Crystal structure of 2-hy-droxy-2-(2-oxo-cyclo-hept-yl)-2,3-di-hydro-1H-indene-1,3-dione.

In the title compound, C16H16O4, the five-membered ring of the indene-1,3-dione unit adopts a twist conformation, whereas the seven-membered ring adopts a twist-chair conformation. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, weak C-H⋯O hydrogen bonds and π-π stacking [centroid-to-centroid distance = 3.7373 (8) Å] into a three-dimensional supra-molecular architecture.

Related literature

For the background and potential applications of the title compound, see: Andreu et al. (2009 ▸); Fun et al. (2009 ▸); Ghalib et al. (2011 ▸); Uk Kim et al. (2004 ▸); Penthala et al. (2009 ▸); Sundar et al. (2010 ▸); Yao et al. (2006a ▸,b ▸).

Experimental

Crystal data

C16H16O4

M = 272.29

Orthorhombic,

a = 7.4131 (5) Å

b = 18.8596 (13) Å

c = 19.0166 (13) Å

V = 2658.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.30 × 0.23 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.978, T max = 0.986

28734 measured reflections

3191 independent reflections

2849 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.03

3191 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015016126/xu5867sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016126/xu5867Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016126/xu5867Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016126/xu5867Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015016126/xu5867fig1.tif

The mol­ecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.

Click here for additional data file.

a . DOI: 10.1107/S2056989015016126/xu5867fig2.tif

A view of the mol­ecular aggregation down the a axis. Ring systems and H atoms that are not involved in hydrogen bonding have been omitted for clarity.

CCDC reference: 1421141

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H16O4	Dx = 1.361 Mg m−3Dm = 1.35 Mg m−3Dm measured by floatation method
Mr = 272.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7469 reflections
a = 7.4131 (5) Å	θ = 2.4–27.8°
b = 18.8596 (13) Å	µ = 0.10 mm−1
c = 19.0166 (13) Å	T = 294 K
V = 2658.7 (3) Å3	Needle, colourless
Z = 8	0.30 × 0.23 × 0.18 mm
F(000) = 1152

Bruker SMART APEXII CCD diffractometer	2849 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
φ and ω scans	θmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.978, Tmax = 0.986	k = −24→24
28734 measured reflections	l = −24→25
3191 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0599P)2 + 0.7812P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3191 reflections	Δρmax = 0.33 e Å−3
185 parameters	Δρmin = −0.20 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.

	x	y	z	Uiso*/Ueq
O1	1.03172 (15)	0.08184 (7)	0.44453 (5)	0.0593 (3)
O2	0.56285 (14)	0.19613 (6)	0.45415 (5)	0.0525 (3)
O3	0.60520 (16)	0.04223 (5)	0.41294 (5)	0.0565 (3)
O4	0.93803 (17)	0.25552 (5)	0.41716 (5)	0.0570 (3)
C1	0.68387 (16)	0.09552 (6)	0.39677 (6)	0.0357 (3)
C2	0.73825 (16)	0.11650 (6)	0.32474 (6)	0.0343 (3)
C3	0.70883 (18)	0.08049 (8)	0.26203 (7)	0.0446 (3)
H3	0.6582	0.0354	0.2617	0.053*
C4	0.75714 (19)	0.11383 (9)	0.20020 (7)	0.0509 (4)
H4	0.7383	0.0908	0.1576	0.061*
C5	0.83328 (19)	0.18099 (9)	0.20053 (6)	0.0487 (3)
H5	0.8608	0.2028	0.1580	0.058*
C6	0.86906 (18)	0.21611 (7)	0.26286 (6)	0.0427 (3)
H6	0.9238	0.2605	0.2631	0.051*
C7	0.82010 (16)	0.18254 (6)	0.32509 (6)	0.0335 (2)
C8	0.84477 (17)	0.20639 (6)	0.39815 (6)	0.0355 (3)
C9	0.72848 (16)	0.15854 (6)	0.44602 (6)	0.0334 (2)
C10	0.81939 (16)	0.14094 (6)	0.51591 (6)	0.0343 (2)
H10	0.8396	0.1855	0.5412	0.041*
C11	0.70788 (19)	0.09172 (7)	0.56410 (7)	0.0434 (3)
H11A	0.5807	0.1009	0.5563	0.052*
H11B	0.7312	0.0429	0.5509	0.052*
C12	0.7486 (3)	0.10069 (9)	0.64220 (7)	0.0589 (4)
H12A	0.7260	0.1497	0.6549	0.071*
H12B	0.6645	0.0716	0.6686	0.071*
C13	0.9388 (3)	0.08166 (10)	0.66515 (8)	0.0679 (5)
H13A	0.9607	0.0323	0.6534	0.081*
H13B	0.9459	0.0860	0.7159	0.081*
C14	1.0880 (2)	0.12630 (9)	0.63284 (8)	0.0594 (4)
H14A	1.1938	0.1232	0.6627	0.071*
H14B	1.0494	0.1754	0.6324	0.071*
C15	1.1415 (2)	0.10527 (8)	0.55851 (8)	0.0547 (4)
H15A	1.2401	0.1358	0.5441	0.066*
H15B	1.1886	0.0573	0.5604	0.066*
C16	1.00134 (17)	0.10759 (6)	0.50196 (7)	0.0380 (3)
H2	0.549 (3)	0.2103 (10)	0.4936 (11)	0.070 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0519 (6)	0.0860 (8)	0.0399 (5)	0.0216 (5)	0.0051 (4)	−0.0029 (5)
O2	0.0512 (6)	0.0737 (7)	0.0326 (5)	0.0284 (5)	0.0016 (4)	−0.0022 (4)
O3	0.0654 (7)	0.0510 (6)	0.0530 (6)	−0.0195 (5)	−0.0038 (5)	0.0066 (4)
O4	0.0843 (8)	0.0484 (5)	0.0381 (5)	−0.0224 (5)	−0.0097 (5)	−0.0021 (4)
C1	0.0347 (6)	0.0388 (6)	0.0335 (6)	0.0007 (4)	−0.0020 (4)	−0.0002 (4)
C2	0.0325 (5)	0.0405 (6)	0.0298 (5)	0.0033 (4)	−0.0018 (4)	−0.0050 (4)
C3	0.0420 (7)	0.0523 (7)	0.0394 (7)	0.0029 (5)	−0.0053 (5)	−0.0148 (5)
C4	0.0451 (7)	0.0768 (10)	0.0308 (6)	0.0108 (7)	−0.0049 (5)	−0.0160 (6)
C5	0.0429 (7)	0.0771 (9)	0.0261 (6)	0.0113 (6)	0.0019 (5)	0.0035 (6)
C6	0.0418 (6)	0.0535 (7)	0.0327 (6)	0.0011 (5)	0.0009 (5)	0.0058 (5)
C7	0.0340 (5)	0.0403 (6)	0.0261 (5)	0.0030 (4)	−0.0009 (4)	−0.0013 (4)
C8	0.0452 (6)	0.0337 (5)	0.0277 (5)	0.0015 (5)	−0.0028 (4)	−0.0005 (4)
C9	0.0367 (6)	0.0376 (5)	0.0258 (5)	0.0057 (4)	0.0017 (4)	−0.0003 (4)
C10	0.0399 (6)	0.0372 (6)	0.0257 (5)	0.0024 (5)	0.0003 (4)	0.0015 (4)
C11	0.0440 (7)	0.0514 (7)	0.0348 (6)	−0.0021 (5)	0.0044 (5)	0.0083 (5)
C12	0.0780 (11)	0.0668 (9)	0.0319 (6)	−0.0066 (8)	0.0087 (7)	0.0102 (6)
C13	0.0937 (13)	0.0668 (10)	0.0431 (8)	−0.0138 (9)	−0.0193 (8)	0.0195 (7)
C14	0.0743 (10)	0.0544 (8)	0.0494 (8)	−0.0069 (7)	−0.0244 (7)	0.0063 (6)
C15	0.0475 (8)	0.0568 (8)	0.0597 (9)	0.0069 (6)	−0.0157 (7)	−0.0008 (7)
C16	0.0379 (6)	0.0400 (6)	0.0360 (6)	0.0004 (5)	0.0017 (5)	0.0066 (5)

O1—C16	1.2163 (16)	C9—C10	1.5267 (15)
O2—C9	1.4262 (14)	C10—C16	1.5118 (17)
O2—H2	0.80 (2)	C10—C11	1.5442 (16)
O3—C1	1.2018 (15)	C10—H10	0.9800
O4—C8	1.2113 (15)	C11—C12	1.5249 (18)
C1—C2	1.4818 (16)	C11—H11A	0.9700
C1—C9	1.5489 (16)	C11—H11B	0.9700
C2—C7	1.3856 (17)	C12—C13	1.519 (3)
C2—C3	1.3894 (16)	C12—H12A	0.9700
C3—C4	1.381 (2)	C12—H12B	0.9700
C3—H3	0.9300	C13—C14	1.520 (3)
C4—C5	1.387 (2)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.3833 (18)	C14—C15	1.521 (2)
C5—H5	0.9300	C14—H14A	0.9700
C6—C7	1.3904 (16)	C14—H14B	0.9700
C6—H6	0.9300	C15—C16	1.4961 (19)
C7—C8	1.4718 (15)	C15—H15A	0.9700
C8—C9	1.5448 (16)	C15—H15B	0.9700
C9—O2—H2	112.0 (14)	C9—C10—H10	107.9
O3—C1—C2	126.28 (11)	C11—C10—H10	107.9
O3—C1—C9	126.20 (11)	C12—C11—C10	113.91 (12)
C2—C1—C9	107.22 (9)	C12—C11—H11A	108.8
C7—C2—C3	120.82 (11)	C10—C11—H11A	108.8
C7—C2—C1	110.77 (9)	C12—C11—H11B	108.8
C3—C2—C1	128.33 (12)	C10—C11—H11B	108.8
C4—C3—C2	117.88 (13)	H11A—C11—H11B	107.7
C4—C3—H3	121.1	C13—C12—C11	115.93 (14)
C2—C3—H3	121.1	C13—C12—H12A	108.3
C3—C4—C5	121.17 (12)	C11—C12—H12A	108.3
C3—C4—H4	119.4	C13—C12—H12B	108.3
C5—C4—H4	119.4	C11—C12—H12B	108.3
C6—C5—C4	121.29 (12)	H12A—C12—H12B	107.4
C6—C5—H5	119.4	C12—C13—C14	115.37 (13)
C4—C5—H5	119.4	C12—C13—H13A	108.4
C5—C6—C7	117.47 (13)	C14—C13—H13A	108.4
C5—C6—H6	121.3	C12—C13—H13B	108.4
C7—C6—H6	121.3	C14—C13—H13B	108.4
C2—C7—C6	121.30 (11)	H13A—C13—H13B	107.5
C2—C7—C8	109.50 (10)	C13—C14—C15	114.90 (14)
C6—C7—C8	129.20 (11)	C13—C14—H14A	108.5
O4—C8—C7	125.90 (11)	C15—C14—H14A	108.5
O4—C8—C9	126.13 (10)	C13—C14—H14B	108.5
C7—C8—C9	107.96 (9)	C15—C14—H14B	108.5
O2—C9—C10	113.19 (9)	H14A—C14—H14B	107.5
O2—C9—C8	104.70 (9)	C16—C15—C14	118.64 (13)
C10—C9—C8	113.18 (10)	C16—C15—H15A	107.7
O2—C9—C1	105.26 (10)	C14—C15—H15A	107.7
C10—C9—C1	116.99 (9)	C16—C15—H15B	107.7
C8—C9—C1	102.19 (9)	C14—C15—H15B	107.7
C16—C10—C9	109.36 (9)	H15A—C15—H15B	107.1
C16—C10—C11	109.37 (9)	O1—C16—C15	120.34 (12)
C9—C10—C11	114.26 (10)	O1—C16—C10	119.27 (11)
C16—C10—H10	107.9	C15—C16—C10	120.38 (11)
O3—C1—C2—C7	177.60 (13)	O3—C1—C9—O2	−76.24 (15)
C9—C1—C2—C7	3.64 (13)	C2—C1—C9—O2	97.72 (11)
O3—C1—C2—C3	0.9 (2)	O3—C1—C9—C10	50.41 (17)
C9—C1—C2—C3	−173.10 (12)	C2—C1—C9—C10	−135.63 (10)
C7—C2—C3—C4	−2.52 (19)	O3—C1—C9—C8	174.60 (13)
C1—C2—C3—C4	173.93 (12)	C2—C1—C9—C8	−11.44 (12)
C2—C3—C4—C5	0.3 (2)	O2—C9—C10—C16	−174.64 (10)
C3—C4—C5—C6	2.1 (2)	C8—C9—C10—C16	−55.70 (12)
C4—C5—C6—C7	−2.2 (2)	C1—C9—C10—C16	62.72 (13)
C3—C2—C7—C6	2.51 (18)	O2—C9—C10—C11	62.41 (14)
C1—C2—C7—C6	−174.52 (11)	C8—C9—C10—C11	−178.65 (10)
C3—C2—C7—C8	−176.47 (11)	C1—C9—C10—C11	−60.24 (13)
C1—C2—C7—C8	6.50 (14)	C16—C10—C11—C12	83.76 (14)
C5—C6—C7—C2	−0.13 (18)	C9—C10—C11—C12	−153.30 (12)
C5—C6—C7—C8	178.63 (12)	C10—C11—C12—C13	−63.91 (18)
C2—C7—C8—O4	166.80 (13)	C11—C12—C13—C14	62.5 (2)
C6—C7—C8—O4	−12.1 (2)	C12—C13—C14—C15	−79.9 (2)
C2—C7—C8—C9	−14.11 (13)	C13—C14—C15—C16	59.78 (19)
C6—C7—C8—C9	167.02 (12)	C14—C15—C16—O1	−169.58 (14)
O4—C8—C9—O2	84.79 (15)	C14—C15—C16—C10	9.5 (2)
C7—C8—C9—O2	−94.30 (11)	C9—C10—C16—O1	−19.61 (16)
O4—C8—C9—C10	−38.94 (17)	C11—C10—C16—O1	106.21 (14)
C7—C8—C9—C10	141.98 (10)	C9—C10—C16—C15	161.33 (12)
O4—C8—C9—C1	−165.63 (13)	C11—C10—C16—C15	−72.85 (15)
C7—C8—C9—C1	15.28 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4i	0.80 (2)	1.99 (2)	2.7707 (13)	163 (2)
C4—H4···O1ii	0.93	2.48	3.2758 (17)	144
C15—H15B···O3iii	0.97	2.47	3.3998 (19)	160

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2O4i	0.80(2)	1.99(2)	2.7707(13)	163(2)
C4H4O1ii	0.93	2.48	3.2758(17)	144
C15H15BO3iii	0.97	2.47	3.3998(19)	160

Symmetry codes: (i) ; (ii) ; (iii) .