# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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data_dm17170
_database_code_depnum_ccdc_archive 'CCDC 1567754'
_audit_update_record             
;
2017-08-09 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_audit_creation_date             2017-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        ABTOX
_chemical_formula_moiety         '0.5(C4 N16 O4), 2(H4 N)'
_chemical_formula_sum            'C2 H8 N10 O2'
_chemical_formula_weight         204.18
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   7.5982(12)
_cell_length_b                   7.5982(12)
_cell_length_c                   13.294(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     767.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1204
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.52
_cell_measurement_theta_min      3.06
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0865 before and 0.0608 after correction. The Ratio of minimum to maximum transmission is 0.8271. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.682
_diffrn_reflns_theta_min         3.065
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                986
_reflns_number_total             1189
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1189
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.0060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1068
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Restrained distances
 N9-H9_$1 = N8_$2-H8B_$3 = N8_$2-H8A_$3 = N10_$4-H10_$3
 0.82 with sigma of 0.02
2. Others
 Fixed Sof: N2(0.5) N3(0.5) N4(0.5) C1(0.5) N5(0.5) N6(0.5) N7(0.5) C2(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.7735(3) 0.7735(3) 0.34330(10) 0.0288(4) Uani 1 1 d . . . . .
N1 N 0.7752(3) 0.7754(3) 0.44276(12) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.7761(6) 0.6216(5) 0.4916(5) 0.0290(9) Uani 0.5 1 d . . . A 1
N3 N 0.7826(6) 0.6583(6) 0.5878(4) 0.0319(11) Uani 0.5 1 d . . . A 1
N4 N 0.7868(9) 0.8351(9) 0.6030(6) 0.0244(12) Uani 0.5 1 d . . . A 1
C1 C 0.7791(5) 0.9070(5) 0.5111(4) 0.0184(9) Uani 0.5 1 d . . . A 1
N8 N 0.5000 0.5000 0.7244(2) 0.0282(6) Uani 1 2 d DS T P . .
H8A H 0.560(7) 0.439(7) 0.687(3) 0.097(16) Uiso 1 1 d D . . . .
H8B H 0.566(6) 0.568(5) 0.760(2) 0.069(13) Uiso 1 1 d D . . . .
N9 N 1.0000 0.5000 0.7500 0.0282(9) Uani 1 4 d DS T P . .
H9 H 1.054(4) 0.566(4) 0.706(3) 0.042(9) Uiso 1 1 d D . . . .
N10 N 0.5000 1.0000 0.7500 0.0277(9) Uani 1 4 d DS T P . .
H10 H 0.564(4) 1.054(4) 0.705(3) 0.044(10) Uiso 1 1 d D . . . .
N5 N 0.7755(5) 1.3789(5) 0.5086(5) 0.0289(10) Uani 0.5 1 d . . . A 1
N6 N 0.7824(6) 1.3417(6) 0.4128(4) 0.0332(11) Uani 0.5 1 d . . . A 1
N7 N 0.7854(9) 1.1661(10) 0.3973(7) 0.0250(13) Uani 0.5 1 d . . . A 1
C2 C 0.7794(6) 1.0935(5) 0.4889(4) 0.0184(9) Uani 0.5 1 d . . . A 1


_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 N1 1.322(2) . ?
N1 N2 1.337(5) . ?
N1 C1 1.351(5) . ?
N1 N5 1.338(5) 4_756 ?
N1 C2 1.350(5) 4_756 ?
N2 N3 1.310(8) . ?
N2 N5 1.660(5) 4_756 ?
N2 N5 1.858(5) 1_545 ?
N2 C2 1.577(6) 4_756 ?
N3 N4 1.359(8) . ?
N3 N6 1.335(5) 4_756 ?
N3 N7 1.060(10) 4_756 ?
N3 C2 1.664(6) 4_756 ?
N4 C1 1.339(10) . ?
N4 N6 1.076(10) 4_756 ?
N4 N7 0.520(5) 4_756 ?
N4 C2 1.580(9) 4_756 ?
C1 N5 1.584(6) 4_756 ?
C1 N6 1.662(6) 4_756 ?
C1 N7 1.584(9) 4_756 ?
C1 C2 1.448(5) . ?
C1 C2 1.370(5) 4_756 ?
N8 H8A 0.82(2) . ?
N8 H8B 0.86(2) . ?
N9 H9 0.88(2) . ?
N10 H10 0.87(2) . ?
N5 N1 1.338(5) 3_576 ?
N5 N2 1.858(5) 1_565 ?
N5 N2 1.659(5) 3_576 ?
N5 C1 1.584(6) 3_576 ?
N5 N6 1.305(8) . ?
N6 N3 1.335(5) 3_576 ?
N6 N4 1.076(10) 3_576 ?
N6 C1 1.662(6) 3_576 ?
N6 N7 1.350(8) . ?
N7 N3 1.060(10) 3_576 ?
N7 N4 0.520(5) 3_576 ?
N7 C1 1.584(9) 3_576 ?
N7 C2 1.337(10) . ?
C2 N1 1.350(5) 3_576 ?
C2 N2 1.577(6) 3_576 ?
C2 N3 1.664(6) 3_576 ?
C2 N4 1.580(9) 3_576 ?
C2 C1 1.370(5) 3_576 ?

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
O1 N1 N2 118.4(3) . . ?
O1 N1 C1 132.9(3) . . ?
O1 N1 N5 118.4(3) . 4_756 ?
O1 N1 C2 132.9(3) . 4_756 ?
N2 N1 C1 108.7(4) . . ?
N2 N1 N5 76.7(3) . 4_756 ?
N2 N1 C2 71.9(3) . 4_756 ?
N5 N1 C1 72.2(3) 4_756 . ?
N5 N1 C2 108.7(4) 4_756 4_756 ?
C2 N1 C1 60.9(3) 4_756 . ?
N1 N2 N5 157.9(4) . 1_545 ?
N1 N2 N5 51.7(3) . 4_756 ?
N1 N2 C2 54.4(3) . 4_756 ?
N3 N2 N1 106.7(4) . . ?
N3 N2 N5 83.0(4) . 4_756 ?
N3 N2 N5 95.3(3) . 1_545 ?
N3 N2 C2 69.7(4) . 4_756 ?
N5 N2 N5 134.3(4) 4_756 1_545 ?
C2 N2 N5 137.4(3) 4_756 1_545 ?
C2 N2 N5 84.8(3) 4_756 4_756 ?
N2 N3 N4 110.9(6) . . ?
N2 N3 N6 96.8(5) . 4_756 ?
N2 N3 C2 62.7(3) . 4_756 ?
N4 N3 C2 62.0(4) . 4_756 ?
N6 N3 N4 47.1(4) 4_756 . ?
N6 N3 C2 90.4(4) 4_756 4_756 ?
N7 N3 N2 113.0(6) 4_756 . ?
N7 N3 N4 20.4(5) 4_756 . ?
N7 N3 N6 67.5(4) 4_756 4_756 ?
N7 N3 C2 53.3(5) 4_756 4_756 ?
N3 N4 C2 68.5(4) . 4_756 ?
C1 N4 N3 105.5(6) . . ?
C1 N4 C2 55.2(4) . 4_756 ?
N6 N4 N3 65.3(5) 4_756 . ?
N6 N4 C1 86.2(6) 4_756 . ?
N6 N4 C2 105.8(7) 4_756 4_756 ?
N7 N4 N3 45.3(17) 4_756 . ?
N7 N4 C1 109(2) 4_756 . ?
N7 N4 N6 111(2) 4_756 4_756 ?
N7 N4 C2 53.4(17) 4_756 4_756 ?
N1 C1 N5 53.5(3) . 4_756 ?
N1 C1 N6 88.6(3) . 4_756 ?
N1 C1 N7 95.2(4) . 4_756 ?
N1 C1 C2 59.5(3) . 4_756 ?
N1 C1 C2 126.0(4) . . ?
N4 C1 N1 108.2(4) . . ?
N4 C1 N5 85.8(5) . 4_756 ?
N4 C1 N6 40.2(4) . 4_756 ?
N4 C1 N7 18.1(4) . 4_756 ?
N4 C1 C2 71.3(4) . 4_756 ?
N4 C1 C2 125.8(5) . . ?
N5 C1 N6 47.3(3) 4_756 4_756 ?
N5 C1 N7 87.6(5) 4_756 4_756 ?
N7 C1 N6 49.1(4) 4_756 4_756 ?
C2 C1 N5 125.8(4) . 4_756 ?
C2 C1 N5 95.1(4) 4_756 4_756 ?
C2 C1 N6 89.2(4) 4_756 4_756 ?
C2 C1 N6 133.0(4) . 4_756 ?
C2 C1 N7 136.7(5) . 4_756 ?
C2 C1 N7 53.2(4) 4_756 4_756 ?
C2 C1 C2 133.8(5) 4_756 . ?
H8A N8 H8B 111(5) . . ?
N1 N5 N2 158.0(4) 3_576 1_565 ?
N1 N5 N2 51.6(3) 3_576 3_576 ?
N1 N5 C1 54.3(2) 3_576 3_576 ?
N2 N5 N2 134.9(4) 3_576 1_565 ?
C1 N5 N2 84.6(3) 3_576 3_576 ?
C1 N5 N2 137.0(3) 3_576 1_565 ?
N6 N5 N1 106.4(4) . 3_576 ?
N6 N5 N2 82.8(4) . 3_576 ?
N6 N5 N2 95.5(3) . 1_565 ?
N6 N5 C1 69.5(4) . 3_576 ?
N3 N6 C1 90.8(4) 3_576 3_576 ?
N3 N6 N7 46.5(4) 3_576 . ?
N4 N6 N3 67.6(4) 3_576 3_576 ?
N4 N6 C1 53.5(5) 3_576 3_576 ?
N4 N6 N5 113.7(6) 3_576 . ?
N4 N6 N7 21.1(4) 3_576 . ?
N5 N6 N3 97.5(5) . 3_576 ?
N5 N6 C1 63.2(3) . 3_576 ?
N5 N6 N7 111.3(6) . . ?
N7 N6 C1 62.4(4) . 3_576 ?
N3 N7 C1 106.9(7) 3_576 3_576 ?
N3 N7 N6 66.0(5) 3_576 . ?
N3 N7 C2 87.1(6) 3_576 . ?
N4 N7 N3 114(2) 3_576 3_576 ?
N4 N7 C1 53.2(16) 3_576 3_576 ?
N4 N7 N6 48.2(17) 3_576 . ?
N4 N7 C2 108.4(19) 3_576 . ?
N6 N7 C1 68.5(4) . 3_576 ?
C2 N7 C1 55.1(4) . 3_576 ?
C2 N7 N6 105.6(7) . . ?
N1 C2 N2 53.7(3) 3_576 3_576 ?
N1 C2 N3 89.0(3) 3_576 3_576 ?
N1 C2 N4 95.8(4) 3_576 3_576 ?
N1 C2 C1 59.6(3) 3_576 3_576 ?
N1 C2 C1 125.9(4) 3_576 . ?
N2 C2 N3 47.6(3) 3_576 3_576 ?
N2 C2 N4 88.3(5) 3_576 3_576 ?
N4 C2 N3 49.4(3) 3_576 3_576 ?
C1 C2 N2 125.5(4) . 3_576 ?
C1 C2 N2 95.4(3) 3_576 3_576 ?
C1 C2 N3 132.7(4) . 3_576 ?
C1 C2 N3 89.6(4) 3_576 3_576 ?
C1 C2 N4 53.4(4) 3_576 3_576 ?
C1 C2 N4 136.2(5) . 3_576 ?
C1 C2 C1 133.8(5) 3_576 . ?
N7 C2 N1 108.0(5) . 3_576 ?
N7 C2 N2 85.2(5) . 3_576 ?
N7 C2 N3 39.5(4) . 3_576 ?
N7 C2 N4 18.2(3) . 3_576 ?
N7 C2 C1 126.1(5) . . ?
N7 C2 C1 71.6(4) . 3_576 ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
