2-[2-(4-Methyl­benzo­yl)-3,3-bis­(methyl­sulfan­yl)prop-2-enyl­idene]malononitrile

Nirmala, J.; Unnikrishnan, N.V.; Asokan, C.V.; Anabha, E.R.; Sudarsanakumar, C.

doi:10.1107/S1600536808004054

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o592

doi:10.1107/S1600536808004054

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2-[2-(4-Methylbenzoyl)-3,3-bis(methylsulfanyl)prop-2-enylidene]malononitrile

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

^aSchool of Pure and Applied Physics, Mahatma Gandhi University, Kottayam, Kerala, India, and ^bSchool of Chemical Sciences, Mahatma Gandhi University, Kottayam, Kerala, India
^*Correspondence e-mail: csudarsan1@sify.com

(Received 25 November 2007; accepted 7 February 2008; online 15 February 2008)

The title compound, C₁₆H₁₄N₂OS₂, is an example of a push–pull butadiene in which the electron-releasing and electron-withdrawing attachments on either end of the butadiene chain enhance the conjugation in the system. The molecules are linked by intermolecular C—H⋯N interactions.

Related literature

For related literature, see: Anabha & Asokan (2006 ); Dahne (1978 ); Dastidar et al. (1993 ); Freier et al. (1999 ); Homrighausen & Krause Bauer (2004 ); Michalik et al. (2002 ).

Experimental

Crystal data

C₁₆H₁₄N₂OS₂
M_r = 314.41
Monoclinic, C 2
a = 16.6050 (13) Å
b = 10.760 (2) Å
c = 9.905 (2) Å
β = 110.09 (2)°
V = 1662.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 295 (2) K
0.25 × 0.25 × 0.20 mm

Data collection

MacScience DIPLabo 32001 diffractometer
Absorption correction: none
4433 measured reflections
2717 independent reflections
2583 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.156
S = 1.11
2717 reflections
194 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), with 1210 Friedel pairs
Flack parameter: 0.11 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯N2ⁱ	0.96	2.49	3.3871	155
Symmetry code: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z-1]$ .

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, 2003 ) and ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004054/pv2055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004054/pv2055Isup2.hkl

checkCIF report

Comment top

Due to the presence of electron releasing alkyl sulfanyl groups and electron withdrawing nitrile groups on the terminal carbon atoms of butadiene moiety, these molecules are considered as push pull butadienes. The push pull substitution alters the polyene state of the unsubstituted butadiene with balanced pi-charge distribution to a polymethine structure with alternating charge densities at the carbon atoms (Dahne, 1978). The title compound, (I), was synthesized and its crystal structure determination was carried out in order to elucidate the molecular conformation to understand the influence of aroyl groups on the stereochemistry of the butadiene molecule in continuation of research in the synthesis of pyridine derivatives (Anabha & Asokan, 2006). A perspective view of (I) is shown in Fig. 1. The crystal structure of (I) shows that the double bonds in the aroyl substituted butadiene are arranged in a transoid manner. Bond lengths C9—C10 and C13—C14 indicate their double bond character while C8—C9 is a single bond. Moreover, the double bonds C9—C10 and C13—C14 and shortening of C10—S2 bond length shows the electronic effects on the push pull system. 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 & Krause Bauer, 2004). The hydrogen-bond interactions of the type C—H···N stabilize the three dimensional structure along the ac plane (Fig. 2).

Related literature top

For related literature, see: Anabha & Asokan (2006); Dahne (1978); Dastidar et al. (1993); Freier et al. (1999); Homrighausen & Krause Bauer (2004); Michalik et al. (2002).

Experimental top

2-[3,3-Bis(methyl sulfanyl)-2-(4-methyl benzoyl)-2- propylidene] malononitrile was obtained by the Knoevenagel condensation reaction of 3,3-bis (methyl sulfanyl)-2-(4-methyl benzoyl)-acrylaldehyde (1.33 g., 5 mmol) with malononitrile (500 mg., 7.5 mmol) (Anabha et al., 2006). Single crystals suitable for X-ray diffraction studies were grown by slow evaporation using solutions containing chloroform and hexane in the ratio 1:2. Pale yellow coloured crystals were obtained after two days.

Computing details top

Data collection: XPRESS (Mac Science, 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, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. An ORTEPII (Johnson, 1976) view of (I) showing the atom-labeling scheme; displacement ellipsoids are drawn at 50% probability level.
	Fig. 2. A view of the unit cell packing of (I) showing intermolecular interactions in the ac plane.

2-[2-(4-Methylbenzoyl)-3,3-bis(methylsulfanyl)prop-2-enylidene]malononitrile top

Crystal data top

C₁₆H₁₄N₂OS₂	F(000) = 656
M_r = 314.41	D_x = 1.257 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: C 2y	Cell parameters from 4224 reflections
a = 16.6050 (13) Å	θ = 3.5–25.5°
b = 10.760 (2) Å	µ = 0.32 mm⁻¹
c = 9.905 (2) Å	T = 295 K
β = 110.09 (2)°	Block, pale yellow
V = 1662.0 (5) Å³	0.25 × 0.25 × 0.20 mm
Z = 4

Data collection top

MacScience DIPLabo 32001 diffractometer	2583 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.5°, θ_min = 3.5°
Detector resolution: 10.0 pixels mm^-1	h = −20→20
ω scans	k = −11→11
4433 measured reflections	l = −11→11
2717 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.1066P)² + 0.5386P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.156	(Δ/σ)_max < 0.001
S = 1.11	Δρ_max = 0.30 e Å⁻³
2717 reflections	Δρ_min = −0.28 e Å⁻³
194 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.015 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.11 (12)

Crystal data top

C₁₆H₁₄N₂OS₂	V = 1662.0 (5) Å³
M_r = 314.41	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 16.6050 (13) Å	µ = 0.32 mm⁻¹
b = 10.760 (2) Å	T = 295 K
c = 9.905 (2) Å	0.25 × 0.25 × 0.20 mm
β = 110.09 (2)°

Data collection top

MacScience DIPLabo 32001 diffractometer	2583 reflections with I > 2σ(I)
4433 measured reflections	R_int = 0.035
2717 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.156	Δρ_max = 0.30 e Å⁻³
S = 1.11	Δρ_min = −0.28 e Å⁻³
2717 reflections	Absolute structure: Flack (1983)
194 parameters	Absolute structure parameter: 0.11 (12)
1 restraint

Special details top

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
S1	0.33194 (6)	0.02065 (9)	0.76965 (9)	0.0543 (3)
S2	0.16024 (7)	−0.08895 (12)	0.75086 (11)	0.0689 (4)
C5	0.1681 (2)	−0.0204 (3)	1.1171 (4)	0.0458 (8)
C13	0.3562 (2)	0.0395 (4)	1.0845 (3)	0.0471 (7)
H13	0.3801	0.0925	1.0344	0.057*
C9	0.2833 (2)	−0.0289 (3)	0.9991 (3)	0.0430 (7)
C8	0.2276 (2)	−0.0956 (4)	1.0693 (3)	0.0471 (8)
C14	0.3959 (2)	0.0379 (4)	1.2301 (3)	0.0508 (8)
C10	0.2604 (2)	−0.0317 (3)	0.8523 (4)	0.0468 (7)
O1	0.2346 (2)	−0.2092 (3)	1.0871 (3)	0.0680 (8)
C4	0.1194 (3)	−0.0773 (4)	1.1895 (5)	0.0622 (10)
H4	0.1228	−0.1628	1.2041	0.075*
C6	0.1602 (3)	0.1060 (4)	1.0927 (5)	0.0592 (10)
H6	0.1916	0.1447	1.0428	0.071*
C16	0.4673 (2)	0.1193 (4)	1.2927 (4)	0.0553 (9)
C15	0.3732 (3)	−0.0373 (4)	1.3306 (4)	0.0588 (10)
C3	0.0660 (3)	−0.0065 (5)	1.2394 (5)	0.0716 (12)
H3	0.0341	−0.0452	1.2882	0.086*
C2	0.0592 (3)	0.1204 (6)	1.2184 (5)	0.0729 (13)
N1	0.3560 (3)	−0.0944 (5)	1.4132 (4)	0.0905 (14)
N2	0.5237 (3)	0.1858 (5)	1.3400 (5)	0.0795 (12)
C11	0.2658 (3)	0.1102 (5)	0.6206 (5)	0.0724 (12)
H11A	0.2391	0.0562	0.5405	0.109*
H11B	0.3003	0.1705	0.5942	0.109*
H11C	0.2223	0.1521	0.6470	0.109*
C12	0.1815 (4)	−0.1799 (6)	0.6150 (5)	0.0828 (15)
H12A	0.1970	−0.1258	0.5508	0.124*
H12B	0.1311	−0.2261	0.5620	0.124*
H12C	0.2278	−0.2364	0.6595	0.124*
C7	0.1061 (3)	0.1753 (5)	1.1419 (6)	0.0738 (13)
H7	0.1008	0.2602	1.1236	0.089*
C1	0.0013 (5)	0.2004 (8)	1.2746 (9)	0.105 (2)
H1A	−0.0539	0.1616	1.2510	0.157*
H1B	−0.0052	0.2812	1.2311	0.157*
H1C	0.0267	0.2085	1.3771	0.157*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0555 (5)	0.0664 (6)	0.0453 (5)	−0.0047 (4)	0.0227 (4)	−0.0002 (4)
S2	0.0532 (5)	0.0949 (9)	0.0551 (5)	−0.0188 (5)	0.0141 (4)	−0.0181 (5)
C5	0.0452 (17)	0.046 (2)	0.0481 (17)	−0.0059 (12)	0.0189 (14)	−0.0031 (13)
C13	0.0479 (16)	0.054 (2)	0.0413 (16)	−0.0045 (14)	0.0172 (13)	−0.0025 (13)
C9	0.0473 (17)	0.0434 (18)	0.0393 (15)	−0.0042 (12)	0.0162 (13)	−0.0027 (11)
C8	0.0526 (18)	0.049 (2)	0.0410 (16)	−0.0073 (14)	0.0176 (14)	−0.0026 (13)
C14	0.0494 (17)	0.063 (2)	0.0405 (15)	0.0010 (16)	0.0163 (13)	−0.0063 (15)
C10	0.0491 (18)	0.0487 (19)	0.0456 (17)	−0.0060 (13)	0.0202 (14)	−0.0053 (13)
O1	0.090 (2)	0.0475 (19)	0.081 (2)	−0.0027 (14)	0.0481 (17)	−0.0039 (13)
C4	0.062 (2)	0.062 (3)	0.072 (2)	0.0035 (18)	0.036 (2)	0.0115 (19)
C6	0.053 (2)	0.052 (3)	0.077 (3)	−0.0072 (15)	0.0284 (19)	−0.0051 (17)
C16	0.0472 (19)	0.071 (2)	0.0447 (18)	−0.0072 (17)	0.0118 (15)	−0.0098 (16)
C15	0.062 (2)	0.065 (3)	0.0454 (18)	−0.0017 (17)	0.0130 (16)	−0.0001 (17)
C3	0.069 (3)	0.076 (4)	0.085 (3)	0.0031 (19)	0.047 (2)	0.010 (2)
C2	0.052 (2)	0.090 (4)	0.079 (3)	−0.002 (2)	0.026 (2)	−0.024 (2)
N1	0.104 (3)	0.112 (4)	0.052 (2)	−0.021 (3)	0.023 (2)	0.015 (2)
N2	0.062 (2)	0.105 (4)	0.065 (2)	−0.020 (2)	0.0144 (19)	−0.016 (2)
C11	0.083 (3)	0.077 (3)	0.056 (2)	−0.003 (2)	0.024 (2)	0.016 (2)
C12	0.089 (3)	0.096 (4)	0.060 (3)	−0.033 (3)	0.022 (2)	−0.026 (2)
C7	0.071 (3)	0.052 (3)	0.107 (4)	−0.0002 (18)	0.041 (3)	−0.010 (2)
C1	0.090 (4)	0.104 (5)	0.140 (6)	−0.002 (3)	0.065 (4)	−0.036 (4)

Geometric parameters (Å, º) top

S1—C10	1.751 (3)	C6—H6	0.9300
S1—C11	1.790 (5)	C16—N2	1.142 (6)
S2—C10	1.734 (3)	C15—N1	1.135 (6)
S2—C12	1.795 (5)	C3—C2	1.381 (8)
C5—C6	1.379 (6)	C3—H3	0.9300
C5—C4	1.393 (5)	C2—C7	1.390 (7)
C5—C8	1.475 (5)	C2—C1	1.531 (7)
C13—C14	1.364 (5)	C11—H11A	0.9600
C13—C9	1.421 (5)	C11—H11B	0.9600
C13—H13	0.9300	C11—H11C	0.9600
C9—C10	1.372 (5)	C12—H12A	0.9600
C9—C8	1.515 (4)	C12—H12B	0.9600
C8—O1	1.235 (5)	C12—H12C	0.9600
C14—C15	1.430 (6)	C7—H7	0.9300
C14—C16	1.433 (5)	C1—H1A	0.9600
C4—C3	1.383 (6)	C1—H1B	0.9600
C4—H4	0.9300	C1—H1C	0.9600
C6—C7	1.380 (6)

C10—S1—C11	103.7 (2)	C2—C3—C4	121.4 (4)
C10—S2—C12	103.4 (2)	C2—C3—H3	119.3
C6—C5—C4	119.2 (4)	C4—C3—H3	119.3
C6—C5—C8	121.2 (3)	C3—C2—C7	118.0 (4)
C4—C5—C8	119.6 (3)	C3—C2—C1	122.0 (5)
C14—C13—C9	128.7 (3)	C7—C2—C1	119.9 (6)
C14—C13—H13	115.6	S1—C11—H11A	109.5
C9—C13—H13	115.6	S1—C11—H11B	109.5
C10—C9—C13	120.8 (3)	H11A—C11—H11B	109.5
C10—C9—C8	119.1 (3)	S1—C11—H11C	109.5
C13—C9—C8	120.1 (3)	H11A—C11—H11C	109.5
O1—C8—C5	122.6 (3)	H11B—C11—H11C	109.5
O1—C8—C9	119.4 (3)	S2—C12—H12A	109.5
C5—C8—C9	118.0 (3)	S2—C12—H12B	109.5
C13—C14—C15	126.6 (3)	H12A—C12—H12B	109.5
C13—C14—C16	118.5 (3)	S2—C12—H12C	109.5
C15—C14—C16	115.0 (3)	H12A—C12—H12C	109.5
C9—C10—S2	118.9 (3)	H12B—C12—H12C	109.5
C9—C10—S1	120.2 (3)	C6—C7—C2	121.2 (5)
S2—C10—S1	120.88 (19)	C6—C7—H7	119.4
C3—C4—C5	119.9 (4)	C2—C7—H7	119.4
C3—C4—H4	120.1	C2—C1—H1A	109.5
C5—C4—H4	120.1	C2—C1—H1B	109.5
C5—C6—C7	120.3 (4)	H1A—C1—H1B	109.5
C5—C6—H6	119.9	C2—C1—H1C	109.5
C7—C6—H6	119.9	H1A—C1—H1C	109.5
N2—C16—C14	178.5 (5)	H1B—C1—H1C	109.5
N1—C15—C14	178.0 (5)

C14—C13—C9—C10	−169.0 (4)	C8—C9—C10—S1	−169.0 (3)
C14—C13—C9—C8	13.6 (6)	C12—S2—C10—C9	−138.8 (3)
C6—C5—C8—O1	−178.5 (4)	C12—S2—C10—S1	40.6 (3)
C4—C5—C8—O1	2.1 (6)	C11—S1—C10—C9	−136.9 (3)
C6—C5—C8—C9	3.1 (5)	C11—S1—C10—S2	43.7 (3)
C4—C5—C8—C9	−176.3 (3)	C6—C5—C4—C3	−1.9 (6)
C10—C9—C8—O1	80.2 (5)	C8—C5—C4—C3	177.5 (4)
C13—C9—C8—O1	−102.4 (4)	C4—C5—C6—C7	1.3 (7)
C10—C9—C8—C5	−101.3 (4)	C8—C5—C6—C7	−178.1 (4)
C13—C9—C8—C5	76.1 (4)	C5—C4—C3—C2	0.5 (7)
C9—C13—C14—C15	1.7 (6)	C4—C3—C2—C7	1.6 (8)
C9—C13—C14—C16	−177.8 (4)	C4—C3—C2—C1	−179.2 (5)
C13—C9—C10—S2	−167.0 (3)	C5—C6—C7—C2	0.9 (8)
C8—C9—C10—S2	10.4 (5)	C3—C2—C7—C6	−2.3 (8)
C13—C9—C10—S1	13.6 (5)	C1—C2—C7—C6	178.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···N2ⁱ	0.96	2.49	3.3871	155

Symmetry code: (i) x−1/2, y−1/2, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂OS₂
M_r	314.41
Crystal system, space group	Monoclinic, C2
Temperature (K)	295
a, b, c (Å)	16.6050 (13), 10.760 (2), 9.905 (2)
β (°)	110.09 (2)
V (Å³)	1662.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.25 × 0.25 × 0.20

Data collection
Diffractometer	MacScience DIPLabo 32001 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4433, 2717, 2583
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.156, 1.11
No. of reflections	2717
No. of parameters	194
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.28
Absolute structure	Flack (1983)
Absolute structure parameter	0.11 (12)

Computer programs: XPRESS (Mac Science, 2002), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003) and ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···N2ⁱ	0.96	2.49	3.3871	155

Symmetry code: (i) x−1/2, y−1/2, z−1.

Acknowledgements

The authors acknowledge the National Single Crystal Diffractometer Facility, Department of Studies in Physics, University of Mysore, Manasagangothri, for help with the data collection. One of the authors (JN) is grateful to UGC, New Delhi, Government of India, for providing a teaching fellowship.

References

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Dastidar, P., Guru Row, T. N. & Venkatesan, K. (1993). Acta Cryst. B49, 900–905. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
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Volume 64| Part 3| March 2008| Page o592

doi:10.1107/S1600536808004054

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[2-(4-Methyl­benzo­yl)-3,3-bis­­(methyl­sulfan­yl)prop-2-enyl­­idene]malono­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[2-(4-Methylbenzoyl)-3,3-bis(methylsulfanyl)prop-2-enylidene]malononitrile