2,3,6-Trichloro-5-(trichloro-meth-yl)pyridine.

The title compound, C(6)HCl(6)N, lies on a mirror plane, the asymmetric unit conataining a half-mol-ecule. Weak intra-molecular C-H⋯Cl contacts are observed.

Related literature

For biological background, see: Okorley & Dietsche (1988 ▶). For the synthetic procedure, see: Allphin et al. (1993 ▶); For a related structure, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C6HCl6N

M = 299.78

Orthorhombic,

a = 8.3100 (17) Å

b = 17.018 (3) Å

c = 7.3160 (15) Å

V = 1034.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.61 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.644, T max = 0.739

1985 measured reflections

1033 independent reflections

779 reflections with I > 2σ(I)

R int = 0.063

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.123

S = 1.01

1033 reflections

77 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812035404/pv2577sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035404/pv2577Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035404/pv2577Isup3.cml

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

C6HCl6N	F(000) = 584
Mr = 299.78	Dx = 1.925 Mg m−3
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2b	Cell parameters from 25 reflections
a = 8.3100 (17) Å	θ = 10–13°
b = 17.018 (3) Å	µ = 1.61 mm−1
c = 7.3160 (15) Å	T = 293 K
V = 1034.6 (4) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	779 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Graphite monochromator	θmax = 25.4°, θmin = 2.4°
ω/2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = −20→0
Tmin = 0.644, Tmax = 0.739	l = −8→0
1985 measured reflections	3 standard reflections every 200 reflections
1033 independent reflections	intensity decay: 1%

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.078P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
1033 reflections	Δρmax = 0.26 e Å−3
77 parameters	Δρmin = −0.39 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: 0.077 (6)

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
N	0.5025 (5)	0.4324 (2)	0.2500	0.0467 (9)
Cl1	0.8417 (2)	0.26884 (8)	0.2500	0.0806 (6)
C1	0.8339 (6)	0.4268 (3)	0.2500	0.0478 (11)
H1A	0.9457	0.4241	0.2500	0.057*
Cl2	0.45826 (19)	0.28195 (8)	0.2500	0.0753 (5)
C2	0.7445 (7)	0.3584 (3)	0.2500	0.0537 (12)
Cl3	0.47402 (13)	0.58193 (7)	0.2500	0.0569 (4)
C3	0.5783 (6)	0.3642 (3)	0.2500	0.0486 (11)
Cl4	0.81252 (10)	0.63147 (5)	0.05227 (15)	0.0619 (4)
C4	0.5902 (5)	0.4969 (2)	0.2500	0.0399 (10)
Cl5	1.06686 (13)	0.55710 (8)	0.2500	0.0672 (5)
C5	0.7586 (5)	0.4991 (2)	0.2500	0.0418 (10)
C6	0.8554 (5)	0.5748 (2)	0.2500	0.0451 (11)

	U11	U22	U33	U12	U13	U23
N	0.0472 (18)	0.042 (2)	0.051 (2)	−0.0058 (15)	0.000	0.000
Cl1	0.1128 (13)	0.0423 (7)	0.0867 (11)	0.0263 (7)	0.000	0.000
C1	0.051 (3)	0.042 (2)	0.051 (3)	0.0113 (19)	0.000	0.000
Cl2	0.0977 (11)	0.0433 (7)	0.0849 (10)	−0.0220 (6)	0.000	0.000
C2	0.075 (3)	0.042 (2)	0.044 (2)	0.014 (2)	0.000	0.000
Cl3	0.0372 (6)	0.0463 (7)	0.0872 (10)	0.0073 (4)	0.000	0.000
C3	0.061 (3)	0.043 (2)	0.042 (2)	−0.009 (2)	0.000	0.000
Cl4	0.0572 (5)	0.0552 (6)	0.0734 (7)	0.0006 (3)	0.0064 (5)	0.0182 (4)
C4	0.039 (2)	0.034 (2)	0.046 (2)	0.0056 (17)	0.000	0.000
Cl5	0.0334 (6)	0.0666 (8)	0.1018 (12)	0.0007 (5)	0.000	0.000
C5	0.041 (2)	0.040 (2)	0.044 (2)	−0.0008 (18)	0.000	0.000
C6	0.036 (2)	0.039 (2)	0.061 (3)	0.0008 (17)	0.000	0.000

N—C4	1.318 (6)	C2—C3	1.385 (8)
N—C3	1.321 (6)	Cl3—C4	1.739 (4)
Cl1—C2	1.724 (5)	Cl4—C6	1.774 (3)
C1—C2	1.381 (7)	C4—C5	1.400 (6)
C1—C5	1.381 (6)	Cl5—C6	1.783 (5)
C1—H1A	0.9300	C5—C6	1.519 (6)
Cl2—C3	1.719 (4)	C6—Cl4i	1.774 (3)
C4—N—C3	118.0 (4)	N—C4—Cl3	112.7 (3)
C2—C1—C5	120.5 (4)	C5—C4—Cl3	122.2 (3)
C2—C1—H1A	119.7	C1—C5—C4	115.4 (4)
C5—C1—H1A	119.7	C1—C5—C6	121.1 (4)
C1—C2—C3	118.4 (4)	C4—C5—C6	123.5 (4)
C1—C2—Cl1	119.6 (4)	C5—C6—Cl4	110.77 (18)
C3—C2—Cl1	122.0 (4)	C5—C6—Cl4i	110.77 (18)
N—C3—C2	122.6 (4)	Cl4—C6—Cl4i	109.2 (2)
N—C3—Cl2	116.0 (4)	C5—C6—Cl5	112.2 (3)
C2—C3—Cl2	121.4 (4)	Cl4—C6—Cl5	106.84 (17)
N—C4—C5	125.1 (4)	Cl4i—C6—Cl5	106.84 (17)
C5—C1—C2—C3	0.0	C2—C1—C5—C6	180.0
C5—C1—C2—Cl1	180.0	N—C4—C5—C1	0.0
C4—N—C3—C2	0.0	Cl3—C4—C5—C1	180.0
C4—N—C3—Cl2	180.0	N—C4—C5—C6	180.0
C1—C2—C3—N	0.0	Cl3—C4—C5—C6	0.0
Cl1—C2—C3—N	180.0	C1—C5—C6—Cl4	119.32 (19)
C1—C2—C3—Cl2	180.0	C4—C5—C6—Cl4	−60.68 (19)
Cl1—C2—C3—Cl2	0.0	C1—C5—C6—Cl4i	−119.32 (19)
C3—N—C4—C5	0.0	C4—C5—C6—Cl4i	60.68 (19)
C3—N—C4—Cl3	180.0	C1—C5—C6—Cl5	0.0
C2—C1—C5—C4	0.0	C4—C5—C6—Cl5	180.0

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl5	0.93	2.48	2.944 (5)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cl5	0.93	2.48	2.944 (5)	111