# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008



data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Frederick West'
_publ_contact_author_email       FREDERICK.WEST@UALBERTA.CA

_publ_section_title              
;
Cyclooctatrienes from pyran-2-ones via a tandem
[4+4]-photocycloaddition/decarboxylation process
;
loop_
_publ_author_name
'Frederick West'
'Charles E Chase'
'Lei Li.'

# Attachment 'FGW0803.CIF'

data_3i(syn)
_database_code_depnum_ccdc_archive 'CCDC 690017'

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 O5'
_chemical_formula_sum            'C16 H18 O5'
_chemical_formula_weight         290.30

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pn
_symmetry_space_group_name_Hall  'P -2yac'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   10.7376(13)
_cell_length_b                   8.3473(10)
_cell_length_c                   16.1039(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.648(2)
_cell_angle_gamma                90.00
_cell_volume                     1427.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4802
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      23.79

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      193(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 PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12166
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.53
_reflns_number_total             6533
_reflns_number_gt                5088
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1066P)^2^+0.2782P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881. 3245 Friedel pairs.'
_refine_ls_abs_structure_Flack   -0.3(12)
_refine_ls_number_reflns         6533
_refine_ls_number_parameters     381
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1775
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O -0.0546(2) 0.4330(3) 0.85398(14) 0.0293(5) Uani 1 1 d . . .
O2A O 0.1700(2) 0.4520(3) 0.81950(15) 0.0322(5) Uani 1 1 d . . .
O3A O 0.1575(2) 0.1888(3) 0.80643(17) 0.0390(6) Uani 1 1 d . . .
O4A O -0.0044(3) 0.4527(3) 0.57842(15) 0.0369(6) Uani 1 1 d . . .
O5A O 0.0479(3) 0.6973(3) 0.53396(19) 0.0574(9) Uani 1 1 d . . .
C1A C -0.0532(3) 0.1901(4) 0.6712(2) 0.0301(7) Uani 1 1 d . . .
H1A H -0.1205 0.2231 0.6245 0.036 Uiso 1 1 calc R . .
C2A C -0.1186(4) 0.1003(4) 0.7348(2) 0.0325(7) Uani 1 1 d . . .
H2AA H -0.0564 0.0484 0.7781 0.039 Uiso 1 1 calc R . .
H2BA H -0.1763 0.0175 0.7068 0.039 Uiso 1 1 calc R . .
C3A C -0.1924(3) 0.2320(4) 0.7739(2) 0.0311(7) Uani 1 1 d . . .
H3AA H -0.2777 0.2445 0.7414 0.037 Uiso 1 1 calc R . .
H3BA H -0.2006 0.2047 0.8326 0.037 Uiso 1 1 calc R . .
C4A C -0.1162(3) 0.3867(4) 0.77071(19) 0.0254(7) Uani 1 1 d . . .
C5A C -0.1872(3) 0.5357(4) 0.7424(2) 0.0349(8) Uani 1 1 d . . .
H5A H -0.2598 0.5407 0.7008 0.042 Uiso 1 1 calc R . .
C6A C -0.1328(4) 0.6598(4) 0.7846(2) 0.0371(8) Uani 1 1 d . . .
H6A H -0.1599 0.7681 0.7798 0.045 Uiso 1 1 calc R . .
C7A C -0.0200(3) 0.5962(4) 0.8416(2) 0.0327(7) Uani 1 1 d . . .
H7A H -0.0066 0.6558 0.8961 0.039 Uiso 1 1 calc R . .
C8A C 0.1016(4) 0.6023(4) 0.7977(2) 0.0339(8) Uani 1 1 d . . .
C9A C 0.0771(4) 0.6129(4) 0.7027(2) 0.0326(7) Uani 1 1 d . . .
H9A H 0.0960 0.7062 0.6732 0.039 Uiso 1 1 calc R . .
C10A C 0.0275(3) 0.4834(4) 0.6638(2) 0.0296(7) Uani 1 1 d . . .
C11A C -0.0047(3) 0.3438(4) 0.7170(2) 0.0252(6) Uani 1 1 d . . .
C12A C 0.1117(3) 0.3172(4) 0.7848(2) 0.0283(7) Uani 1 1 d . . .
C13A C 0.0411(4) 0.0892(4) 0.6314(3) 0.0416(9) Uani 1 1 d . . .
H13A H -0.0017 -0.0047 0.6040 0.050 Uiso 1 1 calc R . .
H13B H 0.1092 0.0541 0.6751 0.050 Uiso 1 1 calc R . .
H13C H 0.0764 0.1535 0.5897 0.050 Uiso 1 1 calc R . .
C14A C 0.1889(4) 0.7368(5) 0.8351(2) 0.0431(9) Uani 1 1 d . . .
H14A H 0.2638 0.7397 0.8071 0.052 Uiso 1 1 calc R . .
H14B H 0.2145 0.7175 0.8953 0.052 Uiso 1 1 calc R . .
H14C H 0.1446 0.8395 0.8270 0.052 Uiso 1 1 calc R . .
C15A C 0.0104(3) 0.5652(4) 0.5188(2) 0.0353(8) Uani 1 1 d . . .
C16A C -0.0275(5) 0.4980(5) 0.4335(3) 0.0556(12) Uani 1 1 d . . .
H16A H -0.0648 0.5828 0.3956 0.067 Uiso 1 1 calc R . .
H16B H -0.0894 0.4126 0.4359 0.067 Uiso 1 1 calc R . .
H16C H 0.0467 0.4543 0.4128 0.067 Uiso 1 1 calc R . .
O1B O 0.4490(2) 0.0614(3) 0.45362(14) 0.0301(5) Uani 1 1 d . . .
O2B O 0.6621(2) 0.0801(3) 0.54687(15) 0.0314(5) Uani 1 1 d . . .
O3B O 0.6220(2) 0.3383(3) 0.55724(18) 0.0394(6) Uani 1 1 d . . .
O4B O 0.4590(3) 0.0449(3) 0.73682(15) 0.0368(6) Uani 1 1 d . . .
O5B O 0.5487(5) -0.1699(5) 0.8037(2) 0.0954(16) Uani 1 1 d . . .
C1B C 0.3916(3) 0.2961(4) 0.6299(2) 0.0305(7) Uani 1 1 d . . .
H1B H 0.3216 0.2479 0.6560 0.037 Uiso 1 1 calc R . .
C2B C 0.3303(4) 0.3765(4) 0.5480(2) 0.0361(8) Uani 1 1 d . . .
H2AB H 0.2599 0.4468 0.5582 0.043 Uiso 1 1 calc R . .
H2BB H 0.3927 0.4411 0.5231 0.043 Uiso 1 1 calc R . .
C3B C 0.2828(3) 0.2384(4) 0.4910(2) 0.0338(7) Uani 1 1 d . . .
H3AB H 0.2845 0.2673 0.4316 0.041 Uiso 1 1 calc R . .
H3BB H 0.1952 0.2112 0.4978 0.041 Uiso 1 1 calc R . .
C4B C 0.3703(3) 0.0958(4) 0.5164(2) 0.0280(7) Uani 1 1 d . . .
C5B C 0.3115(4) -0.0661(4) 0.5277(2) 0.0355(8) Uani 1 1 d . . .
H5B H 0.2352 -0.0845 0.5493 0.043 Uiso 1 1 calc R . .
C6B C 0.3844(4) -0.1767(4) 0.5024(2) 0.0389(8) Uani 1 1 d . . .
H6B H 0.3686 -0.2888 0.5011 0.047 Uiso 1 1 calc R . .
C7B C 0.4979(4) -0.0950(4) 0.4756(2) 0.0338(8) Uani 1 1 d . . .
H7B H 0.5257 -0.1502 0.4264 0.041 Uiso 1 1 calc R . .
C8B C 0.6085(4) -0.0815(4) 0.5513(2) 0.0332(8) Uani 1 1 d . . .
C9B C 0.5707(4) -0.0985(4) 0.6377(2) 0.0330(8) Uani 1 1 d . . .
H9B H 0.5943 -0.1883 0.6728 0.040 Uiso 1 1 calc R . .
C10B C 0.5016(3) 0.0218(4) 0.6612(2) 0.0291(7) Uani 1 1 d . . .
C11B C 0.4649(3) 0.1554(4) 0.5986(2) 0.0265(7) Uani 1 1 d . . .
C12B C 0.5876(3) 0.2022(4) 0.5651(2) 0.0305(7) Uani 1 1 d . . .
C13B C 0.4609(4) 0.4109(5) 0.6948(3) 0.0451(10) Uani 1 1 d . . .
H13D H 0.4965 0.3508 0.7451 0.054 Uiso 1 1 calc R . .
H13E H 0.4018 0.4915 0.7099 0.054 Uiso 1 1 calc R . .
H13F H 0.5289 0.4643 0.6712 0.054 Uiso 1 1 calc R . .
C14B C 0.7133(4) -0.1966(5) 0.5382(2) 0.0438(9) Uani 1 1 d . . .
H14D H 0.7818 -0.1885 0.5857 0.053 Uiso 1 1 calc R . .
H14E H 0.7453 -0.1692 0.4861 0.053 Uiso 1 1 calc R . .
H14F H 0.6806 -0.3063 0.5344 0.053 Uiso 1 1 calc R . .
C15B C 0.4929(4) -0.0482(5) 0.8060(2) 0.0400(9) Uani 1 1 d . . .
C16B C 0.4464(4) 0.0216(5) 0.8793(2) 0.0412(9) Uani 1 1 d . . .
H16D H 0.4351 -0.0635 0.9195 0.049 Uiso 1 1 calc R . .
H16E H 0.3656 0.0749 0.8612 0.049 Uiso 1 1 calc R . .
H16F H 0.5076 0.0999 0.9062 0.049 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.0435(13) 0.0199(11) 0.0244(11) 0.0019(9) 0.0047(10) -0.0023(10)
O2A 0.0368(12) 0.0241(11) 0.0346(13) -0.0003(10) 0.0018(10) -0.0021(10)
O3A 0.0472(15) 0.0247(12) 0.0441(14) 0.0014(10) 0.0037(11) 0.0082(11)
O4A 0.0576(16) 0.0246(12) 0.0284(12) 0.0038(10) 0.0057(11) -0.0128(11)
O5A 0.099(2) 0.0278(14) 0.0408(15) 0.0108(11) -0.0032(15) -0.0183(15)
C1A 0.0398(18) 0.0202(15) 0.0303(17) -0.0036(13) 0.0050(14) -0.0040(13)
C2A 0.0441(19) 0.0158(15) 0.0371(18) 0.0058(13) 0.0047(15) -0.0055(14)
C3A 0.0350(17) 0.0245(16) 0.0343(17) 0.0011(13) 0.0069(14) -0.0060(14)
C4A 0.0308(16) 0.0190(15) 0.0256(15) 0.0051(12) 0.0017(13) 0.0019(12)
C5A 0.0350(18) 0.0250(17) 0.044(2) 0.0070(14) 0.0029(15) 0.0059(15)
C6A 0.046(2) 0.0221(16) 0.043(2) -0.0009(15) 0.0079(16) 0.0047(15)
C7A 0.048(2) 0.0169(15) 0.0335(17) -0.0037(13) 0.0072(15) -0.0014(14)
C8A 0.0435(19) 0.0207(16) 0.0358(18) -0.0009(13) 0.0002(15) -0.0045(15)
C9A 0.045(2) 0.0247(16) 0.0276(16) 0.0006(13) 0.0053(14) -0.0099(15)
C10A 0.0409(19) 0.0185(15) 0.0293(17) 0.0028(13) 0.0049(14) -0.0043(14)
C11A 0.0348(17) 0.0173(14) 0.0241(14) 0.0019(12) 0.0061(13) -0.0041(12)
C12A 0.0326(17) 0.0258(16) 0.0272(16) 0.0041(13) 0.0072(13) -0.0006(13)
C13A 0.059(2) 0.0243(18) 0.044(2) -0.0115(15) 0.0164(18) -0.0056(17)
C14A 0.057(2) 0.0317(19) 0.039(2) -0.0056(16) 0.0012(17) -0.0136(18)
C15A 0.0422(19) 0.0316(19) 0.0318(18) 0.0097(15) 0.0043(15) 0.0014(15)
C16A 0.090(3) 0.045(2) 0.028(2) 0.0033(17) -0.004(2) -0.009(2)
O1B 0.0401(13) 0.0249(11) 0.0257(11) 0.0014(9) 0.0063(9) -0.0001(10)
O2B 0.0362(12) 0.0227(11) 0.0364(13) 0.0004(10) 0.0093(10) 0.0001(9)
O3B 0.0421(14) 0.0248(13) 0.0511(15) 0.0043(11) 0.0066(12) -0.0058(11)
O4B 0.0544(15) 0.0307(13) 0.0251(12) 0.0013(10) 0.0058(10) 0.0127(12)
O5B 0.171(4) 0.075(3) 0.0487(19) 0.0297(18) 0.046(2) 0.071(3)
C1B 0.0353(18) 0.0218(16) 0.0340(17) -0.0002(13) 0.0036(14) 0.0027(13)
C2B 0.0391(19) 0.0243(17) 0.045(2) 0.0056(15) 0.0070(16) 0.0065(14)
C3B 0.0361(18) 0.0337(18) 0.0307(17) 0.0084(15) 0.0022(14) 0.0008(15)
C4B 0.0369(17) 0.0220(15) 0.0245(15) 0.0019(12) 0.0024(13) -0.0023(13)
C5B 0.0421(19) 0.0316(18) 0.0334(18) 0.0001(14) 0.0072(15) -0.0106(16)
C6B 0.056(2) 0.0218(16) 0.0378(19) -0.0062(14) 0.0030(17) -0.0058(16)
C7B 0.054(2) 0.0207(16) 0.0277(17) -0.0061(13) 0.0083(15) 0.0025(14)
C8B 0.049(2) 0.0203(16) 0.0315(17) 0.0003(13) 0.0093(15) 0.0016(14)
C9B 0.050(2) 0.0220(16) 0.0272(16) 0.0061(13) 0.0074(15) 0.0065(15)
C10B 0.0441(19) 0.0197(15) 0.0229(15) 0.0009(12) 0.0026(13) -0.0010(13)
C11B 0.0351(17) 0.0168(14) 0.0272(15) -0.0013(12) 0.0032(13) 0.0008(13)
C12B 0.0357(18) 0.0236(16) 0.0303(17) 0.0030(13) -0.0015(14) -0.0010(14)
C13B 0.051(2) 0.0267(19) 0.056(2) -0.0158(17) 0.0028(19) 0.0071(17)
C14B 0.064(3) 0.0310(19) 0.040(2) -0.0003(15) 0.0174(19) 0.0137(18)
C15B 0.054(2) 0.036(2) 0.0301(18) 0.0069(16) 0.0053(16) 0.0075(18)
C16B 0.054(2) 0.037(2) 0.0308(18) -0.0023(16) 0.0012(16) 0.0024(18)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C7A 1.433(4) . ?
O1A C4A 1.455(4) . ?
O2A C12A 1.366(4) . ?
O2A C8A 1.469(4) . ?
O3A C12A 1.208(4) . ?
O4A C15A 1.369(4) . ?
O4A C10A 1.391(4) . ?
O5A C15A 1.186(5) . ?
C1A C2A 1.524(5) . ?
C1A C13A 1.530(5) . ?
C1A C11A 1.531(4) . ?
C2A C3A 1.543(5) . ?
C3A C4A 1.533(5) . ?
C4A C5A 1.494(4) . ?
C4A C11A 1.619(5) . ?
C5A C6A 1.325(5) . ?
C6A C7A 1.502(5) . ?
C7A C8A 1.577(5) . ?
C8A C9A 1.516(5) . ?
C8A C14A 1.528(5) . ?
C9A C10A 1.320(5) . ?
C10A C11A 1.516(4) . ?
C11A C12A 1.548(5) . ?
C15A C16A 1.482(5) . ?
O1B C7B 1.432(4) . ?
O1B C4B 1.441(4) . ?
O2B C12B 1.355(4) . ?
O2B C8B 1.472(4) . ?
O3B C12B 1.208(4) . ?
O4B C15B 1.363(4) . ?
O4B C10B 1.378(4) . ?
O5B C15B 1.183(5) . ?
C1B C13B 1.527(5) . ?
C1B C2B 1.537(5) . ?
C1B C11B 1.540(4) . ?
C2B C3B 1.513(5) . ?
C3B C4B 1.533(5) . ?
C4B C5B 1.514(5) . ?
C4B C11B 1.621(4) . ?
C5B C6B 1.315(5) . ?
C6B C7B 1.515(5) . ?
C7B C8B 1.572(5) . ?
C8B C9B 1.515(5) . ?
C8B C14B 1.518(5) . ?
C9B C10B 1.336(5) . ?
C10B C11B 1.515(4) . ?
C11B C12B 1.547(5) . ?
C15B C16B 1.469(5) . ?

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
C7A O1A C4A 102.5(2) . . ?
C12A O2A C8A 115.1(2) . . ?
C15A O4A C10A 122.0(3) . . ?
C2A C1A C13A 114.3(3) . . ?
C2A C1A C11A 104.2(3) . . ?
C13A C1A C11A 117.7(3) . . ?
C1A C2A C3A 103.9(3) . . ?
C4A C3A C2A 106.1(3) . . ?
O1A C4A C5A 101.5(3) . . ?
O1A C4A C3A 111.4(2) . . ?
C5A C4A C3A 117.5(3) . . ?
O1A C4A C11A 106.3(2) . . ?
C5A C4A C11A 113.9(3) . . ?
C3A C4A C11A 105.8(2) . . ?
C6A C5A C4A 109.2(3) . . ?
C5A C6A C7A 106.8(3) . . ?
O1A C7A C6A 102.6(3) . . ?
O1A C7A C8A 110.0(3) . . ?
C6A C7A C8A 111.1(3) . . ?
O2A C8A C9A 107.2(3) . . ?
O2A C8A C14A 106.2(3) . . ?
C9A C8A C14A 111.0(3) . . ?
O2A C8A C7A 106.5(3) . . ?
C9A C8A C7A 115.1(3) . . ?
C14A C8A C7A 110.3(3) . . ?
C10A C9A C8A 115.3(3) . . ?
C9A C10A O4A 129.9(3) . . ?
C9A C10A C11A 118.2(3) . . ?
O4A C10A C11A 111.9(3) . . ?
C10A C11A C1A 117.5(3) . . ?
C10A C11A C12A 106.3(3) . . ?
C1A C11A C12A 113.5(3) . . ?
C10A C11A C4A 112.5(3) . . ?
C1A C11A C4A 102.6(2) . . ?
C12A C11A C4A 103.8(2) . . ?
O3A C12A O2A 118.1(3) . . ?
O3A C12A C11A 125.5(3) . . ?
O2A C12A C11A 116.2(3) . . ?
O5A C15A O4A 124.4(3) . . ?
O5A C15A C16A 125.4(4) . . ?
O4A C15A C16A 110.2(3) . . ?
C7B O1B C4B 103.9(2) . . ?
C12B O2B C8B 115.5(3) . . ?
C15B O4B C10B 124.1(3) . . ?
C13B C1B C2B 114.6(3) . . ?
C13B C1B C11B 118.9(3) . . ?
C2B C1B C11B 103.1(3) . . ?
C3B C2B C1B 104.4(3) . . ?
C2B C3B C4B 107.0(3) . . ?
O1B C4B C5B 101.9(3) . . ?
O1B C4B C3B 111.6(3) . . ?
C5B C4B C3B 118.4(3) . . ?
O1B C4B C11B 105.8(2) . . ?
C5B C4B C11B 113.4(3) . . ?
C3B C4B C11B 105.3(3) . . ?
C6B C5B C4B 108.1(3) . . ?
C5B C6B C7B 108.3(3) . . ?
O1B C7B C6B 101.6(3) . . ?
O1B C7B C8B 109.4(3) . . ?
C6B C7B C8B 111.0(3) . . ?
O2B C8B C9B 106.9(3) . . ?
O2B C8B C14B 105.6(3) . . ?
C9B C8B C14B 112.0(3) . . ?
O2B C8B C7B 106.5(3) . . ?
C9B C8B C7B 115.5(3) . . ?
C14B C8B C7B 109.7(3) . . ?
C10B C9B C8B 115.2(3) . . ?
C9B C10B O4B 128.8(3) . . ?
C9B C10B C11B 117.8(3) . . ?
O4B C10B C11B 113.4(3) . . ?
C10B C11B C1B 116.1(3) . . ?
C10B C11B C12B 105.5(3) . . ?
C1B C11B C12B 115.2(3) . . ?
C10B C11B C4B 112.7(2) . . ?
C1B C11B C4B 102.3(2) . . ?
C12B C11B C4B 104.8(2) . . ?
O3B C12B O2B 119.0(3) . . ?
O3B C12B C11B 124.4(3) . . ?
O2B C12B C11B 116.6(3) . . ?
O5B C15B O4B 122.6(4) . . ?
O5B C15B C16B 126.9(4) . . ?
O4B C15B C16B 110.5(3) . . ?

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
C13A C1A C2A C3A 172.3(3) . . . . ?
C11A C1A C2A C3A 42.5(3) . . . . ?
C1A C2A C3A C4A -30.3(3) . . . . ?
C7A O1A C4A C5A -38.8(3) . . . . ?
C7A O1A C4A C3A -164.6(3) . . . . ?
C7A O1A C4A C11A 80.6(3) . . . . ?
C2A C3A C4A O1A -107.8(3) . . . . ?
C2A C3A C4A C5A 135.7(3) . . . . ?
C2A C3A C4A C11A 7.3(3) . . . . ?
O1A C4A C5A C6A 23.2(4) . . . . ?
C3A C4A C5A C6A 144.9(3) . . . . ?
C11A C4A C5A C6A -90.6(4) . . . . ?
C4A C5A C6A C7A 1.5(4) . . . . ?
C4A O1A C7A C6A 40.1(3) . . . . ?
C4A O1A C7A C8A -78.3(3) . . . . ?
C5A C6A C7A O1A -26.2(4) . . . . ?
C5A C6A C7A C8A 91.4(4) . . . . ?
C12A O2A C8A C9A -55.6(3) . . . . ?
C12A O2A C8A C14A -174.3(3) . . . . ?
C12A O2A C8A C7A 68.2(3) . . . . ?
O1A C7A C8A O2A -25.9(4) . . . . ?
C6A C7A C8A O2A -138.9(3) . . . . ?
O1A C7A C8A C9A 92.8(3) . . . . ?
C6A C7A C8A C9A -20.2(4) . . . . ?
O1A C7A C8A C14A -140.6(3) . . . . ?
C6A C7A C8A C14A 106.4(3) . . . . ?
O2A C8A C9A C10A 49.5(4) . . . . ?
C14A C8A C9A C10A 165.0(3) . . . . ?
C7A C8A C9A C10A -68.7(4) . . . . ?
C8A C9A C10A O4A -178.9(3) . . . . ?
C8A C9A C10A C11A 2.8(5) . . . . ?
C15A O4A C10A C9A -1.8(6) . . . . ?
C15A O4A C10A C11A 176.6(3) . . . . ?
C9A C10A C11A C1A -175.7(3) . . . . ?
O4A C10A C11A C1A 5.7(4) . . . . ?
C9A C10A C11A C12A -47.3(4) . . . . ?
O4A C10A C11A C12A 134.1(3) . . . . ?
C9A C10A C11A C4A 65.6(4) . . . . ?
O4A C10A C11A C4A -113.0(3) . . . . ?
C2A C1A C11A C10A -160.7(3) . . . . ?
C13A C1A C11A C10A 71.5(4) . . . . ?
C2A C1A C11A C12A 74.4(3) . . . . ?
C13A C1A C11A C12A -53.4(4) . . . . ?
C2A C1A C11A C4A -36.9(3) . . . . ?
C13A C1A C11A C4A -164.6(3) . . . . ?
O1A C4A C11A C10A -96.3(3) . . . . ?
C5A C4A C11A C10A 14.6(4) . . . . ?
C3A C4A C11A C10A 145.2(3) . . . . ?
O1A C4A C11A C1A 136.5(2) . . . . ?
C5A C4A C11A C1A -112.5(3) . . . . ?
C3A C4A C11A C1A 18.0(3) . . . . ?
O1A C4A C11A C12A 18.1(3) . . . . ?
C5A C4A C11A C12A 129.1(3) . . . . ?
C3A C4A C11A C12A -100.4(3) . . . . ?
C8A O2A C12A O3A -173.4(3) . . . . ?
C8A O2A C12A C11A 9.8(4) . . . . ?
C10A C11A C12A O3A -136.2(3) . . . . ?
C1A C11A C12A O3A -5.5(5) . . . . ?
C4A C11A C12A O3A 105.1(4) . . . . ?
C10A C11A C12A O2A 40.4(4) . . . . ?
C1A C11A C12A O2A 171.1(3) . . . . ?
C4A C11A C12A O2A -78.4(3) . . . . ?
C10A O4A C15A O5A -1.9(6) . . . . ?
C10A O4A C15A C16A 178.3(4) . . . . ?
C13B C1B C2B C3B 173.3(3) . . . . ?
C11B C1B C2B C3B 42.6(3) . . . . ?
C1B C2B C3B C4B -29.4(4) . . . . ?
C7B O1B C4B C5B -38.0(3) . . . . ?
C7B O1B C4B C3B -165.2(3) . . . . ?
C7B O1B C4B C11B 80.8(3) . . . . ?
C2B C3B C4B O1B -109.0(3) . . . . ?
C2B C3B C4B C5B 133.2(3) . . . . ?
C2B C3B C4B C11B 5.3(3) . . . . ?
O1B C4B C5B C6B 22.2(4) . . . . ?
C3B C4B C5B C6B 144.9(3) . . . . ?
C11B C4B C5B C6B -91.1(4) . . . . ?
C4B C5B C6B C7B 1.9(4) . . . . ?
C4B O1B C7B C6B 38.9(3) . . . . ?
C4B O1B C7B C8B -78.5(3) . . . . ?
C5B C6B C7B O1B -25.4(4) . . . . ?
C5B C6B C7B C8B 90.8(4) . . . . ?
C12B O2B C8B C9B -54.4(4) . . . . ?
C12B O2B C8B C14B -173.8(3) . . . . ?
C12B O2B C8B C7B 69.6(3) . . . . ?
O1B C7B C8B O2B -26.4(4) . . . . ?
C6B C7B C8B O2B -137.7(3) . . . . ?
O1B C7B C8B C9B 92.1(3) . . . . ?
C6B C7B C8B C9B -19.2(4) . . . . ?
O1B C7B C8B C14B -140.2(3) . . . . ?
C6B C7B C8B C14B 108.5(3) . . . . ?
O2B C8B C9B C10B 49.6(4) . . . . ?
C14B C8B C9B C10B 164.8(3) . . . . ?
C7B C8B C9B C10B -68.7(4) . . . . ?
C8B C9B C10B O4B -176.2(3) . . . . ?
C8B C9B C10B C11B 2.5(5) . . . . ?
C15B O4B C10B C9B 7.1(6) . . . . ?
C15B O4B C10B C11B -171.7(3) . . . . ?
C9B C10B C11B C1B -176.8(3) . . . . ?
O4B C10B C11B C1B 2.2(4) . . . . ?
C9B C10B C11B C12B -47.9(4) . . . . ?
O4B C10B C11B C12B 131.0(3) . . . . ?
C9B C10B C11B C4B 65.8(4) . . . . ?
O4B C10B C11B C4B -115.3(3) . . . . ?
C13B C1B C11B C10B 71.0(4) . . . . ?
C2B C1B C11B C10B -161.1(3) . . . . ?
C13B C1B C11B C12B -53.0(4) . . . . ?
C2B C1B C11B C12B 75.0(3) . . . . ?
C13B C1B C11B C4B -166.0(3) . . . . ?
C2B C1B C11B C4B -38.0(3) . . . . ?
O1B C4B C11B C10B -96.0(3) . . . . ?
C5B C4B C11B C10B 14.8(4) . . . . ?
C3B C4B C11B C10B 145.7(3) . . . . ?
O1B C4B C11B C1B 138.6(3) . . . . ?
C5B C4B C11B C1B -110.5(3) . . . . ?
C3B C4B C11B C1B 20.4(3) . . . . ?
O1B C4B C11B C12B 18.2(3) . . . . ?
C5B C4B C11B C12B 129.0(3) . . . . ?
C3B C4B C11B C12B -100.1(3) . . . . ?
C8B O2B C12B O3B -175.0(3) . . . . ?
C8B O2B C12B C11B 7.4(4) . . . . ?
C10B C11B C12B O3B -134.6(3) . . . . ?
C1B C11B C12B O3B -5.3(5) . . . . ?
C4B C11B C12B O3B 106.2(4) . . . . ?
C10B C11B C12B O2B 42.8(4) . . . . ?
C1B C11B C12B O2B 172.1(3) . . . . ?
C4B C11B C12B O2B -76.3(3) . . . . ?
C10B O4B C15B O5B -10.4(7) . . . . ?
C10B O4B C15B C16B 171.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.072