# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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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data_4I
_database_code_depnum_ccdc_archive 'CCDC 848918'
#TrackingRef '4I.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'4-O-benzyl-myo-inositol-1,3,5-orthoformate'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 O6'
_chemical_formula_sum            'C14 H16 O6'
_chemical_formula_weight         280.27

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   Pbca
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.460(5)
_cell_length_b                   11.536(5)
_cell_length_c                   42.364(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5112(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2240
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      19.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2368
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_process_details   "bruker's sadabs"

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24154
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4500
_reflns_number_gt                2952
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, Ortep32, mercury 2.3'
_computing_publication_material  'SHELXTL, Platon'

_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^)+(0.0590P)^2^+1.0327P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4500
_refine_ls_number_parameters     377
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.026
_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 0.65125(17) 0.24323(16) 0.25021(4) 0.0479(5) Uani 1 1 d . . .
O2 O 0.5865(2) 0.48566(19) 0.25273(5) 0.0581(6) Uani 1 1 d . . .
O3 O 0.49764(15) 0.29613(15) 0.21361(4) 0.0481(5) Uani 1 1 d . . .
O4 O 0.72782(19) 0.43277(17) 0.16114(4) 0.0583(6) Uani 1 1 d . . .
O5 O 0.64877(17) 0.15755(15) 0.20083(4) 0.0507(5) Uani 1 1 d . . .
O6 O 0.91708(18) 0.3639(2) 0.20404(5) 0.0559(5) Uani 1 1 d D . .
C1 C 0.7381(2) 0.3333(2) 0.23997(6) 0.0419(7) Uani 1 1 d . . .
H1 H 0.7909 0.3584 0.2578 0.050 Uiso 1 1 calc R . .
C2 C 0.6593(2) 0.4348(2) 0.22806(6) 0.0404(6) Uani 1 1 d . . .
H2 H 0.7173 0.4936 0.2195 0.048 Uiso 1 1 calc R . .
C3 C 0.5753(2) 0.3899(2) 0.20153(6) 0.0434(7) Uani 1 1 d . . .
H3 H 0.5200 0.4524 0.1939 0.052 Uiso 1 1 calc R . .
C4 C 0.6523(2) 0.3413(2) 0.17449(6) 0.0458(7) Uani 1 1 d . . .
H4 H 0.5943 0.3105 0.1584 0.055 Uiso 1 1 calc R . .
C5 C 0.7352(2) 0.2425(2) 0.18762(6) 0.0466(7) Uani 1 1 d . . .
H5 H 0.7858 0.2076 0.1706 0.056 Uiso 1 1 calc R . .
C6 C 0.8232(2) 0.2831(2) 0.21429(6) 0.0454(7) Uani 1 1 d . . .
H6 H 0.8673 0.2152 0.2229 0.054 Uiso 1 1 calc R . .
C7 C 0.5741(3) 0.2064(2) 0.22503(7) 0.0472(7) Uani 1 1 d . . .
H7 H 0.5172 0.1456 0.2330 0.057 Uiso 1 1 calc R . .
C8 C 0.7420(3) 0.4267(3) 0.12824(6) 0.0532(8) Uani 1 1 d . . .
H8A H 0.6593 0.4361 0.1182 0.064 Uiso 1 1 calc R . .
H8B H 0.7753 0.3512 0.1224 0.064 Uiso 1 1 calc R . .
C9 C 0.8316(2) 0.5196(2) 0.11675(6) 0.0425(7) Uani 1 1 d . . .
C10 C 0.8064(3) 0.5753(3) 0.08850(7) 0.0553(8) Uani 1 1 d . . .
H10 H 0.7328 0.5567 0.0773 0.066 Uiso 1 1 calc R . .
C11 C 0.8895(3) 0.6587(3) 0.07668(7) 0.0635(9) Uani 1 1 d . . .
H11 H 0.8710 0.6960 0.0578 0.076 Uiso 1 1 calc R . .
C12 C 0.9984(3) 0.6860(3) 0.09286(7) 0.0590(8) Uani 1 1 d . . .
H12 H 1.0542 0.7417 0.0850 0.071 Uiso 1 1 calc R . .
C13 C 1.0250(3) 0.6307(3) 0.12079(7) 0.0538(8) Uani 1 1 d . . .
H13 H 1.0993 0.6490 0.1318 0.065 Uiso 1 1 calc R . .
C14 C 0.9424(3) 0.5484(2) 0.13260(6) 0.0474(7) Uani 1 1 d . . .
H14 H 0.9616 0.5116 0.1516 0.057 Uiso 1 1 calc R . .
O9 O 0.15111(17) 0.36460(16) 0.00022(4) 0.0477(5) Uani 1 1 d . . .
O10 O -0.14313(18) 0.3171(2) 0.04554(5) 0.0594(6) Uani 1 1 d . . .
O11 O 0.18658(17) 0.42618(16) 0.05158(4) 0.0509(5) Uani 1 1 d . . .
O12 O 0.00994(16) 0.18038(16) 0.08513(4) 0.0475(5) Uani 1 1 d . . .
O7 O 0.27764(15) 0.25548(16) 0.03367(4) 0.0473(5) Uani 1 1 d . . .
O8 O 0.1229(2) 0.11542(19) -0.00874(5) 0.0593(6) Uani 1 1 d . . .
C17 C 0.0368(2) 0.3014(2) 0.00893(6) 0.0442(7) Uani 1 1 d . . .
H17 H -0.0228 0.3002 -0.0089 0.053 Uiso 1 1 calc R . .
C18 C -0.0236(2) 0.3658(2) 0.03662(6) 0.0470(7) Uani 1 1 d . . .
H18 H -0.0389 0.4460 0.0300 0.056 Uiso 1 1 calc R . .
C19 C 0.0737(2) 0.3679(2) 0.06327(6) 0.0442(7) Uani 1 1 d . . .
H19 H 0.0389 0.4098 0.0815 0.053 Uiso 1 1 calc R . .
C20 C 0.1155(2) 0.2460(2) 0.07318(6) 0.0414(7) Uani 1 1 d . . .
H20 H 0.1814 0.2519 0.0895 0.050 Uiso 1 1 calc R . .
C15 C 0.1710(2) 0.1865(2) 0.04441(6) 0.0417(7) Uani 1 1 d . . .
H15 H 0.2008 0.1089 0.0502 0.050 Uiso 1 1 calc R . .
C16 C 0.0747(2) 0.1777(2) 0.01759(6) 0.0428(7) Uani 1 1 d . . .
H16 H -0.0014 0.1374 0.0255 0.051 Uiso 1 1 calc R . .
C21 C 0.2380(3) 0.3682(2) 0.02534(6) 0.0468(7) Uani 1 1 d . . .
H21 H 0.3135 0.4113 0.0183 0.056 Uiso 1 1 calc R . .
C22 C -0.0043(3) 0.1888(3) 0.11924(7) 0.0580(8) Uani 1 1 d . . .
H22A H -0.0905 0.1659 0.1249 0.070 Uiso 1 1 calc R . .
H22B H 0.0069 0.2690 0.1255 0.070 Uiso 1 1 calc R . .
C23 C 0.0887(3) 0.1151(2) 0.13729(6) 0.0449(7) Uani 1 1 d . . .
C24 C 0.1306(3) 0.1495(3) 0.16720(7) 0.0514(7) Uani 1 1 d . . .
H24 H 0.1044 0.2202 0.1755 0.062 Uiso 1 1 calc R . .
C25 C 0.2117(3) 0.0778(3) 0.18453(7) 0.0529(8) Uani 1 1 d . . .
H25 H 0.2402 0.1007 0.2044 0.063 Uiso 1 1 calc R . .
C26 C 0.2492(3) -0.0260(3) 0.17234(7) 0.0557(8) Uani 1 1 d . . .
H26 H 0.3029 -0.0741 0.1839 0.067 Uiso 1 1 calc R . .
C27 C 0.2081(3) -0.0602(3) 0.14297(8) 0.0622(9) Uani 1 1 d . . .
H27 H 0.2343 -0.1311 0.1348 0.075 Uiso 1 1 calc R . .
C28 C 0.1284(3) 0.0098(3) 0.12567(7) 0.0571(8) Uani 1 1 d . . .
H28 H 0.1009 -0.0143 0.1059 0.068 Uiso 1 1 calc R . .
H2' H 0.542(3) 0.438(3) 0.2592(7) 0.066(12) Uiso 1 1 d . . .
H6' H 0.879(3) 0.417(3) 0.1933(8) 0.111(16) Uiso 1 1 d D . .
H10' H -0.129(4) 0.258(4) 0.0583(9) 0.113(16) Uiso 1 1 d . . .
H8' H 0.190(3) 0.146(4) -0.0137(9) 0.099(15) Uiso 1 1 d . . .

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 0.0584(12) 0.0426(11) 0.0427(11) 0.0100(9) 0.0071(9) -0.0003(10)
O2 0.0610(14) 0.0398(13) 0.0734(16) -0.0137(11) 0.0209(12) -0.0005(11)
O3 0.0356(10) 0.0417(11) 0.0670(13) 0.0073(9) 0.0043(9) -0.0054(8)
O4 0.0717(13) 0.0681(14) 0.0352(11) 0.0049(10) -0.0014(9) -0.0345(11)
O5 0.0593(12) 0.0337(11) 0.0591(12) -0.0069(9) 0.0131(10) -0.0024(9)
O6 0.0367(11) 0.0717(15) 0.0593(13) 0.0034(12) 0.0019(10) -0.0048(11)
C1 0.0454(15) 0.0440(17) 0.0364(15) 0.0006(12) 0.0004(12) -0.0011(13)
C2 0.0420(15) 0.0320(15) 0.0472(16) -0.0013(12) 0.0103(13) -0.0033(12)
C3 0.0383(15) 0.0346(16) 0.0573(18) 0.0123(13) -0.0003(13) 0.0000(12)
C4 0.0474(16) 0.0496(18) 0.0403(16) 0.0035(13) -0.0052(13) -0.0162(14)
C5 0.0482(16) 0.0469(17) 0.0447(16) -0.0054(14) 0.0113(13) -0.0047(14)
C6 0.0361(15) 0.0499(18) 0.0502(17) 0.0043(14) 0.0042(12) 0.0063(13)
C7 0.0523(17) 0.0343(16) 0.0550(18) 0.0039(14) 0.0088(15) -0.0035(14)
C8 0.0583(18) 0.064(2) 0.0371(16) 0.0041(14) 0.0005(14) -0.0052(15)
C9 0.0471(16) 0.0467(17) 0.0338(15) 0.0022(13) 0.0076(12) 0.0073(13)
C10 0.0514(17) 0.073(2) 0.0416(17) 0.0091(16) 0.0024(14) 0.0121(16)
C11 0.067(2) 0.077(2) 0.0465(18) 0.0269(17) 0.0174(16) 0.0165(18)
C12 0.063(2) 0.057(2) 0.058(2) 0.0116(16) 0.0220(17) 0.0021(16)
C13 0.0518(17) 0.059(2) 0.0508(18) 0.0002(15) 0.0078(14) -0.0048(15)
C14 0.0528(17) 0.0534(18) 0.0360(15) 0.0098(13) 0.0010(13) 0.0012(14)
O9 0.0505(11) 0.0504(12) 0.0423(11) 0.0081(9) 0.0017(9) -0.0037(9)
O10 0.0387(11) 0.0726(16) 0.0670(15) 0.0126(12) 0.0025(10) 0.0050(10)
O11 0.0553(12) 0.0431(12) 0.0543(12) -0.0111(9) 0.0123(9) -0.0117(9)
O12 0.0467(11) 0.0576(13) 0.0382(11) 0.0092(9) -0.0026(8) -0.0080(9)
O7 0.0376(10) 0.0524(12) 0.0521(12) -0.0013(9) 0.0006(9) 0.0033(9)
O8 0.0684(15) 0.0554(14) 0.0540(14) -0.0185(10) 0.0050(11) -0.0073(12)
C17 0.0390(15) 0.0517(18) 0.0420(16) 0.0054(13) -0.0034(12) -0.0029(13)
C18 0.0414(15) 0.0421(17) 0.0575(18) 0.0088(14) 0.0044(13) 0.0058(13)
C19 0.0446(15) 0.0427(17) 0.0454(16) -0.0048(13) 0.0100(13) -0.0027(13)
C20 0.0366(14) 0.0502(17) 0.0374(15) 0.0047(13) -0.0043(12) -0.0053(13)
C15 0.0411(15) 0.0331(15) 0.0509(17) 0.0023(12) -0.0003(12) 0.0030(12)
C16 0.0474(16) 0.0381(16) 0.0429(16) -0.0045(13) 0.0013(13) -0.0045(13)
C21 0.0440(16) 0.0470(18) 0.0494(17) -0.0038(14) 0.0057(13) -0.0075(14)
C22 0.0592(19) 0.061(2) 0.0542(19) 0.0035(15) 0.0108(15) 0.0001(16)
C23 0.0438(15) 0.0507(18) 0.0400(16) 0.0152(14) 0.0005(12) -0.0047(14)
C24 0.0589(18) 0.0405(17) 0.0549(19) -0.0023(14) 0.0095(15) -0.0048(14)
C25 0.0591(18) 0.060(2) 0.0392(16) -0.0004(15) -0.0042(14) -0.0039(16)
C26 0.0614(19) 0.057(2) 0.0483(18) 0.0088(15) 0.0024(15) 0.0080(16)
C27 0.069(2) 0.057(2) 0.060(2) -0.0062(17) 0.0094(17) 0.0093(17)
C28 0.0634(19) 0.067(2) 0.0409(18) -0.0108(16) 0.0033(15) -0.0047(17)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.404(3) . ?
O1 C1 1.447(3) . ?
O2 C2 1.420(3) . ?
O2 H2' 0.77(3) . ?
O3 C7 1.395(3) . ?
O3 C3 1.446(3) . ?
O4 C8 1.404(3) . ?
O4 C4 1.435(3) . ?
O5 C7 1.406(3) . ?
O5 C5 1.446(3) . ?
O6 C6 1.422(3) . ?
O6 H6' 0.860(19) . ?
C1 C2 1.519(4) . ?
C1 C6 1.520(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.517(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.509(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.536(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.531(4) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C7 H7 0.9800 . ?
C8 C9 1.504(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.380(4) . ?
C9 C10 1.384(4) . ?
C10 C11 1.390(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
O9 C21 1.400(3) . ?
O9 C17 1.448(3) . ?
O10 C18 1.422(3) . ?
O10 H10' 0.88(4) . ?
O11 C21 1.404(3) . ?
O11 C19 1.446(3) . ?
O12 C20 1.431(3) . ?
O12 C22 1.456(3) . ?
O7 C21 1.410(3) . ?
O7 C15 1.444(3) . ?
O8 C16 1.419(3) . ?
O8 H8' 0.81(4) . ?
C17 C18 1.525(4) . ?
C17 C16 1.526(4) . ?
C17 H17 0.9800 . ?
C18 C19 1.520(4) . ?
C18 H18 0.9800 . ?
C19 C20 1.531(4) . ?
C19 H19 0.9800 . ?
C20 C15 1.514(4) . ?
C20 H20 0.9800 . ?
C15 C16 1.522(4) . ?
C15 H15 0.9800 . ?
C16 H16 0.9800 . ?
C21 H21 0.9800 . ?
C22 C23 1.501(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C28 1.375(4) . ?
C23 C24 1.398(4) . ?
C24 C25 1.394(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.361(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.374(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.372(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
C7 O1 C1 110.53(19) . . ?
C2 O2 H2' 107(2) . . ?
C7 O3 C3 110.85(19) . . ?
C8 O4 C4 114.4(2) . . ?
C7 O5 C5 111.0(2) . . ?
C6 O6 H6' 108(3) . . ?
O1 C1 C2 108.21(19) . . ?
O1 C1 C6 108.0(2) . . ?
C2 C1 C6 112.0(2) . . ?
O1 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
C6 C1 H1 109.5 . . ?
O2 C2 C3 112.1(2) . . ?
O2 C2 C1 111.4(2) . . ?
C3 C2 C1 107.3(2) . . ?
O2 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
O3 C3 C4 106.9(2) . . ?
O3 C3 C2 108.6(2) . . ?
C4 C3 C2 112.4(2) . . ?
O3 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
O4 C4 C3 108.6(2) . . ?
O4 C4 C5 112.2(2) . . ?
C3 C4 C5 107.6(2) . . ?
O4 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
O5 C5 C6 107.3(2) . . ?
O5 C5 C4 106.8(2) . . ?
C6 C5 C4 112.3(2) . . ?
O5 C5 H5 110.1 . . ?
C6 C5 H5 110.1 . . ?
C4 C5 H5 110.1 . . ?
O6 C6 C1 111.9(2) . . ?
O6 C6 C5 113.0(2) . . ?
C1 C6 C5 107.0(2) . . ?
O6 C6 H6 108.3 . . ?
C1 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
O3 C7 O1 111.6(2) . . ?
O3 C7 O5 111.3(2) . . ?
O1 C7 O5 110.9(2) . . ?
O3 C7 H7 107.6 . . ?
O1 C7 H7 107.6 . . ?
O5 C7 H7 107.6 . . ?
O4 C8 C9 110.6(2) . . ?
O4 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C14 C9 C10 118.0(3) . . ?
C14 C9 C8 122.5(2) . . ?
C10 C9 C8 119.5(3) . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C21 O9 C17 110.91(19) . . ?
C18 O10 H10' 109(2) . . ?
C21 O11 C19 111.22(19) . . ?
C20 O12 C22 113.3(2) . . ?
C21 O7 C15 111.06(18) . . ?
C16 O8 H8' 107(3) . . ?
O9 C17 C18 107.1(2) . . ?
O9 C17 C16 108.5(2) . . ?
C18 C17 C16 112.2(2) . . ?
O9 C17 H17 109.7 . . ?
C18 C17 H17 109.7 . . ?
C16 C17 H17 109.7 . . ?
O10 C18 C19 113.4(2) . . ?
O10 C18 C17 112.1(2) . . ?
C19 C18 C17 107.5(2) . . ?
O10 C18 H18 107.8 . . ?
C19 C18 H18 107.8 . . ?
C17 C18 H18 107.8 . . ?
O11 C19 C18 107.5(2) . . ?
O11 C19 C20 106.7(2) . . ?
C18 C19 C20 112.3(2) . . ?
O11 C19 H19 110.1 . . ?
C18 C19 H19 110.1 . . ?
C20 C19 H19 110.1 . . ?
O12 C20 C15 109.9(2) . . ?
O12 C20 C19 111.3(2) . . ?
C15 C20 C19 107.7(2) . . ?
O12 C20 H20 109.3 . . ?
C15 C20 H20 109.3 . . ?
C19 C20 H20 109.3 . . ?
O7 C15 C20 107.5(2) . . ?
O7 C15 C16 108.2(2) . . ?
C20 C15 C16 112.2(2) . . ?
O7 C15 H15 109.6 . . ?
C20 C15 H15 109.6 . . ?
C16 C15 H15 109.6 . . ?
O8 C16 C15 112.7(2) . . ?
O8 C16 C17 112.1(2) . . ?
C15 C16 C17 106.8(2) . . ?
O8 C16 H16 108.4 . . ?
C15 C16 H16 108.4 . . ?
C17 C16 H16 108.4 . . ?
O9 C21 O11 111.6(2) . . ?
O9 C21 O7 110.7(2) . . ?
O11 C21 O7 110.7(2) . . ?
O9 C21 H21 107.9 . . ?
O11 C21 H21 107.9 . . ?
O7 C21 H21 107.9 . . ?
O12 C22 C23 113.7(2) . . ?
O12 C22 H22A 108.8 . . ?
C23 C22 H22A 108.8 . . ?
O12 C22 H22B 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C28 C23 C24 118.7(3) . . ?
C28 C23 C22 120.9(3) . . ?
C24 C23 C22 120.3(3) . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C23 120.8(3) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?

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
C7 O1 C1 C2 60.3(3) . . . . ?
C7 O1 C1 C6 -61.1(3) . . . . ?
O1 C1 C2 O2 64.9(3) . . . . ?
C6 C1 C2 O2 -176.2(2) . . . . ?
O1 C1 C2 C3 -58.1(3) . . . . ?
C6 C1 C2 C3 60.8(3) . . . . ?
C7 O3 C3 C4 61.8(3) . . . . ?
C7 O3 C3 C2 -59.6(3) . . . . ?
O2 C2 C3 O3 -64.9(3) . . . . ?
C1 C2 C3 O3 57.7(2) . . . . ?
O2 C2 C3 C4 177.1(2) . . . . ?
C1 C2 C3 C4 -60.3(3) . . . . ?
C8 O4 C4 C3 -143.9(2) . . . . ?
C8 O4 C4 C5 97.3(3) . . . . ?
O3 C3 C4 O4 178.16(19) . . . . ?
C2 C3 C4 O4 -62.9(3) . . . . ?
O3 C3 C4 C5 -60.2(2) . . . . ?
C2 C3 C4 C5 58.8(3) . . . . ?
C7 O5 C5 C6 60.9(3) . . . . ?
C7 O5 C5 C4 -59.8(3) . . . . ?
O4 C4 C5 O5 178.9(2) . . . . ?
C3 C4 C5 O5 59.5(3) . . . . ?
O4 C4 C5 C6 61.5(3) . . . . ?
C3 C4 C5 C6 -57.9(3) . . . . ?
O1 C1 C6 O6 -176.6(2) . . . . ?
C2 C1 C6 O6 64.4(3) . . . . ?
O1 C1 C6 C5 59.2(3) . . . . ?
C2 C1 C6 C5 -59.9(3) . . . . ?
O5 C5 C6 O6 177.5(2) . . . . ?
C4 C5 C6 O6 -65.4(3) . . . . ?
O5 C5 C6 C1 -58.8(3) . . . . ?
C4 C5 C6 C1 58.3(3) . . . . ?
C3 O3 C7 O1 61.7(3) . . . . ?
C3 O3 C7 O5 -62.7(3) . . . . ?
C1 O1 C7 O3 -62.2(3) . . . . ?
C1 O1 C7 O5 62.5(3) . . . . ?
C5 O5 C7 O3 62.0(3) . . . . ?
C5 O5 C7 O1 -62.8(3) . . . . ?
C4 O4 C8 C9 -175.1(2) . . . . ?
O4 C8 C9 C14 41.1(4) . . . . ?
O4 C8 C9 C10 -142.1(3) . . . . ?
C14 C9 C10 C11 -0.8(4) . . . . ?
C8 C9 C10 C11 -177.8(3) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C9 0.0(4) . . . . ?
C10 C9 C14 C13 0.5(4) . . . . ?
C8 C9 C14 C13 177.4(3) . . . . ?
C21 O9 C17 C18 60.9(3) . . . . ?
C21 O9 C17 C16 -60.4(3) . . . . ?
O9 C17 C18 O10 174.9(2) . . . . ?
C16 C17 C18 O10 -66.1(3) . . . . ?
O9 C17 C18 C19 -59.7(3) . . . . ?
C16 C17 C18 C19 59.3(3) . . . . ?
C21 O11 C19 C18 -59.8(3) . . . . ?
C21 O11 C19 C20 60.9(3) . . . . ?
O10 C18 C19 O11 -176.2(2) . . . . ?
C17 C18 C19 O11 59.2(3) . . . . ?
O10 C18 C19 C20 66.7(3) . . . . ?
C17 C18 C19 C20 -57.9(3) . . . . ?
C22 O12 C20 C15 148.2(2) . . . . ?
C22 O12 C20 C19 -92.6(2) . . . . ?
O11 C19 C20 O12 -179.88(19) . . . . ?
C18 C19 C20 O12 -62.4(3) . . . . ?
O11 C19 C20 C15 -59.3(3) . . . . ?
C18 C19 C20 C15 58.2(3) . . . . ?
C21 O7 C15 C20 -60.6(3) . . . . ?
C21 O7 C15 C16 60.8(3) . . . . ?
O12 C20 C15 O7 -179.24(18) . . . . ?
C19 C20 C15 O7 59.3(2) . . . . ?
O12 C20 C15 C16 61.9(3) . . . . ?
C19 C20 C15 C16 -59.5(3) . . . . ?
O7 C15 C16 O8 65.5(3) . . . . ?
C20 C15 C16 O8 -176.1(2) . . . . ?
O7 C15 C16 C17 -58.1(3) . . . . ?
C20 C15 C16 C17 60.3(3) . . . . ?
O9 C17 C16 O8 -65.9(3) . . . . ?
C18 C17 C16 O8 176.0(2) . . . . ?
O9 C17 C16 C15 58.0(3) . . . . ?
C18 C17 C16 C15 -60.1(3) . . . . ?
C17 O9 C21 O11 -61.9(3) . . . . ?
C17 O9 C21 O7 61.9(3) . . . . ?
C19 O11 C21 O9 61.3(3) . . . . ?
C19 O11 C21 O7 -62.5(3) . . . . ?
C15 O7 C21 O9 -62.3(3) . . . . ?
C15 O7 C21 O11 62.0(3) . . . . ?
C20 O12 C22 C23 -77.7(3) . . . . ?
O12 C22 C23 C28 -34.0(4) . . . . ?
O12 C22 C23 C24 149.8(2) . . . . ?
C28 C23 C24 C25 0.4(4) . . . . ?
C22 C23 C24 C25 176.6(2) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C27 0.4(4) . . . . ?
C25 C26 C27 C28 -0.3(5) . . . . ?
C26 C27 C28 C23 0.2(5) . . . . ?
C24 C23 C28 C27 -0.3(4) . . . . ?
C22 C23 C28 C27 -176.5(3) . . . . ?
C1 C6 O6 H6' -72(3) . . . . ?
C17 C18 O10 H10' 84(3) . . . . ?
C15 C16 O8 H8' -54(3) . . . . ?
C1 C2 O2 H2' -60(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
O8 H8' O10 0.81(4) 2.25(4) 3.005(3) 155(4) 3
C7 H7 O2 0.98 2.22 3.192(3) 169.6 4_645
O2 H2' O6 0.77(3) 2.20(3) 2.910(3) 153(3) 6_556
C2 H2 O5 0.98 2.48 3.459(3) 174.0 7_765
C17 H17 O7 0.98 2.42 3.322(3) 152.4 3_455
C15 H15 O11 0.98 2.41 3.367(3) 163.7 7_655
C11 H11 O9 0.93 2.56 3.296(4) 135.9 5_665
C1 H1 O3 0.98 2.58 3.379(3) 138.8 6_656

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.042


data_4II
_database_code_depnum_ccdc_archive 'CCDC 848919'
#TrackingRef '4II.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'4-O-benzyl-myo-inositol-1,3,5-orthoformate'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 O6'
_chemical_formula_sum            'C14 H16 O6'
_chemical_formula_weight         280.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   10.4043(17)
_cell_length_b                   13.720(2)
_cell_length_c                   10.3515(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.031(3)
_cell_angle_gamma                90.00
_cell_volume                     1304.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    795
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      19.71

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   "bruker's sadabs"

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6531
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2307
_reflns_number_gt                1591
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, Ortep32, mercury 2.3'
_computing_publication_material  'SHELXTL, Platon'

_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^)+(0.0408P)^2^+0.6159P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2307
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_restrained_S_all      1.224
_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 0.6543(3) 0.23214(17) 0.3767(3) 0.0389(7) Uani 1 1 d . . .
O2 O 0.3481(4) 0.2818(2) 0.2576(4) 0.0520(9) Uani 1 1 d . . .
O3 O 0.5319(3) 0.13344(18) 0.4625(3) 0.0433(8) Uani 1 1 d . . .
O4 O 0.3608(3) -0.00922(17) 0.1222(3) 0.0330(7) Uani 1 1 d . . .
O5 O 0.7109(3) 0.06764(19) 0.4168(3) 0.0436(7) Uani 1 1 d . . .
O6 O 0.5113(3) 0.11439(18) 0.0226(3) 0.0361(7) Uani 1 1 d . . .
C1 C 0.5483(4) 0.2159(3) 0.2262(4) 0.0355(10) Uani 1 1 d . . .
H1 H 0.5429 0.2733 0.1677 0.043 Uiso 1 1 calc R . .
C2 C 0.4010(4) 0.1974(3) 0.2178(4) 0.0336(10) Uani 1 1 d . . .
H2 H 0.3318 0.1796 0.1170 0.040 Uiso 1 1 calc R . .
C3 C 0.4187(4) 0.1112(3) 0.3166(4) 0.0340(10) Uani 1 1 d . . .
H3 H 0.3269 0.0992 0.3189 0.041 Uiso 1 1 calc R . .
C4 C 0.4643(4) 0.0201(2) 0.2663(4) 0.0318(9) Uani 1 1 d . . .
H4 H 0.4780 -0.0331 0.3348 0.038 Uiso 1 1 calc R . .
C5 C 0.6085(4) 0.0413(3) 0.2678(4) 0.0333(10) Uani 1 1 d . . .
H5 H 0.6427 -0.0163 0.2371 0.040 Uiso 1 1 calc R . .
C6 C 0.6020(4) 0.1294(3) 0.1745(4) 0.0317(9) Uani 1 1 d . . .
H6 H 0.7008 0.1435 0.1908 0.038 Uiso 1 1 calc R . .
C7 C 0.6644(5) 0.1507(3) 0.4620(4) 0.0423(11) Uani 1 1 d . . .
H7 H 0.7375 0.1651 0.5628 0.051 Uiso 1 1 calc R . .
C8 C 0.2258(4) -0.0455(3) 0.1090(4) 0.0402(11) Uani 1 1 d . . .
H8A H 0.1818 0.0026 0.1447 0.048 Uiso 1 1 calc R . .
H8B H 0.2427 -0.1045 0.1664 0.048 Uiso 1 1 calc R . .
C9 C 0.1269(4) -0.0665(3) -0.0495(4) 0.0357(10) Uani 1 1 d . . .
C10 C 0.0539(5) -0.1539(3) -0.0947(5) 0.0509(12) Uani 1 1 d . . .
H10 H 0.0662 -0.2015 -0.0258 0.061 Uiso 1 1 calc R . .
C11 C -0.0377(5) -0.1717(4) -0.2417(6) 0.0634(14) Uani 1 1 d . . .
H11 H -0.0866 -0.2309 -0.2707 0.076 Uiso 1 1 calc R . .
C12 C -0.0566(5) -0.1027(5) -0.3442(6) 0.0722(16) Uani 1 1 d . . .
H12 H -0.1174 -0.1150 -0.4429 0.087 Uiso 1 1 calc R . .
C13 C 0.0142(5) -0.0157(4) -0.3009(5) 0.0667(15) Uani 1 1 d . . .
H13 H 0.0009 0.0316 -0.3705 0.080 Uiso 1 1 calc R . .
C14 C 0.1052(5) 0.0029(3) -0.1553(5) 0.0494(12) Uani 1 1 d . . .
H14 H 0.1527 0.0627 -0.1275 0.059 Uiso 1 1 calc R . .
H6' H 0.557(7) 0.080(4) -0.019(6) 0.13(2) Uiso 1 1 d . . .
H2' H 0.411(6) 0.293(4) 0.344(6) 0.09(2) Uiso 1 1 d . . .

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 0.0494(19) 0.0347(16) 0.0330(16) -0.0045(12) 0.0196(14) -0.0119(13)
O2 0.054(2) 0.0405(19) 0.055(2) -0.0145(16) 0.0207(19) 0.0107(15)
O3 0.060(2) 0.0490(18) 0.0282(16) -0.0065(12) 0.0271(15) -0.0122(15)
O4 0.0317(16) 0.0374(15) 0.0316(15) -0.0040(12) 0.0163(13) -0.0057(12)
O5 0.0387(18) 0.0449(18) 0.0323(16) -0.0048(13) 0.0044(13) 0.0027(14)
O6 0.0499(19) 0.0364(16) 0.0265(16) -0.0008(12) 0.0218(14) -0.0026(14)
C1 0.052(3) 0.028(2) 0.025(2) -0.0015(16) 0.017(2) -0.0070(19)
C2 0.041(3) 0.026(2) 0.030(2) -0.0092(17) 0.0140(19) 0.0012(18)
C3 0.036(3) 0.035(2) 0.037(2) -0.0021(18) 0.022(2) -0.0075(19)
C4 0.046(3) 0.026(2) 0.025(2) 0.0029(16) 0.0184(19) -0.0044(19)
C5 0.034(2) 0.031(2) 0.029(2) -0.0032(17) 0.0102(19) 0.0001(18)
C6 0.033(2) 0.036(2) 0.027(2) -0.0062(17) 0.0147(19) -0.0066(18)
C7 0.046(3) 0.048(3) 0.028(2) -0.009(2) 0.013(2) -0.009(2)
C8 0.041(3) 0.039(2) 0.049(3) -0.0045(19) 0.027(2) -0.008(2)
C9 0.026(2) 0.040(2) 0.041(2) -0.003(2) 0.0156(19) 0.0052(19)
C10 0.030(3) 0.051(3) 0.062(3) -0.006(2) 0.013(2) 0.000(2)
C11 0.035(3) 0.066(3) 0.075(4) -0.032(3) 0.014(3) -0.013(3)
C12 0.045(3) 0.109(5) 0.046(3) -0.013(3) 0.007(3) 0.009(3)
C13 0.046(3) 0.099(4) 0.046(3) 0.009(3) 0.014(3) 0.012(3)
C14 0.039(3) 0.058(3) 0.047(3) 0.000(2) 0.017(2) -0.002(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
O1 C7 1.397(4) . ?
O1 C1 1.441(4) . ?
O2 C2 1.424(4) . ?
O2 H2' 0.84(5) . ?
O3 C7 1.401(5) . ?
O3 C3 1.445(4) . ?
O4 C4 1.427(4) . ?
O4 C8 1.435(4) . ?
O5 C7 1.402(4) . ?
O5 C5 1.449(4) . ?
O6 C6 1.418(4) . ?
O6 H6' 0.91(6) . ?
C1 C6 1.512(5) . ?
C1 C2 1.515(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.517(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.514(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.522(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.528(5) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C7 H7 0.9800 . ?
C8 C9 1.499(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.379(5) . ?
C9 C14 1.388(5) . ?
C10 C11 1.385(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
C7 O1 C1 110.6(3) . . ?
C2 O2 H2' 104(4) . . ?
C7 O3 C3 110.6(3) . . ?
C4 O4 C8 114.9(3) . . ?
C7 O5 C5 111.2(3) . . ?
C6 O6 H6' 112(4) . . ?
O1 C1 C6 106.4(3) . . ?
O1 C1 C2 109.1(3) . . ?
C6 C1 C2 112.3(3) . . ?
O1 C1 H1 109.6 . . ?
C6 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
O2 C2 C1 111.4(3) . . ?
O2 C2 C3 112.3(3) . . ?
C1 C2 C3 107.0(3) . . ?
O2 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
O3 C3 C4 107.5(3) . . ?
O3 C3 C2 108.7(3) . . ?
C4 C3 C2 111.7(3) . . ?
O3 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
C2 C3 H3 109.6 . . ?
O4 C4 C3 112.8(3) . . ?
O4 C4 C5 108.7(3) . . ?
C3 C4 C5 107.8(3) . . ?
O4 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
O5 C5 C4 106.7(3) . . ?
O5 C5 C6 105.5(3) . . ?
C4 C5 C6 113.2(3) . . ?
O5 C5 H5 110.4 . . ?
C4 C5 H5 110.4 . . ?
C6 C5 H5 110.4 . . ?
O6 C6 C1 110.0(3) . . ?
O6 C6 C5 113.3(3) . . ?
C1 C6 C5 108.1(3) . . ?
O6 C6 H6 108.4 . . ?
C1 C6 H6 108.4 . . ?
C5 C6 H6 108.4 . . ?
O1 C7 O3 110.8(3) . . ?
O1 C7 O5 112.0(3) . . ?
O3 C7 O5 111.0(3) . . ?
O1 C7 H7 107.6 . . ?
O3 C7 H7 107.6 . . ?
O5 C7 H7 107.6 . . ?
O4 C8 C9 108.0(3) . . ?
O4 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O4 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C10 C9 C14 118.0(4) . . ?
C10 C9 C8 121.6(4) . . ?
C14 C9 C8 120.4(4) . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.4(5) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.5(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.7(5) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.7(5) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?

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
C7 O1 C1 C6 -61.2(4) . . . . ?
C7 O1 C1 C2 60.3(4) . . . . ?
O1 C1 C2 O2 66.2(4) . . . . ?
C6 C1 C2 O2 -176.1(3) . . . . ?
O1 C1 C2 C3 -56.9(4) . . . . ?
C6 C1 C2 C3 60.8(4) . . . . ?
C7 O3 C3 C4 60.8(4) . . . . ?
C7 O3 C3 C2 -60.3(4) . . . . ?
O2 C2 C3 O3 -65.8(4) . . . . ?
C1 C2 C3 O3 56.8(4) . . . . ?
O2 C2 C3 C4 175.8(3) . . . . ?
C1 C2 C3 C4 -61.6(4) . . . . ?
C8 O4 C4 C3 -69.3(4) . . . . ?
C8 O4 C4 C5 171.2(3) . . . . ?
O3 C3 C4 O4 -179.7(3) . . . . ?
C2 C3 C4 O4 -60.5(4) . . . . ?
O3 C3 C4 C5 -59.6(3) . . . . ?
C2 C3 C4 C5 59.5(4) . . . . ?
C7 O5 C5 C4 -60.6(4) . . . . ?
C7 O5 C5 C6 60.1(4) . . . . ?
O4 C4 C5 O5 -178.2(3) . . . . ?
C3 C4 C5 O5 59.2(3) . . . . ?
O4 C4 C5 C6 66.2(4) . . . . ?
C3 C4 C5 C6 -56.4(4) . . . . ?
O1 C1 C6 O6 -174.1(3) . . . . ?
C2 C1 C6 O6 66.5(4) . . . . ?
O1 C1 C6 C5 61.7(4) . . . . ?
C2 C1 C6 C5 -57.6(4) . . . . ?
O5 C5 C6 O6 176.9(3) . . . . ?
C4 C5 C6 O6 -66.7(4) . . . . ?
O5 C5 C6 C1 -60.8(4) . . . . ?
C4 C5 C6 C1 55.5(4) . . . . ?
C1 O1 C7 O3 -62.7(4) . . . . ?
C1 O1 C7 O5 61.9(4) . . . . ?
C3 O3 C7 O1 62.9(4) . . . . ?
C3 O3 C7 O5 -62.2(4) . . . . ?
C5 O5 C7 O1 -61.8(4) . . . . ?
C5 O5 C7 O3 62.6(4) . . . . ?
C4 O4 C8 C9 176.3(3) . . . . ?
O4 C8 C9 C10 131.0(4) . . . . ?
O4 C8 C9 C14 -49.8(5) . . . . ?
C14 C9 C10 C11 0.4(6) . . . . ?
C8 C9 C10 C11 179.6(4) . . . . ?
C9 C10 C11 C12 0.2(7) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C11 C12 C13 C14 0.5(8) . . . . ?
C12 C13 C14 C9 0.1(7) . . . . ?
C10 C9 C14 C13 -0.5(6) . . . . ?
C8 C9 C14 C13 -179.7(4) . . . . ?
C1 C2 O2 H2' -61(4) . . . . ?
C1 C6 O6 H6' 158(4) . . . . ?

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
O6 H6' O4 0.91(6) 1.91(6) 2.824(4) 175(6) 3_655
C4 H4 O3 0.98 2.55 3.496(4) 161.5 3_656
O2 H2' O6 0.84(5) 2.07(5) 2.838(4) 151(5) 4_566
C1 H1 O3 0.98 2.44 3.365(4) 158.0 4_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.051