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

Zhu, Z.-B.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536809039762

organic compounds

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Volume 65| Part 11| November 2009| Page o2658

https://doi.org/10.1107/S1600536809039762

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

Zhi-Biao Zhu,^a Shan Gao ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 28 September 2009; accepted 30 September 2009; online 7 October 2009)

In the crystal structure of the title salt, C₂H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻, both the cation and anion lie on special positions of $[\overline{1}]$ 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

C₂H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻
M_r = 348.39
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.097
S = 1.06
1759 reflections
112 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039762/xu2622Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

To an aqueous solution of sodium naphthalene-1,5-disulfonate (0.58 g, 2 mmol) and ethylenediamine was added cobalt diacetate trihydrate (0.46 g, 2 mmol). The mixture was stirred for 15 min and then filtered. Colorless crystals of the organic salt separated from the solution after a few days. CH&N elemental analysis. Calc. for C₁₀H₁₆N₂O₆S₂: C 37.03, H 4.97, N 8.64%; found: C 37.06, H 4.91, N 8.68%.

Structure description top

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

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [C₁₂H₁₀N₂] [C₁₀H₆O₆S₂] at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₂H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻	F(000) = 364
M_r = 348.39	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0652P)² + 0.1775P] where P = (F_o² + 2F_c²)/3
1759 reflections	(Δ/σ)_max = 0.001
112 parameters	Δρ_max = 0.42 e Å⁻³
3 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻	V = 769.6 (8) Å³
M_r = 348.39	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.188 (7) Å	µ = 0.38 mm⁻¹
b = 8.230 (4) Å	T = 293 K
c = 8.492 (6) Å	0.31 × 0.27 × 0.23 mm
β = 100.19 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1759 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1599 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.919	R_int = 0.012
7310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	3 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.42 e Å⁻³
1759 reflections	Δρ_min = −0.23 e Å⁻³
112 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.86 (1)	1.94 (1)	2.790 (2)	171 (2)

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

Experimental details

Crystal data
Chemical formula	C₂H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻
M_r	348.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.188 (7), 8.230 (4), 8.492 (6)
β (°)	100.19 (3)
V (Å³)	769.6 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.31 × 0.27 × 0.23

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.892, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	7310, 1759, 1599
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.097, 1.06
No. of reflections	1759
No. of parameters	112
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.23

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+3/2; (ii) x, −y+1/2, z+1/2.

Acknowledgements

We thank the Natural Science Foundation of Heilongjiang Province (No. B200501), Heilongjiang University, China, and the University of Malaya for supporting this study.

References

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