Penta-cyclo-[8.2.1.1(4,7).0(2,9).0(3,8)]tetra-deca-5,11-diene.

The title compound, C(14)H(16), was prepared through [2 + 2] cyclo-addition of norbornadiene. There are two independent mol-ecules in the asymmetric unit: each is centrosymmetric with the centroid of the four-membered ring located about an inversion center. Each mol-ecule possesses an exo-trans-exo conformation.

Related literature

For the preparation of the title compound, see: Chen et al. (2002 ▶). For the spectroscopy of D–S–A mol­ecules (electron donor–acceptor chromophores linked by spacers), see: Chen et al. (2002 ▶, 2006 ▶); Chow et al. (1999 ▶, 2005 ▶). For the electronic device applications of D–S–A mol­ecules, see: Huang et al. (2011 ▶); Lee et al. (2011 ▶); Lin et al. (2010 ▶); Raposo et al. (2011 ▶); Wang et al. (2011 ▶); Wu et al. (2010 ▶); Xiang et al. (2011 ▶); Zhou et al. (2011 ▶). For related structures, see: Chen et al. (2011a ▶,b ▶); Tsai et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H16

M = 184.27

Monoclinic,

a = 10.7893 (7) Å

b = 10.8730 (6) Å

c = 9.2407 (6) Å

β = 109.022 (7)°

V = 1024.85 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 297 K

0.70 × 0.60 × 0.50 mm

Data collection

Bruker SMART CCD area-detector diffractometer

4696 measured reflections

2375 independent reflections

1662 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.157

S = 1.07

2375 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536812038780/xu5620sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038780/xu5620Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038780/xu5620Isup3.cml

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

C14H16	F(000) = 400
Mr = 184.27	Dx = 1.194 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2538 reflections
a = 10.7893 (7) Å	θ = 3.0–29.2°
b = 10.8730 (6) Å	µ = 0.07 mm−1
c = 9.2407 (6) Å	T = 297 K
β = 109.022 (7)°	Parallelepiped, colorless
V = 1024.85 (11) Å3	0.70 × 0.60 × 0.50 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1662 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 29.2°, θmin = 3.0°
ω scans	h = −13→14
4696 measured reflections	k = −13→14
2375 independent reflections	l = −12→10

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.098P)2 + 0.0079P] where P = (Fo2 + 2Fc2)/3
2375 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.20 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
C1	0.48726 (13)	0.60019 (11)	−0.00625 (14)	0.0354 (3)
H1A	0.4862	0.6542	0.0783	0.042*
C2	0.60674 (12)	0.51050 (12)	0.03238 (15)	0.0363 (3)
H2A	0.6678	0.5178	0.1370	0.044*
C3	0.66729 (14)	0.54040 (14)	−0.09413 (18)	0.0493 (4)
H3A	0.7283	0.4794	−0.1102	0.059*
C4	0.71928 (16)	0.66991 (16)	−0.05935 (19)	0.0626 (5)
H4A	0.8071	0.6926	−0.0217	0.075*
C5	0.61875 (17)	0.74451 (15)	−0.09167 (18)	0.0576 (5)
H5A	0.6226	0.8296	−0.0805	0.069*
C6	0.49605 (14)	0.66859 (12)	−0.15005 (16)	0.0414 (4)
H6A	0.4169	0.7122	−0.2113	0.050*
C7	0.54463 (14)	0.56681 (14)	−0.23163 (15)	0.0455 (4)
H7A	0.4851	0.4973	−0.2591	0.055*
H7B	0.5651	0.5961	−0.3204	0.055*
C8	0.89681 (12)	0.98409 (12)	−0.01155 (15)	0.0366 (3)
H8A	0.8246	0.9749	−0.1082	0.044*
C9	0.98405 (13)	1.09971 (11)	−0.00363 (15)	0.0377 (3)
H9A	0.9572	1.1510	−0.0959	0.045*
C10	0.97907 (14)	1.16558 (13)	0.14375 (18)	0.0485 (4)
H10A	1.0466	1.2278	0.1875	0.058*
C11	0.83794 (17)	1.20757 (15)	0.1034 (2)	0.0606 (5)
H11A	0.8086	1.2884	0.0865	0.073*
C12	0.76413 (15)	1.11028 (15)	0.09629 (19)	0.0572 (5)
H12A	0.6736	1.1098	0.0736	0.069*
C13	0.85276 (13)	0.99966 (13)	0.13162 (17)	0.0436 (4)
H13A	0.8180	0.9259	0.1658	0.052*
C14	0.97517 (14)	1.05643 (14)	0.24666 (16)	0.0477 (4)
H14A	1.0517	1.0039	0.2680	0.057*
H14B	0.9617	1.0811	0.3413	0.057*

	U11	U22	U33	U12	U13	U23
C1	0.0424 (7)	0.0336 (7)	0.0330 (7)	0.0020 (5)	0.0163 (6)	0.0007 (5)
C2	0.0315 (7)	0.0444 (8)	0.0324 (6)	0.0012 (5)	0.0095 (5)	0.0066 (5)
C3	0.0415 (8)	0.0599 (9)	0.0551 (9)	0.0096 (7)	0.0276 (7)	0.0171 (8)
C4	0.0453 (9)	0.0788 (12)	0.0611 (10)	−0.0188 (8)	0.0140 (8)	0.0218 (9)
C5	0.0699 (12)	0.0488 (9)	0.0535 (9)	−0.0171 (8)	0.0190 (8)	0.0093 (7)
C6	0.0450 (8)	0.0404 (7)	0.0397 (7)	0.0059 (6)	0.0151 (6)	0.0111 (6)
C7	0.0552 (9)	0.0520 (8)	0.0348 (7)	0.0004 (7)	0.0223 (7)	0.0053 (6)
C8	0.0320 (7)	0.0425 (7)	0.0348 (7)	−0.0061 (5)	0.0103 (5)	−0.0051 (5)
C9	0.0418 (8)	0.0336 (7)	0.0389 (7)	−0.0026 (5)	0.0150 (6)	0.0015 (5)
C10	0.0528 (9)	0.0404 (8)	0.0573 (9)	−0.0115 (6)	0.0249 (7)	−0.0150 (7)
C11	0.0694 (12)	0.0495 (9)	0.0710 (11)	0.0158 (8)	0.0340 (9)	−0.0025 (8)
C12	0.0446 (9)	0.0711 (12)	0.0600 (10)	0.0089 (8)	0.0228 (8)	−0.0068 (8)
C13	0.0410 (8)	0.0490 (8)	0.0464 (8)	−0.0058 (6)	0.0217 (7)	−0.0023 (6)
C14	0.0481 (9)	0.0603 (9)	0.0363 (7)	−0.0013 (7)	0.0159 (6)	−0.0069 (7)

C1—C6	1.5525 (16)	C8—C9ii	1.5443 (17)
C1—C2i	1.5413 (17)	C8—C13	1.5539 (18)
C1—C2	1.5621 (17)	C8—C9	1.5578 (17)
C1—H1A	0.9800	C8—H8A	0.9800
C2—C1i	1.5413 (17)	C9—C10	1.5551 (18)
C2—C3	1.5483 (17)	C9—C8ii	1.5442 (17)
C2—H2A	0.9800	C9—H9A	0.9800
C3—C4	1.511 (2)	C10—C11	1.515 (2)
C3—C7	1.534 (2)	C10—C14	1.530 (2)
C3—H3A	0.9800	C10—H10A	0.9800
C4—C5	1.309 (2)	C11—C12	1.313 (2)
C4—H4A	0.9300	C11—H11A	0.9300
C5—C6	1.503 (2)	C12—C13	1.505 (2)
C5—H5A	0.9300	C12—H12A	0.9300
C6—C7	1.5249 (19)	C13—C14	1.5298 (19)
C6—H6A	0.9800	C13—H13A	0.9800
C7—H7A	0.9700	C14—H14A	0.9700
C7—H7B	0.9700	C14—H14B	0.9700
C6—C1—C2i	117.43 (11)	C9ii—C8—C13	117.61 (11)
C6—C1—C2	102.62 (9)	C9ii—C8—C9	89.98 (9)
C2i—C1—C2	90.01 (9)	C13—C8—C9	102.70 (10)
C6—C1—H1A	114.5	C9ii—C8—H8A	114.4
C2i—C1—H1A	114.5	C13—C8—H8A	114.4
C2—C1—H1A	114.5	C9—C8—H8A	114.4
C1i—C2—C3	117.63 (11)	C10—C9—C8ii	117.23 (12)
C1i—C2—C1	89.99 (9)	C10—C9—C8	102.70 (9)
C3—C2—C1	102.49 (10)	C8ii—C9—C8	90.02 (9)
C1i—C2—H2A	114.5	C10—C9—H9A	114.6
C3—C2—H2A	114.5	C8ii—C9—H9A	114.6
C1—C2—H2A	114.5	C8—C9—H9A	114.6
C4—C3—C7	99.32 (12)	C11—C10—C9	104.01 (12)
C4—C3—C2	104.70 (12)	C11—C10—C14	99.07 (12)
C7—C3—C2	101.67 (10)	C9—C10—C14	101.71 (10)
C4—C3—H3A	116.2	C11—C10—H10A	116.5
C7—C3—H3A	116.2	C9—C10—H10A	116.5
C2—C3—H3A	116.2	C14—C10—H10A	116.5
C5—C4—C3	107.85 (14)	C12—C11—C10	108.30 (14)
C5—C4—H4A	126.1	C12—C11—H11A	125.8
C3—C4—H4A	126.1	C10—C11—H11A	125.8
C4—C5—C6	108.00 (14)	C11—C12—C13	107.52 (13)
C4—C5—H5A	126.0	C11—C12—H12A	126.2
C6—C5—H5A	126.0	C13—C12—H12A	126.2
C5—C6—C7	99.87 (11)	C12—C13—C14	99.90 (12)
C5—C6—C1	104.38 (11)	C12—C13—C8	104.56 (11)
C7—C6—C1	101.67 (10)	C14—C13—C8	101.61 (9)
C5—C6—H6A	116.2	C12—C13—H13A	116.1
C7—C6—H6A	116.2	C14—C13—H13A	116.1
C1—C6—H6A	116.2	C8—C13—H13A	116.1
C3—C7—C6	93.97 (11)	C13—C14—C10	94.21 (11)
C3—C7—H7A	112.9	C13—C14—H14A	112.9
C6—C7—H7A	112.9	C10—C14—H14A	112.9
C3—C7—H7B	112.9	C13—C14—H14B	112.9
C6—C7—H7B	112.9	C10—C14—H14B	112.9
H7A—C7—H7B	110.3	H14A—C14—H14B	110.3
C6—C1—C2—C1i	−118.17 (11)	C9ii—C8—C9—C10	−117.97 (12)
C2i—C1—C2—C1i	0.0	C13—C8—C9—C10	0.39 (13)
C6—C1—C2—C3	0.19 (13)	C9ii—C8—C9—C8ii	0.0
C2i—C1—C2—C3	118.36 (12)	C13—C8—C9—C8ii	118.36 (12)
C1i—C2—C3—C4	163.80 (12)	C8ii—C9—C10—C11	−164.01 (12)
C1—C2—C3—C4	67.16 (13)	C8—C9—C10—C11	−67.32 (13)
C1i—C2—C3—C7	60.79 (15)	C8ii—C9—C10—C14	−61.43 (13)
C1—C2—C3—C7	−35.86 (14)	C8—C9—C10—C14	35.25 (13)
C7—C3—C4—C5	33.64 (15)	C9—C10—C11—C12	71.17 (16)
C2—C3—C4—C5	−71.14 (15)	C14—C10—C11—C12	−33.41 (16)
C3—C4—C5—C6	−0.36 (17)	C10—C11—C12—C13	0.03 (18)
C4—C5—C6—C7	−33.32 (15)	C11—C12—C13—C14	33.45 (15)
C4—C5—C6—C1	71.54 (14)	C11—C12—C13—C8	−71.41 (15)
C2i—C1—C6—C5	−164.42 (11)	C9ii—C8—C13—C12	164.42 (11)
C2—C1—C6—C5	−67.74 (12)	C9—C8—C13—C12	67.68 (13)
C2i—C1—C6—C7	−60.91 (14)	C9ii—C8—C13—C14	60.85 (14)
C2—C1—C6—C7	35.78 (12)	C9—C8—C13—C14	−35.90 (13)
C4—C3—C7—C6	−50.28 (11)	C12—C13—C14—C10	−50.63 (11)
C2—C3—C7—C6	56.97 (12)	C8—C13—C14—C10	56.62 (12)
C5—C6—C7—C3	50.32 (11)	C11—C10—C14—C13	50.10 (12)
C1—C6—C7—C3	−56.74 (11)	C9—C10—C14—C13	−56.37 (11)