2,3-Bis(phenoxy-meth-yl)buta-1,3-diene.

The mol-ecule of the title compound, C(18)H(18)O(2), a symmetrically phenol-substituted divinyl analog, exhibits crystallographically imposed C(2) symmetry. The phenolic and divinyl planar groups inter-sect each other orthogonally, with a dihedral angle of 82.7 (1)°. The structure is stabilized by a short intra-molecular C-H⋯O contact. The mol-ecules are held together by C-H⋯π inter-actions, forming a sheet structure parallel to the (201) plane.

Related literature

The crystal structures of three analogous compounds have been published thus far (Alcock et al., 2006 ▶; Sathiyanarayanan et al., 2007 ▶, 2008 ▶). For mol­ecular and crystal symmetry, see Yao et al. (2002 ▶); Pidcock et al. (2003 ▶); Narasegowda et al. (2005 ▶); Schmidt et al. (2006 ▶).

Experimental

Crystal data

C18H18O2

M = 266.32

Monoclinic,

a = 10.7575 (5) Å

b = 7.0750 (3) Å

c = 9.7939 (5) Å

β = 109.180 (2)°

V = 704.03 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 (2) K

0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.958, T max = 0.981

9151 measured reflections

2065 independent reflections

1558 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 1.02

2065 reflections

127 parameters

All H-atom parameters refined

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063404/bx2124sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063404/bx2124Isup2.hkl

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

C18H18O2	F000 = 284
Mr = 266.32	Dx = 1.256 Mg m−3
Monoclinic, P21/c	Melting point: 364 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 10.7575 (5) Å	Cell parameters from 3326 reflections
b = 7.0750 (3) Å	θ = 3.5–29.4º
c = 9.7939 (5) Å	µ = 0.08 mm−1
β = 109.180 (2)º	T = 295 (2) K
V = 704.03 (6) Å3	Prism, colourless
Z = 2	0.30 × 0.20 × 0.16 mm

Bruker Kappa diffractometer	2065 independent reflections
Radiation source: fine-focus sealed tube	1558 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 295(2) K	θmax = 30.2º
ω and φ–scan	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −15→14
Tmin = 0.958, Tmax = 0.981	k = −9→9
9151 measured reflections	l = −7→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	All H-atom parameters refined
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.069P)2 + 0.0874P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2065 reflections	Δρmax = 0.19 e Å−3
127 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=dPlane 1 m1 = -0.70263(0.00094) m2 = -0.43813(0.00092) m3 = 0.56068(0.00161) D = -5.31928(0.00495) Atom d s d/s (d/s)**2 C7 * 0.0000 0.0013 0.000 0.000 C8 * 0.0000 0.0010 0.000 0.000 C9 * 0.0000 0.0013 0.000 0.000 O1 0.0945 0.0009 108.132 11692.442 ============ Sum((d/s)**2) for starred atoms 0.000Plane 2 m1 = -0.52237(0.00027) m2 = 0.81703(0.00021) m3 = -0.24412(0.00046) D = -0.87330(0.00135) Atom d s d/s (d/s)**2 O1 * -0.0015 0.0009 - 1.703 2.900 C1 * -0.0008 0.0010 - 0.726 0.527 C2 * 0.0022 0.0012 1.889 3.567 C3 * 0.0011 0.0012 0.877 0.769 C4 * -0.0031 0.0013 - 2.359 5.563 C5 * -0.0023 0.0013 - 1.742 3.035 C6 * 0.0048 0.0012 4.058 16.471 C7 - 0.2091 0.0013 - 164.276 26986.654 ============ Sum((d/s)**2) for starred atoms 32.831 Chi-squared at 95% for 4 degrees of freedom: 9.49 The group of atoms deviates significantly from planarityDihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 82.66 (0.06) 97.34 (0.06)

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	0.27879 (10)	0.09878 (14)	−0.21059 (11)	0.0352 (2)
C2	0.19476 (11)	0.00566 (16)	−0.33013 (11)	0.0406 (3)
H2A	0.2117 (13)	0.011 (2)	−0.4223 (16)	0.053 (4)*
C3	0.08982 (12)	−0.09532 (17)	−0.31788 (13)	0.0453 (3)
H3A	0.0324 (14)	−0.158 (2)	−0.4013 (17)	0.056 (4)*
C4	0.06662 (13)	−0.10558 (18)	−0.18746 (14)	0.0486 (3)
H4A	−0.0079 (17)	−0.176 (2)	−0.1799 (18)	0.068 (5)*
C5	0.15010 (13)	−0.01250 (18)	−0.06949 (13)	0.0475 (3)
H5A	0.1334 (14)	−0.017 (2)	0.0254 (17)	0.060 (4)*
C6	0.25622 (12)	0.09092 (16)	−0.07924 (11)	0.0398 (3)
H6A	0.3116 (13)	0.158 (2)	0.0011 (15)	0.048 (3)*
C7	0.48149 (11)	0.26949 (18)	−0.11341 (14)	0.0445 (3)
H7A	0.5603 (15)	0.277 (2)	−0.1465 (17)	0.064 (4)*
H7B	0.5038 (14)	0.180 (2)	−0.0351 (15)	0.046 (3)*
C8	0.45057 (9)	0.46076 (14)	−0.06518 (10)	0.0344 (2)
O1	0.38019 (8)	0.19483 (12)	−0.23461 (9)	0.0474 (2)
C9	0.34154 (12)	0.55102 (19)	−0.13827 (14)	0.0472 (3)
H9B	0.2789 (14)	0.496 (2)	−0.2264 (16)	0.053 (4)*
H9A	0.3180 (16)	0.677 (2)	−0.1096 (18)	0.068 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0346 (5)	0.0316 (5)	0.0387 (5)	0.0011 (4)	0.0112 (4)	−0.0036 (4)
C2	0.0431 (6)	0.0404 (6)	0.0355 (5)	0.0012 (5)	0.0089 (4)	−0.0049 (4)
C3	0.0402 (6)	0.0406 (6)	0.0470 (6)	−0.0019 (5)	0.0033 (5)	−0.0059 (5)
C4	0.0407 (6)	0.0438 (7)	0.0612 (7)	−0.0051 (5)	0.0166 (5)	0.0018 (5)
C5	0.0531 (7)	0.0475 (7)	0.0459 (6)	0.0000 (5)	0.0215 (5)	0.0025 (5)
C6	0.0441 (6)	0.0384 (6)	0.0350 (5)	−0.0006 (5)	0.0103 (4)	−0.0043 (4)
C7	0.0338 (6)	0.0431 (6)	0.0546 (7)	−0.0031 (5)	0.0119 (5)	−0.0096 (5)
C8	0.0316 (5)	0.0335 (5)	0.0377 (5)	−0.0036 (4)	0.0110 (4)	0.0026 (4)
O1	0.0453 (5)	0.0537 (5)	0.0464 (4)	−0.0140 (4)	0.0194 (4)	−0.0128 (4)
C9	0.0408 (6)	0.0432 (6)	0.0481 (6)	0.0011 (5)	0.0019 (5)	0.0026 (5)

C1—O1	1.3695 (13)	C5—H5A	1.003 (16)
C1—C6	1.3865 (14)	C6—H6A	0.944 (14)
C1—C2	1.3880 (14)	C7—O1	1.4232 (14)
C2—C3	1.3741 (17)	C7—C8	1.5060 (15)
C2—H2A	0.979 (15)	C7—H7A	1.003 (16)
C3—C4	1.3816 (18)	C7—H7B	0.961 (15)
C3—H3A	0.958 (16)	C8—C9	1.3206 (16)
C4—C5	1.3759 (18)	C8—C8i	1.476 (2)
C4—H4A	0.967 (17)	C9—H9B	0.983 (15)
C5—C6	1.3854 (17)	C9—H9A	0.991 (17)
O1—C1—C6	124.85 (9)	C5—C6—H6A	121.1 (8)
O1—C1—C2	115.18 (9)	C1—C6—H6A	119.8 (8)
C6—C1—C2	119.97 (10)	O1—C7—C8	114.05 (10)
C3—C2—C1	119.95 (10)	O1—C7—H7A	104.4 (9)
C3—C2—H2A	120.5 (8)	C8—C7—H7A	110.4 (9)
C1—C2—H2A	119.6 (8)	O1—C7—H7B	110.1 (8)
C2—C3—C4	120.75 (11)	C8—C7—H7B	111.3 (8)
C2—C3—H3A	119.1 (9)	H7A—C7—H7B	106.1 (13)
C4—C3—H3A	120.2 (9)	C9—C8—C8i	123.11 (13)
C5—C4—C3	119.00 (11)	C9—C8—C7	120.85 (10)
C5—C4—H4A	120.8 (10)	C8i—C8—C7	116.03 (11)
C3—C4—H4A	120.2 (10)	C1—O1—C7	118.41 (9)
C4—C5—C6	121.34 (11)	C8—C9—H9B	121.1 (8)
C4—C5—H5A	119.8 (9)	C8—C9—H9A	123.0 (10)
C6—C5—H5A	118.9 (9)	H9B—C9—H9A	115.9 (13)
C5—C6—C1	118.99 (10)
O1—C1—C2—C3	179.90 (10)	C2—C1—C6—C5	0.74 (17)
C6—C1—C2—C3	−0.46 (16)	O1—C7—C8—C9	−4.17 (16)
C1—C2—C3—C4	0.00 (17)	C6—C1—O1—C7	9.79 (16)
C2—C3—C4—C5	0.18 (19)	C2—C1—O1—C7	−170.59 (10)
C3—C4—C5—C6	0.11 (19)	C8—C7—O1—C1	−84.83 (13)
C4—C5—C6—C1	−0.57 (18)	O1—C7—C8—C8i	176.68 (10)
O1—C1—C6—C5	−179.66 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1	0.98 (2)	2.41 (2)	2.770 (2)	101 (1)
C4—H4A···Cg1ii	0.97 (2)	2.92 (2)	3.727 (2)	142 (1)
C9—H9A···Cg1iii	0.99 (2)	2.73 (2)	3.591 (1)	146 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O1	0.98 (2)	2.41 (2)	2.770 (2)	101 (1)
C4—H4A⋯Cg1i	0.97 (2)	2.92 (2)	3.727 (2)	142 (1)
C9—H9A⋯Cg1ii	0.99 (2)	2.73 (2)	3.591 (1)	146 (1)

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C1–C6 ring.