N-(2-Methyl-3-oxo-1,3-diphenyl-prop-yl)acetamide.

In the title compound, C18H19NO2, the dihedral angle between the benzene rings is 42.0 (1)°. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯π inter-actions.

Related literature

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

Crystal data

C18H19NO2

M = 281.34

Monoclinic,

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 ▶) T min = 0.954, T max = 0.998

12600 measured reflections

3028 independent reflections

2386 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 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

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007320/lx2279sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007320/lx2279Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007320/lx2279Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H19NO2	F(000) = 600
Mr = 281.34	Dx = 1.202 Mg m−3
Monoclinic, P21/c	Melting point = 439–441 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.156 (5) Å	Cell parameters from 3372 reflections
b = 17.668 (8) Å	θ = 2.3–29.0°
c = 10.103 (5) Å	µ = 0.08 mm−1
β = 107.914 (7)°	T = 153 K
V = 1555.0 (13) Å3	Prism, colorless
Z = 4	0.61 × 0.07 × 0.02 mm

Rigaku AFC10/Saturn724+ diffractometer	3028 independent reflections
Radiation source: Rotating Anode	2386 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 28.5714 pixels mm-1	θmax = 26.0°, θmin = 2.3°
phi and ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −20→21
Tmin = 0.954, Tmax = 0.998	l = −12→12
12600 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070	H 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 reflections	Δρmax = 0.22 e Å−3
197 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)

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.

	x	y	z	Uiso*/Ueq
O1	0.2368 (2)	0.56897 (11)	0.6152 (2)	0.0553 (6)
O2	0.13769 (19)	0.74116 (10)	0.76594 (17)	0.0390 (4)
N1	0.1849 (2)	0.74059 (11)	0.5589 (2)	0.0305 (5)
C1	0.2662 (3)	0.55877 (14)	0.2653 (3)	0.0401 (6)
H1	0.3342	0.5998	0.2680	0.048*
C2	0.2150 (3)	0.51473 (15)	0.1457 (3)	0.0483 (7)
H2	0.2490	0.5252	0.0677	0.058*
C3	0.1143 (3)	0.45551 (16)	0.1410 (3)	0.0535 (8)
H3	0.0791	0.4255	0.0593	0.064*
C4	0.0646 (3)	0.43978 (15)	0.2540 (3)	0.0520 (8)
H4	−0.0055	0.3995	0.2497	0.062*
C5	0.1172 (3)	0.48288 (15)	0.3731 (3)	0.0456 (7)
H5	0.0841	0.4714	0.4512	0.055*
C6	0.2190 (3)	0.54355 (13)	0.3808 (3)	0.0373 (6)
C7	0.2732 (3)	0.58798 (14)	0.5128 (3)	0.0384 (6)
C8	0.3799 (3)	0.65579 (13)	0.5217 (2)	0.0324 (5)
H8	0.3626	0.6769	0.4263	0.039*
C9	0.3469 (3)	0.71774 (13)	0.6157 (2)	0.0317 (5)
H9	0.3627	0.6956	0.7101	0.038*
C10	0.4548 (3)	0.78490 (13)	0.6304 (2)	0.0327 (5)
C11	0.4362 (3)	0.83580 (13)	0.5211 (3)	0.0369 (6)
H11	0.3546	0.8289	0.4372	0.044*
C12	0.5363 (3)	0.89691 (15)	0.5338 (3)	0.0444 (7)
H12	0.5236	0.9308	0.4580	0.053*
C13	0.6541 (3)	0.90834 (16)	0.6565 (3)	0.0472 (7)
H13	0.7209	0.9505	0.6656	0.057*
C14	0.6741 (3)	0.85819 (16)	0.7654 (3)	0.0470 (7)
H14	0.7551	0.8657	0.8495	0.056*
C15	0.5756 (3)	0.79640 (15)	0.7523 (3)	0.0400 (6)
H15	0.5910	0.7618	0.8273	0.048*
C16	0.5456 (3)	0.62634 (15)	0.5778 (3)	0.0439 (6)
H16A	0.5626	0.6044	0.6704	0.053*
H16B	0.6174	0.6683	0.5838	0.053*
H16C	0.5626	0.5875	0.5148	0.053*
C17	0.0921 (3)	0.74884 (12)	0.6372 (2)	0.0304 (5)
C18	−0.0729 (3)	0.76761 (16)	0.5617 (3)	0.0443 (7)
H18A	−0.1391	0.7270	0.5764	0.053*
H18B	−0.0867	0.7728	0.4621	0.053*
H18C	−0.1003	0.8153	0.5976	0.053*
H1N	0.143 (3)	0.7487 (15)	0.463 (3)	0.045 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0705 (14)	0.0501 (12)	0.0574 (12)	−0.0110 (10)	0.0374 (11)	0.0049 (9)
O2	0.0429 (10)	0.0491 (11)	0.0273 (9)	−0.0032 (8)	0.0144 (7)	−0.0034 (7)
N1	0.0310 (10)	0.0378 (11)	0.0252 (10)	0.0059 (8)	0.0122 (8)	0.0044 (8)
C1	0.0411 (14)	0.0314 (13)	0.0484 (15)	−0.0016 (11)	0.0149 (12)	−0.0001 (11)
C2	0.0540 (16)	0.0398 (15)	0.0507 (17)	0.0019 (13)	0.0157 (14)	−0.0025 (12)
C3	0.0512 (16)	0.0361 (15)	0.065 (2)	−0.0022 (13)	0.0063 (15)	−0.0054 (13)
C4	0.0422 (15)	0.0315 (14)	0.078 (2)	−0.0072 (12)	0.0126 (15)	0.0000 (13)
C5	0.0415 (15)	0.0352 (14)	0.0650 (19)	0.0015 (11)	0.0236 (14)	0.0066 (12)
C6	0.0362 (13)	0.0276 (12)	0.0517 (15)	0.0044 (10)	0.0190 (12)	0.0039 (10)
C7	0.0386 (13)	0.0340 (13)	0.0480 (15)	0.0036 (11)	0.0216 (12)	0.0056 (11)
C8	0.0364 (12)	0.0302 (12)	0.0347 (12)	0.0023 (10)	0.0172 (10)	0.0055 (9)
C9	0.0321 (12)	0.0359 (13)	0.0291 (12)	0.0045 (10)	0.0121 (10)	0.0036 (9)
C10	0.0336 (12)	0.0361 (13)	0.0319 (12)	0.0035 (10)	0.0151 (10)	−0.0036 (10)
C11	0.0459 (14)	0.0335 (13)	0.0340 (13)	−0.0012 (11)	0.0163 (11)	−0.0043 (10)
C12	0.0546 (16)	0.0338 (14)	0.0499 (16)	−0.0018 (12)	0.0235 (14)	−0.0036 (11)
C13	0.0499 (16)	0.0396 (15)	0.0576 (17)	−0.0069 (12)	0.0245 (14)	−0.0101 (13)
C14	0.0425 (15)	0.0511 (17)	0.0470 (16)	−0.0064 (13)	0.0132 (12)	−0.0118 (13)
C15	0.0383 (13)	0.0471 (15)	0.0357 (13)	0.0031 (11)	0.0131 (11)	−0.0022 (11)
C16	0.0406 (14)	0.0395 (14)	0.0545 (17)	0.0083 (12)	0.0190 (13)	0.0072 (12)
C17	0.0347 (12)	0.0273 (11)	0.0312 (12)	−0.0021 (9)	0.0129 (10)	−0.0013 (9)
C18	0.0363 (13)	0.0554 (17)	0.0446 (15)	0.0087 (12)	0.0172 (12)	0.0066 (12)

O1—C7	1.227 (3)	C9—C10	1.522 (3)
O2—C17	1.245 (3)	C9—H9	1.0000
N1—C17	1.336 (3)	C10—C11	1.393 (3)
N1—C9	1.473 (3)	C10—C15	1.394 (3)
N1—H1N	0.94 (3)	C11—C12	1.396 (4)
C1—C6	1.390 (3)	C11—H11	0.9500
C1—C2	1.392 (4)	C12—C13	1.385 (4)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.386 (4)	C13—C14	1.380 (4)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.381 (4)	C14—C15	1.396 (4)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.380 (4)	C15—H15	0.9500
C4—H4	0.9500	C16—H16A	0.9800
C5—C6	1.407 (3)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—C7	1.494 (4)	C17—C18	1.505 (3)
C7—C8	1.531 (3)	C18—H18A	0.9800
C8—C16	1.538 (3)	C18—H18B	0.9800
C8—C9	1.538 (3)	C18—H18C	0.9800
C8—H8	1.0000
C17—N1—C9	123.2 (2)	C8—C9—H9	108.2
C17—N1—H1N	117.8 (16)	C11—C10—C15	118.4 (2)
C9—N1—H1N	119.0 (16)	C11—C10—C9	120.5 (2)
C6—C1—C2	120.8 (3)	C15—C10—C9	121.0 (2)
C6—C1—H1	119.6	C10—C11—C12	120.6 (2)
C2—C1—H1	119.6	C10—C11—H11	119.7
C3—C2—C1	119.6 (3)	C12—C11—H11	119.7
C3—C2—H2	120.2	C13—C12—C11	120.2 (3)
C1—C2—H2	120.2	C13—C12—H12	119.9
C4—C3—C2	120.6 (3)	C11—C12—H12	119.9
C4—C3—H3	119.7	C14—C13—C12	119.7 (3)
C2—C3—H3	119.7	C14—C13—H13	120.2
C5—C4—C3	119.6 (3)	C12—C13—H13	120.2
C5—C4—H4	120.2	C13—C14—C15	120.2 (3)
C3—C4—H4	120.2	C13—C14—H14	119.9
C4—C5—C6	121.1 (3)	C15—C14—H14	119.9
C4—C5—H5	119.4	C10—C15—C14	120.8 (3)
C6—C5—H5	119.4	C10—C15—H15	119.6
C1—C6—C5	118.2 (2)	C14—C15—H15	119.6
C1—C6—C7	123.0 (2)	C8—C16—H16A	109.5
C5—C6—C7	118.9 (2)	C8—C16—H16B	109.5
O1—C7—C6	120.4 (2)	H16A—C16—H16B	109.5
O1—C7—C8	119.9 (2)	C8—C16—H16C	109.5
C6—C7—C8	119.6 (2)	H16A—C16—H16C	109.5
C7—C8—C16	107.2 (2)	H16B—C16—H16C	109.5
C7—C8—C9	110.49 (19)	O2—C17—N1	122.5 (2)
C16—C8—C9	111.9 (2)	O2—C17—C18	121.0 (2)
C7—C8—H8	109.1	N1—C17—C18	116.5 (2)
C16—C8—H8	109.1	C17—C18—H18A	109.5
C9—C8—H8	109.1	C17—C18—H18B	109.5
N1—C9—C10	111.73 (19)	H18A—C18—H18B	109.5
N1—C9—C8	108.67 (19)	C17—C18—H18C	109.5
C10—C9—C8	111.73 (18)	H18A—C18—H18C	109.5
N1—C9—H9	108.2	H18B—C18—H18C	109.5
C10—C9—H9	108.2
C6—C1—C2—C3	0.8 (4)	C7—C8—C9—N1	−58.1 (2)
C1—C2—C3—C4	−0.1 (4)	C16—C8—C9—N1	−177.54 (19)
C2—C3—C4—C5	−0.8 (4)	C7—C8—C9—C10	178.12 (19)
C3—C4—C5—C6	1.0 (4)	C16—C8—C9—C10	58.7 (3)
C2—C1—C6—C5	−0.5 (4)	N1—C9—C10—C11	−47.8 (3)
C2—C1—C6—C7	178.6 (2)	C8—C9—C10—C11	74.1 (3)
C4—C5—C6—C1	−0.4 (4)	N1—C9—C10—C15	133.1 (2)
C4—C5—C6—C7	−179.5 (2)	C8—C9—C10—C15	−104.9 (2)
C1—C6—C7—O1	−174.8 (2)	C15—C10—C11—C12	−0.1 (3)
C5—C6—C7—O1	4.3 (4)	C9—C10—C11—C12	−179.2 (2)
C1—C6—C7—C8	2.8 (3)	C10—C11—C12—C13	−1.1 (4)
C5—C6—C7—C8	−178.0 (2)	C11—C12—C13—C14	1.3 (4)
O1—C7—C8—C16	86.0 (3)	C12—C13—C14—C15	−0.3 (4)
C6—C7—C8—C16	−91.6 (3)	C11—C10—C15—C14	1.0 (4)
O1—C7—C8—C9	−36.1 (3)	C9—C10—C15—C14	−179.9 (2)
C6—C7—C8—C9	146.2 (2)	C13—C14—C15—C10	−0.9 (4)
C17—N1—C9—C10	−102.4 (2)	C9—N1—C17—O2	3.4 (3)
C17—N1—C9—C8	133.9 (2)	C9—N1—C17—C18	−176.2 (2)

D—H···A	D—H	H···A	D···A	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—H16A···Cg2ii	0.98	2.98 (1)	3.472 (3)	112 (1)

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	D⋯A	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—H16A⋯Cg2ii	0.98	2.98 (1)	3.472 (3)	112 (1)

Symmetry codes: (i) ; (ii) .