# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1435614'
_audit_update_record             
;
2015-11-07 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18.67 H16 O8'
_chemical_formula_weight         368.31

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.8293(4)
_cell_length_b                   19.0054(6)
_cell_length_c                   6.7783(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1266.25(10)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.976
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6961
_exptl_absorpt_correction_T_max  0.8287
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Xcalibur
_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            8689
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.65
_diffrn_reflns_theta_max         66.69
_reflns_number_total             2216
_reflns_number_gt                2015
_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)+(0.0930P)²+0.5740P] 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   0.0(4)
_refine_ls_number_reflns         2216
_refine_ls_number_parameters     195
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1511
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.067
_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
C1 C -0.7355(3) -0.03026(12) -0.0367(4) 0.0338(6) Uani 1 1 d . . .
O2 O -0.76229(18) -0.15649(8) -0.0371(3) 0.0391(5) Uani 1 1 d . . .
O3 O -0.5116(2) 0.02193(10) -0.0503(4) 0.0488(5) Uani 1 1 d . . .
H3 H -0.4911 -0.0198 -0.0428 0.073 Uiso 1 1 calc R . .
O4 O -0.55507(18) -0.11350(9) -0.0463(3) 0.0439(5) Uani 1 1 d . . .
C5 C -0.9003(3) -0.14531(13) -0.0248(5) 0.0403(6) Uani 1 1 d . A .
C6 C -0.6774(3) -0.09996(12) -0.0398(4) 0.0339(6) Uani 1 1 d . . .
C7 C -0.7001(4) 0.09598(14) -0.0384(5) 0.0487(8) Uani 1 1 d . . .
H7 H -0.6426 0.1348 -0.0410 0.058 Uiso 1 1 calc R . .
C8 C -0.8772(3) -0.01953(13) -0.0277(4) 0.0375(6) Uani 1 1 d . . .
C9 C -0.9288(3) 0.04852(14) -0.0257(5) 0.0481(7) Uani 1 1 d . . .
H9 H -1.0223 0.0559 -0.0209 0.058 Uiso 1 1 calc R . .
C10 C -0.9602(3) -0.08241(14) -0.0198(5) 0.0428(7) Uani 1 1 d . A .
C11 C -0.6465(3) 0.02860(14) -0.0422(4) 0.0394(6) Uani 1 1 d . . .
O12 O -0.8961(3) 0.17073(11) -0.0279(5) 0.0801(9) Uani 1 1 d . . .
H12 H -0.8356 0.2003 -0.0363 0.120 Uiso 1 1 calc R . .
O13 O -0.9580(3) -0.25329(12) 0.1327(4) 0.0679(8) Uani 1 1 d . A .
H13 H -0.9826 -0.2932 0.1036 0.102 Uiso 1 1 calc R . .
C14 C -0.8404(4) 0.10535(14) -0.0309(5) 0.0528(8) Uani 1 1 d . . .
C15 C -0.9948(3) -0.20674(16) -0.0180(6) 0.0567(9) Uani 1 1 d . . .
H15 H -1.0097 -0.2294 -0.1461 0.068 Uiso 0.676(12) 1 calc PR A 1
H15A H -0.9650 -0.2331 -0.1345 0.068 Uiso 0.324(12) 1 calc PR A 2
C16 C -1.1125(3) -0.09136(19) -0.0012(6) 0.0597(10) Uani 1 1 d . . .
H16 H -1.1394 -0.0617 0.1104 0.072 Uiso 0.676(12) 1 calc PR A 1
H16A H -1.1516 -0.0829 0.1297 0.072 Uiso 0.324(12) 1 calc PR A 2
C18 C -1.1929(4) -0.0647(2) -0.1742(7) 0.0701(11) Uani 1 1 d . A .
H18A H -1.1855 -0.0143 -0.1810 0.105 Uiso 1 1 calc R . .
H18B H -1.2867 -0.0776 -0.1588 0.105 Uiso 1 1 calc R . .
H18C H -1.1579 -0.0850 -0.2936 0.105 Uiso 1 1 calc R . .
C19 C -1.1292(5) -0.1662(3) 0.0700(10) 0.057(2) Uani 0.676(12) 1 d P A 1
H19A H -1.2124 -0.1868 0.0190 0.069 Uiso 0.676(12) 1 calc PR A 1
H19B H -1.1310 -0.1682 0.2130 0.069 Uiso 0.676(12) 1 calc PR A 1
C21 C -1.1165(10) -0.1783(5) -0.0863(17) 0.045(3) Uani 0.324(12) 1 d P A 2
H21A H -1.1940 -0.2034 -0.0326 0.054 Uiso 0.324(12) 1 calc PR A 2
H21B H -1.1208 -0.1798 -0.2292 0.054 Uiso 0.324(12) 1 calc PR A 2
O17 O -0.7131(9) -0.73141(18) -0.0642(9) 0.197(4) Uani 1 1 d U . .
C2 C -0.7009(12) -0.7076(9) 0.022(2) 0.317(12) Uani 1 1 d U . .


_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
C1 C8 1.409(4) . ?
C1 C11 1.421(4) . ?
C1 C6 1.443(3) . ?
O2 C6 1.361(3) . ?
O2 C5 1.376(3) . ?
O3 C11 1.334(4) . ?
O4 C6 1.230(3) . ?
C5 C10 1.333(4) . ?
C5 C15 1.493(4) . ?
C7 C11 1.385(4) . ?
C7 C14 1.391(5) . ?
C8 C9 1.389(3) . ?
C8 C10 1.448(4) . ?
C9 C14 1.387(5) . ?
C10 C16 1.512(4) . ?
O12 C14 1.358(3) . ?
O13 C15 1.399(4) . ?
C15 C21 1.392(10) . ?
C15 C19 1.642(6) . ?
C16 C18 1.503(5) . ?
C16 C19 1.511(6) . ?
C16 C21 1.750(11) . ?
O17 C2 0.750(19) . ?

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
C8 C1 C11 119.7(2) . . ?
C8 C1 C6 121.7(2) . . ?
C11 C1 C6 118.6(2) . . ?
C6 O2 C5 118.93(19) . . ?
C10 C5 O2 125.1(2) . . ?
C10 C5 C15 115.2(2) . . ?
O2 C5 C15 119.7(2) . . ?
O4 C6 O2 115.8(2) . . ?
O4 C6 C1 125.4(2) . . ?
O2 C6 C1 118.8(2) . . ?
C11 C7 C14 119.8(3) . . ?
C9 C8 C1 119.7(3) . . ?
C9 C8 C10 124.2(3) . . ?
C1 C8 C10 116.0(2) . . ?
C14 C9 C8 119.8(3) . . ?
C5 C10 C8 119.4(2) . . ?
C5 C10 C16 109.8(3) . . ?
C8 C10 C16 130.8(3) . . ?
O3 C11 C7 117.8(3) . . ?
O3 C11 C1 122.6(2) . . ?
C7 C11 C1 119.5(3) . . ?
O12 C14 C9 117.4(3) . . ?
O12 C14 C7 121.1(3) . . ?
C9 C14 C7 121.5(3) . . ?
C21 C15 O13 135.3(5) . . ?
C21 C15 C5 102.7(4) . . ?
O13 C15 C5 110.9(3) . . ?
C21 C15 C19 41.2(5) . . ?
O13 C15 C19 103.9(4) . . ?
C5 C15 C19 98.3(3) . . ?
C18 C16 C19 120.7(4) . . ?
C18 C16 C10 114.7(3) . . ?
C19 C16 C10 103.9(3) . . ?
C18 C16 C21 92.8(4) . . ?
C19 C16 C21 38.2(4) . . ?
C10 C16 C21 95.8(4) . . ?
C16 C19 C15 103.8(3) . . ?
C15 C21 C16 103.8(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
C6 O2 C5 C10 1.7(5) . . . . ?
C6 O2 C5 C15 -178.9(3) . . . . ?
C5 O2 C6 O4 178.4(3) . . . . ?
C5 O2 C6 C1 -2.2(4) . . . . ?
C8 C1 C6 O4 -179.5(3) . . . . ?
C11 C1 C6 O4 0.2(5) . . . . ?
C8 C1 C6 O2 1.1(4) . . . . ?
C11 C1 C6 O2 -179.2(2) . . . . ?
C11 C1 C8 C9 0.5(4) . . . . ?
C6 C1 C8 C9 -179.8(3) . . . . ?
C11 C1 C8 C10 -179.2(3) . . . . ?
C6 C1 C8 C10 0.5(4) . . . . ?
C1 C8 C9 C14 -0.6(5) . . . . ?
C10 C8 C9 C14 179.1(3) . . . . ?
O2 C5 C10 C8 0.1(5) . . . . ?
C15 C5 C10 C8 -179.4(3) . . . . ?
O2 C5 C10 C16 -178.6(3) . . . . ?
C15 C5 C10 C16 1.9(5) . . . . ?
C9 C8 C10 C5 179.2(3) . . . . ?
C1 C8 C10 C5 -1.1(4) . . . . ?
C9 C8 C10 C16 -2.4(6) . . . . ?
C1 C8 C10 C16 177.3(3) . . . . ?
C14 C7 C11 O3 179.7(3) . . . . ?
C14 C7 C11 C1 -0.5(5) . . . . ?
C8 C1 C11 O3 179.8(3) . . . . ?
C6 C1 C11 O3 0.1(4) . . . . ?
C8 C1 C11 C7 0.0(4) . . . . ?
C6 C1 C11 C7 -179.7(3) . . . . ?
C8 C9 C14 O12 -179.8(3) . . . . ?
C8 C9 C14 C7 0.1(5) . . . . ?
C11 C7 C14 O12 -179.7(3) . . . . ?
C11 C7 C14 C9 0.4(5) . . . . ?
C10 C5 C15 C21 22.9(7) . . . . ?
O2 C5 C15 C21 -156.6(6) . . . . ?
C10 C5 C15 O13 -127.2(3) . . . . ?
O2 C5 C15 O13 53.3(4) . . . . ?
C10 C5 C15 C19 -18.8(5) . . . . ?
O2 C5 C15 C19 161.7(4) . . . . ?
C5 C10 C16 C18 -115.9(4) . . . . ?
C8 C10 C16 C18 65.6(5) . . . . ?
C5 C10 C16 C19 17.9(5) . . . . ?
C8 C10 C16 C19 -160.6(4) . . . . ?
C5 C10 C16 C21 -20.1(5) . . . . ?
C8 C10 C16 C21 161.4(5) . . . . ?
C18 C16 C19 C15 102.2(4) . . . . ?
C10 C16 C19 C15 -28.1(5) . . . . ?
C21 C16 C19 C15 53.5(6) . . . . ?
C21 C15 C19 C16 -71.8(7) . . . . ?
O13 C15 C19 C16 142.0(4) . . . . ?
C5 C15 C19 C16 28.0(5) . . . . ?
O13 C15 C21 C16 105.4(6) . . . . ?
C5 C15 C21 C16 -33.0(7) . . . . ?
C19 C15 C21 C16 55.1(6) . . . . ?
C18 C16 C21 C15 148.9(6) . . . . ?
C19 C16 C21 C15 -71.4(7) . . . . ?
C10 C16 C21 C15 33.8(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        66.69
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_fsgfsgf
_database_code_depnum_ccdc_archive 'CCDC 1435618'
_audit_update_record             
;
2015-11-07 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 O6'
_chemical_formula_weight         276.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.2401(3)
_cell_length_b                   12.8808(5)
_cell_length_c                   10.0633(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.788(3)
_cell_angle_gamma                90
_cell_volume                     1195.12(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.034
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4796
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.586
_diffrn_reflns_theta_max         66.769
_diffrn_reflns_theta_full        66.769
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2085
_reflns_number_gt                1751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.7449P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2085
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.15892(17) 1.03458(11) 0.99691(15) 0.0238(4) Uani 1 1 d . . . . .
H2 H 0.1317 1.0647 0.9280 0.036 Uiso 1 1 calc R U . . .
O6 O 0.12453(16) 0.92785(11) 0.60331(14) 0.0220(4) Uani 1 1 d . . . . .
O1 O 0.08989(17) 1.05373(11) 0.74417(15) 0.0251(4) Uani 1 1 d . . . . .
O4 O 0.05638(17) 0.57651(12) 0.69618(14) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.0306 0.5311 0.6426 0.038 Uiso 1 1 calc R U . . .
O3 O 0.02334(16) 0.60693(12) 0.40768(14) 0.0243(4) Uani 1 1 d . . . . .
O5 O 0.25630(18) 0.70336(12) 1.16715(14) 0.0269(4) Uani 1 1 d . . . . .
C7 C 0.1601(2) 0.89256(16) 0.8403(2) 0.0175(4) Uani 1 1 d . . . . .
C26 C 0.2004(2) 0.71753(16) 0.9283(2) 0.0186(5) Uani 1 1 d . . . . .
H26 H 0.2055 0.6462 0.9151 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2215(2) 0.76015(17) 1.05600(19) 0.0192(5) Uani 1 1 d . . . . .
C10 C 0.1751(2) 0.93230(16) 0.9716(2) 0.0186(5) Uani 1 1 d . . . . .
C11 C 0.1718(2) 0.78425(16) 0.8221(2) 0.0175(4) Uani 1 1 d . . . . .
C12 C 0.2078(2) 0.86622(17) 1.0771(2) 0.0214(5) Uani 1 1 d . . . . .
H12 H 0.2208 0.8928 1.1629 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1237(2) 0.96265(16) 0.7292(2) 0.0188(5) Uani 1 1 d . . . . .
C14 C 0.0720(2) 0.67330(17) 0.4846(2) 0.0192(5) Uani 1 1 d . . . . .
C15 C 0.0930(2) 0.66191(16) 0.6304(2) 0.0190(5) Uani 1 1 d . . . . .
C16 C 0.1176(2) 0.78147(17) 0.4489(2) 0.0217(5) Uani 1 1 d . . . . .
H16A H 0.0344 0.8228 0.4178 0.026 Uiso 1 1 calc R U . . .
H16B H 0.1863 0.7798 0.3800 0.026 Uiso 1 1 calc R U . . .
C17 C 0.2588(3) 0.59292(18) 1.1565(2) 0.0271(5) Uani 1 1 d . . . . .
H17A H 0.1639 0.5683 1.1275 0.041 Uiso 1 1 calc R U . . .
H17B H 0.2874 0.5634 1.2419 0.041 Uiso 1 1 calc R U . . .
H17C H 0.3268 0.5728 1.0932 0.041 Uiso 1 1 calc R U . . .
C18 C 0.1493(2) 0.74984(16) 0.68424(19) 0.0181(5) Uani 1 1 d . . . . .
C19 C 0.3516(2) 0.84019(19) 0.5747(2) 0.0263(5) Uani 1 1 d . . . . .
H19A H 0.3709 0.8919 0.5095 0.039 Uiso 1 1 calc R U . . .
H19B H 0.3954 0.7757 0.5515 0.039 Uiso 1 1 calc R U . . .
H19C H 0.3913 0.8623 0.6606 0.039 Uiso 1 1 calc R U . . .
C20 C 0.1882(2) 0.82555(16) 0.5787(2) 0.0197(5) Uani 1 1 d . . . . .


_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
O2 C10 1.352(2) . ?
O2 H2 0.8200 . ?
O6 C13 1.345(3) . ?
O6 C20 1.471(2) . ?
O1 C13 1.226(3) . ?
O4 C15 1.339(2) . ?
O4 H4 0.8200 . ?
O3 C14 1.219(3) . ?
O5 C9 1.357(3) . ?
O5 C17 1.427(3) . ?
C7 C11 1.412(3) . ?
C7 C10 1.415(3) . ?
C7 C13 1.459(3) . ?
C26 C11 1.383(3) . ?
C26 C9 1.399(3) . ?
C26 H26 0.9300 . ?
C9 C12 1.390(3) . ?
C10 C12 1.379(3) . ?
C11 C18 1.458(3) . ?
C12 H12 0.9300 . ?
C14 C15 1.475(3) . ?
C14 C16 1.506(3) . ?
C15 C18 1.345(3) . ?
C16 C20 1.530(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C20 1.503(3) . ?
C19 C20 1.524(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C10 O2 H2 109.5 . . ?
C13 O6 C20 119.00(16) . . ?
C15 O4 H4 109.5 . . ?
C9 O5 C17 118.68(17) . . ?
C11 C7 C10 118.37(18) . . ?
C11 C7 C13 121.84(18) . . ?
C10 C7 C13 119.66(19) . . ?
C11 C26 C9 118.28(19) . . ?
C11 C26 H26 120.9 . . ?
C9 C26 H26 120.9 . . ?
O5 C9 C12 115.04(18) . . ?
O5 C9 C26 123.82(19) . . ?
C12 C9 C26 121.14(19) . . ?
O2 C10 C12 118.53(19) . . ?
O2 C10 C7 121.56(19) . . ?
C12 C10 C7 119.91(19) . . ?
C26 C11 C7 121.72(19) . . ?
C26 C11 C18 123.65(19) . . ?
C7 C11 C18 114.62(18) . . ?
C10 C12 C9 120.47(19) . . ?
C10 C12 H12 119.8 . . ?
C9 C12 H12 119.8 . . ?
O1 C13 O6 116.87(19) . . ?
O1 C13 C7 123.09(19) . . ?
O6 C13 C7 120.03(18) . . ?
O3 C14 C15 125.5(2) . . ?
O3 C14 C16 126.52(18) . . ?
C15 C14 C16 107.98(17) . . ?
O4 C15 C18 126.62(19) . . ?
O4 C15 C14 123.56(18) . . ?
C18 C15 C14 109.80(18) . . ?
C14 C16 C20 104.50(16) . . ?
C14 C16 H16A 110.9 . . ?
C20 C16 H16A 110.9 . . ?
C14 C16 H16B 110.9 . . ?
C20 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 C11 131.76(19) . . ?
C15 C18 C20 111.46(18) . . ?
C11 C18 C20 116.71(18) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C20 C18 110.17(16) . . ?
O6 C20 C19 107.56(17) . . ?
C18 C20 C19 112.48(17) . . ?
O6 C20 C16 108.87(16) . . ?
C18 C20 C16 104.72(17) . . ?
C19 C20 C16 113.00(17) . . ?

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
C17 O5 C9 C12 174.04(19) . . . . ?
C17 O5 C9 C26 -6.0(3) . . . . ?
C11 C26 C9 O5 -177.10(19) . . . . ?
C11 C26 C9 C12 2.8(3) . . . . ?
C11 C7 C10 O2 -177.05(18) . . . . ?
C13 C7 C10 O2 -1.1(3) . . . . ?
C11 C7 C10 C12 3.3(3) . . . . ?
C13 C7 C10 C12 179.23(18) . . . . ?
C9 C26 C11 C7 -1.6(3) . . . . ?
C9 C26 C11 C18 179.32(18) . . . . ?
C10 C7 C11 C26 -1.4(3) . . . . ?
C13 C7 C11 C26 -177.28(19) . . . . ?
C10 C7 C11 C18 177.74(17) . . . . ?
C13 C7 C11 C18 1.9(3) . . . . ?
O2 C10 C12 C9 178.23(18) . . . . ?
C7 C10 C12 C9 -2.1(3) . . . . ?
O5 C9 C12 C10 178.94(18) . . . . ?
C26 C9 C12 C10 -1.0(3) . . . . ?
C20 O6 C13 O1 169.43(18) . . . . ?
C20 O6 C13 C7 -11.4(3) . . . . ?
C11 C7 C13 O1 167.8(2) . . . . ?
C10 C7 C13 O1 -8.0(3) . . . . ?
C11 C7 C13 O6 -11.4(3) . . . . ?
C10 C7 C13 O6 172.84(17) . . . . ?
O3 C14 C15 O4 -1.9(3) . . . . ?
C16 C14 C15 O4 176.70(19) . . . . ?
O3 C14 C15 C18 179.7(2) . . . . ?
C16 C14 C15 C18 -1.7(2) . . . . ?
O3 C14 C16 C20 -172.7(2) . . . . ?
C15 C14 C16 C20 8.7(2) . . . . ?
O4 C15 C18 C11 -8.0(4) . . . . ?
C14 C15 C18 C11 170.4(2) . . . . ?
O4 C15 C18 C20 175.16(19) . . . . ?
C14 C15 C18 C20 -6.5(2) . . . . ?
C26 C11 C18 C15 31.1(4) . . . . ?
C7 C11 C18 C15 -148.1(2) . . . . ?
C26 C11 C18 C20 -152.2(2) . . . . ?
C7 C11 C18 C20 28.7(3) . . . . ?
C13 O6 C20 C18 39.5(2) . . . . ?
C13 O6 C20 C19 -83.4(2) . . . . ?
C13 O6 C20 C16 153.81(17) . . . . ?
C15 C18 C20 O6 128.79(18) . . . . ?
C11 C18 C20 O6 -48.6(2) . . . . ?
C15 C18 C20 C19 -111.2(2) . . . . ?
C11 C18 C20 C19 71.4(2) . . . . ?
C15 C18 C20 C16 11.9(2) . . . . ?
C11 C18 C20 C16 -165.54(17) . . . . ?
C14 C16 C20 O6 -129.78(17) . . . . ?
C14 C16 C20 C18 -12.0(2) . . . . ?
C14 C16 C20 C19 110.8(2) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.076

