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

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

data_shrv320
_database_code_depnum_ccdc_archive 'CCDC 1419915'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2015-10-13 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         'C4 H3 N7 O4, H2 O'
_chemical_formula_sum            'C4 H5 N7 O5'
_chemical_formula_weight         231.15

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                   6.5964(3)
_cell_length_b                   7.4775(3)
_cell_length_c                   17.4904(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.043(2)
_cell_angle_gamma                90
_cell_volume                     856.20(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1580
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      22.77

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6788
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7971
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.188
_diffrn_reflns_theta_max         26.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1763
_reflns_number_gt                1196
_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)+(0.0467P)²+0.0997P] 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         1763
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
N1 N 1.3839(3) 0.5064(3) 0.71084(10) 0.0429(5) Uani 1 1 d . . . . .
H1A H 1.390(3) 0.469(3) 0.7592(13) 0.051 Uiso 1 1 d . U . . .
H1B H 1.468(3) 0.574(3) 0.6900(13) 0.051 Uiso 1 1 d . U . . .
C2 C 1.2237(3) 0.4610(2) 0.66470(10) 0.0317(4) Uani 1 1 d . . . . .
N3 N 1.1693(2) 0.4962(2) 0.59126(9) 0.0355(4) Uani 1 1 d . . . . .
H3 H 1.230(3) 0.558(3) 0.5607(12) 0.043 Uiso 1 1 d . U . . .
N4 N 0.9826(2) 0.4176(2) 0.56663(8) 0.0372(4) Uani 1 1 d . . . . .
C5 C 0.9354(3) 0.3393(3) 0.62623(10) 0.0320(4) Uani 1 1 d . . . . .
O6 O 1.07882(18) 0.35819(18) 0.68971(6) 0.0349(3) Uani 1 1 d . . . . .
C7 C 0.7504(3) 0.2401(3) 0.63376(10) 0.0334(4) Uani 1 1 d . . . . .
N8 N 0.7241(2) 0.1647(3) 0.69869(9) 0.0455(5) Uani 1 1 d . . . . .
O9 O 0.5354(2) 0.0877(2) 0.68610(8) 0.0519(4) Uani 1 1 d . . . . .
N10 N 0.4431(2) 0.1177(2) 0.61037(9) 0.0434(4) Uani 1 1 d . . . . .
C11 C 0.5761(3) 0.2125(3) 0.57743(10) 0.0327(4) Uani 1 1 d . . . . .
N12 N 0.5683(2) 0.2825(2) 0.50448(8) 0.0344(4) Uani 1 1 d . . . . .
N13 N 0.3970(2) 0.2498(2) 0.45763(9) 0.0390(4) Uani 1 1 d . . . . .
O14 O 0.2548(2) 0.1587(2) 0.47723(8) 0.0508(4) Uani 1 1 d . . . . .
O15 O 0.3855(2) 0.3169(2) 0.39190(8) 0.0555(4) Uani 1 1 d . . . . .
O1S O 0.9082(3) 0.0976(3) 0.36395(9) 0.0584(5) Uani 1 1 d . . . . .
H1S H 0.830(5) 0.040(4) 0.3889(17) 0.088 Uiso 1 1 d . U . . .
H2S H 1.005(5) 0.120(4) 0.3914(17) 0.088 Uiso 1 1 d . U . . .

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
N1 0.0421(10) 0.0521(12) 0.0325(9) -0.0004(8) -0.0033(8) -0.0117(8)
C2 0.0321(9) 0.0320(11) 0.0301(9) -0.0040(8) -0.0002(8) 0.0014(8)
N3 0.0325(9) 0.0429(10) 0.0297(8) 0.0036(7) -0.0019(7) -0.0071(7)
N4 0.0316(9) 0.0457(10) 0.0327(8) 0.0052(7) -0.0019(7) -0.0051(7)
C5 0.0297(9) 0.0388(12) 0.0263(9) -0.0002(8) -0.0015(8) 0.0045(8)
O6 0.0319(7) 0.0441(8) 0.0274(6) 0.0013(6) -0.0014(5) -0.0033(6)
C7 0.0311(9) 0.0369(11) 0.0318(9) 0.0027(8) 0.0028(8) 0.0032(8)
N8 0.0355(9) 0.0599(12) 0.0410(9) 0.0124(9) 0.0035(8) -0.0037(8)
O9 0.0422(8) 0.0696(11) 0.0434(8) 0.0187(7) 0.0035(7) -0.0104(7)
N10 0.0372(9) 0.0502(11) 0.0423(9) 0.0081(8) 0.0024(8) -0.0060(8)
C11 0.0303(9) 0.0318(11) 0.0363(10) 0.0027(8) 0.0057(8) 0.0011(8)
N12 0.0271(8) 0.0411(10) 0.0331(8) -0.0002(7) -0.0038(7) -0.0035(7)
N13 0.0330(9) 0.0466(10) 0.0368(9) -0.0059(8) 0.0018(7) -0.0023(8)
O14 0.0342(8) 0.0678(11) 0.0491(8) -0.0029(8) -0.0001(7) -0.0171(7)
O15 0.0478(9) 0.0832(12) 0.0330(8) 0.0066(8) -0.0055(7) -0.0074(8)
O1S 0.0428(9) 0.0859(13) 0.0448(9) -0.0130(9) -0.0016(7) -0.0151(9)

_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 C2 1.294(2) . ?
N1 H1A 0.89(2) . ?
N1 H1B 0.86(2) . ?
C2 N3 1.317(2) . ?
C2 O6 1.341(2) . ?
N3 N4 1.385(2) . ?
N3 H3 0.84(2) . ?
N4 C5 1.267(2) . ?
C5 O6 1.375(2) . ?
C5 C7 1.448(3) . ?
C7 N8 1.298(2) . ?
C7 C11 1.434(2) . ?
N8 O9 1.364(2) . ?
O9 N10 1.406(2) . ?
N10 C11 1.315(2) . ?
C11 N12 1.374(2) . ?
N12 N13 1.334(2) . ?
N13 O14 1.241(2) . ?
N13 O15 1.248(2) . ?
O1S H1S 0.84(3) . ?
O1S H2S 0.77(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 116.5(14) . . ?
C2 N1 H1B 114.1(14) . . ?
H1A N1 H1B 129(2) . . ?
N1 C2 N3 131.30(19) . . ?
N1 C2 O6 120.48(16) . . ?
N3 C2 O6 108.22(15) . . ?
C2 N3 N4 110.15(16) . . ?
C2 N3 H3 129.2(14) . . ?
N4 N3 H3 120.6(14) . . ?
C5 N4 N3 103.83(14) . . ?
N4 C5 O6 113.73(16) . . ?
N4 C5 C7 127.34(16) . . ?
O6 C5 C7 118.91(15) . . ?
C2 O6 C5 104.06(13) . . ?
N8 C7 C11 110.87(16) . . ?
N8 C7 C5 120.44(16) . . ?
C11 C7 C5 128.67(16) . . ?
C7 N8 O9 105.03(15) . . ?
N8 O9 N10 111.47(13) . . ?
C11 N10 O9 105.26(15) . . ?
N10 C11 N12 131.40(17) . . ?
N10 C11 C7 107.37(16) . . ?
N12 C11 C7 121.22(16) . . ?
N13 N12 C11 115.63(15) . . ?
O14 N13 O15 120.82(16) . . ?
O14 N13 N12 122.88(16) . . ?
O15 N13 N12 116.30(16) . . ?
H1S O1S H2S 108(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 N3 N4 180.0(2) . . . . ?
O6 C2 N3 N4 0.9(2) . . . . ?
C2 N3 N4 C5 -0.2(2) . . . . ?
N3 N4 C5 O6 -0.5(2) . . . . ?
N3 N4 C5 C7 177.87(18) . . . . ?
N1 C2 O6 C5 179.68(18) . . . . ?
N3 C2 O6 C5 -1.14(19) . . . . ?
N4 C5 O6 C2 1.1(2) . . . . ?
C7 C5 O6 C2 -177.47(17) . . . . ?
N4 C5 C7 N8 179.2(2) . . . . ?
O6 C5 C7 N8 -2.5(3) . . . . ?
N4 C5 C7 C11 -2.4(3) . . . . ?
O6 C5 C7 C11 175.87(18) . . . . ?
C11 C7 N8 O9 0.1(2) . . . . ?
C5 C7 N8 O9 178.69(17) . . . . ?
C7 N8 O9 N10 -0.1(2) . . . . ?
N8 O9 N10 C11 0.0(2) . . . . ?
O9 N10 C11 N12 -178.97(19) . . . . ?
O9 N10 C11 C7 0.0(2) . . . . ?
N8 C7 C11 N10 -0.1(2) . . . . ?
C5 C7 C11 N10 -178.5(2) . . . . ?
N8 C7 C11 N12 179.05(17) . . . . ?
C5 C7 C11 N12 0.6(3) . . . . ?
N10 C11 N12 N13 -0.3(3) . . . . ?
C7 C11 N12 N13 -179.13(17) . . . . ?
C11 N12 N13 O14 -1.6(3) . . . . ?
C11 N12 N13 O15 178.02(16) . . . . ?

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
N1 H1A O1S 0.89(2) 1.89(2) 2.774(2) 177(2) 4_666
N1 H1B O15 0.86(2) 2.00(2) 2.821(3) 159(2) 3_766
N3 H3 N12 0.84(2) 2.21(2) 3.041(2) 170.7(19) 3_766
O1S H1S N10 0.84(3) 2.15(3) 2.901(2) 149(3) 3_656
O1S H2S O14 0.77(3) 2.11(3) 2.872(2) 172(3) 1_655

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.043


# start Validation Reply Form
_vrf_PLAT015_shrv320             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
_vrf_PLAT430_shrv320             
;
PROBLEM: Short Inter D...A Contact  N4     ..  N4      ..       2.67 Ang.  
RESPONSE: High density energetic materials often display close contacts.
;
# end Validation Reply Form

