# 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_xb8331_0m
_database_code_depnum_ccdc_archive 'CCDC 1447407'
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 F O4'
_chemical_formula_weight         240.22

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   5.059(5)
_cell_length_b                   10.704(12)
_cell_length_c                   11.363(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.62(2)
_cell_angle_gamma                90.00
_cell_volume                     602.6(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    384
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      17.84

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_T_max  0.9865
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2945
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.1218
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.08
_reflns_number_total             2093
_reflns_number_gt                1057
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0700P)²+0.0000P] 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       0.036(9)
_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(3)
_refine_ls_number_reflns         2093
_refine_ls_number_parameters     157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1627
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
F1 F 0.3210(9) 0.7545(5) 1.3469(4) 0.0942(17) Uani 1 1 d . . .
O1 O 0.8529(10) 0.9672(5) 0.9354(5) 0.0743(16) Uani 1 1 d . . .
O2 O 1.3191(9) 0.7139(4) 0.7944(4) 0.0589(14) Uani 1 1 d . . .
H2 H 1.4510 0.7447 0.7737 0.088 Uiso 1 1 calc R . .
O3 O 0.7179(10) 0.8086(6) 0.6865(4) 0.0783(17) Uani 1 1 d . . .
O4 O 1.0569(8) 0.9223(4) 0.6455(4) 0.0610(14) Uani 1 1 d . . .
C1 C 0.7262(14) 0.7087(6) 1.1221(6) 0.0566(19) Uani 1 1 d . . .
H1 H 0.8162 0.6446 1.0913 0.068 Uiso 1 1 calc R . .
C2 C 0.5922(14) 0.6851(7) 1.2142(6) 0.061(2) Uani 1 1 d . . .
H2A H 0.5992 0.6058 1.2480 0.073 Uiso 1 1 calc R . .
C3 C 0.4501(16) 0.7770(8) 1.2558(6) 0.068(2) Uani 1 1 d . . .
C4 C 0.4479(16) 0.8989(7) 1.2129(7) 0.070(2) Uani 1 1 d . . .
H4 H 0.3580 0.9619 1.2453 0.085 Uiso 1 1 calc R . .
C5 C 0.5812(13) 0.9240(7) 1.1218(6) 0.0520(18) Uani 1 1 d . . .
H5 H 0.5763 1.0043 1.0902 0.062 Uiso 1 1 calc R . .
C6 C 0.7258(12) 0.8294(6) 1.0755(5) 0.0456(16) Uani 1 1 d . . .
C7 C 0.8602(13) 0.8612(6) 0.9757(6) 0.0478(17) Uani 1 1 d . . .
C8 C 1.0246(12) 0.7610(6) 0.9244(6) 0.0471(17) Uani 1 1 d . . .
H8A H 1.1649 0.7293 0.9885 0.057 Uiso 1 1 calc R . .
H8B H 0.9068 0.6918 0.8937 0.057 Uiso 1 1 calc R . .
C9 C 1.1518(12) 0.8114(6) 0.8254(5) 0.0446(16) Uani 1 1 d . . .
H9 H 1.2640 0.8838 0.8551 0.053 Uiso 1 1 calc R . .
C10 C 0.9492(15) 0.8481(6) 0.7132(6) 0.0523(17) Uani 1 1 d . . .
C11 C 0.8891(17) 0.9574(10) 0.5287(7) 0.092(3) Uani 1 1 d . . .
H11A H 0.7244 0.9976 0.5404 0.110 Uiso 1 1 calc R . .
H11B H 0.8410 0.8837 0.4794 0.110 Uiso 1 1 calc R . .
C12 C 1.049(2) 1.0447(11) 0.4691(7) 0.114(4) Uani 1 1 d . . .
H12A H 0.9617 1.1248 0.4595 0.170 Uiso 1 1 calc R . .
H12B H 1.0617 1.0123 0.3917 0.170 Uiso 1 1 calc R . .
H12C H 1.2268 1.0535 0.5176 0.170 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
F1 C3 1.352(8) . ?
O1 C7 1.221(7) . ?
O2 C9 1.431(7) . ?
O2 H2 0.8200 . ?
O3 C10 1.223(8) . ?
O4 C10 1.300(7) . ?
O4 C11 1.473(8) . ?
C1 C2 1.379(9) . ?
C1 C6 1.396(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.392(10) . ?
C4 C5 1.371(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.475(9) . ?
C7 C8 1.542(8) . ?
C8 C9 1.505(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.517(8) . ?
C9 H9 0.9800 . ?
C11 C12 1.485(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C9 O2 H2 109.5 . . ?
C10 O4 C11 117.1(6) . . ?
C2 C1 C6 119.6(7) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C3 C2 C1 120.5(7) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
F1 C3 C2 120.6(7) . . ?
F1 C3 C4 117.6(7) . . ?
C2 C3 C4 121.6(7) . . ?
C5 C4 C3 118.5(7) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 120.8(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.9(6) . . ?
C1 C6 C7 122.7(6) . . ?
C5 C6 C7 118.4(6) . . ?
O1 C7 C6 121.3(6) . . ?
O1 C7 C8 118.9(6) . . ?
C6 C7 C8 119.8(6) . . ?
C9 C8 C7 112.2(5) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O2 C9 C8 106.6(5) . . ?
O2 C9 C10 108.3(5) . . ?
C8 C9 C10 113.8(5) . . ?
O2 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
O3 C10 O4 124.0(6) . . ?
O3 C10 C9 124.7(6) . . ?
O4 C10 C9 111.3(6) . . ?
O4 C11 C12 107.7(6) . . ?
O4 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C6 C1 C2 C3 3.0(10) . . . . ?
C1 C2 C3 F1 -179.3(6) . . . . ?
C1 C2 C3 C4 -4.0(11) . . . . ?
F1 C3 C4 C5 179.0(7) . . . . ?
C2 C3 C4 C5 3.6(11) . . . . ?
C3 C4 C5 C6 -2.3(11) . . . . ?
C2 C1 C6 C5 -1.7(9) . . . . ?
C2 C1 C6 C7 -178.8(6) . . . . ?
C4 C5 C6 C1 1.4(10) . . . . ?
C4 C5 C6 C7 178.6(6) . . . . ?
C1 C6 C7 O1 178.8(7) . . . . ?
C5 C6 C7 O1 1.7(10) . . . . ?
C1 C6 C7 C8 -4.1(9) . . . . ?
C5 C6 C7 C8 178.8(6) . . . . ?
O1 C7 C8 C9 -1.4(8) . . . . ?
C6 C7 C8 C9 -178.6(5) . . . . ?
C7 C8 C9 O2 174.2(5) . . . . ?
C7 C8 C9 C10 -66.4(7) . . . . ?
C11 O4 C10 O3 -1.6(10) . . . . ?
C11 O4 C10 C9 175.2(6) . . . . ?
O2 C9 C10 O3 96.7(8) . . . . ?
C8 C9 C10 O3 -21.6(9) . . . . ?
O2 C9 C10 O4 -80.0(6) . . . . ?
C8 C9 C10 O4 161.6(6) . . . . ?
C10 O4 C11 C12 178.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_xb8523_0m
_database_code_depnum_ccdc_archive 'CCDC 1447408'
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 O5'
_chemical_formula_weight         252.26

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   P2(1)

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

_cell_length_a                   5.0181(11)
_cell_length_b                   11.253(2)
_cell_length_c                   22.901(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.618(4)
_cell_angle_gamma                90.00
_cell_volume                     1293.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1167
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      21.16

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9860
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6419
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         0.89
_diffrn_reflns_theta_max         25.10
_reflns_number_total             4112
_reflns_number_gt                2710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0525P)²+0.0913P] 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       0.0127(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   0.9(14)
_refine_ls_number_reflns         4112
_refine_ls_number_parameters     331
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.6972(6) 0.6430(3) 1.13319(12) 0.0838(9) Uani 1 1 d . . .
O2 O -0.0194(5) 0.4730(2) 0.92255(12) 0.0800(9) Uani 1 1 d . . .
O3 O -0.5432(5) 0.7218(3) 0.85863(13) 0.0820(9) Uani 1 1 d . . .
H3 H -0.6863 0.6959 0.8466 0.123 Uiso 1 1 calc R . .
O4 O -0.3452(5) 0.5140(3) 0.78775(11) 0.0804(9) Uani 1 1 d . . .
O5 O -0.0055(5) 0.6326(3) 0.80728(11) 0.0872(10) Uani 1 1 d . . .
O6 O 1.2397(6) 0.6254(2) 0.64107(11) 0.0792(8) Uani 1 1 d . . .
O7 O 0.5117(6) 0.4451(2) 0.43407(12) 0.0794(9) Uani 1 1 d . . .
O8 O -0.0218(5) 0.6898(3) 0.37119(13) 0.0803(9) Uani 1 1 d . . .
H8 H -0.1453 0.6640 0.3512 0.120 Uiso 1 1 calc R . .
O9 O 0.1665(5) 0.4901(3) 0.29733(13) 0.1090(13) Uani 1 1 d . . .
O10 O 0.5200(5) 0.6002(3) 0.31742(11) 0.0838(9) Uani 1 1 d . . .
C1 C 0.7251(10) 0.7545(4) 1.1623(2) 0.1025(16) Uani 1 1 d . . .
H1A H 0.7904 0.8128 1.1354 0.154 Uiso 1 1 calc R . .
H1B H 0.8486 0.7465 1.1943 0.154 Uiso 1 1 calc R . .
H1C H 0.5550 0.7793 1.1767 0.154 Uiso 1 1 calc R . .
C2 C 0.5217(7) 0.6348(3) 1.08856(16) 0.0616(10) Uani 1 1 d . . .
C3 C 0.3612(7) 0.7248(3) 1.06843(16) 0.0625(10) Uani 1 1 d . . .
H3A H 0.3690 0.7994 1.0858 0.075 Uiso 1 1 calc R . .
C4 C 0.1877(7) 0.7045(3) 1.02221(15) 0.0575(10) Uani 1 1 d . . .
H4 H 0.0797 0.7662 1.0089 0.069 Uiso 1 1 calc R . .
C5 C 0.1704(6) 0.5952(3) 0.99530(14) 0.0517(9) Uani 1 1 d . . .
C6 C 0.3353(7) 0.5043(3) 1.01626(17) 0.0649(11) Uani 1 1 d . . .
H6 H 0.3274 0.4297 0.9989 0.078 Uiso 1 1 calc R . .
C7 C 0.5077(8) 0.5231(4) 1.06176(17) 0.0682(11) Uani 1 1 d . . .
H7 H 0.6163 0.4616 1.0750 0.082 Uiso 1 1 calc R . .
C8 C -0.0130(7) 0.5702(3) 0.94584(15) 0.0572(10) Uani 1 1 d . . .
C9 C -0.1954(7) 0.6684(3) 0.92330(15) 0.0588(10) Uani 1 1 d . . .
H9A H -0.3055 0.6968 0.9550 0.071 Uiso 1 1 calc R . .
H9B H -0.0881 0.7345 0.9099 0.071 Uiso 1 1 calc R . .
C10 C -0.3731(7) 0.6256(3) 0.87369(15) 0.0590(10) Uani 1 1 d . . .
H10 H -0.4798 0.5578 0.8867 0.071 Uiso 1 1 calc R . .
C11 C -0.2156(7) 0.5912(4) 0.82075(16) 0.0636(10) Uani 1 1 d . . .
C12 C -0.2225(10) 0.4806(6) 0.73272(18) 0.1092(18) Uani 1 1 d . . .
H12A H -0.2005 0.5506 0.7085 0.131 Uiso 1 1 calc R . .
H12B H -0.0476 0.4469 0.7403 0.131 Uiso 1 1 calc R . .
C13 C -0.3813(13) 0.3976(5) 0.7032(2) 0.137(2) Uani 1 1 d . . .
H13A H -0.3723 0.3226 0.7232 0.205 Uiso 1 1 calc R . .
H13B H -0.3183 0.3881 0.6641 0.205 Uiso 1 1 calc R . .
H13C H -0.5626 0.4249 0.7022 0.205 Uiso 1 1 calc R . .
C14 C 1.2651(10) 0.7386(4) 0.66856(18) 0.0951(15) Uani 1 1 d . . .
H14A H 1.3228 0.7962 0.6405 0.143 Uiso 1 1 calc R . .
H14B H 1.3936 0.7336 0.6998 0.143 Uiso 1 1 calc R . .
H14C H 1.0958 0.7621 0.6839 0.143 Uiso 1 1 calc R . .
C15 C 1.0603(7) 0.6141(4) 0.59658(15) 0.0599(10) Uani 1 1 d . . .
C16 C 0.8978(7) 0.7041(3) 0.57650(16) 0.0602(10) Uani 1 1 d . . .
H16 H 0.9068 0.7794 0.5932 0.072 Uiso 1 1 calc R . .
C17 C 0.7206(7) 0.6812(3) 0.53112(15) 0.0578(10) Uani 1 1 d . . .
H17 H 0.6111 0.7421 0.5175 0.069 Uiso 1 1 calc R . .
C18 C 0.7023(7) 0.5697(3) 0.50544(14) 0.0525(9) Uani 1 1 d . . .
C19 C 0.8693(7) 0.4808(3) 0.52666(16) 0.0622(10) Uani 1 1 d . . .
H19 H 0.8614 0.4054 0.5101 0.075 Uiso 1 1 calc R . .
C20 C 1.0459(8) 0.5025(3) 0.57170(17) 0.0687(11) Uani 1 1 d . . .
H20 H 1.1559 0.4419 0.5854 0.082 Uiso 1 1 calc R . .
C21 C 0.5166(7) 0.5436(3) 0.45636(16) 0.0585(10) Uani 1 1 d . . .
C22 C 0.3354(7) 0.6388(3) 0.43375(15) 0.0598(10) Uani 1 1 d . . .
H22A H 0.4420 0.7046 0.4198 0.072 Uiso 1 1 calc R . .
H22B H 0.2270 0.6679 0.4655 0.072 Uiso 1 1 calc R . .
C23 C 0.1556(7) 0.5964(3) 0.38510(15) 0.0626(10) Uani 1 1 d . . .
H23 H 0.0537 0.5275 0.3985 0.075 Uiso 1 1 calc R . .
C24 C 0.3059(7) 0.5633(4) 0.33099(17) 0.0657(11) Uani 1 1 d . . .
C25 C 0.2743(10) 0.4611(8) 0.2400(2) 0.161(3) Uani 1 1 d . . .
H25A H 0.3974 0.5232 0.2287 0.193 Uiso 1 1 calc R . .
H25B H 0.3746 0.3876 0.2431 0.193 Uiso 1 1 calc R . .
C26 C 0.0970(13) 0.4493(7) 0.1995(2) 0.158(3) Uani 1 1 d . . .
H26A H 0.1824 0.4314 0.1633 0.237 Uiso 1 1 calc R . .
H26B H -0.0020 0.5219 0.1956 0.237 Uiso 1 1 calc R . .
H26C H -0.0220 0.3858 0.2095 0.237 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 1.345(4) . ?
O1 C1 1.427(5) . ?
O2 C8 1.217(4) . ?
O3 C10 1.418(4) . ?
O3 H3 0.8200 . ?
O4 C11 1.318(4) . ?
O4 C12 1.458(4) . ?
O5 C11 1.196(4) . ?
O6 C15 1.358(4) . ?
O6 C14 1.425(5) . ?
O7 C21 1.221(4) . ?
O8 C23 1.412(4) . ?
O8 H8 0.8200 . ?
O9 C24 1.323(4) . ?
O9 C25 1.463(5) . ?
O10 C24 1.196(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.370(5) . ?
C2 C7 1.400(5) . ?
C3 C4 1.382(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(5) . ?
C5 C8 1.479(5) . ?
C6 C7 1.364(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.522(5) . ?
C9 C10 1.515(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.505(5) . ?
C10 H10 0.9800 . ?
C12 C13 1.397(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.377(5) . ?
C15 C20 1.380(5) . ?
C16 C17 1.385(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(5) . ?
C18 C21 1.482(5) . ?
C19 C20 1.375(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.494(5) . ?
C22 C23 1.504(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.504(5) . ?
C23 H23 0.9800 . ?
C25 C26 1.284(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C2 O1 C1 118.4(3) . . ?
C10 O3 H3 109.5 . . ?
C11 O4 C12 117.1(3) . . ?
C15 O6 C14 118.1(3) . . ?
C23 O8 H8 109.5 . . ?
C24 O9 C25 117.6(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.6(4) . . ?
O1 C2 C7 115.1(3) . . ?
C3 C2 C7 119.3(4) . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 117.7(3) . . ?
C4 C5 C8 123.2(3) . . ?
C6 C5 C8 119.0(3) . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 120.2(4) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
O2 C8 C5 121.3(4) . . ?
O2 C8 C9 119.4(3) . . ?
C5 C8 C9 119.3(3) . . ?
C10 C9 C8 111.7(3) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
O3 C10 C11 108.7(3) . . ?
O3 C10 C9 106.7(3) . . ?
C11 C10 C9 112.1(3) . . ?
O3 C10 H10 109.8 . . ?
C11 C10 H10 109.8 . . ?
C9 C10 H10 109.8 . . ?
O5 C11 O4 122.7(4) . . ?
O5 C11 C10 125.4(4) . . ?
O4 C11 C10 111.8(3) . . ?
C13 C12 O4 110.2(4) . . ?
C13 C12 H12A 109.6 . . ?
O4 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
O4 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
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 . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C15 C16 124.5(4) . . ?
O6 C15 C20 115.2(4) . . ?
C16 C15 C20 120.2(4) . . ?
C15 C16 C17 119.1(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 121.7(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C19 117.8(3) . . ?
C17 C18 C21 122.6(3) . . ?
C19 C18 C21 119.6(3) . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C15 120.1(4) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
O7 C21 C18 120.4(4) . . ?
O7 C21 C22 119.8(4) . . ?
C18 C21 C22 119.8(3) . . ?
C21 C22 C23 112.8(3) . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
O8 C23 C22 107.6(3) . . ?
O8 C23 C24 108.6(3) . . ?
C22 C23 C24 112.8(3) . . ?
O8 C23 H23 109.3 . . ?
C22 C23 H23 109.3 . . ?
C24 C23 H23 109.3 . . ?
O10 C24 O9 122.4(4) . . ?
O10 C24 C23 126.0(4) . . ?
O9 C24 C23 111.6(3) . . ?
C26 C25 O9 114.2(5) . . ?
C26 C25 H25A 108.7 . . ?
O9 C25 H25A 108.7 . . ?
C26 C25 H25B 108.7 . . ?
O9 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C1 O1 C2 C3 -0.9(6) . . . . ?
C1 O1 C2 C7 179.3(4) . . . . ?
O1 C2 C3 C4 -179.7(3) . . . . ?
C7 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C3 C4 C5 C8 179.9(3) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C8 C5 C6 C7 180.0(3) . . . . ?
C5 C6 C7 C2 0.2(5) . . . . ?
O1 C2 C7 C6 179.6(3) . . . . ?
C3 C2 C7 C6 -0.2(6) . . . . ?
C4 C5 C8 O2 178.7(3) . . . . ?
C6 C5 C8 O2 -1.3(5) . . . . ?
C4 C5 C8 C9 -0.7(5) . . . . ?
C6 C5 C8 C9 179.3(3) . . . . ?
O2 C8 C9 C10 2.0(4) . . . . ?
C5 C8 C9 C10 -178.6(3) . . . . ?
C8 C9 C10 O3 176.8(3) . . . . ?
C8 C9 C10 C11 -64.4(4) . . . . ?
C12 O4 C11 O5 -0.6(6) . . . . ?
C12 O4 C11 C10 175.4(4) . . . . ?
O3 C10 C11 O5 88.8(4) . . . . ?
C9 C10 C11 O5 -28.8(5) . . . . ?
O3 C10 C11 O4 -86.9(4) . . . . ?
C9 C10 C11 O4 155.4(3) . . . . ?
C11 O4 C12 C13 179.3(5) . . . . ?
C14 O6 C15 C16 -0.9(5) . . . . ?
C14 O6 C15 C20 179.8(4) . . . . ?
O6 C15 C16 C17 -179.4(3) . . . . ?
C20 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C16 C17 C18 C21 -179.2(3) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
C21 C18 C19 C20 179.3(3) . . . . ?
C18 C19 C20 C15 -0.2(6) . . . . ?
O6 C15 C20 C19 179.4(3) . . . . ?
C16 C15 C20 C19 0.1(6) . . . . ?
C17 C18 C21 O7 178.1(3) . . . . ?
C19 C18 C21 O7 -0.9(5) . . . . ?
C17 C18 C21 C22 -1.4(5) . . . . ?
C19 C18 C21 C22 179.6(3) . . . . ?
O7 C21 C22 C23 1.9(5) . . . . ?
C18 C21 C22 C23 -178.5(3) . . . . ?
C21 C22 C23 O8 174.6(3) . . . . ?
C21 C22 C23 C24 -65.6(4) . . . . ?
C25 O9 C24 O10 -4.2(7) . . . . ?
C25 O9 C24 C23 173.1(5) . . . . ?
O8 C23 C24 O10 94.6(5) . . . . ?
C22 C23 C24 O10 -24.6(6) . . . . ?
O8 C23 C24 O9 -82.6(4) . . . . ?
C22 C23 C24 O9 158.2(3) . . . . ?
C24 O9 C25 C26 -143.8(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.047
