Ethane-1,2-diammonium naphthalene-1,5-disulfonate.

In the crystal structure of the title salt, C(2)H(10)N(2) (2+)·C(10)H(6)O(6)S(2) (2-), both the cation and anion lie on special positions of site symmetry. These are linked by N-H⋯O and N-H⋯(O,O) hydrogen bonds, forming a layer structure.

Related literature

For the crystal structures of ammonium 1,5-naphthalene­disulfonates, see, for example: Russel et al. (1997 ▶); Sakwa & Wheeler (2003 ▶); Zhang et al. (2004 ▶).

Experimental

Crystal data

C2H10N2 2+·C10H6O6S2 2−

M = 348.39

Monoclinic,

a = 11.188 (7) Å

b = 8.230 (4) Å

c = 8.492 (6) Å

β = 100.19 (3)°

V = 769.6 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 293 K

0.31 × 0.27 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.892, T max = 0.919

7310 measured reflections

1759 independent reflections

1599 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.097

S = 1.06

1759 reflections

112 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.23 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039762/xu2622sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039762/xu2622Isup2.hkl

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

C2H10N22+·C10H6O6S22−	F(000) = 364
Mr = 348.39	Dx = 1.503 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6820 reflections
a = 11.188 (7) Å	θ = 3.1–27.5°
b = 8.230 (4) Å	µ = 0.38 mm−1
c = 8.492 (6) Å	T = 293 K
β = 100.19 (3)°	Prism, colorless
V = 769.6 (8) Å3	0.31 × 0.27 × 0.23 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	1759 independent reflections
Radiation source: fine-focus sealed tube	1599 reflections with I > 2σ(I)
graphite	Rint = 0.012
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.892, Tmax = 0.919	k = −9→10
7310 measured reflections	l = −11→11

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.1775P] where P = (Fo2 + 2Fc2)/3
1759 reflections	(Δ/σ)max = 0.001
112 parameters	Δρmax = 0.42 e Å−3
3 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.80614 (3)	0.49980 (4)	0.49518 (4)	0.02704 (14)
O1	0.83952 (9)	0.58324 (13)	0.64845 (12)	0.0385 (3)
O2	0.82188 (9)	0.32459 (13)	0.51712 (14)	0.0415 (3)
O3	0.86701 (9)	0.56466 (15)	0.37277 (13)	0.0406 (3)
N1	0.98833 (11)	0.32604 (14)	0.85576 (14)	0.0297 (3)
C1	0.64836 (11)	0.53300 (16)	0.43172 (15)	0.0262 (3)
C2	0.61199 (13)	0.6030 (2)	0.28556 (18)	0.0388 (3)
H2	0.6693	0.6333	0.2240	0.047*
C3	0.48746 (14)	0.6294 (2)	0.22779 (19)	0.0450 (4)
H3	0.4629	0.6766	0.1278	0.054*
C4	0.40295 (12)	0.58634 (18)	0.31707 (17)	0.0349 (3)
H4	0.3212	0.6047	0.2771	0.042*
C5	0.43711 (11)	0.51406 (14)	0.46991 (16)	0.0239 (3)
C6	1.04788 (12)	0.44939 (17)	0.96990 (16)	0.0310 (3)
H6A	1.0988	0.5190	0.9175	0.037*
H6B	1.0990	0.3962	1.0593	0.037*
H11	0.9543 (15)	0.367 (2)	0.7649 (14)	0.041 (5)*
H12	1.0407 (14)	0.254 (2)	0.835 (2)	0.048 (5)*
H13	0.9362 (13)	0.2720 (19)	0.8978 (19)	0.041 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0183 (2)	0.0338 (2)	0.0301 (2)	0.00095 (10)	0.00700 (14)	0.00333 (11)
O1	0.0296 (5)	0.0519 (6)	0.0336 (5)	−0.0094 (4)	0.0046 (4)	−0.0029 (4)
O2	0.0324 (5)	0.0361 (6)	0.0585 (7)	0.0095 (4)	0.0152 (5)	0.0056 (5)
O3	0.0255 (5)	0.0610 (7)	0.0380 (6)	−0.0009 (5)	0.0130 (4)	0.0098 (5)
N1	0.0320 (6)	0.0295 (6)	0.0288 (5)	0.0020 (5)	0.0085 (4)	0.0005 (4)
C1	0.0195 (6)	0.0303 (6)	0.0293 (6)	0.0013 (5)	0.0058 (4)	0.0031 (5)
C2	0.0265 (6)	0.0556 (9)	0.0362 (7)	0.0008 (6)	0.0110 (5)	0.0172 (6)
C3	0.0312 (7)	0.0663 (10)	0.0371 (8)	0.0055 (7)	0.0056 (6)	0.0266 (7)
C4	0.0230 (6)	0.0473 (8)	0.0336 (7)	0.0040 (6)	0.0027 (5)	0.0126 (6)
C5	0.0207 (6)	0.0249 (6)	0.0268 (6)	0.0012 (4)	0.0060 (5)	0.0026 (4)
C6	0.0294 (7)	0.0322 (6)	0.0325 (7)	0.0010 (6)	0.0087 (5)	−0.0031 (5)

S1—O3	1.4421 (12)	C2—H2	0.9300
S1—O1	1.4606 (14)	C3—C4	1.359 (2)
S1—O2	1.4606 (13)	C3—H3	0.9300
S1—C1	1.7733 (17)	C4—C5	1.417 (2)
N1—C6	1.4784 (19)	C4—H4	0.9300
N1—H11	0.867 (9)	C5—C5i	1.428 (3)
N1—H12	0.870 (9)	C5—C1i	1.4300 (18)
N1—H13	0.860 (9)	C6—C6ii	1.516 (3)
C1—C2	1.363 (2)	C6—H6A	0.9700
C1—C5i	1.4300 (18)	C6—H6B	0.9700
C2—C3	1.410 (2)
O3—S1—O1	112.91 (8)	C3—C2—H2	120.0
O3—S1—O2	113.31 (7)	C4—C3—C2	120.52 (13)
O1—S1—O2	110.14 (7)	C4—C3—H3	119.7
O3—S1—C1	107.19 (7)	C2—C3—H3	119.7
O1—S1—C1	106.39 (7)	C3—C4—C5	121.23 (13)
O2—S1—C1	106.38 (6)	C3—C4—H4	119.4
C6—N1—H11	113.1 (12)	C5—C4—H4	119.4
C6—N1—H12	110.9 (13)	C4—C5—C5i	118.99 (14)
H11—N1—H12	106.8 (17)	C4—C5—C1i	123.28 (12)
C6—N1—H13	110.1 (12)	C5i—C5—C1i	117.73 (15)
H11—N1—H13	110.4 (16)	N1—C6—C6ii	109.58 (15)
H12—N1—H13	105.3 (17)	N1—C6—H6A	109.8
C2—C1—C5i	121.56 (12)	C6ii—C6—H6A	109.8
C2—C1—S1	117.55 (10)	N1—C6—H6B	109.8
C5i—C1—S1	120.89 (10)	C6ii—C6—H6B	109.8
C1—C2—C3	119.96 (13)	H6A—C6—H6B	108.2
C1—C2—H2	120.0
O3—S1—C1—C2	2.51 (14)	C5i—C1—C2—C3	−0.5 (2)
O1—S1—C1—C2	123.56 (13)	S1—C1—C2—C3	178.79 (14)
O2—S1—C1—C2	−119.01 (13)	C1—C2—C3—C4	0.4 (3)
O3—S1—C1—C5i	−178.25 (11)	C2—C3—C4—C5	0.0 (3)
O1—S1—C1—C5i	−57.19 (13)	C3—C4—C5—C5i	−0.2 (2)
O2—S1—C1—C5i	60.24 (12)	C3—C4—C5—C1i	179.91 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1	0.87 (1)	2.31 (1)	3.052 (2)	144 (2)
N1—H11···O2	0.87 (1)	2.38 (1)	3.137 (3)	147 (2)
N1—H12···O1iii	0.87 (1)	1.93 (1)	2.7800 (19)	164 (2)
N1—H13···O2iv	0.86 (1)	1.94 (1)	2.790 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O1	0.87 (1)	2.31 (1)	3.052 (2)	144 (2)
N1—H11⋯O2	0.87 (1)	2.38 (1)	3.137 (3)	147 (2)
N1—H12⋯O1i	0.87 (1)	1.93 (1)	2.7800 (19)	164 (2)
N1—H13⋯O2ii	0.86 (1)	1.94 (1)	2.790 (2)	171 (2)

Symmetry codes: (i) ; (ii) .