N-(2,6-Dimethyl­phen­yl)-2-(2-thien­yl)acetamide

Ferreira de Lima, M.; de Souza, M.V.N.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536809049782

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3203

doi:10.1107/S1600536809049782

Open

access

N-(2,6-Dimethylphenyl)-2-(2-thienyl)acetamide

Marcelle Ferreira de Lima,^a Marcus V. N. de Souza,^a Edward R. T. Tiekink,^b ^* James L. Wardell ^c ‡ and Solange M. S. V. Wardell ^d

^aFioCruz – Fundação Oswaldo Cruz, Instituto de Tecnologia em Farmacos–FarManguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^cCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, and ^dCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 19 November 2009; accepted 20 November 2009; online 25 November 2009)

The thienyl ring in the title compound, C₁₄H₁₅NOS, is disordered over two diagonally opposite positions, the major component having a site-occupancy factor of 0.569 (3). The molecule 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, molecules 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_r = 245.34
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.121
S = 1.04
2840 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) x-1, y, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

2-Substituted thiophenes have been found to have various uses, for example as dyestuffs, flavour agents, drugs, and inhibitors (Campaigne, 1984). Indeed, thiophenes are present in many natural and synthetic products with a wide range of pharmacological activities (Kleemann et al., 2006). The in vitro anti-mycobacterial activities of a series of N-(aryl)-2-thiophen-2-ylacetamide derivatives were recently investigated (Lourenço et al., 2007): encouraging activities were detected for some derivatives. The search for new drugs having anti-bacterial activity against Mycobacterium tuberculosis is a vital task due to the increase of multi-drug resistant tuberculosis (MDR-TB) and AIDS cases worldwide and the increasing resistance to the currently used main line drugs such as isoniazid and rifampin (http://www.who.int/tdr/diseases/tb/default.htm). It was in this context that the title compound, (I), was synthesized.

The central O1, N1, C5 and C6 moiety in (I), Fig. 1, is planar with the maximum deviation from the least-squares plane through these atoms being 0.0072 (13) Å for the C6 atom. Otherwise, the molecule is highly twisted as seen in the values of the S1–C1–C5–C6 and C6–N1–C7–C8 torsion angles of 102.98 (15) ° (-69.07 (18) ° for the minor component of the thienyl ring) and -116.27 (17) °, respectively. The dihedral angle between the planes through the thienyl and benzene rings are 77.01 (15) and 70.34 (18) ° for the major and minor components of the disordered thienyl ring, respectively.

In the crystal structure, molecules are connected into linear supramolecular chains via C(4), {···HNC(═O)}, synthons, Table 1 and Fig. 2. Chains, which are aligned along [1 0 0], are reinforced by complementary C5–H···O1 contacts, Table 1, so that the acceptor carbonyl-O1 atom is bifurcated.

Related literature top

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 top

A solution of 2,6-dimethylaniline (2 mmol) and 2-thienylacetyl chloride (2 mmol) in tetrahydrofuran (20 ml), was stirred for 2 h at room temperature, water (30 ml) added and the mixture was extracted with ethyl acetate (2 x 20 ml). The combined organic layers were washed with saturated aqueous NaHCO₃ and brine, dried over MgSO₄, filtered, and rotary evaporated to give the crude product, (yield 90%) which was recrystallized twice from EtOH. m. pt.: 405–406 K; CG/MS: m/z [M]+.: 245. ¹H NMR [500.00 MHz, DMSO-d₆] δ: 9.46 (s, 1H, NH), 7.38 (dd, 1H, J = 6.5, 2.0 Hz), 7.05–6.97 (m, 5H), 3.82 (s, 2H, CH₂CO), 2.09 (s, 6H, Me) p.p.m. ¹³C NMR (125.0 MHz, DMSO-d₆) δ: 167.7, 137.6, 135.1, 134.8, 127.6, 126.6, 126.4, 126.2, 124.8, 36.5, 17.9 p.p.m. IR (KBr, cm^-1): ν_max 1644 (CO).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); 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).

Figures top

	Fig. 1. Molecular structure (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only the major component of the disordered thienyl ring is shown for reasons of clarity.
	Fig. 2. Supramolecular chain in (I) mediated by N–H···O hydrogen bonds (blue dashed lines). Colour code: S, yellow; O, red; N, blue; C, grey; and H, green.

N-(2,6-Dimethylphenyl)-2-(2-thienyl)acetamide top

Crystal data top

C₁₄H₁₅NOS	Z = 2
M_r = 245.34	F(000) = 260
Triclinic, P1	D_x = 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

Data collection top

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 monochromator	R_int = 0.043
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.6°
ϕ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→15
T_min = 0.896, T_max = 1.000	l = −14→15
11243 measured reflections

Refinement top

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(F_o²) + (0.0468P)² + 0.4276P] where P = (F_o² + 2F_c²)/3
2840 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₄H₁₅NOS	γ = 101.104 (2)°
M_r = 245.34	V = 627.96 (4) Å³
Triclinic, P1	Z = 2
a = 4.7489 (2) Å	Mo Kα radiation
b = 11.7309 (5) Å	µ = 0.24 mm⁻¹
c = 11.8117 (4) Å	T = 120 K
α = 100.981 (2)°	0.16 × 0.06 × 0.02 mm
β = 95.427 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2840 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2388 reflections with I > 2σ(I)
T_min = 0.896, T_max = 1.000	R_int = 0.043
11243 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	Δρ_max = 0.27 e Å⁻³
2840 reflections	Δρ_min = −0.21 e Å⁻³
175 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NOS
M_r	245.34
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	4.7489 (2), 11.7309 (5), 11.8117 (4)
α, β, γ (°)	100.981 (2), 95.427 (2), 101.104 (2)
V (Å³)	627.96 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.16 × 0.06 × 0.02

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.896, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11243, 2840, 2388
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.121, 1.04
No. of reflections	2840
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Campaigne, E. (1984). In Comprehensive Heterocyclic Chemistry, Vol. 4, edited by A. R. Katritzky C. W. & Rees, pp. 863–934. Oxford: Pergamon. Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Kleemann, A., Engel, J. B., Kutscher, B. & Reichert, D. (2006). Pharmaceutical Substances. New York, Stuttgart: Georg Thieme Verlag. Google Scholar
Lourenço, M. C. S., Vicente, F. R., Henriques, M., das, G. M. de O., Candéa, A. L. P., Gonçalves, R. S. B., Nogueira, T. C. M., Ferreira, M. de L. & de Souza, M. V. N. (2007). Bioorg. Med. Chem. Lett. 17, 6895–6898. PubMed Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar