Acta Cryst. (2009). E65, o736 [ doi:10.1107/S1600536809008083 ]
The title compound, C10H8O4, was isolated from the fermentation culture of the endophytic fungus Cephalosporium sp. In the crystal structure, molecules are connected into a one-dimensional chain along [101] by intermolecular O-H
O hydrogen bonds involving the hydroxyl and carbonyl functionalities. The chains are linked by non-classical C-HO interactions, forming extended two-dimensional layers approximately parallel to (11
).
A strain of fungus Cephalosporium sp. (No. 2090) was deposited in the School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou, People's Republic of China. Culture conditions: GYT medium (glucose 10 g/L, peptone 2 g/L, yeast extract 1 g/L, NaCl 2.5 g/L) and incubation at 298 K for 4 weeks. The cultures (70 L) were filtered through cheesecloth. The filtrate was concentrated to 3 L below 323 K, extracted five times by shaking with an equal volume of ethyl acetate. The extract was evaporated under reduced pressure below 323 K. The combined organic extracts were chromatographed on silica-gel, eluting with petroleum ether/ethyl acetate, to yield the title compound. Crystals were obtained by evaporation of an ethyl acetate solution.
All H atoms were positioned geometrically and treated as riding, with C—H bond lengths constrained to 0.93 (aromatic CH), 0.96 (methyl CH3), and 0.82 Å (hydroxyl OH), and with Uiso(H) = 1.5Ueq(carrier atom) or for CH3 and OH groups and Uiso(H) = 1.2Ueq(carrier C) otherwise.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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) and PLATON (Spek, 2009).
![[Figure 1]](./bh2219fig1thm.gif)
| Fig. 1. View of the title molecule with atom numbering scheme and 30% probability displacement ellipsoids for non-hydrogen atoms. |
![[Figure 2]](./bh2219fig2thm.gif)
| Fig. 2. View of the 2D layers formed by intermolecular O—H···O hydrogen bonds and weak non-conventional intermolecular C—H···O interactions. |
| C10H8O4 | F(000) = 400 |
| Mr = 192.16 | Dx = 1.500 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1738 reflections |
| a = 3.8201 (7) Å | θ = 2.6–25.5° |
| b = 15.710 (3) Å | µ = 0.12 mm−1 |
| c = 14.196 (2) Å | T = 291 K |
| β = 92.668 (2)° | Block, yellow |
| V = 851.1 (3) Å3 | 0.27 × 0.20 × 0.19 mm |
| Z = 4 |
| Bruker APEXII CCD diffractometer | 1586 independent reflections |
| Radiation source: fine-focus sealed tube | 1272 reflections with I > 2σ(I) |
| graphite | Rint = 0.021 |
| φ and ω scans | θmax = 25.5°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −4→4 |
| Tmin = 0.969, Tmax = 0.978 | k = −19→13 |
| 4781 measured reflections | l = −17→17 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
| wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0441P)2 + 0.1957P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 1586 reflections | Δρmax = 0.18 e Å−3 |
| 131 parameters | Δρmin = −0.14 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 constraints | Extinction coefficient: 0.015 (3) |
| Primary atom site location: structure-invariant direct methods |
| C10H8O4 | V = 851.1 (3) Å3 |
| Mr = 192.16 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 3.8201 (7) Å | µ = 0.12 mm−1 |
| b = 15.710 (3) Å | T = 291 K |
| c = 14.196 (2) Å | 0.27 × 0.20 × 0.19 mm |
| β = 92.668 (2)° |
| Bruker APEXII CCD diffractometer | 1586 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1272 reflections with I > 2σ(I) |
| Tmin = 0.969, Tmax = 0.978 | Rint = 0.021 |
| 4781 measured reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
| wR(F2) = 0.094 | Δρmax = 0.18 e Å−3 |
| S = 1.04 | Δρmin = −0.14 e Å−3 |
| 1586 reflections | Absolute structure: ? |
| 131 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.3482 (3) | 0.32453 (7) | 0.81217 (7) | 0.0451 (3) | |
| O2 | 0.3544 (3) | 0.19366 (7) | 0.75748 (8) | 0.0572 (4) | |
| O3 | 0.0718 (3) | 0.15766 (7) | 0.58873 (8) | 0.0552 (4) | |
| H3 | 0.1709 | 0.1476 | 0.6400 | 0.083* | |
| O4 | −0.4021 (3) | 0.39231 (7) | 0.41364 (7) | 0.0487 (3) | |
| H4 | −0.4514 | 0.3541 | 0.3759 | 0.073* | |
| C1 | 0.3853 (4) | 0.45742 (12) | 0.89102 (11) | 0.0516 (4) | |
| H1A | 0.3148 | 0.5160 | 0.8859 | 0.077* | |
| H1B | 0.6359 | 0.4542 | 0.8987 | 0.077* | |
| H1C | 0.2819 | 0.4321 | 0.9446 | 0.077* | |
| C2 | 0.2659 (4) | 0.41080 (10) | 0.80372 (10) | 0.0395 (4) | |
| C3 | 0.1028 (4) | 0.44079 (10) | 0.72629 (10) | 0.0379 (4) | |
| H3A | 0.0505 | 0.4985 | 0.7224 | 0.046* | |
| C4 | 0.0042 (3) | 0.38590 (9) | 0.64774 (9) | 0.0318 (3) | |
| C5 | −0.1641 (4) | 0.41528 (9) | 0.56587 (10) | 0.0355 (3) | |
| H5 | −0.2230 | 0.4725 | 0.5598 | 0.043* | |
| C6 | −0.2453 (4) | 0.35866 (10) | 0.49244 (10) | 0.0354 (3) | |
| C7 | −0.1659 (4) | 0.27235 (9) | 0.50066 (10) | 0.0378 (4) | |
| H7 | −0.2235 | 0.2354 | 0.4512 | 0.045* | |
| C8 | −0.0016 (4) | 0.24192 (9) | 0.58233 (10) | 0.0368 (3) | |
| C9 | 0.0880 (4) | 0.29837 (9) | 0.65755 (9) | 0.0337 (3) | |
| C10 | 0.2651 (4) | 0.26818 (10) | 0.74166 (10) | 0.0401 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0531 (7) | 0.0503 (7) | 0.0308 (5) | 0.0018 (5) | −0.0102 (5) | −0.0008 (5) |
| O2 | 0.0802 (9) | 0.0448 (7) | 0.0447 (7) | 0.0086 (6) | −0.0182 (6) | 0.0060 (5) |
| O3 | 0.0804 (9) | 0.0330 (6) | 0.0503 (7) | 0.0065 (5) | −0.0162 (6) | −0.0011 (5) |
| O4 | 0.0677 (8) | 0.0425 (6) | 0.0342 (6) | 0.0033 (5) | −0.0174 (5) | −0.0004 (5) |
| C1 | 0.0488 (10) | 0.0661 (11) | 0.0390 (9) | −0.0024 (8) | −0.0060 (7) | −0.0131 (8) |
| C2 | 0.0382 (8) | 0.0459 (9) | 0.0344 (8) | −0.0026 (7) | 0.0008 (6) | −0.0058 (6) |
| C3 | 0.0414 (8) | 0.0372 (8) | 0.0350 (8) | −0.0021 (6) | 0.0002 (6) | −0.0034 (6) |
| C4 | 0.0311 (7) | 0.0354 (8) | 0.0291 (7) | −0.0033 (6) | 0.0016 (6) | −0.0006 (6) |
| C5 | 0.0405 (8) | 0.0314 (8) | 0.0344 (7) | 0.0001 (6) | −0.0011 (6) | 0.0009 (6) |
| C6 | 0.0354 (8) | 0.0407 (8) | 0.0297 (7) | −0.0013 (6) | −0.0037 (6) | 0.0029 (6) |
| C7 | 0.0437 (8) | 0.0379 (9) | 0.0312 (7) | −0.0045 (6) | −0.0047 (6) | −0.0053 (6) |
| C8 | 0.0412 (8) | 0.0318 (8) | 0.0370 (8) | −0.0010 (6) | −0.0011 (6) | −0.0003 (6) |
| C9 | 0.0344 (8) | 0.0364 (8) | 0.0301 (7) | −0.0011 (6) | −0.0005 (6) | 0.0019 (6) |
| C10 | 0.0436 (9) | 0.0422 (9) | 0.0339 (8) | 0.0007 (7) | −0.0030 (6) | 0.0033 (6) |
| O1—C10 | 1.3626 (18) | C3—C4 | 1.4457 (19) |
| O1—C2 | 1.3951 (19) | C3—H3A | 0.9300 |
| O2—C10 | 1.2370 (18) | C4—C5 | 1.3813 (19) |
| O3—C8 | 1.3553 (18) | C4—C9 | 1.417 (2) |
| O3—H3 | 0.8200 | C5—C6 | 1.394 (2) |
| O4—C6 | 1.3518 (17) | C5—H5 | 0.9300 |
| O4—H4 | 0.8200 | C6—C7 | 1.393 (2) |
| C1—C2 | 1.493 (2) | C7—C8 | 1.378 (2) |
| C1—H1A | 0.9600 | C7—H7 | 0.9300 |
| C1—H1B | 0.9600 | C8—C9 | 1.418 (2) |
| C1—H1C | 0.9600 | C9—C10 | 1.426 (2) |
| C2—C3 | 1.325 (2) | ||
| C10—O1—C2 | 121.61 (11) | C4—C5—C6 | 119.64 (13) |
| C8—O3—H3 | 109.5 | C4—C5—H5 | 120.2 |
| C6—O4—H4 | 109.5 | C6—C5—H5 | 120.2 |
| C2—C1—H1A | 109.5 | O4—C6—C7 | 122.43 (13) |
| C2—C1—H1B | 109.5 | O4—C6—C5 | 116.35 (13) |
| H1A—C1—H1B | 109.5 | C7—C6—C5 | 121.22 (13) |
| C2—C1—H1C | 109.5 | C8—C7—C6 | 119.81 (13) |
| H1A—C1—H1C | 109.5 | C8—C7—H7 | 120.1 |
| H1B—C1—H1C | 109.5 | C6—C7—H7 | 120.1 |
| C3—C2—O1 | 120.81 (13) | O3—C8—C7 | 118.69 (13) |
| C3—C2—C1 | 128.92 (15) | O3—C8—C9 | 121.23 (13) |
| O1—C2—C1 | 110.27 (13) | C7—C8—C9 | 120.08 (13) |
| C2—C3—C4 | 121.57 (14) | C4—C9—C8 | 119.18 (12) |
| C2—C3—H3A | 119.2 | C4—C9—C10 | 120.08 (13) |
| C4—C3—H3A | 119.2 | C8—C9—C10 | 120.74 (13) |
| C5—C4—C9 | 120.07 (12) | O2—C10—O1 | 115.39 (13) |
| C5—C4—C3 | 122.96 (13) | O2—C10—C9 | 125.66 (14) |
| C9—C4—C3 | 116.96 (12) | O1—C10—C9 | 118.96 (13) |
| C10—O1—C2—C3 | 0.1 (2) | C5—C4—C9—C8 | 0.3 (2) |
| C10—O1—C2—C1 | 179.78 (13) | C3—C4—C9—C8 | −179.69 (13) |
| O1—C2—C3—C4 | −0.1 (2) | C5—C4—C9—C10 | 179.32 (13) |
| C1—C2—C3—C4 | −179.74 (14) | C3—C4—C9—C10 | −0.66 (19) |
| C2—C3—C4—C5 | −179.60 (14) | O3—C8—C9—C4 | −179.69 (13) |
| C2—C3—C4—C9 | 0.4 (2) | C7—C8—C9—C4 | 0.5 (2) |
| C9—C4—C5—C6 | −1.1 (2) | O3—C8—C9—C10 | 1.3 (2) |
| C3—C4—C5—C6 | 178.85 (13) | C7—C8—C9—C10 | −178.57 (13) |
| C4—C5—C6—O4 | −178.42 (12) | C2—O1—C10—O2 | 179.49 (13) |
| C4—C5—C6—C7 | 1.3 (2) | C2—O1—C10—C9 | −0.4 (2) |
| O4—C6—C7—C8 | 179.14 (14) | C4—C9—C10—O2 | −179.17 (15) |
| C5—C6—C7—C8 | −0.5 (2) | C8—C9—C10—O2 | −0.2 (2) |
| C6—C7—C8—O3 | 179.79 (14) | C4—C9—C10—O1 | 0.7 (2) |
| C6—C7—C8—C9 | −0.3 (2) | C8—C9—C10—O1 | 179.67 (13) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O2 | 0.82 | 1.92 | 2.6426 (16) | 146 |
| O4—H4···O2i | 0.82 | 1.96 | 2.7225 (15) | 155 |
| C5—H5···O4ii | 0.93 | 2.60 | 3.4659 (19) | 155 |
| Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x−1, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O4—H4···O2i | 0.82 | 1.96 | 2.7225 (15) | 155 |
| C5—H5···O4ii | 0.93 | 2.60 | 3.4659 (19) | 155 |
| Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x−1, −y+1, −z+1. |
The authors acknowledge financial support from the National Natural Science Foundation of China (No. 40776073), the Basic Research Program of Science and Technology, Ministry of Science and Technology of China (No. 2007FY210500) and the Youthful Fund of Guangdong Medical College (No. XQ0511).
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Endophytic fungi have proven to be a rich source of novel structural compounds with interesting biological activities and a high level of biodiversity. In the course of our search for new or bioactive secondary metabolites from the marine fungi (Shao et al., 2007). we have investigated an endophytic strain Cephalosporium sp. (Wei et al., 2008). The title compound was previously isolated from the organic extracts of the fungus Ceratocystis minor (Hemingway et al., 1977), and elucidated on the basic of spectroscopic analysis (Kendall et al., 1989). Herein, the title compound was isolated from the fermentation culture of the endophytic fungus Cephalosporium sp., and its crystal structure is reported.
The asymmetric unit of the title compound contains one independent molecule (Fig. 1), in which the bond lengths and angles are within the expected ranges. The structural analysis reveals that the most relevant feature is the arrangement of the molecules, which are connected to form a one-dimensional chain along the [101] direction, by the formation of intermolecular O—H···O hydrogen bonds. Furthermore, weak non-conventional intermolecular C—H···O interactions are observed (Nangia, 2002), in which C5—H5 is a donor and O4 is an acceptor. These interactions consolidate the crystal packing. Details of hydrogen bonds are given in Table 1.