#------------------------------------------------------------------------------
#$Date: 2022-02-04 02:50:11 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272533 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/63/1566300.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1566300
loop_
_publ_author_name
'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'
_publ_section_title
;
 Cadinane-Type Sesquiterpenoids with Cytotoxic Activity from the Infected
 Stems of the Semi-mangrove Hibiscus tiliaceus.
;
_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
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   -3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.7727  -77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   30.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -99.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega    8.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   57.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega   56.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  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       'ω 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/[σ²(Fo²)+(0.0169P)²] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48140(16) 0.18480(17) -0.1472(4) 0.0311(7) Uani 1 1 d . . . . .
H1 H 0.462467 0.247644 -0.162600 0.047 Uiso 1 1 calc R U . . .
O2 O 0.49185(17) 0.39355(17) -0.1215(3) 0.0310(7) Uani 1 1 d . . . . .
O3 O 0.90775(17) 0.45885(17) 0.2448(4) 0.0352(7) Uani 1 1 d . . . . .
O8 O 0.77405(15) 0.36598(16) 0.1293(3) 0.0219(6) Uani 1 1 d . . . . .
C1 C 0.6271(2) 0.2805(2) -0.0056(5) 0.0183(8) Uani 1 1 d . . . . .
C2 C 0.5760(2) 0.1839(3) -0.0606(5) 0.0211(8) Uani 1 1 d . . . . .
C3 C 0.6222(2) 0.0838(2) -0.0312(5) 0.0211(8) Uani 1 1 d . . . . .
H3 H 0.587021 0.021169 -0.070807 0.025 Uiso 1 1 calc R U . . .
C4 C 0.7190(2) 0.0751(2) 0.0555(5) 0.0191(8) Uani 1 1 d . . . . .
C5 C 0.8729(2) 0.1740(3) 0.2134(5) 0.0208(8) Uani 1 1 d . . . . .
H5 H 0.905662 0.108743 0.242710 0.025 Uiso 1 1 calc R U . . .
C6 C 0.9209(2) 0.2667(3) 0.2620(5) 0.0215(8) Uani 1 1 d . . . . .
C7 C 0.8721(2) 0.3696(3) 0.2152(5) 0.0246(9) Uani 1 1 d . . . . .
C9 C 0.7260(2) 0.2699(2) 0.0817(5) 0.0175(8) Uani 1 1 d . . . . .
C10 C 0.7727(2) 0.1710(2) 0.1176(5) 0.0172(8) Uani 1 1 d . . . . .
C11 C 0.7672(2) -0.0353(2) 0.0897(5) 0.0226(8) Uani 1 1 d . . . . .
H11 H 0.836695 -0.025710 0.090472 0.027 Uiso 1 1 calc R U . . .
C12 C 0.7567(2) -0.0779(2) 0.2891(5) 0.0305(10) Uani 1 1 d . . . . .
H12A H 0.785968 -0.027444 0.386562 0.046 Uiso 1 1 calc R U . . .
H12B H 0.788619 -0.146828 0.311672 0.046 Uiso 1 1 calc R U . . .
H12C H 0.689038 -0.086010 0.293800 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7280(3) -0.1178(2) -0.0679(5) 0.0348(10) Uani 1 1 d . . . . .
H13A H 0.661182 -0.133581 -0.064405 0.052 Uiso 1 1 calc R U . . .
H13B H 0.765537 -0.183268 -0.046261 0.052 Uiso 1 1 calc R U . . .
H13C H 0.732570 -0.088403 -0.191692 0.052 Uiso 1 1 calc R U . . .
C14 C 0.5775(2) 0.3842(3) -0.0402(5) 0.0250(9) Uani 1 1 d . . . . .
H14 H 0.612202 0.446873 0.001258 0.030 Uiso 1 1 calc R U . . .
C15 C 1.0258(2) 0.2733(2) 0.3591(5) 0.0292(9) Uani 1 1 d . . . . .
H15A H 1.051039 0.201511 0.386476 0.044 Uiso 1 1 calc R U . . .
H15B H 1.031079 0.313228 0.477396 0.044 Uiso 1 1 calc R U . . .
H15C H 1.062246 0.309460 0.275582 0.044 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C9 O8 C7 122.1(2) . . ?
C2 C1 C9 116.6(3) . . ?
C2 C1 C14 119.8(3) . . ?
C9 C1 C14 123.6(3) . . ?
O1 C2 C1 121.5(3) . . ?
O1 C2 C3 117.6(3) . . ?
C3 C2 C1 120.9(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C10 119.2(3) . . ?
C3 C4 C11 120.6(3) . . ?
C10 C4 C11 120.2(3) . . ?
C6 C5 H5 118.6 . . ?
C6 C5 C10 122.7(3) . . ?
C10 C5 H5 118.6 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 C15 124.4(3) . . ?
C7 C6 C15 115.8(3) . . ?
O3 C7 O8 116.4(3) . . ?
O3 C7 C6 126.6(3) . . ?
O8 C7 C6 117.0(3) . . ?
O8 C9 C1 115.0(3) . . ?
O8 C9 C10 121.5(3) . . ?
C10 C9 C1 123.5(3) . . ?
C4 C10 C5 125.2(3) . . ?
C9 C10 C4 118.1(3) . . ?
C9 C10 C5 116.7(3) . . ?
C4 C11 H11 107.7 . . ?
C4 C11 C12 109.7(3) . . ?
C4 C11 C13 113.2(3) . . ?
C12 C11 H11 107.7 . . ?
C13 C11 H11 107.7 . . ?
C13 C11 C12 110.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C1 123.5(3) . . ?
O2 C14 H14 118.3 . . ?
C1 C14 H14 118.3 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C2 1.350(4) . ?
O2 C14 1.233(4) . ?
O3 C7 1.210(3) . ?
O8 C7 1.393(4) . ?
O8 C9 1.373(3) . ?
C1 C2 1.408(4) . ?
C1 C9 1.411(4) . ?
C1 C14 1.454(4) . ?
C2 C3 1.391(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 C10 1.426(4) . ?
C4 C11 1.519(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.339(4) . ?
C5 C10 1.438(4) . ?
C6 C7 1.451(4) . ?
C6 C15 1.501(4) . ?
C9 C10 1.385(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.535(4) . ?
C11 C13 1.531(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 179.7(3) . . . . ?
O8 C9 C10 C4 -177.0(3) . . . . ?
O8 C9 C10 C5 2.2(4) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C1 C9 C10 C4 2.7(5) . . . . ?
C1 C9 C10 C5 -178.0(3) . . . . ?
C2 C1 C9 O8 178.5(3) . . . . ?
C2 C1 C9 C10 -1.2(5) . . . . ?
C2 C1 C14 O2 -2.1(5) . . . . ?
C2 C3 C4 C10 0.5(5) . . . . ?
C2 C3 C4 C11 178.7(3) . . . . ?
C3 C4 C10 C5 178.5(3) . . . . ?
C3 C4 C10 C9 -2.3(5) . . . . ?
C3 C4 C11 C12 -90.4(4) . . . . ?
C3 C4 C11 C13 33.9(4) . . . . ?
C5 C6 C7 O3 -177.3(4) . . . . ?
C5 C6 C7 O8 3.4(5) . . . . ?
C6 C5 C10 C4 177.4(3) . . . . ?
C6 C5 C10 C9 -1.8(5) . . . . ?
C7 O8 C9 C1 -179.5(3) . . . . ?
C7 O8 C9 C10 0.2(4) . . . . ?
C9 O8 C7 O3 177.6(3) . . . . ?
C9 O8 C7 C6 -3.1(4) . . . . ?
C9 C1 C2 O1 -179.3(3) . . . . ?
C9 C1 C2 C3 -0.7(5) . . . . ?
C9 C1 C14 O2 177.9(3) . . . . ?
C10 C4 C11 C12 87.8(4) . . . . ?
C10 C4 C11 C13 -147.9(3) . . . . ?
C10 C5 C6 C7 -1.0(5) . . . . ?
C10 C5 C6 C15 -179.0(3) . . . . ?
C11 C4 C10 C5 0.3(5) . . . . ?
C11 C4 C10 C9 179.5(3) . . . . ?
C14 C1 C2 O1 0.6(5) . . . . ?
C14 C1 C2 C3 179.2(3) . . . . ?
C14 C1 C9 O8 -1.4(5) . . . . ?
C14 C1 C9 C10 178.8(3) . . . . ?
C15 C6 C7 O3 0.8(5) . . . . ?
C15 C6 C7 O8 -178.5(3) . . . . ?
