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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1033.
Published online 2010 April 10. doi:  10.1107/S1600536810012018
PMCID: PMC2979021

3-(1-Hydr­oxy-2-phenyl­prop-2-en-1-yl)phenol

Abstract

Two independent pseudo-enanti­omeric mol­ecules comprise the asymmetric unit in the title compound, C15H14O2. While the central O—C—C—C residue approaches planarity [torsion angles = −15.8 (3) (mol­ecule a) and 15.4 (3)° (mol­ecule b)], the benzene rings are approximately orthogonal [the dihedral angles formed between the benzene rings are 62.89 (12) (mol­ecule a) and 80.15 (12)° (mol­ecule b)]. Two-dimensional arrays in the ab plane sustained by O—H(...)O hydrogen bonding are found in the crystal structure.

Related literature

For the synthesis of the title compound and the motivation for its study, see: Singh et al. (2010 [triangle]).

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Object name is e-66-o1033-scheme1.jpg

Experimental

Crystal data

  • C15H14O2
  • M r = 226.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1033-efi1.jpg
  • a = 9.1301 (2) Å
  • b = 10.2026 (2) Å
  • c = 24.8379 (6) Å
  • V = 2313.67 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.27 × 0.13 × 0.13 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.883, T max = 1
  • 31791 measured reflections
  • 2368 independent reflections
  • 2150 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.084
  • S = 1.15
  • 2368 reflections
  • 311 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]), DIAMOND (Brandenburg, 2006 [triangle]) and MarvinSketch (Chemaxon, 2009 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012018/hg2665sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012018/hg2665Isup2.hkl

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

Acknowledgments

We thank FAPESP (07/59404–2 to HAS), CNPq (472237/2008–0 to IC, 300613/2007 to HAS, and 306532/2009–3 to JZ-S) and CAPES (808/2009 to JZ-S and IC) for financial support.

supplementary crystallographic information

Comment

The title compound, (I), was prepared in connection with a study of the synthesis of α,β-epoxy ketones using a palladium-catalyzed epoxidation-oxidation sequence (Singh et al., 2010). Two independent molecules, molecule a (Fig. 1) and molecule b (Fig. 2), comprise the crystallographic asymmetric unit. Molecules a and b are related by a non-crystallographic centre of inversion. Close intramolecular O2···H9b and O4···H24b contacts which close S(6) motifs are noted, Table 1. These interactions are probably responsible for the near planarity of the O2–C7–C8–C9 and O4–C22–C23–C24 residues as seen in the respective torsion angles of -15.8 (3) and 15.4 (3)°. The benzene rings are approximately orthogonal [the dihedral angles formed between the benzene rings is 62.89 (12) ° (molecule a) and 80.15 (12) ° (molecule b)].

In the crystal packing, O–H···O interactions predominate, Table 1, and lead to the formation of two-dimensional arrays in the ab plane, Fig. 3, that stack along the c axis, Fig. 4.

Experimental

The synthesis was described in Singh et al. (2010) and crystals were grown by slow evaporation from a solution of 15% of acetyl acetate in hexane.

Refinement

The H atoms were geometrically placed (O–H = 0.84 Å and C–H = 0.95–1.00 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O). In the absence of significant anomalous scattering effects, 1752 Friedel pairs were averaged in the final refinement.

Figures

Fig. 1.
The molecular structure of the first independent molecule in (I) showing atom labelling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms).
Fig. 2.
The molecular structure of the second independent molecule in (I) showing atom labelling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms).
Fig. 3.
The supramolecular arrangement showing the formation of two-dimensional arrays in the ab plane.
Fig. 4.
The stacking of the two-dimensional arrays along the c axis.

Crystal data

C15H14O2F(000) = 960
Mr = 226.28Dx = 1.299 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9974 reflections
a = 9.1301 (2) Åθ = 2.5–25.0°
b = 10.2026 (2) ŵ = 0.09 mm1
c = 24.8379 (6) ÅT = 100 K
V = 2313.67 (9) Å3Block, colourless
Z = 80.27 × 0.13 × 0.13 mm

Data collection

Bruker SMART APEXII diffractometer2368 independent reflections
Radiation source: sealed tube2150 reflections with I > 2σ(I)
graphiteRint = 0.042
[var phi] and ω scansθmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.883, Tmax = 1k = −12→11
31791 measured reflectionsl = −29→29

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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.15w = 1/[σ2(Fo2) + (0.0381P)2 + 0.6989P] where P = (Fo2 + 2Fc2)/3
2368 reflections(Δ/σ)max < 0.001
311 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = −0.15 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 > 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)

xyzUiso*/Ueq
O11.06075 (18)0.29142 (16)0.21652 (7)0.0217 (4)
H1O0.97660.25810.21630.033*
O20.70773 (18)0.69539 (17)0.21929 (6)0.0203 (4)
H2O0.77190.71600.24200.031*
C11.0535 (3)0.4174 (2)0.19749 (8)0.0177 (5)
C20.9221 (3)0.4834 (3)0.19232 (9)0.0177 (5)
H20.83320.44180.20230.021*
C30.9201 (3)0.6112 (2)0.17244 (9)0.0169 (5)
C41.0502 (3)0.6719 (3)0.15824 (9)0.0189 (5)
H41.04920.75900.14470.023*
C51.1816 (3)0.6054 (2)0.16377 (9)0.0194 (5)
H51.27080.64740.15410.023*
C61.1841 (3)0.4781 (3)0.18328 (9)0.0194 (5)
H61.27440.43270.18690.023*
C70.7742 (2)0.6817 (2)0.16736 (9)0.0176 (5)
H70.79170.77100.15200.021*
C80.6701 (3)0.6085 (2)0.13080 (9)0.0177 (5)
C90.5564 (3)0.5408 (2)0.14915 (10)0.0204 (5)
H9A0.49290.49730.12470.025*
H9B0.53840.53590.18680.025*
C100.7000 (3)0.6172 (2)0.07155 (9)0.0182 (5)
C110.6005 (3)0.6817 (3)0.03877 (10)0.0260 (6)
H110.51630.72130.05430.031*
C120.6225 (3)0.6892 (3)−0.01631 (10)0.0288 (6)
H120.55400.7345−0.03830.035*
C130.7432 (3)0.6313 (3)−0.03926 (10)0.0270 (6)
H130.75820.6362−0.07710.032*
C140.8429 (3)0.5659 (3)−0.00699 (10)0.0286 (6)
H140.92570.5247−0.02280.034*
C150.8223 (3)0.5602 (3)0.04816 (10)0.0242 (6)
H150.89250.51710.07010.029*
O30.43410 (18)−0.19891 (17)0.22734 (7)0.0221 (4)
H3O0.5183−0.23210.22740.033*
O40.78763 (17)0.18479 (17)0.20933 (6)0.0200 (4)
H4O0.73100.20910.23410.030*
C160.4372 (3)−0.0816 (2)0.20043 (9)0.0171 (5)
C170.5664 (3)−0.0131 (2)0.19299 (9)0.0186 (5)
H170.6560−0.04810.20610.022*
C180.5656 (3)0.1067 (2)0.16646 (9)0.0168 (5)
C190.4346 (3)0.1569 (2)0.14687 (9)0.0205 (5)
H190.43350.23810.12820.025*
C200.3058 (3)0.0881 (2)0.15472 (9)0.0208 (5)
H200.21620.12280.14150.025*
C210.3063 (3)−0.0308 (3)0.18165 (9)0.0188 (5)
H210.2173−0.07720.18720.023*
C220.7091 (3)0.1805 (2)0.15946 (9)0.0180 (5)
H220.68730.27220.14760.022*
C230.8034 (3)0.1145 (2)0.11719 (9)0.0181 (5)
C240.9210 (3)0.0451 (3)0.13067 (10)0.0237 (6)
H24A0.97620.00150.10360.028*
H24B0.94990.03910.16730.028*
C250.7532 (3)0.1273 (2)0.06044 (9)0.0198 (5)
C260.6886 (3)0.2420 (3)0.04143 (10)0.0291 (6)
H260.67480.31360.06530.035*
C270.6439 (3)0.2536 (3)−0.01169 (11)0.0367 (7)
H270.59910.3323−0.02390.044*
C280.6648 (3)0.1505 (3)−0.04687 (11)0.0349 (7)
H280.63590.1585−0.08350.042*
C290.7273 (3)0.0368 (3)−0.02884 (10)0.0325 (7)
H290.7414−0.0342−0.05300.039*
C300.7702 (3)0.0245 (3)0.02443 (10)0.0258 (6)
H300.8119−0.05560.03650.031*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0130 (8)0.0196 (9)0.0326 (9)−0.0014 (8)−0.0031 (8)0.0047 (8)
O20.0157 (9)0.0261 (9)0.0192 (8)0.0022 (8)−0.0011 (7)−0.0020 (8)
C10.0173 (12)0.0196 (13)0.0163 (11)−0.0006 (11)−0.0021 (10)−0.0016 (10)
C20.0105 (11)0.0241 (14)0.0186 (11)−0.0027 (11)−0.0003 (9)−0.0010 (10)
C30.0148 (12)0.0191 (13)0.0167 (11)0.0003 (11)−0.0027 (9)−0.0034 (10)
C40.0194 (12)0.0205 (14)0.0169 (11)−0.0013 (11)−0.0009 (10)−0.0009 (10)
C50.0140 (12)0.0239 (14)0.0205 (11)−0.0079 (11)0.0009 (10)−0.0031 (11)
C60.0120 (12)0.0251 (14)0.0212 (11)0.0015 (11)−0.0011 (10)−0.0029 (10)
C70.0157 (12)0.0172 (12)0.0197 (11)−0.0014 (11)−0.0002 (9)0.0015 (10)
C80.0124 (12)0.0159 (13)0.0248 (12)0.0032 (11)−0.0013 (10)−0.0007 (10)
C90.0142 (12)0.0235 (14)0.0236 (12)−0.0002 (11)−0.0026 (10)−0.0011 (11)
C100.0151 (12)0.0131 (12)0.0263 (12)−0.0042 (11)−0.0008 (10)−0.0006 (10)
C110.0214 (14)0.0273 (14)0.0293 (13)0.0040 (12)−0.0024 (11)0.0007 (12)
C120.0275 (15)0.0305 (15)0.0283 (13)0.0014 (13)−0.0069 (12)0.0050 (12)
C130.0319 (15)0.0264 (14)0.0226 (12)−0.0094 (13)0.0003 (11)0.0001 (11)
C140.0243 (14)0.0334 (16)0.0282 (13)−0.0034 (13)0.0043 (11)−0.0058 (12)
C150.0186 (13)0.0274 (14)0.0266 (12)0.0011 (12)−0.0021 (11)−0.0010 (11)
O30.0142 (9)0.0208 (9)0.0313 (9)0.0014 (8)0.0024 (7)0.0046 (8)
O40.0149 (8)0.0252 (9)0.0198 (8)−0.0019 (8)0.0012 (7)−0.0015 (7)
C160.0157 (12)0.0163 (12)0.0194 (11)−0.0012 (11)0.0025 (10)−0.0034 (10)
C170.0137 (12)0.0216 (14)0.0204 (11)0.0005 (11)−0.0003 (10)−0.0025 (10)
C180.0143 (12)0.0183 (13)0.0178 (11)−0.0012 (11)−0.0001 (9)−0.0036 (10)
C190.0198 (13)0.0191 (14)0.0227 (12)0.0015 (11)0.0001 (10)−0.0006 (10)
C200.0123 (12)0.0244 (14)0.0255 (12)−0.0001 (11)−0.0031 (10)−0.0018 (11)
C210.0136 (12)0.0216 (13)0.0211 (11)−0.0045 (11)0.0017 (10)−0.0037 (10)
C220.0181 (12)0.0167 (12)0.0192 (11)−0.0018 (11)−0.0024 (10)0.0012 (10)
C230.0146 (12)0.0163 (12)0.0235 (11)−0.0056 (11)0.0025 (10)−0.0004 (10)
C240.0175 (13)0.0263 (14)0.0273 (13)−0.0031 (12)0.0021 (11)−0.0024 (11)
C250.0137 (12)0.0219 (13)0.0239 (12)−0.0058 (11)0.0033 (10)0.0012 (10)
C260.0357 (16)0.0253 (14)0.0262 (13)−0.0008 (13)0.0011 (12)−0.0013 (11)
C270.0452 (19)0.0330 (16)0.0318 (15)−0.0030 (14)−0.0044 (13)0.0088 (14)
C280.0398 (17)0.0419 (18)0.0229 (13)−0.0148 (15)−0.0025 (13)0.0022 (12)
C290.0343 (16)0.0360 (16)0.0272 (13)−0.0089 (14)0.0029 (12)−0.0085 (12)
C300.0230 (14)0.0271 (14)0.0273 (13)−0.0030 (12)0.0024 (11)−0.0026 (11)

Geometric parameters (Å, °)

O1—C11.371 (3)O3—C161.371 (3)
O1—H1O0.8400O3—H3O0.8400
O2—C71.432 (3)O4—C221.432 (3)
O2—H2O0.8400O4—H4O0.8400
C1—C21.382 (3)C16—C211.383 (3)
C1—C61.389 (4)C16—C171.384 (3)
C2—C31.394 (4)C17—C181.389 (3)
C2—H20.9500C17—H170.9500
C3—C41.385 (3)C18—C191.388 (3)
C3—C71.520 (3)C18—C221.521 (3)
C4—C51.386 (3)C19—C201.383 (3)
C4—H40.9500C19—H190.9500
C5—C61.387 (4)C20—C211.386 (4)
C5—H50.9500C20—H200.9500
C6—H60.9500C21—H210.9500
C7—C81.512 (3)C22—C231.516 (3)
C7—H71.0000C22—H221.0000
C8—C91.327 (3)C23—C241.329 (3)
C8—C101.499 (3)C23—C251.488 (3)
C9—H9A0.9500C24—H24A0.9500
C9—H9B0.9500C24—H24B0.9500
C10—C111.386 (3)C25—C301.388 (3)
C10—C151.387 (3)C25—C261.393 (4)
C11—C121.385 (4)C26—C271.386 (4)
C11—H110.9500C26—H260.9500
C12—C131.374 (4)C27—C281.381 (4)
C12—H120.9500C27—H270.9500
C13—C141.384 (4)C28—C291.368 (4)
C13—H130.9500C28—H280.9500
C14—C151.384 (3)C29—C301.385 (4)
C14—H140.9500C29—H290.9500
C15—H150.9500C30—H300.9500
C1—O1—H1O109.5C16—O3—H3O109.5
C7—O2—H2O109.5C22—O4—H4O109.5
O1—C1—C2122.1 (2)O3—C16—C21118.3 (2)
O1—C1—C6117.6 (2)O3—C16—C17121.6 (2)
C2—C1—C6120.3 (2)C21—C16—C17120.1 (2)
C1—C2—C3120.0 (2)C16—C17—C18120.2 (2)
C1—C2—H2120.0C16—C17—H17119.9
C3—C2—H2120.0C18—C17—H17119.9
C4—C3—C2119.8 (2)C19—C18—C17119.7 (2)
C4—C3—C7121.3 (2)C19—C18—C22121.3 (2)
C2—C3—C7118.9 (2)C17—C18—C22119.0 (2)
C3—C4—C5119.9 (2)C20—C19—C18119.7 (2)
C3—C4—H4120.0C20—C19—H19120.1
C5—C4—H4120.0C18—C19—H19120.1
C4—C5—C6120.5 (2)C19—C20—C21120.6 (2)
C4—C5—H5119.8C19—C20—H20119.7
C6—C5—H5119.8C21—C20—H20119.7
C5—C6—C1119.5 (2)C16—C21—C20119.6 (2)
C5—C6—H6120.3C16—C21—H21120.2
C1—C6—H6120.3C20—C21—H21120.2
O2—C7—C8108.83 (18)O4—C22—C23109.16 (19)
O2—C7—C3110.03 (18)O4—C22—C18110.34 (18)
C8—C7—C3111.52 (19)C23—C22—C18110.42 (19)
O2—C7—H7108.8O4—C22—H22109.0
C8—C7—H7108.8C23—C22—H22109.0
C3—C7—H7108.8C18—C22—H22109.0
C9—C8—C10120.7 (2)C24—C23—C25122.3 (2)
C9—C8—C7122.8 (2)C24—C23—C22121.4 (2)
C10—C8—C7116.5 (2)C25—C23—C22116.2 (2)
C8—C9—H9A120.0C23—C24—H24A120.0
C8—C9—H9B120.0C23—C24—H24B120.0
H9A—C9—H9B120.0H24A—C24—H24B120.0
C11—C10—C15118.7 (2)C30—C25—C26117.7 (2)
C11—C10—C8119.1 (2)C30—C25—C23120.6 (2)
C15—C10—C8122.2 (2)C26—C25—C23121.7 (2)
C12—C11—C10120.8 (2)C27—C26—C25121.3 (3)
C12—C11—H11119.6C27—C26—H26119.4
C10—C11—H11119.6C25—C26—H26119.4
C13—C12—C11120.1 (2)C28—C27—C26119.8 (3)
C13—C12—H12119.9C28—C27—H27120.1
C11—C12—H12119.9C26—C27—H27120.1
C12—C13—C14119.6 (2)C29—C28—C27119.8 (2)
C12—C13—H13120.2C29—C28—H28120.1
C14—C13—H13120.2C27—C28—H28120.1
C15—C14—C13120.3 (3)C28—C29—C30120.5 (3)
C15—C14—H14119.9C28—C29—H29119.7
C13—C14—H14119.9C30—C29—H29119.7
C14—C15—C10120.4 (2)C29—C30—C25121.0 (3)
C14—C15—H15119.8C29—C30—H30119.5
C10—C15—H15119.8C25—C30—H30119.5
O1—C1—C2—C3−179.59 (19)O3—C16—C17—C18−178.75 (19)
C6—C1—C2—C30.4 (3)C21—C16—C17—C18−0.2 (3)
C1—C2—C3—C4−0.4 (3)C16—C17—C18—C19−0.7 (3)
C1—C2—C3—C7−179.8 (2)C16—C17—C18—C22179.3 (2)
C2—C3—C4—C50.1 (3)C17—C18—C19—C201.1 (3)
C7—C3—C4—C5179.4 (2)C22—C18—C19—C20−179.0 (2)
C3—C4—C5—C60.3 (3)C18—C19—C20—C21−0.4 (4)
C4—C5—C6—C1−0.2 (3)O3—C16—C21—C20179.43 (19)
O1—C1—C6—C5179.91 (19)C17—C16—C21—C200.9 (3)
C2—C1—C6—C5−0.1 (3)C19—C20—C21—C16−0.5 (3)
C4—C3—C7—O2−117.5 (2)C19—C18—C22—O4132.6 (2)
C2—C3—C7—O261.8 (3)C17—C18—C22—O4−47.4 (3)
C4—C3—C7—C8121.6 (2)C19—C18—C22—C23−106.6 (2)
C2—C3—C7—C8−59.0 (3)C17—C18—C22—C2373.3 (3)
O2—C7—C8—C9−15.8 (3)O4—C22—C23—C2415.4 (3)
C3—C7—C8—C9105.8 (3)C18—C22—C23—C24−106.1 (3)
O2—C7—C8—C10163.3 (2)O4—C22—C23—C25−167.12 (19)
C3—C7—C8—C10−75.2 (3)C18—C22—C23—C2571.4 (3)
C9—C8—C10—C1165.5 (3)C24—C23—C25—C3033.9 (4)
C7—C8—C10—C11−113.6 (3)C22—C23—C25—C30−143.6 (2)
C9—C8—C10—C15−113.0 (3)C24—C23—C25—C26−145.8 (3)
C7—C8—C10—C1567.9 (3)C22—C23—C25—C2636.8 (3)
C15—C10—C11—C120.1 (4)C30—C25—C26—C27−0.6 (4)
C8—C10—C11—C12−178.5 (2)C23—C25—C26—C27179.1 (3)
C10—C11—C12—C130.6 (4)C25—C26—C27—C28−0.7 (4)
C11—C12—C13—C14−0.2 (4)C26—C27—C28—C291.1 (4)
C12—C13—C14—C15−0.9 (4)C27—C28—C29—C30−0.2 (4)
C13—C14—C15—C101.6 (4)C28—C29—C30—C25−1.1 (4)
C11—C10—C15—C14−1.2 (4)C26—C25—C30—C291.4 (4)
C8—C10—C15—C14177.3 (2)C23—C25—C30—C29−178.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9b···O20.952.392.726 (3)101
C24—H24b···O40.952.342.708 (3)102
O1—H1O···O40.841.892.727 (2)175
O2—H2O···O1i0.842.002.823 (2)168
O3—H3O···O2ii0.841.892.728 (2)174
O4—H4O···O3iii0.842.022.825 (2)161

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2665).

References

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