2-(1,2,3,4-Tetra-hydro-naphthalen-1-yl-idene)hydrazinecarbothio-amide.

The mol-ecular structure of the title compound, C(11)H(13)N(3)S, is not planar: the maximum deviation from the mean plane of the non-H atoms is 0.521 (2) Å for an aliphatic C atom, which corresponds to an envelope conformation for the non-aromatic ring. The hydrazinecarbothio-amide substituent and the benzene ring have maximum deviations from the mean planes through the non-H atoms of 0.0288 (16) and 0.0124 (27) Å, respectively, and the dihedral angle between the two planes is 8.84 (13)°. In the crystal, mol-ecules are linked into chains along [1[Formula: see text]0] by pairs of N-H⋯S hydrogen bonds between mol-ecules related by centres of symmetry.

Related literature

For the synthesis of the title compound and the pharmacological activity of ketonethio­semicrabazones, see: Thanigaimalai et al. (2011 ▶). For crystal structures of other thio­semicarbazone derivatives with pharmacological activity, see: Pederzolli et al. (2011 ▶); Bittencourt et al. (2012 ▶).

Experimental

Crystal data

C11H13N3S

M = 219.30

Monoclinic,

a = 15.4388 (11) Å

b = 5.5781 (3) Å

c = 26.338 (2) Å

β = 102.940 (6)°

V = 2210.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Stoe IPDS-1 diffractometer

7673 measured reflections

2402 independent reflections

2019 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.126

S = 1.08

2402 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: X-AREA (Stoe & Cie, 2008 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033302/fy2063sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033302/fy2063Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033302/fy2063Isup3.cml

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

C11H13N3S	Z = 8
Mr = 219.30	F(000) = 928
Monoclinic, C2/c	Dx = 1.318 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 15.4388 (11) Å	µ = 0.26 mm−1
b = 5.5781 (3) Å	T = 293 K
c = 26.338 (2) Å	Block, yellow
β = 102.940 (6)°	0.3 × 0.2 × 0.2 mm
V = 2210.6 (3) Å3

Stoe IPDS-1 diffractometer	2019 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Stoe IPDS-1	Rint = 0.043
Graphite monochromator	θmax = 27.0°, θmin = 3.4°
φ scans	h = −19→19
7673 measured reflections	k = −6→7
2402 independent reflections	l = −29→33

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.6719P] where P = (Fo2 + 2Fc2)/3
2402 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
C1	0.29958 (11)	0.7852 (3)	0.39372 (7)	0.0547 (4)
C2	0.21106 (12)	0.8320 (4)	0.40609 (8)	0.0651 (5)
H2A	0.2187	0.9398	0.4357	0.078*
H2B	0.1869	0.6825	0.4157	0.078*
C3	0.14622 (13)	0.9414 (4)	0.36024 (9)	0.0748 (6)
H3A	0.1336	0.8271	0.3318	0.090*
H3B	0.0909	0.9779	0.3702	0.090*
C4	0.18397 (16)	1.1667 (4)	0.34255 (10)	0.0803 (6)
H4A	0.1438	1.2255	0.3113	0.096*
H4B	0.1882	1.2883	0.3693	0.096*
C5	0.27389 (14)	1.1280 (3)	0.33150 (7)	0.0647 (5)
C6	0.30605 (19)	1.2810 (4)	0.29776 (9)	0.0837 (6)
H6	0.2709	1.4078	0.2821	0.100*
C7	0.3882 (2)	1.2473 (5)	0.28746 (10)	0.0920 (7)
H7	0.4087	1.3528	0.2654	0.110*
C8	0.43993 (17)	1.0605 (5)	0.30923 (10)	0.0881 (7)
H8	0.4950	1.0357	0.3013	0.106*
C9	0.41110 (15)	0.9082 (4)	0.34300 (9)	0.0761 (6)
H9	0.4472	0.7820	0.3581	0.091*
C10	0.32796 (12)	0.9407 (3)	0.35500 (7)	0.0583 (4)
N1	0.35565 (10)	0.6249 (3)	0.41497 (6)	0.0566 (4)
N2	0.33609 (9)	0.4805 (3)	0.45306 (6)	0.0580 (4)
H1N2	0.2861	0.4818	0.4646	0.070*
C11	0.39552 (11)	0.3092 (3)	0.47378 (7)	0.0540 (4)
N3	0.46628 (10)	0.2886 (3)	0.45383 (7)	0.0680 (5)
H1N3	0.5063	0.1731	0.4636	0.082*
H2N3	0.4719	0.4075	0.4323	0.082*
S1	0.37784 (3)	0.13624 (10)	0.52278 (2)	0.0675 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0598 (9)	0.0488 (9)	0.0579 (9)	0.0039 (7)	0.0182 (7)	0.0021 (7)
C2	0.0643 (10)	0.0616 (11)	0.0741 (12)	0.0111 (8)	0.0254 (9)	0.0117 (9)
C3	0.0649 (11)	0.0767 (13)	0.0823 (14)	0.0139 (10)	0.0152 (10)	0.0063 (11)
C4	0.0913 (14)	0.0677 (13)	0.0816 (14)	0.0220 (11)	0.0186 (11)	0.0137 (11)
C5	0.0867 (13)	0.0505 (10)	0.0566 (10)	0.0006 (9)	0.0153 (9)	0.0002 (8)
C6	0.1232 (19)	0.0616 (12)	0.0656 (12)	−0.0012 (12)	0.0197 (12)	0.0117 (10)
C7	0.128 (2)	0.0829 (16)	0.0730 (14)	−0.0202 (15)	0.0384 (14)	0.0123 (12)
C8	0.0951 (16)	0.0975 (17)	0.0812 (15)	−0.0122 (14)	0.0396 (13)	0.0123 (13)
C9	0.0788 (13)	0.0780 (14)	0.0779 (13)	0.0020 (10)	0.0310 (11)	0.0133 (11)
C10	0.0706 (10)	0.0515 (9)	0.0546 (9)	−0.0013 (8)	0.0178 (8)	0.0023 (8)
N1	0.0617 (8)	0.0545 (8)	0.0578 (8)	0.0057 (6)	0.0226 (6)	0.0075 (7)
N2	0.0561 (8)	0.0595 (9)	0.0641 (8)	0.0119 (6)	0.0257 (7)	0.0127 (7)
C11	0.0531 (8)	0.0519 (9)	0.0604 (10)	0.0071 (7)	0.0199 (7)	0.0017 (7)
N3	0.0628 (9)	0.0686 (10)	0.0820 (11)	0.0186 (7)	0.0362 (8)	0.0212 (8)
S1	0.0622 (3)	0.0737 (4)	0.0741 (3)	0.0200 (2)	0.0316 (2)	0.0242 (2)

C1—N1	1.282 (2)	C6—H6	0.9300
C1—C10	1.478 (2)	C7—C8	1.359 (4)
C1—C2	1.497 (2)	C7—H7	0.9300
C2—C3	1.514 (3)	C8—C9	1.374 (3)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—C10	1.401 (3)
C3—C4	1.503 (3)	C9—H9	0.9300
C3—H3A	0.9700	N1—N2	1.3722 (19)
C3—H3B	0.9700	N2—C11	1.352 (2)
C4—C5	1.497 (3)	N2—H1N2	0.8899
C4—H4A	0.9700	C11—N3	1.319 (2)
C4—H4B	0.9700	C11—S1	1.6818 (17)
C5—C10	1.393 (3)	N3—H1N3	0.8900
C5—C6	1.401 (3)	N3—H2N3	0.8900
C6—C7	1.368 (4)
N1—C1—C10	115.77 (15)	C7—C6—H6	119.4
N1—C1—C2	125.91 (16)	C5—C6—H6	119.4
C10—C1—C2	118.28 (15)	C8—C7—C6	120.3 (2)
C1—C2—C3	111.69 (16)	C8—C7—H7	119.8
C1—C2—H2A	109.3	C6—C7—H7	119.8
C3—C2—H2A	109.3	C7—C8—C9	120.1 (2)
C1—C2—H2B	109.3	C7—C8—H8	119.9
C3—C2—H2B	109.3	C9—C8—H8	119.9
H2A—C2—H2B	107.9	C8—C9—C10	120.8 (2)
C4—C3—C2	110.56 (19)	C8—C9—H9	119.6
C4—C3—H3A	109.5	C10—C9—H9	119.6
C2—C3—H3A	109.5	C5—C10—C9	119.00 (18)
C4—C3—H3B	109.5	C5—C10—C1	120.42 (16)
C2—C3—H3B	109.5	C9—C10—C1	120.53 (17)
H3A—C3—H3B	108.1	C1—N1—N2	119.39 (14)
C5—C4—C3	112.39 (17)	C11—N2—N1	118.00 (13)
C5—C4—H4A	109.1	C11—N2—H1N2	115.5
C3—C4—H4A	109.1	N1—N2—H1N2	126.4
C5—C4—H4B	109.1	N3—C11—N2	116.66 (15)
C3—C4—H4B	109.1	N3—C11—S1	123.15 (13)
H4A—C4—H4B	107.9	N2—C11—S1	120.19 (12)
C10—C5—C6	118.5 (2)	C11—N3—H1N3	122.2
C10—C5—C4	120.74 (17)	C11—N3—H2N3	113.4
C6—C5—C4	120.78 (19)	H1N3—N3—H2N3	124.3
C7—C6—C5	121.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1i	0.89	2.71	3.5606 (14)	161
N3—H1N3···S1ii	0.89	2.45	3.3351 (16)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1i	0.89	2.71	3.5606 (14)	161
N3—H1N3⋯S1ii	0.89	2.45	3.3351 (16)	171

Symmetry codes: (i) ; (ii) .