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_1566298
_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         'C18 H24 O3'
_chemical_formula_sum            'C18 H24 O3'
_chemical_formula_weight         288.37
_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                 93.3800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.83200(10)
_cell_length_b                   11.04770(10)
_cell_length_c                   24.6078(3)
_cell_measurement_reflns_used    14076
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.6800
_cell_measurement_theta_min      3.5810
_cell_volume                     1582.73(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.970
_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     90.00 127.00   0.50    0.10    --  106.68  61.00 -60.00   74
  2  \w    130.00 156.00   0.50    0.10    --  106.68  45.00 -60.00   52
  3  \w     94.00 120.00   0.50    0.10    --  106.68  30.00 -60.00   52
  4  \w     95.00 129.00   0.50    0.10    --  106.68  45.00 -60.00   68
  5  \w    142.00 177.00   0.50    0.10    --  106.68  30.00 -60.00   70
  6  \w    138.00 172.00   0.50    0.10    --  106.68  45.00  90.00   68
  7  \w     84.00 168.00   0.50    0.10    --  106.68  77.00  30.00  168
  8  \w     89.00 178.00   0.50    0.10    --  106.68  86.00 -10.00  178
  9  \w    -27.00   7.00   0.50    0.05    --   47.76 -19.00-120.00   68
 10  \w     -6.00  45.00   0.50    0.05    --   47.76 -37.00 -90.00  102
 11  \w    -24.00  17.00   0.50    0.05    --   47.76 -19.00 -30.00   82
 12  \w     -4.00  29.00   0.50    0.05    --   47.76 -19.00 150.00   66
 13  \w     81.00 108.00   0.50    0.10    --  106.68-125.00-120.00   54
 14  \w     36.00 108.00   0.50    0.10    --  106.68-125.00   0.00  144
 15  \w    -23.00  62.00   0.50    0.05    --   47.76 -86.00-129.00  170
 16  \w     38.00  63.00   0.50    0.10    --  106.68-125.00-120.00   50
 17  \w     52.00 104.00   0.50    0.10    --  106.68 -94.00-150.00  104
 18  \w     59.00 101.00   0.50    0.10    --  106.68 -86.00-129.00   84
 19  \w     45.00  74.00   0.50    0.10    --  106.68 -61.00-120.00   58
 20  \w     53.00  97.00   0.50    0.10    --  106.68 -77.00 -30.00   88
 21  \w     35.00  74.00   0.50    0.10    --  106.68 -61.00  60.00   78
 22  \w    -20.00   6.00   0.50    0.05    --  -47.76  19.00   0.00   52
 23  \w   -102.00 -29.00   0.50    0.10    -- -101.00  77.00-180.00  146
 24  \w    -68.00 -37.00   0.50    0.10    -- -101.00  61.00 -30.00   62
 25  \w    -66.00 -28.00   0.50    0.10    -- -101.00  61.00-180.00   76
 26  \w    -59.00 -28.00   0.50    0.10    -- -101.00  61.00   0.00   62
 27  \w    -68.00 -29.00   0.50    0.10    -- -101.00  61.00  60.00   78
 28  \w    -65.00 -32.00   0.50    0.10    -- -101.00  61.00 120.00   66
 29  \w    -84.00 -30.00   0.50    0.10    -- -101.00 125.00 150.00  108
 30  \w    -72.00  22.00   0.50    0.05    --  -47.76  86.00 -10.00  188
 31  \w    -88.00 -62.00   0.50    0.10    -- -101.00  86.00 -10.00   52
 32  \w   -162.00 -87.00   0.50    0.10    -- -101.00 -15.00 120.00  150
 33  \w   -172.00-138.00   0.50    0.10    -- -101.00 -61.00 150.00   68
 34  \w   -119.00 -93.00   0.50    0.10    -- -101.00 -61.00 150.00   52
 35  \w   -173.00-100.00   0.50    0.10    -- -101.00 -61.00 120.00  146
 36  \w   -150.00 -94.00   0.50    0.10    -- -101.00 -61.00-180.00  112
 37  \w   -161.00-125.00   0.50    0.10    -- -101.00 -86.00-129.00   72
 38  \w   -112.00-105.50   0.50    0.05    --  -47.76-125.00 -60.00   13
;
_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      -0.2417148000
_diffrn_orient_matrix_UB_12      -0.0419077000
_diffrn_orient_matrix_UB_13      -0.0205079000
_diffrn_orient_matrix_UB_21      -0.1033857000
_diffrn_orient_matrix_UB_22      0.1167153000
_diffrn_orient_matrix_UB_23      0.0225753000
_diffrn_orient_matrix_UB_31      0.0300606000
_diffrn_orient_matrix_UB_32      0.0637534000
_diffrn_orient_matrix_UB_33      -0.0548025000
_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  0.0318
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18826
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.961
_diffrn_reflns_theta_min         3.599
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86386
_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 yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2682 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6316
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0471P)^2^+0.3264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                6072
_reflns_number_total             6316
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00849_si_003.cif
_cod_data_source_block           hjxc_i_2_11a_auto
_cod_database_code               1566298
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.927
_reflns_odcompleteness_completeness 99.90
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C10(H10), C11(H11), C16(H16), C25(H25), C26(H26), C28(H28),
 C34(H34), C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C24(H24A,H24B), C27(H27A,H27B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C40(H40A,
 H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              49547
_shelx_hkl_checksum              70273
_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 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.779