4-[2-(Cyclo-hexa-1,4-dien-1-yl)eth-oxy]benzene-1,2-dicarbonitrile.

In the title compound, C(16)H(14)N(2)O, the dihedral angle between the aromatic rings is 70.23 (6)°. The linking chain has a zigzag conformation. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯N hydrogen bonds, forming a zigzag chain along the c axis.

Related literature

For background to the use of phthalonitriles and phthalocyanines, see: McKeown (1998 ▶); Leznoff & Lever (1989–1996 ▶); Moser & Thomas (1983 ▶). For the crystal structures of related cyclo­hexa-1,4-dienyl rings, see: Dialer et al. (2004 ▶); Jandacek & Simonsen (1969 ▶); Therrien & Süss-Fink (2006 ▶); Lou & Hu (2009 ▶). For further synthetic details, see: Menzek et al. (2008 ▶). For C N bond lengths, see: Nesi et al. (1998 ▶); Ocak Ískeleli et al. (2005 ▶); Subbiah Pandi et al. (2002 ▶); Yu et al. (2010 ▶). For the Hirshfeld Rigid-Bond test, see: Hirshfeld (1976 ▶).

Experimental

Crystal data

C16H14N2O

M = 250.29

Orthorhombic,

a = 8.6291 (3) Å

b = 27.5913 (14) Å

c = 11.7246 (5) Å

V = 2791.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.45 × 0.37 × 0.32 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.968, T max = 0.983

19074 measured reflections

2790 independent reflections

1901 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.139

S = 1.07

19074 reflections

172 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.13 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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/S1600536811042164/fk2042sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042164/fk2042Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042164/fk2042Isup3.cml

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

C16H14N2O	F(000) = 1056
Mr = 250.29	Dx = 1.191 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 19074 reflections
a = 8.6291 (3) Å	θ = 1.5–26.2°
b = 27.5913 (14) Å	µ = 0.08 mm−1
c = 11.7246 (5) Å	T = 296 K
V = 2791.5 (2) Å3	Block, colorless
Z = 8	0.45 × 0.37 × 0.32 mm

Stoe IPDS 2 diffractometer	2790 independent reflections
Radiation source: fine-focus sealed tube	1901 reflections with I > 2σ(I)
graphite	Rint = 0.047
rotation method scans	θmax = 26.2°, θmin = 1.5°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −10→10
Tmin = 0.968, Tmax = 0.983	k = −34→34
19074 measured reflections	l = −14→14

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0714P)2 + 0.1026P] where P = (Fo2 + 2Fc2)/3
19074 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.11 e Å−3
2 restraints	Δρmin = −0.13 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	−0.0085 (2)	0.17483 (7)	0.35845 (15)	0.0732 (5)
C2	−0.1054 (3)	0.17362 (9)	0.45699 (19)	0.1004 (7)
H2A	−0.0401	0.1683	0.5232	0.120*
H2B	−0.1738	0.1459	0.4504	0.120*
C3	−0.2008 (3)	0.21659 (12)	0.4786 (2)	0.1193 (9)
H3	−0.2667	0.2169	0.5413	0.143*
C4	−0.1957 (3)	0.25488 (11)	0.4112 (3)	0.1166 (9)
H4	−0.2589	0.2812	0.4279	0.140*
C5	−0.0983 (4)	0.25734 (10)	0.3152 (3)	0.1248 (9)
H5A	−0.0287	0.2846	0.3250	0.150*
H5B	−0.1620	0.2640	0.2489	0.150*
C6	−0.0055 (3)	0.21439 (9)	0.2917 (2)	0.1004 (7)
H6	0.0585	0.2144	0.2278	0.120*
C7	0.0900 (3)	0.13131 (8)	0.33115 (18)	0.0918 (6)
H7A	0.0266	0.1023	0.3346	0.110*
H7B	0.1298	0.1343	0.2541	0.110*
C8	0.2225 (2)	0.12638 (8)	0.41224 (16)	0.0822 (5)
H8A	0.2832	0.1560	0.4132	0.099*
H8B	0.1843	0.1204	0.4888	0.099*
C9	0.4477 (2)	0.07643 (6)	0.43332 (14)	0.0665 (4)
C10	0.4881 (2)	0.09851 (6)	0.53531 (14)	0.0686 (4)
H10	0.4238	0.1218	0.5675	0.082*
C11	0.6245 (2)	0.08556 (6)	0.58867 (14)	0.0663 (4)
C12	0.7225 (2)	0.05090 (6)	0.54140 (14)	0.0690 (4)
C13	0.6805 (2)	0.02936 (6)	0.43832 (14)	0.0724 (5)
H13	0.7451	0.0063	0.4053	0.087*
C14	0.5449 (2)	0.04191 (6)	0.38548 (14)	0.0702 (5)
H14	0.5177	0.0272	0.3170	0.084*
C15	0.6671 (2)	0.10975 (7)	0.69314 (16)	0.0772 (5)
C16	0.8642 (2)	0.03802 (7)	0.59768 (17)	0.0810 (5)
N1	0.7011 (2)	0.12993 (7)	0.77426 (15)	0.1066 (6)
N2	0.9776 (2)	0.02813 (8)	0.64194 (17)	0.1077 (6)
O1	0.31679 (15)	0.08620 (5)	0.37450 (10)	0.0824 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0677 (11)	0.0829 (11)	0.0690 (10)	−0.0002 (9)	−0.0071 (8)	−0.0004 (9)
C2	0.0990 (15)	0.1089 (16)	0.0931 (14)	0.0081 (13)	0.0154 (12)	0.0115 (12)
C3	0.111 (2)	0.155 (3)	0.0922 (15)	0.0361 (18)	0.0114 (14)	−0.0140 (17)
C4	0.123 (2)	0.1029 (19)	0.124 (2)	0.0322 (16)	−0.0330 (18)	−0.0331 (17)
C5	0.125 (2)	0.0928 (17)	0.156 (3)	0.0011 (15)	−0.031 (2)	0.0192 (17)
C6	0.0925 (15)	0.1142 (18)	0.0944 (14)	−0.0011 (13)	0.0070 (12)	0.0216 (13)
C7	0.0899 (14)	0.1034 (15)	0.0820 (12)	0.0126 (12)	−0.0152 (11)	−0.0191 (11)
C8	0.0801 (12)	0.0911 (13)	0.0752 (10)	0.0164 (10)	−0.0095 (9)	−0.0200 (10)
C9	0.0712 (11)	0.0671 (10)	0.0614 (9)	0.0016 (8)	0.0002 (8)	−0.0007 (7)
C10	0.0719 (11)	0.0701 (10)	0.0638 (9)	0.0034 (8)	0.0014 (8)	−0.0063 (8)
C11	0.0699 (10)	0.0668 (10)	0.0622 (8)	−0.0031 (8)	0.0018 (8)	0.0029 (7)
C12	0.0719 (10)	0.0657 (10)	0.0693 (9)	−0.0004 (8)	0.0043 (8)	0.0126 (8)
C13	0.0825 (12)	0.0655 (10)	0.0692 (10)	0.0078 (9)	0.0106 (9)	0.0038 (8)
C14	0.0858 (12)	0.0653 (10)	0.0597 (9)	0.0038 (9)	0.0046 (8)	−0.0030 (7)
C15	0.0802 (12)	0.0800 (12)	0.0714 (10)	−0.0017 (10)	−0.0091 (9)	−0.0026 (8)
C16	0.0802 (11)	0.0812 (12)	0.0816 (11)	0.0078 (10)	−0.0013 (9)	0.0094 (9)
N1	0.1198 (15)	0.1121 (14)	0.0877 (11)	−0.0017 (11)	−0.0250 (10)	−0.0168 (10)
N2	0.0960 (14)	0.1210 (15)	0.1059 (14)	0.0233 (11)	−0.0129 (11)	0.0093 (11)
O1	0.0831 (9)	0.0900 (8)	0.0740 (7)	0.0161 (7)	−0.0133 (6)	−0.0210 (6)

C1—C6	1.344 (3)	C8—O1	1.445 (2)
C1—C2	1.426 (3)	C8—H8A	0.9700
C1—C7	1.506 (3)	C8—H8B	0.9700
C2—C3	1.465 (3)	C9—O1	1.351 (2)
C2—H2A	0.9700	C9—C10	1.386 (2)
C2—H2B	0.9700	C9—C14	1.387 (2)
C3—C4	1.319 (4)	C10—C11	1.380 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.406 (4)	C11—C12	1.392 (2)
C4—H4	0.9300	C11—C15	1.443 (3)
C5—C6	1.457 (4)	C12—C13	1.395 (2)
C5—H5A	0.9700	C12—C16	1.434 (3)
C5—H5B	0.9700	C13—C14	1.369 (3)
C6—H6	0.9300	C13—H13	0.9300
C7—C8	1.493 (3)	C14—H14	0.9300
C7—H7A	0.9700	C15—N1	1.141 (2)
C7—H7B	0.9700	C16—N2	1.141 (2)
C6—C1—C2	120.2 (2)	H7A—C7—H7B	107.9
C6—C1—C7	120.86 (19)	O1—C8—C7	107.84 (14)
C2—C1—C7	118.99 (18)	O1—C8—H8A	110.1
C1—C2—C3	116.8 (2)	C7—C8—H8A	110.1
C1—C2—H2A	108.1	O1—C8—H8B	110.1
C3—C2—H2A	108.1	C7—C8—H8B	110.1
C1—C2—H2B	108.1	H8A—C8—H8B	108.5
C3—C2—H2B	108.1	O1—C9—C10	124.26 (15)
H2A—C2—H2B	107.3	O1—C9—C14	115.85 (15)
C4—C3—C2	121.7 (2)	C10—C9—C14	119.89 (16)
C4—C3—H3	119.1	C11—C10—C9	119.46 (16)
C2—C3—H3	119.1	C11—C10—H10	120.3
C3—C4—C5	122.5 (2)	C9—C10—H10	120.3
C3—C4—H4	118.7	C10—C11—C12	121.04 (16)
C5—C4—H4	118.7	C10—C11—C15	118.87 (16)
C4—C5—C6	116.2 (2)	C12—C11—C15	120.06 (16)
C4—C5—H5A	108.2	C11—C12—C13	118.68 (16)
C6—C5—H5A	108.2	C11—C12—C16	120.35 (16)
C4—C5—H5B	108.2	C13—C12—C16	120.98 (17)
C6—C5—H5B	108.2	C14—C13—C12	120.43 (17)
H5A—C5—H5B	107.4	C14—C13—H13	119.8
C1—C6—C5	122.6 (2)	C12—C13—H13	119.8
C1—C6—H6	118.7	C13—C14—C9	120.50 (16)
C5—C6—H6	118.7	C13—C14—H14	119.8
C8—C7—C1	111.70 (15)	C9—C14—H14	119.8
C8—C7—H7A	109.3	N1—C15—C11	178.3 (2)
C1—C7—H7A	109.3	N2—C16—C12	179.3 (2)
C8—C7—H7B	109.3	C9—O1—C8	117.90 (13)
C1—C7—H7B	109.3
C6—C1—C2—C3	1.2 (3)	C9—C10—C11—C15	178.35 (16)
C7—C1—C2—C3	−179.0 (2)	C10—C11—C12—C13	0.1 (2)
C1—C2—C3—C4	−1.0 (4)	C15—C11—C12—C13	−177.84 (16)
C2—C3—C4—C5	−0.5 (4)	C10—C11—C12—C16	179.71 (16)
C3—C4—C5—C6	1.7 (4)	C15—C11—C12—C16	1.8 (2)
C2—C1—C6—C5	0.1 (3)	C11—C12—C13—C14	−0.5 (3)
C7—C1—C6—C5	−179.7 (2)	C16—C12—C13—C14	179.92 (16)
C4—C5—C6—C1	−1.5 (4)	C12—C13—C14—C9	0.4 (3)
C6—C1—C7—C8	107.6 (2)	O1—C9—C14—C13	−179.97 (15)
C2—C1—C7—C8	−72.2 (3)	C10—C9—C14—C13	0.1 (3)
C1—C7—C8—O1	−175.64 (17)	C10—C9—O1—C8	8.2 (3)
O1—C9—C10—C11	179.61 (16)	C14—C9—O1—C8	−171.72 (16)
C14—C9—C10—C11	−0.5 (3)	C7—C8—O1—C9	177.27 (17)
C9—C10—C11—C12	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N2i	0.93	2.56	3.453 (3)	162.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N2i	0.93	2.56	3.453 (3)	162

Symmetry code: (i) .