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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1218.
Published online 2008 June 7. doi:  10.1107/S1600536808016462
PMCID: PMC2961706

1-(2-Chloro­benzo­yl)-3-[4-(trifluoro­meth­oxy)phen­yl]urea

Abstract

The title compound, C15H10ClF3N2O3, is considered to belong to a fourth generation of insecticides with properties such as high selectivity, low acute toxicity for mammals and high biological activity. The dihedral angle between the two benzene rings is 59.3 (2)°. Intra­molecular C—H(...)O and N—H(...)O hydrogen bonds are observed. Inter­molecular N—H(...)O hydrogen bonding generates a centrosymmetric dimer. The F atoms are disordered over two positions; the site occupancy factors are 0.52 and 0.48.

Related literature

For related literature, see: Allen et al. (1987 [triangle]); Wang et al. (1998 [triangle]); Qiu et al. (12004 [triangle]).

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Object name is e-64-o1218-scheme1.jpg

Experimental

Crystal data

  • C15H10ClF3N2O3
  • M r = 358.70
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1218-efi1.jpg
  • a = 17.293 (4) Å
  • b = 8.2870 (17) Å
  • c = 11.073 (2) Å
  • β = 101.74 (3)°
  • V = 1553.6 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 298 (2) K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.917, T max = 0.943
  • 2946 measured reflections
  • 2784 independent reflections
  • 1906 reflections with I > 2σ(I)
  • R int = 0.012
  • 3 standard reflections every 200 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.079
  • wR(F 2) = 0.186
  • S = 1.01
  • 2784 reflections
  • 209 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.58 e Å−3
  • Δρmin = −0.38 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 global, I. DOI: 10.1107/S1600536808016462/kp2174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016462/kp2174Isup2.hkl

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

Acknowledgments

The authors thank Professor Yuan-wen Wu of Nanjing University of Technology for his kind help with the crystal structure analysis.

supplementary crystallographic information

Comment

The title compound, (I), is generally recognized as an insect growth regulator that interferes with chitin synthesis in target pests causing death or abortive development (Wang et al., 1998). As part of our studies in this area, we report herein the crystal structure of the title compound (I).

In the molecule of (I) (Fig.1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The intramolecular C—H···O and N—H···O hydrogen bonds are observed (Fig. 1, Table 1). Intermolecular N—H···O hydrogen bond generates a cyclic, centrosymmetric hydrogen bonded dimer (Table 1, Fig. 2).

Experimental

The title compound, (I), was prepared according to the literature method (Qiu et al., 1981). 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 6 d.

Refinement

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

Trifloromethyl group was disordered over two sites, occupancies were refined and converged to 0.52 and 0.48, respectively.

Figures

Fig. 1.
The molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Intramolecular hydrogen bonds are shown by dased lines.
Fig. 2.
The crystal packing diagram with hydrogen bonds drawn as dashed lines.

Crystal data

C15H10ClF3N2O3F000 = 728
Mr = 358.70Dx = 1.534 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 17.293 (4) Åθ = 10–14º
b = 8.2870 (17) ŵ = 0.30 mm1
c = 11.073 (2) ÅT = 298 (2) K
β = 101.74 (3)ºBlock, colourless
V = 1553.6 (6) Å30.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.012
Radiation source: fine-focus sealed tubeθmax = 25.2º
Monochromator: graphiteθmin = 1.2º
T = 298(2) Kh = −20→20
ω/2θ scansk = 0→9
Absorption correction: ψ scan(North et al., 1968)l = 0→13
Tmin = 0.917, Tmax = 0.9433 standard reflections
2946 measured reflections every 200 reflections
2784 independent reflections intensity decay: none
1906 reflections with I > 2σ(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)] = 0.079H-atom parameters constrained
wR(F2) = 0.186  w = 1/[σ2(Fo2) + (0.06P)2 + 3P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2784 reflectionsΔρmax = 0.58 e Å3
209 parametersΔρmin = −0.37 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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)
Cl0.39377 (8)0.46678 (16)0.93229 (10)0.0767 (4)
F10.9765 (5)0.8806 (12)0.8631 (10)0.1470.52
F20.9962 (5)0.7066 (11)0.7283 (8)0.1310.52
F31.0673 (5)0.7391 (10)0.9039 (8)0.1270.52
F1'0.9962 (6)0.8363 (13)0.9452 (9)0.1450.48
F2'0.9788 (6)0.7985 (12)0.7564 (10)0.1400.48
F3'1.0763 (4)0.6519 (9)0.8854 (7)0.1110.48
O10.9560 (2)0.6074 (6)0.8858 (4)0.1185 (16)
O20.59902 (15)0.5358 (4)0.5609 (2)0.0661 (8)
O30.50002 (17)0.7159 (4)0.8415 (3)0.0733 (9)
N10.62777 (18)0.6359 (4)0.7569 (3)0.0578 (9)
H1A0.60610.67320.81450.069*
N20.49834 (18)0.6012 (4)0.6534 (3)0.0552 (8)
H2A0.46650.56910.58760.066*
C10.9996 (3)0.7289 (13)0.8574 (9)0.146 (3)
C20.8720 (3)0.6213 (7)0.8485 (5)0.0820 (15)
C30.8311 (3)0.6917 (7)0.9265 (5)0.0849 (16)
H3A0.85730.73531.00100.102*
C40.7488 (3)0.6978 (6)0.8930 (4)0.0742 (13)
H4A0.71940.74660.94450.089*
C50.7113 (2)0.6298 (5)0.7812 (3)0.0570 (10)
C60.7545 (2)0.5566 (6)0.7047 (4)0.0694 (12)
H6A0.72940.50920.63100.083*
C70.8363 (3)0.5553 (7)0.7400 (5)0.0802 (14)
H7A0.86660.50880.68880.096*
C80.5786 (2)0.5883 (5)0.6510 (4)0.0532 (10)
C90.4632 (2)0.6571 (5)0.7445 (4)0.0527 (9)
C100.3755 (2)0.6418 (5)0.7208 (4)0.0539 (10)
C110.3384 (2)0.5638 (5)0.8036 (4)0.0561 (10)
C120.2570 (3)0.5556 (6)0.7844 (5)0.0755 (13)
H12A0.23270.50310.84100.091*
C130.2120 (3)0.6263 (7)0.6803 (5)0.0842 (15)
H13A0.15720.62270.66720.101*
C140.2478 (3)0.7012 (7)0.5968 (5)0.0842 (15)
H14A0.21720.74770.52670.101*
C150.3293 (3)0.7087 (6)0.6157 (4)0.0687 (12)
H15A0.35320.75880.55760.082*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl0.0925 (9)0.0813 (8)0.0561 (6)0.0109 (7)0.0145 (6)0.0084 (6)
F10.1470.1470.1470.0000.0300.000
F20.1310.1310.1310.0000.0270.000
F30.1270.1270.1270.0000.0260.000
F1'0.1450.1450.1450.0000.0300.000
F2'0.1400.1400.1400.0000.0290.000
F3'0.1110.1110.1110.0000.0230.000
O10.0479 (19)0.170 (4)0.123 (3)−0.013 (2)−0.017 (2)0.038 (3)
O20.0487 (15)0.092 (2)0.0543 (16)−0.0083 (15)0.0024 (13)−0.0147 (16)
O30.0656 (18)0.083 (2)0.0648 (18)−0.0052 (16)−0.0016 (15)−0.0225 (17)
N10.0467 (18)0.072 (2)0.0491 (18)−0.0096 (16)−0.0039 (14)−0.0009 (17)
N20.0502 (18)0.064 (2)0.0468 (17)−0.0067 (16)−0.0008 (14)−0.0074 (16)
C10.025 (2)0.234 (10)0.168 (7)−0.022 (4)−0.005 (3)0.020 (8)
C20.050 (3)0.106 (4)0.080 (3)−0.017 (3)−0.010 (2)0.024 (3)
C30.056 (3)0.126 (5)0.063 (3)−0.028 (3)−0.012 (2)0.007 (3)
C40.062 (3)0.097 (4)0.059 (3)−0.023 (3)−0.002 (2)−0.001 (2)
C50.052 (2)0.066 (3)0.048 (2)−0.014 (2)−0.0026 (18)0.0114 (19)
C60.049 (2)0.089 (3)0.063 (3)−0.003 (2)−0.004 (2)0.002 (2)
C70.055 (3)0.098 (4)0.084 (3)−0.001 (3)0.006 (2)0.004 (3)
C80.049 (2)0.059 (2)0.047 (2)−0.0097 (19)0.0009 (17)−0.0001 (19)
C90.056 (2)0.046 (2)0.052 (2)−0.0018 (18)0.0009 (18)0.0000 (18)
C100.053 (2)0.047 (2)0.058 (2)0.0019 (18)0.0017 (18)−0.0064 (19)
C110.063 (2)0.055 (3)0.051 (2)0.0033 (19)0.0140 (19)−0.0095 (19)
C120.066 (3)0.082 (3)0.083 (3)0.002 (3)0.027 (3)−0.007 (3)
C130.057 (3)0.098 (4)0.097 (4)0.007 (3)0.013 (3)−0.011 (3)
C140.071 (3)0.088 (4)0.082 (3)0.022 (3)−0.011 (3)0.002 (3)
C150.061 (3)0.077 (3)0.064 (3)0.005 (2)0.003 (2)0.012 (2)

Geometric parameters (Å, °)

Cl—C111.743 (4)C3—C41.397 (6)
F1—C11.324 (12)C3—H3A0.9300
F2—C11.431 (11)C4—C51.394 (6)
F3—C11.181 (10)C4—H4A0.9300
F1'—C11.327 (12)C5—C61.379 (6)
F2'—C11.244 (11)C6—C71.389 (6)
F3'—C11.447 (10)C6—H6A0.9300
O1—C11.334 (9)C7—H7A0.9300
O1—C21.432 (5)C9—C101.490 (5)
O2—C81.205 (4)C10—C111.382 (6)
O3—C91.233 (4)C10—C151.386 (5)
N1—C81.360 (5)C11—C121.381 (6)
N1—C51.416 (5)C12—C131.383 (7)
N1—H1A0.8600C12—H12A0.9300
N2—C91.361 (5)C13—C141.362 (7)
N2—C81.398 (5)C13—H13A0.9300
N2—H2A0.8600C14—C151.384 (6)
C2—C71.350 (7)C14—H14A0.9300
C2—C31.354 (7)C15—H15A0.9300
C1—O1—C2117.4 (5)C5—C4—H4A120.5
C8—N1—C5126.0 (4)C3—C4—H4A120.5
C8—N1—H1A117.0C6—C5—C4120.8 (4)
C5—N1—H1A117.0C6—C5—N1123.9 (4)
C9—N2—C8129.5 (3)C4—C5—N1115.2 (4)
C9—N2—H2A115.3C5—C6—C7118.6 (4)
C8—N2—H2A115.3C5—C6—H6A120.7
F3—C1—F2'115.9 (9)C7—C6—H6A120.7
F3—C1—F1101.2 (9)C2—C7—C6120.2 (5)
F2'—C1—F164.4 (8)C2—C7—H7A119.9
F3—C1—F1'79.7 (8)C6—C7—H7A119.9
F2'—C1—F1'107.4 (11)O2—C8—N1125.6 (4)
F1—C1—F1'43.2 (6)O2—C8—N2120.2 (3)
F3—C1—O1120.6 (9)N1—C8—N2114.2 (4)
F2'—C1—O1119.2 (7)O3—C9—N2123.4 (4)
F1—C1—O1121.0 (7)O3—C9—C10120.9 (4)
F1'—C1—O1102.8 (8)N2—C9—C10115.7 (3)
F3—C1—F2106.3 (8)C11—C10—C15118.6 (4)
F2'—C1—F238.4 (6)C11—C10—C9121.1 (3)
F1—C1—F2102.6 (9)C15—C10—C9120.4 (4)
F1'—C1—F2145.0 (11)C12—C11—C10121.1 (4)
O1—C1—F2103.1 (8)C12—C11—Cl118.5 (4)
F3—C1—F3'32.4 (5)C10—C11—Cl120.4 (3)
F2'—C1—F3'118.7 (9)C11—C12—C13119.4 (5)
F1—C1—F3'132.9 (8)C11—C12—H12A120.3
F1'—C1—F3'108.3 (8)C13—C12—H12A120.3
O1—C1—F3'98.9 (8)C14—C13—C12120.2 (5)
F2—C1—F3'90.4 (7)C14—C13—H13A119.9
C7—C2—C3122.6 (4)C12—C13—H13A119.9
C7—C2—O1118.5 (5)C13—C14—C15120.5 (5)
C3—C2—O1118.8 (5)C13—C14—H14A119.7
C2—C3—C4118.8 (4)C15—C14—H14A119.7
C2—C3—H3A120.6C14—C15—C10120.3 (5)
C4—C3—H3A120.6C14—C15—H15A119.9
C5—C4—C3119.0 (5)C10—C15—H15A119.9

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.861.952.653 (4)138
N2—H2A···O2i0.862.002.851 (4)172
C6—H6A···O20.932.242.838 (5)121

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2174).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Qiu, S. S., Li, X. Z., Zhang, S. H. & Gao, X. F. (2004). J. Xiandai Nongyao 3, 17–18.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, S., Allan, R. D., Skerritt, J. H. & Kennedy, I. R. (1998). J. Agric. Food Chem.46, 3330–3338.

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