# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_bei02
#TrackingRef 'bei02cam.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'compound 5b'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 O3'
_chemical_absolute_configuration syn
_chemical_formula_sum            'C13 H16 O3'
_chemical_formula_weight         220.26

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   5.1378(3)
_cell_length_b                   6.7876(4)
_cell_length_c                   32.2990(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1126.37(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2856
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      30.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  Triumph
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10745
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         30.53
_reflns_number_total             3336
_reflns_number_gt                2856
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_publication_material  ?

_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^)+(0.0473P)^2^+0.2383P] 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'
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_number_reflns         3336
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2774(2) 0.10745(17) 0.09636(3) 0.0137(2) Uani 1 1 d . . .
C1 C 0.1165(3) -0.0529(2) 0.08695(5) 0.0136(3) Uani 1 1 d . . .
O2 O 0.4111(3) -0.38132(19) 0.19221(4) 0.0224(3) Uani 1 1 d . A .
C2 C 0.1525(3) -0.2009(3) 0.11393(5) 0.0132(3) Uani 1 1 d . . .
O3 O 0.3098(2) -0.07661(19) 0.00583(4) 0.0196(3) Uani 1 1 d . . .
C3 C 0.3472(3) -0.1304(3) 0.14289(5) 0.0119(3) Uani 1 1 d . A .
C4 C 0.4629(3) -0.2156(3) 0.18003(5) 0.0162(3) Uani 1 1 d . . .
C5 C 0.6767(6) -0.0905(7) 0.20030(13) 0.0174(7) Uani 0.75 1 d P A 1
H5A H 0.6832 -0.1225 0.2302 0.021 Uiso 0.75 1 calc PR A 1
H5B H 0.8465 -0.1280 0.1881 0.021 Uiso 0.75 1 calc PR A 1
C6 C 0.6417(5) 0.1324(4) 0.19556(7) 0.0142(4) Uani 0.75 1 d P A 1
H6 H 0.4834 0.1718 0.2115 0.017 Uiso 0.75 1 calc PR A 1
C5A C 0.592(2) -0.069(2) 0.2075(4) 0.020(2) Uani 0.25 1 d P A 2
H5A1 H 0.7093 -0.1389 0.2269 0.023 Uiso 0.25 1 calc PR A 2
H5A2 H 0.4582 0.0000 0.2241 0.023 Uiso 0.25 1 calc PR A 2
C6A C 0.7514(13) 0.0843(11) 0.1826(2) 0.0173(15) Uani 0.25 1 d P A 2
H6A H 0.8977 0.0136 0.1685 0.021 Uiso 0.25 1 calc PR A 2
C7 C 0.6002(3) 0.1922(3) 0.15027(5) 0.0162(3) Uani 1 1 d . . .
H7A H 0.5318 0.3284 0.1489 0.019 Uiso 1 1 calc R A 1
H7B H 0.7682 0.1883 0.1353 0.019 Uiso 1 1 calc R A 1
C8 C 0.4137(3) 0.0550(2) 0.13064(5) 0.0124(3) Uani 1 1 d . A .
C9 C 0.0159(3) -0.3947(3) 0.11516(6) 0.0186(4) Uani 1 1 d . . .
H9A H -0.1124 -0.4006 0.0927 0.028 Uiso 1 1 calc R . .
H9B H -0.0725 -0.4097 0.1419 0.028 Uiso 1 1 calc R . .
H9C H 0.1430 -0.5011 0.1117 0.028 Uiso 1 1 calc R . .
C10 C 0.8735(4) 0.2396(3) 0.21392(6) 0.0236(4) Uani 1 1 d . . .
H10A H 0.8377 0.3815 0.2176 0.035 Uiso 1 1 d . . .
H10B H 1.0414 0.2542 0.1972 0.035 Uiso 1 1 d . . .
H10C H 0.9057 0.1954 0.2389 0.035 Uiso 1 1 d . . .
C11 C -0.0542(3) -0.0204(3) 0.05050(5) 0.0152(3) Uani 1 1 d . . .
H11A H -0.1402 0.1093 0.0535 0.018 Uiso 1 1 calc R . .
H11B H -0.1922 -0.1223 0.0505 0.018 Uiso 1 1 calc R . .
C12 C 0.0840(3) -0.0263(2) 0.00904(5) 0.0135(3) Uani 1 1 d . . .
C13 C -0.0750(3) 0.0373(3) -0.02742(5) 0.0192(4) Uani 1 1 d . . .
H13A H -0.0732 0.1813 -0.0294 0.029 Uiso 1 1 calc R . .
H13B H -0.2545 -0.0087 -0.0240 0.029 Uiso 1 1 calc R . .
H13C H -0.0012 -0.0193 -0.0528 0.029 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
O1 0.0181(5) 0.0102(6) 0.0130(5) 0.0006(5) -0.0025(4) -0.0022(5)
C1 0.0144(7) 0.0131(8) 0.0133(7) -0.0029(6) 0.0003(6) -0.0018(6)
O2 0.0342(7) 0.0136(6) 0.0194(6) 0.0049(5) -0.0014(5) 0.0008(6)
C2 0.0144(7) 0.0125(8) 0.0128(7) -0.0030(6) 0.0013(6) 0.0000(6)
O3 0.0164(5) 0.0232(7) 0.0192(6) -0.0015(5) 0.0001(5) 0.0034(5)
C3 0.0140(7) 0.0106(7) 0.0111(7) -0.0013(6) 0.0010(5) 0.0003(6)
C4 0.0208(8) 0.0137(9) 0.0143(8) -0.0002(6) 0.0019(6) 0.0023(7)
C5 0.0178(17) 0.0217(16) 0.0127(17) 0.0012(13) -0.0017(13) 0.0006(16)
C6 0.0122(10) 0.0167(12) 0.0136(10) -0.0031(9) -0.0008(9) 0.0003(9)
C5A 0.021(5) 0.025(6) 0.012(5) 0.004(4) 0.000(4) -0.005(5)
C6A 0.008(3) 0.023(4) 0.021(4) -0.010(3) 0.001(3) 0.005(3)
C7 0.0191(8) 0.0113(8) 0.0183(8) -0.0017(7) -0.0034(7) -0.0031(6)
C8 0.0152(7) 0.0117(8) 0.0102(7) -0.0007(6) -0.0005(6) 0.0014(6)
C9 0.0215(8) 0.0149(9) 0.0194(8) -0.0012(7) 0.0007(7) -0.0052(7)
C10 0.0224(8) 0.0273(10) 0.0211(9) 0.0008(8) -0.0089(8) -0.0098(8)
C11 0.0131(7) 0.0178(9) 0.0147(8) -0.0020(7) -0.0014(6) 0.0023(6)
C12 0.0166(7) 0.0085(7) 0.0153(7) -0.0007(6) -0.0004(6) -0.0006(6)
C13 0.0188(8) 0.0231(9) 0.0158(8) 0.0049(7) -0.0018(6) 0.0034(7)

_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 C8 1.3576(19) . ?
O1 C1 1.4000(19) . ?
C1 C2 1.343(2) . ?
C1 C11 1.484(2) . ?
O2 C4 1.221(2) . ?
C2 C3 1.451(2) . ?
C2 C9 1.491(2) . ?
O3 C12 1.2138(19) . ?
C3 C8 1.363(2) . ?
C3 C4 1.459(2) . ?
C4 C5A 1.489(14) . ?
C4 C5 1.535(5) . ?
C5 C6 1.531(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C10 1.517(3) . ?
C6 C7 1.533(3) . ?
C6 H6 1.0000 . ?
C5A C6A 1.551(15) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A C7 1.493(7) . ?
C6A C10 1.591(7) . ?
C6A H6A 1.0000 . ?
C7 C8 1.479(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9877 . ?
C10 H10B 1.0225 . ?
C10 H10C 0.8765 . ?
C11 C12 1.516(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.497(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C8 O1 C1 106.13(12) . . ?
C2 C1 O1 111.07(13) . . ?
C2 C1 C11 134.99(15) . . ?
O1 C1 C11 113.93(14) . . ?
C1 C2 C3 105.45(14) . . ?
C1 C2 C9 127.76(15) . . ?
C3 C2 C9 126.76(15) . . ?
C8 C3 C2 106.89(14) . . ?
C8 C3 C4 120.19(15) . . ?
C2 C3 C4 132.88(16) . . ?
O2 C4 C3 122.79(16) . . ?
O2 C4 C5A 121.4(5) . . ?
C3 C4 C5A 114.0(6) . . ?
O2 C4 C5 121.9(2) . . ?
C3 C4 C5 115.0(2) . . ?
C5A C4 C5 19.5(3) . . ?
C6 C5 C4 114.8(3) . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.5 . . ?
C10 C6 C5 110.1(2) . . ?
C10 C6 C7 110.81(18) . . ?
C5 C6 C7 111.9(2) . . ?
C10 C6 H6 108.0 . . ?
C5 C6 H6 108.0 . . ?
C7 C6 H6 108.0 . . ?
C4 C5A C6A 112.0(8) . . ?
C4 C5A H5A1 109.2 . . ?
C6A C5A H5A1 109.2 . . ?
C4 C5A H5A2 109.2 . . ?
C6A C5A H5A2 109.2 . . ?
H5A1 C5A H5A2 107.9 . . ?
C7 C6A C5A 114.7(6) . . ?
C7 C6A C10 109.0(5) . . ?
C5A C6A C10 108.8(7) . . ?
C7 C6A H6A 108.1 . . ?
C5A C6A H6A 108.1 . . ?
C10 C6A H6A 108.1 . . ?
C8 C7 C6A 109.1(3) . . ?
C8 C7 C6 109.41(15) . . ?
C6A C7 C6 29.6(3) . . ?
C8 C7 H7A 109.8 . . ?
C6A C7 H7A 132.4 . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C6A C7 H7B 82.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
O1 C8 C3 110.46(14) . . ?
O1 C8 C7 121.26(14) . . ?
C3 C8 C7 128.28(15) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C6A 28.7(2) . . ?
C6 C10 H10A 111.6 . . ?
C6A C10 H10A 130.5 . . ?
C6 C10 H10B 120.2 . . ?
C6A C10 H10B 93.5 . . ?
H10A C10 H10B 97.3 . . ?
C6 C10 H10C 110.1 . . ?
C6A C10 H10C 115.7 . . ?
H10A C10 H10C 105.0 . . ?
H10B C10 H10C 111.1 . . ?
C1 C11 C12 114.81(13) . . ?
C1 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C1 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
O3 C12 C13 122.37(15) . . ?
O3 C12 C11 122.04(15) . . ?
C13 C12 C11 115.58(13) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C8 O1 C1 C2 -0.68(17) . . . . ?
C8 O1 C1 C11 178.55(13) . . . . ?
O1 C1 C2 C3 0.66(18) . . . . ?
C11 C1 C2 C3 -178.33(17) . . . . ?
O1 C1 C2 C9 178.69(15) . . . . ?
C11 C1 C2 C9 -0.3(3) . . . . ?
C1 C2 C3 C8 -0.41(18) . . . . ?
C9 C2 C3 C8 -178.46(15) . . . . ?
C1 C2 C3 C4 177.14(17) . . . . ?
C9 C2 C3 C4 -0.9(3) . . . . ?
C8 C3 C4 O2 -179.57(16) . . . . ?
C2 C3 C4 O2 3.1(3) . . . . ?
C8 C3 C4 C5A 15.7(5) . . . . ?
C2 C3 C4 C5A -161.6(4) . . . . ?
C8 C3 C4 C5 -5.7(2) . . . . ?
C2 C3 C4 C5 177.0(2) . . . . ?
O2 C4 C5 C6 -154.4(2) . . . . ?
C3 C4 C5 C6 31.7(3) . . . . ?
C5A C4 C5 C6 -59.9(19) . . . . ?
C4 C5 C6 C10 -175.8(2) . . . . ?
C4 C5 C6 C7 -52.1(3) . . . . ?
O2 C4 C5A C6A 153.2(6) . . . . ?
C3 C4 C5A C6A -41.9(8) . . . . ?
C5 C4 C5A C6A 55.5(16) . . . . ?
C4 C5A C6A C7 55.5(10) . . . . ?
C4 C5A C6A C10 177.8(6) . . . . ?
C5A C6A C7 C8 -37.7(8) . . . . ?
C10 C6A C7 C8 -159.9(3) . . . . ?
C5A C6A C7 C6 58.1(7) . . . . ?
C10 C6A C7 C6 -64.1(5) . . . . ?
C10 C6 C7 C8 167.47(17) . . . . ?
C5 C6 C7 C8 44.2(2) . . . . ?
C10 C6 C7 C6A 72.7(6) . . . . ?
C5 C6 C7 C6A -50.6(6) . . . . ?
C1 O1 C8 C3 0.39(17) . . . . ?
C1 O1 C8 C7 -178.39(14) . . . . ?
C2 C3 C8 O1 0.00(18) . . . . ?
C4 C3 C8 O1 -177.92(14) . . . . ?
C2 C3 C8 C7 178.68(15) . . . . ?
C4 C3 C8 C7 0.8(3) . . . . ?
C6A C7 C8 O1 -170.7(3) . . . . ?
C6 C7 C8 O1 157.87(16) . . . . ?
C6A C7 C8 C3 10.8(4) . . . . ?
C6 C7 C8 C3 -20.7(3) . . . . ?
C5 C6 C10 C6A 57.3(6) . . . . ?
C7 C6 C10 C6A -67.0(6) . . . . ?
C7 C6A C10 C6 69.2(5) . . . . ?
C5A C6A C10 C6 -56.5(7) . . . . ?
C2 C1 C11 C12 -107.4(2) . . . . ?
O1 C1 C11 C12 73.58(18) . . . . ?
C1 C11 C12 O3 8.3(2) . . . . ?
C1 C11 C12 C13 -170.73(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        30.53
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 926712'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_bei04a
#TrackingRef 'bei04cam.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'compound 5d'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 O3'
_chemical_formula_sum            'C14 H18 O3'
_chemical_formula_weight         234.28

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           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   22.603(4)
_cell_length_b                   11.0296(19)
_cell_length_c                   10.1777(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2537.3(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2839
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      25.08

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  Triumph
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14805
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_sigmaI/netI    0.0961
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.08
_reflns_number_total             4435
_reflns_number_gt                2839
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_publication_material  ?

_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^)+(0.0539P)^2^+0.0000P] 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'
_refine_ls_abs_structure_Flack   -0.1(19)
_refine_ls_number_reflns         4435
_refine_ls_number_parameters     344
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.045
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O -0.08573(14) 0.5367(3) -0.2947(3) 0.0293(8) Uani 1 1 d . A .
C1A C -0.0375(2) 0.5532(4) -0.2447(4) 0.0281(11) Uani 1 1 d . . .
O2A O 0.03255(10) 0.7489(2) -0.0101(2) 0.0199(6) Uani 1 1 d . A .
O3A O -0.00810(17) 1.0279(3) -0.0862(3) 0.0289(8) Uani 1 1 d . . .
C3A C 0.0705(2) 0.4835(4) -0.2182(5) 0.0230(13) Uani 1 1 d . . .
C2A C 0.0167(4) 0.5015(7) -0.3089(10) 0.020(3) Uani 0.58 1 d PU A 1
H2A1 H 0.0285 0.5560 -0.3817 0.024 Uiso 0.58 1 calc PR A 1
H2A2 H 0.0063 0.4222 -0.3479 0.024 Uiso 0.58 1 calc PR A 1
C12A C 0.0468(4) 0.3818(7) -0.1123(8) 0.029(2) Uani 0.58 1 d PU A 1
H12X H 0.0125 0.4140 -0.0649 0.044 Uiso 0.58 1 calc PR A 1
H12Y H 0.0784 0.3629 -0.0497 0.044 Uiso 0.58 1 calc PR A 1
H12Z H 0.0353 0.3079 -0.1594 0.044 Uiso 0.58 1 calc PR A 1
C13A C 0.1216(4) 0.4277(8) -0.2861(8) 0.034(2) Uani 0.58 1 d PU A 1
H13X H 0.1086 0.3544 -0.3322 0.051 Uiso 0.58 1 calc PR A 1
H13Y H 0.1520 0.4064 -0.2214 0.051 Uiso 0.58 1 calc PR A 1
H13Z H 0.1380 0.4854 -0.3496 0.051 Uiso 0.58 1 calc PR A 1
C2C C 0.0097(4) 0.4418(9) -0.2374(10) 0.021(2) Uani 0.42 1 d PU A 2
H2C1 H -0.0013 0.3874 -0.1640 0.025 Uiso 0.42 1 calc PR A 2
H2C2 H 0.0075 0.3943 -0.3198 0.025 Uiso 0.42 1 calc PR A 2
C12C C 0.0921(4) 0.5532(9) -0.3548(9) 0.029(2) Uani 0.42 1 d PU A 2
H12D H 0.0875 0.4982 -0.4298 0.044 Uiso 0.42 1 calc PR A 2
H12E H 0.1338 0.5767 -0.3466 0.044 Uiso 0.42 1 calc PR A 2
H12F H 0.0679 0.6257 -0.3687 0.044 Uiso 0.42 1 calc PR A 2
C13C C 0.1140(5) 0.3741(10) -0.2142(10) 0.029(3) Uani 0.42 1 d PU A 2
H13D H 0.1069 0.3266 -0.1344 0.043 Uiso 0.42 1 calc PR A 2
H13E H 0.1548 0.4040 -0.2143 0.043 Uiso 0.42 1 calc PR A 2
H13F H 0.1076 0.3228 -0.2916 0.043 Uiso 0.42 1 calc PR A 2
C4A C 0.08379(19) 0.5854(4) -0.1287(5) 0.0360(12) Uani 1 1 d . A .
H4A1 H 0.1009 0.5533 -0.0462 0.043 Uiso 1 1 calc R . .
H4A2 H 0.1137 0.6388 -0.1701 0.043 Uiso 1 1 calc R . .
C5A C 0.03095(19) 0.6565(4) -0.0981(4) 0.0205(11) Uani 1 1 d . . .
C6A C -0.02491(17) 0.6443(4) -0.1462(4) 0.0194(10) Uani 1 1 d . A .
C7A C -0.06141(17) 0.7326(3) -0.0825(4) 0.0187(9) Uani 1 1 d . . .
C8A C -0.02556(17) 0.7935(3) -0.0005(4) 0.0179(9) Uani 1 1 d . A .
C9A C -0.0330(2) 0.8968(4) 0.0915(4) 0.0209(12) Uani 1 1 d . . .
H9A1 H -0.0062 0.8848 0.1674 0.025 Uiso 1 1 calc R A .
H9A2 H -0.0741 0.8963 0.1252 0.025 Uiso 1 1 calc R . .
C10A C -0.0205(2) 1.0194(4) 0.0315(6) 0.0200(13) Uani 1 1 d U A .
C11A C -0.0231(2) 1.1247(4) 0.1204(4) 0.0249(12) Uani 1 1 d . . .
H11A H -0.0075 1.1964 0.0753 0.037 Uiso 1 1 calc R A .
H11B H 0.0007 1.1083 0.1989 0.037 Uiso 1 1 calc R . .
H11C H -0.0642 1.1394 0.1463 0.037 Uiso 1 1 calc R . .
C14A C -0.1261(2) 0.7538(4) -0.1019(5) 0.0266(11) Uani 1 1 d . A .
H14A H -0.1408 0.8080 -0.0329 0.040 Uiso 1 1 calc R . .
H14B H -0.1472 0.6763 -0.0973 0.040 Uiso 1 1 calc R . .
H14C H -0.1327 0.7910 -0.1880 0.040 Uiso 1 1 calc R . .
O1B O 0.15988(14) 0.9653(3) 0.5491(3) 0.0282(8) Uani 1 1 d . . .
C1B C 0.20952(19) 0.9427(4) 0.5058(4) 0.0222(10) Uani 1 1 d . . .
O2B O 0.27954(11) 0.7558(2) 0.2601(3) 0.0211(7) Uani 1 1 d . . .
C2B C 0.2640(2) 1.0021(3) 0.5637(5) 0.0191(15) Uani 1 1 d . . .
H2B1 H 0.2789 0.9504 0.6359 0.023 Uiso 1 1 calc R . .
H2B2 H 0.2522 1.0808 0.6025 0.023 Uiso 1 1 calc R . .
O3B O 0.23738(16) 0.4840(3) 0.3337(4) 0.0302(10) Uani 1 1 d . . .
C3B C 0.3150(2) 1.0247(4) 0.4668(5) 0.0233(12) Uani 1 1 d . . .
C4B C 0.33165(19) 0.9063(4) 0.3978(4) 0.0246(10) Uani 1 1 d . . .
H4B1 H 0.3564 0.9241 0.3198 0.030 Uiso 1 1 calc R . .
H4B2 H 0.3549 0.8545 0.4582 0.030 Uiso 1 1 calc R . .
C5B C 0.27765(18) 0.8425(4) 0.3573(4) 0.0200(11) Uani 1 1 d . . .
C6B C 0.22149(18) 0.8561(4) 0.4019(4) 0.0198(10) Uani 1 1 d . . .
C7B C 0.18429(17) 0.7730(4) 0.3283(4) 0.0215(10) Uani 1 1 d . . .
C8B C 0.22137(19) 0.7142(4) 0.2453(4) 0.0231(10) Uani 1 1 d . . .
C9B C 0.21384(19) 0.6126(4) 0.1547(4) 0.0203(12) Uani 1 1 d . . .
H9B1 H 0.2406 0.6236 0.0787 0.024 Uiso 1 1 calc R . .
H9B2 H 0.1727 0.6123 0.1214 0.024 Uiso 1 1 calc R . .
C10B C 0.2269(2) 0.4916(3) 0.2194(6) 0.0152(13) Uani 1 1 d U . .
C11B C 0.2225(2) 0.3835(4) 0.1322(5) 0.0223(12) Uani 1 1 d U . .
H11D H 0.2360 0.3114 0.1800 0.033 Uiso 1 1 calc R . .
H11E H 0.2475 0.3957 0.0545 0.033 Uiso 1 1 calc R . .
H11F H 0.1814 0.3723 0.1047 0.033 Uiso 1 1 calc R . .
C12B C 0.2952(2) 1.1217(4) 0.3660(4) 0.0295(13) Uani 1 1 d . . .
H12A H 0.2906 1.2000 0.4105 0.044 Uiso 1 1 calc R . .
H12B H 0.2573 1.0977 0.3271 0.044 Uiso 1 1 calc R . .
H12C H 0.3251 1.1289 0.2967 0.044 Uiso 1 1 calc R . .
C13B C 0.3686(2) 1.0727(4) 0.5408(5) 0.0352(12) Uani 1 1 d . . .
H13A H 0.3591 1.1519 0.5790 0.053 Uiso 1 1 calc R . .
H13B H 0.4019 1.0811 0.4801 0.053 Uiso 1 1 calc R . .
H13C H 0.3791 1.0159 0.6111 0.053 Uiso 1 1 calc R . .
C14B C 0.1192(2) 0.7557(5) 0.3445(5) 0.0383(15) Uani 1 1 d . . .
H14D H 0.1052 0.6951 0.2813 0.057 Uiso 1 1 calc R . .
H14E H 0.0988 0.8328 0.3288 0.057 Uiso 1 1 calc R . .
H14F H 0.1108 0.7278 0.4340 0.057 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 0.019(2) 0.043(2) 0.0264(17) -0.012(2) -0.0062(16) -0.0036(18)
C1A 0.026(3) 0.031(3) 0.028(2) -0.013(2) 0.002(2) 0.003(2)
O2A 0.0216(16) 0.0178(14) 0.0202(14) -0.0032(13) -0.0021(13) -0.0032(14)
O3A 0.035(2) 0.0309(18) 0.021(2) 0.0052(17) 0.0060(17) -0.0023(17)
C3A 0.026(3) 0.024(3) 0.019(3) -0.006(2) -0.011(2) 0.007(2)
C2A 0.016(5) 0.019(5) 0.024(5) -0.003(3) -0.002(4) -0.005(3)
C12A 0.037(4) 0.020(4) 0.030(4) 0.000(3) -0.014(4) 0.015(4)
C13A 0.028(4) 0.034(5) 0.039(4) -0.016(4) 0.005(4) 0.004(4)
C2C 0.028(5) 0.012(4) 0.022(4) -0.004(4) 0.001(4) -0.001(4)
C12C 0.028(5) 0.028(5) 0.032(4) 0.002(4) 0.006(4) 0.000(4)
C13C 0.025(5) 0.030(5) 0.031(5) 0.001(4) 0.000(4) 0.002(4)
C4A 0.020(3) 0.040(3) 0.048(3) -0.018(2) 0.002(2) 0.000(2)
C5A 0.021(3) 0.022(3) 0.019(2) -0.006(2) -0.003(2) -0.006(2)
C6A 0.019(2) 0.021(2) 0.018(2) -0.0018(19) 0.0015(19) -0.002(2)
C7A 0.022(2) 0.013(2) 0.021(2) 0.0027(19) -0.0049(18) -0.003(2)
C8A 0.017(2) 0.015(2) 0.022(2) 0.004(2) -0.0001(19) 0.0009(19)
C9A 0.019(3) 0.021(3) 0.022(2) -0.009(2) 0.001(2) 0.000(2)
C10A 0.008(2) 0.028(3) 0.024(3) 0.003(2) -0.006(2) 0.002(2)
C11A 0.029(3) 0.016(3) 0.029(3) 0.002(2) 0.003(2) 0.001(2)
C14A 0.023(2) 0.019(2) 0.038(3) -0.004(2) -0.003(2) 0.0058(19)
O1B 0.0213(19) 0.0343(17) 0.0291(17) -0.0041(19) 0.0039(16) 0.0004(18)
C1B 0.020(3) 0.023(3) 0.023(2) 0.001(2) 0.004(2) 0.004(2)
O2B 0.0224(17) 0.0157(15) 0.0252(15) -0.0072(13) 0.0011(12) -0.0003(13)
C2B 0.027(3) 0.018(3) 0.013(3) -0.0024(17) 0.002(3) 0.0066(19)
O3B 0.030(2) 0.042(2) 0.019(2) 0.0005(15) -0.0053(16) 0.0027(16)
C3B 0.014(3) 0.029(2) 0.027(3) -0.012(3) 0.000(2) -0.001(2)
C4B 0.021(3) 0.024(3) 0.029(2) -0.007(2) 0.001(2) 0.003(2)
C5B 0.025(3) 0.016(2) 0.020(2) -0.002(2) 0.000(2) 0.005(2)
C6B 0.017(2) 0.017(2) 0.025(2) 0.001(2) 0.0001(19) 0.001(2)
C7B 0.020(2) 0.022(2) 0.023(2) -0.001(2) 0.002(2) -0.004(2)
C8B 0.021(2) 0.021(3) 0.028(2) -0.002(2) -0.0023(19) -0.002(2)
C9B 0.030(3) 0.010(3) 0.020(2) 0.000(2) -0.005(2) 0.005(2)
C10B 0.013(3) 0.013(3) 0.019(3) -0.0027(17) 0.000(2) 0.0027(17)
C11B 0.026(3) 0.014(2) 0.027(2) -0.002(2) -0.001(2) 0.001(2)
C12B 0.042(3) 0.028(3) 0.019(2) -0.006(2) 0.000(2) -0.010(3)
C13B 0.025(3) 0.035(3) 0.045(3) -0.016(3) -0.004(2) -0.003(2)
C14B 0.026(3) 0.031(3) 0.058(4) -0.020(3) 0.011(3) -0.006(2)

_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 C1A 1.217(5) . ?
C1A C6A 1.449(6) . ?
C1A C2A 1.500(9) . ?
C1A C2C 1.629(10) . ?
O2A C5A 1.357(5) . ?
O2A C8A 1.406(4) . ?
O3A C10A 1.234(6) . ?
C3A C2C 1.463(11) . ?
C3A C4A 1.477(6) . ?
C3A C13A 1.479(9) . ?
C3A C2A 1.539(10) . ?
C3A C13C 1.557(11) . ?
C3A C12A 1.645(9) . ?
C3A C12C 1.663(10) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C12A H12X 0.9800 . ?
C12A H12Y 0.9800 . ?
C12A H12Z 0.9800 . ?
C13A H13X 0.9800 . ?
C13A H13Y 0.9800 . ?
C13A H13Z 0.9800 . ?
C2C H2C1 0.9900 . ?
C2C H2C2 0.9900 . ?
C12C H12D 0.9800 . ?
C12C H12E 0.9800 . ?
C12C H12F 0.9800 . ?
C13C H13D 0.9800 . ?
C13C H13E 0.9800 . ?
C13C H13F 0.9800 . ?
C4A C5A 1.462(6) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6A 1.361(5) . ?
C6A C7A 1.431(5) . ?
C7A C8A 1.343(5) . ?
C7A C14A 1.493(6) . ?
C8A C9A 1.485(5) . ?
C9A C10A 1.511(6) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C11A 1.474(7) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
O1B C1B 1.231(5) . ?
C1B C6B 1.451(6) . ?
C1B C2B 1.514(6) . ?
O2B C5B 1.377(5) . ?
O2B C8B 1.401(4) . ?
C2B C3B 1.536(7) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
O3B C10B 1.190(7) . ?
C3B C13B 1.522(6) . ?
C3B C4B 1.529(6) . ?
C3B C12B 1.548(7) . ?
C4B C5B 1.468(6) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5B C6B 1.356(5) . ?
C6B C7B 1.452(5) . ?
C7B C8B 1.355(5) . ?
C7B C14B 1.493(6) . ?
C8B C9B 1.461(6) . ?
C9B C10B 1.517(6) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C11B 1.489(6) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12A 0.9800 . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
C13B H13A 0.9800 . ?
C13B H13B 0.9800 . ?
C13B H13C 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 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
O1A C1A C6A 124.7(4) . . ?
O1A C1A C2A 119.6(5) . . ?
C6A C1A C2A 113.9(5) . . ?
O1A C1A C2C 119.6(5) . . ?
C6A C1A C2C 111.3(5) . . ?
C2A C1A C2C 36.8(4) . . ?
C5A O2A C8A 106.5(3) . . ?
C2C C3A C4A 120.9(5) . . ?
C2C C3A C13A 122.7(6) . . ?
C4A C3A C13A 116.5(5) . . ?
C2C C3A C2A 38.6(5) . . ?
C4A C3A C2A 115.6(4) . . ?
C13A C3A C2A 112.9(6) . . ?
C2C C3A C13C 110.7(6) . . ?
C4A C3A C13C 116.5(5) . . ?
C13A C3A C13C 36.6(4) . . ?
C2A C3A C13C 127.9(6) . . ?
C2C C3A C12A 64.3(5) . . ?
C4A C3A C12A 100.5(5) . . ?
C13A C3A C12A 106.1(5) . . ?
C2A C3A C12A 102.9(6) . . ?
C13C C3A C12A 70.1(5) . . ?
C2C C3A C12C 108.1(6) . . ?
C4A C3A C12C 96.0(5) . . ?
C13A C3A C12C 64.6(6) . . ?
C2A C3A C12C 70.8(5) . . ?
C13C C3A C12C 101.2(6) . . ?
C12A C3A C12C 163.5(5) . . ?
C1A C2A C3A 115.7(7) . . ?
C1A C2A H2A1 108.4 . . ?
C3A C2A H2A1 108.4 . . ?
C1A C2A H2A2 108.4 . . ?
C3A C2A H2A2 108.4 . . ?
H2A1 C2A H2A2 107.4 . . ?
C3A C12A H12X 109.5 . . ?
C3A C12A H12Y 109.5 . . ?
C3A C12A H12Z 109.5 . . ?
C3A C13A H13X 109.5 . . ?
C3A C13A H13Y 109.5 . . ?
C3A C13A H13Z 109.5 . . ?
C3A C2C C1A 112.6(6) . . ?
C3A C2C H2C1 109.1 . . ?
C1A C2C H2C1 109.1 . . ?
C3A C2C H2C2 109.1 . . ?
C1A C2C H2C2 109.1 . . ?
H2C1 C2C H2C2 107.8 . . ?
C3A C12C H12D 109.5 . . ?
C3A C12C H12E 109.5 . . ?
H12D C12C H12E 109.5 . . ?
C3A C12C H12F 109.5 . . ?
H12D C12C H12F 109.5 . . ?
H12E C12C H12F 109.5 . . ?
C3A C13C H13D 109.5 . . ?
C3A C13C H13E 109.5 . . ?
H13D C13C H13E 109.5 . . ?
C3A C13C H13F 109.5 . . ?
H13D C13C H13F 109.5 . . ?
H13E C13C H13F 109.5 . . ?
C5A C4A C3A 111.9(4) . . ?
C5A C4A H4A1 109.2 . . ?
C3A C4A H4A1 109.2 . . ?
C5A C4A H4A2 109.2 . . ?
C3A C4A H4A2 109.2 . . ?
H4A1 C4A H4A2 107.9 . . ?
O2A C5A C6A 109.6(4) . . ?
O2A C5A C4A 121.4(4) . . ?
C6A C5A C4A 128.9(4) . . ?
C5A C6A C7A 107.8(4) . . ?
C5A C6A C1A 120.0(4) . . ?
C7A C6A C1A 132.3(4) . . ?
C8A C7A C6A 105.9(3) . . ?
C8A C7A C14A 126.4(4) . . ?
C6A C7A C14A 127.7(4) . . ?
C7A C8A O2A 110.2(3) . . ?
C7A C8A C9A 135.0(4) . . ?
O2A C8A C9A 114.7(3) . . ?
C8A C9A C10A 114.2(4) . . ?
C8A C9A H9A1 108.7 . . ?
C10A C9A H9A1 108.7 . . ?
C8A C9A H9A2 108.7 . . ?
C10A C9A H9A2 108.7 . . ?
H9A1 C9A H9A2 107.6 . . ?
O3A C10A C11A 123.1(5) . . ?
O3A C10A C9A 120.2(5) . . ?
C11A C10A C9A 116.7(5) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C7A C14A H14A 109.5 . . ?
C7A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C7A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
O1B C1B C6B 124.4(4) . . ?
O1B C1B C2B 121.0(4) . . ?
C6B C1B C2B 114.6(4) . . ?
C5B O2B C8B 106.0(3) . . ?
C1B C2B C3B 115.5(4) . . ?
C1B C2B H2B1 108.4 . . ?
C3B C2B H2B1 108.4 . . ?
C1B C2B H2B2 108.4 . . ?
C3B C2B H2B2 108.4 . . ?
H2B1 C2B H2B2 107.5 . . ?
C13B C3B C4B 109.1(4) . . ?
C13B C3B C2B 109.6(4) . . ?
C4B C3B C2B 110.0(4) . . ?
C13B C3B C12B 108.5(4) . . ?
C4B C3B C12B 110.9(4) . . ?
C2B C3B C12B 108.7(4) . . ?
C5B C4B C3B 109.5(4) . . ?
C5B C4B H4B1 109.8 . . ?
C3B C4B H4B1 109.8 . . ?
C5B C4B H4B2 109.8 . . ?
C3B C4B H4B2 109.8 . . ?
H4B1 C4B H4B2 108.2 . . ?
C6B C5B O2B 110.3(4) . . ?
C6B C5B C4B 129.1(4) . . ?
O2B C5B C4B 120.6(4) . . ?
C5B C6B C1B 119.4(4) . . ?
C5B C6B C7B 107.4(4) . . ?
C1B C6B C7B 133.1(4) . . ?
C8B C7B C6B 105.4(3) . . ?
C8B C7B C14B 128.1(4) . . ?
C6B C7B C14B 126.5(4) . . ?
C7B C8B O2B 110.9(3) . . ?
C7B C8B C9B 133.5(4) . . ?
O2B C8B C9B 115.4(4) . . ?
C8B C9B C10B 112.2(4) . . ?
C8B C9B H9B1 109.2 . . ?
C10B C9B H9B1 109.2 . . ?
C8B C9B H9B2 109.2 . . ?
C10B C9B H9B2 109.2 . . ?
H9B1 C9B H9B2 107.9 . . ?
O3B C10B C11B 122.7(4) . . ?
O3B C10B C9B 121.6(4) . . ?
C11B C10B C9B 115.6(5) . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C3B C12B H12A 109.5 . . ?
C3B C12B H12B 109.5 . . ?
H12A C12B H12B 109.5 . . ?
C3B C12B H12C 109.5 . . ?
H12A C12B H12C 109.5 . . ?
H12B C12B H12C 109.5 . . ?
C3B C13B H13A 109.5 . . ?
C3B C13B H13B 109.5 . . ?
H13A C13B H13B 109.5 . . ?
C3B C13B H13C 109.5 . . ?
H13A C13B H13C 109.5 . . ?
H13B C13B H13C 109.5 . . ?
C7B C14B H14D 109.5 . . ?
C7B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C7B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C2A C3A -157.7(5) . . . . ?
C6A C1A C2A C3A 37.3(8) . . . . ?
C2C C1A C2A C3A -56.8(8) . . . . ?
C2C C3A C2A C1A 63.4(8) . . . . ?
C4A C3A C2A C1A -44.7(8) . . . . ?
C13A C3A C2A C1A 177.6(6) . . . . ?
C13C C3A C2A C1A 138.5(7) . . . . ?
C12A C3A C2A C1A 63.7(7) . . . . ?
C12C C3A C2A C1A -132.2(7) . . . . ?
C4A C3A C2C C1A 39.7(9) . . . . ?
C13A C3A C2C C1A -140.0(7) . . . . ?
C2A C3A C2C C1A -53.6(8) . . . . ?
C13C C3A C2C C1A -179.0(6) . . . . ?
C12A C3A C2C C1A 126.7(8) . . . . ?
C12C C3A C2C C1A -69.1(8) . . . . ?
O1A C1A C2C C3A 160.2(6) . . . . ?
C6A C1A C2C C3A -42.4(8) . . . . ?
C2A C1A C2C C3A 59.3(8) . . . . ?
C2C C3A C4A C5A -16.9(8) . . . . ?
C13A C3A C4A C5A 162.8(6) . . . . ?
C2A C3A C4A C5A 26.7(7) . . . . ?
C13C C3A C4A C5A -156.1(6) . . . . ?
C12A C3A C4A C5A -83.2(5) . . . . ?
C12C C3A C4A C5A 98.2(5) . . . . ?
C8A O2A C5A C6A 1.9(4) . . . . ?
C8A O2A C5A C4A -177.6(4) . . . . ?
C3A C4A C5A O2A 175.2(4) . . . . ?
C3A C4A C5A C6A -4.2(7) . . . . ?
O2A C5A C6A C7A -1.5(5) . . . . ?
C4A C5A C6A C7A 178.0(5) . . . . ?
O2A C5A C6A C1A 178.4(4) . . . . ?
C4A C5A C6A C1A -2.1(7) . . . . ?
O1A C1A C6A C5A -178.9(5) . . . . ?
C2A C1A C6A C5A -14.8(7) . . . . ?
C2C C1A C6A C5A 25.0(7) . . . . ?
O1A C1A C6A C7A 0.9(8) . . . . ?
C2A C1A C6A C7A 165.0(6) . . . . ?
C2C C1A C6A C7A -155.1(6) . . . . ?
C5A C6A C7A C8A 0.5(5) . . . . ?
C1A C6A C7A C8A -179.4(4) . . . . ?
C5A C6A C7A C14A -179.5(4) . . . . ?
C1A C6A C7A C14A 0.6(7) . . . . ?
C6A C7A C8A O2A 0.7(4) . . . . ?
C14A C7A C8A O2A -179.4(4) . . . . ?
C6A C7A C8A C9A 178.2(4) . . . . ?
C14A C7A C8A C9A -1.8(7) . . . . ?
C5A O2A C8A C7A -1.6(4) . . . . ?
C5A O2A C8A C9A -179.7(3) . . . . ?
C7A C8A C9A C10A -91.7(6) . . . . ?
O2A C8A C9A C10A 85.7(4) . . . . ?
C8A C9A C10A O3A 3.3(7) . . . . ?
C8A C9A C10A C11A -175.9(4) . . . . ?
O1B C1B C2B C3B -148.4(4) . . . . ?
C6B C1B C2B C3B 34.0(5) . . . . ?
C1B C2B C3B C13B -174.4(4) . . . . ?
C1B C2B C3B C4B -54.4(5) . . . . ?
C1B C2B C3B C12B 67.2(5) . . . . ?
C13B C3B C4B C5B 164.5(4) . . . . ?
C2B C3B C4B C5B 44.3(5) . . . . ?
C12B C3B C4B C5B -76.0(5) . . . . ?
C8B O2B C5B C6B -0.2(4) . . . . ?
C8B O2B C5B C4B -179.6(4) . . . . ?
C3B C4B C5B C6B -19.6(7) . . . . ?
C3B C4B C5B O2B 159.6(4) . . . . ?
O2B C5B C6B C1B 179.5(3) . . . . ?
C4B C5B C6B C1B -1.2(7) . . . . ?
O2B C5B C6B C7B -0.2(5) . . . . ?
C4B C5B C6B C7B 179.0(4) . . . . ?
O1B C1B C6B C5B 176.9(4) . . . . ?
C2B C1B C6B C5B -5.6(6) . . . . ?
O1B C1B C6B C7B -3.4(7) . . . . ?
C2B C1B C6B C7B 174.1(4) . . . . ?
C5B C6B C7B C8B 0.6(5) . . . . ?
C1B C6B C7B C8B -179.1(4) . . . . ?
C5B C6B C7B C14B 179.5(4) . . . . ?
C1B C6B C7B C14B -0.2(7) . . . . ?
C6B C7B C8B O2B -0.8(4) . . . . ?
C14B C7B C8B O2B -179.6(4) . . . . ?
C6B C7B C8B C9B 173.1(4) . . . . ?
C14B C7B C8B C9B -5.7(8) . . . . ?
C5B O2B C8B C7B 0.7(4) . . . . ?
C5B O2B C8B C9B -174.5(4) . . . . ?
C7B C8B C9B C10B -90.8(6) . . . . ?
O2B C8B C9B C10B 82.9(5) . . . . ?
C8B C9B C10B O3B 5.3(7) . . . . ?
C8B C9B C10B C11B -177.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058


_database_code_depnum_ccdc_archive 'CCDC 926713'