# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl
#TrackingRef 'giovaOK.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'1,3-bis(1-uracilyl)-propan-2-one'

;
_chemical_formula_moiety         'C11 H10 N4 O5'
_chemical_formula_sum            'C11 H10 N4 O5'
_chemical_formula_weight         278.23

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   15.061(5)
_cell_length_b                   4.938(2)
_cell_length_c                   20.805(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.93(2)
_cell_angle_gamma                90.00
_cell_volume                     1168.9(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    160
_cell_measurement_theta_min      3.025
_cell_measurement_theta_max      19.210

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   
;
SADABS (Bruker, 2000)
;

_diffrn_ambient_temperature      173(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       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            11761
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2645
_reflns_number_gt                1733
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'

_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)+(0.2000P)²+0.0000P] 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_number_reflns         2645
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.2947
_refine_ls_wR_factor_gt          0.2209
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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 1.1518(2) 0.5607(5) 0.55318(14) 0.0347(6) Uani 1 1 d . . .
O2 O 0.9009(2) -0.0629(5) 0.35170(16) 0.0403(7) Uani 1 1 d . . .
O3 O 1.0000 0.1773(7) 0.2500 0.0558(12) Uani 1 2 d S . .
O4 O 0.6849(2) 0.6108(5) 0.08409(16) 0.0412(7) Uani 1 1 d . . .
O5 O 0.4848(2) -0.0919(5) 0.07673(13) 0.0338(6) Uani 1 1 d . . .
O6 O 0.5000 0.3898(8) 0.2500 0.0616(13) Uani 1 2 d S . .
N1 N 1.0300(2) 0.2407(5) 0.45449(16) 0.0300(7) Uani 1 1 d . . .
H1N H 0.9702 0.3169 0.4542 0.045(11) Uiso 1 1 d R . .
N2 N 1.0869(2) -0.0490(5) 0.39866(15) 0.0284(7) Uani 1 1 d . . .
N3 N 0.5914(2) 0.2538(5) 0.08454(15) 0.0293(7) Uani 1 1 d . . .
H3N H 0.5642 0.2025 0.0311 0.049(11) Uiso 1 1 d R . .
N4 N 0.6116(2) 0.1390(5) 0.20164(15) 0.0310(7) Uani 1 1 d . . .
C1 C 0.9993(3) 0.0357(6) 0.39854(19) 0.0295(7) Uani 1 1 d . . .
C2 C 1.1383(3) 0.3681(7) 0.50910(17) 0.0289(7) Uani 1 1 d . . .
C3 C 1.2252(3) 0.2622(7) 0.5079(2) 0.0336(8) Uani 1 1 d . . .
H3 H 1.3031 0.3316 0.5458 0.034 Uiso 1 1 calc R . .
C4 C 1.1969(3) 0.0641(7) 0.4530(2) 0.0325(8) Uani 1 1 d . . .
H4 H 1.2553 0.0001 0.4517 0.032 Uiso 1 1 calc R . .
C5 C 1.0533(3) -0.2274(6) 0.33010(17) 0.0290(7) Uani 1 1 d . . .
H5A H 0.9954 -0.3619 0.3182 0.029 Uiso 1 1 calc R . .
H5B H 1.1233 -0.3265 0.3476 0.029 Uiso 1 1 calc R . .
C6 C 1.0000 -0.0646(9) 0.2500 0.0301(10) Uani 1 2 d S . .
C7 C 0.5573(3) 0.0898(6) 0.11777(18) 0.0273(7) Uani 1 1 d . . .
C8 C 0.6684(3) 0.4706(7) 0.1244(2) 0.0308(7) Uani 1 1 d . . .
C9 C 0.7229(3) 0.5062(7) 0.2121(2) 0.0355(8) Uani 1 1 d . . .
H9 H 0.7796 0.6448 0.2452 0.036 Uiso 1 1 calc R . .
C10 C 0.6934(3) 0.3438(7) 0.24630(19) 0.0324(8) Uani 1 1 d . . .
H10 H 0.7303 0.3700 0.3043 0.032 Uiso 1 1 calc R . .
C11 C 0.5756(4) -0.0169(7) 0.2403(2) 0.0370(9) Uani 1 1 d . . .
H11A H 0.6465 -0.0806 0.2970 0.037 Uiso 1 1 calc R . .
H11B H 0.5314 -0.1783 0.2048 0.037 Uiso 1 1 calc R . .
C12 C 0.5000 0.1446(10) 0.2500 0.0366(11) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0324(13) 0.0409(13) 0.0259(11) -0.0099(9) 0.0170(10) -0.0046(10)
O2 0.0319(13) 0.0435(14) 0.0390(13) -0.0179(10) 0.0203(11) -0.0074(10)
O3 0.096(3) 0.0272(18) 0.0347(19) 0.000 0.039(2) 0.000
O4 0.0410(14) 0.0429(14) 0.0440(14) -0.0015(11) 0.0297(12) -0.0097(11)
O5 0.0354(13) 0.0388(13) 0.0256(11) -0.0063(9) 0.0192(10) -0.0114(10)
O6 0.092(3) 0.036(2) 0.103(4) 0.000 0.085(3) 0.000
N1 0.0260(13) 0.0368(16) 0.0238(12) -0.0055(10) 0.0147(11) -0.0005(11)
N2 0.0331(15) 0.0292(13) 0.0190(12) 0.0000(9) 0.0154(11) 0.0041(11)
N3 0.0306(14) 0.0359(15) 0.0211(12) -0.0067(10) 0.0168(11) -0.0081(11)
N4 0.0375(15) 0.0328(14) 0.0220(13) -0.0027(10) 0.0192(12) -0.0009(12)
C1 0.0284(16) 0.0347(16) 0.0230(14) 0.0001(12) 0.0158(13) 0.0020(13)
C2 0.0283(15) 0.0351(16) 0.0170(13) -0.0031(12) 0.0121(12) -0.0033(13)
C3 0.0273(15) 0.0420(18) 0.0279(15) -0.0061(13) 0.0165(13) -0.0013(13)
C4 0.0274(16) 0.0409(18) 0.0272(16) 0.0005(13) 0.0171(14) 0.0043(13)
C5 0.0319(16) 0.0309(16) 0.0217(14) 0.0004(11) 0.0165(13) 0.0051(12)
C6 0.034(2) 0.033(2) 0.021(2) 0.000 0.0170(19) 0.000
C7 0.0286(15) 0.0305(15) 0.0224(14) -0.0042(11) 0.0166(13) -0.0008(13)
C8 0.0262(16) 0.0335(16) 0.0332(16) -0.0021(13) 0.0197(14) -0.0012(12)
C9 0.0282(17) 0.0390(18) 0.0290(16) -0.0123(13) 0.0142(14) -0.0061(14)
C10 0.0293(16) 0.0367(17) 0.0215(14) -0.0096(12) 0.0125(13) -0.0017(14)
C11 0.056(2) 0.0330(17) 0.0295(16) 0.0013(13) 0.0312(17) 0.0023(16)
C12 0.053(3) 0.031(2) 0.034(2) 0.000 0.032(2) 0.000

_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 C2 1.242(4) . no
O2 C1 1.221(4) . no
O3 C6 1.194(6) . no
O4 C8 1.231(4) . no
O5 C7 1.227(4) . no
O6 C12 1.211(6) . no
N1 C1 1.374(4) . no
N1 C2 1.385(4) . no
N1 H1N 0.9727 . no
N2 C4 1.372(4) . no
N2 C1 1.382(4) . no
N2 C5 1.456(4) . no
N3 C7 1.364(4) . no
N3 C8 1.384(4) . no
N3 H3N 0.9334 . no
N4 C10 1.379(4) . no
N4 C7 1.380(4) . no
N4 C11 1.451(4) . no
C2 C3 1.425(5) . no
C3 C4 1.344(4) . no
C3 H3 0.9500 . no
C4 H4 0.9500 . no
C5 C6 1.522(4) . no
C5 H5A 0.9900 . no
C5 H5B 0.9900 . no
C6 C5 1.522(4) 2_755 no
C8 C9 1.439(4) . no
C9 C10 1.328(5) . no
C9 H9 0.9500 . no
C10 H10 0.9500 . no
C11 C12 1.508(5) . no
C11 H11A 0.9900 . no
C11 H11B 0.9900 . no
C12 C11 1.508(5) 2_655 no

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 C2 126.3(3) . . no
C1 N1 H1N 118.9 . . no
C2 N1 H1N 114.7 . . no
C4 N2 C1 121.0(3) . . no
C4 N2 C5 120.7(3) . . no
C1 N2 C5 117.5(3) . . no
C7 N3 C8 126.9(2) . . no
C7 N3 H3N 115.1 . . no
C8 N3 H3N 117.7 . . no
C10 N4 C7 120.6(3) . . no
C10 N4 C11 120.6(2) . . no
C7 N4 C11 118.8(3) . . no
O2 C1 N1 121.9(3) . . no
O2 C1 N2 122.6(3) . . no
N1 C1 N2 115.5(3) . . no
O1 C2 N1 119.2(3) . . no
O1 C2 C3 126.0(3) . . no
N1 C2 C3 114.9(3) . . no
C4 C3 C2 119.9(3) . . no
C4 C3 H3 120.0 . . no
C2 C3 H3 120.0 . . no
C3 C4 N2 122.4(3) . . no
C3 C4 H4 118.8 . . no
N2 C4 H4 118.8 . . no
N2 C5 C6 110.4(3) . . no
N2 C5 H5A 109.6 . . no
C6 C5 H5A 109.6 . . no
N2 C5 H5B 109.6 . . no
C6 C5 H5B 109.6 . . no
H5A C5 H5B 108.1 . . no
O3 C6 C5 121.89(18) . . no
O3 C6 C5 121.89(18) . 2_755 no
C5 C6 C5 116.2(4) . 2_755 no
O5 C7 N3 122.7(3) . . no
O5 C7 N4 121.9(3) . . no
N3 C7 N4 115.4(3) . . no
O4 C8 N3 119.4(3) . . no
O4 C8 C9 126.3(3) . . no
N3 C8 C9 114.3(3) . . no
C10 C9 C8 119.5(3) . . no
C10 C9 H9 120.2 . . no
C8 C9 H9 120.2 . . no
C9 C10 N4 123.1(3) . . no
C9 C10 H10 118.4 . . no
N4 C10 H10 118.4 . . no
N4 C11 C12 112.5(3) . . no
N4 C11 H11A 109.1 . . no
C12 C11 H11A 109.1 . . no
N4 C11 H11B 109.1 . . no
C12 C11 H11B 109.1 . . no
H11A C11 H11B 107.8 . . no
O6 C12 C11 121.9(2) . 2_655 no
O6 C12 C11 121.9(2) . . no
C11 C12 C11 116.2(4) 2_655 . no

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 N1 C1 O2 -179.0(3) . . . . no
C2 N1 C1 N2 0.6(5) . . . . no
C4 N2 C1 O2 -179.2(3) . . . . no
C5 N2 C1 O2 11.0(4) . . . . no
C4 N2 C1 N1 1.3(4) . . . . no
C5 N2 C1 N1 -168.5(3) . . . . no
C1 N1 C2 O1 176.3(3) . . . . no
C1 N1 C2 C3 -3.0(5) . . . . no
O1 C2 C3 C4 -175.6(3) . . . . no
N1 C2 C3 C4 3.6(4) . . . . no
C2 C3 C4 N2 -2.1(5) . . . . no
C1 N2 C4 C3 -0.5(5) . . . . no
C5 N2 C4 C3 169.0(3) . . . . no
C4 N2 C5 C6 -89.6(3) . . . . no
C1 N2 C5 C6 80.3(3) . . . . no
N2 C5 C6 O3 7.4(3) . . . . no
N2 C5 C6 C5 -172.6(3) . . . 2_755 no
C8 N3 C7 O5 177.0(3) . . . . no
C8 N3 C7 N4 -4.1(5) . . . . no
C10 N4 C7 O5 179.6(3) . . . . no
C11 N4 C7 O5 -4.3(5) . . . . no
C10 N4 C7 N3 0.7(4) . . . . no
C11 N4 C7 N3 176.7(3) . . . . no
C7 N3 C8 O4 -175.4(3) . . . . no
C7 N3 C8 C9 5.1(5) . . . . no
O4 C8 C9 C10 177.8(3) . . . . no
N3 C8 C9 C10 -2.8(5) . . . . no
C8 C9 C10 N4 -0.1(5) . . . . no
C7 N4 C10 C9 1.2(5) . . . . no
C11 N4 C10 C9 -174.7(3) . . . . no
C10 N4 C11 C12 71.4(4) . . . . no
C7 N4 C11 C12 -104.6(3) . . . . no
N4 C11 C12 O6 -20.8(3) . . . . no
N4 C11 C12 C11 159.2(3) . . . 2_655 no

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.110


_database_code_depnum_ccdc_archive 'CCDC 932679'
