Crystal structure of 3-benzyl-1-[(1,2,3,4-tetra-hydro-naphthalen-1-yl-idene)amino]-thio-urea.

In the title compound, C18H19N3S, the dihedral angle between the planes of the benzene rings is 58.63 (8)°. The six-membered ring bonded to the thio-semicarbazide group (r.m.s. deviation = 0.038 Å) adopts a sofa conformation, with one of the methyl-ene-group C atoms as the flap. A short intra-molecular N-H⋯N contact is observed. In the crystal, mol-ecules are linked by weak N-H⋯S inter-actions to generate C(4) chains propagating in the [010] direction, with adjacent mol-ecules related by glide symmetry.

Related literature

For the anti­tumour activities of thio­semicarbazides, see: Vandresen et al. (2014 ▸); Xie et al. (2014 ▸); Gan et al. (2014 ▸). For the synthesis of the title compound, see: Mague et al. (2014 ▸)

Experimental

Crystal data

C18H19N3S

M = 309.42

Orthorhombic,

a = 11.9129 (5) Å

b = 9.6914 (4) Å

c = 27.8220 (11) Å

V = 3212.1 (2) Å3

Z = 8

Cu Kα radiation

μ = 1.77 mm−1

T = 150 K

0.22 × 0.18 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.84, T max = 0.91

61936 measured reflections

3155 independent reflections

2795 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.06

3155 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Bruker, 2014 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Bruker, 2014 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015021064/hb7536sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015021064/hb7536Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015021064/hb7536Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015021064/hb7536fig1.tif

The title mol­ecule with 50% probability displacement ellipsoids.

Click here for additional data file.

b . DOI: 10.1107/S2056989015021064/hb7536fig2.tif

Packing viewed down the b axis. N—H⋯S inter­actions are shown by dotted lines.

CCDC reference: 1435397

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

C18H19N3S	Dx = 1.280 Mg m−3
Mr = 309.42	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 9005 reflections
a = 11.9129 (5) Å	θ = 4.9–72.0°
b = 9.6914 (4) Å	µ = 1.77 mm−1
c = 27.8220 (11) Å	T = 150 K
V = 3212.1 (2) Å3	Tablet, colourless
Z = 8	0.22 × 0.18 × 0.05 mm
F(000) = 1312

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3155 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2795 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.050
Detector resolution: 10.4167 pixels mm-1	θmax = 72.2°, θmin = 3.2°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −11→11
Tmin = 0.84, Tmax = 0.91	l = −34→34
61936 measured reflections

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)] = 0.035	Hydrogen site location: mixed
wR(F2) = 0.098	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0522P)2 + 1.4441P] where P = (Fo2 + 2Fc2)/3
3155 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.22 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) while those attached to nitrogen were placed in locations derived from a difference map and their parameters adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
S1	0.08381 (3)	0.69807 (4)	0.37402 (2)	0.02936 (13)
N1	0.23130 (10)	0.48914 (12)	0.37501 (4)	0.0250 (3)
H1A	0.2789	0.4340	0.3581	0.030*
N2	0.18664 (10)	0.57805 (12)	0.30147 (4)	0.0243 (3)
H2A	0.1458	0.6361	0.2827	0.029*
N3	0.27037 (9)	0.49802 (12)	0.28232 (4)	0.0223 (3)
C1	0.29867 (14)	0.56296 (15)	0.45561 (5)	0.0287 (3)
C2	0.41047 (15)	0.57894 (19)	0.44281 (6)	0.0388 (4)
H2	0.4386	0.5343	0.4149	0.047*
C3	0.48124 (18)	0.6596 (2)	0.47050 (7)	0.0524 (5)
H3	0.5578	0.6695	0.4616	0.063*
C4	0.4413 (2)	0.7256 (2)	0.51086 (7)	0.0588 (6)
H4	0.4900	0.7817	0.5296	0.071*
C5	0.3306 (2)	0.7102 (2)	0.52401 (7)	0.0578 (6)
H5	0.3030	0.7551	0.5520	0.069*
C6	0.25919 (18)	0.62890 (19)	0.49641 (5)	0.0421 (4)
H6	0.1829	0.6185	0.5056	0.051*
C7	0.22186 (13)	0.47002 (15)	0.42688 (5)	0.0286 (3)
H7A	0.2394	0.3727	0.4347	0.034*
H7B	0.1433	0.4878	0.4367	0.034*
C8	0.17257 (12)	0.58125 (14)	0.35015 (5)	0.0231 (3)
C9	0.27768 (11)	0.49111 (13)	0.23608 (5)	0.0206 (3)
C10	0.19577 (13)	0.55643 (16)	0.20165 (5)	0.0298 (3)
H10A	0.2161	0.6546	0.1971	0.036*
H10B	0.1196	0.5531	0.2158	0.036*
C11	0.19402 (14)	0.48477 (18)	0.15289 (6)	0.0356 (4)
H11A	0.1620	0.3911	0.1564	0.043*
H11B	0.1459	0.5374	0.1304	0.043*
C12	0.31195 (14)	0.47477 (18)	0.13267 (5)	0.0339 (4)
H12A	0.3099	0.4231	0.1020	0.041*
H12B	0.3404	0.5687	0.1258	0.041*
C13	0.39089 (12)	0.40340 (15)	0.16706 (5)	0.0247 (3)
C14	0.48145 (13)	0.32664 (16)	0.14988 (6)	0.0305 (3)
H14	0.4926	0.3188	0.1162	0.037*
C15	0.55529 (13)	0.26181 (16)	0.18071 (6)	0.0328 (3)
H15	0.6154	0.2082	0.1683	0.039*
C16	0.54132 (12)	0.27535 (15)	0.22997 (6)	0.0299 (3)
H16	0.5928	0.2325	0.2514	0.036*
C17	0.45229 (12)	0.35136 (14)	0.24798 (5)	0.0242 (3)
H17	0.4436	0.3613	0.2817	0.029*
C18	0.37478 (11)	0.41390 (13)	0.21678 (5)	0.0206 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0343 (2)	0.0285 (2)	0.0252 (2)	0.00308 (14)	0.00802 (14)	−0.00293 (13)
N1	0.0291 (6)	0.0258 (6)	0.0200 (6)	−0.0001 (5)	0.0013 (5)	−0.0034 (5)
N2	0.0271 (6)	0.0254 (6)	0.0204 (6)	0.0045 (5)	0.0021 (5)	−0.0016 (5)
N3	0.0219 (6)	0.0218 (6)	0.0232 (6)	0.0000 (4)	0.0021 (4)	−0.0022 (4)
C1	0.0406 (8)	0.0263 (7)	0.0192 (6)	−0.0016 (6)	−0.0040 (6)	0.0049 (6)
C2	0.0412 (9)	0.0445 (9)	0.0308 (8)	−0.0055 (8)	−0.0046 (7)	0.0048 (7)
C3	0.0518 (11)	0.0630 (12)	0.0425 (10)	−0.0206 (10)	−0.0188 (9)	0.0151 (9)
C4	0.0905 (16)	0.0536 (12)	0.0325 (10)	−0.0305 (12)	−0.0287 (10)	0.0096 (8)
C5	0.0977 (18)	0.0514 (12)	0.0244 (8)	−0.0166 (12)	−0.0052 (10)	−0.0066 (8)
C6	0.0599 (11)	0.0423 (9)	0.0242 (7)	−0.0045 (8)	0.0025 (8)	−0.0027 (7)
C7	0.0368 (8)	0.0273 (7)	0.0217 (7)	−0.0036 (6)	0.0024 (6)	0.0023 (6)
C8	0.0248 (7)	0.0235 (7)	0.0209 (6)	−0.0058 (5)	0.0023 (5)	−0.0023 (5)
C9	0.0220 (7)	0.0183 (6)	0.0214 (6)	−0.0013 (5)	0.0002 (5)	−0.0013 (5)
C10	0.0322 (8)	0.0321 (8)	0.0250 (7)	0.0105 (6)	−0.0022 (6)	−0.0015 (6)
C11	0.0356 (8)	0.0438 (9)	0.0275 (8)	0.0066 (7)	−0.0063 (6)	−0.0026 (7)
C12	0.0364 (9)	0.0453 (9)	0.0202 (7)	0.0052 (7)	0.0011 (6)	−0.0011 (6)
C13	0.0248 (7)	0.0248 (7)	0.0244 (7)	−0.0029 (6)	0.0024 (5)	−0.0022 (5)
C14	0.0297 (8)	0.0322 (8)	0.0297 (7)	−0.0028 (6)	0.0098 (6)	−0.0042 (6)
C15	0.0243 (7)	0.0279 (7)	0.0463 (9)	0.0019 (6)	0.0096 (7)	−0.0046 (7)
C16	0.0232 (7)	0.0248 (7)	0.0417 (8)	0.0014 (6)	−0.0010 (6)	0.0028 (6)
C17	0.0234 (7)	0.0220 (7)	0.0270 (7)	−0.0026 (6)	−0.0002 (5)	0.0007 (6)
C18	0.0208 (6)	0.0171 (6)	0.0239 (7)	−0.0028 (5)	0.0017 (5)	−0.0007 (5)

S1—C8	1.6855 (14)	C9—C18	1.4786 (18)
N1—C8	1.3285 (19)	C9—C10	1.5069 (19)
N1—C7	1.4592 (17)	C10—C11	1.524 (2)
N1—H1A	0.9098	C10—H10A	0.9900
N2—C8	1.3651 (18)	C10—H10B	0.9900
N2—N3	1.3713 (16)	C11—C12	1.516 (2)
N2—H2A	0.9099	C11—H11A	0.9900
N3—C9	1.2913 (18)	C11—H11B	0.9900
C1—C6	1.385 (2)	C12—C13	1.509 (2)
C1—C2	1.387 (2)	C12—H12A	0.9900
C1—C7	1.512 (2)	C12—H12B	0.9900
C2—C3	1.384 (3)	C13—C14	1.395 (2)
C2—H2	0.9500	C13—C18	1.4004 (19)
C3—C4	1.377 (3)	C14—C15	1.380 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.377 (3)	C15—C16	1.387 (2)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.391 (3)	C16—C17	1.385 (2)
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.405 (2)
C7—H7A	0.9900	C17—H17	0.9500
C7—H7B	0.9900
C8—N1—C7	124.03 (12)	C9—C10—C11	112.53 (12)
C8—N1—H1A	116.9	C9—C10—H10A	109.1
C7—N1—H1A	119.0	C11—C10—H10A	109.1
C8—N2—N3	119.18 (12)	C9—C10—H10B	109.1
C8—N2—H2A	119.4	C11—C10—H10B	109.1
N3—N2—H2A	121.0	H10A—C10—H10B	107.8
C9—N3—N2	117.74 (12)	C12—C11—C10	110.29 (13)
C6—C1—C2	119.00 (16)	C12—C11—H11A	109.6
C6—C1—C7	120.17 (15)	C10—C11—H11A	109.6
C2—C1—C7	120.77 (14)	C12—C11—H11B	109.6
C3—C2—C1	120.34 (18)	C10—C11—H11B	109.6
C3—C2—H2	119.8	H11A—C11—H11B	108.1
C1—C2—H2	119.8	C13—C12—C11	111.79 (12)
C4—C3—C2	120.4 (2)	C13—C12—H12A	109.3
C4—C3—H3	119.8	C11—C12—H12A	109.3
C2—C3—H3	119.8	C13—C12—H12B	109.3
C5—C4—C3	119.80 (18)	C11—C12—H12B	109.3
C5—C4—H4	120.1	H12A—C12—H12B	107.9
C3—C4—H4	120.1	C14—C13—C18	118.90 (13)
C4—C5—C6	120.06 (19)	C14—C13—C12	120.60 (13)
C4—C5—H5	120.0	C18—C13—C12	120.50 (13)
C6—C5—H5	120.0	C15—C14—C13	121.51 (14)
C1—C6—C5	120.40 (19)	C15—C14—H14	119.2
C1—C6—H6	119.8	C13—C14—H14	119.2
C5—C6—H6	119.8	C14—C15—C16	119.66 (14)
N1—C7—C1	113.61 (12)	C14—C15—H15	120.2
N1—C7—H7A	108.8	C16—C15—H15	120.2
C1—C7—H7A	108.8	C17—C16—C15	119.98 (14)
N1—C7—H7B	108.8	C17—C16—H16	120.0
C1—C7—H7B	108.8	C15—C16—H16	120.0
H7A—C7—H7B	107.7	C16—C17—C18	120.62 (14)
N1—C8—N2	115.89 (12)	C16—C17—H17	119.7
N1—C8—S1	125.21 (10)	C18—C17—H17	119.7
N2—C8—S1	118.90 (11)	C13—C18—C17	119.28 (13)
N3—C9—C18	116.15 (12)	C13—C18—C9	120.18 (12)
N3—C9—C10	124.61 (12)	C17—C18—C9	120.54 (12)
C18—C9—C10	119.23 (12)
C8—N2—N3—C9	176.26 (12)	C9—C10—C11—C12	−52.80 (18)
C6—C1—C2—C3	0.0 (3)	C10—C11—C12—C13	55.55 (19)
C7—C1—C2—C3	−177.27 (16)	C11—C12—C13—C14	149.52 (14)
C1—C2—C3—C4	−0.4 (3)	C11—C12—C13—C18	−30.9 (2)
C2—C3—C4—C5	0.6 (3)	C18—C13—C14—C15	−0.3 (2)
C3—C4—C5—C6	−0.4 (3)	C12—C13—C14—C15	179.30 (15)
C2—C1—C6—C5	0.2 (3)	C13—C14—C15—C16	−1.5 (2)
C7—C1—C6—C5	177.49 (16)	C14—C15—C16—C17	1.3 (2)
C4—C5—C6—C1	0.0 (3)	C15—C16—C17—C18	0.8 (2)
C8—N1—C7—C1	−87.70 (17)	C14—C13—C18—C17	2.3 (2)
C6—C1—C7—N1	136.73 (15)	C12—C13—C18—C17	−177.28 (13)
C2—C1—C7—N1	−46.0 (2)	C14—C13—C18—C9	−178.21 (13)
C7—N1—C8—N2	−175.61 (13)	C12—C13—C18—C9	2.2 (2)
C7—N1—C8—S1	4.1 (2)	C16—C17—C18—C13	−2.6 (2)
N3—N2—C8—N1	−9.87 (18)	C16—C17—C18—C9	177.96 (13)
N3—N2—C8—S1	170.43 (10)	N3—C9—C18—C13	−178.67 (13)
N2—N3—C9—C18	174.84 (11)	C10—C9—C18—C13	0.82 (19)
N2—N3—C9—C10	−4.6 (2)	N3—C9—C18—C17	0.80 (19)
N3—C9—C10—C11	−155.52 (14)	C10—C9—C18—C17	−179.72 (13)
C18—C9—C10—C11	25.04 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.91	2.20	2.6219 (16)	108
N1—H1A···S1i	0.91	2.85	3.5790 (13)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3	0.91	2.20	2.6219 (16)	108
N1—H1A⋯S1i	0.91	2.85	3.5790 (13)	138

Symmetry code: (i) .