# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_dc
_database_code_depnum_ccdc_archive 'CCDC 1580078'
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Cl N6 O2'
_chemical_formula_sum            'C12 H9 Cl N6 O2'
_chemical_formula_weight         304.70

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7035(13)
_cell_length_b                   11.4502(13)
_cell_length_c                   14.6009(16)
_cell_angle_alpha                83.388(9)
_cell_angle_beta                 80.279(11)
_cell_angle_gamma                82.689(11)
_cell_volume                     1253.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3638
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.37

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_min  0.75420
_exptl_absorpt_correction_T_max  1.19578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13682
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0738
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4875
_reflns_number_gt                2465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4875
_refine_ls_number_parameters     415
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.03807(14) 0.66599(9) 0.23935(6) 0.0685(3) Uani 1 1 d . . .
N1 N 0.1816(3) 0.6003(2) 0.62502(16) 0.0364(6) Uani 1 1 d . . .
C1 C 0.1653(5) 0.5809(3) 1.0177(3) 0.0543(10) Uani 1 1 d . . .
O1 O -0.1366(4) 0.8671(2) 0.94893(18) 0.0745(8) Uani 1 1 d . . .
O2 O -0.0752(3) 0.8168(2) 0.81020(16) 0.0604(7) Uani 1 1 d . . .
N2 N 0.3441(4) 0.5529(3) 0.64141(18) 0.0555(8) Uani 1 1 d . . .
C2 C 0.0431(4) 0.6971(3) 0.9233(2) 0.0404(8) Uani 1 1 d . . .
C3 C 0.1472(4) 0.6165(3) 0.8695(2) 0.0377(7) Uani 1 1 d . . .
N3 N 0.3433(4) 0.5548(3) 0.73061(18) 0.0562(8) Uani 1 1 d . . .
N4 N -0.0639(4) 0.7999(2) 0.8931(2) 0.0486(7) Uani 1 1 d . . .
C4 C 0.1847(4) 0.6026(3) 0.7708(2) 0.0363(7) Uani 1 1 d . . .
N5 N 0.2266(3) 0.5408(2) 0.93390(17) 0.0444(7) Uani 1 1 d . . .
C5 C 0.0822(5) 0.6321(3) 0.7029(2) 0.0400(8) Uani 1 1 d . . .
N6 N 0.0544(4) 0.6755(3) 1.01563(17) 0.0514(7) Uani 1 1 d . . .
C6 C 0.3426(5) 0.4327(3) 0.9187(2) 0.0586(10) Uani 1 1 d . . .
H6A H 0.3715 0.3955 0.9774 0.088 Uiso 1 1 calc R . .
H6B H 0.4492 0.4508 0.8780 0.088 Uiso 1 1 calc R . .
H6C H 0.2839 0.3802 0.8907 0.088 Uiso 1 1 calc R . .
C7 C 0.1444(4) 0.6145(3) 0.5319(2) 0.0361(7) Uani 1 1 d . . .
C8 C 0.0214(4) 0.7039(3) 0.5067(2) 0.0449(8) Uani 1 1 d . . .
H8A H -0.0393 0.7540 0.5502 0.054 Uiso 1 1 calc R . .
C9 C -0.0115(4) 0.7189(3) 0.4157(2) 0.0481(9) Uani 1 1 d . . .
H9A H -0.0955 0.7790 0.3975 0.058 Uiso 1 1 calc R . .
C10 C 0.0788(4) 0.6459(3) 0.3530(2) 0.0434(8) Uani 1 1 d . . .
C11 C 0.2019(4) 0.5566(3) 0.3776(2) 0.0479(9) Uani 1 1 d . . .
H11A H 0.2625 0.5068 0.3339 0.057 Uiso 1 1 calc R . .
C12 C 0.2352(4) 0.5412(3) 0.4685(2) 0.0438(8) Uani 1 1 d . . .
H12A H 0.3193 0.4810 0.4865 0.053 Uiso 1 1 calc R . .
Cl1A Cl 0.44729(15) 0.82758(9) 0.13267(6) 0.0742(3) Uani 1 1 d . A .
N1A N 0.3295(3) 0.9060(2) 0.52979(16) 0.0404(6) Uani 1 1 d . . .
O1A O 0.6608(3) 0.6353(2) 0.83642(16) 0.0647(7) Uani 1 1 d . . .
C1A C 0.3279(5) 0.9027(3) 0.9217(2) 0.0545(10) Uani 1 1 d . A .
O2A O 0.6557(3) 0.7223(2) 0.69902(16) 0.0565(6) Uani 1 1 d . . .
C2A C 0.4719(4) 0.8022(3) 0.8196(2) 0.0422(8) Uani 1 1 d . A .
C3A C 0.3656(4) 0.8851(3) 0.7725(2) 0.0375(7) Uani 1 1 d . A .
N4A N 0.6019(3) 0.7150(2) 0.78363(19) 0.0458(7) Uani 1 1 d . . .
C4A C 0.3355(4) 0.9052(3) 0.6762(2) 0.0389(8) Uani 1 1 d . . .
N5A N 0.2726(4) 0.9493(2) 0.84092(17) 0.0457(7) Uani 1 1 d . . .
C5A C 0.4083(5) 0.8512(3) 0.5998(2) 0.0469(9) Uani 1 1 d . A .
N6A N 0.4467(4) 0.8128(3) 0.91229(17) 0.0518(7) Uani 1 1 d . . .
C6A C 0.1454(5) 1.0545(3) 0.8346(2) 0.0586(10) Uani 1 1 d . A .
H6AA H 0.1127 1.0838 0.8949 0.088 Uiso 1 1 calc R . .
H6AB H 0.0418 1.0348 0.8140 0.088 Uiso 1 1 calc R . .
H6AC H 0.1979 1.1142 0.7909 0.088 Uiso 1 1 calc R . .
C7A C 0.3582(4) 0.8847(3) 0.4339(2) 0.0378(8) Uani 1 1 d . A .
C8A C 0.4689(5) 0.7917(3) 0.4031(2) 0.0499(9) Uani 1 1 d . . .
H8AA H 0.5265 0.7401 0.4451 0.060 Uiso 1 1 calc R A .
C9A C 0.4978(5) 0.7721(3) 0.3105(2) 0.0531(9) Uani 1 1 d . A .
H9AA H 0.5750 0.7081 0.2894 0.064 Uiso 1 1 calc R . .
C10A C 0.4110(5) 0.8484(3) 0.2498(2) 0.0449(8) Uani 1 1 d . . .
C11A C 0.2989(4) 0.9416(3) 0.2805(2) 0.0480(9) Uani 1 1 d . A .
H11B H 0.2406 0.9930 0.2385 0.058 Uiso 1 1 calc R . .
C12A C 0.2706(4) 0.9608(3) 0.3731(2) 0.0461(8) Uani 1 1 d . . .
H12B H 0.1932 1.0246 0.3943 0.055 Uiso 1 1 calc R A .
N2A N 0.2419(14) 1.0095(8) 0.5578(8) 0.049(3) Uani 0.50 1 d PU A 1
N3A N 0.2462(13) 1.0117(9) 0.6468(8) 0.050(3) Uani 0.50 1 d PU A 1
N2B N 0.1841(13) 0.9695(9) 0.5653(8) 0.056(3) Uani 0.50 1 d PU A 2
N3B N 0.1886(13) 0.9720(9) 0.6529(8) 0.053(3) Uani 0.50 1 d PU A 2
H1A H 0.275(3) 0.936(2) 0.9784(18) 0.017(6) Uiso 1 1 d . . .
H5 H -0.037(4) 0.655(2) 0.7094(19) 0.037(8) Uiso 1 1 d . . .
H1 H 0.202(4) 0.542(3) 1.073(2) 0.056(10) Uiso 1 1 d . . .
H5A H 0.486(5) 0.793(3) 0.593(3) 0.068(12) Uiso 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
Cl1 C10 1.725(3) . ?
N1 C5 1.319(4) . ?
N1 N2 1.348(3) . ?
N1 C7 1.424(3) . ?
C1 N6 1.293(4) . ?
C1 N5 1.345(4) . ?
C1 H1 0.94(3) . ?
O1 N4 1.204(3) . ?
O2 N4 1.220(3) . ?
N2 N3 1.304(3) . ?
C2 N6 1.357(4) . ?
C2 C3 1.370(4) . ?
C2 N4 1.420(4) . ?
C3 N5 1.371(4) . ?
C3 C4 1.445(4) . ?
N3 C4 1.341(4) . ?
C4 C5 1.356(4) . ?
N5 C6 1.447(4) . ?
C5 H5 0.92(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.364(4) . ?
C7 C8 1.366(4) . ?
C8 C9 1.383(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.354(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.363(4) . ?
C11 C12 1.381(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
Cl1A C10A 1.725(3) . ?
N1A N2B 1.317(11) . ?
N1A C5A 1.332(4) . ?
N1A N2A 1.357(11) . ?
N1A C7A 1.424(4) . ?
O1A N4A 1.218(3) . ?
C1A N6A 1.291(4) . ?
C1A N5A 1.351(4) . ?
C1A H1A 0.96(2) . ?
O2A N4A 1.232(3) . ?
C2A N6A 1.351(4) . ?
C2A C3A 1.374(4) . ?
C2A N4A 1.401(4) . ?
C3A N5A 1.358(4) . ?
C3A C4A 1.451(4) . ?
C4A C5A 1.342(4) . ?
C4A N3B 1.354(10) . ?
C4A N3A 1.382(11) . ?
N5A C6A 1.458(4) . ?
C5A H5A 0.84(3) . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C7A C8A 1.346(4) . ?
C7A C12A 1.371(4) . ?
C8A C9A 1.373(4) . ?
C8A H8AA 0.9300 . ?
C9A C10A 1.366(4) . ?
C9A H9AA 0.9300 . ?
C10A C11A 1.353(4) . ?
C11A C12A 1.371(4) . ?
C11A H11B 0.9300 . ?
C12A H12B 0.9300 . ?
N2A N3A 1.307(16) . ?
N2B N3B 1.289(16) . ?

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
C5 N1 N2 110.6(2) . . ?
C5 N1 C7 130.2(2) . . ?
N2 N1 C7 119.2(2) . . ?
N6 C1 N5 114.6(3) . . ?
N6 C1 H1 124(2) . . ?
N5 C1 H1 122(2) . . ?
N3 N2 N1 106.2(2) . . ?
N6 C2 C3 113.7(3) . . ?
N6 C2 N4 118.4(3) . . ?
C3 C2 N4 127.9(3) . . ?
C2 C3 N5 102.8(3) . . ?
C2 C3 C4 134.8(3) . . ?
N5 C3 C4 122.4(3) . . ?
N2 N3 C4 109.8(2) . . ?
O1 N4 O2 122.9(3) . . ?
O1 N4 C2 119.6(3) . . ?
O2 N4 C2 117.5(3) . . ?
N3 C4 C5 107.5(3) . . ?
N3 C4 C3 121.6(3) . . ?
C5 C4 C3 130.9(3) . . ?
C1 N5 C3 106.7(3) . . ?
C1 N5 C6 125.0(3) . . ?
C3 N5 C6 128.0(3) . . ?
N1 C5 C4 105.9(3) . . ?
N1 C5 H5 124.8(17) . . ?
C4 C5 H5 128.3(18) . . ?
C1 N6 C2 102.2(3) . . ?
N5 C6 H6A 109.5 . . ?
N5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 121.0(3) . . ?
C12 C7 N1 119.8(3) . . ?
C8 C7 N1 119.2(3) . . ?
C7 C8 C9 118.9(3) . . ?
C7 C8 H8A 120.5 . . ?
C9 C8 H8A 120.5 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 Cl1 119.5(2) . . ?
C11 C10 Cl1 119.0(2) . . ?
C10 C11 C12 118.9(3) . . ?
C10 C11 H11A 120.5 . . ?
C12 C11 H11A 120.5 . . ?
C7 C12 C11 119.8(3) . . ?
C7 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
N2B N1A C5A 108.4(6) . . ?
N2B N1A N2A 28.8(6) . . ?
C5A N1A N2A 107.8(5) . . ?
N2B N1A C7A 120.2(5) . . ?
C5A N1A C7A 129.7(3) . . ?
N2A N1A C7A 120.7(5) . . ?
N6A C1A N5A 113.6(3) . . ?
N6A C1A H1A 127.5(14) . . ?
N5A C1A H1A 118.8(15) . . ?
N6A C2A C3A 112.8(3) . . ?
N6A C2A N4A 118.5(3) . . ?
C3A C2A N4A 128.7(3) . . ?
N5A C3A C2A 103.3(3) . . ?
N5A C3A C4A 123.0(3) . . ?
C2A C3A C4A 133.5(3) . . ?
O1A N4A O2A 121.6(3) . . ?
O1A N4A C2A 119.6(3) . . ?
O2A N4A C2A 118.8(3) . . ?
C5A C4A N3B 105.2(5) . . ?
C5A C4A N3A 107.4(5) . . ?
N3B C4A N3A 28.0(5) . . ?
C5A C4A C3A 132.4(3) . . ?
N3B C4A C3A 121.0(5) . . ?
N3A C4A C3A 118.6(5) . . ?
C1A N5A C3A 107.1(3) . . ?
C1A N5A C6A 122.9(3) . . ?
C3A N5A C6A 129.9(3) . . ?
N1A C5A C4A 106.7(3) . . ?
N1A C5A H5A 123(3) . . ?
C4A C5A H5A 131(3) . . ?
C1A N6A C2A 103.2(3) . . ?
N5A C6A H6AA 109.5 . . ?
N5A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
N5A C6A H6AC 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C8A C7A C12A 120.3(3) . . ?
C8A C7A N1A 121.0(3) . . ?
C12A C7A N1A 118.7(3) . . ?
C7A C8A C9A 120.9(3) . . ?
C7A C8A H8AA 119.5 . . ?
C9A C8A H8AA 119.5 . . ?
C10A C9A C8A 118.8(3) . . ?
C10A C9A H9AA 120.6 . . ?
C8A C9A H9AA 120.6 . . ?
C11A C10A C9A 120.6(3) . . ?
C11A C10A Cl1A 119.5(2) . . ?
C9A C10A Cl1A 119.9(3) . . ?
C10A C11A C12A 120.4(3) . . ?
C10A C11A H11B 119.8 . . ?
C12A C11A H11B 119.8 . . ?
C11A C12A C7A 119.1(3) . . ?
C11A C12A H12B 120.5 . . ?
C7A C12A H12B 120.5 . . ?
N3A N2A N1A 108.9(9) . . ?
N2A N3A C4A 106.7(9) . . ?
N3B N2B N1A 107.7(9) . . ?
N2B N3B C4A 109.7(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 N3 0.5(4) . . . . ?
C7 N1 N2 N3 177.5(3) . . . . ?
N6 C2 C3 N5 0.2(4) . . . . ?
N4 C2 C3 N5 176.7(3) . . . . ?
N6 C2 C3 C4 -178.0(3) . . . . ?
N4 C2 C3 C4 -1.4(6) . . . . ?
N1 N2 N3 C4 -0.2(4) . . . . ?
N6 C2 N4 O1 2.5(5) . . . . ?
C3 C2 N4 O1 -173.9(3) . . . . ?
N6 C2 N4 O2 -178.7(3) . . . . ?
C3 C2 N4 O2 4.9(5) . . . . ?
N2 N3 C4 C5 -0.2(4) . . . . ?
N2 N3 C4 C3 -179.6(3) . . . . ?
C2 C3 C4 N3 147.6(4) . . . . ?
N5 C3 C4 N3 -30.2(5) . . . . ?
C2 C3 C4 C5 -31.6(6) . . . . ?
N5 C3 C4 C5 150.6(3) . . . . ?
N6 C1 N5 C3 -0.4(4) . . . . ?
N6 C1 N5 C6 -175.8(3) . . . . ?
C2 C3 N5 C1 0.1(3) . . . . ?
C4 C3 N5 C1 178.5(3) . . . . ?
C2 C3 N5 C6 175.4(3) . . . . ?
C4 C3 N5 C6 -6.2(5) . . . . ?
N2 N1 C5 C4 -0.6(4) . . . . ?
C7 N1 C5 C4 -177.2(3) . . . . ?
N3 C4 C5 N1 0.5(4) . . . . ?
C3 C4 C5 N1 179.8(3) . . . . ?
N5 C1 N6 C2 0.4(4) . . . . ?
C3 C2 N6 C1 -0.3(4) . . . . ?
N4 C2 N6 C1 -177.3(3) . . . . ?
C5 N1 C7 C12 -156.7(3) . . . . ?
N2 N1 C7 C12 27.0(4) . . . . ?
C5 N1 C7 C8 25.2(5) . . . . ?
N2 N1 C7 C8 -151.1(3) . . . . ?
C12 C7 C8 C9 0.6(5) . . . . ?
N1 C7 C8 C9 178.6(3) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C8 C9 C10 Cl1 -179.5(3) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
Cl1 C10 C11 C12 179.6(3) . . . . ?
C8 C7 C12 C11 -0.5(5) . . . . ?
N1 C7 C12 C11 -178.5(3) . . . . ?
C10 C11 C12 C7 0.4(5) . . . . ?
N6A C2A C3A N5A 0.4(4) . . . . ?
N4A C2A C3A N5A -177.0(3) . . . . ?
N6A C2A C3A C4A -175.3(3) . . . . ?
N4A C2A C3A C4A 7.3(6) . . . . ?
N6A C2A N4A O1A 16.1(5) . . . . ?
C3A C2A N4A O1A -166.6(3) . . . . ?
N6A C2A N4A O2A -162.7(3) . . . . ?
C3A C2A N4A O2A 14.5(5) . . . . ?
N5A C3A C4A C5A -178.3(3) . . . . ?
C2A C3A C4A C5A -3.2(6) . . . . ?
N5A C3A C4A N3B -14.1(7) . . . . ?
C2A C3A C4A N3B 161.0(6) . . . . ?
N5A C3A C4A N3A 18.2(6) . . . . ?
C2A C3A C4A N3A -166.7(5) . . . . ?
N6A C1A N5A C3A -1.0(4) . . . . ?
N6A C1A N5A C6A -177.0(3) . . . . ?
C2A C3A N5A C1A 0.3(3) . . . . ?
C4A C3A N5A C1A 176.6(3) . . . . ?
C2A C3A N5A C6A 176.0(3) . . . . ?
C4A C3A N5A C6A -7.7(5) . . . . ?
N2B N1A C5A C4A -15.7(6) . . . . ?
N2A N1A C5A C4A 14.7(6) . . . . ?
C7A N1A C5A C4A 179.3(3) . . . . ?
N3B C4A C5A N1A 13.6(5) . . . . ?
N3A C4A C5A N1A -15.5(5) . . . . ?
C3A C4A C5A N1A 179.6(3) . . . . ?
N5A C1A N6A C2A 1.2(4) . . . . ?
C3A C2A N6A C1A -1.0(4) . . . . ?
N4A C2A N6A C1A 176.7(3) . . . . ?
N2B N1A C7A C8A -157.5(6) . . . . ?
C5A N1A C7A C8A 6.0(5) . . . . ?
N2A N1A C7A C8A 169.0(5) . . . . ?
N2B N1A C7A C12A 22.5(7) . . . . ?
C5A N1A C7A C12A -174.1(3) . . . . ?
N2A N1A C7A C12A -11.1(6) . . . . ?
C12A C7A C8A C9A 0.7(5) . . . . ?
N1A C7A C8A C9A -179.3(3) . . . . ?
C7A C8A C9A C10A -0.4(5) . . . . ?
C8A C9A C10A C11A 0.1(5) . . . . ?
C8A C9A C10A Cl1A 178.9(3) . . . . ?
C9A C10A C11A C12A 0.0(5) . . . . ?
Cl1A C10A C11A C12A -178.9(3) . . . . ?
C10A C11A C12A C7A 0.3(5) . . . . ?
C8A C7A C12A C11A -0.7(5) . . . . ?
N1A C7A C12A C11A 179.4(3) . . . . ?
N2B N1A N2A N3A 88(2) . . . . ?
C5A N1A N2A N3A -8.2(9) . . . . ?
C7A N1A N2A N3A -174.6(6) . . . . ?
N1A N2A N3A C4A -1.4(10) . . . . ?
C5A C4A N3A N2A 10.5(9) . . . . ?
N3B C4A N3A N2A -79.3(18) . . . . ?
C3A C4A N3A N2A 177.8(6) . . . . ?
C5A N1A N2B N3B 11.3(10) . . . . ?
N2A N1A N2B N3B -82.4(18) . . . . ?
C7A N1A N2B N3B 178.0(6) . . . . ?
N1A N2B N3B C4A -2.6(11) . . . . ?
C5A C4A N3B N2B -7.0(9) . . . . ?
N3A C4A N3B N2B 92(2) . . . . ?
C3A C4A N3B N2B -175.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_dc1
_database_code_depnum_ccdc_archive 'CCDC 1580079'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 N5, 0.5 (H2 O)'
_chemical_formula_sum            'C17 H22 N5 O2.50'
_chemical_formula_weight         336.40

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'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pccn

loop_
_symmetry_equiv_pos_as_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                   16.928(12)
_cell_length_b                   17.377(3)
_cell_length_c                   12.031(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3539(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    972
_cell_measurement_theta_min      3.6338
_cell_measurement_theta_max      65.2383

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1432
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_min  0.47693
_exptl_absorpt_correction_T_max  1.50577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15958
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_av_sigmaI/netI    0.1455
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         65.81
_reflns_number_total             2969
_reflns_number_gt                1034
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0050P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2969
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0936(2) 0.64749(18) 0.6257(3) 0.0494(9) Uani 1 1 d . . .
O1 O -0.01407(17) 0.60188(15) 0.92626(19) 0.0698(10) Uani 1 1 d . . .
O1S O 0.2500 0.7500 0.9521(2) 0.0813(13) Uani 1 2 d S . .
H1SB H 0.2157 0.7274 0.9103 0.098 Uiso 1 1 d R . .
C1 C 0.0904(2) 0.62595(19) 0.5077(3) 0.0676(13) Uani 1 1 d . . .
H1A H 0.1410 0.6349 0.4740 0.101 Uiso 1 1 calc R . .
H1B H 0.0511 0.6564 0.4707 0.101 Uiso 1 1 calc R . .
H1C H 0.0771 0.5724 0.5012 0.101 Uiso 1 1 calc R . .
N2 N -0.01295(18) 0.56885(18) 0.6831(2) 0.0482(9) Uani 1 1 d . . .
O2 O 0.06531(17) 0.69331(14) 0.9828(2) 0.0779(10) Uani 1 1 d . . .
C2 C 0.1429(3) 0.6987(2) 0.6737(4) 0.0569(13) Uani 1 1 d . . .
N3 N 0.13185(19) 0.70590(19) 0.7810(2) 0.0586(11) Uani 1 1 d . . .
C3 C -0.0268(2) 0.5057(2) 0.7383(3) 0.0443(10) Uani 1 1 d . . .
C17 C -0.2418(2) 0.4857(2) 0.8520(3) 0.0891(17) Uani 1 1 d . . .
H17A H -0.2695 0.5073 0.9153 0.107 Uiso 1 1 calc R . .
H17B H -0.2790 0.4540 0.8110 0.107 Uiso 1 1 calc R . .
N4 N -0.09752(19) 0.47325(18) 0.7308(2) 0.0484(9) Uani 1 1 d . . .
C4 C 0.0747(2) 0.6544(2) 0.8019(3) 0.0512(12) Uani 1 1 d . . .
C5 C 0.0472(2) 0.6153(2) 0.7084(3) 0.0444(10) Uani 1 1 d . . .
N5 N 0.0394(2) 0.6485(2) 0.9104(3) 0.0579(11) Uani 1 1 d . . .
C6 C 0.03718(19) 0.46234(19) 0.8018(2) 0.0478(11) Uani 1 1 d . . .
H6A H 0.0813 0.4969 0.8143 0.057 Uiso 1 1 calc R . .
H6B H 0.0164 0.4478 0.8739 0.057 Uiso 1 1 calc R . .
C7 C 0.0675(2) 0.3904(2) 0.7436(3) 0.0489(11) Uani 1 1 d . . .
C8 C 0.0781(3) 0.3236(2) 0.7994(3) 0.0735(15) Uani 1 1 d . . .
H8A H 0.0644 0.3208 0.8741 0.088 Uiso 1 1 calc R . .
C9 C 0.1090(3) 0.2595(3) 0.7473(4) 0.0909(18) Uani 1 1 d . . .
H9A H 0.1157 0.2140 0.7869 0.109 Uiso 1 1 calc R . .
C10 C 0.1297(3) 0.2631(3) 0.6366(4) 0.0804(17) Uani 1 1 d . . .
H10A H 0.1502 0.2199 0.6011 0.097 Uiso 1 1 calc R . .
C11 C 0.1199(3) 0.3301(2) 0.5795(3) 0.0726(15) Uani 1 1 d . . .
H11A H 0.1346 0.3330 0.5052 0.087 Uiso 1 1 calc R . .
C12 C 0.0879(2) 0.3942(2) 0.6320(3) 0.0595(12) Uani 1 1 d . . .
H12A H 0.0802 0.4395 0.5924 0.071 Uiso 1 1 calc R . .
C13 C -0.1248(2) 0.4075(2) 0.7956(3) 0.0591(12) Uani 1 1 d . . .
H13A H -0.0798 0.3787 0.8230 0.071 Uiso 1 1 calc R . .
H13B H -0.1560 0.3737 0.7488 0.071 Uiso 1 1 calc R . .
C14 C -0.1749(2) 0.4356(2) 0.8934(3) 0.0782(16) Uani 1 1 d . . .
H14A H -0.1962 0.3917 0.9332 0.094 Uiso 1 1 calc R . .
H14B H -0.1421 0.4647 0.9444 0.094 Uiso 1 1 calc R . .
C15 C -0.1631(2) 0.5173(2) 0.6819(3) 0.0601(12) Uani 1 1 d . . .
H15A H -0.1954 0.4839 0.6360 0.072 Uiso 1 1 calc R . .
H15B H -0.1425 0.5584 0.6355 0.072 Uiso 1 1 calc R . .
C16 C -0.2131(2) 0.5514(2) 0.7767(3) 0.0754(15) Uani 1 1 d . . .
H16A H -0.1817 0.5874 0.8196 0.090 Uiso 1 1 calc R . .
H16B H -0.2581 0.5788 0.7463 0.090 Uiso 1 1 calc R . .
H2 H 0.1799(14) 0.7316(16) 0.641(2) 0.044(12) Uiso 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
N1 C2 1.350(5) . ?
N1 C5 1.386(4) . ?
N1 C1 1.470(4) . ?
O1 N5 1.231(3) . ?
O1S H1SB 0.8631 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C3 1.304(4) . ?
N2 C5 1.334(4) . ?
O2 N5 1.248(4) . ?
C2 N3 1.310(5) . ?
C2 H2 0.93(2) . ?
N3 C4 1.342(4) . ?
C3 N4 1.327(4) . ?
C3 C6 1.524(4) . ?
C17 C14 1.514(4) . ?
C17 C16 1.536(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
N4 C13 1.457(4) . ?
N4 C15 1.472(4) . ?
C4 C5 1.394(5) . ?
C4 N5 1.439(4) . ?
C6 C7 1.522(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.353(5) . ?
C7 C12 1.387(5) . ?
C8 C9 1.380(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.378(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.363(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.530(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.539(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 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
C2 N1 C5 108.0(3) . . ?
C2 N1 C1 127.2(4) . . ?
C5 N1 C1 124.8(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 N2 C5 122.1(3) . . ?
N3 C2 N1 113.3(4) . . ?
N3 C2 H2 117(2) . . ?
N1 C2 H2 130(2) . . ?
C2 N3 C4 102.9(3) . . ?
N2 C3 N4 119.0(4) . . ?
N2 C3 C6 122.9(3) . . ?
N4 C3 C6 117.7(3) . . ?
C14 C17 C16 112.6(3) . . ?
C14 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C14 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C3 N4 C13 125.6(3) . . ?
C3 N4 C15 119.1(3) . . ?
C13 N4 C15 112.5(3) . . ?
N3 C4 C5 114.5(4) . . ?
N3 C4 N5 121.1(4) . . ?
C5 C4 N5 124.0(4) . . ?
N2 C5 N1 120.9(4) . . ?
N2 C5 C4 137.2(4) . . ?
N1 C5 C4 101.1(3) . . ?
O1 N5 O2 124.1(4) . . ?
O1 N5 C4 119.5(4) . . ?
O2 N5 C4 116.4(3) . . ?
C7 C6 C3 114.5(3) . . ?
C7 C6 H6A 108.6 . . ?
C3 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C3 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C12 119.2(4) . . ?
C8 C7 C6 121.4(4) . . ?
C12 C7 C6 119.3(4) . . ?
C7 C8 C9 121.1(4) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C11 C10 C9 119.6(5) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C7 C12 C11 119.9(4) . . ?
C7 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
N4 C13 C14 109.7(3) . . ?
N4 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N4 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C17 C14 C13 110.1(3) . . ?
C17 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C17 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 C16 108.6(3) . . ?
N4 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
N4 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
C17 C16 C15 109.0(3) . . ?
C17 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?

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 C2 N3 -2.3(6) . . . . ?
C1 N1 C2 N3 -180.0(4) . . . . ?
N1 C2 N3 C4 2.4(6) . . . . ?
C5 N2 C3 N4 161.7(3) . . . . ?
C5 N2 C3 C6 -24.9(5) . . . . ?
N2 C3 N4 C13 -173.3(3) . . . . ?
C6 C3 N4 C13 12.9(5) . . . . ?
N2 C3 N4 C15 -13.5(5) . . . . ?
C6 C3 N4 C15 172.8(3) . . . . ?
C2 N3 C4 C5 -1.7(5) . . . . ?
C2 N3 C4 N5 -174.3(4) . . . . ?
C3 N2 C5 N1 137.3(4) . . . . ?
C3 N2 C5 C4 -55.1(7) . . . . ?
C2 N1 C5 N2 172.6(4) . . . . ?
C1 N1 C5 N2 -9.7(6) . . . . ?
C2 N1 C5 C4 1.1(4) . . . . ?
C1 N1 C5 C4 178.8(4) . . . . ?
N3 C4 C5 N2 -168.9(5) . . . . ?
N5 C4 C5 N2 3.5(8) . . . . ?
N3 C4 C5 N1 0.4(5) . . . . ?
N5 C4 C5 N1 172.7(4) . . . . ?
N3 C4 N5 O1 178.4(4) . . . . ?
C5 C4 N5 O1 6.5(6) . . . . ?
N3 C4 N5 O2 -0.5(6) . . . . ?
C5 C4 N5 O2 -172.4(4) . . . . ?
N2 C3 C6 C7 -103.0(4) . . . . ?
N4 C3 C6 C7 70.5(4) . . . . ?
C3 C6 C7 C8 -135.2(4) . . . . ?
C3 C6 C7 C12 47.6(5) . . . . ?
C12 C7 C8 C9 0.1(7) . . . . ?
C6 C7 C8 C9 -177.1(4) . . . . ?
C7 C8 C9 C10 0.2(8) . . . . ?
C8 C9 C10 C11 0.3(8) . . . . ?
C9 C10 C11 C12 -1.1(8) . . . . ?
C8 C7 C12 C11 -0.9(7) . . . . ?
C6 C7 C12 C11 176.4(3) . . . . ?
C10 C11 C12 C7 1.4(7) . . . . ?
C3 N4 C13 C14 98.7(4) . . . . ?
C15 N4 C13 C14 -62.2(4) . . . . ?
C16 C17 C14 C13 -52.7(5) . . . . ?
N4 C13 C14 C17 55.1(5) . . . . ?
C3 N4 C15 C16 -98.9(4) . . . . ?
C13 N4 C15 C16 63.5(4) . . . . ?
C14 C17 C16 C15 53.9(5) . . . . ?
N4 C15 C16 C17 -57.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        65.81
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_dc1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1826375'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H5 N5 O2'
_chemical_formula_sum            'C5 H5 N5 O2'
_chemical_formula_weight         167.14

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0876(8)
_cell_length_b                   9.8869(13)
_cell_length_c                   11.4194(15)
_cell_angle_alpha                89.761(16)
_cell_angle_beta                 73.244(11)
_cell_angle_gamma                69.093(12)
_cell_volume                     711.41(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3344
_cell_measurement_theta_min      2.7275
_cell_measurement_theta_max      33.5689

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_min  0.80715
_exptl_absorpt_correction_T_max  1.27235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12432
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0802
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         33.60
_reflns_number_total             4869
_reflns_number_gt                1997
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0199P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4869
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.21302(15) 0.68666(10) 0.54258(9) 0.0368(3) Uani 1 1 d . . .
C1A C 0.1913(2) 0.83498(14) 0.57494(13) 0.0535(4) Uani 1 1 d . . .
H1AA H 0.2040 0.8434 0.6558 0.080 Uiso 1 1 calc R . .
H1AB H 0.0548 0.9016 0.5738 0.080 Uiso 1 1 calc R . .
H1AC H 0.3006 0.8578 0.5165 0.080 Uiso 1 1 calc R . .
O1A O 0.1808(2) 0.82058(11) 0.33220(10) 0.0922(4) Uani 1 1 d . . .
N1 N 0.75999(17) 0.81711(11) 0.12529(9) 0.0435(3) Uani 1 1 d . . .
O1 O 0.82230(19) 0.68130(11) -0.10193(9) 0.0748(3) Uani 1 1 d . . .
C1 C 0.7775(3) 0.66932(14) 0.14949(14) 0.0665(5) Uani 1 1 d . . .
H1A H 0.7606 0.6602 0.2353 0.100 Uiso 1 1 calc R . .
H1B H 0.9144 0.6020 0.1013 0.100 Uiso 1 1 calc R . .
H1C H 0.6690 0.6481 0.1278 0.100 Uiso 1 1 calc R . .
C2A C 0.2372(2) 0.58144(15) 0.61592(13) 0.0412(3) Uani 1 1 d . . .
O2A O 0.22452(19) 0.61880(11) 0.23753(9) 0.0735(3) Uani 1 1 d . . .
N2A N 0.20937(19) 0.69091(13) 0.32969(11) 0.0526(3) Uani 1 1 d . . .
O2 O 0.78874(17) 0.88402(11) -0.18146(9) 0.0643(3) Uani 1 1 d . . .
N2 N 0.79338(17) 0.81177(13) -0.09401(10) 0.0463(3) Uani 1 1 d . . .
C2 C 0.7318(2) 0.92191(16) 0.20869(14) 0.0526(4) Uani 1 1 d . . .
N3A N 0.26360(16) 0.45392(11) 0.56578(9) 0.0397(3) Uani 1 1 d . . .
C3A C 0.2779(2) 0.36295(14) 0.36503(13) 0.0424(3) Uani 1 1 d . . .
N3 N 0.71654(18) 1.04829(11) 0.16665(10) 0.0472(3) Uani 1 1 d . . .
C3 C 0.7291(2) 1.13739(14) -0.03235(14) 0.0450(3) Uani 1 1 d . . .
N4A N 0.29731(17) 0.23711(13) 0.40532(10) 0.0450(3) Uani 1 1 d . . .
C4A C 0.25639(18) 0.47629(13) 0.44926(11) 0.0332(3) Uani 1 1 d . . .
C4 C 0.73646(18) 1.02590(13) 0.04573(11) 0.0360(3) Uani 1 1 d . . .
N4 N 0.70323(19) 1.26421(13) 0.01722(11) 0.0543(3) Uani 1 1 d . . .
C5A C 0.22500(18) 0.62027(13) 0.43332(11) 0.0348(3) Uani 1 1 d . . .
N5A N 0.3149(2) 0.12975(14) 0.44189(12) 0.0661(4) Uani 1 1 d . . .
C5 C 0.76406(19) 0.88297(13) 0.01829(11) 0.0364(3) Uani 1 1 d . . .
N5 N 0.6821(3) 1.37109(15) 0.06146(14) 0.0888(5) Uani 1 1 d . . .
H2A H 0.2366(17) 0.6006(12) 0.6955(11) 0.037(3) Uiso 1 1 d . . .
H2 H 0.720(2) 0.8988(14) 0.2918(13) 0.060(4) Uiso 1 1 d . . .
H3A H 0.273(2) 0.3699(13) 0.2869(12) 0.053(4) Uiso 1 1 d . . .
H3 H 0.749(2) 1.1271(14) -0.1188(13) 0.064(4) Uiso 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
N1A C2A 1.3271(16) . ?
N1A C5A 1.3786(15) . ?
N1A C1A 1.4564(15) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
O1A N2A 1.2235(13) . ?
N1 C2 1.3309(16) . ?
N1 C5 1.3800(15) . ?
N1 C1 1.4538(16) . ?
O1 N2 1.2312(13) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2A N3A 1.3146(15) . ?
C2A H2A 0.928(12) . ?
O2A N2A 1.2304(13) . ?
N2A C5A 1.3834(16) . ?
O2 N2 1.2267(13) . ?
N2 C5 1.3902(15) . ?
C2 N3 1.3160(17) . ?
C2 H2 0.963(14) . ?
N3A C4A 1.3604(14) . ?
C3A N4A 1.2993(17) . ?
C3A C4A 1.4164(17) . ?
C3A H3A 0.906(13) . ?
N3 C4 1.3578(15) . ?
C3 N4 1.3070(17) . ?
C3 C4 1.4108(18) . ?
C3 H3 0.956(14) . ?
N4A N5A 1.1174(15) . ?
C4A C5A 1.3800(16) . ?
C4 C5 1.3801(16) . ?
N4 N5 1.1145(15) . ?

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 N1A C5A 104.47(10) . . ?
C2A N1A C1A 125.09(11) . . ?
C5A N1A C1A 130.36(11) . . ?
N1A C1A H1AA 109.5 . . ?
N1A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
N1A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C2 N1 C5 104.34(11) . . ?
C2 N1 C1 125.08(12) . . ?
C5 N1 C1 130.57(11) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3A C2A N1A 114.83(12) . . ?
N3A C2A H2A 125.1(7) . . ?
N1A C2A H2A 120.1(7) . . ?
O1A N2A O2A 122.49(12) . . ?
O1A N2A C5A 119.93(12) . . ?
O2A N2A C5A 117.58(11) . . ?
O2 N2 O1 123.04(11) . . ?
O2 N2 C5 117.35(11) . . ?
O1 N2 C5 119.61(12) . . ?
N3 C2 N1 114.66(13) . . ?
N3 C2 H2 127.6(8) . . ?
N1 C2 H2 117.7(7) . . ?
C2A N3A C4A 104.72(10) . . ?
N4A C3A C4A 116.98(13) . . ?
N4A C3A H3A 116.0(8) . . ?
C4A C3A H3A 126.9(8) . . ?
C2 N3 C4 104.90(11) . . ?
N4 C3 C4 116.68(13) . . ?
N4 C3 H3 117.2(8) . . ?
C4 C3 H3 126.0(8) . . ?
N5A N4A C3A 178.62(15) . . ?
N3A C4A C5A 108.79(10) . . ?
N3A C4A C3A 121.88(11) . . ?
C5A C4A C3A 129.33(12) . . ?
N3 C4 C5 108.81(11) . . ?
N3 C4 C3 122.12(11) . . ?
C5 C4 C3 129.07(12) . . ?
N5 N4 C3 178.61(16) . . ?
N1A C5A C4A 107.19(11) . . ?
N1A C5A N2A 123.99(11) . . ?
C4A C5A N2A 128.81(12) . . ?
N1 C5 C4 107.29(11) . . ?
N1 C5 N2 123.96(11) . . ?
C4 C5 N2 128.74(12) . . ?

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 C2A N3A 0.02(15) . . . . ?
C1A N1A C2A N3A -177.00(12) . . . . ?
C5 N1 C2 N3 0.24(17) . . . . ?
C1 N1 C2 N3 -178.84(13) . . . . ?
N1A C2A N3A C4A 0.00(15) . . . . ?
N1 C2 N3 C4 -0.10(17) . . . . ?
C4A C3A N4A N5A -16(6) . . . . ?
C2A N3A C4A C5A -0.02(14) . . . . ?
C2A N3A C4A C3A -179.65(12) . . . . ?
N4A C3A C4A N3A 2.44(18) . . . . ?
N4A C3A C4A C5A -177.10(12) . . . . ?
C2 N3 C4 C5 -0.08(15) . . . . ?
C2 N3 C4 C3 -179.81(12) . . . . ?
N4 C3 C4 N3 0.38(19) . . . . ?
N4 C3 C4 C5 -179.28(14) . . . . ?
C4 C3 N4 N5 14(7) . . . . ?
C2A N1A C5A C4A -0.03(13) . . . . ?
C1A N1A C5A C4A 176.76(11) . . . . ?
C2A N1A C5A N2A -179.43(11) . . . . ?
C1A N1A C5A N2A -2.6(2) . . . . ?
N3A C4A C5A N1A 0.03(14) . . . . ?
C3A C4A C5A N1A 179.63(12) . . . . ?
N3A C4A C5A N2A 179.39(11) . . . . ?
C3A C4A C5A N2A -1.0(2) . . . . ?
O1A N2A C5A N1A -0.9(2) . . . . ?
O2A N2A C5A N1A 179.38(12) . . . . ?
O1A N2A C5A C4A 179.86(13) . . . . ?
O2A N2A C5A C4A 0.1(2) . . . . ?
C2 N1 C5 C4 -0.28(14) . . . . ?
C1 N1 C5 C4 178.73(13) . . . . ?
C2 N1 C5 N2 179.15(12) . . . . ?
C1 N1 C5 N2 -1.8(2) . . . . ?
N3 C4 C5 N1 0.23(14) . . . . ?
C3 C4 C5 N1 179.93(12) . . . . ?
N3 C4 C5 N2 -179.16(12) . . . . ?
C3 C4 C5 N2 0.5(2) . . . . ?
O2 N2 C5 N1 178.35(11) . . . . ?
O1 N2 C5 N1 -1.60(19) . . . . ?
O2 N2 C5 C4 -2.4(2) . . . . ?
O1 N2 C5 C4 177.69(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.867
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.036
