Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034964/ci2418sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034964/ci2418Isup2.hkl |
CCDC reference: 657825
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.002 Å
- R factor = 0.046
- wR factor = 0.145
- Data-to-parameter ratio = 24.6
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.643 1.000 Tmin(prime) and Tmax expected: 0.942 0.970 RR(prime) = 0.662 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.66
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
For related structures, see: Butcher et al. (2006); Yathirajan et al. (2006, 2007); Fischer et al. (2007); Harrison et al. (2006). For related literature, see: Carlo et al. (1999); Fichou et al. (1988); Goto et al. (1991); Uchida et al. (1998); Zhao et al. (2000); Sarojini et al. (2006).
To a mixture of 1-(3-hydroxyphenyl)ethanone (1.36 g, 0.01 mol) and 4-fluoroacetophenone (1.38 g, 0.01 mol) in ethanol (20 ml), a solution of potassium hydroxide (5%, 5 ml) was added slowly with stirring. The mixture was stirred at room temperature for 6 h. The solid that precipitated was filtered off and washed with cold ethanol, dried and recrystallized from ethanol. X-ray quality crystals were obtained from ethyl acetate by slow evaporation (yield: 80%; m.p. 408–09 K). Analysis found: C 74.30, H 4.51%; C15H11ClO2 requires: C 74.37, H 4.58%.
All H atoms, except H1, were found in a difference map. But all H atoms were refined using a riding model with O—H = 0.83 Å and C—H = 0.94 Å, and with Uiso(H) = 1.19–1.20 Ueq(C,O). Owing to the poor diffraction quality of the crystal, the ratio of observed to unique reflections is low (47%).
Chalcones are known for their anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities. Among several organic compounds reported for non-linear optical (NLO) properties, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. We have synthesized a new chalcone, the title compound. In view of the importance of the title compound, its crystal structure is reported here.
The 3-hydroxyphenyl and 4-fluorophenyl groups of the title molecule (Fig. 1) are coplanar [dihedral angle = 3.11 (8)°] with each other and also with the propyl-2-ketone group, forming torsion angles C8—C9—C10—C11 and C8—C7—C1—C6 of 4.9 (2)° and -1.75 (18)°, respectively.
Intermolecular O—H···O hydrogen bonding interactions (Table 1) involving the hydroxyl group and the carbonyl O atom link the molecules into a chain along the [0 1 0] direction (Fig. 2).
For related structures, see: Butcher et al. (2006); Yathirajan et al. (2006, 2007); Fischer et al. (2007); Harrison et al. (2006). For related literature, see: Carlo et al. (1999); Fichou et al. (1988); Goto et al. (1991); Uchida et al. (1998); Zhao et al. (2000); Sarojini et al. (2006).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C15H11FO2 | F(000) = 504 |
Mr = 242.24 | Dx = 1.342 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5107 reflections |
a = 7.4149 (4) Å | θ = 4.8–32.5° |
b = 11.3162 (6) Å | µ = 0.10 mm−1 |
c = 14.7472 (8) Å | T = 203 K |
β = 104.311 (6)° | Prism, colourless |
V = 1199.01 (11) Å3 | 0.59 × 0.47 × 0.31 mm |
Z = 4 |
Oxford Diffraction Gemini R diffractometer | 4038 independent reflections |
Radiation source: fine-focus sealed tube | 1916 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.5°, θmin = 4.8° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −16→17 |
Tmin = 0.643, Tmax = 1.000 | l = −21→22 |
16754 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0687P)2] where P = (Fo2 + 2Fc2)/3 |
4038 reflections | (Δ/σ)max = 0.001 |
164 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C15H11FO2 | V = 1199.01 (11) Å3 |
Mr = 242.24 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.4149 (4) Å | µ = 0.10 mm−1 |
b = 11.3162 (6) Å | T = 203 K |
c = 14.7472 (8) Å | 0.59 × 0.47 × 0.31 mm |
β = 104.311 (6)° |
Oxford Diffraction Gemini R diffractometer | 4038 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 1916 reflections with I > 2σ(I) |
Tmin = 0.643, Tmax = 1.000 | Rint = 0.042 |
16754 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.25 e Å−3 |
4038 reflections | Δρmin = −0.17 e Å−3 |
164 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 | ||
F | 0.53494 (15) | 0.34667 (10) | −0.46126 (6) | 0.0827 (4) | |
O1 | 0.71674 (13) | 0.81902 (9) | 0.33109 (6) | 0.0491 (3) | |
H1 | 0.6731 | 0.8786 | 0.3507 | 0.059* | |
O2 | 0.83919 (12) | 0.53556 (8) | 0.10376 (6) | 0.0449 (3) | |
C1 | 0.65119 (16) | 0.70409 (10) | 0.09520 (8) | 0.0318 (3) | |
C2 | 0.71346 (16) | 0.71937 (11) | 0.19185 (8) | 0.0339 (3) | |
H2A | 0.7999 | 0.6658 | 0.2270 | 0.041* | |
C3 | 0.65035 (17) | 0.81164 (12) | 0.23650 (8) | 0.0360 (3) | |
C4 | 0.52401 (19) | 0.89189 (12) | 0.18486 (9) | 0.0436 (3) | |
H4A | 0.4812 | 0.9555 | 0.2148 | 0.052* | |
C5 | 0.4616 (2) | 0.87745 (13) | 0.08907 (10) | 0.0488 (4) | |
H5A | 0.3759 | 0.9317 | 0.0543 | 0.059* | |
C6 | 0.52293 (19) | 0.78494 (12) | 0.04362 (9) | 0.0426 (3) | |
H6A | 0.4790 | 0.7762 | −0.0215 | 0.051* | |
C7 | 0.72278 (15) | 0.60043 (10) | 0.05300 (8) | 0.0321 (3) | |
C8 | 0.65602 (16) | 0.57558 (11) | −0.04758 (8) | 0.0327 (3) | |
H8A | 0.5600 | 0.6220 | −0.0841 | 0.039* | |
C9 | 0.72904 (16) | 0.48853 (11) | −0.08792 (9) | 0.0347 (3) | |
H9A | 0.8244 | 0.4445 | −0.0485 | 0.042* | |
C10 | 0.67813 (16) | 0.45384 (11) | −0.18606 (9) | 0.0344 (3) | |
C11 | 0.54868 (19) | 0.51720 (12) | −0.25370 (9) | 0.0427 (3) | |
H11A | 0.4933 | 0.5852 | −0.2358 | 0.051* | |
C12 | 0.5007 (2) | 0.48226 (14) | −0.34577 (10) | 0.0523 (4) | |
H12A | 0.4133 | 0.5252 | −0.3908 | 0.063* | |
C13 | 0.5838 (2) | 0.38287 (15) | −0.37027 (10) | 0.0522 (4) | |
C14 | 0.7107 (2) | 0.31840 (14) | −0.30732 (11) | 0.0514 (4) | |
H14A | 0.7654 | 0.2508 | −0.3263 | 0.062* | |
C15 | 0.75793 (18) | 0.35409 (12) | −0.21479 (10) | 0.0418 (3) | |
H15A | 0.8454 | 0.3101 | −0.1706 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F | 0.1133 (9) | 0.0953 (8) | 0.0383 (6) | 0.0028 (7) | 0.0166 (5) | −0.0175 (5) |
O1 | 0.0562 (6) | 0.0548 (6) | 0.0317 (5) | −0.0022 (5) | 0.0020 (4) | −0.0099 (4) |
O2 | 0.0462 (5) | 0.0447 (5) | 0.0384 (5) | 0.0093 (4) | 0.0005 (4) | 0.0028 (4) |
C1 | 0.0304 (6) | 0.0350 (6) | 0.0298 (6) | −0.0055 (5) | 0.0069 (5) | 0.0015 (5) |
C2 | 0.0295 (6) | 0.0384 (7) | 0.0308 (6) | −0.0058 (5) | 0.0020 (5) | 0.0010 (5) |
C3 | 0.0350 (7) | 0.0418 (7) | 0.0300 (7) | −0.0106 (5) | 0.0057 (5) | −0.0054 (5) |
C4 | 0.0456 (8) | 0.0418 (8) | 0.0424 (8) | 0.0012 (6) | 0.0093 (6) | −0.0070 (6) |
C5 | 0.0557 (9) | 0.0475 (8) | 0.0388 (8) | 0.0148 (7) | 0.0030 (6) | 0.0024 (6) |
C6 | 0.0470 (8) | 0.0464 (8) | 0.0316 (7) | 0.0058 (6) | 0.0046 (6) | 0.0023 (6) |
C7 | 0.0288 (6) | 0.0336 (6) | 0.0335 (6) | −0.0046 (5) | 0.0067 (5) | 0.0035 (5) |
C8 | 0.0306 (6) | 0.0360 (7) | 0.0311 (6) | −0.0016 (5) | 0.0066 (5) | 0.0018 (5) |
C9 | 0.0304 (6) | 0.0378 (7) | 0.0354 (7) | −0.0016 (5) | 0.0073 (5) | 0.0030 (5) |
C10 | 0.0285 (6) | 0.0377 (7) | 0.0382 (7) | −0.0057 (5) | 0.0104 (5) | −0.0024 (5) |
C11 | 0.0442 (7) | 0.0459 (8) | 0.0382 (8) | 0.0042 (6) | 0.0103 (6) | −0.0012 (6) |
C12 | 0.0578 (9) | 0.0619 (10) | 0.0345 (8) | 0.0037 (8) | 0.0062 (7) | 0.0031 (7) |
C13 | 0.0629 (10) | 0.0619 (10) | 0.0328 (8) | −0.0047 (8) | 0.0140 (7) | −0.0086 (7) |
C14 | 0.0573 (9) | 0.0512 (9) | 0.0497 (9) | 0.0007 (7) | 0.0209 (7) | −0.0149 (7) |
C15 | 0.0388 (7) | 0.0414 (8) | 0.0455 (8) | 0.0003 (6) | 0.0107 (6) | −0.0030 (6) |
F—C13 | 1.3635 (16) | C7—C8 | 1.4700 (17) |
O1—C3 | 1.3622 (15) | C8—C9 | 1.3330 (17) |
O1—H1 | 0.83 | C8—H8A | 0.94 |
O2—C7 | 1.2348 (14) | C9—C10 | 1.4564 (17) |
C1—C2 | 1.3962 (16) | C9—H9A | 0.94 |
C1—C6 | 1.4009 (17) | C10—C15 | 1.3884 (18) |
C1—C7 | 1.4861 (17) | C10—C11 | 1.3989 (18) |
C2—C3 | 1.3766 (18) | C11—C12 | 1.3739 (19) |
C2—H2A | 0.94 | C11—H11A | 0.94 |
C3—C4 | 1.3890 (18) | C12—C13 | 1.373 (2) |
C4—C5 | 1.3832 (18) | C12—H12A | 0.94 |
C4—H4A | 0.94 | C13—C14 | 1.359 (2) |
C5—C6 | 1.379 (2) | C14—C15 | 1.3825 (19) |
C5—H5A | 0.94 | C14—H14A | 0.94 |
C6—H6A | 0.94 | C15—H15A | 0.94 |
C3—O1—H1 | 109.5 | C9—C8—H8A | 119.4 |
C2—C1—C6 | 118.83 (11) | C7—C8—H8A | 119.4 |
C2—C1—C7 | 117.59 (11) | C8—C9—C10 | 127.49 (12) |
C6—C1—C7 | 123.58 (11) | C8—C9—H9A | 116.3 |
C3—C2—C1 | 121.10 (11) | C10—C9—H9A | 116.3 |
C3—C2—H2A | 119.4 | C15—C10—C11 | 117.91 (12) |
C1—C2—H2A | 119.4 | C15—C10—C9 | 119.80 (12) |
O1—C3—C2 | 117.18 (11) | C11—C10—C9 | 122.28 (12) |
O1—C3—C4 | 123.05 (12) | C12—C11—C10 | 121.45 (13) |
C2—C3—C4 | 119.77 (12) | C12—C11—H11A | 119.3 |
C5—C4—C3 | 119.51 (13) | C10—C11—H11A | 119.3 |
C5—C4—H4A | 120.2 | C13—C12—C11 | 118.18 (14) |
C3—C4—H4A | 120.2 | C13—C12—H12A | 120.9 |
C6—C5—C4 | 121.25 (13) | C11—C12—H12A | 120.9 |
C6—C5—H5A | 119.4 | C14—C13—F | 118.79 (14) |
C4—C5—H5A | 119.4 | C14—C13—C12 | 122.68 (13) |
C5—C6—C1 | 119.53 (12) | F—C13—C12 | 118.53 (14) |
C5—C6—H6A | 120.2 | C13—C14—C15 | 118.74 (14) |
C1—C6—H6A | 120.2 | C13—C14—H14A | 120.6 |
O2—C7—C8 | 120.57 (11) | C15—C14—H14A | 120.6 |
O2—C7—C1 | 118.94 (11) | C14—C15—C10 | 121.04 (13) |
C8—C7—C1 | 120.49 (10) | C14—C15—H15A | 119.5 |
C9—C8—C7 | 121.27 (11) | C10—C15—H15A | 119.5 |
C6—C1—C2—C3 | 0.27 (18) | C1—C7—C8—C9 | 174.75 (11) |
C7—C1—C2—C3 | −178.49 (11) | C7—C8—C9—C10 | −179.81 (10) |
C1—C2—C3—O1 | 179.23 (10) | C8—C9—C10—C15 | −174.46 (12) |
C1—C2—C3—C4 | −0.65 (19) | C8—C9—C10—C11 | 4.9 (2) |
O1—C3—C4—C5 | −179.26 (12) | C15—C10—C11—C12 | 0.2 (2) |
C2—C3—C4—C5 | 0.6 (2) | C9—C10—C11—C12 | −179.18 (12) |
C3—C4—C5—C6 | −0.2 (2) | C10—C11—C12—C13 | −0.2 (2) |
C4—C5—C6—C1 | −0.2 (2) | C11—C12—C13—C14 | 0.0 (2) |
C2—C1—C6—C5 | 0.15 (19) | C11—C12—C13—F | 179.08 (13) |
C7—C1—C6—C5 | 178.82 (13) | F—C13—C14—C15 | −178.96 (12) |
C2—C1—C7—O2 | −3.07 (16) | C12—C13—C14—C15 | 0.1 (2) |
C6—C1—C7—O2 | 178.24 (11) | C13—C14—C15—C10 | −0.1 (2) |
C2—C1—C7—C8 | 176.94 (10) | C11—C10—C15—C14 | −0.10 (19) |
C6—C1—C7—C8 | −1.75 (18) | C9—C10—C15—C14 | 179.32 (12) |
O2—C7—C8—C9 | −5.25 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.83 | 1.91 | 2.7013 (13) | 159 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H11FO2 |
Mr | 242.24 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 203 |
a, b, c (Å) | 7.4149 (4), 11.3162 (6), 14.7472 (8) |
β (°) | 104.311 (6) |
V (Å3) | 1199.01 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.59 × 0.47 × 0.31 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.643, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16754, 4038, 1916 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.755 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.145, 1.06 |
No. of reflections | 4038 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.17 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.83 | 1.91 | 2.7013 (13) | 159 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
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Chalcones are known for their anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities. Among several organic compounds reported for non-linear optical (NLO) properties, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. We have synthesized a new chalcone, the title compound. In view of the importance of the title compound, its crystal structure is reported here.
The 3-hydroxyphenyl and 4-fluorophenyl groups of the title molecule (Fig. 1) are coplanar [dihedral angle = 3.11 (8)°] with each other and also with the propyl-2-ketone group, forming torsion angles C8—C9—C10—C11 and C8—C7—C1—C6 of 4.9 (2)° and -1.75 (18)°, respectively.
Intermolecular O—H···O hydrogen bonding interactions (Table 1) involving the hydroxyl group and the carbonyl O atom link the molecules into a chain along the [0 1 0] direction (Fig. 2).