4-(8-Hydr­oxy-3-methyl-1,4-dioxo-1,4-dihydro-2-naphth­yl)butanoic acid

Wang, Y.-F.; Tang, H.; Liu, Y.-C.; Chen, Z.-F.; Liang, H.

doi:10.1107/S1600536809040021

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2737

https://doi.org/10.1107/S1600536809040021

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4-(8-Hydroxy-3-methyl-1,4-dioxo-1,4-dihydro-2-naphthyl)butanoic acid

Yan-Fei Wang,^a Huang Tang,^b Yan-Cheng Liu,^b Zhen-Feng Chen ^b ^* and Hong Liang ^b

^aSchool of Chemistry and Chemical Engineering, Central South University, Changsha 410083, People's Republic of China, and ^bKey Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education), Guangxi Normal University, Guilin 541004, People's Republic of China
^*Correspondence e-mail: chenzfgxnu@yahoo.com

(Received 11 September 2009; accepted 1 October 2009; online 17 October 2009)

In the title compound, C₁₅H₁₄O₅, 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_r = 274.26
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.073
wR(F²) = 0.198
S = 1.09
2405 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z+2.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040021/pk2192Isup2.hkl

checkCIF report

Comment top

Plumbagin is a potent toxic natural product extracted from Plumbago Zeylanica L. (Plumbaginaceae), which has been used in China as well as other Asian countries for the treatment of rheumatoid arthritis, dysmenorrhea, injury by bumping, and even cancer. The title compound is a 2-substituted 1,4-naphthoquinone derivative. Its synthesis has been reported by Salmon-Chemin et al.(2001), we now report its structure. The molecular structure of the title compound is shown in Fig.1. The bond lengths and angles of the napthoquinone molecule are normal and comparable to those of plumbagin (Ghouse & Rao, 1974; Vijayalakshmi, et al., 1987). Geometric parameters for the butanoic acid group are also normal. As shown in Fig.2, a two-dimensional network is generated via intermolecular hydrogen bond interactions involving C—H···O, O—H···O.

Related literature top

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 top

0.2 mmol compound were dissolved in 10 ml methanol and 10 ml CH₂Cl₂. The resulting red solution was filtered. The filtrate was allowed to sit under ambient conditions for two weeks, dark-red block crystals were obtained.

Structure description top

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).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing of molecules roughly down the [100] direction showing the two-dimensional network of molecules. Hydrogen bonds are shown as dashed lines.

4-(8-Hydroxy-3-methyl-1,4-dioxo-1,4-dihydro-2-naphthyl)butanoic acid top

Crystal data top

C₁₅H₁₄O₅	F(000) = 576
M_r = 274.26	D_x = 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

Data collection top

Rigaku Mercury CCD diffractometer	2405 independent reflections
Radiation source: fine-focus sealed tube	1779 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.4°, θ_min = 3.4°
ω scans	h = −13→13
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	k = −11→12
T_min = 0.734, T_max = 0.975	l = −13→15
11416 measured 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.198	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0888P)² + 0.5298P] where P = (F_o² + 2F_c²)/3
2405 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₄O₅	V = 1319.0 (6) Å³
M_r = 274.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.881 (3) Å	µ = 0.10 mm⁻¹
b = 9.973 (2) Å	T = 293 K
c = 12.705 (3) Å	0.45 × 0.30 × 0.24 mm
β = 106.936 (5)°

Data collection top

Rigaku Mercury CCD diffractometer	2405 independent reflections
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	1779 reflections with I > 2σ(I)
T_min = 0.734, T_max = 0.975	R_int = 0.038
11416 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.198	H-atom parameters constrained
S = 1.09	Δρ_max = 0.19 e Å⁻³
2405 reflections	Δρ_min = −0.25 e Å⁻³
184 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₅
M_r	274.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.881 (3), 9.973 (2), 12.705 (3)
β (°)	106.936 (5)
V (Å³)	1319.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.30 × 0.24

Data collection
Diffractometer	Rigaku Mercury CCD
Absorption correction	Multi-scan (REQAB: Jacobson, 1998)
T_min, T_max	0.734, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	11416, 2405, 1779
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.198, 1.09
No. of reflections	2405
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.25

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku/MSC & Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.43	3.315 (4)	160.1
O5—H5···O4ⁱⁱ	0.82	1.77	2.589 (3)	174.0
O1—H1···O3	0.82	1.87	2.582 (3)	145.2

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (No. 20861002), the 973 Plan of China (2009CB526503) and the Natural Science Foundation of Guangxi Province of China (Nos. 0429001, 0991012Z, 0991003), and the Open Foundation of the Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China) for financial support.

References

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