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_1566300
_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         'C14 H14 O4'
_chemical_formula_sum            'C14 H14 O4'
_chemical_formula_weight         246.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 100.903(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0059(12)
_cell_length_b                   12.3372(9)
_cell_length_c                   7.0592(6)
_cell_measurement_reflns_used    525
_cell_measurement_temperature    112.35(10)
_cell_measurement_theta_max      24.5120
_cell_measurement_theta_min      4.0970
_cell_volume                     1197.77(17)
_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      112.35(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega  -30.00   -3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.7727  -77.0000  -90.0000 27

  2 omega   30.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -99.0000  -30.0000 25

  3 omega    8.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   57.0000   30.0000 75

  4 omega   56.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  178.0000  -90.0000 25

  5 omega   -6.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   77.0000  120.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0334233000
_diffrn_orient_matrix_UB_12      0.0142495000
_diffrn_orient_matrix_UB_13      0.0849290000
_diffrn_orient_matrix_UB_21      -0.0392971000
_diffrn_orient_matrix_UB_22      0.0130170000
_diffrn_orient_matrix_UB_23      0.0462714000
_diffrn_orient_matrix_UB_31      -0.0006223000
_diffrn_orient_matrix_UB_32      -0.0541379000
_diffrn_orient_matrix_UB_33      0.0334118000
_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  0.0876
_diffrn_reflns_av_unetI/netI     0.1296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5677
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.962
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95521
_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    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1613
_refine_ls_R_factor_gt           0.0654
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0169P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1091
_reflns_number_total             2311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00849_si_002.cif
_cod_data_source_block           exp_7364
_cod_original_cell_volume        1197.76(17)
_cod_database_code               1566300
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.78
_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(H3), C5(H5), C14(H14)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              35127
_shelx_hkl_checksum              4446
_olex2_submission_special_instructions 'No special instructions were received'