# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2015

####################################################################### 
# 
# 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_wz5
_database_code_depnum_ccdc_archive 'CCDC 1413564'
_audit_update_record             
;
2015-07-17 deposited with the CCDC.
2015-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 O6, 2(C3 H7 N O)'
_chemical_formula_sum            'C22 H22 N2 O8'
_chemical_formula_weight         442.42

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'
N N 0.0061 0.0033 '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)/c

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

_cell_length_a                   12.8170(11)
_cell_length_b                   7.3554(6)
_cell_length_c                   11.1126(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.490(3)
_cell_angle_gamma                90.00
_cell_volume                     1036.15(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3344
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      28.97

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9942
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2563
_reflns_number_gt                2023
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0476P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2563
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.20305(7) 0.00564(13) 0.46548(9) 0.0325(2) Uani 1 1 d . . .
O2 O 0.25576(7) 0.39650(14) 0.46651(9) 0.0312(2) Uani 1 1 d . . .
O3 O 0.21211(8) 0.33843(15) 0.26745(9) 0.0335(2) Uani 1 1 d . . .
H3O H 0.2846(18) 0.367(3) 0.2640(19) 0.074(7) Uiso 1 1 d . . .
C1 C 0.11175(9) 0.00704(16) 0.48474(11) 0.0208(2) Uani 1 1 d . . .
C2 C 0.04015(9) 0.16122(16) 0.44355(10) 0.0195(2) Uani 1 1 d . . .
C3 C -0.06761(9) 0.15007(16) 0.45425(10) 0.0197(2) Uani 1 1 d . . .
C4 C -0.13634(10) 0.28901(18) 0.40926(11) 0.0239(3) Uani 1 1 d . . .
H4 H -0.2105(12) 0.279(2) 0.4191(14) 0.028(4) Uiso 1 1 d . . .
C5 C -0.09921(10) 0.43839(18) 0.35249(12) 0.0262(3) Uani 1 1 d . . .
H5 H -0.1446(12) 0.535(2) 0.3204(14) 0.032(4) Uiso 1 1 d . . .
C6 C 0.00733(10) 0.45067(18) 0.34228(11) 0.0244(3) Uani 1 1 d . . .
H6 H 0.0346(12) 0.556(2) 0.3052(14) 0.030(4) Uiso 1 1 d . . .
C7 C 0.07778(9) 0.31476(17) 0.38840(11) 0.0207(3) Uani 1 1 d . . .
C8 C 0.19289(9) 0.34919(16) 0.37998(11) 0.0224(3) Uani 1 1 d . . .
O1S O 0.59701(8) 0.91143(16) 0.25584(10) 0.0388(3) Uani 1 1 d . . .
N1S N 0.47443(8) 0.83079(16) 0.37355(10) 0.0276(3) Uani 1 1 d . . .
C1S C 0.57200(11) 0.84106(19) 0.34943(13) 0.0297(3) Uani 1 1 d . . .
H1S H 0.6247(12) 0.784(2) 0.4133(14) 0.030(4) Uiso 1 1 d . . .
C2S C 0.44988(14) 0.7412(2) 0.48315(15) 0.0372(4) Uani 1 1 d . . .
H2SC H 0.4085(14) 0.633(3) 0.4642(16) 0.049(5) Uiso 1 1 d . . .
H2SB H 0.4107(16) 0.829(3) 0.5281(18) 0.062(6) Uiso 1 1 d . . .
H2SA H 0.5159(16) 0.705(3) 0.5343(18) 0.053(5) Uiso 1 1 d . . .
C3S C 0.38567(13) 0.8965(3) 0.28829(16) 0.0463(4) Uani 1 1 d . . .
H3SC H 0.4088(15) 0.945(3) 0.2129(19) 0.056(5) Uiso 1 1 d . . .
H3SB H 0.3449(19) 0.986(3) 0.323(2) 0.078(7) Uiso 1 1 d . . .
H3SA H 0.338(2) 0.789(4) 0.263(3) 0.101(9) Uiso 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
O1 C1 1.2204(14) . ?
O2 C8 1.2108(15) . ?
O3 C8 1.3122(15) . ?
C1 C2 1.4878(16) . ?
C1 C3 1.4928(16) 3_556 ?
C2 C7 1.4040(17) . ?
C2 C3 1.4060(15) . ?
C3 C4 1.3929(17) . ?
C3 C1 1.4928(16) 3_556 ?
C4 C5 1.3858(19) . ?
C5 C6 1.3898(18) . ?
C6 C7 1.3930(17) . ?
C7 C8 1.5134(16) . ?
O1S C1S 1.2453(17) . ?
N1S C1S 1.3192(17) . ?
N1S C3S 1.4516(19) . ?
N1S C2S 1.4593(18) . ?

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
O1 C1 C2 121.09(11) . . ?
O1 C1 C3 120.70(11) . 3_556 ?
C2 C1 C3 118.16(10) . 3_556 ?
C7 C2 C3 119.27(10) . . ?
C7 C2 C1 120.76(10) . . ?
C3 C2 C1 119.90(10) . . ?
C4 C3 C2 120.26(11) . . ?
C4 C3 C1 117.97(10) . 3_556 ?
C2 C3 C1 121.76(10) . 3_556 ?
C5 C4 C3 120.24(11) . . ?
C4 C5 C6 119.75(12) . . ?
C5 C6 C7 120.97(12) . . ?
C6 C7 C2 119.48(11) . . ?
C6 C7 C8 116.24(11) . . ?
C2 C7 C8 124.22(11) . . ?
O2 C8 O3 125.28(11) . . ?
O2 C8 C7 122.65(11) . . ?
O3 C8 C7 111.76(10) . . ?
C1S N1S C3S 121.56(12) . . ?
C1S N1S C2S 121.54(12) . . ?
C3S N1S C2S 116.76(13) . . ?
O1S C1S N1S 124.20(13) . . ?

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
O3 H3O O1S 0.96(2) 1.60(2) 2.5550(13) 174(2) 2_645

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
