Bis(4,4′-methyl­enedianilinium) naphthalene-1,5-disulfonate dihydrate

Lin-Heng Wei

doi:10.1107/S160053680800723X

. 2008 Mar 20;64(Pt 4):o734. doi: 10.1107/S160053680800723X

Bis(4,4′-methylenedianilinium) naphthalene-1,5-disulfonate dihydrate

Lin-Heng Wei ^a,^*

PMCID: PMC2961067 PMID: 21202124

Abstract

The asymmetric unit of the title salt, C₁₃H₁₆N₂ ²⁺·C₁₀H₆O₆S₂ ²⁻·2H₂O, consists of one dication located on a general position, half each of two centrosymmetric dianions, and two uncoordinated water molecules in general positions. In the dication, the dihedral angle between the benzene rings is 74.67 (6)°. The cations and anions interact through N—H⋯O hydrogen bonds. The NH₃ ⁺ functional groups are also involved in N—H⋯O hydrogen bonds with the water molecules, forming an infinite three-dimensional framework in the crystal structure.

Related literature

For related literature, see: Wang & Wei (2007 ▶).

Experimental

Crystal data

C₁₃H₁₆N₂ ²⁺·C₁₀H₆O₆S₂ ²⁻·2H₂O
M _r = 522.58
Triclinic,
a = 7.9652 (6) Å
b = 10.9135 (8) Å
c = 13.8158 (10) Å
α = 87.429 (1)°
β = 85.820 (1)°
γ = 83.262 (1)°
V = 1188.72 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 (2) K
0.13 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.966, T _max = 0.978
12513 measured reflections
4644 independent reflections
3999 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.117
S = 1.08
4644 reflections
334 parameters
30 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800723X/bh2163sup1.cif

e-64-0o734-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800723X/bh2163Isup2.hkl

e-64-0o734-Isup2.hkl^{(227.5KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1ⁱ	0.89	1.91	2.770 (2)	162
N1A—H1A1⋯O5ⁱⁱ	0.89	2.03	2.897 (3)	163
N1—H1C⋯O1Wⁱ	0.89	2.07	2.948 (3)	167
N1A—H1A2⋯O2Wⁱⁱⁱ	0.89	1.86	2.739 (3)	171
N1A—H1A3⋯O1Wⁱⁱⁱ	0.89	1.95	2.807 (3)	161
O1W—H1WA⋯O4ⁱ	0.860 (10)	1.801 (10)	2.645 (2)	166 (2)
O1W—H1WB⋯O6^iv	0.854 (10)	1.957 (11)	2.807 (2)	174 (3)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

supplementary crystallographic information

Comment

This work continues our previous synthetic and structural studies of supramolecular interactions in aromatic molecular salts and adducts (Wang & Wei, 2007). Herein we report the structure of the title salt, (I).

The title complex, (I), consists of one crystallographically independent 4,4'-diphenylmethylendiammonium dication, two water molecules and two independent half naphthalene-1,5-disulfonate dianions. In the dication, the dihedral angle between benzene rings is 74.67 (6)°, and central C1—C7—C1A angle is 112.23 (16)° (Fig. 1). Each dianion is placed on an inversion centre. The 4,4'-diphenylmethylendiammonium dication interact with two naphthalene-1,5-disulfonate dianions through N—H···O hydrogen bonds. These units are further linked by water molecules into an infinite three-dimensional framework by hydrogen bonds (Fig. 2).

Experimental

A 5 ml e thanol solution of 4,4'-methylene-bis(benzenamine) (0.5 mmol, 0.10 g) was added to an aqueous solution (25 ml) of naphthalene-1,5-disulfonic acid (0.50 mmol, 0.15 g). The mixture was stirred for 10 min. at 373 K. The solution was filtered, and the filtrate was allowed to stand at room temperature. After several days, colourless crystals suitable for X-ray diffraction were obtained.