# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  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.
#
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#  fide research purposes only. It may contain copyright material
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#  from this site to visualise CIF-encoded structures and 
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data_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 O6'
_chemical_formula_sum            'C14 H22 O6'
_chemical_formula_weight         286.31

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.8616(9)
_cell_length_b                   8.0284(8)
_cell_length_c                   9.9965(8)
_cell_angle_alpha                90
_cell_angle_beta                 118.639(5)
_cell_angle_gamma                90
_cell_volume                     694.62(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3915
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      26.8

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS. Apex II release 2010, Bruker AXS, Inc.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17157
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.321
_diffrn_reflns_theta_max         27.266
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3120
_reflns_number_gt                2541
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_chemical_absolute_configuration syn



_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'












_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.0581P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.6(14)
_refine_ls_number_reflns         3120
_refine_ls_number_parameters     270
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3397(4) 0.5205(4) 0.1004(3) 0.0114(6) Uani 1 1 d . . . . .
C2 C 0.4176(4) 0.3608(4) 0.0866(3) 0.0118(6) Uani 1 1 d . . . . .
C3 C 0.2992(4) 0.2194(4) 0.0136(3) 0.0152(7) Uani 1 1 d . . . . .
C4 C 0.2895(4) 0.0977(4) 0.1218(4) 0.0162(7) Uani 1 1 d . . . . .
C5 C 0.3813(4) 0.0987(4) 0.2702(4) 0.0162(7) Uani 1 1 d . . . . .
C6 C 0.5048(4) 0.2269(4) 0.3484(3) 0.0144(7) Uani 1 1 d . . . . .
C7 C 0.5559(3) 0.3060(4) 0.2407(3) 0.0112(6) Uani 1 1 d . . . . .
C8 C 0.6576(3) 0.4584(4) 0.3095(3) 0.0111(6) Uani 1 1 d . . . . .
C9 C 0.8837(4) 0.5604(4) 0.5258(4) 0.0154(7) Uani 1 1 d . . . . .
C10 C 0.6796(4) 0.7546(4) 0.3780(4) 0.0147(7) Uani 1 1 d . . . . .
C11 C 0.5685(4) 0.6095(4) 0.3156(3) 0.0125(6) Uani 1 1 d . . . . .
C12 C 0.1662(5) 0.6169(5) 0.1824(5) 0.0288(9) Uani 1 1 d . . . . .
C13 C 0.9800(4) 0.5801(5) 0.4452(4) 0.0189(7) Uani 1 1 d . . . . .
C14 C 0.9839(4) 0.5204(5) 0.6927(4) 0.0198(7) Uani 1 1 d . . . . .
O1 O 0.4478(2) 0.6521(3) 0.1669(2) 0.0127(5) Uani 1 1 d . . . . .
O2 O 0.7750(2) 0.4252(3) 0.4627(2) 0.0132(5) Uani 1 1 d . . . . .
O3 O 0.8045(2) 0.7096(3) 0.5241(2) 0.0158(5) Uani 1 1 d . . . . .
O4 O 0.2624(3) 0.4847(3) 0.1827(2) 0.0163(5) Uani 1 1 d . . . . .
O5 O 0.4733(3) 0.4103(3) -0.0160(2) 0.0132(5) Uani 1 1 d . . . . .
O6 O 0.6480(2) 0.1907(3) 0.2094(2) 0.0146(5) Uani 1 1 d . . . . .
H1 H 0.268(4) 0.571(5) 0.005(4) 0.011(8) Uiso 1 1 d . . . . .
H3A H 0.327(4) 0.152(5) -0.054(4) 0.016(8) Uiso 1 1 d . . . . .
H3B H 0.196(4) 0.267(5) -0.054(4) 0.018(9) Uiso 1 1 d . . . . .
H4 H 0.215(4) 0.013(5) 0.074(4) 0.031(11) Uiso 1 1 d . . . . .
H5 H 0.364(4) 0.022(5) 0.331(4) 0.026(10) Uiso 1 1 d . . . . .
H5O H 0.516(5) 0.322(6) -0.031(4) 0.028(11) Uiso 1 1 d . . . . .
H6A H 0.466(4) 0.309(5) 0.385(4) 0.013(9) Uiso 1 1 d . . . . .
H6B H 0.593(4) 0.173(5) 0.429(4) 0.018(9) Uiso 1 1 d . . . . .
H6O H 0.589(5) 0.102(7) 0.148(5) 0.048(14) Uiso 1 1 d . . . . .
H8 H 0.702(3) 0.488(4) 0.238(3) 0.010(8) Uiso 1 1 d . . . . .
H10 H 0.718(4) 0.778(4) 0.303(4) 0.011(8) Uiso 1 1 d . . . . .
H10B H 0.627(4) 0.845(4) 0.390(4) 0.014(9) Uiso 1 1 d . . . . .
H11 H 0.521(3) 0.591(4) 0.380(3) 0.000(7) Uiso 1 1 d . . . . .
H12A H 0.221(5) 0.710(7) 0.230(5) 0.046(13) Uiso 1 1 d . . . . .
H12B H 0.099(5) 0.576(6) 0.220(4) 0.036(11) Uiso 1 1 d . . . . .
H12C H 0.091(5) 0.648(6) 0.070(5) 0.041(12) Uiso 1 1 d . . . . .
H13A H 0.916(4) 0.631(5) 0.330(4) 0.023(9) Uiso 1 1 d . . . . .
H13B H 1.022(5) 0.484(7) 0.432(5) 0.050(13) Uiso 1 1 d . . . . .
H13C H 1.060(4) 0.650(5) 0.504(4) 0.021(10) Uiso 1 1 d . . . . .
H14A H 0.922(4) 0.509(5) 0.747(4) 0.024(10) Uiso 1 1 d . . . . .
H14B H 1.068(5) 0.616(6) 0.754(5) 0.046(12) Uiso 1 1 d . . . . .
H14C H 1.043(5) 0.421(6) 0.714(4) 0.035(11) Uiso 1 1 d . . . . .


_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 O4 1.393(4) . ?
C1 O1 1.420(4) . ?
C1 C2 1.534(4) . ?
C1 H1 0.96(3) . ?
C2 O5 1.432(4) . ?
C2 C3 1.539(4) . ?
C2 C7 1.553(4) . ?
C3 C4 1.494(4) . ?
C3 H3A 1.00(4) . ?
C3 H3B 0.99(4) . ?
C4 C5 1.317(5) . ?
C4 H4 0.94(4) . ?
C5 C6 1.497(4) . ?
C5 H5 0.93(4) . ?
C6 C7 1.529(4) . ?
C6 H6A 0.92(4) . ?
C6 H6B 0.96(4) . ?
C7 O6 1.432(4) . ?
C7 C8 1.522(4) . ?
C8 O2 1.434(3) . ?
C8 C11 1.516(4) . ?
C8 H8 1.03(3) . ?
C9 O3 1.426(4) . ?
C9 O2 1.441(4) . ?
C9 C14 1.511(4) . ?
C9 C13 1.520(4) . ?
C10 O3 1.434(4) . ?
C10 C11 1.514(4) . ?
C10 H10 1.00(3) . ?
C10 H10B 0.94(4) . ?
C11 O1 1.431(4) . ?
C11 H11 0.98(3) . ?
C12 O4 1.423(4) . ?
C12 H12A 0.91(6) . ?
C12 H12B 0.96(4) . ?
C12 H12C 1.04(4) . ?
C13 H13A 1.09(4) . ?
C13 H13B 0.91(5) . ?
C13 H13C 0.92(4) . ?
C14 H14A 1.00(4) . ?
C14 H14B 1.08(5) . ?
C14 H14C 0.95(5) . ?
O5 H5O 0.87(5) . ?
O6 H6O 0.94(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
O4 C1 O1 112.2(2) . . ?
O4 C1 C2 108.6(2) . . ?
O1 C1 C2 111.6(2) . . ?
O4 C1 H1 109.1(18) . . ?
O1 C1 H1 100(2) . . ?
C2 C1 H1 115(2) . . ?
O5 C2 C1 102.3(2) . . ?
O5 C2 C3 109.2(2) . . ?
C1 C2 C3 111.1(3) . . ?
O5 C2 C7 109.4(2) . . ?
C1 C2 C7 112.8(2) . . ?
C3 C2 C7 111.6(2) . . ?
C4 C3 C2 115.9(3) . . ?
C4 C3 H3A 105(2) . . ?
C2 C3 H3A 109(2) . . ?
C4 C3 H3B 110(2) . . ?
C2 C3 H3B 110(2) . . ?
H3A C3 H3B 106(3) . . ?
C5 C4 C3 124.3(3) . . ?
C5 C4 H4 122(2) . . ?
C3 C4 H4 114(2) . . ?
C4 C5 C6 122.7(3) . . ?
C4 C5 H5 119(2) . . ?
C6 C5 H5 118(2) . . ?
C5 C6 C7 112.2(2) . . ?
C5 C6 H6A 108(2) . . ?
C7 C6 H6A 109(2) . . ?
C5 C6 H6B 108(2) . . ?
C7 C6 H6B 108(2) . . ?
H6A C6 H6B 112(3) . . ?
O6 C7 C8 105.6(2) . . ?
O6 C7 C6 110.0(3) . . ?
C8 C7 C6 112.6(2) . . ?
O6 C7 C2 108.3(2) . . ?
C8 C7 C2 107.2(2) . . ?
C6 C7 C2 112.8(2) . . ?
O2 C8 C11 107.0(2) . . ?
O2 C8 C7 110.7(2) . . ?
C11 C8 C7 113.1(2) . . ?
O2 C8 H8 113.1(17) . . ?
C11 C8 H8 106.8(19) . . ?
C7 C8 H8 106.2(19) . . ?
O3 C9 O2 109.8(2) . . ?
O3 C9 C14 104.8(3) . . ?
O2 C9 C14 106.2(3) . . ?
O3 C9 C13 112.6(3) . . ?
O2 C9 C13 111.7(3) . . ?
C14 C9 C13 111.3(3) . . ?
O3 C10 C11 108.9(2) . . ?
O3 C10 H10 111.2(19) . . ?
C11 C10 H10 107.0(19) . . ?
O3 C10 H10B 109(2) . . ?
C11 C10 H10B 108(2) . . ?
H10 C10 H10B 113(3) . . ?
O1 C11 C10 108.8(2) . . ?
O1 C11 C8 111.0(2) . . ?
C10 C11 C8 108.2(2) . . ?
O1 C11 H11 107.6(17) . . ?
C10 C11 H11 109.2(18) . . ?
C8 C11 H11 112.0(19) . . ?
O4 C12 H12A 113(3) . . ?
O4 C12 H12B 109(3) . . ?
H12A C12 H12B 115(4) . . ?
O4 C12 H12C 108(2) . . ?
H12A C12 H12C 108(4) . . ?
H12B C12 H12C 104(3) . . ?
C9 C13 H13A 113.9(18) . . ?
C9 C13 H13B 115(3) . . ?
H13A C13 H13B 104(3) . . ?
C9 C13 H13C 107(2) . . ?
H13A C13 H13C 109(3) . . ?
H13B C13 H13C 108(4) . . ?
C9 C14 H14A 112(2) . . ?
C9 C14 H14B 113(2) . . ?
H14A C14 H14B 105(3) . . ?
C9 C14 H14C 116(2) . . ?
H14A C14 H14C 105(3) . . ?
H14B C14 H14C 104(3) . . ?
C1 O1 C11 111.9(2) . . ?
C8 O2 C9 112.2(2) . . ?
C9 O3 C10 114.9(2) . . ?
C1 O4 C12 113.4(3) . . ?
C2 O5 H5O 106(3) . . ?
C7 O6 H6O 112(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
O4 C1 C2 O5 172.6(2) . . . . ?
O1 C1 C2 O5 -63.3(3) . . . . ?
O4 C1 C2 C3 56.2(3) . . . . ?
O1 C1 C2 C3 -179.7(2) . . . . ?
O4 C1 C2 C7 -70.0(3) . . . . ?
O1 C1 C2 C7 54.2(3) . . . . ?
O5 C2 C3 C4 150.0(3) . . . . ?
C1 C2 C3 C4 -97.9(3) . . . . ?
C7 C2 C3 C4 28.9(4) . . . . ?
C2 C3 C4 C5 -4.8(5) . . . . ?
C3 C4 C5 C6 1.7(5) . . . . ?
C4 C5 C6 C7 -23.4(5) . . . . ?
C5 C6 C7 O6 -73.6(3) . . . . ?
C5 C6 C7 C8 168.9(3) . . . . ?
C5 C6 C7 C2 47.4(4) . . . . ?
O5 C2 C7 O6 -49.4(3) . . . . ?
C1 C2 C7 O6 -162.6(2) . . . . ?
C3 C2 C7 O6 71.5(3) . . . . ?
O5 C2 C7 C8 64.1(3) . . . . ?
C1 C2 C7 C8 -49.0(3) . . . . ?
C3 C2 C7 C8 -174.9(2) . . . . ?
O5 C2 C7 C6 -171.5(2) . . . . ?
C1 C2 C7 C6 75.4(3) . . . . ?
C3 C2 C7 C6 -50.5(3) . . . . ?
O6 C7 C8 O2 -73.6(3) . . . . ?
C6 C7 C8 O2 46.5(3) . . . . ?
C2 C7 C8 O2 171.0(2) . . . . ?
O6 C7 C8 C11 166.3(2) . . . . ?
C6 C7 C8 C11 -73.6(3) . . . . ?
C2 C7 C8 C11 51.0(3) . . . . ?
O3 C10 C11 O1 -177.4(2) . . . . ?
O3 C10 C11 C8 -56.7(3) . . . . ?
O2 C8 C11 O1 -179.9(2) . . . . ?
C7 C8 C11 O1 -57.7(3) . . . . ?
O2 C8 C11 C10 60.8(3) . . . . ?
C7 C8 C11 C10 -177.0(2) . . . . ?
O4 C1 O1 C11 63.3(3) . . . . ?
C2 C1 O1 C11 -58.8(3) . . . . ?
C10 C11 O1 C1 179.4(2) . . . . ?
C8 C11 O1 C1 60.4(3) . . . . ?
C11 C8 O2 C9 -62.7(3) . . . . ?
C7 C8 O2 C9 173.7(2) . . . . ?
O3 C9 O2 C8 58.6(3) . . . . ?
C14 C9 O2 C8 171.4(2) . . . . ?
C13 C9 O2 C8 -67.1(3) . . . . ?
O2 C9 O3 C10 -54.6(3) . . . . ?
C14 C9 O3 C10 -168.3(3) . . . . ?
C13 C9 O3 C10 70.6(3) . . . . ?
C11 C10 O3 C9 54.8(3) . . . . ?
O1 C1 O4 C12 65.4(3) . . . . ?
C2 C1 O4 C12 -170.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5O O1 0.87(5) 2.07(4) 2.882(3) 153(4) 2_645
O6 H6O O5 0.94(5) 1.92(5) 2.832(3) 162(4) 2_645
C3 H3A O5 1.00(4) 2.61(4) 3.338(4) 130(2) 2_645
C6 H6A O4 0.92(4) 2.50(3) 2.991(4) 114(2) .

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1000541'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 O4'
_chemical_formula_sum            'C14 H18 O4'
_chemical_formula_weight         250.28

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.326(3)
_cell_length_b                   10.119(3)
_cell_length_c                   14.590(4)
_cell_angle_alpha                90.631(13)
_cell_angle_beta                 106.543(16)
_cell_angle_gamma                91.530(11)
_cell_volume                     1177.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5374
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Rgiaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19933
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.456
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5385
_reflns_number_gt                4127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;




_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XP SHELXTL/PC, Siemens Analytical'






_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5385
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.10799(19) 0.32921(15) 0.21473(11) 0.0145(3) Uani 1 1 d . . . . .
C2 C 0.0570(2) 0.20178(15) 0.15590(11) 0.0174(3) Uani 1 1 d . . . . .
H2A H 0.1336 0.1307 0.1847 0.021 Uiso 1 1 calc R U . . .
H2B H -0.0584 0.1735 0.1547 0.021 Uiso 1 1 calc R U . . .
C3 C 0.0654(2) 0.22692(17) 0.05510(12) 0.0197(4) Uani 1 1 d . . . . .
H3 H 0.0088 0.1655 0.0061 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1468(2) 0.32925(17) 0.03076(11) 0.0201(4) Uani 1 1 d . . . . .
H4 H 0.1429 0.3371 -0.0347 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2453(2) 0.43402(16) 0.10058(11) 0.0181(4) Uani 1 1 d . . . . .
H5A H 0.1828 0.5170 0.0923 0.022 Uiso 1 1 calc R U . . .
H5B H 0.3546 0.4524 0.0881 0.022 Uiso 1 1 calc R U . . .
C6 C 0.27362(19) 0.38582(15) 0.20204(11) 0.0150(3) Uani 1 1 d . . . . .
C7 C 0.3319(2) 0.47769(16) 0.28973(11) 0.0156(3) Uani 1 1 d . . . . .
H7A H 0.2704 0.5612 0.2801 0.019 Uiso 1 1 calc R U . . .
H7B H 0.4538 0.4982 0.3061 0.019 Uiso 1 1 calc R U . . .
C8 C 0.28777(19) 0.39341(16) 0.36658(11) 0.0158(3) Uani 1 1 d . . . . .
C9 C 0.2416(2) 0.46741(16) 0.44683(11) 0.0190(4) Uani 1 1 d . . . . .
H9A H 0.1904 0.4036 0.4821 0.023 Uiso 1 1 calc R U . . .
H9B H 0.3455 0.5048 0.4922 0.023 Uiso 1 1 calc R U . . .
C10 C 0.1218(2) 0.57782(17) 0.41268(11) 0.0192(4) Uani 1 1 d . . . . .
H10 H 0.1680 0.6654 0.4243 0.023 Uiso 1 1 calc R U . . .
C11 C -0.0415(2) 0.56584(16) 0.36805(11) 0.0191(4) Uani 1 1 d . . . . .
H11 H -0.0998 0.6458 0.3530 0.023 Uiso 1 1 calc R U . . .
C12 C -0.1436(2) 0.43964(16) 0.33891(11) 0.0187(4) Uani 1 1 d . . . . .
H12A H -0.2543 0.4506 0.3502 0.022 Uiso 1 1 calc R U . . .
H12B H -0.0871 0.3681 0.3806 0.022 Uiso 1 1 calc R U . . .
C13 C -0.1711(2) 0.39680(16) 0.23517(11) 0.0170(3) Uani 1 1 d . . . . .
C14 C -0.03660(19) 0.42836(16) 0.18656(11) 0.0163(3) Uani 1 1 d . . . . .
H14A H 0.0092 0.5192 0.2050 0.020 Uiso 1 1 calc R U . . .
H14B H -0.0868 0.4249 0.1163 0.020 Uiso 1 1 calc R U . . .
C15 C 0.59400(19) 0.82501(15) 0.21586(10) 0.0143(3) Uani 1 1 d . . . . .
C16 C 0.5833(2) 0.70213(16) 0.15358(11) 0.0173(3) Uani 1 1 d . . . . .
H16A H 0.6973 0.6754 0.1546 0.021 Uiso 1 1 calc R U . . .
H16B H 0.5280 0.6284 0.1783 0.021 Uiso 1 1 calc R U . . .
C17 C 0.4832(2) 0.73232(17) 0.05233(12) 0.0203(4) Uani 1 1 d . . . . .
H17 H 0.4896 0.6731 0.0026 0.024 Uiso 1 1 calc R U . . .
C18 C 0.3871(2) 0.83616(17) 0.02857(11) 0.0200(4) Uani 1 1 d . . . . .
H18 H 0.3315 0.8476 -0.0373 0.024 Uiso 1 1 calc R U . . .
C19 C 0.3600(2) 0.93765(16) 0.09913(11) 0.0180(3) Uani 1 1 d . . . . .
H19A H 0.2400 0.9589 0.0832 0.022 Uiso 1 1 calc R U . . .
H19B H 0.4255 1.0200 0.0966 0.022 Uiso 1 1 calc R U . . .
C20 C 0.41738(19) 0.87949(16) 0.19897(11) 0.0153(3) Uani 1 1 d . . . . .
C21 C 0.4429(2) 0.96512(16) 0.28903(11) 0.0162(3) Uani 1 1 d . . . . .
H21A H 0.3350 0.9804 0.3027 0.019 Uiso 1 1 calc R U . . .
H21B H 0.4974 1.0515 0.2830 0.019 Uiso 1 1 calc R U . . .
C22 C 0.55821(19) 0.88148(16) 0.36736(11) 0.0156(3) Uani 1 1 d . . . . .
C23 C 0.6910(2) 0.95716(16) 0.44719(11) 0.0181(4) Uani 1 1 d . . . . .
H23A H 0.6354 0.9920 0.4936 0.022 Uiso 1 1 calc R U . . .
H23B H 0.7744 0.8934 0.4813 0.022 Uiso 1 1 calc R U . . .
C24 C 0.7836(2) 1.07031(17) 0.41641(11) 0.0189(4) Uani 1 1 d . . . . .
H24 H 0.7504 1.1567 0.4275 0.023 Uiso 1 1 calc R U . . .
C25 C 0.9073(2) 1.06239(17) 0.37521(11) 0.0191(4) Uani 1 1 d . . . . .
H25 H 0.9573 1.1432 0.3629 0.023 Uiso 1 1 calc R U . . .
C26 C 0.9739(2) 0.93755(16) 0.34671(11) 0.0186(4) Uani 1 1 d . . . . .
H26A H 0.9527 0.8654 0.3874 0.022 Uiso 1 1 calc R U . . .
H26B H 1.0968 0.9489 0.3595 0.022 Uiso 1 1 calc R U . . .
C27 C 0.8987(2) 0.89601(16) 0.24242(11) 0.0170(3) Uani 1 1 d . . . . .
C28 C 0.71862(19) 0.92756(16) 0.19273(11) 0.0161(3) Uani 1 1 d . . . . .
H28A H 0.7016 0.9283 0.1228 0.019 Uiso 1 1 calc R U . . .
H28B H 0.6953 1.0169 0.2132 0.019 Uiso 1 1 calc R U . . .
O1 O 0.14822(13) 0.30764(10) 0.31610(7) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.38452(15) 0.27541(11) 0.21748(8) 0.0186(3) Uani 1 1 d . . . . .
O3 O 0.42207(14) 0.31042(12) 0.41221(8) 0.0197(3) Uani 1 1 d . . . . .
O4 O -0.29933(14) 0.33556(12) 0.19157(8) 0.0249(3) Uani 1 1 d . . . . .
O5 O 0.64586(13) 0.79738(10) 0.31687(7) 0.0149(2) Uani 1 1 d . . . . .
O6 O 0.30978(15) 0.76806(11) 0.20211(8) 0.0181(3) Uani 1 1 d . . . . .
O7 O 0.45697(15) 0.80188(12) 0.40814(8) 0.0193(3) Uani 1 1 d . . . . .
O8 O 0.98049(15) 0.83539(12) 0.19929(9) 0.0260(3) Uani 1 1 d . . . . .
H2O H 0.473(3) 0.302(2) 0.2044(15) 0.042(7) Uiso 1 1 d . . . . .
H7O H 0.521(3) 0.763(2) 0.455(2) 0.066(8) Uiso 1 1 d . . . . .
H3O H 0.436(3) 0.267(2) 0.3662(18) 0.055(8) Uiso 1 1 d . . . . .
H6O H 0.218(3) 0.798(2) 0.2084(16) 0.052(7) Uiso 1 1 d . . . . .


_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 1.4409(18) . ?
C1 C2 1.523(2) . ?
C1 C6 1.539(2) . ?
C1 C14 1.555(2) . ?
C2 C3 1.516(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.329(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.513(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.519(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O2 1.4468(19) . ?
C6 C7 1.527(2) . ?
C7 C8 1.536(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O3 1.4274(19) . ?
C8 O1 1.4458(19) . ?
C8 C9 1.527(2) . ?
C9 C10 1.510(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.332(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.503(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.521(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O4 1.224(2) . ?
C13 C14 1.516(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O5 1.4455(18) . ?
C15 C16 1.517(2) . ?
C15 C20 1.539(2) . ?
C15 C28 1.555(2) . ?
C16 C17 1.514(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.326(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.512(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.528(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O6 1.4306(19) . ?
C20 C21 1.526(2) . ?
C21 C22 1.544(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O7 1.4047(18) . ?
C22 O5 1.4576(18) . ?
C22 C23 1.539(2) . ?
C23 C24 1.506(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.336(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.494(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.521(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 O8 1.2221(19) . ?
C27 C28 1.512(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
O2 H2O 0.85(2) . ?
O3 H3O 0.83(2) . ?
O6 H6O 0.86(3) . ?
O7 H7O 0.85(3) . ?

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 112.56(12) . . ?
O1 C1 C6 103.21(12) . . ?
C2 C1 C6 109.80(13) . . ?
O1 C1 C14 108.67(12) . . ?
C2 C1 C14 109.75(13) . . ?
C6 C1 C14 112.75(13) . . ?
C3 C2 C1 108.45(13) . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
C4 C3 C2 124.31(15) . . ?
C4 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
C3 C4 C5 124.18(15) . . ?
C3 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C4 C5 C6 109.37(13) . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
O2 C6 C5 109.39(13) . . ?
O2 C6 C7 107.51(12) . . ?
C5 C6 C7 122.79(13) . . ?
O2 C6 C1 104.97(12) . . ?
C5 C6 C1 109.83(13) . . ?
C7 C6 C1 100.78(12) . . ?
C6 C7 C8 101.39(13) . . ?
C6 C7 H7A 111.5 . . ?
C8 C7 H7A 111.5 . . ?
C6 C7 H7B 111.5 . . ?
C8 C7 H7B 111.5 . . ?
H7A C7 H7B 109.3 . . ?
O3 C8 O1 107.09(12) . . ?
O3 C8 C9 106.10(13) . . ?
O1 C8 C9 109.24(13) . . ?
O3 C8 C7 111.37(12) . . ?
O1 C8 C7 105.78(12) . . ?
C9 C8 C7 116.90(14) . . ?
C10 C9 C8 113.93(13) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 127.08(16) . . ?
C11 C10 H10 116.5 . . ?
C9 C10 H10 116.5 . . ?
C10 C11 C12 127.09(15) . . ?
C10 C11 H11 116.5 . . ?
C12 C11 H11 116.5 . . ?
C11 C12 C13 114.73(13) . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
O4 C13 C14 120.09(15) . . ?
O4 C13 C12 120.48(14) . . ?
C14 C13 C12 119.41(14) . . ?
C13 C14 C1 111.37(12) . . ?
C13 C14 H14A 109.4 . . ?
C1 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C1 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O5 C15 C16 112.80(12) . . ?
O5 C15 C20 103.83(12) . . ?
C16 C15 C20 109.06(13) . . ?
O5 C15 C28 109.64(12) . . ?
C16 C15 C28 109.15(13) . . ?
C20 C15 C28 112.33(12) . . ?
C17 C16 C15 108.78(13) . . ?
C17 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C18 C17 C16 124.21(15) . . ?
C18 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
C17 C18 C19 124.47(15) . . ?
C17 C18 H18 117.8 . . ?
C19 C18 H18 117.8 . . ?
C18 C19 C20 108.03(13) . . ?
C18 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
C18 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
O6 C20 C21 109.58(12) . . ?
O6 C20 C19 108.31(13) . . ?
C21 C20 C19 121.72(14) . . ?
O6 C20 C15 105.99(12) . . ?
C21 C20 C15 100.60(13) . . ?
C19 C20 C15 109.45(13) . . ?
C20 C21 C22 102.95(13) . . ?
C20 C21 H21A 111.2 . . ?
C22 C21 H21A 111.2 . . ?
C20 C21 H21B 111.2 . . ?
C22 C21 H21B 111.2 . . ?
H21A C21 H21B 109.1 . . ?
O7 C22 O5 109.19(12) . . ?
O7 C22 C23 109.39(12) . . ?
O5 C22 C23 107.79(12) . . ?
O7 C22 C21 108.31(13) . . ?
O5 C22 C21 105.07(12) . . ?
C23 C22 C21 116.85(13) . . ?
C24 C23 C22 116.43(13) . . ?
C24 C23 H23A 108.2 . . ?
C22 C23 H23A 108.2 . . ?
C24 C23 H23B 108.2 . . ?
C22 C23 H23B 108.2 . . ?
H23A C23 H23B 107.3 . . ?
C25 C24 C23 127.07(16) . . ?
C25 C24 H24 116.5 . . ?
C23 C24 H24 116.5 . . ?
C24 C25 C26 125.76(16) . . ?
C24 C25 H25 117.1 . . ?
C26 C25 H25 117.1 . . ?
C25 C26 C27 114.55(13) . . ?
C25 C26 H26A 108.6 . . ?
C27 C26 H26A 108.6 . . ?
C25 C26 H26B 108.6 . . ?
C27 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
O8 C27 C28 119.92(15) . . ?
O8 C27 C26 120.95(14) . . ?
C28 C27 C26 119.11(13) . . ?
C27 C28 C15 111.66(13) . . ?
C27 C28 H28A 109.3 . . ?
C15 C28 H28A 109.3 . . ?
C27 C28 H28B 109.3 . . ?
C15 C28 H28B 109.3 . . ?
H28A C28 H28B 108.0 . . ?
C1 O1 C8 110.10(11) . . ?
C6 O2 H2O 106.9(14) . . ?
C8 O3 H3O 102.1(16) . . ?
C15 O5 C22 110.03(11) . . ?
C20 O6 H6O 107.5(15) . . ?
C22 O7 H7O 107.8(18) . . ?

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 C3 -164.12(12) . . . . ?
C6 C1 C2 C3 -49.76(16) . . . . ?
C14 C1 C2 C3 74.71(15) . . . . ?
C1 C2 C3 C4 16.9(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 14.5(2) . . . . ?
C4 C5 C6 O2 67.33(16) . . . . ?
C4 C5 C6 C7 -165.35(14) . . . . ?
C4 C5 C6 C1 -47.38(17) . . . . ?
O1 C1 C6 O2 71.16(14) . . . . ?
C2 C1 C6 O2 -49.05(16) . . . . ?
C14 C1 C6 O2 -171.77(12) . . . . ?
O1 C1 C6 C5 -171.33(12) . . . . ?
C2 C1 C6 C5 68.45(16) . . . . ?
C14 C1 C6 C5 -54.26(17) . . . . ?
O1 C1 C6 C7 -40.43(14) . . . . ?
C2 C1 C6 C7 -160.65(12) . . . . ?
C14 C1 C6 C7 76.64(15) . . . . ?
O2 C6 C7 C8 -68.75(14) . . . . ?
C5 C6 C7 C8 163.12(14) . . . . ?
C1 C6 C7 C8 40.87(14) . . . . ?
C6 C7 C8 O3 88.43(15) . . . . ?
C6 C7 C8 O1 -27.58(14) . . . . ?
C6 C7 C8 C9 -149.41(13) . . . . ?
O3 C8 C9 C10 169.94(13) . . . . ?
O1 C8 C9 C10 -74.93(17) . . . . ?
C7 C8 C9 C10 45.08(19) . . . . ?
C8 C9 C10 C11 73.8(2) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C10 C11 C12 C13 -97.4(2) . . . . ?
C11 C12 C13 O4 -148.97(15) . . . . ?
C11 C12 C13 C14 32.2(2) . . . . ?
O4 C13 C14 C1 -99.28(17) . . . . ?
C12 C13 C14 C1 79.58(18) . . . . ?
O1 C1 C14 C13 -43.15(17) . . . . ?
C2 C1 C14 C13 80.33(16) . . . . ?
C6 C1 C14 C13 -156.93(13) . . . . ?
O5 C15 C16 C17 164.09(12) . . . . ?
C20 C15 C16 C17 49.28(16) . . . . ?
C28 C15 C16 C17 -73.78(16) . . . . ?
C15 C16 C17 C18 -15.5(2) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C17 C18 C19 C20 -16.1(2) . . . . ?
C18 C19 C20 O6 -65.06(16) . . . . ?
C18 C19 C20 C21 166.66(14) . . . . ?
C18 C19 C20 C15 50.07(17) . . . . ?
O5 C15 C20 O6 -74.15(14) . . . . ?
C16 C15 C20 O6 46.34(15) . . . . ?
C28 C15 C20 O6 167.47(12) . . . . ?
O5 C15 C20 C21 39.95(14) . . . . ?
C16 C15 C20 C21 160.43(12) . . . . ?
C28 C15 C20 C21 -78.43(15) . . . . ?
O5 C15 C20 C19 169.25(12) . . . . ?
C16 C15 C20 C19 -70.27(16) . . . . ?
C28 C15 C20 C19 50.87(17) . . . . ?
O6 C20 C21 C22 72.36(15) . . . . ?
C19 C20 C21 C22 -159.91(14) . . . . ?
C15 C20 C21 C22 -38.99(14) . . . . ?
C20 C21 C22 O7 -91.84(14) . . . . ?
C20 C21 C22 O5 24.75(15) . . . . ?
C20 C21 C22 C23 144.15(13) . . . . ?
O7 C22 C23 C24 -166.01(13) . . . . ?
O5 C22 C23 C24 75.38(16) . . . . ?
C21 C22 C23 C24 -42.55(19) . . . . ?
C22 C23 C24 C25 -76.7(2) . . . . ?
C23 C24 C25 C26 3.2(3) . . . . ?
C24 C25 C26 C27 96.0(2) . . . . ?
C25 C26 C27 O8 149.24(15) . . . . ?
C25 C26 C27 C28 -32.3(2) . . . . ?
O8 C27 C28 C15 97.01(17) . . . . ?
C26 C27 C28 C15 -81.42(18) . . . . ?
O5 C15 C28 C27 43.85(16) . . . . ?
C16 C15 C28 C27 -80.16(16) . . . . ?
C20 C15 C28 C27 158.75(13) . . . . ?
C2 C1 O1 C8 142.41(13) . . . . ?
C6 C1 O1 C8 24.10(15) . . . . ?
C14 C1 O1 C8 -95.80(14) . . . . ?
O3 C8 O1 C1 -116.71(13) . . . . ?
C9 C8 O1 C1 128.80(13) . . . . ?
C7 C8 O1 C1 2.17(15) . . . . ?
C16 C15 O5 C22 -143.62(13) . . . . ?
C20 C15 O5 C22 -25.69(15) . . . . ?
C28 C15 O5 C22 94.53(14) . . . . ?
O7 C22 O5 C15 116.64(13) . . . . ?
C23 C22 O5 C15 -124.62(13) . . . . ?
C21 C22 O5 C15 0.66(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O4 0.85(2) 1.98(2) 2.8156(19) 169(2) 1_655
O7 H7O O3 0.85(3) 2.01(3) 2.7926(18) 153(3) 2_666
O3 H3O O2 0.83(2) 2.09(2) 2.7859(19) 141(2) .
O6 H6O O8 0.86(3) 1.99(3) 2.8316(19) 167(2) 1_455

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 998373'
