(E)-1-Phenyl-2-({5-[(1E)-(2-phenyl­hydrazin-1-yl­idene)meth­yl]-2-thien­yl}methyl­idene)hydrazine

Lima, G.M. de; Harrison, W.T.A.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536810003302

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o504-o505

doi:10.1107/S1600536810003302

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(E)-1-Phenyl-2-({5-[(1E)-(2-phenylhydrazin-1-ylidene)methyl]-2-thienyl}methylidene)hydrazine

Geraldo M. de Lima,^a William T. A. Harrison,^b Edward R. T. Tiekink,^c ^* James L. Wardell ^d ‡ and Solange M. S. V. Wardell ^e

^aDepartamento de Quimica, ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, and ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 26 January 2010; accepted 27 January 2010; online 3 February 2010)

The title molecule, C₁₈H₁₆N₄S, adopts a U-shape with the aromatic groups lying syn and orientated in the same direction as the thiophene S atom. The conformation about each of the C=N bonds is E. Overall, the molecule is curved as seen in the dihedral angle of 30.26 (19)° formed between the terminal benzene rings. In the crystal, supramolecular chains along the c axis are formed by a combination of N—H⋯N hydrogen bonds and N—H⋯π interactions.

Related literature

For specific uses of 2-substituted-thiophenes as materials, see: Michaleviciute et al. (2007 , 2009 ); Kwon et al. (2009 ). For their specific uses as biological agents, see: Sonar & Crooks (2009 ); Mellado & Cortes (2009 ); Satyanarayana et al. (2008 ); Lourenço et al. (2007 ). For the preparation of hydrazones of thiophenecarbaldehydes, see: Kwon, et al. (2009); Wardell et al. (2007 ); Vaysse & Pastour (1964 ); Novitskii et al. (1961 ). For related structures, see: Wardell et al. (2007, 2010 ); Ferreira et al. (2009 ); Nogueira et al. (2010 ); de Lima et al. (2010 ).

Experimental

Crystal data

C₁₈H₁₆N₄S
M_r = 320.41
Trigonal, P 3₂
a = 15.6495 (6) Å
c = 5.9335 (10) Å
V = 1258.5 (2) Å³
Z = 3
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 120 K
0.42 × 0.06 × 0.04 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.767, T_max = 1.000
11400 measured reflections
3675 independent reflections
3287 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.108
S = 1.04
3675 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1748 Friedel pairs
Flack parameter: 0.04 (10)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯N4ⁱ	0.88 (4)	2.58 (5)	3.398 (4)	155 (4)
C12—H12⋯N2ⁱⁱ	0.95	2.57	3.463 (5)	157
N4—H4N⋯Cgⁱⁱ	0.89 (4)	2.81 (5)	3.415 (4)	126 (3)
Symmetry codes: (i) $[-x+y+1, -x+2, z+{\script{1\over 3}}]$ ; (ii) $[-y+2, x-y+1, z+{\script{2\over 3}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003302/hg2637sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003302/hg2637Isup2.hkl

checkCIF report

Comment top

Hydrazone and amide derivatives of thiophene have found many uses, for example in optoelectronic application (Michaleviciute et al., 2007), as optical non-linear materials (Kwon et al., 2009), as hole transporting materials (Michaleviciute et al., 2009), and as biological agents (Sonar & Crooks, 2009; Mellado et al., 2009; Satyanarayana et al., 2008, Lourenço et al., 2007). In continuation of structural studies on thiophene derivatives (Wardell et al., 2007; Nogueira et al., 2010; Ferreira et al., 2009; Wardell et al., 2010; de Lima et al., 2010), we now report the structure of 2,5-thiophenedicarbaldehyde bis(phenylhydrazone), (I).

The molecule of (I) has a U-shaped conformation as the benzene rings are syn, lying to the same side of the molecule as the thiophene-S atom, Fig. 1. The conformation about each of the C5═N1 [1.282 (4) Å] and C12═N3 [1.287 (4) Å] double bonds is E. There are twists in the molecule, primarily about the hydrazine bonds, as seen in the values of the C5/N1/N2/C6 and C12/N3/N4/C13 torsion angles of -171.4 (3) and 165.1 (3) °. respectively. The dihedral angle formed between the two benzene rings is 30.26 (19) °.

Each of the hydrazine-N–H atoms participates in a significant intermolecular interactions to stabilise a supramolecular chain along the c axis, Fig. 2. The N2—H atom forms a conventional, albeit weak, N–H···N interaction, Table 1. The N4–H atom participates in a N–H···π interaction [N4–H···ring centroid(C6–C11)ⁱ distance = 2.81 (5) Å, N4···ring centroid(C6–C11)ⁱ = 3.415 (4) Å with an angle at H = 126 (3) ° for i: 2- y, 1+ x - y, 2/3+ z]. The resultant chain is further stabilised by C–H···N2 contacts, Table 1. The primary contacts between supramolecular chains are of the type C–H···π where the π-system is derived from the thiophene ring [C17–H···ring centroid(S1,C1–C4)ⁱⁱ = 2.87 Å, C17······ring centroid(S1,C1–C4)ⁱⁱ = 3.798 (6) Å, with angle at H = 165 ° for ii: 1-x+y, 1-x, -2/3+z], Fig. 3.

Related literature top

For specific uses of 2-substituted-thiophenes as materials, see: Michaleviciute et al. (2007, 2009); Kwon et al. (2009). For their specific uses as biological agents, see: Sonar & Crooks (2009); Mellado et al. (2009); Satyanarayana et al. (2008); Lourenço et al. (2007). For the preparation of hydrazones of thiophenecarbaldehydes, see: Kwon, et al. (2009); Wardell et al. (2007); Vaysse & Pastour (1964); Novitskii et al. (1961). For related structures, see: Wardell et al. (2007, 2010); Ferreira et al. (2009); Nogueira et al. (2010); de Lima et al. (2010).

Experimental top

Solutions of phenylhydrazine.hydrochloride (0.22 g, 2 mmol) in EtOH (10 ml) and 2,5-thiophenedicarbaldehyde (0.14 g, 1 mmol) in EtOH (10 ml) were mixed. The reaction mixture was refluxed for 1 h, and rotary evaporated. The solid residue was recrystallised twice from aq. EtOH (v;v 1:2), m.p. 498-500 K. lit value 504 K (Vaysse & Pastour 1964) and 483-484 K (Novitskii et al., 1961).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular chain in (I) mediated by N–H···N hydrogen bonds (blue dashed bonds) and N—H···π interactions (purple dashed lines). Hydrogen atoms not involved in these intermolecular interactions are omitted for reasons of clarity. Colour code: S, yellow; N, blue; C, grey; and H, green.
	Fig. 3. View in projection down the c axis of the unit cell contents for (I). Colour code: S, yellow; N, blue; C, grey; and H, green.

(E)-1-Phenyl-2-({5-[(1E)-(2-phenylhydrazin-1-ylidene)methyl]- 2-thienyl}methylidene)hydrazine top

Crystal data top

C₁₈H₁₆N₄S	D_x = 1.268 Mg m⁻³
M_r = 320.41	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3₂	Cell parameters from 8754 reflections
Hall symbol: P 32	θ = 2.9–27.5°
a = 15.6495 (6) Å	µ = 0.20 mm⁻¹
c = 5.9335 (10) Å	T = 120 K
V = 1258.5 (2) Å³	Rod, yellow
Z = 3	0.42 × 0.06 × 0.04 mm
F(000) = 504

Data collection top

Nonius KappaCCD area-detector diffractometer	3675 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	3287 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.059
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −20→20
T_min = 0.767, T_max = 1.000	l = −7→7
11400 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0104P)² + 1.4032P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3675 reflections	Δρ_max = 0.24 e Å⁻³
214 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1748 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (10)

Crystal data top

C₁₈H₁₆N₄S	Z = 3
M_r = 320.41	Mo Kα radiation
Trigonal, P3₂	µ = 0.20 mm⁻¹
a = 15.6495 (6) Å	T = 120 K
c = 5.9335 (10) Å	0.42 × 0.06 × 0.04 mm
V = 1258.5 (2) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	3675 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	3287 reflections with I > 2σ(I)
T_min = 0.767, T_max = 1.000	R_int = 0.059
11400 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	Δρ_max = 0.24 e Å⁻³
S = 1.04	Δρ_min = −0.22 e Å⁻³
3675 reflections	Absolute structure: Flack (1983), 1748 Friedel pairs
214 parameters	Absolute structure parameter: 0.04 (10)
1 restraint

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.81560 (6)	0.77053 (6)	0.68924 (12)	0.02814 (16)
N1	0.68935 (19)	0.86586 (19)	0.6256 (4)	0.0306 (6)
N2	0.6286 (2)	0.9036 (2)	0.5913 (5)	0.0333 (6)
H2N	0.614 (3)	0.927 (3)	0.711 (7)	0.050*
N3	0.89915 (18)	0.63239 (18)	0.6731 (4)	0.0297 (6)
N4	0.9375 (2)	0.5714 (2)	0.6555 (5)	0.0361 (6)
H4N	0.963 (3)	0.563 (3)	0.782 (7)	0.054*
C1	0.8031 (2)	0.8521 (2)	0.8654 (5)	0.0300 (7)
C2	0.8520 (2)	0.8645 (3)	1.0644 (5)	0.0346 (7)
H2	0.8543	0.9071	1.1812	0.041*
C3	0.8988 (2)	0.8076 (3)	1.0785 (5)	0.0351 (7)
H3	0.9360	0.8081	1.2055	0.042*
C4	0.8851 (2)	0.7513 (2)	0.8902 (5)	0.0268 (6)
C5	0.7407 (2)	0.8917 (2)	0.8070 (5)	0.0299 (6)
H5	0.7374	0.9380	0.9049	0.036*
C6	0.5620 (2)	0.8678 (2)	0.4142 (5)	0.0331 (7)
C7	0.4833 (3)	0.8868 (3)	0.4091 (6)	0.0389 (8)
H7	0.4741	0.9214	0.5294	0.047*
C8	0.4193 (3)	0.8546 (3)	0.2278 (6)	0.0471 (9)
H8	0.3660	0.8675	0.2242	0.056*
C9	0.4316 (3)	0.8040 (3)	0.0517 (6)	0.0488 (10)
H9	0.3871	0.7823	−0.0720	0.059*
C10	0.5088 (3)	0.7852 (3)	0.0562 (6)	0.0431 (8)
H10	0.5171	0.7502	−0.0647	0.052*
C11	0.5747 (3)	0.8169 (2)	0.2359 (5)	0.0360 (7)
H11	0.6279	0.8040	0.2374	0.043*
C12	0.9187 (2)	0.6824 (2)	0.8568 (5)	0.0299 (6)
H12	0.9559	0.6736	0.9714	0.036*
C13	0.9022 (3)	0.4977 (2)	0.4896 (5)	0.0345 (7)
C14	0.8457 (3)	0.4988 (2)	0.3078 (5)	0.0370 (7)
H14	0.8257	0.5468	0.2990	0.044*
C15	0.8196 (3)	0.4278 (3)	0.1403 (6)	0.0474 (9)
H15	0.7811	0.4276	0.0162	0.057*
C16	0.8481 (3)	0.3579 (3)	0.1506 (7)	0.0533 (11)
H16	0.8311	0.3110	0.0328	0.064*
C17	0.9020 (3)	0.3566 (3)	0.3340 (7)	0.0532 (11)
H17	0.9202	0.3072	0.3437	0.064*
C18	0.9296 (3)	0.4258 (2)	0.5029 (6)	0.0418 (8)
H18	0.9671	0.4246	0.6275	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0322 (4)	0.0288 (4)	0.0255 (3)	0.0168 (4)	0.0005 (3)	−0.0002 (3)
N1	0.0320 (14)	0.0295 (14)	0.0300 (13)	0.0151 (12)	0.0019 (11)	0.0043 (10)
N2	0.0406 (16)	0.0391 (16)	0.0295 (13)	0.0268 (14)	−0.0022 (12)	−0.0007 (11)
N3	0.0242 (13)	0.0246 (13)	0.0388 (14)	0.0111 (11)	0.0010 (11)	0.0006 (11)
N4	0.0395 (16)	0.0385 (17)	0.0379 (15)	0.0252 (14)	−0.0053 (12)	−0.0063 (12)
C1	0.0312 (17)	0.0308 (16)	0.0274 (14)	0.0150 (14)	0.0016 (12)	−0.0010 (12)
C2	0.0378 (18)	0.0400 (19)	0.0304 (16)	0.0228 (16)	−0.0030 (13)	−0.0084 (13)
C3	0.0350 (18)	0.044 (2)	0.0298 (16)	0.0226 (16)	−0.0032 (13)	−0.0057 (14)
C4	0.0230 (14)	0.0280 (15)	0.0272 (14)	0.0112 (12)	0.0024 (11)	0.0020 (12)
C5	0.0342 (17)	0.0300 (16)	0.0283 (15)	0.0182 (14)	0.0002 (12)	−0.0003 (12)
C6	0.0317 (17)	0.0304 (17)	0.0319 (16)	0.0115 (14)	0.0039 (13)	0.0095 (12)
C7	0.0340 (18)	0.044 (2)	0.0395 (18)	0.0198 (16)	0.0056 (14)	0.0091 (15)
C8	0.0309 (19)	0.052 (2)	0.052 (2)	0.0162 (17)	−0.0004 (16)	0.0148 (18)
C9	0.037 (2)	0.050 (2)	0.042 (2)	0.0083 (18)	−0.0089 (16)	0.0092 (17)
C10	0.040 (2)	0.038 (2)	0.0389 (19)	0.0102 (16)	0.0000 (15)	0.0029 (15)
C11	0.0335 (17)	0.0313 (17)	0.0378 (17)	0.0122 (15)	0.0025 (13)	0.0062 (13)
C12	0.0244 (15)	0.0318 (16)	0.0313 (15)	0.0124 (13)	0.0015 (12)	0.0031 (12)
C13	0.0378 (18)	0.0277 (16)	0.0346 (16)	0.0137 (14)	0.0059 (14)	−0.0012 (13)
C14	0.0415 (19)	0.0304 (18)	0.0357 (17)	0.0154 (16)	−0.0010 (14)	−0.0015 (13)
C15	0.050 (2)	0.041 (2)	0.0405 (19)	0.0145 (19)	−0.0006 (17)	−0.0031 (16)
C16	0.069 (3)	0.033 (2)	0.050 (2)	0.020 (2)	0.002 (2)	−0.0097 (17)
C17	0.074 (3)	0.033 (2)	0.056 (2)	0.029 (2)	0.006 (2)	−0.0014 (17)
C18	0.056 (2)	0.0297 (17)	0.0424 (19)	0.0239 (17)	−0.0019 (17)	−0.0025 (15)

Geometric parameters (Å, º) top

S1—C4	1.738 (3)	C7—H7	0.9500
S1—C1	1.736 (3)	C8—C9	1.382 (6)
N1—C5	1.282 (4)	C8—H8	0.9500
N1—N2	1.361 (4)	C9—C10	1.379 (5)
N2—C6	1.386 (4)	C9—H9	0.9500
N2—H2N	0.88 (4)	C10—C11	1.391 (5)
N3—C12	1.287 (4)	C10—H10	0.9500
N3—N4	1.362 (4)	C11—H11	0.9500
N4—C13	1.402 (4)	C12—H12	0.9500
N4—H4N	0.89 (4)	C13—C18	1.392 (5)
C1—C2	1.368 (4)	C13—C14	1.400 (5)
C1—C5	1.436 (4)	C14—C15	1.391 (5)
C2—C3	1.410 (5)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.374 (6)
C3—C4	1.371 (4)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.383 (6)
C4—C12	1.431 (4)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.377 (5)
C6—C11	1.396 (5)	C17—H17	0.9500
C6—C7	1.405 (5)	C18—H18	0.9500
C7—C8	1.382 (5)

C4—S1—C1	91.41 (15)	C9—C8—H8	119.6
C5—N1—N2	116.9 (3)	C10—C9—C8	119.8 (3)
N1—N2—C6	119.0 (3)	C10—C9—H9	120.1
N1—N2—H2N	116 (3)	C8—C9—H9	120.1
C6—N2—H2N	119 (3)	C9—C10—C11	120.7 (4)
C12—N3—N4	115.9 (3)	C9—C10—H10	119.6
N3—N4—C13	120.0 (3)	C11—C10—H10	119.6
N3—N4—H4N	115 (3)	C10—C11—C6	119.6 (3)
C13—N4—H4N	119 (3)	C10—C11—H11	120.2
C2—C1—C5	126.9 (3)	C6—C11—H11	120.2
C2—C1—S1	111.3 (2)	N3—C12—C4	120.7 (3)
C5—C1—S1	121.6 (2)	N3—C12—H12	119.6
C1—C2—C3	113.1 (3)	C4—C12—H12	119.6
C1—C2—H2	123.5	C18—C13—C14	120.3 (3)
C3—C2—H2	123.5	C18—C13—N4	118.1 (3)
C4—C3—C2	113.2 (3)	C14—C13—N4	121.5 (3)
C4—C3—H3	123.4	C15—C14—C13	118.4 (3)
C2—C3—H3	123.4	C15—C14—H14	120.8
C3—C4—C12	126.7 (3)	C13—C14—H14	120.8
C3—C4—S1	111.0 (2)	C16—C15—C14	121.4 (4)
C12—C4—S1	122.2 (2)	C16—C15—H15	119.3
N1—C5—C1	121.4 (3)	C14—C15—H15	119.3
N1—C5—H5	119.3	C15—C16—C17	119.3 (4)
C1—C5—H5	119.3	C15—C16—H16	120.3
N2—C6—C11	120.8 (3)	C17—C16—H16	120.3
N2—C6—C7	119.5 (3)	C18—C17—C16	121.0 (4)
C11—C6—C7	119.6 (3)	C18—C17—H17	119.5
C8—C7—C6	119.5 (4)	C16—C17—H17	119.5
C8—C7—H7	120.2	C17—C18—C13	119.5 (4)
C6—C7—H7	120.2	C17—C18—H18	120.3
C7—C8—C9	120.9 (4)	C13—C18—H18	120.3
C7—C8—H8	119.6

C5—N1—N2—C6	−171.4 (3)	C7—C8—C9—C10	0.0 (5)
C12—N3—N4—C13	165.1 (3)	C8—C9—C10—C11	−0.2 (5)
C4—S1—C1—C2	1.3 (3)	C9—C10—C11—C6	0.4 (5)
C4—S1—C1—C5	−173.5 (3)	N2—C6—C11—C10	−177.5 (3)
C5—C1—C2—C3	173.6 (3)	C7—C6—C11—C10	−0.3 (5)
S1—C1—C2—C3	−0.9 (4)	N4—N3—C12—C4	177.9 (3)
C1—C2—C3—C4	−0.3 (4)	C3—C4—C12—N3	178.5 (3)
C2—C3—C4—C12	−176.8 (3)	S1—C4—C12—N3	0.7 (4)
C2—C3—C4—S1	1.3 (4)	N3—N4—C13—C18	−168.3 (3)
C1—S1—C4—C3	−1.5 (3)	N3—N4—C13—C14	15.3 (5)
C1—S1—C4—C12	176.7 (3)	C18—C13—C14—C15	−1.2 (5)
N2—N1—C5—C1	176.6 (3)	N4—C13—C14—C15	175.2 (3)
C2—C1—C5—N1	−171.7 (3)	C13—C14—C15—C16	−0.1 (6)
S1—C1—C5—N1	2.2 (4)	C14—C15—C16—C17	1.6 (6)
N1—N2—C6—C11	−18.7 (4)	C15—C16—C17—C18	−1.8 (7)
N1—N2—C6—C7	164.1 (3)	C16—C17—C18—C13	0.5 (6)
N2—C6—C7—C8	177.3 (3)	C14—C13—C18—C17	1.0 (5)
C11—C6—C7—C8	0.1 (5)	N4—C13—C18—C17	−175.5 (3)
C6—C7—C8—C9	0.0 (5)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···N4ⁱ	0.88 (4)	2.58 (5)	3.398 (4)	155 (4)
C12—H12···N2ⁱⁱ	0.95	2.57	3.463 (5)	157
N4—H4N···Cgⁱⁱ	0.89 (4)	2.81 (5)	3.415 (4)	126 (3)

Symmetry codes: (i) −x+y+1, −x+2, z+1/3; (ii) −y+2, x−y+1, z+2/3.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₄S
M_r	320.41
Crystal system, space group	Trigonal, P3₂
Temperature (K)	120
a, c (Å)	15.6495 (6), 5.9335 (10)
V (Å³)	1258.5 (2)
Z	3
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.42 × 0.06 × 0.04

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.767, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11400, 3675, 3287
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.108, 1.04
No. of reflections	3675
No. of parameters	214
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22
Absolute structure	Flack (1983), 1748 Friedel pairs
Absolute structure parameter	0.04 (10)

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···N4ⁱ	0.88 (4)	2.58 (5)	3.398 (4)	155 (4)
C12—H12···N2ⁱⁱ	0.95	2.57	3.463 (5)	157
N4—H4N···Cgⁱⁱ	0.89 (4)	2.81 (5)	3.415 (4)	126 (3)

Symmetry codes: (i) −x+y+1, −x+2, z+1/3; (ii) −y+2, x−y+1, z+2/3.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

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Volume 66| Part 3| March 2010| Pages o504-o505

doi:10.1107/S1600536810003302

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

(E)-1-Phenyl-2-({5-[(1E)-(2-phenyl­hydrazin-1-yl­­idene)meth­yl]-2-thien­yl}methyl­­idene)hydrazine

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(E)-1-Phenyl-2-({5-[(1E)-(2-phenylhydrazin-1-ylidene)methyl]-2-thienyl}methylidene)hydrazine