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_7217675
_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 O3'
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_chemical_melting_point          398
_chemical_name_common            'crotonlaevin N'
_chemical_optical_rotation       '[\a]^23^~D~=-18.75 (c 0.32, in CHCl3)'
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-09-25
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1319(6)
_cell_length_b                   14.3359(11)
_cell_length_c                   17.4859(15)
_cell_measurement_reflns_used    2258
_cell_measurement_temperature    291.4(1)
_cell_measurement_theta_max      72.5354
_cell_measurement_theta_min      3.9842
_cell_volume                     1787.8(3)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      291.44(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9731
_diffrn_measured_fraction_theta_max 0.9811
_diffrn_measurement_details
;
  1 omega  -30.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  116.0000  158.0000 28

  2 omega  -73.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 26

  3 omega  -79.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 43

  4 omega -126.00 -101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000  120.0000 25

  5 omega -132.00  -97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000 -120.0000 35

  6 omega -129.00  -99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000 -180.0000 30

  7 omega  -43.00    5.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   50.0000 -150.0000 48

  8 omega -115.00  -89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -91.0000   30.0000 26

  9 omega -132.00  -87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -91.0000  -60.0000 45

 10 omega   54.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -120.0000 33

 11 omega  109.00  145.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -60.0000 36

 12 omega   65.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -60.0000 27

 13 omega   41.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -30.0000 53

 14 omega   44.00   74.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   30.0000 30

 15 omega   45.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -120.0000 38

 16 omega   88.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -90.0000 26

 17 omega   67.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   60.0000 26

 18 omega  138.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 38

 19 omega   94.00  119.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 25

 20 omega  146.00  172.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   12.0000    0.0000 26

 21 omega  107.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000    0.0000 26

 22 omega  148.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000    0.0000 30

 23 omega  102.00  128.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   12.0000    0.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1552537000
_diffrn_orient_matrix_UB_12      0.0601983000
_diffrn_orient_matrix_UB_13      -0.0362686000
_diffrn_orient_matrix_UB_21      0.0916529000
_diffrn_orient_matrix_UB_22      -0.0124182000
_diffrn_orient_matrix_UB_23      -0.0791319000
_diffrn_orient_matrix_UB_31      -0.1190502000
_diffrn_orient_matrix_UB_32      -0.0881069000
_diffrn_orient_matrix_UB_33      -0.0136956000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4991
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         3.99
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95352
_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_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.1181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2703
_reflns_number_total             2976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra04863f2.cif
_cod_data_source_block           compound_15
_cod_database_code               7217675
_reflns_odcompleteness_completeness 97.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33