2-[3-(2-Acetoxyphenyl)quinoxa-lin-2-yl]phenyl acetate.

The title compound, C24H18N2O4, crystallizes as a syn-conformer, with dihedral angles between the quinoxaline moiety and the acet-oxy-substituted benzene rings of 53.46 (3)° and 54.78 (3)°. In the crystal, the mol-ecules form chains along [100] via C-H⋯O inter-actions.

Related literature

For general background to quinoxaline derivatives, see: Brasche & Buchwald (2008 ▶); Do & Daugulis (2008 ▶); He et al. (2003 ▶); Kim et al. (2004 ▶); Lyons & Sanford (2010 ▶). For quinoxaline-directed C—H activation, see: Reddy et al. (2011 ▶). For a related structure, see: Rajnikant et al. (2006 ▶).

Experimental

Crystal data

C24H18N2O4

M = 398.40

Monoclinic,

a = 9.5723 (5) Å

b = 16.7309 (8) Å

c = 13.0555 (6) Å

β = 92.929 (2)°

V = 2088.15 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.48 × 0.46 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.959, T max = 0.983

15632 measured reflections

3646 independent reflections

2553 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.117

S = 1.00

3646 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009161/ld2099sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009161/ld2099Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009161/ld2099Isup3.cml

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

C24H18N2O4	F(000) = 832
Mr = 398.40	Dx = 1.267 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11299 reflections
a = 9.5723 (5) Å	θ = 3.1–27.4°
b = 16.7309 (8) Å	µ = 0.09 mm−1
c = 13.0555 (6) Å	T = 296 K
β = 92.929 (2)°	Platelet, yellow
V = 2088.15 (18) Å3	0.48 × 0.46 × 0.20 mm
Z = 4

Rigaku R-AXIS RAPID/ZJUG diffractometer	3646 independent reflections
Radiation source: rotating anode	2553 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 10.00 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
Tmin = 0.959, Tmax = 0.983	l = −15→15
15632 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.045P)2 + 0.7545P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
3646 reflections	Δρmax = 0.17 e Å−3
274 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (2)

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
C1	0.57616 (19)	0.12138 (11)	0.27152 (13)	0.0401 (4)
C2	0.7311 (2)	0.02174 (11)	0.31884 (15)	0.0467 (5)
C3	0.7625 (3)	−0.04950 (13)	0.37296 (19)	0.0678 (6)
H3	0.6940	−0.0747	0.4093	0.081*
C4	0.8934 (3)	−0.08127 (15)	0.3718 (2)	0.0778 (7)
H4	0.9141	−0.1280	0.4080	0.093*
C5	0.9964 (3)	−0.04432 (15)	0.3169 (2)	0.0783 (7)
H5	1.0850	−0.0671	0.3166	0.094*
C6	0.9699 (2)	0.02435 (14)	0.2639 (2)	0.0704 (7)
H6	1.0394	0.0480	0.2270	0.085*
C7	0.8360 (2)	0.05939 (12)	0.26533 (15)	0.0494 (5)
C8	0.68513 (19)	0.16210 (11)	0.22108 (14)	0.0429 (5)
C9	0.43173 (19)	0.15473 (11)	0.27655 (14)	0.0438 (5)
C10	0.3759 (2)	0.16739 (13)	0.37183 (17)	0.0586 (6)
H10	0.4290	0.1545	0.4312	0.070*
C11	0.2436 (3)	0.19857 (15)	0.3797 (2)	0.0714 (7)
H11	0.2083	0.2068	0.4439	0.086*
C12	0.1641 (2)	0.21744 (15)	0.2926 (2)	0.0731 (7)
H12	0.0751	0.2389	0.2980	0.088*
C13	0.2152 (2)	0.20474 (14)	0.19734 (19)	0.0628 (6)
H13	0.1610	0.2171	0.1383	0.075*
C14	0.3478 (2)	0.17335 (12)	0.19050 (15)	0.0473 (5)
C15	0.3570 (3)	0.09580 (15)	0.04113 (19)	0.0727 (7)
C16	0.4121 (3)	0.09362 (19)	−0.0632 (2)	0.0940 (9)
H16A	0.3871	0.0438	−0.0956	0.141*
H16B	0.5121	0.0987	−0.0581	0.141*
H16C	0.3727	0.1369	−0.1033	0.141*
C17	0.66704 (19)	0.24376 (11)	0.17661 (15)	0.0432 (5)
C18	0.6188 (2)	0.30646 (12)	0.23494 (17)	0.0537 (5)
H18	0.5930	0.2967	0.3015	0.064*
C19	0.6084 (2)	0.38308 (13)	0.19573 (19)	0.0622 (6)
H19	0.5755	0.4244	0.2357	0.075*
C20	0.6466 (2)	0.39806 (14)	0.09761 (19)	0.0650 (6)
H20	0.6390	0.4495	0.0710	0.078*
C21	0.6961 (2)	0.33717 (13)	0.03828 (17)	0.0577 (6)
H21	0.7231	0.3475	−0.0279	0.069*
C22	0.70544 (19)	0.26088 (11)	0.07788 (15)	0.0448 (5)
C23	0.8838 (2)	0.19247 (13)	−0.00467 (16)	0.0554 (5)
C24	0.9139 (3)	0.11638 (17)	−0.0569 (2)	0.0940 (9)
H24A	1.0092	0.1164	−0.0765	0.141*
H24B	0.8524	0.1108	−0.1169	0.141*
H24C	0.8997	0.0726	−0.0111	0.141*
N1	0.59936 (17)	0.05326 (9)	0.32027 (12)	0.0467 (4)
N2	0.81105 (17)	0.13064 (10)	0.21658 (13)	0.0513 (4)
O1	0.40006 (15)	0.16132 (9)	0.09276 (10)	0.0569 (4)
O2	0.2849 (3)	0.04774 (14)	0.0780 (2)	0.1502 (12)
O3	0.74576 (14)	0.19711 (8)	0.01622 (10)	0.0536 (4)
O4	0.96565 (16)	0.24378 (10)	0.01729 (13)	0.0718 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0399 (11)	0.0407 (10)	0.0397 (9)	−0.0011 (8)	0.0016 (8)	−0.0007 (8)
C2	0.0485 (12)	0.0394 (11)	0.0519 (11)	0.0026 (9)	−0.0016 (9)	0.0003 (8)
C3	0.0670 (16)	0.0531 (13)	0.0834 (16)	0.0067 (11)	0.0054 (12)	0.0188 (12)
C4	0.0777 (19)	0.0577 (15)	0.0972 (19)	0.0184 (13)	−0.0026 (15)	0.0172 (13)
C5	0.0593 (16)	0.0675 (16)	0.108 (2)	0.0249 (13)	−0.0009 (14)	0.0111 (14)
C6	0.0494 (14)	0.0646 (15)	0.0979 (18)	0.0147 (11)	0.0098 (12)	0.0115 (13)
C7	0.0457 (12)	0.0445 (11)	0.0580 (12)	0.0051 (9)	0.0015 (9)	0.0023 (9)
C8	0.0384 (11)	0.0427 (11)	0.0477 (11)	0.0002 (8)	0.0036 (8)	0.0007 (8)
C9	0.0381 (11)	0.0445 (11)	0.0492 (11)	−0.0024 (8)	0.0060 (9)	0.0029 (8)
C10	0.0454 (13)	0.0746 (15)	0.0564 (12)	0.0038 (11)	0.0086 (10)	0.0019 (10)
C11	0.0522 (15)	0.0910 (18)	0.0725 (16)	0.0059 (13)	0.0183 (12)	−0.0046 (13)
C12	0.0405 (13)	0.0788 (17)	0.101 (2)	0.0113 (11)	0.0109 (13)	−0.0055 (14)
C13	0.0432 (13)	0.0661 (15)	0.0781 (16)	0.0040 (10)	−0.0068 (11)	0.0070 (11)
C14	0.0409 (12)	0.0490 (12)	0.0520 (11)	−0.0037 (9)	0.0017 (9)	0.0033 (9)
C15	0.0844 (18)	0.0636 (15)	0.0710 (16)	−0.0143 (14)	0.0131 (14)	−0.0085 (12)
C16	0.115 (2)	0.103 (2)	0.0653 (16)	−0.0082 (18)	0.0090 (16)	−0.0149 (15)
C17	0.0332 (10)	0.0432 (11)	0.0529 (11)	−0.0009 (8)	0.0005 (8)	0.0054 (8)
C18	0.0493 (13)	0.0485 (12)	0.0640 (13)	0.0034 (9)	0.0088 (10)	0.0036 (10)
C19	0.0546 (14)	0.0455 (13)	0.0865 (17)	0.0056 (10)	0.0044 (12)	0.0014 (11)
C20	0.0543 (14)	0.0490 (13)	0.0905 (17)	0.0007 (11)	−0.0080 (12)	0.0190 (12)
C21	0.0513 (13)	0.0609 (14)	0.0600 (13)	−0.0052 (10)	−0.0063 (10)	0.0185 (11)
C22	0.0328 (10)	0.0477 (11)	0.0531 (11)	−0.0055 (8)	−0.0048 (8)	0.0040 (9)
C23	0.0490 (13)	0.0624 (14)	0.0552 (12)	−0.0057 (11)	0.0080 (10)	0.0018 (10)
C24	0.0787 (19)	0.088 (2)	0.118 (2)	−0.0099 (15)	0.0290 (17)	−0.0343 (17)
N1	0.0458 (10)	0.0428 (9)	0.0517 (9)	−0.0007 (7)	0.0033 (7)	0.0048 (7)
N2	0.0399 (10)	0.0489 (10)	0.0656 (11)	0.0035 (7)	0.0075 (8)	0.0065 (8)
O1	0.0542 (9)	0.0661 (10)	0.0501 (8)	−0.0107 (7)	−0.0014 (7)	0.0030 (7)
O2	0.218 (3)	0.0990 (16)	0.142 (2)	−0.0865 (18)	0.092 (2)	−0.0508 (14)
O3	0.0461 (8)	0.0589 (9)	0.0562 (8)	−0.0123 (6)	0.0052 (6)	−0.0055 (6)
O4	0.0485 (10)	0.0730 (11)	0.0944 (12)	−0.0164 (8)	0.0085 (8)	−0.0079 (9)

C1—N1	1.319 (2)	C13—H13	0.9300
C1—C8	1.434 (2)	C14—O1	1.409 (2)
C1—C9	1.495 (3)	C15—O2	1.178 (3)
C2—N1	1.368 (2)	C15—O1	1.341 (3)
C2—C7	1.401 (3)	C15—C16	1.486 (3)
C2—C3	1.410 (3)	C16—H16A	0.9600
C3—C4	1.362 (3)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.393 (4)	C17—C22	1.388 (3)
C4—H4	0.9300	C17—C18	1.389 (3)
C5—C6	1.359 (3)	C18—C19	1.382 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.410 (3)	C19—C20	1.373 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—N2	1.367 (2)	C20—C21	1.379 (3)
C8—N2	1.319 (2)	C20—H20	0.9300
C8—C17	1.491 (3)	C21—C22	1.378 (3)
C9—C14	1.383 (3)	C21—H21	0.9300
C9—C10	1.395 (3)	C22—O3	1.403 (2)
C10—C11	1.378 (3)	C23—O4	1.188 (2)
C10—H10	0.9300	C23—O3	1.365 (2)
C11—C12	1.372 (4)	C23—C24	1.479 (3)
C11—H11	0.9300	C24—H24A	0.9600
C12—C13	1.376 (3)	C24—H24B	0.9600
C12—H12	0.9300	C24—H24C	0.9600
C13—C14	1.381 (3)
N1—C1—C8	121.58 (17)	C9—C14—O1	119.04 (17)
N1—C1—C9	115.76 (16)	O2—C15—O1	121.6 (2)
C8—C1—C9	122.60 (16)	O2—C15—C16	126.9 (3)
N1—C2—C7	121.18 (17)	O1—C15—C16	111.5 (2)
N1—C2—C3	119.48 (18)	C15—C16—H16A	109.5
C7—C2—C3	119.34 (19)	C15—C16—H16B	109.5
C4—C3—C2	119.8 (2)	H16A—C16—H16B	109.5
C4—C3—H3	120.1	C15—C16—H16C	109.5
C2—C3—H3	120.1	H16A—C16—H16C	109.5
C3—C4—C5	120.6 (2)	H16B—C16—H16C	109.5
C3—C4—H4	119.7	C22—C17—C18	117.67 (18)
C5—C4—H4	119.7	C22—C17—C8	121.31 (17)
C6—C5—C4	121.2 (2)	C18—C17—C8	120.91 (17)
C6—C5—H5	119.4	C19—C18—C17	121.1 (2)
C4—C5—H5	119.4	C19—C18—H18	119.4
C5—C6—C7	119.4 (2)	C17—C18—H18	119.4
C5—C6—H6	120.3	C20—C19—C18	119.8 (2)
C7—C6—H6	120.3	C20—C19—H19	120.1
N2—C7—C2	120.79 (17)	C18—C19—H19	120.1
N2—C7—C6	119.56 (19)	C19—C20—C21	120.3 (2)
C2—C7—C6	119.63 (19)	C19—C20—H20	119.8
N2—C8—C1	121.24 (17)	C21—C20—H20	119.8
N2—C8—C17	115.87 (16)	C22—C21—C20	119.4 (2)
C1—C8—C17	122.78 (16)	C22—C21—H21	120.3
C14—C9—C10	117.21 (18)	C20—C21—H21	120.3
C14—C9—C1	123.25 (17)	C21—C22—C17	121.62 (19)
C10—C9—C1	119.53 (17)	C21—C22—O3	120.24 (18)
C11—C10—C9	121.3 (2)	C17—C22—O3	118.01 (16)
C11—C10—H10	119.4	O4—C23—O3	123.0 (2)
C9—C10—H10	119.4	O4—C23—C24	126.2 (2)
C12—C11—C10	119.9 (2)	O3—C23—C24	110.8 (2)
C12—C11—H11	120.0	C23—C24—H24A	109.5
C10—C11—H11	120.0	C23—C24—H24B	109.5
C11—C12—C13	120.3 (2)	H24A—C24—H24B	109.5
C11—C12—H12	119.8	C23—C24—H24C	109.5
C13—C12—H12	119.8	H24A—C24—H24C	109.5
C12—C13—C14	119.2 (2)	H24B—C24—H24C	109.5
C12—C13—H13	120.4	C1—N1—C2	117.34 (16)
C14—C13—H13	120.4	C8—N2—C7	117.73 (16)
C13—C14—C9	122.07 (19)	C15—O1—C14	117.26 (16)
C13—C14—O1	118.89 (18)	C23—O3—C22	117.10 (15)
N1—C2—C3—C4	179.9 (2)	C1—C8—C17—C22	−131.55 (19)
C7—C2—C3—C4	−0.7 (3)	N2—C8—C17—C18	−124.0 (2)
C2—C3—C4—C5	−0.5 (4)	C1—C8—C17—C18	52.3 (3)
C3—C4—C5—C6	0.5 (4)	C22—C17—C18—C19	0.5 (3)
C4—C5—C6—C7	0.7 (4)	C8—C17—C18—C19	176.78 (19)
N1—C2—C7—N2	2.8 (3)	C17—C18—C19—C20	−0.2 (3)
C3—C2—C7—N2	−176.6 (2)	C18—C19—C20—C21	−0.4 (3)
N1—C2—C7—C6	−178.78 (19)	C19—C20—C21—C22	0.8 (3)
C3—C2—C7—C6	1.8 (3)	C20—C21—C22—C17	−0.5 (3)
C5—C6—C7—N2	176.6 (2)	C20—C21—C22—O3	175.29 (18)
C5—C6—C7—C2	−1.9 (4)	C18—C17—C22—C21	−0.1 (3)
N1—C1—C8—N2	3.9 (3)	C8—C17—C22—C21	−176.41 (18)
C9—C1—C8—N2	−178.99 (17)	C18—C17—C22—O3	−176.01 (17)
N1—C1—C8—C17	−172.21 (17)	C8—C17—C22—O3	7.7 (3)
C9—C1—C8—C17	4.9 (3)	C8—C1—N1—C2	−1.5 (3)
N1—C1—C9—C14	−124.4 (2)	C9—C1—N1—C2	−178.85 (16)
C8—C1—C9—C14	58.4 (3)	C7—C2—N1—C1	−1.7 (3)
N1—C1—C9—C10	54.9 (2)	C3—C2—N1—C1	177.72 (19)
C8—C1—C9—C10	−122.4 (2)	C1—C8—N2—C7	−2.7 (3)
C14—C9—C10—C11	−1.2 (3)	C17—C8—N2—C7	173.69 (17)
C1—C9—C10—C11	179.5 (2)	C2—C7—N2—C8	−0.5 (3)
C9—C10—C11—C12	0.3 (4)	C6—C7—N2—C8	−178.93 (19)
C10—C11—C12—C13	0.6 (4)	O2—C15—O1—C14	−4.3 (4)
C11—C12—C13—C14	−0.5 (4)	C16—C15—O1—C14	176.0 (2)
C12—C13—C14—C9	−0.5 (3)	C13—C14—O1—C15	−79.8 (3)
C12—C13—C14—O1	−179.3 (2)	C9—C14—O1—C15	101.3 (2)
C10—C9—C14—C13	1.3 (3)	O4—C23—O3—C22	−8.4 (3)
C1—C9—C14—C13	−179.44 (19)	C24—C23—O3—C22	171.6 (2)
C10—C9—C14—O1	−179.88 (17)	C21—C22—O3—C23	74.4 (2)
C1—C9—C14—O1	−0.6 (3)	C17—C22—O3—C23	−109.70 (19)
N2—C8—C17—C22	52.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O4i	0.93	2.43	3.329 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O4i	0.93	2.43	3.329 (2)	164

Symmetry code: (i) .