#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:11:30 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257963 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240292.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_7240292
loop_
_publ_author_name
'Yin, Zhao-Kun'
'Feng, Zi-Ming'
'Jiang, Jian-Shuang'
'Zhang, Xu'
'Zhang, Pei-Cheng'
'Yang, Ya-Nan'
_publ_section_title
;
 New diterpenoid quinones derived from Salvia miltiorrhiza and their
 cytotoxic and neuroprotective activities
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              14235
_journal_page_last               14242
_journal_paper_doi               10.1039/D0RA02022B
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C19 H20 O5'
_chemical_formula_sum            'C19 H20 O5'
_chemical_formula_weight         328.35
_space_group_crystal_system      hexagonal
_space_group_IT_number           172
_space_group_name_Hall           'P 64'
_space_group_name_H-M_alt        'P 64'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-10
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2020-01-03 deposited with the CCDC.	2020-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   14.63788(16)
_cell_length_b                   14.63788(16)
_cell_length_c                   13.6616(2)
_cell_measurement_reflns_used    9375
_cell_measurement_temperature    109.90(10)
_cell_measurement_theta_max      70.9700
_cell_measurement_theta_min      3.4850
_cell_volume                     2535.06(5)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.90(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9301
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   12.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   24.0000  121.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega   57.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega   81.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega   90.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   41.00   86.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00  123.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega   71.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   89.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   88.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   95.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega  126.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega  126.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
 13 omega  125.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 14 omega   97.00  123.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   90.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   90.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   87.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   90.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   81.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   81.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   81.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   71.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   60.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   44.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 25 omega   32.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 26 omega   19.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 27 omega   14.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 28 omega   80.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   60.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 30 omega   57.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   -2.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 32 omega   16.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 33 omega  -21.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1086081000
_diffrn_orient_matrix_UB_12      -0.0935396000
_diffrn_orient_matrix_UB_13      -0.0281819000
_diffrn_orient_matrix_UB_21      0.0516233000
_diffrn_orient_matrix_UB_22      -0.0670915000
_diffrn_orient_matrix_UB_23      -0.0228145000
_diffrn_orient_matrix_UB_31      -0.0177086000
_diffrn_orient_matrix_UB_32      -0.0389786000
_diffrn_orient_matrix_UB_33      0.1067474000
_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  0.0262
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14929
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.127
_diffrn_reflns_theta_min         4.759
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79531
_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_density_diffrn    1.290
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0515P)²+0.2914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.883
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                3026
_reflns_number_total             3057
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra02022b2.cif
_cod_data_source_block           exp_6141
_cod_depositor_comments          'Adding full bibliography for 7240292.cif.'
_cod_original_cell_volume        2535.06(7)
_cod_database_code               7240292
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.803
_shelx_estimated_absorpt_t_min   0.749
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+2/3'
'-y, x-y, z+1/3'
'-x, -y, z'
'-x+y, -x, z+2/3'
'y, -x+y, z+1/3'
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 -1.00124(11) -0.19099(11) -0.31479(11) 0.0206(3) Uani 1 1 d . . . . .
O4 O -1.08040(10) -0.48496(11) -0.19234(10) 0.0194(3) Uani 1 1 d . . . . .
H4 H -1.0328 -0.5007 -0.1866 0.029 Uiso 0.5 1 calc R U P A -1
O5 O -1.09899(10) -0.52382(11) -0.03241(11) 0.0202(3) Uani 1 1 d . . . . .
H5 H -1.0366 -0.5108 -0.0394 0.030 Uiso 0.5 1 calc R U P B -2
O2 O -1.05261(11) -0.26184(11) -0.16530(11) 0.0220(3) Uani 1 1 d . . . . .
O3 O -1.37075(11) -0.49161(12) -0.16098(11) 0.0224(3) Uani 1 1 d . . . . .
C1 C -1.06537(15) -0.27083(15) -0.25220(15) 0.0175(4) Uani 1 1 d . . . . .
C7 C -1.12755(14) -0.32713(15) -0.40857(15) 0.0163(4) Uani 1 1 d . . . . .
C3 C -1.24372(14) -0.44670(14) -0.28521(15) 0.0166(4) Uani 1 1 d . . . . .
C4 C -1.31498(15) -0.49999(16) -0.36096(16) 0.0208(4) Uani 1 1 d . . . . .
H4A H -1.3798 -0.5619 -0.3462 0.025 Uiso 1 1 calc R U . . .
C15 C -1.23037(14) -0.50364(14) -0.10866(15) 0.0156(4) Uani 1 1 d . . . . .
C6 C -1.19983(15) -0.37424(16) -0.48379(15) 0.0190(4) Uani 1 1 d . . . . .
C8 C -1.02652(15) -0.22471(15) -0.41569(15) 0.0182(4) Uani 1 1 d . . . . .
H8 H -0.9707 -0.2376 -0.4432 0.022 Uiso 1 1 calc R U . . .
C16 C -1.29941(14) -0.53211(15) -0.01807(14) 0.0172(4) Uani 1 1 d . . . . .
H16 H -1.3219 -0.6060 0.0022 0.021 Uiso 1 1 calc R U . . .
C18 C -1.13074(14) -0.50318(14) -0.11176(15) 0.0152(4) Uani 1 1 d . . . . .
C2 C -1.14817(14) -0.35760(15) -0.31201(14) 0.0150(4) Uani 1 1 d . . . . .
C11 C -1.18102(16) -0.31856(18) -0.58199(16) 0.0243(4) Uani 1 1 d . . . . .
C14 C -1.27544(14) -0.48049(14) -0.18326(15) 0.0164(4) Uani 1 1 d . . . . .
C17 C -1.39511(15) -0.52738(17) -0.05984(15) 0.0223(4) Uani 1 1 d . . . . .
H17A H -1.4592 -0.5980 -0.0571 0.027 Uiso 1 1 calc R U . . .
H17B H -1.4080 -0.4778 -0.0211 0.027 Uiso 1 1 calc R U . . .
C10 C -1.07437(16) -0.21238(17) -0.58275(16) 0.0248(4) Uani 1 1 d . . . . .
H10A H -1.0178 -0.2268 -0.6027 0.030 Uiso 1 1 calc R U . . .
H10B H -1.0784 -0.1657 -0.6330 0.030 Uiso 1 1 calc R U . . .
C5 C -1.29365(16) -0.46475(16) -0.45781(16) 0.0225(4) Uani 1 1 d . . . . .
H5A H -1.3442 -0.5033 -0.5071 0.027 Uiso 1 1 calc R U . . .
C9 C -1.04331(16) -0.15305(16) -0.48465(16) 0.0226(4) Uani 1 1 d . . . . .
H9A H -0.9778 -0.0841 -0.4916 0.027 Uiso 1 1 calc R U . . .
H9B H -1.1002 -0.1411 -0.4603 0.027 Uiso 1 1 calc R U . . .
C19 C -1.24832(15) -0.45786(18) 0.06834(17) 0.0260(5) Uani 1 1 d . . . . .
H19A H -1.2217 -0.3849 0.0471 0.039 Uiso 1 1 calc R U . . .
H19B H -1.1897 -0.4655 0.0933 0.039 Uiso 1 1 calc R U . . .
H19C H -1.3007 -0.4754 0.1203 0.039 Uiso 1 1 calc R U . . .
C13 C -1.1812(2) -0.3879(2) -0.66605(18) 0.0390(6) Uani 1 1 d . . . . .
H13A H -1.2496 -0.4532 -0.6684 0.058 Uiso 1 1 calc R U . . .
H13B H -1.1251 -0.4050 -0.6554 0.058 Uiso 1 1 calc R U . . .
H13C H -1.1689 -0.3499 -0.7281 0.058 Uiso 1 1 calc R U . . .
C12 C -1.27102(18) -0.2937(2) -0.59719(19) 0.0363(6) Uani 1 1 d . . . . .
H12A H -1.2677 -0.2453 -0.5459 0.054 Uiso 1 1 calc R U . . .
H12B H -1.3392 -0.3592 -0.5939 0.054 Uiso 1 1 calc R U . . .
H12C H -1.2633 -0.2607 -0.6614 0.054 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C1 O1 C8 110.70(14) . . ?
C18 O4 H4 109.5 . . ?
C18 O5 H5 109.5 . . ?
C14 O3 C17 107.95(15) . . ?
O1 C1 C2 107.67(16) . . ?
O2 C1 O1 121.41(18) . . ?
O2 C1 C2 130.83(19) . . ?
C6 C7 C8 125.30(18) . . ?
C2 C7 C6 124.05(18) . . ?
C2 C7 C8 109.55(17) . . ?
C4 C3 C2 116.39(18) . . ?
C4 C3 C14 119.38(17) . . ?
C2 C3 C14 124.02(17) . . ?
C3 C4 H4A 119.1 . . ?
C3 C4 C5 121.90(18) . . ?
C5 C4 H4A 119.1 . . ?
C18 C15 C16 123.56(17) . . ?
C14 C15 C16 110.08(16) . . ?
C14 C15 C18 126.35(18) . . ?
C7 C6 C11 119.90(18) . . ?
C7 C6 C5 115.33(19) . . ?
C5 C6 C11 124.15(18) . . ?
O1 C8 C7 103.67(15) . . ?
O1 C8 H8 109.1 . . ?
O1 C8 C9 117.19(16) . . ?
C7 C8 H8 109.1 . . ?
C7 C8 C9 108.24(16) . . ?
C9 C8 H8 109.1 . . ?
C15 C16 H16 109.6 . . ?
C15 C16 C17 100.40(15) . . ?
C15 C16 C19 114.44(16) . . ?
C17 C16 H16 109.6 . . ?
C19 C16 H16 109.6 . . ?
C19 C16 C17 112.74(17) . . ?
O4 C18 C15 119.89(17) . . ?
O5 C18 O4 122.86(16) . . ?
O5 C18 C15 117.23(17) . . ?
C7 C2 C1 107.27(17) . . ?
C7 C2 C3 120.44(18) . . ?
C3 C2 C1 131.21(18) . . ?
C6 C11 C10 111.29(17) . . ?
C6 C11 C13 111.5(2) . . ?
C6 C11 C12 107.29(17) . . ?
C13 C11 C10 108.96(18) . . ?
C13 C11 C12 109.7(2) . . ?
C12 C11 C10 108.11(19) . . ?
O3 C14 C3 112.66(16) . . ?
C15 C14 O3 113.84(18) . . ?
C15 C14 C3 133.50(17) . . ?
O3 C17 C16 107.56(15) . . ?
O3 C17 H17A 110.2 . . ?
O3 C17 H17B 110.2 . . ?
C16 C17 H17A 110.2 . . ?
C16 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C9 C10 C11 115.07(17) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 C4 121.55(18) . . ?
C6 C5 H5A 119.2 . . ?
C8 C9 C10 104.77(16) . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 . . ?
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 . . ?
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 C1 1.372(2) . ?
O1 C8 1.449(2) . ?
O4 H4 0.8400 . ?
O4 C18 1.277(2) . ?
O5 H5 0.8400 . ?
O5 C18 1.274(2) . ?
O2 C1 1.199(3) . ?
O3 C14 1.356(2) . ?
O3 C17 1.457(2) . ?
C1 C2 1.487(3) . ?
C7 C6 1.386(3) . ?
C7 C8 1.492(3) . ?
C7 C2 1.377(3) . ?
C3 C4 1.398(3) . ?
C3 C2 1.403(3) . ?
C3 C14 1.473(3) . ?
C4 H4A 0.9500 . ?
C4 C5 1.398(3) . ?
C15 C16 1.518(3) . ?
C15 C18 1.456(2) . ?
C15 C14 1.346(3) . ?
C6 C11 1.522(3) . ?
C6 C5 1.396(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.519(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.546(2) . ?
C16 C19 1.524(3) . ?
C11 C10 1.558(3) . ?
C11 C13 1.532(3) . ?
C11 C12 1.547(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.537(3) . ?
C5 H5A 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
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 C1 C2 C7 2.09(19) . . . . ?
O1 C1 C2 C3 -165.71(18) . . . . ?
O1 C8 C9 C10 -176.97(15) . . . . ?
O2 C1 C2 C7 178.65(18) . . . . ?
O2 C1 C2 C3 10.8(3) . . . . ?
C1 O1 C8 C7 10.92(19) . . . . ?
C1 O1 C8 C9 130.07(17) . . . . ?
C7 C6 C11 C10 2.1(3) . . . . ?
C7 C6 C11 C13 124.0(2) . . . . ?
C7 C6 C11 C12 -116.0(2) . . . . ?
C7 C6 C5 C4 4.3(3) . . . . ?
C7 C8 C9 C10 -60.3(2) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C3 C2 C1 165.66(18) . . . . ?
C4 C3 C2 C7 -0.8(3) . . . . ?
C4 C3 C14 O3 -49.2(2) . . . . ?
C4 C3 C14 C15 129.9(2) . . . . ?
C15 C16 C17 O3 -3.9(2) . . . . ?
C6 C7 C8 O1 158.91(17) . . . . ?
C6 C7 C8 C9 33.8(3) . . . . ?
C6 C7 C2 C1 -163.77(17) . . . . ?
C6 C7 C2 C3 5.6(3) . . . . ?
C6 C11 C10 C9 -34.4(2) . . . . ?
C8 O1 C1 O2 174.65(17) . . . . ?
C8 O1 C1 C2 -8.40(19) . . . . ?
C8 C7 C6 C11 -2.7(3) . . . . ?
C8 C7 C6 C5 -173.95(17) . . . . ?
C8 C7 C2 C1 4.79(19) . . . . ?
C8 C7 C2 C3 174.16(16) . . . . ?
C16 C15 C18 O4 175.50(17) . . . . ?
C16 C15 C18 O5 -2.9(3) . . . . ?
C16 C15 C14 O3 -2.2(2) . . . . ?
C16 C15 C14 C3 178.77(19) . . . . ?
C18 C15 C16 C17 -175.85(17) . . . . ?
C18 C15 C16 C19 63.1(2) . . . . ?
C18 C15 C14 O3 177.33(17) . . . . ?
C18 C15 C14 C3 -1.7(3) . . . . ?
C2 C7 C6 C11 164.09(18) . . . . ?
C2 C7 C6 C5 -7.2(3) . . . . ?
C2 C7 C8 O1 -9.47(19) . . . . ?
C2 C7 C8 C9 -134.60(17) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C2 C3 C14 O3 125.34(19) . . . . ?
C2 C3 C14 C15 -55.6(3) . . . . ?
C11 C6 C5 C4 -166.5(2) . . . . ?
C11 C10 C9 C8 64.7(2) . . . . ?
C14 O3 C17 C16 3.0(2) . . . . ?
C14 C3 C4 C5 173.11(18) . . . . ?
C14 C3 C2 C1 -9.0(3) . . . . ?
C14 C3 C2 C7 -175.47(17) . . . . ?
C14 C15 C16 C17 3.7(2) . . . . ?
C14 C15 C16 C19 -117.32(19) . . . . ?
C14 C15 C18 O4 -4.0(3) . . . . ?
C14 C15 C18 O5 177.60(18) . . . . ?
C17 O3 C14 C3 178.70(16) . . . . ?
C17 O3 C14 C15 -0.6(2) . . . . ?
C5 C6 C11 C10 172.58(19) . . . . ?
C5 C6 C11 C13 -65.6(3) . . . . ?
C5 C6 C11 C12 54.5(3) . . . . ?
C19 C16 C17 O3 118.31(18) . . . . ?
C13 C11 C10 C9 -157.7(2) . . . . ?
C12 C11 C10 C9 83.2(2) . . . . ?
