(E)-Methyl N′-(4-bromo­benzyl­idene)­hydrazinecarboxyl­ate at 123 K

Sun, R.; Cheng, X.-W.

doi:10.1107/S1600536808021983

Volume 64
Part 8
Page o1544
August 2008

Received 12 July 2008
Accepted 14 July 2008
Online 19 July 2008

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.005 Å
R = 0.037
wR = 0.099
Data-to-parameter ratio = 14.2
Details

(E)-Methyl N'-(4-bromobenzylidene)hydrazinecarboxylate at 123 K

Rong Sun ^a and Xiang-Wei Cheng ^a ^*

^aZhejiang Police College Experience Center, Zhejiang Police College, Hangzhou 310053, People's Republic of China
Correspondence e-mail: zpccxw@126.com

The title compound, C₉H₉BrN₂O₂, crystallizes with two independent but essentially identical molecules in the asymmetric unit. Each molecule adopts a trans configuration with respect to the C=N bond. In one of the molecules, the dihedral angle between the benzene ring and the hydrazinecarboxylic acid plane is 24.9 (2)°, and that in the other molecule is 16.1 (2)°. The molecules are linked into a three-dimensional network via intermolecular N-HO, C-HO, C-HN and C-HBr hydrogen bonds. An intramolecular N-HO hydrogen bond is also present.

Related literature

For general background, see: Parashar et al. (1988); Hadjoudis et al. (1987); Borg et al. (1999). For a related structure, see: Cheng (2008).

Experimental

Crystal data

C₉H₉BrN₂O₂
M_r = 257.09
Monoclinic, P 2₁ /c
a = 13.8585 (10) Å
b = 9.5257 (7) Å
c = 15.5871 (11) Å
= 95.967 (3)°
V = 2046.5 (3) Å³
Z = 8
Mo K radiation
= 3.99 mm^-1
T = 123 (2) K
0.30 × 0.26 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.320, T_max = 0.367
20978 measured reflections
3610 independent reflections
2615 reflections with I > 2(I)
R_int = 0.056

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.099
S = 1.05
3610 reflections
254 parameters
H-atom parameters constrained
_max = 0.76 e Å^-3
_min = -0.49 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO3ⁱ	0.88	2.01	2.854 (4)	160
N4-H4AO1	0.88	2.04	2.896 (3)	165
C7-H7O3ⁱ	0.95	2.49	3.261 (4)	139
C9-H9ABr2ⁱⁱ	0.98	2.89	3.697 (3)	141
C18-H18CN1ⁱⁱⁱ	0.98	2.60	3.548 (5)	162
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2632 ).

Acknowledgements

The authors acknowledge financial support from Zhejiang Police College, China.

References

Borg, S., Vollinga, R. C., Labarre, M., Payza, K., Terenius, L. & Luthman, K. (1999). J. Med. Chem. 42, 4331-4342.
Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cheng, X.-W. (2008). Acta Cryst. E64, o1396.
Hadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, J. (1987). Tetrahedron, 43, 1345-1360.
Parashar, R. K., Sharma, R. C., Kumar, A. & Mohanm, G. (1988). Inorg. Chim. Acta, 151, 201-208.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds