N-(1,3-Thia-zol-2-yl)-2-(2,4,6-trimethyl-phen-yl)acetamide.

In the title compound, C(14)H(16)N(2)OS, the thia-zole ring is essentially planar (r.m.s. deviation = 0.005 Å) and it forms a dihedral angle of 75.21 (8)° with the benzene ring. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯N hydrogen bonds to generate R(2) (2)(8) loops.

Related literature

For general background to and related structures of the title compound, see: Fun et al. (2011a ▶,b ▶, 2012 ▶). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H16N2OS

M = 260.35

Monoclinic,

a = 16.421 (2) Å

b = 4.6397 (7) Å

c = 20.1144 (18) Å

β = 123.150 (7)°

V = 1283.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.30 × 0.25 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.932, T max = 0.979

13735 measured reflections

3748 independent reflections

2999 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.03

3748 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031595/hb6891sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031595/hb6891Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031595/hb6891Isup3.cml

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

C14H16N2OS	F(000) = 552
Mr = 260.35	Dx = 1.348 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4087 reflections
a = 16.421 (2) Å	θ = 3.0–29.9°
b = 4.6397 (7) Å	µ = 0.24 mm−1
c = 20.1144 (18) Å	T = 100 K
β = 123.150 (7)°	Block, colourless
V = 1283.1 (3) Å3	0.30 × 0.25 × 0.09 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	3748 independent reflections
Radiation source: fine-focus sealed tube	2999 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 30.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→20
Tmin = 0.932, Tmax = 0.979	k = −6→6
13735 measured reflections	l = −26→28

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.7659P] where P = (Fo2 + 2Fc2)/3
3748 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.03056 (3)	0.78584 (8)	0.83439 (2)	0.01686 (10)
O1	0.86995 (7)	0.4661 (2)	0.75301 (6)	0.0180 (2)
N1	1.06903 (9)	0.7448 (3)	0.97704 (7)	0.0176 (2)
N2	0.93660 (8)	0.4568 (3)	0.88579 (7)	0.0151 (2)
H1	0.9347	0.3871	0.9256	0.018*
C1	1.13491 (11)	0.9354 (3)	0.97864 (9)	0.0206 (3)
H1A	1.1835	1.0281	1.0262	0.025*
C2	1.12628 (11)	0.9823 (3)	0.90878 (9)	0.0203 (3)
H2A	1.1671	1.1057	0.9017	0.024*
C3	1.01013 (10)	0.6518 (3)	0.90413 (8)	0.0145 (3)
C4	0.86909 (10)	0.3723 (3)	0.80944 (8)	0.0146 (3)
C5	0.79327 (10)	0.1587 (3)	0.79947 (8)	0.0166 (3)
H5A	0.7985	0.1370	0.8506	0.020*
H5B	0.8060	−0.0318	0.7847	0.020*
C6	0.69101 (10)	0.2559 (3)	0.73607 (8)	0.0153 (3)
C7	0.64731 (10)	0.1640 (3)	0.65713 (8)	0.0158 (3)
C8	0.55387 (10)	0.2626 (3)	0.60037 (9)	0.0184 (3)
H8A	0.5238	0.1988	0.5471	0.022*
C9	0.50331 (11)	0.4500 (3)	0.61885 (9)	0.0201 (3)
C10	0.54813 (11)	0.5407 (3)	0.69713 (9)	0.0211 (3)
H10A	0.5147	0.6698	0.7109	0.025*
C11	0.64099 (11)	0.4466 (3)	0.75590 (9)	0.0180 (3)
C12	0.69872 (11)	−0.0344 (3)	0.63240 (9)	0.0209 (3)
H12A	0.6596	−0.0557	0.5745	0.031*
H12B	0.7076	−0.2234	0.6572	0.031*
H12C	0.7623	0.0469	0.6494	0.031*
C13	0.40305 (12)	0.5556 (4)	0.55574 (10)	0.0287 (4)
H13A	0.3996	0.7646	0.5607	0.043*
H13B	0.3546	0.4608	0.5624	0.043*
H13C	0.3899	0.5098	0.5032	0.043*
C14	0.68632 (12)	0.5548 (4)	0.83981 (9)	0.0251 (3)
H14A	0.6451	0.7057	0.8406	0.038*
H14B	0.7509	0.6340	0.8592	0.038*
H14C	0.6923	0.3951	0.8741	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.01899 (17)	0.02010 (18)	0.01301 (16)	−0.00305 (13)	0.00974 (14)	0.00054 (13)
O1	0.0200 (5)	0.0210 (5)	0.0134 (5)	−0.0015 (4)	0.0094 (4)	0.0009 (4)
N1	0.0188 (6)	0.0209 (6)	0.0125 (5)	−0.0052 (5)	0.0083 (5)	−0.0013 (4)
N2	0.0174 (6)	0.0170 (6)	0.0114 (5)	−0.0037 (4)	0.0082 (5)	−0.0004 (4)
C1	0.0201 (7)	0.0230 (8)	0.0167 (7)	−0.0076 (6)	0.0087 (6)	−0.0021 (6)
C2	0.0192 (7)	0.0230 (7)	0.0183 (7)	−0.0054 (6)	0.0099 (6)	0.0001 (6)
C3	0.0164 (6)	0.0145 (6)	0.0136 (6)	0.0002 (5)	0.0089 (5)	0.0007 (5)
C4	0.0160 (6)	0.0134 (6)	0.0139 (6)	0.0019 (5)	0.0077 (5)	0.0002 (5)
C5	0.0185 (7)	0.0151 (7)	0.0144 (6)	−0.0022 (5)	0.0079 (5)	0.0004 (5)
C6	0.0169 (6)	0.0133 (6)	0.0161 (6)	−0.0020 (5)	0.0092 (5)	0.0002 (5)
C7	0.0182 (6)	0.0125 (6)	0.0168 (6)	−0.0024 (5)	0.0097 (6)	−0.0009 (5)
C8	0.0181 (7)	0.0188 (7)	0.0155 (7)	−0.0037 (5)	0.0074 (6)	−0.0013 (5)
C9	0.0176 (7)	0.0211 (7)	0.0221 (7)	0.0000 (5)	0.0111 (6)	0.0034 (6)
C10	0.0217 (7)	0.0220 (8)	0.0240 (8)	0.0012 (6)	0.0155 (6)	0.0001 (6)
C11	0.0210 (7)	0.0176 (7)	0.0186 (7)	−0.0032 (5)	0.0130 (6)	−0.0020 (5)
C12	0.0245 (7)	0.0178 (7)	0.0169 (7)	0.0015 (6)	0.0091 (6)	−0.0020 (5)
C13	0.0211 (8)	0.0375 (10)	0.0267 (8)	0.0061 (7)	0.0125 (7)	0.0083 (7)
C14	0.0294 (8)	0.0288 (9)	0.0211 (8)	−0.0019 (7)	0.0164 (7)	−0.0051 (6)

S1—C2	1.7227 (16)	C7—C12	1.506 (2)
S1—C3	1.7267 (14)	C8—C9	1.386 (2)
O1—C4	1.2230 (17)	C8—H8A	0.9500
N1—C3	1.3119 (18)	C9—C10	1.389 (2)
N1—C1	1.3840 (19)	C9—C13	1.509 (2)
N2—C4	1.3709 (18)	C10—C11	1.394 (2)
N2—C3	1.3875 (18)	C10—H10A	0.9500
N2—H1	0.8794	C11—C14	1.510 (2)
C1—C2	1.351 (2)	C12—H12A	0.9800
C1—H1A	0.9500	C12—H12B	0.9800
C2—H2A	0.9500	C12—H12C	0.9800
C4—C5	1.516 (2)	C13—H13A	0.9800
C5—C6	1.519 (2)	C13—H13B	0.9800
C5—H5A	0.9900	C13—H13C	0.9800
C5—H5B	0.9900	C14—H14A	0.9800
C6—C7	1.404 (2)	C14—H14B	0.9800
C6—C11	1.405 (2)	C14—H14C	0.9800
C7—C8	1.397 (2)
C2—S1—C3	88.58 (7)	C9—C8—H8A	118.7
C3—N1—C1	108.98 (12)	C7—C8—H8A	118.7
C4—N2—C3	122.51 (12)	C8—C9—C10	118.04 (14)
C4—N2—H1	120.3	C8—C9—C13	121.07 (14)
C3—N2—H1	117.2	C10—C9—C13	120.89 (15)
C2—C1—N1	116.28 (14)	C9—C10—C11	121.49 (14)
C2—C1—H1A	121.9	C9—C10—H10A	119.3
N1—C1—H1A	121.9	C11—C10—H10A	119.3
C1—C2—S1	110.20 (11)	C10—C11—C6	119.66 (13)
C1—C2—H2A	124.9	C10—C11—C14	119.06 (14)
S1—C2—H2A	124.9	C6—C11—C14	121.28 (14)
N1—C3—N2	120.93 (12)	C7—C12—H12A	109.5
N1—C3—S1	115.96 (11)	C7—C12—H12B	109.5
N2—C3—S1	123.11 (10)	H12A—C12—H12B	109.5
O1—C4—N2	121.68 (13)	C7—C12—H12C	109.5
O1—C4—C5	122.36 (13)	H12A—C12—H12C	109.5
N2—C4—C5	115.95 (12)	H12B—C12—H12C	109.5
C4—C5—C6	111.57 (12)	C9—C13—H13A	109.5
C4—C5—H5A	109.3	C9—C13—H13B	109.5
C6—C5—H5A	109.3	H13A—C13—H13B	109.5
C4—C5—H5B	109.3	C9—C13—H13C	109.5
C6—C5—H5B	109.3	H13A—C13—H13C	109.5
H5A—C5—H5B	108.0	H13B—C13—H13C	109.5
C7—C6—C11	119.71 (13)	C11—C14—H14A	109.5
C7—C6—C5	120.39 (13)	C11—C14—H14B	109.5
C11—C6—C5	119.87 (13)	H14A—C14—H14B	109.5
C8—C7—C6	118.59 (13)	C11—C14—H14C	109.5
C8—C7—C12	119.60 (13)	H14A—C14—H14C	109.5
C6—C7—C12	121.81 (13)	H14B—C14—H14C	109.5
C9—C8—C7	122.52 (14)
C3—N1—C1—C2	−0.6 (2)	C5—C6—C7—C8	−178.83 (13)
N1—C1—C2—S1	0.76 (19)	C11—C6—C7—C12	178.50 (13)
C3—S1—C2—C1	−0.54 (13)	C5—C6—C7—C12	0.6 (2)
C1—N1—C3—N2	179.97 (13)	C6—C7—C8—C9	0.8 (2)
C1—N1—C3—S1	0.13 (17)	C12—C7—C8—C9	−178.67 (14)
C4—N2—C3—N1	174.78 (13)	C7—C8—C9—C10	−0.2 (2)
C4—N2—C3—S1	−5.40 (19)	C7—C8—C9—C13	179.08 (15)
C2—S1—C3—N1	0.23 (13)	C8—C9—C10—C11	−0.3 (2)
C2—S1—C3—N2	−179.60 (13)	C13—C9—C10—C11	−179.52 (15)
C3—N2—C4—O1	−0.3 (2)	C9—C10—C11—C6	0.1 (2)
C3—N2—C4—C5	−179.76 (13)	C9—C10—C11—C14	179.44 (14)
O1—C4—C5—C6	−49.20 (19)	C7—C6—C11—C10	0.5 (2)
N2—C4—C5—C6	130.23 (13)	C5—C6—C11—C10	178.43 (13)
C4—C5—C6—C7	92.65 (16)	C7—C6—C11—C14	−178.81 (14)
C4—C5—C6—C11	−85.24 (16)	C5—C6—C11—C14	−0.9 (2)
C11—C6—C7—C8	−0.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1i	0.88	2.08	2.9623 (19)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N1i	0.88	2.08	2.9623 (19)	175

Symmetry code: (i) .