Glycozolidal

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

doi:10.1107/S1600536811024160

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1811-o1812

doi:10.1107/S1600536811024160

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Glycozolidal

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 17 June 2011; accepted 20 June 2011; online 25 June 2011)

The title compound known as glycozolidal (systematic name: 2,7-dimethoxy-9H-carbazole-3-carbaldehyde), C₁₅H₁₃NO₃, is a naturally occurring carbazole, which was isolated from the roots of Clausena lansium. The carbazole ring system is essentially planar, with an r.m.s. deviation of 0.0093 (1) Å. In the crystal, intermolecular N—H⋯O hydrogen bonds connect the molecules into a chain along the c axis. C—H⋯O, C—H⋯π and π–π interactions, with centroid–centroid distances of 3.5924 (6), 3.6576 (6) and 3.8613 (6) Å, are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to carbazole alkaloids and their activities, see: 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 ); Thongthoom et al. (2010 ); Yenjai et al. (2000 ). For related structures, see: Fun et al. (2007 , 2009 , 2010 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₅H₁₃NO₃
M_r = 255.26
Monoclinic, C 2/c
a = 20.5756 (4) Å
b = 8.1298 (1) Å
c = 14.0411 (3) Å
β = 98.871 (1)°
V = 2320.64 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.53 × 0.42 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.947, T_max = 0.984
13003 measured reflections
3381 independent reflections
3032 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.115
S = 1.04
3381 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C4/C11/C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3ⁱ	0.890 (17)	2.106 (17)	2.9758 (11)	165.2 (15)
C15—H15C⋯O2ⁱⁱ	0.98	2.44	3.3888 (14)	162
C15—H15A⋯Cg2ⁱⁱⁱ	0.98	2.91	3.6613 (12)	134
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: 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: 10.1107/S1600536811024160/is2736sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024160/is2736Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024160/is2736Isup3.cml

checkCIF report

Comment top

Carbazole alkaloids are major compounds found in Rutaceae plants, especially in Clausena genus (Laphookhieo et al., 2009; Li et al., 1991; Maneerat et al., 2010; Sripisut & Laphookhieo, 2010; Tangyuenyongwatthana et al., 1992) which showed diverse pharmacological activities such as anti-cancer, anti-malaria, anti-TB and anti-HIV (Kongkathip & Kongkathip, 2009; Yenjai et al., 2000; Thongthoom et al., 2010) properties. During the course of our on-going research on chemical constituents and bioactive compounds from Clausena plants (Maneerat et al., 2010; Maneerat & Laphookhieo, 2010; Sripisut & Laphookhieo, 2010), the title compound (I) which was known as glycozolidal (Li et al., 1991) was isolated from the roots of C. lansium which was collected from Nan province in the northern part of Thailand. Herein the isolation and crystal structure of (I) was reported.

In the structure of (I), C₁₅H₁₃NO₃ (Fig. 1), the carbazole ring system (C1–C12/N1) is essentially planar with an r.m.s. deviation of 0.0093 (1) Å. The aldehyde substituent is planarly attached to the benzene ring which can be indicated by the torsion angle C4–C3–C14–O2 = -3.35 (16)°. whereas the two methoxy groups are slightly deviated from their attached benzene rings with the torsion angles C13–O1–C2–C1 = -6.03 (14)° and C15–O3–C6–C7 = 13.32 (13)°. The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987) and are comparable to the related structures (Fun et al., 2007, 2009, 2010).

In the crystal packing (Fig. 2), N—H···O intermolecular hydrogen bonds (Table 1) connected the molecules into one dimensional chains along the [0 0 1] direction. The crystal is consolidated by short N···O [2.9758 (11) Å] contact, as well as by N—H···O hydrogen bonds, C—H···O and C—H···π (Table 1) and π–π interactions with the distances of Cg1···Cg1^iv = 3.8613 (6) Å Cg1···Cg2^iv = 3.5924 (6) Å and Cg2···Cg3^iv = 3.6576 (6) Å [symmetry code: (iv) 1/2 - x, 1/2 - y, 1 - z; Cg1, Cg2 and Cg3 are the centroids of the C9–C12/N1, C1–C4/C11/C12 and C5–C10 rings, respectively]. .

Related literature top

For bond-length data, see: Allen et al. (1987). For background to carbazole alkaloids and their activities, see: 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); Thongthoom et al. (2010); Yenjai et al. (2000). For related structures, see: Fun et al. (2007, 2009, 2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The air dried roots of C. lansium (2.92 kg) were successively extracted with acetone over the period of 3 days at room temperature. The solvent was removed under reduced pressure to provide the acetone extract (61.46 g) which was subjected to quick column chromatography (QCC) over silica gel and eluted with a gradient of hexanes-EtOAc (100% hexane to 100% EtOAc) to provide eight fractions (A—H). Fraction C (14.79 g) was further separated by sephadex LH-20 with CH₃OH to give six subfractions (C1—6). Subfraction C4 (5.70 g) was subjected to repeated QCC using 20% hexanes-EtOAc yielding the title compound (I) (19.6 mg). Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystallized from CH₂Cl₂/acetone (1:4, v/v) after several days, Mp 469.6–470.7 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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.
	Fig. 2. The crystal packing of the title compound viewed along the b axis, showing one dimensional chains along the [0 0 1] direction. Hydrogen bonds are shown as dashed lines.

2,7-Dimethoxy-9H-carbazole-3-carbaldehyde top

Crystal data top

C₁₅H₁₃NO₃	F(000) = 1072
M_r = 255.26	D_x = 1.461 Mg m⁻³
Monoclinic, C2/c	Melting point = 469.6–470.7 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 20.5756 (4) Å	Cell parameters from 3381 reflections
b = 8.1298 (1) Å	θ = 2.0–30.0°
c = 14.0411 (3) Å	µ = 0.10 mm⁻¹
β = 98.871 (1)°	T = 100 K
V = 2320.64 (7) Å³	Block, yellow
Z = 8	0.53 × 0.42 × 0.16 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3381 independent reflections
Radiation source: sealed tube	3032 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −28→28
T_min = 0.947, T_max = 0.984	k = −11→9
13003 measured reflections	l = −19→15

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) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0682P)² + 1.6186P] where P = (F_o² + 2F_c²)/3
3381 reflections	(Δ/σ)_max = 0.001
178 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₃NO₃	V = 2320.64 (7) Å³
M_r = 255.26	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.5756 (4) Å	µ = 0.10 mm⁻¹
b = 8.1298 (1) Å	T = 100 K
c = 14.0411 (3) Å	0.53 × 0.42 × 0.16 mm
β = 98.871 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3381 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3032 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.984	R_int = 0.020
13003 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.45 e Å⁻³
3381 reflections	Δρ_min = −0.24 e Å⁻³
178 parameters

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 120.0 (1) K.

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
O1	0.06869 (4)	0.45177 (10)	0.60778 (5)	0.01915 (17)
O2	0.01915 (4)	0.13634 (10)	0.39162 (6)	0.02408 (18)
O3	0.34527 (3)	0.26588 (9)	0.16940 (5)	0.01588 (16)
N1	0.27840 (4)	0.55708 (10)	0.49606 (6)	0.01503 (17)
H1N1	0.2977 (8)	0.626 (2)	0.5410 (12)	0.031 (4)*
C1	0.17456 (5)	0.51795 (12)	0.56255 (7)	0.01507 (18)
H1A	0.1855	0.5922	0.6148	0.018*
C2	0.11513 (5)	0.43366 (12)	0.54868 (7)	0.01486 (19)
C3	0.09900 (5)	0.32215 (12)	0.47030 (7)	0.01479 (18)
C4	0.14322 (5)	0.29659 (12)	0.40535 (7)	0.01420 (18)
H4A	0.1325	0.2221	0.3532	0.017*
C5	0.27380 (4)	0.30870 (12)	0.28279 (7)	0.01392 (18)
H5A	0.2440	0.2330	0.2479	0.017*
C6	0.33378 (5)	0.34504 (12)	0.25284 (7)	0.01366 (18)
C7	0.37905 (5)	0.45348 (12)	0.30457 (7)	0.01510 (18)
H7A	0.4196	0.4759	0.2826	0.018*
C8	0.36473 (5)	0.52877 (12)	0.38837 (7)	0.01506 (19)
H8A	0.3955	0.6003	0.4248	0.018*
C9	0.30431 (5)	0.49645 (12)	0.41708 (7)	0.01365 (18)
C10	0.25861 (4)	0.38624 (11)	0.36532 (6)	0.01310 (18)
C11	0.20281 (4)	0.38018 (11)	0.41712 (6)	0.01329 (18)
C12	0.21752 (4)	0.48914 (11)	0.49667 (7)	0.01357 (18)
C13	0.08690 (5)	0.55135 (13)	0.69203 (7)	0.0199 (2)
H13A	0.0510	0.5519	0.7305	0.030*
H13B	0.0955	0.6641	0.6726	0.030*
H13C	0.1266	0.5061	0.7306	0.030*
C14	0.03699 (5)	0.23074 (13)	0.45831 (8)	0.0192 (2)
H14A	0.0089	0.2457	0.5053	0.023*
C15	0.41126 (5)	0.27000 (14)	0.14839 (8)	0.0200 (2)
H15A	0.4153	0.1932	0.0958	0.030*
H15B	0.4419	0.2380	0.2059	0.030*
H15C	0.4217	0.3816	0.1291	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0164 (3)	0.0238 (4)	0.0186 (4)	−0.0010 (3)	0.0070 (3)	−0.0029 (3)
O2	0.0178 (4)	0.0251 (4)	0.0294 (4)	−0.0050 (3)	0.0038 (3)	−0.0061 (3)
O3	0.0146 (3)	0.0201 (3)	0.0135 (3)	0.0005 (2)	0.0042 (2)	−0.0016 (2)
N1	0.0141 (4)	0.0167 (4)	0.0145 (4)	−0.0030 (3)	0.0028 (3)	−0.0026 (3)
C1	0.0157 (4)	0.0159 (4)	0.0137 (4)	−0.0003 (3)	0.0025 (3)	−0.0008 (3)
C2	0.0142 (4)	0.0162 (4)	0.0147 (4)	0.0011 (3)	0.0039 (3)	0.0015 (3)
C3	0.0135 (4)	0.0156 (4)	0.0154 (4)	−0.0007 (3)	0.0025 (3)	0.0012 (3)
C4	0.0144 (4)	0.0145 (4)	0.0136 (4)	−0.0010 (3)	0.0017 (3)	0.0007 (3)
C5	0.0139 (4)	0.0143 (4)	0.0134 (4)	−0.0007 (3)	0.0018 (3)	0.0004 (3)
C6	0.0149 (4)	0.0145 (4)	0.0118 (4)	0.0013 (3)	0.0029 (3)	0.0010 (3)
C7	0.0133 (4)	0.0164 (4)	0.0157 (4)	−0.0014 (3)	0.0029 (3)	0.0016 (3)
C8	0.0143 (4)	0.0156 (4)	0.0152 (4)	−0.0026 (3)	0.0021 (3)	0.0004 (3)
C9	0.0138 (4)	0.0137 (4)	0.0133 (4)	−0.0004 (3)	0.0018 (3)	0.0006 (3)
C10	0.0129 (4)	0.0138 (4)	0.0127 (4)	−0.0006 (3)	0.0021 (3)	0.0014 (3)
C11	0.0134 (4)	0.0143 (4)	0.0123 (4)	−0.0004 (3)	0.0024 (3)	0.0008 (3)
C12	0.0132 (4)	0.0140 (4)	0.0133 (4)	−0.0003 (3)	0.0015 (3)	0.0012 (3)
C13	0.0226 (5)	0.0206 (5)	0.0178 (5)	0.0012 (4)	0.0074 (4)	−0.0015 (4)
C14	0.0143 (4)	0.0206 (5)	0.0232 (5)	−0.0019 (3)	0.0047 (3)	−0.0002 (4)
C15	0.0166 (4)	0.0243 (5)	0.0204 (5)	−0.0012 (4)	0.0073 (4)	−0.0016 (4)

Geometric parameters (Å, º) top

O1—C2	1.3667 (11)	C5—C10	1.3962 (13)
O1—C13	1.4347 (13)	C5—H5A	0.9500
O2—C14	1.2225 (13)	C6—C7	1.4013 (13)
O3—C6	1.3887 (11)	C7—C8	1.3975 (13)
O3—C15	1.4337 (11)	C7—H7A	0.9500
N1—C12	1.3702 (11)	C8—C9	1.3896 (13)
N1—C9	1.3927 (12)	C8—H8A	0.9500
N1—H1N1	0.890 (17)	C9—C10	1.4158 (13)
C1—C2	1.3890 (13)	C10—C11	1.4516 (12)
C1—C12	1.3944 (13)	C11—C12	1.4212 (13)
C1—H1A	0.9500	C13—H13A	0.9800
C2—C3	1.4250 (13)	C13—H13B	0.9800
C3—C4	1.3995 (13)	C13—H13C	0.9800
C3—C14	1.4637 (13)	C14—H14A	0.9500
C4—C11	1.3892 (13)	C15—H15A	0.9800
C4—H4A	0.9500	C15—H15B	0.9800
C5—C6	1.3954 (12)	C15—H15C	0.9800

C2—O1—C13	116.31 (8)	C7—C8—H8A	120.8
C6—O3—C15	116.91 (8)	C8—C9—N1	129.31 (9)
C12—N1—C9	108.96 (8)	C8—C9—C10	121.59 (9)
C12—N1—H1N1	123.8 (11)	N1—C9—C10	109.10 (8)
C9—N1—H1N1	127.2 (11)	C5—C10—C9	119.72 (8)
C2—C1—C12	117.29 (9)	C5—C10—C11	134.11 (8)
C2—C1—H1A	121.4	C9—C10—C11	106.16 (8)
C12—C1—H1A	121.4	C4—C11—C12	118.40 (8)
O1—C2—C1	122.99 (9)	C4—C11—C10	135.13 (9)
O1—C2—C3	115.86 (8)	C12—C11—C10	106.47 (8)
C1—C2—C3	121.15 (9)	N1—C12—C1	127.59 (9)
C4—C3—C2	120.03 (9)	N1—C12—C11	109.30 (8)
C4—C3—C14	119.50 (9)	C1—C12—C11	123.10 (9)
C2—C3—C14	120.45 (9)	O1—C13—H13A	109.5
C11—C4—C3	120.02 (9)	O1—C13—H13B	109.5
C11—C4—H4A	120.0	H13A—C13—H13B	109.5
C3—C4—H4A	120.0	O1—C13—H13C	109.5
C6—C5—C10	118.43 (8)	H13A—C13—H13C	109.5
C6—C5—H5A	120.8	H13B—C13—H13C	109.5
C10—C5—H5A	120.8	O2—C14—C3	124.07 (10)
O3—C6—C5	115.45 (8)	O2—C14—H14A	118.0
O3—C6—C7	122.88 (8)	C3—C14—H14A	118.0
C5—C6—C7	121.67 (9)	O3—C15—H15A	109.5
C8—C7—C6	120.15 (8)	O3—C15—H15B	109.5
C8—C7—H7A	119.9	H15A—C15—H15B	109.5
C6—C7—H7A	119.9	O3—C15—H15C	109.5
C9—C8—C7	118.40 (9)	H15A—C15—H15C	109.5
C9—C8—H8A	120.8	H15B—C15—H15C	109.5

C13—O1—C2—C1	−6.03 (14)	C6—C5—C10—C11	179.98 (10)
C13—O1—C2—C3	174.23 (8)	C8—C9—C10—C5	−0.65 (14)
C12—C1—C2—O1	−179.61 (9)	N1—C9—C10—C5	−179.76 (8)
C12—C1—C2—C3	0.12 (14)	C8—C9—C10—C11	178.56 (9)
O1—C2—C3—C4	179.41 (8)	N1—C9—C10—C11	−0.55 (10)
C1—C2—C3—C4	−0.33 (14)	C3—C4—C11—C12	0.77 (14)
O1—C2—C3—C14	−2.02 (14)	C3—C4—C11—C10	−179.17 (10)
C1—C2—C3—C14	178.23 (9)	C5—C10—C11—C4	−0.18 (19)
C2—C3—C4—C11	−0.13 (14)	C9—C10—C11—C4	−179.22 (10)
C14—C3—C4—C11	−178.71 (9)	C5—C10—C11—C12	179.87 (10)
C15—O3—C6—C5	−166.26 (8)	C9—C10—C11—C12	0.83 (10)
C15—O3—C6—C7	13.32 (13)	C9—N1—C12—C1	−179.26 (9)
C10—C5—C6—O3	−178.94 (8)	C9—N1—C12—C11	0.49 (11)
C10—C5—C6—C7	1.47 (14)	C2—C1—C12—N1	−179.72 (9)
O3—C6—C7—C8	−179.69 (8)	C2—C1—C12—C11	0.56 (14)
C5—C6—C7—C8	−0.13 (14)	C4—C11—C12—N1	179.22 (8)
C6—C7—C8—C9	−1.58 (14)	C10—C11—C12—N1	−0.82 (10)
C7—C8—C9—N1	−179.11 (9)	C4—C11—C12—C1	−1.01 (14)
C7—C8—C9—C10	1.98 (14)	C10—C11—C12—C1	178.95 (9)
C12—N1—C9—C8	−178.97 (10)	C4—C3—C14—O2	−3.35 (16)
C12—N1—C9—C10	0.05 (11)	C2—C3—C14—O2	178.08 (10)
C6—C5—C10—C9	−1.08 (13)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C4/C11/C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3ⁱ	0.890 (17)	2.106 (17)	2.9758 (11)	165.2 (15)
C15—H15C···O2ⁱⁱ	0.98	2.44	3.3888 (14)	162
C15—H15A···Cg2ⁱⁱⁱ	0.98	2.91	3.6613 (12)	134

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₃
M_r	255.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	20.5756 (4), 8.1298 (1), 14.0411 (3)
β (°)	98.871 (1)
V (Å³)	2320.64 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.53 × 0.42 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.947, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	13003, 3381, 3032
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.115, 1.04
No. of reflections	3381
No. of parameters	178
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C4/C11/C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3ⁱ	0.890 (17)	2.106 (17)	2.9758 (11)	165.2 (15)
C15—H15C···O2ⁱⁱ	0.98	2.44	3.3888 (14)	162
C15—H15A···Cg2ⁱⁱⁱ	0.98	2.91	3.6613 (12)	134

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

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 thank Mae Fah Luang University and the Thailand Research Fund through the TRF-research scholar (grant No. RSA5280011) and the Royal Golden Jubilee PhD Program (grant No. PHD/0006/2552) for financial support. SC thanks the Prince of Songkla University for generous support through the Crystal Materials Research Unit. The authors also Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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Volume 67| Part 7| July 2011| Pages o1811-o1812

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