#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/46/2204649.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_2204649 loop_ _publ_author_name 'Dege, Necmi' '\,Sekerci, Memet' '\,Cetin, Ahmet' 'Din\,cer, Muharrem' 'G\"ulcan, Mehmet' 'Cans\?iz, Ahmet' 'B\"uy\"ukg\"ung\"or, Orhan' _publ_section_title ; 1-Amino-5-benzoyl-4-phenylpyrimidin-2(1H)-one ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2476 _journal_page_last o2478 _journal_paper_doi 10.1107/S1600536804030338 _journal_volume 60 _journal_year 2004 _chemical_formula_moiety 'C17 H13 N3 O2' _chemical_formula_sum 'C17 H13 N3 O2' _chemical_formula_weight 291.30 _chemical_name_systematic ; 1-amino-5-benzoyl-4-phenylpyrimidin-2(1H)-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/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 101.722(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.7547(11) _cell_length_b 16.6566(11) _cell_length_c 7.2986(6) _cell_measurement_reflns_used 10310 _cell_measurement_temperature 296 _cell_measurement_theta_max 28.91 _cell_measurement_theta_min 1.77 _cell_volume 1399.2(2) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296 _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'STOE IPDS-II' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_source 'sealed X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 9982 _diffrn_reflns_theta_full 28.78 _diffrn_reflns_theta_max 28.78 _diffrn_reflns_theta_min 1.77 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.146 _refine_diff_density_min -0.127 _refine_ls_extinction_coef 0.033(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 1.038 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 252 _refine_ls_number_reflns 3605 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0373 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+0.0428P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0977 _refine_ls_wR_factor_ref 0.1047 _reflns_number_gt 2612 _reflns_number_total 3605 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file ci6491.cif _cod_data_source_block V _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2204649 _cod_database_fobs_code 2204649 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_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 _atom_site_type_symbol N1 0.58123(8) 0.17479(6) 0.02078(14) 0.0448(2) Uani d 1 N N2 0.50825(8) 0.11459(6) 0.26760(14) 0.0421(2) Uani d 1 N N3 0.43127(10) 0.11393(7) 0.39451(17) 0.0506(3) Uani d 1 N H3A 0.3604(16) 0.1057(9) 0.321(2) 0.070(5) Uiso d 1 H H3B 0.4333(15) 0.1657(12) 0.445(3) 0.081(5) Uiso d 1 H O1 0.42618(8) 0.22736(5) 0.12324(14) 0.0561(3) Uani d 1 O O2 0.72262(9) -0.05651(5) -0.01925(12) 0.0572(3) Uani d 1 O C1 0.85852(11) 0.10648(8) -0.0205(2) 0.0522(3) Uani d 1 C H1C 0.8822(13) 0.0837(9) 0.103(2) 0.063(4) Uiso d 1 H C2 0.94163(13) 0.12410(10) -0.1242(2) 0.0629(4) Uani d 1 C H2C 1.0232(18) 0.1119(10) -0.077(3) 0.081(5) Uiso d 1 H C3 0.90939(14) 0.15934(9) -0.2974(2) 0.0663(4) Uani d 1 C H3C 0.9649(17) 0.1718(11) -0.371(3) 0.092(6) Uiso d 1 H C4 0.79406(15) 0.17706(8) -0.3692(2) 0.0616(4) Uani d 1 C H4C 0.7692(14) 0.2029(10) -0.490(3) 0.073(5) Uiso d 1 H C5 0.71059(12) 0.16006(7) -0.26599(19) 0.0508(3) Uani d 1 C H5C 0.6316(13) 0.1735(8) -0.3113(19) 0.050(4) Uiso d 1 H C6 0.74220(10) 0.12465(7) -0.09104(17) 0.0429(3) Uani d 1 C C7 0.65388(9) 0.11461(6) 0.02669(16) 0.0402(2) Uani d 1 C C8 0.50037(9) 0.17586(7) 0.13203(17) 0.0429(3) Uani d 1 C C9 0.58059(10) 0.05214(7) 0.27156(17) 0.0419(3) Uani d 1 C H9C 0.5739(11) 0.0104(8) 0.3658(19) 0.045(3) Uiso d 1 H C10 0.65380(9) 0.04737(7) 0.14822(16) 0.0404(2) Uani d 1 C C11 0.71652(10) -0.02907(6) 0.13330(16) 0.0413(2) Uani d 1 C C12 0.76959(9) -0.07185(6) 0.30807(16) 0.0391(2) Uani d 1 C C13 0.76558(10) -0.15524(7) 0.31283(18) 0.0440(3) Uani d 1 C H13C 0.7241(12) -0.1846(8) 0.203(2) 0.051(4) Uiso d 1 H C14 0.81859(11) -0.19559(7) 0.4731(2) 0.0503(3) Uani d 1 C H14C 0.8149(12) -0.2545(9) 0.479(2) 0.059(4) Uiso d 1 H C15 0.87739(12) -0.15385(8) 0.6260(2) 0.0548(3) Uani d 1 C H15C 0.9159(14) -0.1825(9) 0.738(2) 0.068(4) Uiso d 1 H C16 0.88069(12) -0.07113(9) 0.6228(2) 0.0562(3) Uani d 1 C H16C 0.9220(15) -0.0405(10) 0.730(2) 0.074(5) Uiso d 1 H C17 0.82607(11) -0.02995(7) 0.46508(18) 0.0487(3) Uani d 1 C H17C 0.8269(12) 0.0291(9) 0.4603(19) 0.057(4) Uiso d 1 H 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 0.0394(5) 0.0473(5) 0.0490(6) 0.0059(4) 0.0119(4) 0.0048(4) N2 0.0365(5) 0.0478(5) 0.0435(5) 0.0050(4) 0.0118(4) 0.0021(4) N3 0.0438(6) 0.0620(7) 0.0504(6) 0.0060(5) 0.0196(5) 0.0008(5) O1 0.0490(5) 0.0571(5) 0.0648(6) 0.0180(4) 0.0173(4) 0.0079(4) O2 0.0740(6) 0.0534(5) 0.0454(5) 0.0046(4) 0.0152(4) -0.0068(4) C1 0.0404(6) 0.0599(7) 0.0572(8) -0.0018(5) 0.0118(6) -0.0020(6) C2 0.0451(7) 0.0721(9) 0.0758(10) -0.0078(6) 0.0223(7) -0.0127(8) C3 0.0684(9) 0.0642(8) 0.0779(10) -0.0170(7) 0.0421(8) -0.0128(7) C4 0.0838(10) 0.0522(7) 0.0562(8) -0.0032(7) 0.0315(8) 0.0008(6) C5 0.0563(7) 0.0486(6) 0.0502(7) 0.0048(5) 0.0171(6) 0.0031(5) C6 0.0420(6) 0.0410(5) 0.0476(6) -0.0011(4) 0.0134(5) -0.0021(5) C7 0.0351(5) 0.0435(6) 0.0412(6) 0.0008(4) 0.0058(4) -0.0001(4) C8 0.0372(5) 0.0450(6) 0.0460(6) 0.0042(4) 0.0072(5) 0.0016(5) C9 0.0386(5) 0.0451(6) 0.0423(6) 0.0030(4) 0.0089(5) 0.0024(5) C10 0.0358(5) 0.0437(5) 0.0418(6) 0.0024(4) 0.0078(4) 0.0005(4) C11 0.0392(5) 0.0422(5) 0.0436(6) -0.0010(4) 0.0114(5) -0.0030(5) C12 0.0346(5) 0.0402(5) 0.0444(6) 0.0027(4) 0.0121(4) -0.0013(4) C13 0.0426(6) 0.0409(5) 0.0513(7) -0.0003(4) 0.0164(5) -0.0025(5) C14 0.0506(6) 0.0433(6) 0.0613(8) 0.0030(5) 0.0218(6) 0.0080(5) C15 0.0504(7) 0.0618(8) 0.0529(8) 0.0086(6) 0.0122(6) 0.0115(6) C16 0.0542(7) 0.0609(8) 0.0495(8) 0.0048(6) 0.0010(6) -0.0029(6) C17 0.0491(6) 0.0421(6) 0.0528(7) 0.0030(5) 0.0055(5) -0.0042(5) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C7 N1 C8 121.05(10) ? C9 N2 C8 121.83(10) yes C9 N2 N3 117.73(10) yes C8 N2 N3 120.20(9) ? N2 N3 H3A 104.2(11) ? N2 N3 H3B 106.3(11) ? H3A N3 H3B 108.6(15) ? C2 C1 C6 120.07(14) ? C2 C1 H1C 119.5(9) ? C6 C1 H1C 120.4(9) ? C3 C2 C1 120.00(14) ? C3 C2 H2C 118.9(11) ? C1 C2 H2C 121.1(11) ? C2 C3 C4 120.38(13) ? C2 C3 H3C 121.3(12) ? C4 C3 H3C 118.3(12) ? C5 C4 C3 119.97(15) ? C5 C4 H4C 117.9(10) ? C3 C4 H4C 122.1(10) ? C4 C5 C6 120.11(13) ? C4 C5 H5C 121.0(8) ? C6 C5 H5C 118.8(8) ? C5 C6 C1 119.46(11) ? C5 C6 C7 119.50(11) ? C1 C6 C7 120.72(11) ? N1 C7 C10 122.47(10) ? N1 C7 C6 114.95(10) ? C10 C7 C6 122.41(10) ? O1 C8 N1 123.68(11) yes O1 C8 N2 119.44(11) yes N1 C8 N2 116.84(9) ? N2 C9 C10 120.80(11) ? N2 C9 H9C 114.8(7) ? C10 C9 H9C 124.4(7) ? C9 C10 C7 116.27(10) y C9 C10 C11 119.06(10) ? C7 C10 C11 124.27(10) y O2 C11 C12 120.85(10) ? O2 C11 C10 120.68(11) yes C12 C11 C10 118.46(9) yes C17 C12 C13 119.60(11) ? C17 C12 C11 120.98(10) ? C13 C12 C11 119.39(10) ? C14 C13 C12 119.67(12) ? C14 C13 H13C 121.0(8) ? C12 C13 H13C 119.4(8) ? C15 C14 C13 120.43(12) ? C15 C14 H14C 119.3(9) ? C13 C14 H14C 120.2(9) ? C14 C15 C16 120.16(13) ? C14 C15 H15C 120.2(9) ? C16 C15 H15C 119.6(9) ? C15 C16 C17 120.02(13) ? C15 C16 H16C 121.2(10) ? C17 C16 H16C 118.7(10) ? C16 C17 C12 120.08(12) ? C16 C17 H17C 121.3(8) ? C12 C17 H17C 118.6(8) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C7 1.3118(14) yes N1 C8 1.3699(15) yes N2 C9 1.3401(14) yes N2 C8 1.4112(15) yes N2 N3 1.4204(13) yes N3 H3A 0.905(18) ? N3 H3B 0.936(19) ? O1 C8 1.2157(13) yes O2 C11 1.2191(14) yes C1 C2 1.3835(19) ? C1 C6 1.3929(17) ? C1 H1C 0.966(16) ? C2 C3 1.375(2) ? C2 H2C 0.97(2) ? C3 C4 1.382(2) ? C3 H3C 0.95(2) ? C4 C5 1.3824(19) ? C4 H4C 0.968(18) ? C5 C6 1.3870(17) ? C5 H5C 0.947(14) ? C6 C7 1.4855(15) yes C7 C10 1.4289(15) ? C9 C10 1.3683(15) ? C9 H9C 0.993(13) ? C10 C11 1.4863(15) yes C11 C12 1.4835(16) yes C12 C17 1.3899(17) ? C12 C13 1.3905(16) ? C13 C14 1.3825(18) ? C13 H13C 0.982(14) ? C14 C15 1.376(2) ? C14 H14C 0.983(15) ? C15 C16 1.379(2) ? C15 H15C 0.975(17) ? C16 C17 1.3814(19) ? C16 H16C 0.979(17) ? C17 H17C 0.984(15) ? 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 H3A O2 3_655 0.91(2) 2.37(2) 3.110(2) 140.0(10) N3 H3B O1 4_566 0.92(2) 2.22(2) 3.134(2) 166(2) N3 H3A CgP 3_656 0.91(2) 2.90(2) 3.3410(10) 112.0(10) C3 H3C CgP 3_755 0.95(2) 2.90(2) 3.692(2) 142(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_publ_flag C6 C1 C2 C3 -0.2(2) ? C1 C2 C3 C4 -0.3(2) ? C2 C3 C4 C5 0.6(2) ? C3 C4 C5 C6 -0.5(2) ? C4 C5 C6 C1 0.04(18) ? C4 C5 C6 C7 173.57(11) ? C2 C1 C6 C5 0.33(19) ? C2 C1 C6 C7 -173.12(12) ? C8 N1 C7 C10 -0.24(17) ? C8 N1 C7 C6 -175.58(10) ? C5 C6 C7 N1 -38.95(15) ? C1 C6 C7 N1 134.50(12) y C5 C6 C7 C10 145.71(12) y C1 C6 C7 C10 -40.84(17) ? C7 N1 C8 O1 -174.93(11) ? C7 N1 C8 N2 7.36(16) ? C9 N2 C8 O1 173.33(11) ? N3 N2 C8 O1 -0.98(17) ? C9 N2 C8 N1 -8.86(16) ? N3 N2 C8 N1 176.83(10) ? C8 N2 C9 C10 2.95(17) ? N3 N2 C9 C10 177.40(11) ? N2 C9 C10 C7 4.23(16) ? N2 C9 C10 C11 -168.85(11) ? N1 C7 C10 C9 -5.75(17) ? C6 C7 C10 C9 169.24(10) ? N1 C7 C10 C11 166.92(11) ? C6 C7 C10 C11 -18.09(17) ? C9 C10 C11 O2 135.53(12) yes C7 C10 C11 O2 -36.96(17) yes C9 C10 C11 C12 -43.39(15) ? C7 C10 C11 C12 144.13(11) ? O2 C11 C12 C17 140.80(12) yes C10 C11 C12 C17 -40.29(15) yes O2 C11 C12 C13 -37.33(16) ? C10 C11 C12 C13 141.58(11) ? C17 C12 C13 C14 -0.52(17) ? C11 C12 C13 C14 177.63(10) ? C12 C13 C14 C15 -1.46(18) ? C13 C14 C15 C16 2.1(2) ? C14 C15 C16 C17 -0.8(2) ? C15 C16 C17 C12 -1.2(2) ? C13 C12 C17 C16 1.86(18) ? C11 C12 C17 C16 -176.27(11) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 10592139 2 PubChem 14472001