# Electronic Supplementary Material (ESI) for ChemComm.
# 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_zs1108b
_database_code_depnum_ccdc_archive 'CCDC 1542399'
_audit_update_record             
;
2017-04-05 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
3,4-Diaminofurazan/4-amino-3,5-dinitropyrazole
_chemical_name_common            DAF/ADNP
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H3 N5 O4, C2 H4 N4 O'
_chemical_formula_sum            'C5 H7 N9 O5'
_chemical_formula_weight         273.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.6432(2)
_cell_length_b                   13.5987(3)
_cell_length_c                   9.3093(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.897(8)
_cell_angle_gamma                90
_cell_volume                     1022.21(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    85(2)
_cell_measurement_reflns_used    7395
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      68.20

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.382
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_process_details   
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      85(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            15569
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         6.002
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_full        67.679
_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             1878
_reflns_number_gt                1808
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
    Cell determination at 295K
 8.697 x 13.663 x 9.612 x 90 x 110.68 x 90, Vol = 1068.73
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.3479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0102(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1878
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 0.71309(11) 0.15021(6) 0.37950(10) 0.0186(2) Uani 1 1 d . . . . .
O2 O -0.02864(11) 0.47045(7) 0.14917(11) 0.0260(3) Uani 1 1 d . . . . .
O3 O 0.01017(11) 0.31410(7) 0.12347(11) 0.0256(3) Uani 1 1 d . . . . .
O4 O 0.75878(11) 0.49431(6) 0.40883(10) 0.0208(2) Uani 1 1 d . . . . .
O5 O 0.60511(11) 0.62575(6) 0.38040(10) 0.0194(2) Uani 1 1 d . . . . .
N1 N 1.14200(14) 0.12915(9) 0.54714(13) 0.0200(3) Uani 1 1 d . . . . .
N2 N 1.01137(15) 0.33572(9) 0.47373(14) 0.0235(3) Uani 1 1 d . . . . .
H2B H 0.961(2) 0.3899(14) 0.4679(18) 0.024(4) Uiso 1 1 d . . . . .
H2A H 1.120(3) 0.3322(14) 0.542(2) 0.040(5) Uiso 1 1 d . . . . .
N3 N 0.85725(13) 0.09269(7) 0.43686(11) 0.0173(3) Uani 1 1 d . . . . .
N4 N 0.75643(13) 0.24990(7) 0.38974(12) 0.0184(3) Uani 1 1 d . . . . .
N5 N 0.24891(15) 0.59710(8) 0.26395(12) 0.0198(3) Uani 1 1 d . . . . .
H5B H 0.313(2) 0.6507(12) 0.2897(18) 0.023(4) Uiso 1 1 d . . . . .
H5A H 0.143(2) 0.6063(13) 0.2274(19) 0.028(4) Uiso 1 1 d . . . . .
N6 N 0.06127(13) 0.39740(8) 0.16390(12) 0.0189(3) Uani 1 1 d . . . . .
N7 N 0.33973(13) 0.33821(7) 0.25813(11) 0.0162(3) Uani 1 1 d . . . . .
N8 N 0.48796(13) 0.37819(7) 0.31339(11) 0.0154(2) Uani 1 1 d . . . . .
H8 H 0.581(2) 0.3394(14) 0.340(2) 0.033(4) Uiso 1 1 d . . . . .
N9 N 0.62289(13) 0.53560(7) 0.37309(11) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.98107(16) 0.15416(9) 0.47893(13) 0.0157(3) Uani 1 1 d . . . . .
C2 C 0.91766(15) 0.25339(9) 0.44906(13) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.31329(16) 0.50700(8) 0.27023(13) 0.0161(3) Uani 1 1 d . . . . .
C4 C 0.23464(15) 0.41426(9) 0.23145(13) 0.0159(3) Uani 1 1 d . . . . .
C5 C 0.47958(15) 0.47780(9) 0.32136(13) 0.0151(3) Uani 1 1 d . . . . .
H1B H 1.215(2) 0.1696(13) 0.5496(19) 0.030(4) Uiso 1 1 d . . . . .
H1A H 1.168(2) 0.0692(14) 0.5569(18) 0.028(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.4006(13) . ?
O1 N3 1.4053(13) . ?
O2 N6 1.2383(15) . ?
O3 N6 1.2253(14) . ?
O4 N9 1.2355(14) . ?
O5 N9 1.2404(14) . ?
N1 C1 1.3504(17) . ?
N1 H1B 0.83(2) . ?
N1 H1A 0.841(19) . ?
N2 C2 1.3526(17) . ?
N2 H2B 0.849(19) . ?
N2 H2A 0.93(2) . ?
N3 C1 1.3032(17) . ?
N4 C2 1.3039(17) . ?
N5 C3 1.3384(16) . ?
N5 H5B 0.897(18) . ?
N5 H5A 0.862(19) . ?
N6 C4 1.4217(16) . ?
N7 N8 1.3159(15) . ?
N7 C4 1.3399(16) . ?
N8 C5 1.3600(16) . ?
N8 H8 0.92(2) . ?
N9 C5 1.3995(16) . ?
C1 C2 1.4456(17) . ?
C3 C5 1.4007(17) . ?
C3 C4 1.4169(16) . ?

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
N4 O1 N3 109.48(8) . . ?
C1 N1 H1B 119.4(12) . . ?
C1 N1 H1A 118.8(12) . . ?
H1B N1 H1A 118.1(18) . . ?
C2 N2 H2B 116.3(12) . . ?
C2 N2 H2A 118.2(12) . . ?
H2B N2 H2A 117.5(17) . . ?
C1 N3 O1 106.20(9) . . ?
C2 N4 O1 106.48(10) . . ?
C3 N5 H5B 121.6(11) . . ?
C3 N5 H5A 121.0(12) . . ?
H5B N5 H5A 117.2(16) . . ?
O3 N6 O2 124.36(11) . . ?
O3 N6 C4 119.51(10) . . ?
O2 N6 C4 116.13(10) . . ?
N8 N7 C4 104.75(10) . . ?
N7 N8 C5 111.68(10) . . ?
N7 N8 H8 120.3(12) . . ?
C5 N8 H8 128.0(12) . . ?
O4 N9 O5 123.98(10) . . ?
O4 N9 C5 118.49(10) . . ?
O5 N9 C5 117.53(10) . . ?
N3 C1 N1 125.27(11) . . ?
N3 C1 C2 109.06(11) . . ?
N1 C1 C2 125.58(12) . . ?
N4 C2 N2 125.93(12) . . ?
N4 C2 C1 108.79(11) . . ?
N2 C2 C1 125.24(12) . . ?
N5 C3 C5 129.39(12) . . ?
N5 C3 C4 130.50(12) . . ?
C5 C3 C4 100.09(10) . . ?
N7 C4 C3 114.07(11) . . ?
N7 C4 N6 119.69(11) . . ?
C3 C4 N6 126.19(11) . . ?
N8 C5 N9 121.36(11) . . ?
N8 C5 C3 109.39(10) . . ?
N9 C5 C3 129.25(11) . . ?

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
N4 O1 N3 C1 -0.23(11) . . . . ?
N3 O1 N4 C2 0.32(12) . . . . ?
C4 N7 N8 C5 -0.46(12) . . . . ?
O1 N3 C1 N1 176.75(11) . . . . ?
O1 N3 C1 C2 0.06(12) . . . . ?
O1 N4 C2 N2 177.49(11) . . . . ?
O1 N4 C2 C1 -0.28(13) . . . . ?
N3 C1 C2 N4 0.15(13) . . . . ?
N1 C1 C2 N4 -176.54(11) . . . . ?
N3 C1 C2 N2 -177.64(11) . . . . ?
N1 C1 C2 N2 5.68(19) . . . . ?
N8 N7 C4 C3 -0.37(13) . . . . ?
N8 N7 C4 N6 177.21(10) . . . . ?
N5 C3 C4 N7 -177.60(12) . . . . ?
C5 C3 C4 N7 0.98(13) . . . . ?
N5 C3 C4 N6 5.0(2) . . . . ?
C5 C3 C4 N6 -176.41(11) . . . . ?
O3 N6 C4 N7 -3.76(17) . . . . ?
O2 N6 C4 N7 176.77(10) . . . . ?
O3 N6 C4 C3 173.49(11) . . . . ?
O2 N6 C4 C3 -5.97(17) . . . . ?
N7 N8 C5 N9 -178.32(10) . . . . ?
N7 N8 C5 C3 1.13(13) . . . . ?
O4 N9 C5 N8 1.50(16) . . . . ?
O5 N9 C5 N8 -178.39(10) . . . . ?
O4 N9 C5 C3 -177.83(11) . . . . ?
O5 N9 C5 C3 2.29(17) . . . . ?
N5 C3 C5 N8 177.40(12) . . . . ?
C4 C3 C5 N8 -1.20(12) . . . . ?
N5 C3 C5 N9 -3.2(2) . . . . ?
C4 C3 C5 N9 178.19(11) . . . . ?

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
N2 H2B O4 0.849(19) 2.164(19) 2.9735(15) 159.5(16) .
N2 H2A O5 0.93(2) 2.29(2) 3.1457(15) 152.1(16) 3_766
N5 H5B O3 0.897(18) 2.653(18) 3.5476(15) 175.8(14) 2
N5 H5B O5 0.897(18) 2.381(18) 2.9025(16) 117.2(13) .
N5 H5A O2 0.862(19) 2.320(18) 2.8345(15) 118.6(14) .
N8 H8 N4 0.92(2) 1.87(2) 2.7851(15) 174.5(18) .
N1 H1B O3 0.83(2) 2.41(2) 3.1006(15) 141.9(16) 4_766
N1 H1A O2 0.841(19) 2.513(18) 2.9853(15) 116.5(14) 4_766
N1 H1A N3 0.841(19) 2.215(19) 3.0204(16) 160.4(16) 3_756

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.060

_shelxl_version_number           2014/6

