4-(8-Hydr-oxy-3-methyl-1,4-dioxo-1,4-dihydro-2-naphth-yl)butanoic acid.

In the title compound, C(15)H(14)O(5), an intramolecular O-H⋯O hydrogen bond occurs. In the crystal, the molecules form inversion dimers linked by pairs of O-H⋯O bonds, which are further linked by C-H⋯O interactions.

Related literature

For the synthesis and biological properties of the title compound, see: Salmon-Chemin et al. (2001 ▶). For crystal structures of similar compounds, see: Vijayalakshmi et al. (1987 ▶); Ghouse & Rao (1974 ▶).

Experimental

Crystal data

C15H14O5

M = 274.26

Monoclinic,

a = 10.881 (3) Å

b = 9.973 (2) Å

c = 12.705 (3) Å

β = 106.936 (5)°

V = 1319.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.45 × 0.30 × 0.24 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB: Jacobson, 1998 ▶) T min = 0.734, T max = 0.975

11416 measured reflections

2405 independent reflections

1779 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.198

S = 1.09

2405 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040021/pk2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040021/pk2192Isup2.hkl

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

C15H14O5	F(000) = 576
Mr = 274.26	Dx = 1.381 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 3725 reflections
a = 10.881 (3) Å	θ = 3.4–25.3°
b = 9.973 (2) Å	µ = 0.10 mm−1
c = 12.705 (3) Å	T = 293 K
β = 106.936 (5)°	Block, dark-red
V = 1319.0 (6) Å3	0.45 × 0.30 × 0.24 mm
Z = 4

Rigaku Mercury CCD diffractometer	2405 independent reflections
Radiation source: fine-focus sealed tube	1779 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 7.31 pixels mm-1	θmax = 25.4°, θmin = 3.4°
ω scans	h = −13→13
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	k = −11→12
Tmin = 0.734, Tmax = 0.975	l = −13→15
11416 measured reflections

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0888P)2 + 0.5298P] where P = (Fo2 + 2Fc2)/3
2405 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.25 e Å−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.

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
O1	0.9902 (2)	0.8451 (2)	0.6287 (2)	0.0868 (8)
H1	1.0115	0.8001	0.6851	0.130*
O2	0.7285 (3)	0.3526 (3)	0.4035 (2)	0.0943 (9)
O3	1.0036 (2)	0.6313 (2)	0.74605 (17)	0.0752 (7)
O4	0.9090 (2)	0.1025 (2)	0.90860 (19)	0.0749 (7)
O5	1.0253 (3)	0.1478 (2)	1.08016 (19)	0.0808 (8)
H5	1.0411	0.0674	1.0806	0.121*
C1	0.9241 (3)	0.7683 (3)	0.5446 (3)	0.0619 (8)
C2	0.8795 (3)	0.8269 (4)	0.4409 (3)	0.0741 (10)
H2	0.8964	0.9169	0.4317	0.089*
C3	0.8115 (3)	0.7538 (4)	0.3534 (3)	0.0782 (11)
H3	0.7836	0.7940	0.2846	0.094*
C4	0.7827 (3)	0.6200 (4)	0.3646 (2)	0.0665 (9)
H4	0.7346	0.5716	0.3040	0.080*
C5	0.8260 (2)	0.5593 (3)	0.4661 (2)	0.0516 (7)
C6	0.7964 (3)	0.4165 (3)	0.4808 (2)	0.0587 (8)
C7	0.8472 (3)	0.3520 (3)	0.5893 (2)	0.0523 (7)
C8	0.9164 (2)	0.4235 (3)	0.6766 (2)	0.0475 (7)
C9	0.9428 (3)	0.5675 (3)	0.6644 (2)	0.0490 (7)
C10	0.8974 (2)	0.6322 (3)	0.5572 (2)	0.0480 (7)
C11	0.8153 (3)	0.2063 (3)	0.5962 (3)	0.0781 (10)
H11A	0.8895	0.1597	0.6407	0.117*
H11B	0.7897	0.1682	0.5237	0.117*
H11C	0.7462	0.1978	0.6287	0.117*
C12	0.9674 (3)	0.3671 (3)	0.7905 (2)	0.0565 (8)
H12A	1.0433	0.4168	0.8303	0.068*
H12B	0.9923	0.2744	0.7859	0.068*
C13	0.8682 (3)	0.3741 (3)	0.8535 (2)	0.0593 (8)
H13A	0.8385	0.4658	0.8531	0.071*
H13B	0.7949	0.3189	0.8165	0.071*
C14	0.9219 (3)	0.3269 (3)	0.9717 (3)	0.0640 (8)
H14A	0.9995	0.3771	1.0063	0.077*
H14B	0.8600	0.3470	1.0111	0.077*
C15	0.9521 (3)	0.1824 (3)	0.9828 (3)	0.0582 (8)

	U11	U22	U33	U12	U13	U23
O1	0.1058 (19)	0.0542 (14)	0.0918 (18)	−0.0175 (13)	0.0155 (15)	0.0019 (12)
O2	0.1062 (19)	0.106 (2)	0.0626 (15)	−0.0342 (16)	0.0118 (14)	−0.0271 (14)
O3	0.0995 (17)	0.0634 (13)	0.0507 (12)	−0.0164 (12)	0.0031 (12)	−0.0043 (10)
O4	0.0928 (17)	0.0626 (14)	0.0654 (15)	0.0010 (12)	0.0167 (13)	0.0090 (11)
O5	0.1021 (18)	0.0667 (15)	0.0655 (15)	0.0022 (14)	0.0119 (13)	0.0084 (11)
C1	0.0604 (17)	0.0583 (19)	0.067 (2)	0.0009 (15)	0.0189 (16)	0.0156 (16)
C2	0.074 (2)	0.065 (2)	0.087 (3)	0.0133 (17)	0.030 (2)	0.0290 (19)
C3	0.069 (2)	0.106 (3)	0.064 (2)	0.024 (2)	0.0276 (18)	0.040 (2)
C4	0.0576 (18)	0.097 (3)	0.0443 (16)	0.0080 (17)	0.0132 (14)	0.0075 (16)
C5	0.0471 (15)	0.0657 (19)	0.0428 (15)	0.0011 (13)	0.0143 (13)	0.0042 (13)
C6	0.0525 (16)	0.073 (2)	0.0518 (17)	−0.0070 (15)	0.0166 (14)	−0.0131 (15)
C7	0.0511 (15)	0.0492 (16)	0.0593 (17)	−0.0005 (13)	0.0204 (14)	−0.0020 (13)
C8	0.0454 (14)	0.0504 (16)	0.0496 (15)	0.0017 (12)	0.0183 (12)	0.0047 (12)
C9	0.0519 (15)	0.0507 (16)	0.0427 (15)	−0.0022 (13)	0.0110 (13)	0.0008 (12)
C10	0.0479 (15)	0.0533 (16)	0.0429 (15)	0.0017 (12)	0.0134 (12)	0.0071 (12)
C11	0.079 (2)	0.0543 (19)	0.104 (3)	−0.0133 (17)	0.031 (2)	−0.0053 (18)
C12	0.0590 (17)	0.0578 (18)	0.0545 (17)	0.0092 (14)	0.0195 (14)	0.0184 (13)
C13	0.0690 (19)	0.0570 (18)	0.0561 (17)	0.0093 (14)	0.0247 (15)	0.0090 (14)
C14	0.080 (2)	0.060 (2)	0.0567 (18)	0.0069 (16)	0.0276 (16)	0.0067 (14)
C15	0.0665 (18)	0.062 (2)	0.0472 (16)	−0.0049 (15)	0.0177 (14)	0.0079 (14)

O1—C1	1.341 (4)	C7—C8	1.349 (4)
O1—H1	0.8200	C7—C11	1.502 (4)
O2—C6	1.222 (3)	C8—C9	1.482 (4)
O3—C9	1.232 (3)	C8—C12	1.500 (4)
O4—C15	1.220 (4)	C9—C10	1.457 (4)
O5—C15	1.307 (4)	C11—H11A	0.9600
O5—H5	0.8200	C11—H11B	0.9600
C1—C2	1.393 (4)	C11—H11C	0.9600
C1—C10	1.407 (4)	C12—C13	1.521 (4)
C2—C3	1.355 (5)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.387 (5)	C13—C14	1.520 (4)
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.377 (4)	C13—H13B	0.9700
C4—H4	0.9300	C14—C15	1.476 (4)
C5—C10	1.395 (4)	C14—H14A	0.9700
C5—C6	1.484 (4)	C14—H14B	0.9700
C6—C7	1.475 (4)
C1—O1—H1	109.5	C5—C10—C9	120.0 (3)
C15—O5—H5	109.5	C1—C10—C9	120.5 (3)
O1—C1—C2	118.1 (3)	C7—C11—H11A	109.5
O1—C1—C10	122.8 (3)	C7—C11—H11B	109.5
C2—C1—C10	119.1 (3)	H11A—C11—H11B	109.5
C3—C2—C1	120.4 (3)	C7—C11—H11C	109.5
C3—C2—H2	119.8	H11A—C11—H11C	109.5
C1—C2—H2	119.8	H11B—C11—H11C	109.5
C2—C3—C4	121.3 (3)	C8—C12—C13	111.8 (2)
C2—C3—H3	119.3	C8—C12—H12A	109.3
C4—C3—H3	119.3	C13—C12—H12A	109.3
C5—C4—C3	119.5 (3)	C8—C12—H12B	109.3
C5—C4—H4	120.3	C13—C12—H12B	109.3
C3—C4—H4	120.3	H12A—C12—H12B	107.9
C4—C5—C10	120.2 (3)	C14—C13—C12	112.2 (2)
C4—C5—C6	120.8 (3)	C14—C13—H13A	109.2
C10—C5—C6	119.0 (2)	C12—C13—H13A	109.2
O2—C6—C7	119.9 (3)	C14—C13—H13B	109.2
O2—C6—C5	120.1 (3)	C12—C13—H13B	109.2
C7—C6—C5	120.0 (2)	H13A—C13—H13B	107.9
C8—C7—C6	120.4 (3)	C15—C14—C13	114.1 (3)
C8—C7—C11	123.1 (3)	C15—C14—H14A	108.7
C6—C7—C11	116.5 (3)	C13—C14—H14A	108.7
C7—C8—C9	120.3 (2)	C15—C14—H14B	108.7
C7—C8—C12	123.8 (3)	C13—C14—H14B	108.7
C9—C8—C12	115.9 (2)	H14A—C14—H14B	107.6
O3—C9—C10	120.8 (3)	O4—C15—O5	123.4 (3)
O3—C9—C8	119.0 (2)	O4—C15—C14	122.6 (3)
C10—C9—C8	120.2 (2)	O5—C15—C14	113.9 (3)
C5—C10—C1	119.4 (3)
O1—C1—C2—C3	−179.5 (3)	C7—C8—C9—C10	−1.9 (4)
C10—C1—C2—C3	−0.1 (5)	C12—C8—C9—C10	−180.0 (2)
C1—C2—C3—C4	1.0 (5)	C4—C5—C10—C1	0.3 (4)
C2—C3—C4—C5	−1.2 (5)	C6—C5—C10—C1	−178.9 (3)
C3—C4—C5—C10	0.5 (4)	C4—C5—C10—C9	179.9 (3)
C3—C4—C5—C6	179.7 (3)	C6—C5—C10—C9	0.7 (4)
C4—C5—C6—O2	−3.0 (4)	O1—C1—C10—C5	178.8 (3)
C10—C5—C6—O2	176.2 (3)	C2—C1—C10—C5	−0.5 (4)
C4—C5—C6—C7	178.0 (3)	O1—C1—C10—C9	−0.7 (4)
C10—C5—C6—C7	−2.8 (4)	C2—C1—C10—C9	179.9 (3)
O2—C6—C7—C8	−176.4 (3)	O3—C9—C10—C5	−178.5 (3)
C5—C6—C7—C8	2.6 (4)	C8—C9—C10—C5	1.7 (4)
O2—C6—C7—C11	2.5 (4)	O3—C9—C10—C1	1.0 (4)
C5—C6—C7—C11	−178.5 (3)	C8—C9—C10—C1	−178.8 (3)
C6—C7—C8—C9	−0.2 (4)	C7—C8—C12—C13	−85.5 (3)
C11—C7—C8—C9	−179.1 (3)	C9—C8—C12—C13	92.5 (3)
C6—C7—C8—C12	177.7 (2)	C8—C12—C13—C14	−175.7 (2)
C11—C7—C8—C12	−1.1 (4)	C12—C13—C14—C15	−67.6 (4)
C7—C8—C9—O3	178.3 (3)	C13—C14—C15—O4	−17.6 (5)
C12—C8—C9—O3	0.2 (4)	C13—C14—C15—O5	164.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.43	3.315 (4)	160
O5—H5···O4ii	0.82	1.77	2.589 (3)	174
O1—H1···O3	0.82	1.87	2.582 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.43	3.315 (4)	160
O5—H5⋯O4ii	0.82	1.77	2.589 (3)	174
O1—H1⋯O3	0.82	1.87	2.582 (3)	145

Symmetry codes: (i) ; (ii) .