(S)-2-Ammonio-3-(4-nitro-phen-yl)propanoate monohydrate.

The title compound, C(9)H(10)N(2)O(4)·H(2)O, exists as a zwitterion with a deprotonated carboxyl group and a protonated amino group. The crystal packing is stabilized by N-H⋯O and O-H⋯O hydrogen bonds, building sheets parallel to the (001) plane. The absolute configuration was deduced from the synthetic pathway.

Related literature

For details of α-amino acids as precursors for the synthesis of novel biologically active compounds, see: Lucchese et al. (2007 ▶); Arki et al. (2004 ▶); Hauck et al. (2006 ▶); Azim et al. (2006 ▶).

Experimental

Crystal data

C9H10N2O4·H2O

M = 228.21

Orthorhombic,

a = 5.3141 (8) Å

b = 6.2823 (7) Å

c = 30.752 (4) Å

V = 1026.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 (2) K

0.25 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.970, T max = 0.974

10728 measured reflections

1466 independent reflections

1261 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.09

1466 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808011203/dn2340sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011203/dn2340Isup2.hkl

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

C9H10N2O4·H2O	F000 = 480
Mr = 228.21	Dx = 1.476 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1470 reflections
a = 5.3141 (8) Å	θ = 3.0–27.5º
b = 6.2823 (7) Å	µ = 0.12 mm−1
c = 30.752 (4) Å	T = 293 (2) K
V = 1026.7 (2) Å3	Block, colourless
Z = 4	0.25 × 0.20 × 0.20 mm

Rigaku Mercury2 diffractometer	1466 independent reflections
Radiation source: fine-focus sealed tube	1261 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.046
Detector resolution: 13.6612 pixels mm-1	θmax = 27.8º
T = 293(2) K	θmin = 3.3º
ω scans	h = −6→6
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −8→8
Tmin = 0.970, Tmax = 0.974	l = −40→40
10728 measured reflections

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.0774P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1466 reflections	Δρmax = 0.25 e Å−3
146 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O3	0.8183 (3)	0.4808 (3)	0.17549 (6)	0.0391 (4)
N2	0.2254 (4)	0.2416 (3)	0.20604 (6)	0.0346 (5)
H2A	0.2535	0.2749	0.2337	0.052*
H2B	0.1637	0.1101	0.2044	0.052*
H2C	0.1152	0.3328	0.1947	0.052*
O4	0.5036 (4)	0.5887 (3)	0.21776 (6)	0.0452 (5)
O1	1.3141 (4)	−0.0801 (4)	0.00871 (7)	0.0588 (6)
C1	1.0030 (5)	−0.0711 (4)	0.06148 (7)	0.0342 (6)
N1	1.2123 (5)	−0.1761 (4)	0.03883 (7)	0.0410 (5)
C7	0.4109 (5)	0.2328 (4)	0.13231 (8)	0.0369 (6)
H7A	0.2588	0.1496	0.1284	0.044*
H7B	0.3801	0.3735	0.1205	0.044*
C9	0.6059 (5)	0.4594 (4)	0.19280 (7)	0.0301 (5)
C8	0.4651 (4)	0.2532 (4)	0.18137 (7)	0.0283 (5)
H8	0.5704	0.1325	0.1901	0.034*
C3	0.6976 (6)	−0.0771 (4)	0.11762 (8)	0.0391 (6)
H3	0.6180	−0.1481	0.1403	0.047*
C5	0.7376 (5)	0.2308 (4)	0.07239 (8)	0.0376 (6)
H5	0.6850	0.3663	0.0643	0.045*
C4	0.6219 (5)	0.1297 (4)	0.10701 (7)	0.0327 (5)
C2	0.8872 (5)	−0.1774 (4)	0.09522 (8)	0.0405 (6)
H2	0.9366	−0.3146	0.1027	0.049*
C6	0.9322 (5)	0.1322 (4)	0.04943 (8)	0.0397 (6)
H6	1.0122	0.2016	0.0266	0.048*
O2	1.2768 (5)	−0.3521 (4)	0.05090 (7)	0.0589 (6)
O1W	0.0704 (4)	−0.1769 (3)	0.21144 (6)	0.0468 (5)
H1WB	0.0482	−0.2262	0.1860	0.070*
H1WC	0.1824	−0.2497	0.2244	0.070*

	U11	U22	U33	U12	U13	U23
O3	0.0300 (9)	0.0402 (10)	0.0470 (10)	−0.0064 (8)	0.0032 (7)	0.0024 (8)
N2	0.0329 (10)	0.0331 (10)	0.0377 (11)	−0.0040 (10)	0.0050 (8)	−0.0008 (9)
O4	0.0382 (10)	0.0407 (10)	0.0568 (11)	−0.0015 (9)	−0.0003 (9)	−0.0179 (9)
O1	0.0581 (13)	0.0682 (14)	0.0501 (12)	0.0028 (12)	0.0185 (10)	−0.0021 (11)
C1	0.0371 (14)	0.0365 (12)	0.0291 (11)	−0.0012 (11)	−0.0015 (10)	−0.0080 (10)
N1	0.0388 (12)	0.0467 (13)	0.0374 (11)	0.0022 (11)	−0.0027 (9)	−0.0075 (10)
C7	0.0366 (13)	0.0428 (13)	0.0311 (12)	0.0021 (12)	−0.0043 (10)	−0.0044 (11)
C9	0.0295 (12)	0.0295 (11)	0.0312 (11)	0.0004 (10)	−0.0057 (9)	0.0031 (10)
C8	0.0274 (11)	0.0284 (11)	0.0293 (11)	−0.0003 (10)	0.0012 (9)	0.0001 (9)
C3	0.0486 (15)	0.0338 (12)	0.0349 (12)	−0.0017 (12)	0.0074 (12)	0.0008 (11)
C5	0.0471 (15)	0.0344 (12)	0.0313 (12)	0.0031 (12)	−0.0031 (11)	0.0021 (10)
C4	0.0348 (13)	0.0351 (12)	0.0283 (11)	−0.0023 (11)	−0.0019 (9)	−0.0050 (10)
C2	0.0537 (16)	0.0315 (12)	0.0364 (12)	0.0009 (12)	0.0017 (12)	0.0013 (11)
C6	0.0473 (15)	0.0415 (14)	0.0304 (11)	0.0002 (12)	0.0038 (12)	0.0001 (11)
O2	0.0594 (14)	0.0560 (12)	0.0612 (13)	0.0206 (12)	0.0009 (12)	−0.0009 (11)
O1W	0.0493 (11)	0.0347 (9)	0.0563 (11)	−0.0032 (9)	−0.0051 (9)	−0.0047 (9)

O3—C9	1.255 (3)	C7—H7B	0.9700
N2—C8	1.484 (3)	C9—C8	1.537 (3)
N2—H2A	0.8900	C8—H8	0.9800
N2—H2B	0.8900	C3—C2	1.374 (4)
N2—H2C	0.8900	C3—C4	1.398 (4)
O4—C9	1.243 (3)	C3—H3	0.9300
O1—N1	1.231 (3)	C5—C4	1.384 (3)
C1—C2	1.379 (4)	C5—C6	1.397 (4)
C1—C6	1.382 (4)	C5—H5	0.9300
C1—N1	1.469 (3)	C2—H2	0.9300
N1—O2	1.216 (3)	C6—H6	0.9300
C7—C4	1.511 (3)	O1W—H1WB	0.8502
C7—C8	1.541 (3)	O1W—H1WC	0.8496
C7—H7A	0.9700
C8—N2—H2A	109.5	N2—C8—C7	109.62 (18)
C8—N2—H2B	109.5	C9—C8—C7	112.6 (2)
H2A—N2—H2B	109.5	N2—C8—H8	108.1
C8—N2—H2C	109.5	C9—C8—H8	108.1
H2A—N2—H2C	109.5	C7—C8—H8	108.1
H2B—N2—H2C	109.5	C2—C3—C4	121.3 (2)
C2—C1—C6	121.9 (2)	C2—C3—H3	119.3
C2—C1—N1	118.5 (2)	C4—C3—H3	119.3
C6—C1—N1	119.6 (2)	C4—C5—C6	120.9 (2)
O2—N1—O1	123.5 (3)	C4—C5—H5	119.5
O2—N1—C1	118.5 (2)	C6—C5—H5	119.5
O1—N1—C1	118.0 (2)	C5—C4—C3	118.6 (2)
C4—C7—C8	113.6 (2)	C5—C4—C7	121.9 (2)
C4—C7—H7A	108.8	C3—C4—C7	119.5 (2)
C8—C7—H7A	108.8	C3—C2—C1	118.8 (2)
C4—C7—H7B	108.8	C3—C2—H2	120.6
C8—C7—H7B	108.8	C1—C2—H2	120.6
H7A—C7—H7B	107.7	C1—C6—C5	118.4 (2)
O4—C9—O3	125.8 (2)	C1—C6—H6	120.8
O4—C9—C8	118.6 (2)	C5—C6—H6	120.8
O3—C9—C8	115.5 (2)	H1WB—O1W—H1WC	109.4
N2—C8—C9	110.03 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1W	0.89	1.88	2.760 (3)	168
N2—H2A···O1Wi	0.89	2.43	3.029 (3)	125
N2—H2A···O4ii	0.89	2.29	2.913 (3)	127
N2—H2C···O3iii	0.89	1.92	2.797 (3)	166
O1W—H1WB···O3iv	0.85	2.23	2.764 (3)	121
O1W—H1WC···O4v	0.85	2.00	2.740 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1W	0.89	1.88	2.760 (3)	168
N2—H2A⋯O1Wi	0.89	2.43	3.029 (3)	125
N2—H2A⋯O4ii	0.89	2.29	2.913 (3)	127
N2—H2C⋯O3iii	0.89	1.92	2.797 (3)	166
O1W—H1WB⋯O3iv	0.85	2.23	2.764 (3)	121
O1W—H1WC⋯O4v	0.85	2.00	2.740 (3)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .