# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1504789'
_audit_update_record             
;
2016-09-18 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N4 O2'
_chemical_formula_weight         348.40

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.3993(3)
_cell_length_b                   11.0228(5)
_cell_length_c                   13.8844(9)
_cell_angle_alpha                106.376(5)
_cell_angle_beta                 98.689(5)
_cell_angle_gamma                106.505(3)
_cell_volume                     872.02(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1873
_cell_measurement_theta_min      2.9879
_cell_measurement_theta_max      24.0651

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7525
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3928
_reflns_number_gt                2693
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0772P)²+0.0309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3928
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.3286(2) 0.15731(13) 0.76507(10) 0.0433(3) Uani 1 1 d . . .
N2 N 0.9803(3) 0.23817(17) 1.05869(14) 0.0613(4) Uani 1 1 d . . .
N3 N 0.7143(2) 0.48428(13) 1.06167(11) 0.0518(4) Uani 1 1 d . . .
N4 N 0.5516(2) 0.36537(13) 0.99874(11) 0.0487(4) Uani 1 1 d . . .
H4 H 0.4198 0.3602 0.9690 0.058 Uiso 1 1 calc R . .
C1 C 0.4048(3) 0.20193(15) 0.68577(12) 0.0418(4) Uani 1 1 d . . .
C2 C 0.5346(3) 0.14731(16) 0.62704(13) 0.0481(4) Uani 1 1 d . . .
H2 H 0.5668 0.0732 0.6353 0.058 Uiso 1 1 calc R . .
C3 C 0.6165(3) 0.2023(2) 0.55637(14) 0.0623(5) Uani 1 1 d . . .
H3 H 0.7058 0.1658 0.5186 0.075 Uiso 1 1 calc R . .
C4 C 0.5674(4) 0.3104(2) 0.54125(15) 0.0709(6) Uani 1 1 d . . .
H4A H 0.6226 0.3470 0.4936 0.085 Uiso 1 1 calc R . .
C5 C 0.4355(4) 0.3634(2) 0.59764(16) 0.0699(6) Uani 1 1 d . . .
H5 H 0.4007 0.4360 0.5876 0.084 Uiso 1 1 calc R . .
C6 C 0.3543(3) 0.31061(18) 0.66872(14) 0.0560(5) Uani 1 1 d . . .
H6 H 0.2648 0.3477 0.7059 0.067 Uiso 1 1 calc R . .
C7 C 0.0821(3) 0.09689(18) 0.74421(15) 0.0560(5) Uani 1 1 d . . .
H7A H 0.0119 0.1537 0.7199 0.067 Uiso 1 1 calc R . .
H7B H 0.0420 0.0923 0.8081 0.067 Uiso 1 1 calc R . .
C8 C -0.0067(3) -0.04329(19) 0.66366(17) 0.0619(5) Uani 1 1 d . . .
H8A H -0.1647 -0.0850 0.6595 0.074 Uiso 1 1 calc R . .
H8B H 0.0057 -0.0369 0.5964 0.074 Uiso 1 1 calc R . .
C9 C 0.1217(3) -0.13065(17) 0.68969(14) 0.0505(4) Uani 1 1 d . . .
C10 C 0.0285(3) -0.27099(18) 0.64872(15) 0.0634(5) Uani 1 1 d . . .
H10 H -0.1162 -0.3113 0.6053 0.076 Uiso 1 1 calc R . .
C11 C 0.1444(4) -0.35078(19) 0.67077(16) 0.0650(5) Uani 1 1 d . . .
H11 H 0.0784 -0.4440 0.6424 0.078 Uiso 1 1 calc R . .
C12 C 0.3587(3) -0.29315(17) 0.73494(14) 0.0580(5) Uani 1 1 d . . .
H12 H 0.4386 -0.3471 0.7495 0.070 Uiso 1 1 calc R . .
C13 C 0.4542(3) -0.15466(16) 0.77755(13) 0.0498(4) Uani 1 1 d . . .
H13 H 0.5984 -0.1157 0.8214 0.060 Uiso 1 1 calc R . .
C14 C 0.3370(3) -0.07208(15) 0.75570(12) 0.0425(4) Uani 1 1 d . . .
C15 C 0.4445(3) 0.07977(15) 0.80780(12) 0.0410(4) Uani 1 1 d . . .
H15 H 0.5981 0.1060 0.7989 0.049 Uiso 1 1 calc R . .
C16 C 0.4613(3) 0.11879(15) 0.92537(12) 0.0473(4) Uani 1 1 d . . .
H16A H 0.3121 0.1091 0.9362 0.057 Uiso 1 1 calc R . .
H16B H 0.5133 0.0563 0.9507 0.057 Uiso 1 1 calc R . .
C17 C 0.6152(3) 0.25853(15) 0.98757(12) 0.0413(4) Uani 1 1 d . . .
C18 C 0.8353(3) 0.31165(15) 1.04752(12) 0.0421(4) Uani 1 1 d . . .
C19 C 0.8898(3) 0.45202(17) 1.09318(12) 0.0450(4) Uani 1 1 d . . .
C20 C 1.0983(3) 0.5577(2) 1.16546(14) 0.0612(5) Uani 1 1 d . . .
H20A H 1.0900 0.6449 1.1710 0.092 Uiso 1 1 calc R . .
H20B H 1.2260 0.5484 1.1396 0.092 Uiso 1 1 calc R . .
H20C H 1.1141 0.5483 1.2326 0.092 Uiso 1 1 calc R . .
O1 O 1.1615(3) 0.29569(18) 1.12247(14) 0.0985(6) Uani 1 1 d . . .
O2 O 0.9220(3) 0.12050(17) 1.00114(16) 0.1033(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 1.4224(19) . ?
N1 C15 1.4645(19) . ?
N1 C7 1.474(2) . ?
N2 O1 1.219(2) . ?
N2 O2 1.229(2) . ?
N2 C18 1.413(2) . ?
N3 C19 1.321(2) . ?
N3 N4 1.3673(19) . ?
N4 C17 1.3285(19) . ?
C1 C2 1.389(2) . ?
C1 C6 1.397(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.378(3) . ?
C4 C5 1.374(3) . ?
C5 C6 1.374(3) . ?
C7 C8 1.515(3) . ?
C8 C9 1.513(2) . ?
C9 C14 1.391(2) . ?
C9 C10 1.396(2) . ?
C10 C11 1.368(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.380(2) . ?
C13 C14 1.399(2) . ?
C14 C15 1.520(2) . ?
C15 C16 1.545(2) . ?
C16 C17 1.490(2) . ?
C17 C18 1.386(2) . ?
C18 C19 1.411(2) . ?
C19 C20 1.483(2) . ?

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 C15 117.61(12) . . ?
C1 N1 C7 114.60(13) . . ?
C15 N1 C7 111.73(12) . . ?
O1 N2 O2 122.82(16) . . ?
O1 N2 C18 118.53(17) . . ?
O2 N2 C18 118.59(17) . . ?
C19 N3 N4 105.45(13) . . ?
C17 N4 N3 114.06(14) . . ?
C2 C1 C6 117.95(15) . . ?
C2 C1 N1 123.77(14) . . ?
C6 C1 N1 118.22(14) . . ?
C3 C2 C1 120.57(16) . . ?
C4 C3 C2 120.78(18) . . ?
C5 C4 C3 118.95(18) . . ?
C4 C5 C6 120.98(18) . . ?
C5 C6 C1 120.73(17) . . ?
N1 C7 C8 111.59(13) . . ?
C9 C8 C7 111.65(15) . . ?
C14 C9 C10 118.37(16) . . ?
C14 C9 C8 120.30(15) . . ?
C10 C9 C8 121.33(16) . . ?
C11 C10 C9 121.74(18) . . ?
C10 C11 C12 120.05(17) . . ?
C11 C12 C13 119.49(17) . . ?
C12 C13 C14 120.94(17) . . ?
C9 C14 C13 119.39(15) . . ?
C9 C14 C15 121.35(14) . . ?
C13 C14 C15 119.22(14) . . ?
N1 C15 C14 114.57(13) . . ?
N1 C15 C16 109.25(12) . . ?
C14 C15 C16 109.92(13) . . ?
C17 C16 C15 114.12(13) . . ?
N4 C17 C18 103.88(14) . . ?
N4 C17 C16 122.79(15) . . ?
C18 C17 C16 133.27(14) . . ?
C17 C18 C19 107.89(13) . . ?
C17 C18 N2 125.83(15) . . ?
C19 C18 N2 126.26(16) . . ?
N3 C19 C18 108.70(14) . . ?
N3 C19 C20 120.19(16) . . ?
C18 C19 C20 131.11(16) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.046
