Bis(2-hy­droxy­ethanaminium) naphthalene-1,5-disulfonate

Wang, C.; Yang, S.L.

doi:10.1107/S1600536811023269

organic compounds

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Volume 67| Part 7| July 2011| Page o1847

doi:10.1107/S1600536811023269

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Bis(2-hydroxyethanaminium) naphthalene-1,5-disulfonate

Cong Wang ^a and Sheng Li Yang ^a ^*

^aCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: yslhzzj@sina.com

(Received 30 May 2011; accepted 15 June 2011; online 30 June 2011)

In the crystal structure of the title compound, 2C₂H₈NO⁺·C₁₀H₆O₆S₂²⁻, 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⁺·C₁₀H₆O₆S₂²⁻
M_r = 410.48
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.080
S = 1.04
1718 reflections
122 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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⋯O1^iv	0.93	2.41	3.270 (2)	154
C5—H5⋯O2^v	0.93	2.55	3.459 (2)	167
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z; (iii) x, y-1, z; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811023269/is2725sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811023269/is2725Isup3.cml

checkCIF report

Comment top

Several supramolecular structures of naphthalene-1,5-disulfonate have been reported previously (Russell et al., 1997; Zhang et al., 2005; Gao et al., 2005; Wang et al., 2008). As an extension of research, we report here the synthesis and structure of the title compound, (I) (Table 1 & Fig. 1).

The naphthalene-1,5-disulfonate anion is linked to the ethanolaminium cation by O2—H4'···O4 hydrogen bond (Fig. 1 & Table 1). The crystal structure is further built by N—H···O and C—H···O hydrogen bonds. (Fig. 2 & Table 1). Due to steric hindrance of sulfonate, the nearest centroid separation between naphthalene rings is of 5.264 (3) Å, suggesting no π–π stacking. The arrangement of naphthalene rings is very similar to those observed in previous cases (Sakwa & Wheeler, 2003; Li & Chai, 2007; Wang et al., 2008), but is different from that in bis(oxonium monohydrate) naphthalene-1,5-disulfonate, which shows a partial π–π stacking.

Related literature top

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 top

Naphthalene-1,5-disulfonic acid (5.1 g) and ethanolamine (1.2 g) in a molar ratio of 1:1 were mixed and dissolved in sufficient ethanol by heating to 373 K, at which point a clear solution resulted. The system was then cooled slowly to room temperature. Crystals of (I) (4.7 g) were formed, collected and washed with ethanol.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. The unlabeled half of naphthalene-1,5-disulfonate anion are generated from the labeled half by symmetry operation of (1 - x, 2 - y, - z). The O—H···O hydrogen bond is illustrated as a dashed line.
	Fig. 2. The crystal packing of the title compound, viewed down the c axis. Hydrogen bonds are drawn as dashed lines.

Bis(2-hydroxyethanaminium) naphthalene-1,5-disulfonate top

Crystal data top

2C₂H₈NO⁺·C₁₀H₆O₆S₂²⁻	F(000) = 432.0
M_r = 410.48	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0441P)² + 0.3961P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
1718 reflections	Δρ_max = 0.43 e Å⁻³
122 parameters	Δρ_min = −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)

Crystal data top

2C₂H₈NO⁺·C₁₀H₆O₆S₂²⁻	V = 878.9 (2) Å³
M_r = 410.48	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7946 (14) Å	µ = 0.35 mm⁻¹
b = 8.9011 (13) Å	T = 293 K
c = 10.4050 (16) Å	0.42 × 0.34 × 0.30 mm
β = 104.334 (2)°

Data collection top

Bruker APEX area-detector diffractometer	1718 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1625 reflections with I > 2σ(I)
T_min = 0.855, T_max = 0.898	R_int = 0.019
4721 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	1 restraint
wR(F²) = 0.080	H-atom parameters constrained
S = 1.04	Δρ_max = 0.43 e Å⁻³
1718 reflections	Δρ_min = −0.34 e Å⁻³
122 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.89	1.96	2.837 (2)	168
C3—H3···O1^v	0.93	2.41	3.270 (2)	154
C5—H5···O2^vi	0.93	2.55	3.459 (2)	167

Symmetry codes: (ii) x, −y+1/2, z+1/2; (iii) −x+2, −y+1, −z; (iv) x, y−1, z; (v) x, −y+3/2, z+1/2; (vi) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	2C₂H₈NO⁺·C₁₀H₆O₆S₂²⁻
M_r	410.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.7946 (14), 8.9011 (13), 10.4050 (16)
β (°)	104.334 (2)
V (Å³)	878.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.42 × 0.34 × 0.30

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.855, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	4721, 1718, 1625
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.080, 1.04
No. of reflections	1718
No. of parameters	122
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.34

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.93	2.41	3.270 (2)	154
C5—H5···O2^v	0.93	2.55	3.459 (2)	167

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y+1, −z; (iii) x, y−1, z; (iv) x, −y+3/2, z+1/2; (v) x, −y+3/2, z−1/2.

References

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1847

doi:10.1107/S1600536811023269

Open

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