# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2073781'
loop_
_audit_author_name
_audit_author_address
'Roberto Centore'
;University of Naples Federico II
Italy
;
_audit_update_record             
;
2021-03-28 deposited with the CCDC.	2021-07-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
(E)-4,6-dimethoxy-5-(p-tolyldiazenyl)pyrimidin-2-amine
;
_chemical_name_common            'Polymorph I'
_chemical_formula_moiety         'C13 H15 N5 O2'
_chemical_formula_sum            'C13 H15 N5 O2'
_chemical_formula_weight         273.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.039(4)
_cell_length_b                   13.245(5)
_cell_length_c                   14.631(5)
_cell_angle_alpha                90
_cell_angle_beta                 132.51(2)
_cell_angle_gamma                90
_cell_volume                     1434.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    110
_cell_measurement_theta_min      3.191
_cell_measurement_theta_max      22.482

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2001)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;

_diffrn_reflns_number            14192
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.435
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3264
_reflns_number_gt                2008
_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       'Collect (Nonius, 1999)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_structure_solution    
;
SIR97 (Altomare et al., 1999)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 2012) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012) and
OLEX2 (Dolomanov et al., 2009)
;

_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)+(0.0985P)²+0.3347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.066(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3264
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1660
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.0222(4) -0.2081(3) 0.0091(3) 0.0967(10) Uani 1 1 d . . . . .
H1A H -0.102914 -0.194101 -0.060615 0.145 Uiso 1 1 calc R U . . .
H1B H 0.037822 -0.279218 0.026430 0.145 Uiso 1 1 calc R U . . .
H1C H 0.093348 -0.187532 -0.009494 0.145 Uiso 1 1 calc R U . . .
C2 C 0.0827(3) -0.1506(2) 0.1212(2) 0.0713(7) Uani 1 1 d . . . . .
C3 C 0.0568(4) -0.1887(2) 0.1954(3) 0.0795(8) Uani 1 1 d . . . . .
H3 H -0.002002 -0.250238 0.175151 0.095 Uiso 1 1 calc R U . . .
C4 C 0.1160(4) -0.1378(2) 0.2991(3) 0.0760(7) Uani 1 1 d . . . . .
H4 H 0.100642 -0.166149 0.349562 0.091 Uiso 1 1 calc R U . . .
C5 C 0.1980(3) -0.04481(18) 0.3284(2) 0.0591(6) Uani 1 1 d . . . . .
C6 C 0.2228(3) -0.0042(2) 0.2544(2) 0.0683(7) Uani 1 1 d . . . . .
H6 H 0.276633 0.058829 0.272612 0.082 Uiso 1 1 calc R U . . .
C7 C 0.1667(4) -0.0583(2) 0.1517(2) 0.0760(8) Uani 1 1 d . . . . .
H7 H 0.186341 -0.031476 0.102933 0.091 Uiso 1 1 calc R U . . .
C8 C 0.3746(3) 0.14188(16) 0.55969(18) 0.0503(5) Uani 1 1 d . . . . .
C9 C 0.3494(3) 0.11802(16) 0.64106(18) 0.0504(5) Uani 1 1 d . . . . .
C10 C 0.4862(3) 0.26256(16) 0.74863(18) 0.0517(5) Uani 1 1 d . . . . .
C11 C 0.4594(3) 0.23536(16) 0.58510(19) 0.0542(6) Uani 1 1 d . . . . .
C12 C 0.5647(6) 0.3612(2) 0.5320(3) 0.1117(14) Uani 1 1 d . . . . .
H12A H 0.566845 0.375620 0.468738 0.167 Uiso 1 1 calc R U . . .
H12B H 0.685948 0.360653 0.611517 0.167 Uiso 1 1 calc R U . . .
H12C H 0.495870 0.412168 0.531212 0.167 Uiso 1 1 calc R U . . .
C13 C 0.2050(4) 0.0170(2) 0.6870(3) 0.0832(8) Uani 1 1 d . . . . .
H13A H 0.128576 -0.041500 0.654730 0.125 Uiso 1 1 calc R U . . .
H13B H 0.139271 0.075102 0.677268 0.125 Uiso 1 1 calc R U . . .
H13C H 0.309006 0.006963 0.773389 0.125 Uiso 1 1 calc R U . . .
N1 N 0.2564(3) 0.00228(15) 0.43845(18) 0.0639(6) Uani 1 1 d . . . . .
N2 N 0.3184(3) 0.08903(14) 0.45603(16) 0.0549(5) Uani 1 1 d . . . . .
N3 N 0.4043(2) 0.17607(13) 0.73423(15) 0.0533(5) Uani 1 1 d . . . . .
N4 N 0.5154(3) 0.29610(13) 0.67671(16) 0.0574(5) Uani 1 1 d . . . . .
N5 N 0.5446(3) 0.32211(16) 0.84392(19) 0.0644(6) Uani 1 1 d . . . . .
H7A H 0.519(3) 0.306(2) 0.887(3) 0.077 Uiso 1 1 d . U . . .
H7B H 0.600(4) 0.382(2) 0.860(2) 0.077 Uiso 1 1 d . U . . .
O1 O 0.4831(3) 0.26451(12) 0.50905(15) 0.0734(6) Uani 1 1 d . . . . .
O2 O 0.2620(2) 0.03238(13) 0.62079(15) 0.0666(5) 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 1.514(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.372(4) . ?
C2 C7 1.378(4) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 N1 1.431(3) . ?
C6 C7 1.393(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N2 1.397(3) . ?
C8 C11 1.403(3) . ?
C8 C9 1.410(3) . ?
C9 N3 1.318(3) . ?
C9 O2 1.339(3) . ?
C10 N3 1.341(3) . ?
C10 N5 1.344(3) . ?
C10 N4 1.344(3) . ?
C11 N4 1.320(3) . ?
C11 O1 1.342(2) . ?
C12 O1 1.432(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O2 1.435(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 N2 1.248(3) . ?
N5 H7A 0.85(3) . ?
N5 H7B 0.90(3) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.1(2) . . ?
C3 C2 C1 121.4(3) . . ?
C7 C2 C1 120.5(3) . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 N1 124.2(2) . . ?
C4 C5 N1 116.4(2) . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 121.3(3) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
N2 C8 C11 117.21(18) . . ?
N2 C8 C9 129.3(2) . . ?
C11 C8 C9 113.40(18) . . ?
N3 C9 O2 118.50(18) . . ?
N3 C9 C8 123.6(2) . . ?
O2 C9 C8 117.85(19) . . ?
N3 C10 N5 117.12(19) . . ?
N3 C10 N4 126.44(18) . . ?
N5 C10 N4 116.4(2) . . ?
N4 C11 O1 118.3(2) . . ?
N4 C11 C8 124.93(19) . . ?
O1 C11 C8 116.74(18) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 N1 C5 113.63(19) . . ?
N1 N2 C8 117.64(18) . . ?
C9 N3 C10 116.39(17) . . ?
C11 N4 C10 115.2(2) . . ?
C10 N5 H7A 118.8(19) . . ?
C10 N5 H7B 123.3(17) . . ?
H7A N5 H7B 118(3) . . ?
C11 O1 C12 117.13(17) . . ?
C9 O2 C13 118.13(19) . . ?

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 C2 C3 C4 -1.4(4) . . . . ?
C1 C2 C3 C4 178.3(3) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C3 C4 C5 N1 -179.6(2) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
N1 C5 C6 C7 177.6(2) . . . . ?
C3 C2 C7 C6 -0.5(4) . . . . ?
C1 C2 C7 C6 179.8(2) . . . . ?
C5 C6 C7 C2 1.6(4) . . . . ?
N2 C8 C9 N3 -177.76(19) . . . . ?
C11 C8 C9 N3 -1.8(3) . . . . ?
N2 C8 C9 O2 1.1(3) . . . . ?
C11 C8 C9 O2 177.01(18) . . . . ?
N2 C8 C11 N4 177.8(2) . . . . ?
C9 C8 C11 N4 1.3(3) . . . . ?
N2 C8 C11 O1 -1.6(3) . . . . ?
C9 C8 C11 O1 -178.09(19) . . . . ?
C6 C5 N1 N2 6.2(3) . . . . ?
C4 C5 N1 N2 -175.4(2) . . . . ?
C5 N1 N2 C8 178.43(18) . . . . ?
C11 C8 N2 N1 174.3(2) . . . . ?
C9 C8 N2 N1 -9.9(3) . . . . ?
O2 C9 N3 C10 -178.00(18) . . . . ?
C8 C9 N3 C10 0.8(3) . . . . ?
N5 C10 N3 C9 -179.37(19) . . . . ?
N4 C10 N3 C9 0.9(3) . . . . ?
O1 C11 N4 C10 179.54(19) . . . . ?
C8 C11 N4 C10 0.1(3) . . . . ?
N3 C10 N4 C11 -1.4(3) . . . . ?
N5 C10 N4 C11 178.90(19) . . . . ?
N4 C11 O1 C12 -1.3(4) . . . . ?
C8 C11 O1 C12 178.2(3) . . . . ?
N3 C9 O2 C13 10.8(3) . . . . ?
C8 C9 O2 C13 -168.1(2) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.091


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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 2073786'
loop_
_audit_author_name
_audit_author_address
'Roberto Centore'
;University of Naples Federico II
Italy
;
_audit_update_record             
;
2021-03-28 deposited with the CCDC.	2021-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'(E)-4,6-dimethoxy-5-(p-tolyldiazenyl)pyrimidin-2-amine-co-methacrylic acid'
_chemical_formula_moiety         'C13 H15 N5 O2, C4 H6 O2'
_chemical_formula_sum            'C17 H21 N5 O4'
_chemical_formula_weight         359.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   6.8530(7)
_cell_length_b                   7.5100(16)
_cell_length_c                   17.512(3)
_cell_angle_alpha                95.142(15)
_cell_angle_beta                 92.063(14)
_cell_angle_gamma                93.937(14)
_cell_volume                     894.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    145
_cell_measurement_theta_min      3.769
_cell_measurement_theta_max      22.742

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2001)
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;

_diffrn_reflns_number            12221
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.338
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4017
_reflns_number_gt                2770
_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       'Collect (Nonius, 1999)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_structure_solution    
;
SIR97 (Altomare et al., 1999)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 2012) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012) and
OLEX2 (Dolomanov et al., 2009)
;

_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)+(0.0580P)²+0.2504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4017
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O1 O 0.25603(16) 0.31539(17) 0.61511(6) 0.0310(3) Uani 1 1 d . . . . .
O2 O -0.27967(15) 0.01186(17) 0.71501(6) 0.0304(3) Uani 1 1 d . . . . .
N1 N 0.0418(2) 0.1506(2) 0.79805(8) 0.0339(4) Uani 1 1 d . . . . .
N2 N 0.11461(19) 0.18866(19) 0.73615(7) 0.0270(3) Uani 1 1 d . . . . .
N3 N -0.01384(18) 0.22292(18) 0.53497(7) 0.0234(3) Uani 1 1 d . . . . .
N4 N -0.28982(18) 0.06526(19) 0.58783(7) 0.0244(3) Uani 1 1 d . . . . .
N5 N -0.2894(2) 0.1205(2) 0.46146(8) 0.0275(3) Uani 1 1 d . . . . .
H5A H -0.231(3) 0.162(3) 0.4189(11) 0.033 Uiso 1 1 d . U . . .
H5B H -0.405(3) 0.065(3) 0.4548(10) 0.033 Uiso 1 1 d . U . . .
C1 C 0.5676(4) 0.2627(3) 1.06363(12) 0.0593(7) Uani 1 1 d . . . . .
H1A H 0.648961 0.160582 1.065116 0.089 Uiso 1 1 calc R U . . .
H1B H 0.491037 0.272686 1.109826 0.089 Uiso 1 1 calc R U . . .
H1C H 0.651670 0.372915 1.061529 0.089 Uiso 1 1 calc R U . . .
C2 C 0.4306(3) 0.2346(3) 0.99338(10) 0.0408(5) Uani 1 1 d . . . . .
C3 C 0.5026(3) 0.2453(3) 0.92049(11) 0.0414(5) Uani 1 1 d . . . . .
H3 H 0.638956 0.271006 0.915345 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3801(3) 0.2194(3) 0.85551(10) 0.0348(4) Uani 1 1 d . . . . .
H4 H 0.432542 0.227991 0.806372 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1812(2) 0.1810(2) 0.86176(9) 0.0306(4) Uani 1 1 d . . . . .
C6 C 0.1085(3) 0.1682(3) 0.93369(10) 0.0498(6) Uani 1 1 d . . . . .
H6 H -0.027382 0.140338 0.938878 0.060 Uiso 1 1 calc R U . . .
C7 C 0.2333(3) 0.1959(3) 0.99845(10) 0.0533(6) Uani 1 1 d . . . . .
H7 H 0.180727 0.187856 1.047575 0.064 Uiso 1 1 calc R U . . .
C8 C -0.0049(2) 0.1649(2) 0.66914(8) 0.0238(4) Uani 1 1 d . . . . .
C9 C 0.0766(2) 0.2335(2) 0.60410(8) 0.0231(3) Uani 1 1 d . . . . .
C10 C -0.1951(2) 0.1365(2) 0.53001(8) 0.0228(3) Uani 1 1 d . . . . .
C11 C -0.1945(2) 0.0810(2) 0.65614(8) 0.0240(4) Uani 1 1 d . . . . .
C12 C -0.4737(2) -0.0764(3) 0.70175(9) 0.0325(4) Uani 1 1 d . . . . .
H12A H -0.470797 -0.175457 0.661490 0.049 Uiso 1 1 calc R U . . .
H12B H -0.564383 0.009779 0.685557 0.049 Uiso 1 1 calc R U . . .
H12C H -0.517458 -0.123178 0.749218 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3455(3) 0.3906(3) 0.55142(9) 0.0356(4) Uani 1 1 d . . . . .
H13A H 0.359410 0.295346 0.510337 0.053 Uiso 1 1 calc R U . . .
H13B H 0.474927 0.447509 0.567918 0.053 Uiso 1 1 calc R U . . .
H13C H 0.263312 0.480321 0.532458 0.053 Uiso 1 1 calc R U . . .
O3 O 0.12947(18) 0.73895(19) 0.66964(7) 0.0412(3) Uani 1 1 d . . . . .
O4 O -0.15235(18) 0.63662(19) 0.60926(7) 0.0371(3) Uani 1 1 d . . . . .
H4A H -0.102(3) 0.681(3) 0.5701(12) 0.045 Uiso 1 1 d . U . . .
C14 C -0.0319(2) 0.6637(2) 0.67125(9) 0.0274(4) Uani 1 1 d . . . . .
C15 C -0.1087(3) 0.5955(2) 0.74199(9) 0.0300(4) Uani 1 1 d . . . . .
C16 C -0.2837(3) 0.5100(3) 0.74196(11) 0.0448(5) Uani 1 1 d . . . . .
H16A H -0.363146 0.491142 0.695971 0.054 Uiso 1 1 calc R U . . .
H16B H -0.330156 0.467388 0.787937 0.054 Uiso 1 1 calc R U . . .
C17 C 0.0282(3) 0.6291(3) 0.81073(10) 0.0455(5) Uani 1 1 d . . . . .
H17A H 0.152942 0.578412 0.799165 0.068 Uiso 1 1 calc R U . . .
H17B H -0.029140 0.572459 0.853819 0.068 Uiso 1 1 calc R U . . .
H17C H 0.050620 0.758491 0.824376 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.3363(19) . ?
O1 C13 1.4328(19) . ?
O2 C11 1.3307(18) . ?
O2 C12 1.4458(19) . ?
N1 N2 1.2570(19) . ?
N1 C5 1.434(2) . ?
N2 C8 1.397(2) . ?
N3 C9 1.3334(19) . ?
N3 C10 1.358(2) . ?
N4 C11 1.3338(19) . ?
N4 C10 1.3525(19) . ?
N5 C10 1.334(2) . ?
N5 H5A 0.923(19) . ?
N5 H5B 0.87(2) . ?
C1 C2 1.511(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.371(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(2) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C11 1.406(2) . ?
C8 C9 1.409(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O3 C14 1.209(2) . ?
O4 C14 1.332(2) . ?
O4 H4A 0.86(2) . ?
C14 C15 1.482(2) . ?
C15 C16 1.321(3) . ?
C15 C17 1.491(2) . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C9 O1 C13 118.37(12) . . ?
C11 O2 C12 117.94(12) . . ?
N2 N1 C5 112.30(14) . . ?
N1 N2 C8 118.44(13) . . ?
C9 N3 C10 114.99(13) . . ?
C11 N4 C10 116.47(13) . . ?
C10 N5 H5A 121.4(11) . . ?
C10 N5 H5B 120.8(12) . . ?
H5A N5 H5B 117.7(16) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.60(16) . . ?
C7 C2 C1 121.95(19) . . ?
C3 C2 C1 120.45(19) . . ?
C4 C3 C2 121.40(18) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.18(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 118.89(16) . . ?
C6 C5 N1 116.50(16) . . ?
C4 C5 N1 124.61(15) . . ?
C5 C6 C7 120.22(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 121.71(18) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
N2 C8 C11 129.92(14) . . ?
N2 C8 C9 115.55(14) . . ?
C11 C8 C9 114.53(13) . . ?
N3 C9 O1 119.79(14) . . ?
N3 C9 C8 124.49(14) . . ?
O1 C9 C8 115.72(13) . . ?
N5 C10 N4 116.74(14) . . ?
N5 C10 N3 116.88(14) . . ?
N4 C10 N3 126.37(14) . . ?
O2 C11 N4 119.14(14) . . ?
O2 C11 C8 117.70(13) . . ?
N4 C11 C8 123.14(14) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 O4 H4A 111.9(14) . . ?
O3 C14 O4 121.96(15) . . ?
O3 C14 C15 122.43(15) . . ?
O4 C14 C15 115.61(15) . . ?
C16 C15 C14 121.36(16) . . ?
C16 C15 C17 124.09(16) . . ?
C14 C15 C17 114.54(15) . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C8 179.77(14) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C4 179.74(18) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C3 C4 C5 N1 -179.57(18) . . . . ?
N2 N1 C5 C6 170.86(17) . . . . ?
N2 N1 C5 C4 -9.9(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
N1 C5 C6 C7 -179.89(19) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
C1 C2 C7 C6 -179.2(2) . . . . ?
C5 C6 C7 C2 -0.7(4) . . . . ?
N1 N2 C8 C11 -9.3(3) . . . . ?
N1 N2 C8 C9 171.31(15) . . . . ?
C10 N3 C9 O1 179.79(13) . . . . ?
C10 N3 C9 C8 -1.0(2) . . . . ?
C13 O1 C9 N3 0.3(2) . . . . ?
C13 O1 C9 C8 -179.01(15) . . . . ?
N2 C8 C9 N3 179.56(14) . . . . ?
C11 C8 C9 N3 0.1(2) . . . . ?
N2 C8 C9 O1 -1.2(2) . . . . ?
C11 C8 C9 O1 179.37(14) . . . . ?
C11 N4 C10 N5 179.73(14) . . . . ?
C11 N4 C10 N3 -0.4(2) . . . . ?
C9 N3 C10 N5 -178.96(14) . . . . ?
C9 N3 C10 N4 1.2(2) . . . . ?
C12 O2 C11 N4 -0.5(2) . . . . ?
C12 O2 C11 C8 -179.28(15) . . . . ?
C10 N4 C11 O2 -179.32(14) . . . . ?
C10 N4 C11 C8 -0.6(2) . . . . ?
N2 C8 C11 O2 0.1(3) . . . . ?
C9 C8 C11 O2 179.47(14) . . . . ?
N2 C8 C11 N4 -178.60(15) . . . . ?
C9 C8 C11 N4 0.7(2) . . . . ?
O3 C14 C15 C16 -178.44(19) . . . . ?
O4 C14 C15 C16 1.6(2) . . . . ?
O3 C14 C15 C17 0.6(3) . . . . ?
O4 C14 C15 C17 -179.39(15) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/heptane'
####################################################################### 
# 
# 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 2073783'
loop_
_audit_author_name
_audit_author_address
'Roberto Centore'
;University of Naples Federico II
Italy
;
_audit_update_record             
;
2021-03-28 deposited with the CCDC.	2021-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(E)-4,6-dimethoxy-5-(p-methoxyphenyldiazenyl)pyrimidin-2-amine
_chemical_formula_moiety         'C13 H15 N5 O3'
_chemical_formula_sum            'C13 H15 N5 O3'
_chemical_formula_weight         289.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7630(16)
_cell_length_b                   13.552(4)
_cell_length_c                   30.386(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5667(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    163
_cell_measurement_theta_min      3.046
_cell_measurement_theta_max      22.914

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2001)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;

_diffrn_reflns_number            37423
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6430
_reflns_number_gt                4136
_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       'Collect (Nonius, 1999)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_structure_solution    
;
SIR97 (Altomare et al., 1999)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 2012) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012) and
OLEX2 (Dolomanov et al., 2009)
;


_refine_special_details          
;
The structure shows positional disorder of the 4-methoxyphenylazo 
group in one of the two crystallographically independent molecules, 
which is typical of azocompounds ("pedal motion"). The two split 
positions have different occupation factors, with the minor component 
having s.o.f. of 0.1747(17). For this reason, the anisotropic displacement 
parameters for the atoms of the minor component were not refined, but were 
set equal to those of the corresponding atoms of the major component. 
Moreover, some restraints on bond lenghts and angles were applied.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+2.0098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0049(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6430
_refine_ls_number_parameters     452
_refine_ls_number_restraints     153
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.086
_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
O1A O 0.14294(13) 0.19961(10) 0.96552(5) 0.0687(5) Uani 1 1 d D . . . .
N1A N 0.12288(13) 0.59074(12) 0.91029(6) 0.0531(4) Uani 1 1 d D . . . .
N2A N 0.11093(12) 0.65501(11) 0.93904(5) 0.0479(4) Uani 1 1 d D . . . .
C1A C 0.1514(2) 0.17118(17) 1.01010(9) 0.0791(8) Uani 1 1 d D . . . .
H1A H 0.158397 0.100812 1.011883 0.119 Uiso 1 1 calc R U . . .
H1B H 0.094208 0.191102 1.025843 0.119 Uiso 1 1 calc R U . . .
H1C H 0.207384 0.202310 1.022850 0.119 Uiso 1 1 calc R U . . .
C2A C 0.13835(15) 0.29842(13) 0.95561(7) 0.0489(5) Uani 1 1 d D . . . .
C3A C 0.12241(17) 0.37196(15) 0.98573(7) 0.0579(6) Uani 1 1 d D . . . .
H3A H 0.114761 0.356830 1.015379 0.069 Uiso 1 1 calc R U . . .
C4A C 0.11778(16) 0.46945(14) 0.97153(7) 0.0546(5) Uani 1 1 d D . . . .
H4A H 0.107422 0.519546 0.991914 0.066 Uiso 1 1 calc R U . . .
C5A C 0.12831(14) 0.49267(13) 0.92777(6) 0.0456(5) Uani 1 1 d D . . . .
C6A C 0.14422(16) 0.41774(15) 0.89787(7) 0.0553(5) Uani 1 1 d D . . . .
H6A H 0.151177 0.432713 0.868168 0.066 Uiso 1 1 calc R U . . .
C7A C 0.14987(17) 0.32133(14) 0.91150(7) 0.0569(6) Uani 1 1 d D . . . .
H7A H 0.161431 0.271466 0.891140 0.068 Uiso 1 1 calc R U . . .
C8A C 0.10403(14) 0.75316(13) 0.92532(6) 0.0435(4) Uani 1 1 d D . . . .
C9A C 0.11008(14) 0.82616(14) 0.95829(6) 0.0444(5) Uani 1 1 d D . . . .
C10A C 0.09558(15) 0.94830(13) 0.90859(7) 0.0485(5) Uani 1 1 d D . . . .
C11A C 0.08839(14) 0.79180(13) 0.88293(6) 0.0460(5) Uani 1 1 d D . . . .
C12A C 0.0500(2) 0.76987(18) 0.80740(7) 0.0777(8) Uani 1 1 d D . . . .
H12A H 0.050432 0.718639 0.785585 0.117 Uiso 1 1 calc R U . . .
H12B H 0.096288 0.819810 0.799527 0.117 Uiso 1 1 calc R U . . .
H12C H -0.013709 0.798543 0.808989 0.117 Uiso 1 1 calc R U . . .
C13A C 0.1219(2) 0.86888(17) 1.03373(7) 0.0749(8) Uani 1 1 d D . . . .
H13A H 0.178551 0.909378 1.030024 0.112 Uiso 1 1 calc R U . . .
H13B H 0.124096 0.837430 1.062019 0.112 Uiso 1 1 calc R U . . .
H13C H 0.064712 0.909187 1.031786 0.112 Uiso 1 1 calc R U . . .
O2A O 0.07536(13) 0.72878(10) 0.84958(4) 0.0628(4) Uani 1 1 d D . . . .
O3A O 0.11947(12) 0.79491(10) 0.99979(4) 0.0594(4) Uani 1 1 d D . . . .
N3A N 0.10683(12) 0.92197(11) 0.95097(5) 0.0476(4) Uani 1 1 d D . . . .
N4A N 0.08346(13) 0.88720(11) 0.87428(5) 0.0529(4) Uani 1 1 d D . . . .
N5A N 0.09469(16) 1.04472(12) 0.89995(6) 0.0703(6) Uani 1 1 d D . . . .
H5A H 0.086620 1.065037 0.873384 0.084 Uiso 1 1 calc R U . . .
H5B H 0.102198 1.086608 0.920931 0.084 Uiso 1 1 calc R U . . .
O1B O 0.88764(14) 0.49325(14) 0.90918(7) 0.0677(5) Uani 0.8253(17) 1 d D . P A
1
N1B N 0.61051(14) 0.72004(15) 0.82200(6) 0.0456(5) Uani 0.8253(17) 1 d D . P A
1
N2B N 0.52294(17) 0.68975(15) 0.82073(7) 0.0455(5) Uani 0.8253(17) 1 d D . P A
1
C1B C 0.8812(3) 0.3901(2) 0.91612(14) 0.0682(9) Uani 0.8253(17) 1 d D . P A 1
H1D H 0.875376 0.357137 0.888284 0.102 Uiso 0.8253(17) 1 calc R U P A 1
H1E H 0.825208 0.375791 0.933849 0.102 Uiso 0.8253(17) 1 calc R U P A 1
H1F H 0.938638 0.367499 0.930937 0.102 Uiso 0.8253(17) 1 calc R U P A 1
C2B C 0.81431(18) 0.5409(2) 0.88726(9) 0.0509(6) Uani 0.8253(17) 1 d D . P A 1
C3B C 0.7267(2) 0.4982(2) 0.87599(10) 0.0576(8) Uani 0.8253(17) 1 d D . P A 1
H3B H 0.713641 0.432515 0.882520 0.069 Uiso 0.8253(17) 1 calc R U P A 1
C4B C 0.6571(2) 0.5583(2) 0.85402(10) 0.0615(7) Uani 0.8253(17) 1 d D . P A 1
H4B H 0.597143 0.531722 0.846334 0.074 Uiso 0.8253(17) 1 calc R U P A 1
C5B C 0.6773(2) 0.6556(2) 0.84396(10) 0.0523(7) Uani 0.8253(17) 1 d D . P A 1
C6B C 0.7667(2) 0.6931(2) 0.85557(10) 0.0629(8) Uani 0.8253(17) 1 d D . P A 1
H6B H 0.781613 0.758078 0.848363 0.075 Uiso 0.8253(17) 1 calc R U P A 1
C7B C 0.8334(2) 0.6381(2) 0.87717(10) 0.0644(8) Uani 0.8253(17) 1 d D . P A 1
H7B H 0.892517 0.666057 0.885251 0.077 Uiso 0.8253(17) 1 calc R U P A 1
C8B C 0.4541(2) 0.7473(3) 0.79981(16) 0.0379(7) Uani 0.8253(17) 1 d D . P A 1
C9B C 0.3637(4) 0.7019(4) 0.7910(3) 0.0429(8) Uani 0.8253(17) 1 d D . P A 1
C10B C 0.3122(10) 0.8332(7) 0.7525(6) 0.0444(7) Uani 0.8253(17) 1 d D . P A 1
C11B C 0.4593(4) 0.8459(2) 0.7855(3) 0.0383(7) Uani 0.8253(17) 1 d D . P A 1
C12B C 0.5322(3) 1.0066(3) 0.78874(12) 0.0689(12) Uani 0.8253(17) 1 d D . P A 1
H12D H 0.519492 1.018313 0.758111 0.103 Uiso 0.8253(17) 1 calc R U P A 1
H12E H 0.593044 1.036315 0.796678 0.103 Uiso 0.8253(17) 1 calc R U P A 1
H12F H 0.481062 1.035050 0.806101 0.103 Uiso 0.8253(17) 1 calc R U P A 1
C13B C 0.2564(6) 0.5661(7) 0.8023(5) 0.0741(11) Uani 0.8253(17) 1 d D . P A 1
H13D H 0.236417 0.571363 0.772116 0.111 Uiso 0.8253(17) 1 calc R U P A 1
H13E H 0.210149 0.599328 0.820744 0.111 Uiso 0.8253(17) 1 calc R U P A 1
H13F H 0.259807 0.497789 0.810493 0.111 Uiso 0.8253(17) 1 calc R U P A 1
O2B O 0.5367(3) 0.89967(19) 0.79690(19) 0.0514(7) Uani 0.8253(17) 1 d D . P A 1
O3B O 0.3513(3) 0.6113(3) 0.80765(19) 0.0574(8) Uani 0.8253(17) 1 d D . P A 1
N3B N 0.2932(4) 0.7424(5) 0.7681(3) 0.0481(11) Uani 0.8253(17) 1 d D . P A 1
N4B N 0.3894(5) 0.8891(3) 0.7629(3) 0.0424(7) Uani 0.8253(17) 1 d D . P A 1
N5B N 0.2453(7) 0.8736(8) 0.7262(3) 0.0586(15) Uani 0.8253(17) 1 d D . P A 1
H5C H 0.252894 0.932962 0.716755 0.070 Uiso 0.8253(17) 1 calc R U P A 1
H5D H 0.194768 0.840348 0.718709 0.070 Uiso 0.8253(17) 1 calc R U P A 1
O1C O 0.8062(6) 0.4158(6) 0.9065(3) 0.0677(5) Uani 0.1747(17) 1 d D . P A 2
N1C N 0.5452(7) 0.6470(7) 0.8277(3) 0.0456(5) Uani 0.1747(17) 1 d D . P A 2
N2C N 0.5449(10) 0.7297(7) 0.8156(4) 0.0455(5) Uani 0.1747(17) 1 d D . P A 2
C1C C 0.9074(10) 0.4260(15) 0.9122(8) 0.0682(9) Uani 0.1747(17) 1 d D . P A 2
H1C1 H 0.932090 0.370082 0.928029 0.102 Uiso 0.1747(17) 1 calc R U P A 2
H1C2 H 0.938283 0.429688 0.883903 0.102 Uiso 0.1747(17) 1 calc R U P A 2
H1C3 H 0.920732 0.485180 0.928467 0.102 Uiso 0.1747(17) 1 calc R U P A 2
C2C C 0.7620(10) 0.4925(11) 0.8840(6) 0.0509(6) Uani 0.1747(17) 1 d D . P A 2
C3C C 0.6645(9) 0.4695(9) 0.8745(4) 0.0576(8) Uani 0.1747(17) 1 d D . P A 2
H3C H 0.639266 0.409500 0.884028 0.069 Uiso 0.1747(17) 1 calc R U P A 2
C4C C 0.6092(10) 0.5295(9) 0.8531(5) 0.0615(7) Uani 0.1747(17) 1 d D . P A 2
H4C H 0.547650 0.509793 0.843998 0.074 Uiso 0.1747(17) 1 calc R U P A 2
C5C C 0.6418(8) 0.6212(10) 0.8441(6) 0.0523(7) Uani 0.1747(17) 1 d D . P A 2
C6C C 0.7367(10) 0.6442(11) 0.8486(5) 0.0629(8) Uani 0.1747(17) 1 d D . P A 2
H6C H 0.759696 0.703715 0.837505 0.075 Uiso 0.1747(17) 1 calc R U P A 2
C7C C 0.8009(10) 0.5800(10) 0.8697(5) 0.0644(8) Uani 0.1747(17) 1 d D . P A 2
H7C H 0.866094 0.595614 0.873769 0.077 Uiso 0.1747(17) 1 calc R U P A 2
C8C C 0.4633(13) 0.7664(14) 0.7940(10) 0.0379(7) Uani 0.1747(17) 1 d D . P A 2
C9C C 0.377(2) 0.715(2) 0.7882(16) 0.0429(8) Uani 0.1747(17) 1 d D . P A 2
C10C C 0.313(5) 0.845(4) 0.751(3) 0.0444(7) Uani 0.1747(17) 1 d D . P A 2
C11C C 0.4548(19) 0.8664(14) 0.7843(14) 0.0383(7) Uani 0.1747(17) 1 d D . P A 2
C12C C 0.5389(19) 1.0096(16) 0.7697(7) 0.0689(12) Uani 0.1747(17) 1 d D . P A 2
H12G H 0.545127 0.992205 0.739172 0.103 Uiso 0.1747(17) 1 calc R U P A 2
H12H H 0.594693 1.047116 0.778643 0.103 Uiso 0.1747(17) 1 calc R U P A 2
H12I H 0.481306 1.048468 0.773762 0.103 Uiso 0.1747(17) 1 calc R U P A 2
C13C C 0.273(3) 0.576(4) 0.800(3) 0.0741(11) Uani 0.1747(17) 1 d D . P A 2
H13G H 0.242209 0.590086 0.772238 0.111 Uiso 0.1747(17) 1 calc R U P A 2
H13H H 0.232701 0.599781 0.823468 0.111 Uiso 0.1747(17) 1 calc R U P A 2
H13I H 0.280345 0.505418 0.802856 0.111 Uiso 0.1747(17) 1 calc R U P A 2
O2C O 0.5325(17) 0.9218(13) 0.7956(10) 0.0514(7) Uani 0.1747(17) 1 d D . P A 2
O3C O 0.367(2) 0.6227(19) 0.8017(11) 0.0574(8) Uani 0.1747(17) 1 d D . P A 2
N3C N 0.304(2) 0.750(3) 0.7636(17) 0.0481(11) Uani 0.1747(17) 1 d D . P A 2
N4C N 0.388(2) 0.9070(19) 0.7593(15) 0.0424(7) Uani 0.1747(17) 1 d D . P A 2
N5C N 0.252(4) 0.877(4) 0.7201(18) 0.0586(15) Uani 0.1747(17) 1 d D . P A 2
H5E H 0.209000 0.838067 0.709015 0.070 Uiso 0.1747(17) 1 calc R U P A 2
H5F H 0.254814 0.937518 0.711289 0.070 Uiso 0.1747(17) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C2A 1.374(2) . ?
O1A C1A 1.413(3) . ?
N1A N2A 1.245(2) . ?
N1A C5A 1.433(2) . ?
N2A C8A 1.397(2) . ?
C1A H1A 0.9600 . ?
C1A H1B 0.9600 . ?
C1A H1C 0.9600 . ?
C2A C3A 1.371(3) . ?
C2A C7A 1.385(3) . ?
C3A C4A 1.391(3) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.374(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.380(3) . ?
C6A C7A 1.373(3) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C8A C11A 1.407(3) . ?
C8A C9A 1.411(3) . ?
C9A N3A 1.318(2) . ?
C9A O3A 1.336(2) . ?
C10A N5A 1.333(2) . ?
C10A N4A 1.342(2) . ?
C10A N3A 1.345(2) . ?
C11A N4A 1.321(2) . ?
C11A O2A 1.337(2) . ?
C12A O2A 1.440(2) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A O3A 1.439(2) . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
N5A H5A 0.8600 . ?
N5A H5B 0.8600 . ?
O1B C2B 1.371(3) . ?
O1B C1B 1.416(3) . ?
N1B N2B 1.274(3) . ?
N1B C5B 1.433(3) . ?
N2B C8B 1.382(3) . ?
C1B H1D 0.9600 . ?
C1B H1E 0.9600 . ?
C1B H1F 0.9600 . ?
C2B C7B 1.378(4) . ?
C2B C3B 1.380(4) . ?
C3B C4B 1.424(4) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.381(4) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.377(4) . ?
C6B C7B 1.353(4) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
C8B C11B 1.406(4) . ?
C8B C9B 1.414(4) . ?
C9B N3B 1.314(4) . ?
C9B O3B 1.340(3) . ?
C10B N5B 1.336(5) . ?
C10B N4B 1.343(4) . ?
C10B N3B 1.344(5) . ?
C11B N4B 1.319(3) . ?
C11B O2B 1.337(3) . ?
C12B O2B 1.472(4) . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B O3B 1.452(4) . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
N5B H5C 0.8600 . ?
N5B H5D 0.8600 . ?
O1C C2C 1.387(11) . ?
O1C C1C 1.410(13) . ?
N1C N2C 1.181(11) . ?
N1C C5C 1.461(12) . ?
N2C C8C 1.392(13) . ?
C1C H1C1 0.9600 . ?
C1C H1C2 0.9600 . ?
C1C H1C3 0.9600 . ?
C2C C7C 1.372(14) . ?
C2C C3C 1.407(13) . ?
C3C C4C 1.290(12) . ?
C3C H3C 0.9300 . ?
C4C C5C 1.350(13) . ?
C4C H4C 0.9300 . ?
C5C C6C 1.350(13) . ?
C6C C7C 1.395(13) . ?
C6C H6C 0.9300 . ?
C7C H7C 0.9300 . ?
C8C C9C 1.392(14) . ?
C8C C11C 1.393(13) . ?
C9C O3C 1.324(14) . ?
C9C N3C 1.334(14) . ?
C10C N5C 1.339(16) . ?
C10C N3C 1.343(15) . ?
C10C N4C 1.357(15) . ?
C11C N4C 1.315(14) . ?
C11C O2C 1.351(14) . ?
C12C O2C 1.430(15) . ?
C12C H12G 0.9600 . ?
C12C H12H 0.9600 . ?
C12C H12I 0.9600 . ?
C13C O3C 1.449(16) . ?
C13C H13G 0.9600 . ?
C13C H13H 0.9600 . ?
C13C H13I 0.9600 . ?
N5C H5E 0.8600 . ?
N5C H5F 0.8600 . ?

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
C2A O1A C1A 118.66(17) . . ?
N2A N1A C5A 113.31(16) . . ?
N1A N2A C8A 117.76(16) . . ?
O1A C1A H1A 109.5 . . ?
O1A C1A H1B 109.5 . . ?
H1A C1A H1B 109.5 . . ?
O1A C1A H1C 109.5 . . ?
H1A C1A H1C 109.5 . . ?
H1B C1A H1C 109.5 . . ?
C3A C2A O1A 124.73(19) . . ?
C3A C2A C7A 120.09(18) . . ?
O1A C2A C7A 115.17(18) . . ?
C2A C3A C4A 119.4(2) . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A H3A 120.3 . . ?
C5A C4A C3A 120.85(19) . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
C4A C5A C6A 119.03(18) . . ?
C4A C5A N1A 124.44(17) . . ?
C6A C5A N1A 116.53(18) . . ?
C7A C6A C5A 120.7(2) . . ?
C7A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
C6A C7A C2A 119.93(19) . . ?
C6A C7A H7A 120.0 . . ?
C2A C7A H7A 120.0 . . ?
N2A C8A C11A 129.64(17) . . ?
N2A C8A C9A 116.85(16) . . ?
C11A C8A C9A 113.47(16) . . ?
N3A C9A O3A 118.35(17) . . ?
N3A C9A C8A 124.68(17) . . ?
O3A C9A C8A 116.98(16) . . ?
N5A C10A N4A 116.80(18) . . ?
N5A C10A N3A 116.72(18) . . ?
N4A C10A N3A 126.47(17) . . ?
N4A C11A O2A 117.87(17) . . ?
N4A C11A C8A 123.65(17) . . ?
O2A C11A C8A 118.46(16) . . ?
O2A C12A H12A 109.5 . . ?
O2A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
O2A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O3A C13A H13A 109.5 . . ?
O3A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
O3A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11A O2A C12A 117.38(16) . . ?
C9A O3A C13A 117.24(16) . . ?
C9A N3A C10A 115.27(16) . . ?
C11A N4A C10A 116.30(16) . . ?
C10A N5A H5A 120.0 . . ?
C10A N5A H5B 120.0 . . ?
H5A N5A H5B 120.0 . . ?
C2B O1B C1B 119.4(2) . . ?
N2B N1B C5B 115.1(2) . . ?
N1B N2B C8B 118.7(2) . . ?
O1B C1B H1D 109.5 . . ?
O1B C1B H1E 109.5 . . ?
H1D C1B H1E 109.5 . . ?
O1B C1B H1F 109.5 . . ?
H1D C1B H1F 109.5 . . ?
H1E C1B H1F 109.5 . . ?
O1B C2B C7B 114.7(2) . . ?
O1B C2B C3B 124.5(3) . . ?
C7B C2B C3B 120.8(3) . . ?
C2B C3B C4B 117.7(3) . . ?
C2B C3B H3B 121.2 . . ?
C4B C3B H3B 121.2 . . ?
C5B C4B C3B 120.9(3) . . ?
C5B C4B H4B 119.6 . . ?
C3B C4B H4B 119.6 . . ?
C6B C5B C4B 118.4(3) . . ?
C6B C5B N1B 117.9(2) . . ?
C4B C5B N1B 123.7(3) . . ?
C7B C6B C5B 121.8(3) . . ?
C7B C6B H6B 119.1 . . ?
C5B C6B H6B 119.1 . . ?
C6B C7B C2B 120.3(3) . . ?
C6B C7B H7B 119.8 . . ?
C2B C7B H7B 119.8 . . ?
N2B C8B C11B 130.1(3) . . ?
N2B C8B C9B 116.4(3) . . ?
C11B C8B C9B 113.5(3) . . ?
N3B C9B O3B 119.3(3) . . ?
N3B C9B C8B 124.7(3) . . ?
O3B C9B C8B 116.0(3) . . ?
N5B C10B N4B 117.0(4) . . ?
N5B C10B N3B 116.9(5) . . ?
N4B C10B N3B 126.0(4) . . ?
N4B C11B O2B 118.3(3) . . ?
N4B C11B C8B 123.1(3) . . ?
O2B C11B C8B 118.6(3) . . ?
O2B C12B H12D 109.5 . . ?
O2B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
O2B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
O3B C13B H13D 109.5 . . ?
O3B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
O3B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C11B O2B C12B 117.4(3) . . ?
C9B O3B C13B 117.3(5) . . ?
C9B N3B C10B 115.1(4) . . ?
C11B N4B C10B 116.7(3) . . ?
C10B N5B H5C 120.0 . . ?
C10B N5B H5D 120.0 . . ?
H5C N5B H5D 120.0 . . ?
C2C O1C C1C 114.9(11) . . ?
N2C N1C C5C 109.6(10) . . ?
N1C N2C C8C 119.2(12) . . ?
O1C C1C H1C1 109.5 . . ?
O1C C1C H1C2 109.5 . . ?
H1C1 C1C H1C2 109.5 . . ?
O1C C1C H1C3 109.5 . . ?
H1C1 C1C H1C3 109.5 . . ?
H1C2 C1C H1C3 109.5 . . ?
C7C C2C O1C 129.3(12) . . ?
C7C C2C C3C 120.0(10) . . ?
O1C C2C C3C 110.7(11) . . ?
C4C C3C C2C 121.7(12) . . ?
C4C C3C H3C 119.1 . . ?
C2C C3C H3C 119.1 . . ?
C3C C4C C5C 119.1(12) . . ?
C3C C4C H4C 120.4 . . ?
C5C C4C H4C 120.4 . . ?
C4C C5C C6C 120.9(11) . . ?
C4C C5C N1C 89.2(9) . . ?
C6C C5C N1C 149.3(12) . . ?
C5C C6C C7C 121.1(12) . . ?
C5C C6C H6C 119.5 . . ?
C7C C6C H6C 119.5 . . ?
C2C C7C C6C 115.9(12) . . ?
C2C C7C H7C 122.1 . . ?
C6C C7C H7C 122.1 . . ?
C9C C8C N2C 125.0(14) . . ?
C9C C8C C11C 112.8(15) . . ?
N2C C8C C11C 121.0(14) . . ?
O3C C9C N3C 115.8(18) . . ?
O3C C9C C8C 121.3(18) . . ?
N3C C9C C8C 122.3(17) . . ?
N5C C10C N3C 117(3) . . ?
N5C C10C N4C 114(2) . . ?
N3C C10C N4C 128(2) . . ?
N4C C11C O2C 118.0(16) . . ?
N4C C11C C8C 126.0(17) . . ?
O2C C11C C8C 114.9(15) . . ?
O2C C12C H12G 109.5 . . ?
O2C C12C H12H 109.5 . . ?
H12G C12C H12H 109.5 . . ?
O2C C12C H12I 109.5 . . ?
H12G C12C H12I 109.5 . . ?
H12H C12C H12I 109.5 . . ?
O3C C13C H13G 109.5 . . ?
O3C C13C H13H 109.5 . . ?
H13G C13C H13H 109.5 . . ?
O3C C13C H13I 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
C11C O2C C12C 111.8(18) . . ?
C9C O3C C13C 120(2) . . ?
C9C N3C C10C 115.6(18) . . ?
C11C N4C C10C 112.3(17) . . ?
C10C N5C H5E 120.0 . . ?
C10C N5C H5F 120.0 . . ?
H5E N5C H5F 120.0 . . ?

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
C5A N1A N2A C8A -179.57(16) . . . . ?
C1A O1A C2A C3A -13.3(3) . . . . ?
C1A O1A C2A C7A 167.5(2) . . . . ?
O1A C2A C3A C4A -179.0(2) . . . . ?
C7A C2A C3A C4A 0.1(3) . . . . ?
C2A C3A C4A C5A 0.4(3) . . . . ?
C3A C4A C5A C6A -0.4(3) . . . . ?
C3A C4A C5A N1A 178.9(2) . . . . ?
N2A N1A C5A C4A 2.5(3) . . . . ?
N2A N1A C5A C6A -178.27(19) . . . . ?
C4A C5A C6A C7A -0.3(3) . . . . ?
N1A C5A C6A C7A -179.6(2) . . . . ?
C5A C6A C7A C2A 0.8(3) . . . . ?
C3A C2A C7A C6A -0.7(3) . . . . ?
O1A C2A C7A C6A 178.4(2) . . . . ?
N1A N2A C8A C11A 14.7(3) . . . . ?
N1A N2A C8A C9A -167.68(18) . . . . ?
N2A C8A C9A N3A 178.61(18) . . . . ?
C11A C8A C9A N3A -3.4(3) . . . . ?
N2A C8A C9A O3A -1.6(3) . . . . ?
C11A C8A C9A O3A 176.38(18) . . . . ?
N2A C8A C11A N4A -179.90(19) . . . . ?
C9A C8A C11A N4A 2.4(3) . . . . ?
N2A C8A C11A O2A 1.8(3) . . . . ?
C9A C8A C11A O2A -175.84(18) . . . . ?
N4A C11A O2A C12A -4.4(3) . . . . ?
C8A C11A O2A C12A 174.0(2) . . . . ?
N3A C9A O3A C13A 2.1(3) . . . . ?
C8A C9A O3A C13A -177.7(2) . . . . ?
O3A C9A N3A C10A -178.87(18) . . . . ?
C8A C9A N3A C10A 0.9(3) . . . . ?
N5A C10A N3A C9A -178.22(19) . . . . ?
N4A C10A N3A C9A 3.0(3) . . . . ?
O2A C11A N4A C10A 179.14(19) . . . . ?
C8A C11A N4A C10A 0.8(3) . . . . ?
N5A C10A N4A C11A 177.3(2) . . . . ?
N3A C10A N4A C11A -3.9(3) . . . . ?
C5B N1B N2B C8B -179.5(3) . . . . ?
C1B O1B C2B C7B -171.8(3) . . . . ?
C1B O1B C2B C3B 8.9(4) . . . . ?
O1B C2B C3B C4B 178.7(3) . . . . ?
C7B C2B C3B C4B -0.5(4) . . . . ?
C2B C3B C4B C5B 0.7(4) . . . . ?
C3B C4B C5B C6B 0.2(4) . . . . ?
C3B C4B C5B N1B -179.9(3) . . . . ?
N2B N1B C5B C6B -165.1(2) . . . . ?
N2B N1B C5B C4B 15.0(4) . . . . ?
C4B C5B C6B C7B -1.4(4) . . . . ?
N1B C5B C6B C7B 178.6(3) . . . . ?
C5B C6B C7B C2B 1.7(5) . . . . ?
O1B C2B C7B C6B -180.0(3) . . . . ?
C3B C2B C7B C6B -0.7(4) . . . . ?
N1B N2B C8B C11B -13.0(8) . . . . ?
N1B N2B C8B C9B 166.9(5) . . . . ?
N2B C8B C9B N3B -173.8(9) . . . . ?
C11B C8B C9B N3B 6.1(13) . . . . ?
N2B C8B C9B O3B 6.3(11) . . . . ?
C11B C8B C9B O3B -173.8(8) . . . . ?
N2B C8B C11B N4B 174.9(7) . . . . ?
C9B C8B C11B N4B -5.0(12) . . . . ?
N2B C8B C11B O2B -8.2(11) . . . . ?
C9B C8B C11B O2B 171.8(7) . . . . ?
N4B C11B O2B C12B 8.1(11) . . . . ?
C8B C11B O2B C12B -168.9(6) . . . . ?
N3B C9B O3B C13B -4.9(14) . . . . ?
C8B C9B O3B C13B 175.0(9) . . . . ?
O3B C9B N3B C10B -179.7(14) . . . . ?
C8B C9B N3B C10B 0.4(19) . . . . ?
N5B C10B N3B C9B 174.9(15) . . . . ?
N4B C10B N3B C9B -9(3) . . . . ?
O2B C11B N4B C10B -179.2(13) . . . . ?
C8B C11B N4B C10B -2.3(17) . . . . ?
N5B C10B N4B C11B -173.9(15) . . . . ?
N3B C10B N4B C11B 10(3) . . . . ?
C5C N1C N2C C8C 172.7(19) . . . . ?
C1C O1C C2C C7C -6(3) . . . . ?
C1C O1C C2C C3C 171.7(16) . . . . ?
C7C C2C C3C C4C -1(3) . . . . ?
O1C C2C C3C C4C -178.9(13) . . . . ?
C2C C3C C4C C5C -8(2) . . . . ?
C3C C4C C5C C6C 14(3) . . . . ?
C3C C4C C5C N1C -172.1(14) . . . . ?
N2C N1C C5C C4C -179.8(13) . . . . ?
N2C N1C C5C C6C -10(4) . . . . ?
C4C C5C C6C C7C -11(3) . . . . ?
N1C C5C C6C C7C -179(2) . . . . ?
O1C C2C C7C C6C -178.4(17) . . . . ?
C3C C2C C7C C6C 4(3) . . . . ?
C5C C6C C7C C2C 2(3) . . . . ?
N1C N2C C8C C9C 5(5) . . . . ?
N1C N2C C8C C11C 171(3) . . . . ?
N2C C8C C9C O3C -3(7) . . . . ?
C11C C8C C9C O3C -170(5) . . . . ?
N2C C8C C9C N3C -173(4) . . . . ?
C11C C8C C9C N3C 19(7) . . . . ?
C9C C8C C11C N4C -22(7) . . . . ?
N2C C8C C11C N4C 170(4) . . . . ?
C9C C8C C11C O2C 171(4) . . . . ?
N2C C8C C11C O2C 3(6) . . . . ?
N4C C11C O2C C12C -13(6) . . . . ?
C8C C11C O2C C12C 155(3) . . . . ?
N3C C9C O3C C13C -16(8) . . . . ?
C8C C9C O3C C13C 173(5) . . . . ?
O3C C9C N3C C10C 178(7) . . . . ?
C8C C9C N3C C10C -11(10) . . . . ?
N5C C10C N3C C9C 168(8) . . . . ?
N4C C10C N3C C9C 3(15) . . . . ?
O2C C11C N4C C10C -179(6) . . . . ?
C8C C11C N4C C10C 14(9) . . . . ?
N5C C10C N4C C11C -170(7) . . . . ?
N3C C10C N4C C11C -4(14) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2073785'
loop_
_audit_author_name
_audit_author_address
'Roberto Centore'
;University of Naples Federico II
Italy
;
_audit_update_record             
;
2021-03-28 deposited with the CCDC.	2021-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'bis (E)-4,6-dimethoxy-5-(p-tolyldiazenyl)pyrimidin-2-amine-co-adipic acid'
_chemical_formula_moiety         'C13 H15 N5 O2, 0.5(C6 H10 O4)'
_chemical_formula_sum            'C16 H20 N5 O4'
_chemical_formula_weight         346.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.1330(10)
_cell_length_b                   9.5050(12)
_cell_length_c                   11.7310(12)
_cell_angle_alpha                95.988(11)
_cell_angle_beta                 110.027(12)
_cell_angle_gamma                92.936(9)
_cell_volume                     843.69(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    120
_cell_measurement_theta_min      3.250
_cell_measurement_theta_max      20.822

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2001)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;

_diffrn_reflns_number            8542
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.673
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3831
_reflns_number_gt                2446
_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       'Collect (Nonius, 1999)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_structure_solution    
;
SIR97 (Altomare et al., 1999)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 2012) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012) and
OLEX2 (Dolomanov et al., 2009)
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0813P)²+0.1367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3831
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
O1 O 0.71293(18) 0.02100(15) 0.84143(14) 0.0494(4) Uani 1 1 d . . . . .
O2 O 0.42320(17) 0.21978(15) 0.48853(14) 0.0475(4) Uani 1 1 d . . . . .
N1 N 0.8711(2) 0.18694(19) 0.73468(17) 0.0477(4) Uani 1 1 d . . . . .
N2 N 0.7248(2) 0.20526(17) 0.66241(16) 0.0423(4) Uani 1 1 d . . . . .
N3 N 0.4162(2) -0.04002(16) 0.74072(16) 0.0398(4) Uani 1 1 d . . . . .
N4 N 0.1221(2) -0.0944(2) 0.6317(2) 0.0559(5) Uani 1 1 d . . . . .
H4A H 0.110(3) -0.133(3) 0.693(3) 0.067 Uiso 1 1 d . U . . .
H4B H 0.026(4) -0.079(3) 0.580(3) 0.067 Uiso 1 1 d . U . . .
N5 N 0.2679(2) 0.06228(17) 0.55724(15) 0.0390(4) Uani 1 1 d . . . . .
C1 C 1.4628(3) 0.5219(3) 0.7127(3) 0.0729(8) Uani 1 1 d . . . . .
H1B H 1.541463 0.556585 0.793957 0.109 Uiso 1 1 calc R U . . .
H1C H 1.425787 0.600683 0.668141 0.109 Uiso 1 1 calc R U . . .
H1A H 1.522081 0.461612 0.671684 0.109 Uiso 1 1 calc R U . . .
C2 C 1.3041(3) 0.4382(2) 0.7195(2) 0.0472(5) Uani 1 1 d . . . . .
C3 C 1.3213(3) 0.3317(2) 0.7932(2) 0.0522(5) Uani 1 1 d . . . . .
H3 H 1.433018 0.313205 0.842048 0.063 Uiso 1 1 calc R U . . .
C4 C 1.1766(3) 0.2522(2) 0.7959(2) 0.0477(5) Uani 1 1 d . . . . .
H4 H 1.191909 0.181191 0.846572 0.057 Uiso 1 1 calc R U . . .
C5 C 1.0109(2) 0.2764(2) 0.72516(18) 0.0400(4) Uani 1 1 d . . . . .
C6 C 0.9892(3) 0.3842(2) 0.6522(2) 0.0516(6) Uani 1 1 d . . . . .
H6 H 0.877010 0.402689 0.604318 0.062 Uiso 1 1 calc R U . . .
C7 C 1.1361(3) 0.4647(3) 0.6510(2) 0.0559(6) Uani 1 1 d . . . . .
H7 H 1.120626 0.538118 0.602782 0.067 Uiso 1 1 calc R U . . .
C8 C 0.5784(2) 0.12290(19) 0.66441(18) 0.0380(4) Uani 1 1 d . . . . .
C9 C 0.5662(2) 0.0319(2) 0.74904(19) 0.0377(4) Uani 1 1 d . . . . .
C10 C 0.2731(3) -0.0222(2) 0.64392(19) 0.0399(4) Uani 1 1 d . . . . .
C11 C 0.4187(2) 0.13327(19) 0.56984(18) 0.0377(4) Uani 1 1 d . . . . .
C12 C 0.2609(3) 0.2354(3) 0.3934(2) 0.0536(6) Uani 1 1 d . . . . .
H12A H 0.282950 0.295984 0.338647 0.080 Uiso 1 1 calc R U . . .
H12B H 0.181477 0.276762 0.428861 0.080 Uiso 1 1 calc R U . . .
H12C H 0.209740 0.143856 0.348956 0.080 Uiso 1 1 calc R U . . .
C13 C 0.7158(3) -0.0792(2) 0.9246(2) 0.0535(6) Uani 1 1 d . . . . .
H13A H 0.674943 -0.172121 0.879698 0.080 Uiso 1 1 calc R U . . .
H13B H 0.640583 -0.052784 0.969430 0.080 Uiso 1 1 calc R U . . .
H13C H 0.833692 -0.079897 0.980621 0.080 Uiso 1 1 calc R U . . .
O3 O 0.9271(2) 0.22239(19) 1.16639(18) 0.0678(5) Uani 1 1 d . . . . .
O4 O 0.6396(2) 0.23294(18) 1.08828(17) 0.0590(5) Uani 1 1 d . . . . .
H4C H 0.644(4) 0.175(3) 1.138(3) 0.071 Uiso 1 1 d . U . . .
C14 C 0.8044(3) 0.2709(2) 1.0984(2) 0.0423(5) Uani 1 1 d . . . . .
C15 C 0.8152(3) 0.3770(2) 1.0156(2) 0.0447(5) Uani 1 1 d . . . . .
H15B H 0.744208 0.453147 1.025112 0.054 Uiso 1 1 calc R U . . .
H15A H 0.765158 0.331576 0.931608 0.054 Uiso 1 1 calc R U . . .
C16 C 0.9992(2) 0.4403(2) 1.03812(19) 0.0402(4) Uani 1 1 d . . . . .
H16B H 1.067123 0.366552 1.018658 0.048 Uiso 1 1 calc R U . . .
H16A H 1.054945 0.476624 1.124144 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.326(2) . ?
O1 C13 1.428(2) . ?
O2 C11 1.331(2) . ?
O2 C12 1.433(2) . ?
N1 N2 1.235(2) . ?
N1 C5 1.427(2) . ?
N2 C8 1.400(2) . ?
N3 C9 1.336(2) . ?
N3 C10 1.352(3) . ?
N4 C10 1.331(2) . ?
N4 H4A 0.88(3) . ?
N4 H4B 0.84(3) . ?
N5 C11 1.323(2) . ?
N5 C10 1.351(2) . ?
C1 C2 1.511(3) . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1A 0.9600 . ?
C2 C7 1.379(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C6 C7 1.391(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C11 1.406(3) . ?
C8 C9 1.408(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O3 C14 1.193(3) . ?
O4 C14 1.332(2) . ?
O4 H4C 0.83(3) . ?
C14 C15 1.491(3) . ?
C15 C16 1.508(3) . ?
C15 H15B 0.9700 . ?
C15 H15A 0.9700 . ?
C16 C16 1.519(3) 2_767 ?
C16 H16B 0.9700 . ?
C16 H16A 0.9700 . ?

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
C9 O1 C13 120.19(15) . . ?
C11 O2 C12 117.69(14) . . ?
N2 N1 C5 113.63(16) . . ?
N1 N2 C8 118.23(16) . . ?
C9 N3 C10 116.05(15) . . ?
C10 N4 H4A 120.2(18) . . ?
C10 N4 H4B 121.8(18) . . ?
H4A N4 H4B 114(2) . . ?
C11 N5 C10 115.85(16) . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
H1B C1 H1A 109.5 . . ?
H1C C1 H1A 109.5 . . ?
C7 C2 C3 117.47(18) . . ?
C7 C2 C1 121.0(2) . . ?
C3 C2 C1 121.5(2) . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.27(18) . . ?
C4 C5 N1 115.86(18) . . ?
C6 C5 N1 124.87(18) . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 121.5(2) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N2 C8 C11 116.06(16) . . ?
N2 C8 C9 129.39(18) . . ?
C11 C8 C9 114.54(16) . . ?
O1 C9 N3 120.03(16) . . ?
O1 C9 C8 116.72(16) . . ?
N3 C9 C8 123.24(18) . . ?
N4 C10 N5 116.24(18) . . ?
N4 C10 N3 117.57(17) . . ?
N5 C10 N3 126.20(16) . . ?
N5 C11 O2 119.19(17) . . ?
N5 C11 C8 124.11(16) . . ?
O2 C11 C8 116.69(15) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 O4 H4C 106.9(19) . . ?
O3 C14 O4 122.26(18) . . ?
O3 C14 C15 125.18(18) . . ?
O4 C14 C15 112.56(18) . . ?
C14 C15 C16 114.28(17) . . ?
C14 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
H15B C15 H15A 107.6 . . ?
C15 C16 C16 112.0(2) . 2_767 ?
C15 C16 H16B 109.2 . . ?
C16 C16 H16B 109.2 2_767 . ?
C15 C16 H16A 109.2 . . ?
C16 C16 H16A 109.2 2_767 . ?
H16B C16 H16A 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C8 -179.86(17) . . . . ?
C7 C2 C3 C4 1.7(4) . . . . ?
C1 C2 C3 C4 -177.7(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C5 N1 179.5(2) . . . . ?
N2 N1 C5 C4 -174.79(19) . . . . ?
N2 N1 C5 C6 6.2(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
N1 C5 C6 C7 179.8(2) . . . . ?
C3 C2 C7 C6 -2.3(4) . . . . ?
C1 C2 C7 C6 177.1(2) . . . . ?
C5 C6 C7 C2 1.1(4) . . . . ?
N1 N2 C8 C11 -171.53(18) . . . . ?
N1 N2 C8 C9 9.6(3) . . . . ?
C13 O1 C9 N3 7.0(3) . . . . ?
C13 O1 C9 C8 -174.00(19) . . . . ?
C10 N3 C9 O1 179.74(18) . . . . ?
C10 N3 C9 C8 0.8(3) . . . . ?
N2 C8 C9 O1 0.2(3) . . . . ?
C11 C8 C9 O1 -178.61(17) . . . . ?
N2 C8 C9 N3 179.25(19) . . . . ?
C11 C8 C9 N3 0.4(3) . . . . ?
C11 N5 C10 N4 -179.77(19) . . . . ?
C11 N5 C10 N3 0.1(3) . . . . ?
C9 N3 C10 N4 178.79(19) . . . . ?
C9 N3 C10 N5 -1.1(3) . . . . ?
C10 N5 C11 O2 -179.31(17) . . . . ?
C10 N5 C11 C8 1.2(3) . . . . ?
C12 O2 C11 N5 2.4(3) . . . . ?
C12 O2 C11 C8 -178.15(19) . . . . ?
N2 C8 C11 N5 179.51(18) . . . . ?
C9 C8 C11 N5 -1.5(3) . . . . ?
N2 C8 C11 O2 0.1(3) . . . . ?
C9 C8 C11 O2 179.07(17) . . . . ?
O3 C14 C15 C16 -9.9(3) . . . . ?
O4 C14 C15 C16 170.74(19) . . . . ?
C14 C15 C16 C16 -173.3(2) . . . 2_767 ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/heptane'
####################################################################### 
# 
# 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_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2073784'
loop_
_audit_author_name
_audit_author_address
'Roberto Centore'
;University of Naples Federico II
Italy
;
_audit_update_record             
;
2021-03-28 deposited with the CCDC.	2021-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'bis (E)-4,6-dimethoxy-5-(p-tolyldiazenyl)pyrimidin-2-amine-co-adipic acid'
_chemical_formula_moiety         'C13 H15 N5 O2, 0.5(C6 H10 O4)'
_chemical_formula_sum            'C16 H20 N5 O4'
_chemical_formula_weight         346.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.095(2)
_cell_length_b                   9.351(2)
_cell_length_c                   11.6500(14)
_cell_angle_alpha                96.706(14)
_cell_angle_beta                 110.152(16)
_cell_angle_gamma                92.33(2)
_cell_volume                     819.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    210
_cell_measurement_theta_min      3.495
_cell_measurement_theta_max      23.264

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2001)
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;

_diffrn_reflns_number            10072
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.686
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3722
_reflns_number_gt                2809
_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       'Collect (Nonius, 1999)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_structure_solution    
;
SIR97 (Altomare et al., 1999)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 2012) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012) and
OLEX2 (Dolomanov et al., 2009)
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0734P)²+0.1315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3722
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
O1 O 0.71483(15) 0.02246(12) 0.34231(10) 0.0265(3) Uani 1 1 d . . . . .
O2 O 0.42051(15) 0.22106(12) -0.01382(10) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.87314(18) 0.18860(15) 0.23550(12) 0.0252(3) Uani 1 1 d . . . . .
N2 N 0.72375(18) 0.20708(14) 0.16103(12) 0.0225(3) Uani 1 1 d . . . . .
N3 N 0.41755(18) -0.03950(14) 0.24135(12) 0.0226(3) Uani 1 1 d . . . . .
N4 N 0.26645(18) 0.06269(14) 0.05608(12) 0.0221(3) Uani 1 1 d . . . . .
N5 N 0.1225(2) -0.09541(17) 0.13173(15) 0.0317(4) Uani 1 1 d . . . . .
H5A H 0.115(3) -0.134(2) 0.193(2) 0.038 Uiso 1 1 d . U . . .
H5B H 0.033(3) -0.078(2) 0.079(2) 0.038 Uiso 1 1 d . U . . .
C1 C 1.4624(3) 0.5257(2) 0.21154(19) 0.0383(4) Uani 1 1 d . . . . .
H1A H 1.517220 0.464463 0.163143 0.057 Uiso 1 1 calc R U . . .
H1B H 1.548323 0.556142 0.294830 0.057 Uiso 1 1 calc R U . . .
H1C H 1.424299 0.611206 0.171402 0.057 Uiso 1 1 calc R U . . .
C2 C 1.3054(2) 0.44217(18) 0.21955(15) 0.0265(4) Uani 1 1 d . . . . .
C3 C 1.3259(2) 0.33405(18) 0.29431(15) 0.0278(4) Uani 1 1 d . . . . .
H3 H 1.441164 0.315239 0.344154 0.033 Uiso 1 1 calc R U . . .
C4 C 1.1803(2) 0.25320(18) 0.29713(14) 0.0254(3) Uani 1 1 d . . . . .
H4 H 1.196782 0.179822 0.348999 0.030 Uiso 1 1 calc R U . . .
C5 C 1.0114(2) 0.27832(16) 0.22519(14) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.9884(2) 0.38856(18) 0.15189(15) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.872957 0.408484 0.103295 0.033 Uiso 1 1 calc R U . . .
C7 C 1.1348(2) 0.46895(18) 0.15031(15) 0.0292(4) Uani 1 1 d . . . . .
H7 H 1.118132 0.544453 0.100530 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5779(2) 0.12456(16) 0.16339(14) 0.0214(3) Uani 1 1 d . . . . .
C9 C 0.5667(2) 0.03267(16) 0.24908(14) 0.0213(3) Uani 1 1 d . . . . .
C10 C 0.2728(2) -0.02195(16) 0.14350(14) 0.0223(3) Uani 1 1 d . . . . .
C11 C 0.4166(2) 0.13394(16) 0.06813(14) 0.0212(3) Uani 1 1 d . . . . .
C12 C 0.2560(2) 0.23584(19) -0.10964(16) 0.0293(4) Uani 1 1 d . . . . .
H12A H 0.204802 0.140482 -0.155775 0.044 Uiso 1 1 calc R U . . .
H12B H 0.276954 0.298715 -0.165799 0.044 Uiso 1 1 calc R U . . .
H12C H 0.174208 0.278405 -0.072698 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7171(2) -0.07896(18) 0.42617(15) 0.0284(4) Uani 1 1 d . . . . .
H13A H 0.639273 -0.050673 0.471737 0.043 Uiso 1 1 calc R U . . .
H13B H 0.837861 -0.079732 0.484439 0.043 Uiso 1 1 calc R U . . .
H13C H 0.675880 -0.175718 0.379618 0.043 Uiso 1 1 calc R U . . .
O5 O 0.92520(17) 0.21670(15) 0.66311(12) 0.0373(3) Uani 1 1 d . . . . .
O6 O 0.63516(16) 0.23381(14) 0.58719(12) 0.0318(3) Uani 1 1 d . . . . .
H6A H 0.634(3) 0.178(2) 0.635(2) 0.038 Uiso 1 1 d . U . . .
C17 C 0.9988(2) 0.43853(16) 0.53709(14) 0.0228(3) Uani 1 1 d . . . . .
H17A H 1.066076 0.360813 0.514468 0.027 Uiso 1 1 calc R U . . .
H17B H 1.057840 0.474198 0.626122 0.027 Uiso 1 1 calc R U . . .
C18 C 0.8127(2) 0.37753(17) 0.51413(15) 0.0243(3) Uani 1 1 d . . . . .
H18A H 0.741934 0.458107 0.525879 0.029 Uiso 1 1 calc R U . . .
H18B H 0.759648 0.331535 0.427126 0.029 Uiso 1 1 calc R U . . .
C19 C 0.8012(2) 0.26868(17) 0.59652(14) 0.0235(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
O1 C9 1.3275(19) . ?
O1 C13 1.4351(17) . ?
O2 C11 1.3328(17) . ?
O2 C12 1.437(2) . ?
N1 N2 1.2546(19) . ?
N1 C5 1.418(2) . ?
N2 C8 1.394(2) . ?
N3 C9 1.329(2) . ?
N3 C10 1.356(2) . ?
N4 C11 1.318(2) . ?
N4 C10 1.3498(19) . ?
N5 C10 1.328(2) . ?
N5 H5A 0.85(2) . ?
N5 H5B 0.81(2) . ?
C1 C2 1.501(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.389(2) . ?
C2 C7 1.389(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C11 1.406(2) . ?
C8 C9 1.414(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O5 C19 1.199(2) . ?
O6 C19 1.334(2) . ?
O6 H6A 0.80(2) . ?
C17 C18 1.511(2) . ?
C17 C17 1.520(3) 2_766 ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.499(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C9 O1 C13 119.60(13) . . ?
C11 O2 C12 117.23(12) . . ?
N2 N1 C5 113.13(12) . . ?
N1 N2 C8 117.99(13) . . ?
C9 N3 C10 115.81(12) . . ?
C11 N4 C10 116.00(14) . . ?
C10 N5 H5A 119.1(15) . . ?
C10 N5 H5B 117.9(16) . . ?
H5A N5 H5B 119(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.95(15) . . ?
C3 C2 C1 121.21(16) . . ?
C7 C2 C1 120.83(16) . . ?
C4 C3 C2 120.83(15) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.63(15) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.25(14) . . ?
C4 C5 N1 115.53(13) . . ?
C6 C5 N1 125.20(14) . . ?
C7 C6 C5 119.55(15) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 121.76(15) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
N2 C8 C11 116.25(13) . . ?
N2 C8 C9 129.44(14) . . ?
C11 C8 C9 114.31(14) . . ?
O1 C9 N3 119.89(13) . . ?
O1 C9 C8 116.63(14) . . ?
N3 C9 C8 123.46(14) . . ?
N5 C10 N4 116.58(15) . . ?
N5 C10 N3 117.17(14) . . ?
N4 C10 N3 126.25(14) . . ?
N4 C11 O2 119.51(14) . . ?
N4 C11 C8 124.16(13) . . ?
O2 C11 C8 116.34(14) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 O6 H6A 109.6(16) . . ?
C18 C17 C17 111.73(17) . 2_766 ?
C18 C17 H17A 109.3 . . ?
C17 C17 H17A 109.3 2_766 . ?
C18 C17 H17B 109.3 . . ?
C17 C17 H17B 109.3 2_766 . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 114.00(14) . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.6 . . ?
O5 C19 O6 122.87(14) . . ?
O5 C19 C18 124.78(15) . . ?
O6 C19 C18 112.35(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C8 -179.81(13) . . . . ?
C7 C2 C3 C4 1.6(2) . . . . ?
C1 C2 C3 C4 -177.21(16) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C3 C4 C5 N1 179.79(14) . . . . ?
N2 N1 C5 C4 -174.33(14) . . . . ?
N2 N1 C5 C6 7.2(2) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
N1 C5 C6 C7 179.76(15) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C3 C2 C7 C6 -1.9(2) . . . . ?
C1 C2 C7 C6 176.91(16) . . . . ?
N1 N2 C8 C11 -171.73(14) . . . . ?
N1 N2 C8 C9 9.1(2) . . . . ?
C13 O1 C9 N3 7.1(2) . . . . ?
C13 O1 C9 C8 -174.18(14) . . . . ?
C10 N3 C9 O1 179.63(14) . . . . ?
C10 N3 C9 C8 1.0(2) . . . . ?
N2 C8 C9 O1 0.6(2) . . . . ?
C11 C8 C9 O1 -178.65(13) . . . . ?
N2 C8 C9 N3 179.29(14) . . . . ?
C11 C8 C9 N3 0.1(2) . . . . ?
C11 N4 C10 N5 -179.39(14) . . . . ?
C11 N4 C10 N3 0.2(2) . . . . ?
C9 N3 C10 N5 178.46(15) . . . . ?
C9 N3 C10 N4 -1.2(2) . . . . ?
C10 N4 C11 O2 -179.23(13) . . . . ?
C10 N4 C11 C8 0.9(2) . . . . ?
C12 O2 C11 N4 2.1(2) . . . . ?
C12 O2 C11 C8 -178.04(14) . . . . ?
N2 C8 C11 N4 179.58(14) . . . . ?
C9 C8 C11 N4 -1.1(2) . . . . ?
N2 C8 C11 O2 -0.3(2) . . . . ?
C9 C8 C11 O2 179.08(13) . . . . ?
C17 C17 C18 C19 -172.76(16) 2_766 . . . ?
C17 C18 C19 O5 -10.2(2) . . . . ?
C17 C18 C19 O6 170.34(14) . . . . ?

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/heptane'
####################################################################### 
# 
# 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_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2073782'
loop_
_audit_author_name
_audit_author_address
'Roberto Centore'
;University of Naples Federico II
Italy
;
_audit_update_record             
;
2021-03-28 deposited with the CCDC.	2021-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
(E)-4,6-dimethoxy-5-(p-tolyldiazenyl)pyrimidin-2-amine
;
_chemical_name_common            'Polymorph II'
_chemical_formula_moiety         'C13 H15 N5 O2'
_chemical_formula_sum            'C13 H15 N5 O2'
_chemical_formula_weight         273.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.632(3)
_cell_length_b                   20.892(8)
_cell_length_c                   10.929(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.57(2)
_cell_angle_gamma                90
_cell_volume                     1435.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    135
_cell_measurement_theta_min      3.530
_cell_measurement_theta_max      21.842

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2001)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;

_diffrn_reflns_number            8904
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.769
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3199
_reflns_number_gt                2111
_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       'Collect (Nonius, 1999)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_structure_solution    
;
SIR97 (Altomare et al., 1999)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 2012) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012) and
OLEX2 (Dolomanov et al., 2009)
;

_refine_special_details          
;
The structure shows positional disorder of the 4-methylphenylazo 
group, which is typical of azocompounds ("pedal motion"). The two split 
positions have different occupation factors, with the minor component 
having sof of 0.136(4). For this reason, the atoms of the minor 
component were refined isotropically.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.2217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3199
_refine_ls_number_parameters     227
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_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 0.1220(7) 0.58732(17) 0.0989(4) 0.1046(13) Uani 0.864(4) 1 d D . P A 1
H1A H -0.015990 0.586031 0.109743 0.157 Uiso 0.864(4) 1 calc R U P A 1
H1B H 0.107531 0.582332 0.009209 0.157 Uiso 0.864(4) 1 calc R U P A 1
H1C H 0.188523 0.627667 0.129240 0.157 Uiso 0.864(4) 1 calc R U P A 1
C2 C 0.2584(10) 0.5333(3) 0.1760(7) 0.066(2) Uani 0.864(4) 1 d D . P A 1
C3 C 0.2205(7) 0.50772(15) 0.2812(4) 0.0777(10) Uani 0.864(4) 1 d D . P A 1
H3 H 0.107666 0.523086 0.305978 0.093 Uiso 0.864(4) 1 calc R U P A 1
C4 C 0.3473(5) 0.45912(13) 0.3519(3) 0.0680(7) Uani 0.864(4) 1 d D . P A 1
H4 H 0.316801 0.441479 0.422167 0.082 Uiso 0.864(4) 1 calc R U P A 1
C5 C 0.5200(4) 0.43663(9) 0.3184(2) 0.0453(6) Uani 0.864(4) 1 d D . P A 1
C6 C 0.5630(4) 0.46366(12) 0.2144(3) 0.0599(7) Uani 0.864(4) 1 d D . P A 1
H6 H 0.680235 0.450262 0.191922 0.072 Uiso 0.864(4) 1 calc R U P A 1
C7 C 0.4297(7) 0.51107(18) 0.1435(4) 0.0707(12) Uani 0.864(4) 1 d D . P A 1
H7 H 0.457133 0.528286 0.071880 0.085 Uiso 0.864(4) 1 calc R U P A 1
N1 N 0.6662(3) 0.38983(8) 0.39196(18) 0.0478(5) Uani 0.864(4) 1 d D . P A 1
N2 N 0.5809(4) 0.35140(8) 0.44999(17) 0.0474(5) Uani 0.864(4) 1 d D . P A 1
C8 C 0.7194(3) 0.30889(7) 0.53606(15) 0.0453(4) Uani 1 1 d . . . . .
C9 C 0.6236(2) 0.25445(8) 0.56939(16) 0.0457(4) Uani 1 1 d . . . . .
C10 C 0.9291(2) 0.22469(8) 0.71982(15) 0.0452(4) Uani 1 1 d . . . . .
C11 C 0.9368(3) 0.31508(8) 0.60719(15) 0.0444(4) Uani 1 1 d . . . . .
C12 C 0.3164(3) 0.18988(9) 0.5374(2) 0.0690(6) Uani 1 1 d . . . . .
H12A H 0.167823 0.190023 0.488411 0.104 Uiso 1 1 calc R U . . .
H12B H 0.332841 0.190825 0.627835 0.104 Uiso 1 1 calc R U . . .
H12C H 0.381484 0.151826 0.517928 0.104 Uiso 1 1 calc R U . . .
C13 C 1.2580(3) 0.37456(10) 0.6649(2) 0.0695(6) Uani 1 1 d . . . . .
H13A H 1.312396 0.414005 0.642968 0.104 Uiso 1 1 calc R U . . .
H13B H 1.342343 0.339526 0.651565 0.104 Uiso 1 1 calc R U . . .
H13C H 1.264098 0.375688 0.753793 0.104 Uiso 1 1 calc R U . . .
N3 N 0.7220(2) 0.21218(6) 0.65705(13) 0.0481(4) Uani 1 1 d . . . . .
N4 N 1.0409(2) 0.27471(7) 0.69808(13) 0.0476(4) Uani 1 1 d . . . . .
N5 N 1.0310(3) 0.18309(8) 0.81128(16) 0.0618(5) Uani 1 1 d . . . . .
H5A H 1.169(4) 0.1893(10) 0.855(2) 0.074 Uiso 1 1 d . U . . .
H5B H 0.964(3) 0.1514(11) 0.835(2) 0.074 Uiso 1 1 d . U . . .
O1 O 0.41701(18) 0.24526(6) 0.50421(13) 0.0610(4) Uani 1 1 d . . . . .
O2 O 1.04132(18) 0.36627(6) 0.58452(11) 0.0561(4) Uani 1 1 d . . . . .
C1B C 0.205(5) 0.5906(13) 0.071(3) 0.109(11) Uiso 0.136(4) 1 d D . P A 2
H1B1 H 0.309979 0.596961 0.029344 0.163 Uiso 0.136(4) 1 calc R U P A 2
H1B2 H 0.070171 0.581054 0.007944 0.163 Uiso 0.136(4) 1 calc R U P A 2
H1B3 H 0.191857 0.628753 0.117263 0.163 Uiso 0.136(4) 1 calc R U P A 2
C2B C 0.271(8) 0.535(3) 0.166(6) 0.087(19) Uiso 0.136(4) 1 d D . P A 2
C3B C 0.161(5) 0.5121(14) 0.243(3) 0.112(14) Uiso 0.136(4) 1 d D . P A 2
H3B H 0.032720 0.532160 0.236624 0.134 Uiso 0.136(4) 1 calc R U P A 2
C4B C 0.222(3) 0.4624(9) 0.3281(18) 0.076(6) Uiso 0.136(4) 1 d D . P A 2
H4B H 0.143591 0.450867 0.381665 0.092 Uiso 0.136(4) 1 calc R U P A 2
C5B C 0.408(3) 0.4298(6) 0.3313(12) 0.045(4) Uiso 0.136(4) 1 d D . P A 2
C6B C 0.515(3) 0.4474(7) 0.2494(18) 0.045(4) Uiso 0.136(4) 1 d D . P A 2
H6B H 0.628162 0.422470 0.243561 0.054 Uiso 0.136(4) 1 calc R U P A 2
C7B C 0.459(4) 0.5028(12) 0.174(2) 0.065(9) Uiso 0.136(4) 1 d D . P A 2
H7B H 0.545918 0.518131 0.128617 0.078 Uiso 0.136(4) 1 calc R U P A 2
N1B N 0.4702(17) 0.3754(5) 0.4169(10) 0.049(3) Uiso 0.136(4) 1 d D . P A 2
N2B N 0.666(2) 0.3652(7) 0.4535(15) 0.050(4) Uiso 0.136(4) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.521(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.363(5) . ?
C2 C7 1.375(5) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 N1 1.430(3) . ?
C6 C7 1.388(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
N1 N2 1.263(3) . ?
N2 C8 1.403(2) . ?
C8 C9 1.406(2) . ?
C8 C11 1.409(2) . ?
C8 N2B 1.455(17) . ?
C9 N3 1.314(2) . ?
C9 O1 1.341(2) . ?
C10 N5 1.335(2) . ?
C10 N4 1.346(2) . ?
C10 N3 1.351(2) . ?
C11 N4 1.318(2) . ?
C11 O2 1.340(2) . ?
C12 O1 1.438(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O2 1.436(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N5 H5A 0.90(2) . ?
N5 H5B 0.88(2) . ?
C1B C2B 1.532(17) . ?
C1B H1B1 0.9600 . ?
C1B H1B2 0.9600 . ?
C1B H1B3 0.9600 . ?
C2B C3B 1.359(17) . ?
C2B C7B 1.388(17) . ?
C3B C4B 1.367(17) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.398(16) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.363(15) . ?
C5B N1B 1.445(13) . ?
C6B C7B 1.401(16) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
N1B N2B 1.251(13) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.4(3) . . ?
C3 C2 C1 121.4(4) . . ?
C7 C2 C1 120.2(4) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 N1 117.6(2) . . ?
C4 C5 N1 123.4(3) . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 121.9(3) . . ?
C2 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
N2 N1 C5 112.6(2) . . ?
N1 N2 C8 115.9(2) . . ?
N2 C8 C9 115.61(16) . . ?
N2 C8 C11 130.42(17) . . ?
C9 C8 C11 113.50(14) . . ?
C9 C8 N2B 140.7(5) . . ?
C11 C8 N2B 105.8(5) . . ?
N3 C9 O1 118.51(15) . . ?
N3 C9 C8 124.90(15) . . ?
O1 C9 C8 116.59(14) . . ?
N5 C10 N4 117.51(15) . . ?
N5 C10 N3 116.40(15) . . ?
N4 C10 N3 126.09(14) . . ?
N4 C11 O2 118.18(14) . . ?
N4 C11 C8 123.73(15) . . ?
O2 C11 C8 118.03(14) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 N3 C10 115.40(14) . . ?
C11 N4 C10 116.36(14) . . ?
C10 N5 H5A 119.6(14) . . ?
C10 N5 H5B 121.9(15) . . ?
H5A N5 H5B 118(2) . . ?
C9 O1 C12 117.29(13) . . ?
C11 O2 C13 117.32(14) . . ?
C2B C1B H1B1 109.5 . . ?
C2B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
C2B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?
C3B C2B C7B 116.4(18) . . ?
C3B C2B C1B 126(2) . . ?
C7B C2B C1B 117.7(19) . . ?
C2B C3B C4B 126(2) . . ?
C2B C3B H3B 117.2 . . ?
C4B C3B H3B 117.2 . . ?
C3B C4B C5B 117.1(16) . . ?
C3B C4B H4B 121.5 . . ?
C5B C4B H4B 121.5 . . ?
C6B C5B C4B 119.6(12) . . ?
C6B C5B N1B 122.3(15) . . ?
C4B C5B N1B 117.9(14) . . ?
C5B C6B C7B 120.7(14) . . ?
C5B C6B H6B 119.6 . . ?
C7B C6B H6B 119.6 . . ?
C2B C7B C6B 119.9(17) . . ?
C2B C7B H7B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
N2B N1B C5B 113.4(12) . . ?
N1B N2B C8 111.1(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
C7 C2 C3 C4 -1.8(10) . . . . ?
C1 C2 C3 C4 -179.1(5) . . . . ?
C2 C3 C4 C5 1.6(7) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C3 C4 C5 N1 175.5(3) . . . . ?
C4 C5 C6 C7 -2.0(4) . . . . ?
N1 C5 C6 C7 -177.5(3) . . . . ?
C3 C2 C7 C6 0.1(10) . . . . ?
C1 C2 C7 C6 177.4(5) . . . . ?
C5 C6 C7 C2 1.8(7) . . . . ?
C6 C5 N1 N2 -154.75(19) . . . . ?
C4 C5 N1 N2 30.0(3) . . . . ?
C5 N1 N2 C8 -172.78(16) . . . . ?
N1 N2 C8 C9 -160.99(16) . . . . ?
N1 N2 C8 C11 27.4(3) . . . . ?
N2 C8 C9 N3 -173.43(16) . . . . ?
C11 C8 C9 N3 -0.4(3) . . . . ?
N2B C8 C9 N3 -176.5(9) . . . . ?
N2 C8 C9 O1 7.7(2) . . . . ?
C11 C8 C9 O1 -179.27(14) . . . . ?
N2B C8 C9 O1 4.7(10) . . . . ?
N2 C8 C11 N4 170.49(18) . . . . ?
C9 C8 C11 N4 -1.2(2) . . . . ?
N2B C8 C11 N4 176.2(6) . . . . ?
N2 C8 C11 O2 -6.8(3) . . . . ?
C9 C8 C11 O2 -178.52(14) . . . . ?
N2B C8 C11 O2 -1.1(6) . . . . ?
O1 C9 N3 C10 -179.40(15) . . . . ?
C8 C9 N3 C10 1.8(3) . . . . ?
N5 C10 N3 C9 178.59(16) . . . . ?
N4 C10 N3 C9 -1.8(3) . . . . ?
O2 C11 N4 C10 178.59(14) . . . . ?
C8 C11 N4 C10 1.3(2) . . . . ?
N5 C10 N4 C11 179.93(16) . . . . ?
N3 C10 N4 C11 0.3(3) . . . . ?
N3 C9 O1 C12 1.2(2) . . . . ?
C8 C9 O1 C12 -179.84(16) . . . . ?
N4 C11 O2 C13 -2.3(2) . . . . ?
C8 C11 O2 C13 175.15(16) . . . . ?
C7B C2B C3B C4B 2(9) . . . . ?
C1B C2B C3B C4B -180(5) . . . . ?
C2B C3B C4B C5B -4(6) . . . . ?
C3B C4B C5B C6B -1(3) . . . . ?
C3B C4B C5B N1B -177(2) . . . . ?
C4B C5B C6B C7B 8(3) . . . . ?
N1B C5B C6B C7B -175.8(19) . . . . ?
C3B C2B C7B C6B 5(9) . . . . ?
C1B C2B C7B C6B -174(4) . . . . ?
C5B C6B C7B C2B -10(5) . . . . ?
C6B C5B N1B N2B 30.9(19) . . . . ?
C4B C5B N1B N2B -153.0(15) . . . . ?
C5B N1B N2B C8 -178.2(10) . . . . ?
C9 C8 N2B N1B 17.0(18) . . . . ?
C11 C8 N2B N1B -159.2(10) . . . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol/water'
