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

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.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.070
• wR factor = 0.156
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     15.491
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.343
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7
PLAT918_ALERT_3_C Reflection(s) # with I(obs) much smaller I(calc)          1

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.61 mm
PLAT793_ALERT_4_G The Model has Chirality at C8      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C9      (Verify) ....          S
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......          !

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

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

Computing details

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

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	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

Crystal data

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) Å^3	Prism, colorless
Z = 4	0.61 × 0.07 × 0.02 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.070	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.156	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 1.630P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)

Special details

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 (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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···O2^i	0.94 (3)	1.98 (3)	2.874 (3)	158 (2)
C1—H1···Cg1^i	0.95	2.85 (1)	3.649 (3)	142 (1)
C16—H16A···Cg2^ii	0.98	2.98 (1)	3.472 (3)	112 (1)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y+3/2, −z+3/2.