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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 6| June 2012| Page o1676
doi:10.1107/S1600536812019812

Methyl 2-[4-(4-chloro­benzo­yl)phen­­oxy]-2-methyl­propano­ate

Baohua Zou,a Zheng Fang,a Hui Zhong,a Kai Guob* and Ping Weib

aSchool of Pharmaceutical Sciences, Nanjing University of Technology, Puzhunan Road No. 30 Nanjing, Nanjing 210009, People's Republic of China, and bCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Puzhunan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
*Correspondence e-mail: kaiguo@njut.edu.cn

(Received 12 April 2012; accepted 3 May 2012; online 12 May 2012)

In the title compound, C18H17ClO4, the dihedral angle between the mean planes of the benzene rings is 53.4 (1)°. Weak inter­molecular C—H⋯O inter­actions are observed.

Related literature

For background, see: Guichard et al. (2000[Guichard, J. P., Blouquin, P. & Qing, Y. (2000). Curr. Med. Res. Opin. 16, 134-138.]). For the synthesis of the title compound, see: Bandgar et al. (2011[Bandgar, B. P., Sarangdhar, R. J., Khan, F., Mookkan, J., Shetty, P. & Singh, G. (2011). J. Med. Chem. 54, 5915-5926.]). For bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C18H17ClO4

  • Mr = 332.77

  • Orthorhombic, P b c a

  • a = 19.657 (4) Å

  • b = 7.5860 (15) Å

  • c = 22.436 (5) Å

  • V = 3345.6 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.930, Tmax = 0.976

  • 6018 measured reflections

  • 3065 independent reflections

  • 1432 reflections with I > 2σ(I)

  • Rint = 0.092
Refinement

  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.194

  • S = 1.00

  • 3065 reflections

  • 208 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1A⋯O3i 0.93 2.37 3.254 (6) 159
Symmetry code: (i) x, y-1, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019812/jj2129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019812/jj2129Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019812/jj2129Isup3.cml

checkCIF report


Comment top

The title compound, C18H17ClO4, (I), is a derivative of Fenofibrate, a antihypertensive drug (Guichard et al. 2000). We report herein its crystal structure.

In the title compound, (I), the dihedral angle between the mean planes of the benzene and phenyl rings is 53.4 (1)°. Crystal packing is influenced by weak C—H···O intermolecular interactions. Bond lengths are in normal ranges (Allen et al. 1987).

Related literature top

For background, see: Guichard et al., (2000). For the synthesis of the title compound, see: Bandgar et al. (2011). For bond lengths, see: Allen et al. (1987).

Experimental top

2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid (6.28 mmol, 2.00 g) was dissolved in 35% hydrochloric acid methanol solution (15 mL), the solution was heated to 338.15 K under N2 atmosphere for 3 h. The reaction mexture was cooled to room temperature and the solvent was distilled to get the crude compound. The crude compond was dissolved in dichloromethane (15 mL), washed with water (10 mL) three times, dried, and concentrated to get the title compound (1.95 g). pure: white solid (Bandgar et al. 2011). Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement top

H atoms were positioned geometrically with C—H = 0.93, 0.98 and 0.97 Å for aromatic, methine and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 (or 1.5 for methyl groups) times Ueq(C).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, (I), showing the atom labeling scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the a axis. Dashed lines indicate weak C—H···O intermolecular interactions. Remaining H atoms have been omitted for clarity.
Methyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate top
Crystal data top
C18H17ClO4F(000) = 1392
Mr = 332.77Dx = 1.321 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 19.657 (4) Åθ = 9–12°
b = 7.5860 (15) ŵ = 0.25 mm−1
c = 22.436 (5) ÅT = 293 K
V = 3345.6 (12) Å3Block, colorless
Z = 80.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		3065 independent reflections
Radiation source: fine-focus sealed tube1432 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.092
Detector resolution: 16.0355 pixels mm-1θmax = 25.4°, θmin = 1.8°
ω/2θ scansh = 0→23
Absorption correction: ψ scan
(North et al., 1968)		k = 0→9
Tmin = 0.930, Tmax = 0.976l = −27→27
6018 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.070P)2 + 1.P]
where P = (Fo2 + 2Fc2)/3
3065 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C18H17ClO4V = 3345.6 (12) Å3
Mr = 332.77Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 19.657 (4) ŵ = 0.25 mm−1
b = 7.5860 (15) ÅT = 293 K
c = 22.436 (5) Å0.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		3065 independent reflections
Absorption correction: ψ scan
(North et al., 1968)		1432 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.976Rint = 0.092
6018 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.194H-atom parameters constrained
S = 1.00Δρmax = 0.20 e Å−3
3065 reflectionsΔρmin = −0.21 e Å−3
208 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl0.19155 (8)0.28985 (19)0.10094 (7)0.0861 (5)
O10.03598 (16)1.0570 (4)0.15179 (15)0.0650 (10)
O20.18493 (16)1.3480 (4)0.38182 (14)0.0641 (9)
O30.1333 (2)1.6697 (5)0.34807 (16)0.0758 (11)
O40.07842 (17)1.7018 (4)0.43384 (15)0.0688 (10)
C10.1314 (2)0.6897 (6)0.2032 (2)0.0513 (12)
H1A0.13110.71550.24370.062*
C20.1552 (2)0.5266 (6)0.1842 (2)0.0569 (12)
H2A0.16940.44290.21190.068*
C30.1576 (2)0.4899 (7)0.1245 (2)0.0576 (13)
C40.1335 (3)0.6088 (7)0.0831 (2)0.0627 (13)
H4A0.13410.58150.04270.075*
C50.1087 (2)0.7686 (7)0.1024 (2)0.0579 (13)
H5A0.09170.84810.07450.069*
C60.1083 (2)0.8146 (6)0.16303 (18)0.0451 (11)
C70.0807 (2)0.9881 (6)0.1814 (2)0.0496 (11)
C80.1063 (2)1.0766 (6)0.23639 (19)0.0461 (11)
C90.0652 (2)1.1914 (6)0.2664 (2)0.0583 (13)
H9A0.02071.20710.25340.070*
C100.0875 (2)1.2857 (6)0.3158 (2)0.0576 (12)
H10A0.05841.36190.33590.069*
C110.1539 (2)1.2636 (6)0.33445 (19)0.0502 (11)
C120.1967 (2)1.1497 (6)0.3040 (2)0.0523 (12)
H12A0.24171.13680.31620.063*
C130.1730 (2)1.0555 (6)0.2559 (2)0.0519 (11)
H13A0.20170.97730.23630.062*
C140.1484 (2)1.4503 (6)0.42572 (19)0.0488 (11)
C150.0947 (3)1.3430 (6)0.4578 (2)0.0746 (16)
H15A0.11541.24080.47530.112*
H15B0.06041.30660.42990.112*
H15C0.07421.41340.48850.112*
C160.2051 (2)1.5112 (7)0.4665 (2)0.0657 (14)
H16A0.22491.41100.48610.099*
H16B0.18701.59040.49590.099*
H16D0.23921.57070.44350.099*
C170.1192 (2)1.6172 (6)0.3962 (2)0.0544 (12)
C180.0490 (3)1.8640 (6)0.4124 (3)0.096 (2)
H18D0.02061.91410.44280.143*
H18A0.02231.84050.37750.143*
H18B0.08471.94540.40260.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.1045 (12)0.0681 (9)0.0857 (11)0.0090 (8)0.0163 (9)−0.0196 (8)
O10.055 (2)0.055 (2)0.085 (2)−0.0014 (17)−0.0228 (18)0.0061 (18)
O20.058 (2)0.069 (2)0.065 (2)0.0090 (17)−0.0062 (16)−0.0251 (18)
O30.095 (3)0.070 (2)0.063 (2)−0.005 (2)0.008 (2)0.0145 (19)
O40.081 (2)0.054 (2)0.072 (2)0.0153 (18)0.008 (2)−0.0068 (18)
C10.058 (3)0.057 (3)0.039 (2)−0.009 (2)−0.005 (2)−0.001 (2)
C20.059 (3)0.051 (3)0.060 (3)0.004 (2)0.000 (2)0.003 (2)
C30.055 (3)0.060 (3)0.058 (3)−0.006 (2)0.008 (2)−0.014 (3)
C40.080 (4)0.065 (3)0.043 (3)−0.009 (3)−0.005 (3)−0.009 (3)
C50.067 (3)0.064 (3)0.043 (3)−0.010 (3)−0.007 (2)0.010 (2)
C60.043 (2)0.051 (3)0.041 (2)−0.008 (2)−0.001 (2)0.003 (2)
C70.045 (2)0.042 (3)0.061 (3)0.002 (2)−0.001 (2)0.004 (2)
C80.041 (2)0.049 (3)0.048 (3)−0.003 (2)−0.006 (2)0.003 (2)
C90.041 (2)0.059 (3)0.075 (3)0.004 (2)−0.001 (2)−0.005 (3)
C100.043 (2)0.053 (3)0.076 (3)0.007 (2)0.006 (3)−0.012 (3)
C110.052 (3)0.048 (3)0.051 (3)−0.001 (2)−0.005 (2)−0.006 (2)
C120.046 (2)0.049 (3)0.062 (3)0.004 (2)−0.006 (2)−0.009 (2)
C130.044 (3)0.044 (3)0.067 (3)0.001 (2)−0.002 (2)−0.011 (2)
C140.055 (3)0.045 (3)0.046 (3)−0.006 (2)−0.003 (2)−0.006 (2)
C150.095 (4)0.057 (3)0.072 (4)−0.009 (3)0.013 (3)0.007 (3)
C160.078 (3)0.060 (3)0.059 (3)0.001 (3)−0.013 (3)−0.004 (3)
C170.059 (3)0.055 (3)0.049 (3)−0.005 (2)−0.002 (2)−0.008 (3)
C180.105 (5)0.048 (3)0.134 (6)0.028 (3)−0.013 (4)−0.021 (4)
Geometric parameters (Å, º) top
Cl—C31.740 (5)C9—C101.390 (6)
O1—C71.219 (5)C9—H9A0.9300
O2—C111.382 (5)C10—C111.381 (6)
O2—C141.445 (5)C10—H10A0.9300
O3—C171.183 (5)C11—C121.386 (6)
O4—C171.330 (5)C12—C131.377 (6)
O4—C181.442 (6)C12—H12A0.9300
C1—C61.385 (6)C13—H13A0.9300
C1—C21.390 (6)C14—C151.514 (6)
C1—H1A0.9300C14—C161.515 (6)
C2—C31.370 (6)C14—C171.539 (6)
C2—H2A0.9300C15—H15A0.9600
C3—C41.378 (7)C15—H15B0.9600
C4—C51.376 (6)C15—H15C0.9600
C4—H4A0.9300C16—H16A0.9600
C5—C61.405 (6)C16—H16B0.9600
C5—H5A0.9300C16—H16D0.9600
C6—C71.482 (6)C18—H18D0.9600
C7—C81.493 (6)C18—H18A0.9600
C8—C91.367 (6)C18—H18B0.9600
C8—C131.391 (5)
C11—O2—C14123.6 (3)O2—C11—C12113.5 (4)
C17—O4—C18116.2 (4)C13—C12—C11120.3 (4)
C6—C1—C2121.3 (4)C13—C12—H12A119.9
C6—C1—H1A119.3C11—C12—H12A119.9
C2—C1—H1A119.3C12—C13—C8120.4 (4)
C3—C2—C1119.5 (5)C12—C13—H13A119.8
C3—C2—H2A120.3C8—C13—H13A119.8
C1—C2—H2A120.3O2—C14—C15112.4 (4)
C2—C3—C4121.0 (5)O2—C14—C16102.1 (3)
C2—C3—Cl119.2 (4)C15—C14—C16112.9 (4)
C4—C3—Cl119.9 (4)O2—C14—C17109.5 (4)
C5—C4—C3119.2 (4)C15—C14—C17112.8 (4)
C5—C4—H4A120.4C16—C14—C17106.4 (3)
C3—C4—H4A120.4C14—C15—H15A109.5
C4—C5—C6121.6 (4)C14—C15—H15B109.5
C4—C5—H5A119.2H15A—C15—H15B109.5
C6—C5—H5A119.2C14—C15—H15C109.5
C1—C6—C5117.4 (4)H15A—C15—H15C109.5
C1—C6—C7123.2 (4)H15B—C15—H15C109.5
C5—C6—C7119.4 (4)C14—C16—H16A109.5
O1—C7—C6119.6 (4)C14—C16—H16B109.5
O1—C7—C8120.0 (4)H16A—C16—H16B109.5
C6—C7—C8120.4 (4)C14—C16—H16D109.5
C9—C8—C13118.4 (4)H16A—C16—H16D109.5
C9—C8—C7119.6 (4)H16B—C16—H16D109.5
C13—C8—C7121.8 (4)O3—C17—O4123.9 (5)
C8—C9—C10122.3 (4)O3—C17—C14125.6 (5)
C8—C9—H9A118.9O4—C17—C14110.4 (4)
C10—C9—H9A118.9O4—C18—H18D109.5
C11—C10—C9118.6 (4)O4—C18—H18A109.5
C11—C10—H10A120.7H18D—C18—H18A109.5
C9—C10—H10A120.7O4—C18—H18B109.5
C10—C11—O2126.4 (4)H18D—C18—H18B109.5
C10—C11—C12120.0 (4)H18A—C18—H18B109.5
C6—C1—C2—C31.8 (7)C9—C10—C11—O2179.0 (4)
C1—C2—C3—C4−3.3 (7)C9—C10—C11—C120.1 (7)
C1—C2—C3—Cl176.7 (4)C14—O2—C11—C1011.3 (7)
C2—C3—C4—C51.9 (7)C14—O2—C11—C12−169.7 (4)
Cl—C3—C4—C5−178.1 (4)C10—C11—C12—C13−1.2 (7)
C3—C4—C5—C61.1 (7)O2—C11—C12—C13179.7 (4)
C2—C1—C6—C51.1 (6)C11—C12—C13—C81.5 (7)
C2—C1—C6—C7178.2 (4)C9—C8—C13—C12−0.5 (7)
C4—C5—C6—C1−2.5 (6)C7—C8—C13—C12174.8 (4)
C4—C5—C6—C7−179.8 (4)C11—O2—C14—C1558.5 (5)
C1—C6—C7—O1−147.6 (4)C11—O2—C14—C16179.8 (4)
C5—C6—C7—O129.5 (6)C11—O2—C14—C17−67.7 (5)
C1—C6—C7—C831.1 (6)C18—O4—C17—O31.8 (7)
C5—C6—C7—C8−151.8 (4)C18—O4—C17—C14178.3 (4)
O1—C7—C8—C925.5 (6)O2—C14—C17—O3−11.3 (6)
C6—C7—C8—C9−153.2 (4)C15—C14—C17—O3−137.3 (5)
O1—C7—C8—C13−149.8 (4)C16—C14—C17—O398.3 (5)
C6—C7—C8—C1331.5 (6)O2—C14—C17—O4172.2 (3)
C13—C8—C9—C10−0.6 (7)C15—C14—C17—O446.3 (5)
C7—C8—C9—C10−176.1 (4)C16—C14—C17—O4−78.1 (5)
C8—C9—C10—C110.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O3i0.932.373.254 (6)159
Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC18H17ClO4
Mr332.77
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)19.657 (4), 7.5860 (15), 22.436 (5)
V (Å3)3345.6 (12)
Z8
Radiation typeMo Kα
µ (mm−1)0.25
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.930, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections		6018, 3065, 1432
Rint0.092
(sin θ/λ)max (Å−1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.194, 1.00
No. of reflections3065
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.20, −0.21

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O3i0.932.373.254 (6)159
Symmetry code: (i) x, y−1, z.
 

Acknowledgements

This research work was supported financially by the School of Pharmaceutical Science, Nanjing University of Technology and the `973' project (No. 2012CB725204) of the Key Basic Research Program of China.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationBandgar, B. P., Sarangdhar, R. J., Khan, F., Mookkan, J., Shetty, P. & Singh, G. (2011). J. Med. Chem. 54, 5915–5926.  Web of Science CrossRef CAS PubMed Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 6| June 2012| Page o1676
doi:10.1107/S1600536812019812
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