Crystal structure of tolyl-fluanid.

The title compound, C10H13Cl2FN2O2S2 {systematic name: N-[(di-chloro-fluoro-methyl)-sulfanyl]-N',N'-dimethyl-N-p-tolyl-sulfamide}, is a well known fungicide. The dihedral angle between the mean plane of the di-methyl-amino group and that of the benzene ring is 32.3 (3)°. One Cl atom and one F atom of the di-chloro-fluoro-methyl-thio group are disordered over two sets of sites with an occupancy ratio of 0.605 (9):0.395 (9). In the crystal structure, two C-H⋯Cl hydrogen bonds link adjacent mol-ecules, forming dimers with R 2 (2)(14) loops. C-H⋯O hydrogen bonds link pairs of dimers into chains along the b-axis direction. These chains are joined by an additional C-H⋯O contact, generating a sheet in the ab plane.

Related literature

For information on the toxicity and fungicidal properties of the title compound, see: Sargis et al. (2012 ▶); Stajnbaher & Zupancic-Kralj (2008 ▶). For a related crystal structure, see: Ogata et al. (1986 ▶).

Experimental

Crystal data

C10H13Cl2FN2O2S2

M = 347.24

Monoclinic,

a = 23.7638 (19) Å

b = 8.7046 (7) Å

c = 14.6559 (11) Å

β = 102.133 (3)°

V = 2963.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.73 mm−1

T = 173 K

0.19 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.874, T max = 0.944

18246 measured reflections

2913 independent reflections

2236 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.135

S = 1.14

2913 reflections

194 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814020741/sj5426sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814020741/sj5426Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S1600536814020741/sj5426fig1.tif

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. Only atoms of the major disorder components are shown.

Click here for additional data file.

. DOI: 10.1107/S1600536814020741/sj5426fig2.tif

Crystal packing of the title compound with C–H⋯Cl and C–H⋯O hydrogen bonds are shown as dashed lines. H atoms bonded to C atoms have been omitted for clarity, except H atoms of hydrogen bonds. Only atoms of the major disorder components are shown.

CCDC reference: 1024472

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H13Cl2FN2O2S2	F(000) = 1424
Mr = 347.24	Dx = 1.556 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6794 reflections
a = 23.7638 (19) Å	θ = 2.8–27.1°
b = 8.7046 (7) Å	µ = 0.73 mm−1
c = 14.6559 (11) Å	T = 173 K
β = 102.133 (3)°	Block, colourless
V = 2963.9 (4) Å3	0.19 × 0.10 × 0.08 mm
Z = 8

Bruker APEXII CCD diffractometer	2913 independent reflections
Radiation source: fine-focus sealed tube	2236 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
φ and ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −29→26
Tmin = 0.874, Tmax = 0.944	k = −10→10
18246 measured reflections	l = −18→18

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0259P)2 + 15.3569P] where P = (Fo2 + 2Fc2)/3
2913 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.50 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	Occ. (<1)
Cl1	0.42965 (16)	0.2602 (5)	0.1267 (3)	0.0592 (11)	0.605 (9)
Cl1'	0.3886 (3)	0.4591 (10)	0.1620 (5)	0.0549 (18)	0.395 (9)
Cl2	0.32595 (6)	0.33538 (16)	−0.00564 (8)	0.0545 (4)
S1	0.33566 (4)	0.30575 (13)	0.35656 (7)	0.0302 (3)
S2	0.31078 (4)	0.20191 (13)	0.16220 (7)	0.0307 (3)
F1	0.3625 (4)	0.4708 (12)	0.1530 (7)	0.052 (2)	0.605 (9)
F1'	0.4106 (7)	0.1951 (19)	0.1104 (9)	0.066 (4)	0.395 (9)
O1	0.38994 (13)	0.3659 (4)	0.4004 (2)	0.0438 (8)
O2	0.29116 (13)	0.4060 (4)	0.31161 (19)	0.0402 (8)
N1	0.34588 (14)	0.1819 (4)	0.2728 (2)	0.0304 (8)
N2	0.31214 (16)	0.2043 (4)	0.4323 (2)	0.0376 (9)
C1	0.4891 (2)	−0.3490 (7)	0.3831 (4)	0.0685 (17)
H1A	0.5214	−0.3487	0.3510	0.103*
H1B	0.4661	−0.4421	0.3663	0.103*
H1C	0.5040	−0.3467	0.4507	0.103*
C2	0.4519 (2)	−0.2090 (6)	0.3541 (3)	0.0428 (11)
C3	0.39365 (19)	−0.2240 (6)	0.3152 (3)	0.0385 (11)
H3	0.3771	−0.3236	0.3064	0.046*
C4	0.35902 (18)	−0.0958 (5)	0.2887 (3)	0.0334 (10)
H4	0.3192	−0.1084	0.2623	0.040*
C5	0.38234 (17)	0.0485 (5)	0.3007 (3)	0.0308 (9)
C6	0.4402 (2)	0.0684 (6)	0.3386 (4)	0.0474 (12)
H6	0.4565	0.1684	0.3458	0.057*
C7	0.4738 (2)	−0.0593 (6)	0.3658 (4)	0.0585 (15)
H7	0.5133	−0.0452	0.3937	0.070*
C8	0.2585 (2)	0.1181 (6)	0.3994 (4)	0.0546 (14)
H8A	0.2674	0.0187	0.3743	0.082*
H8B	0.2331	0.1768	0.3503	0.082*
H8C	0.2393	0.1014	0.4515	0.082*
C9	0.3532 (3)	0.1351 (7)	0.5110 (3)	0.0612 (16)
H9A	0.3347	0.1233	0.5644	0.092*
H9B	0.3870	0.2018	0.5285	0.092*
H9C	0.3652	0.0341	0.4925	0.092*
C10	0.3611 (2)	0.3152 (6)	0.1127 (3)	0.0458 (12)

	U11	U22	U33	U12	U13	U23
Cl1	0.0428 (17)	0.057 (2)	0.084 (2)	−0.0029 (13)	0.0277 (15)	0.0112 (17)
Cl1'	0.070 (4)	0.052 (3)	0.048 (2)	−0.015 (3)	0.025 (3)	−0.0026 (19)
Cl2	0.0701 (9)	0.0687 (9)	0.0275 (6)	0.0036 (7)	0.0163 (6)	0.0102 (6)
S1	0.0345 (6)	0.0318 (6)	0.0237 (5)	−0.0008 (5)	0.0050 (4)	−0.0004 (4)
S2	0.0316 (6)	0.0378 (6)	0.0221 (5)	0.0014 (5)	0.0044 (4)	0.0015 (4)
F1	0.065 (5)	0.038 (4)	0.056 (4)	−0.010 (5)	0.025 (5)	−0.009 (3)
F1'	0.066 (8)	0.079 (10)	0.066 (7)	0.057 (7)	0.047 (7)	0.028 (7)
O1	0.0412 (19)	0.044 (2)	0.0430 (18)	−0.0107 (15)	0.0016 (14)	−0.0031 (15)
O2	0.0482 (19)	0.0385 (19)	0.0328 (16)	0.0149 (15)	0.0062 (14)	−0.0027 (14)
N1	0.0344 (19)	0.036 (2)	0.0203 (16)	0.0061 (16)	0.0038 (14)	−0.0011 (15)
N2	0.050 (2)	0.040 (2)	0.0251 (17)	−0.0075 (18)	0.0119 (16)	−0.0017 (16)
C1	0.058 (4)	0.050 (4)	0.091 (4)	0.011 (3)	−0.001 (3)	0.024 (3)
C2	0.041 (3)	0.043 (3)	0.045 (3)	0.003 (2)	0.010 (2)	0.009 (2)
C3	0.044 (3)	0.038 (3)	0.035 (2)	−0.001 (2)	0.010 (2)	0.000 (2)
C4	0.029 (2)	0.043 (3)	0.027 (2)	0.0004 (19)	0.0039 (17)	−0.0059 (19)
C5	0.032 (2)	0.036 (3)	0.025 (2)	0.0080 (19)	0.0069 (17)	0.0035 (18)
C6	0.034 (3)	0.035 (3)	0.069 (3)	−0.004 (2)	0.003 (2)	0.010 (2)
C7	0.034 (3)	0.050 (3)	0.083 (4)	0.000 (2)	−0.007 (3)	0.014 (3)
C8	0.061 (3)	0.052 (3)	0.062 (3)	−0.019 (3)	0.038 (3)	−0.013 (3)
C9	0.089 (4)	0.060 (4)	0.033 (3)	0.007 (3)	0.010 (3)	0.019 (3)
C10	0.044 (3)	0.062 (4)	0.033 (2)	−0.002 (2)	0.011 (2)	0.010 (2)

Cl1—C10	1.670 (6)	C1—H1C	0.9800
Cl1'—C10	1.523 (10)	C2—C3	1.389 (6)
Cl2—C10	1.768 (5)	C2—C7	1.400 (7)
S1—O1	1.415 (3)	C3—C4	1.392 (6)
S1—O2	1.422 (3)	C3—H3	0.9500
S1—N2	1.608 (3)	C4—C5	1.369 (6)
S1—N1	1.690 (3)	C4—H4	0.9500
S2—N1	1.669 (3)	C5—C6	1.381 (6)
S2—C10	1.814 (5)	C6—C7	1.378 (7)
F1—C10	1.474 (12)	C6—H6	0.9500
F1'—C10	1.581 (11)	C7—H7	0.9500
N1—C5	1.455 (5)	C8—H8A	0.9800
N2—C8	1.470 (6)	C8—H8B	0.9800
N2—C9	1.473 (6)	C8—H8C	0.9800
C1—C2	1.513 (7)	C9—H9A	0.9800
C1—H1A	0.9800	C9—H9B	0.9800
C1—H1B	0.9800	C9—H9C	0.9800
O1—S1—O2	120.1 (2)	C7—C6—H6	120.6
O1—S1—N2	107.78 (19)	C5—C6—H6	120.6
O2—S1—N2	108.94 (19)	C6—C7—C2	122.5 (5)
O1—S1—N1	108.03 (18)	C6—C7—H7	118.8
O2—S1—N1	105.17 (17)	C2—C7—H7	118.8
N2—S1—N1	105.96 (18)	N2—C8—H8A	109.5
N1—S2—C10	102.03 (19)	N2—C8—H8B	109.5
C5—N1—S2	120.2 (3)	H8A—C8—H8B	109.5
C5—N1—S1	118.3 (2)	N2—C8—H8C	109.5
S2—N1—S1	121.3 (2)	H8A—C8—H8C	109.5
C8—N2—C9	115.7 (4)	H8B—C8—H8C	109.5
C8—N2—S1	117.2 (3)	N2—C9—H9A	109.5
C9—N2—S1	119.7 (3)	N2—C9—H9B	109.5
C2—C1—H1A	109.5	H9A—C9—H9B	109.5
C2—C1—H1B	109.5	N2—C9—H9C	109.5
H1A—C1—H1B	109.5	H9A—C9—H9C	109.5
C2—C1—H1C	109.5	H9B—C9—H9C	109.5
H1A—C1—H1C	109.5	F1—C10—Cl1'	23.6 (3)
H1B—C1—H1C	109.5	F1—C10—F1'	131.4 (7)
C3—C2—C7	116.8 (4)	Cl1'—C10—F1'	107.8 (7)
C3—C2—C1	120.9 (5)	F1—C10—Cl1	106.0 (5)
C7—C2—C1	122.4 (4)	Cl1'—C10—Cl1	82.3 (4)
C2—C3—C4	121.3 (4)	F1'—C10—Cl1	25.9 (7)
C2—C3—H3	119.4	F1—C10—Cl2	105.5 (5)
C4—C3—H3	119.4	Cl1'—C10—Cl2	116.8 (4)
C5—C4—C3	120.0 (4)	F1'—C10—Cl2	104.1 (6)
C5—C4—H4	120.0	Cl1—C10—Cl2	113.3 (3)
C3—C4—H4	120.0	F1—C10—S2	107.5 (5)
C4—C5—C6	120.6 (4)	Cl1'—C10—S2	120.7 (4)
C4—C5—N1	119.7 (4)	F1'—C10—S2	101.9 (7)
C6—C5—N1	119.8 (4)	Cl1—C10—S2	120.2 (3)
C7—C6—C5	118.9 (4)	Cl2—C10—S2	103.4 (2)
C10—S2—N1—C5	−92.6 (3)	C3—C4—C5—C6	0.2 (6)
C10—S2—N1—S1	92.9 (3)	C3—C4—C5—N1	180.0 (4)
O1—S1—N1—C5	60.6 (3)	S2—N1—C5—C4	−59.3 (5)
O2—S1—N1—C5	−170.0 (3)	S1—N1—C5—C4	115.4 (4)
N2—S1—N1—C5	−54.7 (3)	S2—N1—C5—C6	120.5 (4)
O1—S1—N1—S2	−124.8 (2)	S1—N1—C5—C6	−64.9 (5)
O2—S1—N1—S2	4.6 (3)	C4—C5—C6—C7	−1.2 (7)
N2—S1—N1—S2	119.9 (2)	N1—C5—C6—C7	179.0 (4)
O1—S1—N2—C8	−174.3 (3)	C5—C6—C7—C2	1.9 (8)
O2—S1—N2—C8	53.9 (4)	C3—C2—C7—C6	−1.5 (8)
N1—S1—N2—C8	−58.8 (4)	C1—C2—C7—C6	179.3 (5)
O1—S1—N2—C9	−25.5 (4)	N1—S2—C10—F1	−69.9 (5)
O2—S1—N2—C9	−157.4 (4)	N1—S2—C10—Cl1'	−48.4 (5)
N1—S1—N2—C9	89.9 (4)	N1—S2—C10—F1'	70.9 (7)
C7—C2—C3—C4	0.4 (7)	N1—S2—C10—Cl1	51.2 (4)
C1—C2—C3—C4	179.7 (5)	N1—S2—C10—Cl2	178.7 (2)
C2—C3—C4—C5	0.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1i	0.98	2.59	3.469 (7)	150
C6—H6···Cl1ii	0.95	2.77	3.457 (6)	130
C4—H4···O2iii	0.95	2.62	3.563 (5)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1i	0.98	2.59	3.469 (7)	150
C6—H6⋯Cl1ii	0.95	2.77	3.457 (6)	130
C4—H4⋯O2iii	0.95	2.62	3.563 (5)	171

Symmetry codes: (i) ; (ii) ; (iii) .