# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1500178'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;
_audit_creation_date             2016-08-19
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H12 O4'
_chemical_formula_moiety         'C10 H12 O4'
_chemical_formula_weight         196.20
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.1845(7)
_cell_length_b                   11.6355(15)
_cell_length_c                   16.143(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.867(3)
_cell_angle_gamma                90.0000
_cell_volume                     968.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    818
_cell_measurement_theta_min      18.50
_cell_measurement_theta_max      46.70
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416.00
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.983

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            10037
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_theta_max         68.038
_diffrn_reflns_theta_min         4.693
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1740
_reflns_number_gt                1478
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0928
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1740
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0551P)²+0.1448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.0636(2) 0.94372(9) 0.11596(6) 0.0469(3) Uani 1 1 d D . . . .
H1 H -0.056(4) 1.0009(16) 0.1065(13) 0.082(7) Uiso 1 1 d D . . . .
O2 O -0.20242(19) 1.05116(8) 0.22670(6) 0.0400(3) Uani 1 1 d . . . . .
O9 O -0.0963(2) 0.80904(10) 0.53459(7) 0.0624(3) Uani 1 1 d . . . . .
O10 O -0.2467(2) 0.60593(9) 0.46336(6) 0.0486(3) Uani 1 1 d D . . . .
H10 H -0.272(4) 0.6081(16) 0.5184(10) 0.069(6) Uiso 1 1 d D . . . .
C1 C 0.1162(3) 0.91943(11) 0.19887(8) 0.0357(3) Uani 1 1 d . . . . .
C2 C -0.0211(2) 0.97325(10) 0.25835(8) 0.0332(3) Uani 1 1 d . . . . .
C3 C 0.0333(2) 0.94606(11) 0.34153(8) 0.0347(3) Uani 1 1 d . . . . .
H3 H -0.0610 0.9823 0.3817 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2258(3) 0.86579(11) 0.36726(8) 0.0365(3) Uani 1 1 d . . . . .
C5 C 0.3621(3) 0.81415(12) 0.30803(9) 0.0399(3) Uani 1 1 d . . . . .
H5 H 0.4939 0.7598 0.3248 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3079(3) 0.84117(12) 0.22432(9) 0.0409(3) Uani 1 1 d . . . . .
H6 H 0.4035 0.8055 0.1842 0.049 Uiso 1 1 calc R U . . .
C7 C -0.3480(3) 1.10817(12) 0.28506(9) 0.0431(3) Uani 1 1 d . . . . .
H7A H -0.4485 1.0514 0.3131 0.052 Uiso 1 1 calc R U . . .
H7B H -0.4662 1.1638 0.2557 0.052 Uiso 1 1 calc R U . . .
H7C H -0.2292 1.1484 0.3265 0.052 Uiso 1 1 calc R U . . .
C8 C 0.2717(3) 0.83532(13) 0.45911(8) 0.0421(3) Uani 1 1 d . . . . .
H8A H 0.4303 0.7879 0.4691 0.051 Uiso 1 1 calc R U . . .
H8B H 0.2985 0.9066 0.4924 0.051 Uiso 1 1 calc R U . . .
C9 C 0.0443(3) 0.77015(11) 0.48638(8) 0.0367(3) Uani 1 1 d . . . . .
C10 C -0.0029(3) 0.65217(13) 0.45097(10) 0.0503(4) Uani 1 1 d . . . . .
H10A H 0.0133 0.6549 0.3904 0.060 Uiso 1 1 calc R U . . .
H10B H 0.1336 0.6000 0.4766 0.060 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.3678(16) . ?
O1 H1 0.912(15) . ?
O2 C2 1.3669(15) . ?
O2 C7 1.4293(16) . ?
O9 C9 1.2073(17) . ?
O10 C10 1.4069(19) . ?
O10 H10 0.911(15) . ?
C1 C6 1.3792(19) . ?
C1 C2 1.4001(18) . ?
C2 C3 1.3803(18) . ?
C3 C4 1.3984(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C4 C8 1.5195(18) . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5050(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.497(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 112.3(14) . . ?
C2 O2 C7 116.79(10) . . ?
C10 O10 H10 110.3(13) . . ?
O1 C1 C6 119.56(12) . . ?
O1 C1 C2 120.94(12) . . ?
C6 C1 C2 119.49(12) . . ?
O2 C2 C3 125.45(11) . . ?
O2 C2 C1 114.75(11) . . ?
C3 C2 C1 119.80(12) . . ?
C2 C3 C4 120.71(12) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.97(12) . . ?
C5 C4 C8 122.22(12) . . ?
C3 C4 C8 118.78(12) . . ?
C4 C5 C6 120.52(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.50(13) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C4 110.72(11) . . ?
C9 C8 H8A 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O9 C9 C10 120.25(13) . . ?
O9 C9 C8 122.84(13) . . ?
C10 C9 C8 116.91(12) . . ?
O10 C10 C9 114.23(12) . . ?
O10 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
O10 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O2 C2 C3 -0.46(18) . . . . ?
C7 O2 C2 C1 179.86(11) . . . . ?
O1 C1 C2 O2 -1.18(18) . . . . ?
C6 C1 C2 O2 178.55(11) . . . . ?
O1 C1 C2 C3 179.12(12) . . . . ?
C6 C1 C2 C3 -1.15(19) . . . . ?
O2 C2 C3 C4 -179.19(11) . . . . ?
C1 C2 C3 C4 0.47(19) . . . . ?
C2 C3 C4 C5 0.26(19) . . . . ?
C2 C3 C4 C8 -177.71(12) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C8 C4 C5 C6 177.58(12) . . . . ?
O1 C1 C6 C5 -179.16(12) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C5 C4 C8 C9 -109.62(15) . . . . ?
C3 C4 C8 C9 68.28(16) . . . . ?
C4 C8 C9 O9 -112.84(15) . . . . ?
C4 C8 C9 C10 67.29(16) . . . . ?
O9 C9 C10 O10 13.6(2) . . . . ?
C8 C9 C10 O10 -166.50(12) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1500179'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;
_audit_creation_date             2016-08-19
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C11 H14 O5'
_chemical_formula_moiety         'C11 H14 O5'
_chemical_formula_weight         226.23
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.9885(19)
_cell_length_b                   10.680(3)
_cell_length_c                   12.967(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.113(6)
_cell_angle_gamma                90.0000
_cell_volume                     1106.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1099
_cell_measurement_theta_min      18.30
_cell_measurement_theta_max      46.80
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480.00
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_T_max  0.955

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            11222
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_theta_max         68.030
_diffrn_reflns_theta_min         5.366
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2005
_reflns_number_gt                1834
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1443
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2005
_refine_ls_number_parameters     156
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0865P)²+0.0532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0148(18)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.17789(11) 0.07301(10) 0.66965(7) 0.0374(3) Uani 1 1 d D . . . .
H1 H 0.177(3) 0.0343(19) 0.7330(13) 0.068(6) Uiso 1 1 d D . . . .
O2 O 0.43333(12) -0.00421(9) 0.78853(7) 0.0393(3) Uani 1 1 d . . . . .
O6 O 0.22440(12) 0.18405(10) 0.49197(7) 0.0385(3) Uani 1 1 d . . . . .
O9 O 0.88776(13) 0.36932(10) 0.47905(8) 0.0452(4) Uani 1 1 d . . . . .
O10 O 0.96728(13) 0.45839(10) 0.66709(8) 0.0427(4) Uani 1 1 d D . . . .
H10 H 0.990(3) 0.493(2) 0.6028(14) 0.081(7) Uiso 1 1 d D . . . .
C1 C 0.33902(16) 0.09294(12) 0.63959(10) 0.0300(4) Uani 1 1 d . . . . .
C2 C 0.47585(17) 0.05559(12) 0.69872(10) 0.0308(4) Uani 1 1 d . . . . .
C3 C 0.63863(16) 0.07689(12) 0.66521(10) 0.0330(4) Uani 1 1 d . . . . .
H3 H 0.7312 0.0529 0.7068 0.040 Uiso 1 1 calc R U . . .
C4 C 0.66430(16) 0.13374(12) 0.57014(10) 0.0319(4) Uani 1 1 d . . . . .
C5 C 0.52843(17) 0.17109(12) 0.51034(10) 0.0311(4) Uani 1 1 d . . . . .
H5 H 0.5467 0.2105 0.4456 0.037 Uiso 1 1 calc R U . . .
C6 C 0.36621(17) 0.15105(12) 0.54485(10) 0.0305(4) Uani 1 1 d . . . . .
C7 C 0.5648(2) -0.03768(16) 0.85687(11) 0.0456(4) Uani 1 1 d . . . . .
H7A H 0.6280 0.0374 0.8761 0.055 Uiso 1 1 calc R U . . .
H7B H 0.6396 -0.0974 0.8228 0.055 Uiso 1 1 calc R U . . .
H7C H 0.5176 -0.0762 0.9190 0.055 Uiso 1 1 calc R U . . .
C8 C 0.84012(17) 0.15735(13) 0.53102(11) 0.0352(4) Uani 1 1 d . . . . .
H8A H 0.9199 0.1023 0.5680 0.042 Uiso 1 1 calc R U . . .
H8B H 0.8459 0.1371 0.4566 0.042 Uiso 1 1 calc R U . . .
C9 C 0.88831(15) 0.29233(13) 0.54758(10) 0.0331(4) Uani 1 1 d . . . . .
C10 C 0.93763(19) 0.32917(13) 0.65488(11) 0.0398(4) Uani 1 1 d . . . . .
H10A H 0.8477 0.3036 0.7029 0.048 Uiso 1 1 calc R U . . .
H10B H 1.0403 0.2829 0.6743 0.048 Uiso 1 1 calc R U . . .
C11 C 0.24582(19) 0.24698(15) 0.39651(11) 0.0419(4) Uani 1 1 d . . . . .
H11A H 0.3002 0.3279 0.4085 0.050 Uiso 1 1 calc R U . . .
H11B H 0.1363 0.2605 0.3642 0.050 Uiso 1 1 calc R U . . .
H11C H 0.3158 0.1960 0.3509 0.050 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.3624(16) . ?
O1 H1 0.919(15) . ?
O2 C2 1.3715(16) . ?
O2 C7 1.4186(17) . ?
O6 C6 1.3692(16) . ?
O6 C11 1.4192(17) . ?
O9 C9 1.2107(17) . ?
O10 C10 1.4091(18) . ?
O10 H10 0.932(16) . ?
C1 C2 1.3923(19) . ?
C1 C6 1.3938(19) . ?
C2 C3 1.3906(19) . ?
C3 C4 1.3898(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3911(19) . ?
C4 C8 1.5153(18) . ?
C5 C6 1.3883(19) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5074(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.498(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C1 O1 H1 109.7(13) . . ?
C2 O2 C7 117.61(11) . . ?
C6 O6 C11 117.24(11) . . ?
C10 O10 H10 108.9(15) . . ?
O1 C1 C2 122.60(12) . . ?
O1 C1 C6 118.08(11) . . ?
C2 C1 C6 119.30(12) . . ?
O2 C2 C3 125.09(11) . . ?
O2 C2 C1 113.93(12) . . ?
C3 C2 C1 120.97(12) . . ?
C4 C3 C2 119.24(12) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.22(12) . . ?
C3 C4 C8 120.54(11) . . ?
C5 C4 C8 119.23(12) . . ?
C6 C5 C4 120.26(12) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
O6 C6 C5 124.80(12) . . ?
O6 C6 C1 115.20(12) . . ?
C5 C6 C1 120.00(12) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C4 110.37(11) . . ?
C9 C8 H8A 109.6 . . ?
C4 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C4 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
O9 C9 C10 120.26(13) . . ?
O9 C9 C8 122.98(12) . . ?
C10 C9 C8 116.76(12) . . ?
O10 C10 C9 113.92(12) . . ?
O10 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
O10 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O6 C11 H11A 109.5 . . ?
O6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
C7 O2 C2 C3 5.62(19) . . . . ?
C7 O2 C2 C1 -175.71(12) . . . . ?
O1 C1 C2 O2 0.88(18) . . . . ?
C6 C1 C2 O2 -177.89(11) . . . . ?
O1 C1 C2 C3 179.61(12) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
O2 C2 C3 C4 177.09(11) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
C2 C3 C4 C5 1.30(19) . . . . ?
C2 C3 C4 C8 -179.53(11) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C8 C4 C5 C6 -179.65(11) . . . . ?
C11 O6 C6 C5 -2.2(2) . . . . ?
C11 O6 C6 C1 178.11(12) . . . . ?
C4 C5 C6 O6 -179.92(12) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
O1 C1 C6 O6 0.93(17) . . . . ?
C2 C1 C6 O6 179.76(11) . . . . ?
O1 C1 C6 C5 -178.81(11) . . . . ?
C2 C1 C6 C5 0.02(19) . . . . ?
C3 C4 C8 C9 -100.90(14) . . . . ?
C5 C4 C8 C9 78.29(15) . . . . ?
C4 C8 C9 O9 -102.28(14) . . . . ?
C4 C8 C9 C10 77.47(15) . . . . ?
O9 C9 C10 O10 4.91(19) . . . . ?
C8 C9 C10 O10 -174.84(11) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 . . . 2.6848(14) 0.919(17) 2.21(2) 111.3(16) no
O1 H1 O10 . . 2_646 2.7083(15) 0.919(17) 1.915(19) 143.3(18) no
O10 H10 O9 . . . 2.6922(16) 0.932(19) 2.23(2) 109.5(17) no
O10 H10 O9 . . 3_766 2.8856(16) 0.932(19) 2.06(2) 147.2(19) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
