1,1′-{2,2′-[1,4-Phenyl­enebis(methyl­ene)]bis­(­oxy)bis­(2,1-phenyl­ene)}diethanone

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

doi:10.1107/S1600536811042528

organic compounds

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doi:10.1107/S1600536811042528

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1,1′-{2,2′-[1,4-Phenylenebis(methylene)]bis(oxy)bis(2,1-phenylene)}diethanone

Nassir N. 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 10 October 2011; accepted 13 October 2011; online 22 October 2011)

The asymmetric unit of the title compound, C₂₄H₂₂O₄, contains one half-molecule, the other half being generated by a crystallographic center of inversion. The central benzene ring makes a dihedral angle of 72.49 (5)° with the terminal benzene ring. In the crystal, adjacent molecules are linked through C—H⋯O interactions, forming a sheet structure parallel to the bc plane. The sheets are stacked along the a axis via π–π interactions formed between the terminal benzene rings [centroid–centroid separation = 3.7276 (6) Å].

Related literature

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

Experimental

Crystal data

C₂₄H₂₂O₄
M_r = 374.42
Orthorhombic, P b c a
a = 6.8490 (1) Å
b = 15.0815 (2) Å
c = 17.8519 (3) Å
V = 1843.98 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.969, T_max = 0.986
15454 measured reflections
2013 independent reflections
1728 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.100
S = 1.06
2013 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1ⁱ	0.95	2.56	3.4649 (14)	158
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536811042528/is2792sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042528/is2792Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042528/is2792Isup3.cml

checkCIF report

Comment top

The title compound was obtained through the condensation of α,α'-dibromo-p-xylene with two equivalents of 2'-hydroxyacetophenone. The compound has a centrosymmetric molecular structure, the centroid of the central aromatic ring being located on an inversion center. The central aromatic ring makes a dihedral angle of 72.49 (5)° with the terminal rings. This value is comparable to those observed in similar structures (Hu, 2010; Tang et al., 2008). In the crystal, the adjacent molecules are linked through C—H···O interactions (Table 1) to form a sheet parallel to the bc plane (Fig. 2). The sheets are connected into a three-dimensional network via π–π interactions formed between the terminal rings in the a direction [centroid-centroid separation = 3.7276 (6) Å].

Related literature top

For related structures, see: 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, 7.6 mmol) in dry acetone (25 ml), 2'-hydroxyacetophenone (1.03 g, 7.6 mmol) was added portionwise and the mixture was refluxed for 48 hr. The solvent was then evaporated under reduced pressure and the crude material was extracted by dichloromethane (3 × 25 ml). The combined organic layers was washed with water and 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 off-white crystals of the title compound (m.p. = 435–437 K).

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: ' = -x, -y, -z.]
	Fig. 2. The two-dimensional network in the bc plane formed by C—H···O interactions (dashed lines).

1-(2-{4-[(2-Acetylphenoxy)methyl]benzyloxy}phenyl)ethanone top

Crystal data top

C₂₄H₂₂O₄	F(000) = 792
M_r = 374.42	D_x = 1.349 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4755 reflections
a = 6.8490 (1) Å	θ = 2.7–30.5°
b = 15.0815 (2) Å	µ = 0.09 mm⁻¹
c = 17.8519 (3) Å	T = 100 K
V = 1843.98 (5) Å³	Block, colorless
Z = 4	0.35 × 0.21 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	2013 independent reflections
Radiation source: fine-focus sealed tube	1728 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.969, T_max = 0.986	k = −19→19
15454 measured reflections	l = −22→22

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0539P)² + 0.5451P] where P = (F_o² + 2F_c²)/3
2013 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₄H₂₂O₄	V = 1843.98 (5) Å³
M_r = 374.42	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 6.8490 (1) Å	µ = 0.09 mm⁻¹
b = 15.0815 (2) Å	T = 100 K
c = 17.8519 (3) Å	0.35 × 0.21 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	2013 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1728 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.986	R_int = 0.029
15454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
2013 reflections	Δρ_min = −0.21 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	0.04377 (13)	0.42646 (5)	0.16533 (5)	0.0229 (2)
O2	0.04118 (12)	0.15272 (5)	0.15468 (4)	0.0159 (2)
C1	0.07382 (18)	0.31010 (8)	0.07811 (6)	0.0203 (3)
H1A	−0.0462	0.2780	0.0654	0.031*
H1B	0.1854	0.2696	0.0751	0.031*
H1C	0.0925	0.3591	0.0428	0.031*
C2	0.05802 (16)	0.34623 (7)	0.15636 (6)	0.0165 (3)
C3	0.05993 (16)	0.28692 (7)	0.22360 (6)	0.0146 (2)
C4	0.06897 (16)	0.32882 (8)	0.29338 (6)	0.0171 (3)
H4	0.0753	0.3917	0.2950	0.020*
C5	0.06905 (17)	0.28253 (8)	0.35995 (7)	0.0187 (3)
H5	0.0761	0.3130	0.4065	0.022*
C6	0.05866 (16)	0.19058 (8)	0.35781 (6)	0.0177 (3)
H6	0.0586	0.1579	0.4033	0.021*
C7	0.04836 (16)	0.14611 (7)	0.29006 (6)	0.0160 (2)
H7	0.0401	0.0832	0.2893	0.019*
C8	0.05005 (15)	0.19348 (7)	0.22261 (6)	0.0140 (2)
C9	0.02559 (17)	0.05749 (7)	0.15472 (6)	0.0162 (2)
H9A	−0.0921	0.0387	0.1828	0.019*
H9B	0.1417	0.0308	0.1789	0.019*
C10	0.01168 (16)	0.02795 (7)	0.07449 (6)	0.0152 (2)
C11	0.17455 (17)	0.03233 (7)	0.02807 (6)	0.0177 (3)
H11	0.2946	0.0543	0.0472	0.021*
C12	0.16313 (17)	0.00478 (7)	−0.04609 (6)	0.0172 (3)
H12	0.2750	0.0083	−0.0774	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0305 (5)	0.0127 (4)	0.0254 (4)	0.0002 (3)	−0.0012 (4)	0.0010 (3)
O2	0.0239 (4)	0.0099 (4)	0.0138 (4)	−0.0011 (3)	−0.0001 (3)	−0.0015 (3)
C1	0.0278 (6)	0.0157 (5)	0.0176 (6)	−0.0019 (4)	−0.0012 (5)	0.0030 (4)
C2	0.0145 (5)	0.0141 (5)	0.0210 (6)	−0.0010 (4)	−0.0013 (4)	0.0016 (4)
C3	0.0131 (5)	0.0136 (5)	0.0171 (6)	0.0001 (4)	−0.0001 (4)	−0.0005 (4)
C4	0.0172 (5)	0.0133 (5)	0.0207 (6)	0.0000 (4)	−0.0002 (4)	−0.0032 (4)
C5	0.0186 (6)	0.0213 (6)	0.0162 (6)	−0.0008 (4)	−0.0001 (4)	−0.0056 (4)
C6	0.0174 (5)	0.0208 (6)	0.0150 (6)	−0.0007 (4)	0.0002 (4)	0.0019 (4)
C7	0.0165 (5)	0.0134 (5)	0.0182 (6)	−0.0001 (4)	−0.0005 (4)	0.0000 (4)
C8	0.0127 (5)	0.0147 (5)	0.0147 (5)	0.0003 (4)	−0.0004 (4)	−0.0022 (4)
C9	0.0229 (6)	0.0097 (5)	0.0159 (5)	0.0000 (4)	−0.0001 (4)	−0.0002 (4)
C10	0.0220 (6)	0.0082 (5)	0.0153 (5)	0.0018 (4)	−0.0010 (4)	−0.0005 (4)
C11	0.0177 (6)	0.0150 (5)	0.0204 (6)	−0.0019 (4)	−0.0020 (4)	−0.0019 (4)
C12	0.0191 (6)	0.0134 (5)	0.0193 (6)	−0.0001 (4)	0.0028 (4)	−0.0008 (4)

Geometric parameters (Å, º) top

O1—C2	1.2246 (13)	C6—C7	1.3846 (15)
O2—C8	1.3609 (13)	C6—H6	0.9500
O2—C9	1.4401 (12)	C7—C8	1.4002 (15)
C1—C2	1.5033 (15)	C7—H7	0.9500
C1—H1A	0.9800	C9—C10	1.5029 (15)
C1—H1B	0.9800	C9—H9A	0.9900
C1—H1C	0.9800	C9—H9B	0.9900
C2—C3	1.4970 (15)	C10—C12ⁱ	1.3907 (16)
C3—C4	1.3982 (15)	C10—C11	1.3912 (16)
C3—C8	1.4109 (15)	C11—C12	1.3897 (16)
C4—C5	1.3783 (16)	C11—H11	0.9500
C4—H4	0.9500	C12—C10ⁱ	1.3908 (16)
C5—C6	1.3892 (16)	C12—H12	0.9500
C5—H5	0.9500

C8—O2—C9	116.96 (8)	C6—C7—C8	120.24 (10)
C2—C1—H1A	109.5	C6—C7—H7	119.9
C2—C1—H1B	109.5	C8—C7—H7	119.9
H1A—C1—H1B	109.5	O2—C8—C7	122.38 (9)
C2—C1—H1C	109.5	O2—C8—C3	117.68 (9)
H1A—C1—H1C	109.5	C7—C8—C3	119.95 (9)
H1B—C1—H1C	109.5	O2—C9—C10	107.45 (8)
O1—C2—C3	119.09 (10)	O2—C9—H9A	110.2
O1—C2—C1	119.05 (10)	C10—C9—H9A	110.2
C3—C2—C1	121.86 (9)	O2—C9—H9B	110.2
C4—C3—C8	117.69 (10)	C10—C9—H9B	110.2
C4—C3—C2	116.40 (10)	H9A—C9—H9B	108.5
C8—C3—C2	125.90 (10)	C12ⁱ—C10—C11	119.34 (10)
C5—C4—C3	122.64 (10)	C12ⁱ—C10—C9	120.48 (10)
C5—C4—H4	118.7	C11—C10—C9	120.18 (10)
C3—C4—H4	118.7	C12—C11—C10	120.54 (11)
C4—C5—C6	118.80 (10)	C12—C11—H11	119.7
C4—C5—H5	120.6	C10—C11—H11	119.7
C6—C5—H5	120.6	C11—C12—C10ⁱ	120.12 (11)
C7—C6—C5	120.68 (10)	C11—C12—H12	119.9
C7—C6—H6	119.7	C10ⁱ—C12—H12	119.9
C5—C6—H6	119.7

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱⁱ	0.95	2.56	3.4649 (14)	158

Symmetry code: (ii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂O₄
M_r	374.42
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	6.8490 (1), 15.0815 (2), 17.8519 (3)
V (Å³)	1843.98 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.21 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.969, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	15454, 2013, 1728
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.100, 1.06
No. of reflections	2013
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

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

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.95	2.56	3.4649 (14)	158.3

Symmetry code: (i) −x, y−1/2, −z+1/2.

Acknowledgements

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

References

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 11| November 2011| Page o3016

doi:10.1107/S1600536811042528

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

1,1′-{2,2′-[1,4-Phenyl­enebis(methyl­ene)]bis­­(­­oxy)bis­­(2,1-phenyl­ene)}di­ethanone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,1′-{2,2′-[1,4-Phenylenebis(methylene)]bis(oxy)bis(2,1-phenylene)}diethanone