Z. Kristallogr. NCS 2015; 230(4): 369–370
Open Access Meng Li, XueFeng Bai and YanJun Hou*
The crystal structure of 1-(2-(2-chloroethoxy) phenyl)ethanone Table 1: Data collection and handling. Crystal:
Colorless, block, size 0.26×0.26×0.28 mm Mo K α radiation (0.71073 Å) 3.49 cm−1 CCD area detector, φ and ω scans 56.66° 4158, 2375 Iobs > 2 σ(Iobs ), 2049 120 SHELXS97
Wavelength: µ: Diffractometer, scan mode: 2θmax : N(hkl)measured , N(hkl)unique : Criterion for Iobs , N(hkl)gt : N(param)refined : Programs:
Table 2: Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2 ). DOI 10.1515/ncrs-2015-0038 Received March 16, 2015; accepted October 2, 2015
Abstract ¯ (No. 2), a = 7.8470(3) Å, C10 H11 ClO2 triclinic, P1 b = 8.0375(3) Å, c = 9.2261(4) Å, α = 77.052(4)°, β = 86.981(5)°, γ = 61.011(4)°, V = 494.98(3) Å3 , Z = 4, Rgt (F) = 0.0441, wRref (F 2 ) = 0.1388, T = 296 K. CCDC no.: 1267/4367
Source of material 1-(2-(2-chloroethoxy)phenyl)ethanone is easily prepared by a literature synthesis method [1, 2]. To a solution of 2-Acetylphenol (50 mmol) in anhydrous 1,2-dichloroethane (50 mL) was added NaOH (70 mmol) in 30 mL water and 0.5 g tetrabutylammonium bromide. After heating the reaction mixture for 40 h under reflux, 100 mL water was added. The oil after separation was concentrated under reduced *Corresponding author: YanJun Hou, Key Laboratory of Chemical Engineering Process and Technology for High-Efficiency Conversion, College of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People’s Republic of China, e-mail:
[email protected] Meng Li and XueFeng Bai: School of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, People’s Republic of China
Atom
Site
H(1A) H(1B) H(1C) H(4) H(5) H(6) H(7) H(9A) H(9B) H(10A) H(10B)
2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i
x
y
z
Uiso
−0.1801 −0.2661 −0.4067 −0.2896 −0.0778 0.2042 0.277 0.3644 0.247 0.1179 0.2502
0.4711 0.3362 0.5542 0.5615 0.3758 0.0923 −0.0039 0.0073 −0.1093 0.0204 0.1199
0.2179 0.2003 0.2067 −0.2772 −0.4311 −0.3291 −0.0756 0.153 0.1775 0.392 0.3704
0.099 0.099 0.099 0.068 0.079 0.072 0.056 0.053 0.053 0.075 0.075
pressure and the residue was recrystallized from ethanol to give the title compound in a yield of 93%. Crystals suitable for single-crystal X-ray diffraction were obtained by evaporation from ethanol at room temperature.
Experimental details All H atoms on C atoms were placed in idealized positions [C—H = 0.96 (methyl), 0.97 (methylene) and 0.93 Å (aromatic)] and included in the refinement in the ridingmodel approximation, with U iso (H) = 1.5U eq (methyl C) and 1.2U eq (methylene and aromatic C).
Discussion The title compound have been widely is used as a synthetic intermediate for a number of chemical families of pharmaceuticals, pesticides, dyes, etc. [4–6]. Herein, we report the
© 2015 Meng Li et al., published by De Gruyter. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.
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370 | Li et al.: 1-(2-(2-chloroethoxy)phenyl)ethanone Table 3: Atomic displacement parameters (Å2 ). Atom
Site
C(1) C(2) C(3) C(4) C(5) C(6) C(7) C(8) C(9) C(10) Cl(1) O(1) O(2)
2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i
x
y
z
U11
U22
U33
U12
U13
U23
−0.2849(3) −0.2877(2) −0.1377(2) −0.1757(3) −0.0495(3) 0.1193(3) 0.1634(2) 0.0368(2) 0.2485(2) 0.2412(3) 0.43622(9) −0.4174(2) 0.0759(1)
0.4668(3) 0.5267(2) 0.3962(2) 0.4483(3) 0.3373(3) 0.1682(3) 0.1106(2) 0.2248(2) 0.0054(2) 0.0081(3) −0.20941(8) 0.6849(2) 0.1796(2)
0.1728(2) 0.0082(2) −0.0815(2) −0.2356(2) −0.3286(2) −0.2671(2) −0.1156(2) −0.0218(1) 0.1933(2) 0.3567(2) 0.46068(5) −0.0577(2) 0.1270(1)
0.0458(9) 0.0336(7) 0.0368(7) 0.0570(9) 0.082(1) 0.069(1) 0.0435(7) 0.0356(6) 0.0412(7) 0.070(1) 0.0963(5) 0.0496(7) 0.0415(5)
0.065(1) 0.0358(7) 0.0326(7) 0.0493(8) 0.081(1) 0.074(1) 0.0445(8) 0.0333(6) 0.0388(7) 0.056(1) 0.0763(4) 0.0404(6) 0.0416(5)
0.077(1) 0.080(1) 0.0497(8) 0.0548(9) 0.0381(8) 0.0434(8) 0.0442(7) 0.0383(6) 0.0395(7) 0.0433(8) 0.0510(3) 0.115(1) 0.0382(5)
−0.0130(8) −0.0133(5) −0.0160(5) −0.0269(7) −0.049(1) −0.0380(9) −0.0148(6) −0.0147(5) −0.0112(6) −0.0169(8) −0.0174(3) −0.0008(5) −0.0046(4)
0.0161(8) −0.0014(6) −0.0036(5) −0.0162(7) −0.0055(8) 0.0124(7) 0.0058(6) 0.0006(5) −0.0035(5) −0.0078(7) −0.0253(3) −0.0119(7) −0.0019(4)
−0.0319(9) −0.0151(7) −0.0026(5) 0.0098(7) 0.0021(8) −0.0183(8) −0.0121(6) −0.0054(5) −0.0026(5) −0.0080(7) 0.0053(2) −0.0113(7) −0.0091(4)
crystal structure of 1-(2-(2-chloroethoxy)phenyl)-ethanone. In the title crystal structure, the dihedral angle between the amide group and benzene ring is 11.81(2)°. The bond distances and bond angles are all in normal ranges. There is no classic Hydrogen bonds found. Some C—H. . .O hydrogen bonds may play a role in the stabilization of the structures.
Acknowledgements: We are grateful for financial support by the Education Department of Hei longjiang Province of China (No. 12521413).
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