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_7217672
_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         'C22 H36 O5'
_chemical_formula_sum            'C22 H36 O5'
_chemical_formula_weight         380.51
_chemical_melting_point          475.7
_chemical_name_common            'crotonlaevin G'
_chemical_name_systematic
;
 ?
;
_chemical_optical_rotation       '[\a]^26^~D~=+4.69 (c 0.64, in CHCl3)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   constr
_atom_sites_solution_primary     direct
_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                 112.7227(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3298(3)
_cell_length_b                   9.17075(12)
_cell_length_c                   24.6190(4)
_cell_measurement_reflns_used    11542
_cell_measurement_temperature    294.4(2)
_cell_measurement_theta_max      72.5003
_cell_measurement_theta_min      3.5871
_cell_volume                     4233.71(12)
_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)'
_diffrn_ambient_temperature      294.4(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -28.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   30.0000 38

  2 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 48

  3 omega   18.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   30.0000 45

  4 omega  -23.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 29

  5 omega -118.00  -79.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000 -120.0000 39

  6 omega  -43.00  -11.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   38.0000  120.0000 32

  7 omega -132.00 -107.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000   90.0000 25

  8 omega -100.00  -74.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000  120.0000 26

  9 omega   43.00  135.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       58.0000 -160.0000 -171.0000 92

 10 omega   27.00  122.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -90.0000 95

 11 omega -102.00  -60.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  178.0000  -60.0000 42

 12 omega   43.00   68.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -180.0000 25

 13 omega   41.00   80.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000    0.0000 39

 14 omega   41.00   75.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -90.0000 34

 15 omega  143.00  177.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -120.0000 34

 16 omega   41.00   93.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  120.0000 52

 17 omega  100.00  126.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -120.0000 26

 18 omega   42.00  109.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -94.0000  -63.6629 67

 19 omega   66.00   92.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000  -30.0000 26

 20 omega   51.00   76.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -180.0000 25

 21 omega   89.00  115.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   90.0000 26

 22 omega   95.00  178.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000   60.0000 83

 23 omega  127.00  153.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -11.0000  132.0000 26

 24 omega   73.00  115.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  160.0000   38.0000 42

 25 omega  138.00  164.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  160.0000   38.0000 26

 26 omega   92.00  161.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000   30.0000 69

 27 omega   47.00   85.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000   30.0000 38

 28 omega   46.00  111.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000   30.0000 65

 29 omega   54.00   85.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   30.0000 31

 30 omega   82.00  115.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -60.0000 33

 31 omega   46.00   91.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -90.0000 45

 32 omega  123.00  154.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000   90.0000 31

 33 omega   89.00  148.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000   60.0000 59

 34 omega  108.00  134.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000    0.0000 26

 35 omega   63.00   88.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   60.0000 25

 36 omega  122.00  148.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   90.0000 26

 37 omega   63.00   88.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -118.0000  113.0000 25

 38 omega   49.00   75.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -150.0000 26

 39 omega   78.00  114.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -150.0000 36

 40 omega   70.00   95.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   60.0000 25

 41 omega   87.00  112.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  120.0000 25

 42 omega  116.00  141.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -90.0000 25

 43 omega   89.00  114.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -106.0000 -178.8480 25

 44 omega   48.00   80.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  -90.0000 32

 45 omega   97.00  123.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  -90.0000 26

 46 omega   47.00   74.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -106.0000 -178.8480 27

 47 omega  -34.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   97.0000  164.0000 27

 48 omega   43.00   68.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -120.0000 25

 49 omega   43.00   77.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  120.0000 34

 50 omega  110.00  136.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   12.0000   90.0000 26

 51 omega -106.00  -80.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000 -180.0000 26

 52 omega -120.00  -79.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000   30.0000 41

 53 omega -101.00  -75.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000 -150.0000 26

 54 omega   92.00  151.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000   90.0000 59

 55 omega   74.00  125.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -30.0000 51

 56 omega   60.00   86.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  120.0000 26

 57 omega   56.00   96.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000   60.0000 40

 58 omega   65.00   97.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  120.0000 32

 59 omega   91.00  117.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   90.0000 26

 60 omega   72.00   98.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000 -150.0000 26

 61 omega  101.00  127.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000 -150.0000 26

 62 omega   61.00  104.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000 -120.0000 43

 63 omega  -31.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -120.0000 104

 64 omega  -71.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 95

 65 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 48

 66 omega  -71.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 95

 67 omega -130.00  -25.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  150.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0266159000
_diffrn_orient_matrix_UB_12      0.1527482000
_diffrn_orient_matrix_UB_13      0.0078850000
_diffrn_orient_matrix_UB_21      0.0724336000
_diffrn_orient_matrix_UB_22      0.0656336000
_diffrn_orient_matrix_UB_23      0.0064920000
_diffrn_orient_matrix_UB_31      -0.0282641000
_diffrn_orient_matrix_UB_32      0.0242705000
_diffrn_orient_matrix_UB_33      -0.0670481000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20139
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.076
_diffrn_reflns_theta_min         3.590
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71920
_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_density_diffrn    1.194
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 3043 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   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         7487
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0743P)^2^+0.9847P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.858
_reflns_Friedel_fraction_max     0.855
_reflns_number_gt                7275
_reflns_number_total             7487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra04863f2.cif
_cod_data_source_block           compound_7
_cod_original_cell_volume        4233.70(12)
_cod_database_code               7217672
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 96.63
_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,H) groups
2. Restrained distances
 H2BA-O2B
 0.86 with sigma of 0.02
 H2BB-O2B
 0.86 with sigma of 0.02
 H12B-H2BA
 2.2 with sigma of 0.02
 H12-H2B
 2.2 with sigma of 0.03
3. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H5A(0.5) H5B(0.5) H2BA(0.5) H2BB(0.5) H5BB(0.5)
 H5BC(0.5)
4.a Riding coordinates:
 O2(H2A,H2B), O5(H5A,H5B), O5B(H5BB,H5BC)
4.b Ternary CH refined with riding coordinates:
 C5(H5), C9(H9), C12(H12), C5B(H5BA), C9B(H9B), C12B(H12B)
4.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2C,H2D), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,
 H11B), C17(H17A,H17B), C18(H18A,H18B), C1B(H1BA,H1BB), C2B(H2BC,H2BD),
 C3B(H3BA,H3BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB), C11B(H11C,H11D), C17B(H17C,
 H17D), C18B(H18C,H18D)
4.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C14B(H14B)
4.e X=CH2 refined with riding coordinates:
 C15(H15A,H15B), C15B(H15C,H15D)
4.f Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C16B(H16D,H16E,H16F), C19B(H19D,H19E,H19F), C20B(H20D,H20E,H20F),
 C22B(H22D,H22E,H22F)
;
_shelx_res_checksum              83503
_olex2_submission_special_instructions 'No special instructions were received'