Monoclinic, P2 1 =c a = (3) Å b = (3) Å c = (15) Å = (3) V = (5) Å 3. Data collection.

Transcription

1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Tectorigenin monohydrate: an isoflavone from Belamcanda chinensis Benguo Liu, a * Yuxiang Ma, b Han Gao a and Qiong Wu c a School of Food Science, Henan Institute of Science and Technology, Xinxiang , People s Republic of China, b College of Grain and Food, Henan University of Technology, Zhengzhou , People s Republic of China, and c Jilin Key Laboratory for Biotechnology of Agricultural Products Processing, Changchun University, Changchun , People s Republic of China Correspondence benguoliu2008@yahoo.com.cn Received 20 September 2008; accepted 24 September 2008 Monoclinic, P2 1 =c a = (3) Å b = (3) Å c = (15) Å = (3) V = (5) Å 3 Data collection Rigaku Saturn CCD area-detector diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T min = 0.973, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 224 parameters Z =4 Mo K radiation = 0.13 mm 1 T = 113 (2) K mm 9180 measured reflections 2967 independent reflections 2069 reflections with I > 2(I) R int = H atoms treated by a mixture of independent and constrained refinement max = 0.33 e Å 3 min = 0.27 e Å 3 Key indicators: single-crystal X-ray study; T = 113 K; mean (C C) = Å; R factor = 0.045; wr factor = 0.117; data-to-parameter ratio = Table 1 Hydrogen-bond geometry (Å, ). The title compound [systematic name: 5,7-dihydroxy-3-(4- hydroxyphenyl)-6-methoxy-4h-chromen-4-one monohydrate], C 16 H 12 O 6 H 2 O, is isolated from Belamcanda chinensis and is said to have antimicrobiotic and anti-inflammatory effects. The chromen-4-one system and the benzene ring are inclined at a dihedral angle of (6). Molecules are linked by interand intramolecular O HO hydrogen bonds. Related literature For general background, see: Oh et al. (2001). For a related structure, see: Gao et al. (2008). D HA D H HA DA D HA O7 H7BO2 i 0.77 (3) 2.57 (2) (2) 114 (2) O7 H7AO6 ii 0.95 (3) 1.95 (3) (2) 167 (2) O6 H6O1 iii 0.88 (2) 1.88 (2) (17) 167 (2) O3 H3O (2) 1.71 (2) (16) (18) O1 H1O7 iv 0.87 (2) 1.83 (2) (17) (19) Symmetry codes: (i) x; y; z þ 1; (ii) x 1; y þ 3 2 ; z 1 2 ; (iii) x þ 1; y; z þ 1; (iv) x; y; z 1. Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2795). Experimental Crystal data C 16 H 12 O 6 H 2 O M r = References Gao, H., Li, G., Zhang, J. & Zeng, J. (2008). Acta Cryst. E64, o1538. Oh, K. B., Kang, H. & Matsuoka, H. (2001). Biosci. Biotechnol. Biochem. 65, Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Sheldrick, G. M. (2008). Acta Cryst. A64, o2056 Liu et al. doi: /s

2 supporting information [doi: /s ] Tectorigenin monohydrate: an isoflavone from Belamcanda chinensis Benguo Liu, Yuxiang Ma, Han Gao and Qiong Wu S1. Comment The title compound [systematic name: 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one] was isolated from Belamcanda chinensis and is said to have antimicrobiotic and anti-inflammatory effects. We report here the crystal structure of its monohydrate. The two aromatic ring systems rings are inclined at a dihedral angle of (6). The molecules are linked by intermolecular O H O hydrogen bonds (Table 1). S2. Experimental The title compound was isolated from Belamcanda chinensis. S3. Refinement H atoms bonded to C were positioned geometrically (C H= Å), and refined as riding with U iso (H)=1.2U eq (C) or 1.5 eq (C methyl ). The coordinates of the H atoms bonded to O were refined with U iso (H)=1.5U eq (O). Figure 1 A view of the title compound. Displacement ellopsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. sup-1

3 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one monohydrate Crystal data C 16 H 12 O 6 H 2 O M r = Monoclinic, P2 1 /c Hall symbol: -P 2ybc a = (3) Å b = (3) Å c = (15) Å β = (3) V = (5) Å 3 Z = 4 Data collection Rigaku Saturn CCD area-detector diffractometer Radiation source: rotating anode Confocal monochromator Detector resolution: 7.31 pixels mm -1 ω and φ scans Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T min = 0.973, T max = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 224 parameters 0 restraints Primary atom site location: structure-invariant direct methods F(000) = 664 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 2562 reflections θ = µ = 0.13 mm 1 T = 113 K Block, colorless mm 9180 measured reflections 2967 independent reflections 2069 reflections with I > 2σ(I) R int = θ max = 27.1, θ min = 1.6 h = k = l = 9 7 Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H atoms treated by a mixture of independent and constrained refinement w = 1/[σ 2 (F o2 ) + (0.0629P) 2 ] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.33 e Å 3 Δρ min = 0.27 e Å 3 Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 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 (Å 2 ) x y z U iso */U eq O (10) (7) (17) (3) H (17) (14) (3) 0.031* O (9) (7) (16) (3) sup-2

4 O (10) (7) (17) (3) H (18) (13) (3) 0.029* O (9) (7) (17) (3) O (9) (7) (16) (3) O (10) (8) (18) (3) H (18) (15) (3) 0.033* C (13) (10) (2) (4) C (13) (9) (2) (4) H * C (13) (9) (2) (4) C (13) (10) (2) (4) H * C (13) (10) (2) (4) C (13) (10) (2) (4) C (13) (10) (2) (4) C (13) (9) (2) (4) C (14) (9) (2) (4) C (15) (11) (3) (5) H10A * H10B * H10C * C (13) (9) (2) (4) C (14) (9) (2) (4) H * C (14) (9) (2) (4) H * C (13) (10) (2) (4) C (14) (10) (2) (4) H * C (14) (10) (2) (4) H * O (12) (9) (2) (4) H7A (2) (15) (4) 0.050* H7B (2) (18) (4) 0.050* Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (7) (6) (7) (4) (5) (4) O (7) (5) (6) (4) (5) (4) O (7) (5) (7) (4) (5) (4) O (6) (5) (6) (4) (5) (4) O (6) (5) (6) (4) (5) (4) O (7) (6) (7) (5) (5) (4) C (8) (8) (8) (6) (7) (5) C (9) (7) (8) (6) (7) (5) C (8) (7) (8) (6) (7) (5) C (8) (7) (8) (6) (7) (5) sup-3

5 C (8) (7) (8) (6) (7) (5) C (9) (7) (8) (6) (7) (5) C (8) (7) (8) (6) (7) (5) C (9) (7) (8) (6) (7) (5) C (9) (7) (8) (6) (7) (5) C (10) (8) (10) (7) (8) (6) C (9) (7) (8) (6) (7) (5) C (9) (7) (8) (6) (7) (5) C (10) (7) (8) (6) (7) (5) C (8) (7) (8) (6) (7) (5) C (9) (7) (9) (6) (7) (6) C (9) (7) (9) (6) (7) (5) O (9) (6) (9) (6) (7) (5) Geometric parameters (Å, º) O1 C (18) C5 C (2) O1 H (2) C6 C (2) O2 C (16) C7 C (19) O2 C (2) C8 C (2) O3 C (17) C10 H10A O3 H (2) C10 H10B O4 C (18) C10 H10C O4 C (16) C11 C (2) O5 C (17) C11 C (2) O6 C (18) C12 C (2) O6 H (2) C12 H C1 C (2) C13 C (2) C1 C (2) C13 H C2 C (2) C14 C (2) C2 H C15 C (2) C3 C (19) C15 H C4 C (2) C16 H C4 H O7 H7A 0.95 (3) C5 C (2) O7 H7B 0.77 (3) C1 O1 H (13) O2 C9 C (13) C9 O2 C (13) O2 C9 C (13) C8 O3 H (12) C8 C9 C (13) C4 O4 C (11) O2 C10 H10A C14 O6 H (13) O2 C10 H10B O1 C1 C (13) H10A C10 H10B O1 C1 C (13) O2 C10 H10C C2 C1 C (13) H10A C10 H10C C1 C2 C (13) H10B C10 H10C C1 C2 H C16 C11 C (14) C3 C2 H C16 C11 C (13) O4 C3 C (12) C12 C11 C (15) sup-4

6 O4 C3 C (13) C13 C12 C (15) C2 C3 C (13) C13 C12 H C5 C4 O (13) C11 C12 H C5 C4 H C14 C13 C (14) O4 C4 H C14 C13 H C4 C5 C (14) C12 C13 H C4 C5 C (13) C13 C14 O (14) C6 C5 C (13) C13 C14 C (14) O5 C6 C (13) O6 C14 C (15) O5 C6 C (14) C14 C15 C (16) C7 C6 C (12) C14 C15 H C3 C7 C (13) C16 C15 H C3 C7 C (13) C11 C16 C (14) C8 C7 C (13) C11 C16 H O3 C8 C (12) C15 C16 H O3 C8 C (13) H7A O7 H7B 102 (2) C9 C8 C (13) O1 C1 C2 C (17) C10 O2 C9 C (2) C9 C1 C2 C3 0.2 (3) C10 O2 C9 C (18) C4 O4 C3 C (16) O3 C8 C9 O2 5.6 (3) C4 O4 C3 C7 2.1 (3) C7 C8 C9 O (17) C1 C2 C3 O (17) O3 C8 C9 C (17) C1 C2 C3 C7 2.2 (3) C7 C8 C9 C1 2.1 (3) C3 O4 C4 C5 4.9 (3) O1 C1 C9 O2 6.3 (3) O4 C4 C5 C6 2.7 (3) C2 C1 C9 O (17) O4 C4 C5 C (17) O1 C1 C9 C (17) C4 C5 C6 O (18) C2 C1 C9 C8 1.9 (3) C11 C5 C6 O5 3.3 (3) C4 C5 C11 C (19) C4 C5 C6 C7 2.0 (3) C6 C5 C11 C (3) C11 C5 C6 C (16) C4 C5 C11 C (3) O4 C3 C7 C (17) C6 C5 C11 C (18) C2 C3 C7 C8 2.0 (3) C16 C11 C12 C (3) O4 C3 C7 C6 2.6 (3) C5 C11 C12 C (16) C2 C3 C7 C (18) C11 C12 C13 C (3) O5 C6 C7 C (19) C12 C13 C14 O (16) C5 C6 C7 C3 4.5 (3) C12 C13 C14 C (3) O5 C6 C7 C8 4.8 (3) C13 C14 C15 C (3) C5 C6 C7 C (17) O6 C14 C15 C (16) C3 C7 C8 O (17) C12 C11 C16 C (3) C6 C7 C8 O3 0.4 (3) C5 C11 C16 C (17) C3 C7 C8 C9 0.2 (3) C14 C15 C16 C (3) C6 C7 C8 C (17) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A O7 H7B O2 i 0.77 (3) 2.57 (2) (2) 114 (2) sup-5

7 O7 H7A O6 ii 0.95 (3) 1.95 (3) (2) 167 (2) O6 H6 O1 iii 0.88 (2) 1.88 (2) (17) 167 (2) O3 H3 O (2) 1.71 (2) (16) (18) O1 H1 O7 iv 0.87 (2) 1.83 (2) (17) (19) Symmetry codes: (i) x, y, z+1; (ii) x 1, y+3/2, z 1/2; (iii) x+1, y, z+1; (iv) x, y, z 1. sup-6