4-[(2′-Cyano­biphen­yl-4-yl)meth­yl]morpholin-4-ium tetra­fluoridoborate

Xiu-juan Li; Xian-gang Huang; Kang-jun Li

doi:10.1107/S160053681101186X

. 2011 Apr 7;67(Pt 5):o1061. doi: 10.1107/S160053681101186X

4-[(2′-Cyanobiphenyl-4-yl)methyl]morpholin-4-ium tetrafluoridoborate

Xiu-juan Li ^a,^*, Xian-gang Huang ^a, Kang-jun Li ^a

PMCID: PMC3089242 PMID: 21754387

Abstract

In the crystal structure of the title compound, C₁₈H₁₉N₂O⁺·BF₄ ⁻, bifurcated N—H⋯(F,F) hydrogen bonds link the protonated 4′-morpholinemethylbiphenyl-2-carbonitrile cations and slightly distorted tetrafluoroborate anions. π–π interactions [centroid–centroid distance = 3.805 (3) Å] help to consolidate the packing. The dihedral angle between the benzene rings in the cation is 57.24 (11)°.

Related literature

For a related structure, see: SiMa (2010 ▶).

Experimental

Crystal data

C₁₈H₁₉N₂O⁺·BF₄ ⁻
M _r = 366.16
Triclinic,
a = 9.059 (6) Å
b = 9.859 (8) Å
c = 10.597 (8) Å
α = 76.324 (14)°
β = 83.71 (2)°
γ = 86.50 (3)°
V = 913.5 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.978, T _max = 0.978
9817 measured reflections
4098 independent reflections
3039 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.202
S = 1.06
4098 reflections
239 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101186X/jh2276sup1.cif

e-67-o1061-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101186X/jh2276Isup2.hkl

e-67-o1061-Isup2.hkl^{(200.8KB, 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
N2—H2⋯F1	0.90 (2)	2.14 (2)	2.902 (3)	141 (2)
N2—H2⋯F3	0.90 (2)	2.35 (2)	3.219 (3)	161 (2)

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Acknowledgments

The authors are grateful to RiZhao Polytechnic for support.

supplementary crystallographic information

Comment

The crystal structure of 4'-morpholinemethylbiphenyl-2-carbonitrile with nitrate is known (SiMa, 2010).

The asymmetric unit of the title compound is built up of one 4'-morpholinemethylbiphenyl-2-carbonitrile cation with the dihedral angle of 57.24 (11)° between two benzene rings and one tetrafluoroborate anion (Fig 1). The intermolecular N—H···F hydrogen bonds link the cations and anions to chains (Table 1). The π–π stacking interactions of adjacent cyanobenzene rings with a centroid–centroid distance of 3.805 (3)Å stabilize the crystal structure (Fig 2).

Experimental

Tetrafluoroboric acid(10 mmol) was added dropwise under stirring to a solution of 4'-morpholinemethylbiphenyl-2-carbonitrile (10 mmol) ethanol solution. Water was added until all suspended substrates disappeared. Colorless single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation from the solution at room temperature after 5 d, giving a yield of ca 78%.