# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011


data_global
_journal_name_full               'Org.Biomol.Chem.'

_journal_coden_Cambridge         177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Clarke, Paul'
_publ_contact_author_email       pac507@york.ac.uk
loop_
_publ_author_name
P.A.Clarke
M.Iqbal
R.J.G.Black
J.Winn
A.Reeder
A.J.Blake

data_nonlac
_database_code_depnum_ccdc_archive 'CCDC 611039'

_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 O3'
_chemical_formula_sum            'C12 H16 O3'
_chemical_formula_weight         208.25
_chemical_absolute_configuration syn

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   10.396(2)
_cell_length_b                   10.880(2)
_cell_length_c                   19.224(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2174.4(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4020
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      26.4

_exptl_crystal_description       sphenoid
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  .
_exptl_absorpt_correction_T_max  .
_exptl_absorpt_process_details   .

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13687
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_sigmaI/netI    0.045
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2828
_reflns_number_gt                2480
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'enCIFer (Allen et al., 2004); PLATON'

_refine_special_details          
;
Friedel opposites merged.
;

_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^)+(0.050P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   
'sp2 methyl H atoms from delta-F; others placed geometrically'
_refine_ls_hydrogen_treatment    'rigid rotor; riding model'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         2828
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   0.99
_refine_ls_restrained_S_all      0.99
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4176(2) 0.48473(19) 0.89419(11) 0.0274(4) Uani 1 1 d . . .
O1 O 0.41711(15) 0.56375(14) 0.84956(8) 0.0350(4) Uani 1 1 d . . .
C2 C 0.3342(2) 0.3730(2) 0.89251(11) 0.0293(5) Uani 1 1 d . . .
H2 H 0.3915 0.3027 0.8798 0.035 Uiso 1 1 calc R . .
C3 C 0.28128(19) 0.3447(2) 0.96501(11) 0.0291(5) Uani 1 1 d . . .
H3 H 0.2390 0.2623 0.9615 0.035 Uiso 1 1 calc R . .
C4 C 0.1798(2) 0.4314(2) 0.99338(11) 0.0312(5) Uani 1 1 d . . .
H4A H 0.1557 0.4025 1.0404 0.037 Uiso 1 1 calc R . .
H4B H 0.1024 0.4239 0.9637 0.037 Uiso 1 1 calc R . .
C5 C 0.2142(2) 0.5686(2) 0.99867(11) 0.0307(5) Uani 1 1 d . . .
H5A H 0.2582 0.5937 0.9553 0.037 Uiso 1 1 calc R . .
H5B H 0.1336 0.6167 1.0022 0.037 Uiso 1 1 calc R . .
C6 C 0.2994(2) 0.60099(19) 1.05978(11) 0.0302(5) Uani 1 1 d . . .
C7 C 0.4238(2) 0.62695(19) 1.05494(12) 0.0323(5) Uani 1 1 d . . .
H7 H 0.4653 0.6515 1.0967 0.039 Uiso 1 1 calc R . .
C8 C 0.5074(2) 0.6219(2) 0.99035(13) 0.0328(5) Uani 1 1 d . . .
H8A H 0.5965 0.6447 1.0031 0.039 Uiso 1 1 calc R . .
H8B H 0.4757 0.6833 0.9564 0.039 Uiso 1 1 calc R . .
C9 C 0.50902(19) 0.49277(19) 0.95493(12) 0.0282(5) Uani 1 1 d . . .
H9 H 0.5974 0.4823 0.9352 0.034 Uiso 1 1 calc R . .
C10 C 0.4949(2) 0.39567(19) 1.01078(12) 0.0297(5) Uani 1 1 d . . .
O10 O 0.57766(15) 0.37762(15) 1.05349(9) 0.0406(4) Uani 1 1 d . . .
O11 O 0.38670(14) 0.32997(14) 1.01464(8) 0.0337(4) Uani 1 1 d . . .
C11 C 0.2295(2) 0.3778(3) 0.83706(12) 0.0423(6) Uani 1 1 d . . .
H11A H 0.1785 0.3022 0.8388 0.063 Uiso 1 1 calc R . .
H11B H 0.2692 0.3858 0.7911 0.063 Uiso 1 1 calc R . .
H11C H 0.1734 0.4487 0.8457 0.063 Uiso 1 1 calc R . .
C12 C 0.2327(3) 0.6040(2) 1.12900(12) 0.0431(6) Uani 1 1 d . . .
H12A H 0.2954 0.6229 1.1656 0.065 Uiso 1 1 calc R . .
H12B H 0.1935 0.5238 1.1382 0.065 Uiso 1 1 calc R . .
H12C H 0.1658 0.6674 1.1284 0.065 Uiso 1 1 calc R . .
C1' C 0.7482(2) 0.2797(2) 0.68057(11) 0.0300(5) Uani 1 1 d . . .
O1' O 0.83312(16) 0.25492(15) 0.64021(8) 0.0419(4) Uani 1 1 d . . .
C2' C 0.6358(2) 0.3608(2) 0.66304(11) 0.0302(5) Uani 1 1 d . . .
H2' H 0.5612 0.3044 0.6555 0.036 Uiso 1 1 calc R . .
C3' C 0.5993(2) 0.4421(2) 0.72428(11) 0.0287(5) Uani 1 1 d . . .
H3' H 0.5153 0.4808 0.7116 0.034 Uiso 1 1 calc R . .
C4' C 0.6896(2) 0.5476(2) 0.74134(12) 0.0342(5) Uani 1 1 d . . .
H4'A H 0.6542 0.5915 0.7821 0.041 Uiso 1 1 calc R . .
H4'B H 0.6880 0.6057 0.7017 0.041 Uiso 1 1 calc R . .
C5' C 0.8314(2) 0.5168(2) 0.75705(12) 0.0329(5) Uani 1 1 d . . .
H5'A H 0.8616 0.4552 0.7229 0.040 Uiso 1 1 calc R . .
H5'B H 0.8836 0.5920 0.7506 0.040 Uiso 1 1 calc R . .
C6' C 0.8546(2) 0.4677(2) 0.82933(12) 0.0314(5) Uani 1 1 d . . .
C7' C 0.8732(2) 0.3502(2) 0.84391(12) 0.0330(5) Uani 1 1 d . . .
H7' H 0.8873 0.3304 0.8914 0.040 Uiso 1 1 calc R . .
C8' C 0.8744(2) 0.2441(2) 0.79340(13) 0.0345(5) Uani 1 1 d . . .
H8'A H 0.8954 0.1682 0.8193 0.041 Uiso 1 1 calc R . .
H8'B H 0.9442 0.2581 0.7592 0.041 Uiso 1 1 calc R . .
C9' C 0.74643(19) 0.2229(2) 0.75286(11) 0.0279(5) Uani 1 1 d . . .
H9' H 0.7392 0.1321 0.7458 0.033 Uiso 1 1 calc R . .
C10' C 0.63374(19) 0.25930(19) 0.79753(11) 0.0259(4) Uani 1 1 d . . .
O10' O 0.59661(15) 0.19738(14) 0.84546(8) 0.0357(4) Uani 1 1 d . . .
O11' O 0.57345(13) 0.36646(13) 0.78583(8) 0.0290(3) Uani 1 1 d . . .
C11' C 0.6523(3) 0.4323(3) 0.59526(12) 0.0451(6) Uani 1 1 d . . .
H11D H 0.6761 0.3755 0.5578 0.068 Uiso 1 1 calc R . .
H11E H 0.7201 0.4940 0.6010 0.068 Uiso 1 1 calc R . .
H11F H 0.5713 0.4732 0.5834 0.068 Uiso 1 1 calc R . .
C12' C 0.8572(3) 0.5643(2) 0.88578(13) 0.0445(6) Uani 1 1 d . . .
H12D H 0.8599 0.5242 0.9314 0.067 Uiso 1 1 calc R . .
H12E H 0.7798 0.6154 0.8825 0.067 Uiso 1 1 calc R . .
H12F H 0.9337 0.6160 0.8801 0.067 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
C1 0.0262(10) 0.0268(11) 0.0292(11) -0.0001(9) 0.0098(9) 0.0070(9)
O1 0.0413(9) 0.0307(8) 0.0331(8) 0.0048(7) 0.0113(7) 0.0081(8)
C2 0.0293(10) 0.0288(11) 0.0300(11) -0.0038(9) 0.0036(9) 0.0023(10)
C3 0.0279(10) 0.0267(11) 0.0327(12) 0.0000(9) 0.0010(9) -0.0053(9)
C4 0.0256(10) 0.0379(12) 0.0301(11) -0.0011(10) 0.0041(9) -0.0055(10)
C5 0.0263(10) 0.0327(12) 0.0330(12) 0.0007(9) 0.0059(9) 0.0052(9)
C6 0.0373(12) 0.0225(10) 0.0308(11) -0.0023(9) 0.0028(10) 0.0020(9)
C7 0.0399(12) 0.0229(10) 0.0341(12) -0.0023(9) -0.0029(10) -0.0002(10)
C8 0.0269(10) 0.0259(11) 0.0455(13) -0.0006(10) -0.0019(10) -0.0046(9)
C9 0.0221(9) 0.0234(10) 0.0390(12) 0.0028(9) 0.0057(10) 0.0007(8)
C10 0.0277(10) 0.0245(11) 0.0370(12) -0.0011(9) 0.0019(10) 0.0053(9)
O10 0.0356(8) 0.0367(9) 0.0494(10) 0.0034(8) -0.0104(8) 0.0074(8)
O11 0.0344(8) 0.0293(8) 0.0375(9) 0.0080(7) -0.0009(7) -0.0028(7)
C11 0.0437(13) 0.0505(15) 0.0326(13) -0.0074(11) -0.0030(11) -0.0018(12)
C12 0.0537(15) 0.0416(14) 0.0340(13) -0.0046(10) 0.0074(11) -0.0040(12)
C1' 0.0292(10) 0.0283(11) 0.0323(12) -0.0078(9) 0.0056(10) -0.0081(9)
O1' 0.0406(9) 0.0446(10) 0.0404(9) -0.0103(8) 0.0164(8) -0.0054(8)
C2' 0.0296(10) 0.0337(11) 0.0273(11) -0.0006(9) 0.0016(9) -0.0080(10)
C3' 0.0284(10) 0.0279(11) 0.0299(11) 0.0069(9) 0.0015(9) 0.0018(9)
C4' 0.0394(12) 0.0259(11) 0.0372(13) 0.0059(10) -0.0012(10) 0.0015(10)
C5' 0.0341(11) 0.0250(11) 0.0396(13) 0.0018(9) 0.0019(10) -0.0085(10)
C6' 0.0276(10) 0.0313(12) 0.0352(12) -0.0034(9) -0.0025(10) -0.0058(9)
C7' 0.0287(11) 0.0346(12) 0.0357(13) -0.0007(10) -0.0066(10) -0.0008(9)
C8' 0.0292(11) 0.0292(12) 0.0452(13) 0.0008(10) -0.0011(10) 0.0046(10)
C9' 0.0288(10) 0.0213(10) 0.0336(12) -0.0042(8) 0.0027(10) -0.0006(9)
C10' 0.0258(10) 0.0239(10) 0.0281(11) -0.0017(9) -0.0011(9) -0.0011(9)
O10' 0.0374(9) 0.0349(8) 0.0348(9) 0.0097(7) 0.0068(7) 0.0012(7)
O11' 0.0301(7) 0.0255(8) 0.0314(8) 0.0031(6) 0.0085(6) 0.0041(7)
C11' 0.0489(15) 0.0549(15) 0.0315(12) 0.0085(12) -0.0017(11) -0.0103(14)
C12' 0.0493(15) 0.0380(13) 0.0461(14) -0.0094(12) -0.0080(12) -0.0062(13)

_geom_special_details            
;
?
;

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
C1 O1 1.215(2) . ?
C1 C2 1.494(3) . ?
C1 C9 1.508(3) . ?
C2 C11 1.524(3) . ?
C2 C3 1.530(3) . ?
C2 H2 1.0000 . ?
C3 O11 1.462(2) . ?
C3 C4 1.517(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.539(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.513(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.327(3) . ?
C6 C12 1.501(3) . ?
C7 C8 1.516(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.561(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.513(3) . ?
C9 H9 1.0000 . ?
C10 O10 1.206(3) . ?
C10 O11 1.335(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C1' O1' 1.206(3) . ?
C1' C2' 1.502(3) . ?
C1' C9' 1.521(3) . ?
C2' C3' 1.521(3) . ?
C2' C11' 1.527(3) . ?
C2' H2' 1.0000 . ?
C3' O11' 1.466(2) . ?
C3' C4' 1.519(3) . ?
C3' H3' 1.0000 . ?
C4' C5' 1.541(3) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C5' C6' 1.508(3) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C6' C7' 1.323(3) . ?
C6' C12' 1.511(3) . ?
C7' C8' 1.508(3) . ?
C7' H7' 0.9500 . ?
C8' C9' 1.559(3) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C9' C10' 1.506(3) . ?
C9' H9' 1.0000 . ?
C10' O10' 1.205(2) . ?
C10' O11' 1.343(2) . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 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
O1 C1 C2 123.9(2) . . ?
O1 C1 C9 120.6(2) . . ?
C2 C1 C9 115.46(18) . . ?
C1 C2 C11 113.7(2) . . ?
C1 C2 C3 110.67(18) . . ?
C11 C2 C3 112.80(18) . . ?
C1 C2 H2 106.4 . . ?
C11 C2 H2 106.4 . . ?
C3 C2 H2 106.4 . . ?
O11 C3 C4 110.78(17) . . ?
O11 C3 C2 110.32(16) . . ?
C4 C3 C2 116.89(18) . . ?
O11 C3 H3 106.0 . . ?
C4 C3 H3 106.0 . . ?
C2 C3 H3 106.0 . . ?
C3 C4 C5 117.74(17) . . ?
C3 C4 H4A 107.9 . . ?
C5 C4 H4A 107.9 . . ?
C3 C4 H4B 107.9 . . ?
C5 C4 H4B 107.9 . . ?
H4A C4 H4B 107.2 . . ?
C6 C5 C4 114.43(18) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C12 120.5(2) . . ?
C7 C6 C5 124.4(2) . . ?
C12 C6 C5 115.05(19) . . ?
C6 C7 C8 127.4(2) . . ?
C6 C7 H7 116.3 . . ?
C8 C7 H7 116.3 . . ?
C7 C8 C9 113.36(17) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C1 C9 C10 116.59(17) . . ?
C1 C9 C8 112.52(17) . . ?
C10 C9 C8 108.52(17) . . ?
C1 C9 H9 106.2 . . ?
C10 C9 H9 106.2 . . ?
C8 C9 H9 106.2 . . ?
O10 C10 O11 118.4(2) . . ?
O10 C10 C9 121.83(19) . . ?
O11 C10 C9 119.69(18) . . ?
C10 O11 C3 122.47(16) . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1' C1' C2' 123.8(2) . . ?
O1' C1' C9' 120.4(2) . . ?
C2' C1' C9' 115.75(17) . . ?
C1' C2' C3' 111.24(17) . . ?
C1' C2' C11' 113.79(19) . . ?
C3' C2' C11' 113.10(19) . . ?
C1' C2' H2' 106.0 . . ?
C3' C2' H2' 106.0 . . ?
C11' C2' H2' 106.0 . . ?
O11' C3' C4' 111.29(17) . . ?
O11' C3' C2' 110.13(17) . . ?
C4' C3' C2' 116.87(18) . . ?
O11' C3' H3' 105.9 . . ?
C4' C3' H3' 105.9 . . ?
C2' C3' H3' 105.9 . . ?
C3' C4' C5' 118.00(19) . . ?
C3' C4' H4'A 107.8 . . ?
C5' C4' H4'A 107.8 . . ?
C3' C4' H4'B 107.8 . . ?
C5' C4' H4'B 107.8 . . ?
H4'A C4' H4'B 107.1 . . ?
C6' C5' C4' 114.27(19) . . ?
C6' C5' H5'A 108.7 . . ?
C4' C5' H5'A 108.7 . . ?
C6' C5' H5'B 108.7 . . ?
C4' C5' H5'B 108.7 . . ?
H5'A C5' H5'B 107.6 . . ?
C7' C6' C5' 124.1(2) . . ?
C7' C6' C12' 121.2(2) . . ?
C5' C6' C12' 114.68(19) . . ?
C6' C7' C8' 127.2(2) . . ?
C6' C7' H7' 116.4 . . ?
C8' C7' H7' 116.4 . . ?
C7' C8' C9' 115.36(18) . . ?
C7' C8' H8'A 108.4 . . ?
C9' C8' H8'A 108.4 . . ?
C7' C8' H8'B 108.4 . . ?
C9' C8' H8'B 108.4 . . ?
H8'A C8' H8'B 107.5 . . ?
C10' C9' C1' 115.05(18) . . ?
C10' C9' C8' 109.86(16) . . ?
C1' C9' C8' 112.71(18) . . ?
C10' C9' H9' 106.2 . . ?
C1' C9' H9' 106.2 . . ?
C8' C9' H9' 106.2 . . ?
O10' C10' O11' 117.65(18) . . ?
O10' C10' C9' 122.56(19) . . ?
O11' C10' C9' 119.75(18) . . ?
C10' O11' C3' 122.48(16) . . ?
C2' C11' H11D 109.5 . . ?
C2' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C2' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C6' C12' H12D 109.5 . . ?
C6' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C6' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 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
O1 C1 C2 C11 -11.1(3) . . . . ?
C9 C1 C2 C11 171.02(18) . . . . ?
O1 C1 C2 C3 -139.2(2) . . . . ?
C9 C1 C2 C3 42.9(2) . . . . ?
C1 C2 C3 O11 -56.6(2) . . . . ?
C11 C2 C3 O11 174.80(18) . . . . ?
C1 C2 C3 C4 71.1(2) . . . . ?
C11 C2 C3 C4 -57.5(3) . . . . ?
O11 C3 C4 C5 70.5(2) . . . . ?
C2 C3 C4 C5 -57.0(3) . . . . ?
C3 C4 C5 C6 -77.4(3) . . . . ?
C4 C5 C6 C7 105.0(2) . . . . ?
C4 C5 C6 C12 -75.8(2) . . . . ?
C12 C6 C7 C8 176.5(2) . . . . ?
C5 C6 C7 C8 -4.3(4) . . . . ?
C6 C7 C8 C9 -57.6(3) . . . . ?
O1 C1 C9 C10 175.12(18) . . . . ?
C2 C1 C9 C10 -6.9(3) . . . . ?
O1 C1 C9 C8 48.8(2) . . . . ?
C2 C1 C9 C8 -133.17(18) . . . . ?
C7 C8 C9 C1 98.4(2) . . . . ?
C7 C8 C9 C10 -32.2(2) . . . . ?
C1 C9 C10 O10 164.4(2) . . . . ?
C8 C9 C10 O10 -67.4(3) . . . . ?
C1 C9 C10 O11 -17.6(3) . . . . ?
C8 C9 C10 O11 110.7(2) . . . . ?
O10 C10 O11 C3 -179.57(19) . . . . ?
C9 C10 O11 C3 2.3(3) . . . . ?
C4 C3 O11 C10 -96.0(2) . . . . ?
C2 C3 O11 C10 35.0(3) . . . . ?
O1' C1' C2' C3' -141.9(2) . . . . ?
C9' C1' C2' C3' 41.2(2) . . . . ?
O1' C1' C2' C11' -12.7(3) . . . . ?
C9' C1' C2' C11' 170.40(19) . . . . ?
C1' C2' C3' O11' -55.7(2) . . . . ?
C11' C2' C3' O11' 174.77(17) . . . . ?
C1' C2' C3' C4' 72.5(2) . . . . ?
C11' C2' C3' C4' -57.0(3) . . . . ?
O11' C3' C4' C5' 70.4(2) . . . . ?
C2' C3' C4' C5' -57.3(3) . . . . ?
C3' C4' C5' C6' -78.3(3) . . . . ?
C4' C5' C6' C7' 102.3(3) . . . . ?
C4' C5' C6' C12' -78.5(3) . . . . ?
C5' C6' C7' C8' -0.3(4) . . . . ?
C12' C6' C7' C8' -179.5(2) . . . . ?
C6' C7' C8' C9' -61.3(3) . . . . ?
O1' C1' C9' C10' -178.75(19) . . . . ?
C2' C1' C9' C10' -1.8(3) . . . . ?
O1' C1' C9' C8' 54.2(3) . . . . ?
C2' C1' C9' C8' -128.8(2) . . . . ?
C7' C8' C9' C10' -32.0(3) . . . . ?
C7' C8' C9' C1' 97.7(2) . . . . ?
C1' C9' C10' O10' 156.8(2) . . . . ?
C8' C9' C10' O10' -74.7(3) . . . . ?
C1' C9' C10' O11' -25.4(3) . . . . ?
C8' C9' C10' O11' 103.1(2) . . . . ?
O10' C10' O11' C3' -172.29(19) . . . . ?
C9' C10' O11' C3' 9.8(3) . . . . ?
C4' C3' O11' C10' -100.0(2) . . . . ?
C2' C3' O11' C10' 31.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996

_refine_diff_density_max         0.22
_refine_diff_density_min         -0.14
_refine_diff_density_rms         0.04

#===END of CIF

# Attachment 'OLCMEN.CIF'

data_olcmen
_database_code_depnum_ccdc_archive 'CCDC 611040'

_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 O3'
_chemical_formula_sum            'C12 H16 O3'
_chemical_formula_weight         208.25
_chemical_absolute_configuration unk

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2'

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

_cell_length_a                   24.170(4)
_cell_length_b                   7.6936(12)
_cell_length_c                   12.380(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.922(3)
_cell_angle_gamma                90.00
_cell_volume                     2120.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1996
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      27.4

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  .
_exptl_absorpt_correction_T_max  .
_exptl_absorpt_process_details   .

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5895
_diffrn_reflns_av_R_equivalents  0.084
_diffrn_reflns_av_sigmaI/netI    0.079
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2566
_reflns_number_gt                1989
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'enCIFer (Allen et al., 2004); PLATON'

_refine_special_details          
;
?
;

_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^)+(0.063P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2566
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.121
_refine_ls_wR_factor_gt          0.114
_refine_ls_goodness_of_fit_ref   0.96
_refine_ls_restrained_S_all      0.96
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.94318(13) 0.3186(5) 0.1018(2) 0.0221(7) Uani 1 1 d . . .
O1 O 0.99738(10) 0.3182(4) 0.13970(19) 0.0330(6) Uani 1 1 d . . .
C2 C 0.90479(13) 0.1599(4) 0.0849(3) 0.0216(6) Uani 1 1 d . . .
C3 C 0.86059(14) 0.1840(4) 0.1473(3) 0.0239(7) Uani 1 1 d . . .
H3 H 0.8799 0.1391 0.2293 0.029 Uiso 1 1 calc R . .
O3 O 0.83993(11) 0.3623(3) 0.1506(2) 0.0264(5) Uani 1 1 d . . .
C4 C 0.80577(14) 0.0711(5) 0.0792(3) 0.0263(7) Uani 1 1 d . . .
H4A H 0.7683 0.1385 0.0606 0.032 Uiso 1 1 calc R . .
H4B H 0.8044 -0.0316 0.1263 0.032 Uiso 1 1 calc R . .
C5 C 0.81240(14) 0.0143(5) -0.0339(3) 0.0276(8) Uani 1 1 d . . .
H5A H 0.8254 -0.1086 -0.0282 0.033 Uiso 1 1 calc R . .
H5B H 0.7737 0.0266 -0.1020 0.033 Uiso 1 1 calc R . .
C6 C 0.86006(13) 0.1338(5) -0.0473(3) 0.0224(7) Uani 1 1 d . . .
C7 C 0.83042(14) 0.3096(5) -0.1016(3) 0.0272(7) Uani 1 1 d . . .
H7A H 0.8114 0.2962 -0.1879 0.033 Uiso 1 1 calc R . .
H7B H 0.7981 0.3356 -0.0737 0.033 Uiso 1 1 calc R . .
C8 C 0.87304(15) 0.4638(5) -0.0733(3) 0.0283(7) Uani 1 1 d . . .
H8A H 0.8501 0.5714 -0.1057 0.034 Uiso 1 1 calc R . .
H8B H 0.9024 0.4472 -0.1101 0.034 Uiso 1 1 calc R . .
C9 C 0.90678(14) 0.4823(5) 0.0614(3) 0.0229(7) Uani 1 1 d . . .
H9 H 0.9340 0.5856 0.0797 0.027 Uiso 1 1 calc R . .
C10 C 0.86100(13) 0.5039(4) 0.1164(2) 0.0218(7) Uani 1 1 d . . .
O10 O 0.84179(11) 0.6437(3) 0.1264(2) 0.0309(6) Uani 1 1 d . . .
C11 C 0.94297(15) -0.0006(5) 0.1367(3) 0.0338(8) Uani 1 1 d . . .
H11A H 0.9696 0.0226 0.2184 0.051 Uiso 1 1 calc R . .
H11B H 0.9671 -0.0284 0.0912 0.051 Uiso 1 1 calc R . .
H11C H 0.9167 -0.0990 0.1339 0.051 Uiso 1 1 calc R . .
C12 C 0.88995(17) 0.0529(5) -0.1242(3) 0.0357(9) Uani 1 1 d . . .
H12A H 0.9086 -0.0579 -0.0901 0.054 Uiso 1 1 calc R . .
H12B H 0.9208 0.1321 -0.1285 0.054 Uiso 1 1 calc R . .
H12C H 0.8596 0.0328 -0.2033 0.054 Uiso 1 1 calc R . .
C1' C 0.90865(13) 0.4888(5) 0.4182(2) 0.0230(7) Uani 1 1 d . . .
O1' O 0.94674(9) 0.4929(4) 0.37722(19) 0.0320(6) Uani 1 1 d . . .
C2' C 0.87778(13) 0.6453(4) 0.4412(3) 0.0210(6) Uani 1 1 d . . .
C3' C 0.80948(14) 0.6278(5) 0.3690(3) 0.0237(7) Uani 1 1 d . . .
H3' H 0.7996 0.6786 0.2893 0.028 Uiso 1 1 calc R . .
O3' O 0.78516(10) 0.4501(3) 0.35661(19) 0.0273(5) Uani 1 1 d . . .
C4' C 0.77914(14) 0.7375(5) 0.4348(3) 0.0286(8) Uani 1 1 d . . .
H4'A H 0.7455 0.6722 0.4424 0.034 Uiso 1 1 calc R . .
H4'B H 0.7632 0.8469 0.3919 0.034 Uiso 1 1 calc R . .
C5' C 0.82809(14) 0.7768(5) 0.5572(3) 0.0302(8) Uani 1 1 d . . .
H5'A H 0.8408 0.8999 0.5625 0.036 Uiso 1 1 calc R . .
H5'B H 0.8128 0.7534 0.6193 0.036 Uiso 1 1 calc R . .
C6' C 0.88113(14) 0.6548(5) 0.5705(3) 0.0253(7) Uani 1 1 d . . .
C7' C 0.86902(16) 0.4758(5) 0.6128(3) 0.0325(8) Uani 1 1 d . . .
H7'A H 0.8815 0.4796 0.6990 0.039 Uiso 1 1 calc R . .
H7'B H 0.8253 0.4529 0.5777 0.039 Uiso 1 1 calc R . .
C8' C 0.90147(17) 0.3259(5) 0.5820(3) 0.0327(8) Uani 1 1 d . . .
H8'A H 0.8895 0.2146 0.6067 0.039 Uiso 1 1 calc R . .
H8'B H 0.9454 0.3398 0.6244 0.039 Uiso 1 1 calc R . .
C9' C 0.88564(14) 0.3225(5) 0.4477(3) 0.0260(7) Uani 1 1 d . . .
H9' H 0.9062 0.2218 0.4280 0.031 Uiso 1 1 calc R . .
C10' C 0.81843(15) 0.3052(5) 0.3826(3) 0.0253(7) Uani 1 1 d . . .
O10' O 0.79362(12) 0.1673(4) 0.3583(2) 0.0395(6) Uani 1 1 d . . .
C11' C 0.89900(15) 0.8116(5) 0.4016(3) 0.0314(8) Uani 1 1 d . . .
H11D H 0.9422 0.8270 0.4468 0.047 Uiso 1 1 calc R . .
H11E H 0.8772 0.9114 0.4147 0.047 Uiso 1 1 calc R . .
H11F H 0.8913 0.8031 0.3180 0.047 Uiso 1 1 calc R . .
C12' C 0.94102(15) 0.7275(5) 0.6581(3) 0.0346(9) Uani 1 1 d . . .
H12D H 0.9487 0.8411 0.6307 0.052 Uiso 1 1 calc R . .
H12E H 0.9736 0.6474 0.6642 0.052 Uiso 1 1 calc R . .
H12F H 0.9390 0.7405 0.7352 0.052 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
C1 0.0178(15) 0.0328(19) 0.0158(13) -0.0032(14) 0.0066(11) -0.0010(15)
O1 0.0200(11) 0.0416(16) 0.0356(13) -0.0086(13) 0.0091(9) -0.0041(12)
C2 0.0192(14) 0.0226(17) 0.0227(15) 0.0014(13) 0.0077(12) 0.0045(14)
C3 0.0242(16) 0.0247(19) 0.0229(16) 0.0046(13) 0.0095(13) 0.0022(14)
O3 0.0310(13) 0.0238(13) 0.0296(12) -0.0019(10) 0.0175(10) 0.0004(10)
C4 0.0222(16) 0.0280(18) 0.0314(18) 0.0041(14) 0.0132(14) -0.0016(14)
C5 0.0242(16) 0.031(2) 0.0266(16) -0.0021(15) 0.0092(13) -0.0043(15)
C6 0.0190(15) 0.0268(17) 0.0209(15) -0.0027(14) 0.0074(12) -0.0010(14)
C7 0.0296(17) 0.0329(19) 0.0170(14) 0.0012(15) 0.0067(12) 0.0000(16)
C8 0.0403(19) 0.0269(19) 0.0208(15) 0.0057(14) 0.0154(14) 0.0019(16)
C9 0.0262(16) 0.0208(17) 0.0237(15) -0.0027(14) 0.0118(12) -0.0057(14)
C10 0.0231(16) 0.0234(17) 0.0169(14) -0.0021(14) 0.0056(12) 0.0019(14)
O10 0.0361(13) 0.0291(14) 0.0296(13) -0.0029(11) 0.0151(10) 0.0014(12)
C11 0.0259(17) 0.030(2) 0.043(2) 0.0056(18) 0.0110(15) 0.0050(16)
C12 0.039(2) 0.039(2) 0.0342(19) -0.0129(16) 0.0199(16) -0.0055(18)
C1' 0.0181(15) 0.0338(19) 0.0149(13) -0.0006(15) 0.0039(11) 0.0014(15)
O1' 0.0227(12) 0.0426(16) 0.0357(13) -0.0028(13) 0.0168(10) 0.0016(13)
C2' 0.0200(15) 0.0224(17) 0.0216(15) -0.0018(14) 0.0090(12) -0.0012(14)
C3' 0.0197(15) 0.0258(18) 0.0256(16) -0.0002(14) 0.0089(13) 0.0007(14)
O3' 0.0213(12) 0.0288(14) 0.0309(12) -0.0048(10) 0.0092(10) -0.0034(10)
C4' 0.0194(16) 0.035(2) 0.0303(17) -0.0031(15) 0.0087(13) 0.0013(15)
C5' 0.0255(16) 0.036(2) 0.0301(17) -0.0115(15) 0.0114(13) -0.0001(15)
C6' 0.0241(16) 0.0287(18) 0.0244(16) -0.0070(15) 0.0107(13) -0.0004(15)
C7' 0.0408(19) 0.041(2) 0.0182(15) 0.0016(16) 0.0144(14) -0.0036(19)
C8' 0.0402(19) 0.032(2) 0.0219(16) 0.0056(16) 0.0075(14) 0.0028(18)
C9' 0.0301(17) 0.0257(18) 0.0210(16) -0.0004(14) 0.0086(13) 0.0079(16)
C10' 0.0372(18) 0.0205(17) 0.0242(15) -0.0022(14) 0.0186(14) -0.0023(16)
O10' 0.0438(15) 0.0279(15) 0.0509(16) -0.0077(12) 0.0228(13) -0.0091(13)
C11' 0.0308(17) 0.0263(18) 0.0409(19) 0.0005(17) 0.0181(15) -0.0041(16)
C12' 0.0314(19) 0.043(2) 0.0256(18) -0.0142(16) 0.0064(14) -0.0043(17)

_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
C1 O1 1.207(4) . ?
C1 C2 1.498(5) . ?
C1 C9 1.506(5) . ?
C2 C11 1.525(5) . ?
C2 C3 1.554(4) . ?
C2 C6 1.584(4) . ?
C3 O3 1.466(4) . ?
C3 C4 1.533(5) . ?
C3 H3 1.0000 . ?
O3 C10 1.339(4) . ?
C4 C5 1.534(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.533(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C12 1.534(4) . ?
C6 C7 1.555(5) . ?
C7 C8 1.520(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.551(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(4) . ?
C9 H9 1.0000 . ?
C10 O10 1.197(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C1' O1' 1.212(3) . ?
C1' C9' 1.496(5) . ?
C1' C2' 1.501(5) . ?
C2' C11' 1.528(5) . ?
C2' C3' 1.547(4) . ?
C2' C6' 1.572(4) . ?
C3' O3' 1.473(4) . ?
C3' C4' 1.542(4) . ?
C3' H3' 1.0000 . ?
O3' C10' 1.339(4) . ?
C4' C5' 1.546(4) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C5' C6' 1.545(5) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C6' C12' 1.537(5) . ?
C6' C7' 1.542(5) . ?
C7' C8' 1.524(5) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C8' C9' 1.554(4) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C9' C10' 1.512(5) . ?
C9' H9' 1.0000 . ?
C10' O10' 1.198(4) . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 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
O1 C1 C2 124.9(3) . . ?
O1 C1 C9 122.4(3) . . ?
C2 C1 C9 112.7(2) . . ?
C1 C2 C11 111.1(2) . . ?
C1 C2 C3 110.0(3) . . ?
C11 C2 C3 107.9(3) . . ?
C1 C2 C6 112.6(2) . . ?
C11 C2 C6 112.9(3) . . ?
C3 C2 C6 101.8(2) . . ?
O3 C3 C4 108.3(3) . . ?
O3 C3 C2 115.7(3) . . ?
C4 C3 C2 105.9(3) . . ?
O3 C3 H3 108.9 . . ?
C4 C3 H3 108.9 . . ?
C2 C3 H3 108.9 . . ?
C10 O3 C3 125.2(2) . . ?
C3 C4 C5 106.7(2) . . ?
C3 C4 H4A 110.4 . . ?
C5 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
C5 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C6 C5 C4 106.1(3) . . ?
C6 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C5 C6 C12 112.3(3) . . ?
C5 C6 C7 109.2(3) . . ?
C12 C6 C7 109.5(3) . . ?
C5 C6 C2 101.7(2) . . ?
C12 C6 C2 113.3(3) . . ?
C7 C6 C2 110.5(3) . . ?
C8 C7 C6 115.0(3) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 110.2(2) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C1 C9 C10 112.1(3) . . ?
C1 C9 C8 106.0(3) . . ?
C10 C9 C8 108.8(2) . . ?
C1 C9 H9 109.9 . . ?
C10 C9 H9 110.0 . . ?
C8 C9 H9 110.0 . . ?
O10 C10 O3 119.2(3) . . ?
O10 C10 C9 121.7(3) . . ?
O3 C10 C9 119.1(3) . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1' C1' C9' 122.7(3) . . ?
O1' C1' C2' 125.0(3) . . ?
C9' C1' C2' 112.4(2) . . ?
C1' C2' C11' 110.9(2) . . ?
C1' C2' C3' 108.5(3) . . ?
C11' C2' C3' 107.7(3) . . ?
C1' C2' C6' 113.5(3) . . ?
C11' C2' C6' 113.4(3) . . ?
C3' C2' C6' 102.2(2) . . ?
O3' C3' C4' 108.1(2) . . ?
O3' C3' C2' 115.7(3) . . ?
C4' C3' C2' 105.5(3) . . ?
O3' C3' H3' 109.1 . . ?
C4' C3' H3' 109.1 . . ?
C2' C3' H3' 109.1 . . ?
C10' O3' C3' 124.8(2) . . ?
C3' C4' C5' 106.5(3) . . ?
C3' C4' H4'A 110.4 . . ?
C5' C4' H4'A 110.4 . . ?
C3' C4' H4'B 110.4 . . ?
C5' C4' H4'B 110.4 . . ?
H4'A C4' H4'B 108.6 . . ?
C6' C5' C4' 105.8(3) . . ?
C6' C5' H5'A 110.6 . . ?
C4' C5' H5'A 110.6 . . ?
C6' C5' H5'B 110.6 . . ?
C4' C5' H5'B 110.6 . . ?
H5'A C5' H5'B 108.7 . . ?
C12' C6' C7' 109.7(3) . . ?
C12' C6' C5' 111.6(3) . . ?
C7' C6' C5' 108.6(3) . . ?
C12' C6' C2' 113.3(3) . . ?
C7' C6' C2' 111.3(3) . . ?
C5' C6' C2' 102.0(2) . . ?
C8' C7' C6' 114.0(3) . . ?
C8' C7' H7'A 108.8 . . ?
C6' C7' H7'A 108.8 . . ?
C8' C7' H7'B 108.8 . . ?
C6' C7' H7'B 108.8 . . ?
H7'A C7' H7'B 107.7 . . ?
C7' C8' C9' 110.2(3) . . ?
C7' C8' H8'A 109.6 . . ?
C9' C8' H8'A 109.6 . . ?
C7' C8' H8'B 109.6 . . ?
C9' C8' H8'B 109.6 . . ?
H8'A C8' H8'B 108.1 . . ?
C1' C9' C10' 111.7(3) . . ?
C1' C9' C8' 106.6(3) . . ?
C10' C9' C8' 109.7(3) . . ?
C1' C9' H9' 109.6 . . ?
C10' C9' H9' 109.6 . . ?
C8' C9' H9' 109.6 . . ?
O10' C10' O3' 118.8(3) . . ?
O10' C10' C9' 122.7(3) . . ?
O3' C10' C9' 118.4(3) . . ?
C2' C11' H11D 109.5 . . ?
C2' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C2' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C6' C12' H12D 109.5 . . ?
C6' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C6' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 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
O1 C1 C2 C11 7.4(4) . . . . ?
C9 C1 C2 C11 -174.9(2) . . . . ?
O1 C1 C2 C3 126.9(3) . . . . ?
C9 C1 C2 C3 -55.4(3) . . . . ?
O1 C1 C2 C6 -120.3(3) . . . . ?
C9 C1 C2 C6 57.3(3) . . . . ?
C1 C2 C3 O3 32.4(4) . . . . ?
C11 C2 C3 O3 153.8(3) . . . . ?
C6 C2 C3 O3 -87.2(3) . . . . ?
C1 C2 C3 C4 152.3(3) . . . . ?
C11 C2 C3 C4 -86.3(3) . . . . ?
C6 C2 C3 C4 32.8(3) . . . . ?
C4 C3 O3 C10 -126.3(3) . . . . ?
C2 C3 O3 C10 -7.7(4) . . . . ?
O3 C3 C4 C5 113.3(3) . . . . ?
C2 C3 C4 C5 -11.3(3) . . . . ?
C3 C4 C5 C6 -15.7(3) . . . . ?
C4 C5 C6 C12 157.2(3) . . . . ?
C4 C5 C6 C7 -81.2(3) . . . . ?
C4 C5 C6 C2 35.7(3) . . . . ?
C1 C2 C6 C5 -159.5(3) . . . . ?
C11 C2 C6 C5 73.7(3) . . . . ?
C3 C2 C6 C5 -41.8(3) . . . . ?
C1 C2 C6 C12 79.8(3) . . . . ?
C11 C2 C6 C12 -47.1(4) . . . . ?
C3 C2 C6 C12 -162.5(3) . . . . ?
C1 C2 C6 C7 -43.6(3) . . . . ?
C11 C2 C6 C7 -170.4(3) . . . . ?
C3 C2 C6 C7 74.2(3) . . . . ?
C5 C6 C7 C8 154.8(3) . . . . ?
C12 C6 C7 C8 -81.8(3) . . . . ?
C2 C6 C7 C8 43.7(3) . . . . ?
C6 C7 C8 C9 -54.7(4) . . . . ?
O1 C1 C9 C10 -129.2(3) . . . . ?
C2 C1 C9 C10 53.1(3) . . . . ?
O1 C1 C9 C8 112.2(3) . . . . ?
C2 C1 C9 C8 -65.5(3) . . . . ?
C7 C8 C9 C1 62.6(3) . . . . ?
C7 C8 C9 C10 -58.1(4) . . . . ?
C3 O3 C10 O10 -177.8(3) . . . . ?
C3 O3 C10 C9 4.7(4) . . . . ?
C1 C9 C10 O10 155.9(3) . . . . ?
C8 C9 C10 O10 -87.2(4) . . . . ?
C1 C9 C10 O3 -26.7(4) . . . . ?
C8 C9 C10 O3 90.2(3) . . . . ?
O1' C1' C2' C11' 2.2(4) . . . . ?
C9' C1' C2' C11' -175.8(3) . . . . ?
O1' C1' C2' C3' 120.3(3) . . . . ?
C9' C1' C2' C3' -57.7(3) . . . . ?
O1' C1' C2' C6' -126.8(3) . . . . ?
C9' C1' C2' C6' 55.3(3) . . . . ?
C1' C2' C3' O3' 35.5(3) . . . . ?
C11' C2' C3' O3' 155.7(3) . . . . ?
C6' C2' C3' O3' -84.6(3) . . . . ?
C1' C2' C3' C4' 155.0(3) . . . . ?
C11' C2' C3' C4' -84.9(3) . . . . ?
C6' C2' C3' C4' 34.8(3) . . . . ?
C4' C3' O3' C10' -131.4(3) . . . . ?
C2' C3' O3' C10' -13.4(4) . . . . ?
O3' C3' C4' C5' 110.4(3) . . . . ?
C2' C3' C4' C5' -14.0(4) . . . . ?
C3' C4' C5' C6' -12.9(4) . . . . ?
C4' C5' C6' C12' 155.4(3) . . . . ?
C4' C5' C6' C7' -83.5(3) . . . . ?
C4' C5' C6' C2' 34.1(3) . . . . ?
C1' C2' C6' C12' 80.9(4) . . . . ?
C11' C2' C6' C12' -46.8(4) . . . . ?
C3' C2' C6' C12' -162.4(3) . . . . ?
C1' C2' C6' C7' -43.3(3) . . . . ?
C11' C2' C6' C7' -171.0(3) . . . . ?
C3' C2' C6' C7' 73.4(3) . . . . ?
C1' C2' C6' C5' -158.9(3) . . . . ?
C11' C2' C6' C5' 73.4(3) . . . . ?
C3' C2' C6' C5' -42.2(3) . . . . ?
C12' C6' C7' C8' -82.0(3) . . . . ?
C5' C6' C7' C8' 155.8(3) . . . . ?
C2' C6' C7' C8' 44.2(4) . . . . ?
C6' C7' C8' C9' -55.3(4) . . . . ?
O1' C1' C9' C10' -121.9(3) . . . . ?
C2' C1' C9' C10' 56.1(3) . . . . ?
O1' C1' C9' C8' 118.3(3) . . . . ?
C2' C1' C9' C8' -63.7(3) . . . . ?
C7' C8' C9' C1' 63.0(3) . . . . ?
C7' C8' C9' C10' -58.1(4) . . . . ?
C3' O3' C10' O10' -172.8(3) . . . . ?
C3' O3' C10' C9' 10.5(4) . . . . ?
C1' C9' C10' O10' 152.5(3) . . . . ?
C8' C9' C10' O10' -89.5(4) . . . . ?
C1' C9' C10' O3' -30.9(4) . . . . ?
C8' C9' C10' O3' 87.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.981

_refine_diff_density_max         0.30
_refine_diff_density_min         -0.21
_refine_diff_density_rms         0.06

#===END of CIF