4,4′-Bis(prop-2-yn­yloxy)biphen­yl

Zhang, W.; Yao, L.; Tao, R.-J.

doi:10.1107/S160053680706638X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o307

https://doi.org/10.1107/S160053680706638X

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4,4′-Bis(prop-2-ynyloxy)biphenyl

Wu Zhang,^a Li Yao ^b and Ruo-Jie Tao ^a ^*

^aInstitute of Molecular and Crystal Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475001, Henan, People's Republic of China, and ^bSchool of Computer and Information Engineering, Henan University, Kaifeng 475001, Henan, People's Republic of China
^*Correspondence e-mail: rjtao@henu.edu.cn

(Received 21 November 2007; accepted 10 December 2007; online 18 December 2007)

The title compound, C₁₈H₁₄O₂, crystallizes with one half-molecule in the asymmetric unit. The molecule 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 interactions are observed in the crystal structure.

Related literature

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

Experimental

Crystal data

C₁₈H₁₄O₂
M_r = 262.29
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.116
S = 1.08
1392 reflections
91 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706638X/bh2156Isup2.hkl

checkCIF report

Comment top

The title compound has been X-ray characterized (Fig. 1). The molecule lies on an inversion center, placed at the midpoint of the central C—C bond. As a result, all non-H atoms are almost coplanar, with a mean deviation from the least-squares plane of 0.0318 (13) Å. The bond lengths and angles show normal values. The crystal structure is characterized by zigzag chains (Fig. 2 and 3) formed along [100].

Related literature top

The title molecule was obtained unintentionally during an attempt at the synthesis of a Co^II complex, carried out following a published work (Burchell et al., 2006). The title molecule corresponds to a nonreacting ligand.

Experimental top

The title compound was obtained unintentionally as the product of an attempted synthesis of a network complex (Burchell et al., 2006) based on Co^II and 4,4'-bis(prop-2-ynyloxy)biphenyl, by evaporation of a methyl alcohol and acetone solution of CoCl₂, NaN₃ and the title molecule, at 298 K.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); 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 (Sheldrick, 1997).

Figures top

	Fig. 1. The molecular structure of the title molecule, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. 'A' labeled atoms are generated by symmetry code -x, -y, -z.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis.
	Fig. 3. The molecular packing of the title compound, viewed along the b axis.

4,4'-Bis(prop-2-ynyloxy)biphenyl top

Crystal data top

C₁₈H₁₄O₂	F(000) = 552
M_r = 262.29	D_x = 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 = 5.4–55.8°
b = 8.2061 (18) Å	µ = 0.08 mm⁻¹
c = 22.873 (5) Å	T = 293 K
V = 1424.3 (5) Å³	Block, colourless
Z = 4	0.20 × 0.17 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1037 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 26.0°, θ_min = 3.2°
φ and ω scans	h = −9→8
7569 measured reflections	k = −9→10
1392 independent reflections	l = −28→26

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0448P)² + 0.3393P] where P = (F_o² + 2F_c²)/3
1392 reflections	(Δ/σ)_max < 0.001
91 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³
0 constraints

Crystal data top

C₁₈H₁₄O₂	V = 1424.3 (5) Å³
M_r = 262.29	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 7.5881 (16) Å	µ = 0.08 mm⁻¹
b = 8.2061 (18) Å	T = 293 K
c = 22.873 (5) Å	0.20 × 0.17 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1037 reflections with I > 2σ(I)
7569 measured reflections	R_int = 0.040
1392 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.08	Δρ_max = 0.16 e Å⁻³
1392 reflections	Δρ_min = −0.14 e Å⁻³
91 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄O₂
M_r	262.29
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	7.5881 (16), 8.2061 (18), 22.873 (5)
V (Å³)	1424.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.17 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7569, 1392, 1037
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.116, 1.08
No. of reflections	1392
No. of parameters	91
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: APEX2 (Bruker, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2005) and DIAMOND (Brandenburg, 1998).

Acknowledgements

The authors are grateful for financial support provided by the Henan Administration of Science and Technology (grant No. 0111030700).

References

Brandenburg, K. (1998). DIAMOND. Version 2.0. University of Bonn, Germany. Google Scholar
Bruker (2005). APEX2 (Version 1.27) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burchell, T. J., Jennings, M. C. & Puddephatt, R. J. (2006). Inorg. Chim. Acta, 359, 2812–2818. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar