2,3-Difluoro-N-(2-pyrid­yl)benzamide

Gallagher, J.F.; McMahon, J.; Anderson, F.P.; Lough, A.J.

doi:10.1107/S1600536808038269

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2394

doi:10.1107/S1600536808038269

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2,3-Difluoro-N-(2-pyridyl)benzamide

John F. Gallagher,^a ^* Joyce McMahon,^a Frankie P. Anderson ^b and Alan J. Lough ^c ‡

^aSchool of Chemical Sciences, Dublin City University, Dublin 9, Ireland, ^bSchool of Chemical Sciences, National Institute for Cellular Biotechnology, Dublin City University, Dublin 9, Ireland, and ^cDepartment of Chemistry, 80 St George Street, University of Toronto, Toronto, Ontario, Canada M5S 3H6
^*Correspondence e-mail: john.gallagher@dcu.ie

(Received 14 November 2008; accepted 17 November 2008; online 20 November 2008)

The title compound, C₁₂H₈F₂N₂O, crystallizes with two independent molecules in the asymmetric unit. The independent molecules differ slightly in conformation; the dihedral angles between the benzene and pyridine rings are 51.58 (5) and 49.97 (4)°. In the crystal structure, molecules aggregate via N—H⋯N_pyridine interactions as hydrogen-bonded dimers with the structural motif R₂²(8), and these dimers are linked via C—H⋯O interactions to form a supramolecular chain.

Related literature

For background information, see: Chopra & Row (2008 ); Donnelly et al. (2008 ); Gelbrich et al. (2007 ); McMahon et al. (2008 ). For a related structure, see: Forbes et al. (2001 ). For the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₂H₈F₂N₂O
M_r = 234.20
Monoclinic, P 2₁ /n
a = 11.8515 (4) Å
b = 9.0554 (2) Å
c = 20.1075 (7) Å
β = 100.2620 (15)°
V = 2123.42 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 150 (1) K
0.26 × 0.20 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.875, T_max = 0.981
5113 measured reflections
4803 independent reflections
3170 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.128
S = 1.04
4803 reflections
316 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯N22B	0.894 (19)	2.076 (19)	2.968 (2)	175.9 (16)
N1B—H1B⋯N22A	0.90 (2)	2.10 (2)	2.999 (2)	175.4 (17)
C25B—H25B⋯O1Aⁱ	0.95	2.48	3.379 (2)	159
C25A—H25A⋯O1Bⁱⁱ	0.95	2.67	3.542 (2)	153
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038269/tk2329sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038269/tk2329Isup2.hkl

checkCIF report

Comment top

Our group is completing a structural systematic study of fluoro-N'-(pyridyl)benzamide isomers (Donnelly et al., 2008) and are adding to our research with the analogous difluoro-N-(pyridyl)benzamide series (McMahon et al., 2008) (Scheme 1). A total of 18 isomers are possible via amide formation and resulting through condensation of the 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-difluorobenzoyl chlorides with the 4-/3-/2-aminopyridines. The 2,3-, 2,4- and 2,5-difluoro-N-(4-pyridyl)benzamides have already been reported by us (McMahon et al., 2008). Systematic structural analyses have recently been reported for related fluoro derivatives (Chopra & Row, 2008) and isomeric series (Gelbrich et al., 2007).

There is a dearth of structural information in the literature on all six possible difluorobenzene derivatives F₂C₆H₃—Z (Z = remainder of molecule) from analysis of structural data in the Cambridge Structural Database (Allen 2002; v5.29, Nov 2007 issue + 2 updates). In this structural report the structure of 2,3-difluoro-N-(2-pyridyl)benzamide (I), Fig. 1, is described.

Compound (I) crystallizes with two molecules, A and B (which differ slightly in conformation) in the asymmetric unit: the C₆/C₅N internal angles are 51.58 (5)° and 49.97 (4)°, respectively, see overlay diagram, Fig. 2. Molecules aggregate via N—H···N interactions as hydrogen bonded dimers with structural motif R₂²(8); see Table 1 for geometric parameters. The [N1A/C21A/N22A/H1A] and [N1B/C21B/N22B/H1B] interplanar angle is 36.2 (3)° and deviates considerably from co-planarity therefore highlighting a degree of twist between the two interacting molecules. Hydrogen bonded dimers are linked into a supramolecular chain via C—H···O=C intermolecular interactions, Table 1 and Fig. 3.

An analysis of the Cambridge Structural Database reveals a related structure pentafluoro-N-(2-pyridyl)benzamide (II) [CSD code IDALAA] (Forbes et al., 2001) where molecules also form hydrogen bonded dimers in space group P1 (No. 2) with Z'=2. The N···N intermolecular distances in (II) are 2.9568 (14) and 3.0734 (15) Å.

Related literature top

For background information, see: Chopra & Row (2008); Donnelly et al. (2008); Gelbrich et al. (2007); McMahon et al. (2008). For a related structure, see: Forbes et al. (2001). For the Cambridge Structural Database, see: Allen (2002).

Experimental top

Compound (I) was synthesized via standard condensation procedures and similar to the related syntheses reported previously (Donnelly et al., 2008; McMahon et al., 2008).

Typical organic workup and washing gave the product (I) in modest yield of 15–20%. Crystals suitable for diffraction were grown from CHCl₃ solution as colourless blocks over a period of 1–2 weeks. The compounds gave clean ¹H and ¹³C NMR spectra in δ₆-DMSO and infrared spectra (in CHCl₃ solution, and as KBr disks).

For (I), m.p. 348–352 K (uncorrected). IR (ν_C=O cm^-1): 1644(s), (CHCl₃); 1695(s) (KBr). ¹H NMR (400 MHz, DMSO): δ 11.02 (s, 1H, N—H), 8.38 (d, 1H), 8.18 (d, 1H), 7.87 (t, 1H), 7.61 (q, 1H), 7.50 (t, 1H), 7.34 (q, 1H), 7.19 (t, 1H).

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: 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).

Figures top

	Fig. 1. A view of the hydrogen bonded dimeric unit in (I) with the atomic numbering scheme for the two independent molecules A and B. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. An overlay of the non-H atoms in molecules A and B in (I).
	Fig. 3. A view of the primary interactions in the crystal structure of (I) with H atoms not involved in hydrogen bonding removed for clarity. Molecules in the hydrogen bonded dimer with suffixes A and B are linked to symmetry related dimers at positions * and # via C—H···O interactions.

2,3-Difluoro-N-(2-pyridyl)benzamide top

Crystal data top

C₁₂H₈F₂N₂O	F(000) = 960
M_r = 234.20	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 350 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.8515 (4) Å	Cell parameters from 19375 reflections
b = 9.0554 (2) Å	θ = 2.6–27.5°
c = 20.1075 (7) Å	µ = 0.12 mm⁻¹
β = 100.2620 (15)°	T = 150 K
V = 2123.42 (11) Å³	Block, colorless
Z = 8	0.26 × 0.20 × 0.15 mm

Data collection top

Nonius KappaCCD diffractometer	4803 independent reflections
Radiation source: fine-focus sealed X-ray tube	3170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ, ω scans with κ offsets	θ_max = 27.4°, θ_min = 2.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −15→15
T_min = 0.875, T_max = 0.981	k = −11→11
5113 measured reflections	l = −25→26

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0702P)² + 0.0466P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4803 reflections	Δρ_max = 0.22 e Å⁻³
316 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0082 (18)

Crystal data top

C₁₂H₈F₂N₂O	V = 2123.42 (11) Å³
M_r = 234.20	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8515 (4) Å	µ = 0.12 mm⁻¹
b = 9.0554 (2) Å	T = 150 K
c = 20.1075 (7) Å	0.26 × 0.20 × 0.15 mm
β = 100.2620 (15)°

Data collection top

Nonius KappaCCD diffractometer	4803 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3170 reflections with I > 2σ(I)
T_min = 0.875, T_max = 0.981	R_int = 0.045
5113 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
4803 reflections	Δρ_min = −0.23 e Å⁻³
316 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F12A	0.56446 (8)	0.44877 (11)	0.07324 (5)	0.0425 (3)
F13A	0.78621 (9)	0.51655 (11)	0.10099 (5)	0.0488 (3)
O1A	0.42720 (10)	0.20016 (14)	−0.08253 (6)	0.0395 (3)
C1A	0.47361 (14)	0.22193 (17)	−0.02420 (8)	0.0305 (4)
N1A	0.42289 (12)	0.20469 (17)	0.03102 (7)	0.0335 (3)
C11A	0.59705 (14)	0.26753 (17)	−0.00730 (8)	0.0290 (4)
C12A	0.63682 (14)	0.37604 (18)	0.03976 (8)	0.0321 (4)
C13A	0.75099 (15)	0.41319 (18)	0.05327 (9)	0.0355 (4)
C14A	0.82865 (15)	0.3464 (2)	0.02003 (9)	0.0393 (4)
C15A	0.79011 (15)	0.2389 (2)	−0.02769 (9)	0.0381 (4)
C16A	0.67583 (15)	0.20015 (18)	−0.04120 (8)	0.0325 (4)
C21A	0.30662 (14)	0.18055 (17)	0.03269 (8)	0.0299 (4)
N22A	0.28635 (11)	0.16084 (15)	0.09545 (7)	0.0314 (3)
C23A	0.17744 (14)	0.13679 (18)	0.10248 (9)	0.0346 (4)
C24A	0.08688 (15)	0.13592 (19)	0.04919 (9)	0.0377 (4)
C25A	0.10971 (15)	0.1603 (2)	−0.01501 (10)	0.0410 (4)
C26A	0.22090 (15)	0.18089 (18)	−0.02435 (9)	0.0350 (4)
F12B	0.29582 (9)	0.49048 (12)	0.14007 (5)	0.0443 (3)
F13B	0.06988 (10)	0.53646 (13)	0.11073 (6)	0.0554 (3)
O1B	0.45792 (11)	0.38227 (17)	0.31766 (6)	0.0555 (4)
C1B	0.40611 (15)	0.34390 (19)	0.26233 (8)	0.0354 (4)
N1B	0.45292 (12)	0.27166 (16)	0.21504 (7)	0.0325 (3)
C11B	0.27918 (14)	0.37060 (18)	0.24278 (8)	0.0328 (4)
C12B	0.22995 (15)	0.44225 (18)	0.18387 (8)	0.0345 (4)
C13B	0.11332 (16)	0.46598 (19)	0.16891 (9)	0.0386 (4)
C14B	0.04218 (16)	0.4186 (2)	0.21145 (10)	0.0421 (4)
C15B	0.08962 (16)	0.3480 (2)	0.27087 (10)	0.0445 (5)
C16B	0.20703 (16)	0.3250 (2)	0.28624 (9)	0.0395 (4)
C21B	0.56780 (14)	0.22849 (17)	0.21788 (8)	0.0303 (4)
N22B	0.58589 (12)	0.16736 (16)	0.16024 (7)	0.0344 (3)
C23B	0.69244 (15)	0.1202 (2)	0.15795 (9)	0.0384 (4)
C24B	0.78295 (15)	0.1326 (2)	0.21110 (9)	0.0389 (4)
C25B	0.76225 (16)	0.1964 (2)	0.27011 (9)	0.0427 (5)
C26B	0.65348 (15)	0.2447 (2)	0.27418 (9)	0.0390 (4)
H1A	0.4709 (16)	0.1978 (19)	0.0706 (9)	0.035 (5)*
H14A	0.9074	0.3732	0.0295	0.047*
H15A	0.8428	0.1916	−0.0512	0.046*
H16A	0.6505	0.1264	−0.0741	0.039*
H23A	0.1621	0.1195	0.1466	0.042*
H24A	0.0108	0.1191	0.0563	0.045*
H25A	0.0486	0.1628	−0.0527	0.049*
H26A	0.2384	0.1949	−0.0682	0.042*
H1B	0.4059 (17)	0.240 (2)	0.1778 (10)	0.043 (5)*
H14B	−0.0383	0.4340	0.2003	0.051*
H15B	0.0418	0.3153	0.3011	0.053*
H16B	0.2388	0.2770	0.3273	0.047*
H23B	0.7063	0.0758	0.1174	0.046*
H24B	0.8573	0.0983	0.2073	0.047*
H25B	0.8227	0.2069	0.3077	0.051*
H26B	0.6375	0.2881	0.3145	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F12A	0.0384 (6)	0.0438 (6)	0.0455 (6)	0.0052 (4)	0.0084 (5)	−0.0136 (5)
F13A	0.0455 (7)	0.0452 (6)	0.0519 (7)	−0.0065 (5)	−0.0018 (5)	−0.0134 (5)
O1A	0.0386 (7)	0.0519 (8)	0.0264 (7)	−0.0028 (5)	0.0015 (5)	−0.0038 (5)
C1A	0.0317 (9)	0.0328 (9)	0.0258 (9)	0.0030 (7)	0.0020 (7)	−0.0014 (7)
N1A	0.0241 (8)	0.0508 (9)	0.0244 (8)	−0.0028 (6)	0.0008 (6)	−0.0018 (6)
C11A	0.0311 (9)	0.0313 (8)	0.0243 (8)	0.0017 (6)	0.0040 (7)	0.0021 (7)
C12A	0.0321 (9)	0.0333 (9)	0.0315 (9)	0.0058 (7)	0.0073 (7)	−0.0006 (7)
C13A	0.0371 (10)	0.0326 (9)	0.0342 (9)	−0.0036 (7)	−0.0008 (8)	−0.0017 (8)
C14A	0.0286 (9)	0.0461 (10)	0.0428 (11)	−0.0013 (8)	0.0055 (8)	0.0042 (9)
C15A	0.0334 (10)	0.0468 (10)	0.0352 (10)	0.0067 (8)	0.0093 (8)	0.0025 (8)
C16A	0.0373 (10)	0.0337 (9)	0.0266 (9)	0.0030 (7)	0.0056 (7)	0.0006 (7)
C21A	0.0286 (9)	0.0308 (8)	0.0296 (9)	0.0011 (6)	0.0035 (7)	−0.0006 (7)
N22A	0.0286 (8)	0.0353 (8)	0.0300 (8)	−0.0001 (6)	0.0047 (6)	−0.0010 (6)
C23A	0.0357 (10)	0.0339 (9)	0.0354 (10)	−0.0019 (7)	0.0095 (8)	−0.0022 (7)
C24A	0.0296 (9)	0.0401 (10)	0.0426 (11)	−0.0049 (7)	0.0041 (8)	−0.0015 (8)
C25A	0.0322 (10)	0.0476 (11)	0.0389 (10)	−0.0033 (8)	−0.0048 (8)	−0.0009 (8)
C26A	0.0320 (10)	0.0417 (10)	0.0292 (9)	−0.0011 (7)	−0.0003 (7)	0.0016 (8)
F12B	0.0424 (6)	0.0497 (6)	0.0426 (6)	0.0017 (5)	0.0121 (5)	0.0126 (5)
F13B	0.0462 (7)	0.0643 (7)	0.0531 (7)	0.0097 (5)	0.0014 (5)	0.0206 (6)
O1B	0.0459 (8)	0.0824 (10)	0.0345 (8)	0.0130 (7)	−0.0024 (6)	−0.0221 (7)
C1B	0.0376 (10)	0.0408 (10)	0.0272 (9)	0.0025 (7)	0.0041 (8)	−0.0026 (8)
N1B	0.0296 (8)	0.0422 (8)	0.0243 (7)	0.0018 (6)	0.0008 (6)	−0.0035 (6)
C11B	0.0360 (10)	0.0340 (9)	0.0286 (9)	0.0021 (7)	0.0060 (7)	−0.0057 (7)
C12B	0.0374 (10)	0.0356 (9)	0.0320 (9)	−0.0011 (7)	0.0103 (8)	−0.0003 (8)
C13B	0.0389 (11)	0.0376 (10)	0.0377 (10)	0.0043 (8)	0.0022 (8)	0.0030 (8)
C14B	0.0336 (10)	0.0465 (10)	0.0459 (11)	0.0018 (8)	0.0063 (8)	−0.0054 (9)
C15B	0.0417 (11)	0.0544 (11)	0.0402 (11)	−0.0027 (9)	0.0148 (9)	−0.0056 (9)
C16B	0.0420 (11)	0.0489 (11)	0.0284 (9)	0.0032 (8)	0.0084 (8)	−0.0017 (8)
C21B	0.0330 (9)	0.0310 (8)	0.0266 (9)	0.0001 (6)	0.0043 (7)	0.0011 (7)
N22B	0.0331 (8)	0.0393 (8)	0.0292 (8)	0.0037 (6)	0.0015 (6)	−0.0024 (6)
C23B	0.0364 (10)	0.0424 (10)	0.0355 (10)	0.0076 (8)	0.0045 (8)	−0.0038 (8)
C24B	0.0303 (10)	0.0458 (10)	0.0387 (10)	0.0035 (7)	0.0014 (8)	0.0024 (8)
C25B	0.0350 (10)	0.0552 (12)	0.0342 (10)	−0.0007 (8)	−0.0037 (8)	−0.0006 (9)
C26B	0.0367 (10)	0.0504 (11)	0.0280 (9)	0.0002 (8)	0.0006 (8)	−0.0023 (8)

Geometric parameters (Å, º) top

F12A—C12A	1.3520 (18)	C12B—C13B	1.378 (2)
F13A—C13A	1.3522 (19)	C13B—C14B	1.373 (3)
O1A—C1A	1.2195 (19)	C14B—C15B	1.383 (3)
C1A—N1A	1.363 (2)	C15B—C16B	1.386 (3)
C1A—C11A	1.500 (2)	C21B—N22B	1.336 (2)
N1A—C21A	1.402 (2)	C21B—C26B	1.387 (2)
C11A—C12A	1.387 (2)	N22B—C23B	1.342 (2)
C11A—C16A	1.391 (2)	C23B—C24B	1.377 (2)
C12A—C13A	1.374 (2)	C24B—C25B	1.380 (3)
C13A—C14A	1.371 (2)	C25B—C26B	1.377 (3)
C14A—C15A	1.386 (3)	N1A—H1A	0.894 (19)
C15A—C16A	1.378 (2)	C14A—H14A	0.9500
C21A—N22A	1.338 (2)	C15A—H15A	0.9500
C21A—C26A	1.390 (2)	C16A—H16A	0.9500
N22A—C23A	1.341 (2)	C23A—H23A	0.9500
C23A—C24A	1.375 (2)	C24A—H24A	0.9500
C24A—C25A	1.383 (3)	C25A—H25A	0.9500
C25A—C26A	1.377 (2)	C26A—H26A	0.9500
F12B—C12B	1.3493 (19)	N1B—H1B	0.90 (2)
F13B—C13B	1.351 (2)	C14B—H14B	0.9500
O1B—C1B	1.221 (2)	C15B—H15B	0.9500
C1B—N1B	1.352 (2)	C16B—H16B	0.9500
C1B—C11B	1.505 (2)	C23B—H23B	0.9500
N1B—C21B	1.408 (2)	C24B—H24B	0.9500
C11B—C12B	1.385 (2)	C25B—H25B	0.9500
C11B—C16B	1.390 (2)	C26B—H26B	0.9500

O1A—C1A—N1A	125.19 (16)	O1B—C1B—N1B	125.13 (16)
O1A—C1A—C11A	121.14 (15)	O1B—C1B—C11B	120.60 (15)
N1A—C1A—C11A	113.64 (14)	N1B—C1B—C11B	114.22 (14)
C1A—N1A—C21A	128.01 (14)	C1B—N1B—C21B	128.38 (14)
C1A—N1A—H1A	115.5 (11)	C1B—N1B—H1B	118.2 (12)
C21A—N1A—H1A	116.1 (11)	C21B—N1B—H1B	113.3 (12)
C12A—C11A—C16A	117.95 (15)	C12B—C11B—C16B	117.68 (16)
C12A—C11A—C1A	123.29 (15)	C12B—C11B—C1B	123.21 (15)
C16A—C11A—C1A	118.75 (15)	C16B—C11B—C1B	119.09 (15)
F12A—C12A—C11A	121.07 (15)	F12B—C12B—C11B	120.36 (15)
F12A—C12A—C13A	118.17 (15)	F12B—C12B—C13B	118.78 (15)
C13A—C12A—C11A	120.76 (15)	C13B—C12B—C11B	120.86 (16)
F13A—C13A—C12A	118.59 (15)	F13B—C13B—C12B	118.38 (16)
F13A—C13A—C14A	120.15 (16)	F13B—C13B—C14B	120.37 (17)
C14A—C13A—C12A	121.25 (16)	C14B—C13B—C12B	121.25 (17)
C13A—C14A—C15A	118.72 (17)	C13B—C14B—C15B	118.86 (17)
C16A—C15A—C14A	120.42 (16)	C14B—C15B—C16B	119.97 (17)
C15A—C16A—C11A	120.89 (16)	C15B—C16B—C11B	121.37 (17)
N22A—C21A—C26A	123.43 (15)	N22B—C21B—C26B	123.00 (16)
N22A—C21A—N1A	112.70 (14)	N22B—C21B—N1B	112.55 (14)
C26A—C21A—N1A	123.84 (15)	C26B—C21B—N1B	124.44 (15)
C21A—N22A—C23A	117.32 (14)	C21B—N22B—C23B	117.33 (14)
N22A—C23A—C24A	123.44 (16)	N22B—C23B—C24B	123.73 (17)
C23A—C24A—C25A	118.11 (16)	C23B—C24B—C25B	117.90 (17)
C26A—C25A—C24A	120.02 (16)	C26B—C25B—C24B	119.71 (17)
C25A—C26A—C21A	117.62 (16)	C25B—C26B—C21B	118.32 (16)
C13A—C14A—H14A	120.6	C13B—C14B—H14B	120.6
C15A—C14A—H14A	120.6	C15B—C14B—H14B	120.6
C16A—C15A—H15A	119.8	C14B—C15B—H15B	120.0
C14A—C15A—H15A	119.8	C16B—C15B—H15B	120.0
C15A—C16A—H16A	119.6	C15B—C16B—H16B	119.3
C11A—C16A—H16A	119.6	C11B—C16B—H16B	119.3
C23A—C24A—H24A	120.9	N22B—C23B—H23B	118.1
C25A—C24A—H24A	120.9	C24B—C23B—H23B	118.1
C26A—C25A—H25A	120.0	C23B—C24B—H24B	121.0
C24A—C25A—H25A	120.0	C25B—C24B—H24B	121.0
N22A—C23A—H23A	118.3	C26B—C25B—H25B	120.1
C24A—C23A—H23A	118.3	C24B—C25B—H25B	120.1
C25A—C26A—H26A	121.2	C25B—C26B—H26B	120.8
C21A—C26A—H26A	121.2	C21B—C26B—H26B	120.8

O1A—C1A—N1A—C21A	−10.0 (3)	O1B—C1B—N1B—C21B	−1.4 (3)
C11A—C1A—N1A—C21A	171.67 (15)	C11B—C1B—N1B—C21B	−179.18 (15)
O1A—C1A—C11A—C12A	137.44 (17)	O1B—C1B—C11B—C12B	127.03 (19)
N1A—C1A—C11A—C12A	−44.2 (2)	N1B—C1B—C11B—C12B	−55.1 (2)
O1A—C1A—C11A—C16A	−41.3 (2)	O1B—C1B—C11B—C16B	−51.4 (2)
N1A—C1A—C11A—C16A	137.08 (16)	N1B—C1B—C11B—C16B	126.52 (17)
C16A—C11A—C12A—F12A	178.24 (14)	C16B—C11B—C12B—F12B	179.31 (15)
C1A—C11A—C12A—F12A	−0.5 (2)	C1B—C11B—C12B—F12B	0.9 (2)
C16A—C11A—C12A—C13A	−1.3 (2)	C16B—C11B—C12B—C13B	−0.5 (2)
C1A—C11A—C12A—C13A	179.93 (16)	C1B—C11B—C12B—C13B	−178.94 (16)
F12A—C12A—C13A—F13A	2.4 (2)	F12B—C12B—C13B—F13B	0.2 (2)
C11A—C12A—C13A—F13A	−178.07 (15)	C11B—C12B—C13B—F13B	180.00 (15)
F12A—C12A—C13A—C14A	−178.45 (15)	F12B—C12B—C13B—C14B	179.65 (16)
C11A—C12A—C13A—C14A	1.1 (3)	C11B—C12B—C13B—C14B	−0.5 (3)
F13A—C13A—C14A—C15A	178.79 (16)	F13B—C13B—C14B—C15B	−179.45 (16)
C12A—C13A—C14A—C15A	−0.4 (3)	C12B—C13B—C14B—C15B	1.1 (3)
C13A—C14A—C15A—C16A	−0.1 (3)	C13B—C14B—C15B—C16B	−0.6 (3)
C14A—C15A—C16A—C11A	−0.1 (3)	C14B—C15B—C16B—C11B	−0.5 (3)
C12A—C11A—C16A—C15A	0.8 (2)	C12B—C11B—C16B—C15B	1.0 (3)
C1A—C11A—C16A—C15A	179.64 (15)	C1B—C11B—C16B—C15B	179.48 (16)
C1A—N1A—C21A—N22A	176.76 (16)	C1B—N1B—C21B—N22B	−175.88 (16)
C1A—N1A—C21A—C26A	−4.9 (3)	C1B—N1B—C21B—C26B	5.0 (3)
C26A—C21A—N22A—C23A	1.7 (2)	C26B—C21B—N22B—C23B	0.1 (2)
N1A—C21A—N22A—C23A	−179.97 (14)	N1B—C21B—N22B—C23B	−179.03 (15)
C21A—N22A—C23A—C24A	−2.0 (2)	C21B—N22B—C23B—C24B	−0.5 (3)
N22A—C23A—C24A—C25A	0.4 (3)	N22B—C23B—C24B—C25B	0.4 (3)
C23A—C24A—C25A—C26A	1.6 (3)	C23B—C24B—C25B—C26B	0.2 (3)
C24A—C25A—C26A—C21A	−1.9 (3)	C24B—C25B—C26B—C21B	−0.6 (3)
N22A—C21A—C26A—C25A	0.2 (3)	N22B—C21B—C26B—C25B	0.5 (3)
N1A—C21A—C26A—C25A	−177.96 (16)	N1B—C21B—C26B—C25B	179.45 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N22B	0.894 (19)	2.076 (19)	2.968 (2)	175.9 (16)
N1B—H1B···N22A	0.90 (2)	2.10 (2)	2.999 (2)	175.4 (17)
C26A—H26A···O1A	0.95	2.31	2.898 (2)	120
C26B—H26B···O1B	0.95	2.30	2.900 (2)	120
C25B—H25B···O1Aⁱ	0.95	2.48	3.379 (2)	159
C25A—H25A···O1Bⁱⁱ	0.95	2.67	3.542 (2)	153

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₈F₂N₂O
M_r	234.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	11.8515 (4), 9.0554 (2), 20.1075 (7)
β (°)	100.2620 (15)
V (Å³)	2123.42 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.26 × 0.20 × 0.15

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.875, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	5113, 4803, 3170
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.128, 1.04
No. of reflections	4803
No. of parameters	316
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

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).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N22B	0.894 (19)	2.076 (19)	2.968 (2)	175.9 (16)
N1B—H1B···N22A	0.90 (2)	2.10 (2)	2.999 (2)	175.4 (17)
C25B—H25B···O1Aⁱ	0.95	2.48	3.379 (2)	159
C25A—H25A···O1Bⁱⁱ	0.95	2.67	3.542 (2)	153

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: alough@chem.utoronto.ca.

Acknowledgements

JFG thanks Dublin City University for the grants in aid of undergraduate research. Thanks especially to Mr Damien McGuirk for providing excellent technical assistance in the undergraduate research laboratories.

References

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