N-(2,6-Dimethyl-phen-yl)-2-(2-thien-yl)acetamide.

The thienyl ring in the title compound, C(14)H(15)NOS, is disordered over two diagonally opposite positions, the major component having a site-occupancy factor of 0.569 (3). The mol-ecule is highly twisted with respect to the central amide group, which is reflected in the dihedral angle formed between the thienyl and benzene rings of 77.01 (15)° [70.34 (18)° for the minor component]. In the crystal, mol-ecules self-associate into chains along [100] via N-H⋯O hydrogen bonds. The chains are reinforced by complementary C-H⋯O contacts.

Related literature

For a general overview of 2-substituted thio­phenes, see: Campaigne (1984 ▶); Kleemann et al. (2006 ▶). For recent bio­logical studies on 2-substituted thio­phenes, see: Lourenço et al. (2007 ▶).

Experimental

Crystal data

C14H15NOS

M = 245.34

Triclinic,

a = 4.7489 (2) Å

b = 11.7309 (5) Å

c = 11.8117 (4) Å

α = 100.981 (2)°

β = 95.427 (2)°

γ = 101.104 (2)°

V = 627.96 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 120 K

0.16 × 0.06 × 0.02 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.896, T max = 1.000

11243 measured reflections

2840 independent reflections

2388 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.121

S = 1.04

2840 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049782/hg2603sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049782/hg2603Isup2.hkl

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

C14H15NOS	Z = 2
Mr = 245.34	F(000) = 260
Triclinic, P1	Dx = 1.298 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7489 (2) Å	Cell parameters from 2752 reflections
b = 11.7309 (5) Å	θ = 2.9–27.5°
c = 11.8117 (4) Å	µ = 0.24 mm−1
α = 100.981 (2)°	T = 120 K
β = 95.427 (2)°	Block, pale-brown
γ = 101.104 (2)°	0.16 × 0.06 × 0.02 mm
V = 627.96 (4) Å3

Nonius KappaCCD area-detector diffractometer	2840 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2388 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.043
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.6°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→15
Tmin = 0.896, Tmax = 1.000	l = −14→15
11243 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.4276P] where P = (Fo2 + 2Fc2)/3
2840 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
O1	0.5541 (2)	0.54877 (11)	0.35576 (11)	0.0269 (3)
N1	0.1431 (3)	0.61274 (11)	0.31337 (12)	0.0198 (3)
H1	−0.0473	0.5949	0.3056	0.024*
C1	0.0819 (3)	0.31943 (14)	0.26257 (15)	0.0227 (3)	0.569 (3)
S1	0.2856 (3)	0.21398 (11)	0.27132 (12)	0.0304 (3)	0.569 (3)
C2	0.1372 (5)	0.14166 (18)	0.13388 (18)	0.0401 (5)	0.569 (3)
H2	0.1810	0.0680	0.1000	0.048*	0.569 (3)
C3	−0.0428 (5)	0.19078 (19)	0.0743 (2)	0.0431 (5)	0.569 (3)
H3	−0.1283	0.1653	−0.0048	0.052*	0.569 (3)
C4	−0.0767 (15)	0.2938 (6)	0.1609 (6)	0.0469 (15)	0.569 (3)
H4	−0.2108	0.3405	0.1432	0.056*	0.569 (3)
C1'	0.0819 (3)	0.31943 (14)	0.26257 (15)	0.0227 (3)	0.431 (3)
S1'	−0.1147 (5)	0.32153 (18)	0.13045 (17)	0.0394 (5)	0.431 (3)
C2'	−0.0428 (5)	0.19078 (19)	0.0743 (2)	0.0431 (5)	0.431 (3)
H2'	−0.1318	0.1500	−0.0018	0.052*	0.431 (3)
C3'	0.1372 (5)	0.14166 (18)	0.13388 (18)	0.0401 (5)	0.431 (3)
H3'	0.2157	0.0741	0.1085	0.048*	0.431 (3)
C4'	0.1802 (19)	0.2208 (7)	0.2491 (7)	0.0390 (18)	0.431 (3)
H4'	0.2787	0.2009	0.3140	0.047*	0.431 (3)
C5	0.1040 (3)	0.42001 (14)	0.36525 (14)	0.0216 (3)
H5A	0.1911	0.3995	0.4362	0.026*
H5B	−0.0922	0.4326	0.3774	0.026*
C6	0.2889 (3)	0.53354 (14)	0.34521 (13)	0.0199 (3)
C7	0.2832 (3)	0.72479 (14)	0.29151 (14)	0.0203 (3)
C8	0.2477 (3)	0.82854 (14)	0.36467 (14)	0.0220 (3)
C9	0.3851 (4)	0.93774 (15)	0.34462 (16)	0.0279 (4)
H9	0.3609	1.0093	0.3922	0.033*
C10	0.5560 (4)	0.94333 (16)	0.25656 (17)	0.0313 (4)
H10	0.6530	1.0183	0.2453	0.038*
C11	0.5854 (4)	0.83976 (17)	0.18487 (16)	0.0308 (4)
H11	0.7023	0.8446	0.1243	0.037*
C12	0.4471 (4)	0.72805 (16)	0.19947 (14)	0.0254 (4)
C13	0.0684 (4)	0.82262 (15)	0.46287 (15)	0.0261 (4)
H13A	−0.1323	0.7830	0.4311	0.039*
H13B	0.0740	0.9034	0.5059	0.039*
H13C	0.1469	0.7776	0.5155	0.039*
C14	0.4706 (4)	0.61673 (17)	0.11603 (16)	0.0339 (4)
H14A	0.5533	0.6381	0.0481	0.051*
H14B	0.2776	0.5652	0.0909	0.051*
H14C	0.5962	0.5745	0.1549	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0159 (5)	0.0303 (6)	0.0356 (7)	0.0055 (5)	0.0035 (5)	0.0094 (5)
N1	0.0142 (6)	0.0179 (6)	0.0263 (7)	0.0014 (5)	0.0030 (5)	0.0043 (5)
C1	0.0207 (7)	0.0205 (8)	0.0270 (8)	0.0030 (6)	0.0047 (6)	0.0062 (6)
S1	0.0376 (7)	0.0255 (5)	0.0302 (6)	0.0155 (5)	0.0043 (5)	0.0023 (4)
C2	0.0515 (12)	0.0277 (10)	0.0373 (11)	0.0033 (9)	0.0092 (9)	0.0013 (8)
C3	0.0420 (11)	0.0397 (11)	0.0403 (11)	0.0010 (9)	0.0047 (9)	−0.0009 (9)
C4	0.056 (3)	0.041 (3)	0.044 (4)	0.019 (2)	−0.007 (2)	0.009 (2)
C1'	0.0207 (7)	0.0205 (8)	0.0270 (8)	0.0030 (6)	0.0047 (6)	0.0062 (6)
S1'	0.0444 (8)	0.0388 (10)	0.0304 (10)	0.0132 (7)	−0.0092 (7)	−0.0009 (6)
C2'	0.0420 (11)	0.0397 (11)	0.0403 (11)	0.0010 (9)	0.0047 (9)	−0.0009 (9)
C3'	0.0515 (12)	0.0277 (10)	0.0373 (11)	0.0033 (9)	0.0092 (9)	0.0013 (8)
C4'	0.040 (4)	0.044 (4)	0.036 (4)	0.011 (3)	0.002 (3)	0.014 (3)
C5	0.0204 (7)	0.0190 (7)	0.0258 (8)	0.0043 (6)	0.0043 (6)	0.0051 (6)
C6	0.0184 (7)	0.0213 (7)	0.0188 (7)	0.0042 (6)	0.0030 (6)	0.0015 (6)
C7	0.0165 (7)	0.0204 (8)	0.0229 (8)	0.0016 (6)	−0.0004 (6)	0.0059 (6)
C8	0.0182 (7)	0.0226 (8)	0.0248 (8)	0.0033 (6)	0.0017 (6)	0.0059 (6)
C9	0.0275 (8)	0.0218 (8)	0.0345 (9)	0.0047 (7)	0.0040 (7)	0.0073 (7)
C10	0.0306 (9)	0.0266 (9)	0.0372 (10)	−0.0013 (7)	0.0058 (8)	0.0146 (8)
C11	0.0309 (9)	0.0358 (10)	0.0270 (9)	0.0022 (7)	0.0095 (7)	0.0125 (8)
C12	0.0238 (8)	0.0298 (9)	0.0224 (8)	0.0053 (7)	0.0028 (6)	0.0060 (7)
C13	0.0241 (8)	0.0217 (8)	0.0321 (9)	0.0038 (6)	0.0088 (7)	0.0033 (7)
C14	0.0389 (10)	0.0379 (10)	0.0237 (9)	0.0065 (8)	0.0103 (8)	0.0024 (8)

O1—C6	1.2285 (19)	C4'—H4'	0.9500
N1—C6	1.347 (2)	C5—C6	1.520 (2)
N1—C7	1.4360 (19)	C5—H5A	0.9900
N1—H1	0.8800	C5—H5B	0.9900
C1—C4	1.305 (7)	C7—C12	1.398 (2)
C1—C5	1.502 (2)	C7—C8	1.401 (2)
C1—S1	1.723 (2)	C8—C9	1.395 (2)
S1—C2	1.697 (2)	C8—C13	1.507 (2)
C2—C3	1.337 (3)	C9—C10	1.382 (3)
C2—H2	0.9500	C9—H9	0.9500
C3—C4	1.472 (7)	C10—C11	1.382 (3)
C3—H3	0.9500	C10—H10	0.9500
C4—H4	0.9500	C11—C12	1.398 (2)
C1'—C4'	1.317 (9)	C11—H11	0.9500
C1'—C5	1.502 (2)	C12—C14	1.509 (2)
C1'—S1'	1.748 (3)	C13—H13A	0.9800
S1'—C2'	1.663 (3)	C13—H13B	0.9800
C2'—C3'	1.337 (3)	C13—H13C	0.9800
C2'—H2'	0.9500	C14—H14A	0.9800
C3'—C4'	1.466 (8)	C14—H14B	0.9800
C3'—H3'	0.9500	C14—H14C	0.9800
C6—N1—C7	123.24 (13)	C6—C5—H5B	109.6
C6—N1—H1	118.4	H5A—C5—H5B	108.1
C7—N1—H1	118.4	O1—C6—N1	123.38 (15)
C4—C1—C5	130.6 (3)	O1—C6—C5	120.78 (14)
C4—C1—S1	109.9 (3)	N1—C6—C5	115.82 (13)
C5—C1—S1	119.57 (13)	C12—C7—C8	122.10 (14)
C2—S1—C1	89.60 (12)	C12—C7—N1	120.16 (14)
C3—C2—S1	118.43 (17)	C8—C7—N1	117.74 (13)
C3—C2—H2	120.8	C9—C8—C7	118.09 (15)
S1—C2—H2	120.8	C9—C8—C13	120.84 (15)
C2—C3—C4	103.3 (3)	C7—C8—C13	121.07 (14)
C2—C3—H3	128.3	C10—C9—C8	120.92 (16)
C4—C3—H3	128.3	C10—C9—H9	119.5
C1—C4—C3	118.4 (5)	C8—C9—H9	119.5
C1—C4—H4	120.8	C11—C10—C9	119.88 (16)
C3—C4—H4	120.8	C11—C10—H10	120.1
C4'—C1'—C5	132.7 (4)	C9—C10—H10	120.1
C4'—C1'—S1'	108.1 (4)	C10—C11—C12	121.52 (16)
C5—C1'—S1'	119.22 (13)	C10—C11—H11	119.2
C2'—S1'—C1'	88.81 (14)	C12—C11—H11	119.2
C3'—C2'—S1'	121.55 (19)	C11—C12—C7	117.44 (16)
C3'—C2'—H2'	119.2	C11—C12—C14	120.33 (15)
S1'—C2'—H2'	119.2	C7—C12—C14	122.21 (15)
C2'—C3'—C4'	100.8 (4)	C8—C13—H13A	109.5
C2'—C3'—H3'	129.6	C8—C13—H13B	109.5
C4'—C3'—H3'	129.6	H13A—C13—H13B	109.5
C1'—C4'—C3'	119.9 (6)	C8—C13—H13C	109.5
C1'—C4'—H4'	120.1	H13A—C13—H13C	109.5
C3'—C4'—H4'	120.1	H13B—C13—H13C	109.5
C1'—C5—C6	110.43 (13)	C12—C14—H14A	109.5
C1—C5—C6	110.43 (13)	C12—C14—H14B	109.5
C1'—C5—H5A	109.6	H14A—C14—H14B	109.5
C1—C5—H5A	109.6	C12—C14—H14C	109.5
C6—C5—H5A	109.6	H14A—C14—H14C	109.5
C1'—C5—H5B	109.6	H14B—C14—H14C	109.5
C1—C5—H5B	109.6
C4—C1—S1—C2	−0.1 (4)	C7—N1—C6—C5	179.66 (13)
C5—C1—S1—C2	179.05 (14)	C1—C5—C6—O1	−76.75 (19)
C1—S1—C2—C3	4.17 (19)	C1—C5—C6—N1	101.88 (16)
S1—C2—C3—C4	−6.2 (4)	C6—N1—C7—C12	64.1 (2)
C5—C1—C4—C3	177.3 (3)	C6—N1—C7—C8	−116.27 (17)
S1—C1—C4—C3	−3.7 (6)	C12—C7—C8—C9	−0.9 (2)
C2—C3—C4—C1	6.3 (6)	N1—C7—C8—C9	179.47 (14)
C4'—C1'—S1'—C2'	0.3 (4)	C12—C7—C8—C13	179.62 (15)
C5—C1'—S1'—C2'	−178.34 (14)	N1—C7—C8—C13	0.0 (2)
C1'—S1'—C2'—C3'	−6.5 (2)	C7—C8—C9—C10	−1.3 (3)
S1'—C2'—C3'—C4'	9.5 (4)	C13—C8—C9—C10	178.25 (16)
C5—C1'—C4'—C3'	−176.3 (3)	C8—C9—C10—C11	1.9 (3)
S1'—C1'—C4'—C3'	5.4 (7)	C9—C10—C11—C12	−0.4 (3)
C2'—C3'—C4'—C1'	−9.1 (7)	C10—C11—C12—C7	−1.6 (3)
C4'—C1'—C5—C6	112.7 (5)	C10—C11—C12—C14	176.81 (17)
S1'—C1'—C5—C6	−69.07 (18)	C8—C7—C12—C11	2.3 (2)
C4—C1—C5—C6	−78.1 (5)	N1—C7—C12—C11	−178.09 (15)
S1—C1—C5—C6	102.98 (15)	C8—C7—C12—C14	−176.12 (16)
C7—N1—C6—O1	−1.8 (2)	N1—C7—C12—C14	3.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.04	2.8701 (18)	157
C5—H5b···O1i	0.99	2.38	3.2622 (19)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.04	2.8701 (18)	157
C5—H5b⋯O1i	0.99	2.38	3.2622 (19)	148

Symmetry code: (i) .