# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 994771'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N10 O13'
_chemical_formula_sum            'C6 H6 N10 O13'
_chemical_formula_weight         426.21
_chemical_absolute_configuration unk

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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'

_cell_length_a                   11.757(2)
_cell_length_b                   12.192(2)
_cell_length_c                   21.542(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3087.8(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6760
_cell_measurement_theta_min      1.89
_cell_measurement_theta_max      27.84

_exptl_crystal_description       block
_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    1.834
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_T_max  0.9788
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31173
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.91
_reflns_number_total             4103
_reflns_number_gt                2439
_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)+(0.0353P)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       0.0166(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         4103
_refine_ls_number_parameters     536
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.034
_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 0.9179(3) 0.4056(3) 0.33777(14) 0.0752(9) Uani 1 1 d . . .
O2 O 0.9445(3) 0.2291(3) 0.33071(15) 0.0895(11) Uani 1 1 d . . .
O3 O 1.0493(3) 0.2491(2) 0.19638(16) 0.0770(9) Uani 1 1 d . . .
O4 O 0.9021(3) 0.1443(2) 0.20437(17) 0.0837(10) Uani 1 1 d . . .
O5 O 0.7114(3) 0.2889(3) 0.28512(14) 0.0711(9) Uani 1 1 d . . .
O6 O 0.7256(2) 0.3052(2) 0.18533(14) 0.0663(8) Uani 1 1 d . . .
O7 O 0.6827(2) 0.6004(2) 0.09958(11) 0.0543(7) Uani 1 1 d . . .
O8 O 0.8253(2) 0.9117(2) 0.20576(13) 0.0613(8) Uani 1 1 d . . .
O9 O 0.6754(3) 0.9603(3) 0.15455(14) 0.0846(10) Uani 1 1 d . . .
O10 O 0.5866(3) 1.0919(2) 0.2453(2) 0.0957(13) Uani 1 1 d . . .
O11 O 0.4733(3) 0.9740(2) 0.28525(14) 0.0680(9) Uani 1 1 d . . .
O12 O 0.7813(3) 1.0089(3) 0.31790(14) 0.0711(9) Uani 1 1 d . . .
O13 O 0.7240(3) 0.8512(2) 0.35202(13) 0.0692(9) Uani 1 1 d . . .
O14 O 0.3525(2) 0.7298(2) -0.09594(13) 0.0607(8) Uani 1 1 d . . .
O15 O 0.2336(2) 0.6533(2) -0.03206(16) 0.0747(10) Uani 1 1 d . . .
O16 O 0.4640(3) 0.5252(2) -0.04267(15) 0.0686(9) Uani 1 1 d . . .
O17 O 0.6033(2) 0.6357(2) -0.01872(13) 0.0553(7) Uani 1 1 d . . .
O18 O 0.4109(3) 0.5666(3) 0.08282(15) 0.0826(10) Uani 1 1 d . . .
O19 O 0.3003(4) 0.7087(3) 0.08626(16) 0.1037(14) Uani 1 1 d . . .
O20 O 0.3708(3) 1.0037(2) 0.15829(12) 0.0599(8) Uani 1 1 d . . .
O21 O 0.0056(3) 1.3586(2) 0.05363(16) 0.0757(9) Uani 1 1 d . . .
O22 O 0.1382(3) 1.4624(2) 0.01761(18) 0.0918(12) Uani 1 1 d . . .
O23 O 0.3346(2) 1.3161(2) 0.01912(13) 0.0644(8) Uani 1 1 d . . .
O24 O 0.2862(3) 1.3127(3) -0.07704(15) 0.0835(10) Uani 1 1 d . . .
O25 O 0.0335(3) 1.3201(3) -0.08755(15) 0.0806(10) Uani 1 1 d . . .
O26 O 0.0793(2) 1.1486(2) -0.07494(13) 0.0608(8) Uani 1 1 d . . .
N1 N 0.9212(3) 0.3198(3) 0.30982(16) 0.0575(9) Uani 1 1 d . . .
N2 N 0.9517(3) 0.2296(3) 0.21141(17) 0.0554(9) Uani 1 1 d . . .
N3 N 0.7638(3) 0.3031(2) 0.23768(16) 0.0469(7) Uani 1 1 d . . .
N4 N 0.8422(3) 0.5212(2) 0.22749(14) 0.0434(7) Uani 1 1 d D . .
H4 H 0.850(3) 0.552(3) 0.2618(12) 0.052 Uiso 1 1 d D . .
N5 N 0.7660(3) 0.5343(2) 0.12653(14) 0.0465(8) Uani 1 1 d . . .
N6 N 0.6370(3) 0.6747(2) 0.14268(15) 0.0486(8) Uani 1 1 d . . .
N7 N 0.6787(3) 0.7121(2) 0.24802(14) 0.0396(7) Uani 1 1 d D . .
H7 H 0.697(3) 0.676(3) 0.2793(12) 0.047 Uiso 1 1 d D . .
N8 N 0.7244(3) 0.9321(2) 0.20073(15) 0.0466(8) Uani 1 1 d . . .
N9 N 0.5617(3) 1.0019(3) 0.26299(17) 0.0504(8) Uani 1 1 d . . .
N10 N 0.7269(3) 0.9246(3) 0.31435(15) 0.0456(8) Uani 1 1 d . . .
N11 N 0.3239(3) 0.6925(2) -0.04607(16) 0.0448(7) Uani 1 1 d . . .
N12 N 0.5035(3) 0.6106(3) -0.02158(14) 0.0442(8) Uani 1 1 d . . .
N13 N 0.3726(3) 0.6522(3) 0.06276(16) 0.0556(9) Uani 1 1 d . . .
N14 N 0.3849(2) 0.8947(2) 0.00929(14) 0.0383(7) Uani 1 1 d D . .
H14 H 0.371(3) 0.928(3) -0.0240(13) 0.046 Uiso 1 1 d D . .
N15 N 0.4149(3) 0.9284(2) 0.11565(14) 0.0511(8) Uani 1 1 d . . .
N16 N 0.2922(3) 1.0736(2) 0.12974(14) 0.0468(8) Uani 1 1 d . . .
N17 N 0.2277(3) 1.0938(2) 0.02592(13) 0.0380(7) Uani 1 1 d D . .
H17 H 0.204(3) 1.051(2) -0.0021(13) 0.046 Uiso 1 1 d D . .
N18 N 0.0920(3) 1.3746(3) 0.02521(16) 0.0541(9) Uani 1 1 d . . .
N19 N 0.2679(3) 1.3041(3) -0.02249(16) 0.0464(8) Uani 1 1 d . . .
N20 N 0.0800(3) 1.2448(3) -0.06035(15) 0.0507(8) Uani 1 1 d . . .
C1 C 0.8907(3) 0.3251(3) 0.24148(16) 0.0401(8) Uani 1 1 d . . .
C2 C 0.9218(3) 0.4346(3) 0.21141(18) 0.0442(9) Uani 1 1 d . . .
H2A H 0.9975 0.4558 0.2246 0.053 Uiso 1 1 calc R . .
H2B H 0.9231 0.4257 0.1667 0.053 Uiso 1 1 calc R . .
C3 C 0.7723(3) 0.5667(3) 0.18423(16) 0.0361(8) Uani 1 1 d . . .
C4 C 0.6923(3) 0.6547(2) 0.19428(16) 0.0345(8) Uani 1 1 d . . .
C5 C 0.5952(3) 0.7983(3) 0.25311(17) 0.0417(8) Uani 1 1 d . . .
H5A H 0.5491 0.7862 0.2898 0.050 Uiso 1 1 calc R . .
H5B H 0.5453 0.7961 0.2172 0.050 Uiso 1 1 calc R . .
C6 C 0.6510(3) 0.9105(3) 0.25714(15) 0.0352(8) Uani 1 1 d . . .
C7 C 0.4190(3) 0.6947(3) 0.00186(15) 0.0357(8) Uani 1 1 d . . .
C8 C 0.4706(3) 0.8099(3) 0.00639(17) 0.0378(8) Uani 1 1 d . . .
H8A H 0.5180 0.8141 0.0432 0.045 Uiso 1 1 calc R . .
H8B H 0.5188 0.8227 -0.0294 0.045 Uiso 1 1 calc R . .
C9 C 0.3658(3) 0.9516(3) 0.06360(16) 0.0345(8) Uani 1 1 d . . .
C10 C 0.2895(3) 1.0427(3) 0.07177(15) 0.0351(8) Uani 1 1 d . . .
C11 C 0.1490(3) 1.1802(3) 0.04483(16) 0.0387(8) Uani 1 1 d . . .
H11A H 0.1715 1.2084 0.0851 0.046 Uiso 1 1 calc R . .
H11B H 0.0730 1.1499 0.0487 0.046 Uiso 1 1 calc R . .
C12 C 0.1476(3) 1.2733(3) -0.00201(16) 0.0372(8) 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 1.207(4) . ?
O2 N1 1.225(4) . ?
O3 N2 1.215(4) . ?
O4 N2 1.203(4) . ?
O5 N3 1.206(4) . ?
O6 N3 1.214(4) . ?
O7 N5 1.395(4) . ?
O7 N6 1.404(4) . ?
O8 N8 1.216(4) . ?
O9 N8 1.200(4) . ?
O10 N9 1.198(4) . ?
O11 N9 1.194(4) . ?
O12 N10 1.212(4) . ?
O13 N10 1.209(4) . ?
O14 N11 1.214(4) . ?
O15 N11 1.203(4) . ?
O16 N12 1.226(4) . ?
O17 N12 1.214(4) . ?
O18 N13 1.216(4) . ?
O19 N13 1.206(4) . ?
O20 N16 1.399(4) . ?
O20 N15 1.399(4) . ?
O21 N18 1.202(4) . ?
O22 N18 1.211(4) . ?
O23 N19 1.200(4) . ?
O24 N19 1.199(4) . ?
O25 N20 1.218(4) . ?
O26 N20 1.214(4) . ?
N1 C1 1.517(5) . ?
N2 C1 1.513(5) . ?
N3 C1 1.518(5) . ?
N4 C3 1.361(4) . ?
N4 C2 1.453(4) . ?
N4 H4 0.83(2) . ?
N5 C3 1.307(4) . ?
N6 C4 1.311(4) . ?
N7 C4 1.362(4) . ?
N7 C5 1.442(4) . ?
N7 H7 0.83(2) . ?
N8 C6 1.513(4) . ?
N9 C6 1.536(4) . ?
N10 C6 1.531(4) . ?
N11 C7 1.523(4) . ?
N12 C7 1.515(4) . ?
N13 C7 1.513(5) . ?
N14 C9 1.379(4) . ?
N14 C8 1.445(4) . ?
N14 H14 0.84(2) . ?
N15 C9 1.293(4) . ?
N16 C10 1.305(4) . ?
N17 C10 1.376(4) . ?
N17 C11 1.460(4) . ?
N17 H17 0.84(2) . ?
N18 C12 1.515(5) . ?
N19 C12 1.529(5) . ?
N20 C12 1.527(5) . ?
C1 C2 1.528(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.443(4) . ?
C5 C6 1.520(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C8 1.533(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.438(5) . ?
C11 C12 1.519(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
N5 O7 N6 111.5(2) . . ?
N16 O20 N15 110.9(2) . . ?
O1 N1 O2 127.3(4) . . ?
O1 N1 C1 116.1(3) . . ?
O2 N1 C1 116.6(4) . . ?
O4 N2 O3 126.4(4) . . ?
O4 N2 C1 119.3(3) . . ?
O3 N2 C1 114.3(3) . . ?
O5 N3 O6 127.0(3) . . ?
O5 N3 C1 118.8(3) . . ?
O6 N3 C1 114.2(3) . . ?
C3 N4 C2 121.5(3) . . ?
C3 N4 H4 119(3) . . ?
C2 N4 H4 118(3) . . ?
C3 N5 O7 105.1(3) . . ?
C4 N6 O7 104.6(3) . . ?
C4 N7 C5 121.2(3) . . ?
C4 N7 H7 113(2) . . ?
C5 N7 H7 120(3) . . ?
O9 N8 O8 126.9(4) . . ?
O9 N8 C6 116.2(3) . . ?
O8 N8 C6 116.7(3) . . ?
O11 N9 O10 126.9(3) . . ?
O11 N9 C6 114.9(3) . . ?
O10 N9 C6 118.2(3) . . ?
O12 N10 O13 126.9(3) . . ?
O12 N10 C6 116.9(3) . . ?
O13 N10 C6 116.1(3) . . ?
O15 N11 O14 128.0(3) . . ?
O15 N11 C7 119.0(3) . . ?
O14 N11 C7 112.9(3) . . ?
O17 N12 O16 126.8(3) . . ?
O17 N12 C7 116.4(3) . . ?
O16 N12 C7 116.7(3) . . ?
O19 N13 O18 127.1(4) . . ?
O19 N13 C7 115.0(3) . . ?
O18 N13 C7 118.0(3) . . ?
C9 N14 C8 120.7(3) . . ?
C9 N14 H14 117(2) . . ?
C8 N14 H14 116(3) . . ?
C9 N15 O20 105.1(3) . . ?
C10 N16 O20 105.1(3) . . ?
C10 N17 C11 117.5(3) . . ?
C10 N17 H17 114(2) . . ?
C11 N17 H17 116(2) . . ?
O21 N18 O22 126.2(3) . . ?
O21 N18 C12 115.4(3) . . ?
O22 N18 C12 118.3(3) . . ?
O23 N19 O24 127.2(3) . . ?
O23 N19 C12 114.8(3) . . ?
O24 N19 C12 118.0(3) . . ?
O26 N20 O25 126.8(4) . . ?
O26 N20 C12 115.9(3) . . ?
O25 N20 C12 117.3(3) . . ?
N2 C1 N3 107.9(3) . . ?
N2 C1 N1 105.7(3) . . ?
N3 C1 N1 106.1(3) . . ?
N2 C1 C2 112.1(3) . . ?
N3 C1 C2 111.5(3) . . ?
N1 C1 C2 113.1(3) . . ?
N4 C2 C1 112.3(3) . . ?
N4 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N4 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
N5 C3 N4 124.2(3) . . ?
N5 C3 C4 109.3(3) . . ?
N4 C3 C4 126.4(3) . . ?
N6 C4 N7 124.6(3) . . ?
N6 C4 C3 109.5(3) . . ?
N7 C4 C3 125.9(3) . . ?
N7 C5 C6 111.5(3) . . ?
N7 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N7 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N8 C6 C5 110.9(3) . . ?
N8 C6 N10 107.1(3) . . ?
C5 C6 N10 113.5(3) . . ?
N8 C6 N9 109.2(3) . . ?
C5 C6 N9 111.2(3) . . ?
N10 C6 N9 104.5(2) . . ?
N13 C7 N12 107.1(3) . . ?
N13 C7 N11 108.5(3) . . ?
N12 C7 N11 104.1(3) . . ?
N13 C7 C8 113.7(3) . . ?
N12 C7 C8 112.5(3) . . ?
N11 C7 C8 110.5(3) . . ?
N14 C8 C7 112.5(3) . . ?
N14 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N14 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N15 C9 N14 123.6(3) . . ?
N15 C9 C10 110.0(3) . . ?
N14 C9 C10 126.5(3) . . ?
N16 C10 N17 124.7(3) . . ?
N16 C10 C9 109.0(3) . . ?
N17 C10 C9 126.3(3) . . ?
N17 C11 C12 111.1(3) . . ?
N17 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N17 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N18 C12 C11 110.9(3) . . ?
N18 C12 N19 108.1(3) . . ?
C11 C12 N19 111.4(3) . . ?
N18 C12 N20 106.2(3) . . ?
C11 C12 N20 112.5(3) . . ?
N19 C12 N20 107.4(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
N6 O7 N5 C3 -0.3(4) . . . . ?
N5 O7 N6 C4 0.6(3) . . . . ?
N16 O20 N15 C9 0.2(4) . . . . ?
N15 O20 N16 C10 -0.6(4) . . . . ?
O4 N2 C1 N3 -18.5(5) . . . . ?
O3 N2 C1 N3 161.3(4) . . . . ?
O4 N2 C1 N1 94.6(4) . . . . ?
O3 N2 C1 N1 -85.6(4) . . . . ?
O4 N2 C1 C2 -141.7(4) . . . . ?
O3 N2 C1 C2 38.1(5) . . . . ?
O5 N3 C1 N2 114.6(4) . . . . ?
O6 N3 C1 N2 -67.5(4) . . . . ?
O5 N3 C1 N1 1.7(5) . . . . ?
O6 N3 C1 N1 179.6(3) . . . . ?
O5 N3 C1 C2 -121.9(4) . . . . ?
O6 N3 C1 C2 56.1(4) . . . . ?
O1 N1 C1 N2 153.9(4) . . . . ?
O2 N1 C1 N2 -27.3(5) . . . . ?
O1 N1 C1 N3 -91.7(4) . . . . ?
O2 N1 C1 N3 87.0(4) . . . . ?
O1 N1 C1 C2 30.8(5) . . . . ?
O2 N1 C1 C2 -150.4(4) . . . . ?
C3 N4 C2 C1 -112.6(4) . . . . ?
N2 C1 C2 N4 164.0(3) . . . . ?
N3 C1 C2 N4 42.9(4) . . . . ?
N1 C1 C2 N4 -76.6(4) . . . . ?
O7 N5 C3 N4 178.4(3) . . . . ?
O7 N5 C3 C4 -0.2(4) . . . . ?
C2 N4 C3 N5 3.5(5) . . . . ?
C2 N4 C3 C4 -178.2(3) . . . . ?
O7 N6 C4 N7 176.8(3) . . . . ?
O7 N6 C4 C3 -0.7(3) . . . . ?
C5 N7 C4 N6 3.4(5) . . . . ?
C5 N7 C4 C3 -179.5(3) . . . . ?
N5 C3 C4 N6 0.6(4) . . . . ?
N4 C3 C4 N6 -177.9(3) . . . . ?
N5 C3 C4 N7 -176.9(3) . . . . ?
N4 C3 C4 N7 4.6(5) . . . . ?
C4 N7 C5 C6 -109.8(3) . . . . ?
O9 N8 C6 C5 79.4(4) . . . . ?
O8 N8 C6 C5 -95.7(3) . . . . ?
O9 N8 C6 N10 -156.3(3) . . . . ?
O8 N8 C6 N10 28.7(4) . . . . ?
O9 N8 C6 N9 -43.6(4) . . . . ?
O8 N8 C6 N9 141.4(3) . . . . ?
N7 C5 C6 N8 58.6(4) . . . . ?
N7 C5 C6 N10 -62.1(4) . . . . ?
N7 C5 C6 N9 -179.6(3) . . . . ?
O12 N10 C6 N8 51.5(4) . . . . ?
O13 N10 C6 N8 -130.2(3) . . . . ?
O12 N10 C6 C5 174.2(3) . . . . ?
O13 N10 C6 C5 -7.5(4) . . . . ?
O12 N10 C6 N9 -64.4(4) . . . . ?
O13 N10 C6 N9 113.9(3) . . . . ?
O11 N9 C6 N8 148.4(3) . . . . ?
O10 N9 C6 N8 -31.6(5) . . . . ?
O11 N9 C6 C5 25.6(4) . . . . ?
O10 N9 C6 C5 -154.4(4) . . . . ?
O11 N9 C6 N10 -97.2(4) . . . . ?
O10 N9 C6 N10 82.8(4) . . . . ?
O19 N13 C7 N12 -177.3(3) . . . . ?
O18 N13 C7 N12 2.9(4) . . . . ?
O19 N13 C7 N11 -65.5(4) . . . . ?
O18 N13 C7 N11 114.6(4) . . . . ?
O19 N13 C7 C8 57.9(4) . . . . ?
O18 N13 C7 C8 -122.0(3) . . . . ?
O17 N12 C7 N13 -107.8(3) . . . . ?
O16 N12 C7 N13 73.8(4) . . . . ?
O17 N12 C7 N11 137.5(3) . . . . ?
O16 N12 C7 N11 -40.9(4) . . . . ?
O17 N12 C7 C8 17.8(4) . . . . ?
O16 N12 C7 C8 -160.6(3) . . . . ?
O15 N11 C7 N13 -4.8(4) . . . . ?
O14 N11 C7 N13 177.0(3) . . . . ?
O15 N11 C7 N12 108.9(3) . . . . ?
O14 N11 C7 N12 -69.2(3) . . . . ?
O15 N11 C7 C8 -130.1(3) . . . . ?
O14 N11 C7 C8 51.8(4) . . . . ?
C9 N14 C8 C7 108.7(3) . . . . ?
N13 C7 C8 N14 -76.5(4) . . . . ?
N12 C7 C8 N14 161.6(3) . . . . ?
N11 C7 C8 N14 45.7(4) . . . . ?
O20 N15 C9 N14 -179.1(3) . . . . ?
O20 N15 C9 C10 0.2(4) . . . . ?
C8 N14 C9 N15 -5.6(5) . . . . ?
C8 N14 C9 C10 175.2(3) . . . . ?
O20 N16 C10 N17 -176.1(3) . . . . ?
O20 N16 C10 C9 0.7(4) . . . . ?
C11 N17 C10 N16 -7.9(5) . . . . ?
C11 N17 C10 C9 175.9(3) . . . . ?
N15 C9 C10 N16 -0.6(4) . . . . ?
N14 C9 C10 N16 178.7(3) . . . . ?
N15 C9 C10 N17 176.1(3) . . . . ?
N14 C9 C10 N17 -4.6(5) . . . . ?
C10 N17 C11 C12 142.3(3) . . . . ?
O21 N18 C12 C11 -44.3(4) . . . . ?
O22 N18 C12 C11 134.5(4) . . . . ?
O21 N18 C12 N19 -166.8(3) . . . . ?
O22 N18 C12 N19 12.0(5) . . . . ?
O21 N18 C12 N20 78.2(4) . . . . ?
O22 N18 C12 N20 -103.0(4) . . . . ?
N17 C11 C12 N18 -164.8(3) . . . . ?
N17 C11 C12 N19 -44.3(4) . . . . ?
N17 C11 C12 N20 76.4(4) . . . . ?
O23 N19 C12 N18 74.1(4) . . . . ?
O24 N19 C12 N18 -106.5(4) . . . . ?
O23 N19 C12 C11 -48.0(4) . . . . ?
O24 N19 C12 C11 131.4(4) . . . . ?
O23 N19 C12 N20 -171.7(3) . . . . ?
O24 N19 C12 N20 7.7(5) . . . . ?
O26 N20 C12 N18 -151.9(3) . . . . ?
O25 N20 C12 N18 28.6(4) . . . . ?
O26 N20 C12 C11 -30.4(4) . . . . ?
O25 N20 C12 C11 150.1(3) . . . . ?
O26 N20 C12 N19 92.6(4) . . . . ?
O25 N20 C12 N19 -86.9(4) . . . . ?

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
N17 H17 O26 0.84(2) 2.46(3) 2.866(4) 111(3) .
N14 H14 O7 0.84(2) 2.77(3) 3.340(4) 126(3) 4_465
N14 H14 N5 0.84(2) 2.57(3) 3.356(4) 156(3) 4_465
N7 H7 N16 0.83(2) 2.33(2) 3.146(4) 168(4) 3_645
N4 H4 O1 0.83(2) 2.55(4) 2.902(4) 107(3) .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.056
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 994772'
_audit_update_record             
;
2014-04-01 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 N14 O14, C H2 Cl2'
_chemical_formula_sum            'C9 H8 Cl2 N14 O14'
_chemical_formula_weight         607.19

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '
_symmetry_space_group_name_Hall  '-C 2yc  '

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

_cell_length_a                   17.826(4)
_cell_length_b                   12.307(3)
_cell_length_c                   10.724(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.339(5)
_cell_angle_gamma                90.00
_cell_volume                     2233.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    617
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      21.40

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8650
_exptl_absorpt_correction_T_max  0.9544
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4583
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2194
_reflns_number_gt                1252
_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)+(0.0303P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2194
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.07745(16) 0.4637(2) -0.0582(2) 0.0164(7) Uani 1 1 d . . .
C2 C 0.12928(17) 0.3855(2) 0.0235(3) 0.0177(7) Uani 1 1 d . . .
C3 C 0.19140(17) 0.2814(2) 0.2211(3) 0.0231(7) Uani 1 1 d . . .
H3A H 0.2174 0.3240 0.3014 0.028 Uiso 1 1 calc R . .
H3B H 0.2305 0.2689 0.1745 0.028 Uiso 1 1 calc R . .
C4 C 0.16430(17) 0.1732(2) 0.2590(3) 0.0200(7) Uani 1 1 d . . .
C5 C 0.0000 0.1503(4) 0.7500 0.0441(14) Uani 1 2 d S . .
H5A H -0.0382 0.1030 0.6860 0.053 Uiso 0.50 1 calc PR . .
H5B H 0.0382 0.1030 0.8140 0.053 Uiso 0.50 1 calc PR . .
Cl1 Cl 0.05044(7) 0.22997(9) 0.66736(10) 0.0638(4) Uani 1 1 d . . .
N1 N 0.00920(14) 0.51629(19) -0.04933(19) 0.0179(6) Uani 1 1 d . . .
N2 N 0.10147(14) 0.4878(2) -0.1574(2) 0.0260(6) Uani 1 1 d . . .
N3 N 0.18428(15) 0.3619(2) -0.0285(2) 0.0270(7) Uani 1 1 d . . .
N4 N 0.12502(13) 0.34228(19) 0.1372(2) 0.0192(6) Uani 1 1 d . . .
H4 H 0.0821 0.3511 0.1600 0.023 Uiso 1 1 calc R . .
N5 N 0.10821(16) 0.1161(2) 0.1410(2) 0.0291(7) Uani 1 1 d . . .
N6 N 0.23315(17) 0.0966(2) 0.3179(3) 0.0304(7) Uani 1 1 d . . .
N7 N 0.12283(16) 0.1828(2) 0.3627(2) 0.0287(7) Uani 1 1 d . . .
O1 O 0.16708(13) 0.42697(18) -0.14200(18) 0.0312(6) Uani 1 1 d . . .
O2 O 0.13083(14) 0.11439(18) 0.0454(2) 0.0375(6) Uani 1 1 d . . .
O3 O 0.04766(13) 0.0780(2) 0.1512(2) 0.0443(7) Uani 1 1 d . . .
O4 O 0.22526(14) 0.0027(2) 0.2806(2) 0.0416(6) Uani 1 1 d . . .
O5 O 0.28976(14) 0.1373(2) 0.3974(2) 0.0454(7) Uani 1 1 d . . .
O6 O 0.07966(13) 0.26074(19) 0.3522(2) 0.0353(6) Uani 1 1 d . . .
O7 O 0.13685(17) 0.1135(2) 0.4472(2) 0.0607(9) 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 N2 1.300(3) . ?
C1 N1 1.407(3) . ?
C1 C2 1.427(4) . ?
C2 N3 1.304(3) . ?
C2 N4 1.354(3) . ?
C3 N4 1.450(3) . ?
C3 C4 1.515(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N5 1.516(4) . ?
C4 N6 1.519(4) . ?
C4 N7 1.521(3) . ?
C5 Cl1 1.748(3) 2_556 ?
C5 Cl1 1.748(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N1 N1 1.267(4) 5_565 ?
N2 O1 1.355(3) . ?
N3 O1 1.408(3) . ?
N4 H4 0.8800 . ?
N5 O3 1.213(3) . ?
N5 O2 1.215(3) . ?
N6 O5 1.207(3) . ?
N6 O4 1.216(3) . ?
N7 O7 1.212(3) . ?
N7 O6 1.212(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
N2 C1 N1 117.7(3) . . ?
N2 C1 C2 109.9(3) . . ?
N1 C1 C2 132.4(3) . . ?
N3 C2 N4 124.1(3) . . ?
N3 C2 C1 108.5(2) . . ?
N4 C2 C1 127.5(3) . . ?
N4 C3 C4 110.7(2) . . ?
N4 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 N5 111.5(2) . . ?
C3 C4 N6 111.9(2) . . ?
N5 C4 N6 107.1(2) . . ?
C3 C4 N7 113.4(2) . . ?
N5 C4 N7 107.5(2) . . ?
N6 C4 N7 105.0(2) . . ?
Cl1 C5 Cl1 111.8(3) 2_556 . ?
Cl1 C5 H5A 109.3 2_556 . ?
Cl1 C5 H5A 109.3 . . ?
Cl1 C5 H5B 109.3 2_556 . ?
Cl1 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N1 N1 C1 111.5(3) 5_565 . ?
C1 N2 O1 105.5(2) . . ?
C2 N3 O1 104.7(2) . . ?
C2 N4 C3 119.7(2) . . ?
C2 N4 H4 120.1 . . ?
C3 N4 H4 120.1 . . ?
O3 N5 O2 127.6(3) . . ?
O3 N5 C4 118.5(2) . . ?
O2 N5 C4 113.9(3) . . ?
O5 N6 O4 127.7(3) . . ?
O5 N6 C4 115.0(3) . . ?
O4 N6 C4 117.3(3) . . ?
O7 N7 O6 127.0(3) . . ?
O7 N7 C4 117.3(3) . . ?
O6 N7 C4 115.7(2) . . ?
N2 O1 N3 111.41(19) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.072
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 994774'
_audit_update_record             
;
2014-04-01 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 N16 O18'
_chemical_formula_sum            'C8 H4 N16 O18'
_chemical_formula_weight         612.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   7.6324(7)
_cell_length_b                   9.7348(10)
_cell_length_c                   14.8237(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.562(3)
_cell_angle_gamma                90.00
_cell_volume                     1089.12(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1253
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      24.51

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6347
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         25.75
_reflns_number_total             2048
_reflns_number_gt                1285
_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)+(0.0227P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2048
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0734
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.5328(3) 0.6758(2) 0.49412(15) 0.0209(6) Uani 1 1 d . . .
C2 C 0.4680(3) 0.7356(2) 0.40776(14) 0.0187(5) Uani 1 1 d . . .
C3 C 0.4216(3) 0.7149(2) 0.23860(14) 0.0182(5) Uani 1 1 d . . .
H3A H 0.4775 0.8069 0.2431 0.022 Uiso 1 1 calc R . .
H3B H 0.3099 0.7213 0.1953 0.022 Uiso 1 1 calc R . .
C4 C 0.5459(3) 0.6124(2) 0.20193(14) 0.0199(5) Uani 1 1 d . . .
N1 N 0.6163(3) 0.7704(2) 0.54613(13) 0.0309(5) Uani 1 1 d . . .
N2 N 0.5133(3) 0.8643(2) 0.40806(12) 0.0283(5) Uani 1 1 d . . .
N3 N 0.5293(2) 0.54325(19) 0.53022(12) 0.0254(5) Uani 1 1 d . . .
N4 N 0.3817(2) 0.67440(18) 0.32779(11) 0.0175(4) Uani 1 1 d . . .
N5 N 0.2095(2) 0.62181(19) 0.33304(13) 0.0230(5) Uani 1 1 d . . .
N6 N 0.4527(3) 0.4797(2) 0.16726(15) 0.0284(5) Uani 1 1 d . . .
N7 N 0.6213(3) 0.6764(2) 0.12227(14) 0.0287(5) Uani 1 1 d . . .
N8 N 0.7038(2) 0.5717(2) 0.27194(14) 0.0260(5) Uani 1 1 d . . .
O1 O 0.6091(2) 0.88683(17) 0.49388(11) 0.0358(5) Uani 1 1 d . . .
O2 O 0.1238(2) 0.58446(16) 0.26127(11) 0.0309(4) Uani 1 1 d . . .
O3 O 0.1682(2) 0.61749(17) 0.40860(11) 0.0302(4) Uani 1 1 d . . .
O4 O 0.3946(2) 0.41210(16) 0.22487(13) 0.0385(5) Uani 1 1 d . . .
O5 O 0.4416(3) 0.45418(19) 0.08740(13) 0.0581(6) Uani 1 1 d . . .
O6 O 0.5233(2) 0.75473(19) 0.07553(11) 0.0436(5) Uani 1 1 d . . .
O7 O 0.7699(3) 0.6448(2) 0.11251(13) 0.0532(6) Uani 1 1 d . . .
O8 O 0.7654(2) 0.66476(18) 0.32126(11) 0.0373(5) Uani 1 1 d . . .
O9 O 0.7544(2) 0.45403(17) 0.27183(13) 0.0441(5) 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 N1 1.304(3) . ?
C1 N3 1.399(3) . ?
C1 C2 1.426(3) . ?
C2 N2 1.299(3) . ?
C2 N4 1.401(3) . ?
C3 N4 1.455(3) . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N8 1.521(3) . ?
C4 N7 1.522(3) . ?
C4 N6 1.527(3) . ?
N1 O1 1.369(2) . ?
N2 O1 1.387(2) . ?
N3 N3 1.262(3) 3_666 ?
N4 N5 1.424(2) . ?
N5 O3 1.208(2) . ?
N5 O2 1.218(2) . ?
N6 O5 1.200(2) . ?
N6 O4 1.213(2) . ?
N7 O7 1.204(2) . ?
N7 O6 1.211(2) . ?
N8 O9 1.209(2) . ?
N8 O8 1.214(2) . ?

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
N1 C1 N3 117.43(18) . . ?
N1 C1 C2 108.4(2) . . ?
N3 C1 C2 134.11(19) . . ?
N2 C2 N4 120.31(19) . . ?
N2 C2 C1 109.50(18) . . ?
N4 C2 C1 130.0(2) . . ?
N4 C3 C4 111.76(17) . . ?
N4 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N4 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
N8 C4 N7 106.47(17) . . ?
N8 C4 N6 106.93(18) . . ?
N7 C4 N6 107.24(17) . . ?
N8 C4 C3 113.41(17) . . ?
N7 C4 C3 109.55(18) . . ?
N6 C4 C3 112.87(18) . . ?
C1 N1 O1 105.96(17) . . ?
C2 N2 O1 105.04(17) . . ?
N3 N3 C1 111.7(2) 3_666 . ?
C2 N4 N5 115.35(17) . . ?
C2 N4 C3 121.22(18) . . ?
N5 N4 C3 117.84(16) . . ?
O3 N5 O2 128.3(2) . . ?
O3 N5 N4 115.67(17) . . ?
O2 N5 N4 116.05(18) . . ?
O5 N6 O4 127.1(2) . . ?
O5 N6 C4 117.9(2) . . ?
O4 N6 C4 115.01(19) . . ?
O7 N7 O6 127.2(2) . . ?
O7 N7 C4 117.4(2) . . ?
O6 N7 C4 115.4(2) . . ?
O9 N8 O8 127.77(19) . . ?
O9 N8 C4 117.84(19) . . ?
O8 N8 C4 114.38(18) . . ?
N1 O1 N2 111.04(16) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.75
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.059
