# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

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

data_dqp01_a
_database_code_depnum_ccdc_archive 'CCDC 1962959'
_audit_update_record             
;
2019-11-01 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N5 O2'
_chemical_formula_sum            'C23 H17 N5 O2'
_chemical_formula_weight         395.42

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.158(2)
_cell_length_b                   11.434(2)
_cell_length_c                   15.708(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.925(4)
_cell_angle_gamma                90.00
_cell_volume                     1989.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2298
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      24.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9906
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3518
_reflns_number_gt                1999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.2000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3518
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.1017
_refine_ls_wR_factor_ref         0.3298
_refine_ls_wR_factor_gt          0.2944
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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 0.6360(3) 0.4167(2) 0.63082(19) 0.0603(8) Uani 1 1 d . . .
C17 C 0.7490(3) 0.4550(3) 0.6749(2) 0.0592(9) Uani 1 1 d . . .
C1 C 0.5267(3) 0.4271(3) 0.6612(2) 0.0607(10) Uani 1 1 d . . .
N2 N 0.3191(4) 0.3519(4) 0.6123(3) 0.0915(12) Uani 1 1 d . . .
C5 C 0.5122(3) 0.4879(3) 0.7419(2) 0.0609(10) Uani 1 1 d . . .
O1 O 0.2795(3) 0.3784(4) 0.6735(3) 0.1166(13) Uani 1 1 d . . .
C22 C 0.8397(3) 0.3746(3) 0.6988(3) 0.0687(11) Uani 1 1 d . . .
H22 H 0.8279 0.2960 0.6849 0.082 Uiso 1 1 calc R . .
C11 C 0.7209(4) 0.3292(3) 0.5012(2) 0.0664(10) Uani 1 1 d . . .
C18 C 0.7674(3) 0.5712(3) 0.6969(3) 0.0669(11) Uani 1 1 d . . .
H18 H 0.7072 0.6259 0.6810 0.080 Uiso 1 1 calc R . .
C4 C 0.6217(4) 0.3550(3) 0.5539(2) 0.0700(11) Uani 1 1 d . . .
C2 C 0.4422(4) 0.3713(4) 0.6022(3) 0.0716(11) Uani 1 1 d . . .
C19 C 0.8744(4) 0.6060(4) 0.7422(3) 0.0821(13) Uani 1 1 d . . .
H19 H 0.8851 0.6842 0.7574 0.099 Uiso 1 1 calc R . .
C6 C 0.5796(4) 0.4611(4) 0.8178(3) 0.0774(12) Uani 1 1 d . . .
H6 H 0.6362 0.4013 0.8198 0.093 Uiso 1 1 calc R . .
C10 C 0.4286(4) 0.5793(3) 0.7402(3) 0.0763(12) Uani 1 1 d . . .
H10 H 0.3826 0.5990 0.6889 0.092 Uiso 1 1 calc R . .
C21 C 0.9466(4) 0.4105(4) 0.7428(3) 0.0810(12) Uani 1 1 d . . .
H21 H 1.0069 0.3556 0.7578 0.097 Uiso 1 1 calc R . .
C20 C 0.9678(4) 0.5261(4) 0.7659(3) 0.0785(12) Uani 1 1 d . . .
C3 C 0.5026(4) 0.3267(4) 0.5368(3) 0.0791(12) Uani 1 1 d . . .
O2 O 0.2577(4) 0.3031(5) 0.5523(3) 0.1442(17) Uani 1 1 d . . .
N3 N 0.4533(5) 0.2691(5) 0.4555(3) 0.1190(16) Uani 1 1 d . . .
C9 C 0.4141(5) 0.6391(4) 0.8123(4) 0.0944(15) Uani 1 1 d . . .
H9 H 0.3577 0.6993 0.8102 0.113 Uiso 1 1 calc R . .
C8 C 0.4808(6) 0.6126(5) 0.8875(4) 0.1014(17) Uani 1 1 d . . .
H8 H 0.4706 0.6552 0.9366 0.122 Uiso 1 1 calc R . .
C7 C 0.5643(5) 0.5223(5) 0.8919(3) 0.0920(14) Uani 1 1 d . . .
H7 H 0.6093 0.5031 0.9437 0.110 Uiso 1 1 calc R . .
C12 C 0.7250(5) 0.2211(5) 0.4617(3) 0.0950(15) Uani 1 1 d . . .
H12 H 0.6693 0.1633 0.4708 0.114 Uiso 1 1 calc R . .
C16 C 0.8007(5) 0.4128(5) 0.4844(3) 0.0952(15) Uani 1 1 d . . .
H16 H 0.7960 0.4864 0.5089 0.114 Uiso 1 1 calc R . .
C13 C 0.8139(5) 0.1997(5) 0.4079(4) 0.1072(16) Uani 1 1 d . . .
H13 H 0.8167 0.1274 0.3810 0.129 Uiso 1 1 calc R . .
C14 C 0.8949(5) 0.2821(6) 0.3948(4) 0.1120(18) Uani 1 1 d . . .
H14 H 0.9556 0.2660 0.3608 0.134 Uiso 1 1 calc R . .
C15 C 0.8881(5) 0.3920(6) 0.4322(4) 0.1104(18) Uani 1 1 d . . .
H15 H 0.9424 0.4505 0.4218 0.132 Uiso 1 1 calc R . .
C23 C 1.0855(5) 0.5621(5) 0.8136(4) 0.124(2) Uani 1 1 d . . .
H23A H 1.0741 0.5829 0.8713 0.186 Uiso 1 1 calc R . .
H23B H 1.1166 0.6283 0.7857 0.186 Uiso 1 1 calc R . .
H23C H 1.1418 0.4984 0.8146 0.186 Uiso 1 1 calc R . .
N4 N 0.3977(7) 0.1849(8) 0.4586(3) 0.157(3) Uani 1 1 d . . .
N5 N 0.3419(12) 0.0985(11) 0.4472(6) 0.267(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.367(4) . ?
N1 C4 1.392(5) . ?
N1 C17 1.433(5) . ?
C17 C18 1.382(5) . ?
C17 C22 1.385(5) . ?
C1 C2 1.394(5) . ?
C1 C5 1.471(5) . ?
N2 O1 1.146(5) . ?
N2 O2 1.231(5) . ?
N2 C2 1.420(6) . ?
C5 C6 1.366(5) . ?
C5 C10 1.398(5) . ?
C22 C21 1.368(6) . ?
C22 H22 0.9300 . ?
C11 C16 1.355(6) . ?
C11 C12 1.387(6) . ?
C11 C4 1.489(6) . ?
C18 C19 1.372(6) . ?
C18 H18 0.9300 . ?
C4 C3 1.362(6) . ?
C2 C3 1.392(6) . ?
C19 C20 1.402(6) . ?
C19 H19 0.9300 . ?
C6 C7 1.385(6) . ?
C6 H6 0.9300 . ?
C10 C9 1.348(7) . ?
C10 H10 0.9300 . ?
C21 C20 1.383(6) . ?
C21 H21 0.9300 . ?
C20 C23 1.490(6) . ?
C3 N3 1.482(7) . ?
N3 N4 1.150(8) . ?
C9 C8 1.353(7) . ?
C9 H9 0.9300 . ?
C8 C7 1.387(8) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C12 C13 1.399(7) . ?
C12 H12 0.9300 . ?
C16 C15 1.368(7) . ?
C16 H16 0.9300 . ?
C13 C14 1.339(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N4 N5 1.169(9) . ?

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
C1 N1 C4 109.5(3) . . ?
C1 N1 C17 125.1(3) . . ?
C4 N1 C17 125.2(3) . . ?
C18 C17 C22 119.3(4) . . ?
C18 C17 N1 120.7(3) . . ?
C22 C17 N1 120.0(3) . . ?
N1 C1 C2 106.7(3) . . ?
N1 C1 C5 122.5(3) . . ?
C2 C1 C5 130.8(3) . . ?
O1 N2 O2 121.8(5) . . ?
O1 N2 C2 121.9(5) . . ?
O2 N2 C2 116.2(5) . . ?
C6 C5 C10 118.6(4) . . ?
C6 C5 C1 122.7(3) . . ?
C10 C5 C1 118.6(4) . . ?
C21 C22 C17 120.1(4) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C16 C11 C12 118.9(4) . . ?
C16 C11 C4 121.3(4) . . ?
C12 C11 C4 119.5(4) . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C3 C4 N1 107.3(4) . . ?
C3 C4 C11 128.0(4) . . ?
N1 C4 C11 124.6(4) . . ?
C3 C2 C1 108.1(4) . . ?
C3 C2 N2 125.9(4) . . ?
C1 C2 N2 125.6(4) . . ?
C18 C19 C20 121.4(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C5 C6 C7 120.6(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C9 C10 C5 120.7(5) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C22 C21 C20 122.1(4) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C20 C19 117.1(4) . . ?
C21 C20 C23 120.6(4) . . ?
C19 C20 C23 122.4(4) . . ?
C4 C3 C2 108.4(4) . . ?
C4 C3 N3 121.8(4) . . ?
C2 C3 N3 129.5(4) . . ?
N4 N3 C3 118.9(5) . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C8 C7 120.3(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C6 C7 C8 119.0(5) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C11 C12 C13 119.4(5) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C11 C16 C15 121.8(5) . . ?
C11 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C14 C13 C12 120.7(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.8(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.3(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 N4 N5 168.8(8) . . ?

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
C1 N1 C17 C18 -59.9(5) . . . . ?
C4 N1 C17 C18 125.6(4) . . . . ?
C1 N1 C17 C22 117.6(4) . . . . ?
C4 N1 C17 C22 -56.9(5) . . . . ?
C4 N1 C1 C2 -0.3(4) . . . . ?
C17 N1 C1 C2 -175.5(3) . . . . ?
C4 N1 C1 C5 179.9(3) . . . . ?
C17 N1 C1 C5 4.6(5) . . . . ?
N1 C1 C5 C6 -53.3(5) . . . . ?
C2 C1 C5 C6 126.8(4) . . . . ?
N1 C1 C5 C10 124.7(4) . . . . ?
C2 C1 C5 C10 -55.2(5) . . . . ?
C18 C17 C22 C21 -0.7(6) . . . . ?
N1 C17 C22 C21 -178.3(3) . . . . ?
C22 C17 C18 C19 -0.2(6) . . . . ?
N1 C17 C18 C19 177.3(3) . . . . ?
C1 N1 C4 C3 -0.1(4) . . . . ?
C17 N1 C4 C3 175.1(3) . . . . ?
C1 N1 C4 C11 178.6(3) . . . . ?
C17 N1 C4 C11 -6.2(5) . . . . ?
C16 C11 C4 C3 132.8(5) . . . . ?
C12 C11 C4 C3 -40.8(6) . . . . ?
C16 C11 C4 N1 -45.6(6) . . . . ?
C12 C11 C4 N1 140.8(4) . . . . ?
N1 C1 C2 C3 0.6(4) . . . . ?
C5 C1 C2 C3 -179.6(4) . . . . ?
N1 C1 C2 N2 173.9(4) . . . . ?
C5 C1 C2 N2 -6.2(6) . . . . ?
O1 N2 C2 C3 169.5(5) . . . . ?
O2 N2 C2 C3 -9.2(7) . . . . ?
O1 N2 C2 C1 -2.6(7) . . . . ?
O2 N2 C2 C1 178.6(4) . . . . ?
C17 C18 C19 C20 1.1(6) . . . . ?
C10 C5 C6 C7 0.8(6) . . . . ?
C1 C5 C6 C7 178.8(4) . . . . ?
C6 C5 C10 C9 -0.5(6) . . . . ?
C1 C5 C10 C9 -178.6(3) . . . . ?
C17 C22 C21 C20 0.8(6) . . . . ?
C22 C21 C20 C19 0.1(7) . . . . ?
C22 C21 C20 C23 -179.8(5) . . . . ?
C18 C19 C20 C21 -1.0(6) . . . . ?
C18 C19 C20 C23 178.8(5) . . . . ?
N1 C4 C3 C2 0.5(5) . . . . ?
C11 C4 C3 C2 -178.2(4) . . . . ?
N1 C4 C3 N3 174.7(4) . . . . ?
C11 C4 C3 N3 -4.0(7) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
N2 C2 C3 C4 -174.0(4) . . . . ?
C1 C2 C3 N3 -174.2(4) . . . . ?
N2 C2 C3 N3 12.4(8) . . . . ?
C4 C3 N3 N4 127.6(7) . . . . ?
C2 C3 N3 N4 -59.6(9) . . . . ?
C5 C10 C9 C8 0.5(6) . . . . ?
C10 C9 C8 C7 -0.8(7) . . . . ?
C5 C6 C7 C8 -1.0(7) . . . . ?
C9 C8 C7 C6 1.0(7) . . . . ?
C16 C11 C12 C13 2.2(7) . . . . ?
C4 C11 C12 C13 176.0(4) . . . . ?
C12 C11 C16 C15 -2.7(7) . . . . ?
C4 C11 C16 C15 -176.3(5) . . . . ?
C11 C12 C13 C14 0.4(8) . . . . ?
C12 C13 C14 C15 -2.6(9) . . . . ?
C11 C16 C15 C14 0.5(8) . . . . ?
C13 C14 C15 C16 2.2(9) . . . . ?
C3 N3 N4 N5 -173(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.077
