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Journal logoIUCrDATA
ISSN: 2414-3146

2-(5-Methyl-1-benzo­furan-3-yl)-N-(2-phenyl­eth­yl)acetamide

aDepartment of Physics, Govt. First Grade College, Mulbagal, Kolar Dist 563 131, Karnataka, India, bDepartment of Physics, Govt. College for Women, Mandya 571 401, Karnataka, India, cDepartment of Physics, Govt. College for Women, Kolar 563 101, Karnataka, India, dDepartment of Chemistry, P.C. Jabin Science College, Hubli 580 031, Karnataka, India, eDepartment of Physics, Govt. First Grade College, Malur, Kolar 563 160, Karnataka, India, and fDepartment of Physics, Sapthagiri College of Engineering, Bangalore 560 057, Karnataka, India
*Correspondence e-mail: kvarjunagowda@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 31 January 2017; accepted 7 February 2017; online 10 February 2017)

The title compound, C19H19NO2, is non-planar with the phenyl ring of the phenethyl­acetamide residue inclined to the benzo­furan ring system by 84.8 (3)°. The methyl group lies in the plane of the fused ring system [C—C—C—C torsion angle = −179.6 (3)°]. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into chains along the a-axis direction. ππ stacking inter­actions with a centroid-to-centroid distances of 3.497 (3) Å further stabilize the structure, stacking the mol­ecules along a.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Benzo­furan derivatives with an amide linkage have attracted attention due to their wide range of biological activities. These include acting as melatonin receptor selective ligands (Wallez et al., 2002[Wallez, V., Durieux-Poissonnier, S., Chavatte, P., Boutin, J. A., Audinot, V., Nicolas, J. P., Bennejean, C., Delagrange, P., Renard, P. & Lesieur, D. (2002). J. Med. Chem. 45, 2788-2800.]), glycogen synthase kinase 3β inhibitors, which suppress proliferation and survival of pancreatic cancer cells (Gaisina et al., 2009[Gaisina, I. N., Gallier, F., Ougolkov, A. V., Kim, K. H., Kurome, T., Guo, S., Holzle, D., Luchini, D. N., Blond, S. Y., Billadeau, D. D. & Kozikowski, A. P. (2009). J. Med. Chem. 52, 1853-1863.]), and ischemic cell death inhibitors (Suh et al., 2010[Suh, J., Yi, K. Y., Lee, Y. S., Kim, E., Yum, E. K. & Yoo, S. (2010). Bioorg. Med. Chem. Lett. 20, 6362-6365.]). They are also used as anti­tubercular and anti­fungal (Telvekar et al., 2012[Telvekar, V. N., Belubbi, A., Bairwa, V. K. & Satardekar, K. (2012). Bioorg. Med. Chem. Lett. 22, 2343-2346.]) or anti­convulsant agents (Shakya et al., 2016[Shakya, A. K., Kamal, M., Balaramnavar, V. M., Bardaweel, S. K., Naik, R. R., Saxena, A. K. & Siddiqui, H. H. (2016). Acta Pharm. 66, 353-372.]). They inhibit mono­amine oxidase (Pisani et al., 2013[Pisani, L., Barletta, M., Soto-Otero, R., Nicolotti, O., Mendez-Alvarez, E., Catto, M., Introcaso, A., Stefanachi, A., Cellamare, S., Altomare, C. & Carotti, A. (2013). J. Med. Chem. 56, 2651-2664.]), the hepatitis C virus (Bowman et al., 2015[Bowman, R. K., Bullock, K. M., Copley, R. C. B., Deschamps, N. M., McClure, M. S., Powers, J. D., Wolters, A. M., Wu, L. & Xie, S. (2015). J. Org. Chem. 80, 9610-9619.]) and NF-kB activity (Choi et al., 2016[Choi, M., Jo, H., Kim, D., Yun, J., Kang, S. S., Kim, Y., Jung, K. K., Hong, J. T., Cho, J., Kwak, J. H. & Lee, H. (2016). Arch. Pharm. Res. 39, 618-630.]). Other pharmaceutical applications include the treatment of cognitive disorders (Mazurov et al., 2012[Mazurov, A. A., Kombo, D. C., Hauser, T. A., Miao, L., Dull, G., Genus, J. F., Fedorov, N. B., Benson, L., Sidach, S., Xiao, Y., Hammond, P. S., James, J. W., Miller, C. H. & Yohannes, D. (2012). J. Med. Chem. 55, 9793-9809.]) and as anti-oestrogen breast cancer agents (Li et al., 2013[Li, X. Y., He, B. F., Luo, H. J., Huang, N. Y. & Deng, W. Q. (2013). Bioorg. Med. Chem. Lett. 23, 4617-4621.]). Chemically they are used as inter­mediates for the synthesis of morphine alkaloids (France et al., 2008[France, S., Boonsombat, J., Leverett, C. A. & Padwa, A. (2008). J. Org. Chem. 73, 8120-8123.]).

The title compound (Fig. 1[link]) is non-planar. The C14–C18 phenyl ring of the phenethyl­acetamide residue is inclined to the planar benzo­furan ring system by 84.8 (3)°. The r.m.s. deviation from the plane through the ten atoms of the benzo­furan ring system is 0.011 Å. The mol­ecular structure is similar to that observed for 2-(5-methyl-1-benzo­furan-3-yl)acetic acid (Ramprasad et al., 2016[Ramprasad, N., Gowda, R., Gowda, K. V. A. & Basanagouda, M. (2016). IUCrData, 1, x160170.]).

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom numbering.

In the crystal, N1—H1⋯O2 hydrogen bonds (Table 1[link]) link the mol­ecules into chains along the a-axis direction. A ππ stacking inter­action [CgCgii = 3.497 (3) Å, Cg is the centroid of the O1/C5/C6/C8/C9 ring; symmetry code: (ii) 2 − x, −y, 2 − z] further stabilizes the structure, Fig. 2[link], stacking the mol­ecules along a.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.79 (3) 2.06 (3) 2.849 (3) 173 (3)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z].
[Figure 2]
Figure 2
Packing diagram viewed along the b axis, with hydrogen bonds drawn as dashed lines. Ring centroids are shown as coloured spheres and ππ contacts as dotted lines.

Synthesis and crystallization

5-Methyl-benzo­furan-3-acetic acid (10 mmol) (Basanagouda et al., 2015[Basanagouda, M., Narayanachar, , Majati, I. B., Mulimani, S. S., Sunnal, S. B., Nadiger, R. V., Ghanti, A. S., Gudageri, S. F., Naik, R. & Nayak, A. (2015). Synth. Commun. 45, 2195-2202.]; Uriarte et al., 1995[Uriarte, E., Fall, Y., Santana, L. & Teijeira, M. (1995). Heterocycles, 41, 647-648.]) was refluxed with phenyl­ethyl­amine (10 mmol) in benzene (30 ml) for 7 h (monitored by TLC). The solvent was removed to obtain a colourless solid, which was crystallized from a mixture of benzene and petroleum ether (1:1). Crystals suitable for diffraction studies were obtained by the slow evaporation of a solvent mixture of benzene and petroleum ether (1:1).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C19H19NO2
Mr 293.35
Crystal system, space group Monoclinic, P21/a
Temperature (K) 293
a, b, c (Å) 9.440 (6), 14.6051 (15), 12.321 (2)
β (°) 105.68 (3)
V3) 1635.5 (10)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.61
Crystal size (mm) 0.30 × 0.20 × 0.20
 
Data collection
Diffractometer Enraf–Nonius CAD-4
Absorption correction ψ scan (CAD-4 Software; Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.])
Tmin, Tmax 0.884, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections 2962, 2777, 1611
Rint 0.019
(sin θ/λ)max−1) 0.588
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.169, 1.04
No. of reflections 2777
No. of parameters 205
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.22, −0.20
Computer programs: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]), XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data


Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

2-(5-Methyl-1-benzofuran-3-yl)-N-(2-phenylethyl)acetamide top
Crystal data top
C19H19NO2F(000) = 624
Mr = 293.35Dx = 1.191 Mg m3
Monoclinic, P21/aMelting point: 374 K
Hall symbol: -P 2yabCu Kα radiation, λ = 1.54180 Å
a = 9.440 (6) ÅCell parameters from 25 reflections
b = 14.6051 (15) Åθ = 20–30°
c = 12.321 (2) ŵ = 0.61 mm1
β = 105.68 (3)°T = 293 K
V = 1635.5 (10) Å3Block, colourless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1611 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 65.0°, θmin = 3.7°
ω–2τ scanh = 011
Absorption correction: ψ scan
(CAD-4 Software; Enraf–Nonius, 1989)
k = 017
Tmin = 0.884, Tmax = 0.983l = 1413
2962 measured reflections2 standard reflections every 3600 min
2777 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0836P)2 + 0.197P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2777 reflectionsΔρmax = 0.22 e Å3
205 parametersΔρmin = 0.20 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: 0.0138 (11)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C11.4210 (5)0.2541 (3)1.2438 (3)0.1106 (13)
H1A1.43620.23081.31890.166*
H1B1.35440.30511.23280.166*
H1C1.51340.27371.23310.166*
C21.3564 (4)0.1798 (2)1.1596 (3)0.0759 (9)
C31.4336 (4)0.0988 (3)1.1569 (3)0.0846 (11)
H31.52530.09141.20820.101*
C41.3806 (4)0.0296 (3)1.0820 (3)0.0785 (10)
H41.43360.02411.08170.094*
C51.2452 (3)0.0433 (2)1.0074 (3)0.0628 (8)
C61.1619 (3)0.12179 (19)1.0061 (2)0.0563 (8)
C71.2192 (3)0.1905 (2)1.0831 (3)0.0671 (8)
H71.16560.24381.08360.081*
C81.0405 (3)0.0264 (2)0.8746 (3)0.0699 (9)
H80.96790.00070.81600.084*
C91.0287 (3)0.10883 (19)0.9184 (2)0.0582 (8)
C100.8999 (3)0.1722 (2)0.8871 (3)0.0641 (8)
H10A0.87610.19160.95530.077*
H10B0.81590.13880.84160.077*
C110.9241 (3)0.25580 (18)0.8229 (2)0.0516 (7)
C120.8114 (3)0.39129 (18)0.7207 (3)0.0611 (8)
H12A0.90750.39640.70690.073*
H12B0.79810.44440.76430.073*
C130.6974 (4)0.3930 (2)0.6110 (3)0.0842 (10)
H13A0.60120.39940.62410.101*
H13B0.69920.33540.57210.101*
C140.7222 (4)0.4706 (2)0.5379 (3)0.0712 (9)
C150.6933 (5)0.5581 (3)0.5605 (3)0.0926 (11)
H150.65020.57000.61860.111*
C160.7264 (5)0.6302 (3)0.4992 (4)0.1059 (13)
H160.70480.68980.51630.127*
C170.7900 (5)0.6152 (3)0.4146 (4)0.1068 (14)
H170.81480.66400.37470.128*
C180.8165 (6)0.5295 (4)0.3895 (4)0.1203 (15)
H180.85750.51840.33000.144*
C190.7842 (5)0.4564 (3)0.4501 (4)0.1108 (14)
H190.80470.39710.43150.133*
N10.8092 (2)0.31022 (16)0.7869 (2)0.0546 (7)
O11.1717 (2)0.01657 (14)0.92533 (19)0.0737 (6)
O21.04377 (19)0.27316 (14)0.8051 (2)0.0804 (7)
H10.736 (4)0.290 (2)0.797 (3)0.077 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.105 (3)0.123 (3)0.099 (3)0.008 (3)0.019 (2)0.014 (3)
C20.072 (2)0.085 (2)0.075 (2)0.0026 (19)0.0275 (18)0.0129 (19)
C30.063 (2)0.104 (3)0.085 (3)0.018 (2)0.0183 (19)0.024 (2)
C40.068 (2)0.084 (2)0.089 (2)0.0300 (19)0.0306 (19)0.025 (2)
C50.0632 (19)0.0623 (18)0.071 (2)0.0153 (15)0.0329 (16)0.0176 (16)
C60.0538 (17)0.0561 (17)0.0680 (19)0.0106 (14)0.0321 (15)0.0174 (15)
C70.0630 (19)0.0658 (19)0.081 (2)0.0104 (16)0.0336 (17)0.0132 (18)
C80.066 (2)0.067 (2)0.079 (2)0.0054 (16)0.0227 (17)0.0184 (17)
C90.0550 (17)0.0561 (18)0.071 (2)0.0068 (14)0.0301 (16)0.0203 (15)
C100.0429 (15)0.0698 (19)0.085 (2)0.0051 (13)0.0267 (15)0.0200 (16)
C110.0365 (13)0.0570 (16)0.0650 (17)0.0033 (12)0.0200 (12)0.0083 (14)
C120.0465 (16)0.0534 (16)0.082 (2)0.0024 (13)0.0152 (15)0.0128 (15)
C130.092 (2)0.075 (2)0.075 (2)0.016 (2)0.0035 (19)0.0106 (18)
C140.080 (2)0.059 (2)0.068 (2)0.0005 (17)0.0083 (17)0.0073 (17)
C150.117 (3)0.073 (2)0.090 (3)0.010 (2)0.032 (2)0.013 (2)
C160.140 (4)0.068 (3)0.107 (3)0.013 (2)0.027 (3)0.016 (2)
C170.133 (4)0.089 (3)0.092 (3)0.004 (3)0.018 (3)0.034 (2)
C180.153 (4)0.126 (4)0.097 (3)0.015 (3)0.060 (3)0.023 (3)
C190.159 (4)0.084 (3)0.096 (3)0.026 (3)0.045 (3)0.012 (2)
N10.0339 (12)0.0570 (14)0.0766 (17)0.0029 (11)0.0212 (11)0.0144 (12)
O10.0800 (15)0.0640 (13)0.0849 (15)0.0187 (12)0.0356 (12)0.0125 (12)
O20.0422 (11)0.0794 (14)0.1325 (19)0.0128 (10)0.0457 (12)0.0399 (13)
Geometric parameters (Å, º) top
C1—C21.511 (5)C11—O21.234 (3)
C1—H1A0.9600C11—N11.321 (3)
C1—H1B0.9600C12—N11.441 (3)
C1—H1C0.9600C12—C131.483 (4)
C2—C71.389 (4)C12—H12A0.9700
C2—C31.396 (5)C12—H12B0.9700
C3—C41.369 (5)C13—C141.504 (4)
C3—H30.9300C13—H13A0.9700
C4—C51.372 (4)C13—H13B0.9700
C4—H40.9300C14—C151.352 (5)
C5—O11.375 (4)C14—C191.377 (5)
C5—C61.387 (4)C15—C161.380 (5)
C6—C71.386 (4)C15—H150.9300
C6—C91.432 (4)C16—C171.355 (6)
C7—H70.9300C16—H160.9300
C8—C91.337 (4)C17—C181.329 (6)
C8—O11.378 (3)C17—H170.9300
C8—H80.9300C18—C191.383 (6)
C9—C101.493 (4)C18—H180.9300
C10—C111.505 (4)C19—H190.9300
C10—H10A0.9700N1—H10.79 (3)
C10—H10B0.9700
C2—C1—H1A109.5O2—C11—C10122.4 (2)
C2—C1—H1B109.5N1—C11—C10115.9 (2)
H1A—C1—H1B109.5N1—C12—C13114.3 (2)
C2—C1—H1C109.5N1—C12—H12A108.7
H1A—C1—H1C109.5C13—C12—H12A108.7
H1B—C1—H1C109.5N1—C12—H12B108.7
C7—C2—C3118.4 (4)C13—C12—H12B108.7
C7—C2—C1121.0 (3)H12A—C12—H12B107.6
C3—C2—C1120.6 (3)C12—C13—C14111.5 (3)
C4—C3—C2123.0 (3)C12—C13—H13A109.3
C4—C3—H3118.5C14—C13—H13A109.3
C2—C3—H3118.5C12—C13—H13B109.3
C3—C4—C5116.6 (3)C14—C13—H13B109.3
C3—C4—H4121.7H13A—C13—H13B108.0
C5—C4—H4121.7C15—C14—C19117.1 (3)
C4—C5—O1126.3 (3)C15—C14—C13121.1 (3)
C4—C5—C6123.5 (3)C19—C14—C13121.6 (3)
O1—C5—C6110.2 (3)C14—C15—C16121.4 (4)
C7—C6—C5118.3 (3)C14—C15—H15119.3
C7—C6—C9135.4 (3)C16—C15—H15119.3
C5—C6—C9106.2 (3)C17—C16—C15120.7 (4)
C6—C7—C2120.2 (3)C17—C16—H16119.7
C6—C7—H7119.9C15—C16—H16119.7
C2—C7—H7119.9C18—C17—C16118.8 (4)
C9—C8—O1112.9 (3)C18—C17—H17120.6
C9—C8—H8123.5C16—C17—H17120.6
O1—C8—H8123.5C17—C18—C19121.2 (4)
C8—C9—C6105.8 (3)C17—C18—H18119.4
C8—C9—C10127.2 (3)C19—C18—H18119.4
C6—C9—C10127.0 (3)C14—C19—C18120.7 (4)
C9—C10—C11114.2 (2)C14—C19—H19119.6
C9—C10—H10A108.7C18—C19—H19119.6
C11—C10—H10A108.7C11—N1—C12123.3 (2)
C9—C10—H10B108.7C11—N1—H1113 (2)
C11—C10—H10B108.7C12—N1—H1123 (2)
H10A—C10—H10B107.6C5—O1—C8104.9 (2)
O2—C11—N1121.6 (3)
C7—C2—C3—C40.2 (5)C6—C9—C10—C1175.3 (4)
C1—C2—C3—C4179.6 (3)C9—C10—C11—O24.8 (4)
C2—C3—C4—C50.3 (5)C9—C10—C11—N1175.4 (3)
C3—C4—C5—O1179.8 (3)N1—C12—C13—C14170.0 (3)
C3—C4—C5—C60.8 (5)C12—C13—C14—C1573.6 (4)
C4—C5—C6—C70.9 (4)C12—C13—C14—C19101.9 (4)
O1—C5—C6—C7179.7 (2)C19—C14—C15—C160.9 (6)
C4—C5—C6—C9178.9 (3)C13—C14—C15—C16174.9 (3)
O1—C5—C6—C90.5 (3)C14—C15—C16—C170.4 (7)
C5—C6—C7—C20.3 (4)C15—C16—C17—C181.8 (7)
C9—C6—C7—C2179.4 (3)C16—C17—C18—C191.9 (8)
C3—C2—C7—C60.2 (4)C15—C14—C19—C180.7 (6)
C1—C2—C7—C6179.6 (3)C13—C14—C19—C18175.0 (4)
O1—C8—C9—C60.5 (3)C17—C18—C19—C140.7 (8)
O1—C8—C9—C10177.4 (2)O2—C11—N1—C122.5 (4)
C7—C6—C9—C8179.8 (3)C10—C11—N1—C12177.7 (3)
C5—C6—C9—C80.0 (3)C13—C12—N1—C11123.3 (3)
C7—C6—C9—C102.8 (5)C4—C5—O1—C8178.6 (3)
C5—C6—C9—C10176.9 (3)C6—C5—O1—C80.8 (3)
C8—C9—C10—C11108.4 (3)C9—C8—O1—C50.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.79 (3)2.06 (3)2.849 (3)173 (3)
Symmetry code: (i) x1/2, y+1/2, z.
 

Acknowledgements

The authors thank the SAIF IIT Madras, Chennai, India, for the data collection.

References

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