Ζ. Kristallogr.

NCS 215 (2000) 63-64 63

© by Oldenbourg Wissenschaftsverlag, München

Crystal structure of 3-(3-chloro-/7-tolyl)-l,l-dimethylurea, C10H13CIN2O

G. Pepe*· 1 , S. Veesler", J.-P. Astier", C. Corti" and G. Pfefer111

1
Universita de la Mediterranee, GCOPL, ESA-CNRS 6114, Campus de Luminy, Case 901, F-13288 Marseille Cedex 9, France
" Universites d'Aix-Marseille II et III, Centre de Recherche sur les Mecanismes de la Croissance Cristalline, Campus de Luminy, Case 913,
F-13288 Marseille Cedex 9, France
111
Rhone-Poulenc, CRIT, F-69151 Decines Charvieu Cedex, France

Received July 8, 1999, CCDC-No. 1267/218

Table 1. Data collection and handling.

Crystal: colourless, hexagonal prism,

size 0 . 1 6 x 0 . 1 8 x 0 . 2 5 mm
Wavelength: Mo Ka radiation (0.71073 A)
μ: 3.35 cm" 1
Diffractometer, scan mode: Enraf-Nonius CAD4, ω/2θ
20max: 60°
N(hkl)measured, N(hkl)unique: 3066, 3066
Criterion for I0bS, N(hkl)gc. /„ bs > 2 a(Iobs), 2773
N(param)Krmci. 166
Programs: DATARED [1] SHELXS-86 [2],
SHELXL-93 [3], ORTEPII [4]

Abstract
C10H13CIN2O, monoclinic, P12i/cl (No. 14), « = 7.758(1) Ä, Table 2. Atomic coordinates and displacement parameters (in A ).
b= 14.471(2) Ä, с = 9.432(1) Ä, β = 100.18(2)°, V= 1042.2 Ä 3 ,
Ζ = 4, Rp(F) = 0.043, wR(F2) = 0.086, Τ = 293 К. Atom Site X У ζ t/iso

H(l) 4e -0.937(1) -0.2218(8) -0.009(1) 0.05

Source of material
H(2) 4e -1.170(1) -0.3109(7) 0.005(1) 0.05
Chorotoluron, 3-(3-chloro-/?-tolyl)-l,l-dimethylurea, is a plant H(5) 4e -0.799(1) -0.4076(7) -0.283(1) 0.05
growth regulator. The raw industrial material, a white powder, is H(71) 4e -1.272(1) -0.5255(8) -0.063(1) 0.05
purified several times by recrystallization in monochlorobenzene H(72) 4e -1.364(2) -0.4387(8) -0.068(1) 0.05
in order to get pure single crystals (the solubility in this solvent H(73) 4e -1.370(2) -0.4710(7) -0.195(1) 0.05
H(9) 4e -0.653(1) -0.2657(7) -0.245(1) 0.05
being 6.35 g/1).
H(131) 4e -0.230(1) -0.1182(7) 0.000(1) 0.05
H(132) 4e -0.342(1) -0.0347(7) -0.045(1) 0.05
H(133) 4e -0.368(1) -0.0953(8) 0.069(1) 0.05
H(141) 4e -0.360(1) -0.2214(8) -0.271(1) 0.05
H(142) 4e -0.513(1) -0.1599(7) -0.338(1) 0.05
H(143) 4e -0.339(1) -0.1182(7) -0.280(1) 0.05

Table 3. Atomic coordinates and displacement parameters (in A 2 ).

Atom Site X У ζ Uи t/22 t/зз t/12 Uu t/23

C(l) 4e -0.9513(1) -0.27453(5) -0.06018(8) 0.0534(4) 0.0508(3) 0.0457(3) -0.0017(3) 0.0230(3) -0.0044(3)
C(2) 4e -1.0952(1) -0.32767(6) -0.04719(9) 0.0503(4) 0.0666(5) 0.0526(4) 0.0004(3) 0.0274(3) 0.0003(3)
C(3) 4e -1.13437(9) -0.41054(6) -0.11912(7) 0.0454(3) 0.0595(4) 0.0420(3) -0.0041(3) 0.0118(2) 0.0109(3)
C(4) 4e -1.01852(9) -0.43819(5) -0.20655(7) 0.0459(3) 0.0427(3) 0.0434(3) 0.0003(2) 0.0067(2) 0.0061(2)
C(5) 4e -0.87273(9) -0.38677(5) -0.22309(7) 0.0441(3) 0.0468(3) 0.0408(3) 0.0046(2) 0.0143(2) 0.0036(2)
C(6) 4e -0.83745(8) -0.30466(5) -0.14912(6) 0.0406(3) 0.0440(3) 0.0372(3) 0.0020(2) 0.0131(2) 0.0062(2)
C(7) 4e -1.2932(1) -0.46602(9) -0.1037(1) 0.0544(4) 0.0858(7) 0.0643(5) -0.0188(4) 0.0203(4) 0.0074(5)
Cl(8) 4e -1.05237(3) -0.54219(2) -0.29897(3) 0.0646(1) 0.0493(1) 0.0811(2) -0.00518(8) 0.0118(1) -0.00896(8)
N(9) 4e -0.69007(8) -0.25423(4) -0.17241(6) 0.0477(3) 0.0527(3) 0.0379(2) -0.0056(2) 0.0208(2) -0.0027(2)
C(10) 4e -0.59522(8) -0.19503(5) -0.07621(6) 0.0424(3) 0.0464(3) 0.0355(3) 0.0041(2) 0.0113(2) 0.0049(2)
O(ll) 4e -0.63276(8) -0.17966(4) 0.04276(5) 0.0579(3) 0.0634(3) 0.0362(2) -0.0025(2) 0.0178(2) -0.0019(2)
N(12) 4e -0.45798(8) -0.15352(5) -0.11954(7) 0.0472(3) 0.0700(4) 0.0430(3) -0.0131(3) 0.0164(2) -0.0077(3)
C(13) 4e -0.3438(1) -0.09526(8) -0.0201(1) 0.0543(4) 0.0706(5) 0.0630(5) -0.0138(4) 0.0179(3) -0.0169(4)
C(14) 4e -0.4110(1) -0.16590(9) -0.2598(1) 0.0622(5) 0.0847(6) 0.0519(4) -0.0197(4) 0.0269(4) -0.0067(4)

* Correspondence author (e-mail: pepe@chimir3.univ-mrs.fr)

64 3-(3-Chloro-p-tolyl)-1,1 -dimethylurea

References
1. Pepe, G : DATARED. Programs for X-ray Diffraction Data Reduction.
CRMC2-CNRS, Marseille 1979.
2. Sheldrick, G. M.: SHELX-86. Program for the Determination of Crystal
Structure. University of Göttingen, Germany 1985.
3. Sheldrick, G. M.: SHELXL-93. Program for the Refinement of Crystal
Structure. University of Göttingen, Germany 1993.
4. Johnson, C. K.: ORTEPII. Report ORNL- 3974, Oak Ridge National Lab-
oratory, Tennessee, USA 1976.