3-[2-(3-Phenyl-2-oxo-1,2-di-hydro-quin-oxalin-1-yl)eth-yl]-1,3-oxazolidin-2-one.

The di-hydro-quinoxaline ring system of the title mol-ecule, C19H17N3O3, is approximately planar [maximum deviation = 0.050 (2) Å], the dihedral angle between the planes through the two fused rings being 4.75 (8)°. The mean plane through the fused-ring system forms a dihedral angle of 30.72 (5)° with the attached phenyl ring. The mol-ecular conformation is enforced by C-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For biochemical properties of quinoxaline derivatives, see: Seitz et al. (2002 ▶); Monge et al. (1993 ▶); Kim et al. (2004 ▶); Bailly et al. (1999 ▶). For a related structure, see: Caleb et al. (2009 ▶).

Experimental

Crystal data

C19H17N3O3

M = 335.36

Monoclinic,

a = 9.6314 (5) Å

b = 16.6596 (9) Å

c = 10.0749 (5) Å

β = 98.097 (3)°

V = 1600.46 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.43 × 0.31 × 0.19 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

23600 measured reflections

2249 independent reflections

1897 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 1.03

2249 reflections

226 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008702/rz5054sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008702/rz5054Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008702/rz5054Isup3.cml

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

C19H17N3O3	F(000) = 704
Mr = 335.36	Dx = 1.392 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2249 reflections
a = 9.6314 (5) Å	θ = 2.5–29.6°
b = 16.6596 (9) Å	µ = 0.10 mm−1
c = 10.0749 (5) Å	T = 296 K
β = 98.097 (3)°	Block, colourless
V = 1600.46 (14) Å3	0.43 × 0.31 × 0.19 mm
Z = 4

Bruker X8 APEXII area-detector diffractometer	1897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 29.6°, θmin = 2.5°
φ and ω scans	h = −13→13
23600 measured reflections	k = −23→23
2249 independent reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0647P)2] where P = (Fo2 + 2Fc2)/3
2249 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.21 e Å−3
2 restraints	Δρmin = −0.23 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
C19	0.0392 (3)	0.7294 (2)	0.3896 (3)	0.0830 (8)
H19A	−0.0057	0.7689	0.3270	0.100*
H19B	−0.0282	0.6876	0.4010	0.100*
C1	0.43510 (17)	0.88352 (11)	0.25887 (17)	0.0419 (4)
C2	0.3351 (2)	0.86112 (14)	0.1505 (2)	0.0560 (5)
H2	0.3144	0.8072	0.1337	0.067*
C3	0.2676 (2)	0.91989 (16)	0.0689 (2)	0.0646 (6)
H3	0.2029	0.9048	−0.0043	0.078*
C4	0.2938 (2)	1.00054 (15)	0.0931 (2)	0.0605 (5)
H4	0.2473	1.0391	0.0366	0.073*
C5	0.3888 (2)	1.02337 (13)	0.2009 (2)	0.0509 (4)
H5	0.4049	1.0776	0.2187	0.061*
C6	0.46138 (17)	0.96571 (11)	0.28424 (17)	0.0412 (4)
C7	0.63967 (16)	0.94028 (10)	0.45793 (17)	0.0391 (3)
C8	0.62007 (19)	0.85246 (11)	0.44060 (18)	0.0431 (4)
O1	0.69145 (17)	0.80218 (9)	0.50945 (16)	0.0599 (4)
C10	0.75182 (18)	0.97196 (11)	0.56143 (17)	0.0419 (4)
C11	0.8763 (2)	0.93092 (13)	0.6025 (2)	0.0548 (5)
H11	0.8910	0.8805	0.5672	0.066*
C12	0.9784 (2)	0.96538 (16)	0.6962 (2)	0.0686 (7)
H12	1.0618	0.9380	0.7232	0.082*
C13	0.9575 (3)	1.03972 (18)	0.7496 (2)	0.0726 (7)
H13	1.0261	1.0620	0.8131	0.087*
C14	0.8350 (3)	1.08113 (15)	0.7089 (2)	0.0611 (5)
H14	0.8211	1.1315	0.7446	0.073*
C15	0.73293 (19)	1.04777 (12)	0.61482 (18)	0.0469 (4)
H15	0.6509	1.0761	0.5869	0.056*
C16	0.4966 (2)	0.74090 (11)	0.3260 (2)	0.0530 (5)
H16A	0.5878	0.7160	0.3277	0.064*
H16B	0.4422	0.7298	0.2394	0.064*
C17	0.4230 (2)	0.70405 (11)	0.4355 (2)	0.0521 (4)
H17A	0.4252	0.6461	0.4274	0.063*
H17B	0.4744	0.7183	0.5221	0.063*
C18	0.1649 (2)	0.69463 (14)	0.3391 (2)	0.0576 (5)
H18A	0.1655	0.6365	0.3449	0.069*
H18B	0.1694	0.7106	0.2472	0.069*
C20	0.2316 (2)	0.76446 (12)	0.5358 (2)	0.0545 (5)
N1	0.51490 (16)	0.82872 (9)	0.34210 (15)	0.0436 (3)
N2	0.56282 (15)	0.99212 (10)	0.38580 (14)	0.0416 (3)
N3	0.27874 (17)	0.72966 (9)	0.43071 (16)	0.0467 (4)
O2	0.08945 (18)	0.76632 (12)	0.51602 (18)	0.0767 (5)
O3	0.2986 (2)	0.79160 (12)	0.63608 (19)	0.0801 (6)

	U11	U22	U33	U12	U13	U23
C19	0.0653 (14)	0.110 (2)	0.0686 (17)	0.0044 (14)	−0.0094 (12)	−0.0121 (15)
C1	0.0443 (8)	0.0411 (8)	0.0417 (9)	−0.0065 (7)	0.0114 (7)	0.0006 (7)
C2	0.0574 (11)	0.0558 (12)	0.0537 (11)	−0.0183 (9)	0.0032 (9)	−0.0057 (9)
C3	0.0538 (10)	0.0796 (16)	0.0563 (12)	−0.0125 (11)	−0.0068 (9)	−0.0055 (11)
C4	0.0517 (10)	0.0687 (14)	0.0571 (12)	0.0037 (9)	−0.0063 (8)	0.0067 (11)
C5	0.0475 (9)	0.0475 (10)	0.0559 (11)	0.0025 (8)	0.0012 (8)	0.0029 (9)
C6	0.0410 (7)	0.0402 (9)	0.0424 (9)	−0.0022 (6)	0.0061 (6)	−0.0014 (7)
C7	0.0432 (8)	0.0357 (8)	0.0392 (8)	−0.0023 (7)	0.0090 (6)	0.0009 (7)
C8	0.0517 (9)	0.0353 (8)	0.0435 (9)	−0.0028 (7)	0.0115 (7)	0.0030 (7)
O1	0.0708 (9)	0.0422 (7)	0.0644 (9)	0.0024 (7)	0.0011 (7)	0.0122 (7)
C10	0.0474 (8)	0.0434 (9)	0.0347 (8)	−0.0063 (7)	0.0053 (7)	0.0057 (7)
C11	0.0480 (10)	0.0546 (11)	0.0607 (12)	−0.0009 (8)	0.0040 (8)	0.0120 (9)
C12	0.0506 (11)	0.0777 (17)	0.0732 (16)	−0.0109 (10)	−0.0061 (10)	0.0246 (13)
C13	0.0643 (13)	0.0936 (19)	0.0548 (13)	−0.0329 (13)	−0.0094 (10)	0.0110 (12)
C14	0.0737 (13)	0.0649 (13)	0.0451 (10)	−0.0223 (11)	0.0098 (9)	−0.0058 (10)
C15	0.0530 (9)	0.0487 (10)	0.0398 (9)	−0.0074 (8)	0.0095 (7)	0.0011 (8)
C16	0.0737 (13)	0.0320 (8)	0.0562 (11)	−0.0098 (9)	0.0200 (9)	−0.0034 (8)
C17	0.0621 (11)	0.0377 (9)	0.0573 (11)	−0.0061 (8)	0.0112 (9)	0.0066 (8)
C18	0.0683 (12)	0.0614 (12)	0.0415 (10)	−0.0206 (10)	0.0018 (9)	−0.0036 (9)
C20	0.0671 (12)	0.0394 (9)	0.0548 (12)	0.0007 (8)	0.0007 (9)	−0.0078 (9)
N1	0.0541 (8)	0.0325 (7)	0.0453 (8)	−0.0067 (6)	0.0114 (6)	−0.0006 (6)
N2	0.0444 (7)	0.0377 (7)	0.0420 (7)	−0.0011 (5)	0.0038 (5)	−0.0014 (6)
N3	0.0574 (8)	0.0395 (7)	0.0420 (8)	−0.0105 (6)	0.0025 (6)	−0.0014 (6)
O2	0.0658 (9)	0.0893 (13)	0.0732 (12)	0.0139 (9)	0.0032 (8)	−0.0222 (10)
O3	0.0960 (13)	0.0695 (11)	0.0691 (11)	−0.0031 (9)	−0.0086 (9)	−0.0321 (9)

C19—O2	1.436 (3)	C11—C12	1.388 (3)
C19—C18	1.494 (4)	C11—H11	0.9300
C19—H19A	0.9700	C12—C13	1.376 (4)
C19—H19B	0.9700	C12—H12	0.9300
C1—N1	1.395 (2)	C13—C14	1.378 (4)
C1—C2	1.401 (2)	C13—H13	0.9300
C1—C6	1.409 (2)	C14—C15	1.382 (3)
C2—C3	1.381 (3)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.383 (4)	C16—N1	1.480 (2)
C3—H3	0.9300	C16—C17	1.521 (3)
C4—C5	1.371 (3)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C5—C6	1.397 (3)	C17—N3	1.448 (3)
C5—H5	0.9300	C17—H17A	0.9700
C6—N2	1.383 (2)	C17—H17B	0.9700
C7—N2	1.292 (2)	C18—N3	1.452 (2)
C7—C8	1.482 (2)	C18—H18A	0.9700
C7—C10	1.488 (2)	C18—H18B	0.9700
C8—O1	1.233 (2)	C20—O3	1.207 (3)
C8—N1	1.373 (2)	C20—N3	1.341 (3)
C10—C11	1.391 (3)	C20—O2	1.356 (3)
C10—C15	1.395 (3)
O2—C19—C18	106.27 (19)	C12—C13—C14	120.0 (2)
O2—C19—H19A	110.5	C12—C13—H13	120.0
C18—C19—H19A	110.5	C14—C13—H13	120.0
O2—C19—H19B	110.5	C13—C14—C15	119.9 (2)
C18—C19—H19B	110.5	C13—C14—H14	120.0
H19A—C19—H19B	108.7	C15—C14—H14	120.0
N1—C1—C2	123.65 (16)	C14—C15—C10	120.6 (2)
N1—C1—C6	117.21 (14)	C14—C15—H15	119.7
C2—C1—C6	119.10 (17)	C10—C15—H15	119.7
C3—C2—C1	119.32 (19)	N1—C16—C17	112.34 (17)
C3—C2—H2	120.3	N1—C16—H16A	109.1
C1—C2—H2	120.3	C17—C16—H16A	109.1
C2—C3—C4	121.64 (19)	N1—C16—H16B	109.1
C2—C3—H3	119.2	C17—C16—H16B	109.1
C4—C3—H3	119.2	H16A—C16—H16B	107.9
C5—C4—C3	119.6 (2)	N3—C17—C16	113.57 (17)
C5—C4—H4	120.2	N3—C17—H17A	108.9
C3—C4—H4	120.2	C16—C17—H17A	108.9
C4—C5—C6	120.45 (19)	N3—C17—H17B	108.9
C4—C5—H5	119.8	C16—C17—H17B	108.9
C6—C5—H5	119.8	H17A—C17—H17B	107.7
N2—C6—C5	117.88 (16)	N3—C18—C19	101.73 (18)
N2—C6—C1	122.23 (16)	N3—C18—H18A	111.4
C5—C6—C1	119.82 (16)	C19—C18—H18A	111.4
N2—C7—C8	122.68 (15)	N3—C18—H18B	111.4
N2—C7—C10	117.29 (15)	C19—C18—H18B	111.4
C8—C7—C10	120.03 (15)	H18A—C18—H18B	109.3
O1—C8—N1	120.46 (16)	O3—C20—N3	128.4 (2)
O1—C8—C7	123.54 (17)	O3—C20—O2	121.6 (2)
N1—C8—C7	116.00 (15)	N3—C20—O2	109.92 (17)
C11—C10—C15	118.96 (17)	C8—N1—C1	122.27 (13)
C11—C10—C7	122.94 (17)	C8—N1—C16	115.38 (15)
C15—C10—C7	118.04 (16)	C1—N1—C16	122.29 (15)
C12—C11—C10	119.8 (2)	C7—N2—C6	119.49 (14)
C12—C11—H11	120.1	C20—N3—C17	122.08 (16)
C10—C11—H11	120.1	C20—N3—C18	111.48 (17)
C13—C12—C11	120.6 (2)	C17—N3—C18	122.53 (17)
C13—C12—H12	119.7	C20—O2—C19	109.14 (19)
C11—C12—H12	119.7

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1	0.93	2.33	2.860 (3)	116
C17—H17B···O1	0.97	2.53	3.061 (2)	114
C2—H2···O1i	0.93	2.42	3.283 (3)	154
C5—H5···O3ii	0.93	2.50	3.244 (3)	137
C18—H18B···O1i	0.97	2.44	3.367 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1	0.93	2.33	2.860 (3)	116
C17—H17B⋯O1	0.97	2.53	3.061 (2)	114
C2—H2⋯O1i	0.93	2.42	3.283 (3)	154
C5—H5⋯O3ii	0.93	2.50	3.244 (3)	137
C18—H18B⋯O1i	0.97	2.44	3.367 (3)	159

Symmetry codes: (i) ; (ii) .