1-(2-Chloro-phen-yl)-3-(2-ethyl-hexa-noyl)thio-urea.

In the title compound, C15H21ClN2OS, the central chromophore moiety (C2N2OS) is approximately planar, with a maximum deviation of -0.027 (1) Å, and is oriented at a dihedral angle of 86.7 (1)° with respect to the chloro-phenyl ring. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation. In the crystal, mol-ecules associate via N-H⋯S hydrogen bonds, forming inversion dimers with motif R 2 (2)(8). These dimers are further connected by N-H⋯O hydrogen bonds, forming R 2 (2)(12) dimers. As a result, hydrogen-bonded chains running along [110] are formed. C-H⋯S inter-actions also occur. The terminal two C atoms of the butyl chain are disordered over two positions with an occupancy ratio of 0.54:0.46.

Related literature

For general background to the biological activity of thio­urea derivatives, see: Yang et al. (2012 ▶); Wu et al. (2012 ▶); Abbas et al. (2013 ▶); Ryu et al. (2012 ▶).

Experimental

Crystal data

C15H21ClN2OS

M = 312.85

Triclinic,

a = 7.264 (5) Å

b = 10.056 (7) Å

c = 11.935 (9) Å

α = 97.748 (17)°

β = 98.100 (17)°

γ = 103.72 (2)°

V = 825.5 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 292 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

8136 measured reflections

2878 independent reflections

1700 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.230

S = 1.02

2878 reflections

200 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301828X/bt6917sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301828X/bt6917Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301828X/bt6917Isup3.cml

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

C15H21ClN2OS	Z = 2
Mr = 312.85	F(000) = 332
Triclinic, P1	Dx = 1.259 Mg m−3
a = 7.264 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.056 (7) Å	Cell parameters from 6222 reflections
c = 11.935 (9) Å	θ = 2.3–24.8°
α = 97.748 (17)°	µ = 0.36 mm−1
β = 98.100 (17)°	T = 292 K
γ = 103.72 (2)°	Block, colourless
V = 825.5 (11) Å3	0.22 × 0.20 × 0.18 mm

Bruker SMART APEX CCD area-detector diffractometer	Rint = 0.067
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.8°
ω scans	h = −8→8
8136 measured reflections	k = −11→11
2878 independent reflections	l = −14→14
1700 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.076	H-atom parameters constrained
wR(F2) = 0.230	w = 1/[σ2(Fo2) + (0.125P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2878 reflections	Δρmax = 0.37 e Å−3
200 parameters	Δρmin = −0.26 e Å−3
4 restraints

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.0875 (2)	0.56892 (16)	−0.31845 (12)	0.0787 (5)
S1	0.23733 (18)	0.95432 (13)	−0.12264 (10)	0.0649 (5)
O1	0.1744 (4)	0.6032 (3)	0.0822 (3)	0.0589 (9)
N1	0.0376 (5)	0.7093 (4)	−0.0934 (3)	0.0478 (9)
H1	0.0249	0.6407	−0.0566	0.057*
N2	0.3169 (5)	0.8104 (4)	0.0374 (3)	0.0480 (9)
H2	0.4181	0.8790	0.0578	0.058*
C1	−0.2560 (7)	0.7626 (5)	−0.1733 (4)	0.0581 (12)
H1A	−0.2591	0.8089	−0.1010	0.070*
C2	−0.4017 (7)	0.7532 (6)	−0.2651 (5)	0.0677 (15)
H2A	−0.5034	0.7921	−0.2547	0.081*
C3	−0.3938 (8)	0.6860 (6)	−0.3712 (5)	0.0733 (16)
H3	−0.4911	0.6795	−0.4329	0.088*
C4	−0.2470 (8)	0.6287 (5)	−0.3879 (4)	0.0645 (14)
H4	−0.2441	0.5826	−0.4604	0.077*
C5	−0.1014 (6)	0.6392 (5)	−0.2968 (4)	0.0514 (12)
C6	−0.1079 (6)	0.7039 (4)	−0.1892 (3)	0.0425 (10)
C7	0.1916 (6)	0.8164 (4)	−0.0593 (3)	0.0455 (11)
C8	0.3017 (6)	0.7097 (5)	0.1054 (3)	0.0454 (10)
C9	0.4490 (7)	0.7445 (5)	0.2141 (4)	0.0563 (13)
H9	0.5358	0.8356	0.2147	0.068*
C10	0.5689 (8)	0.6399 (6)	0.2138 (4)	0.0719 (15)
H10A	0.6536	0.6587	0.2878	0.086*
H10B	0.4831	0.5478	0.2056	0.086*
C11	0.6883 (9)	0.6393 (7)	0.1219 (5)	0.094 (2)
H11A	0.6062	0.6196	0.0480	0.142*
H11B	0.7572	0.5693	0.1274	0.142*
H11C	0.7783	0.7287	0.1312	0.142*
C12	0.3511 (8)	0.7576 (6)	0.3165 (4)	0.0711 (15)
H12A	0.2709	0.6665	0.3194	0.085*
H12B	0.4495	0.7845	0.3853	0.085*
C13	0.2284 (12)	0.8584 (8)	0.3208 (5)	0.110 (2)
H13A	0.1449	0.8468	0.2473	0.132*	0.46
H13B	0.3081	0.9534	0.3400	0.132*	0.46
H13C	0.1402	0.8344	0.2478	0.132*	0.54
H13D	0.3138	0.9487	0.3212	0.132*	0.54
C14	0.104 (3)	0.8234 (19)	0.4181 (15)	0.109 (8)	0.46
H14A	−0.0231	0.8385	0.4033	0.131*	0.46
H14B	0.0991	0.7324	0.4382	0.131*	0.46
C15	0.251 (4)	0.941 (2)	0.499 (3)	0.187 (13)	0.46
H15A	0.2142	0.9492	0.5737	0.280*	0.46
H15B	0.2567	1.0259	0.4705	0.280*	0.46
H15C	0.3751	0.9218	0.5057	0.280*	0.46
C14'	0.105 (3)	0.882 (2)	0.4141 (13)	0.174 (14)	0.54
H14C	0.0756	0.9708	0.4128	0.209*	0.54
H14D	−0.0164	0.8103	0.3945	0.209*	0.54
C15'	0.197 (3)	0.879 (2)	0.5325 (13)	0.141 (10)	0.54
H15D	0.1141	0.8968	0.5853	0.211*	0.54
H15E	0.3176	0.9491	0.5529	0.211*	0.54
H15F	0.2200	0.7893	0.5360	0.211*	0.54

	U11	U22	U33	U12	U13	U23
Cl1	0.0737 (10)	0.0888 (11)	0.0753 (9)	0.0267 (8)	0.0178 (7)	0.0058 (8)
S1	0.0619 (8)	0.0570 (8)	0.0629 (8)	−0.0092 (6)	−0.0105 (6)	0.0332 (6)
O1	0.056 (2)	0.054 (2)	0.0582 (19)	−0.0049 (17)	−0.0026 (15)	0.0277 (16)
N1	0.048 (2)	0.047 (2)	0.0413 (19)	−0.0009 (18)	−0.0026 (16)	0.0199 (17)
N2	0.046 (2)	0.047 (2)	0.0398 (19)	−0.0049 (16)	−0.0046 (15)	0.0137 (16)
C1	0.055 (3)	0.061 (3)	0.057 (3)	0.010 (2)	0.007 (2)	0.015 (2)
C2	0.045 (3)	0.066 (3)	0.093 (4)	0.012 (3)	0.004 (3)	0.029 (3)
C3	0.065 (4)	0.081 (4)	0.067 (4)	0.010 (3)	−0.014 (3)	0.030 (3)
C4	0.073 (4)	0.066 (3)	0.044 (3)	0.003 (3)	−0.005 (2)	0.014 (2)
C5	0.043 (3)	0.057 (3)	0.051 (3)	0.003 (2)	0.004 (2)	0.022 (2)
C6	0.035 (2)	0.045 (2)	0.042 (2)	−0.0019 (19)	−0.0005 (18)	0.016 (2)
C7	0.044 (2)	0.050 (3)	0.035 (2)	0.000 (2)	0.0018 (18)	0.010 (2)
C8	0.044 (2)	0.051 (3)	0.042 (2)	0.007 (2)	0.0069 (19)	0.018 (2)
C9	0.057 (3)	0.062 (3)	0.046 (3)	0.003 (2)	−0.003 (2)	0.028 (2)
C10	0.068 (4)	0.083 (4)	0.063 (3)	0.023 (3)	−0.008 (3)	0.023 (3)
C11	0.086 (4)	0.123 (6)	0.089 (4)	0.045 (4)	0.018 (4)	0.033 (4)
C12	0.090 (4)	0.069 (3)	0.046 (3)	0.006 (3)	0.004 (3)	0.014 (3)
C13	0.161 (7)	0.129 (6)	0.063 (4)	0.081 (6)	0.025 (4)	0.017 (4)
C14	0.113 (14)	0.079 (15)	0.15 (2)	0.065 (12)	0.018 (12)	−0.013 (12)
C15	0.14 (2)	0.12 (2)	0.27 (4)	0.027 (16)	−0.07 (2)	0.04 (2)
C14'	0.27 (3)	0.13 (2)	0.144 (18)	0.16 (2)	−0.006 (17)	−0.049 (15)
C15'	0.27 (3)	0.143 (17)	0.089 (11)	0.130 (19)	0.113 (15)	0.073 (12)

Cl1—C5	1.720 (5)	C10—H10B	0.9700
S1—C7	1.655 (4)	C11—H11A	0.9600
O1—C8	1.206 (5)	C11—H11B	0.9600
N1—C7	1.326 (5)	C11—H11C	0.9600
N1—C6	1.430 (5)	C12—C13	1.501 (8)
N1—H1	0.8600	C12—H12A	0.9700
N2—C8	1.374 (5)	C12—H12B	0.9700
N2—C7	1.384 (5)	C13—C14'	1.553 (10)
N2—H2	0.8600	C13—C14	1.592 (10)
C1—C6	1.367 (6)	C13—H13A	0.9700
C1—C2	1.388 (7)	C13—H13B	0.9700
C1—H1A	0.9300	C13—H13C	0.9700
C2—C3	1.367 (7)	C13—H13D	0.9700
C2—H2A	0.9300	C14—C15	1.507 (10)
C3—C4	1.352 (7)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.379 (6)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.372 (6)	C15—H15C	0.9600
C8—C9	1.503 (6)	C14'—C15'	1.484 (10)
C9—C12	1.505 (7)	C14'—H14C	0.9700
C9—C10	1.516 (7)	C14'—H14D	0.9700
C9—H9	0.9800	C15'—H15D	0.9600
C10—C11	1.492 (8)	C15'—H15E	0.9600
C10—H10A	0.9700	C15'—H15F	0.9600
C7—N1—C6	122.2 (3)	C10—C11—H11C	109.5
C7—N1—H1	118.9	H11A—C11—H11C	109.5
C6—N1—H1	118.9	H11B—C11—H11C	109.5
C8—N2—C7	128.9 (4)	C13—C12—C9	116.9 (4)
C8—N2—H2	115.6	C13—C12—H12A	108.1
C7—N2—H2	115.6	C9—C12—H12A	108.1
C6—C1—C2	120.0 (5)	C13—C12—H12B	108.1
C6—C1—H1A	120.0	C9—C12—H12B	108.1
C2—C1—H1A	120.0	H12A—C12—H12B	107.3
C3—C2—C1	119.2 (5)	C12—C13—C14'	125.5 (8)
C3—C2—H2A	120.4	C12—C13—C14	105.6 (9)
C1—C2—H2A	120.4	C12—C13—H13A	110.6
C4—C3—C2	121.1 (5)	C14—C13—H13A	110.6
C4—C3—H3	119.4	C12—C13—H13B	110.6
C2—C3—H3	119.4	C14—C13—H13B	110.6
C3—C4—C5	119.6 (5)	H13A—C13—H13B	108.7
C3—C4—H4	120.2	C12—C13—H13C	105.9
C5—C4—H4	120.2	C14'—C13—H13C	105.9
C6—C5—C4	120.3 (5)	C12—C13—H13D	105.9
C6—C5—Cl1	120.0 (3)	C14'—C13—H13D	105.9
C4—C5—Cl1	119.7 (4)	H13C—C13—H13D	106.3
C1—C6—C5	119.7 (4)	C15—C14—C13	87.7 (19)
C1—C6—N1	119.8 (4)	C15—C14—H14A	114.0
C5—C6—N1	120.6 (4)	C13—C14—H14A	114.0
N1—C7—N2	116.1 (3)	C15—C14—H14B	114.0
N1—C7—S1	124.4 (3)	C13—C14—H14B	114.0
N2—C7—S1	119.5 (3)	H14A—C14—H14B	111.2
O1—C8—N2	122.6 (4)	C14—C15—H15A	109.5
O1—C8—C9	122.1 (4)	C14—C15—H15B	109.5
N2—C8—C9	115.3 (4)	H15A—C15—H15B	109.5
C8—C9—C12	109.7 (4)	C14—C15—H15C	109.5
C8—C9—C10	110.0 (4)	H15A—C15—H15C	109.5
C12—C9—C10	114.5 (4)	H15B—C15—H15C	109.5
C8—C9—H9	107.5	C15'—C14'—C13	114.4 (11)
C12—C9—H9	107.5	C15'—C14'—H14C	108.7
C10—C9—H9	107.5	C13—C14'—H14C	108.7
C11—C10—C9	115.2 (4)	C15'—C14'—H14D	108.7
C11—C10—H10A	108.5	C13—C14'—H14D	108.7
C9—C10—H10A	108.5	H14C—C14'—H14D	107.6
C11—C10—H10B	108.5	C14'—C15'—H15D	109.5
C9—C10—H10B	108.5	C14'—C15'—H15E	109.5
H10A—C10—H10B	107.5	H15D—C15'—H15E	109.5
C10—C11—H11A	109.5	C14'—C15'—H15F	109.5
C10—C11—H11B	109.5	H15D—C15'—H15F	109.5
H11A—C11—H11B	109.5	H15E—C15'—H15F	109.5
C6—C1—C2—C3	−0.7 (7)	C7—N2—C8—O1	5.4 (7)
C1—C2—C3—C4	0.0 (8)	C7—N2—C8—C9	−171.6 (4)
C2—C3—C4—C5	−0.6 (8)	O1—C8—C9—C12	−62.7 (6)
C3—C4—C5—C6	1.7 (7)	N2—C8—C9—C12	114.3 (4)
C3—C4—C5—Cl1	−178.9 (4)	O1—C8—C9—C10	64.0 (6)
C2—C1—C6—C5	1.8 (7)	N2—C8—C9—C10	−119.0 (4)
C2—C1—C6—N1	−177.5 (4)	C8—C9—C10—C11	64.0 (6)
C4—C5—C6—C1	−2.3 (7)	C12—C9—C10—C11	−172.0 (5)
Cl1—C5—C6—C1	178.3 (3)	C8—C9—C12—C13	−55.1 (6)
C4—C5—C6—N1	177.0 (4)	C10—C9—C12—C13	−179.3 (5)
Cl1—C5—C6—N1	−2.4 (6)	C9—C12—C13—C14'	176.0 (12)
C7—N1—C6—C1	−86.5 (5)	C9—C12—C13—C14	166.2 (9)
C7—N1—C6—C5	94.1 (5)	C12—C13—C14—C15	97.6 (12)
C6—N1—C7—N2	177.5 (4)	C14'—C13—C14—C15	−60 (3)
C6—N1—C7—S1	−1.0 (6)	C12—C13—C14'—C15'	39 (2)
C8—N2—C7—N1	−1.8 (7)	C14—C13—C14'—C15'	66 (4)
C8—N2—C7—S1	176.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.98	2.652 (4)	134
N1—H1···O1i	0.86	2.49	3.184 (5)	139
N2—H2···S1ii	0.86	2.61	3.451 (4)	168
C9—H9···S1ii	0.98	2.81	3.725 (5)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.98	2.652 (4)	134
N1—H1⋯O1i	0.86	2.49	3.184 (5)	139
N2—H2⋯S1ii	0.86	2.61	3.451 (4)	168
C9—H9⋯S1ii	0.98	2.81	3.725 (5)	157

Symmetry codes: (i) ; (ii) .