# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 
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data_DK103_020816_0m
_database_code_depnum_ccdc_archive 'CCDC 1510253'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 O5'
_chemical_formula_sum            'C12 H18 O5'
_chemical_formula_weight         242.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.2841(15)
_cell_length_b                   10.607(4)
_cell_length_c                   18.103(4)
_cell_angle_alpha                98.128(6)
_cell_angle_beta                 97.616(5)
_cell_angle_gamma                96.180(10)
_cell_volume                     1174.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1003
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      27.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16121
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.956
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4599
_reflns_number_gt                3524
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+1.6401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4599
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5895(4) 0.4417(2) 0.41746(11) 0.0195(5) Uani 1 1 d . . . . .
O2 O 0.8206(3) 0.4364(2) 0.32811(12) 0.0165(5) Uani 1 1 d . . . . .
O3 O 0.9281(4) 0.5791(2) 0.25633(12) 0.0213(5) Uani 1 1 d . . . . .
O4 O 0.4137(3) 0.2991(2) 0.22602(11) 0.0151(5) Uani 1 1 d . . . . .
H4C H 0.3118 0.3072 0.1927 0.023 Uiso 1 1 calc R U . . .
O5 O 0.4826(3) 0.5377(2) 0.18455(11) 0.0151(5) Uani 1 1 d . . . . .
H5C H 0.5744 0.5079 0.1595 0.023 Uiso 1 1 calc R U . . .
C1 C 0.6153(5) 0.3785(3) 0.34670(16) 0.0103(6) Uani 1 1 d . . . . .
C2 C 0.6345(5) 0.2403(3) 0.35510(17) 0.0152(7) Uani 1 1 d . . . . .
H2A H 0.7309 0.2034 0.3211 0.018 Uiso 1 1 calc R U . . .
H2B H 0.4908 0.1876 0.3434 0.018 Uiso 1 1 calc R U . . .
C3 C 0.7310(5) 0.2461(3) 0.43793(16) 0.0123(6) Uani 1 1 d . . . . .
C4 C 0.6355(6) 0.3626(3) 0.47457(18) 0.0226(8) Uani 1 1 d . . . . .
H4A H 0.5012 0.3341 0.4939 0.027 Uiso 1 1 calc R U . . .
H4B H 0.7404 0.4117 0.5173 0.027 Uiso 1 1 calc R U . . .
C5 C 0.9780(5) 0.2620(3) 0.45481(18) 0.0213(7) Uani 1 1 d . . . . .
H5A H 1.0399 0.3514 0.4536 0.026 Uiso 1 1 calc R U . . .
H5B H 1.0382 0.2033 0.4178 0.026 Uiso 1 1 calc R U . . .
C6 C 1.0268(6) 0.2275(3) 0.53485(19) 0.0263(8) Uani 1 1 d . . . . .
H6A H 1.1596 0.1850 0.5400 0.032 Uiso 1 1 calc R U . . .
H6B H 1.0474 0.3057 0.5734 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8287(5) 0.1357(3) 0.54435(18) 0.0222(8) Uani 1 1 d . . . . .
H7A H 0.8708 0.0506 0.5517 0.027 Uiso 1 1 calc R U . . .
H7B H 0.7631 0.1708 0.5884 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6696(5) 0.1249(3) 0.47124(18) 0.0177(7) Uani 1 1 d . . . . .
H8B H 0.6833 0.0470 0.4358 0.021 Uiso 1 1 calc R U . . .
H8A H 0.5187 0.1205 0.4819 0.021 Uiso 1 1 calc R U . . .
C9 C 0.4406(5) 0.4042(3) 0.28507(16) 0.0120(6) Uani 1 1 d . . . . .
H9 H 0.3016 0.4160 0.3049 0.014 Uiso 1 1 calc R U . . .
C10 C 0.5415(5) 0.5282(3) 0.26176(15) 0.0110(6) Uani 1 1 d . . . . .
C11 C 0.7843(5) 0.5212(3) 0.27976(16) 0.0135(7) Uani 1 1 d . . . . .
C12 C 0.4824(5) 0.6477(3) 0.30907(17) 0.0162(7) Uani 1 1 d . . . . .
H12B H 0.5645 0.7248 0.2978 0.024 Uiso 1 1 calc R U . . .
H12C H 0.5179 0.6424 0.3628 0.024 Uiso 1 1 calc R U . . .
H12A H 0.3271 0.6522 0.2968 0.024 Uiso 1 1 calc R U . . .
O1' O 0.3044(3) 0.89809(18) 0.07919(11) 0.0105(4) Uani 1 1 d . . . . .
O2' O 0.0009(3) 0.78133(19) 0.00089(11) 0.0119(5) Uani 1 1 d . . . . .
O3' O -0.0429(3) 0.6934(2) -0.12086(11) 0.0164(5) Uani 1 1 d . . . . .
O4' O 0.1617(3) 0.55842(19) 0.06979(11) 0.0116(5) Uani 1 1 d . . . . .
H4'C H 0.2257 0.5395 0.1097 0.017 Uiso 1 1 calc R U . . .
O5' O 0.2706(3) 0.5299(2) -0.07219(11) 0.0143(5) Uani 1 1 d . . . . .
H5'C H 0.1510 0.4863 -0.0720 0.021 Uiso 1 1 calc R U . . .
C1' C 0.1619(5) 0.7859(3) 0.06966(16) 0.0108(6) Uani 1 1 d . . . . .
C2' C 0.0430(5) 0.7952(3) 0.13753(17) 0.0172(7) Uani 1 1 d . . . . .
H2'B H 0.1182 0.7560 0.1784 0.021 Uiso 1 1 calc R U . . .
H2'A H -0.1073 0.7515 0.1236 0.021 Uiso 1 1 calc R U . . .
C3' C 0.0451(5) 0.9410(3) 0.16249(16) 0.0110(6) Uani 1 1 d . . . . .
C4' C 0.2017(5) 1.0016(3) 0.11508(17) 0.0145(7) Uani 1 1 d . . . . .
H4'B H 0.1218 1.0435 0.0765 0.017 Uiso 1 1 calc R U . . .
H4'A H 0.3118 1.0669 0.1477 0.017 Uiso 1 1 calc R U . . .
C5' C -0.1817(5) 0.9817(3) 0.15109(18) 0.0168(7) Uani 1 1 d . . . . .
H5'A H -0.2638 0.9393 0.1018 0.020 Uiso 1 1 calc R U . . .
H5'B H -0.1739 1.0759 0.1535 0.020 Uiso 1 1 calc R U . . .
C6' C -0.2877(5) 0.9378(3) 0.21627(17) 0.0166(7) Uani 1 1 d . . . . .
H6'A H -0.3737 0.8521 0.2001 0.020 Uiso 1 1 calc R U . . .
H6'B H -0.3841 0.9995 0.2343 0.020 Uiso 1 1 calc R U . . .
C7' C -0.0970(5) 0.9324(3) 0.27921(16) 0.0146(7) Uani 1 1 d . . . . .
H7'A H -0.1105 0.9892 0.3262 0.017 Uiso 1 1 calc R U . . .
H7'B H -0.0938 0.8436 0.2901 0.017 Uiso 1 1 calc R U . . .
C8' C 0.1078(5) 0.9783(3) 0.24817(16) 0.0159(7) Uani 1 1 d . . . . .
H8'A H 0.2311 0.9349 0.2670 0.019 Uiso 1 1 calc R U . . .
H8'B H 0.1471 1.0724 0.2625 0.019 Uiso 1 1 calc R U . . .
C9' C 0.2787(5) 0.6691(3) 0.05131(16) 0.0108(6) Uani 1 1 d . . . . .
H9' H 0.4314 0.6838 0.0778 0.013 Uiso 1 1 calc R U . . .
C10' C 0.2703(4) 0.6557(3) -0.03472(16) 0.0097(6) Uani 1 1 d . . . . .
C11' C 0.0601(5) 0.7091(3) -0.05885(16) 0.0109(6) Uani 1 1 d . . . . .
C12' C 0.4583(5) 0.7402(3) -0.05568(17) 0.0157(7) Uani 1 1 d . . . . .
H12D H 0.5937 0.7051 -0.0422 0.024 Uiso 1 1 calc R U . . .
H12F H 0.4675 0.8276 -0.0282 0.024 Uiso 1 1 calc R U . . .
H12E H 0.4343 0.7420 -0.1101 0.024 Uiso 1 1 calc R U . . .


_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
O1 C1 1.397(3) . ?
O1 C4 1.440(4) . ?
O2 C11 1.357(4) . ?
O2 C1 1.469(3) . ?
O3 C11 1.196(4) . ?
O4 C9 1.410(3) . ?
O4 H4C 0.8400 . ?
O5 C10 1.418(3) . ?
O5 H5C 0.8400 . ?
C1 C2 1.511(4) . ?
C1 C9 1.533(4) . ?
C2 C3 1.531(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C5 1.528(4) . ?
C3 C8 1.529(4) . ?
C3 C4 1.537(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.544(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.540(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.532(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8B 0.9900 . ?
C8 H8A 0.9900 . ?
C9 C10 1.536(4) . ?
C9 H9 1.0000 . ?
C10 C11 1.529(4) . ?
C10 C12 1.535(4) . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12A 0.9800 . ?
O1' C1' 1.385(3) . ?
O1' C4' 1.451(3) . ?
O2' C11' 1.352(3) . ?
O2' C1' 1.488(3) . ?
O3' C11' 1.199(3) . ?
O4' C9' 1.422(3) . ?
O4' H4'C 0.8400 . ?
O5' C10' 1.409(3) . ?
O5' H5'C 0.8400 . ?
C1' C2' 1.518(4) . ?
C1' C9' 1.526(4) . ?
C2' C3' 1.546(4) . ?
C2' H2'B 0.9900 . ?
C2' H2'A 0.9900 . ?
C3' C5' 1.530(4) . ?
C3' C8' 1.532(4) . ?
C3' C4' 1.537(4) . ?
C4' H4'B 0.9900 . ?
C4' H4'A 0.9900 . ?
C5' C6' 1.533(4) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C6' C7' 1.552(4) . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C7' C8' 1.531(4) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C9' C10' 1.537(4) . ?
C9' H9' 1.0000 . ?
C10' C12' 1.526(4) . ?
C10' C11' 1.528(4) . ?
C12' H12D 0.9800 . ?
C12' H12F 0.9800 . ?
C12' H12E 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
C1 O1 C4 110.6(2) . . ?
C11 O2 C1 110.6(2) . . ?
C9 O4 H4C 109.5 . . ?
C10 O5 H5C 109.5 . . ?
O1 C1 O2 107.5(2) . . ?
O1 C1 C2 106.7(2) . . ?
O2 C1 C2 108.5(2) . . ?
O1 C1 C9 111.0(2) . . ?
O2 C1 C9 105.1(2) . . ?
C2 C1 C9 117.7(2) . . ?
C1 C2 C3 104.5(2) . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C5 C3 C8 101.8(2) . . ?
C5 C3 C2 115.8(3) . . ?
C8 C3 C2 114.6(2) . . ?
C5 C3 C4 112.5(3) . . ?
C8 C3 C4 112.3(3) . . ?
C2 C3 C4 100.5(2) . . ?
O1 C4 C3 107.4(2) . . ?
O1 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
O1 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C3 C5 C6 104.3(3) . . ?
C3 C5 H5A 110.9 . . ?
C6 C5 H5A 110.9 . . ?
C3 C5 H5B 110.9 . . ?
C6 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C7 C6 C5 105.8(3) . . ?
C7 C6 H6A 110.6 . . ?
C5 C6 H6A 110.6 . . ?
C7 C6 H6B 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
C8 C7 C6 105.6(3) . . ?
C8 C7 H7A 110.6 . . ?
C6 C7 H7A 110.6 . . ?
C8 C7 H7B 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.8 . . ?
C3 C8 C7 105.5(3) . . ?
C3 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
C3 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
H8B C8 H8A 108.8 . . ?
O4 C9 C1 107.0(2) . . ?
O4 C9 C10 112.0(2) . . ?
C1 C9 C10 102.9(2) . . ?
O4 C9 H9 111.5 . . ?
C1 C9 H9 111.5 . . ?
C10 C9 H9 111.5 . . ?
O5 C10 C11 110.7(2) . . ?
O5 C10 C12 107.8(2) . . ?
C11 C10 C12 109.9(2) . . ?
O5 C10 C9 114.3(2) . . ?
C11 C10 C9 102.7(2) . . ?
C12 C10 C9 111.4(2) . . ?
O3 C11 O2 122.3(3) . . ?
O3 C11 C10 127.6(3) . . ?
O2 C11 C10 110.1(2) . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
C1' O1' C4' 107.9(2) . . ?
C11' O2' C1' 110.4(2) . . ?
C9' O4' H4'C 109.5 . . ?
C10' O5' H5'C 109.5 . . ?
O1' C1' O2' 108.8(2) . . ?
O1' C1' C2' 106.3(2) . . ?
O2' C1' C2' 108.2(2) . . ?
O1' C1' C9' 110.5(2) . . ?
O2' C1' C9' 103.9(2) . . ?
C2' C1' C9' 118.9(3) . . ?
C1' C2' C3' 104.5(2) . . ?
C1' C2' H2'B 110.8 . . ?
C3' C2' H2'B 110.8 . . ?
C1' C2' H2'A 110.8 . . ?
C3' C2' H2'A 110.8 . . ?
H2'B C2' H2'A 108.9 . . ?
C5' C3' C8' 101.0(2) . . ?
C5' C3' C4' 114.1(2) . . ?
C8' C3' C4' 115.4(2) . . ?
C5' C3' C2' 112.2(3) . . ?
C8' C3' C2' 111.3(2) . . ?
C4' C3' C2' 103.2(2) . . ?
O1' C4' C3' 106.7(2) . . ?
O1' C4' H4'B 110.4 . . ?
C3' C4' H4'B 110.4 . . ?
O1' C4' H4'A 110.4 . . ?
C3' C4' H4'A 110.4 . . ?
H4'B C4' H4'A 108.6 . . ?
C3' C5' C6' 104.4(2) . . ?
C3' C5' H5'A 110.9 . . ?
C6' C5' H5'A 110.9 . . ?
C3' C5' H5'B 110.9 . . ?
C6' C5' H5'B 110.9 . . ?
H5'A C5' H5'B 108.9 . . ?
C5' C6' C7' 105.3(2) . . ?
C5' C6' H6'A 110.7 . . ?
C7' C6' H6'A 110.7 . . ?
C5' C6' H6'B 110.7 . . ?
C7' C6' H6'B 110.7 . . ?
H6'A C6' H6'B 108.8 . . ?
C8' C7' C6' 105.4(2) . . ?
C8' C7' H7'A 110.7 . . ?
C6' C7' H7'A 110.7 . . ?
C8' C7' H7'B 110.7 . . ?
C6' C7' H7'B 110.7 . . ?
H7'A C7' H7'B 108.8 . . ?
C7' C8' C3' 103.8(2) . . ?
C7' C8' H8'A 111.0 . . ?
C3' C8' H8'A 111.0 . . ?
C7' C8' H8'B 111.0 . . ?
C3' C8' H8'B 111.0 . . ?
H8'A C8' H8'B 109.0 . . ?
O4' C9' C1' 109.9(2) . . ?
O4' C9' C10' 109.6(2) . . ?
C1' C9' C10' 103.0(2) . . ?
O4' C9' H9' 111.3 . . ?
C1' C9' H9' 111.3 . . ?
C10' C9' H9' 111.3 . . ?
O5' C10' C12' 107.5(2) . . ?
O5' C10' C11' 111.8(2) . . ?
C12' C10' C11' 108.6(2) . . ?
O5' C10' C9' 115.3(2) . . ?
C12' C10' C9' 111.4(2) . . ?
C11' C10' C9' 102.1(2) . . ?
O3' C11' O2' 122.4(3) . . ?
O3' C11' C10' 127.4(3) . . ?
O2' C11' C10' 110.2(2) . . ?
C10' C12' H12D 109.5 . . ?
C10' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
C10' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
H12F C12' H12E 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
C4 O1 C1 O2 -104.2(3) . . . . ?
C4 O1 C1 C2 12.0(3) . . . . ?
C4 O1 C1 C9 141.4(3) . . . . ?
C11 O2 C1 O1 -100.5(3) . . . . ?
C11 O2 C1 C2 144.4(2) . . . . ?
C11 O2 C1 C9 17.8(3) . . . . ?
O1 C1 C2 C3 -28.0(3) . . . . ?
O2 C1 C2 C3 87.5(3) . . . . ?
C9 C1 C2 C3 -153.4(3) . . . . ?
C1 C2 C3 C5 -90.0(3) . . . . ?
C1 C2 C3 C8 152.0(3) . . . . ?
C1 C2 C3 C4 31.3(3) . . . . ?
C1 O1 C4 C3 8.8(3) . . . . ?
C5 C3 C4 O1 98.7(3) . . . . ?
C8 C3 C4 O1 -147.2(3) . . . . ?
C2 C3 C4 O1 -25.0(3) . . . . ?
C8 C3 C5 C6 -40.0(3) . . . . ?
C2 C3 C5 C6 -164.9(3) . . . . ?
C4 C3 C5 C6 80.4(3) . . . . ?
C3 C5 C6 C7 26.4(3) . . . . ?
C5 C6 C7 C8 -2.3(4) . . . . ?
C5 C3 C8 C7 39.0(3) . . . . ?
C2 C3 C8 C7 164.6(3) . . . . ?
C4 C3 C8 C7 -81.5(3) . . . . ?
C6 C7 C8 C3 -22.8(3) . . . . ?
O1 C1 C9 O4 -154.0(2) . . . . ?
O2 C1 C9 O4 90.1(3) . . . . ?
C2 C1 C9 O4 -30.7(3) . . . . ?
O1 C1 C9 C10 87.9(3) . . . . ?
O2 C1 C9 C10 -28.0(3) . . . . ?
C2 C1 C9 C10 -148.8(3) . . . . ?
O4 C9 C10 O5 32.8(3) . . . . ?
C1 C9 C10 O5 147.4(2) . . . . ?
O4 C9 C10 C11 -87.1(3) . . . . ?
C1 C9 C10 C11 27.5(3) . . . . ?
O4 C9 C10 C12 155.3(2) . . . . ?
C1 C9 C10 C12 -90.1(3) . . . . ?
C1 O2 C11 O3 -179.3(3) . . . . ?
C1 O2 C11 C10 0.5(3) . . . . ?
O5 C10 C11 O3 39.0(4) . . . . ?
C12 C10 C11 O3 -79.9(4) . . . . ?
C9 C10 C11 O3 161.5(3) . . . . ?
O5 C10 C11 O2 -140.7(2) . . . . ?
C12 C10 C11 O2 100.3(3) . . . . ?
C9 C10 C11 O2 -18.3(3) . . . . ?
C4' O1' C1' O2' 81.2(3) . . . . ?
C4' O1' C1' C2' -35.1(3) . . . . ?
C4' O1' C1' C9' -165.5(2) . . . . ?
C11' O2' C1' O1' 97.2(3) . . . . ?
C11' O2' C1' C2' -147.7(2) . . . . ?
C11' O2' C1' C9' -20.5(3) . . . . ?
O1' C1' C2' C3' 27.6(3) . . . . ?
O2' C1' C2' C3' -89.0(3) . . . . ?
C9' C1' C2' C3' 153.0(3) . . . . ?
C1' C2' C3' C5' 113.3(3) . . . . ?
C1' C2' C3' C8' -134.3(3) . . . . ?
C1' C2' C3' C4' -10.0(3) . . . . ?
C1' O1' C4' C3' 28.4(3) . . . . ?
C5' C3' C4' O1' -131.8(3) . . . . ?
C8' C3' C4' O1' 111.9(3) . . . . ?
C2' C3' C4' O1' -9.8(3) . . . . ?
C8' C3' C5' C6' -42.2(3) . . . . ?
C4' C3' C5' C6' -166.6(2) . . . . ?
C2' C3' C5' C6' 76.4(3) . . . . ?
C3' C5' C6' C7' 25.0(3) . . . . ?
C5' C6' C7' C8' 2.1(3) . . . . ?
C6' C7' C8' C3' -28.3(3) . . . . ?
C5' C3' C8' C7' 43.4(3) . . . . ?
C4' C3' C8' C7' 166.9(2) . . . . ?
C2' C3' C8' C7' -75.9(3) . . . . ?
O1' C1' C9' O4' 157.8(2) . . . . ?
O2' C1' C9' O4' -85.7(3) . . . . ?
C2' C1' C9' O4' 34.5(3) . . . . ?
O1' C1' C9' C10' -85.4(3) . . . . ?
O2' C1' C9' C10' 31.1(3) . . . . ?
C2' C1' C9' C10' 151.3(3) . . . . ?
O4' C9' C10' O5' -34.5(3) . . . . ?
C1' C9' C10' O5' -151.4(2) . . . . ?
O4' C9' C10' C12' -157.3(2) . . . . ?
C1' C9' C10' C12' 85.7(3) . . . . ?
O4' C9' C10' C11' 86.9(3) . . . . ?
C1' C9' C10' C11' -30.0(3) . . . . ?
C1' O2' C11' O3' -178.6(3) . . . . ?
C1' O2' C11' C10' 0.8(3) . . . . ?
O5' C10' C11' O3' -37.9(4) . . . . ?
C12' C10' C11' O3' 80.5(4) . . . . ?
C9' C10' C11' O3' -161.8(3) . . . . ?
O5' C10' C11' O2' 142.8(2) . . . . ?
C12' C10' C11' O2' -98.8(3) . . . . ?
C9' C10' C11' O2' 19.0(3) . . . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.067



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-petroleum ether'
####################################################################### 
# 
# 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_DK101
_database_code_depnum_ccdc_archive 'CCDC 1510252'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 O3'
_chemical_formula_sum            'C25 H26 O3'
_chemical_formula_weight         374.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7173(8)
_cell_length_b                   22.6030(13)
_cell_length_c                   8.9795(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.612(2)
_cell_angle_gamma                90
_cell_volume                     1993.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2791
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      27.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24001
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.802
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3912
_reflns_number_gt                3378
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+2.8023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56789(17) 0.18311(7) 0.88448(19) 0.0227(4) Uani 1 1 d . . . . .
O2 O 0.65531(16) 0.26038(7) 1.06661(19) 0.0217(4) Uani 1 1 d . . . . .
O3 O 0.67146(17) 0.35899(8) 1.0835(2) 0.0250(4) Uani 1 1 d . . . . .
C1 C 0.5471(2) 0.21668(10) 1.0032(3) 0.0187(5) Uani 1 1 d . . . . .
C2 C 0.5559(3) 0.17414(11) 1.1377(3) 0.0234(5) Uani 1 1 d . . . . .
H2A H 0.4655 0.1568 1.1166 0.028 Uiso 1 1 calc R U . . .
H2B H 0.5899 0.1946 1.2441 0.028 Uiso 1 1 calc R U . . .
C3 C 0.6555(3) 0.12633(11) 1.1354(3) 0.0233(5) Uani 1 1 d . . . . .
C4 C 0.8009(3) 0.14097(13) 1.2564(3) 0.0317(6) Uani 1 1 d . . . . .
H4A H 0.8318 0.1775 1.2207 0.038 Uiso 1 1 calc R U . . .
H4B H 0.8002 0.1487 1.3645 0.038 Uiso 1 1 calc R U . . .
C5 C 0.9012(3) 0.09146(13) 1.2713(3) 0.0335(7) Uani 1 1 d . . . . .
H5A H 0.9918 0.1021 1.3547 0.040 Uiso 1 1 calc R U . . .
H5B H 0.9099 0.0865 1.1663 0.040 Uiso 1 1 calc R U . . .
C6 C 0.8539(3) 0.03358(14) 1.3181(3) 0.0389(7) Uani 1 1 d . . . . .
H6A H 0.9193 0.0018 1.3239 0.047 Uiso 1 1 calc R U . . .
H6B H 0.8520 0.0377 1.4269 0.047 Uiso 1 1 calc R U . . .
C7 C 0.7137(3) 0.01688(12) 1.1956(4) 0.0361(7) Uani 1 1 d . . . . .
H7A H 0.6838 -0.0200 1.2309 0.043 Uiso 1 1 calc R U . . .
H7B H 0.7175 0.0094 1.0889 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6117(3) 0.06571(12) 1.1783(3) 0.0306(6) Uani 1 1 d . . . . .
H8A H 0.5996 0.0694 1.2816 0.037 Uiso 1 1 calc R U . . .
H8B H 0.5226 0.0546 1.0924 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6431(3) 0.12987(12) 0.9590(3) 0.0329(7) Uani 1 1 d . . . . .
H9A H 0.7349 0.1311 0.9573 0.039 Uiso 1 1 calc R U . . .
H9B H 0.5949 0.0946 0.8976 0.039 Uiso 1 1 calc R U . . .
C10 C 0.4184(2) 0.25329(10) 0.9312(3) 0.0177(5) Uani 1 1 d . . . . .
C11 C 0.4505(2) 0.31088(10) 0.9519(3) 0.0183(5) Uani 1 1 d . . . . .
C12 C 0.6011(2) 0.31554(11) 1.0409(3) 0.0196(5) Uani 1 1 d . . . . .
C13 C 0.2828(2) 0.22494(10) 0.8637(3) 0.0182(5) Uani 1 1 d . . . . .
C14 C 0.1747(3) 0.24984(11) 0.8909(3) 0.0248(5) Uani 1 1 d . . . . .
H14 H 0.1883 0.2857 0.9507 0.030 Uiso 1 1 calc R U . . .
C15 C 0.0479(3) 0.22312(12) 0.8321(4) 0.0333(7) Uani 1 1 d . . . . .
H15 H -0.0245 0.2407 0.8517 0.040 Uiso 1 1 calc R U . . .
C16 C 0.0262(3) 0.17092(13) 0.7449(4) 0.0375(7) Uani 1 1 d . . . . .
H16 H -0.0610 0.1527 0.7039 0.045 Uiso 1 1 calc R U . . .
C17 C 0.1326(3) 0.14545(12) 0.7181(3) 0.0353(7) Uani 1 1 d . . . . .
H17 H 0.1181 0.1096 0.6584 0.042 Uiso 1 1 calc R U . . .
C18 C 0.2603(3) 0.17165(11) 0.7775(3) 0.0265(6) Uani 1 1 d . . . . .
H18 H 0.3328 0.1533 0.7595 0.032 Uiso 1 1 calc R U . . .
C19 C 0.3683(2) 0.36472(10) 0.8901(3) 0.0171(5) Uani 1 1 d . . . . .
C20 C 0.3968(2) 0.41699(10) 0.9806(3) 0.0197(5) Uani 1 1 d . . . . .
H20 H 0.4662 0.4174 1.0874 0.024 Uiso 1 1 calc R U . . .
C21 C 0.3246(2) 0.46834(11) 0.9158(3) 0.0203(5) Uani 1 1 d . . . . .
H21 H 0.3451 0.5034 0.9793 0.024 Uiso 1 1 calc R U . . .
C22 C 0.2228(2) 0.46934(10) 0.7598(3) 0.0179(5) Uani 1 1 d . . . . .
C23 C 0.1953(2) 0.41736(10) 0.6692(3) 0.0196(5) Uani 1 1 d . . . . .
H23 H 0.1269 0.4173 0.5617 0.024 Uiso 1 1 calc R U . . .
C24 C 0.2656(2) 0.36582(10) 0.7327(3) 0.0180(5) Uani 1 1 d . . . . .
H24 H 0.2442 0.3308 0.6691 0.022 Uiso 1 1 calc R U . . .
C25 C 0.1453(3) 0.52563(11) 0.6906(3) 0.0259(6) Uani 1 1 d . . . . .
H25A H 0.1309 0.5293 0.5761 0.039 Uiso 1 1 calc R U . . .
H25B H 0.1978 0.5596 0.7516 0.039 Uiso 1 1 calc R U . . .
H25C H 0.0571 0.5244 0.6992 0.039 Uiso 1 1 calc R U . . .


_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
O1 C1 1.397(3) . ?
O1 C9 1.454(3) . ?
O2 C12 1.356(3) . ?
O2 C1 1.454(3) . ?
O3 C12 1.203(3) . ?
C1 C10 1.514(3) . ?
C1 C2 1.517(3) . ?
C2 C3 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.537(4) . ?
C3 C9 1.538(3) . ?
C3 C8 1.546(4) . ?
C4 C5 1.520(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.521(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.512(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.517(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.340(3) . ?
C10 C13 1.478(3) . ?
C11 C19 1.475(3) . ?
C11 C12 1.491(3) . ?
C13 C14 1.395(3) . ?
C13 C18 1.399(3) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.396(3) . ?
C19 C24 1.401(3) . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(3) . ?
C22 C25 1.510(3) . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C1 O1 C9 109.08(17) . . ?
C12 O2 C1 109.76(18) . . ?
O1 C1 O2 108.77(18) . . ?
O1 C1 C10 111.57(18) . . ?
O2 C1 C10 104.07(18) . . ?
O1 C1 C2 106.57(19) . . ?
O2 C1 C2 109.49(18) . . ?
C10 C1 C2 116.2(2) . . ?
C1 C2 C3 105.02(19) . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C2 C3 C4 110.8(2) . . ?
C2 C3 C9 101.83(19) . . ?
C4 C3 C9 111.2(2) . . ?
C2 C3 C8 109.9(2) . . ?
C4 C3 C8 109.7(2) . . ?
C9 C3 C8 113.2(2) . . ?
C5 C4 C3 112.6(2) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 C6 110.9(2) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 110.9(2) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 111.0(2) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C3 113.1(2) . . ?
C7 C8 H8A 109.0 . . ?
C3 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C3 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O1 C9 C3 108.7(2) . . ?
O1 C9 H9A 110.0 . . ?
C3 C9 H9A 110.0 . . ?
O1 C9 H9B 110.0 . . ?
C3 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
C11 C10 C13 129.3(2) . . ?
C11 C10 C1 109.4(2) . . ?
C13 C10 C1 121.1(2) . . ?
C10 C11 C19 131.9(2) . . ?
C10 C11 C12 107.8(2) . . ?
C19 C11 C12 119.9(2) . . ?
O3 C12 O2 121.7(2) . . ?
O3 C12 C11 129.4(2) . . ?
O2 C12 C11 108.9(2) . . ?
C14 C13 C18 118.2(2) . . ?
C14 C13 C10 120.1(2) . . ?
C18 C13 C10 121.6(2) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C20 C19 C24 118.2(2) . . ?
C20 C19 C11 121.4(2) . . ?
C24 C19 C11 120.2(2) . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C23 118.2(2) . . ?
C21 C22 C25 120.6(2) . . ?
C23 C22 C25 121.2(2) . . ?
C24 C23 C22 121.2(2) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C19 120.7(2) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C9 O1 C1 O2 94.4(2) . . . . ?
C9 O1 C1 C10 -151.4(2) . . . . ?
C9 O1 C1 C2 -23.6(3) . . . . ?
C12 O2 C1 O1 120.25(19) . . . . ?
C12 O2 C1 C10 1.2(2) . . . . ?
C12 O2 C1 C2 -123.7(2) . . . . ?
O1 C1 C2 C3 30.8(2) . . . . ?
O2 C1 C2 C3 -86.7(2) . . . . ?
C10 C1 C2 C3 155.8(2) . . . . ?
C1 C2 C3 C4 93.5(2) . . . . ?
C1 C2 C3 C9 -24.8(3) . . . . ?
C1 C2 C3 C8 -145.0(2) . . . . ?
C2 C3 C4 C5 174.0(2) . . . . ?
C9 C3 C4 C5 -73.5(3) . . . . ?
C8 C3 C4 C5 52.4(3) . . . . ?
C3 C4 C5 C6 -56.0(3) . . . . ?
C4 C5 C6 C7 57.5(3) . . . . ?
C5 C6 C7 C8 -56.9(3) . . . . ?
C6 C7 C8 C3 55.0(3) . . . . ?
C2 C3 C8 C7 -174.1(2) . . . . ?
C4 C3 C8 C7 -52.0(3) . . . . ?
C9 C3 C8 C7 72.8(3) . . . . ?
C1 O1 C9 C3 7.3(3) . . . . ?
C2 C3 C9 O1 11.6(3) . . . . ?
C4 C3 C9 O1 -106.4(3) . . . . ?
C8 C3 C9 O1 129.5(2) . . . . ?
O1 C1 C10 C11 -117.2(2) . . . . ?
O2 C1 C10 C11 0.0(2) . . . . ?
C2 C1 C10 C11 120.4(2) . . . . ?
O1 C1 C10 C13 67.3(3) . . . . ?
O2 C1 C10 C13 -175.61(18) . . . . ?
C2 C1 C10 C13 -55.2(3) . . . . ?
C13 C10 C11 C19 -12.9(4) . . . . ?
C1 C10 C11 C19 172.0(2) . . . . ?
C13 C10 C11 C12 174.1(2) . . . . ?
C1 C10 C11 C12 -1.0(2) . . . . ?
C1 O2 C12 O3 179.9(2) . . . . ?
C1 O2 C12 C11 -1.9(2) . . . . ?
C10 C11 C12 O3 179.9(2) . . . . ?
C19 C11 C12 O3 5.9(4) . . . . ?
C10 C11 C12 O2 1.8(2) . . . . ?
C19 C11 C12 O2 -172.22(19) . . . . ?
C11 C10 C13 C14 -34.8(4) . . . . ?
C1 C10 C13 C14 139.8(2) . . . . ?
C11 C10 C13 C18 147.9(2) . . . . ?
C1 C10 C13 C18 -37.5(3) . . . . ?
C18 C13 C14 C15 -1.0(4) . . . . ?
C10 C13 C14 C15 -178.3(2) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C13 -0.9(4) . . . . ?
C14 C13 C18 C17 1.4(4) . . . . ?
C10 C13 C18 C17 178.7(2) . . . . ?
C10 C11 C19 C20 148.0(3) . . . . ?
C12 C11 C19 C20 -39.7(3) . . . . ?
C10 C11 C19 C24 -37.1(4) . . . . ?
C12 C11 C19 C24 135.3(2) . . . . ?
C24 C19 C20 C21 0.3(3) . . . . ?
C11 C19 C20 C21 175.4(2) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C20 C21 C22 C25 -179.8(2) . . . . ?
C21 C22 C23 C24 0.8(3) . . . . ?
C25 C22 C23 C24 -179.6(2) . . . . ?
C22 C23 C24 C19 -0.8(4) . . . . ?
C20 C19 C24 C23 0.2(3) . . . . ?
C11 C19 C24 C23 -174.9(2) . . . . ?

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.053



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-petroleum ether'
####################################################################### 
# 
# 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_DAC092_130616_0m
_database_code_depnum_ccdc_archive 'CCDC 1510251'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 O4'
_chemical_formula_sum            'C20 H24 O4'
_chemical_formula_weight         328.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.3783(11)
_cell_length_b                   8.2958(12)
_cell_length_c                   14.771(2)
_cell_angle_alpha                80.166(7)
_cell_angle_beta                 82.665(8)
_cell_angle_gamma                70.592(7)
_cell_volume                     837.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7098
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      34.19

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'SADABS (BRUKER, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18583
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.403
_diffrn_reflns_theta_max         34.322
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5914
_reflns_number_gt                4574
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.2559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5914
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61835(11) 0.91695(9) 0.31235(5) 0.01478(16) Uani 1 1 d . . . . .
O2 O 0.92408(11) 0.72759(10) 0.33770(5) 0.01364(15) Uani 1 1 d . . . . .
O3 O 1.17968(11) 0.68916(11) 0.41569(6) 0.01841(17) Uani 1 1 d . . . . .
O4 O 0.98982(13) 0.79034(11) 0.85567(5) 0.02014(18) Uani 1 1 d . . . . .
C1 C 0.71952(15) 0.75451(13) 0.35931(7) 0.01226(19) Uani 1 1 d . . . . .
C2 C 0.65838(15) 0.62083(13) 0.32276(7) 0.01263(19) Uani 1 1 d . . . . .
H2A H 0.5515 0.5935 0.3630 0.015 Uiso 1 1 calc R U . . .
H2B H 0.7677 0.5131 0.3186 0.015 Uiso 1 1 calc R U . . .
C3 C 0.59249(15) 0.70799(13) 0.22634(7) 0.01274(19) Uani 1 1 d . . . . .
C4 C 0.50239(16) 0.89482(13) 0.24645(7) 0.0152(2) Uani 1 1 d . . . . .
H4A H 0.5037 0.9765 0.1893 0.018 Uiso 1 1 calc R U . . .
H4B H 0.3674 0.9155 0.2724 0.018 Uiso 1 1 calc R U . . .
C5 C 0.76417(16) 0.68787(14) 0.15324(7) 0.0158(2) Uani 1 1 d . . . . .
H5A H 0.8534 0.7421 0.1706 0.019 Uiso 1 1 calc R U . . .
H5B H 0.8349 0.5636 0.1527 0.019 Uiso 1 1 calc R U . . .
C6 C 0.70320(19) 0.76944(16) 0.05627(8) 0.0220(2) Uani 1 1 d . . . . .
H6A H 0.6469 0.8961 0.0544 0.026 Uiso 1 1 calc R U . . .
H6B H 0.8178 0.7455 0.0116 0.026 Uiso 1 1 calc R U . . .
C7 C 0.55555(19) 0.69776(17) 0.02893(8) 0.0238(3) Uani 1 1 d . . . . .
H7A H 0.5121 0.7575 -0.0322 0.029 Uiso 1 1 calc R U . . .
H7B H 0.6164 0.5734 0.0241 0.029 Uiso 1 1 calc R U . . .
C8 C 0.38218(18) 0.72209(16) 0.09957(8) 0.0213(2) Uani 1 1 d . . . . .
H8A H 0.2916 0.6698 0.0819 0.026 Uiso 1 1 calc R U . . .
H8B H 0.3141 0.8469 0.1000 0.026 Uiso 1 1 calc R U . . .
C9 C 0.44434(17) 0.63855(14) 0.19640(8) 0.0166(2) Uani 1 1 d . . . . .
H9A H 0.3296 0.6610 0.2410 0.020 Uiso 1 1 calc R U . . .
H9B H 0.5006 0.5121 0.1973 0.020 Uiso 1 1 calc R U . . .
C10 C 0.69118(15) 0.75993(12) 0.46206(7) 0.01235(19) Uani 1 1 d . . . . .
C11 C 0.85911(15) 0.74138(12) 0.49485(7) 0.01217(19) Uani 1 1 d . . . . .
C12 C 1.00845(15) 0.71691(13) 0.41627(7) 0.01293(19) Uani 1 1 d . . . . .
C13 C 0.49518(16) 0.79184(14) 0.50969(8) 0.0159(2) Uani 1 1 d . . . . .
H13A H 0.4667 0.6827 0.5255 0.024 Uiso 1 1 calc R U . . .
H13B H 0.4002 0.8725 0.4689 0.024 Uiso 1 1 calc R U . . .
H13C H 0.4893 0.8414 0.5661 0.024 Uiso 1 1 calc R U . . .
C14 C 0.90027(15) 0.74918(12) 0.58867(7) 0.01201(19) Uani 1 1 d . . . . .
C15 C 0.80779(15) 0.67873(13) 0.66692(7) 0.0136(2) Uani 1 1 d . . . . .
H15 H 0.7209 0.6201 0.6595 0.016 Uiso 1 1 calc R U . . .
C16 C 0.84174(16) 0.69366(13) 0.75453(7) 0.0149(2) Uani 1 1 d . . . . .
H16 H 0.7790 0.6447 0.8068 0.018 Uiso 1 1 calc R U . . .
C17 C 0.96783(16) 0.78043(13) 0.76627(7) 0.0142(2) Uani 1 1 d . . . . .
C18 C 1.06389(16) 0.84898(13) 0.68989(7) 0.0138(2) Uani 1 1 d . . . . .
H18 H 1.1518 0.9064 0.6976 0.017 Uiso 1 1 calc R U . . .
C19 C 1.02888(15) 0.83196(13) 0.60219(7) 0.01323(19) Uani 1 1 d . . . . .
H19 H 1.0946 0.8781 0.5500 0.016 Uiso 1 1 calc R U . . .
C20 C 1.1161(2) 0.87963(18) 0.86975(9) 0.0263(3) Uani 1 1 d . . . . .
H20A H 1.2471 0.8199 0.8457 0.039 Uiso 1 1 calc R U . . .
H20B H 1.1153 0.8828 0.9358 0.039 Uiso 1 1 calc R U . . .
H20C H 1.0730 0.9977 0.8375 0.039 Uiso 1 1 calc R U . . .


_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
O1 C1 1.4138(12) . ?
O1 C4 1.4463(13) . ?
O2 C12 1.3620(13) . ?
O2 C1 1.4516(13) . ?
O3 C12 1.2058(13) . ?
O4 C17 1.3703(13) . ?
O4 C20 1.4216(15) . ?
C1 C10 1.5118(15) . ?
C1 C2 1.5244(15) . ?
C2 C3 1.5426(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C9 1.5334(15) . ?
C3 C4 1.5344(15) . ?
C3 C5 1.5394(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5307(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5259(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5249(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5343(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3396(15) . ?
C10 C13 1.4852(15) . ?
C11 C14 1.4725(14) . ?
C11 C12 1.4859(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.3929(15) . ?
C14 C15 1.4057(14) . ?
C15 C16 1.3825(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.3938(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3939(15) . ?
C18 C19 1.3917(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C1 O1 C4 109.87(8) . . ?
C12 O2 C1 109.41(8) . . ?
C17 O4 C20 116.97(9) . . ?
O1 C1 O2 107.74(8) . . ?
O1 C1 C10 109.77(8) . . ?
O2 C1 C10 104.01(8) . . ?
O1 C1 C2 106.49(8) . . ?
O2 C1 C2 110.87(8) . . ?
C10 C1 C2 117.64(8) . . ?
C1 C2 C3 104.17(8) . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C9 C3 C4 112.05(9) . . ?
C9 C3 C5 109.68(9) . . ?
C4 C3 C5 112.06(9) . . ?
C9 C3 C2 112.02(8) . . ?
C4 C3 C2 99.06(8) . . ?
C5 C3 C2 111.66(9) . . ?
O1 C4 C3 106.27(8) . . ?
O1 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
O1 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C6 C5 C3 112.97(9) . . ?
C6 C5 H5A 109.0 . . ?
C3 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C3 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 110.85(10) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 110.97(10) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 111.16(10) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C3 C9 C8 112.09(9) . . ?
C3 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C3 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C13 130.17(10) . . ?
C11 C10 C1 109.90(9) . . ?
C13 C10 C1 119.84(9) . . ?
C10 C11 C14 129.53(10) . . ?
C10 C11 C12 107.32(9) . . ?
C14 C11 C12 123.10(9) . . ?
O3 C12 O2 121.29(10) . . ?
O3 C12 C11 129.39(10) . . ?
O2 C12 C11 109.31(9) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.02(10) . . ?
C19 C14 C11 120.45(9) . . ?
C15 C14 C11 121.50(9) . . ?
C16 C15 C14 120.81(10) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.12(10) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
O4 C17 C16 115.71(9) . . ?
O4 C17 C18 124.05(10) . . ?
C16 C17 C18 120.23(10) . . ?
C19 C18 C17 118.90(10) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C14 121.90(10) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 O1 C1 O2 117.09(9) . . . . ?
C4 O1 C1 C10 -130.26(9) . . . . ?
C4 O1 C1 C2 -1.90(11) . . . . ?
C12 O2 C1 O1 116.86(9) . . . . ?
C12 O2 C1 C10 0.38(10) . . . . ?
C12 O2 C1 C2 -126.98(9) . . . . ?
O1 C1 C2 C3 24.49(10) . . . . ?
O2 C1 C2 C3 -92.44(9) . . . . ?
C10 C1 C2 C3 148.08(9) . . . . ?
C1 C2 C3 C9 -153.66(9) . . . . ?
C1 C2 C3 C4 -35.33(10) . . . . ?
C1 C2 C3 C5 82.87(10) . . . . ?
C1 O1 C4 C3 -21.77(11) . . . . ?
C9 C3 C4 O1 153.29(9) . . . . ?
C5 C3 C4 O1 -82.92(10) . . . . ?
C2 C3 C4 O1 34.98(10) . . . . ?
C9 C3 C5 C6 53.88(12) . . . . ?
C4 C3 C5 C6 -71.23(12) . . . . ?
C2 C3 C5 C6 178.67(9) . . . . ?
C3 C5 C6 C7 -55.15(13) . . . . ?
C5 C6 C7 C8 55.55(13) . . . . ?
C6 C7 C8 C9 -56.43(13) . . . . ?
C4 C3 C9 C8 71.02(12) . . . . ?
C5 C3 C9 C8 -54.09(12) . . . . ?
C2 C3 C9 C8 -178.67(9) . . . . ?
C7 C8 C9 C3 56.40(13) . . . . ?
O1 C1 C10 C11 -114.06(10) . . . . ?
O2 C1 C10 C11 0.98(11) . . . . ?
C2 C1 C10 C11 124.02(10) . . . . ?
O1 C1 C10 C13 62.93(12) . . . . ?
O2 C1 C10 C13 177.98(8) . . . . ?
C2 C1 C10 C13 -58.99(13) . . . . ?
C13 C10 C11 C14 -0.84(18) . . . . ?
C1 C10 C11 C14 175.75(9) . . . . ?
C13 C10 C11 C12 -178.43(10) . . . . ?
C1 C10 C11 C12 -1.84(11) . . . . ?
C1 O2 C12 O3 177.63(9) . . . . ?
C1 O2 C12 C11 -1.49(11) . . . . ?
C10 C11 C12 O3 -176.90(11) . . . . ?
C14 C11 C12 O3 5.32(17) . . . . ?
C10 C11 C12 O2 2.12(11) . . . . ?
C14 C11 C12 O2 -175.66(8) . . . . ?
C10 C11 C14 C19 -139.33(11) . . . . ?
C12 C11 C14 C19 37.93(14) . . . . ?
C10 C11 C14 C15 38.73(16) . . . . ?
C12 C11 C14 C15 -144.01(10) . . . . ?
C19 C14 C15 C16 0.93(15) . . . . ?
C11 C14 C15 C16 -177.17(9) . . . . ?
C14 C15 C16 C17 0.47(16) . . . . ?
C20 O4 C17 C16 -179.39(10) . . . . ?
C20 O4 C17 C18 1.32(16) . . . . ?
C15 C16 C17 O4 179.13(9) . . . . ?
C15 C16 C17 C18 -1.55(16) . . . . ?
O4 C17 C18 C19 -179.56(9) . . . . ?
C16 C17 C18 C19 1.18(15) . . . . ?
C17 C18 C19 C14 0.27(15) . . . . ?
C15 C14 C19 C18 -1.31(15) . . . . ?
C11 C14 C19 C18 176.82(9) . . . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.056



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-petroleum ether'
####################################################################### 
# 
# 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_msb_164_160616_0m
_database_code_depnum_ccdc_archive 'CCDC 1510255'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 O3'
_chemical_formula_sum            'C19 H22 O3'
_chemical_formula_weight         298.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.4777(2)
_cell_length_b                   8.9647(2)
_cell_length_c                   13.3928(3)
_cell_angle_alpha                93.6160(10)
_cell_angle_beta                 92.6120(10)
_cell_angle_gamma                93.620(2)
_cell_volume                     773.67(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3958
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      31.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10344
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.525
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3006
_reflns_number_gt                2502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.4332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3006
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39126(18) 0.32530(12) 0.24699(8) 0.0180(3) Uani 1 1 d . . . . .
O2 O 0.12618(17) 0.41337(13) 0.14733(8) 0.0177(3) Uani 1 1 d . . . . .
O3 O -0.13935(17) 0.33879(13) 0.03984(9) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.3477(2) 0.39104(18) 0.15670(12) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.4709(3) 0.54146(18) 0.16454(12) 0.0181(4) Uani 1 1 d . . . . .
H2A H 0.3964 0.6162 0.1282 0.022 Uiso 1 1 calc R U . . .
H2B H 0.6085 0.5323 0.1363 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4936(3) 0.58775(18) 0.27812(12) 0.0164(4) Uani 1 1 d . . . . .
C4 C 0.4144(3) 0.44307(18) 0.32537(12) 0.0199(4) Uani 1 1 d . . . . .
H4A H 0.5147 0.4172 0.3785 0.024 Uiso 1 1 calc R U . . .
H4B H 0.2798 0.4576 0.3555 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3593(3) 0.71740(19) 0.30657(12) 0.0207(4) Uani 1 1 d . . . . .
H5A H 0.3966 0.8032 0.2664 0.025 Uiso 1 1 calc R U . . .
H5B H 0.2119 0.6855 0.2899 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3859(3) 0.7679(2) 0.41781(13) 0.0252(4) Uani 1 1 d . . . . .
H6A H 0.3018 0.8545 0.4319 0.030 Uiso 1 1 calc R U . . .
H6B H 0.3353 0.6856 0.4581 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6122(3) 0.8119(2) 0.44814(14) 0.0287(4) Uani 1 1 d . . . . .
H7A H 0.6262 0.8369 0.5213 0.034 Uiso 1 1 calc R U . . .
H7B H 0.6576 0.9024 0.4141 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7511(3) 0.6858(2) 0.42075(13) 0.0260(4) Uani 1 1 d . . . . .
H8A H 0.7193 0.6005 0.4623 0.031 Uiso 1 1 calc R U . . .
H8B H 0.8977 0.7213 0.4357 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7208(3) 0.6328(2) 0.30989(12) 0.0206(4) Uani 1 1 d . . . . .
H9A H 0.8048 0.5459 0.2964 0.025 Uiso 1 1 calc R U . . .
H9B H 0.7718 0.7140 0.2688 0.025 Uiso 1 1 calc R U . . .
C10 C 0.3810(2) 0.28441(18) 0.07030(12) 0.0156(3) Uani 1 1 d . . . . .
H10 H 0.5111 0.2476 0.0552 0.019 Uiso 1 1 calc R U . . .
C11 C 0.2047(2) 0.24697(17) 0.01657(12) 0.0153(3) Uani 1 1 d . . . . .
C12 C 0.0408(3) 0.33274(18) 0.06492(12) 0.0168(4) Uani 1 1 d . . . . .
C13 C 0.1712(2) 0.14152(17) -0.07234(12) 0.0149(3) Uani 1 1 d . . . . .
C14 C 0.3385(3) 0.06692(18) -0.10993(12) 0.0176(4) Uani 1 1 d . . . . .
H14 H 0.4724 0.0864 -0.0781 0.021 Uiso 1 1 calc R U . . .
C15 C 0.3119(3) -0.03420(18) -0.19231(12) 0.0181(4) Uani 1 1 d . . . . .
H15 H 0.4278 -0.0827 -0.2164 0.022 Uiso 1 1 calc R U . . .
C16 C 0.1177(3) -0.06626(18) -0.24077(12) 0.0181(4) Uani 1 1 d . . . . .
C17 C -0.0480(3) 0.00705(19) -0.20348(13) 0.0207(4) Uani 1 1 d . . . . .
H17 H -0.1818 -0.0135 -0.2352 0.025 Uiso 1 1 calc R U . . .
C18 C -0.0230(3) 0.10945(19) -0.12108(12) 0.0196(4) Uani 1 1 d . . . . .
H18 H -0.1393 0.1582 -0.0976 0.023 Uiso 1 1 calc R U . . .
C19 C 0.0894(3) -0.1782(2) -0.33000(13) 0.0260(4) Uani 1 1 d . . . . .
H19A H 0.2213 -0.1855 -0.3625 0.039 Uiso 1 1 calc R U . . .
H19B H -0.0148 -0.1455 -0.3777 0.039 Uiso 1 1 calc R U . . .
H19C H 0.0435 -0.2765 -0.3078 0.039 Uiso 1 1 calc R U . . .


_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
O1 C1 1.4032(19) . ?
O1 C4 1.4370(19) . ?
O2 C12 1.357(2) . ?
O2 C1 1.4622(19) . ?
O3 C12 1.205(2) . ?
C1 C10 1.486(2) . ?
C1 C2 1.518(2) . ?
C2 C3 1.549(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C5 1.535(2) . ?
C3 C9 1.535(2) . ?
C3 C4 1.548(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.528(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.523(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.527(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.530(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.334(2) . ?
C10 H10 0.9500 . ?
C11 C13 1.472(2) . ?
C11 C12 1.497(2) . ?
C13 C18 1.396(2) . ?
C13 C14 1.405(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(2) . ?
C16 C19 1.508(2) . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 O1 C4 107.70(12) . . ?
C12 O2 C1 109.50(12) . . ?
O1 C1 O2 109.08(12) . . ?
O1 C1 C10 110.12(13) . . ?
O2 C1 C10 103.63(12) . . ?
O1 C1 C2 105.83(13) . . ?
O2 C1 C2 109.90(13) . . ?
C10 C1 C2 118.11(13) . . ?
C1 C2 C3 105.16(13) . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C5 C3 C9 109.46(14) . . ?
C5 C3 C4 110.59(13) . . ?
C9 C3 C4 111.97(13) . . ?
C5 C3 C2 111.79(13) . . ?
C9 C3 C2 110.53(13) . . ?
C4 C3 C2 102.37(13) . . ?
O1 C4 C3 107.58(12) . . ?
O1 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
O1 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C6 C5 C3 112.34(14) . . ?
C6 C5 H5A 109.1 . . ?
C3 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C3 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 111.14(15) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 111.48(15) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 111.57(15) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C3 112.80(14) . . ?
C8 C9 H9A 109.0 . . ?
C3 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C3 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C1 111.36(14) . . ?
C11 C10 H10 124.3 . . ?
C1 C10 H10 124.3 . . ?
C10 C11 C13 128.10(15) . . ?
C10 C11 C12 106.55(14) . . ?
C13 C11 C12 125.35(14) . . ?
O3 C12 O2 121.21(15) . . ?
O3 C12 C11 129.85(15) . . ?
O2 C12 C11 108.92(13) . . ?
C18 C13 C14 117.64(15) . . ?
C18 C13 C11 122.62(15) . . ?
C14 C13 C11 119.73(14) . . ?
C15 C14 C13 121.19(15) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 121.08(15) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 117.78(15) . . ?
C17 C16 C19 121.48(15) . . ?
C15 C16 C19 120.74(15) . . ?
C18 C17 C16 121.71(15) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C13 120.60(15) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C4 O1 C1 O2 -82.97(14) . . . . ?
C4 O1 C1 C10 163.94(13) . . . . ?
C4 O1 C1 C2 35.22(16) . . . . ?
C12 O2 C1 O1 -118.38(14) . . . . ?
C12 O2 C1 C10 -1.10(15) . . . . ?
C12 O2 C1 C2 126.01(14) . . . . ?
O1 C1 C2 C3 -27.74(16) . . . . ?
O2 C1 C2 C3 89.91(14) . . . . ?
C10 C1 C2 C3 -151.57(14) . . . . ?
C1 C2 C3 C5 -108.21(15) . . . . ?
C1 C2 C3 C9 129.60(14) . . . . ?
C1 C2 C3 C4 10.18(16) . . . . ?
C1 O1 C4 C3 -28.63(16) . . . . ?
C5 C3 C4 O1 129.28(14) . . . . ?
C9 C3 C4 O1 -108.35(15) . . . . ?
C2 C3 C4 O1 10.05(16) . . . . ?
C9 C3 C5 C6 -55.17(18) . . . . ?
C4 C3 C5 C6 68.65(18) . . . . ?
C2 C3 C5 C6 -177.98(14) . . . . ?
C3 C5 C6 C7 56.39(19) . . . . ?
C5 C6 C7 C8 -54.8(2) . . . . ?
C6 C7 C8 C9 53.8(2) . . . . ?
C7 C8 C9 C3 -54.2(2) . . . . ?
C5 C3 C9 C8 54.10(18) . . . . ?
C4 C3 C9 C8 -68.90(18) . . . . ?
C2 C3 C9 C8 177.66(14) . . . . ?
O1 C1 C10 C11 116.30(15) . . . . ?
O2 C1 C10 C11 -0.25(17) . . . . ?
C2 C1 C10 C11 -122.03(16) . . . . ?
C1 C10 C11 C13 -178.00(14) . . . . ?
C1 C10 C11 C12 1.36(17) . . . . ?
C1 O2 C12 O3 -176.92(14) . . . . ?
C1 O2 C12 C11 1.94(16) . . . . ?
C10 C11 C12 O3 176.65(17) . . . . ?
C13 C11 C12 O3 -4.0(3) . . . . ?
C10 C11 C12 O2 -2.08(17) . . . . ?
C13 C11 C12 O2 177.31(14) . . . . ?
C10 C11 C13 C18 178.67(16) . . . . ?
C12 C11 C13 C18 -0.6(2) . . . . ?
C10 C11 C13 C14 -0.2(2) . . . . ?
C12 C11 C13 C14 -179.44(14) . . . . ?
C18 C13 C14 C15 0.2(2) . . . . ?
C11 C13 C14 C15 179.09(14) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C14 C15 C16 C19 -179.29(15) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C19 C16 C17 C18 179.61(16) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 0.1(2) . . . . ?
C11 C13 C18 C17 -178.74(15) . . . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.046



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-petroleum ether'
####################################################################### 
# 
# 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_SAGAR_MSB129_090616
_database_code_depnum_ccdc_archive 'CCDC 1510254'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 O4'
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.5888(15)
_cell_length_b                   19.163(3)
_cell_length_c                   6.1053(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1472.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1027
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      21.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18930
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.936
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2872
_reflns_number_gt                2445
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.984

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+3.4405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2872
_refine_ls_number_parameters     201
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1674
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3256(4) 0.6895(2) 0.5781(7) 0.0143(11) Uani 1 1 d . U . . .
O2 O 0.4774(3) 0.7104(2) 0.3692(7) 0.0113(10) Uani 1 1 d . U . . .
O3 O 0.5818(4) 0.6572(2) 0.1292(8) 0.0158(11) Uani 1 1 d . U . . .
O4 O 0.8214(4) 0.3716(2) 0.4663(7) 0.0171(11) Uani 1 1 d . . . . .
C1 C 0.4361(5) 0.6961(3) 0.5899(10) 0.0100(14) Uani 1 1 d . U . . .
C2 C 0.2756(5) 0.7562(3) 0.6240(12) 0.0149(14) Uani 1 1 d . U . . .
H2A H 0.2247 0.7513 0.7467 0.018 Uiso 1 1 calc R U . . .
H2B H 0.2365 0.7728 0.4935 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3626(5) 0.8074(3) 0.6840(10) 0.0095(14) Uani 1 1 d . U . . .
C4 C 0.4558(5) 0.7587(3) 0.7361(11) 0.0120(14) Uani 1 1 d . U . . .
H4A H 0.5245 0.7812 0.7009 0.014 Uiso 1 1 calc R U . . .
H4B H 0.4557 0.7451 0.8926 0.014 Uiso 1 1 calc R U . . .
C5 C 0.3907(6) 0.8602(4) 0.5023(11) 0.0185(16) Uani 1 1 d . . . . .
H5A H 0.4356 0.8381 0.3887 0.022 Uiso 1 1 calc R U . . .
H5B H 0.3255 0.8786 0.4322 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4508(6) 0.9180(4) 0.6182(15) 0.032(2) Uani 1 1 d . . . . .
H6A H 0.4374 0.9635 0.5466 0.038 Uiso 1 1 calc R U . . .
H6B H 0.5281 0.9086 0.6165 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4080(6) 0.9182(4) 0.8562(15) 0.033(2) Uani 1 1 d . . . . .
H7A H 0.4669 0.9124 0.9620 0.039 Uiso 1 1 calc R U . . .
H7B H 0.3709 0.9626 0.8882 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3313(6) 0.8571(4) 0.8707(12) 0.0216(17) Uani 1 1 d . . . . .
H8A H 0.2572 0.8732 0.8525 0.026 Uiso 1 1 calc R U . . .
H8B H 0.3379 0.8334 1.0142 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4879(5) 0.6289(3) 0.6511(10) 0.0082(13) Uani 1 1 d . U . . .
H9 H 0.4780 0.6057 0.7870 0.010 Uiso 1 1 calc R U . . .
C10 C 0.5502(5) 0.6055(3) 0.4882(11) 0.0096(13) Uani 1 1 d . U . . .
C11 C 0.5406(5) 0.6569(3) 0.3065(11) 0.0119(14) Uani 1 1 d . U . . .
C12 C 0.6168(5) 0.5423(3) 0.4814(11) 0.0096(13) Uani 1 1 d . U . . .
C13 C 0.6247(5) 0.4989(3) 0.6636(12) 0.0130(14) Uani 1 1 d . U . . .
H13 H 0.5839 0.5092 0.7904 0.016 Uiso 1 1 calc R U . . .
C14 C 0.6907(5) 0.4411(3) 0.6644(11) 0.0127(15) Uani 1 1 d . U . . .
H14 H 0.6945 0.4122 0.7906 0.015 Uiso 1 1 calc R U . . .
C15 C 0.7508(5) 0.4254(3) 0.4822(11) 0.0101(13) Uani 1 1 d . U . . .
C16 C 0.7433(5) 0.4673(3) 0.2937(11) 0.0119(14) Uani 1 1 d . U . . .
H16 H 0.7829 0.4560 0.1661 0.014 Uiso 1 1 calc R U . . .
C17 C 0.6774(5) 0.5253(3) 0.2963(11) 0.0124(14) Uani 1 1 d . U . . .
H17 H 0.6732 0.5540 0.1700 0.015 Uiso 1 1 calc R U . . .
C18 C 0.8279(6) 0.3260(4) 0.6532(11) 0.0214(17) Uani 1 1 d . . . . .
H18A H 0.8484 0.3530 0.7827 0.032 Uiso 1 1 calc R U . . .
H18B H 0.8811 0.2897 0.6255 0.032 Uiso 1 1 calc R U . . .
H18C H 0.7585 0.3041 0.6784 0.032 Uiso 1 1 calc R U . . .


_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
O1 C1 1.399(8) . ?
O1 C2 1.451(7) . ?
O2 C11 1.353(8) . ?
O2 C1 1.470(8) . ?
O3 C11 1.201(8) . ?
O4 C15 1.365(8) . ?
O4 C18 1.440(8) . ?
C1 C9 1.491(8) . ?
C1 C4 1.516(9) . ?
C2 C3 1.515(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.532(9) . ?
C3 C8 1.537(9) . ?
C3 C5 1.543(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.517(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.549(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.344(9) . ?
C9 H9 0.9500 . ?
C10 C12 1.473(9) . ?
C10 C11 1.487(9) . ?
C12 C13 1.393(9) . ?
C12 C17 1.402(9) . ?
C13 C14 1.386(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.406(9) . ?
C16 C17 1.387(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C1 O1 C2 110.0(5) . . ?
C11 O2 C1 109.0(5) . . ?
C15 O4 C18 116.0(5) . . ?
O1 C1 O2 108.8(5) . . ?
O1 C1 C9 111.6(5) . . ?
O2 C1 C9 103.6(5) . . ?
O1 C1 C4 105.4(5) . . ?
O2 C1 C4 109.6(5) . . ?
C9 C1 C4 117.7(5) . . ?
O1 C2 C3 107.7(5) . . ?
O1 C2 H2A 110.2 . . ?
C3 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C3 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
C2 C3 C4 102.1(5) . . ?
C2 C3 C8 113.3(6) . . ?
C4 C3 C8 114.8(5) . . ?
C2 C3 C5 114.6(6) . . ?
C4 C3 C5 111.9(5) . . ?
C8 C3 C5 100.7(5) . . ?
C1 C4 C3 103.5(5) . . ?
C1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
C6 C5 C3 104.9(6) . . ?
C6 C5 H5A 110.8 . . ?
C3 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
C3 C5 H5B 110.8 . . ?
H5A C5 H5B 108.8 . . ?
C5 C6 C7 105.5(6) . . ?
C5 C6 H6A 110.7 . . ?
C7 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
C7 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C8 C7 C6 105.8(6) . . ?
C8 C7 H7A 110.6 . . ?
C6 C7 H7A 110.6 . . ?
C8 C7 H7B 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
C7 C8 C3 105.8(6) . . ?
C7 C8 H8A 110.6 . . ?
C3 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
C3 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C10 C9 C1 111.0(5) . . ?
C10 C9 H9 124.5 . . ?
C1 C9 H9 124.5 . . ?
C9 C10 C12 128.8(6) . . ?
C9 C10 C11 106.5(5) . . ?
C12 C10 C11 124.7(6) . . ?
O3 C11 O2 120.4(6) . . ?
O3 C11 C10 129.8(6) . . ?
O2 C11 C10 109.8(5) . . ?
C13 C12 C17 117.7(6) . . ?
C13 C12 C10 120.6(6) . . ?
C17 C12 C10 121.6(6) . . ?
C14 C13 C12 121.6(6) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C13 120.0(6) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O4 C15 C14 125.4(6) . . ?
O4 C15 C16 114.6(6) . . ?
C14 C15 C16 120.0(6) . . ?
C17 C16 C15 119.2(6) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C12 121.5(6) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C2 O1 C1 O2 -93.7(6) . . . . ?
C2 O1 C1 C9 152.6(5) . . . . ?
C2 O1 C1 C4 23.7(6) . . . . ?
C11 O2 C1 O1 -116.3(5) . . . . ?
C11 O2 C1 C9 2.6(6) . . . . ?
C11 O2 C1 C4 129.0(6) . . . . ?
C1 O1 C2 C3 -4.0(7) . . . . ?
O1 C2 C3 C4 -17.0(7) . . . . ?
O1 C2 C3 C8 -141.0(6) . . . . ?
O1 C2 C3 C5 104.2(6) . . . . ?
O1 C1 C4 C3 -33.8(6) . . . . ?
O2 C1 C4 C3 83.1(6) . . . . ?
C9 C1 C4 C3 -159.0(5) . . . . ?
C2 C3 C4 C1 30.1(7) . . . . ?
C8 C3 C4 C1 153.2(5) . . . . ?
C5 C3 C4 C1 -92.9(6) . . . . ?
C2 C3 C5 C6 162.7(6) . . . . ?
C4 C3 C5 C6 -81.6(7) . . . . ?
C8 C3 C5 C6 40.8(7) . . . . ?
C3 C5 C6 C7 -28.2(7) . . . . ?
C5 C6 C7 C8 4.1(8) . . . . ?
C6 C7 C8 C3 21.6(8) . . . . ?
C2 C3 C8 C7 -161.1(6) . . . . ?
C4 C3 C8 C7 82.2(7) . . . . ?
C5 C3 C8 C7 -38.2(7) . . . . ?
O1 C1 C9 C10 116.0(6) . . . . ?
O2 C1 C9 C10 -0.8(7) . . . . ?
C4 C1 C9 C10 -122.0(6) . . . . ?
C1 C9 C10 C12 178.8(6) . . . . ?
C1 C9 C10 C11 -1.1(7) . . . . ?
C1 O2 C11 O3 178.9(6) . . . . ?
C1 O2 C11 C10 -3.4(7) . . . . ?
C9 C10 C11 O3 -179.8(7) . . . . ?
C12 C10 C11 O3 0.3(11) . . . . ?
C9 C10 C11 O2 2.8(7) . . . . ?
C12 C10 C11 O2 -177.1(6) . . . . ?
C9 C10 C12 C13 -2.9(10) . . . . ?
C11 C10 C12 C13 177.0(6) . . . . ?
C9 C10 C12 C17 179.7(6) . . . . ?
C11 C10 C12 C17 -0.4(10) . . . . ?
C17 C12 C13 C14 0.6(10) . . . . ?
C10 C12 C13 C14 -176.9(6) . . . . ?
C12 C13 C14 C15 0.2(10) . . . . ?
C18 O4 C15 C14 3.6(9) . . . . ?
C18 O4 C15 C16 -177.5(6) . . . . ?
C13 C14 C15 O4 177.4(6) . . . . ?
C13 C14 C15 C16 -1.5(9) . . . . ?
O4 C15 C16 C17 -177.1(6) . . . . ?
C14 C15 C16 C17 1.9(10) . . . . ?
C15 C16 C17 C12 -1.1(10) . . . . ?
C13 C12 C17 C16 -0.1(9) . . . . ?
C10 C12 C17 C16 177.3(6) . . . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.083



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-petroleum ether'
