2-Hy­droxy-7-meth­oxy-9H-carbazole-3-carbaldehyde

Fun, H.-K.; Maneerat, W.; Laphookhieo, S.; Chantrapromma, S.

doi:10.1107/S1600536810033805

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2418-o2419

https://doi.org/10.1107/S1600536810033805

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2-Hydroxy-7-methoxy-9H-carbazole-3-carbaldehyde

Hoong-Kun Fun,^a ^*‡ Wisanu Maneerat,^b Surat Laphookhieo ^b and Suchada Chantrapromma ^c §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bNatural Products Research Laboratory, School of Science, Mae Fah Luang University, Tasud, Muang, Chiang Rai 57100, Thailand, and ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 20 August 2010; accepted 21 August 2010; online 28 August 2010)

The title compound, C₁₄H₁₁NO₃, was isolated from the roots of Clausena wallichii. The carbazole ring system is approximately planar (r.m.s. deviation = 0.039 Å) and the dihedral angle between the two benzene rings is 4.63 (7)°. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked into a zigzag network extending parallel to the ac plane by O—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For compounds isolated from plants of genera Rutaceae and their pharmacological activity, see: Ito et al. (1997 ); Kongkathip & Kongkathip (2009 ); Laphookhieo et al. (2009 ); Li et al. (1991 ); Maneerat & Laphookhieo (2010 ); Maneerat et al. (2010 ); Sripisut & Laphookhieo (2010 ); Tangyuenyongwatthana et al. (1992 ); Yenjai et al. 2000 ). For a related structure, see: Fun et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ).

Experimental

Crystal data

C₁₄H₁₁NO₃
M_r = 241.24
Orthorhombic, P n a 2₁
a = 12.4352 (4) Å
b = 17.6564 (5) Å
c = 5.0839 (1) Å
V = 1116.23 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.84 mm⁻¹
T = 100 K
0.23 × 0.19 × 0.10 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.831, T_max = 0.918
25207 measured reflections
2026 independent reflections
2018 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.097
S = 1.31
2026 reflections
170 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.63 e Å⁻³
Absolute structure: Flack (1983 ), 851 Friedel pairs
Flack parameter: 0.17 (19)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.81	1.96	2.6453 (17)	143
O1—H1O1⋯N1ⁱ	0.81	2.53	3.0457 (15)	123
N1—H1N1⋯O2ⁱⁱ	0.85 (2)	2.10 (2)	2.941 (2)	172 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-1]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810033805/ci5167sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033805/ci5167Isup2.hkl

checkCIF report

Comment top

Rutaceae plants are known to be rich sources of coumarins and carbazole alkaloids. Many of them have been isolated from several genera of Rutaceae especially from Clausena genus (Laphookhieo et al., 2009; Maneerat et al., 2010; Sripisut & Laphookhieo 2010; Kongkathip & Kongkathip 2009; Ito et al., 1997; Li et al., 1991; Tangyuenyongwatthana et al., 1992) and some of these compounds show interesting pharmacological activities (Maneerat & Laphookhieo 2010; Yenjai et al. 2000). Although Clausena wallichii is one of the Rutaceae plants, however phytochemical reports on the chemical constituents from this plant are rare. As part of our continuing study of chemical constituents and bioactive compounds from Thai medicinal plants, we report herein the crystal structure of the title compound, which was isolated from the roots of C. wallichii collected from Phrae province in the northern region of Thailand.

The non-hydrogen atoms of the title molecule (Fig. 1) are almost coplanar. The carbazole ring system (C1-C12/N1) is planar with an r.m.s. deviation of 0.039 Å [maximum deviation 0.072 (1) Å for atom C7]. The pyrrole ring makes dihedral angle of 1.66 (7) and 3.12 (8)°, respectively, with the C1–C4/C10–C11 and C5–C9/C12 benzene rings. The dihedral angle between the two benzene rings being 4.63 (7)°. The cabaldehyde and methoxy substituents at atoms C3 and C7, respectively, are coplanar with the benzene ring, as indicated by torsion angles C2–C3–C13–O2 = 0.0 (2)° and C14–O3–C7–C8 = 4.0 (2)°. An intramolecular O1—H1O1···O2 hydrogen bond (Table 1) generates an S(6) ring motif (Fig. 1 and Table 1) (Bernstein et al., 1995). The bond distances are within normal ranges (Allen et al., 1987) and comparable to a related structure (Fun et al., 2009).

The crystal packing of the title compound is stabilized by intermolecular O—H···N and N—H···O hydrogen bonds (Table 1) which link the molecules into a zigzag network extending parallel to the ac plane.

Related literature top

For compounds isolated from plants of genera Rutaceae and their pharmacological activity, see: Ito et al. (1997); Kongkathip & Kongkathip (2009); Laphookhieo et al. (2009); Li et al. (1991); Maneerat & Laphookhieo (2010); Maneerat et al. (2010); Sripisut & Laphookhieo (2010); Tangyuenyongwatthana et al. (1992); Yenjai et al. 2000). For a related structure, see: Fun et al. (2009). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental top

The roots of C. wallichii (1.02 Kg) were successively extracted with CH₂Cl₂ over the period of 3 days each at room temperature to provide the crude CH₂Cl₂ extract which subjected to quick column chromatography (QCC) over silica gel eluted with a gradient of hexane-EtOAc (100% hexane to 100% EtOAc) to provide nine fractions (A-I). Fraction G (3.12 g) was further separated by QCC with a gradient of 10% EtOAc-hexane to 100% EtOAc to give seven subfractions (G1-G7). Subfraction G4 (118.9 mg) was subjected to repeated column chromatography using 30% EtOAc-hexane to yield the yellow solid of the title compound (12.8 mg). Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from CH₂Cl₂/acetone (1:1 v/v) by the slow evaporation of the solvent at room temperature after several days; m.p. 496.7-498.8 K (decomposition).

Structure description top

For compounds isolated from plants of genera Rutaceae and their pharmacological activity, see: Ito et al. (1997); Kongkathip & Kongkathip (2009); Laphookhieo et al. (2009); Li et al. (1991); Maneerat & Laphookhieo (2010); Maneerat et al. (2010); Sripisut & Laphookhieo (2010); Tangyuenyongwatthana et al. (1992); Yenjai et al. 2000). For a related structure, see: Fun et al. (2009). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The O—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. Part of the crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

2-Hydroxy-7-methoxy-9H-carbazole-3-carbaldehyde top

Crystal data top

C₁₄H₁₁NO₃	D_x = 1.435 Mg m⁻³
M_r = 241.24	Melting point = 496.7–498.8 K
Orthorhombic, Pna2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2n	Cell parameters from 2026 reflections
a = 12.4352 (4) Å	θ = 4.4–69.9°
b = 17.6564 (5) Å	µ = 0.84 mm⁻¹
c = 5.0839 (1) Å	T = 100 K
V = 1116.23 (5) Å³	Plate, yellow
Z = 4	0.23 × 0.19 × 0.10 mm
F(000) = 504

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	2026 independent reflections
Radiation source: sealed tube	2018 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 69.9°, θ_min = 4.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.831, T_max = 0.918	k = −21→21
25207 measured reflections	l = −5→6

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0656P)² + 0.054P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.097	(Δ/σ)_max = 0.001
S = 1.31	Δρ_max = 0.64 e Å⁻³
2026 reflections	Δρ_min = −0.63 e Å⁻³
170 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.053 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 851 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.17 (19)

Crystal data top

C₁₄H₁₁NO₃	V = 1116.23 (5) Å³
M_r = 241.24	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 12.4352 (4) Å	µ = 0.84 mm⁻¹
b = 17.6564 (5) Å	T = 100 K
c = 5.0839 (1) Å	0.23 × 0.19 × 0.10 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	2026 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2018 reflections with I > 2σ(I)
T_min = 0.831, T_max = 0.918	R_int = 0.027
25207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	Δρ_max = 0.64 e Å⁻³
S = 1.31	Δρ_min = −0.63 e Å⁻³
2026 reflections	Absolute structure: Flack (1983), 851 Friedel pairs
170 parameters	Absolute structure parameter: 0.17 (19)
1 restraint

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.59667 (8)	0.17861 (6)	0.4400 (2)	0.0264 (3)
H1O1	0.6537	0.1796	0.5149	0.056 (7)*
O2	0.72058 (8)	0.20104 (6)	0.8557 (3)	0.0294 (3)
O3	0.12071 (9)	0.59553 (6)	0.5822 (3)	0.0325 (3)
N1	0.32559 (9)	0.37021 (7)	0.3111 (3)	0.0203 (3)
H1N1	0.2898 (14)	0.3514 (10)	0.185 (5)	0.029 (5)*
C1	0.46098 (10)	0.26763 (8)	0.3568 (3)	0.0213 (3)
H1A	0.4366	0.2391	0.2150	0.026*
C2	0.54764 (10)	0.24453 (8)	0.5070 (3)	0.0212 (3)
C3	0.58509 (11)	0.28796 (8)	0.7249 (3)	0.0220 (3)
C4	0.53291 (10)	0.35607 (8)	0.7921 (3)	0.0208 (3)
H4A	0.5569	0.3847	0.9339	0.025*
C5	0.36091 (11)	0.50464 (7)	0.8333 (3)	0.0226 (3)
H5A	0.4092	0.5117	0.9708	0.027*
C6	0.27613 (11)	0.55440 (8)	0.7967 (3)	0.0241 (3)
H6A	0.2680	0.5955	0.9094	0.029*
C7	0.20217 (11)	0.54348 (8)	0.5906 (3)	0.0238 (3)
C8	0.21259 (10)	0.48413 (7)	0.4134 (3)	0.0222 (4)
H8A	0.1644	0.4774	0.2756	0.027*
C9	0.29943 (10)	0.43496 (7)	0.4528 (3)	0.0195 (3)
C10	0.41167 (10)	0.33567 (7)	0.4277 (3)	0.0196 (3)
C11	0.44591 (10)	0.37986 (8)	0.6456 (3)	0.0194 (3)
C12	0.37263 (11)	0.44372 (8)	0.6603 (3)	0.0203 (3)
C13	0.67188 (10)	0.26163 (8)	0.8877 (3)	0.0244 (3)
H13A	0.6930	0.2923	1.0273	0.029*
C14	0.03861 (12)	0.58496 (9)	0.3899 (4)	0.0354 (4)
H14A	−0.0179	0.6211	0.4184	0.053*
H14B	0.0101	0.5346	0.4043	0.053*
H14C	0.0684	0.5921	0.2174	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0261 (5)	0.0281 (5)	0.0251 (6)	0.0080 (4)	−0.0009 (4)	−0.0024 (5)
O2	0.0282 (5)	0.0358 (6)	0.0241 (7)	0.0098 (4)	−0.0016 (4)	0.0011 (5)
O3	0.0345 (6)	0.0291 (6)	0.0340 (7)	0.0104 (4)	−0.0052 (5)	−0.0053 (5)
N1	0.0207 (6)	0.0215 (6)	0.0187 (6)	0.0000 (4)	−0.0025 (5)	−0.0007 (5)
C1	0.0224 (6)	0.0225 (7)	0.0188 (8)	−0.0013 (5)	0.0010 (6)	−0.0003 (5)
C2	0.0202 (6)	0.0226 (6)	0.0209 (8)	0.0007 (5)	0.0047 (5)	0.0017 (6)
C3	0.0206 (7)	0.0242 (7)	0.0212 (8)	−0.0011 (5)	0.0019 (6)	0.0032 (6)
C4	0.0207 (6)	0.0234 (7)	0.0183 (8)	−0.0035 (5)	0.0000 (5)	0.0005 (6)
C5	0.0257 (7)	0.0221 (7)	0.0199 (7)	−0.0044 (5)	−0.0007 (6)	0.0000 (6)
C6	0.0303 (7)	0.0204 (6)	0.0217 (8)	−0.0017 (5)	0.0022 (6)	−0.0028 (6)
C7	0.0258 (7)	0.0210 (7)	0.0246 (8)	0.0016 (5)	0.0025 (6)	0.0029 (6)
C8	0.0226 (7)	0.0224 (7)	0.0216 (9)	−0.0004 (5)	−0.0014 (5)	0.0023 (6)
C9	0.0201 (6)	0.0195 (6)	0.0191 (8)	−0.0028 (5)	0.0020 (5)	0.0005 (6)
C10	0.0179 (6)	0.0217 (7)	0.0193 (8)	−0.0026 (4)	0.0014 (5)	0.0020 (6)
C11	0.0211 (6)	0.0191 (6)	0.0180 (8)	−0.0036 (5)	0.0023 (5)	0.0016 (5)
C12	0.0214 (7)	0.0188 (6)	0.0206 (8)	−0.0030 (5)	0.0015 (5)	0.0031 (6)
C13	0.0238 (6)	0.0297 (7)	0.0198 (9)	−0.0003 (5)	−0.0001 (6)	0.0025 (6)
C14	0.0353 (8)	0.0360 (9)	0.0348 (11)	0.0131 (6)	−0.0077 (7)	−0.0022 (8)

Geometric parameters (Å, º) top

O1—C2	1.3574 (17)	C5—C6	1.3850 (19)
O1—H1O1	0.81	C5—C12	1.397 (2)
O2—C13	1.2401 (17)	C5—H5A	0.93
O3—C7	1.3685 (16)	C6—C7	1.407 (2)
O3—C14	1.426 (2)	C6—H6A	0.93
N1—C10	1.3671 (18)	C7—C8	1.388 (2)
N1—C9	1.3899 (18)	C8—C9	1.4000 (17)
N1—H1N1	0.85 (2)	C8—H8A	0.93
C1—C2	1.382 (2)	C9—C12	1.402 (2)
C1—C10	1.3960 (18)	C10—C11	1.420 (2)
C1—H1A	0.93	C11—C12	1.4517 (18)
C2—C3	1.425 (2)	C13—H13A	0.93
C3—C4	1.4086 (19)	C14—H14A	0.96
C3—C13	1.438 (2)	C14—H14B	0.96
C4—C11	1.379 (2)	C14—H14C	0.96
C4—H4A	0.93

C2—O1—H1O1	104.9	C8—C7—C6	121.71 (13)
C7—O3—C14	117.62 (13)	C7—C8—C9	116.58 (13)
C10—N1—C9	109.00 (13)	C7—C8—H8A	121.7
C10—N1—H1N1	124.3 (12)	C9—C8—H8A	121.7
C9—N1—H1N1	126.2 (12)	N1—C9—C8	128.06 (14)
C2—C1—C10	116.99 (14)	N1—C9—C12	109.20 (12)
C2—C1—H1A	121.5	C8—C9—C12	122.69 (13)
C10—C1—H1A	121.5	N1—C10—C1	128.02 (14)
O1—C2—C1	117.68 (14)	N1—C10—C11	109.13 (12)
O1—C2—C3	120.64 (13)	C1—C10—C11	122.84 (13)
C1—C2—C3	121.67 (13)	C4—C11—C10	119.28 (13)
C4—C3—C2	119.83 (13)	C4—C11—C12	134.53 (14)
C4—C3—C13	118.83 (14)	C10—C11—C12	106.18 (12)
C2—C3—C13	121.25 (13)	C5—C12—C9	119.41 (12)
C11—C4—C3	119.36 (14)	C5—C12—C11	134.10 (14)
C11—C4—H4A	120.3	C9—C12—C11	106.45 (12)
C3—C4—H4A	120.3	O2—C13—C3	124.75 (14)
C6—C5—C12	118.88 (14)	O2—C13—H13A	117.6
C6—C5—H5A	120.6	C3—C13—H13A	117.6
C12—C5—H5A	120.6	O3—C14—H14A	109.5
C5—C6—C7	120.71 (14)	O3—C14—H14B	109.5
C5—C6—H6A	119.6	H14A—C14—H14B	109.5
C7—C6—H6A	119.6	O3—C14—H14C	109.5
O3—C7—C8	123.77 (14)	H14A—C14—H14C	109.5
O3—C7—C6	114.52 (14)	H14B—C14—H14C	109.5

C10—C1—C2—O1	−179.79 (13)	C2—C1—C10—N1	179.92 (13)
C10—C1—C2—C3	0.13 (19)	C2—C1—C10—C11	−1.0 (2)
O1—C2—C3—C4	−179.74 (12)	C3—C4—C11—C10	−0.9 (2)
C1—C2—C3—C4	0.3 (2)	C3—C4—C11—C12	177.97 (14)
O1—C2—C3—C13	−3.2 (2)	N1—C10—C11—C4	−179.38 (12)
C1—C2—C3—C13	176.88 (12)	C1—C10—C11—C4	1.4 (2)
C2—C3—C4—C11	0.0 (2)	N1—C10—C11—C12	1.49 (15)
C13—C3—C4—C11	−176.59 (13)	C1—C10—C11—C12	−177.74 (12)
C12—C5—C6—C7	0.7 (2)	C6—C5—C12—C9	0.8 (2)
C14—O3—C7—C8	4.0 (2)	C6—C5—C12—C11	−176.30 (14)
C14—O3—C7—C6	−175.73 (14)	N1—C9—C12—C5	−178.86 (12)
C5—C6—C7—O3	178.13 (13)	C8—C9—C12—C5	−1.4 (2)
C5—C6—C7—C8	−1.7 (2)	N1—C9—C12—C11	−1.06 (15)
O3—C7—C8—C9	−178.74 (13)	C8—C9—C12—C11	176.40 (12)
C6—C7—C8—C9	1.0 (2)	C4—C11—C12—C5	−1.9 (3)
C10—N1—C9—C8	−175.26 (13)	C10—C11—C12—C5	177.08 (15)
C10—N1—C9—C12	2.04 (15)	C4—C11—C12—C9	−179.18 (15)
C7—C8—C9—N1	177.45 (14)	C10—C11—C12—C9	−0.25 (15)
C7—C8—C9—C12	0.49 (19)	C4—C3—C13—O2	176.58 (13)
C9—N1—C10—C1	176.99 (13)	C2—C3—C13—O2	0.0 (2)
C9—N1—C10—C11	−2.19 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.81	1.96	2.6453 (17)	143
O1—H1O1···N1ⁱ	0.81	2.53	3.0457 (15)	123
N1—H1N1···O2ⁱⁱ	0.85 (2)	2.10 (2)	2.941 (2)	172 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁NO₃
M_r	241.24
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	12.4352 (4), 17.6564 (5), 5.0839 (1)
V (Å³)	1116.23 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.23 × 0.19 × 0.10

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.831, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	25207, 2026, 2018
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.097, 1.31
No. of reflections	2026
No. of parameters	170
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)	0.64, −0.63
Absolute structure	Flack (1983), 851 Friedel pairs
Absolute structure parameter	0.17 (19)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.81	1.96	2.6453 (17)	143
O1—H1O1···N1ⁱ	0.81	2.53	3.0457 (15)	123
N1—H1N1···O2ⁱⁱ	0.85 (2)	2.10 (2)	2.941 (2)	172 (2)

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

SL and WM are grateful to the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0006/2552) and Mae Fah Luang University for financial support. SC thanks Prince of Songkla University for generous support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

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