Bis(2-hy-droxy-ethanaminium) naphthalene-1,5-disulfonate.

In the crystal structure of the title compound, 2C(2)H(8)NO(+)·C(10)H(6)O(6)S(2) (2-), the anion lies on an inversion centre. The components are held together by O-H⋯O hydrogen bond, forming a 2:1 aggregate. The aggregates are further connected by N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Gao et al. (2005 ▶); Li & Chai (2007 ▶); Russell et al. (1997 ▶); Sakwa & Wheeler (2003 ▶); Wang et al. (2008 ▶); Zhang et al. (2005 ▶).

Experimental

Crystal data

2C2H8NO+·C10H6O6S2 2−

M = 410.48

Monoclinic,

a = 9.7946 (14) Å

b = 8.9011 (13) Å

c = 10.4050 (16) Å

β = 104.334 (2)°

V = 878.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.42 × 0.34 × 0.30 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.855, T max = 0.898

4721 measured reflections

1718 independent reflections

1625 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.04

1718 reflections

122 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023269/is2725sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023269/is2725Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023269/is2725Isup3.cml

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

2C2H8NO+·C10H6O6S22−	F(000) = 432.0
Mr = 410.48	Dx = 1.551 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1567 reflections
a = 9.7946 (14) Å	θ = 2.1–16.1°
b = 8.9011 (13) Å	µ = 0.35 mm−1
c = 10.4050 (16) Å	T = 293 K
β = 104.334 (2)°	Prism, colorless
V = 878.9 (2) Å3	0.42 × 0.34 × 0.30 mm
Z = 2

Bruker APEX area-detector diffractometer	1718 independent reflections
Radiation source: fine-focus sealed tube	1625 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→11
Tmin = 0.855, Tmax = 0.898	k = −7→10
4721 measured reflections	l = −11→12

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.3961P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
1718 reflections	Δρmax = 0.43 e Å−3
122 parameters	Δρmin = −0.34 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (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
O1	0.84543 (12)	0.76241 (16)	−0.12460 (11)	0.0408 (3)
O2	0.75476 (13)	0.65670 (12)	0.04999 (12)	0.0380 (3)
O3	0.89350 (12)	0.88364 (13)	0.09087 (11)	0.0368 (3)
O4	0.85710 (15)	0.38353 (14)	−0.03184 (13)	0.0449 (3)
H4'	0.843 (3)	0.4733 (14)	−0.015 (2)	0.067*
S1	0.79615 (4)	0.79324 (4)	−0.00698 (3)	0.02542 (15)
N1	0.91425 (15)	0.17298 (16)	0.20858 (14)	0.0359 (3)
H1A	0.9313	0.1641	0.2963	0.054*
H1B	0.9898	0.2108	0.1872	0.054*
H1C	0.8947	0.0830	0.1713	0.054*
C1	0.64066 (14)	0.90372 (15)	−0.06386 (14)	0.0232 (3)
C2	0.56077 (14)	0.95467 (15)	0.02605 (13)	0.0223 (3)
C3	0.59815 (15)	0.91921 (17)	0.16367 (14)	0.0266 (3)
H3	0.6775	0.8609	0.1983	0.032*
C4	0.51843 (16)	0.97004 (17)	0.24527 (14)	0.0292 (3)
H4	0.5440	0.9455	0.3349	0.035*
C5	0.60178 (16)	0.94103 (17)	−0.19575 (14)	0.0271 (3)
H5	0.6551	0.9074	−0.2526	0.033*
C6	0.79262 (19)	0.2745 (2)	0.16027 (18)	0.0394 (4)
H6A	0.8137	0.3716	0.2029	0.047*
H6B	0.7112	0.2338	0.1856	0.047*
C7	0.7569 (2)	0.2955 (2)	0.01220 (19)	0.0490 (5)
H7A	0.7502	0.1977	−0.0300	0.059*
H7B	0.6653	0.3433	−0.0157	0.059*

	U11	U22	U33	U12	U13	U23
O1	0.0307 (6)	0.0605 (8)	0.0332 (6)	0.0100 (5)	0.0116 (5)	−0.0071 (6)
O2	0.0458 (7)	0.0233 (6)	0.0464 (7)	0.0058 (5)	0.0145 (5)	0.0026 (5)
O3	0.0315 (6)	0.0343 (6)	0.0396 (6)	0.0016 (5)	−0.0006 (5)	−0.0078 (5)
O4	0.0649 (8)	0.0265 (6)	0.0475 (7)	0.0058 (6)	0.0219 (6)	0.0020 (5)
S1	0.0249 (2)	0.0249 (2)	0.0263 (2)	0.00367 (13)	0.00597 (15)	−0.00329 (13)
N1	0.0386 (7)	0.0330 (7)	0.0368 (7)	−0.0016 (6)	0.0102 (6)	−0.0055 (6)
C1	0.0238 (7)	0.0200 (7)	0.0262 (7)	−0.0003 (5)	0.0070 (5)	−0.0013 (5)
C2	0.0246 (7)	0.0194 (6)	0.0233 (7)	−0.0017 (5)	0.0063 (5)	−0.0007 (5)
C3	0.0274 (7)	0.0253 (7)	0.0261 (7)	0.0033 (6)	0.0050 (6)	0.0025 (6)
C4	0.0361 (8)	0.0305 (8)	0.0210 (7)	0.0014 (6)	0.0068 (6)	0.0026 (6)
C5	0.0325 (8)	0.0252 (7)	0.0256 (7)	0.0004 (6)	0.0109 (6)	−0.0017 (6)
C6	0.0420 (9)	0.0340 (9)	0.0454 (9)	0.0024 (7)	0.0168 (8)	−0.0010 (7)
C7	0.0594 (12)	0.0359 (10)	0.0457 (10)	−0.0083 (8)	0.0016 (9)	0.0037 (8)

O1—S1	1.4485 (11)	C2—C2i	1.429 (3)
O2—S1	1.4533 (12)	C3—C4	1.365 (2)
O3—S1	1.4535 (11)	C3—H3	0.9300
O4—C7	1.417 (2)	C4—C5i	1.406 (2)
O4—H4'	0.835 (10)	C4—H4	0.9300
S1—C1	1.7862 (14)	C5—C4i	1.406 (2)
N1—C6	1.481 (2)	C5—H5	0.9300
N1—H1A	0.8900	C6—C7	1.505 (3)
N1—H1B	0.8900	C6—H6A	0.9700
N1—H1C	0.8900	C6—H6B	0.9700
C1—C5	1.371 (2)	C7—H7A	0.9700
C1—C2	1.4338 (19)	C7—H7B	0.9700
C2—C3	1.423 (2)
C7—O4—H4'	107.6 (18)	C4—C3—H3	119.7
O1—S1—O2	111.79 (8)	C2—C3—H3	119.7
O1—S1—O3	113.50 (7)	C3—C4—C5i	120.96 (13)
O2—S1—O3	112.22 (7)	C3—C4—H4	119.5
O1—S1—C1	105.04 (7)	C5i—C4—H4	119.5
O2—S1—C1	107.12 (7)	C1—C5—C4i	120.20 (13)
O3—S1—C1	106.56 (7)	C1—C5—H5	119.9
C6—N1—H1A	109.5	C4i—C5—H5	119.9
C6—N1—H1B	109.5	N1—C6—C7	112.78 (15)
H1A—N1—H1B	109.5	N1—C6—H6A	109.0
C6—N1—H1C	109.5	C7—C6—H6A	109.0
H1A—N1—H1C	109.5	N1—C6—H6B	109.0
H1B—N1—H1C	109.5	C7—C6—H6B	109.0
C5—C1—C2	121.01 (13)	H6A—C6—H6B	107.8
C5—C1—S1	117.89 (11)	O4—C7—C6	113.31 (16)
C2—C1—S1	121.08 (10)	O4—C7—H7A	108.9
C3—C2—C2i	119.32 (15)	C6—C7—H7A	108.9
C3—C2—C1	122.72 (13)	O4—C7—H7B	108.9
C2i—C2—C1	117.97 (15)	C6—C7—H7B	108.9
C4—C3—C2	120.54 (13)	H7A—C7—H7B	107.7

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4'···O2	0.84 (1)	2.04 (1)	2.840 (2)	160 (2)
N1—H1A···O4ii	0.89	2.13	2.934 (2)	149
N1—H1B···O1iii	0.89	1.90	2.766 (2)	164
N1—H1C···O3iv	0.89	1.96	2.837 (2)	168
C3—H3···O1v	0.93	2.41	3.270 (2)	154
C5—H5···O2vi	0.93	2.55	3.459 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4′⋯O2	0.835 (10)	2.041 (10)	2.840 (2)	160 (2)
N1—H1A⋯O4i	0.89	2.13	2.934 (2)	149
N1—H1B⋯O1ii	0.89	1.90	2.766 (2)	164
N1—H1C⋯O3iii	0.89	1.96	2.837 (2)	168
C3—H3⋯O1iv	0.93	2.41	3.270 (2)	154
C5—H5⋯O2v	0.93	2.55	3.459 (2)	167

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