2-(6-Methyl-1-benzo­furan-3-yl)acetic acid

Ramprasad, N.; Gowda, K.V.A.; Gowda, R.; Basanagouda, M.; Kantharaj, K.S.; Gowda, G.V.J.

doi:10.1107/S2414314616014346

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 9| September 2016| x161434

doi:10.1107/S2414314616014346

Open

access

2-(6-Methyl-1-benzofuran-3-yl)acetic acid

N. Ramprasad,^a K. V. Arjuna Gowda,^b ^* Ramakrishna Gowda,^c Mahantesha Basanagouda,^d K. S. Kantharaj ^e and G. V. Jagadeesha Gowda ^f

^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 H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 2 September 2016; accepted 9 September 2016; online 27 September 2016)

The asymmetric unit of the title compound, C₁₁H₁₀O₃, contains two crystallographically independent molecules (A and B) with nearly matching conformations. Both molecules are almost planar [r.m.s. overlay fit for the non-hydrogen atoms = 0.011 (1) Å] and in each molecule there is a short intramolecular C—H⋯O contact. In both molecules, the OH group of the acetic acid residue occupies a position approximately antiperiplanar to the C atom of the heterocycle. In the crystal, the two molecules are linked by a pair of O—H⋯O hydrogen bonds, enclosing an R²₂(8) ring motif and forming an A–B dimer. The dimers are linked by C—H⋯π interactions, forming columns along the [010] direction.

Keywords: crystal structure; benzofuran; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1484421

Structure description

Benzofuran derivatives have occupied an important place among various heterocycles by virtue of their involvement in medicinal chemistry and drug discovery (Hiremathad et al., 2015 ). Carboxylic acids such as arylalkanoic acids exhibit interesting anti-inflammatory, analgesic and antipyretic properties, and so have been in wide clinical use for a number of years (Basanagouda et al. 2015 ).

The asymmetric unit of the title compound contains two crystallographically independent molecules (A = C1–C11/O1–O3 and B = C12–C22/O4–O6), which are almost identical (Fig. 1). Both molecules are almost planar with an r.m.s. overlay fit for the non-hydrogen atoms of 0.011 (1) Å. In each molecule there is a short intramolecular C—H⋯O contact present (Table 1). The bond lengths and angles of the title molecules are close to those observed for similar structures, viz. 2-(5-methoxy-1-benzofuran-3-yl)acetic acid (Gowda et al., 2015 ) and 2-(5-methyl-1-benzofuran-3-yl)acetic acid (Ramprasad et al., 2016 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroid of rings C4–C9 and C15–C20, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5	0.82	1.90	2.7144 (15)	174
O4—H4⋯O2	0.82	1.83	2.6432 (15)	175
C10—H10⋯O2	0.93	2.25	2.813 (2)	118
C21—H21⋯O5	0.93	2.37	2.916 (2)	117
C2—H2A⋯Cg1ⁱ	0.97	2.88	3.5629 (18)	128
C11—H11A⋯Cg1ⁱⁱ	0.96	2.95	3.733 (2)	140
C13—H13B⋯Cg2ⁱⁱ	0.97	2.86	3.5233 (17)	126
C22—H22C⋯Cg2ⁱ	0.96	2.77	3.6955 (18)	162
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Figure 1
The molecular structure of the two independent molecules of the title compound, with atom labelling and 40% probability displacement ellipsoids. Figure 1 should show the O—H⋯O hydrogen bonds

In the crystal, the molecules are linked by a pair of O—H⋯O hydrogen bonds, enclosing an $[R_{2}^{2}]$ (8), ring motif and forming an A–B dimer (Fig. 2 and Table 1). The dimers are linked by C—H⋯π interactions forming columns along the [010] direction; see Table 1.

Figure 2
The crystal packing of the title compound, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1

Synthesis and crystallization

The title compound was synthesized according to a reported procedure (Basanagouda et al., 2015). 7-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. Pale-yellow block-like crystals were obtained by recrystallization from an ethanol and ethyl acetate solvent mixture by slow evaporation (m.p. 378–379 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₁₀O₃
M_r	190.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	26.2392 (8), 5.1197 (1), 14.2546 (4)
β (°)	103.826 (1)
V (Å³)	1859.43 (9)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.95, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	41449, 3665, 2898
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.115, 1.02
No. of reflections	3665
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19
Computer programs: APEX2, SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1994 ), SHELXL2014 (Sheldrick, 2015 ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 1484421

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S2414314616014346/su4070sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616014346/su4070Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616014346/su4070Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(I) top

Crystal data top

C₁₁H₁₀O₃	F(000) = 800
M_r = 190.19	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.2392 (8) Å	Cell parameters from 9885 reflections
b = 5.1197 (1) Å	θ = 2.9–25.3°
c = 14.2546 (4) Å	µ = 0.10 mm⁻¹
β = 103.826 (1)°	T = 296 K
V = 1859.43 (9) Å³	Block, pale-yellow
Z = 8	0.30 × 0.25 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2898 reflections with I > 2σ(I)
Radiation source: Sealed tube	R_int = 0.030
ω and φ scan	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −32→32
T_min = 0.95, T_max = 0.98	k = −6→6
41449 measured reflections	l = −17→17
3665 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0566P)² + 0.5754P] where P = (F_o² + 2F_c²)/3
3665 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

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

	x	y	z	U_iso*/U_eq
C1	0.27076 (6)	0.7110 (3)	0.91891 (11)	0.0411 (4)
C2	0.29455 (6)	0.9059 (3)	0.86353 (11)	0.0450 (4)
H2A	0.3111	0.8109	0.8198	0.054*
H2B	0.2664	1.0089	0.8242	0.054*
C3	0.33414 (6)	1.0892 (3)	0.92134 (10)	0.0402 (4)
C4	0.36445 (6)	1.2734 (3)	0.88026 (11)	0.0420 (4)
C5	0.36823 (7)	1.3405 (4)	0.78736 (12)	0.0535 (4)
H5	0.3472	1.2593	0.7334	0.064*
C6	0.40388 (7)	1.5306 (4)	0.77748 (13)	0.0596 (5)
H6	0.4065	1.5762	0.7156	0.072*
C7	0.43625 (7)	1.6574 (4)	0.85653 (14)	0.0540 (4)
C8	0.43251 (7)	1.5924 (4)	0.94871 (14)	0.0554 (5)
H8	0.4533	1.6738	1.0028	0.067*
C9	0.39674 (6)	1.4024 (4)	0.95759 (11)	0.0469 (4)
C10	0.35008 (7)	1.1210 (4)	1.01690 (12)	0.0508 (4)
H10	0.3368	1.0255	1.0613	0.061*
C11	0.47501 (8)	1.8610 (4)	0.84131 (18)	0.0741 (6)
H11A	0.4714	2.0151	0.8775	0.111*
H11B	0.4683	1.9036	0.7739	0.111*
H11C	0.5100	1.7938	0.8628	0.111*
O1	0.23573 (5)	0.5612 (2)	0.86242 (8)	0.0542 (3)
H1	0.2237	0.4577	0.8955	0.081*
O2	0.28234 (5)	0.6905 (2)	1.00640 (8)	0.0518 (3)
O3	0.38825 (5)	1.3103 (3)	1.04283 (8)	0.0594 (3)
C12	0.21368 (6)	0.1683 (3)	1.05349 (11)	0.0386 (3)
C13	0.19482 (6)	−0.0334 (3)	1.11280 (10)	0.0419 (4)
H13A	0.2247	−0.1402	1.1435	0.050*
H13B	0.1831	0.0563	1.1638	0.050*
C14	0.15189 (6)	−0.2120 (3)	1.06360 (10)	0.0374 (3)
C15	0.12797 (6)	−0.4013 (3)	1.11542 (10)	0.0350 (3)
C16	0.13567 (6)	−0.4802 (3)	1.21139 (10)	0.0394 (3)
H16	0.1619	−0.4053	1.2595	0.047*
C17	0.10345 (6)	−0.6724 (3)	1.23336 (10)	0.0413 (4)
H17	0.1087	−0.7270	1.2972	0.050*
C18	0.06324 (6)	−0.7879 (3)	1.16331 (11)	0.0402 (3)
C19	0.05549 (6)	−0.7099 (3)	1.06785 (11)	0.0453 (4)
H19	0.0290	−0.7826	1.0197	0.054*
C20	0.08840 (6)	−0.5213 (3)	1.04675 (10)	0.0409 (4)
C21	0.12600 (7)	−0.2342 (4)	0.97102 (11)	0.0498 (4)
H21	0.1336	−0.1348	0.9214	0.060*
C22	0.02904 (7)	−0.9954 (3)	1.19135 (13)	0.0508 (4)
H22A	−0.0071	−0.9579	1.1620	0.076*
H22B	0.0343	−0.9980	1.2603	0.076*
H22C	0.0381	−1.1626	1.1695	0.076*
O4	0.24869 (4)	0.3244 (2)	1.10770 (8)	0.0502 (3)
H4	0.2582	0.4340	1.0735	0.075*
O5	0.19955 (5)	0.1894 (2)	0.96586 (8)	0.0491 (3)
O6	0.08679 (5)	−0.4203 (3)	0.95682 (7)	0.0548 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0426 (8)	0.0394 (8)	0.0417 (8)	0.0048 (7)	0.0105 (7)	0.0023 (7)
C2	0.0506 (9)	0.0463 (9)	0.0383 (8)	−0.0032 (7)	0.0110 (7)	0.0034 (7)
C3	0.0392 (8)	0.0435 (8)	0.0381 (8)	0.0042 (7)	0.0095 (6)	0.0026 (6)
C4	0.0398 (8)	0.0444 (9)	0.0418 (8)	0.0015 (7)	0.0095 (6)	−0.0005 (7)
C5	0.0582 (10)	0.0605 (11)	0.0415 (9)	−0.0127 (9)	0.0113 (8)	0.0008 (8)
C6	0.0613 (11)	0.0670 (12)	0.0530 (10)	−0.0115 (10)	0.0185 (9)	0.0044 (9)
C7	0.0424 (9)	0.0512 (10)	0.0699 (12)	−0.0024 (8)	0.0167 (8)	0.0000 (9)
C8	0.0428 (9)	0.0594 (11)	0.0613 (11)	−0.0052 (8)	0.0068 (8)	−0.0118 (9)
C9	0.0409 (8)	0.0555 (10)	0.0435 (9)	0.0017 (7)	0.0084 (7)	−0.0018 (7)
C10	0.0489 (9)	0.0616 (11)	0.0413 (8)	−0.0057 (8)	0.0096 (7)	0.0023 (8)
C11	0.0583 (12)	0.0636 (13)	0.1043 (17)	−0.0143 (10)	0.0275 (11)	0.0002 (12)
O1	0.0595 (7)	0.0548 (7)	0.0449 (6)	−0.0142 (6)	0.0061 (5)	0.0064 (5)
O2	0.0627 (7)	0.0525 (7)	0.0401 (6)	−0.0085 (6)	0.0123 (5)	0.0049 (5)
O3	0.0568 (7)	0.0776 (9)	0.0407 (6)	−0.0113 (7)	0.0057 (5)	−0.0041 (6)
C12	0.0412 (8)	0.0369 (8)	0.0393 (8)	0.0051 (6)	0.0126 (6)	0.0023 (6)
C13	0.0520 (9)	0.0393 (8)	0.0368 (8)	−0.0002 (7)	0.0151 (7)	0.0016 (6)
C14	0.0448 (8)	0.0354 (8)	0.0349 (7)	0.0048 (6)	0.0155 (6)	0.0017 (6)
C15	0.0386 (7)	0.0342 (7)	0.0340 (7)	0.0037 (6)	0.0119 (6)	−0.0009 (6)
C16	0.0436 (8)	0.0436 (8)	0.0312 (7)	−0.0017 (7)	0.0093 (6)	−0.0021 (6)
C17	0.0502 (9)	0.0441 (9)	0.0320 (7)	−0.0005 (7)	0.0144 (6)	0.0012 (6)
C18	0.0433 (8)	0.0374 (8)	0.0433 (8)	0.0017 (7)	0.0171 (7)	−0.0024 (6)
C19	0.0460 (9)	0.0474 (9)	0.0406 (8)	−0.0061 (7)	0.0065 (7)	−0.0055 (7)
C20	0.0468 (8)	0.0456 (9)	0.0302 (7)	0.0031 (7)	0.0089 (6)	0.0015 (6)
C21	0.0604 (10)	0.0518 (10)	0.0387 (8)	−0.0042 (8)	0.0148 (7)	0.0087 (7)
C22	0.0545 (10)	0.0444 (9)	0.0579 (10)	−0.0066 (8)	0.0222 (8)	−0.0023 (8)
O4	0.0555 (7)	0.0508 (7)	0.0439 (6)	−0.0107 (6)	0.0110 (5)	0.0048 (5)
O5	0.0591 (7)	0.0481 (7)	0.0401 (6)	−0.0065 (6)	0.0118 (5)	0.0067 (5)
O6	0.0644 (7)	0.0654 (8)	0.0308 (6)	−0.0123 (6)	0.0041 (5)	0.0061 (5)

Geometric parameters (Å, º) top

C1—O2	1.2156 (18)	C12—O5	1.2199 (17)
C1—O1	1.3143 (19)	C12—O4	1.3195 (19)
C1—C2	1.498 (2)	C12—C13	1.492 (2)
C2—C3	1.493 (2)	C13—C14	1.490 (2)
C2—H2A	0.9700	C13—H13A	0.9700
C2—H2B	0.9700	C13—H13B	0.9700
C3—C10	1.336 (2)	C14—C21	1.337 (2)
C3—C4	1.445 (2)	C14—C15	1.449 (2)
C4—C9	1.387 (2)	C15—C20	1.389 (2)
C4—C5	1.394 (2)	C15—C16	1.3939 (19)
C5—C6	1.380 (2)	C16—C17	1.381 (2)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.398 (3)	C17—C18	1.399 (2)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.381 (3)	C18—C19	1.386 (2)
C7—C11	1.508 (3)	C18—C22	1.505 (2)
C8—C9	1.378 (2)	C19—C20	1.376 (2)
C8—H8	0.9300	C19—H19	0.9300
C9—O3	1.3703 (19)	C20—O6	1.3736 (17)
C10—O3	1.379 (2)	C21—O6	1.381 (2)
C10—H10	0.9300	C21—H21	0.9300
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600
O1—H1	0.8200	O4—H4	0.8200

O2—C1—O1	123.02 (15)	O5—C12—O4	123.00 (14)
O2—C1—C2	124.38 (15)	O5—C12—C13	125.51 (14)
O1—C1—C2	112.59 (13)	O4—C12—C13	111.48 (12)
C3—C2—C1	116.77 (13)	C14—C13—C12	118.29 (13)
C3—C2—H2A	108.1	C14—C13—H13A	107.7
C1—C2—H2A	108.1	C12—C13—H13A	107.7
C3—C2—H2B	108.1	C14—C13—H13B	107.7
C1—C2—H2B	108.1	C12—C13—H13B	107.7
H2A—C2—H2B	107.3	H13A—C13—H13B	107.1
C10—C3—C4	105.38 (14)	C21—C14—C15	105.47 (14)
C10—C3—C2	130.26 (15)	C21—C14—C13	131.71 (14)
C4—C3—C2	124.35 (13)	C15—C14—C13	122.78 (13)
C9—C4—C5	117.98 (15)	C20—C15—C16	118.18 (14)
C9—C4—C3	106.24 (14)	C20—C15—C14	106.17 (12)
C5—C4—C3	135.78 (15)	C16—C15—C14	135.65 (14)
C6—C5—C4	118.32 (16)	C17—C16—C15	118.42 (14)
C6—C5—H5	120.8	C17—C16—H16	120.8
C4—C5—H5	120.8	C15—C16—H16	120.8
C5—C6—C7	122.75 (17)	C16—C17—C18	122.52 (14)
C5—C6—H6	118.6	C16—C17—H17	118.7
C7—C6—H6	118.6	C18—C17—H17	118.7
C8—C7—C6	119.16 (17)	C19—C18—C17	119.20 (14)
C8—C7—C11	120.47 (18)	C19—C18—C22	120.47 (14)
C6—C7—C11	120.37 (18)	C17—C18—C22	120.33 (14)
C9—C8—C7	117.52 (16)	C20—C19—C18	117.67 (14)
C9—C8—H8	121.2	C20—C19—H19	121.2
C7—C8—H8	121.2	C18—C19—H19	121.2
O3—C9—C8	125.65 (16)	O6—C20—C19	125.98 (14)
O3—C9—C4	110.07 (15)	O6—C20—C15	110.01 (13)
C8—C9—C4	124.28 (16)	C19—C20—C15	123.99 (13)
C3—C10—O3	112.90 (15)	C14—C21—O6	112.83 (14)
C3—C10—H10	123.5	C14—C21—H21	123.6
O3—C10—H10	123.5	O6—C21—H21	123.6
C7—C11—H11A	109.5	C18—C22—H22A	109.5
C7—C11—H11B	109.5	C18—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
C7—C11—H11C	109.5	C18—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5
C1—O1—H1	109.5	C12—O4—H4	109.5
C9—O3—C10	105.41 (12)	C20—O6—C21	105.51 (12)

O2—C1—C2—C3	−1.5 (2)	O5—C12—C13—C14	−5.5 (2)
O1—C1—C2—C3	178.84 (14)	O4—C12—C13—C14	175.09 (13)
C1—C2—C3—C10	−4.8 (3)	C12—C13—C14—C21	1.9 (3)
C1—C2—C3—C4	174.18 (14)	C12—C13—C14—C15	−175.21 (13)
C10—C3—C4—C9	−0.01 (18)	C21—C14—C15—C20	−0.51 (17)
C2—C3—C4—C9	−179.25 (15)	C13—C14—C15—C20	177.27 (14)
C10—C3—C4—C5	179.0 (2)	C21—C14—C15—C16	179.70 (17)
C2—C3—C4—C5	−0.2 (3)	C13—C14—C15—C16	−2.5 (3)
C9—C4—C5—C6	0.2 (3)	C20—C15—C16—C17	−0.4 (2)
C3—C4—C5—C6	−178.79 (18)	C14—C15—C16—C17	179.42 (15)
C4—C5—C6—C7	0.1 (3)	C15—C16—C17—C18	−0.7 (2)
C5—C6—C7—C8	−0.4 (3)	C16—C17—C18—C19	0.7 (2)
C5—C6—C7—C11	179.15 (18)	C16—C17—C18—C22	−179.62 (14)
C6—C7—C8—C9	0.4 (3)	C17—C18—C19—C20	0.3 (2)
C11—C7—C8—C9	−179.20 (16)	C22—C18—C19—C20	−179.35 (14)
C7—C8—C9—O3	178.90 (16)	C18—C19—C20—O6	179.90 (14)
C7—C8—C9—C4	0.0 (3)	C18—C19—C20—C15	−1.4 (2)
C5—C4—C9—O3	−179.32 (15)	C16—C15—C20—O6	−179.69 (13)
C3—C4—C9—O3	−0.06 (18)	C14—C15—C20—O6	0.48 (17)
C5—C4—C9—C8	−0.2 (3)	C16—C15—C20—C19	1.4 (2)
C3—C4—C9—C8	179.03 (16)	C14—C15—C20—C19	−178.39 (15)
C4—C3—C10—O3	0.08 (19)	C15—C14—C21—O6	0.37 (19)
C2—C3—C10—O3	179.25 (15)	C13—C14—C21—O6	−177.13 (15)
C8—C9—O3—C10	−178.97 (17)	C19—C20—O6—C21	178.57 (16)
C4—C9—O3—C10	0.11 (18)	C15—C20—O6—C21	−0.27 (18)
C3—C10—O3—C9	−0.12 (19)	C14—C21—O6—C20	−0.08 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroid of rings C4–C9 and C15–C20, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.82	1.90	2.7144 (15)	174
O4—H4···O2	0.82	1.83	2.6432 (15)	175
C10—H10···O2	0.93	2.25	2.813 (2)	118
C21—H21···O5	0.93	2.37	2.916 (2)	117
C2—H2A···Cg1ⁱ	0.97	2.88	3.5629 (18)	128
C11—H11A···Cg1ⁱⁱ	0.96	2.95	3.733 (2)	140
C13—H13B···Cg2ⁱⁱ	0.97	2.86	3.5233 (17)	126
C22—H22C···Cg2ⁱ	0.96	2.77	3.6955 (18)	162

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

Acknowledgements

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

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
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. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gowda, R., Gowda, K. V. A., Reddy, M. K. & Basanagouda, M. (2015). Acta Cryst. E71, o1053–o1054. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hiremathad, A., Patil, M. R. Chethana, K. R., Chand, K., Santos, M. A. & Keri, R. S. (2015). RSC Adv. 5, 96809–96828. CrossRef CAS Google Scholar
Ramprasad, N., Gowda, R., Gowda, K. V. A. & Basanagouda, M. (2016). IUCrData, 1, x160170. Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 9| September 2016| x161434

doi:10.1107/S2414314616014346

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

2-(6-Methyl-1-benzo­furan-3-yl)acetic acid

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

2-(6-Methyl-1-benzofuran-3-yl)acetic acid