(E)-1-Phenyl-2-({5-[(1E)-(2-phenyl-hydrazin-1-yl-idene)meth-yl]-2-thien-yl}methyl-idene)hydrazine.

The title mol-ecule, C(18)H(16)N(4)S, adopts a U-shape with the aromatic groups lying syn and orientated in the same direction as the thio-phene S atom. The conformation about each of the C=N bonds is E. Overall, the mol-ecule is curved as seen in the dihedral angle of 30.26 (19)° formed between the terminal benzene rings. In the crystal, supra-molecular chains along the c axis are formed by a combination of N-H⋯N hydrogen bonds and N-H⋯π inter-actions.

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 = 320.41

Trigonal,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.108

S = 1.04

3675 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1748 Friedel pairs

Flack parameter: 0.04 (10)

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 ▶).

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

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

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

C18H16N4S	Dx = 1.268 Mg m−3
Mr = 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

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	Rint = 0.059
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −20→20
Tmin = 0.767, Tmax = 1.000	l = −7→7
11400 measured reflections

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(Fo2) + (0.0104P)2 + 1.4032P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3675 reflections	Δρmax = 0.24 e Å−3
214 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 1748 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (10)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) .