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

The title compound, C(12)H(8)F(2)N(2)O, crystallizes with two independent mol-ecules in the asymmetric unit. The independent mol-ecules 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, mol-ecules aggregate via N-H⋯N(pyridine) inter-actions as hydrogen-bonded dimers with the structural motif R(2) (2)(8), and these dimers are linked via C-H⋯O inter-actions to form a supra-molecular 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 = 234.20

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.128

S = 1.04

4803 reflections

316 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.23 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/S1600536808038269/tk2329sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H8F2N2O	F000 = 960
Mr = 234.20	Dx = 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 = 2.6–27.5º
c = 20.1075 (7) Å	µ = 0.12 mm−1
β = 100.2620 (15)º	T = 150 (1) K
V = 2123.42 (11) Å3	Block, colorless
Z = 8	0.26 × 0.20 × 0.15 mm

Nonius KappaCCD diffractometer	4803 independent reflections
Radiation source: fine-focus sealed X-ray tube	3170 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
T = 150(1) K	θmax = 27.4º
φ, ω scans with κ offsets	θmin = 2.9º
Absorption correction: multi-scan(SORTAV; Blessing, 1995)	h = −15→15
Tmin = 0.875, Tmax = 0.981	k = −11→11
5113 measured reflections	l = −25→26

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.0466P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.128	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.22 e Å−3
4803 reflections	Δρmin = −0.23 e Å−3
316 parameters	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)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .