# Electronic Supplementary Material (ESI) for Chemical Communications
# 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. 
#
####################################################################### 

data_I
_database_code_depnum_ccdc_archive 'CCDC 916330'
#TrackingRef 'Diol.cif'
_chemical_name_systematic        ?
_chemical_name_common            SVG447
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         292.32
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   7.3105(2)
_cell_length_b                   12.5653(3)
_cell_length_c                   16.0454(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.0430(10)
_cell_angle_gamma                90
_cell_volume                     1441.47(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5914
_cell_measurement_theta_min      2.5959
_cell_measurement_theta_max      26.4535
_cell_measurement_temperature    296.(2)
_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.98
_exptl_special_details           
;
;
_diffrn_ambient_temperature      296.(2)
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19484
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_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.
;
_reflns_number_total             2636
_reflns_number_gt                2018
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1548
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_number_reflns         2636
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0917P)^2^+0.2429P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
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'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.1733(5) 0.6227(3) 0.4562(2) 0.1019(12) Uani d . 1 . .
H H1A 1.1583 0.5594 0.4219 0.153 Uiso calc R 1 . .
H H1B 1.1477 0.6068 0.5111 0.153 Uiso calc R 1 . .
H H1C 1.2994 0.6482 0.4629 0.153 Uiso calc R 1 . .
C C2 1.0759(3) 0.74358(14) 0.33953(12) 0.0408(5) Uani d . 1 . .
C C3 1.1914(3) 0.69445(16) 0.29298(14) 0.0499(5) Uani d . 1 . .
H H3 1.2511 0.6311 0.3125 0.06 Uiso calc R 1 . .
C C4 1.2185(3) 0.73885(17) 0.21780(14) 0.0542(6) Uani d . 1 . .
H H4 1.2972 0.7055 0.1872 0.065 Uiso calc R 1 . .
C C5 1.1300(3) 0.83213(17) 0.18773(13) 0.0497(5) Uani d . 1 . .
C C6 1.0081(3) 0.88315(14) 0.23345(11) 0.0402(5) Uani d . 1 . .
C C7 0.9823(2) 0.83840(13) 0.31124(11) 0.0349(4) Uani d . 1 . .
C C8 1.2590(5) 0.8282(2) 0.06305(19) 0.0941(10) Uani d . 1 . .
H H8A 1.3836 0.8167 0.0952 0.141 Uiso calc R 1 . .
H H8B 1.2636 0.8714 0.0142 0.141 Uiso calc R 1 . .
H H8C 1.2023 0.761 0.0447 0.141 Uiso calc R 1 . .
C C9 0.9059(3) 0.98146(16) 0.20011(12) 0.0457(5) Uani d . 1 . .
C C10 0.7608(3) 1.02210(17) 0.24558(12) 0.0468(5) Uani d . 1 . .
H H10A 0.6447 0.9841 0.2251 0.056 Uiso calc R 1 . .
H H10B 0.7384 1.0968 0.2321 0.056 Uiso calc R 1 . .
C C11 0.8523(2) 0.89022(13) 0.36338(10) 0.0321(4) Uani d . 1 . .
C C12 0.6678(3) 0.82807(15) 0.35119(12) 0.0412(5) Uani d . 1 . .
H H12A 0.6108 0.8251 0.2909 0.049 Uiso calc R 1 . .
H H12B 0.6936 0.7557 0.3712 0.049 Uiso calc R 1 . .
C C13 0.5306(3) 0.87906(16) 0.39929(14) 0.0503(5) Uani d . 1 . .
H H13A 0.4148 0.8389 0.3885 0.06 Uiso calc R 1 . .
H H13B 0.5829 0.8766 0.46 0.06 Uiso calc R 1 . .
C C14 0.4899(3) 0.99379(17) 0.37205(14) 0.0522(5) Uani d . 1 . .
H H14A 0.4057 1.025 0.4047 0.063 Uiso calc R 1 . .
H H14B 0.4295 0.9963 0.3122 0.063 Uiso calc R 1 . .
C C15 0.6712(3) 1.05695(15) 0.38658(13) 0.0433(5) Uani d . 1 . .
H H15A 0.7234 1.0603 0.4473 0.052 Uiso calc R 1 . .
H H15B 0.6438 1.1292 0.3664 0.052 Uiso calc R 1 . .
C C16 0.8171(2) 1.00941(13) 0.34153(11) 0.0358(4) Uani d . 1 . .
O O6 0.98887(17) 1.06694(10) 0.36558(8) 0.0429(4) Uani d . 1 . .
H H6 1.0344 1.0559 0.416 0.064 Uiso calc R 1 . .
O O1 1.0482(2) 0.70134(11) 0.41602(9) 0.0525(4) Uani d . 1 . .
O O2 1.1531(3) 0.88015(14) 0.11421(11) 0.0791(6) Uani d . 1 . .
O O3 0.9346(3) 1.03013(15) 0.13863(11) 0.0870(6) Uani d . 1 . .
O O4 0.94040(18) 0.89120(10) 0.45253(7) 0.0412(4) Uani d . 1 . .
H H4A 0.9843 0.8322 0.4666 0.062 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.108(3) 0.096(2) 0.112(2) 0.0543(19) 0.045(2) 0.0546(19)
C2 0.0367(10) 0.0373(10) 0.0486(11) -0.0042(8) 0.0095(8) -0.0070(8)
C3 0.0397(11) 0.0426(11) 0.0667(13) 0.0030(9) 0.0098(10) -0.0147(10)
C4 0.0445(12) 0.0557(13) 0.0676(14) -0.0043(10) 0.0239(10) -0.0262(11)
C5 0.0519(12) 0.0525(12) 0.0500(11) -0.0108(10) 0.0224(9) -0.0163(9)
C6 0.0390(10) 0.0431(11) 0.0407(10) -0.0101(8) 0.0132(8) -0.0108(8)
C7 0.0293(9) 0.0348(9) 0.0406(10) -0.0054(7) 0.0076(7) -0.0088(7)
C8 0.131(3) 0.088(2) 0.0851(19) -0.0076(19) 0.073(2) -0.0255(16)
C9 0.0537(12) 0.0479(11) 0.0369(10) -0.0054(9) 0.0127(8) -0.0015(8)
C10 0.0468(11) 0.0488(11) 0.0447(11) 0.0060(9) 0.0095(8) 0.0069(9)
C11 0.0310(9) 0.0338(9) 0.0313(9) -0.0034(7) 0.0060(7) -0.0038(7)
C12 0.0366(10) 0.0432(10) 0.0455(10) -0.0103(8) 0.0122(8) -0.0084(8)
C13 0.0368(11) 0.0565(13) 0.0623(12) -0.0134(9) 0.0210(9) -0.0120(10)
C14 0.0357(11) 0.0641(13) 0.0586(13) 0.0055(9) 0.0139(9) -0.0087(10)
C15 0.0416(11) 0.0399(10) 0.0495(11) 0.0062(8) 0.0123(8) -0.0033(8)
C16 0.0329(9) 0.0351(9) 0.0399(10) -0.0014(7) 0.0088(7) -0.0021(7)
O6 0.0415(8) 0.0377(7) 0.0507(8) -0.0095(6) 0.0124(6) -0.0035(6)
O1 0.0582(9) 0.0417(8) 0.0595(9) 0.0116(6) 0.0168(7) 0.0082(6)
O2 0.1104(15) 0.0747(11) 0.0707(11) 0.0032(10) 0.0616(11) -0.0063(8)
O3 0.1204(16) 0.0836(12) 0.0714(12) 0.0249(11) 0.0531(11) 0.0299(10)
O4 0.0488(8) 0.0376(7) 0.0344(7) 0.0022(6) 0.0024(5) -0.0026(5)
_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.409(3) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C2 C3 . 1.384(3) ?
C2 O1 . 1.390(2) ?
C2 C7 . 1.402(3) ?
C3 C4 . 1.380(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.376(3) ?
C4 H4 . 0.93 ?
C5 O2 . 1.366(3) ?
C5 C6 . 1.420(3) ?
C6 C7 . 1.417(3) ?
C6 C9 . 1.484(3) ?
C7 C11 . 1.535(2) ?
C8 O2 . 1.402(3) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 O3 . 1.216(2) ?
C9 C10 . 1.497(3) ?
C10 C16 . 1.517(3) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 O4 . 1.441(2) ?
C11 C12 . 1.536(2) ?
C11 C16 . 1.547(2) ?
C12 C13 . 1.528(3) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C14 . 1.518(3) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 C15 . 1.520(3) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.529(2) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 O6 . 1.431(2) ?
O6 H6 . 0.82 ?
O4 H4A . 0.82 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 O1 . . 121.60(17) ?
C3 C2 C7 . . 121.07(18) ?
O1 C2 C7 . . 117.33(15) ?
C4 C3 C2 . . 120.42(19) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C5 C4 C3 . . 120.53(18) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
O2 C5 C4 . . 123.04(18) ?
O2 C5 C6 . . 116.78(19) ?
C4 C5 C6 . . 120.19(19) ?
C7 C6 C5 . . 119.29(18) ?
C7 C6 C9 . . 119.88(16) ?
C5 C6 C9 . . 120.83(17) ?
C2 C7 C6 . . 118.47(16) ?
C2 C7 C11 . . 119.99(15) ?
C6 C7 C11 . . 121.53(16) ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 C6 . . 123.50(19) ?
O3 C9 C10 . . 118.93(19) ?
C6 C9 C10 . . 117.57(16) ?
C9 C10 C16 . . 112.91(16) ?
C9 C10 H10A . . 109.0 ?
C16 C10 H10A . . 109.0 ?
C9 C10 H10B . . 109.0 ?
C16 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
O4 C11 C7 . . 110.21(13) ?
O4 C11 C12 . . 109.24(13) ?
C7 C11 C12 . . 109.99(13) ?
O4 C11 C16 . . 103.62(13) ?
C7 C11 C16 . . 112.31(14) ?
C12 C11 C16 . . 111.28(14) ?
C13 C12 C11 . . 111.97(15) ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12B . . 109.2 ?
C11 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C14 C13 C12 . . 111.27(17) ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13B . . 109.4 ?
C12 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C13 C14 C15 . . 109.84(16) ?
C13 C14 H14A . . 109.7 ?
C15 C14 H14A . . 109.7 ?
C13 C14 H14B . . 109.7 ?
C15 C14 H14B . . 109.7 ?
H14A C14 H14B . . 108.2 ?
C14 C15 C16 . . 113.28(15) ?
C14 C15 H15A . . 108.9 ?
C16 C15 H15A . . 108.9 ?
C14 C15 H15B . . 108.9 ?
C16 C15 H15B . . 108.9 ?
H15A C15 H15B . . 107.7 ?
O6 C16 C10 . . 104.92(14) ?
O6 C16 C15 . . 109.55(14) ?
C10 C16 C15 . . 111.75(15) ?
O6 C16 C11 . . 109.43(14) ?
C10 C16 C11 . . 109.20(14) ?
C15 C16 C11 . . 111.76(14) ?
C16 O6 H6 . . 109.5 ?
C2 O1 C1 . . 118.13(18) ?
C5 O2 C8 . . 118.9(2) ?
C11 O4 H4A . . 109.5 ?


data_II
_database_code_depnum_ccdc_archive 'CCDC 916331'
#TrackingRef 'Triol-acetate.cif'
_chemical_name_systematic        ?
_chemical_name_common            SVG491-1
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         352.37
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   19.4252(3)
_cell_length_b                   10.82670(10)
_cell_length_c                   18.5071(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.9380(10)
_cell_angle_gamma                90
_cell_volume                     3469.92(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      2.2650
_cell_measurement_theta_max      27.8659
_cell_measurement_temperature    296.(2)
_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98
_exptl_special_details           
;
;
_diffrn_ambient_temperature      296.(2)
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            30199
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_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.
;
_reflns_number_total             3178
_reflns_number_gt                2599
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1298
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_number_reflns         3178
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+2.5352P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.381
_refine_ls_shift/su_mean         0.007
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
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'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.33237(10) 0.13672(17) 0.47874(10) 0.0397(4) Uani d . 1 . .
C C2 0.29099(11) 0.08474(18) 0.51486(11) 0.0470(5) Uani d . 1 . .
H H2 0.3164 0.0607 0.5689 0.056 Uiso calc R 1 . .
C C3 0.21186(11) 0.06780(18) 0.47148(11) 0.0470(5) Uani d . 1 . .
H H3A 0.1844 0.031 0.4959 0.056 Uiso calc R 1 . .
C C4 0.17409(10) 0.10603(16) 0.39178(10) 0.0399(4) Uani d . 1 . .
C C5 0.21526(9) 0.16234(14) 0.35469(9) 0.0338(4) Uani d . 1 . .
C C6 0.29534(9) 0.17658(14) 0.39749(9) 0.0331(4) Uani d . 1 . .
C C7 0.45193(12) 0.1213(2) 0.60343(11) 0.0578(5) Uani d . 1 . .
H H7A 0.4313 0.1689 0.6329 0.087 Uiso calc R 1 . .
H H7B 0.5059 0.1393 0.6236 0.087 Uiso calc R 1 . .
H H7C 0.4453 0.035 0.6102 0.087 Uiso calc R 1 . .
C C8 0.05159(14) 0.0324(3) 0.37564(16) 0.0711(7) Uani d . 1 . .
H H8A 0.0705 -0.0503 0.3909 0.107 Uiso calc R 1 . .
H H8B -0.0015 0.0297 0.3354 0.107 Uiso calc R 1 . .
H H8C 0.0555 0.0763 0.4224 0.107 Uiso calc R 1 . .
C C9 0.34300(9) 0.22529(15) 0.35640(9) 0.0337(4) Uani d . 1 . .
C C10 0.38194(10) 0.11459(16) 0.33698(10) 0.0389(4) Uani d . 1 . .
H H10A 0.418 0.0765 0.3875 0.047 Uiso calc R 1 . .
H H10B 0.3427 0.0538 0.3067 0.047 Uiso calc R 1 . .
C C11 0.42491(12) 0.1490(2) 0.28839(12) 0.0542(5) Uani d . 1 . .
H H11A 0.4694 0.1994 0.3217 0.065 Uiso calc R 1 . .
H H11B 0.4435 0.0744 0.2739 0.065 Uiso calc R 1 . .
C C12 0.37324(12) 0.2196(2) 0.21169(12) 0.0570(5) Uani d . 1 . .
H H12A 0.403 0.2452 0.1841 0.068 Uiso calc R 1 . .
H H12B 0.3318 0.1663 0.1755 0.068 Uiso calc R 1 . .
C C13 0.33929(11) 0.33264(18) 0.23269(12) 0.0491(5) Uani d . 1 . .
H H13A 0.3058 0.3754 0.183 0.059 Uiso calc R 1 . .
H H13B 0.3809 0.3884 0.2653 0.059 Uiso calc R 1 . .
C C14 0.29316(9) 0.30112(14) 0.27898(10) 0.0355(4) Uani d . 1 . .
C C15 0.22062(9) 0.22716(15) 0.22786(9) 0.0328(4) Uani d . 1 . .
H H15 0.2358 0.1455 0.2172 0.039 Uiso calc R 1 . .
C C16 0.16898(9) 0.21068(15) 0.26889(10) 0.0365(4) Uani d . 1 . .
H H16 0.1303 0.148 0.2383 0.044 Uiso calc R 1 . .
C C17 0.14248(11) 0.22380(17) 0.08462(10) 0.0429(4) Uani d . 1 . .
C C18 0.10323(14) 0.3028(2) 0.01143(12) 0.0617(6) Uani d . 1 . .
H H18A 0.1373 0.3167 -0.0124 0.093 Uiso calc R 1 . .
H H18B 0.0898 0.3806 0.0266 0.093 Uiso calc R 1 . .
H H18C 0.0573 0.2623 -0.0271 0.093 Uiso calc R 1 . .
O O1 0.41197(7) 0.15251(14) 0.51913(7) 0.0524(4) Uani d . 1 . .
O O2 0.09619(7) 0.09364(13) 0.34343(8) 0.0533(4) Uani d . 1 . .
O O3 0.12868(8) 0.32121(14) 0.26776(9) 0.0546(4) Uani d . 1 . .
H H3 0.1594 0.3786 0.2853 0.082 Uiso calc R 1 . .
O O4 0.40016(7) 0.31316(12) 0.40620(8) 0.0480(3) Uani d . 1 . .
H H4 0.4199 0.2898 0.4535 0.072 Uiso calc R 1 . .
O O5 0.26910(7) 0.41349(11) 0.30219(7) 0.0464(3) Uani d . 1 . .
H H5 0.3054 0.4426 0.3422 0.07 Uiso calc R 1 . .
O O6 0.17812(7) 0.29102(10) 0.15128(6) 0.0400(3) Uani d . 1 . .
O O7 0.14139(12) 0.11287(14) 0.08439(9) 0.0849(6) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0419(9) 0.0428(9) 0.0286(8) 0.0093(7) 0.0108(7) 0.0013(7)
C2 0.0575(11) 0.0523(11) 0.0301(8) 0.0114(9) 0.0190(8) 0.0081(8)
C3 0.0584(12) 0.0473(10) 0.0435(10) 0.0051(9) 0.0304(9) 0.0068(8)
C4 0.0420(9) 0.0383(9) 0.0406(9) 0.0033(7) 0.0198(8) -0.0005(7)
C5 0.0382(9) 0.0304(8) 0.0306(8) 0.0033(7) 0.0136(7) -0.0005(6)
C6 0.0387(9) 0.0297(8) 0.0280(8) 0.0055(7) 0.0126(7) -0.0007(6)
C7 0.0544(12) 0.0722(14) 0.0304(9) 0.0172(10) 0.0048(8) 0.0049(9)
C8 0.0591(13) 0.0822(17) 0.0791(16) -0.0144(12) 0.0375(12) 0.0066(13)
C9 0.0314(8) 0.0329(8) 0.0289(8) -0.0022(6) 0.0068(6) -0.0010(6)
C10 0.0365(9) 0.0421(9) 0.0353(9) 0.0073(7) 0.0138(7) 0.0051(7)
C11 0.0462(10) 0.0704(13) 0.0511(11) 0.0100(10) 0.0266(9) 0.0099(10)
C12 0.0520(11) 0.0796(15) 0.0481(11) 0.0068(10) 0.0303(9) 0.0145(10)
C13 0.0456(10) 0.0507(11) 0.0448(10) -0.0065(8) 0.0152(8) 0.0142(8)
C14 0.0377(9) 0.0283(8) 0.0339(9) 0.0008(7) 0.0105(7) 0.0019(6)
C15 0.0368(8) 0.0295(8) 0.0246(8) 0.0025(6) 0.0074(6) 0.0028(6)
C16 0.0335(8) 0.0371(9) 0.0319(8) -0.0005(7) 0.0085(7) 0.0000(7)
C17 0.0504(10) 0.0417(10) 0.0294(9) 0.0025(8) 0.0117(8) -0.0004(7)
C18 0.0704(14) 0.0632(13) 0.0339(10) 0.0026(11) 0.0082(9) 0.0080(9)
O1 0.0418(7) 0.0743(9) 0.0291(6) 0.0075(6) 0.0056(5) 0.0076(6)
O2 0.0404(7) 0.0647(9) 0.0543(8) -0.0050(6) 0.0211(6) 0.0077(7)
O3 0.0495(8) 0.0611(8) 0.0522(8) 0.0200(6) 0.0221(7) 0.0120(7)
O4 0.0422(7) 0.0453(7) 0.0396(7) -0.0100(6) 0.0038(6) -0.0027(6)
O5 0.0492(7) 0.0290(6) 0.0429(7) 0.0014(5) 0.0051(6) -0.0048(5)
O6 0.0480(7) 0.0342(6) 0.0263(6) 0.0017(5) 0.0066(5) 0.0038(5)
O7 0.1305(16) 0.0431(9) 0.0387(8) 0.0050(9) 0.0012(9) -0.0046(6)
_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.377(3) ?
C1 O1 . 1.390(2) ?
C1 C6 . 1.409(2) ?
C2 C3 . 1.387(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.380(3) ?
C3 H3A . 0.93 ?
C4 O2 . 1.372(2) ?
C4 C5 . 1.407(2) ?
C5 C6 . 1.398(2) ?
C5 C16 . 1.520(2) ?
C6 C9 . 1.533(2) ?
C7 O1 . 1.433(2) ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 O2 . 1.419(2) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 O4 . 1.4355(19) ?
C9 C10 . 1.544(2) ?
C9 C14 . 1.552(2) ?
C10 C11 . 1.524(3) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 C12 . 1.522(3) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 C13 . 1.522(3) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C14 . 1.533(3) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 O5 . 1.437(2) ?
C14 C15 . 1.521(2) ?
C15 O6 . 1.4520(18) ?
C15 C16 . 1.518(2) ?
C15 H15 . 0.98 ?
C16 O3 . 1.425(2) ?
C16 H16 . 0.98 ?
C17 O7 . 1.201(2) ?
C17 O6 . 1.326(2) ?
C17 C18 . 1.488(3) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
O3 H3 . 0.82 ?
O4 H4 . 0.82 ?
O5 H5 . 0.82 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 O1 . . 122.75(15) ?
C2 C1 C6 . . 121.01(16) ?
O1 C1 C6 . . 116.24(15) ?
C1 C2 C3 . . 120.71(16) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C4 C3 C2 . . 119.49(17) ?
C4 C3 H3A . . 120.3 ?
C2 C3 H3A . . 120.3 ?
O2 C4 C3 . . 124.27(16) ?
O2 C4 C5 . . 115.27(15) ?
C3 C4 C5 . . 120.46(16) ?
C6 C5 C4 . . 120.25(14) ?
C6 C5 C16 . . 122.25(14) ?
C4 C5 C16 . . 117.45(14) ?
C5 C6 C1 . . 118.04(15) ?
C5 C6 C9 . . 121.58(13) ?
C1 C6 C9 . . 120.24(14) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O4 C9 C6 . . 112.01(13) ?
O4 C9 C10 . . 110.23(13) ?
C6 C9 C10 . . 108.54(13) ?
O4 C9 C14 . . 102.70(12) ?
C6 C9 C14 . . 112.06(13) ?
C10 C9 C14 . . 111.24(13) ?
C11 C10 C9 . . 113.86(15) ?
C11 C10 H10A . . 108.8 ?
C9 C10 H10A . . 108.8 ?
C11 C10 H10B . . 108.8 ?
C9 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
C12 C11 C10 . . 111.53(15) ?
C12 C11 H11A . . 109.3 ?
C10 C11 H11A . . 109.3 ?
C12 C11 H11B . . 109.3 ?
C10 C11 H11B . . 109.3 ?
H11A C11 H11B . . 108.0 ?
C13 C12 C11 . . 110.16(17) ?
C13 C12 H12A . . 109.6 ?
C11 C12 H12A . . 109.6 ?
C13 C12 H12B . . 109.6 ?
C11 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C12 C13 C14 . . 113.23(15) ?
C12 C13 H13A . . 108.9 ?
C14 C13 H13A . . 108.9 ?
C12 C13 H13B . . 108.9 ?
C14 C13 H13B . . 108.9 ?
H13A C13 H13B . . 107.7 ?
O5 C14 C15 . . 107.25(13) ?
O5 C14 C13 . . 109.29(14) ?
C15 C14 C13 . . 112.40(14) ?
O5 C14 C9 . . 108.86(13) ?
C15 C14 C9 . . 108.08(13) ?
C13 C14 C9 . . 110.84(14) ?
O6 C15 C14 . . 108.25(12) ?
O6 C15 C16 . . 109.39(12) ?
C14 C15 C16 . . 112.74(13) ?
O6 C15 H15 . . 108.8 ?
C14 C15 H15 . . 108.8 ?
C16 C15 H15 . . 108.8 ?
O3 C16 C15 . . 112.16(14) ?
O3 C16 C5 . . 111.44(13) ?
C15 C16 C5 . . 110.54(13) ?
O3 C16 H16 . . 107.5 ?
C15 C16 H16 . . 107.5 ?
C5 C16 H16 . . 107.5 ?
O7 C17 O6 . . 123.60(16) ?
O7 C17 C18 . . 124.82(17) ?
O6 C17 C18 . . 111.57(16) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C1 O1 C7 . . 118.59(15) ?
C4 O2 C8 . . 118.34(16) ?
C16 O3 H3 . . 109.5 ?
C9 O4 H4 . . 109.5 ?
C14 O5 H5 . . 109.5 ?
C17 O6 C15 . . 118.24(13) ?


data_III
_database_code_depnum_ccdc_archive 'CCDC 916332'
#TrackingRef 'Triol.cif'
_chemical_name_systematic        ?
_chemical_name_common            SVG453
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         308.32
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   11.5674(5)
_cell_length_b                   12.7922(6)
_cell_length_c                   10.8484(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.270(2)
_cell_angle_gamma                90
_cell_volume                     1451.65(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3602
_cell_measurement_theta_min      2.5152
_cell_measurement_theta_max      21.4984
_cell_measurement_temperature    296.(2)
_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98
_exptl_special_details           
;
;
_diffrn_ambient_temperature      296.(2)
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            24773
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_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.
;
_reflns_number_total             2556
_reflns_number_gt                1690
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1616
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_number_reflns         2556
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
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'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.16617(17) 0.90358(12) 0.96121(15) 0.0473(5) Uani d . 1 . .
H H1 0.1891 0.9505 1.0181 0.071 Uiso calc R 1 . .
O O2 0.20777(16) 0.76594(12) 0.79743(15) 0.0481(5) Uani d . 1 . .
H H2 0.2116 0.7512 0.8726 0.072 Uiso calc R 1 . .
O O6 0.27852(18) 1.08901(14) 1.03787(17) 0.0583(5) Uani d . 1 . .
O O3 0.08163(18) 0.79775(14) 0.50634(16) 0.0611(5) Uani d . 1 . .
H H3 0.1239 0.7441 0.5329 0.092 Uiso calc R 1 . .
O O5 0.46723(18) 1.02821(16) 0.6536(2) 0.0713(6) Uani d . 1 . .
C C1 0.0423(2) 1.02606(17) 0.7793(3) 0.0460(6) Uani d . 1 . .
H H1A 0.0621 1.081 0.8469 0.055 Uiso calc R 1 . .
H H1B 0.0394 1.0575 0.6966 0.055 Uiso calc R 1 . .
C C2 -0.0889(2) 0.9821(2) 0.7496(3) 0.0629(8) Uani d . 1 . .
H H2A -0.0902 0.9578 0.8337 0.075 Uiso calc R 1 . .
H H2B -0.1526 1.0367 0.7122 0.075 Uiso calc R 1 . .
C C16 0.3254(3) 1.1724(2) 1.1340(3) 0.0689(8) Uani d . 1 . .
H H16A 0.4127 1.1588 1.1958 0.103 Uiso calc R 1 . .
H H16B 0.2746 1.1777 1.1842 0.103 Uiso calc R 1 . .
H H16C 0.3206 1.2368 1.0866 0.103 Uiso calc R 1 . .
C C4 -0.0195(2) 0.80886(19) 0.7043(2) 0.0485(6) Uani d . 1 . .
H H4A -0.0406 0.7532 0.6375 0.058 Uiso calc R 1 . .
H H4B -0.0206 0.7795 0.7862 0.058 Uiso calc R 1 . .
C C6 0.1306(2) 0.87500(17) 0.6073(2) 0.0418(6) Uani d . 1 . .
H H6 0.0821 0.9393 0.57 0.05 Uiso calc R 1 . .
C C11 0.4337(2) 1.1336(2) 0.9506(3) 0.0531(7) Uani d . 1 . .
H H11 0.4715 1.1828 1.0194 0.064 Uiso calc R 1 . .
O O4 0.32853(19) 0.84984(14) 0.5961(2) 0.0671(6) Uani d . 1 . .
C C13 0.2729(2) 1.00029(17) 0.8437(2) 0.0356(5) Uani d . 1 . .
C C9 0.4284(2) 1.0449(2) 0.7541(2) 0.0476(6) Uani d . 1 . .
C C3 -0.1215(2) 0.8927(2) 0.6495(3) 0.0561(7) Uani d . 1 . .
H H3A -0.1273 0.918 0.5628 0.067 Uiso calc R 1 . .
H H3B -0.2038 0.8634 0.6347 0.067 Uiso calc R 1 . .
C C7 0.2699(2) 0.89907(18) 0.6467(2) 0.0438(6) Uani d . 1 . .
C C14 0.1509(2) 0.94477(16) 0.8313(2) 0.0345(5) Uani d . 1 . .
C C8 0.3255(2) 0.98299(17) 0.7498(2) 0.0388(6) Uani d . 1 . .
C C12 0.3306(2) 1.07620(18) 0.9453(2) 0.0438(6) Uani d . 1 . .
C C5 0.1163(2) 0.84812(16) 0.7377(2) 0.0378(6) Uani d . 1 . .
C C10 0.4813(2) 1.1187(2) 0.8545(3) 0.0540(7) Uani d . 1 . .
H H10 0.5496 1.159 0.858 0.065 Uiso calc R 1 . .
C C15 0.5726(3) 1.0884(3) 0.6571(3) 0.0789(10) Uani d . 1 . .
H H15A 0.5527 1.1614 0.6544 0.118 Uiso calc R 1 . .
H H15B 0.5887 1.0709 0.5797 0.118 Uiso calc R 1 . .
H H15C 0.6472 1.0732 0.7394 0.118 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0654(12) 0.0456(10) 0.0352(8) -0.0112(8) 0.0256(8) -0.0018(7)
O2 0.0690(12) 0.0341(9) 0.0424(9) 0.0149(8) 0.0250(9) 0.0092(7)
O6 0.0743(13) 0.0579(11) 0.0530(10) -0.0233(9) 0.0371(10) -0.0237(9)
O3 0.0841(14) 0.0549(11) 0.0399(9) -0.0035(10) 0.0223(9) -0.0102(9)
O5 0.0627(13) 0.0978(16) 0.0730(13) -0.0138(11) 0.0477(11) 0.0021(12)
C1 0.0456(15) 0.0366(13) 0.0586(15) 0.0018(11) 0.0248(12) -0.0055(11)
C2 0.0458(16) 0.0620(18) 0.084(2) 0.0022(14) 0.0310(15) -0.0045(15)
C16 0.088(2) 0.0620(18) 0.0592(17) -0.0189(16) 0.0341(16) -0.0273(15)
C4 0.0598(16) 0.0419(14) 0.0425(13) -0.0126(12) 0.0207(12) -0.0011(11)
C6 0.0589(16) 0.0323(12) 0.0351(12) 0.0052(11) 0.0211(11) -0.0007(10)
C11 0.0497(16) 0.0482(15) 0.0547(15) -0.0108(12) 0.0158(13) -0.0058(12)
O4 0.0811(14) 0.0643(12) 0.0770(13) 0.0084(10) 0.0540(12) -0.0103(10)
C13 0.0366(12) 0.0321(12) 0.0370(11) 0.0017(10) 0.0147(10) 0.0039(10)
C9 0.0416(14) 0.0546(15) 0.0504(14) 0.0029(12) 0.0233(12) 0.0109(13)
C3 0.0437(15) 0.0616(17) 0.0589(16) -0.0069(13) 0.0179(13) 0.0059(14)
C7 0.0589(16) 0.0417(13) 0.0391(12) 0.0086(12) 0.0290(12) 0.0080(11)
C14 0.0407(13) 0.0323(11) 0.0333(11) -0.0024(10) 0.0183(10) 0.0004(10)
C8 0.0386(13) 0.0395(13) 0.0404(12) 0.0050(10) 0.0189(11) 0.0069(10)
C12 0.0471(15) 0.0419(14) 0.0426(13) -0.0042(11) 0.0193(11) -0.0023(11)
C5 0.0493(14) 0.0276(12) 0.0354(11) 0.0021(10) 0.0169(11) 0.0026(9)
C10 0.0414(15) 0.0546(16) 0.0644(16) -0.0086(13) 0.0210(13) 0.0104(14)
C15 0.0621(19) 0.098(2) 0.099(2) -0.0028(18) 0.0550(19) 0.022(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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C14 . 1.444(2) ?
O1 H1 . 0.82 ?
O2 C5 . 1.435(3) ?
O2 H2 . 0.82 ?
O6 C12 . 1.384(3) ?
O6 C16 . 1.427(3) ?
O3 C6 . 1.402(3) ?
O3 H3 . 0.82 ?
O5 C9 . 1.362(3) ?
O5 C15 . 1.428(3) ?
C1 C2 . 1.519(3) ?
C1 C14 . 1.541(3) ?
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C2 C3 . 1.510(4) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C4 C3 . 1.515(4) ?
C4 C5 . 1.538(3) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C6 C7 . 1.511(3) ?
C6 C5 . 1.533(3) ?
C6 H6 . 0.98 ?
C11 C12 . 1.381(3) ?
C11 C10 . 1.384(4) ?
C11 H11 . 0.93 ?
O4 C7 . 1.215(3) ?
C13 C12 . 1.405(3) ?
C13 C8 . 1.409(3) ?
C13 C14 . 1.533(3) ?
C9 C10 . 1.373(4) ?
C9 C8 . 1.414(3) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C7 C8 . 1.484(3) ?
C14 C5 . 1.540(3) ?
C10 H10 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O1 H1 . . 109.5 ?
C5 O2 H2 . . 109.5 ?
C12 O6 C16 . . 118.10(19) ?
C6 O3 H3 . . 109.5 ?
C9 O5 C15 . . 117.6(2) ?
C2 C1 C14 . . 114.4(2) ?
C2 C1 H1A . . 108.7 ?
C14 C1 H1A . . 108.7 ?
C2 C1 H1B . . 108.7 ?
C14 C1 H1B . . 108.7 ?
H1A C1 H1B . . 107.6 ?
C3 C2 C1 . . 110.7(2) ?
C3 C2 H2A . . 109.5 ?
C1 C2 H2A . . 109.5 ?
C3 C2 H2B . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 108.1 ?
O6 C16 H16A . . 109.5 ?
O6 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O6 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C3 C4 C5 . . 114.03(19) ?
C3 C4 H4A . . 108.7 ?
C5 C4 H4A . . 108.7 ?
C3 C4 H4B . . 108.7 ?
C5 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
O3 C6 C7 . . 113.04(18) ?
O3 C6 C5 . . 113.31(18) ?
C7 C6 C5 . . 107.87(18) ?
O3 C6 H6 . . 107.4 ?
C7 C6 H6 . . 107.4 ?
C5 C6 H6 . . 107.4 ?
C12 C11 C10 . . 120.6(2) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C12 C13 C8 . . 118.0(2) ?
C12 C13 C14 . . 120.01(18) ?
C8 C13 C14 . . 121.89(19) ?
O5 C9 C10 . . 123.8(2) ?
O5 C9 C8 . . 116.5(2) ?
C10 C9 C8 . . 119.7(2) ?
C2 C3 C4 . . 109.9(2) ?
C2 C3 H3A . . 109.7 ?
C4 C3 H3A . . 109.7 ?
C2 C3 H3B . . 109.7 ?
C4 C3 H3B . . 109.7 ?
H3A C3 H3B . . 108.2 ?
O4 C7 C8 . . 124.7(2) ?
O4 C7 C6 . . 120.0(2) ?
C8 C7 C6 . . 115.28(18) ?
O1 C14 C13 . . 111.04(17) ?
O1 C14 C5 . . 103.86(16) ?
C13 C14 C5 . . 113.63(17) ?
O1 C14 C1 . . 110.14(17) ?
C13 C14 C1 . . 107.21(17) ?
C5 C14 C1 . . 111.00(18) ?
C13 C8 C9 . . 120.3(2) ?
C13 C8 C7 . . 118.48(19) ?
C9 C8 C7 . . 121.19(19) ?
C11 C12 O6 . . 122.8(2) ?
C11 C12 C13 . . 120.9(2) ?
O6 C12 C13 . . 116.28(19) ?
O2 C5 C6 . . 103.38(17) ?
O2 C5 C4 . . 110.45(18) ?
C6 C5 C4 . . 110.98(18) ?
O2 C5 C14 . . 110.86(17) ?
C6 C5 C14 . . 109.15(17) ?
C4 C5 C14 . . 111.71(18) ?
C9 C10 C11 . . 120.5(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
O5 C15 H15A . . 109.5 ?
O5 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O5 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?