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_1516471
_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 H28 O4, H2 O'
_chemical_formula_sum            'C20 H30 O5'
_chemical_formula_weight         350.44
_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             2014-03-05
_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                   7.2054(3)
_cell_length_b                   8.0628(3)
_cell_length_c                   31.8423(11)
_cell_measurement_reflns_used    4182
_cell_measurement_temperature    97.20(10)
_cell_measurement_theta_max      71.9150
_cell_measurement_theta_min      5.5580
_cell_volume                     1849.90(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      97.20(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9703
_diffrn_measurement_details
;
  1 omega   33.00   70.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  -60.0000 37

  2 omega   12.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   19.0000   30.0000 108

  3 omega  147.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 31

  4 omega   91.00  117.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 26

  5 omega   91.00  169.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -90.0000 78

  6 omega   88.00  133.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 45

  7 omega   67.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -150.0000 111

  8 omega   54.00  125.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 71

  9 omega   40.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 45

 10 omega   57.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 51

 11 omega   46.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 26

 12 omega   43.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 30

 13 omega   -3.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -150.0000 60

 14 omega  -15.00   12.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  -60.0000 27

 15 omega   -4.00   21.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   90.0000 25

 16 omega   -4.00   42.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -180.0000 46

 17 omega   30.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  120.0000 64

 18 omega  -77.00  -32.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 45

 19 omega  -30.00   70.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 100

 20 omega  -13.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   30.0000 90

 21 omega  -13.00   51.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -90.0000 64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1533073000
_diffrn_orient_matrix_UB_12      -0.0670534000
_diffrn_orient_matrix_UB_13      0.0291581000
_diffrn_orient_matrix_UB_21      0.1165422000
_diffrn_orient_matrix_UB_22      -0.0489540000
_diffrn_orient_matrix_UB_23      -0.0385966000
_diffrn_orient_matrix_UB_31      0.0931107000
_diffrn_orient_matrix_UB_32      0.1721963000
_diffrn_orient_matrix_UB_33      0.0004140000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            8427
_diffrn_reflns_theta_full        71.94
_diffrn_reflns_theta_max         71.94
_diffrn_reflns_theta_min         5.56
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.27(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.2789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                3365
_reflns_number_total             3528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np500302e_si_003.cif
_cod_data_source_block           exp_1959
_cod_depositor_comments
'Adding full bibliography for 1516470--1516471.cif.'
_cod_database_code               1516471
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97