# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_x
_database_code_depnum_ccdc_archive 'CCDC 1566496'
_audit_update_record             
;
2018-04-18 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_audit_creation_date             2018-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C5 H2 N8 O4'
_chemical_formula_sum            'C5 H2 N8 O4'
_chemical_formula_weight         238.15
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   8.9130(18)
_cell_length_b                   14.057(3)
_cell_length_c                   6.5730(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     823.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      9
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            grass
_exptl_crystal_colour_primary    grass
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       strip
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1739
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_min         2.706
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1270
_reflns_number_total             1509
_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 V8.38A (?, 2016)'
_computing_data_collection       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 450 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.068
_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)+(0.0831P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.4848(4) 0.4882(2) 0.4807(6) 0.0326(8) Uani 1 1 d . . . . .
C1 C 0.3925(4) 0.5463(3) 0.5903(7) 0.0312(9) Uani 1 1 d . . . . .
O1 O 0.2238(4) 0.6709(3) 0.8011(6) 0.0664(12) Uani 1 1 d . . . . .
N2 N 0.5026(4) 0.4042(3) 0.5831(6) 0.0399(9) Uani 1 1 d . . . . .
C2 C 0.3574(5) 0.6401(3) 0.5148(7) 0.0316(9) Uani 1 1 d . . . . .
O2 O 0.2374(5) 0.7801(3) 0.5748(7) 0.0609(11) Uani 1 1 d . . . . .
O3 O 0.5737(4) 0.6706(3) -0.0918(5) 0.0456(9) Uani 1 1 d . . . . .
N3 N 0.4235(4) 0.4128(3) 0.7432(6) 0.0444(10) Uani 1 1 d . . . . .
C3 C 0.4083(4) 0.6708(3) 0.3240(6) 0.0310(9) Uani 1 1 d . . . . .
C4 C 0.5005(4) 0.6017(3) 0.2194(6) 0.0292(9) Uani 1 1 d . . . . .
O4 O 0.6484(3) 0.5220(2) 0.0082(5) 0.0418(8) Uani 1 1 d . . . . .
N4 N 0.3529(4) 0.4993(3) 0.7556(6) 0.0431(10) Uani 1 1 d . . . . .
N5 N 0.2675(4) 0.6998(3) 0.6357(6) 0.0419(10) Uani 1 1 d . . . . .
C5 C 0.5388(4) 0.5128(3) 0.2945(6) 0.0306(9) Uani 1 1 d . . . . .
N6 N 0.3836(4) 0.7521(3) 0.2340(6) 0.0421(10) Uani 1 1 d . . . . .
H6A H 0.329884 0.794819 0.293023 0.050 Uiso 1 1 calc R . . . .
H6B H 0.421077 0.763019 0.115711 0.050 Uiso 1 1 calc R . . . .
N7 N 0.5669(4) 0.6101(3) 0.0405(5) 0.0344(9) Uani 1 1 d . . . . .
N8 N 0.6258(4) 0.4636(3) 0.1738(6) 0.0385(9) 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
N1 C1 1.365(5) . ?
N1 N2 1.369(5) . ?
N1 C5 1.359(6) . ?
C1 C2 1.443(6) . ?
C1 N4 1.320(6) . ?
O1 N5 1.224(5) . ?
N2 N3 1.273(5) . ?
C2 C3 1.402(6) . ?
C2 N5 1.406(5) . ?
O2 N5 1.228(5) . ?
O3 N7 1.218(5) . ?
N3 N4 1.371(5) . ?
C3 C4 1.447(6) . ?
C3 N6 1.306(5) . ?
C4 C5 1.387(6) . ?
C4 N7 1.322(6) . ?
O4 N7 1.452(5) . ?
O4 N8 1.377(5) . ?
C5 N8 1.307(5) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?

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
C1 N1 N2 109.1(4) . . ?
C5 N1 C1 122.5(4) . . ?
C5 N1 N2 128.4(4) . . ?
N1 C1 C2 119.7(4) . . ?
N4 C1 N1 107.2(4) . . ?
N4 C1 C2 133.0(4) . . ?
N3 N2 N1 105.1(3) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 N5 120.4(4) . . ?
N5 C2 C1 118.3(4) . . ?
N2 N3 N4 112.9(4) . . ?
C2 C3 C4 113.7(4) . . ?
N6 C3 C2 128.4(4) . . ?
N6 C3 C4 117.9(4) . . ?
C5 C4 C3 125.2(4) . . ?
N7 C4 C3 128.1(4) . . ?
N7 C4 C5 106.7(4) . . ?
N8 O4 N7 108.6(3) . . ?
C1 N4 N3 105.8(4) . . ?
O1 N5 C2 119.0(4) . . ?
O1 N5 O2 121.7(4) . . ?
O2 N5 C2 119.3(4) . . ?
N1 C5 C4 117.5(4) . . ?
N8 C5 N1 128.5(4) . . ?
N8 C5 C4 114.0(4) . . ?
C3 N6 H6A 120.0 . . ?
C3 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
O3 N7 C4 136.1(4) . . ?
O3 N7 O4 117.8(3) . . ?
C4 N7 O4 106.1(3) . . ?
C5 N8 O4 104.6(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 C1 C2 C3 4.3(6) . . . . ?
N1 C1 C2 N5 -177.2(4) . . . . ?
N1 C1 N4 N3 0.3(4) . . . . ?
N1 N2 N3 N4 -0.3(5) . . . . ?
N1 C5 N8 O4 -178.8(4) . . . . ?
C1 N1 N2 N3 0.5(4) . . . . ?
C1 N1 C5 C4 2.0(6) . . . . ?
C1 N1 C5 N8 -179.1(4) . . . . ?
C1 C2 C3 C4 -2.0(6) . . . . ?
C1 C2 C3 N6 178.6(4) . . . . ?
C1 C2 N5 O1 1.0(6) . . . . ?
C1 C2 N5 O2 179.4(4) . . . . ?
N2 N1 C1 C2 179.4(3) . . . . ?
N2 N1 C1 N4 -0.5(5) . . . . ?
N2 N1 C5 C4 177.6(4) . . . . ?
N2 N1 C5 N8 -3.5(7) . . . . ?
N2 N3 N4 C1 0.0(5) . . . . ?
C2 C1 N4 N3 -179.6(4) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C2 C3 C4 N7 -178.6(4) . . . . ?
C3 C2 N5 O1 179.5(4) . . . . ?
C3 C2 N5 O2 -2.0(6) . . . . ?
C3 C4 C5 N1 0.4(6) . . . . ?
C3 C4 C5 N8 -178.7(4) . . . . ?
C3 C4 N7 O3 -1.6(8) . . . . ?
C3 C4 N7 O4 178.6(4) . . . . ?
C4 C5 N8 O4 0.1(5) . . . . ?
N4 C1 C2 C3 -175.9(4) . . . . ?
N4 C1 C2 N5 2.7(7) . . . . ?
N5 C2 C3 C4 179.5(4) . . . . ?
N5 C2 C3 N6 0.0(7) . . . . ?
C5 N1 C1 C2 -4.3(6) . . . . ?
C5 N1 C1 N4 175.9(4) . . . . ?
C5 N1 N2 N3 -175.6(4) . . . . ?
C5 C4 N7 O3 179.8(4) . . . . ?
C5 C4 N7 O4 0.0(4) . . . . ?
N6 C3 C4 C5 179.2(4) . . . . ?
N6 C3 C4 N7 0.9(6) . . . . ?
N7 C4 C5 N1 179.0(3) . . . . ?
N7 C4 C5 N8 -0.1(5) . . . . ?
N7 O4 N8 C5 -0.1(4) . . . . ?
N8 O4 N7 O3 -179.8(3) . . . . ?
N8 O4 N7 C4 0.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
