3-Methyl-sulfanyl-5-phenyl-1,2,4-triazine.

In the mol-ecule of the title compound, C10H9N3S, the dihedral angle between the triazine and phenyl rings is 11.77 (7)°. In the crystal, mol-ecules are linked by π-π stacking inter-actions [centroid-centroid distances = 3.7359 (3) and 3.7944 (4) Å], forming layers parallel to the bc plane.

Related literature

For the biological activity of sulfonamides, see: Abd el-Samii (1992 ▶); Kidwai et al. (1998 ▶); Holla et al. (2001 ▶); Abdel-Rahman et al. (1999 ▶); Hay et al. (2004 ▶); Sztanke et al. (2005 ▶). For the structure of a similar compound, see: Wen et al. (2006 ▶).

Experimental

Crystal data

C10H9N3S

M = 203.26

Monoclinic,

a = 7.7513 (3) Å

b = 12.9191 (5) Å

c = 9.8262 (3) Å

β = 94.584 (2)°

V = 980.85 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.41 × 0.35 × 0.29 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.693, T max = 0.747

15588 measured reflections

2859 independent reflections

2544 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.110

S = 1.10

2859 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814011830/rz5126sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011830/rz5126Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814011830/rz5126Isup3.cml

CCDC reference: 1004529

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H9N3S	F(000) = 424
Mr = 203.26	Dx = 1.376 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2859 reflections
a = 7.7513 (3) Å	θ = 2.6–30.0°
b = 12.9191 (5) Å	µ = 0.29 mm−1
c = 9.8262 (3) Å	T = 296 K
β = 94.584 (2)°	Block, yellow
V = 980.85 (6) Å3	0.41 × 0.35 × 0.29 mm
Z = 4

Bruker X8 APEX diffractometer	2859 independent reflections
Radiation source: fine-focus sealed tube	2544 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.693, Tmax = 0.747	k = −18→16
15588 measured reflections	l = −11→13

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) = 0.110	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.210P] where P = (Fo2 + 2Fc2)/3
2859 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.32 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
S	0.23977 (4)	0.83039 (3)	0.60310 (3)	0.04391 (12)
N1	0.55958 (14)	0.87884 (9)	0.70043 (10)	0.0411 (2)
N2	0.49883 (12)	0.86358 (7)	0.45807 (9)	0.0321 (2)
N3	0.72612 (15)	0.90131 (11)	0.68242 (11)	0.0492 (3)
C1	0.2219 (2)	0.83401 (12)	0.78375 (15)	0.0478 (3)
H1A	0.1053	0.8176	0.8025	0.072*
H1B	0.2509	0.9020	0.8177	0.072*
H1C	0.2997	0.7844	0.8278	0.072*
C2	0.45673 (14)	0.86159 (8)	0.58822 (11)	0.0315 (2)
C3	0.77637 (16)	0.90344 (12)	0.55773 (13)	0.0434 (3)
H3	0.8915	0.9188	0.5461	0.052*
C4	0.66358 (14)	0.88349 (8)	0.44103 (11)	0.0308 (2)
C5	0.72027 (15)	0.88557 (8)	0.30105 (11)	0.0324 (2)
C6	0.89529 (17)	0.88858 (11)	0.27791 (14)	0.0439 (3)
H6	0.9785	0.8887	0.3515	0.053*
C7	0.9461 (2)	0.89133 (13)	0.14577 (16)	0.0537 (4)
H7	1.0631	0.8939	0.1311	0.064*
C8	0.8234 (2)	0.89027 (12)	0.03593 (15)	0.0539 (4)
H8	0.8576	0.8917	−0.0526	0.065*
C9	0.6501 (2)	0.88713 (12)	0.05779 (13)	0.0499 (3)
H9	0.5677	0.8863	−0.0164	0.060*
C10	0.59717 (17)	0.88521 (10)	0.18942 (12)	0.0403 (3)
H10	0.4799	0.8837	0.2032	0.048*

	U11	U22	U33	U12	U13	U23
S	0.03440 (17)	0.0619 (2)	0.03562 (17)	−0.00433 (12)	0.00418 (12)	0.00196 (13)
N1	0.0413 (5)	0.0550 (6)	0.0266 (4)	−0.0031 (4)	0.0003 (4)	0.0005 (4)
N2	0.0327 (4)	0.0367 (5)	0.0264 (4)	−0.0001 (3)	0.0000 (3)	0.0010 (3)
N3	0.0410 (6)	0.0750 (8)	0.0305 (5)	−0.0083 (5)	−0.0042 (4)	−0.0019 (5)
C1	0.0498 (7)	0.0555 (8)	0.0397 (7)	−0.0018 (6)	0.0137 (5)	0.0043 (5)
C2	0.0339 (5)	0.0325 (5)	0.0280 (5)	0.0015 (4)	0.0020 (4)	0.0023 (4)
C3	0.0328 (5)	0.0640 (8)	0.0324 (6)	−0.0063 (5)	−0.0023 (4)	−0.0007 (5)
C4	0.0330 (5)	0.0318 (5)	0.0271 (5)	0.0006 (4)	−0.0003 (4)	0.0008 (4)
C5	0.0374 (5)	0.0321 (5)	0.0280 (5)	0.0004 (4)	0.0033 (4)	−0.0002 (4)
C6	0.0389 (6)	0.0537 (7)	0.0396 (6)	0.0064 (5)	0.0060 (5)	0.0013 (5)
C7	0.0509 (8)	0.0642 (9)	0.0485 (8)	0.0080 (7)	0.0197 (6)	0.0016 (7)
C8	0.0753 (10)	0.0539 (8)	0.0350 (6)	0.0041 (7)	0.0192 (6)	−0.0014 (6)
C9	0.0675 (9)	0.0546 (8)	0.0271 (5)	−0.0046 (6)	−0.0002 (5)	−0.0023 (5)
C10	0.0443 (6)	0.0467 (6)	0.0294 (5)	−0.0060 (5)	−0.0006 (4)	−0.0012 (5)

S—C2	1.7469 (11)	C4—C5	1.4773 (15)
S—C1	1.7921 (14)	C5—C6	1.3939 (17)
N1—C2	1.3268 (15)	C5—C10	1.3951 (16)
N1—N3	1.3486 (16)	C6—C7	1.3872 (18)
N2—C4	1.3263 (14)	C6—H6	0.9300
N2—C2	1.3451 (14)	C7—C8	1.381 (2)
N3—C3	1.3153 (17)	C7—H7	0.9300
C1—H1A	0.9600	C8—C9	1.378 (2)
C1—H1B	0.9600	C8—H8	0.9300
C1—H1C	0.9600	C9—C10	1.3880 (17)
C3—C4	1.4091 (15)	C9—H9	0.9300
C3—H3	0.9300	C10—H10	0.9300
C2—S—C1	103.19 (6)	C6—C5—C10	119.03 (11)
C2—N1—N3	116.42 (10)	C6—C5—C4	121.21 (10)
C4—N2—C2	115.65 (9)	C10—C5—C4	119.76 (11)
C3—N3—N1	118.99 (10)	C7—C6—C5	120.43 (13)
S—C1—H1A	109.5	C7—C6—H6	119.8
S—C1—H1B	109.5	C5—C6—H6	119.8
H1A—C1—H1B	109.5	C8—C7—C6	120.11 (14)
S—C1—H1C	109.5	C8—C7—H7	119.9
H1A—C1—H1C	109.5	C6—C7—H7	119.9
H1B—C1—H1C	109.5	C9—C8—C7	119.87 (12)
N1—C2—N2	127.71 (10)	C9—C8—H8	120.1
N1—C2—S	119.19 (9)	C7—C8—H8	120.1
N2—C2—S	113.10 (8)	C8—C9—C10	120.68 (13)
N3—C3—C4	122.93 (11)	C8—C9—H9	119.7
N3—C3—H3	118.5	C10—C9—H9	119.7
C4—C3—H3	118.5	C9—C10—C5	119.88 (13)
N2—C4—C3	118.28 (10)	C9—C10—H10	120.1
N2—C4—C5	118.82 (10)	C5—C10—H10	120.1
C3—C4—C5	122.89 (10)