# Electronic Supplementary Material (ESI) for Food & Function.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ao4e4i2
_database_code_depnum_ccdc_archive 'CCDC 2217170'
loop_
_audit_author_name
_audit_author_address
'yang yu'
;jinan university
China
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_audit_creation_date             2023-08-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
(3S,4S,5R,7R)-eremophila-3,4-epoxy-1(10),11-dien-2-one
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.12559(16)
_cell_length_b                   9.43073(17)
_cell_length_c                   14.8426(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1277.37(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7764
_cell_measurement_temperature    170.0(2)
_cell_measurement_theta_max      73.6070
_cell_measurement_theta_min      2.9330
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10532
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.863
_diffrn_reflns_theta_min         5.558
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00 -90.00   99
  2  ω    -69.00  32.00   1.00    1.00    --  -40.73  57.00  60.00  101
  3  ω    -96.00  -2.00   1.00    1.00    --  -40.73 125.00-180.00   94
  4  ω   -111.00 -16.00   1.00    1.00    --  -40.73 -57.00 150.00   95
  5  ω     26.00  86.00   1.00    1.00    --   40.73-125.00 -30.00   60
  6  ω    -20.00  62.00   1.00    1.00    --   40.73 -38.00 -30.00   82
  7  ω     65.00 109.00   1.00    1.22    --  107.58 -94.00-180.00   44
  8  ω     31.00 129.00   1.00    1.22    --  107.58 -77.00-120.00   98
  9  ω     36.00 125.00   1.00    1.22    --  107.58 -45.00  90.00   89
 10  ω     59.00  84.00   1.00    1.22    --  107.58 -94.00 150.00   25
 11  ω     40.00 122.00   1.00    1.22    --  107.58-125.00  60.00   82
 12  ω     81.00 173.00   1.00    1.22    --  107.58  30.00-180.00   92
 13  ω     38.00 115.00   1.00    1.22    --  107.58 -45.00   0.00   77
 14  ω    120.00 147.00   1.00    1.22    --  107.58 -15.00 150.00   27
 15  ω     33.00 116.00   1.00    1.22    --  107.58 -15.00 150.00   83
 16  ω     77.00 119.00   1.00    1.22    --  107.58-125.00 120.00   42
 17  ω     96.00 122.00   1.00    1.22    --  107.58 125.00-150.00   26
 18  ω    148.00 174.00   1.00    1.22    --  107.58 125.00-150.00   26
 19  ω     57.00 132.00   1.00    1.22    --  107.58 -30.00-150.00   75
 20  ω   -117.00  -8.00   1.00    2.00    --  -40.98 -77.00 -90.00  109
 21  ω   -117.00 -76.00   1.00    2.00    --  -40.98 -77.00   0.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1332872000
_diffrn_orient_matrix_UB_12      -0.1001243000
_diffrn_orient_matrix_UB_13      0.0022077000
_diffrn_orient_matrix_UB_21      -0.0941074000
_diffrn_orient_matrix_UB_22      0.1193252000
_diffrn_orient_matrix_UB_23      0.0409813000
_diffrn_orient_matrix_UB_31      -0.0434908000
_diffrn_orient_matrix_UB_32      0.0491129000
_diffrn_orient_matrix_UB_33      -0.0953277000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2451
_reflns_number_total             2551
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(14)
_refine_ls_extinction_coef       0.0053(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.037
_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/[σ²(Fo²)+(0.0513P)²+0.1162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0872
_refine_special_details          ?
_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:
 C7(H7), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O -0.18263(14) -0.54563(13) -0.20391(8) 0.0318(3) Uani 1 1 d . . . . .
C10 C -0.08651(18) -0.53658(17) -0.39840(11) 0.0264(4) Uani 1 1 d . . . . .
C6 C -0.11424(18) -0.27702(17) -0.39375(11) 0.0249(3) Uani 1 1 d . . . . .
H6A H -0.215869 -0.281077 -0.416948 0.030 Uiso 1 1 calc R U . . .
H6B H -0.105929 -0.191504 -0.355403 0.030 Uiso 1 1 calc R U . . .
C8 C -0.0078(2) -0.39737(18) -0.53054(12) 0.0306(4) Uani 1 1 d . . . . .
H8A H 0.067100 -0.389182 -0.578488 0.037 Uiso 1 1 calc R U . . .
H8B H -0.104538 -0.408678 -0.559905 0.037 Uiso 1 1 calc R U . . .
C7 C -0.00816(18) -0.26188(17) -0.47428(11) 0.0254(4) Uani 1 1 d . . . . .
H7 H 0.092660 -0.250335 -0.448914 0.030 Uiso 1 1 calc R U . . .
C5 C -0.08573(17) -0.41045(17) -0.33460(11) 0.0238(3) Uani 1 1 d . . . . .
C11 C -0.04229(18) -0.12862(19) -0.52778(11) 0.0278(4) Uani 1 1 d . . . . .
C4 C -0.20144(19) -0.42129(18) -0.26061(11) 0.0265(4) Uani 1 1 d . . . . .
O1 O -0.41022(16) -0.72964(16) -0.34119(10) 0.0487(4) Uani 1 1 d . . . . .
C2 C -0.3098(2) -0.64377(19) -0.33505(12) 0.0328(4) Uani 1 1 d . . . . .
C3 C -0.3101(2) -0.5372(2) -0.26147(12) 0.0304(4) Uani 1 1 d . . . . .
H3 H -0.406180 -0.518074 -0.231423 0.036 Uiso 1 1 calc R U . . .
C9 C 0.0245(2) -0.5288(2) -0.47317(13) 0.0330(4) Uani 1 1 d . . . . .
H9A H 0.018831 -0.615230 -0.510877 0.040 Uiso 1 1 calc R U . . .
H9B H 0.124550 -0.522470 -0.447631 0.040 Uiso 1 1 calc R U . . .
C13 C -0.0386(3) 0.00858(19) -0.47629(14) 0.0416(5) Uani 1 1 d . . . . .
H13A H -0.121532 0.011951 -0.434386 0.062 Uiso 1 1 calc R U . . .
H13B H -0.045249 0.088226 -0.518510 0.062 Uiso 1 1 calc R U . . .
H13C H 0.053319 0.015033 -0.442419 0.062 Uiso 1 1 calc R U . . .
C14 C -0.2393(2) -0.2898(2) -0.20767(14) 0.0365(4) Uani 1 1 d . . . . .
H14A H -0.302122 -0.315480 -0.156658 0.055 Uiso 1 1 calc R U . . .
H14B H -0.291308 -0.222758 -0.246714 0.055 Uiso 1 1 calc R U . . .
H14C H -0.149184 -0.245698 -0.185254 0.055 Uiso 1 1 calc R U . . .
C15 C 0.06371(18) -0.39816(19) -0.28671(12) 0.0302(4) Uani 1 1 d . . . . .
H15A H 0.081331 -0.483755 -0.250873 0.045 Uiso 1 1 calc R U . . .
H15B H 0.063282 -0.315069 -0.247061 0.045 Uiso 1 1 calc R U . . .
H15C H 0.141489 -0.387845 -0.331766 0.045 Uiso 1 1 calc R U . . .
C1 C -0.1877(2) -0.63945(18) -0.39753(12) 0.0316(4) Uani 1 1 d . . . . .
H1 H -0.179043 -0.713878 -0.440332 0.038 Uiso 1 1 calc R U . . .
C12 C -0.0717(2) -0.1289(2) -0.61513(12) 0.0337(4) Uani 1 1 d . . . . .
H12A H -0.092(2) -0.037(2) -0.6477(14) 0.040(6) Uiso 1 1 d . . . . .
H12B H -0.071(2) -0.216(3) -0.6491(15) 0.045(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O2 C4 1.454(2) . ?
O2 C3 1.445(2) . ?
C10 C5 1.520(2) . ?
C10 C9 1.505(2) . ?
C10 C1 1.340(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.545(2) . ?
C6 C5 1.556(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.526(2) . ?
C8 C9 1.533(2) . ?
C7 H7 1.0000 . ?
C7 C11 1.519(2) . ?
C5 C4 1.527(2) . ?
C5 C15 1.542(2) . ?
C11 C13 1.503(2) . ?
C11 C12 1.324(3) . ?
C4 C3 1.476(2) . ?
C4 C14 1.508(2) . ?
O1 C2 1.227(2) . ?
C2 C3 1.484(3) . ?
C2 C1 1.450(3) . ?
C3 H3 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1 H1 0.9500 . ?
C12 H12A 1.01(2) . ?
C12 H12B 0.97(2) . ?

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
C3 O2 C4 61.20(10) . . ?
C9 C10 C5 114.72(14) . . ?
C1 C10 C5 124.32(15) . . ?
C1 C10 C9 120.45(16) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C7 C6 C5 113.98(13) . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C7 C8 C9 111.93(14) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C6 C7 H7 107.2 . . ?
C8 C7 C6 110.31(13) . . ?
C8 C7 H7 107.2 . . ?
C11 C7 C6 110.64(13) . . ?
C11 C7 C8 114.02(13) . . ?
C11 C7 H7 107.2 . . ?
C10 C5 C6 106.29(12) . . ?
C10 C5 C4 113.10(13) . . ?
C10 C5 C15 110.49(13) . . ?
C4 C5 C6 110.14(13) . . ?
C4 C5 C15 106.56(13) . . ?
C15 C5 C6 110.31(13) . . ?
C13 C11 C7 116.23(14) . . ?
C12 C11 C7 123.51(16) . . ?
C12 C11 C13 120.25(17) . . ?
O2 C4 C5 112.88(13) . . ?
O2 C4 C3 59.13(10) . . ?
O2 C4 C14 112.88(14) . . ?
C3 C4 C5 120.54(15) . . ?
C3 C4 C14 117.34(15) . . ?
C14 C4 C5 118.57(14) . . ?
O1 C2 C3 120.01(17) . . ?
O1 C2 C1 123.04(17) . . ?
C1 C2 C3 116.95(15) . . ?
O2 C3 C4 59.67(10) . . ?
O2 C3 C2 113.31(15) . . ?
O2 C3 H3 116.9 . . ?
C4 C3 C2 120.42(15) . . ?
C4 C3 H3 116.9 . . ?
C2 C3 H3 116.9 . . ?
C10 C9 C8 108.62(14) . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
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 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C1 C2 123.79(16) . . ?
C10 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C11 C12 H12A 120.3(13) . . ?
C11 C12 H12B 120.7(13) . . ?
H12A C12 H12B 119.0(17) . . ?

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
O2 C4 C3 C2 -100.84(17) . . . . ?
C10 C5 C4 O2 60.09(17) . . . . ?
C10 C5 C4 C3 -6.5(2) . . . . ?
C10 C5 C4 C14 -164.66(15) . . . . ?
C6 C7 C11 C13 57.13(19) . . . . ?
C6 C7 C11 C12 -123.98(18) . . . . ?
C6 C5 C4 O2 178.86(12) . . . . ?
C6 C5 C4 C3 112.29(16) . . . . ?
C6 C5 C4 C14 -45.89(19) . . . . ?
C8 C7 C11 C13 -177.84(16) . . . . ?
C8 C7 C11 C12 1.0(2) . . . . ?
C7 C6 C5 C10 -53.58(17) . . . . ?
C7 C6 C5 C4 -176.43(13) . . . . ?
C7 C6 C5 C15 66.22(17) . . . . ?
C7 C8 C9 C10 56.65(19) . . . . ?
C5 C10 C9 C8 -60.85(18) . . . . ?
C5 C10 C1 C2 -0.2(3) . . . . ?
C5 C6 C7 C8 53.50(18) . . . . ?
C5 C6 C7 C11 -179.40(13) . . . . ?
C5 C4 C3 O2 99.98(16) . . . . ?
C5 C4 C3 C2 -0.9(2) . . . . ?
C4 O2 C3 C2 112.75(16) . . . . ?
O1 C2 C3 O2 121.13(18) . . . . ?
O1 C2 C3 C4 -171.49(17) . . . . ?
O1 C2 C1 C10 171.78(18) . . . . ?
C3 O2 C4 C5 -112.97(16) . . . . ?
C3 O2 C4 C14 109.18(17) . . . . ?
C3 C2 C1 C10 -7.8(3) . . . . ?
C9 C10 C5 C6 58.15(17) . . . . ?
C9 C10 C5 C4 179.12(14) . . . . ?
C9 C10 C5 C15 -61.53(18) . . . . ?
C9 C10 C1 C2 -171.55(16) . . . . ?
C9 C8 C7 C6 -53.83(19) . . . . ?
C9 C8 C7 C11 -179.02(14) . . . . ?
C14 C4 C3 O2 -101.58(16) . . . . ?
C14 C4 C3 C2 157.58(16) . . . . ?
C15 C5 C4 O2 -61.49(16) . . . . ?
C15 C5 C4 C3 -128.06(16) . . . . ?
C15 C5 C4 C14 73.76(18) . . . . ?
C1 C10 C5 C6 -113.62(17) . . . . ?
C1 C10 C5 C4 7.4(2) . . . . ?
C1 C10 C5 C15 126.70(18) . . . . ?
C1 C10 C9 C8 111.27(19) . . . . ?
C1 C2 C3 O2 -59.3(2) . . . . ?
C1 C2 C3 C4 8.1(2) . . . . ?

_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 1.577
_oxdiff_exptl_absorpt_empirical_full_min 0.686
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_f5e1-2
_database_code_depnum_ccdc_archive 'CCDC 2221275'
loop_
_audit_author_name
_audit_author_address
'yang yu'
;jinan university
China
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_audit_creation_date             2023-08-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
(2R,4R,5S,7S,9R)-eremophila-1(10),11-dien-2,9-diol
_chemical_formula_moiety         '3(C15 H24 O2), C H4 O'
_chemical_formula_sum            'C46 H76 O7'
_chemical_formula_weight         741.06
_chemical_absolute_configuration UNKNOWN
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.1552(6)
_cell_length_b                   20.429(2)
_cell_length_c                   27.192(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4530.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7890
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      99
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.1223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12357
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.687
_diffrn_reflns_theta_min         2.705
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.576
_reflns_Friedel_fraction_full    0.769
_reflns_Friedel_fraction_max     0.714
_reflns_number_gt                5210
_reflns_number_total             7861
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1237 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       0.00109(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         7861
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      1.005
_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/[σ²(Fo²)+(0.0647P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1909
_refine_special_details          ?
_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. Restrained distances
 O1M-H1M
 0.96 with sigma of 0.02
 O1A_$1-H1A_$1
 0.96 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2A(H2AA), C4A(H4A), C7A(H7A), C9A(H9A), C2B(H2BA), C4B(H4B), C7B(H7B),
 C9B(H9B), C2C(H2CA), C4C(H4C), C7C(H7C), C9C(H9C)
3.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C6A(H6AA,H6AB), C8A(H8AA,H8AB), C3B(H3BA,H3BB), C6B(H6BA,
 H6BB), C8B(H8BA,H8BB), C3C(H3CA,H3CB), C6C(H6CA,H6CB), C8C(H8CA,H8CB)
3.c Aromatic/amide H refined with riding coordinates:
 C1A(H1AA), C1B(H1BA), C1C(H1CA)
3.d X=CH2 refined with riding coordinates:
 C12A(H12A,H12B), C12B(H12C,H12D), C12C(H12E,H12F)
3.e Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C15A(H15A,H15B,H15C), C13B(H13D,
 H13E,H13F), C14B(H14D,H14E,H14F), C15B(H15D,H15E,H15F), C13C(H13G,H13H,H13I),
 C14C(H14G,H14H,H14I), C15C(H15G,H15H,H15I), C1M(H1MA,H1MB,H1MC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1A O 0.0291(4) 0.5740(2) 0.80002(18) 0.0400(10) Uani 1 1 d . . . . .
O2A O 0.7160(4) 0.5347(2) 0.81589(16) 0.0339(9) Uani 1 1 d . . . . .
C1A C 0.3125(6) 0.5504(3) 0.7960(2) 0.0307(12) Uani 1 1 d . . . . .
H1AA H 0.339616 0.565887 0.764078 0.037 Uiso 1 1 calc R U . . .
C2A C 0.1459(6) 0.5212(3) 0.8038(2) 0.0316(12) Uani 1 1 d . . . . .
H2AA H 0.123789 0.488872 0.776975 0.038 Uiso 1 1 calc R U . . .
C3A C 0.1325(7) 0.4867(3) 0.8530(2) 0.0357(13) Uani 1 1 d . . . . .
H3AA H 0.187174 0.443561 0.850986 0.043 Uiso 1 1 calc R U . . .
H3AB H 0.015461 0.479262 0.860884 0.043 Uiso 1 1 calc R U . . .
C4A C 0.2111(7) 0.5269(3) 0.8940(2) 0.0356(13) Uani 1 1 d . . . . .
H4A H 0.160183 0.571390 0.892787 0.043 Uiso 1 1 calc R U . . .
C5A C 0.3980(7) 0.5363(3) 0.8853(2) 0.0322(12) Uani 1 1 d . . . . .
C6A C 0.4603(7) 0.5919(3) 0.9186(2) 0.0355(13) Uani 1 1 d . . . . .
H6AA H 0.388208 0.630511 0.914401 0.043 Uiso 1 1 calc R U . . .
H6AB H 0.452032 0.577721 0.953363 0.043 Uiso 1 1 calc R U . . .
C7A C 0.6370(7) 0.6121(3) 0.9080(2) 0.0346(13) Uani 1 1 d . . . . .
H7A H 0.706278 0.571887 0.910875 0.042 Uiso 1 1 calc R U . . .
C8A C 0.6489(7) 0.6357(3) 0.8549(2) 0.0327(12) Uani 1 1 d . . . . .
H8AA H 0.581357 0.675632 0.850988 0.039 Uiso 1 1 calc R U . . .
H8AB H 0.764142 0.647529 0.847628 0.039 Uiso 1 1 calc R U . . .
C9A C 0.5919(6) 0.5844(3) 0.8180(2) 0.0282(12) Uani 1 1 d . . . . .
H9A H 0.582453 0.605336 0.784935 0.034 Uiso 1 1 calc R U . . .
C10A C 0.4264(5) 0.5559(3) 0.83196(19) 0.0233(10) Uani 1 1 d . . . . .
C11A C 0.7050(9) 0.6621(3) 0.9439(3) 0.0443(16) Uani 1 1 d . . . . .
C12A C 0.6124(12) 0.7049(5) 0.9680(4) 0.090(4) Uani 1 1 d . . . . .
H12A H 0.662172 0.736618 0.988793 0.108 Uiso 1 1 calc R U . . .
H12B H 0.496571 0.703854 0.964521 0.108 Uiso 1 1 calc R U . . .
C13A C 0.8862(10) 0.6627(5) 0.9488(4) 0.073(3) Uani 1 1 d . . . . .
H13A H 0.919471 0.699868 0.969250 0.110 Uiso 1 1 calc R U . . .
H13B H 0.936040 0.666864 0.916107 0.110 Uiso 1 1 calc R U . . .
H13C H 0.922743 0.621844 0.964104 0.110 Uiso 1 1 calc R U . . .
C14A C 0.1681(9) 0.4975(4) 0.9442(3) 0.056(2) Uani 1 1 d . . . . .
H14A H 0.048691 0.494921 0.947585 0.085 Uiso 1 1 calc R U . . .
H14B H 0.212931 0.525325 0.970292 0.085 Uiso 1 1 calc R U . . .
H14C H 0.215279 0.453535 0.946753 0.085 Uiso 1 1 calc R U . . .
C15A C 0.4911(7) 0.4735(3) 0.8971(2) 0.0366(13) Uani 1 1 d . . . . .
H15A H 0.485383 0.464921 0.932550 0.055 Uiso 1 1 calc R U . . .
H15B H 0.606055 0.478286 0.887239 0.055 Uiso 1 1 calc R U . . .
H15C H 0.441777 0.436797 0.879200 0.055 Uiso 1 1 calc R U . . .
O1B O 0.6608(6) 0.4708(2) 0.73033(16) 0.0401(10) Uani 1 1 d . . . . .
O2B O 0.8704(5) 0.2307(2) 0.81596(18) 0.0371(10) Uani 1 1 d . . . . .
C1B C 0.7867(7) 0.3722(3) 0.7533(2) 0.0325(12) Uani 1 1 d . . . . .
H1BA H 0.897792 0.384491 0.758211 0.039 Uiso 1 1 calc R U . . .
C2B C 0.6937(7) 0.4054(3) 0.7134(2) 0.0323(12) Uani 1 1 d . . . . .
H2BA H 0.764775 0.407915 0.683516 0.039 Uiso 1 1 calc R U . . .
C3B C 0.5388(7) 0.3692(3) 0.7004(2) 0.0360(13) Uani 1 1 d . . . . .
H3BA H 0.566320 0.329363 0.681404 0.043 Uiso 1 1 calc R U . . .
H3BB H 0.468131 0.397329 0.679720 0.043 Uiso 1 1 calc R U . . .
C4B C 0.4472(6) 0.3501(3) 0.7470(2) 0.0327(13) Uani 1 1 d . . . . .
H4B H 0.435141 0.391181 0.766724 0.039 Uiso 1 1 calc R U . . .
C5B C 0.5464(6) 0.3019(3) 0.7794(2) 0.0269(11) Uani 1 1 d . . . . .
C6B C 0.4711(6) 0.3020(3) 0.8313(2) 0.0296(12) Uani 1 1 d . . . . .
H6BA H 0.446390 0.347836 0.840365 0.036 Uiso 1 1 calc R U . . .
H6BB H 0.365463 0.278177 0.829835 0.036 Uiso 1 1 calc R U . . .
C7B C 0.5735(6) 0.2721(3) 0.8722(2) 0.0290(12) Uani 1 1 d . . . . .
H7B H 0.587738 0.224563 0.864359 0.035 Uiso 1 1 calc R U . . .
C8B C 0.7448(6) 0.3030(3) 0.8733(2) 0.0345(13) Uani 1 1 d . . . . .
H8BA H 0.735271 0.349595 0.882869 0.041 Uiso 1 1 calc R U . . .
H8BB H 0.812494 0.280539 0.898331 0.041 Uiso 1 1 calc R U . . .
C9B C 0.8298(6) 0.2984(3) 0.8235(2) 0.0310(12) Uani 1 1 d . . . . .
H9B H 0.933767 0.324260 0.824891 0.037 Uiso 1 1 calc R U . . .
C10B C 0.7236(6) 0.3258(3) 0.7828(2) 0.0288(11) Uani 1 1 d . . . . .
C11B C 0.4909(7) 0.2764(3) 0.9224(2) 0.0341(13) Uani 1 1 d . . . . .
C12B C 0.3462(8) 0.3032(3) 0.9300(3) 0.0452(15) Uani 1 1 d . . . . .
H12C H 0.301093 0.304182 0.962202 0.054 Uiso 1 1 calc R U . . .
H12D H 0.287020 0.321664 0.903284 0.054 Uiso 1 1 calc R U . . .
C13B C 0.5861(9) 0.2469(4) 0.9648(2) 0.0472(16) Uani 1 1 d . . . . .
H13D H 0.633935 0.205127 0.954468 0.071 Uiso 1 1 calc R U . . .
H13E H 0.512070 0.239622 0.992629 0.071 Uiso 1 1 calc R U . . .
H13F H 0.673765 0.276985 0.974629 0.071 Uiso 1 1 calc R U . . .
C14B C 0.2722(7) 0.3274(4) 0.7347(3) 0.0492(18) Uani 1 1 d . . . . .
H14D H 0.211164 0.363579 0.719704 0.074 Uiso 1 1 calc R U . . .
H14E H 0.216700 0.313392 0.764862 0.074 Uiso 1 1 calc R U . . .
H14F H 0.277150 0.290608 0.711551 0.074 Uiso 1 1 calc R U . . .
C15B C 0.5400(7) 0.2324(3) 0.7575(2) 0.0329(12) Uani 1 1 d . . . . .
H15D H 0.425670 0.217988 0.755196 0.049 Uiso 1 1 calc R U . . .
H15E H 0.601247 0.202285 0.778683 0.049 Uiso 1 1 calc R U . . .
H15F H 0.589139 0.232718 0.724575 0.049 Uiso 1 1 calc R U . . .
O1C O 0.5526(4) 0.5673(2) 0.66909(17) 0.0393(10) Uani 1 1 d . . . . .
O2C O 1.2378(4) 0.6075(2) 0.65282(16) 0.0313(9) Uani 1 1 d . . . . .
C1C C 0.8301(6) 0.5984(3) 0.6680(2) 0.0286(11) Uani 1 1 d . . . . .
H1CA H 0.850535 0.605357 0.701980 0.034 Uiso 1 1 calc R U . . .
C2C C 0.6627(6) 0.6143(3) 0.6484(2) 0.0304(12) Uani 1 1 d . . . . .
H2CA H 0.630713 0.658819 0.660256 0.036 Uiso 1 1 calc R U . . .
C3C C 0.6598(6) 0.6142(3) 0.5927(2) 0.0362(13) Uani 1 1 d . . . . .
H3CA H 0.709293 0.655256 0.580390 0.043 Uiso 1 1 calc R U . . .
H3CB H 0.544667 0.612548 0.581218 0.043 Uiso 1 1 calc R U . . .
C4C C 0.7536(6) 0.5558(3) 0.5716(2) 0.0341(13) Uani 1 1 d . . . . .
H4C H 0.708856 0.515490 0.587551 0.041 Uiso 1 1 calc R U . . .
C5C C 0.9396(6) 0.5604(3) 0.5857(2) 0.0276(11) Uani 1 1 d . . . . .
C6C C 1.0163(6) 0.4918(3) 0.5757(2) 0.0322(12) Uani 1 1 d . . . . .
H6CA H 0.942152 0.457874 0.589192 0.039 Uiso 1 1 calc R U . . .
H6CB H 1.022974 0.485065 0.539726 0.039 Uiso 1 1 calc R U . . .
C7C C 1.1874(6) 0.4819(3) 0.5978(2) 0.0316(12) Uani 1 1 d . . . . .
H7C H 1.262339 0.515606 0.583429 0.038 Uiso 1 1 calc R U . . .
C8C C 1.1776(6) 0.4933(3) 0.6535(2) 0.0311(12) Uani 1 1 d . . . . .
H8CA H 1.104797 0.459955 0.668336 0.037 Uiso 1 1 calc R U . . .
H8CB H 1.288149 0.487906 0.667997 0.037 Uiso 1 1 calc R U . . .
C9C C 1.1130(5) 0.5611(3) 0.6661(2) 0.0270(11) Uani 1 1 d . . . . .
H9C H 1.094799 0.563620 0.702391 0.032 Uiso 1 1 calc R U . . .
C10C C 0.9520(6) 0.5749(3) 0.64026(18) 0.0244(11) Uani 1 1 d . . . . .
C11C C 1.2561(7) 0.4149(3) 0.5860(2) 0.0388(14) Uani 1 1 d . . . . .
C12C C 1.4104(8) 0.4086(4) 0.5692(3) 0.0510(18) Uani 1 1 d . . . . .
H12E H 1.454128 0.366278 0.562946 0.061 Uiso 1 1 calc R U . . .
H12F H 1.475676 0.446356 0.563589 0.061 Uiso 1 1 calc R U . . .
C13C C 1.1503(10) 0.3563(3) 0.5952(3) 0.059(2) Uani 1 1 d . . . . .
H13G H 1.099592 0.359966 0.627755 0.088 Uiso 1 1 calc R U . . .
H13H H 1.217531 0.316611 0.593820 0.088 Uiso 1 1 calc R U . . .
H13I H 1.064469 0.354027 0.570025 0.088 Uiso 1 1 calc R U . . .
C14C C 0.7223(8) 0.5494(4) 0.5164(2) 0.055(2) Uani 1 1 d . . . . .
H14G H 0.604492 0.544154 0.510502 0.082 Uiso 1 1 calc R U . . .
H14H H 0.780913 0.511083 0.503660 0.082 Uiso 1 1 calc R U . . .
H14I H 0.761485 0.588843 0.499569 0.082 Uiso 1 1 calc R U . . .
C15C C 1.0279(7) 0.6130(3) 0.5561(2) 0.0368(14) Uani 1 1 d . . . . .
H15G H 1.013747 0.604344 0.520885 0.055 Uiso 1 1 calc R U . . .
H15H H 1.144997 0.612511 0.564204 0.055 Uiso 1 1 calc R U . . .
H15I H 0.981791 0.656006 0.564074 0.055 Uiso 1 1 calc R U . . .
O1M O 0.0368(7) 0.7017(3) 0.7782(2) 0.0561(13) Uani 1 1 d D . . . .
C1M C 0.0799(11) 0.7334(5) 0.8237(4) 0.075(3) Uani 1 1 d . . . . .
H1MA H 0.088722 0.780729 0.818364 0.112 Uiso 1 1 calc R U . . .
H1MB H 0.185304 0.716422 0.835406 0.112 Uiso 1 1 calc R U . . .
H1MC H -0.004991 0.724676 0.848369 0.112 Uiso 1 1 calc R U . . .
H1C H 0.439(10) 0.584(4) 0.665(3) 0.06(2) Uiso 1 1 d . . . . .
H1A H -0.080(5) 0.557(4) 0.806(4) 0.09(3) Uiso 1 1 d . . . . .
H2A H 0.695(13) 0.502(5) 0.794(4) 0.10(4) Uiso 1 1 d . . . . .
H2C H 1.199(13) 0.648(5) 0.661(4) 0.10(4) Uiso 1 1 d . . . . .
H1B H 0.614(15) 0.509(6) 0.710(5) 0.15(5) Uiso 1 1 d . . . . .
H2B H 0.901(12) 0.219(5) 0.780(4) 0.10(4) Uiso 1 1 d . . . . .
H1M H 0.059(15) 0.656(2) 0.784(5) 0.14(5) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1A C2A 1.443(7) . ?
O1A H1A 0.97(3) . ?
O2A C9A 1.435(6) . ?
O2A H2A 0.91(11) . ?
C1A H1AA 0.9500 . ?
C1A C2A 1.498(7) . ?
C1A C10A 1.353(7) . ?
C2A H2AA 1.0000 . ?
C2A C3A 1.517(8) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.525(9) . ?
C4A H4A 1.0000 . ?
C4A C5A 1.554(8) . ?
C4A C14A 1.531(8) . ?
C5A C6A 1.540(8) . ?
C5A C10A 1.522(8) . ?
C5A C15A 1.526(8) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.527(8) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.526(8) . ?
C7A C11A 1.517(9) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.524(8) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.518(7) . ?
C11A C12A 1.329(10) . ?
C11A C13A 1.484(11) . ?
C12A H12A 0.9500 . ?
C12A H12B 0.9500 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
O1B C2B 1.438(7) . ?
O1B H1B 1.03(13) . ?
O2B C9B 1.437(7) . ?
O2B H2B 1.04(11) . ?
C1B H1BA 0.9500 . ?
C1B C2B 1.487(8) . ?
C1B C10B 1.344(8) . ?
C2B H2BA 1.0000 . ?
C2B C3B 1.506(8) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.521(8) . ?
C4B H4B 1.0000 . ?
C4B C5B 1.550(7) . ?
C4B C14B 1.538(8) . ?
C5B C6B 1.539(7) . ?
C5B C10B 1.528(7) . ?
C5B C15B 1.541(8) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C6B C7B 1.519(7) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.534(7) . ?
C7B C11B 1.525(8) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.524(8) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.512(8) . ?
C11B C12B 1.317(9) . ?
C11B C13B 1.514(8) . ?
C12B H12C 0.9500 . ?
C12B H12D 0.9500 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
O1C C2C 1.430(7) . ?
O1C H1C 0.99(8) . ?
O2C C9C 1.436(6) . ?
O2C H2C 0.91(10) . ?
C1C H1CA 0.9500 . ?
C1C C2C 1.501(7) . ?
C1C C10C 1.337(7) . ?
C2C H2CA 1.0000 . ?
C2C C3C 1.515(8) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?
C3C C4C 1.529(8) . ?
C4C H4C 1.0000 . ?
C4C C5C 1.568(7) . ?
C4C C14C 1.528(8) . ?
C5C C6C 1.558(8) . ?
C5C C10C 1.515(7) . ?
C5C C15C 1.525(8) . ?
C6C H6CA 0.9900 . ?
C6C H6CB 0.9900 . ?
C6C C7C 1.532(7) . ?
C7C H7C 1.0000 . ?
C7C C8C 1.535(8) . ?
C7C C11C 1.513(8) . ?
C8C H8CA 0.9900 . ?
C8C H8CB 0.9900 . ?
C8C C9C 1.521(8) . ?
C9C H9C 1.0000 . ?
C9C C10C 1.515(7) . ?
C11C C12C 1.345(9) . ?
C11C C13C 1.497(10) . ?
C12C H12E 0.9500 . ?
C12C H12F 0.9500 . ?
C13C H13G 0.9800 . ?
C13C H13H 0.9800 . ?
C13C H13I 0.9800 . ?
C14C H14G 0.9800 . ?
C14C H14H 0.9800 . ?
C14C H14I 0.9800 . ?
C15C H15G 0.9800 . ?
C15C H15H 0.9800 . ?
C15C H15I 0.9800 . ?
O1M C1M 1.441(11) . ?
O1M H1M 0.97(3) . ?
C1M H1MA 0.9800 . ?
C1M H1MB 0.9800 . ?
C1M H1MC 0.9800 . ?

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
C2A O1A H1A 110(6) . . ?
C9A O2A H2A 115(7) . . ?
C2A C1A H1AA 118.2 . . ?
C10A C1A H1AA 118.2 . . ?
C10A C1A C2A 123.6(5) . . ?
O1A C2A C1A 106.9(5) . . ?
O1A C2A H2AA 108.9 . . ?
O1A C2A C3A 111.2(5) . . ?
C1A C2A H2AA 108.9 . . ?
C1A C2A C3A 112.0(5) . . ?
C3A C2A H2AA 108.9 . . ?
C2A C3A H3AA 109.3 . . ?
C2A C3A H3AB 109.3 . . ?
C2A C3A C4A 111.4(5) . . ?
H3AA C3A H3AB 108.0 . . ?
C4A C3A H3AA 109.3 . . ?
C4A C3A H3AB 109.3 . . ?
C3A C4A H4A 106.9 . . ?
C3A C4A C5A 111.6(5) . . ?
C3A C4A C14A 110.1(5) . . ?
C5A C4A H4A 106.9 . . ?
C14A C4A H4A 106.9 . . ?
C14A C4A C5A 114.1(5) . . ?
C6A C5A C4A 108.9(5) . . ?
C10A C5A C4A 109.1(5) . . ?
C10A C5A C6A 108.5(5) . . ?
C10A C5A C15A 110.3(5) . . ?
C15A C5A C4A 110.6(5) . . ?
C15A C5A C6A 109.4(5) . . ?
C5A C6A H6AA 108.9 . . ?
C5A C6A H6AB 108.9 . . ?
H6AA C6A H6AB 107.7 . . ?
C7A C6A C5A 113.5(5) . . ?
C7A C6A H6AA 108.9 . . ?
C7A C6A H6AB 108.9 . . ?
C6A C7A H7A 107.3 . . ?
C8A C7A C6A 108.9(5) . . ?
C8A C7A H7A 107.3 . . ?
C11A C7A C6A 113.9(5) . . ?
C11A C7A H7A 107.3 . . ?
C11A C7A C8A 111.9(5) . . ?
C7A C8A H8AA 109.1 . . ?
C7A C8A H8AB 109.1 . . ?
H8AA C8A H8AB 107.8 . . ?
C9A C8A C7A 112.7(5) . . ?
C9A C8A H8AA 109.1 . . ?
C9A C8A H8AB 109.1 . . ?
O2A C9A C8A 107.4(4) . . ?
O2A C9A H9A 108.7 . . ?
O2A C9A C10A 111.5(5) . . ?
C8A C9A H9A 108.7 . . ?
C10A C9A C8A 111.8(4) . . ?
C10A C9A H9A 108.7 . . ?
C1A C10A C5A 124.2(5) . . ?
C1A C10A C9A 117.5(5) . . ?
C9A C10A C5A 118.3(4) . . ?
C12A C11A C7A 123.6(7) . . ?
C12A C11A C13A 121.0(8) . . ?
C13A C11A C7A 115.3(7) . . ?
C11A C12A H12A 120.0 . . ?
C11A C12A H12B 120.0 . . ?
H12A C12A H12B 120.0 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C4A C14A H14A 109.5 . . ?
C4A C14A H14B 109.5 . . ?
C4A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C5A C15A H15A 109.5 . . ?
C5A C15A H15B 109.5 . . ?
C5A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C2B O1B H1B 127(7) . . ?
C9B O2B H2B 114(6) . . ?
C2B C1B H1BA 117.9 . . ?
C10B C1B H1BA 117.9 . . ?
C10B C1B C2B 124.2(5) . . ?
O1B C2B C1B 106.6(5) . . ?
O1B C2B H2BA 108.7 . . ?
O1B C2B C3B 112.0(5) . . ?
C1B C2B H2BA 108.7 . . ?
C1B C2B C3B 112.0(5) . . ?
C3B C2B H2BA 108.7 . . ?
C2B C3B H3BA 109.7 . . ?
C2B C3B H3BB 109.7 . . ?
C2B C3B C4B 110.0(5) . . ?
H3BA C3B H3BB 108.2 . . ?
C4B C3B H3BA 109.7 . . ?
C4B C3B H3BB 109.7 . . ?
C3B C4B H4B 106.2 . . ?
C3B C4B C5B 112.3(5) . . ?
C3B C4B C14B 110.6(5) . . ?
C5B C4B H4B 106.2 . . ?
C14B C4B H4B 106.2 . . ?
C14B C4B C5B 114.6(5) . . ?
C6B C5B C4B 108.2(4) . . ?
C6B C5B C15B 110.0(5) . . ?
C10B C5B C4B 109.0(5) . . ?
C10B C5B C6B 108.7(5) . . ?
C10B C5B C15B 110.5(4) . . ?
C15B C5B C4B 110.4(5) . . ?
C5B C6B H6BA 108.1 . . ?
C5B C6B H6BB 108.1 . . ?
H6BA C6B H6BB 107.3 . . ?
C7B C6B C5B 116.9(4) . . ?
C7B C6B H6BA 108.1 . . ?
C7B C6B H6BB 108.1 . . ?
C6B C7B H7B 107.4 . . ?
C6B C7B C8B 110.4(5) . . ?
C6B C7B C11B 112.9(5) . . ?
C8B C7B H7B 107.4 . . ?
C11B C7B H7B 107.4 . . ?
C11B C7B C8B 111.2(5) . . ?
C7B C8B H8BA 109.3 . . ?
C7B C8B H8BB 109.3 . . ?
H8BA C8B H8BB 107.9 . . ?
C9B C8B C7B 111.8(5) . . ?
C9B C8B H8BA 109.3 . . ?
C9B C8B H8BB 109.3 . . ?
O2B C9B C8B 106.9(5) . . ?
O2B C9B H9B 108.6 . . ?
O2B C9B C10B 112.7(5) . . ?
C8B C9B H9B 108.6 . . ?
C10B C9B C8B 111.5(4) . . ?
C10B C9B H9B 108.6 . . ?
C1B C10B C5B 123.4(5) . . ?
C1B C10B C9B 118.6(5) . . ?
C9B C10B C5B 117.9(5) . . ?
C12B C11B C7B 124.1(6) . . ?
C12B C11B C13B 120.3(6) . . ?
C13B C11B C7B 115.6(5) . . ?
C11B C12B H12C 120.0 . . ?
C11B C12B H12D 120.0 . . ?
H12C C12B H12D 120.0 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C4B C14B H14D 109.5 . . ?
C4B C14B H14E 109.5 . . ?
C4B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C5B C15B H15D 109.5 . . ?
C5B C15B H15E 109.5 . . ?
C5B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C2C O1C H1C 108(5) . . ?
C9C O2C H2C 107(7) . . ?
C2C C1C H1CA 118.2 . . ?
C10C C1C H1CA 118.2 . . ?
C10C C1C C2C 123.6(5) . . ?
O1C C2C C1C 106.6(5) . . ?
O1C C2C H2CA 108.7 . . ?
O1C C2C C3C 112.5(5) . . ?
C1C C2C H2CA 108.7 . . ?
C1C C2C C3C 111.6(5) . . ?
C3C C2C H2CA 108.7 . . ?
C2C C3C H3CA 109.3 . . ?
C2C C3C H3CB 109.3 . . ?
C2C C3C C4C 111.7(5) . . ?
H3CA C3C H3CB 107.9 . . ?
C4C C3C H3CA 109.3 . . ?
C4C C3C H3CB 109.3 . . ?
C3C C4C H4C 107.2 . . ?
C3C C4C C5C 110.2(5) . . ?
C5C C4C H4C 107.2 . . ?
C14C C4C C3C 110.6(5) . . ?
C14C C4C H4C 107.2 . . ?
C14C C4C C5C 114.1(5) . . ?
C6C C5C C4C 106.9(5) . . ?
C10C C5C C4C 108.5(4) . . ?
C10C C5C C6C 108.7(5) . . ?
C10C C5C C15C 110.4(5) . . ?
C15C C5C C4C 111.7(5) . . ?
C15C C5C C6C 110.6(5) . . ?
C5C C6C H6CA 108.6 . . ?
C5C C6C H6CB 108.6 . . ?
H6CA C6C H6CB 107.6 . . ?
C7C C6C C5C 114.5(5) . . ?
C7C C6C H6CA 108.6 . . ?
C7C C6C H6CB 108.6 . . ?
C6C C7C H7C 108.2 . . ?
C6C C7C C8C 108.6(4) . . ?
C8C C7C H7C 108.2 . . ?
C11C C7C C6C 111.9(5) . . ?
C11C C7C H7C 108.2 . . ?
C11C C7C C8C 111.5(5) . . ?
C7C C8C H8CA 109.2 . . ?
C7C C8C H8CB 109.2 . . ?
H8CA C8C H8CB 107.9 . . ?
C9C C8C C7C 112.2(5) . . ?
C9C C8C H8CA 109.2 . . ?
C9C C8C H8CB 109.2 . . ?
O2C C9C C8C 107.4(4) . . ?
O2C C9C H9C 108.6 . . ?
O2C C9C C10C 112.1(5) . . ?
C8C C9C H9C 108.6 . . ?
C10C C9C C8C 111.4(5) . . ?
C10C C9C H9C 108.6 . . ?
C1C C10C C5C 124.9(5) . . ?
C1C C10C C9C 116.7(5) . . ?
C9C C10C C5C 118.4(4) . . ?
C12C C11C C7C 120.4(6) . . ?
C12C C11C C13C 121.2(7) . . ?
C13C C11C C7C 118.3(5) . . ?
C11C C12C H12E 120.0 . . ?
C11C C12C H12F 120.0 . . ?
H12E C12C H12F 120.0 . . ?
C11C C13C H13G 109.5 . . ?
C11C C13C H13H 109.5 . . ?
C11C C13C H13I 109.5 . . ?
H13G C13C H13H 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
C4C C14C H14G 109.5 . . ?
C4C C14C H14H 109.5 . . ?
C4C C14C H14I 109.5 . . ?
H14G C14C H14H 109.5 . . ?
H14G C14C H14I 109.5 . . ?
H14H C14C H14I 109.5 . . ?
C5C C15C H15G 109.5 . . ?
C5C C15C H15H 109.5 . . ?
C5C C15C H15I 109.5 . . ?
H15G C15C H15H 109.5 . . ?
H15G C15C H15I 109.5 . . ?
H15H C15C H15I 109.5 . . ?
C1M O1M H1M 104(8) . . ?
O1M C1M H1MA 109.5 . . ?
O1M C1M H1MB 109.5 . . ?
O1M C1M H1MC 109.5 . . ?
H1MA C1M H1MB 109.5 . . ?
H1MA C1M H1MC 109.5 . . ?
H1MB C1M H1MC 109.5 . . ?

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
O1A C2A C3A C4A -76.3(6) . . . . ?
O2A C9A C10A C1A -105.9(6) . . . . ?
O2A C9A C10A C5A 74.9(6) . . . . ?
C1A C2A C3A C4A 43.2(7) . . . . ?
C2A C1A C10A C5A -3.0(9) . . . . ?
C2A C1A C10A C9A 177.9(5) . . . . ?
C2A C3A C4A C5A -62.7(6) . . . . ?
C2A C3A C4A C14A 169.5(5) . . . . ?
C3A C4A C5A C6A 164.2(5) . . . . ?
C3A C4A C5A C10A 46.0(7) . . . . ?
C3A C4A C5A C15A -75.5(6) . . . . ?
C4A C5A C6A C7A -171.8(5) . . . . ?
C4A C5A C10A C1A -14.5(8) . . . . ?
C4A C5A C10A C9A 164.6(5) . . . . ?
C5A C6A C7A C8A 60.1(7) . . . . ?
C5A C6A C7A C11A -174.3(5) . . . . ?
C6A C5A C10A C1A -133.0(6) . . . . ?
C6A C5A C10A C9A 46.1(7) . . . . ?
C6A C7A C8A C9A -57.0(6) . . . . ?
C6A C7A C11A C12A -27.4(11) . . . . ?
C6A C7A C11A C13A 155.6(7) . . . . ?
C7A C8A C9A O2A -73.2(6) . . . . ?
C7A C8A C9A C10A 49.4(6) . . . . ?
C8A C7A C11A C12A 96.6(10) . . . . ?
C8A C7A C11A C13A -80.3(8) . . . . ?
C8A C9A C10A C1A 133.8(6) . . . . ?
C8A C9A C10A C5A -45.3(7) . . . . ?
C10A C1A C2A O1A 110.6(6) . . . . ?
C10A C1A C2A C3A -11.4(8) . . . . ?
C10A C5A C6A C7A -53.2(6) . . . . ?
C11A C7A C8A C9A 176.2(5) . . . . ?
C14A C4A C5A C6A -70.2(7) . . . . ?
C14A C4A C5A C10A 171.6(5) . . . . ?
C14A C4A C5A C15A 50.1(8) . . . . ?
C15A C5A C6A C7A 67.2(6) . . . . ?
C15A C5A C10A C1A 107.2(6) . . . . ?
C15A C5A C10A C9A -73.7(6) . . . . ?
O1B C2B C3B C4B -73.4(6) . . . . ?
O2B C9B C10B C1B -113.3(6) . . . . ?
O2B C9B C10B C5B 70.0(6) . . . . ?
C1B C2B C3B C4B 46.3(7) . . . . ?
C2B C1B C10B C5B -0.7(9) . . . . ?
C2B C1B C10B C9B -177.2(5) . . . . ?
C2B C3B C4B C5B -63.4(7) . . . . ?
C2B C3B C4B C14B 167.2(5) . . . . ?
C3B C4B C5B C6B 163.1(5) . . . . ?
C3B C4B C5B C10B 45.0(7) . . . . ?
C3B C4B C5B C15B -76.5(6) . . . . ?
C4B C5B C6B C7B -164.8(5) . . . . ?
C4B C5B C10B C1B -13.7(8) . . . . ?
C4B C5B C10B C9B 162.8(5) . . . . ?
C5B C6B C7B C8B 53.0(7) . . . . ?
C5B C6B C7B C11B 178.1(5) . . . . ?
C6B C5B C10B C1B -131.5(6) . . . . ?
C6B C5B C10B C9B 45.0(7) . . . . ?
C6B C7B C8B C9B -54.5(7) . . . . ?
C6B C7B C11B C12B -0.1(9) . . . . ?
C6B C7B C11B C13B 179.5(5) . . . . ?
C7B C8B C9B O2B -70.4(6) . . . . ?
C7B C8B C9B C10B 53.1(7) . . . . ?
C8B C7B C11B C12B 124.6(6) . . . . ?
C8B C7B C11B C13B -55.7(7) . . . . ?
C8B C9B C10B C1B 126.5(6) . . . . ?
C8B C9B C10B C5B -50.2(7) . . . . ?
C10B C1B C2B O1B 106.9(7) . . . . ?
C10B C1B C2B C3B -15.9(8) . . . . ?
C10B C5B C6B C7B -46.6(7) . . . . ?
C11B C7B C8B C9B 179.4(5) . . . . ?
C14B C4B C5B C6B -69.7(7) . . . . ?
C14B C4B C5B C10B 172.2(5) . . . . ?
C14B C4B C5B C15B 50.7(7) . . . . ?
C15B C5B C6B C7B 74.6(6) . . . . ?
C15B C5B C10B C1B 107.7(6) . . . . ?
C15B C5B C10B C9B -75.8(6) . . . . ?
O1C C2C C3C C4C -76.4(6) . . . . ?
O2C C9C C10C C1C -108.5(6) . . . . ?
O2C C9C C10C C5C 72.3(7) . . . . ?
C1C C2C C3C C4C 43.5(7) . . . . ?
C2C C1C C10C C5C -0.6(10) . . . . ?
C2C C1C C10C C9C -179.7(5) . . . . ?
C2C C3C C4C C5C -63.5(7) . . . . ?
C2C C3C C4C C14C 169.4(5) . . . . ?
C3C C4C C5C C6C 165.0(5) . . . . ?
C3C C4C C5C C10C 48.0(7) . . . . ?
C3C C4C C5C C15C -73.9(6) . . . . ?
C4C C5C C6C C7C -167.1(5) . . . . ?
C4C C5C C10C C1C -17.8(8) . . . . ?
C4C C5C C10C C9C 161.3(5) . . . . ?
C5C C6C C7C C8C 57.5(6) . . . . ?
C5C C6C C7C C11C -179.0(5) . . . . ?
C6C C5C C10C C1C -133.7(6) . . . . ?
C6C C5C C10C C9C 45.4(7) . . . . ?
C6C C7C C8C C9C -57.8(6) . . . . ?
C6C C7C C11C C12C 132.7(6) . . . . ?
C6C C7C C11C C13C -49.4(8) . . . . ?
C7C C8C C9C O2C -70.3(5) . . . . ?
C7C C8C C9C C10C 52.7(6) . . . . ?
C8C C7C C11C C12C -105.4(7) . . . . ?
C8C C7C C11C C13C 72.5(7) . . . . ?
C8C C9C C10C C1C 131.1(6) . . . . ?
C8C C9C C10C C5C -48.0(7) . . . . ?
C10C C1C C2C O1C 111.3(6) . . . . ?
C10C C1C C2C C3C -11.9(9) . . . . ?
C10C C5C C6C C7C -50.2(6) . . . . ?
C11C C7C C8C C9C 178.5(4) . . . . ?
C14C C4C C5C C6C -69.9(7) . . . . ?
C14C C4C C5C C10C 173.1(6) . . . . ?
C14C C4C C5C C15C 51.3(8) . . . . ?
C15C C5C C6C C7C 71.1(6) . . . . ?
C15C C5C C10C C1C 104.8(6) . . . . ?
C15C C5C C10C C9C -76.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
