(E)-N-[2-(Biphenyl-4-ylvin­yl)phen­yl]furan-2-carboxamide

Kee, C.H.; Thomas, N.F.; Ariffin, A.; Awang, K.; Ng, S.W.

doi:10.1107/S1600536808034569

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2210

doi:10.1107/S1600536808034569

Open

access

(E)-N-[2-(Biphenyl-4-ylvinyl)phenyl]furan-2-carboxamide

Chin Hui Kee,^a Noel F. Thomas,^a Azhar Ariffin,^a Khalijah Awang ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 October 2008; accepted 23 October 2008; online 25 October 2008)

In the title molecule, C₂₅H₁₉NO₂, the furyl ring is twisted by 46.3 (1)° with respect to the phenylene ring bearing the amido group. In the stilbene unit, the two phenylene rings (i.e. the rings connected through the –CH=CH– fragment) are twisted by 59.2 (1)°; in the biphenylene unit, the two benzene rings are twisted by 35.5 (1)°. In the crystal structure, molecules are linked by an N—H⋯O_amido hydrogen bond into a zigzag chain running along the c axis.

Related literature

For the use of radical cations in heterocyclic synthesis, see: Thomas et al. (2004 , 2008 ).

Experimental

Crystal data

C₂₅H₁₉NO₂
M_r = 365.41
Monoclinic, P 2₁ /c
a = 10.9271 (2) Å
b = 19.7960 (4) Å
c = 8.7969 (1) Å
β = 92.374 (1)°
V = 1901.25 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 (2) K
0.40 × 0.35 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
13179 measured reflections
4356 independent reflections
3681 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.106
S = 1.04
4356 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.88	2.05	2.903 (1)	163
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034569/lh2714sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034569/lh2714Isup2.hkl

checkCIF report

Comment top

In our earlier studies, we reported the synthesis of some stilbene carboxamides whose radical chemistry we investigated (Thomas et al., 2004, 2008). In the present study, we have synthesized a new stilbene carboxamide that incorporates a furan unit (Scheme I, Fig. 1).

Related literature top

For the use of radical cations in heterocyclic synthesis, see: Thomas et al. (2004, 2008).

Experimental top

N-(2-Iodophenyl)furan-2-carboxamide (0.37 g, 1.2 mmol) was dissolved in DMF (20 ml) under a nitrogen atmosphere. The solution was heated to 373 K. Palladium acetate (3.2 mg, 0.014 mmol) was added followed by triethylamine (0.65 ml, 4.7 mmol) and 4-vinylbiphenyl (0.20 g, 1.21 mmol). The mixture was further heated for an hour. The solution was cooled and then mixed with saturated sodium chloride. The organic compound was extracted with ethyl acetate. The ethyl acetate solution was dried with sodium sulfate. The solvent was evaporated and the product purified by column chromatography. Single crystals were obtained by recrystallization from petroleum ether/dichloromethane.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₅H₁₉NO₂ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.

(E)-N-[2-(Biphenyl-4-ylvinyl)phenyl]furan-2-carboxamide top

Crystal data top

C₂₅H₁₉NO₂	F(000) = 768
M_r = 365.41	D_x = 1.277 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5580 reflections
a = 10.9271 (2) Å	θ = 2.5–28.2°
b = 19.7960 (4) Å	µ = 0.08 mm⁻¹
c = 8.7969 (1) Å	T = 100 K
β = 92.374 (1)°	Prism, colorless
V = 1901.25 (6) Å³	0.40 × 0.35 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3681 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
ω scans	h = −14→13
13179 measured reflections	k = −25→25
4356 independent reflections	l = −11→11

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) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0529P)² + 0.6489P] where P = (F_o² + 2F_c²)/3
4356 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₅H₁₉NO₂	V = 1901.25 (6) Å³
M_r = 365.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9271 (2) Å	µ = 0.08 mm⁻¹
b = 19.7960 (4) Å	T = 100 K
c = 8.7969 (1) Å	0.40 × 0.35 × 0.15 mm
β = 92.374 (1)°

Data collection top

Bruker SMART APEX diffractometer	3681 reflections with I > 2σ(I)
13179 measured reflections	R_int = 0.022
4356 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
4356 reflections	Δρ_min = −0.25 e Å⁻³
253 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.

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

	x	y	z	U_iso*/U_eq
O1	0.69066 (8)	0.17866 (4)	0.88070 (9)	0.0218 (2)
O2	0.56344 (8)	0.18549 (4)	0.50228 (9)	0.01969 (19)
N1	0.52573 (9)	0.25519 (5)	0.70226 (11)	0.0173 (2)
H1	0.5441	0.2651	0.7981	0.021*
C1	0.76833 (12)	0.13051 (7)	0.93850 (15)	0.0263 (3)
H1A	0.8056	0.1316	1.0380	0.032*
C2	0.78542 (12)	0.08127 (7)	0.83672 (16)	0.0274 (3)
H2	0.8347	0.0421	0.8510	0.033*
C3	0.71470 (11)	0.09950 (6)	0.70252 (15)	0.0221 (3)
H3	0.7080	0.0751	0.6096	0.027*
C4	0.65936 (11)	0.15860 (6)	0.73503 (13)	0.0171 (2)
C5	0.57830 (10)	0.20106 (6)	0.63762 (13)	0.0164 (2)
C6	0.44068 (11)	0.29656 (6)	0.61664 (13)	0.0168 (2)
C7	0.34268 (11)	0.26554 (6)	0.53871 (14)	0.0205 (3)
H7	0.3306	0.2183	0.5488	0.025*
C8	0.26273 (11)	0.30299 (7)	0.44657 (14)	0.0228 (3)
H8	0.1971	0.2814	0.3914	0.027*
C9	0.27890 (12)	0.37245 (7)	0.43514 (14)	0.0237 (3)
H9	0.2252	0.3984	0.3707	0.028*
C10	0.37337 (11)	0.40363 (6)	0.51779 (14)	0.0213 (3)
H10	0.3821	0.4513	0.5114	0.026*
C11	0.45663 (11)	0.36676 (6)	0.61073 (13)	0.0172 (2)
C12	0.55685 (11)	0.40039 (6)	0.69725 (13)	0.0176 (2)
H12	0.6298	0.3755	0.7193	0.021*
C13	0.55134 (11)	0.46414 (6)	0.74683 (13)	0.0182 (2)
H13	0.4776	0.4882	0.7240	0.022*
C14	0.64845 (11)	0.50049 (6)	0.83315 (13)	0.0168 (2)
C15	0.61548 (11)	0.55136 (6)	0.93372 (13)	0.0178 (2)
H15	0.5313	0.5613	0.9446	0.021*
C16	0.70291 (11)	0.58746 (6)	1.01760 (13)	0.0179 (2)
H16	0.6778	0.6198	1.0896	0.021*
C17	0.82804 (11)	0.57700 (6)	0.99805 (13)	0.0173 (2)
C18	0.86116 (11)	0.52600 (6)	0.89750 (13)	0.0185 (2)
H18	0.9454	0.5175	0.8830	0.022*
C19	0.77344 (11)	0.48767 (6)	0.81860 (13)	0.0184 (2)
H19	0.7984	0.4523	0.7539	0.022*
C20	0.91995 (11)	0.62106 (6)	1.07784 (13)	0.0177 (2)
C21	1.02722 (11)	0.64044 (6)	1.00799 (14)	0.0204 (3)
H21	1.0433	0.6235	0.9098	0.025*
C22	1.11036 (11)	0.68399 (6)	1.07977 (14)	0.0224 (3)
H22	1.1832	0.6962	1.0312	0.027*
C23	1.08758 (12)	0.70986 (7)	1.22235 (15)	0.0237 (3)
H23	1.1436	0.7405	1.2706	0.028*
C24	0.98214 (13)	0.69059 (7)	1.29408 (15)	0.0274 (3)
H24	0.9665	0.7078	1.3922	0.033*
C25	0.89957 (11)	0.64639 (7)	1.22295 (14)	0.0234 (3)
H25	0.8282	0.6332	1.2735	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0244 (4)	0.0254 (5)	0.0155 (4)	−0.0007 (4)	−0.0020 (3)	0.0003 (3)
O2	0.0252 (4)	0.0194 (4)	0.0144 (4)	0.0002 (3)	−0.0003 (3)	−0.0011 (3)
N1	0.0219 (5)	0.0164 (5)	0.0134 (4)	−0.0005 (4)	−0.0018 (4)	−0.0020 (4)
C1	0.0239 (6)	0.0339 (7)	0.0208 (6)	0.0012 (5)	−0.0029 (5)	0.0074 (5)
C2	0.0232 (6)	0.0279 (7)	0.0311 (7)	0.0034 (5)	0.0011 (5)	0.0086 (6)
C3	0.0225 (6)	0.0205 (6)	0.0236 (6)	−0.0005 (5)	0.0026 (5)	−0.0004 (5)
C4	0.0184 (5)	0.0181 (6)	0.0148 (5)	−0.0039 (4)	0.0013 (4)	0.0001 (4)
C5	0.0177 (5)	0.0147 (5)	0.0168 (5)	−0.0036 (4)	0.0020 (4)	0.0009 (4)
C6	0.0195 (5)	0.0177 (6)	0.0133 (5)	0.0009 (4)	0.0010 (4)	−0.0010 (4)
C7	0.0231 (6)	0.0183 (6)	0.0202 (6)	−0.0015 (5)	0.0011 (5)	−0.0032 (5)
C8	0.0209 (6)	0.0283 (7)	0.0189 (6)	−0.0029 (5)	−0.0021 (5)	−0.0039 (5)
C9	0.0242 (6)	0.0278 (7)	0.0188 (6)	0.0017 (5)	−0.0037 (5)	0.0041 (5)
C10	0.0252 (6)	0.0188 (6)	0.0198 (6)	−0.0007 (5)	0.0005 (5)	0.0030 (5)
C11	0.0199 (5)	0.0188 (6)	0.0131 (5)	−0.0010 (4)	0.0019 (4)	0.0003 (4)
C12	0.0188 (5)	0.0180 (6)	0.0161 (5)	−0.0009 (4)	0.0008 (4)	0.0025 (4)
C13	0.0188 (5)	0.0178 (6)	0.0177 (6)	−0.0010 (4)	0.0002 (4)	0.0016 (4)
C14	0.0202 (6)	0.0132 (5)	0.0170 (5)	−0.0014 (4)	−0.0006 (4)	0.0035 (4)
C15	0.0175 (5)	0.0156 (5)	0.0205 (6)	0.0002 (4)	0.0015 (4)	0.0028 (4)
C16	0.0215 (6)	0.0131 (5)	0.0191 (6)	0.0003 (4)	0.0023 (4)	0.0006 (4)
C17	0.0200 (6)	0.0149 (5)	0.0167 (5)	−0.0002 (4)	−0.0007 (4)	0.0035 (4)
C18	0.0176 (5)	0.0181 (6)	0.0198 (6)	0.0022 (4)	0.0001 (4)	0.0023 (5)
C19	0.0228 (6)	0.0147 (5)	0.0179 (6)	0.0020 (4)	0.0014 (4)	0.0002 (4)
C20	0.0188 (5)	0.0147 (5)	0.0195 (6)	0.0013 (4)	−0.0020 (4)	0.0013 (4)
C21	0.0213 (6)	0.0205 (6)	0.0195 (6)	0.0009 (5)	0.0012 (5)	−0.0007 (5)
C22	0.0194 (6)	0.0239 (6)	0.0240 (6)	−0.0029 (5)	0.0012 (5)	0.0031 (5)
C23	0.0235 (6)	0.0244 (6)	0.0228 (6)	−0.0053 (5)	−0.0039 (5)	−0.0015 (5)
C24	0.0279 (7)	0.0340 (7)	0.0202 (6)	−0.0058 (6)	0.0010 (5)	−0.0061 (5)
C25	0.0216 (6)	0.0280 (7)	0.0208 (6)	−0.0051 (5)	0.0024 (5)	−0.0005 (5)

Geometric parameters (Å, º) top

O1—C1	1.3607 (16)	C12—H12	0.9500
O1—C4	1.3714 (14)	C13—C14	1.4676 (16)
O2—C5	1.2340 (14)	C13—H13	0.9500
N1—C5	1.3523 (15)	C14—C15	1.3975 (16)
N1—C6	1.4295 (15)	C14—C19	1.4002 (16)
N1—H1	0.8800	C15—C16	1.3818 (17)
C1—C2	1.342 (2)	C15—H15	0.9500
C1—H1A	0.9500	C16—C17	1.4005 (16)
C2—C3	1.4302 (19)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.3996 (17)
C3—C4	1.3528 (17)	C17—C20	1.4845 (16)
C3—H3	0.9500	C18—C19	1.3860 (17)
C4—C5	1.4706 (16)	C18—H18	0.9500
C6—C7	1.3903 (17)	C19—H19	0.9500
C6—C11	1.4019 (16)	C20—C25	1.3979 (17)
C7—C8	1.3825 (18)	C20—C21	1.3994 (16)
C7—H7	0.9500	C21—C22	1.3856 (18)
C8—C9	1.3904 (19)	C21—H21	0.9500
C8—H8	0.9500	C22—C23	1.3869 (18)
C9—C10	1.3832 (18)	C22—H22	0.9500
C9—H9	0.9500	C23—C24	1.3897 (18)
C10—C11	1.4026 (17)	C23—H23	0.9500
C10—H10	0.9500	C24—C25	1.3872 (18)
C11—C12	1.4672 (16)	C24—H24	0.9500
C12—C13	1.3373 (17)	C25—H25	0.9500

C1—O1—C4	105.89 (10)	C12—C13—C14	126.16 (11)
C5—N1—C6	120.70 (10)	C12—C13—H13	116.9
C5—N1—H1	119.6	C14—C13—H13	116.9
C6—N1—H1	119.6	C15—C14—C19	117.80 (11)
C2—C1—O1	111.19 (11)	C15—C14—C13	118.76 (10)
C2—C1—H1A	124.4	C19—C14—C13	123.43 (11)
O1—C1—H1A	124.4	C16—C15—C14	121.34 (11)
C1—C2—C3	106.39 (12)	C16—C15—H15	119.3
C1—C2—H2	126.8	C14—C15—H15	119.3
C3—C2—H2	126.8	C15—C16—C17	120.99 (11)
C4—C3—C2	105.94 (12)	C15—C16—H16	119.5
C4—C3—H3	127.0	C17—C16—H16	119.5
C2—C3—H3	127.0	C18—C17—C16	117.61 (11)
C3—C4—O1	110.59 (11)	C18—C17—C20	122.35 (10)
C3—C4—C5	129.40 (11)	C16—C17—C20	119.99 (10)
O1—C4—C5	119.99 (10)	C19—C18—C17	121.32 (11)
O2—C5—N1	124.22 (11)	C19—C18—H18	119.3
O2—C5—C4	118.13 (10)	C17—C18—H18	119.3
N1—C5—C4	117.65 (10)	C18—C19—C14	120.80 (11)
C7—C6—C11	120.92 (11)	C18—C19—H19	119.6
C7—C6—N1	118.52 (10)	C14—C19—H19	119.6
C11—C6—N1	120.55 (10)	C25—C20—C21	118.08 (11)
C8—C7—C6	120.50 (11)	C25—C20—C17	120.81 (10)
C8—C7—H7	119.8	C21—C20—C17	121.06 (10)
C6—C7—H7	119.8	C22—C21—C20	121.05 (11)
C7—C8—C9	119.57 (12)	C22—C21—H21	119.5
C7—C8—H8	120.2	C20—C21—H21	119.5
C9—C8—H8	120.2	C21—C22—C23	120.20 (11)
C10—C9—C8	119.85 (12)	C21—C22—H22	119.9
C10—C9—H9	120.1	C23—C22—H22	119.9
C8—C9—H9	120.1	C22—C23—C24	119.50 (12)
C9—C10—C11	121.74 (11)	C22—C23—H23	120.2
C9—C10—H10	119.1	C24—C23—H23	120.2
C11—C10—H10	119.1	C25—C24—C23	120.29 (12)
C6—C11—C10	117.32 (11)	C25—C24—H24	119.9
C6—C11—C12	121.45 (11)	C23—C24—H24	119.9
C10—C11—C12	121.22 (11)	C24—C25—C20	120.85 (11)
C13—C12—C11	123.68 (11)	C24—C25—H25	119.6
C13—C12—H12	118.2	C20—C25—H25	119.6
C11—C12—H12	118.2

C4—O1—C1—C2	−0.80 (14)	C10—C11—C12—C13	28.50 (17)
O1—C1—C2—C3	0.80 (15)	C11—C12—C13—C14	−179.77 (10)
C1—C2—C3—C4	−0.48 (14)	C12—C13—C14—C15	−150.97 (12)
C2—C3—C4—O1	0.00 (14)	C12—C13—C14—C19	30.06 (18)
C2—C3—C4—C5	178.41 (11)	C19—C14—C15—C16	−0.73 (17)
C1—O1—C4—C3	0.47 (13)	C13—C14—C15—C16	−179.76 (10)
C1—O1—C4—C5	−178.11 (10)	C14—C15—C16—C17	3.81 (17)
C6—N1—C5—O2	4.14 (17)	C15—C16—C17—C18	−3.75 (17)
C6—N1—C5—C4	−176.54 (10)	C15—C16—C17—C20	173.84 (10)
C3—C4—C5—O2	−6.48 (18)	C16—C17—C18—C19	0.74 (17)
O1—C4—C5—O2	171.80 (10)	C20—C17—C18—C19	−176.79 (11)
C3—C4—C5—N1	174.16 (12)	C17—C18—C19—C14	2.28 (18)
O1—C4—C5—N1	−7.56 (15)	C15—C14—C19—C18	−2.28 (17)
C5—N1—C6—C7	51.61 (15)	C13—C14—C19—C18	176.70 (11)
C5—N1—C6—C11	−127.90 (12)	C18—C17—C20—C25	−148.23 (12)
C11—C6—C7—C8	3.72 (17)	C16—C17—C20—C25	34.29 (17)
N1—C6—C7—C8	−175.79 (10)	C18—C17—C20—C21	34.12 (17)
C6—C7—C8—C9	−1.66 (18)	C16—C17—C20—C21	−143.35 (12)
C7—C8—C9—C10	−1.08 (18)	C25—C20—C21—C22	−0.62 (18)
C8—C9—C10—C11	1.85 (18)	C17—C20—C21—C22	177.09 (11)
C7—C6—C11—C10	−2.91 (16)	C20—C21—C22—C23	−0.77 (19)
N1—C6—C11—C10	176.59 (10)	C21—C22—C23—C24	1.4 (2)
C7—C6—C11—C12	177.55 (10)	C22—C23—C24—C25	−0.7 (2)
N1—C6—C11—C12	−2.95 (16)	C23—C24—C25—C20	−0.7 (2)
C9—C10—C11—C6	0.14 (17)	C21—C20—C25—C24	1.35 (19)
C9—C10—C11—C12	179.68 (11)	C17—C20—C25—C24	−176.37 (12)
C6—C11—C12—C13	−151.98 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88	2.05	2.903 (1)	163

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₉NO₂
M_r	365.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.9271 (2), 19.7960 (4), 8.7969 (1)
β (°)	92.374 (1)
V (Å³)	1901.25 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.35 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13179, 4356, 3681
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.106, 1.04
No. of reflections	4356
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88	2.05	2.903 (1)	163

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

We thank the Ministry of Science, Technology & Innovation (MOSTI) for supporting this study; CHK thanks MOSTI for an NSF scholarship.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomas, N. F., Kee, C.-H., Ariffin, A., Awang, K., Weber, J.-F. F., Lim, C.-G., Mukhtar, M. R. & Abdul Hadi, A. H. (2008). Heterocycles, 75, 1097–1108. CAS Google Scholar
Thomas, N. F., Velu, S. S., Weber, J.-F. F., Lee, K. C., Abdul Hadi, A. H., Richomme, P., Rondeau, D., Noorbatcha, I. & Awang, K. (2004). Tetrahedron, 51, 11733–11742. Web of Science CrossRef Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar