organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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4-(4-Nitro­phen­­oxy)butanol

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 ππ 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[Chandrasekhar, V. (2005). In Inorganic and Organometallic Polymers. Heidelberg: Springer-Verlag.]); Patil et al. (2010[Patil, A. S., Medhi, M., Sadavarte, N. V., Wadgaonkar, P. P. & Maldar, N. N. (2010). Mater. Sci. Eng. B, 168, 111-116.]); Schab-Balcerzak et al. (2002[Schab-Balcerzak, E., Sek, D., Volozhin, A., Chamenko, T. & Jarzabek, B. (2002). Eur. Polym. J. 38, 423-430.]); Shahram Mehdipour-Ataei & Zigheimat (2007[Shahram Mehdipour-Ataei, S. & Zigheimat, F. (2007). Eur. Polym. J. 43, 1020-1026.]); Scholl et al. (2007[Scholl, M., Kadlecova, Z. & Klok, H.-A. (2007). Prog. Polym. Sci. 34, 24-61.]); Shockravi et al. (2007[Shockravi, A., Mehdipour-Ataei, S., Abouzari-Lotf, E. & Zakeri, M. (2007). Eur. Polym. J. 43, 620-627.]). For studies on related compounds based on flexible monomers, see: Choi et al. (2004[Choi, E. J., Ahn, J. C., Chien, L. C., Lee, C. K., Zin, W. C., Kim, D. C. & Shin, S. T. (2004). Macromolecules, 37, 71-78.]); Liu et al. (2008[Liu, Z., Yu, F., Zhang, Q., Zeng, Y. & Wang, Y. (2008). Eur. Polym. J. 44, 2718-2727.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13NO4

  • Mr = 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[Sheldrick, G. M. (2008a). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.954, Tmax = 0.983

  • 5772 measured reflections

  • 2924 independent reflections

  • 2224 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H atoms were placed in calculated positions using a riding model with C—H distances constrained to 0.95 and 0.99 Å for aryl and methylene groups, respectively, and with Uiso(H)=1.2 Ueq(C). The hydrogen bonded to oxygen was located from difference maps; the coordinates were refined freely withUiso(H)=1.5 Ueq(O).

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
[Figure 1] Fig. 1. Perspective view of the molecule, showing ellipsoids at the 50% probability level. Hydrogen atoms are shown as arbitrary spheres.
[Figure 2] 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
C10H13NO4Z = 2
Mr = 211.21F(000) = 224
Triclinic, P1Dx = 1.393 Mg m3
Hall symbol: -P 1Melting point: 416 K
a = 4.7971 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.6035 (13) ÅCell parameters from 1750 reflections
c = 11.2523 (14) Åθ = 3.6–30.2°
α = 117.521 (2)°µ = 0.11 mm1
β = 92.451 (2)°T = 150 K
γ = 94.971 (2)°Block, yellow
V = 503.46 (11) Å30.44 × 0.21 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
2924 independent reflections
Radiation source: fine-focus sealed tube2224 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ϕ and ω scansθmax = 30.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)
h = 66
Tmin = 0.954, Tmax = 0.983k = 1414
5772 measured reflectionsl = 1516
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0693P)2 + 0.098P]
where P = (Fo2 + 2Fc2)/3
2924 reflections(Δ/σ)max < 0.001
139 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C10H13NO4γ = 94.971 (2)°
Mr = 211.21V = 503.46 (11) Å3
Triclinic, P1Z = 2
a = 4.7971 (6) ÅMo Kα radiation
b = 10.6035 (13) ŵ = 0.11 mm1
c = 11.2523 (14) ÅT = 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)
Tmin = 0.954, Tmax = 0.983Rint = 0.018
5772 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.33 e Å3
2924 reflectionsΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
O10.44295 (19)0.42787 (10)0.15618 (9)0.0266 (2)
C10.2302 (3)0.33362 (13)0.06879 (12)0.0218 (2)
C20.1670 (3)0.34735 (14)0.04730 (13)0.0263 (3)
H20.27440.41780.06170.032*
C30.0513 (3)0.25860 (14)0.14057 (13)0.0265 (3)
H30.09610.26780.21910.032*
C40.2045 (3)0.15560 (13)0.11787 (12)0.0223 (3)
N10.4365 (2)0.06242 (11)0.21523 (11)0.0252 (2)
O20.4898 (2)0.07525 (11)0.31628 (10)0.0348 (3)
O30.5727 (2)0.02676 (11)0.19184 (10)0.0371 (3)
C50.1435 (3)0.13965 (13)0.00455 (12)0.0240 (3)
H50.25080.06840.00870.029*
C60.0756 (3)0.22859 (13)0.08947 (12)0.0240 (3)
H60.12030.21820.16730.029*
C70.5221 (3)0.41461 (14)0.27521 (13)0.0261 (3)
H7A0.58880.32040.24940.031*
H7B0.35880.42280.32810.031*
C80.7545 (3)0.53402 (14)0.35747 (13)0.0265 (3)
H8A0.90780.52940.30000.032*
H8B0.83160.51880.43230.032*
C90.6588 (3)0.68272 (14)0.41563 (13)0.0281 (3)
H9A0.58730.69910.34070.034*
H9B0.50150.68650.47090.034*
C100.8899 (3)0.80179 (15)0.50147 (13)0.0298 (3)
H10A1.05440.79560.44970.036*
H10B0.82250.89610.52870.036*
O40.9673 (3)0.78689 (13)0.61746 (11)0.0442 (3)
H41.096 (5)0.847 (3)0.661 (2)0.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0287 (5)0.0279 (5)0.0219 (4)0.0073 (4)0.0059 (3)0.0129 (4)
C10.0223 (6)0.0224 (6)0.0189 (5)0.0004 (4)0.0003 (4)0.0088 (5)
C20.0293 (6)0.0286 (6)0.0235 (6)0.0036 (5)0.0000 (5)0.0156 (5)
C30.0294 (6)0.0309 (6)0.0214 (6)0.0016 (5)0.0011 (5)0.0154 (5)
C40.0216 (6)0.0225 (6)0.0198 (5)0.0002 (4)0.0005 (4)0.0081 (5)
N10.0248 (5)0.0258 (5)0.0226 (5)0.0000 (4)0.0013 (4)0.0101 (4)
O20.0382 (6)0.0388 (6)0.0266 (5)0.0028 (4)0.0088 (4)0.0170 (4)
O30.0369 (6)0.0384 (6)0.0329 (5)0.0153 (4)0.0073 (4)0.0183 (5)
C50.0263 (6)0.0244 (6)0.0226 (6)0.0017 (5)0.0005 (5)0.0129 (5)
C60.0271 (6)0.0255 (6)0.0207 (5)0.0002 (5)0.0006 (5)0.0128 (5)
C70.0272 (6)0.0287 (6)0.0226 (6)0.0002 (5)0.0032 (5)0.0133 (5)
C80.0225 (6)0.0293 (6)0.0245 (6)0.0016 (5)0.0042 (5)0.0107 (5)
C90.0261 (6)0.0289 (7)0.0243 (6)0.0026 (5)0.0036 (5)0.0088 (5)
C100.0339 (7)0.0294 (7)0.0223 (6)0.0018 (5)0.0016 (5)0.0101 (5)
O40.0490 (7)0.0521 (7)0.0263 (5)0.0254 (5)0.0147 (5)0.0208 (5)
Geometric parameters (Å, º) top
O1—C11.3551 (14)C6—H60.9500
O1—C71.4484 (14)C7—C81.5120 (17)
C1—C61.3984 (17)C7—H7A0.9900
C1—C21.4033 (16)C7—H7B0.9900
C2—C31.3805 (18)C8—C91.5240 (19)
C2—H20.9500C8—H8A0.9900
C3—C41.3903 (17)C8—H8B0.9900
C3—H30.9500C9—C101.5149 (18)
C4—C51.3842 (16)C9—H9A0.9900
C4—N11.4559 (15)C9—H9B0.9900
N1—O21.2252 (14)C10—O41.4233 (17)
N1—O31.2361 (14)C10—H10A0.9900
C5—C61.3872 (17)C10—H10B0.9900
C5—H50.9500O4—H40.80 (3)
C1—O1—C7117.77 (10)C8—C7—H7A110.2
O1—C1—C6123.97 (11)O1—C7—H7B110.2
O1—C1—C2115.82 (11)C8—C7—H7B110.2
C6—C1—C2120.20 (11)H7A—C7—H7B108.5
C3—C2—C1120.07 (11)C7—C8—C9113.49 (11)
C3—C2—H2120.0C7—C8—H8A108.9
C1—C2—H2120.0C9—C8—H8A108.9
C2—C3—C4118.99 (11)C7—C8—H8B108.9
C2—C3—H3120.5C9—C8—H8B108.9
C4—C3—H3120.5H8A—C8—H8B107.7
C5—C4—C3121.74 (11)C10—C9—C8113.36 (11)
C5—C4—N1118.96 (11)C10—C9—H9A108.9
C3—C4—N1119.30 (11)C8—C9—H9A108.9
O2—N1—O3122.62 (11)C10—C9—H9B108.9
O2—N1—C4119.22 (10)C8—C9—H9B108.9
O3—N1—C4118.16 (10)H9A—C9—H9B107.7
C4—C5—C6119.48 (11)O4—C10—C9108.37 (11)
C4—C5—H5120.3O4—C10—H10A110.0
C6—C5—H5120.3C9—C10—H10A110.0
C5—C6—C1119.51 (11)O4—C10—H10B110.0
C5—C6—H6120.2C9—C10—H10B110.0
C1—C6—H6120.2H10A—C10—H10B108.4
O1—C7—C8107.39 (10)C10—O4—H4108.2 (17)
O1—C7—H7A110.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.80 (3)2.10 (2)2.8808 (14)163 (2)
Symmetry code: (i) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC10H13NO4
Mr211.21
Crystal system, space groupTriclinic, 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)
V3)503.46 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.44 × 0.21 × 0.16
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008a)
Tmin, Tmax0.954, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
5772, 2924, 2224
Rint0.018
(sin θ/λ)max1)0.713
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.139, 1.06
No. of reflections2924
No. of parameters139
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O4—H4···O3i0.80 (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.

References

First citationBruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChandrasekhar, V. (2005). In Inorganic and Organometallic Polymers. Heidelberg: Springer-Verlag.
First citationChoi, E. J., Ahn, J. C., Chien, L. C., Lee, C. K., Zin, W. C., Kim, D. C. & Shin, S. T. (2004). Macromolecules, 37, 71–78.  Web of Science CrossRef CAS
First citationLiu, Z., Yu, F., Zhang, Q., Zeng, Y. & Wang, Y. (2008). Eur. Polym. J. 44, 2718–2727.  CrossRef CAS
First citationPatil, A. S., Medhi, M., Sadavarte, N. V., Wadgaonkar, P. P. & Maldar, N. N. (2010). Mater. Sci. Eng. B, 168, 111–116.  CrossRef CAS
First citationSchab-Balcerzak, E., Sek, D., Volozhin, A., Chamenko, T. & Jarzabek, B. (2002). Eur. Polym. J. 38, 423–430.  Web of Science CrossRef CAS
First citationScholl, M., Kadlecova, Z. & Klok, H.-A. (2007). Prog. Polym. Sci. 34, 24–61.  CrossRef
First citationShahram Mehdipour-Ataei, S. & Zigheimat, F. (2007). Eur. Polym. J. 43, 1020–1026.
First citationSheldrick, G. M. (2008a). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (2008b). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShockravi, A., Mehdipour-Ataei, S., Abouzari-Lotf, E. & Zakeri, M. (2007). Eur. Polym. J. 43, 620–627.  Web of Science CrossRef CAS

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