{2,2'-[(Benzyl-aza-nedi-yl)dimethylene]diphenolato}(methano-lato)boron.

The title compound, C(22)H(22)BNO(3), was unintentionally obtained from salicyl-aldehyde benzyl-amine 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 inter-molecular C-H⋯O hydrogen bonds link the mol-ecules 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 = 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

Δρmax = 0.23 e Å−3

Δρmin = −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.

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

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

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

C22H22BNO3	F(000) = 760
Mr = 359.22	Dx = 1.267 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.5041 (14) Å	Cell parameters from 2910 reflections
b = 10.6029 (12) Å	θ = 2.4–23.2°
c = 17.1420 (14) Å	µ = 0.08 mm−1
β = 124.054 (5)°	T = 273 K
V = 1882.9 (3) Å3	Block, colourless
Z = 4	0.31 × 0.26 × 0.22 mm

Bruker SMART APEX diffractometer	4540 independent reflections
Radiation source: fine-focus sealed tube	2558 reflections with I > 2σ(I)
graphite	Rint = 0.154
φ and ω scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
Tmin = 0.975, Tmax = 0.982	k = −13→14
11689 measured reflections	l = −19→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-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 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
B1	0.2232 (2)	0.32181 (19)	0.40625 (14)	0.0467 (5)
N2	0.20528 (12)	0.47562 (12)	0.39796 (8)	0.0405 (3)
O3	0.11650 (13)	0.26732 (11)	0.40506 (9)	0.0542 (3)
O4	0.34523 (13)	0.29948 (12)	0.49191 (9)	0.0613 (4)
O5	0.21491 (12)	0.28152 (10)	0.32141 (8)	0.0498 (3)
C6	0.31610 (16)	0.53161 (17)	0.39892 (12)	0.0487 (4)
H6A	0.3922	0.5319	0.4630	0.058*
H6B	0.2959	0.6184	0.3776	0.058*
C7	0.34535 (16)	0.45969 (17)	0.33689 (12)	0.0473 (4)
C8	0.29429 (17)	0.34032 (18)	0.30145 (12)	0.0488 (4)
C9	0.3203 (2)	0.27914 (19)	0.24196 (14)	0.0623 (5)
H9	0.2839	0.2008	0.2167	0.075*
C10	0.4007 (2)	0.3356 (2)	0.22079 (16)	0.0734 (6)
H10	0.4182	0.2947	0.1811	0.088*
C11	0.4551 (2)	0.4515 (2)	0.25773 (15)	0.0704 (6)
H11	0.5105	0.4880	0.2442	0.085*
C12	0.42708 (19)	0.51334 (19)	0.31478 (14)	0.0574 (5)
H12	0.4632	0.5922	0.3390	0.069*
C13	0.20248 (18)	0.52595 (15)	0.47992 (11)	0.0475 (4)
H13A	0.1326	0.4849	0.4792	0.057*
H13B	0.2825	0.5025	0.5382	0.057*
C14	0.18550 (18)	0.66690 (17)	0.48009 (11)	0.0481 (4)
C15	0.2926 (2)	0.74533 (18)	0.52878 (14)	0.0606 (5)
H15	0.3750	0.7106	0.5607	0.073*
C16	0.2782 (3)	0.8744 (2)	0.53036 (17)	0.0793 (7)
H16	0.3508	0.9256	0.5632	0.095*
C17	0.1563 (3)	0.9279 (2)	0.48346 (17)	0.0815 (7)
H17	0.1467	1.0148	0.4836	0.098*
C18	0.0494 (3)	0.8508 (2)	0.43666 (15)	0.0761 (7)
H18	−0.0328	0.8858	0.4059	0.091*
C19	0.0638 (2)	0.7210 (2)	0.43516 (14)	0.0626 (6)
H19	−0.0090	0.6698	0.4037	0.075*
C20	0.08093 (15)	0.50238 (15)	0.30599 (11)	0.0416 (4)
H20A	0.0898	0.4816	0.2548	0.050*
H20B	0.0613	0.5916	0.3019	0.050*
C21	−0.02795 (16)	0.42715 (15)	0.29604 (11)	0.0429 (4)
C22	−0.15376 (18)	0.47161 (18)	0.23826 (13)	0.0558 (5)
H22	−0.1697	0.5459	0.2046	0.067*
C23	−0.2553 (2)	0.4070 (2)	0.23014 (16)	0.0703 (6)
H23	−0.3390	0.4377	0.1913	0.084*
C24	−0.2323 (2)	0.2971 (2)	0.27968 (17)	0.0719 (7)
H24	−0.3006	0.2543	0.2750	0.086*
C25	−0.1073 (2)	0.24931 (18)	0.33692 (15)	0.0598 (5)
H25	−0.0925	0.1742	0.3696	0.072*
C26	−0.00545 (18)	0.31408 (16)	0.34496 (12)	0.0457 (4)
C27	0.4118 (2)	0.18849 (19)	0.50173 (16)	0.0716 (6)
H27A	0.3651	0.1176	0.5031	0.107*
H27B	0.4961	0.1915	0.5593	0.107*
H27C	0.4199	0.1800	0.4495	0.107*

	U11	U22	U33	U12	U13	U23
B1	0.0461 (12)	0.0474 (11)	0.0464 (11)	0.0016 (9)	0.0258 (10)	0.0020 (8)
N2	0.0369 (8)	0.0476 (8)	0.0388 (7)	−0.0015 (6)	0.0222 (7)	0.0012 (6)
O3	0.0582 (8)	0.0479 (7)	0.0628 (8)	−0.0006 (6)	0.0378 (7)	0.0096 (6)
O4	0.0543 (8)	0.0651 (8)	0.0502 (8)	0.0158 (7)	0.0206 (7)	0.0049 (6)
O5	0.0488 (7)	0.0512 (7)	0.0520 (7)	−0.0032 (6)	0.0299 (7)	−0.0048 (5)
C6	0.0384 (9)	0.0544 (10)	0.0531 (10)	−0.0058 (8)	0.0255 (9)	−0.0022 (8)
C7	0.0369 (9)	0.0574 (11)	0.0482 (10)	0.0032 (8)	0.0242 (8)	0.0059 (8)
C8	0.0426 (10)	0.0573 (11)	0.0467 (10)	0.0070 (9)	0.0250 (9)	0.0051 (8)
C9	0.0661 (13)	0.0670 (13)	0.0611 (13)	0.0116 (11)	0.0401 (12)	0.0007 (10)
C10	0.0798 (16)	0.0905 (16)	0.0720 (14)	0.0220 (14)	0.0561 (14)	0.0102 (12)
C11	0.0619 (13)	0.0920 (16)	0.0760 (14)	0.0161 (13)	0.0500 (12)	0.0216 (13)
C12	0.0461 (10)	0.0665 (12)	0.0632 (12)	0.0048 (10)	0.0328 (10)	0.0104 (10)
C13	0.0478 (10)	0.0552 (10)	0.0413 (9)	−0.0022 (8)	0.0260 (8)	−0.0008 (7)
C14	0.0531 (11)	0.0531 (10)	0.0394 (9)	0.0005 (9)	0.0267 (9)	−0.0028 (8)
C15	0.0637 (13)	0.0605 (12)	0.0525 (12)	−0.0071 (11)	0.0293 (11)	−0.0051 (9)
C16	0.1020 (19)	0.0619 (14)	0.0735 (15)	−0.0152 (14)	0.0489 (15)	−0.0104 (11)
C17	0.122 (2)	0.0552 (12)	0.0719 (15)	0.0098 (16)	0.0575 (16)	0.0010 (11)
C18	0.0910 (17)	0.0770 (15)	0.0596 (13)	0.0318 (15)	0.0417 (13)	0.0044 (11)
C19	0.0575 (12)	0.0742 (14)	0.0526 (12)	0.0079 (11)	0.0287 (11)	−0.0077 (10)
C20	0.0381 (9)	0.0464 (9)	0.0410 (9)	0.0011 (7)	0.0226 (8)	0.0029 (7)
C21	0.0409 (9)	0.0472 (9)	0.0427 (9)	−0.0056 (8)	0.0247 (8)	−0.0069 (7)
C22	0.0429 (10)	0.0646 (12)	0.0541 (11)	−0.0019 (9)	0.0236 (9)	−0.0065 (9)
C23	0.0416 (11)	0.0870 (16)	0.0757 (14)	−0.0103 (11)	0.0288 (11)	−0.0199 (12)
C24	0.0570 (14)	0.0882 (17)	0.0850 (16)	−0.0296 (12)	0.0487 (13)	−0.0329 (13)
C25	0.0733 (14)	0.0550 (11)	0.0709 (14)	−0.0205 (11)	0.0524 (13)	−0.0153 (9)
C26	0.0474 (10)	0.0471 (10)	0.0495 (10)	−0.0072 (8)	0.0314 (9)	−0.0081 (8)
C27	0.0639 (14)	0.0677 (13)	0.0718 (14)	0.0189 (11)	0.0309 (13)	0.0179 (10)

B1—O4	1.425 (2)	C14—C15	1.389 (3)
B1—O3	1.443 (2)	C15—C16	1.382 (3)
B1—O5	1.463 (2)	C15—H15	0.9300
B1—N2	1.641 (2)	C16—C17	1.385 (3)
N2—C20	1.4962 (19)	C16—H16	0.9300
N2—C6	1.499 (2)	C17—C18	1.377 (3)
N2—C13	1.521 (2)	C17—H17	0.9300
O3—C26	1.369 (2)	C18—C19	1.390 (3)
O4—C27	1.396 (2)	C18—H18	0.9300
O5—C8	1.368 (2)	C19—H19	0.9300
C6—C7	1.510 (2)	C20—C21	1.503 (2)
C6—H6A	0.9700	C20—H20A	0.9700
C6—H6B	0.9700	C20—H20B	0.9700
C7—C12	1.395 (2)	C21—C22	1.390 (3)
C7—C8	1.394 (3)	C21—C26	1.398 (2)
C8—C9	1.392 (3)	C22—C23	1.379 (3)
C9—C10	1.381 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.374 (3)
C10—C11	1.376 (3)	C23—H23	0.9300
C10—H10	0.9300	C24—C25	1.394 (3)
C11—C12	1.375 (3)	C24—H24	0.9300
C11—H11	0.9300	C25—C26	1.385 (3)
C12—H12	0.9300	C25—H25	0.9300
C13—C14	1.510 (2)	C27—H27A	0.9600
C13—H13A	0.9700	C27—H27B	0.9600
C13—H13B	0.9700	C27—H27C	0.9600
C14—C19	1.388 (3)
O4—B1—O3	113.34 (15)	C15—C14—C13	120.28 (17)
O4—B1—O5	114.47 (16)	C16—C15—C14	120.7 (2)
O3—B1—O5	108.60 (15)	C16—C15—H15	119.6
O4—B1—N2	105.64 (14)	C14—C15—H15	119.6
O3—B1—N2	108.45 (14)	C15—C16—C17	120.5 (2)
O5—B1—N2	105.89 (13)	C15—C16—H16	119.7
C20—N2—C6	110.19 (12)	C17—C16—H16	119.7
C20—N2—C13	111.03 (13)	C18—C17—C16	119.2 (2)
C6—N2—C13	110.50 (13)	C18—C17—H17	120.4
C20—N2—B1	106.88 (12)	C16—C17—H17	120.4
C6—N2—B1	108.19 (13)	C17—C18—C19	120.3 (2)
C13—N2—B1	109.94 (12)	C17—C18—H18	119.8
C26—O3—B1	119.80 (13)	C19—C18—H18	119.8
C27—O4—B1	119.10 (15)	C14—C19—C18	120.8 (2)
C8—O5—B1	117.29 (14)	C14—C19—H19	119.6
N2—C6—C7	112.28 (14)	C18—C19—H19	119.6
N2—C6—H6A	109.1	N2—C20—C21	111.08 (12)
C7—C6—H6A	109.1	N2—C20—H20A	109.4
N2—C6—H6B	109.1	C21—C20—H20A	109.4
C7—C6—H6B	109.1	N2—C20—H20B	109.4
H6A—C6—H6B	107.9	C21—C20—H20B	109.4
C12—C7—C8	118.56 (17)	H20A—C20—H20B	108.0
C12—C7—C6	119.24 (17)	C22—C21—C26	119.04 (17)
C8—C7—C6	122.19 (16)	C22—C21—C20	119.51 (15)
O5—C8—C9	118.10 (17)	C26—C21—C20	121.44 (15)
O5—C8—C7	121.60 (15)	C23—C22—C21	120.91 (19)
C9—C8—C7	120.28 (18)	C23—C22—H22	119.5
C10—C9—C8	119.6 (2)	C21—C22—H22	119.5
C10—C9—H9	120.2	C24—C23—C22	119.8 (2)
C8—C9—H9	120.2	C24—C23—H23	120.1
C11—C10—C9	120.7 (2)	C22—C23—H23	120.1
C11—C10—H10	119.6	C23—C24—C25	120.5 (2)
C9—C10—H10	119.6	C23—C24—H24	119.7
C12—C11—C10	119.7 (2)	C25—C24—H24	119.7
C12—C11—H11	120.1	C26—C25—C24	119.70 (19)
C10—C11—H11	120.1	C26—C25—H25	120.2
C11—C12—C7	121.0 (2)	C24—C25—H25	120.2
C11—C12—H12	119.5	O3—C26—C25	118.06 (16)
C7—C12—H12	119.5	O3—C26—C21	121.82 (16)
C14—C13—N2	115.15 (13)	C25—C26—C21	120.04 (18)
C14—C13—H13A	108.5	O4—C27—H27A	109.5
N2—C13—H13A	108.5	O4—C27—H27B	109.5
C14—C13—H13B	108.5	H27A—C27—H27B	109.5
N2—C13—H13B	108.5	O4—C27—H27C	109.5
H13A—C13—H13B	107.5	H27A—C27—H27C	109.5
C19—C14—C15	118.36 (17)	H27B—C27—H27C	109.5
C19—C14—C13	121.31 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O5i	0.93	2.54	3.399 (2)	153

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

Symmetry code: (i) .