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Acta Cryst. (2009). E65, o1289    [ doi:10.1107/S1600536809017395 ]

N'-{2-[2-(4-Methoxyphenyl)ethenyl]phenyl}acetamide

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

Abstract top

In the title compound, C17H17NO2, the phenylene rings are nearly coplanar [dihedral angle 7.3 (1)°]. The acetamido group is twisted out of the plane of the aromatic ring in order to form an N-H...O hydrogen bond to the acetamido group of an adjacent molecule, generating a helical chain running along the b 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 Ueq(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. Friedel pairs were merged.

Computing details top

Data collection: APEX2 (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-(4-Methoxyphenyl)ethenyl]phenyl}acetamide top
Crystal data top
C17H17NO2F000 = 284
Mr = 267.32Dx = 1.295 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3188 reflections
a = 5.4225 (1) Åθ = 2.6–28.3º
b = 9.4222 (2) ŵ = 0.09 mm−1
c = 13.5653 (3) ÅT = 100 K
β = 98.402 (1)ºBlock, colorless
V = 685.64 (2) Å30.25 × 0.20 × 0.20 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer		1605 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Monochromator: graphiteθmax = 27.5º
T = 100 Kθmin = 1.5º
ω scansh = −7→6
Absorption correction: Nonek = −11→12
4781 measured reflectionsl = −17→17
1654 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)] = 0.033H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.096  w = 1/[σ2(Fo2) + (0.0726P)2 + 0.080P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
1654 reflectionsΔρmax = 0.25 e Å−3
187 parametersΔρmin = −0.22 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C17H17NO2V = 685.64 (2) Å3
Mr = 267.32Z = 2
Monoclinic, P21Mo Kα
a = 5.4225 (1) ŵ = 0.09 mm−1
b = 9.4222 (2) ÅT = 100 K
c = 13.5653 (3) Å0.25 × 0.20 × 0.20 mm
β = 98.402 (1)º
Data collection top
Bruker SMART APEX
diffractometer		1654 independent reflections
Absorption correction: None1605 reflections with I > 2σ(I)
4781 measured reflectionsRint = 0.016
Refinement top
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.096Δρmax = 0.25 e Å−3
S = 1.05Δρmin = −0.22 e Å−3
1654 reflectionsAbsolute structure: ?
187 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5611 (2)−0.00004 (14)0.48762 (9)0.0210 (3)
O20.0298 (2)0.84291 (14)0.93515 (9)0.0198 (3)
N10.6516 (3)0.22034 (16)0.55197 (10)0.0142 (3)
H10.597 (4)0.3083 (13)0.5476 (17)0.021 (6)*
C10.8511 (3)0.18307 (17)0.62796 (11)0.0137 (3)
C21.0223 (3)0.07880 (19)0.60968 (12)0.0167 (3)
H20.99960.02940.54800.020*
C31.2247 (3)0.0471 (2)0.68092 (13)0.0178 (3)
H31.3400−0.02420.66830.021*
C41.2586 (3)0.12030 (19)0.77122 (13)0.0186 (4)
H41.39890.10010.81980.022*
C51.0881 (3)0.22226 (19)0.79020 (12)0.0163 (3)
H51.11300.27090.85220.020*
C60.8790 (3)0.25582 (17)0.72004 (12)0.0134 (3)
C70.5199 (3)0.12874 (19)0.48755 (12)0.0154 (3)
C80.3184 (3)0.1947 (2)0.41365 (12)0.0197 (4)
H8A0.19650.12190.38810.030*
H8B0.39250.23540.35830.030*
H8C0.23510.26970.44650.030*
C90.6925 (3)0.36010 (18)0.74194 (12)0.0138 (3)
H90.54920.37250.69340.017*
C100.7082 (3)0.43902 (18)0.82474 (12)0.0139 (3)
H100.85430.42810.87210.017*
C110.5219 (3)0.54060 (17)0.84945 (12)0.0133 (3)
C120.3218 (3)0.58920 (19)0.78032 (12)0.0167 (3)
H120.29930.55210.71450.020*
C130.1558 (3)0.6903 (2)0.80590 (12)0.0176 (4)
H130.02380.72300.75740.021*
C140.1830 (3)0.74359 (17)0.90263 (13)0.0159 (3)
C150.3793 (3)0.6960 (2)0.97288 (12)0.0174 (3)
H150.39880.73161.03910.021*
C160.5455 (3)0.59685 (19)0.94598 (12)0.0166 (3)
H160.67940.56610.99430.020*
C17−0.1752 (3)0.8937 (2)0.86533 (13)0.0195 (4)
H17A−0.27190.96220.89830.029*
H17B−0.28220.81380.84050.029*
H17C−0.11160.93990.80940.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0263 (7)0.0130 (6)0.0215 (6)0.0003 (5)−0.0038 (5)−0.0027 (5)
O20.0180 (6)0.0207 (7)0.0199 (6)0.0059 (5)0.0003 (4)−0.0056 (5)
N10.0181 (7)0.0110 (6)0.0128 (6)0.0011 (5)−0.0004 (5)−0.0001 (5)
C10.0146 (7)0.0124 (8)0.0138 (7)−0.0028 (6)0.0010 (6)0.0009 (6)
C20.0195 (8)0.0147 (8)0.0164 (7)−0.0003 (6)0.0038 (6)−0.0019 (6)
C30.0163 (7)0.0163 (8)0.0214 (8)0.0033 (7)0.0051 (6)0.0014 (7)
C40.0145 (7)0.0181 (8)0.0221 (8)0.0011 (7)−0.0005 (6)0.0026 (7)
C50.0171 (8)0.0165 (8)0.0146 (7)−0.0010 (7)−0.0002 (6)−0.0011 (6)
C60.0157 (8)0.0107 (7)0.0139 (7)−0.0019 (6)0.0019 (6)0.0002 (6)
C70.0191 (8)0.0149 (9)0.0122 (7)−0.0011 (6)0.0021 (6)−0.0003 (6)
C80.0239 (8)0.0181 (9)0.0151 (8)0.0006 (7)−0.0042 (6)0.0003 (6)
C90.0142 (7)0.0131 (7)0.0135 (7)0.0001 (6)−0.0003 (5)0.0003 (6)
C100.0160 (7)0.0115 (7)0.0139 (7)0.0002 (6)0.0014 (5)0.0020 (6)
C110.0153 (7)0.0108 (8)0.0140 (7)−0.0011 (6)0.0028 (6)0.0006 (6)
C120.0191 (8)0.0164 (8)0.0137 (7)−0.0003 (7)−0.0004 (6)−0.0031 (6)
C130.0155 (8)0.0186 (9)0.0173 (8)0.0007 (7)−0.0020 (6)−0.0021 (7)
C140.0151 (7)0.0126 (8)0.0203 (8)−0.0001 (6)0.0032 (6)−0.0010 (6)
C150.0225 (8)0.0174 (8)0.0121 (7)0.0011 (7)0.0022 (6)−0.0019 (6)
C160.0194 (8)0.0161 (8)0.0134 (7)0.0015 (7)−0.0008 (6)0.0008 (6)
C170.0165 (8)0.0179 (8)0.0236 (8)0.0030 (7)0.0012 (6)0.0005 (7)
Geometric parameters (Å, °) top
O1—C71.234 (2)C8—H8B0.9800
O2—C141.367 (2)C8—H8C0.9800
O2—C171.433 (2)C9—C101.339 (2)
N1—C71.355 (2)C9—H90.9500
N1—C11.425 (2)C10—C111.465 (2)
N1—H10.879 (10)C10—H100.9500
C1—C21.398 (2)C11—C161.401 (2)
C1—C61.413 (2)C11—C121.403 (2)
C2—C31.385 (2)C12—C131.389 (2)
C2—H20.9500C12—H120.9500
C3—C41.394 (3)C13—C141.393 (2)
C3—H30.9500C13—H130.9500
C4—C51.383 (2)C14—C151.395 (2)
C4—H40.9500C15—C161.384 (2)
C5—C61.406 (2)C15—H150.9500
C5—H50.9500C16—H160.9500
C6—C91.471 (2)C17—H17A0.9800
C7—C81.505 (2)C17—H17B0.9800
C8—H8A0.9800C17—H17C0.9800
C14—O2—C17117.70 (13)C10—C9—C6125.37 (14)
C7—N1—C1125.62 (15)C10—C9—H9117.3
C7—N1—H1114.7 (15)C6—C9—H9117.3
C1—N1—H1119.5 (15)C9—C10—C11126.38 (15)
C2—C1—C6120.61 (15)C9—C10—H10116.8
C2—C1—N1119.89 (14)C11—C10—H10116.8
C6—C1—N1119.45 (14)C16—C11—C12117.21 (15)
C3—C2—C1120.45 (15)C16—C11—C10119.28 (15)
C3—C2—H2119.8C12—C11—C10123.48 (14)
C1—C2—H2119.8C13—C12—C11121.52 (15)
C2—C3—C4119.71 (16)C13—C12—H12119.2
C2—C3—H3120.1C11—C12—H12119.2
C4—C3—H3120.1C12—C13—C14119.98 (15)
C5—C4—C3120.08 (16)C12—C13—H13120.0
C5—C4—H4120.0C14—C13—H13120.0
C3—C4—H4120.0O2—C14—C13124.45 (15)
C4—C5—C6121.68 (15)O2—C14—C15116.02 (14)
C4—C5—H5119.2C13—C14—C15119.53 (15)
C6—C5—H5119.2C16—C15—C14119.89 (15)
C5—C6—C1117.44 (15)C16—C15—H15120.1
C5—C6—C9121.59 (14)C14—C15—H15120.1
C1—C6—C9120.95 (14)C15—C16—C11121.86 (15)
O1—C7—N1123.22 (16)C15—C16—H16119.1
O1—C7—C8121.35 (16)C11—C16—H16119.1
N1—C7—C8115.43 (16)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—C238.5 (2)C1—C6—C9—C10−176.68 (16)
C7—N1—C1—C6−143.74 (16)C6—C9—C10—C11−178.20 (15)
C6—C1—C2—C3−1.2 (2)C9—C10—C11—C16169.14 (16)
N1—C1—C2—C3176.45 (14)C9—C10—C11—C12−12.9 (3)
C1—C2—C3—C4−0.4 (3)C16—C11—C12—C130.9 (2)
C2—C3—C4—C51.2 (3)C10—C11—C12—C13−177.13 (16)
C3—C4—C5—C6−0.4 (3)C11—C12—C13—C14−1.3 (3)
C4—C5—C6—C1−1.1 (2)C17—O2—C14—C131.1 (2)
C4—C5—C6—C9177.47 (16)C17—O2—C14—C15−179.56 (15)
C2—C1—C6—C52.0 (2)C12—C13—C14—O2−179.96 (16)
N1—C1—C6—C5−175.74 (15)C12—C13—C14—C150.8 (3)
C2—C1—C6—C9−176.66 (14)O2—C14—C15—C16−179.11 (15)
N1—C1—C6—C95.6 (2)C13—C14—C15—C160.2 (3)
C1—N1—C7—O1−0.4 (3)C14—C15—C16—C11−0.7 (3)
C1—N1—C7—C8−179.72 (14)C12—C11—C16—C150.1 (2)
C5—C6—C9—C104.8 (3)C10—C11—C16—C15178.23 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (1)2.03 (1)2.895 (2)169 (2)
Symmetry codes: (i) −x+1, y+1/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (1)2.03 (1)2.895 (2)169 (2)
Symmetry codes: (i) −x+1, y+1/2, −z+1.
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.