(IUCr) N-{3-[Bis(2-hydroxyethyl)aminomethyl]-5-nitrophenyl}benzamide

Volume 64
Part 6
Pages o978-o979
June 2008

Received 11 March 2008
Accepted 6 April 2008
Online 3 May 2008

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.003 Å
R = 0.059
wR = 0.134
Data-to-parameter ratio = 14.3
Details

N-{3-[Bis(2-hydroxyethyl)aminomethyl]-5-nitrophenyl}benzamide

Anna Mai,^a Gul S. Khan,^a George R. Clark ^a and David Barker ^a ^*

^aDepartment of Chemistry, The University of Auckland, Private Bag 92019, Auckland, New Zealand
Correspondence e-mail: g.clark@auckland.ac.nz

The title compound, C₁₈H₂₁N₃O₅, was prepared by the reaction of 3-benzamido-5-nitrobenzyl methanesulfonate with diethanolamine and is an intermediate in the synthesis of DNA minor-groove-binding polybenzamide agents capable of being conjugated to additional biologically active species. The asymmetric unit contains two independent molecules, which differ only in the orientations of the hydroxyethyl groups. In the crystal structure, intermolecular N-HO and O-HO hydrogen bonds link molecules into one-dimensional chains.

Related literature

For related literature on the biological activity of polybenzamide DNA binding agents, see: Storl et al. (1993). For related literature on natural and synthetic minor-groove binding agents, including agents containing conjugates, see: Arcamone et al. (1964); Atwell et al. (1995); Baraldi et al. (1999, 2004, 2007); Kumar et al. (2004); Sengupta et al. (1996); Stafford et al. (2007); Turner et al. (1999); Wemmer (2000); Yan et al. (1997). For related literature, see: Barker et al. (2008).

Experimental

Crystal data

C₁₈H₂₁N₃O₅
M_r = 359.38
Monoclinic, P 2₁ /c
a = 22.7867 (3) Å
b = 11.0879 (1) Å
c = 13.5106 (1) Å
= 90.114 (1)°
V = 3413.54 (6) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 90 (2) K
0.34 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) T_min = 0.858, T_max = 0.978
20279 measured reflections
6944 independent reflections
5142 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.134
S = 1.04
6944 reflections
485 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4A-HO4AO1Aⁱ	0.93 (4)	1.82 (4)	2.736 (2)	168 (3)
O5A-HO5AO4B	0.89 (3)	1.85 (3)	2.738 (2)	178 (3)
N1A-H1AO5B	0.86	2.27	3.089 (2)	159
O5B-HO5BO4B	0.90 (4)	2.30 (4)	3.130 (3)	153 (3)
O4B-HO4BO4A	1.03 (4)	1.75 (4)	2.762 (3)	169 (3)
N1B-H1BO5A	0.86	2.49	3.332 (2)	167
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 1995); cell refinement: SAINT (Bruker, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2602 ).

Acknowledgements

The authors acknowledge financial support from the Higher Education Commission of Pakistan and the University of Auckland, New Zealand.

References

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organic compounds