{2,2′-[(Benzyl­aza­nedi­yl)dimethylene]diphenolato}(methano­lato)boron

Yanxia Geng; Wangsuo Wu

doi:10.1107/S1600536811016990

. 2011 May 11;67(Pt 6):o1380. doi: 10.1107/S1600536811016990

{2,2′-[(Benzylazanediyl)dimethylene]diphenolato}(methanolato)boron

Yanxia Geng ^a, Wangsuo Wu ^a,^*

PMCID: PMC3120563 PMID: 21754770

Abstract

The title compound, C₂₂H₂₂BNO₃, was unintentionally obtained from salicylaldehyde benzylamine and sodium borohydride. The B—O bond lengths lie in the range 1.425 (2)–1.463 (2) Å, and B—N = 1.641 (2) Å. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into chains in the [010] direction.

Related literature

For the crystal structure of a related compound, see: Muller & Burgi (1987 ▶).

Experimental

Crystal data

C₂₂H₂₂BNO₃
M _r = 359.22
Monoclinic,
a = 12.5041 (14) Å
b = 10.6029 (12) Å
c = 17.1420 (14) Å
β = 124.054 (5)°
V = 1882.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 K
0.31 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.975, T _max = 0.982
11689 measured reflections
4540 independent reflections
2558 reflections with I > 2σ(I)
R _int = 0.154

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.161
S = 1.01
4540 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016990/cv5081sup1.cif

e-67-o1380-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016990/cv5081Isup2.hkl

e-67-o1380-Isup2.hkl^{(222.4KB, 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
C22—H22⋯O5ⁱ	0.93	2.54	3.399 (2)	153

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the National Natural Science Foundation support of China (Nos. 20871062 and J1030932).

supplementary crystallographic information

Comment

The title compound, (I), has been unintentionally obtained during the attempts to synthesize the metal complexes with phenolamine derivatives.

In (I), all bond lengths and angles are normal and comparable with those observed in 2,2',2''-nitrilotriphenyl borate(III) (Muller & Burgi, 1987). The B1—N2 bond of 1.642 (2) Å indicates strong contact due to the electric charge action. Weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains in [010].

Experimental

The salicylaldehyde (4.4 ml, 0.04 mol) was disolved in 25 ml anhydrous methanol, then benzylamine 4.4 ml(0. 04 mol) disolved in 15 ml anhydrous methnol was added to the former by drops.After reacted under ultrasonography for 40 min, sodium borohydride (1.5 g, 0.04 mol) were added in batch. After reacted under ultrasonography for another 20 min, 1, 4-dibromo-butane(2.4 ml, 0.02 mol) were added, After stirring of 24 h at room temperature. The precipitate was filtered off and dried. The single-crystal suitable for X-ray diffraction analysis was obtained by recrystallization from methanol.

The yield is 75% and elemental analysis: calc. for C₂₂H₂₂BNO₃: C 73.55, H 6.17, N 3.90; found: C 72.81, H 6.49, N 3.53. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.