2-Methyl-2,4-di-4-pyridyl-2,3-dihydro-1H-1,5-benzodiazepine acetic acid solvate

Shi-Chao Wang; Qiu-Fei Hou; Shi-Mei Jiang

doi:10.1107/S1600536809049836

. 2009 Nov 25;65(Pt 12):o3213. doi: 10.1107/S1600536809049836

2-Methyl-2,4-di-4-pyridyl-2,3-dihydro-1H-1,5-benzodiazepine acetic acid solvate

Shi-Chao Wang ^a, Qiu-Fei Hou ^a, Shi-Mei Jiang ^a,^*

PMCID: PMC2971997 PMID: 21578921

Abstract

In the title compound, C₂₀H₁₈N₄·CH₃COOH, the benzene ring forms dihedral angles of 81.34 (11) and 54.32 (11)° with the two pyridine rings. In the crystal, intermolecular O—H⋯N hydrogen bonding links one 1,5-benzodiazepine molecule and one acetic acid solvent molecule into a dimer. These dimers, related by translation along the b axis, are further linked into chains via weak intermolecular N—H⋯N hydrogen bonds.

Related literature

For details of the synthesis and a related compound, see Hou et al. (2007 ▶). graphic file with name e-65-o3213-scheme1.jpg

Experimental

Crystal data

C₂₀H₁₈N₄·C₂H₄O₂
M _r = 374.44
Triclinic,
a = 8.925 (6) Å
b = 10.172 (8) Å
c = 12.283 (9) Å
α = 68.56 (3)°
β = 75.41 (3)°
γ = 88.52 (3)°
V = 1001.8 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 K
0.11 × 0.10 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.991, T _max = 0.993
9946 measured reflections
4547 independent reflections
2400 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.211
S = 1.04
4547 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049836/cv2662sup1.cif

e-65-o3213-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049836/cv2662Isup2.hkl

e-65-o3213-Isup2.hkl^{(222.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N4ⁱ	0.86	2.23	3.079 (4)	172
O2—H2B⋯N3ⁱⁱ	0.82	1.83	2.640 (4)	168

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 20874038) and the National Basic Research Program of China (grant No. 2007CB936402).

supplementary crystallographic information

Comment

The title compound (I) was unexpectedly obtained during our study of the Schiff base bis-pyridine complex (Hou et al., 2007). In this paper, we report its crystal structure.

In (I) (Fig.1), the dihedral angles between benzene ring and two pyridine rings are 81.34 (11) ° and 54.32 (11) °, respectively. In the crystal structure, the intramolecular O—H···N and intermolecule N—H···N hydrogen bonds (Table 1) are observed.

Experimental

The title compound and its single crystals suitable for the X-ray diffraction were prepared by slow evaporation of the ethanol solution which contains o-phenylenediamine, 4-acetylpyridine and a small amount of acetic acid at room temperatue.