3-Benzyl-5-butyl-1,3,5-thia-diazinane-2-thione.

In the title compound, C(14)H(20)N(2)S(2), the 1,3,5-thia-diazinane-2-thione ring adopts an envelope conformation. The S=C bond length is 1.6776 (15) Å, whereas the S-C bond lengths are 1.7470 (15) and 1.8479 (17) Å. The intramolecular C-H⋯S hydrogen bond between the thione and the benzyl units along with the C-H⋯π interaction between the butyl group and the centroid of the benzene ring may be effective in stabilizing the molecule.

Related literature

For the synthesis of the 1,3,5-thia­diazinane-2-thione nucleus, see: Aboul-fadi et al. (2002 ▶); Ertan et al. (1991 ▶, 1996 ▶). For its biological activity, see: Coro et al. (2005 ▶). For a related structure, see: Perez et al. (2001 ▶). For bond-length data, see: Allen (2002 ▶);

Experimental

Crystal data

C14H20N2S2

M = 280.44

Triclinic,

a = 7.6559 (2) Å

b = 9.9586 (3) Å

c = 11.1531 (4) Å

α = 66.917 (2)°

β = 70.649 (1)°

γ = 76.076 (2)°

V = 732.03 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 296 (2) K

0.26 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.922, T max = 0.942

15790 measured reflections

3759 independent reflections

2990 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.100

S = 1.03

3759 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003882/at2719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003882/at2719Isup2.hkl

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

C14H20N2S2	Z = 2
Mr = 280.44	F(000) = 300
Triclinic, P1	Dx = 1.272 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6559 (2) Å	Cell parameters from 2990 reflections
b = 9.9586 (3) Å	θ = 2.1–28.7°
c = 11.1531 (4) Å	µ = 0.35 mm−1
α = 66.917 (2)°	T = 296 K
β = 70.649 (1)°	Prismatic, colourless
γ = 76.076 (2)°	0.26 × 0.20 × 0.18 mm
V = 732.03 (4) Å3

Bruker Kappa APEXII CCD diffractometer	3759 independent reflections
Radiation source: fine-focus sealed tube	2990 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 7.40 pixels mm-1	θmax = 28.7°, θmin = 2.1°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→13
Tmin = 0.922, Tmax = 0.942	l = −15→14
15790 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1133P] where P = (Fo2 + 2Fc2)/3
3759 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.37143 (5)	0.10537 (5)	0.24801 (4)	0.0559 (1)
S2	0.72763 (5)	0.05293 (4)	0.29926 (4)	0.0542 (1)
N1	0.44875 (14)	0.24375 (12)	0.38422 (10)	0.0392 (3)
N2	0.76229 (15)	0.27317 (13)	0.37678 (11)	0.0446 (3)
C1	0.25768 (16)	0.48352 (15)	0.31596 (13)	0.0404 (4)
C2	0.20907 (19)	0.59310 (17)	0.37238 (15)	0.0501 (5)
C3	0.2155 (3)	0.73893 (19)	0.2912 (2)	0.0663 (6)
C4	0.2704 (3)	0.7760 (2)	0.1528 (2)	0.0733 (7)
C5	0.3168 (3)	0.6681 (2)	0.09567 (17)	0.0680 (6)
C6	0.3104 (2)	0.52245 (18)	0.17638 (15)	0.0525 (5)
C7	0.25828 (17)	0.32402 (15)	0.40427 (14)	0.0447 (4)
C8	0.50163 (17)	0.14720 (14)	0.32035 (13)	0.0408 (3)
C9	0.8377 (2)	0.12518 (17)	0.38223 (16)	0.0541 (5)
C10	0.56811 (17)	0.27834 (16)	0.44744 (13)	0.0431 (4)
C11	0.80744 (19)	0.38248 (16)	0.24024 (13)	0.0449 (4)
C12	0.7732 (2)	0.53983 (16)	0.23571 (14)	0.0488 (4)
C13	0.8309 (2)	0.64508 (17)	0.09273 (15)	0.0560 (5)
C14	0.8034 (3)	0.8041 (2)	0.0821 (2)	0.0821 (7)
H2	0.17173	0.56829	0.46589	0.0601*
H3	0.18275	0.81193	0.32993	0.0796*
H4	0.27603	0.87410	0.09782	0.0878*
H5	0.35270	0.69350	0.00210	0.0817*
H6	0.34143	0.45000	0.13712	0.0630*
H7A	0.20828	0.31702	0.49831	0.0537*
H7B	0.17844	0.27896	0.38314	0.0537*
H9A	0.82125	0.06214	0.47607	0.0649*
H9B	0.97069	0.12161	0.33891	0.0649*
H10A	0.52272	0.37597	0.45308	0.0516*
H10B	0.55480	0.20912	0.53898	0.0516*
H11A	0.73375	0.37322	0.18858	0.0538*
H11B	0.93788	0.36004	0.19640	0.0538*
H12A	0.84292	0.54959	0.28969	0.0586*
H12B	0.64162	0.56520	0.27472	0.0586*
H13A	0.96161	0.61717	0.05363	0.0672*
H13B	0.75950	0.63540	0.03977	0.0672*
H14A	0.84286	0.86437	−0.01109	0.1232*
H14B	0.87606	0.81541	0.13228	0.1232*
H14C	0.67380	0.83370	0.11828	0.1232*

	U11	U22	U33	U12	U13	U23
S1	0.0586 (2)	0.0591 (2)	0.0578 (2)	−0.0195 (2)	−0.0143 (2)	−0.0221 (2)
S2	0.0483 (2)	0.0444 (2)	0.0635 (3)	0.0008 (1)	−0.0102 (2)	−0.0197 (2)
N1	0.0350 (5)	0.0416 (6)	0.0381 (6)	−0.0065 (4)	−0.0072 (4)	−0.0118 (5)
N2	0.0389 (5)	0.0526 (7)	0.0390 (6)	−0.0087 (5)	−0.0112 (4)	−0.0100 (5)
C1	0.0315 (5)	0.0469 (7)	0.0422 (7)	−0.0041 (5)	−0.0099 (5)	−0.0150 (6)
C2	0.0469 (7)	0.0558 (9)	0.0505 (8)	−0.0020 (6)	−0.0139 (6)	−0.0230 (7)
C3	0.0691 (10)	0.0496 (9)	0.0874 (13)	0.0017 (7)	−0.0303 (9)	−0.0284 (9)
C4	0.0758 (11)	0.0464 (9)	0.0843 (14)	−0.0061 (8)	−0.0335 (10)	0.0005 (9)
C5	0.0694 (10)	0.0707 (11)	0.0470 (9)	−0.0072 (8)	−0.0176 (8)	−0.0018 (8)
C6	0.0538 (8)	0.0582 (9)	0.0446 (8)	−0.0032 (6)	−0.0131 (6)	−0.0189 (7)
C7	0.0341 (6)	0.0493 (8)	0.0443 (7)	−0.0075 (5)	−0.0021 (5)	−0.0148 (6)
C8	0.0415 (6)	0.0372 (6)	0.0365 (6)	−0.0109 (5)	−0.0062 (5)	−0.0052 (5)
C9	0.0422 (7)	0.0555 (9)	0.0545 (8)	−0.0025 (6)	−0.0164 (6)	−0.0076 (7)
C10	0.0434 (6)	0.0513 (8)	0.0331 (6)	−0.0106 (5)	−0.0087 (5)	−0.0115 (6)
C11	0.0448 (6)	0.0506 (8)	0.0380 (7)	−0.0121 (5)	−0.0067 (5)	−0.0139 (6)
C12	0.0507 (7)	0.0533 (8)	0.0435 (8)	−0.0120 (6)	−0.0096 (6)	−0.0169 (6)
C13	0.0636 (9)	0.0532 (9)	0.0485 (8)	−0.0137 (7)	−0.0140 (7)	−0.0116 (7)
C14	0.0893 (13)	0.0532 (10)	0.0946 (15)	−0.0123 (9)	−0.0219 (11)	−0.0158 (10)

S1—C8	1.6776 (15)	C3—H3	0.9300
S2—C8	1.7470 (15)	C4—H4	0.9300
S2—C9	1.8479 (17)	C5—H5	0.9300
N1—C7	1.4760 (19)	C6—H6	0.9300
N1—C8	1.3246 (18)	C7—H7A	0.9700
N1—C10	1.4899 (18)	C7—H7B	0.9700
N2—C9	1.433 (2)	C9—H9A	0.9700
N2—C10	1.4326 (19)	C9—H9B	0.9700
N2—C11	1.4683 (18)	C10—H10A	0.9700
C1—C2	1.383 (2)	C10—H10B	0.9700
C1—C6	1.387 (2)	C11—H11A	0.9700
C1—C7	1.505 (2)	C11—H11B	0.9700
C2—C3	1.380 (3)	C12—H12A	0.9700
C3—C4	1.376 (3)	C12—H12B	0.9700
C4—C5	1.375 (3)	C13—H13A	0.9700
C5—C6	1.378 (3)	C13—H13B	0.9700
C11—C12	1.509 (2)	C14—H14A	0.9600
C12—C13	1.511 (2)	C14—H14B	0.9600
C13—C14	1.508 (3)	C14—H14C	0.9600
C2—H2	0.9300
S1···H6	3.1400	H9A···S1iii	2.9300
S1···H7B	2.6000	H9B···S1vi	2.8800
S1···H9Bi	2.8800	H9B···H11B	2.2900
S1···H5ii	3.1600	H10A···C1	2.7100
S1···H9Aiii	2.9300	H10A···C2	2.9400
S1···H10Biii	3.1600	H10A···C12	2.7500
S2···H11A	2.9400	H10A···H7A	2.4600
N1···H11A	2.6800	H10A···H12B	2.2400
C6···C8	3.593 (2)	H10B···H9A	2.2800
C8···C11	3.374 (2)	H10B···S1iii	3.1600
C8···C6	3.593 (2)	H11A···S2	2.9400
C11···C8	3.374 (2)	H11A···N1	2.6800
C1···H12B	3.0800	H11A···C8	2.8300
C1···H10A	2.7100	H11A···H13B	2.5000
C2···H10A	2.9400	H11B···H9B	2.2900
C4···H14Bi	3.0200	H11B···H13A	2.4400
C5···H13Ai	3.0900	H11B···H13Avii	2.5700
C8···H11A	2.8300	H12A···H14B	2.5600
C10···H12B	2.8200	H12A···H2v	2.4800
C12···H10A	2.7500	H12B···C1	3.0800
C14···H4iv	3.0800	H12B···C10	2.8200
H2···H7A	2.3400	H12B···H10A	2.2400
H2···H12Av	2.4800	H12B···H14C	2.5700
H4···C14iv	3.0800	H13A···C5vi	3.0900
H4···H14Aiv	2.4500	H13A···H11B	2.4400
H5···S1ii	3.1600	H13A···H11Bvii	2.5700
H6···S1	3.1400	H13B···H11A	2.5000
H7A···H2	2.3400	H14A···H4iv	2.4500
H7A···H10A	2.4600	H14B···C4vi	3.0200
H7B···S1	2.6000	H14B···H12A	2.5600
H9A···H10B	2.2800	H14C···H12B	2.5700
C8—S2—C9	103.11 (7)	N1—C7—H7B	109.00
C7—N1—C8	122.01 (12)	C1—C7—H7A	109.00
C7—N1—C10	113.20 (11)	C1—C7—H7B	109.00
C8—N1—C10	124.74 (12)	H7A—C7—H7B	108.00
C9—N2—C10	109.50 (12)	S2—C9—H9A	109.00
C9—N2—C11	113.75 (12)	S2—C9—H9B	109.00
C10—N2—C11	115.24 (12)	N2—C9—H9A	109.00
C2—C1—C6	119.00 (14)	N2—C9—H9B	109.00
C2—C1—C7	120.70 (12)	H9A—C9—H9B	108.00
C6—C1—C7	120.29 (14)	N1—C10—H10A	109.00
C1—C2—C3	120.62 (15)	N1—C10—H10B	109.00
C2—C3—C4	119.82 (18)	N2—C10—H10A	109.00
C3—C4—C5	120.03 (18)	N2—C10—H10B	109.00
C4—C5—C6	120.31 (16)	H10A—C10—H10B	108.00
C1—C6—C5	120.21 (16)	N2—C11—H11A	109.00
N1—C7—C1	111.22 (11)	N2—C11—H11B	109.00
S1—C8—S2	112.92 (8)	C12—C11—H11A	109.00
S1—C8—N1	126.10 (11)	C12—C11—H11B	109.00
S2—C8—N1	120.94 (11)	H11A—C11—H11B	108.00
S2—C9—N2	113.13 (11)	C11—C12—H12A	109.00
N1—C10—N2	114.50 (11)	C11—C12—H12B	109.00
N2—C11—C12	114.63 (12)	C13—C12—H12A	109.00
C11—C12—C13	111.58 (12)	C13—C12—H12B	109.00
C12—C13—C14	113.99 (14)	H12A—C12—H12B	108.00
C1—C2—H2	120.00	C12—C13—H13A	109.00
C3—C2—H2	120.00	C12—C13—H13B	109.00
C2—C3—H3	120.00	C14—C13—H13A	109.00
C4—C3—H3	120.00	C14—C13—H13B	109.00
C3—C4—H4	120.00	H13A—C13—H13B	108.00
C5—C4—H4	120.00	C13—C14—H14A	109.00
C4—C5—H5	120.00	C13—C14—H14B	109.00
C6—C5—H5	120.00	C13—C14—H14C	109.00
C1—C6—H6	120.00	H14A—C14—H14B	109.00
C5—C6—H6	120.00	H14A—C14—H14C	109.00
N1—C7—H7A	109.00	H14B—C14—H14C	109.00
C9—S2—C8—S1	178.01 (8)	C9—N2—C11—C12	−165.23 (13)
C9—S2—C8—N1	−0.05 (12)	C10—N2—C11—C12	67.14 (17)
C8—S2—C9—N2	−29.53 (12)	C6—C1—C2—C3	−1.0 (2)
C8—N1—C7—C1	−108.21 (14)	C7—C1—C2—C3	177.50 (17)
C10—N1—C7—C1	74.18 (14)	C2—C1—C6—C5	1.0 (2)
C7—N1—C8—S1	2.68 (19)	C7—C1—C6—C5	−177.45 (17)
C7—N1—C8—S2	−179.54 (10)	C2—C1—C7—N1	−114.76 (15)
C10—N1—C8—S1	−180.00 (10)	C6—C1—C7—N1	63.68 (17)
C10—N1—C8—S2	−2.21 (18)	C1—C2—C3—C4	0.1 (3)
C7—N1—C10—N2	−147.79 (12)	C2—C3—C4—C5	0.7 (4)
C8—N1—C10—N2	34.68 (18)	C3—C4—C5—C6	−0.6 (4)
C10—N2—C9—S2	62.06 (13)	C4—C5—C6—C1	−0.2 (3)
C11—N2—C9—S2	−68.49 (15)	N2—C11—C12—C13	177.42 (13)
C9—N2—C10—N1	−65.65 (15)	C11—C12—C13—C14	−178.86 (16)
C11—N2—C10—N1	64.09 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···S1	0.97	2.60	3.0978 (16)	112
C12—H12B···CgA	0.97	2.96	3.7937 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯S1	0.97	2.60	3.0978 (16)	112
C12—H12B⋯CgA	0.97	2.96	3.7937 (19)	145

CgA is the centroid of the C1–C6 ring.