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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o380.
Published online 2010 January 16. doi:  10.1107/S1600536810000383
PMCID: PMC2979784

2-[2-(Hydroxy­meth­yl)phen­yl]-1-(1-naphth­yl)ethanol

Abstract

The mol­ecular conformation of the title compound, C19H18O2, is stabilized by an intra­molecular O—H—O hydrogen bond. In addition, inter­molecular O—H—O inter­actions link the mol­ecules into zigzag chains running along the c axis.

Related literature

For related structures, see: Gałdecki et al. (1984 [triangle]); Hoyos-Guerrero et al. (1983 [triangle]); Manivel et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o380-scheme1.jpg

Experimental

Crystal data

  • C19H18O2
  • M r = 278.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o380-efi1.jpg
  • a = 16.207 (4) Å
  • b = 12.820 (3) Å
  • c = 7.7888 (18) Å
  • β = 111.172 (3)°
  • V = 1509.2 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 290 K
  • 0.60 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.943, T max = 0.992
  • 5447 measured reflections
  • 1447 independent reflections
  • 1216 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.085
  • S = 1.07
  • 1447 reflections
  • 198 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and CAMERON (Watkin et al., 1993 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000383/bt5147sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000383/bt5147Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

The molecular conformation of the title compound is stabilized by an intramolecular O—H—O hydrogen bond. In addition, intermolecular O—H—O interactions link the molecules to zigzag chains running along the c axis.

Experimental

3-(naphthalen-1-yl)isocoumarin (1 eq.) was dissolved in 10 volumes of methanol, sodium borohydride (4 eq.) was added to it and stirred at 50° C under nitrogen atmosphere for 4 hrs. Then two more equivalents of NaBH4 was further added and left overnight at 50° C for completion of the reaction. After TLC analysis, solvent methanol was removed, extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried with anhydrous Na2SO4, evaporated to yield the title compound, which was further purified by washing with petroleum ether. Single-crystals for the structure analysis were obtained by slow evaporation of the ethanol solution.

Refinement

In the absence of anomalous scatterers, 1191 Friedel pairs were merged and the absolute configuration was arbitrarily set. All H atoms were located from difference fourier maps Those bonded to C were positioned geometrically and refined using a riding model with C—H bond lengths of 0.93 Å and 0.97 Å for aromatic and for methylene H atoms, respectively, and Uiso(H) = 1.2Ueq(C). The hydroxyl H atoms were freely refined.

Figures

Fig. 1.
ORTEP diagram of the title compound with 50% probability displacement ellipsoids.
Fig. 2.
The crystal packing diagram. The dotted lines indicate intermolecular O—H···O hydrogen bonds.

Crystal data

C19H18O2F(000) = 592
Mr = 278.33Dx = 1.225 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2097 reflections
a = 16.207 (4) Åθ = 2.7–26.3°
b = 12.820 (3) ŵ = 0.08 mm1
c = 7.7888 (18) ÅT = 290 K
β = 111.172 (3)°Needle, colorless
V = 1509.2 (6) Å30.60 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1447 independent reflections
Radiation source: fine-focus sealed tube1216 reflections with I > 2σ(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 25.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −19→19
Tmin = 0.943, Tmax = 0.992k = −15→15
5447 measured reflectionsl = −9→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0524P)2] where P = (Fo2 + 2Fc2)/3
1447 reflections(Δ/σ)max < 0.001
198 parametersΔρmax = 0.15 e Å3
2 restraintsΔρmin = −0.14 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)

xyzUiso*/Ueq
O10.07843 (13)0.13119 (13)0.4503 (3)0.0541 (5)
H1O0.074 (2)0.091 (3)0.357 (6)0.100 (13)*
O20.05537 (13)0.04804 (13)0.7513 (3)0.0541 (5)
H2O0.068 (3)0.070 (3)0.647 (6)0.112 (14)*
C10.12467 (16)0.27456 (16)0.2976 (3)0.0391 (5)
C20.03809 (18)0.2984 (2)0.2052 (4)0.0513 (6)
H2−0.00520.26690.23990.062*
C30.0124 (2)0.3708 (2)0.0562 (4)0.0633 (8)
H3−0.04720.3859−0.00560.076*
C40.0748 (2)0.4177 (2)0.0047 (4)0.0609 (8)
H40.05750.4648−0.09260.073*
C50.2323 (3)0.4454 (2)0.0452 (4)0.0681 (9)
H50.21570.4922−0.05270.082*
C60.3193 (3)0.4256 (2)0.1359 (5)0.0760 (9)
H60.36170.45970.10200.091*
C70.3451 (2)0.3536 (2)0.2810 (5)0.0672 (8)
H70.40490.33930.34190.081*
C80.28404 (18)0.30420 (19)0.3341 (4)0.0514 (7)
H80.30290.25660.43050.062*
C90.19190 (16)0.32361 (16)0.2457 (3)0.0405 (5)
C100.16515 (18)0.39629 (17)0.0958 (3)0.0476 (6)
C110.15080 (17)0.19895 (15)0.4609 (3)0.0414 (5)
H110.20070.15630.45910.050*
C120.17832 (17)0.25725 (16)0.6467 (3)0.0445 (6)
H12A0.21150.31910.64000.053*
H12B0.12540.27990.66680.053*
C130.23412 (17)0.19156 (17)0.8103 (3)0.0415 (5)
C140.32550 (19)0.1898 (2)0.8541 (4)0.0556 (7)
H140.35000.23200.78770.067*
C150.3809 (2)0.1274 (2)0.9933 (4)0.0640 (8)
H150.44150.12701.01840.077*
C160.3454 (2)0.0655 (2)1.0947 (4)0.0625 (8)
H160.38180.02231.18680.075*
C170.2558 (2)0.06847 (18)1.0582 (3)0.0551 (7)
H170.23250.02831.12920.066*
C180.19887 (17)0.13022 (15)0.9173 (3)0.0430 (6)
C190.1015 (2)0.1264 (2)0.8835 (4)0.0537 (7)
H19A0.09360.11230.99900.064*
H19B0.07560.19400.83990.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0811 (13)0.0413 (9)0.0459 (10)−0.0112 (9)0.0300 (9)−0.0034 (8)
O20.0705 (11)0.0446 (9)0.0504 (10)−0.0041 (8)0.0259 (9)0.0052 (8)
C10.0571 (15)0.0258 (10)0.0338 (12)0.0073 (10)0.0156 (11)−0.0023 (10)
C20.0587 (17)0.0462 (14)0.0491 (15)0.0068 (12)0.0194 (13)−0.0007 (12)
C30.0707 (18)0.0563 (16)0.0486 (16)0.0238 (15)0.0042 (14)0.0046 (14)
C40.093 (2)0.0376 (13)0.0428 (15)0.0156 (15)0.0134 (15)0.0089 (12)
C50.119 (3)0.0344 (14)0.0600 (18)−0.0026 (16)0.0431 (19)0.0079 (13)
C60.098 (3)0.0610 (19)0.084 (2)−0.0149 (18)0.051 (2)0.0039 (18)
C70.0674 (19)0.0587 (18)0.081 (2)−0.0007 (14)0.0338 (17)0.0029 (16)
C80.0678 (18)0.0395 (13)0.0498 (16)0.0080 (12)0.0248 (14)0.0057 (12)
C90.0617 (16)0.0258 (10)0.0339 (12)0.0059 (10)0.0172 (11)−0.0024 (9)
C100.0792 (19)0.0254 (10)0.0388 (14)0.0043 (11)0.0220 (14)−0.0010 (10)
C110.0572 (14)0.0286 (10)0.0410 (13)0.0049 (11)0.0210 (11)0.0027 (10)
C120.0638 (17)0.0292 (11)0.0421 (13)−0.0002 (11)0.0211 (12)0.0019 (10)
C130.0595 (17)0.0294 (11)0.0350 (12)−0.0003 (10)0.0162 (11)−0.0034 (9)
C140.0640 (19)0.0554 (16)0.0471 (15)−0.0051 (14)0.0197 (13)−0.0004 (13)
C150.0588 (17)0.0668 (18)0.0540 (18)0.0036 (14)0.0055 (14)−0.0052 (15)
C160.083 (2)0.0468 (15)0.0401 (15)0.0099 (14)0.0012 (14)0.0023 (12)
C170.091 (2)0.0349 (13)0.0390 (14)−0.0010 (13)0.0228 (14)−0.0008 (11)
C180.0658 (17)0.0276 (10)0.0372 (13)0.0008 (10)0.0205 (12)−0.0053 (10)
C190.078 (2)0.0406 (14)0.0529 (16)0.0035 (12)0.0364 (14)0.0016 (12)

Geometric parameters (Å, °)

O1—C111.438 (3)C8—H80.9300
O1—H1O0.87 (4)C9—C101.433 (3)
O2—C191.439 (3)C11—C121.544 (3)
O2—H2O0.94 (5)C11—H110.9800
C1—C21.361 (3)C12—C131.523 (3)
C1—C91.437 (3)C12—H12A0.9700
C1—C111.533 (3)C12—H12B0.9700
C2—C31.425 (4)C13—C141.395 (4)
C2—H20.9300C13—C181.408 (3)
C3—C41.356 (5)C14—C151.386 (4)
C3—H30.9300C14—H140.9300
C4—C101.404 (4)C15—C161.382 (4)
C4—H40.9300C15—H150.9300
C5—C61.353 (5)C16—C171.375 (5)
C5—C101.430 (4)C16—H160.9300
C5—H50.9300C17—C181.397 (3)
C6—C71.402 (5)C17—H170.9300
C6—H60.9300C18—C191.504 (4)
C7—C81.358 (4)C19—H19A0.9700
C7—H70.9300C19—H19B0.9700
C8—C91.422 (4)
C11—O1—H1O103 (3)C1—C11—C12111.80 (16)
C19—O2—H2O101 (3)O1—C11—H11108.8
C2—C1—C9119.7 (2)C1—C11—H11108.8
C2—C1—C11120.3 (2)C12—C11—H11108.8
C9—C1—C11120.0 (2)C13—C12—C11113.55 (17)
C1—C2—C3121.3 (3)C13—C12—H12A108.9
C1—C2—H2119.4C11—C12—H12A108.9
C3—C2—H2119.4C13—C12—H12B108.9
C4—C3—C2120.0 (3)C11—C12—H12B108.9
C4—C3—H3120.0H12A—C12—H12B107.7
C2—C3—H3120.0C14—C13—C18117.9 (2)
C3—C4—C10121.1 (2)C14—C13—C12118.1 (2)
C3—C4—H4119.4C18—C13—C12124.0 (2)
C10—C4—H4119.4C15—C14—C13122.1 (3)
C6—C5—C10121.8 (3)C15—C14—H14119.0
C6—C5—H5119.1C13—C14—H14119.0
C10—C5—H5119.1C16—C15—C14119.5 (3)
C5—C6—C7119.7 (3)C16—C15—H15120.2
C5—C6—H6120.2C14—C15—H15120.2
C7—C6—H6120.2C17—C16—C15119.5 (3)
C8—C7—C6120.9 (3)C17—C16—H16120.3
C8—C7—H7119.5C15—C16—H16120.3
C6—C7—H7119.5C16—C17—C18121.8 (2)
C7—C8—C9121.6 (2)C16—C17—H17119.1
C7—C8—H8119.2C18—C17—H17119.1
C9—C8—H8119.2C17—C18—C13119.2 (2)
C8—C9—C10117.6 (2)C17—C18—C19118.2 (2)
C8—C9—C1123.9 (2)C13—C18—C19122.6 (2)
C10—C9—C1118.5 (2)O2—C19—C18112.9 (2)
C4—C10—C5122.2 (2)O2—C19—H19A109.0
C4—C10—C9119.5 (2)C18—C19—H19A109.0
C5—C10—C9118.3 (3)O2—C19—H19B109.0
O1—C11—C1111.1 (2)C18—C19—H19B109.0
O1—C11—C12107.45 (19)H19A—C19—H19B107.8
C9—C1—C2—C30.5 (3)C2—C1—C11—O123.3 (3)
C11—C1—C2—C3178.2 (2)C9—C1—C11—O1−159.00 (19)
C1—C2—C3—C4−0.3 (4)C2—C1—C11—C12−96.7 (3)
C2—C3—C4—C100.0 (4)C9—C1—C11—C1281.0 (2)
C10—C5—C6—C71.4 (5)O1—C11—C12—C1378.1 (2)
C5—C6—C7—C8−1.0 (5)C1—C11—C12—C13−159.79 (19)
C6—C7—C8—C9−0.2 (4)C11—C12—C13—C1486.8 (3)
C7—C8—C9—C100.9 (3)C11—C12—C13—C18−91.5 (3)
C7—C8—C9—C1−179.2 (3)C18—C13—C14—C152.4 (3)
C2—C1—C9—C8179.7 (2)C12—C13—C14—C15−176.0 (2)
C11—C1—C9—C82.1 (3)C13—C14—C15—C16−0.9 (4)
C2—C1—C9—C10−0.4 (3)C14—C15—C16—C17−1.2 (4)
C11—C1—C9—C10−178.10 (18)C15—C16—C17—C181.9 (4)
C3—C4—C10—C5−179.4 (3)C16—C17—C18—C13−0.3 (3)
C3—C4—C10—C90.1 (4)C16—C17—C18—C19178.3 (2)
C6—C5—C10—C4178.8 (3)C14—C13—C18—C17−1.8 (3)
C6—C5—C10—C9−0.7 (4)C12—C13—C18—C17176.5 (2)
C8—C9—C10—C4180.0 (2)C14—C13—C18—C19179.7 (2)
C1—C9—C10—C40.2 (3)C12—C13—C18—C19−2.0 (3)
C8—C9—C10—C5−0.5 (3)C17—C18—C19—O2−90.6 (3)
C1—C9—C10—C5179.7 (2)C13—C18—C19—O288.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.87 (4)1.94 (4)2.721 (3)148 (4)
O2—H2O···O10.94 (5)1.79 (4)2.721 (3)169 (4)

Symmetry codes: (i) x, −y, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5147).

References

  • Bruker (2004). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Gałdecki, Z., Grochulski, P., Luciak, B., Wawrzak, Z. & Duax, W. L. (1984). Acta Cryst. C40, 1197–1198.
  • Hoyos-Guerrero, M. A., Martínez-Carrera, S. & García-Blanco, S. (1983). Acta Cryst. C39, 118–119.
  • Manivel, P., Hathwar, V. R., Mohanaroopan, S., Prabakaran, K. & Khan, F. N. (2009). Acta Cryst. E65, o406. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON Chemical Crystallography Laboratory, University of Oxford, England.

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