Crystal structure of 3-benzyl­sulfanyl-6-(5-methyl-1,2-oxazol-3-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Vaarla, K.; Rao, V.R.; Akkurt, M.

doi:10.1107/S2056989015017351

organic compounds

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ISSN: 2056-9890

Volume 71| Part 11| November 2015| Pages o809-o810

https://doi.org/10.1107/S2056989015017351

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Crystal structure of 3-benzylsulfanyl-6-(5-methyl-1,2-oxazol-3-yl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

Krishnaiah Vaarla,^a V. Rajeswar Rao ^a ^* and Mehmet Akkurt ^b

^aDepartment of Chemistry, National Institute of Technology, Warangal, Telangana 506004, India, and ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: rajeswarnitw@gmail.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 14 September 2015; accepted 17 September 2015; online 3 October 2015)

In the title compound, C₁₄H₁₁N₅OS₂, the triazolo–thiadiazole system is essentially planar (r.m.s. deviation = 0.002 Å) and makes dihedral angles of 6.33 (12) and 42.95 (14)° with the planes of the oxazole and phenyl rings, respectively. In the crystal, face-to-face π–π interactions are observed between the thiadiazole and oxazole rings [centroid–centroid distance = 3.4707 (18) Å], leading to columns along [010].

Keywords: crystal structure; triazolo–thiadiazole system; isoxazole ring.

CCDC reference: 1425251

1. Related literature

For the pharmocological properties of isoxazole, see: Kuz'min et al. (2007 ); Yermolina et al. (2011 ); Lilienkampf et al. (2010 ); Kamal et al. (2011 ). For the bioactivity of 1,2,4-triazoles coupled with the thiadiazole heterocylic ring system, see: Singh & Singh (2009 ). For biological applications, such as antimicrobial, anticancer, antiviral and antihelmentic properties, see: Habib et al. (1997 ); Bhat et al. (2004 ); Farghaly et al. (2006 ); Khalil et al. (1999 ). For the synthesis, see: Vaarla & Rao (2014 ). For a similar structure, see: Dinçer et al. (2005 ).

2. Experimental

2.1. Crystal data

C₁₄H₁₁N₅OS₂
M_r = 329.40
Orthorhombic, P c a 2₁
a = 16.271 (5) Å
b = 5.3804 (13) Å
c = 16.700 (4) Å
V = 1462.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 296 K
0.50 × 0.45 × 0.30 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.836, T_max = 0.896
10433 measured reflections
3117 independent reflections
2905 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.077
S = 1.08
3117 reflections
200 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 )
Absolute structure parameter: 0.02 (2)

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1425251

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015017351/tk5386sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015017351/tk5386Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015017351/tk5386Isup3.cml

checkCIF report

Comment top

Nitrogen heterocyclic compounds have received much attention among researchers throughout the world for their applications as biological probes in the field of drug discovery. Isoxazole is a five membered O- and N-containing heterocylic compound and widely used as key building pharmacophore for drugs (Kuz'min et al., 2007; Yermolina et al., 2011; Lilienkampf et al., 2010; Kamal et al., 2011). Isoxazoles have a wide range of biological applications such as antiviral, anticancer, antibiotic, antituberculosis, antiinflammatory and antimicrobial agents, and as COX-2 inhibitors (Singh & Singh, 2009).

A large number of [1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles have remarkable biological applications such as antimicrobial (Habib et al., 1997), anticancer (Bhat et al., 2004), antiviral (Farghaly et al., 2006) and antihelmentic (Khalil et al., 1999) properties.

The title molecule is shown in Fig. 1. The plane of the triazolo-thiadiazole system [r.m.s. deviation = 0.002 Å] forms dihedral angles of 6.33 (12) and 42.95 (14)° with the oxazole (O1/N1/C2–C4) and phenyl (C9–C14) rings, respectively. All the bond lengths and bond angles in the compound are within normal ranges and comparable with those reported in a similar compound (Dinçer et al., 2005).

The crystal structure is stabilized by face-to-face π—π interactions [Cg1···Cg2 (x, -1 + y, z) = 3.4707 (18) Å and Cg2···Cg1 (x, 1 + y, z) = 3.4707 (18) Å] between the ring centroids, Cg1 and Cg2, of the thiadiazole and oxazole rings, respectively. Fig. 2 shows the molecular packing of the title compound down the b axis.

Related literature top

For the pharmocological properties of isoxazole, see: Kuz'min et al. (2007); Yermolina et al. (2011); Lilienkampf et al. (2010); Kamal et al. (2011). For the bioactivity of 1,2,4-triazoles coupled with the thiadiazole heterocylic ring system, see: Singh & Singh (2009). For biological applications, such as antimicrobial, anticancer, antiviral and antihelmentic properties, see: Habib et al. (1997); Bhat et al. (2004); Farghaly et al. (2006); Khalil et al. (1999). For the synthesis, see: Vaarla & Rao (2014). For a similar structure, see: Dinçer et al. (2005).

Experimental top

The title compound was synthesized according to the published procedure (Vaarla & Rao, 2014). The compound was synthesized in two steps. In step one, a mixture containing equivalent amounts of 5-methylisoxazole-3-carboxylic acid and 4-amino-4H-[1,2,4]triazole-3,5-dithiol was refluxed in the presence of phosphorus oxychloride for about 5 h. After monitoring by TLC, the reaction mixture was cooled to room temperature and poured into crushed ice. The separated solid was filtered, dried and recrystallized from methanol.

In the second step the intermediate 6-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-3-thiol (1 eq.) was treated with benzyl bromide (1.1 eq.) in ethanol. The reaction mixture was refluxed for 5 h. After completion of the reaction, the reaction mixture was cooled to room temperature. The isolated solid product was filtered and washed with ethanol. Recrystallization was from ethanol.

Structure description top

For the pharmocological properties of isoxazole, see: Kuz'min et al. (2007); Yermolina et al. (2011); Lilienkampf et al. (2010); Kamal et al. (2011). For the bioactivity of 1,2,4-triazoles coupled with the thiadiazole heterocylic ring system, see: Singh & Singh (2009). For biological applications, such as antimicrobial, anticancer, antiviral and antihelmentic properties, see: Habib et al. (1997); Bhat et al. (2004); Farghaly et al. (2006); Khalil et al. (1999). For the synthesis, see: Vaarla & Rao (2014). For a similar structure, see: Dinçer et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. View of the molecular packing of the title compound down the b axis. All H atoms have been omitted for clarity.

3-Benzylsulfanyl-6-(5-methyl-1,2-oxazol-3-yl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole top

Crystal data top

C₁₄H₁₁N₅OS₂	F(000) = 680
M_r = 329.40	D_x = 1.497 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 5610 reflections
a = 16.271 (5) Å	θ = 5.0–55.6°
b = 5.3804 (13) Å	µ = 0.37 mm⁻¹
c = 16.700 (4) Å	T = 296 K
V = 1462.0 (7) Å³	Block, colourless
Z = 4	0.50 × 0.45 × 0.30 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3117 independent reflections
Radiation source: fine-focus sealed tube	2905 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and φ scan	θ_max = 28.4°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −20→21
T_min = 0.836, T_max = 0.896	k = −6→7
10433 measured reflections	l = −16→21

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.031	w = 1/[σ²(F_o²) + (0.0411P)² + 0.1925P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.077	(Δ/σ)_max = 0.001
S = 1.08	Δρ_max = 0.18 e Å⁻³
3117 reflections	Δρ_min = −0.20 e Å⁻³
200 parameters	Absolute structure: Flack (1983)
1 restraint	Absolute structure parameter: 0.02 (2)

Crystal data top

C₁₄H₁₁N₅OS₂	V = 1462.0 (7) Å³
M_r = 329.40	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 16.271 (5) Å	µ = 0.37 mm⁻¹
b = 5.3804 (13) Å	T = 296 K
c = 16.700 (4) Å	0.50 × 0.45 × 0.30 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3117 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2905 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.896	R_int = 0.027
10433 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.077	Δρ_max = 0.18 e Å⁻³
S = 1.08	Δρ_min = −0.20 e Å⁻³
3117 reflections	Absolute structure: Flack (1983)
200 parameters	Absolute structure parameter: 0.02 (2)
1 restraint

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
S1	0.58876 (4)	0.55792 (12)	0.27749 (5)	0.0430 (2)
S2	0.56435 (4)	0.13539 (13)	0.56223 (5)	0.0480 (2)
O1	0.41434 (13)	1.1668 (4)	0.26095 (13)	0.0513 (7)
N1	0.47539 (15)	0.9833 (5)	0.26294 (16)	0.0500 (9)
N2	0.51832 (12)	0.5539 (4)	0.41898 (14)	0.0359 (6)
N3	0.57592 (12)	0.3670 (4)	0.41555 (14)	0.0348 (6)
N4	0.66919 (15)	0.1462 (4)	0.35159 (18)	0.0478 (8)
N5	0.65754 (15)	0.0517 (4)	0.42870 (17)	0.0464 (8)
C1	0.30250 (19)	1.3389 (5)	0.3361 (2)	0.0539 (10)
C2	0.37083 (16)	1.1579 (4)	0.32957 (17)	0.0396 (8)
C3	0.40056 (18)	0.9771 (5)	0.37679 (18)	0.0415 (8)
C4	0.46538 (15)	0.8755 (4)	0.33223 (17)	0.0350 (7)
C5	0.52042 (14)	0.6671 (4)	0.35064 (17)	0.0342 (7)
C6	0.61891 (16)	0.3354 (4)	0.34707 (18)	0.0381 (7)
C7	0.60185 (15)	0.1833 (5)	0.46600 (18)	0.0388 (8)
C8	0.61793 (19)	0.3882 (5)	0.6143 (2)	0.0488 (9)
C9	0.70934 (17)	0.3711 (4)	0.60716 (16)	0.0391 (8)
C10	0.7528 (2)	0.5388 (5)	0.5610 (2)	0.0523 (9)
C11	0.8368 (2)	0.5174 (7)	0.5528 (3)	0.0639 (11)
C12	0.8789 (2)	0.3276 (7)	0.5891 (2)	0.0603 (11)
C13	0.8372 (2)	0.1623 (6)	0.6353 (3)	0.0628 (11)
C14	0.7532 (2)	0.1828 (6)	0.6448 (2)	0.0556 (11)
H1A	0.32400	1.49870	0.35070	0.0810*
H1B	0.26440	1.28400	0.37630	0.0810*
H1C	0.27480	1.35110	0.28550	0.0810*
H3	0.38240	0.93020	0.42740	0.0500*
H8A	0.59980	0.54590	0.59240	0.0590*
H8B	0.60300	0.38470	0.67050	0.0590*
H10	0.72510	0.66720	0.53530	0.0630*
H11	0.86540	0.63330	0.52220	0.0770*
H12	0.93530	0.31210	0.58220	0.0730*
H13	0.86540	0.03440	0.66070	0.0750*
H14	0.72560	0.06900	0.67690	0.0670*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0443 (3)	0.0412 (3)	0.0434 (4)	0.0021 (3)	0.0010 (3)	−0.0021 (3)
S2	0.0399 (3)	0.0460 (3)	0.0582 (4)	−0.0038 (3)	0.0005 (4)	0.0125 (3)
O1	0.0461 (11)	0.0513 (11)	0.0566 (15)	0.0077 (8)	−0.0012 (9)	0.0149 (10)
N1	0.0457 (13)	0.0496 (13)	0.0546 (18)	0.0096 (10)	0.0017 (11)	0.0107 (12)
N2	0.0286 (10)	0.0314 (10)	0.0476 (13)	0.0009 (7)	−0.0017 (9)	−0.0029 (9)
N3	0.0276 (9)	0.0299 (10)	0.0470 (13)	0.0001 (7)	−0.0024 (9)	−0.0055 (9)
N4	0.0436 (13)	0.0434 (12)	0.0564 (15)	0.0092 (10)	−0.0002 (12)	−0.0080 (11)
N5	0.0415 (12)	0.0367 (12)	0.0611 (16)	0.0062 (9)	−0.0050 (12)	−0.0029 (11)
C1	0.0434 (15)	0.0392 (14)	0.079 (2)	0.0064 (11)	−0.0022 (16)	0.0071 (15)
C2	0.0334 (12)	0.0312 (12)	0.0543 (17)	−0.0041 (9)	−0.0055 (11)	−0.0018 (12)
C3	0.0426 (14)	0.0345 (12)	0.0474 (17)	0.0023 (10)	−0.0002 (12)	0.0018 (12)
C4	0.0322 (11)	0.0280 (10)	0.0449 (15)	−0.0040 (8)	−0.0077 (10)	−0.0004 (10)
C5	0.0303 (11)	0.0272 (11)	0.0450 (15)	−0.0033 (8)	−0.0048 (11)	−0.0058 (10)
C6	0.0332 (12)	0.0334 (11)	0.0478 (15)	−0.0024 (9)	−0.0036 (12)	−0.0068 (11)
C7	0.0312 (12)	0.0342 (12)	0.0509 (16)	−0.0024 (9)	−0.0054 (11)	−0.0011 (11)
C8	0.0520 (17)	0.0423 (14)	0.0522 (18)	0.0040 (12)	0.0088 (14)	−0.0035 (13)
C9	0.0451 (14)	0.0368 (12)	0.0354 (14)	−0.0027 (10)	0.0008 (11)	−0.0051 (11)
C10	0.0605 (17)	0.0420 (14)	0.0544 (17)	−0.0026 (12)	−0.0032 (17)	0.0069 (14)
C11	0.059 (2)	0.0688 (19)	0.064 (2)	−0.0199 (16)	0.0027 (18)	0.0050 (18)
C12	0.0470 (17)	0.072 (2)	0.062 (2)	−0.0033 (15)	−0.0081 (15)	−0.0165 (18)
C13	0.057 (2)	0.0575 (19)	0.074 (2)	0.0046 (15)	−0.0232 (18)	0.0005 (17)
C14	0.0602 (19)	0.0467 (16)	0.060 (2)	−0.0040 (13)	−0.0082 (15)	0.0126 (15)

Geometric parameters (Å, º) top

S1—C5	1.753 (3)	C8—C9	1.495 (4)
S1—C6	1.739 (3)	C9—C10	1.382 (4)
S2—C7	1.738 (3)	C9—C14	1.390 (4)
S2—C8	1.835 (3)	C10—C11	1.378 (5)
O1—N1	1.401 (3)	C11—C12	1.371 (5)
O1—C2	1.348 (4)	C12—C13	1.359 (5)
N1—C4	1.305 (4)	C13—C14	1.380 (5)
N2—N3	1.376 (3)	C1—H1A	0.9600
N2—C5	1.294 (4)	C1—H1B	0.9600
N3—C6	1.351 (4)	C1—H1C	0.9600
N3—C7	1.366 (4)	C3—H3	0.9300
N4—N5	1.397 (4)	C8—H8A	0.9700
N4—C6	1.308 (3)	C8—H8B	0.9700
N5—C7	1.308 (4)	C10—H10	0.9300
C1—C2	1.482 (4)	C11—H11	0.9300
C2—C3	1.342 (4)	C12—H12	0.9300
C3—C4	1.402 (4)	C13—H13	0.9300
C4—C5	1.468 (3)	C14—H14	0.9300

C5—S1—C6	86.79 (13)	C10—C9—C14	117.8 (3)
C7—S2—C8	99.29 (14)	C9—C10—C11	120.6 (3)
N1—O1—C2	109.1 (2)	C10—C11—C12	120.9 (3)
O1—N1—C4	104.2 (2)	C11—C12—C13	119.3 (3)
N3—N2—C5	106.8 (2)	C12—C13—C14	120.5 (3)
N2—N3—C6	118.7 (2)	C9—C14—C13	121.0 (3)
N2—N3—C7	135.6 (2)	C2—C1—H1A	110.00
C6—N3—C7	105.7 (2)	C2—C1—H1B	109.00
N5—N4—C6	104.6 (2)	C2—C1—H1C	109.00
N4—N5—C7	109.6 (2)	H1A—C1—H1B	109.00
O1—C2—C1	115.7 (2)	H1A—C1—H1C	109.00
O1—C2—C3	109.6 (2)	H1B—C1—H1C	109.00
C1—C2—C3	134.7 (3)	C2—C3—H3	128.00
C2—C3—C4	104.0 (3)	C4—C3—H3	128.00
N1—C4—C3	113.0 (2)	S2—C8—H8A	109.00
N1—C4—C5	116.7 (2)	S2—C8—H8B	109.00
C3—C4—C5	130.2 (3)	C9—C8—H8A	109.00
S1—C5—N2	118.27 (17)	C9—C8—H8B	109.00
S1—C5—C4	119.8 (2)	H8A—C8—H8B	108.00
N2—C5—C4	121.9 (2)	C9—C10—H10	120.00
S1—C6—N3	109.44 (17)	C11—C10—H10	120.00
S1—C6—N4	138.7 (2)	C10—C11—H11	120.00
N3—C6—N4	111.9 (3)	C12—C11—H11	119.00
S2—C7—N3	124.7 (2)	C11—C12—H12	120.00
S2—C7—N5	127.1 (2)	C13—C12—H12	120.00
N3—C7—N5	108.2 (3)	C12—C13—H13	120.00
S2—C8—C9	112.91 (19)	C14—C13—H13	120.00
C8—C9—C10	120.9 (2)	C9—C14—H14	120.00
C8—C9—C14	121.3 (2)	C13—C14—H14	119.00

C5—S1—C6—N4	178.0 (3)	N5—N4—C6—N3	−0.3 (3)
C6—S1—C5—N2	−0.6 (2)	N5—N4—C6—S1	−178.5 (2)
C6—S1—C5—C4	−178.2 (2)	C6—N4—N5—C7	0.5 (3)
C5—S1—C6—N3	−0.21 (18)	N4—N5—C7—N3	−0.4 (3)
C8—S2—C7—N5	104.8 (3)	N4—N5—C7—S2	178.5 (2)
C8—S2—C7—N3	−76.5 (2)	C1—C2—C3—C4	178.8 (3)
C7—S2—C8—C9	−58.4 (2)	O1—C2—C3—C4	−0.1 (3)
N1—O1—C2—C1	−179.0 (2)	C2—C3—C4—C5	−178.1 (3)
C2—O1—N1—C4	−0.2 (3)	C2—C3—C4—N1	−0.1 (3)
N1—O1—C2—C3	0.1 (3)	C3—C4—C5—N2	−5.1 (4)
O1—N1—C4—C3	0.1 (3)	N1—C4—C5—S1	−5.5 (3)
O1—N1—C4—C5	178.5 (2)	N1—C4—C5—N2	176.9 (2)
C5—N2—N3—C6	−1.3 (3)	C3—C4—C5—S1	172.5 (2)
N3—N2—C5—C4	178.7 (2)	S2—C8—C9—C10	109.4 (3)
N3—N2—C5—S1	1.1 (3)	S2—C8—C9—C14	−68.8 (3)
C5—N2—N3—C7	−178.4 (3)	C8—C9—C10—C11	−178.1 (3)
N2—N3—C7—S2	−1.4 (4)	C14—C9—C10—C11	0.2 (5)
N2—N3—C6—N4	−177.8 (2)	C8—C9—C14—C13	177.4 (3)
C6—N3—C7—N5	0.2 (3)	C10—C9—C14—C13	−1.0 (5)
C7—N3—C6—N4	0.1 (3)	C9—C10—C11—C12	1.0 (6)
C7—N3—C6—S1	178.79 (17)	C10—C11—C12—C13	−1.6 (6)
N2—N3—C6—S1	0.9 (3)	C11—C12—C13—C14	0.9 (6)
N2—N3—C7—N5	177.6 (3)	C12—C13—C14—C9	0.4 (6)
C6—N3—C7—S2	−178.7 (2)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₅OS₂
M_r	329.40
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	16.271 (5), 5.3804 (13), 16.700 (4)
V (Å³)	1462.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.50 × 0.45 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.836, 0.896
No. of measured, independent and observed [I > 2σ(I)] reflections	10433, 3117, 2905
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.077, 1.08
No. of reflections	3117
No. of parameters	200
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20
Absolute structure	Flack (1983)
Absolute structure parameter	0.02 (2)

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Acknowledgements

We are thankful to the Director N.I.T. Warangal for providing research facilities. KV express thanks to University Grants Commission–New Delhi (UGC) for a Senior Research Fellowship. The authors are thankful to SAIF–KOCHI–Cochin University, India, for providing the single crystal X-ray data.

References

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