#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:20:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180501 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/70/7217014.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7217014
loop_
_publ_author_name
'Roviello, Giovanni N.'
'Roviello, Giuseppina'
'Musumeci, Domenica'
'Capasso, Domenica'
'Di Gaetano, Sonia'
'Costanzo, Michele'
'Pedone, Carlo'
_publ_section_title
;
 Synthesis and supramolecular assembly of
 1,3-bis(1′-uracilyl)-2-propanone
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              28691
_journal_paper_doi               10.1039/c4ra03713h
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C11 H10 N4 O5'
_chemical_formula_sum            'C11 H10 N4 O5'
_chemical_formula_weight         278.23
_chemical_name_systematic        1,3-bis(1-uracilyl)-propan-2-one
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 130.93(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.061(5)
_cell_length_b                   4.938(2)
_cell_length_c                   20.805(3)
_cell_measurement_reflns_used    160
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      19.210
_cell_measurement_theta_min      3.025
_cell_volume                     1169.0(7)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11761
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.58
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker, 2000)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0710
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2209
_refine_ls_wR_factor_ref         0.2947
_reflns_number_gt                1733
_reflns_number_total             2645
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra03713h2.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1168.9(1)
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               7217014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
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
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_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'
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_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_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_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
