# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 1469352'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2017-07-26 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 H8 N4 O2'
_chemical_formula_sum            'C12 H8 N4 O2'
_chemical_formula_weight         240.22

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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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, z+1/2'

_cell_length_a                   4.8736(5)
_cell_length_b                   8.5549(10)
_cell_length_c                   12.5992(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.428(4)
_cell_angle_gamma                90
_cell_volume                     525.14(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2307
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.89

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS (bruekr, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6456
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.381
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2254
_reflns_number_gt                1703
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.976

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_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)+(0.0553P)²] 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_abs_structure_details 
;
 Flack x determined using 697 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2254
_refine_ls_number_parameters     163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.6779(7) 0.6716(4) 0.4358(3) 0.0461(9) Uani 1 1 d . . . . .
H1 H 0.5839 0.7195 0.3794 0.055 Uiso 1 1 calc R U . . .
C2 C 0.8830(8) 0.7513(4) 0.4903(3) 0.0511(9) Uani 1 1 d . . . . .
H2 H 0.9294 0.8527 0.4710 0.061 Uiso 1 1 calc R U . . .
C3 C 1.0169(7) 0.6789(4) 0.5735(3) 0.0486(9) Uani 1 1 d . . . . .
H3 H 1.1560 0.7331 0.6095 0.058 Uiso 1 1 calc R U . . .
C4 C 0.7598(6) 0.4561(3) 0.5521(2) 0.0305(7) Uani 1 1 d . . . . .
C5 C 0.6115(6) 0.5195(4) 0.4650(2) 0.0325(7) Uani 1 1 d . . . . .
C6 C 0.3950(5) 0.4255(4) 0.4122(2) 0.0353(8) Uani 1 1 d . . . . .
C7 C 0.3324(6) 0.2682(4) 0.4536(3) 0.0361(8) Uani 1 1 d . . . . .
C8 C 0.4950(5) 0.2080(4) 0.5453(2) 0.0337(7) Uani 1 1 d . . . . .
C9 C 0.7030(5) 0.2985(4) 0.5909(2) 0.0308(7) Uani 1 1 d . . . . .
C10 C 0.8134(7) 0.1060(4) 0.7114(3) 0.0451(9) Uani 1 1 d . . . . .
H10 H 0.9255 0.0691 0.7668 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6055(8) 0.0113(4) 0.6738(3) 0.0534(10) Uani 1 1 d . . . . .
H11 H 0.5732 -0.0855 0.7046 0.064 Uiso 1 1 calc R U . . .
C12 C 0.4466(7) 0.0628(4) 0.5897(3) 0.0510(10) Uani 1 1 d . . . . .
H12 H 0.3059 0.0001 0.5624 0.061 Uiso 1 1 calc R U . . .
N1 N 0.9581(6) 0.5350(3) 0.6052(2) 0.0426(7) Uani 1 1 d . . . . .
N2 N 0.8630(5) 0.2474(3) 0.6730(2) 0.0391(7) Uani 1 1 d . . . . .
N3 N 0.2429(5) 0.4641(3) 0.3305(2) 0.0462(8) Uani 1 1 d . . . . .
N4 N 0.1432(6) 0.1718(4) 0.4196(2) 0.0507(8) Uani 1 1 d . . . . .
O1 O 0.2846(5) 0.6070(3) 0.2858(2) 0.0622(8) Uani 1 1 d . . . . .
H1A H 0.1999 0.6122 0.2288 0.093 Uiso 1 1 calc R U . . .
O2 O -0.0245(5) 0.2167(3) 0.3358(2) 0.0657(8) Uani 1 1 d . . . . .
H2A H 0.0193 0.3044 0.3162 0.099 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
C1 C2 1.379(5) . ?
C1 C5 1.392(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 N1 1.327(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.344(4) . ?
C4 C5 1.408(4) . ?
C4 C9 1.463(4) . ?
C5 C6 1.472(4) . ?
C6 N3 1.297(4) . ?
C6 C7 1.477(4) . ?
C7 N4 1.302(4) . ?
C7 C8 1.478(4) . ?
C8 C12 1.385(5) . ?
C8 C9 1.389(4) . ?
C9 N2 1.352(4) . ?
C10 N2 1.328(4) . ?
C10 C11 1.373(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N3 O1 1.363(3) . ?
N4 O2 1.374(3) . ?
O1 H1A 0.8200 . ?
O2 H2A 0.8200 . ?

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 C1 C5 120.0(3) . . ?
C2 C1 H1 120.0 . . ?
C5 C1 H1 120.0 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
N1 C3 C2 123.2(3) . . ?
N1 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
N1 C4 C5 122.9(3) . . ?
N1 C4 C9 115.9(3) . . ?
C5 C4 C9 121.2(3) . . ?
C1 C5 C4 116.6(3) . . ?
C1 C5 C6 124.0(3) . . ?
C4 C5 C6 119.3(3) . . ?
N3 C6 C5 127.5(3) . . ?
N3 C6 C7 113.1(3) . . ?
C5 C6 C7 119.4(3) . . ?
N4 C7 C6 127.8(3) . . ?
N4 C7 C8 113.4(3) . . ?
C6 C7 C8 118.8(2) . . ?
C12 C8 C9 117.6(3) . . ?
C12 C8 C7 122.4(3) . . ?
C9 C8 C7 120.0(3) . . ?
N2 C9 C8 122.5(3) . . ?
N2 C9 C4 116.3(2) . . ?
C8 C9 C4 121.2(3) . . ?
N2 C10 C11 123.4(3) . . ?
N2 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C12 C11 C10 118.4(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C8 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C8 C12 H12 119.9 . . ?
C3 N1 C4 118.3(3) . . ?
C10 N2 C9 117.8(3) . . ?
C6 N3 O1 117.9(3) . . ?
C7 N4 O2 118.6(3) . . ?
N3 O1 H1A 109.5 . . ?
N4 O2 H2A 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
C5 C1 C2 C3 -0.5(6) . . . . ?
C1 C2 C3 N1 -0.5(6) . . . . ?
C2 C1 C5 C4 1.0(5) . . . . ?
C2 C1 C5 C6 179.5(3) . . . . ?
N1 C4 C5 C1 -0.6(4) . . . . ?
C9 C4 C5 C1 178.7(3) . . . . ?
N1 C4 C5 C6 -179.2(3) . . . . ?
C9 C4 C5 C6 0.2(4) . . . . ?
C1 C5 C6 N3 2.8(5) . . . . ?
C4 C5 C6 N3 -178.7(3) . . . . ?
C1 C5 C6 C7 -176.8(3) . . . . ?
C4 C5 C6 C7 1.7(4) . . . . ?
N3 C6 C7 N4 -2.2(5) . . . . ?
C5 C6 C7 N4 177.4(3) . . . . ?
N3 C6 C7 C8 178.7(3) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
N4 C7 C8 C12 -0.2(4) . . . . ?
C6 C7 C8 C12 179.0(3) . . . . ?
N4 C7 C8 C9 -179.4(3) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C12 C8 C9 N2 2.6(5) . . . . ?
C7 C8 C9 N2 -178.1(3) . . . . ?
C12 C8 C9 C4 -177.2(3) . . . . ?
C7 C8 C9 C4 2.1(4) . . . . ?
N1 C4 C9 N2 -2.5(4) . . . . ?
C5 C4 C9 N2 178.1(3) . . . . ?
N1 C4 C9 C8 177.3(3) . . . . ?
C5 C4 C9 C8 -2.1(4) . . . . ?
N2 C10 C11 C12 2.4(6) . . . . ?
C10 C11 C12 C8 -0.7(6) . . . . ?
C9 C8 C12 C11 -1.6(5) . . . . ?
C7 C8 C12 C11 179.1(3) . . . . ?
C2 C3 N1 C4 0.9(6) . . . . ?
C5 C4 N1 C3 -0.3(5) . . . . ?
C9 C4 N1 C3 -179.7(3) . . . . ?
C11 C10 N2 C9 -1.5(5) . . . . ?
C8 C9 N2 C10 -1.0(4) . . . . ?
C4 C9 N2 C10 178.8(3) . . . . ?
C5 C6 N3 O1 0.6(5) . . . . ?
C7 C6 N3 O1 -179.8(3) . . . . ?
C6 C7 N4 O2 -0.4(5) . . . . ?
C8 C7 N4 O2 178.7(3) . . . . ?

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
C10 H10 O2 0.93 2.60 3.261(4) 128.1 2_655
O1 H1A N1 0.82 2.30 3.001(4) 143.1 2_464
O1 H1A N2 0.82 2.14 2.765(3) 133.1 2_464
O2 H2A N3 0.82 1.75 2.487(4) 148.0 .

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037

