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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 8| August 2015| Page o614
https://doi.org/10.1107/S2056989015013869

Crystal structure of cafenstrole

Gihaeng Kang,a Jineun Kim,a* Hyunjin Parka and Tae Ho Kima*

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr

Edited by P. C. Healy, Griffith University, Australia (Received 14 July 2015; accepted 22 July 2015; online 29 July 2015)

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 inter­actions link adjacent mol­ecules, forming one-dimensional chains along the a axis.

CCDC reference: 1414616

Similar articles

1. Related literature

For information on the herbicidal properties of the title compound, see: Takahashi et al. (2001[Takahashi, H., Ohki, A., Kanzaki, M., Tanaka, A., Sato, Y., Matthes, B., Böger, P. & Wakabayashi, K. (2001). J. Biosci. 56, 781-786.]). For related crystal structure, see: Ohkata et al. (2002[Ohkata, K., Yano, T., Kojima, S., Hiraga, Y., Yoshii, T. & Hori, M. (2002). Bull. Chem. Soc. Jpn, 75, 567-574.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C16H22N4O3S

  • Mr = 350.43

  • Monoclinic, P 21 /c

  • 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

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.929, Tmax = 0.996

  • 11871 measured reflections

  • 3385 independent reflections

  • 2760 reflections with I > 2σ(I)

  • Rint = 0.033

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 1414616

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015013869/hg5453sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013869/hg5453Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015013869/hg5453Isup3.cml

checkCIF report


Comment top

Cafenstrole, or N,N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide, is a triazole herbicide and has been used for rice cultivation which especially inhibits the germination of grass weeds (Takahashi et al., 2001). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), the dihedral angle between the planes of the triazole ring and the phenyl ring planes is 88.14 (10)°. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structure (Ohkata et al., 2002).

In the crystal structure (Fig. 2, Table 1), C11—H11···O2 hydrogen bonds and weak intermolecular C7—H7C···Cg1 (Cg1 is the centroid of the C1–C6 ring) interactions link adjacent molecules, forming one-dimensional chains along to a-axis.

Related literature top

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 top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH3CN gave single crystals suitable for X-ray analysis.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for methyl group, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for Csp3—H, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.

Structure description top

Cafenstrole, or N,N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide, is a triazole herbicide and has been used for rice cultivation which especially inhibits the germination of grass weeds (Takahashi et al., 2001). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), the dihedral angle between the planes of the triazole ring and the phenyl ring planes is 88.14 (10)°. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structure (Ohkata et al., 2002).

In the crystal structure (Fig. 2, Table 1), C11—H11···O2 hydrogen bonds and weak intermolecular C7—H7C···Cg1 (Cg1 is the centroid of the C1–C6 ring) interactions link adjacent molecules, forming one-dimensional chains along to a-axis.

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

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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).

Figures top
[Figure 1] Fig. 1. 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.
[Figure 2] Fig. 2. Crystal packing viewed along the b axis. The intermolecular interactions are shown as dashed lines.
N,N-Diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide top
Crystal data top
C16H22N4O3SDx = 1.323 Mg m−3
Mr = 350.43Melting point: 390 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.2800 (3) ÅCell parameters from 3608 reflections
b = 8.0410 (4) Åθ = 2.6–25.8°
c = 30.1792 (13) ŵ = 0.21 mm−1
β = 95.290 (3)°T = 173 K
V = 1759.12 (14) Å3Plate, colourless
Z = 40.36 × 0.30 × 0.02 mm
F(000) = 744
Data collection top
Bruker APEXII CCD
diffractometer		2760 reflections with I > 2σ(I)
φ and ω scansRint = 0.033
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		θmax = 26.0°, θmin = 1.4°
Tmin = 0.929, Tmax = 0.996h = −8→7
11871 measured reflectionsk = −9→9
3385 independent reflectionsl = −37→37
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-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 reflectionsΔρmax = 0.32 e Å−3
222 parametersΔρmin = −0.35 e Å−3
Crystal data top
C16H22N4O3SV = 1759.12 (14) Å3
Mr = 350.43Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.2800 (3) ŵ = 0.21 mm−1
b = 8.0410 (4) ÅT = 173 K
c = 30.1792 (13) Å0.36 × 0.30 × 0.02 mm
β = 95.290 (3)°
Data collection top
Bruker APEXII CCD
diffractometer		3385 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		2760 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 0.996Rint = 0.033
11871 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.12Δρmax = 0.32 e Å−3
3385 reflectionsΔρmin = −0.35 e Å−3
222 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.41370 (9)0.41398 (9)0.10060 (2)0.03098 (19)
O10.3991 (3)0.2440 (2)0.08694 (6)0.0440 (5)
O20.5862 (2)0.4698 (3)0.12191 (6)0.0426 (5)
O3−0.0331 (3)0.6067 (3)0.24940 (6)0.0450 (5)
N10.0629 (3)0.4287 (3)0.12755 (6)0.0321 (5)
N20.2960 (3)0.4724 (3)0.18146 (6)0.0280 (5)
N30.1290 (3)0.4783 (3)0.19847 (6)0.0262 (5)
N40.2305 (3)0.4731 (3)0.27538 (6)0.0265 (5)
C10.3372 (3)0.5499 (3)0.05661 (7)0.0243 (5)
C20.2701 (3)0.4890 (3)0.01447 (7)0.0250 (5)
C30.2198 (3)0.6048 (3)−0.01847 (7)0.0262 (5)
H30.17600.5657−0.04720.031*
C40.2303 (3)0.7740 (3)−0.01148 (8)0.0275 (6)
C50.2917 (3)0.8308 (3)0.03064 (8)0.0293 (6)
H50.29640.94720.03600.035*
C60.3468 (3)0.7227 (3)0.06518 (7)0.0272 (6)
C70.2494 (4)0.3081 (3)0.00170 (8)0.0348 (6)
H7A0.19220.2994−0.02890.052*
H7B0.17130.25210.02190.052*
H7C0.37110.25520.00380.052*
C80.1789 (4)0.8928 (4)−0.04883 (8)0.0389 (7)
H8A0.29020.9482−0.05740.058*
H8B0.09310.9763−0.03910.058*
H8C0.11990.8317−0.07440.058*
C90.4143 (4)0.7991 (4)0.10936 (8)0.0456 (8)
H9A0.54620.77580.11590.068*
H9B0.34590.75140.13280.068*
H9C0.39470.91960.10810.068*
C100.2465 (3)0.4418 (3)0.13928 (7)0.0263 (5)
C11−0.0062 (3)0.4550 (3)0.16559 (8)0.0302 (6)
H11−0.13430.45730.16940.036*
C120.1025 (3)0.5235 (3)0.24394 (8)0.0293 (6)
C130.3683 (3)0.3424 (3)0.27089 (8)0.0253 (5)
H13A0.33670.28170.24270.030*
H13B0.36350.26210.29560.030*
C140.5623 (3)0.4096 (4)0.27125 (9)0.0364 (6)
H14A0.57310.47520.24430.055*
H14B0.64990.31690.27230.055*
H14C0.58960.48030.29750.055*
C150.2014 (4)0.5244 (4)0.32107 (8)0.0371 (7)
H15A0.15120.63890.32050.045*
H15B0.32140.52530.33940.045*
C160.0700 (4)0.4095 (5)0.34227 (9)0.0528 (9)
H16A−0.04980.40960.32450.079*
H16B0.05420.44800.37250.079*
H16C0.12040.29640.34350.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0289 (4)0.0379 (4)0.0261 (3)0.0080 (3)0.0024 (2)0.0056 (3)
O10.0604 (13)0.0328 (11)0.0394 (10)0.0158 (10)0.0082 (9)0.0063 (9)
O20.0237 (10)0.0704 (15)0.0327 (9)0.0075 (10)−0.0024 (7)0.0098 (10)
O30.0377 (11)0.0587 (14)0.0388 (10)0.0233 (10)0.0043 (8)0.0019 (10)
N10.0265 (11)0.0399 (14)0.0290 (10)−0.0012 (10)−0.0020 (9)0.0017 (10)
N20.0220 (11)0.0345 (12)0.0275 (10)0.0021 (9)0.0020 (8)0.0046 (10)
N30.0213 (11)0.0306 (12)0.0264 (10)0.0019 (9)0.0000 (8)0.0035 (9)
N40.0290 (11)0.0244 (11)0.0251 (10)0.0033 (9)−0.0031 (8)−0.0011 (9)
C10.0214 (12)0.0284 (13)0.0230 (11)0.0013 (11)0.0018 (9)0.0029 (11)
C20.0173 (12)0.0319 (14)0.0261 (11)−0.0003 (10)0.0037 (9)−0.0022 (11)
C30.0241 (12)0.0326 (14)0.0215 (11)0.0007 (11)0.0003 (9)−0.0030 (11)
C40.0233 (13)0.0316 (14)0.0276 (12)0.0018 (11)0.0026 (10)0.0034 (11)
C50.0321 (14)0.0252 (13)0.0309 (12)−0.0004 (11)0.0043 (11)−0.0005 (11)
C60.0272 (13)0.0318 (14)0.0226 (11)−0.0017 (11)0.0016 (10)−0.0004 (11)
C70.0390 (16)0.0295 (15)0.0353 (13)0.0013 (13)0.0002 (11)−0.0050 (12)
C80.0479 (17)0.0350 (16)0.0328 (13)0.0050 (14)−0.0023 (12)0.0057 (13)
C90.066 (2)0.0384 (17)0.0306 (14)−0.0064 (16)−0.0051 (13)−0.0052 (13)
C100.0267 (13)0.0270 (13)0.0246 (11)0.0018 (11)−0.0011 (10)0.0046 (11)
C110.0256 (13)0.0338 (15)0.0299 (12)0.0007 (11)−0.0034 (10)0.0067 (12)
C120.0253 (14)0.0319 (14)0.0306 (13)0.0029 (12)0.0022 (10)0.0014 (11)
C130.0276 (13)0.0210 (12)0.0265 (11)0.0040 (10)−0.0014 (10)0.0047 (10)
C140.0278 (14)0.0360 (15)0.0441 (15)−0.0003 (12)−0.0026 (11)0.0088 (13)
C150.0461 (17)0.0354 (15)0.0281 (13)0.0066 (13)−0.0057 (12)−0.0099 (12)
C160.0481 (18)0.083 (3)0.0285 (13)−0.0110 (18)0.0087 (13)−0.0122 (16)
Geometric parameters (Å, º) top
S1—O11.429 (2)C6—C91.509 (3)
S1—O21.4293 (19)C7—H7A0.9800
S1—C11.769 (2)C7—H7B0.9800
S1—C101.777 (2)C7—H7C0.9800
O3—C121.216 (3)C8—H8A0.9800
N1—C111.313 (3)C8—H8B0.9800
N1—C101.355 (3)C8—H8C0.9800
N2—C101.314 (3)C9—H9A0.9800
N2—N31.364 (3)C9—H9B0.9800
N3—C111.345 (3)C9—H9C0.9800
N3—C121.450 (3)C11—H110.9500
N4—C121.331 (3)C13—C141.511 (3)
N4—C131.468 (3)C13—H13A0.9900
N4—C151.473 (3)C13—H13B0.9900
C1—C21.408 (3)C14—H14A0.9800
C1—C61.414 (4)C14—H14B0.9800
C2—C31.387 (3)C14—H14C0.9800
C2—C71.509 (3)C15—C161.513 (4)
C3—C41.378 (4)C15—H15A0.9900
C3—H30.9500C15—H15B0.9900
C4—C51.385 (3)C16—H16A0.9800
C4—C81.499 (3)C16—H16B0.9800
C5—C61.387 (3)C16—H16C0.9800
C5—H50.9500
O1—S1—O2118.01 (13)H8A—C8—H8C109.5
O1—S1—C1111.37 (11)H8B—C8—H8C109.5
O2—S1—C1110.25 (12)C6—C9—H9A109.5
O1—S1—C10105.83 (12)C6—C9—H9B109.5
O2—S1—C10106.94 (11)H9A—C9—H9B109.5
C1—S1—C10103.17 (11)C6—C9—H9C109.5
C11—N1—C10101.98 (19)H9A—C9—H9C109.5
C10—N2—N3101.33 (18)H9B—C9—H9C109.5
C11—N3—N2109.55 (19)N2—C10—N1116.4 (2)
C11—N3—C12125.5 (2)N2—C10—S1121.10 (18)
N2—N3—C12124.48 (19)N1—C10—S1122.51 (17)
C12—N4—C13126.3 (2)N1—C11—N3110.7 (2)
C12—N4—C15115.5 (2)N1—C11—H11124.6
C13—N4—C15116.46 (19)N3—C11—H11124.6
C2—C1—C6120.9 (2)O3—C12—N4126.5 (2)
C2—C1—S1121.47 (19)O3—C12—N3116.5 (2)
C6—C1—S1117.58 (17)N4—C12—N3116.9 (2)
C3—C2—C1117.4 (2)N4—C13—C14112.9 (2)
C3—C2—C7116.8 (2)N4—C13—H13A109.0
C1—C2—C7125.8 (2)C14—C13—H13A109.0
C4—C3—C2123.1 (2)N4—C13—H13B109.0
C4—C3—H3118.4C14—C13—H13B109.0
C2—C3—H3118.4H13A—C13—H13B107.8
C3—C4—C5118.3 (2)C13—C14—H14A109.5
C3—C4—C8120.5 (2)C13—C14—H14B109.5
C5—C4—C8121.1 (2)H14A—C14—H14B109.5
C4—C5—C6122.0 (2)C13—C14—H14C109.5
C4—C5—H5119.0H14A—C14—H14C109.5
C6—C5—H5119.0H14B—C14—H14C109.5
C5—C6—C1118.2 (2)N4—C15—C16112.1 (2)
C5—C6—C9117.2 (2)N4—C15—H15A109.2
C1—C6—C9124.6 (2)C16—C15—H15A109.2
C2—C7—H7A109.5N4—C15—H15B109.2
C2—C7—H7B109.5C16—C15—H15B109.2
H7A—C7—H7B109.5H15A—C15—H15B107.9
C2—C7—H7C109.5C15—C16—H16A109.5
H7A—C7—H7C109.5C15—C16—H16B109.5
H7B—C7—H7C109.5H16A—C16—H16B109.5
C4—C8—H8A109.5C15—C16—H16C109.5
C4—C8—H8B109.5H16A—C16—H16C109.5
H8A—C8—H8B109.5H16B—C16—H16C109.5
C4—C8—H8C109.5
C10—N2—N3—C11−1.4 (3)N3—N2—C10—S1−177.87 (17)
C10—N2—N3—C12−174.3 (2)C11—N1—C10—N20.7 (3)
O1—S1—C1—C20.7 (2)C11—N1—C10—S1178.95 (19)
O2—S1—C1—C2133.7 (2)O1—S1—C10—N2113.2 (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—C667.9 (2)O2—S1—C10—N1168.3 (2)
C6—C1—C2—C32.1 (3)C1—S1—C10—N152.1 (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—N12.0 (3)
S1—C1—C2—C71.8 (3)C12—N3—C11—N1174.8 (2)
C1—C2—C3—C4−1.0 (4)C13—N4—C12—O3164.5 (3)
C7—C2—C3—C4179.6 (2)C15—N4—C12—O30.2 (4)
C2—C3—C4—C5−0.9 (4)C13—N4—C12—N3−17.0 (4)
C2—C3—C4—C8178.2 (2)C15—N4—C12—N3178.7 (2)
C3—C4—C5—C61.7 (4)C11—N3—C12—O3−29.9 (4)
C8—C4—C5—C6−177.4 (2)N2—N3—C12—O3141.9 (3)
C4—C5—C6—C1−0.6 (4)C11—N3—C12—N4151.5 (2)
C4—C5—C6—C9178.9 (2)N2—N3—C12—N4−36.8 (3)
C2—C1—C6—C5−1.3 (4)C12—N4—C13—C14110.4 (3)
S1—C1—C6—C5178.35 (18)C15—N4—C13—C14−85.5 (3)
C2—C1—C6—C9179.2 (2)C12—N4—C15—C1682.9 (3)
S1—C1—C6—C9−1.2 (3)C13—N4—C15—C16−83.0 (3)
N3—N2—C10—N10.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O2i0.952.383.136 (3)136
C7—H7C···Cg1ii0.982.803.561 (3)135
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O2i0.952.383.136 (3)136.3
C7—H7C···Cg1ii0.982.803.561 (3)135
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317).

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 71| Part 8| August 2015| Page o614
https://doi.org/10.1107/S2056989015013869
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