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Acta Cryst. (2009). E65, o1290    [ doi:10.1107/S1600536809017401 ]

N'-{2-[2-(3-Methoxyphenyl)ethenyl]phenyl}acetamide

K. Ahmad, N. F. Thomas, M. A. Nafiah, K. Awang and S. W. Ng

Abstract top

In the title compound, C17H17NO2, the phenylene rings are bent with respect to the carbon-carbon double bond [dihedral angle between rings = 39.6 (1)°]. The acetamido group is twisted out of the plane of the aromatic ring [dihedral angle = 44.2 (1)°] in order to form an N-H...O hydrogen bond to the acetamido group of an adjacent molecule, generating a zigzag chain running along the c axis.

Comment top

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Related literature top

The compound was synthesized in a study on indolostilbenes; see: Ahmad et al. (2009).

Experimental top

The compound was synthesized in a study on indolostilbenes (Ahmad et al., 2009). Crystals were grown from its solution in ethyl acetate.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times U~eq~(C). The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.88±0.01 Å; its temperature factor was refined.

Computing details top

Data collection: APEX2 software (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C17H17NO2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
N'-{2-[2-(3-Methoxyphenyl)ethenyl]phenyl}acetamide top
Crystal data top
C17H17NO2F000 = 568
Mr = 267.32Dx = 1.256 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1682 reflections
a = 14.5588 (5) Åθ = 2.4–27.7º
b = 10.3633 (4) ŵ = 0.08 mm−1
c = 9.3667 (3) ÅT = 100 K
β = 90.118 (1)ºPlate, colorless
V = 1413.22 (9) Å30.21 × 0.07 × 0.02 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		2036 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
Monochromator: graphiteθmax = 27.5º
T = 100 Kθmin = 1.4º
ω scansh = −18→18
Absorption correction: Nonek = −13→13
12919 measured reflectionsl = −12→12
3236 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.140  w = 1/[σ2(Fo2) + (0.0657P)2 + 0.3754P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3236 reflectionsΔρmax = 0.38 e Å−3
187 parametersΔρmin = −0.25 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C17H17NO2V = 1413.22 (9) Å3
Mr = 267.32Z = 4
Monoclinic, P21/cMo Kα
a = 14.5588 (5) ŵ = 0.08 mm−1
b = 10.3633 (4) ÅT = 100 K
c = 9.3667 (3) Å0.21 × 0.07 × 0.02 mm
β = 90.118 (1)º
Data collection top
Bruker SMART APEX
diffractometer		3236 independent reflections
Absorption correction: None2036 reflections with I > 2σ(I)
12919 measured reflectionsRint = 0.069
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.140H atoms treated by a mixture of
independent and constrained refinement
S = 1.01Δρmax = 0.38 e Å−3
3236 reflectionsΔρmin = −0.25 e Å−3
187 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.11400 (10)0.71029 (14)0.73510 (14)0.0246 (4)
O20.65965 (10)0.58338 (15)0.10659 (16)0.0273 (4)
N10.12402 (11)0.66372 (17)0.49961 (17)0.0177 (4)
H10.1185 (16)0.699 (2)0.4151 (15)0.032 (7)*
C10.14037 (13)0.5285 (2)0.5123 (2)0.0172 (4)
C20.08867 (14)0.4550 (2)0.6068 (2)0.0204 (5)
H20.04320.49550.66390.024*
C30.10283 (14)0.3241 (2)0.6183 (2)0.0243 (5)
H30.06860.27490.68530.029*
C40.16751 (15)0.2639 (2)0.5315 (2)0.0269 (5)
H40.17710.17340.53820.032*
C50.21760 (14)0.3364 (2)0.4357 (2)0.0236 (5)
H50.26010.29410.37460.028*
C60.20754 (13)0.4707 (2)0.4259 (2)0.0185 (4)
C70.10934 (13)0.7448 (2)0.6095 (2)0.0187 (4)
C80.08548 (16)0.8812 (2)0.5694 (2)0.0257 (5)
H8A0.12550.94100.62160.038*
H8B0.02130.89850.59410.038*
H8C0.09410.89310.46650.038*
C90.26855 (14)0.5474 (2)0.3343 (2)0.0208 (5)
H90.25070.63380.31450.025*
C100.34701 (14)0.5057 (2)0.2767 (2)0.0222 (5)
H100.36230.41770.29190.027*
C110.41182 (14)0.5822 (2)0.1925 (2)0.0206 (5)
C120.38525 (15)0.6915 (2)0.1148 (2)0.0242 (5)
H120.32300.71910.11560.029*
C130.45036 (16)0.7595 (2)0.0361 (2)0.0261 (5)
H130.43220.8334−0.01680.031*
C140.54070 (15)0.7208 (2)0.0343 (2)0.0223 (5)
H140.58440.7671−0.02080.027*
C150.56799 (14)0.6138 (2)0.1129 (2)0.0218 (5)
C160.50366 (14)0.5444 (2)0.1902 (2)0.0212 (5)
H160.52240.47010.24210.025*
C170.69172 (16)0.4821 (2)0.1966 (2)0.0302 (5)
H17A0.75860.47490.18820.045*
H17B0.66310.40050.16770.045*
H17C0.67550.50120.29590.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0362 (9)0.0232 (8)0.0144 (7)0.0009 (7)0.0007 (6)−0.0012 (6)
O20.0182 (8)0.0272 (9)0.0366 (9)−0.0019 (6)0.0023 (6)0.0044 (7)
N10.0207 (9)0.0181 (9)0.0144 (8)0.0017 (7)0.0011 (7)0.0019 (7)
C10.0157 (10)0.0204 (11)0.0156 (9)0.0000 (8)−0.0024 (8)−0.0020 (8)
C20.0162 (10)0.0245 (11)0.0203 (10)0.0016 (9)0.0011 (8)0.0000 (9)
C30.0232 (12)0.0231 (12)0.0266 (11)−0.0028 (9)0.0005 (9)0.0043 (9)
C40.0252 (12)0.0170 (11)0.0387 (13)−0.0006 (9)−0.0006 (10)−0.0002 (10)
C50.0186 (11)0.0227 (12)0.0296 (11)0.0013 (9)0.0017 (9)−0.0028 (10)
C60.0150 (10)0.0210 (11)0.0195 (10)−0.0009 (8)−0.0022 (8)−0.0026 (9)
C70.0150 (10)0.0214 (11)0.0196 (10)−0.0007 (8)0.0010 (8)−0.0007 (8)
C80.0349 (13)0.0208 (12)0.0213 (10)0.0048 (9)0.0023 (9)−0.0014 (9)
C90.0212 (11)0.0190 (11)0.0220 (10)0.0008 (9)−0.0011 (8)−0.0008 (9)
C100.0247 (12)0.0197 (11)0.0222 (10)0.0001 (9)0.0010 (9)−0.0009 (9)
C110.0225 (11)0.0233 (11)0.0160 (9)−0.0030 (9)0.0018 (8)−0.0051 (9)
C120.0220 (11)0.0268 (12)0.0238 (11)0.0020 (9)−0.0007 (9)−0.0017 (10)
C130.0313 (13)0.0237 (12)0.0234 (11)−0.0005 (10)−0.0024 (9)0.0028 (9)
C140.0241 (12)0.0215 (11)0.0213 (10)−0.0055 (9)0.0013 (8)0.0016 (9)
C150.0182 (11)0.0254 (12)0.0218 (10)−0.0016 (9)−0.0005 (8)−0.0055 (9)
C160.0238 (11)0.0194 (11)0.0203 (10)0.0004 (9)−0.0001 (8)−0.0007 (9)
C170.0205 (12)0.0338 (14)0.0361 (13)−0.0009 (10)−0.0031 (10)0.0052 (11)
Geometric parameters (Å, °) top
O1—C71.231 (2)C8—H8B0.9800
O2—C151.373 (2)C8—H8C0.9800
O2—C171.424 (3)C9—C101.336 (3)
N1—C71.346 (3)C9—H90.9500
N1—C11.426 (3)C10—C111.464 (3)
N1—H10.877 (10)C10—H100.9500
C1—C21.391 (3)C11—C161.394 (3)
C1—C61.405 (3)C11—C121.400 (3)
C2—C31.376 (3)C12—C131.393 (3)
C2—H20.9500C12—H120.9500
C3—C41.393 (3)C13—C141.375 (3)
C3—H30.9500C13—H130.9500
C4—C51.380 (3)C14—C151.388 (3)
C4—H40.9500C14—H140.9500
C5—C61.402 (3)C15—C161.386 (3)
C5—H50.9500C16—H160.9500
C6—C91.470 (3)C17—H17A0.9800
C7—C81.504 (3)C17—H17B0.9800
C8—H8A0.9800C17—H17C0.9800
C15—O2—C17117.48 (17)C10—C9—C6125.4 (2)
C7—N1—C1125.17 (17)C10—C9—H9117.3
C7—N1—H1114.4 (16)C6—C9—H9117.3
C1—N1—H1120.2 (16)C9—C10—C11126.5 (2)
C2—C1—C6120.73 (19)C9—C10—H10116.7
C2—C1—N1120.06 (18)C11—C10—H10116.7
C6—C1—N1119.19 (18)C16—C11—C12118.93 (19)
C3—C2—C1120.6 (2)C16—C11—C10118.36 (19)
C3—C2—H2119.7C12—C11—C10122.71 (19)
C1—C2—H2119.7C13—C12—C11119.8 (2)
C2—C3—C4119.8 (2)C13—C12—H12120.1
C2—C3—H3120.1C11—C12—H12120.1
C4—C3—H3120.1C14—C13—C12120.7 (2)
C5—C4—C3119.6 (2)C14—C13—H13119.6
C5—C4—H4120.2C12—C13—H13119.6
C3—C4—H4120.2C13—C14—C15119.9 (2)
C4—C5—C6121.8 (2)C13—C14—H14120.0
C4—C5—H5119.1C15—C14—H14120.0
C6—C5—H5119.1O2—C15—C16124.12 (19)
C5—C6—C1117.31 (19)O2—C15—C14115.96 (18)
C5—C6—C9120.78 (19)C16—C15—C14119.9 (2)
C1—C6—C9121.83 (19)C15—C16—C11120.7 (2)
O1—C7—N1122.77 (19)C15—C16—H16119.6
O1—C7—C8121.59 (18)C11—C16—H16119.6
N1—C7—C8115.64 (17)O2—C17—H17A109.5
C7—C8—H8A109.5O2—C17—H17B109.5
C7—C8—H8B109.5H17A—C17—H17B109.5
H8A—C8—H8B109.5O2—C17—H17C109.5
C7—C8—H8C109.5H17A—C17—H17C109.5
H8A—C8—H8C109.5H17B—C17—H17C109.5
H8B—C8—H8C109.5
C7—N1—C1—C242.6 (3)C1—C6—C9—C10162.9 (2)
C7—N1—C1—C6−138.9 (2)C6—C9—C10—C11−175.99 (18)
C6—C1—C2—C30.5 (3)C9—C10—C11—C16154.0 (2)
N1—C1—C2—C3178.97 (18)C9—C10—C11—C12−25.9 (3)
C1—C2—C3—C4−2.0 (3)C16—C11—C12—C130.5 (3)
C2—C3—C4—C50.7 (3)C10—C11—C12—C13−179.63 (19)
C3—C4—C5—C62.1 (3)C11—C12—C13—C14−0.2 (3)
C4—C5—C6—C1−3.5 (3)C12—C13—C14—C15−0.9 (3)
C4—C5—C6—C9173.33 (19)C17—O2—C15—C16−6.6 (3)
C2—C1—C6—C52.2 (3)C17—O2—C15—C14174.07 (18)
N1—C1—C6—C5−176.28 (18)C13—C14—C15—O2−179.00 (19)
C2—C1—C6—C9−174.62 (18)C13—C14—C15—C161.7 (3)
N1—C1—C6—C96.9 (3)O2—C15—C16—C11179.34 (19)
C1—N1—C7—O14.4 (3)C14—C15—C16—C11−1.4 (3)
C1—N1—C7—C8−174.86 (18)C12—C11—C16—C150.3 (3)
C5—C6—C9—C10−13.8 (3)C10—C11—C16—C15−179.58 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (1)1.93 (1)2.804 (2)175 (2)
Symmetry codes: (i) x, −y+3/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (1)1.93 (1)2.804 (2)175 (2)
Symmetry codes: (i) x, −y+3/2, z−1/2.
Acknowledgements top

We thank the University of Malaya for supporting this study.

references
References top

Ahmad, K., Thomas, N. F., Mukhtar, M. R., Noorbatcha, I., Faizal, W., Nafiah, J.-F., Azlan, M., Velu, S. S., Takeya, K., Morita, H., Lim, C.-G., Hadi, A. H. A. & Awang, K. (2009). Tetrahedron, 65, 1504–1516.

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.