4-(4-Nitro­phen­oxy)butanol

Akhter, Z.; McKee, V.; Saif Ullah Khan, M.; Iftikhar, B.; Siddiqi, H.M.

doi:10.1107/S1600536811007744

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o800

doi:10.1107/S1600536811007744

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4-(4-Nitrophenoxy)butanol

Zareen Akhter,^a ^* Vickie McKee,^b Muhammad Saif Ullah Khan,^a Bushra Iftikhar ^a and Humaira M. Siddiqi ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bChemistry Department, Loughborough University, Loughborough LE11 3TU, England
^*Correspondence e-mail: zareenakhter@yahoo.com

(Received 26 February 2011; accepted 1 March 2011; online 5 March 2011)

The crystal structure of the title compound, C₁₀H₁₃NO₄, features intermolecular O—H⋯O(nitro) hydrogen bonding, which links molecules into supramolecular chains running parallel to the bc diagonal. There is also π–π stacking between 4-nitrophenyl groups, the interplanar distance between the nitrobenzene rings being 3.472 (2) Å.

Related literature

For background material on polymers containing flexible linkages, see: Chandrasekhar (2005 ); Patil et al. (2010 ); Schab-Balcerzak et al. (2002 ); Shahram Mehdipour-Ataei & Zigheimat (2007 ); Scholl et al. (2007 ); Shockravi et al. (2007 ). For studies on related compounds based on flexible monomers, see: Choi et al. (2004 ); Liu et al. (2008 ).

Experimental

Crystal data

C₁₀H₁₃NO₄
M_r = 211.21
Triclinic, $[P \overline 1]$
a = 4.7971 (6) Å
b = 10.6035 (13) Å
c = 11.2523 (14) Å
α = 117.521 (2)°
β = 92.451 (2)°
γ = 94.971 (2)°
V = 503.46 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 150 K
0.44 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.954, T_max = 0.983
5772 measured reflections
2924 independent reflections
2224 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.139
S = 1.06
2924 reflections
139 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3ⁱ	0.80 (3)	2.10 (2)	2.8808 (14)	163 (2)
Symmetry code: (i) x+2, y+1, z+1.

Data collection: APEX2 (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007744/tk2724sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007744/tk2724Isup2.hkl

checkCIF report

Comment top

Polymers are an important class of materials which have either supplemented or replaced conventional substances such as wood, stone, metal, glass and ceramics in modern technological applications (Chandrasekhar, 2005). Therefore, considerable research in recent years has focused upon producing novel polymeric materials with a better balance of physical and chemical properties (Shockravi et al., 2007). Various flexible linkages such as the ether moiety (Patil et al., 2010) and methylene spacers (Scholl et al., 2007) can be introduced into the polymer backbone in order to improve their properties. The incorporation of an aryl-ether moiety is believed to impart enhanced solubility and processability to the polymers while maintaining their toughness (Shahram Mehdipour-Ataei & Zigheimat, 2007). On the other hand, the inclusion of aliphatic methylene spacers in the macrochain increases the degree of freedom by reducing the segmental barrier and effectively disrupts intermolecular interactions (Schab-Balcerzak et al., 2002). Thus, the final polymer prepared from the monomers containing flexible linkages not only exhibits an enhancement in its processability but also shows an improvement in its performance as these flexible linkages also bestow mesogenic (Choi et al., 2004) and optical properties (Liu et al., 2008) to the resulting polymeric materials. The title compound, (I), Fig. 1, is a nitro-alcohol precursor with built-in methylene spacers 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.

The alcohol group is H-bonded to the nitro group of a neighbouring molecule, Table 1. These link molecules into supramolecular chains running along the bc diagonal, Fig. 2. There are π-π interactions between the chains; the interplanar distance between the nitrobenzene rings is 3.472 (2) Å (symmetry operation: x - 1, y, z).

Related literature top

For background to polymers and their properties, see: Chandrasekhar (2005); Patil et al. (2010); Schab-Balcerzak et al. (2002); Shahram Mehdipour-Ataei & Zigheimat (2007); Scholl et al. (2007); Shockravi et al. (2007); For related polymers, see: Choi et al. (2004); Liu et al. (2008).

Experimental top

The title compound (I) was synthesized by Williamson's etherification of 1,4-butane diol and p-nitrochlorobenzene. A three-necked round bottom flask equipped with reflux condenser, thermometer and nitrogen inlet was charged with a suspension of 1,4-butane diol (1.69 ml; 19.1 mmol) and anhydrous potassium carbonate (2.65 g; 19.1 mmol) in dimethylformamide (40 ml) and stirred for 30 min. The resulting mixture was heated to 383–393 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 79%, M.pt. 344 K.

Computing details top

Data collection: APEX2 (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

	Fig. 1. Perspective view of the molecule, showing ellipsoids at the 50% probability level. Hydrogen atoms are shown as arbitrary spheres.
	Fig. 2. Packing diagram viewed down the a axis. Hydrogen atoms have been omitted and the dashed line represent O—H···O hydrogen bonds.

4-(4-Nitrophenoxy)butanol top

Crystal data top

C₁₀H₁₃NO₄	Z = 2
M_r = 211.21	F(000) = 224
Triclinic, P1	D_x = 1.393 Mg m⁻³
Hall symbol: -P 1	Melting point: 416 K
a = 4.7971 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6035 (13) Å	Cell parameters from 1750 reflections
c = 11.2523 (14) Å	θ = 3.6–30.2°
α = 117.521 (2)°	µ = 0.11 mm⁻¹
β = 92.451 (2)°	T = 150 K
γ = 94.971 (2)°	Block, yellow
V = 503.46 (11) Å³	0.44 × 0.21 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	2924 independent reflections
Radiation source: fine-focus sealed tube	2224 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 30.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −6→6
T_min = 0.954, T_max = 0.983	k = −14→14
5772 measured reflections	l = −15→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0693P)² + 0.098P] where P = (F_o² + 2F_c²)/3
2924 reflections	(Δ/σ)_max < 0.001
139 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₀H₁₃NO₄	γ = 94.971 (2)°
M_r = 211.21	V = 503.46 (11) Å³
Triclinic, P1	Z = 2
a = 4.7971 (6) Å	Mo Kα radiation
b = 10.6035 (13) Å	µ = 0.11 mm⁻¹
c = 11.2523 (14) Å	T = 150 K
α = 117.521 (2)°	0.44 × 0.21 × 0.16 mm
β = 92.451 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2924 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	2224 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.983	R_int = 0.018
5772 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.33 e Å⁻³
2924 reflections	Δρ_min = −0.24 e Å⁻³
139 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.44295 (19)	0.42787 (10)	0.15618 (9)	0.0266 (2)
C1	0.2302 (3)	0.33362 (13)	0.06879 (12)	0.0218 (2)
C2	0.1670 (3)	0.34735 (14)	−0.04730 (13)	0.0263 (3)
H2	0.2744	0.4178	−0.0617	0.032*
C3	−0.0513 (3)	0.25860 (14)	−0.14057 (13)	0.0265 (3)
H3	−0.0961	0.2678	−0.2191	0.032*
C4	−0.2045 (3)	0.15560 (13)	−0.11787 (12)	0.0223 (3)
N1	−0.4365 (2)	0.06242 (11)	−0.21523 (11)	0.0252 (2)
O2	−0.4898 (2)	0.07525 (11)	−0.31628 (10)	0.0348 (3)
O3	−0.5727 (2)	−0.02676 (11)	−0.19184 (10)	0.0371 (3)
C5	−0.1435 (3)	0.13965 (13)	−0.00455 (12)	0.0240 (3)
H5	−0.2508	0.0684	0.0087	0.029*
C6	0.0756 (3)	0.22859 (13)	0.08947 (12)	0.0240 (3)
H6	0.1203	0.2182	0.1673	0.029*
C7	0.5221 (3)	0.41461 (14)	0.27521 (13)	0.0261 (3)
H7A	0.5888	0.3204	0.2494	0.031*
H7B	0.3588	0.4228	0.3281	0.031*
C8	0.7545 (3)	0.53402 (14)	0.35747 (13)	0.0265 (3)
H8A	0.9078	0.5294	0.3000	0.032*
H8B	0.8316	0.5188	0.4323	0.032*
C9	0.6588 (3)	0.68272 (14)	0.41563 (13)	0.0281 (3)
H9A	0.5873	0.6991	0.3407	0.034*
H9B	0.5015	0.6865	0.4709	0.034*
C10	0.8899 (3)	0.80179 (15)	0.50147 (13)	0.0298 (3)
H10A	1.0544	0.7956	0.4497	0.036*
H10B	0.8225	0.8961	0.5287	0.036*
O4	0.9673 (3)	0.78689 (13)	0.61746 (11)	0.0442 (3)
H4	1.096 (5)	0.847 (3)	0.661 (2)	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0287 (5)	0.0279 (5)	0.0219 (4)	−0.0073 (4)	−0.0059 (3)	0.0129 (4)
C1	0.0223 (6)	0.0224 (6)	0.0189 (5)	−0.0004 (4)	−0.0003 (4)	0.0088 (5)
C2	0.0293 (6)	0.0286 (6)	0.0235 (6)	−0.0036 (5)	0.0000 (5)	0.0156 (5)
C3	0.0294 (6)	0.0309 (6)	0.0214 (6)	−0.0016 (5)	−0.0011 (5)	0.0154 (5)
C4	0.0216 (6)	0.0225 (6)	0.0198 (5)	0.0002 (4)	−0.0005 (4)	0.0081 (5)
N1	0.0248 (5)	0.0258 (5)	0.0226 (5)	0.0000 (4)	−0.0013 (4)	0.0101 (4)
O2	0.0382 (6)	0.0388 (6)	0.0266 (5)	−0.0028 (4)	−0.0088 (4)	0.0170 (4)
O3	0.0369 (6)	0.0384 (6)	0.0329 (5)	−0.0153 (4)	−0.0073 (4)	0.0183 (5)
C5	0.0263 (6)	0.0244 (6)	0.0226 (6)	−0.0017 (5)	0.0005 (5)	0.0129 (5)
C6	0.0271 (6)	0.0255 (6)	0.0207 (5)	−0.0002 (5)	−0.0006 (5)	0.0128 (5)
C7	0.0272 (6)	0.0287 (6)	0.0226 (6)	0.0002 (5)	−0.0032 (5)	0.0133 (5)
C8	0.0225 (6)	0.0293 (6)	0.0245 (6)	0.0016 (5)	−0.0042 (5)	0.0107 (5)
C9	0.0261 (6)	0.0289 (7)	0.0243 (6)	0.0026 (5)	−0.0036 (5)	0.0088 (5)
C10	0.0339 (7)	0.0294 (7)	0.0223 (6)	−0.0018 (5)	−0.0016 (5)	0.0101 (5)
O4	0.0490 (7)	0.0521 (7)	0.0263 (5)	−0.0254 (5)	−0.0147 (5)	0.0208 (5)

Geometric parameters (Å, º) top

O1—C1	1.3551 (14)	C6—H6	0.9500
O1—C7	1.4484 (14)	C7—C8	1.5120 (17)
C1—C6	1.3984 (17)	C7—H7A	0.9900
C1—C2	1.4033 (16)	C7—H7B	0.9900
C2—C3	1.3805 (18)	C8—C9	1.5240 (19)
C2—H2	0.9500	C8—H8A	0.9900
C3—C4	1.3903 (17)	C8—H8B	0.9900
C3—H3	0.9500	C9—C10	1.5149 (18)
C4—C5	1.3842 (16)	C9—H9A	0.9900
C4—N1	1.4559 (15)	C9—H9B	0.9900
N1—O2	1.2252 (14)	C10—O4	1.4233 (17)
N1—O3	1.2361 (14)	C10—H10A	0.9900
C5—C6	1.3872 (17)	C10—H10B	0.9900
C5—H5	0.9500	O4—H4	0.80 (3)

C1—O1—C7	117.77 (10)	C8—C7—H7A	110.2
O1—C1—C6	123.97 (11)	O1—C7—H7B	110.2
O1—C1—C2	115.82 (11)	C8—C7—H7B	110.2
C6—C1—C2	120.20 (11)	H7A—C7—H7B	108.5
C3—C2—C1	120.07 (11)	C7—C8—C9	113.49 (11)
C3—C2—H2	120.0	C7—C8—H8A	108.9
C1—C2—H2	120.0	C9—C8—H8A	108.9
C2—C3—C4	118.99 (11)	C7—C8—H8B	108.9
C2—C3—H3	120.5	C9—C8—H8B	108.9
C4—C3—H3	120.5	H8A—C8—H8B	107.7
C5—C4—C3	121.74 (11)	C10—C9—C8	113.36 (11)
C5—C4—N1	118.96 (11)	C10—C9—H9A	108.9
C3—C4—N1	119.30 (11)	C8—C9—H9A	108.9
O2—N1—O3	122.62 (11)	C10—C9—H9B	108.9
O2—N1—C4	119.22 (10)	C8—C9—H9B	108.9
O3—N1—C4	118.16 (10)	H9A—C9—H9B	107.7
C4—C5—C6	119.48 (11)	O4—C10—C9	108.37 (11)
C4—C5—H5	120.3	O4—C10—H10A	110.0
C6—C5—H5	120.3	C9—C10—H10A	110.0
C5—C6—C1	119.51 (11)	O4—C10—H10B	110.0
C5—C6—H6	120.2	C9—C10—H10B	110.0
C1—C6—H6	120.2	H10A—C10—H10B	108.4
O1—C7—C8	107.39 (10)	C10—O4—H4	108.2 (17)
O1—C7—H7A	110.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3ⁱ	0.80 (3)	2.10 (2)	2.8808 (14)	163 (2)

Symmetry code: (i) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₄
M_r	211.21
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	4.7971 (6), 10.6035 (13), 11.2523 (14)
α, β, γ (°)	117.521 (2), 92.451 (2), 94.971 (2)
V (Å³)	503.46 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.44 × 0.21 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.954, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	5772, 2924, 2224
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.713

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.139, 1.06
No. of reflections	2924
No. of parameters	139
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.24

Computer programs: APEX2 (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3ⁱ	0.80 (3)	2.10 (2)	2.8808 (14)	163 (2)

Symmetry code: (i) x+2, y+1, z+1.

Acknowledgements

The authors are grateful to the Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and the Chemistry Department, Loughborough University, England, for providing laboratory and analytical facilities.

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