2-Isobutyl-6-phenyl­imidazo[2,1-b][1,3,4]thia­diazole

Fun, H.-K.; Hemamalini, M.; Prasad, D.J.; Castelino, P.A.; Anitha, V.V.

doi:10.1107/S1600536810053201

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o254

doi:10.1107/S1600536810053201

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2-Isobutyl-6-phenylimidazo[2,1-b][1,3,4]thiadiazole

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a D. Jagadeesh Prasad,^b Prakash Anil Castelino ^c and V. V. Anitha ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Mangalore University, Mangalore, Karnataka, India, and ^cDepartment of Chemistry, St. Philomena's College, Puttur, Dakshina Kannada, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 December 2010; accepted 18 December 2010; online 8 January 2011)

In the title compound, C₁₄H₁₅N₃S, the imidazo[2,1-b][1,3,4]thiadiazole fused-ring system is close to planar, with a maximum deviation of 0.042 (1) Å, and the dihedral angle between it and the phenyl ring is 24.21 (6)°. The isobutyl group is disordered over two sets of sites in a 0.899 (9):0.101 (9) ratio. In the crystal, weak aromatic π–π stacking interactions involving the imidazole and thiadiazole rings with a centroid–centroid distance of 3.8067 (7) Å occur.

Related literature

For applications of imidazo [2,1-b]-1,3,4-thiadiazole derivatives, see: Terzioglu & Gursoy (2003 ); Kolavi et al. (2006 ); Gadad et al. (2000 ); Andotra et al. (1997 ); Khazi et al. (1996 ); Andreani et al. (1982 , 1987 , 1991 ); Eberle & Robert (1977 ).

Experimental

Crystal data

C₁₄H₁₅N₃S
M_r = 257.35
Monoclinic, P 2₁ /n
a = 5.6921 (1) Å
b = 19.6453 (4) Å
c = 12.3610 (2) Å
β = 96.127 (1)°
V = 1374.35 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.65 × 0.48 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.870, T_max = 0.947
36499 measured reflections
4038 independent reflections
3378 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.115
S = 1.03
4038 reflections
191 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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/S1600536810053201/hb5776sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053201/hb5776Isup2.hkl

checkCIF report

Comment top

Imidazo [2,1-b]-1,3,4-thiadiazole derivatives are found to be biological active compounds possessing anticancer (Terzioglu & Gursoy, 2003), antitubercular (Kolavi et al., 2006), antibacterial (Gadad et al., 2000), antifungal (Andotra et al., 1997), anticonvulsant, analgesic (Khazi et al., 1996), anti-inflammatory (Andreani et al., 1982), diuretic (Andreani et al., 1991) and herbicidal activities (Andreani et al., 1991). Moreover 1,3,4-thiadiazoles have many interesting biological activities, for example, 2-amino-5-(trifluoromethylphenyl alkyl)-1,3,4 thidadiazoles were used in the treatment of insomnia and anxiety (Eberle & Robert, 1977).

The title compound is shown in Fig. 1. The imidazo[2,1-b] [1,3,4]thiadiazole (S1/N1–N3/C7–C10) ring is essentially planar, with a maximum deviation of 0.042 (1) Å for atom C7. The isobutyl group is disordered over two sets of positions, with a refined occupancy ratio of 0.899 (9):0.101 (9). The dihedral angle between the imidazo[2,1-b] [1,3,4]thiadiazole (S1/N1–N3/C7–C10) ring and the benzene ring (C1–C6) is 24.21 (6)°.

In the crystal structure (Fig. 2), there are no classical hydrogen bonds and stabilization is achieved by weak π–π stacking interactions between the thiadiazole (S1/N2–N3/C8–C9) ring and imidazole (N1–N2/C7–C8/C10) ring with centroid-to-centroid distance of 3.8067 (7) Å [symmetry code: 2-x, -y, 2-z].

Related literature top

For applications of imidazo [2,1-b]-1,3,4-thiadiazole derivatives, see: Terzioglu & Gursoy (2003); Kolavi et al. (2006); Gadad et al. (2000); Andotra et al. (1997); Khazi et al. (1996); Andreani et al. (1982, 1987, 1991); Eberle & Robert (1977).

Experimental top

5-isobutyl-1,3,4-thiadiazole-2-amine (1 molar equivalent) and phenacyl bromide (1 molar equivalent) are refluxed with ethanol for 4 hrs. The solvent was then distilled off and the reaction mass was poured into the crushed ice. The resulting solid, 2-isobutylimidazo[2,1-b][1,3,4]thiadiazole, that separated out was filtered and dried. The compound was recrystallized using ethanol and DMF mixture to form yellow blocks of the title compound. M.pt. 121–126°C.

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. Open bonds represent minor disorder components [H atoms are omitted for clarity].
	Fig. 2. The crystal packing of the title compound (I).

2-Isobutyl-6-phenylimidazo[2,1-b][1,3,4]thiadiazole top

Crystal data top

C₁₄H₁₅N₃S	F(000) = 544
M_r = 257.35	D_x = 1.244 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9875 reflections
a = 5.6921 (1) Å	θ = 2.7–30.3°
b = 19.6453 (4) Å	µ = 0.22 mm⁻¹
c = 12.3610 (2) Å	T = 296 K
β = 96.127 (1)°	Block, yellow
V = 1374.35 (4) Å³	0.65 × 0.48 × 0.25 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4038 independent reflections
Radiation source: fine-focus sealed tube	3378 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.870, T_max = 0.947	k = −27→27
36499 measured reflections	l = −17→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0607P)² + 0.2698P] where P = (F_o² + 2F_c²)/3
4038 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.31 e Å⁻³
3 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₁₅N₃S	V = 1374.35 (4) Å³
M_r = 257.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.6921 (1) Å	µ = 0.22 mm⁻¹
b = 19.6453 (4) Å	T = 296 K
c = 12.3610 (2) Å	0.65 × 0.48 × 0.25 mm
β = 96.127 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4038 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3378 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.947	R_int = 0.028
36499 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	3 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
4038 reflections	Δρ_min = −0.30 e Å⁻³
191 parameters

Special details top

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	Occ. (<1)
S1	−0.10652 (5)	0.001167 (15)	0.83286 (3)	0.04296 (11)
N1	−0.09710 (16)	0.12234 (5)	0.96090 (8)	0.0375 (2)
N2	0.23227 (16)	0.07221 (5)	0.91884 (8)	0.0369 (2)
N3	0.34801 (18)	0.02027 (5)	0.87202 (9)	0.0412 (2)
C1	−0.1245 (2)	0.25685 (7)	1.06391 (14)	0.0544 (3)
H1A	−0.2492	0.2450	1.0125	0.065*
C2	−0.1425 (3)	0.31387 (9)	1.12942 (17)	0.0724 (5)
H2A	−0.2792	0.3401	1.1213	0.087*
C3	0.0404 (3)	0.33173 (9)	1.20606 (16)	0.0731 (5)
H3A	0.0269	0.3697	1.2498	0.088*
C4	0.2424 (3)	0.29331 (9)	1.21764 (14)	0.0688 (4)
H4A	0.3664	0.3055	1.2691	0.083*
C5	0.2629 (3)	0.23646 (8)	1.15317 (12)	0.0540 (3)
H5A	0.4005	0.2106	1.1620	0.065*
C6	0.0797 (2)	0.21756 (6)	1.07525 (10)	0.0395 (2)
C7	0.10261 (19)	0.15721 (6)	1.00717 (9)	0.0361 (2)
C8	−0.00847 (18)	0.07150 (6)	0.90932 (9)	0.0346 (2)
C9	0.1913 (2)	−0.02035 (6)	0.82471 (10)	0.0387 (2)
C10	0.3078 (2)	0.12707 (6)	0.98180 (10)	0.0406 (3)
H10A	0.4625	0.1408	1.0026	0.049*
C11	0.2544 (2)	−0.08474 (6)	0.77025 (11)	0.0456 (3)
H11A	0.1916	−0.1229	0.8079	0.055*	0.899 (9)
H11B	0.4251	−0.0891	0.7778	0.055*	0.899 (9)
H11C	0.1818	−0.1211	0.8065	0.055*	0.101 (9)
H11D	0.4220	−0.0903	0.7866	0.055*	0.101 (9)
C12	0.1633 (7)	−0.08944 (18)	0.6491 (3)	0.0618 (9)	0.899 (9)
H12A	−0.0066	−0.0798	0.6399	0.074*	0.899 (9)
C13	0.2898 (12)	−0.03784 (19)	0.5858 (3)	0.1205 (16)	0.899 (9)
H13A	0.2567	0.0071	0.6105	0.181*	0.899 (9)
H13B	0.2362	−0.0418	0.5098	0.181*	0.899 (9)
H13C	0.4569	−0.0460	0.5970	0.181*	0.899 (9)
C14	0.2053 (8)	−0.16347 (16)	0.6126 (3)	0.0948 (11)	0.899 (9)
H14A	0.1100	−0.1940	0.6500	0.142*	0.899 (9)
H14B	0.3690	−0.1750	0.6295	0.142*	0.899 (9)
H14C	0.1629	−0.1673	0.5355	0.142*	0.899 (9)
C12A	0.205 (7)	−0.0960 (19)	0.666 (2)	0.081 (12)	0.101 (9)
H12B	0.0650	−0.1245	0.6708	0.097*	0.101 (9)
C13A	0.096 (9)	−0.0463 (17)	0.583 (3)	0.122 (14)	0.101 (9)
H13D	0.0313	−0.0705	0.5196	0.182*	0.101 (9)
H13E	0.2154	−0.0152	0.5641	0.182*	0.101 (9)
H13F	−0.0266	−0.0214	0.6131	0.182*	0.101 (9)
C14A	0.347 (8)	−0.147 (2)	0.601 (2)	0.119 (13)	0.101 (9)
H14D	0.2895	−0.1445	0.5251	0.179*	0.101 (9)
H14E	0.3267	−0.1923	0.6271	0.179*	0.101 (9)
H14F	0.5114	−0.1350	0.6105	0.179*	0.101 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03290 (16)	0.04292 (18)	0.0523 (2)	0.00072 (10)	0.00121 (12)	−0.00946 (12)
N1	0.0321 (4)	0.0376 (5)	0.0430 (5)	0.0029 (4)	0.0052 (4)	−0.0013 (4)
N2	0.0301 (4)	0.0383 (5)	0.0433 (5)	0.0006 (3)	0.0085 (3)	−0.0043 (4)
N3	0.0344 (5)	0.0421 (5)	0.0484 (6)	0.0028 (4)	0.0112 (4)	−0.0066 (4)
C1	0.0432 (7)	0.0453 (7)	0.0753 (9)	0.0023 (5)	0.0096 (6)	−0.0114 (6)
C2	0.0595 (9)	0.0530 (8)	0.1081 (14)	0.0077 (7)	0.0254 (9)	−0.0217 (9)
C3	0.0771 (11)	0.0602 (9)	0.0865 (12)	−0.0070 (8)	0.0290 (9)	−0.0330 (9)
C4	0.0735 (11)	0.0698 (10)	0.0628 (9)	−0.0057 (8)	0.0062 (8)	−0.0265 (8)
C5	0.0543 (8)	0.0548 (8)	0.0522 (7)	0.0028 (6)	0.0029 (6)	−0.0118 (6)
C6	0.0416 (6)	0.0358 (5)	0.0426 (6)	−0.0016 (4)	0.0116 (5)	−0.0015 (4)
C7	0.0354 (5)	0.0351 (5)	0.0383 (5)	−0.0004 (4)	0.0068 (4)	0.0000 (4)
C8	0.0297 (5)	0.0364 (5)	0.0378 (5)	0.0012 (4)	0.0038 (4)	0.0004 (4)
C9	0.0371 (5)	0.0393 (5)	0.0403 (6)	0.0034 (4)	0.0077 (4)	−0.0009 (4)
C10	0.0328 (5)	0.0413 (6)	0.0482 (6)	−0.0040 (4)	0.0071 (4)	−0.0070 (5)
C11	0.0472 (6)	0.0403 (6)	0.0503 (7)	0.0036 (5)	0.0107 (5)	−0.0065 (5)
C12	0.0621 (18)	0.0715 (19)	0.0501 (12)	0.0138 (12)	−0.0009 (11)	−0.0205 (13)
C13	0.182 (5)	0.123 (3)	0.0616 (15)	−0.005 (3)	0.037 (2)	0.0168 (16)
C14	0.104 (2)	0.0893 (19)	0.0898 (18)	0.0083 (16)	0.0063 (16)	−0.0506 (15)
C12A	0.049 (13)	0.082 (17)	0.11 (3)	0.033 (11)	−0.001 (12)	0.044 (17)
C13A	0.15 (4)	0.12 (3)	0.088 (19)	−0.01 (2)	0.00 (2)	−0.037 (19)
C14A	0.15 (3)	0.14 (3)	0.070 (14)	−0.02 (2)	0.020 (18)	−0.055 (16)

Geometric parameters (Å, º) top

S1—C8	1.7324 (11)	C11—C12	1.534 (3)
S1—C9	1.7605 (12)	C11—H11A	0.9700
N1—C8	1.3142 (14)	C11—H11B	0.9700
N1—C7	1.3963 (15)	C11—H11C	0.9600
N2—C8	1.3629 (14)	C11—H11D	0.9600
N2—C10	1.3714 (15)	C12—C13	1.509 (5)
N2—N3	1.3753 (13)	C12—C14	1.549 (4)
N3—C9	1.2895 (16)	C12—H12A	0.9800
C1—C6	1.3894 (18)	C13—H13A	0.9600
C1—C2	1.392 (2)	C13—H13B	0.9600
C1—H1A	0.9300	C13—H13C	0.9600
C2—C3	1.376 (3)	C14—H14A	0.9600
C2—H2A	0.9300	C14—H14B	0.9600
C3—C4	1.370 (3)	C14—H14C	0.9600
C3—H3A	0.9300	C12A—C13A	1.501 (18)
C4—C5	1.384 (2)	C12A—C14A	1.563 (18)
C4—H4A	0.9300	C12A—H12B	0.9800
C5—C6	1.3925 (19)	C13A—H13D	0.9600
C5—H5A	0.9300	C13A—H13E	0.9600
C6—C7	1.4678 (16)	C13A—H13F	0.9600
C7—C10	1.3753 (15)	C14A—H14D	0.9600
C9—C11	1.4946 (16)	C14A—H14E	0.9600
C10—H10A	0.9300	C14A—H14F	0.9600
C11—C12A	1.30 (3)

C8—S1—C9	88.09 (5)	C12A—C11—H11C	106.0
C8—N1—C7	103.51 (9)	C9—C11—H11C	106.5
C8—N2—C10	107.97 (9)	C12—C11—H11C	107.0
C8—N2—N3	118.59 (9)	H11B—C11—H11C	111.4
C10—N2—N3	133.36 (10)	C12A—C11—H11D	107.0
C9—N3—N2	108.10 (9)	C9—C11—H11D	106.5
C6—C1—C2	120.06 (15)	C12—C11—H11D	115.0
C6—C1—H1A	120.0	H11A—C11—H11D	102.7
C2—C1—H1A	120.0	H11C—C11—H11D	106.5
C3—C2—C1	120.55 (16)	C13—C12—C11	109.6 (3)
C3—C2—H2A	119.7	C13—C12—C14	112.5 (3)
C1—C2—H2A	119.7	C11—C12—C14	107.1 (3)
C4—C3—C2	119.75 (15)	C13—C12—H12A	109.2
C4—C3—H3A	120.1	C11—C12—H12A	109.2
C2—C3—H3A	120.1	C14—C12—H12A	109.2
C3—C4—C5	120.38 (16)	C12—C13—H13A	109.5
C3—C4—H4A	119.8	C12—C13—H13B	109.5
C5—C4—H4A	119.8	H13A—C13—H13B	109.5
C4—C5—C6	120.69 (14)	C12—C13—H13C	109.5
C4—C5—H5A	119.7	H13A—C13—H13C	109.5
C6—C5—H5A	119.7	H13B—C13—H13C	109.5
C1—C6—C5	118.57 (12)	C12—C14—H14A	109.5
C1—C6—C7	121.03 (12)	C12—C14—H14B	109.5
C5—C6—C7	120.40 (11)	H14A—C14—H14B	109.5
C10—C7—N1	111.69 (10)	C12—C14—H14C	109.5
C10—C7—C6	127.46 (11)	H14A—C14—H14C	109.5
N1—C7—C6	120.84 (10)	H14B—C14—H14C	109.5
N1—C8—N2	112.63 (10)	C11—C12A—C13A	126 (2)
N1—C8—S1	138.83 (9)	C11—C12A—C14A	123 (2)
N2—C8—S1	108.52 (8)	C13A—C12A—C14A	105 (2)
N3—C9—C11	122.70 (11)	C11—C12A—H12B	97.6
N3—C9—S1	116.69 (9)	C13A—C12A—H12B	97.6
C11—C9—S1	120.53 (9)	C14A—C12A—H12B	97.6
N2—C10—C7	104.19 (10)	C12A—C13A—H13D	109.5
N2—C10—H10A	127.9	C12A—C13A—H13E	109.5
C7—C10—H10A	127.9	H13D—C13A—H13E	109.5
C12A—C11—C9	123.4 (13)	C12A—C13A—H13F	109.5
C9—C11—C12	114.71 (15)	H13D—C13A—H13F	109.5
C12A—C11—H11A	106.9	H13E—C13A—H13F	109.5
C9—C11—H11A	108.6	C12A—C14A—H14D	109.5
C12—C11—H11A	108.6	C12A—C14A—H14E	109.5
C12A—C11—H11B	100.8	H14D—C14A—H14E	109.5
C9—C11—H11B	108.6	C12A—C14A—H14F	109.5
C12—C11—H11B	108.6	H14D—C14A—H14F	109.5
H11A—C11—H11B	107.6	H14E—C14A—H14F	109.5

C8—N2—N3—C9	0.80 (15)	C9—S1—C8—N1	−177.43 (13)
C10—N2—N3—C9	177.01 (12)	C9—S1—C8—N2	1.10 (9)
C6—C1—C2—C3	−0.3 (3)	N2—N3—C9—C11	−176.63 (11)
C1—C2—C3—C4	0.3 (3)	N2—N3—C9—S1	0.17 (13)
C2—C3—C4—C5	−0.4 (3)	C8—S1—C9—N3	−0.77 (10)
C3—C4—C5—C6	0.3 (3)	C8—S1—C9—C11	176.10 (10)
C2—C1—C6—C5	0.2 (2)	C8—N2—C10—C7	−0.12 (13)
C2—C1—C6—C7	179.96 (14)	N3—N2—C10—C7	−176.62 (12)
C4—C5—C6—C1	−0.2 (2)	N1—C7—C10—N2	−0.26 (13)
C4—C5—C6—C7	−179.99 (13)	C6—C7—C10—N2	178.61 (11)
C8—N1—C7—C10	0.54 (13)	N3—C9—C11—C12A	−117 (2)
C8—N1—C7—C6	−178.42 (10)	S1—C9—C11—C12A	66 (2)
C1—C6—C7—C10	156.55 (13)	N3—C9—C11—C12	−121.5 (2)
C5—C6—C7—C10	−23.69 (19)	S1—C9—C11—C12	61.8 (2)
C1—C6—C7—N1	−24.67 (17)	C12A—C11—C12—C13	−89 (14)
C5—C6—C7—N1	155.09 (12)	C9—C11—C12—C13	67.7 (4)
C7—N1—C8—N2	−0.62 (13)	C12A—C11—C12—C14	33 (13)
C7—N1—C8—S1	177.88 (11)	C9—C11—C12—C14	−170.0 (2)
C10—N2—C8—N1	0.49 (13)	C9—C11—C12A—C13A	5 (6)
N3—N2—C8—N1	177.59 (10)	C12—C11—C12A—C13A	30 (10)
C10—N2—C8—S1	−178.47 (8)	C9—C11—C12A—C14A	155 (3)
N3—N2—C8—S1	−1.36 (13)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₃S
M_r	257.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.6921 (1), 19.6453 (4), 12.3610 (2)
β (°)	96.127 (1)
V (Å³)	1374.35 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.65 × 0.48 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.870, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	36499, 4038, 3378
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.115, 1.03
No. of reflections	4038
No. of parameters	191
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.30

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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