Home Physical Sciences Crystal structure of diethyl 3,3′-(diazene-1,2-diyl)(E)-dibenzoate, C18H18N2O4
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Crystal structure of diethyl 3,3′-(diazene-1,2-diyl)(E)-dibenzoate, C18H18N2O4

  • Niu Yongsheng , Yu Youzhu EMAIL logo , Wei Aimin , Liu Nana and Wang Fengli
Published/Copyright: May 10, 2017

Abstract

C18H18N2O4, monoclinic, P21/n (no. 14), a = 5.2291(2) Å, b = 10.5932(4) Å, c = 15.3775(6) Å, β = 96.619(2)°, V = 846.13(6) Å3, Z = 4, Rgt(F) = 0.0479, wRref(F2) = 0.1438, T = 293(2) K.

CCDC no.:: 1545390

The molecular structure of the title compound is shown in the figure (’ = 2−x, 2−y, 2−z). Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Orange block
Size:0.20 × 0.20 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.9 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:57°, >99%
N(hkl)measured, N(hkl)unique, Rint:20762, 209, 0.022
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1866
N(param)refined:110
Programs:Bruker programs [1, 2] , SHELX [3], DIAMOND [4]
Table 2

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

AtomxyzUiso*/Ueq
O20.10504(18)0.65799(9)0.85455(6)0.0555(3)
C60.6243(2)0.86064(10)0.94331(7)0.0418(3)
H60.62320.92080.89920.050*
C10.8062(2)0.86682(11)1.01687(7)0.0419(3)
C50.4449(2)0.76376(10)0.93660(7)0.0405(3)
C40.4443(2)0.67457(12)1.00307(8)0.0498(3)
H40.32220.61040.99860.060*
O10.2532(2)0.83270(11)0.79680(7)0.0799(4)
C20.8067(3)0.77771(13)1.08252(8)0.0538(3)
H20.92890.78221.13140.065*
C70.2592(2)0.75768(11)0.85532(8)0.0468(3)
C30.6257(3)0.68168(13)1.07583(9)0.0606(4)
H30.62620.62201.12020.073*
C8−0.0801(3)0.64201(16)0.77739(9)0.0657(4)
H8A0.00840.63030.72590.079*
H8B−0.18910.71610.76850.079*
C9−0.2372(3)0.52945(14)0.79195(11)0.0662(4)
H9A−0.12910.45600.79690.099*
H9B−0.36870.51930.74350.099*
H9C−0.31590.54010.84490.099*
N11.00062(18)0.96177(9)1.03032(6)0.0463(3)

Source of material

All reagents and solvents were commercially available and used as received without further purification. Azobenzene-3,3′-dicarbonylchloride (3 mmol) was added to a solution of ethanol (25 mL) and 1,2-dichloroethane (15 mL). The reaction mixture was stirred at 80 °C for 3 h, then the solution was naturally cooled to room temperature. After filtration orange flakes of the title compound were obtained with 94.6% yield. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution including 0.05 g of the product in methanol (5 mL) and chloroform (5 mL).

Experimental details

H atoms were subsequently treated as riding atoms with distances C—H = 0.96 (CH3), 0.97 (CH2), 0.93 Å (ArH) and O—H = 0.85 Å.

Comment

In recent years, the study of liquid crystalline materials has been of interest due to their potentially wide range of applications, such as in electrical [5], optical [6], and biological medical fields [7]. In this respect, the preparation of liquid crystalline materials containing azobenzene moieties appears to be very promising, because the photoinduced trans-cis isomerization of azobenzene chromophores can give rise to photochromic and optical dichroic effects [8]. Liquid crystalline polymers containing azobenzene derivatives have been widely investigated for the photo-controlled release of drugs [9], the preparation of holographic optical memories [10], and non-linear optical materials [11]. In order to enlarge the number of azobenzene derivatives, the synthesis and crystal structure of the title compound was investigated.

The title crystal structure is centrosymmetric and contains one half of a title molecule in the asymmetric unit. Consequently the title molecule is located around an inversion center in the monoclinic space group P21/n (cf. the figure). Thus the intersection angle between two aryl rings is 0°, which is the same to that of azobenzene [12]. The crystal packing does not exhibit classical hydrogen bond interactions.

Acknowledgement

This work was supported by the Foundation of Anyang Institute of Technology.

References

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Received: 2016-11-22
Accepted: 2017-4-25
Published Online: 2017-5-10
Published in Print: 2017-7-26

©2017 Niu Yongsheng et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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