# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shr31
_database_code_depnum_ccdc_archive 'CCDC 1439832'
_audit_update_record             
;
2015-12-01 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;
_audit_creation_date             2015-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 N6 O3, C H6 N3'
_chemical_formula_sum            'C5 H9 N9 O3'
_chemical_formula_weight         243.21
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1162(6)
_cell_length_b                   7.8445(5)
_cell_length_c                   14.1930(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.811(2)
_cell_angle_gamma                90
_cell_volume                     981.25(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0463 before and 0.0438 after correction.
The Ratio of minimum to maximum transmission is 0.9564.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38245
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.613
_diffrn_reflns_theta_min         2.969
_diffrn_ambient_temperature      100
_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 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_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                2475
_reflns_number_total             3012
_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         0.559
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.3830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0882
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.33488(8) 1.00128(9) 0.58098(5) 0.01456(16) Uani 1 1 d . . . . .
O2 O -0.27163(9) 0.57187(10) 0.45965(6) 0.01858(17) Uani 1 1 d . . . . .
O3 O -0.22950(9) 0.47963(10) 0.32407(5) 0.01810(17) Uani 1 1 d . . . . .
N1 N -0.00977(10) 0.82568(11) 0.59152(6) 0.01307(17) Uani 1 1 d . . . . .
N2 N 0.11491(10) 0.92000(11) 0.62692(6) 0.01318(17) Uani 1 1 d . . . . .
N3 N 0.20720(9) 0.91265(10) 0.56576(6) 0.01146(17) Uani 1 1 d . . . . .
N4 N 0.15899(9) 0.74535(11) 0.40538(6) 0.01207(17) Uani 1 1 d . . . . .
N5 N 0.03778(9) 0.64752(11) 0.36445(6) 0.01305(17) Uani 1 1 d . . . . .
N6 N -0.19434(10) 0.56344(11) 0.39999(6) 0.01354(17) Uani 1 1 d . . . . .
C1 C -0.05451(11) 0.65547(12) 0.42355(7) 0.01221(19) Uani 1 1 d . . . . .
C2 C 0.00629(11) 0.75761(12) 0.50679(7) 0.01140(18) Uani 1 1 d . . . . .
C3 C 0.14205(11) 0.81035(12) 0.49068(7) 0.01105(18) Uani 1 1 d . . . . .
C4 C 0.29110(12) 0.75033(15) 0.36555(8) 0.0166(2) Uani 1 1 d . . . . .
H4A H 0.2597(16) 0.7184(19) 0.2993(11) 0.022(3) Uiso 1 1 d . . . . .
H4B H 0.3658(18) 0.671(2) 0.4026(11) 0.031(4) Uiso 1 1 d . . . . .
H4C H 0.3278(17) 0.865(2) 0.3702(11) 0.025(4) Uiso 1 1 d . . . . .
N7 N 0.44384(11) 0.34304(13) 0.27139(7) 0.01636(19) Uani 1 1 d . . . . .
H7A H 0.538(2) 0.355(2) 0.2960(12) 0.033(4) Uiso 1 1 d . . . . .
H7B H 0.4043(17) 0.3960(19) 0.2172(11) 0.024(4) Uiso 1 1 d . . . . .
N8 N 0.40813(10) 0.20211(12) 0.40630(6) 0.01495(18) Uani 1 1 d . . . . .
H8A H 0.3491(17) 0.1821(19) 0.4454(11) 0.023(4) Uiso 1 1 d . . . . .
H8B H 0.4966(18) 0.148(2) 0.4138(11) 0.028(4) Uiso 1 1 d . . . . .
N9 N 0.20667(10) 0.33402(11) 0.29977(7) 0.01389(17) Uani 1 1 d . . . . .
H9A H 0.1733(17) 0.405(2) 0.2522(11) 0.024(4) Uiso 1 1 d . . . . .
H9B H 0.1432(18) 0.285(2) 0.3292(11) 0.030(4) Uiso 1 1 d . . . . .
C5 C 0.35155(11) 0.29348(12) 0.32585(7) 0.01177(19) 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
O1 N3 1.3252(11) . ?
O2 N6 1.2340(11) . ?
O3 N6 1.2327(11) . ?
N1 N2 1.3416(12) . ?
N1 C2 1.3575(13) . ?
N2 N3 1.3558(12) . ?
N3 C3 1.3449(12) . ?
N4 N5 1.3488(12) . ?
N4 C3 1.3584(12) . ?
N4 C4 1.4559(13) . ?
N5 C1 1.3328(13) . ?
N6 C1 1.4283(13) . ?
C1 C2 1.4178(14) . ?
C2 C3 1.3784(13) . ?
C4 H4A 0.944(15) . ?
C4 H4B 0.970(16) . ?
C4 H4C 0.955(16) . ?
N7 H7A 0.843(17) . ?
N7 H7B 0.867(16) . ?
N7 C5 1.3376(13) . ?
N8 H8A 0.880(16) . ?
N8 H8B 0.893(16) . ?
N8 C5 1.3350(13) . ?
N9 H9A 0.866(16) . ?
N9 H9B 0.885(17) . ?
N9 C5 1.3162(13) . ?

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
N2 N1 C2 106.01(8) . . ?
N1 N2 N3 109.98(8) . . ?
O1 N3 N2 122.43(8) . . ?
O1 N3 C3 129.33(8) . . ?
C3 N3 N2 108.19(8) . . ?
N5 N4 C3 109.28(8) . . ?
N5 N4 C4 121.06(8) . . ?
C3 N4 C4 129.03(8) . . ?
C1 N5 N4 106.36(8) . . ?
O2 N6 C1 116.38(8) . . ?
O3 N6 O2 124.18(9) . . ?
O3 N6 C1 119.43(9) . . ?
N5 C1 N6 119.88(9) . . ?
N5 C1 C2 112.07(9) . . ?
C2 C1 N6 128.03(9) . . ?
N1 C2 C1 148.52(9) . . ?
N1 C2 C3 109.49(9) . . ?
C3 C2 C1 101.99(9) . . ?
N3 C3 N4 143.36(9) . . ?
N3 C3 C2 106.32(9) . . ?
N4 C3 C2 110.29(9) . . ?
N4 C4 H4A 108.0(9) . . ?
N4 C4 H4B 108.0(9) . . ?
N4 C4 H4C 108.0(9) . . ?
H4A C4 H4B 111.2(13) . . ?
H4A C4 H4C 109.2(13) . . ?
H4B C4 H4C 112.3(13) . . ?
H7A N7 H7B 117.6(15) . . ?
C5 N7 H7A 120.9(11) . . ?
C5 N7 H7B 118.1(10) . . ?
H8A N8 H8B 121.2(14) . . ?
C5 N8 H8A 118.0(10) . . ?
C5 N8 H8B 119.9(10) . . ?
H9A N9 H9B 120.4(14) . . ?
C5 N9 H9A 120.1(10) . . ?
C5 N9 H9B 119.4(10) . . ?
N8 C5 N7 119.19(9) . . ?
N9 C5 N7 120.09(9) . . ?
N9 C5 N8 120.72(9) . . ?

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
N7 H7A O3 0.843(17) 2.278(17) 3.0719(12) 157.0(15) 1_655
N7 H7B O1 0.867(16) 2.041(16) 2.8999(12) 170.9(14) 4_575
N8 H8A O1 0.880(16) 2.421(15) 3.1497(12) 140.4(12) 1_545
N8 H8B O1 0.893(16) 1.918(16) 2.8019(12) 170.0(15) 3_666
N9 H9A N2 0.866(16) 2.203(16) 3.0647(13) 173.1(14) 4_575
N9 H9B N1 0.885(17) 2.048(17) 2.9305(13) 175.0(14) 3_566

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 N3 C3 N4 1.2(2) . . . . ?
O1 N3 C3 C2 -176.26(9) . . . . ?
O2 N6 C1 N5 177.56(9) . . . . ?
O2 N6 C1 C2 -0.83(15) . . . . ?
O3 N6 C1 N5 -1.23(14) . . . . ?
O3 N6 C1 C2 -179.63(9) . . . . ?
N1 N2 N3 O1 176.60(8) . . . . ?
N1 N2 N3 C3 -0.85(11) . . . . ?
N1 C2 C3 N3 -0.75(11) . . . . ?
N1 C2 C3 N4 -179.11(8) . . . . ?
N2 N1 C2 C1 -178.49(15) . . . . ?
N2 N1 C2 C3 0.23(11) . . . . ?
N2 N3 C3 N4 178.39(13) . . . . ?
N2 N3 C3 C2 0.96(10) . . . . ?
N4 N5 C1 N6 -179.78(8) . . . . ?
N4 N5 C1 C2 -1.14(11) . . . . ?
N5 N4 C3 N3 -178.29(13) . . . . ?
N5 N4 C3 C2 -0.91(11) . . . . ?
N5 C1 C2 N1 179.35(15) . . . . ?
N5 C1 C2 C3 0.59(11) . . . . ?
N6 C1 C2 N1 -2.1(2) . . . . ?
N6 C1 C2 C3 179.09(9) . . . . ?
C1 C2 C3 N3 178.57(8) . . . . ?
C1 C2 C3 N4 0.20(10) . . . . ?
C2 N1 N2 N3 0.37(10) . . . . ?
C3 N4 N5 C1 1.24(10) . . . . ?
C4 N4 N5 C1 172.97(9) . . . . ?
C4 N4 C3 N3 10.8(2) . . . . ?
C4 N4 C3 C2 -171.78(10) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_shr33i2a
_database_code_depnum_ccdc_archive 'CCDC 1439833'
_audit_update_record             
;
2015-12-01 deposited with the CCDC.
2015-12-24 downloaded from the CCDC.
;
_audit_creation_date             2015-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 N6 O3, C H7 N4'
_chemical_formula_sum            'C5 H10 N10 O3'
_chemical_formula_weight         258.23
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   21.0998(14)
_cell_length_b                   3.8430(3)
_cell_length_c                   25.414(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.027(2)
_cell_angle_gamma                90
_cell_volume                     2057.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.31
_cell_measurement_theta_min      3.21
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0697 before and 0.0565 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    1.667
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            40862
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_min         3.211
_diffrn_ambient_temperature      100
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_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                2045
_reflns_number_total             2538
_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         0.317
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2538
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.111
_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)+(0.0370P)²+2.0812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0887
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.30582(4) 0.8313(3) 0.44813(4) 0.0163(2) Uani 1 1 d . . . . .
O3 O 0.40980(5) 0.0280(3) 0.22761(4) 0.0185(2) Uani 1 1 d . . . . .
O2 O 0.47765(5) -0.0060(3) 0.29510(4) 0.0193(2) Uani 1 1 d . . . . .
N6 N 0.42700(5) 0.0902(3) 0.27355(4) 0.0133(2) Uani 1 1 d . . . . .
N5 N 0.29903(5) 0.5334(3) 0.32668(4) 0.0124(2) Uani 1 1 d . . . . .
N1' N 0.35027(5) 1.1285(3) 0.54233(5) 0.0146(3) Uani 1 1 d . . . . .
N1 N 0.34695(5) 0.6654(3) 0.41951(4) 0.0124(2) Uani 1 1 d . . . . .
N4 N 0.32757(5) 0.3683(3) 0.28715(4) 0.0124(2) Uani 1 1 d . . . . .
N3 N 0.43746(5) 0.4128(3) 0.40205(4) 0.0151(3) Uani 1 1 d . . . . .
N2 N 0.40595(5) 0.5803(3) 0.43867(4) 0.0152(3) Uani 1 1 d . . . . .
N2' N 0.30230(6) 1.3105(4) 0.56765(5) 0.0176(3) Uani 1 1 d . . . . .
N4' N 0.44857(6) 0.8768(4) 0.54546(5) 0.0191(3) Uani 1 1 d . . . . .
N3' N 0.41219(6) 1.1401(4) 0.61972(5) 0.0201(3) Uani 1 1 d . . . . .
C3 C 0.38557(6) 0.2829(4) 0.30599(5) 0.0118(3) Uani 1 1 d . . . . .
C2 C 0.39686(6) 0.3926(4) 0.35876(5) 0.0119(3) Uani 1 1 d . . . . .
C1 C 0.34044(6) 0.5500(4) 0.36961(5) 0.0116(3) Uani 1 1 d . . . . .
C1' C 0.40392(6) 1.0480(4) 0.56941(5) 0.0139(3) Uani 1 1 d . . . . .
C4 C 0.23541(6) 0.6782(4) 0.31842(6) 0.0144(3) Uani 1 1 d . . . . .
H3'A H 0.4480(9) 1.093(5) 0.6364(7) 0.023(5) Uiso 1 1 d . . . . .
H4A H 0.2091(9) 0.507(5) 0.2991(7) 0.027(5) Uiso 1 1 d . . . . .
H4B H 0.2189(8) 0.723(5) 0.3512(7) 0.022(4) Uiso 1 1 d . . . . .
H2'A H 0.2667(9) 1.170(5) 0.5665(7) 0.031(5) Uiso 1 1 d . . . . .
H4'A H 0.4825(9) 0.805(5) 0.5627(7) 0.030(5) Uiso 1 1 d . . . . .
H4C H 0.2379(8) 0.897(5) 0.2990(7) 0.022(4) Uiso 1 1 d . . . . .
H4'B H 0.4390(8) 0.803(5) 0.5120(7) 0.028(5) Uiso 1 1 d . . . . .
H3'B H 0.3832(9) 1.268(5) 0.6329(7) 0.027(5) Uiso 1 1 d . . . . .
H2'B H 0.2928(9) 1.497(6) 0.5466(8) 0.033(5) Uiso 1 1 d . . . . .
H1' H 0.3435(9) 1.041(5) 0.5107(8) 0.026(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 1.3249(15) . ?
O3 N6 1.2277(15) . ?
O2 N6 1.2315(14) . ?
N6 C3 1.4381(18) . ?
N5 N4 1.3558(16) . ?
N5 C1 1.3627(16) . ?
N5 C4 1.4580(17) . ?
N1' N2' 1.4131(17) . ?
N1' C1' 1.3298(17) . ?
N1' H1' 0.876(19) . ?
N1 N2 1.3526(15) . ?
N1 C1 1.3437(17) . ?
N4 C3 1.3316(17) . ?
N3 N2 1.3369(17) . ?
N3 C2 1.3604(17) . ?
N2' H2'A 0.92(2) . ?
N2' H2'B 0.91(2) . ?
N4' C1' 1.3234(19) . ?
N4' H4'A 0.87(2) . ?
N4' H4'B 0.910(19) . ?
N3' C1' 1.3293(18) . ?
N3' H3'A 0.866(19) . ?
N3' H3'B 0.87(2) . ?
C3 C2 1.4141(18) . ?
C2 C1 1.3762(19) . ?
C4 H4A 0.975(19) . ?
C4 H4B 0.936(18) . ?
C4 H4C 0.977(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
O3 N6 O2 124.79(12) . . ?
O3 N6 C3 119.16(11) . . ?
O2 N6 C3 116.04(11) . . ?
N4 N5 C1 108.91(11) . . ?
N4 N5 C4 120.89(11) . . ?
C1 N5 C4 130.08(12) . . ?
N2' N1' H1' 121.4(12) . . ?
C1' N1' N2' 119.34(12) . . ?
C1' N1' H1' 118.6(12) . . ?
O1 N1 N2 122.40(10) . . ?
O1 N1 C1 129.76(11) . . ?
C1 N1 N2 107.83(11) . . ?
C3 N4 N5 106.54(10) . . ?
N2 N3 C2 105.98(11) . . ?
N3 N2 N1 110.36(10) . . ?
N1' N2' H2'A 107.2(12) . . ?
N1' N2' H2'B 105.3(12) . . ?
H2'A N2' H2'B 106.8(17) . . ?
C1' N4' H4'A 121.0(12) . . ?
C1' N4' H4'B 117.2(12) . . ?
H4'A N4' H4'B 120.8(17) . . ?
C1' N3' H3'A 118.9(12) . . ?
C1' N3' H3'B 117.6(12) . . ?
H3'A N3' H3'B 123.0(17) . . ?
N4 C3 N6 119.73(11) . . ?
N4 C3 C2 111.90(12) . . ?
C2 C3 N6 128.33(12) . . ?
N3 C2 C3 148.36(13) . . ?
N3 C2 C1 109.11(12) . . ?
C1 C2 C3 102.53(11) . . ?
N5 C1 C2 110.11(12) . . ?
N1 C1 N5 143.17(13) . . ?
N1 C1 C2 106.72(11) . . ?
N4' C1' N1' 119.00(13) . . ?
N4' C1' N3' 120.94(13) . . ?
N3' C1' N1' 120.06(13) . . ?
N5 C4 H4A 108.1(11) . . ?
N5 C4 H4B 108.9(11) . . ?
N5 C4 H4C 109.1(10) . . ?
H4A C4 H4B 110.0(15) . . ?
H4A C4 H4C 111.6(14) . . ?
H4B C4 H4C 109.0(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
N3' H3'A O2 0.866(19) 2.305(19) 3.1341(16) 160.3(16) 5_666
N2' H2'A O1 0.92(2) 2.03(2) 2.9429(17) 170.0(17) 2_556
N4' H4'A N3 0.87(2) 2.05(2) 2.9090(17) 173.5(18) 5_666
N4' H4'B N2 0.910(19) 2.134(19) 3.0359(17) 171.3(17) .
N2' H2'B O1 0.91(2) 2.46(2) 3.0455(16) 122.8(15) 2_566
N1' H1' O1 0.876(19) 1.917(19) 2.7709(15) 164.4(17) .

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 N2 N3 179.53(12) . . . . ?
O1 N1 C1 N5 0.7(3) . . . . ?
O1 N1 C1 C2 -179.44(13) . . . . ?
O3 N6 C3 N4 4.97(19) . . . . ?
O3 N6 C3 C2 -177.50(13) . . . . ?
O2 N6 C3 N4 -173.82(12) . . . . ?
O2 N6 C3 C2 3.7(2) . . . . ?
N6 C3 C2 N3 3.0(3) . . . . ?
N6 C3 C2 C1 -177.59(13) . . . . ?
N5 N4 C3 N6 177.54(12) . . . . ?
N5 N4 C3 C2 -0.37(15) . . . . ?
N4 N5 C1 N1 179.39(18) . . . . ?
N4 N5 C1 C2 -0.45(16) . . . . ?
N4 C3 C2 N3 -179.3(2) . . . . ?
N4 C3 C2 C1 0.10(15) . . . . ?
N3 C2 C1 N5 179.88(11) . . . . ?
N3 C2 C1 N1 -0.02(16) . . . . ?
N2 N1 C1 N5 -179.87(18) . . . . ?
N2 N1 C1 C2 -0.02(15) . . . . ?
N2 N3 C2 C3 179.4(2) . . . . ?
N2 N3 C2 C1 0.06(16) . . . . ?
N2' N1' C1' N4' 179.86(14) . . . . ?
N2' N1' C1' N3' -0.3(2) . . . . ?
C3 C2 C1 N5 0.21(15) . . . . ?
C3 C2 C1 N1 -179.69(11) . . . . ?
C2 N3 N2 N1 -0.07(15) . . . . ?
C1 N5 N4 C3 0.50(15) . . . . ?
C1 N1 N2 N3 0.06(15) . . . . ?
C4 N5 N4 C3 176.95(12) . . . . ?
C4 N5 C1 N1 3.4(3) . . . . ?
C4 N5 C1 C2 -176.48(14) . . . . ?

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