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

Weiwei SiMa

doi:10.1107/S1600536810027443

. 2010 Jul 17;66(Pt 8):o2042. doi: 10.1107/S1600536810027443

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

Weiwei SiMa ^a,^*

PMCID: PMC3007199 PMID: 21588350

Abstract

The title ion pair, C₁₈H₁₉N₂O⁺·NO₃ ⁻, features an N—H⋯O hydrogen bond linking the cation to the anion. The morpholine portion adopts a chair conformation; the aromatic rings of the biphenylene portion are twisted [torsion angles for the four atoms involving the aryl–aryl bond = 35.1 (2)–40.4 (2)°].

Related literature

For the synthesis, see: Li et al. (2008 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C₁₈H₁₉N₂O⁺·NO₃ ⁻
M _r = 341.36
Monoclinic,
a = 12.670 (6) Å
b = 13.120 (5) Å
c = 10.865 (5) Å
β = 110.927 (8)°
V = 1687.0 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.981, T _max = 0.981
18242 measured reflections
3852 independent reflections
2848 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.178
S = 1.17
3852 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.24 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810027443/ng2795sup1.cif

e-66-o2042-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027443/ng2795Isup2.hkl

e-66-o2042-Isup2.hkl^{(188.8KB, 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—H2A⋯O2	0.91	1.88	2.784 (2)	172

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Acknowledgments

The author acknowledges the starter fund of Southeast University for the purchase of the X-ray diffractometer.

supplementary crystallographic information

Comment

As a continuation of our study of dielectric-ferroelectric materials, including organic ligands (Li et al., 2008), metal-organic coordination compounds (Zhang et al., 2009), organic-inorganic hybrids, we are interested in the dielectric properties (capacitance and dielectric loss measurements) of the title compound(I), unfortunately, there was no distinct anomaly observed from 93 K to 350 K. In thisarticle, the crystal structure of (I) has been presented.

The asymmetric unit of the title compound consists of one 4'-morpholinemethylbiphenyl-2-carbonitrile cation and one nitrate e-66-o2042-fig1). The intermolecular N—H···O, N—H···N hydrogen bonds link the cations and anions to chains along be-66-o2042-fig2), and make great contribution to the stability of the structure.The title compound crystallizes in the monoclinic system, space groupP2₁/c.

Experimental

4'-morpholinemethylbiphenyl-2-carbonitrile (10 mmol)was dissolved in 10 ml e thanol, to which nitrate acid(10 mmol) was added dropwise under stirring, the reaction solution was stirred for a few minutes.water was added untill all suspended substrates disappeared. Colorless crystals suitable for X-ray analysis were formed after several days by slow evaporation of the solvent at room temperature.