2-[Hy­droxy(4-meth­oxy­phen­yl)methyl­idene]indane-1,3-dione

Gu, J.-C.; Zhu, B.-X.; Zhang, Y.-Q.

doi:10.1107/S1600536812021824

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1907

doi:10.1107/S1600536812021824

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2-[Hydroxy(4-methoxyphenyl)methylidene]indane-1,3-dione

Jing-Chi Gu,^a Bi-Xue Zhu ^a ^* and Yun-Qian Zhang ^a

^aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China.
^*Correspondence e-mail: gzubxzhu@126.com

(Received 23 April 2012; accepted 14 May 2012; online 26 May 2012)

In the title compound, C₁₇H₁₂O₄, there is an intramolecular O—H⋯O hydrogen bond. The dihedral angle between the indane ring system [maximun deviation = 0.023 (2) Å] and the benzene ring is 37.42 (9)°.

Related literature

For general background to the synthesis and pharmacological properties of 1,3-indandione derivatives, see: Cheng et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₂O₄
M_r = 280.27
Monoclinic, P 2₁ /n
a = 17.779 (4) Å
b = 3.8405 (9) Å
c = 19.026 (4) Å
β = 92.984 (8)°
V = 1297.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.23 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.977, T_max = 0.982
10521 measured reflections
2311 independent reflections
1553 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.127
S = 0.97
2311 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.78	2.539 (2)	152

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021824/nc2275sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021824/nc2275Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021824/nc2275Isup3.cml

checkCIF report

Comment top

In general, 1,3-indandione derivatives demonstrate an anticoagulant properties. The synthesis and pharmacological properties of some chemicals of this category have been reported (Dolmella et al., 1961). The prepare of derivatives containing 2H-indene-1,3-dione unit have received very substantial attention (Cheng et al., 2011). In view of this biological importance a part of our ongoing studies of 1,3-indandione derivatives includes the crystal structure determination of the title compound. The molecule of the title compound shows non-coplanar structure (Fig. 1). An intramolecular O—H···O hydrogen bonds is observed (Table 1), which links the hydroxyl oxygen to the nearby keto-oxygen atom of the 2H-indene-1,3-dione unit, forming a planar six-membered ring. The dihedral angle between the six-membered ring and the plane of 2H-indene-1,3-dione unit is 173.94°, and the dihedral angle between the six-membered ring and the benzene ring is 148.51°.

Related literature top

For general background to the synthesis and pharmacological properties of 1,3-indandione derivatives, see: Dolmella et al. (1961); Cheng et al. (2011).

Experimental top

p-methoxy-acetophenone (166 mg, 1.2 mmol) in tetrahydrofuran (15 ml) was added slowly with stirring to dimethyl phthalate(232.8 mg, 1.2 mmol) and NaH (120 mg, 5 mmol) in THF (30 ml) and the mixture was heated at reflux for 12 h. The solution was allowed to cool and the THF was removed partly under reduced pressure. The precipitate was collected by filtration and washed with waterand dried; the residue was crystallized from CHCl₃ to afford the title compound as a yellow solid [yield 65%, m.p. 398–400 K]. Single crystal suitable for X-ray diffraction was prepared by slow evaporation of a solution of the title compound in methanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

2-[Hydroxy(4-methoxyphenyl)methylidene]indane-1,3-dione top

Crystal data top

C₁₇H₁₂O₄	F(000) = 584
M_r = 280.27	D_x = 1.435 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2311 reflections
a = 17.779 (4) Å	θ = 1.5–25.1°
b = 3.8405 (9) Å	µ = 0.10 mm⁻¹
c = 19.026 (4) Å	T = 293 K
β = 92.984 (8)°	Block, colorless
V = 1297.4 (5) Å³	0.23 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2311 independent reflections
Radiation source: fine-focus sealed tube	1553 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scan	θ_max = 25.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→19
T_min = 0.977, T_max = 0.982	k = −4→4
10521 measured reflections	l = −22→22

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0678P)²] where P = (F_o² + 2F_c²)/3
2311 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₂O₄	V = 1297.4 (5) Å³
M_r = 280.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.779 (4) Å	µ = 0.10 mm⁻¹
b = 3.8405 (9) Å	T = 293 K
c = 19.026 (4) Å	0.23 × 0.19 × 0.18 mm
β = 92.984 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2311 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1553 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.982	R_int = 0.077
10521 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 0.97	Δρ_max = 0.21 e Å⁻³
2311 reflections	Δρ_min = −0.17 e Å⁻³
191 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.

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 > 2sigma(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
C1	0.51739 (13)	0.1113 (6)	0.36369 (11)	0.0431 (6)
C2	0.44114 (13)	0.2488 (6)	0.37373 (11)	0.0407 (6)
C3	0.40844 (16)	0.3680 (6)	0.43398 (12)	0.0551 (7)
H3	0.4347	0.3647	0.4775	0.066*
C4	0.33527 (16)	0.4919 (7)	0.42678 (14)	0.0561 (7)
H4	0.3119	0.5734	0.4662	0.067*
C5	0.29666 (15)	0.4961 (6)	0.36209 (13)	0.0513 (7)
H5	0.2477	0.5817	0.3587	0.062*
C6	0.32898 (13)	0.3762 (6)	0.30215 (12)	0.0448 (6)
H6	0.3026	0.3810	0.2586	0.054*
C7	0.40147 (12)	0.2492 (5)	0.30887 (10)	0.0370 (5)
C8	0.44965 (13)	0.1018 (5)	0.25401 (11)	0.0366 (5)
C9	0.52302 (12)	0.0199 (5)	0.28999 (10)	0.0353 (5)
C10	0.59134 (12)	−0.0856 (5)	0.26557 (11)	0.0374 (6)
C11	0.61151 (12)	−0.1687 (5)	0.19378 (10)	0.0338 (5)
C12	0.56158 (12)	−0.3235 (5)	0.14478 (11)	0.0375 (5)
H12	0.5125	−0.3693	0.1568	0.045*
C13	0.58354 (13)	−0.4110 (5)	0.07820 (11)	0.0378 (6)
H13	0.5495	−0.5174	0.0462	0.045*
C14	0.65592 (12)	−0.3404 (5)	0.05943 (10)	0.0363 (5)
C15	0.70668 (12)	−0.1831 (6)	0.10769 (11)	0.0401 (6)
H15	0.7552	−0.1315	0.0949	0.048*
C16	0.68528 (12)	−0.1036 (5)	0.17427 (11)	0.0391 (6)
H16	0.7201	−0.0057	0.2067	0.047*
C17	0.63265 (14)	−0.5648 (7)	−0.05674 (12)	0.0503 (7)
H17A	0.6587	−0.6058	−0.0989	0.075*
H17B	0.5915	−0.4073	−0.0667	0.075*
H17C	0.6136	−0.7813	−0.0398	0.075*
O1	0.65026 (9)	−0.1081 (5)	0.31159 (8)	0.0537 (5)
H1	0.6368	−0.0636	0.3512	0.081*
O2	0.56922 (10)	0.0915 (5)	0.40994 (8)	0.0609 (5)
O3	0.42812 (9)	0.0644 (4)	0.19222 (8)	0.0477 (5)
O4	0.68340 (9)	−0.4164 (4)	−0.00444 (7)	0.0470 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0489 (15)	0.0397 (14)	0.0407 (13)	−0.0010 (11)	0.0010 (12)	0.0020 (10)
C2	0.0521 (15)	0.0316 (13)	0.0389 (12)	−0.0033 (11)	0.0086 (11)	0.0000 (10)
C3	0.0693 (19)	0.0524 (16)	0.0443 (14)	−0.0007 (14)	0.0100 (13)	0.0003 (12)
C4	0.0665 (19)	0.0485 (16)	0.0553 (16)	0.0035 (14)	0.0233 (14)	−0.0022 (12)
C5	0.0532 (16)	0.0361 (14)	0.0661 (18)	0.0039 (12)	0.0179 (14)	0.0051 (12)
C6	0.0484 (15)	0.0346 (14)	0.0520 (14)	0.0016 (11)	0.0074 (12)	0.0033 (10)
C7	0.0459 (15)	0.0246 (12)	0.0407 (12)	−0.0029 (10)	0.0057 (11)	0.0026 (9)
C8	0.0479 (14)	0.0245 (12)	0.0376 (13)	−0.0026 (10)	0.0037 (11)	0.0050 (9)
C9	0.0403 (14)	0.0312 (12)	0.0344 (12)	0.0012 (10)	0.0010 (10)	−0.0003 (9)
C10	0.0414 (14)	0.0291 (12)	0.0410 (12)	−0.0007 (10)	−0.0053 (11)	0.0015 (9)
C11	0.0369 (13)	0.0255 (11)	0.0389 (12)	0.0034 (10)	−0.0010 (10)	0.0034 (9)
C12	0.0366 (13)	0.0303 (12)	0.0459 (13)	−0.0029 (10)	0.0048 (11)	0.0022 (10)
C13	0.0431 (14)	0.0307 (12)	0.0393 (12)	−0.0037 (10)	0.0000 (11)	−0.0017 (9)
C14	0.0418 (14)	0.0281 (12)	0.0390 (12)	0.0042 (10)	0.0035 (11)	0.0043 (9)
C15	0.0336 (13)	0.0383 (13)	0.0488 (13)	−0.0013 (10)	0.0052 (11)	0.0060 (10)
C16	0.0379 (13)	0.0350 (13)	0.0438 (13)	−0.0011 (10)	−0.0045 (11)	0.0022 (10)
C17	0.0592 (16)	0.0494 (16)	0.0423 (13)	−0.0001 (12)	0.0042 (12)	−0.0057 (11)
O1	0.0471 (10)	0.0711 (13)	0.0420 (9)	0.0095 (9)	−0.0056 (8)	−0.0058 (8)
O2	0.0582 (12)	0.0835 (14)	0.0400 (9)	0.0096 (10)	−0.0059 (9)	−0.0056 (8)
O3	0.0501 (10)	0.0543 (11)	0.0384 (9)	0.0066 (8)	−0.0017 (8)	−0.0009 (7)
O4	0.0474 (10)	0.0535 (11)	0.0406 (9)	0.0002 (8)	0.0073 (8)	−0.0030 (7)

Geometric parameters (Å, º) top

C1—O2	1.243 (3)	C10—C11	1.465 (3)
C1—C9	1.454 (3)	C11—C12	1.387 (3)
C1—C2	1.476 (3)	C11—C16	1.404 (3)
C2—C7	1.389 (3)	C12—C13	1.386 (3)
C2—C3	1.390 (3)	C12—H12	0.9300
C3—C4	1.385 (4)	C13—C14	1.380 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.378 (3)	C14—O4	1.365 (2)
C4—H4	0.9300	C14—C15	1.392 (3)
C5—C6	1.382 (3)	C15—C16	1.376 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.378 (3)	C16—H16	0.9300
C6—H6	0.9300	C17—O4	1.427 (3)
C7—C8	1.496 (3)	C17—H17A	0.9600
C8—O3	1.226 (2)	C17—H17B	0.9600
C8—C9	1.475 (3)	C17—H17C	0.9600
C9—C10	1.384 (3)	O1—H1	0.8200
C10—O1	1.333 (2)

O2—C1—C9	125.6 (2)	O1—C10—C11	112.11 (19)
O2—C1—C2	125.6 (2)	C9—C10—C11	129.68 (19)
C9—C1—C2	108.71 (19)	C12—C11—C16	118.2 (2)
C7—C2—C3	121.2 (2)	C12—C11—C10	122.7 (2)
C7—C2—C1	108.22 (19)	C16—C11—C10	119.01 (19)
C3—C2—C1	130.6 (2)	C13—C12—C11	121.1 (2)
C4—C3—C2	117.6 (2)	C13—C12—H12	119.4
C4—C3—H3	121.2	C11—C12—H12	119.4
C2—C3—H3	121.2	C14—C13—C12	120.0 (2)
C5—C4—C3	120.9 (2)	C14—C13—H13	120.0
C5—C4—H4	119.5	C12—C13—H13	120.0
C3—C4—H4	119.5	O4—C14—C13	124.76 (19)
C4—C5—C6	121.6 (2)	O4—C14—C15	115.50 (19)
C4—C5—H5	119.2	C13—C14—C15	119.7 (2)
C6—C5—H5	119.2	C16—C15—C14	120.2 (2)
C7—C6—C5	117.9 (2)	C16—C15—H15	119.9
C7—C6—H6	121.0	C14—C15—H15	119.9
C5—C6—H6	121.0	C15—C16—C11	120.7 (2)
C6—C7—C2	120.8 (2)	C15—C16—H16	119.6
C6—C7—C8	129.5 (2)	C11—C16—H16	119.6
C2—C7—C8	109.7 (2)	O4—C17—H17A	109.5
O3—C8—C9	130.1 (2)	O4—C17—H17B	109.5
O3—C8—C7	123.5 (2)	H17A—C17—H17B	109.5
C9—C8—C7	106.35 (17)	O4—C17—H17C	109.5
C10—C9—C1	120.02 (19)	H17A—C17—H17C	109.5
C10—C9—C8	132.62 (19)	H17B—C17—H17C	109.5
C1—C9—C8	107.00 (19)	C10—O1—H1	109.5
O1—C10—C9	118.17 (18)	C14—O4—C17	117.63 (17)

O2—C1—C2—C7	176.0 (2)	C7—C8—C9—C10	−172.1 (2)
C9—C1—C2—C7	−1.1 (2)	O3—C8—C9—C1	−179.1 (2)
O2—C1—C2—C3	−3.3 (4)	C7—C8—C9—C1	0.9 (2)
C9—C1—C2—C3	179.6 (2)	C1—C9—C10—O1	1.6 (3)
C7—C2—C3—C4	−0.9 (4)	C8—C9—C10—O1	173.8 (2)
C1—C2—C3—C4	178.3 (2)	C1—C9—C10—C11	−175.8 (2)
C2—C3—C4—C5	0.0 (4)	C8—C9—C10—C11	−3.6 (4)
C3—C4—C5—C6	0.3 (4)	O1—C10—C11—C12	148.4 (2)
C4—C5—C6—C7	0.3 (3)	C9—C10—C11—C12	−34.1 (3)
C5—C6—C7—C2	−1.3 (3)	O1—C10—C11—C16	−28.8 (3)
C5—C6—C7—C8	179.4 (2)	C9—C10—C11—C16	148.8 (2)
C3—C2—C7—C6	1.6 (3)	C16—C11—C12—C13	−0.2 (3)
C1—C2—C7—C6	−177.80 (19)	C10—C11—C12—C13	−177.40 (18)
C3—C2—C7—C8	−179.0 (2)	C11—C12—C13—C14	−0.8 (3)
C1—C2—C7—C8	1.6 (2)	C12—C13—C14—O4	179.78 (18)
C6—C7—C8—O3	−2.3 (4)	C12—C13—C14—C15	0.4 (3)
C2—C7—C8—O3	178.4 (2)	O4—C14—C15—C16	−178.35 (18)
C6—C7—C8—C9	177.8 (2)	C13—C14—C15—C16	1.1 (3)
C2—C7—C8—C9	−1.6 (2)	C14—C15—C16—C11	−2.2 (3)
O2—C1—C9—C10	−3.0 (3)	C12—C11—C16—C15	1.7 (3)
C2—C1—C9—C10	174.07 (19)	C10—C11—C16—C15	179.00 (18)
O2—C1—C9—C8	−177.0 (2)	C13—C14—O4—C17	3.1 (3)
C2—C1—C9—C8	0.1 (2)	C15—C14—O4—C17	−177.49 (19)
O3—C8—C9—C10	8.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.78	2.539 (2)	152

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂O₄
M_r	280.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	17.779 (4), 3.8405 (9), 19.026 (4)
β (°)	92.984 (8)
V (Å³)	1297.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.977, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	10521, 2311, 1553
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.127, 0.97
No. of reflections	2311
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.783	2.539 (2)	152.37

Acknowledgements

This work was supported financially by the Natural Science Foundation of China (No. 21061003) and the International Cooperation Foundation of Guizhou Province (No. 2009700104).

References

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