# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_exp_1074
_database_code_depnum_ccdc_archive 'CCDC 1505314'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2017-01-22 downloaded from the CCDC.
;
_audit_creation_date             2016-09-16
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H18 N4 O'
_chemical_formula_sum            'C19 H18 N4 O'
_chemical_formula_weight         318.37
_chemical_melting_point          ?
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   11.5790(8)
_cell_length_b                   9.4791(5)
_cell_length_c                   30.0335(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3296.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1735
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.9670
_cell_measurement_theta_min      2.8630
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            11172
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.78
_diffrn_reflns_theta_min         2.71
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.8913
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   16.00   1.0000  159.8200
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega   12.00   64.00   1.0000  159.8200
omega____ theta____ kappa____ phi______ frames
    -       23.2924   57.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   69.00   1.0000  159.8200
omega____ theta____ kappa____ phi______ frames
    -       23.2924   57.0000  120.0000 67
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0241768000
_diffrn_orient_matrix_UB_12      0.0186823000
_diffrn_orient_matrix_UB_13      -0.0208752000
_diffrn_orient_matrix_UB_21      -0.0525080000
_diffrn_orient_matrix_UB_22      -0.0185469000
_diffrn_orient_matrix_UB_23      -0.0106835000
_diffrn_orient_matrix_UB_31      -0.0203645000
_diffrn_orient_matrix_UB_32      0.0700258000
_diffrn_orient_matrix_UB_33      0.0027441000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2401
_reflns_number_total             4570
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0047(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1607
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O1 O 0.70826(12) 0.09380(19) 0.62864(5) 0.0948(5) Uani 1 1 d . . .
N1 N 0.18423(13) 0.27535(14) 0.59283(5) 0.0593(4) Uani 1 1 d . . .
N2 N 0.12216(13) 0.21717(15) 0.62626(5) 0.0614(4) Uani 1 1 d . . .
N3 N 0.46716(12) 0.13470(14) 0.62064(4) 0.0567(4) Uani 1 1 d . . .
N4 N 0.28630(12) 0.08379(13) 0.64783(4) 0.0521(3) Uani 1 1 d . . .
C3 C 0.17371(14) 0.11583(16) 0.64953(5) 0.0492(4) Uani 1 1 d . . .
C5 C 0.35089(14) 0.15394(15) 0.61858(5) 0.0483(4) Uani 1 1 d . . .
C6 C 0.29364(14) 0.24067(15) 0.58652(5) 0.0499(4) Uani 1 1 d . . .
C7 C 0.34262(15) 0.28971(16) 0.54331(5) 0.0533(4) Uani 1 1 d . . .
C8 C 0.31108(17) 0.41990(18) 0.52628(6) 0.0648(5) Uani 1 1 d . . .
H8 H 0.2636 0.4791 0.5429 0.078 Uiso 1 1 calc R . .
C9 C 0.3495(2) 0.4626(2) 0.48493(7) 0.0793(6) Uani 1 1 d . . .
H9 H 0.3277 0.5502 0.4738 0.095 Uiso 1 1 calc R . .
C10 C 0.4200(2) 0.3761(3) 0.46021(7) 0.0807(6) Uani 1 1 d . . .
H10 H 0.4458 0.4050 0.4323 0.097 Uiso 1 1 calc R . .
C11 C 0.45225(18) 0.2467(2) 0.47670(6) 0.0740(5) Uani 1 1 d . . .
H11 H 0.5000 0.1882 0.4600 0.089 Uiso 1 1 calc R . .
C12 C 0.41384(16) 0.20341(19) 0.51802(6) 0.0622(5) Uani 1 1 d . . .
H12 H 0.4359 0.1157 0.5290 0.075 Uiso 1 1 calc R . .
C13 C 0.10062(15) 0.03305(16) 0.68057(5) 0.0518(4) Uani 1 1 d . . .
C14 C 0.14823(18) -0.07651(18) 0.70471(6) 0.0671(5) Uani 1 1 d . . .
H14 H 0.2265 -0.0967 0.7019 0.081 Uiso 1 1 calc R . .
C15 C 0.0808(2) -0.1562(2) 0.73292(7) 0.0821(6) Uani 1 1 d . . .
H15 H 0.1136 -0.2304 0.7487 0.099 Uiso 1 1 calc R . .
C16 C -0.0346(2) -0.1266(2) 0.73778(7) 0.0803(6) Uani 1 1 d . . .
H16 H -0.0795 -0.1800 0.7571 0.096 Uiso 1 1 calc R . .
C17 C -0.08327(19) -0.0187(2) 0.71419(6) 0.0752(6) Uani 1 1 d . . .
H17 H -0.1614 0.0012 0.7175 0.090 Uiso 1 1 calc R . .
C18 C -0.01677(16) 0.06112(18) 0.68533(6) 0.0630(5) Uani 1 1 d . . .
H18 H -0.0506 0.1337 0.6691 0.076 Uiso 1 1 calc R . .
C19 C 0.54908(16) 0.24867(19) 0.61104(6) 0.0635(5) Uani 1 1 d . . .
H19A H 0.5607 0.3055 0.6375 0.076 Uiso 1 1 calc R . .
H19B H 0.5182 0.3090 0.5878 0.076 Uiso 1 1 calc R . .
C20 C 0.66167(18) 0.1875(3) 0.59630(8) 0.0860(6) Uani 1 1 d . . .
H20A H 0.6505 0.1371 0.5685 0.103 Uiso 1 1 calc R . .
H20B H 0.7162 0.2634 0.5909 0.103 Uiso 1 1 calc R . .
C21 C 0.51437(16) 0.03477(18) 0.65319(7) 0.0679(5) Uani 1 1 d . . .
H21A H 0.4619 -0.0441 0.6569 0.081 Uiso 1 1 calc R . .
H21B H 0.5236 0.0809 0.6818 0.081 Uiso 1 1 calc R . .
C22 C 0.62889(19) -0.0169(2) 0.63685(8) 0.0837(6) Uani 1 1 d . . .
H22A H 0.6615 -0.0804 0.6588 0.100 Uiso 1 1 calc R . .
H22B H 0.6175 -0.0699 0.6096 0.100 Uiso 1 1 calc R . .


_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 C20 1.423(3) . ?
O1 C22 1.416(3) . ?
N1 N2 1.3521(19) . ?
N1 C6 1.323(2) . ?
N2 C3 1.330(2) . ?
N3 C5 1.360(2) . ?
N3 C19 1.466(2) . ?
N3 C21 1.467(2) . ?
N4 C3 1.340(2) . ?
N4 C5 1.3315(19) . ?
C3 C13 1.484(2) . ?
C5 C6 1.429(2) . ?
C6 C7 1.491(2) . ?
C7 C8 1.385(2) . ?
C7 C12 1.388(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(2) . ?
C13 C18 1.393(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.366(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.494(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.496(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 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
C22 O1 C20 109.61(16) . . ?
C6 N1 N2 120.95(14) . . ?
C3 N2 N1 116.52(14) . . ?
C5 N3 C19 122.18(14) . . ?
C5 N3 C21 119.06(14) . . ?
C19 N3 C21 111.45(14) . . ?
C5 N4 C3 117.30(13) . . ?
N2 C3 N4 125.49(15) . . ?
N2 C3 C13 117.16(14) . . ?
N4 C3 C13 117.34(14) . . ?
N3 C5 C6 124.53(14) . . ?
N4 C5 N3 117.33(14) . . ?
N4 C5 C6 118.11(14) . . ?
N1 C6 C5 119.38(14) . . ?
N1 C6 C7 114.32(14) . . ?
C5 C6 C7 126.12(15) . . ?
C8 C7 C6 119.94(15) . . ?
C8 C7 C12 118.67(15) . . ?
C12 C7 C6 121.25(15) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.59(19) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.96(18) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.55(18) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C3 119.99(16) . . ?
C14 C13 C18 118.65(16) . . ?
C18 C13 C3 121.34(15) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.59(19) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.96(19) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.17(18) . . ?
C17 C18 H18 119.9 . . ?
N3 C19 H19A 109.7 . . ?
N3 C19 H19B 109.7 . . ?
N3 C19 C20 109.70(15) . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
O1 C20 C19 111.77(17) . . ?
O1 C20 H20A 109.3 . . ?
O1 C20 H20B 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
N3 C21 H21A 109.9 . . ?
N3 C21 H21B 109.9 . . ?
N3 C21 C22 108.85(16) . . ?
H21A C21 H21B 108.3 . . ?
C22 C21 H21A 109.9 . . ?
C22 C21 H21B 109.9 . . ?
O1 C22 C21 112.93(17) . . ?
O1 C22 H22A 109.0 . . ?
O1 C22 H22B 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?

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
N1 N2 C3 N4 12.1(2) . . . . ?
N1 N2 C3 C13 -169.04(13) . . . . ?
N1 C6 C7 C8 37.5(2) . . . . ?
N1 C6 C7 C12 -138.17(16) . . . . ?
N2 N1 C6 C5 -7.7(2) . . . . ?
N2 N1 C6 C7 167.83(13) . . . . ?
N2 C3 C13 C14 178.03(14) . . . . ?
N2 C3 C13 C18 -0.5(2) . . . . ?
N3 C5 C6 N1 -166.16(15) . . . . ?
N3 C5 C6 C7 18.9(2) . . . . ?
N3 C19 C20 O1 -57.2(2) . . . . ?
N3 C21 C22 O1 56.7(2) . . . . ?
N4 C3 C13 C14 -3.0(2) . . . . ?
N4 C3 C13 C18 178.50(14) . . . . ?
N4 C5 C6 N1 15.7(2) . . . . ?
N4 C5 C6 C7 -159.18(14) . . . . ?
C3 N4 C5 N3 171.88(13) . . . . ?
C3 N4 C5 C6 -9.9(2) . . . . ?
C3 C13 C14 C15 -178.59(16) . . . . ?
C3 C13 C18 C17 179.33(15) . . . . ?
C5 N3 C19 C20 -155.15(16) . . . . ?
C5 N3 C21 C22 154.94(16) . . . . ?
C5 N4 C3 N2 -4.0(2) . . . . ?
C5 N4 C3 C13 177.17(13) . . . . ?
C5 C6 C7 C8 -147.37(16) . . . . ?
C5 C6 C7 C12 37.0(2) . . . . ?
C6 N1 N2 C3 -5.6(2) . . . . ?
C6 C7 C8 C9 -175.59(17) . . . . ?
C6 C7 C12 C11 175.63(16) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C13 C18 C17 0.8(2) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C13 -0.8(3) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
C19 N3 C5 N4 -145.07(15) . . . . ?
C19 N3 C5 C6 36.8(2) . . . . ?
C19 N3 C21 C22 -54.24(19) . . . . ?
C20 O1 C22 C21 -59.0(2) . . . . ?
C21 N3 C5 N4 2.5(2) . . . . ?
C21 N3 C5 C6 -175.61(14) . . . . ?
C21 N3 C19 C20 55.09(19) . . . . ?
C22 O1 C20 C19 58.7(2) . . . . ?
