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The single-crystal X-ray diffraction study of the title compound,
N-[3-methyl-1-(4-methyl-2,5-dioxoimidazolidin-4-yl)buty]]acetamide monohydrate, C
11H
19N
3O
3·H
2O, confirms that the imidazolidinedione ring is in a planar conformation, as evidenced by NMR studies. There are chains of intermolecular hydrogen bonds involving the imido carbonyl-O atom and the acetamido carbonyl-O atom as acceptors, and the water molecule as donor. The crystal packing is also stabilized by N—H
O intermolecular interactions.
Supporting information
CCDC reference: 162838
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.057
- wR factor = 0.166
- Data-to-parameter ratio = 20.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
PLAT_030 Alert B Refined Extinction parameter within range .... 1.50 Sigma
Alert Level C:
SHFSU_01 Alert C The absolute value of parameter shift to su ratio > 0.05
Absolute value of the parameter shift to su ratio given 0.065
Additional refinement cycles may be required.
WEIGH_01 Alert C Extra text has been found in the
_refine_ls_weighting_scheme field. This should be in the
_refine_ls_weighting_details field.
Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] wher
Weighting scheme identified as calc
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
2 Alert Level C = Please check
Potassium cyanide (1.3 g, 0.02 mol) and ammonium carbonate (6.283 g, 0.04 mol)
were dissolved in aqueous ethanol (200 ml) and 3-acetamido-5
methyl-hexan-2-one (1.7 g, 0.01 mol) was added. The clear reaction mixture was
heated at 333–343 K for 9 h and the solvent was removed by distillation. The
solid obtained was extracted with ethyl acetate. Evaporation of the ethyl
acetate gave a colourless solid which was recrystallized from 0.1 N
hydrochloric acid. Crystallization: 750 mg of title compound was dissolved in
7.0 ml me thanol and 3.0 ml (3 N HCl) and the solution was refluxed on a water
bath for 1 h and filtered using Whatmann filter paper. The hot solution was
allowed to cool to room temprature while methanol was allowed to evaporate.
When the volume of the solution was about 5.0 ml, 3–5 drops of conentrated
HCl was added along the sides of the container. Needle-like crystals were seen
after 16 h. The supernatant was transfered to another beaker and the crystals
were dried on a bed of tissue paper.
All H atoms, except for the water H atoms were included at calculated positions
and refined using a riding model. The water H atoms were found from difference
Fourier syntheses and were refined isotropically.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELX97 and PARST (Nardelli, 1983, 1995).
5-(1-Acetamido-3-methyl)butyl-5methyl-2,4-imidazolidinedione
top
Crystal data top
C11H19N3O3·H2O | F(000) = 560 |
Mr = 259.31 | Dx = 1.191 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2770 (1) Å | θ = 1.5–28.3° |
b = 19.7080 (4) Å | µ = 0.09 mm−1 |
c = 11.9399 (1) Å | T = 293 K |
β = 101.64° | Block, white |
V = 1446.67 (4) Å3 | 0.40 × 0.30 × 0.26 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2418 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.063 |
Graphite monochromator | θmax = 28.2°, θmin = 3.3° |
ω scans | h = −8→8 |
10168 measured reflections | k = −26→26 |
3536 independent reflections | l = −15→9 |
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)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.166 | Calculated w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max = 0.065 |
3536 reflections | Δρmax = 0.34 e Å−3 |
176 parameters | Δρmin = −0.36 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: 0.006 (4) |
Crystal data top
C11H19N3O3·H2O | V = 1446.67 (4) Å3 |
Mr = 259.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.2770 (1) Å | µ = 0.09 mm−1 |
b = 19.7080 (4) Å | T = 293 K |
c = 11.9399 (1) Å | 0.40 × 0.30 × 0.26 mm |
β = 101.64° | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2418 reflections with I > 2σ(I) |
10168 measured reflections | Rint = 0.063 |
3536 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.166 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | Δρmax = 0.34 e Å−3 |
3536 reflections | Δρmin = −0.36 e Å−3 |
176 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 | |
O1 | 0.31466 (19) | 0.44818 (6) | 0.39815 (12) | 0.0448 (3) | |
O2 | 0.8988 (2) | 0.41823 (7) | 0.43487 (12) | 0.0431 (3) | |
O3 | 0.7688 (2) | 0.60247 (7) | 0.28229 (13) | 0.0560 (4) | |
O4 | 0.2050 (2) | 0.78488 (6) | 0.14294 (15) | 0.0617 (5) | |
N1 | 0.2575 (2) | 0.55935 (6) | 0.33608 (12) | 0.0339 (3) | |
H1 | 0.1214 | 0.5631 | 0.3372 | 0.041* | |
N2 | 0.5788 (2) | 0.51240 (6) | 0.33750 (12) | 0.0334 (3) | |
H2 | 0.6771 | 0.4816 | 0.3420 | 0.040* | |
N3 | 0.0959 (2) | 0.68137 (7) | 0.18933 (13) | 0.0384 (4) | |
H3 | −0.0113 | 0.6583 | 0.2043 | 0.046* | |
C1 | −0.1523 (3) | 0.77553 (11) | 0.1853 (2) | 0.0645 (6) | |
H1A | −0.1361 | 0.7976 | 0.2582 | 0.097* | |
H1B | −0.2535 | 0.7387 | 0.1817 | 0.097* | |
H1C | −0.2058 | 0.8075 | 0.1256 | 0.097* | |
C2 | 0.0655 (3) | 0.74846 (8) | 0.17051 (16) | 0.0398 (4) | |
C3 | 0.2967 (2) | 0.64486 (8) | 0.18620 (14) | 0.0333 (4) | |
H3A | 0.4023 | 0.6775 | 0.1678 | 0.040* | |
C4 | 0.6048 (2) | 0.57753 (8) | 0.30615 (14) | 0.0336 (4) | |
C5 | 0.3908 (2) | 0.61488 (7) | 0.30639 (14) | 0.0312 (4) | |
C6 | 0.4305 (3) | 0.66987 (9) | 0.39918 (17) | 0.0491 (5) | |
H6A | 0.2941 | 0.6897 | 0.4063 | 0.074* | |
H6B | 0.5233 | 0.7044 | 0.3785 | 0.074* | |
H6C | 0.4990 | 0.6500 | 0.4708 | 0.074* | |
C7 | 0.3733 (2) | 0.50147 (7) | 0.36149 (14) | 0.0305 (3) | |
C8 | 0.2566 (3) | 0.59094 (9) | 0.09159 (16) | 0.0457 (5) | |
H8A | 0.3730 | 0.5578 | 0.1074 | 0.055* | |
H8B | 0.1218 | 0.5676 | 0.0943 | 0.055* | |
C9 | 0.2432 (4) | 0.61855 (10) | −0.02962 (17) | 0.0566 (5) | |
H9 | 0.1578 | 0.6605 | −0.0373 | 0.068* | |
C10 | 0.1258 (5) | 0.56736 (15) | −0.1183 (2) | 0.0895 (9) | |
H10A | 0.2043 | 0.5252 | −0.1102 | 0.134* | |
H10B | 0.1189 | 0.5850 | −0.1939 | 0.134* | |
H10C | −0.0189 | 0.5599 | −0.1061 | 0.134* | |
C11 | 0.4666 (6) | 0.63487 (17) | −0.0520 (3) | 0.1010 (10) | |
H11A | 0.5341 | 0.6689 | 0.0010 | 0.152* | |
H11B | 0.4530 | 0.6515 | −0.1287 | 0.152* | |
H11C | 0.5544 | 0.5946 | −0.0425 | 0.152* | |
H1O | 0.871 (4) | 0.3784 (13) | 0.414 (2) | 0.069 (7)* | |
H2O | 1.033 (5) | 0.4268 (13) | 0.420 (2) | 0.078 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0390 (6) | 0.0307 (6) | 0.0666 (9) | −0.0022 (5) | 0.0153 (6) | 0.0142 (5) |
O2 | 0.0370 (6) | 0.0307 (7) | 0.0653 (9) | 0.0031 (5) | 0.0191 (6) | −0.0002 (6) |
O3 | 0.0342 (6) | 0.0503 (8) | 0.0876 (11) | −0.0054 (6) | 0.0220 (7) | 0.0188 (7) |
O4 | 0.0527 (8) | 0.0317 (7) | 0.1072 (13) | 0.0011 (6) | 0.0320 (8) | 0.0211 (7) |
N1 | 0.0252 (6) | 0.0302 (7) | 0.0490 (9) | 0.0038 (5) | 0.0140 (6) | 0.0114 (6) |
N2 | 0.0266 (6) | 0.0283 (7) | 0.0476 (8) | 0.0044 (5) | 0.0131 (6) | 0.0055 (5) |
N3 | 0.0303 (7) | 0.0291 (7) | 0.0562 (9) | −0.0021 (5) | 0.0096 (6) | 0.0121 (6) |
C1 | 0.0430 (10) | 0.0446 (11) | 0.1070 (19) | 0.0095 (9) | 0.0176 (11) | 0.0152 (11) |
C2 | 0.0369 (8) | 0.0298 (8) | 0.0513 (11) | 0.0010 (7) | 0.0058 (7) | 0.0081 (7) |
C3 | 0.0334 (7) | 0.0245 (7) | 0.0430 (10) | −0.0010 (6) | 0.0104 (7) | 0.0067 (6) |
C4 | 0.0275 (7) | 0.0343 (8) | 0.0404 (9) | −0.0023 (6) | 0.0103 (6) | 0.0051 (6) |
C5 | 0.0310 (7) | 0.0253 (7) | 0.0391 (9) | 0.0004 (6) | 0.0112 (6) | 0.0046 (6) |
C6 | 0.0651 (12) | 0.0370 (9) | 0.0437 (11) | 0.0015 (8) | 0.0076 (9) | −0.0024 (7) |
C7 | 0.0266 (7) | 0.0294 (8) | 0.0361 (8) | −0.0012 (6) | 0.0081 (6) | 0.0029 (6) |
C8 | 0.0606 (11) | 0.0323 (9) | 0.0430 (11) | −0.0018 (8) | 0.0073 (9) | 0.0034 (7) |
C9 | 0.0823 (15) | 0.0451 (11) | 0.0413 (11) | 0.0069 (10) | 0.0096 (10) | 0.0049 (8) |
C10 | 0.126 (3) | 0.0854 (19) | 0.0504 (15) | −0.0083 (18) | 0.0027 (15) | −0.0112 (12) |
C11 | 0.134 (3) | 0.101 (2) | 0.080 (2) | −0.026 (2) | 0.0509 (19) | 0.0090 (16) |
Geometric parameters (Å, º) top
O1—C7 | 1.222 (2) | C3—C8 | 1.534 (2) |
O2—H1O | 0.83 (3) | C3—H3A | 0.9800 |
O2—H2O | 0.91 (3) | C4—C5 | 1.533 (2) |
O3—C4 | 1.225 (2) | C5—C6 | 1.534 (2) |
O4—C2 | 1.227 (2) | C6—H6A | 0.9600 |
N1—C7 | 1.354 (2) | C6—H6B | 0.9600 |
N1—C5 | 1.464 (2) | C6—H6C | 0.9600 |
N1—H1 | 0.8600 | C8—C9 | 1.532 (3) |
N2—C4 | 1.356 (2) | C8—H8A | 0.9700 |
N2—C7 | 1.393 (2) | C8—H8B | 0.9700 |
N2—H2 | 0.8600 | C9—C11 | 1.514 (4) |
N3—C2 | 1.348 (2) | C9—C10 | 1.538 (3) |
N3—C3 | 1.458 (2) | C9—H9 | 0.9800 |
N3—H3 | 0.8600 | C10—H10A | 0.9600 |
C1—C2 | 1.511 (3) | C10—H10B | 0.9600 |
C1—H1A | 0.9600 | C10—H10C | 0.9600 |
C1—H1B | 0.9600 | C11—H11A | 0.9600 |
C1—H1C | 0.9600 | C11—H11B | 0.9600 |
C3—C5 | 1.554 (2) | C11—H11C | 0.9600 |
| | | |
H1O—O2—H2O | 105 (2) | C5—C6—H6A | 109.5 |
C7—N1—C5 | 112.1 (1) | C5—C6—H6B | 109.5 |
C7—N1—H1 | 123.9 | H6A—C6—H6B | 109.5 |
C5—N1—H1 | 123.9 | C5—C6—H6C | 109.5 |
C4—N2—C7 | 111.8 (1) | H6A—C6—H6C | 109.5 |
C4—N2—H2 | 124.1 | H6B—C6—H6C | 109.5 |
C7—N2—H2 | 124.1 | O1—C7—N1 | 128.1 (1) |
C2—N3—C3 | 125.0 (1) | O1—C7—N2 | 124.4 (1) |
C2—N3—H3 | 117.5 | N1—C7—N2 | 107.5 (1) |
C3—N3—H3 | 117.5 | C9—C8—C3 | 114.77 (14) |
C2—C1—H1A | 109.5 | C9—C8—H8A | 108.6 |
C2—C1—H1B | 109.5 | C3—C8—H8A | 108.6 |
H1A—C1—H1B | 109.5 | C9—C8—H8B | 108.6 |
C2—C1—H1C | 109.5 | C3—C8—H8B | 108.6 |
H1A—C1—H1C | 109.5 | H8A—C8—H8B | 107.6 |
H1B—C1—H1C | 109.5 | C8—C9—C11 | 111.4 (2) |
O4—C2—N3 | 122.2 (2) | C8—C9—C10 | 110.15 (19) |
O4—C2—C1 | 122.4 (2) | C11—C9—C10 | 110.5 (2) |
N3—C2—C1 | 115.3 (2) | C8—C9—H9 | 108.2 |
N3—C3—C5 | 109.5 (2) | C11—C9—H9 | 108.2 |
N3—C3—C8 | 110.3 (2) | C10—C9—H9 | 108.2 |
C5—C3—C8 | 113.07 (13) | C9—C10—H10A | 109.5 |
N3—C3—H3A | 108.0 | C9—C10—H10B | 109.5 |
C5—C3—H3A | 108.0 | H10A—C10—H10B | 109.5 |
C8—C3—H3A | 108.0 | C9—C10—H10C | 109.5 |
O3—C4—N2 | 126.7 (2) | H10A—C10—H10C | 109.5 |
O3—C4—C5 | 125.9 (2) | H10B—C10—H10C | 109.5 |
N2—C4—C5 | 107.4 (1) | C9—C11—H11A | 109.5 |
N1—C5—C4 | 100.7 (1) | C9—C11—H11B | 109.5 |
N1—C5—C3 | 112.2 (1) | H11A—C11—H11B | 109.5 |
C4—C5—C3 | 110.5 (1) | C9—C11—H11C | 109.5 |
N1—C5—C6 | 111.8 (1) | H11A—C11—H11C | 109.5 |
C4—C5—C6 | 109.0 (1) | H11B—C11—H11C | 109.5 |
C3—C5—C6 | 111.9 (1) | | |
| | | |
C3—N3—C2—O4 | 3.7 (3) | N3—C3—C5—N1 | 69.7 (2) |
C3—N3—C2—C1 | −176.5 (2) | C8—C3—C5—N1 | −53.66 (18) |
C2—N3—C3—C5 | 117.0 (2) | N3—C3—C5—C4 | −178.75 (12) |
C2—N3—C3—C8 | −118.03 (18) | C8—C3—C5—C4 | 57.89 (18) |
C7—N2—C4—O3 | 178.4 (2) | N3—C3—C5—C6 | −56.97 (17) |
C7—N2—C4—C5 | −1.31 (18) | C8—C3—C5—C6 | 179.67 (15) |
C7—N1—C5—C4 | 5.8 (2) | C5—N1—C7—O1 | 173.56 (16) |
C7—N1—C5—C3 | 123.4 (1) | C5—N1—C7—N2 | −6.9 (2) |
C7—N1—C5—C6 | −109.85 (16) | C4—N2—C7—O1 | −175.4 (2) |
O3—C4—C5—N1 | 177.7 (2) | C4—N2—C7—N1 | 5.03 (19) |
N2—C4—C5—N1 | −2.6 (2) | N3—C3—C8—C9 | 77.9 (2) |
O3—C4—C5—C3 | 58.9 (2) | C5—C3—C8—C9 | −159.23 (16) |
N2—C4—C5—C3 | −121.37 (14) | C3—C8—C9—C11 | 77.0 (2) |
O3—C4—C5—C6 | −64.6 (2) | C3—C8—C9—C10 | −160.0 (2) |
N2—C4—C5—C6 | 115.11 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2 | 0.86 | 2.03 | 2.809 (2) | 151 |
N1—H1···O3i | 0.86 | 2.31 | 3.122 (2) | 157 |
N3—H3···O3i | 0.86 | 2.12 | 2.964 (2) | 166 |
O2—H1O···O4ii | 0.83 (3) | 1.99 (3) | 2.820 (2) | 177 (3) |
O2—H2O···O1iii | 0.91 (3) | 1.89 (3) | 2.796 (2) | 176 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | C11H19N3O3·H2O |
Mr | 259.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 6.2770 (1), 19.7080 (4), 11.9399 (1) |
β (°) | 101.64 |
V (Å3) | 1446.67 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.30 × 0.26 |
|
Data collection |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10168, 3536, 2418 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.664 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.166, 0.94 |
No. of reflections | 3536 |
No. of parameters | 176 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.36 |
Selected geometric parameters (Å, º) topO1—C7 | 1.222 (2) | N2—C4 | 1.356 (2) |
O3—C4 | 1.225 (2) | N2—C7 | 1.393 (2) |
O4—C2 | 1.227 (2) | N3—C2 | 1.348 (2) |
N1—C7 | 1.354 (2) | N3—C3 | 1.458 (2) |
N1—C5 | 1.464 (2) | C4—C5 | 1.533 (2) |
| | | |
C7—N1—C5 | 112.1 (1) | O3—C4—N2 | 126.7 (2) |
C4—N2—C7 | 111.8 (1) | O3—C4—C5 | 125.9 (2) |
C2—N3—C3 | 125.0 (1) | N2—C4—C5 | 107.4 (1) |
O4—C2—N3 | 122.2 (2) | N1—C5—C4 | 100.7 (1) |
O4—C2—C1 | 122.4 (2) | N1—C5—C3 | 112.2 (1) |
N3—C2—C1 | 115.3 (2) | O1—C7—N1 | 128.1 (1) |
N3—C3—C5 | 109.5 (2) | O1—C7—N2 | 124.4 (1) |
N3—C3—C8 | 110.3 (2) | N1—C7—N2 | 107.5 (1) |
| | | |
C3—N3—C2—O4 | 3.7 (3) | N3—C3—C5—N1 | 69.7 (2) |
C3—N3—C2—C1 | −176.5 (2) | C5—N1—C7—N2 | −6.9 (2) |
C7—N2—C4—O3 | 178.4 (2) | C4—N2—C7—O1 | −175.4 (2) |
O3—C4—C5—N1 | 177.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2 | 0.86 | 2.03 | 2.809 (2) | 151 |
N1—H1···O3i | 0.86 | 2.31 | 3.122 (2) | 157 |
N3—H3···O3i | 0.86 | 2.12 | 2.964 (2) | 166 |
O2—H1O···O4ii | 0.83 (3) | 1.99 (3) | 2.820 (2) | 177 (3) |
O2—H2O···O1iii | 0.91 (3) | 1.89 (3) | 2.796 (2) | 176 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x+1, y, z. |
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Hydantoins, well known for their central nervous system activity (Tunnicliff, 1996; Morkunas & Miller, 1997), have been reported to possess a variety of pharmacological properties. 5,5-Disubstituted hydantoins often exhibit narcotic and hypnotic activity and have been used for the treatment of chorea and epilepsy. Amino hydantoins are used in the treatment of urinary tract infections, as muscle relaxants and as bactericides. The structure consists of a 2,4-imidazolidinedione ring (commonly known as hydantoin) with a methyl group substituted at the 5 position. A number of 2,4-imidazolidinedione derivatives have been shown to act as inhibitors of metalloproteins (Kelly et al., 1997) and exihibit anti-inflamatory and antifungal activities (Malhotra et al., 1990). Recently 5,5-disubstituted hydantoins have been reported to possess potent inhibitory activity towards HIV protease (Comber, 1992, 1997) and act as sodium channel blockers (Lang et al., 1997; Wayne et al., 1994). Also, hydantoins are attractive substrates for the synthesis of amino acids (Edward & Robert, 1994). In a continuation of our endeavour to design small antimicrobial peptidomimetics, the title compound, (I), was synthesized as an intermediate for an α,β-diamino acid. The structure was determined as a part of the characterization process. Of the two possible diastereomers, only one appears to have been selectively crystallized in our method. Preferential crystallization of hydantoin isomers has been reported in the literature (Ndzie et al., 1997).
Fig. 1 shows the ZORTEP plot (Zsolnai, 1997) of (I) along with the atom-numbering scheme. The whole molecule is not essentially planar, but the five-membered ring is essentially planar. The NMR spectrum of the title compound in DMSO-d6 shows two singlets at 10.67 and 7.62 p.p.m. corresponding to the imide and amide NH protons, respectively. This observation suggests a planar ring conformation, in agreement with a quasi-planar conformation proposed based on the existence of four-bond couplings between amide and imide protons in 1,3-positions of the imidazolidindione ring (Erzsebet et al., 1998). The dihedral angle between the least-squares plane through atoms C3/C8/C9/C10/C11 and the imidazolidine ring is 81.9 (1)°. The dihedral angle between the least-squares planes through atoms C3/C8/C9/C10/C11 and C3/N3/C2/O4/C1 is 77.3 (1)°. The dihedral angle between the least-squares planes through atoms C3/N3/C2/O4/C1 and the five-membered ring is 4.59 (1)°. In the imidazolidine ring, the values of the N1—C5 and C4—C5 distances, and the N1—C5—C4 angle (see Table 1) are in agreement with the literature data (Camerman & Camerman, 1971; Florencio et al., 1978; Verdier et al., 1977, 1979; Fujiwara et al., 1979; Koch et al., 1975), the observed values for the above are in the ranges 1.45–1.48, 1.51–1.55 Å and 99–101°, respectively. The torsion angle C5—C3—C8—C9 of -159.2 (2)° describes the conformation of the portion of the side chain as (-)antiperiplanar about C3—C8.
The packing is stabilized by O—H···O and N—H···O intermolecular hydrogen bonds·The solvent molecule plays a major role in the packing of the molecule. Packing shows that each molecule is bound to the neighbours through hydrogen bonds to form chains running parallel to one another in the crystal, as in the β form (Evans, 1979).