##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     CRYSTALS_ver_12.87
_journal_date_recd_electronic     2012-02-23
_journal_date_accepted     2012-03-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o1091
_journal_page_last     o1092
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812010756
_journal_coeditor_code     KP2392
_publ_contact_author_name     'Ee, Gwendoline Cheng Lian'
_publ_contact_author_address
;
Department of Chemistry, Faculty of Science, Universiti Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
_publ_contact_author_email     'gwen@science.upm.edu.my'
_publ_contact_author_fax     '+603 89435380'
_publ_contact_author_phone     '+603 89466785'
_publ_section_title
;\
<i>rac</i>-[3-Hydroxy-6,9-dimethyl-6-(4-methylpent-3-en-1-yl)-6a,7,8,9,10,10a-\
hexahydro-6<i>H</i>-1,9-epoxybenzo[<i>c</i>]chromen-4-yl](phenyl)methanone
;
loop_
    _publ_author_name
    _publ_author_address
    'Ee, Gwendoline Cheng Lian'
;
Department Chemistry, Faculty Science, University Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
    'Teh, Soek Sin'
;
Department Chemistry, Faculty Science, University Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
    'Kwong, Huey Chong '
;
Department Chemistry, Faculty Science, University Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
    'Mohamed Tahir, Mohamed Ibrahim'
;
Department Chemistry, Faculty Science, University Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
    'Mah, Siau Hui'
;
Department Chemistry, Faculty Science, Universiti Putra Malaysia,
43400 UPM Serdang, Selangor, Malaysia
;
_cell_special_details     ?
data_I
_chemical_name_systematic
;
<i>rac</i>-[3-Hydroxy-6,9-dimethyl-6-(4-methylpent-3-en-1-yl)-6a,7,8,9,10,10a-
hexahydro-6<i>H</i>-1,9-epoxybenzo[<i>c</i>]chromen-4-yl](phenyl)methanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C28 H32 O4'
_chemical_formula_sum     'C28 H32 O4'
_chemical_formula_iupac     'C28 H32 O4'
_chemical_formula_weight     432.56
_chemical_melting_point     483
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1 '
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
_cell_length_a     6.2022(4)
_cell_length_b     7.5220(4)
_cell_length_c     24.7673(15)
_cell_angle_alpha     98.410(5)
_cell_angle_beta     94.425(5)
_cell_angle_gamma     94.200(5)
_cell_volume     1135.43(12)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4627
_cell_measurement_theta_min     4
_cell_measurement_theta_max     71
_cell_measurement_temperature     150
_exptl_crystal_description     'needle'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.290
_exptl_crystal_size_mid     0.090
_exptl_crystal_size_min     0.050
_exptl_crystal_density_diffrn     1.265
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     464
_exptl_absorpt_coefficient_mu     0.661
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2006)
;
_exptl_absorpt_correction_T_min     0.9422
_exptl_absorpt_correction_T_max     0.9675
_exptl_special_details
;
;
_diffrn_ambient_temperature     150
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Oxford Diffraction Gemin area-detector'
_diffrn_measurement_device     'Oxford Diffraction Gemini'
_diffrn_measurement_method     \w/2\q
_diffrn_reflns_number     15011
_diffrn_reflns_av_R_equivalents     0.034
_diffrn_reflns_av_sigmaI/netI     ?
_diffrn_reflns_theta_min     3.622
_diffrn_reflns_theta_max     71.240
_diffrn_reflns_theta_full     67.678
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     30
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
For this compound, 15011 numbers of reflections were collected and measured
during the refinement. Symmetry related reflections were measured more than
once and after merging the symmetry equivalent reflections there were only
4340 reflection left. 19 more reflections were filtered, as \s cutoff was set
as -3 and (sin<i>\q</i>/<i>x</i>)set to>0.01 (to eliminate reflection measured
near the vicinity of beam stop) therefore numbers of reflection reduced to
4321.
;
_reflns_number_total     4340
_reflns_number_gt     3423
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0619
_refine_ls_R_factor_gt     0.0461
_refine_ls_wR_factor_all     0.1168
_refine_ls_wR_factor_gt     0.1054
_refine_ls_wR_factor_ref     0.1165
_refine_ls_goodness_of_fit_ref     0.9960
_refine_ls_number_reflns     4321
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.61P], where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.0004694
_refine_ls_shift/su_mean     0.0002104
_refine_diff_density_max     0.39
_refine_diff_density_min     -0.34
_refine_ls_extinction_method     'None'
loop_
    _atom_type_symbol
    _atom_type_scat_Cromer_Mann_a1
    _atom_type_scat_Cromer_Mann_a2
    _atom_type_scat_Cromer_Mann_a3
    _atom_type_scat_Cromer_Mann_a4
    _atom_type_scat_Cromer_Mann_b1
    _atom_type_scat_Cromer_Mann_b2
    _atom_type_scat_Cromer_Mann_b3
    _atom_type_scat_Cromer_Mann_b4
    _atom_type_scat_Cromer_Mann_c
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 2.3100 1.0200 1.5886 0.8650 20.8439 10.2075 0.5687 51.6512 0.2156 0.0181
                                                                          0.0091
                                'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.4930 0.3229 0.1402 0.0408 10.5109 26.1257 3.1424 57.7998 0.0030 0.0000
                                                                          0.0000
                                'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 3.0485 2.2868 1.5463 0.8670 13.2771 5.7011 0.3239 32.9089 0.2508 0.0492
                                                                          0.0322
                                'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement     'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution     'SIR92 (Altomare <i>et al.</i>, 1994)'
_computing_structure_refinement     'CRYSTALS (Betteridge <i>et al.</i>, 2003)'
_computing_molecular_graphics     'Mercury (Macrae <i>et al.</i>, 2006)'
_computing_publication_material     'CRYSTALS (Betteridge <i>et al.</i>, 2003)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _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_disorder_assembly
    _atom_site_disorder_group
    O O1 1.3916(2) 0.62936(17) 0.77877(5) 0.0320 Uani 1.0000 . .
    C C2 1.2067(3) 0.5510(2) 0.76653(7) 0.0250 Uani 1.0000 . .
    C C3 1.1384(3) 0.4954(2) 0.70701(7) 0.0263 Uani 1.0000 . .
    C C4 0.9367(3) 0.5313(2) 0.68404(8) 0.0291 Uani 1.0000 . .
    C C5 0.8872(3) 0.4939(3) 0.62773(8) 0.0365 Uani 1.0000 . .
    C C6 1.0351(4) 0.4162(3) 0.59461(8) 0.0431 Uani 1.0000 . .
    C C7 1.2346(4) 0.3778(3) 0.61725(9) 0.0447 Uani 1.0000 . .
    C C8 1.2880(3) 0.4204(3) 0.67332(8) 0.0355 Uani 1.0000 . .
    C C9 1.0615(3) 0.5227(2) 0.80880(7) 0.0235 Uani 1.0000 . .
    C C10 1.1140(3) 0.6170(2) 0.86326(7) 0.0255 Uani 1.0000 . .
    O O11 1.2907(2) 0.73655(17) 0.87537(5) 0.0336 Uani 1.0000 . .
    C C12 0.9944(3) 0.5844(2) 0.90629(7) 0.0267 Uani 1.0000 . .
    C C13 0.8146(3) 0.4582(2) 0.89609(7) 0.0239 Uani 1.0000 . .
    O O14 0.7243(2) 0.40329(16) 0.93968(5) 0.0282 Uani 1.0000 . .
    C C15 0.5848(3) 0.2316(2) 0.92940(7) 0.0255 Uani 1.0000 . .
    C C16 0.7221(3) 0.0698(2) 0.91977(7) 0.0263 Uani 1.0000 . .
    C C17 0.8289(3) 0.0419(2) 0.86545(7) 0.0251 Uani 1.0000 . .
    C C18 0.6761(3) 0.0648(2) 0.81520(7) 0.0224 Uani 1.0000 . .
    C C19 0.7858(3) 0.0839(2) 0.76156(7) 0.0235 Uani 1.0000 . .
    O O20 0.82634(19) 0.27776(16) 0.75412(5) 0.0252 Uani 1.0000 . .
    C C21 0.8751(3) 0.3983(2) 0.80136(7) 0.0220 Uani 1.0000 . .
    C C22 0.7405(3) 0.3818(2) 0.84248(7) 0.0222 Uani 1.0000 . .
    C C23 0.5588(3) 0.2361(2) 0.82988(7) 0.0217 Uani 1.0000 . .
    C C24 0.4288(3) 0.2301(2) 0.87914(7) 0.0252 Uani 1.0000 . .
    C C25 0.6276(3) 0.0004(2) 0.71244(7) 0.0263 Uani 1.0000 . .
    C C26 0.6933(3) 0.0294(3) 0.65592(8) 0.0363 Uani 1.0000 . .
    C C27 0.5303(3) -0.0667(3) 0.61092(8) 0.0320 Uani 1.0000 . .
    C C28 0.5695(3) -0.1476(3) 0.56176(7) 0.0294 Uani 1.0000 . .
    C C29 0.3899(3) -0.2423(3) 0.52118(8) 0.0404 Uani 1.0000 . .
    C C30 0.7924(3) -0.1539(3) 0.54199(9) 0.0430 Uani 1.0000 . .
    C C31 1.0059(3) 0.0067(3) 0.75961(8) 0.0304 Uani 1.0000 . .
    C C32 0.4671(3) 0.2328(3) 0.98082(8) 0.0319 Uani 1.0000 . .
    H H41 0.8314 0.5832 0.7073 0.0367 Uiso 1.0000 . .
    H H51 0.7488 0.5234 0.6122 0.0454 Uiso 1.0000 . .
    H H61 0.9999 0.3875 0.5557 0.0533 Uiso 1.0000 . .
    H H71 1.3367 0.3232 0.5942 0.0547 Uiso 1.0000 . .
    H H81 1.4295 0.3981 0.6891 0.0457 Uiso 1.0000 . .
    H H121 1.0361 0.6440 0.9423 0.0345 Uiso 1.0000 . .
    H H161 0.8374 0.0796 0.9503 0.0335 Uiso 1.0000 . .
    H H162 0.6217 -0.0382 0.9209 0.0328 Uiso 1.0000 . .
    H H171 0.9603 0.1294 0.8679 0.0317 Uiso 1.0000 . .
    H H172 0.8805 -0.0812 0.8599 0.0324 Uiso 1.0000 . .
    H H181 0.5662 -0.0425 0.8070 0.0291 Uiso 1.0000 . .
    H H231 0.4619 0.2584 0.7977 0.0269 Uiso 1.0000 . .
    H H241 0.3411 0.3350 0.8846 0.0319 Uiso 1.0000 . .
    H H242 0.3299 0.1190 0.8740 0.0317 Uiso 1.0000 . .
    H H251 0.6091 -0.1324 0.7137 0.0342 Uiso 1.0000 . .
    H H252 0.4852 0.0508 0.7176 0.0341 Uiso 1.0000 . .
    H H261 0.8365 -0.0145 0.6505 0.0461 Uiso 1.0000 . .
    H H262 0.7055 0.1603 0.6535 0.0467 Uiso 1.0000 . .
    H H271 0.3814 -0.0696 0.6200 0.0408 Uiso 1.0000 . .
    H H291 0.3915 -0.1929 0.4867 0.0632 Uiso 1.0000 . .
    H H292 0.4065 -0.3713 0.5141 0.0633 Uiso 1.0000 . .
    H H293 0.2496 -0.2260 0.5358 0.0628 Uiso 1.0000 . .
    H H301 0.7949 -0.1071 0.5070 0.0677 Uiso 1.0000 . .
    H H302 0.8301 -0.2777 0.5363 0.0685 Uiso 1.0000 . .
    H H303 0.9008 -0.0786 0.5679 0.0685 Uiso 1.0000 . .
    H H311 1.0584 0.0141 0.7238 0.0482 Uiso 1.0000 . .
    H H312 1.1094 0.0772 0.7879 0.0485 Uiso 1.0000 . .
    H H313 0.9902 -0.1190 0.7658 0.0489 Uiso 1.0000 . .
    H H323 0.3689 0.1245 0.9770 0.0491 Uiso 1.0000 . .
    H H322 0.5668 0.2357 1.0134 0.0499 Uiso 1.0000 . .
    H H321 0.3815 0.3378 0.9856 0.0494 Uiso 1.0000 . .
    H H111 1.3748 0.7225 0.8486 0.0530 Uiso 1.0000 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0270(7) 0.0331(7) 0.0343(7) -0.0087(6) 0.0017(5) 0.0060(6)
    C2 0.0252(9) 0.0171(9) 0.0327(10) -0.0010(7) 0.0009(7) 0.0060(7)
    C3 0.0282(9) 0.0220(9) 0.0289(9) -0.0045(7) 0.0043(7) 0.0067(7)
    C4 0.0316(10) 0.0255(10) 0.0307(10) -0.0008(8) 0.0052(8) 0.0064(8)
    C5 0.0369(11) 0.0391(12) 0.0333(11) -0.0020(9) -0.0017(8) 0.0103(9)
    C6 0.0479(13) 0.0531(14) 0.0259(10) -0.0068(11) 0.0022(9) 0.0043(9)
    C7 0.0419(12) 0.0568(14) 0.0341(11) 0.0006(10) 0.0143(9) -0.0010(10)
    C8 0.0297(10) 0.0410(12) 0.0356(11) 0.0000(9) 0.0073(8) 0.0046(9)
    C9 0.0252(9) 0.0196(9) 0.0257(9) 0.0003(7) 0.0007(7) 0.0045(7)
    C10 0.0263(9) 0.0182(9) 0.0308(10) -0.0024(7) -0.0020(7) 0.0047(7)
    O11 0.0342(7) 0.0309(7) 0.0319(7) -0.0133(6) -0.0005(6) 0.0020(6)
    C12 0.0331(10) 0.0213(9) 0.0233(9) -0.0015(8) -0.0005(7) -0.0012(7)
    C13 0.0263(9) 0.0201(9) 0.0254(9) 0.0025(7) 0.0052(7) 0.0020(7)
    O14 0.0326(7) 0.0272(7) 0.0227(6) -0.0052(5) 0.0049(5) -0.0005(5)
    C15 0.0246(9) 0.0251(9) 0.0256(9) -0.0033(7) 0.0036(7) 0.0024(7)
    C16 0.0254(9) 0.0280(10) 0.0257(9) -0.0002(7) -0.0001(7) 0.0071(7)
    C17 0.0241(9) 0.0220(9) 0.0295(9) 0.0022(7) 0.0025(7) 0.0050(7)
    C18 0.0211(8) 0.0197(9) 0.0254(9) -0.0023(7) 0.0034(7) 0.0014(7)
    C19 0.0224(9) 0.0199(9) 0.0264(9) -0.0036(7) 0.0031(7) 0.0003(7)
    O20 0.0300(7) 0.0226(6) 0.0213(6) -0.0055(5) 0.0033(5) 0.0009(5)
    C21 0.0234(8) 0.0189(9) 0.0228(9) 0.0008(7) -0.0009(7) 0.0025(7)
    C22 0.0224(8) 0.0188(9) 0.0254(9) 0.0026(7) 0.0010(7) 0.0035(7)
    C23 0.0191(8) 0.0231(9) 0.0228(9) 0.0004(7) 0.0006(7) 0.0039(7)
    C24 0.0220(9) 0.0269(9) 0.0266(9) 0.0012(7) 0.0033(7) 0.0037(7)
    C25 0.0247(9) 0.0247(9) 0.0270(9) -0.0038(7) 0.0030(7) -0.0013(7)
    C26 0.0315(10) 0.0470(13) 0.0264(10) -0.0084(9) 0.0046(8) -0.0027(9)
    C27 0.0267(9) 0.0387(11) 0.0291(10) -0.0007(8) 0.0037(8) 0.0011(8)
    C28 0.0323(10) 0.0303(10) 0.0254(9) 0.0032(8) 0.0012(8) 0.0040(8)
    C29 0.0416(12) 0.0440(13) 0.0321(11) 0.0039(10) -0.0013(9) -0.0041(9)
    C30 0.0398(12) 0.0566(14) 0.0316(11) 0.0061(10) 0.0092(9) -0.0002(10)
    C31 0.0249(9) 0.0349(11) 0.0296(10) 0.0009(8) 0.0043(7) -0.0015(8)
    C32 0.0332(10) 0.0350(11) 0.0277(10) -0.0017(8) 0.0076(8) 0.0050(8)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C2 . . 1.245(2) no
    C2 C3 . . 1.492(3) no
    C2 C9 . . 1.461(2) no
    C3 C4 . . 1.395(3) no
    C3 C8 . . 1.391(3) no
    C4 C5 . . 1.388(3) no
    C4 H41 . . 0.969 no
    C5 C6 . . 1.382(3) no
    C5 H51 . . 0.967 no
    C6 C7 . . 1.386(3) no
    C6 H61 . . 0.961 no
    C7 C8 . . 1.387(3) no
    C7 H71 . . 0.959 no
    C8 H81 . . 0.969 no
    C9 C10 . . 1.431(2) no
    C9 C21 . . 1.416(2) no
    C10 O11 . . 1.351(2) no
    C10 C12 . . 1.385(2) no
    O11 H111 . . 0.874 no
    C12 C13 . . 1.393(2) no
    C12 H121 . . 0.945 no
    C13 O14 . . 1.357(2) no
    C13 C22 . . 1.396(2) no
    O14 C15 . . 1.479(2) no
    C15 C16 . . 1.536(2) no
    C15 C24 . . 1.515(2) no
    C15 C32 . . 1.515(2) no
    C16 C17 . . 1.539(2) no
    C16 H161 . . 0.991 no
    C16 H162 . . 0.992 no
    C17 C18 . . 1.543(2) no
    C17 H171 . . 1.001 no
    C17 H172 . . 0.996 no
    C18 C19 . . 1.559(2) no
    C18 C23 . . 1.537(2) no
    C18 H181 . . 1.004 no
    C19 O20 . . 1.502(2) no
    C19 C25 . . 1.530(2) no
    C19 C31 . . 1.523(2) no
    O20 C21 . . 1.370(2) no
    C21 C22 . . 1.379(2) no
    C22 C23 . . 1.494(2) no
    C23 C24 . . 1.518(2) no
    C23 H231 . . 1.003 no
    C24 H241 . . 0.990 no
    C24 H242 . . 0.986 no
    C25 C26 . . 1.529(2) no
    C25 H251 . . 1.002 no
    C25 H252 . . 0.996 no
    C26 C27 . . 1.506(3) no
    C26 H261 . . 0.982 no
    C26 H262 . . 0.993 no
    C27 C28 . . 1.328(3) no
    C27 H271 . . 0.967 no
    C28 C29 . . 1.503(3) no
    C28 C30 . . 1.504(3) no
    C29 H291 . . 0.981 no
    C29 H292 . . 0.975 no
    C29 H293 . . 0.977 no
    C30 H301 . . 0.982 no
    C30 H302 . . 0.970 no
    C30 H303 . . 0.978 no
    C31 H311 . . 0.976 no
    C31 H312 . . 0.978 no
    C31 H313 . . 0.979 no
    C32 H323 . . 0.969 no
    C32 H322 . . 0.975 no
    C32 H321 . . 0.982 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C2 C3 . . . 116.89(16) no
    O1 C2 C9 . . . 120.99(16) no
    C3 C2 C9 . . . 122.07(15) no
    C2 C3 C4 . . . 121.53(16) no
    C2 C3 C8 . . . 118.50(16) no
    C4 C3 C8 . . . 119.73(17) no
    C3 C4 C5 . . . 119.91(18) no
    C3 C4 H41 . . . 120.2 no
    C5 C4 H41 . . . 119.9 no
    C4 C5 C6 . . . 120.00(19) no
    C4 C5 H51 . . . 119.1 no
    C6 C5 H51 . . . 120.9 no
    C5 C6 C7 . . . 120.37(19) no
    C5 C6 H61 . . . 120.2 no
    C7 C6 H61 . . . 119.4 no
    C6 C7 C8 . . . 119.9(2) no
    C6 C7 H71 . . . 120.2 no
    C8 C7 H71 . . . 119.9 no
    C3 C8 C7 . . . 120.02(19) no
    C3 C8 H81 . . . 119.9 no
    C7 C8 H81 . . . 120.1 no
    C2 C9 C10 . . . 119.22(15) no
    C2 C9 C21 . . . 124.97(16) no
    C10 C9 C21 . . . 115.68(15) no
    C9 C10 O11 . . . 120.83(16) no
    C9 C10 C12 . . . 122.15(16) no
    O11 C10 C12 . . . 116.94(16) no
    C10 O11 H111 . . . 109.2 no
    C10 C12 C13 . . . 119.00(16) no
    C10 C12 H121 . . . 120.7 no
    C13 C12 H121 . . . 120.2 no
    C12 C13 O14 . . . 118.03(15) no
    C12 C13 C22 . . . 120.50(16) no
    O14 C13 C22 . . . 121.31(16) no
    C13 O14 C15 . . . 117.10(13) no
    O14 C15 C16 . . . 110.88(14) no
    O14 C15 C24 . . . 109.24(14) no
    C16 C15 C24 . . . 108.97(14) no
    O14 C15 C32 . . . 103.92(14) no
    C16 C15 C32 . . . 112.01(15) no
    C24 C15 C32 . . . 111.74(15) no
    C15 C16 C17 . . . 116.82(14) no
    C15 C16 H161 . . . 109.1 no
    C17 C16 H161 . . . 108.3 no
    C15 C16 H162 . . . 105.6 no
    C17 C16 H162 . . . 108.1 no
    H161 C16 H162 . . . 108.7 no
    C16 C17 C18 . . . 113.52(14) no
    C16 C17 H171 . . . 109.4 no
    C18 C17 H171 . . . 108.8 no
    C16 C17 H172 . . . 108.9 no
    C18 C17 H172 . . . 109.1 no
    H171 C17 H172 . . . 106.9 no
    C17 C18 C19 . . . 116.21(14) no
    C17 C18 C23 . . . 108.18(14) no
    C19 C18 C23 . . . 106.99(13) no
    C17 C18 H181 . . . 108.4 no
    C19 C18 H181 . . . 107.7 no
    C23 C18 H181 . . . 109.2 no
    C18 C19 O20 . . . 111.90(13) no
    C18 C19 C25 . . . 108.74(14) no
    O20 C19 C25 . . . 104.37(13) no
    C18 C19 C31 . . . 113.70(14) no
    O20 C19 C31 . . . 105.61(13) no
    C25 C19 C31 . . . 112.13(14) no
    C19 O20 C21 . . . 115.62(12) no
    C9 C21 O20 . . . 121.81(15) no
    C9 C21 C22 . . . 122.22(16) no
    O20 C21 C22 . . . 115.80(15) no
    C13 C22 C21 . . . 118.67(16) no
    C13 C22 C23 . . . 122.24(15) no
    C21 C22 C23 . . . 116.14(15) no
    C18 C23 C22 . . . 103.24(13) no
    C18 C23 C24 . . . 112.94(14) no
    C22 C23 C24 . . . 110.36(14) no
    C18 C23 H231 . . . 110.6 no
    C22 C23 H231 . . . 109.6 no
    C24 C23 H231 . . . 109.9 no
    C23 C24 C15 . . . 108.64(14) no
    C23 C24 H241 . . . 110.7 no
    C15 C24 H241 . . . 109.7 no
    C23 C24 H242 . . . 110.5 no
    C15 C24 H242 . . . 108.7 no
    H241 C24 H242 . . . 108.4 no
    C19 C25 C26 . . . 116.47(15) no
    C19 C25 H251 . . . 106.8 no
    C26 C25 H251 . . . 108.8 no
    C19 C25 H252 . . . 107.8 no
    C26 C25 H252 . . . 108.3 no
    H251 C25 H252 . . . 108.4 no
    C25 C26 C27 . . . 111.43(16) no
    C25 C26 H261 . . . 109.8 no
    C27 C26 H261 . . . 109.3 no
    C25 C26 H262 . . . 109.7 no
    C27 C26 H262 . . . 109.1 no
    H261 C26 H262 . . . 107.4 no
    C26 C27 C28 . . . 127.51(18) no
    C26 C27 H271 . . . 114.7 no
    C28 C27 H271 . . . 117.8 no
    C27 C28 C29 . . . 121.68(18) no
    C27 C28 C30 . . . 123.77(18) no
    C29 C28 C30 . . . 114.55(17) no
    C28 C29 H291 . . . 110.1 no
    C28 C29 H292 . . . 110.3 no
    H291 C29 H292 . . . 109.4 no
    C28 C29 H293 . . . 109.9 no
    H291 C29 H293 . . . 109.0 no
    H292 C29 H293 . . . 108.0 no
    C28 C30 H301 . . . 110.0 no
    C28 C30 H302 . . . 109.5 no
    H301 C30 H302 . . . 108.5 no
    C28 C30 H303 . . . 111.4 no
    H301 C30 H303 . . . 107.1 no
    H302 C30 H303 . . . 110.3 no
    C19 C31 H311 . . . 109.0 no
    C19 C31 H312 . . . 109.6 no
    H311 C31 H312 . . . 108.8 no
    C19 C31 H313 . . . 109.2 no
    H311 C31 H313 . . . 110.3 no
    H312 C31 H313 . . . 109.9 no
    C15 C32 H323 . . . 109.1 no
    C15 C32 H322 . . . 112.2 no
    H323 C32 H322 . . . 108.1 no
    C15 C32 H321 . . . 109.6 no
    H323 C32 H321 . . . 108.5 no
    H322 C32 H321 . . . 109.3 no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C18 H181 O1 . . 1_445 1.00 2.60 3.563(3) 162 yes
    O11 H111 O1 . . . 0.87 1.78 2.551(3) 145 yes