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 June 1; 64(Pt 6): o1123.
Published online 2008 May 21. doi:  10.1107/S1600536808014700
PMCID: PMC2961564

3-[4-(Dimethyl­amino)phen­yl]-1-(2-pyrrol­yl)prop-2-en-1-one

Abstract

The molecule of the title compound, C15H16N2O, is non-planar with a dihedral angle of 16.0 (1)° between the pyrrole and benzene rings. The ketone double-bond displays an s–cis conformation with an O=C—C=C torsion angle of 7.9 (3) and an intramolecular C—H(...)O hydrogen bond. In the crystal structure, adjacent mol­ecules are paired through N—H(...)O hydrogen bonds into centrosymmetric dimers.

Related literature

For the pharmaceutical and biological activities of chalcones, see: Lin et al. (2002 [triangle]); Lunardi et al. (2003 [triangle]); Modzelewska et al. (2006 [triangle]); Opletalova (2000 [triangle]); Opletalova & Sedivy (1999 [triangle]); Sogawa et al. (1994 [triangle]). For the use of chalcones as photonic materials, see: Balaji et al. (2003 [triangle]); Indira et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1123-scheme1.jpg

Experimental

Crystal data

  • C15H16N2O
  • M r = 240.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1123-efi1.jpg
  • a = 11.0864 (16) Å
  • b = 12.0412 (17) Å
  • c = 10.6169 (16) Å
  • β = 112.294 (2)°
  • V = 1311.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.20 × 0.18 × 0.17 mm

Data collection

  • Bruker APEX area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.985, T max = 0.991
  • 6889 measured reflections
  • 2568 independent reflections
  • 1654 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.159
  • S = 1.09
  • 2568 reflections
  • 165 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014700/ez2122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014700/ez2122Isup2.hkl

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

Acknowledgments

The authors thank Hengyang Normal University for supporting this study.

supplementary crystallographic information

Comment

Chalcones and their analogues are of considerable interest because they possess broad pharmaceutical (Sogawa et al., 1994) and biological activities (Opletalova & Sedivy, 1999), such as anticancer (Modzelewska et al., 2006), antitubercular (Lin et al., 2002), trypanocidal (Lunardi et al., 2003), antifungal and antibacterial properties (Opletalova, 2000). Moreover, some substituted chalcones have also been studied as negative photoresist materials (Balaji et al., 2003) and non-linear optical materials (Indira et al., 2002). We report here a new chalcone compound, (I), Fig. 1.

The title compound reveals an s-cis conformation for the O1–C5–C6–C7 [torsion angle 7.9 (3)°] ketone motif. Differently to most substituted chalcones, compound (I) is nonplanar with a dihedral angle between the pyrrole ring and benzene ring of 16.0 (1)°. In the crystal packing, the –NH groups are involved as donors to form centrosymmetric dimers through N—H···O hydrogen bonding interactions as shown in Fig. 2.

Experimental

To a solution of 2-acetylpyrrole (1.09 g, 10.0 mmol) and 4-dimethylaminobenzaldehyde (1.49 g, 10.0 mmol) in 15 ml e thanol was added a solution of sodium hydroxide (0.40 g, 10.0 mmol) in 5 ml water at room temperature. After stirring 10 h, the solution was filtered. The resulting orange precipitate was washed with water and iced ethanol, and further recrystallized from acetone to afford orange block crystals of the title compound. Yield: 0.92 g (38.3%).

Refinement

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic and ethylene; 0.96 Å, Uiso= 1.2Ueq (C) for CH3 atoms, and d(N—H) = 0.86 Å, Uiso=1.2Ueq (N) for pyrrole nitrogen atom.

Figures

Fig. 1.
The molecular structure of (I) showing the atom numbering scheme, with displacement ellipsoids drawn at the 30% probability level, and H atoms as spheres of arbitrary radius.
Fig. 2.
Partial packing diagram of the title structure showing the N—H···O hydrogen bonding interactions as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C15H16N2OF000 = 512
Mr = 240.30Dx = 1.217 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1115 reflections
a = 11.0864 (16) Åθ = 2.6–23.4º
b = 12.0412 (17) ŵ = 0.08 mm1
c = 10.6169 (16) ÅT = 293 (2) K
β = 112.294 (2)ºBlock, orange
V = 1311.3 (3) Å30.20 × 0.18 × 0.17 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer2568 independent reflections
Radiation source: fine-focus sealed tube1654 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
T = 293(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 2.6º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.985, Tmax = 0.991k = −14→9
6889 measured reflectionsl = −10→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.159  w = 1/[σ2(Fo2) + (0.0637P)2 + 0.0839P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2568 reflectionsΔρmax = 0.13 e Å3
165 parametersΔρmin = −0.15 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
O10.39484 (17)0.01511 (13)0.82369 (16)0.0848 (6)
N10.53628 (17)0.17431 (15)1.00559 (18)0.0683 (6)
H1A0.54180.11001.04270.082*
N2−0.1228 (2)0.10473 (18)0.0104 (2)0.0821 (6)
C10.4663 (2)0.19776 (18)0.8722 (2)0.0583 (6)
C20.4841 (2)0.30924 (19)0.8553 (3)0.0726 (7)
H20.44800.34880.77440.087*
C30.5650 (2)0.3521 (2)0.9796 (3)0.0831 (8)
H30.59330.42520.99770.100*
C40.5953 (3)0.2667 (2)1.0701 (3)0.0823 (8)
H40.64830.27161.16190.099*
C50.3924 (2)0.11169 (19)0.7811 (2)0.0621 (6)
C60.3125 (2)0.14088 (19)0.6406 (2)0.0628 (6)
H60.32050.21110.60820.075*
C70.2285 (2)0.06891 (18)0.5581 (2)0.0642 (6)
H70.22570.00000.59650.077*
C80.1409 (2)0.08166 (17)0.4178 (2)0.0581 (6)
C90.0498 (3)−0.00039 (19)0.3551 (3)0.0776 (7)
H90.0479−0.06320.40520.093*
C10−0.0371 (2)0.0067 (2)0.2234 (2)0.0768 (7)
H10−0.0960−0.05090.18680.092*
C11−0.0389 (2)0.09835 (19)0.1430 (2)0.0623 (6)
C120.0526 (2)0.18180 (18)0.2049 (2)0.0666 (6)
H120.05470.24480.15500.080*
C130.1389 (2)0.17297 (17)0.3365 (2)0.0635 (6)
H130.19840.23000.37330.076*
C14−0.2165 (3)0.0175 (2)−0.0521 (3)0.0945 (9)
H14A−0.1716−0.0517−0.04540.142*
H14B−0.26420.0350−0.14620.142*
H14C−0.27590.0115−0.00610.142*
C15−0.1296 (3)0.2014 (3)−0.0725 (3)0.1092 (10)
H15A−0.18630.2556−0.05750.164*
H15B−0.16300.1804−0.16670.164*
H15C−0.04400.2325−0.04820.164*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.1096 (14)0.0608 (11)0.0631 (11)−0.0019 (9)0.0093 (9)0.0103 (8)
N10.0763 (13)0.0619 (12)0.0593 (12)−0.0020 (10)0.0172 (10)0.0020 (9)
N20.0801 (14)0.0857 (15)0.0640 (14)0.0035 (11)0.0088 (11)0.0010 (11)
C10.0588 (12)0.0576 (14)0.0562 (13)0.0046 (10)0.0192 (11)0.0052 (11)
C20.0758 (15)0.0639 (16)0.0775 (18)0.0004 (12)0.0285 (14)0.0081 (12)
C30.0896 (18)0.0669 (16)0.093 (2)−0.0156 (14)0.0349 (16)−0.0078 (16)
C40.0858 (18)0.0832 (19)0.0690 (17)−0.0157 (15)0.0194 (14)−0.0152 (15)
C50.0649 (14)0.0598 (14)0.0585 (14)0.0063 (11)0.0199 (11)0.0057 (11)
C60.0656 (13)0.0544 (13)0.0620 (14)0.0034 (11)0.0170 (12)0.0068 (11)
C70.0714 (14)0.0535 (13)0.0654 (15)0.0062 (11)0.0233 (13)0.0068 (11)
C80.0620 (13)0.0502 (13)0.0600 (14)0.0041 (10)0.0207 (11)0.0024 (10)
C90.0934 (18)0.0617 (15)0.0680 (17)−0.0140 (13)0.0195 (14)0.0066 (12)
C100.0816 (17)0.0723 (17)0.0676 (17)−0.0216 (13)0.0182 (14)−0.0045 (13)
C110.0607 (13)0.0655 (15)0.0574 (14)0.0096 (11)0.0188 (11)−0.0016 (11)
C120.0732 (15)0.0580 (14)0.0633 (15)0.0044 (12)0.0199 (13)0.0104 (11)
C130.0623 (13)0.0550 (14)0.0662 (15)−0.0023 (10)0.0164 (12)0.0014 (11)
C140.0762 (17)0.115 (2)0.0791 (19)−0.0055 (16)0.0143 (15)−0.0205 (16)
C150.116 (2)0.114 (2)0.0713 (19)0.0082 (19)0.0052 (17)0.0173 (17)

Geometric parameters (Å, °)

O1—C51.244 (2)C7—H70.9300
N1—C41.339 (3)C8—C91.388 (3)
N1—C11.361 (3)C8—C131.392 (3)
N1—H1A0.8600C9—C101.367 (3)
N2—C111.364 (3)C9—H90.9300
N2—C151.443 (3)C10—C111.391 (3)
N2—C141.449 (3)C10—H100.9300
C1—C21.379 (3)C11—C121.402 (3)
C1—C51.442 (3)C12—C131.366 (3)
C2—C31.383 (3)C12—H120.9300
C2—H20.9300C13—H130.9300
C3—C41.360 (3)C14—H14A0.9600
C3—H30.9300C14—H14B0.9600
C4—H40.9300C14—H14C0.9600
C5—C61.460 (3)C15—H15A0.9600
C6—C71.329 (3)C15—H15B0.9600
C6—H60.9300C15—H15C0.9600
C7—C81.446 (3)
C4—N1—C1109.6 (2)C13—C8—C7124.7 (2)
C4—N1—H1A125.2C10—C9—C8123.2 (2)
C1—N1—H1A125.2C10—C9—H9118.4
C11—N2—C15122.1 (2)C8—C9—H9118.4
C11—N2—C14121.4 (2)C9—C10—C11121.1 (2)
C15—N2—C14116.3 (2)C9—C10—H10119.4
N1—C1—C2106.5 (2)C11—C10—H10119.4
N1—C1—C5120.2 (2)N2—C11—C10121.6 (2)
C2—C1—C5133.3 (2)N2—C11—C12122.2 (2)
C1—C2—C3108.2 (2)C10—C11—C12116.3 (2)
C1—C2—H2125.9C13—C12—C11121.7 (2)
C3—C2—H2125.9C13—C12—H12119.2
C4—C3—C2106.8 (2)C11—C12—H12119.2
C4—C3—H3126.6C12—C13—C8122.4 (2)
C2—C3—H3126.6C12—C13—H13118.8
N1—C4—C3109.0 (2)C8—C13—H13118.8
N1—C4—H4125.5N2—C14—H14A109.5
C3—C4—H4125.5N2—C14—H14B109.5
O1—C5—C1119.9 (2)H14A—C14—H14B109.5
O1—C5—C6121.2 (2)N2—C14—H14C109.5
C1—C5—C6118.9 (2)H14A—C14—H14C109.5
C7—C6—C5121.2 (2)H14B—C14—H14C109.5
C7—C6—H6119.4N2—C15—H15A109.5
C5—C6—H6119.4N2—C15—H15B109.5
C6—C7—C8129.7 (2)H15A—C15—H15B109.5
C6—C7—H7115.2N2—C15—H15C109.5
C8—C7—H7115.2H15A—C15—H15C109.5
C9—C8—C13115.3 (2)H15B—C15—H15C109.5
C9—C8—C7120.0 (2)
C4—N1—C1—C20.2 (3)C6—C7—C8—C137.1 (4)
C4—N1—C1—C5−179.3 (2)C13—C8—C9—C10−0.4 (4)
N1—C1—C2—C3−0.1 (3)C7—C8—C9—C10179.2 (2)
C5—C1—C2—C3179.4 (2)C8—C9—C10—C110.1 (4)
C1—C2—C3—C40.0 (3)C15—N2—C11—C10177.3 (3)
C1—N1—C4—C3−0.2 (3)C14—N2—C11—C101.7 (3)
C2—C3—C4—N10.1 (3)C15—N2—C11—C12−4.6 (4)
N1—C1—C5—O1−1.6 (3)C14—N2—C11—C12179.8 (2)
C2—C1—C5—O1179.0 (2)C9—C10—C11—N2178.2 (2)
N1—C1—C5—C6176.55 (19)C9—C10—C11—C120.0 (4)
C2—C1—C5—C6−2.9 (4)N2—C11—C12—C13−178.0 (2)
O1—C5—C6—C77.9 (3)C10—C11—C12—C130.2 (3)
C1—C5—C6—C7−170.3 (2)C11—C12—C13—C8−0.5 (4)
C5—C6—C7—C8179.5 (2)C9—C8—C13—C120.6 (3)
C6—C7—C8—C9−172.4 (2)C7—C8—C13—C12−179.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.012.832 (2)161
C7—H7···O10.932.442.797 (3)103

Symmetry codes: (i) −x+1, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2122).

References

  • Balaji, R., Grande, D. & Nanjundan, S. (2003). React. Funct. Polym.56, 45–57.
  • Bruker (2002). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Indira, J., Prakash Karat, P. & Sarojini, B. K. (2002). J. Cryst. Growth, 242, 209–214.
  • Lin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem.10, 2795–2802. [PubMed]
  • Lunardi, F., Guzela, M., Rodrigues, A. T., Corrêa, R., Eger-Mangrich, I., Steindel, M., Grisard, E. C., Assreuy, J., Calixto, J. B. & Santos, A. R. S. (2003). Antimicrob. Agents Chemother.47, 1449–1451. [PMC free article] [PubMed]
  • Modzelewska, A., Pettit, C., Achanta, G., Davidson, N. E., Huang, P. & Khan, S. R. (2006). Bioorg. Med. Chem.14, 3491–3495. [PubMed]
  • Opletalova, V. (2000). Ceska Slov. Farm.49, 278–284. [PubMed]
  • Opletalova, V. & Sedivy, D. (1999). Ceska Slov. Farm.48, 252–255. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sogawa, S., Nihro, Y., Ueda, H., Miki, T., Matsumoto, H. & Satoh, T. (1994). Biol. Pharm. Bull.17, 251–256. [PubMed]

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