data_2200266 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o386 _journal_page_last o388 _publ_section_title ; 4-{3-[(4-Fluorobenzylidene)amino]-2-oxo-1,3-oxazolidin-5-ylmethyl}morpholine ; loop_ _publ_author_name 'Kruszynski, Rafal' 'Bartczak, Tadeusz J.' 'Chilmonczyk, Zdzislaw' 'Cybulski, Jacek' _chemical_name_common ; 5-morpholinemethyl-3-(4-fluoridebenzylideamin)-2-oxazolidinone ; _chemical_formula_moiety 'C15 H18 F N3 O3' _chemical_formula_sum 'C15 H18 F N3 O3' _chemical_formula_iupac 'C15 H18 F N3 O3' _chemical_formula_weight 307.32 _chemical_melting_point '432.6-433.5 K' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4808(7) _cell_length_b 9.9636(9) _cell_length_c 12.2753(11) _cell_angle_alpha 91.600(9) _cell_angle_beta 101.048(10) _cell_angle_gamma 106.114(12) _cell_volume 744.62(12) _cell_formula_units_Z 2 _cell_measurement_temperature 291.0(10) _exptl_crystal_density_diffrn 1.371 _diffrn_ambient_temperature 291.0(10) 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 C1 -.1389(5) .2692(3) .8864(3) .0623(8) Uani d . 1 . . C H1A -.0254 .3475 .9298 .075 Uiso calc R 1 . . H H1B -.0816 .2375 .8263 .075 Uiso calc R 1 . . H C2 -.2009(6) .1533(4) .9585(3) .0730(10) Uani d . 1 . . C H2A -.3082 .0735 .9136 .088 Uiso calc R 1 . . H H2B -.0722 .1244 .9895 .088 Uiso calc R 1 . . H O1 -.2894(5) .1940(3) 1.04620(19) .0946(9) Uani d . 1 . . O C3 -.4751(6) .2383(5) 1.0036(3) .0888(12) Uani d . 1 . . C H3A -.5300 .2694 1.0649 .107 Uiso calc R 1 . . H H3B -.5898 .1597 .9613 .107 Uiso calc R 1 . . H C4 -.4230(6) .3549(4) .9303(3) .0799(11) Uani d . 1 . . C H4A -.5557 .3792 .8991 .096 Uiso calc R 1 . . H H4B -.3193 .4370 .9741 .096 Uiso calc R 1 . . H N1 -.3302(4) .3137(3) .8410(2) .0657(8) Uani d . 1 . . N C5A -.2649(9) .4568(6) .7954(5) .0528(19) Uani d P .571(9) A 1 C H5A1 -.3910 .4928 .7786 .063 Uiso calc PR .571(9) A 1 H H5A2 -.1519 .5225 .8505 .063 Uiso calc PR .571(9) A 1 H C6A -.1805(9) .4409(8) .6916(6) .0491(16) Uani d P .571(9) A 1 C H6A -.2449 .3476 .6515 .059 Uiso calc PR .571(9) A 1 H C5B -.3304(10) .3687(8) .7263(6) .045(2) Uani d P .429(9) A 2 C H5B1 -.2970 .3029 .6775 .054 Uiso calc PR .429(9) A 2 H H5B2 -.4752 .3763 .6944 .054 Uiso calc PR .429(9) A 2 H C6B -.1636(12) .5100(11) .7339(7) .046(2) Uani d P .429(9) A 2 C H6B -.1574 .5756 .7962 .055 Uiso calc PR .429(9) A 2 H C8 -.2067(4) .5637(4) .6167(3) .0633(9) Uani d . 1 . . C H8A -.3040 .5281 .5452 .076 Uiso calc R 1 B 1 H H8B -.2615 .6300 .6535 .076 Uiso calc R 1 B 1 H N2 .0155(4) .6262(3) .6047(2) .0643(8) Uani d . 1 . . N C7 .1620(4) .5715(3) .6681(3) .0596(8) Uani d . 1 . . C O2 .0568(3) .4768(2) .72964(19) .0747(7) Uani d . 1 . . O O3 .3540(3) .5969(3) .6704(2) .0831(8) Uani d . 1 . . O N3 .0861(4) .7241(2) .53426(19) .0532(6) Uani d . 1 . . N C9 -.0568(4) .7691(3) .4718(2) .0491(7) Uani d . 1 . . C H9 -.2045 .7331 .4739 .059 Uiso calc R 1 . . H C10 .0094(4) .8765(3) .3973(2) .0445(6) Uani d . 1 . . C C11 .2295(4) .9442(3) .4010(2) .0531(7) Uani d . 1 . . C H11 .3366 .9191 .4512 .064 Uiso calc R 1 . . H C12 .2925(5) 1.0474(3) .3320(2) .0591(8) Uani d . 1 . . C H12 .4401 1.0926 .3351 .071 Uiso calc R 1 . . H C13 .1316(5) 1.0815(3) .2588(2) .0589(8) Uani d . 1 . . C C14 -.0859(5) 1.0196(3) .2522(2) .0593(8) Uani d . 1 . . C H14 -.1910 1.0461 .2017 .071 Uiso calc R 1 . . H C15 -.1475(5) .9160(3) .3225(2) .0548(7) Uani d . 1 . . C H15 -.2956 .8726 .3194 .066 Uiso calc R 1 . . H F1 .1919(3) 1.1824(2) .18925(16) .0858(7) Uani d . 1 . . F 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 C1 .0587(18) .0667(19) .071(2) .0278(15) .0198(15) .0281(16) C2 .096(2) .079(2) .061(2) .0444(19) .0280(18) .0310(18) O1 .112(2) .139(2) .0575(14) .0628(18) .0329(14) .0357(15) C3 .093(3) .120(3) .073(2) .042(2) .045(2) .028(2) C4 .065(2) .071(2) .118(3) .0304(18) .036(2) .016(2) N1 .0506(14) .0818(18) .0805(18) .0293(13) .0302(13) .0502(15) C5A .054(3) .058(4) .054(4) .023(3) .017(3) .018(3) C6A .040(3) .057(4) .056(4) .020(3) .015(3) .015(3) C5B .034(3) .048(4) .050(4) .005(3) .009(3) .019(4) C6B .039(4) .057(6) .049(5) .016(4) .023(3) .018(4) C8 .0394(15) .093(2) .0670(19) .0227(15) .0223(13) .0443(17) N2 .0390(12) .0868(18) .0774(17) .0229(12) .0237(12) .0490(15) C7 .0424(16) .070(2) .074(2) .0199(14) .0203(14) .0348(16) O2 .0434(11) .0971(17) .0905(16) .0219(11) .0206(11) .0588(14) O3 .0381(11) .1048(18) .118(2) .0279(11) .0257(12) .0564(16) N3 .0481(13) .0596(14) .0585(14) .0158(11) .0231(11) .0270(12) C9 .0430(14) .0587(17) .0496(15) .0152(12) .0167(12) .0150(13) C10 .0484(14) .0470(15) .0390(14) .0126(12) .0125(11) .0090(12) C11 .0499(16) .0579(17) .0482(16) .0103(13) .0089(12) .0128(13) C12 .0543(17) .0582(18) .0594(18) .0041(14) .0151(14) .0151(15) C13 .076(2) .0518(17) .0488(16) .0112(15) .0219(15) .0180(14) C14 .0657(18) .0637(19) .0520(17) .0229(15) .0119(14) .0211(15) C15 .0496(16) .0610(18) .0560(17) .0171(13) .0130(13) .0157(14) F1 .1029(15) .0773(13) .0717(12) .0103(11) .0236(11) .0387(11) 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 C1 N1 . 1.448(3) no C1 C2 . 1.488(4) no C1 H1A . .9700 no C1 H1B . .9700 no C2 O1 . 1.412(4) no C2 H2A . .9700 no C2 H2B . .9700 no O1 C3 . 1.409(4) no C3 C4 . 1.493(5) no C3 H3A . .9700 no C3 H3B . .9700 no C4 N1 . 1.448(4) no C4 H4A . .9700 no C4 H4B . .9700 no N1 C5B . 1.525(6) no N1 C5A . 1.525(6) no C5A C6A . 1.501(10) no C5A H5A1 . .9700 no C5A H5A2 . .9700 no C6A O2 . 1.457(6) no C6A C8 . 1.578(6) no C6A H6A . .9800 no C5B C6B . 1.506(13) no C5B H5B1 . .9700 no C5B H5B2 . .9700 no C6B C8 . 1.551(8) no C6B O2 . 1.563(8) no C6B H6B . .9800 no C8 N2 . 1.440(3) no C8 H8A . .9700 no C8 H8B . .9700 no N2 C7 . 1.353(3) no N2 N3 . 1.363(3) no C7 O3 . 1.193(3) no C7 O2 . 1.344(3) no N3 C9 . 1.275(3) no C9 C10 . 1.455(3) no C9 H9 . .9300 no C10 C15 . 1.384(4) no C10 C11 . 1.390(4) no C11 C12 . 1.374(4) no C11 H11 . .9300 no C12 C13 . 1.366(4) no C12 H12 . .9300 no C13 C14 . 1.358(4) no C13 F1 . 1.360(3) no C14 C15 . 1.387(4) no C14 H14 . .9300 no C15 H15 . .9300 no