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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1220.
Published online 2008 June 7. doi:  10.1107/S1600536808016656
PMCID: PMC2961899

N,N-Dimethyl-N′-[3-(trifluoro­methyl)­phenyl]­urea

Abstract

The title compound, C10H11F3N2O, is an important urea-based herbicide. In the crystal structure, the mol­ecular packing is stabilized by two intra­molecular C—H(...)O hydrogen bonds and one inter­molecular N—H(...)O hydrogen bond, generating a C(4) graph-set motif running parallel to the [001] direction. The F atoms are disordered over two sites, with occupancies of 0.176 (9) and 0.824 (9).

Related literature

For related literature, see: Bernstein et al. (1995 [triangle]); Xu et al. (2005 [triangle]); Zhao & Wilkins (2003 [triangle]); Li et al. (2007 [triangle]).

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Object name is e-64-o1220-scheme1.jpg

Experimental

Crystal data

  • C10H11F3N2O
  • M r = 232.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1220-efi1.jpg
  • a = 11.005 (2) Å
  • b = 9.991 (2) Å
  • c = 10.012 (2) Å
  • β = 96.89 (3)°
  • V = 1092.9 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 298 (2) K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD4 diffractometer
  • Absorption correction: multi-scan (North et al., 1968 [triangle]) T min = 0.963, T max = 0.987
  • 2076 measured reflections
  • 1953 independent reflections
  • 1335 reflections with I > 2σi(I)
  • R int = 0.020
  • 3 standard reflections every 200 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.137
  • S = 1.00
  • 1953 reflections
  • 169 parameters
  • 36 restraints
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808016656/bx2148sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016656/bx2148Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound, (I), is a pre- and postemergence herbicide used widely as water dispersible and suspension concentrate formulations for the control of grass and broadleaf weeds in cotton and sugarcane (Zhao & Wilkins, 2003). As part of our studies in this area (Li et al., 2007), we report herein the crystal structure of the title compound, (I), Fig 1. In the crystal structure the molecular packing is stabilized by two intramolecular C—H···O as well as one intermolecular N—H···O hydrogen bond generating a graph-set motif C(4) running parallel to [001] direction (Bernstein et al., 1995), Table 1.

Experimental

The title compound, (I), was prepared according to the literature method (Xu et al., 2005). The crystals suitable for X-ray analysis were obtained by dissolving (I) (0.1 g, in acetonitrile (25 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Refinement

H atoms were positioned geometrically, C—H = 0.86, 0.93 and 0.96 Å for amido, aromatic and methyl H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Trifloromethyl group was disordered over two sites, occupancies were refined and converged to 0.176 (9) and 0.824 (9), respectively.

Figures

Fig. 1.
The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
The molecule packing diagram.

Crystal data

C10H11F3N2OF000 = 480
Mr = 232.20Dx = 1.411 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.005 (2) Åθ = 10–13º
b = 9.991 (2) ŵ = 0.13 mm1
c = 10.012 (2) ÅT = 298 (2) K
β = 96.89 (3)ºNeedle, colourless
V = 1092.9 (4) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD4 diffractometerRint = 0.020
Radiation source: fine-focus sealed tubeθmax = 25.2º
Monochromator: graphiteθmin = 1.9º
T = 298(2) Kh = −13→13
ω/2θ scansk = −11→0
Absorption correction: multi-scan(North et al., 1968)l = 0→11
Tmin = 0.963, Tmax = 0.9873 standard reflections
2076 measured reflections every 200 reflections
1953 independent reflections intensity decay: none
1335 reflections with I > 2σi(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.137  w = 1/[σ2(Fo2) + (0.050P)2 + 0.630P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
1953 reflectionsΔρmax = 0.19 e Å3
169 parametersΔρmin = −0.15 e Å3
36 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.162 (9)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
C1−0.4416 (3)0.3310 (5)0.7481 (4)0.083
F1−0.4245 (19)0.355 (3)0.6336 (15)0.097 (6)0.176 (9)
F2−0.444 (2)0.1924 (18)0.754 (3)0.127 (8)0.176 (9)
F3−0.5413 (13)0.368 (3)0.773 (2)0.102 (6)0.176 (9)
F1'−0.4988 (5)0.4328 (5)0.6794 (6)0.149 (2)0.824 (9)
F2'−0.4081 (3)0.2491 (7)0.6573 (5)0.126 (2)0.824 (9)
F3'−0.5304 (4)0.2692 (7)0.8022 (4)0.1244 (19)0.824 (9)
O−0.00769 (19)0.2044 (2)0.79738 (17)0.0702 (7)
N1−0.0375 (2)0.2618 (2)1.0096 (2)0.0532 (7)
H1A−0.01060.25481.09350.064*
N20.1237 (2)0.1254 (3)0.9701 (2)0.0569 (7)
C2−0.3406 (3)0.3766 (3)0.8510 (3)0.0553 (8)
C3−0.2362 (2)0.2993 (3)0.8761 (3)0.0508 (7)
H3A−0.22800.22110.82770.061*
C4−0.1437 (2)0.3397 (3)0.9745 (2)0.0460 (7)
C5−0.1575 (3)0.4563 (3)1.0448 (3)0.0572 (8)
H5A−0.09540.48401.11020.069*
C6−0.2618 (3)0.5322 (3)1.0194 (3)0.0649 (9)
H6A−0.27030.61031.06800.078*
C7−0.3543 (3)0.4927 (3)0.9216 (3)0.0627 (9)
H7A−0.42490.54390.90370.075*
C80.0253 (2)0.1970 (3)0.9195 (2)0.0492 (7)
C90.1950 (3)0.0560 (4)0.8790 (3)0.0814 (11)
H9A0.15920.07060.78790.122*
H9B0.1957−0.03810.89830.122*
H9C0.27730.08960.89030.122*
C100.1652 (3)0.1137 (4)1.1124 (3)0.0765 (11)
H10A0.09720.09131.15990.115*
H10B0.19970.19741.14540.115*
H10C0.22620.04481.12640.115*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0590.1000.086−0.002−0.002−0.005
F10.102 (10)0.117 (11)0.066 (7)−0.013 (8)−0.012 (6)−0.014 (7)
F20.118 (11)0.114 (10)0.134 (12)−0.017 (8)−0.041 (8)−0.013 (8)
F30.052 (7)0.134 (11)0.115 (10)−0.004 (8)−0.004 (6)−0.016 (9)
F1'0.135 (4)0.122 (3)0.162 (4)0.004 (3)−0.093 (3)0.022 (3)
F2'0.073 (2)0.192 (5)0.105 (3)0.005 (3)−0.0191 (18)−0.077 (4)
F3'0.081 (2)0.153 (4)0.140 (3)−0.058 (3)0.014 (2)−0.016 (3)
O0.0692 (13)0.1123 (19)0.0284 (10)0.0120 (12)0.0031 (9)−0.0004 (10)
N10.0590 (14)0.0718 (16)0.0269 (10)0.0113 (13)−0.0028 (10)−0.0003 (11)
N20.0562 (14)0.0701 (17)0.0433 (13)0.0112 (13)0.0017 (11)−0.0004 (12)
C20.0476 (16)0.067 (2)0.0508 (16)−0.0061 (15)0.0040 (13)0.0053 (15)
C30.0542 (17)0.0543 (17)0.0430 (15)−0.0044 (14)0.0027 (12)−0.0013 (13)
C40.0501 (15)0.0563 (17)0.0312 (12)0.0004 (13)0.0040 (11)0.0034 (12)
C50.0628 (18)0.066 (2)0.0417 (15)−0.0010 (16)0.0002 (13)−0.0058 (14)
C60.074 (2)0.063 (2)0.0579 (18)0.0033 (17)0.0088 (16)−0.0090 (15)
C70.0570 (18)0.068 (2)0.0637 (19)0.0106 (16)0.0093 (15)0.0088 (17)
C80.0505 (16)0.0645 (18)0.0323 (14)−0.0022 (14)0.0039 (11)0.0020 (12)
C90.078 (2)0.098 (3)0.071 (2)0.022 (2)0.0198 (18)−0.004 (2)
C100.079 (2)0.095 (3)0.0517 (18)0.023 (2)−0.0079 (16)0.0085 (18)

Geometric parameters (Å, °)

C1—F11.208 (16)C2—C31.382 (4)
C1—F31.214 (15)C3—C41.389 (4)
C1—F2'1.308 (5)C3—H3A0.9300
C1—F3'1.325 (6)C4—C51.380 (4)
C1—F1'1.341 (6)C5—C61.374 (4)
C1—F21.386 (18)C5—H5A0.9300
C1—C21.494 (5)C6—C71.383 (4)
O—C81.235 (3)C6—H6A0.9300
N1—C81.364 (3)C7—H7A0.9300
N1—C41.412 (3)C9—H9A0.9600
N1—H1A0.8600C9—H9B0.9600
N2—C81.345 (3)C9—H9C0.9600
N2—C101.448 (4)C10—H10A0.9600
N2—C91.449 (4)C10—H10B0.9600
C2—C71.376 (4)C10—H10C0.9600
F1—C1—F3112.7 (14)C2—C3—C4119.3 (3)
F1—C1—F2'51.4 (11)C2—C3—H3A120.3
F3—C1—F2'132.5 (9)C4—C3—H3A120.3
F1—C1—F3'133.4 (8)C5—C4—C3119.4 (3)
F3—C1—F3'47.9 (13)C5—C4—N1118.5 (2)
F2'—C1—F3'106.1 (5)C3—C4—N1122.1 (2)
F1—C1—F1'58.6 (12)C6—C5—C4120.8 (3)
F3—C1—F1'59.6 (12)C6—C5—H5A119.6
F2'—C1—F1'105.8 (5)C4—C5—H5A119.6
F3'—C1—F1'103.9 (4)C5—C6—C7120.1 (3)
F1—C1—F2104.2 (15)C5—C6—H6A120.0
F3—C1—F2106.2 (16)C7—C6—H6A120.0
F2'—C1—F254.1 (12)C2—C7—C6119.2 (3)
F3'—C1—F260.0 (12)C2—C7—H7A120.4
F1'—C1—F2140.5 (8)C6—C7—H7A120.4
F1—C1—C2113.9 (8)O—C8—N2122.2 (3)
F3—C1—C2112.2 (9)O—C8—N1120.9 (3)
F2'—C1—C2114.9 (3)N2—C8—N1116.9 (2)
F3'—C1—C2112.6 (4)N2—C9—H9A109.5
F1'—C1—C2112.7 (4)N2—C9—H9B109.5
F2—C1—C2106.8 (8)H9A—C9—H9B109.5
C8—N1—C4124.5 (2)N2—C9—H9C109.5
C8—N1—H1A117.7H9A—C9—H9C109.5
C4—N1—H1A117.7H9B—C9—H9C109.5
C8—N2—C10123.9 (2)N2—C10—H10A109.5
C8—N2—C9119.3 (2)N2—C10—H10B109.5
C10—N2—C9116.8 (3)H10A—C10—H10B109.5
C7—C2—C3121.2 (3)N2—C10—H10C109.5
C7—C2—C1119.6 (3)H10A—C10—H10C109.5
C3—C2—C1119.3 (3)H10B—C10—H10C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···Oi0.862.082.880 (3)155
C3—H3A···O0.932.482.884 (3)106
C9—H9A···O0.962.282.721 (4)107

Symmetry codes: (i) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2148).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Li, F. S., Sun, F., Liu, X. J. & Cui, H. H. (2007). Agric. Sci. China, 6, 964–969.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xu, X. S., Du, X. H., Hu, Z. Y. & Xu, Z. Y. (2005). Nongyao, 44, 210–211.
  • Zhao, J. & Wilkins, R. M. (2003). J. Agric. Food Chem.51, 4023–4028. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography