Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039542/gg2032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039542/gg2032Isup2.hkl |
CCDC reference: 660289
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.064
- wR factor = 0.242
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.50 Sigma PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.47 PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C1 -C6 1.34 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Phenylacetyl chloride (7.73 g, 0.05 mol) was added dropwise to p-cresol (5.41 g, 0.05 mol) and the mixture was reacted at room temperature for 1 h, then heated to 373 K for 2 h. After cooled to the ambient temperature, the CHCl3 diluted mixture was washed with sodium carbonate solution and water for several times. The organic layer was dried with anhydrous sodium sulfate, filtered, and the solvent was removed. Further purification was carried out by vacuum distillation, 4-methylphenyl phenylacetate was obtained (yield 81.2%). Then the mixture of 4-methylphenyl phenylacetate (9.19 g, 0.041 mol) and anhydrous aluminium chloride (17.20 g, 0.129 mol) gradually heated to 373 K in 0.5 h, then heated to 423 K and kept for 30 min. The reaction mixture was cooled to room temperature, hydrolyzed, and extracted with 60 ml CHCl3. The organic layer washed with water, dried with anhydrous sodium sulfate. Filtered, CHCl3 was removed under reduced pressure. The residue was distilled under vacuum to obtain the title compound (I) (yield 76.1%)·The compound was recrystallized from ethyl acetate to obtain colourless single crystals suitable for X-ray diffraction.
All H atoms,were positioned geometrically and treated as riding on their parent atoms,with C—H(methyl) = 0.96 Å, C—H(methylene) = 0.97 Å, C—H(aromatic) = 0.93 Å, O—H = 0.82 Å, and with Uiso(H)=1.5Ueq(Cmethyl,O) and 1.2Ueq(Caromatic,Cmethylene).
Benzophenones and related compounds have a wide variety of applications, in particular as biologically active compounds, which exhibit anti-inflammatory (Khanum et al., 2004), antifungal, antibacterial and anticancer activities·As an extension of work on the structural characterization of Benzophenone derivatives,the title compound, (I), was synthesized and its crystal structure is reported here.
The molecule of (I) is non-planar (Fig. 1). The dihedral angle between the two aromatic rings is 87.98 (13)°. The crystal structure is stabilized by intramolecular O—H···O hydrogen bonds and intermolecular O—H···C contacts together with C—H···π(arene) contacts and π···π stacking interactions, (Table 1, Fig. 2).
For related literature, see: Khanum et al. (2004).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C15H14O2 | F(000) = 480 |
Mr = 226.26 | Dx = 1.236 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3447 reflections |
a = 8.2951 (10) Å | θ = 2.3–25.1° |
b = 18.010 (2) Å | µ = 0.08 mm−1 |
c = 8.9186 (10) Å | T = 273 K |
β = 114.103 (4)° | Plate, colourless |
V = 1216.2 (2) Å3 | 0.35 × 0.24 × 0.18 mm |
Z = 4 |
Bruker APEX II CCD diffractometer | 2115 independent reflections |
Radiation source: fine-focus sealed tube | 1303 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −9→9 |
Tmin = 0.975, Tmax = 0.986 | k = −21→21 |
12849 measured reflections | l = −10→10 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.242 | w = 1/[σ2(Fo2) + (0.12P)2 + 0.7798P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
2115 reflections | Δρmax = 0.21 e Å−3 |
157 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.010 (4) |
C15H14O2 | V = 1216.2 (2) Å3 |
Mr = 226.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.2951 (10) Å | µ = 0.08 mm−1 |
b = 18.010 (2) Å | T = 273 K |
c = 8.9186 (10) Å | 0.35 × 0.24 × 0.18 mm |
β = 114.103 (4)° |
Bruker APEX II CCD diffractometer | 2115 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 1303 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.986 | Rint = 0.053 |
12849 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 1 restraint |
wR(F2) = 0.242 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.21 e Å−3 |
2115 reflections | Δρmin = −0.20 e Å−3 |
157 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.7193 (3) | 0.17283 (14) | 1.0078 (4) | 0.0955 (10) | |
H1 | 0.6678 | 0.2127 | 0.9949 | 0.143* | |
O2 | 0.6970 (3) | 0.31456 (13) | 0.9929 (4) | 0.0975 (11) | |
C1 | 0.8678 (4) | 0.18261 (17) | 1.0027 (5) | 0.0675 (10) | |
C2 | 0.9580 (5) | 0.12019 (19) | 1.0045 (5) | 0.0812 (11) | |
H2 | 0.9105 | 0.0737 | 1.0069 | 0.097* | |
C3 | 1.1103 (5) | 0.1267 (2) | 1.0029 (5) | 0.0811 (11) | |
H3 | 1.1754 | 0.0844 | 1.0044 | 0.097* | |
C4 | 1.1785 (4) | 0.1956 (2) | 0.9990 (5) | 0.0738 (11) | |
C5 | 1.0873 (4) | 0.25743 (18) | 0.9949 (5) | 0.0677 (10) | |
H5 | 1.1355 | 0.3036 | 0.9909 | 0.081* | |
C6 | 0.9320 (4) | 0.25309 (16) | 0.9965 (4) | 0.0578 (8) | |
C7 | 1.3490 (5) | 0.2031 (3) | 1.0001 (7) | 0.1133 (18) | |
H7A | 1.4366 | 0.1904 | 1.1068 | 0.170* | |
H7B | 1.3663 | 0.2535 | 0.9749 | 0.170* | |
H7C | 1.3596 | 0.1706 | 0.9194 | 0.170* | |
C8 | 0.8332 (4) | 0.31987 (17) | 0.9903 (5) | 0.0662 (10) | |
C9 | 0.9037 (4) | 0.39513 (18) | 0.9815 (5) | 0.0758 (11) | |
H9A | 1.0025 | 0.4045 | 1.0857 | 0.091* | |
H9B | 0.9504 | 0.3937 | 0.8980 | 0.091* | |
C10 | 0.7835 (4) | 0.45875 (17) | 0.9461 (5) | 0.0658 (10) | |
C11 | 0.6748 (5) | 0.4736 (2) | 0.7773 (6) | 0.0851 (12) | |
H11 | 0.6796 | 0.4434 | 0.6947 | 0.102* | |
C12 | 0.5657 (6) | 0.5323 (2) | 0.7409 (6) | 0.0960 (13) | |
H12 | 0.4928 | 0.5438 | 0.6326 | 0.115* | |
C13 | 0.5649 (5) | 0.5762 (2) | 0.8734 (6) | 0.0826 (12) | |
H13 | 0.4887 | 0.6167 | 0.8477 | 0.099* | |
C14 | 0.6721 (5) | 0.5627 (2) | 1.0419 (6) | 0.0808 (12) | |
H14 | 0.6672 | 0.5932 | 1.1241 | 0.097* | |
C15 | 0.7813 (4) | 0.50376 (19) | 1.0775 (5) | 0.0755 (11) | |
H15 | 0.8542 | 0.4924 | 1.1859 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0523 (14) | 0.0696 (16) | 0.172 (3) | −0.0098 (11) | 0.0535 (18) | 0.0088 (17) |
O2 | 0.0493 (14) | 0.0712 (16) | 0.189 (3) | 0.0004 (11) | 0.0659 (18) | 0.0089 (16) |
C1 | 0.0467 (17) | 0.0606 (19) | 0.094 (3) | −0.0052 (14) | 0.0273 (17) | 0.0027 (17) |
C2 | 0.063 (2) | 0.057 (2) | 0.126 (3) | −0.0018 (16) | 0.040 (2) | 0.0014 (19) |
C3 | 0.061 (2) | 0.064 (2) | 0.120 (3) | 0.0118 (16) | 0.038 (2) | 0.000 (2) |
C4 | 0.0425 (17) | 0.075 (2) | 0.108 (3) | 0.0081 (15) | 0.0350 (19) | 0.0017 (19) |
C5 | 0.0421 (17) | 0.0597 (19) | 0.103 (3) | −0.0007 (13) | 0.0312 (18) | 0.0020 (17) |
C6 | 0.0377 (15) | 0.0555 (18) | 0.081 (2) | −0.0021 (12) | 0.0249 (15) | 0.0018 (15) |
C7 | 0.052 (2) | 0.103 (3) | 0.197 (5) | 0.012 (2) | 0.063 (3) | 0.002 (3) |
C8 | 0.0439 (17) | 0.0604 (19) | 0.099 (3) | −0.0028 (13) | 0.0338 (18) | 0.0030 (17) |
C9 | 0.0464 (17) | 0.060 (2) | 0.125 (3) | 0.0004 (14) | 0.0383 (19) | 0.0051 (19) |
C10 | 0.0431 (16) | 0.0513 (17) | 0.104 (3) | −0.0018 (13) | 0.0312 (18) | 0.0016 (17) |
C11 | 0.080 (3) | 0.074 (2) | 0.102 (3) | 0.0155 (19) | 0.038 (2) | −0.007 (2) |
C12 | 0.083 (3) | 0.083 (3) | 0.106 (3) | 0.024 (2) | 0.022 (2) | 0.003 (2) |
C13 | 0.060 (2) | 0.060 (2) | 0.132 (4) | 0.0069 (15) | 0.044 (2) | 0.005 (2) |
C14 | 0.078 (3) | 0.066 (2) | 0.112 (3) | −0.0015 (18) | 0.052 (3) | −0.010 (2) |
C15 | 0.059 (2) | 0.069 (2) | 0.095 (3) | 0.0006 (16) | 0.0286 (19) | 0.003 (2) |
O1—C1 | 1.263 (4) | C7—H7C | 0.9600 |
O1—H1 | 0.8200 | C8—C9 | 1.491 (4) |
O2—C8 | 1.144 (4) | C9—C10 | 1.466 (4) |
C1—C2 | 1.347 (5) | C9—H9A | 0.9700 |
C1—C6 | 1.386 (4) | C9—H9B | 0.9700 |
C2—C3 | 1.274 (5) | C10—C11 | 1.429 (5) |
C2—H2 | 0.9300 | C10—C15 | 1.431 (5) |
C3—C4 | 1.371 (5) | C11—C12 | 1.342 (5) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.338 (4) | C12—C13 | 1.425 (6) |
C4—C7 | 1.417 (5) | C12—H12 | 0.9300 |
C5—C6 | 1.297 (4) | C13—C14 | 1.420 (6) |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
C6—C8 | 1.443 (4) | C14—C15 | 1.346 (5) |
C7—H7A | 0.9600 | C14—H14 | 0.9300 |
C7—H7B | 0.9600 | C15—H15 | 0.9300 |
C1—O1—H1 | 109.5 | O2—C8—C9 | 119.3 (3) |
O1—C1—C2 | 115.4 (3) | C6—C8—C9 | 122.1 (3) |
O1—C1—C6 | 121.7 (3) | C10—C9—C8 | 118.4 (3) |
C2—C1—C6 | 123.0 (3) | C10—C9—H9A | 107.7 |
C3—C2—C1 | 118.2 (3) | C8—C9—H9A | 107.7 |
C3—C2—H2 | 120.9 | C10—C9—H9B | 107.7 |
C1—C2—H2 | 120.9 | C8—C9—H9B | 107.7 |
C2—C3—C4 | 120.3 (3) | H9A—C9—H9B | 107.1 |
C2—C3—H3 | 119.9 | C11—C10—C15 | 122.9 (3) |
C4—C3—H3 | 119.9 | C11—C10—C9 | 117.0 (3) |
C5—C4—C3 | 121.3 (3) | C15—C10—C9 | 120.1 (3) |
C5—C4—C7 | 118.2 (3) | C12—C11—C10 | 118.4 (4) |
C3—C4—C7 | 120.5 (3) | C12—C11—H11 | 120.8 |
C6—C5—C4 | 120.2 (3) | C10—C11—H11 | 120.8 |
C6—C5—H5 | 119.9 | C11—C12—C13 | 117.9 (4) |
C4—C5—H5 | 119.9 | C11—C12—H12 | 121.0 |
C5—C6—C1 | 117.1 (3) | C13—C12—H12 | 121.0 |
C5—C6—C8 | 120.0 (3) | C14—C13—C12 | 124.7 (3) |
C1—C6—C8 | 122.9 (3) | C14—C13—H13 | 117.6 |
C4—C7—H7A | 109.5 | C12—C13—H13 | 117.6 |
C4—C7—H7B | 109.5 | C15—C14—C13 | 117.0 (4) |
H7A—C7—H7B | 109.5 | C15—C14—H14 | 121.5 |
C4—C7—H7C | 109.5 | C13—C14—H14 | 121.5 |
H7A—C7—H7C | 109.5 | C14—C15—C10 | 119.1 (4) |
H7B—C7—H7C | 109.5 | C14—C15—H15 | 120.5 |
O2—C8—C6 | 118.6 (3) | C10—C15—H15 | 120.5 |
O1—C1—C2—C3 | −178.7 (4) | C5—C6—C8—C9 | 0.1 (6) |
C6—C1—C2—C3 | 1.1 (7) | C1—C6—C8—C9 | −179.2 (3) |
C1—C2—C3—C4 | −0.2 (7) | O2—C8—C9—C10 | −11.1 (6) |
C2—C3—C4—C5 | −0.8 (7) | C6—C8—C9—C10 | 169.2 (3) |
C2—C3—C4—C7 | 178.9 (4) | C8—C9—C10—C11 | −83.9 (4) |
C3—C4—C5—C6 | 0.8 (6) | C8—C9—C10—C15 | 97.4 (4) |
C7—C4—C5—C6 | −178.9 (4) | C15—C10—C11—C12 | −0.2 (6) |
C4—C5—C6—C1 | 0.1 (6) | C9—C10—C11—C12 | −178.9 (4) |
C4—C5—C6—C8 | −179.3 (4) | C10—C11—C12—C13 | 0.0 (6) |
O1—C1—C6—C5 | 178.7 (4) | C11—C12—C13—C14 | 0.3 (7) |
C2—C1—C6—C5 | −1.1 (6) | C12—C13—C14—C15 | −0.3 (6) |
O1—C1—C6—C8 | −1.9 (6) | C13—C14—C15—C10 | 0.1 (5) |
C2—C1—C6—C8 | 178.3 (4) | C11—C10—C15—C14 | 0.2 (5) |
C5—C6—C8—O2 | −179.5 (4) | C9—C10—C15—C14 | 178.8 (3) |
C1—C6—C8—O2 | 1.1 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.85 | 2.559 (3) | 144 |
O1—H1···C7i | 0.82 | 2.67 | 3.093 (4) | 114 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C15H14O2 |
Mr | 226.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 8.2951 (10), 18.010 (2), 8.9186 (10) |
β (°) | 114.103 (4) |
V (Å3) | 1216.2 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.24 × 0.18 |
Data collection | |
Diffractometer | Bruker APEX II CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.975, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12849, 2115, 1303 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.242, 1.01 |
No. of reflections | 2115 |
No. of parameters | 157 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.20 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.851 | 2.559 (3) | 143.79 |
O1—H1···C7i | 0.82 | 2.670 | 3.093 (4) | 113.9 |
Symmetry code: (i) x−1, y, z. |
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Benzophenones and related compounds have a wide variety of applications, in particular as biologically active compounds, which exhibit anti-inflammatory (Khanum et al., 2004), antifungal, antibacterial and anticancer activities·As an extension of work on the structural characterization of Benzophenone derivatives,the title compound, (I), was synthesized and its crystal structure is reported here.
The molecule of (I) is non-planar (Fig. 1). The dihedral angle between the two aromatic rings is 87.98 (13)°. The crystal structure is stabilized by intramolecular O—H···O hydrogen bonds and intermolecular O—H···C contacts together with C—H···π(arene) contacts and π···π stacking interactions, (Table 1, Fig. 2).