9-(2-Hy-droxy-6-oxocyclo-hex-1-en-1-yl)-2,3,4,9-tetra-hydro-1H-xanthen-1-one.

In the xanthene ring system in the title compound, C19H18O4, the 4H-pyran ring has a maximum deviation of 0.110 (2) Å from planarity and the cyclo-hexene ring exhibits a puckered conformation [puckering parameters Q T = 0.452 (3) Å, θ = 57.0 (4) and ϕ = 131.7 (4)°]. The cyclo-hexene ring attached to the xanthene system adopts an envelope conformation, with the middle of the three methylene C atoms as the flap atom. In the crystal, O-H⋯O and C-H⋯O hydrogen bonds form infinite chains of R 1 (2)(6) ring motifs along [100] with the xanthene groups arranged in an alternating zigzag manner.

Related literature

For the bioactivity of xanthene compounds, see: Mohamed et al. (2012a ▶); Mo et al. (2010 ▶) and for their fluorescence properties, see: Menchen et al. (2003 ▶). For similar structures see: Mohamed et al. (2011 ▶, 2012b ▶); Kurbanova et al. (2012 ▶); Abdelhamid et al. (2011 ▶); Reddy et al. (2009 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H18O4

M = 310.33

Orthorhombic,

a = 13.4420 (18) Å

b = 8.0015 (10) Å

c = 14.2416 (18) Å

V = 1531.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 130 K

0.37 × 0.24 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.966, T max = 0.986

13880 measured reflections

1901 independent reflections

1799 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.06

1901 reflections

209 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.18 e Å−3

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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007952/nk2202sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007952/nk2202Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007952/nk2202Isup3.cml

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

C19H18O4	F(000) = 656
Mr = 310.33	Dx = 1.346 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3393 reflections
a = 13.4420 (18) Å	θ = 2.9–27.9°
b = 8.0015 (10) Å	µ = 0.09 mm−1
c = 14.2416 (18) Å	T = 130 K
V = 1531.8 (3) Å3	Prism, pale-yellow
Z = 4	0.37 × 0.24 × 0.15 mm

Bruker SMART APEX diffractometer	1901 independent reflections
Radiation source: sealed tube	1799 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 27.9°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −17→17
Tmin = 0.966, Tmax = 0.986	k = −10→10
13880 measured reflections	l = −18→18

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.111	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.3774P] where P = (Fo2 + 2Fc2)/3
1901 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.28192 (10)	0.69820 (18)	0.43470 (13)	0.0184 (4)
O2	−0.06046 (11)	0.61746 (18)	0.43776 (14)	0.0212 (4)
O3	0.32497 (11)	0.31450 (18)	0.43000 (13)	0.0201 (4)
O4	0.06177 (15)	0.4417 (3)	0.63635 (14)	0.0332 (6)
C1	0.11167 (14)	0.6473 (2)	0.44797 (16)	0.0146 (5)
C2	0.19662 (15)	0.7556 (2)	0.44266 (16)	0.0148 (5)
C3	0.18243 (15)	0.9436 (2)	0.4447 (2)	0.0213 (6)
C4	0.08584 (18)	0.9945 (3)	0.4923 (2)	0.0287 (7)
C5	−0.00064 (16)	0.9004 (3)	0.4487 (2)	0.0282 (7)
C6	0.01837 (15)	0.7154 (2)	0.44477 (17)	0.0170 (5)
C7	0.12663 (14)	0.4583 (2)	0.44760 (16)	0.0143 (5)
C8	0.16996 (17)	0.3960 (3)	0.35574 (16)	0.0169 (6)
C9	0.1140 (2)	0.4019 (3)	0.27230 (18)	0.0245 (7)
C10	0.1531 (2)	0.3453 (3)	0.18896 (19)	0.0309 (8)
C11	0.2489 (3)	0.2819 (3)	0.18615 (19)	0.0337 (8)
C12	0.3059 (2)	0.2744 (3)	0.26740 (19)	0.0273 (7)
C13	0.26539 (18)	0.3314 (3)	0.35123 (17)	0.0189 (6)
C14	0.28205 (18)	0.3342 (3)	0.51564 (16)	0.0175 (6)
C15	0.35058 (18)	0.2726 (3)	0.59122 (19)	0.0247 (7)
C16	0.3183 (2)	0.3350 (3)	0.6870 (2)	0.0312 (8)
C17	0.2073 (2)	0.3126 (4)	0.70056 (19)	0.0329 (9)
C18	0.14584 (19)	0.3913 (3)	0.62272 (17)	0.0226 (6)
C19	0.18972 (17)	0.3968 (3)	0.52852 (15)	0.0159 (6)
H2	−0.11220	0.67370	0.44770	0.0320*
H3A	0.18270	0.98680	0.37960	0.0260*
H3B	0.23900	0.99530	0.47850	0.0260*
H4A	0.08960	0.96920	0.56020	0.0340*
H4B	0.07550	1.11630	0.48490	0.0340*
H5A	−0.06160	0.92160	0.48590	0.0340*
H5B	−0.01220	0.94270	0.38430	0.0340*
H7A	0.05940	0.40600	0.45460	0.0170*
H9A	0.04840	0.44570	0.27360	0.0290*
H10A	0.11430	0.34970	0.13320	0.0370*
H11A	0.27580	0.24340	0.12840	0.0400*
H12A	0.37160	0.23090	0.26570	0.0330*
H15A	0.41910	0.31150	0.57810	0.0300*
H15B	0.35100	0.14880	0.59120	0.0300*
H16A	0.35440	0.27270	0.73640	0.0370*
H16B	0.33550	0.45480	0.69320	0.0370*
H17A	0.18780	0.36300	0.76130	0.0390*
H17B	0.19210	0.19170	0.70360	0.0390*

	U11	U22	U33	U12	U13	U23
O1	0.0111 (6)	0.0182 (6)	0.0260 (8)	−0.0017 (5)	0.0003 (7)	0.0003 (7)
O2	0.0101 (7)	0.0176 (7)	0.0358 (9)	0.0000 (5)	−0.0006 (8)	−0.0019 (8)
O3	0.0144 (7)	0.0194 (7)	0.0265 (9)	0.0032 (5)	0.0007 (7)	0.0003 (7)
O4	0.0272 (10)	0.0447 (11)	0.0278 (10)	0.0020 (8)	0.0065 (8)	−0.0008 (8)
C1	0.0129 (9)	0.0127 (8)	0.0181 (10)	−0.0003 (7)	−0.0004 (8)	−0.0004 (8)
C2	0.0138 (9)	0.0145 (8)	0.0160 (9)	−0.0005 (7)	−0.0019 (8)	0.0003 (9)
C3	0.0165 (9)	0.0131 (8)	0.0343 (12)	−0.0026 (7)	0.0002 (10)	0.0005 (10)
C4	0.0197 (11)	0.0170 (10)	0.0493 (16)	−0.0001 (9)	0.0003 (11)	−0.0086 (11)
C5	0.0158 (10)	0.0142 (9)	0.0547 (17)	0.0031 (7)	−0.0026 (12)	−0.0034 (12)
C6	0.0153 (9)	0.0142 (8)	0.0214 (10)	0.0000 (7)	−0.0018 (9)	−0.0018 (9)
C7	0.0119 (8)	0.0119 (7)	0.0192 (10)	−0.0011 (7)	−0.0014 (8)	0.0009 (8)
C8	0.0220 (11)	0.0110 (10)	0.0177 (10)	−0.0013 (8)	−0.0006 (9)	−0.0005 (8)
C9	0.0336 (13)	0.0180 (11)	0.0218 (11)	−0.0016 (10)	−0.0075 (10)	0.0001 (9)
C10	0.0510 (17)	0.0207 (11)	0.0210 (12)	−0.0021 (11)	−0.0086 (12)	−0.0012 (10)
C11	0.0585 (19)	0.0233 (12)	0.0192 (12)	0.0008 (12)	0.0094 (12)	−0.0019 (10)
C12	0.0342 (14)	0.0179 (11)	0.0297 (13)	0.0035 (10)	0.0118 (11)	0.0002 (10)
C13	0.0235 (11)	0.0133 (10)	0.0198 (10)	−0.0012 (8)	0.0033 (9)	0.0005 (8)
C14	0.0198 (10)	0.0121 (9)	0.0207 (11)	−0.0017 (8)	−0.0039 (9)	0.0018 (8)
C15	0.0230 (12)	0.0209 (11)	0.0303 (13)	0.0016 (9)	−0.0069 (10)	0.0052 (10)
C16	0.0371 (15)	0.0303 (13)	0.0262 (13)	0.0039 (11)	−0.0113 (11)	0.0021 (11)
C17	0.0446 (17)	0.0358 (15)	0.0184 (12)	−0.0025 (12)	−0.0003 (11)	0.0070 (11)
C18	0.0266 (12)	0.0210 (10)	0.0201 (11)	−0.0048 (9)	0.0027 (10)	−0.0017 (9)
C19	0.0198 (10)	0.0119 (9)	0.0159 (10)	−0.0019 (8)	−0.0016 (8)	0.0013 (8)

O1—C2	1.240 (2)	C14—C15	1.500 (3)
O2—C6	1.322 (2)	C15—C16	1.516 (4)
O3—C13	1.385 (3)	C16—C17	1.515 (4)
O3—C14	1.358 (3)	C17—C18	1.519 (4)
O4—C18	1.216 (3)	C18—C19	1.466 (3)
O2—H2	0.8400	C3—H3A	0.9900
C1—C6	1.368 (3)	C3—H3B	0.9900
C1—C7	1.526 (2)	C4—H4A	0.9900
C1—C2	1.436 (3)	C4—H4B	0.9900
C2—C3	1.517 (2)	C5—H5A	0.9900
C3—C4	1.520 (3)	C5—H5B	0.9900
C4—C5	1.518 (3)	C7—H7A	1.0000
C5—C6	1.503 (3)	C9—H9A	0.9500
C7—C19	1.513 (3)	C10—H10A	0.9500
C7—C8	1.516 (3)	C11—H11A	0.9500
C8—C9	1.407 (3)	C12—H12A	0.9500
C8—C13	1.385 (3)	C15—H15A	0.9900
C9—C10	1.375 (4)	C15—H15B	0.9900
C10—C11	1.385 (5)	C16—H16A	0.9900
C11—C12	1.389 (4)	C16—H16B	0.9900
C12—C13	1.389 (4)	C17—H17A	0.9900
C14—C19	1.351 (3)	C17—H17B	0.9900
C13—O3—C14	118.06 (18)	C2—C3—H3B	109.00
C6—O2—H2	109.00	C4—C3—H3A	109.00
C2—C1—C7	119.56 (16)	C4—C3—H3B	109.00
C6—C1—C7	121.03 (16)	H3A—C3—H3B	108.00
C2—C1—C6	119.14 (15)	C3—C4—H4A	110.00
O1—C2—C3	119.03 (17)	C3—C4—H4B	110.00
C1—C2—C3	119.85 (17)	C5—C4—H4A	110.00
O1—C2—C1	121.11 (15)	C5—C4—H4B	110.00
C2—C3—C4	112.44 (17)	H4A—C4—H4B	108.00
C3—C4—C5	109.8 (2)	C4—C5—H5A	109.00
C4—C5—C6	111.93 (19)	C4—C5—H5B	109.00
O2—C6—C5	116.77 (17)	C6—C5—H5A	109.00
C1—C6—C5	123.15 (17)	C6—C5—H5B	109.00
O2—C6—C1	120.08 (15)	H5A—C5—H5B	108.00
C1—C7—C19	113.18 (17)	C1—C7—H7A	107.00
C8—C7—C19	109.57 (17)	C8—C7—H7A	107.00
C1—C7—C8	112.30 (18)	C19—C7—H7A	107.00
C7—C8—C13	121.2 (2)	C8—C9—H9A	120.00
C9—C8—C13	118.0 (2)	C10—C9—H9A	120.00
C7—C8—C9	120.8 (2)	C9—C10—H10A	120.00
C8—C9—C10	120.9 (2)	C11—C10—H10A	120.00
C9—C10—C11	120.1 (3)	C10—C11—H11A	120.00
C10—C11—C12	120.3 (3)	C12—C11—H11A	120.00
C11—C12—C13	119.0 (3)	C11—C12—H12A	121.00
O3—C13—C12	115.9 (2)	C13—C12—H12A	120.00
C8—C13—C12	121.7 (2)	C14—C15—H15A	109.00
O3—C13—C8	122.3 (2)	C14—C15—H15B	109.00
O3—C14—C15	110.2 (2)	C16—C15—H15A	109.00
O3—C14—C19	123.7 (2)	C16—C15—H15B	109.00
C15—C14—C19	126.1 (2)	H15A—C15—H15B	108.00
C14—C15—C16	111.2 (2)	C15—C16—H16A	109.00
C15—C16—C17	111.0 (2)	C15—C16—H16B	109.00
C16—C17—C18	113.2 (2)	C17—C16—H16A	109.00
O4—C18—C19	120.7 (2)	C17—C16—H16B	109.00
C17—C18—C19	117.5 (2)	H16A—C16—H16B	108.00
O4—C18—C17	121.8 (2)	C16—C17—H17A	109.00
C7—C19—C18	118.8 (2)	C16—C17—H17B	109.00
C14—C19—C18	118.9 (2)	C18—C17—H17A	109.00
C7—C19—C14	122.2 (2)	C18—C17—H17B	109.00
C2—C3—H3A	109.00	H17A—C17—H17B	108.00
C14—O3—C13—C8	11.8 (3)	C8—C7—C19—C14	15.1 (3)
C14—O3—C13—C12	−166.1 (2)	C8—C7—C19—C18	−159.4 (2)
C13—O3—C14—C15	166.70 (19)	C7—C8—C9—C10	−179.9 (2)
C13—O3—C14—C19	−11.8 (3)	C13—C8—C9—C10	−0.1 (4)
C6—C1—C2—O1	−171.8 (2)	C7—C8—C13—O3	2.3 (3)
C6—C1—C2—C3	6.9 (3)	C7—C8—C13—C12	−179.8 (2)
C7—C1—C2—O1	2.4 (3)	C9—C8—C13—O3	−177.5 (2)
C7—C1—C2—C3	−178.9 (2)	C9—C8—C13—C12	0.3 (4)
C2—C1—C6—O2	171.6 (2)	C8—C9—C10—C11	−0.2 (4)
C2—C1—C6—C5	−8.3 (4)	C9—C10—C11—C12	0.3 (4)
C7—C1—C6—O2	−2.5 (4)	C10—C11—C12—C13	0.0 (4)
C7—C1—C6—C5	177.6 (2)	C11—C12—C13—O3	177.7 (2)
C2—C1—C7—C8	−65.0 (3)	C11—C12—C13—C8	−0.3 (4)
C2—C1—C7—C19	59.7 (3)	O3—C14—C15—C16	164.41 (19)
C6—C1—C7—C8	109.0 (2)	C19—C14—C15—C16	−17.2 (3)
C6—C1—C7—C19	−126.3 (2)	O3—C14—C19—C7	−2.7 (4)
O1—C2—C3—C4	−157.1 (2)	O3—C14—C19—C18	171.8 (2)
C1—C2—C3—C4	24.2 (3)	C15—C14—C19—C7	179.1 (2)
C2—C3—C4—C5	−52.2 (3)	C15—C14—C19—C18	−6.4 (4)
C3—C4—C5—C6	50.8 (3)	C14—C15—C16—C17	46.1 (3)
C4—C5—C6—O2	158.5 (2)	C15—C16—C17—C18	−54.0 (3)
C4—C5—C6—C1	−21.6 (3)	C16—C17—C18—O4	−151.9 (3)
C1—C7—C8—C9	−68.2 (3)	C16—C17—C18—C19	31.2 (3)
C1—C7—C8—C13	111.9 (2)	O4—C18—C19—C7	−3.0 (4)
C19—C7—C8—C9	165.1 (2)	O4—C18—C19—C14	−177.7 (2)
C19—C7—C8—C13	−14.7 (3)	C17—C18—C19—C7	173.9 (2)
C1—C7—C19—C14	−111.1 (2)	C17—C18—C19—C14	−0.8 (3)
C1—C7—C19—C18	74.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.84	1.76	2.582 (2)	164
C5—H5A···O1i	0.99	2.42	3.034 (3)	119
C7—H7A···O2	1.00	2.35	2.822 (2)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.84	1.76	2.582 (2)	164
C5—H5A⋯O1i	0.99	2.42	3.034 (3)	119

Symmetry code: (i) .