organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

9-[(E)-2-(2-Meth­­oxy­phen­yl)ethen­yl]-3,4,5,6,7,9-hexa­hydro-2H-xanthene-1,8-dione

aAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and bCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
*Correspondence e-mail: j9601@kist.re.kr

(Received 4 January 2012; accepted 12 January 2012; online 18 January 2012)

In the title compound, C22H22O4, the two cyclo­hexenone rings adopt half-chair conformations, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating from the plane of the other four atoms by 0.142 (2) and 0.287 (2)Å, respectively. In the crystal, weak C—H⋯O hydrogen bonds link mol­ecules into chains running parallel to the a axis.

Related literature

For the biological activity of xanthenes and their derivatives, see: Lee et al. (2011[Lee, J. K., Min, S.-J., Cho, Y. S., Cha, J. H. & Sato, H. (2011). Acta Cryst. E67, o3407.]). For related structures of xanthenes, see: Asad et al. (2012[Asad, M., Oo, C.-W., Osman, H., Fun, H.-K. & Arshad, S. (2012). Acta Cryst. E68, o38.]); Fun et al. (2011[Fun, H.-K., Loh, W.-S., Rajesh, K., Vijayakumar, V. & Sarveswari, S. (2011). Acta Cryst. E67, o1876-o1877.]); Mehdi et al. (2011[Mehdi, S. H., Sulaiman, O., Ghalib, R. M., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1719-o1720.]).

[Scheme 1]

Experimental

Crystal data
  • C22H22O4

  • Mr = 350.41

  • Monoclinic, P 21 /c

  • a = 8.5396 (5) Å

  • b = 9.9243 (7) Å

  • c = 21.9501 (13) Å

  • β = 102.5455 (14)°

  • V = 1815.85 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.821, Tmax = 0.983

  • 17353 measured reflections

  • 4100 independent reflections

  • 3248 reflections with F2 > 2σ(F2)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.136

  • S = 1.08

  • 4100 reflections

  • 244 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14B⋯O2i 0.97 2.43 3.3231 (18) 153
Symmetry code: (i) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

As part of our ongoing study of the substituent effect on the solid state structures of xanthene derivatives (Lee et al., 2011).

In C22H22O4, (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Asad et al., 2012; Fun et al., 2011; Mehdi et al., 2011). The methoxyphenyl group in molecule is almost planar [C26–O4–C25–C26 = -174.54 (16)°]. The two cyclohexenone rings in display half-chair conformation, Fig. 1. Atom C4 lies 0.621 (2)Å above the plane of the remaining 5 atoms of the ring containing atoms C1 to C6. Atom C9 lies 0.621 (2)Å above the plane of the remaining 5 atoms of the ring containing atoms C7 to C12. In the six-membered xanthene ring adopts a flattened boat conformation with the O1 and methine, 13, atoms deviating from the plane of the other four atoms by 0.142 (2)Å and 0.287 (2) Å.

In the crystal, a weak intermolecular C—H···O hydrogen bonds (Table 1) links the molecules into chains which run parallel to the a-axis.

Related literature top

For the biological activity of xanthenes and their derivatives, see: Lee et al. (2011). For related structures of xanthenes, see: Asad et al. (2012); Fun et al. (2011); Mehdi et al. (2011).

Experimental top

To a solution of 3-Hydroxy-2-[(2(E))-1-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-3- (2-methoxyphenyl)prop-2-en-1-yl]cyclohex-2-en-1-one (1.25 mmol) was added methanol(12.5 mL) and catalytic amounts of sulfuric acid(0.2 mL) under a nitrogen atmosphere. After stirring for 3 h, the solvent was evaporated and the remaining residue dissolved in ethyl acetate. The mixture was neutralized with saturated sodium bicarbonate and the solution was extracted with ethyl acetate. The resulting solid residue was purified by recrystallization from ethanol and methylene chloride to afford white needle crystals suitable for X-ray analysis.

Refinement top

Atoms H18 and H19 were located from a difference Fourier map and refined freely [C18—H = 0.965 (18) Å and C19—H = 1.00 (2) Å]. The remaining hydrogen atoms were positioned geometrically and refined using a riding model with [C—H = 0.93–0.97 Å] and Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoid.
9-[(E)-2-(2-Methoxyphenyl)ethenyl]-3,4,5,6,7,9-hexahydro-2H- xanthene-1,8-dione top
Crystal data top
C22H22O4F(000) = 744.00
Mr = 350.41Dx = 1.282 Mg m3
Monoclinic, P21/cMelting point: 427 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71075 Å
a = 8.5396 (5) ÅCell parameters from 13636 reflections
b = 9.9243 (7) Åθ = 3.2–27.4°
c = 21.9501 (13) ŵ = 0.09 mm1
β = 102.5455 (14)°T = 296 K
V = 1815.85 (19) Å3Block, colourless
Z = 40.40 × 0.20 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3248 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.018
ω scansθmax = 27.4°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 1011
Tmin = 0.821, Tmax = 0.983k = 1212
17353 measured reflectionsl = 2826
4100 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0784P)2 + 0.1912P]
where P = (Fo2 + 2Fc2)/3
4100 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.21 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C22H22O4V = 1815.85 (19) Å3
Mr = 350.41Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.5396 (5) ŵ = 0.09 mm1
b = 9.9243 (7) ÅT = 296 K
c = 21.9501 (13) Å0.40 × 0.20 × 0.20 mm
β = 102.5455 (14)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4100 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
3248 reflections with F2 > 2σ(F2)
Tmin = 0.821, Tmax = 0.983Rint = 0.018
17353 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.25 e Å3
4100 reflectionsΔρmin = 0.21 e Å3
244 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.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.24674 (12)0.65221 (10)0.34715 (4)0.0507 (3)
O20.20315 (12)0.36602 (11)0.29337 (6)0.0626 (3)
O30.23752 (13)0.39194 (11)0.16669 (5)0.0577 (3)
O40.19930 (17)0.46300 (12)0.02525 (5)0.0704 (4)
C50.01484 (14)0.51591 (12)0.31309 (6)0.0390 (3)
C60.11815 (15)0.44136 (14)0.33047 (6)0.0454 (3)
C70.13815 (18)0.45708 (18)0.39689 (7)0.0592 (4)
C80.09477 (19)0.59700 (18)0.42221 (7)0.0599 (4)
C90.07687 (19)0.63093 (17)0.41853 (6)0.0556 (4)
C100.10633 (15)0.59497 (13)0.35617 (6)0.0423 (3)
C110.30878 (15)0.60472 (13)0.29859 (5)0.0404 (3)
C120.47915 (17)0.64695 (16)0.30453 (7)0.0530 (4)
C130.52343 (17)0.64744 (16)0.24128 (8)0.0552 (4)
C140.47594 (18)0.51597 (17)0.20733 (8)0.0563 (4)
C150.30516 (16)0.47312 (13)0.20547 (6)0.0443 (3)
C160.22483 (14)0.52783 (12)0.25284 (5)0.0381 (3)
C170.04913 (14)0.49631 (12)0.24894 (5)0.0378 (3)
C180.05446 (14)0.58600 (13)0.20051 (6)0.0395 (3)
C190.14029 (15)0.54299 (14)0.14667 (6)0.0428 (3)
C200.23750 (15)0.62750 (13)0.09714 (6)0.0423 (3)
C210.30228 (17)0.75056 (15)0.10949 (7)0.0511 (4)
C220.3946 (2)0.82777 (17)0.06197 (8)0.0637 (5)
C230.4239 (3)0.78154 (19)0.00164 (8)0.0697 (5)
C240.3609 (2)0.65984 (18)0.01266 (7)0.0656 (5)
C250.26841 (18)0.58327 (15)0.03475 (6)0.0504 (4)
C260.2132 (4)0.4176 (3)0.03727 (8)0.0919 (8)
H7A0.24870.43810.39840.0711*
H7B0.07060.39180.42320.0711*
H8A0.10540.60180.46530.0719*
H8B0.16770.66220.39820.0719*
H9A0.09580.72650.42600.0667*
H9B0.15100.58190.45070.0667*
H12A0.54910.58550.33220.0636*
H12B0.49430.73650.32260.0636*
H13A0.46940.72160.21650.0662*
H13B0.63820.66080.24670.0662*
H14A0.49020.52460.16490.0676*
H14B0.54770.44560.22750.0676*
H170.02890.40200.23650.0453*
H210.28350.78190.15040.0613*
H220.43620.91010.07110.0765*
H230.48690.83250.03000.0836*
H240.38040.62970.05370.0787*
H26A0.17310.48570.06090.1102*
H26B0.32390.40000.05580.1102*
H26C0.15200.33640.03720.1102*
H180.0539 (19)0.6800 (18)0.2117 (8)0.056 (5)*
H190.138 (2)0.444 (2)0.1371 (8)0.063 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0564 (6)0.0566 (6)0.0404 (5)0.0216 (5)0.0137 (4)0.0100 (4)
O20.0491 (6)0.0578 (7)0.0788 (8)0.0151 (5)0.0095 (6)0.0031 (6)
O30.0601 (6)0.0613 (7)0.0500 (6)0.0067 (5)0.0082 (5)0.0137 (5)
O40.1119 (10)0.0573 (7)0.0361 (6)0.0187 (7)0.0031 (6)0.0024 (5)
C50.0399 (6)0.0381 (7)0.0375 (6)0.0010 (5)0.0052 (5)0.0046 (5)
C60.0379 (7)0.0420 (7)0.0549 (8)0.0011 (5)0.0073 (6)0.0097 (6)
C70.0505 (8)0.0719 (11)0.0580 (9)0.0028 (7)0.0179 (7)0.0191 (8)
C80.0641 (9)0.0766 (11)0.0430 (8)0.0088 (8)0.0204 (7)0.0077 (7)
C90.0664 (10)0.0630 (10)0.0388 (7)0.0083 (7)0.0145 (7)0.0032 (6)
C100.0483 (7)0.0430 (7)0.0359 (6)0.0056 (5)0.0095 (5)0.0030 (5)
C110.0443 (7)0.0407 (7)0.0355 (6)0.0055 (5)0.0074 (5)0.0041 (5)
C120.0464 (8)0.0569 (9)0.0533 (8)0.0141 (6)0.0055 (6)0.0024 (7)
C130.0456 (8)0.0576 (9)0.0658 (9)0.0008 (6)0.0198 (7)0.0071 (7)
C140.0485 (8)0.0620 (10)0.0607 (9)0.0086 (7)0.0168 (7)0.0000 (7)
C150.0485 (7)0.0427 (7)0.0402 (7)0.0091 (6)0.0062 (6)0.0033 (6)
C160.0410 (6)0.0363 (7)0.0353 (6)0.0004 (5)0.0045 (5)0.0043 (5)
C170.0412 (7)0.0338 (6)0.0360 (6)0.0027 (5)0.0031 (5)0.0013 (5)
C180.0407 (7)0.0373 (7)0.0388 (6)0.0019 (5)0.0052 (5)0.0012 (5)
C190.0479 (7)0.0412 (7)0.0369 (7)0.0015 (6)0.0042 (6)0.0001 (5)
C200.0438 (7)0.0432 (7)0.0377 (6)0.0031 (5)0.0040 (5)0.0040 (5)
C210.0532 (8)0.0506 (8)0.0489 (8)0.0032 (6)0.0098 (6)0.0034 (6)
C220.0654 (10)0.0534 (9)0.0720 (11)0.0142 (8)0.0144 (8)0.0146 (8)
C230.0723 (11)0.0703 (11)0.0604 (10)0.0116 (9)0.0013 (8)0.0249 (8)
C240.0814 (12)0.0664 (11)0.0415 (8)0.0013 (9)0.0033 (7)0.0109 (7)
C250.0604 (9)0.0479 (8)0.0391 (7)0.0010 (6)0.0029 (6)0.0043 (6)
C260.159 (3)0.0715 (13)0.0406 (9)0.0177 (13)0.0119 (11)0.0068 (8)
Geometric parameters (Å, º) top
O1—C101.3794 (17)C22—C231.372 (3)
O1—C111.3727 (17)C23—C241.386 (3)
O2—C61.2216 (17)C24—C251.388 (2)
O3—C151.2222 (17)C7—H7A0.970
O4—C251.367 (2)C7—H7B0.970
O4—C261.425 (3)C8—H8A0.970
C5—C61.4734 (19)C8—H8B0.970
C5—C101.3414 (17)C9—H9A0.970
C5—C171.5118 (19)C9—H9B0.970
C6—C71.512 (3)C12—H12A0.970
C7—C81.512 (3)C12—H12B0.970
C8—C91.523 (3)C13—H13A0.970
C9—C101.488 (2)C13—H13B0.970
C11—C121.492 (2)C14—H14A0.970
C11—C161.3386 (16)C14—H14B0.970
C12—C131.516 (3)C17—H170.980
C13—C141.514 (3)C18—H180.965 (18)
C14—C151.511 (2)C19—H191.00 (2)
C15—C161.4685 (19)C21—H210.930
C16—C171.5168 (17)C22—H220.930
C17—C181.5154 (16)C23—H230.930
C18—C191.3190 (17)C24—H240.930
C19—C201.4773 (18)C26—H26A0.960
C20—C211.391 (2)C26—H26B0.960
C20—C251.4074 (19)C26—H26C0.960
C21—C221.393 (3)
O1···C172.8824 (14)C16···H21i3.2029
O2···C103.5306 (16)C17···H21i3.3906
O2···C172.8596 (18)C17···H18i3.254 (18)
O2···C183.4143 (19)C18···H13Bii3.1026
O3···C113.5280 (16)C18···H17v3.4151
O3···C172.8605 (18)C19···H9Ai3.5797
O3···C183.3588 (18)C19···H13Bii3.4021
O3···C193.4977 (17)C19···H14Aii3.2706
O4···C192.7210 (17)C20···H14Aii3.1875
C5···C82.870 (3)C21···H13Aii3.3745
C5···C112.7434 (19)C21···H13Bii3.2853
C6···C92.941 (2)C21···H14Aii3.2528
C6···C183.342 (2)C21···H26Bxi3.4900
C7···C102.800 (3)C22···H7Axii3.5191
C10···C162.7585 (19)C22···H9Bv3.3189
C10···C183.3955 (18)C22···H23xiii3.5464
C11···C142.840 (3)C22···H26Bxi3.2808
C11···C183.3749 (16)C23···H8Axiv3.2128
C12···C152.9169 (19)C23···H8Bxiv3.5230
C13···C162.873 (2)C23···H22xiii3.5367
C15···C183.2485 (19)C23···H26Bxi3.2259
C16···C193.4668 (16)C24···H8Axiv3.3244
C18···C213.0497 (18)C24···H8Bxiv3.3273
C20···C232.796 (2)C24···H26Bxi3.4078
C21···C242.769 (3)C26···H7Bxv3.4816
C22···C252.772 (3)C26···H9Ai3.0831
C24···C262.821 (3)C26···H14Aiv3.2999
O2···C11i3.2897 (17)H7A···C12ii3.4446
O2···C12i3.5636 (18)H7A···C22xvi3.5191
O2···C13i3.4440 (18)H7A···H9Bix3.2417
O2···C14ii3.3231 (18)H7A···H12Aii2.4784
O2···C16i3.4995 (17)H7A···H13Ai3.5313
O2···C18i3.5287 (17)H7A···H22xvi2.9242
O3···C8i3.582 (2)H7A···H26Cx3.0971
O3···C12iii3.3913 (19)H7B···C8ix3.3822
O3···C13iii3.5135 (19)H7B···C9ix3.4933
O3···C26iv3.381 (3)H7B···C26x3.4816
O4···C9i3.594 (2)H7B···H8Aix2.5805
C8···O3v3.582 (2)H7B···H9Aix3.5632
C9···O4v3.594 (2)H7B···H9Bix3.0054
C11···O2v3.2897 (17)H7B···H26Cx2.5748
C12···O2v3.5636 (18)H8A···C7ix3.3300
C12···O3vi3.3913 (19)H8A···C8ix3.3287
C13···O2v3.4440 (18)H8A···C9ix3.4102
C13···O3vi3.5135 (19)H8A···C23xvii3.2128
C14···O2vii3.3231 (18)H8A···C24xvii3.3244
C16···O2v3.4995 (17)H8A···H7Bix2.5805
C18···O2v3.5287 (17)H8A···H8Aix2.9077
C26···O3iv3.381 (3)H8A···H9Bix2.6817
O1···H9A2.4835H8A···H23xvii3.3459
O1···H9B2.6691H8A···H24xvii3.5166
O1···H12A2.7531H8A···H26Cv3.3528
O1···H12B2.4400H8B···O3v2.6864
O1···H183.491 (14)H8B···C12ii3.2638
O2···H7A2.5240H8B···C23xvii3.5230
O2···H7B2.8402H8B···C24xvii3.3273
O2···H172.5864H8B···H12Aii2.6466
O3···H14A2.5356H8B···H12Bii3.0898
O3···H14B2.7472H8B···H13Bii3.3780
O3···H172.5913H8B···H23xvii3.4318
O3···H193.176 (17)H8B···H24xvii3.0840
O4···H242.6398H9A···O3v3.5237
O4···H192.403 (17)H9A···O4v2.6506
C5···H7A3.3165H9A···C19v3.5797
C5···H7B2.9423H9A···C26v3.0831
C5···H8B3.0486H9A···H7Bix3.5632
C5···H9A3.2000H9A···H23viii3.5333
C5···H9B3.0614H9A···H26Bv3.5306
C5···H182.716 (17)H9A···H26Cv2.6222
C6···H8A3.3407H9A···H19v2.6340
C6···H8B2.7324H9B···C7ix3.3941
C6···H9B3.3988H9B···C8ix3.4281
C6···H172.6669H9B···C22i3.3189
C7···H9A3.3156H9B···H7Aix3.2417
C7···H9B2.7851H9B···H7Bix3.0054
C9···H7A3.3243H9B···H8Aix2.6817
C9···H7B2.6989H9B···H22i3.0932
C10···H7B3.0788H9B···H23viii3.1459
C10···H8A3.2998H9B···H26Cv3.1600
C10···H8B2.7770H12A···O2vii3.2759
C10···H173.2020H12A···O3vi3.5430
C10···H183.279 (15)H12A···C6vii3.1890
C11···H13A2.7476H12A···C7vii3.0207
C11···H13B3.3028H12A···C8vii3.2487
C11···H14B3.2370H12A···H7Avii2.4784
C11···H173.1942H12A···H8Bvii2.6466
C11···H183.350 (15)H12A···H22i3.0580
C12···H14A3.3179H12A···H23viii3.2099
C12···H14B2.7616H12B···O2v3.4010
C14···H12A2.7637H12B···O3vi2.7289
C14···H12B3.3231H12B···C14vi2.8748
C15···H12A3.2873H12B···C15vi3.0475
C15···H13A2.8211H12B···H8Bvii3.0898
C15···H13B3.3550H12B···H14Avi2.8735
C15···H172.6877H12B···H14Bvi2.3401
C16···H12A2.9892H12B···H23viii3.2759
C16···H12B3.2244H12B···H24viii3.0026
C16···H13A3.0694H13A···O2v2.6570
C16···H14A3.2814H13A···O3vi3.5930
C16···H14B3.0409H13A···C14vi3.3485
C16···H182.798 (16)H13A···C15vi3.3823
C17···H192.674 (16)H13A···C21vii3.3745
C18···H212.8076H13A···H7Av3.5313
C19···H172.5875H13A···H14Bvi2.5611
C19···H212.6773H13A···H21vii2.8718
C20···H223.2638H13B···O2vii3.2921
C20···H243.2712H13B···O3vi3.0209
C20···H182.710 (15)H13B···C5vii3.5354
C21···H233.2289H13B···C6vii3.2845
C21···H182.821 (15)H13B···C15vi3.2748
C21···H193.346 (19)H13B···C18vii3.1026
C22···H243.2347H13B···C19vii3.4021
C23···H213.2240H13B···C21vii3.2853
C24···H223.2365H13B···H8Bvii3.3780
C24···H26A2.7240H13B···H14Bvi3.3504
C24···H26B2.7887H13B···H21vii2.6425
C25···H213.2381H13B···H18vii2.9010
C25···H233.2351H14A···C19vii3.2706
C25···H26A2.5989H14A···C20vii3.1875
C25···H26B2.6594H14A···C21vii3.2528
C25···H26C3.1889H14A···C26iv3.2999
C25···H192.664 (17)H14A···H12Biii2.8735
C26···H242.5253H14A···H21vii3.2594
H7A···H8A2.3466H14A···H24iv2.8601
H7A···H8B2.3287H14A···H26Aiv3.1406
H7B···H8A2.3240H14A···H26Biv2.6140
H7B···H8B2.8264H14A···H19vii3.4518
H7B···H9B2.6469H14B···O2vii2.4300
H8A···H9A2.4231H14B···C6vii3.2328
H8A···H9B2.2893H14B···C12iii3.0435
H8B···H9A2.2903H14B···C13iii3.1272
H8B···H9B2.8295H14B···H12Biii2.3401
H12A···H13A2.8269H14B···H13Aiii2.5611
H12A···H13B2.2977H14B···H13Biii3.3504
H12A···H14B2.6837H17···C18i3.4151
H12B···H13A2.2976H17···H21i3.1574
H12B···H13B2.3951H17···H18i2.4669
H13A···H14A2.2853H21···C5v3.2403
H13A···H14B2.8167H21···C10v3.4721
H13B···H14A2.3803H21···C11v3.4161
H13B···H14B2.2784H21···C13ii3.1484
H17···H182.8706H21···C16v3.2029
H17···H192.3715H21···C17v3.3906
H21···H222.3157H21···H13Aii2.8718
H21···H182.3526H21···H13Bii2.6425
H22···H232.2996H21···H14Aii3.2594
H23···H242.3138H21···H17v3.1574
H24···H26A2.3072H22···O1v3.2171
H24···H26B2.3327H22···C10v3.4490
H24···H26C3.4785H22···C11v3.4272
H18···H192.86 (3)H22···C23xiii3.5367
O1···H22i3.2171H22···H7Axii2.9242
O1···H23viii3.1309H22···H9Bv3.0932
O1···H19v3.086 (19)H22···H12Av3.0580
O2···H12Aii3.2759H22···H22xiii3.5533
O2···H12Bi3.4010H22···H23xiii2.7407
O2···H13Ai2.6570H23···O1xviii3.1309
O2···H13Bii3.2921H23···C12xviii3.5857
O2···H14Bii2.4300H23···C22xiii3.5464
O2···H18i2.889 (17)H23···H8Axiv3.3459
O3···H8Bi2.6864H23···H8Bxiv3.4318
O3···H9Ai3.5237H23···H9Axviii3.5333
O3···H12Aiii3.5430H23···H9Bxviii3.1459
O3···H12Biii2.7289H23···H12Axviii3.2099
O3···H13Aiii3.5930H23···H12Bxviii3.2759
O3···H13Biii3.0209H23···H22xiii2.7407
O3···H24iv2.9995H23···H26Bxi3.5780
O3···H26Aiv2.5713H24···O3iv2.9995
O3···H26Biv3.3935H24···C14iv3.5955
O4···H9Ai2.6506H24···H8Axiv3.5166
O4···H26Aiv3.1469H24···H8Bxiv3.0840
O4···H26Civ3.5623H24···H12Bxviii3.0026
C5···H13Bii3.5354H24···H14Aiv2.8601
C5···H21i3.2403H26A···O3iv2.5713
C5···H18i3.406 (18)H26A···O4iv3.1469
C6···H12Aii3.1890H26A···C15iv3.1544
C6···H13Bii3.2845H26A···H14Aiv3.1406
C6···H14Bii3.2328H26A···H26Aiv3.5410
C6···H18i3.215 (18)H26A···H26Civ3.5872
C7···H8Aix3.3300H26A···H19iv3.5032
C7···H9Bix3.3941H26B···O3iv3.3935
C7···H12Aii3.0207H26B···C14iv3.4019
C7···H26Cx3.2654H26B···C15iv3.5549
C8···H7Bix3.3822H26B···C21xi3.4900
C8···H8Aix3.3287H26B···C22xi3.2808
C8···H9Bix3.4281H26B···C23xi3.2259
C8···H12Aii3.2487H26B···C24xi3.4078
C9···H7Bix3.4933H26B···H9Ai3.5306
C9···H8Aix3.4102H26B···H14Aiv2.6140
C9···H26Cv3.2607H26B···H23xi3.5780
C9···H19v3.423 (19)H26C···O4iv3.5623
C10···H21i3.4721H26C···C7xv3.2654
C10···H22i3.4490H26C···C9i3.2607
C10···H19v3.48 (2)H26C···H7Axv3.0971
C11···H21i3.4161H26C···H7Bxv2.5748
C11···H22i3.4272H26C···H8Ai3.3528
C12···H7Avii3.4446H26C···H9Ai2.6222
C12···H8Bvii3.2638H26C···H9Bi3.1600
C12···H14Bvi3.0435H26C···H26Aiv3.5872
C12···H23viii3.5857H18···O2v2.889 (17)
C13···H14Bvi3.1272H18···C5v3.406 (18)
C13···H21vii3.1484H18···C6v3.215 (18)
C14···H12Biii2.8748H18···C17v3.254 (18)
C14···H13Aiii3.3485H18···H13Bii2.9010
C14···H24iv3.5955H18···H17v2.4669
C14···H26Biv3.4019H19···O1i3.086 (19)
C15···H12Biii3.0475H19···C9i3.423 (19)
C15···H13Aiii3.3823H19···C10i3.48 (2)
C15···H13Biii3.2748H19···H9Ai2.6340
C15···H26Aiv3.1544H19···H14Aii3.4518
C15···H26Biv3.5549H19···H26Aiv3.5032
C10—O1—C11117.66 (10)C7—C8—H8A109.616
C25—O4—C26118.34 (13)C7—C8—H8B109.611
C6—C5—C10118.35 (13)C9—C8—H8A109.619
C6—C5—C17119.52 (11)C9—C8—H8B109.615
C10—C5—C17122.06 (12)H8A—C8—H8B108.140
O2—C6—C5120.97 (13)C8—C9—H9A109.512
O2—C6—C7122.05 (14)C8—C9—H9B109.511
C5—C6—C7116.91 (12)C10—C9—H9A109.516
C6—C7—C8112.29 (14)C10—C9—H9B109.524
C7—C8—C9110.21 (14)H9A—C9—H9B108.079
C8—C9—C10110.65 (12)C11—C12—H12A109.510
O1—C10—C5122.08 (13)C11—C12—H12B109.508
O1—C10—C9111.05 (11)C13—C12—H12A109.507
C5—C10—C9126.86 (14)C13—C12—H12B109.512
O1—C11—C12111.66 (11)H12A—C12—H12B108.072
O1—C11—C16122.96 (12)C12—C13—H13A109.490
C12—C11—C16125.36 (13)C12—C13—H13B109.492
C11—C12—C13110.69 (11)C14—C13—H13A109.484
C12—C13—C14110.77 (14)C14—C13—H13B109.490
C13—C14—C15114.19 (14)H13A—C13—H13B108.066
O3—C15—C14120.77 (14)C13—C14—H14A108.709
O3—C15—C16120.94 (13)C13—C14—H14B108.702
C14—C15—C16118.25 (12)C15—C14—H14A108.712
C11—C16—C15119.05 (12)C15—C14—H14B108.705
C11—C16—C17121.46 (12)H14A—C14—H14B107.635
C15—C16—C17119.49 (10)C5—C17—H17108.958
C5—C17—C16108.08 (9)C16—C17—H17108.950
C5—C17—C18112.10 (11)C18—C17—H17108.952
C16—C17—C18109.76 (10)C17—C18—H18114.8 (9)
C17—C18—C19124.37 (12)C19—C18—H18120.9 (9)
C18—C19—C20126.14 (13)C18—C19—H19118.2 (9)
C19—C20—C21122.58 (12)C20—C19—H19115.6 (9)
C19—C20—C25119.71 (12)C20—C21—H21119.284
C21—C20—C25117.70 (12)C22—C21—H21119.290
C20—C21—C22121.43 (14)C21—C22—H22120.210
C21—C22—C23119.59 (16)C23—C22—H22120.204
C22—C23—C24120.77 (16)C22—C23—H23119.611
C23—C24—C25119.54 (15)C24—C23—H23119.620
O4—C25—C20115.13 (12)C23—C24—H24120.229
O4—C25—C24123.89 (13)C25—C24—H24120.231
C20—C25—C24120.97 (14)O4—C26—H26A109.470
C6—C7—H7A109.148O4—C26—H26B109.470
C6—C7—H7B109.150O4—C26—H26C109.467
C8—C7—H7A109.145H26A—C26—H26B109.473
C8—C7—H7B109.144H26A—C26—H26C109.476
H7A—C7—H7B107.867H26B—C26—H26C109.471
C10—O1—C11—C12164.47 (9)C16—C11—C12—C1325.24 (18)
C10—O1—C11—C1614.26 (16)C11—C12—C13—C1450.00 (15)
C11—O1—C10—C513.16 (16)C12—C13—C14—C1549.61 (16)
C11—O1—C10—C9165.66 (9)C13—C14—C15—O3160.13 (13)
C26—O4—C25—C20174.47 (16)C13—C14—C15—C1622.03 (18)
C26—O4—C25—C244.6 (3)O3—C15—C16—C11172.68 (11)
C6—C5—C10—O1170.15 (10)O3—C15—C16—C177.37 (17)
C6—C5—C10—C98.47 (19)C14—C15—C16—C115.16 (17)
C10—C5—C6—O2178.59 (11)C14—C15—C16—C17174.80 (11)
C10—C5—C6—C71.71 (17)C11—C16—C17—C521.69 (15)
C6—C5—C17—C16154.19 (10)C11—C16—C17—C18100.83 (12)
C6—C5—C17—C1884.73 (13)C15—C16—C17—C5158.36 (10)
C17—C5—C6—O21.49 (18)C15—C16—C17—C1879.12 (13)
C17—C5—C6—C7175.39 (9)C5—C17—C18—C19129.02 (12)
C10—C5—C17—C1622.80 (15)C16—C17—C18—C19110.88 (13)
C10—C5—C17—C1898.28 (13)C17—C18—C19—C20177.35 (11)
C17—C5—C10—O16.88 (18)C18—C19—C20—C2126.5 (3)
C17—C5—C10—C9174.51 (10)C18—C19—C20—C25154.06 (13)
O2—C6—C7—C8148.51 (12)C19—C20—C21—C22179.46 (12)
C5—C6—C7—C834.64 (16)C19—C20—C25—O41.7 (2)
C6—C7—C8—C957.17 (15)C19—C20—C25—C24179.26 (12)
C7—C8—C9—C1046.59 (16)C21—C20—C25—O4178.83 (12)
C8—C9—C10—O1166.32 (12)C21—C20—C25—C240.2 (2)
C8—C9—C10—C514.9 (2)C25—C20—C21—C220.0 (2)
O1—C11—C12—C13156.06 (10)C20—C21—C22—C230.6 (3)
O1—C11—C16—C15175.32 (10)C21—C22—C23—C240.9 (3)
O1—C11—C16—C174.72 (18)C22—C23—C24—C250.7 (3)
C12—C11—C16—C153.24 (18)C23—C24—C25—O4179.08 (15)
C12—C11—C16—C17176.72 (11)C23—C24—C25—C200.1 (3)
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x1, y, z; (iii) x+1, y1/2, z+1/2; (iv) x, y+1, z; (v) x, y+1/2, z+1/2; (vi) x+1, y+1/2, z+1/2; (vii) x+1, y, z; (viii) x+1, y+3/2, z+1/2; (ix) x, y+1, z+1; (x) x, y+1/2, z+1/2; (xi) x1, y+1, z; (xii) x1, y+1/2, z+1/2; (xiii) x1, y+2, z; (xiv) x, y+3/2, z1/2; (xv) x, y+1/2, z1/2; (xvi) x1, y1/2, z+1/2; (xvii) x, y+3/2, z+1/2; (xviii) x1, y+3/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14B···O2vii0.972.433.3231 (18)153
Symmetry code: (vii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC22H22O4
Mr350.41
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.5396 (5), 9.9243 (7), 21.9501 (13)
β (°) 102.5455 (14)
V3)1815.85 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Rigaku, 1995)
Tmin, Tmax0.821, 0.983
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
17353, 4100, 3248
Rint0.018
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.136, 1.08
No. of reflections4100
No. of parameters244
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.21

Computer programs: RAPID-AUTO (Rigaku, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14B···O2i0.9702.43013.3231 (18)153
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

References

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First citationFun, H.-K., Loh, W.-S., Rajesh, K., Vijayakumar, V. & Sarveswari, S. (2011). Acta Cryst. E67, o1876–o1877.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationMehdi, S. H., Sulaiman, O., Ghalib, R. M., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1719–o1720.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationRigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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