# Electronic Supplementary Material (ESI) for Analyst.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 980609'
_audit_update_record             
;
2014-01-08 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N5 O2'
_chemical_formula_sum            'C13 H9 N5 O2'
_chemical_formula_weight         267.25

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  -P2ybc

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

_cell_length_a                   3.8512(6)
_cell_length_b                   19.078(3)
_cell_length_c                   21.230(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.015(4)
_cell_angle_gamma                90.00
_cell_volume                     1559.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4550
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         24.86
_reflns_number_total             2718
_reflns_number_gt                1529
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1307P)²+1.0318P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     181
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.2442
_refine_ls_wR_factor_gt          0.2212
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.076
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4286(7) 0.72627(16) -0.02791(13) 0.0584(9) Uani 1 1 d U . .
N4 N 1.1019(7) 0.30488(18) 0.15171(13) 0.0402(8) Uani 1 1 d U . .
N5 N 0.6278(9) 0.73404(19) 0.01691(15) 0.0476(9) Uani 1 1 d U . .
N3 N 0.9980(8) 0.16826(18) 0.10991(14) 0.0493(9) Uani 1 1 d U . .
H3A H 0.9044 0.2026 0.0877 0.059 Uiso 1 1 calc R . .
H3B H 0.9709 0.1246 0.0975 0.059 Uiso 1 1 calc R . .
O2 O 0.7328(11) 0.79106(17) 0.03361(15) 0.0831(11) Uani 1 1 d U . .
C13 C 1.0205(9) 0.6210(2) 0.14003(16) 0.0381(9) Uani 1 1 d U . .
H13 H 1.1380 0.6256 0.1795 0.046 Uiso 1 1 calc R . .
C8 C 0.9547(8) 0.5544(2) 0.11612(16) 0.0355(9) Uani 1 1 d U . .
C11 C 0.7497(9) 0.67255(19) 0.05133(16) 0.0361(9) Uani 1 1 d U . .
C6 C 1.0187(9) 0.4260(2) 0.13599(17) 0.0386(9) Uani 1 1 d U . .
H6 H 0.8833 0.4166 0.0991 0.046 Uiso 1 1 calc R . .
N2 N 1.5768(9) 0.2714(2) 0.28887(17) 0.0587(11) Uani 1 1 d U . .
C4 C 1.2382(9) 0.2481(2) 0.18548(17) 0.0401(9) Uani 1 1 d U . .
C10 C 0.6802(9) 0.6070(2) 0.02544(17) 0.0399(9) Uani 1 1 d U . .
H10 H 0.5630 0.6028 -0.0141 0.048 Uiso 1 1 calc R . .
N1 N 1.4366(10) 0.0773(2) 0.22361(17) 0.0602(11) Uani 1 1 d U . .
C7 C 1.0736(9) 0.4925(2) 0.15181(16) 0.0393(10) Uani 1 1 d U . .
H7 H 1.2017 0.5009 0.1897 0.047 Uiso 1 1 calc R . .
C12 C 0.9206(10) 0.6798(2) 0.10816(17) 0.0430(10) Uani 1 1 d U . .
H12 H 0.9684 0.7250 0.1250 0.052 Uiso 1 1 calc R . .
C3 C 1.1809(9) 0.1825(2) 0.16227(17) 0.0420(10) Uani 1 1 d U . .
C9 C 0.7840(9) 0.5488(2) 0.05806(17) 0.0389(9) Uani 1 1 d U . .
H9 H 0.7388 0.5037 0.0408 0.047 Uiso 1 1 calc R . .
C5 C 1.1517(9) 0.3675(2) 0.17127(17) 0.0399(10) Uani 1 1 d U . .
H5 H 1.2778 0.3753 0.2095 0.048 Uiso 1 1 calc R . .
C2 C 1.4268(9) 0.2579(2) 0.24317(19) 0.0423(10) Uani 1 1 d U . .
C1 C 1.3254(10) 0.1235(2) 0.19582(18) 0.0464(11) Uani 1 1 d U . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0560(18) 0.064(2) 0.0548(18) 0.0159(14) -0.0120(14) 0.0014(15)
N4 0.0349(17) 0.046(2) 0.0398(18) 0.0073(15) -0.0022(13) 0.0046(15)
N5 0.048(2) 0.049(2) 0.0455(19) 0.0028(17) 0.0057(16) 0.0015(17)
N3 0.058(2) 0.044(2) 0.0451(19) 0.0039(15) -0.0046(16) 0.0062(16)
O2 0.134(3) 0.039(2) 0.075(2) 0.0014(17) -0.025(2) -0.007(2)
C13 0.035(2) 0.047(2) 0.0317(19) 0.0003(17) -0.0061(15) -0.0029(18)
C8 0.0236(18) 0.047(2) 0.036(2) 0.0027(17) 0.0009(15) -0.0014(16)
C11 0.031(2) 0.038(2) 0.038(2) 0.0077(17) 0.0007(15) -0.0044(17)
C6 0.0291(19) 0.051(3) 0.036(2) 0.0038(19) -0.0024(15) 0.0014(18)
N2 0.045(2) 0.081(3) 0.051(2) 0.014(2) -0.0048(17) 0.0042(18)
C4 0.0281(19) 0.051(2) 0.041(2) 0.0103(19) 0.0014(15) 0.0072(18)
C10 0.034(2) 0.051(2) 0.035(2) 0.0017(19) -0.0057(15) -0.0074(18)
N1 0.061(2) 0.061(3) 0.058(2) 0.0125(19) -0.0038(18) 0.0112(19)
C7 0.031(2) 0.052(3) 0.035(2) 0.0045(18) -0.0011(15) -0.0011(18)
C12 0.044(2) 0.044(2) 0.041(2) -0.0077(18) -0.0034(17) -0.0038(18)
C3 0.037(2) 0.050(3) 0.039(2) 0.0078(18) 0.0054(17) 0.0088(19)
C9 0.035(2) 0.037(2) 0.044(2) -0.0003(17) -0.0038(16) -0.0030(17)
C5 0.029(2) 0.054(3) 0.036(2) 0.0078(19) -0.0021(15) 0.0012(18)
C2 0.032(2) 0.053(3) 0.041(2) 0.0107(19) 0.0056(17) 0.0067(18)
C1 0.045(2) 0.049(3) 0.045(2) 0.009(2) 0.0042(18) 0.008(2)

_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 N5 1.221(4) . ?
N4 C5 1.278(5) . ?
N4 C4 1.396(5) . ?
N5 O2 1.211(4) . ?
N5 C11 1.455(5) . ?
N3 C3 1.333(5) . ?
C13 C12 1.363(5) . ?
C13 C8 1.389(5) . ?
C8 C9 1.391(5) . ?
C8 C7 1.472(5) . ?
C11 C12 1.371(5) . ?
C11 C10 1.390(5) . ?
C6 C7 1.330(5) . ?
C6 C5 1.433(5) . ?
N2 C2 1.150(5) . ?
C4 C3 1.362(5) . ?
C4 C2 1.425(6) . ?
C10 C9 1.365(5) . ?
N1 C1 1.141(5) . ?
C3 C1 1.437(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
C5 N4 C4 120.4(3) . . ?
O2 N5 O1 122.6(4) . . ?
O2 N5 C11 118.3(3) . . ?
O1 N5 C11 119.1(4) . . ?
C12 C13 C8 121.6(3) . . ?
C13 C8 C9 118.4(3) . . ?
C13 C8 C7 119.5(3) . . ?
C9 C8 C7 122.1(4) . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 N5 120.4(3) . . ?
C10 C11 N5 117.9(3) . . ?
C7 C6 C5 123.9(4) . . ?
C3 C4 N4 118.1(3) . . ?
C3 C4 C2 120.6(3) . . ?
N4 C4 C2 121.4(4) . . ?
C9 C10 C11 118.6(3) . . ?
C6 C7 C8 126.1(3) . . ?
C13 C12 C11 118.7(4) . . ?
N3 C3 C4 124.6(3) . . ?
N3 C3 C1 116.7(4) . . ?
C4 C3 C1 118.7(3) . . ?
C10 C9 C8 121.0(4) . . ?
N4 C5 C6 120.5(3) . . ?
N2 C2 C4 174.6(4) . . ?
N1 C1 C3 178.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        24.86
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.066
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.077 0.000 0.000 187 29 ' '
2 -0.123 0.500 0.500 187 29 ' '
_platon_squeeze_details          
;
;

