# 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_js1016ab
_database_code_depnum_ccdc_archive 'CCDC 1847183'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2016-10-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.10.10 svn.r3347 for OlexSys, GUI svn.r5252)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(Ag4 H24 N8), 0.5(C4 N8 O16)'
_chemical_formula_sum            'C2 H12 Ag2 N8 O8'
_chemical_formula_weight         491.94
_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'
Ag Ag -0.8971 1.1015 '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           87
_space_group_name_H-M_alt        'I 4/m'
_space_group_name_Hall           '-I 4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   11.6936(9)
_cell_length_b                   11.6936(9)
_cell_length_c                   8.8330(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1207.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8881
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.459
_exptl_absorpt_coefficient_mu    3.301
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0666 before and 0.0395 after correction. The Ratio of minimum to maximum transmission is 0.8205. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.088
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9946
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.180
_diffrn_reflns_theta_min         2.463
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                584
_reflns_number_total             586
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.422
_refine_diff_density_min         -2.225
_refine_diff_density_rms         0.399
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         586
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0663
_refine_ls_restrained_S_all      1.196
_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)+(0.1417P)²+59.2594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2378
_refine_ls_wR_factor_ref         0.2378
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N4) = Uanis(N3)
Uanis(N2) = Uanis(N3)
Uanis(N1) = Uanis(N4)
3. Others
 Fixed Sof: Ag2(0.25) N3(0.5) H3A(0.5) H3B(0.5) H3C(0.5) N4(0.5) H4A(0.5)
 H4B(0.5) H4C(0.5) O1(0.5) O2(0.5) O3(0.5) O4(0.5) N1(0.5) N2(0.5)
4.a Riding coordinates:
 N4(H4A,H4B,H4C)
4.b Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Ag1 Ag 0.5000 0.5000 0.68967(18) 0.0213(7) Uani 1 4 d S T P . .
Ag2 Ag 0.5000(2) 0.3578(2) 1.0000 0.0208(8) Uani 0.5 2 d S T P A .
N3 N 0.6271(17) 0.3723(17) 0.684(2) 0.021(2) Uani 0.5 1 d . . . A 1
H3A H 0.6415 0.3525 0.5863 0.025 Uiso 0.5 1 calc GR . . A 1
H3B H 0.6025 0.3099 0.7361 0.025 Uiso 0.5 1 calc GR . . A 1
H3C H 0.6923 0.3995 0.7273 0.025 Uiso 0.5 1 calc GR . . A 1
N4 N 0.6617(15) 0.3380(16) 0.910(2) 0.021(2) Uani 0.5 1 d . . . A 2
H4A H 0.7133 0.3315 0.9862 0.025 Uiso 0.5 1 d R . . A 2
H4B H 0.6794 0.3998 0.8516 0.025 Uiso 0.5 1 d R . . A 2
H4C H 0.6636 0.2738 0.8516 0.025 Uiso 0.5 1 d R . . A 2
O1 O 0.6546(12) 0.0556(14) 0.6498(18) 0.021(3) Uani 0.5 1 d . . . B 1
O2 O 0.5920(14) 0.2235(12) 0.5856(19) 0.026(4) Uani 0.5 1 d . . . B 1
O3 O 0.3451(12) 0.0555(14) 0.3507(18) 0.022(3) Uani 0.5 1 d . . . B 1
O4 O 0.4079(14) 0.2233(12) 0.4143(19) 0.026(4) Uani 0.5 1 d . . . B 1
N1 N 0.5827(15) 0.1193(17) 0.584(2) 0.021(2) Uani 0.5 1 d . . . B 1
N2 N 0.4173(15) 0.1191(17) 0.417(2) 0.021(2) Uani 0.5 1 d . . . B 1
C1 C 0.4998(12) 0.0602(14) 0.5000 0.015(3) Uani 1 2 d S T P B 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
Ag1 Ag1 3.351(3) 9_666 ?
Ag1 Ag2 3.2063(19) . ?
Ag1 Ag2 3.2064(19) 2_655 ?
Ag1 Ag2 3.2064(19) 9_667 ?
Ag1 Ag2 3.2063(19) 10_567 ?
Ag1 N3 2.11(2) 2_655 ?
Ag1 N3 2.11(2) 3_665 ?
Ag1 N3 2.11(2) . ?
Ag1 N3 2.11(2) 4_565 ?
Ag2 Ag1 3.2064(19) 9_667 ?
Ag2 Ag2 2.352(3) 10_567 ?
Ag2 Ag2 2.352(3) 2_655 ?
Ag2 Ag2 3.327(5) 9_667 ?
Ag2 N4 2.068(18) 10_567 ?
Ag2 N4 2.065(18) . ?
Ag2 N4 2.068(18) 4_565 ?
Ag2 N4 2.065(18) 11_557 ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N4 Ag2 2.068(18) 2_655 ?
N4 N4 1.60(4) 11_557 ?
N4 H4A 0.9101 . ?
N4 H4B 0.9097 . ?
N4 H4C 0.9097 . ?
O1 O3 1.30(2) 9_656 ?
O1 N1 1.27(2) . ?
O2 O2 1.51(3) 11_556 ?
O2 N1 1.22(3) . ?
O3 O1 1.30(2) 9_656 ?
O3 N2 1.27(2) . ?
O4 O4 1.51(3) 11_556 ?
O4 N2 1.22(2) . ?
N1 N1 1.48(4) 11_556 ?
N1 C1 1.40(2) . ?
N2 N2 1.47(4) 11_556 ?
N2 C1 1.40(2) . ?
C1 N1 1.40(2) 11_556 ?
C1 N2 1.40(2) 11_556 ?
C1 C1 1.41(3) 9_656 ?

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
Ag2 Ag1 Ag1 148.75(4) 2_655 9_666 ?
Ag2 Ag1 Ag1 148.75(4) 10_567 9_666 ?
Ag2 Ag1 Ag1 148.75(4) . 9_666 ?
Ag2 Ag1 Ag1 148.75(4) 9_667 9_666 ?
Ag2 Ag1 Ag2 62.50(8) 2_655 10_567 ?
Ag2 Ag1 Ag2 43.04(5) . 10_567 ?
Ag2 Ag1 Ag2 43.04(5) 9_667 10_567 ?
Ag2 Ag1 Ag2 43.04(5) . 2_655 ?
Ag2 Ag1 Ag2 62.50(8) . 9_667 ?
Ag2 Ag1 Ag2 43.04(5) 2_655 9_667 ?
N3 Ag1 Ag1 88.7(5) 4_565 9_666 ?
N3 Ag1 Ag1 88.7(5) 3_665 9_666 ?
N3 Ag1 Ag1 88.7(5) 2_655 9_666 ?
N3 Ag1 Ag1 88.7(5) . 9_666 ?
N3 Ag1 Ag2 112.8(5) 2_655 10_567 ?
N3 Ag1 Ag2 69.7(5) 3_665 9_667 ?
N3 Ag1 Ag2 69.7(5) 4_565 10_567 ?
N3 Ag1 Ag2 69.8(5) 4_565 . ?
N3 Ag1 Ag2 112.8(5) . 9_667 ?
N3 Ag1 Ag2 69.8(5) 3_665 10_567 ?
N3 Ag1 Ag2 69.8(5) . 2_655 ?
N3 Ag1 Ag2 112.8(5) 3_665 . ?
N3 Ag1 Ag2 112.7(5) 4_565 9_667 ?
N3 Ag1 Ag2 112.7(5) 3_665 2_655 ?
N3 Ag1 Ag2 112.7(5) 2_655 . ?
N3 Ag1 Ag2 112.8(5) 4_565 2_655 ?
N3 Ag1 Ag2 69.7(5) . . ?
N3 Ag1 Ag2 112.7(5) . 10_567 ?
N3 Ag1 Ag2 69.7(5) 2_655 2_655 ?
N3 Ag1 Ag2 69.8(5) 2_655 9_667 ?
N3 Ag1 N3 177.3(10) 3_665 . ?
N3 Ag1 N3 89.97(3) 4_565 . ?
N3 Ag1 N3 89.97(3) 2_655 3_665 ?
N3 Ag1 N3 89.97(3) 2_655 . ?
N3 Ag1 N3 89.97(3) 4_565 3_665 ?
N3 Ag1 N3 177.3(10) 4_565 2_655 ?
Ag1 Ag2 Ag1 117.50(8) . 9_667 ?
Ag1 Ag2 Ag2 58.75(4) 9_667 9_667 ?
Ag1 Ag2 Ag2 58.75(4) . 9_667 ?
Ag2 Ag2 Ag1 68.48(3) 10_567 9_667 ?
Ag2 Ag2 Ag1 68.48(3) 2_655 . ?
Ag2 Ag2 Ag1 68.48(3) 2_655 9_667 ?
Ag2 Ag2 Ag1 68.48(3) 10_567 . ?
Ag2 Ag2 Ag2 45.0 2_655 9_667 ?
Ag2 Ag2 Ag2 45.0 10_567 9_667 ?
Ag2 Ag2 Ag2 90.0 2_655 10_567 ?
N4 Ag2 Ag1 112.9(5) . 9_667 ?
N4 Ag2 Ag1 74.2(5) . . ?
N4 Ag2 Ag1 112.8(5) 4_565 9_667 ?
N4 Ag2 Ag1 112.8(5) 10_567 . ?
N4 Ag2 Ag1 74.1(5) 4_565 . ?
N4 Ag2 Ag1 74.1(5) 10_567 9_667 ?
N4 Ag2 Ag1 74.2(5) 11_557 9_667 ?
N4 Ag2 Ag1 112.9(5) 11_557 . ?
N4 Ag2 Ag2 55.4(5) . 2_655 ?
N4 Ag2 Ag2 136.6(5) . 10_567 ?
N4 Ag2 Ag2 136.5(5) 10_567 2_655 ?
N4 Ag2 Ag2 96.4(5) 11_557 9_667 ?
N4 Ag2 Ag2 55.3(5) 10_567 10_567 ?
N4 Ag2 Ag2 55.3(5) 4_565 10_567 ?
N4 Ag2 Ag2 96.3(5) 4_565 9_667 ?
N4 Ag2 Ag2 55.4(5) 11_557 2_655 ?
N4 Ag2 Ag2 136.6(5) 11_557 10_567 ?
N4 Ag2 Ag2 96.3(5) 10_567 9_667 ?
N4 Ag2 Ag2 96.4(5) . 9_667 ?
N4 Ag2 Ag2 136.5(5) 4_565 2_655 ?
N4 Ag2 N4 132.6(9) 11_557 10_567 ?
N4 Ag2 N4 45.5(10) . 11_557 ?
N4 Ag2 N4 167.3(6) . 10_567 ?
N4 Ag2 N4 45.4(10) 4_565 10_567 ?
N4 Ag2 N4 132.6(9) . 4_565 ?
N4 Ag2 N4 167.3(6) 11_557 4_565 ?
Ag1 N3 H3A 109.5 . . ?
Ag1 N3 H3B 109.5 . . ?
Ag1 N3 H3C 109.5 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
Ag2 N4 Ag2 69.4(6) . 2_655 ?
Ag2 N4 H4A 82.1 2_655 . ?
Ag2 N4 H4A 109.2 . . ?
Ag2 N4 H4B 109.8 . . ?
Ag2 N4 H4B 61.0 2_655 . ?
Ag2 N4 H4C 109.4 . . ?
Ag2 N4 H4C 167.6 2_655 . ?
N4 N4 Ag2 67.3(5) 11_557 2_655 ?
N4 N4 Ag2 67.3(5) 11_557 . ?
N4 N4 H4A 42.0 11_557 . ?
N4 N4 H4B 124.3 11_557 . ?
N4 N4 H4C 124.3 11_557 . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
N1 O1 O3 126.0(16) . 9_656 ?
N1 O2 O2 89.3(12) . 11_556 ?
N2 O3 O1 125.9(16) . 9_656 ?
N2 O4 O4 89.1(12) . 11_556 ?
O1 N1 N1 117.4(11) . 11_556 ?
O1 N1 C1 114.4(18) . . ?
O2 N1 O1 121.4(19) . . ?
O2 N1 N1 90.7(12) . 11_556 ?
O2 N1 C1 124.0(18) . . ?
C1 N1 N1 58.1(8) . 11_556 ?
O3 N2 N2 117.4(11) . 11_556 ?
O3 N2 C1 114.5(18) . . ?
O4 N2 O3 121.1(19) . . ?
O4 N2 N2 90.9(12) . 11_556 ?
O4 N2 C1 124.2(18) . . ?
C1 N2 N2 58.1(8) . 11_556 ?
N1 C1 N1 63.9(16) 11_556 . ?
N1 C1 C1 119.4(15) 11_556 9_656 ?
N1 C1 C1 119.4(15) . 9_656 ?
N2 C1 N1 87.4(12) . 11_556 ?
N2 C1 N1 120.9(16) . . ?
N2 C1 N1 120.9(16) 11_556 11_556 ?
N2 C1 N1 87.4(12) 11_556 . ?
N2 C1 N2 63.7(16) . 11_556 ?
N2 C1 C1 119.7(15) 11_556 9_656 ?
N2 C1 C1 119.7(15) . 9_656 ?

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
N3 H3A O2 0.91 2.22 2.98(3) 140.9 11_556
N3 H3A O4 0.91 2.29 2.98(3) 133.3 2_655
N3 H3B O3 0.91 2.15 3.05(2) 175.3 8
N3 H3C O1 0.91 2.16 3.06(2) 172.3 13_656

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
O1 O3 N2 O4 -177.7(18) 9_656 . . . ?
O1 O3 N2 N2 -68(2) 9_656 . . 11_556 ?
O1 O3 N2 C1 -3(3) 9_656 . . . ?
O1 N1 C1 N1 -108.2(15) . . . 11_556 ?
O1 N1 C1 N2 125.3(17) . . . 11_556 ?
O1 N1 C1 N2 -177.6(15) . . . . ?
O1 N1 C1 C1 2(2) . . . 9_656 ?
O2 O2 N1 O1 123.1(18) 11_556 . . . ?
O2 O2 N1 N1 -0.001(3) 11_556 . . 11_556 ?
O2 O2 N1 C1 -51.0(16) 11_556 . . . ?
O2 N1 C1 N1 66(2) . . . 11_556 ?
O2 N1 C1 N2 -60(2) . . . 11_556 ?
O2 N1 C1 N2 -3(2) . . . . ?
O2 N1 C1 C1 176.8(16) . . . 9_656 ?
O3 O1 N1 O2 -177.0(18) 9_656 . . . ?
O3 O1 N1 N1 -68(2) 9_656 . . 11_556 ?
O3 O1 N1 C1 -2(3) 9_656 . . . ?
O3 N2 C1 N1 125.3(17) . . . 11_556 ?
O3 N2 C1 N1 -177.5(15) . . . . ?
O3 N2 C1 N2 -108.2(14) . . . 11_556 ?
O3 N2 C1 C1 3(2) . . . 9_656 ?
O4 O4 N2 O3 123.2(17) 11_556 . . . ?
O4 O4 N2 N2 -0.001(4) 11_556 . . 11_556 ?
O4 O4 N2 C1 -51.1(16) 11_556 . . . ?
O4 N2 C1 N1 -60(2) . . . 11_556 ?
O4 N2 C1 N1 -3(2) . . . . ?
O4 N2 C1 N2 66(2) . . . 11_556 ?
O4 N2 C1 C1 177.2(16) . . . 9_656 ?
N1 N1 C1 N2 -126.5(12) 11_556 . . 11_556 ?
N1 N1 C1 N2 -69.4(12) 11_556 . . . ?
N1 N1 C1 C1 110.5(14) 11_556 . . 9_656 ?
N2 N2 C1 N1 -69.3(12) 11_556 . . . ?
N2 N2 C1 N1 -126.6(12) 11_556 . . 11_556 ?
N2 N2 C1 C1 110.8(14) 11_556 . . 9_656 ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id YP-052
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_js1116a
_database_code_depnum_ccdc_archive 'CCDC 1847185'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2016-11-22
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H2 N3 O5, H7 N2 O2'
_chemical_formula_sum            'C2 H9 N5 O7'
_chemical_formula_weight         215.14
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7131(15)
_cell_length_b                   9.097(4)
_cell_length_c                   12.626(5)
_cell_angle_alpha                108.745(7)
_cell_angle_beta                 96.500(5)
_cell_angle_gamma                98.409(5)
_cell_volume                     393.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3229
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0536 before and 0.0437 after correction. The Ratio of minimum to maximum transmission is 0.9346. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             224
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.082
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6578
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.327
_diffrn_reflns_theta_min         1.729
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1169
_reflns_number_total             1451
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.118
_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)+(0.0683P)²+0.0361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1123
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the Hydrogen atom on the oxygen atom which was found by difference Fourier methods and refined isotropically.'
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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 0.7822(4) 0.32470(17) -0.08519(11) 0.0259(4) Uani 1 1 d . . . . .
O2 O 0.9204(4) 0.54836(15) 0.24886(11) 0.0283(4) Uani 1 1 d . . . . .
O3 O 0.6778(4) 0.46389(15) 0.37200(10) 0.0275(4) Uani 1 1 d . . . . .
O4 O 0.2051(4) 0.20491(16) 0.29288(11) 0.0295(4) Uani 1 1 d . . . . .
O5 O 0.2132(5) 0.05827(17) 0.12122(12) 0.0433(5) Uani 1 1 d . . . . .
N1 N 0.7923(4) 0.38219(18) 0.03313(12) 0.0218(4) Uani 1 1 d . . . . .
N2 N 0.7146(4) 0.44358(17) 0.27120(12) 0.0203(4) Uani 1 1 d . . . . .
N3 N 0.3158(4) 0.18609(18) 0.20087(13) 0.0230(4) Uani 1 1 d . . . . .
C1 C 0.5985(5) 0.2815(2) 0.06519(16) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.5495(5) 0.3079(2) 0.18133(15) 0.0193(4) Uani 1 1 d . . . . .
H1 H 0.906(7) 0.395(3) -0.095(2) 0.039(7) Uiso 1 1 d . . . . .
H1A H 0.474(6) 0.180(3) 0.0116(18) 0.028(5) Uiso 1 1 d . . . . .
O6 O 0.1264(4) 0.85179(15) 0.50011(11) 0.0266(4) Uani 1 1 d . . . . .
O7 O 0.4352(4) 1.08435(16) 0.66419(12) 0.0308(4) Uani 1 1 d . . . . .
N4 N 0.3525(5) 0.73715(19) 0.48276(15) 0.0229(4) Uani 1 1 d . . . . .
N5 N 0.1838(5) 1.1233(2) 0.73842(16) 0.0262(4) Uani 1 1 d . . . . .
H4A H 0.595(8) 0.776(3) 0.475(2) 0.046(7) Uiso 1 1 d . . . . .
H4B H 0.250(8) 0.652(4) 0.416(3) 0.068(9) Uiso 1 1 d . . . . .
H4C H 0.365(7) 0.699(3) 0.539(2) 0.044(7) Uiso 1 1 d . . . . .
H5A H 0.302(8) 1.216(3) 0.800(2) 0.053(7) Uiso 1 1 d . . . . .
H5B H -0.016(9) 1.138(3) 0.705(2) 0.063(9) Uiso 1 1 d . . . . .
H5C H 0.112(7) 1.050(3) 0.761(2) 0.045(8) Uiso 1 1 d . . . . .
H6 H 0.277(9) 0.965(4) 0.583(3) 0.085(10) 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 N1 1.409(2) . ?
O1 H1 0.78(3) . ?
O2 N2 1.2571(19) . ?
O3 N2 1.252(2) . ?
O4 N3 1.244(2) . ?
O5 N3 1.241(2) . ?
N1 C1 1.277(2) . ?
N2 C2 1.381(2) . ?
N3 C2 1.409(2) . ?
C1 C2 1.445(3) . ?
C1 H1A 0.96(2) . ?
O6 N4 1.411(2) . ?
O6 H6 1.22(3) . ?
O7 N5 1.399(2) . ?
O7 H6 1.24(3) . ?
N4 H4A 0.95(3) . ?
N4 H4B 0.94(3) . ?
N4 H4C 0.89(3) . ?
N5 H5A 0.95(3) . ?
N5 H5B 0.86(3) . ?
N5 H5C 0.83(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
N1 O1 H1 102.5(18) . . ?
C1 N1 O1 111.18(15) . . ?
O2 N2 C2 116.95(15) . . ?
O3 N2 O2 119.55(14) . . ?
O3 N2 C2 123.46(15) . . ?
O4 N3 C2 122.20(15) . . ?
O5 N3 O4 120.27(15) . . ?
O5 N3 C2 117.50(15) . . ?
N1 C1 C2 124.06(17) . . ?
N1 C1 H1A 120.9(12) . . ?
C2 C1 H1A 115.1(12) . . ?
N2 C2 N3 119.67(15) . . ?
N2 C2 C1 123.88(16) . . ?
N3 C2 C1 116.45(15) . . ?
N4 O6 H6 108.1(16) . . ?
N5 O7 H6 107.3(15) . . ?
O6 N4 H4A 113.3(15) . . ?
O6 N4 H4B 109.6(18) . . ?
O6 N4 H4C 110.8(16) . . ?
H4A N4 H4B 107(2) . . ?
H4A N4 H4C 109(2) . . ?
H4B N4 H4C 107(2) . . ?
O7 N5 H5A 107.9(16) . . ?
O7 N5 H5B 111.4(19) . . ?
O7 N5 H5C 111.7(17) . . ?
H5A N5 H5B 111(3) . . ?
H5A N5 H5C 111(2) . . ?
H5B N5 H5C 104(3) . . ?

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
O1 H1 N1 0.78(3) 2.02(3) 2.728(2) 149(2) 2_765
N4 H4A O6 0.95(3) 1.95(3) 2.868(2) 164(2) 1_655
N5 H5A O1 0.95(3) 2.06(3) 2.884(2) 145(2) 1_566
N5 H5B O7 0.86(3) 1.99(3) 2.764(3) 149(3) 1_455
O6 H6 O7 1.22(3) 1.24(3) 2.4531(19) 177(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
O1 N1 C1 C2 -178.76(15) . . . . ?
O2 N2 C2 N3 180.00(14) . . . . ?
O2 N2 C2 C1 -0.5(2) . . . . ?
O3 N2 C2 N3 2.3(3) . . . . ?
O3 N2 C2 C1 -178.21(16) . . . . ?
O4 N3 C2 N2 11.4(2) . . . . ?
O4 N3 C2 C1 -168.17(16) . . . . ?
O5 N3 C2 N2 -170.51(17) . . . . ?
O5 N3 C2 C1 9.9(2) . . . . ?
N1 C1 C2 N2 -1.7(3) . . . . ?
N1 C1 C2 N3 177.86(16) . . . . ?

_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id YP-081
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_js418a
_database_code_depnum_ccdc_archive 'CCDC 1847184'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2018-04-11
_audit_creation_method           
;
Olex2 1.2-alpha
(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         '2(C2 H2 N3 O5), H4 N O, H3 N O, H4 N'
_chemical_formula_sum            'C4 H15 N9 O12'
_chemical_formula_weight         381.25
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1131(10)
_cell_length_b                   8.6292(10)
_cell_length_c                   11.1334(13)
_cell_angle_alpha                106.9700(10)
_cell_angle_beta                 93.5300(10)
_cell_angle_gamma                105.5540(10)
_cell_volume                     709.89(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3270
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0451 before and 0.0368 after correction. The Ratio of minimum to maximum transmission is 0.9216. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             396
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.186
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5829
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.388
_diffrn_reflns_theta_min         1.935
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2144
_reflns_number_total             2596
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.069
_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     286
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.078
_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)+(0.0929P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1369
_refine_special_details          ?
_olex2_refinement_description    
;
;
_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 0.86755(19) 0.69153(18) 0.64235(14) 0.0244(4) Uani 1 1 d . . . . .
H1 H 0.802(3) 0.605(3) 0.577(3) 0.042(7) Uiso 1 1 d . . . . .
O2 O 0.78595(18) 1.06522(18) 0.51819(13) 0.0252(4) Uani 1 1 d . . . . .
O3 O 0.92613(19) 1.33264(17) 0.59636(14) 0.0268(4) Uani 1 1 d . . . . .
O4 O 1.14835(18) 1.42253(17) 0.79302(13) 0.0240(4) Uani 1 1 d . . . . .
O5 O 1.2082(2) 1.22453(19) 0.85160(15) 0.0343(4) Uani 1 1 d . . . . .
N1 N 0.8561(2) 0.8361(2) 0.61018(16) 0.0206(4) Uani 1 1 d . . . . .
N2 N 0.9012(2) 1.1835(2) 0.59762(15) 0.0197(4) Uani 1 1 d . . . . .
N3 N 1.1228(2) 1.2688(2) 0.77880(16) 0.0206(4) Uani 1 1 d . . . . .
C1 C 0.9680(3) 0.9687(3) 0.68595(19) 0.0197(4) Uani 1 1 d . . . . .
H1A H 1.037(3) 0.962(3) 0.747(2) 0.027(6) Uiso 1 1 d . . . . .
C2 C 0.9968(2) 1.1407(2) 0.68405(18) 0.0188(4) Uani 1 1 d . . . . .
O6 O 0.46684(19) 0.63311(19) 0.93216(14) 0.0254(4) Uani 1 1 d . . . . .
H6 H 0.374(3) 0.547(3) 0.885(2) 0.032(7) Uiso 1 1 d . . . . .
O7 O 0.4849(2) 0.93513(19) 0.71349(14) 0.0315(4) Uani 1 1 d . . . . .
O8 O 0.64865(18) 1.19308(17) 0.76056(13) 0.0247(4) Uani 1 1 d . . . . .
O9 O 0.88452(18) 1.29828(18) 0.95353(14) 0.0255(4) Uani 1 1 d . . . . .
O10 O 0.8694(2) 1.1428(2) 1.07439(16) 0.0449(5) Uani 1 1 d . . . . .
N4 N 0.4837(2) 0.7545(2) 0.86743(16) 0.0218(4) Uani 1 1 d . . . . .
N5 N 0.6016(2) 1.0575(2) 0.78586(16) 0.0200(4) Uani 1 1 d . . . . .
N6 N 0.8147(2) 1.1646(2) 0.97547(16) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.6140(3) 0.8831(3) 0.92700(19) 0.0219(5) Uani 1 1 d . . . . .
H3 H 0.683(3) 0.884(3) 1.000(2) 0.027(6) Uiso 1 1 d . . . . .
C4 C 0.6758(2) 1.0351(2) 0.89318(18) 0.0185(4) Uani 1 1 d . . . . .
O11 O 0.5292(2) 0.60584(19) 0.33546(13) 0.0274(4) Uani 1 1 d . . . . .
H11 H 0.579(4) 0.551(3) 0.378(2) 0.041(7) Uiso 1 1 d . . . . .
N7 N 0.5285(2) 0.7466(2) 0.44043(16) 0.0207(4) Uani 1 1 d . . . . .
H7A H 0.645(4) 0.808(3) 0.490(2) 0.043(7) Uiso 1 1 d . . . . .
H7B H 0.483(3) 0.813(3) 0.398(2) 0.032(6) Uiso 1 1 d . . . . .
H7C H 0.450(3) 0.700(3) 0.494(2) 0.040(7) Uiso 1 1 d . . . . .
O12 O 0.32001(17) 0.55498(16) 0.55716(12) 0.0210(3) Uani 1 1 d . . . . .
N8 N 0.2184(2) 0.6340(2) 0.63861(17) 0.0205(4) Uani 1 1 d . . . . .
H8A H 0.156(3) 0.682(3) 0.594(2) 0.027(6) Uiso 1 1 d . . . . .
H8B H 0.135(3) 0.551(3) 0.660(2) 0.035(7) Uiso 1 1 d . . . . .
H8C H 0.294(3) 0.710(3) 0.708(2) 0.030(6) Uiso 1 1 d . . . . .
N9 N 0.7885(3) 0.5515(2) 0.86412(19) 0.0257(4) Uani 1 1 d . . . . .
H9A H 0.780(4) 0.434(4) 0.845(3) 0.055(9) Uiso 1 1 d . . . . .
H9B H 0.703(5) 0.574(4) 0.902(3) 0.084(12) Uiso 1 1 d . . . . .
H9C H 0.893(5) 0.614(5) 0.920(3) 0.079(11) Uiso 1 1 d . . . . .
H9D H 0.791(4) 0.586(4) 0.790(3) 0.060(9) 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 H1 0.89(3) . ?
O1 N1 1.418(2) . ?
O2 N2 1.248(2) . ?
O3 N2 1.252(2) . ?
O4 N3 1.247(2) . ?
O5 N3 1.240(2) . ?
N1 C1 1.277(3) . ?
N2 C2 1.391(3) . ?
N3 C2 1.400(3) . ?
C1 H1A 0.88(3) . ?
C1 C2 1.446(3) . ?
O6 H6 0.91(3) . ?
O6 N4 1.418(2) . ?
O7 N5 1.238(2) . ?
O8 N5 1.249(2) . ?
O9 N6 1.242(2) . ?
O10 N6 1.245(2) . ?
N4 C3 1.282(3) . ?
N5 C4 1.391(3) . ?
N6 C4 1.399(3) . ?
C3 H3 0.95(2) . ?
C3 C4 1.439(3) . ?
O11 H11 0.90(3) . ?
O11 N7 1.420(2) . ?
N7 H7A 0.99(3) . ?
N7 H7B 0.97(3) . ?
N7 H7C 0.99(3) . ?
O12 N8 1.414(2) . ?
N8 H8A 0.94(3) . ?
N8 H8B 0.94(3) . ?
N8 H8C 0.91(3) . ?
N9 H9A 0.96(3) . ?
N9 H9B 0.87(4) . ?
N9 H9C 0.94(4) . ?
N9 H9D 0.96(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
N1 O1 H1 103.6(17) . . ?
C1 N1 O1 109.44(16) . . ?
O2 N2 O3 119.69(16) . . ?
O2 N2 C2 117.10(16) . . ?
O3 N2 C2 123.22(17) . . ?
O4 N3 C2 122.49(16) . . ?
O5 N3 O4 120.03(16) . . ?
O5 N3 C2 117.47(16) . . ?
N1 C1 H1A 121.0(15) . . ?
N1 C1 C2 126.19(19) . . ?
C2 C1 H1A 112.9(15) . . ?
N2 C2 N3 119.66(17) . . ?
N2 C2 C1 123.33(18) . . ?
N3 C2 C1 116.94(17) . . ?
N4 O6 H6 102.9(15) . . ?
C3 N4 O6 108.05(16) . . ?
O7 N5 O8 120.02(16) . . ?
O7 N5 C4 117.12(16) . . ?
O8 N5 C4 122.86(16) . . ?
O9 N6 O10 119.38(17) . . ?
O9 N6 C4 122.80(16) . . ?
O10 N6 C4 117.83(17) . . ?
N4 C3 H3 120.9(14) . . ?
N4 C3 C4 126.07(18) . . ?
C4 C3 H3 113.0(14) . . ?
N5 C4 N6 120.25(17) . . ?
N5 C4 C3 122.93(17) . . ?
N6 C4 C3 116.81(17) . . ?
N7 O11 H11 98.7(17) . . ?
O11 N7 H7A 112.4(15) . . ?
O11 N7 H7B 101.0(14) . . ?
O11 N7 H7C 106.3(14) . . ?
H7A N7 H7B 113(2) . . ?
H7A N7 H7C 110(2) . . ?
H7B N7 H7C 113(2) . . ?
O12 N8 H8A 108.8(14) . . ?
O12 N8 H8B 109.6(15) . . ?
O12 N8 H8C 105.8(15) . . ?
H8A N8 H8B 106(2) . . ?
H8A N8 H8C 115(2) . . ?
H8B N8 H8C 112(2) . . ?
H9A N9 H9B 111(3) . . ?
H9A N9 H9C 107(3) . . ?
H9A N9 H9D 113(2) . . ?
H9B N9 H9C 109(3) . . ?
H9B N9 H9D 109(3) . . ?
H9C N9 H9D 108(3) . . ?

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
_geom_hbond_publ_flag
O1 H1 O12 0.89(3) 1.73(3) 2.620(2) 176(3) 2_666 yes
O6 H6 O4 0.91(3) 1.90(3) 2.779(2) 162(2) 1_445 yes
O11 H11 O12 0.90(3) 1.66(3) 2.5595(19) 175(3) 2_666 yes
N7 H7A O2 0.99(3) 2.12(3) 2.825(2) 127(2) . yes
N7 H7B O8 0.97(3) 1.98(3) 2.834(2) 145(2) 2_676 yes
N7 H7C O12 0.99(3) 1.75(3) 2.703(2) 161(2) . yes
N8 H8B O4 0.94(3) 2.11(3) 2.829(2) 132(2) 1_445 yes
N8 H8C O7 0.91(3) 2.12(2) 2.761(2) 126.5(19) . yes
N9 H9A O8 0.96(3) 1.97(3) 2.838(2) 149(3) 1_545 yes

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id YP-031B
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shr37
_database_code_depnum_ccdc_archive 'CCDC 1847186'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2016-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 N4 O8, 2(H4 N)'
_chemical_formula_sum            'C2 H8 N6 O8'
_chemical_formula_weight         244.14
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.2546(11)
_cell_length_b                   7.8000(9)
_cell_length_c                   13.1353(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.923(3)
_cell_angle_gamma                90
_cell_volume                     902.17(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6471
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      3.08
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0526 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.9504.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20104
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.540
_diffrn_reflns_theta_min         3.079
_diffrn_ambient_temperature      130
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2168
_reflns_number_total             2763
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.067
_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)+(0.0389P)²+0.3038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          ?
# start Validation Reply Form
_vrf_PLAT110_shr37               
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: This is a pseudo condition. Examination of the data and 
application of the proposed translation resulted in a less reliable model 
that exhibits elongated ellipsoids dissimilar to adjacent atoms. 
This indicates that the proposed centering is a pseudo condition. 
;
_vrf_PLAT112_shr37               
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem.        A        100 %Fit  
RESPONSE: This is a pseudo condition. Application of the proposed higher 
symmetry resulted in a less reliable model that exhibits elongated 
ellipsoids dissimilar to adjacent atoms. This indicates that the proposed 
centering is a pseudo condition. 
;
_vrf_PLAT113_shr37               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       C2/c Check 
RESPONSE: Upon examination of the data in the program XPREP the centering 
condition does not appear. However, the structure is able to be solved in 
C2/c resulting in a less reliable model that exhibits elongated ellipsoids
dissimilar to adjacent atoms. These observations indicate that the proposed 
centering is a pseudo condition and the best representation of the 
structure is in the primitive setting.
;
# end Validation Reply Form
_olex2_refinement_description    
;
;
_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 0.69782(10) 0.02204(11) 0.35176(7) 0.0165(2) Uani 1 1 d . . . . .
O2 O 0.47137(10) 0.11138(13) 0.33961(7) 0.0200(2) Uani 1 1 d . . . . .
O3 O 0.44619(9) 0.22648(12) 0.51835(6) 0.0166(2) Uani 1 1 d . . . . .
O4 O 0.65521(10) 0.31886(11) 0.63429(6) 0.01394(18) Uani 1 1 d . . . . .
O5 O 0.84036(10) 0.01516(11) 0.65867(7) 0.0177(2) Uani 1 1 d . . . . .
O6 O 1.04735(10) 0.15836(12) 0.67709(7) 0.0181(2) Uani 1 1 d . . . . .
O7 O 1.06211(9) 0.27824(13) 0.49532(7) 0.0192(2) Uani 1 1 d . . . . .
O8 O 0.84411(10) 0.34937(11) 0.38142(6) 0.01444(19) Uani 1 1 d . . . . .
N1 N 0.60848(11) 0.10319(13) 0.38692(8) 0.0119(2) Uani 1 1 d . . . . .
N2 N 0.58808(10) 0.24695(12) 0.54423(7) 0.01017(19) Uani 1 1 d . . . . .
N3 N 0.91501(11) 0.12132(13) 0.62542(8) 0.0114(2) Uani 1 1 d . . . . .
N4 N 0.91961(10) 0.28037(13) 0.46913(7) 0.0106(2) Uani 1 1 d . . . . .
C1 C 0.67583(12) 0.19144(15) 0.48563(9) 0.0102(2) Uani 1 1 d . . . . .
C2 C 0.83872(12) 0.20373(15) 0.52763(9) 0.0107(2) Uani 1 1 d . . . . .
N6 N 0.67536(12) 0.65719(15) 0.31367(9) 0.0134(2) Uani 1 1 d . . . . .
H6A H 0.622(2) 0.688(2) 0.3576(14) 0.033(5) Uiso 1 1 d . . . . .
H6B H 0.6617(18) 0.727(2) 0.2587(13) 0.027(4) Uiso 1 1 d . . . . .
H6C H 0.775(2) 0.662(2) 0.3509(15) 0.037(5) Uiso 1 1 d . . . . .
H6D H 0.6547(19) 0.555(3) 0.2913(14) 0.032(5) Uiso 1 1 d . . . . .
N5 N 0.21342(13) 0.34733(14) 0.33733(9) 0.0135(2) Uani 1 1 d . . . . .
H5A H 0.2413(19) 0.459(2) 0.3398(13) 0.029(4) Uiso 1 1 d . . . . .
H5B H 0.1443(19) 0.334(2) 0.3737(13) 0.028(4) Uiso 1 1 d . . . . .
H5C H 0.1778(18) 0.311(2) 0.2716(14) 0.023(4) Uiso 1 1 d . . . . .
H5D H 0.295(2) 0.288(2) 0.3684(14) 0.034(5) 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 N1 1.2380(12) . ?
O2 N1 1.2309(13) . ?
O3 N2 1.2612(12) . ?
O4 N2 1.2837(12) . ?
O5 N3 1.2407(13) . ?
O6 N3 1.2380(12) . ?
O7 N4 1.2565(12) . ?
O8 N4 1.2687(12) . ?
N1 C1 1.4304(14) . ?
N2 C1 1.3506(14) . ?
N3 C2 1.4153(14) . ?
N4 C2 1.3646(14) . ?
C1 C2 1.4403(16) . ?
N6 H6A 0.897(18) . ?
N6 H6B 0.881(18) . ?
N6 H6C 0.90(2) . ?
N6 H6D 0.853(19) . ?
N5 H5A 0.903(18) . ?
N5 H5B 0.915(17) . ?
N5 H5C 0.871(17) . ?
N5 H5D 0.873(19) . ?

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 C1 115.43(9) . . ?
O2 N1 O1 122.77(10) . . ?
O2 N1 C1 121.78(10) . . ?
O3 N2 O4 118.17(9) . . ?
O3 N2 C1 124.37(10) . . ?
O4 N2 C1 117.39(9) . . ?
O5 N3 C2 116.51(10) . . ?
O6 N3 O5 121.79(10) . . ?
O6 N3 C2 121.64(10) . . ?
O7 N4 O8 119.51(9) . . ?
O7 N4 C2 123.47(9) . . ?
O8 N4 C2 116.93(9) . . ?
N1 C1 C2 119.47(10) . . ?
N2 C1 N1 120.01(10) . . ?
N2 C1 C2 120.16(10) . . ?
N3 C2 C1 119.23(10) . . ?
N4 C2 N3 120.21(10) . . ?
N4 C2 C1 120.29(10) . . ?
H6A N6 H6B 113.1(15) . . ?
H6A N6 H6C 108.2(15) . . ?
H6A N6 H6D 111.3(16) . . ?
H6B N6 H6C 106.3(15) . . ?
H6B N6 H6D 109.6(16) . . ?
H6C N6 H6D 108.1(16) . . ?
H5A N5 H5B 109.3(15) . . ?
H5A N5 H5C 111.5(15) . . ?
H5A N5 H5D 107.4(16) . . ?
H5B N5 H5C 111.5(14) . . ?
H5B N5 H5D 109.7(15) . . ?
H5C N5 H5D 107.3(15) . . ?

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
N6 H6A O3 0.897(18) 2.035(19) 2.9129(14) 165.8(15) 3_666
N6 H6B O8 0.881(18) 2.060(18) 2.9261(14) 167.4(15) 2_655
N6 H6C O6 0.90(2) 2.270(19) 2.9118(14) 127.6(15) 3_766
N6 H6C O7 0.90(2) 2.166(19) 2.9496(14) 144.6(16) 3_766
N6 H6D O6 0.853(19) 2.254(19) 3.0613(15) 157.8(16) 4_565
N5 H5A O4 0.903(18) 1.961(19) 2.8491(14) 167.3(15) 3_666
N5 H5B O7 0.915(17) 2.016(18) 2.8890(14) 159.0(15) 1_455
N5 H5C O4 0.871(17) 2.022(17) 2.8634(14) 161.9(15) 4_565
N5 H5D O2 0.873(19) 2.254(19) 3.0072(15) 144.4(15) .
N5 H5D O3 0.873(19) 2.091(18) 2.8337(14) 142.5(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
O1 N1 C1 N2 -163.40(10) . . . . ?
O1 N1 C1 C2 9.74(15) . . . . ?
O2 N1 C1 N2 18.15(16) . . . . ?
O2 N1 C1 C2 -168.70(10) . . . . ?
O3 N2 C1 N1 0.13(17) . . . . ?
O3 N2 C1 C2 -172.97(10) . . . . ?
O4 N2 C1 N1 177.10(9) . . . . ?
O4 N2 C1 C2 4.00(15) . . . . ?
O5 N3 C2 N4 -160.14(10) . . . . ?
O5 N3 C2 C1 13.88(15) . . . . ?
O6 N3 C2 N4 22.66(16) . . . . ?
O6 N3 C2 C1 -163.32(10) . . . . ?
O7 N4 C2 N3 2.35(17) . . . . ?
O7 N4 C2 C1 -171.61(10) . . . . ?
O8 N4 C2 N3 178.85(10) . . . . ?
O8 N4 C2 C1 4.90(16) . . . . ?
N1 C1 C2 N3 -114.93(12) . . . . ?
N1 C1 C2 N4 59.08(15) . . . . ?
N2 C1 C2 N3 58.21(15) . . . . ?
N2 C1 C2 N4 -127.78(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
