{2-Hydr­oxy-6-[(2-oxidophen­yl)imino­methyl-κ2N,O]phenolato-κO1}phenyl­boron

Vega, A.; Tlahuext, H.; Höpfl, H.

doi:10.1107/S1600536810007609

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o758

doi:10.1107/S1600536810007609

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{2-Hydroxy-6-[(2-oxidophenyl)iminomethyl-κ²N,O]phenolato-κO¹}phenylboron

Araceli Vega,^a Hugo Tlahuext ^a and Herbert Höpfl ^a ^*

^aCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Col. Chamilpa, CP 62209, Cuernavaca Mor., Mexico
^*Correspondence e-mail: hhopfl@uaem.mx

(Received 25 February 2010; accepted 28 February 2010; online 6 March 2010)

The [4.3.0]heterobicyclic title structure, C₁₉H₁₄BNO₃, is composed of a five-membered OBNC₂ ring and a six-membered OBNC₃ ring, each of which has an approximate envelope conformation. The coordination geometry of the B atom is distorted tetrahedral. In the crystal structure, centrosymmetrically related molecules are associated through pairs of O—H⋯O hydrogen bonds.

Related literature

For related boronates, see: Barba et al. (2001 ); Höpfl et al. (1998 ); Lamère et al. (2006 ). For boronates with non-linear optical properties, see: Reyes et al. (2005 ); Muñoz et al. (2008 ). For the use of boronates in organic synthesis, see: Rodríguez et al. (2005a ,b ); López-Ruiz et al. (2008 ). For a definition of the tetrahedral character in boron compounds, see: Höpfl et al. (1999 ).

Experimental

Crystal data

C₁₉H₁₄BNO₃
M_r = 315.12
Orthorhombic, P b c a
a = 14.7245 (13) Å
b = 11.196 (1) Å
c = 18.4060 (16) Å
V = 3034.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.21 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.985
31865 measured reflections
3317 independent reflections
1942 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.127
S = 1.09
3317 reflections
220 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3′⋯O2ⁱ	0.84 (2)	1.97 (2)	2.740 (2)	152 (3)
C7—H7⋯O3ⁱⁱ	0.93	2.53	3.165 (3)	126
Symmetry codes: (i) -x, -y+2, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus NT (Bruker, 2001 ); data reduction: SAINT-Plus NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007609/tk2636sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007609/tk2636Isup2.hkl

checkCIF report

Comment top

Recently, boronates derived from ligands having electron-donating and -attracting groups have been prepared in order to generate chromophores with nonlinear optical properties (Reyes et al., 2005; Lamère et al., 2006; Muñoz et al., 2008). Boronates derived from Schiff bases have been applied in Diels-Alder reactions and for the stereoselective addition of Grignard reagents to azomethine carbon atoms (Rodríguez et al., 2005a, 2005b; López-Ruiz et al., 2008).

We have synthesized the [4.3.0]heterobicycle (I), Fig. 1, which is composed of a five-membered OBNC₂ ring and a six-membered OBNC₃ ring. The N→B, B—O and B—C bond lengths are comparable to the values determined for the molecular structure of the boronate obtained from the unsubstituted ligand 2-[[(2-hydroxyphenyl)imino]methyl]phenol (Höpfl et al., 1998; Barba et al., 2001); however, the sum of bond lengths at the boron atom is significantly shorter for (I) (6.15 versus 6.18 Å), indicating that there is a small, but systematic tendency for bond length shortening.

The bond angles around the boron atom vary from 98.72 (2) ° for O2—B1—N1 to 112.8 (2) ° for O2—B1—C14, thus indicating a significant distortion from ideal tetrahedral geometry, which can be seen also from the value for the tetrahedral character [71 %] (Höpfl, 1999).

In the five-membered ring, the bond angles vary from 98.7 (2) to 114.0 (2) ° giving a mean value of 106.9 °. In the six-membered heterocycle, the bond angles range from 106.6 (2) to 123.4 (2) °, and the mean value is 117.9 °. Both rings have an approximate envelope conformation, in which the boron atom is localized at the tip. The proximity to an ideal envelope can be illustrated by the N1—C8—C9—O2 torsion angle [-2.7 (3) °] in the first case, and the O1—C1—C2—C7 and C2—C7—N1—B1 torsion angles [2.3 (3) and 2.5 (3) °] in the second case.

The degree of π–delocalization between the aromatic rings connected by the imino group can be analyzed by the C–N–C–C torsion angles (Reyes et al., 2005; Lamère et al., 2006; Muñoz et al., 2008). The C7—N1—C8—C13 torsion angle has a value of 26.1 (4) ° indicating that the π–delocalization is distorted. The distortion can be evidenced also by the relatively long N1—C7 bond [1.282 (3) Å].

In the crystal structure, neighboring molecules are associated through O3—H···O2ⁱ hydrogen bonds [symmetry code: (i), -x, 2-y, 1-z] to form supramolecular dimeric units having crystallographic inversion symmetry (Fig. 2). The crystal packing is further stabilized by C—H···O interactions (Table 1).

Related literature top

For related boronates, see: Barba et al. ( 2001); Höpfl et al. (1998); Lamère et al. (2006). For boronates with non-linear optical properties, see: Reyes et al. (2005); Muñoz et al. (2008). For the use of boronates in organic synthesis, see: Rodríguez et al. (2005a,b); López-Ruiz et al. (2008). For a definition of the tetrahedral character in boron compounds, see: Höpfl et al. (1999).

Experimental top

For the preparation of (I), 2,3-dihydroxysalicylaldehyde (0.250 g, 1.81 mmol), 2-aminophenol (0.198 g, 1.81 mmol) and phenylboronic acid (0.221 g, 1.81 mmol) were dissolved in DMF (35 ml), and the solution was refluxed for 1 h in the presence of a Dean-Stark trap. After cooling, the product precipitated in the form of a yellow crystalline solid, which was filtered and washed with hexane. Yield: 0.102 g (18 %). M.pt. 531 K.

MS (FAB⁺): m/z (%) = 316 ([M+H]⁺, 40).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus NT (Bruker, 2001); data reduction: SAINT-Plus NT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Perspective view of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Fragment of the crystal structure of (I), showing the supramolecular aggregate formed through O—H···O hydrogen bonding interactions. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

{2-Hydroxy-6-[(2-oxidophenyl)iminomethyl-κ²N,O]phenolato- κO¹}phenylboron top

Crystal data top

C₁₉H₁₄BNO₃	D_x = 1.380 Mg m⁻³
M_r = 315.12	Melting point: 531 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3128 reflections
a = 14.7245 (13) Å	θ = 2.2–21.4°
b = 11.196 (1) Å	µ = 0.09 mm⁻¹
c = 18.4060 (16) Å	T = 293 K
V = 3034.3 (5) Å³	Rectangular prism, orange
Z = 8	0.21 × 0.20 × 0.16 mm
F(000) = 1312

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3317 independent reflections
Radiation source: fine-focus sealed tube	1942 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.088
Detector resolution: 8.3 pixels mm^-1	θ_max = 27.0°, θ_min = 2.2°
phi and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
T_min = 0.981, T_max = 0.985	l = −23→23
31865 measured reflections

Refinement top

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0408P)² + 0.7703P] where P = (F_o² + 2F_c²)/3
3317 reflections	(Δ/σ)_max = 0.001
220 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₁₄BNO₃	V = 3034.3 (5) Å³
M_r = 315.12	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.7245 (13) Å	µ = 0.09 mm⁻¹
b = 11.196 (1) Å	T = 293 K
c = 18.4060 (16) Å	0.21 × 0.20 × 0.16 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3317 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1942 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.088
31865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	1 restraint
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.14 e Å⁻³
3317 reflections	Δρ_min = −0.19 e Å⁻³
220 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
B1	0.10076 (17)	0.8654 (3)	0.51225 (15)	0.0453 (7)
N1	0.20017 (12)	0.80938 (17)	0.50322 (10)	0.0460 (5)
O1	0.11329 (10)	0.98838 (14)	0.53706 (8)	0.0486 (4)
O2	0.07078 (10)	0.85831 (14)	0.43509 (8)	0.0514 (4)
O3	0.09544 (12)	1.17706 (17)	0.62833 (11)	0.0672 (6)
H3'	0.0545 (15)	1.147 (3)	0.6024 (14)	0.101*
C1	0.17986 (15)	1.0082 (2)	0.58667 (12)	0.0467 (6)
C2	0.25781 (16)	0.9374 (2)	0.59210 (13)	0.0479 (6)
C3	0.32673 (17)	0.9695 (2)	0.64063 (14)	0.0579 (7)
H3	0.3794	0.9238	0.6432	0.069*
C4	0.31745 (18)	1.0667 (3)	0.68403 (14)	0.0613 (7)
H4	0.3633	1.0874	0.7164	0.074*
C5	0.23854 (18)	1.1354 (2)	0.67962 (13)	0.0582 (7)
H5	0.2319	1.2017	0.7096	0.070*
C6	0.17066 (16)	1.1066 (2)	0.63186 (13)	0.0518 (6)
C7	0.26874 (16)	0.8426 (2)	0.54104 (13)	0.0506 (6)
H7	0.3248	0.8055	0.5353	0.061*
C8	0.19835 (16)	0.7394 (2)	0.43960 (12)	0.0466 (6)
C9	0.12224 (16)	0.7743 (2)	0.40089 (13)	0.0482 (6)
C10	0.10560 (18)	0.7249 (2)	0.33315 (14)	0.0576 (7)
H10	0.0555	0.7478	0.3057	0.069*
C11	0.1662 (2)	0.6406 (3)	0.30787 (14)	0.0622 (7)
H11	0.1565	0.6067	0.2624	0.075*
C12	0.24025 (19)	0.6050 (3)	0.34753 (14)	0.0619 (7)
H12	0.2788	0.5465	0.3291	0.074*
C13	0.25807 (17)	0.6548 (2)	0.41423 (14)	0.0565 (7)
H13	0.3086	0.6321	0.4412	0.068*
C14	0.03782 (15)	0.7892 (2)	0.56575 (12)	0.0444 (6)
C15	0.00739 (17)	0.6756 (2)	0.54791 (15)	0.0599 (7)
H15	0.0247	0.6426	0.5036	0.072*
C16	−0.04753 (19)	0.6099 (2)	0.59356 (17)	0.0707 (8)
H16	−0.0665	0.5338	0.5800	0.085*
C17	−0.07412 (18)	0.6570 (3)	0.65887 (16)	0.0649 (8)
H17	−0.1107	0.6128	0.6901	0.078*
C18	−0.04662 (17)	0.7693 (3)	0.67788 (14)	0.0590 (7)
H18	−0.0651	0.8021	0.7219	0.071*
C19	0.00840 (16)	0.8338 (2)	0.63199 (13)	0.0523 (6)
H19	0.0265	0.9100	0.6459	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0384 (14)	0.0458 (16)	0.0517 (17)	0.0035 (13)	−0.0048 (12)	−0.0004 (14)
N1	0.0408 (11)	0.0516 (12)	0.0455 (12)	−0.0010 (9)	0.0017 (9)	0.0026 (10)
O1	0.0430 (9)	0.0478 (10)	0.0551 (10)	−0.0032 (8)	−0.0085 (8)	0.0019 (8)
O2	0.0503 (10)	0.0558 (11)	0.0482 (10)	0.0042 (8)	−0.0050 (8)	0.0005 (8)
O3	0.0517 (11)	0.0594 (12)	0.0905 (15)	−0.0025 (10)	−0.0096 (10)	−0.0189 (10)
C1	0.0441 (14)	0.0494 (15)	0.0466 (14)	−0.0100 (12)	−0.0008 (12)	0.0056 (12)
C2	0.0442 (14)	0.0526 (15)	0.0469 (14)	−0.0062 (12)	−0.0031 (12)	0.0021 (12)
C3	0.0456 (15)	0.0660 (19)	0.0619 (17)	−0.0046 (13)	−0.0079 (13)	0.0010 (15)
C4	0.0540 (17)	0.0685 (19)	0.0614 (17)	−0.0169 (15)	−0.0099 (13)	0.0012 (15)
C5	0.0594 (17)	0.0547 (17)	0.0605 (17)	−0.0124 (14)	−0.0017 (14)	−0.0047 (14)
C6	0.0471 (15)	0.0507 (16)	0.0577 (16)	−0.0095 (12)	0.0020 (12)	0.0026 (13)
C7	0.0409 (14)	0.0577 (17)	0.0533 (15)	0.0020 (12)	−0.0038 (12)	0.0076 (13)
C8	0.0448 (13)	0.0532 (15)	0.0418 (13)	−0.0043 (12)	0.0058 (11)	0.0010 (12)
C9	0.0461 (14)	0.0488 (15)	0.0496 (15)	−0.0032 (12)	0.0024 (12)	0.0041 (13)
C10	0.0598 (16)	0.0647 (18)	0.0483 (16)	−0.0095 (14)	−0.0046 (13)	0.0020 (14)
C11	0.0699 (19)	0.0683 (19)	0.0484 (15)	−0.0157 (16)	0.0126 (14)	−0.0058 (14)
C12	0.0578 (17)	0.0641 (19)	0.0637 (18)	−0.0029 (14)	0.0166 (15)	−0.0065 (15)
C13	0.0487 (15)	0.0663 (18)	0.0545 (16)	0.0001 (13)	0.0073 (13)	−0.0024 (14)
C14	0.0351 (12)	0.0475 (15)	0.0505 (15)	0.0023 (11)	−0.0046 (11)	0.0014 (12)
C15	0.0570 (16)	0.0528 (17)	0.0700 (18)	−0.0022 (14)	0.0112 (14)	−0.0056 (14)
C16	0.0662 (18)	0.0510 (17)	0.095 (2)	−0.0083 (14)	0.0173 (17)	0.0024 (16)
C17	0.0549 (16)	0.070 (2)	0.0702 (19)	−0.0027 (15)	0.0131 (14)	0.0159 (16)
C18	0.0501 (15)	0.074 (2)	0.0530 (16)	−0.0008 (14)	0.0025 (13)	0.0036 (14)
C19	0.0456 (14)	0.0590 (17)	0.0523 (16)	−0.0047 (12)	−0.0013 (12)	−0.0008 (13)

Geometric parameters (Å, º) top

B1—O1	1.463 (3)	C8—C13	1.375 (3)
B1—O2	1.489 (3)	C8—C9	1.384 (3)
B1—C14	1.599 (4)	C9—C10	1.386 (3)
B1—N1	1.601 (3)	C10—C11	1.380 (4)
N1—C7	1.282 (3)	C10—H10	0.93
N1—C8	1.409 (3)	C11—C12	1.371 (4)
O1—C1	1.358 (3)	C11—H11	0.93
O2—C9	1.362 (3)	C12—C13	1.374 (3)
O3—C6	1.362 (3)	C12—H12	0.93
O3—H3'	0.84 (2)	C13—H13	0.93
C1—C6	1.387 (3)	C14—C19	1.387 (3)
C1—C2	1.399 (3)	C14—C15	1.388 (3)
C2—C3	1.399 (3)	C15—C16	1.379 (3)
C2—C7	1.426 (3)	C15—H15	0.93
C3—C4	1.357 (3)	C16—C17	1.370 (4)
C3—H3	0.93	C16—H16	0.93
C4—C5	1.396 (4)	C17—C18	1.367 (4)
C4—H4	0.93	C17—H17	0.93
C5—C6	1.370 (3)	C18—C19	1.375 (3)
C5—H5	0.93	C18—H18	0.93
C7—H7	0.93	C19—H19	0.93

O1—B1—O2	112.7 (2)	C9—C8—N1	106.6 (2)
O1—B1—C14	112.5 (2)	O2—C9—C8	114.0 (2)
O2—B1—C14	112.78 (19)	O2—C9—C10	126.4 (2)
O1—B1—N1	106.61 (18)	C8—C9—C10	119.6 (2)
O2—B1—N1	98.70 (18)	C11—C10—C9	117.5 (3)
C14—B1—N1	112.6 (2)	C11—C10—H10	121.2
C7—N1—C8	128.9 (2)	C9—C10—H10	121.2
C7—N1—B1	123.4 (2)	C12—C11—C10	122.3 (3)
C8—N1—B1	106.65 (18)	C12—C11—H11	118.9
C1—O1—B1	117.06 (18)	C10—C11—H11	118.9
C9—O2—B1	108.21 (18)	C11—C12—C13	120.6 (3)
C6—O3—H3'	112 (2)	C11—C12—H12	119.7
O1—C1—C6	117.6 (2)	C13—C12—H12	119.7
O1—C1—C2	123.2 (2)	C12—C13—C8	117.5 (3)
C6—C1—C2	119.2 (2)	C12—C13—H13	121.3
C1—C2—C3	119.7 (2)	C8—C13—H13	121.3
C1—C2—C7	117.9 (2)	C19—C14—C15	115.9 (2)
C3—C2—C7	122.0 (2)	C19—C14—B1	122.1 (2)
C4—C3—C2	120.6 (3)	C15—C14—B1	122.0 (2)
C4—C3—H3	119.7	C16—C15—C14	122.3 (3)
C2—C3—H3	119.7	C16—C15—H15	118.9
C3—C4—C5	119.4 (2)	C14—C15—H15	118.9
C3—C4—H4	120.3	C17—C16—C15	119.8 (3)
C5—C4—H4	120.3	C17—C16—H16	120.1
C6—C5—C4	121.0 (3)	C15—C16—H16	120.1
C6—C5—H5	119.5	C18—C17—C16	119.6 (3)
C4—C5—H5	119.5	C18—C17—H17	120.2
O3—C6—C5	119.2 (2)	C16—C17—H17	120.2
O3—C6—C1	120.7 (2)	C17—C18—C19	120.0 (3)
C5—C6—C1	120.1 (2)	C17—C18—H18	120.0
N1—C7—C2	119.0 (2)	C19—C18—H18	120.0
N1—C7—H7	120.5	C18—C19—C14	122.4 (2)
C2—C7—H7	120.5	C18—C19—H19	118.8
C13—C8—C9	122.5 (2)	C14—C19—H19	118.8
C13—C8—N1	130.8 (2)

O1—B1—N1—C7	29.0 (3)	C7—N1—C8—C13	26.0 (4)
O2—B1—N1—C7	145.9 (2)	B1—N1—C8—C13	−165.7 (3)
C14—B1—N1—C7	−94.8 (3)	C7—N1—C8—C9	−151.6 (2)
O1—B1—N1—C8	−140.00 (19)	B1—N1—C8—C9	16.7 (2)
O2—B1—N1—C8	−23.1 (2)	B1—O2—C9—C8	−13.6 (3)
C14—B1—N1—C8	96.1 (2)	B1—O2—C9—C10	167.3 (2)
O2—B1—O1—C1	−146.93 (18)	C13—C8—C9—O2	179.4 (2)
C14—B1—O1—C1	84.2 (2)	N1—C8—C9—O2	−2.7 (3)
N1—B1—O1—C1	−39.7 (3)	C13—C8—C9—C10	−1.5 (4)
O1—B1—O2—C9	133.55 (19)	N1—C8—C9—C10	176.3 (2)
C14—B1—O2—C9	−97.7 (2)	O2—C9—C10—C11	180.0 (2)
N1—B1—O2—C9	21.4 (2)	C8—C9—C10—C11	1.0 (4)
B1—O1—C1—C6	−154.4 (2)	C9—C10—C11—C12	0.4 (4)
B1—O1—C1—C2	28.1 (3)	C10—C11—C12—C13	−1.5 (4)
O1—C1—C2—C3	174.7 (2)	C11—C12—C13—C8	1.0 (4)
C6—C1—C2—C3	−2.7 (3)	C9—C8—C13—C12	0.5 (4)
O1—C1—C2—C7	2.3 (3)	N1—C8—C13—C12	−176.8 (2)
C6—C1—C2—C7	−175.1 (2)	O1—B1—C14—C19	−6.9 (3)
C1—C2—C3—C4	2.0 (4)	O2—B1—C14—C19	−135.7 (2)
C7—C2—C3—C4	174.1 (2)	N1—B1—C14—C19	113.6 (2)
C2—C3—C4—C5	−0.4 (4)	O1—B1—C14—C15	171.4 (2)
C3—C4—C5—C6	−0.4 (4)	O2—B1—C14—C15	42.6 (3)
C4—C5—C6—O3	−178.9 (2)	N1—B1—C14—C15	−68.0 (3)
C4—C5—C6—C1	−0.3 (4)	C19—C14—C15—C16	−1.0 (4)
O1—C1—C6—O3	2.8 (3)	B1—C14—C15—C16	−179.4 (2)
C2—C1—C6—O3	−179.6 (2)	C14—C15—C16—C17	0.3 (4)
O1—C1—C6—C5	−175.7 (2)	C15—C16—C17—C18	0.6 (4)
C2—C1—C6—C5	1.8 (3)	C16—C17—C18—C19	−0.9 (4)
C8—N1—C7—C2	164.0 (2)	C17—C18—C19—C14	0.1 (4)
B1—N1—C7—C2	−2.5 (3)	C15—C14—C19—C18	0.8 (3)
C1—C2—C7—N1	−14.9 (3)	B1—C14—C19—C18	179.2 (2)
C3—C2—C7—N1	172.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3′···O2ⁱ	0.84 (2)	1.97 (2)	2.740 (2)	152 (3)
C7—H7···O3ⁱⁱ	0.93	2.53	3.165 (3)	126

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄BNO₃
M_r	315.12
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	14.7245 (13), 11.196 (1), 18.4060 (16)
V (Å³)	3034.3 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.21 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	31865, 3317, 1942
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.127, 1.09
No. of reflections	3317
No. of parameters	220
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19

Computer programs: SMART (Bruker, 2000), SAINT-Plus NT (Bruker, 2001), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3'···O2ⁱ	0.84 (2)	1.97 (2)	2.740 (2)	152 (3)
C7—H7···O3ⁱⁱ	0.93	2.53	3.165 (3)	126

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1/2, y−1/2, z.

Acknowledgements

This work was supported by the Consejo Nacional de Ciencia y Tecnología (CIAM-59213).

References

Barba, V., Cuahutle, D., Santillan, R. & Farfán, N. (2001). Can. J. Chem. 79, 1229–1237. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2000). SMART. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SAINT-Plus NT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Höpfl, H. (1999). J. Organomet. Chem. 581, 129–149. Google Scholar
Höpfl, H., Sánchez, M., Farfán, N. & Barba, V. (1998). Can. J. Chem. 76, 1352–1360. Google Scholar
Lamère, J. F., Lacroix, P. G., Farfán, N., Rivera, J. M., Santillan, R. & Nakatani, K. (2006). J. Mater. Chem. 16, 2913–2920. Google Scholar
López-Ruiz, H., Mera-Moreno, I., Rojas-Lima, S., Santillan, R. & Farfán, N. (2008). Tetrahedron Lett. 49, 1674–1677. Google Scholar
Muñoz, B. M., Santillan, R., Rodríguez, M., Méndez, J. M., Romero, M., Farfán, N., Lacroix, P. G., Nakatani, K., Ramos-Ortíz, G. & Maldonado, J. L. (2008). J. Organomet. Chem. 693, 1321–1334. Google Scholar
Reyes, H., Rivera, J. M., Farfán, N., Santillan, R., Lacroix, P. G., Lepetit, C. & Nakatani, K. (2005). J. Organomet. Chem. 690, 3737–3745. Web of Science CSD CrossRef CAS Google Scholar
Rodríguez, M., Ochoa, M. E., Rodríguez, C., Santillan, R., Barba, V. & Farfán, N. (2005a). J. Organomet. Chem. 692, 2425–2435. Google Scholar
Rodríguez, M., Ochoa, M. E., Santillan, R., Farfán, N. & Barba, V. (2005b). J. Organomet. Chem. 692, 2975–2988. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar