# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

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

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc1ly6yp
_database_code_depnum_ccdc_archive 'CCDC 1487843'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(H4 N), C6 N8 O10'
_chemical_formula_sum            'C6 H8 N10 O10'
_chemical_formula_weight         380.22

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1   '

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

_cell_length_a                   6.7135(6)
_cell_length_b                   6.7702(6)
_cell_length_c                   8.1378(7)
_cell_angle_alpha                80.267(3)
_cell_angle_beta                 76.307(3)
_cell_angle_gamma                74.335(3)
_cell_volume                     343.82(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1522
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      25.47

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             194
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3667
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         25.49
_reflns_number_total             1258
_reflns_number_gt                1014
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0407P)²+0.1379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1258
_refine_ls_number_parameters     130
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4438(3) 0.4453(3) 1.0729(2) 0.0139(4) Uani 1 1 d . . .
C2 C 0.2323(3) 0.2658(3) 1.2100(2) 0.0136(4) Uani 1 1 d . . .
C3 C 0.0744(3) 0.1470(3) 1.2390(2) 0.0146(4) Uani 1 1 d . . .
N1 N 0.4771(3) 0.4100(2) 1.22553(19) 0.0187(4) Uani 1 1 d . . .
N2 N 0.3377(3) 0.2887(3) 1.3159(2) 0.0199(4) Uani 1 1 d . . .
N3 N 0.1296(3) -0.0327(2) 1.16041(19) 0.0164(4) Uani 1 1 d . . .
N4 N -0.1047(2) 0.1944(2) 1.36544(19) 0.0151(4) Uani 1 1 d . . .
N5 N 0.6055(3) 0.7739(2) 0.3245(2) 0.0182(4) Uani 1 1 d D . .
H5A H 0.498(2) 0.810(3) 0.4101(19) 0.022 Uiso 1 1 d D . .
H5B H 0.563(3) 0.830(3) 0.2261(18) 0.022 Uiso 1 1 d D . .
H5C H 0.711(2) 0.828(3) 0.327(2) 0.022 Uiso 1 1 d D . .
H5D H 0.644(3) 0.640(2) 0.324(2) 0.022 Uiso 1 1 d D . .
O1 O 0.2904(2) 0.36488(19) 1.05039(15) 0.0146(3) Uani 1 1 d . . .
O2 O 0.0096(2) -0.1464(2) 1.17246(18) 0.0254(4) Uani 1 1 d . . .
O3 O 0.3143(2) -0.0708(2) 1.07049(17) 0.0228(3) Uani 1 1 d . . .
O4 O -0.2205(2) 0.0715(2) 1.42226(16) 0.0209(3) Uani 1 1 d . . .
O5 O -0.1428(2) 0.3626(2) 1.42353(17) 0.0232(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0142(10) 0.0123(9) 0.0161(9) -0.0031(7) -0.0014(8) -0.0049(8)
C2 0.0151(9) 0.0135(9) 0.0113(9) 0.0000(7) 0.0000(7) -0.0049(7)
C3 0.0138(10) 0.0149(9) 0.0143(9) -0.0028(7) 0.0008(7) -0.0047(8)
N1 0.0233(9) 0.0216(9) 0.0144(8) 0.0021(7) -0.0028(7) -0.0142(7)
N2 0.0231(9) 0.0239(9) 0.0168(8) 0.0019(7) -0.0034(7) -0.0157(8)
N3 0.0151(8) 0.0172(8) 0.0173(8) -0.0016(6) -0.0014(7) -0.0061(7)
N4 0.0134(8) 0.0155(8) 0.0163(8) 0.0002(6) -0.0034(6) -0.0040(7)
N5 0.0177(9) 0.0194(9) 0.0192(9) -0.0047(7) -0.0019(7) -0.0074(7)
O1 0.0160(7) 0.0164(7) 0.0133(6) 0.0002(5) -0.0020(5) -0.0093(5)
O2 0.0234(8) 0.0250(8) 0.0325(8) -0.0105(6) 0.0027(6) -0.0163(7)
O3 0.0142(7) 0.0238(8) 0.0283(8) -0.0088(6) 0.0047(6) -0.0051(6)
O4 0.0166(7) 0.0210(7) 0.0237(7) -0.0009(6) 0.0034(6) -0.0099(6)
O5 0.0223(8) 0.0177(7) 0.0294(8) -0.0110(6) -0.0010(6) -0.0034(6)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.286(2) . ?
C1 O1 1.348(2) . ?
C1 C1 1.451(3) 2_667 ?
C2 N2 1.289(2) . ?
C2 O1 1.377(2) . ?
C2 C3 1.451(2) . ?
C3 N4 1.387(2) . ?
C3 N3 1.390(2) . ?
N1 N2 1.406(2) . ?
N3 O2 1.234(2) . ?
N3 O3 1.265(2) . ?
N4 O5 1.2461(19) . ?
N4 O4 1.2494(19) . ?
N5 H5A 0.888(13) . ?
N5 H5B 0.902(13) . ?
N5 H5C 0.886(13) . ?
N5 H5D 0.875(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 O1 114.29(16) . . ?
N1 C1 C1 127.1(2) . 2_667 ?
O1 C1 C1 118.63(19) . 2_667 ?
N2 C2 O1 112.15(16) . . ?
N2 C2 C3 128.24(16) . . ?
O1 C2 C3 119.57(15) . . ?
N4 C3 N3 122.67(16) . . ?
N4 C3 C2 118.99(16) . . ?
N3 C3 C2 117.21(16) . . ?
C1 N1 N2 105.19(15) . . ?
C2 N2 N1 106.69(15) . . ?
O2 N3 O3 121.44(15) . . ?
O2 N3 C3 123.89(16) . . ?
O3 N3 C3 114.66(15) . . ?
O5 N4 O4 121.10(15) . . ?
O5 N4 C3 117.39(15) . . ?
O4 N4 C3 121.49(15) . . ?
H5A N5 H5B 108.4(13) . . ?
H5A N5 H5C 110.2(13) . . ?
H5B N5 H5C 105.9(13) . . ?
H5A N5 H5D 111.2(13) . . ?
H5B N5 H5D 108.3(13) . . ?
H5C N5 H5D 112.7(14) . . ?
C1 O1 C2 101.66(13) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.056
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1487844'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C H8 N5), C6 N8 O10'
_chemical_formula_sum            'C8 H16 N18 O10'
_chemical_formula_weight         524.39

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pbcn '
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   24.125(3)
_cell_length_b                   8.0141(10)
_cell_length_c                   10.8158(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2091.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    168(2)
_cell_measurement_reflns_used    949
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      22.45

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      168(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5897
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.36
_reflns_number_total             1898
_reflns_number_gt                1111
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.2743P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1898
_refine_ls_number_parameters     187
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.40573(11) -0.0119(4) 0.3501(2) 0.0279(7) Uani 1 1 d . . .
C2 C 0.47874(10) -0.0274(4) 0.4571(2) 0.0279(7) Uani 1 1 d . . .
C3 C 0.35649(10) 0.0652(4) 0.3001(2) 0.0268(7) Uani 1 1 d . . .
C4 C 0.34988(12) 0.5941(4) 0.0105(2) 0.0284(7) Uani 1 1 d . . .
N1 N 0.42668(9) -0.1577(3) 0.3287(2) 0.0333(6) Uani 1 1 d . . .
N2 N 0.47513(9) -0.1675(3) 0.4000(2) 0.0309(6) Uani 1 1 d . . .
N3 N 0.36371(9) 0.1841(3) 0.2076(2) 0.0328(6) Uani 1 1 d . . .
N4 N 0.30603(9) 0.0201(3) 0.3456(2) 0.0304(6) Uani 1 1 d . . .
N5 N 0.44206(10) 0.5322(3) 0.0574(2) 0.0385(7) Uani 1 1 d D . .
H5A H 0.4681(10) 0.605(3) 0.075(3) 0.046 Uiso 1 1 d D . .
H5B H 0.4466(12) 0.467(3) 0.125(2) 0.046 Uiso 1 1 d D . .
N6 N 0.39229(9) 0.6164(3) 0.0847(2) 0.0315(6) Uani 1 1 d D . .
H6A H 0.3891(11) 0.679(3) 0.150(2) 0.038 Uiso 1 1 d D . .
N7 N 0.30283(10) 0.6766(3) 0.0284(2) 0.0357(7) Uani 1 1 d D . .
H7A H 0.2718(9) 0.649(4) -0.013(2) 0.043 Uiso 1 1 d D . .
N8 N 0.30036(10) 0.7885(4) 0.1290(2) 0.0350(7) Uani 1 1 d D . .
H8A H 0.2941(11) 0.888(3) 0.095(2) 0.042 Uiso 1 1 d D . .
H8B H 0.2711(8) 0.766(4) 0.175(2) 0.042 Uiso 1 1 d D . .
N9 N 0.35376(10) 0.4924(4) -0.0876(2) 0.0399(7) Uani 1 1 d D . .
H9A H 0.3840(9) 0.431(3) -0.088(3) 0.048 Uiso 1 1 d D . .
H9B H 0.3245(9) 0.461(4) -0.125(3) 0.048 Uiso 1 1 d D . .
O1 O 0.43705(7) 0.0793(2) 0.43204(16) 0.0292(5) Uani 1 1 d . . .
O2 O 0.32537(8) 0.2701(3) 0.16745(18) 0.0423(6) Uani 1 1 d . . .
O3 O 0.41254(8) 0.1988(3) 0.16939(19) 0.0460(6) Uani 1 1 d . . .
O4 O 0.26123(7) 0.0693(3) 0.30058(16) 0.0369(5) Uani 1 1 d . . .
O5 O 0.30641(7) -0.0779(3) 0.43706(17) 0.0372(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0243(14) 0.0276(19) 0.0317(15) -0.0035(14) 0.0050(13) -0.0059(13)
C2 0.0180(14) 0.029(2) 0.0373(16) 0.0011(14) 0.0049(12) 0.0010(13)
C3 0.0236(15) 0.0255(17) 0.0313(15) 0.0038(13) 0.0040(12) -0.0016(13)
C4 0.0297(17) 0.0248(18) 0.0308(15) 0.0036(14) 0.0066(13) -0.0035(14)
N1 0.0276(13) 0.0323(17) 0.0400(14) -0.0043(13) 0.0025(12) 0.0024(11)
N2 0.0247(13) 0.0283(16) 0.0398(13) -0.0054(13) 0.0010(11) 0.0010(11)
N3 0.0315(15) 0.0345(17) 0.0322(14) -0.0025(13) 0.0020(12) -0.0007(12)
N4 0.0278(14) 0.0312(16) 0.0322(13) 0.0001(12) 0.0003(12) 0.0002(12)
N5 0.0247(14) 0.0361(18) 0.0546(17) 0.0033(14) 0.0011(13) -0.0011(12)
N6 0.0250(13) 0.0325(16) 0.0371(13) -0.0016(12) 0.0007(12) -0.0029(11)
N7 0.0276(14) 0.0415(18) 0.0380(14) -0.0080(13) -0.0042(11) -0.0021(13)
N8 0.0315(14) 0.0414(19) 0.0322(15) -0.0048(13) 0.0047(11) -0.0027(13)
N9 0.0356(15) 0.0425(18) 0.0414(15) -0.0038(14) -0.0028(13) 0.0018(14)
O1 0.0247(10) 0.0264(11) 0.0367(11) -0.0032(9) -0.0002(9) 0.0013(9)
O2 0.0406(12) 0.0444(15) 0.0418(12) 0.0129(11) -0.0041(10) 0.0001(11)
O3 0.0334(12) 0.0493(15) 0.0552(13) 0.0102(12) 0.0161(11) -0.0045(11)
O4 0.0246(11) 0.0432(15) 0.0430(11) 0.0061(11) -0.0025(10) 0.0018(10)
O5 0.0310(11) 0.0420(14) 0.0386(11) 0.0120(11) 0.0047(10) 0.0008(10)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.293(4) . ?
C1 O1 1.375(3) . ?
C1 C3 1.444(4) . ?
C2 N2 1.284(3) . ?
C2 O1 1.348(3) . ?
C2 C2 1.452(5) 5_656 ?
C3 N4 1.362(3) . ?
C3 N3 1.393(3) . ?
C4 N6 1.312(3) . ?
C4 N7 1.328(4) . ?
C4 N9 1.341(4) . ?
N1 N2 1.402(3) . ?
N3 O2 1.232(3) . ?
N3 O3 1.254(3) . ?
N4 O4 1.249(3) . ?
N4 O5 1.263(3) . ?
N5 N6 1.409(3) . ?
N5 H5A 0.876(17) . ?
N5 H5B 0.903(17) . ?
N6 H6A 0.870(17) . ?
N7 N8 1.412(3) . ?
N7 H7A 0.901(17) . ?
N8 H8A 0.888(17) . ?
N8 H8B 0.884(17) . ?
N9 H9A 0.881(17) . ?
N9 H9B 0.854(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
N1 C1 O1 112.4(2) . . ?
N1 C1 C3 129.8(3) . . ?
O1 C1 C3 117.8(3) . . ?
N2 C2 O1 114.1(2) . . ?
N2 C2 C2 128.3(3) . 5_656 ?
O1 C2 C2 117.6(3) . 5_656 ?
N4 C3 N3 123.6(2) . . ?
N4 C3 C1 119.1(2) . . ?
N3 C3 C1 117.3(2) . . ?
N6 C4 N7 120.6(3) . . ?
N6 C4 N9 120.8(3) . . ?
N7 C4 N9 118.5(3) . . ?
C1 N1 N2 106.1(2) . . ?
C2 N2 N1 105.8(2) . . ?
O2 N3 O3 122.4(2) . . ?
O2 N3 C3 122.8(2) . . ?
O3 N3 C3 114.7(2) . . ?
O4 N4 O5 120.5(2) . . ?
O4 N4 C3 123.3(2) . . ?
O5 N4 C3 116.2(2) . . ?
N6 N5 H5A 105(2) . . ?
N6 N5 H5B 102.0(18) . . ?
H5A N5 H5B 97(3) . . ?
C4 N6 N5 118.1(2) . . ?
C4 N6 H6A 120.3(19) . . ?
N5 N6 H6A 121.6(19) . . ?
C4 N7 N8 117.7(2) . . ?
C4 N7 H7A 121.2(18) . . ?
N8 N7 H7A 120.3(18) . . ?
N7 N8 H8A 104.7(19) . . ?
N7 N8 H8B 109.6(19) . . ?
H8A N8 H8B 107(3) . . ?
C4 N9 H9A 114(2) . . ?
C4 N9 H9B 120(2) . . ?
H9A N9 H9B 121(3) . . ?
C2 O1 C1 101.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1487846'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C2 H4 N3), C6 N8 O10'
_chemical_formula_sum            'C10 H8 N14 O10'
_chemical_formula_weight         484.30

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1   '

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

_cell_length_a                   7.6518(12)
_cell_length_b                   7.7243(10)
_cell_length_c                   9.0083(12)
_cell_angle_alpha                95.490(4)
_cell_angle_beta                 106.941(4)
_cell_angle_gamma                117.039(4)
_cell_volume                     437.09(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    762
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      25.15

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             246
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4206
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.34
_reflns_number_total             1577
_reflns_number_gt                1058
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0457P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1577
_refine_ls_number_parameters     160
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4485(5) 0.4039(4) 0.7050(3) 0.0286(7) Uani 1 1 d . . .
H1 H 0.5883 0.4454 0.7753 0.034 Uiso 1 1 calc R . .
C2 C 0.1366(5) 0.3626(4) 0.6209(3) 0.0251(7) Uani 1 1 d . . .
H2 H 0.0117 0.3653 0.6143 0.030 Uiso 1 1 calc R . .
C3 C 0.4981(4) 1.0178(4) 0.4220(3) 0.0135(6) Uani 1 1 d . . .
C4 C 0.3709(4) 0.9812(4) 0.1720(3) 0.0150(6) Uani 1 1 d . . .
C5 C 0.2130(4) 0.9065(4) 0.0100(3) 0.0146(6) Uani 1 1 d . . .
N1 N 0.1656(4) 0.2783(3) 0.5061(3) 0.0267(6) Uani 1 1 d D . .
H1A H 0.072(4) 0.216(4) 0.404(3) 0.032 Uiso 1 1 d D . .
N2 N 0.3628(4) 0.3016(3) 0.5555(3) 0.0300(6) Uani 1 1 d . . .
N3 N 0.3127(4) 0.4434(3) 0.7476(2) 0.0247(6) Uani 1 1 d D . .
H3A H 0.332(4) 0.512(4) 0.841(3) 0.030 Uiso 1 1 d D . .
N4 N 0.6547(3) 1.1426(3) 0.3893(2) 0.0191(5) Uani 1 1 d . . .
N5 N 0.5687(4) 1.1168(3) 0.2222(2) 0.0197(5) Uani 1 1 d . . .
N6 N 0.1808(4) 1.0450(3) -0.0639(2) 0.0181(5) Uani 1 1 d . . .
N7 N 0.1356(3) 0.7117(3) -0.0750(2) 0.0159(5) Uani 1 1 d . . .
O1 O 0.3129(3) 0.9093(2) 0.29437(17) 0.0156(4) Uani 1 1 d . . .
O2 O 0.0721(3) 1.0003(3) -0.21027(18) 0.0261(5) Uani 1 1 d . . .
O3 O 0.2678(3) 1.2206(3) 0.02329(19) 0.0276(5) Uani 1 1 d . . .
O4 O -0.0063(3) 0.6304(2) -0.21149(19) 0.0200(4) Uani 1 1 d . . .
O5 O 0.2205(3) 0.6194(2) -0.00461(18) 0.0213(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.025(2) 0.0271(16) 0.0270(16) 0.0030(12) -0.0027(14) 0.0163(15)
C2 0.022(2) 0.0236(16) 0.0260(16) 0.0033(12) 0.0055(14) 0.0117(15)
C3 0.0144(17) 0.0141(14) 0.0090(12) -0.0001(10) 0.0006(11) 0.0078(13)
C4 0.0174(18) 0.0172(14) 0.0126(13) 0.0058(11) 0.0080(12) 0.0087(14)
C5 0.0142(17) 0.0151(14) 0.0113(12) 0.0029(10) 0.0031(11) 0.0060(12)
N1 0.0299(17) 0.0257(14) 0.0147(12) -0.0024(10) -0.0040(11) 0.0155(13)
N2 0.0345(19) 0.0352(15) 0.0221(13) 0.0025(11) 0.0063(12) 0.0227(14)
N3 0.0353(18) 0.0232(13) 0.0121(12) 0.0003(9) 0.0048(12) 0.0154(13)
N4 0.0143(15) 0.0255(13) 0.0097(11) 0.0045(9) 0.0014(10) 0.0059(11)
N5 0.0168(15) 0.0260(13) 0.0120(11) 0.0069(9) 0.0053(10) 0.0072(12)
N6 0.0200(15) 0.0198(12) 0.0143(11) 0.0040(9) 0.0062(10) 0.0101(11)
N7 0.0168(14) 0.0189(12) 0.0138(11) 0.0066(9) 0.0078(10) 0.0087(11)
O1 0.0151(11) 0.0204(10) 0.0096(9) 0.0056(7) 0.0048(8) 0.0073(9)
O2 0.0344(14) 0.0243(11) 0.0100(9) 0.0021(8) -0.0035(9) 0.0150(10)
O3 0.0355(14) 0.0175(10) 0.0202(9) -0.0041(8) -0.0012(9) 0.0147(10)
O4 0.0187(12) 0.0181(10) 0.0108(9) 0.0001(7) -0.0007(8) 0.0042(9)
O5 0.0278(13) 0.0243(10) 0.0187(10) 0.0109(8) 0.0092(9) 0.0175(10)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.296(3) . ?
C1 N3 1.349(4) . ?
C1 H1 0.9500 . ?
C2 N1 1.295(3) . ?
C2 N3 1.308(3) . ?
C2 H2 0.9500 . ?
C3 N4 1.289(3) . ?
C3 O1 1.349(3) . ?
C3 C3 1.452(4) 2_676 ?
C4 N5 1.289(3) . ?
C4 O1 1.377(3) . ?
C4 C5 1.450(3) . ?
C5 N7 1.381(3) . ?
C5 N6 1.388(3) . ?
N1 N2 1.362(3) . ?
N1 H1A 0.90(2) . ?
N3 H3A 0.88(2) . ?
N4 N5 1.408(3) . ?
N6 O2 1.250(2) . ?
N6 O3 1.254(2) . ?
N7 O4 1.240(2) . ?
N7 O5 1.265(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 C1 N3 110.9(3) . . ?
N2 C1 H1 124.5 . . ?
N3 C1 H1 124.5 . . ?
N1 C2 N3 106.7(3) . . ?
N1 C2 H2 126.6 . . ?
N3 C2 H2 126.6 . . ?
N4 C3 O1 114.70(19) . . ?
N4 C3 C3 127.3(3) . 2_676 ?
O1 C3 C3 118.0(3) . 2_676 ?
N5 C4 O1 112.4(2) . . ?
N5 C4 C5 127.8(2) . . ?
O1 C4 C5 119.8(2) . . ?
N7 C5 N6 122.2(2) . . ?
N7 C5 C4 118.2(2) . . ?
N6 C5 C4 118.1(2) . . ?
C2 N1 N2 111.9(2) . . ?
C2 N1 H1A 125.5(19) . . ?
N2 N1 H1A 122.5(19) . . ?
C1 N2 N1 103.1(2) . . ?
C2 N3 C1 107.3(2) . . ?
C2 N3 H3A 123.4(19) . . ?
C1 N3 H3A 129.3(19) . . ?
C3 N4 N5 104.8(2) . . ?
C4 N5 N4 106.78(18) . . ?
O2 N6 O3 120.5(2) . . ?
O2 N6 C5 122.7(2) . . ?
O3 N6 C5 116.80(19) . . ?
O4 N7 O5 121.37(19) . . ?
O4 N7 C5 123.3(2) . . ?
O5 N7 C5 115.37(19) . . ?
C3 O1 C4 101.37(19) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.067
