organic compounds
1-(2′,4′-Difluorobiphenyl-4-yl)ethanone
aInstitute of Coordination Catalysis, Yichun University, Yichun, Jiangxi, 336000, People's Republic of China, and bCollege of Chemistry and Bio-engineering, Yichun University, Yichun, Jiangxi, 336000, People's Republic of China
*Correspondence e-mail: zhong_dichang@yahoo.com.cn
In the 14H10F2O, the dihedral angles between the benzene rings in the two crystallographically independent molecules are 46.9 (2) and 47.6 (2)°. The molecules are linked into dimers by C—H⋯F interactions and these dimers are further stacked into columns along the b axis by π–π interactions between the benzene rings [centroid–centroid distance = 3.8221 Å; the dihedral angle between the planes of these rings is 4.87 (2)°]. In addition, C—F⋯π interactions also contribute to the crystal packing (C⋯centroid distance = 3.5919 Å).
of the title compound, CRelated literature
For general background, see: William & Ruyle (1973). For related structures, see:Kuchar et al. (1997); Jegorov et al. (1995, 1997).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536808028596/nc2113sup1.cif
contains datablocks gmp, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808028596/nc2113Isup2.hkl
0.1892 g (1 mmol) 1-(4-bromophenyl)ethanone, 0.2385 g (1.5 mmol) 2,4-difluorophenylboronic acid, 0.2123 g (2 mmol) Na2CO3 and 0.2255 g (1 mmol) Pd(OAc)2 were dissolved in a water-acetone mixture (1:1 v/v; 50 ml). After stirring for 20 min at 308 K, the mixture were extracted using diethylether for four times. Then the resultant diethylether solution were dried over magnesium sulfate and concentrated in vacuo. Well shaped light yellow crystals suitable for X-ray structure analysis were obtained by recrystalling the crude product from ethanol.
Hydrogen atoms attached to carbon atoms were positioned with idealized geometry and were refined isotropic with Uiso(H) = 1.2Ueq(C) using a riding model with C—H = 0.93 Å . The
cannot be determined because no strong atoms are present. Therefore, the Friedel opposites have been merged in the refinement.Data collection: SMART (Bruker, 2004); cell
SMART (Bruker, 2004); data reduction: SHELXTL (Sheldrick, 2008); 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).Fig. 1. Crystal structure of the title compound showing 30% probability displacement ellipsoids and the atom-labeling scheme. |
C14H10F2O | F(000) = 960 |
Mr = 232.22 | Dx = 1.393 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 2398 reflections |
a = 13.092 (7) Å | θ = 2.9–27.5° |
b = 6.102 (3) Å | µ = 0.11 mm−1 |
c = 27.719 (15) Å | T = 293 K |
V = 2214 (2) Å3 | Block, colorless |
Z = 8 | 0.46 × 0.32 × 0.25 mm |
Bruker P4 diffractometer | 2219 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 27.5°, θmin = 2.9° |
ω scans | h = −16→16 |
15497 measured reflections | k = −7→7 |
2576 independent reflections | l = −35→26 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.207 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.135P)2 + 0.237P] where P = (Fo2 + 2Fc2)/3 |
2576 reflections | (Δ/σ)max = 0.045 |
309 parameters | Δρmax = 0.80 e Å−3 |
1 restraint | Δρmin = −0.33 e Å−3 |
C14H10F2O | V = 2214 (2) Å3 |
Mr = 232.22 | Z = 8 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 13.092 (7) Å | µ = 0.11 mm−1 |
b = 6.102 (3) Å | T = 293 K |
c = 27.719 (15) Å | 0.46 × 0.32 × 0.25 mm |
Bruker P4 diffractometer | 2219 reflections with I > 2σ(I) |
15497 measured reflections | Rint = 0.033 |
2576 independent reflections |
R[F2 > 2σ(F2)] = 0.066 | 1 restraint |
wR(F2) = 0.207 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.80 e Å−3 |
2576 reflections | Δρmin = −0.33 e Å−3 |
309 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 | ||
F1 | 0.3975 (2) | 0.4954 (5) | 1.02287 (16) | 0.0734 (10) | |
F2 | 0.7101 (3) | 0.2074 (5) | 0.97293 (14) | 0.0819 (10) | |
O1 | 1.0793 (3) | 0.8318 (7) | 0.83509 (19) | 0.0858 (13) | |
C1 | 0.4849 (4) | 0.5145 (8) | 0.9977 (2) | 0.0567 (13) | |
C2 | 0.5545 (4) | 0.3442 (8) | 0.99906 (18) | 0.0582 (11) | |
H2A | 0.5431 | 0.2190 | 1.0174 | 0.070* | |
C3 | 0.6420 (3) | 0.3703 (7) | 0.97159 (18) | 0.0529 (10) | |
C4 | 0.6630 (3) | 0.5529 (7) | 0.94406 (16) | 0.0456 (8) | |
C5 | 0.5892 (4) | 0.7202 (7) | 0.94479 (17) | 0.0535 (10) | |
H5A | 0.6003 | 0.8463 | 0.9267 | 0.064* | |
C6 | 0.5003 (3) | 0.7029 (8) | 0.9717 (2) | 0.0582 (11) | |
H6A | 0.4525 | 0.8156 | 0.9721 | 0.070* | |
C7 | 0.7577 (3) | 0.5771 (6) | 0.91542 (15) | 0.0451 (8) | |
C8 | 0.7929 (3) | 0.4063 (7) | 0.88590 (18) | 0.0546 (10) | |
H8A | 0.7563 | 0.2761 | 0.8840 | 0.065* | |
C9 | 0.8827 (3) | 0.4311 (7) | 0.85932 (18) | 0.0545 (10) | |
H9A | 0.9059 | 0.3167 | 0.8400 | 0.065* | |
C10 | 0.9376 (3) | 0.6252 (7) | 0.86148 (15) | 0.0497 (9) | |
C11 | 0.9034 (3) | 0.7916 (7) | 0.89094 (19) | 0.0560 (10) | |
H11A | 0.9409 | 0.9208 | 0.8930 | 0.067* | |
C12 | 0.8149 (3) | 0.7706 (7) | 0.91747 (17) | 0.0526 (10) | |
H12A | 0.7931 | 0.8858 | 0.9369 | 0.063* | |
C13 | 1.0342 (4) | 0.6569 (9) | 0.83342 (18) | 0.0613 (12) | |
C14 | 1.0706 (5) | 0.4727 (13) | 0.8035 (3) | 0.089 (2) | |
H14A | 1.1369 | 0.5069 | 0.7908 | 0.133* | |
H14B | 1.0238 | 0.4486 | 0.7774 | 0.133* | |
H14C | 1.0749 | 0.3427 | 0.8229 | 0.133* | |
F3 | 0.3553 (3) | 1.0087 (6) | 1.04498 (16) | 0.0822 (11) | |
F4 | 0.0411 (2) | 1.2848 (4) | 1.09719 (14) | 0.0734 (9) | |
O2 | −0.3281 (3) | 0.6449 (6) | 1.2310 (2) | 0.0821 (11) | |
C15 | 0.2688 (3) | 0.9868 (7) | 1.0722 (2) | 0.0526 (12) | |
C16 | 0.1987 (4) | 1.1521 (7) | 1.07165 (18) | 0.0580 (11) | |
H16 | 0.2096 | 1.2788 | 1.0537 | 0.070* | |
C17 | 0.1123 (3) | 1.1255 (6) | 1.09822 (17) | 0.0500 (9) | |
C18 | 0.0917 (3) | 0.9397 (7) | 1.12637 (16) | 0.0450 (8) | |
C19 | 0.1654 (3) | 0.7758 (7) | 1.12533 (19) | 0.0538 (10) | |
H19 | 0.1547 | 0.6481 | 1.1429 | 0.065* | |
C20 | 0.2550 (4) | 0.7983 (7) | 1.0985 (2) | 0.0578 (10) | |
H20 | 0.3042 | 0.6883 | 1.0985 | 0.069* | |
C21 | −0.0043 (3) | 0.9146 (6) | 1.15438 (15) | 0.0445 (8) | |
C22 | −0.0595 (3) | 0.7189 (7) | 1.15141 (18) | 0.0540 (10) | |
H22 | −0.0362 | 0.6067 | 1.1315 | 0.065* | |
C23 | −0.1482 (3) | 0.6900 (7) | 1.17769 (17) | 0.0537 (10) | |
H23 | −0.1837 | 0.5585 | 1.1752 | 0.064* | |
C24 | −0.1853 (3) | 0.8548 (7) | 1.20778 (15) | 0.0465 (8) | |
C25 | −0.1292 (4) | 1.0488 (8) | 1.21097 (18) | 0.0539 (10) | |
H25 | −0.1518 | 1.1606 | 1.2311 | 0.065* | |
C26 | −0.0409 (3) | 1.0768 (7) | 1.18471 (16) | 0.0506 (9) | |
H26 | −0.0050 | 1.2078 | 1.1874 | 0.061* | |
C27 | −0.2822 (4) | 0.8178 (8) | 1.23485 (19) | 0.0593 (11) | |
C28 | −0.3252 (4) | 0.9976 (11) | 1.2659 (2) | 0.0748 (16) | |
H28A | −0.3950 | 0.9646 | 1.2738 | 0.112* | |
H28B | −0.3223 | 1.1340 | 1.2487 | 0.112* | |
H28C | −0.2860 | 1.0089 | 1.2950 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0568 (18) | 0.080 (2) | 0.084 (2) | −0.0068 (13) | 0.0293 (18) | −0.0080 (16) |
F2 | 0.087 (2) | 0.0644 (18) | 0.094 (2) | 0.0219 (15) | 0.021 (2) | 0.0117 (18) |
O1 | 0.066 (2) | 0.085 (3) | 0.107 (3) | −0.003 (2) | 0.025 (2) | 0.009 (2) |
C1 | 0.056 (3) | 0.063 (3) | 0.051 (3) | −0.0082 (19) | 0.008 (2) | −0.011 (2) |
C2 | 0.065 (3) | 0.058 (2) | 0.051 (2) | −0.005 (2) | 0.009 (2) | −0.003 (2) |
C3 | 0.051 (2) | 0.049 (2) | 0.059 (3) | 0.0048 (16) | 0.000 (2) | −0.008 (2) |
C4 | 0.0427 (19) | 0.0438 (18) | 0.050 (2) | 0.0015 (16) | −0.0015 (17) | −0.0036 (18) |
C5 | 0.055 (2) | 0.051 (2) | 0.054 (2) | 0.0113 (17) | 0.0037 (19) | 0.005 (2) |
C6 | 0.043 (2) | 0.066 (3) | 0.066 (3) | 0.0130 (18) | 0.004 (2) | −0.004 (2) |
C7 | 0.0453 (19) | 0.0434 (18) | 0.047 (2) | 0.0043 (15) | −0.0014 (16) | −0.0040 (18) |
C8 | 0.052 (2) | 0.048 (2) | 0.064 (3) | −0.0013 (17) | 0.004 (2) | −0.013 (2) |
C9 | 0.055 (2) | 0.055 (2) | 0.053 (2) | 0.005 (2) | 0.008 (2) | −0.009 (2) |
C10 | 0.049 (2) | 0.057 (2) | 0.0430 (19) | 0.0049 (17) | −0.0023 (17) | 0.0005 (19) |
C11 | 0.052 (2) | 0.051 (2) | 0.065 (3) | −0.0007 (18) | 0.004 (2) | 0.002 (2) |
C12 | 0.055 (2) | 0.0459 (19) | 0.057 (2) | 0.0044 (17) | 0.008 (2) | −0.006 (2) |
C13 | 0.055 (2) | 0.071 (3) | 0.059 (3) | 0.009 (2) | 0.004 (2) | 0.016 (2) |
C14 | 0.068 (4) | 0.107 (4) | 0.091 (5) | −0.005 (3) | 0.036 (4) | −0.008 (4) |
F3 | 0.070 (2) | 0.090 (2) | 0.086 (3) | −0.0063 (16) | 0.028 (2) | −0.0042 (19) |
F4 | 0.0778 (19) | 0.0526 (13) | 0.090 (2) | 0.0200 (13) | 0.0111 (16) | 0.0100 (15) |
O2 | 0.064 (2) | 0.073 (2) | 0.109 (3) | −0.0153 (18) | 0.018 (2) | 0.004 (2) |
C15 | 0.039 (2) | 0.063 (2) | 0.056 (3) | −0.0044 (16) | 0.009 (2) | −0.007 (2) |
C16 | 0.066 (3) | 0.050 (2) | 0.058 (2) | −0.0070 (19) | 0.004 (2) | −0.001 (2) |
C17 | 0.052 (2) | 0.0434 (19) | 0.055 (2) | 0.0069 (15) | 0.0025 (19) | −0.0022 (18) |
C18 | 0.0430 (19) | 0.0475 (19) | 0.044 (2) | 0.0043 (16) | 0.0007 (16) | −0.0034 (18) |
C19 | 0.045 (2) | 0.051 (2) | 0.065 (3) | 0.0059 (17) | 0.0014 (19) | 0.002 (2) |
C20 | 0.048 (2) | 0.061 (2) | 0.065 (3) | 0.0073 (19) | 0.006 (2) | −0.005 (2) |
C21 | 0.0419 (18) | 0.0474 (19) | 0.044 (2) | 0.0023 (15) | −0.0027 (16) | −0.0017 (18) |
C22 | 0.057 (2) | 0.0421 (19) | 0.063 (3) | 0.0021 (16) | 0.002 (2) | −0.0096 (19) |
C23 | 0.051 (2) | 0.048 (2) | 0.062 (3) | −0.0059 (16) | −0.0004 (19) | −0.0085 (19) |
C24 | 0.0408 (18) | 0.0514 (19) | 0.047 (2) | 0.0007 (15) | −0.0013 (17) | 0.0041 (17) |
C25 | 0.052 (2) | 0.057 (2) | 0.053 (2) | 0.001 (2) | 0.0037 (19) | −0.013 (2) |
C26 | 0.0461 (19) | 0.050 (2) | 0.055 (2) | −0.0055 (16) | 0.0019 (18) | −0.0084 (19) |
C27 | 0.050 (2) | 0.069 (3) | 0.058 (3) | −0.0011 (19) | 0.000 (2) | 0.002 (2) |
C28 | 0.070 (3) | 0.094 (4) | 0.060 (3) | −0.005 (3) | 0.025 (3) | −0.006 (3) |
F1—C1 | 1.345 (6) | F3—C15 | 1.366 (6) |
F2—C3 | 1.335 (5) | F4—C17 | 1.347 (5) |
O1—C13 | 1.221 (7) | O2—C27 | 1.219 (6) |
C1—C2 | 1.382 (7) | C15—C20 | 1.375 (7) |
C1—C6 | 1.372 (8) | C15—C16 | 1.364 (7) |
C2—C3 | 1.385 (7) | C16—C17 | 1.359 (7) |
C2—H2A | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.378 (6) | C17—C18 | 1.402 (6) |
C4—C5 | 1.407 (6) | C18—C19 | 1.390 (5) |
C4—C7 | 1.479 (6) | C18—C21 | 1.486 (5) |
C5—C6 | 1.386 (6) | C19—C20 | 1.396 (6) |
C5—H5A | 0.9300 | C19—H19 | 0.9300 |
C6—H6A | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.403 (5) | C21—C26 | 1.384 (5) |
C7—C12 | 1.399 (6) | C21—C22 | 1.398 (5) |
C8—C9 | 1.395 (6) | C22—C23 | 1.383 (6) |
C8—H8A | 0.9300 | C22—H22 | 0.9300 |
C9—C10 | 1.387 (6) | C23—C24 | 1.394 (6) |
C9—H9A | 0.9300 | C23—H23 | 0.9300 |
C10—C11 | 1.377 (6) | C24—C25 | 1.396 (6) |
C10—C13 | 1.497 (6) | C24—C27 | 1.491 (6) |
C11—C12 | 1.378 (6) | C25—C26 | 1.377 (6) |
C11—H11A | 0.9300 | C25—H25 | 0.9300 |
C12—H12A | 0.9300 | C26—H26 | 0.9300 |
C13—C14 | 1.476 (9) | C27—C28 | 1.504 (8) |
C14—H14A | 0.9600 | C28—H28A | 0.9600 |
C14—H14B | 0.9600 | C28—H28B | 0.9600 |
C14—H14C | 0.9600 | C28—H28C | 0.9600 |
F1—C1—C2 | 118.8 (5) | C20—C15—F3 | 118.9 (4) |
F1—C1—C6 | 118.0 (4) | C20—C15—C16 | 122.4 (4) |
C2—C1—C6 | 123.2 (5) | F3—C15—C16 | 118.7 (5) |
C1—C2—C3 | 116.4 (5) | C17—C16—C15 | 117.8 (4) |
C1—C2—H2A | 121.8 | C17—C16—H16 | 121.1 |
C3—C2—H2A | 121.8 | C15—C16—H16 | 121.1 |
F2—C3—C4 | 118.9 (4) | F4—C17—C16 | 118.6 (4) |
F2—C3—C2 | 116.9 (4) | F4—C17—C18 | 117.6 (4) |
C4—C3—C2 | 124.2 (4) | C16—C17—C18 | 123.9 (4) |
C3—C4—C5 | 116.2 (4) | C19—C18—C17 | 116.0 (4) |
C3—C4—C7 | 123.1 (4) | C19—C18—C21 | 121.6 (4) |
C5—C4—C7 | 120.7 (4) | C17—C18—C21 | 122.4 (3) |
C6—C5—C4 | 122.0 (4) | C18—C19—C20 | 121.6 (4) |
C6—C5—H5A | 119.0 | C18—C19—H19 | 119.2 |
C4—C5—H5A | 119.0 | C20—C19—H19 | 119.2 |
C1—C6—C5 | 118.0 (4) | C15—C20—C19 | 118.4 (4) |
C1—C6—H6A | 121.0 | C15—C20—H20 | 120.8 |
C5—C6—H6A | 121.0 | C19—C20—H20 | 120.8 |
C8—C7—C12 | 118.3 (4) | C26—C21—C22 | 117.9 (4) |
C8—C7—C4 | 120.9 (4) | C26—C21—C18 | 122.4 (3) |
C12—C7—C4 | 120.7 (4) | C22—C21—C18 | 119.6 (4) |
C9—C8—C7 | 120.3 (4) | C23—C22—C21 | 120.8 (4) |
C9—C8—H8A | 119.8 | C23—C22—H22 | 119.6 |
C7—C8—H8A | 119.8 | C21—C22—H22 | 119.6 |
C10—C9—C8 | 120.4 (4) | C22—C23—C24 | 121.1 (4) |
C10—C9—H9A | 119.8 | C22—C23—H23 | 119.5 |
C8—C9—H9A | 119.8 | C24—C23—H23 | 119.5 |
C11—C10—C9 | 119.2 (4) | C23—C24—C25 | 117.8 (4) |
C11—C10—C13 | 119.2 (4) | C23—C24—C27 | 119.2 (4) |
C9—C10—C13 | 121.7 (4) | C25—C24—C27 | 123.0 (4) |
C12—C11—C10 | 121.4 (4) | C26—C25—C24 | 120.9 (4) |
C12—C11—H11A | 119.3 | C26—C25—H25 | 119.5 |
C10—C11—H11A | 119.3 | C24—C25—H25 | 119.5 |
C11—C12—C7 | 120.5 (4) | C25—C26—C21 | 121.5 (4) |
C11—C12—H12A | 119.8 | C25—C26—H26 | 119.2 |
C7—C12—H12A | 119.8 | C21—C26—H26 | 119.2 |
O1—C13—C14 | 122.0 (5) | O2—C27—C24 | 120.4 (5) |
O1—C13—C10 | 120.1 (5) | O2—C27—C28 | 119.8 (5) |
C14—C13—C10 | 117.8 (5) | C24—C27—C28 | 119.8 (5) |
C13—C14—H14A | 109.5 | C27—C28—H28A | 109.5 |
C13—C14—H14B | 109.5 | C27—C28—H28B | 109.5 |
H14A—C14—H14B | 109.5 | H28A—C28—H28B | 109.5 |
C13—C14—H14C | 109.5 | C27—C28—H28C | 109.5 |
H14A—C14—H14C | 109.5 | H28A—C28—H28C | 109.5 |
H14B—C14—H14C | 109.5 | H28B—C28—H28C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···F2i | 0.93 | 2.46 | 3.369 (6) | 167 |
C22—H22···F4ii | 0.93 | 2.40 | 3.318 (6) | 167 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C14H10F2O |
Mr | 232.22 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 293 |
a, b, c (Å) | 13.092 (7), 6.102 (3), 27.719 (15) |
V (Å3) | 2214 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.46 × 0.32 × 0.25 |
Data collection | |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15497, 2576, 2219 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.207, 1.13 |
No. of reflections | 2576 |
No. of parameters | 309 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.80, −0.33 |
Computer programs: SMART (Bruker, 2004), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···F2i | 0.93 | 2.46 | 3.369 (6) | 167 |
C22—H22···F4ii | 0.93 | 2.40 | 3.318 (6) | 167 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |
C—F···Cga | F···Cg | C···Cg | γb | C—F···Cg |
C1—F1···Cg(C7→C12)iii | 3.8358 | 3.5919 | 27.36 | 69 |
C15—F3···Cg(C21→C26)iv | 3.8814 | 3.5966 | 27.14 | 68 |
Notes: Cga = centre of gravity of the six-membered ring. γb = angle defined by a line connecting centre of gravity of the six-membered ring with H atom and the normal to the six-membered ring. Symmetry codes: (iii) x+1/2, 1-y, z ; (IV) x+1/2, -y, z. |
π···π contacts | Cg···Cg(Å) | αa(°) | βb(°) | Cg···Plane(Å) |
Cg(C1→C6)···Cg(C7→C12)iii | 3.8221 | 4.87 | 27.32 | 3.616 |
Cg(C15→C20)···Cg(C21→C26)iv | 3.8284 | 5.68 | 23.57 | 3.642 |
Notes: αa = angle between planes of two aromatic rings. βb = angle between Cg···Cg line and normal to the plane of the first aromatic ring. Symmetry codes: (iii) x+1/2, 1-y, z ; (IV) x+1/2, -y, z. |
Acknowledgements
The work was supported by the National Natural Science Foundation of China (No. 20763008) and the Key Science & Technology Plan of Yichun City (No. [2006] 56).
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The crystal structure of the title compound was determined as a part of a project on the synthesis of 1-(2',4'-difluorobiphenyl-4-yl)ethanone, which have excellent activity against various bacteria, antifebrile and abirritation (William et al., 1973; Kuchar et al., 1997; Jegorov, Husak et al., 1997; Jegorov, Sedmera et al., 1995). The title compound is an intermediate in this synthesis.
The asymmetric unit of (I) contains two crystallographically indepedent molecules of the same stereochemical configuration (Fig. 1). The dihedral angle between aromatic ring C1-C6 and C7-C12 amount to 46.8 (2) ° and between ring C15-C20 and C21-C26 it is 47.6 (2) ° (Fig. 1). The molecules are connected into dimers via C—H···F interactions (Table 1). There also exist π—π stacking interactions between the benzene rings of adjacent molecules. The distances of the centroids of the rings C1-C6 and C7-C12 as well as rings C15-C20 and C21-C26) amount to 3.8821 and 3.8284 /%A, respectively. In the direction of the b-axis, the molecules shows a herringbone like arrangement.