organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N-{2-[2-(2,6-Di­chloro-3,5-di­meth­oxy­phen­yl)ethen­yl]phen­yl}acetamide

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bFaculty of Pharmacy, Universiti Teknologi MARA, 40450 Shah Alam, Selangor Darul Ehsan, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 24 January 2009; accepted 26 January 2009; online 31 January 2009)

The C=C double bond in the title substituted stilbene, C18H17Cl2NO3, has a trans arrangement of the aryl substit­uents. The aromatic ring of the 2-acetyl­amino­phenyl substit­uent is twisted by 39.9 (3)° with respect to the central C—C=C—C unit and that of the 2,6-dichloro-3,5-dimethoxy­phenyl substitutent is twisted by 42.7 (3)°.

Related literature

The compound was synthesized by a ferric chloride-promoted highly atropodiastereoselective cascade reaction, a reaction that illustrates the utility of radical cations in indolostilbene synthesis; see: Ahmad et al. (2009[Ahmad, K., Thomas, N. F., Mukhtar, M. R., Noorbatcha, I., Weber, J.-F. F., Nafiah, M. A., Velu, S. S., Takeya, K., Morita, H., Lim, C.-G., Hadi, A. H. A. & Awang, K. (2009). Tetrahedron, 65, 1504-1516.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17Cl2NO3

  • Mr = 366.23

  • Triclinic, [P \overline 1]

  • a = 7.5646 (3) Å

  • b = 9.1485 (3) Å

  • c = 12.2969 (5) Å

  • α = 78.561 (2)°

  • β = 77.716 (2)°

  • γ = 85.969 (3)°

  • V = 814.65 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.42 mm−1

  • T = 100 (2) K

  • 0.30 × 0.03 × 0.03 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.886, Tmax = 0.988

  • 6677 measured reflections

  • 3657 independent reflections

  • 2490 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.117

  • S = 0.99

  • 3657 reflections

  • 220 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Comment top

The compound was synthesized by a ferric-chloride promoted, highly atropodiastereoselective cascade reaction, a reaction that illustrates the utility of radical cations in indolostilbene synthesis. The description of the synthesis is given in a recent study (Ahmad et al., 2009).

Related literature top

The compound was synthesized by a ferric chloride-promoted highly atropodiastereoselective cascade reaction, a reaction that illustrates the utility of radical cations in indolostilbene synthesis; see: Ahmad et al. (2009).

Experimental top

The synthesis is described in an earlier report (Ahmad et al., 2009).

Refinement top

Carbon-bound H atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The nitrogen-bound H-atom was similarly treated (N—H 0.88 Å, U(H) = 1.2U(N)).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 C18H17Cl2NO3 at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.
N-{2-[2-(2,6-Dichloro-3,5-dimethoxyphenyl)ethenyl]phenyl}acetamide top
Crystal data top
C18H17Cl2NO3Z = 2
Mr = 366.23F(000) = 380
Triclinic, P1Dx = 1.493 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5646 (3) ÅCell parameters from 1123 reflections
b = 9.1485 (3) Åθ = 2.6–26.5°
c = 12.2969 (5) ŵ = 0.42 mm1
α = 78.561 (2)°T = 100 K
β = 77.716 (2)°Prism, colourless
γ = 85.969 (3)°0.30 × 0.03 × 0.03 mm
V = 814.65 (5) Å3
Data collection top
Bruker SMART APEX
diffractometer
3657 independent reflections
Radiation source: fine-focus sealed tube2490 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.886, Tmax = 0.988k = 1111
6677 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.046P)2]
where P = (Fo2 + 2Fc2)/3
3657 reflections(Δ/σ)max = 0.001
220 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C18H17Cl2NO3γ = 85.969 (3)°
Mr = 366.23V = 814.65 (5) Å3
Triclinic, P1Z = 2
a = 7.5646 (3) ÅMo Kα radiation
b = 9.1485 (3) ŵ = 0.42 mm1
c = 12.2969 (5) ÅT = 100 K
α = 78.561 (2)°0.30 × 0.03 × 0.03 mm
β = 77.716 (2)°
Data collection top
Bruker SMART APEX
diffractometer
3657 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2490 reflections with I > 2σ(I)
Tmin = 0.886, Tmax = 0.988Rint = 0.048
6677 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 0.99Δρmax = 0.40 e Å3
3657 reflectionsΔρmin = 0.37 e Å3
220 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.21992 (9)0.40664 (7)0.21221 (5)0.02175 (18)
Cl20.28411 (9)0.66314 (7)0.56854 (5)0.01944 (18)
O10.3311 (3)0.68767 (19)0.08280 (14)0.0248 (5)
O20.4014 (2)0.90427 (18)0.39962 (15)0.0203 (4)
O30.1911 (3)0.2547 (2)0.96831 (17)0.0353 (5)
N10.1666 (3)0.3365 (2)0.78526 (18)0.0198 (5)
H10.17340.41730.73220.024*
C10.2581 (3)0.5380 (3)0.3861 (2)0.0141 (5)
C20.2725 (3)0.5540 (3)0.2691 (2)0.0162 (6)
C30.3281 (4)0.6856 (3)0.1940 (2)0.0171 (6)
C40.3763 (4)0.8042 (3)0.2354 (2)0.0183 (6)
H40.41900.89280.18450.022*
C50.3624 (3)0.7936 (3)0.3506 (2)0.0158 (6)
C60.3045 (3)0.6611 (3)0.4245 (2)0.0149 (5)
C70.3852 (4)0.8217 (3)0.0026 (2)0.0285 (7)
H7A0.37230.81020.07290.043*
H7B0.51190.84050.00090.043*
H7C0.30850.90600.02500.043*
C80.4638 (4)1.0415 (3)0.3273 (2)0.0232 (6)
H8A0.48521.11180.37350.035*
H8B0.37211.08430.28360.035*
H8C0.57681.02250.27530.035*
C90.1833 (3)0.4005 (3)0.4615 (2)0.0154 (6)
H90.08830.35590.44130.019*
C100.2381 (3)0.3337 (3)0.5558 (2)0.0144 (5)
H100.34010.37340.57230.017*
C110.1548 (3)0.2039 (3)0.6366 (2)0.0159 (6)
C120.1058 (4)0.0794 (3)0.6023 (2)0.0193 (6)
H120.12230.07780.52380.023*
C130.0330 (4)0.0426 (3)0.6812 (2)0.0207 (6)
H130.00160.12640.65650.025*
C140.0106 (4)0.0427 (3)0.7955 (2)0.0222 (6)
H140.03670.12750.84920.027*
C150.0568 (4)0.0805 (3)0.8323 (2)0.0203 (6)
H150.04040.08030.91110.024*
C160.1273 (4)0.2042 (3)0.7536 (2)0.0178 (6)
C170.1954 (4)0.3555 (3)0.8874 (2)0.0234 (6)
C180.2350 (4)0.5142 (3)0.8907 (2)0.0289 (7)
H18A0.29240.51470.95490.043*
H18B0.12160.57360.89930.043*
H18C0.31650.55720.82010.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0352 (4)0.0150 (3)0.0164 (3)0.0059 (3)0.0067 (3)0.0029 (3)
Cl20.0257 (4)0.0188 (3)0.0144 (3)0.0049 (3)0.0029 (3)0.0043 (3)
O10.0446 (13)0.0180 (10)0.0117 (9)0.0104 (9)0.0079 (9)0.0034 (8)
O20.0262 (11)0.0149 (9)0.0198 (10)0.0069 (8)0.0029 (8)0.0033 (8)
O30.0505 (14)0.0387 (12)0.0172 (11)0.0163 (11)0.0106 (10)0.0027 (10)
N10.0279 (13)0.0169 (11)0.0133 (11)0.0032 (10)0.0023 (10)0.0004 (9)
C10.0100 (12)0.0137 (12)0.0179 (13)0.0009 (9)0.0022 (10)0.0028 (10)
C20.0182 (14)0.0156 (12)0.0161 (13)0.0017 (10)0.0053 (11)0.0039 (11)
C30.0192 (14)0.0166 (13)0.0153 (13)0.0008 (11)0.0042 (11)0.0015 (11)
C40.0227 (15)0.0133 (12)0.0166 (14)0.0038 (11)0.0019 (11)0.0016 (11)
C50.0157 (13)0.0139 (12)0.0192 (14)0.0007 (10)0.0047 (11)0.0056 (11)
C60.0151 (13)0.0183 (13)0.0103 (12)0.0009 (10)0.0016 (10)0.0019 (10)
C70.0440 (19)0.0234 (15)0.0151 (14)0.0083 (14)0.0060 (13)0.0057 (12)
C80.0253 (16)0.0149 (13)0.0282 (16)0.0048 (11)0.0065 (13)0.0012 (12)
C90.0195 (14)0.0121 (12)0.0149 (13)0.0008 (10)0.0027 (11)0.0037 (10)
C100.0153 (13)0.0119 (12)0.0158 (13)0.0029 (10)0.0005 (11)0.0038 (10)
C110.0165 (14)0.0148 (13)0.0150 (13)0.0008 (10)0.0046 (11)0.0016 (11)
C120.0195 (14)0.0192 (13)0.0183 (14)0.0020 (11)0.0042 (11)0.0020 (11)
C130.0213 (15)0.0108 (12)0.0285 (16)0.0014 (11)0.0034 (12)0.0020 (11)
C140.0211 (15)0.0190 (14)0.0223 (15)0.0022 (11)0.0023 (12)0.0046 (12)
C150.0213 (15)0.0217 (14)0.0147 (13)0.0006 (11)0.0008 (11)0.0008 (11)
C160.0182 (14)0.0175 (13)0.0178 (14)0.0016 (11)0.0043 (11)0.0040 (11)
C170.0220 (15)0.0321 (16)0.0155 (14)0.0029 (13)0.0018 (12)0.0046 (13)
C180.0397 (19)0.0290 (16)0.0211 (15)0.0074 (14)0.0058 (14)0.0105 (13)
Geometric parameters (Å, º) top
Cl1—C21.742 (2)C8—H8A0.9800
Cl2—C61.748 (2)C8—H8B0.9800
O1—C31.359 (3)C8—H8C0.9800
O1—C71.437 (3)C9—C101.333 (4)
O2—C51.355 (3)C9—H90.9500
O2—C81.433 (3)C10—C111.471 (3)
O3—C171.211 (3)C10—H100.9500
N1—C171.365 (3)C11—C121.389 (3)
N1—C161.411 (3)C11—C161.410 (3)
N1—H10.8800C12—C131.386 (4)
C1—C61.397 (3)C12—H120.9500
C1—C21.399 (3)C13—C141.379 (4)
C1—C91.476 (3)C13—H130.9500
C2—C31.395 (3)C14—C151.386 (4)
C3—C41.387 (3)C14—H140.9500
C4—C51.382 (3)C15—C161.391 (4)
C4—H40.9500C15—H150.9500
C5—C61.398 (3)C17—C181.513 (4)
C7—H7A0.9800C18—H18A0.9800
C7—H7B0.9800C18—H18B0.9800
C7—H7C0.9800C18—H18C0.9800
C3—O1—C7118.2 (2)H8B—C8—H8C109.5
C5—O2—C8118.00 (19)C10—C9—C1125.3 (2)
C17—N1—C16128.5 (2)C10—C9—H9117.3
C17—N1—H1115.7C1—C9—H9117.3
C16—N1—H1115.7C9—C10—C11125.8 (2)
C6—C1—C2116.4 (2)C9—C10—H10117.1
C6—C1—C9124.0 (2)C11—C10—H10117.1
C2—C1—C9119.5 (2)C12—C11—C16118.6 (2)
C3—C2—C1122.4 (2)C12—C11—C10122.6 (2)
C3—C2—Cl1117.50 (19)C16—C11—C10118.8 (2)
C1—C2—Cl1120.11 (19)C13—C12—C11120.9 (2)
O1—C3—C4124.3 (2)C13—C12—H12119.6
O1—C3—C2116.4 (2)C11—C12—H12119.6
C4—C3—C2119.4 (2)C14—C13—C12120.1 (2)
C5—C4—C3120.1 (2)C14—C13—H13119.9
C5—C4—H4120.0C12—C13—H13119.9
C3—C4—H4120.0C13—C14—C15120.3 (2)
O2—C5—C4124.6 (2)C13—C14—H14119.8
O2—C5—C6115.8 (2)C15—C14—H14119.8
C4—C5—C6119.6 (2)C14—C15—C16119.8 (2)
C5—C6—C1122.2 (2)C14—C15—H15120.1
C5—C6—Cl2115.48 (18)C16—C15—H15120.1
C1—C6—Cl2122.29 (19)C15—C16—N1122.6 (2)
O1—C7—H7A109.5C15—C16—C11120.3 (2)
O1—C7—H7B109.5N1—C16—C11117.0 (2)
H7A—C7—H7B109.5O3—C17—N1123.4 (3)
O1—C7—H7C109.5O3—C17—C18122.7 (3)
H7A—C7—H7C109.5N1—C17—C18114.0 (2)
H7B—C7—H7C109.5C17—C18—H18A109.5
O2—C8—H8A109.5C17—C18—H18B109.5
O2—C8—H8B109.5H18A—C18—H18B109.5
H8A—C8—H8B109.5C17—C18—H18C109.5
O2—C8—H8C109.5H18A—C18—H18C109.5
H8A—C8—H8C109.5H18B—C18—H18C109.5
C6—C1—C2—C30.7 (4)C2—C1—C6—Cl2176.94 (19)
C9—C1—C2—C3174.7 (2)C9—C1—C6—Cl21.8 (4)
C6—C1—C2—Cl1179.43 (19)C6—C1—C9—C1040.8 (4)
C9—C1—C2—Cl15.2 (3)C2—C1—C9—C10144.2 (3)
C7—O1—C3—C40.9 (4)C1—C9—C10—C11174.6 (2)
C7—O1—C3—C2179.2 (2)C9—C10—C11—C1245.5 (4)
C1—C2—C3—O1178.1 (2)C9—C10—C11—C16136.0 (3)
Cl1—C2—C3—O11.8 (3)C16—C11—C12—C130.6 (4)
C1—C2—C3—C42.0 (4)C10—C11—C12—C13177.9 (2)
Cl1—C2—C3—C4178.1 (2)C11—C12—C13—C140.9 (4)
O1—C3—C4—C5177.6 (2)C12—C13—C14—C151.5 (4)
C2—C3—C4—C52.5 (4)C13—C14—C15—C160.5 (4)
C8—O2—C5—C40.8 (4)C14—C15—C16—N1176.0 (2)
C8—O2—C5—C6179.1 (2)C14—C15—C16—C111.1 (4)
C3—C4—C5—O2178.2 (2)C17—N1—C16—C1520.7 (4)
C3—C4—C5—C61.9 (4)C17—N1—C16—C11162.1 (3)
O2—C5—C6—C1179.5 (2)C12—C11—C16—C151.6 (4)
C4—C5—C6—C10.6 (4)C10—C11—C16—C15177.0 (2)
O2—C5—C6—Cl22.3 (3)C12—C11—C16—N1175.6 (2)
C4—C5—C6—Cl2177.7 (2)C10—C11—C16—N15.8 (4)
C2—C1—C6—C50.0 (4)C16—N1—C17—O30.3 (5)
C9—C1—C6—C5175.1 (2)C16—N1—C17—C18179.8 (2)

Experimental details

Crystal data
Chemical formulaC18H17Cl2NO3
Mr366.23
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.5646 (3), 9.1485 (3), 12.2969 (5)
α, β, γ (°)78.561 (2), 77.716 (2), 85.969 (3)
V3)814.65 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.30 × 0.03 × 0.03
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.886, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
6677, 3657, 2490
Rint0.048
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.117, 0.99
No. of reflections3657
No. of parameters220
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.37

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

The authors thank the University of Malaya for supporting this study (Science Fund grant No. 1402034013).

References

First citationAhmad, K., Thomas, N. F., Mukhtar, M. R., Noorbatcha, I., Weber, J.-F. F., Nafiah, M. A., Velu, S. S., Takeya, K., Morita, H., Lim, C.-G., Hadi, A. H. A. & Awang, K. (2009). Tetrahedron, 65, 1504–1516.  Web of Science CrossRef CAS Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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