4-[(Hy-droxy)(4-methyl-phen-yl)methyl-idene]isochroman-1,3-dione.

In the title compound, C(17)H(12)O(4), the six-membered heterocyclic ring adopts a distorted screw-boat conformation. The mol-ecular structure exhibits an S(6) ring motif, owing to an intra-molecular O-H⋯O hydrogen bond. In the crystal, weak C-H⋯O contacts generate an infinite chain along the c axis. There are also π-π stacking inter-actions between neighbouring isochromanedione benzene rings, with a centroid-centroid distance of 3.755 (1) Å, and C-O⋯π inter-actions with an O⋯centroid distance of 3.964 (2) Å.

Related literature

For the biological activity of isochromanones, see: Bianchi et al., (2004 ▶); Buntin et al. (2008 ▶). For π–π stacking inter­actions, see: Janiak (2000 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H12O4

M = 280.27

Monoclinic,

a = 15.6767 (6) Å

b = 5.9655 (2) Å

c = 14.4589 (4) Å

β = 102.961 (1)°

V = 1317.74 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.40 × 0.34 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

12419 measured reflections

3304 independent reflections

2684 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.150

S = 1.08

3304 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050975/fj2488sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050975/fj2488Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050975/fj2488Isup3.cml

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

C17H12O4	F(000) = 584
Mr = 280.27	Dx = 1.413 Mg m−3
Monoclinic, P21/c	Melting point = 387–388 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.6767 (6) Å	Cell parameters from 12419 reflections
b = 5.9655 (2) Å	θ = 2.9–29.0°
c = 14.4589 (4) Å	µ = 0.10 mm−1
β = 102.961 (1)°	T = 298 K
V = 1317.74 (8) Å3	Prism, yellow
Z = 4	0.40 × 0.34 × 0.10 mm

Nonius KappaCCD diffractometer	2684 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
graphite	θmax = 29.0°, θmin = 2.9°
φ and ω scans	h = −21→20
12419 measured reflections	k = −7→7
3304 independent reflections	l = −19→19

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.424P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3304 reflections	Δρmax = 0.20 e Å−3
193 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
48 constraints	Extinction coefficient: 0.11 (2)
Primary atom site location: structure-invariant direct methods

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

Refinement. The 2 reflections [(-5 2 1), (2 0 0)] whith (Iobs-Icalc)/Sigma(I) superior to 10, are not used in the refinement. 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 > 2σ(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	0.85227 (9)	0.2252 (2)	0.70711 (8)	0.0608 (4)
C5	0.83327 (9)	0.3569 (2)	0.51682 (9)	0.0361 (3)
C4	0.88171 (10)	0.4900 (3)	0.59015 (10)	0.0420 (4)
O3	0.77485 (10)	−0.0788 (3)	0.66859 (10)	0.0690 (4)
O4	0.69333 (9)	−0.1556 (2)	0.50349 (10)	0.0632 (4)
H4	0.7147	−0.1802	0.5597	0.095*
C15	0.59439 (11)	0.3609 (3)	0.27099 (12)	0.0484 (4)
H15	0.5656	0.4979	0.2599	0.058*
C1	0.78494 (10)	0.1628 (3)	0.54105 (10)	0.0405 (4)
C6	0.83808 (10)	0.4128 (3)	0.42383 (10)	0.0401 (4)
H6	0.8110	0.3211	0.3738	0.048*
C9	0.92667 (11)	0.6800 (3)	0.57079 (12)	0.0514 (4)
H9	0.9579	0.7670	0.6204	0.062*
C16	0.63851 (10)	0.3071 (3)	0.36170 (12)	0.0454 (4)
H16	0.6403	0.4089	0.4108	0.054*
C11	0.68042 (10)	0.1011 (3)	0.38016 (11)	0.0412 (4)
C10	0.72372 (10)	0.0383 (3)	0.47841 (12)	0.0441 (4)
C12	0.67731 (11)	−0.0477 (3)	0.30589 (13)	0.0515 (4)
H12	0.7043	−0.1870	0.3173	0.062*
C8	0.92474 (12)	0.7385 (3)	0.47832 (13)	0.0530 (4)
H8	0.9519	0.8693	0.4648	0.064*
C3	0.89085 (12)	0.4261 (3)	0.68931 (11)	0.0532 (5)
O2	0.93083 (11)	0.5246 (3)	0.75773 (9)	0.0782 (5)
C14	0.59194 (10)	0.2147 (3)	0.19552 (12)	0.0487 (4)
C13	0.63411 (12)	0.0107 (3)	0.21485 (13)	0.0567 (5)
H13	0.6334	−0.0896	0.1654	0.068*
C7	0.88200 (11)	0.6007 (3)	0.40553 (11)	0.0461 (4)
H7	0.8831	0.6360	0.3432	0.055*
C2	0.80260 (12)	0.0934 (3)	0.63907 (12)	0.0504 (4)
C17	0.54283 (14)	0.2771 (4)	0.09711 (14)	0.0719 (6)
H17A	0.4814	0.2511	0.0913	0.108*
H17B	0.5634	0.1874	0.0514	0.108*
H17C	0.5524	0.4327	0.0859	0.108*

	U11	U22	U33	U12	U13	U23
O1	0.0781 (9)	0.0731 (9)	0.0303 (6)	0.0141 (7)	0.0104 (5)	0.0079 (5)
C5	0.0390 (7)	0.0374 (8)	0.0311 (7)	0.0060 (5)	0.0063 (5)	−0.0008 (5)
C4	0.0461 (8)	0.0458 (9)	0.0313 (7)	0.0105 (6)	0.0029 (6)	−0.0061 (6)
O3	0.0837 (10)	0.0700 (9)	0.0572 (8)	0.0078 (7)	0.0242 (7)	0.0287 (7)
O4	0.0656 (8)	0.0478 (7)	0.0736 (9)	−0.0084 (6)	0.0102 (7)	0.0191 (6)
C15	0.0448 (8)	0.0428 (9)	0.0566 (10)	0.0044 (7)	0.0092 (7)	0.0052 (7)
C1	0.0452 (8)	0.0419 (8)	0.0357 (7)	0.0064 (6)	0.0116 (6)	0.0047 (6)
C6	0.0435 (8)	0.0450 (8)	0.0306 (7)	−0.0051 (6)	0.0056 (6)	−0.0029 (6)
C9	0.0527 (9)	0.0473 (9)	0.0474 (9)	−0.0001 (7)	−0.0031 (7)	−0.0147 (7)
C16	0.0481 (8)	0.0383 (8)	0.0491 (9)	0.0034 (6)	0.0094 (7)	−0.0026 (6)
C11	0.0382 (7)	0.0355 (8)	0.0482 (8)	−0.0021 (6)	0.0064 (6)	0.0002 (6)
C10	0.0463 (8)	0.0371 (8)	0.0509 (9)	0.0039 (6)	0.0149 (7)	0.0069 (6)
C12	0.0520 (9)	0.0383 (9)	0.0606 (10)	0.0032 (7)	0.0048 (8)	−0.0059 (7)
C8	0.0551 (10)	0.0438 (9)	0.0567 (10)	−0.0094 (7)	0.0053 (8)	−0.0031 (7)
C3	0.0648 (11)	0.0583 (11)	0.0328 (8)	0.0203 (8)	0.0030 (7)	−0.0057 (7)
O2	0.1091 (12)	0.0797 (10)	0.0345 (6)	0.0199 (9)	−0.0081 (7)	−0.0154 (6)
C14	0.0380 (8)	0.0586 (10)	0.0478 (9)	−0.0055 (7)	0.0060 (6)	0.0021 (7)
C13	0.0563 (10)	0.0564 (11)	0.0544 (10)	−0.0008 (8)	0.0059 (8)	−0.0161 (8)
C7	0.0487 (9)	0.0504 (9)	0.0380 (8)	−0.0070 (7)	0.0069 (6)	0.0024 (6)
C2	0.0563 (10)	0.0564 (10)	0.0414 (8)	0.0153 (8)	0.0169 (7)	0.0108 (7)
C17	0.0641 (12)	0.0963 (17)	0.0503 (11)	−0.0034 (11)	0.0024 (9)	0.0090 (10)

O1—C2	1.360 (2)	C9—H9	0.9300
O1—C3	1.392 (2)	C16—C11	1.391 (2)
C5—C4	1.404 (2)	C16—H16	0.9300
C5—C6	1.404 (2)	C11—C12	1.386 (2)
C5—C1	1.469 (2)	C11—C10	1.479 (2)
C4—C9	1.396 (2)	C12—C13	1.383 (3)
C4—C3	1.459 (2)	C12—H12	0.9300
O3—C2	1.229 (2)	C8—C7	1.384 (2)
O4—C10	1.3316 (19)	C8—H8	0.9300
O4—H4	0.8200	C3—O2	1.199 (2)
C15—C16	1.376 (2)	C14—C13	1.383 (3)
C15—C14	1.391 (2)	C14—C17	1.505 (2)
C15—H15	0.9300	C13—H13	0.9300
C1—C10	1.380 (2)	C7—H7	0.9300
C1—C2	1.443 (2)	C17—H17A	0.9600
C6—C7	1.372 (2)	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C9—C8	1.376 (3)
C2—O1—C3	124.49 (13)	C1—C10—C11	126.59 (14)
C4—C5—C6	116.93 (14)	C13—C12—C11	120.05 (16)
C4—C5—C1	119.11 (13)	C13—C12—H12	120.0
C6—C5—C1	123.87 (13)	C11—C12—H12	120.0
C9—C4—C5	121.33 (14)	C9—C8—C7	119.32 (16)
C9—C4—C3	117.80 (15)	C9—C8—H8	120.3
C5—C4—C3	120.78 (16)	C7—C8—H8	120.3
C10—O4—H4	109.5	O2—C3—O1	115.94 (16)
C16—C15—C14	121.40 (16)	O2—C3—C4	126.9 (2)
C16—C15—H15	119.3	O1—C3—C4	117.10 (15)
C14—C15—H15	119.3	C13—C14—C15	117.73 (15)
C10—C1—C2	116.26 (15)	C13—C14—C17	121.93 (18)
C10—C1—C5	126.02 (13)	C15—C14—C17	120.32 (17)
C2—C1—C5	117.72 (14)	C12—C13—C14	121.58 (16)
C7—C6—C5	121.07 (14)	C12—C13—H13	119.2
C7—C6—H6	119.5	C14—C13—H13	119.2
C5—C6—H6	119.5	C6—C7—C8	121.13 (15)
C8—C9—C4	119.92 (15)	C6—C7—H7	119.4
C8—C9—H9	120.0	C8—C7—H7	119.4
C4—C9—H9	120.0	O3—C2—O1	114.97 (15)
C15—C16—C11	120.24 (16)	O3—C2—C1	125.20 (18)
C15—C16—H16	119.9	O1—C2—C1	119.82 (16)
C11—C16—H16	119.9	C14—C17—H17A	109.5
C12—C11—C16	118.97 (15)	C14—C17—H17B	109.5
C12—C11—C10	120.72 (14)	H17A—C17—H17B	109.5
C16—C11—C10	120.24 (15)	C14—C17—H17C	109.5
O4—C10—C1	121.84 (15)	H17A—C17—H17C	109.5
O4—C10—C11	111.50 (14)	H17B—C17—H17C	109.5
C6—C5—C4—C9	5.1 (2)	C16—C11—C12—C13	0.9 (3)
C1—C5—C4—C9	−178.11 (14)	C10—C11—C12—C13	177.89 (16)
C6—C5—C4—C3	−171.19 (14)	C4—C9—C8—C7	−3.5 (3)
C1—C5—C4—C3	5.6 (2)	C2—O1—C3—O2	178.20 (16)
C4—C5—C1—C10	168.82 (15)	C2—O1—C3—C4	−4.3 (2)
C6—C5—C1—C10	−14.7 (2)	C9—C4—C3—O2	3.0 (3)
C4—C5—C1—C2	−11.4 (2)	C5—C4—C3—O2	179.43 (17)
C6—C5—C1—C2	165.14 (14)	C9—C4—C3—O1	−174.25 (14)
C4—C5—C6—C7	−5.5 (2)	C5—C4—C3—O1	2.2 (2)
C1—C5—C6—C7	177.88 (14)	C16—C15—C14—C13	1.2 (2)
C5—C4—C9—C8	−0.7 (2)	C16—C15—C14—C17	179.69 (16)
C3—C4—C9—C8	175.73 (16)	C11—C12—C13—C14	−1.1 (3)
C14—C15—C16—C11	−1.4 (3)	C15—C14—C13—C12	0.1 (3)
C15—C16—C11—C12	0.3 (2)	C17—C14—C13—C12	−178.41 (18)
C15—C16—C11—C10	−176.67 (15)	C5—C6—C7—C8	1.5 (3)
C2—C1—C10—O4	−10.7 (2)	C9—C8—C7—C6	3.2 (3)
C5—C1—C10—O4	169.10 (15)	C3—O1—C2—O3	179.33 (15)
C2—C1—C10—C11	165.94 (15)	C3—O1—C2—C1	−1.8 (2)
C5—C1—C10—C11	−14.3 (3)	C10—C1—C2—O3	8.2 (2)
C12—C11—C10—O4	−52.7 (2)	C5—C1—C2—O3	−171.65 (16)
C16—C11—C10—O4	124.25 (16)	C10—C1—C2—O1	−170.55 (14)
C12—C11—C10—C1	130.41 (18)	C5—C1—C2—O1	9.6 (2)
C16—C11—C10—C1	−52.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	1.75	2.485 (2)	148
C7—H7···O2i	0.93	2.57	3.299 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.82	1.75	2.485 (2)	148
C7—H7⋯O2i	0.93	2.57	3.299 (2)	136

Symmetry code: (i) .