1-(2-Amino-eth-yl)-3-phenyl-thio-urea.

In the crystal structure of the title compound, C(9)H(13)N(3)S, mol-ecules are linked through N-H⋯S and N-H⋯N hydrogen bonds, forming hydrogen-bonded tapes along the b axis. The dihedral angle between the phenyl ring and the thiourea group is 44.9 (2)°.

Related literature

For the synthesis of the title compund, see: Lee et al. (1985 ▶). For applications of thio­ureas, see: Tommasino et al. (1999 ▶, 2000 ▶); Leung et al. (2008 ▶). For similar structures, see: Guo (2007 ▶); Okino et al. (2005 ▶).

Experimental

Crystal data

C9H13N3S

M = 195.28

Monoclinic,

a = 8.5105 (2) Å

b = 11.5644 (3) Å

c = 9.9829 (3) Å

β = 93.580 (1)°

V = 980.59 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.52 × 0.51 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

11919 measured reflections

2365 independent reflections

1893 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.05

2365 reflections

134 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536811036476/fy2013sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036476/fy2013Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036476/fy2013Isup3.cml

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

C9H13N3S	F(000) = 416
Mr = 195.28	Dx = 1.323 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4309 reflections
a = 8.5105 (2) Å	θ = 2.4–28.3°
b = 11.5644 (3) Å	µ = 0.29 mm−1
c = 9.9829 (3) Å	T = 173 K
β = 93.580 (1)°	Plate, colourless
V = 980.59 (5) Å3	0.52 × 0.51 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	1893 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 28.0°, θmin = 2.4°
φ and ω scans	h = −11→11
11919 measured reflections	k = −15→15
2365 independent reflections	l = −13→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.1114P] where P = (Fo2 + 2Fc2)/3
2365 reflections	(Δ/σ)max = 0.001
134 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.31 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	0.70454 (14)	0.28612 (11)	−0.12947 (13)	0.0231 (3)
C2	0.67903 (16)	0.18764 (12)	−0.20730 (13)	0.0276 (3)
H2	0.5781	0.1523	−0.2139	0.033*
C3	0.80133 (18)	0.14084 (13)	−0.27550 (14)	0.0337 (3)
H3	0.7842	0.0726	−0.3273	0.040*
C4	0.94801 (17)	0.19291 (15)	−0.26863 (15)	0.0384 (4)
H4	1.0311	0.1611	−0.3162	0.046*
C5	0.97292 (15)	0.29189 (15)	−0.19184 (15)	0.0349 (4)
H5	1.0734	0.3280	−0.1872	0.042*
C6	0.85235 (14)	0.33857 (13)	−0.12171 (14)	0.0279 (3)
H6	0.8704	0.4060	−0.0686	0.033*
C7	0.46708 (13)	0.29317 (11)	0.00584 (13)	0.0232 (3)
C8	0.35806 (15)	0.12066 (11)	0.11161 (14)	0.0258 (3)
H8A	0.3210	0.1745	0.1800	0.031*
H8B	0.4109	0.0549	0.1593	0.031*
C9	0.21718 (15)	0.07587 (12)	0.02639 (14)	0.0283 (3)
H9A	0.1427	0.0379	0.0848	0.034*
H9B	0.1620	0.1415	−0.0196	0.034*
N1	0.58075 (12)	0.34090 (10)	−0.06492 (12)	0.0252 (3)
N2	0.47210 (12)	0.18047 (9)	0.03209 (11)	0.0235 (2)
S1	0.32346 (4)	0.38159 (3)	0.06009 (4)	0.02980 (13)
N3	0.26714 (14)	−0.00755 (11)	−0.07427 (13)	0.0323 (3)
H1N	0.5828 (17)	0.4185 (15)	−0.0621 (15)	0.031 (4)*
H2N	0.5532 (17)	0.1426 (13)	0.0186 (15)	0.027 (4)*
H3NA	0.298 (2)	0.0311 (17)	−0.147 (2)	0.056 (6)*
H3NB	0.186 (2)	−0.0499 (16)	−0.1047 (18)	0.049 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0229 (6)	0.0241 (7)	0.0226 (6)	0.0037 (5)	0.0050 (5)	0.0048 (5)
C2	0.0300 (7)	0.0281 (7)	0.0253 (7)	0.0017 (5)	0.0051 (5)	0.0027 (6)
C3	0.0454 (8)	0.0328 (8)	0.0237 (7)	0.0089 (6)	0.0090 (6)	0.0002 (6)
C4	0.0348 (8)	0.0516 (10)	0.0301 (8)	0.0151 (7)	0.0128 (6)	0.0063 (7)
C5	0.0222 (6)	0.0520 (10)	0.0310 (8)	0.0032 (6)	0.0065 (5)	0.0080 (7)
C6	0.0246 (6)	0.0333 (8)	0.0260 (7)	−0.0006 (5)	0.0036 (5)	0.0032 (6)
C7	0.0203 (6)	0.0219 (7)	0.0275 (7)	−0.0019 (5)	0.0028 (5)	−0.0025 (5)
C8	0.0274 (6)	0.0219 (7)	0.0287 (7)	−0.0015 (5)	0.0075 (5)	0.0018 (5)
C9	0.0235 (6)	0.0244 (7)	0.0373 (8)	0.0010 (5)	0.0047 (5)	0.0031 (6)
N1	0.0227 (5)	0.0176 (6)	0.0362 (7)	0.0001 (4)	0.0095 (5)	−0.0001 (5)
N2	0.0215 (5)	0.0192 (6)	0.0307 (6)	0.0012 (4)	0.0073 (4)	0.0000 (5)
S1	0.02171 (17)	0.0211 (2)	0.0478 (2)	0.00148 (12)	0.01190 (14)	−0.00020 (15)
N3	0.0303 (6)	0.0302 (7)	0.0362 (7)	−0.0015 (5)	−0.0006 (5)	−0.0048 (6)

C1—C2	1.3881 (19)	C7—N1	1.3509 (16)
C1—C6	1.3943 (17)	C7—S1	1.7074 (12)
C1—N1	1.4181 (15)	C8—N2	1.4651 (16)
C2—C3	1.3887 (19)	C8—C9	1.5173 (19)
C2—H2	0.9500	C8—H8A	0.9900
C3—C4	1.384 (2)	C8—H8B	0.9900
C3—H3	0.9500	C9—N3	1.4747 (18)
C4—C5	1.387 (2)	C9—H9A	0.9900
C4—H4	0.9500	C9—H9B	0.9900
C5—C6	1.3871 (18)	N1—H1N	0.898 (17)
C5—H5	0.9500	N2—H2N	0.836 (15)
C6—H6	0.9500	N3—H3NA	0.91 (2)
C7—N2	1.3296 (17)	N3—H3NB	0.882 (19)
C2—C1—C6	119.80 (12)	N2—C8—C9	112.61 (11)
C2—C1—N1	121.75 (11)	N2—C8—H8A	109.1
C6—C1—N1	118.27 (12)	C9—C8—H8A	109.1
C1—C2—C3	119.89 (13)	N2—C8—H8B	109.1
C1—C2—H2	120.1	C9—C8—H8B	109.1
C3—C2—H2	120.1	H8A—C8—H8B	107.8
C4—C3—C2	120.50 (14)	N3—C9—C8	110.73 (10)
C4—C3—H3	119.7	N3—C9—H9A	109.5
C2—C3—H3	119.7	C8—C9—H9A	109.5
C3—C4—C5	119.53 (13)	N3—C9—H9B	109.5
C3—C4—H4	120.2	C8—C9—H9B	109.5
C5—C4—H4	120.2	H9A—C9—H9B	108.1
C4—C5—C6	120.53 (13)	C7—N1—C1	129.17 (11)
C4—C5—H5	119.7	C7—N1—H1N	113.9 (9)
C6—C5—H5	119.7	C1—N1—H1N	116.5 (9)
C5—C6—C1	119.73 (14)	C7—N2—C8	123.73 (11)
C5—C6—H6	120.1	C7—N2—H2N	119.9 (10)
C1—C6—H6	120.1	C8—N2—H2N	115.0 (10)
N2—C7—N1	119.23 (11)	C9—N3—H3NA	109.6 (12)
N2—C7—S1	122.64 (9)	C9—N3—H3NB	110.3 (11)
N1—C7—S1	118.12 (10)	H3NA—N3—H3NB	104.6 (17)
C6—C1—C2—C3	0.9 (2)	N2—C8—C9—N3	60.48 (15)
N1—C1—C2—C3	176.02 (12)	N2—C7—N1—C1	6.3 (2)
C1—C2—C3—C4	−1.3 (2)	S1—C7—N1—C1	−174.59 (10)
C2—C3—C4—C5	0.7 (2)	C2—C1—N1—C7	44.9 (2)
C3—C4—C5—C6	0.3 (2)	C6—C1—N1—C7	−139.94 (14)
C4—C5—C6—C1	−0.6 (2)	N1—C7—N2—C8	177.90 (12)
C2—C1—C6—C5	0.0 (2)	S1—C7—N2—C8	−1.17 (18)
N1—C1—C6—C5	−175.28 (12)	C9—C8—N2—C7	89.72 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1i	0.898 (17)	2.445 (17)	3.3108 (12)	162.0 (12)
N2—H2N···N3ii	0.836 (15)	2.232 (15)	2.9974 (16)	152.5 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1i	0.898 (17)	2.445 (17)	3.3108 (12)	162.0 (12)
N2—H2N⋯N3ii	0.836 (15)	2.232 (15)	2.9974 (16)	152.5 (13)

Symmetry codes: (i) ; (ii) .