Literature DB >> 21581566

3-Fluoro-N-(3-fluoro-benzo-yl)-N-(2-pyrid-yl)benzamide.

John F Gallagher, Katie Donnelly, Alan J Lough.   

Abstract

The title compound, C(19)H(12)F(2)N(2)O(2), a 2:1 product of the reaction of 3-fluoro-benzoyl-chloride and 2-amino-pyridine crystallizes with a disordered 3-fluoro-benzene ring adopting two conformations [ratio of occupancies 0.959 (4):0.041 (4)]. In the crystal structure, there are no classical hydrogen bonds and inter-actions comprise C-H⋯O in the form 2(C-H)⋯O=C [with motif R(2) (1)(5)]; C-H⋯π(arene) inter-actions are also present.

Entities:  

Year:  2008        PMID： 21581566      PMCID： PMC2968027          DOI： 10.1107/S1600536808041093

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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

C19H12F2N2O2 M = 338.31 Triclinic, a = 5.4932 (4) Å b = 8.1549 (5) Å c = 17.9205 (15) Å α = 78.081 (4)° β = 89.588 (3)° γ = 76.693 (3)° V = 763.69 (10) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 150 (1) K 0.34 × 0.30 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.873, T max = 0.992 5197 measured reflections 3422 independent reflections 1966 reflections with I > 2σ(I) R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.167 S = 1.04 3422 reflections 236 parameters 5 restraints H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.32 e Å−3 Data collection: KappaCCD Server Software (Nonius, 1997 ▶); cell refinement: 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041093/tk2338sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041093/tk2338Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H12F2N2O2Z = 2
Mr = 338.31F(000) = 348
Triclinic, P1Dx = 1.471 Mg m−3
Hall symbol: -P 1Melting point: 403 K
a = 5.4932 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1549 (5) ÅCell parameters from 2910 reflections
c = 17.9205 (15) Åθ = 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) Å30.34 × 0.30 × 0.12 mm
Nonius KappaCCD diffractometer3422 independent reflections
Radiation source: fine-focus sealed X-ray tube1966 reflections with I > 2σ(I)
graphiteRint = 0.043
φ, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)h = −7→7
Tmin = 0.873, Tmax = 0.992k = −10→10
5197 measured reflectionsl = −20→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0816P)2] where P = (Fo2 + 2Fc2)/3
3422 reflections(Δ/σ)max < 0.001
236 parametersΔρmax = 0.26 e Å−3
5 restraintsΔρmin = −0.32 e Å−3
xyzUiso*/UeqOcc. (<1)
F131.4634 (3)0.23528 (17)0.51411 (9)0.0438 (4)
F330.7405 (3)0.6582 (2)−0.04453 (9)0.0534 (6)0.959 (4)
F350.085 (3)0.975 (3)0.064 (3)0.072 (17)0.041 (4)
O11.0215 (3)0.83326 (19)0.37748 (10)0.0389 (5)
C10.9639 (4)0.7323 (3)0.34430 (14)0.0268 (6)
C111.0136 (4)0.5439 (3)0.37798 (13)0.0247 (5)
C121.2170 (4)0.4755 (3)0.42993 (14)0.0283 (6)
C131.2672 (4)0.3023 (3)0.46246 (14)0.0302 (6)
C141.1272 (5)0.1930 (3)0.44586 (14)0.0316 (6)
C150.9220 (5)0.2637 (3)0.39557 (14)0.0310 (6)
C160.8640 (4)0.4374 (3)0.36223 (14)0.0285 (6)
N10.8296 (4)0.7932 (2)0.27278 (11)0.0252 (5)
C210.7380 (4)0.9785 (3)0.25150 (13)0.0232 (5)
N220.8718 (4)1.0596 (2)0.20067 (11)0.0282 (5)
C230.7874 (4)1.2313 (3)0.17910 (14)0.0293 (6)
C240.5739 (4)1.3220 (3)0.20586 (14)0.0288 (6)
C250.4409 (4)1.2343 (3)0.25976 (14)0.0282 (6)
C260.5261 (4)1.0580 (3)0.28380 (14)0.0279 (6)
O21.0823 (3)0.5907 (2)0.21749 (10)0.0357 (5)
C20.8926 (4)0.7035 (3)0.21272 (13)0.0259 (5)
C310.7138 (4)0.7490 (3)0.14525 (13)0.0256 (5)
C320.8076 (5)0.6859 (3)0.08106 (14)0.0287 (6)
C330.6501 (5)0.7166 (3)0.01795 (15)0.0361 (6)
C340.4039 (5)0.8066 (3)0.01530 (16)0.0381 (7)
C350.3124 (5)0.8666 (3)0.07875 (15)0.0345 (6)
C360.4653 (4)0.8371 (3)0.14401 (14)0.0279 (6)
H121.31850.54660.44260.034*
H141.17010.07330.46820.038*
H150.82000.19210.38380.037*
H160.72120.48440.32840.034*
H230.88011.29330.14350.035*
H240.51831.44290.18770.035*
H250.29431.29420.27970.034*
H260.44180.99370.32130.033*
H320.97640.62320.08120.034*
H330.71340.6742−0.02560.043*0.041 (4)
H340.29980.8267−0.02930.046*
H350.14310.92880.07800.041*0.959 (4)
H360.39930.87750.18780.034*
U11U22U33U12U13U23
F130.0402 (9)0.0387 (8)0.0439 (10)−0.0050 (7)−0.0157 (8)0.0068 (7)
F330.0543 (12)0.0759 (13)0.0333 (11)−0.0060 (9)0.0036 (8)−0.0295 (9)
F350.07 (3)0.06 (3)0.07 (4)−0.02 (3)−0.02 (3)0.01 (2)
O10.0534 (12)0.0265 (9)0.0372 (11)−0.0090 (9)−0.0134 (9)−0.0078 (8)
C10.0250 (13)0.0276 (12)0.0256 (14)−0.0026 (11)−0.0028 (10)−0.0049 (11)
C110.0268 (13)0.0234 (11)0.0226 (13)−0.0030 (10)0.0023 (10)−0.0054 (10)
C120.0295 (13)0.0268 (12)0.0292 (14)−0.0068 (11)−0.0019 (11)−0.0074 (11)
C130.0266 (13)0.0286 (13)0.0302 (15)−0.0014 (10)−0.0038 (11)0.0000 (11)
C140.0370 (15)0.0238 (12)0.0309 (15)−0.0054 (11)0.0038 (12)−0.0008 (11)
C150.0361 (14)0.0275 (13)0.0309 (15)−0.0112 (11)0.0012 (12)−0.0052 (11)
C160.0291 (13)0.0313 (13)0.0248 (14)−0.0048 (11)−0.0019 (11)−0.0072 (11)
N10.0300 (11)0.0192 (9)0.0245 (11)−0.0015 (8)−0.0025 (9)−0.0045 (8)
C210.0257 (13)0.0181 (11)0.0240 (13)−0.0001 (10)−0.0039 (10)−0.0056 (9)
N220.0295 (11)0.0240 (10)0.0310 (12)−0.0053 (9)0.0021 (9)−0.0064 (9)
C230.0322 (14)0.0247 (12)0.0308 (15)−0.0083 (11)0.0012 (11)−0.0033 (11)
C240.0338 (14)0.0187 (11)0.0318 (15)−0.0026 (10)−0.0039 (11)−0.0046 (10)
C250.0304 (13)0.0245 (12)0.0292 (14)−0.0027 (10)−0.0001 (11)−0.0086 (10)
C260.0302 (13)0.0271 (12)0.0267 (14)−0.0074 (11)0.0031 (11)−0.0057 (10)
O20.0382 (10)0.0295 (9)0.0310 (11)0.0069 (8)0.0042 (8)−0.0038 (8)
C20.0322 (14)0.0182 (11)0.0261 (14)−0.0032 (10)0.0054 (11)−0.0050 (10)
C310.0322 (13)0.0203 (11)0.0250 (14)−0.0082 (10)0.0020 (11)−0.0044 (10)
C320.0302 (13)0.0240 (12)0.0318 (15)−0.0063 (11)0.0036 (11)−0.0058 (11)
C330.0456 (17)0.0386 (14)0.0284 (15)−0.0139 (13)0.0076 (13)−0.0127 (12)
C340.0413 (16)0.0445 (15)0.0321 (16)−0.0144 (13)−0.0033 (13)−0.0111 (13)
C350.0316 (14)0.0329 (14)0.0400 (17)−0.0085 (12)−0.0006 (12)−0.0090 (12)
C360.0306 (14)0.0257 (12)0.0299 (15)−0.0082 (11)0.0024 (11)−0.0092 (11)
F13—C131.361 (3)C25—C261.381 (3)
F33—C331.353 (3)C31—C321.402 (3)
F35—C351.347 (5)C31—C361.387 (3)
O1—C11.207 (2)C32—C331.374 (3)
C1—N11.420 (3)C33—C341.378 (4)
O2—C21.211 (3)C34—C351.376 (4)
C2—C311.493 (3)C35—C361.391 (3)
N1—C21.420 (3)C12—H120.9500
N1—C211.448 (3)C14—H140.9500
C1—C111.492 (3)C15—H150.9500
C11—C121.393 (3)C16—H160.9500
C11—C161.394 (3)C23—H230.9500
C12—C131.377 (3)C24—H240.9500
C13—C141.379 (3)C25—H250.9500
C14—C151.384 (3)C26—H260.9500
C15—C161.382 (3)C32—H320.9500
C21—N221.331 (3)C33—H330.9500
C21—C261.382 (3)C34—H340.9500
N22—C231.344 (3)C35—H350.9500
C23—C241.375 (3)C36—H360.9500
C24—C251.387 (3)
O1—C1—N1119.86 (19)C32—C33—C34122.6 (2)
O1—C1—C11122.3 (2)C35—C34—C33118.5 (2)
N1—C1—C11117.67 (18)C34—C35—C36120.7 (2)
C12—C11—C16119.5 (2)C31—C36—C35120.1 (2)
C12—C11—C1116.76 (18)C13—C12—H12120.9
C16—C11—C1123.7 (2)C11—C12—H12120.9
C13—C12—C11118.3 (2)C13—C14—H14121.1
F13—C13—C12118.5 (2)C15—C14—H14121.1
F13—C13—C14118.2 (2)C16—C15—H15119.6
C12—C13—C14123.3 (2)C14—C15—H15119.6
C13—C14—C15117.7 (2)C15—C16—H16119.8
C16—C15—C14120.7 (2)C11—C16—H16119.8
C15—C16—C11120.4 (2)N22—C23—H23118.3
C1—N1—C2120.05 (18)C24—C23—H23118.3
C1—N1—C21114.85 (17)C23—C24—H24120.5
C2—N1—C21117.18 (18)C25—C24—H24120.5
N22—C21—C26124.97 (19)C26—C25—H25120.7
N22—C21—N1115.2 (2)C24—C25—H25120.7
C26—C21—N1119.8 (2)C25—C26—H26121.1
C21—N22—C23116.2 (2)C21—C26—H26121.1
N22—C23—C24123.4 (2)C33—C32—H32120.7
C23—C24—C25119.0 (2)C31—C32—H32120.7
C26—C25—C24118.6 (2)C32—C33—H33118.7
C25—C26—C21117.7 (2)C34—C33—H33118.7
O2—C2—N1120.7 (2)C35—C34—H34120.8
O2—C2—C31121.5 (2)C33—C34—H34120.8
N1—C2—C31117.8 (2)C34—C35—H35119.7
C36—C31—C32119.5 (2)C36—C35—H35119.7
C36—C31—C2124.9 (2)C31—C36—H36119.9
C32—C31—C2115.4 (2)C35—C36—H36119.9
C33—C32—C31118.6 (2)
O1—C1—C11—C12−27.9 (3)N1—C21—N22—C23178.84 (18)
N1—C1—C11—C12156.2 (2)C21—N22—C23—C24−1.0 (3)
O1—C1—C11—C16149.8 (2)N22—C23—C24—C252.1 (3)
N1—C1—C11—C16−26.1 (3)C23—C24—C25—C26−1.0 (3)
C16—C11—C12—C131.8 (4)C24—C25—C26—C21−1.1 (3)
C1—C11—C12—C13179.6 (2)N22—C21—C26—C252.3 (3)
C11—C12—C13—F13−179.0 (2)N1—C21—C26—C25−177.79 (18)
C11—C12—C13—C140.4 (4)C1—N1—C2—O2−11.0 (3)
F13—C13—C14—C15177.5 (2)C21—N1—C2—O2136.5 (2)
C12—C13—C14—C15−2.0 (4)C1—N1—C2—C31167.05 (19)
C13—C14—C15—C161.3 (4)C21—N1—C2—C31−45.5 (3)
C14—C15—C16—C110.9 (4)O2—C2—C31—C36160.4 (2)
C12—C11—C16—C15−2.5 (4)N1—C2—C31—C36−17.6 (3)
C1—C11—C16—C15179.9 (2)O2—C2—C31—C32−15.4 (3)
O1—C1—N1—C2138.7 (2)N1—C2—C31—C32166.55 (19)
C11—C1—N1—C2−45.3 (3)C36—C31—C32—C331.3 (3)
O1—C1—N1—C21−9.4 (3)C2—C31—C32—C33177.3 (2)
C11—C1—N1—C21166.5 (2)C31—C32—C33—C34−0.1 (3)
C1—N1—C21—N22101.8 (2)C32—C33—C34—C35−0.5 (4)
C2—N1—C21—N22−47.3 (3)C33—C34—C35—C360.1 (4)
C1—N1—C21—C26−78.1 (3)C32—C31—C36—C35−1.7 (3)
C2—N1—C21—C26132.8 (2)C2—C31—C36—C35−177.4 (2)
C26—C21—N22—C23−1.3 (3)C34—C35—C36—C311.1 (3)
D—H···AD—HH···AD···AD—H···A
C24—H24···O2i0.952.533.097 (3)119
C25—H25···O2i0.952.463.063 (3)121
C25—H25···Cg1i0.952.793.606 (3)145
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C24—H24⋯O2i0.952.533.097 (3)119
C25—H25⋯O2i0.952.463.063 (3)121
C25—H25⋯Cg1i0.952.793.606 (3)145

Symmetry code: (i) . Cg1 is the centroid of the C11–C16 benzene ring.

  6 in total

1.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Assembling an isomer grid: the isomorphous 4-, 3- and 2-fluoro-N'-(4-pyridyl)benzamides.

Authors:  Katie Donnelly; John F Gallagher; Alan J Lough
Journal:  Acta Crystallogr C       Date:  2008-05-21       Impact factor: 1.172

4.  An empirical correction for absorption anisotropy.

Authors:  R H Blessing
Journal:  Acta Crystallogr A       Date:  1995-01-01       Impact factor: 2.290

5.  A structural systematic study of three isomers of difluoro-N-(4-pyridyl)benzamide.

Authors:  Joyce McMahon; Frankie P Anderson; John F Gallagher; Alan J Lough
Journal:  Acta Crystallogr C       Date:  2008-08-09       Impact factor: 1.172

6.  2,3-Difluoro-N-(2-pyrid-yl)benzamide.

Authors:  John F Gallagher; Joyce McMahon; Frankie P Anderson; Alan J Lough
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-20
  6 in total
  2 in total

1.  2-Ferrocenyl-N-(2-ferrocenylbenzo-yl)-N-(4-methyl-2-pyrid-yl)benzamide.

Authors:  John F Gallagher; Steven Alley; Alan J Lough
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-02-28

2.  2-Fluoro-N-(2-fluoro-benzo-yl)-N-(2-pyrid-yl)benzamide.

Authors:  John F Gallagher; Katie Donnelly; Alan J Lough
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-02-06
  2 in total

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