1-Benzoyl-3,3-dibutyl-thio-urea.

The title mol-ecule, C(16)H(24)N(2)OS, is twisted about the central N(H)-C bond with a C-N(H)-C-N torsion angle of -62.67 (15)°. The carbonyl group is twisted out of the plane of the benzene ring, forming a C-C-C=O torsion angle of -25.06 (17)°. In the crystal, mol-ecules related by centres of symmetry are linked by pairs of inter-molecular N-H⋯S hydrogen bonds, forming eight-membered {⋯HNCS}(2) synthons. These are further connected by weak via C-H⋯O contacts, forming a two-dimensional array in the bc plane.

Related literature

For pharmaceutical applications of thio­urea derivatives, see: Binzet et al. (2009 ▶); Lipowska et al. (1996 ▶). For the coordination potential of thio­urea derivatives, see: Henderson et al. (2002 ▶); Hallale et al. (2005 ▶). For the use of ruthenium(III) complexes of thio­ureas as catalysts, see: Gunasekaran & Karvembu (2010 ▶). For related structures, see: Gunasekaran et al. (2010a ▶,b ▶).

Experimental

Crystal data

C16H24N2OS

M = 292.43

Monoclinic,

a = 10.3213 (7) Å

b = 15.7043 (11) Å

c = 10.0992 (7) Å

β = 98.751 (1)°

V = 1617.91 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.40 × 0.40 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.925, T max = 0.971

15120 measured reflections

3725 independent reflections

3204 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.03

3725 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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/S1600536810037177/lh5132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037177/lh5132Isup2.hkl

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

C16H24N2OS	F(000) = 632
Mr = 292.43	Dx = 1.201 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5696 reflections
a = 10.3213 (7) Å	θ = 4.4–28.3°
b = 15.7043 (11) Å	µ = 0.20 mm−1
c = 10.0992 (7) Å	T = 100 K
β = 98.751 (1)°	Block, colourless
V = 1617.91 (19) Å3	0.40 × 0.40 × 0.15 mm
Z = 4

Bruker SMART APEX diffractometer	3725 independent reflections
Radiation source: fine-focus sealed tube	3204 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.925, Tmax = 0.971	k = −20→20
15120 measured reflections	l = −13→12

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.602P] where P = (Fo2 + 2Fc2)/3
3725 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.31 e Å−3
1 restraint	Δρmin = −0.26 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	0.31557 (3)	0.56922 (2)	0.46025 (3)	0.01948 (10)
O1	0.49254 (9)	0.58166 (6)	0.12400 (9)	0.0197 (2)
N1	0.53208 (10)	0.59664 (7)	0.35231 (10)	0.0161 (2)
H1n	0.5663 (15)	0.5638 (9)	0.4155 (13)	0.027 (4)*
N2	0.36726 (10)	0.69784 (7)	0.30300 (10)	0.0178 (2)
C1	0.70516 (12)	0.54489 (8)	0.23442 (12)	0.0169 (2)
C2	0.73420 (13)	0.49345 (8)	0.13018 (13)	0.0214 (3)
H2A	0.6667	0.4767	0.0604	0.026*
C3	0.86217 (14)	0.46701 (9)	0.12914 (15)	0.0275 (3)
H3A	0.8821	0.4311	0.0592	0.033*
C4	0.96133 (14)	0.49266 (9)	0.22958 (15)	0.0281 (3)
H4A	1.0489	0.4746	0.2278	0.034*
C5	0.93326 (13)	0.54464 (9)	0.33254 (14)	0.0252 (3)
H5A	1.0014	0.5624	0.4010	0.030*
C6	0.80499 (13)	0.57064 (8)	0.33523 (13)	0.0205 (3)
H6A	0.7853	0.6060	0.4059	0.025*
C7	0.56729 (12)	0.57488 (7)	0.22861 (12)	0.0159 (2)
C8	0.40510 (12)	0.62549 (8)	0.36472 (12)	0.0164 (2)
C9	0.23215 (13)	0.72865 (8)	0.29594 (13)	0.0205 (3)
H9A	0.2320	0.7916	0.2996	0.025*
H9B	0.1944	0.7070	0.3739	0.025*
C10	0.14839 (12)	0.69899 (8)	0.16698 (13)	0.0202 (3)
H10A	0.1403	0.6362	0.1687	0.024*
H10B	0.1926	0.7144	0.0899	0.024*
C11	0.01211 (14)	0.73842 (9)	0.14782 (14)	0.0274 (3)
H11A	−0.0298	0.7261	0.2276	0.033*
H11B	0.0202	0.8010	0.1407	0.033*
C12	−0.07515 (14)	0.70524 (10)	0.02386 (14)	0.0282 (3)
H12A	−0.1617	0.7321	0.0166	0.042*
H12B	−0.0845	0.6434	0.0308	0.042*
H12C	−0.0356	0.7189	−0.0558	0.042*
C13	0.45409 (13)	0.75523 (8)	0.24042 (12)	0.0194 (3)
H13A	0.4005	0.7903	0.1711	0.023*
H13B	0.5153	0.7208	0.1959	0.023*
C14	0.53205 (13)	0.81332 (8)	0.34351 (13)	0.0218 (3)
H14A	0.5934	0.7786	0.4065	0.026*
H14B	0.4713	0.8425	0.3956	0.026*
C15	0.60954 (14)	0.87993 (8)	0.27769 (14)	0.0247 (3)
H15A	0.5473	0.9163	0.2184	0.030*
H15B	0.6574	0.9168	0.3483	0.030*
C16	0.70717 (14)	0.84140 (9)	0.19606 (14)	0.0265 (3)
H16A	0.7538	0.8871	0.1570	0.040*
H16B	0.6603	0.8061	0.1242	0.040*
H16C	0.7703	0.8062	0.2544	0.040*

	U11	U22	U33	U12	U13	U23
S1	0.01575 (16)	0.02258 (17)	0.02072 (17)	0.00138 (11)	0.00475 (12)	0.00432 (12)
O1	0.0204 (5)	0.0224 (4)	0.0150 (4)	−0.0002 (3)	−0.0014 (4)	−0.0001 (3)
N1	0.0144 (5)	0.0204 (5)	0.0133 (5)	0.0021 (4)	0.0010 (4)	0.0027 (4)
N2	0.0170 (5)	0.0197 (5)	0.0162 (5)	0.0014 (4)	0.0007 (4)	0.0015 (4)
C1	0.0165 (6)	0.0178 (6)	0.0169 (6)	−0.0016 (4)	0.0042 (5)	0.0036 (4)
C2	0.0238 (7)	0.0202 (6)	0.0207 (6)	−0.0016 (5)	0.0048 (5)	0.0000 (5)
C3	0.0292 (8)	0.0245 (7)	0.0310 (8)	0.0039 (6)	0.0121 (6)	−0.0009 (6)
C4	0.0199 (7)	0.0292 (7)	0.0372 (8)	0.0061 (5)	0.0102 (6)	0.0093 (6)
C5	0.0179 (7)	0.0312 (7)	0.0258 (7)	−0.0025 (5)	0.0010 (5)	0.0064 (6)
C6	0.0191 (6)	0.0247 (6)	0.0178 (6)	−0.0020 (5)	0.0038 (5)	0.0020 (5)
C7	0.0174 (6)	0.0143 (5)	0.0160 (6)	−0.0028 (4)	0.0026 (5)	0.0009 (4)
C8	0.0146 (6)	0.0199 (6)	0.0140 (6)	0.0005 (4)	−0.0001 (4)	−0.0013 (4)
C9	0.0199 (6)	0.0220 (6)	0.0191 (6)	0.0066 (5)	0.0015 (5)	0.0000 (5)
C10	0.0190 (6)	0.0241 (6)	0.0171 (6)	0.0036 (5)	0.0016 (5)	0.0003 (5)
C11	0.0239 (7)	0.0314 (7)	0.0248 (7)	0.0096 (6)	−0.0025 (5)	−0.0028 (6)
C12	0.0210 (7)	0.0386 (8)	0.0238 (7)	0.0056 (6)	−0.0008 (5)	0.0007 (6)
C13	0.0229 (6)	0.0174 (6)	0.0176 (6)	−0.0008 (5)	0.0019 (5)	0.0023 (5)
C14	0.0217 (7)	0.0247 (6)	0.0190 (6)	0.0007 (5)	0.0028 (5)	−0.0045 (5)
C15	0.0270 (7)	0.0216 (6)	0.0247 (7)	−0.0026 (5)	0.0013 (5)	−0.0051 (5)
C16	0.0227 (7)	0.0313 (7)	0.0253 (7)	−0.0010 (6)	0.0029 (6)	0.0025 (6)

S1—C8	1.6843 (13)	C9—H9B	0.9900
O1—C7	1.2144 (15)	C10—C11	1.5221 (18)
N1—C7	1.3955 (16)	C10—H10A	0.9900
N1—C8	1.4102 (16)	C10—H10B	0.9900
N1—H1n	0.854 (9)	C11—C12	1.5188 (19)
N2—C8	1.3259 (16)	C11—H11A	0.9900
N2—C9	1.4675 (16)	C11—H11B	0.9900
N2—C13	1.4790 (16)	C12—H12A	0.9800
C1—C6	1.3938 (18)	C12—H12B	0.9800
C1—C2	1.3953 (18)	C12—H12C	0.9800
C1—C7	1.4915 (17)	C13—C14	1.5194 (17)
C2—C3	1.3861 (19)	C13—H13A	0.9900
C2—H2A	0.9500	C13—H13B	0.9900
C3—C4	1.387 (2)	C14—C15	1.5289 (19)
C3—H3A	0.9500	C14—H14A	0.9900
C4—C5	1.387 (2)	C14—H14B	0.9900
C4—H4A	0.9500	C15—C16	1.5212 (19)
C5—C6	1.3896 (19)	C15—H15A	0.9900
C5—H5A	0.9500	C15—H15B	0.9900
C6—H6A	0.9500	C16—H16A	0.9800
C9—C10	1.5225 (18)	C16—H16B	0.9800
C9—H9A	0.9900	C16—H16C	0.9800
C7—N1—C8	122.03 (10)	C9—C10—H10B	109.2
C7—N1—H1n	112.7 (11)	C11—C10—H10B	109.2
C8—N1—H1n	114.3 (11)	H10A—C10—H10B	107.9
C8—N2—C9	121.01 (11)	C12—C11—C10	112.69 (12)
C8—N2—C13	124.66 (11)	C12—C11—H11A	109.1
C9—N2—C13	114.30 (10)	C10—C11—H11A	109.1
C6—C1—C2	119.95 (12)	C12—C11—H11B	109.1
C6—C1—C7	122.14 (11)	C10—C11—H11B	109.1
C2—C1—C7	117.80 (11)	H11A—C11—H11B	107.8
C3—C2—C1	119.57 (13)	C11—C12—H12A	109.5
C3—C2—H2A	120.2	C11—C12—H12B	109.5
C1—C2—H2A	120.2	H12A—C12—H12B	109.5
C4—C3—C2	120.37 (13)	C11—C12—H12C	109.5
C4—C3—H3A	119.8	H12A—C12—H12C	109.5
C2—C3—H3A	119.8	H12B—C12—H12C	109.5
C3—C4—C5	120.29 (13)	N2—C13—C14	111.42 (10)
C3—C4—H4A	119.9	N2—C13—H13A	109.3
C5—C4—H4A	119.9	C14—C13—H13A	109.3
C4—C5—C6	119.73 (13)	N2—C13—H13B	109.3
C4—C5—H5A	120.1	C14—C13—H13B	109.3
C6—C5—H5A	120.1	H13A—C13—H13B	108.0
C5—C6—C1	120.08 (13)	C13—C14—C15	111.74 (11)
C5—C6—H6A	120.0	C13—C14—H14A	109.3
C1—C6—H6A	120.0	C15—C14—H14A	109.3
O1—C7—N1	122.67 (11)	C13—C14—H14B	109.3
O1—C7—C1	122.54 (11)	C15—C14—H14B	109.3
N1—C7—C1	114.77 (10)	H14A—C14—H14B	107.9
N2—C8—N1	116.41 (11)	C16—C15—C14	113.39 (11)
N2—C8—S1	124.81 (10)	C16—C15—H15A	108.9
N1—C8—S1	118.73 (9)	C14—C15—H15A	108.9
N2—C9—C10	110.64 (10)	C16—C15—H15B	108.9
N2—C9—H9A	109.5	C14—C15—H15B	108.9
C10—C9—H9A	109.5	H15A—C15—H15B	107.7
N2—C9—H9B	109.5	C15—C16—H16A	109.5
C10—C9—H9B	109.5	C15—C16—H16B	109.5
H9A—C9—H9B	108.1	H16A—C16—H16B	109.5
C9—C10—C11	112.19 (11)	C15—C16—H16C	109.5
C9—C10—H10A	109.2	H16A—C16—H16C	109.5
C11—C10—H10A	109.2	H16B—C16—H16C	109.5
C6—C1—C2—C3	1.20 (19)	C9—N2—C8—N1	172.80 (10)
C7—C1—C2—C3	177.48 (11)	C13—N2—C8—N1	−9.26 (17)
C1—C2—C3—C4	−1.2 (2)	C9—N2—C8—S1	−9.85 (17)
C2—C3—C4—C5	0.4 (2)	C13—N2—C8—S1	168.09 (9)
C3—C4—C5—C6	0.4 (2)	C7—N1—C8—N2	−62.67 (15)
C4—C5—C6—C1	−0.3 (2)	C7—N1—C8—S1	119.81 (11)
C2—C1—C6—C5	−0.46 (19)	C8—N2—C9—C10	−93.34 (14)
C7—C1—C6—C5	−176.57 (12)	C13—N2—C9—C10	88.52 (13)
C8—N1—C7—O1	2.17 (18)	N2—C9—C10—C11	−173.07 (11)
C8—N1—C7—C1	−179.45 (11)	C9—C10—C11—C12	−176.53 (12)
C6—C1—C7—O1	151.14 (12)	C8—N2—C13—C14	−82.29 (15)
C2—C1—C7—O1	−25.06 (17)	C9—N2—C13—C14	95.77 (12)
C6—C1—C7—N1	−27.25 (16)	N2—C13—C14—C15	−173.16 (10)
C2—C1—C7—N1	156.56 (11)	C13—C14—C15—C16	−59.57 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S1i	0.85 (1)	2.64 (1)	3.4547 (11)	160 (1)
C2—H2a···O1ii	0.95	2.47	3.4102 (16)	173
C14—H14b···O1iii	0.99	2.58	3.3559 (16)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯S1i	0.85 (1)	2.64 (1)	3.4547 (11)	160 (1)
C2—H2a⋯O1ii	0.95	2.47	3.4102 (16)	173
C14—H14b⋯O1iii	0.99	2.58	3.3559 (16)	136

Symmetry codes: (i) ; (ii) ; (iii) .