N-(5-Chloro-1,3-thia-zol-2-yl)-2,4-difluoro-benzamide.

The title compound, C(10)H(5)ClF(2)N(2)OS, was obtained by linking an amino heterocycle and a substituted benzoyl chloride. The dihedral angle between the two rings is 41.2 (2)° and the equalization of the amide C-N bond lengths reveals the existence of conjugation between the benzene ring and the thia-zole unit. In the crystal, pairs of N-H⋯N hydrogen bonds link mol-ecules into inversion dimers. Non-classical C-H⋯F and C-H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For synthesis and the biological activity of thia­zolides, see: Ballard et al. (2011 ▶).

Experimental

Crystal data

C10H5ClF2N2OS

M = 274.68

Triclinic,

a = 6.929 (2) Å

b = 7.330 (2) Å

c = 12.179 (4) Å

α = 101.669 (3)°

β = 98.277 (3)°

γ = 111.796 (3)°

V = 545.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.55 mm−1

T = 296 K

0.35 × 0.33 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.831, T max = 0.866

3930 measured reflections

1998 independent reflections

1693 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.136

S = 1.06

1998 reflections

155 parameters

H-atom parameters constrained

Δρmax = 1.25 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812022477/rk2350sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022477/rk2350Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812022477/rk2350Isup3.cml

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

C10H5ClF2N2OS	Z = 2
Mr = 274.68	F(000) = 276
Triclinic, P1	Dx = 1.671 Mg m−3
Hall symbol: -P 1	Melting point = 428–429 K
a = 6.929 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.330 (2) Å	Cell parameters from 2870 reflections
c = 12.179 (4) Å	θ = 3.1–28.2°
α = 101.669 (3)°	µ = 0.55 mm−1
β = 98.277 (3)°	T = 296 K
γ = 111.796 (3)°	Block, colourless
V = 545.9 (3) Å3	0.35 × 0.33 × 0.27 mm

Bruker APEXII CCD diffractometer	1998 independent reflections
Radiation source: fine-focus sealed tube	1693 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ– and ω–scans	θmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.831, Tmax = 0.866	k = −8→8
3930 measured reflections	l = −14→14

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0689P)2 + 0.4949P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1998 reflections	Δρmax = 1.25 e Å−3
155 parameters	Δρmin = −0.33 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: 0.53 (3)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	1.0517 (5)	0.7233 (5)	0.9365 (3)	0.0438 (7)
C2	1.2260 (5)	0.8083 (5)	1.0282 (3)	0.0494 (8)
H2	1.2296	0.8968	1.0958	0.059*
C3	1.3958 (5)	0.7579 (5)	1.0168 (3)	0.0467 (8)
C4	1.3945 (5)	0.6268 (5)	0.9182 (3)	0.0464 (7)
H4	1.5116	0.5954	0.9126	0.056*
C5	1.2153 (5)	0.5432 (5)	0.8280 (3)	0.0413 (7)
H5	1.2120	0.4530	0.7612	0.050*
C6	1.0387 (4)	0.5896 (4)	0.8336 (2)	0.0358 (6)
C7	0.8392 (5)	0.4900 (4)	0.7407 (2)	0.0390 (7)
C8	0.6940 (4)	0.3522 (4)	0.5350 (2)	0.0365 (6)
C9	0.5284 (5)	0.2099 (5)	0.3514 (3)	0.0505 (8)
H9	0.5166	0.1733	0.2722	0.061*
C10	0.3587 (5)	0.1551 (4)	0.3969 (3)	0.0447 (7)
Cl1	0.09389 (14)	0.01753 (14)	0.32522 (8)	0.0662 (4)
F1	1.5714 (3)	0.8434 (3)	1.10528 (18)	0.0673 (6)
F2	0.8890 (3)	0.7783 (4)	0.9458 (2)	0.0796 (8)
N1	0.8646 (4)	0.4602 (4)	0.62983 (19)	0.0376 (6)
H1	0.9916	0.5106	0.6191	0.045*
N2	0.7224 (4)	0.3246 (4)	0.4302 (2)	0.0449 (6)
O3	0.6609 (3)	0.4314 (4)	0.75914 (18)	0.0553 (6)
S1	0.43196 (11)	0.24360 (11)	0.54607 (6)	0.0421 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0358 (15)	0.0438 (16)	0.0480 (17)	0.0122 (13)	0.0149 (13)	0.0095 (13)
C2	0.0483 (18)	0.0462 (17)	0.0386 (16)	0.0079 (14)	0.0089 (14)	0.0038 (13)
C3	0.0365 (15)	0.0494 (18)	0.0420 (16)	0.0035 (13)	0.0018 (12)	0.0198 (14)
C4	0.0377 (15)	0.0559 (19)	0.0504 (18)	0.0196 (14)	0.0119 (14)	0.0236 (15)
C5	0.0396 (15)	0.0447 (16)	0.0393 (15)	0.0156 (13)	0.0128 (12)	0.0123 (13)
C6	0.0329 (13)	0.0370 (14)	0.0339 (14)	0.0084 (11)	0.0107 (11)	0.0119 (11)
C7	0.0377 (15)	0.0413 (15)	0.0368 (15)	0.0135 (12)	0.0117 (12)	0.0121 (12)
C8	0.0339 (13)	0.0349 (14)	0.0372 (14)	0.0094 (11)	0.0101 (11)	0.0110 (11)
C9	0.0490 (18)	0.0455 (17)	0.0361 (16)	0.0020 (14)	0.0049 (13)	0.0052 (13)
C10	0.0414 (16)	0.0335 (15)	0.0440 (16)	0.0049 (12)	0.0006 (13)	0.0066 (12)
Cl1	0.0435 (5)	0.0572 (6)	0.0666 (6)	−0.0003 (4)	−0.0052 (4)	0.0058 (4)
F1	0.0444 (11)	0.0784 (14)	0.0528 (12)	0.0031 (10)	−0.0082 (9)	0.0204 (10)
F2	0.0495 (12)	0.0830 (16)	0.0895 (17)	0.0280 (11)	0.0141 (11)	−0.0104 (13)
N1	0.0304 (11)	0.0443 (13)	0.0336 (12)	0.0099 (10)	0.0091 (10)	0.0111 (10)
N2	0.0423 (13)	0.0449 (14)	0.0341 (13)	0.0058 (11)	0.0096 (11)	0.0062 (11)
O3	0.0349 (11)	0.0801 (17)	0.0385 (12)	0.0114 (11)	0.0119 (9)	0.0125 (11)
S1	0.0327 (4)	0.0449 (5)	0.0426 (5)	0.0098 (3)	0.0088 (3)	0.0114 (3)

C1—F2	1.343 (4)	C7—O3	1.220 (3)
C1—C2	1.366 (4)	C7—N1	1.371 (4)
C1—C6	1.393 (4)	C8—N2	1.306 (4)
C2—C3	1.374 (5)	C8—N1	1.379 (4)
C2—H2	0.9300	C8—S1	1.729 (3)
C3—F1	1.348 (3)	C9—C10	1.334 (5)
C3—C4	1.374 (5)	C9—N2	1.378 (4)
C4—C5	1.376 (4)	C9—H9	0.9300
C4—H4	0.9300	C10—Cl1	1.719 (3)
C5—C6	1.394 (4)	C10—S1	1.730 (3)
C5—H5	0.9300	N1—H1	0.8600
C6—C7	1.480 (4)
F2—C1—C2	117.5 (3)	O3—C7—N1	120.7 (3)
F2—C1—C6	119.1 (3)	O3—C7—C6	123.3 (3)
C2—C1—C6	123.4 (3)	N1—C7—C6	116.0 (2)
C1—C2—C3	117.4 (3)	N2—C8—N1	121.3 (2)
C1—C2—H2	121.3	N2—C8—S1	115.8 (2)
C3—C2—H2	121.3	N1—C8—S1	122.9 (2)
F1—C3—C4	119.0 (3)	C10—C9—N2	115.1 (3)
F1—C3—C2	118.5 (3)	C10—C9—H9	122.5
C4—C3—C2	122.5 (3)	N2—C9—H9	122.5
C3—C4—C5	118.3 (3)	C9—C10—Cl1	127.8 (3)
C3—C4—H4	120.9	C9—C10—S1	111.6 (2)
C5—C4—H4	120.9	Cl1—C10—S1	120.56 (19)
C4—C5—C6	122.0 (3)	C7—N1—C8	122.4 (2)
C4—C5—H5	119.0	C7—N1—H1	118.8
C6—C5—H5	119.0	C8—N1—H1	118.8
C1—C6—C5	116.4 (3)	C8—N2—C9	110.0 (3)
C1—C6—C7	120.8 (3)	C8—S1—C10	87.44 (14)
C5—C6—C7	122.6 (3)
F2—C1—C2—C3	−177.5 (3)	C1—C6—C7—N1	145.0 (3)
C6—C1—C2—C3	0.2 (5)	C5—C6—C7—N1	−40.5 (4)
C1—C2—C3—F1	178.6 (3)	N2—C9—C10—Cl1	178.5 (2)
C1—C2—C3—C4	−0.3 (5)	N2—C9—C10—S1	−0.6 (4)
F1—C3—C4—C5	−179.1 (3)	O3—C7—N1—C8	−4.4 (4)
C2—C3—C4—C5	−0.1 (5)	C6—C7—N1—C8	173.7 (2)
C3—C4—C5—C6	0.8 (4)	N2—C8—N1—C7	−179.6 (3)
F2—C1—C6—C5	178.1 (3)	S1—C8—N1—C7	−0.1 (4)
C2—C1—C6—C5	0.4 (4)	N1—C8—N2—C9	179.1 (3)
F2—C1—C6—C7	−7.1 (4)	S1—C8—N2—C9	−0.4 (3)
C2—C1—C6—C7	175.2 (3)	C10—C9—N2—C8	0.7 (4)
C4—C5—C6—C1	−0.9 (4)	N2—C8—S1—C10	0.1 (2)
C4—C5—C6—C7	−175.6 (3)	N1—C8—S1—C10	−179.4 (3)
C1—C6—C7—O3	−37.0 (4)	C9—C10—S1—C8	0.3 (3)
C5—C6—C7—O3	137.5 (3)	Cl1—C10—S1—C8	−178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.86	2.15	2.988 (3)	166
C4—H4···F2ii	0.93	2.38	3.127 (4)	137
C4—H4···O3ii	0.93	2.56	3.329 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.86	2.15	2.988 (3)	166
C4—H4⋯F2ii	0.93	2.38	3.127 (4)	137
C4—H4⋯O3ii	0.93	2.56	3.329 (4)	140

Symmetry codes: (i) ; (ii) .