N-(Prop-2-yn-1-yl)-1,3-benzothia­zol-2-amine

Agarwal, A.; Singh, M.K.; Singh, S.; Bhattacharya, S.; Awasthi, S.K.

doi:10.1107/S1600536811035136

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages o2637-o2638

https://doi.org/10.1107/S1600536811035136

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N-(Prop-2-yn-1-yl)-1,3-benzothiazol-2-amine

Alka Agarwal,^a ^* Manavendra Kumar Singh,^a Suryabhan Singh,^b S. Bhattacharya ^b and Satish K. Awasthi ^c ^*

^aDepartment of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi 225 001, India, ^bDepartment of Chemistry, Banaras Hindu University, Varanasi 225 001, India, and ^cChemical Biology Laboratory, Department of Chemistry, University of Delhi 110 007, India
^*Correspondence e-mail: dralka@bhu.ac.in, awasthisatish@yahoo.com

(Received 2 August 2011; accepted 27 August 2011; online 14 September 2011)

In the title compound, C₁₀H₈N₂S, the 2-aminobenzothiazole and propyne groups are not coplanar [dihedral angle = 71.51 (1)°]. The crystal structure is stabilized by strong intermolecular N—H⋯N hydrogen bonds and C—H⋯C, C—H⋯π and F-type aromatic–aromatic [centroid–centroid distance = 3.7826 (12) Å] interactions are also observed.

Related literature

For the biological activity of heterocyclic compounds, see: Xuan et al. (2001 ) and of benzothiazole and benzimidazole compounds, see: Caroti et al. (1989 ); Paget et al. (1969 ); Da Settimo et al. (1992 ); Johnson et al. (2009 ); Kus et al. (1996 ). For N—H⋯N hydrogen bonding, see: Mingos & Braga (2004 ). For F-type aromatic–aromatic interactions, see: Zhang et al. (2010 ). For details of the synthesis, see: Lilienkampf et al. (2009 ). For recently reported small crystal structures and their antimicrobial activity, see: Singh, Agarwal & Awasthi (2011 ); Singh, Agarwal, Mahawar & Awasthi (2011 ); Awasthi et al. (2009 ).

Experimental

Crystal data

C₁₀H₈N₂S
M_r = 188.25
Monoclinic, P 2₁ /c
a = 6.8048 (4) Å
b = 8.6071 (5) Å
c = 15.8244 (8) Å
β = 99.445 (5)°
V = 914.26 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 K
0.40 × 0.39 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.771, T_max = 1.000
4188 measured reflections
2454 independent reflections
1428 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.131
S = 0.88
2454 reflections
128 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1,C1,C6,N1,C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯N1ⁱ	0.87 (3)	2.05 (3)	2.910 (2)	170 (2)
C8—H8A⋯C4ⁱⁱ	0.98	2.86	3.756 (3)	153 (1)
C10—H10⋯C1ⁱⁱⁱ	0.89	2.87	3.687 (3)	153 (1)
C10—H10⋯C6ⁱⁱⁱ	0.89	2.89	3.776 (3)	174 (1)
C10—H10⋯Cg1ⁱⁱⁱ	0.89	2.74	3.548 (3)	151
Symmetry codes: (i) -x, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811035136/zj2020sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035136/zj2020Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035136/zj2020Isup3.cml

checkCIF report

Comment top

Heterocyclic compounds containing nitrogen, sulfur, oxygen etc have immense importance especially in pharmaceutical industry. Most of the modern drugs contain one or more heteroatom in their scaffold. Further, oxidation of nitrogen in heterocycle plays key role in bioactivity of these scaffolds (Xuan, et al., 2001). It is well documented that benzothiazole and benzimidazole derivatives show wide range of biological activities including antilipidemic (Caroti, et al., 1989), antimicrobial (Kus, et al., 1996), antiviral (Paget, et al., 1969) anti-inflammatory and analgesic properties (Da Settimo, et al., 1992). Moreover, 2-aminobenzimidazole/benzothiazole derivatives are common intermediate for the synthesis of various drugs. Anticancer properties of benzothiazole derivatives in cell based assays are also well documented (Johnson, et al., 2009).Our research interest involves the antimicrobial activities of small molecule (Awasthi, et al., 2009). Recently, we have reported several small crystal structures (Singh, Agarwal & Awasthi 2011, Singh, Agarwal, Mahawar et al., 2011). We report here the crystal structure of N-(prop-2-yn-1-yl)-1,3-benzothiazol-2-amine (Figure 1).

In the title compound, the C7—N2 single bond (1.342 Å) is shorter than normal C—N bond (1.47 Å) suggesting a delocalized double bond in benzothiazole moiety. Further, N2—C8 bond (1.438 Å) is also shorter than a standard C—N bond distance due to delocalization of electrons. Again, it is evident from the crystal structure that the title compound is stabilized by strong intermolecular N—H···N hydrogen bonding as well as C—H···π interactions and aromatic π···π stacking interaction resulting in the formation of supramolecular arrangement in the cystal as seen in the crystal packing along b axis (Figure 2, Table 1). The intermolecular hydrogen bond distance between N2···N1 (2.91 Å) is shorter than N···N average bond range 3.15 Å, suggesting strong hydrogen bonding (Mingos & Braga, 2004).

In the cystal packing two benzothiazole skeletons are arranged in an antiparallel fashion by F-type aromatic–aromatic interactions and form a dimer, the ring A and C of an benzothiazole skeleton stacks with the ring C and A of another adjacent benzothiazole skeleton, respectively. The distance of CgA and CgC is 3.783 Å, where CgA and CgC are the center of ring A and C, respectively and the centroid - centroid distance between two adjacent benzothiazole ring is 3.879Å (Zhang et al., 2010). 2-Aminobenzothiazole and propyne group are not co-planar with a dihedral angle of 71.51°. The torsion angles of C7—N2—C8—C9 and C10—C9—C8—N2 are found 91.1 (3) and 44 (7)° respectively. The CCDC No. of the crystal is 806158.

Related literature top

For the biological activity of heterocyclic compounds, see: Xuan et al. (2001) and of benzothiazole and benzimidazole compounds, see: Caroti et al. (1989); Paget et al. (1969); Da Settimo et al. (1992); Johnson et al. (2009); Kus et al. (1996). For N—H···N hydrogen bonding, see: Mingos & Braga (2004). For F-type aromatic–aromatic interactions, see: Zhang et al. (2010). For details of the synthesis, see: Lilienkampf et al. (2009). For recently reported related? small crystal structures and their antimicrobial activity, see: Singh, Agarwal & Awasthi (2011); Singh, Agarwal, Mahawar & Awasthi (2011); Awasthi et al. (2009).

Experimental top

The synthesis of the title compound was carried out according to the published procedure (Lilienkampf, et al., 2009). Briefly, to a solution of 2-aminobenzothaizole (0.90 g, 6 mmol) in dry acetone was added anhydrous K₂CO₃ (4.97 g m, 32 mmol) and reaction mixture was further refluxed for 15–30 minutes. Subsequently, KI (0.50 g m, 3 mmol) and propargyl bromide (0.64 ml, 7.2 mmol) were added and further refluxed the reaction mixture for 18 hrs. The reaction mixture was cooled, filtered, and the filtrate was evaporated in vacuo to give the product which was purified by column chromatography using hexane and dichloromethane (65:35) as eluent. The product was crystallized from hexane:dichloromethane (1:1). The light pink colored crystals were obtained by slow evaporation of solvent at room temperature in several days. Yield = 20%. MS (Macromass G) m/z = 188 (M⁺), R_f = 0.59 (98:2, CH₂Cl₂: MeOH), m.p.= 215°, Elemental analysis (Perkin –Elmer 240 C elemental analyzer) Calculated for: C₁₀H₈N₂S (%) C– 63.8, H-4.2, N -14.9, S-17.1, found C-63.9, H-4.5, N -14.7, S-16.9. ¹H NMR (CDCl₃), 8.35 (s, 1H, NH), 7.71–7.68 (m, 1H), 7.44–7.42(m, 1H), 7.26–7.21 (m, 1H), 7.07–7.02(m, 1H), 4.18–4.17(m, 2H, CH₂) 3.21 (s, 1H, CH).

Structure description top

For the biological activity of heterocyclic compounds, see: Xuan et al. (2001) and of benzothiazole and benzimidazole compounds, see: Caroti et al. (1989); Paget et al. (1969); Da Settimo et al. (1992); Johnson et al. (2009); Kus et al. (1996). For N—H···N hydrogen bonding, see: Mingos & Braga (2004). For F-type aromatic–aromatic interactions, see: Zhang et al. (2010). For details of the synthesis, see: Lilienkampf et al. (2009). For recently reported related? small crystal structures and their antimicrobial activity, see: Singh, Agarwal & Awasthi (2011); Singh, Agarwal, Mahawar & Awasthi (2011); Awasthi et al. (2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP diagram of the molecule with thermal ellipsoids drawn at 50% probability level Color code: White: C; yellow: S; blue: N; white: H.
	Fig. 2. Packing diagram of molecule viewed through b plane showing supramolecular arrangement, Intermolecular N—H···N hydrogen bonding, C—H···π interactions and F-type aromatic-aromatic interaction.
	Fig. 3. The formation of the title compound.

N-(Prop-2-yn-1-yl)-1,3-benzothiazol-2-amine top

Crystal data top

C₁₀H₈N₂S	F(000) = 392
M_r = 188.25	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.8048 (4) Å	Cell parameters from 1697 reflections
b = 8.6071 (5) Å	θ = 3.5–29.1°
c = 15.8244 (8) Å	µ = 0.30 mm⁻¹
β = 99.445 (5)°	T = 293 K
V = 914.26 (9) Å³	Block, light pink
Z = 4	0.40 × 0.39 × 0.38 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2454 independent reflections
Radiation source: fine-focus sealed tube	1428 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 29.1°, θ_min = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→5
T_min = 0.771, T_max = 1.000	k = −10→9
4188 measured reflections	l = −19→19

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ²(F_o²) + (0.0804P)²] where P = (F_o² + 2F_c²)/3
2454 reflections	(Δ/σ)_max = 0.05
128 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₀H₈N₂S	V = 914.26 (9) Å³
M_r = 188.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.8048 (4) Å	µ = 0.30 mm⁻¹
b = 8.6071 (5) Å	T = 293 K
c = 15.8244 (8) Å	0.40 × 0.39 × 0.38 mm
β = 99.445 (5)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2454 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1428 reflections with I > 2σ(I)
T_min = 0.771, T_max = 1.000	R_int = 0.045
4188 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	Δρ_max = 0.17 e Å⁻³
2454 reflections	Δρ_min = −0.27 e Å⁻³
128 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
HN2	−0.004 (4)	0.093 (3)	0.0660 (17)	0.085 (8)*
S1	0.42981 (8)	0.29415 (6)	0.04155 (3)	0.0554 (2)
N1	0.2087 (2)	0.08399 (18)	−0.04719 (10)	0.0464 (4)
N2	0.0971 (3)	0.1551 (2)	0.07821 (11)	0.0548 (5)
C7	0.2251 (3)	0.1665 (2)	0.02239 (12)	0.0444 (5)
C6	0.3657 (3)	0.1159 (2)	−0.09078 (12)	0.0457 (5)
C9	−0.0017 (3)	0.3891 (3)	0.14573 (12)	0.0505 (5)
C1	0.5014 (3)	0.2280 (2)	−0.05259 (13)	0.0497 (5)
C8	0.1095 (3)	0.2429 (3)	0.15623 (14)	0.0541 (5)
H8A	0.250 (2)	0.2658 (4)	0.1781 (3)	0.065*
H8B	0.0582 (7)	0.1790 (9)	0.1993 (6)	0.065*
C2	0.6662 (4)	0.2711 (3)	−0.08909 (17)	0.0638 (7)
H2	0.750 (2)	0.3410 (19)	−0.0650 (7)	0.077*
C5	0.3948 (3)	0.0473 (3)	−0.16713 (14)	0.0577 (6)
H5	0.306 (2)	−0.0263 (18)	−0.1935 (7)	0.069*
C3	0.6923 (4)	0.2005 (3)	−0.16390 (17)	0.0705 (7)
H3	0.805 (3)	0.2274 (8)	−0.1895 (7)	0.085*
C4	0.5588 (4)	0.0906 (3)	−0.20341 (16)	0.0674 (7)
H4	0.5794 (6)	0.0458 (12)	−0.2544 (14)	0.081*
C10	−0.0941 (4)	0.5029 (3)	0.13609 (15)	0.0737 (7)
H10	−0.165 (2)	0.591 (2)	0.1287 (3)	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0584 (4)	0.0468 (4)	0.0591 (4)	−0.0137 (2)	0.0038 (3)	−0.0032 (2)
N1	0.0444 (9)	0.0428 (9)	0.0508 (9)	−0.0020 (7)	0.0046 (7)	−0.0031 (7)
N2	0.0561 (12)	0.0534 (11)	0.0553 (10)	−0.0136 (9)	0.0101 (9)	−0.0129 (9)
C7	0.0454 (11)	0.0370 (10)	0.0484 (10)	−0.0012 (9)	0.0009 (8)	0.0009 (8)
C6	0.0435 (11)	0.0409 (11)	0.0506 (11)	0.0074 (9)	0.0010 (9)	0.0062 (9)
C9	0.0494 (12)	0.0545 (13)	0.0476 (11)	−0.0088 (10)	0.0081 (9)	−0.0043 (9)
C1	0.0482 (11)	0.0429 (12)	0.0567 (12)	0.0018 (9)	0.0045 (9)	0.0114 (9)
C8	0.0607 (13)	0.0532 (13)	0.0480 (11)	−0.0043 (11)	0.0078 (10)	−0.0035 (10)
C2	0.0572 (14)	0.0577 (14)	0.0773 (17)	−0.0066 (11)	0.0130 (12)	0.0125 (12)
C5	0.0582 (13)	0.0584 (14)	0.0544 (12)	0.0092 (11)	0.0030 (10)	0.0013 (10)
C3	0.0617 (15)	0.0776 (19)	0.0761 (17)	0.0052 (13)	0.0227 (13)	0.0242 (14)
C4	0.0686 (16)	0.0786 (17)	0.0572 (13)	0.0226 (14)	0.0164 (12)	0.0117 (12)
C10	0.0827 (17)	0.0700 (17)	0.0664 (15)	0.0148 (15)	0.0062 (13)	−0.0025 (13)

Geometric parameters (Å, º) top

S1—C1	1.738 (2)	C1—C2	1.394 (3)
S1—C7	1.7612 (19)	C8—H8A	0.9843
N1—C7	1.299 (2)	C8—H8B	0.9843
N1—C6	1.391 (2)	C2—C3	1.368 (3)
N2—C7	1.342 (3)	C2—H2	0.8728
N2—C8	1.438 (3)	C5—C4	1.388 (3)
N2—HN2	0.87 (3)	C5—H5	0.9257
C6—C5	1.388 (3)	C3—C4	1.387 (3)
C6—C1	1.402 (3)	C3—H3	0.9510
C9—C10	1.160 (3)	C4—H4	0.9255
C9—C8	1.464 (3)	C10—H10	0.8942

C1—S1—C7	88.46 (10)	C9—C8—H8A	108.9
C7—N1—C6	110.27 (17)	N2—C8—H8B	108.9
C7—N2—C8	125.02 (19)	C9—C8—H8B	108.9
C7—N2—HN2	118.2 (16)	H8A—C8—H8B	107.7
C8—N2—HN2	116.7 (16)	C3—C2—C1	117.9 (2)
N1—C7—N2	122.92 (18)	C3—C2—H2	121.1
N1—C7—S1	116.23 (15)	C1—C2—H2	121.1
N2—C7—S1	120.83 (15)	C6—C5—C4	119.0 (2)
C5—C6—N1	125.34 (19)	C6—C5—H5	120.5
C5—C6—C1	119.37 (19)	C4—C5—H5	120.5
N1—C6—C1	115.29 (17)	C2—C3—C4	121.7 (2)
C10—C9—C8	178.2 (2)	C2—C3—H3	119.2
C2—C1—C6	121.5 (2)	C4—C3—H3	119.2
C2—C1—S1	128.74 (19)	C3—C4—C5	120.6 (2)
C6—C1—S1	109.74 (14)	C3—C4—H4	119.7
N2—C8—C9	113.45 (18)	C5—C4—H4	119.7
N2—C8—H8A	108.9	C9—C10—H10	180.0

C6—N1—C7—N2	−177.76 (18)	C7—S1—C1—C2	−179.2 (2)
C6—N1—C7—S1	1.1 (2)	C7—S1—C1—C6	0.15 (15)
C8—N2—C7—N1	179.58 (19)	C7—N2—C8—C9	91.1 (3)
C8—N2—C7—S1	0.7 (3)	C10—C9—C8—N2	44 (7)
C1—S1—C7—N1	−0.77 (16)	C6—C1—C2—C3	0.0 (3)
C1—S1—C7—N2	178.15 (17)	S1—C1—C2—C3	179.24 (17)
C7—N1—C6—C5	179.50 (18)	N1—C6—C5—C4	−179.97 (17)
C7—N1—C6—C1	−1.0 (2)	C1—C6—C5—C4	0.6 (3)
C5—C6—C1—C2	−0.7 (3)	C1—C2—C3—C4	0.8 (4)
N1—C6—C1—C2	179.82 (18)	C2—C3—C4—C5	−0.9 (3)
C5—C6—C1—S1	179.97 (15)	C6—C5—C4—C3	0.2 (3)
N1—C6—C1—S1	0.4 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the S1,C1,C6,N1,C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···N1ⁱ	0.87 (3)	2.05 (3)	2.910 (2)	170 (2)
C8—H8A···C4ⁱⁱ	0.98	2.86	3.756 (3)	153 (1)
C10—H10···C1ⁱⁱⁱ	0.89	2.87	3.687 (3)	153 (1)
C10—H10···C6ⁱⁱⁱ	0.89	2.89	3.776 (3)	174 (1)
C10—H10···Cg1ⁱⁱⁱ	0.89	2.74	3.548 (3)	151

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

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂S
M_r	188.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.8048 (4), 8.6071 (5), 15.8244 (8)
β (°)	99.445 (5)
V (Å³)	914.26 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.40 × 0.39 × 0.38

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.771, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4188, 2454, 1428
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.131, 0.88
No. of reflections	2454
No. of parameters	128
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.27

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the S1,C1,C6,N1,C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···N1ⁱ	0.87 (3)	2.05 (3)	2.910 (2)	170 (2)
C8—H8A···C4ⁱⁱ	0.98	2.86	3.756 (3)	152.5 (6)
C10—H10···C1ⁱⁱⁱ	0.89	2.87	3.687 (3)	153 (1)
C10—H10···C6ⁱⁱⁱ	0.89	2.89	3.776 (3)	174 (1)
C10—H10···Cg1ⁱⁱⁱ	0.89	2.74	3.548 (3)	151

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

Acknowledgements

AA and MKS are thankful to the University Grant Commission (scheme No. 34–311/2008), New Delhi, and Banaras Hindu University (BHU), Varanasi, India, respectively, for financial assistance. The authors are highly thankful to the department of Chemistry, Banaras Hindu University, for providing the single-crystal X-ray data.

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Volume 67| Part 10| October 2011| Pages o2637-o2638

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