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_1566297
_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_absolute_configuration ad
_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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 99.486(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.70500(10)
_cell_length_b                   12.2221(3)
_cell_length_c                   12.1951(3)
_cell_measurement_reflns_used    5976
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.7740
_cell_measurement_theta_min      3.6090
_cell_volume                     691.69(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     34.00 108.00   0.50    0.05    --   47.51  57.00 150.00  148
  2  \w     25.00  81.00   0.50    0.05    --   47.51  77.00  60.00  112
  3  \w     43.00  93.00   0.50    0.05    --   47.51  37.00  60.00  100
  4  \w     51.00  97.00   0.50    0.05    --   47.51  29.00  -0.00   92
  5  \w   -104.00 -76.00   0.50    0.05    --  -47.51 -29.00-161.00   56
  6  \w    -68.00 -29.00   0.50    0.05    -- -101.00  61.00 -90.00   78
  7  \w   -113.00 -73.00   0.50    0.05    --  -47.51 -57.00  60.00   80
  8  \w    -68.00 -32.00   0.50    0.05    --  -47.51 -57.00  60.00   72
  9  \w     -2.00  23.00   0.50    0.05    --  -47.51  29.00  -0.00   50
 10  \w    121.00 146.00   0.50    0.05    --  106.68  29.00  -0.00   50
 11  \w    142.00 174.00   0.50    0.05    --  106.68  15.00 -30.00   64
 12  \w     94.00 135.00   0.50    0.05    --  106.68  15.00 -30.00   82
 13  \w     35.00  65.00   0.50    0.05    --  106.68 -61.00 -90.00   60
 14  \w     39.00  64.00   0.50    0.05    --  106.68 -61.00 -60.00   50
 15  \w     35.00  67.00   0.50    0.05    --  106.68 -61.00 -30.00   64
 16  \w     36.00  62.00   0.50    0.05    --  106.68 -61.00  30.00   52
 17  \w     35.00  71.00   0.50    0.05    --  106.68 -61.00  60.00   72
 18  \w     35.00  67.00   0.50    0.05    --  106.68 -61.00  90.00   64
 19  \w    -25.00  40.00   0.50    0.05    --   47.51 -37.00  60.00  130
 20  \w    -24.00  10.00   0.50    0.05    --   47.51 -29.00-161.00   68
 21  \w     37.00 106.00   0.50    0.05    --  106.68-125.00-180.00  138
 22  \w     50.00  94.00   0.50    0.05    --  106.68 -94.00-120.00   88
 23  \w     80.00 105.00   0.50    0.05    --  106.68 -94.00  30.00   50
 24  \w     43.00  68.00   0.50    0.05    --  106.68 -94.00  30.00   50
 25  \w   -119.00 -75.00   0.50    0.05    --  -47.51-125.00   0.00   88
 26  \w   -109.00 -78.00   0.50    0.05    -- -101.00 -77.00  90.00   62
 27  \w   -103.00 -78.00   0.50    0.05    -- -101.00 -77.00 120.00   50
 28  \w   -103.00 -78.00   0.50    0.05    -- -101.00 -77.00 150.00   50
 29  \w   -171.00-117.00   0.50    0.05    -- -101.00 -77.00 150.00  108
 30  \w   -153.00-128.00   0.50    0.05    -- -101.00 -77.00 120.00   50
 31  \w   -169.00-134.00   0.50    0.05    -- -101.00 -77.00  90.00   70
 32  \w   -166.00-138.00   0.50    0.05    -- -101.00 -64.00  56.80   56
 33  \w   -173.00-145.00   0.50    0.05    -- -101.00 -77.00  60.00   56
 34  \w   -173.00-147.00   0.50    0.05    -- -101.00 -61.00 120.00   52
 35  \w   -162.00 -82.00   0.50    0.05    -- -101.00 -71.00  76.31  160
 36  \w   -120.00 -82.00   0.50    0.05    -- -101.00 -77.00  60.00   76
 37  \w   -112.00 -85.00   0.50    0.05    -- -101.00 -61.00  90.00   54
 38  \w   -111.00 -84.00   0.50    0.05    -- -101.00 -64.00  56.80   54
 39  \w   -111.00 -84.00   0.50    0.05    -- -101.00 -61.00 120.00   54
 40  \w   -109.00 -84.00   0.50    0.05    -- -101.00 -61.00 150.00   50
 41  \w   -122.00 -84.00   0.50    0.05    -- -101.00 -61.00 135.97   76
 42  \w   -126.00 -88.00   0.50    0.05    -- -101.00 -45.00 150.00   76
 43  \w   -116.00 -87.00   0.50    0.05    -- -101.00 -43.00 132.62   58
 44  \w   -171.00-132.00   0.50    0.05    -- -101.00 -61.00 135.97   78
 45  \w   -122.00 -92.00   0.50    0.05    -- -101.00 -43.00  94.12   60
 46  \w   -155.00-129.00   0.50    0.05    -- -101.00 -29.00-161.00   52
 47  \w   -166.00-139.00   0.50    0.05    -- -101.00 -61.00-180.00   54
 48  \w   -120.00 -84.00   0.50    0.05    -- -101.00 -61.00-180.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0127388000
_diffrn_orient_matrix_UB_12      -0.0074880000
_diffrn_orient_matrix_UB_13      0.1268290000
_diffrn_orient_matrix_UB_21      0.3077230000
_diffrn_orient_matrix_UB_22      0.0472690000
_diffrn_orient_matrix_UB_23      0.0179279000
_diffrn_orient_matrix_UB_31      -0.1237148000
_diffrn_orient_matrix_UB_32      0.1166207000
_diffrn_orient_matrix_UB_33      0.0009655000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7745
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.478
_diffrn_reflns_theta_min         3.675
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1093 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2650
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0772P)^2^+0.0232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.888
_reflns_number_gt                2511
_reflns_number_total             2650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00849_si_004.cif
_cod_data_source_block           hjxc_a_4_4_auto
_cod_database_code               1566297
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H18O4
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.887
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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              66824
_shelx_hkl_checksum              1096
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.718