Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006742/wn6015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006742/wn6015Isup2.hkl |
CCDC reference: 165674
All H atoms except these of the water molecule and that bonded to atom N1 were placed in calculated positions and were treated as riding on the adjacent C atom. They were refined with individual isotropic displacement parameters equal to 1.2 times the value of the equivalent displacement parameter of the parent C atom for aryl H atoms and equal to 1.5 times for other H atoms. The positional parameters and isotropic displacement parameter of the H atom bonded to atom N1 were free to refine.
Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia 1997); software used to prepare material for publication: SHELXL97.
C15H19FN3O3+·Cl−·H2O | Dx = 1.390 Mg m−3 |
Mr = 361.80 | Melting point: 501.2-502.1 K K |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54056 Å |
a = 8.9570 (9) Å | Cell parameters from 99 reflections |
b = 27.968 (3) Å | θ = 5–60° |
c = 7.137 (1) Å | µ = 2.28 mm−1 |
β = 104.820 (9)° | T = 291 K |
V = 1728.4 (4) Å3 | Plate, colourless |
Z = 4 | 0.39 × 0.35 × 0.17 mm |
F(000) = 760 |
Kuma KM-4 diffractometer | 2689 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 81.5°, θmin = 3.2° |
ω–2θ scans | h = −11→11 |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | k = 0→35 |
Tmin = 0.471, Tmax = 0.698 | l = 0→9 |
3674 measured reflections | 3 standard reflections every 100 reflections |
3674 independent reflections | intensity decay: 1.7% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.201 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.1136P)2 + 0.499P] where P = (Fo2 + 2Fc2)/3 |
3674 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.87 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C15H19FN3O3+·Cl−·H2O | V = 1728.4 (4) Å3 |
Mr = 361.80 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 8.9570 (9) Å | µ = 2.28 mm−1 |
b = 27.968 (3) Å | T = 291 K |
c = 7.137 (1) Å | 0.39 × 0.35 × 0.17 mm |
β = 104.820 (9)° |
Kuma KM-4 diffractometer | 2689 reflections with I > 2σ(I) |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | Rint = 0.000 |
Tmin = 0.471, Tmax = 0.698 | 3 standard reflections every 100 reflections |
3674 measured reflections | intensity decay: 1.7% |
3674 independent reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.201 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.87 e Å−3 |
3674 reflections | Δρmin = −0.42 e Å−3 |
221 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4961 (3) | 0.37889 (7) | 1.2497 (4) | 0.0536 (5) | |
C4 | 0.6564 (3) | 0.37213 (11) | 1.3677 (5) | 0.0672 (7) | |
H4A | 0.7196 | 0.3979 | 1.3434 | 0.101* | |
H4B | 0.6574 | 0.3718 | 1.5025 | 0.101* | |
C3 | 0.7197 (4) | 0.32576 (12) | 1.3176 (5) | 0.0752 (8) | |
H3A | 0.8228 | 0.3217 | 1.3973 | 0.113* | |
H3B | 0.7216 | 0.3267 | 1.1838 | 0.113* | |
O1 | 0.6284 (3) | 0.28678 (8) | 1.3449 (4) | 0.0831 (7) | |
C2 | 0.4785 (4) | 0.29185 (11) | 1.2224 (6) | 0.0820 (10) | |
H2A | 0.4857 | 0.2934 | 1.0906 | 0.123* | |
H2B | 0.4179 | 0.2646 | 1.2384 | 0.123* | |
C1 | 0.3994 (4) | 0.33671 (9) | 1.2671 (5) | 0.0654 (7) | |
H1A | 0.3871 | 0.3349 | 1.3967 | 0.098* | |
H1B | 0.2998 | 0.3397 | 1.1772 | 0.098* | |
C5 | 0.4372 (3) | 0.42510 (9) | 1.3088 (4) | 0.0597 (6) | |
H5A | 0.5114 | 0.4496 | 1.3052 | 0.090* | |
H5B | 0.4273 | 0.4216 | 1.4389 | 0.090* | |
C6 | 0.2843 (3) | 0.44029 (9) | 1.1820 (4) | 0.0559 (6) | |
H6 | 0.2817 | 0.4293 | 1.0538 | 0.084* | |
O2 | 0.1574 (2) | 0.42051 (6) | 1.2498 (3) | 0.0595 (5) | |
C7 | 0.0536 (3) | 0.45548 (9) | 1.2555 (4) | 0.0546 (6) | |
O3 | −0.0693 (2) | 0.44726 (7) | 1.2881 (3) | 0.0688 (6) | |
N2 | 0.1095 (2) | 0.49766 (7) | 1.2124 (3) | 0.0540 (5) | |
C8 | 0.2657 (3) | 0.49440 (9) | 1.1912 (4) | 0.0571 (6) | |
H8A | 0.2752 | 0.5095 | 1.0740 | 0.086* | |
H8B | 0.3393 | 0.5081 | 1.2999 | 0.086* | |
N3 | 0.0318 (2) | 0.53915 (7) | 1.2260 (3) | 0.0511 (5) | |
C9 | 0.1007 (3) | 0.57767 (8) | 1.2022 (4) | 0.0520 (5) | |
H9 | 0.1908 | 0.5764 | 1.1904 | 0.078* | |
C10 | 0.0335 (3) | 0.62494 (9) | 1.2104 (4) | 0.0509 (5) | |
C11 | −0.0999 (3) | 0.63272 (9) | 1.2703 (4) | 0.0580 (6) | |
H11 | −0.1512 | 0.6063 | 1.3128 | 0.070* | |
C12 | −0.1591 (4) | 0.67820 (10) | 1.2690 (5) | 0.0685 (8) | |
H12 | −0.2519 | 0.6837 | 1.3095 | 0.082* | |
C13 | −0.0838 (4) | 0.71510 (10) | 1.2095 (5) | 0.0690 (8) | |
C14 | 0.0503 (4) | 0.70938 (10) | 1.1538 (5) | 0.0727 (8) | |
H14 | 0.1018 | 0.7361 | 1.1138 | 0.087* | |
C15 | 0.1081 (3) | 0.66366 (9) | 1.1551 (5) | 0.0630 (7) | |
H15 | 0.2012 | 0.6618 | 1.1223 | 0.076* | |
F1 | −0.1430 (3) | 0.75989 (6) | 1.2068 (4) | 0.0998 (7) | |
Cl1 | 0.50494 (8) | 0.39291 (3) | 0.82881 (11) | 0.0705 (3) | |
O4 | 0.6843 (3) | 0.51101 (9) | 1.3309 (4) | 0.0908 (8) | |
H41 | 0.6610 | 0.5395 | 1.2889 | 0.136* | |
H42 | 0.7563 | 0.4973 | 1.2938 | 0.136* | |
H1N | 0.486 (3) | 0.3783 (10) | 1.129 (5) | 0.055 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0571 (12) | 0.0474 (10) | 0.0609 (13) | 0.0011 (8) | 0.0235 (10) | 0.0030 (9) |
C4 | 0.0591 (15) | 0.0639 (16) | 0.0797 (19) | −0.0027 (12) | 0.0199 (14) | −0.0039 (13) |
C3 | 0.0697 (18) | 0.0774 (19) | 0.080 (2) | 0.0126 (15) | 0.0226 (16) | 0.0052 (15) |
O1 | 0.0876 (16) | 0.0604 (12) | 0.0974 (17) | 0.0152 (11) | 0.0166 (13) | 0.0108 (11) |
C2 | 0.085 (2) | 0.0521 (15) | 0.107 (3) | 0.0010 (14) | 0.022 (2) | −0.0083 (16) |
C1 | 0.0662 (17) | 0.0505 (14) | 0.0836 (19) | −0.0060 (11) | 0.0268 (15) | 0.0026 (12) |
C5 | 0.0632 (15) | 0.0523 (13) | 0.0636 (15) | −0.0010 (11) | 0.0161 (12) | −0.0054 (11) |
C6 | 0.0587 (14) | 0.0528 (13) | 0.0597 (14) | −0.0012 (11) | 0.0215 (12) | −0.0016 (10) |
O2 | 0.0569 (10) | 0.0470 (9) | 0.0793 (12) | −0.0006 (7) | 0.0260 (9) | 0.0026 (8) |
C7 | 0.0532 (13) | 0.0506 (12) | 0.0615 (14) | −0.0009 (10) | 0.0174 (11) | −0.0029 (10) |
O3 | 0.0567 (11) | 0.0628 (11) | 0.0952 (15) | −0.0075 (9) | 0.0345 (11) | 0.0000 (10) |
N2 | 0.0495 (11) | 0.0471 (10) | 0.0691 (13) | 0.0014 (8) | 0.0220 (10) | 0.0013 (9) |
C8 | 0.0538 (14) | 0.0510 (13) | 0.0727 (16) | 0.0015 (10) | 0.0276 (12) | 0.0040 (11) |
N3 | 0.0517 (11) | 0.0467 (10) | 0.0560 (11) | 0.0021 (8) | 0.0158 (9) | −0.0026 (8) |
C9 | 0.0472 (12) | 0.0507 (12) | 0.0591 (14) | 0.0014 (9) | 0.0155 (10) | −0.0001 (10) |
C10 | 0.0505 (12) | 0.0502 (12) | 0.0513 (12) | 0.0006 (10) | 0.0121 (10) | −0.0016 (9) |
C11 | 0.0535 (14) | 0.0525 (13) | 0.0708 (16) | −0.0020 (10) | 0.0209 (12) | −0.0052 (11) |
C12 | 0.0597 (16) | 0.0604 (15) | 0.089 (2) | 0.0070 (13) | 0.0249 (15) | −0.0065 (14) |
C13 | 0.0705 (17) | 0.0474 (13) | 0.087 (2) | 0.0110 (12) | 0.0161 (15) | −0.0010 (13) |
C14 | 0.0778 (19) | 0.0514 (14) | 0.092 (2) | −0.0023 (13) | 0.0283 (17) | 0.0108 (14) |
C15 | 0.0616 (15) | 0.0571 (14) | 0.0764 (18) | 0.0010 (12) | 0.0286 (14) | 0.0059 (12) |
F1 | 0.1079 (16) | 0.0534 (10) | 0.141 (2) | 0.0213 (10) | 0.0375 (15) | 0.0041 (11) |
Cl1 | 0.0562 (4) | 0.0926 (5) | 0.0674 (4) | 0.0033 (3) | 0.0241 (3) | 0.0171 (3) |
O4 | 0.0851 (16) | 0.0808 (15) | 0.121 (2) | 0.0081 (12) | 0.0527 (15) | 0.0094 (14) |
N1—C4 | 1.480 (4) | C7—O3 | 1.203 (3) |
N1—C1 | 1.487 (3) | C7—N2 | 1.347 (3) |
N1—C5 | 1.497 (3) | N2—N3 | 1.369 (3) |
N1—H1N | 0.84 (3) | N2—C8 | 1.448 (3) |
C4—C3 | 1.495 (4) | C8—H8A | 0.9601 |
C4—H4A | 0.9600 | C8—H8B | 0.9600 |
C4—H4B | 0.9600 | N3—C9 | 1.274 (3) |
C3—O1 | 1.406 (4) | C9—C10 | 1.460 (3) |
C3—H3A | 0.9600 | C9—H9 | 0.8338 |
C3—H3B | 0.9600 | C10—C15 | 1.382 (4) |
O1—C2 | 1.410 (4) | C10—C11 | 1.385 (4) |
C2—C1 | 1.515 (4) | C11—C12 | 1.377 (4) |
C2—H2A | 0.9599 | C11—H11 | 0.9599 |
C2—H2B | 0.9600 | C12—C13 | 1.359 (4) |
C1—H1A | 0.9600 | C12—H12 | 0.9600 |
C1—H1B | 0.9600 | C13—F1 | 1.358 (3) |
C5—C6 | 1.497 (4) | C13—C14 | 1.368 (5) |
C5—H5A | 0.9599 | C14—C15 | 1.379 (4) |
C5—H5B | 0.9600 | C14—H14 | 0.9600 |
C6—O2 | 1.453 (3) | C15—H15 | 0.9234 |
C6—C8 | 1.526 (3) | O4—H41 | 0.8579 |
C6—H6 | 0.9600 | O4—H42 | 0.8485 |
O2—C7 | 1.357 (3) | ||
C4—N1—C1 | 110.6 (2) | O2—C6—H6 | 111.5 |
C4—N1—C5 | 108.1 (2) | C5—C6—H6 | 106.3 |
C1—N1—C5 | 114.0 (2) | C8—C6—H6 | 112.4 |
C4—N1—H1N | 114 (2) | C7—O2—C6 | 109.63 (19) |
C1—N1—H1N | 99 (2) | O3—C7—N2 | 128.5 (2) |
C5—N1—H1N | 110.7 (19) | O3—C7—O2 | 122.4 (2) |
N1—C4—C3 | 110.3 (3) | N2—C7—O2 | 109.0 (2) |
N1—C4—H4A | 109.4 | C7—N2—N3 | 120.0 (2) |
C3—C4—H4A | 109.4 | C7—N2—C8 | 113.2 (2) |
N1—C4—H4B | 109.3 | N3—N2—C8 | 125.65 (19) |
C3—C4—H4B | 109.0 | N2—C8—C6 | 100.7 (2) |
H4A—C4—H4B | 109.5 | N2—C8—H8A | 111.5 |
O1—C3—C4 | 111.7 (3) | C6—C8—H8A | 111.3 |
O1—C3—H3A | 109.3 | N2—C8—H8B | 111.8 |
C4—C3—H3A | 109.1 | C6—C8—H8B | 111.8 |
O1—C3—H3B | 108.6 | H8A—C8—H8B | 109.5 |
C4—C3—H3B | 108.5 | C9—N3—N2 | 115.8 (2) |
H3A—C3—H3B | 109.5 | N3—C9—C10 | 122.8 (2) |
C3—O1—C2 | 109.4 (2) | N3—C9—H9 | 119.5 |
O1—C2—C1 | 112.1 (3) | C10—C9—H9 | 117.5 |
O1—C2—H2A | 108.6 | C15—C10—C11 | 118.9 (2) |
C1—C2—H2A | 108.8 | C15—C10—C9 | 117.6 (2) |
O1—C2—H2B | 108.9 | C11—C10—C9 | 123.5 (2) |
C1—C2—H2B | 108.9 | C12—C11—C10 | 120.3 (3) |
H2A—C2—H2B | 109.5 | C12—C11—H11 | 119.9 |
N1—C1—C2 | 109.0 (2) | C10—C11—H11 | 119.9 |
N1—C1—H1A | 109.6 | C13—C12—C11 | 118.8 (3) |
C2—C1—H1A | 109.5 | C13—C12—H12 | 120.7 |
N1—C1—H1B | 109.7 | C11—C12—H12 | 120.5 |
C2—C1—H1B | 109.6 | F1—C13—C12 | 118.8 (3) |
H1A—C1—H1B | 109.5 | F1—C13—C14 | 118.2 (3) |
N1—C5—C6 | 114.1 (2) | C12—C13—C14 | 123.0 (3) |
N1—C5—H5A | 108.3 | C13—C14—C15 | 117.5 (3) |
C6—C5—H5A | 108.3 | C13—C14—H14 | 121.3 |
N1—C5—H5B | 108.2 | C15—C14—H14 | 121.1 |
C6—C5—H5B | 108.4 | C14—C15—C10 | 121.4 (3) |
H5A—C5—H5B | 109.5 | C14—C15—H15 | 114.3 |
O2—C6—C5 | 111.3 (2) | C10—C15—H15 | 124.2 |
O2—C6—C8 | 105.1 (2) | H41—O4—H42 | 116.5 |
C5—C6—C8 | 110.4 (2) | ||
C1—C2—O1—C3 | −61.5 (4) | C7—N2—C8—C6 | 12.7 (3) |
C2—O1—C3—C4 | 61.3 (4) | N2—C8—C6—O2 | −14.7 (3) |
O1—C3—C4—N1 | −57.8 (4) | C8—C6—O2—C7 | 13.0 (3) |
C3—C4—N1—C1 | 53.2 (3) | N2—N3—C9—C10 | 179.5 (2) |
C4—N1—C1—C2 | −52.5 (3) | C4—N1—C5—C6 | 171.6 (2) |
N1—C1—C2—O1 | 57.3 (4) | N1—C5—C6—C8 | −155.2 (2) |
C6—O2—C7—N2 | −5.3 (3) | C1—N1—C5—C6 | −64.9 (3) |
O2—C7—N2—C8 | −5.4 (3) | N1—C5—C6—O2 | 88.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H41···Cl1i | 0.86 | 2.42 | 3.225 (3) | 157 |
O4—H42···O3ii | 0.85 | 2.11 | 2.914 (3) | 159 |
O4—H42···N3ii | 0.85 | 2.88 | 3.473 (3) | 128 |
N1—H1N···Cl1 | 0.84 (3) | 2.23 (3) | 3.051 (3) | 165 (3) |
C4—H4A···O3ii | 0.96 | 2.45 | 3.390 (4) | 165 |
C5—H5A···O4 | 0.96 | 2.29 | 3.243 (4) | 173 |
C5—H5B···Cl1iii | 0.96 | 2.81 | 3.715 (3) | 158 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y, z; (iii) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H19FN3O3+·Cl−·H2O |
Mr | 361.80 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 8.9570 (9), 27.968 (3), 7.137 (1) |
β (°) | 104.820 (9) |
V (Å3) | 1728.4 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.28 |
Crystal size (mm) | 0.39 × 0.35 × 0.17 |
Data collection | |
Diffractometer | Kuma KM-4 diffractometer |
Absorption correction | Numerical (X-RED; Stoe & Cie, 1999) |
Tmin, Tmax | 0.471, 0.698 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3674, 3674, 2689 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.642 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.201, 1.12 |
No. of reflections | 3674 |
No. of parameters | 221 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.87, −0.42 |
Computer programs: KM-4 Software (Kuma, 1993), KM-4 Software, DATAPROC (Kuma 1998), SHELXS97 (Sheldrick, 1990a), SHELXL97 (Sheldrick, 1997), XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H41···Cl1i | 0.86 | 2.42 | 3.225 (3) | 156.9 |
O4—H42···O3ii | 0.85 | 2.11 | 2.914 (3) | 158.9 |
O4—H42···N3ii | 0.85 | 2.88 | 3.473 (3) | 128.4 |
N1—H1N···Cl1 | 0.84 (3) | 2.23 (3) | 3.051 (3) | 165 (3) |
C4—H4A···O3ii | 0.96 | 2.45 | 3.390 (4) | 165.1 |
C5—H5A···O4 | 0.96 | 2.29 | 3.243 (4) | 173.3 |
C5—H5B···Cl1iii | 0.96 | 2.81 | 3.715 (3) | 157.9 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y, z; (iii) x, y, z+1. |
In the Pharmaceutical Research Institute in Warsaw, a series of derivatives of 3-amino-2-oxazolidinone have been prepared (Chilmonczyk et al., 1997). It has been found that the oxazolidinone derivative 5-morpholinomethyl-3-(4-chlorobenzylidenamino)-2-oxazolidinone, (I) hereafter, is a potential psychotropic drug (Chilmonczyk, 1995). Preliminary clinical data show that the compound exhibits antidepressive activity in humans (Rybakowski & Araszkiewicz, 1999). It can be supposed that other derivatives of this class can also exhibit biological activity. It is generally accepted that the specific, energetically preferred conformation of a compound (so-called bioactive conformation) determines the nature of interactions with its molecular target, the pharmacological receptor. Therefore, it is of fundamental importance to get an insight into such molecular parameters as charge distribution, most preferred conformation or distances between specified points within a molecule (Krzywda et al., 2000). Bartczak et al. (2001) have determined the structure of the chloride monohydrate of (I) and found that the primary location of molecular interaction with an acid residue within a putative receptor site is at the morpholine N atom. The structure of 5-morpholinomethyl-3-(4-fluorobenzylidenamino)-2-oxazolidinone, (II), has also been previously determined (Kruszynski et al., 2001) but the primary location of molecular interaction with an acid residue within a putative receptor site was only supposed on the basis of similar molecular geometry of (II) and the chloride monohydrate of (I).
The perspective view of the title compound, (III), together with the atom-numbering scheme, is shown in Fig. 1. A l l interatomic distances are normal. The molecular geometry of (III) is similar to the chloride monohydrate of (I) (Bartczak et al., 2001) and (II). The weighted r.m.s. deviation for all atoms in (III) and inverted molecule (II) is 0.238 (3) Å; for (III) and (II), it is 0.229 (2) Å. The superposition of the two molecules (III) and (II) is shown in Fig. 2. The molecule of (III) shows signs of disorder, as was noticed in (II), but invoking this model did not improve the quality of structure; therefore the model was not applied.
In (III), a proton transfer takes place from hydrochloric acid to the atom N1. This confirms the presumption (Kruszynski et al., 2001) that the molecule interacts with an acid residue within a putative receptor through the atom N1. The oxazolidinone ring of (III) exists in the same almost ideal half-chair conformation as in (I); this can be detected by the asymmetry parameters (Duax & Norton, 1975). Values and positions of the asymmetry parameters for the oxazolidinone ring are shown in Fig. 3. According to the asymmetry parameters the morpholine ring exists in a slightly distorted chair conformation.
The structure of (III) is built up from strong and weak intermolecular hydrogen bonds to form the two dimensional infinite hydrogen-bond network (Fig. 4 and Table 2). The absence of an intermolecular hydrogen bond linking atoms C1 and O2 in (III) as in (II), which creates a fused three-membered ring system in the chloride monohydrate of (I) (Bartczak et al., 2001), might be one of the reasons for the signs of disorder observed in the molecule.