Literature DB >> 21588390

Trichodermin (12,13-ep-oxy-trichethec-9-en-4β-yl 4-fluoro-benzoate).

Xu-Hui Xu, Zong-Cheng Wang, Jing-Li Cheng, Yong Zhou, Jin-Hao Zhao.   

Abstract

IN THE TITLE TRICHODERMIN COMPOUND (SYSTEMATIC NAME: 12,13-ep-oxy-trichothec-9-en-4β-yl 4-fluoro-benzoate), C(22)H(25)FO(4), the five-membered ring displays an envelope conformation, whereas the two six-membered rings show the different conformations, viz. chair and half-chair. As for the seven-membered ring, the dihedral angle between the mean planes formed by the four C atoms of the envelope unit and the three C and one O atoms of the six-membered chair is 68.67 (2)°; these two mean planes are nearly perpendicular to the ep-oxy ring with angles of 87.97 (2)and 88.14 (2)°, respectively.

Entities:  

Year:  2010        PMID： 21588390      PMCID： PMC3007378          DOI： 10.1107/S1600536810028461

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

The endophytic fungi Trichoderma taxi sp. nov. can produce a compound with fungicidal activity, Trichodermin (Zhang et al., 2007 ▶), which is a member of the 4β-acet­oxy-12,13-ep­oxy­trichothecene family (Nielsen et al., 2005 ▶). For a related Trichodermin structure, see: Chen et al. (2008 ▶). For the structures of Trichodermin derivatives, see: Cheng et al. (2009 ▶); Zhao et al. (2010 ▶). For the extinction correction, see: Larson (1970 ▶).

Experimental

Crystal data

C22H25FO4 M = 372.42 Orthorhombic, a = 8.1643 (4) Å b = 9.9979 (4) Å c = 23.6503 (9) Å V = 1930.48 (14) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 296 K 0.49 × 0.38 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.956, T max = 0.974 16756 measured reflections 2183 independent reflections 1760 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.086 S = 1.00 2183 reflections 248 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.16 e Å−3 Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028461/si2275sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028461/si2275Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H25FO4F(000) = 792
Mr = 372.42Dx = 1.281 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 13225 reflections
a = 8.1643 (4) Åθ = 3.0–27.4°
b = 9.9979 (4) ŵ = 0.09 mm−1
c = 23.6503 (9) ÅT = 296 K
V = 1930.48 (14) Å3Chunk, colorless
Z = 40.49 × 0.38 × 0.28 mm
Rigaku R-AXIS RAPID/ZJUG diffractometer2183 independent reflections
Radiation source: rolling anode1760 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 10.00 pixels mm-1θmax = 26.0°, θmin = 3.0°
ω scansh = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −11→12
Tmin = 0.956, Tmax = 0.974l = −29→29
16756 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.086w = 1/[σ2(Fo2) + (0.0289P)2 + 0.6417P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2183 reflectionsΔρmax = 0.16 e Å−3
248 parametersΔρmin = −0.15 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0158 (10)
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.
xyzUiso*/Ueq
O30.5928 (2)0.17729 (19)0.38572 (8)0.0590 (5)
O10.3925 (2)0.58802 (17)0.41271 (7)0.0552 (5)
C90.3220 (3)0.4541 (3)0.32881 (10)0.0448 (6)
C100.3644 (3)0.3262 (2)0.36490 (10)0.0452 (6)
C40.4116 (3)0.5769 (2)0.35259 (9)0.0467 (6)
H40.52860.56830.34400.056*
O40.8524 (3)0.2138 (2)0.35947 (10)0.0769 (7)
C170.7821 (3)0.0043 (3)0.40042 (10)0.0481 (6)
C60.2105 (4)0.7223 (3)0.30230 (11)0.0516 (7)
C80.1381 (3)0.4869 (3)0.33098 (11)0.0529 (7)
H8A0.07630.41000.31790.063*
H8B0.10660.50440.36980.063*
C50.3514 (4)0.7072 (3)0.32885 (11)0.0514 (7)
H50.41770.78210.33310.062*
C180.6592 (4)−0.0777 (3)0.42095 (12)0.0576 (7)
H180.5513−0.04800.42100.069*
O20.2982 (3)0.2494 (2)0.46425 (8)0.0710 (6)
C70.0950 (4)0.6076 (3)0.29473 (12)0.0607 (7)
H7A0.09520.58100.25530.073*
H7B−0.01490.63690.30410.073*
C160.7495 (3)0.1413 (3)0.37958 (11)0.0521 (7)
C220.9427 (4)−0.0412 (3)0.40068 (11)0.0565 (7)
H221.02570.01370.38690.068*
F10.8929 (3)−0.36743 (17)0.46149 (10)0.1008 (7)
C200.8560 (4)−0.2447 (3)0.44071 (14)0.0665 (8)
C20.5964 (4)0.4062 (3)0.42280 (13)0.0663 (9)
H2A0.67250.47580.41170.080*
H2B0.64510.35410.45300.080*
C130.1585 (4)0.8535 (3)0.27722 (11)0.0645 (8)
H13A0.23450.92200.28820.097*
H13B0.05110.87620.29070.097*
H13C0.15640.84630.23670.097*
C110.3138 (3)0.3591 (3)0.42485 (11)0.0518 (7)
C150.2899 (4)0.1980 (3)0.34125 (13)0.0591 (7)
H15A0.29960.12770.36870.089*
H15B0.34690.17280.30740.089*
H15C0.17640.21260.33270.089*
C140.3756 (4)0.4322 (3)0.26721 (11)0.0636 (8)
H14A0.37110.51560.24720.095*
H14B0.30350.36900.24950.095*
H14C0.48550.39830.26650.095*
C10.5533 (3)0.3168 (3)0.37240 (12)0.0549 (7)
H10.61030.34630.33810.066*
C30.4327 (4)0.4666 (3)0.44166 (11)0.0614 (8)
H30.43120.48020.48270.074*
C120.1571 (4)0.3327 (3)0.45174 (12)0.0694 (8)
H12A0.12040.39450.48070.083*
H12B0.07060.29460.42870.083*
C190.6964 (4)−0.2039 (3)0.44136 (14)0.0680 (9)
H190.6145−0.25960.45520.082*
C210.9811 (4)−0.1672 (3)0.42114 (13)0.0651 (8)
H211.0887−0.19790.42150.078*
U11U22U33U12U13U23
O30.0414 (10)0.0521 (10)0.0836 (13)−0.0025 (9)0.0026 (10)0.0180 (10)
O10.0717 (13)0.0486 (9)0.0453 (9)−0.0096 (10)−0.0136 (9)0.0011 (8)
C90.0439 (15)0.0497 (14)0.0408 (12)−0.0047 (12)−0.0050 (11)0.0007 (11)
C100.0418 (14)0.0432 (13)0.0505 (13)−0.0070 (12)−0.0056 (11)0.0035 (11)
C40.0462 (15)0.0498 (13)0.0441 (12)−0.0082 (13)−0.0059 (11)0.0058 (11)
O40.0477 (12)0.0872 (16)0.0958 (15)−0.0058 (12)0.0064 (11)0.0384 (13)
C170.0456 (15)0.0544 (15)0.0443 (12)−0.0032 (13)−0.0004 (11)−0.0004 (12)
C60.0571 (17)0.0521 (16)0.0457 (13)0.0041 (14)−0.0044 (13)0.0033 (12)
C80.0462 (15)0.0538 (15)0.0587 (15)−0.0060 (13)−0.0093 (13)−0.0004 (13)
C50.0588 (17)0.0450 (14)0.0505 (13)−0.0086 (13)−0.0078 (13)0.0083 (11)
C180.0453 (16)0.0545 (16)0.0729 (17)−0.0071 (14)−0.0045 (14)0.0025 (14)
O20.0814 (15)0.0665 (12)0.0651 (12)−0.0101 (12)0.0039 (11)0.0243 (11)
C70.0522 (17)0.0653 (17)0.0647 (16)0.0015 (15)−0.0151 (14)0.0030 (14)
C160.0431 (15)0.0613 (16)0.0518 (14)−0.0041 (13)−0.0025 (12)0.0086 (13)
C220.0476 (16)0.0649 (18)0.0568 (15)−0.0010 (14)0.0076 (13)0.0007 (14)
F10.0951 (15)0.0492 (9)0.1582 (19)0.0028 (11)−0.0263 (15)0.0116 (11)
C200.068 (2)0.0427 (14)0.089 (2)0.0002 (15)−0.0128 (17)−0.0025 (15)
C20.066 (2)0.0576 (16)0.0751 (18)−0.0158 (16)−0.0304 (16)0.0173 (15)
C130.075 (2)0.0609 (17)0.0571 (15)0.0136 (17)−0.0039 (15)0.0045 (14)
C110.0595 (17)0.0507 (15)0.0453 (13)−0.0089 (14)−0.0027 (12)0.0101 (12)
C150.0565 (17)0.0485 (15)0.0723 (18)−0.0081 (14)−0.0036 (15)−0.0055 (14)
C140.0688 (19)0.0741 (19)0.0481 (14)0.0076 (18)−0.0015 (14)−0.0008 (14)
C10.0460 (15)0.0491 (14)0.0697 (16)−0.0067 (13)−0.0063 (14)0.0159 (14)
C30.085 (2)0.0547 (15)0.0449 (13)−0.0137 (17)−0.0199 (15)0.0086 (12)
C120.072 (2)0.073 (2)0.0625 (17)−0.0079 (19)0.0111 (16)0.0079 (16)
C190.062 (2)0.0494 (16)0.093 (2)−0.0131 (15)−0.0047 (17)0.0045 (15)
C210.0585 (18)0.0628 (18)0.0739 (18)0.0097 (16)0.0012 (15)−0.0068 (16)
O3—C161.337 (3)C7—H7A0.9700
O3—C11.466 (3)C7—H7B0.9700
O1—C31.432 (3)C22—C211.386 (4)
O1—C41.435 (3)C22—H220.9300
C9—C141.537 (4)F1—C201.356 (3)
C9—C41.536 (3)C20—C211.364 (4)
C9—C81.537 (4)C20—C191.365 (5)
C9—C101.576 (3)C2—C11.531 (4)
C10—C111.513 (4)C2—C31.533 (5)
C10—C151.525 (3)C2—H2A0.9700
C10—C11.555 (4)C2—H2B0.9700
C4—C51.501 (3)C13—H13A0.9600
C4—H40.9800C13—H13B0.9600
O4—C161.207 (3)C13—H13C0.9600
C17—C181.384 (4)C11—C121.452 (4)
C17—C221.388 (4)C11—C31.502 (4)
C17—C161.480 (4)C15—H15A0.9600
C6—C51.319 (4)C15—H15B0.9600
C6—C71.496 (4)C15—H15C0.9600
C6—C131.501 (4)C14—H14A0.9600
C8—C71.522 (4)C14—H14B0.9600
C8—H8A0.9700C14—H14C0.9600
C8—H8B0.9700C1—H10.9800
C5—H50.9300C3—H30.9800
C18—C191.384 (4)C12—H12A0.9700
C18—H180.9300C12—H12B0.9700
O2—C111.445 (3)C19—H190.9300
O2—C121.452 (4)C21—H210.9300
C16—O3—C1116.3 (2)C1—C2—C3104.8 (2)
C3—O1—C4112.6 (2)C1—C2—H2A110.8
C14—C9—C4109.0 (2)C3—C2—H2A110.8
C14—C9—C8109.9 (2)C1—C2—H2B110.8
C4—C9—C8106.4 (2)C3—C2—H2B110.8
C14—C9—C10109.6 (2)H2A—C2—H2B108.9
C4—C9—C10110.21 (18)C6—C13—H13A109.5
C8—C9—C10111.7 (2)C6—C13—H13B109.5
C11—C10—C15114.7 (2)H13A—C13—H13B109.5
C11—C10—C1100.2 (2)C6—C13—H13C109.5
C15—C10—C1112.7 (2)H13A—C13—H13C109.5
C11—C10—C9105.7 (2)H13B—C13—H13C109.5
C15—C10—C9113.3 (2)O2—C11—C1260.15 (17)
C1—C10—C9109.2 (2)O2—C11—C3115.4 (2)
O1—C4—C5105.6 (2)C12—C11—C3125.7 (3)
O1—C4—C9111.87 (19)O2—C11—C10117.6 (2)
C5—C4—C9113.6 (2)C12—C11—C10127.7 (2)
O1—C4—H4108.6C3—C11—C10103.1 (2)
C5—C4—H4108.6C10—C15—H15A109.5
C9—C4—H4108.6C10—C15—H15B109.5
C18—C17—C22119.3 (3)H15A—C15—H15B109.5
C18—C17—C16122.4 (3)C10—C15—H15C109.5
C22—C17—C16118.3 (2)H15A—C15—H15C109.5
C5—C6—C7121.2 (2)H15B—C15—H15C109.5
C5—C6—C13122.4 (3)C9—C14—H14A109.5
C7—C6—C13116.4 (2)C9—C14—H14B109.5
C7—C8—C9112.1 (2)H14A—C14—H14B109.5
C7—C8—H8A109.2C9—C14—H14C109.5
C9—C8—H8A109.2H14A—C14—H14C109.5
C7—C8—H8B109.2H14B—C14—H14C109.5
C9—C8—H8B109.2O3—C1—C2109.7 (2)
H8A—C8—H8B107.9O3—C1—C10107.5 (2)
C6—C5—C4124.3 (2)C2—C1—C10106.4 (2)
C6—C5—H5117.9O3—C1—H1111.0
C4—C5—H5117.9C2—C1—H1111.0
C19—C18—C17120.2 (3)C10—C1—H1111.0
C19—C18—H18119.9O1—C3—C11109.4 (2)
C17—C18—H18119.9O1—C3—C2113.3 (2)
C11—O2—C1260.18 (17)C11—C3—C2101.8 (2)
C6—C7—C8113.3 (2)O1—C3—H3110.7
C6—C7—H7A108.9C11—C3—H3110.7
C8—C7—H7A108.9C2—C3—H3110.7
C6—C7—H7B108.9O2—C12—C1159.67 (18)
C8—C7—H7B108.9O2—C12—H12A117.8
H7A—C7—H7B107.7C11—C12—H12A117.8
O4—C16—O3123.2 (3)O2—C12—H12B117.8
O4—C16—C17124.2 (3)C11—C12—H12B117.8
O3—C16—C17112.6 (2)H12A—C12—H12B114.9
C21—C22—C17120.9 (3)C20—C19—C18118.5 (3)
C21—C22—H22119.6C20—C19—H19120.7
C17—C22—H22119.6C18—C19—H19120.7
F1—C20—C21118.1 (3)C20—C21—C22117.8 (3)
F1—C20—C19118.6 (3)C20—C21—H21121.1
C21—C20—C19123.3 (3)C22—C21—H21121.1
C14—C9—C10—C11177.8 (2)C12—O2—C11—C10−119.7 (3)
C4—C9—C10—C1157.9 (3)C15—C10—C11—O238.5 (3)
C8—C9—C10—C11−60.2 (3)C1—C10—C11—O2−82.5 (3)
C14—C9—C10—C15−55.8 (3)C9—C10—C11—O2164.1 (2)
C4—C9—C10—C15−175.7 (2)C15—C10—C11—C12−33.7 (4)
C8—C9—C10—C1566.2 (3)C1—C10—C11—C12−154.7 (3)
C14—C9—C10—C170.8 (3)C9—C10—C11—C1291.9 (3)
C4—C9—C10—C1−49.2 (3)C15—C10—C11—C3166.8 (2)
C8—C9—C10—C1−167.2 (2)C1—C10—C11—C345.8 (2)
C3—O1—C4—C5175.3 (2)C9—C10—C11—C3−67.6 (2)
C3—O1—C4—C951.3 (3)C16—O3—C1—C2−81.3 (3)
C14—C9—C4—O1−168.6 (2)C16—O3—C1—C10163.5 (2)
C8—C9—C4—O172.9 (3)C3—C2—C1—O3−117.3 (2)
C10—C9—C4—O1−48.3 (3)C3—C2—C1—C10−1.4 (3)
C14—C9—C4—C572.0 (3)C11—C10—C1—O390.8 (2)
C8—C9—C4—C5−46.5 (3)C15—C10—C1—O3−31.6 (3)
C10—C9—C4—C5−167.7 (2)C9—C10—C1—O3−158.49 (19)
C14—C9—C8—C7−56.3 (3)C11—C10—C1—C2−26.7 (3)
C4—C9—C8—C761.5 (3)C15—C10—C1—C2−149.1 (2)
C10—C9—C8—C7−178.2 (2)C9—C10—C1—C284.0 (2)
C7—C6—C5—C41.4 (4)C4—O1—C3—C11−64.5 (3)
C13—C6—C5—C4−177.5 (3)C4—O1—C3—C248.2 (3)
O1—C4—C5—C6−105.8 (3)O2—C11—C3—O1−157.9 (2)
C9—C4—C5—C617.1 (4)C12—C11—C3—O1−87.6 (3)
C22—C17—C18—C19−0.2 (4)C10—C11—C3—O172.5 (3)
C16—C17—C18—C19−178.3 (3)O2—C11—C3—C282.0 (3)
C5—C6—C7—C812.8 (4)C12—C11—C3—C2152.3 (3)
C13—C6—C7—C8−168.2 (2)C10—C11—C3—C2−47.6 (2)
C9—C8—C7—C6−45.5 (3)C1—C2—C3—O1−88.0 (2)
C1—O3—C16—O4−6.6 (4)C1—C2—C3—C1129.3 (3)
C1—O3—C16—C17173.1 (2)C3—C11—C12—O2−101.4 (3)
C18—C17—C16—O4−177.1 (3)C10—C11—C12—O2103.4 (3)
C22—C17—C16—O44.7 (4)F1—C20—C19—C18179.0 (3)
C18—C17—C16—O33.3 (4)C21—C20—C19—C180.3 (5)
C22—C17—C16—O3−174.9 (2)C17—C18—C19—C200.0 (5)
C18—C17—C22—C210.0 (4)F1—C20—C21—C22−179.1 (3)
C16—C17—C22—C21178.2 (2)C19—C20—C21—C22−0.4 (5)
C12—O2—C11—C3118.1 (3)C17—C22—C21—C200.3 (4)
  7 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Trichothecene production by Trichoderma brevicompactum.

Authors:  Kristian Fog Nielsen; Tom Gräfenhan; Doustmorad Zafari; Ulf Thrane
Journal:  J Agric Food Chem       Date:  2005-10-19       Impact factor: 5.279

3.  Trichoderma taxi sp. nov., an endophytic fungus from Chinese yew Taxus mairei.

Authors:  Chu-Long Zhang; Shu-Peng Liu; Fu-Cheng Lin; Christian P Kubicek; Irina S Druzhinina
Journal:  FEMS Microbiol Lett       Date:  2007-02-16       Impact factor: 2.742

4.  Dihalogenated trichodermin (4β-acet-oxy-9,10-dibromo-12,13-epoxy-tri-chothec).

Authors:  Jin-Hao Zhao; Yong Zhou; Jian-Gong Zhang; Jing-Li Cheng; Fu-Cheng Lin
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-12-19

5.  Trichodermin (4β-acet-oxy-12,13-epoxy-trichothec-9-ene).

Authors:  Shao-Yuan Chen; Chu-Long Zhang; Yu-Zhe Chen; Fu-Cheng Lin
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-03-12

6.  Trichodermol (4α-hydr-oxy-12,13-epoxy-trichothec-9-ene).

Authors:  Jing-Li Cheng; Yong Zhou; Fu-Cheng Lin; Jin-Hao Zhao; Guo-Nian Zhu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-28

7.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  7 in total
  1 in total

1.  8-{[(E)-3-(2-Chloro-phen-yl)acrylo-yloxy]imino}-12,13-ep-oxy-trichethec-9-en-4-yl (E)-3-(2-chloro-phen-yl)acrylate.

Authors:  Xiao-Jun Xu; Xiao-Liang Li; Jing-Li Cheng; Jin-Hao Zhao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-10-05
  1 in total

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