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ISSN: 2056-9890

3-(4-Meth­oxy­phen­yl)-1H-isochromen-1-one

aSchool of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and cOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139-Samsun, Turkey
*Correspondence e-mail: nawaz_f@yahoo.co.in

(Received 28 November 2008; accepted 10 December 2008; online 17 December 2008)

The asymmetric unit of the title compound, C16H12O3, contains two crystallographically independent mol­ecules. The isochromene ring system is planar (maximum deviation 0.024 Å) and is oriented at dihedral angles of 2.63 (3) and 0.79 (3)° with respect to the methoxy­benzene rings in the two independent mol­ecules.

Related literature

For general background, see: Barry (1964[Barry, R. D. (1964). Chem. Rev. 64, 229-260.]); Hill (1986[Hill, R. A. (1986). Fortschr. Chem. Org. Naturst. 49, 1-78.]); Canendo et al. (1997[Canendo, L. M., Puents, J. L. F. & Baz, J. P. (1997). J. Antibiot. 50, 175-176.]); Whyte et al. (1996[Whyte, A. C., Gloer, J. B., Scott, J. A. & Malloch, D. (1996). J. Nat. Prod. 59, 765-769.]). For related structures, see: Abid et al. (2006[Abid, O., Rama, N. H., Qadeer, G., Khan, G. S. & Lu, X.-M. (2006). Acta Cryst. E62, o2895-o2896.], 2008[Abid, O.-U.-R., Qadeer, G., Rama, N. H., Ruzicka, A. & Padelkova, Z. (2008). Acta Cryst. E64, o2018.]); Hathwar et al. (2007[Hathwar, V. R., Manivel, P., Nawaz Khan, F. & Guru Row, T. N. (2007). Acta Cryst. E63, o3707.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12O3

  • Mr = 252.26

  • Monoclinic, P 21 /c

  • a = 15.5949 (15) Å

  • b = 11.8464 (11) Å

  • c = 15.1824 (14) Å

  • β = 117.838 (2)°

  • V = 2480.2 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 290 (2) K

  • 0.28 × 0.14 × 0.08 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.984

  • 18262 measured reflections

  • 4616 independent reflections

  • 2795 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.109

  • S = 1.00

  • 4616 reflections

  • 345 parameters

  • All H-atom parameters refined

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and CAMERON (Watkin et al., 1993[Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

Isochromenones are structurally related to the chromenones, (Hill, 1986). They have a wide range of biological activities (Hill, 1986; Canendo et al., 1997; Whyte et al., 1996). Isocoumarins (Barry, 1964) are also useful intermediates in the synthesis of a variety of important compounds including some carbocyclic and heterocyclic compounds. In view of their natural occurrence, biological activities and utility as synthetic intermediates, we have synthesized the title compound, and reported herein its crystal structure.

The asymmetric unit of the title compound contains two crystallographically independent molecules of similar geometry. The dihedral angels between the isochromene ring system and the methoxybenzene rings amount to 2.63 (3) and 0.79 (3) ° in the two crystallographically independent molecules

Related literature top

For general background, see: Barry (1964); Hill (1986); Canendo et al. (1997); Whyte et al. (1996). For related structures, see: Abid et al. (2006, 2008); Hathwar et al. (2007).

Experimental top

Homophthalic acid (1.3 g, 7.2 mmol) was added to p-methoxybenzoyl chloride (24.8 mmol) and was refluxed for 4 h at 473 K with stirring. The reaction mixture was extracted with ethyl acetate (3 times 100 ml), and an aqueous solution of sodium carbonate (5%, 200 ml) was added to remove the unreacted homophthalic acid. The organic layer was separated, concentrated and chromatographed on silica gel using petroleum ether (313–353 K fractions) as eluent to afford the title compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

Refinement top

All H atoms were positioned with idealized geometry and were refined using a riding model with C-H = 0.96 Å for CH3 and 0.93 Å for aromatic H atoms. The displacement parameters of the H atoms were constrained as Uiso(H) = 1.2Ueq (1.5Ueq for methyl) of the carrier atom.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. : Crystal structure of the title complex, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
3-(4-Methoxyphenyl)-1H-isochromen-1-one top
Crystal data top
C16H12O3F(000) = 1056
Mr = 252.26Dx = 1.351 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8668 reflections
a = 15.5949 (15) Åθ = 1.5–25.5°
b = 11.8464 (11) ŵ = 0.09 mm1
c = 15.1824 (14) ÅT = 290 K
β = 117.838 (2)°Block, colourless
V = 2480.2 (4) Å30.28 × 0.14 × 0.08 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
4616 independent reflections
Radiation source: fine-focus sealed tube2795 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1818
Tmin = 0.974, Tmax = 0.984k = 1314
18262 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109All H-atom parameters refined
S = 1.00 w = 1/[σ2(Fo2) + (0.0567P)2]
where P = (Fo2 + 2Fc2)/3
4616 reflections(Δ/σ)max = 0.001
345 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C16H12O3V = 2480.2 (4) Å3
Mr = 252.26Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.5949 (15) ŵ = 0.09 mm1
b = 11.8464 (11) ÅT = 290 K
c = 15.1824 (14) Å0.28 × 0.14 × 0.08 mm
β = 117.838 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4616 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2795 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.984Rint = 0.038
18262 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.109All H-atom parameters refined
S = 1.00Δρmax = 0.15 e Å3
4616 reflectionsΔρmin = 0.15 e Å3
345 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.46573 (12)0.71997 (11)1.12417 (10)0.0894 (5)
O20.41915 (8)0.88630 (10)1.05390 (8)0.0602 (3)
O30.35416 (9)1.40912 (10)1.06979 (10)0.0762 (4)
O40.03964 (12)0.71696 (11)0.15948 (11)0.0912 (5)
O50.08196 (8)0.88474 (10)0.13156 (8)0.0595 (3)
O60.13583 (9)1.40934 (10)0.20493 (9)0.0667 (4)
C10.43111 (14)0.77173 (16)1.04693 (14)0.0606 (5)
C20.38013 (11)0.95680 (14)0.97170 (12)0.0470 (4)
C30.35328 (11)0.91498 (14)0.88124 (12)0.0496 (4)
H30.32760.96340.82670.060*
C40.33679 (13)0.75059 (16)0.77199 (13)0.0600 (5)
H40.31210.79670.71590.072*
C50.34738 (13)0.63695 (17)0.76232 (14)0.0667 (5)
H50.33050.60690.69980.080*
C60.38271 (13)0.56691 (17)0.84417 (15)0.0690 (5)
H60.38850.48990.83640.083*
C70.40934 (13)0.61035 (16)0.93675 (14)0.0646 (5)
H70.43320.56300.99200.077*
C80.40056 (12)0.72591 (15)0.94798 (12)0.0503 (4)
C90.36294 (11)0.79755 (14)0.86563 (12)0.0475 (4)
C100.37489 (11)1.07382 (14)1.00008 (12)0.0467 (4)
C110.40524 (12)1.10565 (15)1.09812 (12)0.0551 (5)
H110.42971.05081.14760.066*
C120.40041 (13)1.21545 (16)1.12477 (13)0.0581 (5)
H120.42211.23401.19130.070*
C130.36364 (13)1.29749 (15)1.05313 (14)0.0552 (5)
C140.33210 (13)1.26874 (16)0.95395 (14)0.0629 (5)
H140.30671.32380.90470.076*
C150.33854 (13)1.15925 (15)0.92883 (13)0.0593 (5)
H150.31811.14140.86230.071*
C160.38761 (16)1.44487 (18)1.16989 (16)0.0882 (7)
H16A0.34741.41261.19560.132*
H16B0.38461.52571.17200.132*
H16C0.45341.42051.20960.132*
C170.07336 (13)0.77001 (16)0.11542 (13)0.0607 (5)
C180.11848 (11)0.95659 (14)0.08575 (11)0.0473 (4)
C190.14586 (11)0.91583 (14)0.02099 (12)0.0507 (4)
H190.16910.96530.01050.061*
C200.16909 (13)0.75191 (15)0.06827 (14)0.0608 (5)
H200.19140.79930.10200.073*
C210.16469 (14)0.63793 (17)0.08482 (14)0.0690 (5)
H210.18460.60870.12920.083*
C220.13085 (14)0.56579 (17)0.03610 (14)0.0713 (6)
H220.12810.48840.04760.086*
C230.10135 (13)0.60905 (16)0.02928 (14)0.0664 (5)
H230.07850.56090.06200.080*
C240.10552 (12)0.72472 (15)0.04675 (12)0.0510 (4)
C250.14046 (11)0.79797 (14)0.00148 (12)0.0477 (4)
C260.12307 (11)1.07354 (14)0.11878 (11)0.0471 (4)
C270.09425 (12)1.10360 (15)0.18924 (12)0.0575 (5)
H270.07231.04760.21670.069*
C280.09700 (13)1.21374 (15)0.22010 (13)0.0584 (5)
H280.07721.23120.26750.070*
C290.12929 (12)1.29732 (15)0.18019 (13)0.0517 (5)
C300.15888 (13)1.26986 (15)0.10993 (14)0.0621 (5)
H300.18111.32610.08290.074*
C310.15544 (13)1.16016 (15)0.08009 (13)0.0595 (5)
H310.17531.14320.03260.071*
C320.09712 (14)1.44297 (16)0.26951 (14)0.0770 (6)
H32A0.03171.41630.24340.115*
H32B0.09791.52380.27410.115*
H32C0.13581.41140.33450.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1390 (14)0.0681 (9)0.0507 (8)0.0230 (9)0.0355 (9)0.0148 (7)
O20.0798 (9)0.0542 (8)0.0436 (7)0.0102 (6)0.0262 (6)0.0041 (6)
O30.0977 (11)0.0546 (9)0.0764 (10)0.0029 (7)0.0407 (8)0.0108 (7)
O40.1466 (14)0.0660 (9)0.1082 (11)0.0176 (9)0.0991 (11)0.0002 (8)
O50.0785 (9)0.0537 (8)0.0633 (8)0.0091 (6)0.0473 (7)0.0027 (6)
O60.0808 (9)0.0559 (9)0.0723 (9)0.0028 (7)0.0431 (7)0.0091 (7)
C10.0737 (14)0.0577 (13)0.0510 (12)0.0102 (10)0.0295 (11)0.0063 (10)
C20.0468 (10)0.0532 (12)0.0422 (10)0.0010 (8)0.0216 (8)0.0069 (9)
C30.0550 (11)0.0513 (12)0.0421 (10)0.0013 (8)0.0222 (9)0.0070 (8)
C40.0612 (13)0.0649 (14)0.0481 (11)0.0035 (10)0.0207 (10)0.0031 (9)
C50.0642 (13)0.0718 (15)0.0568 (13)0.0066 (11)0.0220 (11)0.0176 (11)
C60.0734 (14)0.0573 (13)0.0729 (14)0.0018 (10)0.0313 (12)0.0088 (11)
C70.0747 (14)0.0571 (14)0.0642 (13)0.0108 (10)0.0343 (11)0.0048 (10)
C80.0505 (11)0.0533 (12)0.0491 (11)0.0024 (9)0.0249 (9)0.0002 (9)
C90.0424 (10)0.0560 (12)0.0446 (11)0.0041 (8)0.0208 (9)0.0018 (9)
C100.0425 (10)0.0514 (11)0.0458 (10)0.0009 (8)0.0203 (8)0.0010 (9)
C110.0613 (12)0.0582 (13)0.0469 (11)0.0034 (9)0.0261 (9)0.0023 (9)
C120.0663 (13)0.0611 (13)0.0477 (11)0.0006 (10)0.0271 (10)0.0052 (10)
C130.0554 (12)0.0506 (13)0.0622 (13)0.0029 (9)0.0296 (10)0.0074 (10)
C140.0723 (14)0.0546 (13)0.0527 (12)0.0058 (10)0.0215 (10)0.0072 (10)
C150.0704 (13)0.0562 (13)0.0458 (11)0.0014 (10)0.0226 (10)0.0015 (9)
C160.1071 (18)0.0744 (16)0.0891 (16)0.0108 (13)0.0508 (14)0.0317 (13)
C170.0746 (14)0.0555 (13)0.0621 (12)0.0061 (10)0.0404 (11)0.0017 (10)
C180.0462 (10)0.0534 (12)0.0451 (10)0.0041 (8)0.0236 (9)0.0041 (8)
C190.0535 (11)0.0532 (12)0.0514 (10)0.0030 (8)0.0296 (9)0.0036 (9)
C200.0659 (13)0.0609 (14)0.0676 (12)0.0032 (10)0.0413 (11)0.0041 (10)
C210.0744 (14)0.0692 (14)0.0755 (14)0.0024 (11)0.0451 (12)0.0095 (11)
C220.0824 (15)0.0551 (13)0.0783 (14)0.0029 (10)0.0391 (12)0.0053 (11)
C230.0775 (14)0.0581 (14)0.0695 (13)0.0065 (10)0.0393 (11)0.0005 (10)
C240.0512 (11)0.0520 (12)0.0501 (10)0.0006 (9)0.0237 (9)0.0003 (9)
C250.0428 (10)0.0552 (12)0.0444 (10)0.0001 (8)0.0198 (9)0.0005 (9)
C260.0442 (10)0.0524 (11)0.0453 (10)0.0005 (8)0.0213 (8)0.0017 (8)
C270.0646 (12)0.0618 (13)0.0562 (11)0.0057 (9)0.0365 (10)0.0009 (9)
C280.0684 (13)0.0622 (13)0.0551 (11)0.0019 (10)0.0377 (10)0.0064 (10)
C290.0519 (11)0.0509 (12)0.0523 (11)0.0009 (9)0.0243 (9)0.0022 (9)
C300.0728 (14)0.0543 (12)0.0749 (13)0.0098 (10)0.0478 (12)0.0024 (10)
C310.0731 (13)0.0595 (13)0.0634 (12)0.0060 (10)0.0465 (11)0.0055 (10)
C320.0862 (15)0.0708 (15)0.0819 (14)0.0036 (11)0.0459 (13)0.0175 (11)
Geometric parameters (Å, º) top
O1—C11.2048 (19)C14—H140.9300
O2—C11.381 (2)C15—H150.9300
O2—C21.3842 (18)C16—H16A0.9600
O3—C131.3672 (19)C16—H16B0.9600
O3—C161.422 (2)C16—H16C0.9600
O4—C171.2032 (19)C17—C241.454 (2)
O5—C171.3765 (19)C18—C191.332 (2)
O5—C181.3794 (17)C18—C261.464 (2)
O6—C291.3700 (18)C19—C251.431 (2)
O6—C321.4272 (19)C19—H190.9300
C1—C81.453 (2)C20—C211.369 (2)
C2—C31.330 (2)C20—C251.396 (2)
C2—C101.465 (2)C20—H200.9300
C3—C91.431 (2)C21—C221.386 (3)
C3—H30.9300C21—H210.9300
C4—C51.373 (2)C22—C231.373 (2)
C4—C91.398 (2)C22—H220.9300
C4—H40.9300C23—C241.391 (2)
C5—C61.377 (2)C23—H230.9300
C5—H50.9300C24—C251.400 (2)
C6—C71.367 (2)C26—C271.387 (2)
C6—H60.9300C26—C311.389 (2)
C7—C81.394 (2)C27—C281.380 (2)
C7—H70.9300C27—H270.9300
C8—C91.394 (2)C28—C291.373 (2)
C10—C111.387 (2)C28—H280.9300
C10—C151.394 (2)C29—C301.384 (2)
C11—C121.375 (2)C30—C311.369 (2)
C11—H110.9300C30—H300.9300
C12—C131.369 (2)C31—H310.9300
C12—H120.9300C32—H32A0.9600
C13—C141.391 (2)C32—H32B0.9600
C14—C151.369 (2)C32—H32C0.9600
C1—O2—C2122.83 (14)H16A—C16—H16C109.5
C13—O3—C16117.94 (15)H16B—C16—H16C109.5
C17—O5—C18123.25 (13)O4—C17—O5116.63 (16)
C29—O6—C32117.23 (14)O4—C17—C24126.34 (18)
O1—C1—O2116.16 (16)O5—C17—C24117.03 (15)
O1—C1—C8126.72 (19)C19—C18—O5119.92 (15)
O2—C1—C8117.12 (16)C19—C18—C26127.93 (15)
C3—C2—O2120.00 (16)O5—C18—C26112.14 (13)
C3—C2—C10128.46 (16)C18—C19—C25121.77 (15)
O2—C2—C10111.54 (14)C18—C19—H19119.1
C2—C3—C9121.76 (16)C25—C19—H19119.1
C2—C3—H3119.1C21—C20—C25120.88 (17)
C9—C3—H3119.1C21—C20—H20119.6
C5—C4—C9120.42 (17)C25—C20—H20119.6
C5—C4—H4119.8C20—C21—C22120.60 (18)
C9—C4—H4119.8C20—C21—H21119.7
C4—C5—C6120.79 (18)C22—C21—H21119.7
C4—C5—H5119.6C23—C22—C21119.68 (19)
C6—C5—H5119.6C23—C22—H22120.2
C7—C6—C5120.17 (19)C21—C22—H22120.2
C7—C6—H6119.9C22—C23—C24120.24 (18)
C5—C6—H6119.9C22—C23—H23119.9
C6—C7—C8119.70 (18)C24—C23—H23119.9
C6—C7—H7120.2C23—C24—C25120.39 (16)
C8—C7—H7120.2C23—C24—C17119.93 (16)
C9—C8—C7120.83 (16)C25—C24—C17119.69 (17)
C9—C8—C1119.83 (17)C20—C25—C24118.20 (16)
C7—C8—C1119.34 (17)C20—C25—C19123.49 (15)
C8—C9—C4118.06 (16)C24—C25—C19118.31 (15)
C8—C9—C3118.44 (15)C27—C26—C31116.70 (16)
C4—C9—C3123.50 (16)C27—C26—C18121.72 (15)
C11—C10—C15116.53 (16)C31—C26—C18121.58 (14)
C11—C10—C2122.33 (16)C28—C27—C26122.33 (16)
C15—C10—C2121.13 (15)C28—C27—H27118.8
C12—C11—C10122.34 (17)C26—C27—H27118.8
C12—C11—H11118.8C29—C28—C27119.43 (16)
C10—C11—H11118.8C29—C28—H28120.3
C13—C12—C11119.88 (17)C27—C28—H28120.3
C13—C12—H12120.1O6—C29—C28124.97 (16)
C11—C12—H12120.1O6—C29—C30115.46 (16)
O3—C13—C12125.53 (17)C28—C29—C30119.57 (17)
O3—C13—C14115.03 (17)C31—C30—C29120.16 (17)
C12—C13—C14119.44 (17)C31—C30—H30119.9
C15—C14—C13119.93 (17)C29—C30—H30119.9
C15—C14—H14120.0C30—C31—C26121.81 (16)
C13—C14—H14120.0C30—C31—H31119.1
C14—C15—C10121.87 (16)C26—C31—H31119.1
C14—C15—H15119.1O6—C32—H32A109.5
C10—C15—H15119.1O6—C32—H32B109.5
O3—C16—H16A109.5H32A—C32—H32B109.5
O3—C16—H16B109.5O6—C32—H32C109.5
H16A—C16—H16B109.5H32A—C32—H32C109.5
O3—C16—H16C109.5H32B—C32—H32C109.5
C2—O2—C1—O1179.82 (16)C18—O5—C17—O4179.43 (17)
C2—O2—C1—C80.1 (2)C18—O5—C17—C240.4 (2)
C1—O2—C2—C30.7 (2)C17—O5—C18—C191.2 (2)
C1—O2—C2—C10179.49 (14)C17—O5—C18—C26177.86 (14)
O2—C2—C3—C90.4 (2)O5—C18—C19—C251.3 (2)
C10—C2—C3—C9179.86 (14)C26—C18—C19—C25177.58 (15)
C9—C4—C5—C60.8 (3)C25—C20—C21—C220.6 (3)
C4—C5—C6—C71.1 (3)C20—C21—C22—C230.1 (3)
C5—C6—C7—C80.0 (3)C21—C22—C23—C240.1 (3)
C6—C7—C8—C91.4 (3)C22—C23—C24—C250.5 (3)
C6—C7—C8—C1178.60 (17)C22—C23—C24—C17179.46 (17)
O1—C1—C8—C9179.05 (18)O4—C17—C24—C232.0 (3)
O2—C1—C8—C91.3 (2)O5—C17—C24—C23178.20 (15)
O1—C1—C8—C71.0 (3)O4—C17—C24—C25177.94 (19)
O2—C1—C8—C7178.74 (15)O5—C17—C24—C251.9 (2)
C7—C8—C9—C41.7 (2)C21—C20—C25—C241.1 (3)
C1—C8—C9—C4178.31 (15)C21—C20—C25—C19178.23 (16)
C7—C8—C9—C3178.43 (14)C23—C24—C25—C201.1 (2)
C1—C8—C9—C31.6 (2)C17—C24—C25—C20178.86 (15)
C5—C4—C9—C80.6 (2)C23—C24—C25—C19178.30 (15)
C5—C4—C9—C3179.54 (16)C17—C24—C25—C191.8 (2)
C2—C3—C9—C80.7 (2)C18—C19—C25—C20179.51 (16)
C2—C3—C9—C4179.12 (16)C18—C19—C25—C240.2 (2)
C3—C2—C10—C11179.61 (16)C19—C18—C26—C27178.18 (17)
O2—C2—C10—C110.6 (2)O5—C18—C26—C270.8 (2)
C3—C2—C10—C150.3 (3)C19—C18—C26—C312.6 (3)
O2—C2—C10—C15179.50 (14)O5—C18—C26—C31178.40 (15)
C15—C10—C11—C120.2 (2)C31—C26—C27—C280.1 (3)
C2—C10—C11—C12179.95 (15)C18—C26—C27—C28179.13 (15)
C10—C11—C12—C130.7 (3)C26—C27—C28—C290.0 (3)
C16—O3—C13—C122.0 (3)C32—O6—C29—C286.6 (2)
C16—O3—C13—C14178.23 (17)C32—O6—C29—C30173.92 (16)
C11—C12—C13—O3179.38 (15)C27—C28—C29—O6179.69 (15)
C11—C12—C13—C140.4 (3)C27—C28—C29—C300.2 (3)
O3—C13—C14—C15179.79 (16)O6—C29—C30—C31179.88 (15)
C12—C13—C14—C150.4 (3)C28—C29—C30—C310.4 (3)
C13—C14—C15—C100.9 (3)C29—C30—C31—C260.3 (3)
C11—C10—C15—C140.7 (3)C27—C26—C31—C300.0 (3)
C2—C10—C15—C14179.22 (15)C18—C26—C31—C30179.28 (16)

Experimental details

Crystal data
Chemical formulaC16H12O3
Mr252.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)290
a, b, c (Å)15.5949 (15), 11.8464 (11), 15.1824 (14)
β (°) 117.838 (2)
V3)2480.2 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.28 × 0.14 × 0.08
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.974, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
18262, 4616, 2795
Rint0.038
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.109, 1.00
No. of reflections4616
No. of parameters345
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.15, 0.15

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).

 

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPADST program at IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding

References

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