Cadinane-Type Sesquiterpenoids with Cytotoxic Activity from the Infected Stems of the Semi-mangrove <i>Hibiscus tiliaceus</i>.
Chen, De-Li; Chen, Mei-Ying; Hou, Yong; Wang, Can-Hong; Sun, Zhao-Cui; Yang, Yun; Liang, Han-Qiao; Ma, Guo-Xu; Xu, Xu-Dong; Wei, Jian-He; Journal of natural products 85 (2022) 127–135; doi:10.1021/acs.jnatprod.1c00849

data_1566299
_publ_section_title
;
 Cadinane-Type Sesquiterpenoids with Cytotoxic Activity from the Infected
 Stems of the Semi-mangrove <i>Hibiscus tiliaceus</i>.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              127
_journal_page_last               135
_journal_paper_doi               10.1021/acs.jnatprod.1c00849
_journal_volume                  85
_journal_year                    2022
_chemical_formula_moiety         'C16 H18 O4'
_chemical_formula_sum            'C16 H18 O4'
_chemical_formula_weight         274.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-08-30
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.952(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.851(3)
_cell_length_b                   9.869(2)
_cell_length_c                   17.994(3)
_cell_measurement_reflns_used    381
_cell_measurement_temperature    112.55(10)
_cell_measurement_theta_max      24.1410
_cell_measurement_theta_min      3.4340
_cell_volume                     2811.1(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      112.55(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega    8.00   83.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   57.0000   90.0000 75

  2 omega  -10.00   82.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   77.0000 -180.0000 92

  3 omega   23.00   53.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -99.0000  -30.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0095188000
_diffrn_orient_matrix_UB_12      -0.0100859000
_diffrn_orient_matrix_UB_13      -0.0376960000
_diffrn_orient_matrix_UB_21      0.0429777000
_diffrn_orient_matrix_UB_22      0.0157292000
_diffrn_orient_matrix_UB_23      0.0090089000
_diffrn_orient_matrix_UB_31      0.0083021000
_diffrn_orient_matrix_UB_32      -0.0693924000
_diffrn_orient_matrix_UB_33      0.0075407000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.1865
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5411
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         3.280
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1895
_refine_ls_R_factor_gt           0.0738
_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^)+(0.0257P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1127
_reflns_number_total             2691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00849_si_005.cif
_cod_data_source_block           exp_7367
_cod_original_cell_volume        2811.2(9)
_cod_database_code               1566299
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.979
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C14(H14)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_res_checksum              45697
_shelx_hkl_checksum              57559
_olex2_submission_special_instructions 'No special instructions were received'