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ISSN: 2056-9890

N-(2-Methyl-3-oxo-1,3-di­phenyl­prop­yl)acetamide

aSchool of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
*Correspondence e-mail: jrli@bit.edu.cn

(Received 12 January 2013; accepted 17 March 2013; online 5 April 2013)

In the title compound, C18H19NO2, the dihedral angle between the benzene rings is 42.0 (1)°. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯π inter­actions.

Related literature

For the biological properties of N-(2-methyl-3-oxo-1,3-diphenyl­prop­yl)acetamide derivatives, see: Barluenga et al. (1993[Barluenga, J., Viado, A., Aguilar, E., Fustero, S. & Olano, B. (1993). J. Org. Chem. 58, 5972-5975.]); Casimir et al. (1995[Casimir, J. R., Turetta, C., Ettouati, L. & Pairs, J. (1995). Tetrahedron Lett. 36, 4797-4800.]) and for their synthesis, see: Dakin & West (1928[Dakin, H. D. & West, R. (1928). J. Biol. Chem. 78, 745-756.]); Selvam & Perumal (2009[Selvam, P. & Perumal, P. (2009). Arkivoc, x, 265-282.]); Heravi et al. (2009[Heravi, M. M., Behbahani, F. K., Daraie, M. & Oskooie, H. A. (2009). Mol. Divers. 13, 375-378.]).

[Scheme 1]

Experimental

Crystal data
  • C18H19NO2

  • Mr = 281.34

  • Monoclinic, P 21 /c

  • a = 9.156 (5) Å

  • b = 17.668 (8) Å

  • c = 10.103 (5) Å

  • β = 107.914 (7)°

  • V = 1555.0 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 153 K

  • 0.61 × 0.07 × 0.02 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.954, Tmax = 0.998

  • 12600 measured reflections

  • 3028 independent reflections

  • 2386 reflections with I > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.156

  • S = 1.00

  • 3028 reflections

  • 197 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C10–C15 and C1–C6 benzene rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O2i 0.94 (3) 1.98 (3) 2.874 (3) 158 (2)
C1—H1⋯Cg1i 0.95 2.85 (1) 3.649 (3) 142 (1)
C16—H16ACg2ii 0.98 2.98 (1) 3.472 (3) 112 (1)
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+1, y+{\script{3\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

N–(2–methyl–3–oxo–1,3–diphenylpropyl)acetamide is a class of 2–acetamino carbonyl compounds which exhibit great importance of biological (Casimir et al., 1995) and pharmacological (Barluenga et al., 1993) properties. Here, we report the crystal structure of the title compound. In the title molecule (Fig. 1), the dihedral angle formed by the benzene rings is 42.0°, and the methyl and the acetamide groups have an anti–conformation. In the crystal structure (Fig. 2), molecules are connected by N—H···O and C—H···π interactions (Table 1, Cg1 and Cg2 are the centroids of the C10–C15 benzene ring and the C1–C6 benzene ring, respectively).

Related literature top

For the biological properties of N-(2-methyl-3-oxo-1,3-diphenylpropyl)acetamide derivatives, see: Barluenga et al. (1993); Casimir et al. (1995) and for their synthesis, see: Dakin & West (1928); Selvam & Perumal (2009); Heravi et al. (2009).

Experimental top

A solution of benzaldehyde (2 mmol) and propiophenone (2 mmol) in the presence of acetyl chloride and TiCl4 was stirred in acetonitrile (5 ml) at room teperature for 3 h. The reaction mixture was poured to room temperature and then filtered to give the title compound. The product was recrystallizated from petrolum ether and ethyl acetate to give white crystalline powder. m.p. 439–441 K.

Refinement top

C—H were included in the riding model approximation with C—H distances 0.95–1.00 Å, and with Uiso(H)=1.2Ueq(C) or 1.5Ueq(C)(methyl). Freely refined H atoms of NH group were located in difference Fourrier maps with N—H distances 0.94 Å with Uiso(H)=1.5Ueq(N).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku/MSC, 2009); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of N—H···O and C—H···π interactions. (dotted lines) in the crystal structure of the title compound. H atoms non–participating in hydrogen–bonding were omitted for clarity. [Symmetry codes: (i) x, - y + 3/2, z - 1/2; (ii) - x + 1, - y + 1, - z + 1; (iii) x, - y + 3/2, z + 1/2.]
N-(2-Methyl-3-oxo-1,3-diphenylpropyl)acetamide top
Crystal data top
C18H19NO2F(000) = 600
Mr = 281.34Dx = 1.202 Mg m3
Monoclinic, P21/cMelting point = 439–441 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.156 (5) ÅCell parameters from 3372 reflections
b = 17.668 (8) Åθ = 2.3–29.0°
c = 10.103 (5) ŵ = 0.08 mm1
β = 107.914 (7)°T = 153 K
V = 1555.0 (13) Å3Prism, colorless
Z = 40.61 × 0.07 × 0.02 mm
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
3028 independent reflections
Radiation source: Rotating Anode2386 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 28.5714 pixels mm-1θmax = 26.0°, θmin = 2.3°
phi and ω scansh = 1111
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)
k = 2021
Tmin = 0.954, Tmax = 0.998l = 1212
12600 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.0511P)2 + 1.630P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3028 reflectionsΔρmax = 0.22 e Å3
197 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (2)
Crystal data top
C18H19NO2V = 1555.0 (13) Å3
Mr = 281.34Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.156 (5) ŵ = 0.08 mm1
b = 17.668 (8) ÅT = 153 K
c = 10.103 (5) Å0.61 × 0.07 × 0.02 mm
β = 107.914 (7)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
3028 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)
2386 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.998Rint = 0.050
12600 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.22 e Å3
3028 reflectionsΔρmin = 0.24 e Å3
197 parameters
Special details top

Experimental. Spectral data: IR (KBr): 3297, 3061, 2980, 1683, 1651, 1544, 1448, 1370, 1208, 1140, 970, 707, 615 cm-1; 1H–NMR(DMSO,p.p.m.):1.13 (3H, d, J = 6.8 Hz C1H3), 1.85 (3H, s, C1O1C1H3), 4.00–4.14 (1H, m, C1H1), 5.26 (1H, t, J = 11.6 Hz, C1H1), 7.12 (1H, t, J = 6.8 Hz, Benzene-H), 7.22 (2H, t, J = 8.0 Hz, Benzene-H), 7.29 (2H, d, J = 7.6 Hz, Benzene-H), 7.47 (2H, t, J = 8.0 Hz, Benzene-H), 7.58 (1H, t, J = 6.8 Hz, Benzene-H), 7.80 (2H, t, J = 7.6 Hz, Benzene-H), 8.30 (1H, d, J = 9.2 Hz, NH); ESI-MS m/z: [M+Na]+ 304.2.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2368 (2)0.56897 (11)0.6152 (2)0.0553 (6)
O20.13769 (19)0.74116 (10)0.76594 (17)0.0390 (4)
N10.1849 (2)0.74059 (11)0.5589 (2)0.0305 (5)
C10.2662 (3)0.55877 (14)0.2653 (3)0.0401 (6)
H10.33420.59980.26800.048*
C20.2150 (3)0.51473 (15)0.1457 (3)0.0483 (7)
H20.24900.52520.06770.058*
C30.1143 (3)0.45551 (16)0.1410 (3)0.0535 (8)
H30.07910.42550.05930.064*
C40.0646 (3)0.43978 (15)0.2540 (3)0.0520 (8)
H40.00550.39950.24970.062*
C50.1172 (3)0.48288 (15)0.3731 (3)0.0456 (7)
H50.08410.47140.45120.055*
C60.2190 (3)0.54355 (13)0.3808 (3)0.0373 (6)
C70.2732 (3)0.58798 (14)0.5128 (3)0.0384 (6)
C80.3799 (3)0.65579 (13)0.5217 (2)0.0324 (5)
H80.36260.67690.42630.039*
C90.3469 (3)0.71774 (13)0.6157 (2)0.0317 (5)
H90.36270.69560.71010.038*
C100.4548 (3)0.78490 (13)0.6304 (2)0.0327 (5)
C110.4362 (3)0.83580 (13)0.5211 (3)0.0369 (6)
H110.35460.82890.43720.044*
C120.5363 (3)0.89691 (15)0.5338 (3)0.0444 (7)
H120.52360.93080.45800.053*
C130.6541 (3)0.90834 (16)0.6565 (3)0.0472 (7)
H130.72090.95050.66560.057*
C140.6741 (3)0.85819 (16)0.7654 (3)0.0470 (7)
H140.75510.86570.84950.056*
C150.5756 (3)0.79640 (15)0.7523 (3)0.0400 (6)
H150.59100.76180.82730.048*
C160.5456 (3)0.62634 (15)0.5778 (3)0.0439 (6)
H16A0.56260.60440.67040.053*
H16B0.61740.66830.58380.053*
H16C0.56260.58750.51480.053*
C170.0921 (3)0.74884 (12)0.6372 (2)0.0304 (5)
C180.0729 (3)0.76761 (16)0.5617 (3)0.0443 (7)
H18A0.13910.72700.57640.053*
H18B0.08670.77280.46210.053*
H18C0.10030.81530.59760.053*
H1N0.143 (3)0.7487 (15)0.463 (3)0.045 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0705 (14)0.0501 (12)0.0574 (12)0.0110 (10)0.0374 (11)0.0049 (9)
O20.0429 (10)0.0491 (11)0.0273 (9)0.0032 (8)0.0144 (7)0.0034 (7)
N10.0310 (10)0.0378 (11)0.0252 (10)0.0059 (8)0.0122 (8)0.0044 (8)
C10.0411 (14)0.0314 (13)0.0484 (15)0.0016 (11)0.0149 (12)0.0001 (11)
C20.0540 (16)0.0398 (15)0.0507 (17)0.0019 (13)0.0157 (14)0.0025 (12)
C30.0512 (16)0.0361 (15)0.065 (2)0.0022 (13)0.0063 (15)0.0054 (13)
C40.0422 (15)0.0315 (14)0.078 (2)0.0072 (12)0.0126 (15)0.0000 (13)
C50.0415 (15)0.0352 (14)0.0650 (19)0.0015 (11)0.0236 (14)0.0066 (12)
C60.0362 (13)0.0276 (12)0.0517 (15)0.0044 (10)0.0190 (12)0.0039 (10)
C70.0386 (13)0.0340 (13)0.0480 (15)0.0036 (11)0.0216 (12)0.0056 (11)
C80.0364 (12)0.0302 (12)0.0347 (12)0.0023 (10)0.0172 (10)0.0055 (9)
C90.0321 (12)0.0359 (13)0.0291 (12)0.0045 (10)0.0121 (10)0.0036 (9)
C100.0336 (12)0.0361 (13)0.0319 (12)0.0035 (10)0.0151 (10)0.0036 (10)
C110.0459 (14)0.0335 (13)0.0340 (13)0.0012 (11)0.0163 (11)0.0043 (10)
C120.0546 (16)0.0338 (14)0.0499 (16)0.0018 (12)0.0235 (14)0.0036 (11)
C130.0499 (16)0.0396 (15)0.0576 (17)0.0069 (12)0.0245 (14)0.0101 (13)
C140.0425 (15)0.0511 (17)0.0470 (16)0.0064 (13)0.0132 (12)0.0118 (13)
C150.0383 (13)0.0471 (15)0.0357 (13)0.0031 (11)0.0131 (11)0.0022 (11)
C160.0406 (14)0.0395 (14)0.0545 (17)0.0083 (12)0.0190 (13)0.0072 (12)
C170.0347 (12)0.0273 (11)0.0312 (12)0.0021 (9)0.0129 (10)0.0013 (9)
C180.0363 (13)0.0554 (17)0.0446 (15)0.0087 (12)0.0172 (12)0.0066 (12)
Geometric parameters (Å, º) top
O1—C71.227 (3)C9—C101.522 (3)
O2—C171.245 (3)C9—H91.0000
N1—C171.336 (3)C10—C111.393 (3)
N1—C91.473 (3)C10—C151.394 (3)
N1—H1N0.94 (3)C11—C121.396 (4)
C1—C61.390 (3)C11—H110.9500
C1—C21.392 (4)C12—C131.385 (4)
C1—H10.9500C12—H120.9500
C2—C31.386 (4)C13—C141.380 (4)
C2—H20.9500C13—H130.9500
C3—C41.381 (4)C14—C151.396 (4)
C3—H30.9500C14—H140.9500
C4—C51.380 (4)C15—H150.9500
C4—H40.9500C16—H16A0.9800
C5—C61.407 (3)C16—H16B0.9800
C5—H50.9500C16—H16C0.9800
C6—C71.494 (4)C17—C181.505 (3)
C7—C81.531 (3)C18—H18A0.9800
C8—C161.538 (3)C18—H18B0.9800
C8—C91.538 (3)C18—H18C0.9800
C8—H81.0000
C17—N1—C9123.2 (2)C8—C9—H9108.2
C17—N1—H1N117.8 (16)C11—C10—C15118.4 (2)
C9—N1—H1N119.0 (16)C11—C10—C9120.5 (2)
C6—C1—C2120.8 (3)C15—C10—C9121.0 (2)
C6—C1—H1119.6C10—C11—C12120.6 (2)
C2—C1—H1119.6C10—C11—H11119.7
C3—C2—C1119.6 (3)C12—C11—H11119.7
C3—C2—H2120.2C13—C12—C11120.2 (3)
C1—C2—H2120.2C13—C12—H12119.9
C4—C3—C2120.6 (3)C11—C12—H12119.9
C4—C3—H3119.7C14—C13—C12119.7 (3)
C2—C3—H3119.7C14—C13—H13120.2
C5—C4—C3119.6 (3)C12—C13—H13120.2
C5—C4—H4120.2C13—C14—C15120.2 (3)
C3—C4—H4120.2C13—C14—H14119.9
C4—C5—C6121.1 (3)C15—C14—H14119.9
C4—C5—H5119.4C10—C15—C14120.8 (3)
C6—C5—H5119.4C10—C15—H15119.6
C1—C6—C5118.2 (2)C14—C15—H15119.6
C1—C6—C7123.0 (2)C8—C16—H16A109.5
C5—C6—C7118.9 (2)C8—C16—H16B109.5
O1—C7—C6120.4 (2)H16A—C16—H16B109.5
O1—C7—C8119.9 (2)C8—C16—H16C109.5
C6—C7—C8119.6 (2)H16A—C16—H16C109.5
C7—C8—C16107.2 (2)H16B—C16—H16C109.5
C7—C8—C9110.49 (19)O2—C17—N1122.5 (2)
C16—C8—C9111.9 (2)O2—C17—C18121.0 (2)
C7—C8—H8109.1N1—C17—C18116.5 (2)
C16—C8—H8109.1C17—C18—H18A109.5
C9—C8—H8109.1C17—C18—H18B109.5
N1—C9—C10111.73 (19)H18A—C18—H18B109.5
N1—C9—C8108.67 (19)C17—C18—H18C109.5
C10—C9—C8111.73 (18)H18A—C18—H18C109.5
N1—C9—H9108.2H18B—C18—H18C109.5
C10—C9—H9108.2
C6—C1—C2—C30.8 (4)C7—C8—C9—N158.1 (2)
C1—C2—C3—C40.1 (4)C16—C8—C9—N1177.54 (19)
C2—C3—C4—C50.8 (4)C7—C8—C9—C10178.12 (19)
C3—C4—C5—C61.0 (4)C16—C8—C9—C1058.7 (3)
C2—C1—C6—C50.5 (4)N1—C9—C10—C1147.8 (3)
C2—C1—C6—C7178.6 (2)C8—C9—C10—C1174.1 (3)
C4—C5—C6—C10.4 (4)N1—C9—C10—C15133.1 (2)
C4—C5—C6—C7179.5 (2)C8—C9—C10—C15104.9 (2)
C1—C6—C7—O1174.8 (2)C15—C10—C11—C120.1 (3)
C5—C6—C7—O14.3 (4)C9—C10—C11—C12179.2 (2)
C1—C6—C7—C82.8 (3)C10—C11—C12—C131.1 (4)
C5—C6—C7—C8178.0 (2)C11—C12—C13—C141.3 (4)
O1—C7—C8—C1686.0 (3)C12—C13—C14—C150.3 (4)
C6—C7—C8—C1691.6 (3)C11—C10—C15—C141.0 (4)
O1—C7—C8—C936.1 (3)C9—C10—C15—C14179.9 (2)
C6—C7—C8—C9146.2 (2)C13—C14—C15—C100.9 (4)
C17—N1—C9—C10102.4 (2)C9—N1—C17—O23.4 (3)
C17—N1—C9—C8133.9 (2)C9—N1—C17—C18176.2 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C10–C15 and C1–C6 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.94 (3)1.98 (3)2.874 (3)158 (2)
C1—H1···Cg1i0.952.85 (1)3.649 (3)142 (1)
C16—H16A···Cg2ii0.982.98 (1)3.472 (3)112 (1)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y+3/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC18H19NO2
Mr281.34
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)9.156 (5), 17.668 (8), 10.103 (5)
β (°) 107.914 (7)
V3)1555.0 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.61 × 0.07 × 0.02
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2008)
Tmin, Tmax0.954, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
12600, 3028, 2386
Rint0.050
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.156, 1.00
No. of reflections3028
No. of parameters197
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.24

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C10–C15 and C1–C6 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.94 (3)1.98 (3)2.874 (3)158 (2)
C1—H1···Cg1i0.952.854 (3)3.649 (3)141.9 (3)
C16—H16A···Cg2ii0.982.978 (3)3.472 (3)112.4 (3)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y+3/2, z+3/2.
 

Acknowledgements

The authors thank Beijing Institute of Technology for the X-ray diffraction analysis.

References

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