2 Naphthalenol

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organic papers

o52

Bernard Marciniaket al. C₁₀H₈O DOI: 10.1107/S1600536802022808 Acta Cryst.(2003). E59, o52±o53 Acta Crystallographica Section E

Structure Reports

Online

ISSN 1600-5368

2-Naphthalenol

Bernard Marciniak,*

Ewa Rozycka-Sokolowska and Volodymyr Pavlyuk

Institute of Chemistry and Environment Protec-tion, Pedagogical University of Czestochowa, al. Armii Krajowej 13/15, 42-200 Czestochowa, Poland

Correspondence e-mail: [email protected]

Key indicators Single-crystal X-ray study T= 293 K

Mean(C±C) = 0.006 AÊ Rfactor = 0.045 wRfactor = 0.093 Data-to-parameter ratio = 8.5

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

In the solid state, the non-centrosymmetric structure of the title compound, C10H8O, is stabilized both by van der Waals interactions and by OÐH O intermolecular hydrogen bonds. These hydrogen bonds link every molecule with two neighbouring non-equivalent molecules, forming chains. The asymmetric unit contains two molecules, which are related to each other by a pseudo-inversion centre.

Comment

Because of potentially high non-linearities and a rapid response in electro-optic effects that often far surpasses those of inorganic non-linear optical (NLO) materials, some polar organic crystals which form non-centrosymmetric crystal structures are of much current interest (Babu et al., 2002; Perumalet al., 2002; Vijayanet al., 2002; Tsunesadaet al., 2002; Rajendranet al., 2001; Palet al., 2002). Although such prop-erties have not been con®rmed experimentally in the case of 2-naphthalenol, (I), the previous crystal structure analysis of this compound, performed with the aid of optical transforms (Watson & Hargreaves, 1958), showed that it crystallizes in the monoclinic non-centrosymmetric space group Ia, with a = 8.185 AÊ,b= 5.950 AÊ,c= 36.29 AÊ and = 119.52_{. This}

indi-cates that the polar 2-naphthalenol crystals may be treated as a potential organic NLO material. The non-centrosymmetric crystal structure of this compound was, however, only partially solved by two-dimensional Fourier calculations, using X-ray photographic data. New single-crystal X-ray diffraction data obtained by us fully con®rm that the structure of (I) is non-centrosymmetric, although we have used the alternative space group settingCc, because of the smallerangle this entails.

The unit cell of (I) contains eight molecules, occupying two non-equivalent sets of general positions. Sets of equivalent molecules stack in sheets perpendicular to theaaxis, and each of these molecules is linked to two neighbouring non-equivalent molecules through OÐH O intermolecular hydrogen bonds (see Table 1 for details). The two molecules in the asymmetric unit are related to each other by pseudo-inversion symmetry.

A metastable modi®cation of this compound, which is isomorphous with naphthalene, has been reported by Coppens & Heair®eld (1965).

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Experimental

As a starting material we used analytically pure, commercially available 2-naphthalenol (POCH, Poland), in which ®ve major impurities (1,10_{-bi-2-naphthol, oleic acid amide, methylnaphthol,} 5(12H)-naphthacenone and binaphthacenone) were detected and identi®ed using gas chromatography. Analyses were performed on a Hewlett Packard 6890 GC System gas chromatograph with an FID detector (fused silica capillary column of dimensions 300.32 mm I. D.; an HP1 methyl silicone stationary phase; cool on column type injector; helium as a carrier gas). For the identi®cation of these impurities, we also used a Hewlett Packard 5890 series II gas chro-matograph equipped with MS detection, which operated under nearly the same conditions. The GC±FID analysis of a chloroform-extracted sample prepared from the commercial 2-naphthalenol has shown that its total purity is 99.49%. To remove the detected impurities, the starting material was pre-puri®ed by twofold crystallization from anhydrous ethanol, and then two-stage zone puri®cation was performed with the help of a multistage zone re®ner (100 passages of the molten zone with a rate of 10 mm hÿ1_{in the ®rst, and 5 mm h}ÿ1_in the second stage; spectrally pure nitrogen as an inert gas). The total impurity content in the material collected from the central and upper parts of the zone-melted ingots was <0.001% by mass. Single crystals were grown from a nucleated spontaneously supercooled solution in chloroform at a constant temperature of 307 K, in an apparatus described previously by Marciniak (2002).

Crystal data

C10H8O

Mr= 144.16

Monoclinic,Cc a= 32.074 (6) AÊ

b= 5.931 (1) AÊ

c= 8.127 (2) AÊ

= 101.18 (3)

V= 1516.7 (5) AÊ3

Z= 8

Dx= 1.263 Mg mÿ3

MoKradiation Cell parameters from 30

re¯ections

= 1.2±28.0

= 0.08 mmÿ1

T= 293 (2) K Needle, pale yellow 0.400.060.03 mm

Data collection

DARCH-1 diffractometer

!±2scans

Absorption correction: re®ned fromF(DIFABS; Walker & Stuart, 1983)

Tmin= 0.958,Tmax= 0.998

1875 measured re¯ections 1744 independent re¯ections 1339 re¯ections withI> 2(I)

Rint= 0.020

max= 27.5

h=ÿ41!40

k=ÿ7!7

l= 0!10

3 standard re¯ections frequency: 120 min intensity decay: 5%

Re®nement

Re®nement onF2

R[F2_{> 2}₍_F2_{)] = 0.045}

wR(F2_{) = 0.093}

S= 1.30 1744 re¯ections 204 parameters

H-atom parameters constrained

w= 1/[2₍_F

o2) + (0.0121P)2]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.007 max= 0.09 e AÊÿ3 min=ÿ0.14 e AÊÿ3

Table 1

Hydrogen-bonding geometry (AÊ,_).

DÐH A DÐH H A D A DÐH A

O1ÐH1 O2i _0.82 _2.14 _{2.764 (3)} ₁₃₃

O2ÐH2A O1ii _0.82 _2.45 _{2.752 (3)} ₁₀₃ Symmetry codes: (i)x;1y;z; (ii)x;1ÿy;1

2z.

H atoms were constrained with a riding model, including torsional freedom of OH groups.

Data collection: DARCH package (Burevestnik, 1991); cell re®nement: DARCH package; data reduction: DARCH package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP-3 (Farrugia, 1997) andPLATON(Spek, 2003); software used to prepare material for publication:

SHELXL97.

We are grateful to Dr V. Davydov for the data collection.

References

Babu, R. R, Vijayan, N., Copalakrishnan, R. & Ramasamy, P. (2002).J. Cryst. Growth,240, 545±548.

Burevestnik (1991). DARCH package. NPO Burevestnik, St. Petersburg, Russia.

Coppens, P. & Heair®eld, I. (1965).Isr. J. Chem.3, 26±28. Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.

Marciniak, B. (2002).J. Cryst. Growth,236, 333±344.

Pal, T., Kar, T., Wang, X.-Q., Zhou, G.-Y., Wang. D., Cheng, X.-F. & Yang, Z.-H. (2002).J. Cryst. Growth,235, 523±528.

Perumal, C. K. L., Arulchakkaravarthi, A., Santhanaraghavan, P. & Ramasamy, P. (2002).J. Cryst. Growth,241, 200±2005.

Rajendran, K. V., Jayaraman, D., Jayavel, R., Kumar, R. M. & Ramasamy, P. (2001).J. Cryst. Growth,224, 122±127.

Sheldrick, G. M. (1990).Acta Cryst.A46, 467±473.

Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Spek, A. L. (2003).J. Appl. Cryst.36, 7±13.

Tsunesada, F., Iwai, T., Watanabe, T., Adach, H., Yoshimura, M., Mori, Y. & Sasaki, T. (2002).J. Cryst. Growth,237±239, 2104±2106.

Vijayan, N., Babu, R. R., Gopalakrishnan, R., Dhanuskodi, S. & Ramasamy, P. (2002).J. Cryst. Growth,236, 407±412.

Walker, N. & Stuart, D. (1983).Acta Cryst.A39, 158±166. Watson, H. C. & Hargreaves, A. (1958).Acta Cryst.11, 556±562.

Figure 2

The crystal packing, viewed along thebaxis.

Figure 1

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supporting information

sup-1 Acta Cryst. (2003). E59, o52–o53

supporting information

Acta Cryst. (2003). E59, o52–o53 [https://doi.org/10.1107/S1600536802022808]

2-Naphthalenol

Bernard Marciniak, Ewa Rozycka-Sokolowska and Volodymyr Pavlyuk

(I)

Crystal data

C10H8O

Mr = 144.16 Monoclinic, Cc a = 32.074 (6) Å

b = 5.931 (1) Å

c = 8.127 (2) Å

β = 101.18 (3)°

V = 1516.7 (5) Å3

Z = 8

F(000) = 608

Dx = 1.263 Mg m−3

Melting point: 123 K

Mo Kα radiation, λ = 0.71069 Å Cell parameters from 30 reflections

θ = 1.2–28.0°

µ = 0.08 mm−1

T = 293 K

Needle, pale yellow 0.4 × 0.06 × 0.03 mm

Data collection

DARCH-1 diffractometer

Radiation source: BSW x-ray tube Graphite monochromator

ω–2θ scans

Absorption correction: part of the refinement model (ΔF)

(DIFABS; Walker & Stuart, 1983)

Tmin = 0.958, Tmax = 0.998

1875 measured reflections

1744 independent reflections 1339 reflections with I > 2σ(I)

Rint = 0.020

θmax = 27.5°, θmin = 1.3°

h = −41→40

k = −7→7

l = 0→10

3 standard reflections every 120 min intensity decay: 5%

Refinement

Refinement on F2

Least-squares matrix: full

R[F2_{> 2}_σ₍_F2_{)] = 0.045}

wR(F2_{) = 0.093}

S = 1.30 1744 reflections 204 parameters 2 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2₍_F

o2) + (0.0121P)2]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.007

Δρmax = 0.09 e Å−3

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Special details

Experimental. The DIFABS only insignificantly reduced the R value, but it enabled us much better refinement of the structure parameters.

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₎

x y z Uiso*/Ueq

O1 0.26010 (9) 0.8581 (4) 0.2004 (4) 0.0870 (7)

H1 0.2586 0.9954 0.2096 0.130*

C1 0.30146 (14) 0.7886 (7) 0.2607 (6) 0.0869 (12) C2 0.32747 (14) 0.9230 (8) 0.3703 (6) 0.0888 (12)

H2 0.3175 1.0611 0.4005 0.107*

C3 0.36958 (15) 0.8568 (7) 0.4395 (6) 0.0888 (12) C4 0.39776 (12) 0.9928 (7) 0.5500 (6) 0.0856 (11)

H4 0.3890 1.1339 0.5799 0.103*

C5 0.43793 (15) 0.9203 (7) 0.6142 (6) 0.0896 (11)

H5 0.4554 1.0069 0.6948 0.108*

C6 0.45332 (14) 0.7177 (6) 0.5610 (5) 0.0798 (10)

H6 0.4816 0.6756 0.5966 0.096*

C7 0.42577 (15) 0.5842 (8) 0.4556 (6) 0.0958 (13)

H7 0.4354 0.4440 0.4276 0.115*

C8 0.38384 (14) 0.6449 (7) 0.3867 (5) 0.0857 (11) C9 0.35595 (17) 0.5133 (9) 0.2751 (7) 0.1030 (14)

H9 0.3651 0.3745 0.2423 0.124*

C10 0.31602 (16) 0.5807 (8) 0.2130 (6) 0.0987 (14)

H10 0.2980 0.4889 0.1381 0.118*

O2 0.22878 (9) 0.2095 (4) 0.3642 (4) 0.0905 (8)

H2A 0.2386 0.3156 0.4240 0.136*

C11 0.18700 (12) 0.2519 (6) 0.2957 (5) 0.0748 (10) C12 0.16206 (13) 0.1045 (6) 0.1936 (5) 0.0825 (10)

H12 0.1737 −0.0316 0.1676 0.099*

C13 0.11971 (13) 0.1504 (6) 0.1265 (5) 0.0785 (10) C14 0.09277 (14) 0.0033 (7) 0.0178 (6) 0.0918 (12)

H14 0.1035 −0.1333 −0.0119 0.110*

C15 0.05175 (15) 0.0564 (7) −0.0441 (6) 0.0911 (12)

H15 0.0346 −0.0455 −0.1133 0.109*

C16 0.03480 (15) 0.2636 (7) −0.0053 (6) 0.0869 (11)

H16 0.0070 0.3033 −0.0531 0.104*

C17 0.05940 (13) 0.4037 (7) 0.1023 (6) 0.0841 (11)

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supporting information

C18 0.10132 (14) 0.3564 (7) 0.1697 (5) 0.0853 (11) C19 0.12873 (16) 0.5065 (8) 0.2786 (7) 0.1074 (15)

H19 0.1181 0.6439 0.3071 0.129*

C20 0.16999 (15) 0.4536 (8) 0.3416 (6) 0.1001 (14)

H20 0.1869 0.5518 0.4153 0.120*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

O1 0.0912 (17) 0.0816 (14) 0.0892 (18) 0.0035 (13) 0.0202 (14) 0.0036 (15) C1 0.093 (3) 0.079 (2) 0.090 (3) 0.006 (2) 0.020 (2) 0.003 (2) C2 0.088 (3) 0.084 (2) 0.097 (3) 0.0010 (19) 0.023 (2) −0.004 (2) C3 0.095 (3) 0.085 (2) 0.086 (3) 0.003 (2) 0.017 (3) 0.003 (2) C4 0.084 (3) 0.085 (2) 0.087 (3) 0.004 (2) 0.016 (2) −0.001 (2) C5 0.089 (3) 0.092 (3) 0.087 (3) −0.002 (2) 0.014 (2) 0.000 (2) C6 0.076 (2) 0.082 (2) 0.081 (3) 0.0029 (19) 0.014 (2) −0.001 (2) C7 0.102 (3) 0.089 (3) 0.100 (3) 0.001 (2) 0.027 (3) −0.001 (2) C8 0.082 (3) 0.086 (2) 0.090 (3) 0.002 (2) 0.018 (2) 0.000 (2) C9 0.112 (3) 0.101 (3) 0.100 (4) 0.000 (3) 0.030 (3) −0.002 (3) C10 0.102 (4) 0.094 (3) 0.100 (4) −0.004 (2) 0.020 (3) −0.002 (2) O2 0.0917 (18) 0.0925 (16) 0.0863 (19) 0.0019 (14) 0.0147 (15) 0.0009 (14) C11 0.071 (2) 0.0766 (19) 0.076 (3) −0.0046 (16) 0.0133 (19) −0.0009 (18) C12 0.085 (3) 0.082 (2) 0.081 (3) 0.0027 (19) 0.017 (2) 0.0001 (19) C13 0.073 (2) 0.0795 (19) 0.083 (3) 0.0014 (17) 0.014 (2) 0.0001 (19) C14 0.099 (3) 0.088 (2) 0.089 (3) 0.007 (2) 0.021 (3) 0.001 (2) C15 0.093 (3) 0.091 (3) 0.090 (3) 0.001 (2) 0.017 (2) −0.003 (2) C16 0.087 (3) 0.086 (2) 0.088 (3) −0.001 (2) 0.017 (2) 0.002 (2) C17 0.079 (2) 0.088 (2) 0.085 (3) 0.0020 (19) 0.016 (2) −0.002 (2) C18 0.091 (3) 0.084 (2) 0.080 (3) 0.000 (2) 0.015 (2) 0.003 (2) C19 0.104 (3) 0.108 (3) 0.107 (4) −0.002 (3) 0.014 (3) −0.007 (3) C20 0.098 (3) 0.109 (3) 0.092 (3) 0.002 (2) 0.016 (3) −0.001 (2)

Geometric parameters (Å, º)

O1—C1 1.385 (5) O2—C11 1.371 (5)

O1—H1 0.820 O2—H2A 0.820

C1—C2 1.355 (6) C11—C12 1.355 (5)

C1—C10 1.400 (6) C11—C20 1.395 (6)

C2—C3 1.414 (6) C12—C13 1.389 (6)

C2—H2 0.930 C12—H12 0.930

C3—C4 1.400 (6) C13—C14 1.411 (6)

C3—C8 1.432 (5) C13—C18 1.430 (5)

C4—C5 1.362 (6) C14—C15 1.351 (6)

C4—H4 0.930 C14—H14 0.930

C5—C6 1.399 (6) C15—C16 1.405 (6)

C5—H5 0.930 C15—H15 0.930

C6—C7 1.359 (6) C16—C17 1.345 (6)

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C7—C8 1.400 (7) C17—C18 1.379 (6)

C7—H7 0.930 C17—H17 0.930

C8—C9 1.385 (7) C18—C19 1.431 (6)

C9—C10 1.343 (7) C19—C20 1.360 (6)

C9—H9 0.930 C19—H19 0.930

C10—H10 0.930 C20—H20 0.930

C1—O1—H1 109.5 C11—O2—H2A 109.5

C2—C1—O1 118.9 (4) C12—C11—O2 123.0 (3)

C2—C1—C10 120.3 (4) C12—C11—C20 120.1 (4)

O1—C1—C10 120.8 (4) O2—C11—C20 116.8 (3)

C1—C2—C3 121.1 (4) C11—C12—C13 122.0 (4)

C1—C2—H2 119.4 C11—C12—H12 119.0

C3—C2—H2 119.4 C13—C12—H12 119.0

C4—C3—C2 122.9 (4) C12—C13—C14 123.9 (4)

C4—C3—C8 119.6 (4) C12—C13—C18 119.3 (4)

C2—C3—C8 117.4 (4) C14—C13—C18 116.7 (4)

C5—C4—C3 120.6 (4) C15—C14—C13 121.5 (4)

C5—C4—H4 119.7 C15—C14—H14 119.2

C3—C4—H4 119.7 C13—C14—H14 119.2

C4—C5—C6 121.1 (4) C14—C15—C16 120.8 (4)

C4—C5—H5 119.4 C14—C15—H15 119.6

C6—C5—H5 119.4 C16—C15—H15 119.6

C7—C6—C5 118.0 (4) C17—C16—C15 118.9 (5)

C7—C6—H6 121.0 C17—C16—H16 120.6

C5—C6—H6 121.0 C15—C16—H16 120.6

C6—C7—C8 124.0 (4) C16—C17—C18 122.4 (4)

C6—C7—H7 118.0 C16—C17—H17 118.8

C8—C7—H7 118.0 C18—C17—H17 118.8

C9—C8—C7 124.4 (4) C17—C18—C13 119.6 (4)

C9—C8—C3 119.2 (4) C17—C18—C19 123.6 (4)

C7—C8—C3 116.4 (4) C13—C18—C19 116.8 (4)

C10—C9—C8 121.7 (5) C20—C19—C18 121.7 (5)

C10—C9—H9 119.1 C20—C19—H19 119.2

C8—C9—H9 119.1 C18—C19—H19 119.2

C9—C10—C1 120.2 (5) C19—C20—C11 120.0 (5)

C9—C10—H10 119.9 C19—C20—H20 120.0

C1—C10—H10 119.9 C11—C20—H20 120.0

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supporting information

C6—C7—C8—C9 177.8 (5) C16—C17—C18—C13 −0.7 (7) C6—C7—C8—C3 −3.1 (7) C16—C17—C18—C19 177.2 (5) C4—C3—C8—C9 −178.9 (5) C12—C13—C18—C17 179.4 (4) C2—C3—C8—C9 −1.5 (6) C14—C13—C18—C17 −1.3 (6) C4—C3—C8—C7 2.0 (6) C12—C13—C18—C19 1.3 (6) C2—C3—C8—C7 179.4 (4) C14—C13—C18—C19 −179.4 (4) C7—C8—C9—C10 −179.9 (5) C17—C18—C19—C20 −179.6 (5) C3—C8—C9—C10 1.0 (8) C13—C18—C19—C20 −1.6 (7) C8—C9—C10—C1 −0.1 (8) C18—C19—C20—C11 2.2 (8) C2—C1—C10—C9 −0.3 (8) C12—C11—C20—C19 −2.6 (7) O1—C1—C10—C9 −178.6 (4) O2—C11—C20—C19 −179.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

O1—H1···O2i _0.82 _2.14 _{2.764 (3)} ₁₃₃

O2—H2A···O1ii _0.82 _2.45 _{2.752 (3)} ₁₀₃