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

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

doi:10.1107/S1600536809017401

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1290

doi:10.1107/S1600536809017401

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

Kartini Ahmad,^a Noel F. Thomas,^a Mohd Azlan Nafiah,^a Khalijah Awang ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 5 May 2009; accepted 8 May 2009; online 14 May 2009)

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.

Related literature

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

Experimental

Crystal data

C₁₇H₁₇NO₂
M_r = 267.32
Monoclinic, P 2₁ /c
a = 14.5588 (5) Å
b = 10.3633 (4) Å
c = 9.3667 (3) Å
β = 90.118 (1)°
V = 1413.22 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.21 × 0.07 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
12919 measured reflections
3236 independent reflections
2036 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.140
S = 1.01
3236 reflections
187 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88 (1)	1.93 (1)	2.804 (2)	175 (2)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 software (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017401/hg2514sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017401/hg2514Isup2.hkl

checkCIF report

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.

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

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

C₁₇H₁₇NO₂	F(000) = 568
M_r = 267.32	D_x = 1.256 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1682 reflections
a = 14.5588 (5) Å	θ = 2.4–27.7°
b = 10.3633 (4) Å	µ = 0.08 mm⁻¹
c = 9.3667 (3) Å	T = 100 K
β = 90.118 (1)°	Plate, colorless
V = 1413.22 (9) Å³	0.21 × 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 tube	R_int = 0.069
Graphite monochromator	θ_max = 27.5°, θ_min = 1.4°
ω scans	h = −18→18
12919 measured reflections	k = −13→13
3236 independent reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0657P)² + 0.3754P] where P = (F_o² + 2F_c²)/3
3236 reflections	(Δ/σ)_max = 0.001
187 parameters	Δρ_max = 0.38 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₁₇NO₂	V = 1413.22 (9) Å³
M_r = 267.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.5588 (5) Å	µ = 0.08 mm⁻¹
b = 10.3633 (4) Å	T = 100 K
c = 9.3667 (3) Å	0.21 × 0.07 × 0.02 mm
β = 90.118 (1)°

Data collection top

Bruker SMART APEX diffractometer	2036 reflections with I > 2σ(I)
12919 measured reflections	R_int = 0.069
3236 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.38 e Å⁻³
3236 reflections	Δρ_min = −0.25 e Å⁻³
187 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.11400 (10)	0.71029 (14)	0.73510 (14)	0.0246 (4)
O2	0.65965 (10)	0.58338 (15)	0.10659 (16)	0.0273 (4)
N1	0.12402 (11)	0.66372 (17)	0.49961 (17)	0.0177 (4)
H1	0.1185 (16)	0.699 (2)	0.4151 (15)	0.032 (7)*
C1	0.14037 (13)	0.5285 (2)	0.5123 (2)	0.0172 (4)
C2	0.08867 (14)	0.4550 (2)	0.6068 (2)	0.0204 (5)
H2	0.0432	0.4955	0.6639	0.024*
C3	0.10283 (14)	0.3241 (2)	0.6183 (2)	0.0243 (5)
H3	0.0686	0.2749	0.6853	0.029*
C4	0.16751 (15)	0.2639 (2)	0.5315 (2)	0.0269 (5)
H4	0.1771	0.1734	0.5382	0.032*
C5	0.21760 (14)	0.3364 (2)	0.4357 (2)	0.0236 (5)
H5	0.2601	0.2941	0.3746	0.028*
C6	0.20754 (13)	0.4707 (2)	0.4259 (2)	0.0185 (4)
C7	0.10934 (13)	0.7448 (2)	0.6095 (2)	0.0187 (4)
C8	0.08548 (16)	0.8812 (2)	0.5694 (2)	0.0257 (5)
H8A	0.1255	0.9410	0.6216	0.038*
H8B	0.0213	0.8985	0.5941	0.038*
H8C	0.0941	0.8931	0.4665	0.038*
C9	0.26855 (14)	0.5474 (2)	0.3343 (2)	0.0208 (5)
H9	0.2507	0.6338	0.3145	0.025*
C10	0.34701 (14)	0.5057 (2)	0.2767 (2)	0.0222 (5)
H10	0.3623	0.4177	0.2919	0.027*
C11	0.41182 (14)	0.5822 (2)	0.1925 (2)	0.0206 (5)
C12	0.38525 (15)	0.6915 (2)	0.1148 (2)	0.0242 (5)
H12	0.3230	0.7191	0.1156	0.029*
C13	0.45036 (16)	0.7595 (2)	0.0361 (2)	0.0261 (5)
H13	0.4322	0.8334	−0.0168	0.031*
C14	0.54070 (15)	0.7208 (2)	0.0343 (2)	0.0223 (5)
H14	0.5844	0.7671	−0.0208	0.027*
C15	0.56799 (14)	0.6138 (2)	0.1129 (2)	0.0218 (5)
C16	0.50366 (14)	0.5444 (2)	0.1902 (2)	0.0212 (5)
H16	0.5224	0.4701	0.2421	0.025*
C17	0.69172 (16)	0.4821 (2)	0.1966 (2)	0.0302 (5)
H17A	0.7586	0.4749	0.1882	0.045*
H17B	0.6631	0.4005	0.1677	0.045*
H17C	0.6755	0.5012	0.2959	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0362 (9)	0.0232 (8)	0.0144 (7)	0.0009 (7)	0.0007 (6)	−0.0012 (6)
O2	0.0182 (8)	0.0272 (9)	0.0366 (9)	−0.0019 (6)	0.0023 (6)	0.0044 (7)
N1	0.0207 (9)	0.0181 (9)	0.0144 (8)	0.0017 (7)	0.0011 (7)	0.0019 (7)
C1	0.0157 (10)	0.0204 (11)	0.0156 (9)	0.0000 (8)	−0.0024 (8)	−0.0020 (8)
C2	0.0162 (10)	0.0245 (11)	0.0203 (10)	0.0016 (9)	0.0011 (8)	0.0000 (9)
C3	0.0232 (12)	0.0231 (12)	0.0266 (11)	−0.0028 (9)	0.0005 (9)	0.0043 (9)
C4	0.0252 (12)	0.0170 (11)	0.0387 (13)	−0.0006 (9)	−0.0006 (10)	−0.0002 (10)
C5	0.0186 (11)	0.0227 (12)	0.0296 (11)	0.0013 (9)	0.0017 (9)	−0.0028 (10)
C6	0.0150 (10)	0.0210 (11)	0.0195 (10)	−0.0009 (8)	−0.0022 (8)	−0.0026 (9)
C7	0.0150 (10)	0.0214 (11)	0.0196 (10)	−0.0007 (8)	0.0010 (8)	−0.0007 (8)
C8	0.0349 (13)	0.0208 (12)	0.0213 (10)	0.0048 (9)	0.0023 (9)	−0.0014 (9)
C9	0.0212 (11)	0.0190 (11)	0.0220 (10)	0.0008 (9)	−0.0011 (8)	−0.0008 (9)
C10	0.0247 (12)	0.0197 (11)	0.0222 (10)	0.0001 (9)	0.0010 (9)	−0.0009 (9)
C11	0.0225 (11)	0.0233 (11)	0.0160 (9)	−0.0030 (9)	0.0018 (8)	−0.0051 (9)
C12	0.0220 (11)	0.0268 (12)	0.0238 (11)	0.0020 (9)	−0.0007 (9)	−0.0017 (10)
C13	0.0313 (13)	0.0237 (12)	0.0234 (11)	−0.0005 (10)	−0.0024 (9)	0.0028 (9)
C14	0.0241 (12)	0.0215 (11)	0.0213 (10)	−0.0055 (9)	0.0013 (8)	0.0016 (9)
C15	0.0182 (11)	0.0254 (12)	0.0218 (10)	−0.0016 (9)	−0.0005 (8)	−0.0055 (9)
C16	0.0238 (11)	0.0194 (11)	0.0203 (10)	0.0004 (9)	−0.0001 (8)	−0.0007 (9)
C17	0.0205 (12)	0.0338 (14)	0.0361 (13)	−0.0009 (10)	−0.0031 (10)	0.0052 (11)

Geometric parameters (Å, º) top

O1—C7	1.231 (2)	C8—H8B	0.9800
O2—C15	1.373 (2)	C8—H8C	0.9800
O2—C17	1.424 (3)	C9—C10	1.336 (3)
N1—C7	1.346 (3)	C9—H9	0.9500
N1—C1	1.426 (3)	C10—C11	1.464 (3)
N1—H1	0.877 (10)	C10—H10	0.9500
C1—C2	1.391 (3)	C11—C16	1.394 (3)
C1—C6	1.405 (3)	C11—C12	1.400 (3)
C2—C3	1.376 (3)	C12—C13	1.393 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.393 (3)	C13—C14	1.375 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.380 (3)	C14—C15	1.388 (3)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.402 (3)	C15—C16	1.386 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C9	1.470 (3)	C17—H17A	0.9800
C7—C8	1.504 (3)	C17—H17B	0.9800
C8—H8A	0.9800	C17—H17C	0.9800

C15—O2—C17	117.48 (17)	C10—C9—C6	125.4 (2)
C7—N1—C1	125.17 (17)	C10—C9—H9	117.3
C7—N1—H1	114.4 (16)	C6—C9—H9	117.3
C1—N1—H1	120.2 (16)	C9—C10—C11	126.5 (2)
C2—C1—C6	120.73 (19)	C9—C10—H10	116.7
C2—C1—N1	120.06 (18)	C11—C10—H10	116.7
C6—C1—N1	119.19 (18)	C16—C11—C12	118.93 (19)
C3—C2—C1	120.6 (2)	C16—C11—C10	118.36 (19)
C3—C2—H2	119.7	C12—C11—C10	122.71 (19)
C1—C2—H2	119.7	C13—C12—C11	119.8 (2)
C2—C3—C4	119.8 (2)	C13—C12—H12	120.1
C2—C3—H3	120.1	C11—C12—H12	120.1
C4—C3—H3	120.1	C14—C13—C12	120.7 (2)
C5—C4—C3	119.6 (2)	C14—C13—H13	119.6
C5—C4—H4	120.2	C12—C13—H13	119.6
C3—C4—H4	120.2	C13—C14—C15	119.9 (2)
C4—C5—C6	121.8 (2)	C13—C14—H14	120.0
C4—C5—H5	119.1	C15—C14—H14	120.0
C6—C5—H5	119.1	O2—C15—C16	124.12 (19)
C5—C6—C1	117.31 (19)	O2—C15—C14	115.96 (18)
C5—C6—C9	120.78 (19)	C16—C15—C14	119.9 (2)
C1—C6—C9	121.83 (19)	C15—C16—C11	120.7 (2)
O1—C7—N1	122.77 (19)	C15—C16—H16	119.6
O1—C7—C8	121.59 (18)	C11—C16—H16	119.6
N1—C7—C8	115.64 (17)	O2—C17—H17A	109.5
C7—C8—H8A	109.5	O2—C17—H17B	109.5
C7—C8—H8B	109.5	H17A—C17—H17B	109.5
H8A—C8—H8B	109.5	O2—C17—H17C	109.5
C7—C8—H8C	109.5	H17A—C17—H17C	109.5
H8A—C8—H8C	109.5	H17B—C17—H17C	109.5
H8B—C8—H8C	109.5

C7—N1—C1—C2	42.6 (3)	C1—C6—C9—C10	162.9 (2)
C7—N1—C1—C6	−138.9 (2)	C6—C9—C10—C11	−175.99 (18)
C6—C1—C2—C3	0.5 (3)	C9—C10—C11—C16	154.0 (2)
N1—C1—C2—C3	178.97 (18)	C9—C10—C11—C12	−25.9 (3)
C1—C2—C3—C4	−2.0 (3)	C16—C11—C12—C13	0.5 (3)
C2—C3—C4—C5	0.7 (3)	C10—C11—C12—C13	−179.63 (19)
C3—C4—C5—C6	2.1 (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—C9	173.33 (19)	C17—O2—C15—C16	−6.6 (3)
C2—C1—C6—C5	2.2 (3)	C17—O2—C15—C14	174.07 (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—C16	1.7 (3)
N1—C1—C6—C9	6.9 (3)	O2—C15—C16—C11	179.34 (19)
C1—N1—C7—O1	4.4 (3)	C14—C15—C16—C11	−1.4 (3)
C1—N1—C7—C8	−174.86 (18)	C12—C11—C16—C15	0.3 (3)
C5—C6—C9—C10	−13.8 (3)	C10—C11—C16—C15	−179.58 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88 (1)	1.93 (1)	2.804 (2)	175 (2)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₂
M_r	267.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.5588 (5), 10.3633 (4), 9.3667 (3)
β (°)	90.118 (1)
V (Å³)	1413.22 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.21 × 0.07 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12919, 3236, 2036
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.140, 1.01
No. of reflections	3236
No. of parameters	187
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.25

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88 (1)	1.93 (1)	2.804 (2)	175 (2)

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

We thank the University of Malaya for supporting this study.

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. Web of Science CrossRef CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar