organic compounds
3-Fluoro-N-(3-fluorobenzoyl)-N-(2-pyridyl)benzamide
aSchool of Chemical Sciences, Dublin City University, Dublin 9, Ireland, and bDepartment of Chemistry, 80 St George Street, University of Toronto, Toronto, Ontario, Canada M5S 3H6
*Correspondence e-mail: john.gallagher@dcu.ie
The title compound, C19H12F2N2O2, a 2:1 product of the reaction of 3-fluorobenzoylchloride and 2-aminopyridine crystallizes with a disordered 3-fluorobenzene ring adopting two conformations [ratio of occupancies 0.959 (4):0.041 (4)]. In the there are no classical hydrogen bonds and interactions comprise C—H⋯O in the form 2(C—H)⋯O=C [with motif R21(5)]; C—H⋯π(arene) interactions are also present.
Related literature
For background information, see: Donnelly et al. (2008); Gallagher et al. (2008); McMahon et al. (2008); Moody et al. (1998). For a description of the Cambridge Structural Database, see: Allen (2002). For the parent compound, 2-(dibenzoylamino)pyridine, see: Weng et al. (2006). For related structures, see: Usman et al. (2002a,b).
Experimental
Crystal data
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Refinement
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Data collection: KappaCCD Server Software (Nonius, 1997); cell DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PREP8 (Ferguson, 1998).
Supporting information
10.1107/S1600536808041093/tk2338sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808041093/tk2338Isup2.hkl
Compound (I) was synthesized via standard condensation procedures and similar to the related syntheses reported previously (Donnelly et al., 2008; McMahon et al., 2008). Separation of the 1:1 and 2:1 derivatives was undertaken by using flash
Typical organic workup and washing gave the product (I) in modest yield of 25–35% as a 2:1 component of the mixture. Crystals suitable for X-ray diffraction were grown from CHCl3 as colourless blocks over a period of 1–2 weeks and gave a melting point of 401–406 K. The compounds gave clean 1H and 13C NMR spectra in CDC3 and infrared spectra (in CHCl3 solution, and as KBr disks).For (I), m.p. 401–406 K (uncorrected). IR (νC=O cm-1): 1697(s, br), (CHCl3); 1695(s) (KBr).
Molecule (I) crystallized in the triclinic system; 1 (No. 2) assumed and confirmed by the and analysis. In the final stages of it was observed that there was electron density consistent with a partial occupancy F atom in a position expected for a minor orientation (site) of the F33 atom position. This new site only necessitates rotation by 180° about the C2—C31 axis in a group that is not engaged in strong hydrogen bonding.
PThe minor F35 site was treated initially with isotropic displacement values and in the final
cycles was restrained by DFIX values to 1.350 (5) Å, SIMU restraints of 0.2 (F33, F35) and FLAT constraints of 0.1 with the {C31···C36} benzene ring. The final gave site occupancy values of 0.959 (4):0.041 (4). As the major and minor sites for the C6 ring are essentially coincidental it was decided to retain the major orientation with 100% occupancy for use with the restraints.Refinement and disorder analysis: (WGHT, R-factor and residual electron density).
Refinement without disorder gives an R-factor of 0.058 WGHT = 0.0856 0.018, R = 0.058 and +0.40/-0.30.
with F33 at variable occupancy changes site from 1.000 to 0.937. WGHT = 0.082 0.018, R = 0.057 and +0.39/-0.30. Final and treatment of disorder gives an R-factor of 0.057: WGHT = 0.0816 0, R = 0.057 and +0.26/-0.32 [Inclusion of the minor site at F35 using DFIX/SIMU/FLAT restraints].H atoms attached to C atoms were treated as riding with C—H = 0.95 Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: KappaCCD Server Software (Nonius, 1997); cell
DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PREP8 (Ferguson, 1998).C19H12F2N2O2 | Z = 2 |
Mr = 338.31 | F(000) = 348 |
Triclinic, P1 | Dx = 1.471 Mg m−3 |
Hall symbol: -P 1 | Melting point: 403 K |
a = 5.4932 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.1549 (5) Å | Cell parameters from 2910 reflections |
c = 17.9205 (15) Å | θ = 2.6–27.5° |
α = 78.081 (4)° | µ = 0.11 mm−1 |
β = 89.588 (3)° | T = 150 K |
γ = 76.693 (3)° | Block, colourless |
V = 763.69 (10) Å3 | 0.34 × 0.30 × 0.12 mm |
Nonius KappaCCD diffractometer | 3422 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1966 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ϕ, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −7→7 |
Tmin = 0.873, Tmax = 0.992 | k = −10→10 |
5197 measured reflections | l = −20→23 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0816P)2] where P = (Fo2 + 2Fc2)/3 |
3422 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.26 e Å−3 |
5 restraints | Δρmin = −0.32 e Å−3 |
C19H12F2N2O2 | γ = 76.693 (3)° |
Mr = 338.31 | V = 763.69 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.4932 (4) Å | Mo Kα radiation |
b = 8.1549 (5) Å | µ = 0.11 mm−1 |
c = 17.9205 (15) Å | T = 150 K |
α = 78.081 (4)° | 0.34 × 0.30 × 0.12 mm |
β = 89.588 (3)° |
Nonius KappaCCD diffractometer | 3422 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 1966 reflections with I > 2σ(I) |
Tmin = 0.873, Tmax = 0.992 | Rint = 0.043 |
5197 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 5 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.26 e Å−3 |
3422 reflections | Δρmin = −0.32 e Å−3 |
236 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F13 | 1.4634 (3) | 0.23528 (17) | 0.51411 (9) | 0.0438 (4) | |
F33 | 0.7405 (3) | 0.6582 (2) | −0.04453 (9) | 0.0534 (6) | 0.959 (4) |
F35 | 0.085 (3) | 0.975 (3) | 0.064 (3) | 0.072 (17) | 0.041 (4) |
O1 | 1.0215 (3) | 0.83326 (19) | 0.37748 (10) | 0.0389 (5) | |
C1 | 0.9639 (4) | 0.7323 (3) | 0.34430 (14) | 0.0268 (6) | |
C11 | 1.0136 (4) | 0.5439 (3) | 0.37798 (13) | 0.0247 (5) | |
C12 | 1.2170 (4) | 0.4755 (3) | 0.42993 (14) | 0.0283 (6) | |
C13 | 1.2672 (4) | 0.3023 (3) | 0.46246 (14) | 0.0302 (6) | |
C14 | 1.1272 (5) | 0.1930 (3) | 0.44586 (14) | 0.0316 (6) | |
C15 | 0.9220 (5) | 0.2637 (3) | 0.39557 (14) | 0.0310 (6) | |
C16 | 0.8640 (4) | 0.4374 (3) | 0.36223 (14) | 0.0285 (6) | |
N1 | 0.8296 (4) | 0.7932 (2) | 0.27278 (11) | 0.0252 (5) | |
C21 | 0.7380 (4) | 0.9785 (3) | 0.25150 (13) | 0.0232 (5) | |
N22 | 0.8718 (4) | 1.0596 (2) | 0.20067 (11) | 0.0282 (5) | |
C23 | 0.7874 (4) | 1.2313 (3) | 0.17910 (14) | 0.0293 (6) | |
C24 | 0.5739 (4) | 1.3220 (3) | 0.20586 (14) | 0.0288 (6) | |
C25 | 0.4409 (4) | 1.2343 (3) | 0.25976 (14) | 0.0282 (6) | |
C26 | 0.5261 (4) | 1.0580 (3) | 0.28380 (14) | 0.0279 (6) | |
O2 | 1.0823 (3) | 0.5907 (2) | 0.21749 (10) | 0.0357 (5) | |
C2 | 0.8926 (4) | 0.7035 (3) | 0.21272 (13) | 0.0259 (5) | |
C31 | 0.7138 (4) | 0.7490 (3) | 0.14525 (13) | 0.0256 (5) | |
C32 | 0.8076 (5) | 0.6859 (3) | 0.08106 (14) | 0.0287 (6) | |
C33 | 0.6501 (5) | 0.7166 (3) | 0.01795 (15) | 0.0361 (6) | |
C34 | 0.4039 (5) | 0.8066 (3) | 0.01530 (16) | 0.0381 (7) | |
C35 | 0.3124 (5) | 0.8666 (3) | 0.07875 (15) | 0.0345 (6) | |
C36 | 0.4653 (4) | 0.8371 (3) | 0.14401 (14) | 0.0279 (6) | |
H12 | 1.3185 | 0.5466 | 0.4426 | 0.034* | |
H14 | 1.1701 | 0.0733 | 0.4682 | 0.038* | |
H15 | 0.8200 | 0.1921 | 0.3838 | 0.037* | |
H16 | 0.7212 | 0.4844 | 0.3284 | 0.034* | |
H23 | 0.8801 | 1.2933 | 0.1435 | 0.035* | |
H24 | 0.5183 | 1.4429 | 0.1877 | 0.035* | |
H25 | 0.2943 | 1.2942 | 0.2797 | 0.034* | |
H26 | 0.4418 | 0.9937 | 0.3213 | 0.033* | |
H32 | 0.9764 | 0.6232 | 0.0812 | 0.034* | |
H33 | 0.7134 | 0.6742 | −0.0256 | 0.043* | 0.041 (4) |
H34 | 0.2998 | 0.8267 | −0.0293 | 0.046* | |
H35 | 0.1431 | 0.9288 | 0.0780 | 0.041* | 0.959 (4) |
H36 | 0.3993 | 0.8775 | 0.1878 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F13 | 0.0402 (9) | 0.0387 (8) | 0.0439 (10) | −0.0050 (7) | −0.0157 (8) | 0.0068 (7) |
F33 | 0.0543 (12) | 0.0759 (13) | 0.0333 (11) | −0.0060 (9) | 0.0036 (8) | −0.0295 (9) |
F35 | 0.07 (3) | 0.06 (3) | 0.07 (4) | −0.02 (3) | −0.02 (3) | 0.01 (2) |
O1 | 0.0534 (12) | 0.0265 (9) | 0.0372 (11) | −0.0090 (9) | −0.0134 (9) | −0.0078 (8) |
C1 | 0.0250 (13) | 0.0276 (12) | 0.0256 (14) | −0.0026 (11) | −0.0028 (10) | −0.0049 (11) |
C11 | 0.0268 (13) | 0.0234 (11) | 0.0226 (13) | −0.0030 (10) | 0.0023 (10) | −0.0054 (10) |
C12 | 0.0295 (13) | 0.0268 (12) | 0.0292 (14) | −0.0068 (11) | −0.0019 (11) | −0.0074 (11) |
C13 | 0.0266 (13) | 0.0286 (13) | 0.0302 (15) | −0.0014 (10) | −0.0038 (11) | 0.0000 (11) |
C14 | 0.0370 (15) | 0.0238 (12) | 0.0309 (15) | −0.0054 (11) | 0.0038 (12) | −0.0008 (11) |
C15 | 0.0361 (14) | 0.0275 (13) | 0.0309 (15) | −0.0112 (11) | 0.0012 (12) | −0.0052 (11) |
C16 | 0.0291 (13) | 0.0313 (13) | 0.0248 (14) | −0.0048 (11) | −0.0019 (11) | −0.0072 (11) |
N1 | 0.0300 (11) | 0.0192 (9) | 0.0245 (11) | −0.0015 (8) | −0.0025 (9) | −0.0045 (8) |
C21 | 0.0257 (13) | 0.0181 (11) | 0.0240 (13) | −0.0001 (10) | −0.0039 (10) | −0.0056 (9) |
N22 | 0.0295 (11) | 0.0240 (10) | 0.0310 (12) | −0.0053 (9) | 0.0021 (9) | −0.0064 (9) |
C23 | 0.0322 (14) | 0.0247 (12) | 0.0308 (15) | −0.0083 (11) | 0.0012 (11) | −0.0033 (11) |
C24 | 0.0338 (14) | 0.0187 (11) | 0.0318 (15) | −0.0026 (10) | −0.0039 (11) | −0.0046 (10) |
C25 | 0.0304 (13) | 0.0245 (12) | 0.0292 (14) | −0.0027 (10) | −0.0001 (11) | −0.0086 (10) |
C26 | 0.0302 (13) | 0.0271 (12) | 0.0267 (14) | −0.0074 (11) | 0.0031 (11) | −0.0057 (10) |
O2 | 0.0382 (10) | 0.0295 (9) | 0.0310 (11) | 0.0069 (8) | 0.0042 (8) | −0.0038 (8) |
C2 | 0.0322 (14) | 0.0182 (11) | 0.0261 (14) | −0.0032 (10) | 0.0054 (11) | −0.0050 (10) |
C31 | 0.0322 (13) | 0.0203 (11) | 0.0250 (14) | −0.0082 (10) | 0.0020 (11) | −0.0044 (10) |
C32 | 0.0302 (13) | 0.0240 (12) | 0.0318 (15) | −0.0063 (11) | 0.0036 (11) | −0.0058 (11) |
C33 | 0.0456 (17) | 0.0386 (14) | 0.0284 (15) | −0.0139 (13) | 0.0076 (13) | −0.0127 (12) |
C34 | 0.0413 (16) | 0.0445 (15) | 0.0321 (16) | −0.0144 (13) | −0.0033 (13) | −0.0111 (13) |
C35 | 0.0316 (14) | 0.0329 (14) | 0.0400 (17) | −0.0085 (12) | −0.0006 (12) | −0.0090 (12) |
C36 | 0.0306 (14) | 0.0257 (12) | 0.0299 (15) | −0.0082 (11) | 0.0024 (11) | −0.0092 (11) |
F13—C13 | 1.361 (3) | C25—C26 | 1.381 (3) |
F33—C33 | 1.353 (3) | C31—C32 | 1.402 (3) |
F35—C35 | 1.347 (5) | C31—C36 | 1.387 (3) |
O1—C1 | 1.207 (2) | C32—C33 | 1.374 (3) |
C1—N1 | 1.420 (3) | C33—C34 | 1.378 (4) |
O2—C2 | 1.211 (3) | C34—C35 | 1.376 (4) |
C2—C31 | 1.493 (3) | C35—C36 | 1.391 (3) |
N1—C2 | 1.420 (3) | C12—H12 | 0.9500 |
N1—C21 | 1.448 (3) | C14—H14 | 0.9500 |
C1—C11 | 1.492 (3) | C15—H15 | 0.9500 |
C11—C12 | 1.393 (3) | C16—H16 | 0.9500 |
C11—C16 | 1.394 (3) | C23—H23 | 0.9500 |
C12—C13 | 1.377 (3) | C24—H24 | 0.9500 |
C13—C14 | 1.379 (3) | C25—H25 | 0.9500 |
C14—C15 | 1.384 (3) | C26—H26 | 0.9500 |
C15—C16 | 1.382 (3) | C32—H32 | 0.9500 |
C21—N22 | 1.331 (3) | C33—H33 | 0.9500 |
C21—C26 | 1.382 (3) | C34—H34 | 0.9500 |
N22—C23 | 1.344 (3) | C35—H35 | 0.9500 |
C23—C24 | 1.375 (3) | C36—H36 | 0.9500 |
C24—C25 | 1.387 (3) | ||
O1—C1—N1 | 119.86 (19) | C32—C33—C34 | 122.6 (2) |
O1—C1—C11 | 122.3 (2) | C35—C34—C33 | 118.5 (2) |
N1—C1—C11 | 117.67 (18) | C34—C35—C36 | 120.7 (2) |
C12—C11—C16 | 119.5 (2) | C31—C36—C35 | 120.1 (2) |
C12—C11—C1 | 116.76 (18) | C13—C12—H12 | 120.9 |
C16—C11—C1 | 123.7 (2) | C11—C12—H12 | 120.9 |
C13—C12—C11 | 118.3 (2) | C13—C14—H14 | 121.1 |
F13—C13—C12 | 118.5 (2) | C15—C14—H14 | 121.1 |
F13—C13—C14 | 118.2 (2) | C16—C15—H15 | 119.6 |
C12—C13—C14 | 123.3 (2) | C14—C15—H15 | 119.6 |
C13—C14—C15 | 117.7 (2) | C15—C16—H16 | 119.8 |
C16—C15—C14 | 120.7 (2) | C11—C16—H16 | 119.8 |
C15—C16—C11 | 120.4 (2) | N22—C23—H23 | 118.3 |
C1—N1—C2 | 120.05 (18) | C24—C23—H23 | 118.3 |
C1—N1—C21 | 114.85 (17) | C23—C24—H24 | 120.5 |
C2—N1—C21 | 117.18 (18) | C25—C24—H24 | 120.5 |
N22—C21—C26 | 124.97 (19) | C26—C25—H25 | 120.7 |
N22—C21—N1 | 115.2 (2) | C24—C25—H25 | 120.7 |
C26—C21—N1 | 119.8 (2) | C25—C26—H26 | 121.1 |
C21—N22—C23 | 116.2 (2) | C21—C26—H26 | 121.1 |
N22—C23—C24 | 123.4 (2) | C33—C32—H32 | 120.7 |
C23—C24—C25 | 119.0 (2) | C31—C32—H32 | 120.7 |
C26—C25—C24 | 118.6 (2) | C32—C33—H33 | 118.7 |
C25—C26—C21 | 117.7 (2) | C34—C33—H33 | 118.7 |
O2—C2—N1 | 120.7 (2) | C35—C34—H34 | 120.8 |
O2—C2—C31 | 121.5 (2) | C33—C34—H34 | 120.8 |
N1—C2—C31 | 117.8 (2) | C34—C35—H35 | 119.7 |
C36—C31—C32 | 119.5 (2) | C36—C35—H35 | 119.7 |
C36—C31—C2 | 124.9 (2) | C31—C36—H36 | 119.9 |
C32—C31—C2 | 115.4 (2) | C35—C36—H36 | 119.9 |
C33—C32—C31 | 118.6 (2) | ||
O1—C1—C11—C12 | −27.9 (3) | N1—C21—N22—C23 | 178.84 (18) |
N1—C1—C11—C12 | 156.2 (2) | C21—N22—C23—C24 | −1.0 (3) |
O1—C1—C11—C16 | 149.8 (2) | N22—C23—C24—C25 | 2.1 (3) |
N1—C1—C11—C16 | −26.1 (3) | C23—C24—C25—C26 | −1.0 (3) |
C16—C11—C12—C13 | 1.8 (4) | C24—C25—C26—C21 | −1.1 (3) |
C1—C11—C12—C13 | 179.6 (2) | N22—C21—C26—C25 | 2.3 (3) |
C11—C12—C13—F13 | −179.0 (2) | N1—C21—C26—C25 | −177.79 (18) |
C11—C12—C13—C14 | 0.4 (4) | C1—N1—C2—O2 | −11.0 (3) |
F13—C13—C14—C15 | 177.5 (2) | C21—N1—C2—O2 | 136.5 (2) |
C12—C13—C14—C15 | −2.0 (4) | C1—N1—C2—C31 | 167.05 (19) |
C13—C14—C15—C16 | 1.3 (4) | C21—N1—C2—C31 | −45.5 (3) |
C14—C15—C16—C11 | 0.9 (4) | O2—C2—C31—C36 | 160.4 (2) |
C12—C11—C16—C15 | −2.5 (4) | N1—C2—C31—C36 | −17.6 (3) |
C1—C11—C16—C15 | 179.9 (2) | O2—C2—C31—C32 | −15.4 (3) |
O1—C1—N1—C2 | 138.7 (2) | N1—C2—C31—C32 | 166.55 (19) |
C11—C1—N1—C2 | −45.3 (3) | C36—C31—C32—C33 | 1.3 (3) |
O1—C1—N1—C21 | −9.4 (3) | C2—C31—C32—C33 | 177.3 (2) |
C11—C1—N1—C21 | 166.5 (2) | C31—C32—C33—C34 | −0.1 (3) |
C1—N1—C21—N22 | 101.8 (2) | C32—C33—C34—C35 | −0.5 (4) |
C2—N1—C21—N22 | −47.3 (3) | C33—C34—C35—C36 | 0.1 (4) |
C1—N1—C21—C26 | −78.1 (3) | C32—C31—C36—C35 | −1.7 (3) |
C2—N1—C21—C26 | 132.8 (2) | C2—C31—C36—C35 | −177.4 (2) |
C26—C21—N22—C23 | −1.3 (3) | C34—C35—C36—C31 | 1.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···O2i | 0.95 | 2.53 | 3.097 (3) | 119 |
C25—H25···O2i | 0.95 | 2.46 | 3.063 (3) | 121 |
C25—H25···Cg1i | 0.95 | 2.79 | 3.606 (3) | 145 |
Symmetry code: (i) x−1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C19H12F2N2O2 |
Mr | 338.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 5.4932 (4), 8.1549 (5), 17.9205 (15) |
α, β, γ (°) | 78.081 (4), 89.588 (3), 76.693 (3) |
V (Å3) | 763.69 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.34 × 0.30 × 0.12 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.873, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5197, 3422, 1966 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.167, 1.04 |
No. of reflections | 3422 |
No. of parameters | 236 |
No. of restraints | 5 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.32 |
Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PREP8 (Ferguson, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···O2i | 0.95 | 2.53 | 3.097 (3) | 119 |
C25—H25···O2i | 0.95 | 2.46 | 3.063 (3) | 121 |
C25—H25···Cg1i | 0.95 | 2.79 | 3.606 (3) | 145 |
Symmetry code: (i) x−1, y+1, z. |
Footnotes
‡Additional correspondence author, e-mail: alough@chem.utoronto.ca.
Acknowledgements
JFG thanks Dublin City University for grants in aid of undergraduate research. Thanks especially to Mr Damien McGuirk for providing excellent technical support in the undergraduate research laboratories.
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Our group is completing a structural systematic study of fluoro-N'-(pyridyl)benzamide isomers (Donnelly et al., 2008) and we are adding to our research with the analogous difluoro-N-(pyridyl)benzamide series (McMahon et al., 2008) (Scheme 1).
In the chemical synthesis of either the mono- or di-fluoro derivatives and when using the ortho-aminopyridine, two products can be isolated as either the 1:1 or 2:1 benzoyl:pyridine components, and with yields and ratios depending on the reaction conditions. We have reported the structure of the 1:1 derivative, 2,3-difluoro-N-(2-pyridyl)benzamide (Gallagher et al., 2008), and now report a 2:1 relative of this compound, namely 3-fluoro-N'-(3-fluorobenzoyl)-N'-(2-pyridinyl)benzamide (I) (Figs 1 & 2). The parent compound 2-(dibenzoylamino)pyridine has been reported previously (Weng et al., 2006) as well as the compounds N,N-dibenzoyl-4-chloroaniline and 4-acetyl-N,N-dibenzoylphenylamine (Usman et al., 2002a,b).
In the crystal structure of (I), there are no classical hydrogen bonds and the weaker interactions present consist of C—H···O and C—H···π(arene) contacts. An unusual (phenyl)C—H···C=O interaction arises between neighbouring molecules as (C24—H24/C25—H25)···O2=C2i [graph set R21(5)] with O···C distances of 3.062 (3) and 3.097 (3) Å (symmetry code: i = x - 1, y + 1, z), Table 1.
A search of the literature (Allen, 2002) reveals a structure exhibiting a comparable example of hydrogen bonding and is archived in the CSD (as XOXRIL). However, in this structure the interacting molecules are offset with respect to the C=O···C2 moiety in the aromatic C5N ring. A related search yielded POZWUW (Fig. 3) (Moody et al., 1998) and RINXUI which both have relatively symmetrical C=O···C2 distances similar to (I) and form chains along the b axis. In the POZWUW structure the C3/C4···O1ii distances are 3.013 (3) and 3.090 (3) Å, and similar to that in (I) (symmetry code: ii = x, y - 1, z) (Fig. 3).
A related search for C=O···C2 [in C6] yielded 6 compounds in the same range of C···O from 2.0–3.0 Å but most were disordered, with high R-factors and typically had the solvent benzene as the acceptor; these are listed as BARJUZ10, LAYDAQ, MERRIK, OGOPUV, SEDLET, XICFEV (Allen, 2002).