Crystal structure of 2-(5-meth­oxy-1-benzo­furan-3-yl)acetic acid

Gowda, R.; Gowda, K.V.A.; Reddy, M.K.; Basanagouda, M.

doi:10.1107/S2056989015023609

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o1053-o1054

https://doi.org/10.1107/S2056989015023609

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Crystal structure of 2-(5-methoxy-1-benzofuran-3-yl)acetic acid

Ramakrishna Gowda,^a ^* K. V. Arjuna Gowda,^b M. Keshava Reddy ^c and Mahantesha Basanagouda ^d

^aDepartment of Physics, Govt. College for Women, Kolar 563 101, Karnataka, India, ^bDepartment of Physics, Govt. College for Women, Mandya 571 401, Karnataka, India, ^cDepartment of Physics, Govt. PU College, Jayanagara, Bangalore 560 011, Karnataka, India, and ^dDepartment of Chemistry, P.C. Jabin Science College, Hubli 580 031, Karnataka, India
^*Correspondence e-mail: rkgowdaphy@gmail.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 6 December 2015; accepted 9 December 2015; online 16 December 2015)

The benzofuran residue in the title compound, C₁₁H₁₀O₄, is essentially planar (the r.m.s. deviation for the nine non-H atoms = 0.011 Å). While the methoxy group is coplanar with the fused ring system [C—C—O—C torsion angle = 3.1 (3)°], the acetic acid residue occupies a position almost prime [C—C—C—C = 77.0 (2)°]. In the crystal, centrosymmetrically related molecules are linked by O—H⋯O hydrogen bonds to form eight-membered {⋯HOCO}₂ synthons. The dimeric aggregates assemble into supramolecular layers in the ab plane via benzene-C—H⋯O(ring) interactions.

Keywords: crystal structure; benzofuran; hydrogen bonding.

CCDC reference: 1401314

1. Related literature

For a related structures and background to benzofurans and their applications, see: Dawood (2013 ); Khanam & Shamsuzzaman (2015 ); Radadiya & Shah (2015 ); Naik et al. (2015 ); Nevagi et al. (2015 ). For the synthesis, see: Basanagouda et al. (2015 ).

2. Experimental

2.1. Crystal data

C₁₁H₁₀O₄
M_r = 206.19
Monoclinic, P 2₁ /c
a = 5.8096 (3) Å
b = 13.2034 (5) Å
c = 12.5738 (6) Å
β = 97.641 (3)°
V = 955.93 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.35 × 0.30 × 0.25 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.961, T_max = 0.979
12813 measured reflections
2094 independent reflections
1621 reflections with I > 2σ(I)
R_int = 0.024

2.3. Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.12
2094 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.82	2.6357 (17)	174
C2—H2⋯O4ⁱⁱ	0.93	2.55	3.4629 (19)	169
Symmetry codes: (i) -x, -y+2, -z+2; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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 ) and Mercury (Bruno et al., 2002 ); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1401314

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015023609/tk5414sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023609/tk5414Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015023609/tk5414Isup3.cml

checkCIF report

Comment top

Benzofuran scaffolds have drawn considerable attention due to their physiological and chemotherapeutic properties as well as their widespread occurrence in nature. They display potent biological properties including antihyperglycemic, analgesic, antiparasitic, antimicrobial, antitumor and kinase inhibitor activities (Dawood, 2013; Khanam & Shamsuzzaman, 2015; Radadiya & Shah, 2015; Naik et al. 2015; Nevagi et al. 2015). In addition, substituted benzofurans find application such as fluorescent sensors, oxidant, antioxidants and brightening agents. The derivatives of 2,3-dihydro-benzofuranyl-3-acetic acid have been reported to be potent, selective and orally bioavailable G protein-coupled receptor 40 (GPR40) and free fatty acid receptor 1 agonists (FFA1) (Basanagouda et al., 2015). A perspective view of the molecule is shown in Fig. 1 and geomtric data for the intermolecular interactions are listed in Table 1.

Related literature top

For a related structures and background to benzofurans and their applications, see: Dawood (2013); Khanam & Shamsuzzaman (2015); Radadiya & Shah (2015); Naik et al. (2015); Nevagi et al. (2015). For the synthesis, see: Basanagouda et al. (2015).

Experimental top

6-Methoxy-4-bromomethylcoumarin (10 mM) was refluxed in 1 M NaOH (100 mL) for 2 h (monitored by TLC). The reaction mixture was cooled, neutralized with 1 M HCl and the obtained product was filtered off and dried. Colourless blocks were obtained by recrystallization from ethanol and ethyl acetate mixture by slow evaporation.

Structure description top

For a related structures and background to benzofurans and their applications, see: Dawood (2013); Khanam & Shamsuzzaman (2015); Radadiya & Shah (2015); Naik et al. (2015); Nevagi et al. (2015). For the synthesis, see: Basanagouda et al. (2015).

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) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top

Fig. 1. Molecular structure of the title compound showing atom labelling and 40% probability displacement ellipsoids.

2-(5-Methoxy-1-benzofuran-3-yl)acetic acid top

Crystal data top

C₁₁H₁₀O₄	D_x = 1.433 Mg m⁻³
M_r = 206.19	Melting point: 413 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.8096 (3) Å	Cell parameters from 5229 reflections
b = 13.2034 (5) Å	θ = 2.2–28.6°
c = 12.5738 (6) Å	µ = 0.11 mm⁻¹
β = 97.641 (3)°	T = 296 K
V = 955.93 (8) Å³	Block, colourless
Z = 4	0.35 × 0.30 × 0.25 mm
F(000) = 432

Data collection top

Bruker Kappa APEXII CCD diffractometer	2094 independent reflections
Radiation source: fine-focus sealed tube	1621 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and φ scan	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
T_min = 0.961, T_max = 0.979	k = −16→16
12813 measured reflections	l = −16→16

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0364P)² + 0.4069P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.110	(Δ/σ)_max < 0.001
S = 1.12	Δρ_max = 0.22 e Å⁻³
2094 reflections	Δρ_min = −0.16 e Å⁻³
137 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.017 (3)

Crystal data top

C₁₁H₁₀O₄	V = 955.93 (8) Å³
M_r = 206.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.8096 (3) Å	µ = 0.11 mm⁻¹
b = 13.2034 (5) Å	T = 296 K
c = 12.5738 (6) Å	0.35 × 0.30 × 0.25 mm
β = 97.641 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2094 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1621 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.979	R_int = 0.024
12813 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.12	Δρ_max = 0.22 e Å⁻³
2094 reflections	Δρ_min = −0.16 e Å⁻³
137 parameters

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	0.4010 (3)	0.61606 (13)	0.80077 (14)	0.0432 (4)
C2	0.2178 (3)	0.67578 (12)	0.82316 (13)	0.0389 (4)
H2	0.1770	0.6787	0.8922	0.047*
C3	0.0964 (3)	0.73116 (11)	0.74025 (12)	0.0349 (4)
C4	0.1631 (3)	0.72515 (13)	0.63818 (13)	0.0398 (4)
C5	0.3460 (3)	0.66724 (14)	0.61521 (14)	0.0477 (5)
H5	0.3882	0.6653	0.5464	0.057*
C6	0.4647 (3)	0.61208 (14)	0.69782 (15)	0.0479 (5)
H6	0.5890	0.5716	0.6848	0.057*
C7	0.7098 (4)	0.50545 (17)	0.8728 (2)	0.0646 (6)
H7A	0.7685	0.4733	0.9394	0.097*
H7B	0.6680	0.4547	0.8190	0.097*
H7C	0.8272	0.5488	0.8506	0.097*
C8	−0.0997 (3)	0.79821 (12)	0.73082 (13)	0.0378 (4)
C9	−0.1369 (3)	0.82596 (14)	0.62760 (14)	0.0476 (4)
H9	−0.2559	0.8692	0.5995	0.057*
C10	−0.2391 (3)	0.82719 (13)	0.81742 (14)	0.0421 (4)
H10A	−0.2708	0.7666	0.8566	0.051*
H10B	−0.3869	0.8541	0.7845	0.051*
C11	−0.1270 (3)	0.90353 (12)	0.89552 (13)	0.0367 (4)
O1	−0.2484 (2)	0.92135 (9)	0.97334 (10)	0.0491 (4)
H1	−0.1813	0.9636	1.0141	0.074*
O2	0.0578 (2)	0.94412 (10)	0.88700 (10)	0.0514 (4)
O3	0.5123 (3)	0.56354 (12)	0.88677 (12)	0.0665 (4)
O4	0.0193 (2)	0.78381 (10)	0.56745 (9)	0.0503 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0431 (9)	0.0419 (9)	0.0459 (10)	−0.0026 (7)	0.0101 (8)	−0.0053 (7)
C2	0.0428 (9)	0.0434 (9)	0.0328 (8)	−0.0051 (7)	0.0133 (7)	−0.0068 (7)
C3	0.0381 (8)	0.0356 (8)	0.0329 (8)	−0.0099 (7)	0.0113 (6)	−0.0089 (6)
C4	0.0456 (9)	0.0428 (9)	0.0325 (8)	−0.0113 (7)	0.0114 (7)	−0.0072 (7)
C5	0.0537 (11)	0.0543 (10)	0.0394 (9)	−0.0101 (9)	0.0218 (8)	−0.0140 (8)
C6	0.0464 (10)	0.0477 (10)	0.0535 (11)	−0.0024 (8)	0.0215 (8)	−0.0139 (8)
C7	0.0515 (12)	0.0578 (12)	0.0832 (15)	0.0092 (10)	0.0038 (11)	−0.0052 (11)
C8	0.0383 (9)	0.0399 (8)	0.0360 (8)	−0.0087 (7)	0.0075 (7)	−0.0069 (7)
C9	0.0477 (10)	0.0514 (10)	0.0439 (10)	−0.0038 (8)	0.0065 (8)	−0.0018 (8)
C10	0.0363 (9)	0.0472 (9)	0.0438 (9)	−0.0026 (7)	0.0093 (7)	−0.0071 (7)
C11	0.0408 (9)	0.0362 (8)	0.0349 (8)	0.0018 (7)	0.0118 (7)	−0.0002 (6)
O1	0.0558 (8)	0.0503 (7)	0.0461 (7)	−0.0115 (6)	0.0248 (6)	−0.0119 (6)
O2	0.0507 (8)	0.0599 (8)	0.0476 (7)	−0.0158 (6)	0.0207 (6)	−0.0172 (6)
O3	0.0661 (9)	0.0760 (10)	0.0590 (9)	0.0257 (8)	0.0144 (7)	0.0081 (7)
O4	0.0604 (8)	0.0598 (8)	0.0322 (6)	−0.0064 (6)	0.0114 (6)	−0.0009 (5)

Geometric parameters (Å, º) top

C1—O3	1.372 (2)	C7—H7A	0.9600
C1—C2	1.383 (2)	C7—H7B	0.9600
C1—C6	1.394 (2)	C7—H7C	0.9600
C2—C3	1.387 (2)	C8—C9	1.338 (2)
C2—H2	0.9300	C8—C10	1.491 (2)
C3—C4	1.391 (2)	C9—O4	1.374 (2)
C3—C8	1.435 (2)	C9—H9	0.9300
C4—C5	1.371 (2)	C10—C11	1.495 (2)
C4—O4	1.375 (2)	C10—H10A	0.9700
C5—C6	1.377 (3)	C10—H10B	0.9700
C5—H5	0.9300	C11—O2	1.217 (2)
C6—H6	0.9300	C11—O1	1.3014 (18)
C7—O3	1.410 (2)	O1—H1	0.8200

O3—C1—C2	115.00 (15)	O3—C7—H7C	109.5
O3—C1—C6	123.86 (17)	H7A—C7—H7C	109.5
C2—C1—C6	121.13 (17)	H7B—C7—H7C	109.5
C1—C2—C3	118.41 (15)	C9—C8—C3	105.85 (15)
C1—C2—H2	120.8	C9—C8—C10	127.22 (17)
C3—C2—H2	120.8	C3—C8—C10	126.89 (15)
C2—C3—C4	119.14 (15)	C8—C9—O4	112.94 (17)
C2—C3—C8	134.93 (14)	C8—C9—H9	123.5
C4—C3—C8	105.92 (15)	O4—C9—H9	123.5
C5—C4—O4	126.81 (15)	C8—C10—C11	114.92 (14)
C5—C4—C3	123.03 (17)	C8—C10—H10A	108.5
O4—C4—C3	110.16 (15)	C11—C10—H10A	108.5
C4—C5—C6	117.44 (15)	C8—C10—H10B	108.5
C4—C5—H5	121.3	C11—C10—H10B	108.5
C6—C5—H5	121.3	H10A—C10—H10B	107.5
C5—C6—C1	120.83 (17)	O2—C11—O1	123.98 (15)
C5—C6—H6	119.6	O2—C11—C10	123.47 (14)
C1—C6—H6	119.6	O1—C11—C10	112.55 (14)
O3—C7—H7A	109.5	C11—O1—H1	109.5
O3—C7—H7B	109.5	C1—O3—C7	118.88 (16)
H7A—C7—H7B	109.5	C9—O4—C4	105.13 (13)

O3—C1—C2—C3	−179.94 (15)	C4—C3—C8—C9	0.53 (18)
C6—C1—C2—C3	0.7 (3)	C2—C3—C8—C10	−1.0 (3)
C1—C2—C3—C4	−0.3 (2)	C4—C3—C8—C10	178.12 (15)
C1—C2—C3—C8	178.71 (17)	C3—C8—C9—O4	−0.6 (2)
C2—C3—C4—C5	−0.5 (2)	C10—C8—C9—O4	−178.15 (15)
C8—C3—C4—C5	−179.78 (15)	C9—C8—C10—C11	−105.9 (2)
C2—C3—C4—O4	178.93 (14)	C3—C8—C10—C11	77.0 (2)
C8—C3—C4—O4	−0.33 (17)	C8—C10—C11—O2	4.0 (3)
O4—C4—C5—C6	−178.48 (16)	C8—C10—C11—O1	−175.80 (15)
C3—C4—C5—C6	0.9 (3)	C2—C1—O3—C7	−176.25 (17)
C4—C5—C6—C1	−0.4 (3)	C6—C1—O3—C7	3.1 (3)
O3—C1—C6—C5	−179.65 (17)	C8—C9—O4—C4	0.38 (19)
C2—C1—C6—C5	−0.3 (3)	C5—C4—O4—C9	179.42 (17)
C2—C3—C8—C9	−178.54 (18)	C3—C4—O4—C9	−0.01 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.82	2.6357 (17)	174
C2—H2···O4ⁱⁱ	0.93	2.55	3.4629 (19)	169

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.82	2.6357 (17)	174
C2—H2···O4ⁱⁱ	0.93	2.55	3.4629 (19)	169

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

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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