3,6-Dichloro-N-(4,6-dichloro-pyrimidin-2-yl)picolinamide.

In the title compound, C(10)H(4)Cl(4)N(4)O, the pyridine and pyrimidine rings are nearly perpendicular to each other, the dihedral angle between them being 86.60 (10)°. In the crystal structure, the N and O atoms in the amide group are involved in inter-molecular hydrogen bonds, forming a one-dimensional chain along the c axis.

Related literature

For related literature, see: Liu et al. (2005 ▶); Śladowska et al. (1999 ▶).

Experimental

Crystal data

C10H4Cl4N4O

M = 337.97

Monoclinic,

a = 10.9313 (13) Å

b = 13.3682 (14) Å

c = 9.3846 (10) Å

β = 112.576 (1)°

V = 1266.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.93 mm−1

T = 293 (2) K

0.48 × 0.43 × 0.40 mm

Data collection

Bruker SMART 1000 diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.648, T max = 0.690

15165 measured reflections

2494 independent reflections

2132 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.02

2494 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.30 e Å−3

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/S1600536808010325/is2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010325/is2279Isup2.hkl

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

C10H4Cl4N4O	F000 = 672
Mr = 337.97	Dx = 1.773 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5203 reflections
a = 10.9313 (13) Å	θ = 2.5–27.9º
b = 13.3682 (14) Å	µ = 0.93 mm−1
c = 9.3846 (10) Å	T = 293 (2) K
β = 112.576 (1)º	Block, colorless
V = 1266.3 (2) Å3	0.48 × 0.43 × 0.40 mm
Z = 4

Bruker SMART 1000 diffractometer	2494 independent reflections
Radiation source: fine-focus sealed tube	2132 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
T = 293(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.648, Tmax = 0.690	k = −14→16
15165 measured reflections	l = −11→11

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.054P)2 + 0.512P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2494 reflections	Δρmax = 0.34 e Å−3
172 parameters	Δρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.35795 (6)	0.27703 (5)	−0.13818 (7)	0.05603 (19)
Cl2	0.62475 (7)	0.54097 (5)	0.43365 (8)	0.0654 (2)
Cl3	1.09988 (5)	0.21157 (5)	−0.02538 (7)	0.05207 (18)
Cl4	1.02903 (6)	−0.06103 (4)	0.35461 (7)	0.05590 (19)
N1	0.74081 (16)	0.23149 (13)	0.16663 (19)	0.0373 (4)
H1	0.7257	0.2261	0.2497	0.045*
N2	0.62326 (16)	0.40893 (13)	0.23044 (19)	0.0391 (4)
N3	0.87749 (16)	0.09425 (12)	0.24523 (19)	0.0365 (4)
N4	0.90814 (16)	0.21391 (12)	0.07244 (19)	0.0345 (4)
O1	0.65761 (15)	0.30109 (12)	−0.07433 (17)	0.0477 (4)
C1	0.65957 (19)	0.29263 (15)	0.0547 (2)	0.0343 (4)
C2	0.56552 (19)	0.35255 (15)	0.1045 (2)	0.0337 (4)
C3	0.4300 (2)	0.35264 (16)	0.0218 (2)	0.0377 (4)
C4	0.3507 (2)	0.41321 (17)	0.0706 (3)	0.0454 (5)
H4	0.2592	0.4137	0.0178	0.054*
C5	0.4096 (2)	0.47242 (16)	0.1984 (3)	0.0453 (5)
H5	0.3596	0.5148	0.2335	0.054*
C6	0.5450 (2)	0.46693 (16)	0.2728 (2)	0.0409 (5)
C7	0.84622 (18)	0.17692 (14)	0.1588 (2)	0.0326 (4)
C8	1.01267 (19)	0.16221 (16)	0.0782 (2)	0.0356 (4)
C9	1.0576 (2)	0.07605 (16)	0.1624 (2)	0.0410 (5)
H9	1.1317	0.0412	0.1640	0.049*
C10	0.9829 (2)	0.04607 (15)	0.2440 (2)	0.0372 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0484 (3)	0.0739 (4)	0.0436 (3)	−0.0043 (3)	0.0151 (3)	−0.0118 (3)
Cl2	0.0771 (4)	0.0715 (4)	0.0639 (4)	−0.0244 (3)	0.0452 (4)	−0.0292 (3)
Cl3	0.0420 (3)	0.0729 (4)	0.0502 (3)	0.0091 (2)	0.0275 (3)	0.0117 (3)
Cl4	0.0705 (4)	0.0384 (3)	0.0589 (4)	0.0150 (3)	0.0248 (3)	0.0111 (2)
N1	0.0406 (9)	0.0437 (10)	0.0356 (9)	0.0093 (7)	0.0234 (8)	0.0071 (7)
N2	0.0414 (9)	0.0450 (10)	0.0380 (9)	−0.0001 (8)	0.0231 (8)	−0.0001 (8)
N3	0.0422 (9)	0.0331 (9)	0.0357 (9)	0.0000 (7)	0.0166 (7)	0.0004 (7)
N4	0.0349 (8)	0.0366 (9)	0.0352 (9)	0.0011 (7)	0.0170 (7)	−0.0012 (7)
O1	0.0500 (9)	0.0659 (10)	0.0353 (8)	0.0160 (7)	0.0253 (7)	0.0077 (7)
C1	0.0358 (10)	0.0388 (11)	0.0343 (10)	0.0023 (8)	0.0200 (8)	0.0010 (8)
C2	0.0375 (10)	0.0354 (10)	0.0331 (10)	0.0065 (8)	0.0189 (8)	0.0065 (8)
C3	0.0408 (10)	0.0422 (11)	0.0321 (10)	0.0047 (9)	0.0162 (9)	0.0052 (8)
C4	0.0371 (11)	0.0534 (13)	0.0467 (12)	0.0141 (9)	0.0173 (9)	0.0106 (10)
C5	0.0550 (13)	0.0412 (12)	0.0508 (13)	0.0137 (10)	0.0327 (11)	0.0063 (10)
C6	0.0515 (12)	0.0377 (11)	0.0434 (11)	−0.0025 (9)	0.0292 (10)	0.0000 (9)
C7	0.0335 (9)	0.0336 (10)	0.0319 (9)	0.0006 (8)	0.0139 (8)	−0.0026 (8)
C8	0.0329 (9)	0.0437 (11)	0.0310 (9)	−0.0007 (8)	0.0132 (8)	−0.0039 (8)
C9	0.0372 (11)	0.0425 (12)	0.0431 (11)	0.0085 (9)	0.0153 (9)	−0.0033 (9)
C10	0.0421 (11)	0.0321 (10)	0.0331 (10)	0.0042 (8)	0.0098 (9)	−0.0023 (8)

Cl1—C3	1.729 (2)	N4—C7	1.335 (2)
Cl2—C6	1.734 (2)	O1—C1	1.208 (2)
Cl3—C8	1.732 (2)	C1—C2	1.512 (3)
Cl4—C10	1.726 (2)	C2—C3	1.383 (3)
N1—C1	1.358 (3)	C3—C4	1.387 (3)
N1—C7	1.389 (2)	C4—C5	1.373 (3)
N1—H1	0.8600	C4—H4	0.9300
N2—C6	1.323 (3)	C5—C6	1.375 (3)
N2—C2	1.338 (3)	C5—H5	0.9300
N3—C10	1.324 (3)	C8—C9	1.376 (3)
N3—C7	1.335 (3)	C9—C10	1.376 (3)
N4—C8	1.319 (3)	C9—H9	0.9300
C1—N1—C7	125.77 (15)	C4—C5—C6	117.70 (19)
C1—N1—H1	117.1	C4—C5—H5	121.1
C7—N1—H1	117.1	C6—C5—H5	121.1
C6—N2—C2	117.08 (17)	N2—C6—C5	124.9 (2)
C10—N3—C7	114.73 (16)	N2—C6—Cl2	115.41 (16)
C8—N4—C7	114.49 (17)	C5—C6—Cl2	119.64 (16)
O1—C1—N1	125.91 (17)	N4—C7—N3	127.17 (17)
O1—C1—C2	120.51 (18)	N4—C7—N1	117.50 (17)
N1—C1—C2	113.57 (15)	N3—C7—N1	115.27 (16)
N2—C2—C3	122.36 (17)	N4—C8—C9	125.06 (18)
N2—C2—C1	115.17 (17)	N4—C8—Cl3	115.62 (15)
C3—C2—C1	122.40 (18)	C9—C8—Cl3	119.29 (15)
C2—C3—C4	119.07 (19)	C10—C9—C8	113.97 (18)
C2—C3—Cl1	121.29 (15)	C10—C9—H9	123.0
C4—C3—Cl1	119.62 (17)	C8—C9—H9	123.0
C5—C4—C3	118.8 (2)	N3—C10—C9	124.56 (19)
C5—C4—H4	120.6	N3—C10—Cl4	116.92 (16)
C3—C4—H4	120.6	C9—C10—Cl4	118.52 (16)
C7—N1—C1—O1	8.1 (3)	C4—C5—C6—N2	0.1 (3)
C7—N1—C1—C2	−172.25 (18)	C4—C5—C6—Cl2	179.38 (17)
C6—N2—C2—C3	−1.0 (3)	C8—N4—C7—N3	−1.4 (3)
C6—N2—C2—C1	176.22 (17)	C8—N4—C7—N1	175.62 (17)
O1—C1—C2—N2	−124.1 (2)	C10—N3—C7—N4	0.9 (3)
N1—C1—C2—N2	56.2 (2)	C10—N3—C7—N1	−176.17 (17)
O1—C1—C2—C3	53.0 (3)	C1—N1—C7—N4	29.0 (3)
N1—C1—C2—C3	−126.6 (2)	C1—N1—C7—N3	−153.63 (19)
N2—C2—C3—C4	0.0 (3)	C7—N4—C8—C9	0.9 (3)
C1—C2—C3—C4	−176.93 (18)	C7—N4—C8—Cl3	−177.03 (14)
N2—C2—C3—Cl1	−178.64 (15)	N4—C8—C9—C10	−0.1 (3)
C1—C2—C3—Cl1	4.4 (3)	Cl3—C8—C9—C10	177.81 (15)
C2—C3—C4—C5	1.0 (3)	C7—N3—C10—C9	0.1 (3)
Cl1—C3—C4—C5	179.68 (17)	C7—N3—C10—Cl4	179.59 (14)
C3—C4—C5—C6	−1.0 (3)	C8—C9—C10—N3	−0.5 (3)
C2—N2—C6—C5	0.9 (3)	C8—C9—C10—Cl4	−179.95 (15)
C2—N2—C6—Cl2	−178.40 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.09	2.937 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.09	2.937 (2)	170

Symmetry code: (i) .