8-Chloro­methyl-5-(2,5-dioxooxolan-3-yl)-3,3a,4,5-tetra­hydro-1H-naphtho­[1,2-c]furan-1,3-dione

Y Z Guo; Y Z Song; J G Liu; S Y Yang

doi:10.1107/S1600536813014943

. 2013 Jun 8;69(Pt 7):o1031–o1032. doi: 10.1107/S1600536813014943

8-Chloromethyl-5-(2,5-dioxooxolan-3-yl)-3,3a,4,5-tetrahydro-1H-naphtho[1,2-c]furan-1,3-dione

Y Z Guo ^a, Y Z Song ^b, J G Liu ^a,^*, S Y Yang ^a

PMCID: PMC3772467 PMID: 24046610

Abstract

The title compound, C₁₇H₁₃ClO₆, is an asymmetric alicyclic dianhydride containing a chloromethyl-substituted tetrahydronaphthalene moiety. The cyclohexene ring in the tetrahydronaphthalene moiety exhibits an envelope conformation with the tertiary C atom as the flap The dihedral angle between the two anhydride rings is 79.96 (6)°, while those between the benzene ring and the non-fused and fused anhydride rings are 71.03 (5) and 42.57 (7)°, respectively. In the crystal, molecules are connected by weak C—H⋯O interactions, forming a three-dimensional supramolecular structure.

Related literature

For background to polyimides, see: Li et al. (2005 ▶); Liaw et al. (2012 ▶); Zhang et al. (2003 ▶); Zhong et al. (2004 ▶). For background to and applications of tetrahydronaphthalene-containing alicyclic dianhydrides, see: Guo, Shen et al. (2013 ▶). For the structure of a related compound, see: Guo, Liu & Yang (2013 ▶) and for its synthesis, see: Hall et al. (1982 ▶); Guo et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₇H₁₃ClO₆
M _r = 348.72
Triclinic,
a = 6.8988 (15) Å
b = 9.140 (2) Å
c = 11.950 (3) Å
α = 80.937 (9)°
β = 75.365 (8)°
γ = 79.614 (8)°
V = 712.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 173 K
0.41 × 0.21 × 0.15 mm

Data collection

Rigaku Saturn724+ CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) ▶ T _min = 0.702, T _max = 1.000
9192 measured reflections
3238 independent reflections
3034 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.108
S = 1.10
3238 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008) ▶; cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014943/zp2004sup1.cif

e-69-o1031-sup1.cif^{(20KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014943/zp2004Isup2.hkl

e-69-o1031-Isup2.hkl^{(158.8KB, hkl)}

Click here for additional data file.^{(6.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813014943/zp2004Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O4ⁱ	0.99	2.51	3.420 (2)	153
C5—H5⋯O1ⁱⁱ	1.00	2.59	3.386 (2)	136
C7—H7⋯O4ⁱ	1.00	2.51	3.468 (2)	160

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

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China for financial support (grant No. 51173188).

supplementary crystallographic information

Comment

Polyimide (PI) is an important class of high performance polymers in the current industry. Functional PI materials have been widely used in microelectronic, optoelectronic and advanced display areas (Liaw et al., 2012). Chloromethyl is an important active species for functionalization of PI materials (Li et al., 2005). For instance, PIs which are highly sensitive to ultraviolet lights of high-pressure mercury lamps have been successfully developed via the reaction of chloromethyl substituted in the PI molecules with photosensitive substances, such as cinnamic acid (Zhang et al., 2003). In addition, chloromethyl-containing PIs exhibited good sensitivity to linearly polarized ultraviolet light, which making it possible using the PIs for the photoalignment fabrication of liquid crystal molecules in advanced liquid crystal display devices (Zhong et al., 2004). In the current work, we reported a novel chloromethyl-containing alicyclic dianhydride monomer. The molecular structure of the title compound is shown in Fig. 1. The compound has an asymmetrical structure and the dihedral angle between the two anhydride rings is 79.96 (6)° while the dihedral angles between the benzene ring and the anhydride ring 1(C1—C2—C3—C4—O2) and anhydride ring 2 (C7—C8—C9—C10—O5) are 71.03 (5)° and 42.57 (7)°, respectively. The six-membered cyclohexene ring in the tetra-hydronaphthalene residue exhibits an envelope conformation with puckering parameters of Q = 0.4805 (17) Å, θ=57.46 (19)° and φ =58.9 (2)°. =122.8 (2)° and φ=300.7 (2)° (Cremer & Pople, 1975). There is an intramolecular C—H···Cl hydrogen bond in the molecule, while in the crystal, molecules are connected by week C—H···O intermolecular interactions, as shown in Table 1.

Experimental

Into a 500 ml three-necked flask equipped with a mechanical stirrer, a nitric oxide inlet, and a condenser, 43.75 g(0.446 mol) of maleic anhydride, 104.09 g(0.682 mol) of 4-chloromethylstyrene, 0.1138 g(0.5 mmol) of 2,5-di-tert-butyl hydroquinone were added. The reaction mixture was heated to 120°C and maintained for 6 h under nitric oxide. The produced red-brown nitrogen oxide gas was trapped by passing through an aqueous solution of 20 wt% sodium hydroxide. White needle crystals were formed. After the reaction was completed, 60 ml of acetonitrile was added and the solution was refluxed for about 0.5 h. Then 60 ml of toluene was added and the reactino mixture was cooled to room temperature. The produced white needle crystals was collected by filtration and the solid was washed with toluene and petroleum ether in succession. After being dried in vacuum, the pure MCTDA was obtained as white crystals. Yield: 59.49 g(76.5%). Elemental analysis: calculated for C₁₇H₁₃ClO₆:C,58.55; H:3.76%. Found: C:58.71; H:3.85%. EI—MS, m/z:142(M⁺-176, 100%). Colourless single crystals were grown by slow evaporation of an acetonitrile solution over a period of several days.