#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/53/2015312.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_2015312 loop_ _publ_author_name 'Torre, Jos\'e M. de la' 'Nogueras, Manuel' 'Cobo, Justo' 'Low, John N.' 'Glidewell, Christopher' _publ_section_title ; N-(2-Methoxy-6-oxo-1,6-dihydropyrimidin-4-yl)formamide: hydrogen-bonded sheets of centrosymmetric R~2~^2^(8) and R~6~^4^(28) rings ; _journal_coeditor_code GG3008 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o256 _journal_page_last o258 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C6 H7 N3 O3' _chemical_formula_moiety 'C6 H7 N3 O3' _chemical_formula_sum 'C6 H7 N3 O3' _chemical_formula_weight 169.15 _chemical_name_systematic ; N-(2-Methoxy-6-oxopyrimidin-4-yl)formamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.690(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.0515(7) _cell_length_b 9.0031(12) _cell_length_c 11.237(2) _cell_measurement_reflns_used 1627 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.52 _cell_measurement_theta_min 5.04 _cell_volume 711.91(17) _computing_cell_refinement 'DIRAX (Duisenberg, 1992)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 9104 _diffrn_reflns_theta_full 27.52 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 5.04 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(EvalCCD; Duisenberg et al., 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.410 _refine_diff_density_min -0.387 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 1627 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.105 _refine_ls_R_factor_all 0.1286 _refine_ls_R_factor_gt 0.0511 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0612P)^2^+0.3784P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1100 _refine_ls_wR_factor_ref 0.1465 _reflns_number_gt 905 _reflns_number_total 1627 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gg3008.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2015312 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x+1/2, -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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N N1 0.3014(3) 0.0726(2) 0.55912(17) 0.0187(5) Uani d . 1 . . C C2 0.3736(3) 0.1943(3) 0.6021(2) 0.0171(6) Uani d . 1 . . O O2 0.4187(2) 0.21160(19) 0.71744(14) 0.0221(5) Uani d . 1 . . C C21 0.3896(4) 0.0828(3) 0.7918(2) 0.0236(6) Uani d . 1 . . N N3 0.4128(3) 0.3157(2) 0.53714(17) 0.0183(5) Uani d . 1 . . C C4 0.3762(3) 0.3182(3) 0.4151(2) 0.0181(6) Uani d . 1 . . O O4 0.4137(2) 0.43389(18) 0.35866(14) 0.0212(5) Uani d . 1 . . C C5 0.2965(3) 0.1873(3) 0.3653(2) 0.0180(6) Uani d . 1 . . C C6 0.2627(3) 0.0717(3) 0.4385(2) 0.0170(6) Uani d . 1 B . N N6 0.1828(3) -0.0589(2) 0.39260(17) 0.0187(5) Uani d . 1 . . C C61 0.1397(4) -0.1787(3) 0.4596(2) 0.0205(6) Uani d . 1 B -2 O O6 0.0661(3) -0.29016(19) 0.41713(15) 0.0268(5) Uani d . 1 B -2 H H21A 0.4277 0.1066 0.8750 0.035 Uiso calc R 1 . . H H21B 0.4664 -0.0002 0.7654 0.035 Uiso calc R 1 . . H H21C 0.2550 0.0549 0.7852 0.035 Uiso calc R 1 . . H H3 0.4625 0.3946 0.5734 0.022 Uiso calc R 1 . . H H5 0.2668 0.1800 0.2819 0.022 Uiso calc R 1 . . H H6 0.1525 -0.0644 0.3156 0.022 Uiso d PR 0.73(5) A -1 H H6A 0.1241 -0.0700 0.2616 0.022 Uiso d PR 0.27(5) A -2 H H61 0.1684 -0.1749 0.5433 0.025 Uiso calc R 1 B -2 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 0.0206(11) 0.0190(12) 0.0160(11) -0.0007(9) -0.0013(8) -0.0012(9) C2 0.0160(13) 0.0187(14) 0.0164(12) 0.0017(11) 0.0005(10) -0.0007(10) O2 0.0306(10) 0.0214(10) 0.0138(9) -0.0033(8) -0.0016(7) 0.0011(7) C21 0.0305(15) 0.0242(15) 0.0160(13) -0.0019(12) 0.0011(11) 0.0025(11) N3 0.0239(12) 0.0152(12) 0.0156(11) -0.0028(9) -0.0012(9) -0.0003(8) C4 0.0161(13) 0.0218(14) 0.0165(12) 0.0012(11) 0.0022(10) 0.0005(11) O4 0.0290(10) 0.0166(10) 0.0178(9) -0.0028(8) -0.0009(7) 0.0022(7) C5 0.0205(14) 0.0194(14) 0.0136(12) -0.0001(11) -0.0016(10) -0.0001(10) C6 0.0146(13) 0.0210(14) 0.0155(12) 0.0030(11) 0.0000(9) -0.0027(11) N6 0.0249(12) 0.0164(12) 0.0147(10) -0.0010(10) 0.0001(8) -0.0014(9) C61 0.0249(14) 0.0198(15) 0.0170(13) 0.0017(12) 0.0040(11) -0.0005(11) O6 0.0339(11) 0.0208(11) 0.0256(10) -0.0061(9) 0.0022(8) -0.0030(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.289(3) y C2 N3 1.353(3) y N3 C4 1.379(3) y C4 C5 1.406(3) y C5 C6 1.357(3) y C6 N1 1.365(3) y C2 O2 1.324(3) y O2 C21 1.452(3) y C4 O4 1.257(3) y C6 N6 1.389(3) y N6 C61 1.361(3) y C61 O6 1.213(3) y C21 H21A 0.98 no C21 H21B 0.98 no C21 H21C 0.98 no N3 H3 0.88 no C5 H5 0.95 no N6 H6 0.88 no N6 H6A 1.51 no C61 H61 0.95 no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 N1 C6 115.2(2) no N1 C2 O2 122.1(2) no N1 C2 N3 125.1(2) no O2 C2 N3 112.8(2) no C2 O2 C21 115.79(19) no O2 C21 H21A 109.5 no O2 C21 H21B 109.5 no H21A C21 H21B 109.5 no O2 C21 H21C 109.5 no H21A C21 H21C 109.5 no H21B C21 H21C 109.5 no C2 N3 C4 121.2(2) no C2 N3 H3 119.4 no C4 N3 H3 119.4 no O4 C4 N3 118.9(2) no O4 C4 C5 125.8(2) no N3 C4 C5 115.3(2) no C6 C5 C4 118.9(2) no C6 C5 H5 120.6 no C4 C5 H5 120.6 no C5 C6 N1 124.4(2) no C5 C6 N6 120.4(2) no N1 C6 N6 115.1(2) no C61 N6 C6 124.4(2) no C61 N6 H6 116.8 no C6 N6 H6 118.7 no C61 N6 H6A 115.5 no C6 N6 H6A 119.9 no O6 C61 N6 122.9(2) no O6 C61 H61 118.5 no N6 C61 H61 118.5 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_publ_flag C6 N1 C2 O2 -179.9(2) no C6 N1 C2 N3 -0.4(4) no N1 C2 O2 C21 2.6(3) no N3 C2 O2 C21 -176.9(2) no N1 C2 N3 C4 0.2(4) no O2 C2 N3 C4 179.7(2) no C2 N3 C4 O4 179.5(2) no C2 N3 C4 C5 0.1(3) no O4 C4 C5 C6 -179.5(2) no N3 C4 C5 C6 -0.1(3) no C4 C5 C6 N1 -0.2(4) no C4 C5 C6 N6 179.5(2) no C2 N1 C6 C5 0.4(4) no C2 N1 C6 N6 -179.3(2) no C5 C6 N6 C61 -178.2(2) no N1 C6 N6 C61 1.5(3) y C6 N6 C61 O6 178.4(2) y 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 _geom_hbond_publ_flag N3 H3 O4 3_666 0.88 1.91 2.786(3) 175 y N6 H6 O4 2_545 0.88 1.98 2.862(3) 177 y N6 H6A O4 2_545 1.51 1.36 2.862(3) 173 no