3,6-Dichloro-N-(4-fluoro-phen-yl)picolinamide.

In the title compound, C(12)H(7)Cl(2)FN(2)O, the dihedral angle between the phenyl and pyridine rings is 42.5 (2) Å and an intramolecular N-H⋯N hydrogen bond occurs. The crystal structure is stabilized by C-H⋯O, C-H⋯F and C-Cl short contacts.

Related literature

For the chemical and pharmacological properties of amides, see: Liu et al. (2005 ▶); Sladowska & Sieklucka-Dziuba (1999 ▶).

Experimental

Crystal data

C12H7Cl2FN2O

M = 285.10

Orthorhombic,

a = 24.921 (2) Å

b = 4.3735 (6) Å

c = 11.1723 (14) Å

V = 1217.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 298 K

0.45 × 0.33 × 0.31 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.796, T max = 0.852

5652 measured reflections

1959 independent reflections

1582 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 1.08

1959 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 826 Friedel pairs

Flack parameter: −0.04 (12)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024799/hg2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024799/hg2522Isup2.hkl

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

C12H7Cl2FN2O	F(000) = 576
Mr = 285.10	Dx = 1.555 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1638 reflections
a = 24.921 (2) Å	θ = 2.9–27.0°
b = 4.3735 (6) Å	µ = 0.53 mm−1
c = 11.1723 (14) Å	T = 298 K
V = 1217.7 (2) Å3	Block, colorless
Z = 4	0.45 × 0.33 × 0.31 mm

Bruker SMART CCD diffractometer	1959 independent reflections
Radiation source: fine-focus sealed tube	1582 reflections with I > 2σ(I)
graphite	Rint = 0.066
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→26
Tmin = 0.796, Tmax = 0.852	k = −5→5
5652 measured reflections	l = −13→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.2751P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.140	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.21 e Å−3
1959 reflections	Δρmin = −0.20 e Å−3
163 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
1 restraint	Extinction coefficient: 0.064 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 826 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.04 (12)

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
Cl1	0.29548 (4)	0.3691 (3)	0.97142 (12)	0.0657 (4)
Cl2	0.10409 (7)	0.8942 (4)	0.69084 (13)	0.0830 (5)
N1	0.14698 (14)	0.5722 (9)	0.8609 (3)	0.0479 (9)
N2	0.11700 (14)	0.2081 (9)	1.0330 (3)	0.0468 (9)
H2	0.0985	0.2817	0.9747	0.056*
F1	−0.00073 (16)	−0.4220 (10)	1.3695 (4)	0.1088 (14)
O1	0.20091 (13)	0.1700 (12)	1.1055 (4)	0.0917 (17)
C1	0.17010 (17)	0.2639 (11)	1.0316 (4)	0.0491 (11)
C2	0.18767 (17)	0.4557 (11)	0.9264 (4)	0.0449 (11)
C3	0.24053 (16)	0.5164 (10)	0.8958 (4)	0.0430 (10)
C4	0.2520 (2)	0.7023 (11)	0.7983 (4)	0.0523 (11)
H4	0.2873	0.7439	0.7771	0.063*
C5	0.2098 (2)	0.8244 (12)	0.7333 (5)	0.0566 (12)
H5	0.2157	0.9518	0.6680	0.068*
C6	0.15852 (18)	0.7482 (11)	0.7701 (4)	0.0493 (11)
C7	0.08862 (17)	0.0410 (10)	1.1205 (4)	0.0418 (10)
C8	0.1042 (2)	0.0484 (13)	1.2409 (5)	0.0595 (13)
H8	0.1342	0.1585	1.2654	0.071*
C9	0.0732 (2)	−0.1150 (15)	1.3226 (5)	0.0756 (17)
H9	0.0829	−0.1168	1.4030	0.091*
C10	0.0290 (2)	−0.2722 (14)	1.2864 (6)	0.0714 (16)
C11	0.0144 (2)	−0.2826 (13)	1.1691 (6)	0.0688 (15)
H11	−0.0155	−0.3947	1.1457	0.083*
C12	0.04429 (18)	−0.1262 (13)	1.0851 (5)	0.0559 (13)
H12	0.0346	−0.1332	1.0048	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.0458 (6)	0.0924 (10)	0.0588 (7)	0.0066 (6)	0.0025 (6)	0.0119 (8)
Cl2	0.0762 (9)	0.0970 (11)	0.0756 (10)	−0.0019 (8)	−0.0244 (8)	0.0324 (9)
N1	0.052 (2)	0.050 (2)	0.042 (2)	−0.0034 (18)	0.0024 (18)	0.0056 (19)
N2	0.0447 (19)	0.055 (2)	0.040 (2)	−0.0029 (17)	−0.0053 (16)	0.0082 (18)
F1	0.110 (3)	0.108 (3)	0.108 (3)	−0.014 (2)	0.051 (2)	0.036 (2)
O1	0.048 (2)	0.148 (5)	0.079 (3)	0.003 (2)	−0.0076 (18)	0.068 (3)
C1	0.044 (2)	0.055 (3)	0.048 (3)	0.003 (2)	0.000 (2)	0.007 (2)
C2	0.047 (2)	0.055 (3)	0.032 (2)	0.005 (2)	0.0023 (18)	0.000 (2)
C3	0.049 (2)	0.043 (2)	0.037 (2)	−0.0003 (19)	0.0002 (19)	−0.0018 (18)
C4	0.056 (3)	0.058 (3)	0.043 (3)	−0.007 (2)	0.009 (2)	0.001 (2)
C5	0.071 (3)	0.057 (3)	0.042 (3)	−0.008 (2)	0.001 (2)	0.011 (2)
C6	0.054 (3)	0.052 (3)	0.042 (3)	−0.003 (2)	−0.006 (2)	0.001 (2)
C7	0.047 (2)	0.037 (2)	0.042 (3)	0.0010 (19)	0.009 (2)	0.0005 (19)
C8	0.054 (3)	0.073 (4)	0.052 (3)	−0.004 (3)	0.003 (2)	0.005 (3)
C9	0.082 (4)	0.096 (5)	0.049 (3)	0.008 (3)	0.017 (3)	0.018 (3)
C10	0.072 (4)	0.065 (4)	0.078 (4)	0.004 (3)	0.034 (3)	0.017 (3)
C11	0.053 (3)	0.062 (3)	0.092 (5)	−0.010 (2)	0.017 (3)	−0.001 (3)
C12	0.049 (3)	0.062 (3)	0.057 (3)	−0.007 (2)	0.003 (2)	−0.002 (2)

Cl1—C3	1.734 (4)	C4—H4	0.9300
Cl2—C6	1.741 (5)	C5—C6	1.383 (6)
N1—C6	1.305 (6)	C5—H5	0.9300
N1—C2	1.351 (6)	C7—C12	1.383 (7)
N2—C1	1.346 (5)	C7—C8	1.400 (7)
N2—C7	1.411 (6)	C8—C9	1.393 (7)
N2—H2	0.8600	C8—H8	0.9300
F1—C10	1.356 (6)	C9—C10	1.361 (9)
O1—C1	1.200 (5)	C9—H9	0.9300
C1—C2	1.508 (6)	C10—C11	1.360 (9)
C2—C3	1.387 (6)	C11—C12	1.379 (8)
C3—C4	1.389 (6)	C11—H11	0.9300
C4—C5	1.385 (7)	C12—H12	0.9300
C6—N1—C2	118.6 (4)	N1—C6—Cl2	116.1 (3)
C1—N2—C7	126.5 (4)	C5—C6—Cl2	118.7 (4)
C1—N2—H2	116.7	C12—C7—C8	120.6 (4)
C7—N2—H2	116.7	C12—C7—N2	118.4 (4)
O1—C1—N2	124.0 (4)	C8—C7—N2	120.9 (4)
O1—C1—C2	122.7 (4)	C9—C8—C7	117.6 (5)
N2—C1—C2	113.3 (4)	C9—C8—H8	121.2
N1—C2—C3	120.5 (4)	C7—C8—H8	121.2
N1—C2—C1	114.5 (4)	C10—C9—C8	120.9 (5)
C3—C2—C1	125.1 (4)	C10—C9—H9	119.5
C2—C3—C4	120.1 (4)	C8—C9—H9	119.5
C2—C3—Cl1	124.0 (3)	F1—C10—C11	119.9 (6)
C4—C3—Cl1	115.9 (3)	F1—C10—C9	118.9 (6)
C5—C4—C3	118.7 (4)	C11—C10—C9	121.3 (5)
C5—C4—H4	120.6	C10—C11—C12	119.7 (5)
C3—C4—H4	120.6	C10—C11—H11	120.2
C6—C5—C4	116.9 (5)	C12—C11—H11	120.2
C6—C5—H5	121.6	C11—C12—C7	119.9 (5)
C4—C5—H5	121.6	C11—C12—H12	120.0
N1—C6—C5	125.2 (5)	C7—C12—H12	120.0
C7—N2—C1—O1	1.7 (8)	C2—N1—C6—Cl2	−179.2 (3)
C7—N2—C1—C2	−178.8 (4)	C4—C5—C6—N1	0.2 (8)
C6—N1—C2—C3	−1.6 (7)	C4—C5—C6—Cl2	−179.6 (4)
C6—N1—C2—C1	178.1 (4)	C1—N2—C7—C12	−147.3 (5)
O1—C1—C2—N1	−172.2 (5)	C1—N2—C7—C8	33.9 (7)
N2—C1—C2—N1	8.3 (6)	C12—C7—C8—C9	−0.7 (8)
O1—C1—C2—C3	7.5 (8)	N2—C7—C8—C9	178.1 (5)
N2—C1—C2—C3	−172.0 (4)	C7—C8—C9—C10	−0.9 (9)
N1—C2—C3—C4	1.1 (7)	C8—C9—C10—F1	−178.5 (5)
C1—C2—C3—C4	−178.5 (4)	C8—C9—C10—C11	2.0 (10)
N1—C2—C3—Cl1	−178.1 (3)	F1—C10—C11—C12	179.1 (5)
C1—C2—C3—Cl1	2.3 (7)	C9—C10—C11—C12	−1.4 (9)
C2—C3—C4—C5	0.1 (7)	C10—C11—C12—C7	−0.2 (8)
Cl1—C3—C4—C5	179.3 (4)	C8—C7—C12—C11	1.3 (8)
C3—C4—C5—C6	−0.7 (7)	N2—C7—C12—C11	−177.5 (4)
C2—N1—C6—C5	0.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1	0.86	2.17	2.606 (5)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1	0.86	2.17	2.606 (5)	111