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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 1| January 2013| Page o91
https://doi.org/10.1107/S1600536812050258

(E)-2-Hy­dr­oxy-4-meth­­oxy-3-(3-methyl­but-2-en­yl)-6-styryl­benzoic acid

Xingyue Ji,a Jie Jin,a Guanghui Zhenga and Zhuorong Lia*

aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China
*Correspondence e-mail: l-z-r@263.net

(Received 28 November 2012; accepted 10 December 2012; online 15 December 2012)

The title compound, C21H22O4, also known as cajanine, features an intra­molecular O—H⋯O hydrogen bond between the adjacent carb­oxy and hy­droxy groups. The benzene rings make an inter­planar angle of 175.4 (2)°. In the crystal, mol­ecules are linked by pairs of O—H⋯O hydrogen bonds, forming inversion dimers.

Related literature

Cajanine is an important component of the herb Cajanus cajan L., which is used in traditional Chinese medicine to treat osteonecrosis of the femoral head. For the total synthesis of cajanine, see: Ji et al. (2011[Ji, X.-Y., Xue, S.-T., Zheng, G.-H., Han, Y.-X., Liu, Z.-Y., Jiang, J.-D. & Li, Z.-R. (2011). Acta. Pharm. Sin. B, 1, 93-99.]). For the bioactivity of cajanine, see: Fu et al. (2009[Fu, Y.-J., Zhu, Y.-G., Wu, N., Kong, Y., Liu, W. & Hua, X. (2009). Chin. Patent CN 101485649.]); Ji et al. (2011[Ji, X.-Y., Xue, S.-T., Zheng, G.-H., Han, Y.-X., Liu, Z.-Y., Jiang, J.-D. & Li, Z.-R. (2011). Acta. Pharm. Sin. B, 1, 93-99.]); Luo et al. (2008a[Luo, Q.-F., Sun, L., Si, J.-Y. & Chen, D.-H. (2008a). Phytomedicine, 15, 932-939.],b[Luo, Q.-F., Sun, L., Si, J.-Y., Chen, D.-H. & Du, G.-H. (2008b). Yao Xue Xue Bao, 43, 145-149.]); Zheng et al. (2007a[Zheng, Y.-Y., Yang, J., Chen, D.-H. & Sun, L. (2007a). Yao Xue Xue Bao, 42, 386-391.],b[Zheng, Y.-Y., Yang, J., Chen, D.-H. & Sun, L. (2007b). Yao Xue Xue Bao, 42, 562-565.]); Inman & Hopp (2002[Inman, W. D. & Hopp, D. C. (2002). US Patent 20020058701A1.]); Ruan et al. (2009[Ruan, C.-J., Si, J.-Y., Zhang, L., Chen, D.-H., Du, G.-H. & Sun, L. (2009). Neurosci. Lett. 467, 159-63.]).

[Scheme 1]

Experimental

Crystal data

  • C21H22O4

  • Mr = 338.39

  • Triclinic, [P \overline 1]

  • a = 6.9790 (3) Å

  • b = 9.9975 (8) Å

  • c = 13.8202 (11) Å

  • α = 77.899 (1)°

  • β = 78.956 (2)°

  • γ = 78.507 (2)°

  • V = 912.58 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.35 × 0.32 × 0.31 mm
Data collection

  • Bruker SMART APEX diffractometer

  • 4547 measured reflections

  • 3138 independent reflections

  • 1735 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.152

  • S = 1.06

  • 3138 reflections

  • 229 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O2i 0.82 1.85 2.667 (2) 176
O3—H3⋯O2 0.82 1.82 2.546 (2) 147
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 1999[Bruker (1999). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SAINT and SMART. 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: SHELXTL (Sheldrick 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812050258/ng5309sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050258/ng5309Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812050258/ng5309Isup3.cml

checkCIF report


Comment top

Cajanine, also known as longistylineA-2-carboxylicacid, is a stilbene derivative isolated from the herb Cajanus cajan L. The herb has been used in traditional Chinese medicine for many years to treat osteonecrosis of the femoralhead. Cajanine is a good drug candidate because of its wide range of pharmacological activities, which include antitumor (Ji et al. 2011), anti- HSV (Fu et al. 2009), anti-hyperlipidemic (Luo et al., 2008a), anti-osteoporotic (Zheng et al., 2007a,b), hypoglycemic (Inman & Hopp, 2002) and antioxidant (Luo et al., 2008b) effects. It was also reported that cajanine can modulate Aβ25–35-induced cognitive deficits, oxidative stress and cholinergic dysfunction in mice (Ruan et al., 2009). We have accomplished its total synthesis previously (Ji et al. 2011), and the bioassay results showed that it showed some antiproliferative activity against human hepatoma cells.

The crystal structure of the title compound is reported here. In this crystal, the two benzene rings are not in the same plane, and the interplanar angle between them is 175.4 (2) °. A strong intramolecular O—H···O hydrogen bond is formed between the carboxyl group and a hydroxy group.

Related literature top

Cajanine is an important component of the herb Cajanus cajan L., which is used in traditional Chinese medicine to treat osteonecrosis of the femoral head. For the total synthesis of cajanine, see: Ji et al. (2011). For the bioactivity of cajanine, see: Fu et al. (2009); Ji et al. (2011); Luo et al. (2008a,b); Zheng et al. (2007a,b); Inman & Hopp (2002); Ruan et al. (2009).

Experimental top

(E)-Methyl 2-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-styrylbenzoate (0.5 g, 1.42 mmol) was dissolved in EtOH/H2O (15 ml/5 ml) and KOH (0.25 g, 4.26 mmol) was added. The mixture was heated under reflux for 3 h, and the reaction mixture was then added into ice water (50 ml) and the pH was adjusted to 2 with 10% HCl. The precipitate obtained was filtered and washed with water, dried in vacuum. The crude product was recrystallized from ethyl acetate / petroleum ether to give colorless crystals (0.38 g, 80%). m.p.168–170 °C.

1H NMR(400 MHz,CDCl3, 25 °C, TMS) δ: 11.58(s, 1H), 7.81(d, J = 16.0 Hz, 1H), 7.52(d, J = 7.2 Hz, 2H),7.38(t, J = 7.2 Hz,2H), 7.28(t, J = 7.2 Hz, 1H), 6.83(d, J = 16.0 Hz, 1H), 6.65(s, 1H), 5.22(t, J = 6.8 Hz, 1H), 3.95(s, 3H), 3.38(d, J = 6.8 Hz, 2H), 1.79(s, 3H), 1.68 (s, 3H), COOH was not observed. 13C NMR(100 MHz, CDCl3) δ: 174.95, 162.44, 162.25, 141.77, 137.28, 131.97, 130.86, 130.34, 128.74, 127.89, 126.79, 121.89, 116.77, 103.29, 102.97, 55.73, 25.82, 22.09, 17.80. HRMS(ESI) calcd for C21H22O4Na [M+Na]+ 361.14158, found 361.14318.

Refinement top

Hydrogens were generated geometrically.

Structure description top

Cajanine, also known as longistylineA-2-carboxylicacid, is a stilbene derivative isolated from the herb Cajanus cajan L. The herb has been used in traditional Chinese medicine for many years to treat osteonecrosis of the femoralhead. Cajanine is a good drug candidate because of its wide range of pharmacological activities, which include antitumor (Ji et al. 2011), anti- HSV (Fu et al. 2009), anti-hyperlipidemic (Luo et al., 2008a), anti-osteoporotic (Zheng et al., 2007a,b), hypoglycemic (Inman & Hopp, 2002) and antioxidant (Luo et al., 2008b) effects. It was also reported that cajanine can modulate Aβ25–35-induced cognitive deficits, oxidative stress and cholinergic dysfunction in mice (Ruan et al., 2009). We have accomplished its total synthesis previously (Ji et al. 2011), and the bioassay results showed that it showed some antiproliferative activity against human hepatoma cells.

The crystal structure of the title compound is reported here. In this crystal, the two benzene rings are not in the same plane, and the interplanar angle between them is 175.4 (2) °. A strong intramolecular O—H···O hydrogen bond is formed between the carboxyl group and a hydroxy group.

Cajanine is an important component of the herb Cajanus cajan L., which is used in traditional Chinese medicine to treat osteonecrosis of the femoral head. For the total synthesis of cajanine, see: Ji et al. (2011). For the bioactivity of cajanine, see: Fu et al. (2009); Ji et al. (2011); Luo et al. (2008a,b); Zheng et al. (2007a,b); Inman & Hopp (2002); Ruan et al. (2009).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 title molecule with the atom-numbering scheme. Ddisplacement parameters are shown at the 30% probability level.
[Figure 2] Fig. 2. Packing of the title molecules viewed along the a direction.
(E)-2-Hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-styrylbenzoic acid top
Crystal data top
C21H22O4Z = 2
Mr = 338.39F(000) = 360
Triclinic, P1Dx = 1.231 Mg m−3
a = 6.9790 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.9975 (8) ÅCell parameters from 1203 reflections
c = 13.8202 (11) Åθ = 2.8–25.6°
α = 77.899 (1)°µ = 0.08 mm−1
β = 78.956 (2)°T = 298 K
γ = 78.507 (2)°Lump, colorless
V = 912.58 (11) Å30.35 × 0.32 × 0.31 mm
Data collection top
Bruker SMART APEX
diffractometer		1735 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 25.0°, θmin = 3.0°
ω scansh = −8→8
4547 measured reflectionsk = −11→11
3138 independent reflectionsl = −16→12
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.057P)2 + 0.0883P]
where P = (Fo2 + 2Fc2)/3
3138 reflections(Δ/σ)max = 0.001
229 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C21H22O4γ = 78.507 (2)°
Mr = 338.39V = 912.58 (11) Å3
Triclinic, P1Z = 2
a = 6.9790 (3) ÅMo Kα radiation
b = 9.9975 (8) ŵ = 0.08 mm−1
c = 13.8202 (11) ÅT = 298 K
α = 77.899 (1)°0.35 × 0.32 × 0.31 mm
β = 78.956 (2)°
Data collection top
Bruker SMART APEX
diffractometer		1735 reflections with I > 2σ(I)
4547 measured reflectionsRint = 0.024
3138 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.06Δρmax = 0.15 e Å−3
3138 reflectionsΔρmin = −0.18 e Å−3
229 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
O10.8842 (3)0.47521 (18)0.39744 (12)0.0647 (5)
H10.96350.51500.41230.097*
O20.8460 (3)0.39954 (17)0.56073 (13)0.0578 (5)
O30.6238 (3)0.21943 (17)0.64005 (12)0.0622 (5)
H30.71000.26620.63620.093*
O40.1871 (3)0.12244 (19)0.45984 (13)0.0699 (6)
C10.7933 (3)0.4066 (2)0.47912 (19)0.0460 (6)
C20.6332 (3)0.3384 (2)0.46785 (17)0.0425 (6)
C30.5566 (3)0.2451 (2)0.55136 (17)0.0460 (6)
C40.4102 (3)0.1710 (2)0.54695 (18)0.0474 (6)
C50.3353 (4)0.1946 (3)0.45837 (19)0.0508 (7)
C60.4050 (4)0.2864 (2)0.37512 (18)0.0500 (6)
H60.35170.29920.31650.060*
C70.5533 (3)0.3596 (2)0.37766 (17)0.0442 (6)
C80.3312 (4)0.0732 (3)0.63820 (18)0.0568 (7)
H8A0.2964−0.00380.61640.068*
H8B0.43560.03580.67860.068*
C90.1559 (4)0.1381 (3)0.7015 (2)0.0639 (8)
H90.09230.22370.67230.077*
C100.0802 (5)0.0907 (3)0.7923 (2)0.0786 (9)
C110.1714 (8)−0.0452 (5)0.8471 (3)0.170 (2)
H11A0.1457−0.11930.81980.255*
H11B0.1155−0.05490.91680.255*
H11C0.3118−0.04850.84000.255*
C12−0.0985 (6)0.1646 (4)0.8487 (3)0.1287 (15)
H12A−0.13690.25470.81040.193*
H12B−0.06930.17450.91170.193*
H12C−0.20480.11240.86030.193*
C130.6113 (4)0.4597 (3)0.28730 (18)0.0516 (7)
H130.63500.54440.29600.062*
C140.6320 (4)0.4374 (3)0.1946 (2)0.0628 (8)
H140.61730.34980.18740.075*
C150.6759 (4)0.5363 (4)0.1019 (2)0.0683 (8)
C160.6483 (5)0.6766 (4)0.1000 (2)0.0940 (11)
H160.60440.71110.15930.113*
C170.6849 (7)0.7665 (5)0.0111 (3)0.1376 (17)
H170.66640.86130.01070.165*
C180.7484 (8)0.7173 (7)−0.0768 (4)0.139 (2)
H180.77030.7791−0.13670.167*
C190.7796 (6)0.5793 (7)−0.0771 (3)0.1203 (17)
H190.82730.5457−0.13660.144*
C200.7398 (5)0.4888 (4)0.0121 (2)0.0903 (11)
H200.75640.39430.01160.108*
C210.1162 (4)0.1248 (3)0.3689 (2)0.0719 (8)
H21A0.05090.21670.34550.108*
H21B0.02450.06100.38100.108*
H21C0.22570.09830.31910.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0679 (12)0.0791 (13)0.0572 (11)−0.0449 (10)−0.0144 (9)0.0008 (10)
O20.0604 (12)0.0644 (12)0.0567 (11)−0.0276 (9)−0.0195 (9)−0.0032 (9)
O30.0674 (12)0.0704 (12)0.0540 (11)−0.0300 (10)−0.0169 (9)0.0021 (9)
O40.0663 (13)0.0852 (14)0.0689 (13)−0.0438 (11)−0.0076 (10)−0.0106 (10)
C10.0412 (15)0.0437 (15)0.0537 (16)−0.0126 (12)−0.0063 (13)−0.0060 (12)
C20.0386 (14)0.0433 (14)0.0484 (14)−0.0123 (11)−0.0041 (11)−0.0114 (11)
C30.0459 (15)0.0477 (15)0.0452 (14)−0.0110 (12)−0.0071 (12)−0.0068 (12)
C40.0431 (15)0.0463 (15)0.0539 (15)−0.0160 (12)−0.0011 (12)−0.0089 (12)
C50.0436 (15)0.0542 (16)0.0600 (16)−0.0195 (13)−0.0015 (13)−0.0171 (13)
C60.0474 (15)0.0564 (16)0.0513 (15)−0.0165 (13)−0.0098 (12)−0.0119 (13)
C70.0400 (14)0.0453 (14)0.0491 (14)−0.0129 (11)−0.0039 (11)−0.0103 (12)
C80.0527 (17)0.0517 (16)0.0648 (17)−0.0180 (13)−0.0067 (14)−0.0014 (13)
C90.0547 (18)0.0699 (19)0.0581 (18)−0.0097 (15)−0.0068 (14)0.0062 (15)
C100.085 (2)0.092 (2)0.0524 (18)−0.0209 (19)−0.0035 (17)0.0007 (17)
C110.214 (5)0.129 (4)0.099 (3)0.012 (4)0.032 (3)0.041 (3)
C120.112 (3)0.169 (4)0.081 (3)−0.009 (3)0.022 (2)−0.016 (3)
C130.0487 (16)0.0574 (16)0.0534 (16)−0.0189 (13)−0.0129 (12)−0.0063 (13)
C140.0596 (18)0.075 (2)0.0587 (18)−0.0266 (15)−0.0070 (14)−0.0099 (15)
C150.0539 (18)0.102 (3)0.0540 (18)−0.0332 (17)−0.0130 (14)−0.0010 (17)
C160.110 (3)0.101 (3)0.068 (2)−0.039 (2)−0.0156 (19)0.015 (2)
C170.161 (4)0.140 (4)0.099 (3)−0.062 (3)−0.025 (3)0.045 (3)
C180.124 (4)0.208 (6)0.077 (3)−0.080 (4)−0.030 (3)0.055 (4)
C190.085 (3)0.221 (5)0.055 (2)−0.051 (4)−0.0123 (19)0.001 (3)
C200.075 (2)0.145 (3)0.056 (2)−0.038 (2)−0.0091 (16)−0.014 (2)
C210.0644 (19)0.083 (2)0.085 (2)−0.0313 (16)−0.0194 (16)−0.0250 (17)
Geometric parameters (Å, º) top
O1—C11.312 (3)C11—H11A0.9600
O1—H10.8200C11—H11B0.9600
O2—C11.236 (3)C11—H11C0.9600
O3—C31.352 (3)C12—H12A0.9600
O3—H30.8200C12—H12B0.9600
O4—C51.368 (3)C12—H12C0.9600
O4—C211.430 (3)C13—C141.322 (3)
C1—C21.467 (3)C13—H130.9300
C2—C31.414 (3)C14—C151.467 (4)
C2—C71.420 (3)C14—H140.9300
C3—C41.393 (3)C15—C161.372 (4)
C4—C51.379 (3)C15—C201.384 (4)
C4—C81.511 (3)C16—C171.375 (4)
C5—C61.387 (3)C16—H160.9300
C6—C71.391 (3)C17—C181.367 (6)
C6—H60.9300C17—H170.9300
C7—C131.472 (3)C18—C191.354 (6)
C8—C91.482 (4)C18—H180.9300
C8—H8A0.9700C19—C201.384 (5)
C8—H8B0.9700C19—H190.9300
C9—C101.294 (4)C20—H200.9300
C9—H90.9300C21—H21A0.9600
C10—C121.487 (4)C21—H21B0.9600
C10—C111.494 (5)C21—H21C0.9600
C1—O1—H1109.5C10—C11—H11C109.5
C3—O3—H3109.5H11A—C11—H11C109.5
C5—O4—C21119.8 (2)H11B—C11—H11C109.5
O2—C1—O1120.0 (2)C10—C12—H12A109.5
O2—C1—C2122.9 (2)C10—C12—H12B109.5
O1—C1—C2117.1 (2)H12A—C12—H12B109.5
C3—C2—C7118.5 (2)C10—C12—H12C109.5
C3—C2—C1117.8 (2)H12A—C12—H12C109.5
C7—C2—C1123.7 (2)H12B—C12—H12C109.5
O3—C3—C4115.6 (2)C14—C13—C7124.5 (2)
O3—C3—C2122.2 (2)C14—C13—H13117.8
C4—C3—C2122.2 (2)C7—C13—H13117.8
C5—C4—C3117.8 (2)C13—C14—C15126.9 (3)
C5—C4—C8121.7 (2)C13—C14—H14116.6
C3—C4—C8120.5 (2)C15—C14—H14116.6
O4—C5—C4115.0 (2)C16—C15—C20118.1 (3)
O4—C5—C6123.2 (2)C16—C15—C14122.2 (3)
C4—C5—C6121.7 (2)C20—C15—C14119.6 (3)
C5—C6—C7121.3 (2)C15—C16—C17120.5 (4)
C5—C6—H6119.4C15—C16—H16119.7
C7—C6—H6119.4C17—C16—H16119.7
C6—C7—C2118.5 (2)C18—C17—C16120.4 (5)
C6—C7—C13117.4 (2)C18—C17—H17119.8
C2—C7—C13124.0 (2)C16—C17—H17119.8
C9—C8—C4114.1 (2)C19—C18—C17120.4 (4)
C9—C8—H8A108.7C19—C18—H18119.8
C4—C8—H8A108.7C17—C18—H18119.8
C9—C8—H8B108.7C18—C19—C20119.2 (4)
C4—C8—H8B108.7C18—C19—H19120.4
H8A—C8—H8B107.6C20—C19—H19120.4
C10—C9—C8128.2 (3)C19—C20—C15121.3 (4)
C10—C9—H9115.9C19—C20—H20119.4
C8—C9—H9115.9C15—C20—H20119.4
C9—C10—C12123.6 (3)O4—C21—H21A109.5
C9—C10—C11120.6 (3)O4—C21—H21B109.5
C12—C10—C11115.8 (3)H21A—C21—H21B109.5
C10—C11—H11A109.5O4—C21—H21C109.5
C10—C11—H11B109.5H21A—C21—H21C109.5
H11A—C11—H11B109.5H21B—C21—H21C109.5
O2—C1—C2—C3−9.3 (3)C3—C2—C7—C6−0.8 (3)
O1—C1—C2—C3169.4 (2)C1—C2—C7—C6178.3 (2)
O2—C1—C2—C7171.6 (2)C3—C2—C7—C13176.3 (2)
O1—C1—C2—C7−9.7 (3)C1—C2—C7—C13−4.6 (4)
C7—C2—C3—O3−179.7 (2)C5—C4—C8—C9−86.0 (3)
C1—C2—C3—O31.1 (3)C3—C4—C8—C991.3 (3)
C7—C2—C3—C41.8 (3)C4—C8—C9—C10−165.1 (3)
C1—C2—C3—C4−177.4 (2)C8—C9—C10—C12−179.4 (3)
O3—C3—C4—C5179.4 (2)C8—C9—C10—C110.7 (6)
C2—C3—C4—C5−2.1 (3)C6—C7—C13—C14−41.1 (3)
O3—C3—C4—C81.9 (3)C2—C7—C13—C14141.8 (3)
C2—C3—C4—C8−179.5 (2)C7—C13—C14—C15175.4 (2)
C21—O4—C5—C4−171.9 (2)C13—C14—C15—C16−18.2 (5)
C21—O4—C5—C68.9 (4)C13—C14—C15—C20164.4 (3)
C3—C4—C5—O4−177.8 (2)C20—C15—C16—C17−0.5 (5)
C8—C4—C5—O4−0.4 (3)C14—C15—C16—C17−177.9 (3)
C3—C4—C5—C61.4 (4)C15—C16—C17—C180.4 (6)
C8—C4—C5—C6178.8 (2)C16—C17—C18—C19−1.3 (8)
O4—C5—C6—C7178.7 (2)C17—C18—C19—C202.3 (7)
C4—C5—C6—C7−0.4 (4)C18—C19—C20—C15−2.4 (6)
C5—C6—C7—C20.1 (3)C16—C15—C20—C191.5 (5)
C5—C6—C7—C13−177.2 (2)C14—C15—C20—C19179.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.852.667 (2)176
O3—H3···O20.821.822.546 (2)147
Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC21H22O4
Mr338.39
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)6.9790 (3), 9.9975 (8), 13.8202 (11)
α, β, γ (°)77.899 (1), 78.956 (2), 78.507 (2)
V (Å3)912.58 (11)
Z2
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.35 × 0.32 × 0.31
Data collection
DiffractometerBruker SMART APEX
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		4547, 3138, 1735
Rint0.024
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.152, 1.06
No. of reflections3138
No. of parameters229
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.15, −0.18

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.852.667 (2)176.3
O3—H3···O20.821.822.546 (2)147.0
Symmetry code: (i) −x+2, −y+1, −z+1.
 

Acknowledgements

This work was supported by the National S&T Major Special Project on Major New Drug Innovation (2012ZX09301002–001). We also thank Professor Su-na Wang at Liaocheng University for assistance with the crystallography and help with the X-ray experiment.

References

First citationBruker (1999). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFu, Y.-J., Zhu, Y.-G., Wu, N., Kong, Y., Liu, W. & Hua, X. (2009). Chin. Patent CN 101485649.  Google Scholar
 First citationInman, W. D. & Hopp, D. C. (2002). US Patent 20020058701A1.  Google Scholar
 First citationJi, X.-Y., Xue, S.-T., Zheng, G.-H., Han, Y.-X., Liu, Z.-Y., Jiang, J.-D. & Li, Z.-R. (2011). Acta. Pharm. Sin. B, 1, 93–99.  CrossRef CAS Google Scholar
 First citationLuo, Q.-F., Sun, L., Si, J.-Y. & Chen, D.-H. (2008a). Phytomedicine, 15, 932–939.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationLuo, Q.-F., Sun, L., Si, J.-Y., Chen, D.-H. & Du, G.-H. (2008b). Yao Xue Xue Bao, 43, 145-149.  PubMed Google Scholar
 First citationRuan, C.-J., Si, J.-Y., Zhang, L., Chen, D.-H., Du, G.-H. & Sun, L. (2009). Neurosci. Lett. 467, 159–63.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZheng, Y.-Y., Yang, J., Chen, D.-H. & Sun, L. (2007a). Yao Xue Xue Bao, 42, 386–391.  PubMed Google Scholar
 First citationZheng, Y.-Y., Yang, J., Chen, D.-H. & Sun, L. (2007b). Yao Xue Xue Bao, 42, 562–565.  PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 69| Part 1| January 2013| Page o91
https://doi.org/10.1107/S1600536812050258
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