#------------------------------------------------------------------------------ #$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $ #$Revision: 14 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013901.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_2013901 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2004 _journal_volume 60 _journal_page_first o232 _journal_page_last o234 _publ_section_title ; 3-[4-(4-Fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one and 3-[4-(2-fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one ; loop_ _publ_author_name 'Yavuz K\"oysal' '\,Samil I\,s\?ik' 'Meri\,c K\"oksal' 'Hakk\?i Erdo\~gan' 'Nesrin Gokhan' _chemical_formula_moiety 'C19 H20 F N3 O2' _chemical_formula_sum 'C19 H20 F N3 O2' _chemical_formula_iupac 'C19 H20 F N3 O2' _chemical_formula_weight 341.22 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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' _cell_length_a 8.1788(6) _cell_length_b 6.1512(4) _cell_length_c 34.090(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.067(7) _cell_angle_gamma 90.00 _cell_volume 1670.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.357 _diffrn_ambient_temperature 293(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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol F1 -0.4451(3) 0.1980(4) 0.25278(8) 0.0883(8) Uani d . 1 . . F O1 0.6376(4) 0.7349(5) 0.11743(9) 0.0921(9) Uani d . 1 . . O O2 0.5004(3) 0.8047(3) 0.05353(7) 0.0634(6) Uani d . 1 . . O N1 0.0705(3) 0.2670(4) 0.17372(9) 0.0623(7) Uani d . 1 . . N N2 0.3002(4) 0.3067(4) 0.12303(9) 0.0709(9) Uani d . 1 . . N N3 0.4476(3) 0.4915(4) 0.08023(7) 0.0523(6) Uani d . 1 . . N C1 -0.3220(4) 0.2157(6) 0.23245(11) 0.0624(8) Uani d . 1 . . C C2 -0.2266(4) 0.4004(6) 0.23707(11) 0.0661(9) Uani d . 1 . . C H2 -0.2467 0.5116 0.2538 0.076(11) Uiso d R 1 . . H C3 -0.0995(4) 0.4168(5) 0.21697(11) 0.0613(8) Uani d . 1 . . C H3 -0.0336 0.5416 0.2201 0.064(9) Uiso d R 1 . . H C4 -0.0671(3) 0.2523(4) 0.19178(9) 0.0512(7) Uani d . 1 . . C C5 -0.1692(4) 0.0694(5) 0.18714(10) 0.0584(8) Uani d . 1 . . C H5 -0.1527 -0.0418 0.1700 0.065(9) Uiso d R 1 . . H C6 -0.2963(4) 0.0526(6) 0.20758(11) 0.0661(9) Uani d . 1 . . C H6 -0.3639 -0.0705 0.2046 0.087(12) Uiso d R 1 . . H C7 0.1183(6) 0.4709(6) 0.16319(14) 0.0859(13) Uani d . 1 . . C H7A 0.1208 0.5700 0.1855 0.103 Uiso calc R 1 . . H H7B 0.0347 0.5239 0.1403 0.103 Uiso calc R 1 . . H C8 0.2901(5) 0.4735(5) 0.15245(11) 0.0641(9) Uani d . 1 . . C H8A 0.3007 0.6150 0.1408 0.077(11) Uiso d R 1 . . H H8B 0.3821 0.4572 0.1757 0.123(18) Uiso d R 1 . . H C9 0.2595(6) 0.1032(6) 0.13649(16) 0.0903(13) Uani d . 1 . . C H9A 0.3419 0.0649 0.1607 0.108 Uiso calc R 1 . . H H9B 0.2652 -0.0049 0.1161 0.108 Uiso calc R 1 . . H C10 0.0904(4) 0.0975(5) 0.14518(11) 0.0650(9) Uani d . 1 . . C H10A 0.0009 0.1073 0.1216 0.093(13) Uiso d R 1 . . H H10B 0.0827 -0.0417 0.1574 0.085(12) Uiso d R 1 . . H C11 0.4556(4) 0.3174(5) 0.10935(10) 0.0619(8) Uani d . 1 . . C H11A 0.4743 0.1801 0.0971 0.064(9) Uiso d R 1 . . H H11B 0.5490 0.3426 0.1321 0.083(12) Uiso d R 1 . . H C12 0.5398(4) 0.6778(5) 0.08766(11) 0.0621(8) Uani d . 1 . . C C13 0.3857(4) 0.6890(4) 0.02439(10) 0.0529(7) Uani d . 1 . . C C14 0.3172(4) 0.7473(5) -0.01371(11) 0.0634(8) Uani d . 1 . . C H14 0.3420 0.8795 -0.0242 0.073(10) Uiso d R 1 . . H C15 0.2082(4) 0.5990(6) -0.03666(11) 0.0641(8) Uani d . 1 . . C H15 0.1585 0.6333 -0.0633 0.068(10) Uiso d R 1 . . H C16 0.1698(4) 0.4003(5) -0.02106(10) 0.0556(7) Uani d . 1 . . C C17 0.2429(3) 0.3473(5) 0.01838(9) 0.0510(7) Uani d . 1 . . C H17 0.2191 0.2157 0.0293 0.054(8) Uiso d R 1 . . H C18 0.3520(3) 0.4937(4) 0.04108(9) 0.0473(6) Uani d . 1 . . C C19 0.0502(4) 0.2464(7) -0.04739(12) 0.0735(10) Uani d . 1 . . C H19A -0.0323 0.3280 -0.0662 0.110 Uiso calc R 1 . . H H19B -0.0047 0.1585 -0.0310 0.110 Uiso calc R 1 . . H H19C 0.1112 0.1545 -0.0618 0.110 Uiso calc R 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 F1 0.0737(13) 0.0909(16) 0.1090(19) 0.0017(11) 0.0390(13) 0.0125(13) O1 0.107(2) 0.0838(19) 0.0788(19) -0.0306(16) 0.0064(15) -0.0247(15) O2 0.0727(14) 0.0458(11) 0.0759(16) -0.0139(10) 0.0258(11) -0.0094(10) N1 0.0670(16) 0.0463(13) 0.0774(19) -0.0094(11) 0.0245(14) -0.0192(12) N2 0.107(2) 0.0521(15) 0.0659(18) -0.0184(15) 0.0459(17) -0.0141(12) N3 0.0636(14) 0.0477(12) 0.0476(13) -0.0058(10) 0.0170(11) -0.0057(10) C1 0.0516(15) 0.0680(19) 0.066(2) 0.0065(14) 0.0096(14) 0.0117(16) C2 0.0610(18) 0.0642(19) 0.074(2) 0.0031(15) 0.0172(16) -0.0077(17) C3 0.0609(17) 0.0521(16) 0.072(2) -0.0044(14) 0.0171(15) -0.0109(15) C4 0.0486(14) 0.0472(14) 0.0533(16) -0.0017(12) 0.0021(12) -0.0038(12) C5 0.0633(17) 0.0474(15) 0.0602(18) -0.0052(13) 0.0049(14) -0.0050(13) C6 0.0591(17) 0.0591(18) 0.076(2) -0.0087(15) 0.0069(16) 0.0037(16) C7 0.129(3) 0.0538(19) 0.094(3) -0.019(2) 0.066(3) -0.0174(18) C8 0.090(2) 0.0450(15) 0.063(2) -0.0118(15) 0.0309(18) -0.0095(14) C9 0.112(3) 0.055(2) 0.116(4) -0.007(2) 0.054(3) -0.020(2) C10 0.080(2) 0.0411(15) 0.078(2) -0.0082(14) 0.0261(18) -0.0144(15) C11 0.078(2) 0.0553(17) 0.0538(18) -0.0006(15) 0.0175(15) -0.0008(13) C12 0.0718(19) 0.0530(16) 0.065(2) -0.0096(14) 0.0229(16) -0.0128(14) C13 0.0553(15) 0.0426(14) 0.0669(19) -0.0001(12) 0.0268(14) -0.0011(13) C14 0.0672(18) 0.0512(16) 0.076(2) 0.0076(14) 0.0251(16) 0.0152(15) C15 0.0628(18) 0.0675(19) 0.0616(19) 0.0128(15) 0.0130(15) 0.0130(16) C16 0.0482(14) 0.0577(16) 0.0614(18) 0.0057(12) 0.0132(12) -0.0028(14) C17 0.0517(14) 0.0449(14) 0.0594(17) -0.0016(12) 0.0190(12) -0.0012(12) C18 0.0492(13) 0.0427(13) 0.0551(16) 0.0010(11) 0.0226(12) -0.0022(11) C19 0.0630(19) 0.078(2) 0.072(2) 0.0016(17) 0.0003(16) -0.0102(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 C1 . 1.350(4) yes O1 C12 . 1.194(4) yes O2 C12 . 1.377(4) yes O2 C13 . 1.397(4) yes N1 C7 . 1.385(4) yes N1 C4 . 1.402(4) yes N1 C10 . 1.460(4) yes N2 C9 . 1.399(5) yes N2 C8 . 1.450(4) yes N2 C11 . 1.451(4) yes N3 C12 . 1.364(4) yes N3 C18 . 1.386(4) yes N3 C11 . 1.452(4) yes C1 C6 . 1.360(5) ? C1 C2 . 1.366(5) ? C2 C3 . 1.372(5) ? C2 H2 . 0.9298 ? C3 C4 . 1.391(4) ? C3 H3 . 0.9299 ? C4 C5 . 1.389(4) ? C5 C6 . 1.380(5) ? C5 H5 . 0.9296 ? C6 H6 . 0.9300 ? C7 C8 . 1.530(5) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 H8A . 0.9680 ? C8 H8B . 0.9661 ? C9 C10 . 1.479(5) ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 H10A . 0.9588 ? C10 H10B . 0.9594 ? C11 H11A . 0.9701 ? C11 H11B . 0.9697 ? C13 C14 . 1.342(5) ? C13 C18 . 1.384(4) ? C14 C15 . 1.387(5) ? C14 H14 . 0.9298 ? C15 C16 . 1.396(5) ? C15 H15 . 0.9301 ? C16 C17 . 1.381(4) ? C16 C19 . 1.504(5) ? C17 C18 . 1.376(4) ? C17 H17 . 0.9299 ? C19 H19A . 0.9600 ? C19 H19B . 0.9600 ? C19 H19C . 0.9600 ?