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organic compounds
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
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
|
Data collection: APEX2 (Bruker, 2007); cell 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
10.1107/S1600536809003250/tk2361sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809003250/tk2361Isup2.hkl
Carbon-bound H atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the
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)).Data collection: APEX2 (Bruker, 2007); cell
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). ![]() | Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C18H17Cl2NO3 at the 70% probability level. H atoms are drawn as spheres of arbitrary radius. |
C18H17Cl2NO3 | Z = 2 |
Mr = 366.23 | F(000) = 380 |
Triclinic, P1 | Dx = 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 |
Bruker SMART APEX diffractometer | 3657 independent reflections |
Radiation source: fine-focus sealed tube | 2490 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.886, Tmax = 0.988 | k = −11→11 |
6677 measured reflections | l = −15→15 |
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(Fo2) + (0.046P)2] where P = (Fo2 + 2Fc2)/3 |
3657 reflections | (Δ/σ)max = 0.001 |
220 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C18H17Cl2NO3 | γ = 85.969 (3)° |
Mr = 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)° |
Bruker SMART APEX diffractometer | 3657 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2490 reflections with I > 2σ(I) |
Tmin = 0.886, Tmax = 0.988 | Rint = 0.048 |
6677 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.40 e Å−3 |
3657 reflections | Δρmin = −0.37 e Å−3 |
220 parameters |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.886, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6677, 3657, 2490 |
Rint | 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 |
Δρmax, Δρmin (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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Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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
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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).