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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2658.
Published online 2009 October 7. doi:  10.1107/S1600536809039762
PMCID: PMC2971418

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

Abstract

In the crystal structure of the title salt, C2H10N2 2+·C10H6O6S2 2−, both the cation and anion lie on special positions of An external file that holds a picture, illustration, etc.
Object name is e-65-o2658-efi1.jpg 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 [triangle]); Sakwa & Wheeler (2003 [triangle]); Zhang et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2658-scheme1.jpg

Experimental

Crystal data

  • C2H10N2 2+·C10H6O6S2 2−
  • M r = 348.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2658-efi2.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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%.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The ammonium H-atoms were refined with a distance restraint of N–H 0.86±0.01 Å; their temperature factors were refined.

Figures

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

Crystal data

C2H10N22+·C10H6O6S22F(000) = 364
Mr = 348.39Dx = 1.503 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6820 reflections
a = 11.188 (7) Åθ = 3.1–27.5°
b = 8.230 (4) ŵ = 0.38 mm1
c = 8.492 (6) ÅT = 293 K
β = 100.19 (3)°Prism, colorless
V = 769.6 (8) Å30.31 × 0.27 × 0.23 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID IP diffractometer1759 independent reflections
Radiation source: fine-focus sealed tube1599 reflections with I > 2σ(I)
graphiteRint = 0.012
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −14→14
Tmin = 0.892, Tmax = 0.919k = −9→10
7310 measured reflectionsl = −11→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0652P)2 + 0.1775P] where P = (Fo2 + 2Fc2)/3
1759 reflections(Δ/σ)max = 0.001
112 parametersΔρmax = 0.42 e Å3
3 restraintsΔρmin = −0.23 e Å3

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

xyzUiso*/Ueq
S10.80614 (3)0.49980 (4)0.49518 (4)0.02704 (14)
O10.83952 (9)0.58324 (13)0.64845 (12)0.0385 (3)
O20.82188 (9)0.32459 (13)0.51712 (14)0.0415 (3)
O30.86701 (9)0.56466 (15)0.37277 (13)0.0406 (3)
N10.98833 (11)0.32604 (14)0.85576 (14)0.0297 (3)
C10.64836 (11)0.53300 (16)0.43172 (15)0.0262 (3)
C20.61199 (13)0.6030 (2)0.28556 (18)0.0388 (3)
H20.66930.63330.22400.047*
C30.48746 (14)0.6294 (2)0.22779 (19)0.0450 (4)
H30.46290.67660.12780.054*
C40.40295 (12)0.58634 (18)0.31707 (17)0.0349 (3)
H40.32120.60470.27710.042*
C50.43711 (11)0.51406 (14)0.46991 (16)0.0239 (3)
C61.04788 (12)0.44939 (17)0.96990 (16)0.0310 (3)
H6A1.09880.51900.91750.037*
H6B1.09900.39621.05930.037*
H110.9543 (15)0.367 (2)0.7649 (14)0.041 (5)*
H121.0407 (14)0.254 (2)0.835 (2)0.048 (5)*
H130.9362 (13)0.2720 (19)0.8978 (19)0.041 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0183 (2)0.0338 (2)0.0301 (2)0.00095 (10)0.00700 (14)0.00333 (11)
O10.0296 (5)0.0519 (6)0.0336 (5)−0.0094 (4)0.0046 (4)−0.0029 (4)
O20.0324 (5)0.0361 (6)0.0585 (7)0.0095 (4)0.0152 (5)0.0056 (5)
O30.0255 (5)0.0610 (7)0.0380 (6)−0.0009 (5)0.0130 (4)0.0098 (5)
N10.0320 (6)0.0295 (6)0.0288 (5)0.0020 (5)0.0085 (4)0.0005 (4)
C10.0195 (6)0.0303 (6)0.0293 (6)0.0013 (5)0.0058 (4)0.0031 (5)
C20.0265 (6)0.0556 (9)0.0362 (7)0.0008 (6)0.0110 (5)0.0172 (6)
C30.0312 (7)0.0663 (10)0.0371 (8)0.0055 (7)0.0056 (6)0.0266 (7)
C40.0230 (6)0.0473 (8)0.0336 (7)0.0040 (6)0.0027 (5)0.0126 (6)
C50.0207 (6)0.0249 (6)0.0268 (6)0.0012 (4)0.0060 (5)0.0026 (4)
C60.0294 (7)0.0322 (6)0.0325 (7)0.0010 (6)0.0087 (5)−0.0031 (5)

Geometric parameters (Å, °)

S1—O31.4421 (12)C2—H20.9300
S1—O11.4606 (14)C3—C41.359 (2)
S1—O21.4606 (13)C3—H30.9300
S1—C11.7733 (17)C4—C51.417 (2)
N1—C61.4784 (19)C4—H40.9300
N1—H110.867 (9)C5—C5i1.428 (3)
N1—H120.870 (9)C5—C1i1.4300 (18)
N1—H130.860 (9)C6—C6ii1.516 (3)
C1—C21.363 (2)C6—H6A0.9700
C1—C5i1.4300 (18)C6—H6B0.9700
C2—C31.410 (2)
O3—S1—O1112.91 (8)C3—C2—H2120.0
O3—S1—O2113.31 (7)C4—C3—C2120.52 (13)
O1—S1—O2110.14 (7)C4—C3—H3119.7
O3—S1—C1107.19 (7)C2—C3—H3119.7
O1—S1—C1106.39 (7)C3—C4—C5121.23 (13)
O2—S1—C1106.38 (6)C3—C4—H4119.4
C6—N1—H11113.1 (12)C5—C4—H4119.4
C6—N1—H12110.9 (13)C4—C5—C5i118.99 (14)
H11—N1—H12106.8 (17)C4—C5—C1i123.28 (12)
C6—N1—H13110.1 (12)C5i—C5—C1i117.73 (15)
H11—N1—H13110.4 (16)N1—C6—C6ii109.58 (15)
H12—N1—H13105.3 (17)N1—C6—H6A109.8
C2—C1—C5i121.56 (12)C6ii—C6—H6A109.8
C2—C1—S1117.55 (10)N1—C6—H6B109.8
C5i—C1—S1120.89 (10)C6ii—C6—H6B109.8
C1—C2—C3119.96 (13)H6A—C6—H6B108.2
C1—C2—H2120.0
O3—S1—C1—C22.51 (14)C5i—C1—C2—C3−0.5 (2)
O1—S1—C1—C2123.56 (13)S1—C1—C2—C3178.79 (14)
O2—S1—C1—C2−119.01 (13)C1—C2—C3—C40.4 (3)
O3—S1—C1—C5i−178.25 (11)C2—C3—C4—C50.0 (3)
O1—S1—C1—C5i−57.19 (13)C3—C4—C5—C5i−0.2 (2)
O2—S1—C1—C5i60.24 (12)C3—C4—C5—C1i179.91 (15)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H11···O10.87 (1)2.31 (1)3.052 (2)144 (2)
N1—H11···O20.87 (1)2.38 (1)3.137 (3)147 (2)
N1—H12···O1iii0.87 (1)1.93 (1)2.7800 (19)164 (2)
N1—H13···O2iv0.86 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2622).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalClear Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Russel, V. A., Evans, C. C., Li, W. & Ward, M. D. (1997). Science, 5312, 575–579. [PubMed]
  • Sakwa, S. & Wheeler, K. A. (2003). Acta Cryst. C59, o332–o334. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Zhang, X.-L., Chen, X.-M. & Ng, S. W. (2004). Acta Cryst. E60, o455–o456.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography