organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aRadiochemistry Laboratory, School of Nuclear Science and Technology, Lanzhou University, Lanzhou 730000, People's Republic of China
*Correspondence e-mail: klsz79@163.com

(Received 21 April 2011; accepted 5 May 2011; online 11 May 2011)

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[Muller, E. & Burgi, H. B. (1987). Helv. Chim. Acta, 70, 511-519.]).

[Scheme 1]

Experimental

Crystal data
  • C22H22BNO3

  • Mr = 359.22

  • Monoclinic, P 21 /c

  • 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[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. ]) Tmin = 0.975, Tmax = 0.982

  • 11689 measured reflections

  • 4540 independent reflections

  • 2558 reflections with I > 2σ(I)

  • Rint = 0.154

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.161

  • S = 1.01

  • 4540 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C22—H22⋯O5i 0.93 2.54 3.399 (2) 153
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. ]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. ]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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].

Related literature top

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

Experimental top

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.

Refinement top

H atoms were geometrically positioned (C—H 0.93-0.97 Å) and refined as riding, with Uiso(H) = 1.2-1.5 Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound showing the atomic numbering and 30% probability displacement ellipsoids. H-atoms omitted for clarity.
{2,2'-[(Benzylazanediyl)dimethylene]diphenolato}(methanolato)boron top
Crystal data top
C22H22BNO3F(000) = 760
Mr = 359.22Dx = 1.267 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.5041 (14) ÅCell parameters from 2910 reflections
b = 10.6029 (12) Åθ = 2.4–23.2°
c = 17.1420 (14) ŵ = 0.08 mm1
β = 124.054 (5)°T = 273 K
V = 1882.9 (3) Å3Block, colourless
Z = 40.31 × 0.26 × 0.22 mm
Data collection top
Bruker SMART APEX
diffractometer
4540 independent reflections
Radiation source: fine-focus sealed tube2558 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.154
ϕ and ω scansθmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1616
Tmin = 0.975, Tmax = 0.982k = 1314
11689 measured reflectionsl = 1922
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
4540 reflections(Δ/σ)max = 0.003
245 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C22H22BNO3V = 1882.9 (3) Å3
Mr = 359.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.5041 (14) ŵ = 0.08 mm1
b = 10.6029 (12) ÅT = 273 K
c = 17.1420 (14) Å0.31 × 0.26 × 0.22 mm
β = 124.054 (5)°
Data collection top
Bruker SMART APEX
diffractometer
4540 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2558 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.982Rint = 0.154
11689 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.161H-atom parameters constrained
S = 1.01Δρmax = 0.23 e Å3
4540 reflectionsΔρmin = 0.24 e Å3
245 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
B10.2232 (2)0.32181 (19)0.40625 (14)0.0467 (5)
N20.20528 (12)0.47562 (12)0.39796 (8)0.0405 (3)
O30.11650 (13)0.26732 (11)0.40506 (9)0.0542 (3)
O40.34523 (13)0.29948 (12)0.49191 (9)0.0613 (4)
O50.21491 (12)0.28152 (10)0.32141 (8)0.0498 (3)
C60.31610 (16)0.53161 (17)0.39892 (12)0.0487 (4)
H6A0.39220.53190.46300.058*
H6B0.29590.61840.37760.058*
C70.34535 (16)0.45969 (17)0.33689 (12)0.0473 (4)
C80.29429 (17)0.34032 (18)0.30145 (12)0.0488 (4)
C90.3203 (2)0.27914 (19)0.24196 (14)0.0623 (5)
H90.28390.20080.21670.075*
C100.4007 (2)0.3356 (2)0.22079 (16)0.0734 (6)
H100.41820.29470.18110.088*
C110.4551 (2)0.4515 (2)0.25773 (15)0.0704 (6)
H110.51050.48800.24420.085*
C120.42708 (19)0.51334 (19)0.31478 (14)0.0574 (5)
H120.46320.59220.33900.069*
C130.20248 (18)0.52595 (15)0.47992 (11)0.0475 (4)
H13A0.13260.48490.47920.057*
H13B0.28250.50250.53820.057*
C140.18550 (18)0.66690 (17)0.48009 (11)0.0481 (4)
C150.2926 (2)0.74533 (18)0.52878 (14)0.0606 (5)
H150.37500.71060.56070.073*
C160.2782 (3)0.8744 (2)0.53036 (17)0.0793 (7)
H160.35080.92560.56320.095*
C170.1563 (3)0.9279 (2)0.48346 (17)0.0815 (7)
H170.14671.01480.48360.098*
C180.0494 (3)0.8508 (2)0.43666 (15)0.0761 (7)
H180.03280.88580.40590.091*
C190.0638 (2)0.7210 (2)0.43516 (14)0.0626 (6)
H190.00900.66980.40370.075*
C200.08093 (15)0.50238 (15)0.30599 (11)0.0416 (4)
H20A0.08980.48160.25480.050*
H20B0.06130.59160.30190.050*
C210.02795 (16)0.42715 (15)0.29604 (11)0.0429 (4)
C220.15376 (18)0.47161 (18)0.23826 (13)0.0558 (5)
H220.16970.54590.20460.067*
C230.2553 (2)0.4070 (2)0.23014 (16)0.0703 (6)
H230.33900.43770.19130.084*
C240.2323 (2)0.2971 (2)0.27968 (17)0.0719 (7)
H240.30060.25430.27500.086*
C250.1073 (2)0.24931 (18)0.33692 (15)0.0598 (5)
H250.09250.17420.36960.072*
C260.00545 (18)0.31408 (16)0.34496 (12)0.0457 (4)
C270.4118 (2)0.18849 (19)0.50173 (16)0.0716 (6)
H27A0.36510.11760.50310.107*
H27B0.49610.19150.55930.107*
H27C0.41990.18000.44950.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0461 (12)0.0474 (11)0.0464 (11)0.0016 (9)0.0258 (10)0.0020 (8)
N20.0369 (8)0.0476 (8)0.0388 (7)0.0015 (6)0.0222 (7)0.0012 (6)
O30.0582 (8)0.0479 (7)0.0628 (8)0.0006 (6)0.0378 (7)0.0096 (6)
O40.0543 (8)0.0651 (8)0.0502 (8)0.0158 (7)0.0206 (7)0.0049 (6)
O50.0488 (7)0.0512 (7)0.0520 (7)0.0032 (6)0.0299 (7)0.0048 (5)
C60.0384 (9)0.0544 (10)0.0531 (10)0.0058 (8)0.0255 (9)0.0022 (8)
C70.0369 (9)0.0574 (11)0.0482 (10)0.0032 (8)0.0242 (8)0.0059 (8)
C80.0426 (10)0.0573 (11)0.0467 (10)0.0070 (9)0.0250 (9)0.0051 (8)
C90.0661 (13)0.0670 (13)0.0611 (13)0.0116 (11)0.0401 (12)0.0007 (10)
C100.0798 (16)0.0905 (16)0.0720 (14)0.0220 (14)0.0561 (14)0.0102 (12)
C110.0619 (13)0.0920 (16)0.0760 (14)0.0161 (13)0.0500 (12)0.0216 (13)
C120.0461 (10)0.0665 (12)0.0632 (12)0.0048 (10)0.0328 (10)0.0104 (10)
C130.0478 (10)0.0552 (10)0.0413 (9)0.0022 (8)0.0260 (8)0.0008 (7)
C140.0531 (11)0.0531 (10)0.0394 (9)0.0005 (9)0.0267 (9)0.0028 (8)
C150.0637 (13)0.0605 (12)0.0525 (12)0.0071 (11)0.0293 (11)0.0051 (9)
C160.1020 (19)0.0619 (14)0.0735 (15)0.0152 (14)0.0489 (15)0.0104 (11)
C170.122 (2)0.0552 (12)0.0719 (15)0.0098 (16)0.0575 (16)0.0010 (11)
C180.0910 (17)0.0770 (15)0.0596 (13)0.0318 (15)0.0417 (13)0.0044 (11)
C190.0575 (12)0.0742 (14)0.0526 (12)0.0079 (11)0.0287 (11)0.0077 (10)
C200.0381 (9)0.0464 (9)0.0410 (9)0.0011 (7)0.0226 (8)0.0029 (7)
C210.0409 (9)0.0472 (9)0.0427 (9)0.0056 (8)0.0247 (8)0.0069 (7)
C220.0429 (10)0.0646 (12)0.0541 (11)0.0019 (9)0.0236 (9)0.0065 (9)
C230.0416 (11)0.0870 (16)0.0757 (14)0.0103 (11)0.0288 (11)0.0199 (12)
C240.0570 (14)0.0882 (17)0.0850 (16)0.0296 (12)0.0487 (13)0.0329 (13)
C250.0733 (14)0.0550 (11)0.0709 (14)0.0205 (11)0.0524 (13)0.0153 (9)
C260.0474 (10)0.0471 (10)0.0495 (10)0.0072 (8)0.0314 (9)0.0081 (8)
C270.0639 (14)0.0677 (13)0.0718 (14)0.0189 (11)0.0309 (13)0.0179 (10)
Geometric parameters (Å, º) top
B1—O41.425 (2)C14—C151.389 (3)
B1—O31.443 (2)C15—C161.382 (3)
B1—O51.463 (2)C15—H150.9300
B1—N21.641 (2)C16—C171.385 (3)
N2—C201.4962 (19)C16—H160.9300
N2—C61.499 (2)C17—C181.377 (3)
N2—C131.521 (2)C17—H170.9300
O3—C261.369 (2)C18—C191.390 (3)
O4—C271.396 (2)C18—H180.9300
O5—C81.368 (2)C19—H190.9300
C6—C71.510 (2)C20—C211.503 (2)
C6—H6A0.9700C20—H20A0.9700
C6—H6B0.9700C20—H20B0.9700
C7—C121.395 (2)C21—C221.390 (3)
C7—C81.394 (3)C21—C261.398 (2)
C8—C91.392 (3)C22—C231.379 (3)
C9—C101.381 (3)C22—H220.9300
C9—H90.9300C23—C241.374 (3)
C10—C111.376 (3)C23—H230.9300
C10—H100.9300C24—C251.394 (3)
C11—C121.375 (3)C24—H240.9300
C11—H110.9300C25—C261.385 (3)
C12—H120.9300C25—H250.9300
C13—C141.510 (2)C27—H27A0.9600
C13—H13A0.9700C27—H27B0.9600
C13—H13B0.9700C27—H27C0.9600
C14—C191.388 (3)
O4—B1—O3113.34 (15)C15—C14—C13120.28 (17)
O4—B1—O5114.47 (16)C16—C15—C14120.7 (2)
O3—B1—O5108.60 (15)C16—C15—H15119.6
O4—B1—N2105.64 (14)C14—C15—H15119.6
O3—B1—N2108.45 (14)C15—C16—C17120.5 (2)
O5—B1—N2105.89 (13)C15—C16—H16119.7
C20—N2—C6110.19 (12)C17—C16—H16119.7
C20—N2—C13111.03 (13)C18—C17—C16119.2 (2)
C6—N2—C13110.50 (13)C18—C17—H17120.4
C20—N2—B1106.88 (12)C16—C17—H17120.4
C6—N2—B1108.19 (13)C17—C18—C19120.3 (2)
C13—N2—B1109.94 (12)C17—C18—H18119.8
C26—O3—B1119.80 (13)C19—C18—H18119.8
C27—O4—B1119.10 (15)C14—C19—C18120.8 (2)
C8—O5—B1117.29 (14)C14—C19—H19119.6
N2—C6—C7112.28 (14)C18—C19—H19119.6
N2—C6—H6A109.1N2—C20—C21111.08 (12)
C7—C6—H6A109.1N2—C20—H20A109.4
N2—C6—H6B109.1C21—C20—H20A109.4
C7—C6—H6B109.1N2—C20—H20B109.4
H6A—C6—H6B107.9C21—C20—H20B109.4
C12—C7—C8118.56 (17)H20A—C20—H20B108.0
C12—C7—C6119.24 (17)C22—C21—C26119.04 (17)
C8—C7—C6122.19 (16)C22—C21—C20119.51 (15)
O5—C8—C9118.10 (17)C26—C21—C20121.44 (15)
O5—C8—C7121.60 (15)C23—C22—C21120.91 (19)
C9—C8—C7120.28 (18)C23—C22—H22119.5
C10—C9—C8119.6 (2)C21—C22—H22119.5
C10—C9—H9120.2C24—C23—C22119.8 (2)
C8—C9—H9120.2C24—C23—H23120.1
C11—C10—C9120.7 (2)C22—C23—H23120.1
C11—C10—H10119.6C23—C24—C25120.5 (2)
C9—C10—H10119.6C23—C24—H24119.7
C12—C11—C10119.7 (2)C25—C24—H24119.7
C12—C11—H11120.1C26—C25—C24119.70 (19)
C10—C11—H11120.1C26—C25—H25120.2
C11—C12—C7121.0 (2)C24—C25—H25120.2
C11—C12—H12119.5O3—C26—C25118.06 (16)
C7—C12—H12119.5O3—C26—C21121.82 (16)
C14—C13—N2115.15 (13)C25—C26—C21120.04 (18)
C14—C13—H13A108.5O4—C27—H27A109.5
N2—C13—H13A108.5O4—C27—H27B109.5
C14—C13—H13B108.5H27A—C27—H27B109.5
N2—C13—H13B108.5O4—C27—H27C109.5
H13A—C13—H13B107.5H27A—C27—H27C109.5
C19—C14—C15118.36 (17)H27B—C27—H27C109.5
C19—C14—C13121.31 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O5i0.932.543.399 (2)153
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC22H22BNO3
Mr359.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)12.5041 (14), 10.6029 (12), 17.1420 (14)
β (°) 124.054 (5)
V3)1882.9 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.31 × 0.26 × 0.22
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.975, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
11689, 4540, 2558
Rint0.154
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.161, 1.01
No. of reflections4540
No. of parameters245
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.24

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O5i0.932.543.399 (2)152.9
Symmetry code: (i) x, y+1/2, z+1/2.
 

Acknowledgements

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

References

First citationBruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMuller, E. & Burgi, H. B. (1987). Helv. Chim. Acta, 70, 511–519.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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