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

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

doi:10.1107/S1600536809017395

organic compounds

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Volume 65| Part 6| June 2009| Page o1289

doi:10.1107/S1600536809017395

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

Kartini Ahmad,^a Noel F. Thomas,^a Mohd Fadzli Din,^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 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 ).

Experimental

Crystal data

C₁₇H₁₇NO₂
M_r = 267.32
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.096
S = 1.05
1654 reflections
187 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 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)	2.03 (1)	2.895 (2)	169 (2)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (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/S1600536809017395/hg2513sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017395/hg2513Isup2.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 (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-(4-Methoxyphenyl)ethenyl]phenyl}acetamide top

Crystal data top

C₁₇H₁₇NO₂	F(000) = 284
M_r = 267.32	D_x = 1.295 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3188 reflections
a = 5.4225 (1) Å	θ = 2.6–28.3°
b = 9.4222 (2) Å	µ = 0.09 mm⁻¹
c = 13.5653 (3) Å	T = 100 K
β = 98.402 (1)°	Block, colorless
V = 685.64 (2) Å³	0.25 × 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 tube	R_int = 0.016
Graphite monochromator	θ_max = 27.5°, θ_min = 1.5°
ω scans	h = −7→6
4781 measured reflections	k = −11→12
1654 independent reflections	l = −17→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0726P)² + 0.080P] where P = (F_o² + 2F_c²)/3
1654 reflections	(Δ/σ)_max = 0.001
187 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₇H₁₇NO₂	V = 685.64 (2) Å³
M_r = 267.32	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.4225 (1) Å	µ = 0.09 mm⁻¹
b = 9.4222 (2) Å	T = 100 K
c = 13.5653 (3) Å	0.25 × 0.20 × 0.20 mm
β = 98.402 (1)°

Data collection top

Bruker SMART APEX diffractometer	1605 reflections with I > 2σ(I)
4781 measured reflections	R_int = 0.016
1654 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	2 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.25 e Å⁻³
1654 reflections	Δρ_min = −0.22 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	0.5611 (2)	−0.00004 (14)	0.48762 (9)	0.0210 (3)
O2	0.0298 (2)	0.84291 (14)	0.93515 (9)	0.0198 (3)
N1	0.6516 (3)	0.22034 (16)	0.55197 (10)	0.0142 (3)
H1	0.597 (4)	0.3083 (13)	0.5476 (17)	0.021 (6)*
C1	0.8511 (3)	0.18307 (17)	0.62796 (11)	0.0137 (3)
C2	1.0223 (3)	0.07880 (19)	0.60968 (12)	0.0167 (3)
H2	0.9996	0.0294	0.5480	0.020*
C3	1.2247 (3)	0.0471 (2)	0.68092 (13)	0.0178 (3)
H3	1.3400	−0.0242	0.6683	0.021*
C4	1.2586 (3)	0.12030 (19)	0.77122 (13)	0.0186 (4)
H4	1.3989	0.1001	0.8198	0.022*
C5	1.0881 (3)	0.22226 (19)	0.79020 (12)	0.0163 (3)
H5	1.1130	0.2709	0.8522	0.020*
C6	0.8790 (3)	0.25582 (17)	0.72004 (12)	0.0134 (3)
C7	0.5199 (3)	0.12874 (19)	0.48755 (12)	0.0154 (3)
C8	0.3184 (3)	0.1947 (2)	0.41365 (12)	0.0197 (4)
H8A	0.1965	0.1219	0.3881	0.030*
H8B	0.3925	0.2354	0.3583	0.030*
H8C	0.2351	0.2697	0.4465	0.030*
C9	0.6925 (3)	0.36010 (18)	0.74194 (12)	0.0138 (3)
H9	0.5492	0.3725	0.6934	0.017*
C10	0.7082 (3)	0.43902 (18)	0.82474 (12)	0.0139 (3)
H10	0.8543	0.4281	0.8721	0.017*
C11	0.5219 (3)	0.54060 (17)	0.84945 (12)	0.0133 (3)
C12	0.3218 (3)	0.58920 (19)	0.78032 (12)	0.0167 (3)
H12	0.2993	0.5521	0.7145	0.020*
C13	0.1558 (3)	0.6903 (2)	0.80590 (12)	0.0176 (4)
H13	0.0238	0.7230	0.7574	0.021*
C14	0.1830 (3)	0.74359 (17)	0.90263 (13)	0.0159 (3)
C15	0.3793 (3)	0.6960 (2)	0.97288 (12)	0.0174 (3)
H15	0.3988	0.7316	1.0391	0.021*
C16	0.5455 (3)	0.59685 (19)	0.94598 (12)	0.0166 (3)
H16	0.6794	0.5661	0.9943	0.020*
C17	−0.1752 (3)	0.8937 (2)	0.86533 (13)	0.0195 (4)
H17A	−0.2719	0.9622	0.8983	0.029*
H17B	−0.2822	0.8138	0.8405	0.029*
H17C	−0.1116	0.9399	0.8094	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0263 (7)	0.0130 (6)	0.0215 (6)	0.0003 (5)	−0.0038 (5)	−0.0027 (5)
O2	0.0180 (6)	0.0207 (7)	0.0199 (6)	0.0059 (5)	0.0003 (4)	−0.0056 (5)
N1	0.0181 (7)	0.0110 (6)	0.0128 (6)	0.0011 (5)	−0.0004 (5)	−0.0001 (5)
C1	0.0146 (7)	0.0124 (8)	0.0138 (7)	−0.0028 (6)	0.0010 (6)	0.0009 (6)
C2	0.0195 (8)	0.0147 (8)	0.0164 (7)	−0.0003 (6)	0.0038 (6)	−0.0019 (6)
C3	0.0163 (7)	0.0163 (8)	0.0214 (8)	0.0033 (7)	0.0051 (6)	0.0014 (7)
C4	0.0145 (7)	0.0181 (8)	0.0221 (8)	0.0011 (7)	−0.0005 (6)	0.0026 (7)
C5	0.0171 (8)	0.0165 (8)	0.0146 (7)	−0.0010 (7)	−0.0002 (6)	−0.0011 (6)
C6	0.0157 (8)	0.0107 (7)	0.0139 (7)	−0.0019 (6)	0.0019 (6)	0.0002 (6)
C7	0.0191 (8)	0.0149 (9)	0.0122 (7)	−0.0011 (6)	0.0021 (6)	−0.0003 (6)
C8	0.0239 (8)	0.0181 (9)	0.0151 (8)	0.0006 (7)	−0.0042 (6)	0.0003 (6)
C9	0.0142 (7)	0.0131 (7)	0.0135 (7)	0.0001 (6)	−0.0003 (5)	0.0003 (6)
C10	0.0160 (7)	0.0115 (7)	0.0139 (7)	0.0002 (6)	0.0014 (5)	0.0020 (6)
C11	0.0153 (7)	0.0108 (8)	0.0140 (7)	−0.0011 (6)	0.0028 (6)	0.0006 (6)
C12	0.0191 (8)	0.0164 (8)	0.0137 (7)	−0.0003 (7)	−0.0004 (6)	−0.0031 (6)
C13	0.0155 (8)	0.0186 (9)	0.0173 (8)	0.0007 (7)	−0.0020 (6)	−0.0021 (7)
C14	0.0151 (7)	0.0126 (8)	0.0203 (8)	−0.0001 (6)	0.0032 (6)	−0.0010 (6)
C15	0.0225 (8)	0.0174 (8)	0.0121 (7)	0.0011 (7)	0.0022 (6)	−0.0019 (6)
C16	0.0194 (8)	0.0161 (8)	0.0134 (7)	0.0015 (7)	−0.0008 (6)	0.0008 (6)
C17	0.0165 (8)	0.0179 (8)	0.0236 (8)	0.0030 (7)	0.0012 (6)	0.0005 (7)

Geometric parameters (Å, º) top

O1—C7	1.234 (2)	C8—H8B	0.9800
O2—C14	1.367 (2)	C8—H8C	0.9800
O2—C17	1.433 (2)	C9—C10	1.339 (2)
N1—C7	1.355 (2)	C9—H9	0.9500
N1—C1	1.425 (2)	C10—C11	1.465 (2)
N1—H1	0.879 (10)	C10—H10	0.9500
C1—C2	1.398 (2)	C11—C16	1.401 (2)
C1—C6	1.413 (2)	C11—C12	1.403 (2)
C2—C3	1.385 (2)	C12—C13	1.389 (2)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.394 (3)	C13—C14	1.393 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.383 (2)	C14—C15	1.395 (2)
C4—H4	0.9500	C15—C16	1.384 (2)
C5—C6	1.406 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C6—C9	1.471 (2)	C17—H17A	0.9800
C7—C8	1.505 (2)	C17—H17B	0.9800
C8—H8A	0.9800	C17—H17C	0.9800

C14—O2—C17	117.70 (13)	C10—C9—C6	125.37 (14)
C7—N1—C1	125.62 (15)	C10—C9—H9	117.3
C7—N1—H1	114.7 (15)	C6—C9—H9	117.3
C1—N1—H1	119.5 (15)	C9—C10—C11	126.38 (15)
C2—C1—C6	120.61 (15)	C9—C10—H10	116.8
C2—C1—N1	119.89 (14)	C11—C10—H10	116.8
C6—C1—N1	119.45 (14)	C16—C11—C12	117.21 (15)
C3—C2—C1	120.45 (15)	C16—C11—C10	119.28 (15)
C3—C2—H2	119.8	C12—C11—C10	123.48 (14)
C1—C2—H2	119.8	C13—C12—C11	121.52 (15)
C2—C3—C4	119.71 (16)	C13—C12—H12	119.2
C2—C3—H3	120.1	C11—C12—H12	119.2
C4—C3—H3	120.1	C12—C13—C14	119.98 (15)
C5—C4—C3	120.08 (16)	C12—C13—H13	120.0
C5—C4—H4	120.0	C14—C13—H13	120.0
C3—C4—H4	120.0	O2—C14—C13	124.45 (15)
C4—C5—C6	121.68 (15)	O2—C14—C15	116.02 (14)
C4—C5—H5	119.2	C13—C14—C15	119.53 (15)
C6—C5—H5	119.2	C16—C15—C14	119.89 (15)
C5—C6—C1	117.44 (15)	C16—C15—H15	120.1
C5—C6—C9	121.59 (14)	C14—C15—H15	120.1
C1—C6—C9	120.95 (14)	C15—C16—C11	121.86 (15)
O1—C7—N1	123.22 (16)	C15—C16—H16	119.1
O1—C7—C8	121.35 (16)	C11—C16—H16	119.1
N1—C7—C8	115.43 (16)	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	38.5 (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—C16	169.14 (16)
N1—C1—C2—C3	176.45 (14)	C9—C10—C11—C12	−12.9 (3)
C1—C2—C3—C4	−0.4 (3)	C16—C11—C12—C13	0.9 (2)
C2—C3—C4—C5	1.2 (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—C13	1.1 (2)
C4—C5—C6—C9	177.47 (16)	C17—O2—C14—C15	−179.56 (15)
C2—C1—C6—C5	2.0 (2)	C12—C13—C14—O2	−179.96 (16)
N1—C1—C6—C5	−175.74 (15)	C12—C13—C14—C15	0.8 (3)
C2—C1—C6—C9	−176.66 (14)	O2—C14—C15—C16	−179.11 (15)
N1—C1—C6—C9	5.6 (2)	C13—C14—C15—C16	0.2 (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—C15	0.1 (2)
C5—C6—C9—C10	4.8 (3)	C10—C11—C16—C15	178.23 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88 (1)	2.03 (1)	2.895 (2)	169 (2)

Symmetry code: (i) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₂
M_r	267.32
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	5.4225 (1), 9.4222 (2), 13.5653 (3)
β (°)	98.402 (1)
V (Å³)	685.64 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4781, 1654, 1605
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.096, 1.05
No. of reflections	1654
No. of parameters	187
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: APEX2 (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)	2.03 (1)	2.895 (2)	169 (2)

Symmetry code: (i) −x+1, y+1/2, −z+1.

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
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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