# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_bo2440

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 N10 O8'
_chemical_formula_weight         346.21

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.124(2)
_cell_length_b                   8.642(3)
_cell_length_c                   10.941(4)
_cell_angle_alpha                100.173(2)
_cell_angle_beta                 106.167(4)
_cell_angle_gamma                102.307(4)
_cell_volume                     611.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1840
_cell_measurement_theta_min      2.492
_cell_measurement_theta_max      29.123

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9201
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8629
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0519
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         29.12
_reflns_number_total             3204
_reflns_number_gt                2251
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0485P)²+0.1160P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3204
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6544(2) -0.10368(15) 0.76313(13) 0.0255(3) Uani 1 1 d . . .
O2 O 0.52105(19) 0.08169(15) 0.83593(12) 0.0246(3) Uani 1 1 d . . .
O3 O 0.7928(2) 0.40993(16) 0.40469(13) 0.0287(3) Uani 1 1 d . . .
O4 O 0.71603(19) 0.55357(15) 0.55850(14) 0.0282(3) Uani 1 1 d . . .
O5 O 0.23695(18) 0.19277(14) 0.63560(13) 0.0253(3) Uani 1 1 d . . .
O6 O 0.12329(18) 0.34906(15) 0.76092(13) 0.0245(3) Uani 1 1 d . . .
O7 O 1.0358(2) 0.80670(17) 1.00119(15) 0.0384(4) Uani 1 1 d . . .
O8 O 0.7811(2) 0.86099(15) 1.05675(13) 0.0274(3) Uani 1 1 d . . .
N1 N 0.7263(2) 0.04749(16) 0.58212(14) 0.0167(3) Uani 1 1 d . . .
N2 N 0.7565(2) 0.15343(16) 0.50922(14) 0.0166(3) Uani 1 1 d . . .
N3 N 0.6279(2) 0.40182(16) 0.76059(14) 0.0181(3) Uani 1 1 d . . .
N4 N 0.7908(2) 0.52704(17) 0.83387(15) 0.0228(3) Uani 1 1 d . . .
N5 N 0.3815(2) 0.65132(19) 0.91865(15) 0.0223(3) Uani 1 1 d . . .
N6 N 0.6114(2) 0.02673(16) 0.76513(14) 0.0175(3) Uani 1 1 d . . .
N7 N 0.7431(2) 0.42608(17) 0.50407(15) 0.0204(3) Uani 1 1 d . . .
N8 N 0.2609(2) 0.31560(16) 0.72120(14) 0.0181(3) Uani 1 1 d . . .
N9 N 0.8562(2) 0.77598(17) 0.99137(15) 0.0236(3) Uani 1 1 d . . .
N10 N 0.9775(3) 0.1245(2) 0.32566(17) 0.0208(3) Uani 1 1 d . . .
C1 C 0.6657(2) 0.11962(19) 0.67780(16) 0.0155(3) Uani 1 1 d . . .
C2 C 0.6574(2) 0.27687(19) 0.67087(16) 0.0162(3) Uani 1 1 d . . .
C3 C 0.7157(2) 0.28984(19) 0.56126(16) 0.0158(3) Uani 1 1 d . . .
C4 C 0.4526(2) 0.4276(2) 0.77987(16) 0.0169(3) Uani 1 1 d . . .
C5 C 0.5043(2) 0.57853(19) 0.87130(16) 0.0162(3) Uani 1 1 d . . .
C6 C 0.7169(3) 0.6298(2) 0.89918(17) 0.0195(4) Uani 1 1 d . . .
H10A H 0.908(4) 0.059(3) 0.243(3) 0.042(6) Uiso 1 1 d . . .
H10B H 0.890(4) 0.125(3) 0.374(3) 0.049(7) Uiso 1 1 d . . .
H5A H 0.234(3) 0.595(3) 0.899(2) 0.037(6) Uiso 1 1 d . . .
H10C H 1.086(4) 0.084(3) 0.361(3) 0.059(8) Uiso 1 1 d . . .
H10D H 1.034(3) 0.226(3) 0.318(2) 0.037(6) Uiso 1 1 d . . .
H5B H 0.447(4) 0.751(3) 0.977(3) 0.062(8) 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 N6 1.2275(18) . ?
O2 N6 1.2322(17) . ?
O3 N7 1.228(2) . ?
O4 N7 1.2364(18) . ?
O5 N8 1.2310(17) . ?
O6 N8 1.2441(17) . ?
O7 N9 1.2197(19) . ?
O8 N9 1.2378(18) . ?
N1 N2 1.338(2) . ?
N1 C1 1.344(2) . ?
N2 C3 1.341(2) . ?
N3 N4 1.3418(19) . ?
N3 C4 1.380(2) . ?
N3 C2 1.4182(19) . ?
N4 C6 1.327(2) . ?
N5 C5 1.342(2) . ?
N5 H5A 1.00(2) . ?
N5 H5B 0.91(3) . ?
N6 C1 1.432(2) . ?
N7 C3 1.430(2) . ?
N8 C4 1.394(2) . ?
N9 C6 1.434(2) . ?
N10 H10A 0.91(3) . ?
N10 H10B 0.92(3) . ?
N10 H10C 0.93(3) . ?
N10 H10D 0.91(2) . ?
C1 C2 1.387(2) . ?
C2 C3 1.389(2) . ?
C4 C5 1.402(2) . ?
C5 C6 1.411(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
N2 N1 C1 107.51(13) . . ?
N1 N2 C3 107.55(13) . . ?
N4 N3 C4 111.12(13) . . ?
N4 N3 C2 117.62(13) . . ?
C4 N3 C2 130.98(14) . . ?
C6 N4 N3 104.61(14) . . ?
C5 N5 H5A 122.5(12) . . ?
C5 N5 H5B 114.1(17) . . ?
H5A N5 H5B 123(2) . . ?
O1 N6 O2 124.16(15) . . ?
O1 N6 C1 118.11(13) . . ?
O2 N6 C1 117.72(14) . . ?
O3 N7 O4 124.00(15) . . ?
O3 N7 C3 118.31(14) . . ?
O4 N7 C3 117.68(15) . . ?
O5 N8 O6 124.31(14) . . ?
O5 N8 C4 119.74(14) . . ?
O6 N8 C4 115.95(13) . . ?
O7 N9 O8 125.13(15) . . ?
O7 N9 C6 119.16(14) . . ?
O8 N9 C6 115.70(15) . . ?
H10A N10 H10B 109(2) . . ?
H10A N10 H10C 107(2) . . ?
H10B N10 H10C 114(2) . . ?
H10A N10 H10D 108(2) . . ?
H10B N10 H10D 113.1(19) . . ?
H10C N10 H10D 106(2) . . ?
N1 C1 C2 111.76(15) . . ?
N1 C1 N6 118.37(14) . . ?
C2 C1 N6 129.80(14) . . ?
C1 C2 C3 101.33(13) . . ?
C1 C2 N3 130.22(16) . . ?
C3 C2 N3 127.86(15) . . ?
N2 C3 C2 111.84(14) . . ?
N2 C3 N7 118.98(14) . . ?
C2 C3 N7 129.13(14) . . ?
N3 C4 N8 124.15(14) . . ?
N3 C4 C5 108.36(14) . . ?
N8 C4 C5 127.42(15) . . ?
N5 C5 C4 128.43(16) . . ?
N5 C5 C6 130.38(15) . . ?
C4 C5 C6 101.18(14) . . ?
N4 C6 C5 114.72(14) . . ?
N4 C6 N9 118.46(15) . . ?
C5 C6 N9 126.79(15) . . ?

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 0.47(17) . . . . ?
C4 N3 N4 C6 0.4(2) . . . . ?
C2 N3 N4 C6 175.02(15) . . . . ?
N2 N1 C1 C2 -0.87(18) . . . . ?
N2 N1 C1 N6 176.32(13) . . . . ?
O1 N6 C1 N1 11.9(2) . . . . ?
O2 N6 C1 N1 -166.78(14) . . . . ?
O1 N6 C1 C2 -171.46(16) . . . . ?
O2 N6 C1 C2 9.8(2) . . . . ?
N1 C1 C2 C3 0.87(18) . . . . ?
N6 C1 C2 C3 -175.92(16) . . . . ?
N1 C1 C2 N3 -170.72(16) . . . . ?
N6 C1 C2 N3 12.5(3) . . . . ?
N4 N3 C2 C1 104.8(2) . . . . ?
C4 N3 C2 C1 -81.9(3) . . . . ?
N4 N3 C2 C3 -64.7(2) . . . . ?
C4 N3 C2 C3 108.6(2) . . . . ?
N1 N2 C3 C2 0.08(18) . . . . ?
N1 N2 C3 N7 177.84(13) . . . . ?
C1 C2 C3 N2 -0.57(18) . . . . ?
N3 C2 C3 N2 171.30(15) . . . . ?
C1 C2 C3 N7 -178.04(16) . . . . ?
N3 C2 C3 N7 -6.2(3) . . . . ?
O3 N7 C3 N2 3.8(2) . . . . ?
O4 N7 C3 N2 -175.84(14) . . . . ?
O3 N7 C3 C2 -178.87(16) . . . . ?
O4 N7 C3 C2 1.5(3) . . . . ?
N4 N3 C4 N8 -177.25(16) . . . . ?
C2 N3 C4 N8 9.1(3) . . . . ?
N4 N3 C4 C5 -0.1(2) . . . . ?
C2 N3 C4 C5 -173.74(17) . . . . ?
O5 N8 C4 N3 -8.3(3) . . . . ?
O6 N8 C4 N3 171.70(15) . . . . ?
O5 N8 C4 C5 175.06(16) . . . . ?
O6 N8 C4 C5 -4.9(3) . . . . ?
N3 C4 C5 N5 -179.84(17) . . . . ?
N8 C4 C5 N5 -2.8(3) . . . . ?
N3 C4 C5 C6 -0.27(18) . . . . ?
N8 C4 C5 C6 176.78(17) . . . . ?
N3 N4 C6 C5 -0.6(2) . . . . ?
N3 N4 C6 N9 177.75(15) . . . . ?
N5 C5 C6 N4 -179.88(18) . . . . ?
C4 C5 C6 N4 0.6(2) . . . . ?
N5 C5 C6 N9 1.9(3) . . . . ?
C4 C5 C6 N9 -177.65(17) . . . . ?
O7 N9 C6 N4 4.5(3) . . . . ?
O8 N9 C6 N4 -174.66(16) . . . . ?
O7 N9 C6 C5 -177.34(18) . . . . ?
O8 N9 C6 C5 3.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.064


_database_code_depnum_ccdc_archive 'CCDC 1014094'
#######################################################################
#
#                 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_bo2480

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H9 N15 O8'
_chemical_formula_weight         443.30

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

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                   13.012(3)
_cell_length_b                   6.3771(12)
_cell_length_c                   19.435(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.668(2)
_cell_angle_gamma                90.00
_cell_volume                     1612.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5699
_cell_measurement_theta_min      1.894
_cell_measurement_theta_max      29.131

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13543
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         29.14
_reflns_number_total             4245
_reflns_number_gt                3891
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0596P)²+0.5890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0076(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4245
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.71706(8) 1.12946(16) 0.44529(5) 0.0236(2) Uani 1 1 d . . .
O2 O 0.60869(7) 0.89598(16) 0.48120(5) 0.0236(2) Uani 1 1 d . . .
O3 O 0.89105(8) 0.92084(18) 0.75456(5) 0.0275(2) Uani 1 1 d . . .
O4 O 0.72826(8) 0.84675(17) 0.76087(5) 0.0259(2) Uani 1 1 d . . .
O5 O 0.37585(9) 1.07784(19) 0.73364(6) 0.0344(3) Uani 1 1 d . . .
O6 O 0.28733(7) 0.80913(19) 0.69673(5) 0.0290(3) Uani 1 1 d . . .
O7 O 0.71178(7) 0.51303(16) 0.56430(5) 0.0236(2) Uani 1 1 d . . .
O8 O 0.56765(8) 0.33898(16) 0.55371(6) 0.0285(2) Uani 1 1 d . . .
N1 N 0.16412(9) 0.4754(2) 0.55563(6) 0.0229(3) Uani 1 1 d . . .
N2 N 0.18150(9) 0.28772(19) 0.59127(6) 0.0229(2) Uani 1 1 d . . .
N3 N 0.03560(8) 0.44050(18) 0.62181(5) 0.0178(2) Uani 1 1 d . . .
N4 N -0.05374(9) 0.4980(2) 0.65668(6) 0.0211(2) Uani 1 1 d . . .
N5 N 0.03565(9) 0.7405(2) 0.54889(6) 0.0246(3) Uani 1 1 d . . .
N6 N 0.08654(9) 0.12692(19) 0.68143(6) 0.0212(2) Uani 1 1 d . . .
N7 N 0.83678(8) 1.06418(17) 0.55713(5) 0.0171(2) Uani 1 1 d . . .
N8 N 0.86957(8) 1.03367(18) 0.62256(5) 0.0174(2) Uani 1 1 d . . .
N9 N 0.60788(8) 0.83335(17) 0.63127(5) 0.0154(2) Uani 1 1 d . . .
N10 N 0.54048(8) 0.94710(18) 0.66626(5) 0.0180(2) Uani 1 1 d . . .
N11 N 0.39533(9) 0.4826(2) 0.62537(7) 0.0254(3) Uani 1 1 d . . .
N12 N 0.68471(8) 1.00831(18) 0.48859(5) 0.0173(2) Uani 1 1 d . . .
N13 N 0.80497(8) 0.90208(18) 0.72894(5) 0.0179(2) Uani 1 1 d . . .
N14 N 0.36709(9) 0.9124(2) 0.70144(6) 0.0230(3) Uani 1 1 d . . .
N15 N 0.61803(8) 0.49171(18) 0.57386(6) 0.0184(2) Uani 1 1 d . . .
C1 C 0.07713(10) 0.5661(2) 0.57338(6) 0.0191(3) Uani 1 1 d . . .
C2 C 0.10263(9) 0.2729(2) 0.63185(6) 0.0179(3) Uani 1 1 d . . .
C3 C 0.73975(9) 0.9953(2) 0.55297(6) 0.0154(2) Uani 1 1 d . . .
C4 C 0.70491(9) 0.9184(2) 0.61552(6) 0.0151(2) Uani 1 1 d . . .
C5 C 0.79136(9) 0.9484(2) 0.65709(6) 0.0152(2) Uani 1 1 d . . .
C6 C 0.45549(9) 0.8312(2) 0.66729(6) 0.0177(3) Uani 1 1 d . . .
C7 C 0.46398(9) 0.6366(2) 0.63290(6) 0.0175(3) Uani 1 1 d . . .
C8 C 0.56522(9) 0.6462(2) 0.60981(6) 0.0157(2) Uani 1 1 d . . .
H4A H -0.0395(16) 0.515(3) 0.7018(11) 0.041(5) Uiso 1 1 d . . .
H6A H 0.0218(16) 0.079(3) 0.6844(10) 0.033(5) Uiso 1 1 d . . .
H4B H -0.0983(14) 0.395(3) 0.6523(9) 0.028(5) Uiso 1 1 d . . .
H5A H -0.0178(17) 0.793(3) 0.5725(11) 0.042(5) Uiso 1 1 d . . .
H11A H 0.3368(17) 0.492(3) 0.6474(11) 0.042(6) Uiso 1 1 d . . .
H11B H 0.4138(16) 0.369(3) 0.6062(11) 0.039(6) Uiso 1 1 d . . .
H6B H 0.1307(16) 0.031(3) 0.6847(10) 0.033(5) Uiso 1 1 d . . .
H5B H 0.0750(16) 0.816(3) 0.5193(11) 0.040(5) Uiso 1 1 d . . .
H1 H 0.2056(16) 0.519(3) 0.5235(10) 0.036(5) 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 N12 1.2210(14) . ?
O2 N12 1.2283(14) . ?
O3 N13 1.2263(14) . ?
O4 N13 1.2331(14) . ?
O5 N14 1.2315(18) . ?
O6 N14 1.2314(16) . ?
O7 N15 1.2436(14) . ?
O8 N15 1.2352(15) . ?
N1 C1 1.3206(17) . ?
N1 N2 1.3997(18) . ?
N1 H1 0.88(2) . ?
N2 C2 1.3050(16) . ?
N3 C1 1.3533(16) . ?
N3 C2 1.3917(17) . ?
N3 N4 1.4013(14) . ?
N4 H4A 0.90(2) . ?
N4 H4B 0.88(2) . ?
N5 C1 1.3226(19) . ?
N5 H5A 0.90(2) . ?
N5 H5B 0.91(2) . ?
N6 C2 1.3580(17) . ?
N6 H6A 0.90(2) . ?
N6 H6B 0.84(2) . ?
N7 C3 1.3384(16) . ?
N7 N8 1.3507(14) . ?
N8 C5 1.3408(16) . ?
N9 N10 1.3310(14) . ?
N9 C8 1.3790(16) . ?
N9 C4 1.4111(15) . ?
N10 C6 1.3304(17) . ?
N11 C7 1.3347(18) . ?
N11 H11A 0.88(2) . ?
N11 H11B 0.85(2) . ?
N12 C3 1.4369(16) . ?
N13 C5 1.4362(16) . ?
N14 C6 1.4315(16) . ?
N15 C8 1.3935(16) . ?
C3 C4 1.3914(16) . ?
C4 C5 1.3905(16) . ?
C6 C7 1.4145(19) . ?
C7 C8 1.3979(16) . ?

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 112.29(11) . . ?
C1 N1 H1 125.6(13) . . ?
N2 N1 H1 121.9(13) . . ?
C2 N2 N1 103.72(11) . . ?
C1 N3 C2 107.29(10) . . ?
C1 N3 N4 121.45(11) . . ?
C2 N3 N4 130.93(11) . . ?
N3 N4 H4A 109.8(14) . . ?
N3 N4 H4B 107.9(12) . . ?
H4A N4 H4B 108.0(18) . . ?
C1 N5 H5A 116.3(14) . . ?
C1 N5 H5B 116.2(13) . . ?
H5A N5 H5B 124.5(19) . . ?
C2 N6 H6A 115.6(12) . . ?
C2 N6 H6B 116.3(14) . . ?
H6A N6 H6B 112.5(18) . . ?
C3 N7 N8 107.28(10) . . ?
C5 N8 N7 107.24(10) . . ?
N10 N9 C8 111.16(10) . . ?
N10 N9 C4 119.86(11) . . ?
C8 N9 C4 128.70(10) . . ?
C6 N10 N9 104.94(10) . . ?
C7 N11 H11A 118.5(14) . . ?
C7 N11 H11B 118.9(14) . . ?
H11A N11 H11B 121(2) . . ?
O1 N12 O2 124.90(11) . . ?
O1 N12 C3 117.68(11) . . ?
O2 N12 C3 117.42(10) . . ?
O3 N13 O4 124.37(11) . . ?
O3 N13 C5 118.45(11) . . ?
O4 N13 C5 117.18(10) . . ?
O6 N14 O5 124.66(12) . . ?
O6 N14 C6 116.96(12) . . ?
O5 N14 C6 118.37(12) . . ?
O8 N15 O7 123.83(11) . . ?
O8 N15 C8 116.96(11) . . ?
O7 N15 C8 119.21(11) . . ?
N1 C1 N5 128.46(13) . . ?
N1 C1 N3 105.83(12) . . ?
N5 C1 N3 125.69(12) . . ?
N2 C2 N6 127.39(13) . . ?
N2 C2 N3 110.84(12) . . ?
N6 C2 N3 121.63(11) . . ?
N7 C3 C4 112.31(11) . . ?
N7 C3 N12 119.59(11) . . ?
C4 C3 N12 128.10(11) . . ?
C5 C4 C3 100.93(10) . . ?
C5 C4 N9 130.28(11) . . ?
C3 C4 N9 128.79(11) . . ?
N8 C5 C4 112.24(11) . . ?
N8 C5 N13 118.97(11) . . ?
C4 C5 N13 128.79(11) . . ?
N10 C6 C7 114.25(11) . . ?
N10 C6 N14 118.61(12) . . ?
C7 C6 N14 127.14(12) . . ?
N11 C7 C8 128.97(13) . . ?
N11 C7 C6 129.92(12) . . ?
C8 C7 C6 101.10(11) . . ?
N9 C8 N15 124.36(11) . . ?
N9 C8 C7 108.55(11) . . ?
N15 C8 C7 127.03(12) . . ?

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 C2 -1.30(15) . . . . ?
C3 N7 N8 C5 -0.55(14) . . . . ?
C8 N9 N10 C6 0.40(13) . . . . ?
C4 N9 N10 C6 174.80(11) . . . . ?
N2 N1 C1 N5 -177.97(13) . . . . ?
N2 N1 C1 N3 0.56(15) . . . . ?
C2 N3 C1 N1 0.37(14) . . . . ?
N4 N3 C1 N1 174.56(12) . . . . ?
C2 N3 C1 N5 178.96(13) . . . . ?
N4 N3 C1 N5 -6.8(2) . . . . ?
N1 N2 C2 N6 -174.24(13) . . . . ?
N1 N2 C2 N3 1.49(14) . . . . ?
C1 N3 C2 N2 -1.24(15) . . . . ?
N4 N3 C2 N2 -174.68(13) . . . . ?
C1 N3 C2 N6 174.78(12) . . . . ?
N4 N3 C2 N6 1.3(2) . . . . ?
N8 N7 C3 C4 0.45(15) . . . . ?
N8 N7 C3 N12 180.00(11) . . . . ?
O1 N12 C3 N7 -18.99(18) . . . . ?
O2 N12 C3 N7 160.80(12) . . . . ?
O1 N12 C3 C4 160.49(13) . . . . ?
O2 N12 C3 C4 -19.73(19) . . . . ?
N7 C3 C4 C5 -0.15(14) . . . . ?
N12 C3 C4 C5 -179.66(12) . . . . ?
N7 C3 C4 N9 179.99(12) . . . . ?
N12 C3 C4 N9 0.5(2) . . . . ?
N10 N9 C4 C5 75.98(18) . . . . ?
C8 N9 C4 C5 -110.72(16) . . . . ?
N10 N9 C4 C3 -104.20(15) . . . . ?
C8 N9 C4 C3 69.10(19) . . . . ?
N7 N8 C5 C4 0.48(15) . . . . ?
N7 N8 C5 N13 -179.10(11) . . . . ?
C3 C4 C5 N8 -0.21(14) . . . . ?
N9 C4 C5 N8 179.65(12) . . . . ?
C3 C4 C5 N13 179.32(12) . . . . ?
N9 C4 C5 N13 -0.8(2) . . . . ?
O3 N13 C5 N8 -7.80(18) . . . . ?
O4 N13 C5 N8 171.82(12) . . . . ?
O3 N13 C5 C4 172.70(13) . . . . ?
O4 N13 C5 C4 -7.7(2) . . . . ?
N9 N10 C6 C7 -0.01(14) . . . . ?
N9 N10 C6 N14 -179.69(10) . . . . ?
O6 N14 C6 N10 174.32(11) . . . . ?
O5 N14 C6 N10 -6.22(18) . . . . ?
O6 N14 C6 C7 -5.32(19) . . . . ?
O5 N14 C6 C7 174.15(13) . . . . ?
N10 C6 C7 N11 178.45(13) . . . . ?
N14 C6 C7 N11 -1.9(2) . . . . ?
N10 C6 C7 C8 -0.36(14) . . . . ?
N14 C6 C7 C8 179.29(12) . . . . ?
N10 N9 C8 N15 -177.98(11) . . . . ?
C4 N9 C8 N15 8.2(2) . . . . ?
N10 N9 C8 C7 -0.64(14) . . . . ?
C4 N9 C8 C7 -174.42(11) . . . . ?
O8 N15 C8 N9 -174.89(12) . . . . ?
O7 N15 C8 N9 5.68(18) . . . . ?
O8 N15 C8 C7 8.27(19) . . . . ?
O7 N15 C8 C7 -171.17(12) . . . . ?
N11 C7 C8 N9 -178.25(13) . . . . ?
C6 C7 C8 N9 0.57(13) . . . . ?
N11 C7 C8 N15 -1.0(2) . . . . ?
C6 C7 C8 N15 177.82(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052


_database_code_depnum_ccdc_archive 'CCDC 1014095'
#######################################################################
#
#                 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_bo2527

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H4 N10 O8'
_chemical_formula_weight         344.19

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'
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

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                   10.6525(18)
_cell_length_b                   10.1569(17)
_cell_length_c                   11.3404(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.259(2)
_cell_angle_gamma                90.00
_cell_volume                     1219.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3602
_cell_measurement_theta_min      2.699
_cell_measurement_theta_max      29.131

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9231
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10561
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         29.12
_reflns_number_total             3264
_reflns_number_gt                2619
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0695P)²+0.9690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3264
_refine_ls_number_parameters     231
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.22915(15) 0.32475(18) 0.41143(15) 0.0477(4) Uani 1 1 d . . .
O2 O 0.42753(16) 0.38324(17) 0.43070(14) 0.0457(4) Uani 1 1 d . . .
O3 O 0.17655(17) 0.05174(18) 0.82340(16) 0.0503(5) Uani 1 1 d . . .
O4 O 0.36850(18) 0.01340(18) 0.89942(15) 0.0495(4) Uani 1 1 d . . .
O5 O 0.52402(19) 0.0978(2) 0.42634(16) 0.0597(5) Uani 1 1 d . . .
O6 O 0.7051(2) 0.12927(19) 0.36047(17) 0.0591(6) Uani 1 1 d . . .
O7 O 0.54510(16) 0.43670(17) 0.81521(15) 0.0452(4) Uani 1 1 d . . .
O8 O 0.74439(19) 0.4807(2) 0.84768(17) 0.0603(5) Uani 1 1 d . . .
N1 N 0.46876(15) 0.23834(16) 0.63909(14) 0.0277(3) Uani 1 1 d . . .
N2 N 0.45708(16) 0.16732(16) 0.73678(14) 0.0299(4) Uani 1 1 d . . .
N3 N 0.13723(18) 0.1821(3) 0.5990(2) 0.0483(5) Uani 1 1 d D . .
N4 N 0.78152(18) 0.27737(18) 0.54588(17) 0.0386(4) Uani 1 1 d . . .
N5 N 0.78636(16) 0.35066(17) 0.64194(16) 0.0337(4) Uani 1 1 d . . .
N6 N 0.9029(2) 0.4035(2) 0.6823(2) 0.0532(6) Uani 1 1 d D . .
N7 N 0.33661(17) 0.32569(18) 0.46558(16) 0.0355(4) Uani 1 1 d . . .
N8 N 0.29139(18) 0.06294(18) 0.82593(17) 0.0380(4) Uani 1 1 d . . .
N9 N 0.6281(2) 0.14719(19) 0.43207(17) 0.0418(5) Uani 1 1 d . . .
N10 N 0.65235(17) 0.42943(18) 0.79091(16) 0.0355(4) Uani 1 1 d . . .
C1 C 0.35321(18) 0.2552(2) 0.57222(18) 0.0311(4) Uani 1 1 d . . .
C2 C 0.26104(19) 0.1924(2) 0.63133(19) 0.0344(4) Uani 1 1 d . . .
C3 C 0.33462(19) 0.1419(2) 0.73206(18) 0.0317(4) Uani 1 1 d . . .
C4 C 0.6649(2) 0.23217(19) 0.53119(18) 0.0319(4) Uani 1 1 d . . .
C5 C 0.59071(18) 0.27525(18) 0.61786(16) 0.0275(4) Uani 1 1 d . . .
C6 C 0.67395(18) 0.35363(19) 0.68891(17) 0.0296(4) Uani 1 1 d . . .
H3A H 0.109(2) 0.218(2) 0.5335(14) 0.043(7) Uiso 1 1 d D . .
H3B H 0.093(3) 0.136(3) 0.641(2) 0.095 Uiso 1 1 d D . .
H6A H 0.880(4) 0.449(3) 0.742(2) 0.098(14) Uiso 1 1 d D . .
H6B H 0.930(3) 0.441(3) 0.6205(19) 0.094 Uiso 1 1 d 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 N7 1.239(2) . ?
O2 N7 1.233(2) . ?
O3 N8 1.226(2) . ?
O4 N8 1.214(3) . ?
O5 N9 1.212(3) . ?
O6 N9 1.229(2) . ?
O7 N10 1.206(2) . ?
O8 N10 1.229(2) . ?
N1 N2 1.339(2) . ?
N1 C1 1.384(2) . ?
N1 C5 1.398(2) . ?
N2 C3 1.325(3) . ?
N3 C2 1.334(3) . ?
N3 H3A 0.850(9) . ?
N3 H3B 0.850(9) . ?
N4 N5 1.316(3) . ?
N4 C4 1.318(3) . ?
N5 C6 1.363(3) . ?
N5 N6 1.384(3) . ?
N6 H6A 0.872(10) . ?
N6 H6B 0.874(10) . ?
N7 C1 1.400(3) . ?
N8 C3 1.448(3) . ?
N9 C4 1.437(3) . ?
N10 C6 1.429(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.410(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.383(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 N1 C1 111.26(16) . . ?
N2 N1 C5 117.32(15) . . ?
C1 N1 C5 131.29(16) . . ?
C3 N2 N1 104.56(16) . . ?
C2 N3 H3A 116.7(16) . . ?
C2 N3 H3B 119.0(19) . . ?
H3A N3 H3B 124.0(16) . . ?
N5 N4 C4 104.66(17) . . ?
N4 N5 C6 112.29(17) . . ?
N4 N5 N6 116.49(19) . . ?
C6 N5 N6 131.1(2) . . ?
N5 N6 H6A 98(3) . . ?
N5 N6 H6B 106(3) . . ?
H6A N6 H6B 122.5(19) . . ?
O2 N7 O1 124.09(19) . . ?
O2 N7 C1 119.34(17) . . ?
O1 N7 C1 116.57(19) . . ?
O4 N8 O3 125.2(2) . . ?
O4 N8 C3 119.27(18) . . ?
O3 N8 C3 115.52(19) . . ?
O5 N9 O6 125.1(2) . . ?
O5 N9 C4 117.41(19) . . ?
O6 N9 C4 117.4(2) . . ?
O7 N10 O8 125.17(19) . . ?
O7 N10 C6 117.25(17) . . ?
O8 N10 C6 117.58(18) . . ?
N1 C1 N7 123.90(18) . . ?
N1 C1 C2 108.00(18) . . ?
N7 C1 C2 128.09(19) . . ?
N3 C2 C1 128.9(2) . . ?
N3 C2 C3 129.8(2) . . ?
C1 C2 C3 101.34(17) . . ?
N2 C3 C2 114.83(18) . . ?
N2 C3 N8 117.96(19) . . ?
C2 C3 N8 127.17(19) . . ?
N4 C4 C5 113.57(19) . . ?
N4 C4 N9 118.75(19) . . ?
C5 C4 N9 127.68(19) . . ?
C6 C5 C4 102.36(17) . . ?
C6 C5 N1 127.06(18) . . ?
C4 C5 N1 130.16(18) . . ?
N5 C6 C5 107.12(17) . . ?
N5 C6 N10 123.65(18) . . ?
C5 C6 N10 129.21(18) . . ?

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 -1.1(2) . . . . ?
C5 N1 N2 C3 -177.43(16) . . . . ?
C4 N4 N5 C6 -0.3(2) . . . . ?
C4 N4 N5 N6 175.68(19) . . . . ?
N2 N1 C1 N7 179.81(18) . . . . ?
C5 N1 C1 N7 -4.5(3) . . . . ?
N2 N1 C1 C2 0.7(2) . . . . ?
C5 N1 C1 C2 176.45(19) . . . . ?
O2 N7 C1 N1 -4.3(3) . . . . ?
O1 N7 C1 N1 175.15(18) . . . . ?
O2 N7 C1 C2 174.6(2) . . . . ?
O1 N7 C1 C2 -6.0(3) . . . . ?
N1 C1 C2 N3 -179.2(2) . . . . ?
N7 C1 C2 N3 1.8(4) . . . . ?
N1 C1 C2 C3 -0.1(2) . . . . ?
N7 C1 C2 C3 -179.1(2) . . . . ?
N1 N2 C3 C2 1.0(2) . . . . ?
N1 N2 C3 N8 178.77(16) . . . . ?
N3 C2 C3 N2 178.5(2) . . . . ?
C1 C2 C3 N2 -0.6(2) . . . . ?
N3 C2 C3 N8 1.0(4) . . . . ?
C1 C2 C3 N8 -178.08(19) . . . . ?
O4 N8 C3 N2 -6.3(3) . . . . ?
O3 N8 C3 N2 173.88(18) . . . . ?
O4 N8 C3 C2 171.1(2) . . . . ?
O3 N8 C3 C2 -8.7(3) . . . . ?
N5 N4 C4 C5 0.0(2) . . . . ?
N5 N4 C4 N9 180.00(18) . . . . ?
O5 N9 C4 N4 173.7(2) . . . . ?
O6 N9 C4 N4 -5.6(3) . . . . ?
O5 N9 C4 C5 -6.3(3) . . . . ?
O6 N9 C4 C5 174.4(2) . . . . ?
N4 C4 C5 C6 0.3(2) . . . . ?
N9 C4 C5 C6 -179.7(2) . . . . ?
N4 C4 C5 N1 -172.59(19) . . . . ?
N9 C4 C5 N1 7.4(3) . . . . ?
N2 N1 C5 C6 -61.6(3) . . . . ?
C1 N1 C5 C6 122.9(2) . . . . ?
N2 N1 C5 C4 109.6(2) . . . . ?
C1 N1 C5 C4 -65.9(3) . . . . ?
N4 N5 C6 C5 0.5(2) . . . . ?
N6 N5 C6 C5 -174.7(2) . . . . ?
N4 N5 C6 N10 -177.80(18) . . . . ?
N6 N5 C6 N10 7.0(3) . . . . ?
C4 C5 C6 N5 -0.4(2) . . . . ?
N1 C5 C6 N5 172.75(18) . . . . ?
C4 C5 C6 N10 177.7(2) . . . . ?
N1 C5 C6 N10 -9.1(3) . . . . ?
O7 N10 C6 N5 171.12(19) . . . . ?
O8 N10 C6 N5 -9.7(3) . . . . ?
O7 N10 C6 C5 -6.8(3) . . . . ?
O8 N10 C6 C5 172.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.066

_database_code_depnum_ccdc_archive 'CCDC 1014096'
#######################################################################
#
#                 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_bo2526

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H10 N14 O8'
_chemical_formula_weight         418.29

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   C2/c

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                   30.534(7)
_cell_length_b                   9.1162(19)
_cell_length_c                   12.213(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.504(3)
_cell_angle_gamma                90.00
_cell_volume                     3242.1(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5501
_cell_measurement_theta_min      2.341
_cell_measurement_theta_max      29.123

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9314
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14056
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         29.14
_reflns_number_total             4312
_reflns_number_gt                3544
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0839P)²+0.2160P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4312
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28775(4) 0.55099(13) 0.49556(10) 0.0287(3) Uani 1 1 d . . .
O2 O 0.22343(4) 0.65415(13) 0.39841(11) 0.0298(3) Uani 1 1 d . . .
O3 O 0.23987(4) 0.11013(13) 0.73568(10) 0.0284(3) Uani 1 1 d . . .
O4 O 0.16515(4) 0.12101(13) 0.69355(11) 0.0318(3) Uani 1 1 d . . .
O5 O 0.12450(4) 0.12167(13) 0.40617(11) 0.0320(3) Uani 1 1 d . . .
O6 O 0.05064(4) 0.09391(15) 0.35914(12) 0.0385(3) Uani 1 1 d . . .
O7 O 0.15368(5) 0.58676(17) 0.71762(12) 0.0441(4) Uani 1 1 d . . .
O8 O 0.08983(5) 0.59531(15) 0.76194(11) 0.0395(3) Uani 1 1 d . . .
N1 N 0.17655(4) 0.47826(14) 0.49939(11) 0.0212(3) Uani 1 1 d . . .
N2 N 0.16503(4) 0.36972(14) 0.55823(11) 0.0204(3) Uani 1 1 d . . .
N3 N 0.28607(4) 0.31552(16) 0.64329(12) 0.0235(3) Uani 1 1 d . . .
N4 N 0.04510(4) 0.28466(16) 0.52123(12) 0.0260(3) Uani 1 1 d . . .
N5 N 0.05234(5) 0.39074(15) 0.60164(12) 0.0264(3) Uani 1 1 d . . .
N6 N 0.24553(4) 0.56528(14) 0.46907(11) 0.0223(3) Uani 1 1 d . . .
N7 N 0.20230(4) 0.16810(15) 0.68746(11) 0.0228(3) Uani 1 1 d . . .
N8 N 0.08649(5) 0.15303(15) 0.41511(12) 0.0251(3) Uani 1 1 d . . .
N9 N 0.11422(5) 0.54640(16) 0.70688(12) 0.0282(3) Uani 1 1 d . . .
N10 N 0.37682(5) 0.74457(19) 0.63461(14) 0.0314(3) Uani 1 1 d . . .
N11 N 0.39218(5) 0.70323(17) 0.54145(13) 0.0286(3) Uani 1 1 d . . .
N12 N 0.45758(5) 0.83880(18) 0.61929(14) 0.0332(4) Uani 1 1 d . . .
N13 N 0.45082(5) 0.69522(19) 0.45992(13) 0.0340(4) Uani 1 1 d . . .
N14 N 0.42624(7) 0.5844(2) 0.38715(15) 0.0407(4) Uani 1 1 d . . .
C1 C 0.22204(5) 0.46917(16) 0.52467(13) 0.0197(3) Uani 1 1 d . . .
C2 C 0.24202(5) 0.35580(16) 0.60230(13) 0.0194(3) Uani 1 1 d . . .
C3 C 0.20344(5) 0.29299(17) 0.62204(12) 0.0195(3) Uani 1 1 d . . .
C4 C 0.08439(5) 0.26395(17) 0.49594(13) 0.0223(3) Uani 1 1 d . . .
C5 C 0.11899(5) 0.35673(17) 0.55937(13) 0.0206(3) Uani 1 1 d . . .
C6 C 0.09609(5) 0.43369(17) 0.62378(13) 0.0227(3) Uani 1 1 d . . .
C7 C 0.43371(5) 0.74489(19) 0.54160(14) 0.0263(3) Uani 1 1 d . . .
H3A H 0.3075(8) 0.371(2) 0.6280(18) 0.036(6) Uiso 1 1 d . . .
H3B H 0.2930(7) 0.242(2) 0.6952(18) 0.036(5) Uiso 1 1 d . . .
H10A H 0.3723(8) 0.662(2) 0.6719(19) 0.040(6) Uiso 1 1 d . . .
H10B H 0.3492(9) 0.789(3) 0.605(2) 0.060(7) Uiso 1 1 d . . .
H11 H 0.3781(8) 0.639(2) 0.4908(19) 0.037(6) Uiso 1 1 d . . .
H12A H 0.4851(8) 0.868(2) 0.6181(18) 0.037(6) Uiso 1 1 d . . .
H12B H 0.4455(8) 0.873(3) 0.665(2) 0.045(6) Uiso 1 1 d . . .
H13 H 0.4793(8) 0.724(2) 0.4583(19) 0.047(6) Uiso 1 1 d . . .
H14A H 0.4465(10) 0.506(3) 0.390(2) 0.069(8) Uiso 1 1 d . . .
H14B H 0.4199(11) 0.616(3) 0.315(3) 0.082(10) 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 N6 1.2380(16) . ?
O2 N6 1.2273(17) . ?
O3 N7 1.2392(17) . ?
O4 N7 1.2358(17) . ?
O5 N8 1.2316(17) . ?
O6 N8 1.2271(18) . ?
O7 N9 1.2284(19) . ?
O8 N9 1.2277(18) . ?
N1 N2 1.3309(18) . ?
N1 C1 1.3316(18) . ?
N2 C3 1.3864(18) . ?
N2 C5 1.4151(19) . ?
N3 C2 1.3377(19) . ?
N3 H3A 0.89(2) . ?
N3 H3B 0.90(2) . ?
N4 C4 1.3391(18) . ?
N4 N5 1.3482(19) . ?
N5 C6 1.339(2) . ?
N6 C1 1.4270(19) . ?
N7 C3 1.397(2) . ?
N8 C4 1.428(2) . ?
N9 C6 1.433(2) . ?
N10 N11 1.406(2) . ?
N10 H10A 0.91(2) . ?
N10 H10B 0.91(3) . ?
N11 C7 1.323(2) . ?
N11 H11 0.86(2) . ?
N12 C7 1.322(2) . ?
N12 H12A 0.89(2) . ?
N12 H12B 0.82(2) . ?
N13 C7 1.337(2) . ?
N13 N14 1.405(2) . ?
N13 H13 0.91(2) . ?
N14 H14A 0.94(3) . ?
N14 H14B 0.90(3) . ?
C1 C2 1.411(2) . ?
C2 C3 1.395(2) . ?
C4 C5 1.392(2) . ?
C5 C6 1.390(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
N2 N1 C1 104.78(12) . . ?
N1 N2 C3 111.24(12) . . ?
N1 N2 C5 119.49(12) . . ?
C3 N2 C5 128.84(13) . . ?
C2 N3 H3A 119.0(14) . . ?
C2 N3 H3B 117.6(13) . . ?
H3A N3 H3B 122.6(19) . . ?
C4 N4 N5 107.89(13) . . ?
C6 N5 N4 106.97(13) . . ?
O2 N6 O1 124.22(13) . . ?
O2 N6 C1 119.40(13) . . ?
O1 N6 C1 116.37(13) . . ?
O4 N7 O3 123.95(14) . . ?
O4 N7 C3 119.91(13) . . ?
O3 N7 C3 116.14(13) . . ?
O6 N8 O5 123.72(15) . . ?
O6 N8 C4 118.57(13) . . ?
O5 N8 C4 117.71(13) . . ?
O8 N9 O7 124.74(15) . . ?
O8 N9 C6 118.65(14) . . ?
O7 N9 C6 116.61(14) . . ?
N11 N10 H10A 108.8(13) . . ?
N11 N10 H10B 107.3(16) . . ?
H10A N10 H10B 108(2) . . ?
C7 N11 N10 118.33(15) . . ?
C7 N11 H11 117.6(15) . . ?
N10 N11 H11 123.0(15) . . ?
C7 N12 H12A 120.3(14) . . ?
C7 N12 H12B 118.3(17) . . ?
H12A N12 H12B 121(2) . . ?
C7 N13 N14 117.49(15) . . ?
C7 N13 H13 120.6(14) . . ?
N14 N13 H13 121.4(14) . . ?
N13 N14 H14A 107.7(17) . . ?
N13 N14 H14B 108(2) . . ?
H14A N14 H14B 103(3) . . ?
N1 C1 C2 114.30(13) . . ?
N1 C1 N6 119.34(13) . . ?
C2 C1 N6 126.27(13) . . ?
N3 C2 C3 128.99(15) . . ?
N3 C2 C1 129.45(14) . . ?
C3 C2 C1 101.52(12) . . ?
N2 C3 C2 108.15(13) . . ?
N2 C3 N7 124.76(13) . . ?
C2 C3 N7 126.94(13) . . ?
N4 C4 C5 111.61(14) . . ?
N4 C4 N8 119.26(14) . . ?
C5 C4 N8 129.09(14) . . ?
C6 C5 C4 101.25(13) . . ?
C6 C5 N2 129.33(14) . . ?
C4 C5 N2 129.42(14) . . ?
N5 C6 C5 112.28(14) . . ?
N5 C6 N9 120.13(14) . . ?
C5 C6 N9 127.59(14) . . ?
N12 C7 N11 120.52(16) . . ?
N12 C7 N13 120.02(15) . . ?
N11 C7 N13 119.42(16) . . ?

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 0.76(16) . . . . ?
C1 N1 N2 C5 173.92(13) . . . . ?
C4 N4 N5 C6 0.30(18) . . . . ?
N2 N1 C1 C2 -0.90(17) . . . . ?
N2 N1 C1 N6 175.90(13) . . . . ?
O2 N6 C1 N1 -0.4(2) . . . . ?
O1 N6 C1 N1 -179.55(13) . . . . ?
O2 N6 C1 C2 175.98(14) . . . . ?
O1 N6 C1 C2 -3.2(2) . . . . ?
N1 C1 C2 N3 178.62(15) . . . . ?
N6 C1 C2 N3 2.1(3) . . . . ?
N1 C1 C2 C3 0.67(17) . . . . ?
N6 C1 C2 C3 -175.88(14) . . . . ?
N1 N2 C3 C2 -0.38(17) . . . . ?
C5 N2 C3 C2 -172.73(14) . . . . ?
N1 N2 C3 N7 -176.16(14) . . . . ?
C5 N2 C3 N7 11.5(2) . . . . ?
N3 C2 C3 N2 -178.13(15) . . . . ?
C1 C2 C3 N2 -0.16(16) . . . . ?
N3 C2 C3 N7 -2.5(3) . . . . ?
C1 C2 C3 N7 175.51(14) . . . . ?
O4 N7 C3 N2 -1.9(2) . . . . ?
O3 N7 C3 N2 177.36(14) . . . . ?
O4 N7 C3 C2 -176.90(15) . . . . ?
O3 N7 C3 C2 2.4(2) . . . . ?
N5 N4 C4 C5 -0.09(19) . . . . ?
N5 N4 C4 N8 177.93(13) . . . . ?
O6 N8 C4 N4 10.1(2) . . . . ?
O5 N8 C4 N4 -169.49(14) . . . . ?
O6 N8 C4 C5 -172.26(16) . . . . ?
O5 N8 C4 C5 8.1(2) . . . . ?
N4 C4 C5 C6 -0.14(18) . . . . ?
N8 C4 C5 C6 -177.92(16) . . . . ?
N4 C4 C5 N2 -179.88(15) . . . . ?
N8 C4 C5 N2 2.3(3) . . . . ?
N1 N2 C5 C6 -79.6(2) . . . . ?
C3 N2 C5 C6 92.2(2) . . . . ?
N1 N2 C5 C4 100.11(19) . . . . ?
C3 N2 C5 C4 -88.1(2) . . . . ?
N4 N5 C6 C5 -0.40(18) . . . . ?
N4 N5 C6 N9 -179.88(14) . . . . ?
C4 C5 C6 N5 0.33(18) . . . . ?
N2 C5 C6 N5 -179.92(15) . . . . ?
C4 C5 C6 N9 179.76(15) . . . . ?
N2 C5 C6 N9 -0.5(3) . . . . ?
O8 N9 C6 N5 4.6(2) . . . . ?
O7 N9 C6 N5 -175.56(15) . . . . ?
O8 N9 C6 C5 -174.79(16) . . . . ?
O7 N9 C6 C5 5.1(2) . . . . ?
N10 N11 C7 N12 -8.8(2) . . . . ?
N10 N11 C7 N13 173.55(16) . . . . ?
N14 N13 C7 N12 173.49(17) . . . . ?
N14 N13 C7 N11 -8.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.053

_database_code_depnum_ccdc_archive 'CCDC 1014097'
