Dysiherbols A-C and Dysideanone E, Cytotoxic and NF-κB Inhibitory Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge.
Jiao, Wei-Hua; Shi, Guo-Hua; Xu, Ting-Ting; Chen, Guo-Dong; Gu, Bin-Bin; Wang, Zhuo; Peng, Shuang; Wang, Shu-Ping; Li, Jia; Han, Bing-Nan; Zhang, Wei; Lin, Hou-Wen; Journal of natural products 79 (2016) 406–411; doi:10.1021/acs.jnatprod.5b01079

data_1542411
_publ_section_title
;
 Dysiherbols A-C and Dysideanone E, Cytotoxic and NF-\kB Inhibitory
 Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              406
_journal_page_last               411
_journal_paper_doi               10.1021/acs.jnatprod.5b01079
_journal_volume                  79
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H28 O2'
_chemical_formula_sum            'C21 H28 O2'
_chemical_formula_weight         312.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.667(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4012(3)
_cell_length_b                   6.5192(2)
_cell_length_c                   12.5869(3)
_cell_measurement_reflns_used    3589
_cell_measurement_temperature    130
_cell_measurement_theta_max      68.71
_cell_measurement_theta_min      3.52
_cell_volume                     850.66(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6410
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.483
_diffrn_reflns_theta_min         3.523
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.7945.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 909 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0974P)^2^+0.0706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.603
_reflns_Friedel_fraction_full    0.705
_reflns_Friedel_fraction_max     0.692
_reflns_number_gt                2530
_reflns_number_total             2646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np5b01079_si_002.cif
_cod_data_source_block           cu_dm14635_0m
_cod_depositor_comments          'Adding full bibliography for 1542411.cif.'
_cod_database_code               1542411
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.943
_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.a Ternary CH refined with riding coordinates:
 C1(H1A), C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              17385
_shelx_hkl_checksum              8325
_olex2_submission_special_instructions 'No special instructions were received'