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

The methyl-ene C atom in the title compound, C(13)H(16)N(2)S, is connected to a five-membered thia-zole ring and a mesityl substituent. The rings are aligned at 75.4 (1)°. The amino substitutent inter-acts with the ring N atom of an adjacent mol-ecule by an inter-molecular N-H⋯N hydrogen bond, generating a helical chain running along the b axis.

Related literature

For background to the synthetic procedure,: see: Yadigarov et al. (2010 ▶).

Experimental

Crystal data

C13H16N2S

M = 232.34

Monoclinic,

a = 5.5028 (5) Å

b = 30.832 (3) Å

c = 7.8355 (7) Å

β = 110.016 (1)°

V = 1249.08 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.933, T max = 0.955

7129 measured reflections

2749 independent reflections

2486 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.120

S = 1.06

2749 reflections

156 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006386/im2269sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006386/im2269Isup2.hkl

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

C13H16N2S	F(000) = 496
Mr = 232.34	Dx = 1.235 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3598 reflections
a = 5.5028 (5) Å	θ = 2.6–29.1°
b = 30.832 (3) Å	µ = 0.23 mm−1
c = 7.8355 (7) Å	T = 100 K
β = 110.016 (1)°	Prism, colorless
V = 1249.08 (19) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII diffractometer	2749 independent reflections
Radiation source: fine-focus sealed tube	2486 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.933, Tmax = 0.955	k = −40→24
7129 measured reflections	l = −9→10

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.060P)2 + 0.6878P] where P = (Fo2 + 2Fc2)/3
2749 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.38 e Å−3
2 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.65720 (8)	0.220399 (14)	0.75764 (6)	0.02680 (15)
N1	0.2450 (3)	0.26387 (5)	0.7802 (2)	0.0283 (3)
H11	0.351 (3)	0.2757 (6)	0.8795 (19)	0.030 (5)*
H12	0.080 (2)	0.2637 (8)	0.764 (3)	0.038 (6)*
N2	0.1780 (3)	0.20379 (5)	0.58369 (19)	0.0241 (3)
C1	0.3278 (3)	0.23024 (5)	0.7040 (2)	0.0215 (3)
C2	0.5821 (3)	0.17807 (6)	0.6029 (2)	0.0267 (4)
H2	0.7056	0.1604	0.5759	0.032*
C3	0.3239 (3)	0.17382 (5)	0.5263 (2)	0.0244 (3)
C4	0.1797 (4)	0.13975 (6)	0.3931 (3)	0.0338 (4)
H4A	0.0544	0.1542	0.2862	0.041*
H4B	0.0800	0.1217	0.4502	0.041*
C5	0.3520 (3)	0.11046 (6)	0.3288 (2)	0.0282 (4)
C6	0.3814 (4)	0.11748 (6)	0.1605 (2)	0.0301 (4)
C7	0.5436 (4)	0.09018 (7)	0.1069 (3)	0.0344 (4)
H7	0.5633	0.0950	−0.0075	0.041*
C8	0.6772 (4)	0.05629 (6)	0.2137 (3)	0.0344 (4)
C9	0.6454 (4)	0.04995 (6)	0.3799 (3)	0.0365 (4)
H9	0.7352	0.0269	0.4557	0.044*
C10	0.4858 (4)	0.07644 (6)	0.4388 (3)	0.0336 (4)
C11	0.2363 (5)	0.15279 (7)	0.0330 (3)	0.0473 (6)
H11A	0.2694	0.1807	0.0966	0.071*
H11B	0.0505	0.1465	−0.0085	0.071*
H11C	0.2946	0.1541	−0.0719	0.071*
C12	0.8478 (4)	0.02682 (8)	0.1499 (3)	0.0487 (6)
H12A	0.9348	0.0438	0.0820	0.073*
H12B	0.7419	0.0042	0.0711	0.073*
H12C	0.9776	0.0133	0.2552	0.073*
C13	0.4571 (7)	0.06770 (8)	0.6208 (3)	0.0609 (8)
H13A	0.5687	0.0434	0.6802	0.091*
H13B	0.2767	0.0605	0.6029	0.091*
H13C	0.5074	0.0936	0.6974	0.091*

	U11	U22	U33	U12	U13	U23
S1	0.0157 (2)	0.0299 (2)	0.0334 (3)	−0.00014 (16)	0.00646 (16)	−0.00426 (18)
N1	0.0173 (7)	0.0329 (8)	0.0320 (8)	0.0012 (6)	0.0049 (6)	−0.0077 (7)
N2	0.0193 (7)	0.0246 (7)	0.0269 (7)	−0.0006 (6)	0.0061 (5)	−0.0005 (6)
C1	0.0171 (7)	0.0248 (8)	0.0214 (7)	0.0014 (6)	0.0051 (6)	0.0038 (6)
C2	0.0229 (8)	0.0246 (8)	0.0342 (9)	0.0014 (7)	0.0118 (7)	−0.0012 (7)
C3	0.0241 (8)	0.0230 (8)	0.0267 (8)	0.0000 (7)	0.0096 (6)	0.0010 (7)
C4	0.0296 (9)	0.0303 (9)	0.0407 (10)	−0.0038 (8)	0.0110 (8)	−0.0094 (8)
C5	0.0298 (9)	0.0229 (8)	0.0295 (9)	−0.0032 (7)	0.0072 (7)	−0.0051 (7)
C6	0.0343 (9)	0.0249 (9)	0.0255 (9)	−0.0034 (7)	0.0031 (7)	−0.0002 (7)
C7	0.0414 (10)	0.0374 (11)	0.0234 (9)	−0.0047 (9)	0.0098 (8)	−0.0049 (8)
C8	0.0328 (10)	0.0319 (10)	0.0339 (10)	−0.0014 (8)	0.0055 (8)	−0.0129 (8)
C9	0.0458 (11)	0.0245 (9)	0.0292 (9)	0.0056 (8)	0.0000 (8)	−0.0014 (8)
C10	0.0489 (11)	0.0239 (9)	0.0260 (9)	−0.0024 (8)	0.0102 (8)	−0.0025 (7)
C11	0.0621 (14)	0.0328 (11)	0.0353 (11)	0.0052 (10)	0.0016 (10)	0.0071 (9)
C12	0.0402 (12)	0.0481 (13)	0.0552 (14)	0.0031 (10)	0.0127 (10)	−0.0213 (11)
C13	0.118 (2)	0.0327 (12)	0.0400 (13)	0.0024 (13)	0.0379 (15)	0.0050 (10)

S1—C2	1.7323 (18)	C7—C8	1.383 (3)
S1—C1	1.7415 (16)	C7—H7	0.9500
N1—C1	1.351 (2)	C8—C9	1.386 (3)
N1—H11	0.88 (1)	C8—C12	1.509 (3)
N1—H12	0.87 (1)	C9—C10	1.389 (3)
N2—C1	1.304 (2)	C9—H9	0.9500
N2—C3	1.396 (2)	C10—C13	1.512 (3)
C2—C3	1.346 (2)	C11—H11A	0.9800
C2—H2	0.9500	C11—H11B	0.9800
C3—C4	1.502 (2)	C11—H11C	0.9800
C4—C5	1.515 (2)	C12—H12A	0.9800
C4—H4A	0.9900	C12—H12B	0.9800
C4—H4B	0.9900	C12—H12C	0.9800
C5—C10	1.397 (3)	C13—H13A	0.9800
C5—C6	1.399 (3)	C13—H13B	0.9800
C6—C7	1.393 (3)	C13—H13C	0.9800
C6—C11	1.508 (3)
C2—S1—C1	89.03 (8)	C6—C7—H7	118.8
C1—N1—H11	119.3 (14)	C7—C8—C9	117.63 (18)
C1—N1—H12	115.1 (16)	C7—C8—C12	121.1 (2)
H11—N1—H12	118 (2)	C9—C8—C12	121.3 (2)
C1—N2—C3	110.84 (14)	C8—C9—C10	121.79 (18)
N2—C1—N1	125.03 (15)	C8—C9—H9	119.1
N2—C1—S1	114.43 (12)	C10—C9—H9	119.1
N1—C1—S1	120.50 (13)	C9—C10—C5	119.78 (17)
C3—C2—S1	110.36 (13)	C9—C10—C13	119.37 (19)
C3—C2—H2	124.8	C5—C10—C13	120.84 (19)
S1—C2—H2	124.8	C6—C11—H11A	109.5
C2—C3—N2	115.33 (15)	C6—C11—H11B	109.5
C2—C3—C4	127.16 (16)	H11A—C11—H11B	109.5
N2—C3—C4	117.47 (15)	C6—C11—H11C	109.5
C3—C4—C5	113.94 (15)	H11A—C11—H11C	109.5
C3—C4—H4A	108.8	H11B—C11—H11C	109.5
C5—C4—H4A	108.8	C8—C12—H12A	109.5
C3—C4—H4B	108.8	C8—C12—H12B	109.5
C5—C4—H4B	108.8	H12A—C12—H12B	109.5
H4A—C4—H4B	107.7	C8—C12—H12C	109.5
C10—C5—C6	119.39 (17)	H12A—C12—H12C	109.5
C10—C5—C4	120.04 (17)	H12B—C12—H12C	109.5
C6—C5—C4	120.56 (17)	C10—C13—H13A	109.5
C5—C6—C7	118.95 (17)	C10—C13—H13B	109.5
C5—C6—C11	122.00 (18)	H13A—C13—H13B	109.5
C7—C6—C11	119.01 (18)	C10—C13—H13C	109.5
C8—C7—C6	122.45 (18)	H13A—C13—H13C	109.5
C8—C7—H7	118.8	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N2i	0.88 (1)	2.06 (1)	2.907 (2)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯N2i	0.88 (1)	2.06 (1)	2.907 (2)	163 (2)

Symmetry code: (i) .