Crystal structure of cafenstrole.

The title compound (systematic name: N,N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide), C16H22N4O3S, is a triazole herbicide. The dihedral angle between the planes of the triazole and benzene ring planes is 88.14 (10)°. In the crystal, C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions link adjacent mol-ecules, forming one-dimensional chains along the a axis.

Related literature

For information on the herbicidal properties of the title compound, see: Takahashi et al. (2001 ▸). For related crystal structure, see: Ohkata et al. (2002 ▸).

Experimental

Crystal data

C16H22N4O3S

M = 350.43

Monoclinic,

a = 7.2800 (3) Å

b = 8.0410 (4) Å

c = 30.1792 (13) Å

β = 95.290 (3)°

V = 1759.12 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.36 × 0.30 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.929, T max = 0.996

11871 measured reflections

3385 independent reflections

2760 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.118

S = 1.12

3385 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015013869/hg5453sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013869/hg5453Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015013869/hg5453Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015013869/hg5453fig1.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.

Click here for additional data file.

b . DOI: 10.1107/S2056989015013869/hg5453fig2.tif

Crystal packing viewed along the b axis. The inter­molecular inter­actions are shown as dashed lines.

CCDC reference: 1414616

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

C16H22N4O3S	Dx = 1.323 Mg m−3
Mr = 350.43	Melting point: 390 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.2800 (3) Å	Cell parameters from 3608 reflections
b = 8.0410 (4) Å	θ = 2.6–25.8°
c = 30.1792 (13) Å	µ = 0.21 mm−1
β = 95.290 (3)°	T = 173 K
V = 1759.12 (14) Å3	Plate, colourless
Z = 4	0.36 × 0.30 × 0.02 mm
F(000) = 744

Bruker APEXII CCD diffractometer	2760 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.033
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 26.0°, θmin = 1.4°
Tmin = 0.929, Tmax = 0.996	h = −8→7
11871 measured reflections	k = −9→9
3385 independent reflections	l = −37→37

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0373P)2 + 1.5378P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
3385 reflections	Δρmax = 0.32 e Å−3
222 parameters	Δρmin = −0.35 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.

	x	y	z	Uiso*/Ueq
S1	0.41370 (9)	0.41398 (9)	0.10060 (2)	0.03098 (19)
O1	0.3991 (3)	0.2440 (2)	0.08694 (6)	0.0440 (5)
O2	0.5862 (2)	0.4698 (3)	0.12191 (6)	0.0426 (5)
O3	−0.0331 (3)	0.6067 (3)	0.24940 (6)	0.0450 (5)
N1	0.0629 (3)	0.4287 (3)	0.12755 (6)	0.0321 (5)
N2	0.2960 (3)	0.4724 (3)	0.18146 (6)	0.0280 (5)
N3	0.1290 (3)	0.4783 (3)	0.19847 (6)	0.0262 (5)
N4	0.2305 (3)	0.4731 (3)	0.27538 (6)	0.0265 (5)
C1	0.3372 (3)	0.5499 (3)	0.05661 (7)	0.0243 (5)
C2	0.2701 (3)	0.4890 (3)	0.01447 (7)	0.0250 (5)
C3	0.2198 (3)	0.6048 (3)	−0.01847 (7)	0.0262 (5)
H3	0.1760	0.5657	−0.0472	0.031*
C4	0.2303 (3)	0.7740 (3)	−0.01148 (8)	0.0275 (6)
C5	0.2917 (3)	0.8308 (3)	0.03064 (8)	0.0293 (6)
H5	0.2964	0.9472	0.0360	0.035*
C6	0.3468 (3)	0.7227 (3)	0.06518 (7)	0.0272 (6)
C7	0.2494 (4)	0.3081 (3)	0.00170 (8)	0.0348 (6)
H7A	0.1922	0.2994	−0.0289	0.052*
H7B	0.1713	0.2521	0.0219	0.052*
H7C	0.3711	0.2552	0.0038	0.052*
C8	0.1789 (4)	0.8928 (4)	−0.04883 (8)	0.0389 (7)
H8A	0.2902	0.9482	−0.0574	0.058*
H8B	0.0931	0.9763	−0.0391	0.058*
H8C	0.1199	0.8317	−0.0744	0.058*
C9	0.4143 (4)	0.7991 (4)	0.10936 (8)	0.0456 (8)
H9A	0.5462	0.7758	0.1159	0.068*
H9B	0.3459	0.7514	0.1328	0.068*
H9C	0.3947	0.9196	0.1081	0.068*
C10	0.2465 (3)	0.4418 (3)	0.13928 (7)	0.0263 (5)
C11	−0.0062 (3)	0.4550 (3)	0.16559 (8)	0.0302 (6)
H11	−0.1343	0.4573	0.1694	0.036*
C12	0.1025 (3)	0.5235 (3)	0.24394 (8)	0.0293 (6)
C13	0.3683 (3)	0.3424 (3)	0.27089 (8)	0.0253 (5)
H13A	0.3367	0.2817	0.2427	0.030*
H13B	0.3635	0.2621	0.2956	0.030*
C14	0.5623 (3)	0.4096 (4)	0.27125 (9)	0.0364 (6)
H14A	0.5731	0.4752	0.2443	0.055*
H14B	0.6499	0.3169	0.2723	0.055*
H14C	0.5896	0.4803	0.2975	0.055*
C15	0.2014 (4)	0.5244 (4)	0.32107 (8)	0.0371 (7)
H15A	0.1512	0.6389	0.3205	0.045*
H15B	0.3214	0.5253	0.3394	0.045*
C16	0.0700 (4)	0.4095 (5)	0.34227 (9)	0.0528 (9)
H16A	−0.0498	0.4096	0.3245	0.079*
H16B	0.0542	0.4480	0.3725	0.079*
H16C	0.1204	0.2964	0.3435	0.079*

	U11	U22	U33	U12	U13	U23
S1	0.0289 (4)	0.0379 (4)	0.0261 (3)	0.0080 (3)	0.0024 (2)	0.0056 (3)
O1	0.0604 (13)	0.0328 (11)	0.0394 (10)	0.0158 (10)	0.0082 (9)	0.0063 (9)
O2	0.0237 (10)	0.0704 (15)	0.0327 (9)	0.0075 (10)	−0.0024 (7)	0.0098 (10)
O3	0.0377 (11)	0.0587 (14)	0.0388 (10)	0.0233 (10)	0.0043 (8)	0.0019 (10)
N1	0.0265 (11)	0.0399 (14)	0.0290 (10)	−0.0012 (10)	−0.0020 (9)	0.0017 (10)
N2	0.0220 (11)	0.0345 (12)	0.0275 (10)	0.0021 (9)	0.0020 (8)	0.0046 (10)
N3	0.0213 (11)	0.0306 (12)	0.0264 (10)	0.0019 (9)	0.0000 (8)	0.0035 (9)
N4	0.0290 (11)	0.0244 (11)	0.0251 (10)	0.0033 (9)	−0.0031 (8)	−0.0011 (9)
C1	0.0214 (12)	0.0284 (13)	0.0230 (11)	0.0013 (11)	0.0018 (9)	0.0029 (11)
C2	0.0173 (12)	0.0319 (14)	0.0261 (11)	−0.0003 (10)	0.0037 (9)	−0.0022 (11)
C3	0.0241 (12)	0.0326 (14)	0.0215 (11)	0.0007 (11)	0.0003 (9)	−0.0030 (11)
C4	0.0233 (13)	0.0316 (14)	0.0276 (12)	0.0018 (11)	0.0026 (10)	0.0034 (11)
C5	0.0321 (14)	0.0252 (13)	0.0309 (12)	−0.0004 (11)	0.0043 (11)	−0.0005 (11)
C6	0.0272 (13)	0.0318 (14)	0.0226 (11)	−0.0017 (11)	0.0016 (10)	−0.0004 (11)
C7	0.0390 (16)	0.0295 (15)	0.0353 (13)	0.0013 (13)	0.0002 (11)	−0.0050 (12)
C8	0.0479 (17)	0.0350 (16)	0.0328 (13)	0.0050 (14)	−0.0023 (12)	0.0057 (13)
C9	0.066 (2)	0.0384 (17)	0.0306 (14)	−0.0064 (16)	−0.0051 (13)	−0.0052 (13)
C10	0.0267 (13)	0.0270 (13)	0.0246 (11)	0.0018 (11)	−0.0011 (10)	0.0046 (11)
C11	0.0256 (13)	0.0338 (15)	0.0299 (12)	0.0007 (11)	−0.0034 (10)	0.0067 (12)
C12	0.0253 (14)	0.0319 (14)	0.0306 (13)	0.0029 (12)	0.0022 (10)	0.0014 (11)
C13	0.0276 (13)	0.0210 (12)	0.0265 (11)	0.0040 (10)	−0.0014 (10)	0.0047 (10)
C14	0.0278 (14)	0.0360 (15)	0.0441 (15)	−0.0003 (12)	−0.0026 (11)	0.0088 (13)
C15	0.0461 (17)	0.0354 (15)	0.0281 (13)	0.0066 (13)	−0.0057 (12)	−0.0099 (12)
C16	0.0481 (18)	0.083 (3)	0.0285 (13)	−0.0110 (18)	0.0087 (13)	−0.0122 (16)

S1—O1	1.429 (2)	C6—C9	1.509 (3)
S1—O2	1.4293 (19)	C7—H7A	0.9800
S1—C1	1.769 (2)	C7—H7B	0.9800
S1—C10	1.777 (2)	C7—H7C	0.9800
O3—C12	1.216 (3)	C8—H8A	0.9800
N1—C11	1.313 (3)	C8—H8B	0.9800
N1—C10	1.355 (3)	C8—H8C	0.9800
N2—C10	1.314 (3)	C9—H9A	0.9800
N2—N3	1.364 (3)	C9—H9B	0.9800
N3—C11	1.345 (3)	C9—H9C	0.9800
N3—C12	1.450 (3)	C11—H11	0.9500
N4—C12	1.331 (3)	C13—C14	1.511 (3)
N4—C13	1.468 (3)	C13—H13A	0.9900
N4—C15	1.473 (3)	C13—H13B	0.9900
C1—C2	1.408 (3)	C14—H14A	0.9800
C1—C6	1.414 (4)	C14—H14B	0.9800
C2—C3	1.387 (3)	C14—H14C	0.9800
C2—C7	1.509 (3)	C15—C16	1.513 (4)
C3—C4	1.378 (4)	C15—H15A	0.9900
C3—H3	0.9500	C15—H15B	0.9900
C4—C5	1.385 (3)	C16—H16A	0.9800
C4—C8	1.499 (3)	C16—H16B	0.9800
C5—C6	1.387 (3)	C16—H16C	0.9800
C5—H5	0.9500
O1—S1—O2	118.01 (13)	H8A—C8—H8C	109.5
O1—S1—C1	111.37 (11)	H8B—C8—H8C	109.5
O2—S1—C1	110.25 (12)	C6—C9—H9A	109.5
O1—S1—C10	105.83 (12)	C6—C9—H9B	109.5
O2—S1—C10	106.94 (11)	H9A—C9—H9B	109.5
C1—S1—C10	103.17 (11)	C6—C9—H9C	109.5
C11—N1—C10	101.98 (19)	H9A—C9—H9C	109.5
C10—N2—N3	101.33 (18)	H9B—C9—H9C	109.5
C11—N3—N2	109.55 (19)	N2—C10—N1	116.4 (2)
C11—N3—C12	125.5 (2)	N2—C10—S1	121.10 (18)
N2—N3—C12	124.48 (19)	N1—C10—S1	122.51 (17)
C12—N4—C13	126.3 (2)	N1—C11—N3	110.7 (2)
C12—N4—C15	115.5 (2)	N1—C11—H11	124.6
C13—N4—C15	116.46 (19)	N3—C11—H11	124.6
C2—C1—C6	120.9 (2)	O3—C12—N4	126.5 (2)
C2—C1—S1	121.47 (19)	O3—C12—N3	116.5 (2)
C6—C1—S1	117.58 (17)	N4—C12—N3	116.9 (2)
C3—C2—C1	117.4 (2)	N4—C13—C14	112.9 (2)
C3—C2—C7	116.8 (2)	N4—C13—H13A	109.0
C1—C2—C7	125.8 (2)	C14—C13—H13A	109.0
C4—C3—C2	123.1 (2)	N4—C13—H13B	109.0
C4—C3—H3	118.4	C14—C13—H13B	109.0
C2—C3—H3	118.4	H13A—C13—H13B	107.8
C3—C4—C5	118.3 (2)	C13—C14—H14A	109.5
C3—C4—C8	120.5 (2)	C13—C14—H14B	109.5
C5—C4—C8	121.1 (2)	H14A—C14—H14B	109.5
C4—C5—C6	122.0 (2)	C13—C14—H14C	109.5
C4—C5—H5	119.0	H14A—C14—H14C	109.5
C6—C5—H5	119.0	H14B—C14—H14C	109.5
C5—C6—C1	118.2 (2)	N4—C15—C16	112.1 (2)
C5—C6—C9	117.2 (2)	N4—C15—H15A	109.2
C1—C6—C9	124.6 (2)	C16—C15—H15A	109.2
C2—C7—H7A	109.5	N4—C15—H15B	109.2
C2—C7—H7B	109.5	C16—C15—H15B	109.2
H7A—C7—H7B	109.5	H15A—C15—H15B	107.9
C2—C7—H7C	109.5	C15—C16—H16A	109.5
H7A—C7—H7C	109.5	C15—C16—H16B	109.5
H7B—C7—H7C	109.5	H16A—C16—H16B	109.5
C4—C8—H8A	109.5	C15—C16—H16C	109.5
C4—C8—H8B	109.5	H16A—C16—H16C	109.5
H8A—C8—H8B	109.5	H16B—C16—H16C	109.5
C4—C8—H8C	109.5
C10—N2—N3—C11	−1.4 (3)	N3—N2—C10—S1	−177.87 (17)
C10—N2—N3—C12	−174.3 (2)	C11—N1—C10—N2	0.7 (3)
O1—S1—C1—C2	0.7 (2)	C11—N1—C10—S1	178.95 (19)
O2—S1—C1—C2	133.7 (2)	O1—S1—C10—N2	113.2 (2)
C10—S1—C1—C2	−112.4 (2)	O2—S1—C10—N2	−13.4 (2)
O1—S1—C1—C6	−178.97 (18)	C1—S1—C10—N2	−129.7 (2)
O2—S1—C1—C6	−46.0 (2)	O1—S1—C10—N1	−65.0 (2)
C10—S1—C1—C6	67.9 (2)	O2—S1—C10—N1	168.3 (2)
C6—C1—C2—C3	2.1 (3)	C1—S1—C10—N1	52.1 (2)
S1—C1—C2—C3	−177.58 (17)	C10—N1—C11—N3	−1.5 (3)
C6—C1—C2—C7	−178.5 (2)	N2—N3—C11—N1	2.0 (3)
S1—C1—C2—C7	1.8 (3)	C12—N3—C11—N1	174.8 (2)
C1—C2—C3—C4	−1.0 (4)	C13—N4—C12—O3	164.5 (3)
C7—C2—C3—C4	179.6 (2)	C15—N4—C12—O3	0.2 (4)
C2—C3—C4—C5	−0.9 (4)	C13—N4—C12—N3	−17.0 (4)
C2—C3—C4—C8	178.2 (2)	C15—N4—C12—N3	178.7 (2)
C3—C4—C5—C6	1.7 (4)	C11—N3—C12—O3	−29.9 (4)
C8—C4—C5—C6	−177.4 (2)	N2—N3—C12—O3	141.9 (3)
C4—C5—C6—C1	−0.6 (4)	C11—N3—C12—N4	151.5 (2)
C4—C5—C6—C9	178.9 (2)	N2—N3—C12—N4	−36.8 (3)
C2—C1—C6—C5	−1.3 (4)	C12—N4—C13—C14	110.4 (3)
S1—C1—C6—C5	178.35 (18)	C15—N4—C13—C14	−85.5 (3)
C2—C1—C6—C9	179.2 (2)	C12—N4—C15—C16	82.9 (3)
S1—C1—C6—C9	−1.2 (3)	C13—N4—C15—C16	−83.0 (3)
N3—N2—C10—N1	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2i	0.95	2.38	3.136 (3)	136
C7—H7C···Cg1ii	0.98	2.80	3.561 (3)	135

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C11H11O2i	0.95	2.38	3.136(3)	136
C7H7C Cg1ii	0.98	2.80	3.561(3)	135

Symmetry codes: (i) ; (ii) .