# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 1914948'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro, CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

#=============================================================================
_audit_creation_method           'SHELXL-2018/3, manual editing plus enCIFer'
_audit_creation_date             '08 May 2019'
_shelx_SHELXL_version_number     2018/3
#=============================================================================


_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N4 O2'
_chemical_formula_sum            'C10 H8 N4 O2'
_chemical_formula_weight         216.20

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.0748(4)
_cell_length_b                   8.1131(4)
_cell_length_c                   16.9559(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     973.24(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1450
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      25.30

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   0.7013
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
  SADABS-2016/2
  Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  J. Appl. Cryst. 48 (2015) 3-10.
;

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3251
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.751
_diffrn_reflns_theta_max         25.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1736
_reflns_number_gt                1595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.959

_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 2012.4 (Bruker, 2012b)'
_computing_cell_refinement       'SAINT V8.27b (Bruker, 2012a)'
_computing_data_reduction        'SAINT V8.27b (Bruker, 2012a)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.0491P)²+0.1516P] 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 581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1736
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 0.7121(3) 0.1433(3) 0.33726(13) 0.0362(5) Uani 1 1 d . . . . .
O2 O 0.9217(3) 0.2910(3) 0.27749(11) 0.0359(5) Uani 1 1 d . . . . .
N1 N 0.4392(3) 0.1760(3) 0.52519(14) 0.0311(6) Uani 1 1 d . . . . .
N2 N 0.7709(3) 0.2770(3) 0.31291(12) 0.0240(5) Uani 1 1 d . . . . .
N3 N 0.3714(3) 0.8539(3) 0.37346(13) 0.0229(5) Uani 1 1 d . . . . .
N4 N 0.2125(3) 0.7830(3) 0.40289(12) 0.0221(5) Uani 1 1 d . . . . .
C1 C 0.4087(3) 0.2123(3) 0.46107(15) 0.0212(6) Uani 1 1 d . . . . .
C2 C 0.3672(4) 0.2633(3) 0.38011(14) 0.0200(6) Uani 1 1 d . . . . .
H2A H 0.230121 0.284873 0.374754 0.024 Uiso 1 1 calc R U . . .
H2B H 0.400970 0.173043 0.343420 0.024 Uiso 1 1 calc R U . . .
C3 C 0.4771(3) 0.4178(3) 0.35809(13) 0.0171(5) Uani 1 1 d . . . . .
C4 C 0.6589(3) 0.4266(3) 0.32731(14) 0.0191(6) Uani 1 1 d . . . . .
C5 C 0.7494(3) 0.5775(3) 0.30838(14) 0.0218(6) Uani 1 1 d . . . . .
H5 H 0.872753 0.575001 0.286270 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6643(3) 0.7260(3) 0.32102(14) 0.0223(6) Uani 1 1 d . . . . .
H6 H 0.725753 0.826559 0.308125 0.027 Uiso 1 1 calc R U . . .
C7 C 0.4809(3) 0.7241(3) 0.35414(13) 0.0191(5) Uani 1 1 d . . . . .
C8 C 0.3896(3) 0.5717(3) 0.37103(13) 0.0176(5) Uani 1 1 d . . . . .
C9 C 0.2146(4) 0.6182(3) 0.40272(14) 0.0196(6) Uani 1 1 d . . . . .
H9 H 0.116975 0.546861 0.420519 0.023 Uiso 1 1 calc R U . . .
C10 C 0.0611(4) 0.8888(4) 0.43092(18) 0.0311(7) Uani 1 1 d . . . . .
H10A H 0.087246 1.003085 0.415673 0.047 Uiso 0.5 1 calc R U P . .
H10B H 0.052718 0.881286 0.488502 0.047 Uiso 0.5 1 calc R U P . .
H10C H -0.058918 0.853515 0.407498 0.047 Uiso 0.5 1 calc R U P . .
H10D H -0.033215 0.822173 0.458775 0.047 Uiso 0.5 1 calc R U P . .
H10E H 0.001312 0.943971 0.385946 0.047 Uiso 0.5 1 calc R U P . .
H10F H 0.112949 0.971742 0.466951 0.047 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
O1 N2 1.233(3) . ?
O2 N2 1.230(3) . ?
N1 C1 1.147(3) . ?
N2 C4 1.469(3) . ?
N3 C7 1.348(3) . ?
N3 N4 1.358(3) . ?
N4 C9 1.337(3) . ?
N4 C10 1.453(3) . ?
C1 C2 1.463(4) . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.390(3) . ?
C3 C8 1.410(4) . ?
C4 C5 1.418(4) . ?
C5 C6 1.364(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.424(4) . ?
C8 C9 1.401(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 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
O2 N2 O1 122.5(2) . . ?
O2 N2 C4 118.2(2) . . ?
O1 N2 C4 119.3(2) . . ?
C7 N3 N4 103.5(2) . . ?
C9 N4 N3 114.5(2) . . ?
C9 N4 C10 126.8(2) . . ?
N3 N4 C10 118.7(2) . . ?
N1 C1 C2 178.3(3) . . ?
C1 C2 C3 111.1(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C8 114.8(2) . . ?
C4 C3 C2 127.3(2) . . ?
C8 C3 C2 117.8(2) . . ?
C3 C4 C5 123.1(2) . . ?
C3 C4 N2 121.3(2) . . ?
C5 C4 N2 115.6(2) . . ?
C6 C5 C4 121.9(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 117.2(2) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
N3 C7 C6 128.0(2) . . ?
N3 C7 C8 111.7(2) . . ?
C6 C7 C8 120.4(2) . . ?
C9 C8 C3 133.3(2) . . ?
C9 C8 C7 104.1(2) . . ?
C3 C8 C7 122.5(2) . . ?
N4 C9 C8 106.2(2) . . ?
N4 C9 H9 126.9 . . ?
C8 C9 H9 126.9 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
N4 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
N4 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 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
C7 N3 N4 C9 -0.5(3) . . . . ?
C7 N3 N4 C10 179.4(2) . . . . ?
C1 C2 C3 C4 87.1(3) . . . . ?
C1 C2 C3 C8 -91.6(3) . . . . ?
C8 C3 C4 C5 -1.4(3) . . . . ?
C2 C3 C4 C5 179.8(2) . . . . ?
C8 C3 C4 N2 178.0(2) . . . . ?
C2 C3 C4 N2 -0.7(4) . . . . ?
O2 N2 C4 C3 171.9(2) . . . . ?
O1 N2 C4 C3 -8.8(3) . . . . ?
O2 N2 C4 C5 -8.6(3) . . . . ?
O1 N2 C4 C5 170.6(2) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
N2 C4 C5 C6 -177.9(2) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
N4 N3 C7 C6 -179.6(2) . . . . ?
N4 N3 C7 C8 0.4(3) . . . . ?
C5 C6 C7 N3 178.4(2) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
C4 C3 C8 C9 -177.6(2) . . . . ?
C2 C3 C8 C9 1.3(4) . . . . ?
C4 C3 C8 C7 -0.2(3) . . . . ?
C2 C3 C8 C7 178.7(2) . . . . ?
N3 C7 C8 C9 -0.2(3) . . . . ?
C6 C7 C8 C9 179.8(2) . . . . ?
N3 C7 C8 C3 -178.2(2) . . . . ?
C6 C7 C8 C3 1.8(3) . . . . ?
N3 N4 C9 C8 0.4(3) . . . . ?
C10 N4 C9 C8 -179.5(2) . . . . ?
C3 C8 C9 N4 177.6(2) . . . . ?
C7 C8 C9 N4 -0.1(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
_geom_hbond_publ_flag
C2 H2A N1 0.99 2.69 3.463(3) 135.6 4_456 yes
C2 H2B O1 0.99 2.22 2.725(3) 110.4 . yes
C2 H2B N3 0.99 2.65 3.323(3) 125.7 1_545 yes
C5 H5 O2 0.95 2.52 3.246(3) 133.2 3_755 yes
C6 H6 O1 0.95 2.62 3.414(3) 141.5 1_565 yes
C9 H9 N1 0.95 2.39 3.314(3) 165.2 4_456 yes

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1914950'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro, CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

#=============================================================================
_audit_creation_method           'SHELXL-2018/3, manual editing plus enCIFer'
_audit_creation_date             '08 May 2019'
_shelx_SHELXL_version_number     2018/3
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N4 O2'
_chemical_formula_sum            'C10 H8 N4 O2'
_chemical_formula_weight         216.20

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

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

_cell_length_a                   6.5388(7)
_cell_length_b                   18.888(2)
_cell_length_c                   15.6064(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1927.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5670
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.38

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   0.6727
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
  SADABS-2016/2
  Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  J. Appl. Cryst. 48 (2015) 3-10.
;

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9213
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.546
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             962
_reflns_number_gt                891
_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       'APEX2 2012.4 (Bruker, 2012b)'
_computing_cell_refinement       'SAINT V8.27b (Bruker, 2012a)'
_computing_data_reduction        'SAINT V8.27b (Bruker, 2012a)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.0465P)²+1.6229P] 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         962
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 0.500000 0.63861(9) 0.67552(11) 0.0247(4) Uani 1 2 d S T P . .
H1 H 0.500000 0.642196 0.736234 0.030 Uiso 1 2 calc R U P . .
C2 C 0.500000 0.69452(9) 0.61689(10) 0.0221(4) Uani 1 2 d S T P . .
C3 C 0.500000 0.66000(9) 0.53580(10) 0.0227(4) Uani 1 2 d S T P . .
C4 C 0.500000 0.69932(9) 0.45919(10) 0.0236(4) Uani 1 2 d S T P . .
H4 H 0.500000 0.676149 0.405158 0.028 Uiso 1 2 calc R U P . .
C5 C 0.500000 0.77132(9) 0.46421(10) 0.0227(4) Uani 1 2 d S T P . .
H5 H 0.500000 0.797793 0.412454 0.027 Uiso 1 2 calc R U P . .
C6 C 0.500000 0.80877(9) 0.54344(10) 0.0225(4) Uani 1 2 d S T P . .
C7 C 0.500000 0.76972(9) 0.61879(10) 0.0228(4) Uani 1 2 d S T P . .
C8 C 0.500000 0.88942(10) 0.54129(11) 0.0278(4) Uani 1 2 d S T P . .
H8A H 0.377724 0.906963 0.572087 0.033 Uiso 0.5 1 calc R U P . .
H8B H 0.622276 0.906963 0.572087 0.033 Uiso 0.5 1 calc R U P . .
C9 C 0.500000 0.91870(9) 0.45410(12) 0.0281(4) Uani 1 2 d S T P . .
C10 C 0.500000 0.50657(9) 0.66239(12) 0.0337(5) Uani 1 2 d S T P . .
H10A H 0.636511 0.494912 0.684137 0.051 Uiso 0.25 1 calc R U P . .
H10B H 0.463342 0.473561 0.616437 0.051 Uiso 0.25 1 calc R U P . .
H10C H 0.400147 0.502751 0.708990 0.051 Uiso 0.25 1 calc R U P . .
H10D H 0.363489 0.485904 0.655573 0.051 Uiso 0.25 1 calc R U P . .
H10E H 0.536658 0.507255 0.723272 0.051 Uiso 0.25 1 calc R U P . .
H10F H 0.599853 0.478065 0.630719 0.051 Uiso 0.25 1 calc R U P . .
N1 N 0.500000 0.57884(7) 0.62901(9) 0.0251(4) Uani 1 2 d S T P . .
N2 N 0.500000 0.58884(8) 0.54357(9) 0.0263(4) Uani 1 2 d S T P . .
N3 N 0.500000 0.80331(8) 0.70290(9) 0.0304(4) Uani 1 2 d S T P . .
N4 N 0.500000 0.94259(8) 0.38657(11) 0.0363(4) Uani 1 2 d S T P . .
O1 O 0.500000 0.76513(8) 0.76502(9) 0.0690(6) Uani 1 2 d S T P . .
O2 O 0.500000 0.86727(8) 0.70963(9) 0.0606(6) Uani 1 2 d S T 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
C1 N1 1.342(2) . ?
C1 C2 1.397(2) . ?
C1 H1 0.9500 . ?
C2 C7 1.421(2) . ?
C2 C3 1.424(2) . ?
C3 N2 1.350(2) . ?
C3 C4 1.408(2) . ?
C4 C5 1.362(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.425(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 C8 1.524(2) . ?
C7 N3 1.458(2) . ?
C8 C9 1.469(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N4 1.147(2) . ?
C10 N1 1.461(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C10 H10A 0.98(2) 12_655 ?
C10 H10B 0.98(2) 12_655 ?
C10 H10C 0.98(5) 12_655 ?
C10 H10D 0.98(2) 12_655 ?
C10 H10E 0.98(2) 12_655 ?
C10 H10F 0.98(5) 12_655 ?
N1 N2 1.3467(19) . ?
N3 O1 1.208(2) . ?
N3 O2 1.213(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
N1 C1 C2 106.35(14) . . ?
N1 C1 H1 126.8 . . ?
C2 C1 H1 126.8 . . ?
C1 C2 C7 137.89(15) . . ?
C1 C2 C3 103.65(15) . . ?
C7 C2 C3 118.45(15) . . ?
N2 C3 C4 127.00(15) . . ?
N2 C3 C2 112.11(15) . . ?
C4 C3 C2 120.90(16) . . ?
C5 C4 C3 118.55(15) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 123.07(15) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C7 C6 C5 118.13(15) . . ?
C7 C6 C8 123.36(14) . . ?
C5 C6 C8 118.51(14) . . ?
C6 C7 C2 120.90(14) . . ?
C6 C7 N3 122.11(15) . . ?
C2 C7 N3 116.99(14) . . ?
C9 C8 C6 113.38(14) . . ?
C9 C8 H8A 108.9 . . ?
C6 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C6 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
N4 C9 C8 178.93(19) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
N1 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
N1 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
N1 C10 H10A 109.5(5) . 12_655 ?
H10A C10 H10A 131.2 . 12_655 ?
H10B C10 H10A 83.6 . 12_655 ?
H10C C10 H10A 28.3 . 12_655 ?
H10D C10 H10A 28.2 . 12_655 ?
H10E C10 H10A 83.7 . 12_655 ?
H10F C10 H10A 131.2 . 12_655 ?
N1 C10 H10B 109.5(5) . 12_655 ?
H10A C10 H10B 83.6 . 12_655 ?
H10B C10 H10B 28.3 . 12_655 ?
H10C C10 H10B 131.2 . 12_655 ?
H10D C10 H10B 83.7 . 12_655 ?
H10E C10 H10B 131.2 . 12_655 ?
H10F C10 H10B 28.2 . 12_655 ?
H10A C10 H10B 109.5 12_655 12_655 ?
N1 C10 H10C 109.5(10) . 12_655 ?
H10A C10 H10C 28.3 . 12_655 ?
H10B C10 H10C 131.2 . 12_655 ?
H10C C10 H10C 83.6 . 12_655 ?
H10D C10 H10C 131.2 . 12_655 ?
H10E C10 H10C 28.2 . 12_655 ?
H10F C10 H10C 83.7 . 12_655 ?
H10A C10 H10C 109.5 12_655 12_655 ?
H10B C10 H10C 109.5 12_655 12_655 ?
N1 C10 H10D 109.5(5) . 12_655 ?
H10A C10 H10D 28.2 . 12_655 ?
H10B C10 H10D 83.7 . 12_655 ?
H10C C10 H10D 131.2 . 12_655 ?
H10D C10 H10D 131.2 . 12_655 ?
H10E C10 H10D 83.6 . 12_655 ?
H10F C10 H10D 28.3 . 12_655 ?
H10A C10 H10D 141.1 12_655 12_655 ?
H10B C10 H10D 56.2 12_655 12_655 ?
H10C C10 H10D 56.3 12_655 12_655 ?
N1 C10 H10E 109.5(5) . 12_655 ?
H10A C10 H10E 83.7 . 12_655 ?
H10B C10 H10E 131.2 . 12_655 ?
H10C C10 H10E 28.2 . 12_655 ?
H10D C10 H10E 83.6 . 12_655 ?
H10E C10 H10E 28.3 . 12_655 ?
H10F C10 H10E 131.2 . 12_655 ?
H10A C10 H10E 56.3 12_655 12_655 ?
H10B C10 H10E 141.1 12_655 12_655 ?
H10C C10 H10E 56.2 12_655 12_655 ?
H10D C10 H10E 109.5 12_655 12_655 ?
N1 C10 H10F 109.5(10) . 12_655 ?
H10A C10 H10F 131.2 . 12_655 ?
H10B C10 H10F 28.2 . 12_655 ?
H10C C10 H10F 83.7 . 12_655 ?
H10D C10 H10F 28.3 . 12_655 ?
H10E C10 H10F 131.2 . 12_655 ?
H10F C10 H10F 83.6 . 12_655 ?
H10A C10 H10F 56.2 12_655 12_655 ?
H10B C10 H10F 56.3 12_655 12_655 ?
H10C C10 H10F 141.1 12_655 12_655 ?
H10D C10 H10F 109.5 12_655 12_655 ?
H10E C10 H10F 109.5 12_655 12_655 ?
C1 N1 N2 114.68(14) . . ?
C1 N1 C10 126.37(15) . . ?
N2 N1 C10 118.95(14) . . ?
N1 N2 C3 103.21(13) . . ?
O1 N3 O2 121.68(15) . . ?
O1 N3 C7 117.56(15) . . ?
O2 N3 C7 120.76(15) . . ?

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
N1 C1 C2 C7 180.000(1) . . . . ?
N1 C1 C2 C3 0.000(1) . . . . ?
C1 C2 C3 N2 0.000(1) . . . . ?
C7 C2 C3 N2 180.000(1) . . . . ?
C1 C2 C3 C4 180.000(1) . . . . ?
C7 C2 C3 C4 0.000(1) . . . . ?
N2 C3 C4 C5 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
C4 C5 C6 C8 180.000(1) . . . . ?
C5 C6 C7 C2 0.000(1) . . . . ?
C8 C6 C7 C2 180.000(1) . . . . ?
C5 C6 C7 N3 180.000(1) . . . . ?
C8 C6 C7 N3 0.000(1) . . . . ?
C1 C2 C7 C6 180.000(1) . . . . ?
C3 C2 C7 C6 0.000(1) . . . . ?
C1 C2 C7 N3 0.000(1) . . . . ?
C3 C2 C7 N3 180.000(1) . . . . ?
C7 C6 C8 C9 180.000(1) . . . . ?
C5 C6 C8 C9 0.000(1) . . . . ?
C2 C1 N1 N2 0.000(1) . . . . ?
C2 C1 N1 C10 180.000(1) . . . . ?
C1 N1 N2 C3 0.000(1) . . . . ?
C10 N1 N2 C3 180.000(1) . . . . ?
C4 C3 N2 N1 180.000(1) . . . . ?
C2 C3 N2 N1 0.000(1) . . . . ?
C6 C7 N3 O1 180.000(1) . . . . ?
C2 C7 N3 O1 0.000(1) . . . . ?
C6 C7 N3 O2 0.000(1) . . . . ?
C2 C7 N3 O2 180.000(1) . . . . ?

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
_geom_hbond_publ_flag
C4 H4 O1 0.95 2.45 3.104(2) 125.7 2_664 yes

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_4a1
_database_code_depnum_ccdc_archive 'CCDC 1914949'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro, CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

#=============================================================================
_audit_creation_method           'SHELXL-2018/3, manual editing plus enCIFer'
_audit_creation_date             '08 May 2019'
_shelx_SHELXL_version_number     2018/3
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N4 O2'
_chemical_formula_sum            'C10 H8 N4 O2'
_chemical_formula_weight         216.20

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_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                   9.2170(17)
_cell_length_b                   16.827(3)
_cell_length_c                   6.6121(13)
_cell_angle_alpha                90
_cell_angle_beta                 109.778(4)
_cell_angle_gamma                90
_cell_volume                     965.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6582
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.30

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   0.7104
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
  SADABS-2016/2
  Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  J. Appl. Cryst. 48 (2015) 3-10.
;

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16439
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.536
_diffrn_reflns_theta_max         25.336
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1755
_reflns_number_gt                1556
_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       'APEX2 2012.4 (Bruker, 2012b)'
_computing_cell_refinement       'SAINT V8.27b (Bruker, 2012a)'
_computing_data_reduction        'SAINT V8.27b (Bruker, 2012a)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.0416P)²+0.5833P] 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         1755
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 0.39180(17) 0.63547(9) 0.3254(2) 0.0236(3) Uani 1 1 d . . . . .
C2 C 0.38329(17) 0.59996(9) 0.5078(2) 0.0251(3) Uani 1 1 d . . . . .
H2 H 0.285699 0.588857 0.520545 0.030 Uiso 1 1 calc R U . . .
C3 C 0.51922(17) 0.58005(9) 0.6756(2) 0.0244(3) Uani 1 1 d . . . . .
H3 H 0.511236 0.554834 0.799972 0.029 Uiso 1 1 calc R U . . .
C4 C 0.66385(17) 0.59570(8) 0.6668(2) 0.0209(3) Uani 1 1 d . . . . .
C5 C 0.67051(16) 0.63321(8) 0.4783(2) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.53568(17) 0.65276(8) 0.3045(2) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.59085(18) 0.68994(9) 0.1532(2) 0.0264(4) Uani 1 1 d . . . . .
H7 H 0.526860 0.709449 0.017513 0.032 Uiso 1 1 calc R U . . .
C8 C 0.81030(18) 0.57632(10) 0.8504(2) 0.0278(4) Uani 1 1 d . . . . .
H8A H 0.880623 0.546855 0.792533 0.033 Uiso 1 1 calc R U . . .
H8B H 0.861928 0.626671 0.912369 0.033 Uiso 1 1 calc R U . . .
C9 C 0.78595(18) 0.52912(10) 1.0225(2) 0.0275(4) Uani 1 1 d . . . . .
C10 C 0.95672(18) 0.65957(11) 0.5428(3) 0.0329(4) Uani 1 1 d . . . . .
H10A H 1.012061 0.684666 0.456536 0.049 Uiso 0.5 1 calc R U P . .
H10B H 0.992749 0.604745 0.576161 0.049 Uiso 0.5 1 calc R U P . .
H10C H 0.976189 0.689355 0.676728 0.049 Uiso 0.5 1 calc R U P . .
H10D H 0.975272 0.634512 0.683081 0.049 Uiso 0.5 1 calc R U P . .
H10E H 0.994584 0.714432 0.563456 0.049 Uiso 0.5 1 calc R U P . .
H10F H 1.011144 0.629823 0.462888 0.049 Uiso 0.5 1 calc R U P . .
N1 N 0.24969(15) 0.65874(8) 0.1554(2) 0.0294(3) Uani 1 1 d . . . . .
N2 N 0.74316(15) 0.69409(8) 0.2249(2) 0.0285(3) Uani 1 1 d . . . . .
N3 N 0.79190(14) 0.65948(7) 0.42213(19) 0.0229(3) Uani 1 1 d . . . . .
N4 N 0.77199(18) 0.49187(9) 1.1591(2) 0.0371(4) Uani 1 1 d . . . . .
O1 O 0.25993(14) 0.70020(8) 0.0086(2) 0.0439(4) Uani 1 1 d . . . . .
O2 O 0.12617(13) 0.63574(8) 0.1676(2) 0.0398(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
C1 C2 1.372(2) . ?
C1 C6 1.409(2) . ?
C1 N1 1.4616(19) . ?
C2 C3 1.404(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(2) . ?
C4 C8 1.514(2) . ?
C5 N3 1.3661(19) . ?
C5 C6 1.416(2) . ?
C6 C7 1.412(2) . ?
C7 N2 1.323(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.466(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N4 1.142(2) . ?
C10 N3 1.457(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
N1 O1 1.2245(18) . ?
N1 O2 1.2307(18) . ?
N2 N3 1.3581(18) . ?

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 C6 120.78(14) . . ?
C2 C1 N1 119.34(14) . . ?
C6 C1 N1 119.82(14) . . ?
C1 C2 C3 119.83(14) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 122.53(14) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 116.89(13) . . ?
C3 C4 C8 122.51(13) . . ?
C5 C4 C8 120.58(13) . . ?
N3 C5 C6 106.19(12) . . ?
N3 C5 C4 131.80(13) . . ?
C6 C5 C4 121.99(13) . . ?
C1 C6 C7 137.48(14) . . ?
C1 C6 C5 117.96(13) . . ?
C7 C6 C5 104.49(13) . . ?
N2 C7 C6 111.23(13) . . ?
N2 C7 H7 124.4 . . ?
C6 C7 H7 124.4 . . ?
C9 C8 C4 114.19(13) . . ?
C9 C8 H8A 108.7 . . ?
C4 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C4 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N4 C9 C8 177.78(17) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
N3 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
N3 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
O1 N1 O2 123.51(13) . . ?
O1 N1 C1 118.22(13) . . ?
O2 N1 C1 118.26(14) . . ?
C7 N2 N3 106.72(12) . . ?
N2 N3 C5 111.37(12) . . ?
N2 N3 C10 118.03(12) . . ?
C5 N3 C10 130.50(13) . . ?

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 C1 C2 C3 -0.4(2) . . . . ?
N1 C1 C2 C3 -177.62(13) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C8 178.24(14) . . . . ?
C3 C4 C5 N3 176.95(14) . . . . ?
C8 C4 C5 N3 -1.5(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C8 C4 C5 C6 -179.45(13) . . . . ?
C2 C1 C6 C7 -177.02(16) . . . . ?
N1 C1 C6 C7 0.2(3) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
N1 C1 C6 C5 176.49(12) . . . . ?
N3 C5 C6 C1 -176.96(12) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
N3 C5 C6 C7 0.44(15) . . . . ?
C4 C5 C6 C7 178.88(13) . . . . ?
C1 C6 C7 N2 175.97(17) . . . . ?
C5 C6 C7 N2 -0.63(17) . . . . ?
C3 C4 C8 C9 8.8(2) . . . . ?
C5 C4 C8 C9 -172.93(13) . . . . ?
C2 C1 N1 O1 169.78(14) . . . . ?
C6 C1 N1 O1 -7.5(2) . . . . ?
C2 C1 N1 O2 -10.1(2) . . . . ?
C6 C1 N1 O2 172.64(13) . . . . ?
C6 C7 N2 N3 0.57(17) . . . . ?
C7 N2 N3 C5 -0.27(17) . . . . ?
C7 N2 N3 C10 -177.04(14) . . . . ?
C6 C5 N3 N2 -0.12(16) . . . . ?
C4 C5 N3 N2 -178.35(15) . . . . ?
C6 C5 N3 C10 176.12(15) . . . . ?
C4 C5 N3 C10 -2.1(3) . . . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1914952'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro, CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

#=============================================================================
_audit_creation_method           'SHELXL-2018/3, manual editing plus enCIFer'
_audit_creation_date             '08 May 2019'
_shelx_SHELXL_version_number     2018/3
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N4 O2'
_chemical_formula_sum            'C10 H8 N4 O2'
_chemical_formula_weight         216.20

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_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                   9.5041(12)
_cell_length_b                   10.9669(14)
_cell_length_c                   9.1780(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.857(3)
_cell_angle_gamma                90
_cell_volume                     953.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8174
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      25.36

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   0.6956
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
  SADABS-2016/2
  Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  J. Appl. Cryst. 48 (2015) 3-10.
;

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14743
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.716
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1743
_reflns_number_gt                1598
_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       'APEX2 2012.4 (Bruker, 2012b)'
_computing_cell_refinement       'SAINT V8.27b (Bruker, 2012a)'
_computing_data_reduction        'SAINT V8.27b (Bruker, 2012a)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.0443P)²+0.3847P] 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         1743
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 0.51561(11) 0.38172(10) 0.72229(11) 0.0382(3) Uani 1 1 d . . . . .
O2 O 0.58241(11) 0.55602(9) 0.64375(11) 0.0344(3) Uani 1 1 d . . . . .
N1 N 0.33593(12) 0.17253(12) 0.51433(13) 0.0368(3) Uani 1 1 d . . . . .
N2 N 0.58761(11) 0.44400(10) 0.64585(11) 0.0245(3) Uani 1 1 d . . . . .
N3 N 0.97701(10) 0.22188(9) 0.31684(11) 0.0218(2) Uani 1 1 d . . . . .
N4 N 0.95359(11) 0.10059(10) 0.33949(12) 0.0250(3) Uani 1 1 d . . . . .
C1 C 0.45205(13) 0.17096(12) 0.55914(13) 0.0250(3) Uani 1 1 d . . . . .
C2 C 0.60128(12) 0.16507(12) 0.61649(14) 0.0237(3) Uani 1 1 d . . . . .
H2A H 0.637599 0.081927 0.600698 0.028 Uiso 1 1 calc R U . . .
H2B H 0.607952 0.180216 0.723186 0.028 Uiso 1 1 calc R U . . .
C3 C 0.69369(12) 0.25696(11) 0.54481(12) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.68607(12) 0.38352(12) 0.55394(13) 0.0209(3) Uani 1 1 d . . . . .
C5 C 0.77155(13) 0.46327(11) 0.47764(13) 0.0232(3) Uani 1 1 d . . . . .
H5 H 0.758883 0.548854 0.485779 0.028 Uiso 1 1 calc R U . . .
C6 C 0.87207(12) 0.41961(12) 0.39239(13) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.928924 0.472628 0.340288 0.026 Uiso 1 1 calc R U . . .
C7 C 0.88643(12) 0.29236(12) 0.38626(12) 0.0192(3) Uani 1 1 d . . . . .
C8 C 0.79877(12) 0.21224(11) 0.45863(12) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.84748(13) 0.09386(11) 0.42294(14) 0.0229(3) Uani 1 1 d . . . . .
H9 H 0.808574 0.019764 0.455076 0.027 Uiso 1 1 calc R U . . .
C10 C 1.09206(13) 0.26089(13) 0.23170(14) 0.0262(3) Uani 1 1 d . . . . .
H10A H 1.148309 0.189836 0.207937 0.039 Uiso 0.5 1 calc R U P . .
H10B H 1.152210 0.319161 0.288947 0.039 Uiso 0.5 1 calc R U P . .
H10C H 1.052829 0.299849 0.141107 0.039 Uiso 0.5 1 calc R U P . .
H10D H 1.087256 0.349394 0.217391 0.039 Uiso 0.5 1 calc R U P . .
H10E H 1.083355 0.220069 0.136381 0.039 Uiso 0.5 1 calc R U P . .
H10F H 1.182736 0.239382 0.284221 0.039 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
O1 N2 1.2281(14) . ?
O2 N2 1.2296(15) . ?
N1 C1 1.1448(17) . ?
N2 C4 1.4700(15) . ?
N3 C7 1.3556(15) . ?
N3 N4 1.3674(15) . ?
N3 C10 1.4607(15) . ?
N4 C9 1.3191(17) . ?
C1 C2 1.4718(17) . ?
C2 C3 1.5223(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.3927(18) . ?
C3 C8 1.4133(16) . ?
C4 C5 1.4183(17) . ?
C5 C6 1.3714(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4037(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4146(16) . ?
C8 C9 1.4257(17) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 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
O1 N2 O2 122.75(11) . . ?
O1 N2 C4 119.30(11) . . ?
O2 N2 C4 117.94(10) . . ?
C7 N3 N4 111.42(10) . . ?
C7 N3 C10 128.19(11) . . ?
N4 N3 C10 120.34(10) . . ?
C9 N4 N3 106.56(10) . . ?
N1 C1 C2 178.35(14) . . ?
C1 C2 C3 112.97(10) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C8 114.98(10) . . ?
C4 C3 C2 126.79(11) . . ?
C8 C3 C2 118.23(11) . . ?
C3 C4 C5 123.37(11) . . ?
C3 C4 N2 121.54(11) . . ?
C5 C4 N2 115.09(11) . . ?
C6 C5 C4 121.48(11) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 116.41(11) . . ?
C5 C6 H6 121.8 . . ?
C7 C6 H6 121.8 . . ?
N3 C7 C6 130.81(11) . . ?
N3 C7 C8 106.81(11) . . ?
C6 C7 C8 122.38(11) . . ?
C3 C8 C7 121.29(11) . . ?
C3 C8 C9 134.69(11) . . ?
C7 C8 C9 104.01(10) . . ?
N4 C9 C8 111.19(11) . . ?
N4 C9 H9 124.4 . . ?
C8 C9 H9 124.4 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
N3 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
N3 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 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
C7 N3 N4 C9 0.28(13) . . . . ?
C10 N3 N4 C9 177.94(10) . . . . ?
C1 C2 C3 C4 65.20(16) . . . . ?
C1 C2 C3 C8 -114.45(12) . . . . ?
C8 C3 C4 C5 2.98(17) . . . . ?
C2 C3 C4 C5 -176.67(11) . . . . ?
C8 C3 C4 N2 -176.60(9) . . . . ?
C2 C3 C4 N2 3.74(18) . . . . ?
O1 N2 C4 C3 3.86(16) . . . . ?
O2 N2 C4 C3 -176.98(11) . . . . ?
O1 N2 C4 C5 -175.76(11) . . . . ?
O2 N2 C4 C5 3.41(15) . . . . ?
C3 C4 C5 C6 -2.22(18) . . . . ?
N2 C4 C5 C6 177.39(10) . . . . ?
C4 C5 C6 C7 -0.65(17) . . . . ?
N4 N3 C7 C6 -179.63(12) . . . . ?
C10 N3 C7 C6 2.9(2) . . . . ?
N4 N3 C7 C8 0.06(12) . . . . ?
C10 N3 C7 C8 -177.38(11) . . . . ?
C5 C6 C7 N3 -177.81(11) . . . . ?
C5 C6 C7 C8 2.54(17) . . . . ?
C4 C3 C8 C7 -1.05(15) . . . . ?
C2 C3 C8 C7 178.63(10) . . . . ?
C4 C3 C8 C9 177.44(12) . . . . ?
C2 C3 C8 C9 -2.87(19) . . . . ?
N3 C7 C8 C3 178.56(10) . . . . ?
C6 C7 C8 C3 -1.72(17) . . . . ?
N3 C7 C8 C9 -0.34(12) . . . . ?
C6 C7 C8 C9 179.38(11) . . . . ?
N3 N4 C9 C8 -0.51(13) . . . . ?
C3 C8 C9 N4 -178.14(12) . . . . ?
C7 C8 C9 N4 0.53(13) . . . . ?

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
_geom_hbond_publ_flag
C2 H2B O2 0.99 2.64 3.1577(15) 112.4 2_646 yes
C6 H6 N4 0.95 2.50 3.4368(16) 168.7 2_755 yes
C9 H9 N1 0.95 2.55 3.4749(18) 166.1 3_656 yes
C10 H10F N1 0.98 2.57 3.4673(18) 152.5 1_655 yes

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_4c
_database_code_depnum_ccdc_archive 'CCDC 1914951'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro, CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;


#=============================================================================
_audit_creation_method           'SHELXL-2018/3, manual editing plus enCIFer'
_audit_creation_date             '08 May 2019'
_shelx_SHELXL_version_number     2018/3
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N4 O2'
_chemical_formula_sum            'C10 H8 N4 O2'
_chemical_formula_weight         216.20

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_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                   7.6034(4)
_cell_length_b                   14.7108(7)
_cell_length_c                   8.7184(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.023(2)
_cell_angle_gamma                90
_cell_volume                     960.29(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6376
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      25.32

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   0.7225
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
  SADABS-2016/2
  Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  J. Appl. Cryst. 48 (2015) 3-10.
;

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14420
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.565
_diffrn_reflns_theta_max         25.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1757
_reflns_number_gt                1598
_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       'APEX2 2012.4 (Bruker, 2012b)'
_computing_cell_refinement       'SAINT V8.27b (Bruker, 2012a)'
_computing_data_reduction        'SAINT V8.27b (Bruker, 2012a)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.0484P)²+0.6087P] 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         1757
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 0.60844(18) 0.21591(9) 0.68887(15) 0.0403(4) Uani 1 1 d . . . . .
O2 O 0.48208(17) 0.22128(9) 0.44659(15) 0.0360(3) Uani 1 1 d . . . . .
N1 N 0.4484(2) 0.33163(11) 0.04266(17) 0.0359(4) Uani 1 1 d . . . . .
N2 N 0.57520(18) 0.25488(10) 0.56191(16) 0.0278(3) Uani 1 1 d . . . . .
N3 N 0.84226(19) 0.60584(9) 0.35263(17) 0.0279(3) Uani 1 1 d . . . . .
N4 N 0.80775(18) 0.51912(9) 0.30139(15) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.5608(2) 0.32203(11) 0.14743(19) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.7098(2) 0.31150(11) 0.27777(18) 0.0222(4) Uani 1 1 d . . . . .
H2A H 0.823150 0.323275 0.240005 0.027 Uiso 1 1 calc R U . . .
H2B H 0.712581 0.247862 0.315045 0.027 Uiso 1 1 calc R U . . .
C3 C 0.6982(2) 0.37469(10) 0.41347(18) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.6461(2) 0.34688(11) 0.55066(18) 0.0231(4) Uani 1 1 d . . . . .
C5 C 0.6497(2) 0.40157(12) 0.68437(19) 0.0278(4) Uani 1 1 d . . . . .
H5 H 0.616122 0.376925 0.775771 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7022(2) 0.49053(12) 0.68081(18) 0.0277(4) Uani 1 1 d . . . . .
H6 H 0.703753 0.528817 0.768790 0.033 Uiso 1 1 calc R U . . .
C7 C 0.7535(2) 0.52385(11) 0.54448(18) 0.0238(4) Uani 1 1 d . . . . .
C8 C 0.7523(2) 0.46641(11) 0.41348(17) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.8111(2) 0.60879(11) 0.4965(2) 0.0278(4) Uani 1 1 d . . . . .
H9 H 0.825586 0.661602 0.560210 0.033 Uiso 1 1 calc R U . . .
C10 C 0.8322(2) 0.49840(11) 0.14335(19) 0.0294(4) Uani 1 1 d . . . . .
H10A H 0.873902 0.552879 0.095822 0.044 Uiso 0.5 1 calc R U P . .
H10B H 0.718290 0.478529 0.081976 0.044 Uiso 0.5 1 calc R U P . .
H10C H 0.920833 0.449825 0.145757 0.044 Uiso 0.5 1 calc R U P . .
H10D H 0.801448 0.434610 0.119882 0.044 Uiso 0.5 1 calc R U P . .
H10E H 0.957060 0.508960 0.133727 0.044 Uiso 0.5 1 calc R U P . .
H10F H 0.754517 0.537664 0.069946 0.044 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
O1 N2 1.2331(18) . ?
O2 N2 1.2282(19) . ?
N1 C1 1.146(2) . ?
N2 C4 1.466(2) . ?
N3 C9 1.318(2) . ?
N3 N4 1.3620(19) . ?
N4 C8 1.370(2) . ?
N4 C10 1.454(2) . ?
C1 C2 1.467(2) . ?
C2 C3 1.519(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.386(2) . ?
C3 C8 1.411(2) . ?
C4 C5 1.413(2) . ?
C5 C6 1.370(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(2) . ?
C6 H6 0.9500 . ?
C7 C9 1.411(2) . ?
C7 C8 1.419(2) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 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
O2 N2 O1 123.13(15) . . ?
O2 N2 C4 118.87(13) . . ?
O1 N2 C4 117.96(14) . . ?
C9 N3 N4 106.67(14) . . ?
N3 N4 C8 111.21(13) . . ?
N3 N4 C10 117.25(13) . . ?
C8 N4 C10 131.53(13) . . ?
N1 C1 C2 177.62(18) . . ?
C1 C2 C3 113.40(13) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C8 114.18(14) . . ?
C4 C3 C2 123.75(14) . . ?
C8 C3 C2 121.93(14) . . ?
C3 C4 C5 125.22(15) . . ?
C3 C4 N2 119.60(14) . . ?
C5 C4 N2 115.16(14) . . ?
C6 C5 C4 119.29(15) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 118.56(15) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C9 134.98(16) . . ?
C6 C7 C8 120.67(15) . . ?
C9 C7 C8 104.34(14) . . ?
N4 C8 C3 131.86(14) . . ?
N4 C8 C7 106.10(14) . . ?
C3 C8 C7 122.04(14) . . ?
N3 C9 C7 111.67(15) . . ?
N3 C9 H9 124.2 . . ?
C7 C9 H9 124.2 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
N4 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
N4 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 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
C9 N3 N4 C8 0.57(18) . . . . ?
C9 N3 N4 C10 179.85(14) . . . . ?
C1 C2 C3 C4 103.71(17) . . . . ?
C1 C2 C3 C8 -80.77(18) . . . . ?
C8 C3 C4 C5 -2.1(2) . . . . ?
C2 C3 C4 C5 173.75(15) . . . . ?
C8 C3 C4 N2 175.84(13) . . . . ?
C2 C3 C4 N2 -8.3(2) . . . . ?
O2 N2 C4 C3 -36.1(2) . . . . ?
O1 N2 C4 C3 145.88(15) . . . . ?
O2 N2 C4 C5 142.05(15) . . . . ?
O1 N2 C4 C5 -36.0(2) . . . . ?
C3 C4 C5 C6 2.5(2) . . . . ?
N2 C4 C5 C6 -175.54(14) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C9 178.83(17) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
N3 N4 C8 C3 178.28(15) . . . . ?
C10 N4 C8 C3 -0.9(3) . . . . ?
N3 N4 C8 C7 -0.48(17) . . . . ?
C10 N4 C8 C7 -179.62(16) . . . . ?
C4 C3 C8 N4 -178.15(15) . . . . ?
C2 C3 C8 N4 5.9(3) . . . . ?
C4 C3 C8 C7 0.4(2) . . . . ?
C2 C3 C8 C7 -175.47(13) . . . . ?
C6 C7 C8 N4 179.68(14) . . . . ?
C9 C7 C8 N4 0.20(16) . . . . ?
C6 C7 C8 C3 0.8(2) . . . . ?
C9 C7 C8 C3 -178.71(14) . . . . ?
N4 N3 C9 C7 -0.44(19) . . . . ?
C6 C7 C9 N3 -179.22(17) . . . . ?
C8 C7 C9 N3 0.15(18) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.043

