Acta Cryst. (2010). E66, o634 [ doi:10.1107/S1600536810005040 ]
The title compound, C10H11NO4, was extracted from a culture broth of Penicillium verruculosum YL-52. The molecular structure is essentially planar, with an r.m.s. deviation of 0.01342 (2) Å for the non-H atoms. In the crystal structure, adjacent molecules are connected into a centrosymmetric dimer through a pair of O-H
O hydrogen bonds. The dimers are further extended into a chain by weak C-HO hydrogen bonds.
The roots of Stellera Chamaejasme L was collected in Qinling mountain of Taibai town in Shaanxi province, P. R. China, in August, 2007, and the fungal strain was isolated from the rhizosphere of the plant above, and deposited in our laboratory of natural product research, Northwest A&F University, Shaanxi Province, the People's Republic of China (culture collection number YL-52), and identified as Penicillium verruculosum YL-52. Repeated column chromatography of ethyl acetate extract of the culture broth of Penicillium verruculosum YL-52 provided the title compound.
All H atoms were positioned geometrically and treated as riding, with C—H bond lengths constrained to 0.93 Å (CH), 0.97 Å (CH2) and 0.96 Å (CH3), and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
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) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
![[Figure 1]](./is2521fig1thm.gif)
| Fig. 1. View of the title molecular structure with atom numbering scheme and 30% probability displacement ellipsoids for non-hydrogen atoms. |
![[Figure 2]](./is2521fig2thm.gif)
| Fig. 2. View of the two-dimensional sheet (O—H···O and C—H···O hydrogen bonds are indicated as broken lines). |
| C10H11NO4 | Z = 2 |
| Mr = 209.20 | F(000) = 220 |
| Triclinic, P1 | Dx = 1.385 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 6.5384 (14) Å | Cell parameters from 773 reflections |
| b = 7.5309 (17) Å | θ = 0.00–0.00° |
| c = 10.405 (2) Å | µ = 0.11 mm−1 |
| α = 93.009 (3)° | T = 296 K |
| β = 101.247 (2)° | Block, colourless |
| γ = 90.410 (3)° | 0.33 × 0.12 × 0.08 mm |
| V = 501.74 (19) Å3 |
| Bruker APEXII CCD diffractometer | 1849 independent reflections |
| Radiation source: fine-focus sealed tube | 1255 reflections with I > 2σ(I) |
| graphite | Rint = 0.024 |
| φ and ω scans | θmax = 25.5°, θmin = 2.7° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
| Tmin = 0.965, Tmax = 0.991 | k = −9→9 |
| 3845 measured reflections | l = −12→12 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.125 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0581P)2 + 0.0541P] where P = (Fo2 + 2Fc2)/3 |
| 1849 reflections | (Δ/σ)max < 0.001 |
| 139 parameters | Δρmax = 0.17 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| C10H11NO4 | γ = 90.410 (3)° |
| Mr = 209.20 | V = 501.74 (19) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 6.5384 (14) Å | Mo Kα radiation |
| b = 7.5309 (17) Å | µ = 0.11 mm−1 |
| c = 10.405 (2) Å | T = 296 K |
| α = 93.009 (3)° | 0.33 × 0.12 × 0.08 mm |
| β = 101.247 (2)° |
| Bruker APEXII CCD diffractometer | 1849 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1255 reflections with I > 2σ(I) |
| Tmin = 0.965, Tmax = 0.991 | Rint = 0.024 |
| 3845 measured reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
| wR(F2) = 0.125 | Δρmax = 0.17 e Å−3 |
| S = 1.05 | Δρmin = −0.19 e Å−3 |
| 1849 reflections | Absolute structure: ? |
| 139 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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. |
| x | y | z | Uiso*/Ueq | ||
| O2 | 1.2795 (3) | 0.5891 (2) | 0.92347 (15) | 0.0617 (5) | |
| O1 | 1.5542 (3) | 0.5091 (3) | 0.83867 (17) | 0.0664 (5) | |
| H1 | 1.5982 | 0.4818 | 0.9142 | 0.100* | |
| N1 | 0.9689 (2) | 0.7432 (2) | 0.55825 (16) | 0.0375 (4) | |
| O4 | 0.6865 (2) | 0.8327 (2) | 0.64451 (17) | 0.0611 (5) | |
| O3 | 1.2017 (2) | 0.6881 (2) | 0.42194 (15) | 0.0555 (5) | |
| C4 | 1.0334 (3) | 0.7417 (3) | 0.4361 (2) | 0.0372 (5) | |
| C3 | 1.0819 (3) | 0.6860 (3) | 0.6763 (2) | 0.0403 (5) | |
| H3 | 1.0143 | 0.6904 | 0.7472 | 0.048* | |
| C5 | 0.8620 (3) | 0.8155 (3) | 0.3422 (2) | 0.0382 (5) | |
| C8 | 0.8650 (3) | 0.8428 (3) | 0.2160 (2) | 0.0445 (6) | |
| C2 | 1.2744 (3) | 0.6264 (3) | 0.6983 (2) | 0.0437 (6) | |
| H2 | 1.3491 | 0.6184 | 0.6309 | 0.052* | |
| C1 | 1.3693 (3) | 0.5730 (3) | 0.8297 (2) | 0.0441 (6) | |
| C6 | 0.6859 (3) | 0.8529 (3) | 0.4118 (2) | 0.0458 (6) | |
| H6A | 0.6463 | 0.9765 | 0.4060 | 0.055* | |
| H6B | 0.5654 | 0.7782 | 0.3743 | 0.055* | |
| C7 | 0.7675 (3) | 0.8117 (3) | 0.5505 (2) | 0.0433 (5) | |
| C10 | 0.6796 (4) | 0.9171 (3) | 0.1284 (2) | 0.0580 (7) | |
| H10A | 0.5714 | 0.9396 | 0.1773 | 0.087* | |
| H10B | 0.6294 | 0.8331 | 0.0563 | 0.087* | |
| H10C | 0.7192 | 1.0262 | 0.0953 | 0.087* | |
| C9 | 1.0460 (4) | 0.8041 (4) | 0.1519 (3) | 0.0675 (8) | |
| H9A | 1.1076 | 0.9138 | 0.1338 | 0.101* | |
| H9B | 0.9992 | 0.7347 | 0.0713 | 0.101* | |
| H9C | 1.1476 | 0.7388 | 0.2093 | 0.101* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O2 | 0.0608 (11) | 0.0854 (13) | 0.0385 (10) | 0.0281 (9) | 0.0066 (8) | 0.0098 (8) |
| O1 | 0.0544 (11) | 0.0958 (14) | 0.0481 (10) | 0.0294 (10) | 0.0024 (8) | 0.0214 (10) |
| N1 | 0.0320 (9) | 0.0440 (10) | 0.0355 (10) | 0.0051 (8) | 0.0029 (8) | 0.0055 (8) |
| O4 | 0.0491 (10) | 0.0836 (12) | 0.0550 (11) | 0.0187 (9) | 0.0177 (9) | 0.0121 (9) |
| O3 | 0.0375 (9) | 0.0838 (12) | 0.0452 (9) | 0.0178 (8) | 0.0060 (7) | 0.0105 (8) |
| C4 | 0.0296 (11) | 0.0413 (12) | 0.0396 (12) | 0.0026 (9) | 0.0032 (9) | 0.0046 (9) |
| C3 | 0.0427 (13) | 0.0417 (12) | 0.0348 (12) | 0.0027 (10) | 0.0024 (10) | 0.0065 (9) |
| C5 | 0.0328 (11) | 0.0386 (12) | 0.0413 (13) | 0.0022 (9) | 0.0014 (9) | 0.0054 (9) |
| C8 | 0.0448 (13) | 0.0447 (13) | 0.0414 (13) | 0.0022 (10) | 0.0009 (10) | 0.0051 (10) |
| C2 | 0.0446 (14) | 0.0478 (13) | 0.0373 (12) | 0.0043 (11) | 0.0027 (10) | 0.0072 (10) |
| C1 | 0.0426 (13) | 0.0442 (13) | 0.0425 (13) | 0.0081 (10) | 0.0005 (11) | 0.0045 (10) |
| C6 | 0.0360 (12) | 0.0521 (13) | 0.0480 (14) | 0.0092 (10) | 0.0033 (10) | 0.0093 (11) |
| C7 | 0.0364 (12) | 0.0478 (13) | 0.0465 (14) | 0.0048 (10) | 0.0094 (11) | 0.0055 (10) |
| C10 | 0.0571 (16) | 0.0625 (16) | 0.0484 (15) | 0.0082 (12) | −0.0073 (12) | 0.0138 (12) |
| C9 | 0.0633 (17) | 0.093 (2) | 0.0487 (15) | 0.0124 (15) | 0.0150 (13) | 0.0130 (14) |
| O2—C1 | 1.234 (3) | C8—C9 | 1.491 (3) |
| O1—C1 | 1.293 (3) | C8—C10 | 1.499 (3) |
| O1—H1 | 0.8200 | C2—C1 | 1.465 (3) |
| N1—C3 | 1.395 (3) | C2—H2 | 0.9300 |
| N1—C7 | 1.407 (3) | C6—C7 | 1.488 (3) |
| N1—C4 | 1.415 (3) | C6—H6A | 0.9700 |
| O4—C7 | 1.203 (3) | C6—H6B | 0.9700 |
| O3—C4 | 1.207 (2) | C10—H10A | 0.9600 |
| C4—C5 | 1.469 (3) | C10—H10B | 0.9600 |
| C3—C2 | 1.321 (3) | C10—H10C | 0.9600 |
| C3—H3 | 0.9300 | C9—H9A | 0.9600 |
| C5—C8 | 1.343 (3) | C9—H9B | 0.9600 |
| C5—C6 | 1.496 (3) | C9—H9C | 0.9600 |
| C1—O1—H1 | 109.5 | C7—C6—C5 | 105.09 (17) |
| C3—N1—C7 | 120.90 (18) | C7—C6—H6A | 110.7 |
| C3—N1—C4 | 127.07 (17) | C5—C6—H6A | 110.7 |
| C7—N1—C4 | 112.03 (17) | C7—C6—H6B | 110.7 |
| O3—C4—N1 | 122.39 (18) | C5—C6—H6B | 110.7 |
| O3—C4—C5 | 130.8 (2) | H6A—C6—H6B | 108.8 |
| N1—C4—C5 | 106.80 (17) | O4—C7—N1 | 122.9 (2) |
| C2—C3—N1 | 127.1 (2) | O4—C7—C6 | 129.1 (2) |
| C2—C3—H3 | 116.5 | N1—C7—C6 | 107.93 (18) |
| N1—C3—H3 | 116.5 | C8—C10—H10A | 109.5 |
| C8—C5—C4 | 125.4 (2) | C8—C10—H10B | 109.5 |
| C8—C5—C6 | 126.63 (19) | H10A—C10—H10B | 109.5 |
| C4—C5—C6 | 107.97 (18) | C8—C10—H10C | 109.5 |
| C5—C8—C9 | 124.3 (2) | H10A—C10—H10C | 109.5 |
| C5—C8—C10 | 120.9 (2) | H10B—C10—H10C | 109.5 |
| C9—C8—C10 | 114.8 (2) | C8—C9—H9A | 109.5 |
| C3—C2—C1 | 119.5 (2) | C8—C9—H9B | 109.5 |
| C3—C2—H2 | 120.2 | H9A—C9—H9B | 109.5 |
| C1—C2—H2 | 120.2 | C8—C9—H9C | 109.5 |
| O2—C1—O1 | 123.3 (2) | H9A—C9—H9C | 109.5 |
| O2—C1—C2 | 122.4 (2) | H9B—C9—H9C | 109.5 |
| O1—C1—C2 | 114.3 (2) | ||
| C3—N1—C4—O3 | −0.1 (3) | C6—C5—C8—C10 | −0.4 (3) |
| C7—N1—C4—O3 | 179.89 (19) | N1—C3—C2—C1 | 179.57 (19) |
| C3—N1—C4—C5 | −179.71 (17) | C3—C2—C1—O2 | −3.5 (3) |
| C7—N1—C4—C5 | 0.3 (2) | C3—C2—C1—O1 | 177.0 (2) |
| C7—N1—C3—C2 | −176.9 (2) | C8—C5—C6—C7 | −176.1 (2) |
| C4—N1—C3—C2 | 3.1 (3) | C4—C5—C6—C7 | 4.3 (2) |
| O3—C4—C5—C8 | −2.1 (4) | C3—N1—C7—O4 | 3.7 (3) |
| N1—C4—C5—C8 | 177.4 (2) | C4—N1—C7—O4 | −176.4 (2) |
| O3—C4—C5—C6 | 177.6 (2) | C3—N1—C7—C6 | −177.54 (18) |
| N1—C4—C5—C6 | −2.9 (2) | C4—N1—C7—C6 | 2.4 (2) |
| C4—C5—C8—C9 | −0.8 (4) | C5—C6—C7—O4 | 174.6 (2) |
| C6—C5—C8—C9 | 179.6 (2) | C5—C6—C7—N1 | −4.1 (2) |
| C4—C5—C8—C10 | 179.3 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2i | 0.82 | 1.83 | 2.647 (2) | 174 |
| C6—H6A···O4ii | 0.97 | 2.60 | 3.399 (3) | 140 |
| Symmetry codes: (i) −x+3, −y+1, −z+2; (ii) −x+1, −y+2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2i | 0.82 | 1.83 | 2.647 (2) | 174 |
| C6—H6A···O4ii | 0.97 | 2.60 | 3.399 (3) | 140 |
| Symmetry codes: (i) −x+3, −y+1, −z+2; (ii) −x+1, −y+2, −z+1. |
This work was supported the National Natural Science Foundation of China (grant Nos. 30571402 and 30771454).
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Stellera chamaejasme L belongs to a toxic plant and its root has been used as Chinese traditional herb medicine in China. Our previous study resulted in isolating a fungal strain from the rhizosphere of Stellera Chamaejasme L identified as Penicillium verruculosum YL-52 (Yang et al., 2009). In this controbution, we reported the crystal structure of the title compound which was obtained from the culture broth of Penicillium verruculosum YL-52.
The bond lengths and angles of the title compound are within normal ranges (Cheng et al., 2009). In the crystal structure, the molecule, excluding methyl H atoms, is essentially planar, with an r.m.s. deviation of 0.01342 (2) Å. Moreover, adjacent two molecules are connected into a dimer through two head to head O1—H1···O2 hydrogen bonds. The dimers are further extended into a one-dimensional chain by weak C—H···O hydrogen bonds along the b axis, in which C6—H6A is donor and O4 is acceptor (Table 1 and Fig. 2).