8,15-Dioxa-10,13-di-aza-tetra-cyclo-[14.4.0.0(2,7).0(9,14)]icosa-1(16),2,4,6,9(14),10,12,17,19-nona-ene.

The asymmetric unit of the title compound, C16H10N2O2, contains one half-mol-ecule, the complete mol-ecule being generated by twofold rotation symmetry. The plane of the pyrazine ring forms a dihedral angle of 64.87 (6)° with that of the benzene ring, and the planes of the two benzene rings are inclined to one another by 54.20 (6)°. The O atom deviates from the plane of the benzene ring by 0.1549 (8) Å. There are no significant inter-molecular inter-actions in the crystal.

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009 ▶); Dubinina et al. (2006 ▶); Ellsworth et al. (2007 ▶); Mukaiyama et al. (2007 ▶). For background to the fluorescence properties of related compounds, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶) and for their biological activity, see: Seitz et al. (2002 ▶); Temple et al. (1970 ▶). For a related structure, see: Nasir et al. (2010 ▶).

Experimental

Crystal data

C16H10N2O2

M = 262.26

Orthorhombic,

a = 14.429 (3) Å

b = 10.162 (2) Å

c = 8.3313 (18) Å

V = 1221.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.972, T max = 0.981

6082 measured reflections

1502 independent reflections

1226 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.106

S = 1.03

1502 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011318/su2586sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011318/su2586Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011318/su2586Isup3.cml

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

C16H10N2O2	F(000) = 544
Mr = 262.26	Dx = 1.426 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1502 reflections
a = 14.429 (3) Å	θ = 2.5–28.3°
b = 10.162 (2) Å	µ = 0.10 mm−1
c = 8.3313 (18) Å	T = 293 K
V = 1221.6 (4) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker SMART APEXII area-detector diffractometer	1502 independent reflections
Radiation source: fine-focus sealed tube	1226 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→19
Tmin = 0.972, Tmax = 0.981	k = −5→13
6082 measured reflections	l = −7→10

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1721P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1502 reflections	Δρmax = 0.22 e Å−3
92 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (3)

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 > 2sigma(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	0.53624 (10)	1.14890 (12)	0.19682 (18)	0.0623 (4)
H1	0.5600	1.2289	0.1616	0.075*
C2	0.53746 (8)	0.92738 (11)	0.19677 (13)	0.0426 (3)
C3	0.60493 (7)	0.71770 (11)	0.24296 (13)	0.0395 (3)
C4	0.54878 (7)	0.61036 (10)	0.27797 (12)	0.0390 (3)
C5	0.58736 (8)	0.50933 (12)	0.36919 (14)	0.0480 (3)
H5	0.5523	0.4349	0.3922	0.058*
C6	0.67748 (9)	0.51846 (14)	0.42609 (16)	0.0568 (4)
H6	0.7020	0.4509	0.4883	0.068*
C7	0.73073 (8)	0.62674 (15)	0.39094 (15)	0.0594 (4)
H7	0.7908	0.6328	0.4305	0.071*
C8	0.69529 (8)	0.72654 (12)	0.29713 (15)	0.0505 (3)
H8	0.7317	0.7989	0.2706	0.061*
N1	0.57395 (7)	1.03683 (10)	0.14200 (14)	0.0546 (3)
O1	0.57275 (5)	0.81298 (8)	0.13462 (9)	0.0446 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0751 (9)	0.0430 (6)	0.0688 (9)	−0.0077 (6)	−0.0246 (6)	0.0065 (6)
C2	0.0464 (6)	0.0431 (6)	0.0383 (6)	−0.0018 (4)	−0.0088 (4)	0.0017 (4)
C3	0.0383 (5)	0.0458 (5)	0.0344 (5)	0.0021 (4)	0.0021 (4)	−0.0019 (4)
C4	0.0382 (5)	0.0429 (5)	0.0357 (5)	0.0033 (4)	0.0052 (4)	−0.0026 (4)
C5	0.0498 (6)	0.0476 (6)	0.0467 (6)	0.0092 (5)	0.0103 (5)	0.0029 (5)
C6	0.0547 (7)	0.0697 (8)	0.0461 (6)	0.0241 (6)	0.0024 (5)	0.0049 (6)
C7	0.0417 (6)	0.0870 (10)	0.0496 (7)	0.0130 (6)	−0.0066 (5)	−0.0073 (7)
C8	0.0394 (6)	0.0623 (7)	0.0497 (7)	−0.0040 (5)	−0.0005 (5)	−0.0078 (6)
N1	0.0593 (6)	0.0495 (6)	0.0548 (6)	−0.0094 (5)	−0.0118 (5)	0.0090 (5)
O1	0.0486 (5)	0.0467 (4)	0.0384 (4)	−0.0009 (3)	0.0040 (3)	0.0041 (3)

C1—N1	1.3423 (17)	C4—C5	1.3935 (16)
C1—C1i	1.371 (3)	C4—C4i	1.483 (2)
C1—H1	0.9300	C5—C6	1.3871 (17)
C2—N1	1.3124 (15)	C5—H5	0.9300
C2—O1	1.3707 (14)	C6—C7	1.374 (2)
C2—C2i	1.398 (2)	C6—H6	0.9300
C3—C8	1.3826 (15)	C7—C8	1.3787 (18)
C3—C4	1.3897 (15)	C7—H7	0.9300
C3—O1	1.4029 (13)	C8—H8	0.9300
N1—C1—C1i	121.95 (8)	C6—C5—H5	119.6
N1—C1—H1	119.0	C4—C5—H5	119.6
C1i—C1—H1	119.0	C7—C6—C5	120.33 (12)
N1—C2—O1	116.01 (10)	C7—C6—H6	119.8
N1—C2—C2i	122.05 (7)	C5—C6—H6	119.8
O1—C2—C2i	121.79 (6)	C6—C7—C8	120.18 (11)
C8—C3—C4	122.16 (11)	C6—C7—H7	119.9
C8—C3—O1	118.51 (10)	C8—C7—H7	119.9
C4—C3—O1	118.93 (9)	C7—C8—C3	119.14 (11)
C3—C4—C5	117.38 (10)	C7—C8—H8	120.4
C3—C4—C4i	119.18 (8)	C3—C8—H8	120.4
C5—C4—C4i	123.41 (8)	C2—N1—C1	115.99 (12)
C6—C5—C4	120.77 (12)	C2—O1—C3	117.73 (8)
C8—C3—C4—C5	−0.82 (16)	C4—C3—C8—C7	−0.97 (17)
O1—C3—C4—C5	171.84 (9)	O1—C3—C8—C7	−173.66 (10)
C8—C3—C4—C4i	177.25 (11)	O1—C2—N1—C1	176.77 (10)
O1—C3—C4—C4i	−10.09 (16)	C2i—C2—N1—C1	1.3 (2)
C3—C4—C5—C6	1.84 (16)	C1i—C1—N1—C2	−0.2 (2)
C4i—C4—C5—C6	−176.15 (12)	N1—C2—O1—C3	126.38 (10)
C4—C5—C6—C7	−1.07 (18)	C2i—C2—O1—C3	−58.13 (16)
C5—C6—C7—C8	−0.78 (19)	C8—C3—O1—C2	−86.29 (12)
C6—C7—C8—C3	1.78 (18)	C4—C3—O1—C2	100.77 (11)