# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_platon_acc
_database_code_depnum_ccdc_archive 'CCDC 1026652'
_audit_update_record             
;
2014-09-28 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_audit_creation_date             2014-09-28T16:30:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
(1R,2R,6R,8S,10R,14S)-5,7,9,11- tetraoxatetracyclo[6.6.0.0^{2,6}.0^{10,14}]
        tetradecan-4- one
;
_chemical_formula_moiety         'C10 H12 O5'
_chemical_formula_sum            'C10 H12 O5'
_chemical_formula_weight         212.2
_chemical_compound_source        'see text'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 32 2 1'
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_Int_Tables_number      154
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y,x-y,2/3+z
-x+y,-x,1/3+z
y,x,-z
-x,-x+y,2/3-z
x-y,-y,1/3-z

_cell_length_a                   6.0046(6)
_cell_length_b                   6.0046(6)
_cell_length_c                   45.980(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1435.7(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    815
_cell_measurement_theta_min      2.8807
_cell_measurement_theta_max      70.7416
_cell_special_details            
;
;

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             672
_exptl_special_details           
;
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.88416
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 16.1293
_diffrn_orient_matrix_ub_11      -0.2521318
_diffrn_orient_matrix_ub_12      -0.1037794
_diffrn_orient_matrix_ub_13      -0.0173145
_diffrn_orient_matrix_ub_21      0.1243071
_diffrn_orient_matrix_ub_22      -0.0604384
_diffrn_orient_matrix_ub_23      -0.0258902
_diffrn_orient_matrix_ub_31      -0.0929707
_diffrn_orient_matrix_ub_32      -0.2706268
_diffrn_orient_matrix_ub_33      0.0124296
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_number            3117
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         70.88
_diffrn_reflns_theta_full        70.88
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_reflns_number_total             1752
_reflns_number_gt                1454
_reflns_threshold_expression     I>2σ(I)
_diffrn_reflns_reduction_process 
;
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'PLATON (Spek, 2003) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0433P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_number_reflns         1752
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.042
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.033

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4250(5) -0.3426(5) 0.30369(5) 0.0585(7) Uani 1 1 d . . .
C10 C 0.7722(5) 0.0289(5) 0.28712(5) 0.0534(6) Uani 1 1 d . . .
C2 C 0.3202(5) -0.1718(6) 0.29579(5) 0.0643(7) Uani 1 1 d . . .
C3 C 0.5386(5) 0.0561(5) 0.28011(5) 0.0519(6) Uani 1 1 d . . .
C4 C 0.5240(4) 0.0473(4) 0.24660(5) 0.0490(5) Uani 1 1 d . . .
C5 C 0.4896(5) 0.2581(5) 0.23283(5) 0.0568(6) Uani 1 1 d . . .
C6 C 0.3790(5) 0.2050(6) 0.20184(6) 0.0793(9) Uani 1 1 d . . .
C7 C 0.6142(6) 0.3503(6) 0.18277(6) 0.0796(9) Uani 1 1 d . . .
C8 C 0.7661(5) 0.4809(5) 0.22835(6) 0.0607(6) Uani 1 1 d . . .
C9 C 0.7948(4) 0.1136(5) 0.23775(5) 0.0524(6) Uani 1 1 d . . .
H10 H 0.8827 0.1564 0.3016 0.064 Uiso 1 1 calc R . .
H2A H 0.2698 -0.1154 0.3131 0.077 Uiso 1 1 calc R . .
H2B H 0.1718 -0.261 0.2832 0.077 Uiso 1 1 calc R . .
H3 H 0.5609 0.219 0.2875 0.062 Uiso 1 1 calc R . .
H4 H 0.395 -0.1233 0.2396 0.059 Uiso 1 1 calc R . .
H5 H 0.3926 0.3092 0.2457 0.068 Uiso 1 1 calc R . .
H6A H 0.2906 0.0225 0.1975 0.095 Uiso 1 1 calc R . .
H6B H 0.2604 0.2688 0.1992 0.095 Uiso 1 1 calc R . .
H7A H 0.6905 0.2451 0.1783 0.096 Uiso 1 1 calc R . .
H7B H 0.5703 0.4028 0.1647 0.096 Uiso 1 1 calc R . .
H8 H 0.8054 0.6205 0.2421 0.073 Uiso 1 1 calc R . .
H9 H 0.7917 0.0192 0.2202 0.063 Uiso 1 1 calc R . .
O1 O 0.3176(4) -0.5526(4) 0.31435(4) 0.0824(6) Uani 1 1 d . . .
O2 O 0.7849(4) 0.5676(4) 0.19954(4) 0.0748(6) Uani 1 1 d . . .
O3 O 0.9317(3) 0.3797(4) 0.23291(4) 0.0678(5) Uani 1 1 d . . .
O4 O 0.9073(3) 0.0553(4) 0.26125(4) 0.0663(5) Uani 1 1 d . . .
O5 O 0.6774(3) -0.2273(3) 0.29764(4) 0.0627(5) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C10 H10 0.98 . ?
C2 C1 1.492(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C10 1.525(3) . ?
C3 C2 1.522(3) . ?
C3 C4 1.543(3) . ?
C3 H3 0.98 . ?
C4 H4 0.98 . ?
C5 C4 1.519(3) . ?
C5 C6 1.537(3) . ?
C5 H5 0.98 . ?
C6 C7 1.514(4) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C5 1.539(4) . ?
C8 H8 0.98 . ?
C9 C4 1.524(3) . ?
C9 H9 0.98 . ?
O1 C1 1.197(3) . ?
O2 C7 1.418(4) . ?
O2 C8 1.407(3) . ?
O3 C8 1.417(3) . ?
O3 C9 1.401(3) . ?
O4 C10 1.403(3) . ?
O4 C9 1.408(3) . ?
O5 C1 1.343(3) . ?
O5 C10 1.432(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
C1 C2 C3 105.3(2) . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C1 O5 C10 111.32(18) . . ?
C10 C3 C4 104.29(18) . . ?
C10 C3 H3 111 . . ?
C10 O4 C9 110.88(18) . . ?
C2 C3 C10 103.2(2) . . ?
C2 C3 C4 115.7(2) . . ?
C2 C3 H3 111 . . ?
C3 C10 H10 111.1 . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C3 C4 H4 111.6 . . ?
C4 C3 H3 111 . . ?
C4 C5 C6 116.0(2) . . ?
C4 C5 C8 104.1(2) . . ?
C4 C5 H5 111.1 . . ?
C4 C9 H9 111.1 . . ?
C5 C4 C3 114.6(2) . . ?
C5 C4 C9 104.05(19) . . ?
C5 C4 H4 111.6 . . ?
C5 C6 H6A 111 . . ?
C5 C6 H6B 111 . . ?
C5 C8 H8 110.5 . . ?
C6 C5 C8 102.9(2) . . ?
C6 C5 H5 111.1 . . ?
C6 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
C7 C6 C5 103.6(2) . . ?
C7 C6 H6A 111 . . ?
C7 C6 H6B 111 . . ?
C8 C5 H5 111.1 . . ?
C8 O2 C7 106.5(2) . . ?
C9 C4 C3 102.87(18) . . ?
C9 C4 H4 111.6 . . ?
C9 O3 C8 112.02(17) . . ?
H2A C2 H2B 108.8 . . ?
H6A C6 H6B 109 . . ?
H7A C7 H7B 108.9 . . ?
O1 C1 C2 129.3(3) . . ?
O1 C1 O5 120.2(3) . . ?
O2 C7 C6 104.6(2) . . ?
O2 C7 H7A 110.8 . . ?
O2 C7 H7B 110.8 . . ?
O2 C8 C5 107.4(2) . . ?
O2 C8 H8 110.5 . . ?
O2 C8 O3 110.8(2) . . ?
O3 C8 C5 106.9(2) . . ?
O3 C8 H8 110.5 . . ?
O3 C9 C4 106.36(18) . . ?
O3 C9 H9 111.1 . . ?
O3 C9 O4 108.9(2) . . ?
O4 C10 C3 108.63(19) . . ?
O4 C10 H10 111.1 . . ?
O4 C10 O5 107.7(2) . . ?
O4 C9 C4 108.18(17) . . ?
O4 C9 H9 111.1 . . ?
O5 C1 C2 110.5(2) . . ?
O5 C10 C3 107.1(2) . . ?
O5 C10 H10 111.1 . . ?

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
C1 O5 C10 C3 -12.7(3) . . . . ?
C1 O5 C10 O4 -129.3(2) . . . . ?
C10 C3 C2 C1 -13.8(2) . . . . ?
C10 C3 C4 C5 -132.0(2) . . . . ?
C10 C3 C4 C9 -19.8(3) . . . . ?
C10 O4 C9 C4 -17.1(3) . . . . ?
C10 O4 C9 O3 98.1(2) . . . . ?
C10 O5 C1 C2 3.4(3) . . . . ?
C10 O5 C1 O1 -175.6(2) . . . . ?
C2 C3 C10 O4 132.2(2) . . . . ?
C2 C3 C10 O5 16.1(2) . . . . ?
C2 C3 C4 C5 115.4(3) . . . . ?
C2 C3 C4 C9 -132.4(2) . . . . ?
C3 C2 C1 O1 -174.0(3) . . . . ?
C3 C2 C1 O5 7.2(3) . . . . ?
C4 C3 C10 O4 10.9(3) . . . . ?
C4 C3 C10 O5 -105.2(2) . . . . ?
C4 C3 C2 C1 99.4(2) . . . . ?
C4 C5 C6 C7 -99.4(3) . . . . ?
C5 C6 C7 O2 -32.5(3) . . . . ?
C6 C5 C4 C3 -158.8(2) . . . . ?
C6 C5 C4 C9 89.6(3) . . . . ?
C7 O2 C8 C5 -31.3(3) . . . . ?
C7 O2 C8 O3 85.2(3) . . . . ?
C8 C5 C4 C3 89.0(2) . . . . ?
C8 C5 C4 C9 -22.6(2) . . . . ?
C8 C5 C6 C7 13.6(3) . . . . ?
C8 O2 C7 C6 40.2(3) . . . . ?
C8 O3 C9 C4 -19.1(3) . . . . ?
C8 O3 C9 O4 -135.5(2) . . . . ?
C9 O3 C8 C5 4.3(3) . . . . ?
C9 O3 C8 O2 -112.5(2) . . . . ?
C9 O4 C10 C3 3.7(3) . . . . ?
C9 O4 C10 O5 119.3(2) . . . . ?
O2 C8 C5 C4 131.1(2) . . . . ?
O2 C8 C5 C6 9.7(3) . . . . ?
O3 C8 C5 C4 12.2(3) . . . . ?
O3 C8 C5 C6 -109.2(3) . . . . ?
O3 C9 C4 C3 -94.0(2) . . . . ?
O3 C9 C4 C5 25.8(2) . . . . ?
O4 C9 C4 C3 22.9(2) . . . . ?
O4 C9 C4 C5 142.73(19) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tetracyclic_oligoacetal_4_cif
_database_code_depnum_ccdc_archive 'CCDC 1412443'
_audit_update_record             
;
2015-07-12 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_audit_creation_date             2015-07-12T22:16:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        (1r,2R,6S,8r,10R,14S)-5,7,9,11-
        tetraoxatetracyclo[6.6.0.0^2,6^.0^10,14^]tetradecane
;
_chemical_formula_moiety         'C10 H14 O4'
_chemical_formula_sum            'C10 H14 O4'
_chemical_formula_weight         198.21
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,-z
1/2+x,1/2+y,z
1/2-x,1/2+y,-z

_cell_length_a                   10.420(5)
_cell_length_b                   5.899(3)
_cell_length_c                   15.377(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.096(7)
_cell_angle_gamma                90
_cell_volume                     942.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2178
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.85
_cell_special_details            
;
;

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             424
_exptl_special_details           
;
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.8463
_exptl_absorpt_correction_T_max  0.9957

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoKa
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_number            3444
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             967
_reflns_number_gt                878
_reflns_threshold_expression     I>2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'PLATON (Spek, 2003) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger. Due to the absence of any
 significant anomalous scatterers (Z>Si), attempts to confirm the absolute
 structure by refinement of the Flack parameter led to an inconclusive value
 of -1(4). Therefore the intensities of the Friedel pairs were averaged
 prior to merging of data in C2 and the absolute configuration was assigned
 arbitarily. The reported value of Rint corresponds to subsequent merging
 of equivalent reflections in this space group.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1020P)²+0.5510P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         967
_refine_ls_number_parameters     127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.1933
_refine_ls_wR_factor_gt          0.1887
_refine_ls_goodness_of_fit_ref   1.283
_refine_ls_restrained_S_all      1.282
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_abs_structure_details 'see text above'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.7334(3) 1.1379(8) 0.6018(3) 0.0646(13) Uani 1 1 d . . .
O2 O 0.8382(3) 0.9158(7) 0.7092(3) 0.0562(11) Uani 1 1 d . . .
O3 O 1.0154(4) 0.8033(8) 0.7971(3) 0.0614(12) Uani 1 1 d . . .
O4 O 1.1356(5) 0.9147(9) 0.9210(3) 0.0815(16) Uani 1 1 d . . .
C1 C 0.8382(6) 1.2012(14) 0.5514(4) 0.0683(18) Uani 1 1 d . . .
H1A H 0.8068 1.2639 0.4956 0.082 Uiso 1 1 calc R . .
H1B H 0.8925 1.0716 0.5414 0.082 Uiso 1 1 calc R . .
C2 C 0.9100(6) 1.3752(12) 0.6055(4) 0.0659(18) Uani 1 1 d . . .
H2A H 0.876 1.5255 0.5927 0.079 Uiso 1 1 calc R . .
H2B H 1.0007 1.3733 0.5949 0.079 Uiso 1 1 calc R . .
C3 C 0.8904(5) 1.3090(10) 0.6988(4) 0.0480(13) Uani 1 1 d . . .
H3 H 0.8633 1.4395 0.7324 0.058 Uiso 1 1 calc R . .
C4 C 1.0002(4) 1.1794(9) 0.7485(3) 0.0402(11) Uani 1 1 d . . .
H4 H 1.084 1.229 0.7303 0.048 Uiso 1 1 calc R . .
C5 C 0.9984(5) 1.1820(10) 0.8461(4) 0.0490(13) Uani 1 1 d . . .
H5 H 0.9164 1.241 0.8641 0.059 Uiso 1 1 calc R . .
C6 C 1.1120(6) 1.3000(11) 0.8955(4) 0.0593(16) Uani 1 1 d . . .
H6A H 1.1443 1.4239 0.8618 0.071 Uiso 1 1 calc R . .
H6B H 1.0887 1.3571 0.9514 0.071 Uiso 1 1 calc R . .
C7 C 1.2083(5) 1.1119(12) 0.9066(4) 0.0636(17) Uani 1 1 d . . .
H7A H 1.2552 1.0954 0.8547 0.076 Uiso 1 1 calc R . .
H7B H 1.2693 1.1413 0.956 0.076 Uiso 1 1 calc R . .
C8 C 1.0171(6) 0.9320(12) 0.8737(4) 0.0585(16) Uani 1 1 d . . .
H8 H 0.9478 0.8837 0.9093 0.07 Uiso 1 1 calc R . .
C9 C 0.9752(4) 0.9332(10) 0.7245(3) 0.0450(12) Uani 1 1 d . . .
H9 H 1.0195 0.889 0.673 0.054 Uiso 1 1 calc R . .
C10 C 0.7818(5) 1.1290(10) 0.6877(4) 0.0489(13) Uani 1 1 d . . .
H10 H 0.7139 1.1631 0.7266 0.059 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C10 1.381(7) . ?
O1 C1 1.433(7) . ?
O2 C10 1.417(7) . ?
O2 C9 1.434(6) . ?
O3 C9 1.393(7) . ?
O3 C8 1.400(8) . ?
O4 C8 1.392(7) . ?
O4 C7 1.414(8) . ?
C1 C2 1.488(9) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 C3 1.514(9) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.534(7) . ?
C3 C10 1.552(8) . ?
C3 H3 0.98 . ?
C4 C5 1.503(8) . ?
C4 C9 1.516(8) . ?
C4 H4 0.98 . ?
C5 C6 1.528(8) . ?
C5 C8 1.542(10) . ?
C5 H5 0.98 . ?
C6 C7 1.497(9) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 H8 0.98 . ?
C9 H9 0.98 . ?
C10 H10 0.98 . ?

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
C10 O1 C1 106.7(4) . . ?
C10 O2 C9 111.5(4) . . ?
C9 O3 C8 111.1(5) . . ?
C8 O4 C7 108.8(5) . . ?
O1 C1 C2 104.4(5) . . ?
O1 C1 H1A 110.9 . . ?
C2 C1 H1A 110.9 . . ?
O1 C1 H1B 110.9 . . ?
C2 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
C1 C2 C3 104.8(5) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 117.0(5) . . ?
C2 C3 C10 102.7(4) . . ?
C4 C3 C10 103.1(4) . . ?
C2 C3 H3 111.1 . . ?
C4 C3 H3 111.1 . . ?
C10 C3 H3 111.1 . . ?
C5 C4 C9 103.8(5) . . ?
C5 C4 C3 115.5(4) . . ?
C9 C4 C3 104.3(4) . . ?
C5 C4 H4 110.9 . . ?
C9 C4 H4 110.9 . . ?
C3 C4 H4 110.9 . . ?
C4 C5 C6 115.9(5) . . ?
C4 C5 C8 104.7(5) . . ?
C6 C5 C8 102.8(5) . . ?
C4 C5 H5 111 . . ?
C6 C5 H5 111 . . ?
C8 C5 H5 111 . . ?
C7 C6 C5 102.0(5) . . ?
C7 C6 H6A 111.4 . . ?
C5 C6 H6A 111.4 . . ?
C7 C6 H6B 111.4 . . ?
C5 C6 H6B 111.4 . . ?
H6A C6 H6B 109.2 . . ?
O4 C7 C6 105.4(5) . . ?
O4 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
O4 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
O4 C8 O3 110.9(6) . . ?
O4 C8 C5 107.7(5) . . ?
O3 C8 C5 107.1(5) . . ?
O4 C8 H8 110.4 . . ?
O3 C8 H8 110.4 . . ?
C5 C8 H8 110.4 . . ?
O3 C9 O2 109.3(4) . . ?
O3 C9 C4 107.2(4) . . ?
O2 C9 C4 105.1(4) . . ?
O3 C9 H9 111.6 . . ?
O2 C9 H9 111.6 . . ?
C4 C9 H9 111.6 . . ?
O1 C10 O2 112.0(5) . . ?
O1 C10 C3 107.0(4) . . ?
O2 C10 C3 107.2(4) . . ?
O1 C10 H10 110.2 . . ?
O2 C10 H10 110.2 . . ?
C3 C10 H10 110.2 . . ?

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
C10 O1 C1 C2 -39.6(6) . . . . ?
O1 C1 C2 C3 31.0(7) . . . . ?
C1 C2 C3 C4 99.8(6) . . . . ?
C1 C2 C3 C10 -12.2(6) . . . . ?
C2 C3 C4 C5 161.0(5) . . . . ?
C10 C3 C4 C5 -87.3(5) . . . . ?
C2 C3 C4 C9 -85.8(6) . . . . ?
C10 C3 C4 C9 25.9(5) . . . . ?
C9 C4 C5 C6 130.4(5) . . . . ?
C3 C4 C5 C6 -116.1(6) . . . . ?
C9 C4 C5 C8 18.0(5) . . . . ?
C3 C4 C5 C8 131.5(5) . . . . ?
C4 C5 C6 C7 -87.4(6) . . . . ?
C8 C5 C6 C7 26.2(6) . . . . ?
C8 O4 C7 C6 33.4(7) . . . . ?
C5 C6 C7 O4 -36.6(6) . . . . ?
C7 O4 C8 O3 101.3(7) . . . . ?
C7 O4 C8 C5 -15.6(7) . . . . ?
C9 O3 C8 O4 -127.9(5) . . . . ?
C9 O3 C8 C5 -10.7(6) . . . . ?
C4 C5 C8 O4 113.7(5) . . . . ?
C6 C5 C8 O4 -7.8(7) . . . . ?
C4 C5 C8 O3 -5.7(6) . . . . ?
C6 C5 C8 O3 -127.1(5) . . . . ?
C8 O3 C9 O2 -90.7(5) . . . . ?
C8 O3 C9 C4 22.8(5) . . . . ?
C10 O2 C9 O3 137.7(5) . . . . ?
C10 O2 C9 C4 22.9(6) . . . . ?
C5 C4 C9 O3 -25.1(5) . . . . ?
C3 C4 C9 O3 -146.4(4) . . . . ?
C5 C4 C9 O2 91.2(4) . . . . ?
C3 C4 C9 O2 -30.1(5) . . . . ?
C1 O1 C10 O2 -85.5(6) . . . . ?
C1 O1 C10 C3 31.6(6) . . . . ?
C9 O2 C10 O1 111.0(5) . . . . ?
C9 O2 C10 C3 -6.0(6) . . . . ?
C2 C3 C10 O1 -11.3(6) . . . . ?
C4 C3 C10 O1 -133.2(4) . . . . ?
C2 C3 C10 O2 109.0(5) . . . . ?
C4 C3 C10 O2 -13.0(5) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
