The title compound, C
15H
11FO
2, 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
CCDC reference: 621554
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.121
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
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
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
C15H11FO2 | F(000) = 504 |
Mr = 242.24 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/c | Melting point: 441-443 K K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1942 (8) Å | Cell parameters from 6828 reflections |
b = 5.7823 (5) Å | θ = 1.0–28.3° |
c = 23.126 (2) Å | µ = 0.10 mm−1 |
β = 96.398 (2)° | T = 293 K |
V = 1221.78 (18) Å3 | Rod, colorless |
Z = 4 | 0.30 × 0.12 × 0.10 mm |
Data collection top
Bruker SMART CCD diffractometer | 2181 independent reflections |
Radiation source: fine-focus sealed tube | 1830 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 25.2°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→11 |
Tmin = 0.765, Tmax = 0.990 | k = −6→6 |
5802 measured reflections | l = −22→27 |
Refinement top
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)] = 0.043 | H 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 reflections | Δρmax = 0.20 e Å−3 |
168 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.0501 (2) | 0.9073 (3) | 0.17102 (8) | 0.0666 (5) | |
C2 | 0.0824 (4) | 1.0724 (4) | 0.21271 (10) | 0.0912 (8) | |
H2A | 0.0161 | 1.1899 | 0.2181 | 0.109* | |
C3 | 0.2140 (4) | 1.0615 (4) | 0.24637 (11) | 0.1033 (9) | |
H3A | 0.2379 | 1.1717 | 0.2752 | 0.124* | |
C4 | 0.3111 (3) | 0.8879 (5) | 0.23774 (9) | 0.0972 (8) | |
H4A | 0.4004 | 0.8813 | 0.2609 | 0.117* | |
C5 | 0.2777 (2) | 0.7225 (4) | 0.19508 (8) | 0.0743 (6) | |
H5A | 0.3443 | 0.6052 | 0.1901 | 0.089* | |
C6 | 0.14461 (18) | 0.7305 (3) | 0.15950 (7) | 0.0542 (4) | |
C7 | 0.09687 (16) | 0.5585 (3) | 0.11495 (7) | 0.0514 (4) | |
H7A | −0.0039 | 0.5419 | 0.1067 | 0.062* | |
C8 | 0.17710 (15) | 0.4218 (3) | 0.08436 (6) | 0.0460 (4) | |
C9 | 0.33902 (16) | 0.4333 (3) | 0.08568 (7) | 0.0509 (4) | |
C10 | 0.40331 (19) | 0.6303 (3) | 0.06563 (8) | 0.0668 (5) | |
H10A | 0.3449 | 0.7533 | 0.0513 | 0.080* | |
C11 | 0.5532 (2) | 0.6452 (5) | 0.06684 (12) | 0.1018 (9) | |
H11A | 0.5956 | 0.7776 | 0.0532 | 0.122* | |
C12 | 0.6393 (2) | 0.4655 (7) | 0.08802 (14) | 0.1243 (13) | |
H12A | 0.7405 | 0.4765 | 0.0891 | 0.149* | |
C13 | 0.5775 (2) | 0.2685 (6) | 0.10774 (13) | 0.1133 (11) | |
H13A | 0.6370 | 0.1463 | 0.1218 | 0.136* | |
C14 | 0.4263 (2) | 0.2509 (4) | 0.10673 (9) | 0.0753 (6) | |
H14A | 0.3845 | 0.1176 | 0.1201 | 0.090* | |
C15 | 0.09952 (15) | 0.2459 (3) | 0.04521 (6) | 0.0472 (4) | |
O1 | 0.16942 (12) | 0.1057 (2) | 0.01872 (6) | 0.0717 (4) | |
O2 | −0.04128 (12) | 0.2475 (2) | 0.04031 (6) | 0.0713 (4) | |
F1 | −0.08282 (15) | 0.9158 (2) | 0.13944 (6) | 0.0978 (5) | |
H2 | −0.088 (3) | 0.113 (5) | 0.0165 (12) | 0.127 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0868 (13) | 0.0592 (11) | 0.0580 (10) | 0.0030 (9) | 0.0271 (9) | 0.0022 (8) |
C2 | 0.149 (2) | 0.0586 (13) | 0.0740 (13) | 0.0016 (13) | 0.0464 (15) | −0.0106 (10) |
C3 | 0.157 (3) | 0.0842 (17) | 0.0747 (14) | −0.0366 (17) | 0.0397 (16) | −0.0354 (12) |
C4 | 0.1025 (17) | 0.121 (2) | 0.0675 (13) | −0.0311 (15) | 0.0070 (12) | −0.0330 (13) |
C5 | 0.0721 (12) | 0.0883 (14) | 0.0621 (11) | −0.0084 (10) | 0.0062 (9) | −0.0209 (10) |
C6 | 0.0607 (9) | 0.0551 (10) | 0.0491 (8) | −0.0078 (7) | 0.0169 (7) | −0.0049 (7) |
C7 | 0.0432 (8) | 0.0568 (9) | 0.0546 (9) | −0.0024 (7) | 0.0066 (6) | −0.0045 (7) |
C8 | 0.0417 (8) | 0.0481 (8) | 0.0475 (8) | −0.0029 (6) | 0.0022 (6) | −0.0022 (6) |
C9 | 0.0404 (8) | 0.0561 (9) | 0.0554 (9) | −0.0014 (7) | 0.0017 (6) | −0.0184 (7) |
C10 | 0.0573 (10) | 0.0688 (11) | 0.0771 (11) | −0.0145 (8) | 0.0202 (8) | −0.0222 (9) |
C11 | 0.0640 (13) | 0.120 (2) | 0.128 (2) | −0.0384 (14) | 0.0421 (13) | −0.0640 (17) |
C12 | 0.0400 (11) | 0.171 (3) | 0.162 (3) | −0.0117 (16) | 0.0111 (13) | −0.109 (2) |
C13 | 0.0575 (13) | 0.128 (2) | 0.144 (2) | 0.0349 (15) | −0.0336 (14) | −0.0722 (19) |
C14 | 0.0584 (11) | 0.0732 (13) | 0.0887 (13) | 0.0137 (9) | −0.0164 (9) | −0.0238 (10) |
C15 | 0.0392 (7) | 0.0516 (9) | 0.0506 (8) | −0.0027 (6) | 0.0044 (6) | −0.0039 (7) |
O1 | 0.0476 (6) | 0.0754 (9) | 0.0906 (9) | 0.0004 (6) | 0.0005 (6) | −0.0376 (7) |
O2 | 0.0418 (6) | 0.0830 (9) | 0.0887 (9) | −0.0099 (6) | 0.0057 (6) | −0.0314 (7) |
F1 | 0.0999 (10) | 0.1007 (10) | 0.0940 (9) | 0.0415 (7) | 0.0164 (7) | −0.0042 (7) |
Geometric parameters (Å, º) top
C1—F1 | 1.353 (2) | C8—C15 | 1.490 (2) |
C1—C2 | 1.366 (3) | C9—C14 | 1.381 (2) |
C1—C6 | 1.387 (2) | C9—C10 | 1.387 (3) |
C2—C3 | 1.365 (4) | C10—C11 | 1.378 (3) |
C2—H2A | 0.9300 | C10—H10A | 0.9300 |
C3—C4 | 1.373 (4) | C11—C12 | 1.364 (4) |
C3—H3A | 0.9300 | C11—H11A | 0.9300 |
C4—C5 | 1.383 (3) | C12—C13 | 1.374 (5) |
C4—H4A | 0.9300 | C12—H12A | 0.9300 |
C5—C6 | 1.397 (3) | C13—C14 | 1.391 (3) |
C5—H5A | 0.9300 | C13—H13A | 0.9300 |
C6—C7 | 1.464 (2) | C14—H14A | 0.9300 |
C7—C8 | 1.336 (2) | C15—O1 | 1.2381 (18) |
C7—H7A | 0.9300 | C15—O2 | 1.2869 (17) |
C8—C9 | 1.487 (2) | O2—H2 | 1.02 (3) |
| | | |
F1—C1—C2 | 117.9 (2) | C9—C8—C15 | 116.95 (12) |
F1—C1—C6 | 118.07 (16) | C14—C9—C10 | 119.50 (16) |
C2—C1—C6 | 124.0 (2) | C14—C9—C8 | 120.98 (16) |
C3—C2—C1 | 118.6 (2) | C10—C9—C8 | 119.51 (15) |
C3—C2—H2A | 120.7 | C11—C10—C9 | 120.5 (2) |
C1—C2—H2A | 120.7 | C11—C10—H10A | 119.8 |
C2—C3—C4 | 120.0 (2) | C9—C10—H10A | 119.8 |
C2—C3—H3A | 120.0 | C12—C11—C10 | 120.0 (3) |
C4—C3—H3A | 120.0 | C12—C11—H11A | 120.0 |
C3—C4—C5 | 120.9 (2) | C10—C11—H11A | 120.0 |
C3—C4—H4A | 119.6 | C11—C12—C13 | 120.4 (2) |
C5—C4—H4A | 119.6 | C11—C12—H12A | 119.8 |
C4—C5—C6 | 120.5 (2) | C13—C12—H12A | 119.8 |
C4—C5—H5A | 119.8 | C12—C13—C14 | 120.3 (2) |
C6—C5—H5A | 119.8 | C12—C13—H13A | 119.9 |
C1—C6—C5 | 115.97 (16) | C14—C13—H13A | 119.9 |
C1—C6—C7 | 119.40 (16) | C9—C14—C13 | 119.4 (2) |
C5—C6—C7 | 124.49 (16) | C9—C14—H14A | 120.3 |
C8—C7—C6 | 129.39 (14) | C13—C14—H14A | 120.3 |
C8—C7—H7A | 115.3 | O1—C15—O2 | 122.27 (14) |
C6—C7—H7A | 115.3 | O1—C15—C8 | 120.53 (13) |
C7—C8—C9 | 124.98 (13) | O2—C15—C8 | 117.21 (13) |
C7—C8—C15 | 118.06 (13) | C15—O2—H2 | 113.4 (15) |
| | | |
F1—C1—C2—C3 | 177.7 (2) | C15—C8—C9—C14 | −65.2 (2) |
C6—C1—C2—C3 | −1.7 (3) | C7—C8—C9—C10 | −64.2 (2) |
C1—C2—C3—C4 | 0.4 (4) | C15—C8—C9—C10 | 114.99 (16) |
C2—C3—C4—C5 | 0.1 (4) | C14—C9—C10—C11 | −0.2 (3) |
C3—C4—C5—C6 | 0.6 (3) | C8—C9—C10—C11 | 179.55 (16) |
F1—C1—C6—C5 | −177.04 (16) | C9—C10—C11—C12 | −0.2 (3) |
C2—C1—C6—C5 | 2.3 (3) | C10—C11—C12—C13 | 0.6 (4) |
F1—C1—C6—C7 | −1.2 (2) | C11—C12—C13—C14 | −0.5 (4) |
C2—C1—C6—C7 | 178.14 (17) | C10—C9—C14—C13 | 0.3 (3) |
C4—C5—C6—C1 | −1.7 (3) | C8—C9—C14—C13 | −179.47 (17) |
C4—C5—C6—C7 | −177.32 (18) | C12—C13—C14—C9 | 0.1 (3) |
C1—C6—C7—C8 | 157.25 (17) | C7—C8—C15—O1 | −175.51 (15) |
C5—C6—C7—C8 | −27.3 (3) | C9—C8—C15—O1 | 5.3 (2) |
C6—C7—C8—C9 | −6.3 (3) | C7—C8—C15—O2 | 4.7 (2) |
C6—C7—C8—C15 | 174.55 (15) | C9—C8—C15—O2 | −174.55 (14) |
C7—C8—C9—C14 | 115.59 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 1.02 (3) | 1.64 (3) | 2.6579 (17) | 177 (3) |
Symmetry code: (i) −x, −y, −z. |