1,1′-{[1,4-Phenyl­enebis(methyl­ene)]bis­(­oxy)bis­(3,1-phenyl­ene)}diethanone

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

doi:10.1107/S1600536811045041

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3140

https://doi.org/10.1107/S1600536811045041

Open

access

1,1′-{[1,4-Phenylenebis(methylene)]bis(oxy)bis(3,1-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 24 October 2011; accepted 27 October 2011; online 2 November 2011)

In the title compound, C₂₄H₂₂O₄, the centroid of the central benzene ring lies on a special position of 2/m site symmetry, while the terminal aromatic rings are located on a mirror plane. The central and terminal benzene rings are perpendicular to each other. In the crystal, the molecules are connected via C—H⋯O hydrogen bonds into a three-dimensional polymeric structure. The network is further consolidated by a C—H⋯π interaction.

Related literature

For the related structure of the o-acetyl isomer, see: Al-Mohammed et al. (2011 ).

Experimental

Crystal data

C₂₄H₂₂O₄
M_r = 374.42
Monoclinic, C 2/m
a = 20.6446 (9) Å
b = 7.0205 (4) Å
c = 6.5523 (3) Å
β = 93.083 (3)°
V = 948.29 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.27 × 0.15 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.977, T_max = 0.996
3981 measured reflections
1120 independent reflections
872 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.05
1120 reflections
83 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the central benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2ⁱ	0.95	2.50	3.435 (2)	170
C11—H11⋯O1ⁱⁱ	0.95	2.54	3.4215 (16)	155
C6—H6⋯Cgⁱ	0.95	2.95	3.8469 (19)	157
Symmetry codes: (i) x, y, z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1]$ .

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/S1600536811045041/is2798sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045041/is2798Isup2.hkl

checkCIF report

Comment top

We have recently reported the crystal structure of the o-acetyl isomer of the title compound (Al-Mohammed et al., 2011). In the present molecule all the non-H atoms, except for C11, lie on a mirror plane and the centroid of the central benzene ring is placed on a special position of 2/m site symmetry. In the crystal, the molecules are linked through C—H···O bonds (Table 1) into a three-dimensional polymeric structure. The network is further consolidated by C—H···π interactions [C6 ···Cg = 3.8469 (19) Å where Cg is the centroid of the central benzene ring]

Related literature top

For the related structure of the o-acetyl isomer, see: Al-Mohammed et al. (2011).

Experimental top

To a mixture 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), 3'-hydroxyacetophenone (1.03 g, 7.57 mmole) was added. The mixture was refluxed for 2 days. 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 sodium sulfate. The solvent was then evaporated the solid was re-crystallized from chloroform to give off-white crystals of the title compound.

Structure description top

For the related structure of the o-acetyl isomer, see: Al-Mohammed et al. (2011).

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 codes: ' = -x+1, -y, -z; " = -x + 1, y, -z; "' = x, -y, z.]

1,1'-{[1,4-Phenylenebis(methylene)]bis(oxy)bis(3,1-phenylene)}diethanone top

Crystal data top

C₂₄H₂₂O₄	F(000) = 396
M_r = 374.42	D_x = 1.311 Mg m⁻³
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 1083 reflections
a = 20.6446 (9) Å	θ = 3.1–29.5°
b = 7.0205 (4) Å	µ = 0.09 mm⁻¹
c = 6.5523 (3) Å	T = 100 K
β = 93.083 (3)°	Plate, colorless
V = 948.29 (8) Å³	0.27 × 0.15 × 0.05 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	1120 independent reflections
Radiation source: fine-focus sealed tube	872 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 27.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→25
T_min = 0.977, T_max = 0.996	k = −8→8
3981 measured reflections	l = −8→8

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) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.045P)² + 0.5308P] where P = (F_o² + 2F_c²)/3
1120 reflections	(Δ/σ)_max < 0.001
83 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₄H₂₂O₄	V = 948.29 (8) Å³
M_r = 374.42	Z = 2
Monoclinic, C2/m	Mo Kα radiation
a = 20.6446 (9) Å	µ = 0.09 mm⁻¹
b = 7.0205 (4) Å	T = 100 K
c = 6.5523 (3) Å	0.27 × 0.15 × 0.05 mm
β = 93.083 (3)°

Data collection top

Bruker APEXII CCD diffractometer	1120 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	872 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.996	R_int = 0.024
3981 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
1120 reflections	Δρ_min = −0.21 e Å⁻³
83 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	Occ. (<1)
O1	0.09646 (6)	0.0000	0.6315 (2)	0.0420 (4)
O2	0.35997 (5)	0.0000	0.31330 (17)	0.0303 (4)
C1	0.11430 (9)	0.0000	0.2772 (3)	0.0379 (5)
H1A	0.1278	−0.1190	0.2140	0.057*	0.50
H1B	0.1340	0.1082	0.2090	0.057*	0.50
H1C	0.0669	0.0109	0.2635	0.057*	0.50
C2	0.13609 (9)	0.0000	0.5003 (3)	0.0305 (4)
C3	0.20700 (8)	0.0000	0.5583 (3)	0.0266 (4)
C4	0.22729 (9)	0.0000	0.7659 (3)	0.0366 (5)
H4	0.1961	0.0000	0.8674	0.044*
C5	0.29237 (9)	0.0000	0.8226 (3)	0.0383 (5)
H5	0.3058	0.0000	0.9636	0.046*
C6	0.33890 (8)	0.0000	0.6764 (3)	0.0294 (4)
H6	0.3838	0.0000	0.7170	0.035*
C7	0.31899 (8)	0.0000	0.4707 (2)	0.0255 (4)
C8	0.25302 (8)	0.0000	0.4124 (3)	0.0258 (4)
H8	0.2396	0.0000	0.2715	0.031*
C9	0.42832 (8)	0.0000	0.3689 (3)	0.0276 (4)
H9A	0.4399	−0.1144	0.4514	0.033*
C10	0.46469 (8)	0.0000	0.1763 (3)	0.0258 (4)
C11	0.48225 (6)	0.1701 (2)	0.08780 (18)	0.0310 (3)
H11	0.4701	0.2875	0.1468	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0241 (7)	0.0579 (10)	0.0452 (8)	0.000	0.0121 (6)	0.000
O2	0.0150 (6)	0.0586 (9)	0.0174 (6)	0.000	0.0014 (4)	0.000
C1	0.0199 (9)	0.0522 (14)	0.0409 (11)	0.000	−0.0038 (8)	0.000
C2	0.0220 (9)	0.0336 (11)	0.0365 (10)	0.000	0.0055 (7)	0.000
C3	0.0210 (9)	0.0340 (11)	0.0251 (9)	0.000	0.0029 (7)	0.000
C4	0.0280 (9)	0.0587 (14)	0.0239 (9)	0.000	0.0088 (7)	0.000
C5	0.0314 (10)	0.0656 (15)	0.0178 (8)	0.000	0.0029 (7)	0.000
C6	0.0210 (8)	0.0459 (12)	0.0211 (8)	0.000	−0.0008 (7)	0.000
C7	0.0220 (8)	0.0357 (11)	0.0189 (8)	0.000	0.0036 (6)	0.000
C8	0.0218 (8)	0.0355 (11)	0.0199 (8)	0.000	−0.0004 (6)	0.000
C9	0.0154 (8)	0.0466 (12)	0.0206 (8)	0.000	−0.0001 (6)	0.000
C10	0.0145 (8)	0.0429 (12)	0.0200 (8)	0.000	−0.0003 (6)	0.000
C11	0.0258 (6)	0.0401 (8)	0.0274 (7)	0.0016 (6)	0.0044 (5)	−0.0037 (6)

Geometric parameters (Å, º) top

O1—C2	1.218 (2)	C5—C6	1.393 (2)
O2—C7	1.3685 (19)	C5—H5	0.9500
O2—C9	1.4382 (19)	C6—C7	1.388 (2)
C1—C2	1.506 (3)	C6—H6	0.9500
C1—H1A	0.9800	C7—C8	1.394 (2)
C1—H1B	0.9800	C8—H8	0.9500
C1—H1C	0.9800	C9—C10	1.503 (2)
C2—C3	1.493 (2)	C9—H9A	0.9900
C3—C8	1.383 (2)	C10—C11	1.3844 (16)
C3—C4	1.402 (3)	C10—C11ⁱ	1.3844 (16)
C4—C5	1.375 (3)	C11—C11ⁱⁱ	1.397 (2)
C4—H4	0.9500	C11—H11	0.9500

C7—O2—C9	116.56 (12)	C7—C6—C5	119.27 (16)
C2—C1—H1A	109.5	C7—C6—H6	120.4
C2—C1—H1B	109.5	C5—C6—H6	120.4
H1A—C1—H1B	109.5	O2—C7—C6	124.68 (15)
C2—C1—H1C	109.5	O2—C7—C8	115.34 (14)
H1A—C1—H1C	109.5	C6—C7—C8	119.98 (15)
H1B—C1—H1C	109.5	C3—C8—C7	120.52 (15)
O1—C2—C3	120.47 (17)	C3—C8—H8	119.7
O1—C2—C1	120.54 (17)	C7—C8—H8	119.7
C3—C2—C1	118.99 (16)	O2—C9—C10	108.37 (13)
C8—C3—C4	119.34 (16)	O2—C9—H9A	110.0
C8—C3—C2	121.66 (16)	C10—C9—H9A	110.0
C4—C3—C2	119.00 (16)	C11—C10—C11ⁱ	119.26 (16)
C5—C4—C3	119.93 (17)	C11—C10—C9	120.36 (8)
C5—C4—H4	120.0	C11ⁱ—C10—C9	120.36 (8)
C3—C4—H4	120.0	C10—C11—C11ⁱⁱ	120.37 (8)
C4—C5—C6	120.95 (17)	C10—C11—H11	119.8
C4—C5—H5	119.5	C11ⁱⁱ—C11—H11	119.8
C6—C5—H5	119.5

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the central benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱⁱⁱ	0.95	2.50	3.435 (2)	170
C11—H11···O1^iv	0.95	2.54	3.4215 (16)	155
C6—H6···Cgⁱⁱⁱ	0.95	2.95	3.8469 (19)	157

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂O₄
M_r	374.42
Crystal system, space group	Monoclinic, C2/m
Temperature (K)	100
a, b, c (Å)	20.6446 (9), 7.0205 (4), 6.5523 (3)
β (°)	93.083 (3)
V (Å³)	948.29 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.27 × 0.15 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	3981, 1120, 872
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.05
No. of reflections	1120
No. of parameters	83
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −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

Cg is the centroid of the central benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.95	2.50	3.435 (2)	170
C11—H11···O1ⁱⁱ	0.95	2.54	3.4215 (16)	155
C6—H6···Cgⁱ	0.95	2.95	3.8469 (19)	157

Symmetry codes: (i) x, y, z+1; (ii) −x+1/2, y+1/2, −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
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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3140

https://doi.org/10.1107/S1600536811045041

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

1,1′-{[1,4-Phenyl­enebis(methyl­ene)]bis­­(­­oxy)bis­­(3,1-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(3,1-phenylene)}diethanone