# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2048904'
loop_
_audit_author_name
_audit_author_address
'Matti Haukka'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-02-04 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         'C17 H19 N5 O'
_chemical_formula_sum            'C17 H19 N5 O'
_chemical_formula_weight         309.37

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      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                   11.5093(2)
_cell_length_b                   13.0753(2)
_cell_length_c                   10.9809(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.310(2)
_cell_angle_gamma                90
_cell_volume                     1528.79(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9515
_cell_measurement_theta_min      3.3810
_cell_measurement_theta_max      76.5750

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   micro-source
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_reflns_number            16866
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.152
_diffrn_reflns_theta_max         76.938
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3225
_reflns_number_gt                3001
_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       
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2017)'
_computing_molecular_graphics    
'CrystaMaker X (CrystalMaker Software ltd., 2018)'
_computing_publication_material  'SHELXL-2017 (Sheldrick, 2017)'
_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)+(0.0549P)²+0.4226P] 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         3225
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
O1 O 0.60400(7) 0.99646(5) 0.25322(7) 0.02124(17) Uani 1 1 d . . . . .
N1 N 0.85091(8) 0.67619(7) 0.43157(8) 0.01835(19) Uani 1 1 d . . . . .
N2 N 0.92018(8) 0.63481(7) 0.55013(9) 0.0220(2) Uani 1 1 d . . . . .
N3 N 0.95831(9) 0.71092(8) 0.63374(9) 0.0249(2) Uani 1 1 d . . . . .
N4 N 0.64166(8) 0.82605(6) 0.26241(8) 0.01816(19) Uani 1 1 d . . . . .
N5 N 0.47017(8) 0.70789(6) 0.17442(9) 0.01884(19) Uani 1 1 d . . . . .
H5A H 0.4477(15) 0.6418(13) 0.1858(16) 0.036(4) Uiso 1 1 d . . . . .
C1 C 0.68122(9) 0.64287(7) 0.22391(10) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.63635(9) 0.58903(7) 0.10538(10) 0.0190(2) Uani 1 1 d . . . . .
H2 H 0.558353 0.607807 0.038781 0.023 Uiso 1 1 calc R U . . .
C3 C 0.70488(10) 0.50782(8) 0.08360(10) 0.0209(2) Uani 1 1 d . . . . .
H3 H 0.673337 0.471871 0.002369 0.025 Uiso 1 1 calc R U . . .
C4 C 0.81919(10) 0.47932(8) 0.18033(10) 0.0204(2) Uani 1 1 d . . . . .
H4 H 0.863360 0.421811 0.166889 0.025 Uiso 1 1 calc R U . . .
C5 C 0.86871(9) 0.53495(8) 0.29654(10) 0.0192(2) Uani 1 1 d . . . . .
H5 H 0.948300 0.517893 0.361614 0.023 Uiso 1 1 calc R U . . .
C6 C 0.79957(9) 0.61593(7) 0.31564(10) 0.0175(2) Uani 1 1 d . . . . .
C7 C 0.91365(10) 0.80001(9) 0.56914(11) 0.0237(2) Uani 1 1 d . . . . .
H7 H 0.928528 0.866117 0.607930 0.028 Uiso 1 1 calc R U . . .
C8 C 0.84381(9) 0.77964(8) 0.43937(10) 0.0194(2) Uani 1 1 d . . . . .
C9 C 0.77809(9) 0.84434(8) 0.32085(10) 0.0202(2) Uani 1 1 d . . . . .
H9A H 0.793387 0.917301 0.345952 0.024 Uiso 1 1 calc R U . . .
H9B H 0.814233 0.830285 0.253872 0.024 Uiso 1 1 calc R U . . .
C10 C 0.56312(9) 0.90820(7) 0.23517(9) 0.0169(2) Uani 1 1 d . . . . .
C11 C 0.42309(9) 0.88767(7) 0.17513(9) 0.0176(2) Uani 1 1 d . . . . .
H11 H 0.381249 0.938272 0.213414 0.021 Uiso 1 1 calc R U . . .
C12 C 0.37627(10) 0.90812(8) 0.02598(10) 0.0221(2) Uani 1 1 d . . . . .
H12A H 0.391422 0.980679 0.010838 0.027 Uiso 1 1 calc R U . . .
H12B H 0.424193 0.865149 -0.012837 0.027 Uiso 1 1 calc R U . . .
C13 C 0.23617(10) 0.88450(9) -0.04194(10) 0.0251(2) Uani 1 1 d . . . . .
H13A H 0.187437 0.931761 -0.009098 0.030 Uiso 1 1 calc R U . . .
H13B H 0.209470 0.895154 -0.137987 0.030 Uiso 1 1 calc R U . . .
C14 C 0.20921(10) 0.77440(8) -0.01521(11) 0.0251(2) Uani 1 1 d . . . . .
H14A H 0.253643 0.727107 -0.053216 0.030 Uiso 1 1 calc R U . . .
H14B H 0.118006 0.760842 -0.058381 0.030 Uiso 1 1 calc R U . . .
C15 C 0.25189(9) 0.75470(8) 0.13263(11) 0.0234(2) Uani 1 1 d . . . . .
H15A H 0.199743 0.796052 0.167975 0.028 Uiso 1 1 calc R U . . .
H15B H 0.238089 0.681716 0.147066 0.028 Uiso 1 1 calc R U . . .
C16 C 0.39010(9) 0.78084(7) 0.20824(10) 0.0188(2) Uani 1 1 d . . . . .
H16 H 0.409099 0.776719 0.304846 0.023 Uiso 1 1 calc R U . . .
C17 C 0.59994(9) 0.71886(7) 0.26196(10) 0.0171(2) Uani 1 1 d . . . . .
H17 H 0.606300 0.701737 0.353032 0.021 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 C10 1.2336(12) . yes
N1 N2 1.3547(12) . yes
N1 C8 1.3598(13) . yes
N1 C6 1.4210(13) . yes
N2 N3 1.3115(13) . yes
N3 C7 1.3592(15) . yes
N4 C10 1.3620(12) . yes
N4 C9 1.4729(12) . yes
N4 C17 1.4810(12) . yes
N5 C17 1.4441(12) . yes
N5 C16 1.4686(12) . yes
N5 H5A 0.924(17) . ?
C1 C2 1.3950(14) . ?
C1 C6 1.3972(14) . ?
C1 C17 1.5277(13) . ?
C2 C3 1.3964(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3918(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3894(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3875(14) . ?
C5 H5 0.9500 . ?
C7 C8 1.3704(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.4947(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5157(13) . ?
C11 C16 1.5273(13) . ?
C11 C12 1.5408(14) . ?
C11 H11 1.0000 . ?
C12 C13 1.5293(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5245(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5290(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5276(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16 1.0000 . ?
C17 H17 1.0000 . ?

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
N2 N1 C8 111.36(8) . . ?
N2 N1 C6 122.17(8) . . ?
C8 N1 C6 126.40(9) . . ?
N3 N2 N1 106.75(8) . . ?
N2 N3 C7 108.98(9) . . ?
C10 N4 C9 118.46(8) . . ?
C10 N4 C17 123.94(8) . . ?
C9 N4 C17 116.47(8) . . ?
C17 N5 C16 110.91(8) . . ?
C17 N5 H5A 106.0(10) . . ?
C16 N5 H5A 109.8(10) . . ?
C2 C1 C6 117.37(9) . . ?
C2 C1 C17 122.35(9) . . ?
C6 C1 C17 119.82(9) . . ?
C1 C2 C3 120.69(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.31(9) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.00(9) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 118.66(9) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 122.78(9) . . ?
C5 C6 N1 119.42(9) . . ?
C1 C6 N1 117.79(9) . . ?
N3 C7 C8 109.42(10) . . ?
N3 C7 H7 125.3 . . ?
C8 C7 H7 125.3 . . ?
N1 C8 C7 103.49(9) . . ?
N1 C8 C9 122.06(9) . . ?
C7 C8 C9 134.31(10) . . ?
N4 C9 C8 113.01(8) . . ?
N4 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
N4 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O1 C10 N4 121.44(9) . . ?
O1 C10 C11 120.88(9) . . ?
N4 C10 C11 117.61(8) . . ?
C10 C11 C16 112.19(8) . . ?
C10 C11 C12 108.46(8) . . ?
C16 C11 C12 113.17(8) . . ?
C10 C11 H11 107.6 . . ?
C16 C11 H11 107.6 . . ?
C12 C11 H11 107.6 . . ?
C13 C12 C11 111.21(9) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 110.54(9) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 110.90(9) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 112.83(9) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
N5 C16 C11 107.30(8) . . ?
N5 C16 C15 109.95(8) . . ?
C11 C16 C15 112.14(8) . . ?
N5 C16 H16 109.1 . . ?
C11 C16 H16 109.1 . . ?
C15 C16 H16 109.1 . . ?
N5 C17 N4 110.39(8) . . ?
N5 C17 C1 109.84(8) . . ?
N4 C17 C1 112.65(8) . . ?
N5 C17 H17 107.9 . . ?
N4 C17 H17 107.9 . . ?
C1 C17 H17 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
C8 N1 N2 N3 -0.43(11) . . . . ?
C6 N1 N2 N3 176.72(9) . . . . ?
N1 N2 N3 C7 0.07(11) . . . . ?
C6 C1 C2 C3 3.48(14) . . . . ?
C17 C1 C2 C3 -168.81(9) . . . . ?
C1 C2 C3 C4 0.11(15) . . . . ?
C2 C3 C4 C5 -3.27(15) . . . . ?
C3 C4 C5 C6 2.65(15) . . . . ?
C4 C5 C6 C1 1.12(15) . . . . ?
C4 C5 C6 N1 -177.53(9) . . . . ?
C2 C1 C6 C5 -4.16(15) . . . . ?
C17 C1 C6 C5 168.34(9) . . . . ?
C2 C1 C6 N1 174.52(8) . . . . ?
C17 C1 C6 N1 -12.99(13) . . . . ?
N2 N1 C6 C5 -37.74(14) . . . . ?
C8 N1 C6 C5 138.96(10) . . . . ?
N2 N1 C6 C1 143.54(9) . . . . ?
C8 N1 C6 C1 -39.77(14) . . . . ?
N2 N3 C7 C8 0.30(12) . . . . ?
N2 N1 C8 C7 0.59(11) . . . . ?
C6 N1 C8 C7 -176.41(9) . . . . ?
N2 N1 C8 C9 176.91(9) . . . . ?
C6 N1 C8 C9 -0.08(15) . . . . ?
N3 C7 C8 N1 -0.53(11) . . . . ?
N3 C7 C8 C9 -176.18(11) . . . . ?
C10 N4 C9 C8 130.51(9) . . . . ?
C17 N4 C9 C8 -37.83(12) . . . . ?
N1 C8 C9 N4 66.03(12) . . . . ?
C7 C8 C9 N4 -118.96(13) . . . . ?
C9 N4 C10 O1 3.10(14) . . . . ?
C17 N4 C10 O1 170.51(9) . . . . ?
C9 N4 C10 C11 -179.97(8) . . . . ?
C17 N4 C10 C11 -12.57(14) . . . . ?
O1 C10 C11 C16 -158.18(9) . . . . ?
N4 C10 C11 C16 24.87(12) . . . . ?
O1 C10 C11 C12 76.07(11) . . . . ?
N4 C10 C11 C12 -100.88(10) . . . . ?
C10 C11 C12 C13 177.62(8) . . . . ?
C16 C11 C12 C13 52.44(11) . . . . ?
C11 C12 C13 C14 -56.58(12) . . . . ?
C12 C13 C14 C15 58.03(12) . . . . ?
C13 C14 C15 C16 -55.23(12) . . . . ?
C17 N5 C16 C11 68.54(10) . . . . ?
C17 N5 C16 C15 -169.25(8) . . . . ?
C10 C11 C16 N5 -51.28(10) . . . . ?
C12 C11 C16 N5 71.86(10) . . . . ?
C10 C11 C16 C15 -172.11(8) . . . . ?
C12 C11 C16 C15 -48.97(11) . . . . ?
C14 C15 C16 N5 -68.90(11) . . . . ?
C14 C15 C16 C11 50.38(12) . . . . ?
C16 N5 C17 N4 -54.69(11) . . . . ?
C16 N5 C17 C1 -179.49(8) . . . . ?
C10 N4 C17 N5 26.68(13) . . . . ?
C9 N4 C17 N5 -165.68(8) . . . . ?
C10 N4 C17 C1 149.87(9) . . . . ?
C9 N4 C17 C1 -42.50(11) . . . . ?
C2 C1 C17 N5 12.49(13) . . . . ?
C6 C1 C17 N5 -159.61(9) . . . . ?
C2 C1 C17 N4 -111.00(10) . . . . ?
C6 C1 C17 N4 76.90(11) . . . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_17c
_database_code_depnum_ccdc_archive 'CCDC 2048906'
loop_
_audit_author_name
_audit_author_address
'Matti Haukka'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-02-04 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         'C18 H16 Br N5 O'
_chemical_formula_sum            'C18 H16 Br N5 O'
_chemical_formula_weight         398.27

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   21.0136(3)
_cell_length_b                   8.39870(10)
_cell_length_c                   18.1668(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.948(2)
_cell_angle_gamma                90
_cell_volume                     3147.85(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8304
_cell_measurement_theta_min      4.2640
_cell_measurement_theta_max      76.3540

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    3.710
_shelx_estimated_absorpt_T_min   0.588
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_reflns_number            12301
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.286
_diffrn_reflns_theta_max         76.778
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3290
_reflns_number_gt                3116
_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       
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2017)'
_computing_molecular_graphics    
'CrystaMaker X (CrystalMaker Software ltd., 2018)'
_computing_publication_material  'SHELXL-2017 (Sheldrick, 2017)'
_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)+(0.0283P)²+3.7644P] 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         3290
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.60470(2) 0.75576(2) 0.28397(2) 0.01888(6) Uani 1 1 d . . . . .
O1 O 0.30714(5) 0.12477(14) 0.34423(7) 0.0263(2) Uani 1 1 d . . . . .
N1 N 0.54552(6) 0.10592(14) 0.39808(6) 0.0143(2) Uani 1 1 d . . . . .
N2 N 0.58937(6) 0.01749(14) 0.44569(7) 0.0175(2) Uani 1 1 d . . . . .
N3 N 0.55968(6) -0.11474(15) 0.45723(7) 0.0198(3) Uani 1 1 d . . . . .
N4 N 0.40678(6) 0.23977(13) 0.36137(7) 0.0134(2) Uani 1 1 d . . . . .
N5 N 0.41952(5) 0.50861(14) 0.40730(7) 0.0139(2) Uani 1 1 d . . . . .
C1 C 0.58767(7) 0.55182(16) 0.32082(7) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.63443(7) 0.43386(18) 0.32637(8) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.675271 0.454113 0.313081 0.021 Uiso 1 1 calc R U . . .
C3 C 0.61969(7) 0.28509(18) 0.35196(8) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.650231 0.200778 0.355224 0.020 Uiso 1 1 calc R U . . .
C4 C 0.56014(7) 0.25966(15) 0.37282(8) 0.0136(3) Uani 1 1 d . . . . .
C5 C 0.51336(6) 0.37981(16) 0.36884(7) 0.0122(2) Uani 1 1 d . . . . .
C6 C 0.52815(6) 0.52739(16) 0.34135(7) 0.0135(2) Uani 1 1 d . . . . .
H6 H 0.497395 0.611454 0.336675 0.016 Uiso 1 1 calc R U . . .
C7 C 0.49755(7) -0.11132(17) 0.41776(8) 0.0181(3) Uani 1 1 d . . . . .
H7 H 0.466196 -0.193048 0.417157 0.022 Uiso 1 1 calc R U . . .
C8 C 0.48790(7) 0.02926(16) 0.37922(8) 0.0145(3) Uani 1 1 d . . . . .
C9 C 0.43282(7) 0.10354(16) 0.32661(8) 0.0157(3) Uani 1 1 d . . . . .
H9A H 0.447808 0.138991 0.280801 0.019 Uiso 1 1 calc R U . . .
H9B H 0.398155 0.023563 0.311729 0.019 Uiso 1 1 calc R U . . .
C10 C 0.34500(7) 0.22558(17) 0.37543(8) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.32693(6) 0.33560(17) 0.43384(8) 0.0150(3) Uani 1 1 d . . . . .
H11 H 0.329696 0.272739 0.481090 0.018 Uiso 1 1 calc R U . . .
C12 C 0.25706(6) 0.40504(18) 0.41359(8) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.220884 0.327686 0.413595 0.021 Uiso 1 1 calc R U . . .
C13 C 0.26340(7) 0.53911(19) 0.47261(8) 0.0204(3) Uani 1 1 d . . . . .
H13A H 0.276498 0.499455 0.524599 0.025 Uiso 1 1 calc R U . . .
H13B H 0.223815 0.605180 0.467924 0.025 Uiso 1 1 calc R U . . .
C14 C 0.31897(7) 0.62410(18) 0.44368(9) 0.0202(3) Uani 1 1 d . . . . .
H14 H 0.333932 0.727284 0.468546 0.024 Uiso 1 1 calc R U . . .
C15 C 0.25374(7) 0.5030(2) 0.34257(8) 0.0217(3) Uani 1 1 d . . . . .
H15 H 0.230279 0.476315 0.294140 0.026 Uiso 1 1 calc R U . . .
C16 C 0.28967(7) 0.63285(19) 0.36054(9) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.295894 0.716247 0.327298 0.028 Uiso 1 1 calc R U . . .
C17 C 0.36975(6) 0.48702(16) 0.45329(8) 0.0150(3) Uani 1 1 d . . . . .
H17 H 0.391503 0.481448 0.507197 0.018 Uiso 1 1 calc R U . . .
C18 C 0.45265(6) 0.35880(15) 0.40276(7) 0.0121(2) Uani 1 1 d . . . . .
H18 H 0.466877 0.318462 0.455092 0.014 Uiso 1 1 calc R U . . .
H5 H 0.3995(9) 0.537(2) 0.3624(11) 0.021(5) 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
Br1 C1 1.8977(13) . yes
O1 C10 1.2246(18) . yes
N1 C8 1.3566(18) . yes
N1 N2 1.3586(16) . yes
N1 C4 1.4233(17) . yes
N2 N3 1.3101(18) . yes
N3 C7 1.365(2) . yes
N4 C10 1.3751(18) . yes
N4 C9 1.4623(17) . yes
N4 C18 1.4894(17) . yes
N5 C18 1.4478(16) . yes
N5 C17 1.4686(17) . yes
N5 H5 0.88(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.3865(19) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.4009(18) . ?
C5 C6 1.3932(19) . ?
C5 C18 1.5289(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.368(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.4907(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5090(19) . ?
C11 C12 1.5575(18) . ?
C11 C17 1.5593(19) . ?
C11 H11 1.0000 . ?
C12 C15 1.520(2) . ?
C12 C13 1.543(2) . ?
C12 H12 1.0000 . ?
C13 C14 1.544(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C16 1.521(2) . ?
C14 C17 1.5569(19) . ?
C14 H14 1.0000 . ?
C15 C16 1.331(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17 1.0000 . ?
C18 H18 1.0000 . ?

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
C8 N1 N2 111.48(11) . . ?
C8 N1 C4 125.88(12) . . ?
N2 N1 C4 122.64(12) . . ?
N3 N2 N1 106.22(11) . . ?
N2 N3 C7 109.57(12) . . ?
C10 N4 C9 117.15(11) . . ?
C10 N4 C18 120.51(11) . . ?
C9 N4 C18 118.94(11) . . ?
C18 N5 C17 109.09(10) . . ?
C18 N5 H5 109.3(13) . . ?
C17 N5 H5 107.2(13) . . ?
C2 C1 C6 122.56(13) . . ?
C2 C1 Br1 119.49(10) . . ?
C6 C1 Br1 117.95(10) . . ?
C1 C2 C3 117.87(13) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C2 C3 C4 119.92(13) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 122.27(13) . . ?
C3 C4 N1 119.18(12) . . ?
C5 C4 N1 118.54(12) . . ?
C6 C5 C4 117.21(12) . . ?
C6 C5 C18 120.47(12) . . ?
C4 C5 C18 121.81(12) . . ?
C1 C6 C5 120.13(12) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N3 C7 C8 108.72(13) . . ?
N3 C7 H7 125.6 . . ?
C8 C7 H7 125.6 . . ?
N1 C8 C7 104.01(12) . . ?
N1 C8 C9 120.69(12) . . ?
C7 C8 C9 135.30(13) . . ?
N4 C9 C8 111.05(11) . . ?
N4 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N4 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O1 C10 N4 121.82(13) . . ?
O1 C10 C11 121.38(13) . . ?
N4 C10 C11 116.75(12) . . ?
C10 C11 C12 114.52(11) . . ?
C10 C11 C17 116.57(11) . . ?
C12 C11 C17 103.04(11) . . ?
C10 C11 H11 107.4 . . ?
C12 C11 H11 107.4 . . ?
C17 C11 H11 107.4 . . ?
C15 C12 C13 100.30(12) . . ?
C15 C12 C11 107.00(11) . . ?
C13 C12 C11 98.98(11) . . ?
C15 C12 H12 116.1 . . ?
C13 C12 H12 116.1 . . ?
C11 C12 H12 116.1 . . ?
C12 C13 C14 94.12(11) . . ?
C12 C13 H13A 112.9 . . ?
C14 C13 H13A 112.9 . . ?
C12 C13 H13B 112.9 . . ?
C14 C13 H13B 112.9 . . ?
H13A C13 H13B 110.3 . . ?
C16 C14 C13 99.83(12) . . ?
C16 C14 C17 106.67(11) . . ?
C13 C14 C17 99.59(11) . . ?
C16 C14 H14 116.1 . . ?
C13 C14 H14 116.1 . . ?
C17 C14 H14 116.1 . . ?
C16 C15 C12 107.62(13) . . ?
C16 C15 H15 126.2 . . ?
C12 C15 H15 126.2 . . ?
C15 C16 C14 107.93(13) . . ?
C15 C16 H16 126.0 . . ?
C14 C16 H16 126.0 . . ?
N5 C17 C14 113.07(11) . . ?
N5 C17 C11 114.48(11) . . ?
C14 C17 C11 102.94(11) . . ?
N5 C17 H17 108.7 . . ?
C14 C17 H17 108.7 . . ?
C11 C17 H17 108.7 . . ?
N5 C18 N4 109.88(10) . . ?
N5 C18 C5 111.70(11) . . ?
N4 C18 C5 112.55(11) . . ?
N5 C18 H18 107.5 . . ?
N4 C18 H18 107.5 . . ?
C5 C18 H18 107.5 . . ?

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
C8 N1 N2 N3 -0.18(15) . . . . ?
C4 N1 N2 N3 179.54(12) . . . . ?
N1 N2 N3 C7 -0.14(15) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
Br1 C1 C2 C3 -178.57(10) . . . . ?
C1 C2 C3 C4 -1.6(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 N1 179.26(13) . . . . ?
C8 N1 C4 C3 -137.82(14) . . . . ?
N2 N1 C4 C3 42.50(19) . . . . ?
C8 N1 C4 C5 41.26(19) . . . . ?
N2 N1 C4 C5 -138.41(13) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
N1 C4 C5 C6 -177.75(12) . . . . ?
C3 C4 C5 C18 -170.56(13) . . . . ?
N1 C4 C5 C18 10.39(19) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
Br1 C1 C6 C5 -179.91(10) . . . . ?
C4 C5 C6 C1 -1.40(19) . . . . ?
C18 C5 C6 C1 170.58(12) . . . . ?
N2 N3 C7 C8 0.41(16) . . . . ?
N2 N1 C8 C7 0.41(15) . . . . ?
C4 N1 C8 C7 -179.29(12) . . . . ?
N2 N1 C8 C9 -179.20(11) . . . . ?
C4 N1 C8 C9 1.1(2) . . . . ?
N3 C7 C8 N1 -0.49(15) . . . . ?
N3 C7 C8 C9 179.04(14) . . . . ?
C10 N4 C9 C8 -113.14(14) . . . . ?
C18 N4 C9 C8 46.15(16) . . . . ?
N1 C8 C9 N4 -70.00(16) . . . . ?
C7 C8 C9 N4 110.53(17) . . . . ?
C9 N4 C10 O1 -18.3(2) . . . . ?
C18 N4 C10 O1 -177.24(13) . . . . ?
C9 N4 C10 C11 159.07(12) . . . . ?
C18 N4 C10 C11 0.12(19) . . . . ?
O1 C10 C11 C12 -43.13(19) . . . . ?
N4 C10 C11 C12 139.50(13) . . . . ?
O1 C10 C11 C17 -163.50(14) . . . . ?
N4 C10 C11 C17 19.13(18) . . . . ?
C10 C11 C12 C15 -61.91(16) . . . . ?
C17 C11 C12 C15 65.70(14) . . . . ?
C10 C11 C12 C13 -165.66(12) . . . . ?
C17 C11 C12 C13 -38.04(13) . . . . ?
C15 C12 C13 C14 -49.59(12) . . . . ?
C11 C12 C13 C14 59.65(12) . . . . ?
C12 C13 C14 C16 49.95(12) . . . . ?
C12 C13 C14 C17 -58.98(12) . . . . ?
C13 C12 C15 C16 32.32(14) . . . . ?
C11 C12 C15 C16 -70.47(15) . . . . ?
C12 C15 C16 C14 0.99(15) . . . . ?
C13 C14 C16 C15 -33.88(15) . . . . ?
C17 C14 C16 C15 69.32(15) . . . . ?
C18 N5 C17 C14 -163.77(11) . . . . ?
C18 N5 C17 C11 -46.29(15) . . . . ?
C16 C14 C17 N5 56.56(15) . . . . ?
C13 C14 C17 N5 159.93(11) . . . . ?
C16 C14 C17 C11 -67.49(14) . . . . ?
C13 C14 C17 C11 35.88(13) . . . . ?
C10 C11 C17 N5 4.53(17) . . . . ?
C12 C11 C17 N5 -121.78(12) . . . . ?
C10 C11 C17 C14 127.64(13) . . . . ?
C12 C11 C17 C14 1.33(13) . . . . ?
C17 N5 C18 N4 65.45(13) . . . . ?
C17 N5 C18 C5 -168.91(10) . . . . ?
C10 N4 C18 N5 -43.37(16) . . . . ?
C9 N4 C18 N5 158.05(11) . . . . ?
C10 N4 C18 C5 -168.53(12) . . . . ?
C9 N4 C18 C5 32.90(16) . . . . ?
C6 C5 C18 N5 -4.92(17) . . . . ?
C4 C5 C18 N5 166.68(12) . . . . ?
C6 C5 C18 N4 119.24(13) . . . . ?
C4 C5 C18 N4 -69.16(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9B Br1 0.99 2.84 3.5479(14) 129.4 2_645 yes
C18 H18 N3 1.00 2.47 3.3148(18) 141.6 5_656 yes

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2048905'
loop_
_audit_author_name
_audit_author_address
'Matti Haukka'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-02-04 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         'C17 H19 N5 O'
_chemical_formula_sum            'C17 H19 N5 O'
_chemical_formula_weight         309.37

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      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                   10.95560(10)
_cell_length_b                   8.17340(10)
_cell_length_c                   16.6676(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.8760(10)
_cell_angle_gamma                90
_cell_volume                     1474.62(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    14062
_cell_measurement_theta_min      4.0600
_cell_measurement_theta_max      76.7300

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.139
_exptl_absorpt_coefficient_mu    0.735
_shelx_estimated_absorpt_T_min   0.866
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   micro-source
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_reflns_number            20283
_diffrn_reflns_av_unetI/netI     0.0100
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.084
_diffrn_reflns_theta_max         76.900
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3120
_reflns_number_gt                3031
_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       
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2017)'
_computing_molecular_graphics    
'CrystaMaker X (CrystalMaker Software ltd., 2018)'
_computing_publication_material  'SHELXL-2017 (Sheldrick, 2017)'
_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)+(0.0460P)²+0.5634P] 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         3120
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
O1 O 0.05733(7) 0.16270(11) 0.57760(5) 0.0276(2) Uani 1 1 d . . . . .
N1 N 0.47787(7) 0.40470(10) 0.65315(5) 0.01553(18) Uani 1 1 d . . . . .
N2 N 0.53572(8) 0.52606(11) 0.69945(5) 0.0204(2) Uani 1 1 d . . . . .
N3 N 0.46363(8) 0.56470(12) 0.75274(6) 0.0237(2) Uani 1 1 d . . . . .
N4 N 0.24536(7) 0.24666(11) 0.55327(5) 0.01551(18) Uani 1 1 d . . . . .
N5 N 0.27787(7) 0.30195(11) 0.41715(5) 0.01586(18) Uani 1 1 d . . . . .
C1 C 0.46053(9) 0.27653(12) 0.52077(6) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.51810(9) 0.19150(12) 0.46425(6) 0.0177(2) Uani 1 1 d . . . . .
H2 H 0.470865 0.156782 0.414542 0.021 Uiso 1 1 calc R U . . .
C3 C 0.64378(9) 0.15716(13) 0.48000(6) 0.0201(2) Uani 1 1 d . . . . .
H3 H 0.681680 0.101054 0.440417 0.024 Uiso 1 1 calc R U . . .
C4 C 0.71492(9) 0.20382(13) 0.55294(6) 0.0196(2) Uani 1 1 d . . . . .
H4 H 0.800760 0.179821 0.563124 0.023 Uiso 1 1 calc R U . . .
C5 C 0.65927(9) 0.28561(12) 0.61053(6) 0.0178(2) Uani 1 1 d . . . . .
H5A H 0.706075 0.316075 0.661119 0.021 Uiso 1 1 calc R U . . .
C6 C 0.53404(9) 0.32251(12) 0.59332(6) 0.0153(2) Uani 1 1 d . . . . .
C7 C 0.36136(9) 0.46818(13) 0.74046(6) 0.0204(2) Uani 1 1 d . . . . .
H7 H 0.295386 0.471630 0.771313 0.024 Uiso 1 1 calc R U . . .
C8 C 0.36855(9) 0.36546(12) 0.67670(6) 0.0161(2) Uani 1 1 d . . . . .
C9 C 0.29443(9) 0.22434(13) 0.63938(6) 0.0171(2) Uani 1 1 d . . . . .
H9A H 0.346847 0.125090 0.645435 0.021 Uiso 1 1 calc R U . . .
H9B H 0.224607 0.205636 0.669547 0.021 Uiso 1 1 calc R U . . .
C10 C 0.12311(9) 0.21137(13) 0.52910(6) 0.0175(2) Uani 1 1 d . . . . .
C11 C 0.07487(9) 0.22650(13) 0.43939(6) 0.0169(2) Uani 1 1 d . . . . .
H11 H 0.087896 0.117800 0.414507 0.020 Uiso 1 1 calc R U . . .
C12 C -0.06351(9) 0.26099(15) 0.42205(6) 0.0222(2) Uani 1 1 d . . . . .
H12A H -0.108735 0.175691 0.447716 0.027 Uiso 1 1 calc R U . . .
H12B H -0.081090 0.368185 0.445455 0.027 Uiso 1 1 calc R U . . .
C13 C -0.10703(9) 0.26244(15) 0.33063(6) 0.0244(2) Uani 1 1 d . . . . .
H13A H -0.195922 0.290686 0.319792 0.029 Uiso 1 1 calc R U . . .
H13B H -0.096892 0.151805 0.308388 0.029 Uiso 1 1 calc R U . . .
C14 C -0.03398(10) 0.38602(15) 0.28787(7) 0.0250(2) Uani 1 1 d . . . . .
H14A H -0.050963 0.498084 0.305798 0.030 Uiso 1 1 calc R U . . .
H14B H -0.060942 0.379576 0.228464 0.030 Uiso 1 1 calc R U . . .
C15 C 0.10485(9) 0.35154(14) 0.30716(6) 0.0200(2) Uani 1 1 d . . . . .
H15A H 0.122887 0.244163 0.284135 0.024 Uiso 1 1 calc R U . . .
H15B H 0.150586 0.436423 0.281582 0.024 Uiso 1 1 calc R U . . .
C16 C 0.14820(9) 0.35065(12) 0.39832(6) 0.0160(2) Uani 1 1 d . . . . .
H16 H 0.137290 0.462081 0.420953 0.019 Uiso 1 1 calc R U . . .
C17 C 0.32570(8) 0.33086(12) 0.50181(6) 0.0147(2) Uani 1 1 d . . . . .
H17 H 0.322145 0.451121 0.512234 0.018 Uiso 1 1 calc R U . . .
H5 H 0.3252(12) 0.3576(17) 0.3870(8) 0.021(3) 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
O1 C10 1.2291(13) . yes
N1 N2 1.3529(12) . yes
N1 C8 1.3551(12) . yes
N1 C6 1.4190(12) . yes
N2 N3 1.3150(13) . yes
N3 C7 1.3596(14) . yes
N4 C10 1.3686(12) . yes
N4 C9 1.4643(12) . yes
N4 C17 1.4888(12) . yes
N5 C17 1.4468(12) . yes
N5 C16 1.4621(12) . yes
N5 H5 0.899(14) . ?
C1 C6 1.3970(13) . ?
C1 C2 1.3970(13) . ?
C1 C17 1.5281(13) . ?
C2 C3 1.3899(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3923(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3859(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3907(14) . ?
C5 H5A 0.9500 . ?
C7 C8 1.3661(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.4903(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5121(13) . ?
C11 C16 1.5210(13) . ?
C11 C12 1.5251(13) . ?
C11 H11 1.0000 . ?
C12 C13 1.5248(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5313(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5313(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5203(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16 1.0000 . ?
C17 H17 1.0000 . ?

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
N2 N1 C8 111.44(8) . . ?
N2 N1 C6 122.15(8) . . ?
C8 N1 C6 126.15(8) . . ?
N3 N2 N1 106.50(8) . . ?
N2 N3 C7 109.01(8) . . ?
C10 N4 C9 117.19(8) . . ?
C10 N4 C17 124.51(8) . . ?
C9 N4 C17 117.52(8) . . ?
C17 N5 C16 111.02(7) . . ?
C17 N5 H5 108.0(9) . . ?
C16 N5 H5 111.5(8) . . ?
C6 C1 C2 117.23(9) . . ?
C6 C1 C17 120.71(8) . . ?
C2 C1 C17 121.85(9) . . ?
C3 C2 C1 120.68(9) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.95(9) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.35(9) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.15(9) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C5 C6 C1 122.60(9) . . ?
C5 C6 N1 118.60(9) . . ?
C1 C6 N1 118.75(9) . . ?
N3 C7 C8 109.19(9) . . ?
N3 C7 H7 125.4 . . ?
C8 C7 H7 125.4 . . ?
N1 C8 C7 103.86(9) . . ?
N1 C8 C9 120.75(9) . . ?
C7 C8 C9 135.01(9) . . ?
N4 C9 C8 114.00(8) . . ?
N4 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
N4 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
O1 C10 N4 121.41(9) . . ?
O1 C10 C11 121.73(9) . . ?
N4 C10 C11 116.79(8) . . ?
C10 C11 C16 111.80(8) . . ?
C10 C11 C12 112.83(8) . . ?
C16 C11 C12 111.71(8) . . ?
C10 C11 H11 106.7 . . ?
C16 C11 H11 106.7 . . ?
C12 C11 H11 106.7 . . ?
C13 C12 C11 109.83(8) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 111.40(9) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.75(9) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.96(8) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N5 C16 C15 111.06(8) . . ?
N5 C16 C11 106.55(8) . . ?
C15 C16 C11 110.35(8) . . ?
N5 C16 H16 109.6 . . ?
C15 C16 H16 109.6 . . ?
C11 C16 H16 109.6 . . ?
N5 C17 N4 109.21(8) . . ?
N5 C17 C1 110.32(8) . . ?
N4 C17 C1 112.65(8) . . ?
N5 C17 H17 108.2 . . ?
N4 C17 H17 108.2 . . ?
C1 C17 H17 108.2 . . ?

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
C8 N1 N2 N3 0.03(11) . . . . ?
C6 N1 N2 N3 -174.49(9) . . . . ?
N1 N2 N3 C7 0.24(12) . . . . ?
C6 C1 C2 C3 -0.92(14) . . . . ?
C17 C1 C2 C3 173.83(9) . . . . ?
C1 C2 C3 C4 1.20(16) . . . . ?
C2 C3 C4 C5 0.02(16) . . . . ?
C3 C4 C5 C6 -1.46(15) . . . . ?
C4 C5 C6 C1 1.76(15) . . . . ?
C4 C5 C6 N1 179.32(9) . . . . ?
C2 C1 C6 C5 -0.56(14) . . . . ?
C17 C1 C6 C5 -175.37(9) . . . . ?
C2 C1 C6 N1 -178.12(8) . . . . ?
C17 C1 C6 N1 7.08(14) . . . . ?
N2 N1 C6 C5 39.47(13) . . . . ?
C8 N1 C6 C5 -134.21(10) . . . . ?
N2 N1 C6 C1 -142.87(9) . . . . ?
C8 N1 C6 C1 43.45(14) . . . . ?
N2 N3 C7 C8 -0.43(12) . . . . ?
N2 N1 C8 C7 -0.28(11) . . . . ?
C6 N1 C8 C7 173.97(9) . . . . ?
N2 N1 C8 C9 -174.21(8) . . . . ?
C6 N1 C8 C9 0.05(15) . . . . ?
N3 C7 C8 N1 0.43(11) . . . . ?
N3 C7 C8 C9 173.03(11) . . . . ?
C10 N4 C9 C8 -132.19(9) . . . . ?
C17 N4 C9 C8 38.10(12) . . . . ?
N1 C8 C9 N4 -66.41(12) . . . . ?
C7 C8 C9 N4 121.95(12) . . . . ?
C9 N4 C10 O1 -0.13(15) . . . . ?
C17 N4 C10 O1 -169.66(10) . . . . ?
C9 N4 C10 C11 -176.97(8) . . . . ?
C17 N4 C10 C11 13.49(14) . . . . ?
O1 C10 C11 C16 155.85(10) . . . . ?
N4 C10 C11 C16 -27.32(12) . . . . ?
O1 C10 C11 C12 28.92(14) . . . . ?
N4 C10 C11 C12 -154.24(9) . . . . ?
C10 C11 C12 C13 -175.95(9) . . . . ?
C16 C11 C12 C13 57.08(12) . . . . ?
C11 C12 C13 C14 -56.04(12) . . . . ?
C12 C13 C14 C15 55.92(12) . . . . ?
C13 C14 C15 C16 -55.87(12) . . . . ?
C17 N5 C16 C15 169.06(8) . . . . ?
C17 N5 C16 C11 -70.73(10) . . . . ?
C14 C15 C16 N5 174.41(8) . . . . ?
C14 C15 C16 C11 56.47(11) . . . . ?
C10 C11 C16 N5 54.23(10) . . . . ?
C12 C11 C16 N5 -178.24(8) . . . . ?
C10 C11 C16 C15 174.90(8) . . . . ?
C12 C11 C16 C15 -57.58(11) . . . . ?
C16 N5 C17 N4 54.68(10) . . . . ?
C16 N5 C17 C1 179.00(8) . . . . ?
C10 N4 C17 N5 -26.13(13) . . . . ?
C9 N4 C17 N5 164.37(8) . . . . ?
C10 N4 C17 C1 -149.08(9) . . . . ?
C9 N4 C17 C1 41.42(11) . . . . ?
C6 C1 C17 N5 166.64(8) . . . . ?
C2 C1 C17 N5 -7.93(13) . . . . ?
C6 C1 C17 N4 -71.04(11) . . . . ?
C2 C1 C17 N4 114.40(10) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044

