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The crystal structure of 1-(2-(2-chloroethoxy)phenyl)ethanone

  • Meng Li , XueFeng Bai and YanJun Hou EMAIL logo
Published/Copyright: December 7, 2015
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 230 Issue 4

Abstract

C10H11ClO2 triclinic, P1̅ (No. 2), a = 7.8470(3) Å, 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(F2) = 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 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.

Table 1

Data collection and handling.

Crystal:Colorless, block, size 0.26×0.26×0.28 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:3.49 cm−1
Diffractometer, scan mode:CCD area detector, φ and ω scans
2θmax:56.66°
N(hkl)measured, N(hkl)unique:4158, 2375
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2049
N(param)refined:120
Programs:SHELXS97
Table 2

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

AtomSitexyzUiso
H(1A)2i−0.18010.47110.21790.099
H(1B)2i−0.26610.33620.20030.099
H(1C)2i−0.40670.55420.20670.099
H(4)2i−0.28960.5615−0.27720.068
H(5)2i−0.07780.3758−0.43110.079
H(6)2i0.20420.0923−0.32910.072
H(7)2i0.277−0.0039−0.07560.056
H(9A)2i0.36440.00730.1530.053
H(9B)2i0.247−0.10930.17750.053
H(10A)2i0.11790.02040.3920.075
H(10B)2i0.25020.11990.37040.075
Table 3

Atomic displacement parameters (Å2).

AtomSitexyzU11U22U33U12U13U23
C(1)2i−0.2849(3)0.4668(3)0.1728(2)0.0458(9)0.065(1)0.077(1)−0.0130(8)0.0161(8)−0.0319(9)
C(2)2i−0.2877(2)0.5267(2)0.0082(2)0.0336(7)0.0358(7)0.080(1)−0.0133(5)−0.0014(6)−0.0151(7)
C(3)2i−0.1377(2)0.3962(2)−0.0815(2)0.0368(7)0.0326(7)0.0497(8)−0.0160(5)−0.0036(5)−0.0026(5)
C(4)2i−0.1757(3)0.4483(3)−0.2356(2)0.0570(9)0.0493(8)0.0548(9)−0.0269(7)−0.0162(7)0.0098(7)
C(5)2i−0.0495(3)0.3373(3)−0.3286(2)0.082(1)0.081(1)0.0381(8)−0.049(1)−0.0055(8)0.0021(8)
C(6)2i0.1193(3)0.1682(3)−0.2671(2)0.069(1)0.074(1)0.0434(8)−0.0380(9)0.0124(7)−0.0183(8)
C(7)2i0.1634(2)0.1106(2)−0.1156(2)0.0435(7)0.0445(8)0.0442(7)−0.0148(6)0.0058(6)−0.0121(6)
C(8)2i0.0368(2)0.2248(2)−0.0218(1)0.0356(6)0.0333(6)0.0383(6)−0.0147(5)0.0006(5)−0.0054(5)
C(9)2i0.2485(2)0.0054(2)0.1933(2)0.0412(7)0.0388(7)0.0395(7)−0.0112(6)−0.0035(5)−0.0026(5)
C(10)2i0.2412(3)0.0081(3)0.3567(2)0.070(1)0.056(1)0.0433(8)−0.0169(8)−0.0078(7)−0.0080(7)
Cl(1)2i0.43622(9)−0.20941(8)0.46068(5)0.0963(5)0.0763(4)0.0510(3)−0.0174(3)−0.0253(3)0.0053(2)
O(1)2i−0.4174(2)0.6849(2)−0.0577(2)0.0496(7)0.0404(6)0.115(1)−0.0008(5)−0.0119(7)−0.0113(7)
O(2)2i0.0759(1)0.1796(2)0.1270(1)0.0415(5)0.0416(5)0.0382(5)−0.0046(4)−0.0019(4)−0.0091(4)

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 riding-model approximation, with Uiso(H) = 1.5Ueq(methyl C) and 1.2Ueq(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 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.

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:

Acknowledgements:

We are grateful for financial support by the Education Department of Hei longjiang Province of China (No. 12521413).

References

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3. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

4. Bali, A.; Sharma, K.; Bhalla, A.; Bala, S.; Reddy, D.; Singh, A.; Kumar, A.: Synthesis, evaluation and computational studies on a series of acetophenone based 1-(aryloxypropyl)-4-(chloroaryl) piperazines as potential atypical antipsychotics, Eur. J. Med. Chem. 45 (2010) 2656–2662.Search in Google Scholar

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Received: 2015-3-16
Accepted: 2015-10-2
Published Online: 2015-12-7
Published in Print: 2015-12-1

©2015 Meng Li et al., published by De Gruyter.

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

Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidozincate(II), C40H40Br4P2Zn
  3. Crystal structure of chlorido-(2-ethoxy-6-(((quinolin-8-yl)methyl)-phenolato-κ3N,N′,O)-copper(II), C18H15ClCuN2O2
  4. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidocobaltate(II), C40H40Br4CoP2
  5. Crystal structure of di(pyrrolidin-1-yl)methane-thione, C9H16N2S
  6. Crystal structure of ammonium phenylglyoxylate, C8H9NO3
  7. Crystal structure of 2-hydroxy-2-methyl-2-phenyl acetic acid hemihydrate, C9H11O3.50
  8. Crystal structure of 2-((E)-2-(1H-benzo[d]imidazol-2-yl)vinyl)-1H-benzo[d]imidazolium dichloride dihydrate, C16H18Cl2N4O2
  9. Crystal structure of 1,2-dimethylimidazolium iodide, C5H9IN2
  10. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraqua-cobalt(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34CoN2O14
  11. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-bis(thiophene-3,4-dicarboxylato-κ2O,O′)-cadmium(II), C32H22CdN4O8S2
  12. Crystal structure of tetraaqua-(4,4′-diamino-1,1′-biphenyl-2,2′-disulfonato-κN)(4,4′-bipyridyl-κN)zinc(II) trihydrate, C22H32N4O13S2Zn
  13. Crystal structure of poly[[[(1,3-dimethyl-2-imidazolidinone-κ1O11) zinc(II)]-μ-1,4-benzenedi-carboxylato-κ4O1,O2:O3,O4]—1,3-dimethyl-2-imidazolidinone (1:1)], [Zn(C5H10N2O)(C8H4O4)]· C5H10N2O, C18H24N4O6Zn
  14. Crystal structure of poly[[(1,3-dimethyl-2-imidazolidinone-κ1O) zinc(II)]-μ-furan-2,5-dicarboxylato-κ4O,O′:O′′,O′′′], [Zn(C5H10N2O)(C6H2O5)], C22H24N4O12Zn2
  15. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraquamanganese(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34MnN2O14
  16. Crystal structure of chlorido-tricarbonyl-bis(2-pyridylmethanone-N,N′)-rhenium(I), C14H8ClN2O4Re
  17. Crystal structure of (2-(benzoyl)phenolato-κ2O,O′)-trans-dichlorido -cis- bis(methoxido) niobium(V), C15H15Cl2NbO4
  18. Crystal structure of potassium diaqua dihydroxy(methylenediphosphonato-κ2-O,O′)cobaltate(III), CH10CoKO10P2
  19. Crystal structure of hexakis(4-(dimethylamino)pyridin-1-ium) decavanadate-water (1:16), C42H98N12O44V10
  20. Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2
  21. Crystal structure of bis[μ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κ2N:N′]bis[dibromido]dimercury(II), C24H26Br4Hg2N10
  22. Crystal structure of poly{bis-[(4,4′-biphenyl-dicarboxylate-κ2O:O′)-μ-1,1′-oxy-bis-(ethane-2,1-diyl)-bis-(1H-imidazole)-κ2N:N′] zinc(II)}dihydrate, C48H48N8O12Zn2
  23. Crystal structure of sodium poly[(μ4-2,2′,2′′-nitrilotriacetato-κ4O,O′,O′′,N)magnesium(II)] monohydrate
  24. The crystal structure of 1-(2-(2-chloroethoxy)phenyl)ethanone
  25. The crystal structure of tris(μ2-1,3-bis(4,4,4-Trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-/κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-O,O′)-diterbium(III)
  26. Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3
  27. Crystal structure of cis-tetrachloridobis-(pyridine-κN)platinum(IV), C10H10Cl4N2Pt
  28. Crystal structure of catena-poly[aqua-(μ2-5-norbornene-2,3-dicarboxylato-κ3O,O′:O′′)-(1,10-phenanthroline-κ2N,N′)zinc(II)], [Zn(C9H8O4)(C12H8N2)(H2O)]n
https://doi.org/10.1515/ncrs-2015-0038
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidozincate(II), C40H40Br4P2Zn
  3. Crystal structure of chlorido-(2-ethoxy-6-(((quinolin-8-yl)methyl)-phenolato-κ3N,N′,O)-copper(II), C18H15ClCuN2O2
  4. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidocobaltate(II), C40H40Br4CoP2
  5. Crystal structure of di(pyrrolidin-1-yl)methane-thione, C9H16N2S
  6. Crystal structure of ammonium phenylglyoxylate, C8H9NO3
  7. Crystal structure of 2-hydroxy-2-methyl-2-phenyl acetic acid hemihydrate, C9H11O3.50
  8. Crystal structure of 2-((E)-2-(1H-benzo[d]imidazol-2-yl)vinyl)-1H-benzo[d]imidazolium dichloride dihydrate, C16H18Cl2N4O2
  9. Crystal structure of 1,2-dimethylimidazolium iodide, C5H9IN2
  10. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraqua-cobalt(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34CoN2O14
  11. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-bis(thiophene-3,4-dicarboxylato-κ2O,O′)-cadmium(II), C32H22CdN4O8S2
  12. Crystal structure of tetraaqua-(4,4′-diamino-1,1′-biphenyl-2,2′-disulfonato-κN)(4,4′-bipyridyl-κN)zinc(II) trihydrate, C22H32N4O13S2Zn
  13. Crystal structure of poly[[[(1,3-dimethyl-2-imidazolidinone-κ1O11) zinc(II)]-μ-1,4-benzenedi-carboxylato-κ4O1,O2:O3,O4]—1,3-dimethyl-2-imidazolidinone (1:1)], [Zn(C5H10N2O)(C8H4O4)]· C5H10N2O, C18H24N4O6Zn
  14. Crystal structure of poly[[(1,3-dimethyl-2-imidazolidinone-κ1O) zinc(II)]-μ-furan-2,5-dicarboxylato-κ4O,O′:O′′,O′′′], [Zn(C5H10N2O)(C6H2O5)], C22H24N4O12Zn2
  15. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraquamanganese(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34MnN2O14
  16. Crystal structure of chlorido-tricarbonyl-bis(2-pyridylmethanone-N,N′)-rhenium(I), C14H8ClN2O4Re
  17. Crystal structure of (2-(benzoyl)phenolato-κ2O,O′)-trans-dichlorido -cis- bis(methoxido) niobium(V), C15H15Cl2NbO4
  18. Crystal structure of potassium diaqua dihydroxy(methylenediphosphonato-κ2-O,O′)cobaltate(III), CH10CoKO10P2
  19. Crystal structure of hexakis(4-(dimethylamino)pyridin-1-ium) decavanadate-water (1:16), C42H98N12O44V10
  20. Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2
  21. Crystal structure of bis[μ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κ2N:N′]bis[dibromido]dimercury(II), C24H26Br4Hg2N10
  22. Crystal structure of poly{bis-[(4,4′-biphenyl-dicarboxylate-κ2O:O′)-μ-1,1′-oxy-bis-(ethane-2,1-diyl)-bis-(1H-imidazole)-κ2N:N′] zinc(II)}dihydrate, C48H48N8O12Zn2
  23. Crystal structure of sodium poly[(μ4-2,2′,2′′-nitrilotriacetato-κ4O,O′,O′′,N)magnesium(II)] monohydrate
  24. The crystal structure of 1-(2-(2-chloroethoxy)phenyl)ethanone
  25. The crystal structure of tris(μ2-1,3-bis(4,4,4-Trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-/κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-O,O′)-diterbium(III)
  26. Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3
  27. Crystal structure of cis-tetrachloridobis-(pyridine-κN)platinum(IV), C10H10Cl4N2Pt
  28. Crystal structure of catena-poly[aqua-(μ2-5-norbornene-2,3-dicarboxylato-κ3O,O′:O′′)-(1,10-phenanthroline-κ2N,N′)zinc(II)], [Zn(C9H8O4)(C12H8N2)(H2O)]n
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