(E)-3-Dimethyl­amino-1-(2-thien­yl)prop-2-en-1-one

Bi, J.-H.

doi:10.1107/S1600536809025331

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1847

doi:10.1107/S1600536809025331

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(E)-3-Dimethylamino-1-(2-thienyl)prop-2-en-1-one

Jian-Hong Bi ^a ^*

^aDeparment of Chemistry and Chemical Engineering, Hefei Teachers College, Hefei 230061, People's Republic of China
^*Correspondence e-mail: bi010101@126.com

(Received 24 June 2009; accepted 30 June 2009; online 11 July 2009)

The molecular skeleton of the title molecule, C₉H₁₁NOS, is essentially planar: the thiophene ring is inclined to the mean plane of the rest non-H atoms by 2.92 (3)°. The crystal packing exhibits no significantly short intermolecular contacts.

Related literature

For general backgroud, see Amari et al. (1993 ). For the crystal structures of related compounds, see: Li et al. (2005 ); Hu et al. (2007 ); Bi (2009 ).

Experimental

Crystal data

C₉H₁₁NOS
M_r = 181.26
Monoclinic, P 2₁ /n
a = 5.9618 (12) Å
b = 8.1241 (16) Å
c = 19.449 (4) Å
β = 92.910 (3)°
V = 940.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 291 K
0.45 × 0.30 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.867, T_max = 0.964
4740 measured reflections
1636 independent reflections
1137 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.124
S = 1.05
1636 reflections
111 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025331/cv2582sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025331/cv2582Isup2.hkl

checkCIF report

Comment top

Many coordinated complexes derived from 2-[3-(dimethylamino)prop-2-enoyl] pyridine or thiophene have been reported recently in chemical research (Amari et al., 1993; Bi, 2009; Hu & Tian, 2007; Li et al., 2005). In continuation of our ongoing program directed to the development of similar compounds (Bi, 2009), herein we report the molecular structure of the title compound (I) - the newly synthesized ligand derived from 2-acetylthiophene.

In (I) (Fig. 1), the dihedral angle between the thiophene ring and the mean plane of the restnon-hydrogen atoms is 2.92 (3)°. The crystal packing exhibits no significantly short intermolecular contacts.

Related literature top

For general backgroud, see Amari et al. (1993). For the crystal structures of related compounds, see: Li et al. (2005); Hu et al. (2007); Bi (2009).

Experimental top

All solvents and chemicals were of analytical grade and were used without further purification. A solution of 2-acetylthiophene (0.2 mmol) and dimethoxy-N,N-dimethylmethanamine(0.2 mmol) in 150 ml DMF was refluxed for 8 h, and then concentrated to give the title compound. Single crystals suitable for X-ray analysis were grown from the methanol solution by slow evaporation at room temperature in air. Anal. Calcd.for C₉H₁₁NOS: C, 59.64; H, 6.12; N, 7.73. Found: C, 39.65; H,6.16; N, 7.71.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of (I) showing the atomic numbering and 30% probabilty displacement ellipsoids.

(E)-3-Dimethylamino-1-(2-thienyl)prop-2-en-1-one top

Crystal data top

C₉H₁₁NOS	F(000) = 384
M_r = 181.26	D_x = 1.280 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 955 reflections
a = 5.9618 (12) Å	θ = 2.7–20.2°
b = 8.1241 (16) Å	µ = 0.30 mm⁻¹
c = 19.449 (4) Å	T = 291 K
β = 92.910 (3)°	Block, yellow
V = 940.8 (3) Å³	0.45 × 0.30 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1636 independent reflections
Radiation source: fine-focus sealed tube	1137 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→6
T_min = 0.867, T_max = 0.964	k = −9→8
4740 measured reflections	l = −23→19

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) = 0.124	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0547P)² + 0.2232P] where P = (F_o² + 2F_c²)/3
1636 reflections	(Δ/σ)_max < 0.001
111 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₉H₁₁NOS	V = 940.8 (3) Å³
M_r = 181.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.9618 (12) Å	µ = 0.30 mm⁻¹
b = 8.1241 (16) Å	T = 291 K
c = 19.449 (4) Å	0.45 × 0.30 × 0.15 mm
β = 92.910 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1636 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1137 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.964	R_int = 0.034
4740 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
1636 reflections	Δρ_min = −0.29 e Å⁻³
111 parameters

Special details top

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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.

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

	x	y	z	U_iso*/U_eq
C1	0.0234 (4)	0.4667 (3)	0.16370 (13)	0.0425 (6)
C2	0.2349 (4)	0.5260 (3)	0.18109 (14)	0.0462 (7)
H2	0.3586	0.5108	0.1545	0.055*
C3	0.2416 (5)	0.6127 (3)	0.24415 (16)	0.0581 (8)
H3	0.3707	0.6620	0.2635	0.070*
C4	0.0404 (5)	0.6165 (4)	0.27337 (15)	0.0594 (8)
H4	0.0155	0.6685	0.3149	0.071*
C5	−0.0592 (4)	0.3689 (3)	0.10366 (14)	0.0479 (7)
C6	0.0996 (4)	0.3228 (3)	0.05454 (14)	0.0481 (7)
H6	0.2501	0.3510	0.0618	0.058*
C7	0.0307 (4)	0.2381 (3)	−0.00247 (14)	0.0499 (7)
H7	−0.1220	0.2142	−0.0066	0.060*
C8	0.3912 (5)	0.2183 (5)	−0.05347 (19)	0.0906 (12)
H8A	0.4146	0.3350	−0.0566	0.136*
H8B	0.4532	0.1650	−0.0922	0.136*
H8C	0.4638	0.1775	−0.0117	0.136*
C9	0.0524 (6)	0.0980 (4)	−0.11220 (15)	0.0691 (9)
H9A	−0.1052	0.0830	−0.1064	0.104*
H9B	0.1233	−0.0074	−0.1162	0.104*
H9C	0.0732	0.1611	−0.1531	0.104*
N1	0.1517 (4)	0.1844 (3)	−0.05331 (12)	0.0566 (6)
O1	−0.2623 (3)	0.3317 (3)	0.09894 (10)	0.0688 (6)
S1	−0.15994 (12)	0.51590 (10)	0.22552 (4)	0.0598 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0437 (14)	0.0414 (15)	0.0427 (15)	0.0011 (11)	0.0066 (12)	0.0028 (12)
C2	0.0414 (14)	0.0467 (16)	0.0509 (17)	−0.0023 (11)	0.0057 (12)	−0.0032 (13)
C3	0.0515 (16)	0.0588 (19)	0.0636 (19)	−0.0033 (14)	−0.0019 (14)	−0.0104 (16)
C4	0.0681 (19)	0.0601 (19)	0.0499 (18)	0.0025 (15)	0.0019 (15)	−0.0097 (15)
C5	0.0451 (15)	0.0498 (17)	0.0489 (17)	−0.0032 (12)	0.0040 (13)	0.0067 (14)
C6	0.0435 (14)	0.0520 (17)	0.0492 (17)	−0.0036 (12)	0.0065 (13)	0.0014 (14)
C7	0.0480 (16)	0.0532 (17)	0.0492 (17)	0.0003 (12)	0.0093 (14)	0.0046 (14)
C8	0.062 (2)	0.128 (3)	0.084 (3)	−0.002 (2)	0.0275 (19)	−0.016 (2)
C9	0.091 (2)	0.064 (2)	0.0531 (19)	−0.0050 (18)	0.0129 (17)	−0.0053 (17)
N1	0.0547 (14)	0.0666 (16)	0.0494 (14)	−0.0018 (12)	0.0109 (11)	−0.0068 (13)
O1	0.0444 (11)	0.0969 (16)	0.0658 (14)	−0.0154 (10)	0.0100 (10)	−0.0200 (12)
S1	0.0495 (5)	0.0741 (6)	0.0571 (5)	−0.0014 (4)	0.0145 (4)	−0.0052 (4)

Geometric parameters (Å, º) top

C1—C2	1.376 (3)	C6—H6	0.9300
C1—C5	1.476 (4)	C7—N1	1.327 (3)
C1—S1	1.713 (2)	C7—H7	0.9300
C2—C3	1.413 (4)	C8—N1	1.455 (4)
C2—H2	0.9300	C8—H8A	0.9600
C3—C4	1.353 (4)	C8—H8B	0.9600
C3—H3	0.9300	C8—H8C	0.9600
C4—S1	1.688 (3)	C9—N1	1.444 (4)
C4—H4	0.9300	C9—H9A	0.9600
C5—O1	1.247 (3)	C9—H9B	0.9600
C5—C6	1.429 (3)	C9—H9C	0.9600
C6—C7	1.351 (4)

C2—C1—C5	130.4 (2)	N1—C7—H7	115.7
C2—C1—S1	110.8 (2)	C6—C7—H7	115.7
C5—C1—S1	118.81 (18)	N1—C8—H8A	109.5
C1—C2—C3	111.9 (2)	N1—C8—H8B	109.5
C1—C2—H2	124.0	H8A—C8—H8B	109.5
C3—C2—H2	124.0	N1—C8—H8C	109.5
C4—C3—C2	112.9 (3)	H8A—C8—H8C	109.5
C4—C3—H3	123.5	H8B—C8—H8C	109.5
C2—C3—H3	123.5	N1—C9—H9A	109.5
C3—C4—S1	112.0 (2)	N1—C9—H9B	109.5
C3—C4—H4	124.0	H9A—C9—H9B	109.5
S1—C4—H4	124.0	N1—C9—H9C	109.5
O1—C5—C6	124.1 (3)	H9A—C9—H9C	109.5
O1—C5—C1	118.2 (2)	H9B—C9—H9C	109.5
C6—C5—C1	117.7 (2)	C7—N1—C9	122.3 (2)
C7—C6—C5	119.9 (2)	C7—N1—C8	120.7 (3)
C7—C6—H6	120.1	C9—N1—C8	116.9 (2)
C5—C6—H6	120.1	C4—S1—C1	92.36 (13)
N1—C7—C6	128.7 (3)

Experimental details

Crystal data
Chemical formula	C₉H₁₁NOS
M_r	181.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	5.9618 (12), 8.1241 (16), 19.449 (4)
β (°)	92.910 (3)
V (Å³)	940.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.45 × 0.30 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.867, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	4740, 1636, 1137
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.124, 1.05
No. of reflections	1636
No. of parameters	111
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author is indebted to the National Natural Science Foundation of China for financial support (grant No. 20871039).

References

Amari, C., Ianelli, S., Pelizzi, C., Pelizzi, G. & Predieri, G. (1993). Inorg. Chim. Acta, 211, 89–94. CSD CrossRef CAS Web of Science Google Scholar
Bi, J.-H. (2009). Acta Cryst. E65, m633. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, T.-L. & Tian, J.-L. (2007). Acta Cryst. E63, m1092–m1093. Web of Science CSD CrossRef IUCr Journals Google Scholar
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