Ammonium 2-(2,4-dichloro-phen-oxy)acetate hemihydrate.

The title compound, NH(4) (+)·C(8)H(7)Cl(2)O(6) (-)·0.5H(2)O, was prepared by the reaction of 2-(2,4-dichloro-phen-oxy)-acetic acid and ammonia in water at 367 K. The mol-ecular structure and packing are stabilized by N-H⋯O and O-H⋯O inter-molecular hydrogen-bond inter-actions.

Related literature

For the biological activity of 2-(2,4-dichloro­phen­oxy)acetic acid, see: Lv et al. (1998 ▶). Due to their versatile bonding modes with metal ions, they have also been used in the synthesis of mononuclear monomeric (Gao et al., 2004a ▶; Psomas et al., 2000 ▶) and polymeric complexes (Liu et al., 2004 ▶; Gao et al., 2004b ▶, 2005 ▶).

Experimental

Crystal data

NH4 +·C8H5Cl2O3 −·0.5H2O

M = 247.07

Monoclinic,

a = 37.738 (8) Å

b = 4.3889 (9) Å

c = 12.900 (3) Å

β = 103.83 (3)°

V = 2074.7 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.61 mm−1

T = 293 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

9447 measured reflections

2385 independent reflections

2216 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.060

S = 1.07

2385 reflections

137 parameters

90 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026919/at2826sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026919/at2826Isup2.hkl

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

NH4+·C8H5Cl2O3−·0.5H2O	F(000) = 1016
Mr = 247.07	Dx = 1.582 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2216 reflections
a = 37.738 (8) Å	θ = 3.2–27.5°
b = 4.3889 (9) Å	µ = 0.61 mm−1
c = 12.900 (3) Å	T = 293 K
β = 103.83 (3)°	Bar, colourless
V = 2074.7 (8) Å3	0.15 × 0.12 × 0.10 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	2216 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −48→48
9447 measured reflections	k = −5→5
2385 independent reflections	l = −16→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0294P)2 + 1.6158P] where P = (Fo2 + 2Fc2)/3
2385 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.38 e Å−3
90 restraints	Δρmin = −0.19 e Å−3

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
Cl2	0.252351 (7)	0.68291 (7)	0.14126 (2)	0.01935 (8)
Cl1	0.120306 (7)	0.46470 (7)	0.21755 (2)	0.01934 (8)
O3	0.04445 (2)	−0.21277 (17)	−0.01018 (6)	0.01408 (16)
O2	0.05453 (2)	−0.41964 (18)	−0.15912 (6)	0.01545 (16)
O1	0.10714 (2)	0.10909 (18)	0.02392 (6)	0.01371 (16)
C4	0.14091 (3)	0.2393 (2)	0.04524 (8)	0.0119 (2)
C6	0.18475 (3)	0.5588 (2)	0.16711 (8)	0.0146 (2)
H6A	0.1910	0.6774	0.2285	0.018*
C7	0.09822 (3)	−0.0753 (2)	−0.07012 (8)	0.0122 (2)
H7A	0.1178	−0.2195	−0.0687	0.015*
H7B	0.0961	0.0534	−0.1324	0.015*
C3	0.16595 (3)	0.2075 (2)	−0.01809 (9)	0.0141 (2)
H3A	0.1598	0.0924	−0.0803	0.017*
C8	0.06265 (3)	−0.2485 (2)	−0.07926 (8)	0.0113 (2)
C5	0.15090 (3)	0.4193 (2)	0.13763 (8)	0.0130 (2)
C2	0.20009 (3)	0.3460 (3)	0.01088 (9)	0.0152 (2)
H2A	0.2166	0.3227	−0.0316	0.018*
C1	0.20925 (3)	0.5183 (2)	0.10313 (9)	0.0142 (2)
N1	0.03308 (2)	0.2772 (2)	0.11575 (7)	0.01333 (18)
O1W	0.0000	−0.1574 (3)	0.2500	0.0237 (3)
H1A	0.0399	0.2902	0.1824	0.024 (4)*
H1B	0.0378	0.4414	0.0872	0.024 (4)*
H1WA	−0.0158	−0.2797	0.2154	0.044 (5)*
H1C	0.0093	0.2577	0.0997	0.029 (4)*
H1D	0.0423	0.1190	0.0853	0.029 (4)*

	U11	U22	U33	U12	U13	U23
Cl2	0.01261 (13)	0.02457 (15)	0.02073 (14)	−0.00724 (10)	0.00367 (10)	−0.00251 (10)
Cl1	0.01548 (13)	0.02906 (16)	0.01553 (13)	−0.00433 (11)	0.00777 (10)	−0.00675 (10)
O3	0.0133 (3)	0.0140 (4)	0.0165 (4)	−0.0013 (3)	0.0066 (3)	−0.0002 (3)
O2	0.0164 (4)	0.0157 (4)	0.0137 (4)	−0.0026 (3)	0.0024 (3)	−0.0021 (3)
O1	0.0108 (3)	0.0175 (4)	0.0137 (4)	−0.0038 (3)	0.0047 (3)	−0.0044 (3)
C4	0.0099 (4)	0.0119 (5)	0.0134 (5)	−0.0002 (4)	0.0019 (4)	0.0022 (4)
C6	0.0150 (5)	0.0155 (5)	0.0125 (5)	−0.0014 (4)	0.0013 (4)	−0.0006 (4)
C7	0.0119 (5)	0.0132 (5)	0.0121 (5)	−0.0014 (4)	0.0042 (4)	−0.0020 (4)
C3	0.0137 (5)	0.0150 (5)	0.0140 (5)	−0.0012 (4)	0.0040 (4)	−0.0013 (4)
C8	0.0101 (4)	0.0101 (4)	0.0130 (5)	0.0014 (4)	0.0016 (4)	0.0033 (4)
C5	0.0125 (5)	0.0154 (5)	0.0121 (5)	0.0007 (4)	0.0048 (4)	0.0012 (4)
C2	0.0130 (5)	0.0171 (5)	0.0170 (5)	−0.0006 (4)	0.0064 (4)	0.0010 (4)
C1	0.0102 (5)	0.0151 (5)	0.0167 (5)	−0.0028 (4)	0.0019 (4)	0.0021 (4)
N1	0.0131 (4)	0.0134 (4)	0.0143 (4)	−0.0009 (3)	0.0050 (3)	0.0001 (3)
O1W	0.0199 (6)	0.0128 (5)	0.0358 (7)	0.000	0.0014 (5)	0.000

Cl2—C1	1.7400 (11)	C7—H7A	0.9700
Cl1—C5	1.7336 (12)	C7—H7B	0.9700
O3—C8	1.2584 (13)	C3—C2	1.3924 (15)
O2—C8	1.2523 (13)	C3—H3A	0.9300
O1—C4	1.3635 (13)	C2—C1	1.3824 (16)
O1—C7	1.4298 (12)	C2—H2A	0.9300
C4—C3	1.3962 (15)	N1—H1A	0.8385
C4—C5	1.4042 (15)	N1—H1B	0.8474
C6—C5	1.3851 (15)	N1—H1C	0.8757
C6—C1	1.3901 (16)	N1—H1D	0.9069
C6—H6A	0.9300	O1W—H1WA	0.8458
C7—C8	1.5225 (14)
C4—O1—C7	115.30 (8)	O2—C8—C7	113.65 (9)
O1—C4—C3	124.81 (10)	O3—C8—C7	120.22 (9)
O1—C4—C5	117.10 (9)	C6—C5—C4	121.65 (10)
C3—C4—C5	118.09 (10)	C6—C5—Cl1	119.18 (8)
C5—C6—C1	118.74 (10)	C4—C5—Cl1	119.17 (8)
C5—C6—H6A	120.6	C1—C2—C3	119.65 (10)
C1—C6—H6A	120.6	C1—C2—H2A	120.2
O1—C7—C8	111.88 (9)	C3—C2—H2A	120.2
O1—C7—H7A	109.2	C2—C1—C6	121.08 (10)
C8—C7—H7A	109.2	C2—C1—Cl2	119.67 (9)
O1—C7—H7B	109.2	C6—C1—Cl2	119.24 (9)
C8—C7—H7B	109.2	H1A—N1—H1B	110.0
H7A—C7—H7B	107.9	H1A—N1—H1C	107.2
C2—C3—C4	120.77 (10)	H1B—N1—H1C	106.9
C2—C3—H3A	119.6	H1A—N1—H1D	116.2
C4—C3—H3A	119.6	H1B—N1—H1D	108.7
O2—C8—O3	126.13 (10)	H1C—N1—H1D	107.5

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O2i	0.85	1.97	3.2969 (15)	169.9
N1—H1A···O2i	0.84	2.07	2.8908 (14)	168
N1—H1B···O3ii	0.85	2.02	2.8578 (13)	168
N1—H1C···O3iii	0.88	2.09	2.9310 (15)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O2i	0.85	1.97	3.2969 (15)	170
N1—H1A⋯O2i	0.84	2.07	2.8908 (14)	168
N1—H1B⋯O3ii	0.85	2.02	2.8578 (13)	168
N1—H1C⋯O3iii	0.88	2.09	2.9310 (15)	161

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