# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_007_13133
_database_code_depnum_ccdc_archive 'CCDC 1041906'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 O4'
_chemical_formula_sum            'C17 H20 O4'
_chemical_formula_weight         288.33

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'

_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                   5.51640(10)
_cell_length_b                   11.8803(3)
_cell_length_c                   23.3669(16)
_cell_angle_alpha                94.989(7)
_cell_angle_beta                 90.739(6)
_cell_angle_gamma                98.520(7)
_cell_volume                     1508.23(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    16066
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      67.9

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.731
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'

_exptl_special_details           
; 
 'Rigaku MicroMax-007HF, Rigaku Saturn 944+ CCD' 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            54047
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.899
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             5407
_reflns_number_gt                4987
_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.7321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5407
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.36743(18) 0.82646(8) 0.30474(4) 0.0258(2) Uani 1 1 d . . . . .
C1 C 0.2150(3) 0.84569(11) 0.34745(6) 0.0222(3) Uani 1 1 d . . . . .
O2 O -0.00476(18) 0.83725(9) 0.34144(4) 0.0283(2) Uani 1 1 d . . . . .
C2 C 0.3569(3) 0.88300(12) 0.40401(6) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.5202 0.8562 0.4013 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2167(3) 0.82580(12) 0.45282(6) 0.0250(3) Uani 1 1 d . . . . .
H3A H 0.2890 0.8611 0.4903 0.030 Uiso 1 1 calc R U . . .
H3B H 0.0434 0.8383 0.4510 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2282(3) 0.69961(12) 0.44806(6) 0.0259(3) Uani 1 1 d . . . . .
H4 H 0.3766 0.6760 0.4600 0.031 Uiso 1 1 calc R U . . .
C5 C 0.0476(3) 0.61912(12) 0.42858(6) 0.0265(3) Uani 1 1 d . . . . .
H5 H -0.1054 0.6416 0.4194 0.032 Uiso 1 1 calc R U . . .
C6 C 0.0689(3) 0.49446(12) 0.42006(6) 0.0272(3) Uani 1 1 d . . . . .
H6A H -0.0763 0.4496 0.4360 0.033 Uiso 1 1 calc R U . . .
H6B H 0.2163 0.4802 0.4413 0.033 Uiso 1 1 calc R U . . .
C7 C 0.0876(3) 0.45464(12) 0.35606(6) 0.0260(3) Uani 1 1 d . . . . .
H7A H 0.0794 0.3705 0.3514 0.031 Uiso 1 1 calc R U . . .
H7B H -0.0525 0.4747 0.3342 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3239(3) 0.50982(12) 0.33246(6) 0.0250(3) Uani 1 1 d . . . . .
O3 O 0.28898(18) 0.56299(9) 0.28521(4) 0.0266(2) Uani 1 1 d . . . . .
O4 O 0.52412(19) 0.50754(10) 0.35340(5) 0.0376(3) Uani 1 1 d . . . . .
C9 C 0.5093(3) 0.62220(13) 0.26110(7) 0.0298(3) Uani 1 1 d . . . . .
H9A H 0.5992 0.5666 0.2396 0.036 Uiso 1 1 calc R U . . .
H9B H 0.6189 0.6644 0.2922 0.036 Uiso 1 1 calc R U . . .
C10 C 0.4295(3) 0.70448(13) 0.22119(6) 0.0308(3) Uani 1 1 d . . . . .
H10A H 0.3462 0.6603 0.1867 0.037 Uiso 1 1 calc R U . . .
H10B H 0.5765 0.7533 0.2084 0.037 Uiso 1 1 calc R U . . .
C11 C 0.2579(3) 0.78017(13) 0.24919(6) 0.0289(3) Uani 1 1 d . . . . .
H11A H 0.2376 0.8428 0.2251 0.035 Uiso 1 1 calc R U . . .
H11B H 0.0948 0.7351 0.2541 0.035 Uiso 1 1 calc R U . . .
C12 C 0.3984(3) 1.01291(12) 0.41077(6) 0.0216(3) Uani 1 1 d . . . . .
C13 C 0.2311(3) 1.07593(12) 0.43769(6) 0.0239(3) Uani 1 1 d . . . . .
H13 H 0.0906 1.0375 0.4547 0.029 Uiso 1 1 calc R U . . .
C14 C 0.2683(3) 1.19491(12) 0.43978(6) 0.0257(3) Uani 1 1 d . . . . .
H14 H 0.1542 1.2372 0.4585 0.031 Uiso 1 1 calc R U . . .
C15 C 0.4720(3) 1.25160(12) 0.41449(6) 0.0260(3) Uani 1 1 d . . . . .
H15 H 0.4966 1.3326 0.4153 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6391(3) 1.18920(13) 0.38805(6) 0.0268(3) Uani 1 1 d . . . . .
H16 H 0.7790 1.2277 0.3708 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6038(3) 1.07087(12) 0.38649(6) 0.0246(3) Uani 1 1 d . . . . .
H17 H 0.7209 1.0291 0.3687 0.030 Uiso 1 1 calc R U . . .
O5 O 0.97211(19) 0.01181(9) 0.19183(4) 0.0284(2) Uani 1 1 d . . . . .
C18 C 0.7874(3) -0.01017(12) 0.15353(6) 0.0254(3) Uani 1 1 d . . . . .
O6 O 0.5738(2) -0.01890(10) 0.16569(5) 0.0356(3) Uani 1 1 d . . . . .
C19 C 0.8843(3) -0.02285(13) 0.09292(6) 0.0277(3) Uani 1 1 d . . . . .
H19 H 1.0645 0.0056 0.0948 0.033 Uiso 1 1 calc R U . . .
C20 C 0.7597(3) 0.05412(13) 0.05608(6) 0.0301(3) Uani 1 1 d . . . . .
H20A H 0.7907 0.0349 0.0150 0.036 Uiso 1 1 calc R U . . .
H20B H 0.5803 0.0400 0.0614 0.036 Uiso 1 1 calc R U . . .
C21 C 0.8546(3) 0.17856(13) 0.07231(6) 0.0297(3) Uani 1 1 d . . . . .
H21 H 1.0123 0.2078 0.0595 0.036 Uiso 1 1 calc R U . . .
C22 C 0.7353(3) 0.24984(13) 0.10300(6) 0.0273(3) Uani 1 1 d . . . . .
H22 H 0.5778 0.2204 0.1159 0.033 Uiso 1 1 calc R U . . .
C23 C 0.8287(3) 0.37367(12) 0.11922(6) 0.0265(3) Uani 1 1 d . . . . .
H23A H 0.7009 0.4196 0.1093 0.032 Uiso 1 1 calc R U . . .
H23B H 0.9744 0.3970 0.0963 0.032 Uiso 1 1 calc R U . . .
C24 C 0.8982(3) 0.40017(12) 0.18345(6) 0.0255(3) Uani 1 1 d . . . . .
H24A H 0.9363 0.4839 0.1927 0.031 Uiso 1 1 calc R U . . .
H24B H 0.7581 0.3709 0.2068 0.031 Uiso 1 1 calc R U . . .
C25 C 1.1170(3) 0.34551(12) 0.19795(6) 0.0249(3) Uani 1 1 d . . . . .
O7 O 1.06778(18) 0.26985(9) 0.23755(4) 0.0270(2) Uani 1 1 d . . . . .
O8 O 1.31379(19) 0.36423(10) 0.17609(5) 0.0346(3) Uani 1 1 d . . . . .
C26 C 1.2599(3) 0.20239(13) 0.24878(7) 0.0292(3) Uani 1 1 d . . . . .
H26A H 1.3939 0.2494 0.2726 0.035 Uiso 1 1 calc R U . . .
H26B H 1.3288 0.1747 0.2122 0.035 Uiso 1 1 calc R U . . .
C27 C 1.1459(3) 0.10230(13) 0.28028(6) 0.0297(3) Uani 1 1 d . . . . .
H27A H 1.2657 0.0485 0.2829 0.036 Uiso 1 1 calc R U . . .
H27B H 1.1098 0.1305 0.3199 0.036 Uiso 1 1 calc R U . . .
C28 C 0.9120(3) 0.03889(13) 0.25127(6) 0.0279(3) Uani 1 1 d . . . . .
H28A H 0.8560 -0.0319 0.2698 0.033 Uiso 1 1 calc R U . . .
H28B H 0.7806 0.0874 0.2536 0.033 Uiso 1 1 calc R U . . .
C29 C 0.8472(3) -0.14875(12) 0.07151(6) 0.0264(3) Uani 1 1 d . . . . .
C30 C 0.6467(3) -0.20131(13) 0.03747(6) 0.0290(3) Uani 1 1 d . . . . .
H30 H 0.5239 -0.1581 0.0271 0.035 Uiso 1 1 calc R U . . .
C31 C 0.6247(3) -0.31632(13) 0.01859(7) 0.0322(3) Uani 1 1 d . . . . .
H31 H 0.4880 -0.3512 -0.0051 0.039 Uiso 1 1 calc R U . . .
C32 C 0.8010(3) -0.38060(13) 0.03403(7) 0.0338(4) Uani 1 1 d . . . . .
H32 H 0.7856 -0.4594 0.0210 0.041 Uiso 1 1 calc R U . . .
C33 C 0.9987(3) -0.32976(14) 0.06831(7) 0.0353(4) Uani 1 1 d . . . . .
H33 H 1.1190 -0.3739 0.0793 0.042 Uiso 1 1 calc R U . . .
C34 C 1.0231(3) -0.21485(14) 0.08684(7) 0.0317(3) Uani 1 1 d . . . . .
H34 H 1.1609 -0.1804 0.1102 0.038 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 1.3396(17) . ?
O1 C11 1.4525(17) . ?
C1 O2 1.2066(17) . ?
C1 C2 1.5248(19) . ?
C2 C12 1.5203(19) . ?
C2 C3 1.5371(19) . ?
C2 H2 1.0000 . ?
C3 C4 1.5044(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.321(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.499(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.538(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.504(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O4 1.2071(18) . ?
C8 O3 1.3442(18) . ?
O3 C9 1.4570(18) . ?
C9 C10 1.515(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.516(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.390(2) . ?
C12 C13 1.395(2) . ?
C13 C14 1.394(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O5 C18 1.3282(18) . ?
O5 C28 1.4521(17) . ?
C18 O6 1.2074(18) . ?
C18 C19 1.524(2) . ?
C19 C29 1.518(2) . ?
C19 C20 1.536(2) . ?
C19 H19 1.0000 . ?
C20 C21 1.507(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.318(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.499(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.538(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5010(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O8 1.2045(18) . ?
C25 O7 1.3480(18) . ?
O7 C26 1.4547(17) . ?
C26 C27 1.514(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.514(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.390(2) . ?
C29 C34 1.397(2) . ?
C30 C31 1.386(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.385(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.376(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(2) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

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 C11 117.34(11) . . ?
O2 C1 O1 124.28(13) . . ?
O2 C1 C2 124.76(13) . . ?
O1 C1 C2 110.93(12) . . ?
C12 C2 C1 107.29(11) . . ?
C12 C2 C3 115.09(11) . . ?
C1 C2 C3 109.07(11) . . ?
C12 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C4 C3 C2 110.71(12) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 124.99(14) . . ?
C5 C4 H4 117.5 . . ?
C3 C4 H4 117.5 . . ?
C4 C5 C6 124.12(14) . . ?
C4 C5 H5 117.9 . . ?
C6 C5 H5 117.9 . . ?
C5 C6 C7 111.45(12) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 110.73(12) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O4 C8 O3 123.14(14) . . ?
O4 C8 C7 124.20(13) . . ?
O3 C8 C7 112.66(12) . . ?
C8 O3 C9 115.80(11) . . ?
O3 C9 C10 107.50(12) . . ?
O3 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O3 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 C11 112.83(12) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
O1 C11 C10 107.07(12) . . ?
O1 C11 H11A 110.3 . . ?
C10 C11 H11A 110.3 . . ?
O1 C11 H11B 110.3 . . ?
C10 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
C17 C12 C13 118.83(13) . . ?
C17 C12 C2 118.73(12) . . ?
C13 C12 C2 122.34(12) . . ?
C14 C13 C12 120.53(13) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.02(13) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 119.51(13) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.54(13) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.54(13) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C18 O5 C28 117.23(11) . . ?
O6 C18 O5 124.18(13) . . ?
O6 C18 C19 125.48(13) . . ?
O5 C18 C19 110.34(12) . . ?
C29 C19 C18 108.84(12) . . ?
C29 C19 C20 115.39(12) . . ?
C18 C19 C20 107.94(12) . . ?
C29 C19 H19 108.2 . . ?
C18 C19 H19 108.2 . . ?
C20 C19 H19 108.2 . . ?
C21 C20 C19 111.13(12) . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 124.89(15) . . ?
C22 C21 H21 117.6 . . ?
C20 C21 H21 117.6 . . ?
C21 C22 C23 125.13(14) . . ?
C21 C22 H22 117.4 . . ?
C23 C22 H22 117.4 . . ?
C22 C23 C24 113.18(12) . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 110.23(12) . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
O8 C25 O7 123.10(13) . . ?
O8 C25 C24 124.54(13) . . ?
O7 C25 C24 112.35(12) . . ?
C25 O7 C26 115.93(11) . . ?
O7 C26 C27 107.48(12) . . ?
O7 C26 H26A 110.2 . . ?
C27 C26 H26A 110.2 . . ?
O7 C26 H26B 110.2 . . ?
C27 C26 H26B 110.2 . . ?
H26A C26 H26B 108.5 . . ?
C28 C27 C26 113.00(12) . . ?
C28 C27 H27A 109.0 . . ?
C26 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
O5 C28 C27 105.88(12) . . ?
O5 C28 H28A 110.6 . . ?
C27 C28 H28A 110.6 . . ?
O5 C28 H28B 110.6 . . ?
C27 C28 H28B 110.6 . . ?
H28A C28 H28B 108.7 . . ?
C30 C29 C34 118.49(14) . . ?
C30 C29 C19 123.16(14) . . ?
C34 C29 C19 118.35(13) . . ?
C31 C30 C29 120.49(14) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 120.31(15) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C33 C32 C31 119.69(15) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C34 120.32(15) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C33 C34 C29 120.70(14) . . ?
C33 C34 H34 119.7 . . ?
C29 C34 H34 119.7 . . ?

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
C11 O1 C1 O2 -7.2(2) . . . . ?
C11 O1 C1 C2 174.49(11) . . . . ?
O2 C1 C2 C12 -83.61(16) . . . . ?
O1 C1 C2 C12 94.67(13) . . . . ?
O2 C1 C2 C3 41.68(18) . . . . ?
O1 C1 C2 C3 -140.05(12) . . . . ?
C12 C2 C3 C4 -169.00(12) . . . . ?
C1 C2 C3 C4 70.39(15) . . . . ?
C2 C3 C4 C5 -103.29(17) . . . . ?
C3 C4 C5 C6 175.23(13) . . . . ?
C4 C5 C6 C7 -104.68(17) . . . . ?
C5 C6 C7 C8 66.57(16) . . . . ?
C6 C7 C8 O4 53.24(19) . . . . ?
C6 C7 C8 O3 -126.50(13) . . . . ?
O4 C8 O3 C9 -2.0(2) . . . . ?
C7 C8 O3 C9 177.79(11) . . . . ?
C8 O3 C9 C10 -162.90(12) . . . . ?
O3 C9 C10 C11 51.04(17) . . . . ?
C1 O1 C11 C10 -147.41(12) . . . . ?
C9 C10 C11 O1 48.19(17) . . . . ?
C1 C2 C12 C17 -87.24(15) . . . . ?
C3 C2 C12 C17 151.18(13) . . . . ?
C1 C2 C12 C13 89.15(15) . . . . ?
C3 C2 C12 C13 -32.43(18) . . . . ?
C17 C12 C13 C14 0.5(2) . . . . ?
C2 C12 C13 C14 -175.88(13) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C13 C14 C15 C16 -1.0(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C12 0.9(2) . . . . ?
C13 C12 C17 C16 -1.2(2) . . . . ?
C2 C12 C17 C16 175.29(12) . . . . ?
C28 O5 C18 O6 -6.8(2) . . . . ?
C28 O5 C18 C19 173.33(12) . . . . ?
O6 C18 C19 C29 -75.26(18) . . . . ?
O5 C18 C19 C29 104.56(14) . . . . ?
O6 C18 C19 C20 50.66(19) . . . . ?
O5 C18 C19 C20 -129.52(13) . . . . ?
C29 C19 C20 C21 -166.53(13) . . . . ?
C18 C19 C20 C21 71.51(16) . . . . ?
C19 C20 C21 C22 -103.95(18) . . . . ?
C20 C21 C22 C23 -179.93(14) . . . . ?
C21 C22 C23 C24 -108.87(17) . . . . ?
C22 C23 C24 C25 67.09(16) . . . . ?
C23 C24 C25 O8 58.90(19) . . . . ?
C23 C24 C25 O7 -119.48(13) . . . . ?
O8 C25 O7 C26 -5.9(2) . . . . ?
C24 C25 O7 C26 172.52(12) . . . . ?
C25 O7 C26 C27 -164.12(12) . . . . ?
O7 C26 C27 C28 49.67(16) . . . . ?
C18 O5 C28 C27 -158.91(12) . . . . ?
C26 C27 C28 O5 52.23(16) . . . . ?
C18 C19 C29 C30 96.09(16) . . . . ?
C20 C19 C29 C30 -25.4(2) . . . . ?
C18 C19 C29 C34 -83.88(17) . . . . ?
C20 C19 C29 C34 154.65(14) . . . . ?
C34 C29 C30 C31 -0.9(2) . . . . ?
C19 C29 C30 C31 179.10(14) . . . . ?
C29 C30 C31 C32 0.8(2) . . . . ?
C30 C31 C32 C33 0.0(2) . . . . ?
C31 C32 C33 C34 -0.7(2) . . . . ?
C32 C33 C34 C29 0.5(2) . . . . ?
C30 C29 C34 C33 0.3(2) . . . . ?
C19 C29 C34 C33 -179.73(14) . . . . ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_007-13159
_database_code_depnum_ccdc_archive 'CCDC 1041907'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_vrf_PLAT019_007-13159           
; 
PROBLEM: Check _diffrn_measured_fraction_theta_full/_max 
RESPONSE: Due to instrument limitations, a high resolution 
cutoff of 0.84 \%A was applied to the data. 
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 O4'
_chemical_formula_sum            'C23 H24 O4'
_chemical_formula_weight         364.42

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'

_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                   5.59160(10)
_cell_length_b                   11.9281(2)
_cell_length_c                   15.3677(11)
_cell_angle_alpha                70.326(5)
_cell_angle_beta                 80.097(6)
_cell_angle_gamma                79.031(6)
_cell_volume                     941.04(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    25939
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      66.7

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.701
_shelx_estimated_absorpt_T_min   0.833
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'

_exptl_special_details           
; 
 'Rigaku MicroMax-007HF, Rigaku Saturn 944+ CCD' 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            28626
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         66.499
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             3254
_reflns_number_gt                3006
_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 group.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+0.2939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3254
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_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 0.10427(13) 0.86590(7) 0.79947(5) 0.02322(18) Uani 1 1 d . . . . .
C1 C 0.30740(19) 0.89326(9) 0.74106(8) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.50504(14) 0.88448(7) 0.76624(5) 0.02537(19) Uani 1 1 d . . . . .
C2 C 0.2582(2) 0.94031(10) 0.63997(8) 0.0214(2) Uani 1 1 d . . . . .
H2 H 0.4191 0.9324 0.6008 0.026 Uiso 1 1 calc R U . . .
C3 C 0.0884(2) 0.87006(10) 0.61701(8) 0.0239(2) Uani 1 1 d . . . . .
H3A H -0.0743 0.8812 0.6529 0.029 Uiso 1 1 calc R U . . .
H3B H 0.0664 0.9063 0.5502 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1701(2) 0.73760(10) 0.63603(8) 0.0250(3) Uani 1 1 d . . . . .
H4 H 0.0624 0.6949 0.6221 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3728(2) 0.67249(10) 0.66972(8) 0.0240(2) Uani 1 1 d . . . . .
H5 H 0.4929 0.7127 0.6790 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4215(2) 0.53767(10) 0.69402(8) 0.0248(3) Uani 1 1 d . . . . .
H6A H 0.5947 0.5129 0.6727 0.030 Uiso 1 1 calc R U . . .
H6B H 0.3162 0.5113 0.6612 0.030 Uiso 1 1 calc R U . . .
C7 C 0.37019(19) 0.47562(10) 0.80014(8) 0.0206(2) Uani 1 1 d . . . . .
H7 H 0.4857 0.4987 0.8320 0.025 Uiso 1 1 calc R U . . .
C8 C 0.11026(19) 0.52457(9) 0.83093(8) 0.0210(2) Uani 1 1 d . . . . .
O3 O 0.10755(13) 0.58941(7) 0.88753(5) 0.02257(18) Uani 1 1 d . . . . .
O4 O -0.07227(14) 0.51175(7) 0.80551(6) 0.0297(2) Uani 1 1 d . . . . .
C9 C -0.12612(19) 0.66161(10) 0.90408(8) 0.0239(2) Uani 1 1 d . . . . .
H9A H -0.2441 0.6095 0.9463 0.029 Uiso 1 1 calc R U . . .
H9B H -0.1959 0.7049 0.8447 0.029 Uiso 1 1 calc R U . . .
C10 C -0.0784(2) 0.75030(10) 0.94775(8) 0.0256(3) Uani 1 1 d . . . . .
H10A H -0.2272 0.8102 0.9487 0.031 Uiso 1 1 calc R U . . .
H10B H -0.0475 0.7068 1.0130 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1368(2) 0.81565(11) 0.89732(8) 0.0252(3) Uani 1 1 d . . . . .
H11A H 0.1447 0.8806 0.9228 0.030 Uiso 1 1 calc R U . . .
H11B H 0.2919 0.7591 0.9056 0.030 Uiso 1 1 calc R U . . .
C12 C 0.1595(2) 1.07429(10) 0.61715(7) 0.0206(2) Uani 1 1 d . . . . .
C13 C -0.0784(2) 1.11374(10) 0.65082(8) 0.0234(2) Uani 1 1 d . . . . .
H13 H -0.1836 1.0567 0.6869 0.028 Uiso 1 1 calc R U . . .
C14 C -0.1624(2) 1.23564(11) 0.63200(8) 0.0264(3) Uani 1 1 d . . . . .
H14 H -0.3245 1.2616 0.6553 0.032 Uiso 1 1 calc R U . . .
C15 C -0.0105(2) 1.31993(10) 0.57927(8) 0.0271(3) Uani 1 1 d . . . . .
H15 H -0.0684 1.4034 0.5664 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2256(2) 1.28148(10) 0.54561(8) 0.0269(3) Uani 1 1 d . . . . .
H16 H 0.3301 1.3388 0.5094 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3102(2) 1.15944(10) 0.56464(8) 0.0233(2) Uani 1 1 d . . . . .
H17 H 0.4728 1.1338 0.5415 0.028 Uiso 1 1 calc R U . . .
C18 C 0.41021(19) 0.33969(10) 0.82441(7) 0.0197(2) Uani 1 1 d . . . . .
C19 C 0.6057(2) 0.27290(10) 0.87307(8) 0.0224(2) Uani 1 1 d . . . . .
H19 H 0.7095 0.3127 0.8920 0.027 Uiso 1 1 calc R U . . .
C20 C 0.6505(2) 0.14872(10) 0.89412(8) 0.0250(3) Uani 1 1 d . . . . .
H20 H 0.7848 0.1041 0.9272 0.030 Uiso 1 1 calc R U . . .
C21 C 0.5004(2) 0.08948(10) 0.86718(8) 0.0254(3) Uani 1 1 d . . . . .
H21 H 0.5308 0.0044 0.8818 0.030 Uiso 1 1 calc R U . . .
C22 C 0.3054(2) 0.15530(10) 0.81863(8) 0.0246(2) Uani 1 1 d . . . . .
H22 H 0.2018 0.1151 0.8000 0.030 Uiso 1 1 calc R U . . .
C23 C 0.26052(19) 0.27945(10) 0.79710(8) 0.0219(2) Uani 1 1 d . . . . .
H23 H 0.1269 0.3238 0.7635 0.026 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 1.3399(13) . ?
O1 C11 1.4489(13) . ?
C1 O2 1.2074(13) . ?
C1 C2 1.5183(15) . ?
C2 C12 1.5281(15) . ?
C2 C3 1.5316(15) . ?
C2 H2 1.0000 . ?
C3 C4 1.5002(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.3235(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.5046(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.5482(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C18 1.5171(15) . ?
C7 C8 1.5178(14) . ?
C7 H7 1.0000 . ?
C8 O4 1.2060(13) . ?
C8 O3 1.3413(13) . ?
O3 C9 1.4555(12) . ?
C9 C10 1.5127(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5119(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.3902(16) . ?
C12 C13 1.3958(15) . ?
C13 C14 1.3863(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3885(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3841(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3883(16) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.3921(15) . ?
C18 C23 1.3949(15) . ?
C19 C20 1.3877(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.3847(16) . ?
C20 H20 0.9500 . ?
C21 C22 1.3862(17) . ?
C21 H21 0.9500 . ?
C22 C23 1.3867(16) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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 C11 115.79(8) . . ?
O2 C1 O1 123.76(10) . . ?
O2 C1 C2 124.03(10) . . ?
O1 C1 C2 112.19(9) . . ?
C1 C2 C12 107.89(8) . . ?
C1 C2 C3 113.39(9) . . ?
C12 C2 C3 112.41(9) . . ?
C1 C2 H2 107.6 . . ?
C12 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
C4 C3 C2 116.62(9) . . ?
C4 C3 H3A 108.1 . . ?
C2 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C2 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
C5 C4 C3 128.41(11) . . ?
C5 C4 H4 115.8 . . ?
C3 C4 H4 115.8 . . ?
C4 C5 C6 122.96(11) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C5 C6 C7 111.47(9) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C18 C7 C8 112.53(9) . . ?
C18 C7 C6 111.54(9) . . ?
C8 C7 C6 107.36(9) . . ?
C18 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C6 C7 H7 108.4 . . ?
O4 C8 O3 123.40(10) . . ?
O4 C8 C7 125.07(10) . . ?
O3 C8 C7 111.47(9) . . ?
C8 O3 C9 115.30(8) . . ?
O3 C9 C10 107.43(9) . . ?
O3 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O3 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C11 C10 C9 113.47(9) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
O1 C11 C10 108.24(9) . . ?
O1 C11 H11A 110.1 . . ?
C10 C11 H11A 110.1 . . ?
O1 C11 H11B 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C17 C12 C13 118.76(10) . . ?
C17 C12 C2 120.00(10) . . ?
C13 C12 C2 121.20(10) . . ?
C14 C13 C12 120.46(11) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.31(11) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.56(11) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.20(11) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.71(10) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C19 C18 C23 118.76(10) . . ?
C19 C18 C7 119.33(9) . . ?
C23 C18 C7 121.89(10) . . ?
C20 C19 C18 120.58(10) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.34(10) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.46(10) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C23 120.42(10) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.45(10) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?

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
C11 O1 C1 O2 -4.28(15) . . . . ?
C11 O1 C1 C2 177.59(8) . . . . ?
O2 C1 C2 C12 -95.18(12) . . . . ?
O1 C1 C2 C12 82.93(11) . . . . ?
O2 C1 C2 C3 139.63(11) . . . . ?
O1 C1 C2 C3 -42.25(12) . . . . ?
C1 C2 C3 C4 -57.85(13) . . . . ?
C12 C2 C3 C4 179.43(9) . . . . ?
C2 C3 C4 C5 -0.61(18) . . . . ?
C3 C4 C5 C6 174.03(11) . . . . ?
C4 C5 C6 C7 -101.01(13) . . . . ?
C5 C6 C7 C18 177.89(9) . . . . ?
C5 C6 C7 C8 54.18(12) . . . . ?
C18 C7 C8 O4 -59.67(14) . . . . ?
C6 C7 C8 O4 63.43(14) . . . . ?
C18 C7 C8 O3 123.10(10) . . . . ?
C6 C7 C8 O3 -113.80(10) . . . . ?
O4 C8 O3 C9 -10.34(15) . . . . ?
C7 C8 O3 C9 166.94(9) . . . . ?
C8 O3 C9 C10 -165.89(9) . . . . ?
O3 C9 C10 C11 48.00(12) . . . . ?
C1 O1 C11 C10 -159.85(9) . . . . ?
C9 C10 C11 O1 51.31(12) . . . . ?
C1 C2 C12 C17 104.45(11) . . . . ?
C3 C2 C12 C17 -129.79(11) . . . . ?
C1 C2 C12 C13 -73.31(12) . . . . ?
C3 C2 C12 C13 52.45(13) . . . . ?
C17 C12 C13 C14 0.08(16) . . . . ?
C2 C12 C13 C14 177.87(10) . . . . ?
C12 C13 C14 C15 0.09(17) . . . . ?
C13 C14 C15 C16 -0.05(17) . . . . ?
C14 C15 C16 C17 -0.15(17) . . . . ?
C15 C16 C17 C12 0.32(17) . . . . ?
C13 C12 C17 C16 -0.29(16) . . . . ?
C2 C12 C17 C16 -178.10(10) . . . . ?
C8 C7 C18 C19 -127.68(11) . . . . ?
C6 C7 C18 C19 111.59(11) . . . . ?
C8 C7 C18 C23 54.15(14) . . . . ?
C6 C7 C18 C23 -66.58(13) . . . . ?
C23 C18 C19 C20 -0.11(16) . . . . ?
C7 C18 C19 C20 -178.34(10) . . . . ?
C18 C19 C20 C21 -0.21(17) . . . . ?
C19 C20 C21 C22 0.26(17) . . . . ?
C20 C21 C22 C23 0.01(17) . . . . ?
C21 C22 C23 C18 -0.33(17) . . . . ?
C19 C18 C23 C22 0.38(16) . . . . ?
C7 C18 C23 C22 178.56(10) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_spider-13132
_database_code_depnum_ccdc_archive 'CCDC 1041908'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 O4'
_chemical_formula_sum            'C23 H24 O4'
_chemical_formula_weight         364.42

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                   5.5848(4)
_cell_length_b                   11.7915(8)
_cell_length_c                   15.6064(11)
_cell_angle_alpha                69.615(5)
_cell_angle_beta                 84.229(6)
_cell_angle_gamma                81.837(6)
_cell_volume                     952.16(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9196
_cell_measurement_theta_min      3.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'

_exptl_special_details           
; 
 'Rigaku R-AXIS RAPID, Rigaku R_AXIS RAPID imaging plate' 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            16756
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.494
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_measurement_details      
;
scan:
	Number of images: 36
	           Slice: 20.0000 - 200.0000
	     Image width: 5.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 30
	           Slice: 20.0000 - 170.0000
	     Image width: 5.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 23
	           Slice: 21.0000 - 136.0000
	     Image width: 5.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: 0.0000
;
_reflns_number_total             4345
_reflns_number_gt                2226
_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0792P)²+0.2847P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4345
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1875
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.5166(3) 0.37148(18) 0.30969(12) 0.0439(5) Uani 1 1 d . . . . .
C1 C 0.6932(5) 0.4052(2) 0.24424(17) 0.0321(6) Uani 1 1 d . . . . .
O2 O 0.9019(3) 0.39884(18) 0.25913(13) 0.0438(5) Uani 1 1 d . . . . .
C2 C 0.5895(5) 0.4532(2) 0.14970(17) 0.0316(6) Uani 1 1 d . . . . .
H2 H 0.4326 0.4192 0.1544 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7678(5) 0.4057(2) 0.08467(17) 0.0358(6) Uani 1 1 d . . . . .
H3A H 0.7228 0.4490 0.0207 0.043 Uiso 1 1 calc R U . . .
H3B H 0.9335 0.4222 0.0900 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7640(5) 0.2716(2) 0.10742(17) 0.0364(6) Uani 1 1 d . . . . .
H4 H 0.6331 0.2459 0.0872 0.044 Uiso 1 1 calc R U . . .
C5 C 0.9294(5) 0.1865(2) 0.15353(17) 0.0353(6) Uani 1 1 d . . . . .
H5 H 1.0663 0.2125 0.1698 0.042 Uiso 1 1 calc R U . . .
C6 C 0.9174(5) 0.0527(2) 0.18211(18) 0.0357(6) Uani 1 1 d . . . . .
H6A H 1.0746 0.0128 0.1656 0.043 Uiso 1 1 calc R U . . .
H6B H 0.7911 0.0376 0.1485 0.043 Uiso 1 1 calc R U . . .
C7 C 0.8588(5) -0.0046(2) 0.28683(17) 0.0313(6) Uani 1 1 d . . . . .
H7 H 0.9753 0.0201 0.3199 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6054(5) 0.0450(2) 0.30982(18) 0.0348(6) Uani 1 1 d . . . . .
O3 O 0.5977(3) 0.08701(18) 0.37976(12) 0.0408(5) Uani 1 1 d . . . . .
O4 O 0.4275(4) 0.04754(19) 0.27068(15) 0.0487(6) Uani 1 1 d . . . . .
C9 C 0.3635(5) 0.1442(3) 0.4031(2) 0.0434(7) Uani 1 1 d . . . . .
H9A H 0.2617 0.0814 0.4422 0.052 Uiso 1 1 calc R U . . .
H9B H 0.2781 0.1920 0.3468 0.052 Uiso 1 1 calc R U . . .
C10 C 0.4085(6) 0.2264(3) 0.45348(19) 0.0447(8) Uani 1 1 d . . . . .
H10A H 0.4685 0.1759 0.5142 0.054 Uiso 1 1 calc R U . . .
H10B H 0.2534 0.2735 0.4635 0.054 Uiso 1 1 calc R U . . .
C11 C 0.5900(6) 0.3140(3) 0.40283(17) 0.0463(8) Uani 1 1 d . . . . .
H11A H 0.5916 0.3760 0.4321 0.056 Uiso 1 1 calc R U . . .
H11B H 0.7546 0.2696 0.4036 0.056 Uiso 1 1 calc R U . . .
C12 C 0.5379(5) 0.5906(2) 0.12236(16) 0.0309(6) Uani 1 1 d . . . . .
C13 C 0.3145(5) 0.6402(3) 0.15036(18) 0.0371(7) Uani 1 1 d . . . . .
H13 H 0.1972 0.5880 0.1839 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2631(5) 0.7650(3) 0.12946(19) 0.0391(7) Uani 1 1 d . . . . .
H14 H 0.1116 0.7980 0.1494 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4311(5) 0.8416(3) 0.07971(19) 0.0403(7) Uani 1 1 d . . . . .
H15 H 0.3946 0.9272 0.0650 0.048 Uiso 1 1 calc R U . . .
C16 C 0.6528(5) 0.7936(2) 0.05129(19) 0.0389(7) Uani 1 1 d . . . . .
H16 H 0.7690 0.8462 0.0173 0.047 Uiso 1 1 calc R U . . .
C17 C 0.7048(5) 0.6688(2) 0.07251(17) 0.0356(6) Uani 1 1 d . . . . .
H17 H 0.8569 0.6363 0.0526 0.043 Uiso 1 1 calc R U . . .
C18 C 0.8855(5) -0.1421(2) 0.31723(16) 0.0303(6) Uani 1 1 d . . . . .
C19 C 0.7252(5) -0.2053(2) 0.29415(17) 0.0345(6) Uani 1 1 d . . . . .
H19 H 0.5891 -0.1615 0.2604 0.041 Uiso 1 1 calc R U . . .
C20 C 0.7601(5) -0.3305(3) 0.31943(19) 0.0404(7) Uani 1 1 d . . . . .
H20 H 0.6479 -0.3720 0.3031 0.048 Uiso 1 1 calc R U . . .
C21 C 0.9574(5) -0.3962(3) 0.36844(19) 0.0420(7) Uani 1 1 d . . . . .
H21 H 0.9817 -0.4824 0.3855 0.050 Uiso 1 1 calc R U . . .
C22 C 1.1177(5) -0.3355(3) 0.39212(19) 0.0420(7) Uani 1 1 d . . . . .
H22 H 1.2536 -0.3800 0.4258 0.050 Uiso 1 1 calc R U . . .
C23 C 1.0826(5) -0.2093(2) 0.36719(18) 0.0357(6) Uani 1 1 d . . . . .
H23 H 1.1943 -0.1685 0.3844 0.043 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 1.342(3) . ?
O1 C11 1.447(3) . ?
C1 O2 1.198(3) . ?
C1 C2 1.526(3) . ?
C2 C12 1.517(4) . ?
C2 C3 1.540(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.497(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.321(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.493(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.556(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C18 1.511(4) . ?
C7 C8 1.511(4) . ?
C7 H7 1.0000 . ?
C8 O4 1.209(3) . ?
C8 O3 1.342(3) . ?
O3 C9 1.457(3) . ?
C9 C10 1.503(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.512(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.386(4) . ?
C12 C13 1.396(4) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.388(4) . ?
C18 C23 1.394(4) . ?
C19 C20 1.380(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.372(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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 C11 116.8(2) . . ?
O2 C1 O1 124.1(2) . . ?
O2 C1 C2 125.5(2) . . ?
O1 C1 C2 110.4(2) . . ?
C12 C2 C1 107.8(2) . . ?
C12 C2 C3 115.7(2) . . ?
C1 C2 C3 108.1(2) . . ?
C12 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C4 C3 C2 110.6(2) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 124.8(3) . . ?
C5 C4 H4 117.6 . . ?
C3 C4 H4 117.6 . . ?
C4 C5 C6 125.0(3) . . ?
C4 C5 H5 117.5 . . ?
C6 C5 H5 117.5 . . ?
C5 C6 C7 111.9(2) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C18 C7 C8 111.0(2) . . ?
C18 C7 C6 111.4(2) . . ?
C8 C7 C6 109.0(2) . . ?
C18 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C6 C7 H7 108.4 . . ?
O4 C8 O3 122.8(2) . . ?
O4 C8 C7 124.9(3) . . ?
O3 C8 C7 112.2(2) . . ?
C8 O3 C9 116.3(2) . . ?
O3 C9 C10 107.8(2) . . ?
O3 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O3 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 C11 112.9(2) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
O1 C11 C10 107.2(2) . . ?
O1 C11 H11A 110.3 . . ?
C10 C11 H11A 110.3 . . ?
O1 C11 H11B 110.3 . . ?
C10 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C17 C12 C13 118.7(2) . . ?
C17 C12 C2 122.8(2) . . ?
C13 C12 C2 118.5(2) . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 120.9(2) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C19 C18 C23 117.8(2) . . ?
C19 C18 C7 122.4(2) . . ?
C23 C18 C7 119.7(2) . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.8(3) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?

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
C11 O1 C1 O2 -5.8(4) . . . . ?
C11 O1 C1 C2 174.8(2) . . . . ?
O2 C1 C2 C12 -84.9(3) . . . . ?
O1 C1 C2 C12 94.4(2) . . . . ?
O2 C1 C2 C3 40.8(3) . . . . ?
O1 C1 C2 C3 -139.8(2) . . . . ?
C12 C2 C3 C4 -168.1(2) . . . . ?
C1 C2 C3 C4 71.0(3) . . . . ?
C2 C3 C4 C5 -101.8(3) . . . . ?
C3 C4 C5 C6 175.4(2) . . . . ?
C4 C5 C6 C7 -107.0(3) . . . . ?
C5 C6 C7 C18 -171.2(2) . . . . ?
C5 C6 C7 C8 66.0(3) . . . . ?
C18 C7 C8 O4 -72.9(3) . . . . ?
C6 C7 C8 O4 50.2(3) . . . . ?
C18 C7 C8 O3 107.1(2) . . . . ?
C6 C7 C8 O3 -129.8(2) . . . . ?
O4 C8 O3 C9 -3.9(4) . . . . ?
C7 C8 O3 C9 176.0(2) . . . . ?
C8 O3 C9 C10 -157.9(2) . . . . ?
O3 C9 C10 C11 52.1(3) . . . . ?
C1 O1 C11 C10 -149.5(2) . . . . ?
C9 C10 C11 O1 49.4(3) . . . . ?
C1 C2 C12 C17 91.9(3) . . . . ?
C3 C2 C12 C17 -29.1(4) . . . . ?
C1 C2 C12 C13 -86.6(3) . . . . ?
C3 C2 C12 C13 152.3(2) . . . . ?
C17 C12 C13 C14 -0.8(4) . . . . ?
C2 C12 C13 C14 177.9(2) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C12 -0.3(4) . . . . ?
C13 C12 C17 C16 0.5(4) . . . . ?
C2 C12 C17 C16 -178.1(2) . . . . ?
C8 C7 C18 C19 51.3(3) . . . . ?
C6 C7 C18 C19 -70.4(3) . . . . ?
C8 C7 C18 C23 -131.4(3) . . . . ?
C6 C7 C18 C23 106.9(3) . . . . ?
C23 C18 C19 C20 -0.3(4) . . . . ?
C7 C18 C19 C20 177.1(2) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C18 -0.5(4) . . . . ?
C19 C18 C23 C22 0.6(4) . . . . ?
C7 C18 C23 C22 -176.8(2) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-3

