Cytotoxic Cleistanthane and Cassane Diterpenoids from the Entomogenous Fungus Paraconiothyrium hawaiiense.
Chen, Shenxi; Zhang, Yang; Niu, Shubin; Liu, Xingzhong; Che, Yongsheng; Journal of natural products 77 (2014) 1513–1518; doi:10.1021/np500302e

data_1516470
_publ_section_title
;
 Cytotoxic Cleistanthane and Cassane Diterpenoids from the Entomogenous
 Fungus Paraconiothyrium hawaiiense.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1513
_journal_page_last               1518
_journal_paper_doi               10.1021/np500302e
_journal_volume                  77
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H26 O4'
_chemical_formula_sum            'C20 H26 O4'
_chemical_formula_weight         330.41
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-14
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3028(3)
_cell_length_b                   13.9746(13)
_cell_length_c                   16.4665(12)
_cell_measurement_reflns_used    3328
_cell_measurement_temperature    99.8
_cell_measurement_theta_max      71.6183
_cell_measurement_theta_min      4.1425
_cell_volume                     1680.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      99.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega   -7.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   42.0000  -83.0000 51

  2 omega  -92.00  -46.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000 -150.0000 46

  3 omega  -49.00   30.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -90.0000 79

  4 omega   -5.00   50.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000  120.0000 55

  5 omega   -6.00   68.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000 -120.0000 74

  6 omega  150.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 25

  7 omega   55.00  162.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000   60.0000 107

  8 omega  111.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   90.0000 56

  9 omega  101.00  127.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 26

 10 omega  150.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 26

 11 omega   85.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 35

 12 omega  106.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -180.0000 67

 13 omega  119.00  174.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  120.0000 55

 14 omega   89.00  136.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1035056000
_diffrn_orient_matrix_UB_12      0.0378793000
_diffrn_orient_matrix_UB_13      -0.0747211000
_diffrn_orient_matrix_UB_21      -0.0377841000
_diffrn_orient_matrix_UB_22      0.1034759000
_diffrn_orient_matrix_UB_23      0.0274541000
_diffrn_orient_matrix_UB_31      0.1794903000
_diffrn_orient_matrix_UB_32      -0.0002097000
_diffrn_orient_matrix_UB_33      0.0490286000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5578
_diffrn_reflns_theta_full        71.96
_diffrn_reflns_theta_max         71.96
_diffrn_reflns_theta_min         4.15
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0561P)^2^+0.3433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                3157
_reflns_number_total             3215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np500302e_si_002.cif
_cod_data_source_block           exp_1614
_cod_depositor_comments
'Adding full bibliography for 1516470--1516471.cif.'
_cod_database_code               1516470
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97