2,3-Bis[(2-methyl-phen-oxy)meth-yl]buta-1,3-diene.

The mol-ecule of the title compound, C(20)H(22)O(2), a symmetrically 2-methyl-phenol-substituted divinyl analog, exhibits crystallographically imposed C(2) symmetry. The mol-ecular structure is essentially planar. The structure is stabilized by a short inter-molecular C-H⋯O contact. Cooperative C-H⋯π inter-actions generate an infinite one-dimensional chain of mol-ecules along the a axis.

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

C20H22O2

M = 294.38

Monoclinic,

a = 5.2241 (5) Å

b = 21.6274 (19) Å

c = 7.5101 (7) Å

β = 102.044 (4)°

V = 829.84 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 295 (2) K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.973, T max = 0.980

7281 measured reflections

1632 independent reflections

1352 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.141

S = 1.15

1632 reflections

143 parameters

All H-atom parameters refined

Δρmax = 0.20 e Å−3

Δρmin = −0.15 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/S1600536807063398/bx2123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063398/bx2123Isup2.hkl

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

C20H22O2	F000 = 316
Mr = 294.38	Dx = 1.178 Mg m−3
Monoclinic, P21/n	Melting point: 346 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 5.2241 (5) Å	Cell parameters from 4455 reflections
b = 21.6274 (19) Å	θ = 2.8–31.0º
c = 7.5101 (7) Å	µ = 0.07 mm−1
β = 102.044 (4)º	T = 295 (2) K
V = 829.84 (13) Å3	Prism, colourless
Z = 2	0.22 × 0.18 × 0.16 mm

BrukerKkappa diffractometer	1632 independent reflections
Radiation source: fine-focus sealed tube	1352 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 295(2) K	θmax = 26.0º
ω and φ–scan	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −6→6
Tmin = 0.973, Tmax = 0.980	k = −25→26
7281 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060	All H-atom parameters refined
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0254P)2 + 0.7904P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max = 0.001
1632 reflections	Δρmax = 0.20 e Å−3
143 parameters	Δρmin = −0.15 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 = -0.65734(0.00051) m2 = -0.66742(0.00044) m3 = -0.34994(0.00085) D = -3.59801(0.00113) Atom d s d/s (d/s)**2 O1 * 0.0138 0.0018 7.856 61.715 C1 * -0.0049 0.0023 - 2.109 4.447 C2 * 0.0165 0.0026 6.321 39.959 C3 * 0.0134 0.0027 4.955 24.548 C4 * -0.0055 0.0027 - 2.046 4.184 C5 * -0.0199 0.0026 - 7.572 57.329 C6 * -0.0077 0.0022 - 3.472 12.052 C7 * -0.0354 0.0037 - 9.660 93.324 C8 0.0645 0.0024 26.886 722.869 C9 0.1395 0.0021 64.912 4213.542 C10 0.1687 0.0030 56.080 3144.964 ============ Sum((d/s)**2) for starred atoms 297.558 Chi-squared at 95% for 5 degrees of freedom: 11.10 The group of atoms deviates significantly from planarityPlane 2 m1 = -0.68850(0.00264) m2 = -0.62945(0.00157) m3 = -0.36022(0.00316) D = -3.60224(0.00936) Atom d s d/s (d/s)**2 C8 * 0.0000 0.0024 0.000 0.000 C9 * 0.0000 0.0021 0.000 0.000 C10 * 0.0000 0.0030 0.000 0.000 O1 - 0.0218 0.0018 - 12.401 153.784 ============ Sum((d/s)**2) for starred atoms 0.000Plane 3 m1 = -0.67385(0.00031) m2 = -0.65235(0.00031) m3 = -0.34694(0.00075) D = -3.56623(0.00074) Atom d s d/s (d/s)**2 O1 * -0.0381 0.0018 - 21.735 472.397 C1 * -0.0064 0.0023 - 2.735 7.482 C2 * 0.0453 0.0026 17.389 302.387 C3 * 0.0520 0.0027 19.220 369.400 C4 * 0.0123 0.0027 4.532 20.540 C5 * -0.0327 0.0026 - 12.442 154.803 C6 * -0.0301 0.0022 - 13.569 184.128 C7 * -0.0475 0.0037 - 12.943 167.509 C8 * -0.0100 0.0024 - 4.185 17.517 C9 * 0.0345 0.0021 16.077 258.455 C10 * 0.0611 0.0030 20.305 412.299 ============ Sum((d/s)**2) for starred atoms 2366.918 Chi-squared at 95% for 8 degrees of freedom: 15.50 The group of atoms deviates significantly from planarityDihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 2.88 (0.12) 177.12 (0.12) 1 3 1.29 (0.03) 178.71 (0.03) 2 3 1.73 (0.13) 178.27 (0.13)

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	0.3342 (4)	0.14009 (11)	0.2814 (3)	0.0386 (5)
C2	0.1449 (5)	0.18556 (12)	0.2633 (4)	0.0464 (6)
H2	0.055 (5)	0.1937 (12)	0.369 (4)	0.056*
C3	0.0729 (5)	0.21981 (12)	0.1049 (4)	0.0501 (7)
H3	−0.070 (5)	0.2516 (13)	0.098 (4)	0.059 (8)*
C4	0.1911 (5)	0.20830 (12)	−0.0385 (4)	0.0504 (7)
H4	0.151 (6)	0.2322 (14)	−0.150 (4)	0.071 (9)*
C5	0.3809 (5)	0.16273 (12)	−0.0253 (3)	0.0459 (6)
H5	0.466 (5)	0.1542 (11)	−0.125 (3)	0.045 (7)*
C6	0.4503 (4)	0.12846 (10)	0.1331 (3)	0.0368 (5)
C7	0.4171 (7)	0.10395 (17)	0.4548 (4)	0.0592 (8)
H7A	0.416 (6)	0.0576 (17)	0.432 (4)	0.081 (10)*
H7B	0.297 (7)	0.1125 (16)	0.537 (5)	0.095 (12)*
H7C	0.601 (8)	0.1140 (18)	0.512 (5)	0.108 (14)*
C8	0.7492 (5)	0.06522 (11)	0.0126 (3)	0.0378 (5)
C9	0.9288 (4)	0.01133 (10)	0.0684 (3)	0.0354 (5)
C10	0.9538 (6)	−0.01399 (14)	0.2310 (4)	0.0532 (7)
O1	0.6296 (3)	0.08156 (8)	0.1591 (2)	0.0478 (5)
H8A	0.608 (5)	0.0526 (10)	−0.094 (3)	0.037 (6)*
H8B	0.848 (5)	0.1015 (12)	−0.019 (3)	0.044 (7)*
H10A	1.075 (5)	−0.0505 (13)	0.270 (4)	0.058 (8)*
H10B	0.863 (5)	0.0022 (12)	0.318 (4)	0.053 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0386 (12)	0.0410 (13)	0.0358 (12)	−0.0014 (10)	0.0069 (9)	−0.0044 (10)
C2	0.0435 (14)	0.0495 (15)	0.0480 (14)	0.0027 (11)	0.0135 (11)	−0.0113 (11)
C3	0.0456 (14)	0.0426 (15)	0.0612 (17)	0.0109 (12)	0.0089 (12)	−0.0008 (12)
C4	0.0504 (15)	0.0459 (15)	0.0548 (16)	0.0070 (12)	0.0106 (12)	0.0122 (12)
C5	0.0493 (14)	0.0476 (15)	0.0439 (14)	0.0086 (11)	0.0166 (11)	0.0087 (11)
C6	0.0341 (11)	0.0344 (12)	0.0422 (12)	0.0028 (9)	0.0085 (9)	−0.0006 (10)
C7	0.072 (2)	0.069 (2)	0.0381 (14)	0.0117 (17)	0.0150 (14)	0.0041 (13)
C8	0.0373 (12)	0.0397 (13)	0.0365 (12)	0.0060 (10)	0.0085 (10)	0.0012 (10)
C9	0.0299 (11)	0.0389 (12)	0.0362 (12)	0.0012 (9)	0.0042 (9)	−0.0009 (9)
C10	0.0617 (17)	0.0565 (17)	0.0434 (14)	0.0210 (14)	0.0156 (12)	0.0080 (12)
O1	0.0539 (11)	0.0516 (11)	0.0405 (9)	0.0211 (8)	0.0158 (8)	0.0076 (8)

C1—C2	1.381 (3)	C7—H7A	1.02 (3)
C1—C6	1.397 (3)	C7—H7B	0.99 (4)
C1—C7	1.504 (4)	C7—H7C	0.99 (4)
C2—C3	1.385 (4)	C8—O1	1.418 (3)
C2—H2	1.02 (3)	C8—C9	1.500 (3)
C3—C4	1.372 (4)	C8—H8A	1.01 (2)
C3—H3	1.01 (3)	C8—H8B	1.00 (2)
C4—C5	1.387 (3)	C9—C10	1.320 (3)
C4—H4	0.97 (3)	C9—C9i	1.472 (4)
C5—C6	1.384 (3)	C10—H10A	1.02 (3)
C5—H5	0.97 (2)	C10—H10B	0.95 (3)
C6—O1	1.367 (3)
C2—C1—C6	118.1 (2)	C1—C7—H7B	110 (2)
C2—C1—C7	121.8 (2)	H7A—C7—H7B	108 (3)
C6—C1—C7	120.1 (2)	C1—C7—H7C	110 (2)
C1—C2—C3	121.7 (2)	H7A—C7—H7C	105 (3)
C1—C2—H2	119.0 (15)	H7B—C7—H7C	112 (3)
C3—C2—H2	119.3 (15)	O1—C8—C9	109.15 (18)
C4—C3—C2	119.4 (2)	O1—C8—H8A	108.4 (13)
C4—C3—H3	122.2 (16)	C9—C8—H8A	108.9 (13)
C2—C3—H3	118.3 (16)	O1—C8—H8B	109.0 (14)
C3—C4—C5	120.3 (2)	C9—C8—H8B	110.8 (14)
C3—C4—H4	122.0 (18)	H8A—C8—H8B	110.6 (19)
C5—C4—H4	117.7 (18)	C10—C9—C9i	122.7 (3)
C6—C5—C4	119.8 (2)	C10—C9—C8	121.1 (2)
C6—C5—H5	119.1 (15)	C9i—C9—C8	116.2 (2)
C4—C5—H5	121.1 (15)	C9—C10—H10A	121.5 (15)
O1—C6—C5	124.7 (2)	C9—C10—H10B	120.9 (16)
O1—C6—C1	114.7 (2)	H10A—C10—H10B	118 (2)
C5—C6—C1	120.6 (2)	C6—O1—C8	118.28 (17)
C1—C7—H7A	112.0 (18)
C6—C1—C2—C3	−1.0 (4)	C7—C1—C6—O1	2.4 (3)
C7—C1—C2—C3	178.5 (3)	C2—C1—C6—C5	1.5 (3)
C1—C2—C3—C4	0.3 (4)	C7—C1—C6—C5	−178.1 (3)
C2—C3—C4—C5	0.1 (4)	O1—C8—C9—C10	0.9 (3)
C3—C4—C5—C6	0.4 (4)	C5—C6—O1—C8	−1.8 (3)
C4—C5—C6—O1	178.3 (2)	C1—C6—O1—C8	177.6 (2)
C4—C5—C6—C1	−1.1 (4)	C9—C8—O1—C6	−177.60 (19)
C2—C1—C6—O1	−178.0 (2)	O1—C8—C9—C9i	−179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1	0.95 (3)	2.29 (3)	2.655 (4)	102 (2)
C8—H8B···Cg1ii	1.00 (2)	2.70 (3)	3.534 (3)	141 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1	0.95 (3)	2.29 (3)	2.655 (4)	102 (2)
C8—H8B⋯Cg1i	1.00 (2)	2.70 (3)	3.534 (3)	141 (2)

Symmetry code: (i) . Cg1 is the centroid of the C1–C6 ring.