# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ljj-158
_database_code_depnum_ccdc_archive 'CCDC 1546763'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N5 O'
_chemical_formula_sum            'C20 H17 N5 O'
_chemical_formula_weight         343.39

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.2708(5)
_cell_length_b                   19.5714(12)
_cell_length_c                   10.5066(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.832(2)
_cell_angle_gamma                90.00
_cell_volume                     1651.40(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8242
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14077
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0674
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3237
_reflns_number_gt                1936
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0591P)²+1.1424P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0100(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3237
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
C1 C 0.0195(4) -0.11448(15) 0.4224(3) 0.0376(7) Uani 1 1 d . . .
C2 C 0.0389(3) -0.05430(15) 0.2409(3) 0.0386(7) Uani 1 1 d . . .
H2 H 0.0108 -0.0466 0.1509 0.046 Uiso 1 1 calc R . .
C3 C 0.2470(3) 0.04415(14) 0.2962(3) 0.0328(7) Uani 1 1 d . . .
C4 C 0.3272(3) 0.06565(14) 0.4207(3) 0.0323(7) Uani 1 1 d . . .
C5 C 0.1828(3) -0.02081(14) 0.4552(3) 0.0339(7) Uani 1 1 d . . .
C6 C 0.2417(4) 0.06340(14) 0.1608(3) 0.0377(7) Uani 1 1 d . . .
C7 C 0.3972(4) 0.07946(14) 0.1188(3) 0.0357(7) Uani 1 1 d . . .
C8 C 0.3833(4) 0.10506(15) -0.0069(3) 0.0430(8) Uani 1 1 d . . .
H8 H 0.2790 0.1155 -0.0598 0.052 Uiso 1 1 calc R . .
C9 C 0.5247(5) 0.11488(17) -0.0527(3) 0.0557(9) Uani 1 1 d . . .
H9 H 0.5153 0.1320 -0.1367 0.067 Uiso 1 1 calc R . .
C10 C 0.6795(5) 0.09948(18) 0.0247(4) 0.0582(10) Uani 1 1 d . . .
H10 H 0.7741 0.1064 -0.0069 0.070 Uiso 1 1 calc R . .
C11 C 0.6941(4) 0.07397(17) 0.1480(4) 0.0526(9) Uani 1 1 d . . .
H11 H 0.7988 0.0636 0.2000 0.063 Uiso 1 1 calc R . .
C12 C 0.5543(4) 0.06346(16) 0.1959(3) 0.0432(8) Uani 1 1 d . . .
H12 H 0.5652 0.0457 0.2796 0.052 Uiso 1 1 calc R . .
C13 C 0.4328(3) 0.12632(14) 0.4619(3) 0.0343(7) Uani 1 1 d . . .
C14 C 0.4266(4) 0.18381(15) 0.3831(3) 0.0425(8) Uani 1 1 d . . .
H14 H 0.3579 0.1837 0.2989 0.051 Uiso 1 1 calc R . .
C15 C 0.5204(4) 0.24107(17) 0.4275(3) 0.0512(9) Uani 1 1 d . . .
H15 H 0.5152 0.2790 0.3735 0.061 Uiso 1 1 calc R . .
C16 C 0.6219(4) 0.24180(17) 0.5523(3) 0.0528(9) Uani 1 1 d . . .
H16 H 0.6854 0.2803 0.5823 0.063 Uiso 1 1 calc R . .
C17 C 0.6297(4) 0.18587(17) 0.6327(3) 0.0466(8) Uani 1 1 d . . .
H17 H 0.6981 0.1866 0.7170 0.056 Uiso 1 1 calc R . .
C18 C 0.5357(4) 0.12837(15) 0.5879(3) 0.0392(7) Uani 1 1 d . . .
H18 H 0.5413 0.0907 0.6426 0.047 Uiso 1 1 calc R . .
C19 C 0.0164(5) -0.18824(17) 0.6065(3) 0.0562(9) Uani 1 1 d . . .
H19A H 0.1359 -0.1876 0.6311 0.084 Uiso 1 1 calc R . .
H19B H -0.0228 -0.2330 0.6217 0.084 Uiso 1 1 calc R . .
H19C H -0.0264 -0.1554 0.6578 0.084 Uiso 1 1 calc R . .
C20 C -0.1509(4) -0.21881(17) 0.3827(3) 0.0533(9) Uani 1 1 d . . .
H20A H -0.2064 -0.1958 0.3036 0.080 Uiso 1 1 calc R . .
H20B H -0.2321 -0.2358 0.4266 0.080 Uiso 1 1 calc R . .
H20C H -0.0871 -0.2563 0.3616 0.080 Uiso 1 1 calc R . .
N1 N -0.0407(3) -0.17123(12) 0.4680(3) 0.0440(7) Uani 1 1 d . . .
N2 N -0.0262(3) -0.10595(12) 0.2878(2) 0.0407(6) Uani 1 1 d . . .
N3 N 0.1473(3) -0.01098(11) 0.3197(2) 0.0339(6) Uani 1 1 d . . .
N4 N 0.2883(3) 0.02582(12) 0.5176(2) 0.0348(6) Uani 1 1 d . . .
N5 N 0.1167(3) -0.07304(12) 0.5079(2) 0.0363(6) Uani 1 1 d . . .
O1 O 0.1072(3) 0.06146(12) 0.0795(2) 0.0545(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
C1 N5 1.329(4) . ?
C1 N1 1.351(4) . ?
C1 N2 1.383(4) . ?
C2 N2 1.297(4) . ?
C2 N3 1.362(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 N3 1.415(3) . ?
C3 C6 1.462(4) . ?
C4 N4 1.380(3) . ?
C4 C13 1.476(4) . ?
C5 N4 1.323(3) . ?
C5 N5 1.340(3) . ?
C5 N3 1.396(3) . ?
C6 O1 1.230(3) . ?
C6 C7 1.490(4) . ?
C7 C8 1.391(4) . ?
C7 C12 1.393(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.391(4) . ?
C13 C18 1.393(4) . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N1 1.456(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N1 1.453(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
N5 C1 N1 118.4(3) . . ?
N5 C1 N2 126.2(3) . . ?
N1 C1 N2 115.4(3) . . ?
N2 C2 N3 121.8(3) . . ?
N2 C2 H2 119.1 . . ?
N3 C2 H2 119.1 . . ?
C4 C3 N3 103.6(2) . . ?
C4 C3 C6 137.6(3) . . ?
N3 C3 C6 118.9(2) . . ?
N4 C4 C3 112.5(2) . . ?
N4 C4 C13 117.7(2) . . ?
C3 C4 C13 129.6(3) . . ?
N4 C5 N5 127.3(3) . . ?
N4 C5 N3 111.3(2) . . ?
N5 C5 N3 121.3(3) . . ?
O1 C6 C3 118.6(3) . . ?
O1 C6 C7 120.2(3) . . ?
C3 C6 C7 121.0(3) . . ?
C8 C7 C12 119.2(3) . . ?
C8 C7 C6 118.4(3) . . ?
C12 C7 C6 122.1(3) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C14 C13 C18 118.0(3) . . ?
C14 C13 C4 122.8(3) . . ?
C18 C13 C4 119.1(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C20 122.5(3) . . ?
C1 N1 C19 118.9(3) . . ?
C20 N1 C19 118.4(3) . . ?
C2 N2 C1 116.5(3) . . ?
C2 N3 C5 118.8(2) . . ?
C2 N3 C3 134.0(2) . . ?
C5 N3 C3 107.1(2) . . ?
C5 N4 C4 105.4(2) . . ?
C1 N5 C5 115.2(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
N3 C3 C4 N4 2.4(3) . . . . ?
C6 C3 C4 N4 -177.9(3) . . . . ?
N3 C3 C4 C13 -172.0(3) . . . . ?
C6 C3 C4 C13 7.7(5) . . . . ?
C4 C3 C6 O1 -141.2(4) . . . . ?
N3 C3 C6 O1 38.5(4) . . . . ?
C4 C3 C6 C7 43.9(5) . . . . ?
N3 C3 C6 C7 -136.5(3) . . . . ?
O1 C6 C7 C8 12.5(4) . . . . ?
C3 C6 C7 C8 -172.6(3) . . . . ?
O1 C6 C7 C12 -161.1(3) . . . . ?
C3 C6 C7 C12 13.8(4) . . . . ?
C12 C7 C8 C9 -0.6(4) . . . . ?
C6 C7 C8 C9 -174.4(3) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C7 -0.5(5) . . . . ?
C8 C7 C12 C11 0.9(4) . . . . ?
C6 C7 C12 C11 174.4(3) . . . . ?
N4 C4 C13 C14 -152.9(3) . . . . ?
C3 C4 C13 C14 21.2(5) . . . . ?
N4 C4 C13 C18 22.9(4) . . . . ?
C3 C4 C13 C18 -163.0(3) . . . . ?
C18 C13 C14 C15 0.6(4) . . . . ?
C4 C13 C14 C15 176.4(3) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C13 0.1(5) . . . . ?
C14 C13 C18 C17 -0.5(4) . . . . ?
C4 C13 C18 C17 -176.4(3) . . . . ?
N5 C1 N1 C20 178.5(3) . . . . ?
N2 C1 N1 C20 -2.2(4) . . . . ?
N5 C1 N1 C19 -6.1(4) . . . . ?
N2 C1 N1 C19 173.1(3) . . . . ?
N3 C2 N2 C1 0.4(4) . . . . ?
N5 C1 N2 C2 3.6(4) . . . . ?
N1 C1 N2 C2 -175.6(3) . . . . ?
N2 C2 N3 C5 -3.1(4) . . . . ?
N2 C2 N3 C3 173.2(3) . . . . ?
N4 C5 N3 C2 -179.2(2) . . . . ?
N5 C5 N3 C2 2.2(4) . . . . ?
N4 C5 N3 C3 3.6(3) . . . . ?
N5 C5 N3 C3 -174.9(2) . . . . ?
C4 C3 N3 C2 180.0(3) . . . . ?
C6 C3 N3 C2 0.2(4) . . . . ?
C4 C3 N3 C5 -3.5(3) . . . . ?
C6 C3 N3 C5 176.8(2) . . . . ?
N5 C5 N4 C4 176.4(3) . . . . ?
N3 C5 N4 C4 -2.1(3) . . . . ?
C3 C4 N4 C5 -0.3(3) . . . . ?
C13 C4 N4 C5 174.8(2) . . . . ?
N1 C1 N5 C5 174.8(2) . . . . ?
N2 C1 N5 C5 -4.3(4) . . . . ?
N4 C5 N5 C1 -177.0(3) . . . . ?
N3 C5 N5 C1 1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.057
