# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1578001'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2017-10-30 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         'C12 H11 N5 O'
_chemical_formula_sum            'C12 H11 N5 O'
_chemical_formula_weight         241.26

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.97780(10)
_cell_length_b                   12.4862(2)
_cell_length_c                   12.6501(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.808(2)
_cell_angle_gamma                90
_cell_volume                     1099.72(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13842
_cell_measurement_theta_max      32.5320
_cell_measurement_theta_min      3.2200

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.267
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.44a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -8 -3 0.1335
-8 10 -4 0.1928
1 5 -17 0.1569
-1 -5 17 0.1569
-1 -16 -6 0.0761
0 16 -6 0.1470
1 -3 17 0.1571
1 7 16 0.1177


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2303
_diffrn_detector_type            AtlasS2
_diffrn_reflns_number            29046
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_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         2.294
_diffrn_reflns_theta_max         32.960
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3968
_reflns_number_gt                3510
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012) & DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL2014/7 (Sheldrick, 2015)'

_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)+(0.0672P)²+0.3313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3968
_refine_ls_number_parameters     170
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_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
O1 O 0.90967(10) 0.86628(5) 0.52639(5) 0.01952(14) Uani 1 1 d . . . . .
N1 N 0.60370(11) 0.22289(6) 0.74505(5) 0.01498(14) Uani 1 1 d . . . . .
N2 N 0.54536(11) 0.09143(5) 0.60851(5) 0.01318(14) Uani 1 1 d . . . . .
N3 N 0.64399(10) 0.26280(5) 0.56254(5) 0.01096(13) Uani 1 1 d . . . . .
N4 N 0.69564(11) 0.39466(6) 0.68100(5) 0.01415(14) Uani 1 1 d . . . . .
N5 N 0.57872(12) 0.13349(6) 0.43249(6) 0.01492(14) Uani 1 1 d D . . . .
H1N H 0.5452(19) 0.0668(7) 0.4181(10) 0.018 Uiso 1 1 d D U . . .
H2N H 0.5946(19) 0.1822(9) 0.3837(8) 0.018 Uiso 1 1 d D U . . .
C1 C 0.55642(12) 0.12653(7) 0.70967(6) 0.01416(15) Uani 1 1 d . . . . .
H1 H 0.5264 0.0755 0.7618 0.017 Uiso 1 1 calc R U . . .
C2 C 0.58814(11) 0.16090(6) 0.53339(6) 0.01144(14) Uani 1 1 d . . . . .
C4 C 0.69411(12) 0.35232(6) 0.50541(6) 0.01183(14) Uani 1 1 d . . . . .
H4 H 0.7041 0.3575 0.4311 0.014 Uiso 1 1 calc R U . . .
C5 C 0.72601(11) 0.43167(6) 0.57961(6) 0.01206(14) Uani 1 1 d . . . . .
C6 C 0.64726(12) 0.29349(6) 0.66861(6) 0.01254(15) Uani 1 1 d . . . . .
C7 C 0.78360(11) 0.54317(6) 0.56492(6) 0.01232(14) Uani 1 1 d . . . . .
C8 C 0.77261(12) 0.59244(7) 0.46495(6) 0.01359(15) Uani 1 1 d . . . . .
H8 H 0.7340 0.5517 0.4038 0.016 Uiso 1 1 calc R U . . .
C9 C 0.81735(12) 0.69973(7) 0.45450(6) 0.01461(15) Uani 1 1 d . . . . .
H9 H 0.8093 0.7321 0.3864 0.018 Uiso 1 1 calc R U . . .
C10 C 0.87440(12) 0.76064(6) 0.54389(7) 0.01405(15) Uani 1 1 d . . . . .
C11 C 0.89246(13) 0.71232(7) 0.64324(7) 0.01520(15) Uani 1 1 d . . . . .
H11 H 0.9355 0.7526 0.7039 0.018 Uiso 1 1 calc R U . . .
C12 C 0.84679(13) 0.60426(6) 0.65281(7) 0.01471(15) Uani 1 1 d . . . . .
H12 H 0.8589 0.5715 0.7207 0.018 Uiso 1 1 calc R U . . .
C13 C 0.94338(14) 0.93227(7) 0.61833(7) 0.02015(18) Uani 1 1 d . . . . .
H13A H 0.8360 0.9249 0.6639 0.030 Uiso 1 1 calc R U . . .
H13B H 0.9545 1.0072 0.5966 0.030 Uiso 1 1 calc R U . . .
H13C H 1.0627 0.9099 0.6574 0.030 Uiso 1 1 calc R 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
O1 C10 1.3626(10) . ?
O1 C13 1.4319(11) . ?
N1 C1 1.3180(11) . ?
N1 C6 1.3577(10) . ?
N2 C2 1.3350(10) . ?
N2 C1 1.3500(10) . ?
N3 C2 1.3739(10) . ?
N3 C4 1.3884(10) . ?
N3 C6 1.3941(10) . ?
N4 C6 1.3142(10) . ?
N4 C5 1.3927(10) . ?
N5 C2 1.3189(10) . ?
N5 H1N 0.881(8) . ?
N5 H2N 0.879(8) . ?
C1 H1 0.9500 . ?
C4 C5 1.3728(11) . ?
C4 H4 0.9500 . ?
C5 C7 1.4643(11) . ?
C7 C12 1.3955(11) . ?
C7 C8 1.4038(11) . ?
C8 C9 1.3838(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.3985(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.3922(11) . ?
C11 C12 1.3934(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C10 O1 C13 116.53(7) . . ?
C1 N1 C6 114.43(7) . . ?
C2 N2 C1 117.54(7) . . ?
C2 N3 C4 133.05(7) . . ?
C2 N3 C6 119.94(7) . . ?
C4 N3 C6 106.93(6) . . ?
C6 N4 C5 105.23(6) . . ?
C2 N5 H1N 116.2(8) . . ?
C2 N5 H2N 120.0(8) . . ?
H1N N5 H2N 123.6(12) . . ?
N1 C1 N2 127.99(7) . . ?
N1 C1 H1 116.0 . . ?
N2 C1 H1 116.0 . . ?
N5 C2 N2 121.40(7) . . ?
N5 C2 N3 119.68(7) . . ?
N2 C2 N3 118.92(7) . . ?
C5 C4 N3 105.08(6) . . ?
C5 C4 H4 127.5 . . ?
N3 C4 H4 127.5 . . ?
C4 C5 N4 111.25(7) . . ?
C4 C5 C7 129.25(7) . . ?
N4 C5 C7 119.49(7) . . ?
N4 C6 N1 127.37(7) . . ?
N4 C6 N3 111.50(7) . . ?
N1 C6 N3 121.12(7) . . ?
C12 C7 C8 118.27(7) . . ?
C12 C7 C5 119.56(7) . . ?
C8 C7 C5 122.14(7) . . ?
C9 C8 C7 120.74(7) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.21(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
O1 C10 C11 124.04(8) . . ?
O1 C10 C9 116.09(7) . . ?
C11 C10 C9 119.87(7) . . ?
C10 C11 C12 119.38(8) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 121.47(7) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C6 N1 C1 N2 -0.55(13) . . . . ?
C2 N2 C1 N1 0.54(13) . . . . ?
C1 N2 C2 N5 -179.17(8) . . . . ?
C1 N2 C2 N3 1.17(11) . . . . ?
C4 N3 C2 N5 1.47(13) . . . . ?
C6 N3 C2 N5 177.58(7) . . . . ?
C4 N3 C2 N2 -178.86(8) . . . . ?
C6 N3 C2 N2 -2.75(11) . . . . ?
C2 N3 C4 C5 176.85(8) . . . . ?
C6 N3 C4 C5 0.38(9) . . . . ?
N3 C4 C5 N4 -0.55(9) . . . . ?
N3 C4 C5 C7 179.72(8) . . . . ?
C6 N4 C5 C4 0.50(10) . . . . ?
C6 N4 C5 C7 -179.74(7) . . . . ?
C5 N4 C6 N1 179.87(8) . . . . ?
C5 N4 C6 N3 -0.25(9) . . . . ?
C1 N1 C6 N4 178.75(9) . . . . ?
C1 N1 C6 N3 -1.13(12) . . . . ?
C2 N3 C6 N4 -177.11(7) . . . . ?
C4 N3 C6 N4 -0.08(9) . . . . ?
C2 N3 C6 N1 2.78(12) . . . . ?
C4 N3 C6 N1 179.81(8) . . . . ?
C4 C5 C7 C12 -166.68(8) . . . . ?
N4 C5 C7 C12 13.60(11) . . . . ?
C4 C5 C7 C8 15.11(13) . . . . ?
N4 C5 C7 C8 -164.60(8) . . . . ?
C12 C7 C8 C9 -2.08(12) . . . . ?
C5 C7 C8 C9 176.15(8) . . . . ?
C7 C8 C9 C10 0.02(13) . . . . ?
C13 O1 C10 C11 -8.13(12) . . . . ?
C13 O1 C10 C9 172.03(8) . . . . ?
C8 C9 C10 O1 -177.99(8) . . . . ?
C8 C9 C10 C11 2.17(13) . . . . ?
O1 C10 C11 C12 177.94(8) . . . . ?
C9 C10 C11 C12 -2.23(13) . . . . ?
C8 C7 C12 C11 2.01(12) . . . . ?
C5 C7 C12 C11 -176.27(8) . . . . ?
C10 C11 C12 C7 0.13(13) . . . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.066

