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

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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data_fisnam3

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 O6, C6 H6 N2 O'
_chemical_formula_sum            'C21 H16 N2 O7'
_chemical_formula_weight         408.36

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.204(3)
_cell_length_b                   12.534(3)
_cell_length_c                   18.020(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.77(3)
_cell_angle_gamma                90
_cell_volume                     1807.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    2419
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      25.99

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Kuma KM4-CCD kappa-geometry diffractometer with a Sapphire 2 
CCD camera
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10382
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.020
_diffrn_reflns_theta_max         26.073
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3571
_reflns_number_gt                1757
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0450P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3571
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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_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 0.2744(2) 0.17528(13) 0.22512(10) 0.0430(5) Uani 1 1 d . . . . .
O3 O 0.3460(3) -0.06343(16) 0.12662(15) 0.0842(8) Uani 1 1 d . . . . .
H3 H 0.3187 -0.1250 0.1358 0.126 Uiso 1 1 calc R U . . .
O4 O 0.2441(3) -0.14257(16) 0.24226(14) 0.0869(8) Uani 1 1 d . . . . .
O7 O 0.0852(3) 0.23641(17) 0.44959(12) 0.0648(6) Uani 1 1 d . . . . .
H7 H 0.0883 0.2994 0.4357 0.097 Uiso 1 1 calc R U . . .
O13 O 0.5038(3) 0.44191(15) 0.07745(10) 0.0589(6) Uani 1 1 d . . . . .
H13 H 0.5477 0.4541 0.1227 0.088 Uiso 1 1 calc R U . . .
O14 O 0.5331(3) 0.34567(17) -0.05361(11) 0.0649(6) Uani 1 1 d . . . . .
H14 H 0.5465 0.4091 -0.0404 0.097 Uiso 1 1 calc R U . . .
C2 C 0.3178(3) 0.1105(2) 0.17114(16) 0.0440(7) Uani 1 1 d . . . . .
C3 C 0.3064(4) 0.0048(2) 0.17835(18) 0.0543(8) Uani 1 1 d . . . . .
C4 C 0.2517(4) -0.0435(2) 0.24097(18) 0.0555(8) Uani 1 1 d . . . . .
C5 C 0.1548(4) -0.0083(2) 0.35940(19) 0.0590(9) Uani 1 1 d . . . . .
H5 H 0.1449 -0.0818 0.3677 0.071 Uiso 1 1 calc R U . . .
C6 C 0.1151(4) 0.0621(3) 0.40975(18) 0.0593(8) Uani 1 1 d . . . . .
H6 H 0.0792 0.0373 0.4527 0.071 Uiso 1 1 calc R U . . .
C7 C 0.1276(3) 0.1719(2) 0.39764(17) 0.0484(7) Uani 1 1 d . . . . .
C8 C 0.1801(3) 0.2079(2) 0.33560(16) 0.0434(7) Uani 1 1 d . . . . .
H8 H 0.1878 0.2815 0.3269 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2217(3) 0.1351(2) 0.28583(15) 0.0394(7) Uani 1 1 d . . . . .
C10 C 0.2101(3) 0.0260(2) 0.29564(17) 0.0476(7) Uani 1 1 d . . . . .
C11 C 0.3717(3) 0.1713(2) 0.11181(15) 0.0417(7) Uani 1 1 d . . . . .
C12 C 0.4092(3) 0.2784(2) 0.12288(15) 0.0425(7) Uani 1 1 d . . . . .
H12 H 0.3974 0.3117 0.1681 0.051 Uiso 1 1 calc R U . . .
C13 C 0.4632(3) 0.3366(2) 0.06881(16) 0.0446(7) Uani 1 1 d . . . . .
C14 C 0.4787(3) 0.2889(2) 0.00132(16) 0.0488(8) Uani 1 1 d . . . . .
C15 C 0.4415(4) 0.1838(2) -0.01076(17) 0.0562(8) Uani 1 1 d . . . . .
H15 H 0.4513 0.1515 -0.0566 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3894(3) 0.1245(2) 0.04411(17) 0.0536(8) Uani 1 1 d . . . . .
H16 H 0.3655 0.0516 0.0356 0.064 Uiso 1 1 calc R U . . .
O1A O 0.6775(3) 0.46879(15) 0.21454(11) 0.0630(6) Uani 1 1 d . . . . .
N1A N 1.0504(3) 0.44418(19) 0.40497(14) 0.0540(7) Uani 1 1 d . . . . .
N2A N 0.6793(3) 0.64594(18) 0.21208(14) 0.0583(7) Uani 1 1 d . . . . .
H2A1 H 0.6017 0.6482 0.1705 0.070 Uiso 1 1 calc R U . . .
H2A2 H 0.7216 0.7049 0.2336 0.070 Uiso 1 1 calc R U . . .
C7A C 0.7323(3) 0.5539(2) 0.24226(16) 0.0453(7) Uani 1 1 d . . . . .
C2A C 0.9289(3) 0.4562(2) 0.34229(16) 0.0495(7) Uani 1 1 d . . . . .
H2A H 0.8855 0.3946 0.3153 0.059 Uiso 1 1 calc R U . . .
C3A C 0.8640(3) 0.5531(2) 0.31519(15) 0.0428(7) Uani 1 1 d . . . . .
C4A C 0.9285(4) 0.6436(2) 0.35483(17) 0.0553(8) Uani 1 1 d . . . . .
H4A H 0.8875 0.7116 0.3382 0.066 Uiso 1 1 calc R U . . .
C5A C 1.0543(4) 0.6322(3) 0.41936(17) 0.0582(8) Uani 1 1 d . . . . .
H5A H 1.1007 0.6922 0.4476 0.070 Uiso 1 1 calc R U . . .
C6A C 1.1094(4) 0.5332(3) 0.44100(17) 0.0576(8) Uani 1 1 d . . . . .
H6A H 1.1958 0.5267 0.4848 0.069 Uiso 1 1 calc R U . . .


_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 C9 1.359(3) . ?
O1 C2 1.373(3) . ?
O3 C3 1.356(3) . ?
O3 H3 0.8300 . ?
O4 C4 1.244(3) . ?
O7 C7 1.340(3) . ?
O7 H7 0.8300 . ?
O13 C13 1.362(3) . ?
O13 H13 0.8300 . ?
O14 C14 1.372(3) . ?
O14 H14 0.8300 . ?
C2 C3 1.337(4) . ?
C2 C11 1.459(4) . ?
C3 C4 1.437(4) . ?
C4 C10 1.412(4) . ?
C5 C6 1.356(4) . ?
C5 C10 1.393(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.401(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.361(4) . ?
C8 C9 1.375(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.384(4) . ?
C11 C12 1.382(4) . ?
C11 C16 1.389(4) . ?
C12 C13 1.367(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.386(4) . ?
C14 C15 1.358(4) . ?
C15 C16 1.378(4) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
O1A C7A 1.221(3) . ?
N1A C6A 1.327(4) . ?
N1A C2A 1.340(3) . ?
N2A C7A 1.308(3) . ?
N2A H2A1 0.8700 . ?
N2A H2A2 0.8700 . ?
C7A C3A 1.505(4) . ?
C2A C3A 1.372(4) . ?
C2A H2A 0.9400 . ?
C3A C4A 1.382(4) . ?
C4A C5A 1.381(4) . ?
C4A H4A 0.9400 . ?
C5A C6A 1.348(4) . ?
C5A H5A 0.9400 . ?
C6A H6A 0.9400 . ?

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
C9 O1 C2 122.0(2) . . ?
C3 O3 H3 109.5 . . ?
C7 O7 H7 109.5 . . ?
C13 O13 H13 109.5 . . ?
C14 O14 H14 109.5 . . ?
C3 C2 O1 118.9(3) . . ?
C3 C2 C11 128.9(3) . . ?
O1 C2 C11 112.3(2) . . ?
C2 C3 O3 121.7(3) . . ?
C2 C3 C4 122.3(3) . . ?
O3 C3 C4 116.0(3) . . ?
O4 C4 C10 125.6(3) . . ?
O4 C4 C3 117.4(3) . . ?
C10 C4 C3 117.0(3) . . ?
C6 C5 C10 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C10 C5 H5 119.3 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
O7 C7 C8 123.5(3) . . ?
O7 C7 C6 116.4(3) . . ?
C8 C7 C6 120.1(3) . . ?
C7 C8 C9 119.0(3) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
O1 C9 C8 116.6(2) . . ?
O1 C9 C10 120.8(3) . . ?
C8 C9 C10 122.6(3) . . ?
C9 C10 C5 117.0(3) . . ?
C9 C10 C4 119.1(3) . . ?
C5 C10 C4 123.9(3) . . ?
C12 C11 C16 118.3(3) . . ?
C12 C11 C2 119.7(3) . . ?
C16 C11 C2 122.1(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O13 C13 C12 123.0(3) . . ?
O13 C13 C14 116.8(3) . . ?
C12 C13 C14 120.1(3) . . ?
C15 C14 O14 119.0(3) . . ?
C15 C14 C13 119.9(3) . . ?
O14 C14 C13 121.1(3) . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C6A N1A C2A 116.2(3) . . ?
C7A N2A H2A1 120.0 . . ?
C7A N2A H2A2 120.0 . . ?
H2A1 N2A H2A2 120.0 . . ?
O1A C7A N2A 122.8(3) . . ?
O1A C7A C3A 118.6(2) . . ?
N2A C7A C3A 118.5(3) . . ?
N1A C2A C3A 123.9(3) . . ?
N1A C2A H2A 118.1 . . ?
C3A C2A H2A 118.1 . . ?
C2A C3A C4A 117.9(3) . . ?
C2A C3A C7A 117.6(2) . . ?
C4A C3A C7A 124.4(3) . . ?
C5A C4A C3A 118.7(3) . . ?
C5A C4A H4A 120.7 . . ?
C3A C4A H4A 120.7 . . ?
C6A C5A C4A 118.6(3) . . ?
C6A C5A H5A 120.7 . . ?
C4A C5A H5A 120.7 . . ?
N1A C6A C5A 124.7(3) . . ?
N1A C6A H6A 117.6 . . ?
C5A C6A H6A 117.6 . . ?

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
C9 O1 C2 C3 0.6(3) . . . . ?
C9 O1 C2 C11 -179.5(2) . . . . ?
O1 C2 C3 O3 179.4(2) . . . . ?
C11 C2 C3 O3 -0.5(5) . . . . ?
O1 C2 C3 C4 -0.6(4) . . . . ?
C11 C2 C3 C4 179.5(3) . . . . ?
C2 C3 C4 O4 179.5(3) . . . . ?
O3 C3 C4 O4 -0.5(4) . . . . ?
C2 C3 C4 C10 -0.1(4) . . . . ?
O3 C3 C4 C10 179.9(3) . . . . ?
C10 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 O7 179.6(3) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
O7 C7 C8 C9 179.6(2) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C2 O1 C9 C8 -179.4(2) . . . . ?
C2 O1 C9 C10 0.1(3) . . . . ?
C7 C8 C9 O1 -179.6(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
O1 C9 C10 C5 -180.0(2) . . . . ?
C8 C9 C10 C5 -0.5(4) . . . . ?
O1 C9 C10 C4 -0.8(4) . . . . ?
C8 C9 C10 C4 178.6(2) . . . . ?
C6 C5 C10 C9 -0.3(4) . . . . ?
C6 C5 C10 C4 -179.4(3) . . . . ?
O4 C4 C10 C9 -178.7(3) . . . . ?
C3 C4 C10 C9 0.8(4) . . . . ?
O4 C4 C10 C5 0.3(5) . . . . ?
C3 C4 C10 C5 179.9(3) . . . . ?
C3 C2 C11 C12 -166.0(3) . . . . ?
O1 C2 C11 C12 14.0(3) . . . . ?
C3 C2 C11 C16 13.0(4) . . . . ?
O1 C2 C11 C16 -166.9(2) . . . . ?
C16 C11 C12 C13 -0.4(4) . . . . ?
C2 C11 C12 C13 178.7(2) . . . . ?
C11 C12 C13 O13 -179.1(2) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
O13 C13 C14 C15 179.5(2) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
O13 C13 C14 O14 0.3(4) . . . . ?
C12 C13 C14 O14 -179.8(2) . . . . ?
O14 C14 C15 C16 178.9(3) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C11 1.0(4) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
C2 C11 C16 C15 -179.6(3) . . . . ?
C6A N1A C2A C3A -0.7(4) . . . . ?
N1A C2A C3A C4A 0.3(4) . . . . ?
N1A C2A C3A C7A 177.6(3) . . . . ?
O1A C7A C3A C2A 7.1(4) . . . . ?
N2A C7A C3A C2A -174.2(3) . . . . ?
O1A C7A C3A C4A -175.7(3) . . . . ?
N2A C7A C3A C4A 3.0(4) . . . . ?
C2A C3A C4A C5A 0.0(4) . . . . ?
C7A C3A C4A C5A -177.2(3) . . . . ?
C3A C4A C5A C6A 0.1(4) . . . . ?
C2A N1A C6A C5A 0.8(5) . . . . ?
C4A C5A C6A N1A -0.6(5) . . . . ?

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
O7 H7 N1A 0.83 1.90 2.722(3) 168.7 1_455
O13 H13 O1A 0.83 1.77 2.587(3) 168.5 .
O14 H14 O13 0.83 2.00 2.703(3) 142.7 3_665
N2A H2A2 O4 0.87 1.97 2.805(3) 161.3 2_665
N2A H2A1 O14 0.87 2.15 3.000(3) 164.5 3_665
C15 H15 O3 0.94 2.55 3.359(4) 144.5 3_655
C16 H16 O3 0.94 2.22 2.850(4) 124.0 .
C4A H4A O4 0.94 2.43 3.340(4) 162.0 2_665

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 986280'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FisCaf

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 O6, 2(C8 H10 N4 O2)'
_chemical_formula_sum            'C31 H30 N8 O10'
_chemical_formula_weight         674.63

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.553(2)
_cell_length_b                   14.247(5)
_cell_length_c                   15.149(5)
_cell_angle_alpha                66.25(4)
_cell_angle_beta                 79.39(3)
_cell_angle_gamma                81.05(3)
_cell_volume                     1460.6(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3645
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      29.99

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Kuma KM4-CCD kappa-geometry diffractometer with a Sapphire 2 
CCD camera
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14653
_diffrn_reflns_av_unetI/netI     0.1408
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.908
_diffrn_reflns_theta_max         30.052
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7142
_reflns_number_gt                3262
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0330P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7142
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1610
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_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 0.5495(3) 0.69949(13) 0.69951(13) 0.0218(5) Uani 1 1 d . . . . .
O3 O 0.7297(3) 0.53269(14) 0.57034(14) 0.0296(5) Uani 1 1 d . . . . .
H3 H 0.7128 0.5395 0.5147 0.044 Uiso 1 1 calc R U . . .
O7 O 0.2089(3) 1.02026(14) 0.61962(14) 0.0287(5) Uani 1 1 d . . . . .
H7 H 0.1617 1.0668 0.5731 0.043 Uiso 1 1 calc R U . . .
O13 O 0.9844(3) 0.29009(15) 0.83404(15) 0.0373(6) Uani 1 1 d . . . . .
H13 H 1.0248 0.2536 0.8867 0.056 Uiso 1 1 calc R U . . .
O14 O 0.9176(3) 0.30924(14) 1.00918(14) 0.0303(5) Uani 1 1 d . . . . .
H14 H 0.9005 0.3273 1.0567 0.045 Uiso 1 1 calc R U . . .
C2 C 0.6382(4) 0.6154(2) 0.6800(2) 0.0211(7) Uani 1 1 d . . . . .
C3 C 0.6428(4) 0.6145(2) 0.5904(2) 0.0210(7) Uani 1 1 d . . . . .
C4 C 0.5602(4) 0.6984(2) 0.5124(2) 0.0218(7) Uani 1 1 d . . . . .
O4 O 0.5682(3) 0.69468(14) 0.43102(14) 0.0313(6) Uani 1 1 d . . . . .
C5 C 0.3840(4) 0.8706(2) 0.4695(2) 0.0234(7) Uani 1 1 d . . . . .
H5 H 0.3873 0.8751 0.4049 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2963(4) 0.9499(2) 0.4958(2) 0.0227(7) Uani 1 1 d . . . . .
H6 H 0.2368 1.0080 0.4502 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2959(4) 0.94403(19) 0.5905(2) 0.0200(7) Uani 1 1 d . . . . .
C8 C 0.3800(4) 0.8605(2) 0.6582(2) 0.0228(7) Uani 1 1 d . . . . .
H8 H 0.3791 0.8570 0.7222 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4672(4) 0.7805(2) 0.6300(2) 0.0188(7) Uani 1 1 d . . . . .
C10 C 0.4686(4) 0.7831(2) 0.53766(19) 0.0191(7) Uani 1 1 d . . . . .
C11 C 0.7139(4) 0.5381(2) 0.7649(2) 0.0210(7) Uani 1 1 d . . . . .
C12 C 0.8142(4) 0.4475(2) 0.7620(2) 0.0231(7) Uani 1 1 d . . . . .
H12 H 0.8357 0.4367 0.7029 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8822(4) 0.3741(2) 0.8429(2) 0.0226(7) Uani 1 1 d . . . . .
C14 C 0.8488(4) 0.3867(2) 0.9314(2) 0.0240(7) Uani 1 1 d . . . . .
C15 C 0.7512(4) 0.4758(2) 0.9358(2) 0.0274(8) Uani 1 1 d . . . . .
H15 H 0.7297 0.4859 0.9953 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6843(4) 0.5507(2) 0.8534(2) 0.0232(7) Uani 1 1 d . . . . .
H16 H 0.6174 0.6113 0.8575 0.028 Uiso 1 1 calc R U . . .
O2A O 1.5395(3) -0.04284(14) 0.78806(14) 0.0301(5) Uani 1 1 d . . . . .
O9A O 1.4042(3) -0.21344(15) 1.11824(14) 0.0355(6) Uani 1 1 d . . . . .
N1A N 1.4526(4) -0.13066(17) 0.95162(17) 0.0260(6) Uani 1 1 d . . . . .
N3A N 1.3374(3) 0.04186(17) 0.86878(17) 0.0255(6) Uani 1 1 d . . . . .
N5A N 1.1352(3) 0.11709(18) 0.97273(18) 0.0290(6) Uani 1 1 d . . . . .
N7A N 1.1576(3) -0.02035(18) 1.11573(17) 0.0284(6) Uani 1 1 d . . . . .
C1A C 1.5554(4) -0.2248(2) 0.9446(2) 0.0317(8) Uani 1 1 d . . . . .
H1A1 H 1.6751 -0.2323 0.9642 0.047 Uiso 1 1 calc R U . . .
H1A2 H 1.5692 -0.2198 0.8773 0.047 Uiso 1 1 calc R U . . .
H1A3 H 1.4903 -0.2847 0.9875 0.047 Uiso 1 1 calc R U . . .
C2A C 1.4502(4) -0.0439(2) 0.8645(2) 0.0237(7) Uani 1 1 d . . . . .
C3A C 1.3320(4) 0.1344(2) 0.7779(2) 0.0297(8) Uani 1 1 d . . . . .
H3A1 H 1.4441 0.1677 0.7626 0.045 Uiso 1 1 calc R U . . .
H3A2 H 1.2286 0.1825 0.7862 0.045 Uiso 1 1 calc R U . . .
H3A3 H 1.3196 0.1146 0.7246 0.045 Uiso 1 1 calc R U . . .
C4A C 1.2491(4) 0.0402(2) 0.9575(2) 0.0248(7) Uani 1 1 d . . . . .
C6A C 1.0813(4) 0.0765(2) 1.0698(2) 0.0341(8) Uani 1 1 d . . . . .
H6A H 0.9977 0.1125 1.1029 0.041 Uiso 1 1 calc R U . . .
C7A C 1.1279(5) -0.0843(2) 1.2182(2) 0.0376(9) Uani 1 1 d . . . . .
H7A1 H 1.0218 -0.0547 1.2495 0.056 Uiso 1 1 calc R U . . .
H7A2 H 1.2344 -0.0877 1.2482 0.056 Uiso 1 1 calc R U . . .
H7A3 H 1.1073 -0.1537 1.2265 0.056 Uiso 1 1 calc R U . . .
C8A C 1.2673(4) -0.0443(2) 1.0417(2) 0.0220(7) Uani 1 1 d . . . . .
C9A C 1.3752(4) -0.1368(2) 1.0446(2) 0.0260(8) Uani 1 1 d . . . . .
O2B O 0.0929(3) 1.17651(14) 0.45975(14) 0.0271(5) Uani 1 1 d . . . . .
O9B O -0.1165(3) 1.35971(14) 0.16632(14) 0.0291(5) Uani 1 1 d . . . . .
N1B N -0.0083(3) 1.27034(16) 0.31360(16) 0.0201(6) Uani 1 1 d . . . . .
N3B N -0.0819(3) 1.32622(16) 0.44431(16) 0.0216(6) Uani 1 1 d . . . . .
N5B N -0.2560(3) 1.49342(17) 0.40563(17) 0.0243(6) Uani 1 1 d . . . . .
N7B N -0.2800(3) 1.52170(16) 0.25067(17) 0.0227(6) Uani 1 1 d . . . . .
C1B C 0.0906(4) 1.1911(2) 0.2785(2) 0.0271(7) Uani 1 1 d . . . . .
H1B1 H 0.0314 1.1270 0.3116 0.041 Uiso 1 1 calc R U . . .
H1B2 H 0.2157 1.1786 0.2926 0.041 Uiso 1 1 calc R U . . .
H1B3 H 0.0904 1.2151 0.2082 0.041 Uiso 1 1 calc R U . . .
C2B C 0.0043(4) 1.2534(2) 0.4097(2) 0.0213(7) Uani 1 1 d . . . . .
C3B C -0.0771(4) 1.3118(2) 0.5458(2) 0.0308(8) Uani 1 1 d . . . . .
H3B1 H -0.0013 1.2486 0.5772 0.046 Uiso 1 1 calc R U . . .
H3B2 H -0.2001 1.3066 0.5810 0.046 Uiso 1 1 calc R U . . .
H3B3 H -0.0266 1.3707 0.5466 0.046 Uiso 1 1 calc R U . . .
C4B C -0.1717(4) 1.4130(2) 0.3830(2) 0.0206(7) Uani 1 1 d . . . . .
C6B C -0.3190(4) 1.5573(2) 0.3222(2) 0.0275(8) Uani 1 1 d . . . . .
H6B H -0.3851 1.6219 0.3147 0.033 Uiso 1 1 calc R U . . .
C7B C -0.3185(4) 1.5758(2) 0.1508(2) 0.0308(8) Uani 1 1 d . . . . .
H7B1 H -0.2046 1.5897 0.1067 0.046 Uiso 1 1 calc R U . . .
H7B2 H -0.3909 1.6411 0.1444 0.046 Uiso 1 1 calc R U . . .
H7B3 H -0.3859 1.5332 0.1341 0.046 Uiso 1 1 calc R U . . .
C8B C -0.1838(4) 1.4257(2) 0.2902(2) 0.0209(7) Uani 1 1 d . . . . .
C9B C -0.1055(4) 1.3541(2) 0.2487(2) 0.0205(7) Uani 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 C9 1.366(3) . ?
O1 C2 1.391(3) . ?
O3 C3 1.362(3) . ?
O3 H3 0.8400 . ?
O7 C7 1.365(3) . ?
O7 H7 0.8400 . ?
O13 C13 1.360(3) . ?
O13 H13 0.8400 . ?
O14 C14 1.370(3) . ?
O14 H14 0.8400 . ?
C2 C3 1.357(4) . ?
C2 C11 1.458(4) . ?
C3 C4 1.454(4) . ?
C4 O4 1.245(3) . ?
C4 C10 1.448(4) . ?
C5 C6 1.381(4) . ?
C5 C10 1.409(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(4) . ?
C8 C9 1.403(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(4) . ?
C11 C16 1.396(4) . ?
C11 C12 1.404(4) . ?
C12 C13 1.375(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(4) . ?
C14 C15 1.385(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O2A C2A 1.223(3) . ?
O9A C9A 1.232(3) . ?
N1A C9A 1.395(4) . ?
N1A C2A 1.400(4) . ?
N1A C1A 1.474(4) . ?
N3A C4A 1.379(4) . ?
N3A C2A 1.394(4) . ?
N3A C3A 1.476(3) . ?
N5A C4A 1.353(4) . ?
N5A C6A 1.353(4) . ?
N7A C6A 1.359(4) . ?
N7A C8A 1.392(4) . ?
N7A C7A 1.445(4) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C3A H3A3 0.9800 . ?
C4A C8A 1.368(4) . ?
C6A H6A 0.9500 . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8A C9A 1.428(4) . ?
O2B C2B 1.230(3) . ?
O9B C9B 1.236(3) . ?
N1B C2B 1.395(4) . ?
N1B C9B 1.406(3) . ?
N1B C1B 1.480(3) . ?
N3B C2B 1.371(3) . ?
N3B C4B 1.378(3) . ?
N3B C3B 1.473(3) . ?
N5B C6B 1.346(3) . ?
N5B C4B 1.358(3) . ?
N7B C6B 1.341(4) . ?
N7B C8B 1.396(3) . ?
N7B C7B 1.457(3) . ?
C1B H1B1 0.9800 . ?
C1B H1B2 0.9800 . ?
C1B H1B3 0.9800 . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 0.9800 . ?
C4B C8B 1.362(4) . ?
C6B H6B 0.9500 . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C8B C9B 1.406(4) . ?

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
C9 O1 C2 121.0(2) . . ?
C3 O3 H3 109.5 . . ?
C7 O7 H7 109.5 . . ?
C13 O13 H13 109.5 . . ?
C14 O14 H14 109.5 . . ?
C3 C2 O1 119.1(3) . . ?
C3 C2 C11 129.5(3) . . ?
O1 C2 C11 111.4(2) . . ?
C2 C3 O3 119.7(3) . . ?
C2 C3 C4 123.0(3) . . ?
O3 C3 C4 117.3(2) . . ?
O4 C4 C10 123.9(3) . . ?
O4 C4 C3 121.0(3) . . ?
C10 C4 C3 115.1(3) . . ?
C6 C5 C10 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
O7 C7 C8 117.4(3) . . ?
O7 C7 C6 121.2(2) . . ?
C8 C7 C6 121.5(3) . . ?
C7 C8 C9 118.1(3) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
O1 C9 C10 122.0(3) . . ?
O1 C9 C8 116.0(2) . . ?
C10 C9 C8 122.0(3) . . ?
C9 C10 C5 118.4(3) . . ?
C9 C10 C4 119.8(3) . . ?
C5 C10 C4 121.8(3) . . ?
C16 C11 C12 117.5(3) . . ?
C16 C11 C2 120.7(3) . . ?
C12 C11 C2 121.8(3) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
O13 C13 C12 118.4(3) . . ?
O13 C13 C14 121.1(3) . . ?
C12 C13 C14 120.5(3) . . ?
O14 C14 C15 123.8(3) . . ?
O14 C14 C13 117.1(3) . . ?
C15 C14 C13 119.0(3) . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C9A N1A C2A 127.4(3) . . ?
C9A N1A C1A 116.5(2) . . ?
C2A N1A C1A 116.0(2) . . ?
C4A N3A C2A 119.5(2) . . ?
C4A N3A C3A 122.9(2) . . ?
C2A N3A C3A 117.4(2) . . ?
C4A N5A C6A 102.9(2) . . ?
C6A N7A C8A 104.5(2) . . ?
C6A N7A C7A 127.4(3) . . ?
C8A N7A C7A 128.1(3) . . ?
N1A C1A H1A1 109.5 . . ?
N1A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
N1A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
O2A C2A N3A 121.3(3) . . ?
O2A C2A N1A 122.5(3) . . ?
N3A C2A N1A 116.2(3) . . ?
N3A C3A H3A1 109.5 . . ?
N3A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
N3A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
N5A C4A C8A 112.4(3) . . ?
N5A C4A N3A 126.0(3) . . ?
C8A C4A N3A 121.6(3) . . ?
N5A C6A N7A 113.9(3) . . ?
N5A C6A H6A 123.0 . . ?
N7A C6A H6A 123.0 . . ?
N7A C7A H7A1 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
N7A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C4A C8A N7A 106.3(3) . . ?
C4A C8A C9A 123.1(3) . . ?
N7A C8A C9A 130.5(3) . . ?
O9A C9A N1A 122.1(3) . . ?
O9A C9A C8A 126.2(3) . . ?
N1A C9A C8A 111.6(3) . . ?
C2B N1B C9B 126.3(2) . . ?
C2B N1B C1B 115.6(2) . . ?
C9B N1B C1B 118.0(2) . . ?
C2B N3B C4B 119.2(2) . . ?
C2B N3B C3B 120.2(2) . . ?
C4B N3B C3B 120.6(2) . . ?
C6B N5B C4B 102.6(2) . . ?
C6B N7B C8B 105.5(2) . . ?
C6B N7B C7B 126.8(2) . . ?
C8B N7B C7B 127.5(2) . . ?
N1B C1B H1B1 109.5 . . ?
N1B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
N1B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?
O2B C2B N3B 122.1(3) . . ?
O2B C2B N1B 120.4(3) . . ?
N3B C2B N1B 117.5(2) . . ?
N3B C3B H3B1 109.5 . . ?
N3B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
N3B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
N5B C4B C8B 112.8(2) . . ?
N5B C4B N3B 125.9(3) . . ?
C8B C4B N3B 121.4(3) . . ?
N7B C6B N5B 114.0(3) . . ?
N7B C6B H6B 123.0 . . ?
N5B C6B H6B 123.0 . . ?
N7B C7B H7B1 109.5 . . ?
N7B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N7B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C4B C8B N7B 105.1(2) . . ?
C4B C8B C9B 123.8(3) . . ?
N7B C8B C9B 131.0(3) . . ?
O9B C9B C8B 126.8(3) . . ?
O9B C9B N1B 121.6(3) . . ?
C8B C9B N1B 111.6(3) . . ?

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
C9 O1 C2 C3 0.2(4) . . . . ?
C9 O1 C2 C11 -179.4(2) . . . . ?
O1 C2 C3 O3 179.8(2) . . . . ?
C11 C2 C3 O3 -0.7(5) . . . . ?
O1 C2 C3 C4 0.6(4) . . . . ?
C11 C2 C3 C4 -179.9(3) . . . . ?
C2 C3 C4 O4 179.7(3) . . . . ?
O3 C3 C4 O4 0.5(4) . . . . ?
C2 C3 C4 C10 -1.1(4) . . . . ?
O3 C3 C4 C10 179.6(3) . . . . ?
C10 C5 C6 C7 1.6(4) . . . . ?
C5 C6 C7 O7 -179.2(3) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
O7 C7 C8 C9 178.8(3) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C2 O1 C9 C10 -0.3(4) . . . . ?
C2 O1 C9 C8 179.2(3) . . . . ?
C7 C8 C9 O1 179.7(2) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
O1 C9 C10 C5 -178.6(2) . . . . ?
C8 C9 C10 C5 1.9(4) . . . . ?
O1 C9 C10 C4 -0.3(4) . . . . ?
C8 C9 C10 C4 -179.8(3) . . . . ?
C6 C5 C10 C9 -2.3(4) . . . . ?
C6 C5 C10 C4 179.5(3) . . . . ?
O4 C4 C10 C9 -179.9(3) . . . . ?
C3 C4 C10 C9 1.0(4) . . . . ?
O4 C4 C10 C5 -1.7(5) . . . . ?
C3 C4 C10 C5 179.2(3) . . . . ?
C3 C2 C11 C16 -175.9(3) . . . . ?
O1 C2 C11 C16 3.7(4) . . . . ?
C3 C2 C11 C12 2.3(5) . . . . ?
O1 C2 C11 C12 -178.1(3) . . . . ?
C16 C11 C12 C13 -0.4(4) . . . . ?
C2 C11 C12 C13 -178.7(3) . . . . ?
C11 C12 C13 O13 -177.4(3) . . . . ?
C11 C12 C13 C14 1.6(4) . . . . ?
O13 C13 C14 O14 -2.4(4) . . . . ?
C12 C13 C14 O14 178.6(3) . . . . ?
O13 C13 C14 C15 176.9(3) . . . . ?
C12 C13 C14 C15 -2.0(5) . . . . ?
O14 C14 C15 C16 -179.4(3) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C14 C15 C16 C11 -0.1(5) . . . . ?
C12 C11 C16 C15 -0.3(4) . . . . ?
C2 C11 C16 C15 178.0(3) . . . . ?
C4A N3A C2A O2A -175.3(3) . . . . ?
C3A N3A C2A O2A -0.9(4) . . . . ?
C4A N3A C2A N1A 5.6(4) . . . . ?
C3A N3A C2A N1A -179.9(3) . . . . ?
C9A N1A C2A O2A 171.3(3) . . . . ?
C1A N1A C2A O2A -5.8(4) . . . . ?
C9A N1A C2A N3A -9.6(4) . . . . ?
C1A N1A C2A N3A 173.2(3) . . . . ?
C6A N5A C4A C8A -0.8(3) . . . . ?
C6A N5A C4A N3A 178.1(3) . . . . ?
C2A N3A C4A N5A -179.6(3) . . . . ?
C3A N3A C4A N5A 6.2(5) . . . . ?
C2A N3A C4A C8A -0.9(4) . . . . ?
C3A N3A C4A C8A -175.1(3) . . . . ?
C4A N5A C6A N7A 1.0(4) . . . . ?
C8A N7A C6A N5A -0.9(4) . . . . ?
C7A N7A C6A N5A -179.8(3) . . . . ?
N5A C4A C8A N7A 0.3(3) . . . . ?
N3A C4A C8A N7A -178.6(3) . . . . ?
N5A C4A C8A C9A 177.9(3) . . . . ?
N3A C4A C8A C9A -1.0(5) . . . . ?
C6A N7A C8A C4A 0.4(3) . . . . ?
C7A N7A C8A C4A 179.3(3) . . . . ?
C6A N7A C8A C9A -177.0(3) . . . . ?
C7A N7A C8A C9A 1.9(5) . . . . ?
C2A N1A C9A O9A -170.7(3) . . . . ?
C1A N1A C9A O9A 6.5(4) . . . . ?
C2A N1A C9A C8A 7.6(4) . . . . ?
C1A N1A C9A C8A -175.3(3) . . . . ?
C4A C8A C9A O9A 176.2(3) . . . . ?
N7A C8A C9A O9A -6.8(5) . . . . ?
C4A C8A C9A N1A -2.0(4) . . . . ?
N7A C8A C9A N1A 175.0(3) . . . . ?
C4B N3B C2B O2B 176.9(3) . . . . ?
C3B N3B C2B O2B -2.7(4) . . . . ?
C4B N3B C2B N1B -1.7(4) . . . . ?
C3B N3B C2B N1B 178.7(3) . . . . ?
C9B N1B C2B O2B 179.5(3) . . . . ?
C1B N1B C2B O2B -0.1(4) . . . . ?
C9B N1B C2B N3B -1.9(4) . . . . ?
C1B N1B C2B N3B 178.5(2) . . . . ?
C6B N5B C4B C8B -0.8(3) . . . . ?
C6B N5B C4B N3B 179.2(3) . . . . ?
C2B N3B C4B N5B -176.9(3) . . . . ?
C3B N3B C4B N5B 2.7(4) . . . . ?
C2B N3B C4B C8B 3.1(4) . . . . ?
C3B N3B C4B C8B -177.3(3) . . . . ?
C8B N7B C6B N5B 0.3(3) . . . . ?
C7B N7B C6B N5B -175.5(3) . . . . ?
C4B N5B C6B N7B 0.3(3) . . . . ?
N5B C4B C8B N7B 1.0(3) . . . . ?
N3B C4B C8B N7B -179.0(2) . . . . ?
N5B C4B C8B C9B 179.0(3) . . . . ?
N3B C4B C8B C9B -1.0(5) . . . . ?
C6B N7B C8B C4B -0.8(3) . . . . ?
C7B N7B C8B C4B 175.0(3) . . . . ?
C6B N7B C8B C9B -178.6(3) . . . . ?
C7B N7B C8B C9B -2.8(5) . . . . ?
C4B C8B C9B O9B 177.5(3) . . . . ?
N7B C8B C9B O9B -5.0(5) . . . . ?
C4B C8B C9B N1B -2.2(4) . . . . ?
N7B C8B C9B N1B 175.2(3) . . . . ?
C2B N1B C9B O9B -176.1(3) . . . . ?
C1B N1B C9B O9B 3.5(4) . . . . ?
C2B N1B C9B C8B 3.7(4) . . . . ?
C1B N1B C9B C8B -176.7(3) . . . . ?

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 H3 N5B 0.84 1.97 2.749(3) 152.8 1_645
O7 H7 O2B 0.84 1.89 2.724(3) 171.0 .
O13 H13 N5A 0.84 2.01 2.761(3) 148.8 .
O14 H14 O9B 0.84 1.87 2.710(3) 174.4 1_646
C6 H6 O2B 0.95 2.53 3.229(4) 130.9 .
C8 H8 O2A 0.95 2.57 3.285(4) 131.8 1_465
C12 H12 O3 0.95 2.14 2.813(4) 126.7 .
C3A H3A2 O13 0.98 2.41 3.379(4) 170.5 .
C7A H7A2 O2A 0.98 2.55 3.284(4) 131.8 2_857
C7A H7A1 O7 0.98 2.54 3.481(4) 160.9 2_667
C6B H6B O4 0.95 2.33 2.972(4) 124.3 1_465
C7B H7B2 O9A 0.98 2.33 3.298(4) 170.4 1_374

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 986281'
