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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1434–o1435.
Published online 2008 July 9. doi:  10.1107/S1600536808020539
PMCID: PMC2962066

(E)-3-(3,4-Dimethoxy­phen­yl)-1-(2-fur­yl)prop-2-en-1-one

Abstract

In the title mol­ecule, C15H14O4, the benzene and furyl rings are inclined to each other with a dihedral angle of 41.5 (1)°. An intra­molecular C—H(...)O hydrogen-bond inter­action generates an S(5) ring motif. In the crystal structure, mol­ecules are stacked along the b axis and the crystal packing is stabilized by inter­molecular C—H(...)O and C—H(...)π inter­actions. In addition, π–π stacking inter­actions with a centroid-to-centroid distance of 3.5855 (11) Å are observed.

Related literature

For related literature on the non-linear optical properties of chromophore derivatives, see: Agrinskaya et al. (1999 [triangle]). For other related literature, see: Chantrapromma et al. (2005 [triangle], 2006 [triangle]); Fun et al. (2006 [triangle]); Patil, Fun et al. (2007 [triangle]); Patil, Dharmaprakash et al. (2007 [triangle]); Patil et al. (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1434-scheme1.jpg

Experimental

Crystal data

  • C15H14O4
  • M r = 258.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1434-efi1.jpg
  • a = 21.5582 (5) Å
  • b = 5.6105 (1) Å
  • c = 10.4622 (3) Å
  • β = 101.510 (2)°
  • V = 1239.98 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100.0 (1) K
  • 0.42 × 0.05 × 0.04 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.947, T max = 0.996
  • 7017 measured reflections
  • 1997 independent reflections
  • 1707 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.104
  • S = 1.10
  • 1997 reflections
  • 174 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020539/lh2655sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020539/lh2655Isup2.hkl

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

Acknowledgments

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. This work was supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).

supplementary crystallographic information

Comment

Among the many types of NLO chromophores developed so far, the dipolar push–pull molecules consisting of electron donor and acceptor groups inter-bridged by a π-segment have received the predominant attention (Agrinskaya et al., 1999). As a part of the investigation of nonlinear compounds (Chantrapromma et al., 2005, 2006; Fun et al., 2006; Patil, Fun et al., 2007; Patil, Dharmaprakash et al., 2007; Patil et al., 2006), the title compound (I) has recently been prepared in our laboratory and its crystal structure is presented here. The non-centrosymmetric crystal of the title compound should exhibit second-order NLO properties.

The bond lengths and bond angles in (I) have normal values (Allen et al., 1987). The benzene and furyl rings in the molecule are essentially planar with the maximum deviation from planarity being 0.016 (2) Å for atom C10 and 0.003 (2) Å for atom C4 respectively. The dihedral angle between the phenyl and the furyl rings is 41.5 (1)°, indicating that they are twisted from each other.

An intramolecular C—H···O hydrogen bond generates a S(5) ring motif (Bernstein et al., 1995). In the crystal structure, the molecules are stacked along the b axis. The crystal packing is consolidated by C—H···O and C—H···π interactions. π–π interactions with the centroid···centroid(1 -x, y,3 - z) distance of 3.5855 (11) Å is observed.

Experimental

3,4-dimethoxybenzaldehyde (0.01 mol, 1.66 g m) in ethanol (20 ml) was mixed with 2-acetyl furan (0.01 mol, 1.01 ml) in 20 ml ethanol and the mixture was treated with 5 ml of 10% sodium hydroxide solution and stirred at room temperature for 6 h. The precipitate obtained was poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered, dried and recrystallized from N,N-dimethylformamide (DMF) by slow evaporation.

Refinement

H atoms were positioned geometrically [C—H = 0.93Å and 0.96 Å for methyl H atoms] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Uequ(C) methyl. The rotating group model was used for the methyl group hydrogen atoms. In the absence of significant anomalous dispersion effects 1283 Friedel pairs were merged.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. The dashed line indicates a hydrogen bond.
Fig. 2.
The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C15H14O4F000 = 544
Mr = 258.26Dx = 1.383 Mg m3
Monoclinic, C2Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 1982 reflections
a = 21.5582 (5) Åθ = 3.0–30.0º
b = 5.6105 (1) ŵ = 0.10 mm1
c = 10.4622 (3) ÅT = 100.0 (1) K
β = 101.510 (2)ºNeedle, colourless
V = 1239.98 (5) Å30.42 × 0.05 × 0.04 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer1997 independent reflections
Radiation source: fine-focus sealed tube1707 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 100.0(1) Kθmax = 30.2º
[var phi] and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −30→30
Tmin = 0.947, Tmax = 0.996k = −7→7
7017 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.104  w = 1/[σ2(Fo2) + (0.059P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
1997 reflectionsΔρmax = 0.29 e Å3
174 parametersΔρmin = −0.20 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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
O10.57239 (6)0.0466 (3)1.44832 (13)0.0232 (4)
O20.48812 (8)−0.1128 (3)1.23361 (16)0.0332 (4)
O30.20877 (6)0.3835 (3)0.77192 (13)0.0207 (3)
O40.25511 (6)0.7519 (3)0.67784 (12)0.0205 (3)
C10.55488 (9)0.4315 (4)1.39689 (18)0.0214 (5)
H1A0.53880.57031.35400.026*
C20.60096 (9)0.4149 (5)1.51546 (19)0.0243 (5)
H2A0.62110.54081.56480.029*
C30.60942 (8)0.1816 (5)1.54141 (19)0.0235 (5)
H3A0.63700.12011.61370.028*
C40.53928 (8)0.2049 (4)1.35948 (17)0.0186 (4)
C50.49518 (9)0.1039 (4)1.2480 (2)0.0208 (4)
C60.46005 (8)0.2776 (4)1.15509 (17)0.0195 (4)
H6A0.47110.43801.16140.023*
C70.41218 (8)0.2036 (4)1.06159 (18)0.0197 (4)
H7A0.40250.04201.06010.024*
C80.37371 (8)0.3532 (4)0.96152 (17)0.0177 (4)
C90.31001 (8)0.2882 (4)0.91378 (17)0.0178 (4)
H9A0.29390.15040.94430.021*
C100.27144 (8)0.4282 (4)0.82177 (17)0.0178 (4)
C110.29632 (8)0.6304 (4)0.77127 (17)0.0164 (4)
C120.35917 (8)0.6949 (4)0.81736 (18)0.0189 (4)
H12A0.37580.82940.78440.023*
C130.39718 (8)0.5570 (4)0.91321 (18)0.0189 (4)
H13A0.43890.60260.94510.023*
C140.18004 (8)0.1967 (4)0.83195 (19)0.0209 (4)
H14A0.13530.19600.79800.031*
H14B0.18780.22190.92450.031*
H14C0.19770.04650.81380.031*
C150.28193 (10)0.9223 (5)0.60272 (19)0.0232 (4)
H15A0.24970.97910.53240.035*
H15B0.31520.84840.56790.035*
H15C0.29891.05370.65740.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0204 (6)0.0220 (9)0.0236 (7)0.0022 (6)−0.0043 (5)0.0049 (7)
O20.0346 (8)0.0191 (9)0.0376 (9)0.0034 (7)−0.0128 (7)0.0013 (9)
O30.0168 (5)0.0235 (9)0.0198 (6)−0.0018 (6)−0.0014 (5)0.0065 (7)
O40.0204 (6)0.0228 (9)0.0175 (6)0.0022 (6)0.0015 (5)0.0081 (7)
C10.0210 (8)0.0222 (13)0.0196 (8)0.0002 (8)0.0003 (7)0.0021 (9)
C20.0227 (8)0.0295 (14)0.0187 (8)−0.0004 (9)−0.0009 (7)−0.0014 (10)
C30.0172 (8)0.0337 (15)0.0174 (8)0.0027 (9)−0.0021 (6)0.0028 (10)
C40.0158 (7)0.0211 (11)0.0173 (8)0.0028 (8)−0.0005 (6)0.0039 (9)
C50.0190 (8)0.0190 (12)0.0224 (9)0.0030 (8)−0.0005 (7)0.0003 (9)
C60.0187 (8)0.0201 (11)0.0176 (8)0.0029 (8)−0.0012 (6)0.0009 (9)
C70.0193 (8)0.0173 (11)0.0205 (9)0.0012 (8)−0.0008 (7)0.0006 (9)
C80.0176 (7)0.0179 (11)0.0161 (8)0.0043 (8)−0.0002 (6)−0.0015 (9)
C90.0197 (8)0.0159 (11)0.0168 (8)0.0014 (7)0.0015 (6)−0.0006 (8)
C100.0165 (7)0.0197 (11)0.0158 (8)0.0008 (7)−0.0001 (6)−0.0015 (9)
C110.0182 (8)0.0169 (11)0.0133 (8)0.0021 (7)0.0015 (6)−0.0010 (8)
C120.0197 (8)0.0204 (12)0.0167 (8)−0.0008 (8)0.0033 (6)0.0007 (9)
C130.0158 (7)0.0224 (12)0.0178 (8)0.0012 (8)0.0016 (6)−0.0026 (9)
C140.0189 (8)0.0234 (12)0.0194 (8)−0.0022 (8)0.0016 (6)0.0026 (9)
C150.0305 (9)0.0196 (12)0.0189 (8)0.0003 (9)0.0033 (7)0.0063 (9)

Geometric parameters (Å, °)

O1—C31.360 (3)C7—C81.464 (3)
O1—C41.377 (2)C7—H7A0.9300
O2—C51.231 (3)C8—C131.386 (3)
O3—C101.371 (2)C8—C91.412 (2)
O3—C141.425 (3)C9—C101.384 (3)
O4—C111.365 (2)C9—H9A0.9300
O4—C151.431 (3)C10—C111.402 (3)
C1—C41.353 (3)C11—C121.392 (2)
C1—C21.429 (2)C12—C131.396 (3)
C1—H1A0.9300C12—H12A0.9300
C2—C31.342 (4)C13—H13A0.9300
C2—H2A0.9300C14—H14A0.9600
C3—H3A0.9300C14—H14B0.9600
C4—C51.464 (3)C14—H14C0.9600
C5—C61.475 (3)C15—H15A0.9600
C6—C71.339 (2)C15—H15B0.9600
C6—H6A0.9300C15—H15C0.9600
C3—O1—C4105.99 (18)C10—C9—C8120.4 (2)
C10—O3—C14116.67 (15)C10—C9—H9A119.8
C11—O4—C15116.78 (14)C8—C9—H9A119.8
C4—C1—C2106.2 (2)O3—C10—C9124.77 (19)
C4—C1—H1A126.9O3—C10—C11115.27 (16)
C2—C1—H1A126.9C9—C10—C11119.95 (16)
C3—C2—C1106.4 (2)O4—C11—C12124.57 (19)
C3—C2—H2A126.8O4—C11—C10115.50 (15)
C1—C2—H2A126.8C12—C11—C10119.92 (17)
C2—C3—O1111.20 (17)C11—C12—C13119.73 (19)
C2—C3—H3A124.4C11—C12—H12A120.1
O1—C3—H3A124.4C13—C12—H12A120.1
C1—C4—O1110.20 (16)C8—C13—C12120.98 (16)
C1—C4—C5132.75 (19)C8—C13—H13A119.5
O1—C4—C5117.05 (19)C12—C13—H13A119.5
O2—C5—C4121.66 (19)O3—C14—H14A109.5
O2—C5—C6122.51 (18)O3—C14—H14B109.5
C4—C5—C6115.8 (2)H14A—C14—H14B109.5
C7—C6—C5119.7 (2)O3—C14—H14C109.5
C7—C6—H6A120.1H14A—C14—H14C109.5
C5—C6—H6A120.1H14B—C14—H14C109.5
C6—C7—C8126.1 (2)O4—C15—H15A109.5
C6—C7—H7A117.0O4—C15—H15B109.5
C8—C7—H7A117.0H15A—C15—H15B109.5
C13—C8—C9118.95 (17)O4—C15—H15C109.5
C13—C8—C7122.56 (16)H15A—C15—H15C109.5
C9—C8—C7118.5 (2)H15B—C15—H15C109.5
C4—C1—C2—C3−0.5 (3)C7—C8—C9—C10178.20 (18)
C1—C2—C3—O10.2 (3)C14—O3—C10—C98.3 (3)
C4—O1—C3—C20.2 (2)C14—O3—C10—C11−172.75 (17)
C2—C1—C4—O10.6 (2)C8—C9—C10—O3−178.34 (19)
C2—C1—C4—C5179.8 (2)C8—C9—C10—C112.8 (3)
C3—O1—C4—C1−0.5 (2)C15—O4—C11—C1214.7 (3)
C3—O1—C4—C5−179.81 (17)C15—O4—C11—C10−165.54 (18)
C1—C4—C5—O2−179.5 (2)O3—C10—C11—O4−1.2 (2)
O1—C4—C5—O2−0.4 (3)C9—C10—C11—O4177.80 (18)
C1—C4—C5—C60.5 (3)O3—C10—C11—C12178.59 (18)
O1—C4—C5—C6179.55 (16)C9—C10—C11—C12−2.4 (3)
O2—C5—C6—C79.9 (3)O4—C11—C12—C13−179.89 (18)
C4—C5—C6—C7−170.05 (18)C10—C11—C12—C130.3 (3)
C5—C6—C7—C8−178.99 (19)C9—C8—C13—C12−1.0 (3)
C6—C7—C8—C1329.9 (3)C7—C8—C13—C12179.74 (19)
C6—C7—C8—C9−149.4 (2)C11—C12—C13—C81.4 (3)
C13—C8—C9—C10−1.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1A···O2i0.932.323.247 (3)173
C3—H3A···O3ii0.932.423.338 (3)167
C7—H7A···O20.932.472.810 (3)101
C14—H14B···Cg1iii0.962.663.431 (2)137

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2655).

References

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  • Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H.-K., Sai Santosh Kumar, R. & Rao, D. N. (2007). J. Cryst. Growth, 303, 520–524.
  • Patil, P. S., Fun, H.-K., Chantrapromma, S. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2497–o2498.
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