4-[(2,5-Dimethyl-anilino)acet-yl]-3,4-di-hydro-quinoxalin-2(1H)-one.

In the title compound, C(18)H(19)N(3)O(2), the dihedral angle between the benzene rings is 20.47 (10)° and an intra-molecular N-H⋯O hydrogen bond occurs, generating an S(5) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds lead to R(2) (2)(8) loops.

Related literature

For background to the biological activity of quinoxalines, see: Khan (2008 ▶); Miyashiro et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H19N3O2

M = 309.36

Triclinic,

a = 5.3806 (2) Å

b = 12.3580 (6) Å

c = 13.2812 (6) Å

α = 62.878 (2)°

β = 84.135 (2)°

γ = 80.835 (3)°

V = 775.53 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.38 × 0.17 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.967, T max = 0.995

16710 measured reflections

3803 independent reflections

2277 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.02

3803 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 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 (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/S1600536809045991/hb5210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045991/hb5210Isup2.hkl

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

C18H19N3O2	Z = 2
Mr = 309.36	F(000) = 328
Triclinic, P1	Dx = 1.325 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3806 (2) Å	Cell parameters from 3605 reflections
b = 12.3580 (6) Å	θ = 3.1–25.1°
c = 13.2812 (6) Å	µ = 0.09 mm−1
α = 62.878 (2)°	T = 296 K
β = 84.135 (2)°	Chunk, colourless
γ = 80.835 (3)°	0.38 × 0.17 × 0.06 mm
V = 775.53 (6) Å3

Bruker Kappa APEXII CCD diffractometer	3803 independent reflections
Radiation source: fine-focus sealed tube	2277 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→7
Tmin = 0.967, Tmax = 0.995	k = −16→16
16710 measured reflections	l = −17→17

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1485P] where P = (Fo2 + 2Fc2)/3
3803 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 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
C1	0.3267 (3)	−0.03248 (15)	0.21118 (13)	0.0375 (4)
C2	0.2304 (3)	−0.09075 (17)	0.15875 (15)	0.0474 (4)
H2	0.2528	−0.0632	0.0809	0.057*
C3	0.1012 (4)	−0.18983 (18)	0.22234 (17)	0.0565 (5)
H3	0.0350	−0.2283	0.1870	0.068*
C4	0.0695 (4)	−0.23204 (18)	0.33759 (17)	0.0595 (5)
H4	−0.0191	−0.2984	0.3798	0.071*
C5	0.1690 (3)	−0.17607 (17)	0.39049 (15)	0.0527 (5)
H5	0.1486	−0.2050	0.4685	0.063*
C6	0.2993 (3)	−0.07679 (15)	0.32755 (13)	0.0402 (4)
C7	0.5923 (3)	0.04788 (16)	0.33477 (14)	0.0432 (4)
C8	0.6625 (3)	0.07691 (18)	0.21398 (13)	0.0478 (5)
H8A	0.7148	0.1581	0.1760	0.057*
H8B	0.8051	0.0190	0.2119	0.057*
C9	0.3822 (3)	0.16519 (16)	0.05055 (13)	0.0394 (4)
C10	0.5334 (3)	0.27254 (16)	−0.00272 (13)	0.0441 (4)
H10A	0.5118	0.3170	0.0424	0.053*
H10B	0.7110	0.2433	−0.0060	0.053*
C11	0.5571 (3)	0.45478 (16)	−0.18728 (14)	0.0446 (4)
C12	0.4976 (3)	0.51241 (17)	−0.30190 (15)	0.0487 (4)
C13	0.6002 (4)	0.61824 (19)	−0.37152 (17)	0.0605 (5)
H13	0.5629	0.6575	−0.4478	0.073*
C14	0.7563 (4)	0.66854 (19)	−0.33251 (18)	0.0630 (6)
H14	0.8178	0.7415	−0.3819	0.076*
C15	0.8211 (3)	0.61092 (17)	−0.22080 (17)	0.0521 (5)
C16	0.7209 (3)	0.50364 (17)	−0.14910 (15)	0.0487 (4)
H16	0.7643	0.4633	−0.0735	0.058*
C17	0.9978 (4)	0.6614 (2)	−0.1771 (2)	0.0713 (6)
H17A	0.9490	0.6454	−0.1005	0.107*
H17B	0.9907	0.7483	−0.2235	0.107*
H17C	1.1664	0.6229	−0.1795	0.107*
C18	0.3267 (4)	0.4598 (2)	−0.34590 (16)	0.0609 (5)
H18A	0.3982	0.3782	−0.3324	0.091*
H18B	0.3080	0.5101	−0.4257	0.091*
H18C	0.1648	0.4573	−0.3077	0.091*
N1	0.4033 (3)	−0.02041 (14)	0.38128 (12)	0.0479 (4)
N2	0.4571 (2)	0.07258 (12)	0.15222 (11)	0.0388 (3)
N3	0.4475 (3)	0.35148 (15)	−0.11433 (13)	0.0580 (5)
O1	0.7078 (2)	0.08343 (13)	0.38634 (10)	0.0589 (4)
O2	0.2018 (2)	0.16278 (12)	0.00335 (10)	0.0550 (4)
H1N	0.366 (4)	−0.0432 (18)	0.4561 (19)	0.066*
H2N	0.339 (4)	0.3255 (19)	−0.1377 (17)	0.066*

	U11	U22	U33	U12	U13	U23
C1	0.0355 (8)	0.0409 (9)	0.0372 (9)	−0.0074 (7)	−0.0020 (6)	−0.0174 (7)
C2	0.0535 (10)	0.0532 (11)	0.0437 (10)	−0.0114 (8)	−0.0022 (8)	−0.0272 (9)
C3	0.0680 (12)	0.0528 (11)	0.0600 (12)	−0.0194 (10)	−0.0072 (9)	−0.0305 (10)
C4	0.0696 (13)	0.0527 (12)	0.0557 (12)	−0.0274 (10)	−0.0070 (10)	−0.0167 (10)
C5	0.0595 (11)	0.0560 (12)	0.0393 (10)	−0.0209 (9)	−0.0047 (8)	−0.0137 (9)
C6	0.0400 (9)	0.0454 (10)	0.0383 (9)	−0.0101 (7)	−0.0055 (7)	−0.0191 (8)
C7	0.0443 (9)	0.0476 (10)	0.0390 (9)	−0.0101 (8)	−0.0091 (7)	−0.0175 (8)
C8	0.0396 (9)	0.0648 (12)	0.0395 (10)	−0.0183 (8)	−0.0044 (7)	−0.0194 (9)
C9	0.0400 (9)	0.0481 (10)	0.0342 (9)	−0.0092 (7)	−0.0001 (7)	−0.0211 (8)
C10	0.0457 (9)	0.0514 (11)	0.0371 (9)	−0.0142 (8)	−0.0029 (7)	−0.0187 (8)
C11	0.0459 (10)	0.0438 (10)	0.0424 (10)	−0.0066 (8)	−0.0030 (7)	−0.0173 (8)
C12	0.0508 (10)	0.0496 (11)	0.0418 (10)	−0.0020 (8)	−0.0040 (8)	−0.0181 (8)
C13	0.0656 (13)	0.0581 (12)	0.0431 (11)	−0.0049 (10)	−0.0028 (9)	−0.0106 (9)
C14	0.0669 (13)	0.0493 (12)	0.0608 (13)	−0.0165 (10)	0.0107 (10)	−0.0142 (10)
C15	0.0487 (10)	0.0501 (11)	0.0614 (12)	−0.0123 (8)	0.0078 (9)	−0.0284 (10)
C16	0.0520 (10)	0.0515 (11)	0.0437 (10)	−0.0136 (9)	−0.0019 (8)	−0.0200 (9)
C17	0.0663 (13)	0.0734 (15)	0.0898 (17)	−0.0316 (11)	0.0121 (12)	−0.0459 (13)
C18	0.0656 (12)	0.0696 (14)	0.0475 (11)	−0.0066 (10)	−0.0132 (9)	−0.0247 (10)
N1	0.0548 (9)	0.0629 (10)	0.0327 (8)	−0.0240 (8)	0.0006 (6)	−0.0224 (7)
N2	0.0381 (7)	0.0471 (8)	0.0331 (7)	−0.0131 (6)	−0.0024 (5)	−0.0169 (6)
N3	0.0679 (11)	0.0545 (10)	0.0456 (9)	−0.0250 (8)	−0.0165 (8)	−0.0090 (8)
O1	0.0667 (8)	0.0757 (9)	0.0453 (7)	−0.0334 (7)	−0.0050 (6)	−0.0283 (7)
O2	0.0546 (7)	0.0619 (8)	0.0449 (7)	−0.0206 (6)	−0.0148 (6)	−0.0140 (6)

C1—C6	1.385 (2)	C10—H10A	0.9700
C1—C2	1.386 (2)	C10—H10B	0.9700
C1—N2	1.4290 (19)	C11—N3	1.383 (2)
C2—C3	1.380 (2)	C11—C16	1.392 (2)
C2—H2	0.9300	C11—C12	1.402 (2)
C3—C4	1.375 (3)	C12—C13	1.376 (3)
C3—H3	0.9300	C12—C18	1.502 (2)
C4—C5	1.377 (2)	C13—C14	1.382 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.384 (2)	C14—C15	1.376 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—N1	1.402 (2)	C15—C16	1.388 (2)
C7—O1	1.2233 (18)	C15—C17	1.504 (3)
C7—N1	1.341 (2)	C16—H16	0.9300
C7—C8	1.496 (2)	C17—H17A	0.9600
C8—N2	1.4632 (18)	C17—H17B	0.9600
C8—H8A	0.9700	C17—H17C	0.9600
C8—H8B	0.9700	C18—H18A	0.9600
C9—O2	1.2192 (17)	C18—H18B	0.9600
C9—N2	1.361 (2)	C18—H18C	0.9600
C9—C10	1.514 (2)	N1—H1N	0.91 (2)
C10—N3	1.429 (2)	N3—H2N	0.85 (2)
C6—C1—C2	119.61 (15)	C16—C11—C12	119.56 (16)
C6—C1—N2	116.51 (13)	C13—C12—C11	117.64 (17)
C2—C1—N2	123.89 (15)	C13—C12—C18	121.72 (17)
C3—C2—C1	119.81 (16)	C11—C12—C18	120.64 (16)
C3—C2—H2	120.1	C12—C13—C14	122.58 (18)
C1—C2—H2	120.1	C12—C13—H13	118.7
C4—C3—C2	120.47 (16)	C14—C13—H13	118.7
C4—C3—H3	119.8	C15—C14—C13	120.20 (18)
C2—C3—H3	119.8	C15—C14—H14	119.9
C3—C4—C5	120.01 (17)	C13—C14—H14	119.9
C3—C4—H4	120.0	C14—C15—C16	118.20 (17)
C5—C4—H4	120.0	C14—C15—C17	121.24 (18)
C4—C5—C6	119.99 (17)	C16—C15—C17	120.56 (18)
C4—C5—H5	120.0	C15—C16—C11	121.77 (17)
C6—C5—H5	120.0	C15—C16—H16	119.1
C5—C6—C1	120.08 (15)	C11—C16—H16	119.1
C5—C6—N1	120.15 (15)	C15—C17—H17A	109.5
C1—C6—N1	119.77 (14)	C15—C17—H17B	109.5
O1—C7—N1	123.53 (16)	H17A—C17—H17B	109.5
O1—C7—C8	120.51 (15)	C15—C17—H17C	109.5
N1—C7—C8	115.94 (14)	H17A—C17—H17C	109.5
N2—C8—C7	113.34 (13)	H17B—C17—H17C	109.5
N2—C8—H8A	108.9	C12—C18—H18A	109.5
C7—C8—H8A	108.9	C12—C18—H18B	109.5
N2—C8—H8B	108.9	H18A—C18—H18B	109.5
C7—C8—H8B	108.9	C12—C18—H18C	109.5
H8A—C8—H8B	107.7	H18A—C18—H18C	109.5
O2—C9—N2	122.03 (15)	H18B—C18—H18C	109.5
O2—C9—C10	120.83 (15)	C7—N1—C6	122.90 (15)
N2—C9—C10	117.14 (13)	C7—N1—H1N	116.9 (12)
N3—C10—C9	108.72 (12)	C6—N1—H1N	118.9 (12)
N3—C10—H10A	109.9	C9—N2—C1	122.08 (12)
C9—C10—H10A	109.9	C9—N2—C8	123.03 (13)
N3—C10—H10B	109.9	C1—N2—C8	114.71 (13)
C9—C10—H10B	109.9	C11—N3—C10	122.78 (14)
H10A—C10—H10B	108.3	C11—N3—H2N	120.7 (14)
N3—C11—C16	121.54 (16)	C10—N3—H2N	115.9 (14)
N3—C11—C12	118.89 (16)
C6—C1—C2—C3	2.1 (3)	C13—C14—C15—C17	177.88 (19)
N2—C1—C2—C3	−178.28 (16)	C14—C15—C16—C11	−0.6 (3)
C1—C2—C3—C4	−0.7 (3)	C17—C15—C16—C11	−179.95 (17)
C2—C3—C4—C5	−0.6 (3)	N3—C11—C16—C15	−176.58 (18)
C3—C4—C5—C6	0.5 (3)	C12—C11—C16—C15	2.3 (3)
C4—C5—C6—C1	0.9 (3)	O1—C7—N1—C6	−169.54 (17)
C4—C5—C6—N1	−179.29 (17)	C8—C7—N1—C6	8.9 (3)
C2—C1—C6—C5	−2.2 (3)	C5—C6—N1—C7	158.51 (17)
N2—C1—C6—C5	178.14 (15)	C1—C6—N1—C7	−21.7 (3)
C2—C1—C6—N1	178.03 (16)	O2—C9—N2—C1	−1.1 (3)
N2—C1—C6—N1	−1.6 (2)	C10—C9—N2—C1	179.09 (14)
O1—C7—C8—N2	−157.17 (17)	O2—C9—N2—C8	−175.90 (16)
N1—C7—C8—N2	24.4 (2)	C10—C9—N2—C8	4.3 (2)
O2—C9—C10—N3	−7.3 (2)	C6—C1—N2—C9	−140.30 (16)
N2—C9—C10—N3	172.49 (15)	C2—C1—N2—C9	40.0 (2)
N3—C11—C12—C13	177.03 (18)	C6—C1—N2—C8	34.9 (2)
C16—C11—C12—C13	−1.9 (3)	C2—C1—N2—C8	−144.75 (17)
N3—C11—C12—C18	−2.7 (3)	C7—C8—N2—C9	129.03 (17)
C16—C11—C12—C18	178.41 (17)	C7—C8—N2—C1	−46.1 (2)
C11—C12—C13—C14	−0.2 (3)	C16—C11—N3—C10	−14.3 (3)
C18—C12—C13—C14	179.55 (19)	C12—C11—N3—C10	166.82 (18)
C12—C13—C14—C15	1.9 (3)	C9—C10—N3—C11	−176.65 (17)
C13—C14—C15—C16	−1.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H2N···O2	0.85 (2)	2.20 (2)	2.620 (2)	110.0 (16)
N1—H1N···O1i	0.91 (2)	1.93 (2)	2.8405 (19)	176.9 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H2N⋯O2	0.85 (2)	2.20 (2)	2.620 (2)	110.0 (16)
N1—H1N⋯O1i	0.91 (2)	1.93 (2)	2.8405 (19)	176.9 (18)

Symmetry code: (i) .