# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_z
_database_code_depnum_ccdc_archive 'CCDC 1430247'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 O8'
_chemical_formula_weight         410.36

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4301(6)
_cell_length_b                   9.8683(6)
_cell_length_c                   11.5227(8)
_cell_angle_alpha                81.308(2)
_cell_angle_beta                 68.130(2)
_cell_angle_gamma                68.113(2)
_cell_volume                     923.30(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9475
_exptl_absorpt_correction_T_max  0.9854
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10831
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3228
_reflns_number_gt                2606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0499P)²+0.4995P] 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_number_reflns         3228
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.8533(2) 0.55238(16) 0.15936(15) 0.0417(4) Uani 1 1 d . . .
O2 O 0.84383(16) 0.78215(15) 0.10053(13) 0.0314(4) Uani 1 1 d . . .
O3 O 1.53544(19) 0.68483(19) 0.00350(15) 0.0454(4) Uani 1 1 d . . .
O4 O 1.33044(19) 0.62850(18) 0.15007(14) 0.0418(4) Uani 1 1 d . . .
O5 O 0.97036(17) 1.11042(16) -0.40486(14) 0.0339(4) Uani 1 1 d . . .
O6 O 0.74764(18) 1.04095(16) -0.29066(15) 0.0382(4) Uani 1 1 d . . .
O7 O 1.86539(18) 0.58565(17) -0.56631(14) 0.0387(4) Uani 1 1 d . . .
O8 O 1.67635(17) 0.47006(15) -0.50115(13) 0.0337(4) Uani 1 1 d . . .
C1 C 0.8005(3) 1.1425(2) -0.3828(2) 0.0336(5) Uani 1 1 d . . .
H1A H 0.7366 1.2436 -0.3527 0.040 Uiso 1 1 calc R . .
H1B H 0.7850 1.1329 -0.4611 0.040 Uiso 1 1 calc R . .
C2 C 1.0028(2) 1.0142(2) -0.31005(19) 0.0268(5) Uani 1 1 d . . .
C3 C 1.1431(2) 0.9605(2) -0.28275(19) 0.0265(5) Uani 1 1 d . . .
H3A H 1.2355 0.9865 -0.3325 0.032 Uiso 1 1 calc R . .
C4 C 1.1469(2) 0.8650(2) -0.17819(18) 0.0249(4) Uani 1 1 d . . .
C5 C 1.3038(2) 0.8123(2) -0.14708(19) 0.0264(5) Uani 1 1 d . . .
H5A H 1.3099 0.8980 -0.1152 0.032 Uiso 1 1 calc R . .
C6 C 1.2951(2) 0.6989(2) -0.04275(18) 0.0276(5) Uani 1 1 d . . .
H6A H 1.3203 0.6038 -0.0800 0.033 Uiso 1 1 calc R . .
C7 C 1.4045(3) 0.6727(2) 0.0331(2) 0.0360(5) Uani 1 1 d . . .
C8 C 1.1719(3) 0.6260(3) 0.1607(2) 0.0379(5) Uani 1 1 d . . .
H8A H 1.0903 0.6577 0.2445 0.045 Uiso 1 1 calc R . .
H8B H 1.1796 0.5273 0.1448 0.045 Uiso 1 1 calc R . .
C9 C 1.1294(2) 0.7346(2) 0.05957(19) 0.0288(5) Uani 1 1 d . . .
H9A H 1.0954 0.8358 0.0892 0.035 Uiso 1 1 calc R . .
C10 C 1.0071(2) 0.7287(2) 0.00787(19) 0.0281(5) Uani 1 1 d . . .
H10A H 1.0331 0.6260 -0.0145 0.034 Uiso 1 1 calc R . .
C11 C 1.0100(2) 0.8274(2) -0.10745(18) 0.0255(4) Uani 1 1 d . . .
C12 C 0.8694(2) 0.8808(2) -0.1412(2) 0.0288(5) Uani 1 1 d . . .
H12A H 0.7773 0.8528 -0.0954 0.035 Uiso 1 1 calc R . .
C13 C 0.8696(2) 0.9735(2) -0.24142(19) 0.0276(5) Uani 1 1 d . . .
C14 C 0.7817(3) 0.6818(2) 0.17031(19) 0.0288(5) Uani 1 1 d . . .
C15 C 0.6158(3) 0.7514(3) 0.2597(2) 0.0390(6) Uani 1 1 d . . .
H15A H 0.5741 0.6757 0.3090 0.059 Uiso 1 1 calc R . .
H15B H 0.5439 0.8100 0.2135 0.059 Uiso 1 1 calc R . .
H15C H 0.6196 0.8146 0.3156 0.059 Uiso 1 1 calc R . .
C16 C 1.4558(2) 0.7564(2) -0.26106(19) 0.0262(5) Uani 1 1 d . . .
C17 C 1.5724(3) 0.8235(2) -0.3003(2) 0.0333(5) Uani 1 1 d . . .
H17A H 1.5539 0.9056 -0.2558 0.040 Uiso 1 1 calc R . .
C18 C 1.7157(3) 0.7745(2) -0.4028(2) 0.0369(5) Uani 1 1 d . . .
H18A H 1.7937 0.8222 -0.4300 0.044 Uiso 1 1 calc R . .
C19 C 1.7375(2) 0.6545(2) -0.4618(2) 0.0323(5) Uani 1 1 d . . .
C20 C 1.6234(2) 0.5862(2) -0.42322(19) 0.0273(5) Uani 1 1 d . . .
C21 C 1.4800(2) 0.6356(2) -0.32552(19) 0.0274(5) Uani 1 1 d . . .
H21A H 1.4005 0.5900 -0.3024 0.033 Uiso 1 1 calc R . .
C22 C 1.8460(3) 0.4491(2) -0.5662(2) 0.0359(5) Uani 1 1 d . . .
H22A H 1.9136 0.3732 -0.5232 0.043 Uiso 1 1 calc R . .
H22B H 1.8797 0.4178 -0.6530 0.043 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 C14 1.203(2) . ?
O2 C14 1.346(2) . ?
O2 C10 1.459(2) . ?
O3 C7 1.200(3) . ?
O4 C7 1.358(3) . ?
O4 C8 1.463(3) . ?
O5 C2 1.381(2) . ?
O5 C1 1.440(2) . ?
O6 C13 1.374(2) . ?
O6 C1 1.427(3) . ?
O7 C19 1.386(3) . ?
O7 C22 1.425(3) . ?
O8 C20 1.385(2) . ?
O8 C22 1.439(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.367(3) . ?
C2 C13 1.380(3) . ?
C3 C4 1.416(3) . ?
C3 H3A 0.9500 . ?
C4 C11 1.397(3) . ?
C4 C5 1.534(3) . ?
C5 C6 1.514(3) . ?
C5 C16 1.520(3) . ?
C5 H5A 1.0000 . ?
C6 C9 1.516(3) . ?
C6 C7 1.517(3) . ?
C6 H6A 1.0000 . ?
C8 C9 1.523(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.503(3) . ?
C9 H9A 1.0000 . ?
C10 C11 1.522(3) . ?
C10 H10A 1.0000 . ?
C11 C12 1.410(3) . ?
C12 C13 1.360(3) . ?
C12 H12A 0.9500 . ?
C14 C15 1.480(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.390(3) . ?
C16 C21 1.401(3) . ?
C17 C18 1.397(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.366(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.380(3) . ?
C20 C21 1.369(3) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 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
C14 O2 C10 117.34(15) . . ?
C7 O4 C8 109.86(16) . . ?
C2 O5 C1 105.06(15) . . ?
C13 O6 C1 106.22(15) . . ?
C19 O7 C22 103.50(16) . . ?
C20 O8 C22 103.65(15) . . ?
O6 C1 O5 107.63(16) . . ?
O6 C1 H1A 110.2 . . ?
O5 C1 H1A 110.2 . . ?
O6 C1 H1B 110.2 . . ?
O5 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C3 C2 C13 121.67(19) . . ?
C3 C2 O5 128.11(19) . . ?
C13 C2 O5 110.22(17) . . ?
C2 C3 C4 118.08(19) . . ?
C2 C3 H3A 121.0 . . ?
C4 C3 H3A 121.0 . . ?
C11 C4 C3 119.77(18) . . ?
C11 C4 C5 123.63(18) . . ?
C3 C4 C5 116.57(17) . . ?
C6 C5 C16 111.84(16) . . ?
C6 C5 C4 109.81(16) . . ?
C16 C5 C4 112.60(16) . . ?
C6 C5 H5A 107.4 . . ?
C16 C5 H5A 107.4 . . ?
C4 C5 H5A 107.4 . . ?
C5 C6 C9 113.65(16) . . ?
C5 C6 C7 117.85(18) . . ?
C9 C6 C7 101.09(16) . . ?
C5 C6 H6A 107.9 . . ?
C9 C6 H6A 107.9 . . ?
C7 C6 H6A 107.9 . . ?
O3 C7 O4 121.5(2) . . ?
O3 C7 C6 130.1(2) . . ?
O4 C7 C6 108.39(18) . . ?
O4 C8 C9 102.77(17) . . ?
O4 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
O4 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C10 C9 C6 109.46(16) . . ?
C10 C9 C8 120.08(18) . . ?
C6 C9 C8 100.37(16) . . ?
C10 C9 H9A 108.8 . . ?
C6 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
O2 C10 C9 109.76(16) . . ?
O2 C10 C11 107.72(15) . . ?
C9 C10 C11 109.76(17) . . ?
O2 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
C4 C11 C12 120.53(18) . . ?
C4 C11 C10 121.48(17) . . ?
C12 C11 C10 117.99(17) . . ?
C13 C12 C11 118.00(18) . . ?
C13 C12 H12A 121.0 . . ?
C11 C12 H12A 121.0 . . ?
C12 C13 O6 128.74(19) . . ?
C12 C13 C2 121.88(18) . . ?
O6 C13 C2 109.38(17) . . ?
O1 C14 O2 123.40(19) . . ?
O1 C14 C15 125.1(2) . . ?
O2 C14 C15 111.45(18) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 119.87(19) . . ?
C17 C16 C5 120.10(18) . . ?
C21 C16 C5 120.03(18) . . ?
C16 C17 C18 122.3(2) . . ?
C16 C17 H17A 118.8 . . ?
C18 C17 H17A 118.8 . . ?
C19 C18 C17 116.4(2) . . ?
C19 C18 H18A 121.8 . . ?
C17 C18 H18A 121.8 . . ?
C18 C19 C20 121.9(2) . . ?
C18 C19 O7 128.3(2) . . ?
C20 C19 O7 109.74(19) . . ?
C21 C20 C19 122.43(19) . . ?
C21 C20 O8 128.36(19) . . ?
C19 C20 O8 109.16(18) . . ?
C20 C21 C16 117.05(19) . . ?
C20 C21 H21A 121.5 . . ?
C16 C21 H21A 121.5 . . ?
O7 C22 O8 107.02(16) . . ?
O7 C22 H22A 110.3 . . ?
O8 C22 H22A 110.3 . . ?
O7 C22 H22B 110.3 . . ?
O8 C22 H22B 110.3 . . ?
H22A C22 H22B 108.6 . . ?

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
C13 O6 C1 O5 12.1(2) . . . . ?
C2 O5 C1 O6 -11.6(2) . . . . ?
C1 O5 C2 C3 -173.9(2) . . . . ?
C1 O5 C2 C13 6.9(2) . . . . ?
C13 C2 C3 C4 -2.4(3) . . . . ?
O5 C2 C3 C4 178.49(18) . . . . ?
C2 C3 C4 C11 0.7(3) . . . . ?
C2 C3 C4 C5 -177.41(17) . . . . ?
C11 C4 C5 C6 8.3(3) . . . . ?
C3 C4 C5 C6 -173.73(16) . . . . ?
C11 C4 C5 C16 133.60(19) . . . . ?
C3 C4 C5 C16 -48.4(2) . . . . ?
C16 C5 C6 C9 -166.27(16) . . . . ?
C4 C5 C6 C9 -40.5(2) . . . . ?
C16 C5 C6 C7 75.8(2) . . . . ?
C4 C5 C6 C7 -158.47(17) . . . . ?
C8 O4 C7 O3 179.0(2) . . . . ?
C8 O4 C7 C6 -1.4(2) . . . . ?
C5 C6 C7 O3 -29.6(3) . . . . ?
C9 C6 C7 O3 -154.0(2) . . . . ?
C5 C6 C7 O4 150.85(18) . . . . ?
C9 C6 C7 O4 26.4(2) . . . . ?
C7 O4 C8 C9 -24.1(2) . . . . ?
C5 C6 C9 C10 66.4(2) . . . . ?
C7 C6 C9 C10 -166.30(17) . . . . ?
C5 C6 C9 C8 -166.34(17) . . . . ?
C7 C6 C9 C8 -39.1(2) . . . . ?
O4 C8 C9 C10 158.86(17) . . . . ?
O4 C8 C9 C6 39.0(2) . . . . ?
C14 O2 C10 C9 -98.3(2) . . . . ?
C14 O2 C10 C11 142.21(17) . . . . ?
C6 C9 C10 O2 -172.29(15) . . . . ?
C8 C9 C10 O2 72.5(2) . . . . ?
C6 C9 C10 C11 -54.1(2) . . . . ?
C8 C9 C10 C11 -169.26(17) . . . . ?
C3 C4 C11 C12 1.7(3) . . . . ?
C5 C4 C11 C12 179.61(18) . . . . ?
C3 C4 C11 C10 -178.19(17) . . . . ?
C5 C4 C11 C10 -0.2(3) . . . . ?
O2 C10 C11 C4 142.99(18) . . . . ?
C9 C10 C11 C4 23.5(2) . . . . ?
O2 C10 C11 C12 -36.9(2) . . . . ?
C9 C10 C11 C12 -156.33(17) . . . . ?
C4 C11 C12 C13 -2.3(3) . . . . ?
C10 C11 C12 C13 177.53(18) . . . . ?
C11 C12 C13 O6 -178.86(19) . . . . ?
C11 C12 C13 C2 0.7(3) . . . . ?
C1 O6 C13 C12 171.6(2) . . . . ?
C1 O6 C13 C2 -8.0(2) . . . . ?
C3 C2 C13 C12 1.7(3) . . . . ?
O5 C2 C13 C12 -179.00(18) . . . . ?
C3 C2 C13 O6 -178.67(18) . . . . ?
O5 C2 C13 O6 0.6(2) . . . . ?
C10 O2 C14 O1 -0.4(3) . . . . ?
C10 O2 C14 C15 -179.82(17) . . . . ?
C6 C5 C16 C17 -116.6(2) . . . . ?
C4 C5 C16 C17 119.1(2) . . . . ?
C6 C5 C16 C21 62.3(2) . . . . ?
C4 C5 C16 C21 -61.9(2) . . . . ?
C21 C16 C17 C18 -0.3(3) . . . . ?
C5 C16 C17 C18 178.65(19) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C17 C18 C19 O7 178.4(2) . . . . ?
C22 O7 C19 C18 165.6(2) . . . . ?
C22 O7 C19 C20 -16.5(2) . . . . ?
C18 C19 C20 C21 1.4(3) . . . . ?
O7 C19 C20 C21 -176.71(18) . . . . ?
C18 C19 C20 O8 178.94(19) . . . . ?
O7 C19 C20 O8 0.9(2) . . . . ?
C22 O8 C20 C21 -167.6(2) . . . . ?
C22 O8 C20 C19 15.0(2) . . . . ?
C19 C20 C21 C16 -2.9(3) . . . . ?
O8 C20 C21 C16 -179.95(18) . . . . ?
C17 C16 C21 C20 2.3(3) . . . . ?
C5 C16 C21 C20 -176.63(17) . . . . ?
C19 O7 C22 O8 25.7(2) . . . . ?
C20 O8 C22 O7 -25.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1430248'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N3 O6'
_chemical_formula_weight         393.35

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'
N N 0.0061 0.0033 '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)/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                   8.8536(5)
_cell_length_b                   11.6840(7)
_cell_length_c                   16.8730(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.782(2)
_cell_angle_gamma                90.00
_cell_volume                     1724.97(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19705
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3046
_reflns_number_gt                2336
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0337P)²+0.5656P] 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_number_reflns         3046
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.038
_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 0.98249(14) 0.46899(10) 0.13545(7) 0.0344(3) Uani 1 1 d . . .
O2 O 1.11135(14) 0.62852(10) 0.10070(8) 0.0395(3) Uani 1 1 d . . .
O3 O 0.78856(16) 1.24440(10) 0.06893(8) 0.0427(4) Uani 1 1 d . . .
O4 O 0.75311(15) 1.09874(11) 0.15726(8) 0.0382(3) Uani 1 1 d . . .
O5 O 0.53025(15) 0.60300(11) -0.16963(7) 0.0366(3) Uani 1 1 d . . .
O6 O 0.54786(16) 0.72362(11) -0.26948(7) 0.0412(4) Uani 1 1 d . . .
N1 N 0.86818(18) 0.96956(13) -0.18926(9) 0.0348(4) Uani 1 1 d U . .
N2 N 0.94596(18) 1.05717(13) -0.19138(9) 0.0311(4) Uani 1 1 d U . .
N3 N 1.02684(19) 1.13160(14) -0.19498(10) 0.0411(4) Uani 1 1 d . . .
C1 C 0.6054(2) 0.83972(16) -0.27895(11) 0.0398(5) Uani 1 1 d . . .
H1A H 0.5350 0.8837 -0.3190 0.048 Uiso 1 1 calc R . .
H1B H 0.7080 0.8380 -0.2955 0.048 Uiso 1 1 calc R . .
C2 C 0.6121(2) 0.89033(15) -0.19574(10) 0.0303(4) Uani 1 1 d . . .
H2A H 0.5053 0.9092 -0.1879 0.036 Uiso 1 1 calc R . .
C3 C 0.7106(2) 0.99297(15) -0.17016(11) 0.0300(4) Uani 1 1 d . . .
H3A H 0.6671 1.0620 -0.2005 0.036 Uiso 1 1 calc R . .
C4 C 0.71480(19) 1.01264(14) -0.08104(11) 0.0262(4) Uani 1 1 d . . .
C5 C 0.7478(2) 1.12444(14) -0.05293(11) 0.0316(4) Uani 1 1 d . . .
H5A H 0.7609 1.1851 -0.0887 0.038 Uiso 1 1 calc R . .
C6 C 0.7604(2) 1.14264(14) 0.02763(11) 0.0302(4) Uani 1 1 d . . .
C7 C 0.8165(2) 1.21192(16) 0.15131(13) 0.0427(5) Uani 1 1 d . . .
H7A H 0.7672 1.2668 0.1840 0.051 Uiso 1 1 calc R . .
H7B H 0.9277 1.2112 0.1711 0.051 Uiso 1 1 calc R . .
C8 C 0.7371(2) 1.05629(15) 0.07985(11) 0.0288(4) Uani 1 1 d . . .
C9 C 0.69790(19) 0.94772(14) 0.05388(10) 0.0269(4) Uani 1 1 d . . .
H9A H 0.6779 0.8899 0.0905 0.032 Uiso 1 1 calc R . .
C10 C 0.68812(19) 0.92438(14) -0.02845(10) 0.0241(4) Uani 1 1 d . . .
C11 C 0.64352(19) 0.80244(13) -0.05620(10) 0.0238(4) Uani 1 1 d . . .
H11A H 0.5323 0.7930 -0.0532 0.029 Uiso 1 1 calc R . .
C12 C 0.66371(19) 0.78703(14) -0.14373(10) 0.0254(4) Uani 1 1 d . . .
H12A H 0.7749 0.7746 -0.1455 0.030 Uiso 1 1 calc R . .
C13 C 0.5757(2) 0.69253(15) -0.19127(10) 0.0302(4) Uani 1 1 d . . .
C14 C 0.72879(19) 0.71101(13) -0.00298(9) 0.0220(4) Uani 1 1 d . . .
C15 C 0.88727(19) 0.72099(14) 0.02057(10) 0.0269(4) Uani 1 1 d . . .
H15A H 0.9421 0.7852 0.0053 0.032 Uiso 1 1 calc R . .
C16 C 0.95983(19) 0.63469(14) 0.06637(10) 0.0257(4) Uani 1 1 d . . .
C17 C 0.8827(2) 0.53995(14) 0.08780(10) 0.0253(4) Uani 1 1 d . . .
C18 C 0.7291(2) 0.52806(15) 0.06619(10) 0.0295(4) Uani 1 1 d . . .
H18A H 0.6762 0.4629 0.0814 0.035 Uiso 1 1 calc R . .
C19 C 0.6527(2) 0.61646(14) 0.02046(10) 0.0256(4) Uani 1 1 d . . .
H19A H 0.5451 0.6113 0.0051 0.031 Uiso 1 1 calc R . .
C20 C 1.1307(2) 0.51655(15) 0.13383(11) 0.0334(4) Uani 1 1 d . . .
H20A H 1.1886 0.5201 0.1888 0.040 Uiso 1 1 calc R . .
H20B H 1.1884 0.4682 0.1007 0.040 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 C17 1.377(2) . ?
O1 C20 1.429(2) . ?
O2 C16 1.379(2) . ?
O2 C20 1.423(2) . ?
O3 C6 1.381(2) . ?
O3 C7 1.426(2) . ?
O4 C8 1.384(2) . ?
O4 C7 1.446(2) . ?
O5 C13 1.198(2) . ?
O6 C13 1.355(2) . ?
O6 C1 1.466(2) . ?
N1 N2 1.237(2) . ?
N1 C3 1.504(2) . ?
N2 N3 1.134(2) . ?
C1 C2 1.516(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.507(2) . ?
C2 C12 1.521(2) . ?
C2 H2A 1.0000 . ?
C3 C4 1.516(2) . ?
C3 H3A 1.0000 . ?
C4 C10 1.404(2) . ?
C4 C5 1.405(2) . ?
C5 C6 1.364(3) . ?
C5 H5A 0.9500 . ?
C6 C8 1.376(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.369(2) . ?
C9 C10 1.405(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.533(2) . ?
C11 C14 1.520(2) . ?
C11 C12 1.525(2) . ?
C11 H11A 1.0000 . ?
C12 C13 1.509(2) . ?
C12 H12A 1.0000 . ?
C14 C19 1.383(2) . ?
C14 C15 1.404(2) . ?
C15 C16 1.369(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.377(2) . ?
C17 C18 1.360(2) . ?
C18 C19 1.400(2) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 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
C17 O1 C20 105.29(13) . . ?
C16 O2 C20 105.32(13) . . ?
C6 O3 C7 104.70(14) . . ?
C8 O4 C7 104.32(14) . . ?
C13 O6 C1 109.85(13) . . ?
N2 N1 C3 113.22(14) . . ?
N3 N2 N1 174.14(19) . . ?
O6 C1 C2 103.00(14) . . ?
O6 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
O6 C1 H1B 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
C3 C2 C1 120.99(15) . . ?
C3 C2 C12 110.90(14) . . ?
C1 C2 C12 100.99(14) . . ?
C3 C2 H2A 107.7 . . ?
C1 C2 H2A 107.7 . . ?
C12 C2 H2A 107.7 . . ?
N1 C3 C2 108.00(14) . . ?
N1 C3 C4 110.92(14) . . ?
C2 C3 C4 109.28(14) . . ?
N1 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C10 C4 C5 121.07(16) . . ?
C10 C4 C3 122.32(15) . . ?
C5 C4 C3 116.61(15) . . ?
C6 C5 C4 117.55(16) . . ?
C6 C5 H5A 121.2 . . ?
C4 C5 H5A 121.2 . . ?
C5 C6 C8 121.78(16) . . ?
C5 C6 O3 128.18(16) . . ?
C8 C6 O3 109.96(16) . . ?
O3 C7 O4 107.44(15) . . ?
O3 C7 H7A 110.2 . . ?
O4 C7 H7A 110.2 . . ?
O3 C7 H7B 110.2 . . ?
O4 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C9 C8 C6 122.00(17) . . ?
C9 C8 O4 128.20(16) . . ?
C6 C8 O4 109.74(15) . . ?
C8 C9 C10 118.07(16) . . ?
C8 C9 H9A 121.0 . . ?
C10 C9 H9A 121.0 . . ?
C4 C10 C9 119.43(15) . . ?
C4 C10 C11 123.39(15) . . ?
C9 C10 C11 117.16(14) . . ?
C14 C11 C12 111.59(13) . . ?
C14 C11 C10 113.04(13) . . ?
C12 C11 C10 110.04(13) . . ?
C14 C11 H11A 107.3 . . ?
C12 C11 H11A 107.3 . . ?
C10 C11 H11A 107.3 . . ?
C13 C12 C2 100.88(13) . . ?
C13 C12 C11 118.28(14) . . ?
C2 C12 C11 113.32(14) . . ?
C13 C12 H12A 107.9 . . ?
C2 C12 H12A 107.9 . . ?
C11 C12 H12A 107.9 . . ?
O5 C13 O6 120.76(16) . . ?
O5 C13 C12 130.32(16) . . ?
O6 C13 C12 108.91(14) . . ?
C19 C14 C15 119.68(15) . . ?
C19 C14 C11 120.71(15) . . ?
C15 C14 C11 119.59(14) . . ?
C16 C15 C14 117.47(15) . . ?
C16 C15 H15A 121.3 . . ?
C14 C15 H15A 121.3 . . ?
C15 C16 C17 122.09(16) . . ?
C15 C16 O2 128.16(15) . . ?
C17 C16 O2 109.69(14) . . ?
C18 C17 O1 128.37(15) . . ?
C18 C17 C16 121.80(16) . . ?
O1 C17 C16 109.74(15) . . ?
C17 C18 C19 116.86(16) . . ?
C17 C18 H18A 121.6 . . ?
C19 C18 H18A 121.6 . . ?
C14 C19 C18 122.08(16) . . ?
C14 C19 H19A 119.0 . . ?
C18 C19 H19A 119.0 . . ?
O2 C20 O1 107.99(14) . . ?
O2 C20 H20A 110.1 . . ?
O1 C20 H20A 110.1 . . ?
O2 C20 H20B 110.1 . . ?
O1 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?

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
C3 N1 N2 N3 -179(100) . . . . ?
C13 O6 C1 C2 -22.0(2) . . . . ?
O6 C1 C2 C3 159.99(15) . . . . ?
O6 C1 C2 C12 37.27(18) . . . . ?
N2 N1 C3 C2 161.48(15) . . . . ?
N2 N1 C3 C4 -78.79(18) . . . . ?
C1 C2 C3 N1 -50.2(2) . . . . ?
C12 C2 C3 N1 67.67(18) . . . . ?
C1 C2 C3 C4 -170.96(16) . . . . ?
C12 C2 C3 C4 -53.09(19) . . . . ?
N1 C3 C4 C10 -94.51(18) . . . . ?
C2 C3 C4 C10 24.5(2) . . . . ?
N1 C3 C4 C5 85.16(18) . . . . ?
C2 C3 C4 C5 -155.88(15) . . . . ?
C10 C4 C5 C6 3.2(3) . . . . ?
C3 C4 C5 C6 -176.49(15) . . . . ?
C4 C5 C6 C8 -2.1(3) . . . . ?
C4 C5 C6 O3 -178.45(16) . . . . ?
C7 O3 C6 C5 -170.22(18) . . . . ?
C7 O3 C6 C8 13.04(19) . . . . ?
C6 O3 C7 O4 -19.42(18) . . . . ?
C8 O4 C7 O3 18.54(18) . . . . ?
C5 C6 C8 C9 -0.9(3) . . . . ?
O3 C6 C8 C9 176.07(16) . . . . ?
C5 C6 C8 O4 -178.46(16) . . . . ?
O3 C6 C8 O4 -1.5(2) . . . . ?
C7 O4 C8 C9 172.07(18) . . . . ?
C7 O4 C8 C6 -10.58(19) . . . . ?
C6 C8 C9 C10 2.7(3) . . . . ?
O4 C8 C9 C10 179.78(16) . . . . ?
C5 C4 C10 C9 -1.4(2) . . . . ?
C3 C4 C10 C9 178.24(15) . . . . ?
C5 C4 C10 C11 176.73(15) . . . . ?
C3 C4 C10 C11 -3.6(3) . . . . ?
C8 C9 C10 C4 -1.5(2) . . . . ?
C8 C9 C10 C11 -179.78(15) . . . . ?
C4 C10 C11 C14 136.57(16) . . . . ?
C9 C10 C11 C14 -45.3(2) . . . . ?
C4 C10 C11 C12 11.1(2) . . . . ?
C9 C10 C11 C12 -170.77(14) . . . . ?
C3 C2 C12 C13 -167.67(14) . . . . ?
C1 C2 C12 C13 -38.21(17) . . . . ?
C3 C2 C12 C11 64.87(19) . . . . ?
C1 C2 C12 C11 -165.67(14) . . . . ?
C14 C11 C12 C13 75.50(19) . . . . ?
C10 C11 C12 C13 -158.17(14) . . . . ?
C14 C11 C12 C2 -166.77(14) . . . . ?
C10 C11 C12 C2 -40.44(19) . . . . ?
C1 O6 C13 O5 175.80(17) . . . . ?
C1 O6 C13 C12 -3.1(2) . . . . ?
C2 C12 C13 O5 -152.1(2) . . . . ?
C11 C12 C13 O5 -27.9(3) . . . . ?
C2 C12 C13 O6 26.68(18) . . . . ?
C11 C12 C13 O6 150.81(15) . . . . ?
C12 C11 C14 C19 -99.29(17) . . . . ?
C10 C11 C14 C19 136.04(15) . . . . ?
C12 C11 C14 C15 78.76(18) . . . . ?
C10 C11 C14 C15 -45.9(2) . . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
C11 C14 C15 C16 -177.96(15) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
C14 C15 C16 O2 -175.57(16) . . . . ?
C20 O2 C16 C15 -173.59(18) . . . . ?
C20 O2 C16 C17 9.26(18) . . . . ?
C20 O1 C17 C18 175.84(17) . . . . ?
C20 O1 C17 C16 -7.72(18) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
O2 C16 C17 C18 175.75(15) . . . . ?
C15 C16 C17 O1 -178.32(15) . . . . ?
O2 C16 C17 O1 -0.96(19) . . . . ?
O1 C17 C18 C19 176.53(16) . . . . ?
C16 C17 C18 C19 0.5(2) . . . . ?
C15 C14 C19 C18 -1.2(2) . . . . ?
C11 C14 C19 C18 176.83(15) . . . . ?
C17 C18 C19 C14 0.9(2) . . . . ?
C16 O2 C20 O1 -13.95(18) . . . . ?
C17 O1 C20 O2 13.39(18) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042
