_orient_matrix_UB_23      -0.0857702000
_diffrn_orient_matrix_UB_31      -0.0436607000
_diffrn_orient_matrix_UB_32      -0.1198725000
_diffrn_orient_matrix_UB_33      -0.0297805000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17362
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.844
_diffrn_reflns_theta_min         6.133
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0613P)^2^+0.3229P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                3475
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra04863f2.cif
_cod_data_source_block           compound_14
_cod_database_code               7217674
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 97.16
_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. Restrained distances
 H4-O4
 0.82 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4A), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              11629
_olex2_submission_special_instructions 'No special instructions were received'