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_1566301
_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 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_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
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.042(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.1550(4)
_cell_length_b                   9.2926(2)
_cell_length_c                   18.6842(5)
_cell_measurement_reflns_used    5458
_cell_measurement_temperature    114.25(10)
_cell_measurement_theta_max      69.7910
_cell_measurement_theta_min      4.5680
_cell_volume                     2361.96(11)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      114.25(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega   24.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000   30.0000 52

  2 omega   53.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -178.0000    0.0000 25

  3 omega   57.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -178.0000  -60.0000 33

  4 omega   67.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -178.0000 -150.0000 42

  5 omega   87.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 28

  6 omega   60.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 62

  7 omega   56.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 55

  8 omega   46.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 31

  9 omega   39.00  140.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000    0.0000 101

 10 omega  130.00  167.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 37

 11 omega   97.00  124.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 27

 12 omega   58.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -30.0000 36

 13 omega   10.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -60.0000 93

 14 omega   42.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   19.0000   30.0000 34

 15 omega   20.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000   60.0000 83

 16 omega   40.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 59

 17 omega   42.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 67

 18 omega   41.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 57

 19 omega   57.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 36

 20 omega   41.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 41

 21 omega   38.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 41

 22 omega   85.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 91

 23 omega   90.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 45

 24 omega   38.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 50

 25 omega   41.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 84

 26 omega   -7.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000    0.0000 36

 27 omega  -28.00    8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000   90.0000 36

 28 omega  -35.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -19.0000   30.0000 99

 29 omega  -22.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -180.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0228780000
_diffrn_orient_matrix_UB_12      0.0946555000
_diffrn_orient_matrix_UB_13      -0.0704388000
_diffrn_orient_matrix_UB_21      0.0570538000
_diffrn_orient_matrix_UB_22      0.1254192000
_diffrn_orient_matrix_UB_23      0.0461801000
_diffrn_orient_matrix_UB_31      0.0951722000
_diffrn_orient_matrix_UB_32      -0.0524955000
_diffrn_orient_matrix_UB_33      -0.0164052000
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16269
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.148
_diffrn_reflns_theta_min         4.926
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92215
_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    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0503P)^2^+0.8318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3807
_reflns_number_total             4520
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00849_si_001.cif
_cod_data_source_block           exp_7280
_cod_original_cell_volume        2361.96(12)
_cod_database_code               1566301
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C6") = Uanis(C6')
Uanis(C14") = Uanis(C14')
Uanis(C6B) = Uanis(C6)
Uanis(C14B) = Uanis(C14)
3. Others
 Sof(H5'C)=Sof(H5'D)=Sof(C6')=Sof(H6')=Sof(C14')=Sof(H14J)=Sof(H14K)=Sof(H14L)=
 1-FVAR(1)
 Sof(H5'A)=Sof(H5'B)=Sof(C6")=Sof(H6")=Sof(C14")=Sof(H14G)=Sof(H14H)=Sof(H14I)=
 FVAR(1)
 Sof(H5BC)=Sof(H5BD)=Sof(C6)=Sof(H6)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=1-
 FVAR(2)
 Sof(H5AA)=Sof(H5AB)=Sof(C6B)=Sof(H6B)=Sof(C14B)=Sof(H14D)=Sof(H14E)=Sof(H14F)=
 FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C6B(H6B), C10(H10), C6"(H6"), C6'(H6'), C10'(H10')
4.b Secondary CH2 refined with riding coordinates:
 C5(H5AA,H5AB), C5(H5BC,H5BD), C5'(H5'A,H5'B), C5'(H5'C,H5'D)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C13(H13), C3'(H3'), C13'(H13')
4.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C14B(H14D,H14E,
 H14F), C11'(H11D,H11E,H11F), C12'(H12D,H12E,H12F), C14"(H14G,H14H,H14I),
 C14'(H14J,H14K,H14L)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5)
;
_shelx_res_checksum              32651
_shelx_hkl_checksum              41461
_olex2_submission_special_instructions 'No special instructions were received'