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organic papers
Acta Crystallographica Section E

Structure Reports Online
ISSN 1600-5368

NS,NO-Diphenyl(thiooxamide)

Victor B. Rybakov,* Eugene V. Babaev and Ylya V. Dlinnykh
Chemistry Department, Moscow State University, 119899 Moscow, Russia Correspondence e-mail: rybakov@biocryst.phys.msu.su

Key indicators Single-crystal X-ray study T = 293 K Ъ Mean ' (CБC) = 0.005 A R factor = 0.047 wR factor = 0.117 Data-to-parameter ratio = 9.7 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

The molecule of the title compound, PhNHC( S)C( O)NHPh or C14H12N2OS, consists of two planar fragments, one of which includes the central NHC( S)C( O)NH chain together with the Ph substituent on the C O side; the second Ph ring, the one on the C S side, all by itself, makes up the second planar fragment. Its plane is twisted about the N C bond by 52.87 (9) with respect to the plane of the ?rst fragment. The C S and C O double bonds adopt the transoid conformation with the torsion angle S C C O equal to Р179.6 (2) . The molecules in the crystal are linked into centrosymmetric dimers due to the N HСССO hydrogen bond involving the thioamide NH group.

Received 8 May 2001 Accepted 27 July 2001 Online 31 July 2001

Comment
The molecular structure of the title compound is shown in Fig. 1. The molecule consists of two planar fragments: the C9 C14 phenyl ring makes up one of them and the C3 C8 phenyl ring together with the N1 C1(O1) C2(S1) N2 chain atoms attached to C3 forms the other one. The intermolecular Ъ Ъ hydrogen bond [N2СССO1i 2.42 (3) A, N2СССO1i 3.136 (4) A i and N2 H2СССO1 148 (3) ; symmetry code: (i) 1 Р x, 1 Р y, Рz] links the molecules in the crystal into centrosymmetric dimers. In the thiooxamide part of the molecule, the S and O atoms are trans with respect to each other; the

# 2001 International Union of Crystallography Printed in Great Britain Б all rights reserved

torsion angle S1 C2 C1 O1 is Р179.6 (2) . The conjugation between the thioamide and amide moieties of the molЪ ecule is weak, as the C1 C2 bond [1.532 (4) A] is signi?cantly 2 2 longer than the standard Csp Csp bond length in conjuЪ gated systems (1.46 1.48 A; Allen et al., 1987). The bond Ъ Ъ distances C1 O1 [1.231 (3) A] and N1 C3 [1.413 (4) A] are Ъ ) and longer than the standard bond lengths for C O (1.22 A Ъ CAr Nsp2 (1.36 A) (Allen et al., 1987). This effect may be explained by a weak delocalization of electron density in the amide group. The bond angle C1 N1 C3 has an abnormal value of 131.5 (3) . This large bond angle may be explained by steric strain in the planar fragment O1 C1 N1 C3 C4 H4. The second phenyl ring (C9 C14) is twisted about the N2 C9 bond with respect to the planar moiety N2 C2(S1) C1(O1) N1 (C3 C8) by 52.87 (9) . Due to this twisting, the C2 N2 C9 bond angle is not distorted and has a generally accepted value of 126.1 (3) . Only one related structure
DOI: 10.1107/S1600536801012752 Acta Cryst. (2001). E57, o814 o815

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Victor B. Rybakov et al.

C14H12N2OS

organic papers
(Krayushkin et our case) was (Allen & Kenn molecule are compound. al., 1996) (with n-butyl instead of phenyl as in found in the Cambridge Structural Database ard, 1993). The main structural features of this essentially identical with those of the title

Experimental
A mixture of 0.5 g (2 mmol) 3 benzoxazolo[3,2 a]pyridinium 2 olate and 10 ml thionyl chloride (SOCl2) was kept under re?ux for 1 h. Thionyl chloride was evaporated and the precipitate obtained was washed with benzene (3 Т 10 ml) and dissolved in dichloromethane CH2Cl2 (20 ml). 0.4 g (4.3 mmol) aniline (C6H7N) was added to this solution. After heating at 313 K for 1 h and leaving to stand overnight at room temperature, the dichloromethane was evaporated, and the residue washed with water (3 Т 20 ml) and recrystallized from a mixture of chloroform and diethyl ether (4:1). The yield was 0.2 g (37%). Crystal data
C14H12N2OS Mr = 256.32 Monoclinic, P21/c Ъ a = 4.026 (5) A Ъ b = 14.682 (9) A Ъ c = 20.728 (12) A = 90.27 (2) Ъ V = 1225.1 (17) A3 Z=4 Dx = 1.390 Mg m 3 Mo K radiation Cell parameters from 25 re?ections = 13.0 15.0 " = 0.25 mm 1 T = 293 (2) K Prism, yellow 0.38 Т 0.12 Т 0.06 mm h k l 2 = 434 = 0 3 17 = 0 3 24 standard re?ections every 200 re?ections frequency: 60 min intensity decay: none

Figure 1
ORTEP with the the 30% arbitrary

3 (Farrugia, 1998) view of the molecule of the title compound atom numbering scheme. Displacement ellipsoids are drawn at probability level and H atoms are shown as small spheres of radii.

Table 2

Ъ Hydrogen bonding geometry (A, ).
DаHСССA N1аH1СС СS1 N2аH2СС СO1 C4аH4СССO1 N2аH2СС СO1i C14аH14СС СS1
Symmetry code: (i) 1

DаH 0.85 0.81 0.88 0.81 0.93
xY 1

HСССA 2.38 2.17 2.45 2.42 2.97 (3) (4) (3) (3) (3)

DСС СA 2.938 2.632 2.977 3.136 3.250 (3) (4) (4) (4) (4)

DаHСС СA 124 116 119 148 99 (3) (3) (3) (3) (2)

(3) (3) (3) (3) (3)
yY z.

Data collection
Enraf Nonius CAD-4 diffractometer 3 scans 2089 measured re?ections 2051 independent re?ections 1287 re?ections with I > 2' (I) Rint = 0.070 max = 25.0

All H atoms were re?ned isotropically; the C H bonds are in the Ъ range 0.82 1.00 A. Data collection: CAD 4 Software (Enraf Nonius, 1989); cell re?nement: CAD 4 Software; data reduction: WinGX98 (Farrugia, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re?ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP 3 (Farrugia, 1998).

Re?nement
Re?nement on F R[F 2 > 2' (F 2)] = 0.047 wR(F 2) = 0.117 S = 0.95 2051 re?ections 212 parameters
2

All H-atom parameters re?ned w = 1/[' 2(Fo2) + (0.0597P)2] where P = (Fo2 + 2Fc2)/3 (С/' )max = 0.048 Ъ С&max = 0.20 e A 3 Ъ С&min = 0.24 e A 3

This work has been supported by the Russian Foundation for Basic Research (project No. 99 03 33076). We also acknowledge the support of this Foundation in payment of the licence for using the Cambridge Structural Database (project No. 99 07 90133).

Table 1
S1аC2 O1аC1 C1аN1 C1аC2 N1аC3

Ъ Selected geometric parameters (A, ).
1.660 1.231 1.316 1.532 1.413 126.9 119.3 113.7 131.5 112.1 126.3 (3) (3) (4) (4) (4) (3) (3) (2) (3) (2) (2) N1аH1 C2аN2 N2аC9 N2аH2 C1аC2аS1 C2аN2аC9 C4аC3аN1 C8аC3аN1 C14аC9аN2 C10аC9аN2 0.85 (3) 1.310 (4) 1.428 (4) 0.81 (3) 121.6 126.1 123.0 117.0 120.2 119.2 (2) (3) (3) (3) (3) (3)

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. Allen, F. H. & Kennard, O. (1993). Chem. Des. Autom. News, 8, 1, 31 37. Enraf Nonius (1989). CAD-4 Software. Version 5.0. Enraf Nonius, Delft, The Netherlands. Farrugia, L. J. (1998). ORTEP-3 for Windows and WinGX98. University of Glasgow, Scotland. Krayushkin, M. M., Vorontsova, L. G., Kurella, M. G., Zavarzin, I. V. & Yarovenko, V. N. (1996). Russ. Chem. Bull. 2, 485 487. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Ш Gottingen, Germany.

O1аC1аN1 O1аC1аC2 N1аC1аC2 C1аN1аC3 N2аC2аC1 N2аC2аS1

Acta Cryst. (2001). E57, o814 o815

Victor B. Rybakov et al.

C14H12N2OS

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