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 amine group. The crystal packing is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, building sheets parallel to the (001) plane.

Related literature

For details on 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

Monoclinic,

a = 6.2349 (12) Å

b = 5.2990 (11) Å

c = 15.727 (3) Å

β = 101.40 (3)°

V = 509.35 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 (2) K

0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.964, T max = 0.982

5388 measured reflections

1297 independent reflections

1184 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 1.14

1297 reflections

153 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.34 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/S1600536808017960/rz2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017960/rz2221Isup2.hkl

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

C9H10N2O4·H2O	F000 = 240
Mr = 228.21	Dx = 1.488 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1458 reflections
a = 6.2349 (12) Å	θ = 3.3–27.5º
b = 5.2990 (11) Å	µ = 0.12 mm−1
c = 15.727 (3) Å	T = 293 (2) K
β = 101.40 (3)º	Block, colourless
V = 509.35 (18) Å3	0.30 × 0.25 × 0.15 mm
Z = 2

Rigaku Mercury2 (2x2 bin mode) diffractometer	1297 independent reflections
Radiation source: fine-focus sealed tube	1184 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.3º
ω scans	h = −8→8
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −6→6
Tmin = 0.964, Tmax = 0.982	l = −20→19
5388 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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0664P)2 + 0.2902P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
1297 reflections	Δρmax = 0.36 e Å−3
153 parameters	Δρmin = −0.34 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
O1	0.3398 (5)	0.1706 (7)	0.0174 (2)	0.0512 (9)
N2	0.2068 (5)	−0.9188 (6)	0.41031 (19)	0.0286 (7)
H2A	0.2056	−1.0468	0.3736	0.043*
H2B	0.0991	−0.9385	0.4394	0.043*
H2D	0.3345	−0.9154	0.4475	0.043*
O3	−0.0544 (4)	−0.3216 (6)	0.34808 (17)	0.0342 (6)
C1	0.3833 (6)	−0.1391 (8)	0.1227 (2)	0.0283 (8)
C7	0.1506 (6)	−0.7322 (7)	0.2635 (2)	0.0301 (8)
H7A	0.2309	−0.8847	0.2560	0.036*
H7B	−0.0026	−0.7631	0.2392	0.036*
O4	−0.1341 (4)	−0.6381 (6)	0.42852 (18)	0.0367 (7)
O2	0.6547 (5)	0.1366 (7)	0.1010 (2)	0.0537 (9)
C5	0.4472 (6)	−0.4434 (9)	0.2352 (2)	0.0346 (9)
H5A	0.5413	−0.5221	0.2807	0.042*
C9	−0.0204 (5)	−0.5355 (7)	0.3814 (2)	0.0243 (7)
C2	0.1690 (6)	−0.2143 (9)	0.0984 (2)	0.0335 (9)
H2C	0.0766	−0.1372	0.0520	0.040*
C3	0.0930 (6)	−0.4068 (9)	0.1441 (2)	0.0330 (8)
H3A	−0.0516	−0.4600	0.1282	0.040*
N1	0.4628 (5)	0.0705 (7)	0.0771 (2)	0.0351 (8)
C8	0.1756 (5)	−0.6791 (7)	0.3613 (2)	0.0231 (7)
H8A	0.3065	−0.5751	0.3798	0.028*
C6	0.5246 (6)	−0.2510 (9)	0.1903 (2)	0.0334 (9)
H6A	0.6694	−0.1982	0.2055	0.040*
C4	0.2310 (6)	−0.5208 (8)	0.2133 (2)	0.0281 (7)
O5	0.6393 (5)	−1.0768 (7)	0.4286 (2)	0.0412 (7)
H30	0.715 (8)	−0.930 (12)	0.427 (3)	0.047 (14)*
H31	0.681 (11)	−1.158 (18)	0.393 (4)	0.08 (2)*

	U11	U22	U33	U12	U13	U23
O1	0.0582 (19)	0.050 (2)	0.0455 (16)	0.0021 (17)	0.0115 (14)	0.0193 (17)
N2	0.0280 (14)	0.0290 (16)	0.0305 (14)	0.0084 (13)	0.0095 (11)	0.0063 (14)
O3	0.0334 (13)	0.0275 (14)	0.0409 (14)	0.0068 (12)	0.0057 (11)	0.0025 (13)
C1	0.0351 (17)	0.0278 (19)	0.0241 (15)	−0.0002 (15)	0.0111 (13)	−0.0019 (15)
C7	0.0401 (19)	0.0273 (19)	0.0246 (16)	−0.0030 (16)	0.0109 (14)	−0.0022 (15)
O4	0.0374 (14)	0.0334 (15)	0.0452 (14)	0.0024 (13)	0.0223 (12)	−0.0027 (13)
O2	0.0545 (19)	0.051 (2)	0.0563 (18)	−0.0224 (17)	0.0128 (15)	0.0021 (17)
C5	0.0274 (17)	0.044 (2)	0.0313 (17)	0.0054 (18)	0.0037 (14)	0.0094 (18)
C9	0.0244 (15)	0.0246 (17)	0.0231 (14)	0.0003 (14)	0.0031 (12)	−0.0061 (14)
C2	0.0333 (18)	0.041 (2)	0.0249 (16)	0.0008 (17)	0.0024 (14)	0.0034 (17)
C3	0.0320 (17)	0.040 (2)	0.0263 (16)	−0.0036 (18)	0.0037 (14)	−0.0015 (17)
N1	0.0443 (18)	0.0350 (18)	0.0289 (15)	−0.0024 (17)	0.0143 (14)	−0.0004 (14)
C8	0.0263 (15)	0.0180 (16)	0.0255 (15)	0.0014 (13)	0.0064 (12)	0.0012 (13)
C6	0.0229 (16)	0.045 (2)	0.0330 (17)	−0.0026 (16)	0.0071 (13)	0.0041 (18)
C4	0.0327 (17)	0.0298 (18)	0.0238 (15)	0.0028 (16)	0.0103 (13)	−0.0024 (16)
O5	0.0308 (14)	0.0402 (19)	0.0557 (18)	0.0035 (14)	0.0160 (13)	−0.0028 (15)

O1—N1	1.211 (4)	O2—N1	1.232 (4)
N2—C8	1.478 (5)	C5—C4	1.385 (5)
N2—H2A	0.8900	C5—C6	1.381 (6)
N2—H2B	0.8900	C5—H5A	0.9300
N2—H2D	0.8900	C9—C8	1.524 (5)
O3—C9	1.249 (5)	C2—C3	1.384 (6)
C1—C6	1.374 (5)	C2—H2C	0.9300
C1—C2	1.374 (5)	C3—C4	1.387 (5)
C1—N1	1.461 (5)	C3—H3A	0.9300
C7—C4	1.512 (5)	C8—H8A	0.9800
C7—C8	1.541 (4)	C6—H6A	0.9300
C7—H7A	0.9700	O5—H30	0.92 (6)
C7—H7B	0.9700	O5—H31	0.79 (8)
O4—C9	1.247 (4)
C8—N2—H2A	109.5	C1—C2—H2C	120.5
C8—N2—H2B	109.5	C3—C2—H2C	120.5
H2A—N2—H2B	109.5	C2—C3—C4	120.4 (3)
C8—N2—H2D	109.5	C2—C3—H3A	119.8
H2A—N2—H2D	109.5	C4—C3—H3A	119.8
H2B—N2—H2D	109.5	O1—N1—O2	122.7 (4)
C6—C1—C2	122.0 (4)	O1—N1—C1	119.3 (3)
C6—C1—N1	118.7 (3)	O2—N1—C1	118.0 (3)
C2—C1—N1	119.3 (3)	N2—C8—C9	110.4 (3)
C4—C7—C8	114.0 (3)	N2—C8—C7	109.9 (3)
C4—C7—H7A	108.7	C9—C8—C7	111.7 (3)
C8—C7—H7A	108.7	N2—C8—H8A	108.2
C4—C7—H7B	108.7	C9—C8—H8A	108.2
C8—C7—H7B	108.7	C7—C8—H8A	108.2
H7A—C7—H7B	107.6	C1—C6—C5	118.6 (3)
C4—C5—C6	120.9 (3)	C1—C6—H6A	120.7
C4—C5—H5A	119.6	C5—C6—H6A	120.7
C6—C5—H5A	119.6	C5—C4—C3	119.2 (4)
O4—C9—O3	125.1 (3)	C5—C4—C7	119.8 (3)
O4—C9—C8	118.6 (3)	C3—C4—C7	121.0 (3)
O3—C9—C8	116.3 (3)	H30—O5—H31	101 (6)
C1—C2—C3	118.9 (3)
C6—C1—C2—C3	0.7 (6)	C4—C7—C8—N2	−150.5 (3)
N1—C1—C2—C3	−177.6 (3)	C4—C7—C8—C9	86.6 (4)
C1—C2—C3—C4	0.2 (6)	C2—C1—C6—C5	−0.5 (6)
C6—C1—N1—O1	180.0 (4)	N1—C1—C6—C5	177.8 (4)
C2—C1—N1—O1	−1.7 (5)	C4—C5—C6—C1	−0.7 (6)
C6—C1—N1—O2	0.6 (5)	C6—C5—C4—C3	1.6 (6)
C2—C1—N1—O2	178.9 (4)	C6—C5—C4—C7	179.9 (4)
O4—C9—C8—N2	−4.9 (4)	C2—C3—C4—C5	−1.3 (6)
O3—C9—C8—N2	175.4 (3)	C2—C3—C4—C7	−179.6 (3)
O4—C9—C8—C7	117.7 (4)	C8—C7—C4—C5	59.3 (5)
O3—C9—C8—C7	−61.9 (4)	C8—C7—C4—C3	−122.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.89	2.16	2.745 (4)	123
N2—H2B···O4ii	0.89	2.30	2.904 (4)	125
O5—H30···O4iii	0.92 (6)	1.81 (6)	2.721 (5)	177 (5)
O5—H31···O3iv	0.79 (8)	2.11 (8)	2.809 (4)	148 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.89	2.16	2.745 (4)	123
N2—H2B⋯O4ii	0.89	2.30	2.904 (4)	125
O5—H30⋯O4iii	0.92 (6)	1.81 (6)	2.721 (5)	177 (5)
O5—H31⋯O3iv	0.79 (8)	2.11 (8)	2.809 (4)	148 (6)

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