# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

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

data_PTD
_database_code_depnum_ccdc_archive 'CCDC 1984000'
loop_
_audit_author_name
_audit_author_address
'Javier Marti-Rujas'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2020-02-14 deposited with the CCDC.	2020-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N7 O2'
_chemical_formula_weight         329.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   19.985(3)
_cell_length_b                   7.6989(10)
_cell_length_c                   21.093(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3245.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1021
_cell_measurement_theta_min      4.19
_cell_measurement_theta_max      64.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.784
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9258
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.192
_diffrn_reflns_theta_max         66.072
_diffrn_reflns_theta_full        66.072
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2746
_reflns_number_gt                2372
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+0.3901P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2746
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
N1 N 0.19701(6) 0.23353(16) 0.13298(6) 0.0460(3) Uani 1 1 d . . . . .
N4 N 0.41220(6) 0.13105(15) 0.18459(5) 0.0433(3) Uani 1 1 d . . . . .
N7 N 0.61125(6) 0.08964(17) 0.12115(6) 0.0500(3) Uani 1 1 d . . . . .
N5 N 0.58866(7) 0.06094(19) 0.21976(6) 0.0594(4) Uani 1 1 d . . . . .
N3 N 0.30088(6) 0.22840(18) 0.11029(6) 0.0514(3) Uani 1 1 d . . . . .
N2 N 0.24157(6) 0.26265(18) 0.08671(6) 0.0551(3) Uani 1 1 d . . . . .
O1 O 0.02302(6) 0.2564(2) 0.02052(6) 0.0825(5) Uani 1 1 d . . . . .
H1 H -0.015657 0.277319 0.010008 0.124 Uiso 1 1 calc R U . . .
C1 C 0.02308(8) 0.1348(3) 0.07072(8) 0.0621(4) Uani 1 1 d . . . . .
H1A H 0.001332 0.028279 0.057364 0.075 Uiso 1 1 calc R U . . .
H1B H -0.001204 0.181263 0.106747 0.075 Uiso 1 1 calc R U . . .
C2 C 0.09482(7) 0.0982(2) 0.08914(8) 0.0550(4) Uani 1 1 d . . . . .
H2A H 0.096287 0.000100 0.117959 0.066 Uiso 1 1 calc R U . . .
H2B H 0.120420 0.068323 0.051618 0.066 Uiso 1 1 calc R U . . .
C3 C 0.12545(7) 0.25472(19) 0.12058(7) 0.0502(4) Uani 1 1 d . . . . .
H3A H 0.118877 0.355371 0.093632 0.060 Uiso 1 1 calc R U . . .
H3B H 0.102533 0.276317 0.160346 0.060 Uiso 1 1 calc R U . . .
C4 C 0.22758(7) 0.1803(2) 0.18586(7) 0.0471(3) Uani 1 1 d . . . . .
H4 H 0.207664 0.151062 0.224253 0.057 Uiso 1 1 calc R U . . .
C5 C 0.29432(7) 0.17796(18) 0.17161(6) 0.0429(3) Uani 1 1 d . . . . .
C6 C 0.35146(7) 0.12613(17) 0.21133(6) 0.0429(3) Uani 1 1 d . . . . .
C10 C 0.46440(7) 0.07450(17) 0.21929(7) 0.0438(3) Uani 1 1 d . . . . .
C11 C 0.52983(7) 0.07627(18) 0.18762(7) 0.0460(3) Uani 1 1 d . . . . .
C12 C 0.54447(7) 0.0942(2) 0.12469(7) 0.0487(4) Uani 1 1 d . . . . .
H12 H 0.514368 0.106899 0.091389 0.058 Uiso 1 1 calc R U . . .
C13 C 0.65422(8) 0.1043(2) 0.06504(8) 0.0584(4) Uani 1 1 d . . . . .
H13A H 0.684395 0.201810 0.070525 0.070 Uiso 1 1 calc R U . . .
H13B H 0.626587 0.127560 0.028199 0.070 Uiso 1 1 calc R U . . .
C14 C 0.69478(8) -0.0584(2) 0.05333(8) 0.0626(4) Uani 1 1 d . . . . .
H14A H 0.724059 -0.039313 0.017319 0.075 Uiso 1 1 calc R U . . .
H14B H 0.722664 -0.080971 0.090051 0.075 Uiso 1 1 calc R U . . .
C15 C 0.65182(9) -0.2151(2) 0.04063(9) 0.0654(5) Uani 1 1 d . . . . .
H15A H 0.680471 -0.313754 0.031652 0.079 Uiso 1 1 calc R U . . .
H15B H 0.626170 -0.241903 0.078425 0.079 Uiso 1 1 calc R U . . .
N6 N 0.63839(7) 0.0695(2) 0.17919(7) 0.0619(4) Uani 1 1 d . . . . .
C7 C 0.34101(8) 0.0691(2) 0.27339(7) 0.0524(4) Uani 1 1 d . . . . .
H7 H 0.298328 0.069343 0.290971 0.063 Uiso 1 1 calc R U . . .
C8 C 0.39508(9) 0.0124(2) 0.30797(7) 0.0573(4) Uani 1 1 d . . . . .
H8 H 0.389347 -0.026429 0.349367 0.069 Uiso 1 1 calc R U . . .
C9 C 0.45771(8) 0.0136(2) 0.28095(7) 0.0529(4) Uani 1 1 d . . . . .
H9 H 0.494769 -0.025507 0.303466 0.064 Uiso 1 1 calc R U . . .
O2 O 0.60726(6) -0.19055(17) -0.01083(6) 0.0668(3) Uani 1 1 d D . . . .
H2C H 0.6293(11) -0.208(3) -0.0444(9) 0.103(8) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.3362(19) . ?
N1 N2 1.3401(17) . ?
N1 C3 1.4629(18) . ?
N4 C6 1.3391(18) . ?
N4 C10 1.3465(18) . ?
N7 C12 1.3371(18) . ?
N7 N6 1.3480(18) . ?
N7 C13 1.4665(19) . ?
N5 N6 1.313(2) . ?
N5 C11 1.3622(18) . ?
N3 N2 1.3122(17) . ?
N3 C5 1.3570(18) . ?
O1 C1 1.414(2) . ?
C1 C2 1.512(2) . ?
C2 C3 1.506(2) . ?
C4 C5 1.367(2) . ?
C5 C6 1.4714(19) . ?
C6 C7 1.396(2) . ?
C10 C9 1.389(2) . ?
C10 C11 1.468(2) . ?
C11 C12 1.366(2) . ?
C13 C14 1.512(2) . ?
C14 C15 1.505(3) . ?
C15 O2 1.417(2) . ?
C7 C8 1.375(2) . ?
C8 C9 1.375(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 N2 110.82(12) . . ?
C4 N1 C3 129.07(13) . . ?
N2 N1 C3 120.05(12) . . ?
C6 N4 C10 117.66(12) . . ?
C12 N7 N6 110.72(13) . . ?
C12 N7 C13 128.87(13) . . ?
N6 N7 C13 120.41(13) . . ?
N6 N5 C11 108.94(13) . . ?
N2 N3 C5 109.36(11) . . ?
N3 N2 N1 106.89(11) . . ?
O1 C1 C2 108.47(13) . . ?
C3 C2 C1 110.46(13) . . ?
N1 C3 C2 112.77(12) . . ?
N1 C4 C5 105.46(12) . . ?
N3 C5 C4 107.45(12) . . ?
N3 C5 C6 123.05(12) . . ?
C4 C5 C6 129.46(13) . . ?
N4 C6 C7 122.64(13) . . ?
N4 C6 C5 117.13(12) . . ?
C7 C6 C5 120.20(13) . . ?
N4 C10 C9 122.91(13) . . ?
N4 C10 C11 116.08(13) . . ?
C9 C10 C11 120.99(13) . . ?
N5 C11 C12 107.90(13) . . ?
N5 C11 C10 122.78(13) . . ?
C12 C11 C10 129.31(13) . . ?
N7 C12 C11 105.39(12) . . ?
N7 C13 C14 112.47(14) . . ?
C15 C14 C13 112.78(14) . . ?
O2 C15 C14 112.84(15) . . ?
N5 N6 N7 107.04(12) . . ?
C8 C7 C6 118.66(14) . . ?
C7 C8 C9 119.56(14) . . ?
C8 C9 C10 118.56(14) . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.055

