organic compounds
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
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. π–π stacking interactions with a centroid-to-centroid distances of 3.497 (3) Å further stabilize the structure, stacking the molecules along a.
Keywords: crystal structure; benzofuran; hydrogen bonding; π–π stacking.
CCDC reference: 1503758
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), glycogen synthase kinase 3β inhibitors, which suppress proliferation and survival of pancreatic cancer cells (Gaisina et al., 2009), and ischemic cell death inhibitors (Suh et al., 2010). They are also used as antitubercular and antifungal (Telvekar et al., 2012) or anticonvulsant agents (Shakya et al., 2016). They inhibit monoamine oxidase (Pisani et al., 2013), the hepatitis C virus (Bowman et al., 2015) and NF-kB activity (Choi et al., 2016). Other pharmaceutical applications include the treatment of cognitive disorders (Mazurov et al., 2012) and as anti-oestrogen breast cancer agents (Li et al., 2013). Chemically they are used as intermediates for the synthesis of morphine (France et al., 2008).
The title compound (Fig. 1) 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).
In the crystal, N1—H1⋯O2 hydrogen bonds (Table 1) link the molecules into chains along the a-axis direction. A π–π stacking interaction [Cg⋯Cgii = 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, stacking the molecules along a.
Synthesis and crystallization
5-Methyl-benzofuran-3-acetic acid (10 mmol) (Basanagouda et al., 2015; Uriarte et al., 1995) 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 .
details are summarized in Table 2Structural data
CCDC reference: 1503758
https://doi.org/10.1107/S2414314617002000/sj4086sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002000/sj4086Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617002000/sj4086Isup3.cml
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
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).C19H19NO2 | F(000) = 624 |
Mr = 293.35 | Dx = 1.191 Mg m−3 |
Monoclinic, P21/a | Melting point: 374 K |
Hall symbol: -P 2yab | Cu Kα radiation, λ = 1.54180 Å |
a = 9.440 (6) Å | Cell parameters from 25 reflections |
b = 14.6051 (15) Å | θ = 20–30° |
c = 12.321 (2) Å | µ = 0.61 mm−1 |
β = 105.68 (3)° | T = 293 K |
V = 1635.5 (10) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 1611 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 65.0°, θmin = 3.7° |
ω–2τ scan | h = 0→11 |
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989) | k = 0→17 |
Tmin = 0.884, Tmax = 0.983 | l = −14→13 |
2962 measured reflections | 2 standard reflections every 3600 min |
2777 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H 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 reflections | Δρmax = 0.22 e Å−3 |
205 parameters | Δρmin = −0.20 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: 0.0138 (11) |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.4210 (5) | 0.2541 (3) | 1.2438 (3) | 0.1106 (13) | |
H1A | 1.4362 | 0.2308 | 1.3189 | 0.166* | |
H1B | 1.3544 | 0.3051 | 1.2328 | 0.166* | |
H1C | 1.5134 | 0.2737 | 1.2331 | 0.166* | |
C2 | 1.3564 (4) | 0.1798 (2) | 1.1596 (3) | 0.0759 (9) | |
C3 | 1.4336 (4) | 0.0988 (3) | 1.1569 (3) | 0.0846 (11) | |
H3 | 1.5253 | 0.0914 | 1.2082 | 0.101* | |
C4 | 1.3806 (4) | 0.0296 (3) | 1.0820 (3) | 0.0785 (10) | |
H4 | 1.4336 | −0.0241 | 1.0817 | 0.094* | |
C5 | 1.2452 (3) | 0.0433 (2) | 1.0074 (3) | 0.0628 (8) | |
C6 | 1.1619 (3) | 0.12179 (19) | 1.0061 (2) | 0.0563 (8) | |
C7 | 1.2192 (3) | 0.1905 (2) | 1.0831 (3) | 0.0671 (8) | |
H7 | 1.1656 | 0.2438 | 1.0836 | 0.081* | |
C8 | 1.0405 (3) | 0.0264 (2) | 0.8746 (3) | 0.0699 (9) | |
H8 | 0.9679 | 0.0007 | 0.8160 | 0.084* | |
C9 | 1.0287 (3) | 0.10883 (19) | 0.9184 (2) | 0.0582 (8) | |
C10 | 0.8999 (3) | 0.1722 (2) | 0.8871 (3) | 0.0641 (8) | |
H10A | 0.8761 | 0.1916 | 0.9553 | 0.077* | |
H10B | 0.8159 | 0.1388 | 0.8416 | 0.077* | |
C11 | 0.9241 (3) | 0.25580 (18) | 0.8229 (2) | 0.0516 (7) | |
C12 | 0.8114 (3) | 0.39129 (18) | 0.7207 (3) | 0.0611 (8) | |
H12A | 0.9075 | 0.3964 | 0.7069 | 0.073* | |
H12B | 0.7981 | 0.4444 | 0.7643 | 0.073* | |
C13 | 0.6974 (4) | 0.3930 (2) | 0.6110 (3) | 0.0842 (10) | |
H13A | 0.6012 | 0.3994 | 0.6241 | 0.101* | |
H13B | 0.6992 | 0.3354 | 0.5721 | 0.101* | |
C14 | 0.7222 (4) | 0.4706 (2) | 0.5379 (3) | 0.0712 (9) | |
C15 | 0.6933 (5) | 0.5581 (3) | 0.5605 (3) | 0.0926 (11) | |
H15 | 0.6502 | 0.5700 | 0.6186 | 0.111* | |
C16 | 0.7264 (5) | 0.6302 (3) | 0.4992 (4) | 0.1059 (13) | |
H16 | 0.7048 | 0.6898 | 0.5163 | 0.127* | |
C17 | 0.7900 (5) | 0.6152 (3) | 0.4146 (4) | 0.1068 (14) | |
H17 | 0.8148 | 0.6640 | 0.3747 | 0.128* | |
C18 | 0.8165 (6) | 0.5295 (4) | 0.3895 (4) | 0.1203 (15) | |
H18 | 0.8575 | 0.5184 | 0.3300 | 0.144* | |
C19 | 0.7842 (5) | 0.4564 (3) | 0.4501 (4) | 0.1108 (14) | |
H19 | 0.8047 | 0.3971 | 0.4315 | 0.133* | |
N1 | 0.8092 (2) | 0.31022 (16) | 0.7869 (2) | 0.0546 (7) | |
O1 | 1.1717 (2) | −0.01657 (14) | 0.92533 (19) | 0.0737 (6) | |
O2 | 1.04377 (19) | 0.27316 (14) | 0.8051 (2) | 0.0804 (7) | |
H1 | 0.736 (4) | 0.290 (2) | 0.797 (3) | 0.077 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.105 (3) | 0.123 (3) | 0.099 (3) | −0.008 (3) | 0.019 (2) | −0.014 (3) |
C2 | 0.072 (2) | 0.085 (2) | 0.075 (2) | 0.0026 (19) | 0.0275 (18) | 0.0129 (19) |
C3 | 0.063 (2) | 0.104 (3) | 0.085 (3) | 0.018 (2) | 0.0183 (19) | 0.024 (2) |
C4 | 0.068 (2) | 0.084 (2) | 0.089 (2) | 0.0300 (19) | 0.0306 (19) | 0.025 (2) |
C5 | 0.0632 (19) | 0.0623 (18) | 0.071 (2) | 0.0153 (15) | 0.0329 (16) | 0.0176 (16) |
C6 | 0.0538 (17) | 0.0561 (17) | 0.0680 (19) | 0.0106 (14) | 0.0321 (15) | 0.0174 (15) |
C7 | 0.0630 (19) | 0.0658 (19) | 0.081 (2) | 0.0104 (16) | 0.0336 (17) | 0.0132 (18) |
C8 | 0.066 (2) | 0.067 (2) | 0.079 (2) | 0.0054 (16) | 0.0227 (17) | 0.0184 (17) |
C9 | 0.0550 (17) | 0.0561 (18) | 0.071 (2) | 0.0068 (14) | 0.0301 (16) | 0.0203 (15) |
C10 | 0.0429 (15) | 0.0698 (19) | 0.085 (2) | 0.0051 (13) | 0.0267 (15) | 0.0200 (16) |
C11 | 0.0365 (13) | 0.0570 (16) | 0.0650 (17) | 0.0033 (12) | 0.0200 (12) | 0.0083 (14) |
C12 | 0.0465 (16) | 0.0534 (16) | 0.082 (2) | 0.0024 (13) | 0.0152 (15) | 0.0128 (15) |
C13 | 0.092 (2) | 0.075 (2) | 0.075 (2) | −0.016 (2) | 0.0035 (19) | 0.0106 (18) |
C14 | 0.080 (2) | 0.059 (2) | 0.068 (2) | −0.0005 (17) | 0.0083 (17) | 0.0073 (17) |
C15 | 0.117 (3) | 0.073 (2) | 0.090 (3) | 0.010 (2) | 0.032 (2) | 0.013 (2) |
C16 | 0.140 (4) | 0.068 (3) | 0.107 (3) | 0.013 (2) | 0.027 (3) | 0.016 (2) |
C17 | 0.133 (4) | 0.089 (3) | 0.092 (3) | −0.004 (3) | 0.018 (3) | 0.034 (2) |
C18 | 0.153 (4) | 0.126 (4) | 0.097 (3) | 0.015 (3) | 0.060 (3) | 0.023 (3) |
C19 | 0.159 (4) | 0.084 (3) | 0.096 (3) | 0.026 (3) | 0.045 (3) | 0.012 (2) |
N1 | 0.0339 (12) | 0.0570 (14) | 0.0766 (17) | 0.0029 (11) | 0.0212 (11) | 0.0144 (12) |
O1 | 0.0800 (15) | 0.0640 (13) | 0.0849 (15) | 0.0187 (12) | 0.0356 (12) | 0.0125 (12) |
O2 | 0.0422 (11) | 0.0794 (14) | 0.1325 (19) | 0.0128 (10) | 0.0457 (12) | 0.0399 (13) |
C1—C2 | 1.511 (5) | C11—O2 | 1.234 (3) |
C1—H1A | 0.9600 | C11—N1 | 1.321 (3) |
C1—H1B | 0.9600 | C12—N1 | 1.441 (3) |
C1—H1C | 0.9600 | C12—C13 | 1.483 (4) |
C2—C7 | 1.389 (4) | C12—H12A | 0.9700 |
C2—C3 | 1.396 (5) | C12—H12B | 0.9700 |
C3—C4 | 1.369 (5) | C13—C14 | 1.504 (4) |
C3—H3 | 0.9300 | C13—H13A | 0.9700 |
C4—C5 | 1.372 (4) | C13—H13B | 0.9700 |
C4—H4 | 0.9300 | C14—C15 | 1.352 (5) |
C5—O1 | 1.375 (4) | C14—C19 | 1.377 (5) |
C5—C6 | 1.387 (4) | C15—C16 | 1.380 (5) |
C6—C7 | 1.386 (4) | C15—H15 | 0.9300 |
C6—C9 | 1.432 (4) | C16—C17 | 1.355 (6) |
C7—H7 | 0.9300 | C16—H16 | 0.9300 |
C8—C9 | 1.337 (4) | C17—C18 | 1.329 (6) |
C8—O1 | 1.378 (3) | C17—H17 | 0.9300 |
C8—H8 | 0.9300 | C18—C19 | 1.383 (6) |
C9—C10 | 1.493 (4) | C18—H18 | 0.9300 |
C10—C11 | 1.505 (4) | C19—H19 | 0.9300 |
C10—H10A | 0.9700 | N1—H1 | 0.79 (3) |
C10—H10B | 0.9700 | ||
C2—C1—H1A | 109.5 | O2—C11—C10 | 122.4 (2) |
C2—C1—H1B | 109.5 | N1—C11—C10 | 115.9 (2) |
H1A—C1—H1B | 109.5 | N1—C12—C13 | 114.3 (2) |
C2—C1—H1C | 109.5 | N1—C12—H12A | 108.7 |
H1A—C1—H1C | 109.5 | C13—C12—H12A | 108.7 |
H1B—C1—H1C | 109.5 | N1—C12—H12B | 108.7 |
C7—C2—C3 | 118.4 (4) | C13—C12—H12B | 108.7 |
C7—C2—C1 | 121.0 (3) | H12A—C12—H12B | 107.6 |
C3—C2—C1 | 120.6 (3) | C12—C13—C14 | 111.5 (3) |
C4—C3—C2 | 123.0 (3) | C12—C13—H13A | 109.3 |
C4—C3—H3 | 118.5 | C14—C13—H13A | 109.3 |
C2—C3—H3 | 118.5 | C12—C13—H13B | 109.3 |
C3—C4—C5 | 116.6 (3) | C14—C13—H13B | 109.3 |
C3—C4—H4 | 121.7 | H13A—C13—H13B | 108.0 |
C5—C4—H4 | 121.7 | C15—C14—C19 | 117.1 (3) |
C4—C5—O1 | 126.3 (3) | C15—C14—C13 | 121.1 (3) |
C4—C5—C6 | 123.5 (3) | C19—C14—C13 | 121.6 (3) |
O1—C5—C6 | 110.2 (3) | C14—C15—C16 | 121.4 (4) |
C7—C6—C5 | 118.3 (3) | C14—C15—H15 | 119.3 |
C7—C6—C9 | 135.4 (3) | C16—C15—H15 | 119.3 |
C5—C6—C9 | 106.2 (3) | C17—C16—C15 | 120.7 (4) |
C6—C7—C2 | 120.2 (3) | C17—C16—H16 | 119.7 |
C6—C7—H7 | 119.9 | C15—C16—H16 | 119.7 |
C2—C7—H7 | 119.9 | C18—C17—C16 | 118.8 (4) |
C9—C8—O1 | 112.9 (3) | C18—C17—H17 | 120.6 |
C9—C8—H8 | 123.5 | C16—C17—H17 | 120.6 |
O1—C8—H8 | 123.5 | C17—C18—C19 | 121.2 (4) |
C8—C9—C6 | 105.8 (3) | C17—C18—H18 | 119.4 |
C8—C9—C10 | 127.2 (3) | C19—C18—H18 | 119.4 |
C6—C9—C10 | 127.0 (3) | C14—C19—C18 | 120.7 (4) |
C9—C10—C11 | 114.2 (2) | C14—C19—H19 | 119.6 |
C9—C10—H10A | 108.7 | C18—C19—H19 | 119.6 |
C11—C10—H10A | 108.7 | C11—N1—C12 | 123.3 (2) |
C9—C10—H10B | 108.7 | C11—N1—H1 | 113 (2) |
C11—C10—H10B | 108.7 | C12—N1—H1 | 123 (2) |
H10A—C10—H10B | 107.6 | C5—O1—C8 | 104.9 (2) |
O2—C11—N1 | 121.6 (3) | ||
C7—C2—C3—C4 | 0.2 (5) | C6—C9—C10—C11 | 75.3 (4) |
C1—C2—C3—C4 | −179.6 (3) | C9—C10—C11—O2 | −4.8 (4) |
C2—C3—C4—C5 | 0.3 (5) | C9—C10—C11—N1 | 175.4 (3) |
C3—C4—C5—O1 | 179.8 (3) | N1—C12—C13—C14 | −170.0 (3) |
C3—C4—C5—C6 | −0.8 (5) | C12—C13—C14—C15 | −73.6 (4) |
C4—C5—C6—C7 | 0.9 (4) | C12—C13—C14—C19 | 101.9 (4) |
O1—C5—C6—C7 | −179.7 (2) | C19—C14—C15—C16 | −0.9 (6) |
C4—C5—C6—C9 | −178.9 (3) | C13—C14—C15—C16 | 174.9 (3) |
O1—C5—C6—C9 | 0.5 (3) | C14—C15—C16—C17 | −0.4 (7) |
C5—C6—C7—C2 | −0.3 (4) | C15—C16—C17—C18 | 1.8 (7) |
C9—C6—C7—C2 | 179.4 (3) | C16—C17—C18—C19 | −1.9 (8) |
C3—C2—C7—C6 | −0.2 (4) | C15—C14—C19—C18 | 0.7 (6) |
C1—C2—C7—C6 | 179.6 (3) | C13—C14—C19—C18 | −175.0 (4) |
O1—C8—C9—C6 | −0.5 (3) | C17—C18—C19—C14 | 0.7 (8) |
O1—C8—C9—C10 | −177.4 (2) | O2—C11—N1—C12 | 2.5 (4) |
C7—C6—C9—C8 | −179.8 (3) | C10—C11—N1—C12 | −177.7 (3) |
C5—C6—C9—C8 | 0.0 (3) | C13—C12—N1—C11 | 123.3 (3) |
C7—C6—C9—C10 | −2.8 (5) | C4—C5—O1—C8 | 178.6 (3) |
C5—C6—C9—C10 | 176.9 (3) | C6—C5—O1—C8 | −0.8 (3) |
C8—C9—C10—C11 | −108.4 (3) | C9—C8—O1—C5 | 0.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.79 (3) | 2.06 (3) | 2.849 (3) | 173 (3) |
Symmetry code: (i) x−1/2, −y+1/2, z. |
Acknowledgements
The authors thank the SAIF IIT Madras, Chennai, India, for the data collection.
References
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