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

Ahmad, K.; Awang, K.; Thomas, N.F.; Weber, J.-F.F.; Ng, S.W.

doi:10.1107/S1600536809003250

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o438

doi:10.1107/S1600536809003250

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

Kartini Ahmad,^a Khalijah Awang,^a Noel F. Thomas,^a Jean-Frederic Faizal Weber ^b and Seik Weng Ng ^a ^*

^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 ).

Experimental

Crystal data

C₁₈H₁₇Cl₂NO₃
M_r = 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 ) T_min = 0.886, T_max = 0.988
6677 measured reflections
3657 independent reflections
2490 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.117
S = 0.99
3657 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536809003250/tk2361sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003250/tk2361Isup2.hkl

checkCIF report

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

Experimental top

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

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

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

C₁₈H₁₇Cl₂NO₃	Z = 2
M_r = 366.23	F(000) = 380
Triclinic, P1	D_x = 1.493 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5646 (3) Å	Cell parameters from 1123 reflections
b = 9.1485 (3) Å	θ = 2.6–26.5°
c = 12.2969 (5) Å	µ = 0.42 mm⁻¹
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 tube	2490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.886, T_max = 0.988	k = −11→11
6677 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.046P)²] where P = (F_o² + 2F_c²)/3
3657 reflections	(Δ/σ)_max = 0.001
220 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₈H₁₇Cl₂NO₃	γ = 85.969 (3)°
M_r = 366.23	V = 814.65 (5) Å³
Triclinic, P1	Z = 2
a = 7.5646 (3) Å	Mo Kα radiation
b = 9.1485 (3) Å	µ = 0.42 mm⁻¹
c = 12.2969 (5) Å	T = 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)
T_min = 0.886, T_max = 0.988	R_int = 0.048
6677 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 0.99	Δρ_max = 0.40 e Å⁻³
3657 reflections	Δρ_min = −0.37 e Å⁻³
220 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.21992 (9)	0.40664 (7)	0.21221 (5)	0.02175 (18)
Cl2	0.28411 (9)	0.66314 (7)	0.56854 (5)	0.01944 (18)
O1	0.3311 (3)	0.68767 (19)	0.08280 (14)	0.0248 (5)
O2	0.4014 (2)	0.90427 (18)	0.39962 (15)	0.0203 (4)
O3	0.1911 (3)	0.2547 (2)	0.96831 (17)	0.0353 (5)
N1	0.1666 (3)	0.3365 (2)	0.78526 (18)	0.0198 (5)
H1	0.1734	0.4173	0.7322	0.024*
C1	0.2581 (3)	0.5380 (3)	0.3861 (2)	0.0141 (5)
C2	0.2725 (3)	0.5540 (3)	0.2691 (2)	0.0162 (6)
C3	0.3281 (4)	0.6856 (3)	0.1940 (2)	0.0171 (6)
C4	0.3763 (4)	0.8042 (3)	0.2354 (2)	0.0183 (6)
H4	0.4190	0.8928	0.1845	0.022*
C5	0.3624 (3)	0.7936 (3)	0.3506 (2)	0.0158 (6)
C6	0.3045 (3)	0.6611 (3)	0.4245 (2)	0.0149 (5)
C7	0.3852 (4)	0.8217 (3)	0.0026 (2)	0.0285 (7)
H7A	0.3723	0.8102	−0.0729	0.043*
H7B	0.5119	0.8405	0.0009	0.043*
H7C	0.3085	0.9060	0.0250	0.043*
C8	0.4638 (4)	1.0415 (3)	0.3273 (2)	0.0232 (6)
H8A	0.4852	1.1118	0.3735	0.035*
H8B	0.3721	1.0843	0.2836	0.035*
H8C	0.5768	1.0225	0.2753	0.035*
C9	0.1833 (3)	0.4005 (3)	0.4615 (2)	0.0154 (6)
H9	0.0883	0.3559	0.4413	0.019*
C10	0.2381 (3)	0.3337 (3)	0.5558 (2)	0.0144 (5)
H10	0.3401	0.3734	0.5723	0.017*
C11	0.1548 (3)	0.2039 (3)	0.6366 (2)	0.0159 (6)
C12	0.1058 (4)	0.0794 (3)	0.6023 (2)	0.0193 (6)
H12	0.1223	0.0778	0.5238	0.023*
C13	0.0330 (4)	−0.0426 (3)	0.6812 (2)	0.0207 (6)
H13	−0.0016	−0.1264	0.6565	0.025*
C14	0.0106 (4)	−0.0427 (3)	0.7955 (2)	0.0222 (6)
H14	−0.0367	−0.1275	0.8492	0.027*
C15	0.0568 (4)	0.0805 (3)	0.8323 (2)	0.0203 (6)
H15	0.0404	0.0803	0.9111	0.024*
C16	0.1273 (4)	0.2042 (3)	0.7536 (2)	0.0178 (6)
C17	0.1954 (4)	0.3555 (3)	0.8874 (2)	0.0234 (6)
C18	0.2350 (4)	0.5142 (3)	0.8907 (2)	0.0289 (7)
H18A	0.2924	0.5147	0.9549	0.043*
H18B	0.1216	0.5736	0.8993	0.043*
H18C	0.3165	0.5572	0.8201	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0352 (4)	0.0150 (3)	0.0164 (3)	−0.0059 (3)	−0.0067 (3)	−0.0029 (3)
Cl2	0.0257 (4)	0.0188 (3)	0.0144 (3)	−0.0049 (3)	−0.0029 (3)	−0.0043 (3)
O1	0.0446 (13)	0.0180 (10)	0.0117 (9)	−0.0104 (9)	−0.0079 (9)	0.0034 (8)
O2	0.0262 (11)	0.0149 (9)	0.0198 (10)	−0.0069 (8)	−0.0029 (8)	−0.0033 (8)
O3	0.0505 (14)	0.0387 (12)	0.0172 (11)	−0.0163 (11)	−0.0106 (10)	0.0027 (10)
N1	0.0279 (13)	0.0169 (11)	0.0133 (11)	−0.0032 (10)	−0.0023 (10)	−0.0004 (9)
C1	0.0100 (12)	0.0137 (12)	0.0179 (13)	0.0009 (9)	−0.0022 (10)	−0.0028 (10)
C2	0.0182 (14)	0.0156 (12)	0.0161 (13)	−0.0017 (10)	−0.0053 (11)	−0.0039 (11)
C3	0.0192 (14)	0.0166 (13)	0.0153 (13)	−0.0008 (11)	−0.0042 (11)	−0.0015 (11)
C4	0.0227 (15)	0.0133 (12)	0.0166 (14)	−0.0038 (11)	−0.0019 (11)	0.0016 (11)
C5	0.0157 (13)	0.0139 (12)	0.0192 (14)	0.0007 (10)	−0.0047 (11)	−0.0056 (11)
C6	0.0151 (13)	0.0183 (13)	0.0103 (12)	0.0009 (10)	−0.0016 (10)	−0.0019 (10)
C7	0.0440 (19)	0.0234 (15)	0.0151 (14)	−0.0083 (14)	−0.0060 (13)	0.0057 (12)
C8	0.0253 (16)	0.0149 (13)	0.0282 (16)	−0.0048 (11)	−0.0065 (13)	0.0012 (12)
C9	0.0195 (14)	0.0121 (12)	0.0149 (13)	−0.0008 (10)	−0.0027 (11)	−0.0037 (10)
C10	0.0153 (13)	0.0119 (12)	0.0158 (13)	−0.0029 (10)	−0.0005 (11)	−0.0038 (10)
C11	0.0165 (14)	0.0148 (13)	0.0150 (13)	0.0008 (10)	−0.0046 (11)	0.0016 (11)
C12	0.0195 (14)	0.0192 (13)	0.0183 (14)	0.0020 (11)	−0.0042 (11)	−0.0020 (11)
C13	0.0213 (15)	0.0108 (12)	0.0285 (16)	−0.0014 (11)	−0.0034 (12)	−0.0020 (11)
C14	0.0211 (15)	0.0190 (14)	0.0223 (15)	−0.0022 (11)	−0.0023 (12)	0.0046 (12)
C15	0.0213 (15)	0.0217 (14)	0.0147 (13)	0.0006 (11)	−0.0008 (11)	0.0008 (11)
C16	0.0182 (14)	0.0175 (13)	0.0178 (14)	0.0016 (11)	−0.0043 (11)	−0.0040 (11)
C17	0.0220 (15)	0.0321 (16)	0.0155 (14)	−0.0029 (13)	−0.0018 (12)	−0.0046 (13)
C18	0.0397 (19)	0.0290 (16)	0.0211 (15)	−0.0074 (14)	−0.0058 (14)	−0.0105 (13)

Geometric parameters (Å, º) top

Cl1—C2	1.742 (2)	C8—H8A	0.9800
Cl2—C6	1.748 (2)	C8—H8B	0.9800
O1—C3	1.359 (3)	C8—H8C	0.9800
O1—C7	1.437 (3)	C9—C10	1.333 (4)
O2—C5	1.355 (3)	C9—H9	0.9500
O2—C8	1.433 (3)	C10—C11	1.471 (3)
O3—C17	1.211 (3)	C10—H10	0.9500
N1—C17	1.365 (3)	C11—C12	1.389 (3)
N1—C16	1.411 (3)	C11—C16	1.410 (3)
N1—H1	0.8800	C12—C13	1.386 (4)
C1—C6	1.397 (3)	C12—H12	0.9500
C1—C2	1.399 (3)	C13—C14	1.379 (4)
C1—C9	1.476 (3)	C13—H13	0.9500
C2—C3	1.395 (3)	C14—C15	1.386 (4)
C3—C4	1.387 (3)	C14—H14	0.9500
C4—C5	1.382 (3)	C15—C16	1.391 (4)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.398 (3)	C17—C18	1.513 (4)
C7—H7A	0.9800	C18—H18A	0.9800
C7—H7B	0.9800	C18—H18B	0.9800
C7—H7C	0.9800	C18—H18C	0.9800

C3—O1—C7	118.2 (2)	H8B—C8—H8C	109.5
C5—O2—C8	118.00 (19)	C10—C9—C1	125.3 (2)
C17—N1—C16	128.5 (2)	C10—C9—H9	117.3
C17—N1—H1	115.7	C1—C9—H9	117.3
C16—N1—H1	115.7	C9—C10—C11	125.8 (2)
C6—C1—C2	116.4 (2)	C9—C10—H10	117.1
C6—C1—C9	124.0 (2)	C11—C10—H10	117.1
C2—C1—C9	119.5 (2)	C12—C11—C16	118.6 (2)
C3—C2—C1	122.4 (2)	C12—C11—C10	122.6 (2)
C3—C2—Cl1	117.50 (19)	C16—C11—C10	118.8 (2)
C1—C2—Cl1	120.11 (19)	C13—C12—C11	120.9 (2)
O1—C3—C4	124.3 (2)	C13—C12—H12	119.6
O1—C3—C2	116.4 (2)	C11—C12—H12	119.6
C4—C3—C2	119.4 (2)	C14—C13—C12	120.1 (2)
C5—C4—C3	120.1 (2)	C14—C13—H13	119.9
C5—C4—H4	120.0	C12—C13—H13	119.9
C3—C4—H4	120.0	C13—C14—C15	120.3 (2)
O2—C5—C4	124.6 (2)	C13—C14—H14	119.8
O2—C5—C6	115.8 (2)	C15—C14—H14	119.8
C4—C5—C6	119.6 (2)	C14—C15—C16	119.8 (2)
C5—C6—C1	122.2 (2)	C14—C15—H15	120.1
C5—C6—Cl2	115.48 (18)	C16—C15—H15	120.1
C1—C6—Cl2	122.29 (19)	C15—C16—N1	122.6 (2)
O1—C7—H7A	109.5	C15—C16—C11	120.3 (2)
O1—C7—H7B	109.5	N1—C16—C11	117.0 (2)
H7A—C7—H7B	109.5	O3—C17—N1	123.4 (3)
O1—C7—H7C	109.5	O3—C17—C18	122.7 (3)
H7A—C7—H7C	109.5	N1—C17—C18	114.0 (2)
H7B—C7—H7C	109.5	C17—C18—H18A	109.5
O2—C8—H8A	109.5	C17—C18—H18B	109.5
O2—C8—H8B	109.5	H18A—C18—H18B	109.5
H8A—C8—H8B	109.5	C17—C18—H18C	109.5
O2—C8—H8C	109.5	H18A—C18—H18C	109.5
H8A—C8—H8C	109.5	H18B—C18—H18C	109.5

C6—C1—C2—C3	−0.7 (4)	C2—C1—C6—Cl2	176.94 (19)
C9—C1—C2—C3	174.7 (2)	C9—C1—C6—Cl2	1.8 (4)
C6—C1—C2—Cl1	179.43 (19)	C6—C1—C9—C10	−40.8 (4)
C9—C1—C2—Cl1	−5.2 (3)	C2—C1—C9—C10	144.2 (3)
C7—O1—C3—C4	−0.9 (4)	C1—C9—C10—C11	174.6 (2)
C7—O1—C3—C2	179.2 (2)	C9—C10—C11—C12	45.5 (4)
C1—C2—C3—O1	−178.1 (2)	C9—C10—C11—C16	−136.0 (3)
Cl1—C2—C3—O1	1.8 (3)	C16—C11—C12—C13	−0.6 (4)
C1—C2—C3—C4	2.0 (4)	C10—C11—C12—C13	177.9 (2)
Cl1—C2—C3—C4	−178.1 (2)	C11—C12—C13—C14	−0.9 (4)
O1—C3—C4—C5	177.6 (2)	C12—C13—C14—C15	1.5 (4)
C2—C3—C4—C5	−2.5 (4)	C13—C14—C15—C16	−0.5 (4)
C8—O2—C5—C4	−0.8 (4)	C14—C15—C16—N1	176.0 (2)
C8—O2—C5—C6	179.1 (2)	C14—C15—C16—C11	−1.1 (4)
C3—C4—C5—O2	−178.2 (2)	C17—N1—C16—C15	20.7 (4)
C3—C4—C5—C6	1.9 (4)	C17—N1—C16—C11	−162.1 (3)
O2—C5—C6—C1	179.5 (2)	C12—C11—C16—C15	1.6 (4)
C4—C5—C6—C1	−0.6 (4)	C10—C11—C16—C15	−177.0 (2)
O2—C5—C6—Cl2	2.3 (3)	C12—C11—C16—N1	−175.6 (2)
C4—C5—C6—Cl2	−177.7 (2)	C10—C11—C16—N1	5.8 (4)
C2—C1—C6—C5	0.0 (4)	C16—N1—C17—O3	0.3 (5)
C9—C1—C6—C5	−175.1 (2)	C16—N1—C17—C18	179.8 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇Cl₂NO₃
M_r	366.23
Crystal system, space group	Triclinic, 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)
V (Å³)	814.65 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.30 × 0.03 × 0.03

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.886, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	6677, 3657, 2490
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.117, 0.99
No. of reflections	3657
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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. Web of Science CrossRef CAS Google Scholar
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