#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200358.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_2200358 loop_ _publ_author_name 'Kruszynski, Rafal' 'Bartczak, Tadeusz J.' 'Chilmonczyk, Zdzislaw' 'Cybulski, Jacek' _publ_section_title ;4-[3-(4-Fluorobenzylideneamino)-2-oxo-1,3-oxazolidin-5-ylmethyl]morpholin-4-ium chloride monohydrate ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o469 _journal_page_last o471 _journal_paper_doi 10.1107/S1600536801006742 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C15 H19 F N3 O3 1+, Cl 1-, H2 O' _chemical_formula_moiety 'C15 H19 F N3 O3 1+, Cl 1-, H2 O' _chemical_formula_sum 'C15 H21 Cl F N3 O4' _chemical_formula_weight 361.80 _chemical_melting_point 501.6(5) _chemical_name_common ;5-morpholinemethyl-3-(4-fluoridebenzylideamin)-2-oxazolidinone chloride monohydrate ; _chemical_name_systematic ;4-[3-(4-fluorobenzylidenamino)-2-oxooxazolidin-5-ylmethyl]morpholin-4-ium chloride monohydrate ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 104.820(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.9570(9) _cell_length_b 27.968(3) _cell_length_c 7.1370(10) _cell_measurement_reflns_used 99 _cell_measurement_temperature 291.0(10) _cell_measurement_theta_max 60 _cell_measurement_theta_min 5 _cell_volume 1728.4(4) _computing_cell_refinement 'KM-4 Software' _computing_data_collection 'KM-4 Software (Kuma, 1993)' _computing_data_reduction 'DATAPROC (Kuma 1998)' _computing_molecular_graphics ; XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia 1997) ; _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990a)' _diffrn_ambient_temperature 291.0(10) _diffrn_measured_fraction_theta_full .940 _diffrn_measured_fraction_theta_max .940 _diffrn_measurement_device_type 'Kuma KM-4' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54056 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .0170 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3674 _diffrn_reflns_theta_full 81.45 _diffrn_reflns_theta_max 81.45 _diffrn_reflns_theta_min 3.16 _diffrn_standards_decay_% 1.71 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.276 _exptl_absorpt_correction_T_max .6983 _exptl_absorpt_correction_T_min .4705 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details '(X-RED; Stoe & Cie, 1999)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 760 _exptl_crystal_size_max .39 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .17 _refine_diff_density_max .871 _refine_diff_density_min -.423 _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 3674 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.124 _refine_ls_R_factor_all .0835 _refine_ls_R_factor_gt .0629 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1136P)^2^+0.4990P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .2012 _reflns_number_gt 2689 _reflns_number_total 3674 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6015.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '501.2-502.1 K' was changed to '501.6(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '501.2-502.1 K' was changed to '501.6(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2200358 _cod_database_fobs_code 2200358 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 .4961(3) .37889(7) 1.2497(4) .0536(5) Uani d . 1 . . N C4 .6564(3) .37213(11) 1.3677(5) .0672(7) Uani d . 1 . . C H4A .7196 .3979 1.3434 .101 Uiso d R 1 . . H H4B .6574 .3718 1.5025 .101 Uiso d R 1 . . H C3 .7197(4) .32576(12) 1.3176(5) .0752(8) Uani d . 1 . . C H3A .8228 .3217 1.3973 .113 Uiso d R 1 . . H H3B .7216 .3267 1.1838 .113 Uiso d R 1 . . H O1 .6284(3) .28678(8) 1.3449(4) .0831(7) Uani d . 1 . . O C2 .4785(4) .29185(11) 1.2224(6) .0820(10) Uani d . 1 . . C H2A .4857 .2934 1.0906 .123 Uiso d R 1 . . H H2B .4179 .2646 1.2384 .123 Uiso d R 1 . . H C1 .3994(4) .33671(9) 1.2671(5) .0654(7) Uani d . 1 . . C H1A .3871 .3349 1.3967 .098 Uiso d R 1 . . H H1B .2998 .3397 1.1772 .098 Uiso d R 1 . . H C5 .4372(3) .42510(9) 1.3088(4) .0597(6) Uani d . 1 . . C H5A .5114 .4496 1.3052 .090 Uiso d R 1 . . H H5B .4273 .4216 1.4389 .090 Uiso d R 1 . . H C6 .2843(3) .44029(9) 1.1820(4) .0559(6) Uani d . 1 . . C H6 .2817 .4293 1.0538 .084 Uiso d R 1 . . H O2 .1574(2) .42051(6) 1.2498(3) .0595(5) Uani d . 1 . . O C7 .0536(3) .45548(9) 1.2555(4) .0546(6) Uani d . 1 . . C O3 -.0693(2) .44726(7) 1.2881(3) .0688(6) Uani d . 1 . . O N2 .1095(2) .49766(7) 1.2124(3) .0540(5) Uani d . 1 . . N C8 .2657(3) .49440(9) 1.1912(4) .0571(6) Uani d . 1 . . C H8A .2752 .5095 1.0740 .086 Uiso d R 1 . . H H8B .3393 .5081 1.2999 .086 Uiso d R 1 . . H N3 .0318(2) .53915(7) 1.2260(3) .0511(5) Uani d . 1 . . N C9 .1007(3) .57767(8) 1.2022(4) .0520(5) Uani d . 1 . . C H9 .1908 .5764 1.1904 .078 Uiso d R 1 . . H C10 .0335(3) .62494(9) 1.2104(4) .0509(5) Uani d . 1 . . C C11 -.0999(3) .63272(9) 1.2703(4) .0580(6) Uani d . 1 . . C H11 -.1512 .6063 1.3128 .070 Uiso d R 1 . . H C12 -.1591(4) .67820(10) 1.2690(5) .0685(8) Uani d . 1 . . C H12 -.2519 .6837 1.3095 .082 Uiso d R 1 . . H C13 -.0838(4) .71510(10) 1.2095(5) .0690(8) Uani d . 1 . . C C14 .0503(4) .70938(10) 1.1538(5) .0727(8) Uani d . 1 . . C H14 .1018 .7361 1.1138 .087 Uiso d R 1 . . H C15 .1081(3) .66366(9) 1.1551(5) .0630(7) Uani d . 1 . . C H15 .2012 .6618 1.1223 .076 Uiso d R 1 . . H F1 -.1430(3) .75989(6) 1.2068(4) .0998(7) Uani d . 1 . . F Cl1 .50494(8) .39291(3) .82881(11) .0705(3) Uani d . 1 . . Cl O4 .6843(3) .51101(9) 1.3309(4) .0908(8) Uani d . 1 . . O H41 .6610 .5395 1.2889 .136 Uiso d R 1 . . H H42 .7563 .4973 1.2938 .136 Uiso d R 1 . . H H1N .486(3) .3783(10) 1.129(5) .055(8) 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 .0571(12) .0474(10) .0609(13) .0011(8) .0235(10) .0030(9) C4 .0591(15) .0639(16) .0797(19) -.0027(12) .0199(14) -.0039(13) C3 .0697(18) .0774(19) .080(2) .0126(15) .0226(16) .0052(15) O1 .0876(16) .0604(12) .0974(17) .0152(11) .0166(13) .0108(11) C2 .085(2) .0521(15) .107(3) .0010(14) .022(2) -.0083(16) C1 .0662(17) .0505(14) .0836(19) -.0060(11) .0268(15) .0026(12) C5 .0632(15) .0523(13) .0636(15) -.0010(11) .0161(12) -.0054(11) C6 .0587(14) .0528(13) .0597(14) -.0012(11) .0215(12) -.0016(10) O2 .0569(10) .0470(9) .0793(12) -.0006(7) .0260(9) .0026(8) C7 .0532(13) .0506(12) .0615(14) -.0009(10) .0174(11) -.0029(10) O3 .0567(11) .0628(11) .0952(15) -.0075(9) .0345(11) .0000(10) N2 .0495(11) .0471(10) .0691(13) .0014(8) .0220(10) .0013(9) C8 .0538(14) .0510(13) .0727(16) .0015(10) .0276(12) .0040(11) N3 .0517(11) .0467(10) .0560(11) .0021(8) .0158(9) -.0026(8) C9 .0472(12) .0507(12) .0591(14) .0014(9) .0155(10) -.0001(10) C10 .0505(12) .0502(12) .0513(12) .0006(10) .0121(10) -.0016(9) C11 .0535(14) .0525(13) .0708(16) -.0020(10) .0209(12) -.0052(11) C12 .0597(16) .0604(15) .089(2) .0070(13) .0249(15) -.0065(14) C13 .0705(17) .0474(13) .087(2) .0110(12) .0161(15) -.0010(13) C14 .0778(19) .0514(14) .092(2) -.0023(13) .0283(17) .0108(14) C15 .0616(15) .0571(14) .0764(18) .0010(12) .0286(14) .0059(12) F1 .1079(16) .0534(10) .141(2) .0213(10) .0375(15) .0041(11) Cl1 .0562(4) .0926(5) .0674(4) .0033(3) .0241(3) .0171(3) O4 .0851(16) .0808(15) .121(2) .0081(12) .0527(15) .0094(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0727 .0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .3639 .7018 '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 C4 N1 C1 110.6(2) C4 N1 C5 108.1(2) C1 N1 C5 114.0(2) C4 N1 H1N 114(2) C1 N1 H1N 99(2) C5 N1 H1N 110.7(19) N1 C4 C3 110.3(3) N1 C4 H4A 109.4 C3 C4 H4A 109.4 N1 C4 H4B 109.3 C3 C4 H4B 109.0 H4A C4 H4B 109.5 O1 C3 C4 111.7(3) O1 C3 H3A 109.3 C4 C3 H3A 109.1 O1 C3 H3B 108.6 C4 C3 H3B 108.5 H3A C3 H3B 109.5 C3 O1 C2 109.4(2) O1 C2 C1 112.1(3) O1 C2 H2A 108.6 C1 C2 H2A 108.8 O1 C2 H2B 108.9 C1 C2 H2B 108.9 H2A C2 H2B 109.5 N1 C1 C2 109.0(2) N1 C1 H1A 109.6 C2 C1 H1A 109.5 N1 C1 H1B 109.7 C2 C1 H1B 109.6 H1A C1 H1B 109.5 N1 C5 C6 114.1(2) N1 C5 H5A 108.3 C6 C5 H5A 108.3 N1 C5 H5B 108.2 C6 C5 H5B 108.4 H5A C5 H5B 109.5 O2 C6 C5 111.3(2) O2 C6 C8 105.1(2) C5 C6 C8 110.4(2) O2 C6 H6 111.5 C5 C6 H6 106.3 C8 C6 H6 112.4 C7 O2 C6 109.63(19) O3 C7 N2 128.5(2) O3 C7 O2 122.4(2) N2 C7 O2 109.0(2) C7 N2 N3 120.0(2) C7 N2 C8 113.2(2) N3 N2 C8 125.65(19) N2 C8 C6 100.7(2) N2 C8 H8A 111.5 C6 C8 H8A 111.3 N2 C8 H8B 111.8 C6 C8 H8B 111.8 H8A C8 H8B 109.5 C9 N3 N2 115.8(2) N3 C9 C10 122.8(2) N3 C9 H9 119.5 C10 C9 H9 117.5 C15 C10 C11 118.9(2) C15 C10 C9 117.6(2) C11 C10 C9 123.5(2) C12 C11 C10 120.3(3) C12 C11 H11 119.9 C10 C11 H11 119.9 C13 C12 C11 118.8(3) C13 C12 H12 120.7 C11 C12 H12 120.5 F1 C13 C12 118.8(3) F1 C13 C14 118.2(3) C12 C13 C14 123.0(3) C13 C14 C15 117.5(3) C13 C14 H14 121.3 C15 C14 H14 121.1 C14 C15 C10 121.4(3) C14 C15 H15 114.3 C10 C15 H15 124.2 H41 O4 H42 116.5 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 N1 C4 . 1.480(4) ? N1 C1 . 1.487(3) ? N1 C5 . 1.497(3) ? N1 H1N . .84(3) ? C4 C3 . 1.495(4) ? C4 H4A . .9600 ? C4 H4B . .9600 ? C3 O1 . 1.406(4) ? C3 H3A . .9600 ? C3 H3B . .9600 ? O1 C2 . 1.410(4) ? C2 C1 . 1.515(4) ? C2 H2A . .9599 ? C2 H2B . .9600 ? C1 H1A . .9600 ? C1 H1B . .9600 ? C5 C6 . 1.497(4) ? C5 H5A . .9599 ? C5 H5B . .9600 ? C6 O2 . 1.453(3) ? C6 C8 . 1.526(3) ? C6 H6 . .9600 ? O2 C7 . 1.357(3) ? C7 O3 . 1.203(3) ? C7 N2 . 1.347(3) ? N2 N3 . 1.369(3) ? N2 C8 . 1.448(3) ? C8 H8A . .9601 ? C8 H8B . .9600 ? N3 C9 . 1.274(3) ? C9 C10 . 1.460(3) ? C9 H9 . .8338 ? C10 C15 . 1.382(4) ? C10 C11 . 1.385(4) ? C11 C12 . 1.377(4) ? C11 H11 . .9599 ? C12 C13 . 1.359(4) ? C12 H12 . .9600 ? C13 F1 . 1.358(3) ? C13 C14 . 1.368(5) ? C14 C15 . 1.379(4) ? C14 H14 . .9600 ? C15 H15 . .9234 ? O4 H41 . .8579 ? O4 H42 . .8485 ? 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 O4 H41 Cl1 3_667 .86 2.42 3.225(3) 156.9 O4 H42 O3 1_655 .85 2.11 2.914(3) 158.9 O4 H42 N3 1_655 .85 2.88 3.473(3) 128.4 N1 H1N Cl1 . .84(3) 2.23(3) 3.051(3) 165(3) C4 H4A O3 1_655 .96 2.45 3.390(4) 165.1 C5 H5A O4 . .96 2.29 3.243(4) 173.3 C5 H5B Cl1 1_556 .96 2.81 3.715(3) 157.9 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 C1 C2 O1 C3 -61.5(4) C2 O1 C3 C4 61.3(4) O1 C3 C4 N1 -57.8(4) C3 C4 N1 C1 53.2(3) C4 N1 C1 C2 -52.5(3) N1 C1 C2 O1 57.3(4) C6 O2 C7 N2 -5.3(3) O2 C7 N2 C8 -5.4(3) C7 N2 C8 C6 12.7(3) N2 C8 C6 O2 -14.7(3) C8 C6 O2 C7 13.0(3) N2 N3 C9 C10 179.5(2) C4 N1 C5 C6 171.6(2) N1 C5 C6 C8 -155.2(2) C1 N1 C5 C6 -64.9(3) N1 C5 C6 O2 88.5(3)