6-(4-Nitro­phen­oxy)hexa­nol

Muhammad Saif Ullah Khan; Zareen Akhter; Michael Bolte; Sajjad A Cheema; Humaira M Siddiqi

doi:10.1107/S160053680901722X

. 2009 May 14;65(Pt 6):o1285. doi: 10.1107/S160053680901722X

6-(4-Nitrophenoxy)hexanol

Muhammad Saif Ullah Khan ^a, Zareen Akhter ^a,^*, Michael Bolte ^b, Sajjad A Cheema ^c, Humaira M Siddiqi ^a

PMCID: PMC2969679 PMID: 21583147

Abstract

The title compound, C₁₂H₁₇NO₄, features an almost planar molecule (r.m.s. deviation for all non-H atoms = 0.070 Å). All methylene C—C bonds adopt an antiperiplanar conformation. In the crystal structure the molecules lie in planes parallel to (1 Inline graphic 2) and the packing is stabilized by O—H⋯O hydrogen bonds.

Related literature

For background material on polymers and their properties, see: Manners (1999 ▶); Jarzabek et al. (1999 ▶) Schab-Balcerzak et al. (2002 ▶); Choi et al. (2004 ▶); Hsiao & Lin (2004 ▶); Shao et al. (2007 ▶); Shockravi et al. (2007 ▶); Yin et al. (1998 ▶). For studies on a related compound, see: Saeed et al. (2008 ▶).

Experimental

Crystal data

C₁₂H₁₇NO₄
M _r = 239.27
Triclinic,
a = 5.4410 (7) Å
b = 10.2270 (11) Å
c = 11.3333 (14) Å
α = 96.993 (9)°
β = 103.818 (10)°
γ = 99.516 (10)°
V = 595.34 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.25 × 0.24 × 0.12 mm

Data collection

STOE IPDS II diffractometer
Absorption correction: none
5002 measured reflections
2105 independent reflections
1694 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.185
S = 1.04
2105 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S160053680901722X/tk2444sup1.cif

e-65-o1285-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901722X/tk2444Isup2.hkl

e-65-o1285-Isup2.hkl^{(103.5KB, 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
O1—H1⋯O4ⁱ	0.83 (5)	2.10 (5)	2.905 (2)	163 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Department of Chemistry, Quaid-i-Azam University, and the Institute for Inorganic Chemistry, University of Frankfurt, for providing laboratory and analytical facilities.

supplementary crystallographic information

Comment

Polymers are ubiquitous because of their tremendous processing advantage over ceramics and metals (Manners, 1999). Therefore, much research in recent years has focused upon producing speciality polymers with a better balance of properties (Shockravi et al., 2007). The goal can be achieved by inducing desired modifications in the polymer core structure (Saeed et al., 2008). Flexible linkages such as for the aryl-ether moiety (Shao et al., 2007) and/or methylene spacers (Yin et al., 1998) can be introduced into the macro chain in order to obtain desirable polymers. It has been recognized that the incorporation of an aryl-ether moiety generally imparts enhanced solubility and processability while maintaining the toughness of the polymers (Hsiao & Lin, 2004). Moreover, the addition of aliphatic methylene spacers between the aromatic moieties increases the degree of freedom by reducing the segmental barrier and effectively disrupts potential intermolecular interactions (Schab-Balcerzak et al., 2002). Furthermore, the inclusion of these flexible linkages in the polymer core structure also imparts mesogenic (Choi et al., 2004) and optical properties (Jarzabek et al., 1999) to the resulting polymer. Thus, the final polymer produced by the introduction of these linkages exhibits not an enhancement in its processability but also an improvement in its performance (Jarzabek et al., 1999). The title compound, (I), Fig. 1, is a flexible nitro-alcohol precursor with built-in aliphatic (methylene) groups along with aryl-ether moiety, which was prepared as part of our quest to design and synthesize structurally modified monomers for processable high performance polymers (Saeed et al., 2008).

Experimental

The title compound (I) was synthesized by Williamson's etherification of 1,6-hexane diol and p-nitrochlorobenzene. A three-necked round bottom flask equipped with reflux condenser, thermometer and nitrogen inlet was charged with a suspension of 1,6-hexane diol (2.5 g; 21 mmol) and anhydrous potassium carbonate (2.93 g; 21 mmol) in dimethylformamide (60 ml) and stirred for 30 mins. Then p-nitrochlorobenzene (3.33 g; 21 mmol) was added dropwise to the suspension and the resulting mixture was heated to 383 K for 6 h. The reaction mixture was poured into 500 ml of chilled water, cooled to room temperature and the crude product was filtered as a light-yellow solid mass. The product was then washed thoroughly with water, dissolved in ethanol and set aside for crystallization. Yield 74%, m.p. 357 K.