Fluazinam.

In the asymmetric unit of the title compound {systematic name: 3-chloro-N-[3-chloro-5-(tri-fluoro-meth-yl)pyridin-2-yl]-2,6-di-nitro-4-(tri-fluoro-methyl)-aniline}, C13H4Cl2F6N4O4, which is the fungicide fluazinam, the dihedral angle between the pyridine and benzene ring planes is 42.20 (4)°. In the crystal, pairs of N-H⋯F hydrogen bonds link the mol-ecules into inversion dimers which are linked by C-Cl⋯π [Cl⋯ring centroid = 3.3618 (4) A °] and N-O⋯π [O⋯ring centroid = 3.1885 (16) Å] inter-actions into chains along [100]. In addition, short Cl⋯Cl, O⋯Cl, and F⋯F contacts [3.4676 (7), 3.2371 (13) and 2.7910 (15) Å] are present which connect the chains, yielding a three-dimensional network.

Related literature

For information on the toxicity and fungicidal properties of the title compound, see: Yoshida & Yukimoto (1993 ▶); Draper et al. (2003 ▶). For a related structure, see: McCullough et al. (1972 ▶).

Experimental

Crystal data

C13H4Cl2F6N4O4

M = 465.10

Triclinic,

a = 8.9546 (1) Å

b = 9.0724 (1) Å

c = 10.6818 (2) Å

α = 79.556 (1)°

β = 75.420 (1)°

γ = 83.451 (1)°

V = 823.79 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.49 mm−1

T = 173 K

0.30 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.867, T max = 0.930

15193 measured reflections

4096 independent reflections

3662 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.04

4096 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023210/kj2230sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023210/kj2230Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023210/kj2230Isup3.cml

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

C13H4Cl2F6N4O4	Z = 2
Mr = 465.10	F(000) = 460
Triclinic, P1	Dx = 1.875 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9546 (1) Å	Cell parameters from 8261 reflections
b = 9.0724 (1) Å	θ = 2.4–28.3°
c = 10.6818 (2) Å	µ = 0.49 mm−1
α = 79.556 (1)°	T = 173 K
β = 75.420 (1)°	Block, yellow
γ = 83.451 (1)°	0.30 × 0.18 × 0.15 mm
V = 823.79 (2) Å3

Bruker APEXII CCD detector diffractometer	4096 independent reflections
Radiation source: fine-focus sealed tube	3662 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −11→11
Tmin = 0.867, Tmax = 0.930	k = −12→10
15193 measured reflections	l = −14→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.3959P] where P = (Fo2 + 2Fc2)/3
4096 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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	0.83432 (5)	0.72367 (4)	0.34806 (4)	0.03069 (10)
Cl2	0.43809 (5)	0.32745 (5)	0.99480 (4)	0.03760 (11)
F1	1.06852 (11)	0.34123 (11)	0.15585 (9)	0.0342 (2)
F2	0.90981 (11)	0.53398 (12)	0.12664 (9)	0.0369 (2)
F3	1.11164 (11)	0.55470 (11)	0.19484 (10)	0.0357 (2)
F4	0.25749 (13)	−0.25110 (12)	0.84106 (12)	0.0484 (3)
F5	0.07528 (12)	−0.07681 (13)	0.86228 (14)	0.0542 (3)
F6	0.17049 (16)	−0.17401 (14)	1.02625 (11)	0.0572 (3)
N1	0.63148 (15)	0.61200 (13)	0.60382 (12)	0.0257 (3)
N2	0.82927 (13)	0.07922 (13)	0.58834 (12)	0.0239 (2)
N3	0.62868 (14)	0.31709 (14)	0.72658 (11)	0.0234 (2)
H3	0.6329	0.3764	0.7821	0.028*
N4	0.52522 (14)	0.10739 (14)	0.69279 (12)	0.0240 (2)
O1	0.51649 (16)	0.65800 (18)	0.56501 (17)	0.0595 (4)
O2	0.6693 (2)	0.65407 (19)	0.68990 (16)	0.0653 (5)
O3	0.83309 (13)	−0.01445 (12)	0.51781 (11)	0.0321 (2)
O4	0.84483 (13)	0.05111 (13)	0.70083 (11)	0.0321 (2)
C1	1.00024 (17)	0.46373 (17)	0.20469 (14)	0.0257 (3)
C2	0.90782 (15)	0.42479 (15)	0.34387 (13)	0.0210 (3)
C3	0.82543 (16)	0.53636 (15)	0.41309 (13)	0.0210 (3)
C4	0.73336 (15)	0.49449 (15)	0.53729 (13)	0.0209 (3)
C5	0.72421 (15)	0.34551 (15)	0.60148 (13)	0.0197 (3)
C6	0.81363 (15)	0.23826 (15)	0.53006 (13)	0.0204 (3)
C7	0.90021 (16)	0.27574 (15)	0.40317 (13)	0.0215 (3)
H7	0.9548	0.1987	0.3564	0.026*
C8	0.52749 (15)	0.20410 (15)	0.77180 (13)	0.0208 (3)
C9	0.42873 (16)	0.19730 (16)	0.89770 (14)	0.0238 (3)
C10	0.32506 (17)	0.08814 (17)	0.94103 (14)	0.0267 (3)
H10	0.2564	0.0818	1.0253	0.032*
C11	0.32343 (17)	−0.01298 (16)	0.85797 (15)	0.0257 (3)
C12	0.42492 (17)	0.00019 (16)	0.73578 (15)	0.0261 (3)
H12	0.4234	−0.0698	0.6800	0.031*
C13	0.20746 (19)	−0.12907 (18)	0.89734 (17)	0.0332 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0402 (2)	0.01712 (16)	0.03235 (19)	−0.00298 (13)	−0.00704 (15)	0.00063 (13)
Cl2	0.0392 (2)	0.0455 (2)	0.02904 (19)	−0.01359 (17)	0.00518 (15)	−0.02051 (17)
F1	0.0373 (5)	0.0320 (5)	0.0270 (4)	−0.0033 (4)	0.0067 (4)	−0.0076 (4)
F2	0.0418 (5)	0.0452 (6)	0.0211 (4)	0.0003 (4)	−0.0090 (4)	0.0013 (4)
F3	0.0328 (5)	0.0331 (5)	0.0372 (5)	−0.0146 (4)	−0.0007 (4)	0.0018 (4)
F4	0.0441 (6)	0.0303 (5)	0.0704 (8)	−0.0134 (4)	−0.0029 (5)	−0.0154 (5)
F5	0.0303 (5)	0.0468 (7)	0.0869 (9)	−0.0104 (5)	−0.0176 (6)	−0.0038 (6)
F6	0.0738 (8)	0.0510 (7)	0.0409 (6)	−0.0357 (6)	0.0012 (6)	0.0069 (5)
N1	0.0302 (6)	0.0191 (6)	0.0264 (6)	0.0011 (5)	−0.0048 (5)	−0.0047 (5)
N2	0.0218 (6)	0.0194 (6)	0.0264 (6)	−0.0010 (4)	0.0003 (4)	−0.0018 (5)
N3	0.0264 (6)	0.0231 (6)	0.0203 (5)	−0.0068 (4)	0.0004 (4)	−0.0074 (5)
N4	0.0246 (6)	0.0230 (6)	0.0237 (6)	−0.0033 (4)	−0.0018 (4)	−0.0067 (5)
O1	0.0400 (7)	0.0658 (10)	0.0874 (11)	0.0247 (7)	−0.0296 (8)	−0.0471 (9)
O2	0.0887 (12)	0.0629 (10)	0.0628 (10)	0.0380 (9)	−0.0454 (9)	−0.0464 (8)
O3	0.0366 (6)	0.0195 (5)	0.0370 (6)	−0.0018 (4)	0.0002 (5)	−0.0092 (4)
O4	0.0354 (6)	0.0287 (6)	0.0283 (6)	0.0002 (4)	−0.0075 (4)	0.0039 (4)
C1	0.0263 (7)	0.0261 (7)	0.0224 (7)	−0.0049 (5)	−0.0024 (5)	−0.0013 (5)
C2	0.0211 (6)	0.0221 (6)	0.0195 (6)	−0.0036 (5)	−0.0044 (5)	−0.0021 (5)
C3	0.0245 (6)	0.0168 (6)	0.0227 (6)	−0.0032 (5)	−0.0081 (5)	−0.0009 (5)
C4	0.0232 (6)	0.0184 (6)	0.0223 (6)	−0.0007 (5)	−0.0057 (5)	−0.0064 (5)
C5	0.0199 (6)	0.0205 (6)	0.0191 (6)	−0.0034 (5)	−0.0040 (5)	−0.0044 (5)
C6	0.0213 (6)	0.0175 (6)	0.0218 (6)	−0.0019 (5)	−0.0042 (5)	−0.0025 (5)
C7	0.0225 (6)	0.0199 (6)	0.0218 (6)	−0.0011 (5)	−0.0032 (5)	−0.0052 (5)
C8	0.0205 (6)	0.0200 (6)	0.0209 (6)	−0.0011 (5)	−0.0033 (5)	−0.0031 (5)
C9	0.0254 (7)	0.0250 (7)	0.0209 (6)	−0.0016 (5)	−0.0027 (5)	−0.0072 (5)
C10	0.0248 (7)	0.0299 (8)	0.0220 (7)	−0.0044 (6)	0.0000 (5)	−0.0020 (6)
C11	0.0246 (7)	0.0215 (7)	0.0296 (7)	−0.0035 (5)	−0.0054 (5)	−0.0005 (6)
C12	0.0268 (7)	0.0219 (7)	0.0298 (7)	−0.0030 (5)	−0.0046 (6)	−0.0070 (6)
C13	0.0321 (8)	0.0272 (8)	0.0377 (8)	−0.0090 (6)	−0.0032 (6)	−0.0014 (6)

Cl1—C3	1.7180 (13)	N4—C8	1.3280 (18)
Cl2—C9	1.7283 (14)	N4—C12	1.3391 (18)
F1—C1	1.3326 (17)	C1—C2	1.5090 (19)
F2—C1	1.3366 (17)	C2—C7	1.3868 (19)
F3—C1	1.3382 (17)	C2—C3	1.3936 (19)
F4—C13	1.334 (2)	C3—C4	1.3864 (19)
F5—C13	1.340 (2)	C4—C5	1.4017 (19)
F6—C13	1.330 (2)	C5—C6	1.3978 (18)
N1—O2	1.1911 (18)	C6—C7	1.3849 (18)
N1—O1	1.2084 (18)	C7—H7	0.9500
N1—C4	1.4834 (17)	C8—C9	1.4065 (19)
N2—O4	1.2220 (16)	C9—C10	1.373 (2)
N2—O3	1.2263 (16)	C10—C11	1.391 (2)
N2—C6	1.4701 (17)	C10—H10	0.9500
N3—C8	1.3846 (17)	C11—C12	1.384 (2)
N3—C5	1.3906 (17)	C11—C13	1.495 (2)
N3—H3	0.8800	C12—H12	0.9500
O2—N1—O1	125.30 (14)	C7—C6—C5	122.46 (12)
O2—N1—C4	117.99 (13)	C7—C6—N2	115.65 (12)
O1—N1—C4	116.71 (12)	C5—C6—N2	121.78 (12)
O4—N2—O3	125.24 (12)	C6—C7—C2	120.52 (13)
O4—N2—C6	117.51 (12)	C6—C7—H7	119.7
O3—N2—C6	117.15 (12)	C2—C7—H7	119.7
C8—N3—C5	126.00 (12)	N4—C8—N3	118.35 (12)
C8—N3—H3	117.0	N4—C8—C9	122.28 (13)
C5—N3—H3	117.0	N3—C8—C9	119.35 (12)
C8—N4—C12	118.20 (12)	C10—C9—C8	119.38 (13)
F1—C1—F2	107.50 (12)	C10—C9—Cl2	120.99 (11)
F1—C1—F3	107.14 (12)	C8—C9—Cl2	119.63 (11)
F2—C1—F3	106.99 (12)	C9—C10—C11	118.07 (13)
F1—C1—C2	111.51 (12)	C9—C10—H10	121.0
F2—C1—C2	111.11 (12)	C11—C10—H10	121.0
F3—C1—C2	112.33 (12)	C12—C11—C10	119.23 (13)
C7—C2—C3	119.09 (12)	C12—C11—C13	120.38 (14)
C7—C2—C1	119.92 (12)	C10—C11—C13	120.30 (14)
C3—C2—C1	120.96 (12)	N4—C12—C11	122.83 (14)
C4—C3—C2	118.91 (12)	N4—C12—H12	118.6
C4—C3—Cl1	119.39 (11)	C11—C12—H12	118.6
C2—C3—Cl1	121.70 (10)	F6—C13—F4	107.38 (14)
C3—C4—C5	123.74 (12)	F6—C13—F5	106.72 (14)
C3—C4—N1	118.60 (12)	F4—C13—F5	106.11 (14)
C5—C4—N1	117.56 (12)	F6—C13—C11	112.20 (14)
N3—C5—C6	126.22 (12)	F4—C13—C11	112.41 (13)
N3—C5—C4	118.65 (12)	F5—C13—C11	111.63 (13)
C6—C5—C4	115.13 (12)
F1—C1—C2—C7	−1.24 (18)	O3—N2—C6—C7	−41.24 (17)
F2—C1—C2—C7	118.67 (14)	O4—N2—C6—C5	−40.98 (18)
F3—C1—C2—C7	−121.52 (14)	O3—N2—C6—C5	142.43 (13)
F1—C1—C2—C3	−179.22 (12)	C5—C6—C7—C2	3.5 (2)
F2—C1—C2—C3	−59.31 (17)	N2—C6—C7—C2	−172.80 (12)
F3—C1—C2—C3	60.50 (17)	C3—C2—C7—C6	−0.9 (2)
C7—C2—C3—C4	−2.56 (19)	C1—C2—C7—C6	−178.88 (12)
C1—C2—C3—C4	175.44 (12)	C12—N4—C8—N3	−178.61 (13)
C7—C2—C3—Cl1	177.84 (10)	C12—N4—C8—C9	−0.1 (2)
C1—C2—C3—Cl1	−4.16 (18)	C5—N3—C8—N4	3.9 (2)
C2—C3—C4—C5	3.7 (2)	C5—N3—C8—C9	−174.67 (13)
Cl1—C3—C4—C5	−176.73 (10)	N4—C8—C9—C10	−0.5 (2)
C2—C3—C4—N1	−172.68 (12)	N3—C8—C9—C10	178.00 (13)
Cl1—C3—C4—N1	6.93 (17)	N4—C8—C9—Cl2	−179.84 (11)
O2—N1—C4—C3	−104.70 (18)	N3—C8—C9—Cl2	−1.30 (19)
O1—N1—C4—C3	74.84 (19)	C8—C9—C10—C11	0.6 (2)
O2—N1—C4—C5	78.73 (19)	Cl2—C9—C10—C11	179.93 (11)
O1—N1—C4—C5	−101.72 (17)	C9—C10—C11—C12	−0.2 (2)
C8—N3—C5—C6	−43.9 (2)	C9—C10—C11—C13	−176.82 (14)
C8—N3—C5—C4	135.41 (14)	C8—N4—C12—C11	0.5 (2)
C3—C4—C5—N3	179.48 (12)	C10—C11—C12—N4	−0.4 (2)
N1—C4—C5—N3	−4.14 (18)	C13—C11—C12—N4	176.21 (14)
C3—C4—C5—C6	−1.2 (2)	C12—C11—C13—F6	151.47 (15)
N1—C4—C5—C6	175.22 (12)	C10—C11—C13—F6	−31.9 (2)
N3—C5—C6—C7	176.86 (13)	C12—C11—C13—F4	30.3 (2)
C4—C5—C6—C7	−2.45 (19)	C10—C11—C13—F4	−153.10 (14)
N3—C5—C6—N2	−7.1 (2)	C12—C11—C13—F5	−88.78 (18)
C4—C5—C6—N2	173.63 (12)	C10—C11—C13—F5	87.80 (19)
O4—N2—C6—C7	135.34 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···F3i	0.88	2.52	3.0690 (15)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯F3i	0.88	2.52	3.0690 (15)	121

Symmetry code: (i) .