Crystal structure of 2-(5-meth-oxy-1-benzo-furan-3-yl)acetic acid.

The benzo-furan 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 meth-oxy 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 mol-ecules are linked by O-H⋯O hydrogen bonds to form eight-membered {⋯HOCO}2 synthons. The dimeric aggregates assemble into supra-molecular layers in the ab plane via benzene-C-H⋯O(ring) inter-actions.

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 ▸).

Experimental

Crystal data

C11H10O4

M = 206.19

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.12

2094 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.16 e Å−3

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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015023609/tk5414sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023609/tk5414Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015023609/tk5414Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015023609/tk5414fig1.tif

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

CCDC reference: 1401314

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H10O4	Dx = 1.433 Mg m−3
Mr = 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

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

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(Fo2) + (0.0364P)2 + 0.4069P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 0.22 e Å−3
2094 reflections	Δρmin = −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)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .