4-(2-Hydroxy-ethyl)anilinium 3,5-dinitro-benzoate.

In the title compound, C(8)H(12)NO(+)·C(7)H(3)N(2)O(6) (-), the anilinium and hydroxyl protons of the cation result in N-H⋯O, N-H⋯(O,O) and O-H⋯O hydrogen-bonding inter-actions with carboxyl-ate O-atom acceptors, forming a two-dimensional network structure. An intermolecular C-H⋯O interaction is also present.

Related literature

For related structures, see: Etter & Frankenbach (1989 ▶); Lynch et al. (1991a ▶,b ▶, 1992 ▶, 1993 ▶); Ranganathan & Pedireddi (1998 ▶); Aakeröy et al. (2003 ▶); Hosomi et al. (2000 ▶).

Experimental

Crystal data

C8H12NO+·C7H3N2O6 −

M = 349.30

Monoclinic,

a = 15.9566 (19) Å

b = 5.7844 (5) Å

c = 17.4118 (14) Å

β = 102.811 (10)°

V = 1567.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 297 K

0.30 × 0.30 × 0.25 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.950, T max = 0.980

5928 measured reflections

3061 independent reflections

2203 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.099

S = 0.98

3061 reflections

242 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030426/bt5012sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030426/bt5012Isup2.hkl

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

C8H12NO+·C7H3N2O6−	F(000) = 728
Mr = 349.30	Dx = 1.480 Mg m−3
Monoclinic, P21/n	Melting point: 389 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 15.9566 (19) Å	Cell parameters from 3103 reflections
b = 5.7844 (5) Å	θ = 3.0–28.9°
c = 17.4118 (14) Å	µ = 0.12 mm−1
β = 102.811 (10)°	T = 297 K
V = 1567.1 (3) Å3	Cut block, pale brown
Z = 4	0.30 × 0.30 × 0.25 mm

Oxford Diffraction Gemini-S CCD-detector diffractometer	3061 independent reflections
Radiation source: Enhance (Mo) X-ray source	2203 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 26.0°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.950, Tmax = 0.980	k = −4→7
5928 measured reflections	l = −21→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0603P)2] where P = (Fo2 + 2Fc2)/3
3061 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O11A	0.46281 (7)	0.8636 (2)	0.32392 (7)	0.0479 (4)
N4A	0.09143 (8)	0.6731 (3)	0.07459 (9)	0.0423 (4)
C1A	0.33713 (9)	0.9649 (3)	0.17095 (8)	0.0376 (5)
C2A	0.32916 (10)	0.7560 (3)	0.13049 (10)	0.0468 (5)
C3A	0.24921 (10)	0.6600 (3)	0.09931 (10)	0.0458 (5)
C4A	0.17646 (9)	0.7749 (2)	0.10760 (8)	0.0343 (4)
C5A	0.18206 (9)	0.9815 (3)	0.14700 (9)	0.0423 (5)
C6A	0.26212 (10)	1.0747 (3)	0.17881 (10)	0.0435 (5)
C21A	0.49028 (10)	0.9216 (3)	0.25331 (10)	0.0541 (6)
C31A	0.42384 (9)	1.0756 (3)	0.20306 (10)	0.0493 (5)
O11	0.04161 (6)	−0.00501 (19)	−0.08313 (7)	0.0524 (4)
O12	0.10800 (7)	0.31952 (19)	−0.03468 (7)	0.0518 (4)
O31	0.42127 (8)	0.3454 (2)	0.01994 (9)	0.0690 (5)
O32	0.48427 (7)	0.1694 (2)	−0.06214 (8)	0.0596 (4)
O51	0.34790 (7)	−0.5258 (2)	−0.18874 (7)	0.0600 (4)
O52	0.21061 (8)	−0.5622 (2)	−0.20625 (7)	0.0544 (4)
N3	0.42210 (8)	0.2056 (2)	−0.03294 (8)	0.0456 (5)
N5	0.27785 (8)	−0.4606 (2)	−0.17929 (7)	0.0410 (4)
C1	0.19176 (8)	0.0264 (2)	−0.07694 (8)	0.0335 (4)
C2	0.26684 (9)	0.1488 (2)	−0.04825 (8)	0.0359 (5)
C3	0.34373 (9)	0.0683 (3)	−0.06244 (9)	0.0356 (4)
C4	0.34961 (9)	−0.1305 (2)	−0.10445 (9)	0.0369 (4)
C5	0.27433 (9)	−0.2501 (2)	−0.13187 (8)	0.0344 (4)
C6	0.19600 (9)	−0.1775 (2)	−0.11857 (8)	0.0349 (4)
C11	0.10697 (9)	0.1224 (3)	−0.06366 (9)	0.0376 (5)
H2A	0.37840	0.67910	0.12420	0.0560*
H3A	0.24490	0.51900	0.07300	0.0550*
H5A	0.13250	1.05830	0.15230	0.0510*
H6A	0.26570	1.21390	0.20610	0.0520*
H11A	0.4946 (13)	0.751 (4)	0.3511 (12)	0.077 (7)*
H21A	0.49730	0.78200	0.22460	0.0650*
H22A	0.54520	1.00100	0.26650	0.0650*
H31A	0.44640	1.13040	0.15900	0.0590*
H32A	0.41540	1.20950	0.23400	0.0590*
H41A	0.0919 (12)	0.580 (3)	0.0292 (12)	0.069 (6)*
H42A	0.0494 (13)	0.788 (3)	0.0611 (12)	0.069 (6)*
H43A	0.0745 (12)	0.566 (3)	0.1140 (12)	0.074 (6)*
H2	0.26560	0.28400	−0.01970	0.0430*
H4	0.40170	−0.18130	−0.11380	0.0440*
H6	0.14660	−0.26430	−0.13730	0.0420*

	U11	U22	U33	U12	U13	U23
O11A	0.0444 (6)	0.0510 (7)	0.0489 (7)	0.0053 (5)	0.0116 (5)	0.0101 (6)
N4A	0.0347 (7)	0.0486 (8)	0.0425 (8)	−0.0028 (6)	0.0065 (6)	−0.0058 (7)
C1A	0.0356 (8)	0.0449 (9)	0.0319 (8)	−0.0004 (7)	0.0067 (6)	0.0067 (7)
C2A	0.0335 (8)	0.0548 (10)	0.0541 (10)	0.0072 (7)	0.0141 (7)	−0.0055 (8)
C3A	0.0456 (9)	0.0435 (9)	0.0501 (10)	0.0029 (7)	0.0146 (8)	−0.0114 (8)
C4A	0.0328 (7)	0.0388 (8)	0.0308 (7)	−0.0001 (6)	0.0063 (6)	0.0004 (7)
C5A	0.0322 (8)	0.0431 (9)	0.0501 (10)	0.0093 (7)	0.0058 (7)	−0.0048 (8)
C6A	0.0443 (9)	0.0371 (8)	0.0469 (9)	0.0024 (7)	0.0057 (7)	−0.0059 (7)
C21A	0.0331 (8)	0.0813 (12)	0.0484 (10)	−0.0022 (8)	0.0100 (7)	0.0085 (9)
C31A	0.0380 (8)	0.0643 (11)	0.0455 (9)	−0.0075 (8)	0.0092 (7)	0.0108 (8)
O11	0.0340 (6)	0.0542 (7)	0.0722 (8)	−0.0052 (5)	0.0186 (6)	−0.0177 (6)
O12	0.0423 (6)	0.0502 (7)	0.0635 (8)	0.0051 (5)	0.0130 (5)	−0.0216 (6)
O31	0.0583 (8)	0.0695 (9)	0.0818 (10)	−0.0207 (6)	0.0211 (7)	−0.0324 (8)
O32	0.0366 (6)	0.0669 (8)	0.0808 (9)	−0.0044 (5)	0.0251 (6)	−0.0015 (7)
O51	0.0541 (7)	0.0592 (8)	0.0694 (8)	0.0179 (6)	0.0193 (6)	−0.0151 (6)
O52	0.0585 (7)	0.0490 (7)	0.0551 (8)	−0.0050 (6)	0.0111 (6)	−0.0155 (6)
N3	0.0385 (7)	0.0448 (8)	0.0540 (9)	−0.0055 (6)	0.0113 (6)	−0.0019 (7)
N5	0.0487 (8)	0.0381 (7)	0.0366 (7)	0.0082 (6)	0.0102 (6)	−0.0009 (6)
C1	0.0334 (7)	0.0366 (8)	0.0320 (7)	0.0018 (6)	0.0105 (6)	0.0014 (6)
C2	0.0399 (8)	0.0343 (8)	0.0353 (8)	0.0011 (6)	0.0124 (6)	−0.0031 (6)
C3	0.0325 (7)	0.0389 (8)	0.0361 (8)	−0.0015 (6)	0.0093 (6)	0.0010 (7)
C4	0.0341 (7)	0.0410 (8)	0.0381 (8)	0.0058 (6)	0.0136 (6)	0.0029 (7)
C5	0.0413 (8)	0.0335 (7)	0.0294 (7)	0.0056 (6)	0.0098 (6)	0.0004 (6)
C6	0.0338 (7)	0.0362 (8)	0.0343 (8)	−0.0013 (6)	0.0069 (6)	−0.0019 (7)
C11	0.0349 (8)	0.0430 (9)	0.0356 (8)	0.0020 (7)	0.0096 (6)	−0.0029 (7)

O11A—C21A	1.434 (2)	C5A—C6A	1.384 (2)
O11A—H11A	0.89 (2)	C21A—C31A	1.507 (2)
O11—C11	1.2606 (19)	C2A—H2A	0.9300
O12—C11	1.246 (2)	C3A—H3A	0.9300
O31—N3	1.2277 (19)	C5A—H5A	0.9300
O32—N3	1.2289 (18)	C6A—H6A	0.9300
O51—N5	1.2249 (17)	C21A—H21A	0.9700
O52—N5	1.2221 (18)	C21A—H22A	0.9700
N4A—C4A	1.474 (2)	C31A—H31A	0.9700
N4A—H43A	1.005 (19)	C31A—H32A	0.9700
N4A—H41A	0.958 (19)	C1—C2	1.3859 (19)
N4A—H42A	0.936 (19)	C1—C6	1.3939 (17)
N3—C3	1.474 (2)	C1—C11	1.527 (2)
N5—C5	1.4792 (17)	C2—C3	1.385 (2)
C1A—C6A	1.388 (2)	C3—C4	1.377 (2)
C1A—C2A	1.390 (2)	C4—C5	1.377 (2)
C1A—C31A	1.515 (2)	C5—C6	1.386 (2)
C2A—C3A	1.387 (2)	C2—H2	0.9300
C3A—C4A	1.373 (2)	C4—H4	0.9300
C4A—C5A	1.371 (2)	C6—H6	0.9300
C21A—O11A—H11A	112.3 (13)	C1A—C6A—H6A	119.00
C4A—N4A—H43A	110.1 (11)	C31A—C21A—H21A	110.00
H41A—N4A—H42A	109.2 (17)	O11A—C21A—H22A	110.00
H42A—N4A—H43A	108.8 (17)	O11A—C21A—H21A	110.00
C4A—N4A—H42A	111.1 (12)	C31A—C21A—H22A	110.00
H41A—N4A—H43A	105.6 (15)	H21A—C21A—H22A	108.00
C4A—N4A—H41A	111.8 (12)	H31A—C31A—H32A	107.00
O31—N3—O32	124.50 (14)	C1A—C31A—H31A	108.00
O32—N3—C3	117.66 (13)	C1A—C31A—H32A	108.00
O31—N3—C3	117.82 (13)	C21A—C31A—H31A	108.00
O51—N5—O52	123.36 (13)	C21A—C31A—H32A	108.00
O52—N5—C5	118.13 (12)	C2—C1—C6	118.82 (12)
O51—N5—C5	118.50 (12)	C2—C1—C11	118.94 (12)
C2A—C1A—C6A	117.62 (14)	C6—C1—C11	122.23 (12)
C6A—C1A—C31A	120.48 (15)	C1—C2—C3	119.55 (12)
C2A—C1A—C31A	121.87 (14)	N3—C3—C2	118.25 (14)
C1A—C2A—C3A	121.28 (15)	N3—C3—C4	118.85 (13)
C2A—C3A—C4A	119.40 (15)	C2—C3—C4	122.88 (14)
N4A—C4A—C3A	119.50 (13)	C3—C4—C5	116.54 (13)
N4A—C4A—C5A	119.71 (13)	N5—C5—C4	117.97 (12)
C3A—C4A—C5A	120.79 (14)	N5—C5—C6	119.34 (12)
C4A—C5A—C6A	119.46 (15)	C4—C5—C6	122.66 (12)
C1A—C6A—C5A	121.45 (16)	C1—C6—C5	119.53 (12)
O11A—C21A—C31A	109.07 (13)	O11—C11—O12	125.45 (14)
C1A—C31A—C21A	115.58 (14)	O11—C11—C1	117.05 (14)
C3A—C2A—H2A	119.00	O12—C11—C1	117.50 (13)
C1A—C2A—H2A	119.00	C1—C2—H2	120.00
C2A—C3A—H3A	120.00	C3—C2—H2	120.00
C4A—C3A—H3A	120.00	C3—C4—H4	122.00
C4A—C5A—H5A	120.00	C5—C4—H4	122.00
C6A—C5A—H5A	120.00	C1—C6—H6	120.00
C5A—C6A—H6A	119.00	C5—C6—H6	120.00
O32—N3—C3—C2	−161.49 (14)	C4A—C5A—C6A—C1A	0.8 (2)
O32—N3—C3—C4	16.9 (2)	O11A—C21A—C31A—C1A	−65.65 (18)
O31—N3—C3—C2	19.7 (2)	C6—C1—C2—C3	0.9 (2)
O31—N3—C3—C4	−161.93 (14)	C11—C1—C2—C3	−177.57 (13)
O51—N5—C5—C4	3.63 (19)	C2—C1—C6—C5	−1.49 (19)
O52—N5—C5—C6	1.02 (18)	C11—C1—C6—C5	176.97 (13)
O51—N5—C5—C6	−178.10 (12)	C2—C1—C11—O11	−172.71 (13)
O52—N5—C5—C4	−177.25 (13)	C2—C1—C11—O12	7.4 (2)
C6A—C1A—C2A—C3A	−0.2 (2)	C6—C1—C11—O11	8.8 (2)
C31A—C1A—C2A—C3A	−178.02 (15)	C6—C1—C11—O12	−171.08 (13)
C2A—C1A—C6A—C5A	−0.6 (2)	C1—C2—C3—N3	178.42 (13)
C31A—C1A—C6A—C5A	177.21 (15)	C1—C2—C3—C4	0.1 (2)
C2A—C1A—C31A—C21A	−51.8 (2)	N3—C3—C4—C5	−178.87 (13)
C6A—C1A—C31A—C21A	130.51 (16)	C2—C3—C4—C5	−0.6 (2)
C1A—C2A—C3A—C4A	0.9 (3)	C3—C4—C5—N5	178.18 (13)
C2A—C3A—C4A—C5A	−0.7 (2)	C3—C4—C5—C6	0.0 (2)
C2A—C3A—C4A—N4A	−179.93 (16)	N5—C5—C6—C1	−177.13 (12)
N4A—C4A—C5A—C6A	179.12 (14)	C4—C5—C6—C1	1.1 (2)
C3A—C4A—C5A—C6A	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O11A—H11A···O11i	0.89 (2)	1.88 (2)	2.7569 (16)	168 (2)
N4A—H41A···O12	0.958 (19)	1.924 (19)	2.845 (2)	160.8 (17)
N4A—H42A···O11ii	0.936 (19)	2.02 (2)	2.8905 (19)	154.0 (18)
N4A—H42A···O12ii	0.936 (19)	2.53 (2)	3.1033 (18)	119.9 (14)
N4A—H43A···O11Aiii	1.005 (19)	1.783 (19)	2.785 (2)	174.4 (19)
C5A—H5A···O11Aiv	0.93	2.43	3.317 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11A—H11A⋯O11i	0.89 (2)	1.88 (2)	2.7569 (16)	168 (2)
N4A—H41A⋯O12	0.958 (19)	1.924 (19)	2.845 (2)	160.8 (17)
N4A—H42A⋯O11ii	0.936 (19)	2.02 (2)	2.8905 (19)	154.0 (18)
N4A—H42A⋯O12ii	0.936 (19)	2.53 (2)	3.1033 (18)	119.9 (14)
N4A—H43A⋯O11Aiii	1.005 (19)	1.783 (19)	2.785 (2)	174.4 (19)
C5A—H5A⋯O11Aiv	0.93	2.43	3.317 (2)	161

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