rac-1,2,3,4-Tetra-hydro-1,4-methano-anthracene-6,7-dicarbonitrile.

The title compound, C(17)H(12)N(2), comprises a norbornane unit having a dicyanona-phthalene ring fused on one side. Both cyano groups are twisted slightly out of the plane of the naphthalene ring system [C-C-C-C torsion angle = 1.9 (2)°]. In the crystal, inversion-related mol-ecules are linked by pairs of weak C-H⋯N hydrogen bonds, forming dimers.

Related literature

For the spectroscopy of the title compound and its prepartion, see: Chen et al. (2006 ▶). For the spectroscopy and electronic device applications of rigid oligo-norbornyl compounds, see: Chen et al. (2002 ▶); Chow et al. (2005 ▶); Foitzik et al. (2009 ▶); Jansen et al. (2010 ▶); Tang et al. (2009 ▶). For related structures, see: Çelik et al. (2006 ▶); Chen et al. (2011 ▶); Lough et al. (2006 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H12N2

M = 244.29

Triclinic,

a = 6.1019 (4) Å

b = 10.7078 (6) Å

c = 11.3928 (7) Å

α = 65.173 (5)°

β = 84.768 (5)°

γ = 73.900 (5)°

V = 648.82 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 297 K

0.64 × 0.52 × 0.48 mm

Data collection

Bruker SMART 1000 CCD detector diffractometer

5692 measured reflections

2997 independent reflections

1707 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.102

S = 1.00

2997 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047611/xu5368sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047611/xu5368Isup2.hkl

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

C17H12N2	Z = 2
Mr = 244.29	F(000) = 256
Triclinic, P1	Dx = 1.250 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1019 (4) Å	Cell parameters from 2453 reflections
b = 10.7078 (6) Å	θ = 3.5–29.1°
c = 11.3928 (7) Å	µ = 0.08 mm−1
α = 65.173 (5)°	T = 297 K
β = 84.768 (5)°	Parallelepiped, colorless
γ = 73.900 (5)°	0.64 × 0.52 × 0.48 mm
V = 648.82 (7) Å3

Bruker SMART 1000 CCD detector diffractometer	1707 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 29.2°, θmin = 3.5°
ω scans	h = −8→8
5692 measured reflections	k = −14→14
2997 independent reflections	l = −14→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3
2997 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.12 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
N1	0.2097 (3)	0.55552 (16)	0.34283 (14)	0.1097 (6)
N2	−0.1343 (2)	0.29042 (13)	0.33818 (12)	0.0842 (4)
C1	0.78769 (19)	−0.08604 (13)	0.86297 (11)	0.0499 (3)
C2	0.74313 (19)	0.04981 (12)	0.77112 (11)	0.0502 (3)
H2A	0.8289	0.1101	0.7692	0.060*
C3	0.56549 (19)	0.09894 (12)	0.67840 (11)	0.0455 (3)
C4	0.5038 (2)	0.24135 (12)	0.58626 (11)	0.0538 (3)
H4A	0.5862	0.3034	0.5841	0.065*
C5	0.3264 (2)	0.29073 (13)	0.50013 (11)	0.0534 (3)
C6	0.2009 (2)	0.19691 (13)	0.50028 (11)	0.0502 (3)
C7	0.2591 (2)	0.05771 (13)	0.58871 (11)	0.0516 (3)
H7A	0.1780	−0.0038	0.5879	0.062*
C8	0.43752 (19)	0.00511 (12)	0.68053 (10)	0.0459 (3)
C9	0.4902 (2)	−0.13666 (12)	0.77692 (11)	0.0537 (3)
H9A	0.4095	−0.1996	0.7790	0.064*
C10	0.6589 (2)	−0.17993 (12)	0.86607 (11)	0.0521 (3)
C11	0.7439 (2)	−0.31536 (13)	0.98405 (12)	0.0652 (4)
H11A	0.7136	−0.4008	0.9845	0.078*
C12	0.6585 (2)	−0.28095 (14)	1.10178 (12)	0.0680 (4)
H12A	0.4960	−0.2353	1.0934	0.082*
H12B	0.6900	−0.3666	1.1818	0.082*
C13	0.7968 (2)	−0.17846 (14)	1.09723 (12)	0.0628 (4)
H13A	0.8894	−0.2172	1.1757	0.075*
H13B	0.6968	−0.0861	1.0861	0.075*
C14	0.9474 (2)	−0.16675 (13)	0.97878 (12)	0.0596 (3)
H14A	1.0812	−0.1317	0.9752	0.071*
C15	0.9970 (3)	−0.31873 (14)	0.98683 (14)	0.0739 (4)
H15A	1.0779	−0.3294	0.9128	0.089*
H15B	1.0768	−0.3906	1.0666	0.089*
C16	0.2613 (2)	0.43837 (17)	0.41097 (14)	0.0729 (4)
C17	0.0154 (2)	0.24891 (14)	0.40941 (13)	0.0598 (3)

	U11	U22	U33	U12	U13	U23
N1	0.1226 (13)	0.0715 (9)	0.1080 (11)	−0.0383 (8)	−0.0460 (10)	0.0062 (8)
N2	0.0804 (9)	0.1061 (10)	0.0719 (8)	−0.0326 (8)	−0.0084 (7)	−0.0352 (8)
C1	0.0473 (7)	0.0524 (7)	0.0519 (7)	−0.0076 (6)	0.0070 (6)	−0.0279 (6)
C2	0.0455 (7)	0.0567 (8)	0.0545 (7)	−0.0178 (6)	0.0066 (6)	−0.0271 (6)
C3	0.0461 (7)	0.0493 (7)	0.0457 (7)	−0.0166 (5)	0.0097 (5)	−0.0232 (6)
C4	0.0584 (8)	0.0549 (8)	0.0534 (7)	−0.0280 (6)	0.0069 (6)	−0.0202 (6)
C5	0.0573 (8)	0.0543 (8)	0.0482 (7)	−0.0205 (6)	0.0036 (6)	−0.0174 (6)
C6	0.0545 (7)	0.0589 (8)	0.0437 (7)	−0.0201 (6)	0.0072 (5)	−0.0250 (6)
C7	0.0593 (8)	0.0613 (8)	0.0492 (7)	−0.0277 (6)	0.0091 (6)	−0.0313 (7)
C8	0.0522 (7)	0.0497 (7)	0.0446 (7)	−0.0177 (5)	0.0104 (6)	−0.0270 (6)
C9	0.0672 (9)	0.0491 (7)	0.0563 (8)	−0.0232 (6)	0.0096 (7)	−0.0292 (6)
C10	0.0610 (8)	0.0454 (7)	0.0526 (7)	−0.0091 (6)	0.0064 (6)	−0.0267 (6)
C11	0.0831 (11)	0.0438 (7)	0.0639 (9)	−0.0080 (6)	−0.0018 (7)	−0.0222 (6)
C12	0.0800 (10)	0.0589 (8)	0.0550 (8)	−0.0135 (7)	0.0037 (7)	−0.0173 (7)
C13	0.0669 (9)	0.0625 (8)	0.0546 (8)	−0.0064 (7)	−0.0032 (6)	−0.0256 (7)
C14	0.0512 (8)	0.0602 (8)	0.0626 (8)	−0.0024 (6)	−0.0016 (6)	−0.0280 (7)
C15	0.0777 (11)	0.0603 (9)	0.0685 (9)	0.0089 (7)	−0.0018 (7)	−0.0284 (7)
C16	0.0760 (11)	0.0660 (10)	0.0707 (10)	−0.0296 (8)	−0.0158 (8)	−0.0122 (8)
C17	0.0626 (8)	0.0724 (9)	0.0521 (8)	−0.0266 (7)	0.0038 (6)	−0.0279 (7)

N1—C16	1.1327 (16)	C8—C9	1.4169 (15)
N2—C17	1.1390 (14)	C9—C10	1.3557 (15)
C1—C2	1.3562 (15)	C9—H9A	0.9300
C1—C10	1.4256 (16)	C10—C11	1.5006 (16)
C1—C14	1.4990 (16)	C11—C15	1.5380 (19)
C2—C3	1.4119 (15)	C11—C12	1.5450 (17)
C2—H2A	0.9300	C11—H11A	0.9800
C3—C4	1.4065 (15)	C12—C13	1.5414 (19)
C3—C8	1.4252 (15)	C12—H12A	0.9700
C4—C5	1.3616 (16)	C12—H12B	0.9700
C4—H4A	0.9300	C13—C14	1.5419 (18)
C5—C6	1.4213 (16)	C13—H13A	0.9700
C5—C16	1.4373 (19)	C13—H13B	0.9700
C6—C7	1.3687 (16)	C14—C15	1.5346 (18)
C6—C17	1.4296 (18)	C14—H14A	0.9800
C7—C8	1.4035 (15)	C15—H15A	0.9700
C7—H7A	0.9300	C15—H15B	0.9700
C2—C1—C10	120.79 (10)	C10—C11—C12	106.33 (9)
C2—C1—C14	132.93 (11)	C15—C11—C12	100.68 (11)
C10—C1—C14	106.15 (11)	C10—C11—H11A	115.7
C1—C2—C3	119.46 (11)	C15—C11—H11A	115.7
C1—C2—H2A	120.3	C12—C11—H11A	115.7
C3—C2—H2A	120.3	C13—C12—C11	103.09 (11)
C2—C3—C4	121.51 (10)	C13—C12—H12A	111.1
C2—C3—C8	119.94 (11)	C11—C12—H12A	111.1
C4—C3—C8	118.49 (10)	C13—C12—H12B	111.1
C5—C4—C3	121.73 (11)	C11—C12—H12B	111.1
C5—C4—H4A	119.1	H12A—C12—H12B	109.1
C3—C4—H4A	119.1	C12—C13—C14	103.60 (10)
C4—C5—C6	119.99 (11)	C12—C13—H13A	111.0
C4—C5—C16	120.35 (11)	C14—C13—H13A	111.0
C6—C5—C16	119.63 (11)	C12—C13—H13B	111.0
C7—C6—C17	120.93 (11)	C14—C13—H13B	111.0
C7—C6—C5	119.19 (10)	H13A—C13—H13B	109.0
C17—C6—C5	119.87 (11)	C1—C14—C13	105.82 (10)
C6—C7—C8	121.89 (10)	C1—C14—C15	100.52 (10)
C6—C7—H7A	119.1	C13—C14—C15	100.81 (11)
C8—C7—H7A	119.1	C1—C14—H14A	115.8
C7—C8—C9	122.15 (10)	C13—C14—H14A	115.8
C7—C8—C3	118.67 (10)	C15—C14—H14A	115.8
C9—C8—C3	119.17 (10)	C11—C15—C14	94.37 (10)
C10—C9—C8	119.52 (11)	C11—C15—H15A	112.9
C10—C9—H9A	120.2	C14—C15—H15A	112.9
C8—C9—H9A	120.2	C11—C15—H15B	112.9
C9—C10—C1	121.11 (11)	C14—C15—H15B	112.9
C9—C10—C11	132.89 (12)	H15A—C15—H15B	110.3
C1—C10—C11	105.90 (10)	N1—C16—C5	178.55 (15)
C10—C11—C15	100.49 (11)	N2—C17—C6	179.15 (14)
C10—C1—C2—C3	0.63 (16)	C8—C9—C10—C11	174.59 (11)
C14—C1—C2—C3	−174.57 (11)	C2—C1—C10—C9	0.59 (17)
C1—C2—C3—C4	176.05 (10)	C14—C1—C10—C9	176.93 (10)
C1—C2—C3—C8	−1.11 (16)	C2—C1—C10—C11	−176.27 (10)
C2—C3—C4—C5	−177.21 (11)	C14—C1—C10—C11	0.07 (12)
C8—C3—C4—C5	0.00 (16)	C9—C10—C11—C15	149.70 (13)
C3—C4—C5—C6	−1.17 (18)	C1—C10—C11—C15	−33.97 (12)
C3—C4—C5—C16	177.24 (11)	C9—C10—C11—C12	−105.79 (15)
C4—C5—C6—C7	0.78 (17)	C1—C10—C11—C12	70.54 (13)
C16—C5—C6—C7	−177.64 (11)	C10—C11—C12—C13	−68.26 (13)
C4—C5—C6—C17	−179.75 (11)	C15—C11—C12—C13	36.12 (12)
C16—C5—C6—C17	1.83 (18)	C11—C12—C13—C14	−0.59 (12)
C17—C6—C7—C8	−178.66 (11)	C2—C1—C14—C13	105.11 (14)
C5—C6—C7—C8	0.80 (17)	C10—C1—C14—C13	−70.59 (11)
C6—C7—C8—C9	176.37 (10)	C2—C1—C14—C15	−150.36 (13)
C6—C7—C8—C3	−1.95 (16)	C10—C1—C14—C15	33.94 (13)
C2—C3—C8—C7	178.78 (10)	C12—C13—C14—C1	69.09 (12)
C4—C3—C8—C7	1.53 (15)	C12—C13—C14—C15	−35.23 (12)
C2—C3—C8—C9	0.42 (15)	C10—C11—C15—C14	52.20 (11)
C4—C3—C8—C9	−176.84 (10)	C12—C11—C15—C14	−56.81 (11)
C7—C8—C9—C10	−177.53 (11)	C1—C14—C15—C11	−52.13 (12)
C3—C8—C9—C10	0.78 (16)	C13—C14—C15—C11	56.39 (11)
C8—C9—C10—C1	−1.29 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···N1i	0.93	2.61	3.505 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯N1i	0.93	2.61	3.505 (2)	162

Symmetry code: (i) .