(E)-1-(2-Amino-phen-yl)-3-(thio-phen-2-yl)prop-2-en-1-one.

The mol-ecule of the title heteroaryl chalcone derivative, C13H11NOS, exists in a trans-configuaration and is almost planar with a dihedral angle of 3.73 (8)° between the phenyl and thio-phene rings. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, two adjacent mol-ecules are linked into a dimer in an anti-parallel face-to-face manner by a pair of C-H⋯O inter-actions. Neighboring dimers are further linked into chains along the c-axis direction by N-H⋯N hydrogen bonds.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2011 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Go et al. (2005 ▶); Liu et al. (2008 ▶); Molyneux (2004 ▶); Nerya et al. (2004 ▶); Ni et al. (2004 ▶); Shenvi et al. (2013 ▶); Suwunwong et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C13H11NOS

M = 229.30

Monoclinic,

a = 24.9335 (4) Å

b = 5.0278 (1) Å

c = 18.6813 (3) Å

β = 111.151 (1)°

V = 2184.13 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.36 × 0.12 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.908, T max = 0.984

14827 measured reflections

3942 independent reflections

2620 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.127

S = 1.04

3942 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.45 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, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014189/rz5065sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014189/rz5065Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014189/rz5065Isup3.cml

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

C13H11NOS	F(000) = 960
Mr = 229.30	Dx = 1.395 Mg m−3
Monoclinic, C2/c	Melting point = 407–408 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 24.9335 (4) Å	Cell parameters from 3942 reflections
b = 5.0278 (1) Å	θ = 1.8–32.5°
c = 18.6813 (3) Å	µ = 0.27 mm−1
β = 111.151 (1)°	T = 100 K
V = 2184.13 (7) Å3	Block, yellow
Z = 8	0.36 × 0.12 × 0.06 mm

Bruker APEXII CCD area-detector diffractometer	3942 independent reflections
Radiation source: sealed tube	2620 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 32.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −37→37
Tmin = 0.908, Tmax = 0.984	k = −7→5
14827 measured reflections	l = −28→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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0488P)2 + 2.0262P] where P = (Fo2 + 2Fc2)/3
3942 reflections	(Δ/σ)max = 0.001
153 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.45 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 e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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	0.071728 (19)	−0.24213 (9)	0.38943 (3)	0.02647 (13)
O1	0.21891 (5)	0.4157 (2)	0.59945 (7)	0.0243 (3)
N1	0.22281 (6)	0.7977 (3)	0.69701 (8)	0.0196 (3)
H1N1	0.2382 (8)	0.721 (4)	0.6700 (11)	0.021 (5)*
H2N1	0.2361 (9)	0.944 (5)	0.7198 (12)	0.037 (6)*
C1	0.13438 (6)	0.5801 (3)	0.61394 (9)	0.0157 (3)
C2	0.16405 (7)	0.7756 (3)	0.66901 (9)	0.0161 (3)
C3	0.13202 (7)	0.9494 (3)	0.69732 (9)	0.0193 (3)
H3A	0.1516	1.0791	0.7346	0.023*
C4	0.07321 (7)	0.9354 (3)	0.67233 (10)	0.0210 (3)
H4A	0.0526	1.0560	0.6919	0.025*
C5	0.04342 (7)	0.7438 (3)	0.61801 (10)	0.0214 (3)
H5A	0.0027	0.7337	0.6007	0.026*
C6	0.07387 (7)	0.5711 (3)	0.59021 (9)	0.0197 (3)
H6A	0.0535	0.4408	0.5537	0.024*
C7	0.16602 (7)	0.3989 (3)	0.58064 (9)	0.0166 (3)
C8	0.13517 (7)	0.1944 (3)	0.52357 (9)	0.0176 (3)
H8A	0.0955	0.1613	0.5126	0.021*
C9	0.16398 (7)	0.0568 (3)	0.48761 (9)	0.0181 (3)
H9A	0.2034	0.1021	0.5010	0.022*
C10	0.14298 (7)	−0.1511 (3)	0.43121 (9)	0.0186 (3)
C11	0.17609 (7)	−0.3053 (3)	0.40209 (10)	0.0210 (3)
H11A	0.2166	−0.2864	0.4176	0.025*
C12	0.14450 (8)	−0.4928 (4)	0.34746 (10)	0.0267 (4)
H12A	0.1613	−0.6149	0.3228	0.032*
C13	0.08760 (8)	−0.4801 (4)	0.33398 (10)	0.0275 (4)
H13A	0.0596	−0.5897	0.2981	0.033*

	U11	U22	U33	U12	U13	U23
S1	0.0228 (2)	0.0244 (2)	0.0278 (2)	0.00019 (17)	0.00385 (17)	−0.00763 (19)
O1	0.0191 (6)	0.0249 (6)	0.0278 (7)	−0.0020 (5)	0.0071 (5)	−0.0082 (5)
N1	0.0185 (7)	0.0191 (7)	0.0187 (7)	−0.0015 (5)	0.0035 (6)	−0.0039 (6)
C1	0.0186 (7)	0.0133 (6)	0.0144 (7)	−0.0012 (6)	0.0050 (6)	0.0004 (6)
C2	0.0203 (7)	0.0143 (6)	0.0125 (7)	−0.0003 (6)	0.0043 (6)	0.0027 (6)
C3	0.0265 (8)	0.0151 (7)	0.0144 (7)	−0.0006 (6)	0.0054 (6)	−0.0005 (6)
C4	0.0265 (8)	0.0185 (7)	0.0195 (8)	0.0037 (6)	0.0100 (7)	0.0003 (6)
C5	0.0180 (7)	0.0224 (7)	0.0241 (8)	0.0004 (7)	0.0078 (6)	−0.0015 (7)
C6	0.0218 (8)	0.0172 (7)	0.0186 (8)	−0.0024 (6)	0.0056 (6)	−0.0020 (6)
C7	0.0195 (8)	0.0144 (7)	0.0151 (7)	−0.0004 (6)	0.0055 (6)	0.0012 (6)
C8	0.0190 (7)	0.0149 (7)	0.0180 (7)	−0.0012 (6)	0.0057 (6)	0.0003 (6)
C9	0.0201 (8)	0.0163 (7)	0.0172 (7)	−0.0020 (6)	0.0060 (6)	0.0001 (6)
C10	0.0241 (8)	0.0151 (7)	0.0179 (8)	−0.0014 (6)	0.0090 (6)	0.0003 (6)
C11	0.0252 (8)	0.0202 (8)	0.0228 (8)	−0.0027 (6)	0.0148 (7)	−0.0014 (6)
C12	0.0443 (11)	0.0195 (8)	0.0221 (9)	−0.0013 (8)	0.0191 (8)	−0.0029 (7)
C13	0.0384 (10)	0.0205 (8)	0.0192 (8)	−0.0038 (7)	0.0050 (7)	−0.0055 (7)

S1—C13	1.7195 (19)	C5—C6	1.373 (2)
S1—C10	1.7245 (17)	C5—H5A	0.9500
O1—C7	1.2392 (19)	C6—H6A	0.9500
N1—C2	1.371 (2)	C7—C8	1.481 (2)
N1—H1N1	0.83 (2)	C8—C9	1.340 (2)
N1—H2N1	0.86 (2)	C8—H8A	0.9500
C1—C6	1.412 (2)	C9—C10	1.442 (2)
C1—C2	1.422 (2)	C9—H9A	0.9500
C1—C7	1.481 (2)	C10—C11	1.380 (2)
C2—C3	1.409 (2)	C11—C12	1.404 (2)
C3—C4	1.371 (2)	C11—H11A	0.9500
C3—H3A	0.9500	C12—C13	1.350 (3)
C4—C5	1.402 (2)	C12—H12A	0.9500
C4—H4A	0.9500	C13—H13A	0.9500
C13—S1—C10	91.94 (9)	O1—C7—C1	120.84 (14)
C2—N1—H1N1	113.2 (13)	O1—C7—C8	118.34 (14)
C2—N1—H2N1	115.3 (14)	C1—C7—C8	120.82 (14)
H1N1—N1—H2N1	122 (2)	C9—C8—C7	119.10 (15)
C6—C1—C2	117.86 (14)	C9—C8—H8A	120.4
C6—C1—C7	121.29 (14)	C7—C8—H8A	120.4
C2—C1—C7	120.81 (14)	C8—C9—C10	128.46 (15)
N1—C2—C3	118.61 (14)	C8—C9—H9A	115.8
N1—C2—C1	122.50 (14)	C10—C9—H9A	115.8
C3—C2—C1	118.88 (14)	C11—C10—C9	125.77 (15)
C4—C3—C2	121.45 (15)	C11—C10—S1	109.74 (12)
C4—C3—H3A	119.3	C9—C10—S1	124.49 (12)
C2—C3—H3A	119.3	C10—C11—C12	113.91 (16)
C3—C4—C5	120.26 (15)	C10—C11—H11A	123.0
C3—C4—H4A	119.9	C12—C11—H11A	123.0
C5—C4—H4A	119.9	C13—C12—C11	112.33 (16)
C6—C5—C4	119.19 (15)	C13—C12—H12A	123.8
C6—C5—H5A	120.4	C11—C12—H12A	123.8
C4—C5—H5A	120.4	C12—C13—S1	112.06 (13)
C5—C6—C1	122.36 (15)	C12—C13—H13A	124.0
C5—C6—H6A	118.8	S1—C13—H13A	124.0
C1—C6—H6A	118.8
C6—C1—C2—N1	178.64 (14)	C2—C1—C7—C8	179.69 (14)
C7—C1—C2—N1	−3.6 (2)	O1—C7—C8—C9	−7.8 (2)
C6—C1—C2—C3	0.2 (2)	C1—C7—C8—C9	171.71 (14)
C7—C1—C2—C3	177.97 (14)	C7—C8—C9—C10	179.29 (15)
N1—C2—C3—C4	−179.23 (15)	C8—C9—C10—C11	−172.66 (17)
C1—C2—C3—C4	−0.7 (2)	C8—C9—C10—S1	7.8 (3)
C2—C3—C4—C5	0.7 (2)	C13—S1—C10—C11	−0.44 (13)
C3—C4—C5—C6	−0.1 (3)	C13—S1—C10—C9	179.13 (15)
C4—C5—C6—C1	−0.5 (3)	C9—C10—C11—C12	−179.72 (16)
C2—C1—C6—C5	0.4 (2)	S1—C10—C11—C12	−0.15 (18)
C7—C1—C6—C5	−177.38 (15)	C10—C11—C12—C13	0.9 (2)
C6—C1—C7—O1	176.95 (15)	C11—C12—C13—S1	−1.2 (2)
C2—C1—C7—O1	−0.8 (2)	C10—S1—C13—C12	0.96 (15)
C6—C1—C7—C8	−2.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.83 (2)	1.97 (2)	2.6253 (18)	135.6 (19)
N1—H2N1···N1i	0.86 (2)	2.34 (2)	3.184 (2)	169 (2)
C11—H11A···O1ii	0.95	2.56	3.278 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.83 (2)	1.97 (2)	2.6253 (18)	135.6 (19)
N1—H2N1⋯N1i	0.86 (2)	2.34 (2)	3.184 (2)	169 (2)
C11—H11A⋯O1ii	0.95	2.56	3.278 (2)	133

Symmetry codes: (i) ; (ii) .