# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shrv435
_database_code_depnum_ccdc_archive 'CCDC 1847117'
_audit_update_record             
;
2018-06-04 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_shrv435             
;
PROBLEM: Short Inter D...A Contact  O1       ..O21              2.84 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
# Added during the CSD deposition process: Monday 04 June 2018 03:32 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 N8 O8, 2(H4 N)'
_chemical_formula_sum            'C5 H8 N10 O8'
_chemical_formula_weight         336.21

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'

_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                   18.9552(14)
_cell_length_b                   11.1084(8)
_cell_length_c                   14.2841(18)
_cell_angle_alpha                90
_cell_angle_beta                 126.1840(10)
_cell_angle_gamma                90
_cell_volume                     2427.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6152
_cell_measurement_theta_min      2.341
_cell_measurement_theta_max      29.863

_exptl_crystal_description       block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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            16212
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.266
_diffrn_reflns_theta_max         29.970
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3432
_reflns_number_gt                2878
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0476P)²+1.5837P] 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         3432
_refine_ls_number_parameters     232
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O1 O 0.61317(6) 0.40708(8) 0.31300(7) 0.0262(2) Uani 1 1 d . . . . .
O2 O 0.55417(5) 0.47016(8) 0.13676(7) 0.02184(18) Uani 1 1 d . . . . .
N3 N 0.58846(6) 0.49264(9) 0.24111(8) 0.01744(19) Uani 1 1 d . . . . .
N4 N 0.60206(6) 0.60110(8) 0.28537(8) 0.01837(19) Uani 1 1 d . . . . .
C5 C 0.57691(7) 0.69590(10) 0.20994(9) 0.0163(2) Uani 1 1 d . . . . .
N6 N 0.53986(7) 0.69973(9) 0.09751(8) 0.0218(2) Uani 1 1 d . . . . .
O7 O 0.52868(6) 0.82308(8) 0.07034(7) 0.02381(19) Uani 1 1 d . . . . .
N8 N 0.55921(6) 0.89312(9) 0.16670(8) 0.0203(2) Uani 1 1 d . . . . .
C9 C 0.58898(7) 0.81756(10) 0.25213(9) 0.0167(2) Uani 1 1 d . . . . .
C10 C 0.62544(7) 0.86089(10) 0.36900(9) 0.0162(2) Uani 1 1 d . . . . .
N11 N 0.64516(7) 0.78854(9) 0.45350(8) 0.0206(2) Uani 1 1 d . . . . .
O12 O 0.67204(6) 0.86859(7) 0.54596(7) 0.02049(18) Uani 1 1 d . . . . .
C13 C 0.66542(7) 0.98060(9) 0.50481(9) 0.0163(2) Uani 1 1 d . . . . .
N14 N 0.63729(6) 0.98112(8) 0.39542(8) 0.01794(19) Uani 1 1 d . . . . .
C15 C 0.68910(7) 1.08333(9) 0.57795(9) 0.0169(2) Uani 1 1 d . . . . .
N16 N 0.73065(6) 1.07678(8) 0.69619(8) 0.01646(18) Uani 1 1 d . . . . .
O17 O 0.74309(6) 0.97363(7) 0.74015(7) 0.02179(18) Uani 1 1 d . . . . .
O18 O 0.75224(6) 1.16925(7) 0.75712(7) 0.02232(18) Uani 1 1 d . . . . .
N19 N 0.66937(6) 1.19970(8) 0.52533(8) 0.01808(19) Uani 1 1 d . . . . .
O20 O 0.72089(6) 1.28361(7) 0.57639(7) 0.0261(2) Uani 1 1 d . . . . .
O21 O 0.59929(6) 1.21026(8) 0.42763(7) 0.02430(19) Uani 1 1 d . . . . .
N22 N 0.63288(7) 0.52355(9) 0.50970(8) 0.0197(2) Uani 1 1 d D . . . .
H22A H 0.6747(9) 0.5048(14) 0.5841(9) 0.030 Uiso 1 1 d D U . . .
H22B H 0.6320(11) 0.4721(12) 0.4603(12) 0.030 Uiso 1 1 d D U . . .
H22C H 0.6350(10) 0.5989(9) 0.4903(13) 0.030 Uiso 1 1 d D U . . .
H22D H 0.5806(7) 0.5177(14) 0.4976(14) 0.030 Uiso 1 1 d D U . . .
N23 N 0.59939(7) 0.17807(9) 0.21593(9) 0.0211(2) Uani 1 1 d D . . . .
H23A H 0.5473(7) 0.1664(14) 0.1469(10) 0.032 Uiso 1 1 d D U . . .
H23B H 0.6026(10) 0.2508(10) 0.2469(13) 0.032 Uiso 1 1 d D U . . .
H23C H 0.6060(10) 0.1213(12) 0.2650(12) 0.032 Uiso 1 1 d D U . . .
H23D H 0.6430(8) 0.1732(14) 0.2081(14) 0.032 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.2686(12) . ?
O2 N3 1.2500(12) . ?
N3 N4 1.3135(13) . ?
N4 C5 1.3750(14) . ?
C5 N6 1.3200(14) . ?
C5 C9 1.4419(15) . ?
N6 O7 1.4057(13) . ?
O7 N8 1.3764(12) . ?
N8 C9 1.3034(14) . ?
C9 C10 1.4608(14) . ?
C10 N11 1.3076(14) . ?
C10 N14 1.3699(14) . ?
N11 O12 1.4141(12) . ?
O12 C13 1.3500(13) . ?
C13 N14 1.3198(14) . ?
C13 C15 1.4288(14) . ?
C15 N16 1.3812(13) . ?
C15 N19 1.4296(13) . ?
N16 O18 1.2488(12) . ?
N16 O17 1.2601(12) . ?
N19 O20 1.2302(12) . ?
N19 O21 1.2398(12) . ?
N22 H22A 0.898(9) . ?
N22 H22B 0.900(9) . ?
N22 H22C 0.890(9) . ?
N22 H22D 0.902(9) . ?
N23 H23A 0.903(9) . ?
N23 H23B 0.905(9) . ?
N23 H23C 0.895(9) . ?
N23 H23D 0.898(9) . ?

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
O2 N3 O1 119.94(9) . . ?
O2 N3 N4 124.98(10) . . ?
O1 N3 N4 115.08(9) . . ?
N3 N4 C5 116.53(9) . . ?
N6 C5 N4 131.86(10) . . ?
N6 C5 C9 108.51(9) . . ?
N4 C5 C9 119.62(9) . . ?
C5 N6 O7 104.63(9) . . ?
N8 O7 N6 111.66(8) . . ?
C9 N8 O7 105.44(9) . . ?
N8 C9 C5 109.76(9) . . ?
N8 C9 C10 120.60(10) . . ?
C5 C9 C10 129.62(10) . . ?
N11 C10 N14 115.71(9) . . ?
N11 C10 C9 122.48(10) . . ?
N14 C10 C9 121.74(10) . . ?
C10 N11 O12 102.98(8) . . ?
C13 O12 N11 106.46(8) . . ?
N14 C13 O12 112.85(9) . . ?
N14 C13 C15 126.52(10) . . ?
O12 C13 C15 120.62(9) . . ?
C13 N14 C10 101.99(9) . . ?
N16 C15 C13 123.94(9) . . ?
N16 C15 N19 118.28(9) . . ?
C13 C15 N19 117.77(9) . . ?
O18 N16 O17 120.84(9) . . ?
O18 N16 C15 121.64(9) . . ?
O17 N16 C15 117.46(9) . . ?
O20 N19 O21 122.93(9) . . ?
O20 N19 C15 120.24(9) . . ?
O21 N19 C15 116.83(9) . . ?
H22A N22 H22B 112.1(14) . . ?
H22A N22 H22C 114.6(15) . . ?
H22B N22 H22C 109.6(15) . . ?
H22A N22 H22D 108.1(14) . . ?
H22B N22 H22D 107.1(14) . . ?
H22C N22 H22D 104.7(14) . . ?
H23A N23 H23B 112.1(14) . . ?
H23A N23 H23C 108.1(14) . . ?
H23B N23 H23C 107.9(14) . . ?
H23A N23 H23D 110.4(14) . . ?
H23B N23 H23D 108.3(14) . . ?
H23C N23 H23D 109.9(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 N4 C5 -0.61(16) . . . . ?
O1 N3 N4 C5 179.28(10) . . . . ?
N3 N4 C5 N6 0.59(18) . . . . ?
N3 N4 C5 C9 179.35(9) . . . . ?
N4 C5 N6 O7 178.55(11) . . . . ?
C9 C5 N6 O7 -0.32(12) . . . . ?
C5 N6 O7 N8 0.09(12) . . . . ?
N6 O7 N8 C9 0.20(12) . . . . ?
O7 N8 C9 C5 -0.39(12) . . . . ?
O7 N8 C9 C10 -178.82(9) . . . . ?
N6 C5 C9 N8 0.47(13) . . . . ?
N4 C5 C9 N8 -178.56(10) . . . . ?
N6 C5 C9 C10 178.72(11) . . . . ?
N4 C5 C9 C10 -0.31(18) . . . . ?
N8 C9 C10 N11 170.64(11) . . . . ?
C5 C9 C10 N11 -7.45(18) . . . . ?
N8 C9 C10 N14 -6.24(16) . . . . ?
C5 C9 C10 N14 175.67(11) . . . . ?
N14 C10 N11 O12 0.77(13) . . . . ?
C9 C10 N11 O12 -176.29(9) . . . . ?
C10 N11 O12 C13 -0.33(11) . . . . ?
N11 O12 C13 N14 -0.19(12) . . . . ?
N11 O12 C13 C15 -179.18(10) . . . . ?
O12 C13 N14 C10 0.61(12) . . . . ?
C15 C13 N14 C10 179.52(11) . . . . ?
N11 C10 N14 C13 -0.88(13) . . . . ?
C9 C10 N14 C13 176.20(10) . . . . ?
N14 C13 C15 N16 -169.63(11) . . . . ?
O12 C13 C15 N16 9.20(17) . . . . ?
N14 C13 C15 N19 9.60(17) . . . . ?
O12 C13 C15 N19 -171.57(10) . . . . ?
C13 C15 N16 O18 177.98(10) . . . . ?
N19 C15 N16 O18 -1.25(16) . . . . ?
C13 C15 N16 O17 -4.71(16) . . . . ?
N19 C15 N16 O17 176.06(9) . . . . ?
N16 C15 N19 O20 37.48(15) . . . . ?
C13 C15 N19 O20 -141.79(11) . . . . ?
N16 C15 N19 O21 -142.82(10) . . . . ?
C13 C15 N19 O21 37.90(14) . . . . ?

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
N22 H22A N16 0.898(9) 2.657(11) 3.4436(14) 146.8(13) 4_646
N22 H22A O17 0.898(9) 2.057(9) 2.9467(13) 170.7(15) 4_646
N22 H22A O18 0.898(9) 2.586(14) 3.1450(13) 121.0(12) 4_646
N22 H22B O1 0.900(9) 2.047(10) 2.9100(13) 160.2(15) .
N22 H22C N11 0.890(9) 2.207(9) 3.0958(14) 176.5(14) .
N22 H22D O2 0.902(9) 2.168(12) 2.9226(13) 140.8(13) 2_655
N22 H22D O2 0.902(9) 2.323(14) 2.9535(13) 126.8(13) 6_566
N23 H23A O7 0.903(9) 2.538(12) 3.3005(14) 142.6(13) 5_665
N23 H23A O21 0.903(9) 2.366(13) 3.0654(14) 134.3(13) 2_645
N23 H23B O1 0.905(9) 1.929(9) 2.8345(13) 177.8(15) .
N23 H23B N3 0.905(9) 2.697(11) 3.5314(14) 153.7(13) .
N23 H23C N14 0.895(9) 2.223(9) 3.1146(14) 174.0(14) 1_545
N23 H23C O21 0.895(9) 2.596(15) 3.0462(14) 112.0(12) 1_545
N23 H23D O17 0.898(9) 2.334(13) 3.0441(14) 135.9(13) 6_565
N23 H23D O18 0.898(9) 2.468(14) 3.1074(14) 128.5(13) 7_666

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.055

