1-Dec­yloxy-4-nitro­benzene

Xi-Gui Yue

doi:10.1107/S160053680903921X

. 2009 Oct 3;65(Pt 11):o2627. doi: 10.1107/S160053680903921X

1-Decyloxy-4-nitrobenzene

Xi-Gui Yue ^a,^*

PMCID: PMC2970962 PMID: 21578243

Abstract

The title compound, C₁₆H₂₅NO₃, has a zigzag decyloxy chain para to the nitro group of the aromatic ring. There are two independent molecules; the two rings are aligned at 48.15 (7)°. In the crystal, weak C—H⋯O hydrogen bonds lead to the formation of infinite chains.

Related literature

For structures of analogs of the title compound, see: McBurney et al. (2004 ▶).

Experimental

Crystal data

C₁₆H₂₅NO₃
M _r = 279.37
Triclinic,
a = 5.642 (3) Å
b = 16.065 (8) Å
c = 19.135 (7) Å
α = 107.410 (16)°
β = 90.610 (16)°
γ = 99.780 (18)°
V = 1627.4 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 K
0.20 × 0.19 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.984, T _max = 0.987
15990 measured reflections
7274 independent reflections
3970 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.176
S = 0.97
7274 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903921X/ng2644sup1.cif

e-65-o2627-sup1.cif^{(25.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903921X/ng2644Isup2.hkl

e-65-o2627-Isup2.hkl^{(355.9KB, 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
C6—H6⋯O2ⁱ	0.93	2.53	3.378 (3)	152
C7—H7B⋯O5ⁱⁱ	0.97	2.77	3.263 (3)	112
C18—H18⋯O4ⁱⁱⁱ	0.93	2.60	3.379 (3)	141
C21—H21⋯O1^iv	0.93	2.70	3.346 (3)	127
C22—H22⋯O1^iv	0.93	2.79	3.381 (3)	123

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

supplementary crystallographic information

Comment

The hydroxy H atom of 4-nitropheno can be substituted by multifarious groups to form many ramifications(McBurney et al., 2004). We have synthesized the analogs using different alkyl as terminal groups and report here the molecular and crystal structures of the title compound, (I).

The title compound, (I), as shown in Fig. 1, crystallizes in space group P-1 and each asymmetric unit consists of two crystallographically independent 1-(decyloxy)-4-nitrobenzene. The angles of the two benzene rings (C1—C6 and C17—C22) in the same asymmetric unit is 48.15 (7) °. All nitryl oxygen atoms are engaged in C—H···O (2.53 (2), 2.60 (2), 2.70 (2), 2.77 (2), 2.79 (2) Å) hydrogen bonds. The weak C—H···O hydrogen bonds link the crystal into a two-dimensional network.

Experimental

1-(decyloxy)-4-nitrobenzene was prepared by adding 4-nitrophenol (0.14 g, 1 mmol), decyl iodide (0.27 g, 1 mmol) and acetone(15 ml) into 10 ml of 8% sodium hydroxide solution. The resultant mixture was heated for 2 h under reflux, then the solution was cooled to room temperaure in an ice bath with stirring. The colorless products were obtained by recrystallized the crude solid from 95% ethanol.