3-[(3,4-Dichloro-phen-yl)amino-carbon-yl]propionic acid monohydrate.

In the crystal structure of the title compound, C(10)H(9)Cl(2)NO(3)·H(2)O, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to the H atoms of adjacent -CH(2) groups. In the crystal, the mol-ecules are linked into a three-dimensional network through N-H⋯O and O-H⋯O inter-molecular hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2009 ▶). For hydrogen bonds involving carboxylic acids, see: Jagannathan et al. (1994 ▶); Leiserowitz (1976 ▶). For the modeling of water H atoms, see: Nardelli (1999 ▶).

Experimental

Crystal data

C10H9Cl2NO3·H2O

M = 280.10

Monoclinic,

a = 9.5634 (9) Å

b = 7.4527 (7) Å

c = 17.292 (2) Å

β = 104.35 (2)°

V = 1194.0 (2) Å3

Z = 4

Cu Kα radiation

μ = 4.95 mm−1

T = 299 K

0.55 × 0.50 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.098, T max = 0.138

2508 measured reflections

2129 independent reflections

2052 reflections with I > 2σ(I)

R int = 0.072

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.212

S = 1.08

2129 reflections

167 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.92 e Å−3

Δρmin = −0.69 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024519/ci2838sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024519/ci2838Isup2.hkl

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

C10H9Cl2NO3·H2O	F(000) = 576
Mr = 280.10	Dx = 1.558 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.5634 (9) Å	θ = 4.8–20.7°
b = 7.4527 (7) Å	µ = 4.95 mm−1
c = 17.292 (2) Å	T = 299 K
β = 104.35 (2)°	Prism, colourless
V = 1194.0 (2) Å3	0.55 × 0.50 × 0.40 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2052 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.072
graphite	θmax = 67.0°, θmin = 4.8°
ω/2θ scans	h = −11→1
Absorption correction: ψ scan (North et al., 1968)	k = −8→0
Tmin = 0.098, Tmax = 0.138	l = −19→20
2508 measured reflections	3 standard reflections every 120 min
2129 independent reflections	intensity decay: 1.0%

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)] = 0.083	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.212	w = 1/[σ2(Fo2) + (0.1684P)2 + 0.6399P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.003
2129 reflections	Δρmax = 0.92 e Å−3
167 parameters	Δρmin = −0.69 e Å−3
5 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: 0.014 (2)

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
Cl1	−0.35278 (8)	0.10598 (12)	0.56662 (5)	0.0441 (4)
Cl2	−0.33021 (8)	0.03602 (12)	0.38996 (4)	0.0449 (4)
O1	0.1190 (2)	0.2952 (3)	0.33626 (13)	0.0417 (6)
O2	0.5845 (3)	0.4233 (4)	0.26373 (15)	0.0534 (7)
H2O	0.674 (4)	0.448 (6)	0.262 (3)	0.064*
O3	0.6264 (3)	0.5188 (4)	0.38871 (15)	0.0543 (7)
N1	0.1755 (3)	0.3197 (3)	0.47092 (15)	0.0331 (6)
H1N	0.240 (4)	0.353 (5)	0.511 (2)	0.040*
C1	0.0452 (3)	0.2667 (4)	0.48923 (17)	0.0301 (7)
C2	0.0368 (3)	0.2923 (4)	0.56697 (18)	0.0345 (7)
H2	0.1138	0.3446	0.6036	0.041*
C3	−0.0840 (3)	0.2416 (4)	0.59077 (18)	0.0367 (7)
H3	−0.0879	0.2582	0.6435	0.044*
C4	−0.2005 (3)	0.1652 (4)	0.53626 (17)	0.0319 (7)
C5	−0.1905 (3)	0.1364 (4)	0.45895 (17)	0.0315 (7)
C6	−0.0693 (3)	0.1877 (4)	0.43433 (17)	0.0325 (7)
H6	−0.0646	0.1696	0.3818	0.039*
C7	0.2060 (3)	0.3302 (4)	0.39971 (17)	0.0311 (7)
C8	0.3601 (3)	0.3889 (4)	0.40446 (18)	0.0360 (7)
H8A	0.3773	0.5034	0.4319	0.043*
H8B	0.4260	0.3022	0.4359	0.043*
C9	0.3923 (4)	0.4068 (7)	0.3247 (2)	0.0566 (11)
H9A	0.3294	0.4973	0.2939	0.068*
H9B	0.3717	0.2938	0.2963	0.068*
C10	0.5465 (3)	0.4577 (5)	0.33053 (19)	0.0400 (8)
O4	0.1421 (3)	0.9875 (5)	0.23932 (16)	0.0570 (8)
H41	0.070 (4)	0.945 (6)	0.209 (3)	0.068*
H42	0.116 (5)	1.059 (6)	0.271 (3)	0.068*

	U11	U22	U33	U12	U13	U23
Cl1	0.0340 (5)	0.0587 (6)	0.0425 (6)	−0.0077 (3)	0.0149 (4)	0.0020 (3)
Cl2	0.0329 (5)	0.0645 (7)	0.0332 (6)	−0.0134 (3)	0.0003 (4)	−0.0034 (3)
O1	0.0306 (11)	0.0668 (15)	0.0259 (11)	−0.0049 (10)	0.0035 (9)	−0.0020 (9)
O2	0.0391 (13)	0.0936 (19)	0.0297 (13)	−0.0109 (13)	0.0123 (10)	0.0014 (12)
O3	0.0375 (13)	0.0839 (19)	0.0395 (14)	−0.0159 (13)	0.0058 (11)	−0.0119 (13)
N1	0.0270 (12)	0.0455 (14)	0.0256 (13)	−0.0077 (10)	0.0045 (10)	−0.0018 (10)
C1	0.0263 (13)	0.0343 (14)	0.0291 (15)	0.0006 (10)	0.0057 (11)	0.0034 (11)
C2	0.0326 (15)	0.0411 (15)	0.0279 (15)	−0.0056 (12)	0.0039 (12)	−0.0048 (11)
C3	0.0392 (16)	0.0438 (16)	0.0281 (15)	−0.0024 (12)	0.0103 (12)	−0.0045 (12)
C4	0.0273 (14)	0.0380 (14)	0.0310 (14)	−0.0010 (11)	0.0085 (11)	0.0037 (11)
C5	0.0265 (14)	0.0372 (14)	0.0272 (14)	−0.0027 (11)	−0.0001 (11)	0.0022 (11)
C6	0.0313 (14)	0.0417 (16)	0.0237 (14)	−0.0022 (11)	0.0055 (11)	0.0017 (11)
C7	0.0255 (14)	0.0359 (14)	0.0301 (14)	0.0002 (11)	0.0039 (11)	0.0017 (11)
C8	0.0299 (15)	0.0489 (17)	0.0288 (16)	−0.0071 (12)	0.0063 (12)	0.0003 (12)
C9	0.0322 (18)	0.110 (3)	0.0274 (17)	−0.0167 (18)	0.0062 (13)	−0.0016 (17)
C10	0.0315 (16)	0.060 (2)	0.0281 (15)	−0.0061 (13)	0.0071 (12)	0.0040 (13)
O4	0.0364 (13)	0.094 (2)	0.0387 (14)	−0.0004 (13)	0.0064 (11)	−0.0163 (14)

Cl1—C4	1.723 (3)	C3—H3	0.93
Cl2—C5	1.726 (3)	C4—C5	1.381 (4)
O1—C7	1.229 (4)	C5—C6	1.384 (4)
O2—C10	1.319 (4)	C6—H6	0.93
O2—H2O	0.88 (3)	C7—C8	1.520 (4)
O3—C10	1.193 (4)	C8—C9	1.492 (5)
N1—C7	1.337 (4)	C8—H8A	0.97
N1—C1	1.415 (4)	C8—H8B	0.97
N1—H1N	0.84 (3)	C9—C10	1.501 (4)
C1—C2	1.380 (4)	C9—H9A	0.97
C1—C6	1.390 (4)	C9—H9B	0.97
C2—C3	1.372 (4)	O4—H41	0.82 (3)
C2—H2	0.93	O4—H42	0.84 (3)
C3—C4	1.390 (4)
C10—O2—H2O	118 (3)	C1—C6—H6	120.5
C7—N1—C1	128.9 (2)	O1—C7—N1	123.8 (3)
C7—N1—H1N	117 (3)	O1—C7—C8	122.8 (3)
C1—N1—H1N	114 (3)	N1—C7—C8	113.4 (3)
C2—C1—C6	119.8 (3)	C9—C8—C7	113.3 (3)
C2—C1—N1	116.5 (3)	C9—C8—H8A	108.9
C6—C1—N1	123.6 (3)	C7—C8—H8A	108.9
C3—C2—C1	120.7 (3)	C9—C8—H8B	108.9
C3—C2—H2	119.6	C7—C8—H8B	108.9
C1—C2—H2	119.6	H8A—C8—H8B	107.7
C2—C3—C4	120.2 (3)	C8—C9—C10	112.6 (3)
C2—C3—H3	119.9	C8—C9—H9A	109.1
C4—C3—H3	119.9	C10—C9—H9A	109.1
C5—C4—C3	118.9 (3)	C8—C9—H9B	109.1
C5—C4—Cl1	121.4 (2)	C10—C9—H9B	109.1
C3—C4—Cl1	119.6 (2)	H9A—C9—H9B	107.8
C4—C5—C6	121.3 (3)	O3—C10—O2	123.7 (3)
C4—C5—Cl2	120.6 (2)	O3—C10—C9	124.5 (3)
C6—C5—Cl2	118.1 (2)	O2—C10—C9	111.8 (3)
C5—C6—C1	119.0 (3)	H41—O4—H42	109 (4)
C5—C6—H6	120.5
C7—N1—C1—C2	−171.2 (3)	C4—C5—C6—C1	1.2 (4)
C7—N1—C1—C6	10.6 (5)	Cl2—C5—C6—C1	−179.2 (2)
C6—C1—C2—C3	−0.3 (5)	C2—C1—C6—C5	0.1 (4)
N1—C1—C2—C3	−178.6 (3)	N1—C1—C6—C5	178.3 (3)
C1—C2—C3—C4	−0.8 (5)	C1—N1—C7—O1	1.1 (5)
C2—C3—C4—C5	2.1 (5)	C1—N1—C7—C8	−178.6 (3)
C2—C3—C4—Cl1	−178.8 (3)	O1—C7—C8—C9	2.4 (5)
C3—C4—C5—C6	−2.3 (4)	N1—C7—C8—C9	−177.9 (3)
Cl1—C4—C5—C6	178.6 (2)	C7—C8—C9—C10	−177.7 (3)
C3—C4—C5—Cl2	178.1 (2)	C8—C9—C10—O3	−16.9 (6)
Cl1—C4—C5—Cl2	−1.0 (4)	C8—C9—C10—O2	161.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O4i	0.88 (3)	1.79 (3)	2.672 (4)	177 (5)
N1—H1N···O3ii	0.84 (3)	2.11 (3)	2.941 (4)	168 (4)
O4—H41···O1iii	0.82 (3)	2.11 (4)	2.894 (4)	162 (5)
O4—H42···O1iv	0.84 (3)	2.09 (3)	2.881 (4)	156 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O4i	0.88 (3)	1.79 (3)	2.672 (4)	177 (5)
N1—H1N⋯O3ii	0.84 (3)	2.11 (3)	2.941 (4)	168 (4)
O4—H41⋯O1iii	0.82 (3)	2.11 (4)	2.894 (4)	162 (5)
O4—H42⋯O1iv	0.84 (3)	2.09 (3)	2.881 (4)	156 (5)

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