(1E,2E)-2-Methyl-3-phenyl­acryl­aldehyde thio­semicarbazone

Mendoza-Meroño, R.; García-Granda, S.

doi:10.1107/S1600536812022386

organic compounds

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Volume 68| Part 6| June 2012| Page o1840

doi:10.1107/S1600536812022386

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(1E,2E)-2-Methyl-3-phenylacrylaldehyde thiosemicarbazone

Rafael Mendoza-Meroño ^a and Santiago García-Granda ^a ^*

^aDepartamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo – CINN, C/ Julián Clavería, 8, 33006 Oviedo, Spain
^*Correspondence e-mail: sgg@uniovi.es

(Received 9 May 2012; accepted 16 May 2012; online 23 May 2012)

In the crystal structure of the title compound, C₁₁H₁₃N₃S, molecules form centrosymmetric synthons with an R₂²(8) graph-set motif, linked by pairs of N—H⋯S hydrogen bonds. The synthons are connected through further N—H⋯S hydrogen bonds, extending the packing to form a two-dimensional network lying parallel to (001). In addition, C—H⋯π interactions are observed.

Related literature

For related compounds and their biological activity, see: Abid et al. (2008 ); Finkielsztein et al. (2008 ). For hydrogen bonding in thiosemicarbazones, see: Lima et al. (2002 ); Allen et al. (1997 ). For the use of resonance-induced hydrogen bonding in supramolecular chemistry, see: Kearney et al. (1998 ). For hydrogen-bond motifs, see Bernstein et al. (1995 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₁H₁₃N₃S
M_r = 219.30
Orthorhombic, P b c a
a = 10.9165 (5) Å
b = 7.8150 (3) Å
c = 28.0390 (14) Å
V = 2392.08 (19) Å³
Z = 8
Cu Kα radiation
μ = 2.17 mm⁻¹
T = 293 K
0.51 × 0.06 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.763, T_max = 1.000
6973 measured reflections
2241 independent reflections
1644 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.110
S = 1.04
2241 reflections
188 parameters
All H-atom parameters refined
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H11⋯S1ⁱ	0.89 (2)	2.49 (3)	3.359 (2)	167 (2)
N3—H12B⋯S1ⁱⁱ	0.85 (3)	2.55 (3)	3.386 (2)	169 (2)
C3—H3⋯Cg1ⁱⁱⁱ	0.96 (3)	2.89 (3)	3.812 (3)	161 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) -x+1, -y, -z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ), PLATON (Spek, 2009 ), PARST95 (Nardelli, 1995 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812022386/ff2068sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022386/ff2068Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022386/ff2068Isup3.cml

checkCIF report

Comment top

Thiosemicarbazones have been extensively studied due to their wide range of pharmacological activities, such as antituberculosis (Abid et al., 2008) and antiviral (Finkielsztein et al., 2008) activities. In this work we have synthesized and crystallized a new thiosemicarbazone (I). (Fig. 1)

The values of distances N(1)–N(2) length (1.381 (2) Å.) and the dihedral angle C(10)═N(1)—N(2)—C(11) (176.32 (2) °) are similar to those found in CSD (Allen, 2002) for thiosemicarbazone systems [selected 371 hits, distance mean N—N is 1.374 Å and dihedral angle mean is 178.21 °]. According to this value —NH—C(S)—NH—N= moiety is planar and form a delocalized system, which is typical for this type of structures.

In general the molecular crystals of thiosemicarbazones are formed by hydrogen bonds interaction through –NH-C(S)-NH-N= fragment, forming in many cases synthons.(Lima et al., 2002). Even though that C=S···H—N hydrogen bond is weaker than its C=O···H—N analogue, the effective electronegativity of S is increased by conjugative interactions between C=S and the lone pair of one or more N substituents this effect is called resonance-induced hydrogen bonding at sulfur acceptor (Allen et al. 1997). This properties have been widely exploited in supramolecular chemistry, where it has been used as a building block for anion receptors (Kearney et al., 1998).

Centrosymmetric synthons (R²₂(8)) (Bernstein et al., 1995) are connected through N—H···S hydrogen bond to extend packing along the a axis (Fig 2). Intermolecular C—H···π interactions are also present in the crystal and contribute to stabilize the packing along c axis. (Fig.3).

Related literature top

For related compounds and their biological activity, see: Abid et al. (2008); Finkielsztein et al. (2008). For hydrogen bonding in thiosemicarbazones, see: Lima et al. (2002); Allen et al. (1997). For the use of resonance-induced hydrogen bonding in supramolecular chemistry, see: Kearney et al. (1998). For hydrogen-bond motifs, see Bernstein et al. (1995). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

A solution of trans-alfa-methylzimaldehyde (1.4619 g, 0.01 mol) and thiosemicarbazide (0.9144 g 0.01 mol) in absolute methanol (50 ml) was refluxed for 3 h in the presence of p-toluenesulfonic acid as catalyst, with continuous stirring. On cooling to room temperature the precipitate was filtered off, washed with copious cold methanol and dried in air. White single crystals of compound (I) were obtained after recrystallization from a solution in methanol.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis CCD (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2009), PARST95 (Nardelli, 1995) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Principal hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) -x+1/2, y+1/2, z; (ii) -x+1, -y, -z]
	Fig. 3. View of C—H···π interactions.

(1E,2E)-2-Methyl-3-phenylacrylaldehyde thiosemicarbazone top

Crystal data top

C₁₁H₁₃N₃S	F(000) = 928
M_r = 219.30	D_x = 1.218 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1905 reflections
a = 10.9165 (5) Å	θ = 4.1–70.4°
b = 7.8150 (3) Å	µ = 2.17 mm⁻¹
c = 28.0390 (14) Å	T = 293 K
V = 2392.08 (19) Å³	Plates, white
Z = 8	0.51 × 0.06 × 0.04 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2241 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1644 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 10.2673 pixels mm^-1	θ_max = 70.5°, θ_min = 5.1°
ω scans	h = −9→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −9→8
T_min = 0.763, T_max = 1.000	l = −25→34
6973 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0544P)² + 0.029P] where P = (F_o² + 2F_c²)/3
2241 reflections	(Δ/σ)_max < 0.001
188 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₁H₁₃N₃S	V = 2392.08 (19) Å³
M_r = 219.30	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 10.9165 (5) Å	µ = 2.17 mm⁻¹
b = 7.8150 (3) Å	T = 293 K
c = 28.0390 (14) Å	0.51 × 0.06 × 0.04 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2241 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	1644 reflections with I > 2σ(I)
T_min = 0.763, T_max = 1.000	R_int = 0.037
6973 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.110	All H-atom parameters refined
S = 1.04	Δρ_max = 0.20 e Å⁻³
2241 reflections	Δρ_min = −0.15 e Å⁻³
188 parameters

Special details top

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2010), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.33592 (5)	0.16055 (7)	0.01929 (2)	0.0596 (2)
N2	0.37558 (17)	0.4229 (2)	−0.03717 (7)	0.0586 (5)
N1	0.44022 (15)	0.5101 (2)	−0.07187 (6)	0.0561 (4)
C11	0.41598 (18)	0.2686 (2)	−0.02261 (7)	0.0511 (5)
C7	0.4125 (2)	0.9191 (3)	−0.12626 (8)	0.0584 (5)
N3	0.51732 (19)	0.2120 (3)	−0.04238 (9)	0.0692 (6)
C10	0.4010 (2)	0.6596 (3)	−0.08224 (8)	0.0564 (5)
C8	0.46045 (18)	0.7642 (3)	−0.11791 (7)	0.0541 (5)
C6	0.4535 (2)	1.0540 (3)	−0.15896 (7)	0.0573 (5)
C5	0.3674 (3)	1.1629 (3)	−0.17910 (10)	0.0713 (6)
C1	0.5758 (2)	1.0833 (4)	−0.17014 (10)	0.0727 (7)
C9	0.5700 (3)	0.6891 (4)	−0.14221 (11)	0.0764 (7)
C4	0.4017 (3)	1.2909 (4)	−0.21045 (11)	0.0848 (8)
C3	0.5221 (3)	1.3141 (4)	−0.22186 (11)	0.0890 (9)
C2	0.6085 (3)	1.2116 (4)	−0.20136 (11)	0.0883 (9)
H11	0.311 (2)	0.471 (3)	−0.0232 (8)	0.067 (7)*
H12A	0.557 (2)	0.274 (3)	−0.0641 (10)	0.082 (8)*
H7	0.339 (2)	0.944 (3)	−0.1080 (9)	0.069 (7)*
H10	0.332 (2)	0.702 (3)	−0.0649 (8)	0.059 (6)*
H9C	0.641 (3)	0.715 (4)	−0.1228 (13)	0.114 (12)*
H5	0.285 (2)	1.146 (3)	−0.1724 (9)	0.081 (8)*
H9B	0.581 (2)	0.740 (3)	−0.1745 (11)	0.089 (8)*
H9A	0.562 (3)	0.579 (5)	−0.1461 (12)	0.125 (13)*
H1	0.635 (2)	1.014 (3)	−0.1560 (9)	0.076 (8)*
H2	0.690 (3)	1.220 (4)	−0.2086 (11)	0.100 (10)*
H12B	0.546 (3)	0.116 (4)	−0.0339 (9)	0.080 (8)*
H4	0.341 (2)	1.358 (4)	−0.2224 (10)	0.090 (9)*
H3	0.541 (3)	1.403 (4)	−0.2441 (11)	0.098 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0531 (3)	0.0536 (3)	0.0720 (4)	−0.0009 (2)	−0.0050 (3)	0.0083 (3)
N2	0.0521 (10)	0.0481 (9)	0.0756 (12)	0.0041 (8)	0.0070 (9)	0.0064 (9)
N1	0.0550 (9)	0.0481 (9)	0.0652 (10)	−0.0033 (8)	0.0018 (9)	0.0002 (8)
C11	0.0478 (10)	0.0436 (10)	0.0621 (12)	−0.0031 (8)	−0.0106 (10)	−0.0031 (9)
C7	0.0551 (12)	0.0570 (12)	0.0630 (13)	−0.0016 (10)	0.0047 (11)	0.0018 (10)
N3	0.0636 (12)	0.0543 (11)	0.0898 (15)	0.0106 (10)	0.0142 (11)	0.0096 (11)
C10	0.0531 (11)	0.0504 (11)	0.0656 (13)	0.0009 (10)	0.0041 (10)	0.0010 (10)
C8	0.0543 (11)	0.0526 (11)	0.0553 (11)	−0.0041 (9)	−0.0007 (9)	−0.0026 (10)
C6	0.0696 (13)	0.0494 (11)	0.0528 (11)	−0.0034 (10)	−0.0004 (10)	−0.0014 (9)
C5	0.0783 (16)	0.0580 (13)	0.0776 (16)	0.0026 (13)	−0.0002 (13)	0.0036 (12)
C1	0.0691 (15)	0.0744 (16)	0.0744 (15)	−0.0148 (13)	−0.0067 (13)	0.0121 (13)
C9	0.088 (2)	0.0678 (17)	0.0732 (17)	0.0101 (15)	0.0213 (16)	−0.0001 (14)
C4	0.109 (2)	0.0639 (15)	0.0818 (18)	0.0019 (16)	−0.0199 (18)	0.0136 (14)
C3	0.123 (3)	0.0752 (17)	0.0687 (16)	−0.0288 (18)	−0.0133 (17)	0.0170 (14)
C2	0.088 (2)	0.095 (2)	0.0817 (18)	−0.0314 (17)	0.0004 (17)	0.0151 (16)

Geometric parameters (Å, º) top

S1—C11	1.690 (2)	C6—C5	1.388 (3)
N2—C11	1.347 (3)	C6—C1	1.390 (3)
N2—N1	1.381 (2)	C5—C4	1.384 (4)
N2—H11	0.89 (2)	C5—H5	0.93 (3)
N1—C10	1.278 (3)	C1—C2	1.378 (4)
C11—N3	1.314 (3)	C1—H1	0.93 (3)
C7—C8	1.339 (3)	C9—H9C	0.97 (3)
C7—C6	1.467 (3)	C9—H9B	1.00 (3)
C7—H7	0.97 (2)	C9—H9A	0.87 (4)
N3—H12A	0.89 (3)	C4—C3	1.364 (5)
N3—H12B	0.85 (3)	C4—H4	0.91 (3)
C10—C8	1.446 (3)	C3—C2	1.365 (4)
C10—H10	0.96 (2)	C3—H3	0.96 (3)
C8—C9	1.497 (3)	C2—H2	0.92 (3)

C11—N2—N1	119.17 (18)	C4—C5—C6	121.2 (3)
C11—N2—H11	120.1 (15)	C4—C5—H5	119.7 (17)
N1—N2—H11	120.5 (15)	C6—C5—H5	119.1 (16)
C10—N1—N2	116.09 (17)	C2—C1—C6	120.8 (3)
N3—C11—N2	116.7 (2)	C2—C1—H1	120.9 (16)
N3—C11—S1	124.07 (17)	C6—C1—H1	118.3 (16)
N2—C11—S1	119.25 (16)	C8—C9—H9C	108 (2)
C8—C7—C6	129.7 (2)	C8—C9—H9B	110.5 (16)
C8—C7—H7	114.3 (14)	H9C—C9—H9B	109 (3)
C6—C7—H7	116.0 (14)	C8—C9—H9A	111 (2)
C11—N3—H12A	121.2 (17)	H9C—C9—H9A	111 (3)
C11—N3—H12B	119.2 (18)	H9B—C9—H9A	107 (3)
H12A—N3—H12B	120 (3)	C3—C4—C5	120.4 (3)
N1—C10—C8	121.6 (2)	C3—C4—H4	122.7 (18)
N1—C10—H10	117.6 (13)	C5—C4—H4	116.9 (18)
C8—C10—H10	120.7 (13)	C2—C3—C4	119.3 (3)
C7—C8—C10	117.15 (19)	C2—C3—H3	123.5 (18)
C7—C8—C9	126.0 (2)	C4—C3—H3	117.3 (18)
C10—C8—C9	116.9 (2)	C3—C2—C1	121.1 (3)
C5—C6—C1	117.2 (2)	C3—C2—H2	122.4 (19)
C5—C6—C7	119.2 (2)	C1—C2—H2	116 (2)
C1—C6—C7	123.5 (2)

C11—N2—N1—C10	−176.32 (19)	C8—C7—C6—C5	149.4 (2)
N1—N2—C11—N3	1.0 (3)	C8—C7—C6—C1	−32.5 (4)
N1—N2—C11—N3	1.0 (3)	C1—C6—C5—C4	2.4 (4)
N1—N2—C11—S1	−179.15 (14)	C7—C6—C5—C4	−179.4 (2)
N1—N2—C11—S1	−179.15 (14)	C5—C6—C1—C2	−2.3 (4)
N2—N1—C10—C8	179.95 (18)	C7—C6—C1—C2	179.6 (2)
C6—C7—C8—C10	178.3 (2)	C6—C5—C4—C3	−0.8 (4)
C6—C7—C8—C9	−1.8 (4)	C5—C4—C3—C2	−1.1 (5)
N1—C10—C8—C7	180.0 (2)	C4—C3—C2—C1	1.3 (5)
N1—C10—C8—C9	0.1 (3)	C6—C1—C2—C3	0.5 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H11···S1ⁱ	0.89 (2)	2.49 (3)	3.359 (2)	167 (2)
N3—H12B···S1ⁱⁱ	0.85 (3)	2.55 (3)	3.386 (2)	169 (2)
C3—H3···Cg1ⁱⁱⁱ	0.96 (3)	2.89 (3)	3.812 (3)	161 (3)

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1, −y, −z; (iii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃N₃S
M_r	219.30
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	10.9165 (5), 7.8150 (3), 28.0390 (14)
V (Å³)	2392.08 (19)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.17
Crystal size (mm)	0.51 × 0.06 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.763, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6973, 2241, 1644
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.04
No. of reflections	2241
No. of parameters	188
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999), PLATON (Spek, 2009), PARST95 (Nardelli, 1995) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H11···S1ⁱ	0.89 (2)	2.49 (3)	3.359 (2)	167 (2)
N3—H12B···S1ⁱⁱ	0.85 (3)	2.55 (3)	3.386 (2)	169 (2)
C3—H3···Cg1ⁱⁱⁱ	0.96 (3)	2.89 (3)	3.812 (3)	161 (3)

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1, −y, −z; (iii) −x+1, y−1/2, −z+1/2.

Acknowledgements

We acknowledge financial support by the Agencia Española de Cooperación Internacional y Desarrollo (AECID), FEDER funding and the Spanish MINECO (MAT2006–01997, MAT2010-15094 and the Factoría de Cristalización Consolider Ingenio 2010).

References

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