2-[2-Benzoyl-3,3-bis­(methyl­sulfan­yl)prop-2-enyl­idene]malononitrile

Joseph Nirmala; N V Unnikrishnan; E R Anabha; C Sudarsanakumar

doi:10.1107/S1600536809024635

. 2009 Jul 1;65(Pt 8):o1727. doi: 10.1107/S1600536809024635

2-[2-Benzoyl-3,3-bis(methylsulfanyl)prop-2-enylidene]malononitrile

Joseph Nirmala ^a, N V Unnikrishnan ^a, E R Anabha ^b, C Sudarsanakumar ^a,^*

PMCID: PMC2977267 PMID: 21583444

Abstract

The title compound, C₁₅H₁₂N₂OS₂, is an example of a push–pull butadiene in which the electron-releasing methylsulfanyl groups and electron-withdrawing nitrile groups on either end of the butadiene chain enhance the conjugation in the system. Short intramolecular C—H⋯S interactions are observed. In the crystal structure, an O⋯C short contact of 2.917 (3) Å is observed.

Related literature

The title compound was obtained during the synthesis of pyridene derivatives, see: Anabha & Asokan (2006 ▶). In push–pull butadienes, the C=C double bonds usually become more polarized due to π-electron delocalization (Dahne, 1978 ▶; Michalik et al., 2002 ▶). For related structures, see: Dastidar et al. (1993 ▶); Freier et al. (1999 ▶); Homrighausen & Krause Bauer (2004 ▶).

Experimental

Crystal data

C₁₅H₁₂N₂OS₂
M _r = 300.39
Monoclinic,
a = 5.6557 (2) Å
b = 8.5153 (3) Å
c = 31.4726 (11) Å
β = 90.106 (2)°
V = 1515.72 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 298 K
0.40 × 0.35 × 0.30 mm

Data collection

MacScience DIPLabo 32001 diffractometer
Absorption correction: none
9663 measured reflections
2816 independent reflections
2338 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.128
S = 1.13
2816 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024635/ci2822sup1.cif

e-65-o1727-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024635/ci2822Isup2.hkl

e-65-o1727-Isup2.hkl^{(138.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯S1	0.96	2.82	3.360 (3)	116
C12—H12⋯S1	0.93	2.66	3.040 (2)	105

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Acknowledgments

The authors are indebted to the late Dr C. V. Asokan for all the help received, especially in the synthesis of the compound. The authors acknowledge the National Single Crystal Diffractometer Facility, Department of Studies in Physics, University of Mysore, Manasagangothri, for help with the data collection. NJ is grateful to the UGC, New Delhi, Government of India, for providing a teaching fellowship.

supplementary crystallographic information

Comment

The title compound belongs to the class of push-pull butadiene as they have electron releasing methyl sulfanyl groups and electron withdrawing nitrile groups attached to the terminal carbon atoms of the butadiene moiety. The butadiene molecules are characterized by significant π-electron interactions between donor and acceptor groups and the diene double bond system. Usually C═C double bonds become more polarized due to π-electron delocalization (Dahne, 1978; Michalik et al., 2002). They are important as pivots for the synthesis of heterocycles especially pyridine derivatives. The title compound was obtained during the synthesis of pyridene derivatives (Anabha et al., 2006) and its crystal and molecular structure was determined to study the influence of aroyl group on the steriochemistry of the butadiene molecule.

A perspective view of the title molecule is shown in Fig.1. The two double bonds in the butadiene moiety are arranged in a transoid manner. The lengths of the C8—C9 [1.366 (3) Å] and C13—C12 [1.352 (3) Å] double bonds and C8—C12 [1.439 (3) Å] single bond indicate conjugation. The butadiene unit is almost planar as evidenced by the torsion angles C9—C8—C12—C13, C8—C12—C13—C14 and C12—C8—C9—S1 of -167.0 (2)°, 6.1 (4)° and 17.8 (3)°, respectively. The two methylsulfanyl groups (–SCH3) are oriented in such a way as to avoid the interaction between them as is evident from the torsion angles C10—S2—C9—C8 of -129.17 (19)° and C11—S1—C9—C8 of -148.69 (19)°. Crystal structures of other butadiene compounds reported also show similar geometric parameters (Dastidar et al.., 1993; Michalik et al., 2002; Freier et al.,1999; Homrighausen et al., 2004).

Weak intramolecular C—H···S interactions are observed (Table 1). In the crystal structure a O1···C14(1-x, y, z) short contact [2.917 (3) Å] is observed.

Experimental

2-Benzoyl-2-[3,3-bis(methylsulfanyl)-2-propylidene]malononitrile was synthesized as follows: A mixture of malononitrile (500 mg, 7.5 mmol), ammonium acetate (1.5 g, 20 mmol) and acetic acid (5 ml) was heated to 343 K and then 2-benzoyl-3,3-bis(methylsulfanyl)acrylaldehyde (5 mmol) was added. The reaction mixture was stirred for 5 minutes at the same temperature, cooled to room temperature and then poured into ice-cold water. The solid separated was filtered, dissolved in chloroform, dried over anhydrous sodium sulfate and then the solvent was evaporated. The crude product obtained was recrystallized from hexane-ethyl acetate solvent mixture.

Figures

Fig. 1. — An ORTEPII (Johnson, 1976) view of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C₁₅H₁₂N₂OS₂	F(000) = 624
M_r = 300.39	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9663 reflections
a = 5.6557 (2) Å	θ = 1.3–25.5°
b = 8.5153 (3) Å	µ = 0.35 mm⁻¹
c = 31.4726 (11) Å	T = 298 K
β = 90.106 (2)°	Block, pale yellow
V = 1515.72 (9) Å³	0.40 × 0.35 × 0.30 mm
Z = 4

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Data collection

MacScience DIPLabo 32001 diffractometer	2338 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
graphite	θ_max = 25.5°, θ_min = 1.3°
Detector resolution: 10.0 pixels mm^-1	h = −6→6
ω scans	k = −10→8
9663 measured reflections	l = −32→38
2816 independent reflections

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Refinement

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0656P)² + 0.4642P] where P = (F_o² + 2F_c²)/3
2816 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

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Special details

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.

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

	x	y	z	U_iso*/U_eq
S1	0.00111 (11)	0.11114 (7)	0.06548 (2)	0.0548 (2)
S2	−0.42287 (10)	0.19748 (8)	0.11875 (2)	0.0644 (2)
C13	0.1963 (4)	0.6023 (2)	0.06658 (7)	0.0428 (5)
C8	−0.0899 (3)	0.4037 (2)	0.09460 (6)	0.0416 (5)
O1	−0.3112 (3)	0.6304 (2)	0.11057 (6)	0.0612 (5)
C14	0.1880 (4)	0.7065 (3)	0.10221 (8)	0.0476 (5)
C7	−0.2105 (3)	0.5153 (3)	0.12490 (7)	0.0442 (5)
C4	−0.2015 (4)	0.4849 (3)	0.17132 (7)	0.0471 (5)
C9	−0.1611 (4)	0.2504 (3)	0.09308 (6)	0.0433 (5)
N1	0.1825 (4)	0.7886 (3)	0.13089 (8)	0.0688 (6)
N2	0.4570 (5)	0.6939 (3)	0.00423 (8)	0.0775 (7)
C12	0.0782 (4)	0.4644 (3)	0.06452 (7)	0.0436 (5)
H12	0.1091	0.4017	0.0410	0.052*
C15	0.3442 (4)	0.6523 (3)	0.03182 (8)	0.0531 (6)
C3	−0.0286 (5)	0.3946 (3)	0.18964 (8)	0.0632 (7)
H3	0.0884	0.3489	0.1730	0.076*
C11	−0.2165 (5)	−0.0279 (3)	0.04676 (9)	0.0673 (7)
H11A	−0.2667	−0.0931	0.0699	0.101*
H11B	−0.1483	−0.0923	0.0249	0.101*
H11C	−0.3502	0.0277	0.0354	0.101*
C10	−0.3350 (6)	0.0311 (4)	0.15069 (10)	0.0833 (9)
H10A	−0.2272	−0.0333	0.1349	0.125*
H10B	−0.4722	−0.0293	0.1581	0.125*
H10C	−0.2588	0.0675	0.1761	0.125*
C5	−0.3728 (5)	0.5550 (4)	0.19670 (8)	0.0672 (7)
H5	−0.4862	0.6200	0.1845	0.081*
C1	−0.2049 (7)	0.4371 (5)	0.25760 (9)	0.0886 (10)
H1	−0.2081	0.4190	0.2867	0.106*
C6	−0.3743 (6)	0.5282 (5)	0.23948 (10)	0.0907 (10)
H6	−0.4918	0.5726	0.2563	0.109*
C2	−0.0300 (7)	0.3719 (4)	0.23359 (10)	0.0841 (9)
H2	0.0881	0.3124	0.2465	0.101*

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0588 (4)	0.0489 (4)	0.0568 (4)	−0.0146 (3)	0.0101 (3)	−0.0086 (3)
S2	0.0452 (3)	0.0742 (5)	0.0739 (5)	−0.0231 (3)	0.0133 (3)	−0.0116 (3)
C13	0.0436 (11)	0.0424 (11)	0.0423 (11)	−0.0046 (9)	−0.0006 (8)	0.0003 (9)
C8	0.0394 (10)	0.0470 (11)	0.0384 (11)	−0.0078 (9)	−0.0043 (8)	−0.0007 (9)
O1	0.0509 (9)	0.0683 (11)	0.0644 (11)	0.0137 (8)	0.0015 (8)	0.0101 (9)
C14	0.0399 (11)	0.0470 (12)	0.0560 (14)	−0.0030 (9)	−0.0046 (9)	−0.0036 (11)
C7	0.0329 (9)	0.0503 (12)	0.0493 (12)	−0.0041 (9)	−0.0017 (8)	−0.0002 (10)
C4	0.0448 (11)	0.0511 (12)	0.0453 (12)	−0.0066 (9)	−0.0003 (9)	−0.0023 (10)
C9	0.0411 (10)	0.0502 (12)	0.0384 (11)	−0.0111 (9)	−0.0021 (8)	−0.0014 (9)
N1	0.0609 (13)	0.0696 (14)	0.0758 (15)	−0.0004 (10)	−0.0015 (11)	−0.0257 (13)
N2	0.0999 (18)	0.0699 (15)	0.0628 (14)	−0.0293 (13)	0.0150 (13)	0.0073 (12)
C12	0.0479 (11)	0.0463 (12)	0.0367 (11)	−0.0061 (9)	0.0003 (8)	−0.0033 (9)
C15	0.0646 (14)	0.0431 (12)	0.0517 (14)	−0.0139 (11)	0.0008 (11)	0.0007 (11)
C3	0.0706 (16)	0.0651 (16)	0.0538 (15)	0.0063 (13)	−0.0092 (12)	−0.0026 (12)
C11	0.0893 (18)	0.0542 (14)	0.0584 (15)	−0.0278 (13)	0.0043 (13)	−0.0119 (12)
C10	0.109 (2)	0.081 (2)	0.0601 (17)	−0.0354 (18)	0.0254 (16)	0.0058 (15)
C5	0.0591 (14)	0.0854 (19)	0.0571 (16)	0.0016 (14)	0.0114 (12)	−0.0041 (14)
C1	0.116 (3)	0.107 (3)	0.0429 (15)	−0.017 (2)	0.0079 (16)	0.0082 (17)
C6	0.088 (2)	0.130 (3)	0.0549 (18)	0.003 (2)	0.0176 (16)	−0.0021 (19)
C2	0.104 (2)	0.084 (2)	0.0641 (19)	0.0032 (18)	−0.0244 (17)	0.0116 (16)

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Geometric parameters (Å, °)

S1—C9	1.734 (2)	C12—H12	0.93
S1—C11	1.806 (2)	C3—C2	1.397 (4)
S2—C9	1.747 (2)	C3—H3	0.93
S2—C10	1.806 (3)	C11—H11A	0.96
C13—C12	1.352 (3)	C11—H11B	0.96
C13—C14	1.431 (3)	C11—H11C	0.96
C13—C15	1.443 (3)	C10—H10A	0.96
C8—C9	1.366 (3)	C10—H10B	0.96
C8—C12	1.439 (3)	C10—H10C	0.96
C8—C7	1.510 (3)	C5—C6	1.365 (4)
O1—C7	1.220 (3)	C5—H5	0.93
C14—N1	1.142 (3)	C1—C6	1.358 (5)
C7—C4	1.485 (3)	C1—C2	1.364 (5)
C4—C3	1.371 (3)	C1—H1	0.93
C4—C5	1.391 (3)	C6—H6	0.93
N2—C15	1.135 (3)	C2—H2	0.93

C9—S1—C11	104.55 (12)	S1—C11—H11A	109.5
C9—S2—C10	103.13 (13)	S1—C11—H11B	109.5
C12—C13—C14	124.00 (19)	H11A—C11—H11B	109.5
C12—C13—C15	120.4 (2)	S1—C11—H11C	109.5
C14—C13—C15	115.56 (19)	H11A—C11—H11C	109.5
C9—C8—C12	121.01 (19)	H11B—C11—H11C	109.5
C9—C8—C7	119.33 (18)	S2—C10—H10A	109.5
C12—C8—C7	119.26 (18)	S2—C10—H10B	109.5
N1—C14—C13	179.3 (2)	H10A—C10—H10B	109.5
O1—C7—C4	121.3 (2)	S2—C10—H10C	109.5
O1—C7—C8	118.9 (2)	H10A—C10—H10C	109.5
C4—C7—C8	119.80 (19)	H10B—C10—H10C	109.5
C3—C4—C5	119.8 (2)	C6—C5—C4	120.0 (3)
C3—C4—C7	122.3 (2)	C6—C5—H5	120.0
C5—C4—C7	117.9 (2)	C4—C5—H5	120.0
C8—C9—S1	120.97 (16)	C6—C1—C2	120.8 (3)
C8—C9—S2	118.70 (17)	C6—C1—H1	119.6
S1—C9—S2	120.31 (12)	C2—C1—H1	119.6
C13—C12—C8	127.4 (2)	C1—C6—C5	120.3 (3)
C13—C12—H12	116.3	C1—C6—H6	119.9
C8—C12—H12	116.3	C5—C6—H6	119.9
N2—C15—C13	178.5 (3)	C1—C2—C3	119.9 (3)
C4—C3—C2	119.3 (3)	C1—C2—H2	120.1
C4—C3—H3	120.4	C3—C2—H2	120.1
C2—C3—H3	120.4

C9—C8—C7—O1	−119.9 (2)	C10—S2—C9—C8	−129.17 (19)
C12—C8—C7—O1	53.0 (3)	C10—S2—C9—S1	51.99 (17)
C9—C8—C7—C4	61.1 (3)	C14—C13—C12—C8	6.1 (4)
C12—C8—C7—C4	−126.1 (2)	C15—C13—C12—C8	−174.6 (2)
O1—C7—C4—C3	−156.3 (2)	C9—C8—C12—C13	−167.0 (2)
C8—C7—C4—C3	22.7 (3)	C7—C8—C12—C13	20.3 (3)
O1—C7—C4—C5	22.0 (3)	C5—C4—C3—C2	1.2 (4)
C8—C7—C4—C5	−159.0 (2)	C7—C4—C3—C2	179.5 (2)
C12—C8—C9—S1	17.8 (3)	C3—C4—C5—C6	−2.8 (4)
C7—C8—C9—S1	−169.48 (15)	C7—C4—C5—C6	178.8 (3)
C12—C8—C9—S2	−161.03 (16)	C2—C1—C6—C5	0.5 (6)
C7—C8—C9—S2	11.7 (3)	C4—C5—C6—C1	2.0 (5)
C11—S1—C9—C8	−148.69 (19)	C6—C1—C2—C3	−2.1 (6)
C11—S1—C9—S2	30.13 (17)	C4—C3—C2—C1	1.2 (5)

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Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···S1	0.96	2.82	3.360 (3)	116
C12—H12···S1	0.93	2.66	3.040 (2)	105

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2822).

References

Anabha, E. R. & Asokan, C. V. (2006). Synthesis, pp. 151–155.
Dahne, S. (1978). Science, 199, 1163–1167. [DOI] [PubMed]
Dastidar, P., Guru Row, T. N. & Venkatesan, K. (1993). Acta Cryst. B49, 900–905.
Freier, T., Michalik, M. & Peseke, K. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 1265–1271.
Homrighausen, C. L. & Krause Bauer, J. A. (2004). Acta Cryst. E60, o1828–o1829.
Johnson, C. K. (1976). ORTEPII Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
MacScience (2002). XPRESS MacScience Co. Ltd, Yokohama, Japan.
Michalik, M., Freier, T., Reinke, H. & Peseke, K. (2002). J. Chem. Soc. Perkin Trans. 2, pp. 114–119.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024635/ci2822sup1.cif

e-65-o1727-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024635/ci2822Isup2.hkl

e-65-o1727-Isup2.hkl^{(138.3KB, hkl)}

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

[bb1] Anabha, E. R. & Asokan, C. V. (2006). Synthesis, pp. 151–155.

[bb2] Dahne, S. (1978). Science, 199, 1163–1167. [DOI] [PubMed]

[bb3] Dastidar, P., Guru Row, T. N. & Venkatesan, K. (1993). Acta Cryst. B49, 900–905.

[bb4] Freier, T., Michalik, M. & Peseke, K. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 1265–1271.

[bb5] Homrighausen, C. L. & Krause Bauer, J. A. (2004). Acta Cryst. E60, o1828–o1829.

[bb6] Johnson, C. K. (1976). ORTEPII Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.

[bb7] MacScience (2002). XPRESS MacScience Co. Ltd, Yokohama, Japan.

[bb8] Michalik, M., Freier, T., Reinke, H. & Peseke, K. (2002). J. Chem. Soc. Perkin Trans. 2, pp. 114–119.

[bb9] 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.

[bb10] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb11] Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

PERMALINK

2-[2-Benzoyl-3,3-bis(methylsulfanyl)prop-2-enylidene]malononitrile

Joseph Nirmala

N V Unnikrishnan

E R Anabha

C Sudarsanakumar

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Hydrogen-bond geometry (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

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

Atomic displacement parameters (Å²)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

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PERMALINK

2-[2-Benzoyl-3,3-bis­(methyl­sulfan­yl)prop-2-enyl­idene]malononitrile

Joseph Nirmala

N V Unnikrishnan

E R Anabha

C Sudarsanakumar

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Hydrogen-bond geometry (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

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

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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2-[2-Benzoyl-3,3-bis(methylsulfanyl)prop-2-enylidene]malononitrile

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

Atomic displacement parameters (Å²)