PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o6.
Published online 2007 December 6. doi:  10.1107/S1600536807061697
PMCID: PMC2914896

(E)-Methyl 3-{3-[(4-bromo­phen­oxy)­methyl]phen­yl}acrylate

Abstract

In the mol­ecule of the title compound, C17H15BrO3, the rings make a dihedral angle of 75.54 (17)°. In the crystal structure, inter­molecular C—H(...)O hydrogen bonds link the mol­ecules into centrosymmetric dimers, and the π-stacked dimers inter­act with neighbouring dimers via C—H(...)π stacking inter­actions.

Related literature

For general background, see: de Fraine et al. (1991 [triangle]); Zhang & Ji (1992 [triangle]); Janiak (2000 [triangle]). For related literature, see: Ren et al. (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-000o6-scheme1.jpg

Experimental

Crystal data

  • C17H15BrO3
  • M r = 347.20
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-000o6-efi1.jpg
  • a = 15.5226 (9) Å
  • b = 5.9390 (3) Å
  • c = 34.775 (2) Å
  • V = 3205.9 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.57 mm−1
  • T = 292 (2) K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001a [triangle]) T min = 0.627, T max = 0.783
  • 30716 measured reflections
  • 3147 independent reflections
  • 1604 reflections with I > 2σ(I)
  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.162
  • S = 1.02
  • 3147 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2001b [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061697/hk2392sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061697/hk2392Isup2.hkl

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

Acknowledgments

We gratefully acknowledge the financial support of this work by the National Basic Research Program of China (grant No. 2003CB114400) and the National Natural Science Foundation of China (grant No. 20372023).

supplementary crystallographic information

Comment

Phenyl acrylate and its derivatives are important compounds because of their agrochemical and medical applications (de Fraine et al., 1991; Zhang & Ji, 1992). We report herein the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (C1—C6) and B (C8—C13) are, of course, planar, and they are oriented at a dihedral angle of A/B = 75.54 (17)°.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2) and the π-stacked dimers interact with neighbouring dimers via C–H/π stacking interactions (Table 1) (Janiak, 2000), in which both of them seem to be effective in the stabilization of the structure.

Experimental

(E)-methyl 3-(3-(bromomethyl)phenyl)acrylate, (II), was firstly synthesized, (yield; 52.8%), according to a literature method (Ren et al., 2007). For the preparation of the title compound, (I), 4-bromophenol (2.0 mmol) and potassium carbonate (1.2 mmol) was added to a solution of compound (II) (2.0 mmol) in acetone (30 ml). The mixture was stirred at 329 K for 5 h, the solvent was removed under reduced pressure, and the residue was purified by chromatography (silica gel with 5% ethyl acetate in petroleum ether). Colorless crystals of (I) suitable for X-ray analysis were grown from methanol.

Refinement

H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
Fig. 3.
The formation of the title compound.

Crystal data

C17H15BrO3F000 = 1408
Mr = 347.20Dx = 1.439 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3230 reflections
a = 15.5226 (9) Åθ = 2.3–18.7º
b = 5.9390 (3) ŵ = 2.57 mm1
c = 34.775 (2) ÅT = 292 (2) K
V = 3205.9 (3) Å3Block, colorless
Z = 80.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer3147 independent reflections
Radiation source: fine-focus sealed tube1604 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.061
T = 292(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2001a)h = −19→19
Tmin = 0.627, Tmax = 0.783k = −7→7
30716 measured reflectionsl = −39→42

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.162  w = 1/[σ2(Fo2) + (0.0796P)2 + 0.4215P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3147 reflectionsΔρmax = 0.43 e Å3
191 parametersΔρmin = −0.36 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Br10.40930 (5)0.23555 (10)0.518514 (16)0.1544 (4)
O10.36979 (14)0.7793 (4)0.66326 (7)0.0701 (7)
O20.3798 (2)0.5459 (6)0.87722 (9)0.1199 (11)
O30.3379 (2)0.8260 (5)0.91548 (8)0.1118 (10)
C10.3993 (3)0.4150 (7)0.56360 (11)0.0898 (12)
C20.3295 (3)0.3823 (7)0.58702 (11)0.0857 (11)
H20.28760.27650.58070.103*
C30.3223 (2)0.5087 (6)0.62015 (10)0.0757 (10)
H30.27490.48820.63620.091*
C40.3841 (2)0.6647 (6)0.62979 (10)0.0619 (8)
C50.4538 (3)0.6952 (7)0.60590 (11)0.0824 (11)
H50.49590.80080.61200.099*
C60.4606 (3)0.5678 (8)0.57284 (12)0.1048 (14)
H60.50790.58720.55670.126*
C70.4336 (2)0.9377 (6)0.67551 (10)0.0679 (9)
H7A0.44061.05510.65640.082*
H7B0.48860.86290.67900.082*
C80.40363 (19)1.0367 (5)0.71267 (10)0.0596 (8)
C90.41060 (19)0.9171 (5)0.74654 (10)0.0588 (8)
H90.43670.77610.74620.071*
C100.37953 (19)1.0021 (5)0.78124 (10)0.0573 (8)
C110.3427 (2)1.2169 (5)0.78140 (11)0.0649 (9)
H110.32271.27870.80430.078*
C120.3361 (2)1.3359 (6)0.74792 (11)0.0711 (9)
H120.31101.47810.74810.085*
C130.3661 (2)1.2477 (6)0.71394 (12)0.0702 (9)
H130.36121.33130.69140.084*
C140.3823 (2)0.8606 (6)0.81570 (10)0.0678 (9)
H140.40470.71680.81220.081*
C150.3574 (2)0.9096 (6)0.85094 (10)0.0782 (10)
H150.33781.05390.85660.094*
C160.3602 (2)0.7391 (8)0.88138 (12)0.0839 (11)
C170.3380 (4)0.6729 (10)0.94758 (13)0.1363 (19)
H17A0.29470.55980.94370.204*
H17B0.32590.75450.97080.204*
H17C0.39350.60240.94960.204*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.2067 (8)0.1611 (7)0.0952 (5)−0.0426 (5)0.0403 (4)−0.0565 (4)
O10.0677 (14)0.0822 (16)0.0602 (14)−0.0103 (13)0.0043 (11)−0.0070 (12)
O20.153 (3)0.111 (2)0.095 (2)0.054 (2)0.0227 (19)0.028 (2)
O30.146 (3)0.125 (2)0.0641 (18)0.019 (2)0.0085 (17)0.0156 (17)
C10.122 (3)0.083 (3)0.065 (2)−0.012 (3)0.011 (2)−0.012 (2)
C20.101 (3)0.086 (3)0.070 (2)−0.020 (2)−0.002 (2)−0.003 (2)
C30.073 (2)0.093 (3)0.061 (2)−0.012 (2)0.0019 (17)−0.004 (2)
C40.068 (2)0.066 (2)0.051 (2)0.0013 (18)−0.0010 (16)0.0095 (17)
C50.089 (3)0.091 (3)0.067 (2)−0.016 (2)0.012 (2)−0.002 (2)
C60.120 (3)0.117 (4)0.077 (3)−0.024 (3)0.032 (2)−0.014 (3)
C70.068 (2)0.071 (2)0.065 (2)−0.0073 (18)0.0012 (16)0.0018 (18)
C80.0560 (19)0.058 (2)0.064 (2)−0.0026 (16)−0.0043 (15)−0.0005 (17)
C90.0608 (19)0.0459 (18)0.070 (2)0.0039 (15)−0.0045 (16)−0.0035 (17)
C100.0540 (18)0.054 (2)0.064 (2)0.0023 (15)−0.0053 (15)−0.0004 (17)
C110.064 (2)0.056 (2)0.074 (2)0.0021 (16)0.0009 (17)−0.0127 (18)
C120.075 (2)0.0505 (19)0.088 (3)0.0072 (17)−0.002 (2)0.007 (2)
C130.074 (2)0.062 (2)0.075 (3)−0.0012 (19)−0.0049 (19)0.0131 (19)
C140.070 (2)0.070 (2)0.064 (2)0.0064 (18)−0.0031 (17)−0.0047 (19)
C150.090 (3)0.076 (2)0.068 (2)0.017 (2)−0.001 (2)0.003 (2)
C160.080 (3)0.104 (3)0.067 (3)0.021 (2)0.003 (2)0.009 (2)
C170.165 (5)0.167 (5)0.077 (3)0.014 (4)0.009 (3)0.034 (3)

Geometric parameters (Å, °)

Br1—C11.902 (4)C9—H90.9300
C1—C61.355 (6)C10—C111.398 (4)
C1—C21.369 (5)C10—C141.464 (5)
C2—C31.380 (5)C11—C121.366 (5)
C2—H20.9300C11—H110.9300
C3—C41.375 (5)C12—C131.374 (5)
C3—H30.9300C12—H120.9300
C4—O11.367 (4)C13—H130.9300
C4—C51.376 (5)C14—C151.317 (4)
C5—C61.380 (5)C14—H140.9300
C5—H50.9300C15—C161.466 (5)
C6—H60.9300C15—H150.9300
C7—O11.431 (4)C16—O21.196 (4)
C7—C81.494 (5)C16—O31.339 (5)
C7—H7A0.9700C17—O31.440 (5)
C7—H7B0.9700C17—H17A0.9600
C8—C91.380 (5)C17—H17B0.9600
C8—C131.382 (4)C17—H17C0.9600
C9—C101.394 (4)
C6—C1—C2120.7 (4)C9—C10—C11118.4 (3)
C6—C1—Br1120.9 (3)C9—C10—C14119.3 (3)
C2—C1—Br1118.4 (3)C11—C10—C14122.2 (3)
C1—C2—C3118.9 (4)C12—C11—C10120.0 (3)
C1—C2—H2120.5C12—C11—H11120.0
C3—C2—H2120.5C10—C11—H11120.0
C4—C3—C2120.9 (3)C11—C12—C13120.7 (3)
C4—C3—H3119.6C11—C12—H12119.7
C2—C3—H3119.6C13—C12—H12119.7
O1—C4—C3115.5 (3)C12—C13—C8121.0 (3)
O1—C4—C5125.2 (3)C12—C13—H13119.5
C3—C4—C5119.4 (3)C8—C13—H13119.5
C4—C5—C6119.4 (4)C15—C14—C10128.7 (3)
C4—C5—H5120.3C15—C14—H14115.6
C6—C5—H5120.3C10—C14—H14115.6
C1—C6—C5120.7 (4)C14—C15—C16120.7 (4)
C1—C6—H6119.7C14—C15—H15119.6
C5—C6—H6119.7C16—C15—H15119.6
O1—C7—C8107.5 (3)O2—C16—O3122.9 (4)
O1—C7—H7A110.2O2—C16—C15125.7 (4)
C8—C7—H7A110.2O3—C16—C15111.4 (4)
O1—C7—H7B110.2O3—C17—H17A109.5
C8—C7—H7B110.2O3—C17—H17B109.5
H7A—C7—H7B108.5H17A—C17—H17B109.5
C9—C8—C13118.2 (3)O3—C17—H17C109.5
C9—C8—C7120.7 (3)H17A—C17—H17C109.5
C13—C8—C7121.0 (3)H17B—C17—H17C109.5
C8—C9—C10121.7 (3)C4—O1—C7117.9 (2)
C8—C9—H9119.2C16—O3—C17116.3 (4)
C10—C9—H9119.2
C6—C1—C2—C30.4 (6)C9—C10—C11—C121.4 (5)
Br1—C1—C2—C3178.9 (3)C14—C10—C11—C12−175.3 (3)
C1—C2—C3—C4−0.3 (6)C10—C11—C12—C13−0.6 (5)
C2—C3—C4—O1−180.0 (3)C11—C12—C13—C80.1 (5)
C2—C3—C4—C50.3 (5)C9—C8—C13—C12−0.4 (5)
O1—C4—C5—C6179.9 (3)C7—C8—C13—C12178.0 (3)
C3—C4—C5—C6−0.4 (6)C9—C10—C14—C15179.2 (3)
C2—C1—C6—C5−0.5 (7)C11—C10—C14—C15−4.1 (5)
Br1—C1—C6—C5−179.0 (3)C10—C14—C15—C16176.0 (3)
C4—C5—C6—C10.5 (6)C14—C15—C16—O2−4.0 (7)
O1—C7—C8—C977.1 (3)C14—C15—C16—O3175.8 (3)
O1—C7—C8—C13−101.2 (3)C3—C4—O1—C7177.7 (3)
C13—C8—C9—C101.2 (4)C5—C4—O1—C7−2.7 (5)
C7—C8—C9—C10−177.1 (3)C8—C7—O1—C4−179.2 (3)
C8—C9—C10—C11−1.8 (4)O2—C16—O3—C17−0.5 (6)
C8—C9—C10—C14175.1 (3)C15—C16—O3—C17179.7 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.932.453.370 (6)172
C12—H12···Cg2ii0.932.993.677 (3)132

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, −y−1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2392).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
  • Bruker (2001). SMART (Version 5.628) and SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fraine, P. J. de & Martin, A. (1991). US Patent 5 055 471.
  • Janiak, C. (2000). J. Chem. Soc. Dalton Trans pp. 3885–3896.
  • Ren, X.-L., Peng, H. & He, H.-W. (2007). Acta Cryst. E63, o2080–o2081.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Sheldrick, G. M. (2001a). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2001b). SHELXTL (Version 5.0). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Zhang, L. P. & Ji, Z. Z. (1992). Acta Pharm. Sinica, 27, 817–823. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography