2-(2-Methyl-naphtho[2,1-b]furan-1-yl)acetic acid.

In the title mol-ecule, C(15)H(12)O(3), the two six-membered and one five-membered fused-ring system is almost planar and the CH(2)C(=O)OH residue is essentially orthogonal to it. In the crystal structure, centrosymmetric dimers are formed via the carboxylic acid {⋯O=C-O-H}(2) synthon.

Related literature

For related literature, see: Haselgrove et al. (1999 ▶); Jevric et al. (2001 ▶).

Experimental

Crystal data

C15H12O3

M = 240.25

Monoclinic,

a = 31.380 (3) Å

b = 4.8370 (4) Å

c = 15.7885 (13) Å

β = 98.087 (2)°

V = 2372.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 223 (2) K

0.49 × 0.36 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

9334 measured reflections

3445 independent reflections

2790 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.138

S = 1.04

3445 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT and SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015572/lh2631sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015572/lh2631Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12O3	F000 = 1008
Mr = 240.25	Dx = 1.345 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 3301 reflections
a = 31.380 (3) Å	θ = 2.6–29.4º
b = 4.8370 (4) Å	µ = 0.09 mm−1
c = 15.7885 (13) Å	T = 223 (2) K
β = 98.087 (2)º	Block, colourless
V = 2372.6 (3) Å3	0.49 × 0.36 × 0.18 mm
Z = 8

Bruker SMART CCD diffractometer	2790 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Monochromator: graphite	θmax = 30.0º
T = 223(2) K	θmin = 2.6º
ω scans	h = −43→43
Absorption correction: none	k = −6→4
9334 measured reflections	l = −22→22
3445 independent reflections

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0801P)2 + 0.5375P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3445 reflections	Δρmax = 0.34 e Å−3
164 parameters	Δρmin = −0.15 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

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 > σ(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
O3	0.39156 (3)	0.5681 (2)	0.14890 (5)	0.0436 (2)
O11	0.47261 (3)	0.47260 (18)	0.40193 (6)	0.0458 (2)
O12	0.46215 (3)	0.7752 (2)	0.50211 (6)	0.0597 (3)
H12	0.4808	0.6801	0.5312	0.090*
C1	0.40206 (3)	0.6881 (2)	0.28846 (7)	0.0322 (2)
C2	0.41414 (4)	0.7340 (3)	0.21078 (7)	0.0389 (3)
C3a	0.36422 (4)	0.4133 (2)	0.19008 (7)	0.0371 (3)
C4	0.33570 (4)	0.2173 (3)	0.14967 (8)	0.0445 (3)
H4	0.3340	0.1805	0.0908	0.053*
C5	0.31044 (4)	0.0821 (3)	0.19964 (8)	0.0447 (3)
H5	0.2911	−0.0532	0.1748	0.054*
C5a	0.31254 (3)	0.1401 (2)	0.28866 (8)	0.0374 (3)
C6	0.28513 (4)	0.0037 (3)	0.33887 (10)	0.0480 (3)
H6	0.2655	−0.1288	0.3131	0.058*
C7	0.28646 (4)	0.0600 (3)	0.42402 (10)	0.0511 (3)
H7	0.2675	−0.0308	0.4559	0.061*
C8	0.31603 (4)	0.2532 (3)	0.46375 (8)	0.0451 (3)
H8	0.3170	0.2900	0.5225	0.054*
C9	0.34350 (4)	0.3890 (2)	0.41782 (7)	0.0360 (2)
H9	0.3634	0.5163	0.4456	0.043*
C9a	0.34237 (3)	0.3400 (2)	0.32913 (7)	0.0312 (2)
C9b	0.36901 (3)	0.4774 (2)	0.27625 (7)	0.0309 (2)
C11	0.42022 (3)	0.8343 (2)	0.36877 (7)	0.0336 (2)
H11A	0.3967	0.8781	0.4012	0.040*
H11B	0.4329	1.0095	0.3535	0.040*
C12	0.45400 (3)	0.6725 (2)	0.42568 (6)	0.0306 (2)
C21	0.44569 (4)	0.9241 (4)	0.17989 (10)	0.0560 (4)
H21A	0.4541	1.0645	0.2229	0.084*
H21B	0.4327	1.0118	0.1273	0.084*
H21C	0.4709	0.8204	0.1693	0.084*

	U11	U22	U33	U12	U13	U23
O3	0.0459 (5)	0.0549 (5)	0.0297 (4)	0.0104 (4)	0.0047 (3)	0.0020 (3)
O11	0.0497 (5)	0.0434 (5)	0.0394 (5)	0.0167 (4)	−0.0108 (4)	−0.0094 (3)
O12	0.0662 (6)	0.0695 (7)	0.0373 (5)	0.0348 (5)	−0.0140 (4)	−0.0176 (4)
C1	0.0310 (5)	0.0332 (5)	0.0311 (5)	0.0067 (4)	0.0001 (4)	0.0038 (4)
C2	0.0352 (5)	0.0463 (6)	0.0347 (5)	0.0086 (4)	0.0029 (4)	0.0069 (5)
C3a	0.0392 (5)	0.0411 (6)	0.0293 (5)	0.0108 (4)	−0.0013 (4)	−0.0013 (4)
C4	0.0490 (6)	0.0471 (7)	0.0334 (6)	0.0121 (5)	−0.0089 (5)	−0.0100 (5)
C5	0.0424 (6)	0.0386 (6)	0.0476 (7)	0.0056 (5)	−0.0129 (5)	−0.0106 (5)
C5a	0.0329 (5)	0.0316 (5)	0.0447 (6)	0.0052 (4)	−0.0055 (4)	−0.0004 (4)
C6	0.0395 (6)	0.0379 (6)	0.0636 (8)	−0.0032 (5)	−0.0037 (5)	0.0045 (6)
C7	0.0460 (7)	0.0459 (7)	0.0624 (9)	−0.0033 (5)	0.0110 (6)	0.0150 (6)
C8	0.0519 (7)	0.0433 (6)	0.0407 (6)	0.0039 (5)	0.0087 (5)	0.0085 (5)
C9	0.0405 (5)	0.0331 (5)	0.0335 (5)	0.0031 (4)	0.0019 (4)	0.0016 (4)
C9a	0.0312 (5)	0.0281 (5)	0.0325 (5)	0.0070 (4)	−0.0016 (4)	0.0004 (4)
C9b	0.0318 (5)	0.0306 (5)	0.0284 (5)	0.0075 (4)	−0.0017 (4)	−0.0010 (4)
C11	0.0338 (5)	0.0294 (5)	0.0357 (5)	0.0029 (4)	−0.0013 (4)	0.0016 (4)
C12	0.0289 (4)	0.0312 (5)	0.0305 (5)	−0.0006 (4)	0.0005 (3)	−0.0001 (4)
C21	0.0455 (7)	0.0702 (10)	0.0545 (8)	0.0040 (6)	0.0150 (6)	0.0185 (7)

O3—C3a	1.3697 (15)	C5a—C9a	1.4323 (15)
O3—C2	1.3807 (15)	C6—C7	1.366 (2)
O11—C12	1.2157 (13)	C6—H6	0.9400
O12—C12	1.2968 (13)	C7—C8	1.401 (2)
O12—H12	0.8300	C7—H7	0.9400
C1—C2	1.3519 (16)	C8—C9	1.3697 (17)
C1—C9b	1.4474 (15)	C8—H8	0.9400
C1—C11	1.4930 (15)	C9—C9a	1.4157 (15)
C2—C21	1.4832 (18)	C9—H9	0.9400
C3a—C9b	1.3829 (15)	C9a—C9b	1.4261 (15)
C3a—C4	1.3950 (17)	C11—C12	1.5084 (14)
C4—C5	1.362 (2)	C11—H11A	0.9800
C4—H4	0.9400	C11—H11B	0.9800
C5—C5a	1.4255 (18)	C21—H21A	0.9700
C5—H5	0.9400	C21—H21B	0.9700
C5a—C6	1.4127 (18)	C21—H21C	0.9700
C3a—O3—C2	105.97 (9)	C9—C8—H8	119.7
C12—O12—H12	109.5	C7—C8—H8	119.7
C2—C1—C9b	106.37 (10)	C8—C9—C9a	120.89 (11)
C2—C1—C11	124.78 (11)	C8—C9—H9	119.6
C9b—C1—C11	128.84 (10)	C9a—C9—H9	119.6
C1—C2—O3	111.41 (11)	C9—C9a—C9b	124.47 (10)
C1—C2—C21	133.27 (12)	C9—C9a—C5a	118.55 (11)
O3—C2—C21	115.32 (11)	C9b—C9a—C5a	116.98 (10)
O3—C3a—C9b	110.84 (10)	C3a—C9b—C9a	118.67 (10)
O3—C3a—C4	123.97 (10)	C3a—C9b—C1	105.40 (10)
C9b—C3a—C4	125.19 (11)	C9a—C9b—C1	135.91 (9)
C5—C4—C3a	116.72 (11)	C1—C11—C12	114.36 (9)
C5—C4—H4	121.6	C1—C11—H11A	108.7
C3a—C4—H4	121.6	C12—C11—H11A	108.7
C4—C5—C5a	121.79 (11)	C1—C11—H11B	108.7
C4—C5—H5	119.1	C12—C11—H11B	108.7
C5a—C5—H5	119.1	H11A—C11—H11B	107.6
C6—C5a—C5	120.93 (11)	O11—C12—O12	123.46 (9)
C6—C5a—C9a	118.45 (11)	O11—C12—C11	123.82 (9)
C5—C5a—C9a	120.62 (11)	O12—C12—C11	112.68 (9)
C7—C6—C5a	121.48 (12)	C2—C21—H21A	109.5
C7—C6—H6	119.3	C2—C21—H21B	109.5
C5a—C6—H6	119.3	H21A—C21—H21B	109.5
C6—C7—C8	120.00 (12)	C2—C21—H21C	109.5
C6—C7—H7	120.0	H21A—C21—H21C	109.5
C8—C7—H7	120.0	H21B—C21—H21C	109.5
C9—C8—C7	120.60 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O11i	0.83	1.83	2.6553 (14)	170
C21—H21B···O12ii	0.97	2.52	3.2663 (19)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12⋯O11i	0.83	1.83	2.6553 (14)	170
C21—H21B⋯O12ii	0.97	2.52	3.2663 (19)	134

Symmetry codes: (i) ; (ii) .