4,4'-Bis(prop-2-yn-yloxy)biphen-yl.

The title compound, C(18)H(14)O(2), crystallizes with one half-mol-ecule in the asymmetric unit. The mol-ecule lies on an inversion center, located at the mid-point of the central C-C bond. As a result, the benzene rings are coplanar. No classical hydrogen bonds or stacking inter-actions are observed in the crystal structure.

Related literature

The title mol­ecule was obtained unintentionally during an attempt at the synthesis of a CoII complex, carried out following a published work (Burchell et al., 2006 ▶).

Experimental

Crystal data

C18H14O2

M = 262.29

Orthorhombic,

a = 7.5881 (16) Å

b = 8.2061 (18) Å

c = 22.873 (5) Å

V = 1424.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.20 × 0.17 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

7569 measured reflections

1392 independent reflections

1037 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.116

S = 1.08

1392 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2005 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706638X/bh2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706638X/bh2156Isup2.hkl

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

C18H14O2	F000 = 552
Mr = 262.29	Dx = 1.223 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1896 reflections
a = 7.5881 (16) Å	θ = 5.4–55.8º
b = 8.2061 (18) Å	µ = 0.08 mm−1
c = 22.873 (5) Å	T = 293 (2) K
V = 1424.3 (5) Å3	Block, colourless
Z = 4	0.20 × 0.17 × 0.15 mm

Bruker APEXII CCD area-detector diffractometer	1037 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Monochromator: graphite	θmax = 26.0º
T = 293(2) K	θmin = 3.2º
φ and ω scans	h = −9→8
Absorption correction: none	k = −9→10
7569 measured reflections	l = −28→26
1392 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.3393P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1392 reflections	Δρmax = 0.16 e Å−3
91 parameters	Δρmin = −0.14 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
C1	0.0440 (4)	0.7955 (3)	0.21976 (10)	0.0956 (9)
H1	0.0256	0.8708	0.2495	0.115*
C2	0.0669 (3)	0.7021 (2)	0.18279 (8)	0.0636 (5)
C3	0.0975 (3)	0.5881 (2)	0.13510 (8)	0.0587 (5)
H3A	0.0660	0.6382	0.0981	0.070*
H3B	0.2212	0.5586	0.1336	0.070*
C4	0.0023 (2)	0.32626 (19)	0.10298 (7)	0.0408 (4)
C5	−0.0877 (2)	0.1838 (2)	0.11486 (7)	0.0474 (4)
H5A	−0.1484	0.1728	0.1500	0.057*
C6	−0.0879 (2)	0.0580 (2)	0.07515 (7)	0.0465 (4)
H6A	−0.1493	−0.0369	0.0842	0.056*
C7	0.0007 (2)	0.06755 (18)	0.02165 (6)	0.0381 (4)
C8	0.0918 (2)	0.2113 (2)	0.01155 (7)	0.0483 (5)
H8A	0.1545	0.2222	−0.0232	0.058*
C9	0.0934 (2)	0.3391 (2)	0.05092 (7)	0.0493 (5)
H9A	0.1558	0.4337	0.0424	0.059*
O1	−0.00711 (15)	0.44653 (14)	0.14459 (5)	0.0507 (4)

	U11	U22	U33	U12	U13	U23
C1	0.139 (3)	0.0774 (17)	0.0706 (14)	−0.0022 (17)	0.0079 (14)	−0.0255 (13)
C2	0.0802 (14)	0.0552 (12)	0.0554 (11)	−0.0051 (11)	0.0010 (10)	−0.0046 (10)
C3	0.0691 (13)	0.0485 (11)	0.0586 (11)	−0.0098 (10)	0.0079 (10)	−0.0049 (9)
C4	0.0390 (9)	0.0414 (9)	0.0421 (8)	0.0028 (8)	−0.0008 (7)	0.0011 (7)
C5	0.0483 (10)	0.0518 (11)	0.0421 (9)	−0.0054 (8)	0.0082 (8)	0.0036 (8)
C6	0.0485 (10)	0.0439 (10)	0.0470 (9)	−0.0094 (8)	0.0049 (8)	0.0042 (8)
C7	0.0323 (8)	0.0388 (9)	0.0431 (8)	0.0033 (7)	−0.0009 (7)	0.0052 (7)
C8	0.0523 (10)	0.0459 (10)	0.0468 (9)	−0.0057 (8)	0.0132 (8)	0.0021 (8)
C9	0.0541 (11)	0.0407 (10)	0.0531 (10)	−0.0093 (8)	0.0111 (8)	0.0018 (8)
O1	0.0577 (8)	0.0463 (7)	0.0480 (6)	−0.0062 (6)	0.0081 (6)	−0.0044 (6)

C1—C2	1.155 (3)	C5—C6	1.375 (2)
C1—H1	0.9300	C5—H5A	0.9300
C2—C3	1.456 (3)	C6—C7	1.399 (2)
C3—O1	1.424 (2)	C6—H6A	0.9300
C3—H3A	0.9700	C7—C8	1.386 (2)
C3—H3B	0.9700	C7—C7i	1.487 (3)
C4—O1	1.3729 (19)	C8—C9	1.382 (2)
C4—C5	1.381 (2)	C8—H8A	0.9300
C4—C9	1.381 (2)	C9—H9A	0.9300
C2—C1—H1	180.0	C5—C6—C7	122.35 (15)
C1—C2—C3	178.3 (2)	C5—C6—H6A	118.8
O1—C3—C2	108.71 (15)	C7—C6—H6A	118.8
O1—C3—H3A	109.9	C8—C7—C6	115.68 (14)
C2—C3—H3A	109.9	C8—C7—C7i	121.82 (17)
O1—C3—H3B	109.9	C6—C7—C7i	122.50 (17)
C2—C3—H3B	109.9	C9—C8—C7	122.78 (15)
H3A—C3—H3B	108.3	C9—C8—H8A	118.6
O1—C4—C5	116.53 (14)	C7—C8—H8A	118.6
O1—C4—C9	124.67 (15)	C4—C9—C8	119.95 (15)
C5—C4—C9	118.80 (15)	C4—C9—H9A	120.0
C6—C5—C4	120.43 (15)	C8—C9—H9A	120.0
C6—C5—H5A	119.8	C4—O1—C3	116.87 (12)
C4—C5—H5A	119.8
O1—C4—C5—C6	178.87 (15)	O1—C4—C9—C8	−178.91 (16)
C9—C4—C5—C6	−0.8 (2)	C5—C4—C9—C8	0.7 (3)
C4—C5—C6—C7	−0.1 (3)	C7—C8—C9—C4	0.3 (3)
C5—C6—C7—C8	1.1 (2)	C5—C4—O1—C3	174.67 (16)
C5—C6—C7—C7i	−179.38 (18)	C9—C4—O1—C3	−5.7 (2)
C6—C7—C8—C9	−1.2 (2)	C2—C3—O1—C4	178.71 (15)
C7i—C7—C8—C9	179.30 (18)