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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Dec 17;65(Pt 1):o128. doi: 10.1107/S1600536808042074

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

T Maiyalagan a, Venkatesha R Hathwar b, P Manivel a, N Burcu Arslan c, F Nawaz Khan a,*
PMCID: PMC2968048  PMID: 21581589

Abstract

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 ▶); Hill (1986 ▶); Canendo et al. (1997 ▶); Whyte et al. (1996 ▶). For related structures, see: Abid et al. (2006 ▶, 2008 ▶); Hathwar et al. (2007 ▶).graphic file with name e-65-0o128-scheme1.jpg

Experimental

Crystal data

  • C16H12O3

  • M r = 252.26

  • Monoclinic, Inline graphic

  • 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 ▶) T min = 0.974, T max = 0.984

  • 18262 measured reflections

  • 4616 independent reflections

  • 2795 reflections with I > 2σ(I)

  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045

  • wR(F 2) = 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 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042074/nc2128sup1.cif

e-65-0o128-sup1.cif (24.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042074/nc2128Isup2.hkl

e-65-0o128-Isup2.hkl (221.6KB, hkl)

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

Acknowledgments

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

supplementary crystallographic information

Comment

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

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

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: Crystal structure of the title complex, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C16H12O3 F(000) = 1056
Mr = 252.26 Dx = 1.351 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 8668 reflections
a = 15.5949 (15) Å θ = 1.5–25.5°
b = 11.8464 (11) Å µ = 0.09 mm−1
c = 15.1824 (14) Å T = 290 K
β = 117.838 (2)° Block, colourless
V = 2480.2 (4) Å3 0.28 × 0.14 × 0.08 mm
Z = 8
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Data collection

Bruker SMART CCD area-detector diffractometer 4616 independent reflections
Radiation source: fine-focus sealed tube 2795 reflections with I > 2σ(I)
graphite Rint = 0.038
φ and ω scans θmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −18→18
Tmin = 0.974, Tmax = 0.984 k = −13→14
18262 measured reflections l = −18→18
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Refinement

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)] = 0.045 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109 All 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 parameters Δρmax = 0.14 e Å−3
0 restraints Δρmin = −0.15 e Å−3
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.46573 (12) 0.71997 (11) 1.12417 (10) 0.0894 (5)
O2 0.41915 (8) 0.88630 (10) 1.05390 (8) 0.0602 (3)
O3 0.35416 (9) 1.40912 (10) 1.06979 (10) 0.0762 (4)
O4 0.03964 (12) 0.71696 (11) 0.15948 (11) 0.0912 (5)
O5 0.08196 (8) 0.88474 (10) 0.13156 (8) 0.0595 (3)
O6 0.13583 (9) 1.40934 (10) 0.20493 (9) 0.0667 (4)
C1 0.43111 (14) 0.77173 (16) 1.04693 (14) 0.0606 (5)
C2 0.38013 (11) 0.95680 (14) 0.97170 (12) 0.0470 (4)
C3 0.35328 (11) 0.91498 (14) 0.88124 (12) 0.0496 (4)
H3 0.3276 0.9634 0.8267 0.060*
C4 0.33679 (13) 0.75059 (16) 0.77199 (13) 0.0600 (5)
H4 0.3121 0.7967 0.7159 0.072*
C5 0.34738 (13) 0.63695 (17) 0.76232 (14) 0.0667 (5)
H5 0.3305 0.6069 0.6998 0.080*
C6 0.38271 (13) 0.56691 (17) 0.84417 (15) 0.0690 (5)
H6 0.3885 0.4899 0.8364 0.083*
C7 0.40934 (13) 0.61035 (16) 0.93675 (14) 0.0646 (5)
H7 0.4332 0.5630 0.9920 0.077*
C8 0.40056 (12) 0.72591 (15) 0.94798 (12) 0.0503 (4)
C9 0.36294 (11) 0.79755 (14) 0.86563 (12) 0.0475 (4)
C10 0.37489 (11) 1.07382 (14) 1.00008 (12) 0.0467 (4)
C11 0.40524 (12) 1.10565 (15) 1.09812 (12) 0.0551 (5)
H11 0.4297 1.0508 1.1476 0.066*
C12 0.40041 (13) 1.21545 (16) 1.12477 (13) 0.0581 (5)
H12 0.4221 1.2340 1.1913 0.070*
C13 0.36364 (13) 1.29749 (15) 1.05313 (14) 0.0552 (5)
C14 0.33210 (13) 1.26874 (16) 0.95395 (14) 0.0629 (5)
H14 0.3067 1.3238 0.9047 0.076*
C15 0.33854 (13) 1.15925 (15) 0.92883 (13) 0.0593 (5)
H15 0.3181 1.1414 0.8623 0.071*
C16 0.38761 (16) 1.44487 (18) 1.16989 (16) 0.0882 (7)
H16A 0.3474 1.4126 1.1956 0.132*
H16B 0.3846 1.5257 1.1720 0.132*
H16C 0.4534 1.4205 1.2096 0.132*
C17 0.07336 (13) 0.77001 (16) 0.11542 (13) 0.0607 (5)
C18 0.11848 (11) 0.95659 (14) 0.08575 (11) 0.0473 (4)
C19 0.14586 (11) 0.91583 (14) 0.02099 (12) 0.0507 (4)
H19 0.1691 0.9653 −0.0105 0.061*
C20 0.16909 (13) 0.75191 (15) −0.06827 (14) 0.0608 (5)
H20 0.1914 0.7993 −0.1020 0.073*
C21 0.16469 (14) 0.63793 (17) −0.08482 (14) 0.0690 (5)
H21 0.1846 0.6087 −0.1292 0.083*
C22 0.13085 (14) 0.56579 (17) −0.03610 (14) 0.0713 (6)
H22 0.1281 0.4884 −0.0476 0.086*
C23 0.10135 (13) 0.60905 (16) 0.02928 (14) 0.0664 (5)
H23 0.0785 0.5609 0.0620 0.080*
C24 0.10552 (12) 0.72472 (15) 0.04675 (12) 0.0510 (4)
C25 0.14046 (11) 0.79797 (14) −0.00148 (12) 0.0477 (4)
C26 0.12307 (11) 1.07354 (14) 0.11878 (11) 0.0471 (4)
C27 0.09425 (12) 1.10360 (15) 0.18924 (12) 0.0575 (5)
H27 0.0723 1.0476 0.2167 0.069*
C28 0.09700 (13) 1.21374 (15) 0.22010 (13) 0.0584 (5)
H28 0.0772 1.2312 0.2675 0.070*
C29 0.12929 (12) 1.29732 (15) 0.18019 (13) 0.0517 (5)
C30 0.15888 (13) 1.26986 (15) 0.10993 (14) 0.0621 (5)
H30 0.1811 1.3261 0.0829 0.074*
C31 0.15544 (13) 1.16016 (15) 0.08009 (13) 0.0595 (5)
H31 0.1753 1.1432 0.0326 0.071*
C32 0.09712 (14) 1.44297 (16) 0.26951 (14) 0.0770 (6)
H32A 0.0317 1.4163 0.2434 0.115*
H32B 0.0979 1.5238 0.2741 0.115*
H32C 0.1358 1.4114 0.3345 0.115*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.1390 (14) 0.0681 (9) 0.0507 (8) 0.0230 (9) 0.0355 (9) 0.0148 (7)
O2 0.0798 (9) 0.0542 (8) 0.0436 (7) 0.0102 (6) 0.0262 (6) 0.0041 (6)
O3 0.0977 (11) 0.0546 (9) 0.0764 (10) 0.0029 (7) 0.0407 (8) −0.0108 (7)
O4 0.1466 (14) 0.0660 (9) 0.1082 (11) −0.0176 (9) 0.0991 (11) −0.0002 (8)
O5 0.0785 (9) 0.0537 (8) 0.0633 (8) −0.0091 (6) 0.0473 (7) −0.0027 (6)
O6 0.0808 (9) 0.0559 (9) 0.0723 (9) −0.0028 (7) 0.0431 (7) −0.0091 (7)
C1 0.0737 (14) 0.0577 (13) 0.0510 (12) 0.0102 (10) 0.0295 (11) 0.0063 (10)
C2 0.0468 (10) 0.0532 (12) 0.0422 (10) 0.0010 (8) 0.0216 (8) 0.0069 (9)
C3 0.0550 (11) 0.0513 (12) 0.0421 (10) 0.0013 (8) 0.0222 (9) 0.0070 (8)
C4 0.0612 (13) 0.0649 (14) 0.0481 (11) −0.0035 (10) 0.0207 (10) −0.0031 (9)
C5 0.0642 (13) 0.0718 (15) 0.0568 (13) −0.0066 (11) 0.0220 (11) −0.0176 (11)
C6 0.0734 (14) 0.0573 (13) 0.0729 (14) 0.0018 (10) 0.0313 (12) −0.0088 (11)
C7 0.0747 (14) 0.0571 (14) 0.0642 (13) 0.0108 (10) 0.0343 (11) 0.0048 (10)
C8 0.0505 (11) 0.0533 (12) 0.0491 (11) 0.0024 (9) 0.0249 (9) 0.0002 (9)
C9 0.0424 (10) 0.0560 (12) 0.0446 (11) −0.0041 (8) 0.0208 (9) −0.0018 (9)
C10 0.0425 (10) 0.0514 (11) 0.0458 (10) −0.0009 (8) 0.0203 (8) 0.0010 (9)
C11 0.0613 (12) 0.0582 (13) 0.0469 (11) 0.0034 (9) 0.0261 (9) 0.0023 (9)
C12 0.0663 (13) 0.0611 (13) 0.0477 (11) 0.0006 (10) 0.0271 (10) −0.0052 (10)
C13 0.0554 (12) 0.0506 (13) 0.0622 (13) −0.0029 (9) 0.0296 (10) −0.0074 (10)
C14 0.0723 (14) 0.0546 (13) 0.0527 (12) 0.0058 (10) 0.0215 (10) 0.0072 (10)
C15 0.0704 (13) 0.0562 (13) 0.0458 (11) 0.0014 (10) 0.0226 (10) −0.0015 (9)
C16 0.1071 (18) 0.0744 (16) 0.0891 (16) −0.0108 (13) 0.0508 (14) −0.0317 (13)
C17 0.0746 (14) 0.0555 (13) 0.0621 (12) −0.0061 (10) 0.0404 (11) 0.0017 (10)
C18 0.0462 (10) 0.0534 (12) 0.0451 (10) −0.0041 (8) 0.0236 (9) 0.0041 (8)
C19 0.0535 (11) 0.0532 (12) 0.0514 (10) −0.0030 (8) 0.0296 (9) 0.0036 (9)
C20 0.0659 (13) 0.0609 (14) 0.0676 (12) −0.0032 (10) 0.0413 (11) −0.0041 (10)
C21 0.0744 (14) 0.0692 (14) 0.0755 (14) 0.0024 (11) 0.0451 (12) −0.0095 (11)
C22 0.0824 (15) 0.0551 (13) 0.0783 (14) 0.0029 (10) 0.0391 (12) −0.0053 (11)
C23 0.0775 (14) 0.0581 (14) 0.0695 (13) −0.0065 (10) 0.0393 (11) −0.0005 (10)
C24 0.0512 (11) 0.0520 (12) 0.0501 (10) −0.0006 (9) 0.0237 (9) −0.0003 (9)
C25 0.0428 (10) 0.0552 (12) 0.0444 (10) 0.0001 (8) 0.0198 (9) 0.0005 (9)
C26 0.0442 (10) 0.0524 (11) 0.0453 (10) −0.0005 (8) 0.0213 (8) 0.0017 (8)
C27 0.0646 (12) 0.0618 (13) 0.0562 (11) −0.0057 (9) 0.0365 (10) 0.0009 (9)
C28 0.0684 (13) 0.0622 (13) 0.0551 (11) −0.0019 (10) 0.0377 (10) −0.0064 (10)
C29 0.0519 (11) 0.0509 (12) 0.0523 (11) 0.0009 (9) 0.0243 (9) −0.0022 (9)
C30 0.0728 (14) 0.0543 (12) 0.0749 (13) −0.0098 (10) 0.0478 (12) −0.0024 (10)
C31 0.0731 (13) 0.0595 (13) 0.0634 (12) −0.0060 (10) 0.0465 (11) −0.0055 (10)
C32 0.0862 (15) 0.0708 (15) 0.0819 (14) 0.0036 (11) 0.0459 (13) −0.0175 (11)
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Geometric parameters (Å, °)

O1—C1 1.2048 (19) C14—H14 0.9300
O2—C1 1.381 (2) C15—H15 0.9300
O2—C2 1.3842 (18) C16—H16A 0.9600
O3—C13 1.3672 (19) C16—H16B 0.9600
O3—C16 1.422 (2) C16—H16C 0.9600
O4—C17 1.2032 (19) C17—C24 1.454 (2)
O5—C17 1.3765 (19) C18—C19 1.332 (2)
O5—C18 1.3794 (17) C18—C26 1.464 (2)
O6—C29 1.3700 (18) C19—C25 1.431 (2)
O6—C32 1.4272 (19) C19—H19 0.9300
C1—C8 1.453 (2) C20—C21 1.369 (2)
C2—C3 1.330 (2) C20—C25 1.396 (2)
C2—C10 1.465 (2) C20—H20 0.9300
C3—C9 1.431 (2) C21—C22 1.386 (3)
C3—H3 0.9300 C21—H21 0.9300
C4—C5 1.373 (2) C22—C23 1.373 (2)
C4—C9 1.398 (2) C22—H22 0.9300
C4—H4 0.9300 C23—C24 1.391 (2)
C5—C6 1.377 (2) C23—H23 0.9300
C5—H5 0.9300 C24—C25 1.400 (2)
C6—C7 1.367 (2) C26—C27 1.387 (2)
C6—H6 0.9300 C26—C31 1.389 (2)
C7—C8 1.394 (2) C27—C28 1.380 (2)
C7—H7 0.9300 C27—H27 0.9300
C8—C9 1.394 (2) C28—C29 1.373 (2)
C10—C11 1.387 (2) C28—H28 0.9300
C10—C15 1.394 (2) C29—C30 1.384 (2)
C11—C12 1.375 (2) C30—C31 1.369 (2)
C11—H11 0.9300 C30—H30 0.9300
C12—C13 1.369 (2) C31—H31 0.9300
C12—H12 0.9300 C32—H32A 0.9600
C13—C14 1.391 (2) C32—H32B 0.9600
C14—C15 1.369 (2) C32—H32C 0.9600
C1—O2—C2 122.83 (14) H16A—C16—H16C 109.5
C13—O3—C16 117.94 (15) H16B—C16—H16C 109.5
C17—O5—C18 123.25 (13) O4—C17—O5 116.63 (16)
C29—O6—C32 117.23 (14) O4—C17—C24 126.34 (18)
O1—C1—O2 116.16 (16) O5—C17—C24 117.03 (15)
O1—C1—C8 126.72 (19) C19—C18—O5 119.92 (15)
O2—C1—C8 117.12 (16) C19—C18—C26 127.93 (15)
C3—C2—O2 120.00 (16) O5—C18—C26 112.14 (13)
C3—C2—C10 128.46 (16) C18—C19—C25 121.77 (15)
O2—C2—C10 111.54 (14) C18—C19—H19 119.1
C2—C3—C9 121.76 (16) C25—C19—H19 119.1
C2—C3—H3 119.1 C21—C20—C25 120.88 (17)
C9—C3—H3 119.1 C21—C20—H20 119.6
C5—C4—C9 120.42 (17) C25—C20—H20 119.6
C5—C4—H4 119.8 C20—C21—C22 120.60 (18)
C9—C4—H4 119.8 C20—C21—H21 119.7
C4—C5—C6 120.79 (18) C22—C21—H21 119.7
C4—C5—H5 119.6 C23—C22—C21 119.68 (19)
C6—C5—H5 119.6 C23—C22—H22 120.2
C7—C6—C5 120.17 (19) C21—C22—H22 120.2
C7—C6—H6 119.9 C22—C23—C24 120.24 (18)
C5—C6—H6 119.9 C22—C23—H23 119.9
C6—C7—C8 119.70 (18) C24—C23—H23 119.9
C6—C7—H7 120.2 C23—C24—C25 120.39 (16)
C8—C7—H7 120.2 C23—C24—C17 119.93 (16)
C9—C8—C7 120.83 (16) C25—C24—C17 119.69 (17)
C9—C8—C1 119.83 (17) C20—C25—C24 118.20 (16)
C7—C8—C1 119.34 (17) C20—C25—C19 123.49 (15)
C8—C9—C4 118.06 (16) C24—C25—C19 118.31 (15)
C8—C9—C3 118.44 (15) C27—C26—C31 116.70 (16)
C4—C9—C3 123.50 (16) C27—C26—C18 121.72 (15)
C11—C10—C15 116.53 (16) C31—C26—C18 121.58 (14)
C11—C10—C2 122.33 (16) C28—C27—C26 122.33 (16)
C15—C10—C2 121.13 (15) C28—C27—H27 118.8
C12—C11—C10 122.34 (17) C26—C27—H27 118.8
C12—C11—H11 118.8 C29—C28—C27 119.43 (16)
C10—C11—H11 118.8 C29—C28—H28 120.3
C13—C12—C11 119.88 (17) C27—C28—H28 120.3
C13—C12—H12 120.1 O6—C29—C28 124.97 (16)
C11—C12—H12 120.1 O6—C29—C30 115.46 (16)
O3—C13—C12 125.53 (17) C28—C29—C30 119.57 (17)
O3—C13—C14 115.03 (17) C31—C30—C29 120.16 (17)
C12—C13—C14 119.44 (17) C31—C30—H30 119.9
C15—C14—C13 119.93 (17) C29—C30—H30 119.9
C15—C14—H14 120.0 C30—C31—C26 121.81 (16)
C13—C14—H14 120.0 C30—C31—H31 119.1
C14—C15—C10 121.87 (16) C26—C31—H31 119.1
C14—C15—H15 119.1 O6—C32—H32A 109.5
C10—C15—H15 119.1 O6—C32—H32B 109.5
O3—C16—H16A 109.5 H32A—C32—H32B 109.5
O3—C16—H16B 109.5 O6—C32—H32C 109.5
H16A—C16—H16B 109.5 H32A—C32—H32C 109.5
O3—C16—H16C 109.5 H32B—C32—H32C 109.5
C2—O2—C1—O1 −179.82 (16) C18—O5—C17—O4 −179.43 (17)
C2—O2—C1—C8 −0.1 (2) C18—O5—C17—C24 0.4 (2)
C1—O2—C2—C3 −0.7 (2) C17—O5—C18—C19 1.2 (2)
C1—O2—C2—C10 179.49 (14) C17—O5—C18—C26 −177.86 (14)
O2—C2—C3—C9 0.4 (2) O5—C18—C19—C25 −1.3 (2)
C10—C2—C3—C9 −179.86 (14) C26—C18—C19—C25 177.58 (15)
C9—C4—C5—C6 0.8 (3) C25—C20—C21—C22 0.6 (3)
C4—C5—C6—C7 −1.1 (3) C20—C21—C22—C23 0.1 (3)
C5—C6—C7—C8 0.0 (3) C21—C22—C23—C24 −0.1 (3)
C6—C7—C8—C9 1.4 (3) C22—C23—C24—C25 −0.5 (3)
C6—C7—C8—C1 −178.60 (17) C22—C23—C24—C17 179.46 (17)
O1—C1—C8—C9 −179.05 (18) O4—C17—C24—C23 −2.0 (3)
O2—C1—C8—C9 1.3 (2) O5—C17—C24—C23 178.20 (15)
O1—C1—C8—C7 1.0 (3) O4—C17—C24—C25 177.94 (19)
O2—C1—C8—C7 −178.74 (15) O5—C17—C24—C25 −1.9 (2)
C7—C8—C9—C4 −1.7 (2) C21—C20—C25—C24 −1.1 (3)
C1—C8—C9—C4 178.31 (15) C21—C20—C25—C19 178.23 (16)
C7—C8—C9—C3 178.43 (14) C23—C24—C25—C20 1.1 (2)
C1—C8—C9—C3 −1.6 (2) C17—C24—C25—C20 −178.86 (15)
C5—C4—C9—C8 0.6 (2) C23—C24—C25—C19 −178.30 (15)
C5—C4—C9—C3 −179.54 (16) C17—C24—C25—C19 1.8 (2)
C2—C3—C9—C8 0.7 (2) C18—C19—C25—C20 −179.51 (16)
C2—C3—C9—C4 −179.12 (16) C18—C19—C25—C24 −0.2 (2)
C3—C2—C10—C11 179.61 (16) C19—C18—C26—C27 −178.18 (17)
O2—C2—C10—C11 −0.6 (2) O5—C18—C26—C27 0.8 (2)
C3—C2—C10—C15 −0.3 (3) C19—C18—C26—C31 2.6 (3)
O2—C2—C10—C15 179.50 (14) O5—C18—C26—C31 −178.40 (15)
C15—C10—C11—C12 −0.2 (2) C31—C26—C27—C28 0.1 (3)
C2—C10—C11—C12 179.95 (15) C18—C26—C27—C28 −179.13 (15)
C10—C11—C12—C13 0.7 (3) C26—C27—C28—C29 0.0 (3)
C16—O3—C13—C12 2.0 (3) C32—O6—C29—C28 −6.6 (2)
C16—O3—C13—C14 −178.23 (17) C32—O6—C29—C30 173.92 (16)
C11—C12—C13—O3 179.38 (15) C27—C28—C29—O6 −179.69 (15)
C11—C12—C13—C14 −0.4 (3) C27—C28—C29—C30 −0.2 (3)
O3—C13—C14—C15 179.79 (16) O6—C29—C30—C31 179.88 (15)
C12—C13—C14—C15 −0.4 (3) C28—C29—C30—C31 0.4 (3)
C13—C14—C15—C10 0.9 (3) C29—C30—C31—C26 −0.3 (3)
C11—C10—C15—C14 −0.7 (3) C27—C26—C31—C30 0.0 (3)
C2—C10—C15—C14 179.22 (15) C18—C26—C31—C30 179.28 (16)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2128).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042074/nc2128sup1.cif

e-65-0o128-sup1.cif (24.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042074/nc2128Isup2.hkl

e-65-0o128-Isup2.hkl (221.6KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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