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

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ISSN: 2056-9890

Methyl 2-(4-hy­dr­oxy­benzo­yl)benzoate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Chemistry, Sambhram Institute of Technology, Bengaluru, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 4 July 2011; accepted 4 July 2011; online 9 July 2011)

In the title compound, C15H12O4, the dihedral angle between the benzene rings is 64.0 (6)°. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming C(8) chains propagating in [10[\overline{1}]] and the packing is reinforced by weak C—H⋯O inter­actions.

Related literature

For background to benzophenone derivatives, see: Sieroń et al. (2004)[Sieroń, L., Shashikanth, S., Yathirajan, H. S., Venu, T. D., Nagaraj, B., Nagaraja, P. & Khanum, S. A. (2004). Acta Cryst. E60, o1889-o1891.]. For related structures, see: Cox et al. (2008[Cox, P. J., Kechagias, D. & Kelly, O. (2008). Acta Cryst. B64, 206-216.]); Jasinski et al. (2009[Jasinski, J. P., Butcher, R. J., Hakim Al-Arique, Q. N. M., Yathirajan, H. S. & Ramesha, A. R. (2009). Acta Cryst. E65, o1908-o1909.]). For reference 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
  • C15H12O4

  • Mr = 256.25

  • Monoclinic, P 21 /n

  • a = 8.9017 (12) Å

  • b = 13.9940 (17) Å

  • c = 10.0473 (12) Å

  • β = 94.687 (12)°

  • V = 1247.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 173 K

  • 0.38 × 0.32 × 0.24 mm

Data collection
  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.963, Tmax = 0.977

  • 11331 measured reflections

  • 3231 independent reflections

  • 2722 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.02

  • 3231 reflections

  • 177 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O4—H4O⋯O3i 0.85 (1) 1.88 (2) 2.7310 (14) 173 (2)
C12—H12A⋯O2i 0.95 2.50 3.4333 (15) 167
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound is a starting material for the synthesis of pitofenone, which is an antispasmodic. More generally, benzophenone derivatives have many applications in organic chemistry (Sieroń et al., 2004). The crystal structures of some substituted benzophenones (Cox et al., 2008) and 2-amino-5-nitrophenyl 2-chlorophenyl ketone (Jasinski et al., 2009) have been reported. In view of the importance of the title compound, this paper reports the crystal structure of (I), C15H12O4.

In the title compound, C15H12O4, the dihedral angle between the mean planes of the two benzene rings is 64.0 (6)° (Fig. 1). Bond distances are in normal ranges (Allen et al., 1987). Crystal packing is stabilized by O—H···O hydrogen bonds and weak C—H···O intermolecular interactions (Table 1, Fig. 2).

Related literature top

For background to benzophenone derivatives, see: Sieroń et al. (2004). For related structures, see: Cox et al. (2008); Jasinski et al. (2009). For reference bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem, Bengaluru, india. Colourless blocks were grown from methanol solution (430-433 K).

Refinement top

The O–H atom was located by Fourier analysis and refined isotropically with DFIX = 0.84Å. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom–H lengths of 0.95Å (CH) or 0.98Å (CH3). Isotropic displacement parameters for these atoms were set to 1.18-1.20 (CH) or 1.51 (CH3) times Ueq of the parent atom.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the c axis. Dashed lines represent O—H···O hydrogen bonds.
Methyl 2-(4-hydroxybenzoyl)benzoate top
Crystal data top
C15H12O4F(000) = 536
Mr = 256.25Dx = 1.364 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4807 reflections
a = 8.9017 (12) Åθ = 3.3–32.3°
b = 13.9940 (17) ŵ = 0.10 mm1
c = 10.0473 (12) ÅT = 173 K
β = 94.687 (12)°Block, colorless
V = 1247.4 (3) Å30.38 × 0.32 × 0.24 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer
3231 independent reflections
Radiation source: Enhance (Mo) X-ray Source2722 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 16.1500 pixels mm-1θmax = 28.7°, θmin = 3.3°
ω scansh = 1112
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)
k = 1818
Tmin = 0.963, Tmax = 0.977l = 1213
11331 measured reflections
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)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0567P)2 + 0.3281P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3231 reflectionsΔρmax = 0.25 e Å3
177 parametersΔρmin = 0.18 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.059 (4)
Crystal data top
C15H12O4V = 1247.4 (3) Å3
Mr = 256.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.9017 (12) ŵ = 0.10 mm1
b = 13.9940 (17) ÅT = 173 K
c = 10.0473 (12) Å0.38 × 0.32 × 0.24 mm
β = 94.687 (12)°
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer
3231 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)
2722 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.977Rint = 0.020
11331 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0421 restraint
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.25 e Å3
3231 reflectionsΔρmin = 0.18 e Å3
177 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O10.67772 (14)0.53971 (7)1.02990 (9)0.0554 (3)
O20.65842 (11)0.66691 (6)0.89536 (10)0.0444 (2)
O30.46662 (10)0.59366 (8)0.66899 (10)0.0467 (3)
O40.67624 (12)0.86689 (8)0.21951 (11)0.0538 (3)
H4O0.7691 (17)0.8749 (14)0.2078 (19)0.065*
C10.6277 (3)0.59825 (13)1.13629 (15)0.0679 (5)
H1A0.63250.56111.21920.102*
H1B0.52360.61891.11310.102*
H1C0.69300.65451.14870.102*
C20.68941 (13)0.58440 (9)0.91453 (12)0.0353 (3)
C30.75070 (13)0.52066 (8)0.81331 (12)0.0339 (3)
C40.85127 (16)0.44807 (10)0.85257 (14)0.0452 (3)
H4A0.87480.43570.94490.054*
C50.91727 (18)0.39370 (11)0.75845 (17)0.0531 (4)
H5A0.98500.34370.78620.064*
C60.88503 (17)0.41180 (10)0.62450 (16)0.0494 (3)
H6A0.93080.37450.55990.059*
C70.78597 (15)0.48435 (9)0.58380 (13)0.0404 (3)
H7A0.76540.49720.49130.048*
C80.71643 (12)0.53855 (8)0.67704 (11)0.0322 (2)
C90.59158 (13)0.60509 (8)0.62820 (11)0.0326 (2)
C100.61847 (12)0.67596 (8)0.52514 (11)0.0308 (2)
C110.76378 (12)0.70441 (8)0.49875 (12)0.0331 (3)
H11A0.84830.67840.55020.040*
C120.78631 (13)0.76950 (9)0.39946 (12)0.0353 (3)
H12A0.88550.78900.38350.042*
C130.66243 (14)0.80656 (9)0.32274 (12)0.0359 (3)
C140.51685 (13)0.78068 (9)0.34968 (13)0.0384 (3)
H14A0.43250.80730.29870.046*
C150.49546 (13)0.71679 (9)0.44985 (12)0.0352 (3)
H15A0.39590.70000.46840.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0885 (8)0.0476 (6)0.0317 (5)0.0005 (5)0.0142 (5)0.0028 (4)
O20.0508 (5)0.0381 (5)0.0459 (5)0.0019 (4)0.0124 (4)0.0004 (4)
O30.0334 (5)0.0645 (6)0.0436 (5)0.0006 (4)0.0112 (4)0.0083 (4)
O40.0446 (5)0.0645 (7)0.0533 (6)0.0042 (5)0.0097 (5)0.0255 (5)
C10.1059 (15)0.0657 (10)0.0344 (7)0.0035 (10)0.0198 (8)0.0063 (7)
C20.0359 (6)0.0384 (6)0.0315 (6)0.0050 (5)0.0029 (4)0.0014 (4)
C30.0351 (6)0.0321 (5)0.0349 (6)0.0029 (4)0.0046 (4)0.0023 (4)
C40.0487 (7)0.0425 (7)0.0443 (7)0.0041 (5)0.0037 (6)0.0103 (5)
C50.0536 (8)0.0420 (7)0.0647 (9)0.0140 (6)0.0101 (7)0.0088 (6)
C60.0512 (8)0.0415 (7)0.0572 (9)0.0084 (6)0.0144 (6)0.0060 (6)
C70.0430 (7)0.0410 (6)0.0379 (6)0.0008 (5)0.0081 (5)0.0042 (5)
C80.0318 (5)0.0317 (5)0.0337 (6)0.0026 (4)0.0054 (4)0.0004 (4)
C90.0308 (5)0.0383 (6)0.0289 (5)0.0003 (4)0.0041 (4)0.0033 (4)
C100.0287 (5)0.0350 (6)0.0289 (5)0.0018 (4)0.0036 (4)0.0028 (4)
C110.0274 (5)0.0398 (6)0.0317 (5)0.0021 (4)0.0005 (4)0.0015 (4)
C120.0286 (5)0.0408 (6)0.0368 (6)0.0018 (4)0.0056 (4)0.0004 (5)
C130.0376 (6)0.0374 (6)0.0335 (6)0.0036 (5)0.0066 (5)0.0019 (5)
C140.0305 (5)0.0470 (7)0.0375 (6)0.0081 (5)0.0015 (4)0.0045 (5)
C150.0257 (5)0.0438 (6)0.0365 (6)0.0019 (4)0.0043 (4)0.0001 (5)
Geometric parameters (Å, º) top
O1—C21.3286 (15)C6—C71.3844 (19)
O1—C11.4458 (18)C6—H6A0.9500
O2—C21.1991 (15)C7—C81.3895 (17)
O3—C91.2270 (14)C7—H7A0.9500
O4—C131.3508 (15)C8—C91.5013 (16)
O4—H4O0.852 (14)C9—C101.4675 (16)
C1—H1A0.9800C10—C111.3993 (15)
C1—H1B0.9800C10—C151.4009 (16)
C1—H1C0.9800C11—C121.3777 (17)
C2—C31.4894 (17)C11—H11A0.9500
C3—C41.3896 (18)C12—C131.3930 (17)
C3—C81.4007 (16)C12—H12A0.9500
C4—C51.382 (2)C13—C141.3932 (17)
C4—H4A0.9500C14—C151.3711 (17)
C5—C61.377 (2)C14—H14A0.9500
C5—H5A0.9500C15—H15A0.9500
C2—O1—C1115.42 (12)C8—C7—H7A119.7
C13—O4—H4O109.8 (13)C7—C8—C3119.21 (11)
O1—C1—H1A109.5C7—C8—C9118.48 (10)
O1—C1—H1B109.5C3—C8—C9121.78 (10)
H1A—C1—H1B109.5O3—C9—C10121.90 (11)
O1—C1—H1C109.5O3—C9—C8118.49 (11)
H1A—C1—H1C109.5C10—C9—C8119.39 (10)
H1B—C1—H1C109.5C11—C10—C15118.39 (10)
O2—C2—O1124.05 (12)C11—C10—C9122.18 (10)
O2—C2—C3124.01 (11)C15—C10—C9119.43 (10)
O1—C2—C3111.90 (10)C12—C11—C10121.12 (10)
C4—C3—C8119.47 (11)C12—C11—H11A119.4
C4—C3—C2120.49 (11)C10—C11—H11A119.4
C8—C3—C2119.85 (10)C11—C12—C13119.43 (11)
C5—C4—C3120.55 (13)C11—C12—H12A120.3
C5—C4—H4A119.7C13—C12—H12A120.3
C3—C4—H4A119.7O4—C13—C12122.68 (11)
C6—C5—C4120.09 (13)O4—C13—C14117.13 (11)
C6—C5—H5A120.0C12—C13—C14120.18 (11)
C4—C5—H5A120.0C15—C14—C13119.95 (11)
C5—C6—C7120.04 (13)C15—C14—H14A120.0
C5—C6—H6A120.0C13—C14—H14A120.0
C7—C6—H6A120.0C14—C15—C10120.87 (10)
C6—C7—C8120.61 (12)C14—C15—H15A119.6
C6—C7—H7A119.7C10—C15—H15A119.6
C1—O1—C2—O21.6 (2)C3—C8—C9—O351.01 (16)
C1—O1—C2—C3176.40 (13)C7—C8—C9—C1054.18 (15)
O2—C2—C3—C4147.15 (13)C3—C8—C9—C10134.26 (12)
O1—C2—C3—C430.85 (16)O3—C9—C10—C11165.69 (12)
O2—C2—C3—C827.74 (18)C8—C9—C10—C1119.76 (16)
O1—C2—C3—C8154.27 (11)O3—C9—C10—C1514.46 (17)
C8—C3—C4—C50.0 (2)C8—C9—C10—C15160.09 (11)
C2—C3—C4—C5174.93 (12)C15—C10—C11—C121.31 (17)
C3—C4—C5—C60.7 (2)C9—C10—C11—C12178.54 (11)
C4—C5—C6—C70.2 (2)C10—C11—C12—C130.95 (18)
C5—C6—C7—C81.0 (2)C11—C12—C13—O4176.60 (12)
C6—C7—C8—C31.68 (19)C11—C12—C13—C142.41 (18)
C6—C7—C8—C9170.10 (12)O4—C13—C14—C15177.49 (12)
C4—C3—C8—C71.16 (17)C12—C13—C14—C151.58 (19)
C2—C3—C8—C7173.77 (11)C13—C14—C15—C100.74 (19)
C4—C3—C8—C9170.33 (11)C11—C10—C15—C142.16 (17)
C2—C3—C8—C914.73 (16)C9—C10—C15—C14177.69 (11)
C7—C8—C9—O3120.55 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O3i0.85 (1)1.88 (2)2.7310 (14)173 (2)
C12—H12A···O2i0.952.503.4333 (15)167
Symmetry code: (i) x+1/2, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC15H12O4
Mr256.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)8.9017 (12), 13.9940 (17), 10.0473 (12)
β (°) 94.687 (12)
V3)1247.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.38 × 0.32 × 0.24
Data collection
DiffractometerOxford Diffraction Xcalibur Eos Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2010)
Tmin, Tmax0.963, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
11331, 3231, 2722
Rint0.020
(sin θ/λ)max1)0.676
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.02
No. of reflections3231
No. of parameters177
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O3i0.852 (14)1.883 (15)2.7310 (14)172.8 (19)
C12—H12A···O2i0.952.503.4333 (15)167
Symmetry code: (i) x+1/2, y+3/2, z1/2.
 

Acknowledgements

MSS thanks the University of Mysore for the research facilities and HSY thanks R. L. Fine Chem, Bengaluru, India, for a gift sample of the title compound. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

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 citationCox, P. J., Kechagias, D. & Kelly, O. (2008). Acta Cryst. B64, 206–216.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationJasinski, J. P., Butcher, R. J., Hakim Al-Arique, Q. N. M., Yathirajan, H. S. & Ramesha, A. R. (2009). Acta Cryst. E65, o1908–o1909.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSieroń, L., Shashikanth, S., Yathirajan, H. S., Venu, T. D., Nagaraj, B., Nagaraja, P. & Khanum, S. A. (2004). Acta Cryst. E60, o1889–o1891.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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