1,5-Dicyano-anthraquinone.

The complete mol-ecule of the title compound, C(16)H(6)N(2)O(2), which is generated by a crystallographic inversion centre, is almost planar (r.m.s. deviation = 0.04 Å). In the crystal, adjacent mol-ecules are stacked along the a axis, with a shortest centroid-centroid separation of 3.826 (2) Å.

Related literature

For the synthesis, see: Casey et al. (1999 ▶); Coulson (1930a ▶,b ▶). For some applications of anthraquinones, see: Alagesan & Samuelson (1997 ▶); Chang et al. (1996 ▶); Cheng et al. (1994 ▶); Kuritani et al. (1973 ▶); Lin et al. (1995 ▶).

Experimental

Crystal data

C16H6N2O2

M = 258.23

Monoclinic,

a = 3.8256 (10) Å

b = 7.0183 (19) Å

c = 21.249 (6) Å

β = 91.064 (4)°

V = 570.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.06 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer

4238 measured reflections

1013 independent reflections

600 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.149

S = 1.06

1013 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.18 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007993/hb5350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007993/hb5350Isup2.hkl

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

C16H6N2O2	F(000) = 264
Mr = 258.23	Dx = 1.503 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 614 reflections
a = 3.8256 (10) Å	θ = 3.1–25.4°
b = 7.0183 (19) Å	µ = 0.10 mm−1
c = 21.249 (6) Å	T = 293 K
β = 91.064 (4)°	Prism, yellow
V = 570.4 (3) Å3	0.35 × 0.06 × 0.03 mm
Z = 2

Bruker SMART APEX diffractometer	600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
graphite	θmax = 25.0°, θmin = 1.9°
ω scans	h = −4→4
4238 measured reflections	k = −8→8
1013 independent reflections	l = −25→25

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.1468P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
1013 reflections	Δρmax = 0.19 e Å−3
92 parameters	Δρmin = −0.18 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: 0.033 (9)

	x	y	z	Uiso*/Ueq
O1	0.8448 (7)	0.2052 (3)	0.55023 (10)	0.0691 (8)
N1	0.0797 (10)	0.7591 (5)	0.30574 (16)	0.0837 (11)
C1	0.6782 (8)	0.3375 (4)	0.52815 (13)	0.0407 (7)
C2	0.5829 (7)	0.3390 (4)	0.46013 (12)	0.0373 (7)
C3	0.6669 (8)	0.1823 (4)	0.42375 (14)	0.0473 (8)
H3	0.7752	0.0773	0.4423	0.057*
C4	0.5910 (9)	0.1815 (5)	0.36042 (15)	0.0583 (10)
H4	0.6438	0.0750	0.3364	0.070*
C5	0.4369 (9)	0.3378 (5)	0.33232 (15)	0.0566 (9)
H5	0.3903	0.3369	0.2892	0.068*
C6	0.3504 (7)	0.4968 (4)	0.36757 (13)	0.0430 (8)
C7	0.4220 (7)	0.4985 (4)	0.43270 (12)	0.0373 (7)
C8	0.1889 (8)	0.6593 (5)	0.33253 (14)	0.0424 (8)

	U11	U22	U33	U12	U13	U23
O1	0.097 (2)	0.0525 (15)	0.0572 (15)	0.0343 (13)	−0.0103 (13)	0.0056 (11)
N1	0.090 (3)	0.093 (3)	0.068 (2)	−0.006 (2)	0.0044 (19)	−0.0029 (19)
C1	0.0450 (18)	0.0323 (16)	0.0450 (17)	0.0043 (13)	0.0016 (13)	0.0035 (13)
C2	0.0383 (17)	0.0308 (16)	0.0427 (16)	0.0014 (12)	0.0011 (12)	0.0016 (12)
C3	0.053 (2)	0.0347 (18)	0.0540 (19)	0.0052 (13)	0.0015 (14)	−0.0067 (14)
C4	0.063 (2)	0.052 (2)	0.060 (2)	0.0047 (16)	0.0011 (17)	−0.0155 (17)
C5	0.058 (2)	0.070 (2)	0.0414 (17)	−0.0024 (17)	−0.0007 (15)	−0.0078 (16)
C6	0.0400 (17)	0.0455 (18)	0.0437 (17)	−0.0032 (14)	0.0028 (12)	−0.0009 (14)
C7	0.0325 (15)	0.0377 (17)	0.0416 (16)	−0.0027 (12)	0.0024 (11)	0.0024 (12)
C8	0.0388 (18)	0.050 (2)	0.0382 (17)	0.0024 (14)	−0.0053 (13)	0.0059 (15)

O1—C1	1.216 (3)	C4—C5	1.376 (4)
N1—C8	0.991 (4)	C4—H4	0.9300
C1—C7i	1.475 (4)	C5—C6	1.387 (4)
C1—C2	1.484 (4)	C5—H5	0.9300
C2—C3	1.386 (4)	C6—C7	1.406 (3)
C2—C7	1.399 (4)	C6—C8	1.490 (4)
C3—C4	1.371 (4)	C7—C1i	1.475 (4)
C3—H3	0.9300
O1—C1—C7i	121.2 (3)	C5—C4—H4	119.9
O1—C1—C2	119.9 (3)	C4—C5—C6	120.8 (3)
C7i—C1—C2	118.8 (2)	C4—C5—H5	119.6
C3—C2—C7	120.5 (3)	C6—C5—H5	119.6
C3—C2—C1	118.8 (2)	C5—C6—C7	119.6 (3)
C7—C2—C1	120.7 (2)	C5—C6—C8	116.5 (3)
C4—C3—C2	120.2 (3)	C7—C6—C8	123.9 (3)
C4—C3—H3	119.9	C2—C7—C6	118.7 (3)
C2—C3—H3	119.9	C2—C7—C1i	120.4 (2)
C3—C4—C5	120.2 (3)	C6—C7—C1i	120.9 (3)
C3—C4—H4	119.9	N1—C8—C6	174.6 (4)
O1—C1—C2—C3	4.2 (4)	C4—C5—C6—C8	179.3 (3)
C7i—C1—C2—C3	−177.9 (3)	C3—C2—C7—C6	−0.5 (4)
O1—C1—C2—C7	−173.6 (3)	C1—C2—C7—C6	177.2 (2)
C7i—C1—C2—C7	4.3 (4)	C3—C2—C7—C1i	177.9 (3)
C7—C2—C3—C4	−0.4 (4)	C1—C2—C7—C1i	−4.4 (4)
C1—C2—C3—C4	−178.2 (3)	C5—C6—C7—C2	0.6 (4)
C2—C3—C4—C5	1.3 (5)	C8—C6—C7—C2	−178.4 (3)
C3—C4—C5—C6	−1.2 (5)	C5—C6—C7—C1i	−177.8 (3)
C4—C5—C6—C7	0.2 (4)	C8—C6—C7—C1i	3.2 (4)