# 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_1
_database_code_depnum_ccdc_archive 'CCDC 968994'
_audit_update_record             
;
2013-10-28 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5,5'-(furan-2-ylmethylene)bis(6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione)
 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C17 H20 N6 O5'
_chemical_formula_sum            'C18 H24 N6 O4'
_chemical_formula_weight         388.43

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   P121/C1

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

_cell_length_a                   11.3123(8)
_cell_length_b                   14.8291(10)
_cell_length_c                   10.8777(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.943(7)
_cell_angle_gamma                90.00
_cell_volume                     1778.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1896
_cell_measurement_theta_min      3.9970
_cell_measurement_theta_max      28.1330

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6278
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3121
_reflns_number_gt                2109
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0606P)²+0.0054P] 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     SHELXL
_refine_ls_extinction_coef       0.0060(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3121
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.003
_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
O10 O 0.27080(16) 0.07505(11) 0.10753(17) 0.0422(5) Uani 1 1 d . . .
O24 O 0.06495(17) 0.36414(12) -0.00479(18) 0.0519(6) Uani 1 1 d . . .
O6 O 0.02863(16) 0.37694(12) 0.26519(18) 0.0456(5) Uani 1 1 d . . .
N1 N -0.13586(19) 0.28876(14) 0.2632(2) 0.0416(6) Uani 1 1 d . . .
O8 O 0.56153(17) 0.11302(14) 0.46852(19) 0.0595(6) Uani 1 1 d . . .
N9 N 0.41765(18) 0.09515(14) 0.2863(2) 0.0385(6) Uani 1 1 d . . .
N7 N 0.42466(19) 0.22600(15) 0.4080(2) 0.0422(6) Uani 1 1 d . . .
C19 C 0.1464(2) 0.23762(16) 0.1362(2) 0.0320(6) Uani 1 1 d . . .
H19 H 0.1367 0.1947 0.0661 0.038 Uiso 1 1 calc R . .
N3 N -0.14274(18) 0.13792(13) 0.1988(2) 0.0385(6) Uani 1 1 d . . .
O2 O -0.30081(17) 0.20132(13) 0.2655(2) 0.0593(6) Uani 1 1 d . . .
C4 C -0.0311(2) 0.14722(16) 0.1685(2) 0.0337(6) Uani 1 1 d . . .
C11 C 0.2609(2) 0.20673(16) 0.2272(2) 0.0328(6) Uani 1 1 d . . .
C10 C 0.3134(2) 0.12422(17) 0.2016(2) 0.0345(6) Uani 1 1 d . . .
C12 C 0.3164(2) 0.25529(17) 0.3342(2) 0.0351(6) Uani 1 1 d . . .
C5 C 0.0285(2) 0.22920(15) 0.1815(2) 0.0311(6) Uani 1 1 d . . .
C20 C 0.1620(2) 0.32737(16) 0.0767(2) 0.0344(6) Uani 1 1 d . . .
C8 C 0.4743(2) 0.14217(19) 0.3922(3) 0.0428(7) Uani 1 1 d . . .
N15 N 0.01342(19) 0.07200(13) 0.1253(2) 0.0427(6) Uani 1 1 d . . .
H15A H 0.0822 0.0736 0.1042 0.051 Uiso 1 1 calc R . .
H15B H -0.0271 0.0225 0.1189 0.051 Uiso 1 1 calc R . .
N18 N 0.27093(19) 0.33180(15) 0.3688(2) 0.0457(6) Uani 1 1 d . . .
H18A H 0.3091 0.3603 0.4346 0.055 Uiso 1 1 calc R . .
H18B H 0.2034 0.3526 0.3253 0.055 Uiso 1 1 calc R . .
C6 C -0.0215(2) 0.30184(17) 0.2365(2) 0.0361(6) Uani 1 1 d . . .
C2 C -0.1999(2) 0.20922(19) 0.2442(3) 0.0410(7) Uani 1 1 d . . .
C21 C 0.2599(2) 0.37706(16) 0.0803(2) 0.0360(6) Uani 1 1 d . . .
H21 H 0.3376 0.3648 0.1272 0.043 Uiso 1 1 calc R . .
C22 C 0.2254(3) 0.4519(2) 0.0003(3) 0.0528(8) Uani 1 1 d . . .
H22 H 0.2755 0.4984 -0.0147 0.063 Uiso 1 1 calc R . .
C14 C -0.2093(3) 0.05255(18) 0.1793(3) 0.0586(9) Uani 1 1 d . . .
H14A H -0.2840 0.0586 0.2066 0.088 Uiso 1 1 calc R . .
H14B H -0.1610 0.0058 0.2271 0.088 Uiso 1 1 calc R . .
H14C H -0.2267 0.0372 0.0913 0.088 Uiso 1 1 calc R . .
C16 C 0.4928(3) 0.2802(2) 0.5129(3) 0.0618(9) Uani 1 1 d . . .
H16A H 0.4915 0.3424 0.4878 0.093 Uiso 1 1 calc R . .
H16B H 0.5752 0.2594 0.5353 0.093 Uiso 1 1 calc R . .
H16C H 0.4565 0.2744 0.5842 0.093 Uiso 1 1 calc R . .
C17 C 0.4721(3) 0.00857(18) 0.2659(3) 0.0549(8) Uani 1 1 d . . .
H17A H 0.5585 0.0154 0.2796 0.082 Uiso 1 1 calc R . .
H17B H 0.4401 -0.0112 0.1809 0.082 Uiso 1 1 calc R . .
H17C H 0.4536 -0.0353 0.3238 0.082 Uiso 1 1 calc R . .
C13 C -0.1927(3) 0.3648(2) 0.3138(3) 0.0656(10) Uani 1 1 d . . .
H13A H -0.2731 0.3482 0.3202 0.098 Uiso 1 1 calc R . .
H13B H -0.1969 0.4157 0.2584 0.098 Uiso 1 1 calc R . .
H13C H -0.1454 0.3803 0.3958 0.098 Uiso 1 1 calc R . .
C23 C 0.1077(3) 0.44310(18) -0.0493(3) 0.0516(8) Uani 1 1 d . . .
H23 H 0.0608 0.4834 -0.1053 0.062 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
O10 C10 1.261(3) . ?
O24 C20 1.361(3) . ?
O24 C23 1.394(3) . ?
O6 C6 1.257(3) . ?
N1 C2 1.376(3) . ?
N1 C6 1.401(3) . ?
N1 C13 1.465(3) . ?
O8 C8 1.218(3) . ?
N9 C8 1.376(3) . ?
N9 C10 1.392(3) . ?
N9 C17 1.463(3) . ?
N7 C12 1.376(3) . ?
N7 C8 1.390(3) . ?
N7 C16 1.466(3) . ?
C19 C20 1.507(3) . ?
C19 C11 1.514(3) . ?
C19 C5 1.527(3) . ?
C19 H19 0.9800 . ?
N3 C4 1.382(3) . ?
N3 C2 1.387(3) . ?
N3 C14 1.464(3) . ?
O2 C2 1.220(3) . ?
C4 N15 1.351(3) . ?
C4 C5 1.382(3) . ?
C11 C12 1.393(3) . ?
C11 C10 1.415(3) . ?
C12 N18 1.334(3) . ?
C5 C6 1.411(3) . ?
C20 C21 1.324(3) . ?
N15 H15A 0.8600 . ?
N15 H15B 0.8600 . ?
N18 H18A 0.8600 . ?
N18 H18B 0.8600 . ?
C21 C22 1.410(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.326(4) . ?
C22 H22 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C23 H23 0.9300 . ?

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
C20 O24 C23 105.7(2) . . ?
C2 N1 C6 124.6(2) . . ?
C2 N1 C13 117.1(2) . . ?
C6 N1 C13 118.3(2) . . ?
C8 N9 C10 124.3(2) . . ?
C8 N9 C17 116.0(2) . . ?
C10 N9 C17 119.6(2) . . ?
C12 N7 C8 122.8(2) . . ?
C12 N7 C16 121.7(2) . . ?
C8 N7 C16 115.5(2) . . ?
C20 C19 C11 112.5(2) . . ?
C20 C19 C5 113.9(2) . . ?
C11 C19 C5 116.5(2) . . ?
C20 C19 H19 104.1 . . ?
C11 C19 H19 104.1 . . ?
C5 C19 H19 104.1 . . ?
C4 N3 C2 122.2(2) . . ?
C4 N3 C14 121.3(2) . . ?
C2 N3 C14 116.4(2) . . ?
N15 C4 C5 123.4(2) . . ?
N15 C4 N3 115.6(2) . . ?
C5 C4 N3 120.9(2) . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 C19 123.3(2) . . ?
C10 C11 C19 117.9(2) . . ?
O10 C10 N9 118.1(2) . . ?
O10 C10 C11 124.0(2) . . ?
N9 C10 C11 117.9(2) . . ?
N18 C12 N7 116.9(2) . . ?
N18 C12 C11 123.1(2) . . ?
N7 C12 C11 120.0(2) . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 C19 118.7(2) . . ?
C6 C5 C19 122.5(2) . . ?
C21 C20 O24 110.1(2) . . ?
C21 C20 C19 131.0(2) . . ?
O24 C20 C19 118.6(2) . . ?
O8 C8 N9 123.0(3) . . ?
O8 C8 N7 121.4(3) . . ?
N9 C8 N7 115.6(2) . . ?
C4 N15 H15A 120.0 . . ?
C4 N15 H15B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
C12 N18 H18A 120.0 . . ?
C12 N18 H18B 120.0 . . ?
H18A N18 H18B 120.0 . . ?
O6 C6 N1 117.2(2) . . ?
O6 C6 C5 125.4(2) . . ?
N1 C6 C5 117.3(2) . . ?
O2 C2 N1 122.5(3) . . ?
O2 C2 N3 121.7(3) . . ?
N1 C2 N3 115.8(2) . . ?
C20 C21 C22 107.8(2) . . ?
C20 C21 H21 126.1 . . ?
C22 C21 H21 126.1 . . ?
C23 C22 C21 106.8(2) . . ?
C23 C22 H22 126.6 . . ?
C21 C22 H22 126.6 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N7 C16 H16A 109.5 . . ?
N7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N9 C17 H17A 109.5 . . ?
N9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C22 C23 O24 109.6(2) . . ?
C22 C23 H23 125.2 . . ?
O24 C23 H23 125.2 . . ?

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
C2 N3 C4 N15 -179.9(2) . . . . ?
C14 N3 C4 N15 -2.6(4) . . . . ?
C2 N3 C4 C5 -0.5(4) . . . . ?
C14 N3 C4 C5 176.8(2) . . . . ?
C20 C19 C11 C12 60.3(3) . . . . ?
C5 C19 C11 C12 -73.8(3) . . . . ?
C20 C19 C11 C10 -119.8(2) . . . . ?
C5 C19 C11 C10 106.1(3) . . . . ?
C8 N9 C10 O10 179.5(2) . . . . ?
C17 N9 C10 O10 -1.6(3) . . . . ?
C8 N9 C10 C11 -1.2(4) . . . . ?
C17 N9 C10 C11 177.7(2) . . . . ?
C12 C11 C10 O10 -179.9(2) . . . . ?
C19 C11 C10 O10 0.2(4) . . . . ?
C12 C11 C10 N9 0.8(3) . . . . ?
C19 C11 C10 N9 -179.1(2) . . . . ?
C8 N7 C12 N18 171.7(2) . . . . ?
C16 N7 C12 N18 -5.5(4) . . . . ?
C8 N7 C12 C11 -9.8(4) . . . . ?
C16 N7 C12 C11 173.0(2) . . . . ?
C10 C11 C12 N18 -177.2(2) . . . . ?
C19 C11 C12 N18 2.7(4) . . . . ?
C10 C11 C12 N7 4.4(4) . . . . ?
C19 C11 C12 N7 -175.7(2) . . . . ?
N15 C4 C5 C6 -175.2(2) . . . . ?
N3 C4 C5 C6 5.4(4) . . . . ?
N15 C4 C5 C19 4.5(4) . . . . ?
N3 C4 C5 C19 -174.9(2) . . . . ?
C20 C19 C5 C4 142.9(2) . . . . ?
C11 C19 C5 C4 -83.6(3) . . . . ?
C20 C19 C5 C6 -37.4(3) . . . . ?
C11 C19 C5 C6 96.1(3) . . . . ?
C23 O24 C20 C21 -2.2(3) . . . . ?
C23 O24 C20 C19 -176.8(2) . . . . ?
C11 C19 C20 C21 8.4(4) . . . . ?
C5 C19 C20 C21 143.7(3) . . . . ?
C11 C19 C20 O24 -178.4(2) . . . . ?
C5 C19 C20 O24 -43.1(3) . . . . ?
C10 N9 C8 O8 175.9(2) . . . . ?
C17 N9 C8 O8 -3.0(4) . . . . ?
C10 N9 C8 N7 -3.6(4) . . . . ?
C17 N9 C8 N7 177.5(2) . . . . ?
C12 N7 C8 O8 -170.3(2) . . . . ?
C16 N7 C8 O8 7.1(4) . . . . ?
C12 N7 C8 N9 9.1(4) . . . . ?
C16 N7 C8 N9 -173.5(2) . . . . ?
C2 N1 C6 O6 -176.3(2) . . . . ?
C13 N1 C6 O6 4.3(4) . . . . ?
C2 N1 C6 C5 2.8(4) . . . . ?
C13 N1 C6 C5 -176.6(2) . . . . ?
C4 C5 C6 O6 172.7(2) . . . . ?
C19 C5 C6 O6 -7.0(4) . . . . ?
C4 C5 C6 N1 -6.4(4) . . . . ?
C19 C5 C6 N1 174.0(2) . . . . ?
C6 N1 C2 O2 -178.0(2) . . . . ?
C13 N1 C2 O2 1.4(4) . . . . ?
C6 N1 C2 N3 1.9(4) . . . . ?
C13 N1 C2 N3 -178.7(2) . . . . ?
C4 N3 C2 O2 176.8(2) . . . . ?
C14 N3 C2 O2 -0.7(4) . . . . ?
C4 N3 C2 N1 -3.2(4) . . . . ?
C14 N3 C2 N1 179.4(2) . . . . ?
O24 C20 C21 C22 1.9(3) . . . . ?
C19 C20 C21 C22 175.6(3) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C21 C22 C23 O24 -0.6(3) . . . . ?
C20 O24 C23 C22 1.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.046








