#------------------------------------------------------------------------------ #$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2015358.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2015358 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Borowiak, Teresa' 'Dutkiewicz, Grzegorz' 'Spycha\/la, Jaros\/law' _publ_section_title ; Molecular packing in (5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetamide ; _journal_coeditor_code GD3012 _journal_issue 6 _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o344 _journal_page_last o345 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C7 H9 N3 O3' _chemical_formula_moiety 'C7 H9 N3 O3' _chemical_formula_sum 'C7 H9 N3 O3' _chemical_formula_weight 183.17 _chemical_name_common (1-thyminyl)acetamide _chemical_name_systematic ; (1-thyminyl)acetamide(5-methyl-2,4-dioxo-1,2,3,4- tetrahydropyrimidin-1-yl)acetamide ; _symmetry_cell_setting monoclinic _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 92.9230(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.03880(10) _cell_length_b 6.14760(10) _cell_length_c 15.83900(10) _cell_measurement_reflns_used 35533 _cell_measurement_temperature 100.0(10) _cell_measurement_theta_max 30 _cell_measurement_theta_min 3.52 _cell_volume 781.74(2) _computing_cell_refinement 'CrysAlis CCD' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2004)' _computing_molecular_graphics 'Stereochemical Workstation Operation Manual (Siemens, 1989)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100.0(10) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Kuma KM-4 CCD four-circle' _diffrn_measurement_method \w _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 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 30900 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 3.52 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.416 _refine_diff_density_min -0.265 _refine_ls_extinction_coef 0.021(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2287 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0363 _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/[\s^2^(Fo^2^)+(0.0479P)^2^+0.3534P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0939 _refine_ls_wR_factor_ref 0.0942 _reflns_number_gt 2262 _reflns_number_total 2287 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd3012.cif 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' 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' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy N N1 0.20032(9) 0.17468(12) 0.40450(5) 0.01045(16) Uani d 1 C C11 0.02801(10) 0.25259(15) 0.40099(5) 0.01133(17) Uani d 1 H H11A -0.0418(17) 0.134(2) 0.3818(9) 0.016(3) Uiso d 1 H H11B -0.0029(16) 0.298(2) 0.4575(8) 0.015(3) Uiso d 1 C C12 0.00604(10) 0.43807(14) 0.33698(5) 0.01108(17) Uani d 1 O O12 0.09113(8) 0.44495(11) 0.27405(4) 0.01392(16) Uani d 1 N N12 -0.11265(10) 0.58350(14) 0.35248(5) 0.01517(17) Uani d 1 H H12A -0.1341(19) 0.690(3) 0.3143(10) 0.024(4) Uiso d 1 H H12B -0.167(2) 0.573(3) 0.3995(11) 0.034(4) Uiso d 1 C C2 0.31875(10) 0.30289(14) 0.44480(5) 0.00998(17) Uani d 1 O O2 0.28183(8) 0.47192(11) 0.48271(4) 0.01277(15) Uani d 1 N N3 0.48048(8) 0.23458(12) 0.44053(5) 0.01036(16) Uani d 1 H H3 0.5603(19) 0.322(3) 0.4685(9) 0.025(4) Uiso d 1 C C4 0.53446(10) 0.04796(14) 0.39965(5) 0.01024(17) Uani d 1 O O4 0.68339(8) 0.00082(12) 0.40276(4) 0.01429(16) Uani d 1 C C5 0.40329(10) -0.07795(14) 0.35600(5) 0.01090(17) Uani d 1 C C51 0.45245(11) -0.27430(15) 0.30725(6) 0.01506(18) Uani d 1 H H51A 0.5310(19) -0.232(3) 0.2654(10) 0.026(4) Uiso d 1 H H51B 0.5117(18) -0.382(3) 0.3456(9) 0.022(3) Uiso d 1 H H51C 0.3525(19) -0.345(3) 0.2787(9) 0.024(4) Uiso d 1 C C6 0.24417(10) -0.00998(14) 0.36052(5) 0.01097(17) Uani d 1 H H6 0.1519(17) -0.084(2) 0.3324(9) 0.017(3) Uiso d 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0069(3) 0.0115(3) 0.0129(3) -0.0002(2) -0.0003(2) -0.0010(2) C11 0.0061(3) 0.0140(4) 0.0139(4) 0.0004(3) 0.0006(3) 0.0007(3) C12 0.0077(3) 0.0128(4) 0.0126(4) -0.0008(3) -0.0011(3) -0.0009(3) O12 0.0117(3) 0.0171(3) 0.0132(3) 0.0005(2) 0.0025(2) 0.0002(2) N12 0.0124(3) 0.0170(4) 0.0164(4) 0.0046(3) 0.0032(3) 0.0018(3) C2 0.0082(3) 0.0115(4) 0.0102(3) -0.0006(3) 0.0004(3) 0.0014(3) O2 0.0105(3) 0.0125(3) 0.0154(3) -0.0002(2) 0.0013(2) -0.0029(2) N3 0.0069(3) 0.0118(3) 0.0123(3) -0.0009(2) -0.0003(2) -0.0014(2) C4 0.0094(4) 0.0111(4) 0.0104(3) -0.0002(3) 0.0015(3) 0.0016(3) O4 0.0080(3) 0.0168(3) 0.0182(3) 0.0011(2) 0.0017(2) -0.0003(2) C5 0.0105(4) 0.0107(4) 0.0115(3) -0.0007(3) 0.0007(3) 0.0001(3) C51 0.0139(4) 0.0128(4) 0.0186(4) 0.0000(3) 0.0020(3) -0.0037(3) C6 0.0104(4) 0.0110(4) 0.0115(4) -0.0011(3) -0.0007(3) -0.0002(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.3686(11) N1 C6 1.3869(11) N1 C11 1.4640(10) C11 C12 1.5301(12) C11 H11A 0.959(14) C11 H11B 0.981(13) C12 O12 1.2380(10) C12 N12 1.3394(11) N12 H12A 0.901(16) N12 H12B 0.887(17) C2 O2 1.2436(11) C2 N3 1.3711(10) N3 C4 1.3972(11) N3 H3 0.931(16) C4 O4 1.2304(10) C4 C5 1.4542(12) C5 C6 1.3510(11) C5 C51 1.4968(12) C51 H51A 0.974(16) C51 H51B 1.003(15) C51 H51C 1.002(15) C6 H6 0.961(14) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C6 121.13(7) C2 N1 C11 117.62(7) C6 N1 C11 120.86(7) N1 C11 C12 110.24(7) N1 C11 H11A 107.5(8) C12 C11 H11A 108.1(8) N1 C11 H11B 110.0(8) C12 C11 H11B 111.5(8) H11A C11 H11B 109.5(11) O12 C12 N12 123.56(8) O12 C12 C11 120.60(8) N12 C12 C11 115.80(7) C12 N12 H12A 118.4(10) C12 N12 H12B 119.7(11) H12A N12 H12B 122.0(15) O2 C2 N1 121.93(8) O2 C2 N3 122.00(8) N1 C2 N3 116.07(7) C2 N3 C4 126.30(7) C2 N3 H3 115.6(10) C4 N3 H3 118.1(10) O4 C4 N3 119.96(8) O4 C4 C5 125.04(8) N3 C4 C5 115.00(7) C6 C5 C4 118.40(8) C6 C5 C51 123.53(8) C4 C5 C51 118.06(7) C5 C51 H51A 109.3(9) C5 C51 H51B 110.5(9) H51A C51 H51B 106.7(12) C5 C51 H51C 110.9(9) H51A C51 H51C 110.1(12) H51B C51 H51C 109.4(12) C5 C6 N1 123.05(8) C5 C6 H6 122.6(8) N1 C6 H6 114.3(8) 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 C2 N1 C11 C12 74.19(9) C6 N1 C11 C12 -98.82(9) N1 C11 C12 O12 30.62(11) N1 C11 C12 N12 -151.50(8) C6 N1 C2 O2 178.17(8) C11 N1 C2 O2 5.18(12) C6 N1 C2 N3 -1.52(12) C11 N1 C2 N3 -174.50(7) O2 C2 N3 C4 -179.99(8) N1 C2 N3 C4 -0.31(12) C2 N3 C4 O4 -177.66(8) C2 N3 C4 C5 2.01(12) O4 C4 C5 C6 177.72(8) N3 C4 C5 C6 -1.93(11) O4 C4 C5 C51 -3.23(13) N3 C4 C5 C51 177.12(7) C4 C5 C6 N1 0.31(13) C51 C5 C6 N1 -178.68(8) C2 N1 C6 C5 1.53(13) C11 N1 C6 C5 174.29(8) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N3 H3 O2 3_666 0.93(2) 1.93(2) 2.8550(10) 173.0(10) N12 H12B O2 3_566 0.89(2) 2.14(2) 3.0240(10) 175(2) N12 H12A O12 2 0.90(2) 2.14(2) 3.0030(10) 160.0(10) C6 H6 O12 2_545 0.960(10) 2.520(10) 3.3620(10) 146.0(10) C11 H11A O4 1_455 0.960(10) 2.400(10) 3.1750(10) 138.0(10) _cod_database_code 2015358