N-Phenyl-2-(1,2,3,4-tetra-hydro-naph-thalen-1-yl-idene)hydrazinecarbo-thio-amide.

The conformation of the title mol-ecule, C17H17N3S, is stabilized by an intra-molecular N-H⋯N hydrogen bond involving the azometinic group. The dihedral angle between the two aromatic rings is 36.49 (06)°. The non-aromatic ring of the tetra-lone substituent adopts a sofa conformation. In the crystal, mol-ecules are linked by pairs of N-H⋯S hydrogen bonds related via centres of symmetry, forming dimers.

Related literature

For the synthesis and pharmacological activity of ketone­thio­semicarbazones, see: Thanigaimalai et al. (2011 ▶). For one of the first reports of the synthesis of thio­semicarbazone derivatives, see: Freund & Schander (1902 ▶). For the synthesis and crystal structure of 2-(1,2,3,4-tetra­hydro­naphthalen-1-yl­idene)hydrazinecarbo­thio­amide, see: de Oliveira et al. (2012 ▶).

Experimental

Crystal data

C17H17N3S

M = 295.40

Monoclinic,

a = 8.4415 (3) Å

b = 18.0256 (7) Å

c = 10.0260 (3) Å

β = 107.495 (2)°

V = 1455.02 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 200 K

0.3 × 0.3 × 0.2 mm

Data collection

Stoe IPDS-1 diffractometer

23139 measured reflections

3520 independent reflections

3045 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.089

S = 1.05

3520 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 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: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001585/bt6959sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001585/bt6959Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001585/bt6959Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H17N3S	F(000) = 624
Mr = 295.40	Dx = 1.348 Mg m−3
Monoclinic, P21/n	Melting point: 452 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.4415 (3) Å	Cell parameters from 26099 reflections
b = 18.0256 (7) Å	θ = 2.3–28.1°
c = 10.0260 (3) Å	µ = 0.22 mm−1
β = 107.495 (2)°	T = 200 K
V = 1455.02 (9) Å3	Cubic, yellow
Z = 4	0.3 × 0.3 × 0.2 mm

Stoe IPDS-1 diffractometer	3045 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Stoe IPDS-1	Rint = 0.069
Graphite monochromator	θmax = 28.1°, θmin = 2.3°
φ scans	h = −11→11
23139 measured reflections	k = −23→23
3520 independent reflections	l = −13→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0371P)2 + 0.419P] where P = (Fo2 + 2Fc2)/3
3520 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 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
S1	0.37784 (5)	0.09351 (2)	0.54195 (3)	0.03751 (11)
C1	0.47689 (15)	0.07366 (7)	0.70981 (13)	0.0270 (3)
N1	0.55649 (13)	0.00734 (6)	0.74440 (11)	0.0284 (2)
H1N	0.5703	−0.0195	0.6754	0.034*
N2	0.65846 (13)	−0.00109 (6)	0.88038 (11)	0.0278 (2)
C2	0.74837 (15)	−0.06010 (7)	0.91151 (12)	0.0250 (2)
C3	0.74732 (17)	−0.12214 (7)	0.81071 (13)	0.0291 (3)
H3A	0.8085	−0.1061	0.7455	0.035*
H3B	0.6312	−0.1327	0.7549	0.035*
C4	0.82614 (18)	−0.19283 (7)	0.88489 (14)	0.0328 (3)
H4A	0.7561	−0.2134	0.9394	0.039*
H4B	0.8337	−0.2303	0.8149	0.039*
C5	0.99852 (18)	−0.17606 (8)	0.98201 (15)	0.0363 (3)
H5A	1.0483	−0.2220	1.0311	0.044*
H5B	1.0702	−0.1583	0.9265	0.044*
C6	0.99093 (16)	−0.11786 (7)	1.08793 (14)	0.0286 (3)
C7	1.10660 (17)	−0.11733 (8)	1.22097 (15)	0.0351 (3)
H7	1.1929	−0.1532	1.2435	0.042*
C8	1.09825 (18)	−0.06577 (8)	1.32042 (15)	0.0383 (3)
H8	1.1796	−0.0657	1.4097	0.046*
C9	0.9709 (2)	−0.01430 (8)	1.28947 (14)	0.0382 (3)
H9	0.9627	0.0203	1.3585	0.046*
C10	0.85514 (18)	−0.01313 (7)	1.15781 (14)	0.0332 (3)
H10	0.7684	0.0226	1.1370	0.040*
C11	0.86494 (15)	−0.06406 (7)	1.05523 (12)	0.0262 (3)
N3	0.48970 (14)	0.11902 (6)	0.81878 (11)	0.0290 (2)
H2N	0.5513	0.1028	0.9008	0.035*
C12	0.41601 (15)	0.18985 (7)	0.81780 (12)	0.0255 (2)
C13	0.51258 (16)	0.24662 (8)	0.89485 (13)	0.0303 (3)
H13	0.6266	0.2382	0.9427	0.036*
C14	0.44270 (18)	0.31549 (8)	0.90199 (14)	0.0341 (3)
H14	0.5089	0.3542	0.9551	0.041*
C15	0.27640 (18)	0.32813 (8)	0.83178 (14)	0.0339 (3)
H15	0.2284	0.3754	0.8362	0.041*
C16	0.18101 (16)	0.27136 (8)	0.75537 (14)	0.0323 (3)
H16	0.0671	0.2799	0.7071	0.039*
C17	0.24953 (16)	0.20221 (7)	0.74832 (13)	0.0286 (3)
H17	0.1828	0.1634	0.6961	0.034*

	U11	U22	U33	U12	U13	U23
S1	0.0426 (2)	0.0436 (2)	0.02103 (15)	0.01742 (15)	0.00155 (13)	−0.00099 (13)
C1	0.0239 (6)	0.0313 (6)	0.0248 (6)	0.0019 (5)	0.0060 (5)	0.0000 (5)
N1	0.0290 (5)	0.0306 (6)	0.0223 (5)	0.0048 (4)	0.0029 (4)	−0.0006 (4)
N2	0.0277 (5)	0.0311 (6)	0.0223 (5)	0.0017 (4)	0.0040 (4)	0.0024 (4)
C2	0.0243 (6)	0.0258 (6)	0.0246 (6)	−0.0015 (5)	0.0070 (5)	0.0022 (4)
C3	0.0313 (6)	0.0284 (6)	0.0261 (6)	−0.0019 (5)	0.0066 (5)	−0.0003 (5)
C4	0.0397 (7)	0.0266 (6)	0.0331 (7)	0.0021 (5)	0.0125 (6)	−0.0002 (5)
C5	0.0343 (7)	0.0360 (7)	0.0395 (7)	0.0090 (6)	0.0127 (6)	0.0045 (6)
C6	0.0252 (6)	0.0289 (6)	0.0315 (6)	−0.0017 (5)	0.0082 (5)	0.0069 (5)
C7	0.0254 (6)	0.0386 (7)	0.0377 (7)	−0.0014 (5)	0.0038 (5)	0.0131 (6)
C8	0.0364 (7)	0.0414 (8)	0.0292 (6)	−0.0121 (6)	−0.0020 (5)	0.0101 (6)
C9	0.0509 (9)	0.0318 (7)	0.0266 (6)	−0.0076 (6)	0.0037 (6)	0.0003 (5)
C10	0.0405 (7)	0.0268 (7)	0.0288 (6)	0.0009 (5)	0.0050 (5)	0.0019 (5)
C11	0.0263 (6)	0.0255 (6)	0.0254 (6)	−0.0027 (5)	0.0058 (5)	0.0044 (4)
N3	0.0294 (5)	0.0337 (6)	0.0202 (5)	0.0072 (4)	0.0019 (4)	0.0002 (4)
C12	0.0263 (6)	0.0297 (6)	0.0205 (5)	0.0030 (5)	0.0069 (4)	0.0008 (4)
C13	0.0248 (6)	0.0391 (7)	0.0242 (6)	−0.0001 (5)	0.0033 (5)	−0.0019 (5)
C14	0.0360 (7)	0.0323 (7)	0.0310 (6)	−0.0038 (5)	0.0057 (5)	−0.0058 (5)
C15	0.0383 (7)	0.0303 (7)	0.0318 (7)	0.0055 (5)	0.0086 (6)	−0.0012 (5)
C16	0.0263 (6)	0.0388 (7)	0.0292 (6)	0.0054 (5)	0.0044 (5)	−0.0012 (5)
C17	0.0255 (6)	0.0323 (7)	0.0266 (6)	−0.0014 (5)	0.0058 (5)	−0.0036 (5)

S1—C1	1.6773 (13)	C7—H7	0.9500
C1—N3	1.3427 (16)	C8—C9	1.383 (2)
C1—N1	1.3642 (16)	C8—H8	0.9500
N1—N2	1.3846 (14)	C9—C10	1.3864 (19)
N1—H1N	0.8800	C9—H9	0.9500
N2—C2	1.2894 (16)	C10—C11	1.3995 (18)
C2—C11	1.4823 (16)	C10—H10	0.9500
C2—C3	1.5055 (18)	N3—C12	1.4190 (16)
C3—C4	1.5238 (18)	N3—H2N	0.8800
C3—H3A	0.9900	C12—C17	1.3861 (18)
C3—H3B	0.9900	C12—C13	1.3892 (18)
C4—C5	1.518 (2)	C13—C14	1.3854 (19)
C4—H4A	0.9900	C13—H13	0.9500
C4—H4B	0.9900	C14—C15	1.387 (2)
C5—C6	1.508 (2)	C14—H14	0.9500
C5—H5A	0.9900	C15—C16	1.3826 (19)
C5—H5B	0.9900	C15—H15	0.9500
C6—C7	1.3963 (18)	C16—C17	1.3849 (19)
C6—C11	1.4033 (18)	C16—H16	0.9500
C7—C8	1.380 (2)	C17—H17	0.9500
N3—C1—N1	114.44 (11)	C7—C8—C9	119.65 (13)
N3—C1—S1	125.48 (10)	C7—C8—H8	120.2
N1—C1—S1	120.06 (9)	C9—C8—H8	120.2
C1—N1—N2	117.35 (10)	C8—C9—C10	120.11 (14)
C1—N1—H1N	116.9	C8—C9—H9	119.9
N2—N1—H1N	121.6	C10—C9—H9	119.9
C2—N2—N1	118.38 (11)	C9—C10—C11	120.61 (13)
N2—C2—C11	116.45 (11)	C9—C10—H10	119.7
N2—C2—C3	124.48 (11)	C11—C10—H10	119.7
C11—C2—C3	119.01 (11)	C10—C11—C6	119.32 (12)
C2—C3—C4	112.33 (10)	C10—C11—C2	120.94 (11)
C2—C3—H3A	109.1	C6—C11—C2	119.70 (11)
C4—C3—H3A	109.1	C1—N3—C12	127.91 (11)
C2—C3—H3B	109.1	C1—N3—H2N	116.0
C4—C3—H3B	109.1	C12—N3—H2N	116.0
H3A—C3—H3B	107.9	C17—C12—C13	119.87 (12)
C5—C4—C3	109.89 (11)	C17—C12—N3	121.61 (11)
C5—C4—H4A	109.7	C13—C12—N3	118.44 (11)
C3—C4—H4A	109.7	C14—C13—C12	120.06 (12)
C5—C4—H4B	109.7	C14—C13—H13	120.0
C3—C4—H4B	109.7	C12—C13—H13	120.0
H4A—C4—H4B	108.2	C13—C14—C15	120.17 (13)
C6—C5—C4	110.78 (11)	C13—C14—H14	119.9
C6—C5—H5A	109.5	C15—C14—H14	119.9
C4—C5—H5A	109.5	C16—C15—C14	119.45 (13)
C6—C5—H5B	109.5	C16—C15—H15	120.3
C4—C5—H5B	109.5	C14—C15—H15	120.3
H5A—C5—H5B	108.1	C15—C16—C17	120.79 (12)
C7—C6—C11	118.80 (13)	C15—C16—H16	119.6
C7—C6—C5	120.80 (12)	C17—C16—H16	119.6
C11—C6—C5	120.40 (12)	C16—C17—C12	119.66 (12)
C8—C7—C6	121.45 (13)	C16—C17—H17	120.2
C8—C7—H7	119.3	C12—C17—H17	120.2
C6—C7—H7	119.3
N3—C1—N1—N2	−9.03 (16)	C5—C6—C11—C10	176.54 (12)
S1—C1—N1—N2	169.57 (9)	C7—C6—C11—C2	175.51 (11)
C1—N1—N2—C2	−172.78 (11)	C5—C6—C11—C2	−5.79 (18)
N1—N2—C2—C11	175.47 (10)	N2—C2—C11—C10	11.35 (18)
N1—N2—C2—C3	−1.69 (18)	C3—C2—C11—C10	−171.33 (12)
N2—C2—C3—C4	−163.68 (12)	N2—C2—C11—C6	−166.29 (11)
C11—C2—C3—C4	19.23 (16)	C3—C2—C11—C6	11.04 (17)
C2—C3—C4—C5	−53.39 (15)	N1—C1—N3—C12	−177.29 (12)
C3—C4—C5—C6	58.18 (15)	S1—C1—N3—C12	4.2 (2)
C4—C5—C6—C7	149.58 (12)	C1—N3—C12—C17	47.42 (19)
C4—C5—C6—C11	−29.09 (17)	C1—N3—C12—C13	−135.95 (14)
C11—C6—C7—C8	0.67 (19)	C17—C12—C13—C14	−0.13 (19)
C5—C6—C7—C8	−178.02 (13)	N3—C12—C13—C14	−176.81 (12)
C6—C7—C8—C9	1.4 (2)	C12—C13—C14—C15	−0.3 (2)
C7—C8—C9—C10	−1.9 (2)	C13—C14—C15—C16	0.3 (2)
C8—C9—C10—C11	0.4 (2)	C14—C15—C16—C17	0.1 (2)
C9—C10—C11—C6	1.6 (2)	C15—C16—C17—C12	−0.5 (2)
C9—C10—C11—C2	−175.99 (12)	C13—C12—C17—C16	0.51 (19)
C7—C6—C11—C10	−2.16 (18)	N3—C12—C17—C16	177.09 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1i	0.88	2.70	3.5793 (11)	176
N3—H2N···N2	0.88	2.12	2.5630 (15)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1i	0.88	2.70	3.5793 (11)	176
N3—H2N⋯N2	0.88	2.12	2.5630 (15)	111

Symmetry code: (i) .