# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s2
_database_code_depnum_ccdc_archive 'CCDC 1553709'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1-ethyl-3-methylimdazolium acetate 4,5-di(amidoximyl)imidazole'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H22 N8 O4'
_chemical_formula_weight         354.38

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   15.164(10)
_cell_length_b                   15.217(10)
_cell_length_c                   15.529(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3583(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1879
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.17

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46302
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.1274
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         26.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3695
_reflns_number_gt                1879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1009P)²+6.9678P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3695
_refine_ls_number_parameters     250
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2362
_refine_ls_wR_factor_gt          0.1812
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3747(3) -0.1102(3) 0.2212(3) 0.0735(12) Uani 1 1 d . U . . .
C2 C 0.3574(3) -0.0600(3) 0.2877(3) 0.0553(11) Uani 1 1 d . U . . .
H2 H 0.3091 -0.0207 0.2930 0.066 Uiso 1 1 calc R U . . .
N3 N 0.4185(3) -0.0740(3) 0.3450(3) 0.0887(14) Uani 1 1 d . U . . .
C4 C 0.4759(4) -0.1349(5) 0.3126(6) 0.110(2) Uani 1 1 d . U . . .
H4A H 0.5268 -0.1568 0.3411 0.132 Uiso 1 1 calc R U . . .
C5 C 0.4496(5) -0.1572(5) 0.2381(6) 0.107(2) Uani 1 1 d . U . . .
H5 H 0.4769 -0.1988 0.2010 0.128 Uiso 1 1 calc R U . . .
C6 C 0.3250(6) -0.1093(5) 0.1365(5) 0.127(3) Uani 1 1 d . U . . .
H6A H 0.3351 -0.0527 0.1067 0.152 Uiso 1 1 calc R U . . .
H6B H 0.3470 -0.1571 0.0990 0.152 Uiso 1 1 calc R U . . .
C7 C 0.2341(6) -0.1207(5) 0.1513(5) 0.133(3) Uani 1 1 d . U . . .
H7A H 0.2241 -0.1771 0.1801 0.199 Uiso 1 1 calc R U . . .
H7B H 0.2026 -0.1199 0.0962 0.199 Uiso 1 1 calc R U . . .
H7C H 0.2123 -0.0729 0.1879 0.199 Uiso 1 1 calc R U . . .
C8 C 0.4169(6) -0.0307(5) 0.4304(5) 0.137(2) Uani 1 1 d . U . . .
H8A H 0.4592 0.0179 0.4310 0.206 Uiso 1 1 calc R U . . .
H8B H 0.4327 -0.0735 0.4749 0.206 Uiso 1 1 calc R U . . .
H8C H 0.3575 -0.0080 0.4417 0.206 Uiso 1 1 calc R U . . .
O1 O 0.04768(18) 0.0827(2) 0.28092(19) 0.0597(9) Uani 1 1 d . U . . .
O2 O 0.19041(17) 0.05301(19) 0.28783(17) 0.0491(7) Uani 1 1 d . U . . .
C9 C 0.1137(3) 0.0482(2) 0.3165(2) 0.0396(9) Uani 1 1 d . U . . .
C10 C 0.0972(4) -0.0006(4) 0.3996(3) 0.0749(16) Uani 1 1 d . U . . .
H10A H 0.1497 0.0031 0.4362 0.112 Uiso 1 1 calc R U . . .
H10B H 0.0842 -0.0623 0.3869 0.112 Uiso 1 1 calc R U . . .
H10C H 0.0469 0.0259 0.4296 0.112 Uiso 1 1 calc R U . . .
N11 N -0.2188(2) 0.2122(2) 0.1248(2) 0.0424(8) Uani 1 1 d . U . . .
H11 H -0.206(3) 0.188(3) 0.168(3) 0.051 Uiso 1 1 d . U . . .
C12 C -0.3020(3) 0.2361(3) 0.1058(3) 0.0449(10) Uani 1 1 d . U . . .
H12 H -0.3518 0.2210 0.1399 0.054 Uiso 1 1 calc R U . . .
N13 N -0.30659(19) 0.2829(2) 0.0346(2) 0.0419(8) Uani 1 1 d . U . . .
C14 C -0.2194(2) 0.2896(2) 0.0064(2) 0.0352(8) Uani 1 1 d . U . . .
C15 C -0.1638(2) 0.2451(2) 0.0619(2) 0.0335(8) Uani 1 1 d . U . . .
C16 C -0.0698(2) 0.2232(2) 0.0671(2) 0.0374(9) Uani 1 1 d . U . . .
N17 N -0.0503(2) 0.1715(3) 0.1301(2) 0.0530(10) Uani 1 1 d . U . . .
O3 O 0.04176(18) 0.1523(2) 0.1291(2) 0.0651(10) Uani 1 1 d . U . . .
H3 H 0.045(4) 0.131(4) 0.185(4) 0.098 Uiso 1 1 d . U . . .
N18 N -0.0121(2) 0.2553(3) 0.0088(3) 0.0546(10) Uani 1 1 d . U . . .
H18A H -0.028(3) 0.286(3) -0.031(3) 0.065 Uiso 1 1 d . U . . .
H18B H 0.039(3) 0.241(3) 0.013(3) 0.065 Uiso 1 1 d . U . . .
C19 C -0.2031(2) 0.3371(3) -0.0748(3) 0.0415(9) Uani 1 1 d . U . . .
N20 N -0.1229(2) 0.3483(2) -0.1005(2) 0.0467(9) Uani 1 1 d . U . . .
O4 O -0.12316(19) 0.3926(2) -0.1814(2) 0.0665(10) Uani 1 1 d . U . . .
H4 H -0.065(4) 0.399(4) -0.195(4) 0.100 Uiso 1 1 d . U . . .
N21 N -0.2744(2) 0.3663(4) -0.1171(3) 0.0829(17) Uani 1 1 d . U . . .
H21A H -0.322(4) 0.352(4) -0.097(4) 0.100 Uiso 1 1 d . U . . .
H21B H -0.270(4) 0.386(4) -0.166(4) 0.100 Uiso 1 1 d . U . . .


_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 C2 1.311(6) . ?
N1 C5 1.368(7) . ?
N1 C6 1.516(8) . ?
C2 N3 1.302(6) . ?
C2 H2 0.9500 . ?
N3 C4 1.367(9) . ?
N3 C8 1.481(9) . ?
C4 C5 1.271(10) . ?
C4 H4A 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.407(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O1 C9 1.258(4) . ?
O2 C9 1.248(4) . ?
C9 C10 1.509(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N11 C12 1.346(5) . ?
N11 C15 1.378(5) . ?
N11 H11 0.79(4) . ?
C12 N13 1.317(5) . ?
C12 H12 0.9500 . ?
N13 C14 1.397(4) . ?
C14 C15 1.383(5) . ?
C14 C19 1.475(5) . ?
C15 C16 1.465(5) . ?
C16 N17 1.290(5) . ?
C16 N18 1.351(5) . ?
N17 O3 1.427(4) . ?
O3 H3 0.92(6) . ?
N18 H18A 0.81(5) . ?
N18 H18B 0.81(5) . ?
C19 N20 1.291(5) . ?
C19 N21 1.342(5) . ?
N20 O4 1.426(4) . ?
O4 H4 0.91(6) . ?
N21 H21A 0.81(6) . ?
N21 H21B 0.83(6) . ?

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
C2 N1 C5 108.7(6) . . ?
C2 N1 C6 125.3(5) . . ?
C5 N1 C6 125.8(6) . . ?
N1 C2 N3 107.5(5) . . ?
N1 C2 H2 126.3 . . ?
N3 C2 H2 126.3 . . ?
C2 N3 C4 108.2(6) . . ?
C2 N3 C8 121.8(6) . . ?
C4 N3 C8 129.9(6) . . ?
C5 C4 N3 108.5(6) . . ?
C5 C4 H4A 125.8 . . ?
N3 C4 H4A 125.8 . . ?
C4 C5 N1 107.2(7) . . ?
C4 C5 H5 126.4 . . ?
N1 C5 H5 126.4 . . ?
C7 C6 N1 110.2(7) . . ?
C7 C6 H6A 109.6 . . ?
N1 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
N1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 O1 124.0(4) . . ?
O2 C9 C10 119.3(4) . . ?
O1 C9 C10 116.7(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 N11 C15 108.4(3) . . ?
C12 N11 H11 123(3) . . ?
C15 N11 H11 129(3) . . ?
N13 C12 N11 112.2(3) . . ?
N13 C12 H12 123.9 . . ?
N11 C12 H12 123.9 . . ?
C12 N13 C14 104.7(3) . . ?
C15 C14 N13 110.3(3) . . ?
C15 C14 C19 132.1(3) . . ?
N13 C14 C19 117.6(3) . . ?
N11 C15 C14 104.4(3) . . ?
N11 C15 C16 117.9(3) . . ?
C14 C15 C16 137.6(3) . . ?
N17 C16 N18 125.5(4) . . ?
N17 C16 C15 113.8(3) . . ?
N18 C16 C15 120.7(3) . . ?
C16 N17 O3 109.9(3) . . ?
N17 O3 H3 97(3) . . ?
C16 N18 H18A 122(3) . . ?
C16 N18 H18B 118(3) . . ?
H18A N18 H18B 120(5) . . ?
N20 C19 N21 124.3(4) . . ?
N20 C19 C14 119.2(3) . . ?
N21 C19 C14 116.5(3) . . ?
C19 N20 O4 109.4(3) . . ?
N20 O4 H4 105(4) . . ?
C19 N21 H21A 116(4) . . ?
C19 N21 H21B 121(4) . . ?
H21A N21 H21B 121(6) . . ?

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
C5 N1 C2 N3 0.0(6) . . . . ?
C6 N1 C2 N3 -174.5(6) . . . . ?
N1 C2 N3 C4 0.2(6) . . . . ?
N1 C2 N3 C8 -177.1(5) . . . . ?
C2 N3 C4 C5 -0.4(7) . . . . ?
C8 N3 C4 C5 176.6(6) . . . . ?
N3 C4 C5 N1 0.4(8) . . . . ?
C2 N1 C5 C4 -0.3(7) . . . . ?
C6 N1 C5 C4 174.2(7) . . . . ?
C2 N1 C6 C7 -53.8(9) . . . . ?
C5 N1 C6 C7 132.6(7) . . . . ?
C15 N11 C12 N13 -0.1(5) . . . . ?
N11 C12 N13 C14 -0.3(4) . . . . ?
C12 N13 C14 C15 0.6(4) . . . . ?
C12 N13 C14 C19 178.4(3) . . . . ?
C12 N11 C15 C14 0.5(4) . . . . ?
C12 N11 C15 C16 -176.9(3) . . . . ?
N13 C14 C15 N11 -0.7(4) . . . . ?
C19 C14 C15 N11 -178.0(4) . . . . ?
N13 C14 C15 C16 175.9(4) . . . . ?
C19 C14 C15 C16 -1.4(8) . . . . ?
N11 C15 C16 N17 2.5(5) . . . . ?
C14 C15 C16 N17 -173.8(4) . . . . ?
N11 C15 C16 N18 -178.2(4) . . . . ?
C14 C15 C16 N18 5.6(7) . . . . ?
N18 C16 N17 O3 -0.5(6) . . . . ?
C15 C16 N17 O3 178.8(3) . . . . ?
C15 C14 C19 N20 -6.3(7) . . . . ?
N13 C14 C19 N20 176.5(4) . . . . ?
C15 C14 C19 N21 173.9(5) . . . . ?
N13 C14 C19 N21 -3.3(6) . . . . ?
N21 C19 N20 O4 -2.4(6) . . . . ?
C14 C19 N20 O4 177.8(3) . . . . ?

_refine_diff_density_max         0.548
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_ti7
_database_code_depnum_ccdc_archive 'CCDC 1553708'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1-ethyl-3-methylimdazolium acetate 3,5-diaminotriazole'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H19 N7 O2'
_chemical_formula_weight         269.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.0454(6)
_cell_length_b                   14.2329(18)
_cell_length_c                   18.305(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.205(4)
_cell_angle_gamma                90
_cell_volume                     1314.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.646
_cell_measurement_theta_max      26.487

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   0.7197
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23263
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.646
_diffrn_reflns_theta_max         26.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2699
_reflns_number_gt                2375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.5688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     interative
_atom_sites_solution_secondary   dimap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2699
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N5 N -0.43696(19) 0.85879(7) 0.33899(5) 0.0131(2) Uani 1 1 d . . . . .
H5 H -0.607(3) 0.8659(11) 0.3272(8) 0.026(4) Uiso 1 1 d . . . . .
N6 N -0.36169(19) 0.83244(7) 0.41044(5) 0.0142(2) Uani 1 1 d . . . . .
C11 C -0.1020(2) 0.84656(8) 0.41002(6) 0.0124(2) Uani 1 1 d . . . . .
N4 N -0.00465(18) 0.87997(7) 0.34529(5) 0.0123(2) Uani 1 1 d . . . . .
C12 C -0.2235(2) 0.88743(8) 0.30276(6) 0.0114(2) Uani 1 1 d . . . . .
N7 N 0.06235(19) 0.83235(7) 0.46930(5) 0.0166(2) Uani 1 1 d . . . . .
H7A H 0.2423 0.8277 0.4592 0.020 Uiso 1 1 d R U . . .
H7B H -0.0022 0.7965 0.5050 0.020 Uiso 1 1 d R U . . .
N8 N -0.23005(19) 0.92061(7) 0.23336(5) 0.0136(2) Uani 1 1 d . . . . .
H8A H -0.3823 0.9055 0.2067 0.016 Uiso 1 1 d R U . . .
H8B H -0.0770 0.9130 0.2053 0.016 Uiso 1 1 d R U . . .
N3 N 1.0344(2) 0.59920(7) 0.16697(6) 0.0165(2) Uani 1 1 d . . . . .
C2 C 1.1887(2) 0.57571(8) 0.22387(6) 0.0150(2) Uani 1 1 d . . . . .
H2 H 1.3381 0.5352 0.2224 0.018 Uiso 1 1 calc R U . . .
N1 N 1.09947(19) 0.61833(7) 0.28333(6) 0.0149(2) Uani 1 1 d . . . . .
C5 C 0.8784(2) 0.67018(8) 0.26326(7) 0.0182(3) Uani 1 1 d . . . . .
H5A H 0.7736 0.7071 0.2948 0.022 Uiso 1 1 calc R U . . .
C4 C 0.8383(2) 0.65896(9) 0.19083(7) 0.0196(3) Uani 1 1 d . . . . .
H4 H 0.7014 0.6868 0.1617 0.024 Uiso 1 1 calc R U . . .
C8 C 1.0693(3) 0.56827(10) 0.09134(7) 0.0231(3) Uani 1 1 d . . . . .
H8C H 1.2204 0.5251 0.0893 0.035 Uiso 1 1 calc R U . . .
H8D H 1.1025 0.6230 0.0603 0.035 Uiso 1 1 calc R U . . .
H8F H 0.9085 0.5360 0.0739 0.035 Uiso 1 1 calc R U . . .
C6 C 1.2172(2) 0.61166(9) 0.35752(7) 0.0189(3) Uani 1 1 d . . . . .
H6C H 1.2990 0.6726 0.3710 0.023 Uiso 1 1 calc R U . . .
H6D H 1.3586 0.5634 0.3581 0.023 Uiso 1 1 calc R U . . .
C7 C 1.0102(3) 0.58605(10) 0.41318(7) 0.0229(3) Uani 1 1 d . . . . .
H7C H 0.8732 0.6349 0.4139 0.034 Uiso 1 1 calc R U . . .
H7D H 1.0946 0.5811 0.4617 0.034 Uiso 1 1 calc R U . . .
H7F H 0.9290 0.5257 0.3999 0.034 Uiso 1 1 calc R U . . .
C10 C 0.0283(2) 0.85322(9) 0.05649(7) 0.0186(3) Uani 1 1 d . . . . .
H10A H 0.0481 0.8125 0.0138 0.028 Uiso 1 1 calc R U . . .
H10B H 0.0341 0.9191 0.0412 0.028 Uiso 1 1 calc R U . . .
H10C H -0.1420 0.8403 0.0792 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2527(2) 0.83411(8) 0.11127(6) 0.0131(2) Uani 1 1 d . . . . .
O1 O 0.26475(16) 0.88693(6) 0.16709(5) 0.0177(2) Uani 1 1 d . . . . .
O2 O 0.40982(17) 0.76832(6) 0.09872(5) 0.0207(2) 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
N5 C12 1.3402(15) . ?
N5 N6 1.4052(14) . ?
N5 H5 0.886(16) . ?
N6 C11 1.3256(15) . ?
C11 N7 1.3669(15) . ?
C11 N4 1.3770(15) . ?
N4 C12 1.3418(15) . ?
C12 N8 1.3551(15) . ?
N7 H7A 0.9325 . ?
N7 H7B 0.8958 . ?
N8 H8A 0.9263 . ?
N8 H8B 0.9427 . ?
N3 C2 1.3298(16) . ?
N3 C4 1.3827(17) . ?
N3 C8 1.4669(16) . ?
C2 N1 1.3328(16) . ?
C2 H2 0.9500 . ?
N1 C5 1.3808(16) . ?
N1 C6 1.4738(16) . ?
C5 C4 1.3466(19) . ?
C5 H5A 0.9500 . ?
C4 H4 0.9500 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8F 0.9800 . ?
C6 C7 1.5191(18) . ?
C6 H6C 0.9900 . ?
C6 H6D 0.9900 . ?
C7 H7C 0.9800 . ?
C7 H7D 0.9800 . ?
C7 H7F 0.9800 . ?
C10 C9 1.5211(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 O2 1.2513(15) . ?
C9 O1 1.2689(14) . ?

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
C12 N5 N6 109.72(9) . . ?
C12 N5 H5 128.9(10) . . ?
N6 N5 H5 119.9(10) . . ?
C11 N6 N5 101.66(9) . . ?
N6 C11 N7 123.80(11) . . ?
N6 C11 N4 115.33(10) . . ?
N7 C11 N4 120.84(10) . . ?
C12 N4 C11 102.85(9) . . ?
N5 C12 N4 110.42(10) . . ?
N5 C12 N8 124.46(10) . . ?
N4 C12 N8 125.11(10) . . ?
C11 N7 H7A 115.5 . . ?
C11 N7 H7B 116.1 . . ?
H7A N7 H7B 118.3 . . ?
C12 N8 H8A 114.6 . . ?
C12 N8 H8B 117.9 . . ?
H8A N8 H8B 111.5 . . ?
C2 N3 C4 108.56(10) . . ?
C2 N3 C8 125.72(11) . . ?
C4 N3 C8 125.71(11) . . ?
N3 C2 N1 108.84(10) . . ?
N3 C2 H2 125.6 . . ?
N1 C2 H2 125.6 . . ?
C2 N1 C5 108.11(10) . . ?
C2 N1 C6 125.92(10) . . ?
C5 N1 C6 125.97(10) . . ?
C4 C5 N1 107.60(11) . . ?
C4 C5 H5A 126.2 . . ?
N1 C5 H5A 126.2 . . ?
C5 C4 N3 106.87(11) . . ?
C5 C4 H4 126.6 . . ?
N3 C4 H4 126.6 . . ?
N3 C8 H8C 109.5 . . ?
N3 C8 H8D 109.5 . . ?
H8C C8 H8D 109.5 . . ?
N3 C8 H8F 109.5 . . ?
H8C C8 H8F 109.5 . . ?
H8D C8 H8F 109.5 . . ?
N1 C6 C7 111.33(10) . . ?
N1 C6 H6C 109.4 . . ?
C7 C6 H6C 109.4 . . ?
N1 C6 H6D 109.4 . . ?
C7 C6 H6D 109.4 . . ?
H6C C6 H6D 108.0 . . ?
C6 C7 H7C 109.5 . . ?
C6 C7 H7D 109.5 . . ?
H7C C7 H7D 109.5 . . ?
C6 C7 H7F 109.5 . . ?
H7C C7 H7F 109.5 . . ?
H7D C7 H7F 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C9 O1 124.85(11) . . ?
O2 C9 C10 118.58(10) . . ?
O1 C9 C10 116.57(10) . . ?

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
N5 H5 N4 0.886(16) 2.051(16) 2.8847(14) 156.6(14) 1_455
N7 H7A N6 0.93 2.21 3.1205(14) 166.3 1_655
N7 H7B O2 0.90 2.01 2.8869(13) 167.6 4_576
N8 H8A O1 0.93 1.93 2.8405(13) 168.4 1_455
N8 H8B O1 0.94 1.91 2.8392(13) 167.8 .
C2 H2 N4 0.95 2.68 3.4626(16) 140.5 2_645
C2 H2 N8 0.95 2.68 3.5855(16) 160.6 2_645
C5 H5A N5 0.95 2.55 3.4281(16) 154.6 1_655
C4 H4 O2 0.95 2.18 3.1282(15) 172.5 .
C6 H6D O1 0.99 2.63 3.2316(16) 119.6 2_645
C10 H10C O2 0.98 2.51 3.4490(16) 159.3 1_455

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_ti25
_database_code_depnum_ccdc_archive 'CCDC 1553710'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1-ethyl-3-methylimdazolium 4,5-dicyanoimidazolate 4,5-dicyanoimidazole'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N10'
_chemical_formula_weight         346.37

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   13.409(2)
_cell_length_b                   7.1954(12)
_cell_length_c                   36.229(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3495.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6096
_cell_measurement_theta_min      2.714
_cell_measurement_theta_max      26.457

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   0.5190
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29169
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.714
_diffrn_reflns_theta_max         26.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3577
_reflns_number_gt                2733
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+1.3034P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     interative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3577
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36110(11) 0.9044(2) 0.67995(4) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.39337(13) 0.9735(3) 0.64803(5) 0.0191(4) Uani 1 1 d . . . . .
H2 H 0.4610 0.9803 0.6403 0.023 Uiso 1 1 calc R U . . .
N3 N 0.31505(11) 1.0313(2) 0.62872(4) 0.0190(3) Uani 1 1 d . . . . .
C4 C 0.22979(13) 0.9974(2) 0.64874(5) 0.0188(4) Uani 1 1 d . . . . .
H4 H 0.1634 1.0244 0.6414 0.023 Uiso 1 1 calc R U . . .
C5 C 0.25834(13) 0.9183(3) 0.68090(5) 0.0196(4) Uani 1 1 d . . . . .
H5 H 0.2159 0.8796 0.7004 0.024 Uiso 1 1 calc R U . . .
C6 C 0.42637(14) 0.8225(3) 0.70845(5) 0.0216(4) Uani 1 1 d . . . . .
H6A H 0.4791 0.7478 0.6964 0.026 Uiso 1 1 calc R U . . .
H6B H 0.3867 0.7383 0.7243 0.026 Uiso 1 1 calc R U . . .
C7 C 0.47424(16) 0.9711(3) 0.73215(5) 0.0285(5) Uani 1 1 d . . . . .
H7A H 0.5146 1.0532 0.7166 0.043 Uiso 1 1 calc R U . . .
H7B H 0.5169 0.9124 0.7508 0.043 Uiso 1 1 calc R U . . .
H7C H 0.4222 1.0438 0.7445 0.043 Uiso 1 1 calc R U . . .
C8 C 0.31952(15) 1.1139(3) 0.59168(5) 0.0271(5) Uani 1 1 d . . . . .
H8A H 0.3737 1.2052 0.5907 0.041 Uiso 1 1 calc R U . . .
H8B H 0.2560 1.1754 0.5862 0.041 Uiso 1 1 calc R U . . .
H8C H 0.3318 1.0161 0.5734 0.041 Uiso 1 1 calc R U . . .
N9 N 0.73336(11) 0.4578(2) 0.61025(4) 0.0169(3) Uani 1 1 d . . . . .
C10 C 0.83311(13) 0.4518(2) 0.61497(5) 0.0192(4) Uani 1 1 d . . . . .
H10 H 0.8785 0.4856 0.5960 0.023 Uiso 1 1 calc R U . . .
N11 N 0.86363(11) 0.3952(2) 0.64810(4) 0.0182(3) Uani 1 1 d . . . . .
C12 C 0.77621(12) 0.3621(2) 0.66641(5) 0.0154(4) Uani 1 1 d . . . . .
C13 C 0.69598(13) 0.4000(2) 0.64342(5) 0.0156(4) Uani 1 1 d . . . . .
C14 C 0.59211(13) 0.3875(3) 0.65135(5) 0.0208(4) Uani 1 1 d . . . . .
N15 N 0.50891(12) 0.3777(3) 0.65858(5) 0.0325(4) Uani 1 1 d . . . . .
C16 C 0.77309(13) 0.2965(2) 0.70357(5) 0.0192(4) Uani 1 1 d . . . . .
N17 N 0.77037(12) 0.2437(2) 0.73353(4) 0.0280(4) Uani 1 1 d . . . . .
N18 N 0.66505(11) 0.5672(2) 0.54516(4) 0.0188(3) Uani 1 1 d . . . . .
H18 H 0.6897(19) 0.521(4) 0.5720(8) 0.023 Uiso 0.74(4) 1 d . U . . .
C19 C 0.71624(14) 0.5611(3) 0.51315(5) 0.0221(4) Uani 1 1 d . . . . .
H19 H 0.7810 0.5082 0.5112 0.027 Uiso 1 1 calc R U . . .
N20 N 0.66881(12) 0.6348(2) 0.48457(4) 0.0216(4) Uani 1 1 d . . . . .
C21 C 0.58055(13) 0.6925(2) 0.49943(5) 0.0170(4) Uani 1 1 d . . . . .
C22 C 0.57714(13) 0.6513(2) 0.53667(5) 0.0171(4) Uani 1 1 d . . . . .
C23 C 0.49934(13) 0.6785(2) 0.56298(5) 0.0198(4) Uani 1 1 d . . . . .
N24 N 0.43610(12) 0.6978(2) 0.58395(5) 0.0291(4) Uani 1 1 d . . . . .
N25 N 0.44801(13) 0.8605(2) 0.46005(5) 0.0292(4) Uani 1 1 d . . . . .
C26 C 0.50610(14) 0.7851(3) 0.47779(5) 0.0205(4) 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 C2 1.331(2) . ?
N1 C5 1.382(2) . ?
N1 C6 1.476(2) . ?
C2 N3 1.329(2) . ?
C2 H2 0.9500 . ?
N3 C4 1.376(2) . ?
N3 C8 1.469(2) . ?
C4 C5 1.352(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.514(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N9 C10 1.349(2) . ?
N9 C13 1.367(2) . ?
C10 N11 1.332(2) . ?
C10 H10 0.9500 . ?
N11 C12 1.368(2) . ?
C12 C13 1.388(2) . ?
C12 C16 1.427(3) . ?
C13 C14 1.425(2) . ?
C14 N15 1.148(2) . ?
C16 N17 1.151(2) . ?
N18 C19 1.348(2) . ?
N18 C22 1.360(2) . ?
N18 H18 1.08(3) . ?
C19 N20 1.326(2) . ?
C19 H19 0.9500 . ?
N20 C21 1.365(2) . ?
C21 C22 1.382(2) . ?
C21 C26 1.434(3) . ?
C22 C23 1.426(3) . ?
C23 N24 1.147(2) . ?
N25 C26 1.147(2) . ?

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
C2 N1 C5 108.60(15) . . ?
C2 N1 C6 124.33(15) . . ?
C5 N1 C6 127.04(15) . . ?
N3 C2 N1 108.50(15) . . ?
N3 C2 H2 125.7 . . ?
N1 C2 H2 125.7 . . ?
C2 N3 C4 108.89(15) . . ?
C2 N3 C8 125.13(15) . . ?
C4 N3 C8 125.97(15) . . ?
C5 C4 N3 107.08(15) . . ?
C5 C4 H4 126.5 . . ?
N3 C4 H4 126.5 . . ?
C4 C5 N1 106.93(15) . . ?
C4 C5 H5 126.5 . . ?
N1 C5 H5 126.5 . . ?
N1 C6 C7 111.47(15) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 N9 C13 104.02(14) . . ?
N11 C10 N9 115.39(16) . . ?
N11 C10 H10 122.3 . . ?
N9 C10 H10 122.3 . . ?
C10 N11 C12 103.11(14) . . ?
N11 C12 C13 109.83(15) . . ?
N11 C12 C16 122.69(15) . . ?
C13 C12 C16 127.47(16) . . ?
N9 C13 C12 107.64(15) . . ?
N9 C13 C14 123.71(16) . . ?
C12 C13 C14 128.63(17) . . ?
N15 C14 C13 178.5(2) . . ?
N17 C16 C12 179.9(2) . . ?
C19 N18 C22 105.16(15) . . ?
C19 N18 H18 127.5(14) . . ?
C22 N18 H18 127.3(14) . . ?
N20 C19 N18 114.47(16) . . ?
N20 C19 H19 122.8 . . ?
N18 C19 H19 122.8 . . ?
C19 N20 C21 103.27(15) . . ?
N20 C21 C22 110.41(15) . . ?
N20 C21 C26 121.96(16) . . ?
C22 C21 C26 127.62(17) . . ?
N18 C22 C21 106.69(15) . . ?
N18 C22 C23 122.93(16) . . ?
C21 C22 C23 130.33(16) . . ?
N24 C23 C22 178.9(2) . . ?
N25 C26 C21 178.6(2) . . ?

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
C2 H2 N11 0.95 2.45 3.307(2) 150.6 8_765
C4 H4 N15 0.95 2.62 3.334(2) 132.7 8_665
C5 H5 N17 0.95 2.59 3.367(3) 139.1 3_656
C6 H6B N17 0.99 2.60 3.421(3) 140.1 3_656
C7 H7C N17 0.98 2.62 3.587(3) 170.5 6_567
C8 H8B N24 0.98 2.58 3.492(3) 154.3 8_665
C10 H10 N25 0.95 2.49 3.403(2) 160.6 4_566
N18 H18 N9 1.08(3) 1.57(3) 2.649(2) 176(2) .
C19 H19 N25 0.95 2.64 3.304(3) 127.0 4_566

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_ti9
_database_code_depnum_ccdc_archive 'CCDC 1553711'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1-ethyl-3-methylimdazolium 2-methyl-4(5)-nitroimidazolate.2(2-methyl-4(5)-nitroimidazole)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H25 N11 O6'
_chemical_formula_weight         491.49

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.8397(5)
_cell_length_b                   8.9624(6)
_cell_length_c                   9.2212(7)
_cell_angle_alpha                116.269(2)
_cell_angle_beta                 98.816(3)
_cell_angle_gamma                93.667(2)
_cell_volume                     567.74(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6918
_cell_measurement_theta_min      2.515
_cell_measurement_theta_max      35.238

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             258
_exptl_transmission_factor_min   0.6949
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20561
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.515
_diffrn_reflns_theta_max         35.238
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.693
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.693
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.603
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6133
_reflns_number_gt                5627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     0.514
_reflns_Friedel_fraction_full    0.981

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.0811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     interative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6133
_refine_ls_number_parameters     327
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1246(2) 1.54086(18) 1.31389(18) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.0831(2) 1.4119(2) 1.3434(2) 0.0164(3) Uani 1 1 d . . . . .
H2 H 0.0390 1.4182 1.4360 0.020 Uiso 1 1 calc R U . . .
N3 N 0.1141(2) 1.27266(19) 1.22025(19) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.1756(3) 1.3142(3) 1.1085(3) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.2075 1.2387 1.0091 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1820(3) 1.4825(3) 1.1667(2) 0.0213(4) Uani 1 1 d . . . . .
H5 H 0.2188 1.5478 1.1161 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1177(3) 1.7177(2) 1.4271(2) 0.0213(4) Uani 1 1 d . . . . .
H6A H 0.2368 1.7823 1.4648 0.026 Uiso 1 1 calc R U . . .
H6B H 0.0763 1.7235 1.5254 0.026 Uiso 1 1 calc R U . . .
C7 C -0.0020(3) 1.7973(3) 1.3462(3) 0.0274(4) Uani 1 1 d . . . . .
H7A H 0.0405 1.7947 1.2507 0.041 Uiso 1 1 calc R U . . .
H7B H -0.0037 1.9142 1.4258 0.041 Uiso 1 1 calc R U . . .
H7C H -0.1203 1.7344 1.3098 0.041 Uiso 1 1 calc R U . . .
C8 C 0.0980(3) 1.1051(2) 1.2119(3) 0.0270(4) Uani 1 1 d . . . . .
H8A H 0.2123 1.0853 1.2540 0.041 Uiso 1 1 calc R U . . .
H8B H 0.0556 1.0198 1.0970 0.041 Uiso 1 1 calc R U . . .
H8C H 0.0153 1.0982 1.2791 0.041 Uiso 1 1 calc R U . . .
N1A N 0.3356(2) 0.4674(2) 0.8543(2) 0.0188(3) Uani 1 1 d . . . . .
C2A C 0.4006(2) 0.3475(2) 0.7415(2) 0.0184(4) Uani 1 1 d . . . . .
N3A N 0.4373(2) 0.3891(2) 0.6217(2) 0.0181(3) Uani 1 1 d . . . . .
H3A H 0.481(3) 0.330(3) 0.536(3) 0.022 Uiso 1 1 d . U . . .
C4A C 0.3940(2) 0.5448(2) 0.6610(2) 0.0172(3) Uani 1 1 d . . . . .
H4A H 0.4044 0.6089 0.6030 0.021 Uiso 1 1 calc R U . . .
C5A C 0.3319(2) 0.5883(2) 0.8029(2) 0.0173(4) Uani 1 1 d . . . . .
C6A C 0.4293(3) 0.1839(3) 0.7384(3) 0.0272(4) Uani 1 1 d . . . . .
H6AA H 0.4604 0.1996 0.8518 0.041 Uiso 1 1 calc R U . . .
H6AB H 0.5243 0.1416 0.6807 0.041 Uiso 1 1 calc R U . . .
H6AC H 0.3222 0.1027 0.6807 0.041 Uiso 1 1 calc R U . . .
N7A N 0.2668(2) 0.74131(19) 0.89104(19) 0.0180(3) Uani 1 1 d . . . . .
O8A O 0.26724(19) 0.84658(18) 0.83781(18) 0.0250(3) Uani 1 1 d . . . . .
O9A O 0.21106(19) 0.76141(17) 1.01563(17) 0.0235(3) Uani 1 1 d . . . . .
N1B N 0.5617(2) 0.17268(18) 0.33151(18) 0.0161(3) Uani 1 1 d . . . . .
C2B C 0.5852(2) 0.0116(2) 0.2570(2) 0.0171(3) Uani 1 1 d . . . . .
N3B N 0.6525(2) -0.0350(2) 0.1178(2) 0.0191(3) Uani 1 1 d . . . . .
C4B C 0.6739(3) 0.1083(2) 0.1026(2) 0.0202(4) Uani 1 1 d . . . . .
H4B H 0.7188 0.1204 0.0178 0.024 Uiso 1 1 calc R U . . .
C5B C 0.6188(2) 0.2337(2) 0.2320(2) 0.0162(3) Uani 1 1 d . . . . .
C6B C 0.5425(3) -0.1098(2) 0.3216(3) 0.0231(4) Uani 1 1 d . . . . .
H6BA H 0.6292 -0.0841 0.4212 0.035 Uiso 1 1 calc R U . . .
H6BB H 0.5442 -0.2246 0.2374 0.035 Uiso 1 1 calc R U . . .
H6BC H 0.4262 -0.1000 0.3484 0.035 Uiso 1 1 calc R U . . .
N7B N 0.6183(2) 0.40266(19) 0.26329(19) 0.0181(3) Uani 1 1 d . . . . .
O8B O 0.6816(2) 0.44901(18) 0.17192(19) 0.0307(4) Uani 1 1 d . . . . .
O9B O 0.55452(19) 0.49834(17) 0.37862(17) 0.0229(3) Uani 1 1 d . . . . .
N1C N 0.8893(2) -0.45707(18) -0.33094(18) 0.0160(3) Uani 1 1 d . . . . .
C2C C 0.8255(2) -0.3201(2) -0.2415(2) 0.0151(3) Uani 1 1 d . . . . .
N3C N 0.7786(2) -0.32279(19) -0.10602(19) 0.0159(3) Uani 1 1 d . . . . .
H3C H 0.733(3) -0.235(3) -0.025(3) 0.019 Uiso 1 1 d . U . . .
C4C C 0.8116(2) -0.4705(2) -0.1080(2) 0.0158(3) Uani 1 1 d . . . . .
H4C H 0.7922 -0.5101 -0.0310 0.019 Uiso 1 1 calc R U . . .
C5C C 0.8793(2) -0.5494(2) -0.2473(2) 0.0154(3) Uani 1 1 d . . . . .
C6C C 0.8030(3) -0.1773(2) -0.2813(2) 0.0225(4) Uani 1 1 d . . . . .
H6CA H 0.9085 -0.0932 -0.2287 0.034 Uiso 1 1 calc R U . . .
H6CB H 0.7026 -0.1256 -0.2401 0.034 Uiso 1 1 calc R U . . .
H6CC H 0.7831 -0.2192 -0.4012 0.034 Uiso 1 1 calc R U . . .
N7C N 0.9317(2) -0.71205(19) -0.3070(2) 0.0195(3) Uani 1 1 d . . . . .
O8C O 1.00188(19) -0.76202(17) -0.42837(17) 0.0246(3) Uani 1 1 d . . . . .
O9C O 0.9040(2) -0.79655(18) -0.2352(2) 0.0300(3) 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 C2 1.331(2) . ?
N1 C5 1.381(2) . ?
N1 C6 1.473(2) . ?
C2 N3 1.332(2) . ?
C2 H2 0.9500 . ?
N3 C4 1.379(3) . ?
N3 C8 1.465(2) . ?
C4 C5 1.354(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.512(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1A C2A 1.320(2) . ?
N1A C5A 1.362(3) . ?
C2A N3A 1.375(2) . ?
C2A C6A 1.486(3) . ?
N3A C4A 1.358(3) . ?
N3A H3A 0.87(3) . ?
C4A C5A 1.367(3) . ?
C4A H4A 0.9500 . ?
C5A N7A 1.426(2) . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
N7A O9A 1.235(2) . ?
N7A O8A 1.241(2) . ?
N1B C2B 1.336(2) . ?
N1B C5B 1.371(2) . ?
C2B N3B 1.365(2) . ?
C2B C6B 1.496(3) . ?
N3B C4B 1.355(3) . ?
C4B C5B 1.381(3) . ?
C4B H4B 0.9500 . ?
C5B N7B 1.411(2) . ?
C6B H6BA 0.9800 . ?
C6B H6BB 0.9800 . ?
C6B H6BC 0.9800 . ?
N7B O9B 1.236(2) . ?
N7B O8B 1.241(2) . ?
N1C C2C 1.322(2) . ?
N1C C5C 1.365(2) . ?
C2C N3C 1.365(2) . ?
C2C C6C 1.493(2) . ?
N3C C4C 1.358(2) . ?
N3C H3C 0.95(3) . ?
C4C C5C 1.373(3) . ?
C4C H4C 0.9500 . ?
C5C N7C 1.425(2) . ?
C6C H6CA 0.9800 . ?
C6C H6CB 0.9800 . ?
C6C H6CC 0.9800 . ?
N7C O9C 1.235(2) . ?
N7C O8C 1.238(2) . ?

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
C2 N1 C5 109.28(15) . . ?
C2 N1 C6 124.25(16) . . ?
C5 N1 C6 126.40(16) . . ?
N1 C2 N3 108.04(17) . . ?
N1 C2 H2 126.0 . . ?
N3 C2 H2 126.0 . . ?
C2 N3 C4 108.90(17) . . ?
C2 N3 C8 125.31(18) . . ?
C4 N3 C8 125.64(17) . . ?
C5 C4 N3 107.25(18) . . ?
C5 C4 H4 126.4 . . ?
N3 C4 H4 126.4 . . ?
C4 C5 N1 106.52(18) . . ?
C4 C5 H5 126.7 . . ?
N1 C5 H5 126.7 . . ?
N1 C6 C7 112.09(15) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2A N1A C5A 103.42(15) . . ?
N1A C2A N3A 112.03(16) . . ?
N1A C2A C6A 125.29(17) . . ?
N3A C2A C6A 122.67(17) . . ?
C4A N3A C2A 107.26(16) . . ?
C4A N3A H3A 124.9(17) . . ?
C2A N3A H3A 127.9(17) . . ?
N3A C4A C5A 104.35(17) . . ?
N3A C4A H4A 127.8 . . ?
C5A C4A H4A 127.8 . . ?
N1A C5A C4A 112.94(17) . . ?
N1A C5A N7A 121.60(16) . . ?
C4A C5A N7A 125.46(17) . . ?
C2A C6A H6AA 109.5 . . ?
C2A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
C2A C6A H6AC 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
O9A N7A O8A 123.37(16) . . ?
O9A N7A C5A 118.16(15) . . ?
O8A N7A C5A 118.47(16) . . ?
C2B N1B C5B 102.27(15) . . ?
N1B C2B N3B 115.33(16) . . ?
N1B C2B C6B 122.70(16) . . ?
N3B C2B C6B 121.97(16) . . ?
C4B N3B C2B 103.80(15) . . ?
N3B C4B C5B 108.01(16) . . ?
N3B C4B H4B 126.0 . . ?
C5B C4B H4B 126.0 . . ?
N1B C5B C4B 110.59(16) . . ?
N1B C5B N7B 122.64(16) . . ?
C4B C5B N7B 126.77(17) . . ?
C2B C6B H6BA 109.5 . . ?
C2B C6B H6BB 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
C2B C6B H6BC 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
O9B N7B O8B 122.45(16) . . ?
O9B N7B C5B 119.43(15) . . ?
O8B N7B C5B 118.12(16) . . ?
C2C N1C C5C 103.12(15) . . ?
N1C C2C N3C 112.29(16) . . ?
N1C C2C C6C 125.27(16) . . ?
N3C C2C C6C 122.44(16) . . ?
C4C N3C C2C 107.75(15) . . ?
C4C N3C H3C 127.1(14) . . ?
C2C N3C H3C 125.1(14) . . ?
N3C C4C C5C 103.91(15) . . ?
N3C C4C H4C 128.0 . . ?
C5C C4C H4C 128.0 . . ?
N1C C5C C4C 112.93(16) . . ?
N1C C5C N7C 121.08(16) . . ?
C4C C5C N7C 125.97(16) . . ?
C2C C6C H6CA 109.5 . . ?
C2C C6C H6CB 109.5 . . ?
H6CA C6C H6CB 109.5 . . ?
C2C C6C H6CC 109.5 . . ?
H6CA C6C H6CC 109.5 . . ?
H6CB C6C H6CC 109.5 . . ?
O9C N7C O8C 123.21(16) . . ?
O9C N7C C5C 118.21(16) . . ?
O8C N7C C5C 118.58(16) . . ?

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
C5 N1 C2 N3 0.7(2) . . . . ?
C6 N1 C2 N3 -176.39(17) . . . . ?
N1 C2 N3 C4 -0.6(2) . . . . ?
N1 C2 N3 C8 175.15(17) . . . . ?
C2 N3 C4 C5 0.2(2) . . . . ?
C8 N3 C4 C5 -175.50(18) . . . . ?
N3 C4 C5 N1 0.2(2) . . . . ?
C2 N1 C5 C4 -0.6(2) . . . . ?
C6 N1 C5 C4 176.47(17) . . . . ?
C2 N1 C6 C7 -121.9(2) . . . . ?
C5 N1 C6 C7 61.5(2) . . . . ?
C5A N1A C2A N3A -0.1(2) . . . . ?
C5A N1A C2A C6A -178.95(19) . . . . ?
N1A C2A N3A C4A 0.3(2) . . . . ?
C6A C2A N3A C4A 179.21(18) . . . . ?
C2A N3A C4A C5A -0.40(19) . . . . ?
C2A N1A C5A C4A -0.2(2) . . . . ?
C2A N1A C5A N7A 179.09(16) . . . . ?
N3A C4A C5A N1A 0.4(2) . . . . ?
N3A C4A C5A N7A -178.85(16) . . . . ?
N1A C5A N7A O9A -0.9(2) . . . . ?
C4A C5A N7A O9A 178.27(18) . . . . ?
N1A C5A N7A O8A 179.93(18) . . . . ?
C4A C5A N7A O8A -0.9(3) . . . . ?
C5B N1B C2B N3B -0.1(2) . . . . ?
C5B N1B C2B C6B 179.44(17) . . . . ?
N1B C2B N3B C4B 0.1(2) . . . . ?
C6B C2B N3B C4B -179.42(17) . . . . ?
C2B N3B C4B C5B -0.1(2) . . . . ?
C2B N1B C5B C4B 0.0(2) . . . . ?
C2B N1B C5B N7B 179.98(16) . . . . ?
N3B C4B C5B N1B 0.0(2) . . . . ?
N3B C4B C5B N7B -179.92(17) . . . . ?
N1B C5B N7B O9B -4.5(3) . . . . ?
C4B C5B N7B O9B 175.42(18) . . . . ?
N1B C5B N7B O8B 175.96(17) . . . . ?
C4B C5B N7B O8B -4.1(3) . . . . ?
C5C N1C C2C N3C 0.70(19) . . . . ?
C5C N1C C2C C6C -178.50(17) . . . . ?
N1C C2C N3C C4C -0.8(2) . . . . ?
C6C C2C N3C C4C 178.45(17) . . . . ?
C2C N3C C4C C5C 0.47(18) . . . . ?
C2C N1C C5C C4C -0.4(2) . . . . ?
C2C N1C C5C N7C 178.11(16) . . . . ?
N3C C4C C5C N1C -0.1(2) . . . . ?
N3C C4C C5C N7C -178.47(16) . . . . ?
N1C C5C N7C O9C -173.10(17) . . . . ?
C4C C5C N7C O9C 5.2(3) . . . . ?
N1C C5C N7C O8C 6.6(2) . . . . ?
C4C C5C N7C O8C -175.06(17) . . . . ?

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
C2 H2 N1C 0.95 2.46 3.348(2) 155.2 1_477
C2 H2 O8C 0.95 2.47 3.233(2) 137.5 1_477
C5 H5 N1A 0.95 2.53 3.241(3) 131.5 1_565
C5 H5 O9A 0.95 2.47 3.368(2) 157.8 1_565
C7 H7A O9A 0.98 2.63 3.598(3) 167.6 1_565
C7 H7B O8C 0.98 2.60 3.553(2) 165.0 1_487
C7 H7C O8B 0.98 2.57 3.439(3) 148.5 1_466
C8 H8B O9A 0.98 2.55 3.075(2) 113.3 .
C8 H8C O8C 0.98 2.44 3.221(3) 136.0 1_477
N3A H3A N1B 0.87(3) 2.02(3) 2.885(2) 174(2) .
N3A H3A O9B 0.87(3) 2.61(3) 3.047(2) 112(2) .
C4A H4A O9B 0.95 2.39 2.941(2) 116.3 .
N3C H3C N3B 0.95(3) 1.91(3) 2.851(2) 169(2) .
C4C H4C O8B 0.95 2.33 3.253(2) 162.4 1_545

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.045

