(2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl-amino]-3-hydroxy-butyric acid monohydrate.

In the title compound, C(11)H(17)N(3)O(6)·H(2)O, an important building block of the medicine cefbuperazone sodium, the piperazine ring adopts a screw-boat conformation. Inter-molecular O-H⋯O and intra-molecular N-H⋯O hydrogen bonds are observed. The water mol-ecule 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 = 305.29

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.105

S = 1.04

1519 reflections

205 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H17N3O6·H2O	F000 = 648
Mr = 305.29	Dx = 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 = 10–13º
b = 11.389 (2) Å	µ = 0.12 mm−1
c = 13.611 (3) Å	T = 293 (2) K
V = 1467.1 (5) Å3	Block, colourless
Z = 4	0.40 × 0.30 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.0000
Radiation source: fine-focus sealed tube	θmax = 25.1º
Monochromator: graphite	θmin = 2.3º
T = 293(2) K	h = 0→11
ω/2θ scans	k = 0→13
Absorption correction: ψ scan(North et al., 1968)	l = 0→16
Tmin = 0.955, Tmax = 0.977	3 standard reflections
1519 measured reflections	every 200 reflections
1519 independent reflections	intensity decay: <1%
1287 reflections with I > 2σ(I)

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(Fo2) + (0.0652P)2 + 0.1558P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1519 reflections	Δρmax = 0.16 e Å−3
205 parameters	Δρmin = −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)

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) ; (iii) .