A series of derivatives of 3-amino-2-oxazolidinone have been prepared. The 5-morpholinomethyl-3-(4-chlorobenzylideneamino)-2-oxazolidinone derivative is a potential psychotropic drug. Preliminary clinical data showed that the compound exhibits antidepressive activity in humans. The molecular geometry of the title compound, C
15H
18FN
3O
3, is similar to 5-morpholinomethyl-3-(4-chlorobenzylideneamino)-2-oxazolidinone. Two atoms of the title compound are disordered so that two different conformations of the oxazolidinone ring were found; one is a twist and the other is an envelope conformation. The crystal structure of title compound is formed by weak intermolecular C—H
O hydrogen bonds resulting in a two-dimensional infinite hydrogen-bond network.
Supporting information
CCDC reference: 165640
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.075
- wR factor = 0.177
- Data-to-parameter ratio = 12.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_301 Alert C Main Residue Disorder ........................ 8.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound was prepared according to the method of Chilmonczyk et
al. (1997).
Data collection: CrysAlis CCD (UNIL IC & Kuma, 2000); cell refinement: CrysAlis RED (UNIL IC & Kuma, 2000); data reduction: CrysAlis RED; 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) ORTEP-3 (Farrugia 1997); software used to prepare material for publication: SHELXL97.
4-{3-[(4-Fluorobenzylidene)amino]-2-oxo-1,3-oxazolidin-5-ylmethyl}morpholine
top
Crystal data top
C15H18FN3O3 | F(000) = 324 |
Mr = 307.32 | Dx = 1.371 Mg m−3 |
Triclinic, P1 | Melting point: 432.6-433.5 K K |
a = 6.4808 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.9636 (9) Å | Cell parameters from 1319 reflections |
c = 12.2753 (11) Å | θ = 5–22° |
α = 91.600 (9)° | µ = 0.11 mm−1 |
β = 101.048 (10)° | T = 291 K |
γ = 106.114 (12)° | Plate, colourless |
V = 744.62 (12) Å3 | 0.30 × 0.11 × 0.08 mm |
Z = 2 | |
Data collection top
Kuma KM4-CCD diffractometer | 2638 independent reflections |
Radiation source: fine-focus sealed tube | 2090 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
ω scans | θmax = 25.1°, θmin = 3.4° |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | h = −7→7 |
Tmin = 0.969, Tmax = 0.992 | k = −11→11 |
2638 measured reflections | l = 0→14 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.075 | H-atom parameters constrained |
wR(F2) = 0.177 | w = 1/[σ2(Fo2) + (0.0691P)2 + 0.2292P] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max < 0.001 |
2638 reflections | Δρmax = 0.20 e Å−3 |
219 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.020 (5) |
Crystal data top
C15H18FN3O3 | γ = 106.114 (12)° |
Mr = 307.32 | V = 744.62 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.4808 (7) Å | Mo Kα radiation |
b = 9.9636 (9) Å | µ = 0.11 mm−1 |
c = 12.2753 (11) Å | T = 291 K |
α = 91.600 (9)° | 0.30 × 0.11 × 0.08 mm |
β = 101.048 (10)° | |
Data collection top
Kuma KM4-CCD diffractometer | 2638 independent reflections |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | 2090 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.992 | Rint = 0.000 |
2638 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.075 | 0 restraints |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.20 | Δρmax = 0.20 e Å−3 |
2638 reflections | Δρmin = −0.17 e Å−3 |
219 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | −0.1389 (5) | 0.2692 (3) | 0.8864 (3) | 0.0623 (8) | |
H1A | −0.0254 | 0.3475 | 0.9298 | 0.075* | |
H1B | −0.0816 | 0.2375 | 0.8263 | 0.075* | |
C2 | −0.2009 (6) | 0.1533 (4) | 0.9585 (3) | 0.0730 (10) | |
H2A | −0.3082 | 0.0735 | 0.9136 | 0.088* | |
H2B | −0.0722 | 0.1244 | 0.9895 | 0.088* | |
O1 | −0.2894 (5) | 0.1940 (3) | 1.04620 (19) | 0.0946 (9) | |
C3 | −0.4751 (6) | 0.2383 (5) | 1.0036 (3) | 0.0888 (12) | |
H3A | −0.5300 | 0.2694 | 1.0649 | 0.107* | |
H3B | −0.5898 | 0.1597 | 0.9613 | 0.107* | |
C4 | −0.4230 (6) | 0.3549 (4) | 0.9303 (3) | 0.0799 (11) | |
H4A | −0.5557 | 0.3792 | 0.8991 | 0.096* | |
H4B | −0.3193 | 0.4370 | 0.9741 | 0.096* | |
N1 | −0.3302 (4) | 0.3137 (3) | 0.8410 (2) | 0.0657 (8) | |
C5A | −0.2649 (9) | 0.4568 (6) | 0.7954 (5) | 0.0528 (19) | 0.571 (9) |
H5A1 | −0.3910 | 0.4928 | 0.7786 | 0.063* | 0.571 (9) |
H5A2 | −0.1519 | 0.5225 | 0.8505 | 0.063* | 0.571 (9) |
C6A | −0.1805 (9) | 0.4409 (8) | 0.6916 (6) | 0.0491 (16) | 0.571 (9) |
H6A | −0.2449 | 0.3476 | 0.6515 | 0.059* | 0.571 (9) |
C5B | −0.3304 (10) | 0.3687 (8) | 0.7263 (6) | 0.045 (2) | 0.429 (9) |
H5B1 | −0.2970 | 0.3029 | 0.6775 | 0.054* | 0.429 (9) |
H5B2 | −0.4752 | 0.3763 | 0.6944 | 0.054* | 0.429 (9) |
C6B | −0.1636 (12) | 0.5100 (11) | 0.7339 (7) | 0.046 (2) | 0.429 (9) |
H6B | −0.1574 | 0.5756 | 0.7962 | 0.055* | 0.429 (9) |
C8 | −0.2067 (4) | 0.5637 (4) | 0.6167 (3) | 0.0633 (9) | |
H8A | −0.3040 | 0.5281 | 0.5452 | 0.076* | |
H8B | −0.2615 | 0.6300 | 0.6535 | 0.076* | |
N2 | 0.0155 (4) | 0.6262 (3) | 0.6047 (2) | 0.0643 (8) | |
C7 | 0.1620 (4) | 0.5715 (3) | 0.6681 (3) | 0.0596 (8) | |
O2 | 0.0568 (3) | 0.4768 (2) | 0.72964 (19) | 0.0747 (7) | |
O3 | 0.3540 (3) | 0.5969 (3) | 0.6704 (2) | 0.0831 (8) | |
N3 | 0.0861 (4) | 0.7241 (2) | 0.53426 (19) | 0.0532 (6) | |
C9 | −0.0568 (4) | 0.7691 (3) | 0.4718 (2) | 0.0491 (7) | |
H9 | −0.2045 | 0.7331 | 0.4739 | 0.059* | |
C10 | 0.0094 (4) | 0.8765 (3) | 0.3973 (2) | 0.0445 (6) | |
C11 | 0.2295 (4) | 0.9442 (3) | 0.4010 (2) | 0.0531 (7) | |
H11 | 0.3366 | 0.9191 | 0.4512 | 0.064* | |
C12 | 0.2925 (5) | 1.0474 (3) | 0.3320 (2) | 0.0591 (8) | |
H12 | 0.4401 | 1.0926 | 0.3351 | 0.071* | |
C13 | 0.1316 (5) | 1.0815 (3) | 0.2588 (2) | 0.0589 (8) | |
C14 | −0.0859 (5) | 1.0196 (3) | 0.2522 (2) | 0.0593 (8) | |
H14 | −0.1910 | 1.0461 | 0.2017 | 0.071* | |
C15 | −0.1475 (5) | 0.9160 (3) | 0.3225 (2) | 0.0548 (7) | |
H15 | −0.2956 | 0.8726 | 0.3194 | 0.066* | |
F1 | 0.1919 (3) | 1.1824 (2) | 0.18925 (16) | 0.0858 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0587 (18) | 0.0667 (19) | 0.071 (2) | 0.0278 (15) | 0.0198 (15) | 0.0281 (16) |
C2 | 0.096 (2) | 0.079 (2) | 0.061 (2) | 0.0444 (19) | 0.0280 (18) | 0.0310 (18) |
O1 | 0.112 (2) | 0.139 (2) | 0.0575 (14) | 0.0628 (18) | 0.0329 (14) | 0.0357 (15) |
C3 | 0.093 (3) | 0.120 (3) | 0.073 (2) | 0.042 (2) | 0.045 (2) | 0.028 (2) |
C4 | 0.065 (2) | 0.071 (2) | 0.118 (3) | 0.0304 (18) | 0.036 (2) | 0.016 (2) |
N1 | 0.0506 (14) | 0.0818 (18) | 0.0805 (18) | 0.0293 (13) | 0.0302 (13) | 0.0502 (15) |
C5A | 0.054 (3) | 0.058 (4) | 0.054 (4) | 0.023 (3) | 0.017 (3) | 0.018 (3) |
C6A | 0.040 (3) | 0.057 (4) | 0.056 (4) | 0.020 (3) | 0.015 (3) | 0.015 (3) |
C5B | 0.034 (3) | 0.048 (4) | 0.050 (4) | 0.005 (3) | 0.009 (3) | 0.019 (4) |
C6B | 0.039 (4) | 0.057 (6) | 0.049 (5) | 0.016 (4) | 0.023 (3) | 0.018 (4) |
C8 | 0.0394 (15) | 0.093 (2) | 0.0670 (19) | 0.0227 (15) | 0.0223 (13) | 0.0443 (17) |
N2 | 0.0390 (12) | 0.0868 (18) | 0.0774 (17) | 0.0229 (12) | 0.0237 (12) | 0.0490 (15) |
C7 | 0.0424 (16) | 0.070 (2) | 0.074 (2) | 0.0199 (14) | 0.0203 (14) | 0.0348 (16) |
O2 | 0.0434 (11) | 0.0971 (17) | 0.0905 (16) | 0.0219 (11) | 0.0206 (11) | 0.0588 (14) |
O3 | 0.0381 (11) | 0.1048 (18) | 0.118 (2) | 0.0279 (11) | 0.0257 (12) | 0.0564 (16) |
N3 | 0.0481 (13) | 0.0596 (14) | 0.0585 (14) | 0.0158 (11) | 0.0231 (11) | 0.0270 (12) |
C9 | 0.0430 (14) | 0.0587 (17) | 0.0496 (15) | 0.0152 (12) | 0.0167 (12) | 0.0150 (13) |
C10 | 0.0484 (14) | 0.0470 (15) | 0.0390 (14) | 0.0126 (12) | 0.0125 (11) | 0.0090 (12) |
C11 | 0.0499 (16) | 0.0579 (17) | 0.0482 (16) | 0.0103 (13) | 0.0089 (12) | 0.0128 (13) |
C12 | 0.0543 (17) | 0.0582 (18) | 0.0594 (18) | 0.0041 (14) | 0.0151 (14) | 0.0151 (15) |
C13 | 0.076 (2) | 0.0518 (17) | 0.0488 (16) | 0.0112 (15) | 0.0219 (15) | 0.0180 (14) |
C14 | 0.0657 (18) | 0.0637 (19) | 0.0520 (17) | 0.0229 (15) | 0.0119 (14) | 0.0211 (15) |
C15 | 0.0496 (16) | 0.0610 (18) | 0.0560 (17) | 0.0171 (13) | 0.0130 (13) | 0.0157 (14) |
F1 | 0.1029 (15) | 0.0773 (13) | 0.0717 (12) | 0.0103 (11) | 0.0236 (11) | 0.0387 (11) |
Geometric parameters (Å, º) top
C1—N1 | 1.448 (3) | C6B—C8 | 1.551 (8) |
C1—C2 | 1.488 (4) | C6B—O2 | 1.563 (8) |
C1—H1A | 0.9700 | C6B—H6B | 0.9800 |
C1—H1B | 0.9700 | C8—N2 | 1.440 (3) |
C2—O1 | 1.412 (4) | C8—H8A | 0.9700 |
C2—H2A | 0.9700 | C8—H8B | 0.9700 |
C2—H2B | 0.9700 | N2—C7 | 1.353 (3) |
O1—C3 | 1.409 (4) | N2—N3 | 1.363 (3) |
C3—C4 | 1.493 (5) | C7—O3 | 1.193 (3) |
C3—H3A | 0.9700 | C7—O2 | 1.344 (3) |
C3—H3B | 0.9700 | N3—C9 | 1.275 (3) |
C4—N1 | 1.448 (4) | C9—C10 | 1.455 (3) |
C4—H4A | 0.9700 | C9—H9 | 0.9300 |
C4—H4B | 0.9700 | C10—C15 | 1.384 (4) |
N1—C5B | 1.525 (6) | C10—C11 | 1.390 (4) |
N1—C5A | 1.525 (6) | C11—C12 | 1.374 (4) |
C5A—C6A | 1.501 (10) | C11—H11 | 0.9300 |
C5A—H5A1 | 0.9700 | C12—C13 | 1.366 (4) |
C5A—H5A2 | 0.9700 | C12—H12 | 0.9300 |
C6A—O2 | 1.457 (6) | C13—C14 | 1.358 (4) |
C6A—C8 | 1.578 (6) | C13—F1 | 1.360 (3) |
C6A—H6A | 0.9800 | C14—C15 | 1.387 (4) |
C5B—C6B | 1.506 (13) | C14—H14 | 0.9300 |
C5B—H5B1 | 0.9700 | C15—H15 | 0.9300 |
C5B—H5B2 | 0.9700 | | |
| | | |
N1—C1—C2 | 109.4 (2) | H5B1—C5B—H5B2 | 108.0 |
N1—C1—H1A | 109.8 | C5B—C6B—C8 | 105.5 (7) |
C2—C1—H1A | 109.8 | C5B—C6B—O2 | 104.8 (7) |
N1—C1—H1B | 109.8 | C8—C6B—O2 | 98.6 (4) |
C2—C1—H1B | 109.8 | C5B—C6B—H6B | 115.3 |
H1A—C1—H1B | 108.2 | C8—C6B—H6B | 115.3 |
O1—C2—C1 | 111.8 (3) | O2—C6B—H6B | 115.3 |
O1—C2—H2A | 109.3 | N2—C8—C6B | 100.2 (3) |
C1—C2—H2A | 109.3 | N2—C8—C6A | 101.8 (3) |
O1—C2—H2B | 109.3 | C6B—C8—C6A | 30.3 (3) |
C1—C2—H2B | 109.3 | N2—C8—H8A | 111.4 |
H2A—C2—H2B | 107.9 | C6B—C8—H8A | 136.6 |
C3—O1—C2 | 110.5 (3) | C6A—C8—H8A | 111.4 |
O1—C3—C4 | 111.7 (3) | N2—C8—H8B | 111.4 |
O1—C3—H3A | 109.3 | C6B—C8—H8B | 84.4 |
C4—C3—H3A | 109.3 | C6A—C8—H8B | 111.4 |
O1—C3—H3B | 109.3 | H8A—C8—H8B | 109.3 |
C4—C3—H3B | 109.3 | C7—N2—N3 | 119.3 (2) |
H3A—C3—H3B | 107.9 | C7—N2—C8 | 113.1 (2) |
N1—C4—C3 | 110.5 (3) | N3—N2—C8 | 127.5 (2) |
N1—C4—H4A | 109.6 | O3—C7—O2 | 122.9 (3) |
C3—C4—H4A | 109.6 | O3—C7—N2 | 127.9 (3) |
N1—C4—H4B | 109.6 | O2—C7—N2 | 109.2 (2) |
C3—C4—H4B | 109.6 | C7—O2—C6A | 111.5 (3) |
H4A—C4—H4B | 108.1 | C7—O2—C6B | 106.5 (3) |
C1—N1—C4 | 110.1 (3) | C6A—O2—C6B | 31.2 (3) |
C1—N1—C5B | 114.3 (3) | C9—N3—N2 | 118.0 (2) |
C4—N1—C5B | 129.0 (4) | N3—C9—C10 | 120.5 (2) |
C1—N1—C5A | 111.2 (3) | N3—C9—H9 | 119.8 |
C4—N1—C5A | 97.3 (3) | C10—C9—H9 | 119.8 |
C5B—N1—C5A | 43.6 (3) | C15—C10—C11 | 118.4 (2) |
C6A—C5A—N1 | 108.6 (5) | C15—C10—C9 | 120.2 (2) |
C6A—C5A—H5A1 | 110.0 | C11—C10—C9 | 121.3 (2) |
N1—C5A—H5A1 | 110.0 | C12—C11—C10 | 121.5 (3) |
C6A—C5A—H5A2 | 110.0 | C12—C11—H11 | 119.3 |
N1—C5A—H5A2 | 110.0 | C10—C11—H11 | 119.3 |
H5A1—C5A—H5A2 | 108.3 | C13—C12—C11 | 117.9 (3) |
O2—C6A—C5A | 104.4 (6) | C13—C12—H12 | 121.1 |
O2—C6A—C8 | 102.0 (4) | C11—C12—H12 | 121.1 |
C5A—C6A—C8 | 109.4 (5) | C14—C13—F1 | 118.4 (3) |
O2—C6A—H6A | 113.4 | C14—C13—C12 | 123.2 (3) |
C5A—C6A—H6A | 113.4 | F1—C13—C12 | 118.4 (3) |
C8—C6A—H6A | 113.4 | C13—C14—C15 | 118.4 (3) |
C6B—C5B—N1 | 111.0 (6) | C13—C14—H14 | 120.8 |
C6B—C5B—H5B1 | 109.4 | C15—C14—H14 | 120.8 |
N1—C5B—H5B1 | 109.4 | C10—C15—C14 | 120.7 (3) |
C6B—C5B—H5B2 | 109.4 | C10—C15—H15 | 119.7 |
N1—C5B—H5B2 | 109.4 | C14—C15—H15 | 119.7 |
| | | |
O2—C7—N2—C8 | −2.9 (4) | N1—C5A—C6A—C8 | 156.2 (4) |
C7—N2—C8—C6A | −6.8 (5) | C1—N1—C5B—C6B | −71.8 (7) |
N2—C8—C6A—O2 | 12.9 (5) | N1—C5B—C6B—O2 | 85.4 (7) |
C8—C6A—O2—C7 | −15.9 (6) | N1—C5B—C6B—C8 | −171.1 (4) |
C6A—O2—C7—N2 | 12.6 (5) | C1—C2—O1—C3 | 58.1 (4) |
C7—N2—C8—C6B | 24.1 (6) | C2—O1—C3—C4 | −56.6 (4) |
N2—C8—C6B—O2 | −32.0 (6) | O1—C3—C4—N1 | 56.1 (4) |
C8—C6B—O2—C7 | 32.9 (6) | C3—C4—N1—C1 | −55.9 (4) |
C6B—O2—C7—N2 | −20.1 (5) | C4—N1—C1—C2 | 56.7 (4) |
C1—N1—C5A—C6A | 70.5 (5) | N1—C1—C2—O1 | −58.3 (4) |
N1—C5A—C6A—O2 | −95.2 (6) | N2—N3—C9—C10 | 178.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5A1···O3i | 0.97 | 2.40 | 3.314 (5) | 157 |
C8—H8B···O3i | 0.97 | 2.47 | 3.143 (3) | 126 |
C14—H14···O1ii | 0.93 | 2.54 | 3.375 (4) | 150 |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z−1. |
Experimental details
Crystal data |
Chemical formula | C15H18FN3O3 |
Mr | 307.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 6.4808 (7), 9.9636 (9), 12.2753 (11) |
α, β, γ (°) | 91.600 (9), 101.048 (10), 106.114 (12) |
V (Å3) | 744.62 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.30 × 0.11 × 0.08 |
|
Data collection |
Diffractometer | Kuma KM4-CCD diffractometer |
Absorption correction | Numerical (X-RED; Stoe & Cie, 1999) |
Tmin, Tmax | 0.969, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2638, 2638, 2090 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.596 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.075, 0.177, 1.20 |
No. of reflections | 2638 |
No. of parameters | 219 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.17 |
Selected torsion angles (º) topO2—C7—N2—C8 | −2.9 (4) | N1—C5A—C6A—C8 | 156.2 (4) |
C7—N2—C8—C6A | −6.8 (5) | C1—N1—C5B—C6B | −71.8 (7) |
N2—C8—C6A—O2 | 12.9 (5) | N1—C5B—C6B—O2 | 85.4 (7) |
C8—C6A—O2—C7 | −15.9 (6) | N1—C5B—C6B—C8 | −171.1 (4) |
C6A—O2—C7—N2 | 12.6 (5) | C1—C2—O1—C3 | 58.1 (4) |
C7—N2—C8—C6B | 24.1 (6) | C2—O1—C3—C4 | −56.6 (4) |
N2—C8—C6B—O2 | −32.0 (6) | O1—C3—C4—N1 | 56.1 (4) |
C8—C6B—O2—C7 | 32.9 (6) | C3—C4—N1—C1 | −55.9 (4) |
C6B—O2—C7—N2 | −20.1 (5) | C4—N1—C1—C2 | 56.7 (4) |
C1—N1—C5A—C6A | 70.5 (5) | N1—C1—C2—O1 | −58.3 (4) |
N1—C5A—C6A—O2 | −95.2 (6) | N2—N3—C9—C10 | 178.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5A1···O3i | 0.97 | 2.40 | 3.314 (5) | 157.0 |
C8—H8B···O3i | 0.97 | 2.47 | 3.143 (3) | 126.2 |
C14—H14···O1ii | 0.93 | 2.54 | 3.375 (4) | 150.2 |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, 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-chlorobenzylideneamino)-2-oxazolidinone, (II), 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 a specific,energetically preferred conformation of a compound (so-called bioactive conformation) decides about the nature of interactions with its molecular target or pharmacological receptor. Therefore, it is of basic importance to get an insight into such molecular parameters as charge distribution, the most preferred conformation or distances between specified points within a molecule (Krzywda et al., 2000).
A perspective view of the title compound, (I), together with the atom-numbering scheme are shown in Fig. 1. A l l interatomic distances are normal. The molecular geometry of (I) is similar to the chloride monohydrate of (II) (Bartczak et al., 2001). The weighted r.m.s. deviation for all atoms of (I) and the inverted molecule of (II) is 0.218 (2) Å. A fit of (I) and (II) is depicted in Fig. 2. Bartczak et al. (2001) found that the primary place of molecular interaction with an acid residue within a putative receptor site is on N1. Thus, we can suppose that for (I) proton transfer also occurs from the acid residue, and (I) will be interacting by the same N1 atom. The oxazolidinone ring exists in a twist and an envelope conformation shown by the asymmetry parameters; ΔC2 = 2.77 (5) and ΔCs = 4.62 (5), and ΔC2 = 13.66 (8) and ΔCs = 2.90 (6), respectively (Duax & Norton, 1975). According to asymmetry parameters, the morpholine ring exists in an almost ideal chair conformation. The structure of (I) is assembled by intermolecular weak C—H···O hydrogen bonds into a two-dimensional infinite hydrogen bond network (Fig. 3 and Table 2). The absence of an intermolecular hydrogen bond linking C1 and O2 in (I), which creates a fused three-membered ring system in (II), could be one of the reasons for the disorder observed in (I).
The decreased number of hydrogen bonds and its weakening in (I) does not change the molecular geometry, what suggests that inserting hydrochloric acid into the structure, even if it increases the number of hydrogen bonds, does not change its geometry and can eliminate disorder.