8-Ammonio-naphthalene-2-sulfonate monohydrate: the zwitterionic hydrate of 1,7-Cleve's acid.

The structure of 8-amino-2-naphthalene-sulfonic acid monohydrate (1,7-Cleve's acid hydrate), C(10)H(9)NO(3)S·H(2)O, shows the presence of a sulfonate-aminium group zwitterion, both groups and the water mol-ecule of solvation giving cyclic R(3) (3)(8) O-H⋯O and N-H⋯O inter-molecular hydrogen-bonding inter-actions, forming chains which extend down the a axis of the unit cell. Additional peripheral associations, including weak aromatic ring π-π inter-actions [centroid-centroid distance = 3.6299 (15) Å], result in a two-dimensional sheet structure.

Related literature

1,7-Cleve’s acid and 1,6-Cleve’s acid have important industrialchemical applications as azo dye precursors, see: O’Neil (2001 ▶). For the preliminary crystal data for a number of aminona­phthalenesulfonic acids, see: Corbridge et al. (1966 ▶). For the strutures of 5-amino-2-naphthalene­sulfonic acid (1,6-Cleve’s acid) and the 1:1 adduct of 1,7-Cleve’s acid with strychnine, see: Smith et al. (2004 ▶, 2007 ▶).

Experimental

Crystal data

C10H9NO3S·H2O

M = 241.27

Orthorhombic,

a = 7.1616 (3) Å

b = 16.4608 (7) Å

c = 8.9059 (3) Å

V = 1049.88 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 297 K

0.35 × 0.20 × 0.05 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.950, T max = 0.990

5904 measured reflections

2252 independent reflections

1830 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.076

S = 0.91

2252 reflections

165 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 974 Friedel pairs

Flack parameter: 0.06 (8)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; 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 I, global. DOI: 10.1107/S1600536809030396/tk2500sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030396/tk2500Isup2.hkl

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

C10H9NO3S·H2O	F(000) = 504
Mr = 241.27	Dx = 1.526 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2826 reflections
a = 7.1616 (3) Å	θ = 3.1–32.3°
b = 16.4608 (7) Å	µ = 0.31 mm−1
c = 8.9059 (3) Å	T = 297 K
V = 1049.88 (7) Å3	Flat prism, colourless
Z = 4	0.35 × 0.20 × 0.05 mm

Oxford Diffraction Gemini-S CCD-detector diffractometer	2252 independent reflections
Radiation source: Enhance (Mo) X-ray tube	1830 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.950, Tmax = 0.990	k = −21→21
5904 measured reflections	l = −11→11

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max = 0.003
2252 reflections	Δρmax = 0.29 e Å−3
165 parameters	Δρmin = −0.17 e Å−3
1 restraint	Absolute structure: Flack (1983), 974 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (8)

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
S2	0.91078 (7)	0.91246 (3)	0.30596 (6)	0.0279 (2)
O21	0.9227 (3)	0.98981 (10)	0.38255 (19)	0.0426 (6)
O22	1.0718 (2)	0.89287 (11)	0.21446 (19)	0.0432 (6)
O23	0.7375 (3)	0.90447 (11)	0.21899 (17)	0.0386 (6)
N8	0.7911 (4)	0.89568 (12)	0.9061 (2)	0.0316 (7)
C1	0.8622 (3)	0.85751 (14)	0.5919 (3)	0.0244 (6)
C2	0.8963 (3)	0.83679 (13)	0.4461 (2)	0.0247 (6)
C3	0.9158 (4)	0.75485 (14)	0.4020 (3)	0.0313 (7)
C4	0.8930 (4)	0.69545 (14)	0.5046 (3)	0.0328 (7)
C5	0.8196 (4)	0.65100 (14)	0.7627 (3)	0.0350 (7)
C6	0.7800 (4)	0.66940 (15)	0.9072 (3)	0.0377 (8)
C7	0.7701 (4)	0.75056 (16)	0.9537 (2)	0.0344 (8)
C8	0.8000 (3)	0.81129 (15)	0.8546 (2)	0.0266 (7)
C9	0.8386 (3)	0.79617 (14)	0.7015 (2)	0.0244 (6)
C10	0.8515 (3)	0.71317 (14)	0.6564 (3)	0.0270 (7)
O1W	0.6039 (4)	1.01561 (13)	0.7583 (3)	0.0636 (9)
H1	0.85450	0.91190	0.61930	0.0290*
H3	0.94410	0.74190	0.30290	0.0380*
H4	0.90490	0.64150	0.47490	0.0390*
H5	0.82590	0.59690	0.73300	0.0420*
H6	0.75920	0.62790	0.97610	0.0450*
H7	0.74290	0.76270	1.05330	0.0410*
H81	0.762 (4)	0.8959 (14)	1.002 (3)	0.038 (6)*
H82	0.904 (5)	0.9182 (18)	0.897 (4)	0.051 (9)*
H83	0.690 (7)	0.927 (3)	0.860 (4)	0.056 (10)*
H11W	0.502 (6)	1.0367 (18)	0.746 (4)	0.076 (10)*
H12W	0.699 (4)	1.0497 (17)	0.738 (3)	0.082 (8)*

	U11	U22	U33	U12	U13	U23
S2	0.0338 (3)	0.0303 (3)	0.0196 (2)	−0.0020 (2)	0.0031 (3)	0.0018 (2)
O21	0.0683 (14)	0.0271 (8)	0.0325 (9)	−0.0069 (9)	0.0053 (10)	0.0014 (7)
O22	0.0422 (11)	0.0546 (11)	0.0327 (9)	−0.0010 (9)	0.0135 (9)	0.0033 (8)
O23	0.0390 (10)	0.0510 (11)	0.0258 (8)	0.0022 (9)	−0.0032 (8)	0.0010 (7)
N8	0.0405 (14)	0.0348 (12)	0.0195 (10)	−0.0027 (10)	0.0037 (10)	−0.0013 (8)
C1	0.0254 (12)	0.0231 (10)	0.0247 (10)	0.0015 (9)	−0.0001 (9)	−0.0007 (8)
C2	0.0233 (11)	0.0272 (10)	0.0236 (10)	−0.0016 (10)	0.0026 (9)	0.0027 (8)
C3	0.0366 (13)	0.0313 (11)	0.0260 (10)	0.0014 (11)	0.0054 (11)	−0.0064 (9)
C4	0.0370 (13)	0.0266 (11)	0.0347 (12)	0.0026 (11)	0.0025 (12)	−0.0049 (9)
C5	0.0330 (12)	0.0277 (12)	0.0442 (14)	0.0006 (11)	0.0001 (11)	0.0054 (11)
C6	0.0385 (15)	0.0351 (13)	0.0395 (14)	0.0001 (12)	0.0002 (13)	0.0163 (12)
C7	0.0338 (14)	0.0455 (14)	0.0239 (11)	−0.0030 (12)	0.0025 (11)	0.0048 (11)
C8	0.0230 (12)	0.0308 (12)	0.0259 (11)	−0.0014 (10)	−0.0005 (9)	0.0002 (9)
C9	0.0211 (11)	0.0263 (11)	0.0259 (10)	0.0000 (9)	−0.0009 (9)	−0.0002 (9)
C10	0.0217 (12)	0.0270 (12)	0.0323 (11)	0.0002 (10)	0.0005 (10)	0.0019 (10)
O1W	0.0410 (12)	0.0407 (12)	0.109 (2)	0.0022 (11)	−0.0058 (14)	0.0170 (12)

S2—O21	1.4470 (17)	C4—C10	1.415 (4)
S2—O22	1.4484 (16)	C5—C10	1.413 (4)
S2—O23	1.469 (2)	C5—C6	1.352 (4)
S2—C2	1.766 (2)	C6—C7	1.401 (4)
O1W—H12W	0.90 (3)	C7—C8	1.351 (3)
O1W—H11W	0.82 (4)	C8—C9	1.413 (3)
N8—C8	1.464 (3)	C9—C10	1.427 (3)
N8—H81	0.88 (3)	C1—H1	0.9300
N8—H82	0.89 (4)	C3—H3	0.9300
N8—H83	0.98 (4)	C4—H4	0.9300
C1—C2	1.365 (3)	C5—H5	0.9300
C1—C9	1.415 (3)	C6—H6	0.9300
C2—C3	1.412 (3)	C7—H7	0.9300
C3—C4	1.348 (4)
O21—S2—O22	114.47 (11)	N8—C8—C9	118.54 (19)
O21—S2—O23	112.16 (11)	C7—C8—C9	122.1 (2)
O21—S2—C2	106.91 (10)	N8—C8—C7	119.38 (18)
O22—S2—O23	110.86 (10)	C1—C9—C10	118.78 (19)
O22—S2—C2	106.70 (10)	C8—C9—C10	116.9 (2)
O23—S2—C2	105.06 (10)	C1—C9—C8	124.3 (2)
H11W—O1W—H12W	113 (3)	C5—C10—C9	119.6 (2)
H81—N8—H83	103 (3)	C4—C10—C9	118.7 (2)
H82—N8—H83	114 (2)	C4—C10—C5	121.7 (2)
C8—N8—H81	108.6 (15)	C2—C1—H1	120.00
C8—N8—H82	109 (2)	C9—C1—H1	120.00
H81—N8—H82	108 (3)	C4—C3—H3	120.00
C8—N8—H83	111 (3)	C2—C3—H3	120.00
C2—C1—C9	120.0 (2)	C3—C4—H4	119.00
S2—C2—C3	118.12 (16)	C10—C4—H4	119.00
S2—C2—C1	120.44 (17)	C10—C5—H5	120.00
C1—C2—C3	121.4 (2)	C6—C5—H5	120.00
C2—C3—C4	119.5 (2)	C5—C6—H6	120.00
C3—C4—C10	121.6 (2)	C7—C6—H6	120.00
C6—C5—C10	120.6 (2)	C6—C7—H7	120.00
C5—C6—C7	120.4 (2)	C8—C7—H7	120.00
C6—C7—C8	120.3 (2)
O21—S2—C2—C1	12.5 (2)	C10—C5—C6—C7	0.0 (4)
O21—S2—C2—C3	−169.2 (2)	C6—C5—C10—C4	−180.0 (3)
O22—S2—C2—C1	135.40 (18)	C6—C5—C10—C9	−1.1 (4)
O22—S2—C2—C3	−46.3 (2)	C5—C6—C7—C8	0.0 (4)
O23—S2—C2—C1	−106.85 (19)	C6—C7—C8—N8	−179.3 (2)
O23—S2—C2—C3	71.4 (2)	C6—C7—C8—C9	1.2 (4)
C9—C1—C2—S2	175.82 (16)	N8—C8—C9—C1	−2.7 (3)
C9—C1—C2—C3	−2.4 (3)	N8—C8—C9—C10	178.2 (2)
C2—C1—C9—C8	−179.0 (2)	C7—C8—C9—C1	176.9 (2)
C2—C1—C9—C10	0.1 (3)	C7—C8—C9—C10	−2.2 (3)
S2—C2—C3—C4	−175.6 (2)	C1—C9—C10—C4	1.9 (3)
C1—C2—C3—C4	2.7 (4)	C1—C9—C10—C5	−177.0 (2)
C2—C3—C4—C10	−0.6 (4)	C8—C9—C10—C4	−179.0 (2)
C3—C4—C10—C5	177.2 (3)	C8—C9—C10—C5	2.1 (3)
C3—C4—C10—C9	−1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O23i	0.82 (4)	1.98 (4)	2.798 (3)	176 (3)
O1W—H12W···O22ii	0.90 (3)	1.91 (3)	2.796 (3)	169 (3)
N8—H81···O23iii	0.88 (3)	1.95 (3)	2.817 (2)	171 (2)
N8—H82···O21ii	0.89 (4)	1.96 (3)	2.793 (3)	154 (3)
N8—H83···O1W	0.98 (4)	1.82 (4)	2.725 (3)	152 (4)
C1—H1···O21	0.93	2.52	2.899 (3)	105
C1—H1···N8	0.93	2.61	2.913 (3)	100
C6—H6···O22iv	0.93	2.53	3.281 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11W⋯O23i	0.82 (4)	1.98 (4)	2.798 (3)	176 (3)
O1W—H12W⋯O22ii	0.90 (3)	1.91 (3)	2.796 (3)	169 (3)
N8—H81⋯O23iii	0.88 (3)	1.95 (3)	2.817 (2)	171 (2)
N8—H82⋯O21ii	0.89 (4)	1.96 (3)	2.793 (3)	154 (3)
N8—H83⋯O1W	0.98 (4)	1.82 (4)	2.725 (3)	152 (4)

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