3,3′-Dichloro­biphenyl-4,4′-diaminium sulfate

Hui-Fen Qian; Wei Huang

doi:10.1107/S1600536811027905

. 2011 Jul 16;67(Pt 8):o2059. doi: 10.1107/S1600536811027905

3,3′-Dichlorobiphenyl-4,4′-diaminium sulfate

Hui-Fen Qian ^a,^*, Wei Huang ^b

PMCID: PMC3213505 PMID: 22091084

Abstract

In the title compound, C₁₂H₁₂Cl₂N₂ ²⁺·SO₄ ²⁻, the two rings are not coplanar [dihedral angle = 48.7 (2)°]. In the crystal, multiple N—H⋯O hydrogen-bond interactions are found between the ammonium and sulfate groups.

Related literature

For related compounds, see: Chawdhury et al. (1968 ▶); Chu et al. (2007 ▶); Dobrzycki & Wozniak (2007 ▶); You et al. (2009 ▶).

Experimental

Crystal data

C₁₂H₁₂Cl₂N₂ ²⁺·SO₄ ²⁻
M _r = 351.20
Triclinic,
a = 6.5475 (11) Å
b = 7.9353 (13) Å
c = 13.363 (2) Å
α = 82.300 (2)°
β = 81.309 (3)°
γ = 88.765 (2)°
V = 680.12 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 291 K
0.12 × 0.12 × 0.10 mm

Data collection

Bruker 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.926, T _max = 0.939
3484 measured reflections
2369 independent reflections
1825 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.091
S = 1.00
2369 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027905/ff2021sup1.cif

e-67-o2059-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027905/ff2021Isup2.hkl

e-67-o2059-Isup2.hkl^{(116.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811027905/ff2021Isup3.cml

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—H1A⋯O3ⁱ	0.89	1.78	2.668 (3)	173
N1—H1B⋯O2	0.89	2.10	2.874 (3)	144
N1—H1C⋯O4ⁱⁱ	0.89	1.90	2.775 (3)	167
N2—H2A⋯O4ⁱⁱⁱ	0.89	1.90	2.781 (3)	172
N2—H2B⋯O2^iv	0.89	1.99	2.865 (3)	166
N2—H2C⋯O3^v	0.89	2.06	2.938 (3)	168

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

Acknowledgments

We acknowledge the National Natural Science Foundation of China (No. 20871065) and the Jiangsu Province Department of Science and Technology (No. BK2009226) for financial aid.

supplementary crystallographic information

Comment

There have been two single-crystal structural investigations on 4,4'-diamino-3,3'-dichlorobiphenyl, namely 4,4'-diamino-3,3'-dichlorobiphenyl (Chawdhury et al., 1968) and 4,4'-Diammonio-3,3'-dichlorobiphenyl dichloride (Dobrzycki & Wozniak, 2007). We have previously reported the single-crystal structures of 2-aminobenzimidazolium hydrogen sulfate (You et al., 2009) and (1R,3S)-1,2,2-trimethylcyclopentane-1,3-diammonium sulfate (Chu et al., 2007). In this work, we describe the single-crystal structure of a sulfate salt of 4,4'-diamino-3,3'-dichlorobiphenyl.

The atom-numbering scheme of the title salt is shown in Fig. 1. The two phenyl rings are not coplanar with a dihedral angle of 48.7 (2)°. In the crystal packing, multiple N—H···O hydrogen-bond interactions are found between the ammonio and sulfate groups.

Experimental

The treatment of 4,4'-diamino-3,3'-dichlorobiphenyl dissolved in methanol with an excess of sulfuric acid yields the title compound. Single crystals suitable for X-ray diffraction measurement were obtained after 5 days' slow evaporation of the mother liquid at room temperature in air. Anal. Calcd. For C₁₂H₁₂N₂Cl₂²⁺.SO₄^2-: C, 41.04; H, 3.44; N, 7.98%. Found: C, 41.22; H, 3.63; N, 7.79%.