1-Benzoyl-3,3-bis-(2-methyl-prop-yl)thio-urea.

The title compound, C(16)H(24)N(2)OS, is twisted about the central N(H)-C bond with the C-N-C-S torsion angle being 119.6 (3)°. The carbonyl O and thione S atoms are directed to opposite sides of the mol-ecule, a conformation that allows for the formation of a linear supra-molecular chain comprising alternating eight-membered {⋯HNCS}(2) and 14-membered {⋯HCNCNCO}(2) synthons.

Related literature

For the coordinating ability of N,N-dialkyl-N′-benzoyl­thio­ureas; see: Binzet et al. (2009 ▶); Gunasekaran et al. (2010 ▶); Sacht et al. (2000 ▶). For the utility of Cd derivatives to serve as synthetic precursors for CdS nanoparticles, see: Bruce et al. (2007 ▶). For their biological activity, see: Arslan et al. (2006 ▶). For related structures, see: Gunasekaran et al. (2010a ▶,b ▶).

Experimental

Crystal data

C16H24N2OS

M = 292.43

Triclinic,

a = 8.9331 (10) Å

b = 10.1023 (9) Å

c = 11.0725 (12) Å

α = 105.776 (9)°

β = 112.734 (10)°

γ = 100.782 (9)°

V = 837.47 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 295 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent Supernova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.936, T max = 0.954

6265 measured reflections

3693 independent reflections

2232 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.219

S = 1.04

3693 reflections

181 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.58 e Å−3

Data collection: CrysAlis PRO (Agilent, 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004557/ez2230sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004557/ez2230Isup2.hkl

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

C16H24N2OS	Z = 2
Mr = 292.43	F(000) = 316
Triclinic, P1	Dx = 1.160 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9331 (10) Å	Cell parameters from 1845 reflections
b = 10.1023 (9) Å	θ = 2.2–29.2°
c = 11.0725 (12) Å	µ = 0.19 mm−1
α = 105.776 (9)°	T = 295 K
β = 112.734 (10)°	Block, colourless
γ = 100.782 (9)°	0.35 × 0.30 × 0.25 mm
V = 837.47 (19) Å3

Agilent Supernova Dual diffractometer with an Atlas detector	3693 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2232 reflections with I > 2σ(I)
Mirror	Rint = 0.025
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.2°
ω scans	h = −10→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→12
Tmin = 0.936, Tmax = 0.954	l = −14→12
6265 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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.078P)2 + 0.7593P] where P = (Fo2 + 2Fc2)/3
3693 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.86 e Å−3
12 restraints	Δρmin = −0.58 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 > 2σ(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	0.74828 (14)	0.92803 (11)	0.99096 (12)	0.0711 (4)
O1	0.6998 (3)	0.5295 (2)	0.7153 (3)	0.0585 (7)
N1	0.8690 (3)	0.7638 (3)	0.8494 (3)	0.0512 (7)
H1	0.9753	0.8236	0.8909	0.061*
N2	0.6172 (3)	0.7981 (3)	0.7098 (3)	0.0515 (7)
C1	0.9961 (4)	0.5699 (3)	0.8524 (3)	0.0431 (7)
C2	0.9697 (5)	0.4222 (4)	0.8112 (4)	0.0535 (9)
H2	0.8597	0.3566	0.7487	0.064*
C3	1.1045 (5)	0.3706 (4)	0.8615 (5)	0.0653 (11)
H3	1.0847	0.2708	0.8335	0.078*
C4	1.2664 (5)	0.4656 (5)	0.9522 (5)	0.0669 (11)
H4	1.3568	0.4306	0.9866	0.080*
C5	1.2961 (5)	0.6133 (5)	0.9929 (5)	0.0661 (11)
H5	1.4069	0.6780	1.0542	0.079*
C6	1.1618 (4)	0.6657 (4)	0.9431 (4)	0.0538 (9)
H6	1.1826	0.7656	0.9705	0.065*
C7	0.8421 (4)	0.6165 (3)	0.7986 (3)	0.0426 (7)
C8	0.7372 (4)	0.8250 (3)	0.8392 (4)	0.0513 (9)
C9	0.6351 (4)	0.7432 (3)	0.5811 (4)	0.0526 (9)
H9A	0.5352	0.6588	0.5122	0.063*
H9B	0.7353	0.7118	0.6035	0.063*
C10	0.6535 (5)	0.8564 (4)	0.5150 (4)	0.0654 (11)
H10	0.5463	0.8792	0.4831	0.079*
C11	0.6790 (7)	0.7906 (5)	0.3856 (4)	0.0892 (15)
H11A	0.5849	0.7025	0.3204	0.134*
H11B	0.7847	0.7691	0.4149	0.134*
H11C	0.6835	0.8587	0.3403	0.134*
C12	0.7998 (6)	0.9970 (4)	0.6237 (5)	0.0877 (15)
H12A	0.8091	1.0661	0.5801	0.132*
H12B	0.9057	0.9765	0.6583	0.132*
H12C	0.7765	1.0367	0.7012	0.132*
C13	0.4659 (4)	0.8426 (4)	0.6909 (5)	0.0662 (11)
H13A	0.4206	0.8536	0.6005	0.079*
H13B	0.5025	0.9377	0.7640	0.079*
C14	0.3240 (5)	0.7441 (4)	0.6949 (7)	0.106 (2)
H14	0.3640	0.7625	0.7957	0.127*
C15	0.1645 (5)	0.7914 (5)	0.6518 (6)	0.0888 (15)
H15A	0.1979	0.8950	0.6987	0.133*
H15B	0.0863	0.7435	0.6785	0.133*
H15C	0.1094	0.7655	0.5512	0.133*
C16	0.2816 (6)	0.5830 (4)	0.6261 (6)	0.0816 (13)
H16A	0.3853	0.5586	0.6554	0.122*
H16B	0.2264	0.5542	0.5251	0.122*
H16C	0.2058	0.5330	0.6536	0.122*

	U11	U22	U33	U12	U13	U23
S1	0.0676 (7)	0.0507 (6)	0.0765 (7)	0.0191 (5)	0.0294 (6)	0.0036 (5)
O1	0.0434 (13)	0.0383 (13)	0.0653 (16)	0.0071 (11)	0.0031 (12)	0.0157 (12)
N1	0.0344 (14)	0.0355 (15)	0.0622 (18)	0.0091 (12)	0.0100 (13)	0.0078 (13)
N2	0.0364 (14)	0.0400 (15)	0.0659 (19)	0.0137 (12)	0.0144 (14)	0.0156 (14)
C1	0.0428 (17)	0.0444 (18)	0.0423 (17)	0.0167 (15)	0.0181 (14)	0.0176 (14)
C2	0.054 (2)	0.0427 (19)	0.059 (2)	0.0190 (16)	0.0215 (17)	0.0169 (17)
C3	0.069 (3)	0.054 (2)	0.088 (3)	0.034 (2)	0.040 (2)	0.034 (2)
C4	0.055 (2)	0.077 (3)	0.089 (3)	0.039 (2)	0.035 (2)	0.046 (3)
C5	0.0419 (19)	0.071 (3)	0.077 (3)	0.0192 (19)	0.0186 (18)	0.029 (2)
C6	0.0451 (19)	0.050 (2)	0.060 (2)	0.0171 (16)	0.0180 (16)	0.0193 (17)
C7	0.0417 (17)	0.0384 (17)	0.0383 (16)	0.0125 (14)	0.0111 (14)	0.0128 (14)
C8	0.0403 (17)	0.0325 (17)	0.067 (2)	0.0098 (14)	0.0173 (16)	0.0118 (16)
C9	0.0438 (18)	0.0412 (19)	0.060 (2)	0.0136 (15)	0.0125 (16)	0.0183 (17)
C10	0.055 (2)	0.052 (2)	0.075 (3)	0.0160 (18)	0.0104 (19)	0.032 (2)
C11	0.113 (4)	0.077 (3)	0.071 (3)	0.025 (3)	0.033 (3)	0.038 (3)
C12	0.092 (3)	0.052 (3)	0.089 (3)	0.000 (2)	0.021 (3)	0.030 (2)
C13	0.046 (2)	0.057 (2)	0.089 (3)	0.0247 (18)	0.022 (2)	0.027 (2)
C14	0.065 (3)	0.072 (3)	0.203 (7)	0.033 (3)	0.070 (4)	0.065 (4)
C15	0.060 (3)	0.097 (4)	0.139 (5)	0.039 (3)	0.057 (3)	0.060 (4)
C16	0.071 (3)	0.057 (3)	0.113 (4)	0.012 (2)	0.047 (3)	0.027 (3)

S1—C8	1.673 (4)	C9—H9B	0.9700
O1—C7	1.214 (4)	C10—C12	1.528 (4)
N1—C7	1.377 (4)	C10—C11	1.529 (4)
N1—C8	1.410 (4)	C10—H10	0.9800
N1—H1	0.8800	C11—H11A	0.9600
N2—C8	1.330 (4)	C11—H11B	0.9600
N2—C13	1.461 (4)	C11—H11C	0.9600
N2—C9	1.464 (5)	C12—H12A	0.9600
C1—C2	1.380 (5)	C12—H12B	0.9600
C1—C6	1.386 (5)	C12—H12C	0.9600
C1—C7	1.493 (4)	C13—C14	1.482 (4)
C2—C3	1.381 (5)	C13—H13A	0.9700
C2—H2	0.9300	C13—H13B	0.9700
C3—C4	1.362 (6)	C14—C16	1.498 (4)
C3—H3	0.9300	C14—C15	1.530 (4)
C4—C5	1.376 (6)	C14—H14	0.9800
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.382 (5)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300	C16—H16A	0.9600
C9—C10	1.533 (4)	C16—H16B	0.9600
C9—H9A	0.9700	C16—H16C	0.9600
C7—N1—C8	124.2 (3)	C12—C10—H10	108.2
C7—N1—H1	117.9	C11—C10—H10	108.2
C8—N1—H1	117.9	C9—C10—H10	108.2
C8—N2—C13	120.0 (3)	C10—C11—H11A	109.5
C8—N2—C9	124.2 (3)	C10—C11—H11B	109.5
C13—N2—C9	115.2 (3)	H11A—C11—H11B	109.5
C2—C1—C6	118.6 (3)	C10—C11—H11C	109.5
C2—C1—C7	117.4 (3)	H11A—C11—H11C	109.5
C6—C1—C7	124.0 (3)	H11B—C11—H11C	109.5
C1—C2—C3	120.9 (4)	C10—C12—H12A	109.5
C1—C2—H2	119.6	C10—C12—H12B	109.5
C3—C2—H2	119.6	H12A—C12—H12B	109.5
C4—C3—C2	120.1 (4)	C10—C12—H12C	109.5
C4—C3—H3	119.9	H12A—C12—H12C	109.5
C2—C3—H3	119.9	H12B—C12—H12C	109.5
C3—C4—C5	120.0 (3)	N2—C13—C14	116.6 (3)
C3—C4—H4	120.0	N2—C13—H13A	108.1
C5—C4—H4	120.0	C14—C13—H13A	108.1
C4—C5—C6	120.2 (4)	N2—C13—H13B	108.1
C4—C5—H5	119.9	C14—C13—H13B	108.1
C6—C5—H5	119.9	H13A—C13—H13B	107.3
C5—C6—C1	120.2 (3)	C13—C14—C16	118.4 (4)
C5—C6—H6	119.9	C13—C14—C15	111.0 (3)
C1—C6—H6	119.9	C16—C14—C15	112.5 (4)
O1—C7—N1	121.4 (3)	C13—C14—H14	104.5
O1—C7—C1	122.1 (3)	C16—C14—H14	104.5
N1—C7—C1	116.6 (3)	C15—C14—H14	104.5
N2—C8—N1	117.1 (3)	C14—C15—H15A	109.5
N2—C8—S1	125.9 (3)	C14—C15—H15B	109.5
N1—C8—S1	117.1 (3)	H15A—C15—H15B	109.5
N2—C9—C10	113.3 (3)	C14—C15—H15C	109.5
N2—C9—H9A	108.9	H15A—C15—H15C	109.5
C10—C9—H9A	108.9	H15B—C15—H15C	109.5
N2—C9—H9B	108.9	C14—C16—H16A	109.5
C10—C9—H9B	108.9	C14—C16—H16B	109.5
H9A—C9—H9B	107.7	H16A—C16—H16B	109.5
C12—C10—C11	112.2 (3)	C14—C16—H16C	109.5
C12—C10—C9	110.9 (3)	H16A—C16—H16C	109.5
C11—C10—C9	109.1 (3)	H16B—C16—H16C	109.5
C6—C1—C2—C3	1.4 (5)	C13—N2—C8—N1	172.5 (3)
C7—C1—C2—C3	−177.1 (3)	C9—N2—C8—N1	−16.3 (5)
C1—C2—C3—C4	−0.5 (6)	C13—N2—C8—S1	−9.0 (5)
C2—C3—C4—C5	−0.5 (6)	C9—N2—C8—S1	162.2 (3)
C3—C4—C5—C6	0.6 (7)	C7—N1—C8—N2	−61.8 (5)
C4—C5—C6—C1	0.4 (6)	C7—N1—C8—S1	119.6 (3)
C2—C1—C6—C5	−1.4 (5)	C8—N2—C9—C10	−109.9 (4)
C7—C1—C6—C5	177.1 (3)	C13—N2—C9—C10	61.7 (4)
C8—N1—C7—O1	15.7 (5)	N2—C9—C10—C12	53.6 (4)
C8—N1—C7—C1	−163.6 (3)	N2—C9—C10—C11	177.6 (3)
C2—C1—C7—O1	−4.2 (5)	C8—N2—C13—C14	−82.1 (5)
C6—C1—C7—O1	177.4 (3)	C9—N2—C13—C14	105.9 (4)
C2—C1—C7—N1	175.2 (3)	N2—C13—C14—C16	−39.2 (7)
C6—C1—C7—N1	−3.3 (5)	N2—C13—C14—C15	−171.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.88	2.74	3.586 (3)	162
C9—H9a···O1ii	0.97	2.49	3.424 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.88	2.74	3.586 (3)	162
C9—H9a⋯O1ii	0.97	2.49	3.424 (5)	162

Symmetry codes: (i) ; (ii) .