4-Ethyl-anilinium 2-carb-oxy-acetate.

In the crystal structure of the title compound, C(8)H(12)N(+)·C(3)H(3)O(4) (-), the hydrogen malonate anions are linked into infinite chains parallel to the b axis by inter-molecular O-H⋯O hydrogen bonds of the type COO(-)⋯HO(2)C in a head-to-tail fashion. The 4-ethyl-anilinium cations link adjacent anion chains by inter-molecular N-H⋯O hydrogen bonds into a two-dimensional network parallel to the b and c axes.

Related literature

For background to mol­ecular–ionic compounds, see: Czupiński et al. (2002 ▶); Katrusiak & Szafrański (2006 ▶); Chen (2009 ▶); Wang (2010 ▶).

Experimental

Crystal data

C8H12N+·C3H3O4 −

M = 225.24

Monoclinic,

a = 13.439 (3) Å

b = 9.2914 (19) Å

c = 8.8827 (18) Å

β = 99.177 (10)°

V = 1095.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 291 K

0.36 × 0.32 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.963, T max = 0.971

11013 measured reflections

2510 independent reflections

1995 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.161

S = 1.05

2510 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.43 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810029648/kj2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029648/kj2151Isup2.hkl

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

C8H12N+·C3H3O4−	F(000) = 480
Mr = 225.24	Dx = 1.366 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9421 reflections
a = 13.439 (3) Å	θ = 3.1–27.6°
b = 9.2914 (19) Å	µ = 0.10 mm−1
c = 8.8827 (18) Å	T = 291 K
β = 99.177 (10)°	Block, colorless
V = 1095.0 (4) Å3	0.36 × 0.32 × 0.28 mm
Z = 4

Rigaku SCXmini diffractometer	2510 independent reflections
Radiation source: fine-focus sealed tube	1995 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.963, Tmax = 0.971	l = −11→11
11013 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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0682P)2 + 0.8364P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2510 reflections	Δρmax = 0.42 e Å−3
147 parameters	Δρmin = −0.43 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (5)

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
C1	0.90859 (14)	0.4455 (2)	0.0928 (2)	0.0260 (4)
C2	0.89084 (16)	0.3160 (2)	−0.0141 (2)	0.0290 (5)
H2A	0.8213	0.3177	−0.0645	0.035*
H2B	0.9332	0.3261	−0.0923	0.035*
C3	0.91163 (15)	0.1717 (2)	0.0613 (2)	0.0265 (4)
C4	0.3837 (2)	0.7987 (4)	0.3598 (4)	0.0718 (10)
H4A	0.3281	0.7797	0.4124	0.108*
H4B	0.3704	0.7573	0.2595	0.108*
H4C	0.3926	0.9008	0.3517	0.108*
C5	0.4769 (2)	0.7341 (4)	0.4458 (3)	0.0605 (8)
H5A	0.4657	0.6316	0.4555	0.073*
H5B	0.4877	0.7745	0.5478	0.073*
C6	0.57213 (18)	0.7548 (3)	0.3778 (3)	0.0405 (6)
C7	0.63668 (19)	0.6409 (3)	0.3677 (3)	0.0442 (6)
H7A	0.6205	0.5508	0.4025	0.053*
C8	0.72484 (18)	0.6569 (2)	0.3073 (3)	0.0388 (5)
H8A	0.7669	0.5785	0.3006	0.047*
C9	0.74915 (15)	0.7901 (2)	0.2574 (2)	0.0300 (5)
C10	0.68750 (17)	0.9066 (2)	0.2664 (3)	0.0388 (5)
H10A	0.7046	0.9967	0.2328	0.047*
C11	0.59904 (19)	0.8877 (3)	0.3267 (3)	0.0453 (6)
H11A	0.5570	0.9662	0.3327	0.054*
N1	0.84388 (13)	0.80909 (19)	0.1986 (2)	0.0347 (5)
H1A	0.8755	0.7249	0.1992	0.052*
H1B	0.8828	0.8714	0.2571	0.052*
H1C	0.8311	0.8426	0.1036	0.052*
O1	0.88090 (13)	0.56380 (16)	0.03767 (19)	0.0412 (4)
O2	0.95091 (12)	0.42353 (15)	0.22859 (17)	0.0352 (4)
O3	0.84347 (12)	0.08947 (16)	0.0783 (2)	0.0413 (4)
O4	1.00669 (11)	0.14348 (15)	0.10516 (18)	0.0337 (4)
H4	1.0153	0.0579	0.1549	0.105 (14)*

	U11	U22	U33	U12	U13	U23
C1	0.0251 (9)	0.0210 (9)	0.0323 (10)	−0.0010 (7)	0.0058 (8)	0.0015 (7)
C2	0.0335 (11)	0.0246 (10)	0.0277 (10)	−0.0018 (8)	0.0011 (8)	0.0019 (8)
C3	0.0333 (11)	0.0210 (9)	0.0261 (10)	−0.0025 (8)	0.0072 (8)	−0.0048 (7)
C4	0.0498 (17)	0.083 (2)	0.088 (2)	−0.0032 (16)	0.0301 (17)	0.0124 (19)
C5	0.0609 (18)	0.071 (2)	0.0559 (17)	0.0003 (15)	0.0279 (14)	0.0118 (15)
C6	0.0422 (13)	0.0461 (14)	0.0340 (11)	−0.0037 (10)	0.0088 (10)	0.0026 (10)
C7	0.0531 (15)	0.0344 (12)	0.0463 (14)	−0.0079 (11)	0.0117 (11)	0.0074 (10)
C8	0.0417 (13)	0.0267 (11)	0.0481 (13)	−0.0004 (9)	0.0074 (10)	0.0040 (9)
C9	0.0277 (10)	0.0285 (10)	0.0316 (10)	−0.0039 (8)	−0.0019 (8)	−0.0002 (8)
C10	0.0370 (12)	0.0269 (11)	0.0514 (14)	−0.0021 (9)	0.0037 (10)	0.0037 (9)
C11	0.0422 (13)	0.0398 (13)	0.0543 (15)	0.0065 (10)	0.0091 (11)	0.0003 (11)
N1	0.0280 (9)	0.0244 (9)	0.0497 (11)	−0.0017 (7)	0.0003 (8)	0.0051 (8)
O1	0.0511 (10)	0.0242 (8)	0.0454 (9)	0.0081 (7)	−0.0010 (7)	0.0041 (7)
O2	0.0499 (9)	0.0225 (7)	0.0305 (8)	0.0008 (6)	−0.0021 (7)	−0.0014 (6)
O3	0.0363 (9)	0.0264 (8)	0.0626 (11)	−0.0054 (6)	0.0118 (8)	0.0058 (7)
O4	0.0328 (8)	0.0222 (7)	0.0445 (9)	−0.0023 (6)	0.0010 (6)	0.0024 (6)

C1—O1	1.237 (2)	C6—C7	1.381 (4)
C1—O2	1.265 (2)	C6—C11	1.383 (3)
C1—C2	1.528 (3)	C7—C8	1.384 (3)
C2—C3	1.505 (3)	C7—H7A	0.9300
C2—H2A	0.9700	C8—C9	1.372 (3)
C2—H2B	0.9700	C8—H8A	0.9300
C3—O3	1.220 (2)	C9—C10	1.373 (3)
C3—O4	1.301 (2)	C9—N1	1.462 (3)
C4—C5	1.485 (5)	C10—C11	1.390 (3)
C4—H4A	0.9600	C10—H10A	0.9300
C4—H4B	0.9600	C11—H11A	0.9300
C4—H4C	0.9600	N1—H1A	0.8900
C5—C6	1.512 (4)	N1—H1B	0.8900
C5—H5A	0.9700	N1—H1C	0.8900
C5—H5B	0.9700	O4—H4	0.9084
O1—C1—O2	125.59 (19)	C7—C6—C5	120.6 (2)
O1—C1—C2	116.51 (18)	C11—C6—C5	121.8 (2)
O2—C1—C2	117.89 (17)	C6—C7—C8	121.9 (2)
C3—C2—C1	115.15 (16)	C6—C7—H7A	119.1
C3—C2—H2A	108.5	C8—C7—H7A	119.1
C1—C2—H2A	108.5	C9—C8—C7	119.0 (2)
C3—C2—H2B	108.5	C9—C8—H8A	120.5
C1—C2—H2B	108.5	C7—C8—H8A	120.5
H2A—C2—H2B	107.5	C8—C9—C10	121.0 (2)
O3—C3—O4	123.86 (19)	C8—C9—N1	119.35 (19)
O3—C3—C2	121.53 (19)	C10—C9—N1	119.61 (19)
O4—C3—C2	114.60 (17)	C9—C10—C11	119.0 (2)
C5—C4—H4A	109.5	C9—C10—H10A	120.5
C5—C4—H4B	109.5	C11—C10—H10A	120.5
H4A—C4—H4B	109.5	C6—C11—C10	121.6 (2)
C5—C4—H4C	109.5	C6—C11—H11A	119.2
H4A—C4—H4C	109.5	C10—C11—H11A	119.2
H4B—C4—H4C	109.5	C9—N1—H1A	109.5
C4—C5—C6	116.2 (2)	C9—N1—H1B	109.5
C4—C5—H5A	108.2	H1A—N1—H1B	109.5
C6—C5—H5A	108.2	C9—N1—H1C	109.5
C4—C5—H5B	108.2	H1A—N1—H1C	109.5
C6—C5—H5B	108.2	H1B—N1—H1C	109.5
H5A—C5—H5B	107.4	C3—O4—H4	111.3
C7—C6—C11	117.6 (2)
O1—C1—C2—C3	−171.71 (18)	C6—C7—C8—C9	0.6 (4)
O2—C1—C2—C3	9.0 (3)	C7—C8—C9—C10	−0.1 (3)
C1—C2—C3—O3	108.1 (2)	C7—C8—C9—N1	177.8 (2)
C1—C2—C3—O4	−72.1 (2)	C8—C9—C10—C11	−0.3 (3)
C4—C5—C6—C7	−134.2 (3)	N1—C9—C10—C11	−178.2 (2)
C4—C5—C6—C11	47.1 (4)	C7—C6—C11—C10	0.3 (4)
C11—C6—C7—C8	−0.7 (4)	C5—C6—C11—C10	179.0 (2)
C5—C6—C7—C8	−179.4 (3)	C9—C10—C11—C6	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.89	2.08	2.777 (2)	134
N1—H1B···O1i	0.89	2.57	3.200 (3)	129
N1—H1B···O2ii	0.89	2.27	2.930 (2)	131
N1—H1C···O3iii	0.89	2.31	2.815 (2)	116
N1—H1A···O4ii	0.89	2.28	2.885 (2)	125
O4—H4···O2iv	0.91	1.64	2.532 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.89	2.08	2.777 (2)	134
N1—H1B⋯O1i	0.89	2.57	3.200 (3)	129
N1—H1B⋯O2ii	0.89	2.27	2.930 (2)	131
N1—H1C⋯O3iii	0.89	2.31	2.815 (2)	116
N1—H1A⋯O4ii	0.89	2.28	2.885 (2)	125
O4—H4⋯O2iv	0.91	1.64	2.532 (2)	167

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