# 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 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1982198'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-05-27 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         ?
_chemical_formula_sum            'C14 H12 N4 O2 S1'
_chemical_formula_weight         300.34

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'

_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                   9.187(3)
_cell_length_b                   34.222(10)
_cell_length_c                   4.7335(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.932(8)
_cell_angle_gamma                90
_cell_volume                     1415.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.936
_cell_measurement_theta_max      26.510

_exptl_crystal_description       block
_exptl_crystal_colour            ?


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.238
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.991

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.991

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9969
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.936
_diffrn_reflns_theta_max         26.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2864
_reflns_number_gt                1432
_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       'BRUKER SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 4.1.0'
_computing_publication_material  ?
_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)+(0.0622P)²+0.3088P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2864
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.8747(4) 0.30081(10) 0.0385(7) 0.0583(9) Uani 1 1 d . . . . .
C2 C 0.7427(4) 0.28926(11) 0.0928(8) 0.0664(10) Uani 1 1 d . . . . .
H2 H 0.7021 0.2645 0.0375 0.080 Uiso 1 1 calc R U . . .
C3 C 0.6723(4) 0.31475(10) 0.2293(8) 0.0646(10) Uani 1 1 d . . . . .
H3 H 0.5834 0.3070 0.2685 0.078 Uiso 1 1 calc R U . . .
C4 C 0.7301(3) 0.35207(9) 0.3117(6) 0.0512(8) Uani 1 1 d . . . . .
C5 C 0.8646(4) 0.36251(10) 0.2544(7) 0.0588(9) Uani 1 1 d . . . . .
H5 H 0.9068 0.3871 0.3110 0.071 Uiso 1 1 calc R U . . .
C6 C 0.9360(4) 0.33701(10) 0.1153(8) 0.0642(10) Uani 1 1 d . . . . .
H6 H 1.0249 0.3444 0.0743 0.077 Uiso 1 1 calc R U . . .
C7 C 0.6487(3) 0.37945(9) 0.4518(7) 0.0508(8) Uani 1 1 d . . . . .
C8 C 0.6936(4) 0.42133(10) 0.4926(7) 0.0563(8) Uani 1 1 d D . . . .
C14 C 0.3361(4) 0.37292(11) 0.7309(7) 0.0567(9) Uani 1 1 d . . . . .
N1 N 0.9483(4) 0.27361(10) -0.1116(8) 0.0767(10) Uani 1 1 d . . . . .
N2 N 0.5375(3) 0.36420(7) 0.5274(6) 0.0550(7) Uani 1 1 d . . . . .
N3 N 0.4559(3) 0.38756(8) 0.6547(6) 0.0575(7) Uani 1 1 d . . . . .
N4 N 0.3118(4) 0.33518(10) 0.6870(8) 0.0777(11) Uani 1 1 d . . . . .
O1 O 1.0560(3) 0.28460(8) -0.1872(7) 0.1047(11) Uani 1 1 d . . . . .
O2 O 0.8957(4) 0.24074(10) -0.1617(8) 0.1141(12) Uani 1 1 d . . . . .
S1 S 0.23157(11) 0.40195(3) 0.8721(2) 0.0773(4) Uani 1 1 d . . . . .
C11 C 0.7814(5) 0.50014(14) 0.5669(14) 0.0974(15) Uani 1 1 d . . . . .
H11 H 0.8225 0.5252 0.5919 0.117 Uiso 1 1 calc R U . A 1
C13 C 0.8370(6) 0.42844(13) 0.6669(11) 0.0584(12) Uani 0.7 1 d . . P B 2
H13 H 0.9040 0.4085 0.7563 0.070 Uiso 0.7 1 calc R U P B 2
C9 C 0.5935(7) 0.44721(13) 0.3486(14) 0.0758(17) Uani 0.7 1 d . . P B 2
H9 H 0.4972 0.4398 0.2271 0.091 Uiso 0.7 1 calc R U P B 2
C12 C 0.8781(6) 0.46721(14) 0.7041(15) 0.0808(17) Uani 0.7 1 d . . P B 2
H12 H 0.9760 0.4729 0.8276 0.097 Uiso 0.7 1 calc R U P B 2
C10 C 0.6362(8) 0.48594(15) 0.3837(19) 0.111(3) Uani 0.7 1 d . . P B 2
H10 H 0.5652 0.5043 0.2803 0.133 Uiso 0.7 1 calc R U P B 2
C12A C 0.7864(12) 0.4860(3) 0.807(2) 0.043(2) Uani 0.3 1 d . . P B 1
H12A H 0.8148 0.4998 0.9849 0.051 Uiso 0.3 1 calc R U P B 1
C13A C 0.7441(11) 0.4465(3) 0.780(2) 0.042(2) Uani 0.3 1 d D . P B 1
H13A H 0.7466 0.4338 0.9550 0.051 Uiso 0.3 1 calc R U P B 1
C10A C 0.7389(14) 0.4913(3) 0.304(3) 0.048(3) Uani 0.3 1 d . . P B 1
H10A H 0.7357 0.5086 0.1505 0.058 Uiso 0.3 1 calc R U P B 1
C9A C 0.6960(12) 0.4524(3) 0.262(2) 0.045(2) Uani 0.3 1 d . . P B 1
H9A H 0.6641 0.4440 0.0657 0.053 Uiso 0.3 1 calc R U P B 1
H1N H 0.360(4) 0.3239(9) 0.592(7) 0.053 Uiso 1 1 d . U . . .
H2N H 0.247(4) 0.3248(9) 0.742(7) 0.053 Uiso 1 1 d . U . . .
H3N H 0.464(3) 0.4129(8) 0.670(7) 0.053 Uiso 1 1 d . 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 C6 1.363(4) . ?
C1 C2 1.373(4) . ?
C1 N1 1.457(4) . ?
C2 C3 1.361(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 C7 1.477(4) . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.292(3) . ?
C7 C8 1.487(4) . ?
C8 C9 1.307(6) . ?
C8 C13 1.344(5) . ?
C8 C9A 1.529(9) . ?
C8 C13A 1.555(9) . ?
C14 N4 1.316(5) . ?
C14 N3 1.356(4) . ?
C14 S1 1.658(3) . ?
N1 O1 1.211(3) . ?
N1 O2 1.218(4) . ?
N2 N3 1.357(3) . ?
N3 H3N 0.87(3) . ?
N4 H1N 0.82(3) . ?
N4 H2N 0.80(3) . ?
C11 C12A 1.222(11) . ?
C11 C10A 1.222(12) . ?
C11 C10 1.434(7) . ?
C11 C12 1.458(7) . ?
C11 H11 0.9300 . ?
C13 C12 1.376(6) . ?
C13 H13 0.9300 . ?
C9 C10 1.378(7) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C12A C13A 1.404(12) . ?
C12A H12A 0.9300 . ?
C13A H13A 0.9300 . ?
C10A C9A 1.386(14) . ?
C10A H10A 0.9300 . ?
C9A H9A 0.9300 . ?

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
C6 C1 C2 121.9(3) . . ?
C6 C1 N1 119.7(3) . . ?
C2 C1 N1 118.4(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 C7 121.8(3) . . ?
C3 C4 C7 120.4(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N2 C7 C4 114.9(3) . . ?
N2 C7 C8 124.4(3) . . ?
C4 C7 C8 120.7(2) . . ?
C9 C8 C13 126.6(4) . . ?
C9 C8 C7 117.6(3) . . ?
C13 C8 C7 115.7(3) . . ?
C7 C8 C9A 129.9(5) . . ?
C7 C8 C13A 130.0(4) . . ?
C9A C8 C13A 100.0(5) . . ?
N4 C14 N3 115.6(3) . . ?
N4 C14 S1 124.1(2) . . ?
N3 C14 S1 120.3(3) . . ?
O1 N1 O2 122.7(3) . . ?
O1 N1 C1 119.3(3) . . ?
O2 N1 C1 118.0(3) . . ?
C7 N2 N3 118.5(3) . . ?
C14 N3 N2 120.4(3) . . ?
C14 N3 H3N 114(2) . . ?
N2 N3 H3N 125(2) . . ?
C14 N4 H1N 117(2) . . ?
C14 N4 H2N 119(2) . . ?
H1N N4 H2N 123(3) . . ?
C12A C11 C10A 139.3(8) . . ?
C10 C11 C12 109.5(4) . . ?
C12A C11 H11 110.4 . . ?
C10A C11 H11 110.4 . . ?
C8 C13 C12 115.6(4) . . ?
C8 C13 H13 122.2 . . ?
C12 C13 H13 122.2 . . ?
C8 C9 C10 117.4(5) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C13 C12 C11 125.7(5) . . ?
C13 C12 H12 117.2 . . ?
C11 C12 H12 117.2 . . ?
C9 C10 C11 125.2(5) . . ?
C9 C10 H10 117.4 . . ?
C11 C10 H10 117.4 . . ?
C11 C12A C13A 111.5(8) . . ?
C11 C12A H12A 124.3 . . ?
C13A C12A H12A 124.3 . . ?
C12A C13A C8 127.8(8) . . ?
C12A C13A H13A 116.1 . . ?
C8 C13A H13A 116.1 . . ?
C11 C10A C9A 111.8(9) . . ?
C11 C10A H10A 124.1 . . ?
C9A C10A H10A 124.1 . . ?
C10A C9A C8 129.2(9) . . ?
C10A C9A H9A 115.4 . . ?
C8 C9A H9A 115.4 . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.044

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1982199'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-05-27 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         ?
_chemical_formula_sum            'C14 H14 Ag1 N5 O7'
_chemical_formula_weight         472.17

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'
Ag Ag -0.8971 1.1015 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.968(3)
_cell_length_b                   9.327(4)
_cell_length_c                   11.613(4)
_cell_angle_alpha                95.389(16)
_cell_angle_beta                 95.673(16)
_cell_angle_gamma                104.311(16)
_cell_volume                     929.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3818
_cell_measurement_theta_min      2.771
_cell_measurement_theta_max      26.664

_exptl_crystal_description       plate
_exptl_crystal_colour            ?


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.131
_shelx_estimated_absorpt_T_min   0.805
_shelx_estimated_absorpt_T_max   0.935

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_T_max  0.935

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10962
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.771
_diffrn_reflns_theta_max         26.664
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3818
_reflns_number_gt                3346
_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       'BRUKER SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 4.1.0'
_computing_publication_material  ?
_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)+(0.0508P)²+0.5735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3818
_refine_ls_number_parameters     260
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.14978(3) 0.47062(3) 0.42640(2) 0.03844(12) Uani 1 1 d . U . . .
O3 O -0.0868(3) 0.2855(3) 0.2318(2) 0.0488(7) Uani 1 1 d . . . . .
O1W O 0.0296(5) 0.0857(4) 0.3373(3) 0.0638(9) Uani 1 1 d D . . . .
N3 N 0.1343(4) 0.4669(3) 0.2429(2) 0.0352(6) Uani 1 1 d D . . . .
O2 O 0.7123(4) 0.8739(4) -0.1985(3) 0.0737(11) Uani 1 1 d . . . . .
N2 N 0.2323(4) 0.5424(3) 0.1738(2) 0.0372(7) Uani 1 1 d . . . . .
O4 O 0.1635(4) 0.4519(4) 0.6055(3) 0.0566(8) Uani 1 1 d . U . . .
N1 N 0.7307(4) 0.9347(4) -0.0994(3) 0.0505(9) Uani 1 1 d . . . . .
O5 O 0.1101(4) 0.1956(4) 0.5916(3) 0.0674(9) Uani 1 1 d . . . . .
C4 C 0.4460(4) 0.7294(4) 0.1382(3) 0.0358(8) Uani 1 1 d . . . . .
O1 O 0.8261(5) 1.0515(4) -0.0682(3) 0.0916(14) Uani 1 1 d . . . . .
C5 C 0.5563(4) 0.8632(4) 0.1723(3) 0.0392(8) Uani 1 1 d . . . . .
H5 H 0.5676 0.9070 0.2491 0.047 Uiso 1 1 calc R U . . .
C7 C 0.3443(4) 0.6559(4) 0.2196(3) 0.0343(7) Uani 1 1 d . . . . .
C8 C 0.3739(4) 0.7139(4) 0.3458(3) 0.0334(7) Uani 1 1 d . . . . .
C6 C 0.6497(4) 0.9335(4) 0.0966(3) 0.0420(9) Uani 1 1 d . . . . .
H6 H 0.7220 1.0243 0.1210 0.050 Uiso 1 1 calc R U . . .
C1 C 0.6337(4) 0.8659(4) -0.0166(3) 0.0394(8) Uani 1 1 d . . . . .
N4 N 0.0003(6) 0.3470(5) 0.0643(3) 0.0704(13) Uani 1 1 d D . . . .
C14 C 0.0136(5) 0.3612(4) 0.1800(3) 0.0408(8) Uani 1 1 d . . . . .
N5 N 0.1381(4) 0.3310(4) 0.6548(3) 0.0516(9) Uani 1 1 d . . . . .
C9 C 0.4859(4) 0.6754(4) 0.4188(3) 0.0418(9) Uani 1 1 d . . . . .
H9 H 0.5463 0.6169 0.3882 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2888(5) 0.8041(4) 0.3936(3) 0.0445(9) Uani 1 1 d . . . . .
H13 H 0.2146 0.8323 0.3455 0.053 Uiso 1 1 calc R U . . .
C3 C 0.4331(5) 0.6660(5) 0.0223(4) 0.0553(11) Uani 1 1 d . . . . .
H3 H 0.3595 0.5763 -0.0031 0.066 Uiso 1 1 calc R U . . .
C2 C 0.5260(5) 0.7326(5) -0.0542(4) 0.0559(12) Uani 1 1 d . . . . .
H2 H 0.5166 0.6884 -0.1307 0.067 Uiso 1 1 calc R U . . .
C12 C 0.3124(6) 0.8527(5) 0.5109(4) 0.0561(11) Uani 1 1 d . . . . .
H12 H 0.2542 0.9134 0.5415 0.067 Uiso 1 1 calc R U . . .
C10 C 0.5080(5) 0.7237(5) 0.5365(4) 0.0532(11) Uani 1 1 d . . . . .
H10 H 0.5823 0.6965 0.5852 0.064 Uiso 1 1 calc R U . . .
C11 C 0.4206(6) 0.8122(5) 0.5826(4) 0.0558(11) Uani 1 1 d . . . . .
H11 H 0.4354 0.8441 0.6622 0.067 Uiso 1 1 calc R U . . .
O6 O 0.1385(6) 0.3339(6) 0.7853(3) 0.1058(15) Uani 1 1 d . . . . .
H3N H 0.0740 0.5413 0.2440 0.127 Uiso 1 1 d D U . . .
H1W H 0.113(5) 0.076(8) 0.307(5) 0.12(3) Uiso 1 1 d D . . . .
H2N H -0.065(5) 0.264(3) 0.031(4) 0.066(14) Uiso 1 1 d D . . . .
H1N H 0.086(4) 0.373(7) 0.031(5) 0.10(2) Uiso 1 1 d D . . . .
H2W H -0.011(8) 0.161(6) 0.320(6) 0.12(3) Uiso 1 1 d 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
Ag1 O4 2.098(3) . ?
Ag1 N3 2.118(3) . ?
O3 C14 1.243(4) . ?
O1W H1W 0.88(2) . ?
O1W H2W 0.89(2) . ?
N3 N2 1.362(4) . ?
N3 C14 1.363(5) . ?
N3 H3N 0.979(3) . ?
O2 N1 1.212(5) . ?
N2 C7 1.294(5) . ?
O4 N5 1.292(5) . ?
N1 O1 1.205(5) . ?
N1 C1 1.449(5) . ?
O5 N5 1.353(5) . ?
C4 C5 1.382(5) . ?
C4 C3 1.400(5) . ?
C4 C7 1.476(5) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.488(5) . ?
C8 C13 1.383(5) . ?
C8 C9 1.386(5) . ?
C6 C1 1.381(5) . ?
C6 H6 0.9300 . ?
C1 C2 1.375(5) . ?
N4 C14 1.328(5) . ?
N4 H2N 0.876(19) . ?
N4 H1N 0.88(2) . ?
N5 O6 1.513(5) . ?
C9 C10 1.378(6) . ?
C9 H9 0.9300 . ?
C13 C12 1.373(6) . ?
C13 H13 0.9300 . ?
C3 C2 1.366(6) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C12 C11 1.364(7) . ?
C12 H12 0.9300 . ?
C10 C11 1.380(7) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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
O4 Ag1 N3 174.41(11) . . ?
H1W O1W H2W 119(6) . . ?
N2 N3 C14 112.3(3) . . ?
N2 N3 Ag1 131.5(2) . . ?
C14 N3 Ag1 115.9(2) . . ?
N2 N3 H3N 92.0(3) . . ?
C14 N3 H3N 91.8(3) . . ?
Ag1 N3 H3N 91.94(19) . . ?
C7 N2 N3 119.7(3) . . ?
N5 O4 Ag1 127.6(3) . . ?
O1 N1 O2 121.9(4) . . ?
O1 N1 C1 119.2(4) . . ?
O2 N1 C1 118.9(3) . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 C7 121.8(3) . . ?
C3 C4 C7 120.8(3) . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
N2 C7 C4 115.9(3) . . ?
N2 C7 C8 124.2(3) . . ?
C4 C7 C8 119.8(3) . . ?
C13 C8 C9 118.5(3) . . ?
C13 C8 C7 121.1(3) . . ?
C9 C8 C7 120.4(3) . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
C2 C1 C6 121.4(4) . . ?
C2 C1 N1 118.1(3) . . ?
C6 C1 N1 120.5(3) . . ?
C14 N4 H2N 113(3) . . ?
C14 N4 H1N 118(4) . . ?
H2N N4 H1N 115(5) . . ?
O3 C14 N4 121.1(4) . . ?
O3 C14 N3 119.3(3) . . ?
N4 C14 N3 119.5(3) . . ?
O4 N5 O5 121.3(3) . . ?
O4 N5 O6 121.8(4) . . ?
O5 N5 O6 116.9(4) . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C12 C13 C8 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C9 C10 C11 120.4(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?

_refine_diff_density_max         0.699
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.093

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1982200'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-05-27 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         ?
_chemical_formula_sum            'C14 H12 N4 O3'
_chemical_formula_weight         284.28

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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.5740(15)
_cell_length_b                   10.7264(11)
_cell_length_c                   8.1105(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.563(5)
_cell_angle_gamma                90
_cell_volume                     1346.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17544
_cell_measurement_theta_min      3.162
_cell_measurement_theta_max      26.438

_exptl_crystal_description       block
_exptl_crystal_colour            ?


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   0.979
_exptl_transmission_factor_max   0.990
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.990

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.990

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17544
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.162
_diffrn_reflns_theta_max         26.438
_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             2760
_reflns_number_gt                1964
_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       'BRUKER SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 4.1.0'
_computing_publication_material  ?
_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+0.1885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0128(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2760
_refine_ls_number_parameters     203
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.57054(10) 0.39634(15) 0.39280(19) 0.0470(4) Uani 1 1 d . . . . .
C2 C 0.58919(10) 0.28243(15) 0.46485(19) 0.0487(4) Uani 1 1 d . . . . .
H2 H 0.5573 0.2121 0.4294 0.058 Uiso 1 1 calc R U . . .
C3 C 0.65609(9) 0.27453(14) 0.59075(18) 0.0431(4) Uani 1 1 d . . . . .
H3 H 0.6702 0.1975 0.6391 0.052 Uiso 1 1 calc R U . . .
C4 C 0.70293(9) 0.37932(13) 0.64701(18) 0.0388(3) Uani 1 1 d . . . . .
C5 C 0.68255(10) 0.49288(14) 0.5699(2) 0.0484(4) Uani 1 1 d . . . . .
H5 H 0.7136 0.5638 0.6058 0.058 Uiso 1 1 calc R U . . .
C6 C 0.61689(10) 0.50195(15) 0.4410(2) 0.0521(4) Uani 1 1 d . . . . .
H6 H 0.6043 0.5777 0.3879 0.063 Uiso 1 1 calc R U . . .
C7 C 0.77135(9) 0.37078(13) 0.78834(17) 0.0392(3) Uani 1 1 d . . . . .
C8 C 0.79251(9) 0.48291(13) 0.89295(19) 0.0428(4) Uani 1 1 d . . . . .
C9 C 0.72903(11) 0.53936(14) 0.9738(2) 0.0532(4) Uani 1 1 d . . . . .
H9 H 0.6731 0.5075 0.9614 0.064 Uiso 1 1 calc R U . . .
C10 C 0.74836(14) 0.64225(17) 1.0724(2) 0.0708(5) Uani 1 1 d . . . . .
H10 H 0.7057 0.6795 1.1270 0.085 Uiso 1 1 calc R U . . .
C11 C 0.83015(16) 0.68967(18) 1.0901(3) 0.0809(7) Uani 1 1 d . . . . .
H11 H 0.8430 0.7589 1.1576 0.097 Uiso 1 1 calc R U . . .
C12 C 0.89335(13) 0.63645(18) 1.0097(3) 0.0777(6) Uani 1 1 d . . . . .
H12 H 0.9488 0.6699 1.0220 0.093 Uiso 1 1 calc R U . . .
C13 C 0.87518(11) 0.53333(15) 0.9105(2) 0.0573(5) Uani 1 1 d . . . . .
H13 H 0.9182 0.4975 0.8554 0.069 Uiso 1 1 calc R U . . .
C14 C 0.91422(10) 0.14214(14) 0.9755(2) 0.0454(4) Uani 1 1 d . . . . .
N1 N 0.49925(10) 0.40523(17) 0.25903(19) 0.0619(4) Uani 1 1 d . . . . .
N2 N 0.80765(7) 0.26321(11) 0.81344(14) 0.0412(3) Uani 1 1 d . . . . .
N3 N 0.86783(8) 0.25025(12) 0.94683(16) 0.0454(3) Uani 1 1 d D . . . .
N4 N 0.89578(11) 0.04997(14) 0.8684(2) 0.0673(5) Uani 1 1 d . . . . .
O1 O 0.48898(10) 0.50316(16) 0.18473(19) 0.0950(5) Uani 1 1 d . . . . .
O2 O 0.45277(9) 0.31525(15) 0.22934(19) 0.0895(5) Uani 1 1 d . . . . .
O3 O 0.96963(7) 0.13821(10) 1.09480(15) 0.0587(3) Uani 1 1 d . . . . .
H1N H 0.9284(12) -0.0194(18) 0.876(2) 0.072(6) Uiso 1 1 d . . . . .
H2N H 0.8540(13) 0.0578(17) 0.796(2) 0.067(6) Uiso 1 1 d . . . . .
H3N H 0.8801(11) 0.3105(15) 1.020(2) 0.067(6) Uiso 1 1 d 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 1.371(2) . ?
C1 C6 1.376(2) . ?
C1 N1 1.464(2) . ?
C2 C3 1.376(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(2) . ?
C4 C7 1.476(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.2908(17) . ?
C7 C8 1.487(2) . ?
C8 C9 1.387(2) . ?
C8 C13 1.389(2) . ?
C9 C10 1.376(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O3 1.2216(18) . ?
C14 N4 1.326(2) . ?
C14 N3 1.3720(18) . ?
N1 O1 1.212(2) . ?
N1 O2 1.214(2) . ?
N2 N3 1.3551(17) . ?
N3 H3N 0.883(14) . ?
N4 H1N 0.90(2) . ?
N4 H2N 0.83(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
C2 C1 C6 122.28(15) . . ?
C2 C1 N1 118.66(15) . . ?
C6 C1 N1 119.05(15) . . ?
C1 C2 C3 118.48(15) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 121.26(14) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.53(14) . . ?
C3 C4 C7 120.69(13) . . ?
C5 C4 C7 120.76(13) . . ?
C6 C5 C4 120.95(14) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 118.45(14) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N2 C7 C4 116.25(13) . . ?
N2 C7 C8 124.64(13) . . ?
C4 C7 C8 119.09(12) . . ?
C9 C8 C13 118.96(15) . . ?
C9 C8 C7 119.97(13) . . ?
C13 C8 C7 121.06(14) . . ?
C10 C9 C8 120.32(16) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.00(19) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.60(19) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 120.20(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 119.91(17) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O3 C14 N4 125.02(14) . . ?
O3 C14 N3 118.30(14) . . ?
N4 C14 N3 116.67(15) . . ?
O1 N1 O2 123.26(17) . . ?
O1 N1 C1 118.07(17) . . ?
O2 N1 C1 118.66(16) . . ?
C7 N2 N3 117.91(12) . . ?
N2 N3 C14 121.64(13) . . ?
N2 N3 H3N 122.5(12) . . ?
C14 N3 H3N 115.9(12) . . ?
C14 N4 H1N 119.5(12) . . ?
C14 N4 H2N 118.9(13) . . ?
H1N N4 H2N 121.7(18) . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.033

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

