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

In the title compound, C(15)H(22)O(3), the five-membered ring displays an envelope conformation, whereas the two six-membered rings show different conformations, viz. chair and half-chair. In the crystal, mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For the fungicidal activity of the endophytic fungus Trichoderma taxi sp. nov. from Taxus mairei, see: Nielsen et al. (2005 ▶); Zhang et al. (2007 ▶). For the related Trichodermin structure, see: Chen et al. (2008 ▶). For the extinction correction, see: Larson (1970 ▶).

Experimental

Crystal data

C15H22O3

M = 250.34

Monoclinic,

a = 6.8284 (2) Å

b = 6.6209 (3) Å

c = 14.7170 (6) Å

β = 96.7507 (11)°

V = 660.74 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.66 × 0.49 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.934, T max = 0.976

6503 measured reflections

1634 independent reflections

1540 reflections with F 2 > 2σ(F 2)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.00

1634 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1993 ▶); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996 ▶); 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/S1600536809044080/si2217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044080/si2217Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H22O3	F(000) = 272.00
Mr = 250.34	Dx = 1.258 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2yb	Cell parameters from 6124 reflections
a = 6.8284 (2) Å	θ = 3.0–27.4°
b = 6.6209 (3) Å	µ = 0.09 mm−1
c = 14.7170 (6) Å	T = 296 K
β = 96.7507 (11)°	Chunk, colorless
V = 660.74 (4) Å3	0.66 × 0.49 × 0.28 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	1540 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.018
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→8
Tmin = 0.934, Tmax = 0.976	k = −8→8
6503 measured reflections	l = −19→18
1634 independent reflections

Refinement on F2	w = 1/[0.0012Fo2 + 1.5σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.034	(Δ/σ)max < 0.001
wR(F2) = 0.095	Δρmax = 0.17 e Å−3
S = 1.00	Δρmin = −0.15 e Å−3
1634 reflections	Extinction correction: Larson (1970), equation 22
164 parameters	Extinction coefficient: 184 (28)
H-atom parameters constrained

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
O1	0.84609 (16)	0.3577 (2)	0.83213 (8)	0.0329 (3)
O2	0.9112 (2)	0.9341 (2)	0.83678 (11)	0.0535 (4)
O3	0.44991 (17)	0.5728 (2)	0.95141 (8)	0.0428 (3)
C1	0.8680 (2)	0.4910 (2)	0.75578 (11)	0.0295 (4)
C2	0.9296 (2)	0.3595 (3)	0.68075 (12)	0.0389 (4)
C3	0.8120 (2)	0.3061 (3)	0.60656 (12)	0.0423 (5)
C4	0.5978 (2)	0.3670 (3)	0.59348 (12)	0.0484 (5)
C5	0.5275 (2)	0.4606 (3)	0.67912 (12)	0.0394 (4)
C6	0.6784 (2)	0.6115 (2)	0.72646 (11)	0.0307 (4)
C7	0.6045 (2)	0.7082 (2)	0.81427 (11)	0.0298 (4)
C8	0.7735 (2)	0.8181 (2)	0.87935 (12)	0.0374 (4)
C9	0.8824 (2)	0.6492 (3)	0.93698 (12)	0.0398 (4)
C10	0.7723 (2)	0.4555 (3)	0.90883 (11)	0.0326 (4)
C11	0.5685 (2)	0.5348 (2)	0.87747 (11)	0.0294 (4)
C12	0.3896 (2)	0.4194 (3)	0.88380 (12)	0.0418 (5)
C13	0.8819 (4)	0.1859 (4)	0.52998 (14)	0.0596 (6)
C14	0.7229 (3)	0.7762 (3)	0.65783 (14)	0.0505 (5)
C15	0.4273 (2)	0.8481 (3)	0.79217 (14)	0.0485 (5)
H1	0.9748	0.5866	0.7745	0.035*
H2	1.0589	0.3125	0.6868	0.047*
H8	0.7109	0.9068	0.9207	0.045*
H10	0.7711	0.3629	0.9607	0.039*
H41	0.5787	0.4649	0.5442	0.058*
H42	0.5188	0.2479	0.5769	0.058*
H51	0.4041	0.5308	0.6617	0.047*
H52	0.5066	0.3534	0.7219	0.047*
H91	1.0183	0.6401	0.9241	0.048*
H92	0.8794	0.6749	1.0017	0.048*
H121	0.3980	0.2778	0.9006	0.050*
H122	0.2745	0.4411	0.8396	0.050*
H131	0.8038	0.0656	0.5201	0.072*
H132	1.0178	0.1497	0.5458	0.072*
H133	0.8688	0.2656	0.4751	0.072*
H141	0.7607	0.7139	0.6036	0.061*
H142	0.8285	0.8602	0.6850	0.061*
H143	0.6072	0.8572	0.6421	0.061*
H151	0.3317	0.7839	0.7485	0.058*
H152	0.4697	0.9723	0.7670	0.058*
H153	0.3691	0.8760	0.8471	0.058*
H201	0.8723	1.0539	0.8294	0.066*

	U11	U22	U33	U12	U13	U23
O1	0.0392 (5)	0.0274 (6)	0.0324 (5)	0.0083 (5)	0.0063 (4)	−0.0003 (5)
O2	0.0587 (8)	0.0287 (7)	0.0781 (10)	−0.0102 (7)	0.0296 (7)	−0.0093 (7)
O3	0.0493 (7)	0.0455 (8)	0.0377 (6)	0.0024 (6)	0.0226 (5)	−0.0016 (6)
C1	0.0308 (7)	0.0267 (9)	0.0320 (7)	−0.0024 (6)	0.0076 (5)	−0.0016 (6)
C2	0.0398 (8)	0.0335 (10)	0.0466 (9)	−0.0012 (8)	0.0179 (7)	−0.0075 (8)
C3	0.0633 (10)	0.0326 (10)	0.0344 (9)	−0.0079 (9)	0.0207 (8)	−0.0044 (8)
C4	0.0632 (11)	0.0501 (13)	0.0308 (8)	−0.0053 (11)	0.0004 (7)	−0.0065 (9)
C5	0.0381 (7)	0.0463 (12)	0.0330 (8)	0.0009 (8)	0.0007 (6)	0.0002 (9)
C6	0.0386 (7)	0.0272 (9)	0.0273 (7)	0.0021 (7)	0.0083 (5)	0.0025 (6)
C7	0.0336 (7)	0.0241 (8)	0.0329 (8)	0.0043 (6)	0.0093 (5)	0.0022 (7)
C8	0.0424 (8)	0.0303 (10)	0.0419 (9)	−0.0012 (7)	0.0153 (7)	−0.0106 (8)
C9	0.0393 (8)	0.0459 (11)	0.0337 (8)	0.0021 (8)	0.0023 (6)	−0.0101 (8)
C10	0.0383 (7)	0.0342 (10)	0.0254 (7)	0.0076 (7)	0.0049 (5)	0.0043 (7)
C11	0.0343 (7)	0.0293 (9)	0.0261 (7)	0.0030 (7)	0.0103 (5)	0.0001 (7)
C12	0.0393 (8)	0.0427 (11)	0.0455 (9)	−0.0034 (8)	0.0145 (7)	0.0013 (9)
C13	0.0909 (15)	0.0460 (13)	0.0478 (11)	−0.0127 (13)	0.0322 (11)	−0.0138 (11)
C14	0.0785 (13)	0.0354 (11)	0.0413 (10)	0.0041 (10)	0.0229 (9)	0.0086 (9)
C15	0.0516 (9)	0.0397 (12)	0.0563 (11)	0.0188 (10)	0.0144 (8)	0.0089 (10)

O1—C1	1.450 (2)	C1—H1	0.980
O1—C10	1.443 (2)	C2—H2	0.930
O2—C8	1.416 (2)	C4—H41	0.970
O3—C11	1.453 (2)	C4—H42	0.970
O3—C12	1.447 (2)	C5—H51	0.970
C1—C2	1.504 (2)	C5—H52	0.970
C1—C6	1.539 (2)	C8—H8	0.980
C2—C3	1.325 (2)	C9—H91	0.970
C3—C4	1.508 (2)	C9—H92	0.970
C3—C13	1.503 (3)	C10—H10	0.980
C4—C5	1.531 (2)	C12—H121	0.970
C5—C6	1.542 (2)	C12—H122	0.970
C6—C7	1.577 (2)	C13—H131	0.960
C6—C14	1.541 (2)	C13—H132	0.960
C7—C8	1.587 (2)	C13—H133	0.960
C7—C11	1.516 (2)	C14—H141	0.960
C7—C15	1.528 (2)	C14—H142	0.960
C8—C9	1.541 (2)	C14—H143	0.960
C9—C10	1.520 (2)	C15—H151	0.960
C10—C11	1.508 (2)	C15—H152	0.960
C11—C12	1.453 (2)	C15—H153	0.960
O2—H201	0.840
C1—O1—C10	114.24 (13)	C3—C4—H42	108.5
C11—O3—C12	60.14 (11)	C5—C4—H41	108.5
O1—C1—C2	106.26 (14)	C5—C4—H42	108.5
O1—C1—C6	111.87 (12)	H41—C4—H42	109.5
C2—C1—C6	113.14 (12)	C4—C5—H51	108.8
C1—C2—C3	124.36 (16)	C4—C5—H52	108.8
C2—C3—C4	121.26 (18)	C6—C5—H51	108.8
C2—C3—C13	122.95 (18)	C6—C5—H52	108.8
C4—C3—C13	115.78 (17)	H51—C5—H52	109.5
C3—C4—C5	113.36 (15)	O2—C8—H8	108.1
C4—C5—C6	112.11 (15)	C7—C8—H8	108.1
C1—C6—C5	106.63 (14)	C9—C8—H8	108.1
C1—C6—C7	108.69 (12)	C8—C9—H91	110.4
C1—C6—C14	109.07 (15)	C8—C9—H92	110.4
C5—C6—C7	111.85 (13)	C10—C9—H91	110.4
C5—C6—C14	109.60 (14)	C10—C9—H92	110.4
C7—C6—C14	110.88 (15)	H91—C9—H92	109.5
C6—C7—C8	113.63 (13)	O1—C10—H10	111.4
C6—C7—C11	106.61 (14)	C9—C10—H10	111.4
C6—C7—C15	113.16 (13)	C11—C10—H10	111.4
C8—C7—C11	97.80 (12)	O3—C12—H121	120.0
C8—C7—C15	110.62 (15)	O3—C12—H122	120.0
C11—C7—C15	114.07 (14)	C11—C12—H121	120.0
O2—C8—C7	117.07 (15)	C11—C12—H122	120.0
O2—C8—C9	109.54 (14)	H121—C12—H122	109.5
C7—C8—C9	105.64 (15)	C3—C13—H131	109.5
C8—C9—C10	105.72 (13)	C3—C13—H132	109.5
O1—C10—C9	112.64 (14)	C3—C13—H133	109.5
O1—C10—C11	108.15 (12)	H131—C13—H132	109.5
C9—C10—C11	101.46 (15)	H131—C13—H133	109.5
O3—C11—C7	118.26 (15)	H132—C13—H133	109.5
O3—C11—C10	113.99 (12)	C6—C14—H141	109.5
O3—C11—C12	59.75 (11)	C6—C14—H142	109.5
C7—C11—C10	103.95 (13)	C6—C14—H143	109.5
C7—C11—C12	129.49 (14)	H141—C14—H142	109.5
C10—C11—C12	123.35 (16)	H141—C14—H143	109.5
O3—C12—C11	60.11 (11)	H142—C14—H143	109.5
C8—O2—H201	110.7	C7—C15—H151	109.5
O1—C1—H1	108.5	C7—C15—H152	109.5
C2—C1—H1	108.5	C7—C15—H153	109.5
C6—C1—H1	108.5	H151—C15—H152	109.5
C1—C2—H2	117.8	H151—C15—H153	109.5
C3—C2—H2	117.8	H152—C15—H153	109.5
C3—C4—H41	108.5
C1—O1—C10—C9	−48.89 (16)	C14—C6—C7—C11	−179.10 (14)
C1—O1—C10—C11	62.42 (17)	C14—C6—C7—C15	54.7 (2)
C10—O1—C1—C2	−175.48 (11)	C6—C7—C8—O2	40.8 (2)
C10—O1—C1—C6	−51.55 (16)	C6—C7—C8—C9	−81.40 (17)
C12—O3—C11—C7	121.49 (16)	C6—C7—C11—O3	−163.39 (12)
C12—O3—C11—C10	−115.92 (18)	C6—C7—C11—C10	69.08 (15)
O1—C1—C2—C3	105.4 (2)	C6—C7—C11—C12	−90.7 (2)
O1—C1—C6—C5	−71.96 (16)	C8—C7—C11—O3	79.03 (15)
O1—C1—C6—C7	48.78 (17)	C8—C7—C11—C10	−48.50 (15)
O1—C1—C6—C14	169.78 (14)	C8—C7—C11—C12	151.67 (18)
C2—C1—C6—C5	48.01 (18)	C11—C7—C8—O2	152.82 (15)
C2—C1—C6—C7	168.75 (14)	C11—C7—C8—C9	30.61 (16)
C2—C1—C6—C14	−70.25 (19)	C15—C7—C8—O2	−87.74 (19)
C6—C1—C2—C3	−17.7 (2)	C15—C7—C8—C9	150.05 (15)
C1—C2—C3—C4	−3.0 (3)	C15—C7—C11—O3	−37.8 (2)
C1—C2—C3—C13	175.8 (2)	C15—C7—C11—C10	−165.28 (15)
C2—C3—C4—C5	−9.8 (3)	C15—C7—C11—C12	34.9 (2)
C13—C3—C4—C5	171.3 (2)	O2—C8—C9—C10	−129.73 (15)
C3—C4—C5—C6	43.1 (2)	C7—C8—C9—C10	−2.80 (18)
C4—C5—C6—C1	−61.64 (19)	C8—C9—C10—O1	88.78 (16)
C4—C5—C6—C7	179.67 (15)	C8—C9—C10—C11	−26.62 (17)
C4—C5—C6—C14	56.3 (2)	O1—C10—C11—O3	159.65 (14)
C1—C6—C7—C8	47.34 (19)	O1—C10—C11—C7	−70.22 (17)
C1—C6—C7—C11	−59.22 (16)	O1—C10—C11—C12	91.20 (19)
C1—C6—C7—C15	174.58 (15)	C9—C10—C11—O3	−81.67 (17)
C5—C6—C7—C8	164.80 (14)	C9—C10—C11—C7	48.45 (16)
C5—C6—C7—C11	58.24 (16)	C9—C10—C11—C12	−150.13 (16)
C5—C6—C7—C15	−68.0 (2)	C7—C11—C12—O3	−103.3 (2)
C14—C6—C7—C8	−72.54 (18)	C10—C11—C12—O3	100.35 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H201···O1i	0.84	2.02	2.839 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H201⋯O1i	0.84	2.02	2.839 (2)	165

Symmetry code: (i) .