N-(Prop-2-yn-1-yl)-1,3-benzothia-zol-2-amine.

In the title compound, C(10)H(8)N(2)S, the 2-amino-benzothia-zole and propyne groups are not coplanar [dihedral angle = 71.51 (1)°]. The crystal structure is stabilized by strong inter-molecular N-H⋯N hydrogen bonds and C-H⋯C, C-H⋯π and F-type aromatic-aromatic [centroid-centroid distance = 3.7826 (12) Å] inter-actions 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 = 188.25

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.131

S = 0.88

2454 reflections

128 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035136/zj2020sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035136/zj2020Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035136/zj2020Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H8N2S	F(000) = 392
Mr = 188.25	Dx = 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

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

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(Fo2) + (0.0804P)2] where P = (Fo2 + 2Fc2)/3
2454 reflections	(Δ/σ)max = 0.05
128 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .