2,7-Bis-(trichloro-meth-yl)-1,8-naphthyridine.

The complete mol-ecule of the title compound, C(10)H(4)Cl(6)N(2), is generated by crystallographic twofold symmetry, with two C atoms lying on the rotation axis; the 1,8-naphthyridine ring is almost planar with an r.m.s. deviation of 0.0002 Å. In the crystal structure, the mol-ecules are stacked in an anti-parallel manner along [001]. Short Cl⋯Cl [3.3502 (4)] and Cl⋯N [3.2004 (11)-3.2220 (10) Å] contacts are observed in the crystal structure.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For graph-set notation of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2009 ▶); Wang et al. (2008 ▶). For background to the properties and applications of 1,8-naphthyridines, see: Braccio et al. (2008 ▶); Chen et al. (2001 ▶); Ferrarini et al. (1998 ▶; 2000 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H4Cl6N2

M = 364.85

Monoclinic,

a = 19.9154 (4) Å

b = 6.5977 (1) Å

c = 10.5975 (2) Å

β = 111.483 (2)°

V = 1295.73 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.30 mm−1

T = 100 K

0.40 × 0.26 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.624, T max = 0.944

28872 measured reflections

4010 independent reflections

3136 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.089

S = 1.05

4010 reflections

91 parameters

All H-atom parameters refined

Δρmax = 0.64 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005234/hb5307sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005234/hb5307Isup2.hkl

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

C10H4Cl6N2	F(000) = 720
Mr = 364.85	Dx = 1.870 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4010 reflections
a = 19.9154 (4) Å	θ = 2.2–40.0°
b = 6.5977 (1) Å	µ = 1.30 mm−1
c = 10.5975 (2) Å	T = 100 K
β = 111.483 (2)°	Slab, colorless
V = 1295.73 (4) Å3	0.40 × 0.26 × 0.05 mm
Z = 4

Bruker APEXII CCD diffractometer	4010 independent reflections
Radiation source: sealed tube	3136 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 40.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −36→34
Tmin = 0.624, Tmax = 0.944	k = −11→11
28872 measured reflections	l = −18→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.889P] where P = (Fo2 + 2Fc2)/3
4010 reflections	(Δ/σ)max = 0.002
91 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	0.090117 (15)	0.01827 (4)	1.12884 (3)	0.01585 (6)
Cl2	0.194324 (15)	0.02817 (4)	0.99732 (3)	0.01645 (6)
Cl3	0.202697 (15)	0.31574 (4)	1.20815 (3)	0.01848 (6)
N1	0.04657 (5)	0.21807 (14)	0.85379 (9)	0.01358 (15)
C1	0.09721 (6)	0.53166 (17)	0.96675 (12)	0.01599 (18)
C2	0.09266 (6)	0.31794 (16)	0.95656 (11)	0.01302 (16)
C3	0.0000	0.3281 (2)	0.7500	0.0124 (2)
C4	0.0000	0.5430 (2)	0.7500	0.0136 (2)
C5	−0.05049 (6)	0.64457 (17)	0.63741 (11)	0.01611 (18)
C6	0.14272 (6)	0.17959 (16)	1.06796 (10)	0.01333 (16)
H6	−0.0513 (10)	0.788 (3)	0.6355 (18)	0.021 (4)*
H1	0.1292 (10)	0.598 (3)	1.038 (2)	0.024 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01798 (11)	0.01518 (11)	0.01362 (10)	−0.00263 (8)	0.00487 (8)	0.00164 (8)
Cl2	0.01578 (11)	0.01700 (12)	0.01533 (11)	0.00202 (8)	0.00425 (8)	0.00040 (8)
Cl3	0.02005 (12)	0.01629 (11)	0.01330 (11)	−0.00383 (9)	−0.00076 (8)	−0.00181 (8)
N1	0.0155 (4)	0.0114 (3)	0.0115 (3)	−0.0004 (3)	0.0021 (3)	0.0002 (3)
C1	0.0186 (4)	0.0110 (4)	0.0152 (4)	−0.0022 (3)	0.0025 (4)	−0.0012 (3)
C2	0.0145 (4)	0.0113 (4)	0.0123 (4)	−0.0008 (3)	0.0038 (3)	0.0001 (3)
C3	0.0137 (5)	0.0101 (5)	0.0117 (5)	0.000	0.0027 (4)	0.000
C4	0.0173 (6)	0.0095 (5)	0.0132 (5)	0.000	0.0045 (5)	0.000
C5	0.0198 (5)	0.0104 (4)	0.0155 (4)	0.0011 (3)	0.0033 (4)	0.0009 (3)
C6	0.0148 (4)	0.0122 (4)	0.0113 (4)	−0.0015 (3)	0.0028 (3)	−0.0007 (3)

Cl1—C6	1.7725 (11)	C2—C6	1.5358 (15)
Cl2—C6	1.7827 (11)	C3—N1i	1.3602 (12)
Cl3—C6	1.7723 (10)	C3—C4	1.418 (2)
N1—C2	1.3156 (14)	C4—C5	1.4160 (13)
N1—C3	1.3602 (12)	C4—C5i	1.4160 (13)
C1—C5i	1.3736 (16)	C5—C1i	1.3737 (16)
C1—C2	1.4145 (15)	C5—H6	0.95 (2)
C1—H1	0.90 (2)
C2—N1—C3	117.68 (10)	C5—C4—C3	118.24 (7)
C5i—C1—C2	118.28 (10)	C5i—C4—C3	118.24 (7)
C5i—C1—H1	118.1 (14)	C1i—C5—C4	118.91 (11)
C2—C1—H1	123.6 (14)	C1i—C5—H6	121.6 (11)
N1—C2—C1	124.62 (10)	C4—C5—H6	119.5 (11)
N1—C2—C6	113.48 (9)	C2—C6—Cl3	113.05 (7)
C1—C2—C6	121.90 (9)	C2—C6—Cl1	109.44 (7)
N1—C3—N1i	115.46 (13)	Cl3—C6—Cl1	107.82 (6)
N1—C3—C4	122.27 (6)	C2—C6—Cl2	108.79 (7)
N1i—C3—C4	122.27 (6)	Cl3—C6—Cl2	108.72 (6)
C5—C4—C5i	123.51 (14)	Cl1—C6—Cl2	108.95 (6)
C3—N1—C2—C1	0.00 (16)	N1i—C3—C4—C5i	179.98 (8)
C3—N1—C2—C6	−179.95 (8)	C5i—C4—C5—C1i	180.00 (13)
C5i—C1—C2—N1	−0.02 (19)	C3—C4—C5—C1i	0.00 (13)
C5i—C1—C2—C6	179.92 (11)	N1—C2—C6—Cl3	−178.20 (8)
C2—N1—C3—N1i	−179.98 (11)	C1—C2—C6—Cl3	1.85 (14)
C2—N1—C3—C4	0.02 (11)	N1—C2—C6—Cl1	−58.01 (11)
N1—C3—C4—C5	179.98 (8)	C1—C2—C6—Cl1	122.04 (10)
N1i—C3—C4—C5	−0.02 (8)	N1—C2—C6—Cl2	60.93 (11)
N1—C3—C4—C5i	−0.02 (8)	C1—C2—C6—Cl2	−119.02 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl3	0.90 (2)	2.63 (2)	3.0085 (12)	106.0 (14)