N-{N-[5-(2,4-Dichloro-phen-yl)-1,3,4-thia-diazol-2-yl]carbamo-yl}-2,6-difluoro-benzamide.

In the title compound, C(16)H(8)Cl(2)F(2)N(4)O(2)S, the thia-diazole ring makes dihedral angles of 24.94 (14) and 48.11 (14)°, respectively, with the dichloro- and difluoro-substituted benzene rings. An intra-molecular N-H⋯O hydrogen bond results in the formation of a planar (mean deviation 0.0091 Å) six-membered ring. In the crystal structure, mol-ecules form centrosymmetric dimers through pairs of inter-molecular N-H⋯O hydrogen bonds.

Related literature

For 1,3,4-thia­diazole aryl­urea derivatives, see: Hajjar & Casida (1978 ▶); Leighton et al. (1981 ▶); Metcalf et al. (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H8Cl2F2N4O2S

M = 429.22

Monoclinic,

a = 8.1600 (16) Å

b = 7.6100 (15) Å

c = 27.102 (5) Å

β = 92.42 (3)°

V = 1681.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.55 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 = 0.852, T max = 0.898

5228 measured reflections

3053 independent reflections

2195 reflections with I > 2σ(I)

R int = 0.034

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.01

3053 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044584/is2477sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044584/is2477Isup2.hkl

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

C16H8Cl2F2N4O2S	F(000) = 864
Mr = 429.22	Dx = 1.696 Mg m−3
Monoclinic, P21/c	Melting point: 498 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.1600 (16) Å	Cell parameters from 25 reflections
b = 7.6100 (15) Å	θ = 10–13°
c = 27.102 (5) Å	µ = 0.55 mm−1
β = 92.42 (3)°	T = 293 K
V = 1681.5 (6) Å3	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	2195 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 25.3°, θmin = 1.5°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −4→9
Tmin = 0.852, Tmax = 0.898	l = −32→32
5228 measured reflections	3 standard reflections every 200 reflections
3053 independent reflections	intensity decay: 1%

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
3053 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.30 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
S	0.24677 (10)	0.99323 (10)	0.44933 (3)	0.0422 (2)
Cl1	0.07127 (15)	1.02058 (11)	0.34523 (3)	0.0704 (3)
Cl2	−0.13977 (11)	1.65344 (11)	0.29072 (3)	0.0557 (3)
F1	0.6408 (2)	0.7102 (3)	0.70051 (7)	0.0601 (5)
F2	0.4085 (3)	0.2644 (2)	0.60078 (7)	0.0616 (5)
O1	0.3906 (3)	0.7670 (3)	0.63370 (8)	0.0534 (6)
O2	0.3952 (3)	0.6786 (3)	0.48524 (7)	0.0584 (7)
N1	0.4499 (3)	0.6085 (3)	0.56566 (8)	0.0433 (6)
H1A	0.4957	0.5131	0.5562	0.052*
N2	0.3126 (3)	0.8663 (3)	0.54369 (9)	0.0419 (6)
H2A	0.3102	0.8843	0.5750	0.050*
N3	0.1602 (3)	1.1185 (3)	0.53201 (9)	0.0429 (6)
N4	0.0980 (3)	1.2319 (3)	0.49659 (9)	0.0433 (6)
C1	0.6387 (4)	0.2440 (5)	0.71587 (13)	0.0592 (10)
H1B	0.6765	0.1602	0.7386	0.071*
C2	0.5527 (4)	0.1908 (4)	0.67364 (13)	0.0526 (9)
H2B	0.5324	0.0724	0.6675	0.063*
C3	0.4981 (4)	0.3162 (4)	0.64105 (11)	0.0432 (7)
C4	0.5219 (3)	0.4949 (4)	0.64808 (10)	0.0372 (7)
C5	0.6099 (4)	0.5392 (4)	0.69135 (11)	0.0447 (8)
C6	0.6695 (4)	0.4191 (5)	0.72498 (12)	0.0557 (9)
H6A	0.7292	0.4546	0.7532	0.067*
C7	0.4482 (4)	0.6364 (4)	0.61606 (10)	0.0390 (7)
C8	0.3853 (4)	0.7180 (4)	0.52848 (11)	0.0417 (7)
C9	0.2414 (3)	0.9916 (4)	0.51268 (10)	0.0363 (7)
C10	0.1319 (3)	1.1852 (4)	0.45196 (10)	0.0359 (7)
C11	0.0728 (3)	1.2949 (4)	0.40993 (10)	0.0366 (7)
C12	0.0397 (4)	1.2367 (4)	0.36183 (11)	0.0381 (7)
C13	−0.0232 (4)	1.3465 (4)	0.32543 (11)	0.0425 (7)
H13A	−0.0431	1.3052	0.2934	0.051*
C14	−0.0561 (4)	1.5183 (4)	0.33714 (10)	0.0395 (7)
C15	−0.0260 (4)	1.5824 (4)	0.38409 (11)	0.0481 (8)
H15A	−0.0488	1.6988	0.3916	0.058*
C16	0.0386 (4)	1.4703 (4)	0.41965 (11)	0.0455 (8)
H16A	0.0601	1.5134	0.4514	0.055*

	U11	U22	U33	U12	U13	U23
S	0.0482 (5)	0.0403 (5)	0.0384 (4)	0.0116 (4)	0.0050 (3)	−0.0003 (3)
Cl1	0.1326 (9)	0.0327 (5)	0.0451 (5)	0.0130 (5)	−0.0047 (5)	−0.0082 (4)
Cl2	0.0709 (6)	0.0489 (5)	0.0469 (5)	0.0135 (4)	−0.0026 (4)	0.0082 (4)
F1	0.0674 (13)	0.0525 (12)	0.0589 (12)	−0.0073 (10)	−0.0146 (10)	−0.0105 (9)
F2	0.0766 (14)	0.0489 (12)	0.0578 (12)	−0.0075 (10)	−0.0145 (10)	−0.0106 (9)
O1	0.0714 (16)	0.0449 (14)	0.0436 (12)	0.0189 (12)	0.0004 (11)	−0.0060 (10)
O2	0.0841 (17)	0.0548 (15)	0.0363 (12)	0.0297 (13)	0.0035 (11)	−0.0017 (10)
N1	0.0530 (16)	0.0385 (15)	0.0382 (13)	0.0141 (12)	−0.0017 (11)	−0.0005 (11)
N2	0.0498 (15)	0.0402 (15)	0.0354 (13)	0.0098 (12)	−0.0024 (11)	−0.0021 (11)
N3	0.0494 (15)	0.0373 (15)	0.0415 (14)	0.0091 (12)	−0.0035 (12)	−0.0026 (12)
N4	0.0510 (16)	0.0396 (15)	0.0390 (14)	0.0107 (12)	−0.0015 (12)	−0.0031 (11)
C1	0.062 (2)	0.064 (3)	0.052 (2)	0.0136 (19)	−0.0012 (18)	0.0170 (18)
C2	0.055 (2)	0.0393 (19)	0.064 (2)	0.0022 (16)	0.0085 (17)	0.0071 (16)
C3	0.0423 (17)	0.0447 (19)	0.0427 (17)	−0.0009 (15)	0.0026 (13)	−0.0031 (14)
C4	0.0361 (15)	0.0392 (17)	0.0363 (15)	−0.0001 (13)	0.0028 (12)	−0.0007 (13)
C5	0.0415 (18)	0.048 (2)	0.0449 (17)	−0.0003 (15)	0.0009 (14)	−0.0045 (15)
C6	0.055 (2)	0.065 (2)	0.0464 (19)	0.0020 (18)	−0.0079 (16)	0.0048 (17)
C7	0.0402 (16)	0.0381 (17)	0.0386 (16)	0.0004 (14)	−0.0009 (13)	−0.0042 (13)
C8	0.0433 (17)	0.0418 (18)	0.0399 (17)	0.0086 (14)	0.0011 (14)	0.0004 (14)
C9	0.0378 (16)	0.0343 (16)	0.0365 (15)	0.0011 (13)	−0.0032 (12)	−0.0050 (13)
C10	0.0385 (16)	0.0279 (15)	0.0410 (16)	0.0011 (13)	−0.0003 (13)	−0.0042 (12)
C11	0.0399 (16)	0.0315 (16)	0.0387 (15)	0.0019 (13)	0.0052 (13)	−0.0024 (13)
C12	0.0456 (17)	0.0281 (16)	0.0408 (16)	0.0000 (13)	0.0056 (13)	−0.0062 (12)
C13	0.0507 (18)	0.0406 (18)	0.0360 (15)	0.0008 (15)	0.0001 (13)	−0.0035 (14)
C14	0.0420 (17)	0.0375 (18)	0.0393 (16)	0.0009 (14)	0.0055 (13)	0.0025 (13)
C15	0.069 (2)	0.0321 (17)	0.0429 (17)	0.0119 (16)	0.0016 (15)	−0.0034 (14)
C16	0.063 (2)	0.0365 (18)	0.0368 (16)	0.0031 (16)	0.0006 (14)	−0.0060 (13)

S—C9	1.719 (3)	C1—H1B	0.9300
S—C10	1.738 (3)	C2—C3	1.362 (4)
Cl1—C12	1.727 (3)	C2—H2B	0.9300
Cl2—C14	1.742 (3)	C3—C4	1.386 (4)
F1—C5	1.347 (4)	C4—C5	1.390 (4)
F2—C3	1.347 (4)	C4—C7	1.494 (4)
O1—C7	1.206 (3)	C5—C6	1.365 (4)
O2—C8	1.216 (3)	C6—H6A	0.9300
N1—C7	1.383 (4)	C10—C11	1.477 (4)
N1—C8	1.394 (4)	C11—C16	1.391 (4)
N1—H1A	0.8600	C11—C12	1.393 (4)
N2—C8	1.348 (4)	C12—C13	1.375 (4)
N2—C9	1.383 (4)	C13—C14	1.375 (4)
N2—H2A	0.8600	C13—H13A	0.9300
N3—C9	1.294 (3)	C14—C15	1.375 (4)
N3—N4	1.372 (3)	C15—C16	1.375 (4)
N4—C10	1.302 (4)	C15—H15A	0.9300
C1—C6	1.376 (5)	C16—H16A	0.9300
C1—C2	1.378 (5)
C9—S—C10	85.91 (14)	N1—C7—C4	116.3 (3)
C7—N1—C8	127.1 (3)	O2—C8—N2	123.3 (3)
C7—N1—H1A	116.5	O2—C8—N1	120.7 (3)
C8—N1—H1A	116.5	N2—C8—N1	115.9 (3)
C8—N2—C9	124.8 (2)	N3—C9—N2	118.5 (2)
C8—N2—H2A	117.6	N3—C9—S	115.7 (2)
C9—N2—H2A	117.6	N2—C9—S	125.7 (2)
C9—N3—N4	111.5 (2)	N4—C10—C11	119.1 (3)
C10—N4—N3	113.0 (2)	N4—C10—S	113.8 (2)
C6—C1—C2	121.1 (3)	C11—C10—S	127.1 (2)
C6—C1—H1B	119.5	C16—C11—C12	116.7 (3)
C2—C1—H1B	119.5	C16—C11—C10	117.3 (3)
C3—C2—C1	118.3 (3)	C12—C11—C10	125.9 (3)
C3—C2—H2B	120.9	C13—C12—C11	122.0 (3)
C1—C2—H2B	120.9	C13—C12—Cl1	116.5 (2)
F2—C3—C2	118.1 (3)	C11—C12—Cl1	121.4 (2)
F2—C3—C4	117.8 (3)	C12—C13—C14	118.9 (3)
C2—C3—C4	123.9 (3)	C12—C13—H13A	120.6
C3—C4—C5	114.7 (3)	C14—C13—H13A	120.6
C3—C4—C7	125.2 (3)	C15—C14—C13	121.5 (3)
C5—C4—C7	119.8 (3)	C15—C14—Cl2	120.5 (2)
F1—C5—C6	117.7 (3)	C13—C14—Cl2	118.0 (2)
F1—C5—C4	118.4 (3)	C14—C15—C16	118.5 (3)
C6—C5—C4	123.9 (3)	C14—C15—H15A	120.8
C5—C6—C1	118.1 (3)	C16—C15—H15A	120.8
C5—C6—H6A	121.0	C15—C16—C11	122.4 (3)
C1—C6—H6A	121.0	C15—C16—H16A	118.8
O1—C7—N1	122.6 (3)	C11—C16—H16A	118.8
O1—C7—C4	121.2 (3)
C9—N3—N4—C10	1.1 (4)	N4—N3—C9—S	−1.6 (3)
C6—C1—C2—C3	−0.2 (5)	C8—N2—C9—N3	172.6 (3)
C1—C2—C3—F2	−177.4 (3)	C8—N2—C9—S	−5.9 (4)
C1—C2—C3—C4	−0.9 (5)	C10—S—C9—N3	1.2 (2)
F2—C3—C4—C5	177.6 (3)	C10—S—C9—N2	179.8 (3)
C2—C3—C4—C5	1.0 (5)	N3—N4—C10—C11	180.0 (3)
F2—C3—C4—C7	3.7 (5)	N3—N4—C10—S	−0.2 (3)
C2—C3—C4—C7	−172.8 (3)	C9—S—C10—N4	−0.5 (2)
C3—C4—C5—F1	178.9 (3)	C9—S—C10—C11	179.3 (3)
C7—C4—C5—F1	−6.9 (4)	N4—C10—C11—C16	23.2 (4)
C3—C4—C5—C6	−0.1 (5)	S—C10—C11—C16	−156.5 (2)
C7—C4—C5—C6	174.2 (3)	N4—C10—C11—C12	−153.1 (3)
F1—C5—C6—C1	−179.9 (3)	S—C10—C11—C12	27.1 (4)
C4—C5—C6—C1	−0.9 (5)	C16—C11—C12—C13	0.2 (4)
C2—C1—C6—C5	1.1 (5)	C10—C11—C12—C13	176.6 (3)
C8—N1—C7—O1	−1.6 (5)	C16—C11—C12—Cl1	−178.2 (2)
C8—N1—C7—C4	178.2 (3)	C10—C11—C12—Cl1	−1.9 (4)
C3—C4—C7—O1	136.8 (3)	C11—C12—C13—C14	−0.8 (5)
C5—C4—C7—O1	−36.8 (4)	Cl1—C12—C13—C14	177.7 (2)
C3—C4—C7—N1	−43.1 (4)	C12—C13—C14—C15	0.6 (5)
C5—C4—C7—N1	143.3 (3)	C12—C13—C14—Cl2	−178.7 (2)
C9—N2—C8—O2	−0.3 (5)	C13—C14—C15—C16	0.0 (5)
C9—N2—C8—N1	179.9 (3)	Cl2—C14—C15—C16	179.3 (2)
C7—N1—C8—O2	179.7 (3)	C14—C15—C16—C11	−0.6 (5)
C7—N1—C8—N2	−0.5 (5)	C12—C11—C16—C15	0.5 (5)
N4—N3—C9—N2	179.8 (3)	C10—C11—C16—C15	−176.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.07	2.902 (3)	164
N2—H2A···O1	0.86	1.92	2.607 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.07	2.902 (3)	164
N2—H2A⋯O1	0.86	1.92	2.607 (3)	136

Symmetry code: (i) .