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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1289.
Published online 2009 May 14. doi:  10.1107/S1600536809017395
PMCID: PMC2969691

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

Abstract

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.

Related literature

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

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Object name is e-65-o1289-scheme1.jpg

Experimental

Crystal data

  • C17H17NO2
  • M r = 267.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1289-efi1.jpg
  • a = 5.4225 (1) Å
  • b = 9.4222 (2) Å
  • c = 13.5653 (3) Å
  • β = 98.402 (1)°
  • V = 685.64 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.25 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 4781 measured reflections
  • 1654 independent reflections
  • 1605 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.096
  • S = 1.05
  • 1654 reflections
  • 187 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017395/hg2513sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017395/hg2513Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

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

Refinement

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.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C17H17NO2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C17H17NO2F(000) = 284
Mr = 267.32Dx = 1.295 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3188 reflections
a = 5.4225 (1) Åθ = 2.6–28.3°
b = 9.4222 (2) ŵ = 0.09 mm1
c = 13.5653 (3) ÅT = 100 K
β = 98.402 (1)°Block, colorless
V = 685.64 (2) Å30.25 × 0.20 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer1605 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
graphiteθmax = 27.5°, θmin = 1.5°
ω scansh = −7→6
4781 measured reflectionsk = −11→12
1654 independent reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0726P)2 + 0.080P] where P = (Fo2 + 2Fc2)/3
1654 reflections(Δ/σ)max = 0.001
187 parametersΔρmax = 0.25 e Å3
2 restraintsΔρmin = −0.22 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2513).

References

  • 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. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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