(2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl­amino]-3-hydroxy­butyric acid monohydrate

Ji, C.; Cui, Y.; Yang, D.; Guo, C.

doi:10.1107/S1600536808017832

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1292

doi:10.1107/S1600536808017832

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(2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]-3-hydroxybutyric acid monohydrate

Chun-xiang Ji,^a Yong-tao Cui,^a Dong-ling Yang ^b and Cheng Guo ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technolgy, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China, and ^bNanjing FroChem Tech Co. Ltd., Xinmofan Road No. 36 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: guocheng@njut.edu.cn

(Received 17 April 2008; accepted 12 June 2008; online 19 June 2008)

In the title compound, C₁₁H₁₇N₃O₆·H₂O, an important building block of the medicine cefbuperazone sodium, the piperazine ring adopts a screw-boat conformation. Intermolecular O—H⋯O and intramolecular N—H⋯O hydrogen bonds are observed. The water molecule participates as both donor and acceptor in this framework.

Related literature

For related literature, see: Anger et al. (2001 ); Özcan et al. (2003 ); Rondu et al. (1997 ); Saikawa et al. (1981 ).

Experimental

Crystal data

C₁₁H₁₇N₃O₆·H₂O
M_r = 305.29
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.4640 (19) Å
b = 11.389 (2) Å
c = 13.611 (3) Å
V = 1467.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.955, T_max = 0.977
1519 measured reflections
1519 independent reflections
1287 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: <1%

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.105
S = 1.04
1519 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2	0.86	1.99	2.647 (3)	132
O7—H7A⋯O2	0.85 (2)	1.98 (2)	2.817 (4)	169 (5)
O4—H4⋯O7ⁱ	0.75 (5)	1.85 (5)	2.593 (4)	170 (5)
O6—H6⋯O1ⁱⁱ	0.83 (4)	1.95 (4)	2.772 (3)	167 (4)
O7—H7B⋯O6ⁱⁱⁱ	0.815 (19)	2.07 (3)	2.803 (4)	149 (4)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017832/bh2173sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017832/bh2173Isup2.hkl

checkCIF report

Comment top

Some derivatives of piperazine are important chemical materials (Saikawa et al., 1981) with pharmaceutical properties (Rondu et al., 1997) for example against migraine, and are calcium channel antagonist (Anger et al., 2001). As part of our studies in this area, we report here the crystal structure of the title compound, (I).

The refined molecular structure of (I) is shown in Fig. 1. The title compound includes a piperzaine and a threonine moieties, and the asymmetric unit is completed by one lattice water molecule. The piperazine ring adopts a screw-boat conformation with atoms C4 and C6 displaced by 0.104 (8) and 0.596 (2) Å, respectively, from the mean plane through atoms N1, C3, N2 and C5. The dihedral angle between N1/C3/N2/C5 and N2/C7/N3/C8 planes is 4.1°.

The threonine molecular group has two chiral atoms, C8 and C10, and adopts a configuration in agreement with previous reports (e.g. Özcan et al., 2003). The separation O6···O1 suggests an interaction between the ketone and the carboxyl group (Table 1). The water molecule is linked to the main molecule via O—H···O hydrogen bonds. These hydrogen bonds are effective in the stabilization of the crystal structure.

Related literature top

For related literature, see: Anger et al. (2001); Özcan et al. (2003); Rondu et al. (1997); Saikawa et al. (1981).

Experimental top

To a suspension of 2.0 g of L-threonine [(2S,3R)-2-amino-3-hydroxybutanoic acid] in methylene chloride (50 ml), 6.6 ml of trimethylchlorosilane were added, after which 7.1 ml of triethylamine were added dropwise at 273 K. The mixture was heated to 293 K for 2 h, and then a mixture of 4-ethyl-2,3-dioxo-1-piperazinecarbonyl chloride and triethylamine was added to the reaction mixture. After stirring for 1 h, the solvent was removed under reduced pressure. To the residue, 30 ml of water was added, and the pH was adjusted to 8 with NaHCO₃, after which the solution was washed with 50 ml of ethyl acetate. Acetonitrile (50 ml) was added to the solution. The pH of the mixture was adjusted to 1 with HCl. The mixture was then saturated with NaCl, and the acetonitrile layer was thereafter separated. The aqueous layer was extracted with acetonitrile (3 × 50 ml), the combined acetonitrile layers were washed with saturated NaCl, and then distilled in vacuo to remove the solvent. The residue was recrystallized from ethanol to obtain 3.2 g of (I). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. ¹H NMR (DMSO): δ 3.78–4.30 (m, 4H), 3.28–3.75 (m, 4H), 1.13 (d, 3H), 1.11 (t, 3H).

Computing details top

Data collection: CAD–4 Software (Enraf–Nonius, 1989); cell refinement: CAD–4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 30% probability level. Dashed lines indicate O—H···O and N—H···O hydrogen bonds.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

(2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]-3-hydroxybutyric acid monohydrate top

Crystal data top

C₁₁H₁₇N₃O₆·H₂O	F(000) = 648
M_r = 305.29	D_x = 1.382 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.4640 (19) Å	θ = 10–13°
b = 11.389 (2) Å	µ = 0.12 mm⁻¹
c = 13.611 (3) Å	T = 293 K
V = 1467.1 (5) Å³	Block, colourless
Z = 4	0.40 × 0.30 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1287 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.1°, θ_min = 2.3°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
T_min = 0.955, T_max = 0.977	l = 0→16
1519 measured reflections	3 standard reflections every 200 reflections
1519 independent reflections	intensity decay: <1%

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0652P)² + 0.1558P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
1519 reflections	Δρ_max = 0.16 e Å⁻³
205 parameters	Δρ_min = −0.16 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (4)

Crystal data top

C₁₁H₁₇N₃O₆·H₂O	V = 1467.1 (5) Å³
M_r = 305.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.4640 (19) Å	µ = 0.12 mm⁻¹
b = 11.389 (2) Å	T = 293 K
c = 13.611 (3) Å	0.40 × 0.30 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1287 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.955, T_max = 0.977	3 standard reflections every 200 reflections
1519 measured reflections	intensity decay: <1%
1519 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	2 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.16 e Å⁻³
1519 reflections	Δρ_min = −0.16 e Å⁻³
205 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2982 (5)	0.8688 (4)	0.3149 (3)	0.0802 (14)
H1A	0.2231	0.9061	0.2793	0.120*
H1B	0.3779	0.9207	0.3183	0.120*
H1C	0.2666	0.8505	0.3802	0.120*
C2	0.3399 (4)	0.7585 (3)	0.2637 (3)	0.0517 (9)
H2A	0.2588	0.7066	0.2601	0.062*
H2B	0.3683	0.7771	0.1970	0.062*
C3	0.5900 (3)	0.7122 (3)	0.2851 (2)	0.0401 (7)
C4	0.7064 (3)	0.6501 (3)	0.3450 (2)	0.0385 (7)
C5	0.5156 (3)	0.5303 (3)	0.4161 (3)	0.0549 (10)
H5A	0.4893	0.4738	0.3659	0.066*
H5B	0.4997	0.4945	0.4798	0.066*
C6	0.4272 (3)	0.6364 (3)	0.4065 (3)	0.0544 (9)
H6B	0.3282	0.6145	0.4091	0.065*
H6C	0.4461	0.6891	0.4609	0.065*
C7	0.7632 (3)	0.4841 (3)	0.4570 (2)	0.0403 (7)
C8	1.0033 (3)	0.4380 (3)	0.5054 (2)	0.0373 (7)
H8A	0.9525	0.4006	0.5598	0.045*
C9	1.1128 (3)	0.5210 (3)	0.5489 (2)	0.0390 (7)
C10	1.0768 (3)	0.3423 (3)	0.4465 (2)	0.0425 (7)
H10A	1.1384	0.2984	0.4913	0.051*
C11	0.9774 (4)	0.2570 (3)	0.3990 (3)	0.0570 (9)
H11A	1.0306	0.1992	0.3633	0.085*
H11B	0.9161	0.2982	0.3547	0.085*
H11C	0.9219	0.2188	0.4487	0.085*
N1	0.4564 (2)	0.6970 (2)	0.31326 (19)	0.0416 (7)
N2	0.6683 (3)	0.5610 (2)	0.4054 (2)	0.0397 (6)
N3	0.9022 (2)	0.5055 (2)	0.44847 (19)	0.0383 (6)
H3A	0.9314	0.5594	0.4091	0.046*
O1	0.6257 (2)	0.7700 (3)	0.21398 (19)	0.0635 (8)
O2	0.8292 (2)	0.6821 (2)	0.33274 (19)	0.0534 (7)
O3	0.7145 (3)	0.4047 (2)	0.5047 (2)	0.0648 (8)
O4	1.1991 (3)	0.4638 (2)	0.6080 (2)	0.0654 (8)
H4	1.254 (6)	0.501 (4)	0.632 (3)	0.072 (15)*
O5	1.1208 (2)	0.6236 (2)	0.53094 (18)	0.0506 (6)
O6	1.1642 (3)	0.4009 (2)	0.3763 (2)	0.0600 (7)
H6	1.217 (5)	0.354 (4)	0.347 (3)	0.064 (12)*
O7	0.9118 (3)	0.9195 (3)	0.3221 (2)	0.0663 (8)
H7A	0.894 (5)	0.847 (2)	0.332 (3)	0.080*
H7B	0.909 (5)	0.937 (4)	0.2641 (17)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.071 (3)	0.088 (3)	0.081 (3)	0.038 (3)	−0.034 (3)	−0.023 (3)
C2	0.0347 (16)	0.063 (2)	0.057 (2)	0.0056 (17)	−0.0130 (16)	−0.0023 (18)
C3	0.0329 (15)	0.0434 (17)	0.0441 (17)	0.0010 (14)	0.0026 (14)	0.0032 (15)
C4	0.0277 (15)	0.0402 (16)	0.0476 (17)	−0.0004 (13)	0.0058 (14)	0.0067 (15)
C5	0.0280 (15)	0.056 (2)	0.081 (3)	−0.0076 (15)	0.0075 (17)	0.017 (2)
C6	0.0271 (15)	0.067 (2)	0.069 (2)	−0.0013 (16)	0.0102 (17)	0.016 (2)
C7	0.0325 (15)	0.0342 (15)	0.0541 (18)	−0.0024 (13)	0.0063 (15)	0.0054 (16)
C8	0.0310 (14)	0.0399 (15)	0.0410 (15)	−0.0004 (14)	−0.0004 (13)	0.0091 (15)
C9	0.0337 (15)	0.0446 (17)	0.0389 (16)	0.0053 (14)	0.0036 (14)	−0.0016 (14)
C10	0.0366 (15)	0.0394 (16)	0.0515 (17)	0.0076 (15)	−0.0094 (16)	−0.0010 (15)
C11	0.051 (2)	0.0486 (18)	0.071 (2)	0.0071 (17)	−0.016 (2)	−0.0059 (19)
N1	0.0261 (12)	0.0516 (16)	0.0471 (15)	0.0005 (11)	0.0009 (12)	0.0043 (13)
N2	0.0228 (11)	0.0387 (13)	0.0577 (15)	−0.0007 (11)	0.0055 (12)	0.0078 (13)
N3	0.0283 (12)	0.0399 (14)	0.0468 (14)	0.0006 (11)	0.0037 (12)	0.0092 (12)
O1	0.0382 (13)	0.0902 (19)	0.0622 (14)	0.0059 (13)	0.0057 (12)	0.0350 (15)
O2	0.0280 (11)	0.0555 (14)	0.0765 (16)	0.0003 (11)	0.0077 (12)	0.0252 (13)
O3	0.0400 (13)	0.0541 (15)	0.100 (2)	−0.0055 (12)	0.0030 (14)	0.0349 (15)
O4	0.0657 (18)	0.0583 (16)	0.0722 (18)	−0.0039 (15)	−0.0344 (16)	0.0042 (14)
O5	0.0444 (13)	0.0402 (12)	0.0672 (15)	−0.0013 (11)	0.0009 (12)	−0.0009 (12)
O6	0.0441 (13)	0.0687 (17)	0.0672 (16)	0.0033 (14)	0.0184 (13)	−0.0123 (14)
O7	0.0633 (16)	0.0645 (16)	0.0710 (16)	−0.0032 (15)	0.0206 (16)	−0.0012 (16)

Geometric parameters (Å, º) top

C1—C2	1.491 (5)	C7—N3	1.343 (4)
C1—H1A	0.9600	C7—N2	1.438 (4)
C1—H1B	0.9600	C8—N3	1.451 (4)
C1—H1C	0.9600	C8—C10	1.521 (4)
C2—N1	1.470 (4)	C8—C9	1.522 (4)
C2—H2A	0.9700	C8—H8A	0.9800
C2—H2B	0.9700	C9—O5	1.196 (4)
C3—O1	1.218 (4)	C9—O4	1.319 (4)
C3—N1	1.333 (4)	C10—O6	1.430 (4)
C3—C4	1.542 (4)	C10—C11	1.499 (5)
C4—O2	1.229 (3)	C10—H10A	0.9800
C4—N2	1.354 (4)	C11—H11A	0.9600
C5—C6	1.476 (5)	C11—H11B	0.9600
C5—N2	1.495 (4)	C11—H11C	0.9600
C5—H5A	0.9700	N3—H3A	0.8600
C5—H5B	0.9700	O4—H4	0.75 (5)
C6—N1	1.470 (4)	O6—H6	0.83 (4)
C6—H6B	0.9700	O7—H7A	0.85 (2)
C6—H6C	0.9700	O7—H7B	0.815 (19)
C7—O3	1.205 (4)

C2—C1—H1A	109.5	N3—C8—C10	113.6 (2)
C2—C1—H1B	109.5	N3—C8—C9	109.1 (2)
H1A—C1—H1B	109.5	C10—C8—C9	109.8 (2)
C2—C1—H1C	109.5	N3—C8—H8A	108.1
H1A—C1—H1C	109.5	C10—C8—H8A	108.1
H1B—C1—H1C	109.5	C9—C8—H8A	108.1
N1—C2—C1	112.7 (3)	O5—C9—O4	124.6 (3)
N1—C2—H2A	109.1	O5—C9—C8	124.8 (3)
C1—C2—H2A	109.1	O4—C9—C8	110.6 (3)
N1—C2—H2B	109.1	O6—C10—C11	112.2 (3)
C1—C2—H2B	109.1	O6—C10—C8	106.4 (3)
H2A—C2—H2B	107.8	C11—C10—C8	113.9 (3)
O1—C3—N1	124.2 (3)	O6—C10—H10A	108.1
O1—C3—C4	118.0 (3)	C11—C10—H10A	108.1
N1—C3—C4	117.8 (3)	C8—C10—H10A	108.1
O2—C4—N2	123.8 (3)	C10—C11—H11A	109.5
O2—C4—C3	117.8 (3)	C10—C11—H11B	109.5
N2—C4—C3	118.3 (2)	H11A—C11—H11B	109.5
C6—C5—N2	110.3 (3)	C10—C11—H11C	109.5
C6—C5—H5A	109.6	H11A—C11—H11C	109.5
N2—C5—H5A	109.6	H11B—C11—H11C	109.5
C6—C5—H5B	109.6	C3—N1—C2	121.2 (3)
N2—C5—H5B	109.6	C3—N1—C6	119.2 (3)
H5A—C5—H5B	108.1	C2—N1—C6	118.6 (2)
N1—C6—C5	110.7 (3)	C4—N2—C7	125.9 (2)
N1—C6—H6B	109.5	C4—N2—C5	119.5 (3)
C5—C6—H6B	109.5	C7—N2—C5	114.4 (2)
N1—C6—H6C	109.5	C7—N3—C8	120.2 (3)
C5—C6—H6C	109.5	C7—N3—H3A	119.9
H6B—C6—H6C	108.1	C8—N3—H3A	119.9
O3—C7—N3	123.9 (3)	C9—O4—H4	115 (4)
O3—C7—N2	118.8 (3)	C10—O6—H6	111 (3)
N3—C7—N2	117.3 (3)	H7A—O7—H7B	113 (5)

O1—C3—C4—O2	16.1 (5)	C1—C2—N1—C6	72.6 (4)
N1—C3—C4—O2	−165.3 (3)	C5—C6—N1—C3	−44.8 (4)
O1—C3—C4—N2	−161.7 (3)	C5—C6—N1—C2	146.7 (3)
N1—C3—C4—N2	16.9 (4)	O2—C4—N2—C7	−6.0 (5)
N2—C5—C6—N1	55.3 (4)	C3—C4—N2—C7	171.7 (3)
N3—C8—C9—O5	−6.4 (4)	O2—C4—N2—C5	179.1 (3)
C10—C8—C9—O5	118.6 (3)	C3—C4—N2—C5	−3.2 (4)
N3—C8—C9—O4	174.5 (3)	O3—C7—N2—C4	−176.4 (3)
C10—C8—C9—O4	−60.4 (3)	N3—C7—N2—C4	3.4 (5)
N3—C8—C10—O6	67.5 (3)	O3—C7—N2—C5	−1.3 (5)
C9—C8—C10—O6	−54.9 (3)	N3—C7—N2—C5	178.5 (3)
N3—C8—C10—C11	−56.5 (4)	C6—C5—N2—C4	−32.7 (5)
C9—C8—C10—C11	−179.0 (3)	C6—C5—N2—C7	151.8 (3)
O1—C3—N1—C2	−5.0 (5)	O3—C7—N3—C8	−5.7 (5)
C4—C3—N1—C2	176.5 (3)	N2—C7—N3—C8	174.5 (2)
O1—C3—N1—C6	−173.2 (3)	C10—C8—N3—C7	101.8 (3)
C4—C3—N1—C6	8.3 (4)	C9—C8—N3—C7	−135.4 (3)
C1—C2—N1—C3	−95.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2	0.86	1.99	2.647 (3)	132
O7—H7A···O2	0.85 (2)	1.98 (2)	2.817 (4)	169 (5)
O4—H4···O7ⁱ	0.75 (5)	1.85 (5)	2.593 (4)	170 (5)
O6—H6···O1ⁱⁱ	0.83 (4)	1.95 (4)	2.772 (3)	167 (4)
O7—H7B···O6ⁱⁱⁱ	0.82 (2)	2.07 (3)	2.803 (4)	149 (4)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇N₃O₆·H₂O
M_r	305.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.4640 (19), 11.389 (2), 13.611 (3)
V (Å³)	1467.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.955, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	1519, 1519, 1287
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.105, 1.04
No. of reflections	1519
No. of parameters	205
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: CAD–4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2	0.86	1.99	2.647 (3)	132.0
O7—H7A···O2	0.85 (2)	1.98 (2)	2.817 (4)	169 (5)
O4—H4···O7ⁱ	0.75 (5)	1.85 (5)	2.593 (4)	170 (5)
O6—H6···O1ⁱⁱ	0.83 (4)	1.95 (4)	2.772 (3)	167 (4)
O7—H7B···O6ⁱⁱⁱ	0.815 (19)	2.07 (3)	2.803 (4)	149 (4)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2.

References

Anger, T., Madge, D. J., Mulla, M. & Riddall, D. (2001). J. Med. Chem. 44, 115–137. Web of Science CrossRef PubMed CAS Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Özcan, Y., İde, S., Şakiyan, İ. & Logoglu, E. (2003). J. Mol. Struct. 658, 207–213. Google Scholar
Rondu, F., Le Bihan, G., Wang, X., Lamouri, A., Touboul, E., Dive, G., Bellahsene, T., Pfeiffer, B., Renard, P., Guardiola-Lemaitre, B. et al. (1997). J. Med. Chem. 40, 3793–3803. CrossRef CAS PubMed Web of Science Google Scholar
Saikawa, I., Takano, S., Imaizumi, H., Takakura, I., Ochiai, H., Yasuda, T., Taki, H., Tai, M. & Kodama, Y. (1981). US Patent No. 4 263 292. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 7| July 2008| Page o1292

doi:10.1107/S1600536808017832

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl­amino]-3-hy­droxy­butyric acid monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]-3-hydroxybutyric acid monohydrate