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

#######################################################################
#
#                 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_r131208b1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Cl2 N14 O12'
_chemical_formula_weight         667.33

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   12.387(3)
_cell_length_b                   11.618(2)
_cell_length_c                   18.866(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2715.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4425
_cell_measurement_theta_min      2.1591
_cell_measurement_theta_max      27.8744

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω 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            24826
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.92
_reflns_number_total             3254
_reflns_number_gt                2375
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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)+(0.0879P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0103(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3254
_refine_ls_number_parameters     220
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1394
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_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 0.16722(14) 0.15643(18) 0.68466(10) 0.0530(5) Uani 1 1 d . . .
O2 O 0.27324(16) 0.04843(17) 0.74728(11) 0.0529(5) Uani 1 1 d . . .
O3 O 0.49514(16) 0.29610(18) 0.90222(9) 0.0530(5) Uani 1 1 d . . .
O4 O 0.5724(2) 0.4427(2) 0.85546(11) 0.0795(8) Uani 1 1 d . . .
O5 O 0.53015(16) 0.52473(19) 0.61065(10) 0.0562(5) Uani 1 1 d . . .
O6 O 0.38613(19) 0.4699(2) 0.55665(11) 0.0721(7) Uani 1 1 d . . .
N1 N 0.25230(16) 0.1373(2) 0.71549(10) 0.0398(5) Uani 1 1 d . . .
N2 N 0.51243(17) 0.3597(2) 0.85273(10) 0.0438(5) Uani 1 1 d . . .
N3 N 0.44904(17) 0.4665(2) 0.60634(11) 0.0423(5) Uani 1 1 d . . .
N4 N 0.32521(16) 0.17601(18) 0.55890(9) 0.0361(5) Uani 1 1 d . . .
N5 N 0.27813(16) 0.15305(19) 0.49426(10) 0.0366(5) Uani 1 1 d D . .
H5 H 0.2354(18) 0.2037(19) 0.4714(13) 0.043(7) Uiso 1 1 d D . .
N6 N 0.37135(17) -0.0188(2) 0.49095(11) 0.0405(5) Uani 1 1 d D . .
H6A H 0.395(2) -0.006(2) 0.5347(7) 0.053(8) Uiso 1 1 d D . .
H6B H 0.389(2) -0.0855(15) 0.4715(13) 0.058(9) Uiso 1 1 d D . .
N7 N 0.27131(18) 0.0397(2) 0.39512(11) 0.0429(5) Uani 1 1 d D . .
H7A H 0.280(2) -0.0281(13) 0.3733(12) 0.045(8) Uiso 1 1 d D . .
H7B H 0.221(2) 0.085(2) 0.3766(14) 0.069(10) Uiso 1 1 d D . .
C1 C 0.33387(18) 0.2293(2) 0.71710(12) 0.0336(5) Uani 1 1 d . . .
C2 C 0.38628(18) 0.2458(2) 0.78074(12) 0.0357(5) Uani 1 1 d . . .
H2 H 0.3744 0.1975 0.8193 0.043 Uiso 1 1 calc R . .
C3 C 0.45724(17) 0.3374(2) 0.78476(11) 0.0351(5) Uani 1 1 d . . .
C4 C 0.47707(18) 0.4097(2) 0.72856(12) 0.0359(5) Uani 1 1 d . . .
H4 H 0.5251 0.4709 0.7327 0.043 Uiso 1 1 calc R . .
C5 C 0.42342(17) 0.3885(2) 0.66581(11) 0.0339(5) Uani 1 1 d . . .
C6 C 0.35005(17) 0.2982(2) 0.65693(12) 0.0328(5) Uani 1 1 d . . .
C7 C 0.29871(19) 0.2700(2) 0.58783(12) 0.0367(6) Uani 1 1 d . . .
H7 H 0.2492 0.3195 0.5668 0.044 Uiso 1 1 calc R . .
C8 C 0.30721(18) 0.0559(2) 0.46037(12) 0.0341(5) Uani 1 1 d . . .
Cl1 Cl 0.63954(5) 0.22048(6) 0.62554(3) 0.0469(2) 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 N1 1.224(3) . ?
O2 N1 1.222(3) . ?
O3 N2 1.210(3) . ?
O4 N2 1.218(3) . ?
O5 N3 1.214(3) . ?
O6 N3 1.220(3) . ?
N1 C1 1.471(3) . ?
N2 C3 1.476(3) . ?
N3 C5 1.477(3) . ?
N4 C7 1.264(3) . ?
N4 N5 1.378(2) . ?
N5 C8 1.346(3) . ?
N5 H5 0.902(10) . ?
N6 C8 1.311(3) . ?
N6 H6A 0.887(9) . ?
N6 H6B 0.885(9) . ?
N7 C8 1.322(3) . ?
N7 H7A 0.895(9) . ?
N7 H7B 0.892(10) . ?
C1 C2 1.378(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C6 C7 1.487(3) . ?
C7 H7 0.9300 . ?

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
O2 N1 O1 124.7(2) . . ?
O2 N1 C1 117.3(2) . . ?
O1 N1 C1 118.0(2) . . ?
O3 N2 O4 124.0(2) . . ?
O3 N2 C3 118.7(2) . . ?
O4 N2 C3 117.3(2) . . ?
O5 N3 O6 124.2(2) . . ?
O5 N3 C5 118.0(2) . . ?
O6 N3 C5 117.8(2) . . ?
C7 N4 N5 116.1(2) . . ?
C8 N5 N4 118.0(2) . . ?
C8 N5 H5 118.4(18) . . ?
N4 N5 H5 123.1(18) . . ?
C8 N6 H6A 119.9(16) . . ?
C8 N6 H6B 123.1(17) . . ?
H6A N6 H6B 116.8(16) . . ?
C8 N7 H7A 120.9(16) . . ?
C8 N7 H7B 121.0(17) . . ?
H7A N7 H7B 115.4(16) . . ?
C2 C1 C6 123.9(2) . . ?
C2 C1 N1 116.3(2) . . ?
C6 C1 N1 119.72(19) . . ?
C1 C2 C3 117.0(2) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 122.8(2) . . ?
C4 C3 N2 118.7(2) . . ?
C2 C3 N2 118.5(2) . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 123.4(2) . . ?
C4 C5 N3 116.0(2) . . ?
C6 C5 N3 120.6(2) . . ?
C5 C6 C1 115.1(2) . . ?
C5 C6 C7 123.3(2) . . ?
C1 C6 C7 121.5(2) . . ?
N4 C7 C6 117.2(2) . . ?
N4 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
N6 C8 N7 121.3(2) . . ?
N6 C8 N5 120.6(2) . . ?
N7 C8 N5 118.1(2) . . ?

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
C7 N4 N5 C8 177.6(2) . . . . ?
O2 N1 C1 C2 -39.8(3) . . . . ?
O1 N1 C1 C2 137.8(2) . . . . ?
O2 N1 C1 C6 143.6(2) . . . . ?
O1 N1 C1 C6 -38.8(3) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
N1 C1 C2 C3 -175.3(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C2 C3 N2 178.2(2) . . . . ?
O3 N2 C3 C4 -179.9(2) . . . . ?
O4 N2 C3 C4 0.7(3) . . . . ?
O3 N2 C3 C2 1.2(3) . . . . ?
O4 N2 C3 C2 -178.1(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
N2 C3 C4 C5 -179.0(2) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 N3 -178.6(2) . . . . ?
O5 N3 C5 C4 16.4(3) . . . . ?
O6 N3 C5 C4 -162.2(2) . . . . ?
O5 N3 C5 C6 -162.6(2) . . . . ?
O6 N3 C5 C6 18.8(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
N3 C5 C6 C1 179.1(2) . . . . ?
C4 C5 C6 C7 -175.2(2) . . . . ?
N3 C5 C6 C7 3.8(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
N1 C1 C6 C5 175.4(2) . . . . ?
C2 C1 C6 C7 174.4(2) . . . . ?
N1 C1 C6 C7 -9.2(3) . . . . ?
N5 N4 C7 C6 -178.7(2) . . . . ?
C5 C6 C7 N4 112.1(3) . . . . ?
C1 C6 C7 N4 -62.9(3) . . . . ?
N4 N5 C8 N6 5.7(3) . . . . ?
N4 N5 C8 N7 -172.8(2) . . . . ?

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
N7 H7B Cl1 0.892(10) 2.470(15) 3.253(3) 147(2) 4_456
N5 H5 Cl1 0.902(10) 2.351(15) 3.196(2) 156(2) 4_456
N6 H6A O4 0.887(9) 2.193(16) 3.014(3) 154(2) 3_646
N6 H6B Cl1 0.885(9) 2.436(15) 3.215(2) 147(2) 5_656
N7 H7A Cl1 0.895(9) 2.447(14) 3.242(3) 148(2) 5_656
N7 H7A O2 0.895(9) 2.48(2) 3.022(3) 119.5(18) 2_554

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.92
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 996727'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N8 O9'
_chemical_formula_weight         360.22

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           ?
_symmetry_space_group_name_H-M   ?

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                   17.6205(13)
_cell_length_b                   10.4858(7)
_cell_length_c                   15.8252(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.333(3)
_cell_angle_gamma                90.00
_cell_volume                     2723.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      172(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            14753
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4767
_reflns_number_gt                2874
_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)+(0.0434P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4767
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
C1 C 0.28591(17) 0.9159(2) 0.20530(18) 0.0216(7) Uani 1 1 d . . .
C2 C 0.32467(16) 0.8912(2) 0.29836(17) 0.0206(7) Uani 1 1 d . . .
C3 C 0.27218(16) 0.8930(2) 0.34657(17) 0.0188(6) Uani 1 1 d . . .
C4 C 0.18958(16) 0.9158(2) 0.30846(18) 0.0225(7) Uani 1 1 d . . .
H4 H 0.1564 0.9152 0.3443 0.027 Uiso 1 1 calc R . .
C5 C 0.15678(16) 0.9395(2) 0.21643(18) 0.0207(6) Uani 1 1 d . . .
C6 C 0.20355(17) 0.9415(2) 0.16394(18) 0.0227(7) Uani 1 1 d . . .
H6 H 0.1802 0.9600 0.1009 0.027 Uiso 1 1 calc R . .
C7 C 0.41296(16) 0.8712(3) 0.34157(18) 0.0231(7) Uani 1 1 d . . .
H7 H 0.4471 0.8709 0.3069 0.028 Uiso 1 1 calc R . .
C8 C 0.55459(16) 0.8208(3) 0.55878(18) 0.0234(7) Uani 1 1 d . . .
C9 C 0.80946(16) 0.0652(2) 0.20070(18) 0.0207(6) Uani 1 1 d . . .
C10 C 0.84877(17) 0.0941(2) 0.29303(18) 0.0210(7) Uani 1 1 d . . .
C11 C 0.79822(17) 0.0850(2) 0.34362(17) 0.0205(6) Uani 1 1 d . . .
C12 C 0.71672(17) 0.0525(3) 0.30779(19) 0.0255(7) Uani 1 1 d . . .
H12 H 0.6848 0.0484 0.3449 0.031 Uiso 1 1 calc R . .
C13 C 0.68348(17) 0.0262(3) 0.21675(19) 0.0249(7) Uani 1 1 d . . .
C14 C 0.72852(17) 0.0299(2) 0.16188(19) 0.0249(7) Uani 1 1 d . . .
H14 H 0.7048 0.0089 0.0993 0.030 Uiso 1 1 calc R . .
C15 C 0.93528(16) 0.1287(3) 0.33278(18) 0.0224(7) Uani 1 1 d . . .
H15 H 0.9697 0.1187 0.2989 0.027 Uiso 1 1 calc R . .
C16 C 1.07986(17) 0.2255(3) 0.53698(18) 0.0228(7) Uani 1 1 d . . .
N1 N 0.33245(15) 0.9066(2) 0.14428(16) 0.0287(6) Uani 1 1 d . . .
N2 N 0.44230(13) 0.8541(2) 0.42735(14) 0.0231(6) Uani 1 1 d . . .
N3 N 0.52409(13) 0.8375(2) 0.46791(14) 0.0265(6) Uani 1 1 d . . .
H3 H 0.5560 0.8375 0.4362 0.032 Uiso 1 1 calc R . .
N4 N 0.50640(14) 0.8225(2) 0.60527(15) 0.0344(7) Uani 1 1 d . . .
H4A H 0.5269 0.8141 0.6647 0.041 Uiso 1 1 calc R . .
H4B H 0.4535 0.8319 0.5771 0.041 Uiso 1 1 calc R . .
N5 N 0.63381(14) 0.8069(2) 0.59882(15) 0.0323(6) Uani 1 1 d . . .
H5A H 0.6556 0.7984 0.6581 0.039 Uiso 1 1 calc R . .
H5B H 0.6651 0.8060 0.5663 0.039 Uiso 1 1 calc R . .
N6 N 0.30208(13) 0.8642(2) 0.44457(15) 0.0231(5) Uani 1 1 d . . .
N7 N 0.06795(15) 0.9586(2) 0.17395(18) 0.0307(6) Uani 1 1 d . . .
N8 N 0.85324(15) 0.0783(3) 0.13726(16) 0.0279(6) Uani 1 1 d . . .
N9 N 0.96350(13) 0.1723(2) 0.41351(15) 0.0222(5) Uani 1 1 d . . .
N10 N 1.04406(13) 0.2038(2) 0.44700(14) 0.0249(6) Uani 1 1 d . . .
H10 H 1.0720 0.2098 0.4110 0.030 Uiso 1 1 calc R . .
N11 N 1.15844(14) 0.2522(2) 0.56904(15) 0.0315(6) Uani 1 1 d . . .
H11A H 1.1839 0.2654 0.6275 0.038 Uiso 1 1 calc R . .
H11B H 1.1854 0.2568 0.5320 0.038 Uiso 1 1 calc R . .
N12 N 1.03717(15) 0.2176(2) 0.58928(15) 0.0333(7) Uani 1 1 d . . .
H12A H 1.0608 0.2303 0.6481 0.040 Uiso 1 1 calc R . .
H12B H 0.9848 0.1996 0.5657 0.040 Uiso 1 1 calc R . .
N13 N 0.82924(14) 0.1144(2) 0.44182(16) 0.0256(6) Uani 1 1 d . . .
N14 N 0.59525(15) -0.0034(2) 0.1766(2) 0.0357(7) Uani 1 1 d . . .
N15 N 0.16296(14) 0.2235(2) 0.31845(15) 0.0243(6) Uani 1 1 d . . .
N16 N 0.37081(14) 0.2542(2) 0.66567(15) 0.0259(6) Uani 1 1 d . . .
O1 O 0.31704(14) 0.9840(2) 0.08268(14) 0.0424(6) Uani 1 1 d . . .
O2 O 0.38111(13) 0.8182(2) 0.15800(13) 0.0393(6) Uani 1 1 d . . .
O3 O 0.30616(12) 0.75146(19) 0.46524(12) 0.0334(5) Uani 1 1 d . . .
O4 O 0.31800(12) 0.9529(2) 0.49779(13) 0.0327(5) Uani 1 1 d . . .
O5 O 0.04042(13) 0.9849(2) 0.09325(14) 0.0440(6) Uani 1 1 d . . .
O6 O 0.02729(13) 0.9433(2) 0.22184(15) 0.0457(6) Uani 1 1 d . . .
O7 O 0.89918(12) 0.1702(2) 0.14834(12) 0.0326(5) Uani 1 1 d . . .
O8 O 0.83924(13) -0.0002(2) 0.07674(14) 0.0425(6) Uani 1 1 d . . .
O9 O 0.86501(13) 0.0315(2) 0.49536(13) 0.0386(6) Uani 1 1 d . . .
O10 O 0.81481(13) 0.2203(2) 0.46293(13) 0.0363(5) Uani 1 1 d . . .
O11 O 0.56524(14) -0.0142(3) 0.09450(16) 0.0623(8) Uani 1 1 d . . .
O12 O 0.55883(13) -0.0159(2) 0.22867(16) 0.0487(6) Uani 1 1 d . . .
O13 O 0.19676(13) 0.1991(2) 0.40079(13) 0.0382(6) Uani 1 1 d . . .
O14 O 0.20304(12) 0.2499(2) 0.27097(13) 0.0398(6) Uani 1 1 d . . .
O15 O 0.08748(13) 0.2183(3) 0.28225(15) 0.0568(7) Uani 1 1 d . . .
O16 O 0.34231(12) 0.2031(2) 0.58917(13) 0.0381(6) Uani 1 1 d . . .
O17 O 0.44466(12) 0.2814(2) 0.69894(13) 0.0368(6) Uani 1 1 d . . .
O18 O 0.32523(12) 0.2772(2) 0.70818(12) 0.0392(6) 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
C1 C6 1.384(4) . ?
C1 C2 1.404(4) . ?
C1 N1 1.480(3) . ?
C2 C3 1.397(4) . ?
C2 C7 1.469(4) . ?
C3 C4 1.379(4) . ?
C3 N6 1.476(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(4) . ?
C5 N7 1.475(4) . ?
C6 H6 0.9500 . ?
C7 N2 1.277(3) . ?
C7 H7 0.9500 . ?
C8 N4 1.310(3) . ?
C8 N5 1.314(3) . ?
C8 N3 1.351(3) . ?
C9 C14 1.382(4) . ?
C9 C10 1.404(4) . ?
C9 N8 1.478(3) . ?
C10 C11 1.401(4) . ?
C10 C15 1.467(4) . ?
C11 C12 1.381(4) . ?
C11 N13 1.480(3) . ?
C12 C13 1.371(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(4) . ?
C13 N14 1.483(4) . ?
C14 H14 0.9500 . ?
C15 N9 1.275(3) . ?
C15 H15 0.9500 . ?
C16 N12 1.308(3) . ?
C16 N11 1.320(3) . ?
C16 N10 1.351(3) . ?
N1 O1 1.220(3) . ?
N1 O2 1.227(3) . ?
N2 N3 1.359(3) . ?
N3 H3 0.8800 . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N6 O4 1.217(3) . ?
N6 O3 1.222(3) . ?
N7 O5 1.221(3) . ?
N7 O6 1.228(3) . ?
N8 O8 1.218(3) . ?
N8 O7 1.229(3) . ?
N9 N10 1.363(3) . ?
N10 H10 0.8800 . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N13 O10 1.213(3) . ?
N13 O9 1.217(3) . ?
N14 O11 1.217(3) . ?
N14 O12 1.221(3) . ?
N15 O14 1.235(3) . ?
N15 O15 1.243(3) . ?
N15 O13 1.247(3) . ?
N16 O18 1.244(3) . ?
N16 O17 1.246(3) . ?
N16 O16 1.250(3) . ?

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
C6 C1 C2 123.9(3) . . ?
C6 C1 N1 116.0(2) . . ?
C2 C1 N1 119.9(3) . . ?
C3 C2 C1 113.9(2) . . ?
C3 C2 C7 123.2(2) . . ?
C1 C2 C7 122.9(2) . . ?
C4 C3 C2 124.5(3) . . ?
C4 C3 N6 114.3(2) . . ?
C2 C3 N6 121.1(2) . . ?
C3 C4 C5 117.6(3) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 N7 119.7(3) . . ?
C4 C5 N7 118.2(3) . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
N2 C7 C2 117.7(2) . . ?
N2 C7 H7 121.1 . . ?
C2 C7 H7 121.1 . . ?
N4 C8 N5 121.5(3) . . ?
N4 C8 N3 120.5(3) . . ?
N5 C8 N3 118.0(3) . . ?
C14 C9 C10 124.0(3) . . ?
C14 C9 N8 115.6(2) . . ?
C10 C9 N8 120.3(2) . . ?
C11 C10 C9 113.9(3) . . ?
C11 C10 C15 123.3(3) . . ?
C9 C10 C15 122.8(2) . . ?
C12 C11 C10 124.4(3) . . ?
C12 C11 N13 114.5(2) . . ?
C10 C11 N13 121.1(2) . . ?
C13 C12 C11 117.6(3) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C12 C13 C14 122.3(3) . . ?
C12 C13 N14 118.2(3) . . ?
C14 C13 N14 119.5(3) . . ?
C13 C14 C9 117.8(3) . . ?
C13 C14 H14 121.1 . . ?
C9 C14 H14 121.1 . . ?
N9 C15 C10 118.9(3) . . ?
N9 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
N12 C16 N11 122.3(3) . . ?
N12 C16 N10 120.1(3) . . ?
N11 C16 N10 117.6(3) . . ?
O1 N1 O2 125.6(3) . . ?
O1 N1 C1 117.5(3) . . ?
O2 N1 C1 116.8(2) . . ?
C7 N2 N3 118.0(2) . . ?
C8 N3 N2 117.5(2) . . ?
C8 N3 H3 121.2 . . ?
N2 N3 H3 121.2 . . ?
C8 N4 H4A 120.0 . . ?
C8 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O4 N6 O3 125.3(2) . . ?
O4 N6 C3 118.4(2) . . ?
O3 N6 C3 116.3(2) . . ?
O5 N7 O6 125.2(3) . . ?
O5 N7 C5 117.3(3) . . ?
O6 N7 C5 117.5(3) . . ?
O8 N8 O7 125.2(2) . . ?
O8 N8 C9 117.7(3) . . ?
O7 N8 C9 117.1(2) . . ?
C15 N9 N10 116.6(2) . . ?
C16 N10 N9 118.1(2) . . ?
C16 N10 H10 120.9 . . ?
N9 N10 H10 120.9 . . ?
C16 N11 H11A 120.0 . . ?
C16 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C16 N12 H12A 120.0 . . ?
C16 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
O10 N13 O9 124.7(2) . . ?
O10 N13 C11 116.5(2) . . ?
O9 N13 C11 118.8(2) . . ?
O11 N14 O12 125.4(3) . . ?
O11 N14 C13 117.2(3) . . ?
O12 N14 C13 117.4(3) . . ?
O14 N15 O15 118.8(2) . . ?
O14 N15 O13 121.4(2) . . ?
O15 N15 O13 119.8(2) . . ?
O18 N16 O17 120.5(2) . . ?
O18 N16 O16 119.7(2) . . ?
O17 N16 O16 119.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 996728'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H8 N10 O10'
_chemical_formula_sum            'C15 H8 N10 O10'
_chemical_formula_weight         488.31

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      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

_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+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'-x, -y, z'
'x, y+1/2, z+1/2'
'-x+1/2, y+1, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x, -y+1/2, z+1/2'

_cell_length_a                   24.962(3)
_cell_length_b                   16.401(2)
_cell_length_c                   9.4116(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3853.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3207
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      29.08

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_F_000             1984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            20323
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.632
_diffrn_reflns_theta_max         29.095
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5023
_reflns_number_gt                2912
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    0.990

_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0064(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 824 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.0(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5023
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1815
_refine_ls_wR_factor_gt          0.1507
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.962
_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 0.36370(18) 0.4587(3) 0.5650(4) 0.0622(12) Uani 1 1 d . . . . .
O2 O 0.31269(18) 0.5646(3) 0.5683(5) 0.0683(13) Uani 1 1 d . . . . .
O3 O 0.29562(17) 0.6424(3) 1.2077(5) 0.0661(12) Uani 1 1 d . . . . .
O4 O 0.26759(18) 0.6944(3) 1.0120(5) 0.0671(12) Uani 1 1 d . . . . .
O5 O 0.54892(16) 0.1689(3) 0.9895(4) 0.0584(11) Uani 1 1 d . . . . .
O6 O 0.61582(19) 0.2335(3) 1.0830(5) 0.0703(13) Uani 1 1 d . . . . .
O7 O 0.7488(4) 0.0930(7) 0.7279(7) 0.207(6) Uani 1 1 d . . . . .
O8 O 0.7372(2) 0.1191(4) 0.5116(6) 0.0851(16) Uani 1 1 d . . . . .
O9 O 0.5860(2) 0.2880(4) 0.3696(5) 0.0856(17) Uani 1 1 d . . . . .
O10 O 0.56832(19) 0.3844(3) 0.5178(5) 0.0676(13) Uani 1 1 d . . . . .
N1 N 0.4209(2) 0.4709(3) 1.2219(5) 0.0499(12) Uani 1 1 d . . . . .
N2 N 0.43093(16) 0.4477(3) 1.0828(5) 0.0418(10) Uani 1 1 d . . . . .
N3 N 0.34172(19) 0.5146(3) 0.6271(5) 0.0510(12) Uani 1 1 d . . . . .
N4 N 0.29416(18) 0.6443(3) 1.0784(6) 0.0511(12) Uani 1 1 d . . . . .
N5 N 0.5028(2) 0.3706(4) 1.1689(6) 0.0527(13) Uani 1 1 d . . . . .
N6 N 0.48520(17) 0.3839(3) 0.9211(5) 0.0461(11) Uani 1 1 d . . . . .
N7 N 0.53226(17) 0.3379(3) 0.9053(5) 0.0442(10) Uani 1 1 d . . . . .
N8 N 0.59113(18) 0.2065(3) 0.9824(5) 0.0463(11) Uani 1 1 d . . . . .
N9 N 0.7266(2) 0.1282(4) 0.6351(6) 0.0714(17) Uani 1 1 d . . . . .
N10 N 0.58616(19) 0.3169(4) 0.4901(5) 0.0541(12) Uani 1 1 d . . . . .
C1 C 0.3816(2) 0.5236(4) 1.2152(6) 0.0472(13) Uani 1 1 d . . . . .
H1 H 0.3665 0.5501 1.2956 0.057 Uiso 1 1 calc R U . . .
C2 C 0.3638(2) 0.5366(3) 1.0715(6) 0.0404(11) Uani 1 1 d . . . . .
C3 C 0.39642(18) 0.4849(3) 0.9877(6) 0.0379(11) Uani 1 1 d . . . . .
C4 C 0.3903(2) 0.4757(3) 0.8420(6) 0.0435(12) Uani 1 1 d . . . . .
H4 H 0.4119 0.4395 0.7878 0.052 Uiso 1 1 calc R U . . .
C5 C 0.3507(2) 0.5225(4) 0.7817(6) 0.0431(12) Uani 1 1 d . . . . .
C6 C 0.3190(2) 0.5791(3) 0.8555(6) 0.0438(12) Uani 1 1 d . . . . .
H6 H 0.2937 0.6123 0.8073 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3261(2) 0.5847(3) 1.0000(6) 0.0435(12) Uani 1 1 d . . . . .
C8 C 0.47633(19) 0.3981(3) 1.0551(6) 0.0407(12) Uani 1 1 d . . . . .
C9 C 0.5392(2) 0.3156(3) 0.7762(6) 0.0446(13) Uani 1 1 d . . . . .
H9 H 0.5138 0.3297 0.7051 0.054 Uiso 1 1 calc R U . . .
C10 C 0.5870(2) 0.2680(3) 0.7403(5) 0.0406(12) Uani 1 1 d . . . . .
C11 C 0.61423(19) 0.2188(3) 0.8385(5) 0.0389(11) Uani 1 1 d . . . . .
C12 C 0.6599(2) 0.1752(4) 0.8104(6) 0.0485(14) Uani 1 1 d . . . . .
H12 H 0.6777 0.1452 0.8826 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6788(2) 0.1769(4) 0.6719(6) 0.0497(14) Uani 1 1 d . . . . .
C14 C 0.6544(2) 0.2215(3) 0.5662(6) 0.0464(12) Uani 1 1 d . . . . .
H14 H 0.6677 0.2211 0.4716 0.056 Uiso 1 1 calc R U . . .
C15 C 0.6098(2) 0.2668(3) 0.6031(5) 0.0407(12) Uani 1 1 d . . . . .
H5A H 0.529(3) 0.340(5) 1.160(8) 0.08(2) Uiso 1 1 d . . . . .
H5B H 0.493(3) 0.390(4) 1.256(9) 0.07(2) 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 N3 1.218(6) . ?
O2 N3 1.226(6) . ?
O3 N4 1.218(7) . ?
O4 N4 1.227(6) . ?
O5 N8 1.223(6) . ?
O6 N8 1.213(6) . ?
O7 N9 1.185(8) . ?
O8 N9 1.202(7) . ?
O9 N10 1.228(7) . ?
O10 N10 1.223(7) . ?
N1 C1 1.311(7) . ?
N1 N2 1.386(6) . ?
N2 C3 1.384(7) . ?
N2 C8 1.419(7) . ?
N3 C5 1.478(7) . ?
N4 C7 1.461(7) . ?
N5 C8 1.337(7) . ?
N5 H5A 0.84(8) . ?
N5 H5B 0.91(8) . ?
N6 C8 1.302(7) . ?
N6 N7 1.404(6) . ?
N7 C9 1.281(7) . ?
N8 C11 1.485(7) . ?
N9 C13 1.476(8) . ?
N10 C15 1.467(7) . ?
C1 C2 1.439(8) . ?
C1 H1 0.9500 . ?
C2 C7 1.401(7) . ?
C2 C3 1.415(7) . ?
C3 C4 1.388(7) . ?
C4 C5 1.374(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(8) . ?
C6 C7 1.374(7) . ?
C6 H6 0.9500 . ?
C9 C10 1.466(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(7) . ?
C10 C15 1.411(7) . ?
C11 C12 1.371(7) . ?
C12 C13 1.387(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(8) . ?
C14 C15 1.383(7) . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 105.7(5) . . ?
C3 N2 N1 112.2(4) . . ?
C3 N2 C8 129.2(4) . . ?
N1 N2 C8 118.3(4) . . ?
O1 N3 O2 123.6(5) . . ?
O1 N3 C5 118.0(5) . . ?
O2 N3 C5 118.4(5) . . ?
O3 N4 O4 122.8(5) . . ?
O3 N4 C7 118.2(5) . . ?
O4 N4 C7 119.0(5) . . ?
C8 N5 H5A 121(5) . . ?
C8 N5 H5B 118(5) . . ?
H5A N5 H5B 121(7) . . ?
C8 N6 N7 109.9(4) . . ?
C9 N7 N6 111.5(4) . . ?
O6 N8 O5 125.4(5) . . ?
O6 N8 C11 117.7(5) . . ?
O5 N8 C11 116.9(4) . . ?
O7 N9 O8 123.3(6) . . ?
O7 N9 C13 118.0(6) . . ?
O8 N9 C13 118.2(6) . . ?
O10 N10 O9 123.0(5) . . ?
O10 N10 C15 119.9(5) . . ?
O9 N10 C15 117.0(5) . . ?
N1 C1 C2 111.9(5) . . ?
N1 C1 H1 124.0 . . ?
C2 C1 H1 124.0 . . ?
C7 C2 C3 117.2(5) . . ?
C7 C2 C1 137.9(5) . . ?
C3 C2 C1 104.9(5) . . ?
N2 C3 C4 131.3(5) . . ?
N2 C3 C2 105.2(4) . . ?
C4 C3 C2 123.5(5) . . ?
C5 C4 C3 115.2(5) . . ?
C5 C4 H4 122.4 . . ?
C3 C4 H4 122.4 . . ?
C4 C5 C6 124.8(5) . . ?
C4 C5 N3 117.8(5) . . ?
C6 C5 N3 117.4(5) . . ?
C7 C6 C5 117.5(5) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C2 121.6(5) . . ?
C6 C7 N4 118.4(5) . . ?
C2 C7 N4 120.0(5) . . ?
N6 C8 N5 129.2(5) . . ?
N6 C8 N2 114.6(5) . . ?
N5 C8 N2 116.2(5) . . ?
N7 C9 C10 118.8(5) . . ?
N7 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C15 113.6(5) . . ?
C11 C10 C9 123.2(5) . . ?
C15 C10 C9 123.2(5) . . ?
C12 C11 C10 125.1(5) . . ?
C12 C11 N8 115.3(5) . . ?
C10 C11 N8 119.4(4) . . ?
C11 C12 C13 117.1(5) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 H12 121.5 . . ?
C14 C13 C12 122.5(5) . . ?
C14 C13 N9 118.4(5) . . ?
C12 C13 N9 119.1(5) . . ?
C13 C14 C15 117.4(5) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C10 124.2(5) . . ?
C14 C15 N10 116.3(5) . . ?
C10 C15 N10 119.5(5) . . ?

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
C1 N1 N2 C3 -1.5(6) . . . . ?
C1 N1 N2 C8 172.3(5) . . . . ?
C8 N6 N7 C9 173.2(5) . . . . ?
N2 N1 C1 C2 0.5(6) . . . . ?
N1 C1 C2 C7 -178.1(6) . . . . ?
N1 C1 C2 C3 0.6(6) . . . . ?
N1 N2 C3 C4 -175.7(6) . . . . ?
C8 N2 C3 C4 11.3(9) . . . . ?
N1 N2 C3 C2 1.9(6) . . . . ?
C8 N2 C3 C2 -171.1(5) . . . . ?
C7 C2 C3 N2 177.6(4) . . . . ?
C1 C2 C3 N2 -1.5(5) . . . . ?
C7 C2 C3 C4 -4.5(8) . . . . ?
C1 C2 C3 C4 176.4(5) . . . . ?
N2 C3 C4 C5 179.0(5) . . . . ?
C2 C3 C4 C5 1.8(8) . . . . ?
C3 C4 C5 C6 2.6(8) . . . . ?
C3 C4 C5 N3 -179.2(5) . . . . ?
O1 N3 C5 C4 11.2(8) . . . . ?
O2 N3 C5 C4 -168.8(5) . . . . ?
O1 N3 C5 C6 -170.6(5) . . . . ?
O2 N3 C5 C6 9.5(8) . . . . ?
C4 C5 C6 C7 -3.9(9) . . . . ?
N3 C5 C6 C7 177.9(5) . . . . ?
C5 C6 C7 C2 0.8(8) . . . . ?
C5 C6 C7 N4 178.9(5) . . . . ?
C3 C2 C7 C6 3.1(7) . . . . ?
C1 C2 C7 C6 -178.2(6) . . . . ?
C3 C2 C7 N4 -175.0(5) . . . . ?
C1 C2 C7 N4 3.7(9) . . . . ?
O3 N4 C7 C6 171.3(5) . . . . ?
O4 N4 C7 C6 -9.5(8) . . . . ?
O3 N4 C7 C2 -10.6(7) . . . . ?
O4 N4 C7 C2 168.7(5) . . . . ?
N7 N6 C8 N5 -5.1(8) . . . . ?
N7 N6 C8 N2 177.1(4) . . . . ?
C3 N2 C8 N6 -2.5(8) . . . . ?
N1 N2 C8 N6 -175.2(5) . . . . ?
C3 N2 C8 N5 179.4(5) . . . . ?
N1 N2 C8 N5 6.8(7) . . . . ?
N6 N7 C9 C10 179.0(5) . . . . ?
N7 C9 C10 C11 25.8(8) . . . . ?
N7 C9 C10 C15 -154.7(6) . . . . ?
C15 C10 C11 C12 2.4(8) . . . . ?
C9 C10 C11 C12 -178.1(5) . . . . ?
C15 C10 C11 N8 -172.9(5) . . . . ?
C9 C10 C11 N8 6.7(8) . . . . ?
O6 N8 C11 C12 69.5(7) . . . . ?
O5 N8 C11 C12 -109.5(5) . . . . ?
O6 N8 C11 C10 -114.8(5) . . . . ?
O5 N8 C11 C10 66.2(7) . . . . ?
C10 C11 C12 C13 -3.4(9) . . . . ?
N8 C11 C12 C13 172.0(5) . . . . ?
C11 C12 C13 C14 1.5(9) . . . . ?
C11 C12 C13 N9 -177.6(5) . . . . ?
O7 N9 C13 C14 176.7(9) . . . . ?
O8 N9 C13 C14 -11.6(10) . . . . ?
O7 N9 C13 C12 -4.1(12) . . . . ?
O8 N9 C13 C12 167.6(7) . . . . ?
C12 C13 C14 C15 1.1(9) . . . . ?
N9 C13 C14 C15 -179.8(5) . . . . ?
C13 C14 C15 C10 -2.1(8) . . . . ?
C13 C14 C15 N10 177.1(5) . . . . ?
C11 C10 C15 C14 0.5(8) . . . . ?
C9 C10 C15 C14 -179.0(5) . . . . ?
C11 C10 C15 N10 -178.7(4) . . . . ?
C9 C10 C15 N10 1.7(8) . . . . ?
O10 N10 C15 C14 -142.1(5) . . . . ?
O9 N10 C15 C14 37.0(7) . . . . ?
O10 N10 C15 C10 37.2(7) . . . . ?
O9 N10 C15 C10 -143.7(6) . . . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 996729'
