2-{(1S,2S,4aR,8R,8aR)-8-Hy-droxy-4a,8-dimethyl-1-[(2E)-2-methyl-but-2-eno-yl-oxy]perhydro-naphthalen-2-yl}acrylic acid from Sclerorhachis platyrachis.

The eudesmane-type terpenoid, C(20)H(30)O(5), isolated from Sclerorhachis platyrachis, has a deca-lin skeleton whose six-membered rings adopt chair conformations. The two methyl substituents occupy axial positions, whereas the other three substituents occupy equatorial positions. The hy-droxy group is an intra-molecular hydrogen-bond donor to the single-bond ester O atom; adjacent mol-ecules are linked through the carb-oxy-lic acid interacting with the hydroxyl group, forming a hydrogen-bonded chain running along the c axis.

Related literature

For the crystal structure of epiilic acid, see: Daniewski et al. (1986 ▶). For a review of eudesmane-type sesquiterpenoids, see: Wu et al. (2006 ▶).

Experimental

Crystal data

C20H30O5

M = 350.44

Monoclinic,

a = 6.2718 (1) Å

b = 19.0285 (3) Å

c = 8.4530 (2) Å

β = 110.184 (2)°

V = 946.85 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.71 mm−1

T = 100 K

0.20 × 0.20 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.872, T max = 0.872

5962 measured reflections

3663 independent reflections

3635 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.076

S = 1.03

3663 reflections

238 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.13 e Å−3

Absolute structure: Flack (1983 ▶), 1705 Friedel pairs

Flack parameter: 0.08 (11)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037640/jh2330sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037640/jh2330Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037640/jh2330Isup3.cml

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

C20H30O5	F(000) = 380
Mr = 350.44	Dx = 1.229 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 4968 reflections
a = 6.2718 (1) Å	θ = 5.6–74.1°
b = 19.0285 (3) Å	µ = 0.71 mm−1
c = 8.4530 (2) Å	T = 100 K
β = 110.184 (2)°	Prism, colourless
V = 946.85 (3) Å3	0.20 × 0.20 × 0.20 mm
Z = 2

Agilent SuperNova Dual diffractometer with an Atlas detector	3663 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3635 reflections with I > 2σ(I)
Mirror	Rint = 0.015
Detector resolution: 10.4041 pixels mm-1	θmax = 74.2°, θmin = 5.6°
ω scans	h = −6→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −23→22
Tmin = 0.872, Tmax = 0.872	l = −10→10
5962 measured reflections

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.1079P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3663 reflections	Δρmax = 0.19 e Å−3
238 parameters	Δρmin = −0.13 e Å−3
1 restraint	Absolute structure: Flack (1983), 1705 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (11)

	x	y	z	Uiso*/Ueq
O1	0.94364 (17)	0.50094 (5)	0.32350 (12)	0.0229 (2)
O2	1.0317 (2)	0.39226 (6)	0.42340 (14)	0.0337 (2)
O3	0.88724 (14)	0.44178 (4)	−0.13924 (11)	0.01664 (18)
O4	0.64080 (17)	0.41443 (5)	−0.00727 (13)	0.0264 (2)
O5	0.76555 (15)	0.51072 (5)	−0.43525 (11)	0.01914 (19)
C1	1.0458 (2)	0.43922 (7)	0.33077 (16)	0.0212 (3)
C2	1.1838 (2)	0.43410 (7)	0.21712 (15)	0.0190 (2)
C3	1.3138 (3)	0.37790 (8)	0.2342 (2)	0.0305 (3)
H3A	1.3167	0.3431	0.3155	0.037*
H3B	1.4042	0.3723	0.1651	0.037*
C4	1.1868 (2)	0.49268 (6)	0.09608 (15)	0.0170 (2)
H4	1.2901	0.4766	0.0358	0.020*
C5	1.2922 (2)	0.56070 (7)	0.19001 (15)	0.0200 (3)
H5A	1.2069	0.5752	0.2636	0.024*
H5B	1.4512	0.5514	0.2626	0.024*
C6	1.2884 (2)	0.62031 (7)	0.06860 (16)	0.0199 (3)
H6A	1.3928	0.6086	0.0073	0.024*
H6B	1.3454	0.6637	0.1342	0.024*
C7	1.0501 (2)	0.63443 (6)	−0.06021 (15)	0.0167 (2)
C8	0.8926 (2)	0.65941 (7)	0.03410 (16)	0.0205 (3)
H8A	0.9591	0.7008	0.1024	0.031*
H8B	0.8751	0.6217	0.1075	0.031*
H8C	0.7435	0.6717	−0.0477	0.031*
C9	1.0683 (2)	0.69343 (7)	−0.17927 (17)	0.0198 (3)
H9A	1.1013	0.7383	−0.1162	0.024*
H9B	1.1968	0.6832	−0.2182	0.024*
C10	0.8522 (2)	0.70175 (7)	−0.33205 (16)	0.0205 (3)
H10A	0.7238	0.7141	−0.2946	0.025*
H10B	0.8720	0.7402	−0.4047	0.025*
C11	0.8004 (2)	0.63328 (7)	−0.43153 (15)	0.0196 (3)
H11A	0.9268	0.6226	−0.4726	0.023*
H11B	0.6611	0.6396	−0.5313	0.023*
C12	0.7668 (2)	0.57076 (7)	−0.32876 (14)	0.0165 (2)
C13	0.5355 (2)	0.57294 (7)	−0.30647 (15)	0.0210 (3)
H13A	0.5234	0.5336	−0.2353	0.031*
H13B	0.4151	0.5693	−0.4169	0.031*
H13C	0.5196	0.6173	−0.2529	0.031*
C14	0.97307 (19)	0.56460 (6)	−0.16172 (14)	0.0150 (2)
H14	1.1038	0.5505	−0.1968	0.018*
C15	0.95518 (19)	0.50674 (6)	−0.04079 (14)	0.0144 (2)
H15	0.8402	0.5198	0.0118	0.017*
C16	0.7264 (2)	0.40082 (6)	−0.11125 (15)	0.0178 (2)
C17	0.6621 (2)	0.33936 (6)	−0.22701 (15)	0.0172 (2)
C18	0.7910 (2)	0.32087 (7)	−0.31761 (16)	0.0196 (3)
H18	0.9227	0.3486	−0.3021	0.024*
C19	0.7516 (2)	0.26166 (7)	−0.44010 (17)	0.0249 (3)
H19A	0.8832	0.2301	−0.4053	0.037*
H19B	0.7301	0.2804	−0.5526	0.037*
H19C	0.6156	0.2356	−0.4429	0.037*
C20	0.4449 (2)	0.30420 (7)	−0.23055 (18)	0.0249 (3)
H20A	0.4210	0.2614	−0.2990	0.037*
H20B	0.3170	0.3364	−0.2795	0.037*
H20C	0.4556	0.2920	−0.1154	0.037*
H1	0.881 (4)	0.5016 (12)	0.399 (3)	0.053 (6)*
H5	0.787 (4)	0.4729 (12)	−0.379 (3)	0.041 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0310 (5)	0.0223 (5)	0.0201 (4)	0.0048 (4)	0.0150 (4)	0.0010 (4)
O2	0.0468 (6)	0.0291 (5)	0.0353 (6)	0.0089 (5)	0.0270 (5)	0.0130 (5)
O3	0.0187 (4)	0.0162 (4)	0.0172 (4)	−0.0033 (3)	0.0090 (3)	−0.0039 (3)
O4	0.0302 (5)	0.0262 (5)	0.0305 (5)	−0.0080 (4)	0.0205 (4)	−0.0073 (4)
O5	0.0248 (5)	0.0190 (5)	0.0144 (4)	0.0004 (4)	0.0078 (3)	−0.0025 (4)
C1	0.0245 (6)	0.0220 (6)	0.0178 (6)	0.0016 (5)	0.0082 (5)	0.0016 (5)
C2	0.0211 (5)	0.0192 (6)	0.0170 (5)	−0.0002 (5)	0.0069 (4)	0.0022 (5)
C3	0.0377 (8)	0.0240 (7)	0.0382 (8)	0.0084 (6)	0.0238 (7)	0.0095 (6)
C4	0.0175 (6)	0.0182 (6)	0.0162 (5)	−0.0002 (4)	0.0069 (5)	0.0005 (5)
C5	0.0199 (6)	0.0217 (7)	0.0153 (5)	−0.0035 (5)	0.0019 (4)	0.0003 (5)
C6	0.0185 (6)	0.0209 (6)	0.0194 (6)	−0.0042 (5)	0.0053 (5)	0.0000 (5)
C7	0.0186 (6)	0.0156 (6)	0.0159 (5)	−0.0025 (4)	0.0058 (5)	−0.0017 (4)
C8	0.0244 (6)	0.0189 (6)	0.0193 (6)	−0.0004 (5)	0.0090 (5)	−0.0041 (5)
C9	0.0218 (6)	0.0169 (6)	0.0214 (6)	−0.0017 (4)	0.0083 (5)	0.0003 (4)
C10	0.0252 (6)	0.0161 (6)	0.0207 (6)	0.0034 (5)	0.0084 (5)	0.0027 (5)
C11	0.0220 (6)	0.0212 (6)	0.0150 (6)	0.0017 (5)	0.0057 (5)	0.0010 (5)
C12	0.0184 (6)	0.0170 (6)	0.0147 (5)	0.0011 (5)	0.0063 (4)	−0.0024 (5)
C13	0.0166 (6)	0.0269 (7)	0.0189 (6)	0.0014 (5)	0.0054 (5)	−0.0025 (5)
C14	0.0147 (5)	0.0168 (6)	0.0147 (5)	−0.0004 (4)	0.0067 (4)	−0.0020 (5)
C15	0.0167 (6)	0.0133 (5)	0.0141 (5)	−0.0008 (4)	0.0065 (4)	−0.0027 (4)
C16	0.0161 (5)	0.0196 (6)	0.0186 (6)	−0.0007 (4)	0.0072 (4)	0.0017 (5)
C17	0.0166 (5)	0.0157 (6)	0.0182 (5)	−0.0002 (4)	0.0045 (4)	0.0013 (4)
C18	0.0186 (6)	0.0196 (6)	0.0197 (6)	−0.0010 (5)	0.0054 (5)	−0.0006 (5)
C19	0.0265 (6)	0.0251 (7)	0.0232 (7)	−0.0012 (5)	0.0088 (5)	−0.0056 (5)
C20	0.0199 (6)	0.0232 (7)	0.0333 (7)	−0.0044 (5)	0.0113 (5)	−0.0041 (5)

O1—C1	1.3290 (16)	C9—C10	1.5236 (18)
O1—H1	0.85 (2)	C9—H9A	0.9900
O2—C1	1.2113 (16)	C9—H9B	0.9900
O3—C16	1.3586 (15)	C10—C11	1.5237 (18)
O3—C15	1.4689 (13)	C10—H10A	0.9900
O4—C16	1.2056 (16)	C10—H10B	0.9900
O5—C12	1.4530 (14)	C11—C12	1.5297 (17)
O5—H5	0.85 (2)	C11—H11A	0.9900
C1—C2	1.5021 (17)	C11—H11B	0.9900
C2—C3	1.322 (2)	C12—C13	1.5265 (16)
C2—C4	1.5175 (16)	C12—C14	1.5559 (15)
C3—H3A	0.9500	C13—H13A	0.9800
C3—H3B	0.9500	C13—H13B	0.9800
C4—C15	1.5365 (15)	C13—H13C	0.9800
C4—C5	1.5429 (17)	C14—C15	1.5325 (16)
C4—H4	1.0000	C14—H14	1.0000
C5—C6	1.5245 (17)	C15—H15	1.0000
C5—H5A	0.9900	C16—C17	1.4885 (16)
C5—H5B	0.9900	C17—C18	1.3388 (18)
C6—C7	1.5394 (17)	C17—C20	1.5083 (17)
C6—H6A	0.9900	C18—C19	1.4920 (17)
C6—H6B	0.9900	C18—H18	0.9500
C7—C9	1.5380 (17)	C19—H19A	0.9800
C7—C8	1.5428 (17)	C19—H19B	0.9800
C7—C14	1.5650 (16)	C19—H19C	0.9800
C8—H8A	0.9800	C20—H20A	0.9800
C8—H8B	0.9800	C20—H20B	0.9800
C8—H8C	0.9800	C20—H20C	0.9800
C1—O1—H1	108.4 (15)	H10A—C10—H10B	108.2
C16—O3—C15	118.15 (9)	C10—C11—C12	113.36 (10)
C12—O5—H5	110.5 (14)	C10—C11—H11A	108.9
O2—C1—O1	122.71 (12)	C12—C11—H11A	108.9
O2—C1—C2	123.53 (12)	C10—C11—H11B	108.9
O1—C1—C2	113.74 (11)	C12—C11—H11B	108.9
C3—C2—C1	116.90 (12)	H11A—C11—H11B	107.7
C3—C2—C4	121.14 (12)	O5—C12—C13	107.20 (10)
C1—C2—C4	121.84 (11)	O5—C12—C11	103.42 (9)
C2—C3—H3A	120.0	C13—C12—C11	111.83 (11)
C2—C3—H3B	120.0	O5—C12—C14	109.15 (9)
H3A—C3—H3B	120.0	C13—C12—C14	114.71 (9)
C2—C4—C15	114.03 (10)	C11—C12—C14	109.86 (10)
C2—C4—C5	111.84 (10)	C12—C13—H13A	109.5
C15—C4—C5	111.54 (10)	C12—C13—H13B	109.5
C2—C4—H4	106.3	H13A—C13—H13B	109.5
C15—C4—H4	106.3	C12—C13—H13C	109.5
C5—C4—H4	106.3	H13A—C13—H13C	109.5
C6—C5—C4	111.93 (10)	H13B—C13—H13C	109.5
C6—C5—H5A	109.2	C15—C14—C12	115.48 (9)
C4—C5—H5A	109.2	C15—C14—C7	108.91 (9)
C6—C5—H5B	109.2	C12—C14—C7	115.86 (10)
C4—C5—H5B	109.2	C15—C14—H14	105.1
H5A—C5—H5B	107.9	C12—C14—H14	105.1
C5—C6—C7	113.06 (10)	C7—C14—H14	105.1
C5—C6—H6A	109.0	O3—C15—C14	107.48 (8)
C7—C6—H6A	109.0	O3—C15—C4	107.10 (9)
C5—C6—H6B	109.0	C14—C15—C4	111.08 (9)
C7—C6—H6B	109.0	O3—C15—H15	110.4
H6A—C6—H6B	107.8	C14—C15—H15	110.4
C6—C7—C9	108.48 (10)	C4—C15—H15	110.4
C6—C7—C8	109.08 (10)	O4—C16—O3	123.23 (11)
C9—C7—C8	108.57 (10)	O4—C16—C17	124.06 (11)
C6—C7—C14	106.28 (10)	O3—C16—C17	112.67 (10)
C9—C7—C14	109.85 (9)	C18—C17—C16	120.16 (11)
C8—C7—C14	114.42 (10)	C18—C17—C20	126.28 (12)
C7—C8—H8A	109.5	C16—C17—C20	113.55 (11)
C7—C8—H8B	109.5	C17—C18—C19	127.40 (12)
H8A—C8—H8B	109.5	C17—C18—H18	116.3
C7—C8—H8C	109.5	C19—C18—H18	116.3
H8A—C8—H8C	109.5	C18—C19—H19A	109.5
H8B—C8—H8C	109.5	C18—C19—H19B	109.5
C10—C9—C7	112.67 (10)	H19A—C19—H19B	109.5
C10—C9—H9A	109.1	C18—C19—H19C	109.5
C7—C9—H9A	109.1	H19A—C19—H19C	109.5
C10—C9—H9B	109.1	H19B—C19—H19C	109.5
C7—C9—H9B	109.1	C17—C20—H20A	109.5
H9A—C9—H9B	107.8	C17—C20—H20B	109.5
C11—C10—C9	109.70 (10)	H20A—C20—H20B	109.5
C11—C10—H10A	109.7	C17—C20—H20C	109.5
C9—C10—H10A	109.7	H20A—C20—H20C	109.5
C11—C10—H10B	109.7	H20B—C20—H20C	109.5
C9—C10—H10B	109.7
O2—C1—C2—C3	−7.2 (2)	C13—C12—C14—C7	−79.68 (14)
O1—C1—C2—C3	171.30 (13)	C11—C12—C14—C7	47.30 (13)
O2—C1—C2—C4	176.65 (13)	C6—C7—C14—C15	63.08 (12)
O1—C1—C2—C4	−4.81 (17)	C9—C7—C14—C15	−179.76 (9)
C3—C2—C4—C15	120.75 (14)	C8—C7—C14—C15	−57.36 (13)
C1—C2—C4—C15	−63.31 (15)	C6—C7—C14—C12	−164.75 (10)
C3—C2—C4—C5	−111.53 (15)	C9—C7—C14—C12	−47.59 (13)
C1—C2—C4—C5	64.41 (15)	C8—C7—C14—C12	74.81 (13)
C2—C4—C5—C6	−178.17 (10)	C16—O3—C15—C14	−137.12 (10)
C15—C4—C5—C6	−49.13 (14)	C16—O3—C15—C4	103.46 (11)
C4—C5—C6—C7	53.90 (14)	C12—C14—C15—O3	48.75 (12)
C5—C6—C7—C9	−178.02 (10)	C7—C14—C15—O3	−178.88 (8)
C5—C6—C7—C8	63.89 (13)	C12—C14—C15—C4	165.60 (9)
C5—C6—C7—C14	−59.95 (13)	C7—C14—C15—C4	−62.02 (12)
C6—C7—C9—C10	168.69 (10)	C2—C4—C15—O3	−60.90 (12)
C8—C7—C9—C10	−72.89 (13)	C5—C4—C15—O3	171.23 (9)
C14—C7—C9—C10	52.92 (13)	C2—C4—C15—C14	−177.99 (10)
C7—C9—C10—C11	−59.35 (14)	C5—C4—C15—C14	54.14 (12)
C9—C10—C11—C12	59.45 (14)	C15—O3—C16—O4	−1.68 (17)
C10—C11—C12—O5	−169.09 (10)	C15—O3—C16—C17	176.10 (9)
C10—C11—C12—C13	75.89 (13)	O4—C16—C17—C18	−168.19 (13)
C10—C11—C12—C14	−52.68 (13)	O3—C16—C17—C18	14.06 (16)
O5—C12—C14—C15	−70.92 (12)	O4—C16—C17—C20	12.88 (18)
C13—C12—C14—C15	49.37 (14)	O3—C16—C17—C20	−164.88 (11)
C11—C12—C14—C15	176.34 (9)	C16—C17—C18—C19	−179.39 (12)
O5—C12—C14—C7	160.04 (9)	C20—C17—C18—C19	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5i	0.85 (2)	1.80 (2)	2.648 (1)	174 (2)
O5—H5···O3	0.85 (2)	1.99 (2)	2.692 (1)	139 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5i	0.85 (2)	1.80 (2)	2.648 (1)	174 (2)
O5—H5⋯O3	0.85 (2)	1.99 (2)	2.692 (1)	139 (2)

Symmetry code: (i) .