1-Ammonio-naphthalene-2-sulfonate.

In the mol-ecule of the zwitterionic title compound, C(10)H(9)NO(3)S, an intra-molecular N-H⋯O hydrogen bond results in the formation of an almost planar six-membered ring (r.m.s daviation = 0.0150 Å), which is oriented at a dihedral angle of 1.63 (3)° with respect to the naphthalene ring system. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network.

Related literature

For general background to the use of amino naphthalene sulfonic acid derivatives as a inter­mediates for the syntheses of azo dyes, see: O’Neil (2001 ▶). For related structures, see: Arshad et al. (2008a ▶,b ▶); Genther et al. (2007 ▶); Shafiq et al. (2008 ▶); Smith et al. (2004 ▶, 2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H9NO3S

M = 223.24

Orthorhombic,

a = 9.4337 (3) Å

b = 10.6359 (4) Å

c = 18.6775 (6) Å

V = 1874.02 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.29 × 0.21 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.911, T max = 0.943

10742 measured reflections

2326 independent reflections

1763 reflections with I > 2/s(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.03

2326 reflections

145 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809036538/hk2764sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036538/hk2764Isup2.hkl

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

C10H9NO3S	F(000) = 928
Mr = 223.24	Dx = 1.582 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2779 reflections
a = 9.4337 (3) Å	θ = 3.1–27.5°
b = 10.6359 (4) Å	µ = 0.33 mm−1
c = 18.6775 (6) Å	T = 296 K
V = 1874.02 (11) Å3	Hexagonal, dark brown
Z = 8	0.29 × 0.21 × 0.18 mm

Bruker Kappa APEXII CCD area-detector diffractometer	2326 independent reflections
Radiation source: fine-focus sealed tube	1763 reflections with I > 2/s(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.911, Tmax = 0.943	k = −14→8
10742 measured reflections	l = −24→24

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.6846P] where P = (Fo2 + 2Fc2)/3
2326 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.50 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
S1	0.48056 (5)	0.72906 (4)	1.02833 (2)	0.02659 (15)
O1	0.62861 (15)	0.69891 (13)	1.04059 (8)	0.0375 (4)
O2	0.38420 (16)	0.65642 (14)	1.07238 (7)	0.0401 (4)
O3	0.45788 (15)	0.86350 (13)	1.03188 (7)	0.0369 (3)
N1	0.25407 (18)	0.53879 (16)	0.96588 (9)	0.0282 (3)
H1N	0.270 (2)	0.459 (2)	0.9642 (10)	0.034*
H2N	0.273 (2)	0.565 (2)	1.0112 (12)	0.034*
H3N	0.166 (3)	0.558 (2)	0.9579 (11)	0.034*
C1	0.34654 (18)	0.60250 (16)	0.91466 (9)	0.0248 (4)
C2	0.44755 (18)	0.68602 (17)	0.93750 (9)	0.0253 (4)
C3	0.5354 (2)	0.7463 (2)	0.88661 (11)	0.0346 (4)
H3	0.6054	0.8017	0.9018	0.041*
C4	0.5178 (2)	0.7236 (2)	0.81550 (11)	0.0373 (5)
H4	0.5756	0.7646	0.7826	0.045*
C5	0.3947 (2)	0.6159 (2)	0.71689 (11)	0.0411 (5)
H5	0.4495	0.6590	0.6836	0.049*
C6	0.2971 (3)	0.5317 (2)	0.69409 (12)	0.0455 (6)
H6	0.2852	0.5175	0.6453	0.055*
C7	0.2144 (3)	0.4659 (2)	0.74345 (12)	0.0457 (5)
H7	0.1486	0.4074	0.7272	0.055*
C8	0.2287 (2)	0.48638 (19)	0.81515 (11)	0.0373 (5)
H8	0.1727	0.4418	0.8473	0.045*
C9	0.32805 (19)	0.57488 (17)	0.84084 (10)	0.0277 (4)
C10	0.4142 (2)	0.63928 (18)	0.79073 (10)	0.0317 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0286 (2)	0.0233 (2)	0.0278 (2)	−0.00027 (18)	−0.00188 (17)	0.00027 (17)
O1	0.0327 (7)	0.0331 (7)	0.0467 (8)	0.0037 (6)	−0.0106 (6)	−0.0016 (6)
O2	0.0467 (9)	0.0439 (8)	0.0297 (7)	−0.0125 (7)	0.0029 (6)	0.0025 (6)
O3	0.0451 (8)	0.0254 (7)	0.0402 (8)	0.0056 (6)	−0.0033 (6)	−0.0043 (6)
N1	0.0271 (8)	0.0231 (8)	0.0343 (9)	−0.0033 (7)	0.0033 (7)	0.0014 (7)
C1	0.0224 (8)	0.0216 (8)	0.0303 (9)	0.0027 (7)	0.0034 (7)	0.0015 (7)
C2	0.0252 (8)	0.0231 (8)	0.0277 (9)	0.0012 (7)	0.0008 (7)	0.0000 (7)
C3	0.0301 (9)	0.0379 (11)	0.0357 (10)	−0.0108 (8)	0.0024 (8)	0.0019 (8)
C4	0.0364 (10)	0.0415 (12)	0.0339 (10)	−0.0053 (9)	0.0087 (8)	0.0057 (9)
C5	0.0490 (12)	0.0454 (12)	0.0290 (10)	0.0119 (11)	0.0036 (9)	0.0006 (9)
C6	0.0558 (13)	0.0454 (13)	0.0353 (11)	0.0151 (11)	−0.0103 (10)	−0.0111 (9)
C7	0.0502 (13)	0.0377 (12)	0.0493 (13)	0.0010 (10)	−0.0143 (10)	−0.0119 (10)
C8	0.0360 (11)	0.0323 (10)	0.0435 (11)	−0.0026 (9)	−0.0048 (8)	−0.0044 (9)
C9	0.0259 (8)	0.0244 (9)	0.0328 (10)	0.0051 (7)	−0.0016 (7)	−0.0023 (7)
C10	0.0322 (9)	0.0323 (10)	0.0305 (10)	0.0055 (8)	0.0005 (7)	0.0004 (8)

S1—O3	1.4473 (14)	C4—C10	1.405 (3)
S1—O2	1.4491 (14)	C4—H4	0.9300
S1—O1	1.4513 (14)	C5—C6	1.353 (3)
S1—C2	1.7845 (18)	C5—C10	1.413 (3)
N1—C1	1.461 (2)	C5—H5	0.9300
N1—H1N	0.86 (2)	C6—C7	1.395 (3)
N1—H2N	0.91 (2)	C6—H6	0.9300
N1—H3N	0.86 (2)	C7—C8	1.363 (3)
C1—C2	1.371 (2)	C7—H7	0.9300
C1—C9	1.420 (2)	C8—C9	1.412 (3)
C2—C3	1.415 (3)	C8—H8	0.9300
C3—C4	1.360 (3)	C9—C10	1.416 (3)
C3—H3	0.9300
O3—S1—O2	114.07 (9)	C3—C4—C10	121.32 (18)
O3—S1—O1	110.69 (9)	C3—C4—H4	119.3
O2—S1—O1	113.34 (9)	C10—C4—H4	119.3
O3—S1—C2	105.74 (8)	C6—C5—C10	120.8 (2)
O2—S1—C2	107.07 (8)	C6—C5—H5	119.6
O1—S1—C2	105.15 (8)	C10—C5—H5	119.6
C1—N1—H1N	109.3 (14)	C5—C6—C7	120.3 (2)
C1—N1—H2N	110.2 (14)	C5—C6—H6	119.9
H1N—N1—H2N	107.7 (19)	C7—C6—H6	119.9
C1—N1—H3N	110.5 (14)	C8—C7—C6	120.9 (2)
H1N—N1—H3N	113 (2)	C8—C7—H7	119.5
H2N—N1—H3N	106.3 (19)	C6—C7—H7	119.5
C2—C1—C9	121.43 (16)	C7—C8—C9	120.4 (2)
C2—C1—N1	120.77 (16)	C7—C8—H8	119.8
C9—C1—N1	117.79 (16)	C9—C8—H8	119.8
C1—C2—C3	119.45 (17)	C8—C9—C10	118.59 (17)
C1—C2—S1	125.70 (14)	C8—C9—C1	123.31 (18)
C3—C2—S1	114.85 (14)	C10—C9—C1	118.10 (16)
C4—C3—C2	120.28 (18)	C4—C10—C5	121.61 (19)
C4—C3—H3	119.9	C4—C10—C9	119.36 (17)
C2—C3—H3	119.9	C5—C10—C9	119.03 (19)
C9—C1—C2—C3	0.1 (3)	C6—C7—C8—C9	0.0 (3)
N1—C1—C2—C3	−179.95 (17)	C7—C8—C9—C10	−1.4 (3)
C9—C1—C2—S1	179.69 (14)	C7—C8—C9—C1	178.78 (19)
N1—C1—C2—S1	−0.3 (3)	C2—C1—C9—C8	177.77 (18)
O3—S1—C2—C1	−120.22 (16)	N1—C1—C9—C8	−2.2 (3)
O2—S1—C2—C1	1.78 (19)	C2—C1—C9—C10	−2.0 (3)
O1—S1—C2—C1	122.61 (16)	N1—C1—C9—C10	178.00 (16)
O3—S1—C2—C3	59.42 (16)	C3—C4—C10—C5	179.5 (2)
O2—S1—C2—C3	−178.58 (14)	C3—C4—C10—C9	−1.2 (3)
O1—S1—C2—C3	−57.75 (16)	C6—C5—C10—C4	178.0 (2)
C1—C2—C3—C4	1.4 (3)	C6—C5—C10—C9	−1.2 (3)
S1—C2—C3—C4	−178.30 (17)	C8—C9—C10—C4	−177.23 (18)
C2—C3—C4—C10	−0.8 (3)	C1—C9—C10—C4	2.6 (3)
C10—C5—C6—C7	−0.3 (3)	C8—C9—C10—C5	2.0 (3)
C5—C6—C7—C8	0.9 (3)	C1—C9—C10—C5	−178.18 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (2)	1.94 (2)	2.762 (2)	160.4 (18)
N1—H2N···O2	0.91 (2)	1.83 (2)	2.651 (2)	149.0 (19)
N1—H3N···O3ii	0.87 (3)	2.14 (3)	2.982 (2)	162 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (2)	1.94 (2)	2.762 (2)	160.4 (18)
N1—H2N⋯O2	0.91 (2)	1.83 (2)	2.651 (2)	149.0 (19)
N1—H3N⋯O3ii	0.87 (3)	2.14 (3)	2.982 (2)	162 (2)

Symmetry codes: (i) ; (ii) .