4-[(4-Chloro-phen-yl)(hy-droxy)methyl-idene]isochromane-1,3-dione.

In the title compound, C(16)H(9)ClO(4), the six-membered heterocyclic ring adopts a screw-boat conformation. The benzene rings are oriented to each other at a dihedral angle of 59.26 (9)°. The mol-ecular structure exhibits a ring motif, viz. S(6), owing to an intra-molecular O-H⋯O hydrogen bond. The presence of C-H⋯O contacts generates an infinite chain along [001]. Also present are π-π stacking inter-actions between neighbouring isochromanedione benzene rings [centroid-centroid distance = 3.746 (1) Å], and C-O⋯π inter-actions [O⋯centroid = 3.934 (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 puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H9ClO4

M = 300.68

Monoclinic,

a = 15.4973 (4) Å

b = 5.9631 (1) Å

c = 14.4526 (3) Å

β = 102.661 (1)°

V = 1303.12 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 298 K

0.40 × 0.30 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

12213 measured reflections

3248 independent reflections

2693 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.163

S = 1.08

3248 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.31 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); 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/S160053681104829X/tk5016sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104829X/tk5016Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104829X/tk5016Isup3.cml

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

C16H9ClO4	F(000) = 616
Mr = 300.68	Dx = 1.533 Mg m−3
Monoclinic, P21/c	Melting point = 432–433 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.4973 (4) Å	Cell parameters from 12213 reflections
b = 5.9631 (1) Å	θ = 1.4–29.0°
c = 14.4526 (3) Å	µ = 0.31 mm−1
β = 102.661 (1)°	T = 298 K
V = 1303.12 (5) Å3	Prism, yellow
Z = 4	0.40 × 0.30 × 0.20 mm

Nonius KappaCCD diffractometer	2693 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
graphite	θmax = 29.0°, θmin = 1.4°
φ and ω scans	h = −20→20
12213 measured reflections	k = −7→7
3248 independent reflections	l = −19→19

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.085P)2 + 0.4082P] where P = (Fo2 + 2Fc2)/3
3248 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.31 e Å−3
36 constraints

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. 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 > 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
Cl21	0.46136 (4)	0.22385 (12)	0.41605 (4)	0.0768 (3)
O8	0.15001 (11)	0.2734 (3)	−0.20791 (9)	0.0600 (4)
C1	0.16846 (10)	0.1431 (3)	−0.01749 (10)	0.0355 (3)
C6	0.11986 (11)	0.0094 (3)	−0.09040 (10)	0.0412 (4)
O12	0.22812 (11)	0.5783 (3)	−0.16990 (11)	0.0688 (5)
C2	0.16289 (11)	0.0881 (3)	0.07551 (10)	0.0391 (4)
H2	0.1898	0.1804	0.1254	0.047*
C10	0.21737 (11)	0.3377 (3)	−0.04175 (11)	0.0401 (4)
O14	0.30865 (10)	0.6583 (2)	−0.00417 (11)	0.0631 (4)
H14	0.2881	0.6813	−0.0606	0.095*
C7	0.11070 (14)	0.0730 (3)	−0.18995 (12)	0.0525 (5)
C13	0.27868 (11)	0.4635 (3)	0.02079 (13)	0.0437 (4)
C19	0.40760 (12)	0.1419 (3)	0.22901 (14)	0.0479 (4)
H19	0.4368	0.0053	0.2416	0.057*
O11	0.07046 (13)	−0.0255 (3)	−0.25801 (10)	0.0769 (5)
C5	0.07423 (13)	−0.1807 (3)	−0.07083 (13)	0.0507 (4)
H5	0.0429	−0.2681	−0.1203	0.061*
C4	0.07567 (13)	−0.2382 (3)	0.02135 (15)	0.0521 (5)
H4	0.0482	−0.3690	0.0349	0.062*
C16	0.32267 (13)	0.5515 (3)	0.19262 (14)	0.0504 (4)
H16	0.2949	0.6900	0.1802	0.060*
C15	0.32154 (11)	0.4012 (3)	0.11887 (12)	0.0413 (4)
C20	0.36492 (12)	0.1967 (3)	0.13808 (13)	0.0452 (4)
H20	0.3651	0.0961	0.0889	0.054*
C17	0.36473 (13)	0.4967 (3)	0.28416 (14)	0.0547 (5)
H17	0.3648	0.5966	0.3336	0.066*
C3	0.11838 (12)	−0.1000 (3)	0.09398 (12)	0.0454 (4)
H3	0.1169	−0.1350	0.1563	0.054*
C18	0.40658 (12)	0.2924 (3)	0.30156 (13)	0.0484 (4)
C9	0.19987 (13)	0.4065 (3)	−0.13974 (12)	0.0499 (4)

	U11	U22	U33	U12	U13	U23
Cl21	0.0704 (4)	0.1024 (5)	0.0503 (3)	0.0049 (3)	−0.0029 (3)	0.0100 (3)
O8	0.0778 (10)	0.0730 (10)	0.0291 (6)	0.0145 (7)	0.0118 (6)	0.0079 (6)
C1	0.0389 (7)	0.0382 (8)	0.0293 (7)	0.0059 (6)	0.0070 (6)	−0.0002 (5)
C6	0.0459 (8)	0.0452 (9)	0.0303 (7)	0.0107 (7)	0.0032 (6)	−0.0060 (6)
O12	0.0821 (11)	0.0719 (10)	0.0570 (8)	0.0075 (8)	0.0251 (7)	0.0298 (7)
C2	0.0427 (8)	0.0448 (9)	0.0290 (7)	−0.0061 (6)	0.0059 (6)	−0.0030 (6)
C10	0.0452 (8)	0.0422 (8)	0.0347 (7)	0.0065 (6)	0.0124 (6)	0.0057 (6)
O14	0.0663 (9)	0.0489 (8)	0.0720 (10)	−0.0103 (7)	0.0107 (7)	0.0188 (7)
C7	0.0646 (11)	0.0585 (11)	0.0313 (8)	0.0215 (9)	0.0034 (7)	−0.0057 (7)
C13	0.0444 (8)	0.0379 (8)	0.0508 (9)	0.0024 (6)	0.0147 (7)	0.0074 (7)
C19	0.0424 (8)	0.0427 (9)	0.0569 (10)	0.0037 (7)	0.0075 (7)	0.0054 (7)
O11	0.1078 (13)	0.0786 (11)	0.0337 (7)	0.0195 (9)	−0.0076 (7)	−0.0149 (7)
C5	0.0531 (10)	0.0472 (10)	0.0456 (9)	0.0004 (8)	−0.0030 (7)	−0.0133 (7)
C4	0.0534 (10)	0.0446 (10)	0.0550 (11)	−0.0112 (8)	0.0052 (8)	−0.0023 (8)
C16	0.0512 (10)	0.0372 (9)	0.0597 (11)	0.0044 (7)	0.0056 (8)	−0.0054 (7)
C15	0.0384 (8)	0.0365 (8)	0.0483 (9)	−0.0032 (6)	0.0081 (7)	0.0014 (6)
C20	0.0472 (9)	0.0387 (9)	0.0493 (9)	0.0025 (7)	0.0097 (7)	−0.0033 (7)
C17	0.0549 (11)	0.0544 (11)	0.0523 (10)	0.0022 (8)	0.0068 (8)	−0.0133 (8)
C3	0.0476 (9)	0.0502 (10)	0.0376 (8)	−0.0064 (7)	0.0074 (7)	0.0035 (7)
C18	0.0384 (8)	0.0576 (11)	0.0473 (9)	−0.0039 (7)	0.0054 (7)	0.0028 (8)
C9	0.0552 (10)	0.0583 (11)	0.0392 (8)	0.0153 (8)	0.0171 (7)	0.0120 (7)

Cl21—C18	1.7349 (19)	C13—C15	1.475 (2)
O8—C9	1.365 (3)	C19—C20	1.375 (3)
O8—C7	1.391 (3)	C19—C18	1.383 (3)
C1—C6	1.402 (2)	C19—H19	0.9300
C1—C2	1.405 (2)	C5—C4	1.371 (3)
C1—C10	1.469 (2)	C5—H5	0.9300
C6—C5	1.397 (3)	C4—C3	1.384 (3)
C6—C7	1.465 (2)	C4—H4	0.9300
O12—C9	1.231 (2)	C16—C17	1.380 (3)
C2—C3	1.373 (2)	C16—C15	1.390 (2)
C2—H2	0.9300	C16—H16	0.9300
C10—C13	1.381 (2)	C15—C20	1.390 (2)
C10—C9	1.442 (2)	C20—H20	0.9300
O14—C13	1.330 (2)	C17—C18	1.377 (3)
O14—H14	0.8200	C17—H17	0.9300
C7—O11	1.197 (2)	C3—H3	0.9300
C9—O8—C7	124.50 (14)	C6—C5—H5	120.1
C6—C1—C2	116.77 (15)	C5—C4—C3	119.43 (17)
C6—C1—C10	119.35 (14)	C5—C4—H4	120.3
C2—C1—C10	123.78 (14)	C3—C4—H4	120.3
C5—C6—C1	121.45 (15)	C17—C16—C15	120.40 (17)
C5—C6—C7	117.68 (16)	C17—C16—H16	119.8
C1—C6—C7	120.75 (17)	C15—C16—H16	119.8
C3—C2—C1	121.06 (15)	C16—C15—C20	119.22 (16)
C3—C2—H2	119.5	C16—C15—C13	120.09 (16)
C1—C2—H2	119.5	C20—C15—C13	120.61 (16)
C13—C10—C9	116.26 (16)	C19—C20—C15	120.63 (17)
C13—C10—C1	126.15 (14)	C19—C20—H20	119.7
C9—C10—C1	117.58 (15)	C15—C20—H20	119.7
C13—O14—H14	109.5	C18—C17—C16	119.31 (18)
O11—C7—O8	116.02 (18)	C18—C17—H17	120.3
O11—C7—C6	127.0 (2)	C16—C17—H17	120.3
O8—C7—C6	116.98 (16)	C2—C3—C4	121.07 (16)
O14—C13—C10	121.90 (16)	C2—C3—H3	119.5
O14—C13—C15	111.74 (16)	C4—C3—H3	119.5
C10—C13—C15	126.31 (15)	C17—C18—C19	121.25 (18)
C20—C19—C18	119.17 (17)	C17—C18—Cl21	119.68 (16)
C20—C19—H19	120.4	C19—C18—Cl21	119.05 (15)
C18—C19—H19	120.4	O12—C9—O8	114.66 (16)
C4—C5—C6	119.89 (16)	O12—C9—C10	125.43 (19)
C4—C5—H5	120.1	O8—C9—C10	119.89 (17)
C2—C1—C6—C5	−5.3 (2)	C17—C16—C15—C20	−1.4 (3)
C10—C1—C6—C5	178.26 (15)	C17—C16—C15—C13	−178.23 (17)
C2—C1—C6—C7	170.79 (15)	O14—C13—C15—C16	52.6 (2)
C10—C1—C6—C7	−5.7 (2)	C10—C13—C15—C16	−129.9 (2)
C6—C1—C2—C3	5.7 (2)	O14—C13—C15—C20	−124.18 (18)
C10—C1—C2—C3	−177.98 (15)	C10—C13—C15—C20	53.3 (2)
C6—C1—C10—C13	−169.15 (16)	C18—C19—C20—C15	0.3 (3)
C2—C1—C10—C13	14.6 (3)	C16—C15—C20—C19	0.8 (3)
C6—C1—C10—C9	11.3 (2)	C13—C15—C20—C19	177.65 (16)
C2—C1—C10—C9	−164.88 (16)	C15—C16—C17—C18	0.8 (3)
C9—O8—C7—O11	−178.66 (18)	C1—C2—C3—C4	−1.7 (3)
C9—O8—C7—C6	3.6 (3)	C5—C4—C3—C2	−3.1 (3)
C5—C6—C7—O11	−3.0 (3)	C16—C17—C18—C19	0.3 (3)
C1—C6—C7—O11	−179.20 (19)	C16—C17—C18—Cl21	178.84 (15)
C5—C6—C7—O8	174.43 (15)	C20—C19—C18—C17	−0.9 (3)
C1—C6—C7—O8	−1.8 (2)	C20—C19—C18—Cl21	−179.41 (14)
C9—C10—C13—O14	11.1 (3)	C7—O8—C9—O12	−179.24 (16)
C1—C10—C13—O14	−168.40 (16)	C7—O8—C9—C10	2.3 (3)
C9—C10—C13—C15	−166.14 (16)	C13—C10—C9—O12	−7.6 (3)
C1—C10—C13—C15	14.3 (3)	C1—C10—C9—O12	172.00 (17)
C1—C6—C5—C4	0.7 (3)	C13—C10—C9—O8	170.70 (16)
C7—C6—C5—C4	−175.45 (18)	C1—C10—C9—O8	−9.7 (2)
C6—C5—C4—C3	3.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O12	0.82	1.76	2.492 (2)	148
C3—H3···O11i	0.93	2.56	3.288 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O14—H14⋯O12	0.82	1.76	2.492 (2)	148
C3—H3⋯O11i	0.93	2.56	3.288 (2)	136

Symmetry code: (i) .