# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ns1
_database_code_depnum_ccdc_archive 'CCDC 1419344'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-12-17 downloaded from the CCDC.
;

_audit_creation_method           'Masnual edit of SHELXL-97 Cif'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'pyrimidine derivative'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 N4 O4'
_chemical_formula_sum            'C20 H18 N4 O4'
_chemical_formula_weight         378.38

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
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   7.8274(3)
_cell_length_b                   11.2215(5)
_cell_length_c                   11.4253(5)
_cell_angle_alpha                71.279(2)
_cell_angle_beta                 72.2245(18)
_cell_angle_gamma                71.6451(19)
_cell_volume                     878.51(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    800
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   'SADABS; (sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18207
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3097
_reflns_number_gt                2422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Siemens)'
_computing_publication_material  SHELXL-97

_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)+(0.0965P)²+0.3679P] 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         3097
_refine_ls_number_parameters     254
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1590
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.054
_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
O1 O 0.2127(3) 0.2341(3) 0.50965(19) 0.0926(8) Uani 1 1 d . . .
O2 O -0.0733(3) 0.3002(2) 0.61791(18) 0.0700(6) Uani 1 1 d . . .
O3 O -0.5165(4) 0.4521(4) 0.7710(4) 0.1564(17) Uani 1 1 d . . .
O4 O -0.4136(3) 0.2751(3) 0.8892(3) 0.0881(7) Uani 1 1 d . . .
N1 N 0.2590(2) 0.04875(18) 1.09026(17) 0.0416(5) Uani 1 1 d . . .
N2 N 0.0543(2) 0.14823(16) 0.96551(16) 0.0361(4) Uani 1 1 d . . .
N3 N 0.3677(2) 0.09024(19) 0.86624(17) 0.0434(5) Uani 1 1 d . . .
H3A H 0.4809 0.0563 0.8715 0.052 Uiso 1 1 calc R . .
N4 N -0.4056(3) 0.3840(3) 0.8324(3) 0.0689(7) Uani 1 1 d . . .
C1 C 0.0805(3) 0.0766(2) 1.1659(2) 0.0393(5) Uani 1 1 d . . .
C2 C 0.0216(4) 0.0527(3) 1.2969(2) 0.0551(7) Uani 1 1 d . . .
H2A H 0.1049 0.0104 1.3490 0.066 Uiso 1 1 calc R . .
C3 C -0.1654(4) 0.0939(3) 1.3478(2) 0.0625(8) Uani 1 1 d . . .
H3B H -0.2071 0.0800 1.4353 0.075 Uiso 1 1 calc R . .
C4 C -0.2916(3) 0.1549(3) 1.2721(3) 0.0584(7) Uani 1 1 d . . .
H4A H -0.4161 0.1808 1.3097 0.070 Uiso 1 1 calc R . .
C5 C -0.2357(3) 0.1781(2) 1.1411(2) 0.0483(6) Uani 1 1 d . . .
H5A H -0.3200 0.2185 1.0896 0.058 Uiso 1 1 calc R . .
C6 C -0.0484(3) 0.13845(19) 1.0905(2) 0.0372(5) Uani 1 1 d . . .
C7 C 0.2329(3) 0.0945(2) 0.9743(2) 0.0362(5) Uani 1 1 d . . .
C8 C -0.0099(3) 0.2188(2) 0.8482(2) 0.0378(5) Uani 1 1 d . . .
H8A H -0.1098 0.1851 0.8457 0.045 Uiso 1 1 calc R . .
C9 C 0.1510(3) 0.1972(2) 0.7356(2) 0.0433(5) Uani 1 1 d . . .
C10 C 0.3262(3) 0.1392(2) 0.7489(2) 0.0452(6) Uani 1 1 d . . .
C11 C 0.4939(4) 0.1196(3) 0.6435(3) 0.0698(8) Uani 1 1 d . . .
H11A H 0.5348 0.0295 0.6431 0.105 Uiso 1 1 calc R . .
H11B H 0.5906 0.1464 0.6560 0.105 Uiso 1 1 calc R . .
H11C H 0.4638 0.1702 0.5638 0.105 Uiso 1 1 calc R . .
C12 C -0.0833(3) 0.3634(2) 0.84679(19) 0.0367(5) Uani 1 1 d . . .
C13 C -0.2607(3) 0.4381(2) 0.8382(2) 0.0493(6) Uani 1 1 d . . .
C14 C -0.3123(4) 0.5688(3) 0.8337(3) 0.0718(9) Uani 1 1 d . . .
H14A H -0.4320 0.6158 0.8278 0.086 Uiso 1 1 calc R . .
C15 C -0.1897(5) 0.6288(3) 0.8379(3) 0.0756(9) Uani 1 1 d . . .
H15A H -0.2250 0.7165 0.8363 0.091 Uiso 1 1 calc R . .
C16 C -0.0122(5) 0.5585(3) 0.8447(3) 0.0633(8) Uani 1 1 d . . .
H16A H 0.0735 0.5991 0.8464 0.076 Uiso 1 1 calc R . .
C17 C 0.0388(3) 0.4288(2) 0.8488(2) 0.0461(6) Uani 1 1 d . . .
H17A H 0.1595 0.3832 0.8531 0.055 Uiso 1 1 calc R . .
C18 C 0.1074(4) 0.2435(3) 0.6098(2) 0.0577(7) Uani 1 1 d . . .
C19 C -0.1260(6) 0.3548(5) 0.4972(4) 0.1033(14) Uani 1 1 d D . .
H19A H -0.0268 0.3886 0.4332 0.124 Uiso 1 1 calc R . .
H19B H -0.1479 0.2880 0.4708 0.124 Uiso 1 1 calc R . .
C20 C -0.2908(13) 0.4573(9) 0.5088(8) 0.280(6) Uani 1 1 d D . .
H20A H -0.3878 0.4239 0.5735 0.420 Uiso 1 1 calc R . .
H20B H -0.3277 0.4914 0.4294 0.420 Uiso 1 1 calc R . .
H20C H -0.2670 0.5250 0.5314 0.420 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 C18 1.203(3) . ?
O2 C18 1.343(3) . ?
O2 C19 1.447(4) . ?
O3 N4 1.200(3) . ?
O4 N4 1.197(3) . ?
N1 C7 1.313(3) . ?
N1 C1 1.399(3) . ?
N2 C7 1.358(3) . ?
N2 C6 1.397(3) . ?
N2 C8 1.468(3) . ?
N3 C7 1.360(3) . ?
N3 C10 1.373(3) . ?
N3 H3A 0.8600 . ?
N4 C13 1.471(4) . ?
C1 C2 1.387(3) . ?
C1 C6 1.395(3) . ?
C2 C3 1.386(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5A 0.9300 . ?
C8 C9 1.523(3) . ?
C8 C12 1.538(3) . ?
C8 H8A 0.9800 . ?
C9 C10 1.352(3) . ?
C9 C18 1.470(3) . ?
C10 C11 1.499(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.385(3) . ?
C12 C13 1.392(3) . ?
C13 C14 1.381(4) . ?
C14 C15 1.353(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.377(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C19 C20 1.436(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
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
C18 O2 C19 114.6(3) . . ?
C7 N1 C1 103.35(17) . . ?
C7 N2 C6 105.43(17) . . ?
C7 N2 C8 126.03(17) . . ?
C6 N2 C8 127.93(17) . . ?
C7 N3 C10 121.15(18) . . ?
C7 N3 H3A 119.4 . . ?
C10 N3 H3A 119.4 . . ?
O4 N4 O3 121.0(3) . . ?
O4 N4 C13 120.6(2) . . ?
O3 N4 C13 118.4(3) . . ?
C2 C1 C6 119.7(2) . . ?
C2 C1 N1 129.8(2) . . ?
C6 C1 N1 110.52(18) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3B 119.0 . . ?
C2 C3 H3B 119.0 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 116.9(2) . . ?
C6 C5 H5A 121.5 . . ?
C4 C5 H5A 121.5 . . ?
C5 C6 C1 122.6(2) . . ?
C5 C6 N2 132.0(2) . . ?
C1 C6 N2 105.38(17) . . ?
N1 C7 N2 115.30(18) . . ?
N1 C7 N3 125.45(19) . . ?
N2 C7 N3 119.24(19) . . ?
N2 C8 C9 108.53(17) . . ?
N2 C8 C12 108.84(16) . . ?
C9 C8 C12 111.47(18) . . ?
N2 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C12 C8 H8A 109.3 . . ?
C10 C9 C18 121.0(2) . . ?
C10 C9 C8 122.4(2) . . ?
C18 C9 C8 116.6(2) . . ?
C9 C10 N3 121.6(2) . . ?
C9 C10 C11 126.1(2) . . ?
N3 C10 C11 112.3(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 115.8(2) . . ?
C17 C12 C8 117.90(19) . . ?
C13 C12 C8 126.3(2) . . ?
C14 C13 C12 122.1(2) . . ?
C14 C13 N4 115.3(2) . . ?
C12 C13 N4 122.6(2) . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15A 120.4 . . ?
C16 C15 H15A 120.4 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C12 122.3(2) . . ?
C16 C17 H17A 118.9 . . ?
C12 C17 H17A 118.9 . . ?
O1 C18 O2 121.5(3) . . ?
O1 C18 C9 127.2(3) . . ?
O2 C18 C9 111.2(2) . . ?
C20 C19 O2 109.6(4) . . ?
C20 C19 H19A 109.7 . . ?
O2 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
O2 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C7 N1 C1 C2 -179.0(2) . . . . ?
C7 N1 C1 C6 0.5(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
N1 C1 C2 C3 178.4(2) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 N2 -178.7(2) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
N1 C1 C6 C5 -179.4(2) . . . . ?
C2 C1 C6 N2 179.7(2) . . . . ?
N1 C1 C6 N2 0.2(2) . . . . ?
C7 N2 C6 C5 178.7(2) . . . . ?
C8 N2 C6 C5 7.4(4) . . . . ?
C7 N2 C6 C1 -0.7(2) . . . . ?
C8 N2 C6 C1 -172.09(19) . . . . ?
C1 N1 C7 N2 -1.0(2) . . . . ?
C1 N1 C7 N3 180.0(2) . . . . ?
C6 N2 C7 N1 1.1(2) . . . . ?
C8 N2 C7 N1 172.73(19) . . . . ?
C6 N2 C7 N3 -179.78(18) . . . . ?
C8 N2 C7 N3 -8.2(3) . . . . ?
C10 N3 C7 N1 179.0(2) . . . . ?
C10 N3 C7 N2 0.0(3) . . . . ?
C7 N2 C8 C9 12.1(3) . . . . ?
C6 N2 C8 C9 -178.21(19) . . . . ?
C7 N2 C8 C12 -109.4(2) . . . . ?
C6 N2 C8 C12 60.3(3) . . . . ?
N2 C8 C9 C10 -9.4(3) . . . . ?
C12 C8 C9 C10 110.4(2) . . . . ?
N2 C8 C9 C18 170.9(2) . . . . ?
C12 C8 C9 C18 -69.2(3) . . . . ?
C18 C9 C10 N3 -177.0(2) . . . . ?
C8 C9 C10 N3 3.3(4) . . . . ?
C18 C9 C10 C11 2.7(4) . . . . ?
C8 C9 C10 C11 -176.9(2) . . . . ?
C7 N3 C10 C9 2.1(3) . . . . ?
C7 N3 C10 C11 -177.6(2) . . . . ?
N2 C8 C12 C17 61.2(2) . . . . ?
C9 C8 C12 C17 -58.5(3) . . . . ?
N2 C8 C12 C13 -121.8(2) . . . . ?
C9 C8 C12 C13 118.6(2) . . . . ?
C17 C12 C13 C14 -0.8(4) . . . . ?
C8 C12 C13 C14 -177.9(2) . . . . ?
C17 C12 C13 N4 178.7(2) . . . . ?
C8 C12 C13 N4 1.6(4) . . . . ?
O4 N4 C13 C14 -146.1(3) . . . . ?
O3 N4 C13 C14 33.0(4) . . . . ?
O4 N4 C13 C12 34.4(4) . . . . ?
O3 N4 C13 C12 -146.6(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
N4 C13 C14 C15 -179.8(3) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
C13 C12 C17 C16 1.0(3) . . . . ?
C8 C12 C17 C16 178.4(2) . . . . ?
C19 O2 C18 O1 -3.7(5) . . . . ?
C19 O2 C18 C9 176.8(3) . . . . ?
C10 C9 C18 O1 1.8(5) . . . . ?
C8 C9 C18 O1 -178.5(3) . . . . ?
C10 C9 C18 O2 -178.7(2) . . . . ?
C8 C9 C18 O2 1.0(3) . . . . ?
C18 O2 C19 C20 -154.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.055
