2,5-Bis(4-meth­oxy­phen­yl)-1,3,4-oxadiazole

Fun, H.-K.; Goh, J.H.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536810044405

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3072

https://doi.org/10.1107/S1600536810044405

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2,5-Bis(4-methoxyphenyl)-1,3,4-oxadiazole

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a § Nithinchandra ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 28 October 2010; accepted 30 October 2010; online 6 November 2010)

In the title compound, C₁₆H₁₄N₂O₃, the essentially planar 1,3,4-oxadiazole ring [maximum deviation = 0.0021 (11) Å] is inclined at dihedral angles of 8.06 (6) and 11.21 (6)° with respect to the two benzene rings; the dihedral angle between the latter rings is 11.66 (5)°. In the crystal, short intermolecular C⋯O interactions [2.9968 (15) Å] connect adjacent molecules into chains propagating in [203]. The crystal structure is further stabilized by weak intermolecular C—H⋯π interactions.

Related literature

For general background to and applications of the title compound, see: Andersen et al. (1994 ); Clitherow et al. (1996 ); Hegde et al. (2008 ); Rai et al. (2008 ); Showell et al. (1991 ). For closely related 2,5-diphenyl-1,3,4-oxadiazole structures, see: Reck et al. (2003a ,b ); Franco et al. (2003 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₃
M_r = 282.29
Monoclinic, P 2₁ /c
a = 10.7525 (2) Å
b = 11.8973 (2) Å
c = 11.6340 (2) Å
β = 115.434 (1)°
V = 1344.04 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.53 × 0.49 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.950, T_max = 0.992
17061 measured reflections
4744 independent reflections
3744 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.137
S = 1.03
4744 reflections
246 parameters
All H-atom parameters refined
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C9–C14 and C1–C6 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cg1ⁱ	1.031 (14)	2.563 (16)	3.4903 (14)	149.4 (10)
C15—H15B⋯Cg2ⁱⁱ	0.992 (14)	2.994 (16)	3.8804 (14)	149.4 (11)
Symmetry codes: (i) x-1, y, z-1; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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/S1600536810044405/hb5714sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044405/hb5714Isup2.hkl

checkCIF report

Comment top

Heterocyclic compounds are becoming increasingly important in recent years due to their pharmacological activities (Rai et al., 2008). Nitrogen- and oxygen-containing five/six-membered heterocyclic compounds are of enormous significance in the field of medicinal chemistry (Hegde et al., 2008). Oxadiazoles play a very vital role in the preparation of various biologically active drugs with anti-inflammatory (Andersen et al., 1994) and anti-cancer (Showell et al., 1991) activities. The results of biological studies showed that oxadiazole derivatives also possess significant anti-inflammatory, analgesic and minimum ulcerogenic and lipid per-oxidation (Clitherow et al., 1996) properties.

In the title oxadiazole compound (Fig. 1), the 1,3,4-oxadiazole ring (C7/C8/N1/N2/O1) is essentially planar, with a maximum deviation of -0.0021 (11) at atom N1. The C1-C6 and C9-C14 phenyl rings are inclined at dihedral angles of 11.21 (6) and 8.06 (6)°, respectively, with the 1,3,4-oxadiazole ring. The geometric parameters agree well with those observed in closely related 2,5-diphenyl-1,3,4-oxadiazole structures (Reck et al., 2003a,b; Franco et al., 2003).

In the crystal, no significant intermolecular hydrogen bond is observed. The interesting feature of the crystal structure is the intermolecular short C15···O3 interactions [2.9968 (15) Å, symmetry code: x+1, -y+1/2, z+3/2], which is significantly shorter than the sum of the Van der Waals radii of the relevant atoms (3.22 Å), interconnecting adjacent molecules into one-dimensional chains propagating along the [203] direction (Fig. 2). Further stabilization of the crystal structure is provided by weak intermolecular C15—H15A···Cg1 and C15—H15B···Cg2 interactions (Table 1) where Cg1 and Cg2 are the centroids of C9-C14 and C1-C6 phenyl rings, respectively.

Related literature top

For general background to and applications of the title compound, see: Andersen et al. (1994); Clitherow et al. (1996); Hegde et al. (2008); Rai et al. (2008); Showell et al. (1991). For closely related 2,5-diphenyl-1,3,4-oxadiazole structures, see: Reck et al. (2003a,b); Franco et al. (2003). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

An equimolar mixture of 4-methoxybenzoic acid (0.01 mol) and 4-methoxybenzhydrazide was dissolved in POCl₃ (25–30 ml) by gentle warming. The solution is refluxed for about 12 h. Excess of POCl₃ is distilled off, and then the reaction mixture is poured into crushed ice. The separated solid was filtered, washed with water and dried. It was then recrystallized from ethanol. Yellow blocks of (I) were obtained from ethanol by slow evaporation.

Structure description top

For general background to and applications of the title compound, see: Andersen et al. (1994); Clitherow et al. (1996); Hegde et al. (2008); Rai et al. (2008); Showell et al. (1991). For closely related 2,5-diphenyl-1,3,4-oxadiazole structures, see: Reck et al. (2003a,b); Franco et al. (2003). 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 asymmetric unit of the title compound, showing 50 % probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis, showing molecules being interconnected into one-dimensional chains. H atoms have been omitted for clarity and intermolecular short interactions are shown as dashed lines.

2,5-Bis(4-methoxyphenyl)-1,3,4-oxadiazole top

Crystal data top

C₁₆H₁₄N₂O₃	F(000) = 592
M_r = 282.29	D_x = 1.395 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5014 reflections
a = 10.7525 (2) Å	θ = 2.6–32.2°
b = 11.8973 (2) Å	µ = 0.10 mm⁻¹
c = 11.6340 (2) Å	T = 100 K
β = 115.434 (1)°	Block, yellow
V = 1344.04 (4) Å³	0.53 × 0.49 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4744 independent reflections
Radiation source: fine-focus sealed tube	3744 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 32.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→15
T_min = 0.950, T_max = 0.992	k = −17→17
17061 measured reflections	l = −14→17

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) = 0.137	All H-atom parameters refined
S = 1.03	w = 1/[σ²(F_o²) + (0.079P)² + 0.1649P] where P = (F_o² + 2F_c²)/3
4744 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₄N₂O₃	V = 1344.04 (4) Å³
M_r = 282.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7525 (2) Å	µ = 0.10 mm⁻¹
b = 11.8973 (2) Å	T = 100 K
c = 11.6340 (2) Å	0.53 × 0.49 × 0.09 mm
β = 115.434 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4744 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3744 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.992	R_int = 0.027
17061 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.137	All H-atom parameters refined
S = 1.03	Δρ_max = 0.38 e Å⁻³
4744 reflections	Δρ_min = −0.30 e Å⁻³
246 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 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	0.89032 (6)	0.25303 (6)	0.21170 (6)	0.01974 (15)
O2	0.49848 (8)	0.12006 (7)	−0.35883 (8)	0.0333 (2)
O3	1.26608 (8)	0.16634 (6)	0.80451 (7)	0.02542 (17)
N1	0.84586 (9)	0.42831 (7)	0.14199 (9)	0.02542 (19)
N2	0.93713 (9)	0.43051 (7)	0.27255 (8)	0.02513 (19)
C1	0.64742 (10)	0.33907 (9)	−0.11316 (10)	0.0243 (2)
C2	0.56651 (10)	0.29145 (9)	−0.23102 (10)	0.0257 (2)
C3	0.57391 (10)	0.17639 (9)	−0.24904 (10)	0.0247 (2)
C4	0.66395 (10)	0.10958 (9)	−0.14829 (10)	0.0264 (2)
C5	0.74483 (10)	0.15763 (8)	−0.03171 (10)	0.0234 (2)
C6	0.73715 (9)	0.27300 (8)	−0.01231 (9)	0.02039 (18)
C7	0.82192 (9)	0.32333 (8)	0.11073 (9)	0.02031 (18)
C8	0.95953 (9)	0.32608 (7)	0.30883 (9)	0.01932 (18)
C9	1.04150 (9)	0.28123 (7)	0.43534 (9)	0.01863 (17)
C10	1.06169 (9)	0.16598 (8)	0.45607 (9)	0.01989 (18)
C11	1.13636 (9)	0.12351 (8)	0.57833 (9)	0.02060 (18)
C12	1.19097 (9)	0.19768 (8)	0.68094 (9)	0.01974 (18)
C13	1.17027 (10)	0.31372 (8)	0.66105 (10)	0.0232 (2)
C14	1.09745 (10)	0.35469 (8)	0.53959 (10)	0.02276 (19)
C15	0.42071 (11)	0.18563 (12)	−0.47047 (11)	0.0320 (2)
C16	1.29532 (13)	0.05018 (10)	0.82938 (11)	0.0312 (2)
H1A	0.6395 (13)	0.4157 (12)	−0.1004 (13)	0.031 (3)*
H2A	0.5040 (16)	0.3408 (13)	−0.2994 (15)	0.044 (4)*
H4A	0.6699 (14)	0.0323 (13)	−0.1637 (14)	0.034 (4)*
H5A	0.8051 (14)	0.1104 (12)	0.0334 (13)	0.033 (4)*
H10A	1.0288 (13)	0.1131 (11)	0.3879 (13)	0.028 (3)*
H11A	1.1508 (14)	0.0475 (12)	0.5874 (14)	0.033 (3)*
H13A	1.2011 (15)	0.3619 (13)	0.7306 (14)	0.039 (4)*
H14A	1.0822 (13)	0.4342 (12)	0.5266 (13)	0.031 (3)*
H15A	0.3446 (14)	0.2322 (11)	−0.4612 (13)	0.031 (3)*
H15B	0.4821 (14)	0.2357 (12)	−0.4910 (14)	0.030 (3)*
H15C	0.3802 (16)	0.1299 (14)	−0.5399 (15)	0.043 (4)*
H16A	1.2087 (16)	0.0060 (13)	0.8025 (15)	0.044 (4)*
H16B	1.3518 (15)	0.0229 (13)	0.7875 (14)	0.040 (4)*
H16C	1.3490 (16)	0.0457 (14)	0.9238 (16)	0.046 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0201 (3)	0.0161 (3)	0.0210 (3)	0.0006 (2)	0.0069 (2)	0.0022 (2)
O2	0.0298 (4)	0.0347 (4)	0.0238 (4)	−0.0009 (3)	0.0003 (3)	0.0011 (3)
O3	0.0325 (4)	0.0234 (4)	0.0183 (3)	0.0021 (3)	0.0089 (3)	0.0011 (3)
N1	0.0316 (4)	0.0193 (4)	0.0244 (4)	0.0024 (3)	0.0112 (3)	0.0035 (3)
N2	0.0324 (4)	0.0184 (4)	0.0236 (4)	0.0022 (3)	0.0111 (3)	0.0020 (3)
C1	0.0247 (4)	0.0219 (5)	0.0262 (5)	0.0025 (3)	0.0108 (4)	0.0062 (4)
C2	0.0220 (4)	0.0283 (5)	0.0246 (5)	0.0024 (3)	0.0080 (4)	0.0086 (4)
C3	0.0197 (4)	0.0282 (5)	0.0224 (4)	−0.0015 (3)	0.0054 (3)	0.0031 (4)
C4	0.0243 (4)	0.0222 (5)	0.0265 (5)	0.0002 (3)	0.0050 (4)	0.0023 (4)
C5	0.0210 (4)	0.0217 (4)	0.0237 (4)	0.0009 (3)	0.0058 (3)	0.0050 (3)
C6	0.0183 (4)	0.0213 (4)	0.0219 (4)	0.0005 (3)	0.0090 (3)	0.0045 (3)
C7	0.0204 (4)	0.0192 (4)	0.0223 (4)	0.0031 (3)	0.0101 (3)	0.0054 (3)
C8	0.0210 (4)	0.0165 (4)	0.0217 (4)	0.0007 (3)	0.0103 (3)	−0.0001 (3)
C9	0.0192 (4)	0.0161 (4)	0.0213 (4)	0.0001 (3)	0.0092 (3)	−0.0003 (3)
C10	0.0201 (4)	0.0161 (4)	0.0220 (4)	−0.0010 (3)	0.0076 (3)	−0.0020 (3)
C11	0.0222 (4)	0.0156 (4)	0.0228 (4)	−0.0009 (3)	0.0086 (3)	−0.0005 (3)
C12	0.0212 (4)	0.0206 (4)	0.0185 (4)	0.0006 (3)	0.0096 (3)	0.0004 (3)
C13	0.0284 (4)	0.0195 (4)	0.0223 (4)	0.0010 (3)	0.0113 (4)	−0.0039 (3)
C14	0.0275 (4)	0.0163 (4)	0.0246 (4)	0.0017 (3)	0.0112 (4)	−0.0015 (3)
C15	0.0237 (4)	0.0470 (7)	0.0213 (5)	0.0004 (4)	0.0059 (4)	0.0067 (4)
C16	0.0390 (6)	0.0239 (5)	0.0242 (5)	0.0018 (4)	0.0074 (4)	0.0053 (4)

Geometric parameters (Å, º) top

O1—C8	1.3652 (11)	C6—C7	1.4552 (13)
O1—C7	1.3704 (11)	C8—C9	1.4537 (13)
O2—C3	1.3597 (13)	C9—C10	1.3930 (12)
O2—C15	1.4359 (13)	C9—C14	1.4036 (13)
O3—C12	1.3641 (11)	C10—C11	1.3937 (13)
O3—C16	1.4193 (13)	C10—H10A	0.954 (14)
N1—C7	1.2954 (13)	C11—C12	1.3952 (13)
N1—N2	1.4110 (12)	C11—H11A	0.916 (14)
N2—C8	1.3010 (12)	C12—C13	1.4017 (14)
C1—C2	1.3905 (15)	C13—C14	1.3774 (14)
C1—C6	1.3975 (13)	C13—H13A	0.929 (16)
C1—H1A	0.934 (14)	C14—H14A	0.960 (14)
C2—C3	1.3923 (15)	C15—H15A	1.031 (14)
C2—H2A	0.985 (16)	C15—H15B	0.992 (14)
C3—C4	1.4029 (14)	C15—H15C	0.990 (16)
C4—C5	1.3819 (14)	C16—H16A	0.996 (16)
C4—H4A	0.944 (15)	C16—H16B	0.982 (16)
C5—C6	1.3992 (14)	C16—H16C	0.999 (17)
C5—H5A	0.943 (14)

C8—O1—C7	102.83 (7)	C10—C9—C8	121.21 (8)
C3—O2—C15	117.56 (9)	C14—C9—C8	119.66 (8)
C12—O3—C16	117.39 (8)	C9—C10—C11	120.82 (8)
C7—N1—N2	106.41 (8)	C9—C10—H10A	122.1 (8)
C8—N2—N1	106.13 (8)	C11—C10—H10A	117.1 (8)
C2—C1—C6	120.85 (9)	C10—C11—C12	119.35 (9)
C2—C1—H1A	119.5 (9)	C10—C11—H11A	118.0 (9)
C6—C1—H1A	119.6 (9)	C12—C11—H11A	122.5 (9)
C1—C2—C3	119.80 (9)	O3—C12—C11	124.75 (9)
C1—C2—H2A	118.4 (9)	O3—C12—C13	115.05 (8)
C3—C2—H2A	121.8 (9)	C11—C12—C13	120.20 (9)
O2—C3—C2	125.20 (9)	C14—C13—C12	119.87 (9)
O2—C3—C4	115.14 (9)	C14—C13—H13A	120.6 (10)
C2—C3—C4	119.66 (9)	C12—C13—H13A	119.5 (10)
C5—C4—C3	120.21 (10)	C13—C14—C9	120.66 (9)
C5—C4—H4A	121.6 (9)	C13—C14—H14A	119.5 (8)
C3—C4—H4A	118.2 (9)	C9—C14—H14A	119.8 (8)
C4—C5—C6	120.55 (9)	O2—C15—H15A	112.1 (8)
C4—C5—H5A	117.9 (9)	O2—C15—H15B	110.8 (8)
C6—C5—H5A	121.6 (9)	H15A—C15—H15B	110.0 (11)
C1—C6—C5	118.92 (9)	O2—C15—H15C	104.8 (10)
C1—C6—C7	120.62 (9)	H15A—C15—H15C	110.8 (12)
C5—C6—C7	120.46 (8)	H15B—C15—H15C	108.1 (12)
N1—C7—O1	112.27 (9)	O3—C16—H16A	110.8 (9)
N1—C7—C6	129.63 (9)	O3—C16—H16B	110.5 (9)
O1—C7—C6	118.09 (8)	H16A—C16—H16B	111.3 (13)
N2—C8—O1	112.35 (8)	O3—C16—H16C	104.4 (10)
N2—C8—C9	128.77 (9)	H16A—C16—H16C	109.8 (13)
O1—C8—C9	118.84 (8)	H16B—C16—H16C	109.8 (13)
C10—C9—C14	119.09 (9)

C7—N1—N2—C8	−0.41 (11)	N1—N2—C8—O1	0.33 (11)
C6—C1—C2—C3	0.44 (16)	N1—N2—C8—C9	−177.28 (9)
C15—O2—C3—C2	9.99 (16)	C7—O1—C8—N2	−0.13 (10)
C15—O2—C3—C4	−170.60 (10)	C7—O1—C8—C9	177.74 (8)
C1—C2—C3—O2	178.82 (10)	N2—C8—C9—C10	−175.90 (10)
C1—C2—C3—C4	−0.55 (16)	O1—C8—C9—C10	6.62 (13)
O2—C3—C4—C5	−179.38 (10)	N2—C8—C9—C14	6.42 (16)
C2—C3—C4—C5	0.05 (16)	O1—C8—C9—C14	−171.05 (8)
C3—C4—C5—C6	0.57 (16)	C14—C9—C10—C11	−0.04 (14)
C2—C1—C6—C5	0.18 (15)	C8—C9—C10—C11	−177.72 (9)
C2—C1—C6—C7	179.80 (9)	C9—C10—C11—C12	0.20 (14)
C4—C5—C6—C1	−0.69 (15)	C16—O3—C12—C11	2.71 (14)
C4—C5—C6—C7	179.69 (9)	C16—O3—C12—C13	−177.29 (9)
N2—N1—C7—O1	0.35 (11)	C10—C11—C12—O3	−179.73 (8)
N2—N1—C7—C6	−178.82 (9)	C10—C11—C12—C13	0.27 (14)
C8—O1—C7—N1	−0.15 (10)	O3—C12—C13—C14	179.08 (9)
C8—O1—C7—C6	179.12 (8)	C11—C12—C13—C14	−0.92 (15)
C1—C6—C7—N1	−11.61 (16)	C12—C13—C14—C9	1.10 (15)
C5—C6—C7—N1	168.01 (10)	C10—C9—C14—C13	−0.62 (14)
C1—C6—C7—O1	169.27 (9)	C8—C9—C14—C13	177.10 (9)
C5—C6—C7—O1	−11.12 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of C9–C14 and C1–C6 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cg1ⁱ	1.031 (14)	2.563 (16)	3.4903 (14)	149.4 (10)
C15—H15B···Cg2ⁱⁱ	0.992 (14)	2.994 (16)	3.8804 (14)	149.4 (11)

Symmetry codes: (i) x−1, y, z−1; (ii) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₃
M_r	282.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.7525 (2), 11.8973 (2), 11.6340 (2)
β (°)	115.434 (1)
V (Å³)	1344.04 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.53 × 0.49 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.950, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	17061, 4744, 3744
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.751

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.137, 1.03
No. of reflections	4744
No. of parameters	246
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.30

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of C9–C14 and C1–C6 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cg1ⁱ	1.031 (14)	2.563 (16)	3.4903 (14)	149.4 (10)
C15—H15B···Cg2ⁱⁱ	0.992 (14)	2.994 (16)	3.8804 (14)	149.4 (11)

Symmetry codes: (i) x−1, y, z−1; (ii) x, −y−1/2, z−3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160).

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