# 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_added_by_encifer
_audit_creation_method           SHELXL-97




_chemical_name_systematic        
; 

 ? 

;




_chemical_name_common            ?




_chemical_melting_point          ?




_chemical_formula_moiety         ?




_chemical_formula_sum            
'C4 H12 Cl2 N10 O2'




_chemical_formula_weight         303.14






loop_



_atom_type_symbol



_atom_type_description



_atom_type_scat_dispersion_real



_atom_type_scat_dispersion_imag




_atom_type_scat_source





C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Triclinic




_symmetry_space_group_name_H-M   P-1






loop_



_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'






_cell_length_a                   5.186(2)




_cell_length_b                   7.387(3)




_cell_length_c                   8.416(4)




_cell_angle_alpha                109.629(4)




_cell_angle_beta                 96.520(6)




_cell_angle_gamma                94.311(7)




_cell_volume                     299.4(2)




_cell_formula_units_Z            1




_cell_measurement_temperature    93(2)




_cell_measurement_reflns_used    1311




_cell_measurement_theta_min      2.60




_cell_measurement_theta_max      32.54






_exptl_crystal_description       Prism




_exptl_crystal_colour            Colorless




_exptl_crystal_size_max          0.47




_exptl_crystal_size_mid          0.27




_exptl_crystal_size_min          0.25




_exptl_crystal_density_meas      ?




_exptl_crystal_density_diffrn    1.681




_exptl_crystal_density_method    'not measured'




_exptl_crystal_F_000             156




_exptl_absorpt_coefficient_mu    0.558




_exptl_absorpt_correction_type   Multi-scans




_exptl_absorpt_correction_T_min  0.7807




_exptl_absorpt_correction_T_max  0.8731




_exptl_absorpt_process_details   ?






_exptl_special_details           
; 

 ? 

;






_diffrn_ambient_temperature      93(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            3948




_diffrn_reflns_av_R_equivalents  0.0271




_diffrn_reflns_av_sigmaI/netI    0.0456




_diffrn_reflns_limit_h_min       -7




_diffrn_reflns_limit_h_max       7




_diffrn_reflns_limit_k_min       -11




_diffrn_reflns_limit_k_max       11




_diffrn_reflns_limit_l_min       -12




_diffrn_reflns_limit_l_max       11




_diffrn_reflns_theta_min         2.60




_diffrn_reflns_theta_max         32.57




_reflns_number_total             2108




_reflns_number_gt                1767




_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)+(0.0183P)²+0.1560P] 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         2108




_refine_ls_number_parameters     102




_refine_ls_number_restraints     0




_refine_ls_R_factor_all          0.0402




_refine_ls_R_factor_gt           0.0323




_refine_ls_wR_factor_ref         0.0710




_refine_ls_wR_factor_gt          0.0680




_refine_ls_goodness_of_fit_ref   1.002




_refine_ls_restrained_S_all      1.002




_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































































Cl1 Cl 0.89754(6) 1.07631(4) 0.79915(4) 0.01351(8) Uani 1 1 d . . .
O1 O 0.3737(2) 0.82464(14) 0.79087(12) 0.01556(19) Uani 1 1 d . . .
N1 N 0.2982(2) 0.62851(15) 0.44541(13) 0.0123(2) Uani 1 1 d . . .
N2 N 0.1101(2) 0.47941(15) 0.33920(13) 0.0141(2) Uani 1 1 d . . .
N3 N 0.4078(2) 0.54939(14) 0.19538(12) 0.01057(19) Uani 1 1 d . . .
N4 N 0.5528(2) 0.55846(14) 0.07101(12) 0.01113(19) Uani 1 1 d . . .
N5 N 0.6845(2) 0.80487(16) 0.41550(14) 0.0141(2) Uani 1 1 d . . .
C1 C 0.4794(2) 0.67307(17) 0.35993(14) 0.0110(2) Uani 1 1 d . . .
C2 C 0.1790(2) 0.43404(17) 0.18926(15) 0.0133(2) Uani 1 1 d . . .
H2 H 0.0871 0.3364 0.0895 0.016 Uiso 1 1 calc R . .
H1 H 0.293(4) 0.681(3) 0.554(3) 0.032(5) Uiso 1 1 d . . .
H1A H 0.249(4) 0.892(3) 0.819(3) 0.040(6) Uiso 1 1 d . . .
H1B H 0.509(4) 0.906(3) 0.821(3) 0.035(5) Uiso 1 1 d . . .
H5A H 0.784(4) 0.818(3) 0.345(3) 0.030(5) Uiso 1 1 d . . .
H5B H 0.723(4) 0.868(3) 0.521(2) 0.027(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 H1A 0.85(2) . ?
O1 H1B 0.84(2) . ?
N1 C1 1.3324(17) . ?
N1 N2 1.3936(15) . ?
N1 H1 0.87(2) . ?
N2 C2 1.2917(17) . ?
N3 C1 1.3684(16) . ?
N3 N4 1.3722(15) . ?
N3 C2 1.3934(16) . ?
N4 N4 1.249(2) 2_665 ?
N5 C1 1.3126(17) . ?
N5 H5A 0.85(2) . ?
N5 H5B 0.847(19) . ?
C2 H2 0.9500 . ?






loop_



_geom_angle_atom_site_label_1



_geom_angle_atom_site_label_2



_geom_angle_atom_site_label_3



_geom_angle



_geom_angle_site_symmetry_1



_geom_angle_site_symmetry_3



_geom_angle_publ_flag










































H1A O1 H1B 104.4(19) . . ?
C1 N1 N2 111.67(10) . . ?
C1 N1 H1 126.6(13) . . ?
N2 N1 H1 121.7(12) . . ?
C2 N2 N1 105.56(11) . . ?
C1 N3 N4 120.28(10) . . ?
C1 N3 C2 107.84(10) . . ?
N4 N3 C2 131.86(10) . . ?
N4 N4 N3 110.26(13) 2_665 . ?
C1 N5 H5A 119.2(13) . . ?
C1 N5 H5B 119.4(12) . . ?
H5A N5 H5B 121.2(18) . . ?
N5 C1 N1 129.35(12) . . ?
N5 C1 N3 125.71(11) . . ?
N1 C1 N3 104.94(11) . . ?
N2 C2 N3 109.98(11) . . ?
N2 C2 H2 125.0 . . ?
N3 C2 H2 125.0 . . ?






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 0.08(14) . . . . ?
C1 N3 N4 N4 -176.34(12) . . . 2_665 ?
C2 N3 N4 N4 1.7(2) . . . 2_665 ?
N2 N1 C1 N5 179.66(12) . . . . ?
N2 N1 C1 N3 -0.37(13) . . . . ?
N4 N3 C1 N5 -1.03(18) . . . . ?
C2 N3 C1 N5 -179.52(12) . . . . ?
N4 N3 C1 N1 179.00(10) . . . . ?
C2 N3 C1 N1 0.51(13) . . . . ?
N1 N2 C2 N3 0.25(14) . . . . ?
C1 N3 C2 N2 -0.49(14) . . . . ?
N4 N3 C2 N2 -178.74(11) . . . . ?






_diffrn_measured_fraction_theta_max 0.969




_diffrn_reflns_theta_full        32.57

_diffrn_measured_fraction_theta_full 0.969




_refine_diff_density_max         0.452




_refine_diff_density_min         -0.285




_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 963404'
#######################################################################
#
#                 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_added_by_encifer


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H8 N12 O6'
_chemical_formula_weight         320.22

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

_symmetry_cell_setting           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                   7.2555(15)
_cell_length_b                   8.8270(18)
_cell_length_c                   9.796(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.70(3)
_cell_angle_gamma                90.00
_cell_volume                     604.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1759
_cell_measurement_theta_min      3.1244
_cell_measurement_theta_max      27.8465

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5973
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.91
_reflns_number_total             1426
_reflns_number_gt                1081
_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)+(0.0923P)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       0.15(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1426
_refine_ls_number_parameters     110
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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
N1 N 0.1710(2) 0.89661(15) 0.57327(17) 0.0459(4) Uani 1 1 d . . .
N2 N 0.3477(2) 0.82798(15) 0.62882(16) 0.0404(4) Uani 1 1 d D . .
H2 H 0.4522(18) 0.8855(19) 0.6557(18) 0.049 Uiso 1 1 d D . .
N3 N 0.47069(18) 0.57570(16) 0.65764(16) 0.0421(4) Uani 1 1 d D . .
H3A H 0.442(2) 0.4805(12) 0.6420(18) 0.051 Uiso 1 1 d D . .
H3B H 0.5883(16) 0.6044(18) 0.697(2) 0.051 Uiso 1 1 d D . .
N4 N 0.14770(16) 0.64881(13) 0.55867(14) 0.0311(4) Uani 1 1 d . . .
N5 N 0.08644(16) 0.50220(13) 0.53125(13) 0.0300(4) Uani 1 1 d . . .
C1 C 0.0523(2) 0.78763(18) 0.53093(19) 0.0389(4) Uani 1 1 d . . .
H1 H -0.0780 0.7993 0.4881 0.047 Uiso 1 1 calc R . .
C2 C 0.3374(2) 0.67805(17) 0.61987(16) 0.0325(4) Uani 1 1 d . . .
O1 O 0.79339(16) 0.78881(14) 0.80368(15) 0.0524(4) Uani 1 1 d . . .
O2 O 0.89250(18) 0.56589(13) 0.77762(16) 0.0582(4) Uani 1 1 d . . .
O3 O 1.09550(17) 0.74194(17) 0.87129(17) 0.0588(5) Uani 1 1 d . . .
N6 N 0.92839(17) 0.69847(14) 0.81861(14) 0.0344(4) 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
N1 C1 1.283(2) . ?
N1 N2 1.389(2) . ?
N2 C2 1.327(2) . ?
N2 H2 0.891(9) . ?
N3 C2 1.302(2) . ?
N3 H3A 0.870(9) . ?
N3 H3B 0.873(9) . ?
N4 C2 1.369(2) . ?
N4 N5 1.3711(16) . ?
N4 C1 1.3975(18) . ?
N5 N5 1.239(2) 3_566 ?
C1 H1 0.9300 . ?
O1 N6 1.2407(16) . ?
O2 N6 1.2418(16) . ?
O3 N6 1.2429(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 105.52(13) . . ?
C2 N2 N1 112.31(12) . . ?
C2 N2 H2 128.0(12) . . ?
N1 N2 H2 119.3(12) . . ?
C2 N3 H3A 119.7(11) . . ?
C2 N3 H3B 119.1(12) . . ?
H3A N3 H3B 121.2(14) . . ?
C2 N4 N5 119.87(12) . . ?
C2 N4 C1 107.84(12) . . ?
N5 N4 C1 132.24(13) . . ?
N5 N5 N4 110.96(14) 3_566 . ?
N1 C1 N4 109.90(14) . . ?
N1 C1 H1 125.1 . . ?
N4 C1 H1 125.1 . . ?
N3 C2 N2 130.46(14) . . ?
N3 C2 N4 125.12(14) . . ?
N2 C2 N4 104.42(13) . . ?
O1 N6 O2 118.54(13) . . ?
O1 N6 O3 120.06(13) . . ?
O2 N6 O3 121.39(13) . . ?

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 0.3(2) . . . . ?
C2 N4 N5 N5 -176.19(15) . . . 3_566 ?
C1 N4 N5 N5 0.9(3) . . . 3_566 ?
N2 N1 C1 N4 0.42(19) . . . . ?
C2 N4 C1 N1 -1.02(19) . . . . ?
N5 N4 C1 N1 -178.32(16) . . . . ?
N1 N2 C2 N3 178.73(17) . . . . ?
N1 N2 C2 N4 -0.94(18) . . . . ?
N5 N4 C2 N3 -0.8(2) . . . . ?
C1 N4 C2 N3 -178.54(15) . . . . ?
N5 N4 C2 N2 178.85(13) . . . . ?
C1 N4 C2 N2 1.15(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.056


_database_code_depnum_ccdc_archive 'CCDC 976507'
#######################################################################
#
#                 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_added_by_encifer



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 N8 O2'
_chemical_formula_weight         224.20

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                   5.854(4)
_cell_length_b                   8.130(5)
_cell_length_c                   10.650(7)
_cell_angle_alpha                109.96(3)
_cell_angle_beta                 96.98(4)
_cell_angle_gamma                100.02(3)
_cell_volume                     460.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1257
_cell_measurement_theta_min      3.604
_cell_measurement_theta_max      27.523

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232
_exptl_absorpt_coefficient_mu    0.129
_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            4614
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0892
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2073
_reflns_number_gt                859
_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)+(0.0116P)²+0.0486P] 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         2073
_refine_ls_number_parameters     295
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      0.998
_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
N1 N 0.5506(8) 0.6176(14) 0.2782(6) 0.0241(14) Uani 0.599(5) 1 d PD A 1
N2 N 0.6152(13) 0.6979(11) 0.1892(6) 0.0248(14) Uani 0.599(5) 1 d PD A 1
N3 N 0.2473(16) 0.5452(15) 0.1192(10) 0.0144(16) Uani 0.599(5) 1 d PD A 1
N4 N 0.0170(6) 0.4758(5) 0.0502(4) 0.0209(9) Uani 0.599(5) 1 d PD . 1
C1 C 0.3221(7) 0.5248(6) 0.2410(4) 0.0188(10) Uani 0.599(5) 1 d PD A 1
C2 C 0.4279(8) 0.6589(6) 0.0961(4) 0.0193(10) Uani 0.599(5) 1 d PD A 1
H2 H 0.4167 0.7018 0.0235 0.023 Uiso 0.599(5) 1 calc PR A 1
C3 C 0.7230(15) 0.623(2) 0.3901(9) 0.042(3) Uani 0.599(5) 1 d PD A 1
H3A H 0.6418 0.6025 0.4606 0.050 Uiso 0.599(5) 1 calc PR A 1
H3B H 0.8342 0.7408 0.4287 0.050 Uiso 0.599(5) 1 calc PR A 1
H3C H 0.8098 0.5290 0.3569 0.050 Uiso 0.599(5) 1 calc PR A 1
N5 N 0.5061(7) 0.9066(9) 0.6962(4) 0.0188(12) Uani 0.621(5) 1 d PD B 1
N6 N 0.7006(9) 1.0079(10) 0.6744(7) 0.0285(14) Uani 0.621(5) 1 d PD B 1
N7 N 0.7837(14) 0.9699(14) 0.8666(9) 0.0197(14) Uani 0.621(5) 1 d PDU B 1
N8 N 0.8945(6) 0.9548(5) 0.9834(3) 0.0226(9) Uani 0.621(5) 1 d PD . 1
C4 C 0.5459(7) 0.8731(5) 0.8123(4) 0.0175(10) Uani 0.621(5) 1 d PD B 1
C5 C 0.8668(7) 1.0431(6) 0.7809(4) 0.0214(10) Uani 0.621(5) 1 d PD B 1
H5 H 1.0237 1.1109 0.7953 0.026 Uiso 0.621(5) 1 calc PR B 1
C6 C 0.2837(11) 0.8460(19) 0.6008(9) 0.037(3) Uani 0.621(5) 1 d PD B 1
H6A H 0.1593 0.7963 0.6404 0.044 Uiso 0.621(5) 1 calc PR B 1
H6B H 0.2973 0.7529 0.5165 0.044 Uiso 0.621(5) 1 calc PR B 1
H6C H 0.2435 0.9477 0.5807 0.044 Uiso 0.621(5) 1 calc PR B 1
O1 O 0.2143(8) 0.4361(6) 0.2966(5) 0.0259(11) Uani 0.599(5) 1 d P A 1
O2 O 0.4146(8) 0.7893(9) 0.8596(5) 0.0314(13) Uani 0.621(5) 1 d P B 1
N1' N 0.4962(11) 0.592(2) 0.3000(9) 0.036(3) Uani 0.401(5) 1 d PD A 2
N2' N 0.3002(12) 0.4907(13) 0.3203(10) 0.044(3) Uani 0.401(5) 1 d PD A 2
N3' N 0.214(2) 0.546(3) 0.1353(15) 0.029(5) Uani 0.401(5) 1 d PD A 2
N4' N 0.1014(10) 0.5447(9) 0.0140(6) 0.0343(17) Uani 0.401(5) 1 d PD . 2
C1' C 0.4536(11) 0.6248(9) 0.1842(7) 0.043(2) Uani 0.401(5) 1 d PD A 2
C2' C 0.1341(10) 0.4545(8) 0.2158(7) 0.035(2) Uani 0.401(5) 1 d PD A 2
H2' H -0.0180 0.3776 0.1976 0.042 Uiso 0.401(5) 1 calc PR A 2
C3' C 0.7200(15) 0.652(3) 0.3951(13) 0.038(5) Uani 0.401(5) 1 d PD A 2
H3D H 0.7266 0.5732 0.4466 0.046 Uiso 0.401(5) 1 calc PR A 2
H3E H 0.7351 0.7757 0.4581 0.046 Uiso 0.401(5) 1 calc PR A 2
H3F H 0.8499 0.6487 0.3449 0.046 Uiso 0.401(5) 1 calc PR A 2
N5' N 0.4536(11) 0.8808(16) 0.7227(8) 0.035(3) Uani 0.379(5) 1 d PD B 2
N6' N 0.3849(15) 0.8000(15) 0.8110(9) 0.035(3) Uani 0.379(5) 1 d PD B 2
N7' N 0.7580(19) 0.940(2) 0.8768(14) 0.022(3) Uani 0.379(5) 1 d PDU B 2
N8' N 0.9859(10) 1.0221(8) 0.9503(6) 0.0321(17) Uani 0.379(5) 1 d PD . 2
C4' C 0.6812(11) 0.9767(10) 0.7601(6) 0.042(2) Uani 0.379(5) 1 d PD B 2
C5' C 0.5746(12) 0.8447(9) 0.9061(6) 0.039(2) Uani 0.379(5) 1 d PD B 2
H5' H 0.5813 0.8139 0.9846 0.046 Uiso 0.379(5) 1 calc PR B 2
C6' C 0.2835(18) 0.867(3) 0.6072(12) 0.038(6) Uani 0.379(5) 1 d PD B 2
H6D H 0.1554 0.9225 0.6393 0.046 Uiso 0.379(5) 1 calc PR B 2
H6E H 0.2183 0.7395 0.5501 0.046 Uiso 0.379(5) 1 calc PR B 2
H6F H 0.3614 0.9283 0.5538 0.046 Uiso 0.379(5) 1 calc PR B 2
O1' O 0.5883(17) 0.7115(14) 0.1433(10) 0.036(2) Uani 0.401(5) 1 d P A 2
O2' O 0.7893(15) 1.0572(14) 0.7037(10) 0.041(2) Uani 0.379(5) 1 d P B 2


_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
N1 C1 1.354(6) . ?
N1 N2 1.375(6) . ?
N1 C3 1.448(5) . ?
N2 C2 1.298(7) . ?
N3 N4 1.373(6) . ?
N3 C2 1.383(12) . ?
N3 C1 1.391(8) . ?
N4 N4 1.266(8) 2_565 ?
C1 O1 1.222(6) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N5 C4 1.355(5) . ?
N5 N6 1.378(6) . ?
N5 C6 1.444(4) . ?
N6 C5 1.315(7) . ?
N7 C5 1.342(10) . ?
N7 N8 1.385(5) . ?
N7 C4 1.415(7) . ?
N8 N8 1.261(7) 2_777 ?
C4 O2 1.206(6) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N1' C1' 1.352(6) . ?
N1' N2' 1.377(7) . ?
N1' C3' 1.448(5) . ?
N2' C2' 1.297(8) . ?
N3' N4' 1.373(7) . ?
N3' C2' 1.382(12) . ?
N3' C1' 1.392(8) . ?
N4' N4' 1.221(12) 2_565 ?
C1' O1' 1.187(10) . ?
C2' H2' 0.9500 . ?
C3' H3D 0.9800 . ?
C3' H3E 0.9800 . ?
C3' H3F 0.9800 . ?
N5' C4' 1.356(5) . ?
N5' N6' 1.377(6) . ?
N5' C6' 1.443(5) . ?
N6' C5' 1.314(7) . ?
N7' C5' 1.344(11) . ?
N7' N8' 1.385(6) . ?
N7' C4' 1.414(7) . ?
N8' N8' 1.231(12) 2_777 ?
C4' O2' 1.186(12) . ?
C5' H5' 0.9500 . ?
C6' H6D 0.9800 . ?
C6' H6E 0.9800 . ?
C6' H6F 0.9800 . ?

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 112.5(4) . . ?
C1 N1 C3 126.2(7) . . ?
N2 N1 C3 121.1(7) . . ?
C2 N2 N1 106.3(5) . . ?
N4 N3 C2 129.4(6) . . ?
N4 N3 C1 121.1(9) . . ?
C2 N3 C1 109.0(4) . . ?
N4 N4 N3 110.4(7) 2_565 . ?
O1 C1 N1 128.2(4) . . ?
O1 C1 N3 129.0(6) . . ?
N1 C1 N3 102.6(5) . . ?
N2 C2 N3 109.3(4) . . ?
N2 C2 H2 125.4 . . ?
N3 C2 H2 125.4 . . ?
C4 N5 N6 114.0(4) . . ?
C4 N5 C6 125.3(5) . . ?
N6 N5 C6 120.7(5) . . ?
C5 N6 N5 104.6(5) . . ?
C5 N7 N8 131.9(6) . . ?
C5 N7 C4 110.1(4) . . ?
N8 N7 C4 117.4(7) . . ?
N8 N8 N7 109.5(6) 2_777 . ?
O2 C4 N5 130.2(4) . . ?
O2 C4 N7 129.1(5) . . ?
N5 C4 N7 100.7(5) . . ?
N6 C5 N7 110.5(4) . . ?
N6 C5 H5 124.8 . . ?
N7 C5 H5 124.8 . . ?
C1' N1' N2' 112.6(5) . . ?
C1' N1' C3' 125.8(8) . . ?
N2' N1' C3' 121.7(7) . . ?
C2' N2' N1' 106.2(5) . . ?
N4' N3' C2' 129.6(7) . . ?
N4' N3' C1' 120.7(10) . . ?
C2' N3' C1' 109.0(5) . . ?
N4' N4' N3' 109.3(7) 2_565 . ?
O1' C1' N1' 126.9(8) . . ?
O1' C1' N3' 130.4(9) . . ?
N1' C1' N3' 102.5(6) . . ?
N2' C2' N3' 109.2(4) . . ?
N2' C2' H2' 125.4 . . ?
N3' C2' H2' 125.4 . . ?
N1' C3' H3D 109.5 . . ?
N1' C3' H3E 109.5 . . ?
H3D C3' H3E 109.5 . . ?
N1' C3' H3F 109.5 . . ?
H3D C3' H3F 109.5 . . ?
H3E C3' H3F 109.5 . . ?
C4' N5' N6' 114.0(4) . . ?
C4' N5' C6' 126.1(6) . . ?
N6' N5' C6' 119.7(6) . . ?
C5' N6' N5' 104.5(5) . . ?
C5' N7' N8' 130.7(7) . . ?
C5' N7' C4' 109.9(5) . . ?
N8' N7' C4' 118.8(8) . . ?
N8' N8' N7' 108.5(7) 2_777 . ?
O2' C4' N5' 129.1(7) . . ?
O2' C4' N7' 130.0(8) . . ?
N5' C4' N7' 100.7(5) . . ?
N6' C5' N7' 110.6(4) . . ?
N6' C5' H5' 124.7 . . ?
N7' C5' H5' 124.7 . . ?
N5' C6' H6D 109.5 . . ?
N5' C6' H6E 109.5 . . ?
H6D C6' H6E 109.5 . . ?
N5' C6' H6F 109.5 . . ?
H6D C6' H6F 109.5 . . ?
H6E C6' H6F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 0.9(11) . . . . ?
C3 N1 N2 C2 175.5(10) . . . . ?
C2 N3 N4 N4 2.8(15) . . . 2_565 ?
C1 N3 N4 N4 173.9(9) . . . 2_565 ?
N2 N1 C1 O1 178.1(7) . . . . ?
C3 N1 C1 O1 3.8(16) . . . . ?
N2 N1 C1 N3 2.3(11) . . . . ?
C3 N1 C1 N3 -172.0(12) . . . . ?
N4 N3 C1 O1 7.1(16) . . . . ?
C2 N3 C1 O1 179.8(6) . . . . ?
N4 N3 C1 N1 -177.1(10) . . . . ?
C2 N3 C1 N1 -4.4(11) . . . . ?
N1 N2 C2 N3 -3.7(10) . . . . ?
N4 N3 C2 N2 177.2(11) . . . . ?
C1 N3 C2 N2 5.3(11) . . . . ?
C4 N5 N6 C5 -1.4(9) . . . . ?
C6 N5 N6 C5 178.3(8) . . . . ?
C5 N7 N8 N8 8.3(15) . . . 2_777 ?
C4 N7 N8 N8 178.5(8) . . . 2_777 ?
N6 N5 C4 O2 -179.7(7) . . . . ?
C6 N5 C4 O2 0.7(13) . . . . ?
N6 N5 C4 N7 2.4(9) . . . . ?
C6 N5 C4 N7 -177.2(10) . . . . ?
C5 N7 C4 O2 179.5(7) . . . . ?
N8 N7 C4 O2 7.2(15) . . . . ?
C5 N7 C4 N5 -2.6(10) . . . . ?
N8 N7 C4 N5 -174.9(9) . . . . ?
N5 N6 C5 N7 -0.4(9) . . . . ?
N8 N7 C5 N6 172.7(11) . . . . ?
C4 N7 C5 N6 2.0(11) . . . . ?
C1' N1' N2' C2' 1.7(16) . . . . ?
C3' N1' N2' C2' -177.8(16) . . . . ?
C2' N3' N4' N4' 5(3) . . . 2_565 ?
C1' N3' N4' N4' 174.3(15) . . . 2_565 ?
N2' N1' C1' O1' 178.2(11) . . . . ?
C3' N1' C1' O1' -2(2) . . . . ?
N2' N1' C1' N3' 3.0(17) . . . . ?
C3' N1' C1' N3' -177.5(18) . . . . ?
N4' N3' C1' O1' 7(3) . . . . ?
C2' N3' C1' O1' 178.7(11) . . . . ?
N4' N3' C1' N1' -177.9(16) . . . . ?
C2' N3' C1' N1' -6.4(18) . . . . ?
N1' N2' C2' N3' -5.8(16) . . . . ?
N4' N3' C2' N2' 178.4(18) . . . . ?
C1' N3' C2' N2' 7.9(19) . . . . ?
C4' N5' N6' C5' -0.6(15) . . . . ?
C6' N5' N6' C5' -177.2(14) . . . . ?
C5' N7' N8' N8' 8(2) . . . 2_777 ?
C4' N7' N8' N8' 177.5(14) . . . 2_777 ?
N6' N5' C4' O2' 178.6(12) . . . . ?
C6' N5' C4' O2' -5(2) . . . . ?
N6' N5' C4' N7' 3.8(16) . . . . ?
C6' N5' C4' N7' -179.9(17) . . . . ?
C5' N7' C4' O2' 179.6(12) . . . . ?
N8' N7' C4' O2' 8(3) . . . . ?
C5' N7' C4' N5' -5.6(17) . . . . ?
N8' N7' C4' N5' -177.3(15) . . . . ?
N5' N6' C5' N7' -3.2(15) . . . . ?
N8' N7' C5' N6' 176.2(17) . . . . ?
C4' N7' C5' N6' 5.8(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.059


_database_code_depnum_ccdc_archive 'CCDC 978800'
#######################################################################
#
#                 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_added_by_encifer
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H8 Cl2 N10 O8'
_chemical_formula_sum            'C4 H8 Cl2 N10 O8'
_chemical_formula_weight         395.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.9462(9)
_cell_length_b                   7.1522(17)
_cell_length_c                   9.503(2)
_cell_angle_alpha                97.491(7)
_cell_angle_beta                 94.118(8)
_cell_angle_gamma                99.293(8)
_cell_volume                     327.45(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1314
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      29.11

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.569
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            3241
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         29.110
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             1633
_reflns_number_gt                1464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

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

_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.0487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.37(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1633
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.00591(7) 0.74402(5) 0.63663(3) 0.01210(16) Uani 1 1 d . . . . .
O1 O -0.1244(3) 0.78195(18) 0.50425(12) 0.0249(3) Uani 1 1 d . . . . .
O2 O 0.2744(3) 0.71597(18) 0.62326(14) 0.0253(3) Uani 1 1 d . . . . .
O3 O -0.0073(3) 0.90515(16) 0.74579(12) 0.0211(3) Uani 1 1 d . . . . .
O4 O -0.1594(3) 0.57621(17) 0.67864(14) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.3766(3) 0.8279(2) 0.31523(15) 0.0158(3) Uani 1 1 d . . . . .
N2 N 0.4580(3) 0.97677(18) 0.05654(13) 0.0136(3) Uani 1 1 d . . . . .
N3 N 0.5666(3) 0.82201(17) 0.09154(13) 0.0125(3) Uani 1 1 d . . . . .
N4 N 0.6619(3) 0.61391(19) 0.22017(13) 0.0150(3) Uani 1 1 d . . . . .
N5 N 0.7993(3) 0.5859(2) 0.09948(14) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.5222(3) 0.7580(2) 0.21935(15) 0.0119(3) Uani 1 1 d . . . . .
C2 C 0.7406(3) 0.7131(2) 0.02347(16) 0.0169(3) Uani 1 1 d . . . . .
H1 H 0.294(4) 0.911(3) 0.297(2) 0.023(5) Uiso 1 1 d . . . . .
H1A H 0.366(4) 0.787(3) 0.386(2) 0.027(6) Uiso 1 1 d . . . . .
H2 H 0.803(4) 0.725(3) -0.066(2) 0.023(5) Uiso 1 1 d . . . . .
H4 H 0.667(5) 0.539(3) 0.285(2) 0.032(6) 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
Cl1 O1 1.4262(12) . ?
Cl1 O4 1.4320(12) . ?
Cl1 O2 1.4445(12) . ?
Cl1 O3 1.4478(11) . ?
N1 C1 1.3003(19) . ?
N1 H1 0.80(2) . ?
N1 H1A 0.77(2) . ?
N2 N2 1.245(2) 2_675 ?
N2 N3 1.3736(17) . ?
N3 C1 1.3723(18) . ?
N3 C2 1.3898(19) . ?
N4 C1 1.3311(19) . ?
N4 N5 1.3832(18) . ?
N4 H4 0.87(2) . ?
N5 C2 1.288(2) . ?
C2 H2 0.93(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
O1 Cl1 O4 110.82(8) . . ?
O1 Cl1 O2 109.72(8) . . ?
O4 Cl1 O2 109.04(7) . . ?
O1 Cl1 O3 109.33(7) . . ?
O4 Cl1 O3 108.70(8) . . ?
O2 Cl1 O3 109.21(8) . . ?
C1 N1 H1 118.3(14) . . ?
C1 N1 H1A 120.1(16) . . ?
H1 N1 H1A 122(2) . . ?
N2 N2 N3 110.34(15) 2_675 . ?
C1 N3 N2 120.14(12) . . ?
C1 N3 C2 107.78(12) . . ?
N2 N3 C2 131.94(12) . . ?
C1 N4 N5 112.51(13) . . ?
C1 N4 H4 126.8(15) . . ?
N5 N4 H4 120.6(15) . . ?
C2 N5 N4 105.24(12) . . ?
N1 C1 N4 129.65(14) . . ?
N1 C1 N3 126.16(13) . . ?
N4 C1 N3 104.18(12) . . ?
N5 C2 N3 110.25(13) . . ?
N5 C2 H2 123.5(13) . . ?
N3 C2 H2 126.2(13) . . ?

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
N2 N2 N3 C1 173.79(16) 2_675 . . . ?
N2 N2 N3 C2 -1.4(3) 2_675 . . . ?
C1 N4 N5 C2 -0.7(2) . . . . ?
N5 N4 C1 N1 -178.09(16) . . . . ?
N5 N4 C1 N3 1.43(18) . . . . ?
N2 N3 C1 N1 1.7(2) . . . . ?
C2 N3 C1 N1 177.92(17) . . . . ?
N2 N3 C1 N4 -177.88(13) . . . . ?
C2 N3 C1 N4 -1.62(16) . . . . ?
N4 N5 C2 N3 -0.43(19) . . . . ?
C1 N3 C2 N5 1.33(18) . . . . ?
N2 N3 C2 N5 176.98(15) . . . . ?

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
N4 H4 O2 0.87(2) 2.17(2) 2.9946(18) 158(2) 2_666
N4 H4 Cl1 0.87(2) 2.96(2) 3.6445(14) 137.0(18) 2_666
C2 H2 O4 0.93(2) 2.55(2) 3.390(2) 149.7(17) 1_654
C2 H2 O3 0.93(2) 2.49(2) 3.357(2) 154.5(17) 1_654
N1 H1A O2 0.77(2) 2.44(2) 3.1871(19) 167(2) .
N1 H1 O3 0.80(2) 2.14(2) 2.9289(19) 169(2) 2_576

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-3


_database_code_depnum_ccdc_archive 'CCDC 979523'
