Tetra­methyl 5,5′-[4,5-dicyano-1,2-phenyl­enebis(­oxy)]diisophthalate chloro­form monosolvate

Fei Yang; Fanjun Meng; Xiaomei Zhang; Ming Bai

doi:10.1107/S1600536811024718

. 2011 Jun 30;67(Pt 7):o1836. doi: 10.1107/S1600536811024718

Tetramethyl 5,5′-[4,5-dicyano-1,2-phenylenebis(oxy)]diisophthalate chloroform monosolvate

Fei Yang ^a, Fanjun Meng ^a, Xiaomei Zhang ^b, Ming Bai ^a,^*

PMCID: PMC3151808 PMID: 21837203

Abstract

In the title compound, C₂₈H₂₀N₂O₁₀·CHCl₃, the phenoxy rings are inclined to the central phenyl ring at dihedral angles of 84.71 (13) and 80.56 (13)°. In the crystal, pairs of weak intermolecular C—H⋯O hydrogen bonds link molecules related by an inversion center, forming dimers. There are also C—H⋯π interactions present.

Related literature

For general structural and background information on phthalocyanines, including properties and appplications, see: Kobayashi (2001 ▶); LukCentyanets (1999 ▶); Suda et al. (2009 ▶); Zhang et al. (2009 ▶). For the synthesis of the title compound, see: del Rey et al. (1998 ▶). For the crystal structure of a similar compound, dimethyl 2,2′-(4,5-dicyano-o-phenylenedioxy)dibenzoate, see: Ocak et al. (2004 ▶).

Experimental

Crystal data

C₂₈H₂₀N₂O₁₀·CHCl₃
M _r = 663.85
Triclinic,
a = 9.9223 (13) Å
b = 11.4374 (15) Å
c = 13.9398 (19) Å
α = 96.860 (2)°
β = 94.578 (2)°
γ = 105.326 (2)°
V = 1504.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 298 K
0.15 × 0.12 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
7568 measured reflections
5257 independent reflections
3557 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.159
S = 1.08
5257 reflections
397 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024718/su2272sup1.cif

e-67-o1836-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024718/su2272Isup2.hkl

e-67-o1836-Isup2.hkl^{(252.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024718/su2272Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O7ⁱ	0.93	2.60	3.455 (4)	154
C29—H29⋯O3ⁱⁱ	0.98	2.26	3.182 (5)	157
C19—H19A⋯Cg2ⁱⁱⁱ	0.98	2.90	3.709 (4)	143

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This work was supported by the Independent Innovation Foundation of Shandong University, IIFSDU.

supplementary crystallographic information

Comment

Dicyano compounds have been widely used to synthesize many useful materials such as phthalocyanines. Phthalocyanines are an interesting class of compounds, with increasingly diverse industrial and biomedical applications, for instance as dyes and pigments, materials for optical storage (Kobayashi et al. 2001), photodynamic therapy agents (LukCentyanets et al. 1999), catalysis (Suda et al. 2009), and corrosion inhibitors (Zhang et al. 2009). The title compound was prepared according to the method reported in the literature (del Rey et al., 1998), and its crystal structure is described herein. The crystal structure of a similar compound, Dimethyl 2,2'-(4,5-dicyano-o-phenylenedioxy)dibenzoate, has been described by (Ocak et al., 2004).

The molecular structure of the title compound is shown in Fig. 1. It has a kite-like configuration with the aromatic rings and two cyanide groups being the head and the substituted 3,5-Bismethoxycarbonyl phenoxy groups being the tails. The mean planes of the phenoxy rings [A = (C5-C10) and C = (C23-C28)] are inclinded to the mean plane of the central phenyl ring [B = (C11-C16)], with dihedral angles of A/B = 84.71 (13) ° and C/B = 80.56 (13) °, while planes A and C are inclined to one another by 11.93 (13) °.

In the crystal weak intermolecular C—H···O hydrogen bonds link molecules related by an inversion center to form dimers (Table 1). There is also a C-H···π interaction present in the crystal structure (Table 1).

Experimental

The title compound was prepared according to a published procedure (del Rey et al., 1998). Colourless block-like crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a solution of the title compound in chloroform.