1-Benzyl-idene-amino-3-(4-methyl-phen-yl)thio-urea.

In the title compound, C(15)H(15)N(3)S, the almost planar 2-benzyl-idenehydrazinecarbothio-amide unit (r.m.s. deviation = 0.0351 Å) is aligned at a dihedral angle of 64.42 (6)° with respect to the plane of the tolyl ring. The mol-ecule exhibits an E configuration for the azomethine linkage. In the crystal, inter-molecular N-H⋯S hydrogen bonds about centers of inversion lead to the formation of dimers.

Related literature

For biological applications of thio­semicarbazones, see: Hu et al. (2006 ▶).

Experimental

Crystal data

C15H15N3S

M = 269.36

Monoclinic,

a = 10.2359 (3) Å

b = 16.0648 (3) Å

c = 9.9703 (3) Å

β = 117.154 (4)°

V = 1458.81 (7) Å3

Z = 4

Cu Kα radiation

μ = 1.88 mm−1

T = 293 K

0.30 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.603, T max = 0.729

12637 measured reflections

2605 independent reflections

2253 reflections with I > 2σ(I)

R int = 0.026

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.05

2605 reflections

181 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100198X/ng5104sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100198X/ng5104Isup2.hkl

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

C15H15N3S	F(000) = 568
Mr = 269.36	Dx = 1.226 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 7009 reflections
a = 10.2359 (3) Å	θ = 4.9–72.1°
b = 16.0648 (3) Å	µ = 1.88 mm−1
c = 9.9703 (3) Å	T = 293 K
β = 117.154 (4)°	Prismatic, colorless
V = 1458.81 (7) Å3	0.30 × 0.20 × 0.18 mm
Z = 4

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2605 independent reflections
Radiation source: fine-focus sealed tube	2253 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 67.1°, θmin = 4.9°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −12→12
Tmin = 0.603, Tmax = 0.729	k = −19→19
12637 measured reflections	l = −8→11

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.1569P] where P = (Fo2 + 2Fc2)/3
2605 reflections	(Δ/σ)max < 0.001
181 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
S1	0.13263 (6)	0.10810 (3)	0.02008 (5)	0.0727 (2)
N1	0.15900 (15)	−0.00305 (8)	0.37897 (15)	0.0546 (3)
N2	0.12114 (16)	0.01805 (8)	0.23296 (16)	0.0566 (3)
N3	0.28187 (16)	0.12678 (9)	0.31818 (17)	0.0599 (4)
C1	0.2093 (2)	−0.05346 (12)	0.6752 (2)	0.0684 (5)
H1	0.2567	−0.0052	0.6694	0.082*
C2	0.2298 (3)	−0.08202 (15)	0.8131 (2)	0.0815 (6)
H2A	0.2905	−0.0528	0.9000	0.098*
C3	0.1610 (3)	−0.15388 (14)	0.8239 (2)	0.0798 (6)
H3A	0.1763	−0.1736	0.9177	0.096*
C4	0.0699 (3)	−0.19596 (13)	0.6949 (2)	0.0765 (5)
H4	0.0226	−0.2441	0.7014	0.092*
C5	0.0481 (2)	−0.16751 (11)	0.5560 (2)	0.0667 (4)
H5	−0.0140	−0.1964	0.4693	0.080*
C6	0.11855 (18)	−0.09582 (10)	0.5445 (2)	0.0560 (4)
C7	0.09253 (18)	−0.06621 (10)	0.39603 (19)	0.0569 (4)
H7	0.0252	−0.0943	0.3110	0.068*
C8	0.18293 (17)	0.08400 (9)	0.20078 (19)	0.0532 (4)
C9	0.35959 (17)	0.19777 (10)	0.30466 (18)	0.0542 (4)
C10	0.4599 (2)	0.18975 (13)	0.2504 (3)	0.0838 (6)
H10	0.4801	0.1375	0.2241	0.101*
C11	0.5311 (3)	0.25904 (16)	0.2346 (3)	0.0938 (8)
H11	0.5983	0.2529	0.1965	0.113*
C12	0.5053 (2)	0.33670 (13)	0.2737 (2)	0.0750 (5)
C13	0.4092 (2)	0.34307 (11)	0.3338 (3)	0.0790 (5)
H13	0.3933	0.3948	0.3656	0.095*
C14	0.3353 (2)	0.27444 (11)	0.3483 (2)	0.0670 (5)
H14	0.2692	0.2804	0.3877	0.080*
C15	0.5825 (3)	0.41238 (18)	0.2529 (3)	0.1188 (11)
H15B	0.6778	0.3966	0.2653	0.178*
H15C	0.5928	0.4538	0.3265	0.178*
H15A	0.5257	0.4347	0.1536	0.178*
H2	0.054 (2)	−0.0105 (12)	0.158 (2)	0.067 (5)*
H3	0.294 (2)	0.1122 (12)	0.410 (3)	0.069 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0880 (4)	0.0664 (3)	0.0596 (3)	−0.0262 (2)	0.0302 (2)	0.00300 (19)
N1	0.0597 (7)	0.0492 (7)	0.0585 (8)	0.0007 (5)	0.0303 (6)	0.0018 (5)
N2	0.0642 (8)	0.0480 (7)	0.0573 (8)	−0.0075 (6)	0.0275 (7)	0.0007 (6)
N3	0.0670 (8)	0.0561 (7)	0.0596 (8)	−0.0104 (6)	0.0315 (7)	−0.0027 (6)
C1	0.0754 (11)	0.0668 (10)	0.0659 (11)	−0.0117 (8)	0.0349 (9)	−0.0038 (8)
C2	0.0902 (14)	0.0930 (14)	0.0586 (11)	−0.0119 (11)	0.0317 (10)	−0.0073 (10)
C3	0.0928 (14)	0.0919 (14)	0.0675 (12)	0.0027 (11)	0.0476 (11)	0.0111 (10)
C4	0.0926 (14)	0.0691 (11)	0.0825 (13)	−0.0089 (10)	0.0527 (12)	0.0085 (9)
C5	0.0784 (11)	0.0588 (9)	0.0701 (11)	−0.0105 (8)	0.0401 (9)	−0.0037 (8)
C6	0.0627 (9)	0.0510 (8)	0.0620 (9)	0.0003 (6)	0.0352 (8)	−0.0008 (7)
C7	0.0656 (9)	0.0496 (8)	0.0593 (9)	−0.0042 (7)	0.0317 (7)	−0.0034 (7)
C8	0.0561 (8)	0.0444 (7)	0.0634 (9)	0.0003 (6)	0.0309 (7)	0.0010 (6)
C9	0.0535 (8)	0.0537 (8)	0.0560 (8)	−0.0063 (6)	0.0257 (7)	−0.0044 (6)
C10	0.0799 (13)	0.0721 (12)	0.1209 (18)	−0.0164 (10)	0.0643 (13)	−0.0325 (12)
C11	0.0858 (14)	0.1098 (17)	0.1139 (18)	−0.0380 (13)	0.0699 (14)	−0.0354 (14)
C12	0.0735 (11)	0.0781 (12)	0.0649 (11)	−0.0267 (9)	0.0242 (9)	−0.0005 (9)
C13	0.0830 (13)	0.0539 (10)	0.0972 (15)	−0.0054 (9)	0.0387 (11)	−0.0048 (9)
C14	0.0668 (10)	0.0599 (10)	0.0840 (12)	−0.0036 (8)	0.0427 (9)	−0.0096 (8)
C15	0.123 (2)	0.117 (2)	0.1007 (19)	−0.0629 (18)	0.0376 (16)	0.0096 (15)

S1—C8	1.6776 (17)	C5—H5	0.9300
N1—C7	1.276 (2)	C6—C7	1.459 (2)
N1—N2	1.367 (2)	C7—H7	0.9300
N2—C8	1.346 (2)	C9—C14	1.366 (2)
N2—H2	0.88 (2)	C9—C10	1.368 (3)
N3—C8	1.336 (2)	C10—C11	1.378 (3)
N3—C9	1.432 (2)	C10—H10	0.9300
N3—H3	0.90 (2)	C11—C12	1.368 (3)
C1—C2	1.371 (3)	C11—H11	0.9300
C1—C6	1.386 (3)	C12—C13	1.370 (3)
C1—H1	0.9300	C12—C15	1.515 (3)
C2—C3	1.382 (3)	C13—C14	1.381 (3)
C2—H2A	0.9300	C13—H13	0.9300
C3—C4	1.374 (3)	C14—H14	0.9300
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.376 (3)	C15—H15C	0.9600
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.391 (2)
C7—N1—N2	115.46 (14)	N3—C8—N2	116.54 (15)
C8—N2—N1	120.89 (14)	N3—C8—S1	124.09 (12)
C8—N2—H2	118.7 (13)	N2—C8—S1	119.37 (13)
N1—N2—H2	120.4 (13)	C14—C9—C10	119.28 (16)
C8—N3—C9	123.97 (14)	C14—C9—N3	119.92 (15)
C8—N3—H3	117.3 (13)	C10—C9—N3	120.80 (15)
C9—N3—H3	118.6 (13)	C9—C10—C11	120.03 (18)
C2—C1—C6	120.59 (18)	C9—C10—H10	120.0
C2—C1—H1	119.7	C11—C10—H10	120.0
C6—C1—H1	119.7	C12—C11—C10	121.56 (19)
C1—C2—C3	120.49 (19)	C12—C11—H11	119.2
C1—C2—H2A	119.8	C10—C11—H11	119.2
C3—C2—H2A	119.8	C11—C12—C13	117.60 (18)
C4—C3—C2	119.36 (18)	C11—C12—C15	120.8 (2)
C4—C3—H3A	120.3	C13—C12—C15	121.6 (2)
C2—C3—H3A	120.3	C12—C13—C14	121.51 (19)
C3—C4—C5	120.53 (18)	C12—C13—H13	119.2
C3—C4—H4	119.7	C14—C13—H13	119.2
C5—C4—H4	119.7	C9—C14—C13	119.93 (17)
C4—C5—C6	120.38 (18)	C9—C14—H14	120.0
C4—C5—H5	119.8	C13—C14—H14	120.0
C6—C5—H5	119.8	C12—C15—H15B	109.5
C1—C6—C5	118.64 (16)	C12—C15—H15C	109.5
C1—C6—C7	121.86 (15)	H15B—C15—H15C	109.5
C5—C6—C7	119.48 (15)	C12—C15—H15A	109.5
N1—C7—C6	122.22 (15)	H15B—C15—H15A	109.5
N1—C7—H7	118.9	H15C—C15—H15A	109.5
C6—C7—H7	118.9
C7—N1—N2—C8	179.41 (15)	N1—N2—C8—N3	0.1 (2)
C6—C1—C2—C3	0.4 (3)	N1—N2—C8—S1	−179.63 (11)
C1—C2—C3—C4	−0.9 (4)	C8—N3—C9—C14	113.67 (19)
C2—C3—C4—C5	0.6 (3)	C8—N3—C9—C10	−67.3 (2)
C3—C4—C5—C6	0.2 (3)	C14—C9—C10—C11	−2.5 (3)
C2—C1—C6—C5	0.4 (3)	N3—C9—C10—C11	178.4 (2)
C2—C1—C6—C7	178.92 (18)	C9—C10—C11—C12	0.7 (4)
C4—C5—C6—C1	−0.7 (3)	C10—C11—C12—C13	2.0 (4)
C4—C5—C6—C7	−179.28 (17)	C10—C11—C12—C15	−178.9 (2)
N2—N1—C7—C6	−178.88 (14)	C11—C12—C13—C14	−3.0 (3)
C1—C6—C7—N1	4.7 (3)	C15—C12—C13—C14	177.9 (2)
C5—C6—C7—N1	−176.80 (16)	C10—C9—C14—C13	1.6 (3)
C9—N3—C8—N2	179.12 (14)	N3—C9—C14—C13	−179.34 (18)
C9—N3—C8—S1	−1.2 (2)	C12—C13—C14—C9	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.88 (2)	2.48 (2)	3.3522 (15)	170.3 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.88 (2)	2.48 (2)	3.3522 (15)	170.3 (17)

Symmetry code: (i) .