organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

5-Chloro-1-phenyl­pentan-1-one

aInstitut für Radiopharmazeutische Krebsforschung, Helmholtz-Zentrum Dresden-Rossendorf e.V., Postfach 51 01 19, D-01314 Dresden, Germany, bDepartment of Chemistry and Food Chemistry, Technische Universität Dresden, D-01062 Dresden, Germany, and cUniversität Rostock, Institut für Chemie, Anorganische Festkörperchemie, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany
*Correspondence e-mail: martin.koeckerling@uni-rostock.de

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 29 December 2015; accepted 11 January 2016; online 23 January 2016)

In the title compound, C11H13ClO, which is used as a starting material for the synthesis of some materials with possible medical applications, the mol­ecular skeleton is slightly curved, with the dihedral angle of 4.7 (1)° between the mean planes of the chloro­butane and benzaldehyde fragments. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains running along the [201] direction, and weak C—H⋯π inter­actions link these chains into layers parallel to the ac plane.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The synthesis of the title compound, (I), was previously described in the preparation of building blocks for the synthesis of ω-phenyl­alkyl­pyrimidines and purines (Komissarov et al. 2010[Komissarov, V. V. & Kritzyn, A. M. (2010). Russ. J. Bioorg. Chem. 36, 477-487.]; Gromov et al. 1999[Gromov, M. Y., Skachilova, S. Y., Aleksandrova, E. V. & Kochergin, P. M. (1999). Chem. Heterocycl. Compd. 35, 1225-1229.]). Another application is the use as coupling component for the synthesis of acyclic triaryl olefins, which were described as selective cyclo­oxygenase-2 inhibitors (Abdellatif et al., 2010[Abdellatif, K. R., Velázquez, C. A., Huang, Z., Chowdhury, M. A. & Knaus, E. E. (2010). Bioorg. Med. Chem. Lett. 20, 5245-5250.], 2011[Abdellatif, K. R., Velázquez, C. A., Huang, Z., Chowdhury, M. A. & Knaus, E. E. (2011). Bioorg. Med. Chem. Lett. 21, 1195-1198.]; Uddin et al. 2004a[Uddin, M. J., Rao, P. N. P. & Knaus, E. E. (2004a). Bioorg. Med. Chem. 12, 5929-5940.],b[Uddin, M. J., Rao, P. N. P. & Knaus, E. E. (2004b). Bioorg. Med. Chem. Lett. 14, 1953-1956.]) and selective estrogen receptor modulators (Chen et al., 2012[Chen, X. Y., Park, S. J., Buschmann, H., De Rosa, M. & Bolm, C. (2012). Bioorg. Med. Chem. Lett. 22, 4307-4309.]; Shiina et al. 2007[Shiina, I., Sano, Y., Nakata, K., Suzuki, M., Yokoyama, T., Sasaki, A., Orikasa, T., Miyamoto, T., Ikekita, M., Nagahara, Y. & Hasome, Y. (2007). Bioorg. Med. Chem. 15, 7599-7617.]). In our study, (I) was obtained as product of the reaction of 5-chloro­valeryl chloride with benzene in the presence of aluminium chloride via Friedel–Crafts acyl­ation.

The mol­ecule of (I) (Fig. 1[link]) is nearly flat, but not completely planar - the two mean planes formed by the chloro­butane (Cl1/C1–C4) fragment and by the rest of non-H atoms, respectively, are inclined to each other by 4.7 (1)°. In the crystal, weak C—H⋯O hydrogen bonds (Table 1[link]) link the mol­ecules into chains running along [201]. Weak C—H⋯π inter­actions (Table 1[link]) link these chains into layers parallel to the ac plane. Van der Waals forces stabilize further the crystal packing (Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C6–C11 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11⋯O1i 0.95 2.51 3.422 (2) 169
C2—H2ACgii 0.99 2.80 3.676 (2) 148
Symmetry codes: (i) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].
[Figure 1]
Figure 1
The mol­ecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2]
Figure 2
A portion of the crystal packing, viewed approximately along the a axis.

Synthesis and crystallization

To an ice-cold suspension of aluminium chloride (1.76 g, 13.23 mmol) in 10 ml chloro­form, 1.86 ml 5-chloro­valeryl chloride (14.40 mmol) and 0.99 ml benzene (11.54 mmol) were added under an argon atmosphere. After stirring for 1.5 h at room temperature, the reaction mixture was poured into a mixture of ice and water (15 ml). The organic layer was separated and washed three times with water (10 ml). The separated aqueous solution was extracted three times with CHCl3 (15 ml), the combined organic layer was dried over Na2SO4 and the solvent was removed under vacuum. After purification with semi-preparative HPLC (ProStar; Varian; microsorb 60, C18; water/aceto­nitrile + 0.1% TFA; 35 min: 5/5, v/v; 7 ml min−1). 5-Chloro-1-phenyl­pentan-1-one was obtained as a yellow solid in 91.6% yield. Colorless crystals were obtained by crystallization from aceto­nitrile/water + 0.1% TFA after chromatographic separation.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C11H13ClO
Mr 196.66
Crystal system, space group Monoclinic, P21/c
Temperature (K) 173
a, b, c (Å) 5.2434 (4), 25.902 (2), 7.7027 (6)
β (°) 104.756 (5)
V3) 1011.6 (1)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.33
Crystal size (mm) 0.32 × 0.27 × 0.26
 
Data collection
Diffractometer Bruker APEXII CCD diffractometer
Absorption correction Multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
No. of measured, independent and observed [I > 2σ(I)] reflections 9116, 2343, 1411
Rint 0.042
(sin θ/λ)max−1) 0.652
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.108, 1.01
No. of reflections 2343
No. of parameters 119
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.22, −0.31
Computer programs: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2007[Bruker (2007). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Comment top

The synthesis of the title compound, (I), was previously described in the preparation of building blocks for the synthesis of ω-phenylalkylpyrimidines and purines (Komissarov et al. 2010; Gromov et al. 1999). Another application is the use as coupling component for the synthesis of acyclic triaryl olefins, which were described as selective cyclooxygenase-2 inhibitors (Abdellatif et al., 2010, 2011; Uddin et al. 2004a,b) and selective estrogen receptor modulators (Chen et al., 2012; Shiina et al. 2007). In our study, (I) was obtained as product of the reaction of 5-chlorovaleryl chloride with benzene in the presence of aluminium chloride via Friedel-Crafts acylation.

The molecule of (I) (Fig. 1) is nearly flat, but not completely planar - two mean planes formed by the chlorobutane (Cl1/C1—C4) fragment and by the rest of non-H atoms, respectively, are inclined to each other at 4.7 (1)%. In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains running in [201], and weak C—H···π interactions (Table 1) link these chains into layers parallel to the ac plane. Van der Waals forces stabilize further the crystal packing (Fig. 2).

Experimental top

To an ice-cold suspension of aluminium chloride (1.76 g, 13.23 mmol) in 10 ml chloroform, 1.86 ml 5-chlorovaleryl chloride (14.40 mmol) and 0.99 ml benzene (11.54 mmol) were added under an argon atmosphere. After stirring for 1.5 h at room temperature, the reaction mixture was poured into a mixture of ice and water (15 ml). The organic layer was separated and washed three times with water (10 ml). The separated aqueous solution was extracted three times with CHCl3 (15 ml), the combined organic layer was dried over Na2SO4 and the solvent was removed under vacuum. After purification with semi-preparative HPLC (ProStar; Varian; microsorb 60, C18; water/acetonitrile + 0.1% TFA; 35 min: 5/5, v/v; 7 ml min−1) 5-chloro-1-phenylpentan-1-one was obtained as a yellow solid in 91.6% yield. Colorless crystals were obtained by crystallization from acetonitrile/water + 0.1% TFA after chromatographic separation.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2.

Structure description top

The synthesis of the title compound, (I), was previously described in the preparation of building blocks for the synthesis of ω-phenylalkylpyrimidines and purines (Komissarov et al. 2010; Gromov et al. 1999). Another application is the use as coupling component for the synthesis of acyclic triaryl olefins, which were described as selective cyclooxygenase-2 inhibitors (Abdellatif et al., 2010, 2011; Uddin et al. 2004a,b) and selective estrogen receptor modulators (Chen et al., 2012; Shiina et al. 2007). In our study, (I) was obtained as product of the reaction of 5-chlorovaleryl chloride with benzene in the presence of aluminium chloride via Friedel–Crafts acylation.

The molecule of (I) (Fig. 1) is nearly flat, but not completely planar - two mean planes formed by the chlorobutane (Cl1/C1–C4) fragment and by the rest of non-H atoms, respectively, are inclined to each other by 4.7 (1)°. In the crystal, weak C—H···O hydrogen bonds (Table 1) link the molecules into chains running along [201]. Weak C—H···π interactions (Table 1) link these chains into layers parallel to the ac plane. van der Waals forces stabilize further the crystal packing (Fig. 2).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. A portion of the crystal packing, viewed approximately along the a axis.
5-Chloro-1-phenylpentan-1-one top
Crystal data top
C11H13ClODx = 1.291 Mg m3
Mr = 196.66Melting point = 320–321 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.2434 (4) ÅCell parameters from 1422 reflections
b = 25.902 (2) Åθ = 2.9–22.7°
c = 7.7027 (6) ŵ = 0.33 mm1
β = 104.756 (5)°T = 173 K
V = 1011.6 (1) Å3Irregular block, colorless
Z = 40.32 × 0.27 × 0.26 mm
F(000) = 416
Data collection top
Bruker APEXII CCD
diffractometer
2343 independent reflections
Radiation source: sealed tube1411 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 65
k = 3329
9116 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0362P)2 + 0.2948P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2343 reflectionsΔρmax = 0.22 e Å3
119 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0021 (13)
Crystal data top
C11H13ClOV = 1011.6 (1) Å3
Mr = 196.66Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.2434 (4) ŵ = 0.33 mm1
b = 25.902 (2) ÅT = 173 K
c = 7.7027 (6) Å0.32 × 0.27 × 0.26 mm
β = 104.756 (5)°
Data collection top
Bruker APEXII CCD
diffractometer
2343 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
1411 reflections with I > 2σ(I)
Rint = 0.042
9116 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.01Δρmax = 0.22 e Å3
2343 reflectionsΔρmin = 0.31 e Å3
119 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.30681 (13)0.47935 (2)0.72353 (9)0.0622 (2)
C10.0779 (4)0.42960 (8)0.6269 (3)0.0403 (5)
H1A0.08130.43260.67310.048*
H1B0.02310.43400.49490.048*
C20.1990 (4)0.37676 (7)0.6714 (2)0.0330 (5)
H2A0.25070.37220.80330.040*
H2B0.36020.37410.62740.040*
C30.0082 (4)0.33416 (8)0.5870 (2)0.0335 (5)
H3A0.04850.33950.45550.040*
H3B0.15030.33600.63420.040*
C40.1323 (4)0.28088 (7)0.6257 (2)0.0311 (5)
H4A0.28690.27880.57440.037*
H4B0.19610.27630.75730.037*
C50.0547 (4)0.23775 (8)0.5504 (2)0.0322 (5)
O10.2751 (3)0.24672 (6)0.4561 (2)0.0515 (4)
C60.0313 (4)0.18322 (8)0.5912 (2)0.0286 (4)
C70.1480 (4)0.14405 (8)0.5232 (2)0.0342 (5)
H70.31850.15270.45140.041*
C80.0816 (4)0.09289 (8)0.5587 (3)0.0395 (5)
H80.20660.06650.51280.047*
C90.1679 (4)0.07998 (8)0.6614 (3)0.0386 (5)
H90.21430.04480.68550.046*
C100.3486 (4)0.11831 (8)0.7284 (3)0.0352 (5)
H100.51960.10930.79830.042*
C110.2830 (4)0.16993 (8)0.6946 (2)0.0307 (5)
H110.40850.19610.74160.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0628 (5)0.0355 (4)0.0776 (5)0.0012 (3)0.0018 (3)0.0025 (3)
C10.0395 (12)0.0400 (13)0.0373 (11)0.0058 (10)0.0023 (9)0.0023 (9)
C20.0318 (11)0.0358 (12)0.0297 (10)0.0081 (9)0.0044 (8)0.0026 (9)
C30.0306 (11)0.0396 (12)0.0283 (10)0.0074 (9)0.0040 (8)0.0010 (9)
C40.0279 (10)0.0366 (12)0.0276 (9)0.0028 (9)0.0045 (8)0.0003 (8)
C50.0270 (11)0.0430 (13)0.0257 (10)0.0004 (9)0.0049 (8)0.0009 (9)
O10.0338 (9)0.0503 (10)0.0572 (10)0.0034 (8)0.0125 (7)0.0044 (8)
C60.0267 (10)0.0379 (12)0.0214 (9)0.0013 (9)0.0064 (8)0.0006 (8)
C70.0283 (11)0.0438 (13)0.0294 (10)0.0034 (10)0.0051 (8)0.0007 (9)
C80.0358 (12)0.0437 (14)0.0397 (11)0.0112 (10)0.0106 (10)0.0052 (10)
C90.0423 (13)0.0343 (13)0.0418 (12)0.0003 (10)0.0153 (10)0.0009 (10)
C100.0306 (11)0.0391 (13)0.0354 (11)0.0046 (10)0.0076 (9)0.0020 (9)
C110.0248 (10)0.0371 (12)0.0287 (10)0.0013 (9)0.0042 (8)0.0021 (8)
Geometric parameters (Å, º) top
Cl1—C11.789 (2)C5—O11.221 (2)
C1—C21.511 (3)C5—C61.491 (3)
C1—H1A0.9900C6—C71.392 (3)
C1—H1B0.9900C6—C111.400 (2)
C2—C31.520 (3)C7—C81.380 (3)
C2—H2A0.9900C7—H70.9500
C2—H2B0.9900C8—C91.386 (3)
C3—C41.522 (3)C8—H80.9500
C3—H3A0.9900C9—C101.379 (3)
C3—H3B0.9900C9—H90.9500
C4—C51.502 (3)C10—C111.389 (3)
C4—H4A0.9900C10—H100.9500
C4—H4B0.9900C11—H110.9500
C2—C1—Cl1111.07 (14)H4A—C4—H4B107.7
C2—C1—H1A109.4O1—C5—C6119.69 (18)
Cl1—C1—H1A109.4O1—C5—C4120.95 (19)
C2—C1—H1B109.4C6—C5—C4119.36 (16)
Cl1—C1—H1B109.4C7—C6—C11118.92 (18)
H1A—C1—H1B108.0C7—C6—C5118.17 (17)
C1—C2—C3111.59 (16)C11—C6—C5122.92 (17)
C1—C2—H2A109.3C8—C7—C6120.89 (18)
C3—C2—H2A109.3C8—C7—H7119.6
C1—C2—H2B109.3C6—C7—H7119.6
C3—C2—H2B109.3C7—C8—C9119.90 (19)
H2A—C2—H2B108.0C7—C8—H8120.0
C2—C3—C4111.86 (15)C9—C8—H8120.0
C2—C3—H3A109.2C10—C9—C8119.9 (2)
C4—C3—H3A109.2C10—C9—H9120.0
C2—C3—H3B109.2C8—C9—H9120.0
C4—C3—H3B109.2C9—C10—C11120.62 (19)
H3A—C3—H3B107.9C9—C10—H10119.7
C5—C4—C3113.21 (15)C11—C10—H10119.7
C5—C4—H4A108.9C10—C11—C6119.74 (18)
C3—C4—H4A108.9C10—C11—H11120.1
C5—C4—H4B108.9C6—C11—H11120.1
C3—C4—H4B108.9
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C6–C11 benzene ring.
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.952.513.422 (2)169
C2—H2A···Cgii0.992.803.676 (2)148
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C6–C11 benzene ring.
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.952.513.422 (2)169
C2—H2A···Cgii0.992.803.676 (2)148
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H13ClO
Mr196.66
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)5.2434 (4), 25.902 (2), 7.7027 (6)
β (°) 104.756 (5)
V3)1011.6 (1)
Z4
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.32 × 0.27 × 0.26
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
No. of measured, independent and
observed [I > 2σ(I)] reflections
9116, 2343, 1411
Rint0.042
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.108, 1.01
No. of reflections2343
No. of parameters119
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.31

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

Help with the X-ray diffraction experiments by Dr A. Villinger and Dipl.-Chem. P. Thiele (University of Rostock) is gratefully acknowledged.

References

First citationAbdellatif, K. R., Velázquez, C. A., Huang, Z., Chowdhury, M. A. & Knaus, E. E. (2010). Bioorg. Med. Chem. Lett. 20, 5245–5250.  CrossRef CAS PubMed Google Scholar
First citationAbdellatif, K. R., Velázquez, C. A., Huang, Z., Chowdhury, M. A. & Knaus, E. E. (2011). Bioorg. Med. Chem. Lett. 21, 1195–1198.  CrossRef CAS PubMed Google Scholar
First citationBruker (2007). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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First citationShiina, I., Sano, Y., Nakata, K., Suzuki, M., Yokoyama, T., Sasaki, A., Orikasa, T., Miyamoto, T., Ikekita, M., Nagahara, Y. & Hasome, Y. (2007). Bioorg. Med. Chem. 15, 7599–7617.  CrossRef PubMed CAS Google Scholar
First citationUddin, M. J., Rao, P. N. P. & Knaus, E. E. (2004a). Bioorg. Med. Chem. 12, 5929–5940.  CrossRef PubMed CAS Google Scholar
First citationUddin, M. J., Rao, P. N. P. & Knaus, E. E. (2004b). Bioorg. Med. Chem. Lett. 14, 1953–1956.  CrossRef PubMed CAS Google Scholar

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