# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 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
_database_code_depnum_ccdc_archive 'CCDC 1537495'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H3 N11 O5'
_chemical_formula_sum            'C8 H3 N11 O5'
_chemical_formula_weight         333.21

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   11.5408(8)
_cell_length_b                   11.6206(8)
_cell_length_c                   18.3621(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2462.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3069
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      25.35

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_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            12893
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2242
_reflns_number_gt                1502
_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)+(0.0615P)²+2.1439P] 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         2242
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.2048(3) 0.1129(3) 0.29418(18) 0.0234(8) Uani 1 1 d . . .
C2 C 0.2490(3) 0.0209(3) 0.33820(17) 0.0204(8) Uani 1 1 d . . .
C3 C 0.2207(3) -0.0280(3) 0.40973(17) 0.0195(8) Uani 1 1 d . . .
C4 C 0.1615(3) -0.0519(3) 0.52189(18) 0.0194(8) Uani 1 1 d . . .
C5 C -0.0174(3) 0.2838(3) 0.36479(18) 0.0208(8) Uani 1 1 d . . .
C6 C -0.0609(3) 0.3364(3) 0.42843(18) 0.0214(8) Uani 1 1 d . . .
C7 C -0.0282(3) 0.3177(3) 0.50427(19) 0.0220(8) Uani 1 1 d . . .
C8 C 0.0334(3) 0.2385(3) 0.59801(19) 0.0270(9) Uani 1 1 d . . .
N1 N 0.1148(3) 0.1945(2) 0.29965(15) 0.0258(7) Uani 1 1 d . . .
N2 N 0.0720(2) 0.1989(2) 0.36162(14) 0.0205(7) Uani 1 1 d . . .
N3 N 0.2638(3) 0.1188(3) 0.23369(15) 0.0312(8) Uani 1 1 d . . .
N4 N 0.3359(3) -0.0256(3) 0.30299(16) 0.0292(7) Uani 1 1 d . . .
N5 N 0.2619(3) -0.1281(3) 0.42698(15) 0.0290(8) Uani 1 1 d . . .
N6 N 0.1597(2) 0.0213(3) 0.46454(15) 0.0189(7) Uani 1 1 d . . .
H6A H 0.126(3) 0.084(3) 0.4616(18) 0.023 Uiso 1 1 d . . .
N7 N -0.0692(3) 0.3254(3) 0.30799(16) 0.0299(8) Uani 1 1 d . . .
N8 N -0.1402(3) 0.4107(3) 0.41027(17) 0.0331(8) Uani 1 1 d . . .
N9 N -0.0567(3) 0.3918(3) 0.55432(16) 0.0346(8) Uani 1 1 d . . .
N10 N 0.0283(2) 0.2212(2) 0.52731(15) 0.0225(7) Uani 1 1 d . . .
N11 N 0.0771(4) 0.1707(3) 0.64844(18) 0.0438(10) Uani 1 1 d . . .
H11A H 0.092(4) 0.105(4) 0.633(2) 0.053 Uiso 1 1 d . . .
H11B H 0.079(4) 0.199(4) 0.694(2) 0.053 Uiso 1 1 d . . .
O1 O 0.3453(2) 0.0352(2) 0.23880(13) 0.0345(7) Uani 1 1 d . . .
O2 O 0.2257(2) -0.1445(2) 0.50024(12) 0.0270(6) Uani 1 1 d . . .
O3 O 0.1169(2) -0.0459(2) 0.58093(12) 0.0271(6) Uani 1 1 d . . .
O4 O -0.1469(2) 0.4043(2) 0.33484(14) 0.0364(7) Uani 1 1 d . . .
O5 O -0.0137(2) 0.3380(2) 0.61894(13) 0.0383(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.305(4) . ?
C1 N1 1.410(4) . ?
C1 C2 1.433(5) . ?
C2 N4 1.310(4) . ?
C2 C3 1.468(5) . ?
C3 N5 1.295(4) . ?
C3 N6 1.356(4) . ?
C4 O3 1.202(4) . ?
C4 N6 1.354(4) . ?
C4 O2 1.366(4) . ?
C5 N7 1.296(4) . ?
C5 C6 1.411(5) . ?
C5 N2 1.428(4) . ?
C6 N8 1.302(4) . ?
C6 C7 1.459(5) . ?
C7 N9 1.302(4) . ?
C7 N10 1.364(4) . ?
C8 N10 1.315(4) . ?
C8 N11 1.316(5) . ?
C8 O5 1.334(4) . ?
N1 N2 1.242(4) . ?
N3 O1 1.355(4) . ?
N4 O1 1.379(4) . ?
N5 O2 1.421(4) . ?
N6 H6A 0.83(4) . ?
N7 O4 1.374(4) . ?
N8 O4 1.389(4) . ?
N9 O5 1.430(4) . ?
N11 H11A 0.84(5) . ?
N11 H11B 0.90(4) . ?

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
N3 C1 N1 114.2(3) . . ?
N3 C1 C2 109.5(3) . . ?
N1 C1 C2 136.3(3) . . ?
N4 C2 C1 107.6(3) . . ?
N4 C2 C3 116.8(3) . . ?
C1 C2 C3 135.6(3) . . ?
N5 C3 N6 112.9(3) . . ?
N5 C3 C2 119.0(3) . . ?
N6 C3 C2 128.0(3) . . ?
O3 C4 N6 131.1(3) . . ?
O3 C4 O2 122.7(3) . . ?
N6 C4 O2 106.1(3) . . ?
N7 C5 C6 109.9(3) . . ?
N7 C5 N2 123.9(3) . . ?
C6 C5 N2 126.1(3) . . ?
N8 C6 C5 109.0(3) . . ?
N8 C6 C7 121.7(3) . . ?
C5 C6 C7 129.4(3) . . ?
N9 C7 N10 116.5(3) . . ?
N9 C7 C6 120.7(3) . . ?
N10 C7 C6 122.8(3) . . ?
N10 C8 N11 128.3(3) . . ?
N10 C8 O5 113.5(3) . . ?
N11 C8 O5 118.2(3) . . ?
N2 N1 C1 112.7(3) . . ?
N1 N2 C5 110.7(3) . . ?
C1 N3 O1 105.4(3) . . ?
C2 N4 O1 105.7(3) . . ?
C3 N5 O2 104.2(3) . . ?
C4 N6 C3 107.7(3) . . ?
C4 N6 H6A 128(2) . . ?
C3 N6 H6A 125(2) . . ?
C5 N7 O4 105.1(3) . . ?
C6 N8 O4 105.0(3) . . ?
C7 N9 O5 102.1(3) . . ?
C8 N10 C7 101.6(3) . . ?
C8 N11 H11A 112(3) . . ?
C8 N11 H11B 116(3) . . ?
H11A N11 H11B 131(4) . . ?
N3 O1 N4 111.8(2) . . ?
C4 O2 N5 109.2(2) . . ?
N7 O4 N8 110.9(2) . . ?
C8 O5 N9 106.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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 1537496'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 N12 O5, H2 O'
_chemical_formula_sum            'C8 H6 N12 O6'
_chemical_formula_weight         366.25

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                   8.3476(6)
_cell_length_b                   9.6589(7)
_cell_length_c                   9.7715(8)
_cell_angle_alpha                105.546(3)
_cell_angle_beta                 97.600(2)
_cell_angle_gamma                111.740(2)
_cell_volume                     681.05(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2139
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      25.24

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_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            6298
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0768
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.42
_reflns_number_total             2466
_reflns_number_gt                1644
_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+0.5487P] 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         2466
_refine_ls_number_parameters     253
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7583(4) 1.2506(4) 0.1454(3) 0.0183(7) Uani 1 1 d . . .
C2 C 0.8133(4) 1.1322(4) 0.0780(3) 0.0188(7) Uani 1 1 d . . .
C3 C 0.7825(4) 0.9747(4) 0.0902(3) 0.0186(7) Uani 1 1 d . . .
C4 C 0.7960(4) 0.8034(4) 0.1737(3) 0.0167(7) Uani 1 1 d . . .
C5 C 0.4306(4) 1.0996(4) 0.3311(3) 0.0179(7) Uani 1 1 d . . .
C6 C 0.3312(4) 0.9561(4) 0.3543(3) 0.0179(7) Uani 1 1 d . . .
C7 C 0.2890(4) 0.5707(4) 0.2967(4) 0.0204(7) Uani 1 1 d . . .
C8 C 0.3361(4) 0.8013(4) 0.3094(3) 0.0175(7) Uani 1 1 d . . .
N1 N 0.6412(3) 1.2495(3) 0.2410(3) 0.0192(6) Uani 1 1 d . . .
N2 N 0.5546(3) 1.1115(3) 0.2478(3) 0.0197(6) Uani 1 1 d . . .
N3 N 0.8238(3) 1.3729(3) 0.1054(3) 0.0237(7) Uani 1 1 d . . .
N4 N 0.9130(3) 1.1849(3) -0.0049(3) 0.0236(7) Uani 1 1 d . . .
N5 N 0.6952(4) 0.8474(3) -0.0248(3) 0.0246(7) Uani 1 1 d . . .
N6 N 0.8488(3) 0.9585(3) 0.2175(3) 0.0168(6) Uani 1 1 d . . .
N7 N 0.8248(4) 0.7155(4) 0.2479(3) 0.0238(7) Uani 1 1 d . . .
H7A H 0.782(5) 0.616(4) 0.207(4) 0.029 Uiso 1 1 d . . .
H7B H 0.881(5) 0.762(4) 0.341(4) 0.029 Uiso 1 1 d . . .
N8 N 0.3834(4) 1.2110(3) 0.3979(3) 0.0239(7) Uani 1 1 d . . .
N9 N 0.2244(4) 0.9799(3) 0.4344(3) 0.0236(7) Uani 1 1 d . . .
N10 N 0.4365(4) 0.7716(3) 0.2244(3) 0.0258(7) Uani 1 1 d . . .
N11 N 0.2407(3) 0.6828(3) 0.3566(3) 0.0196(6) Uani 1 1 d . . .
N12 N 0.2385(4) 0.4279(3) 0.3044(4) 0.0295(8) Uani 1 1 d . . .
H12A H 0.169(5) 0.397(4) 0.367(4) 0.035 Uiso 1 1 d . . .
H12B H 0.293(5) 0.375(4) 0.274(4) 0.035 Uiso 1 1 d . . .
O1 O 0.6305(3) 1.3760(3) 0.2987(3) 0.0295(6) Uani 1 1 d . . .
O2 O 0.9211(3) 1.3349(3) 0.0117(3) 0.0280(6) Uani 1 1 d . . .
O3 O 0.7019(3) 0.7277(2) 0.0320(2) 0.0230(5) Uani 1 1 d . . .
O4 O 0.2547(3) 1.1367(3) 0.4611(2) 0.0277(6) Uani 1 1 d . . .
O5 O 0.4038(3) 0.6129(3) 0.2139(3) 0.0301(6) Uani 1 1 d . . .
O6 O 0.0179(3) 0.7195(3) 0.5558(3) 0.0298(6) Uani 1 1 d D . .
H6A H 0.058(4) 0.818(2) 0.597(4) 0.036 Uiso 1 1 d D . .
H6B H 0.076(4) 0.705(4) 0.497(3) 0.036 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
C1 N3 1.294(4) . ?
C1 C2 1.420(4) . ?
C1 N1 1.437(4) . ?
C2 N4 1.301(4) . ?
C2 C3 1.487(4) . ?
C3 N5 1.298(4) . ?
C3 N6 1.365(4) . ?
C4 N7 1.319(4) . ?
C4 N6 1.319(4) . ?
C4 O3 1.347(4) . ?
C5 N8 1.321(4) . ?
C5 N2 1.389(4) . ?
C5 C6 1.424(4) . ?
C6 N9 1.303(4) . ?
C6 C8 1.459(4) . ?
C7 N12 1.310(4) . ?
C7 N11 1.314(4) . ?
C7 O5 1.354(4) . ?
C8 N10 1.307(4) . ?
C8 N11 1.365(4) . ?
N1 O1 1.243(3) . ?
N1 N2 1.285(3) . ?
N3 O2 1.368(3) . ?
N4 O2 1.389(3) . ?
N5 O3 1.425(3) . ?
N7 H7A 0.85(4) . ?
N7 H7B 0.87(4) . ?
N8 O4 1.376(3) . ?
N9 O4 1.384(3) . ?
N10 O5 1.426(3) . ?
N12 H12A 0.93(4) . ?
N12 H12B 0.83(4) . ?
O6 H6A 0.835(18) . ?
O6 H6B 0.820(18) . ?

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
N3 C1 C2 110.8(3) . . ?
N3 C1 N1 118.8(3) . . ?
C2 C1 N1 130.3(3) . . ?
N4 C2 C1 107.8(3) . . ?
N4 C2 C3 119.5(3) . . ?
C1 C2 C3 132.7(3) . . ?
N5 C3 N6 118.1(3) . . ?
N5 C3 C2 119.5(3) . . ?
N6 C3 C2 122.4(3) . . ?
N7 C4 N6 129.3(3) . . ?
N7 C4 O3 117.1(3) . . ?
N6 C4 O3 113.7(3) . . ?
N8 C5 N2 128.0(3) . . ?
N8 C5 C6 109.4(3) . . ?
N2 C5 C6 122.6(3) . . ?
N9 C6 C5 108.9(3) . . ?
N9 C6 C8 119.5(3) . . ?
C5 C6 C8 131.6(3) . . ?
N12 C7 N11 129.1(3) . . ?
N12 C7 O5 118.2(3) . . ?
N11 C7 O5 112.8(3) . . ?
N10 C8 N11 117.0(3) . . ?
N10 C8 C6 121.0(3) . . ?
N11 C8 C6 122.0(3) . . ?
O1 N1 N2 129.2(3) . . ?
O1 N1 C1 117.4(2) . . ?
N2 N1 C1 113.3(2) . . ?
N1 N2 C5 116.4(2) . . ?
C1 N3 O2 104.6(2) . . ?
C2 N4 O2 105.6(2) . . ?
C3 N5 O3 101.5(2) . . ?
C4 N6 C3 100.4(3) . . ?
C4 N7 H7A 120(2) . . ?
C4 N7 H7B 118(2) . . ?
H7A N7 H7B 121(3) . . ?
C5 N8 O4 104.4(2) . . ?
C6 N9 O4 105.3(2) . . ?
C8 N10 O5 101.6(2) . . ?
C7 N11 C8 101.8(2) . . ?
C7 N12 H12A 121(2) . . ?
C7 N12 H12B 119(2) . . ?
H12A N12 H12B 117(3) . . ?
N3 O2 N4 111.3(2) . . ?
C4 O3 N5 106.4(2) . . ?
N8 O4 N9 111.9(2) . . ?
C7 O5 N10 106.8(2) . . ?
H6A O6 H6B 107(4) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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 1537498'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(H4 N), C8 N10 O6'
_chemical_formula_sum            'C8 H8 N12 O6'
_chemical_formula_weight         368.26

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   4.7289(6)
_cell_length_b                   10.5845(12)
_cell_length_c                   14.3425(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.185(5)
_cell_angle_gamma                90
_cell_volume                     717.88(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    1046
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      25.34


_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4148
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.840
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1312
_reflns_number_gt                947
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.3627P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1312
_refine_ls_number_parameters     130
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.6483(5) 0.5274(2) 0.89019(18) 0.0135(6) Uani 1 1 d . . . . .
C2 C 0.6048(5) 0.5079(2) 0.79301(18) 0.0122(6) Uani 1 1 d . . . . .
C3 C 0.3977(5) 0.4324(2) 0.74220(17) 0.0118(6) Uani 1 1 d . . . . .
C4 C 0.1705(5) 0.3547(2) 0.62918(18) 0.0137(6) Uani 1 1 d . . . . .
N1 N 0.4887(5) 0.4706(2) 0.96241(14) 0.0173(6) Uani 1 1 d . . . . .
N2 N 0.8631(5) 0.6027(2) 0.90315(16) 0.0198(6) Uani 1 1 d . . . . .
N3 N 0.7909(5) 0.5751(2) 0.74709(15) 0.0172(5) Uani 1 1 d . . . . .
N4 N 0.2193(4) 0.3580(2) 0.78558(15) 0.0155(5) Uani 1 1 d . . . . .
N5 N 0.3782(4) 0.4363(2) 0.64795(14) 0.0133(5) Uani 1 1 d . . . . .
N6 N -0.4174(5) 0.3181(2) 0.44419(15) 0.0161(5) Uani 1 1 d D . . . .
H6A H -0.272(4) 0.315(2) 0.4871(13) 0.019 Uiso 1 1 d D U . . .
H6B H -0.587(4) 0.308(2) 0.4739(14) 0.019 Uiso 1 1 d D U . . .
H6C H -0.415(5) 0.3953(16) 0.4153(14) 0.019 Uiso 1 1 d D U . . .
H6D H -0.390(4) 0.2559(18) 0.4010(13) 0.019 Uiso 1 1 d D U . . .
O1 O 0.9543(4) 0.63334(17) 0.81495(13) 0.0208(5) Uani 1 1 d . . . . .
O2 O 0.0616(4) 0.30523(17) 0.71057(12) 0.0162(5) Uani 1 1 d . . . . .
O3 O 0.0762(4) 0.31875(19) 0.55315(12) 0.0214(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.304(3) . ?
C1 N1 1.418(3) . ?
C1 C2 1.423(3) . ?
C2 N3 1.311(3) . ?
C2 C3 1.457(3) . ?
C3 N4 1.313(3) . ?
C3 N5 1.355(3) . ?
C4 O3 1.237(3) . ?
C4 N5 1.334(3) . ?
C4 O2 1.381(3) . ?
N1 N1 1.250(4) 3_667 ?
N2 O1 1.376(3) . ?
N3 O1 1.385(3) . ?
N4 O2 1.421(3) . ?
N6 H6A 0.921(15) . ?
N6 H6B 0.915(15) . ?
N6 H6C 0.917(15) . ?
N6 H6D 0.913(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 124.9(2) . . ?
N2 C1 C2 109.8(2) . . ?
N1 C1 C2 125.3(2) . . ?
N3 C2 C1 108.5(2) . . ?
N3 C2 C3 119.8(2) . . ?
C1 C2 C3 131.6(2) . . ?
N4 C3 N5 116.7(2) . . ?
N4 C3 C2 121.6(2) . . ?
N5 C3 C2 121.7(2) . . ?
O3 C4 N5 129.8(2) . . ?
O3 C4 O2 119.6(2) . . ?
N5 C4 O2 110.5(2) . . ?
N1 N1 C1 112.0(3) 3_667 . ?
C1 N2 O1 105.0(2) . . ?
C2 N3 O1 105.2(2) . . ?
C3 N4 O2 102.32(19) . . ?
C4 N5 C3 103.3(2) . . ?
H6A N6 H6B 109.6(14) . . ?
H6A N6 H6C 108.9(15) . . ?
H6B N6 H6C 109.3(14) . . ?
H6A N6 H6D 108.7(14) . . ?
H6B N6 H6D 110.7(15) . . ?
H6C N6 H6D 109.6(15) . . ?
N2 O1 N3 111.44(18) . . ?
C4 O2 N4 107.16(18) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.071



####################################################################### 
# 
# 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 1537497'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(H5 N2), C8 H2 N10 O6'
_chemical_formula_sum            'C8 H12 N14 O6'
_chemical_formula_weight         400.32

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   15.8351(17)
_cell_length_b                   7.8057(8)
_cell_length_c                   12.8372(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.495(4)
_cell_angle_gamma                90
_cell_volume                     1504.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1339
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      25.23

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4332
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         25.355
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1379
_reflns_number_gt                1027
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.9008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1379
_refine_ls_number_parameters     145
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.39208(15) 0.8451(3) 0.72562(18) 0.0209(5) Uani 1 1 d . . . . .
C2 C 0.30130(15) 0.8461(3) 0.65722(17) 0.0169(5) Uani 1 1 d . . . . .
C3 C 0.26115(14) 0.9464(3) 0.55752(17) 0.0157(5) Uani 1 1 d . . . . .
C4 C 0.16824(15) 1.0642(3) 0.42158(17) 0.0188(5) Uani 1 1 d . . . . .
N1 N 0.45871(13) 0.9395(3) 0.70927(17) 0.0345(6) Uani 1 1 d D . . . .
H1A H 0.4490(19) 1.014(3) 0.6604(19) 0.041 Uiso 1 1 d D U . . .
N2 N 0.40116(13) 0.7369(3) 0.80668(16) 0.0269(5) Uani 1 1 d . . . . .
N3 N 0.25600(13) 0.7394(3) 0.69615(15) 0.0225(5) Uani 1 1 d . . . . .
N4 N 0.31352(12) 1.0240(3) 0.51184(15) 0.0208(5) Uani 1 1 d . . . . .
N5 N 0.17227(12) 0.9639(2) 0.50733(15) 0.0188(5) Uani 1 1 d . . . . .
N6 N 0.94277(13) 0.1657(3) 0.37880(16) 0.0229(5) Uani 1 1 d D . . . .
H6A H 0.9987(11) 0.118(2) 0.3839(16) 0.027 Uiso 1 1 d D U . . .
H6B H 0.9169(13) 0.100(2) 0.4159(16) 0.027 Uiso 1 1 d D U . . .
H6C H 0.9111(12) 0.178(3) 0.3085(12) 0.027 Uiso 1 1 d D U . . .
N7 N 0.96307(14) 0.3319(3) 0.42951(19) 0.0305(5) Uani 1 1 d D . . . .
H7A H 0.9111(13) 0.376(3) 0.430(2) 0.037 Uiso 1 1 d D U . . .
H7B H 0.9991(17) 0.301(3) 0.4962(17) 0.037 Uiso 1 1 d D U . . .
O1 O 0.31578(11) 0.6677(2) 0.78723(13) 0.0275(4) Uani 1 1 d . . . . .
O2 O 0.25255(10) 1.1050(2) 0.42021(12) 0.0231(4) Uani 1 1 d . . . . .
O3 O 0.10325(10) 1.1206(2) 0.34812(12) 0.0266(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
C1 N2 1.312(3) . ?
C1 N1 1.357(3) . ?
C1 C2 1.427(3) . ?
C2 N3 1.298(3) . ?
C2 C3 1.462(3) . ?
C3 N4 1.307(3) . ?
C3 N5 1.356(3) . ?
C4 O3 1.236(3) . ?
C4 N5 1.336(3) . ?
C4 O2 1.378(3) . ?
N1 N1 1.391(4) 2_656 ?
N1 H1A 0.834(17) . ?
N2 O1 1.403(3) . ?
N3 O1 1.369(2) . ?
N4 O2 1.413(2) . ?
N6 N7 1.441(3) . ?
N6 H6A 0.944(14) . ?
N6 H6B 0.884(14) . ?
N6 H6C 0.887(14) . ?
N7 H7A 0.893(17) . ?
N7 H7B 0.899(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
N2 C1 N1 125.3(2) . . ?
N2 C1 C2 109.1(2) . . ?
N1 C1 C2 125.6(2) . . ?
N3 C2 C1 109.3(2) . . ?
N3 C2 C3 122.7(2) . . ?
C1 C2 C3 128.0(2) . . ?
N4 C3 N5 116.8(2) . . ?
N4 C3 C2 118.6(2) . . ?
N5 C3 C2 124.6(2) . . ?
O3 C4 N5 130.4(2) . . ?
O3 C4 O2 118.93(19) . . ?
N5 C4 O2 110.64(18) . . ?
C1 N1 N1 118.4(2) . 2_656 ?
C1 N1 H1A 122(2) . . ?
N1 N1 H1A 118(2) 2_656 . ?
C1 N2 O1 104.45(18) . . ?
C2 N3 O1 105.91(18) . . ?
C3 N4 O2 102.58(17) . . ?
C4 N5 C3 102.82(18) . . ?
N7 N6 H6A 104.7(12) . . ?
N7 N6 H6B 110.7(13) . . ?
H6A N6 H6B 108.6(16) . . ?
N7 N6 H6C 109.7(13) . . ?
H6A N6 H6C 109.2(15) . . ?
H6B N6 H6C 113.6(16) . . ?
N6 N7 H7A 106.1(18) . . ?
N6 N7 H7B 99.8(18) . . ?
H7A N7 H7B 114(3) . . ?
N3 O1 N2 111.16(16) . . ?
C4 O2 N4 107.16(16) . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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 1537499'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 N12 O7'
_chemical_formula_sum            'C8 H8 N12 O7'
_chemical_formula_weight         384.26

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   4.5880(4)
_cell_length_b                   11.0597(10)
_cell_length_c                   14.3951(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.645(5)
_cell_angle_gamma                90
_cell_volume                     730.13(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    1236
_cell_measurement_theta_min      3.95
_cell_measurement_theta_max      25.22

_exptl_crystal_description       column
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3991
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.831
_diffrn_reflns_theta_max         25.351
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1340
_reflns_number_gt                1025
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.4685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1340
_refine_ls_number_parameters     139
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.037
_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
C1 C 0.6653(5) -0.0354(2) 0.11070(15) 0.0214(5) Uani 1 1 d . . . . .
C2 C 0.6068(5) -0.02066(19) 0.20627(15) 0.0173(5) Uani 1 1 d . . . . .
C3 C 0.3953(4) 0.05425(19) 0.25387(14) 0.0171(5) Uani 1 1 d . . . . .
C4 C 0.1584(5) 0.1277(2) 0.36355(16) 0.0240(5) Uani 1 1 d . . . . .
N1 N 0.5385(4) 0.03103(18) 0.03551(12) 0.0257(5) Uani 1 1 d . . . . .
N2 N 0.8746(4) -0.11275(19) 0.10013(14) 0.0288(5) Uani 1 1 d . . . . .
N3 N 0.7821(4) -0.09231(17) 0.25381(13) 0.0234(5) Uani 1 1 d . . . . .
N4 N 0.2160(4) 0.12683(18) 0.20857(12) 0.0218(5) Uani 1 1 d . . . . .
N5 N 0.3719(4) 0.04872(17) 0.34709(12) 0.0217(5) Uani 1 1 d . . . . .
N6 N 0.0751(4) 0.32184(18) 0.05328(13) 0.0226(5) Uani 1 1 d D . . . .
H6A H 0.106(4) 0.2585(15) 0.0934(12) 0.027 Uiso 1 1 d D U . . .
H6B H 0.086(4) 0.3925(14) 0.0879(12) 0.027 Uiso 1 1 d D U . . .
H6C H 0.217(4) 0.3241(18) 0.0101(12) 0.027 Uiso 1 1 d D U . . .
H6D H -0.104(3) 0.3155(18) 0.0249(13) 0.027 Uiso 1 1 d D U . . .
O1 O 0.5466(8) 0.1387(3) 0.0471(2) 0.0328(8) Uani 0.5 1 d . . P . .
O2 O 0.9505(3) -0.14916(15) 0.18863(11) 0.0294(4) Uani 1 1 d . . . . .
O3 O 0.0524(3) 0.17728(14) 0.28137(10) 0.0241(4) Uani 1 1 d . . . . .
O4 O 0.0580(4) 0.16097(18) 0.43767(11) 0.0381(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.298(3) . ?
C1 C2 1.419(3) . ?
C1 N1 1.419(3) . ?
C2 N3 1.308(3) . ?
C2 C3 1.461(3) . ?
C3 N4 1.310(3) . ?
C3 N5 1.351(3) . ?
C4 O4 1.231(3) . ?
C4 N5 1.339(3) . ?
C4 O3 1.380(3) . ?
N1 O1 1.203(4) . ?
N1 N1 1.273(4) 3_655 ?
N2 O2 1.371(3) . ?
N3 O2 1.383(2) . ?
N4 O3 1.421(2) . ?
N6 H6A 0.916(14) . ?
N6 H6B 0.927(14) . ?
N6 H6C 0.914(14) . ?
N6 H6D 0.910(14) . ?

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 C2 110.5(2) . . ?
N2 C1 N1 122.7(2) . . ?
C2 C1 N1 126.5(2) . . ?
N3 C2 C1 107.88(19) . . ?
N3 C2 C3 120.31(19) . . ?
C1 C2 C3 131.8(2) . . ?
N4 C3 N5 117.12(19) . . ?
N4 C3 C2 122.00(19) . . ?
N5 C3 C2 120.86(19) . . ?
O4 C4 N5 130.0(2) . . ?
O4 C4 O3 119.5(2) . . ?
N5 C4 O3 110.45(18) . . ?
O1 N1 N1 130.7(3) . 3_655 ?
O1 N1 C1 113.4(2) . . ?
N1 N1 C1 115.6(2) 3_655 . ?
C1 N2 O2 104.68(18) . . ?
C2 N3 O2 105.51(18) . . ?
C3 N4 O3 102.19(16) . . ?
C4 N5 C3 103.04(18) . . ?
H6A N6 H6B 107.5(13) . . ?
H6A N6 H6C 110.4(14) . . ?
H6B N6 H6C 108.3(14) . . ?
H6A N6 H6D 110.3(14) . . ?
H6B N6 H6D 109.9(14) . . ?
H6C N6 H6D 110.4(14) . . ?
N2 O2 N3 111.39(16) . . ?
C4 O3 N4 107.19(16) . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.061



