organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

2-(5-Methyl-1-benzo­furan-3-yl)acetic acid

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aDepartment of Physics, Govt. First Grade College, Mulbagal, Kolar dist 563 131, Karnataka, India, bDepartment of Physics, Govt. College for Women, Kolar 563 101, Karnataka, India, cDepartment of Physics, Govt. College for Women, Mandya 571 401, India, and dDepartment of Chemistry, P.C. Jabin Science College, Hubli 580 031, Karnataka, India
*Correspondence e-mail: rkgowdaphy@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 January 2016; accepted 27 January 2016; online 3 February 2016)

The asymmetric unit of the title compound, C11H10O3, contains two crystallographically independent mol­ecules, A and B, with closely matching conformations (r.m.s. overlay fit = 0.105 Å). In each case, the OH group of the acetic acid residue occupies a position approximately anti­periplanar to the C atom of the heterocycle. A short intra­molecular C—H⋯O contact occurs within each mol­ecule. In the crystal, carb­oxy­lic acid A+B dimers generate R22(8) loops.

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

Structure description

Derivatives of 2,3-di­hydro-benzo­furanyl-3-acetic acids have been reported to be potent, selective and orally bioavailable G protein-coupled receptor 40 (GPR40) and free fatty acid receptor 1 agonists (FFA1) as glucose-dependent insulinotropic agents (Negoro et al. 2012[Negoro, N., Sasaki, S., Mikami, S., Ito, M., Tsujihata, Y., Ito, R., Suzuki, M., Takeuchi, K., Suzuki, N., Miyazaki, J., Santou, T., Odani, T., Kanzaki, N., Funami, M., Morohashi, A., Nonaka, M., Matsunaga, S., Yasuma, T. & Momose, Y. (2012). J. Med. Chem. 55, 3960-3974.]). As part of our studies in this area, we now report the synthesis and crystal structure of the title compound.

All the bond lengths and angles of the title mol­ecule are close to those observed for a similar structure (Gowda et al., 2015[Gowda, R., Gowda, K. V. A., Reddy, M. K. & Basanagouda, M. (2015). Acta Cryst. E71, o1053-o1054.]). The asymmetric unit of the title compound contains two crystallographically independent mol­ecules (C1–C11,O1–O3 and C12–C22,O4–O6), which are almost identical (Fig. 1[link]). In each molecule there is an intra­molecular C—H⋯O contact present (Table 1[link]). In the crystal, molecules are linked via pairs of O—H⋯O hydrogen bonds, forming AB dimers (Table 1[link] and Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O5i 0.82 1.83 2.650 (2) 176
O4—H4A⋯O2ii 0.82 1.90 2.715 (2) 179
C8—H8⋯O2 0.93 2.29 2.855 (3) 118
C19—H19⋯O5 0.93 2.29 2.843 (3) 118
Symmetry codes: (i) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing 40% probability displacement ellipsoids.
[Figure 2]
Figure 2
The crystal packing diagram of the title compound. The dotted lines indicate hydrogen bonds. All H atoms not involved in inter­actions have been omitted for clarity.

Synthesis and crystallization

6-Methyl-4-bromo­methyl­coumarin (10 mM) was refluxed in 1 M NaOH (100 ml) for 2 h (the completion of the reaction was monitored by TLC). The reaction mixture was cooled, neutralized with 1 M HCl and the obtained product was filtered and dried. Colourless blocks were obtained by recrystallization from an ethanol and ethyl acetate solvent mixture by slow evaporation technique (m.p. 370–371 K) (Basanagouda et al. 2015[Basanagouda, M., Narayanachari, 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.]).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C11H10O3
Mr 190.19
Crystal system, space group Monoclinic, P21/c
Temperature (K) 296
a, b, c (Å) 12.2090 (5), 20.3796 (14), 7.4335 (9)
β (°) 95.980 (4)
V3) 1839.5 (3)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.35 × 0.25 × 0.20
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA])
Tmin, Tmax 0.964, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections 21006, 3240, 2051
Rint 0.052
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.115, 1.02
No. of reflections 3240
No. of parameters 256
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.16, −0.16
Computer programs: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA]), SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA]), SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Bruno et al., 2002[Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

2-(5-Methyl-1-benzofuran-3-yl)acetic acid top
Crystal data top
C11H10O3Dx = 1.373 Mg m3
Mr = 190.19Melting point = 370–371 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.2090 (5) ÅCell parameters from 4172 reflections
b = 20.3796 (14) Åθ = 2.9–23.9°
c = 7.4335 (9) ŵ = 0.10 mm1
β = 95.980 (4)°T = 296 K
V = 1839.5 (3) Å3Block, colourless
Z = 80.35 × 0.25 × 0.20 mm
F(000) = 800
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3240 independent reflections
Radiation source: fine-focus sealed tube2051 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω and φ scanθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1414
Tmin = 0.964, Tmax = 0.989k = 2424
21006 measured reflectionsl = 88
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.4188P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115(Δ/σ)max = 0.003
S = 1.02Δρmax = 0.16 e Å3
3240 reflectionsΔρmin = 0.16 e Å3
256 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0026 (6)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.81759 (17)0.05868 (10)0.6079 (3)0.0399 (5)
C20.83597 (17)0.00743 (10)0.6377 (2)0.0396 (5)
H20.90590.02490.63150.048*
C30.75005 (16)0.04785 (10)0.6770 (2)0.0363 (5)
C40.64678 (17)0.02035 (11)0.6843 (3)0.0412 (5)
C50.62420 (18)0.04512 (11)0.6551 (3)0.0482 (6)
H50.55410.06230.66040.058*
C60.71189 (18)0.08378 (11)0.6174 (3)0.0467 (6)
H60.70010.12840.59760.056*
C70.73877 (17)0.11645 (10)0.7170 (3)0.0423 (5)
C80.63338 (19)0.12474 (11)0.7455 (3)0.0530 (6)
H80.60380.16490.77470.064*
C90.83049 (18)0.16488 (10)0.7216 (3)0.0539 (6)
H9A0.86600.15970.61170.065*
H9B0.88430.15360.82220.065*
C100.8017 (2)0.23539 (11)0.7389 (3)0.0493 (6)
C110.90915 (18)0.10371 (11)0.5656 (3)0.0508 (6)
H11A0.97880.08330.60190.076*
H11B0.90410.14430.63000.076*
H11C0.90290.11230.43800.076*
C120.66060 (18)0.20598 (11)0.0042 (3)0.0442 (5)
C130.76168 (19)0.23023 (11)0.0384 (3)0.0491 (6)
H130.76500.27300.08100.059*
C140.85690 (18)0.19330 (11)0.0201 (3)0.0497 (6)
H140.92410.21030.04640.060*
C150.84690 (17)0.13011 (11)0.0392 (3)0.0419 (5)
C160.74906 (16)0.10295 (10)0.0811 (2)0.0357 (5)
C170.65453 (17)0.14192 (10)0.0641 (3)0.0416 (5)
H170.58780.12490.09290.050*
C180.77211 (17)0.03530 (10)0.1269 (3)0.0376 (5)
C190.87940 (18)0.02707 (11)0.1095 (3)0.0472 (6)
H190.91630.01260.13010.057*
C200.68777 (17)0.01216 (10)0.1778 (3)0.0425 (5)
H20A0.65950.00390.28670.051*
H20B0.62710.01200.08260.051*
C210.72311 (19)0.08114 (10)0.2101 (3)0.0430 (5)
C220.56094 (19)0.24951 (12)0.0157 (3)0.0616 (7)
H22A0.49620.22330.04490.092*
H22B0.56770.28070.11070.092*
H22C0.55520.27240.09580.092*
O10.88003 (13)0.27454 (8)0.6973 (3)0.0706 (5)
H1A0.85800.31260.69580.085*
O20.71609 (14)0.25546 (8)0.7889 (2)0.0660 (5)
O30.57310 (12)0.06757 (7)0.7271 (2)0.0544 (4)
O40.64091 (12)0.11960 (7)0.2445 (2)0.0620 (5)
H4A0.66310.15750.25740.074*
O50.81643 (13)0.10129 (7)0.2076 (2)0.0623 (5)
O60.92925 (11)0.08380 (7)0.0578 (2)0.0516 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0400 (13)0.0407 (13)0.0390 (11)0.0006 (10)0.0046 (9)0.0054 (10)
C20.0330 (12)0.0421 (13)0.0442 (12)0.0009 (10)0.0059 (9)0.0025 (10)
C30.0330 (12)0.0402 (12)0.0355 (11)0.0001 (10)0.0024 (9)0.0034 (9)
C40.0346 (13)0.0455 (14)0.0441 (12)0.0026 (11)0.0064 (10)0.0047 (10)
C50.0376 (13)0.0485 (15)0.0587 (14)0.0076 (11)0.0061 (11)0.0026 (11)
C60.0496 (14)0.0378 (13)0.0531 (13)0.0053 (11)0.0072 (11)0.0012 (10)
C70.0357 (13)0.0402 (13)0.0507 (13)0.0037 (10)0.0036 (10)0.0015 (10)
C80.0468 (15)0.0422 (14)0.0704 (16)0.0037 (12)0.0085 (12)0.0026 (12)
C90.0419 (14)0.0412 (14)0.0791 (16)0.0035 (11)0.0081 (12)0.0046 (12)
C100.0429 (14)0.0405 (14)0.0645 (15)0.0001 (12)0.0060 (12)0.0029 (11)
C110.0501 (14)0.0413 (13)0.0622 (14)0.0046 (11)0.0113 (11)0.0004 (11)
C120.0468 (14)0.0434 (13)0.0422 (12)0.0026 (11)0.0040 (10)0.0003 (10)
C130.0588 (16)0.0400 (13)0.0493 (13)0.0039 (12)0.0096 (11)0.0025 (10)
C140.0431 (14)0.0505 (15)0.0564 (14)0.0101 (12)0.0099 (11)0.0013 (11)
C150.0365 (13)0.0466 (14)0.0429 (12)0.0016 (11)0.0048 (10)0.0043 (10)
C160.0358 (12)0.0389 (12)0.0324 (11)0.0026 (10)0.0032 (9)0.0027 (9)
C170.0374 (13)0.0454 (13)0.0425 (12)0.0015 (10)0.0070 (10)0.0011 (10)
C180.0360 (13)0.0394 (13)0.0375 (11)0.0003 (10)0.0039 (9)0.0033 (9)
C190.0458 (15)0.0405 (14)0.0552 (14)0.0004 (11)0.0056 (11)0.0002 (11)
C200.0422 (13)0.0413 (13)0.0442 (12)0.0015 (10)0.0060 (10)0.0015 (10)
C210.0407 (14)0.0402 (13)0.0478 (13)0.0034 (12)0.0029 (10)0.0051 (10)
C220.0600 (16)0.0539 (15)0.0712 (17)0.0101 (13)0.0086 (13)0.0099 (13)
O10.0501 (10)0.0396 (10)0.1260 (15)0.0026 (8)0.0271 (10)0.0054 (9)
O20.0561 (11)0.0432 (10)0.1032 (14)0.0048 (9)0.0294 (10)0.0024 (9)
O30.0375 (9)0.0498 (10)0.0772 (11)0.0027 (8)0.0120 (8)0.0010 (8)
O40.0472 (10)0.0385 (9)0.1025 (13)0.0004 (8)0.0182 (9)0.0061 (9)
O50.0395 (10)0.0424 (10)0.1051 (13)0.0036 (8)0.0082 (9)0.0007 (9)
O60.0374 (9)0.0500 (10)0.0683 (10)0.0018 (8)0.0103 (7)0.0005 (8)
Geometric parameters (Å, º) top
C1—C21.380 (3)C12—C131.396 (3)
C1—C61.397 (3)C12—C221.501 (3)
C1—C111.505 (3)C13—C141.380 (3)
C2—C31.388 (3)C13—H130.9300
C2—H20.9300C14—C151.371 (3)
C3—C41.386 (3)C14—H140.9300
C3—C71.439 (3)C15—O61.375 (2)
C4—C51.375 (3)C15—C161.381 (3)
C4—O31.377 (2)C16—C171.396 (3)
C5—C61.381 (3)C16—C181.441 (3)
C5—H50.9300C17—H170.9300
C6—H60.9300C18—C191.340 (3)
C7—C81.336 (3)C18—C201.490 (3)
C7—C91.490 (3)C19—O61.380 (2)
C8—O31.377 (3)C19—H190.9300
C8—H80.9300C20—C211.483 (3)
C9—C101.488 (3)C20—H20A0.9700
C9—H9A0.9700C20—H20B0.9700
C9—H9B0.9700C21—O51.213 (2)
C10—O21.216 (2)C21—O41.319 (2)
C10—O11.307 (3)C22—H22A0.9600
C11—H11A0.9600C22—H22B0.9600
C11—H11B0.9600C22—H22C0.9600
C11—H11C0.9600O1—H1A0.8200
C12—C171.384 (3)O4—H4A0.8200
C2—C1—C6119.0 (2)C13—C12—C22119.7 (2)
C2—C1—C11121.14 (19)C14—C13—C12122.7 (2)
C6—C1—C11119.8 (2)C14—C13—H13118.7
C1—C2—C3119.95 (19)C12—C13—H13118.7
C1—C2—H2120.0C15—C14—C13116.2 (2)
C3—C2—H2120.0C15—C14—H14121.9
C4—C3—C2118.60 (19)C13—C14—H14121.9
C4—C3—C7106.12 (18)C14—C15—O6126.0 (2)
C2—C3—C7135.3 (2)C14—C15—C16123.9 (2)
C5—C4—O3126.13 (19)O6—C15—C16110.04 (19)
C5—C4—C3123.7 (2)C15—C16—C17118.54 (19)
O3—C4—C3110.20 (18)C15—C16—C18106.53 (18)
C4—C5—C6116.0 (2)C17—C16—C18134.85 (19)
C4—C5—H5122.0C12—C17—C16119.64 (19)
C6—C5—H5122.0C12—C17—H17120.2
C5—C6—C1122.8 (2)C16—C17—H17120.2
C5—C6—H6118.6C19—C18—C16105.42 (18)
C1—C6—H6118.6C19—C18—C20130.66 (19)
C8—C7—C3105.67 (19)C16—C18—C20123.91 (18)
C8—C7—C9130.2 (2)C18—C19—O6112.70 (19)
C3—C7—C9124.08 (19)C18—C19—H19123.6
C7—C8—O3113.0 (2)O6—C19—H19123.6
C7—C8—H8123.5C21—C20—C18117.34 (18)
O3—C8—H8123.5C21—C20—H20A108.0
C10—C9—C7117.23 (19)C18—C20—H20A108.0
C10—C9—H9A108.0C21—C20—H20B108.0
C7—C9—H9A108.0C18—C20—H20B108.0
C10—C9—H9B108.0H20A—C20—H20B107.2
C7—C9—H9B108.0O5—C21—O4122.4 (2)
H9A—C9—H9B107.2O5—C21—C20125.2 (2)
O2—C10—O1122.7 (2)O4—C21—C20112.35 (19)
O2—C10—C9124.7 (2)C12—C22—H22A109.5
O1—C10—C9112.5 (2)C12—C22—H22B109.5
C1—C11—H11A109.5H22A—C22—H22B109.5
C1—C11—H11B109.5C12—C22—H22C109.5
H11A—C11—H11B109.5H22A—C22—H22C109.5
C1—C11—H11C109.5H22B—C22—H22C109.5
H11A—C11—H11C109.5C10—O1—H1A109.5
H11B—C11—H11C109.5C4—O3—C8105.01 (16)
C17—C12—C13119.0 (2)C21—O4—H4A109.5
C17—C12—C22121.3 (2)C15—O6—C19105.31 (16)
C6—C1—C2—C30.2 (3)C13—C14—C15—O6176.28 (18)
C11—C1—C2—C3179.80 (17)C13—C14—C15—C160.5 (3)
C1—C2—C3—C40.3 (3)C14—C15—C16—C170.6 (3)
C1—C2—C3—C7179.0 (2)O6—C15—C16—C17177.81 (16)
C2—C3—C4—C50.1 (3)C14—C15—C16—C18176.63 (19)
C7—C3—C4—C5179.39 (19)O6—C15—C16—C180.6 (2)
C2—C3—C4—O3179.20 (16)C13—C12—C17—C160.1 (3)
C7—C3—C4—O30.3 (2)C22—C12—C17—C16179.93 (18)
O3—C4—C5—C6178.69 (18)C15—C16—C17—C120.8 (3)
C3—C4—C5—C60.2 (3)C18—C16—C17—C12175.5 (2)
C4—C5—C6—C10.4 (3)C15—C16—C18—C190.0 (2)
C2—C1—C6—C50.2 (3)C17—C16—C18—C19176.6 (2)
C11—C1—C6—C5179.81 (19)C15—C16—C18—C20178.94 (17)
C4—C3—C7—C80.4 (2)C17—C16—C18—C202.4 (3)
C2—C3—C7—C8179.0 (2)C16—C18—C19—O60.6 (2)
C4—C3—C7—C9179.34 (19)C20—C18—C19—O6179.43 (18)
C2—C3—C7—C91.3 (4)C19—C18—C20—C212.4 (3)
C3—C7—C8—O30.3 (2)C16—C18—C20—C21176.29 (17)
C9—C7—C8—O3179.4 (2)C18—C20—C21—O54.1 (3)
C8—C7—C9—C108.2 (4)C18—C20—C21—O4176.54 (17)
C3—C7—C9—C10171.4 (2)C5—C4—O3—C8179.2 (2)
C7—C9—C10—O217.1 (4)C3—C4—O3—C80.2 (2)
C7—C9—C10—O1164.1 (2)C7—C8—O3—C40.1 (2)
C17—C12—C13—C141.3 (3)C14—C15—O6—C19176.2 (2)
C22—C12—C13—C14178.77 (19)C16—C15—O6—C190.9 (2)
C12—C13—C14—C151.5 (3)C18—C19—O6—C150.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O5i0.821.832.650 (2)176
O4—H4A···O2ii0.821.902.715 (2)179
C8—H8···O20.932.292.855 (3)118
C19—H19···O50.932.292.843 (3)118
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y1/2, z1/2.
 

Acknowledgements

MB thanks UGC–SWRO, Bangalore, for providing a Minor Research Project (reference No. 1415-MRP/14–15/KAKA067/UGC-SWRO, Diary No. 1709). The authors also thank the SAIF IIT Madras, Chennai, for the data collection.

References

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