1,5-Bis(1-phenyl-ethyl-idene)thio-carbono-hydrazide.

The title mol-ecule, C(17)H(18)N(4)S, is not planar, as indicated by the dihedral angle of 27.24 (9)° between the two benzene rings. In the crystal, inter-molecular N-H⋯S hydrogen bonds link pairs of mol-ecules into inversion dimers.

Related literature

For the biological activity and catalytic abilities of Schiff base derivatives and complexes, see: Loncle et al. (2004 ▶); Camp et al. (2010 ▶). For a related structure, see: Meyers et al. (1995 ▶).

Experimental

Crystal data

C17H18N4S

M = 310.41

Triclinic,

a = 7.5947 (15) Å

b = 8.8202 (18) Å

c = 13.084 (3) Å

α = 76.62 (3)°

β = 76.39 (3)°

γ = 82.35 (3)°

V = 825.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.20 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.962, T max = 0.977

4272 measured reflections

2876 independent reflections

2033 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.146

S = 1.02

2876 reflections

202 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018320/vm2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018320/vm2088Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018320/vm2088Isup3.cml

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

C17H18N4S	Z = 2
Mr = 310.41	F(000) = 328
Triclinic, P1	Dx = 1.248 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5947 (15) Å	Cell parameters from 1351 reflections
b = 8.8202 (18) Å	θ = 2.6–25.1°
c = 13.084 (3) Å	µ = 0.20 mm−1
α = 76.62 (3)°	T = 293 K
β = 76.39 (3)°	Block, colourless
γ = 82.35 (3)°	0.20 × 0.16 × 0.12 mm
V = 825.8 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	2876 independent reflections
Radiation source: fine-focus sealed tube	2033 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.962, Tmax = 0.977	k = −10→9
4272 measured reflections	l = −15→15

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.0718P)2 + 0.2086P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2876 reflections	Δρmax = 0.24 e Å−3
202 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (4)

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.

	x	y	z	Uiso*/Ueq
S1	0.91194 (11)	0.69768 (7)	−0.10817 (5)	0.0688 (3)
N1	0.7946 (3)	0.9200 (2)	0.00704 (14)	0.0560 (6)
H1	0.7779	0.9500	0.0669	0.067*
N2	0.7386 (3)	1.0205 (2)	−0.07909 (14)	0.0521 (5)
N3	0.9241 (3)	0.6971 (2)	0.09311 (14)	0.0566 (6)
H3	0.9787	0.6046	0.0982	0.068*
N4	0.8830 (3)	0.7712 (2)	0.17832 (15)	0.0520 (5)
C1	0.8745 (3)	0.7765 (3)	−0.00005 (18)	0.0524 (6)
C2	0.6582 (3)	1.1530 (3)	−0.06107 (18)	0.0498 (6)
C3	0.6205 (4)	1.2028 (3)	0.0448 (2)	0.0677 (8)
H3A	0.6098	1.1120	0.1022	0.102*
H3B	0.5091	1.2689	0.0525	0.102*
H3C	0.7185	1.2592	0.0474	0.102*
C4	0.6017 (3)	1.2612 (2)	−0.15566 (18)	0.0514 (6)
C5	0.6339 (4)	1.2169 (3)	−0.25393 (19)	0.0617 (7)
H5	0.6893	1.1180	−0.2604	0.074*
C6	0.5846 (4)	1.3179 (3)	−0.3422 (2)	0.0701 (8)
H6	0.6078	1.2867	−0.4076	0.084*
C7	0.5015 (4)	1.4645 (3)	−0.3343 (2)	0.0704 (8)
H7	0.4694	1.5324	−0.3942	0.085*
C8	0.4666 (4)	1.5095 (3)	−0.2381 (2)	0.0748 (8)
H8	0.4092	1.6080	−0.2321	0.090*
C9	0.5164 (4)	1.4089 (3)	−0.1491 (2)	0.0661 (8)
H9	0.4921	1.4411	−0.0839	0.079*
C10	0.9131 (3)	0.6990 (3)	0.27089 (18)	0.0516 (6)
C11	0.9913 (4)	0.5327 (3)	0.2956 (2)	0.0708 (8)
H11A	0.9160	0.4657	0.2797	0.106*
H11B	0.9961	0.5032	0.3703	0.106*
H11C	1.1118	0.5228	0.2525	0.106*
C12	0.8641 (3)	0.7926 (3)	0.35463 (18)	0.0528 (6)
C13	0.8581 (5)	0.9550 (3)	0.3268 (2)	0.0790 (9)
H13	0.8894	1.0049	0.2550	0.095*
C14	0.8063 (7)	1.0415 (4)	0.4049 (3)	0.1186 (16)
H14	0.8012	1.1501	0.3855	0.142*
C15	0.7621 (7)	0.9703 (4)	0.5109 (3)	0.1202 (16)
H15	0.7270	1.0304	0.5631	0.144*
C16	0.7691 (5)	0.8118 (4)	0.5402 (2)	0.0960 (12)
H16	0.7384	0.7633	0.6124	0.115*
C17	0.8217 (4)	0.7239 (3)	0.4628 (2)	0.0696 (8)
H17	0.8291	0.6154	0.4834	0.084*

	U11	U22	U33	U12	U13	U23
S1	0.1111 (7)	0.0488 (4)	0.0460 (4)	0.0237 (4)	−0.0270 (4)	−0.0155 (3)
N1	0.0858 (16)	0.0416 (10)	0.0403 (10)	0.0161 (10)	−0.0229 (10)	−0.0105 (8)
N2	0.0758 (14)	0.0391 (10)	0.0407 (10)	0.0090 (9)	−0.0189 (9)	−0.0079 (8)
N3	0.0823 (15)	0.0436 (11)	0.0424 (11)	0.0156 (10)	−0.0214 (10)	−0.0092 (9)
N4	0.0683 (14)	0.0459 (11)	0.0418 (10)	0.0067 (9)	−0.0171 (9)	−0.0102 (8)
C1	0.0691 (17)	0.0430 (12)	0.0427 (13)	0.0073 (11)	−0.0156 (11)	−0.0071 (10)
C2	0.0654 (16)	0.0407 (12)	0.0446 (13)	0.0064 (11)	−0.0165 (11)	−0.0128 (10)
C3	0.097 (2)	0.0580 (15)	0.0537 (15)	0.0202 (14)	−0.0303 (15)	−0.0234 (12)
C4	0.0660 (16)	0.0410 (12)	0.0474 (13)	0.0063 (11)	−0.0176 (12)	−0.0103 (10)
C5	0.086 (2)	0.0492 (14)	0.0503 (14)	0.0137 (13)	−0.0234 (13)	−0.0130 (11)
C6	0.096 (2)	0.0658 (17)	0.0490 (14)	0.0156 (15)	−0.0264 (14)	−0.0144 (13)
C7	0.086 (2)	0.0609 (16)	0.0582 (17)	0.0102 (14)	−0.0271 (15)	0.0019 (13)
C8	0.103 (2)	0.0476 (14)	0.0700 (18)	0.0218 (15)	−0.0289 (16)	−0.0092 (13)
C9	0.094 (2)	0.0482 (14)	0.0533 (15)	0.0171 (13)	−0.0203 (14)	−0.0140 (12)
C10	0.0650 (16)	0.0453 (13)	0.0444 (13)	0.0039 (11)	−0.0194 (11)	−0.0058 (10)
C11	0.101 (2)	0.0559 (15)	0.0552 (15)	0.0207 (15)	−0.0320 (15)	−0.0116 (12)
C12	0.0649 (16)	0.0496 (13)	0.0446 (13)	0.0031 (11)	−0.0183 (11)	−0.0088 (11)
C13	0.132 (3)	0.0535 (16)	0.0543 (16)	0.0003 (16)	−0.0293 (17)	−0.0106 (13)
C14	0.230 (5)	0.0540 (18)	0.078 (2)	0.015 (2)	−0.049 (3)	−0.0248 (17)
C15	0.219 (5)	0.078 (2)	0.065 (2)	0.028 (3)	−0.036 (3)	−0.0342 (18)
C16	0.156 (3)	0.080 (2)	0.0468 (16)	0.014 (2)	−0.0207 (19)	−0.0171 (15)
C17	0.104 (2)	0.0558 (15)	0.0473 (15)	0.0050 (15)	−0.0223 (14)	−0.0075 (12)

S1—C1	1.667 (2)	C7—H7	0.9300
N1—C1	1.343 (3)	C8—C9	1.388 (3)
N1—N2	1.378 (2)	C8—H8	0.9300
N1—H1	0.8600	C9—H9	0.9300
N2—C2	1.290 (3)	C10—C12	1.471 (3)
N3—C1	1.367 (3)	C10—C11	1.499 (3)
N3—N4	1.374 (3)	C11—H11A	0.9600
N3—H3	0.8600	C11—H11B	0.9600
N4—C10	1.288 (3)	C11—H11C	0.9600
C2—C4	1.490 (3)	C12—C17	1.383 (3)
C2—C3	1.502 (3)	C12—C13	1.392 (3)
C3—H3A	0.9600	C13—C14	1.368 (4)
C3—H3B	0.9600	C13—H13	0.9300
C3—H3C	0.9600	C14—C15	1.366 (5)
C4—C5	1.387 (3)	C14—H14	0.9300
C4—C9	1.388 (3)	C15—C16	1.358 (5)
C5—C6	1.380 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.370 (4)
C6—C7	1.376 (4)	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.363 (4)
C1—N1—N2	121.73 (18)	C7—C8—H8	119.9
C1—N1—H1	119.1	C9—C8—H8	119.9
N2—N1—H1	119.1	C8—C9—C4	121.1 (2)
C2—N2—N1	115.81 (18)	C8—C9—H9	119.5
C1—N3—N4	117.21 (18)	C4—C9—H9	119.5
C1—N3—H3	121.4	N4—C10—C12	114.8 (2)
N4—N3—H3	121.4	N4—C10—C11	124.5 (2)
C10—N4—N3	120.56 (19)	C12—C10—C11	120.7 (2)
N1—C1—N3	112.62 (19)	C10—C11—H11A	109.5
N1—C1—S1	125.52 (17)	C10—C11—H11B	109.5
N3—C1—S1	121.86 (17)	H11A—C11—H11B	109.5
N2—C2—C4	114.99 (19)	C10—C11—H11C	109.5
N2—C2—C3	125.2 (2)	H11A—C11—H11C	109.5
C4—C2—C3	119.78 (19)	H11B—C11—H11C	109.5
C2—C3—H3A	109.5	C17—C12—C13	117.6 (2)
C2—C3—H3B	109.5	C17—C12—C10	121.9 (2)
H3A—C3—H3B	109.5	C13—C12—C10	120.5 (2)
C2—C3—H3C	109.5	C14—C13—C12	120.2 (3)
H3A—C3—H3C	109.5	C14—C13—H13	119.9
H3B—C3—H3C	109.5	C12—C13—H13	119.9
C5—C4—C9	117.8 (2)	C15—C14—C13	120.7 (3)
C5—C4—C2	120.7 (2)	C15—C14—H14	119.6
C9—C4—C2	121.6 (2)	C13—C14—H14	119.6
C6—C5—C4	120.8 (2)	C16—C15—C14	120.2 (3)
C6—C5—H5	119.6	C16—C15—H15	119.9
C4—C5—H5	119.6	C14—C15—H15	119.9
C7—C6—C5	120.6 (2)	C15—C16—C17	119.6 (3)
C7—C6—H6	119.7	C15—C16—H16	120.2
C5—C6—H6	119.7	C17—C16—H16	120.2
C8—C7—C6	119.5 (2)	C16—C17—C12	121.6 (3)
C8—C7—H7	120.2	C16—C17—H17	119.2
C6—C7—H7	120.2	C12—C17—H17	119.2
C7—C8—C9	120.2 (2)
C1—N1—N2—C2	177.7 (2)	C7—C8—C9—C4	−0.2 (5)
C1—N3—N4—C10	174.7 (2)	C5—C4—C9—C8	−0.6 (4)
N2—N1—C1—N3	178.3 (2)	C2—C4—C9—C8	179.1 (3)
N2—N1—C1—S1	−1.9 (4)	N3—N4—C10—C12	179.5 (2)
N4—N3—C1—N1	1.4 (3)	N3—N4—C10—C11	−0.6 (4)
N4—N3—C1—S1	−178.43 (18)	N4—C10—C12—C17	155.1 (3)
N1—N2—C2—C4	179.0 (2)	C11—C10—C12—C17	−24.8 (4)
N1—N2—C2—C3	−0.8 (4)	N4—C10—C12—C13	−24.6 (4)
N2—C2—C4—C5	0.8 (4)	C11—C10—C12—C13	155.6 (3)
C3—C2—C4—C5	−179.5 (2)	C17—C12—C13—C14	−1.9 (5)
N2—C2—C4—C9	−178.9 (3)	C10—C12—C13—C14	177.7 (3)
C3—C2—C4—C9	0.8 (4)	C12—C13—C14—C15	0.8 (6)
C9—C4—C5—C6	0.9 (4)	C13—C14—C15—C16	0.0 (7)
C2—C4—C5—C6	−178.8 (3)	C14—C15—C16—C17	0.3 (7)
C4—C5—C6—C7	−0.4 (5)	C15—C16—C17—C12	−1.5 (6)
C5—C6—C7—C8	−0.5 (5)	C13—C12—C17—C16	2.3 (5)
C6—C7—C8—C9	0.7 (5)	C10—C12—C17—C16	−177.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1i	0.86	2.67	3.515 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯S1i	0.86	2.67	3.515 (2)	169

Symmetry code: (i) .