1-[2-(4-Chloro­phen­yl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone

Fun, H.-K.; Arshad, S.; Shyma, P.C.; Kalluraya, B.; Arulmoli, T.

doi:10.1107/S1600536812023100

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1901

doi:10.1107/S1600536812023100

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1-[2-(4-Chlorophenyl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a P. C. Shyma,^b Balakrishna Kalluraya ^b and T. Arulmoli ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangothri 574 199, Karnataka, India, and ^cSeQuent Scientific Limited, No: 120 A & B, Industrial Area, Baikampady, New Mangalore, Karnataka 575 011, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 May 2012; accepted 21 May 2012; online 26 May 2012)

In the title compound, C₁₆H₁₄ClN₃O₂, the 2,3-dihydro-1,3,4-oxadiazole ring [maximum deviation = 0.030 (1) Å] and the pyridine ring [maximum deviation = 0.012 (1) Å] are inclined slightly to one another, making a dihedral angle of 11.91 (5)°. The chloro-substituted phenyl ring is almost perpendicular to the 2,3-dihydro-1,3,4-oxadiazole and pyridine rings at dihedral angles of 86.86 (5) and 75.26 (5)°, respectively. In the crystal, π–π [centroid–centroid distance = 3.7311 (6) Å] and C—H⋯π interactions are observed.

Related literature

For the biological activity of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoline ring systems, see: Rakesh & Prabhakar (2009 ); Priya et al. (2007 ); Bhatia & Gupta (2011 ); Vijesh et al. (2011 ); Galil & Amr (2000 ). For related structures, see: Yehye et al. (2010 ); Ono et al. (2009 ). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₄ClN₃O₂
M_r = 315.75
Triclinic, $[P \overline 1]$
a = 5.8623 (2) Å
b = 10.9912 (5) Å
c = 12.2815 (5) Å
α = 68.214 (1)°
β = 84.707 (1)°
γ = 87.623 (1)°
V = 731.67 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.40 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.899, T_max = 0.962
19562 measured reflections
5301 independent reflections
4768 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.116
S = 1.02
5301 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯Cg3ⁱ	0.98	2.65	3.4360 (13)	138
Symmetry code: (i) -x+1, -y+2, -z+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: 10.1107/S1600536812023100/hb6803sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023100/hb6803Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023100/hb6803Isup3.cml

checkCIF report

Comment top

Oxadiazole, a five-membered heterocyclic nucleus, has attracted a wide attention of the chemists in search for the new therapeutic molecules. A number of therapeutic agents such as HIV-integrase inhibitor Raltegravir, a nitrofuran antibacterial Furamizole, antihypertensive agents like Tiodazosin and Nesapidil are based on the 1,3,4-oxadiazole moiety. The 3-acetyl-2,5-disubstituted-2,3- dihydro-1,3,4-oxadiazoline ring systems are associated with diverse biological properties such as analgesic, anti-inflammatory, anticancer, anti-HIV, antibacterial, antitubercular activities (Rakesh & Prabhakar, 2009; Priya et al., 2007; Bhatia & Gupta, 2011). Further, substituted pyridines have showed significant biological activities (Vijesh et al., 2011; Galil & Amr, 2000). Pyridine-derived pharmaceuticals include Atazanavir and Imatinib mesylate which are recommended for the treatment of HIV and chronic myelogenous leukemia respectively. Keeping in view of the therapeutic importance of 1,3,4-oxadiazoles and pyridines, we synthesized the title compound to study its crystal structure.

In the molecular structure (Fig. 1), the 2,3-dihydro-1,3,4-oxadiazole ring [O1/N2/N3/C6/C7, with a maximum deviation of 0.030 (1) Å at atom C7] and the pyridine ring [N1/C1–C5, with a maximum deviation of 0.012 (1) Å at atom C3 and C5] are slightly inclined to one another, making a dihedral angle of 11.91 (5)°. Meanwhile, the chloro-substituted phenyl ring (C8–C13) is almost perpendicular to the 2,3-dihydro-1,3,4-oxadiazole and pyridine rings at dihedral angles of 86.86 (5) and 75.26 (5)°, respectively. Bond lengths and angles are within normal ranges and are comparable to related structures (Yehye et al., 2010; Ono et al., 2009).

The crystal packing is shown in Fig. 2. π–π interactions are observed with centroid to centroid distance Cg1···Cg2 = 3.7311 (6) Å; symmetry code: 1 - x, 2 - y,1 - z. The crystal structure also features intermolecular C16—H16A···Cg3 (Table 1) interactions (Cg1, Cg2 and Cg3 are the centroids of O1/N2/N3/C6/C7, N1/C1–C5 and C8–C13 rings, respectively).

Related literature top

For the biological activity of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoline ring systems, see: Rakesh & Prabhakar (2009); Priya et al. (2007); Bhatia & Gupta (2011); Vijesh et al. (2011); Galil & Amr (2000). For related structures, see: Yehye et al. (2010); Ono et al. (2009). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Schiff base, N'-[(1E)-(4-chlorophenyl)methylene]-4- methylbenzohydrazide (0.5 g, 0.0018 mol) was refluxed with acetic anhydride (3 ml) for 1 h. After the completion of reaction, the excess acetic anhydride was distilled out at reduced pressure and the residue obtained was poured into ice cold water. The solid that was separated out was filtered, washed with water and dried. The crude product was recrystallized from hot ethanol in the form of yellow blocks (0.38 g, 76%). M.p.: 395–397 K.

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.
	Fig. 2. A packing diagram of the title compound viewed along the a axis.

1-[2-(4-Chlorophenyl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone top

Crystal data top

C₁₆H₁₄ClN₃O₂	Z = 2
M_r = 315.75	F(000) = 328
Triclinic, P1	D_x = 1.433 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8623 (2) Å	Cell parameters from 9976 reflections
b = 10.9912 (5) Å	θ = 3.1–32.6°
c = 12.2815 (5) Å	µ = 0.27 mm⁻¹
α = 68.214 (1)°	T = 100 K
β = 84.707 (1)°	Block, yellow
γ = 87.623 (1)°	0.40 × 0.22 × 0.14 mm
V = 731.67 (5) Å³

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	5301 independent reflections
Radiation source: fine-focus sealed tube	4768 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 32.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.899, T_max = 0.962	k = −16→16
19562 measured reflections	l = −18→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0681P)² + 0.3111P] where P = (F_o² + 2F_c²)/3
5301 reflections	(Δ/σ)_max = 0.003
195 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₁₆H₁₄ClN₃O₂	γ = 87.623 (1)°
M_r = 315.75	V = 731.67 (5) Å³
Triclinic, P1	Z = 2
a = 5.8623 (2) Å	Mo Kα radiation
b = 10.9912 (5) Å	µ = 0.27 mm⁻¹
c = 12.2815 (5) Å	T = 100 K
α = 68.214 (1)°	0.40 × 0.22 × 0.14 mm
β = 84.707 (1)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	5301 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4768 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.962	R_int = 0.021
19562 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	Δρ_max = 0.60 e Å⁻³
5301 reflections	Δρ_min = −0.64 e Å⁻³
195 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 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
Cl1	0.93968 (5)	0.44230 (2)	1.24269 (2)	0.02345 (8)
O1	0.75357 (12)	0.84198 (7)	0.70235 (6)	0.01543 (13)
O2	0.71195 (14)	1.07742 (8)	0.89561 (7)	0.02114 (16)
N1	0.14662 (17)	0.82200 (10)	0.47108 (8)	0.02164 (14)
N2	0.42483 (14)	0.94931 (8)	0.72117 (7)	0.01425 (14)
N3	0.57912 (14)	0.96760 (8)	0.79406 (7)	0.01478 (15)
C1	0.56078 (19)	0.72732 (11)	0.56195 (10)	0.0218 (2)
H1A	0.7044	0.6960	0.5920	0.026*
C2	0.4694 (2)	0.67544 (11)	0.49036 (10)	0.0221 (2)
H2A	0.5479	0.6079	0.4709	0.026*
C3	0.26192 (19)	0.72257 (11)	0.44693 (9)	0.02164 (14)
C4	0.23766 (16)	0.87227 (10)	0.54253 (9)	0.01640 (17)
H4A	0.1587	0.9408	0.5601	0.020*
C5	0.44533 (16)	0.82564 (9)	0.59111 (8)	0.01382 (16)
C6	0.53469 (15)	0.87669 (9)	0.67240 (8)	0.01324 (15)
C7	0.79357 (15)	0.89356 (9)	0.79165 (8)	0.01384 (16)
H7A	0.9281	0.9536	0.7659	0.017*
C8	0.82979 (15)	0.78264 (9)	0.90601 (8)	0.01289 (15)
C9	1.02946 (15)	0.77444 (10)	0.96167 (8)	0.01520 (16)
H9A	1.1425	0.8404	0.9281	0.018*
C10	1.06480 (16)	0.67008 (10)	1.06622 (9)	0.01629 (17)
H10A	1.2006	0.6646	1.1045	0.020*
C11	0.89815 (16)	0.57433 (9)	1.11339 (8)	0.01493 (16)
C12	0.69506 (17)	0.58158 (10)	1.06022 (9)	0.01712 (17)
H12A	0.5814	0.5160	1.0944	0.021*
C13	0.66228 (16)	0.68659 (10)	0.95626 (9)	0.01628 (17)
H13A	0.5248	0.6931	0.9191	0.020*
C14	0.1547 (3)	0.66352 (15)	0.37211 (12)	0.0388 (3)
H14A	0.0095	0.6224	0.4122	0.058*
H14B	0.2585	0.5973	0.3588	0.058*
H14C	0.1261	0.7322	0.2964	0.058*
C15	0.55511 (17)	1.06142 (9)	0.84241 (8)	0.01540 (16)
C16	0.33496 (18)	1.13830 (10)	0.82619 (10)	0.02050 (19)
H16A	0.3508	1.2156	0.8465	0.031*
H16B	0.2109	1.0833	0.8775	0.031*
H16C	0.2994	1.1662	0.7440	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02985 (14)	0.01791 (12)	0.01908 (12)	0.00100 (9)	−0.00754 (9)	−0.00162 (9)
O1	0.0136 (3)	0.0209 (3)	0.0149 (3)	0.0038 (2)	−0.0041 (2)	−0.0101 (3)
O2	0.0226 (3)	0.0219 (4)	0.0229 (4)	−0.0025 (3)	−0.0045 (3)	−0.0119 (3)
N1	0.0243 (3)	0.0241 (3)	0.0164 (3)	−0.0039 (2)	−0.0053 (2)	−0.0062 (2)
N2	0.0145 (3)	0.0157 (3)	0.0139 (3)	0.0009 (3)	−0.0034 (2)	−0.0065 (3)
N3	0.0151 (3)	0.0162 (3)	0.0158 (3)	0.0032 (3)	−0.0046 (3)	−0.0087 (3)
C1	0.0233 (5)	0.0244 (5)	0.0237 (5)	0.0070 (4)	−0.0089 (4)	−0.0151 (4)
C2	0.0275 (5)	0.0232 (5)	0.0224 (5)	0.0061 (4)	−0.0094 (4)	−0.0153 (4)
C3	0.0243 (3)	0.0241 (3)	0.0164 (3)	−0.0039 (2)	−0.0053 (2)	−0.0062 (2)
C4	0.0162 (4)	0.0185 (4)	0.0146 (4)	0.0005 (3)	−0.0031 (3)	−0.0059 (3)
C5	0.0153 (4)	0.0147 (4)	0.0117 (4)	−0.0003 (3)	−0.0019 (3)	−0.0051 (3)
C6	0.0127 (3)	0.0143 (4)	0.0121 (4)	0.0008 (3)	−0.0021 (3)	−0.0040 (3)
C7	0.0133 (3)	0.0160 (4)	0.0136 (4)	0.0010 (3)	−0.0027 (3)	−0.0068 (3)
C8	0.0123 (3)	0.0144 (4)	0.0133 (4)	0.0008 (3)	−0.0023 (3)	−0.0066 (3)
C9	0.0121 (3)	0.0190 (4)	0.0151 (4)	−0.0012 (3)	−0.0017 (3)	−0.0067 (3)
C10	0.0133 (4)	0.0200 (4)	0.0159 (4)	0.0006 (3)	−0.0034 (3)	−0.0065 (3)
C11	0.0174 (4)	0.0140 (4)	0.0141 (4)	0.0022 (3)	−0.0030 (3)	−0.0058 (3)
C12	0.0183 (4)	0.0147 (4)	0.0186 (4)	−0.0027 (3)	−0.0037 (3)	−0.0057 (3)
C13	0.0147 (4)	0.0166 (4)	0.0180 (4)	−0.0020 (3)	−0.0046 (3)	−0.0059 (3)
C14	0.0595 (9)	0.0387 (7)	0.0213 (5)	−0.0216 (7)	−0.0116 (5)	−0.0106 (5)
C15	0.0191 (4)	0.0131 (4)	0.0144 (4)	−0.0012 (3)	0.0001 (3)	−0.0059 (3)
C16	0.0223 (4)	0.0185 (4)	0.0235 (5)	0.0051 (3)	−0.0026 (4)	−0.0114 (4)

Geometric parameters (Å, º) top

Cl1—C11	1.7373 (10)	C7—C8	1.5055 (13)
O1—C6	1.3673 (11)	C7—H7A	1.0000
O1—C7	1.4489 (11)	C8—C9	1.3923 (12)
O2—C15	1.2300 (12)	C8—C13	1.3966 (13)
N1—C4	1.3531 (13)	C9—C10	1.3941 (14)
N1—C3	1.3716 (16)	C9—H9A	0.9500
N2—C6	1.2851 (12)	C10—C11	1.3878 (14)
N2—N3	1.3993 (11)	C10—H10A	0.9500
N3—C15	1.3648 (12)	C11—C12	1.3954 (13)
N3—C7	1.4730 (12)	C12—C13	1.3900 (14)
C1—C2	1.3674 (14)	C12—H12A	0.9500
C1—C5	1.3914 (14)	C13—H13A	0.9500
C1—H1A	0.9500	C14—H14A	0.9800
C2—C3	1.3764 (15)	C14—H14B	0.9800
C2—H2A	0.9500	C14—H14C	0.9800
C3—C14	1.4979 (16)	C15—C16	1.5005 (14)
C4—C5	1.3986 (13)	C16—H16A	0.9800
C4—H4A	0.9500	C16—H16B	0.9800
C5—C6	1.4569 (13)	C16—H16C	0.9800

C6—O1—C7	106.85 (7)	C13—C8—C7	119.68 (8)
C4—N1—C3	118.61 (9)	C8—C9—C10	120.49 (9)
C6—N2—N3	104.34 (8)	C8—C9—H9A	119.8
C15—N3—N2	124.21 (8)	C10—C9—H9A	119.8
C15—N3—C7	123.06 (8)	C11—C10—C9	118.84 (9)
N2—N3—C7	111.51 (7)	C11—C10—H10A	120.6
C2—C1—C5	120.58 (10)	C9—C10—H10A	120.6
C2—C1—H1A	119.7	C10—C11—C12	121.68 (9)
C5—C1—H1A	119.7	C10—C11—Cl1	119.71 (7)
C1—C2—C3	118.95 (10)	C12—C11—Cl1	118.60 (7)
C1—C2—H2A	120.5	C13—C12—C11	118.69 (9)
C3—C2—H2A	120.5	C13—C12—H12A	120.7
N1—C3—C2	122.02 (10)	C11—C12—H12A	120.7
N1—C3—C14	118.22 (11)	C12—C13—C8	120.56 (9)
C2—C3—C14	119.75 (12)	C12—C13—H13A	119.7
N1—C4—C5	121.54 (9)	C8—C13—H13A	119.7
N1—C4—H4A	119.2	C3—C14—H14A	109.5
C5—C4—H4A	119.2	C3—C14—H14B	109.5
C1—C5—C4	118.25 (9)	H14A—C14—H14B	109.5
C1—C5—C6	121.10 (9)	C3—C14—H14C	109.5
C4—C5—C6	120.63 (8)	H14A—C14—H14C	109.5
N2—C6—O1	116.52 (8)	H14B—C14—H14C	109.5
N2—C6—C5	126.02 (8)	O2—C15—N3	118.81 (9)
O1—C6—C5	117.44 (8)	O2—C15—C16	124.60 (9)
O1—C7—N3	100.48 (7)	N3—C15—C16	116.59 (9)
O1—C7—C8	109.92 (7)	C15—C16—H16A	109.5
N3—C7—C8	113.89 (8)	C15—C16—H16B	109.5
O1—C7—H7A	110.7	H16A—C16—H16B	109.5
N3—C7—H7A	110.7	C15—C16—H16C	109.5
C8—C7—H7A	110.7	H16A—C16—H16C	109.5
C9—C8—C13	119.71 (9)	H16B—C16—H16C	109.5
C9—C8—C7	120.61 (8)

C6—N2—N3—C15	164.62 (9)	C15—N3—C7—O1	−162.77 (8)
C6—N2—N3—C7	−3.06 (10)	N2—N3—C7—O1	5.08 (10)
C5—C1—C2—C3	0.40 (18)	C15—N3—C7—C8	79.78 (11)
C4—N1—C3—C2	−1.88 (16)	N2—N3—C7—C8	−112.37 (9)
C4—N1—C3—C14	177.33 (10)	O1—C7—C8—C9	123.04 (9)
C1—C2—C3—N1	1.52 (18)	N3—C7—C8—C9	−125.11 (9)
C1—C2—C3—C14	−177.68 (11)	O1—C7—C8—C13	−56.48 (11)
C3—N1—C4—C5	0.33 (15)	N3—C7—C8—C13	55.37 (11)
C2—C1—C5—C4	−1.86 (16)	C13—C8—C9—C10	0.93 (14)
C2—C1—C5—C6	176.61 (10)	C7—C8—C9—C10	−178.58 (8)
N1—C4—C5—C1	1.50 (15)	C8—C9—C10—C11	0.34 (14)
N1—C4—C5—C6	−176.97 (9)	C9—C10—C11—C12	−1.41 (15)
N3—N2—C6—O1	−0.56 (11)	C9—C10—C11—Cl1	179.25 (7)
N3—N2—C6—C5	177.71 (9)	C10—C11—C12—C13	1.16 (15)
C7—O1—C6—N2	3.92 (11)	Cl1—C11—C12—C13	−179.50 (8)
C7—O1—C6—C5	−174.50 (8)	C11—C12—C13—C8	0.16 (15)
C1—C5—C6—N2	−166.88 (10)	C9—C8—C13—C12	−1.19 (15)
C4—C5—C6—N2	11.55 (15)	C7—C8—C13—C12	178.33 (9)
C1—C5—C6—O1	11.37 (14)	N2—N3—C15—O2	−172.90 (9)
C4—C5—C6—O1	−170.20 (8)	C7—N3—C15—O2	−6.60 (14)
C6—O1—C7—N3	−5.07 (9)	N2—N3—C15—C16	7.16 (14)
C6—O1—C7—C8	115.27 (8)	C7—N3—C15—C16	173.46 (9)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···Cg3ⁱ	0.98	2.65	3.4360 (13)	138

Symmetry code: (i) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄ClN₃O₂
M_r	315.75
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.8623 (2), 10.9912 (5), 12.2815 (5)
α, β, γ (°)	68.214 (1), 84.707 (1), 87.623 (1)
V (Å³)	731.67 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.40 × 0.22 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.899, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	19562, 5301, 4768
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.116, 1.02
No. of reflections	5301
No. of parameters	195
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.64

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

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···Cg3ⁱ	0.98	2.65	3.4360 (13)	138

Symmetry code: (i) −x+1, −y+2, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA also thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award.

References

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