# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_fr06d
_database_code_depnum_ccdc_archive 'CCDC 1032856'
_audit_update_record             
;
2014-11-05 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"(4aS,6aS,6bR,9aR,10aR,10bR)-8,8-Dimethyl-4,4a,6b,9a,10a,10b-hexahydro-3H-[1,3]dioxolo [4',5':4,5] furo[3,2-c]isochromen-5(6aH)-one"
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 O5'
_chemical_formula_weight         266.28

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.7984(9)
_cell_length_b                   9.8986(14)
_cell_length_c                   18.713(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1259.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3733
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.92

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_T_max  0.9915

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7590
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         28.24
_reflns_number_total             2900
_reflns_number_gt                2800
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_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 > 2sigma(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)+(0.0398P)²+0.6060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_number_reflns         2900
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0950(2) 0.61159(16) 0.74357(9) 0.0284(4) Uani 1 d . . .
O2 O 0.1900(2) 0.51682(15) 0.75988(8) 0.0210(3) Uani 1 d . . .
O3 O 0.2960(2) 0.51772(14) 0.91261(7) 0.0164(3) Uani 1 d . . .
O4 O 0.5288(2) 0.35320(14) 0.93764(7) 0.0157(3) Uani 1 d . . .
O5 O 0.5908(2) 0.31426(15) 0.82046(7) 0.0176(3) Uani 1 d . . .
C1 C 0.3288(3) 0.7337(2) 0.85039(11) 0.0173(4) Uani 1 d . . .
H1 H 0.4138 0.7777 0.8151 0.021 Uiso 1 calc R . .
C2 C 0.3496(3) 0.8136(2) 0.91864(11) 0.0205(4) Uani 1 d . . .
H2 H 0.4721 0.8144 0.9408 0.025 Uiso 1 calc R . .
C3 C 0.2051(4) 0.8827(2) 0.94922(12) 0.0225(5) Uani 1 d . . .
H3 H 0.2331 0.9334 0.9898 0.027 Uiso 1 calc R . .
C4 C -0.0007(4) 0.8825(2) 0.92117(12) 0.0248(5) Uani 1 d . . .
H4A H -0.0212 0.9619 0.8917 0.030 Uiso 1 calc R . .
H4B H -0.0924 0.8865 0.9608 0.030 Uiso 1 calc R . .
C5 C -0.0404(3) 0.7560(2) 0.87714(12) 0.0215(5) Uani 1 d . . .
H5A H -0.1684 0.7630 0.8546 0.026 Uiso 1 calc R . .
H5B H -0.0415 0.6776 0.9082 0.026 Uiso 1 calc R . .
C6 C 0.1182(3) 0.7383(2) 0.81970(11) 0.0173(4) Uani 1 d . . .
H6 H 0.1118 0.8189 0.7894 0.021 Uiso 1 calc R . .
C7 C 0.0629(3) 0.6193(2) 0.77216(11) 0.0203(4) Uani 1 d . . .
C8 C 0.3822(3) 0.5048(2) 0.79288(10) 0.0166(4) Uani 1 d . . .
H8 H 0.4879 0.5217 0.7584 0.020 Uiso 1 calc R . .
C9 C 0.4052(3) 0.5914(2) 0.85886(10) 0.0159(4) Uani 1 d . . .
H9 H 0.5443 0.5946 0.8725 0.019 Uiso 1 calc R . .
C10 C 0.3471(3) 0.3819(2) 0.90320(10) 0.0152(4) Uani 1 d . . .
H10 H 0.2423 0.3214 0.9196 0.018 Uiso 1 calc R . .
C11 C 0.3926(3) 0.3610(2) 0.82291(11) 0.0159(4) Uani 1 d . . .
H11 H 0.3003 0.2990 0.7996 0.019 Uiso 1 calc R . .
C12 C 0.6403(3) 0.2684(2) 0.89085(11) 0.0164(4) Uani 1 d . . .
C13 C 0.5807(3) 0.1218(2) 0.90047(11) 0.0209(4) Uani 1 d . . .
H13A H 0.4430 0.1121 0.8904 0.031 Uiso 1 calc R . .
H13B H 0.6064 0.0944 0.9488 0.031 Uiso 1 calc R . .
H13C H 0.6551 0.0662 0.8683 0.031 Uiso 1 calc R . .
C14 C 0.8564(3) 0.2941(2) 0.90283(11) 0.0203(4) Uani 1 d . . .
H14A H 0.8913 0.2679 0.9506 0.031 Uiso 1 calc R . .
H14B H 0.8836 0.3885 0.8963 0.031 Uiso 1 calc R . .
H14C H 0.9319 0.2424 0.8692 0.031 Uiso 1 calc R . .


_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 1.202(3) . ?
O2 C7 1.352(3) . ?
O2 C8 1.450(2) . ?
O3 C10 1.400(2) . ?
O3 C9 1.447(2) . ?
O4 C10 1.422(2) . ?
O4 C12 1.430(2) . ?
O5 C11 1.425(2) . ?
O5 C12 1.433(2) . ?
C1 C2 1.509(3) . ?
C1 C9 1.509(3) . ?
C1 C6 1.543(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.327(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.494(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.523(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.533(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.523(3) . ?
C6 H6 0.9800 . ?
C8 C9 1.511(3) . ?
C8 C11 1.533(3) . ?
C8 H8 0.9800 . ?
C9 H9 0.9800 . ?
C10 C11 1.548(3) . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C12 C14 1.508(3) . ?
C12 C13 1.517(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 O2 C8 124.38(16) . . ?
C10 O3 C9 105.64(14) . . ?
C10 O4 C12 107.45(15) . . ?
C11 O5 C12 107.15(15) . . ?
C2 C1 C9 111.57(17) . . ?
C2 C1 C6 112.75(18) . . ?
C9 C1 C6 112.69(17) . . ?
C2 C1 H1 106.4 . . ?
C9 C1 H1 106.4 . . ?
C6 C1 H1 106.4 . . ?
C3 C2 C1 124.5(2) . . ?
C3 C2 H2 117.8 . . ?
C1 C2 H2 117.8 . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 110.90(19) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 110.42(18) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 108.94(18) . . ?
C7 C6 C1 115.06(17) . . ?
C5 C6 C1 113.25(17) . . ?
C7 C6 H6 106.3 . . ?
C5 C6 H6 106.3 . . ?
C1 C6 H6 106.3 . . ?
O1 C7 O2 116.6(2) . . ?
O1 C7 C6 122.0(2) . . ?
O2 C7 C6 121.46(18) . . ?
O2 C8 C9 113.23(17) . . ?
O2 C8 C11 105.89(17) . . ?
C9 C8 C11 102.88(15) . . ?
O2 C8 H8 111.5 . . ?
C9 C8 H8 111.5 . . ?
C11 C8 H8 111.5 . . ?
O3 C9 C1 111.54(16) . . ?
O3 C9 C8 103.23(16) . . ?
C1 C9 C8 114.08(17) . . ?
O3 C9 H9 109.3 . . ?
C1 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
O3 C10 O4 110.52(15) . . ?
O3 C10 C11 107.49(15) . . ?
O4 C10 C11 103.85(15) . . ?
O3 C10 H10 111.6 . . ?
O4 C10 H10 111.6 . . ?
C11 C10 H10 111.6 . . ?
O5 C11 C8 109.46(17) . . ?
O5 C11 C10 105.29(16) . . ?
C8 C11 C10 102.84(16) . . ?
O5 C11 H11 112.8 . . ?
C8 C11 H11 112.8 . . ?
C10 C11 H11 112.8 . . ?
O4 C12 O5 104.64(15) . . ?
O4 C12 C14 109.02(16) . . ?
O5 C12 C14 108.16(17) . . ?
O4 C12 C13 110.32(16) . . ?
O5 C12 C13 110.45(17) . . ?
C14 C12 C13 113.82(18) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054
_chemical_melting_point          437-439
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_fr06c11
_database_code_depnum_ccdc_archive 'CCDC 1032857'
_audit_update_record             
;
2014-11-05 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(4aR,6aS,6bR,9aR,10aR,10bS)-8,8-dimethyl-4,4a,6b,9a,10a,10b-hexahydro-3H-[1,3]dioxolo[4',5':4,5]furo[3,2-c]isochromen-5(6aH)-one
_chemical_name_common            ?
_chemical_melting_point          449-451
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 O5'
_chemical_formula_weight         266.28

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   7.5121(5)
_cell_length_b                   6.9024(4)
_cell_length_c                   12.6590(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.1140(10)
_cell_angle_gamma                90.00
_cell_volume                     649.82(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7427
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         28.40
_reflns_number_total             2288
_reflns_number_gt                2239
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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)+(0.0410P)²+0.0970P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.055(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_number_reflns         2288
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.02413(12) 1.04830(14) 0.21910(8) 0.0304(2) Uani 1 1 d . . .
O2 O -0.28524(11) 0.69834(17) 0.29442(7) 0.0320(2) Uani 1 1 d . . .
O3 O 0.22690(16) 1.26027(17) 0.19050(12) 0.0461(3) Uani 1 1 d . . .
O4 O 0.15492(11) 0.70058(16) 0.34521(6) 0.0264(2) Uani 1 1 d . . .
O5 O -0.07974(12) 0.54709(17) 0.41372(7) 0.0295(2) Uani 1 1 d . . .
C1 C 0.3527(2) 0.9949(2) -0.00009(11) 0.0342(3) Uani 1 1 d . . .
H9 H 0.2866 1.1159 -0.0089 0.041 Uiso 1 1 calc R . .
H1 H 0.4376 0.9931 -0.0512 0.041 Uiso 1 1 calc R . .
C2 C 0.45569(16) 0.9845(2) 0.11314(11) 0.0291(3) Uani 1 1 d . . .
H10 H 0.5117 1.1088 0.1319 0.035 Uiso 1 1 calc R . .
H11 H 0.5501 0.8881 0.1156 0.035 Uiso 1 1 calc R . .
C3 C 0.32969(15) 0.93168(19) 0.19431(10) 0.0223(2) Uani 1 1 d . . .
H12 H 0.4031 0.9246 0.2646 0.027 Uiso 1 1 calc R . .
C4 C 0.19242(17) 1.0912(2) 0.19917(10) 0.0265(3) Uani 1 1 d . . .
C5 C -0.04832(15) 0.85395(19) 0.21674(10) 0.0226(2) Uani 1 1 d . . .
H13 H -0.1332 0.8323 0.1516 0.027 Uiso 1 1 calc R . .
C6 C -0.14138(17) 0.8322(2) 0.31578(11) 0.0275(3) Uani 1 1 d . . .
H14 H -0.1791 0.9566 0.3427 0.033 Uiso 1 1 calc R . .
C7 C -0.26875(16) 0.5625(2) 0.38097(9) 0.0263(3) Uani 1 1 d . . .
C8 C -0.3389(2) 0.3694(3) 0.33882(12) 0.0395(3) Uani 1 1 d . . .
H2 H -0.3262 0.2765 0.3958 0.059 Uiso 1 1 calc R . .
H16 H -0.2718 0.3271 0.2839 0.059 Uiso 1 1 calc R . .
H15 H -0.4636 0.3815 0.3098 0.059 Uiso 1 1 calc R . .
C9 C -0.3628(2) 0.6376(3) 0.47144(14) 0.0459(4) Uani 1 1 d . . .
H17 H -0.3123 0.7604 0.4953 0.069 Uiso 1 1 calc R . .
H3 H -0.3467 0.5469 0.5295 0.069 Uiso 1 1 calc R . .
H18 H -0.4888 0.6529 0.4467 0.069 Uiso 1 1 calc R . .
C10 C 0.22425(17) 0.8293(2) -0.02263(11) 0.0299(3) Uani 1 1 d . . .
H8 H 0.1716 0.8094 -0.0928 0.036 Uiso 1 1 calc R . .
C11 C 0.18110(16) 0.7091(2) 0.05158(10) 0.0268(3) Uani 1 1 d . . .
H7 H 0.1053 0.6056 0.0299 0.032 Uiso 1 1 calc R . .
C12 C 0.24822(15) 0.73083(18) 0.16961(9) 0.0212(2) Uani 1 1 d . . .
H6 H 0.3410 0.6329 0.1904 0.025 Uiso 1 1 calc R . .
C13 C 0.09301(14) 0.69590(19) 0.23174(9) 0.0196(2) Uani 1 1 d . . .
H5 H 0.0374 0.5702 0.2119 0.023 Uiso 1 1 calc R . .
C14 C 0.00170(16) 0.7278(2) 0.39609(9) 0.0268(3) Uani 1 1 d . . .
H4 H 0.0301 0.8016 0.4625 0.032 Uiso 1 1 calc R . .


_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 C4 1.3563(16) . ?
O1 C5 1.4464(16) . ?
O2 C6 1.4187(17) . ?
O2 C7 1.4339(16) . ?
O3 C4 1.2036(18) . ?
O4 C14 1.4086(15) . ?
O4 C13 1.4464(13) . ?
O5 C14 1.4211(18) . ?
O5 C7 1.4259(14) . ?
C1 C10 1.497(2) . ?
C1 C2 1.5315(19) . ?
C1 H9 0.9700 . ?
C1 H1 0.9700 . ?
C2 C3 1.5361(17) . ?
C2 H10 0.9700 . ?
C2 H11 0.9700 . ?
C3 C4 1.5158(18) . ?
C3 C12 1.5298(17) . ?
C3 H12 0.9800 . ?
C5 C13 1.5153(16) . ?
C5 C6 1.5267(17) . ?
C5 H13 0.9800 . ?
C6 C14 1.5490(18) . ?
C6 H14 0.9800 . ?
C7 C8 1.503(2) . ?
C7 C9 1.519(2) . ?
C8 H2 0.9600 . ?
C8 H16 0.9600 . ?
C8 H15 0.9600 . ?
C9 H17 0.9600 . ?
C9 H3 0.9600 . ?
C9 H18 0.9600 . ?
C10 C11 1.327(2) . ?
C10 H8 0.9300 . ?
C11 C12 1.5154(16) . ?
C11 H7 0.9300 . ?
C12 C13 1.5150(15) . ?
C12 H6 0.9800 . ?
C13 H5 0.9800 . ?
C14 H4 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C5 123.83(10) . . ?
C6 O2 C7 107.39(10) . . ?
C14 O4 C13 106.74(8) . . ?
C14 O5 C7 108.77(10) . . ?
C10 C1 C2 111.70(12) . . ?
C10 C1 H9 109.3 . . ?
C2 C1 H9 109.3 . . ?
C10 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
H9 C1 H1 107.9 . . ?
C1 C2 C3 111.07(10) . . ?
C1 C2 H10 109.4 . . ?
C3 C2 H10 109.4 . . ?
C1 C2 H11 109.4 . . ?
C3 C2 H11 109.4 . . ?
H10 C2 H11 108.0 . . ?
C4 C3 C12 114.32(10) . . ?
C4 C3 C2 109.98(11) . . ?
C12 C3 C2 110.17(10) . . ?
C4 C3 H12 107.4 . . ?
C12 C3 H12 107.4 . . ?
C2 C3 H12 107.4 . . ?
O3 C4 O1 116.55(13) . . ?
O3 C4 C3 122.97(12) . . ?
O1 C4 C3 120.40(12) . . ?
O1 C5 C13 114.21(9) . . ?
O1 C5 C6 106.78(10) . . ?
C13 C5 C6 102.73(10) . . ?
O1 C5 H13 110.9 . . ?
C13 C5 H13 110.9 . . ?
C6 C5 H13 110.9 . . ?
O2 C6 C5 109.40(11) . . ?
O2 C6 C14 105.15(11) . . ?
C5 C6 C14 103.23(10) . . ?
O2 C6 H14 112.8 . . ?
C5 C6 H14 112.8 . . ?
C14 C6 H14 112.8 . . ?
O5 C7 O2 104.25(9) . . ?
O5 C7 C8 108.78(12) . . ?
O2 C7 C8 108.68(11) . . ?
O5 C7 C9 110.87(12) . . ?
O2 C7 C9 110.73(13) . . ?
C8 C7 C9 113.14(12) . . ?
C7 C8 H2 109.5 . . ?
C7 C8 H16 109.5 . . ?
H2 C8 H16 109.5 . . ?
C7 C8 H15 109.5 . . ?
H2 C8 H15 109.5 . . ?
H16 C8 H15 109.5 . . ?
C7 C9 H17 109.5 . . ?
C7 C9 H3 109.5 . . ?
H17 C9 H3 109.5 . . ?
C7 C9 H18 109.5 . . ?
H17 C9 H18 109.5 . . ?
H3 C9 H18 109.5 . . ?
C11 C10 C1 123.88(12) . . ?
C11 C10 H8 118.1 . . ?
C1 C10 H8 118.1 . . ?
C10 C11 C12 123.74(12) . . ?
C10 C11 H7 118.1 . . ?
C12 C11 H7 118.1 . . ?
C13 C12 C11 108.83(9) . . ?
C13 C12 C3 110.67(10) . . ?
C11 C12 C3 111.05(10) . . ?
C13 C12 H6 108.7 . . ?
C11 C12 H6 108.7 . . ?
C3 C12 H6 108.7 . . ?
O4 C13 C12 110.42(8) . . ?
O4 C13 C5 103.28(10) . . ?
C12 C13 C5 113.41(10) . . ?
O4 C13 H5 109.8 . . ?
C12 C13 H5 109.8 . . ?
C5 C13 H5 109.8 . . ?
O4 C14 O5 110.62(12) . . ?
O4 C14 C6 107.35(10) . . ?
O5 C14 C6 103.72(10) . . ?
O4 C14 H4 111.6 . . ?
O5 C14 H4 111.6 . . ?
C6 C14 H4 111.6 . . ?

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
C10 C1 C2 C3 -43.59(17) . . . . ?
C1 C2 C3 C4 -64.65(15) . . . . ?
C1 C2 C3 C12 62.26(14) . . . . ?
C5 O1 C4 O3 170.82(14) . . . . ?
C5 O1 C4 C3 -12.25(17) . . . . ?
C12 C3 C4 O3 -160.53(14) . . . . ?
C2 C3 C4 O3 -35.99(19) . . . . ?
C12 C3 C4 O1 22.74(16) . . . . ?
C2 C3 C4 O1 147.28(11) . . . . ?
C4 O1 C5 C13 21.97(16) . . . . ?
C4 O1 C5 C6 134.79(12) . . . . ?
C7 O2 C6 C5 131.14(11) . . . . ?
C7 O2 C6 C14 20.85(13) . . . . ?
O1 C5 C6 O2 150.57(10) . . . . ?
C13 C5 C6 O2 -88.94(12) . . . . ?
O1 C5 C6 C14 -97.87(11) . . . . ?
C13 C5 C6 C14 22.61(13) . . . . ?
C14 O5 C7 O2 31.73(13) . . . . ?
C14 O5 C7 C8 147.54(11) . . . . ?
C14 O5 C7 C9 -87.45(13) . . . . ?
C6 O2 C7 O5 -32.42(13) . . . . ?
C6 O2 C7 C8 -148.30(11) . . . . ?
C6 O2 C7 C9 86.86(14) . . . . ?
C2 C1 C10 C11 11.4(2) . . . . ?
C1 C10 C11 C12 3.6(2) . . . . ?
C10 C11 C12 C13 136.45(13) . . . . ?
C10 C11 C12 C3 14.38(17) . . . . ?
C4 C3 C12 C13 -42.49(13) . . . . ?
C2 C3 C12 C13 -166.93(10) . . . . ?
C4 C3 C12 C11 78.50(13) . . . . ?
C2 C3 C12 C11 -45.94(13) . . . . ?
C14 O4 C13 C12 162.11(11) . . . . ?
C14 O4 C13 C5 40.54(13) . . . . ?
C11 C12 C13 O4 175.56(11) . . . . ?
C3 C12 C13 O4 -62.14(12) . . . . ?
C11 C12 C13 C5 -69.07(13) . . . . ?
C3 C12 C13 C5 53.22(13) . . . . ?
O1 C5 C13 O4 76.79(12) . . . . ?
C6 C5 C13 O4 -38.42(12) . . . . ?
O1 C5 C13 C12 -42.73(14) . . . . ?
C6 C5 C13 C12 -157.95(10) . . . . ?
C13 O4 C14 O5 86.78(11) . . . . ?
C13 O4 C14 C6 -25.75(14) . . . . ?
C7 O5 C14 O4 -133.33(10) . . . . ?
C7 O5 C14 C6 -18.51(12) . . . . ?
O2 C6 C14 O4 115.56(11) . . . . ?
C5 C6 C14 O4 0.90(15) . . . . ?
O2 C6 C14 O5 -1.58(13) . . . . ?
C5 C6 C14 O5 -116.23(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.031
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_fr06c21
_database_code_depnum_ccdc_archive 'CCDC 1032858'
_audit_update_record             
;
2014-11-05 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"(4aS,6aS,6bR,9aR,10aR,10bS)-8,8-dimethyl-4,4a,6b,9a,10a,10b-hexahydro-3H-[1,3]dioxolo [4',5':4,5]furo[3,2-c]isochromen-5(6aH)-one"
_chemical_name_common            ?
_chemical_melting_point          435-437
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 O5'
_chemical_formula_weight         266.28

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.4993(2)
_cell_length_b                   10.9036(4)
_cell_length_c                   18.6419(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1321.07(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9669
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17701
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         28.27
_reflns_number_total             3273
_reflns_number_gt                3103
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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)+(0.0446P)²+0.1715P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0053(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_number_reflns         3273
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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 0.44394(15) 1.14566(7) 0.82183(4) 0.0311(2) Uani 1 1 d . . .
O2 O 0.54015(15) 0.94323(8) 0.80084(4) 0.0320(2) Uani 1 1 d . . .
O3 O 0.51809(16) 1.12381(7) 0.93897(5) 0.0357(2) Uani 1 1 d . . .
O4 O 0.51886(13) 0.79800(7) 0.94214(4) 0.02896(19) Uani 1 1 d . . .
O5 O 0.57124(15) 0.60209(8) 0.96270(5) 0.0339(2) Uani 1 1 d . . .
C1 C 0.2289(3) 1.25299(16) 0.90713(9) 0.0535(4) Uani 1 1 d . . .
H1 H 0.1405 1.1827 0.9107 0.080 Uiso 1 1 calc R . .
H8 H 0.1781 1.3070 0.8705 0.080 Uiso 1 1 calc R . .
H7 H 0.2313 1.2954 0.9522 0.080 Uiso 1 1 calc R . .
C2 C 0.4453(2) 1.21158(11) 0.88799(6) 0.0319(3) Uani 1 1 d . . .
C3 C 0.40253(19) 1.02096(10) 0.83638(6) 0.0276(2) Uani 1 1 d . . .
H12 H 0.2599 1.0003 0.8243 0.033 Uiso 1 1 calc R . .
C4 C 0.70744(18) 0.91211(10) 0.84820(5) 0.0241(2) Uani 1 1 d . . .
H13 H 0.8163 0.9740 0.8447 0.029 Uiso 1 1 calc R . .
C5 C 0.79179(17) 0.78640(10) 0.82720(6) 0.0240(2) Uani 1 1 d . . .
H14 H 0.6863 0.7442 0.7989 0.029 Uiso 1 1 calc R . .
C6 C 0.83293(17) 0.70969(10) 0.89497(6) 0.0244(2) Uani 1 1 d . . .
H15 H 0.9299 0.7553 0.9251 0.029 Uiso 1 1 calc R . .
C7 C 0.93245(19) 0.58739(11) 0.87549(7) 0.0308(2) Uani 1 1 d . . .
H16 H 0.8460 0.5437 0.8416 0.037 Uiso 1 1 calc R . .
H17 H 0.9470 0.5372 0.9182 0.037 Uiso 1 1 calc R . .
C8 C 1.1436(2) 0.61057(13) 0.84229(8) 0.0372(3) Uani 1 1 d . . .
H2 H 1.2415 0.6283 0.8802 0.045 Uiso 1 1 calc R . .
H18 H 1.1892 0.5369 0.8178 0.045 Uiso 1 1 calc R . .
C9 C 0.9854(2) 0.79236(13) 0.78275(7) 0.0340(3) Uani 1 1 d . . .
H4 H 0.9960 0.8537 0.7483 0.041 Uiso 1 1 calc R . .
C10 C 1.1413(2) 0.71501(13) 0.79011(8) 0.0377(3) Uani 1 1 d . . .
H3 H 1.2562 0.7263 0.7611 0.045 Uiso 1 1 calc R . .
C11 C 0.4412(2) 1.00757(10) 0.91778(6) 0.0281(2) Uani 1 1 d . . .
H6 H 0.3176 0.9833 0.9444 0.034 Uiso 1 1 calc R . .
C12 C 0.61347(19) 0.91400(10) 0.92334(6) 0.0252(2) Uani 1 1 d . . .
H5 H 0.7154 0.9387 0.9593 0.030 Uiso 1 1 calc R . .
C13 C 0.63546(18) 0.69528(10) 0.93632(6) 0.0257(2) Uani 1 1 d . . .
C14 C 0.5969(3) 1.31478(13) 0.88230(9) 0.0505(4) Uani 1 1 d . . .
H9 H 0.5598 1.3669 0.8428 0.076 Uiso 1 1 calc R . .
H11 H 0.7321 1.2820 0.8745 0.076 Uiso 1 1 calc R . .
H10 H 0.5957 1.3615 0.9259 0.076 Uiso 1 1 calc R . .


_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 C3 1.4124(14) . ?
O1 C2 1.4276(14) . ?
O2 C3 1.3990(14) . ?
O2 C4 1.4412(14) . ?
O3 C11 1.4185(15) . ?
O3 C2 1.4293(14) . ?
O4 C13 1.3567(14) . ?
O4 C12 1.4493(14) . ?
O5 C13 1.2035(14) . ?
C1 C2 1.520(2) . ?
C1 H1 0.9600 . ?
C1 H8 0.9600 . ?
C1 H7 0.9600 . ?
C2 C14 1.499(2) . ?
C3 C11 1.5450(15) . ?
C3 H12 0.9800 . ?
C4 C5 1.5273(15) . ?
C4 C12 1.5282(15) . ?
C4 H13 0.9800 . ?
C5 C9 1.5081(16) . ?
C5 C6 1.5385(15) . ?
C5 H14 0.9800 . ?
C6 C13 1.5054(16) . ?
C6 C7 1.5260(15) . ?
C6 H15 0.9800 . ?
C7 C8 1.5265(18) . ?
C7 H16 0.9700 . ?
C7 H17 0.9700 . ?
C8 C10 1.498(2) . ?
C8 H2 0.9700 . ?
C8 H18 0.9700 . ?
C9 C10 1.3253(19) . ?
C9 H4 0.9300 . ?
C10 H3 0.9300 . ?
C11 C12 1.5184(17) . ?
C11 H6 0.9800 . ?
C12 H5 0.9800 . ?
C14 H9 0.9600 . ?
C14 H11 0.9600 . ?
C14 H10 0.9600 . ?

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
C3 O1 C2 108.66(8) . . ?
C3 O2 C4 109.56(8) . . ?
C11 O3 C2 107.24(9) . . ?
C13 O4 C12 117.65(9) . . ?
C2 C1 H1 109.5 . . ?
C2 C1 H8 109.5 . . ?
H1 C1 H8 109.5 . . ?
C2 C1 H7 109.5 . . ?
H1 C1 H7 109.5 . . ?
H8 C1 H7 109.5 . . ?
O1 C2 O3 103.85(9) . . ?
O1 C2 C14 108.71(11) . . ?
O3 C2 C14 109.39(12) . . ?
O1 C2 C1 110.29(13) . . ?
O3 C2 C1 110.45(11) . . ?
C14 C2 C1 113.69(12) . . ?
O2 C3 O1 111.74(10) . . ?
O2 C3 C11 107.69(9) . . ?
O1 C3 C11 104.39(9) . . ?
O2 C3 H12 110.9 . . ?
O1 C3 H12 110.9 . . ?
C11 C3 H12 110.9 . . ?
O2 C4 C5 108.97(9) . . ?
O2 C4 C12 104.89(9) . . ?
C5 C4 C12 112.99(9) . . ?
O2 C4 H13 110.0 . . ?
C5 C4 H13 110.0 . . ?
C12 C4 H13 110.0 . . ?
C9 C5 C4 113.68(10) . . ?
C9 C5 C6 109.24(9) . . ?
C4 C5 C6 109.86(8) . . ?
C9 C5 H14 108.0 . . ?
C4 C5 H14 108.0 . . ?
C6 C5 H14 108.0 . . ?
C13 C6 C7 113.08(9) . . ?
C13 C6 C5 109.22(9) . . ?
C7 C6 C5 110.69(9) . . ?
C13 C6 H15 107.9 . . ?
C7 C6 H15 107.9 . . ?
C5 C6 H15 107.9 . . ?
C6 C7 C8 109.44(10) . . ?
C6 C7 H16 109.8 . . ?
C8 C7 H16 109.8 . . ?
C6 C7 H17 109.8 . . ?
C8 C7 H17 109.8 . . ?
H16 C7 H17 108.2 . . ?
C10 C8 C7 112.34(10) . . ?
C10 C8 H2 109.1 . . ?
C7 C8 H2 109.1 . . ?
C10 C8 H18 109.1 . . ?
C7 C8 H18 109.1 . . ?
H2 C8 H18 107.9 . . ?
C10 C9 C5 123.61(12) . . ?
C10 C9 H4 118.2 . . ?
C5 C9 H4 118.2 . . ?
C9 C10 C8 123.97(12) . . ?
C9 C10 H3 118.0 . . ?
C8 C10 H3 118.0 . . ?
O3 C11 C12 108.75(10) . . ?
O3 C11 C3 104.26(9) . . ?
C12 C11 C3 104.51(9) . . ?
O3 C11 H6 112.9 . . ?
C12 C11 H6 112.9 . . ?
C3 C11 H6 112.9 . . ?
O4 C12 C11 106.86(10) . . ?
O4 C12 C4 112.30(9) . . ?
C11 C12 C4 103.95(9) . . ?
O4 C12 H5 111.1 . . ?
C11 C12 H5 111.1 . . ?
C4 C12 H5 111.1 . . ?
O5 C13 O4 118.08(10) . . ?
O5 C13 C6 126.37(11) . . ?
O4 C13 C6 115.53(9) . . ?
C2 C14 H9 109.5 . . ?
C2 C14 H11 109.5 . . ?
H9 C14 H11 109.5 . . ?
C2 C14 H10 109.5 . . ?
H9 C14 H10 109.5 . . ?
H11 C14 H10 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 O3 31.33(13) . . . . ?
C3 O1 C2 C14 147.72(11) . . . . ?
C3 O1 C2 C1 -87.01(13) . . . . ?
C11 O3 C2 O1 -34.57(13) . . . . ?
C11 O3 C2 C14 -150.48(11) . . . . ?
C11 O3 C2 C1 83.66(13) . . . . ?
C4 O2 C3 O1 95.01(11) . . . . ?
C4 O2 C3 C11 -19.07(12) . . . . ?
C2 O1 C3 O2 -132.25(10) . . . . ?
C2 O1 C3 C11 -16.14(13) . . . . ?
C3 O2 C4 C5 151.86(9) . . . . ?
C3 O2 C4 C12 30.61(12) . . . . ?
O2 C4 C5 C9 100.12(11) . . . . ?
C12 C4 C5 C9 -143.72(10) . . . . ?
O2 C4 C5 C6 -137.12(9) . . . . ?
C12 C4 C5 C6 -20.96(13) . . . . ?
C9 C5 C6 C13 -175.51(10) . . . . ?
C4 C5 C6 C13 59.15(12) . . . . ?
C9 C5 C6 C7 -50.38(12) . . . . ?
C4 C5 C6 C7 -175.72(9) . . . . ?
C13 C6 C7 C8 -172.91(10) . . . . ?
C5 C6 C7 C8 64.18(12) . . . . ?
C6 C7 C8 C10 -42.73(15) . . . . ?
C4 C5 C9 C10 141.47(13) . . . . ?
C6 C5 C9 C10 18.37(17) . . . . ?
C5 C9 C10 C8 1.3(2) . . . . ?
C7 C8 C10 C9 11.3(2) . . . . ?
C2 O3 C11 C12 135.43(9) . . . . ?
C2 O3 C11 C3 24.37(12) . . . . ?
O2 C3 C11 O3 113.83(10) . . . . ?
O1 C3 C11 O3 -5.07(12) . . . . ?
O2 C3 C11 C12 -0.28(13) . . . . ?
O1 C3 C11 C12 -119.18(10) . . . . ?
C13 O4 C12 C11 167.19(9) . . . . ?
C13 O4 C12 C4 53.83(13) . . . . ?
O3 C11 C12 O4 148.01(8) . . . . ?
C3 C11 C12 O4 -101.09(10) . . . . ?
O3 C11 C12 C4 -93.05(10) . . . . ?
C3 C11 C12 C4 17.84(12) . . . . ?
O2 C4 C12 O4 85.90(11) . . . . ?
C5 C4 C12 O4 -32.66(13) . . . . ?
O2 C4 C12 C11 -29.24(12) . . . . ?
C5 C4 C12 C11 -147.80(10) . . . . ?
C12 O4 C13 O5 167.93(10) . . . . ?
C12 O4 C13 C6 -13.67(13) . . . . ?
C7 C6 C13 O5 11.42(16) . . . . ?
C5 C6 C13 O5 135.14(12) . . . . ?
C7 C6 C13 O4 -166.83(10) . . . . ?
C5 C6 C13 O4 -43.11(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_tr1
_database_code_depnum_ccdc_archive 'CCDC 1032859'
_audit_update_record             
;
2014-11-05 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"(4aR,6aS,6bR,9aR,10aR,10bS)-4a,8,8-trimethyl-4,4a,6b,9a,10a,10b-hexahydro-3H-[1,3]dioxolo[4',5':4,5]furo[3,2-c] isochromen-5(6aH)-one"
_chemical_name_common            ?
_chemical_melting_point          331-333
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.0114(4)
_cell_length_b                   8.5390(5)
_cell_length_c                   23.6600(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1416.53(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5635
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         28.29
_reflns_number_total             3328
_reflns_number_gt                3113
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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)+(0.0447P)²+0.2035P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(8)
_refine_ls_number_reflns         3328
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_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 0.60733(13) 0.78625(11) 0.89141(5) 0.0290(2) Uani 1 1 d . . .
O2 O 0.24906(14) 0.51629(11) 0.84481(4) 0.0281(2) Uani 1 1 d . . .
O3 O 0.81901(15) 0.96355(14) 0.91106(6) 0.0469(3) Uani 1 1 d . . .
O4 O 0.28288(15) 0.88602(10) 0.82217(4) 0.0259(2) Uani 1 1 d . . .
O5 O 0.14398(14) 0.67618(11) 0.77515(5) 0.0305(2) Uani 1 1 d . . .
C1 C 0.5437(3) 1.0662(2) 1.01943(8) 0.0431(4) Uani 1 1 d . . .
H6 H 0.6556 0.9997 1.0214 0.052 Uiso 1 1 calc R . .
H1 H 0.5468 1.1370 1.0515 0.052 Uiso 1 1 calc R . .
C2 C 0.5477(2) 1.15994(18) 0.96495(7) 0.0314(3) Uani 1 1 d . . .
H5 H 0.6737 1.2049 0.9601 0.038 Uiso 1 1 calc R . .
H4 H 0.4572 1.2455 0.9678 0.038 Uiso 1 1 calc R . .
C3 C 0.49880(17) 1.06070(15) 0.91254(6) 0.0218(3) Uani 1 1 d . . .
C4 C 0.65216(18) 0.93473(16) 0.90621(6) 0.0251(3) Uani 1 1 d . . .
C5 C 0.41513(17) 0.72497(15) 0.89060(6) 0.0227(3) Uani 1 1 d . . .
H15 H 0.3882 0.6624 0.9244 0.027 Uiso 1 1 calc R . .
C6 C 0.39713(18) 0.62739(15) 0.83696(6) 0.0241(3) Uani 1 1 d . . .
H16 H 0.5179 0.5800 0.8250 0.029 Uiso 1 1 calc R . .
C7 C 0.13253(18) 0.51842(15) 0.79495(6) 0.0236(3) Uani 1 1 d . . .
C8 C 0.2104(2) 0.40798(18) 0.75042(7) 0.0342(3) Uani 1 1 d . . .
H3 H 0.3398 0.4359 0.7418 0.051 Uiso 1 1 calc R . .
H20 H 0.1343 0.4156 0.7168 0.051 Uiso 1 1 calc R . .
H2 H 0.2065 0.3025 0.7644 0.051 Uiso 1 1 calc R . .
C9 C 0.29639(17) 0.99268(15) 0.91887(6) 0.0223(3) Uani 1 1 d . . .
H9 H 0.2036 1.0734 0.9084 0.027 Uiso 1 1 calc R . .
C10 C 0.2557(2) 0.93988(18) 0.97857(7) 0.0329(3) Uani 1 1 d . . .
H8 H 0.1438 0.8842 0.9850 0.040 Uiso 1 1 calc R . .
C11 C 0.3678(3) 0.9673(2) 1.02237(7) 0.0423(4) Uani 1 1 d . . .
H7 H 0.3355 0.9226 1.0569 0.051 Uiso 1 1 calc R . .
C12 C 0.26536(18) 0.84989(14) 0.88155(6) 0.0206(3) Uani 1 1 d . . .
H11 H 0.1387 0.8059 0.8890 0.025 Uiso 1 1 calc R . .
C13 C 0.31585(19) 0.74379(15) 0.79346(6) 0.0239(3) Uani 1 1 d . . .
H10 H 0.4042 0.7586 0.7618 0.029 Uiso 1 1 calc R . .
C14 C 0.5139(3) 1.16718(17) 0.86021(7) 0.0346(4) Uani 1 1 d . . .
H12 H 0.4789 1.1090 0.8271 0.052 Uiso 1 1 calc R . .
H13 H 0.6427 1.2039 0.8564 0.052 Uiso 1 1 calc R . .
H14 H 0.4297 1.2550 0.8645 0.052 Uiso 1 1 calc R . .
C15 C -0.0703(2) 0.4851(2) 0.81137(7) 0.0379(4) Uani 1 1 d . . .
H17 H -0.1502 0.4907 0.7785 0.057 Uiso 1 1 calc R . .
H19 H -0.1119 0.5612 0.8386 0.057 Uiso 1 1 calc R . .
H18 H -0.0786 0.3822 0.8275 0.057 Uiso 1 1 calc R . .


_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 C4 1.3524(17) . ?
O1 C5 1.4458(15) . ?
O2 C6 1.4185(16) . ?
O2 C7 1.4352(16) . ?
O3 C4 1.2010(17) . ?
O4 C13 1.4105(15) . ?
O4 C12 1.4438(17) . ?
O5 C13 1.4048(16) . ?
O5 C7 1.4285(16) . ?
C1 C11 1.497(3) . ?
C1 C2 1.518(2) . ?
C1 H6 0.9700 . ?
C1 H1 0.9700 . ?
C2 C3 1.541(2) . ?
C2 H5 0.9700 . ?
C2 H4 0.9700 . ?
C3 C4 1.5283(18) . ?
C3 C14 1.540(2) . ?
C3 C9 1.5407(17) . ?
C5 C12 1.5120(17) . ?
C5 C6 1.5233(19) . ?
C5 H15 0.9800 . ?
C6 C13 1.5401(19) . ?
C6 H16 0.9800 . ?
C7 C15 1.5015(19) . ?
C7 C8 1.5157(19) . ?
C8 H3 0.9600 . ?
C8 H20 0.9600 . ?
C8 H2 0.9600 . ?
C9 C10 1.510(2) . ?
C9 C12 1.5210(17) . ?
C9 H9 0.9800 . ?
C10 C11 1.321(2) . ?
C10 H8 0.9300 . ?
C11 H7 0.9300 . ?
C12 H11 0.9800 . ?
C13 H10 0.9800 . ?
C14 H12 0.9600 . ?
C14 H13 0.9600 . ?
C14 H14 0.9600 . ?
C15 H17 0.9600 . ?
C15 H19 0.9600 . ?
C15 H18 0.9600 . ?

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
C4 O1 C5 124.01(10) . . ?
C6 O2 C7 107.49(10) . . ?
C13 O4 C12 107.37(9) . . ?
C13 O5 C7 109.55(10) . . ?
C11 C1 C2 110.63(14) . . ?
C11 C1 H6 109.5 . . ?
C2 C1 H6 109.5 . . ?
C11 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
H6 C1 H1 108.1 . . ?
C1 C2 C3 112.92(12) . . ?
C1 C2 H5 109.0 . . ?
C3 C2 H5 109.0 . . ?
C1 C2 H4 109.0 . . ?
C3 C2 H4 109.0 . . ?
H5 C2 H4 107.8 . . ?
C4 C3 C14 106.76(12) . . ?
C4 C3 C2 108.02(11) . . ?
C14 C3 C2 107.89(11) . . ?
C4 C3 C9 113.10(11) . . ?
C14 C3 C9 111.37(12) . . ?
C2 C3 C9 109.51(11) . . ?
O3 C4 O1 116.31(12) . . ?
O3 C4 C3 122.13(13) . . ?
O1 C4 C3 121.44(11) . . ?
O1 C5 C12 113.20(10) . . ?
O1 C5 C6 106.64(11) . . ?
C12 C5 C6 102.15(10) . . ?
O1 C5 H15 111.5 . . ?
C12 C5 H15 111.5 . . ?
C6 C5 H15 111.5 . . ?
O2 C6 C5 108.51(11) . . ?
O2 C6 C13 104.37(10) . . ?
C5 C6 C13 103.55(10) . . ?
O2 C6 H16 113.2 . . ?
C5 C6 H16 113.2 . . ?
C13 C6 H16 113.2 . . ?
O5 C7 O2 104.45(10) . . ?
O5 C7 C15 108.45(12) . . ?
O2 C7 C15 108.91(12) . . ?
O5 C7 C8 109.79(12) . . ?
O2 C7 C8 111.00(11) . . ?
C15 C7 C8 113.79(12) . . ?
C7 C8 H3 109.5 . . ?
C7 C8 H20 109.5 . . ?
H3 C8 H20 109.5 . . ?
C7 C8 H2 109.5 . . ?
H3 C8 H2 109.5 . . ?
H20 C8 H2 109.5 . . ?
C10 C9 C12 106.05(11) . . ?
C10 C9 C3 112.19(11) . . ?
C12 C9 C3 112.18(10) . . ?
C10 C9 H9 108.8 . . ?
C12 C9 H9 108.8 . . ?
C3 C9 H9 108.8 . . ?
C11 C10 C9 124.63(14) . . ?
C11 C10 H8 117.7 . . ?
C9 C10 H8 117.7 . . ?
C10 C11 C1 123.62(15) . . ?
C10 C11 H7 118.2 . . ?
C1 C11 H7 118.2 . . ?
O4 C12 C5 103.26(10) . . ?
O4 C12 C9 112.42(10) . . ?
C5 C12 C9 112.59(10) . . ?
O4 C12 H11 109.5 . . ?
C5 C12 H11 109.5 . . ?
C9 C12 H11 109.5 . . ?
O5 C13 O4 111.21(11) . . ?
O5 C13 C6 104.97(11) . . ?
O4 C13 C6 107.13(11) . . ?
O5 C13 H10 111.1 . . ?
O4 C13 H10 111.1 . . ?
C6 C13 H10 111.1 . . ?
C3 C14 H12 109.5 . . ?
C3 C14 H13 109.5 . . ?
H12 C14 H13 109.5 . . ?
C3 C14 H14 109.5 . . ?
H12 C14 H14 109.5 . . ?
H13 C14 H14 109.5 . . ?
C7 C15 H17 109.5 . . ?
C7 C15 H19 109.5 . . ?
H17 C15 H19 109.5 . . ?
C7 C15 H18 109.5 . . ?
H17 C15 H18 109.5 . . ?
H19 C15 H18 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 -46.5(2) . . . . ?
C1 C2 C3 C4 -63.14(16) . . . . ?
C1 C2 C3 C14 -178.20(14) . . . . ?
C1 C2 C3 C9 60.43(16) . . . . ?
C5 O1 C4 O3 171.82(14) . . . . ?
C5 O1 C4 C3 -12.0(2) . . . . ?
C14 C3 C4 O3 70.95(19) . . . . ?
C2 C3 C4 O3 -44.86(19) . . . . ?
C9 C3 C4 O3 -166.23(15) . . . . ?
C14 C3 C4 O1 -104.97(15) . . . . ?
C2 C3 C4 O1 139.22(14) . . . . ?
C9 C3 C4 O1 17.86(19) . . . . ?
C4 O1 C5 C12 26.18(18) . . . . ?
C4 O1 C5 C6 137.72(12) . . . . ?
C7 O2 C6 C5 134.12(11) . . . . ?
C7 O2 C6 C13 24.19(13) . . . . ?
O1 C5 C6 O2 156.24(10) . . . . ?
C12 C5 C6 O2 -84.75(12) . . . . ?
O1 C5 C6 C13 -93.27(12) . . . . ?
C12 C5 C6 C13 25.73(13) . . . . ?
C13 O5 C7 O2 25.99(14) . . . . ?
C13 O5 C7 C15 142.02(12) . . . . ?
C13 O5 C7 C8 -93.09(13) . . . . ?
C6 O2 C7 O5 -31.24(13) . . . . ?
C6 O2 C7 C15 -146.94(12) . . . . ?
C6 O2 C7 C8 87.02(13) . . . . ?
C4 C3 C9 C10 80.97(15) . . . . ?
C14 C3 C9 C10 -158.80(12) . . . . ?
C2 C3 C9 C10 -39.56(15) . . . . ?
C4 C3 C9 C12 -38.30(16) . . . . ?
C14 C3 C9 C12 81.94(14) . . . . ?
C2 C3 C9 C12 -158.82(11) . . . . ?
C12 C9 C10 C11 131.59(16) . . . . ?
C3 C9 C10 C11 8.8(2) . . . . ?
C9 C10 C11 C1 5.2(3) . . . . ?
C2 C1 C11 C10 13.8(3) . . . . ?
C13 O4 C12 C5 39.04(12) . . . . ?
C13 O4 C12 C9 160.64(10) . . . . ?
O1 C5 C12 O4 74.84(12) . . . . ?
C6 C5 C12 O4 -39.42(12) . . . . ?
O1 C5 C12 C9 -46.65(15) . . . . ?
C6 C5 C12 C9 -160.92(11) . . . . ?
C10 C9 C12 O4 174.87(11) . . . . ?
C3 C9 C12 O4 -62.33(14) . . . . ?
C10 C9 C12 C5 -69.01(13) . . . . ?
C3 C9 C12 C5 53.80(15) . . . . ?
C7 O5 C13 O4 -126.60(12) . . . . ?
C7 O5 C13 C6 -11.08(14) . . . . ?
C12 O4 C13 O5 92.03(13) . . . . ?
C12 O4 C13 C6 -22.16(13) . . . . ?
O2 C6 C13 O5 -8.11(13) . . . . ?
C5 C6 C13 O5 -121.62(11) . . . . ?
O2 C6 C13 O4 110.21(12) . . . . ?
C5 C6 C13 O4 -3.30(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_udct1m
_database_code_depnum_ccdc_archive 'CCDC 1053326'
_audit_update_record             
;
2015-03-11 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"(3S,3aS,6aR,8aR,8bR,11aR,12aR)-3,10,10-trimethyl-3a,4,5,6,8b,11a-hexahydro-3H indeno[4'',3a'':3',4']furo[2',3':4,5]furo[2,3-d][1,3]dioxol-7(8aH)-one"
_chemical_name_common            ?
_chemical_melting_point          395-397
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 O5'
_chemical_formula_weight         306.35

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

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

_cell_length_a                   8.3984(8)
_cell_length_b                   43.043(4)
_cell_length_c                   9.1804(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.838(2)
_cell_angle_gamma                90.00
_cell_volume                     3208.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6199
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      23.35

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18513
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         0.95
_diffrn_reflns_theta_max         27.00
_reflns_number_total             11334
_reflns_number_gt                8509
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_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 > 2sigma(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)+(0.0500P)²+0.4404P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(8)
_refine_ls_number_reflns         11334
_refine_ls_number_parameters     805
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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 0.1026(3) 0.95843(5) 0.6371(3) 0.0681(8) Uani 1 1 d . . .
O2 O 0.3558(3) 0.96641(5) 0.7885(3) 0.0560(6) Uani 1 1 d . . .
O3 O 0.1495(2) 0.90560(5) 0.6727(3) 0.0493(6) Uani 1 1 d . . .
O4 O 0.3639(3) 0.89208(5) 0.9723(3) 0.0547(6) Uani 1 1 d . . .
O5 O 0.2932(4) 0.84308(6) 0.9885(3) 0.0798(9) Uani 1 1 d . . .
O6 O 0.7195(3) 0.61376(6) 0.6419(3) 0.0627(7) Uani 1 1 d . . .
O7 O 0.8637(4) 0.61689(6) 0.8824(3) 0.0800(9) Uani 1 1 d . . .
O8 O 0.8178(3) 0.66984(5) 0.8752(2) 0.0521(6) Uani 1 1 d . . .
O9 O 0.5117(3) 0.68697(6) 0.6450(3) 0.0570(6) Uani 1 1 d . . .
O10 O 0.4725(3) 0.73469(6) 0.7161(3) 0.0735(8) Uani 1 1 d . . .
O11 O 0.9420(4) 0.87112(6) 0.3132(3) 0.0782(9) Uani 1 1 d . . .
O12 O 0.8228(4) 0.86336(6) 0.0691(3) 0.0789(9) Uani 1 1 d . . .
O13 O 0.8462(3) 0.91571(5) 0.0289(2) 0.0543(6) Uani 1 1 d . . .
O14 O 1.1292(3) 0.94331(6) 0.2513(3) 0.0591(7) Uani 1 1 d . . .
O15 O 1.1593(3) 0.98724(7) 0.1356(3) 0.0740(8) Uani 1 1 d . . .
O16 O 0.2510(3) 0.72008(5) 0.0775(3) 0.0623(7) Uani 1 1 d . . .
O17 O 0.5205(3) 0.72356(6) 0.1880(4) 0.0755(8) Uani 1 1 d . . .
O18 O 0.5230(3) 0.67002(5) 0.1908(3) 0.0620(7) Uani 1 1 d . . .
O19 O 0.2861(3) 0.64487(5) -0.0847(3) 0.0518(6) Uani 1 1 d . . .
O20 O 0.3862(3) 0.59763(6) -0.0972(3) 0.0669(7) Uani 1 1 d . . .
C56 C 0.2589(4) 0.66607(7) 0.0289(4) 0.0462(8) Uani 1 1 d . . .
H56 H 0.1426 0.6670 0.0298 0.055 Uiso 1 1 calc R . .
C52 C 0.3253(4) 0.69728(8) 0.0046(4) 0.0518(8) Uani 1 1 d . . .
H52 H 0.3164 0.7019 -0.1017 0.062 Uiso 1 1 calc R . .
C54 C 0.5028(4) 0.69683(7) 0.1017(4) 0.0529(9) Uani 1 1 d . . .
H54 H 0.5803 0.6969 0.0380 0.063 Uiso 1 1 calc R . .
C57 C 0.3587(4) 0.61858(8) -0.0202(4) 0.0473(8) Uani 1 1 d . . .
C55 C 0.3684(4) 0.65444(7) 0.1795(4) 0.0430(8) Uani 1 1 d . . .
C62 C 0.2746(4) 0.59717(7) 0.2047(4) 0.0486(8) Uani 1 1 d . . .
H62 H 0.2284 0.5826 0.1228 0.058 Uiso 1 1 calc R . .
C63 C 0.1308(4) 0.61374(9) 0.2464(4) 0.0582(10) Uani 1 1 d . . .
H63 H 0.0581 0.6216 0.1526 0.070 Uiso 1 1 calc R . .
C65 C 0.3025(5) 0.65981(8) 0.3125(4) 0.0542(9) Uani 1 1 d . . .
H65 H 0.3398 0.6767 0.3751 0.065 Uiso 1 1 calc R . .
C58 C 0.3935(4) 0.61978(7) 0.1492(4) 0.0437(8) Uani 1 1 d . . .
C64 C 0.1918(5) 0.64092(9) 0.3433(4) 0.0604(10) Uani 1 1 d . . .
H64 H 0.1514 0.6448 0.4269 0.073 Uiso 1 1 calc R . .
C59 C 0.5694(4) 0.60775(8) 0.2264(4) 0.0546(9) Uani 1 1 d . . .
H59A H 0.6363 0.6068 0.1546 0.065 Uiso 1 1 calc R . .
H59B H 0.6230 0.6213 0.3088 0.065 Uiso 1 1 calc R . .
C61 C 0.3879(5) 0.57891(8) 0.3329(5) 0.0626(10) Uani 1 1 d . . .
H61A H 0.4067 0.5902 0.4273 0.075 Uiso 1 1 calc R . .
H61B H 0.3414 0.5587 0.3448 0.075 Uiso 1 1 calc R . .
C53 C 0.3747(5) 0.74161(8) 0.1479(5) 0.0594(10) Uani 1 1 d . . .
C60 C 0.5451(5) 0.57558(9) 0.2845(5) 0.0646(10) Uani 1 1 d . . .
H60A H 0.5339 0.5601 0.2057 0.077 Uiso 1 1 calc R . .
H60B H 0.6362 0.5699 0.3688 0.077 Uiso 1 1 calc R . .
C67 C 0.3355(7) 0.75388(11) 0.2875(6) 0.0968(15) Uani 1 1 d . . .
H67A H 0.3412 0.7373 0.3584 0.145 Uiso 1 1 calc R . .
H67B H 0.2266 0.7626 0.2620 0.145 Uiso 1 1 calc R . .
H67C H 0.4137 0.7697 0.3315 0.145 Uiso 1 1 calc R . .
C68 C 0.0291(6) 0.59103(12) 0.3153(6) 0.0924(15) Uani 1 1 d . . .
H68A H -0.0615 0.6019 0.3379 0.139 Uiso 1 1 calc R . .
H68B H 0.0975 0.5823 0.4062 0.139 Uiso 1 1 calc R . .
H68C H -0.0124 0.5747 0.2447 0.139 Uiso 1 1 calc R . .
C66 C 0.3937(6) 0.76693(9) 0.0412(6) 0.0880(14) Uani 1 1 d . . .
H66A H 0.2956 0.7794 0.0163 0.132 Uiso 1 1 calc R . .
H66B H 0.4113 0.7579 -0.0489 0.132 Uiso 1 1 calc R . .
H66C H 0.4862 0.7797 0.0881 0.132 Uiso 1 1 calc R . .
C39 C 0.9991(4) 0.92396(8) 0.2767(4) 0.0504(9) Uani 1 1 d . . .
H39 H 0.9874 0.9260 0.3798 0.060 Uiso 1 1 calc R . .
C11 C 0.5029(4) 0.84733(7) 0.7378(4) 0.0420(7) Uani 1 1 d . . .
H11 H 0.5525 0.8366 0.8328 0.050 Uiso 1 1 calc R . .
C6 C 0.3344(4) 0.86236(7) 0.7516(4) 0.0414(7) Uani 1 1 d . . .
C8 C 0.4020(4) 0.90504(7) 0.5862(4) 0.0427(8) Uani 1 1 d . . .
H8 H 0.3504 0.9184 0.5089 0.051 Uiso 1 1 calc R . .
C10 C 0.6289(4) 0.87136(8) 0.7109(4) 0.0452(8) Uani 1 1 d . . .
H10 H 0.6642 0.8837 0.8033 0.054 Uiso 1 1 calc R . .
C4 C 0.3926(4) 0.91343(8) 0.8594(4) 0.0434(8) Uani 1 1 d . . .
H4 H 0.5096 0.9185 0.8749 0.052 Uiso 1 1 calc R . .
C40 C 1.0688(4) 0.96862(8) 0.1647(4) 0.0498(9) Uani 1 1 d . . .
C5 C 0.3265(4) 0.86341(8) 0.9129(4) 0.0495(9) Uani 1 1 d . . .
C41 C 0.8824(4) 0.96810(8) 0.1217(4) 0.0475(8) Uani 1 1 d . . .
C3 C 0.2879(4) 0.94199(8) 0.8553(4) 0.0484(8) Uani 1 1 d . . .
H3 H 0.2717 0.9475 0.9541 0.058 Uiso 1 1 calc R . .
C7 C 0.3208(3) 0.89710(7) 0.7085(4) 0.0379(7) Uani 1 1 d . . .
C38 C 0.8436(4) 0.93466(7) 0.1592(4) 0.0448(8) Uani 1 1 d . . .
C9 C 0.5456(4) 0.89312(8) 0.5881(4) 0.0493(8) Uani 1 1 d . . .
H9 H 0.5964 0.8982 0.5124 0.059 Uiso 1 1 calc R . .
C48 C 0.6862(4) 0.93157(9) 0.2057(4) 0.0551(9) Uani 1 1 d . . .
H48 H 0.6177 0.9146 0.1740 0.066 Uiso 1 1 calc R . .
C14 C 0.2003(4) 0.84128(8) 0.6538(4) 0.0548(9) Uani 1 1 d . . .
H14A H 0.1144 0.8371 0.7045 0.066 Uiso 1 1 calc R . .
H14B H 0.1511 0.8511 0.5576 0.066 Uiso 1 1 calc R . .
C35 C 1.0262(5) 0.89090(8) 0.2374(4) 0.0618(11) Uani 1 1 d . . .
H35 H 1.1431 0.8856 0.2551 0.074 Uiso 1 1 calc R . .
C2 C 0.1276(4) 0.93404(7) 0.7396(4) 0.0474(8) Uani 1 1 d . . .
H2 H 0.0364 0.9327 0.7878 0.057 Uiso 1 1 calc R . .
C47 C 0.6454(5) 0.95283(11) 0.2908(5) 0.0673(11) Uani 1 1 d . . .
H47 H 0.5471 0.9509 0.3189 0.081 Uiso 1 1 calc R . .
C17 C 0.7829(4) 0.85599(10) 0.6843(5) 0.0660(11) Uani 1 1 d . . .
H17A H 0.8603 0.8717 0.6738 0.099 Uiso 1 1 calc R . .
H17B H 0.7533 0.8437 0.5939 0.099 Uiso 1 1 calc R . .
H17C H 0.8320 0.8429 0.7683 0.099 Uiso 1 1 calc R . .
C12 C 0.4510(4) 0.82276(8) 0.6158(5) 0.0590(10) Uani 1 1 d . . .
H12A H 0.4413 0.8316 0.5168 0.071 Uiso 1 1 calc R . .
H12B H 0.5299 0.8059 0.6315 0.071 Uiso 1 1 calc R . .
C13 C 0.2866(4) 0.81161(9) 0.6314(5) 0.0631(10) Uani 1 1 d . . .
H13A H 0.2992 0.7979 0.7174 0.076 Uiso 1 1 calc R . .
H13B H 0.2267 0.8008 0.5413 0.076 Uiso 1 1 calc R . .
C45 C 0.8141(5) 0.99335(8) 0.2123(5) 0.0600(10) Uani 1 1 d . . .
H45 H 0.9047 1.0077 0.2548 0.072 Uiso 1 1 calc R . .
C15 C 0.1563(6) 1.00777(9) 0.7660(6) 0.0758(12) Uani 1 1 d . . .
H15A H 0.2379 1.0238 0.7956 0.114 Uiso 1 1 calc R . .
H15B H 0.1286 0.9996 0.8536 0.114 Uiso 1 1 calc R . .
H15C H 0.0595 1.0163 0.6985 0.114 Uiso 1 1 calc R . .
C36 C 0.8635(6) 0.84788(9) 0.2096(4) 0.0768(13) Uani 1 1 d . . .
C37 C 0.9310(5) 0.88786(8) 0.0712(4) 0.0574(10) Uani 1 1 d . . .
H37 H 1.0057 0.8834 0.0075 0.069 Uiso 1 1 calc R . .
C1 C 0.2241(4) 0.98194(7) 0.6872(4) 0.0536(9) Uani 1 1 d . . .
C46 C 0.7541(5) 0.98024(10) 0.3438(5) 0.0686(11) Uani 1 1 d . . .
H46 H 0.8511 0.9728 0.4195 0.082 Uiso 1 1 calc R . .
C16 C 0.2818(6) 0.99403(10) 0.5558(5) 0.0793(12) Uani 1 1 d . . .
H16A H 0.3161 0.9770 0.5038 0.119 Uiso 1 1 calc R . .
H16B H 0.3727 1.0079 0.5915 0.119 Uiso 1 1 calc R . .
H16C H 0.1932 1.0049 0.4881 0.119 Uiso 1 1 calc R . .
C51 C 0.6713(7) 1.00522(13) 0.4196(7) 0.116(2) Uani 1 1 d . . .
H51A H 0.6425 0.9964 0.5055 0.173 Uiso 1 1 calc R . .
H51B H 0.5735 1.0126 0.3491 0.173 Uiso 1 1 calc R . .
H51C H 0.7461 1.0222 0.4514 0.173 Uiso 1 1 calc R . .
C50 C 0.9822(8) 0.82131(10) 0.2072(6) 0.118(2) Uani 1 1 d . . .
H50A H 1.0773 0.8291 0.1793 0.177 Uiso 1 1 calc R . .
H50B H 0.9286 0.8060 0.1352 0.177 Uiso 1 1 calc R . .
H50C H 1.0155 0.8120 0.3054 0.177 Uiso 1 1 calc R . .
C49 C 0.7084(8) 0.83820(12) 0.2469(6) 0.1116(19) Uani 1 1 d . . .
H49A H 0.6485 0.8243 0.1707 0.167 Uiso 1 1 calc R . .
H49B H 0.6422 0.8562 0.2511 0.167 Uiso 1 1 calc R . .
H49C H 0.7343 0.8279 0.3428 0.167 Uiso 1 1 calc R . .
C21 C 0.8026(4) 0.68295(7) 0.7270(3) 0.0428(8) Uani 1 1 d . . .
C22 C 0.6473(4) 0.66728(8) 0.6311(4) 0.0466(8) Uani 1 1 d . . .
H22 H 0.6512 0.6648 0.5260 0.056 Uiso 1 1 calc R . .
C24 C 0.7518(4) 0.71725(8) 0.7313(4) 0.0475(8) Uani 1 1 d . . .
C18 C 0.6360(4) 0.63645(8) 0.7055(4) 0.0528(9) Uani 1 1 d . . .
H18 H 0.5226 0.6305 0.7027 0.063 Uiso 1 1 calc R . .
C28 C 0.7997(4) 0.73761(9) 0.6068(5) 0.0599(10) Uani 1 1 d . . .
H28 H 0.7019 0.7495 0.5554 0.072 Uiso 1 1 calc R . .
C30 C 0.9790(4) 0.69551(9) 0.5633(4) 0.0593(10) Uani 1 1 d . . .
H30 H 1.0749 0.6929 0.5317 0.071 Uiso 1 1 calc R . .
C20 C 0.7449(5) 0.64043(9) 0.8661(4) 0.0555(9) Uani 1 1 d . . .
H20 H 0.6804 0.6382 0.9406 0.067 Uiso 1 1 calc R . .
C23 C 0.5676(4) 0.71516(8) 0.6999(4) 0.0504(9) Uani 1 1 d . . .
C25 C 0.8306(5) 0.73406(9) 0.8824(5) 0.0697(11) Uani 1 1 d . . .
H25A H 0.7535 0.7351 0.9450 0.084 Uiso 1 1 calc R . .
H25B H 0.9290 0.7233 0.9374 0.084 Uiso 1 1 calc R . .
C31 C 0.9549(4) 0.67835(8) 0.6736(4) 0.0476(8) Uani 1 1 d . . .
H31 H 1.0319 0.6634 0.7184 0.057 Uiso 1 1 calc R . .
C29 C 0.8553(5) 0.71908(9) 0.4877(4) 0.0618(10) Uani 1 1 d . . .
H29 H 0.7591 0.7078 0.4285 0.074 Uiso 1 1 calc R . .
C19 C 0.8182(5) 0.59578(8) 0.7615(4) 0.0603(10) Uani 1 1 d . . .
C32 C 0.9691(5) 0.58565(10) 0.7156(6) 0.0857(14) Uani 1 1 d . . .
H32A H 1.0375 0.5734 0.7946 0.129 Uiso 1 1 calc R . .
H32B H 1.0291 0.6036 0.6976 0.129 Uiso 1 1 calc R . .
H32C H 0.9372 0.5735 0.6252 0.129 Uiso 1 1 calc R . .
C34 C 0.9177(7) 0.74004(12) 0.3776(6) 0.0956(15) Uani 1 1 d . . .
H34A H 0.9348 0.7277 0.2958 0.143 Uiso 1 1 calc R . .
H34B H 1.0196 0.7496 0.4297 0.143 Uiso 1 1 calc R . .
H34C H 0.8374 0.7558 0.3388 0.143 Uiso 1 1 calc R . .
C33 C 0.7219(7) 0.56838(10) 0.7978(7) 0.0941(16) Uani 1 1 d . . .
H33A H 0.6232 0.5757 0.8209 0.141 Uiso 1 1 calc R . .
H33B H 0.7880 0.5574 0.8830 0.141 Uiso 1 1 calc R . .
H33C H 0.6935 0.5547 0.7125 0.141 Uiso 1 1 calc R . .
C27 C 0.9268(6) 0.76069(9) 0.6961(6) 0.0832(14) Uani 1 1 d . . .
H27A H 1.0367 0.7519 0.7190 0.100 Uiso 1 1 calc R . .
H27B H 0.9259 0.7798 0.6400 0.100 Uiso 1 1 calc R . .
C26 C 0.8728(6) 0.76650(10) 0.8385(6) 0.0872(15) Uani 1 1 d . . .
H26A H 0.7775 0.7801 0.8197 0.105 Uiso 1 1 calc R . .
H26B H 0.9610 0.7756 0.9163 0.105 Uiso 1 1 calc R . .
C42 C 0.8102(5) 0.97689(8) -0.0455(4) 0.0593(10) Uani 1 1 d . . .
H42A H 0.8932 0.9749 -0.1014 0.071 Uiso 1 1 calc R . .
H42B H 0.7179 0.9636 -0.0912 0.071 Uiso 1 1 calc R . .
C43 C 0.7547(6) 1.01032(10) -0.0448(6) 0.0846(14) Uani 1 1 d . . .
H43A H 0.8463 1.0246 -0.0349 0.102 Uiso 1 1 calc R . .
H43B H 0.6702 1.0153 -0.1356 0.102 Uiso 1 1 calc R . .
C44 C 0.6874(6) 1.01120(10) 0.0927(6) 0.0866(15) Uani 1 1 d . . .
H44A H 0.5803 1.0012 0.0725 0.104 Uiso 1 1 calc R . .
H44B H 0.6771 1.0324 0.1246 0.104 Uiso 1 1 calc R . .


_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 C2 1.389(4) . ?
O1 C1 1.427(4) . ?
O2 C3 1.409(4) . ?
O2 C1 1.417(4) . ?
O3 C2 1.403(4) . ?
O3 C7 1.439(3) . ?
O4 C5 1.353(4) . ?
O4 C4 1.451(4) . ?
O5 C5 1.194(4) . ?
O6 C18 1.413(4) . ?
O6 C19 1.423(4) . ?
O7 C20 1.403(5) . ?
O7 C19 1.410(5) . ?
O8 C20 1.400(4) . ?
O8 C21 1.448(4) . ?
O9 C23 1.351(4) . ?
O9 C22 1.452(4) . ?
O10 C23 1.195(4) . ?
O11 C35 1.400(5) . ?
O11 C36 1.420(5) . ?
O12 C37 1.389(5) . ?
O12 C36 1.413(5) . ?
O13 C37 1.398(4) . ?
O13 C38 1.453(4) . ?
O14 C40 1.367(4) . ?
O14 C39 1.440(4) . ?
O15 C40 1.181(4) . ?
O16 C53 1.419(4) . ?
O16 C52 1.419(4) . ?
O17 C54 1.383(4) . ?
O17 C53 1.417(4) . ?
O18 C54 1.400(4) . ?
O18 C55 1.441(4) . ?
O19 C57 1.348(4) . ?
O19 C56 1.448(4) . ?
O20 C57 1.204(4) . ?
C56 C52 1.493(5) . ?
C56 C55 1.535(5) . ?
C56 H56 0.9800 . ?
C52 C54 1.528(5) . ?
C52 H52 0.9800 . ?
C54 H54 0.9800 . ?
C57 C58 1.508(5) . ?
C55 C65 1.482(5) . ?
C55 C58 1.542(4) . ?
C62 C61 1.528(5) . ?
C62 C63 1.533(5) . ?
C62 C58 1.571(5) . ?
C62 H62 0.9800 . ?
C63 C64 1.479(5) . ?
C63 C68 1.537(5) . ?
C63 H63 0.9800 . ?
C65 C64 1.319(5) . ?
C65 H65 0.9300 . ?
C58 C59 1.554(4) . ?
C64 H64 0.9300 . ?
C59 C60 1.516(5) . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?
C61 C60 1.504(5) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C53 C67 1.498(6) . ?
C53 C66 1.501(6) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C67 H67A 0.9600 . ?
C67 H67B 0.9600 . ?
C67 H67C 0.9600 . ?
C68 H68A 0.9600 . ?
C68 H68B 0.9600 . ?
C68 H68C 0.9600 . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
C39 C35 1.500(5) . ?
C39 C38 1.536(5) . ?
C39 H39 0.9800 . ?
C11 C12 1.521(5) . ?
C11 C10 1.544(5) . ?
C11 C6 1.590(4) . ?
C11 H11 0.9800 . ?
C6 C5 1.500(5) . ?
C6 C14 1.543(5) . ?
C6 C7 1.543(4) . ?
C8 C9 1.307(5) . ?
C8 C7 1.495(5) . ?
C8 H8 0.9300 . ?
C10 C9 1.494(5) . ?
C10 C17 1.527(5) . ?
C10 H10 0.9800 . ?
C4 C3 1.506(5) . ?
C4 C7 1.533(4) . ?
C4 H4 0.9800 . ?
C40 C41 1.514(5) . ?
C41 C38 1.534(5) . ?
C41 C42 1.546(5) . ?
C41 C45 1.564(5) . ?
C3 C2 1.525(5) . ?
C3 H3 0.9800 . ?
C38 C48 1.495(5) . ?
C9 H9 0.9300 . ?
C48 C47 1.304(5) . ?
C48 H48 0.9300 . ?
C14 C13 1.508(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C35 C37 1.536(5) . ?
C35 H35 0.9800 . ?
C2 H2 0.9800 . ?
C47 C46 1.495(6) . ?
C47 H47 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C12 C13 1.502(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C45 C44 1.526(6) . ?
C45 C46 1.531(6) . ?
C45 H45 0.9800 . ?
C15 C1 1.514(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C36 C49 1.489(7) . ?
C36 C50 1.521(7) . ?
C37 H37 0.9800 . ?
C1 C16 1.504(6) . ?
C46 C51 1.540(6) . ?
C46 H46 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C21 C31 1.495(5) . ?
C21 C22 1.531(4) . ?
C21 C24 1.540(4) . ?
C22 C18 1.506(5) . ?
C22 H22 0.9800 . ?
C24 C23 1.502(5) . ?
C24 C25 1.554(5) . ?
C24 C28 1.572(5) . ?
C18 C20 1.533(5) . ?
C18 H18 0.9800 . ?
C28 C29 1.520(5) . ?
C28 C27 1.533(6) . ?
C28 H28 0.9800 . ?
C30 C31 1.310(5) . ?
C30 C29 1.490(5) . ?
C30 H30 0.9300 . ?
C20 H20 0.9800 . ?
C25 C26 1.520(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C31 H31 0.9300 . ?
C29 C34 1.543(6) . ?
C29 H29 0.9800 . ?
C19 C32 1.499(6) . ?
C19 C33 1.515(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C27 C26 1.510(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C42 C43 1.513(5) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.510(7) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?

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
C2 O1 C1 110.2(3) . . ?
C3 O2 C1 107.6(3) . . ?
C2 O3 C7 110.9(2) . . ?
C5 O4 C4 110.7(3) . . ?
C18 O6 C19 108.1(3) . . ?
C20 O7 C19 109.8(3) . . ?
C20 O8 C21 111.4(2) . . ?
C23 O9 C22 110.6(3) . . ?
C35 O11 C36 107.6(3) . . ?
C37 O12 C36 109.9(3) . . ?
C37 O13 C38 111.5(2) . . ?
C40 O14 C39 111.8(3) . . ?
C53 O16 C52 107.9(3) . . ?
C54 O17 C53 110.4(3) . . ?
C54 O18 C55 111.7(2) . . ?
C57 O19 C56 110.4(2) . . ?
O19 C56 C52 109.0(3) . . ?
O19 C56 C55 106.0(2) . . ?
C52 C56 C55 105.5(3) . . ?
O19 C56 H56 112.0 . . ?
C52 C56 H56 112.0 . . ?
C55 C56 H56 112.0 . . ?
O16 C52 C56 109.0(3) . . ?
O16 C52 C54 102.4(3) . . ?
C56 C52 C54 104.3(3) . . ?
O16 C52 H52 113.4 . . ?
C56 C52 H52 113.4 . . ?
C54 C52 H52 113.4 . . ?
O17 C54 O18 111.8(3) . . ?
O17 C54 C52 105.6(3) . . ?
O18 C54 C52 107.8(3) . . ?
O17 C54 H54 110.5 . . ?
O18 C54 H54 110.5 . . ?
C52 C54 H54 110.5 . . ?
O20 C57 O19 120.2(3) . . ?
O20 C57 C58 128.0(3) . . ?
O19 C57 C58 111.8(3) . . ?
O18 C55 C65 112.8(3) . . ?
O18 C55 C56 103.5(3) . . ?
C65 C55 C56 115.3(3) . . ?
O18 C55 C58 107.5(2) . . ?
C65 C55 C58 113.4(3) . . ?
C56 C55 C58 103.3(3) . . ?
C61 C62 C63 115.0(3) . . ?
C61 C62 C58 104.2(3) . . ?
C63 C62 C58 113.6(3) . . ?
C61 C62 H62 107.9 . . ?
C63 C62 H62 107.9 . . ?
C58 C62 H62 107.9 . . ?
C64 C63 C62 110.2(3) . . ?
C64 C63 C68 113.5(4) . . ?
C62 C63 C68 111.3(3) . . ?
C64 C63 H63 107.2 . . ?
C62 C63 H63 107.2 . . ?
C68 C63 H63 107.2 . . ?
C64 C65 C55 120.8(3) . . ?
C64 C65 H65 119.6 . . ?
C55 C65 H65 119.6 . . ?
C57 C58 C55 102.7(3) . . ?
C57 C58 C59 111.7(3) . . ?
C55 C58 C59 113.5(3) . . ?
C57 C58 C62 110.0(3) . . ?
C55 C58 C62 114.4(3) . . ?
C59 C58 C62 104.7(3) . . ?
C65 C64 C63 120.9(3) . . ?
C65 C64 H64 119.6 . . ?
C63 C64 H64 119.6 . . ?
C60 C59 C58 105.5(3) . . ?
C60 C59 H59A 110.6 . . ?
C58 C59 H59A 110.6 . . ?
C60 C59 H59B 110.6 . . ?
C58 C59 H59B 110.6 . . ?
H59A C59 H59B 108.8 . . ?
C60 C61 C62 104.0(3) . . ?
C60 C61 H61A 110.9 . . ?
C62 C61 H61A 110.9 . . ?
C60 C61 H61B 110.9 . . ?
C62 C61 H61B 110.9 . . ?
H61A C61 H61B 109.0 . . ?
O17 C53 O16 104.1(3) . . ?
O17 C53 C67 109.6(4) . . ?
O16 C53 C67 109.0(3) . . ?
O17 C53 C66 109.8(3) . . ?
O16 C53 C66 111.4(3) . . ?
C67 C53 C66 112.7(3) . . ?
C61 C60 C59 102.9(3) . . ?
C61 C60 H60A 111.2 . . ?
C59 C60 H60A 111.2 . . ?
C61 C60 H60B 111.2 . . ?
C59 C60 H60B 111.2 . . ?
H60A C60 H60B 109.1 . . ?
C53 C67 H67A 109.5 . . ?
C53 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C53 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C63 C68 H68A 109.5 . . ?
C63 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C63 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C53 C66 H66A 109.5 . . ?
C53 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C53 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
O14 C39 C35 110.0(3) . . ?
O14 C39 C38 104.9(3) . . ?
C35 C39 C38 105.7(3) . . ?
O14 C39 H39 112.0 . . ?
C35 C39 H39 112.0 . . ?
C38 C39 H39 112.0 . . ?
C12 C11 C10 115.3(3) . . ?
C12 C11 C6 104.4(3) . . ?
C10 C11 C6 113.6(3) . . ?
C12 C11 H11 107.7 . . ?
C10 C11 H11 107.7 . . ?
C6 C11 H11 107.7 . . ?
C5 C6 C14 112.5(3) . . ?
C5 C6 C7 101.8(3) . . ?
C14 C6 C7 115.2(3) . . ?
C5 C6 C11 110.9(3) . . ?
C14 C6 C11 104.3(3) . . ?
C7 C6 C11 112.5(2) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C9 C10 C17 113.8(3) . . ?
C9 C10 C11 109.4(3) . . ?
C17 C10 C11 112.3(3) . . ?
C9 C10 H10 107.0 . . ?
C17 C10 H10 107.0 . . ?
C11 C10 H10 107.0 . . ?
O4 C4 C3 109.4(3) . . ?
O4 C4 C7 104.8(2) . . ?
C3 C4 C7 105.0(3) . . ?
O4 C4 H4 112.3 . . ?
C3 C4 H4 112.3 . . ?
C7 C4 H4 112.3 . . ?
O15 C40 O14 120.5(3) . . ?
O15 C40 C41 129.3(4) . . ?
O14 C40 C41 110.1(3) . . ?
O5 C5 O4 119.9(3) . . ?
O5 C5 C6 128.9(3) . . ?
O4 C5 C6 111.2(3) . . ?
C40 C41 C38 102.7(3) . . ?
C40 C41 C42 111.8(3) . . ?
C38 C41 C42 113.6(3) . . ?
C40 C41 C45 110.3(3) . . ?
C38 C41 C45 113.9(3) . . ?
C42 C41 C45 104.7(3) . . ?
O2 C3 C4 108.7(3) . . ?
O2 C3 C2 104.3(3) . . ?
C4 C3 C2 103.9(3) . . ?
O2 C3 H3 113.0 . . ?
C4 C3 H3 113.0 . . ?
C2 C3 H3 113.0 . . ?
O3 C7 C8 113.1(3) . . ?
O3 C7 C4 103.2(2) . . ?
C8 C7 C4 115.1(2) . . ?
O3 C7 C6 108.0(2) . . ?
C8 C7 C6 113.3(3) . . ?
C4 C7 C6 103.1(2) . . ?
O13 C38 C48 112.7(3) . . ?
O13 C38 C41 107.0(3) . . ?
C48 C38 C41 113.7(3) . . ?
O13 C38 C39 102.7(3) . . ?
C48 C38 C39 115.3(3) . . ?
C41 C38 C39 104.3(3) . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C47 C48 C38 119.7(3) . . ?
C47 C48 H48 120.1 . . ?
C38 C48 H48 120.1 . . ?
C13 C14 C6 105.8(3) . . ?
C13 C14 H14A 110.6 . . ?
C6 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C6 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
O11 C35 C39 109.3(3) . . ?
O11 C35 C37 103.9(3) . . ?
C39 C35 C37 104.3(3) . . ?
O11 C35 H35 112.9 . . ?
C39 C35 H35 112.9 . . ?
C37 C35 H35 112.9 . . ?
O1 C2 O3 112.1(3) . . ?
O1 C2 C3 104.8(3) . . ?
O3 C2 C3 108.0(2) . . ?
O1 C2 H2 110.6 . . ?
O3 C2 H2 110.6 . . ?
C3 C2 H2 110.6 . . ?
C48 C47 C46 121.1(4) . . ?
C48 C47 H47 119.5 . . ?
C46 C47 H47 119.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C12 C11 104.4(3) . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C12 C13 C14 103.2(3) . . ?
C12 C13 H13A 111.1 . . ?
C14 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
C14 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
C44 C45 C46 116.3(4) . . ?
C44 C45 C41 104.5(3) . . ?
C46 C45 C41 113.7(3) . . ?
C44 C45 H45 107.3 . . ?
C46 C45 H45 107.3 . . ?
C41 C45 H45 107.3 . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O12 C36 O11 104.0(3) . . ?
O12 C36 C49 108.7(4) . . ?
O11 C36 C49 109.1(4) . . ?
O12 C36 C50 110.3(4) . . ?
O11 C36 C50 110.2(4) . . ?
C49 C36 C50 114.1(4) . . ?
O12 C37 O13 111.2(3) . . ?
O12 C37 C35 104.5(3) . . ?
O13 C37 C35 107.6(3) . . ?
O12 C37 H37 111.1 . . ?
O13 C37 H37 111.1 . . ?
C35 C37 H37 111.1 . . ?
O2 C1 O1 104.5(2) . . ?
O2 C1 C16 109.4(3) . . ?
O1 C1 C16 109.7(3) . . ?
O2 C1 C15 111.0(3) . . ?
O1 C1 C15 110.5(3) . . ?
C16 C1 C15 111.5(3) . . ?
C47 C46 C45 109.3(3) . . ?
C47 C46 C51 112.9(4) . . ?
C45 C46 C51 112.1(4) . . ?
C47 C46 H46 107.4 . . ?
C45 C46 H46 107.4 . . ?
C51 C46 H46 107.4 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C46 C51 H51A 109.5 . . ?
C46 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C46 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C36 C50 H50A 109.5 . . ?
C36 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C36 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C36 C49 H49A 109.5 . . ?
C36 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C36 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
O8 C21 C31 112.3(3) . . ?
O8 C21 C22 103.0(2) . . ?
C31 C21 C22 115.3(3) . . ?
O8 C21 C24 107.9(3) . . ?
C31 C21 C24 113.7(3) . . ?
C22 C21 C24 103.7(3) . . ?
O9 C22 C18 109.5(3) . . ?
O9 C22 C21 105.3(3) . . ?
C18 C22 C21 105.7(3) . . ?
O9 C22 H22 112.0 . . ?
C18 C22 H22 112.0 . . ?
C21 C22 H22 112.0 . . ?
C23 C24 C21 102.5(3) . . ?
C23 C24 C25 112.4(3) . . ?
C21 C24 C25 114.3(3) . . ?
C23 C24 C28 109.7(3) . . ?
C21 C24 C28 113.0(3) . . ?
C25 C24 C28 105.1(3) . . ?
O6 C18 C22 109.0(3) . . ?
O6 C18 C20 103.8(3) . . ?
C22 C18 C20 104.3(3) . . ?
O6 C18 H18 113.0 . . ?
C22 C18 H18 113.0 . . ?
C20 C18 H18 113.0 . . ?
C29 C28 C27 115.1(3) . . ?
C29 C28 C24 114.4(3) . . ?
C27 C28 C24 104.2(3) . . ?
C29 C28 H28 107.6 . . ?
C27 C28 H28 107.6 . . ?
C24 C28 H28 107.6 . . ?
C31 C30 C29 121.1(3) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
O8 C20 O7 111.0(3) . . ?
O8 C20 C18 107.6(3) . . ?
O7 C20 C18 104.8(3) . . ?
O8 C20 H20 111.1 . . ?
O7 C20 H20 111.1 . . ?
C18 C20 H20 111.1 . . ?
O10 C23 O9 119.9(3) . . ?
O10 C23 C24 128.5(3) . . ?
O9 C23 C24 111.6(3) . . ?
C26 C25 C24 105.4(4) . . ?
C26 C25 H25A 110.7 . . ?
C24 C25 H25A 110.7 . . ?
C26 C25 H25B 110.7 . . ?
C24 C25 H25B 110.7 . . ?
H25A C25 H25B 108.8 . . ?
C30 C31 C21 119.6(3) . . ?
C30 C31 H31 120.2 . . ?
C21 C31 H31 120.2 . . ?
C30 C29 C28 109.2(3) . . ?
C30 C29 C34 113.0(4) . . ?
C28 C29 C34 112.5(3) . . ?
C30 C29 H29 107.3 . . ?
C28 C29 H29 107.3 . . ?
C34 C29 H29 107.3 . . ?
O7 C19 O6 104.1(3) . . ?
O7 C19 C32 109.3(3) . . ?
O6 C19 C32 108.0(3) . . ?
O7 C19 C33 112.4(4) . . ?
O6 C19 C33 110.8(4) . . ?
C32 C19 C33 111.9(3) . . ?
C19 C32 H32A 109.5 . . ?
C19 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C19 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C29 C34 H34A 109.5 . . ?
C29 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C29 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C19 C33 H33A 109.5 . . ?
C19 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C19 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C26 C27 C28 104.4(4) . . ?
C26 C27 H27A 110.9 . . ?
C28 C27 H27A 110.9 . . ?
C26 C27 H27B 110.9 . . ?
C28 C27 H27B 110.9 . . ?
H27A C27 H27B 108.9 . . ?
C27 C26 C25 102.7(3) . . ?
C27 C26 H26A 111.2 . . ?
C25 C26 H26A 111.2 . . ?
C27 C26 H26B 111.2 . . ?
C25 C26 H26B 111.2 . . ?
H26A C26 H26B 109.1 . . ?
C43 C42 C41 105.7(3) . . ?
C43 C42 H42A 110.6 . . ?
C41 C42 H42A 110.6 . . ?
C43 C42 H42B 110.6 . . ?
C41 C42 H42B 110.6 . . ?
H42A C42 H42B 108.7 . . ?
C44 C43 C42 102.1(3) . . ?
C44 C43 H43A 111.4 . . ?
C42 C43 H43A 111.4 . . ?
C44 C43 H43B 111.4 . . ?
C42 C43 H43B 111.4 . . ?
H43A C43 H43B 109.2 . . ?
C43 C44 C45 104.3(4) . . ?
C43 C44 H44A 110.9 . . ?
C45 C44 H44A 110.9 . . ?
C43 C44 H44B 110.9 . . ?
C45 C44 H44B 110.9 . . ?
H44A C44 H44B 108.9 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Absolute ethanol'
