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The title compound, C15H11FO2, is a derivative of α-phenyl­cinnamic acid. The two benzene rings in the mol­ecule are approximately perpendicular to each other. O—H...O hydrogen bonding occurs between mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033435/xu2104sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033435/xu2104Isup2.hkl
Contains datablock I

CCDC reference: 621554

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.121
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

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Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.765 0.990 Tmin(prime) and Tmax expected: 0.971 0.990 RR(prime) = 0.788 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.79 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.01 PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2 - H2 ... 1.02 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

3-(2-fluorophenyl)-2-phenylacrylic acid top
Crystal data top
C15H11FO2F(000) = 504
Mr = 242.24Dx = 1.317 Mg m3
Monoclinic, P21/cMelting point: 441-443 K K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.1942 (8) ÅCell parameters from 6828 reflections
b = 5.7823 (5) Åθ = 1.0–28.3°
c = 23.126 (2) ŵ = 0.10 mm1
β = 96.398 (2)°T = 293 K
V = 1221.78 (18) Å3Rod, colorless
Z = 40.30 × 0.12 × 0.10 mm
Data collection top
Bruker SMART CCD
diffractometer
2181 independent reflections
Radiation source: fine-focus sealed tube1830 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 25.2°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1011
Tmin = 0.765, Tmax = 0.990k = 66
5802 measured reflectionsl = 2227
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)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.05P)2 + 0.3354P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2181 reflectionsΔρmax = 0.20 e Å3
168 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (3)
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
C10.0501 (2)0.9073 (3)0.17102 (8)0.0666 (5)
C20.0824 (4)1.0724 (4)0.21271 (10)0.0912 (8)
H2A0.01611.18990.21810.109*
C30.2140 (4)1.0615 (4)0.24637 (11)0.1033 (9)
H3A0.23791.17170.27520.124*
C40.3111 (3)0.8879 (5)0.23774 (9)0.0972 (8)
H4A0.40040.88130.26090.117*
C50.2777 (2)0.7225 (4)0.19508 (8)0.0743 (6)
H5A0.34430.60520.19010.089*
C60.14461 (18)0.7305 (3)0.15950 (7)0.0542 (4)
C70.09687 (16)0.5585 (3)0.11495 (7)0.0514 (4)
H7A0.00390.54190.10670.062*
C80.17710 (15)0.4218 (3)0.08436 (6)0.0460 (4)
C90.33902 (16)0.4333 (3)0.08568 (7)0.0509 (4)
C100.40331 (19)0.6303 (3)0.06563 (8)0.0668 (5)
H10A0.34490.75330.05130.080*
C110.5532 (2)0.6452 (5)0.06684 (12)0.1018 (9)
H11A0.59560.77760.05320.122*
C120.6393 (2)0.4655 (7)0.08802 (14)0.1243 (13)
H12A0.74050.47650.08910.149*
C130.5775 (2)0.2685 (6)0.10774 (13)0.1133 (11)
H13A0.63700.14630.12180.136*
C140.4263 (2)0.2509 (4)0.10673 (9)0.0753 (6)
H14A0.38450.11760.12010.090*
C150.09952 (15)0.2459 (3)0.04521 (6)0.0472 (4)
O10.16942 (12)0.1057 (2)0.01872 (6)0.0717 (4)
O20.04128 (12)0.2475 (2)0.04031 (6)0.0713 (4)
F10.08282 (15)0.9158 (2)0.13944 (6)0.0978 (5)
H20.088 (3)0.113 (5)0.0165 (12)0.127 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0868 (13)0.0592 (11)0.0580 (10)0.0030 (9)0.0271 (9)0.0022 (8)
C20.149 (2)0.0586 (13)0.0740 (13)0.0016 (13)0.0464 (15)0.0106 (10)
C30.157 (3)0.0842 (17)0.0747 (14)0.0366 (17)0.0397 (16)0.0354 (12)
C40.1025 (17)0.121 (2)0.0675 (13)0.0311 (15)0.0070 (12)0.0330 (13)
C50.0721 (12)0.0883 (14)0.0621 (11)0.0084 (10)0.0062 (9)0.0209 (10)
C60.0607 (9)0.0551 (10)0.0491 (8)0.0078 (7)0.0169 (7)0.0049 (7)
C70.0432 (8)0.0568 (9)0.0546 (9)0.0024 (7)0.0066 (6)0.0045 (7)
C80.0417 (8)0.0481 (8)0.0475 (8)0.0029 (6)0.0022 (6)0.0022 (6)
C90.0404 (8)0.0561 (9)0.0554 (9)0.0014 (7)0.0017 (6)0.0184 (7)
C100.0573 (10)0.0688 (11)0.0771 (11)0.0145 (8)0.0202 (8)0.0222 (9)
C110.0640 (13)0.120 (2)0.128 (2)0.0384 (14)0.0421 (13)0.0640 (17)
C120.0400 (11)0.171 (3)0.162 (3)0.0117 (16)0.0111 (13)0.109 (2)
C130.0575 (13)0.128 (2)0.144 (2)0.0349 (15)0.0336 (14)0.0722 (19)
C140.0584 (11)0.0732 (13)0.0887 (13)0.0137 (9)0.0164 (9)0.0238 (10)
C150.0392 (7)0.0516 (9)0.0506 (8)0.0027 (6)0.0044 (6)0.0039 (7)
O10.0476 (6)0.0754 (9)0.0906 (9)0.0004 (6)0.0005 (6)0.0376 (7)
O20.0418 (6)0.0830 (9)0.0887 (9)0.0099 (6)0.0057 (6)0.0314 (7)
F10.0999 (10)0.1007 (10)0.0940 (9)0.0415 (7)0.0164 (7)0.0042 (7)
Geometric parameters (Å, º) top
C1—F11.353 (2)C8—C151.490 (2)
C1—C21.366 (3)C9—C141.381 (2)
C1—C61.387 (2)C9—C101.387 (3)
C2—C31.365 (4)C10—C111.378 (3)
C2—H2A0.9300C10—H10A0.9300
C3—C41.373 (4)C11—C121.364 (4)
C3—H3A0.9300C11—H11A0.9300
C4—C51.383 (3)C12—C131.374 (5)
C4—H4A0.9300C12—H12A0.9300
C5—C61.397 (3)C13—C141.391 (3)
C5—H5A0.9300C13—H13A0.9300
C6—C71.464 (2)C14—H14A0.9300
C7—C81.336 (2)C15—O11.2381 (18)
C7—H7A0.9300C15—O21.2869 (17)
C8—C91.487 (2)O2—H21.02 (3)
F1—C1—C2117.9 (2)C9—C8—C15116.95 (12)
F1—C1—C6118.07 (16)C14—C9—C10119.50 (16)
C2—C1—C6124.0 (2)C14—C9—C8120.98 (16)
C3—C2—C1118.6 (2)C10—C9—C8119.51 (15)
C3—C2—H2A120.7C11—C10—C9120.5 (2)
C1—C2—H2A120.7C11—C10—H10A119.8
C2—C3—C4120.0 (2)C9—C10—H10A119.8
C2—C3—H3A120.0C12—C11—C10120.0 (3)
C4—C3—H3A120.0C12—C11—H11A120.0
C3—C4—C5120.9 (2)C10—C11—H11A120.0
C3—C4—H4A119.6C11—C12—C13120.4 (2)
C5—C4—H4A119.6C11—C12—H12A119.8
C4—C5—C6120.5 (2)C13—C12—H12A119.8
C4—C5—H5A119.8C12—C13—C14120.3 (2)
C6—C5—H5A119.8C12—C13—H13A119.9
C1—C6—C5115.97 (16)C14—C13—H13A119.9
C1—C6—C7119.40 (16)C9—C14—C13119.4 (2)
C5—C6—C7124.49 (16)C9—C14—H14A120.3
C8—C7—C6129.39 (14)C13—C14—H14A120.3
C8—C7—H7A115.3O1—C15—O2122.27 (14)
C6—C7—H7A115.3O1—C15—C8120.53 (13)
C7—C8—C9124.98 (13)O2—C15—C8117.21 (13)
C7—C8—C15118.06 (13)C15—O2—H2113.4 (15)
F1—C1—C2—C3177.7 (2)C15—C8—C9—C1465.2 (2)
C6—C1—C2—C31.7 (3)C7—C8—C9—C1064.2 (2)
C1—C2—C3—C40.4 (4)C15—C8—C9—C10114.99 (16)
C2—C3—C4—C50.1 (4)C14—C9—C10—C110.2 (3)
C3—C4—C5—C60.6 (3)C8—C9—C10—C11179.55 (16)
F1—C1—C6—C5177.04 (16)C9—C10—C11—C120.2 (3)
C2—C1—C6—C52.3 (3)C10—C11—C12—C130.6 (4)
F1—C1—C6—C71.2 (2)C11—C12—C13—C140.5 (4)
C2—C1—C6—C7178.14 (17)C10—C9—C14—C130.3 (3)
C4—C5—C6—C11.7 (3)C8—C9—C14—C13179.47 (17)
C4—C5—C6—C7177.32 (18)C12—C13—C14—C90.1 (3)
C1—C6—C7—C8157.25 (17)C7—C8—C15—O1175.51 (15)
C5—C6—C7—C827.3 (3)C9—C8—C15—O15.3 (2)
C6—C7—C8—C96.3 (3)C7—C8—C15—O24.7 (2)
C6—C7—C8—C15174.55 (15)C9—C8—C15—O2174.55 (14)
C7—C8—C9—C14115.59 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i1.02 (3)1.64 (3)2.6579 (17)177 (3)
Symmetry code: (i) x, y, z.
 

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