4-Hydr­oxy-5-(4-methoxy­phen­yl)pyrrolidin-2-one

Mohammat, M.F.; Shaameri, Z.; Hamzah, A.S.; Fun, H.-K.; Chantrapromma, S.

doi:10.1107/S1600536808003899

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages o578-o579

doi:10.1107/S1600536808003899

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4-Hydroxy-5-(4-methoxyphenyl)pyrrolidin-2-one

M. Fazli Mohammat,^a Zurina Shaameri,^a A. Sazali Hamzah,^a Hoong-Kun Fun ^b ^* and Suchada Chantrapromma ^c ‡

^aInstitute of Science, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 4 February 2008; accepted 6 February 2008; online 13 February 2008)

In the title compound, C₁₁H₁₃NO₃, the pyrrolidin-2-one ring is in an envelope conformation with the hydroxyl and 4-methoxyphenyl substituents mutually cis. The methoxy group is slighty twisted away from the mean plane of the attached benzene ring. The molecules are arranged into screw chains along the c axis. These chains are interconnected via intermolecular O—H⋯O and N—H⋯O hydrogen bonds into sheets parallel to the ac plane. The crystal structure is further stabilized by weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For details of ring conformations, see: Cremer & Pople (1975 ). For the biological properties of pyrrolidine alkaloids, see for example: Iida et al. (1986 ); Royles (1996 ). For the syntheses of compounds containing the tetramic acid ring, see for example: Chandrasekhar et al. (2006 ); Gurjar et al. (2006 ); Yoda et al. (1996 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₃NO₃
M_r = 207.22
Orthorhombic, P c a 2₁
a = 11.9862 (6) Å
b = 11.6251 (6) Å
c = 7.1539 (4) Å
V = 996.83 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100.0 (1) K
0.43 × 0.20 × 0.17 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.958, T_max = 0.983
8681 measured reflections
1562 independent reflections
1218 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.109
S = 1.09
1562 reflections
145 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2ⁱ	0.88 (4)	2.05 (4)	2.917 (3)	167 (4)
O2—H1O2⋯O3ⁱⁱ	0.90 (4)	1.98 (4)	2.800 (2)	152 (3)
C3—H3A⋯O1ⁱⁱⁱ	0.98	2.33	3.193 (3)	146
C11—H11A⋯O1^iv	0.96	2.49	3.395 (3)	158
C6—H6A⋯Cg1^v	0.93	2.81	3.514 (3)	133
C9—H9A⋯Cg1^vi	0.93	2.68	3.554 (3)	157
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[-x+2, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+2, z]$ ; (iv) $[-x+{\script{3\over 2}}, y-1, z-{\script{1\over 2}}]$ ; (v) $[x+{\script{3\over 2}}, -y, z]$ ; (vi) $[-x+2, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003899/sj2463sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003899/sj2463Isup2.hkl

checkCIF report

Comment top

Many naturally occurring compounds containing a tetramic acid ring system such as radicamine, fuligorobin and codonopsinine possess potent antibiotic, antiviral, antifungal, cytotoxic (Royles, 1996) as well as hypotensive activities (Iida et al., 1986). The title compound, C₁₁H₁₃NO₃, can act as an essential intermediate in the synthesis of such tetramic acid derivatives (Chandrasekhar et al., 2006; Gurjar et al., 2006; Yoda et al., 1996), which eventually can be used as a template in multi-step syntheses of biologically active natural products. We have synthesized the title compound (I) and its structure is reported here, Fig. 1.

In (I), the pyrrolidine-2-one ring adopts an envelope conformation with atom C3 displaced from the C1/C2/C3/N1 plane by 0.219 (3) Å, and with puckering parameters (Cremer & Pople, 1975) Q = 0.357 (3) Å and ϕ = 117.9 (4)°. The bond angles around C1 atom are indicative of sp² hybridization. The hydroxyl and 4-methoxyphenyl substituents are attached to the pyrrolidin-2-one ring at atom C3 and C4, respectively and is in cis-configuration (Fig. 1). The methoxy group is slightly twisted away from the mean plane of the phenyl ring as shown by the torsion angle C11–O3–C8–C7 = -5.2 (4)° All bond lengths and angles show normal values (Allen et al., 1987)

In the crystal packing of the title compound (Fig. 2), the molecules are arranged into screw chains along the c direction. These chains are interconnected via intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) into sheets parallel to the ac plane. The crystal is further stabilized by weak intermolecular C—H···O and C—H···π interactions; C6—H6A···Cg₁ (symmetry code: 3/2 - x, y, 1/2 + z) and C9—H9A··· Cg₁ (symmetry code: 2 - x, 1 - y, -1/2 + z), Cg₁ is the centroid of C5–C10 phenyl ring.

Related literature top

For details of ring conformations, see: Cremer & Pople (1975). For the biological properties of pyrrolidine alkaloids, see for example Iida et al. (1986); Royles (1996). For the syntheses of compounds containing the tetramic acid ring, see for example Chandrasekhar et al. (2006); Gurjar et al. (2006); Yoda et al. (1996). Forbond-length data, see: Allen et al. (1987).

Experimental top

The synthetic approach to the title compound began with the esterification of p-hydroxyphenylglycine (10.00 g, 60.10 mmol) and thionyl chloride in methanol to give the ester product (10.30 g, 95%). Amine protection (10.00 g, 54.9 mmol) was then carried out using tert-butoxycarbonyl (Boc₂O) and triethylamine (Et₃N) in tetrahydrofuran (THF) to give the N-Boc protected product in 85% yield (13.12 g). The hydroxyl functional group (13.01 g, 46.66 mmol) was protected by converting it to the methyl ether using potassium carbonate and methyl iodide (12.72 g, 93%). Condensation between the N-Boc methyl ester (8.30 g, 28.30 mmol) and methyl malonyl chloride in equimolar amounts furnished an intermediate diester (10.60 g, 95%). Dieckmann cyclization of this intermediate diester (5.50 g, 13.99 mmol) with potassium tert-butoxide (t-BuOK) in toluene gave the carbon skeleton β,β diketoester in 45% yield (1.65 g). Demethoxycarbonylation of the β,β diketoester (0.30 g, 1.1 mmol) was successfully carried out by refluxing in 50 ml acetonitrile to give the basic pyrrolidinone ring skeleton (0.23 g, 99%). Reduction of this diketone (0.16 g, 0.77 mmol) was then carried out in sodium borohydride/methanol at 273 K to give the title compound (0.04 g, 24%). Single crystals suitable for X-ray structure determination were obtained by slow evaporation of an ethyl acetate-petroleum ether (2:1 v/v) solution after several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (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, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of (I), viewed along the b axis. Hydrogen bonds were drawn as dashed lines.

4-hydroxy-5-(4-methoxyphenyl)pyrrolidin-2-one top

Crystal data top

C₁₁H₁₃NO₃	F(000) = 440
M_r = 207.22	D_x = 1.381 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1562 reflections
a = 11.9862 (6) Å	θ = 1.8–30.0°
b = 11.6251 (6) Å	µ = 0.10 mm⁻¹
c = 7.1539 (4) Å	T = 100 K
V = 996.83 (9) Å³	Block, colorless
Z = 4	0.43 × 0.20 × 0.17 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	1562 independent reflections
Radiation source: fine-focus sealed tube	1218 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.8°
ω scans	h = −16→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
T_min = 0.958, T_max = 0.983	l = −10→9
8681 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0466P)² + 0.0367P] where P = (F_o² + 2F_c²)/3
1562 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₁H₁₃NO₃	V = 996.83 (9) Å³
M_r = 207.22	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 11.9862 (6) Å	µ = 0.10 mm⁻¹
b = 11.6251 (6) Å	T = 100 K
c = 7.1539 (4) Å	0.43 × 0.20 × 0.17 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	1562 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1218 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.983	R_int = 0.066
8681 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.22 e Å⁻³
1562 reflections	Δρ_min = −0.24 e Å⁻³
145 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.69354 (13)	1.02873 (16)	1.1878 (3)	0.0282 (5)
O2	0.93282 (14)	0.80442 (16)	1.3464 (3)	0.0238 (4)
H1O2	0.977 (3)	0.742 (3)	1.345 (6)	0.045 (10)*
O3	0.87847 (13)	0.33500 (15)	0.8900 (3)	0.0239 (4)
N1	0.76602 (18)	0.86418 (18)	1.0604 (3)	0.0228 (5)
H1N1	0.704 (3)	0.838 (3)	1.009 (6)	0.043 (10)*
C1	0.7727 (2)	0.9651 (2)	1.1524 (4)	0.0223 (6)
C2	0.89395 (19)	0.9844 (2)	1.2029 (5)	0.0243 (6)
H2A	0.9012	1.0105	1.3311	0.029*
H2B	0.9279	1.0408	1.1206	0.029*
C3	0.94736 (19)	0.8665 (2)	1.1771 (4)	0.0222 (6)
H3A	1.0262	0.8725	1.1423	0.027*
C4	0.8761 (2)	0.8158 (2)	1.0169 (4)	0.0207 (6)
H4A	0.9018	0.8495	0.8989	0.025*
C5	0.8762 (2)	0.6876 (2)	0.9962 (4)	0.0199 (6)
C6	0.79693 (19)	0.6171 (2)	1.0788 (4)	0.0221 (6)
H6A	0.7435	0.6497	1.1568	0.027*
C7	0.79523 (19)	0.4993 (2)	1.0483 (4)	0.0229 (6)
H7A	0.7403	0.4538	1.1030	0.028*
C8	0.8756 (2)	0.4503 (2)	0.9363 (4)	0.0214 (6)
C9	0.95804 (18)	0.5175 (2)	0.8550 (4)	0.0226 (6)
H9A	1.0130	0.4839	0.7812	0.027*
C10	0.95734 (19)	0.6345 (2)	0.8850 (4)	0.0220 (6)
H10A	1.0124	0.6796	0.8298	0.026*
C11	0.7980 (2)	0.2604 (2)	0.9764 (5)	0.0287 (7)
H11A	0.8057	0.1841	0.9266	0.043*
H11B	0.7242	0.2885	0.9512	0.043*
H11C	0.8103	0.2588	1.1089	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0208 (9)	0.0270 (10)	0.0367 (12)	0.0068 (8)	−0.0016 (9)	−0.0014 (9)
O2	0.0184 (8)	0.0253 (10)	0.0276 (11)	0.0048 (8)	−0.0014 (8)	0.0003 (9)
O3	0.0211 (8)	0.0217 (9)	0.0288 (11)	0.0006 (7)	0.0017 (8)	−0.0027 (8)
N1	0.0133 (10)	0.0230 (11)	0.0321 (14)	0.0000 (9)	−0.0023 (10)	−0.0027 (10)
C1	0.0202 (12)	0.0228 (12)	0.0238 (16)	0.0016 (10)	−0.0008 (10)	0.0026 (12)
C2	0.0194 (12)	0.0219 (13)	0.0317 (16)	−0.0007 (10)	−0.0029 (11)	−0.0019 (12)
C3	0.0137 (11)	0.0240 (13)	0.0289 (14)	0.0009 (10)	0.0009 (11)	−0.0020 (12)
C4	0.0179 (12)	0.0200 (13)	0.0242 (14)	0.0006 (10)	−0.0001 (10)	−0.0017 (11)
C5	0.0137 (11)	0.0218 (13)	0.0243 (15)	0.0006 (10)	0.0000 (10)	0.0009 (11)
C6	0.0170 (11)	0.0255 (13)	0.0239 (14)	0.0016 (9)	0.0024 (11)	−0.0013 (12)
C7	0.0167 (12)	0.0243 (13)	0.0278 (15)	−0.0008 (10)	0.0027 (11)	0.0001 (12)
C8	0.0178 (12)	0.0212 (13)	0.0251 (15)	0.0021 (10)	−0.0030 (10)	−0.0015 (11)
C9	0.0173 (12)	0.0254 (13)	0.0252 (14)	0.0029 (9)	0.0040 (11)	−0.0021 (12)
C10	0.0170 (12)	0.0239 (13)	0.0251 (14)	−0.0011 (9)	0.0024 (11)	0.0013 (13)
C11	0.0250 (13)	0.0263 (15)	0.0346 (18)	−0.0003 (11)	0.0035 (12)	0.0030 (14)

Geometric parameters (Å, º) top

O1—C1	1.229 (3)	C4—H4A	0.9800
O2—C3	1.420 (3)	C5—C6	1.387 (4)
O2—H1O2	0.90 (3)	C5—C10	1.399 (4)
O3—C8	1.381 (3)	C6—C7	1.387 (4)
O3—C11	1.437 (3)	C6—H6A	0.9300
N1—C1	1.347 (3)	C7—C8	1.376 (4)
N1—C4	1.468 (3)	C7—H7A	0.9300
N1—H1N1	0.88 (4)	C8—C9	1.387 (3)
C1—C2	1.515 (3)	C9—C10	1.378 (4)
C2—C3	1.524 (4)	C9—H9A	0.9300
C2—H2A	0.9700	C10—H10A	0.9300
C2—H2B	0.9700	C11—H11A	0.9600
C3—C4	1.547 (4)	C11—H11B	0.9600
C3—H3A	0.9800	C11—H11C	0.9600
C4—C5	1.498 (3)

C3—O2—H1O2	109 (3)	C3—C4—H4A	108.2
C8—O3—C11	117.8 (2)	C6—C5—C10	117.2 (2)
C1—N1—C4	112.6 (2)	C6—C5—C4	123.0 (2)
C1—N1—H1N1	123 (2)	C10—C5—C4	119.7 (2)
C4—N1—H1N1	123 (2)	C7—C6—C5	121.8 (2)
O1—C1—N1	125.4 (2)	C7—C6—H6A	119.1
O1—C1—C2	127.0 (2)	C5—C6—H6A	119.1
N1—C1—C2	107.6 (2)	C8—C7—C6	119.3 (2)
C1—C2—C3	103.9 (2)	C8—C7—H7A	120.3
C1—C2—H2A	111.0	C6—C7—H7A	120.3
C3—C2—H2A	111.0	C7—C8—O3	124.0 (2)
C1—C2—H2B	111.0	C7—C8—C9	120.7 (2)
C3—C2—H2B	111.0	O3—C8—C9	115.3 (2)
H2A—C2—H2B	109.0	C10—C9—C8	119.1 (2)
O2—C3—C2	107.6 (2)	C10—C9—H9A	120.5
O2—C3—C4	111.8 (2)	C8—C9—H9A	120.5
C2—C3—C4	101.6 (2)	C9—C10—C5	121.9 (2)
O2—C3—H3A	111.8	C9—C10—H10A	119.1
C2—C3—H3A	111.8	C5—C10—H10A	119.1
C4—C3—H3A	111.8	O3—C11—H11A	109.5
N1—C4—C5	113.8 (2)	O3—C11—H11B	109.5
N1—C4—C3	101.1 (2)	H11A—C11—H11B	109.5
C5—C4—C3	116.9 (2)	O3—C11—H11C	109.5
N1—C4—H4A	108.2	H11A—C11—H11C	109.5
C5—C4—H4A	108.2	H11B—C11—H11C	109.5

C4—N1—C1—O1	172.0 (3)	N1—C4—C5—C10	154.0 (2)
C4—N1—C1—C2	−8.0 (3)	C3—C4—C5—C10	−88.6 (3)
O1—C1—C2—C3	164.1 (3)	C10—C5—C6—C7	−2.1 (4)
N1—C1—C2—C3	−15.8 (3)	C4—C5—C6—C7	176.1 (3)
C1—C2—C3—O2	−86.1 (3)	C5—C6—C7—C8	1.4 (4)
C1—C2—C3—C4	31.4 (3)	C6—C7—C8—O3	−176.9 (2)
C1—N1—C4—C5	154.0 (2)	C6—C7—C8—C9	0.3 (4)
C1—N1—C4—C3	27.9 (3)	C11—O3—C8—C7	−5.2 (4)
O2—C3—C4—N1	79.4 (2)	C11—O3—C8—C9	177.4 (2)
C2—C3—C4—N1	−35.1 (2)	C7—C8—C9—C10	−1.2 (4)
O2—C3—C4—C5	−44.7 (3)	O3—C8—C9—C10	176.3 (2)
C2—C3—C4—C5	−159.2 (2)	C8—C9—C10—C5	0.4 (4)
N1—C4—C5—C6	−24.2 (4)	C6—C5—C10—C9	1.2 (4)
C3—C4—C5—C6	93.2 (3)	C4—C5—C10—C9	−177.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.88 (4)	2.05 (4)	2.917 (3)	167 (4)
O2—H1O2···O3ⁱⁱ	0.90 (4)	1.98 (4)	2.800 (2)	152 (3)
C3—H3A···O1ⁱⁱⁱ	0.98	2.33	3.193 (3)	146
C11—H11A···O1^iv	0.96	2.49	3.395 (3)	158
C6—H6A···Cg1^v	0.93	2.81	3.514 (3)	133
C9—H9A···Cg1^vi	0.93	2.68	3.554 (3)	157

Symmetry codes: (i) −x+3/2, y, z−1/2; (ii) −x+2, −y+1, z+1/2; (iii) x+1/2, −y+2, z; (iv) −x+3/2, y−1, z−1/2; (v) x+3/2, −y, z; (vi) −x+2, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃NO₃
M_r	207.22
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	100
a, b, c (Å)	11.9862 (6), 11.6251 (6), 7.1539 (4)
V (Å³)	996.83 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.43 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.958, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	8681, 1562, 1218
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.109, 1.09
No. of reflections	1562
No. of parameters	145
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)	0.22, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.88 (4)	2.05 (4)	2.917 (3)	167 (4)
O2—H1O2···O3ⁱⁱ	0.90 (4)	1.98 (4)	2.800 (2)	152 (3)
C3—H3A···O1ⁱⁱⁱ	0.98	2.3340	3.193 (3)	146
C11—H11A···O1^iv	0.96	2.4861	3.395 (3)	158
C6—H6A···Cg1^v	0.93	2.8091	3.514 (3)	133
C9—H9A···Cg1^vi	0.93	2.6791	3.554 (3)	157

Symmetry codes: (i) −x+3/2, y, z−1/2; (ii) −x+2, −y+1, z+1/2; (iii) x+1/2, −y+2, z; (iv) −x+3/2, y−1, z−1/2; (v) x+3/2, −y, z; (vi) −x+2, −y+1, z−1/2.

Footnotes

‡Additional correspondence author, email: suchada.c@psu.ac.th.

Acknowledgements

The authors acknowledge the generous support of both the Universiti Teknologi MARA and Universiti Sains Malaysia as well as the financial support of the Ministry of Science, Technology and Innovation (E-Science grant No. SF0050–02-01–01). HKF and SC thank the Malaysian Government and Universiti Sains Malaysia for the Scientific Advancement Grant Allocation (SAGA) grant No. 304/PFIZIK/653003/A118.

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