1,1′-{[1,4-Phenyl­enebis(methyl­ene)]bis­(­oxy)bis­(4,1-phenyl­ene)}diethanone

Al-Mohammed, N.N.; Alias, Y.; Abdullah, Z.; Khaledi, H.

doi:10.1107/S160053681104565X

organic compounds

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Volume 67| Part 12| December 2011| Page o3164

https://doi.org/10.1107/S160053681104565X

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1,1′-{[1,4-Phenylenebis(methylene)]bis(oxy)bis(4,1-phenylene)}diethanone

Nassir N. Al-Mohammed,^a Yatimah Alias,^a Zanariah Abdullah ^a and Hamid Khaledi ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 23 October 2011; accepted 31 October 2011; online 5 November 2011)

The centroid of the central aromatic ring of the title molecule, C₂₄H₂₂O₄, is located on an inversion center. The dihedral angle between the central and terminal benzene rings is 75.00 (7)°. In the crystal, molecules are linked through C—H⋯O hydrogen bonds into chains along [121]. The chains are connected into layers via C—H⋯π interactions.

Related literature

For related structures, see: Al-Mohammed et al. (2011 ); Hu (2010 ); Tang et al. (2008 ).

Experimental

Crystal data

C₂₄H₂₂O₄
M_r = 374.42
Triclinic, $[P \overline 1]$
a = 8.1286 (12) Å
b = 8.1610 (7) Å
c = 8.4878 (6) Å
α = 116.164 (5)°
β = 106.328 (7)°
γ = 100.196 (7)°
V = 454.41 (8) Å³
Z = 1
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.23 × 0.19 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.992
2732 measured reflections
1654 independent reflections
1472 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.07
1654 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.95	2.54	3.4362 (18)	158
C12—H12⋯Cg1ⁱⁱ	0.95	2.61	3.5078 (17)	158
Symmetry codes: (i) -x+2, -y+3, -z+2; (ii) x, y-1, z-1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681104565X/pv2469sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104565X/pv2469Isup2.hkl

checkCIF report

Comment top

We have recently reported the crystal structure of o-acetyl isomer of the title compound (Al-Mohammed et al., 2011). Similar to the previous structure, the title molecule shows a centrosymmetric molecular structure with the centroid of the central benzene ring being located on an inversion center. The central and terminal rings make a dihedral angle of 75.00 (7)°. This value is comparable to those observed in the structures of the previously reported isomer and some other similar compounds (Hu, 2010; Tang et al., 2008). In the crystal, the molecules are linked through C—H···O bonds into chains along [1 2 1] direction. The chains are connected into layers via C—H···π interactions (Table 1, Fig. 2).

Related literature top

For related structures, see: Al-Mohammed et al. (2011); Hu (2010); Tang et al. (2008).

Experimental top

To a suspension of α,α'-dibromo-p-xylene (1 g, 3.8 mmol) and potassium carbonate (1.05 g, 7.57 mmol) in dry acetone (25 ml), 4'-hydroxyacetophenone (1.03 g, 7.57 mmole) was added and the mixture was refluxed for 48 hr. The solvent was then evaporated under reduced pressure and the crude material was extracted with dichloromethane (3 x 25 ml). The combined organic layers were washed with water followed by brine and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum and the formed amorphous solid was re-crystallized from chloroform to obtain colorless crystals of the title compound (m.p. = 435–437 K).

Structure description top

For related structures, see: Al-Mohammed et al. (2011); Hu (2010); Tang et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: A = -x+1, -y+1, -z+1.
	Fig. 2. The two-dimensional network formed by C—H···O and C—H···π interactions (dashed lines).

1,1'-{[1,4-Phenylenebis(methylene)]bis(oxy)bis(4,1-phenylene)}diethanone top

Crystal data top

C₂₄H₂₂O₄	Z = 1
M_r = 374.42	F(000) = 198
Triclinic, P1	D_x = 1.368 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1286 (12) Å	Cell parameters from 1506 reflections
b = 8.1610 (7) Å	θ = 2.9–28.8°
c = 8.4878 (6) Å	µ = 0.09 mm⁻¹
α = 116.164 (5)°	T = 100 K
β = 106.328 (7)°	Block, colorless
γ = 100.196 (7)°	0.23 × 0.19 × 0.09 mm
V = 454.41 (8) Å³

Data collection top

Bruker APEXII CCD diffractometer	1654 independent reflections
Radiation source: fine-focus sealed tube	1472 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 25.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.979, T_max = 0.992	k = −9→9
2732 measured reflections	l = −10→10

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0644P)² + 0.0983P] where P = (F_o² + 2F_c²)/3
1654 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₄H₂₂O₄	γ = 100.196 (7)°
M_r = 374.42	V = 454.41 (8) Å³
Triclinic, P1	Z = 1
a = 8.1286 (12) Å	Mo Kα radiation
b = 8.1610 (7) Å	µ = 0.09 mm⁻¹
c = 8.4878 (6) Å	T = 100 K
α = 116.164 (5)°	0.23 × 0.19 × 0.09 mm
β = 106.328 (7)°

Data collection top

Bruker APEXII CCD diffractometer	1654 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1472 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.992	R_int = 0.020
2732 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.07	Δρ_max = 0.20 e Å⁻³
1654 reflections	Δρ_min = −0.34 e Å⁻³
128 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	1.00611 (13)	1.92652 (14)	1.27797 (14)	0.0228 (3)
O2	0.62238 (13)	1.01503 (13)	0.83520 (13)	0.0192 (3)
C1	1.22612 (19)	1.8825 (2)	1.4939 (2)	0.0246 (3)
H1A	1.2907	2.0214	1.5498	0.037*
H1B	1.3039	1.8086	1.4524	0.037*
H1C	1.1976	1.8627	1.5904	0.037*
C2	1.05129 (18)	1.8131 (2)	1.32364 (19)	0.0179 (3)
C3	0.93621 (18)	1.60305 (19)	1.20855 (18)	0.0166 (3)
C4	0.97991 (18)	1.4674 (2)	1.25479 (18)	0.0174 (3)
H4	1.0826	1.5113	1.3695	0.021*
C5	0.87715 (18)	1.2701 (2)	1.13753 (19)	0.0174 (3)
H5	0.9082	1.1802	1.1722	0.021*
C6	0.72738 (18)	1.20521 (19)	0.96773 (18)	0.0166 (3)
C7	0.67704 (18)	1.3397 (2)	0.92338 (19)	0.0181 (3)
H7	0.5714	1.2964	0.8115	0.022*
C8	0.78030 (19)	1.5347 (2)	1.04150 (19)	0.0181 (3)
H8	0.7455	1.6249	1.0095	0.022*
C9	0.67885 (19)	0.86901 (19)	0.86356 (19)	0.0197 (3)
H9A	0.6449	0.8585	0.9629	0.024*
H9B	0.8132	0.9049	0.9071	0.024*
C10	0.58484 (18)	0.67807 (19)	0.67576 (19)	0.0172 (3)
C11	0.64548 (18)	0.64417 (19)	0.52994 (19)	0.0183 (3)
H11	0.7453	0.7424	0.5498	0.022*
C12	0.56143 (18)	0.4684 (2)	0.35604 (19)	0.0176 (3)
H12	0.6038	0.4474	0.2576	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0258 (6)	0.0168 (5)	0.0241 (5)	0.0062 (4)	0.0077 (4)	0.0111 (4)
O2	0.0205 (5)	0.0115 (5)	0.0182 (5)	0.0045 (4)	0.0024 (4)	0.0057 (4)
C1	0.0232 (7)	0.0162 (7)	0.0236 (7)	0.0013 (6)	0.0030 (6)	0.0080 (6)
C2	0.0192 (7)	0.0161 (7)	0.0177 (7)	0.0052 (6)	0.0089 (6)	0.0079 (6)
C3	0.0171 (7)	0.0161 (7)	0.0164 (7)	0.0052 (6)	0.0080 (5)	0.0078 (6)
C4	0.0174 (7)	0.0185 (7)	0.0137 (6)	0.0064 (5)	0.0050 (5)	0.0071 (6)
C5	0.0206 (7)	0.0160 (7)	0.0178 (7)	0.0079 (6)	0.0078 (6)	0.0099 (6)
C6	0.0178 (7)	0.0143 (7)	0.0158 (7)	0.0041 (5)	0.0076 (6)	0.0064 (6)
C7	0.0181 (7)	0.0179 (7)	0.0151 (6)	0.0056 (6)	0.0041 (5)	0.0078 (6)
C8	0.0207 (7)	0.0172 (7)	0.0190 (7)	0.0080 (6)	0.0078 (6)	0.0111 (6)
C9	0.0226 (7)	0.0154 (7)	0.0190 (7)	0.0077 (6)	0.0046 (6)	0.0091 (6)
C10	0.0184 (7)	0.0143 (7)	0.0190 (7)	0.0080 (5)	0.0050 (5)	0.0094 (6)
C11	0.0168 (7)	0.0165 (7)	0.0225 (7)	0.0050 (5)	0.0060 (5)	0.0124 (6)
C12	0.0194 (7)	0.0184 (7)	0.0189 (7)	0.0089 (6)	0.0083 (5)	0.0115 (6)

Geometric parameters (Å, º) top

O1—C2	1.2240 (16)	C6—C7	1.3967 (19)
O2—C6	1.3617 (17)	C7—C8	1.375 (2)
O2—C9	1.4398 (15)	C7—H7	0.9500
C1—C2	1.5059 (19)	C8—H8	0.9500
C1—H1A	0.9800	C9—C10	1.5020 (18)
C1—H1B	0.9800	C9—H9A	0.9900
C1—H1C	0.9800	C9—H9B	0.9900
C2—C3	1.4866 (19)	C10—C11	1.3931 (19)
C3—C4	1.3964 (19)	C10—C12ⁱ	1.3954 (19)
C3—C8	1.4035 (19)	C11—C12	1.3864 (19)
C4—C5	1.387 (2)	C11—H11	0.9500
C4—H4	0.9500	C12—C10ⁱ	1.3954 (19)
C5—C6	1.3972 (19)	C12—H12	0.9500
C5—H5	0.9500

C6—O2—C9	117.64 (10)	C8—C7—C6	120.06 (12)
C2—C1—H1A	109.5	C8—C7—H7	120.0
C2—C1—H1B	109.5	C6—C7—H7	120.0
H1A—C1—H1B	109.5	C7—C8—C3	121.19 (13)
C2—C1—H1C	109.5	C7—C8—H8	119.4
H1A—C1—H1C	109.5	C3—C8—H8	119.4
H1B—C1—H1C	109.5	O2—C9—C10	108.13 (10)
O1—C2—C3	120.37 (12)	O2—C9—H9A	110.1
O1—C2—C1	120.78 (12)	C10—C9—H9A	110.1
C3—C2—C1	118.84 (12)	O2—C9—H9B	110.1
C4—C3—C8	117.90 (13)	C10—C9—H9B	110.1
C4—C3—C2	122.90 (12)	H9A—C9—H9B	108.4
C8—C3—C2	119.15 (12)	C11—C10—C12ⁱ	118.81 (13)
C5—C4—C3	121.68 (12)	C11—C10—C9	119.68 (13)
C5—C4—H4	119.2	C12ⁱ—C10—C9	121.51 (12)
C3—C4—H4	119.2	C12—C11—C10	120.58 (13)
C4—C5—C6	119.14 (13)	C12—C11—H11	119.7
C4—C5—H5	120.4	C10—C11—H11	119.7
C6—C5—H5	120.4	C11—C12—C10ⁱ	120.60 (12)
O2—C6—C7	115.22 (12)	C11—C12—H12	119.7
O2—C6—C5	124.87 (12)	C10ⁱ—C12—H12	119.7
C7—C6—C5	119.91 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱⁱ	0.95	2.54	3.4362 (18)	158
C12—H12···Cg1ⁱⁱⁱ	0.95	2.61	3.5078 (17)	158

Symmetry codes: (ii) −x+2, −y+3, −z+2; (iii) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂O₄
M_r	374.42
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.1286 (12), 8.1610 (7), 8.4878 (6)
α, β, γ (°)	116.164 (5), 106.328 (7), 100.196 (7)
V (Å³)	454.41 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.19 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	2732, 1654, 1472
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.07
No. of reflections	1654
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.95	2.54	3.4362 (18)	157.6
C12—H12···Cg1ⁱⁱ	0.95	2.61	3.5078 (17)	158

Symmetry codes: (i) −x+2, −y+3, −z+2; (ii) x, y−1, z−1.

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP001/2010 A).

References

Al-Mohammed, N. N. N., Alias, Y., Abdullah, Z. & Khaledi, H. (2011). Acta Cryst. E67, o3016. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, T. (2010). Acta Cryst. E66, o995. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, K.-Z., Tang, Y., Li, Y.-F., Liu, W.-S. & Tan, M.-Y. (2008). Chin. J. Struct. Chem. 27, 451–454. CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3164

https://doi.org/10.1107/S160053681104565X

Open

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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

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		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,1′-{[1,4-Phenyl­enebis(methyl­ene)]bis­­(­­oxy)bis­­(4,1-phenyl­ene)}di­ethanone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,1′-{[1,4-Phenylenebis(methylene)]bis(oxy)bis(4,1-phenylene)}diethanone