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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2012
https://doi.org/10.1107/S1600536812024865

(4-Nitro­phen­yl)methanol

Ivana Císařováa and Petr Štěpničkaa*

aDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 12840 Prague 2, Czech Republic
*Correspondence e-mail: stepnic@natur.cuni.cz

(Received 25 May 2012; accepted 31 May 2012; online 13 June 2012)

In the crystal of the title compound, C7H7NO3, mol­ecules associate into infinite chains via O—H⋯O(NO2) hydrogen bonds propagating in the [101] direction. These chains are linked via C—H⋯O(NO2) hydrogen bonds to form double-stranded ribbons lying parallel to the ac plane. The ribbons stack along the b axis by means of π–π inter­actions involving the benzene rings and the nitro group. The centroid–centroid distances of the alternating parallel aromatic rings are 3.6514 (7) and 3.8044 (7) Å.

Related literature

For the crystal structure of a ZnII complex with O-coordinated 4-nitro­benzyl alcohol, see: Koller et al. (2009[Koller, R., Stanek, K., Stolz, D., Aardoom, R., Niedermann, K. & Togni, A. (2009). Angew. Chem. Int. Ed. 48, 4332-4336.]). For a survey of typical bond lengths in organic compounds, see: Allen et al. (2006[Allen, F. H., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (2006). International Tables for Crystallography, Vol. C, ch. 9.5, pp. 790-811. Dordrecht: Kluwer Academic Publishers.]).

[Scheme 1]

Experimental

Crystal data

  • C7H7NO3

  • Mr = 153.14

  • Triclinic, [P \overline 1]

  • a = 6.2216 (5) Å

  • b = 7.4096 (6) Å

  • c = 7.7833 (6) Å

  • α = 110.867 (2)°

  • β = 93.667 (2)°

  • γ = 90.748 (3)°

  • V = 334.34 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 150 K

  • 0.53 × 0.31 × 0.28 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.939, Tmax = 0.967

  • 5239 measured reflections

  • 1442 independent reflections

  • 1269 reflections with I > 2σ(I)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.099

  • S = 1.10

  • 1442 reflections

  • 104 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1O⋯O2i 0.83 (2) 2.09 (2) 2.9095 (12) 173 (2)
C3—H3⋯O3ii 0.95 2.54 3.3799 (14) 148
Symmetry codes: (i) x-1, y, z-1; (ii) -x+3, -y, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812024865/su2438sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024865/su2438Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024865/su2438Isup3.cml

checkCIF report


Comment top

The title compound, (4-nitrophenyl)methanol [common name: 4-nitrobenzyl alcohol], is a readily available reactive organic building block, commonly used in many organic reactions. As it can separate from the reaction mixture in the form of thin crystals and thus be mistakenly taken for the desired product (D. Drahoňovský, private communication), we decided to determined its molecular structure which surprisingly was unknown. The only structurally characterized compound comprising the title alcohol reported to date is a Zn(II) complex, [ZnL2(4-O2NC6H4CH2OH)2(H2O)2](NTf2)2 [where L = 1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one and Tf = CF3SO3], isolated from the reaction mixture after zinc-catalysed trifluoromethylation of alcohols with L and Zn(NTf2)2 (Koller et al., 2009).

The molecular geometry of the title compound, Fig. 1, is rather unexceptional with bond distances falling in the usual ranges (Allen et al., 2006). The substituents in the para positions of the benzene ring bind symmetrically as indicated by the O2/O3—N1—C4 angles of 118.10 (9) ° and 119.34 (9) ° for the NO2 group and by the angles C2/C6—C1—C7 of 119.21 (10) ° and 121.32 (10) ° for the CH2OH moiety. The nitro group is rotated from the plane of the benzene ring by as little as 0.44 (13) °. On the other hand, the hydroxy group is displaced from the plane of the central ring, being rotated by the pivotal C1—C7 bond. The perpendicular distance of O1 atom from the plane of the benzene ring is 0.356 (1) Å and the torsion angle C6—C1—C7—O1 is 16.73 (16) °. A relatively small but statistically significant difference observed for the individual N—O distances [viz: N1—O2 = 1.2369 (12) Å and N1—O3 = 1.2240 (13) Å] can be accounted for by different intermolecular interactions in which the respective NO2 oxygen atoms participate.

In the crystal, molecules associate into ribbons via a combination of O—H···O and C—H···O hydrogen bonds (Fig. 2 and Table 1). The shorter O1—H1O···O2 interactions result in the formation of infinite chains from molecules related by translation in the [1 0 1] direction, whereas the soft C3—H3···O3 contacts are formed between inversion-related molecules and thus cross-link the chains with their parallel, inversion-related counterparts into infinite ribbons oriented parallel to the ac plane.

Furthermore, the molecules associate into columnar stacks oriented along the crystallographic b-axis by means of π···π interactions (Figs. 3 and 4). The interacting molecules lie across crystallographic inversion centers and are therefore exactly parallel. Mutual offset of the interacting molecules by ca. 1.4 Å (pairs A in Fig. 3) and 1.7 Å (pairs B in Fig. 3) allows for efficient interactions between the the π-systems of the benzene rings and also for interactions between the π-systems of the benzene rings and the nitro groups. Distances of the centroids of the benzene rings are 3.6514 (7) Å for molecules located around inversion centres at b/2 (pairs A) and 3.8044 (7) Å for molecules related by the inversion centres at b = 0 and 1 (pairs B). Distances of the nitrogen atom from atom C1 in pairs A and B are ca. 4.2 Å and ca. 4.4 Å, respectively.

Related literature top

For the crystal structure of a ZnII complex with O-coordinated 4-nitrobenzyl alcohol, see: Koller et al. (2009). For a survey of typical bond lengths in organic compounds, see: Allen et al. (2006).

Experimental top

Yellowish prismatic crystals suitable for X-ray diffraction analysis were selected directly from a commercial sample of the title compound (Aldrich, 99%). Attempts to recrystallize the compound from hot heptane led only to very thin, plate-like crystal aggregates, which were not suitable for -ray diffraction analysis.

Refinement top

The OH hydrogen atom was located in a difference electron density map and refined freely. The C-bound H atoms were included in calculated positions and refined as riding atoms: C-H = 0.95 and 0.97 Å for aromatic and methylene H atoms, respectively, with Uiso(H) =1.2Ueq(C).

Structure description top

The title compound, (4-nitrophenyl)methanol [common name: 4-nitrobenzyl alcohol], is a readily available reactive organic building block, commonly used in many organic reactions. As it can separate from the reaction mixture in the form of thin crystals and thus be mistakenly taken for the desired product (D. Drahoňovský, private communication), we decided to determined its molecular structure which surprisingly was unknown. The only structurally characterized compound comprising the title alcohol reported to date is a Zn(II) complex, [ZnL2(4-O2NC6H4CH2OH)2(H2O)2](NTf2)2 [where L = 1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one and Tf = CF3SO3], isolated from the reaction mixture after zinc-catalysed trifluoromethylation of alcohols with L and Zn(NTf2)2 (Koller et al., 2009).

The molecular geometry of the title compound, Fig. 1, is rather unexceptional with bond distances falling in the usual ranges (Allen et al., 2006). The substituents in the para positions of the benzene ring bind symmetrically as indicated by the O2/O3—N1—C4 angles of 118.10 (9) ° and 119.34 (9) ° for the NO2 group and by the angles C2/C6—C1—C7 of 119.21 (10) ° and 121.32 (10) ° for the CH2OH moiety. The nitro group is rotated from the plane of the benzene ring by as little as 0.44 (13) °. On the other hand, the hydroxy group is displaced from the plane of the central ring, being rotated by the pivotal C1—C7 bond. The perpendicular distance of O1 atom from the plane of the benzene ring is 0.356 (1) Å and the torsion angle C6—C1—C7—O1 is 16.73 (16) °. A relatively small but statistically significant difference observed for the individual N—O distances [viz: N1—O2 = 1.2369 (12) Å and N1—O3 = 1.2240 (13) Å] can be accounted for by different intermolecular interactions in which the respective NO2 oxygen atoms participate.

In the crystal, molecules associate into ribbons via a combination of O—H···O and C—H···O hydrogen bonds (Fig. 2 and Table 1). The shorter O1—H1O···O2 interactions result in the formation of infinite chains from molecules related by translation in the [1 0 1] direction, whereas the soft C3—H3···O3 contacts are formed between inversion-related molecules and thus cross-link the chains with their parallel, inversion-related counterparts into infinite ribbons oriented parallel to the ac plane.

Furthermore, the molecules associate into columnar stacks oriented along the crystallographic b-axis by means of π···π interactions (Figs. 3 and 4). The interacting molecules lie across crystallographic inversion centers and are therefore exactly parallel. Mutual offset of the interacting molecules by ca. 1.4 Å (pairs A in Fig. 3) and 1.7 Å (pairs B in Fig. 3) allows for efficient interactions between the the π-systems of the benzene rings and also for interactions between the π-systems of the benzene rings and the nitro groups. Distances of the centroids of the benzene rings are 3.6514 (7) Å for molecules located around inversion centres at b/2 (pairs A) and 3.8044 (7) Å for molecules related by the inversion centres at b = 0 and 1 (pairs B). Distances of the nitrogen atom from atom C1 in pairs A and B are ca. 4.2 Å and ca. 4.4 Å, respectively.

For the crystal structure of a ZnII complex with O-coordinated 4-nitrobenzyl alcohol, see: Koller et al. (2009). For a survey of typical bond lengths in organic compounds, see: Allen et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, showing the atom-labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A section of H-bonded ribbons in the structure of the title compound. Hydrogen bonds are indicated with dashed lines.
[Figure 3] Fig. 3. A view along the a axis of the π···π stacking interactions of individual molecules in the structure of the title compound.
[Figure 4] Fig. 4. A view along the a axis of the crystal packing of the title compound, highlighting the interplay of hydrogen bonding (see Table 1) and π···π interactions [The yellow box limits the section presented in Fig. 3].
(4-nitrophenyl)methanol top
Crystal data top
C7H7NO3Z = 2
Mr = 153.14F(000) = 160
Triclinic, P1Dx = 1.521 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2216 (5) ÅCell parameters from 3056 reflections
b = 7.4096 (6) Åθ = 2.9–27.0°
c = 7.7833 (6) ŵ = 0.12 mm−1
α = 110.867 (2)°T = 150 K
β = 93.667 (2)°Prism, colorless
γ = 90.748 (3)°0.53 × 0.31 × 0.28 mm
V = 334.34 (5) Å3
Data collection top
Bruker APEXII CCD
diffractometer		1442 independent reflections
Radiation source: fine-focus sealed tube1269 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −7→7
Tmin = 0.939, Tmax = 0.967k = −9→9
5239 measured reflectionsl = −9→9
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0549P)2 + 0.0737P]
where P = (Fo2 + 2Fc2)/3
1442 reflections(Δ/σ)max < 0.001
104 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C7H7NO3γ = 90.748 (3)°
Mr = 153.14V = 334.34 (5) Å3
Triclinic, P1Z = 2
a = 6.2216 (5) ÅMo Kα radiation
b = 7.4096 (6) ŵ = 0.12 mm−1
c = 7.7833 (6) ÅT = 150 K
α = 110.867 (2)°0.53 × 0.31 × 0.28 mm
β = 93.667 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		1442 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1269 reflections with I > 2σ(I)
Tmin = 0.939, Tmax = 0.967Rint = 0.016
5239 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.25 e Å−3
1442 reflectionsΔρmin = −0.29 e Å−3
104 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 diffractions. 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
O10.55157 (14)0.37365 (14)0.71166 (12)0.0289 (2)
H1O0.459 (3)0.352 (3)0.625 (3)0.059 (6)*
O21.19725 (14)0.31301 (14)1.43192 (11)0.0291 (2)
O31.44094 (13)0.17141 (12)1.25026 (12)0.0260 (2)
N11.26402 (15)0.24252 (13)1.27641 (13)0.0185 (2)
C10.86002 (18)0.24567 (15)0.82183 (15)0.0164 (2)
C21.06259 (18)0.16628 (15)0.79623 (15)0.0187 (3)
H21.10930.11300.67510.022*
C31.19706 (17)0.16352 (15)0.94381 (15)0.0177 (3)
H31.33480.10880.92600.021*
C41.12356 (17)0.24351 (14)1.11879 (14)0.0158 (2)
C50.92362 (18)0.32390 (15)1.14985 (15)0.0173 (2)
H50.87810.37761.27140.021*
C60.79120 (17)0.32436 (15)0.99981 (15)0.0172 (2)
H60.65310.37841.01820.021*
C70.71876 (19)0.24303 (16)0.65630 (15)0.0215 (3)
H7A0.80640.27920.57100.026*
H7B0.65620.11090.59010.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0235 (5)0.0379 (5)0.0213 (4)0.0103 (4)−0.0055 (3)0.0068 (4)
O20.0257 (5)0.0455 (6)0.0151 (4)0.0062 (4)0.0000 (3)0.0098 (4)
O30.0197 (4)0.0303 (5)0.0278 (5)0.0086 (3)−0.0016 (3)0.0103 (4)
N10.0176 (5)0.0194 (5)0.0191 (5)0.0006 (3)−0.0008 (4)0.0081 (4)
C10.0184 (5)0.0137 (5)0.0171 (5)−0.0021 (4)−0.0014 (4)0.0060 (4)
C20.0217 (6)0.0175 (5)0.0155 (5)0.0010 (4)0.0034 (4)0.0041 (4)
C30.0160 (5)0.0162 (5)0.0209 (6)0.0024 (4)0.0028 (4)0.0062 (4)
C40.0161 (5)0.0145 (5)0.0172 (5)−0.0011 (4)−0.0020 (4)0.0066 (4)
C50.0180 (5)0.0185 (5)0.0154 (5)0.0007 (4)0.0022 (4)0.0058 (4)
C60.0146 (5)0.0171 (5)0.0201 (5)0.0015 (4)0.0010 (4)0.0071 (4)
C70.0225 (6)0.0235 (6)0.0173 (5)0.0031 (4)−0.0015 (4)0.0063 (4)
Geometric parameters (Å, º) top
O1—C71.4110 (13)C2—H20.9500
O1—H1O0.82 (2)C3—C41.3881 (15)
O2—N11.2369 (12)C3—H30.9500
O3—N11.2239 (12)C4—C51.3842 (15)
N1—C41.4623 (13)C5—C61.3865 (15)
C1—C21.3936 (15)C5—H50.9500
C1—C61.3961 (15)C6—H60.9500
C1—C71.5065 (14)C7—H7A0.9900
C2—C31.3835 (15)C7—H7B0.9900
C7—O1—H1O109.2 (14)C5—C4—N1118.87 (10)
O3—N1—O2122.56 (9)C3—C4—N1118.37 (10)
O3—N1—C4119.34 (9)C4—C5—C6118.59 (10)
O2—N1—C4118.10 (9)C4—C5—H5120.7
C2—C1—C6119.46 (10)C6—C5—H5120.7
C2—C1—C7119.21 (10)C5—C6—C1120.24 (10)
C6—C1—C7121.32 (10)C5—C6—H6119.9
C3—C2—C1121.30 (10)C1—C6—H6119.9
C3—C2—H2119.3O1—C7—C1110.28 (9)
C1—C2—H2119.3O1—C7—H7A109.6
C2—C3—C4117.65 (10)C1—C7—H7A109.6
C2—C3—H3121.2O1—C7—H7B109.6
C4—C3—H3121.2C1—C7—H7B109.6
C5—C4—C3122.76 (10)H7A—C7—H7B108.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.83 (2)2.09 (2)2.9095 (12)173 (2)
C3—H3···O3ii0.952.543.3799 (14)148
Symmetry codes: (i) x−1, y, z−1; (ii) −x+3, −y, −z+2.

Experimental details

Crystal data
Chemical formulaC7H7NO3
Mr153.14
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)6.2216 (5), 7.4096 (6), 7.7833 (6)
α, β, γ (°)110.867 (2), 93.667 (2), 90.748 (3)
V (Å3)334.34 (5)
Z2
Radiation typeMo Kα
µ (mm−1)0.12
Crystal size (mm)0.53 × 0.31 × 0.28
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.939, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections		5239, 1442, 1269
Rint0.016
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.099, 1.10
No. of reflections1442
No. of parameters104
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.25, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.83 (2)2.09 (2)2.9095 (12)173 (2)
C3—H3···O3ii0.952.543.3799 (14)148
Symmetry codes: (i) x−1, y, z−1; (ii) −x+3, −y, −z+2.
 

Acknowledgements

Financial support from the Ministry of Education of the Czech Republic (project No. MSM0021620857) is gratefully acknowledged.

References

First citationAllen, F. H., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (2006). International Tables for Crystallography, Vol. C, ch. 9.5, pp. 790–811. Dordrecht: Kluwer Academic Publishers.  Google Scholar
 First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationKoller, R., Stanek, K., Stolz, D., Aardoom, R., Niedermann, K. & Togni, A. (2009). Angew. Chem. Int. Ed. 48, 4332–4336.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2012
https://doi.org/10.1107/S1600536812024865
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