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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2′-Carb­­oxy­meth­­oxy-4,4′-bis­­(3-methyl­but-2-en­yl­oxy)chalcone

aTianjin University of Commerce, Tianjin 300134, People's Republic of China, bSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China, and cTianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
*Correspondence e-mail: liudk@tjipr.com

(Received 28 February 2011; accepted 4 March 2011; online 9 March 2011)

In the title compound, C27H30O6, also known as sofalcone, an anti-ulcer agent used for the protection of gastric mucosa­, the two benzene rings form a dihedral angle of 6.78 (11)°. Inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers, which are further linked by weak C—H⋯O inter­actions into ribbons propagated in [2[\overline{1}]0]. Finally, ππ inter­actions between the benzene rings [centroid–centroid distance = 3.583 (13) Å] stabilize the crystal packing.

Related literature

For background to the bioactivity and applications of the title compound, see: Tanaka et al. (2009[Tanaka, H., Nakamura, S., Onda, K., Tazaki, T. & Hirano, T. (2009). Biochem. Biophys. Res. Commun. 383, 566-571.]). For a related structure, see: Cheng et al. (2007[Cheng, D., Liu, M., Liu, D.-K., Liu, Y. & Liu, C.-X. (2007). Acta Cryst. E63, o4496.]). For the preparation of the title compound, see: Kyogoku et al. (1978[Kyogoku, K., Hatayama, K., Yokomori, S., Sawada, J. & Tanaka, I. (1978). US Patent 4085135.], 1979[Kyogoku, K., Hatayama, K., Yokomori, S., Saziki, R., Nakane, S., Sasajima, M., Sawada, J., Ohzeki, M. & Tanaka, I. (1979). Chem. Pharm. Bull. 27, 2943-2953.]); Liu et al. (2009[Liu, Y., Liu, D. K., Liu, M., Huang, H. Z., Shuai, J., Yang, M., Zou, M. X. & Wu, J. (2009). CN Patent 101434533A.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C27H30O6

  • Mr = 450.51

  • Triclinic, [P \overline 1]

  • a = 7.4496 (15) Å

  • b = 12.195 (2) Å

  • c = 13.085 (3) Å

  • α = 88.39 (3)°

  • β = 78.53 (3)°

  • γ = 86.99 (3)°

  • V = 1163.3 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 113 K

  • 0.12 × 0.10 × 0.08 mm

Data collection
  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.989, Tmax = 0.993

  • 11767 measured reflections

  • 4097 independent reflections

  • 2371 reflections with I > 2σ(I)

  • Rint = 0.078

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.116

  • S = 0.92

  • 4097 reflections

  • 303 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 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
O4—H4⋯O3i 0.82 1.83 2.6474 (19) 176
C3—H3⋯O5ii 0.93 2.56 3.456 (2) 162
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+2, -y, -z+2.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound, (I), is a chalcone derivative also named sofalcone. It is an anti-ulcer agent used for the protection of gastric mucosa, although its precise molecular mechanism has not been completely understood (Tanaka et al., 2009). The crystal structrue of 1-[2-Hydroxy-4-(3-methylbut-2-enyloxy)-phenyl]ethan-1-one, an intermediate in the synthesis of sofalcone, has been reported by Cheng et al. (2007). Now, we present the crystal structure of the title compound.

In (I) (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). In the molecule, two benzene rings form a dihedral angle of 6.78 (11)°. Due to the p-π conjugation, the Csp2—O bonds [O1—C4 = 1.355 (2) Å and O6—C20 = 1.362 (2) Å] are significantly shorter than the Csp3—O bonds [O1—C7 = 1.441 (2) Å and O6—C23 = 1.442 (2) Å]. Intermolecular O—H···O hydrogen bonds link the molecules into centrosymmetric dimers, which are further linked by the weak C—H···O interactions into ribbons propagated in direction [2–10] (Table 1). Finally, π-π interactions between the benzene rings [centroid-to-centroid distance of 3.583 (13) Å] stabilize the crystal packing.

Related literature top

For background to the bioactivity and applications of the title compound, see: Tanaka et al. (2009). For a related structure, see: Cheng et al. (2007). For the preparation of the title compound, see: Kyogoku et al. (1978, 1979); Liu et al. (2009). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Several methods have been reported to prepare the title compound (Kyogoku et al., 1978; Kyogoku et al., 1979; Liu et al., 2009). Our experiment was carried out according to the method of Kyogoku et al. (1978) to get crude product as yellow powder. The powder (10 g) and activated carbon (1 g) were then dissolved in acetonitrile (80 ml) and the mixture was heated to reflux for 10 min. After filtration, the mixture was standing under room temperature for 24 h, then yellow crystals were generated slowly.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with d(C—H) = 0.93 - 0.97 Å and d(O—H) = 0.82 Å, and Uiso(H) = 1.2-1.5 Ueq of the parent atom.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids.
2-{5-[(3-methylbut-2-en-1-yl)oxy]-2-(3-{4-[(3-methylbut-2-en-1- yl)oxy]phenyl}prop-2-enoyl)phenoxy}acetic acid top
Crystal data top
C27H30O6Z = 2
Mr = 450.51F(000) = 480
Triclinic, P1Dx = 1.286 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4496 (15) ÅCell parameters from 3474 reflections
b = 12.195 (2) Åθ = 2.3–27.9°
c = 13.085 (3) ŵ = 0.09 mm1
α = 88.39 (3)°T = 113 K
β = 78.53 (3)°Prism, yellow
γ = 86.99 (3)°0.12 × 0.10 × 0.08 mm
V = 1163.3 (4) Å3
Data collection top
Rigaku Saturn
diffractometer
4097 independent reflections
Radiation source: rotating anode2371 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.078
ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
h = 88
Tmin = 0.989, Tmax = 0.993k = 1414
11767 measured reflectionsl = 1515
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0421P)2]
where P = (Fo2 + 2Fc2)/3
4097 reflections(Δ/σ)max < 0.001
303 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C27H30O6γ = 86.99 (3)°
Mr = 450.51V = 1163.3 (4) Å3
Triclinic, P1Z = 2
a = 7.4496 (15) ÅMo Kα radiation
b = 12.195 (2) ŵ = 0.09 mm1
c = 13.085 (3) ÅT = 113 K
α = 88.39 (3)°0.12 × 0.10 × 0.08 mm
β = 78.53 (3)°
Data collection top
Rigaku Saturn
diffractometer
4097 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
2371 reflections with I > 2σ(I)
Tmin = 0.989, Tmax = 0.993Rint = 0.078
11767 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 0.92Δρmax = 0.22 e Å3
4097 reflectionsΔρmin = 0.22 e Å3
303 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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) 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) top
xyzUiso*/Ueq
O10.45375 (16)0.07058 (11)1.21292 (10)0.0295 (4)
O20.39551 (15)0.25262 (10)1.01329 (10)0.0245 (3)
O30.19896 (16)0.42849 (11)0.96442 (10)0.0275 (4)
O40.04272 (16)0.38360 (11)1.08729 (10)0.0281 (4)
H40.08690.44221.06920.042*
O50.96148 (17)0.22153 (11)0.88715 (11)0.0325 (4)
O60.52436 (16)0.79502 (10)0.64049 (10)0.0290 (4)
C10.6943 (2)0.16654 (15)1.00089 (14)0.0206 (4)
C20.7978 (2)0.07896 (15)1.03331 (15)0.0232 (5)
H20.92310.07501.00590.028*
C30.7285 (2)0.00236 (16)1.10304 (14)0.0239 (5)
H30.80450.05911.12190.029*
C40.5426 (2)0.00300 (15)1.14398 (14)0.0225 (5)
C50.4324 (2)0.08869 (15)1.11472 (14)0.0228 (5)
H50.30750.09211.14290.027*
C60.5055 (2)0.16926 (15)1.04415 (14)0.0214 (5)
C70.5612 (3)0.16271 (16)1.24391 (16)0.0302 (5)
H7A0.66450.13751.27010.036*
H7B0.60750.20981.18500.036*
C80.4368 (3)0.22398 (16)1.32763 (15)0.0285 (5)
H80.31660.19631.34760.034*
C90.4851 (3)0.31441 (16)1.37529 (15)0.0291 (5)
C100.6741 (3)0.36753 (17)1.35051 (17)0.0428 (6)
H10A0.74730.32801.29410.064*
H10B0.66720.44211.33060.064*
H10C0.72900.36651.41090.064*
C110.3521 (3)0.37149 (18)1.45850 (16)0.0434 (6)
H11A0.23550.33161.46940.065*
H11B0.39770.37471.52220.065*
H11C0.33810.44471.43710.065*
C120.2107 (2)0.26291 (15)1.06756 (15)0.0234 (5)
H12A0.20650.26411.14210.028*
H12B0.14420.20081.05300.028*
C130.1247 (2)0.36717 (15)1.03284 (15)0.0223 (5)
C140.7976 (2)0.24378 (15)0.92286 (15)0.0222 (5)
C150.7105 (3)0.34591 (15)0.88957 (15)0.0250 (5)
H150.58960.36480.92020.030*
C160.8002 (3)0.41176 (15)0.81682 (15)0.0246 (5)
H160.92210.39140.78990.030*
C170.7269 (3)0.51316 (15)0.77462 (15)0.0238 (5)
C180.5463 (2)0.55068 (15)0.80792 (15)0.0265 (5)
H180.47150.51190.86050.032*
C190.4741 (3)0.64361 (16)0.76561 (15)0.0263 (5)
H190.35220.66650.78930.032*
C200.5842 (3)0.70289 (15)0.68747 (15)0.0237 (5)
C210.7656 (3)0.66794 (16)0.65364 (15)0.0267 (5)
H210.84060.70750.60170.032*
C220.8355 (3)0.57460 (16)0.69672 (15)0.0274 (5)
H220.95770.55210.67330.033*
C230.3328 (2)0.82802 (16)0.67028 (15)0.0291 (5)
H23A0.30080.84070.74470.035*
H23B0.25760.77100.65370.035*
C240.3013 (3)0.93145 (17)0.61086 (16)0.0361 (6)
H240.39690.95330.55830.043*
C250.1492 (3)0.99420 (16)0.62685 (15)0.0293 (5)
C260.1281 (3)1.09886 (17)0.56591 (17)0.0453 (7)
H26A0.23861.10960.51550.068*
H26B0.10481.15960.61260.068*
H26C0.02731.09420.53080.068*
C270.0158 (3)0.96821 (18)0.70712 (16)0.0382 (6)
H27A0.00930.90200.74420.057*
H27B0.11730.95840.67370.057*
H27C0.04571.02760.75520.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0232 (7)0.0239 (8)0.0385 (9)0.0037 (6)0.0028 (6)0.0157 (7)
O20.0173 (7)0.0230 (8)0.0315 (8)0.0048 (6)0.0031 (6)0.0071 (6)
O30.0187 (7)0.0253 (8)0.0359 (8)0.0027 (6)0.0011 (6)0.0096 (7)
O40.0198 (8)0.0236 (9)0.0375 (9)0.0061 (6)0.0010 (6)0.0096 (7)
O50.0204 (8)0.0287 (9)0.0441 (9)0.0042 (7)0.0007 (7)0.0110 (7)
O60.0252 (8)0.0252 (8)0.0331 (8)0.0073 (6)0.0015 (6)0.0106 (6)
C10.0188 (10)0.0176 (11)0.0252 (11)0.0017 (8)0.0048 (8)0.0007 (9)
C20.0160 (10)0.0222 (12)0.0310 (12)0.0007 (9)0.0045 (9)0.0023 (9)
C30.0254 (11)0.0167 (11)0.0299 (12)0.0042 (9)0.0086 (9)0.0053 (9)
C40.0251 (11)0.0180 (11)0.0242 (11)0.0012 (9)0.0051 (9)0.0046 (9)
C50.0186 (10)0.0224 (12)0.0267 (11)0.0023 (9)0.0045 (8)0.0034 (9)
C60.0233 (11)0.0168 (11)0.0251 (11)0.0044 (9)0.0089 (9)0.0011 (9)
C70.0318 (12)0.0213 (12)0.0367 (13)0.0062 (9)0.0081 (10)0.0077 (10)
C80.0327 (12)0.0244 (13)0.0274 (12)0.0007 (10)0.0041 (9)0.0008 (10)
C90.0424 (13)0.0218 (12)0.0242 (11)0.0040 (10)0.0089 (10)0.0018 (9)
C100.0554 (15)0.0256 (14)0.0482 (15)0.0045 (11)0.0152 (12)0.0100 (11)
C110.0607 (16)0.0346 (15)0.0361 (13)0.0087 (12)0.0123 (12)0.0117 (11)
C120.0157 (10)0.0236 (12)0.0295 (11)0.0020 (9)0.0024 (8)0.0024 (9)
C130.0166 (11)0.0220 (12)0.0285 (11)0.0006 (9)0.0055 (9)0.0012 (9)
C140.0221 (11)0.0182 (11)0.0264 (11)0.0005 (9)0.0059 (9)0.0014 (9)
C150.0215 (11)0.0206 (12)0.0319 (12)0.0015 (9)0.0042 (9)0.0044 (9)
C160.0216 (11)0.0211 (12)0.0300 (12)0.0025 (9)0.0036 (9)0.0023 (9)
C170.0260 (11)0.0196 (12)0.0256 (11)0.0007 (9)0.0054 (9)0.0020 (9)
C180.0253 (11)0.0220 (12)0.0304 (12)0.0001 (9)0.0032 (9)0.0081 (9)
C190.0217 (11)0.0237 (12)0.0316 (12)0.0019 (9)0.0023 (9)0.0045 (9)
C200.0288 (11)0.0182 (11)0.0242 (11)0.0019 (9)0.0062 (9)0.0021 (9)
C210.0276 (11)0.0243 (12)0.0264 (11)0.0000 (9)0.0023 (9)0.0056 (9)
C220.0221 (11)0.0256 (12)0.0322 (12)0.0030 (9)0.0016 (9)0.0029 (10)
C230.0243 (11)0.0261 (12)0.0334 (12)0.0071 (9)0.0000 (9)0.0065 (10)
C240.0302 (12)0.0335 (14)0.0387 (13)0.0049 (11)0.0032 (10)0.0158 (11)
C250.0268 (12)0.0255 (12)0.0344 (12)0.0021 (9)0.0048 (9)0.0081 (10)
C260.0361 (13)0.0385 (15)0.0585 (16)0.0036 (11)0.0067 (12)0.0212 (12)
C270.0306 (12)0.0448 (15)0.0375 (13)0.0069 (11)0.0061 (10)0.0074 (11)
Geometric parameters (Å, º) top
O1—C41.355 (2)C11—H11C0.9600
O1—C71.441 (2)C12—C131.494 (2)
O2—C61.374 (2)C12—H12A0.9700
O2—C121.419 (2)C12—H12B0.9700
O3—C131.215 (2)C14—C151.469 (3)
O4—C131.316 (2)C15—C161.326 (3)
O4—H40.8200C15—H150.9300
O5—C141.236 (2)C16—C171.464 (3)
O6—C201.362 (2)C16—H160.9300
O6—C231.442 (2)C17—C181.387 (2)
C1—C21.391 (2)C17—C221.396 (3)
C1—C61.407 (2)C18—C191.378 (3)
C1—C141.494 (3)C18—H180.9300
C2—C31.378 (3)C19—C201.389 (3)
C2—H20.9300C19—H190.9300
C3—C41.381 (2)C20—C211.384 (3)
C3—H30.9300C21—C221.380 (3)
C4—C51.387 (2)C21—H210.9300
C5—C61.385 (2)C22—H220.9300
C5—H50.9300C23—C241.496 (3)
C7—C81.497 (3)C23—H23A0.9700
C7—H7A0.9700C23—H23B0.9700
C7—H7B0.9700C24—C251.318 (3)
C8—C91.320 (3)C24—H240.9300
C8—H80.9300C25—C271.491 (3)
C9—C101.497 (3)C25—C261.504 (3)
C9—C111.501 (3)C26—H26A0.9600
C10—H10A0.9600C26—H26B0.9600
C10—H10B0.9600C26—H26C0.9600
C10—H10C0.9600C27—H27A0.9600
C11—H11A0.9600C27—H27B0.9600
C11—H11B0.9600C27—H27C0.9600
C4—O1—C7117.34 (14)O3—C13—C12124.87 (17)
C6—O2—C12117.60 (15)O4—C13—C12110.40 (16)
C13—O4—H4109.5O5—C14—C15119.55 (17)
C20—O6—C23117.28 (14)O5—C14—C1118.69 (17)
C2—C1—C6115.70 (17)C15—C14—C1121.75 (16)
C2—C1—C14115.69 (16)C16—C15—C14121.55 (17)
C6—C1—C14128.60 (17)C16—C15—H15119.2
C3—C2—C1124.82 (18)C14—C15—H15119.2
C3—C2—H2117.6C15—C16—C17126.66 (18)
C1—C2—H2117.6C15—C16—H16116.7
C2—C3—C4117.89 (18)C17—C16—H16116.7
C2—C3—H3121.1C18—C17—C22117.20 (18)
C4—C3—H3121.1C18—C17—C16121.73 (17)
O1—C4—C3125.01 (17)C22—C17—C16121.05 (17)
O1—C4—C5115.13 (16)C19—C18—C17122.12 (18)
C3—C4—C5119.87 (18)C19—C18—H18118.9
C6—C5—C4121.10 (17)C17—C18—H18118.9
C6—C5—H5119.4C18—C19—C20119.68 (18)
C4—C5—H5119.4C18—C19—H19120.2
O2—C6—C5121.04 (16)C20—C19—H19120.2
O2—C6—C1118.32 (17)O6—C20—C21116.85 (17)
C5—C6—C1120.63 (17)O6—C20—C19123.79 (17)
O1—C7—C8106.76 (15)C21—C20—C19119.37 (18)
O1—C7—H7A110.4C22—C21—C20120.17 (18)
C8—C7—H7A110.4C22—C21—H21119.9
O1—C7—H7B110.4C20—C21—H21119.9
C8—C7—H7B110.4C21—C22—C17121.45 (18)
H7A—C7—H7B108.6C21—C22—H22119.3
C9—C8—C7124.88 (19)C17—C22—H22119.3
C9—C8—H8117.6O6—C23—C24107.45 (15)
C7—C8—H8117.6O6—C23—H23A110.2
C8—C9—C10122.93 (19)C24—C23—H23A110.2
C8—C9—C11121.79 (19)O6—C23—H23B110.2
C10—C9—C11115.28 (18)C24—C23—H23B110.2
C9—C10—H10A109.5H23A—C23—H23B108.5
C9—C10—H10B109.5C25—C24—C23125.31 (18)
H10A—C10—H10B109.5C25—C24—H24117.3
C9—C10—H10C109.5C23—C24—H24117.3
H10A—C10—H10C109.5C24—C25—C27123.09 (19)
H10B—C10—H10C109.5C24—C25—C26122.65 (19)
C9—C11—H11A109.5C27—C25—C26114.26 (17)
C9—C11—H11B109.5C25—C26—H26A109.5
H11A—C11—H11B109.5C25—C26—H26B109.5
C9—C11—H11C109.5H26A—C26—H26B109.5
H11A—C11—H11C109.5C25—C26—H26C109.5
H11B—C11—H11C109.5H26A—C26—H26C109.5
O2—C12—C13108.73 (15)H26B—C26—H26C109.5
O2—C12—H12A109.9C25—C27—H27A109.5
C13—C12—H12A109.9C25—C27—H27B109.5
O2—C12—H12B109.9H27A—C27—H27B109.5
C13—C12—H12B109.9C25—C27—H27C109.5
H12A—C12—H12B108.3H27A—C27—H27C109.5
O3—C13—O4124.73 (17)H27B—C27—H27C109.5
C6—C1—C2—C30.1 (3)C6—C1—C14—O5173.38 (18)
C14—C1—C2—C3178.72 (18)C2—C1—C14—C15173.64 (17)
C1—C2—C3—C40.0 (3)C6—C1—C14—C157.9 (3)
C7—O1—C4—C31.5 (3)O5—C14—C15—C164.4 (3)
C7—O1—C4—C5178.51 (17)C1—C14—C15—C16176.88 (19)
C2—C3—C4—O1179.78 (18)C14—C15—C16—C17177.71 (18)
C2—C3—C4—C50.2 (3)C15—C16—C17—C180.9 (3)
O1—C4—C5—C6179.55 (17)C15—C16—C17—C22179.1 (2)
C3—C4—C5—C60.5 (3)C22—C17—C18—C191.0 (3)
C12—O2—C6—C59.4 (2)C16—C17—C18—C19177.29 (18)
C12—O2—C6—C1171.72 (16)C17—C18—C19—C200.4 (3)
C4—C5—C6—O2178.39 (17)C23—O6—C20—C21176.04 (16)
C4—C5—C6—C10.5 (3)C23—O6—C20—C193.7 (3)
C2—C1—C6—O2178.62 (16)C18—C19—C20—O6179.39 (18)
C14—C1—C6—O20.2 (3)C18—C19—C20—C210.4 (3)
C2—C1—C6—C50.3 (3)O6—C20—C21—C22179.27 (17)
C14—C1—C6—C5178.73 (19)C19—C20—C21—C220.5 (3)
C4—O1—C7—C8174.14 (16)C20—C21—C22—C170.1 (3)
O1—C7—C8—C9179.36 (18)C18—C17—C22—C210.8 (3)
C7—C8—C9—C100.1 (3)C16—C17—C22—C21177.45 (18)
C7—C8—C9—C11179.8 (2)C20—O6—C23—C24178.69 (16)
C6—O2—C12—C13171.66 (15)O6—C23—C24—C25170.7 (2)
O2—C12—C13—O34.4 (3)C23—C24—C25—C271.1 (3)
O2—C12—C13—O4175.26 (14)C23—C24—C25—C26178.5 (2)
C2—C1—C14—O55.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.821.832.6474 (19)176
C3—H3···O5ii0.932.563.456 (2)162
Symmetry codes: (i) x, y+1, z+2; (ii) x+2, y, z+2.

Experimental details

Crystal data
Chemical formulaC27H30O6
Mr450.51
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)7.4496 (15), 12.195 (2), 13.085 (3)
α, β, γ (°)88.39 (3), 78.53 (3), 86.99 (3)
V3)1163.3 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.12 × 0.10 × 0.08
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.989, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
11767, 4097, 2371
Rint0.078
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.116, 0.92
No. of reflections4097
No. of parameters303
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.22

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.821.832.6474 (19)176
C3—H3···O5ii0.932.563.456 (2)162
Symmetry codes: (i) x, y+1, z+2; (ii) x+2, y, z+2.
 

Acknowledgements

The authors thank Mr Hai-Bin Song at Nankai University for the X-ray measurements, structure determination and helpful suggestions.

References

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First citationKyogoku, K., Hatayama, K., Yokomori, S., Sawada, J. & Tanaka, I. (1978). US Patent 4085135.  Google Scholar
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First citationRigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTanaka, H., Nakamura, S., Onda, K., Tazaki, T. & Hirano, T. (2009). Biochem. Biophys. Res. Commun. 383, 566–571.  CrossRef Google Scholar

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