# 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_cu_qylz2b_0m
_database_code_depnum_ccdc_archive 'CCDC 1491784'
_audit_update_record             
;
2016-07-09 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 O8'
_chemical_formula_sum            'C17 H16 O8'
_chemical_formula_weight         348.30
_chemical_absolute_configuration unk

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   6.7105(3)
_cell_length_b                   7.8030(4)
_cell_length_c                   15.2397(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.694(2)
_cell_angle_gamma                90.00
_cell_volume                     778.48(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6047
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      68.82

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7361
_exptl_absorpt_correction_T_max  0.8874
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5682
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         68.81
_reflns_number_total             2079
_reflns_number_gt                2061
_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)+(0.0699P)²+8.0468P] 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   -0.2(8)
_refine_ls_number_reflns         2079
_refine_ls_number_parameters     228
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.1075
_refine_ls_wR_factor_ref         0.2892
_refine_ls_wR_factor_gt          0.2890
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.211
_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
O9' O 0.5006(10) 0.8089(10) 0.1892(5) 0.0270(17) Uani 1 1 d . . .
O4 O 0.5291(10) 0.4260(15) 0.6418(4) 0.040(3) Uani 1 1 d . . .
H4 H 0.5246 0.3867 0.6926 0.060 Uiso 1 1 calc R . .
O1' O -0.0672(11) 0.3946(11) 0.2877(5) 0.0292(18) Uani 1 1 d . . .
O11' O -0.0860(10) 0.2304(10) 0.1127(4) 0.0207(15) Uani 1 1 d . . .
O6' O 0.4460(10) 0.5879(10) 0.0954(4) 0.0189(15) Uani 1 1 d . . .
O8' O 0.0345(10) 0.7526(9) 0.1098(4) 0.0206(15) Uani 1 1 d . . .
H8' H -0.0839 0.7293 0.1159 0.031 Uiso 1 1 calc R . .
O10' O 0.0795(10) 0.0410(9) 0.2117(5) 0.0218(16) Uani 1 1 d . . .
O1 O -0.2422(10) 0.4344(14) 0.4222(5) 0.037(2) Uani 1 1 d . . .
H1 H -0.2365 0.4403 0.3678 0.055 Uiso 1 1 calc R . .
C5 C 0.1610(17) 0.4419(17) 0.6226(7) 0.031(3) Uani 1 1 d . . .
H5 H 0.1734 0.4514 0.6857 0.037 Uiso 1 1 calc R . .
C4 C 0.3368(14) 0.4257(16) 0.5879(7) 0.025(2) Uani 1 1 d . . .
C3 C 0.3196(15) 0.4101(16) 0.4978(7) 0.025(2) Uani 1 1 d . . .
H3 H 0.4394 0.3975 0.4748 0.031 Uiso 1 1 calc R . .
C2 C 0.1225(15) 0.4122(15) 0.4362(7) 0.025(2) Uani 1 1 d . . .
C1' C 0.1075(15) 0.3889(13) 0.3407(7) 0.023(2) Uani 1 1 d . . .
C2' C 0.2878(16) 0.3530(14) 0.3020(6) 0.024(2) Uani 1 1 d . . .
H2'1 H 0.3611 0.2525 0.3332 0.029 Uiso 1 1 calc R . .
H2'2 H 0.3817 0.4523 0.3139 0.029 Uiso 1 1 calc R . .
C3' C 0.2365(14) 0.3176(13) 0.2009(6) 0.0163(19) Uani 1 1 d . . .
C7' C 0.1531(13) 0.4659(14) 0.1344(6) 0.0166(19) Uani 1 1 d . . .
C8' C 0.1810(16) 0.6459(13) 0.1697(7) 0.020(2) Uani 1 1 d . . .
H8'1 H 0.1709 0.6555 0.2340 0.024 Uiso 1 1 calc R . .
C9' C 0.3861(14) 0.6929(13) 0.1553(6) 0.020(2) Uani 1 1 d . . .
C10' C 0.0734(15) 0.1816(13) 0.1797(6) 0.018(2) Uani 1 1 d . . .
C11' C -0.0719(14) 0.4143(14) 0.0936(6) 0.020(2) Uani 1 1 d . . .
H11A H -0.1669 0.4809 0.1217 0.024 Uiso 1 1 calc R . .
H11B H -0.1063 0.4354 0.0279 0.024 Uiso 1 1 calc R . .
C6' C 0.2835(14) 0.4589(14) 0.0636(6) 0.019(2) Uani 1 1 d U . .
H6' H 0.2023 0.4848 0.0018 0.023 Uiso 1 1 calc R . .
C5' C 0.3855(14) 0.2828(14) 0.0693(6) 0.020(2) Uani 1 1 d . . .
H5'1 H 0.5125 0.2863 0.0463 0.024 Uiso 1 1 calc R . .
H5'2 H 0.2922 0.1954 0.0355 0.024 Uiso 1 1 calc R . .
C4' C 0.4312(13) 0.2483(13) 0.1714(6) 0.0157(19) Uani 1 1 d . . .
H4'1 H 0.5552 0.3103 0.2026 0.019 Uiso 1 1 calc R . .
H4'2 H 0.4501 0.1242 0.1843 0.019 Uiso 1 1 calc R . .
C1 C -0.0490(14) 0.4317(15) 0.4745(7) 0.025(2) Uani 1 1 d . . .
C6 C -0.0288(15) 0.4440(17) 0.5663(7) 0.028(3) Uani 1 1 d . . .
H6 H -0.1471 0.4540 0.5907 0.034 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
O9' C9' 1.226(13) . ?
O4 C4 1.369(11) . ?
O4 H4 0.8400 . ?
O1' C1' 1.270(12) . ?
O11' C10' 1.361(12) . ?
O11' C11' 1.471(13) . ?
O6' C9' 1.351(12) . ?
O6' C6' 1.485(11) . ?
O8' C8' 1.449(11) . ?
O8' H8' 0.8400 . ?
O10' C10' 1.197(13) . ?
O1 C1 1.365(12) . ?
O1 H1 0.8400 . ?
C5 C6 1.370(15) . ?
C5 C4 1.401(13) . ?
C5 H5 0.9500 . ?
C4 C3 1.358(15) . ?
C3 C2 1.444(13) . ?
C3 H3 0.9500 . ?
C2 C1 1.408(13) . ?
C2 C1' 1.448(15) . ?
C1' C2' 1.485(14) . ?
C2' C3' 1.528(12) . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C3' C10' 1.508(13) . ?
C3' C7' 1.559(14) . ?
C3' C4' 1.568(12) . ?
C7' C8' 1.500(15) . ?
C7' C6' 1.532(12) . ?
C7' C11' 1.555(12) . ?
C8' C9' 1.486(14) . ?
C8' H8'1 1.0000 . ?
C11' H11A 0.9900 . ?
C11' H11B 0.9900 . ?
C6' C5' 1.529(15) . ?
C6' H6' 1.0000 . ?
C5' C4' 1.543(13) . ?
C5' H5'1 0.9900 . ?
C5' H5'2 0.9900 . ?
C4' H4'1 0.9900 . ?
C4' H4'2 0.9900 . ?
C1 C6 1.379(15) . ?
C6 H6 0.9500 . ?

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 O4 H4 109.5 . . ?
C10' O11' C11' 110.3(7) . . ?
C9' O6' C6' 109.0(7) . . ?
C8' O8' H8' 109.5 . . ?
C1 O1 H1 109.5 . . ?
C6 C5 C4 120.6(10) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C3 C4 O4 117.8(8) . . ?
C3 C4 C5 119.9(10) . . ?
O4 C4 C5 122.3(9) . . ?
C4 C3 C2 121.2(9) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C1 C2 C3 116.6(9) . . ?
C1 C2 C1' 123.2(9) . . ?
C3 C2 C1' 120.2(9) . . ?
O1' C1' C2 119.1(9) . . ?
O1' C1' C2' 118.2(9) . . ?
C2 C1' C2' 122.7(8) . . ?
C1' C2' C3' 114.4(8) . . ?
C1' C2' H2'1 108.7 . . ?
C3' C2' H2'1 108.7 . . ?
C1' C2' H2'2 108.7 . . ?
C3' C2' H2'2 108.7 . . ?
H2'1 C2' H2'2 107.6 . . ?
C10' C3' C2' 109.6(8) . . ?
C10' C3' C7' 104.1(8) . . ?
C2' C3' C7' 119.3(9) . . ?
C10' C3' C4' 107.9(8) . . ?
C2' C3' C4' 109.5(8) . . ?
C7' C3' C4' 105.9(7) . . ?
C8' C7' C6' 103.9(8) . . ?
C8' C7' C11' 114.8(8) . . ?
C6' C7' C11' 111.3(8) . . ?
C8' C7' C3' 117.6(8) . . ?
C6' C7' C3' 104.6(7) . . ?
C11' C7' C3' 104.3(7) . . ?
O8' C8' C9' 106.7(8) . . ?
O8' C8' C7' 107.4(8) . . ?
C9' C8' C7' 103.0(8) . . ?
O8' C8' H8'1 113.0 . . ?
C9' C8' H8'1 113.0 . . ?
C7' C8' H8'1 113.0 . . ?
O9' C9' O6' 118.7(9) . . ?
O9' C9' C8' 129.4(9) . . ?
O6' C9' C8' 111.9(9) . . ?
O10' C10' O11' 120.8(9) . . ?
O10' C10' C3' 126.8(9) . . ?
O11' C10' C3' 112.2(8) . . ?
O11' C11' C7' 105.8(8) . . ?
O11' C11' H11A 110.6 . . ?
C7' C11' H11A 110.6 . . ?
O11' C11' H11B 110.6 . . ?
C7' C11' H11B 110.6 . . ?
H11A C11' H11B 108.7 . . ?
O6' C6' C5' 107.6(7) . . ?
O6' C6' C7' 103.8(7) . . ?
C5' C6' C7' 108.1(8) . . ?
O6' C6' H6' 112.3 . . ?
C5' C6' H6' 112.3 . . ?
C7' C6' H6' 112.3 . . ?
C6' C5' C4' 101.6(8) . . ?
C6' C5' H5'1 111.5 . . ?
C4' C5' H5'1 111.5 . . ?
C6' C5' H5'2 111.5 . . ?
C4' C5' H5'2 111.5 . . ?
H5'1 C5' H5'2 109.3 . . ?
C5' C4' C3' 103.6(7) . . ?
C5' C4' H4'1 111.0 . . ?
C3' C4' H4'1 111.0 . . ?
C5' C4' H4'2 111.0 . . ?
C3' C4' H4'2 111.0 . . ?
H4'1 C4' H4'2 109.0 . . ?
O1 C1 C6 117.4(9) . . ?
O1 C1 C2 121.2(10) . . ?
C6 C1 C2 121.4(9) . . ?
C5 C6 C1 120.3(9) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?

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 C5 C4 C3 -1(2) . . . . ?
C6 C5 C4 O4 178.9(12) . . . . ?
O4 C4 C3 C2 -178.7(12) . . . . ?
C5 C4 C3 C2 0.9(19) . . . . ?
C4 C3 C2 C1 0.2(18) . . . . ?
C4 C3 C2 C1' -177.7(11) . . . . ?
C1 C2 C1' O1' 3.6(17) . . . . ?
C3 C2 C1' O1' -178.7(11) . . . . ?
C1 C2 C1' C2' -174.4(11) . . . . ?
C3 C2 C1' C2' 3.3(16) . . . . ?
O1' C1' C2' C3' -3.0(14) . . . . ?
C2 C1' C2' C3' 175.0(10) . . . . ?
C1' C2' C3' C10' -51.3(12) . . . . ?
C1' C2' C3' C7' 68.4(12) . . . . ?
C1' C2' C3' C4' -169.5(9) . . . . ?
C10' C3' C7' C8' 139.2(8) . . . . ?
C2' C3' C7' C8' 16.7(12) . . . . ?
C4' C3' C7' C8' -107.2(9) . . . . ?
C10' C3' C7' C6' -106.3(8) . . . . ?
C2' C3' C7' C6' 131.2(9) . . . . ?
C4' C3' C7' C6' 7.3(10) . . . . ?
C10' C3' C7' C11' 10.7(9) . . . . ?
C2' C3' C7' C11' -111.8(9) . . . . ?
C4' C3' C7' C11' 124.3(8) . . . . ?
C6' C7' C8' O8' 85.0(9) . . . . ?
C11' C7' C8' O8' -36.8(10) . . . . ?
C3' C7' C8' O8' -160.1(7) . . . . ?
C6' C7' C8' C9' -27.4(9) . . . . ?
C11' C7' C8' C9' -149.2(8) . . . . ?
C3' C7' C8' C9' 87.5(9) . . . . ?
C6' O6' C9' O9' -179.9(8) . . . . ?
C6' O6' C9' C8' 0.1(10) . . . . ?
O8' C8' C9' O9' 84.9(13) . . . . ?
C7' C8' C9' O9' -162.2(10) . . . . ?
O8' C8' C9' O6' -95.0(9) . . . . ?
C7' C8' C9' O6' 17.9(10) . . . . ?
C11' O11' C10' O10' 172.4(8) . . . . ?
C11' O11' C10' C3' -11.7(10) . . . . ?
C2' C3' C10' O10' -55.7(12) . . . . ?
C7' C3' C10' O10' 175.6(9) . . . . ?
C4' C3' C10' O10' 63.5(12) . . . . ?
C2' C3' C10' O11' 128.7(8) . . . . ?
C7' C3' C10' O11' 0.0(10) . . . . ?
C4' C3' C10' O11' -112.1(8) . . . . ?
C10' O11' C11' C7' 18.3(9) . . . . ?
C8' C7' C11' O11' -147.4(8) . . . . ?
C6' C7' C11' O11' 94.9(9) . . . . ?
C3' C7' C11' O11' -17.3(9) . . . . ?
C9' O6' C6' C5' -132.1(8) . . . . ?
C9' O6' C6' C7' -17.7(10) . . . . ?
C8' C7' C6' O6' 27.9(9) . . . . ?
C11' C7' C6' O6' 152.0(8) . . . . ?
C3' C7' C6' O6' -96.0(8) . . . . ?
C8' C7' C6' C5' 142.0(8) . . . . ?
C11' C7' C6' C5' -93.9(9) . . . . ?
C3' C7' C6' C5' 18.1(10) . . . . ?
O6' C6' C5' C4' 75.1(8) . . . . ?
C7' C6' C5' C4' -36.4(9) . . . . ?
C6' C5' C4' C3' 39.7(9) . . . . ?
C10' C3' C4' C5' 81.3(9) . . . . ?
C2' C3' C4' C5' -159.4(8) . . . . ?
C7' C3' C4' C5' -29.6(10) . . . . ?
C3 C2 C1 O1 -179.6(11) . . . . ?
C1' C2 C1 O1 -1.8(17) . . . . ?
C3 C2 C1 C6 -1.5(17) . . . . ?
C1' C2 C1 C6 176.3(11) . . . . ?
C4 C5 C6 C1 -1(2) . . . . ?
O1 C1 C6 C5 179.9(12) . . . . ?
C2 C1 C6 C5 1.7(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O9' 0.84 1.94 2.780(11) 175.8 2_646
O1 H1 O1' 0.84 1.88 2.596(10) 143.0 .

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        68.81
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.147
