(E)-1-(4-Methyl-phen-yl)-3-[(1-phenyl-ethyl-idene)amino]-thio-urea.

In the title compound, C(16)H(17)N(3)S, the amino-thio-urea unit is nearly planar (r.m.s. deviation = 0.0425 Å), and is twisted with respect to the tolyl and phenyl rings by 57.84 (7) and 15.88 (14)°, respectively; the tolyl and phenyl rings are twisted by 65.64 (11)° to each other. Inter-molecular N-H⋯S and weak C-H⋯S hydrogen bonds are present in the crystal structure.

Related literature

The title compound is a derivative of thio­semicarbazone. For applications of thio­semicarbazones in the biological field, see: Hu et al. (2006 ▶).

Experimental

Crystal data

C16H17N3S

M = 283.39

Monoclinic,

a = 10.5881 (3) Å

b = 5.7355 (2) Å

c = 26.9746 (7) Å

β = 108.670 (2)°

V = 1551.91 (8) Å3

Z = 4

Cu Kα radiation

μ = 1.79 mm−1

T = 291 K

0.25 × 0.18 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.60, T max = 0.73

15835 measured reflections

2945 independent reflections

2587 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.126

S = 1.06

2945 reflections

191 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019404/xu5214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019404/xu5214Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019404/xu5214Isup3.cml

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

C16H17N3S	F(000) = 600
Mr = 283.39	Dx = 1.213 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 10.5881 (3) Å	Cell parameters from 6724 reflections
b = 5.7355 (2) Å	θ = 3.5–70.9°
c = 26.9746 (7) Å	µ = 1.79 mm−1
β = 108.670 (2)°	T = 291 K
V = 1551.91 (8) Å3	Prismatic, colorless
Z = 4	0.25 × 0.18 × 0.18 mm

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2945 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2587 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 16.2312 pixels mm-1	θmax = 70.9°, θmin = 3.5°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→6
Tmin = 0.60, Tmax = 0.73	l = −28→31
15835 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0693P)2 + 0.2489P] where P = (Fo2 + 2Fc2)/3
2945 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.23 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	1.08154 (5)	0.02598 (9)	0.436028 (18)	0.05334 (18)
N1	0.82552 (14)	0.5213 (3)	0.42960 (6)	0.0465 (3)
N2	0.90859 (14)	0.3341 (3)	0.44695 (6)	0.0499 (4)
N3	0.99833 (16)	0.4238 (3)	0.38311 (6)	0.0510 (4)
C1	1.06088 (19)	0.2091 (4)	0.31610 (7)	0.0559 (5)
H1	1.0044	0.0876	0.3179	0.067*
C2	1.1318 (2)	0.1997 (4)	0.28098 (7)	0.0656 (6)
H2A	1.1229	0.0699	0.2595	0.079*
C3	1.2149 (2)	0.3777 (5)	0.27725 (7)	0.0651 (6)
C4	1.2278 (2)	0.5681 (4)	0.30964 (8)	0.0630 (5)
H4	1.2841	0.6896	0.3077	0.076*
C5	1.15789 (19)	0.5810 (4)	0.34519 (7)	0.0520 (4)
H5	1.1672	0.7109	0.3667	0.062*
C6	1.07490 (16)	0.4014 (3)	0.34853 (6)	0.0443 (4)
C7	1.2928 (3)	0.3658 (8)	0.23886 (12)	0.1137 (13)
H7A	1.2491	0.4593	0.2087	0.171*
H7B	1.2971	0.2070	0.2283	0.171*
H7C	1.3814	0.4237	0.2553	0.171*
C8	0.99248 (15)	0.2719 (3)	0.42007 (6)	0.0440 (4)
C9	0.74014 (16)	0.5714 (3)	0.45287 (7)	0.0437 (4)
C10	0.64955 (15)	0.7680 (3)	0.43048 (6)	0.0452 (4)
C11	0.6772 (2)	0.9235 (4)	0.39573 (7)	0.0584 (5)
H11	0.7547	0.9058	0.3869	0.070*
C12	0.5910 (3)	1.1032 (5)	0.37429 (9)	0.0761 (7)
H12	0.6102	1.2057	0.3510	0.091*
C13	0.4749 (2)	1.1320 (5)	0.38739 (9)	0.0783 (8)
H13	0.4162	1.2526	0.3726	0.094*
C14	0.4478 (2)	0.9828 (5)	0.42192 (12)	0.0773 (7)
H14	0.3707	1.0024	0.4309	0.093*
C15	0.53386 (19)	0.8031 (4)	0.44367 (10)	0.0665 (6)
H15	0.5146	0.7037	0.4675	0.080*
C16	0.7269 (2)	0.4397 (4)	0.49895 (8)	0.0570 (5)
H16A	0.6858	0.5377	0.5182	0.086*
H16B	0.8137	0.3932	0.5212	0.086*
H16C	0.6728	0.3038	0.4869	0.086*
H2	0.904 (2)	0.230 (4)	0.4714 (8)	0.058 (6)*
H3	0.960 (2)	0.548 (4)	0.3831 (8)	0.053 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0594 (3)	0.0488 (3)	0.0626 (3)	0.01893 (19)	0.0347 (2)	0.01199 (19)
N1	0.0428 (7)	0.0442 (9)	0.0593 (8)	0.0093 (6)	0.0257 (6)	0.0052 (6)
N2	0.0502 (8)	0.0488 (9)	0.0607 (8)	0.0150 (7)	0.0319 (6)	0.0117 (7)
N3	0.0550 (8)	0.0492 (10)	0.0578 (8)	0.0193 (7)	0.0305 (7)	0.0099 (7)
C1	0.0614 (10)	0.0575 (12)	0.0464 (8)	0.0029 (9)	0.0138 (7)	−0.0037 (8)
C2	0.0828 (13)	0.0722 (15)	0.0404 (8)	0.0195 (11)	0.0177 (8)	−0.0086 (8)
C3	0.0717 (12)	0.0870 (17)	0.0436 (9)	0.0292 (12)	0.0282 (8)	0.0116 (9)
C4	0.0648 (11)	0.0709 (14)	0.0624 (11)	0.0067 (10)	0.0333 (9)	0.0157 (10)
C5	0.0624 (10)	0.0480 (11)	0.0518 (9)	0.0075 (8)	0.0268 (8)	0.0018 (7)
C6	0.0450 (8)	0.0503 (10)	0.0395 (7)	0.0137 (7)	0.0162 (6)	0.0063 (6)
C7	0.130 (3)	0.159 (3)	0.0798 (16)	0.037 (2)	0.0733 (18)	0.0119 (19)
C8	0.0398 (7)	0.0478 (10)	0.0487 (8)	0.0052 (7)	0.0201 (6)	0.0017 (7)
C9	0.0392 (7)	0.0441 (10)	0.0535 (8)	0.0035 (7)	0.0229 (6)	0.0005 (7)
C10	0.0375 (7)	0.0506 (10)	0.0490 (8)	0.0058 (7)	0.0159 (6)	−0.0033 (7)
C11	0.0623 (11)	0.0632 (13)	0.0556 (10)	0.0202 (9)	0.0273 (8)	0.0082 (9)
C12	0.0911 (16)	0.0768 (17)	0.0577 (11)	0.0305 (13)	0.0201 (10)	0.0146 (11)
C13	0.0655 (12)	0.0806 (18)	0.0706 (13)	0.0360 (12)	−0.0040 (10)	−0.0071 (12)
C14	0.0433 (10)	0.0823 (18)	0.1062 (18)	0.0183 (10)	0.0237 (11)	−0.0094 (14)
C15	0.0480 (10)	0.0686 (15)	0.0930 (14)	0.0100 (9)	0.0367 (10)	0.0057 (12)
C16	0.0595 (10)	0.0586 (12)	0.0638 (10)	0.0104 (9)	0.0351 (8)	0.0095 (9)

S1—C8	1.6746 (18)	C7—H7A	0.9600
N1—N2	1.372 (2)	C7—H7B	0.9600
N1—C9	1.287 (2)	C7—H7C	0.9600
N2—C8	1.362 (2)	C9—C10	1.478 (2)
N2—H2	0.90 (2)	C9—C16	1.499 (2)
N3—C6	1.424 (2)	C10—C11	1.391 (3)
N3—C8	1.340 (2)	C10—C15	1.395 (2)
N3—H3	0.82 (2)	C11—H11	0.9300
C1—H1	0.9300	C11—C12	1.375 (3)
C1—C2	1.386 (3)	C12—H12	0.9300
C1—C6	1.386 (3)	C12—C13	1.393 (4)
C2—H2A	0.9300	C13—H13	0.9300
C2—C3	1.373 (4)	C13—C14	1.361 (4)
C3—C4	1.378 (4)	C14—H14	0.9300
C3—C7	1.517 (3)	C14—C15	1.376 (3)
C4—H4	0.9300	C15—H15	0.9300
C4—C5	1.388 (3)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C5—C6	1.376 (3)	C16—H16C	0.9600
C9—N1—N2	118.83 (15)	N2—C8—S1	119.57 (13)
N1—N2—H2	126.2 (14)	N3—C8—S1	125.62 (12)
C8—N2—N1	118.67 (15)	N3—C8—N2	114.78 (16)
C8—N2—H2	114.3 (14)	N1—C9—C10	115.87 (15)
C6—N3—H3	117.8 (16)	N1—C9—C16	123.94 (16)
C8—N3—C6	126.88 (15)	C10—C9—C16	120.17 (14)
C8—N3—H3	115.0 (16)	C11—C10—C9	121.03 (15)
C2—C1—H1	120.3	C11—C10—C15	118.04 (18)
C2—C1—C6	119.4 (2)	C15—C10—C9	120.93 (17)
C6—C1—H1	120.3	C10—C11—H11	119.7
C1—C2—H2A	119.3	C12—C11—C10	120.6 (2)
C3—C2—C1	121.4 (2)	C12—C11—H11	119.7
C3—C2—H2A	119.3	C11—C12—H12	119.9
C2—C3—C4	118.58 (18)	C11—C12—C13	120.2 (2)
C2—C3—C7	121.2 (3)	C13—C12—H12	119.9
C4—C3—C7	120.2 (3)	C12—C13—H13	120.2
C3—C4—H4	119.5	C14—C13—C12	119.7 (2)
C3—C4—C5	121.0 (2)	C14—C13—H13	120.2
C5—C4—H4	119.5	C13—C14—H14	119.8
C4—C5—H5	120.1	C13—C14—C15	120.5 (2)
C6—C5—C4	119.86 (19)	C15—C14—H14	119.8
C6—C5—H5	120.1	C10—C15—H15	119.5
C1—C6—N3	121.13 (18)	C14—C15—C10	121.0 (2)
C5—C6—N3	119.00 (17)	C14—C15—H15	119.5
C5—C6—C1	119.75 (16)	C9—C16—H16A	109.5
C3—C7—H7A	109.5	C9—C16—H16B	109.5
C3—C7—H7B	109.5	C9—C16—H16C	109.5
C3—C7—H7C	109.5	H16A—C16—H16B	109.5
H7A—C7—H7B	109.5	H16A—C16—H16C	109.5
H7A—C7—H7C	109.5	H16B—C16—H16C	109.5
H7B—C7—H7C	109.5
N1—N2—C8—S1	−172.72 (13)	C6—C1—C2—C3	−0.6 (3)
N1—N2—C8—N3	9.3 (2)	C7—C3—C4—C5	−179.6 (2)
N1—C9—C10—C11	−15.8 (3)	C8—N3—C6—C1	56.4 (3)
N1—C9—C10—C15	164.35 (19)	C8—N3—C6—C5	−127.6 (2)
N2—N1—C9—C10	−177.12 (15)	C9—N1—N2—C8	175.59 (16)
N2—N1—C9—C16	1.2 (3)	C9—C10—C11—C12	178.7 (2)
C1—C2—C3—C4	0.4 (3)	C9—C10—C15—C14	−178.5 (2)
C1—C2—C3—C7	179.7 (2)	C10—C11—C12—C13	0.3 (4)
C2—C1—C6—N3	176.51 (16)	C11—C10—C15—C14	1.6 (3)
C2—C1—C6—C5	0.6 (3)	C11—C12—C13—C14	0.6 (4)
C2—C3—C4—C5	−0.3 (3)	C12—C13—C14—C15	−0.4 (4)
C3—C4—C5—C6	0.3 (3)	C13—C14—C15—C10	−0.8 (4)
C4—C5—C6—N3	−176.47 (16)	C15—C10—C11—C12	−1.4 (3)
C4—C5—C6—C1	−0.4 (3)	C16—C9—C10—C11	165.88 (19)
C6—N3—C8—S1	3.6 (3)	C16—C9—C10—C15	−14.0 (3)
C6—N3—C8—N2	−178.56 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.90 (2)	2.86 (2)	3.7456 (16)	167.8 (19)
C16—H16B···S1i	0.96	2.74	3.471 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.90 (2)	2.86 (2)	3.7456 (16)	167.8 (19)
C16—H16B⋯S1i	0.96	2.74	3.471 (2)	133

Symmetry code: (i) .