2-Methyl-3-(n-octylsulfan-yl)quinoxaline.

All the non-H atoms of the title compound, C(17)H(24)N(2)S, lie almost in a common plane (r.m.s. deviation = 0.049 Å). The octyl chain adopts an all-trans conformation.

Related literature

For the biological activity of quinoxaline derivatives, see: Kleim et al. (1995 ▶). For the anti­tumor and anti­tuberculous properties of quinoxaline derivatives, see: Abasolo et al. (1987 ▶); Rodrigo et al. (2002 ▶). For the anti­fungal, herbicidal, anti­dyslipidemic and anti-oxidative activity of quinoxaline derivatives, see: Jampilek et al. (2005 ▶); Sashidhara et al. (2009 ▶); Watkins et al. (2009 ▶).

Experimental

Crystal data

C17H24N2S

M = 288.44

Triclinic,

a = 7.3514 (3) Å

b = 8.2978 (3) Å

c = 14.2168 (5) Å

α = 92.275 (2)°

β = 98.706 (2)°

γ = 103.810 (2)°

V = 829.86 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.26 × 0.17 × 0.16 mm

Data collection

Bruker APEXII CCD detector diffractometer

29319 measured reflections

6513 independent reflections

3251 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.161

S = 1.00

6513 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011542/bt5230sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011542/bt5230Isup2.hkl

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

C17H24N2S	Z = 2
Mr = 288.44	F(000) = 312
Triclinic, P1	Dx = 1.154 Mg m−3
Hall symbol: -P 1	Melting point: 374 K
a = 7.3514 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2978 (3) Å	Cell parameters from 2685 reflections
c = 14.2168 (5) Å	θ = 2.5–27.3°
α = 92.275 (2)°	µ = 0.19 mm−1
β = 98.706 (2)°	T = 296 K
γ = 103.810 (2)°	Block, colourless
V = 829.86 (5) Å3	0.26 × 0.17 × 0.16 mm

Bruker APEXII CCD detector diffractometer	3251 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
graphite	θmax = 33.6°, θmin = 2.8°
ω and φ scans	h = −10→11
29319 measured reflections	k = −12→12
6513 independent reflections	l = −22→22

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0769P)2 + 0.0189P] where P = (Fo2 + 2Fc2)/3
6513 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. The data collection nominally covered a sphere of reciprocal space, by a combination of seven sets of exposures; each set had a different φ angle for the crystal and each exposure covered 0.5° in ω and 25 seconds in time. The crystal-to-detector distance was 37.5 mm.

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.

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	0.61857 (5)	0.28251 (5)	0.04284 (3)	0.05291 (14)
N2	0.67349 (16)	0.13786 (14)	−0.11823 (8)	0.0467 (3)
C8	0.54850 (18)	0.17628 (16)	−0.07085 (10)	0.0426 (3)
N1	0.28116 (16)	0.05407 (15)	−0.19181 (9)	0.0518 (3)
C10	0.87038 (19)	0.29990 (18)	0.06244 (11)	0.0493 (3)
H10A	0.8933	0.1896	0.0597	0.059*
H10B	0.9263	0.3596	0.0124	0.059*
C7	0.34717 (18)	0.13428 (17)	−0.10860 (11)	0.0472 (3)
C1	0.6056 (2)	0.05508 (17)	−0.20663 (10)	0.0476 (3)
C11	0.9631 (2)	0.39073 (19)	0.15840 (11)	0.0552 (4)
H11A	0.9086	0.3298	0.2085	0.066*
H11B	0.9379	0.5002	0.1615	0.066*
C6	0.4093 (2)	0.01226 (17)	−0.24318 (10)	0.0503 (3)
C12	1.1760 (2)	0.40888 (19)	0.17481 (11)	0.0550 (4)
H12A	1.1990	0.2989	0.1689	0.066*
H12B	1.2287	0.4711	0.1247	0.066*
C14	1.4944 (2)	0.5180 (2)	0.27832 (11)	0.0593 (4)
H14A	1.5201	0.4097	0.2689	0.071*
H14B	1.5369	0.5831	0.2270	0.071*
C13	1.2816 (2)	0.4944 (2)	0.27024 (11)	0.0571 (4)
H13A	1.2372	0.4285	0.3209	0.069*
H13B	1.2539	0.6022	0.2786	0.069*
C5	0.3444 (3)	−0.0724 (2)	−0.33399 (12)	0.0654 (4)
H5	0.2151	−0.1026	−0.3580	0.078*
C15	1.6108 (2)	0.6024 (2)	0.37177 (12)	0.0659 (4)
H15A	1.5757	0.5341	0.4231	0.079*
H15B	1.5811	0.7085	0.3835	0.079*
C9	0.2124 (2)	0.1842 (2)	−0.05151 (13)	0.0626 (4)
H9A	0.0860	0.1513	−0.0872	0.094*
H9B	0.2480	0.3028	−0.0377	0.094*
H9C	0.2166	0.1308	0.0072	0.094*
C2	0.7318 (3)	0.0135 (2)	−0.26280 (12)	0.0630 (4)
H2	0.8616	0.0409	−0.2397	0.076*
C16	1.8230 (3)	0.6316 (3)	0.37289 (14)	0.0818 (6)
H16A	1.8523	0.5247	0.3632	0.098*
H16B	1.8562	0.6956	0.3196	0.098*
C3	0.6642 (3)	−0.0667 (2)	−0.35107 (13)	0.0737 (5)
H3	0.7489	−0.0927	−0.3880	0.088*
C4	0.4702 (3)	−0.1106 (2)	−0.38715 (13)	0.0748 (5)
H4	0.4266	−0.1660	−0.4475	0.090*
C17	1.9438 (3)	0.7205 (3)	0.46263 (17)	0.1066 (8)
H17A	1.9224	0.8295	0.4708	0.160*
H17B	2.0752	0.7303	0.4587	0.160*
H17C	1.9114	0.6589	0.5160	0.160*

	U11	U22	U33	U12	U13	U23
S1	0.0394 (2)	0.0656 (2)	0.0517 (2)	0.01121 (16)	0.00697 (15)	−0.00649 (16)
N2	0.0370 (6)	0.0531 (6)	0.0480 (7)	0.0077 (5)	0.0075 (5)	0.0010 (5)
C8	0.0345 (7)	0.0467 (7)	0.0450 (7)	0.0078 (5)	0.0052 (5)	0.0039 (6)
N1	0.0393 (6)	0.0597 (7)	0.0529 (7)	0.0106 (5)	−0.0004 (5)	0.0030 (6)
C10	0.0370 (7)	0.0551 (8)	0.0511 (8)	0.0046 (6)	0.0052 (6)	−0.0026 (6)
C7	0.0346 (7)	0.0498 (7)	0.0555 (9)	0.0087 (6)	0.0049 (6)	0.0064 (6)
C1	0.0454 (8)	0.0501 (7)	0.0467 (8)	0.0093 (6)	0.0090 (6)	0.0041 (6)
C11	0.0465 (8)	0.0620 (9)	0.0523 (9)	0.0077 (7)	0.0041 (7)	−0.0011 (7)
C6	0.0489 (8)	0.0518 (8)	0.0468 (8)	0.0095 (6)	0.0018 (6)	0.0059 (6)
C12	0.0475 (8)	0.0601 (8)	0.0507 (8)	0.0058 (7)	0.0004 (7)	0.0006 (7)
C14	0.0528 (9)	0.0644 (9)	0.0518 (9)	0.0041 (7)	−0.0018 (7)	0.0044 (7)
C13	0.0518 (9)	0.0618 (9)	0.0514 (9)	0.0071 (7)	0.0009 (7)	0.0010 (7)
C5	0.0667 (11)	0.0707 (10)	0.0515 (9)	0.0130 (8)	−0.0048 (8)	−0.0018 (8)
C15	0.0579 (10)	0.0745 (10)	0.0554 (9)	0.0070 (8)	−0.0045 (8)	−0.0010 (8)
C9	0.0383 (8)	0.0779 (10)	0.0721 (11)	0.0181 (7)	0.0082 (7)	−0.0061 (8)
C2	0.0597 (10)	0.0699 (10)	0.0616 (10)	0.0151 (8)	0.0203 (8)	−0.0006 (8)
C16	0.0637 (12)	0.1066 (15)	0.0644 (11)	0.0139 (10)	−0.0064 (9)	−0.0109 (10)
C3	0.0848 (14)	0.0779 (11)	0.0645 (11)	0.0220 (10)	0.0298 (10)	−0.0013 (9)
C4	0.0960 (15)	0.0749 (11)	0.0481 (10)	0.0159 (10)	0.0067 (10)	−0.0051 (8)
C17	0.0735 (14)	0.138 (2)	0.0857 (16)	0.0068 (13)	−0.0159 (12)	−0.0248 (14)

S1—C8	1.7530 (14)	C14—H14B	0.9700
S1—C10	1.7995 (14)	C13—H13A	0.9700
N2—C8	1.3077 (18)	C13—H13B	0.9700
N2—C1	1.3705 (18)	C5—C4	1.363 (3)
C8—C7	1.4485 (18)	C5—H5	0.9300
N1—C7	1.2990 (18)	C15—C16	1.518 (2)
N1—C6	1.373 (2)	C15—H15A	0.9700
C10—C11	1.5119 (19)	C15—H15B	0.9700
C10—H10A	0.9700	C9—H9A	0.9600
C10—H10B	0.9700	C9—H9B	0.9600
C7—C9	1.491 (2)	C9—H9C	0.9600
C1—C2	1.405 (2)	C2—C3	1.361 (2)
C1—C6	1.411 (2)	C2—H2	0.9300
C11—C12	1.517 (2)	C16—C17	1.493 (2)
C11—H11A	0.9700	C16—H16A	0.9700
C11—H11B	0.9700	C16—H16B	0.9700
C6—C5	1.403 (2)	C3—C4	1.395 (3)
C12—C13	1.513 (2)	C3—H3	0.9300
C12—H12A	0.9700	C4—H4	0.9300
C12—H12B	0.9700	C17—H17A	0.9600
C14—C15	1.511 (2)	C17—H17B	0.9600
C14—C13	1.515 (2)	C17—H17C	0.9600
C14—H14A	0.9700
C8—S1—C10	101.52 (7)	C14—C13—H13A	109.2
C8—N2—C1	116.84 (12)	C12—C13—H13B	109.2
N2—C8—C7	122.43 (13)	C14—C13—H13B	109.2
N2—C8—S1	120.95 (10)	H13A—C13—H13B	107.9
C7—C8—S1	116.62 (10)	C4—C5—C6	120.31 (17)
C7—N1—C6	117.62 (12)	C4—C5—H5	119.8
C11—C10—S1	110.83 (10)	C6—C5—H5	119.8
C11—C10—H10A	109.5	C14—C15—C16	112.72 (16)
S1—C10—H10A	109.5	C14—C15—H15A	109.0
C11—C10—H10B	109.5	C16—C15—H15A	109.0
S1—C10—H10B	109.5	C14—C15—H15B	109.0
H10A—C10—H10B	108.1	C16—C15—H15B	109.0
N1—C7—C8	121.19 (13)	H15A—C15—H15B	107.8
N1—C7—C9	119.08 (12)	C7—C9—H9A	109.5
C8—C7—C9	119.73 (13)	C7—C9—H9B	109.5
N2—C1—C2	120.09 (13)	H9A—C9—H9B	109.5
N2—C1—C6	120.89 (13)	C7—C9—H9C	109.5
C2—C1—C6	119.02 (14)	H9A—C9—H9C	109.5
C10—C11—C12	111.23 (13)	H9B—C9—H9C	109.5
C10—C11—H11A	109.4	C3—C2—C1	119.96 (16)
C12—C11—H11A	109.4	C3—C2—H2	120.0
C10—C11—H11B	109.4	C1—C2—H2	120.0
C12—C11—H11B	109.4	C17—C16—C15	114.54 (18)
H11A—C11—H11B	108.0	C17—C16—H16A	108.6
N1—C6—C5	119.52 (14)	C15—C16—H16A	108.6
N1—C6—C1	121.03 (13)	C17—C16—H16B	108.6
C5—C6—C1	119.45 (14)	C15—C16—H16B	108.6
C13—C12—C11	115.33 (13)	H16A—C16—H16B	107.6
C13—C12—H12A	108.4	C2—C3—C4	121.23 (17)
C11—C12—H12A	108.4	C2—C3—H3	119.4
C13—C12—H12B	108.4	C4—C3—H3	119.4
C11—C12—H12B	108.4	C5—C4—C3	120.02 (17)
H12A—C12—H12B	107.5	C5—C4—H4	120.0
C15—C14—C13	115.44 (14)	C3—C4—H4	120.0
C15—C14—H14A	108.4	C16—C17—H17A	109.5
C13—C14—H14A	108.4	C16—C17—H17B	109.5
C15—C14—H14B	108.4	H17A—C17—H17B	109.5
C13—C14—H14B	108.4	C16—C17—H17C	109.5
H14A—C14—H14B	107.5	H17A—C17—H17C	109.5
C12—C13—C14	112.02 (13)	H17B—C17—H17C	109.5
C12—C13—H13A	109.2