14-Hy­droxy-8,14-secogammacera-7-ene-3,21-dione from the bark of Lansium domesticum Corr.

Supratman, U.; Mayanti, T.; Awang, K.; Mukhtar, M.R.; Ng, S.W.

doi:10.1107/S1600536810021136

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1621

doi:10.1107/S1600536810021136

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14-Hydroxy-8,14-secogammacera-7-ene-3,21-dione from the bark of Lansium domesticum Corr.

Unang Supratman,^a Tri Mayanti,^a Khalijah Awang,^b Mat Ropi Mukhtar ^b and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jatinangor 45363, Indonesia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 2 June 2010; accepted 3 June 2010; online 9 June 2010)

In the title compound (kokosanolide B), C₃₀H₄₈O₃, the hexahydro- and octahydronaphthalen-2-one ring systems are connected through an ethylene fragment, with a C—CH₂—CH₂—C torsion angle of 176.2 (2)°. The cyclohexene ring adopts a half-chair conformation, while the other six-membered rings adopt distorted chair conformations. In the crystal, adjacent molecules are linked into a zigzag chain along the b axis by O—H⋯O hydrogen bonds involving the hydroxy and carbonyl groups.

Related literature

For a related compound from the same species, see: Tjokronegero et al. (2009 ). For kokosanolide A, see: Mayanti et al. (2009 ).

Experimental

Crystal data

C₃₀H₄₈O₃
M_r = 456.68
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.8841 (11) Å
b = 14.8301 (13) Å
c = 15.2755 (13) Å
V = 2692.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.20 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEXII diffractometer
26171 measured reflections
3469 independent reflections
3033 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.098
S = 1.01
3469 reflections
310 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.84 (1)	2.15 (1)	2.974 (2)	167 (3)
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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: 10.1107/S1600536810021136/ci5095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021136/ci5095Isup2.hkl

checkCIF report

Comment top

A previous study on the bark of Lansium domesticum Corr (Meliaceae) yielded a co-crystal, 8,14-secogammacera-7,14 (27)-diene–3,21-dione-8,14-secogammacera-7,14-diene-3,21-dione (1.5/0.5). The major component has an excocyclic double bond and an endocyclic double bond (Tjokronegero et al., 2009). In the present compound (Scheme I), a molecule of water has been added across the endocyclic double bond to furnish the corresponding alcohol (Fig. 1).

The hexahydro-naphthalen-2-one and octahydro-naphthalen-2-one ring systems are connected through an ethylene fragment, with a C–CH₂–CH₂–C torsion angle of 176.2 (2)°. The hydroxy unit of one fused-ring forms a hydrogen bond to the ketonic unit of the other fused-ring of an adjacent molecule to generate a zigzag chain.

Related literature top

For a related compound from the same species, see: Tjokronegero et al. (2009). For kokosanolide A, see: Mayanti et al. (2009).

Experimental top

Lansium domesticum Corr. (Meliaceae) was collected in Cililin, Bandung, Indonesia, in 2006. The plant was identified by the staff at Department of Biology, Padjadjaran University. The dried and milled bark of L. domesticum (3 kg) was extracted exhaustively by methanol at room temperature. The methanol extract (250 g) was partitioned between n-hexane and ethyl acetate to give an n-hexane soluble fraction (70 g) and an ethyl acetate soluble fraction (40 g). The ethyl acetate fraction was subjected to vacuum column chromatography on silica gel 60 by using a step gradient of n-hexane/ethyl acetate/methanol. The fraction eluted by n-hexane/ethyl acetate (80:20) was further separated by column chromatography on silica gel n-hexane/ethyl acetate (95:5) and n-hexane/acetone (90:10). Single crystals were obtained by slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. Displacement ellipsoid plot (Barbour, 2001) of C₃₀H₄₈O₃ at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.

14-Hydroxy-8,14-secogammacera-7-ene-3,21-dione top

Crystal data top

C₃₀H₄₈O₃	F(000) = 1008
M_r = 456.68	D_x = 1.127 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3379 reflections
a = 11.8841 (11) Å	θ = 2.6–20.6°
b = 14.8301 (13) Å	µ = 0.07 mm⁻¹
c = 15.2755 (13) Å	T = 100 K
V = 2692.2 (4) Å³	Plate, colourless
Z = 4	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker SMART APEXII diffractometer	3033 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.067
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
ω scans	h = −15→15
26171 measured reflections	k = −17→19
3469 independent reflections	l = −19→19

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0534P)² + 0.4471P] where P = (F_o² + 2F_c²)/3
3469 reflections	(Δ/σ)_max = 0.001
310 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₃₀H₄₈O₃	V = 2692.2 (4) Å³
M_r = 456.68	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.8841 (11) Å	µ = 0.07 mm⁻¹
b = 14.8301 (13) Å	T = 100 K
c = 15.2755 (13) Å	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker SMART APEXII diffractometer	3033 reflections with I > 2σ(I)
26171 measured reflections	R_int = 0.067
3469 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.25 e Å⁻³
3469 reflections	Δρ_min = −0.20 e Å⁻³
310 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.85660 (14)	0.46079 (11)	1.07799 (11)	0.0313 (4)
O2	0.92757 (12)	0.95328 (10)	1.00483 (10)	0.0193 (3)
H2	0.956 (2)	0.9990 (13)	1.0283 (17)	0.044 (9)*
O3	0.97661 (13)	0.62965 (10)	0.44013 (10)	0.0230 (3)
C1	1.00012 (16)	0.70418 (13)	0.99742 (13)	0.0139 (4)
C2	0.94385 (17)	0.63545 (13)	0.93607 (13)	0.0171 (4)
H2A	0.8627	0.6497	0.9315	0.021*
H2B	0.9770	0.6414	0.8769	0.021*
C3	0.95721 (19)	0.53755 (14)	0.96705 (14)	0.0205 (5)
H3A	0.9141	0.4974	0.9276	0.025*
H3B	1.0375	0.5202	0.9632	0.025*
C4	0.91696 (17)	0.52388 (14)	1.05964 (15)	0.0190 (4)
C5	0.95844 (18)	0.59017 (14)	1.12907 (14)	0.0188 (4)
C6	0.95358 (17)	0.68799 (13)	1.09158 (13)	0.0155 (4)
H6	0.8714	0.7017	1.0870	0.019*
C7	1.07759 (19)	0.55946 (15)	1.15649 (15)	0.0234 (5)
H7A	1.0735	0.4990	1.1822	0.035*
H7B	1.1081	0.6017	1.1997	0.035*
H7C	1.1267	0.5582	1.1049	0.035*
C8	0.8817 (2)	0.58287 (17)	1.20997 (15)	0.0296 (5)
H8A	0.8724	0.5193	1.2259	0.044*
H8B	0.8080	0.6091	1.1965	0.044*
H8C	0.9158	0.6156	1.2590	0.044*
C9	1.12928 (17)	0.69324 (14)	0.98960 (14)	0.0185 (4)
H9A	1.1478	0.6293	0.9820	0.028*
H9B	1.1653	0.7160	1.0429	0.028*
H9C	1.1565	0.7275	0.9390	0.028*
C10	0.99922 (19)	0.75933 (14)	1.15478 (13)	0.0199 (4)
H10A	0.9721	0.7465	1.2148	0.024*
H10B	1.0825	0.7571	1.1553	0.024*
C11	0.96049 (19)	0.85294 (14)	1.12704 (14)	0.0204 (4)
H11A	0.9925	0.8980	1.1679	0.025*
H11B	0.8775	0.8561	1.1318	0.025*
C12	0.99487 (18)	0.87777 (13)	1.03345 (13)	0.0162 (4)
C13	0.96039 (16)	0.80090 (13)	0.97016 (12)	0.0133 (4)
H13	0.8765	0.7983	0.9749	0.016*
C14	1.11914 (18)	0.90456 (14)	1.03022 (15)	0.0212 (5)
H14A	1.1428	0.9110	0.9691	0.032*
H14B	1.1645	0.8578	1.0587	0.032*
H14C	1.1296	0.9620	1.0608	0.032*
C15	0.98231 (16)	0.82616 (14)	0.87297 (13)	0.0160 (4)
H15A	1.0086	0.8894	0.8698	0.019*
H15B	1.0428	0.7872	0.8495	0.019*
C16	0.87697 (17)	0.81557 (14)	0.81600 (13)	0.0159 (4)
H16A	0.8152	0.8511	0.8425	0.019*
H16B	0.8539	0.7514	0.8166	0.019*
C17	0.89186 (16)	0.84596 (14)	0.71915 (12)	0.0152 (4)
H17	0.9747	0.8520	0.7092	0.018*
C18	0.84100 (17)	0.93890 (14)	0.70231 (13)	0.0168 (4)
C19	0.78520 (18)	0.95775 (14)	0.62919 (14)	0.0184 (4)
H19	0.7511	1.0155	0.6245	0.022*
C20	0.77245 (18)	0.89399 (14)	0.55361 (13)	0.0178 (4)
H20A	0.7846	0.9270	0.4981	0.021*
H20B	0.6950	0.8694	0.5530	0.021*
C21	0.85675 (16)	0.81635 (13)	0.56021 (13)	0.0138 (4)
H21	0.9325	0.8456	0.5579	0.017*
C22	0.84927 (16)	0.77380 (13)	0.65296 (13)	0.0133 (4)
C23	0.8624 (2)	1.01122 (15)	0.76957 (15)	0.0237 (5)
H23A	0.8226	1.0664	0.7527	0.036*
H23B	0.9434	1.0234	0.7729	0.036*
H23C	0.8353	0.9909	0.8268	0.036*
C24	0.72842 (17)	0.74445 (14)	0.67586 (13)	0.0165 (4)
H24A	0.7286	0.7126	0.7321	0.025*
H24B	0.6998	0.7043	0.6300	0.025*
H24C	0.6801	0.7978	0.6801	0.025*
C25	0.92925 (17)	0.69270 (14)	0.65756 (13)	0.0171 (4)
H25A	1.0077	0.7143	0.6521	0.021*
H25B	0.9214	0.6635	0.7155	0.021*
C26	0.90659 (19)	0.62292 (14)	0.58610 (13)	0.0194 (4)
H26A	0.9602	0.5722	0.5922	0.023*
H26B	0.8295	0.5987	0.5929	0.023*
C27	0.91895 (17)	0.66457 (14)	0.49686 (13)	0.0166 (4)
C28	0.85347 (18)	0.75171 (14)	0.47911 (12)	0.0163 (4)
C29	0.73416 (19)	0.72086 (16)	0.45128 (14)	0.0226 (5)
H29A	0.7391	0.6859	0.3970	0.034*
H29B	0.6865	0.7739	0.4418	0.034*
H29C	0.7014	0.6833	0.4975	0.034*
C30	0.9062 (2)	0.80059 (15)	0.40058 (14)	0.0240 (5)
H30A	0.9083	0.7598	0.3501	0.036*
H30B	0.9830	0.8193	0.4154	0.036*
H30C	0.8611	0.8538	0.3861	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0368 (9)	0.0232 (9)	0.0339 (10)	−0.0136 (8)	−0.0019 (8)	0.0039 (7)
O2	0.0229 (8)	0.0134 (7)	0.0215 (8)	0.0024 (6)	−0.0014 (6)	−0.0003 (6)
O3	0.0264 (8)	0.0221 (8)	0.0205 (8)	0.0031 (7)	0.0032 (7)	−0.0024 (7)
C1	0.0152 (9)	0.0139 (10)	0.0125 (9)	−0.0004 (8)	0.0005 (8)	−0.0016 (8)
C2	0.0207 (9)	0.0159 (10)	0.0148 (10)	−0.0006 (8)	−0.0008 (8)	−0.0018 (8)
C3	0.0266 (11)	0.0153 (10)	0.0195 (10)	−0.0006 (9)	−0.0009 (9)	−0.0049 (8)
C4	0.0173 (9)	0.0163 (10)	0.0234 (11)	0.0010 (8)	−0.0042 (9)	0.0012 (9)
C5	0.0233 (11)	0.0160 (10)	0.0171 (10)	0.0011 (8)	0.0001 (9)	0.0032 (8)
C6	0.0175 (9)	0.0147 (9)	0.0142 (9)	0.0007 (8)	−0.0008 (8)	0.0004 (8)
C7	0.0302 (11)	0.0168 (10)	0.0232 (11)	0.0001 (10)	−0.0095 (10)	0.0006 (9)
C8	0.0416 (14)	0.0241 (12)	0.0230 (12)	−0.0026 (11)	0.0101 (11)	0.0047 (10)
C9	0.0168 (9)	0.0185 (10)	0.0203 (10)	0.0013 (8)	−0.0009 (8)	−0.0004 (9)
C10	0.0282 (11)	0.0168 (10)	0.0146 (10)	−0.0029 (9)	−0.0019 (9)	−0.0017 (8)
C11	0.0296 (11)	0.0157 (10)	0.0160 (10)	0.0018 (9)	0.0005 (9)	−0.0032 (8)
C12	0.0198 (10)	0.0129 (10)	0.0159 (10)	0.0022 (8)	−0.0011 (8)	−0.0004 (8)
C13	0.0138 (9)	0.0137 (10)	0.0124 (9)	−0.0008 (8)	−0.0008 (7)	−0.0006 (8)
C14	0.0209 (10)	0.0169 (10)	0.0257 (11)	−0.0029 (8)	−0.0066 (9)	−0.0010 (9)
C15	0.0152 (9)	0.0181 (10)	0.0146 (10)	−0.0016 (8)	0.0006 (8)	0.0010 (8)
C16	0.0172 (9)	0.0155 (10)	0.0149 (9)	−0.0016 (8)	−0.0004 (8)	0.0004 (8)
C17	0.0159 (9)	0.0158 (10)	0.0139 (9)	−0.0008 (8)	−0.0003 (8)	0.0015 (8)
C18	0.0189 (9)	0.0133 (10)	0.0182 (10)	−0.0013 (8)	0.0041 (8)	−0.0009 (8)
C19	0.0211 (10)	0.0134 (10)	0.0208 (11)	0.0027 (8)	0.0032 (8)	−0.0002 (8)
C20	0.0224 (10)	0.0163 (10)	0.0146 (10)	0.0029 (8)	−0.0013 (8)	−0.0003 (8)
C21	0.0151 (9)	0.0136 (10)	0.0128 (9)	−0.0013 (8)	0.0005 (8)	0.0002 (8)
C22	0.0135 (9)	0.0124 (9)	0.0140 (9)	−0.0002 (7)	−0.0005 (8)	0.0003 (8)
C23	0.0336 (12)	0.0156 (11)	0.0220 (11)	−0.0013 (9)	−0.0010 (10)	−0.0029 (9)
C24	0.0182 (9)	0.0184 (10)	0.0129 (9)	−0.0033 (8)	0.0015 (8)	0.0001 (8)
C25	0.0198 (10)	0.0181 (10)	0.0134 (9)	0.0022 (8)	−0.0005 (8)	0.0009 (8)
C26	0.0264 (11)	0.0133 (10)	0.0187 (11)	0.0031 (9)	0.0011 (9)	0.0011 (8)
C27	0.0182 (9)	0.0150 (10)	0.0166 (10)	−0.0030 (8)	0.0001 (8)	−0.0031 (8)
C28	0.0198 (10)	0.0161 (10)	0.0130 (10)	−0.0006 (8)	0.0009 (8)	−0.0001 (8)
C29	0.0249 (11)	0.0232 (11)	0.0195 (11)	−0.0003 (9)	−0.0051 (9)	−0.0027 (9)
C30	0.0366 (12)	0.0191 (11)	0.0164 (10)	−0.0002 (10)	0.0065 (9)	0.0010 (9)

Geometric parameters (Å, º) top

O1—C4	1.212 (3)	C15—C16	1.533 (3)
O2—C12	1.444 (2)	C15—H15A	0.99
O2—H2	0.841 (10)	C15—H15B	0.99
O3—C27	1.220 (2)	C16—C17	1.557 (3)
C1—C2	1.538 (3)	C16—H16A	0.99
C1—C9	1.548 (3)	C16—H16B	0.99
C1—C6	1.560 (3)	C17—C18	1.527 (3)
C1—C13	1.566 (3)	C17—C22	1.557 (3)
C2—C3	1.535 (3)	C17—H17	1.00
C2—H2A	0.99	C18—C19	1.329 (3)
C2—H2B	0.99	C18—C23	1.507 (3)
C3—C4	1.507 (3)	C19—C20	1.500 (3)
C3—H3A	0.99	C19—H19	0.95
C3—H3B	0.99	C20—C21	1.530 (3)
C4—C5	1.528 (3)	C20—H20A	0.99
C5—C8	1.540 (3)	C20—H20B	0.99
C5—C7	1.545 (3)	C21—C22	1.553 (3)
C5—C6	1.561 (3)	C21—C28	1.567 (3)
C6—C10	1.531 (3)	C21—H21	1.00
C6—H6	1.00	C22—C25	1.535 (3)
C7—H7A	0.98	C22—C24	1.541 (3)
C7—H7B	0.98	C23—H23A	0.98
C7—H7C	0.98	C23—H23B	0.98
C8—H8A	0.98	C23—H23C	0.98
C8—H8B	0.98	C24—H24A	0.98
C8—H8C	0.98	C24—H24B	0.98
C9—H9A	0.98	C24—H24C	0.98
C9—H9B	0.98	C25—C26	1.528 (3)
C9—H9C	0.98	C25—H25A	0.99
C10—C11	1.523 (3)	C25—H25B	0.99
C10—H10A	0.99	C26—C27	1.504 (3)
C10—H10B	0.99	C26—H26A	0.99
C11—C12	1.532 (3)	C26—H26B	0.99
C11—H11A	0.99	C27—C28	1.533 (3)
C11—H11B	0.99	C28—C30	1.535 (3)
C12—C14	1.530 (3)	C28—C29	1.549 (3)
C12—C13	1.550 (3)	C29—H29A	0.98
C13—C15	1.553 (3)	C29—H29B	0.98
C13—H13	1.00	C29—H29C	0.98
C14—H14A	0.98	C30—H30A	0.98
C14—H14B	0.98	C30—H30B	0.98
C14—H14C	0.98	C30—H30C	0.98

C12—O2—H2	106 (2)	C16—C15—H15B	109.1
C2—C1—C9	108.35 (16)	C13—C15—H15B	109.1
C2—C1—C6	107.81 (16)	H15A—C15—H15B	107.9
C9—C1—C6	113.99 (17)	C15—C16—C17	114.65 (16)
C2—C1—C13	108.29 (16)	C15—C16—H16A	108.6
C9—C1—C13	111.98 (16)	C17—C16—H16A	108.6
C6—C1—C13	106.21 (15)	C15—C16—H16B	108.6
C3—C2—C1	113.21 (17)	C17—C16—H16B	108.6
C3—C2—H2A	108.9	H16A—C16—H16B	107.6
C1—C2—H2A	108.9	C18—C17—C22	112.49 (16)
C3—C2—H2B	108.9	C18—C17—C16	112.11 (16)
C1—C2—H2B	108.9	C22—C17—C16	112.41 (16)
H2A—C2—H2B	107.8	C18—C17—H17	106.4
C4—C3—C2	112.56 (18)	C22—C17—H17	106.4
C4—C3—H3A	109.1	C16—C17—H17	106.4
C2—C3—H3A	109.1	C19—C18—C23	120.51 (19)
C4—C3—H3B	109.1	C19—C18—C17	121.94 (19)
C2—C3—H3B	109.1	C23—C18—C17	117.44 (18)
H3A—C3—H3B	107.8	C18—C19—C20	124.39 (19)
O1—C4—C3	120.6 (2)	C18—C19—H19	117.8
O1—C4—C5	121.8 (2)	C20—C19—H19	117.8
C3—C4—C5	117.56 (18)	C19—C20—C21	110.95 (17)
C4—C5—C8	108.71 (18)	C19—C20—H20A	109.4
C4—C5—C7	107.11 (17)	C21—C20—H20A	109.4
C8—C5—C7	107.74 (18)	C19—C20—H20B	109.4
C4—C5—C6	109.35 (17)	C21—C20—H20B	109.4
C8—C5—C6	109.75 (18)	H20A—C20—H20B	108.0
C7—C5—C6	114.03 (18)	C20—C21—C22	109.17 (16)
C10—C6—C1	110.45 (16)	C20—C21—C28	113.08 (16)
C10—C6—C5	113.44 (17)	C22—C21—C28	118.11 (16)
C1—C6—C5	117.93 (17)	C20—C21—H21	105.1
C10—C6—H6	104.5	C22—C21—H21	105.1
C1—C6—H6	104.5	C28—C21—H21	105.1
C5—C6—H6	104.5	C25—C22—C24	110.21 (16)
C5—C7—H7A	109.5	C25—C22—C21	108.94 (16)
C5—C7—H7B	109.5	C24—C22—C21	112.03 (16)
H7A—C7—H7B	109.5	C25—C22—C17	107.92 (16)
C5—C7—H7C	109.5	C24—C22—C17	110.47 (16)
H7A—C7—H7C	109.5	C21—C22—C17	107.13 (15)
H7B—C7—H7C	109.5	C18—C23—H23A	109.5
C5—C8—H8A	109.5	C18—C23—H23B	109.5
C5—C8—H8B	109.5	H23A—C23—H23B	109.5
H8A—C8—H8B	109.5	C18—C23—H23C	109.5
C5—C8—H8C	109.5	H23A—C23—H23C	109.5
H8A—C8—H8C	109.5	H23B—C23—H23C	109.5
H8B—C8—H8C	109.5	C22—C24—H24A	109.5
C1—C9—H9A	109.5	C22—C24—H24B	109.5
C1—C9—H9B	109.5	H24A—C24—H24B	109.5
H9A—C9—H9B	109.5	C22—C24—H24C	109.5
C1—C9—H9C	109.5	H24A—C24—H24C	109.5
H9A—C9—H9C	109.5	H24B—C24—H24C	109.5
H9B—C9—H9C	109.5	C26—C25—C22	112.89 (16)
C11—C10—C6	110.33 (17)	C26—C25—H25A	109.0
C11—C10—H10A	109.6	C22—C25—H25A	109.0
C6—C10—H10A	109.6	C26—C25—H25B	109.0
C11—C10—H10B	109.6	C22—C25—H25B	109.0
C6—C10—H10B	109.6	H25A—C25—H25B	107.8
H10A—C10—H10B	108.1	C27—C26—C25	110.62 (16)
C10—C11—C12	113.46 (17)	C27—C26—H26A	109.5
C10—C11—H11A	108.9	C25—C26—H26A	109.5
C12—C11—H11A	108.9	C27—C26—H26B	109.5
C10—C11—H11B	108.9	C25—C26—H26B	109.5
C12—C11—H11B	108.9	H26A—C26—H26B	108.1
H11A—C11—H11B	107.7	O3—C27—C26	121.62 (19)
O2—C12—C14	108.86 (16)	O3—C27—C28	121.16 (18)
O2—C12—C11	108.74 (17)	C26—C27—C28	117.20 (17)
C14—C12—C11	110.49 (18)	C27—C28—C30	109.20 (17)
O2—C12—C13	103.60 (15)	C27—C28—C29	105.32 (17)
C14—C12—C13	115.21 (17)	C30—C28—C29	107.38 (17)
C11—C12—C13	109.57 (16)	C27—C28—C21	111.30 (16)
C12—C13—C15	112.00 (16)	C30—C28—C21	108.59 (16)
C12—C13—C1	115.34 (16)	C29—C28—C21	114.86 (17)
C15—C13—C1	115.11 (16)	C28—C29—H29A	109.5
C12—C13—H13	104.2	C28—C29—H29B	109.5
C15—C13—H13	104.2	H29A—C29—H29B	109.5
C1—C13—H13	104.2	C28—C29—H29C	109.5
C12—C14—H14A	109.5	H29A—C29—H29C	109.5
C12—C14—H14B	109.5	H29B—C29—H29C	109.5
H14A—C14—H14B	109.5	C28—C30—H30A	109.5
C12—C14—H14C	109.5	C28—C30—H30B	109.5
H14A—C14—H14C	109.5	H30A—C30—H30B	109.5
H14B—C14—H14C	109.5	C28—C30—H30C	109.5
C16—C15—C13	112.40 (16)	H30A—C30—H30C	109.5
C16—C15—H15A	109.1	H30B—C30—H30C	109.5
C13—C15—H15A	109.1

C9—C1—C2—C3	69.8 (2)	C1—C13—C15—C16	99.7 (2)
C6—C1—C2—C3	−54.1 (2)	C13—C15—C16—C17	176.18 (17)
C13—C1—C2—C3	−168.58 (17)	C15—C16—C17—C18	−101.6 (2)
C1—C2—C3—C4	54.2 (2)	C15—C16—C17—C22	130.50 (18)
C2—C3—C4—O1	133.3 (2)	C22—C17—C18—C19	−12.3 (3)
C2—C3—C4—C5	−48.9 (3)	C16—C17—C18—C19	−140.2 (2)
O1—C4—C5—C8	−19.3 (3)	C22—C17—C18—C23	171.38 (17)
C3—C4—C5—C8	162.88 (19)	C16—C17—C18—C23	43.5 (2)
O1—C4—C5—C7	96.9 (2)	C23—C18—C19—C20	171.8 (2)
C3—C4—C5—C7	−81.0 (2)	C17—C18—C19—C20	−4.3 (3)
O1—C4—C5—C6	−139.1 (2)	C18—C19—C20—C21	−15.5 (3)
C3—C4—C5—C6	43.1 (2)	C19—C20—C21—C22	50.8 (2)
C2—C1—C6—C10	−175.45 (16)	C19—C20—C21—C28	−175.54 (17)
C9—C1—C6—C10	64.2 (2)	C20—C21—C22—C25	176.90 (16)
C13—C1—C6—C10	−59.6 (2)	C28—C21—C22—C25	45.9 (2)
C2—C1—C6—C5	51.8 (2)	C20—C21—C22—C24	54.7 (2)
C9—C1—C6—C5	−68.5 (2)	C28—C21—C22—C24	−76.3 (2)
C13—C1—C6—C5	167.74 (17)	C20—C21—C22—C17	−66.60 (19)
C4—C5—C6—C10	−177.08 (17)	C28—C21—C22—C17	162.38 (16)
C8—C5—C6—C10	63.8 (2)	C18—C17—C22—C25	163.45 (16)
C7—C5—C6—C10	−57.2 (2)	C16—C17—C22—C25	−68.9 (2)
C4—C5—C6—C1	−45.7 (2)	C18—C17—C22—C24	−76.0 (2)
C8—C5—C6—C1	−164.88 (18)	C16—C17—C22—C24	51.7 (2)
C7—C5—C6—C1	74.2 (2)	C18—C17—C22—C21	46.3 (2)
C1—C6—C10—C11	62.1 (2)	C16—C17—C22—C21	173.97 (15)
C5—C6—C10—C11	−162.95 (18)	C24—C22—C25—C26	67.7 (2)
C6—C10—C11—C12	−57.2 (2)	C21—C22—C25—C26	−55.6 (2)
C10—C11—C12—O2	163.03 (17)	C17—C22—C25—C26	−171.57 (16)
C10—C11—C12—C14	−77.5 (2)	C22—C25—C26—C27	59.3 (2)
C10—C11—C12—C13	50.4 (2)	C25—C26—C27—O3	129.9 (2)
O2—C12—C13—C15	58.4 (2)	C25—C26—C27—C28	−51.7 (2)
C14—C12—C13—C15	−60.4 (2)	O3—C27—C28—C30	−21.1 (3)
C11—C12—C13—C15	174.34 (16)	C26—C27—C28—C30	160.48 (18)
O2—C12—C13—C1	−167.31 (16)	O3—C27—C28—C29	94.0 (2)
C14—C12—C13—C1	73.9 (2)	C26—C27—C28—C29	−84.5 (2)
C11—C12—C13—C1	−51.4 (2)	O3—C27—C28—C21	−140.96 (19)
C2—C1—C13—C12	171.36 (16)	C26—C27—C28—C21	40.6 (2)
C9—C1—C13—C12	−69.2 (2)	C20—C21—C28—C27	−167.41 (17)
C6—C1—C13—C12	55.8 (2)	C22—C21—C28—C27	−38.2 (2)
C2—C1—C13—C15	−55.8 (2)	C20—C21—C28—C30	72.3 (2)
C9—C1—C13—C15	63.6 (2)	C22—C21—C28—C30	−158.42 (17)
C6—C1—C13—C15	−171.39 (16)	C20—C21—C28—C29	−47.9 (2)
C12—C13—C15—C16	−125.90 (18)	C22—C21—C28—C29	81.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.84 (1)	2.15 (1)	2.974 (2)	167 (3)

Symmetry code: (i) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₃₀H₄₈O₃
M_r	456.68
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	11.8841 (11), 14.8301 (13), 15.2755 (13)
V (Å³)	2692.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26171, 3469, 3033
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.098, 1.01
No. of reflections	3469
No. of parameters	310
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)	0.25, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
O2—H2···O3ⁱ	0.84 (1)	2.15 (1)	2.974 (2)	167 (3)

Symmetry code: (i) −x+2, y+1/2, −z+3/2.

Acknowledgements

This work was supported by the Directorate of Higher Education, Indonesia, the University of Padjadjaran (I-MHERE Project) and the University of Malaya (UMRG RG011/09BIO).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mayanti, T., Supratman, U., Mukhtar, M. R., Awang, K. & Ng, S. W. (2009). Acta Cryst. E65, o750. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tjokronegero, R., Mayanti, T., Supratman, U., Mukhtar, M. R. & Ng, S. W. (2009). Acta Cryst. E65, o1448. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar

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Volume 66| Part 7| July 2010| Page o1621

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

14-Hy­dr­oxy-8,14-secogammacera-7-ene-3,21-dione from the bark of Lansium domesticum Corr.

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

14-Hydroxy-8,14-secogammacera-7-ene-3,21-dione from the bark of Lansium domesticum Corr.