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ISSN: 2056-9890

Ethyl (Z)-4′-(4-eth­­oxy-1-hy­dr­oxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate

aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
*Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

(Received 28 June 2013; accepted 3 July 2013; online 10 July 2013)

The 1,3-diketone group of the title compound, C21H20O6, exists in a keto–enol form stabilized by a strong intra­molecular O—H⋯O hydrogen bond. As a result, a planar (mean deviation = 0.0099 Å) six-membered hydrogen-bonded ring is formed. The C—O and C—C bond lengths suggest significant electron delocalization in the ring. The dihedral angle between the six-membered hydrogen-bonded ring and its adjacent benzene ring is 8.78 (5)° and that between the benzene rings is 19.70 (5)°. In the crystal, mol­ecules are packed in a layered structure parallel to the b axis through C—H⋯O and ππ inter­actions [centroid–centroid distance between stacked benzene rings = 3.868 (2) Å].

Related literature

For background to this study, see: Ishikawa & Fujii (2011[Ishikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221-225.]). For related structures, see: Wang et al. (2008[Wang, J., Zhou, W. & Xu, W.-G. (2008). Acta Cryst. E64, o15.]); Pillay et al. (2013[Pillay, A., Khorasani, S. & de Koning, C. B. (2013). Acta Cryst. E69, o54-o55.]). For the biological activity of related compounds, see: Tomassini et al. (1994[Tomassini, J., Selnick, H., Davies, M. E., Armstrong, M. E., Baldwin, J., Bourgeois, M., Hastings, J., Hazuda, D., Lewis, J., McClements, W., Ponticello, G., Radzilowski, E., Smith, G., Tebben, A. & Wolfe, A. (1994). Antimicrob. Agents Chemother. 38, 2827-2837.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20O6

  • Mr = 368.39

  • Monoclinic, C 2/c

  • a = 26.572 (16) Å

  • b = 12.194 (5) Å

  • c = 11.213 (6) Å

  • β = 96.03 (5)°

  • V = 3613 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.50 × 0.45 × 0.30 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.707, Tmax = 0.971

  • 4944 measured reflections

  • 4109 independent reflections

  • 2874 reflections with F2 > 2σ(F2)

  • Rint = 0.029

  • 3 standard reflections every 150 reflections intensity decay: 0.7%

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.104

  • S = 1.01

  • 4109 reflections

  • 250 parameters

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

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H14⋯O4 0.98 (3) 1.61 (3) 2.522 (2) 152 (3)

Data collection: WinAFC (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC; data reduction: WinAFC; program(s) used to solve structure: SIR2008 (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); 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

Biphenyl diketo acids are known to inhibit influenza virus endonuclease (Tomassini et al. 1994). According to our inhibitor design targeting this metalloenzyme (Ishikawa et al. 2011), we synthesized the title compound by Claisen condensation of ethyl 4'-acetyl-[1,1'-biphenyl]-3-carboxylate with diethyl oxalate in the presence of sodium ethoxide, which biphenyl derivatives are the synthetic intermediates of a final biphenyl diketo acid. The 1,3-diketone group exists in keto-enol form stabilized by an intramolecular O–H···O hydrogen bond [O3···O4, 2.522 (2) Å, Table 1], as shown in Figure 1. The distances of C–O [C16–O3 = 1.3063 (18) Å, C18–O4 = 1.2736 (19) Å] and C–C bonds [C16–C17 = 1.403 (2) Å, C17–C18 = 1.396 (3) Å] in the 1,3-diketone group indicate charge delocalization among the atoms. As a result, a six-membered ring formed is essentially plane (mean deviation = 0.0099 Å). The dihedral angles between the six-membered ring and its adjacent benzene ring and between the two benzene rings are 8.78 (5) and 19.70 (5)°, respectively. In the crystal, the molecules are packed as a layered structure through intermolecular C–H···O and π···π interactions, as shown in Figure 2.

Related literature top

For background to this study, see: Ishikawa & Fujii (2011). For related structures, see: Wang et al. (2008); Pillay et al. (2013). For the biological activity of related compounds, see: Tomassini et al. (1994).

Experimental top

4'-Acetyl-[1,1'-biphenyl]-3-carboxylate (3.9 mmol), diethyl oxalate (4.7 mmol) and sodium ethoxide (5.4 mmol) were dissolved in ABS. THF (30 ml) and refluxed for 4 h. The reaction mixture was cooled to room temperature, and acidified with 2 M HCl (20 ml). After the mixture was extracted with ethyl acetate, the organic layer was washed with water and brine, and dried over anhydrous Mg2SO4. The title compound was obtained by column chromatography on silica gel (n-hexane: ethyl acetate = 3: 1, yield: 40%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate/n-hexane solution of the compound at room temperature.

Refinement top

The hydrogen atoms of phenyl ring were placed in geometrical positions [C–H 0.95 Å, Uiso(H) = 1.2Ueq(C)], and refined using a riding model. All hydrogen atoms of the vinyl, hydroxyl, methylene and methyl groups were found in a difference Fourier map, and refined using a riding model with distance constraint for the vinyl [C–H = 0.99 Å, Uiso(H) = 1.2Ueq(C)] and methylene H atoms [C–H = 0.95 Å, Uiso(H) = 1.2Ueq(C)]. A rotating group model was applied to the methyl groups with distance constraint [C–H = 0.98 Å, Uiso(H) = 1.2Ueq(C)]. The hydroxyl hydrogen was refined freely [O–H = 0.98 (3) Å].

Computing details top

Data collection: WinAFC (Rigaku, 1999); cell refinement: WinAFC (Rigaku, 1999); data reduction: WinAFC (Rigaku, 1999); program(s) used to solve structure: SIR2008 (Burla et al., 2007); 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 the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A crystal packing view of the title compound.
Ethyl (Z)-4'-(4-ethoxy-1-hydroxy-3,4-dioxobut-1-en-1-yl)-[1,1'-biphenyl]-3-carboxylate top
Crystal data top
C21H20O6F(000) = 1552.00
Mr = 368.39Dx = 1.354 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 26.572 (16) Åθ = 15.3–17.3°
b = 12.194 (5) ŵ = 0.10 mm1
c = 11.213 (6) ÅT = 100 K
β = 96.03 (5)°Block, yellow
V = 3613 (4) Å30.50 × 0.45 × 0.30 mm
Z = 8
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.029
ω scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 3434
Tmin = 0.707, Tmax = 0.971k = 015
4944 measured reflectionsl = 148
4109 independent reflections3 standard reflections every 150 reflections
2874 reflections with F2 > 2σ(F2) intensity decay: 0.7%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0448P)2 + 1.6001P]
where P = (Fo2 + 2Fc2)/3
4109 reflections(Δ/σ)max < 0.001
250 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.22 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C21H20O6V = 3613 (4) Å3
Mr = 368.39Z = 8
Monoclinic, C2/cMo Kα radiation
a = 26.572 (16) ŵ = 0.10 mm1
b = 12.194 (5) ÅT = 100 K
c = 11.213 (6) Å0.50 × 0.45 × 0.30 mm
β = 96.03 (5)°
Data collection top
Rigaku AFC-7R
diffractometer
2874 reflections with F2 > 2σ(F2)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.029
Tmin = 0.707, Tmax = 0.9713 standard reflections every 150 reflections
4944 measured reflections intensity decay: 0.7%
4109 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.25 e Å3
4109 reflectionsΔρmin = 0.22 e Å3
250 parameters
Special details top

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
O10.46554 (4)0.31724 (9)0.39851 (9)0.0275 (3)
O20.42694 (4)0.17877 (9)0.31120 (9)0.0273 (3)
O30.23852 (4)0.18855 (8)0.31124 (9)0.0240 (3)
O40.17956 (4)0.23322 (8)0.46659 (9)0.0245 (3)
O50.15319 (4)0.51499 (8)0.46408 (10)0.0278 (3)
O60.12949 (4)0.38111 (8)0.58408 (9)0.0234 (3)
C10.35694 (5)0.41174 (11)0.10207 (12)0.0193 (3)
C20.37847 (5)0.33352 (12)0.17183 (12)0.0198 (3)
C30.40986 (5)0.36425 (12)0.25797 (12)0.0212 (3)
C40.41931 (6)0.47473 (12)0.27835 (13)0.0249 (4)
C50.39742 (6)0.55328 (12)0.21089 (14)0.0260 (4)
C60.36726 (5)0.52305 (12)0.12270 (13)0.0231 (3)
C70.32531 (5)0.37938 (11)0.00602 (12)0.0183 (3)
C80.32783 (5)0.27412 (11)0.04357 (13)0.0218 (3)
C90.29951 (5)0.24567 (11)0.13554 (13)0.0221 (3)
C100.26788 (5)0.32256 (11)0.18255 (12)0.0194 (3)
C110.26469 (5)0.42780 (11)0.13267 (13)0.0216 (3)
C120.29254 (5)0.45500 (11)0.03963 (13)0.0219 (3)
C130.51901 (6)0.30330 (15)0.55382 (14)0.0340 (4)
C140.49283 (6)0.23779 (13)0.46382 (14)0.0291 (4)
C150.43394 (5)0.27607 (12)0.32420 (12)0.0213 (3)
C160.23830 (5)0.29209 (11)0.28132 (12)0.0195 (3)
C170.21060 (5)0.36805 (11)0.34202 (12)0.0201 (3)
C180.18231 (5)0.33257 (12)0.43284 (13)0.0202 (3)
C190.15335 (5)0.42051 (11)0.49450 (12)0.0203 (3)
C200.10152 (6)0.46341 (12)0.64510 (14)0.0265 (4)
C210.07504 (6)0.40539 (14)0.73898 (14)0.0297 (4)
H10.37160.25800.16040.0238*
H20.44050.49590.33760.0299*
H30.40310.62880.22530.0312*
H40.35340.57800.07570.0277*
H50.28940.52640.00590.0263*
H60.24320.48090.16300.0259*
H70.30160.17330.16700.0265*
H80.34940.22100.01350.0262*
H9C0.53930.25400.59860.0408*
H10B0.54110.35820.51160.0408*
H11A0.49360.34010.60960.0408*
H12A0.46910.18400.50520.0350*
H13B0.51790.19780.40850.0350*
H140.2155 (10)0.182 (3)0.374 (3)0.093 (9)*
H150.21110.44360.32140.0242*
H16B0.07650.50050.58700.0318*
H17A0.12500.51940.68290.0318*
H18A0.05090.35230.70030.0356*
H19B0.05690.45910.78350.0356*
H20C0.10000.36690.79440.0356*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0321 (6)0.0274 (6)0.0253 (6)0.0054 (5)0.0144 (5)0.0032 (5)
O20.0332 (6)0.0216 (6)0.0288 (6)0.0009 (5)0.0111 (5)0.0018 (5)
O30.0289 (6)0.0146 (5)0.0300 (6)0.0008 (5)0.0104 (5)0.0027 (5)
O40.0312 (6)0.0165 (5)0.0272 (6)0.0002 (4)0.0094 (5)0.0034 (4)
O50.0335 (6)0.0162 (6)0.0359 (6)0.0007 (5)0.0139 (5)0.0015 (5)
O60.0283 (6)0.0197 (5)0.0237 (6)0.0009 (5)0.0098 (5)0.0004 (4)
C10.0192 (7)0.0195 (7)0.0191 (7)0.0011 (6)0.0023 (6)0.0012 (6)
C20.0226 (7)0.0175 (7)0.0194 (7)0.0020 (6)0.0024 (6)0.0002 (6)
C30.0224 (7)0.0227 (8)0.0188 (7)0.0020 (6)0.0031 (6)0.0001 (6)
C40.0262 (8)0.0257 (8)0.0237 (7)0.0037 (6)0.0071 (6)0.0031 (6)
C50.0312 (8)0.0173 (7)0.0304 (8)0.0027 (6)0.0068 (7)0.0036 (6)
C60.0255 (8)0.0179 (7)0.0262 (8)0.0006 (6)0.0045 (6)0.0002 (6)
C70.0204 (7)0.0156 (7)0.0190 (7)0.0014 (6)0.0027 (6)0.0004 (6)
C80.0258 (8)0.0157 (7)0.0249 (8)0.0021 (6)0.0071 (6)0.0011 (6)
C90.0264 (8)0.0145 (7)0.0259 (8)0.0000 (6)0.0050 (6)0.0017 (6)
C100.0201 (7)0.0171 (7)0.0211 (7)0.0022 (6)0.0033 (6)0.0004 (6)
C110.0229 (7)0.0166 (7)0.0260 (8)0.0014 (6)0.0056 (6)0.0008 (6)
C120.0258 (8)0.0157 (7)0.0247 (8)0.0010 (6)0.0048 (6)0.0028 (6)
C130.0285 (9)0.0509 (11)0.0240 (8)0.0059 (8)0.0092 (7)0.0023 (8)
C140.0311 (9)0.0330 (9)0.0248 (8)0.0032 (7)0.0101 (7)0.0076 (7)
C150.0226 (7)0.0236 (8)0.0179 (7)0.0040 (6)0.0030 (6)0.0006 (6)
C160.0197 (7)0.0167 (7)0.0221 (7)0.0023 (6)0.0019 (6)0.0006 (6)
C170.0236 (7)0.0143 (7)0.0234 (7)0.0018 (6)0.0065 (6)0.0022 (6)
C180.0203 (7)0.0189 (7)0.0213 (7)0.0009 (6)0.0014 (6)0.0003 (6)
C190.0205 (7)0.0197 (7)0.0206 (7)0.0030 (6)0.0023 (6)0.0008 (6)
C200.0306 (8)0.0222 (8)0.0282 (8)0.0010 (6)0.0105 (7)0.0041 (6)
C210.0311 (9)0.0333 (9)0.0256 (8)0.0030 (7)0.0070 (7)0.0047 (7)
Geometric parameters (Å, º) top
O1—C141.453 (2)C16—C171.403 (2)
O1—C151.3410 (19)C17—C181.396 (3)
O2—C151.2122 (19)C18—C191.527 (2)
O3—C161.3063 (18)C20—C211.503 (3)
O4—C181.2736 (19)O3—H140.98 (3)
O5—C191.2014 (18)C2—H10.950
O6—C191.3325 (19)C4—H20.950
O6—C201.461 (2)C5—H30.950
C1—C21.394 (2)C6—H40.950
C1—C61.409 (2)C8—H80.950
C1—C71.487 (3)C9—H70.950
C2—C31.392 (3)C11—H60.950
C3—C41.394 (3)C12—H50.950
C3—C151.489 (2)C13—H9C0.980
C4—C51.386 (3)C13—H10B0.980
C5—C61.387 (3)C13—H11A0.980
C7—C81.398 (2)C14—H12A0.990
C7—C121.401 (2)C14—H13B0.990
C8—C91.383 (3)C17—H150.950
C9—C101.399 (2)C20—H16B0.990
C10—C111.399 (2)C20—H17A0.990
C10—C161.471 (3)C21—H18A0.980
C11—C121.381 (3)C21—H19B0.980
C13—C141.513 (3)C21—H20C0.980
O1···C42.713 (2)C13···H2viii2.9857
O2···C22.843 (2)C13···H3viii3.4897
O2···C142.672 (3)C13···H3vii3.5519
O3···O42.522 (2)C13···H18Aii3.0176
O3···C92.768 (3)C13···H18Aix3.5234
O3···C182.757 (2)C13···H20Cix3.5510
O4···O53.506 (2)C14···H18Aii2.9897
O4···O62.6695 (18)C15···H13Bi2.9416
O4···C162.819 (3)C16···H1ii3.1478
O5···C172.802 (2)C16···H5vi3.5161
O5···C202.643 (3)C17···H1ii3.2167
C1···C42.816 (3)C17···H5vi2.9340
C2···C52.770 (3)C17···H17Avii3.0634
C2···C82.975 (3)C18···H1ii3.4183
C3···C62.774 (3)C18···H5vi3.3520
C6···C122.950 (3)C18···H14iv3.30 (3)
C7···C102.821 (3)C18···H17Avii3.5401
C8···C112.771 (3)C19···H6vi3.1253
C9···C122.769 (3)C19···H12Aii3.5092
C11···C172.969 (3)C19···H17Avii3.5716
O1···C15i3.496 (3)C20···H7iv3.5648
O2···O4ii3.341 (3)C20···H12Aii2.9325
O2···O5ii3.505 (2)C20···H15vi3.5299
O2···O6ii3.344 (3)C21···H3iii3.4284
O2···C18ii3.078 (3)C21···H7iv3.4721
O2···C19ii3.053 (3)C21···H8iv3.5970
O2···C20iii3.352 (3)C21···H9Cx2.8914
O2···C21iii3.432 (3)C21···H12Aii2.9651
O3···O4iv3.273 (3)C21···H18Axi3.5436
O3···C1ii3.490 (3)C21···H19Bxi3.5504
O3···C2ii3.340 (3)H1···O3ii3.2877
O3···C11iii3.244 (2)H1···O4ii3.5590
O3···C12iii3.446 (2)H1···C16ii3.1478
O3···C18iv3.385 (3)H1···C17ii3.2167
O4···O2ii3.341 (3)H1···C18ii3.4183
O4···O3iv3.273 (3)H1···H9Ci3.5497
O4···C2ii3.591 (3)H1···H10Bi3.1063
O4···C3ii3.371 (3)H1···H13Bi3.0453
O4···C6iii3.411 (2)H1···H14ii3.2330
O4···C12iii3.475 (3)H1···H16Biii3.4926
O4···C15ii3.263 (3)H1···H17Aiii2.9232
O4···C16iv3.399 (3)H2···C6vii3.5703
O5···O2ii3.505 (2)H2···C13viii2.9857
O5···C8v3.202 (2)H2···H2i3.5455
O5···C9v3.322 (2)H2···H4vii3.4624
O5···C11vi3.415 (3)H2···H9Cviii3.1920
O5···C21vii3.244 (3)H2···H10Bviii2.5369
O6···O2ii3.344 (3)H2···H11Aviii2.7640
C1···O3ii3.490 (3)H2···H11Avi3.4310
C2···O3ii3.340 (3)H3···C7vii3.5820
C2···O4ii3.591 (3)H3···C8vii3.3219
C2···C13i3.537 (3)H3···C9vii3.3851
C2···C16ii3.561 (3)H3···C13viii3.4897
C3···O4ii3.371 (3)H3···C13vi3.5519
C6···O4v3.411 (2)H3···C21v3.4284
C8···O5iii3.202 (2)H3···H9Cviii2.9870
C8···C10ii3.596 (3)H3···H10Bviii3.4412
C9···O5iii3.322 (2)H3···H11Aviii3.4889
C10···C8ii3.596 (3)H3···H11Avi2.6355
C11···O3v3.244 (2)H3···H18Av2.9882
C11···O5vii3.415 (3)H3···H20Cv3.0038
C12···O3v3.446 (2)H4···O4v2.4644
C12···O4v3.475 (3)H4···C10vii3.5624
C13···C2i3.537 (3)H4···H2vi3.4624
C15···O1i3.496 (3)H4···H14v3.3091
C15···O4ii3.263 (3)H5···O3v2.9972
C15···C18ii3.463 (3)H5···O4v2.6608
C16···O4iv3.399 (3)H5···C16vii3.5161
C16···C2ii3.561 (3)H5···C17vii2.9340
C18···O2ii3.078 (3)H5···C18vii3.3520
C18···O3iv3.385 (3)H5···H14v2.3365
C18···C15ii3.463 (3)H5···H15vii2.8002
C19···O2ii3.053 (3)H6···O3v2.5881
C20···O2v3.352 (3)H6···O5vii3.0949
C21···O2v3.432 (3)H6···O6vii3.4902
C21···O5vi3.244 (3)H6···C19vii3.1253
O1···H22.3982H6···H7v3.3205
O1···H9C3.2233H6···H14v2.7309
O1···H10B2.5354H6···H17Avii3.1715
O1···H11A2.5700H7···O5iii2.7758
O2···H12.5449H7···O6iv3.2419
O2···H12A2.5507H7···C12ii3.5853
O2···H13B2.7648H7···C20iv3.5648
O3···H72.4545H7···C21iv3.4721
O3···H153.1988H7···H6iii3.3205
O4···H141.61 (3)H7···H15iii2.8263
O4···H153.1969H7···H17Aiv3.3859
O5···H152.4907H7···H20Civ2.6507
O5···H16B2.5829H8···O5iii2.5269
O5···H17A2.6402H8···C21iv3.5970
O6···H18A2.5990H8···H9Ci3.0378
O6···H19B3.2448H8···H10Bi3.3570
O6···H20C2.5671H8···H16Biii3.5833
C1···H33.2829H8···H17Aiii3.4169
C1···H52.6641H8···H20Civ2.6434
C1···H82.6798H9C···C8i3.5293
C2···H23.2759H9C···C21ix2.8914
C2···H43.2622H9C···H1i3.5497
C2···H82.6707H9C···H2viii3.1920
C3···H33.2539H9C···H3viii2.9870
C4···H13.2700H9C···H8i3.0378
C4···H43.2636H9C···H11Axii3.4602
C6···H13.2632H9C···H18Aii2.8535
C6···H23.2687H9C···H18Aix2.6475
C6···H52.6431H9C···H19Bix2.9744
C7···H12.6736H9C···H20Cix2.5743
C7···H42.6748H10B···C1i2.9426
C7···H63.2793H10B···C2i2.8215
C7···H73.2765H10B···C3i3.1638
C8···H12.6799H10B···C4viii3.3647
C8···H53.2553H10B···C6i3.3854
C9···H63.2652H10B···C7i3.5428
C10···H53.2666H10B···H1i3.1063
C10···H83.2685H10B···H2viii2.5369
C10···H143.18 (3)H10B···H3viii3.4412
C10···H152.7149H10B···H8i3.3570
C11···H73.2650H11A···C4viii3.5559
C11···H152.6786H11A···C4vii3.4333
C12···H42.6412H11A···C5vii2.9830
C12···H83.2562H11A···H2viii2.7640
C15···H12.6085H11A···H2vii3.4310
C15···H22.6912H11A···H3viii3.4889
C15···H12A2.5793H11A···H3vii2.6355
C15···H13B2.6884H11A···H9Cxii3.4602
C16···H62.6678H11A···H11Axii3.2029
C16···H72.6493H11A···H18Aii2.7724
C17···H62.6534H12A···O6ii2.7919
C17···H142.30 (3)H12A···C19ii3.5092
C18···H142.17 (3)H12A···C20ii2.9325
C19···H152.6130H12A···C21ii2.9651
C19···H16B2.5769H12A···H16Bii2.6725
C19···H17A2.6111H12A···H18Aii2.2402
H1···H82.1435H12A···H19Bii3.5794
H2···H32.3368H13B···O2i2.7405
H3···H42.3256H13B···C2i3.2567
H4···H52.1096H13B···C3i3.2453
H5···H62.3181H13B···C15i2.9416
H6···H152.0993H13B···H1i3.0453
H7···H82.3193H13B···H16Bxiii2.8690
H7···H143.4244H14···O4iv3.32 (3)
H9C···H12A2.3887H14···C2ii3.19 (3)
H9C···H13B2.3637H14···C3ii3.49 (3)
H10B···H12A2.8649H14···C11iii3.14 (3)
H10B···H13B2.3859H14···C12iii2.94 (3)
H11A···H12A2.3613H14···C18iv3.30 (3)
H11A···H13B2.8648H14···H1ii3.2330
H14···H153.2475H14···H4iii3.3091
H16B···H18A2.3503H14···H5iii2.3365
H16B···H19B2.3716H14···H6iii2.7309
H16B···H20C2.8545H15···C12vi3.3303
H17A···H18A2.8545H15···C20vii3.5299
H17A···H19B2.3484H15···H5vi2.8002
H17A···H20C2.3735H15···H7v2.8263
O2···H13Bi2.7405H15···H17Avii2.6640
O2···H16Biii3.3321H16B···O2v3.3321
O2···H17Aiii2.8585H16B···H1v3.4926
O2···H19Biii2.7254H16B···H8v3.5833
O3···H1ii3.2877H16B···H12Aii2.6725
O3···H5iii2.9972H16B···H13Bxiv2.8690
O3···H6iii2.5881H16B···H19Bvii3.4230
O4···H1ii3.5590H17A···O2v2.8585
O4···H4iii2.4644H17A···O5vi3.1902
O4···H5iii2.6608H17A···C17vi3.0634
O4···H14iv3.32 (3)H17A···C18vi3.5401
O5···H6vi3.0949H17A···C19vi3.5716
O5···H7v2.7758H17A···H1v2.9232
O5···H8v2.5269H17A···H6vi3.1715
O5···H17Avii3.1902H17A···H7iv3.3859
O5···H19Bvii3.1066H17A···H8v3.4169
O5···H20Cvii2.6696H17A···H15vi2.6640
O6···H6vi3.4902H18A···C13ii3.0176
O6···H7iv3.2419H18A···C13x3.5234
O6···H12Aii2.7919H18A···C14ii2.9897
C1···H10Bi2.9426H18A···C21xi3.5436
C2···H10Bi2.8215H18A···H3iii2.9882
C2···H13Bi3.2567H18A···H9Cii2.8535
C2···H14ii3.19 (3)H18A···H9Cx2.6475
C3···H10Bi3.1638H18A···H11Aii2.7724
C3···H13Bi3.2453H18A···H12Aii2.2402
C3···H14ii3.49 (3)H18A···H18Axi3.0315
C4···H10Bviii3.3647H18A···H19Bxi3.1694
C4···H11Aviii3.5559H19B···O2v2.7254
C4···H11Avi3.4333H19B···O5vi3.1066
C5···H11Avi2.9830H19B···C21xi3.5504
C6···H2vi3.5703H19B···H9Cx2.9744
C6···H10Bi3.3854H19B···H12Aii3.5794
C7···H3vi3.5820H19B···H16Bvi3.4230
C7···H10Bi3.5428H19B···H18Axi3.1694
C8···H3vi3.3219H19B···H19Bxi3.0404
C8···H9Ci3.5293H20C···O5vi2.6696
C8···H20Civ3.0334H20C···C8iv3.0334
C9···H3vi3.3851H20C···C9iv3.0310
C9···H20Civ3.0310H20C···C13x3.5510
C10···H4vi3.5624H20C···H3iii3.0038
C11···H14v3.14 (3)H20C···H7iv2.6507
C12···H7ii3.5853H20C···H8iv2.6434
C12···H14v2.94 (3)H20C···H9Cx2.5743
C12···H15vii3.3303
C14—O1—C15116.21 (13)C3—C2—H1119.466
C19—O6—C20114.27 (12)C3—C4—H2120.476
C2—C1—C6117.95 (14)C5—C4—H2120.481
C2—C1—C7121.42 (13)C4—C5—H3119.592
C6—C1—C7120.60 (13)C6—C5—H3119.564
C1—C2—C3121.08 (14)C1—C6—H4119.650
C2—C3—C4120.35 (14)C5—C6—H4119.663
C2—C3—C15118.15 (14)C7—C8—H8119.343
C4—C3—C15121.47 (14)C9—C8—H8119.332
C3—C4—C5119.04 (15)C8—C9—H7119.710
C4—C5—C6120.84 (14)C10—C9—H7119.736
C1—C6—C5120.69 (14)C10—C11—H6119.748
C1—C7—C8121.64 (13)C12—C11—H6119.758
C1—C7—C12120.66 (13)C7—C12—H5119.317
C8—C7—C12117.68 (14)C11—C12—H5119.315
C7—C8—C9121.33 (13)C14—C13—H9C109.471
C8—C9—C10120.55 (13)C14—C13—H10B109.472
C9—C10—C11118.55 (14)C14—C13—H11A109.458
C9—C10—C16120.26 (13)H9C—C13—H10B109.476
C11—C10—C16121.19 (13)H9C—C13—H11A109.476
C10—C11—C12120.49 (13)H10B—C13—H11A109.474
C7—C12—C11121.37 (13)O1—C14—H12A110.568
O1—C14—C13105.84 (14)O1—C14—H13B110.569
O1—C15—O2123.72 (14)C13—C14—H12A110.576
O1—C15—C3111.68 (13)C13—C14—H13B110.560
O2—C15—C3124.58 (14)H12A—C14—H13B108.723
O3—C16—C10116.68 (12)C16—C17—H15120.025
O3—C16—C17120.13 (13)C18—C17—H15120.024
C10—C16—C17123.19 (13)O6—C20—H16B110.178
C16—C17—C18119.95 (13)O6—C20—H17A110.180
O4—C18—C17124.30 (14)C21—C20—H16B110.180
O4—C18—C19119.08 (13)C21—C20—H17A110.180
C17—C18—C19116.62 (13)H16B—C20—H17A108.472
O5—C19—O6124.89 (14)C20—C21—H18A109.474
O5—C19—C18122.13 (14)C20—C21—H19B109.479
O6—C19—C18112.98 (12)C20—C21—H20C109.475
O6—C20—C21107.65 (13)H18A—C21—H19B109.468
C16—O3—H14106.3 (16)H18A—C21—H20C109.466
C1—C2—H1119.454H19B—C21—H20C109.466
C14—O1—C15—O21.11 (18)C12—C7—C8—H8179.2
C14—O1—C15—C3177.38 (10)C7—C8—C9—C100.80 (19)
C15—O1—C14—C13171.47 (10)C7—C8—C9—H7179.2
C15—O1—C14—H12A51.7H8—C8—C9—C10179.2
C15—O1—C14—H13B68.8H8—C8—C9—H70.8
H14—O3—C16—C10176.2 (15)C8—C9—C10—C111.45 (19)
H14—O3—C16—C173.5 (15)C8—C9—C10—C16179.30 (11)
C19—O6—C20—C21177.39 (10)H7—C9—C10—C11178.6
C19—O6—C20—H16B57.2H7—C9—C10—C160.7
C19—O6—C20—H17A62.4C9—C10—C11—C120.48 (19)
C20—O6—C19—O50.51 (18)C9—C10—C11—H6179.5
C20—O6—C19—C18179.85 (10)C9—C10—C16—O38.07 (18)
C2—C1—C6—C50.80 (18)C9—C10—C16—C17172.22 (11)
C2—C1—C6—H4179.2C11—C10—C16—O3171.16 (11)
C6—C1—C2—C31.00 (18)C11—C10—C16—C178.55 (19)
C6—C1—C2—H1179.0C16—C10—C11—C12179.72 (11)
C2—C1—C7—C819.70 (18)C16—C10—C11—H60.3
C2—C1—C7—C12161.64 (11)C10—C11—C12—C71.16 (19)
C7—C1—C2—C3177.12 (11)C10—C11—C12—H5178.8
C7—C1—C2—H12.9H6—C11—C12—C7178.8
C6—C1—C7—C8158.37 (11)H6—C11—C12—H51.2
C6—C1—C7—C1220.29 (18)H9C—C13—C14—O1177.7
C7—C1—C6—C5178.94 (11)H9C—C13—C14—H12A62.5
C7—C1—C6—H41.1H9C—C13—C14—H13B58.0
C1—C2—C3—C41.72 (19)H10B—C13—C14—O157.7
C1—C2—C3—C15176.49 (11)H10B—C13—C14—H12A177.5
H1—C2—C3—C4178.3H10B—C13—C14—H13B62.0
H1—C2—C3—C153.5H11A—C13—C14—O162.3
C2—C3—C4—C50.6 (2)H11A—C13—C14—H12A57.5
C2—C3—C4—H2179.4H11A—C13—C14—H13B178.0
C2—C3—C15—O1176.05 (11)O3—C16—C17—C181.40 (18)
C2—C3—C15—O22.42 (19)O3—C16—C17—H15178.6
C4—C3—C15—O12.14 (17)C10—C16—C17—C18178.29 (11)
C4—C3—C15—O2179.39 (12)C10—C16—C17—H151.7
C15—C3—C4—C5177.53 (11)C16—C17—C18—O40.2 (2)
C15—C3—C4—H22.5C16—C17—C18—C19179.90 (10)
C3—C4—C5—C61.2 (2)H15—C17—C18—O4179.8
C3—C4—C5—H3178.8H15—C17—C18—C190.1
H2—C4—C5—C6178.8O4—C18—C19—O5177.60 (11)
H2—C4—C5—H31.2O4—C18—C19—O63.04 (17)
C4—C5—C6—C11.9 (2)C17—C18—C19—O52.66 (18)
C4—C5—C6—H4178.1C17—C18—C19—O6176.70 (11)
H3—C5—C6—C1178.1O6—C20—C21—H18A62.1
H3—C5—C6—H41.9O6—C20—C21—H19B177.9
C1—C7—C8—C9177.89 (11)O6—C20—C21—H20C57.9
C1—C7—C8—H82.1H16B—C20—C21—H18A58.1
C1—C7—C12—C11176.92 (11)H16B—C20—C21—H19B61.9
C1—C7—C12—H53.1H16B—C20—C21—H20C178.1
C8—C7—C12—C111.78 (19)H17A—C20—C21—H18A177.7
C8—C7—C12—H5178.2H17A—C20—C21—H19B57.7
C12—C7—C8—C90.80 (19)H17A—C20—C21—H20C62.3
Symmetry codes: (i) x+1, y, z1/2; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y1/2, z+1/2; (iv) x+1/2, y+1/2, z+1; (v) x+1/2, y+1/2, z+1/2; (vi) x, y+1, z+1/2; (vii) x, y+1, z1/2; (viii) x+1, y+1, z1; (ix) x+1/2, y+1/2, z3/2; (x) x1/2, y+1/2, z+3/2; (xi) x, y, z+3/2; (xii) x+1, y, z3/2; (xiii) x+1/2, y1/2, z1; (xiv) x1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H14···O40.98 (3)1.61 (3)2.522 (2)152 (3)

Experimental details

Crystal data
Chemical formulaC21H20O6
Mr368.39
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)26.572 (16), 12.194 (5), 11.213 (6)
β (°) 96.03 (5)
V3)3613 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.50 × 0.45 × 0.30
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.707, 0.971
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
4944, 4109, 2874
Rint0.029
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.104, 1.01
No. of reflections4109
No. of parameters250
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.22

Computer programs: WinAFC (Rigaku, 1999), SIR2008 (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H14···O40.98 (3)1.61 (3)2.522 (2)152 (3)
 

Acknowledgements

This work was partly supported by Grants-in-Aid (No. 24590141 to YI) for Scientific Research from the Japan Society for the Promotion of Science. We acknowledge the University of Shizuoka for supporting this study.

References

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