4-[2-(Benzyl-sulfan-yl)acet-yl]-3,4-dihydro-quinoxalin-2(1H)-one.

In the title compound, C(17)H(16)N(2)O(2)S, the pyrazinone ring is non-planar (r.m.s. deviation = 0.1595 Å), with maximum deviations for the 4-position N atom and the adjacent non-fused-ring C atom of 0.2557 (15) and -0.2118 (16) Å, respectively. The dihedral angle between the benzyl ring and pyrazinone rings is 30.45 (18)°. Inter-molecular N-H⋯O hydrogen-bonding inter-actions forms inversion dimers which lead to eight-membered R(2) (2)(8) ring motifs. The dimers are further connected by C-H⋯O inter-actions.

Related literature

For the biological activity of quinoxalines, see: Ali et al. (2000 ▶); Moustafa & Yameda (2001 ▶). For related structures see: Nasir et al. (2009) ▶. For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H16N2O2S

M = 312.38

Orthorhombic,

a = 13.9502 (8) Å

b = 32.2588 (17) Å

c = 6.9728 (3) Å

V = 3137.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.47 × 0.23 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.906, T max = 0.985

16363 measured reflections

3892 independent reflections

2412 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.183

S = 1.00

3889 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008178/hg2799sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008178/hg2799Isup2.hkl

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

C17H16N2O2S	F(000) = 1312
Mr = 312.38	Dx = 1.322 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2915 reflections
a = 13.9502 (8) Å	θ = 3.2–23.1°
b = 32.2588 (17) Å	µ = 0.22 mm−1
c = 6.9728 (3) Å	T = 296 K
V = 3137.9 (3) Å3	Plate, colorless
Z = 8	0.47 × 0.23 × 0.07 mm

Bruker Kappa APEXII CCD diffractometer	3892 independent reflections
Radiation source: fine-focus sealed tube	2412 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −18→17
Tmin = 0.906, Tmax = 0.985	k = −23→43
16363 measured reflections	l = −9→9

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.108P)2 + 0.1052P] where P = (Fo2 + 2Fc2)/3
3889 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.67947 (5)	0.701430 (18)	0.13947 (11)	0.0539 (3)
O4	0.77529 (11)	0.61610 (5)	0.1173 (2)	0.0439 (4)
N1	0.63517 (13)	0.58234 (5)	0.0968 (3)	0.0364 (4)
O3	0.63199 (12)	0.50899 (5)	0.4824 (2)	0.0530 (5)
C1	0.47960 (15)	0.55216 (6)	0.1309 (3)	0.0377 (5)
C9	0.69061 (15)	0.61743 (6)	0.0743 (3)	0.0331 (5)
C8	0.60499 (16)	0.52927 (7)	0.3446 (3)	0.0399 (5)
C7	0.67595 (15)	0.54813 (7)	0.2064 (3)	0.0400 (5)
H7A	0.7311	0.5581	0.2775	0.048*
H7B	0.6980	0.5269	0.1184	0.048*
N2	0.51165 (14)	0.53532 (6)	0.3046 (3)	0.0442 (5)
C10	0.64388 (16)	0.65674 (7)	0.0037 (3)	0.0394 (5)
H10A	0.5748	0.6537	0.0112	0.047*
H10B	0.6607	0.6610	−0.1299	0.047*
C5	0.51272 (19)	0.58963 (8)	−0.1586 (4)	0.0490 (6)
H5	0.5557	0.6032	−0.2391	0.059*
C12	0.50134 (19)	0.69134 (8)	0.3071 (4)	0.0514 (6)
C6	0.54236 (15)	0.57563 (6)	0.0199 (3)	0.0364 (5)
C3	0.35632 (19)	0.56161 (9)	−0.1015 (4)	0.0581 (7)
H3	0.2931	0.5579	−0.1402	0.070*
C2	0.38689 (17)	0.54535 (7)	0.0697 (4)	0.0477 (6)
H2	0.3451	0.5297	0.1445	0.057*
C11	0.6058 (2)	0.69568 (9)	0.3512 (4)	0.0577 (7)
H11A	0.6269	0.6714	0.4217	0.069*
H11B	0.6150	0.7197	0.4332	0.069*
C4	0.4191 (2)	0.58341 (8)	−0.2165 (4)	0.0592 (7)
H4	0.3983	0.5940	−0.3334	0.071*
C13	0.4534 (3)	0.65588 (11)	0.3446 (5)	0.0776 (9)
H13	0.4853	0.6339	0.4025	0.093*
C16	0.3583 (3)	0.7183 (2)	0.1691 (9)	0.156 (3)
H16	0.3267	0.7396	0.1054	0.188*
C14	0.3569 (3)	0.65185 (15)	0.2976 (7)	0.1123 (16)
H14	0.3240	0.6275	0.3254	0.135*
C17	0.4533 (2)	0.72278 (13)	0.2194 (7)	0.1095 (15)
H17	0.4849	0.7475	0.1932	0.131*
C15	0.3119 (3)	0.6836 (2)	0.2115 (7)	0.133 (2)
H15	0.2473	0.6812	0.1811	0.160*
H1N	0.471 (2)	0.5207 (9)	0.367 (4)	0.060 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0418 (4)	0.0307 (3)	0.0892 (6)	−0.0038 (2)	0.0018 (3)	−0.0011 (3)
O4	0.0330 (9)	0.0376 (8)	0.0611 (10)	−0.0068 (7)	−0.0027 (7)	0.0045 (7)
N1	0.0310 (10)	0.0358 (10)	0.0424 (10)	−0.0056 (8)	−0.0005 (8)	0.0066 (8)
O3	0.0451 (10)	0.0577 (11)	0.0561 (11)	−0.0119 (8)	−0.0068 (8)	0.0193 (9)
C1	0.0321 (11)	0.0339 (11)	0.0473 (13)	−0.0016 (9)	0.0012 (10)	0.0006 (10)
C9	0.0322 (11)	0.0316 (10)	0.0356 (11)	−0.0031 (9)	0.0043 (9)	−0.0004 (9)
C8	0.0380 (12)	0.0360 (11)	0.0456 (13)	−0.0075 (10)	0.0005 (10)	0.0048 (10)
C7	0.0315 (11)	0.0358 (11)	0.0527 (13)	−0.0028 (9)	0.0015 (10)	0.0092 (10)
N2	0.0336 (11)	0.0494 (11)	0.0495 (12)	−0.0061 (9)	0.0057 (9)	0.0140 (10)
C10	0.0355 (12)	0.0381 (12)	0.0447 (12)	−0.0009 (10)	0.0063 (10)	0.0042 (10)
C5	0.0462 (15)	0.0544 (15)	0.0464 (14)	−0.0109 (12)	−0.0015 (11)	0.0093 (11)
C12	0.0476 (15)	0.0572 (15)	0.0495 (14)	0.0108 (12)	0.0027 (11)	−0.0060 (12)
C6	0.0302 (11)	0.0332 (10)	0.0459 (12)	−0.0037 (9)	−0.0009 (9)	−0.0002 (9)
C3	0.0391 (13)	0.0587 (16)	0.0765 (19)	−0.0109 (13)	−0.0155 (13)	−0.0009 (14)
C2	0.0338 (12)	0.0452 (13)	0.0642 (16)	−0.0086 (11)	0.0019 (11)	0.0022 (12)
C11	0.0540 (17)	0.0592 (16)	0.0599 (16)	0.0099 (13)	−0.0070 (13)	−0.0154 (13)
C4	0.0557 (17)	0.0663 (17)	0.0558 (16)	−0.0097 (14)	−0.0181 (13)	0.0063 (13)
C13	0.068 (2)	0.075 (2)	0.090 (2)	−0.0013 (18)	0.0167 (18)	−0.0014 (18)
C16	0.062 (3)	0.211 (6)	0.197 (6)	0.044 (3)	0.011 (3)	0.093 (5)
C14	0.076 (3)	0.135 (4)	0.126 (4)	−0.044 (3)	0.031 (3)	−0.041 (3)
C17	0.053 (2)	0.099 (3)	0.176 (4)	0.028 (2)	0.007 (2)	0.054 (3)
C15	0.050 (2)	0.241 (7)	0.109 (4)	0.011 (3)	−0.010 (2)	−0.007 (4)

S1—C10	1.795 (2)	C5—H5	0.9300
S1—C11	1.808 (3)	C12—C13	1.351 (4)
O4—C9	1.219 (3)	C12—C17	1.361 (4)
N1—C9	1.380 (3)	C12—C11	1.496 (4)
N1—C6	1.418 (3)	C3—C2	1.372 (4)
N1—C7	1.458 (3)	C3—C4	1.380 (4)
O3—C8	1.222 (3)	C3—H3	0.9300
C1—C2	1.380 (3)	C2—H2	0.9300
C1—C6	1.393 (3)	C11—H11A	0.9700
C1—N2	1.400 (3)	C11—H11B	0.9700
C9—C10	1.508 (3)	C4—H4	0.9300
C8—N2	1.346 (3)	C13—C14	1.392 (5)
C8—C7	1.509 (3)	C13—H13	0.9300
C7—H7A	0.9700	C16—C15	1.327 (8)
C7—H7B	0.9700	C16—C17	1.379 (6)
N2—H1N	0.85 (3)	C16—H16	0.9300
C10—H10A	0.9700	C14—C15	1.342 (7)
C10—H10B	0.9700	C14—H14	0.9300
C5—C4	1.382 (4)	C17—H17	0.9300
C5—C6	1.387 (3)	C15—H15	0.9300
C10—S1—C11	101.02 (12)	C5—C6—C1	119.2 (2)
C9—N1—C6	126.45 (18)	C5—C6—N1	124.2 (2)
C9—N1—C7	117.51 (17)	C1—C6—N1	116.55 (19)
C6—N1—C7	116.03 (17)	C2—C3—C4	120.2 (2)
C2—C1—C6	120.3 (2)	C2—C3—H3	119.9
C2—C1—N2	120.3 (2)	C4—C3—H3	119.9
C6—C1—N2	119.4 (2)	C3—C2—C1	120.0 (2)
O4—C9—N1	119.08 (19)	C3—C2—H2	120.0
O4—C9—C10	121.91 (19)	C1—C2—H2	120.0
N1—C9—C10	118.98 (19)	C12—C11—S1	113.29 (19)
O3—C8—N2	122.6 (2)	C12—C11—H11A	108.9
O3—C8—C7	121.0 (2)	S1—C11—H11A	108.9
N2—C8—C7	116.3 (2)	C12—C11—H11B	108.9
N1—C7—C8	112.57 (18)	S1—C11—H11B	108.9
N1—C7—H7A	109.1	H11A—C11—H11B	107.7
C8—C7—H7A	109.1	C3—C4—C5	120.3 (3)
N1—C7—H7B	109.1	C3—C4—H4	119.9
C8—C7—H7B	109.1	C5—C4—H4	119.9
H7A—C7—H7B	107.8	C12—C13—C14	120.8 (4)
C8—N2—C1	123.0 (2)	C12—C13—H13	119.6
C8—N2—H1N	117.0 (19)	C14—C13—H13	119.6
C1—N2—H1N	116.3 (19)	C15—C16—C17	120.0 (5)
C9—C10—S1	112.54 (16)	C15—C16—H16	120.0
C9—C10—H10A	109.1	C17—C16—H16	120.0
S1—C10—H10A	109.1	C15—C14—C13	119.1 (4)
C9—C10—H10B	109.1	C15—C14—H14	120.4
S1—C10—H10B	109.1	C13—C14—H14	120.4
H10A—C10—H10B	107.8	C12—C17—C16	120.7 (4)
C4—C5—C6	119.8 (2)	C12—C17—H17	119.7
C4—C5—H5	120.1	C16—C17—H17	119.7
C6—C5—H5	120.1	C16—C15—C14	121.1 (4)
C13—C12—C17	118.3 (3)	C16—C15—H15	119.5
C13—C12—C11	121.4 (3)	C14—C15—H15	119.5
C17—C12—C11	120.2 (3)
C6—N1—C9—O4	−166.4 (2)	C9—N1—C6—C5	36.4 (3)
C7—N1—C9—O4	12.1 (3)	C7—N1—C6—C5	−142.1 (2)
C6—N1—C9—C10	15.7 (3)	C9—N1—C6—C1	−145.9 (2)
C7—N1—C9—C10	−165.86 (19)	C7—N1—C6—C1	35.6 (3)
C9—N1—C7—C8	136.4 (2)	C4—C3—C2—C1	2.5 (4)
C6—N1—C7—C8	−44.9 (3)	C6—C1—C2—C3	0.2 (4)
O3—C8—C7—N1	−159.2 (2)	N2—C1—C2—C3	−179.4 (2)
N2—C8—C7—N1	22.2 (3)	C13—C12—C11—S1	114.1 (3)
O3—C8—N2—C1	−168.6 (2)	C17—C12—C11—S1	−62.9 (4)
C7—C8—N2—C1	10.0 (3)	C10—S1—C11—C12	−54.1 (2)
C2—C1—N2—C8	158.4 (2)	C2—C3—C4—C5	−1.1 (4)
C6—C1—N2—C8	−21.2 (3)	C6—C5—C4—C3	−3.1 (4)
O4—C9—C10—S1	−43.2 (3)	C17—C12—C13—C14	−1.1 (5)
N1—C9—C10—S1	134.71 (18)	C11—C12—C13—C14	−178.1 (3)
C11—S1—C10—C9	−78.50 (18)	C12—C13—C14—C15	1.0 (6)
C4—C5—C6—C1	5.8 (4)	C13—C12—C17—C16	−0.4 (6)
C4—C5—C6—N1	−176.6 (2)	C11—C12—C17—C16	176.6 (4)
C2—C1—C6—C5	−4.4 (3)	C15—C16—C17—C12	2.1 (9)
N2—C1—C6—C5	175.2 (2)	C17—C16—C15—C14	−2.3 (10)
C2—C1—C6—N1	177.8 (2)	C13—C14—C15—C16	0.7 (8)
N2—C1—C6—N1	−2.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.93	2.60	3.452 (3)	153
C10—H10B···O4i	0.97	2.45	3.202 (3)	134
N2—H1N···O3ii	0.85 (3)	2.02 (3)	2.875 (3)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.93	2.60	3.452 (3)	153
C10—H10B⋯O4i	0.97	2.45	3.202 (3)	134
N2—H1N⋯O3ii	0.85 (3)	2.02 (3)	2.875 (3)	175 (3)

Symmetry codes: (i) ; (ii) .