3-(7-Meth­oxy-β-carbolin-1-yl)propionic acid monohydrate

Dai, D.-M.; Zhong, J.-L.; An, H.-M.; Zou, J.-W.

doi:10.1107/S160053681101350X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1167

doi:10.1107/S160053681101350X

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3-(7-Methoxy-β-carbolin-1-yl)propionic acid monohydrate

Dong-Mei Dai,^a ^* Jia-Liang Zhong,^b Hui-Mei An ^c and Jian-Wei Zou ^a

^aKey Laboratory for Molecular Design and Nutrition Engineering, Ningbo Institute of Technology, Zhejiang University, 1st Qianhu Nan Road, Ningbo 315100, People's Republic of China, ^bShanghai Institute of Pharmaceutical Industry, 1320 Beijing Road (West), Shanghai 200040, People's Republic of China, and ^cBeijing Huilongguan Hospital, No.1 Nandian Huilongguan, Changping District, Beijing 100096, People's Republic of China
^*Correspondence e-mail: happyddm@126.com

(Received 18 March 2011; accepted 11 April 2011; online 16 April 2011)

In the title compound, C₁₅H₁₄N₂O₃·H₂O [systematic name: 3-(7-methoxy-9H-pyrido[3,4-b]indol-1-yl)propanoic acid monohydrate], the fused rings make dhedral angles of 0.4 (1), 1.1 (2) and 1.4 (2)°. In the crystal, the water molecule is involved in the formation of three independent hydrogen-bonded chains via O—H⋯O and N—H⋯O hydrogen bonds, while the carboxy group forms an intermolecular O—H⋯N hydrogen bond.

Related literature

For the isolation of the title compound, see: Kardono et al. (1991 ). For the preparation, see: Kardono et al. (1991). For its pharmacological activity, see: Kuo et al. (2003 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₃·H₂O
M_r = 288.30
Monoclinic, P 2₁ /n
a = 4.5114 (1) Å
b = 10.8637 (2) Å
c = 28.0865 (3) Å
β = 92.414 (1)°
V = 1375.31 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 296 K
0.12 × 0.10 × 0.05 mm

Data collection

Bruker APEXII diffractometer
9119 measured reflections
2366 independent reflections
2048 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.116
S = 1.05
2366 reflections
201 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13A⋯OWⁱ	0.86	1.86	2.7224 (18)	180
O5′—H5′A⋯N2ⁱⁱ	0.82	1.79	2.5965 (18)	169
OW—HWA⋯O5′ⁱⁱⁱ	0.85 (3)	1.92 (3)	2.7514 (19)	169 (2)
OW—HWB⋯O4′^iv	0.87 (3)	1.89 (3)	2.764 (2)	175 (2)
Symmetry codes: (i) x-1, y, z; (ii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101350X/mw2003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101350X/mw2003Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was isolated from the roots of Eurycoma longifolia. It is prepared according to the procedure of Kardono et al. (Kardono et al., 1991) and recrystallized from methanol.

Bond lengths and angles are in agreement with reported literature values (Allen et al., 1987). The rings (A, B and C) are each essentially planar with r.m.s deviations of 0.0018 (5) Å, 0.0027 (8)Å and 0.0052 (16) Å, respectively. The dihedral angles between the rings are A/B =1.1 (2)°, A/C = 0.4 (1)° and B/C=1.4 (2)°. The lattice water molecule is involved in formation of three independent hydrogen-bonded chains via O—H···O and N—H···O hydrogen bonds while the carboxy group forms an intermolecular O—H···N hydrogen bond (Fig.2 and Table 1). The lattice water molecules could be considered to be a hydrogen-bond bridge which provide further stability to the crystal lattice.

Related literature top

For the isolation of the title compound, see: Kardono et al. (1991). For general background, see: Kardono et al. (1991); Kuo et al. (2003). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to the procedure of Kardono et al., 1991.Crystals suitable for data collection were obtained by slow evaporation from methanol solution at 283 K over a period of two weeks.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The packing of the title compound,viewed down the a axis. The dashed line indicates the hydrogen bond.

3-(7-methoxy-9H-pyrido[3,4-b]indol-1-yl)propanoic acid monohydrate top

Crystal data top

C₁₅H₁₄N₂O₃·H₂O	F(000) = 608
M_r = 288.30	D_x = 1.392 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 3368 reflections
a = 4.5114 (1) Å	θ = 3.2–67.6°
b = 10.8637 (2) Å	µ = 0.85 mm⁻¹
c = 28.0865 (3) Å	T = 296 K
β = 92.414 (1)°	Prism, colourless
V = 1375.31 (4) Å³	0.12 × 0.10 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2048 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 67.6°, θ_min = 3.2°
Detector resolution: 0 pixels mm^-1	h = −4→5
ϕ and ω scans	k = −12→12
9119 measured reflections	l = −33→33
2366 independent 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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0672P)² + 0.3134P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.006
2366 reflections	Δρ_max = 0.49 e Å⁻³
201 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (3)

Crystal data top

C₁₅H₁₄N₂O₃·H₂O	V = 1375.31 (4) Å³
M_r = 288.30	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 4.5114 (1) Å	µ = 0.85 mm⁻¹
b = 10.8637 (2) Å	T = 296 K
c = 28.0865 (3) Å	0.12 × 0.10 × 0.05 mm
β = 92.414 (1)°

Data collection top

Bruker APEXII diffractometer	2048 reflections with I > 2σ(I)
9119 measured reflections	R_int = 0.022
2366 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.49 e Å⁻³
2366 reflections	Δρ_min = −0.17 e Å⁻³
201 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.0343 (3)	0.45008 (14)	0.16867 (5)	0.0351 (3)
N2	0.0495 (3)	0.32718 (11)	0.16361 (5)	0.0402 (3)
C3	0.2158 (4)	0.27148 (15)	0.13080 (6)	0.0458 (4)
H3A	0.2177	0.1860	0.1291	0.055*
C4	0.3807 (4)	0.33780 (15)	0.10014 (6)	0.0438 (4)
H4A	0.4925	0.2985	0.0776	0.053*
C5	0.7128 (4)	0.57535 (16)	0.04262 (6)	0.0443 (4)
H5A	0.7804	0.5050	0.0276	0.053*
C6	0.8037 (4)	0.68936 (17)	0.02872 (6)	0.0487 (4)
H6A	0.9324	0.6962	0.0039	0.058*
C7	0.7055 (4)	0.79694 (16)	0.05145 (6)	0.0460 (4)
C8	0.5138 (4)	0.79159 (15)	0.08833 (6)	0.0427 (4)
H8A	0.4502	0.8624	0.1035	0.051*
C9	0.4200 (3)	0.67511 (14)	0.10178 (5)	0.0374 (4)
C10	0.5163 (3)	0.56590 (14)	0.07978 (5)	0.0381 (4)
C11	0.3771 (3)	0.46622 (14)	0.10355 (5)	0.0370 (3)
C12	0.2008 (3)	0.52071 (14)	0.13862 (5)	0.0350 (3)
N13	0.2299 (3)	0.64599 (12)	0.13699 (4)	0.0381 (3)
H13A	0.1437	0.6978	0.1550	0.046*
O14	0.8192 (3)	0.90335 (12)	0.03401 (5)	0.0602 (4)
C15	0.7305 (6)	1.01607 (19)	0.05520 (8)	0.0734 (7)
H15A	0.8250	1.0837	0.0399	0.110*
H15B	0.7877	1.0156	0.0885	0.110*
H15C	0.5191	1.0248	0.0514	0.110*
C1'	−0.1536 (3)	0.50276 (13)	0.20627 (5)	0.0364 (4)
H1'A	−0.3104	0.4449	0.2129	0.044*
H1'B	−0.2458	0.5780	0.1944	0.044*
C2'	0.0251 (4)	0.53087 (15)	0.25274 (6)	0.0437 (4)
H2'A	0.0966	0.4545	0.2670	0.052*
H2'B	0.1957	0.5811	0.2458	0.052*
C3'	−0.1657 (4)	0.59823 (14)	0.28756 (5)	0.0416 (4)
O4'	−0.2512 (4)	0.54636 (12)	0.32330 (4)	0.0655 (4)
O5'	−0.2315 (4)	0.70783 (11)	0.27682 (5)	0.0618 (4)
H5'A	−0.3268	0.7384	0.2981	0.25 (3)*
OW	0.9592 (4)	0.81052 (13)	0.19395 (6)	0.0690 (5)
HWA	0.894 (5)	0.789 (2)	0.2205 (10)	0.081 (8)*
HWB	0.882 (5)	0.883 (3)	0.1889 (9)	0.076 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0370 (8)	0.0361 (8)	0.0322 (7)	−0.0001 (6)	0.0022 (6)	−0.0003 (6)
N2	0.0474 (8)	0.0356 (7)	0.0381 (7)	0.0008 (5)	0.0062 (6)	−0.0012 (5)
C3	0.0572 (10)	0.0358 (8)	0.0450 (9)	0.0031 (7)	0.0082 (7)	−0.0047 (6)
C4	0.0489 (9)	0.0433 (9)	0.0397 (8)	0.0070 (7)	0.0089 (7)	−0.0061 (6)
C5	0.0431 (9)	0.0531 (10)	0.0374 (8)	0.0014 (7)	0.0097 (7)	−0.0048 (7)
C6	0.0482 (10)	0.0627 (11)	0.0363 (8)	−0.0041 (8)	0.0146 (7)	0.0008 (7)
C7	0.0487 (9)	0.0521 (10)	0.0375 (8)	−0.0068 (7)	0.0064 (7)	0.0072 (7)
C8	0.0483 (9)	0.0419 (9)	0.0383 (8)	−0.0002 (7)	0.0084 (7)	0.0012 (6)
C9	0.0384 (8)	0.0422 (8)	0.0318 (7)	0.0006 (6)	0.0049 (6)	0.0006 (6)
C10	0.0376 (8)	0.0443 (9)	0.0326 (7)	0.0012 (6)	0.0039 (6)	−0.0012 (6)
C11	0.0371 (8)	0.0411 (8)	0.0330 (7)	0.0028 (6)	0.0029 (6)	−0.0026 (6)
C12	0.0362 (8)	0.0372 (8)	0.0316 (7)	0.0019 (6)	0.0033 (6)	−0.0009 (6)
N13	0.0440 (7)	0.0350 (7)	0.0362 (6)	0.0021 (5)	0.0120 (5)	−0.0008 (5)
O14	0.0749 (9)	0.0543 (8)	0.0530 (7)	−0.0113 (6)	0.0232 (6)	0.0087 (6)
C15	0.1093 (18)	0.0520 (12)	0.0610 (12)	−0.0196 (11)	0.0274 (12)	0.0019 (9)
C1'	0.0378 (8)	0.0352 (8)	0.0367 (8)	−0.0002 (6)	0.0081 (6)	0.0004 (6)
C2'	0.0472 (9)	0.0451 (9)	0.0389 (8)	0.0062 (7)	0.0038 (7)	−0.0023 (7)
C3'	0.0501 (9)	0.0387 (8)	0.0365 (8)	−0.0028 (6)	0.0061 (7)	−0.0041 (6)
O4'	0.1062 (11)	0.0451 (7)	0.0477 (7)	−0.0034 (7)	0.0302 (7)	−0.0001 (5)
O5'	0.0916 (10)	0.0433 (7)	0.0528 (8)	0.0155 (6)	0.0297 (7)	0.0040 (5)
OW	0.1082 (13)	0.0425 (7)	0.0594 (9)	0.0149 (7)	0.0382 (8)	0.0023 (6)

Geometric parameters (Å, º) top

C1—N2	1.3447 (19)	C10—C11	1.431 (2)
C1—C12	1.385 (2)	C11—C12	1.421 (2)
C1—C1'	1.4955 (19)	C12—N13	1.3683 (19)
N2—C3	1.355 (2)	N13—H13A	0.8600
C3—C4	1.367 (2)	O14—C15	1.426 (2)
C3—H3A	0.9300	C15—H15A	0.9600
C4—C11	1.399 (2)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.367 (2)	C1'—C2'	1.535 (2)
C5—C10	1.401 (2)	C1'—H1'A	0.9700
C5—H5A	0.9300	C1'—H1'B	0.9700
C6—C7	1.412 (2)	C2'—C3'	1.518 (2)
C6—H6A	0.9300	C2'—H2'A	0.9700
C7—O14	1.364 (2)	C2'—H2'B	0.9700
C7—C8	1.378 (2)	C3'—O4'	1.228 (2)
C8—C9	1.392 (2)	C3'—O5'	1.261 (2)
C8—H8A	0.9300	O5'—H5'A	0.8200
C9—N13	1.3728 (19)	OW—HWA	0.85 (3)
C9—C10	1.414 (2)	OW—HWB	0.87 (3)

N2—C1—C12	117.01 (13)	N13—C12—C1	128.81 (13)
N2—C1—C1'	119.18 (13)	N13—C12—C11	109.50 (13)
C12—C1—C1'	123.80 (13)	C1—C12—C11	121.69 (14)
C1—N2—C3	123.20 (13)	C12—N13—C9	108.49 (12)
N2—C3—C4	121.64 (15)	C12—N13—H13A	125.8
N2—C3—H3A	119.2	C9—N13—H13A	125.8
C4—C3—H3A	119.2	C7—O14—C15	117.49 (14)
C3—C4—C11	118.33 (14)	O14—C15—H15A	109.5
C3—C4—H4A	120.8	O14—C15—H15B	109.5
C11—C4—H4A	120.8	H15A—C15—H15B	109.5
C6—C5—C10	119.07 (15)	O14—C15—H15C	109.5
C6—C5—H5A	120.5	H15A—C15—H15C	109.5
C10—C5—H5A	120.5	H15B—C15—H15C	109.5
C5—C6—C7	121.16 (15)	C1—C1'—C2'	112.56 (12)
C5—C6—H6A	119.4	C1—C1'—H1'A	109.1
C7—C6—H6A	119.4	C2'—C1'—H1'A	109.1
O14—C7—C8	124.26 (16)	C1—C1'—H1'B	109.1
O14—C7—C6	114.16 (15)	C2'—C1'—H1'B	109.1
C8—C7—C6	121.58 (15)	H1'A—C1'—H1'B	107.8
C7—C8—C9	116.74 (15)	C3'—C2'—C1'	110.62 (13)
C7—C8—H8A	121.6	C3'—C2'—H2'A	109.5
C9—C8—H8A	121.6	C1'—C2'—H2'A	109.5
N13—C9—C8	127.69 (14)	C3'—C2'—H2'B	109.5
N13—C9—C10	109.52 (13)	C1'—C2'—H2'B	109.5
C8—C9—C10	122.79 (14)	H2'A—C2'—H2'B	108.1
C5—C10—C9	118.65 (14)	O4'—C3'—O5'	123.37 (15)
C5—C10—C11	134.97 (15)	O4'—C3'—C2'	120.80 (15)
C9—C10—C11	106.38 (13)	O5'—C3'—C2'	115.82 (14)
C4—C11—C12	118.13 (14)	C3'—O5'—H5'A	109.5
C4—C11—C10	135.75 (14)	HWA—OW—HWB	104 (2)
C12—C11—C10	106.11 (13)

C12—C1—N2—C3	−0.5 (2)	C5—C10—C11—C12	−179.98 (18)
C1'—C1—N2—C3	−179.45 (15)	C9—C10—C11—C12	0.48 (17)
C1—N2—C3—C4	−0.2 (3)	N2—C1—C12—N13	−178.44 (14)
N2—C3—C4—C11	0.6 (3)	C1'—C1—C12—N13	0.4 (2)
C10—C5—C6—C7	0.6 (3)	N2—C1—C12—C11	0.8 (2)
C5—C6—C7—O14	179.06 (15)	C1'—C1—C12—C11	179.69 (14)
C5—C6—C7—C8	−0.3 (3)	C4—C11—C12—N13	178.96 (13)
O14—C7—C8—C9	−179.74 (15)	C10—C11—C12—N13	−0.36 (17)
C6—C7—C8—C9	−0.5 (3)	C4—C11—C12—C1	−0.4 (2)
C7—C8—C9—N13	−179.63 (16)	C10—C11—C12—C1	−179.75 (14)
C7—C8—C9—C10	0.9 (2)	C1—C12—N13—C9	179.43 (15)
C6—C5—C10—C9	−0.3 (2)	C11—C12—N13—C9	0.09 (17)
C6—C5—C10—C11	−179.79 (17)	C8—C9—N13—C12	−179.34 (16)
N13—C9—C10—C5	179.93 (14)	C10—C9—N13—C12	0.22 (17)
C8—C9—C10—C5	−0.5 (2)	C8—C7—O14—C15	−0.7 (3)
N13—C9—C10—C11	−0.44 (17)	C6—C7—O14—C15	−179.95 (18)
C8—C9—C10—C11	179.14 (15)	N2—C1—C1'—C2'	95.18 (16)
C3—C4—C11—C12	−0.3 (2)	C12—C1—C1'—C2'	−83.68 (18)
C3—C4—C11—C10	178.79 (18)	C1—C1'—C2'—C3'	173.08 (13)
C5—C10—C11—C4	0.9 (3)	C1'—C2'—C3'—O4'	108.25 (18)
C9—C10—C11—C4	−178.66 (18)	C1'—C2'—C3'—O5'	−70.68 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···OWⁱ	0.86	1.86	2.7224 (18)	180
O5′—H5′A···N2ⁱⁱ	0.82	1.79	2.5965 (18)	169
OW—HWA···O5′ⁱⁱⁱ	0.85 (3)	1.92 (3)	2.7514 (19)	169 (2)
OW—HWB···O4′^iv	0.87 (3)	1.89 (3)	2.764 (2)	175 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x−1/2, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₃·H₂O
M_r	288.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	4.5114 (1), 10.8637 (2), 28.0865 (3)
β (°)	92.414 (1)
V (Å³)	1375.31 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.12 × 0.10 × 0.05

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9119, 2366, 2048
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.116, 1.05
No. of reflections	2366
No. of parameters	201
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.17

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···OWⁱ	0.86	1.86	2.7224 (18)	180
O5'—H5'A···N2ⁱⁱ	0.82	1.79	2.5965 (18)	169
OW—HWA···O5'ⁱⁱⁱ	0.85 (3)	1.92 (3)	2.7514 (19)	169 (2)
OW—HWB···O4'^iv	0.87 (3)	1.89 (3)	2.764 (2)	175 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x−1/2, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) −x+1/2, y+1/2, −z+1/2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kardono, L. B. S., Angerhofer, C. K., Tsauri, S., Padmawinata, K., Pezzuto, J. M. & Kinghorn, A. D. (1991). J. Nat. Prod. 54, 1360–1367. CrossRef PubMed CAS Web of Science Google Scholar
Kuo, P. C., Shi, L. S., Damu, A. G., Su, C. R., Huang, C. H., Ke, C. H., Wu, J. B., Lin, A. J., Bastow, K. F., Lee, K. H. & Wu, T. S. (2003). J. Nat. Prod. 66, 1324–1327. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page o1167

doi:10.1107/S160053681101350X

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