2,7 Di­acetylxanthene

organic papers

o1770

17H14O3 doi:10.1107/S1600536806012050 Acta Cryst.(2006). E62, o1770–o1771

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

2,7-Diacetylxanthene

Li Wu, Ai-Lin Liu , Yang Lu* and Guan-Hua Du

Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xiannong tan street, Beijing 100050, People’s Republic of China

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 296 K

Mean(C–C) = 0.003 A˚

Rfactor = 0.048

wRfactor = 0.128 Data-to-parameter ratio = 8.3

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 5 March 2006 Accepted 3 April 2006

#2006 International Union of Crystallography

All rights reserved

In the crystal structure of the title compound, C17H14O3, the

asymmetric unit comprises one half-molecule; a mirror plane passes through the pyran O atom and thepara-carbon atom.

Comment

The title compound, (I), was synthesized from xanthene and acetyl chloride (Ng & Ng, 1952). Recently, we found that it exhibits anti-xanthine oxidase activity with an inhibition ratio of 71.28% at a concentration of 10 6g ml 1. In the light of this, we have synthesized this compound and determined its structure by X-ray analysis.

Compound (I) crystallizes in the space group Cmc21 with

one half-molecule in the asymmetric unit (Fig. 1). The dihedral angle between the two benzene rings is 11.1 (1)_{, and the}

pyran ring adopts a boat conformation, in which atoms C4, C5, C4iand C5iform the bottom of the boat, O2 the prow and C9 the stern [deviations from the C4/C5/C4i/C5i mean plane = 0.132 (2) and 0.1921 (17) A˚ for O2 and C9, respectively; symmetry code: (i) x,y,z]. Atoms O2 and C9 are located on a mirror plane. No hydrogen-bond interactions are observed between molecules (Fig. 2)

Experimental

The title compound was prepared according to the procedure of Ng & Ng (1952). A single crystal was obtained by slow evaporation of a saturated methanol–hexane(1:1) solution at 283 K.

Figure 1

Crystal data

C17H14O3 Mr= 266.28

Orthorhombic,Cmc21 a= 29.875 (6) A˚ b= 6.0270 (12) A˚ c= 7.2560 (15) A˚ V= 1306.5 (5) A˚3

Z= 4

Dx= 1.354 Mg m 3

MoKradiation

= 0.09 mm 1 T= 296 (1) K Block, pale yellow 0.300.200.10 mm

Data collection

MAC DIP 2030K diffractometer

!scans

Absorption correction: none 1899 measured reflections

785 independent reflections 782 reflections withI> 2(I) Rint= 0.023

max= 27.3

Refinement

Refinement onF2 R[F2> 2(F2)] = 0.048 wR(F2_{) = 0.128} S= 1.11 785 reflections 95 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0667P)2 + 0.4024P]

whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001

max= 0.11 e A˚ 3

min= 0.11 e A˚ 3

Extinction correction:SHELXL97 Extinction coefficient: 0.010 (3)

Table 1

Selected bond and torsion angles (_). C4—O2—C4i

118.6 (2) C5—C9—C5i

112.0 (2)

C4i

—O2—C4—C3 168.35 (15)

C4i

—O2—C4—C5 12.8 (4)

C3—C4—C5—C6 0.2 (3)

O2—C4—C5—C6 179.0 (2)

C3—C4—C5—C9 176.8 (3)

O2—C4—C5—C9 2.0 (3)

C6—C5—C9—C5i

167.84 (16) C4—C5—C9—C5i

15.3 (4)

Symmetry code: (i) x;y;z.

In the absence of significant anomalous scattering, Friedel pairs were merged. Methyl H atoms were constrained to an ideal geometry, with C—H = 0.96 A˚ andUiso(H) = 1.5Ueq(C). All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 A˚ andUiso(H) = 1.2Ueq(C).

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure:

SHELXS97(Sheldrick, 1997); program(s) used to refine structure:

SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII

(Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication:SHELXL97.

The authors acknowledge the financial support of the International Centre for Diffraction Data.

References

Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.

Ng, D.-X. & Ng, P. B.-H. (1952).J. Chem. Soc.pp. 3741–3744.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.

Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

Figure 2

supporting information

sup-1 Acta Cryst. (2006). E62, o1770–o1771

supporting information

Acta Cryst. (2006). E62, o1770–o1771 [https://doi.org/10.1107/S1600536806012050]

2,7-Diacetylxanthene

Li Wu, Ai-Lin Liu, Yang Lu and Guan-Hua Du

2,7-diacetylxanthene

Crystal data C17H14O3

Mr = 266.28

Orthorhombic, Cmc21

Hall symbol: C 2c -2 a = 29.875 (6) Å b = 6.0270 (12) Å c = 7.2560 (15) Å V = 1306.5 (5) Å3

Z = 4

F(000) = 560 Dx = 1.354 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1899 reflections θ = 2.7–27.3°

µ = 0.09 mm−1

T = 296 K

Block, pale yellow 0.30 × 0.20 × 0.10 mm

Data collection MAC DIP 2030K

diffractometer

Radiation source: rotating anode Graphite monochromator

Detector resolution: 0 pixels mm-1

ω scans

1899 measured reflections

785 independent reflections 782 reflections with I > 2σ(I) Rint = 0.023

θmax = 27.3°, θmin = 2.7°

h = −37→38 k = 0→7 l = −9→9

Refinement Refinement on F2

Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.048}

wR(F2_{) = 0.128}

S = 1.11 785 reflections 95 parameters 1 restraint

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(F

o2) + (0.0667P)2 + 0.4024P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.11 e Å−3

Δρmin = −0.11 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4

Extinction coefficient: 0.010 (3)

Special details

Refinement. Refinement of F2 _{against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

O1 0.17114 (5) −0.1266 (3) 0.1160 (5) 0.0832 (8)

O2 0.0000 0.4390 (3) −0.1025 (3) 0.0520 (6)

C1 0.12308 (6) 0.1729 (3) 0.0456 (3) 0.0502 (6)

C2 0.11922 (7) 0.3845 (3) −0.0292 (3) 0.0548 (6)

H2B 0.1447 0.4704 −0.0472 0.066*

C3 0.07776 (7) 0.4680 (3) −0.0768 (3) 0.0520 (6)

H3A 0.0754 0.6091 −0.1277 0.062*

C4 0.03987 (6) 0.3413 (3) −0.0487 (3) 0.0457 (5)

C5 0.04197 (6) 0.1272 (3) 0.0262 (3) 0.0452 (5)

C6 0.08396 (6) 0.0465 (3) 0.0721 (3) 0.0478 (5)

H6A 0.0864 −0.0952 0.1219 0.057*

C7 0.16732 (7) 0.0715 (4) 0.0911 (4) 0.0617 (7)

C8 0.20751 (8) 0.2214 (5) 0.1045 (7) 0.0952 (12)

H8A 0.2337 0.1342 0.1304 0.143*

H8B 0.2030 0.3270 0.2017 0.143*

H8C 0.2115 0.2984 −0.0102 0.143*

C9 0.0000 −0.0111 (5) 0.0458 (5) 0.0518 (7)

H9A 0.0000 −0.0826 0.1656 0.062*

H9B 0.0000 −0.1264 −0.0475 0.062*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

O1 0.0560 (9) 0.0665 (12) 0.1270 (19) 0.0072 (7) 0.0005 (11) 0.0135 (11)

O2 0.0536 (11) 0.0395 (10) 0.0630 (15) 0.000 0.000 0.0093 (9)

C1 0.0451 (9) 0.0520 (10) 0.0535 (13) −0.0023 (7) 0.0033 (8) −0.0054 (10)

C2 0.0536 (11) 0.0511 (11) 0.0597 (13) −0.0108 (8) 0.0074 (10) −0.0019 (10)

C3 0.0607 (11) 0.0400 (9) 0.0554 (12) −0.0053 (8) 0.0045 (9) 0.0024 (8)

C4 0.0493 (10) 0.0395 (9) 0.0484 (12) 0.0005 (6) 0.0028 (8) 0.0001 (9)

C5 0.0481 (10) 0.0379 (9) 0.0495 (12) −0.0022 (6) 0.0023 (7) −0.0009 (8)

C6 0.0467 (9) 0.0435 (9) 0.0533 (12) −0.0003 (7) 0.0031 (8) 0.0003 (8)

C7 0.0476 (10) 0.0641 (13) 0.0736 (15) −0.0015 (9) 0.0054 (10) 0.0010 (12)

C8 0.0486 (12) 0.085 (2) 0.153 (3) −0.0077 (11) −0.0061 (17) −0.003 (2)

C9 0.0435 (13) 0.0400 (12) 0.0720 (19) 0.000 0.000 0.0099 (13)

Geometric parameters (Å, º)

O1—C7 1.213 (3) C5—C6 1.386 (3)

O2—C4 1.385 (2) C5—C9 1.512 (2)

supporting information

sup-3 Acta Cryst. (2006). E62, o1770–o1771

C1—C2 1.391 (3) C7—C8 1.506 (3)

C1—C6 1.408 (2) C8—H8A 0.9600

C1—C7 1.493 (3) C8—H8B 0.9600

C2—C3 1.381 (3) C8—H8C 0.9600

C2—H2B 0.9300 C9—C5i _{1.512 (2)}

C3—C4 1.381 (3) C9—H9A 0.9700

C3—H3A 0.9300 C9—H9B 0.9700

C4—C5 1.401 (3)

C4—O2—C4i _{118.6 (2) C5—C6—H6A 119.1}

C2—C1—C6 118.72 (18) C1—C6—H6A 119.1

C2—C1—C7 122.35 (18) O1—C7—C1 121.3 (2)

C6—C1—C7 118.87 (19) O1—C7—C8 120.4 (2)

C3—C2—C1 120.41 (18) C1—C7—C8 118.3 (2)

C3—C2—H2B 119.8 C7—C8—H8A 109.5

C1—C2—H2B 119.8 C7—C8—H8B 109.5

C2—C3—C4 119.79 (18) H8A—C8—H8B 109.5

C2—C3—H3A 120.1 C7—C8—H8C 109.5

C4—C3—H3A 120.1 H8A—C8—H8C 109.5

C3—C4—O2 115.35 (17) H8B—C8—H8C 109.5

C3—C4—C5 122.01 (17) C5—C9—C5i _{112.0 (2)}

O2—C4—C5 122.64 (16) C5—C9—H9A 109.2

C6—C5—C4 117.19 (16) C5i_{—C9—H9A 109.2}

C6—C5—C9 122.28 (18) C5—C9—H9B 109.2

C4—C5—C9 120.46 (17) C5i_{—C9—H9B 109.2}

C5—C6—C1 121.88 (18) H9A—C9—H9B 107.9

C6—C1—C2—C3 −0.2 (3) C4—C5—C6—C1 0.1 (3)

C7—C1—C2—C3 177.1 (2) C9—C5—C6—C1 177.1 (2)

C1—C2—C3—C4 0.5 (3) C2—C1—C6—C5 −0.1 (3)

C2—C3—C4—O2 −179.4 (2) C7—C1—C6—C5 −177.5 (2)

C2—C3—C4—C5 −0.5 (3) C2—C1—C7—O1 −163.1 (3)

C4i_{—O2—C4—C3 −168.35 (15) C6—C1—C7—O1 14.2 (4)}

C4i_{—O2—C4—C5 12.8 (4) C2—C1—C7—C8 16.5 (4)}

C3—C4—C5—C6 0.2 (3) C6—C1—C7—C8 −166.1 (3)

O2—C4—C5—C6 179.0 (2) C6—C5—C9—C5i _{167.84 (16)}

C3—C4—C5—C9 −176.8 (3) C4—C5—C9—C5i _{−15.3 (4)}

O2—C4—C5—C9 2.0 (3)