N-(2,4,6-Trimethyl-phen-yl)-1,3-thia-zol-2-amine.

In the title compound, C(12)H(14)N(2)S, the dihedral angle between the 1,3,5-trimethyl-benzene and 1,3-thia-zol-2-amine groups is 73.15 (4)°. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For background to the biological activities of thia­zoles, see: Wilson et al. (2001 ▶). For a related crystal structure, see: Caranoni & Capella (1982 ▶).

Experimental

Crystal data

C12H14N2S

M = 218.31

Monoclinic,

a = 14.2766 (6) Å

b = 7.0676 (2) Å

c = 13.8598 (6) Å

β = 118.736 (2)°

V = 1226.24 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.32 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.929, T max = 0.959

10086 measured reflections

2717 independent reflections

2196 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.05

2717 reflections

140 parameters

H-atom parameters constrained

Δρmax = 0.30 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031315/hb6896sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031315/hb6896Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031315/hb6896Isup3.cml

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

C12H14N2S	F(000) = 464
Mr = 218.31	Dx = 1.183 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2196 reflections
a = 14.2766 (6) Å	θ = 1.6–27.3°
b = 7.0676 (2) Å	µ = 0.23 mm−1
c = 13.8598 (6) Å	T = 296 K
β = 118.736 (2)°	Prism, yellow
V = 1226.24 (9) Å3	0.32 × 0.22 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2717 independent reflections
Radiation source: fine-focus sealed tube	2196 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 7.80 pixels mm-1	θmax = 27.3°, θmin = 1.6°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→9
Tmin = 0.929, Tmax = 0.959	l = −17→17
10086 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.3377P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2717 reflections	Δρmax = 0.30 e Å−3
140 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (4)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.28549 (3)	0.60626 (7)	0.20694 (3)	0.0510 (2)
N1	0.37642 (11)	0.6678 (2)	0.42680 (11)	0.0489 (4)
N2	0.46689 (11)	0.4830 (2)	0.35713 (11)	0.0457 (4)
C1	0.28129 (12)	0.7598 (2)	0.41025 (12)	0.0417 (5)
C2	0.25718 (15)	0.9401 (3)	0.36248 (14)	0.0503 (5)
C3	0.16150 (17)	1.0218 (3)	0.34372 (15)	0.0619 (7)
C4	0.09327 (16)	0.9380 (3)	0.37534 (15)	0.0640 (7)
C5	0.12224 (14)	0.7638 (3)	0.42681 (14)	0.0579 (6)
C6	0.21467 (13)	0.6720 (2)	0.44421 (12)	0.0464 (5)
C7	0.24324 (19)	0.4809 (3)	0.49949 (19)	0.0689 (8)
C8	0.3330 (2)	1.0470 (3)	0.3358 (2)	0.0774 (9)
C9	−0.0095 (2)	1.0332 (5)	0.3547 (2)	0.1073 (13)
C10	0.38520 (12)	0.5850 (2)	0.34340 (12)	0.0385 (4)
C11	0.36100 (15)	0.4680 (3)	0.16835 (14)	0.0522 (6)
C12	0.45154 (15)	0.4168 (3)	0.25688 (14)	0.0499 (6)
H1	0.43021	0.66451	0.49200	0.0586*
H3	0.14255	1.13832	0.30825	0.0742*
H5	0.07821	0.70656	0.45048	0.0694*
H7A	0.18460	0.43399	0.50812	0.1034*
H7B	0.30533	0.49271	0.57044	0.1034*
H7C	0.25797	0.39442	0.45505	0.1034*
H8A	0.31727	1.17980	0.33141	0.1162*
H8B	0.32495	1.00412	0.26651	0.1162*
H8C	0.40502	1.02536	0.39246	0.1162*
H9A	−0.05817	1.03567	0.27711	0.1608*
H9B	0.00533	1.16026	0.38250	0.1608*
H9C	−0.04105	0.96399	0.39150	0.1608*
H11	0.34159	0.43378	0.09636	0.0626*
H12	0.50176	0.34047	0.25128	0.0599*

	U11	U22	U33	U12	U13	U23
S1	0.0449 (3)	0.0634 (3)	0.0357 (2)	0.0060 (2)	0.0122 (2)	0.0011 (2)
N1	0.0442 (7)	0.0644 (9)	0.0332 (6)	0.0155 (7)	0.0148 (5)	0.0007 (6)
N2	0.0449 (7)	0.0542 (8)	0.0398 (7)	0.0100 (6)	0.0217 (6)	0.0047 (6)
C1	0.0410 (8)	0.0480 (9)	0.0323 (7)	0.0071 (7)	0.0147 (6)	−0.0023 (6)
C2	0.0594 (10)	0.0491 (9)	0.0441 (9)	0.0067 (8)	0.0263 (8)	0.0009 (7)
C3	0.0747 (13)	0.0597 (11)	0.0479 (10)	0.0267 (10)	0.0268 (9)	0.0082 (8)
C4	0.0539 (10)	0.0921 (15)	0.0403 (9)	0.0287 (10)	0.0182 (8)	0.0018 (9)
C5	0.0448 (9)	0.0857 (14)	0.0432 (9)	0.0020 (9)	0.0212 (7)	−0.0026 (9)
C6	0.0481 (9)	0.0532 (9)	0.0347 (7)	0.0004 (7)	0.0174 (7)	−0.0039 (7)
C7	0.0830 (14)	0.0585 (12)	0.0719 (13)	−0.0024 (10)	0.0425 (12)	0.0080 (10)
C8	0.0980 (17)	0.0590 (12)	0.0915 (17)	−0.0005 (12)	0.0585 (15)	0.0086 (11)
C9	0.0779 (16)	0.166 (3)	0.0768 (16)	0.0672 (19)	0.0362 (13)	0.0210 (17)
C10	0.0377 (7)	0.0420 (8)	0.0340 (7)	0.0021 (6)	0.0158 (6)	0.0044 (6)
C11	0.0656 (11)	0.0535 (10)	0.0407 (8)	−0.0042 (8)	0.0282 (8)	−0.0051 (7)
C12	0.0594 (10)	0.0505 (10)	0.0500 (9)	0.0078 (8)	0.0344 (8)	0.0015 (7)

S1—C10	1.7428 (15)	C6—C7	1.509 (3)
S1—C11	1.720 (2)	C11—C12	1.335 (3)
N1—C1	1.421 (2)	C3—H3	0.9300
N1—C10	1.354 (2)	C5—H5	0.9300
N2—C10	1.305 (2)	C7—H7A	0.9600
N2—C12	1.380 (2)	C7—H7B	0.9600
N1—H1	0.8600	C7—H7C	0.9600
C1—C6	1.393 (3)	C8—H8A	0.9600
C1—C2	1.401 (2)	C8—H8B	0.9600
C2—C3	1.388 (3)	C8—H8C	0.9600
C2—C8	1.505 (4)	C9—H9A	0.9600
C3—C4	1.379 (3)	C9—H9B	0.9600
C4—C5	1.383 (3)	C9—H9C	0.9600
C4—C9	1.511 (4)	C11—H11	0.9300
C5—C6	1.384 (3)	C12—H12	0.9300
C10—S1—C11	88.94 (8)	C4—C3—H3	119.00
C1—N1—C10	122.23 (14)	C4—C5—H5	119.00
C10—N2—C12	110.02 (15)	C6—C5—H5	119.00
C1—N1—H1	119.00	C6—C7—H7A	109.00
C10—N1—H1	119.00	C6—C7—H7B	109.00
N1—C1—C2	119.41 (17)	C6—C7—H7C	109.00
N1—C1—C6	119.75 (13)	H7A—C7—H7B	109.00
C2—C1—C6	120.82 (17)	H7A—C7—H7C	109.00
C1—C2—C3	117.6 (2)	H7B—C7—H7C	109.00
C3—C2—C8	120.31 (19)	C2—C8—H8A	109.00
C1—C2—C8	122.1 (2)	C2—C8—H8B	109.00
C2—C3—C4	122.9 (2)	C2—C8—H8C	109.00
C3—C4—C9	121.2 (2)	H8A—C8—H8B	109.00
C3—C4—C5	117.7 (2)	H8A—C8—H8C	109.00
C5—C4—C9	121.1 (2)	H8B—C8—H8C	110.00
C4—C5—C6	122.1 (2)	C4—C9—H9A	110.00
C1—C6—C5	118.75 (15)	C4—C9—H9B	110.00
C5—C6—C7	120.70 (19)	C4—C9—H9C	109.00
C1—C6—C7	120.55 (18)	H9A—C9—H9B	110.00
S1—C10—N2	114.35 (12)	H9A—C9—H9C	109.00
S1—C10—N1	121.78 (13)	H9B—C9—H9C	109.00
N1—C10—N2	123.87 (14)	S1—C11—H11	125.00
S1—C11—C12	110.05 (14)	C12—C11—H11	125.00
N2—C12—C11	116.6 (2)	N2—C12—H12	122.00
C2—C3—H3	119.00	C11—C12—H12	122.00
C11—S1—C10—N1	−179.66 (15)	N1—C1—C6—C5	−179.71 (14)
C11—S1—C10—N2	−0.05 (14)	N1—C1—C6—C7	0.6 (2)
C10—S1—C11—C12	0.38 (17)	C2—C1—C6—C5	2.0 (2)
C10—N1—C1—C2	−76.7 (2)	C2—C1—C6—C7	−177.69 (16)
C10—N1—C1—C6	104.96 (18)	C1—C2—C3—C4	3.6 (3)
C1—N1—C10—S1	6.9 (2)	C8—C2—C3—C4	−174.12 (19)
C1—N1—C10—N2	−172.72 (16)	C2—C3—C4—C5	−0.8 (3)
C12—N2—C10—S1	−0.29 (19)	C2—C3—C4—C9	179.1 (2)
C12—N2—C10—N1	179.31 (17)	C3—C4—C5—C6	−1.7 (3)
C10—N2—C12—C11	0.6 (3)	C9—C4—C5—C6	178.44 (18)
N1—C1—C2—C3	177.48 (15)	C4—C5—C6—C1	1.1 (3)
N1—C1—C2—C8	−4.8 (2)	C4—C5—C6—C7	−179.29 (18)
C6—C1—C2—C3	−4.2 (2)	S1—C11—C12—N2	−0.7 (3)
C6—C1—C2—C8	173.51 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.86	2.16	2.944 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.86	2.16	2.944 (2)	151

Symmetry code: (i) .