4-(Piperidin-1-yl)-4H-benzo[b]tetra­zolo[1,5-d][1,4]diazepin-5(6H)-one

Nichol, G.S.; Xu, Z.; Kaiser, C.E.; Hulme, C.

doi:10.1107/S1600536810049950

Volume 67
Part 1
Pages o23-o24
January 2011

Received 15 November 2010
Accepted 29 November 2010
Online 4 December 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.043
wR = 0.123
Data-to-parameter ratio = 24.0
Details

4-(Piperidin-1-yl)-4H-benzo[b]tetrazolo[1,5-d][1,4]diazepin-5(6H)-one

Gary S. Nichol,^a ^* Zhigang Xu,^b Christine E. Kaiser ^b and Christopher Hulme ^b

^aDepartment of Chemistry and Biochemistry, 1306 E University Boulevard, The University of Arizona, Tucson, AZ 85721, USA, and ^bSouthwest Center for Drug, Discovery and Development, College of Pharmacy, BIO5 Institute, The University of Arizona, Tucson, AZ 85721, USA
Correspondence e-mail: gsnichol@email.arizona.edu

There are two crystallographically unique molecules present in the asymmetric unit of the title compound, C₁₄H₁₆N₆O; in both molecules, the seven-membered diazepinone ring adopts a boat-like conformation and the chair conformation piperidine ring is an axial substituent on the diazepinone ring. In the crystal, each molecule forms hydrogen bonds with its respective symmetry equivalents. Hydrogen bonding between molecule A and symmetry equivalents forms two ring motifs, the first formed by inversion-related N-HO interactions and the second formed by C-HO and C-HN interactions. The combination of both ring motifs results in the formation of an infinite double tape, which propagates in the a-axis direction. Hydrogen bonding between molecule B and symmetry equivalents forms one ring motif by inversion-related N-HO interactions and a second ring motif by C-HO interactions, which propagate as a single tape parallel with the c axis.

Related literature

The structure of the title compound was determined as part of a larger study on development of synthetic methods for high-throughput medicinal chemistry. For background to the use of multi-component reactions in high-throughput medicinal chemistry, see: Gunawan et al. (2010); Hulme & Dietrich (2009); Hulme & Gore (2003). For the Ugi reaction, see: Ugi & Steinbrückner (1961). For graph-set notation for hydrogen bonding, see: Bernstein et al. (1995) and puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₄H₁₆N₆O
M_r = 284.33
Triclinic, $[P \overline 1]$
a = 8.8210 (7) Å
b = 13.1802 (10) Å
c = 13.4476 (11) Å
= 105.549 (2)°
= 99.490 (2)°
= 106.623 (2)°
V = 1392.99 (19) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.39 × 0.28 × 0.09 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: numerical (SADABS; Sheldrick, 1996) T_min = 0.965, T_max = 0.992
51078 measured reflections
12177 independent reflections
9733 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.123
S = 1.05
12177 reflections
507 parameters
All H-atom parameters refined
_max = 0.59 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.850 (14)	2.069 (14)	2.9089 (9)	169.4 (13)
N51-H51NO51ⁱⁱ	0.886 (16)	1.929 (16)	2.8116 (10)	173.6 (14)
C6-H6N2ⁱⁱⁱ	0.936 (15)	2.531 (15)	3.4638 (11)	174.8 (12)
C7-H7O1ⁱⁱⁱ	0.947 (15)	2.406 (15)	3.3394 (10)	168.4 (13)
C55-H55N54^iv	0.974 (13)	2.548 (13)	3.2293 (11)	127.0 (10)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al. 2008); software used to prepare material for publication: SHELXTL and local programs.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2167 ).

Acknowledgements

The diffractometer was purchased with funding from NSF grant CHE-0741837.

References

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organic compounds