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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1585.
Published online 2010 June 5. doi:  10.1107/S1600536810021008
PMCID: PMC3006767

(3,4-Dimeth­oxy­phen­yl)(4-fluoro­phen­yl)methanone

Abstract

In the title compound, C15H13FO3, the dihedral angle between the two aromatic rings is 52.78 (8)°. In the crystal, inter­molecular C—H(...)O hydrogen bonds link mol­ecules into chains running parallel to the c axis.

Related literature

For applications of benzophenone and its derivatives, see: Riechers et al. (1996 [triangle]); Khanum et al. (2009 [triangle]); Schlecht et al. (2008 [triangle]).

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Object name is e-66-o1585-scheme1.jpg

Experimental

Crystal data

  • C15H13FO3
  • M r = 260.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1585-efi1.jpg
  • a = 10.8926 (9) Å
  • b = 11.3632 (11) Å
  • c = 10.8369 (10) Å
  • β = 108.285 (1)°
  • V = 1273.6 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.48 × 0.38 × 0.15 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.952, T max = 0.985
  • 6183 measured reflections
  • 2227 independent reflections
  • 1391 reflections with I > 2σ(I)
  • R int = 0.083

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.173
  • S = 1.00
  • 2227 reflections
  • 174 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021008/rz2456sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021008/rz2456Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 20572103).

supplementary crystallographic information

Comment

Benzophenone derivatives are an important class of compounds having a broad spectrum of applications in the chemical and biochemical fields (Riechers et al., 1996; Khanum et al., 2009), and are widely used as UV-screens to protect industrial products from light induced damage (Schlecht et al., 2008). In order to develop new applications for benzophenone and its derivatives, structural modifications of benzophenone have been extensively investigated. As a contribution to this field, we report here the crystal structure of the title compound.

The molecular structure of title compound is shown in Fig. 1. The dihedral angle formed by the benzene rings 52.78 (8)°. In the crystal packing (Fig. 2), intermolecular C—H···O hydrogen bonds (Table 1) link molecules into chains running parallel to the c axis.

Experimental

To a solution of 1,2-dimethoxybenzene (138 g, 1.00 mol) in dichloromethane (2.00 l), AlCl3 (199 g, 1.50 mol) was added. Then 4-fluorobenzoyl chloride (158 g, 2.00 mol) was added. The mixture was stirred at room temperature for 2 h, followed by filtration and purification by crystallization from ethyl acetate, giving the title compound as a colourless crystalline solid.

Refinement

All H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93-0.96 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of the compound, with atom labels and 50% probability displacement ellipsoids. Hydrogen atoms are omitted.
Fig. 2.
Crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

C15H13FO3F(000) = 544
Mr = 260.25Dx = 1.357 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1872 reflections
a = 10.8926 (9) Åθ = 2.7–26.1°
b = 11.3632 (11) ŵ = 0.10 mm1
c = 10.8369 (10) ÅT = 298 K
β = 108.285 (1)°Needle, colourless
V = 1273.6 (2) Å30.48 × 0.38 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2227 independent reflections
Radiation source: fine-focus sealed tube1391 reflections with I > 2σ(I)
graphiteRint = 0.083
phi and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→12
Tmin = 0.952, Tmax = 0.985k = −13→13
6183 measured reflectionsl = −12→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0915P)2] where P = (Fo2 + 2Fc2)/3
2227 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.32 e Å3

Special details

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)

xyzUiso*/Ueq
F10.13858 (16)0.52452 (18)−0.33034 (17)0.0864 (7)
O10.46324 (18)0.62209 (18)0.24672 (19)0.0638 (6)
O20.88706 (15)0.85244 (17)0.40525 (17)0.0555 (6)
O30.86314 (15)1.01546 (15)0.23481 (17)0.0512 (5)
C10.4782 (2)0.6672 (2)0.1495 (3)0.0433 (6)
C20.5825 (2)0.7552 (2)0.1622 (2)0.0384 (6)
C30.6868 (2)0.7580 (2)0.2777 (2)0.0420 (6)
H30.69280.70150.34140.050*
C40.7801 (2)0.8432 (2)0.2976 (2)0.0405 (6)
C50.7682 (2)0.9316 (2)0.2037 (2)0.0392 (6)
C60.6666 (2)0.9291 (2)0.0898 (2)0.0416 (6)
H60.65970.98650.02690.050*
C70.5739 (2)0.8405 (2)0.0688 (2)0.0399 (6)
H70.50570.8387−0.00860.048*
C80.8996 (3)0.7711 (3)0.5078 (3)0.0682 (9)
H8A0.82720.77900.53970.102*
H8B0.97820.78670.57680.102*
H8C0.90200.69250.47610.102*
C90.8510 (3)1.1108 (3)0.1468 (3)0.0664 (9)
H9A0.85061.08110.06370.100*
H9B0.92251.16370.17980.100*
H9C0.77151.15190.13740.100*
C100.3889 (2)0.6332 (2)0.0193 (2)0.0396 (6)
C110.2630 (2)0.6010 (2)0.0084 (3)0.0475 (7)
H110.23550.60420.08130.057*
C120.1782 (3)0.5644 (2)−0.1084 (3)0.0545 (7)
H120.09380.5431−0.11540.065*
C130.2215 (3)0.5604 (3)−0.2141 (3)0.0554 (8)
C140.3456 (3)0.5881 (3)−0.2083 (3)0.0559 (8)
H140.37280.5816−0.28120.067*
C150.4290 (2)0.6260 (2)−0.0911 (3)0.0462 (7)
H150.51310.6470−0.08540.055*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0788 (12)0.1100 (15)0.0628 (12)−0.0321 (12)0.0113 (9)−0.0168 (10)
O10.0677 (13)0.0799 (14)0.0502 (12)−0.0215 (11)0.0274 (10)0.0033 (10)
O20.0450 (11)0.0706 (13)0.0473 (11)−0.0113 (9)0.0094 (9)0.0127 (9)
O30.0463 (11)0.0513 (11)0.0573 (12)−0.0076 (9)0.0183 (8)0.0060 (9)
C10.0400 (14)0.0476 (15)0.0491 (16)0.0021 (12)0.0239 (12)0.0029 (12)
C20.0338 (13)0.0456 (14)0.0422 (14)0.0041 (11)0.0210 (10)−0.0028 (11)
C30.0398 (14)0.0480 (15)0.0446 (15)0.0002 (12)0.0223 (11)0.0055 (12)
C40.0317 (13)0.0504 (15)0.0427 (15)0.0043 (12)0.0165 (11)0.0016 (12)
C50.0366 (13)0.0412 (14)0.0457 (15)0.0032 (12)0.0215 (11)−0.0022 (11)
C60.0440 (14)0.0427 (14)0.0433 (14)0.0050 (12)0.0210 (11)0.0036 (11)
C70.0353 (13)0.0463 (14)0.0402 (14)0.0060 (12)0.0148 (10)−0.0010 (11)
C80.0643 (19)0.080 (2)0.0492 (17)−0.0084 (17)0.0021 (14)0.0185 (16)
C90.076 (2)0.0543 (17)0.069 (2)−0.0170 (16)0.0224 (16)0.0105 (15)
C100.0358 (13)0.0402 (14)0.0490 (16)−0.0007 (11)0.0225 (11)0.0006 (11)
C110.0426 (14)0.0522 (16)0.0568 (17)−0.0010 (13)0.0286 (12)0.0019 (13)
C120.0389 (14)0.0595 (18)0.0688 (19)−0.0084 (14)0.0223 (13)−0.0028 (15)
C130.0566 (17)0.0554 (18)0.0515 (17)−0.0119 (15)0.0132 (13)−0.0072 (14)
C140.0630 (18)0.0610 (18)0.0541 (18)−0.0105 (15)0.0332 (14)−0.0102 (14)
C150.0396 (14)0.0513 (15)0.0560 (17)−0.0068 (13)0.0267 (12)−0.0057 (13)

Geometric parameters (Å, °)

F1—C131.362 (3)C8—H8A0.9600
O1—C11.227 (3)C8—H8B0.9600
O2—C41.370 (3)C8—H8C0.9600
O2—C81.419 (3)C9—H9A0.9600
O3—C51.368 (3)C9—H9B0.9600
O3—C91.422 (3)C9—H9C0.9600
C1—C21.488 (3)C10—C111.388 (3)
C1—C101.493 (3)C10—C151.399 (3)
C2—C71.383 (3)C11—C121.377 (4)
C2—C31.402 (3)C11—H110.9300
C3—C41.370 (3)C12—C131.370 (4)
C3—H30.9300C12—H120.9300
C4—C51.407 (4)C13—C141.370 (4)
C5—C61.376 (3)C14—C151.378 (4)
C6—C71.393 (3)C14—H140.9300
C6—H60.9300C15—H150.9300
C7—H70.9300
C4—O2—C8117.6 (2)H8A—C8—H8C109.5
C5—O3—C9117.5 (2)H8B—C8—H8C109.5
O1—C1—C2120.3 (2)O3—C9—H9A109.5
O1—C1—C10118.7 (2)O3—C9—H9B109.5
C2—C1—C10120.9 (2)H9A—C9—H9B109.5
C7—C2—C3119.2 (2)O3—C9—H9C109.5
C7—C2—C1121.9 (2)H9A—C9—H9C109.5
C3—C2—C1118.6 (2)H9B—C9—H9C109.5
C4—C3—C2120.6 (2)C11—C10—C15118.5 (2)
C4—C3—H3119.7C11—C10—C1118.8 (2)
C2—C3—H3119.7C15—C10—C1122.6 (2)
C3—C4—O2125.4 (2)C12—C11—C10121.2 (2)
C3—C4—C5119.7 (2)C12—C11—H11119.4
O2—C4—C5114.9 (2)C10—C11—H11119.4
O3—C5—C6124.7 (2)C13—C12—C11118.1 (2)
O3—C5—C4115.4 (2)C13—C12—H12121.0
C6—C5—C4119.9 (2)C11—C12—H12121.0
C5—C6—C7120.0 (2)F1—C13—C12118.7 (2)
C5—C6—H6120.0F1—C13—C14118.0 (3)
C7—C6—H6120.0C12—C13—C14123.2 (3)
C2—C7—C6120.5 (2)C13—C14—C15118.0 (3)
C2—C7—H7119.8C13—C14—H14121.0
C6—C7—H7119.8C15—C14—H14121.0
O2—C8—H8A109.5C14—C15—C10120.9 (2)
O2—C8—H8B109.5C14—C15—H15119.5
H8A—C8—H8B109.5C10—C15—H15119.5
O2—C8—H8C109.5
O1—C1—C2—C7−153.7 (3)C3—C2—C7—C6−0.9 (3)
C10—C1—C2—C725.5 (3)C1—C2—C7—C6173.2 (2)
O1—C1—C2—C320.4 (3)C5—C6—C7—C20.5 (3)
C10—C1—C2—C3−160.4 (2)O1—C1—C10—C1130.4 (3)
C7—C2—C3—C4−0.7 (4)C2—C1—C10—C11−148.8 (2)
C1—C2—C3—C4−175.1 (2)O1—C1—C10—C15−145.9 (3)
C2—C3—C4—O2−178.5 (2)C2—C1—C10—C1534.9 (3)
C2—C3—C4—C52.7 (4)C15—C10—C11—C12−1.0 (4)
C8—O2—C4—C3−3.3 (4)C1—C10—C11—C12−177.4 (2)
C8—O2—C4—C5175.4 (2)C10—C11—C12—C130.2 (4)
C9—O3—C5—C64.3 (3)C11—C12—C13—F1−179.9 (2)
C9—O3—C5—C4−176.1 (2)C11—C12—C13—C141.6 (5)
C3—C4—C5—O3177.30 (19)F1—C13—C14—C15179.1 (2)
O2—C4—C5—O3−1.6 (3)C12—C13—C14—C15−2.4 (5)
C3—C4—C5—C6−3.1 (4)C13—C14—C15—C101.5 (4)
O2—C4—C5—C6178.1 (2)C11—C10—C15—C140.2 (4)
O3—C5—C6—C7−179.0 (2)C1—C10—C15—C14176.5 (2)
C4—C5—C6—C71.4 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.932.583.343 (3)139

Symmetry codes: (i) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2456).

References

  • Khanum, S. A., Girish, V., Suparshwa, S. S., Khanum, N. F. (2009). Bioorg. Med. Chem. Lett.19, 1887–1891. [PubMed]
  • Riechers, H., Albrecht, H.-P. & Amberg, W. (1996). J. Med. Chem.39, 2123–2128.. [PubMed]
  • Schlecht, C., Klammer, H., Frauendorf, H., Wuttke, W. & Jarry, H. (2008). Toxicology, 245, 11–17. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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