A second monoclinic polymorph of N-(diethyl­amino­thio­carbon­yl)-N′-phenyl­benzamidine

Schröder, B.; Gomes, L.R.; Santos, L.M.N.B.F.; Brandão, P.; Low, J.N.

doi:10.1107/S1600536811010464

Volume 67
Part 4
Pages o962-o963
April 2011

Received 5 March 2011
Accepted 20 March 2011
Online 26 March 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R = 0.056
wR = 0.142
Data-to-parameter ratio = 17.4
Details

A second monoclinic polymorph of N-(diethylaminothiocarbonyl)-N'-phenylbenzamidine

Bernd Schröder,^a Ligia R. Gomes,^b Luís M. N. B. F. Santos,^c Paula Brandão ^a and John Nicolson Low ^d ^*

^aCICECO, Departamento de Química, Faculdade de Ciências, Universidade do Aveiro, 3810-193 Aveiro, Portugal,^bREQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, P-4169_007 Porto, Portugal,^cCentro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, P-4169_007 Porto, Portugal, and ^dDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland
Correspondence e-mail: jnlow111@gmail.com

The asymmetric unit of the title compound, C₁₈H₂₁N₃S, contains five molecules. The equivalent bond distances in the five molecules are in excellent agreement, the r.m.s. fit being within 0.007 Å. The five molecules are linked into a chain consisting of alternating pseudo-enantiomers by N-HS hydrogen bonds supplemented by weak C-H [pi] interactions. The action of a glide plane links the asymmetric unit into an extended chain. A polymorph of the title compound with one molecule in the asymmetric unit was reported by Braun et al. [Cryst. Res. Technol. (1988), 23, 35-39].

Related literature

For the structure of the first polymorph, see: Braun et al. (1988). For graph-set analysis, see: Bernstein et al. (1995). For a description of the Cambridge Structural Database, see: Allen (2002). Preparative details can be found in Beyer et al. (1984).

Experimental

Crystal data

C₁₈H₂₁N₃S
M_r = 311.44
Monoclinic, P 2₁ /c
a = 21.2894 (8) Å
b = 18.8015 (7) Å
c = 27.1792 (10) Å
= 128.584 (2)°
V = 8504.1 (5) Å³
Z = 20
Mo K radiation
= 0.19 mm^-1
T = 150 K
0.20 × 0.06 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.963, T_max = 0.994
54002 measured reflections
17402 independent reflections
9835 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.142
S = 1.01
17398 reflections
1001 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg4, Cg5, Cg8 and Cg10 are the centroids of the C121-C126, C221-C226, C321-C326, C421-C426 and C521-C526 rings, respectively.

D-HA	D-H	HA	DA	D-HA
N11-H11S24	0.86	2.62	3.440 (2)	159
N21-H21S34	0.86	2.60	3.407 (2)	157
N31-H31S44	0.86	2.64	3.459 (2)	161
N41-H41S54	0.86	2.62	3.416 (2)	155
N51-H51S14ⁱ	0.86	2.62	3.431 (2)	157
C26-H26BCg2	0.99	2.91	3.594 (4)	127
C36-H36ACg4	0.99	2.86	3.575 (4)	130
C46-H46BCg6	0.99	2.84	3.549 (4)	129
C56-H56ACg8	0.99	2.89	3.566 (4)	126
C16-H16ACg10ⁱⁱ	0.99	2.86	3.552 (4)	128
Symmetry codes: (i) $[x+2, -y+{\script{1\over 2}}, z+{\script{3\over 2}}]$ ; (ii) $[x-2, -y-{\script{1\over 2}}, z-{\script{5\over 2}}]$ .

Data collection: APEX2 and SMART (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and OSCAIL (McArdle et al., 2004); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2413 ).

Acknowledgements

BS acknowledges the FCT and the European Social Fund (ESF) under the third Community Support Framework (CSF) for the award of a post-doctoral research grant (SFRH/BPD/38637/2007).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Bernstein, J., Davis, R. E., Shimoni, I. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Beyer, L., Hartung, J. & Widera, R. (1984). Tetrahedron, 40, 405-412.
Braun, U., Sieler, J., Richter, R., Leba, I. & Golic, L. (1988). Cryst. Res. Technol. 23, 35-39.
Bruker (2004). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
McArdle, P., Gilligan, K., Cunningham, D., Dark, R. & Mahon, M. (2004). CrystEngComm, 6, 303-309.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds