# 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. 
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data_A5AP_Me
_database_code_depnum_ccdc_archive 'CCDC 1533266'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N6'
_chemical_formula_sum            'C11 H12 N6'
_chemical_formula_weight         228.27

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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   14.892(5)
_cell_length_b                   6.4795(19)
_cell_length_c                   10.752(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1037.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    4894
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.74

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3544
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed Xray tube'
_diffrn_measurement_device_type  'Rigaku R-AXISIP'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            8762
_diffrn_reflns_av_unetI/netI     0.2163
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.328
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1292
_reflns_number_gt                936
_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       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0660P)²+0.4742P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1292
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.44057(16) 0.2500 0.4175(2) 0.0243(5) Uani 1 2 d S T P . .
N2 N 0.49514(15) 0.2500 0.6249(2) 0.0226(6) Uani 1 2 d S T P . .
N3 N 0.39075(15) 0.2500 0.7916(2) 0.0250(6) Uani 1 2 d S T P . .
N4 N 0.33793(15) 0.2500 0.5908(2) 0.0228(5) Uani 1 2 d S T P . .
N5 N 0.54798(16) 0.2500 0.8334(2) 0.0258(6) Uani 1 2 d S T P . .
N6 N 0.28874(15) 0.2500 0.3882(2) 0.0248(6) Uani 1 2 d S T P . .
C1 C 0.40576(19) 0.2500 0.6683(2) 0.0220(6) Uani 1 2 d S T P . .
C2 C 0.35792(19) 0.2500 0.4668(3) 0.0231(6) Uani 1 2 d S T P . .
C3 C 0.56598(18) 0.2500 0.7099(3) 0.0239(6) Uani 1 2 d S T P . .
C4 C 0.5982(2) 0.2500 0.4558(3) 0.0270(7) Uani 1 2 d S T P . .
H1 H 0.6107 0.2500 0.3691 0.032 Uiso 1 2 calc R U P . .
C5 C 0.50928(19) 0.2500 0.4962(3) 0.0228(6) Uani 1 2 d S T P . .
C6 C 0.65254(19) 0.2500 0.6657(3) 0.0254(7) Uani 1 2 d S T P . .
H2 H 0.7017 0.2500 0.7220 0.031 Uiso 1 2 calc R U P . .
C7 C 0.4630(2) 0.2500 0.8661(3) 0.0245(7) Uani 1 2 d S T P . .
C8 C 0.6679(2) 0.2500 0.5389(3) 0.0272(7) Uani 1 2 d S T P . .
H3 H 0.7279 0.2500 0.5089 0.033 Uiso 1 2 calc R U P . .
C9 C 0.4434(2) 0.2500 1.0027(2) 0.0270(7) Uani 1 2 d S T P . .
H4 H 0.4189 0.1155 1.0269 0.040 Uiso 0.5 1 calc R U P . .
H5 H 0.3995 0.3583 1.0216 0.040 Uiso 0.5 1 calc R U P . .
H6 H 0.4989 0.2762 1.0490 0.040 Uiso 0.5 1 calc R U P . .
C10 C 0.19562(18) 0.2500 0.4271(3) 0.0286(7) Uani 1 2 d S T P . .
H7 H 0.1923 0.2280 0.5172 0.043 Uiso 0.5 1 calc R U P . .
H8 H 0.1634 0.1390 0.3843 0.043 Uiso 0.5 1 calc R U P . .
H9 H 0.1682 0.3830 0.4062 0.043 Uiso 0.5 1 calc R U P . .
C11 C 0.3012(2) 0.2500 0.2544(2) 0.0304(7) Uani 1 2 d S T P . .
H10 H 0.3646 0.2755 0.2350 0.046 Uiso 0.5 1 calc R U P . .
H11 H 0.2642 0.3588 0.2171 0.046 Uiso 0.5 1 calc R U P . .
H12 H 0.2833 0.1158 0.2205 0.046 Uiso 0.5 1 calc R U P . .


_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 C5 1.328(4) . ?
N1 C2 1.340(3) . ?
N2 C3 1.396(3) . ?
N2 C5 1.399(4) . ?
N2 C1 1.410(3) . ?
N3 C7 1.342(4) . ?
N3 C1 1.344(3) . ?
N4 C1 1.310(3) . ?
N4 C2 1.365(3) . ?
N5 C7 1.313(4) . ?
N5 C3 1.354(4) . ?
N6 C2 1.333(3) . ?
N6 C10 1.449(3) . ?
N6 C11 1.451(3) . ?
C3 C6 1.374(4) . ?
C4 C8 1.370(4) . ?
C4 C5 1.394(4) . ?
C4 H1 0.9500 . ?
C6 C8 1.382(4) . ?
C6 H2 0.9500 . ?
C7 C9 1.498(4) . ?
C8 H3 0.9500 . ?
C9 H4 0.9800 . ?
C9 H5 0.9800 . ?
C9 H6 0.9800 . ?
C10 H7 0.9800 . ?
C10 H8 0.9800 . ?
C10 H9 0.9800 . ?
C11 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 H12 0.9800 . ?

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
C5 N1 C2 117.1(2) . . ?
C3 N2 C5 122.3(2) . . ?
C3 N2 C1 119.7(2) . . ?
C5 N2 C1 118.0(2) . . ?
C7 N3 C1 117.1(2) . . ?
C1 N4 C2 117.0(2) . . ?
C7 N5 C3 116.9(2) . . ?
C2 N6 C10 123.8(2) . . ?
C2 N6 C11 122.0(2) . . ?
C10 N6 C11 114.1(2) . . ?
N4 C1 N3 120.0(3) . . ?
N4 C1 N2 121.1(2) . . ?
N3 C1 N2 118.9(2) . . ?
N6 C2 N1 117.3(2) . . ?
N6 C2 N4 116.8(2) . . ?
N1 C2 N4 125.9(3) . . ?
N5 C3 C6 121.7(3) . . ?
N5 C3 N2 119.5(2) . . ?
C6 C3 N2 118.8(3) . . ?
C8 C4 C5 121.0(3) . . ?
C8 C4 H1 119.5 . . ?
C5 C4 H1 119.5 . . ?
N1 C5 C4 122.2(3) . . ?
N1 C5 N2 120.9(2) . . ?
C4 C5 N2 116.8(3) . . ?
C3 C6 C8 119.8(3) . . ?
C3 C6 H2 120.1 . . ?
C8 C6 H2 120.1 . . ?
N5 C7 N3 127.8(2) . . ?
N5 C7 C9 116.8(3) . . ?
N3 C7 C9 115.4(2) . . ?
C4 C8 C6 121.2(3) . . ?
C4 C8 H3 119.4 . . ?
C6 C8 H3 119.4 . . ?
C7 C9 H4 109.5 . . ?
C7 C9 H5 109.5 . . ?
H4 C9 H5 109.5 . . ?
C7 C9 H6 109.5 . . ?
H4 C9 H6 109.5 . . ?
H5 C9 H6 109.5 . . ?
N6 C10 H7 109.5 . . ?
N6 C10 H8 109.5 . . ?
H7 C10 H8 109.5 . . ?
N6 C10 H9 109.5 . . ?
H7 C10 H9 109.5 . . ?
H8 C10 H9 109.5 . . ?
N6 C11 H10 109.5 . . ?
N6 C11 H11 109.5 . . ?
H10 C11 H11 109.5 . . ?
N6 C11 H12 109.5 . . ?
H10 C11 H12 109.5 . . ?
H11 C11 H12 109.5 . . ?

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
C2 N4 C1 N3 180.000(0) . . . . ?
C2 N4 C1 N2 0.000(0) . . . . ?
C7 N3 C1 N4 180.000(0) . . . . ?
C7 N3 C1 N2 0.000(1) . . . . ?
C3 N2 C1 N4 180.000(0) . . . . ?
C5 N2 C1 N4 0.000(1) . . . . ?
C3 N2 C1 N3 0.000(1) . . . . ?
C5 N2 C1 N3 180.000(0) . . . . ?
C10 N6 C2 N1 180.000(0) . . . . ?
C11 N6 C2 N1 0.000(0) . . . . ?
C10 N6 C2 N4 0.000(0) . . . . ?
C11 N6 C2 N4 180.000(0) . . . . ?
C5 N1 C2 N6 180.000(0) . . . . ?
C5 N1 C2 N4 0.000(0) . . . . ?
C1 N4 C2 N6 180.000(0) . . . . ?
C1 N4 C2 N1 0.000(0) . . . . ?
C7 N5 C3 C6 180.000(1) . . . . ?
C7 N5 C3 N2 0.000(1) . . . . ?
C5 N2 C3 N5 180.000(0) . . . . ?
C1 N2 C3 N5 0.000(1) . . . . ?
C5 N2 C3 C6 0.000(1) . . . . ?
C1 N2 C3 C6 180.000(0) . . . . ?
C2 N1 C5 C4 180.000(0) . . . . ?
C2 N1 C5 N2 0.000(0) . . . . ?
C8 C4 C5 N1 180.000(0) . . . . ?
C8 C4 C5 N2 0.000(0) . . . . ?
C3 N2 C5 N1 180.000(0) . . . . ?
C1 N2 C5 N1 0.000(0) . . . . ?
C3 N2 C5 C4 0.000(1) . . . . ?
C1 N2 C5 C4 180.000(0) . . . . ?
N5 C3 C6 C8 180.000(1) . . . . ?
N2 C3 C6 C8 0.000(1) . . . . ?
C3 N5 C7 N3 0.000(1) . . . . ?
C3 N5 C7 C9 180.000(1) . . . . ?
C1 N3 C7 N5 0.000(1) . . . . ?
C1 N3 C7 C9 180.000(1) . . . . ?
C5 C4 C8 C6 0.000(1) . . . . ?
C3 C6 C8 C4 0.000(1) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.079

