# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# 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_in3qau_0m
_database_code_depnum_ccdc_archive 'CCDC 1002755'
_audit_update_record             
;
2014-05-13 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_date             2014-03-28T08:22:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H12 O8, C10 H8 N2'
_chemical_formula_sum            'C26 H20 N2 O8'
_chemical_formula_weight         488.44

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7699(3)
_cell_length_b                   7.0007(5)
_cell_length_c                   17.3241(13)
_cell_angle_alpha                99.217(4)
_cell_angle_beta                 94.411(4)
_cell_angle_gamma                95.138(4)
_cell_volume                     566.28(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             254
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.984

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_number            8814
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.392
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.97
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.97
_reflns_number_total             2469
_reflns_number_gt                1348
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0627P)²+0.0351P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.011(4)
_refine_ls_number_reflns         2469
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2306(3) 0.0229(2) 0.07432(9) 0.0821(6) Uani 1 d . .
O2 O -0.4271(3) 0.2459(2) 0.01680(9) 0.0715(5) Uani 1 d . .
O3 O 0.5655(3) 0.2125(2) 0.27166(8) 0.0585(4) Uani 1 d . .
O4 O 0.6685(3) 0.5208(2) 0.32923(9) 0.0729(5) Uani 1 d . .
N1 N -0.0290(3) 0.1317(3) 0.36859(9) 0.0518(4) Uani 1 d . .
C1 C -0.2486(4) 0.1983(3) 0.06589(11) 0.0542(5) Uani 1 d . .
C2 C -0.0514(4) 0.3518(3) 0.11559(11) 0.0491(5) Uani 1 d . .
C3 C 0.1435(4) 0.3044(3) 0.17139(10) 0.0489(5) Uani 1 d . .
H3A H 0.1495 0.1751 0.1773 0.059 Uiso 1 calc . .
C4 C 0.3283(4) 0.4471(3) 0.21808(10) 0.0465(5) Uani 1 d . .
C5 C 0.3194(4) 0.6394(3) 0.20796(12) 0.0603(6) Uani 1 d . .
H5 H 0.4429 0.7368 0.2391 0.072 Uiso 1 calc . .
C6 C 0.1286(5) 0.6867(3) 0.15192(13) 0.0683(7) Uani 1 d . .
H6 H 0.1254 0.8156 0.1452 0.082 Uiso 1 calc . .
C7 C -0.0570(5) 0.5442(3) 0.10594(12) 0.0599(6) Uani 1 d . .
H7 H -0.186 0.5769 0.0684 0.072 Uiso 1 calc . .
C8 C 0.5379(4) 0.3994(3) 0.27860(11) 0.0501(5) Uani 1 d . .
C9 C 0.3900(3) 0.0281(3) 0.47189(10) 0.0422(5) Uani 1 d . .
C10 C 0.3079(4) 0.2145(3) 0.48047(12) 0.0588(6) Uani 1 d . .
H10 H 0.3911 0.3095 0.5216 0.071 Uiso 1 calc . .
C11 C 0.1021(4) 0.2587(3) 0.42770(12) 0.0605(6) Uani 1 d . .
H11 H 0.0529 0.3855 0.4342 0.073 Uiso 1 calc . .
C12 C 0.0498(4) -0.0460(3) 0.36027(12) 0.0623(6) Uani 1 d . .
H12 H -0.0395 -0.1382 0.319 0.075 Uiso 1 calc . .
C13 C 0.2566(4) -0.1027(3) 0.40917(12) 0.0589(6) Uani 1 d . .
H13 H 0.3061 -0.2293 0.3998 0.071 Uiso 1 calc . .
H1 H -0.380(5) -0.097(3) 0.0293(12) 0.088 Uiso 1 d . .
H3 H 0.716(5) 0.193(3) 0.3133(14) 0.088 Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   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 1.269(2) . ?
O1 H1 1.19(2) . ?
O2 C1 1.261(2) . ?
O3 C8 1.314(2) . ?
O3 H3 1.01(3) . ?
O4 C8 1.209(2) . ?
N1 C12 1.321(3) . ?
N1 C11 1.319(2) . ?
C1 C2 1.476(3) . ?
C2 C7 1.386(3) . ?
C2 C3 1.389(2) . ?
C3 C4 1.380(2) . ?
C3 H3A 0.93 . ?
C4 C5 1.389(3) . ?
C4 C8 1.491(2) . ?
C5 C6 1.379(3) . ?
C5 H5 0.93 . ?
C6 C7 1.375(3) . ?
C6 H6 0.93 . ?
C7 H7 0.93 . ?
C9 C13 1.376(3) . ?
C9 C10 1.385(3) . ?
C9 C9 1.498(3) 2_656 ?
C10 C11 1.379(3) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.377(3) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?

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 116.0(10) . . ?
C8 O3 H3 108.5(13) . . ?
C12 N1 C11 116.48(16) . . ?
O2 C1 O1 122.65(19) . . ?
O2 C1 C2 118.99(18) . . ?
O1 C1 C2 118.37(17) . . ?
C7 C2 C3 119.60(18) . . ?
C7 C2 C1 120.05(17) . . ?
C3 C2 C1 120.35(18) . . ?
C4 C3 C2 120.66(18) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 119.10(17) . . ?
C3 C4 C8 121.50(18) . . ?
C5 C4 C8 119.40(17) . . ?
C6 C5 C4 120.37(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 119.87(18) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
O4 C8 O3 123.44(17) . . ?
O4 C8 C4 123.24(18) . . ?
O3 C8 C4 113.32(16) . . ?
C13 C9 C10 116.20(17) . . ?
C13 C9 C9 122.0(2) . 2_656 ?
C10 C9 C9 121.8(2) . 2_656 ?
C11 C10 C9 119.68(18) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C11 C10 123.84(19) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
N1 C12 C13 123.79(19) . . ?
N1 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C9 C13 C12 119.98(19) . . ?
C9 C13 H13 120 . . ?
C12 C13 H13 120 . . ?

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
O2 C1 C2 C7 -2.4(3) . . . . ?
O1 C1 C2 C7 177.4(2) . . . . ?
O2 C1 C2 C3 178.59(18) . . . . ?
O1 C1 C2 C3 -1.6(3) . . . . ?
C7 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C3 C4 -179.94(17) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 C8 179.66(17) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C8 C4 C5 C6 179.52(18) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C3 C2 C7 C6 -0.4(3) . . . . ?
C1 C2 C7 C6 -179.48(19) . . . . ?
C3 C4 C8 O4 -166.85(19) . . . . ?
C5 C4 C8 O4 13.6(3) . . . . ?
C3 C4 C8 O3 12.8(3) . . . . ?
C5 C4 C8 O3 -166.75(17) . . . . ?
C13 C9 C10 C11 0.3(3) . . . . ?
C9 C9 C10 C11 -179.3(2) 2_656 . . . ?
C12 N1 C11 C10 -1.2(3) . . . . ?
C9 C10 C11 N1 1.1(3) . . . . ?
C11 N1 C12 C13 0.0(3) . . . . ?
C10 C9 C13 C12 -1.4(3) . . . . ?
C9 C9 C13 C12 178.1(2) 2_656 . . . ?
N1 C12 C13 C9 1.3(4) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
