1,3-Diphenyl­propan-2-one (2,4-dinitro­phen­yl)hydrazone

Gomes, L.R.; Lima, C.F.R.A.C.; Santos, L.M.N.B.F.; Brandão, P.; Low, J.N.

doi:10.1107/S1600536810002746

Volume 66
Part 3
Page o565
March 2010

Received 19 January 2010
Accepted 21 January 2010
Online 10 February 2010

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.126
Data-to-parameter ratio = 19.0
Details

1,3-Diphenylpropan-2-one (2,4-dinitrophenyl)hydrazone

Ligia R. Gomes,^a Carlos F. R. A. C. Lima,^b Luís M. N. B. F. Santos,^b Paula Brandão ^c and John Nicolson Low ^d ^*

^aREQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, P-4169_007 Porto, Portugal,^bCentro 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,^cCICECO, Departamento de Química, Universidade de Aviero, 3810-193 Aveiro, Portugal, and ^dDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland.
Correspondence e-mail: che562@abdn.ac.uk

In the title compound, C₂₁H₁₈N₄O₄, there is an intramolecular N-HO hydrogen bond between the amino H atom and an O atom of the 2-nitro group of the adjacent benzene ring. The central benzene ring forms dihedral angles of 79.98 (7) and 82.88 (7)° with the two phenyl rings. In the crystal structure, molecules are linked into a three-dimensional network by weak C-HN, C-HO and C-H [pi] interactions.

Related literature

For the structures of related 2,4-dinitrophenyl hydrazines, see: Wardell et al. (2006); Lima et al. (2009). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₁H₁₈N₄O₄
M_r = 390.39
Monoclinic, P 2₁ /c
a = 17.2448 (9) Å
b = 5.1013 (2) Å
c = 22.7459 (13) Å
= 109.475 (2)°
V = 1886.49 (16) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 150 K
0.40 × 0.06 × 0.02 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.962, T_max = 0.998
13123 measured reflections
4973 independent reflections
3417 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.126
S = 1.04
4973 reflections
262 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg31 and Cg41 are the centroids of the C31-C36 and C41-C46 phenyl rings, respectively.

D-HA	D-H	HA	DA	D-HA
N1-H1O122	0.91	1.92	2.5976 (15)	129
C15-H15O142ⁱ	0.95	2.44	3.314 (2)	153
C3-H3AN2ⁱⁱ	0.99	2.53	3.3811 (18)	144
C3-H3BO121ⁱⁱⁱ	0.99	2.55	3.3138 (18)	134
C4-H4BCg41^iv	0.99	2.79	3.7438 (16)	163
C45-H45Cg31^v	0.95	2.92	3.7424 (18)	145
Symmetry codes: (i) -x+1, -y+3, -z+1; (ii) x, y-1, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x, y+1, z; (v) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and 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: LH2985 ).

Acknowledgements

CFRACL thanks the FCT and the European Social Fund (ESF) under the third Community Support Framework (CSF) for the award of a PhD Research Grant (SRFH/BD/29394/2006). LRG thanks the Fundação para o Ensino e Cultura Fernando Pessoa.

References

Bernstein, J., Davis, R. E., Shimoni, I. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Lima, C. F. R. A. C., Gomes, L. R., Santos, L. M. N. B. F., Rodriguez-Borges, J. E. & Low, J. N. (2009). Acta Cryst. E65, o2729.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o318-o320.

organic compounds