2-{(1S,2S,4aR,8R,8aR)-8-Hy­droxy-4a,8-dimethyl-1-[(2E)-2-methyl­but-2-eno­yl­oxy]perhydro­naphthalen-2-yl}acrylic acid from Sclerorhachis platyrachis

Kheyrabadi, R.; Habibi, Z.; Ng, S.W.

doi:10.1107/S1600536811037640

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2699

https://doi.org/10.1107/S1600536811037640

Open

access

2-{(1S,2S,4aR,8R,8aR)-8-Hydroxy-4a,8-dimethyl-1-[(2E)-2-methylbut-2-enoyloxy]perhydronaphthalen-2-yl}acrylic acid from Sclerorhachis platyrachis

Rasool Kheyrabadi,^a Zohreh Habibi ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, Shahid Beheshti University, General Campus, Tehran, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 13 September 2011; accepted 15 September 2011; online 30 September 2011)

The eudesmane-type terpenoid, C₂₀H₃₀O₅, isolated from Sclerorhachis platyrachis, has a decalin skeleton whose six-membered rings adopt chair conformations. The two methyl substituents occupy axial positions, whereas the other three substituents occupy equatorial positions. The hydroxy group is an intramolecular hydrogen-bond donor to the single-bond ester O atom; adjacent molecules are linked through the carboxylic 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_r = 350.44
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.076
S = 1.03
3663 reflections
238 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ), 1705 Friedel pairs
Flack parameter: 0.08 (11)

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) x, y, z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037640/jh2330sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037640/jh2330Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037640/jh2330Isup3.cml

checkCIF report

Comment top

Eudesmane-type of sesquiterpenoids (from the Asteraceae family) have been reviewed; some structural assignments and stereochemistries have also revised; however, the title compound (Scheme I) is not included in the review (Wu et al., 2006). The compound is a derivative of epiilic (vachanic) acid having a 1-(2-methylbut-2-enoyloxy) substitutent. The crystal structure of the parent acid itself, which was first isolated from Dittrichia vicossa (L.), has been reported (Daniewski et al., 186). The two methyl substituents occupy axial positions whereas the other three substituents occupy equatorial positions (Fig 1). The hydroxy group is an intramolecular hydrogen-bond donor to the single-bond ester O atom; adjacent molecules are linked through the carboxylic acid portion to form a hydrogen-bonded chain running along the c-axis of the monoclinic unit cell (Table 1).

Related literature top

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 top

The leaves and stems of Sclerorhachis platyrachis (Compositae family) were collected from Sabzevar, Khorasan Razavi Province, Iran, at the flowering stage of the plant, i.e., around May. The aerial parts were dried in the shade. The aerial parts (300 g) were extracted with chloroform by maceration at room temperature. The extract was concentrated to a green gummy extract (16 g). The extract was subjected to column chromatography on silica gel (4×70 cm, 70–230 mesh) with a gradient of n-hexane–ethyl acetate and then methanol as eluent. Eighty-three fractions were collected according to TLC analysis and those giving similar spots were combined. Fraction 51 (n-hexane: ethylacetate 4:1) afforded colorless crystals of the title compound (500 mg).

Structure description top

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

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₀H₃₀O₅ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain structure.

2-{(1S,2S,4aR,8R,8aR)-8-Hydroxy- 4a,8-dimethyl-1-[(2E)-2-methylbut-2-enoyloxy]decahydronaphthalen- 2-yl}acrylic acid top

Crystal data top

C₂₀H₃₀O₅	F(000) = 380
M_r = 350.44	D_x = 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

Data collection top

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 monochromator	R_int = 0.015
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.2°, θ_min = 5.6°
ω scans	h = −6→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −23→22
T_min = 0.872, T_max = 0.872	l = −10→10
5962 measured reflections

Refinement top

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(F_o²) + (0.0493P)² + 0.1079P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3663 reflections	Δρ_max = 0.19 e Å⁻³
238 parameters	Δρ_min = −0.13 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1705 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (11)

Crystal data top

C₂₀H₃₀O₅	V = 946.85 (3) Å³
M_r = 350.44	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 6.2718 (1) Å	µ = 0.71 mm⁻¹
b = 19.0285 (3) Å	T = 100 K
c = 8.4530 (2) Å	0.20 × 0.20 × 0.20 mm
β = 110.184 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3663 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3635 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.872	R_int = 0.015
5962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.076	Δρ_max = 0.19 e Å⁻³
S = 1.03	Δρ_min = −0.13 e Å⁻³
3663 reflections	Absolute structure: Flack (1983), 1705 Friedel pairs
238 parameters	Absolute structure parameter: 0.08 (11)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₃₀O₅
M_r	350.44
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	6.2718 (1), 19.0285 (3), 8.4530 (2)
β (°)	110.184 (2)
V (Å³)	946.85 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.872, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	5962, 3663, 3635
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.076, 1.03
No. of reflections	3663
No. of parameters	238
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.13
Absolute structure	Flack (1983), 1705 Friedel pairs
Absolute structure parameter	0.08 (11)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x, y, z+1.

Acknowledgements

The authors thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Daniewski, W. M., Kroszcznski, W., Bloszyk, E., Drozdz, B., Nawrot, J., Rychlewska, U., Budesinsky, M. & Holub, M. (1986). Collect. Czech. Chem. Commun. 51, 1710–1721. CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, Q.-X., Shi, Y.-P. & Jia, Z.-J. (2006). Nat. Prod. Rep. 23, 699–734. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2699

https://doi.org/10.1107/S1600536811037640

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-{(1S,2S,4aR,8R,8aR)-8-Hy­dr­oxy-4a,8-di­methyl-1-[(2E)-2-methyl­but-2-eno­yl­­oxy]perhydro­naphthalen-2-yl}acrylic acid from Sclerorhachis platyrachis

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{(1S,2S,4aR,8R,8aR)-8-Hydroxy-4a,8-dimethyl-1-[(2E)-2-methylbut-2-enoyloxy]perhydronaphthalen-2-yl}acrylic acid from Sclerorhachis platyrachis