[5-Hydroxy-3-phenyl-1-(pyridin-2-yl)pyrazol-5-olato]diphenylboron.

In the title compound, C(26)H(20)BN(3)O, the B atom has tetra-hedral geometry and is linked to two phenyl rings, the O atom of the hy-droxy-pyrazole ring and the N atom of the pyridinyl ring. A six-membered BOCNCN ring forms by coordination of the B atom and the pyridinyl N atom. The BOCNCN ring has an envelope conformation [dihedral angle = 36.7 (1)° between the planar ring atoms and the flap] with the B atom out of the plane. In the 1-(2-pyridin-yl)-3-phenyl-5-hy-droxy-pyrazole group, the pyridinyl ring, the phenyl ring and the pyrazole ring are almost coplanar: the pyrazole ring makes a dihedral angle of 9.56 (8)° with the pyridinyl ring and 17.68 (7)° with the phenyl ring. The crystal structure is stabilized by π-π stacking inter-actions involving the pyridinyl and pyrazole rings of centrosymmetrically related mol-ecules, with ring centroid separations of 3.54 (5) Å.

Related literature

For general synthesis of diaryl­borinates, see: Hagan et al. (2000 ▶). For their synthesis and biological applications, see: Scorei & Popa (2010 ▶); Baker, Akama et al. (2006 ▶); Baker, Zhang et al. (2006 ▶). For luminescent organoboron compounds, see: Cui et al. (2005 ▶).

Experimental

Crystal data

C26H20BN3O

M = 401.26

Triclinic,

a = 9.7309 (1) Å

b = 9.8830 (1) Å

c = 11.2162 (1) Å

α = 78.966 (1)°

β = 81.795 (1)°

γ = 79.993 (1)°

V = 1035.91 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.44 × 0.31 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

19866 measured reflections

5044 independent reflections

3923 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.03

5044 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 global, I. DOI: 10.1107/S1600536811010634/pk2309sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010634/pk2309Isup2.hkl

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

C26H20BN3O	Z = 2
Mr = 401.26	F(000) = 420
Triclinic, P1	Dx = 1.286 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7309 (1) Å	Cell parameters from 8036 reflections
b = 9.8830 (1) Å	θ = 2.6–27.8°
c = 11.2162 (1) Å	µ = 0.08 mm−1
α = 78.966 (1)°	T = 296 K
β = 81.795 (1)°	Block, pale-yellow
γ = 79.993 (1)°	0.44 × 0.31 × 0.23 mm
V = 1035.91 (2) Å3

Bruker APEXII CCD diffractometer	3923 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 28.2°, θmin = 1.9°
φ and ω scans	h = −12→12
19866 measured reflections	k = −13→13
5044 independent reflections	l = −14→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.1687P] where P = (Fo2 + 2Fc2)/3
5044 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 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
N1	0.34223 (10)	0.62671 (9)	0.41391 (8)	0.0395 (2)
N2	0.33209 (10)	0.73403 (10)	0.47857 (9)	0.0425 (2)
C3	0.20130 (12)	0.74313 (12)	0.53352 (10)	0.0409 (2)
C4	0.12724 (12)	0.64242 (12)	0.50700 (10)	0.0430 (3)
H4A	0.0351	0.6293	0.5354	0.052*
C5	0.22001 (11)	0.56935 (11)	0.43117 (9)	0.0386 (2)
C6	0.46530 (11)	0.58301 (11)	0.34599 (9)	0.0367 (2)
N7	0.45672 (9)	0.49060 (9)	0.27425 (8)	0.0384 (2)
C8	0.57501 (13)	0.44224 (13)	0.20644 (11)	0.0468 (3)
H8A	0.5706	0.3766	0.1583	0.056*
C9	0.70060 (13)	0.48605 (13)	0.20602 (12)	0.0510 (3)
H9A	0.7800	0.4516	0.1578	0.061*
C10	0.70778 (13)	0.58275 (13)	0.27872 (12)	0.0495 (3)
H10A	0.7922	0.6145	0.2790	0.059*
C11	0.59005 (12)	0.63144 (12)	0.35022 (11)	0.0443 (3)
H11A	0.5936	0.6953	0.4003	0.053*
C12	0.15138 (13)	0.85394 (12)	0.60693 (10)	0.0443 (3)
C13	0.24704 (15)	0.92376 (14)	0.64202 (13)	0.0583 (3)
H13A	0.3428	0.8949	0.6246	0.070*
C14	0.20174 (19)	1.03558 (16)	0.70253 (14)	0.0709 (4)
H14A	0.2668	1.0816	0.7255	0.085*
C15	0.05972 (19)	1.07890 (16)	0.72888 (14)	0.0706 (4)
H15A	0.0288	1.1555	0.7678	0.085*
C16	−0.03519 (17)	1.00873 (17)	0.69750 (13)	0.0681 (4)
H16A	−0.1308	1.0368	0.7168	0.082*
C17	0.00942 (14)	0.89644 (15)	0.63743 (12)	0.0568 (3)
H17A	−0.0563	0.8490	0.6173	0.068*
O18	0.21775 (8)	0.45786 (8)	0.38208 (7)	0.0434 (2)
B19	0.30310 (14)	0.45262 (13)	0.25937 (12)	0.0403 (3)
C20	0.23337 (12)	0.57188 (12)	0.15691 (10)	0.0415 (2)
C21	0.29568 (15)	0.68316 (13)	0.08918 (11)	0.0519 (3)
H21A	0.3863	0.6910	0.1015	0.062*
C22	0.22721 (18)	0.78278 (15)	0.00390 (13)	0.0644 (4)
H22A	0.2717	0.8562	−0.0395	0.077*
C23	0.09335 (17)	0.77314 (15)	−0.01651 (13)	0.0641 (4)
H23A	0.0470	0.8398	−0.0736	0.077*
C24	0.02870 (15)	0.66393 (16)	0.04825 (13)	0.0595 (3)
H24A	−0.0614	0.6563	0.0345	0.071*
C25	0.09721 (13)	0.56573 (14)	0.13358 (12)	0.0512 (3)
H25A	0.0515	0.4931	0.1770	0.061*
C26	0.32831 (12)	0.29614 (12)	0.23273 (11)	0.0443 (3)
C27	0.33295 (15)	0.26571 (15)	0.11599 (13)	0.0581 (3)
H27A	0.3125	0.3381	0.0517	0.070*
C28	0.36740 (19)	0.12997 (17)	0.09288 (17)	0.0760 (5)
H28A	0.3698	0.1124	0.0140	0.091*
C29	0.39796 (18)	0.02182 (16)	0.18673 (19)	0.0793 (5)
H29A	0.4220	−0.0690	0.1713	0.095*
C30	0.39304 (18)	0.04790 (15)	0.30304 (17)	0.0729 (4)
H30A	0.4132	−0.0253	0.3668	0.087*
C31	0.35801 (15)	0.18321 (13)	0.32561 (14)	0.0574 (3)
H31A	0.3542	0.1993	0.4051	0.069*

	U11	U22	U33	U12	U13	U23
N1	0.0393 (5)	0.0417 (5)	0.0400 (5)	−0.0107 (4)	0.0002 (4)	−0.0123 (4)
N2	0.0449 (5)	0.0423 (5)	0.0429 (5)	−0.0092 (4)	−0.0006 (4)	−0.0145 (4)
C3	0.0414 (6)	0.0433 (6)	0.0367 (5)	−0.0053 (5)	−0.0029 (4)	−0.0059 (5)
C4	0.0390 (6)	0.0503 (6)	0.0400 (6)	−0.0101 (5)	−0.0007 (4)	−0.0082 (5)
C5	0.0409 (6)	0.0411 (6)	0.0348 (5)	−0.0114 (4)	−0.0039 (4)	−0.0046 (4)
C6	0.0394 (6)	0.0363 (5)	0.0334 (5)	−0.0067 (4)	−0.0031 (4)	−0.0037 (4)
N7	0.0410 (5)	0.0390 (5)	0.0358 (5)	−0.0082 (4)	−0.0018 (4)	−0.0078 (4)
C8	0.0480 (7)	0.0477 (6)	0.0452 (6)	−0.0070 (5)	0.0017 (5)	−0.0148 (5)
C9	0.0429 (6)	0.0553 (7)	0.0527 (7)	−0.0059 (5)	0.0055 (5)	−0.0132 (6)
C10	0.0397 (6)	0.0542 (7)	0.0548 (7)	−0.0129 (5)	−0.0015 (5)	−0.0075 (6)
C11	0.0433 (6)	0.0468 (6)	0.0452 (6)	−0.0119 (5)	−0.0033 (5)	−0.0102 (5)
C12	0.0490 (6)	0.0443 (6)	0.0377 (6)	−0.0037 (5)	−0.0008 (5)	−0.0083 (5)
C13	0.0558 (8)	0.0589 (8)	0.0641 (8)	−0.0105 (6)	0.0038 (6)	−0.0259 (7)
C14	0.0851 (11)	0.0630 (9)	0.0709 (10)	−0.0198 (8)	0.0069 (8)	−0.0306 (8)
C15	0.0924 (12)	0.0559 (8)	0.0577 (8)	0.0035 (8)	0.0082 (8)	−0.0211 (7)
C16	0.0624 (9)	0.0760 (10)	0.0573 (8)	0.0126 (8)	0.0042 (7)	−0.0194 (7)
C17	0.0503 (7)	0.0692 (9)	0.0492 (7)	−0.0017 (6)	−0.0006 (6)	−0.0165 (6)
O18	0.0475 (5)	0.0454 (4)	0.0407 (4)	−0.0170 (3)	0.0010 (3)	−0.0111 (3)
B19	0.0418 (7)	0.0426 (7)	0.0391 (6)	−0.0122 (5)	−0.0031 (5)	−0.0094 (5)
C20	0.0468 (6)	0.0417 (6)	0.0384 (6)	−0.0071 (5)	−0.0029 (5)	−0.0137 (5)
C21	0.0604 (8)	0.0500 (7)	0.0481 (7)	−0.0154 (6)	−0.0102 (6)	−0.0058 (5)
C22	0.0899 (11)	0.0516 (8)	0.0517 (8)	−0.0157 (7)	−0.0138 (7)	0.0003 (6)
C23	0.0821 (10)	0.0590 (8)	0.0488 (7)	0.0073 (7)	−0.0205 (7)	−0.0096 (6)
C24	0.0532 (8)	0.0710 (9)	0.0558 (8)	0.0020 (7)	−0.0143 (6)	−0.0191 (7)
C25	0.0484 (7)	0.0551 (7)	0.0515 (7)	−0.0087 (6)	−0.0056 (5)	−0.0118 (6)
C26	0.0432 (6)	0.0429 (6)	0.0500 (6)	−0.0119 (5)	−0.0035 (5)	−0.0120 (5)
C27	0.0684 (9)	0.0546 (8)	0.0551 (8)	−0.0127 (6)	−0.0027 (6)	−0.0192 (6)
C28	0.0874 (11)	0.0704 (10)	0.0808 (11)	−0.0198 (8)	0.0051 (9)	−0.0426 (9)
C29	0.0809 (11)	0.0464 (8)	0.1152 (15)	−0.0155 (7)	0.0041 (10)	−0.0313 (9)
C30	0.0781 (11)	0.0430 (7)	0.0974 (12)	−0.0147 (7)	−0.0125 (9)	−0.0047 (8)
C31	0.0664 (9)	0.0458 (7)	0.0626 (8)	−0.0147 (6)	−0.0107 (6)	−0.0073 (6)

N1—C6	1.3736 (14)	C16—C17	1.382 (2)
N1—N2	1.3778 (12)	C16—H16A	0.9300
N1—C5	1.3784 (14)	C17—H17A	0.9300
N2—C3	1.3286 (14)	O18—B19	1.5077 (15)
C3—C4	1.4221 (16)	B19—C26	1.6016 (17)
C3—C12	1.4695 (16)	B19—C20	1.6113 (17)
C4—C5	1.3599 (16)	C20—C21	1.3910 (17)
C4—H4A	0.9300	C20—C25	1.4003 (17)
C5—O18	1.3273 (13)	C21—C22	1.3862 (19)
C6—N7	1.3474 (13)	C21—H21A	0.9300
C6—C11	1.3900 (15)	C22—C23	1.377 (2)
N7—C8	1.3528 (14)	C22—H22A	0.9300
N7—B19	1.6412 (15)	C23—C24	1.376 (2)
C8—C9	1.3647 (17)	C23—H23A	0.9300
C8—H8A	0.9300	C24—C25	1.3799 (19)
C9—C10	1.3860 (17)	C24—H24A	0.9300
C9—H9A	0.9300	C25—H25A	0.9300
C10—C11	1.3715 (16)	C26—C27	1.3915 (17)
C10—H10A	0.9300	C26—C31	1.3940 (18)
C11—H11A	0.9300	C27—C28	1.3897 (19)
C12—C17	1.3857 (18)	C27—H27A	0.9300
C12—C13	1.3890 (18)	C28—C29	1.374 (3)
C13—C14	1.3815 (19)	C28—H28A	0.9300
C13—H13A	0.9300	C29—C30	1.370 (2)
C14—C15	1.381 (2)	C29—H29A	0.9300
C14—H14A	0.9300	C30—C31	1.3838 (19)
C15—C16	1.366 (2)	C30—H30A	0.9300
C15—H15A	0.9300	C31—H31A	0.9300
C6—N1—N2	121.20 (9)	C16—C17—C12	120.47 (14)
C6—N1—C5	126.52 (9)	C16—C17—H17A	119.8
N2—N1—C5	112.22 (9)	C12—C17—H17A	119.8
C3—N2—N1	103.56 (9)	C5—O18—B19	115.85 (8)
N2—C3—C4	112.44 (10)	O18—B19—C26	109.26 (9)
N2—C3—C12	118.30 (10)	O18—B19—C20	110.01 (9)
C4—C3—C12	129.22 (11)	C26—B19—C20	116.51 (9)
C5—C4—C3	105.22 (10)	O18—B19—N7	105.44 (8)
C5—C4—H4A	127.4	C26—B19—N7	107.22 (9)
C3—C4—H4A	127.4	C20—B19—N7	107.79 (9)
O18—C5—C4	134.33 (10)	C21—C20—C25	116.08 (11)
O18—C5—N1	118.96 (9)	C21—C20—B19	125.87 (11)
C4—C5—N1	106.55 (9)	C25—C20—B19	118.05 (10)
N7—C6—N1	115.43 (9)	C22—C21—C20	122.18 (13)
N7—C6—C11	122.21 (10)	C22—C21—H21A	118.9
N1—C6—C11	122.36 (10)	C20—C21—H21A	118.9
C6—N7—C8	118.15 (10)	C23—C22—C21	120.03 (14)
C6—N7—B19	119.99 (9)	C23—C22—H22A	120.0
C8—N7—B19	121.51 (9)	C21—C22—H22A	120.0
N7—C8—C9	122.52 (11)	C24—C23—C22	119.41 (13)
N7—C8—H8A	118.7	C24—C23—H23A	120.3
C9—C8—H8A	118.7	C22—C23—H23A	120.3
C8—C9—C10	118.84 (11)	C23—C24—C25	120.19 (13)
C8—C9—H9A	120.6	C23—C24—H24A	119.9
C10—C9—H9A	120.6	C25—C24—H24A	119.9
C11—C10—C9	119.84 (11)	C24—C25—C20	122.10 (13)
C11—C10—H10A	120.1	C24—C25—H25A	118.9
C9—C10—H10A	120.1	C20—C25—H25A	118.9
C10—C11—C6	118.42 (11)	C27—C26—C31	116.55 (12)
C10—C11—H11A	120.8	C27—C26—B19	122.56 (11)
C6—C11—H11A	120.8	C31—C26—B19	120.71 (11)
C17—C12—C13	118.37 (12)	C28—C27—C26	121.72 (14)
C17—C12—C3	121.57 (11)	C28—C27—H27A	119.1
C13—C12—C3	119.98 (11)	C26—C27—H27A	119.1
C14—C13—C12	120.83 (14)	C29—C28—C27	119.89 (15)
C14—C13—H13A	119.6	C29—C28—H28A	120.1
C12—C13—H13A	119.6	C27—C28—H28A	120.1
C15—C14—C13	119.88 (15)	C30—C29—C28	119.93 (14)
C15—C14—H14A	120.1	C30—C29—H29A	120.0
C13—C14—H14A	120.1	C28—C29—H29A	120.0
C16—C15—C14	119.73 (14)	C29—C30—C31	119.93 (15)
C16—C15—H15A	120.1	C29—C30—H30A	120.0
C14—C15—H15A	120.1	C31—C30—H30A	120.0
C15—C16—C17	120.67 (14)	C30—C31—C26	121.98 (14)
C15—C16—H16A	119.7	C30—C31—H31A	119.0
C17—C16—H16A	119.7	C26—C31—H31A	119.0
C6—N1—N2—C3	−178.54 (9)	C4—C5—O18—B19	149.85 (13)
C5—N1—N2—C3	−1.17 (12)	N1—C5—O18—B19	−35.58 (14)
N1—N2—C3—C4	0.83 (12)	C5—O18—B19—C26	162.66 (9)
N1—N2—C3—C12	−176.99 (9)	C5—O18—B19—C20	−68.27 (12)
N2—C3—C4—C5	−0.21 (13)	C5—O18—B19—N7	47.71 (12)
C12—C3—C4—C5	177.31 (11)	C6—N7—B19—O18	−34.70 (13)
C3—C4—C5—O18	174.52 (12)	C8—N7—B19—O18	152.14 (10)
C3—C4—C5—N1	−0.52 (12)	C6—N7—B19—C26	−151.05 (9)
C6—N1—C5—O18	2.33 (16)	C8—N7—B19—C26	35.80 (13)
N2—N1—C5—O18	−174.86 (9)	C6—N7—B19—C20	82.77 (11)
C6—N1—C5—C4	178.28 (10)	C8—N7—B19—C20	−90.38 (12)
N2—N1—C5—C4	1.08 (12)	O18—B19—C20—C21	117.35 (12)
N2—N1—C6—N7	−171.46 (9)	C26—B19—C20—C21	−117.62 (13)
C5—N1—C6—N7	11.57 (16)	N7—B19—C20—C21	2.88 (15)
N2—N1—C6—C11	8.11 (16)	O18—B19—C20—C25	−61.86 (13)
C5—N1—C6—C11	−168.85 (11)	C26—B19—C20—C25	63.16 (14)
N1—C6—N7—C8	−179.10 (9)	N7—B19—C20—C25	−176.34 (9)
C11—C6—N7—C8	1.32 (16)	C25—C20—C21—C22	0.30 (18)
N1—C6—N7—B19	7.52 (14)	B19—C20—C21—C22	−178.92 (12)
C11—C6—N7—B19	−172.06 (10)	C20—C21—C22—C23	−0.3 (2)
C6—N7—C8—C9	−1.63 (17)	C21—C22—C23—C24	−0.1 (2)
B19—N7—C8—C9	171.64 (11)	C22—C23—C24—C25	0.5 (2)
N7—C8—C9—C10	0.66 (19)	C23—C24—C25—C20	−0.6 (2)
C8—C9—C10—C11	0.64 (19)	C21—C20—C25—C24	0.15 (18)
C9—C10—C11—C6	−0.92 (18)	B19—C20—C25—C24	179.44 (11)
N7—C6—C11—C10	−0.07 (17)	O18—B19—C26—C27	145.00 (12)
N1—C6—C11—C10	−179.62 (10)	C20—B19—C26—C27	19.60 (17)
N2—C3—C12—C17	161.16 (11)	N7—B19—C26—C27	−101.21 (13)
C4—C3—C12—C17	−16.24 (19)	O18—B19—C26—C31	−40.18 (15)
N2—C3—C12—C13	−15.47 (17)	C20—B19—C26—C31	−165.58 (11)
C4—C3—C12—C13	167.14 (12)	N7—B19—C26—C31	73.61 (13)
C17—C12—C13—C14	−2.0 (2)	C31—C26—C27—C28	−0.9 (2)
C3—C12—C13—C14	174.76 (13)	B19—C26—C27—C28	174.12 (13)
C12—C13—C14—C15	0.1 (2)	C26—C27—C28—C29	0.0 (2)
C13—C14—C15—C16	1.6 (2)	C27—C28—C29—C30	0.6 (3)
C14—C15—C16—C17	−1.3 (2)	C28—C29—C30—C31	−0.3 (3)
C15—C16—C17—C12	−0.6 (2)	C29—C30—C31—C26	−0.6 (2)
C13—C12—C17—C16	2.2 (2)	C27—C26—C31—C30	1.2 (2)
C3—C12—C17—C16	−174.44 (12)	B19—C26—C31—C30	−173.89 (13)