4-Methyl-sulfanyl-6-(4-pyrid-yl)-1,3,5-triazin-2-amine.

In the title compound, C(9)H(9)N(5)S, the pyridyl and triazine rings make a dihedral angle of 4.8 (2)°. In the crystal, adjacent mol-ecules are bridged by an N-H⋯N hydrogen bond, forming a helical chain running along the b axis.

Related literature

For the use of N-heterocycles in the synthesis of solid-state architectures, see: Janczak et al. (2003 ▶). For silmilar triazine derivatives, see: Ma & Che (2003 ▶).

Experimental

Crystal data

C9H9N5S

M = 219.27

Orthorhombic,

a = 3.9002 (11) Å

b = 10.111 (3) Å

c = 25.143 (7) Å

V = 991.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 298 K

0.29 × 0.08 × 0.06 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.919, T max = 0.982

5053 measured reflections

1083 independent reflections

877 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.096

S = 1.06

1083 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536811013171/ng5131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013171/ng5131Isup2.hkl

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

C9H9N5S	F(000) = 456
Mr = 219.27	Dx = 1.469 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	θ = 1.6–25.0°
a = 3.9002 (11) Å	µ = 0.30 mm−1
b = 10.111 (3) Å	T = 298 K
c = 25.143 (7) Å	Prism, colorless
V = 991.4 (5) Å3	0.29 × 0.08 × 0.06 mm
Z = 4

Bruker SMART diffractometer	1083 independent reflections
Radiation source: fine-focus sealed tube	877 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.919, Tmax = 0.982	k = −10→12
5053 measured reflections	l = −29→29

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.2208P] where P = (Fo2 + 2Fc2)/3
1083 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.24 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
N1	1.1007 (9)	0.9098 (3)	0.16248 (11)	0.0339 (8)
N2	1.0449 (9)	1.1369 (3)	0.13727 (11)	0.0343 (9)
N3	0.8318 (10)	0.9659 (3)	0.08066 (11)	0.0351 (8)
N4	0.7949 (11)	1.1828 (3)	0.05641 (13)	0.0478 (11)
H4A	0.8298	1.2657	0.0620	0.057*
H4B	0.6971	1.1574	0.0275	0.057*
N5	0.8411 (12)	0.4703 (3)	0.07660 (13)	0.0495 (10)
S1	1.3341 (3)	1.07833 (10)	0.23066 (4)	0.0426 (3)
C1	1.1382 (10)	1.0410 (4)	0.17022 (13)	0.0329 (9)
C2	0.8925 (11)	1.0938 (4)	0.09250 (14)	0.0339 (10)
C3	0.9465 (10)	0.8803 (3)	0.11698 (14)	0.0311 (10)
C4	1.3782 (12)	1.2539 (4)	0.22817 (16)	0.0508 (12)
H4C	1.4850	1.2846	0.2603	0.076*
H4D	1.1559	1.2938	0.2247	0.076*
H4E	1.5175	1.2779	0.1982	0.076*
C5	0.9850 (14)	0.5082 (4)	0.12212 (17)	0.0489 (13)
H5	1.0671	0.4430	0.1449	0.059*
C6	1.0198 (13)	0.6385 (4)	0.13752 (15)	0.0432 (12)
H6	1.1208	0.6594	0.1699	0.052*
C7	0.9028 (10)	0.7375 (3)	0.10425 (13)	0.0309 (9)
C8	0.7467 (11)	0.6986 (4)	0.05768 (15)	0.0377 (11)
H8	0.6563	0.7616	0.0346	0.045*
C9	0.7248 (12)	0.5655 (4)	0.04524 (16)	0.0460 (12)
H9	0.6230	0.5417	0.0132	0.055*

	U11	U22	U33	U12	U13	U23
N1	0.040 (2)	0.0343 (19)	0.0279 (17)	−0.0042 (17)	−0.0046 (16)	−0.0005 (13)
N2	0.041 (2)	0.0336 (17)	0.0289 (18)	−0.0003 (17)	0.0012 (17)	−0.0010 (14)
N3	0.049 (2)	0.0304 (17)	0.0264 (17)	0.0020 (18)	−0.0011 (18)	0.0006 (13)
N4	0.076 (3)	0.0345 (17)	0.0325 (19)	−0.003 (2)	−0.011 (2)	0.0013 (15)
N5	0.066 (3)	0.0368 (18)	0.046 (2)	−0.004 (2)	−0.010 (2)	0.0011 (16)
S1	0.0492 (6)	0.0466 (6)	0.0318 (5)	−0.0024 (6)	−0.0092 (5)	−0.0037 (4)
C1	0.027 (2)	0.043 (2)	0.028 (2)	−0.002 (2)	0.001 (2)	−0.0035 (17)
C2	0.040 (3)	0.038 (2)	0.0235 (19)	−0.001 (2)	0.0020 (19)	0.0013 (18)
C3	0.035 (2)	0.034 (2)	0.025 (2)	−0.0040 (19)	0.0058 (19)	−0.0016 (16)
C4	0.056 (3)	0.053 (3)	0.044 (2)	−0.002 (3)	−0.010 (3)	−0.015 (2)
C5	0.059 (3)	0.042 (3)	0.046 (3)	0.002 (2)	−0.009 (3)	0.0127 (19)
C6	0.055 (3)	0.038 (2)	0.036 (2)	−0.005 (2)	−0.013 (2)	0.0021 (19)
C7	0.031 (2)	0.037 (2)	0.0238 (19)	−0.002 (2)	0.0028 (19)	0.0000 (17)
C8	0.044 (3)	0.037 (2)	0.032 (2)	0.000 (2)	−0.002 (2)	0.0039 (16)
C9	0.060 (3)	0.041 (2)	0.037 (2)	−0.009 (3)	−0.005 (2)	−0.0029 (19)

N1—C3	1.327 (5)	C3—C7	1.488 (5)
N1—C1	1.349 (4)	C4—H4C	0.9600
N2—C1	1.326 (4)	C4—H4D	0.9600
N2—C2	1.345 (4)	C4—H4E	0.9600
N3—C3	1.336 (5)	C5—C6	1.379 (5)
N3—C2	1.348 (4)	C5—H5	0.9300
N4—C2	1.333 (5)	C6—C7	1.383 (5)
N4—H4A	0.8600	C6—H6	0.9300
N4—H4B	0.8600	C7—C8	1.377 (5)
N5—C9	1.325 (5)	C8—C9	1.384 (5)
N5—C5	1.331 (5)	C8—H8	0.9300
S1—C1	1.742 (4)	C9—H9	0.9300
S1—C4	1.785 (4)
C3—N1—C1	113.3 (3)	H4C—C4—H4D	109.5
C1—N2—C2	114.1 (3)	S1—C4—H4E	109.5
C3—N3—C2	114.4 (3)	H4C—C4—H4E	109.5
C2—N4—H4A	120.0	H4D—C4—H4E	109.5
C2—N4—H4B	120.0	N5—C5—C6	123.9 (4)
H4A—N4—H4B	120.0	N5—C5—H5	118.0
C9—N5—C5	116.5 (3)	C6—C5—H5	118.0
C1—S1—C4	103.12 (19)	C5—C6—C7	119.3 (4)
N2—C1—N1	126.8 (3)	C5—C6—H6	120.3
N2—C1—S1	120.5 (3)	C7—C6—H6	120.3
N1—C1—S1	112.7 (3)	C8—C7—C6	117.0 (4)
N4—C2—N2	118.5 (3)	C8—C7—C3	120.7 (3)
N4—C2—N3	116.6 (3)	C6—C7—C3	122.3 (3)
N2—C2—N3	124.9 (3)	C7—C8—C9	119.8 (4)
N1—C3—N3	126.5 (3)	C7—C8—H8	120.1
N1—C3—C7	117.1 (3)	C9—C8—H8	120.1
N3—C3—C7	116.3 (3)	N5—C9—C8	123.4 (4)
S1—C4—H4C	109.5	N5—C9—H9	118.3
S1—C4—H4D	109.5	C8—C9—H9	118.3
C2—N2—C1—N1	1.3 (6)	C2—N3—C3—C7	−176.7 (4)
C2—N2—C1—S1	−179.1 (3)	C9—N5—C5—C6	−0.5 (8)
C3—N1—C1—N2	−1.5 (6)	N5—C5—C6—C7	−0.5 (8)
C3—N1—C1—S1	178.9 (3)	C5—C6—C7—C8	1.9 (7)
C4—S1—C1—N2	−3.7 (4)	C5—C6—C7—C3	−177.0 (4)
C4—S1—C1—N1	176.0 (3)	N1—C3—C7—C8	−179.7 (4)
C1—N2—C2—N4	−178.8 (4)	N3—C3—C7—C8	−1.0 (6)
C1—N2—C2—N3	0.6 (6)	N1—C3—C7—C6	−0.8 (6)
C3—N3—C2—N4	177.4 (4)	N3—C3—C7—C6	177.9 (4)
C3—N3—C2—N2	−2.0 (6)	C6—C7—C8—C9	−2.4 (6)
C1—N1—C3—N3	−0.3 (6)	C3—C7—C8—C9	176.6 (4)
C1—N1—C3—C7	178.3 (3)	C5—N5—C9—C8	0.0 (7)
C2—N3—C3—N1	1.9 (6)	C7—C8—C9—N5	1.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N5i	0.86	2.10	2.956 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N5i	0.86	2.10	2.956 (4)	172

Symmetry code: (i) .