2-(Benzo[d]thia-zol-2-ylsulfan-yl)-N-(6-methyl-2-pyrid-yl)acetamide.

In the title compound, C(15)H(13)N(3)OS(2), the pyridine ring and the benzo[d]thia-zole unit subtend a dihedral angle of 57.7 (2)°. The length of the C(sp) (2)-S bond [1.7462 (17) Å] is significantly shorter than that of the C(sp) (3)-S bond [1.8133 (18) Å]. The crystal structure is stabilized by intra-molecular N-H⋯N and inter-molecular C-H⋯O and C-H⋯N hydrogen-bond inter-actions. Furthermore, C-H⋯π inter-actions stabilize the crystal packing.

Related literature

For biologically active compounds containing the acylamide system, see: Bennasar et al. (2006 ▶); Ladziata et al. (2006 ▶). For bond-length data, see: Gao et al. (2007 ▶).

Experimental

Crystal data

C15H13N3OS2

M = 315.40

Triclinic,

a = 8.1919 (16) Å

b = 9.0818 (18) Å

c = 11.107 (2) Å

α = 74.78 (3)°

β = 89.55 (3)°

γ = 69.34 (3)°

V = 742.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 113 K

0.16 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.945, T max = 0.965

9391 measured reflections

3526 independent reflections

2615 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.092

S = 0.99

3526 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011519/at2753sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011519/at2753Isup2.hkl

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

C15H13N3OS2	Z = 2
Mr = 315.40	F(000) = 328
Triclinic, P1	Dx = 1.410 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1919 (16) Å	Cell parameters from 2582 reflections
b = 9.0818 (18) Å	θ = 1.9–27.9°
c = 11.107 (2) Å	µ = 0.36 mm−1
α = 74.78 (3)°	T = 113 K
β = 89.55 (3)°	Prism, colourless
γ = 69.34 (3)°	0.16 × 0.14 × 0.10 mm
V = 742.8 (3) Å3

Rigaku Saturn diffractometer	3526 independent reflections
Radiation source: rotating anode	2615 reflections with I > 2σ(I)
confocal	Rint = 0.048
ω scans	θmax = 27.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.945, Tmax = 0.965	k = −11→11
9391 measured reflections	l = −14→14

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) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0398P)2] where P = (Fo2 + 2Fc2)/3
3526 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.08893 (5)	1.05001 (5)	0.25028 (4)	0.02336 (13)
S2	0.20597 (5)	1.15671 (5)	0.45732 (4)	0.02242 (13)
N1	0.74042 (17)	0.74849 (16)	0.19582 (13)	0.0200 (3)
N2	0.45173 (18)	0.88209 (17)	0.12486 (14)	0.0210 (3)
N3	0.37052 (17)	1.13818 (15)	0.25715 (13)	0.0192 (3)
O1	0.24938 (15)	0.82797 (14)	0.02096 (13)	0.0320 (3)
C1	0.6056 (2)	0.74785 (18)	0.12785 (15)	0.0189 (4)
C2	0.6186 (2)	0.62959 (19)	0.06672 (16)	0.0217 (4)
H2	0.5203	0.6332	0.0196	0.026*
C3	0.7803 (2)	0.50655 (19)	0.07723 (16)	0.0233 (4)
H3	0.7949	0.4229	0.0371	0.028*
C4	0.9210 (2)	0.50511 (19)	0.14621 (16)	0.0217 (4)
H4	1.0329	0.4214	0.1533	0.026*
C5	0.8961 (2)	0.62787 (19)	0.20491 (16)	0.0204 (4)
C6	1.0426 (2)	0.6313 (2)	0.28327 (18)	0.0300 (4)
H6A	1.0281	0.7452	0.2761	0.045*
H6B	1.1550	0.5765	0.2538	0.045*
H6C	1.0403	0.5745	0.3711	0.045*
C7	0.2879 (2)	0.9140 (2)	0.07486 (16)	0.0217 (4)
C8	0.1511 (2)	1.06990 (19)	0.09143 (16)	0.0222 (4)
H8A	0.0453	1.1009	0.0339	0.027*
H8B	0.1975	1.1594	0.0676	0.027*
C9	0.2379 (2)	1.11504 (18)	0.31235 (16)	0.0193 (4)
C10	0.4590 (2)	1.19559 (18)	0.32980 (15)	0.0184 (4)
C11	0.3900 (2)	1.21228 (18)	0.44347 (16)	0.0194 (4)
C12	0.4660 (2)	1.26537 (19)	0.52672 (16)	0.0239 (4)
H12	0.4194	1.2750	0.6041	0.029*
C13	0.6122 (2)	1.3037 (2)	0.49261 (17)	0.0257 (4)
H13	0.6667	1.3405	0.5476	0.031*
C14	0.6811 (2)	1.2894 (2)	0.37940 (17)	0.0255 (4)
H14	0.7806	1.3181	0.3583	0.031*
C15	0.6076 (2)	1.23436 (19)	0.29716 (16)	0.0225 (4)
H15	0.6563	1.2231	0.2207	0.027*
H2A	0.463 (2)	0.951 (2)	0.1624 (17)	0.027 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0181 (2)	0.0224 (2)	0.0319 (3)	−0.00785 (18)	0.00497 (18)	−0.0107 (2)
S2	0.0215 (3)	0.0227 (2)	0.0215 (2)	−0.00602 (18)	0.00643 (18)	−0.00652 (18)
N1	0.0180 (7)	0.0194 (7)	0.0224 (8)	−0.0055 (6)	0.0019 (6)	−0.0072 (6)
N2	0.0166 (8)	0.0207 (7)	0.0274 (8)	−0.0035 (6)	−0.0001 (6)	−0.0139 (7)
N3	0.0175 (8)	0.0178 (7)	0.0215 (7)	−0.0049 (6)	0.0015 (6)	−0.0062 (6)
O1	0.0229 (7)	0.0330 (7)	0.0440 (8)	−0.0057 (5)	−0.0046 (6)	−0.0229 (7)
C1	0.0186 (9)	0.0183 (8)	0.0186 (8)	−0.0054 (7)	0.0036 (7)	−0.0052 (7)
C2	0.0220 (9)	0.0220 (8)	0.0237 (9)	−0.0086 (7)	0.0046 (7)	−0.0095 (7)
C3	0.0281 (10)	0.0191 (8)	0.0246 (9)	−0.0088 (7)	0.0078 (8)	−0.0094 (7)
C4	0.0206 (9)	0.0156 (8)	0.0250 (9)	−0.0032 (7)	0.0070 (7)	−0.0042 (7)
C5	0.0187 (9)	0.0191 (8)	0.0207 (9)	−0.0056 (7)	0.0046 (7)	−0.0030 (7)
C6	0.0215 (10)	0.0271 (9)	0.0374 (11)	−0.0034 (8)	−0.0007 (8)	−0.0097 (9)
C7	0.0178 (9)	0.0236 (8)	0.0230 (9)	−0.0056 (7)	0.0016 (7)	−0.0082 (8)
C8	0.0179 (9)	0.0229 (9)	0.0252 (9)	−0.0046 (7)	−0.0016 (7)	−0.0096 (8)
C9	0.0185 (9)	0.0137 (7)	0.0211 (9)	−0.0005 (6)	0.0015 (7)	−0.0047 (7)
C10	0.0198 (9)	0.0142 (7)	0.0188 (8)	−0.0036 (6)	−0.0017 (7)	−0.0041 (7)
C11	0.0194 (9)	0.0147 (8)	0.0199 (9)	−0.0023 (6)	0.0010 (7)	−0.0033 (7)
C12	0.0284 (10)	0.0212 (8)	0.0178 (9)	−0.0029 (7)	−0.0002 (7)	−0.0068 (7)
C13	0.0289 (10)	0.0201 (8)	0.0270 (10)	−0.0068 (7)	−0.0042 (8)	−0.0076 (8)
C14	0.0255 (10)	0.0233 (9)	0.0284 (10)	−0.0115 (8)	−0.0009 (8)	−0.0046 (8)
C15	0.0216 (9)	0.0241 (9)	0.0208 (9)	−0.0081 (7)	0.0043 (7)	−0.0049 (7)

S1—C9	1.7462 (17)	C4—H4	0.9500
S1—C8	1.8133 (18)	C5—C6	1.502 (2)
S2—C11	1.7444 (17)	C6—H6A	0.9800
S2—C9	1.7459 (17)	C6—H6B	0.9800
N1—C5	1.340 (2)	C6—H6C	0.9800
N1—C1	1.345 (2)	C7—C8	1.519 (2)
N2—C7	1.359 (2)	C8—H8A	0.9900
N2—C1	1.404 (2)	C8—H8B	0.9900
N2—H2A	0.863 (17)	C10—C11	1.402 (2)
N3—C9	1.297 (2)	C10—C15	1.402 (2)
N3—C10	1.395 (2)	C11—C12	1.389 (2)
O1—C7	1.2212 (19)	C12—C13	1.385 (2)
C1—C2	1.388 (2)	C12—H12	0.9500
C2—C3	1.381 (2)	C13—C14	1.393 (3)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.383 (2)	C14—C15	1.381 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.389 (2)	C15—H15	0.9500
C9—S1—C8	100.19 (8)	O1—C7—C8	121.40 (15)
C11—S2—C9	88.51 (8)	N2—C7—C8	113.96 (14)
C5—N1—C1	117.98 (13)	C7—C8—S1	113.25 (12)
C7—N2—C1	128.33 (14)	C7—C8—H8A	108.9
C7—N2—H2A	116.3 (12)	S1—C8—H8A	108.9
C1—N2—H2A	115.3 (12)	C7—C8—H8B	108.9
C9—N3—C10	110.02 (14)	S1—C8—H8B	108.9
N1—C1—C2	123.80 (15)	H8A—C8—H8B	107.7
N1—C1—N2	111.89 (13)	N3—C9—S2	116.86 (12)
C2—C1—N2	124.31 (15)	N3—C9—S1	124.62 (13)
C3—C2—C1	117.24 (15)	S2—C9—S1	118.51 (10)
C3—C2—H2	121.4	N3—C10—C11	115.18 (15)
C1—C2—H2	121.4	N3—C10—C15	124.86 (16)
C2—C3—C4	119.97 (15)	C11—C10—C15	119.96 (15)
C2—C3—H3	120.0	C12—C11—C10	121.74 (16)
C4—C3—H3	120.0	C12—C11—S2	128.85 (14)
C3—C4—C5	119.00 (16)	C10—C11—S2	109.42 (12)
C3—C4—H4	120.5	C13—C12—C11	117.45 (17)
C5—C4—H4	120.5	C13—C12—H12	121.3
N1—C5—C4	122.01 (15)	C11—C12—H12	121.3
N1—C5—C6	116.40 (14)	C12—C13—C14	121.46 (16)
C4—C5—C6	121.59 (15)	C12—C13—H13	119.3
C5—C6—H6A	109.5	C14—C13—H13	119.3
C5—C6—H6B	109.5	C15—C14—C13	121.31 (17)
H6A—C6—H6B	109.5	C15—C14—H14	119.3
C5—C6—H6C	109.5	C13—C14—H14	119.3
H6A—C6—H6C	109.5	C14—C15—C10	118.07 (16)
H6B—C6—H6C	109.5	C14—C15—H15	121.0
O1—C7—N2	124.63 (16)	C10—C15—H15	121.0
C5—N1—C1—C2	0.0 (3)	C11—S2—C9—N3	0.20 (13)
C5—N1—C1—N2	−179.13 (14)	C11—S2—C9—S1	−178.48 (10)
C7—N2—C1—N1	−173.97 (16)	C8—S1—C9—N3	−10.77 (15)
C7—N2—C1—C2	6.9 (3)	C8—S1—C9—S2	167.80 (9)
N1—C1—C2—C3	−0.1 (3)	C9—N3—C10—C11	1.10 (19)
N2—C1—C2—C3	178.95 (16)	C9—N3—C10—C15	−179.48 (14)
C1—C2—C3—C4	−0.2 (2)	N3—C10—C11—C12	178.84 (14)
C2—C3—C4—C5	0.5 (2)	C15—C10—C11—C12	−0.6 (2)
C1—N1—C5—C4	0.3 (2)	N3—C10—C11—S2	−0.95 (17)
C1—N1—C5—C6	−179.05 (15)	C15—C10—C11—S2	179.60 (12)
C3—C4—C5—N1	−0.6 (3)	C9—S2—C11—C12	−179.36 (15)
C3—C4—C5—C6	178.74 (16)	C9—S2—C11—C10	0.42 (12)
C1—N2—C7—O1	−1.3 (3)	C10—C11—C12—C13	0.8 (2)
C1—N2—C7—C8	178.66 (15)	S2—C11—C12—C13	−179.40 (12)
O1—C7—C8—S1	105.85 (18)	C11—C12—C13—C14	−0.1 (2)
N2—C7—C8—S1	−74.11 (17)	C12—C13—C14—C15	−0.8 (3)
C9—S1—C8—C7	91.58 (12)	C13—C14—C15—C10	1.1 (2)
C10—N3—C9—S2	−0.76 (17)	N3—C10—C15—C14	−179.76 (14)
C10—N3—C9—S1	177.84 (11)	C11—C10—C15—C14	−0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3	0.867 (18)	2.142 (18)	2.949 (2)	154.6 (16)
C2—H2···O1	0.95	2.30	2.890 (2)	119
C8—H8A···O1i	0.99	2.31	3.239 (2)	156
C8—H8B···N3	0.99	2.47	2.905 (2)	106
C12—H12···N1ii	0.95	2.57	3.498 (2)	166
C8—H8B···Cg2iii	0.99	2.68	3.494 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N3	0.867 (18)	2.142 (18)	2.949 (2)	154.6 (16)
C2—H2⋯O1	0.95	2.30	2.890 (2)	119
C8—H8A⋯O1i	0.99	2.31	3.239 (2)	156
C8—H8B⋯N3	0.99	2.47	2.905 (2)	106
C12—H12⋯N1ii	0.95	2.57	3.498 (2)	166
C8—H8B⋯Cg2iii	0.99	2.68	3.494 (2)	140

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 is the centroid of the N1/C1–C5 ring.