4-(2-Hydroxy-ethyl)anilinium 3-carb-oxy-4-hydroxy-benzene-sulfonate monohydrate.

In the structure of the title compound, C(8)H(12)NO(+)·C(7)H(5)O(6)S(-)·H(2)O, isolated from the reaction of 2-(4-amino-phen-yl)ethanol with 5-sulfosalicylic acid, the cations form head-to-tail hydrogen-bonded chains through C(1) (1)(9) anilinium N(+)-H⋯O(hydrox-yl) inter-actions while the anions also form parallel but C(1) (1)(8)-linked chains through carboxylic acid O-H⋯O(sulfonate) inter-actions. These chains inter-associate through a number of N(+)-H⋯O and O-H⋯O bridging inter-actions, giving a two-dimensional array in the ab plane.

Related literature

For the structure of the 2-(4-amino­phen­yl)ethanol salt of 3,5-dinitro­benzoic acid, see: Smith & Wermuth (2009 ▶). For structures of 5-sulfosalicylic acid salts of aniline and substituted anilines, see: Bakasova et al. (1991 ▶); Smith (2005 ▶); Smith et al. (2005a ▶,b ▶, 2006 ▶). For hydrogen-bonding graph-set notation, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C8H12NO+·C7H5O6S−·H2O

M = 373.37

Triclinic,

a = 7.7412 (6) Å

b = 8.7977 (6) Å

c = 12.8330 (8) Å

α = 102.169 (6)°

β = 98.538 (6)°

γ = 101.366 (6)°

V = 820.97 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 200 K

0.40 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.934, T max = 0.980

10214 measured reflections

3215 independent reflections

2756 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.087

S = 0.99

3215 reflections

258 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.30 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 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049745/tk2580sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049745/tk2580Isup2.hkl

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

C8H12NO+·C7H5O6S−·H2O	Z = 2
Mr = 373.37	F(000) = 392
Triclinic, P1	Dx = 1.510 Mg m−3
Hall symbol: -P 1	Melting point: 498 K
a = 7.7412 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7977 (6) Å	Cell parameters from 4875 reflections
c = 12.8330 (8) Å	θ = 3.2–28.8°
α = 102.169 (6)°	µ = 0.24 mm−1
β = 98.538 (6)°	T = 200 K
γ = 101.366 (6)°	Plate, pale brown
V = 820.97 (11) Å3	0.40 × 0.40 × 0.20 mm

Oxford Diffraction Gemini-S CCD-detector diffractometer	3215 independent reflections
Radiation source: Enhance (Mo) X-ray source	2756 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.934, Tmax = 0.980	k = −10→10
10214 measured reflections	l = −15→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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.1198P] where P = (Fo2 + 2Fc2)/3
3215 reflections	(Δ/σ)max = 0.001
258 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.30 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	0.80608 (18)	0.87360 (14)	0.00089 (10)	0.0341 (4)
N4A	0.78541 (19)	0.07130 (16)	0.19112 (12)	0.0234 (4)
C1A	0.8163 (2)	0.53103 (17)	0.13072 (12)	0.0212 (4)
C2A	0.9359 (2)	0.51052 (18)	0.21625 (12)	0.0244 (4)
C3A	0.9278 (2)	0.35998 (18)	0.23691 (13)	0.0241 (5)
C4A	0.7995 (2)	0.23068 (17)	0.17042 (12)	0.0206 (4)
C5A	0.6827 (2)	0.24656 (19)	0.08278 (14)	0.0299 (5)
C6A	0.6921 (2)	0.39667 (19)	0.06356 (14)	0.0304 (5)
C11A	0.8410 (2)	0.72115 (19)	0.00469 (14)	0.0302 (5)
C21A	0.8142 (2)	0.69635 (18)	0.11528 (13)	0.0247 (4)
S5	0.31926 (5)	0.00829 (4)	0.26512 (3)	0.0203 (1)
O2	0.83804 (16)	0.60833 (15)	0.51275 (10)	0.0334 (4)
O11	0.43638 (16)	0.62380 (14)	0.25827 (10)	0.0310 (4)
O12	0.67893 (15)	0.76007 (13)	0.38590 (10)	0.0323 (4)
O51	0.17800 (14)	0.04515 (12)	0.19312 (9)	0.0253 (3)
O52	0.25277 (15)	−0.07135 (13)	0.34506 (9)	0.0289 (4)
O53	0.43041 (14)	−0.08330 (13)	0.20599 (9)	0.0292 (3)
C1	0.5791 (2)	0.47935 (17)	0.36674 (12)	0.0205 (4)
C2	0.7134 (2)	0.47689 (18)	0.45347 (12)	0.0226 (4)
C3	0.7206 (2)	0.33328 (19)	0.48234 (13)	0.0257 (5)
C4	0.5988 (2)	0.19310 (18)	0.42610 (12)	0.0227 (5)
C5	0.46674 (19)	0.19342 (17)	0.33820 (12)	0.0192 (4)
C6	0.45641 (19)	0.33538 (17)	0.30967 (12)	0.0201 (4)
C11	0.5704 (2)	0.63262 (18)	0.33854 (13)	0.0233 (5)
O1W	0.9577 (2)	0.04283 (16)	0.39011 (11)	0.0352 (4)
H2A	1.02240	0.59840	0.26020	0.0290*
H3A	1.00740	0.34710	0.29440	0.0290*
H5A	0.59910	0.15770	0.03750	0.0360*
H6A	0.61400	0.40810	0.00480	0.0370*
H11A	0.824 (3)	0.894 (3)	−0.0554 (19)	0.047 (6)*
H12A	0.75870	0.63730	−0.05290	0.0360*
H13A	0.96310	0.71970	−0.00400	0.0360*
H21A	0.90780	0.77360	0.17060	0.0300*
H22A	0.70000	0.71900	0.12720	0.0300*
H41A	0.858 (3)	0.075 (2)	0.2578 (17)	0.040 (5)*
H42A	0.818 (3)	0.009 (3)	0.1367 (19)	0.049 (6)*
H43A	0.668 (3)	0.026 (2)	0.1963 (15)	0.035 (5)*
H2	0.823 (3)	0.685 (3)	0.491 (2)	0.062 (8)*
H3	0.80840	0.33250	0.54000	0.0310*
H4	0.60390	0.09830	0.44620	0.0270*
H6	0.36750	0.33520	0.25230	0.0240*
H11	0.434 (3)	0.715 (3)	0.2491 (17)	0.047 (6)*
H11W	0.883 (4)	−0.035 (3)	0.403 (2)	0.069 (8)*
H12W	1.047 (3)	0.002 (3)	0.3819 (17)	0.046 (6)*

	U11	U22	U33	U12	U13	U23
O11A	0.0568 (8)	0.0265 (6)	0.0266 (7)	0.0153 (6)	0.0133 (6)	0.0147 (5)
N4A	0.0250 (7)	0.0188 (7)	0.0293 (8)	0.0067 (6)	0.0076 (6)	0.0093 (6)
C1A	0.0239 (8)	0.0180 (7)	0.0226 (8)	0.0051 (6)	0.0050 (6)	0.0066 (6)
C2A	0.0268 (8)	0.0188 (7)	0.0228 (8)	−0.0002 (6)	0.0006 (6)	0.0028 (6)
C3A	0.0250 (8)	0.0252 (8)	0.0217 (8)	0.0058 (6)	0.0000 (6)	0.0085 (6)
C4A	0.0227 (8)	0.0164 (7)	0.0257 (8)	0.0067 (6)	0.0079 (6)	0.0076 (6)
C5A	0.0284 (9)	0.0190 (8)	0.0356 (9)	0.0014 (7)	−0.0066 (7)	0.0054 (7)
C6A	0.0290 (9)	0.0230 (8)	0.0341 (9)	0.0041 (7)	−0.0094 (7)	0.0087 (7)
C11A	0.0428 (10)	0.0227 (8)	0.0291 (9)	0.0100 (7)	0.0133 (8)	0.0088 (7)
C21A	0.0302 (8)	0.0182 (7)	0.0250 (8)	0.0045 (6)	0.0040 (7)	0.0062 (6)
S5	0.0188 (2)	0.0172 (2)	0.0251 (2)	0.0033 (1)	0.0016 (2)	0.0087 (2)
O2	0.0322 (7)	0.0256 (6)	0.0333 (7)	−0.0010 (5)	−0.0059 (5)	0.0035 (5)
O11	0.0337 (7)	0.0180 (6)	0.0393 (7)	0.0060 (5)	−0.0028 (5)	0.0102 (5)
O12	0.0320 (6)	0.0204 (6)	0.0399 (7)	0.0000 (5)	0.0026 (5)	0.0062 (5)
O51	0.0224 (6)	0.0253 (6)	0.0276 (6)	0.0033 (5)	−0.0010 (5)	0.0114 (5)
O52	0.0258 (6)	0.0283 (6)	0.0352 (7)	0.0027 (5)	0.0032 (5)	0.0191 (5)
O53	0.0270 (6)	0.0211 (5)	0.0377 (7)	0.0061 (5)	0.0065 (5)	0.0032 (5)
C1	0.0206 (7)	0.0209 (7)	0.0212 (7)	0.0058 (6)	0.0071 (6)	0.0049 (6)
C2	0.0216 (7)	0.0229 (8)	0.0211 (8)	0.0031 (6)	0.0050 (6)	0.0023 (6)
C3	0.0232 (8)	0.0311 (8)	0.0225 (8)	0.0070 (7)	0.0000 (6)	0.0085 (7)
C4	0.0248 (8)	0.0234 (8)	0.0236 (8)	0.0085 (6)	0.0053 (6)	0.0106 (6)
C5	0.0179 (7)	0.0193 (7)	0.0211 (7)	0.0044 (6)	0.0053 (6)	0.0055 (6)
C6	0.0196 (7)	0.0205 (7)	0.0211 (7)	0.0064 (6)	0.0027 (6)	0.0066 (6)
C11	0.0236 (8)	0.0199 (8)	0.0271 (8)	0.0056 (6)	0.0075 (7)	0.0054 (6)
O1W	0.0372 (8)	0.0354 (7)	0.0397 (7)	0.0111 (6)	0.0129 (6)	0.0178 (6)

S5—O51	1.4563 (12)	C4A—C5A	1.384 (2)
S5—O52	1.4581 (12)	C5A—C6A	1.384 (2)
S5—O53	1.4747 (12)	C11A—C21A	1.518 (2)
S5—C5	1.7723 (16)	C2A—H2A	0.9300
O11A—C11A	1.429 (2)	C3A—H3A	0.9300
O11A—H11A	0.81 (2)	C5A—H5A	0.9300
O2—C2	1.348 (2)	C6A—H6A	0.9300
O11—C11	1.327 (2)	C11A—H12A	0.9700
O12—C11	1.234 (2)	C11A—H13A	0.9700
O2—H2	0.80 (3)	C21A—H21A	0.9700
O11—H11	0.84 (3)	C21A—H22A	0.9700
O1W—H11W	0.87 (3)	C1—C2	1.413 (2)
O1W—H12W	0.85 (2)	C1—C11	1.479 (2)
N4A—C4A	1.468 (2)	C1—C6	1.404 (2)
N4A—H41A	0.94 (2)	C2—C3	1.398 (2)
N4A—H42A	0.89 (2)	C3—C4	1.377 (2)
N4A—H43A	0.94 (2)	C4—C5	1.406 (2)
C1A—C6A	1.393 (2)	C5—C6	1.387 (2)
C1A—C2A	1.394 (2)	C3—H3	0.9300
C1A—C21A	1.512 (2)	C4—H4	0.9300
C2A—C3A	1.396 (2)	C6—H6	0.9300
C3A—C4A	1.379 (2)
O51—S5—O53	113.02 (7)	C5A—C6A—H6A	119.00
O51—S5—C5	106.82 (7)	C1A—C6A—H6A	119.00
O52—S5—O53	110.32 (7)	C21A—C11A—H12A	110.00
O52—S5—C5	107.10 (7)	C21A—C11A—H13A	110.00
O53—S5—C5	105.72 (7)	H12A—C11A—H13A	109.00
O51—S5—O52	113.33 (7)	O11A—C11A—H12A	110.00
C11A—O11A—H11A	109.8 (18)	O11A—C11A—H13A	110.00
C2—O2—H2	109.8 (18)	C1A—C21A—H22A	108.00
C11—O11—H11	110.7 (16)	C1A—C21A—H21A	108.00
H11W—O1W—H12W	102 (3)	H21A—C21A—H22A	107.00
H41A—N4A—H43A	105.5 (18)	C11A—C21A—H21A	108.00
H41A—N4A—H42A	110 (2)	C11A—C21A—H22A	108.00
C4A—N4A—H41A	112.1 (11)	C2—C1—C11	119.52 (14)
C4A—N4A—H43A	111.1 (12)	C6—C1—C11	121.67 (14)
H42A—N4A—H43A	110 (2)	C2—C1—C6	118.82 (14)
C4A—N4A—H42A	108.5 (17)	O2—C2—C3	116.62 (14)
C2A—C1A—C6A	118.47 (14)	C1—C2—C3	120.02 (14)
C2A—C1A—C21A	120.69 (14)	O2—C2—C1	123.35 (14)
C6A—C1A—C21A	120.74 (14)	C2—C3—C4	120.56 (15)
C1A—C2A—C3A	120.99 (14)	C3—C4—C5	119.94 (15)
C2A—C3A—C4A	118.74 (14)	C4—C5—C6	120.10 (14)
N4A—C4A—C5A	118.38 (14)	S5—C5—C4	118.07 (12)
C3A—C4A—C5A	121.53 (15)	S5—C5—C6	121.82 (12)
N4A—C4A—C3A	120.08 (14)	C1—C6—C5	120.53 (14)
C4A—C5A—C6A	119.01 (15)	O11—C11—O12	121.98 (15)
C1A—C6A—C5A	121.20 (15)	O11—C11—C1	115.13 (14)
O11A—C11A—C21A	106.35 (13)	O12—C11—C1	122.89 (14)
C1A—C21A—C11A	115.37 (13)	C4—C3—H3	120.00
C1A—C2A—H2A	120.00	C2—C3—H3	120.00
C3A—C2A—H2A	119.00	C3—C4—H4	120.00
C4A—C3A—H3A	121.00	C5—C4—H4	120.00
C2A—C3A—H3A	121.00	C1—C6—H6	120.00
C4A—C5A—H5A	121.00	C5—C6—H6	120.00
C6A—C5A—H5A	120.00
O52—S5—C5—C4	48.08 (14)	O11A—C11A—C21A—C1A	170.97 (13)
O52—S5—C5—C6	−133.01 (13)	C6—C1—C2—O2	179.56 (14)
O53—S5—C5—C4	−69.56 (13)	C6—C1—C2—C3	−1.1 (2)
O53—S5—C5—C6	109.35 (13)	C11—C1—C2—O2	−0.7 (2)
O51—S5—C5—C6	−11.28 (15)	C11—C1—C2—C3	178.66 (14)
O51—S5—C5—C4	169.81 (12)	C2—C1—C6—C5	0.2 (2)
C6A—C1A—C21A—C11A	−59.7 (2)	C11—C1—C6—C5	−179.57 (14)
C2A—C1A—C21A—C11A	123.94 (16)	C2—C1—C11—O11	−177.96 (14)
C6A—C1A—C2A—C3A	−2.3 (2)	C2—C1—C11—O12	1.9 (2)
C21A—C1A—C2A—C3A	174.16 (15)	C6—C1—C11—O11	1.8 (2)
C2A—C1A—C6A—C5A	2.1 (2)	C6—C1—C11—O12	−178.40 (15)
C21A—C1A—C6A—C5A	−174.34 (15)	O2—C2—C3—C4	−179.87 (14)
C1A—C2A—C3A—C4A	0.5 (2)	C1—C2—C3—C4	0.7 (2)
C2A—C3A—C4A—C5A	1.6 (2)	C2—C3—C4—C5	0.6 (2)
C2A—C3A—C4A—N4A	−178.94 (14)	C3—C4—C5—S5	177.44 (12)
N4A—C4A—C5A—C6A	178.74 (15)	C3—C4—C5—C6	−1.5 (2)
C3A—C4A—C5A—C6A	−1.8 (2)	S5—C5—C6—C1	−177.77 (12)
C4A—C5A—C6A—C1A	−0.1 (2)	C4—C5—C6—C1	1.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O12	0.80 (3)	1.93 (3)	2.6302 (18)	145 (2)
O11—H11···O53i	0.84 (3)	1.97 (3)	2.8034 (17)	172 (2)
O11A—H11A···O51ii	0.81 (2)	1.95 (2)	2.7444 (17)	169 (2)
N4A—H41A···O1W	0.94 (2)	1.86 (2)	2.784 (2)	166.5 (19)
N4A—H42A···O11Aiii	0.89 (2)	1.87 (2)	2.7287 (19)	161 (2)
N4A—H43A···O53	0.94 (2)	1.94 (2)	2.8689 (19)	175.6 (18)
O1W—H11W···O12iii	0.87 (3)	2.10 (3)	2.9396 (19)	164 (2)
O1W—H12W···O52iv	0.85 (2)	1.92 (2)	2.759 (2)	171 (2)
C3A—H3A···O2v	0.93	2.50	3.373 (2)	157
C6—H6···O51	0.93	2.57	2.9437 (19)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O12	0.80 (3)	1.93 (3)	2.6302 (18)	145 (2)
O11—H11⋯O53i	0.84 (3)	1.97 (3)	2.8034 (17)	172 (2)
O11A—H11A⋯O51ii	0.81 (2)	1.95 (2)	2.7444 (17)	169 (2)
N4A—H41A⋯O1W	0.94 (2)	1.86 (2)	2.784 (2)	166.5 (19)
N4A—H42A⋯O11A iii	0.89 (2)	1.87 (2)	2.7287 (19)	161 (2)
N4A—H43A⋯O53	0.94 (2)	1.94 (2)	2.8689 (19)	175.6 (18)
O1W—H11W⋯O12iii	0.87 (3)	2.10 (3)	2.9396 (19)	164 (2)
O1W—H12W⋯O52iv	0.85 (2)	1.92 (2)	2.759 (2)	171 (2)

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