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

Lee, K.-I.; Bin, H.-R.; Lee, D.-M.; Kim, C.-H.

doi:10.1107/S1600536811010634

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o979

doi:10.1107/S1600536811010634

Open

access

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

Kee-In Lee,^a Hye-Rin Bin,^a Do-Min Lee ^a and Chong-Hyeak Kim ^b ^*

^aGreen Chemistry Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea, and ^bCenter for Chemical Analysis, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea
^*Correspondence e-mail: chkim@krict.re.kr

(Received 26 February 2011; accepted 22 March 2011; online 26 March 2011)

In the title compound, C₂₆H₂₀BN₃O, the B atom has tetrahedral geometry and is linked to two phenyl rings, the O atom of the hydroxypyrazole 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-pyridinyl)-3-phenyl-5-hydroxypyrazole 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 interactions involving the pyridinyl and pyrazole rings of centrosymmetrically related molecules, 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_r = 401.26
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.106
S = 1.03
5044 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010634/pk2309sup1.cif

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

checkCIF report

Comment top

Recently, boron-containing compounds have become increasingly frequent in preventive and chemotherapeutic agents for high-malignancy cancer (Scorei & Popa, 2010), their antibacterial and antifungal agents effect on cell growth (Baker, Akama et al., 2006; Baker, Zhang et al., 2006), and also in luminescent compounds for potential applications in organic light emitting devices (Cui et al., 2005). Diarylborinates have been prepared by the reaction of diarylborinic acids with dimethylaminoethanol-type ligands (Hagan et al., 2000). Interestingly, we identify an unusual diphenylborinate from 1-(2-pyridinyl)pyrazole trifluoromethanesulfonate with phenylboronic acid in Suzuki-Miyaura coupling conditions. Here we report the crystal structure of the title compound (Figs. 1 and 2). In the title compound, C₂₆H₂₀BN₃O, B atom has a tetrahedral geometry linked with the two C atoms of the two phenyl rings, the O atom of the hydroxypyrazole ring and the N atom of the pyridinyl ring. The six membered ring of –B(19)—O(18)—C(5)—N(1)—C(6)—N(7)- motif forms by the coordination between B atom and N atom of the pyridinyl ring. The –B—O—C—N—C—N– ring has an envelope conformation with B out of plane. The B atom deviate from the the mean plane and forms a dihedral angle of 36.7 (1) ° with B(19)—O(18) 1.508 (2) Å and B(19)—N(7) 1.641 (2) Å. In the 1-(2-pyridinyl)-3-phenyl-5-hydroxypyrazole 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 interactions involving the pyridinyl and pyrazole rings of centrosymmetrically related molecules, with a ring centroid separations of 3.54 (5) Å.

Related literature top

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 top

The title compound was synthesized from the reaction of 1-(2-pyridinyl)pyrazole trifluoromethanesulfonate (185 mg, 0.5 mmol) and phenylboronic acid (183 mg, 1.5 mmol) with K₃PO₄ (318 mg, 1.5 mmol) in the presence of PdCl₂{1,1'-bis(diphenylphosphino)ferrocene} (33 mg, 0.04 mmol) and 1,1'-bis(diphenylphosphino)ferrocene (11 mg, 0.02 mmol) in anhydrous 1,4-dioxane (5 ml) for 20 hr at 100 °C. The reaction mixture was rinsed with toluene (5 ml) and the resulting solution was filtered by aid of a Celite pad. The organic layer was dried over Na₂SO₄ and the solvents were removed. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate = 7/1) to give the title compound (30 mg, 8% yield). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids. H atoms are shown as small spheres of arbitary radius.
	Fig. 2. The molecular packing structure of the title compound along the a axis. [Symmetry codes: (i) x, y, z; (ii) -x, -y, -z.]

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

Crystal data top

C₂₆H₂₀BN₃O	Z = 2
M_r = 401.26	F(000) = 420
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0466P)² + 0.1687P] where P = (F_o² + 2F_c²)/3
5044 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₆H₂₀BN₃O	γ = 79.993 (1)°
M_r = 401.26	V = 1035.91 (2) Å³
Triclinic, P1	Z = 2
a = 9.7309 (1) Å	Mo Kα radiation
b = 9.8830 (1) Å	µ = 0.08 mm⁻¹
c = 11.2162 (1) Å	T = 296 K
α = 78.966 (1)°	0.44 × 0.31 × 0.23 mm
β = 81.795 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3923 reflections with I > 2σ(I)
19866 measured reflections	R_int = 0.019
5044 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
5044 reflections	Δρ_min = −0.19 e Å⁻³
280 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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀BN₃O
M_r	401.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.7309 (1), 9.8830 (1), 11.2162 (1)
α, β, γ (°)	78.966 (1), 81.795 (1), 79.993 (1)
V (Å³)	1035.91 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.44 × 0.31 × 0.23

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19866, 5044, 3923
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.106, 1.03
No. of reflections	5044
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

References

Baker, S. J., Akama, T., Zhang, Y.-K., Sauro, V., Pandit, C., Singh, R., Kully, M., Khan, J., Plattner, J. J., Benkovic, S. J., Lee, V. & Maples, K. R. (2006). Bioorg. Med. Chem. Lett. 16, 5963–5967. Web of Science CrossRef PubMed CAS Google Scholar
Baker, S. J., Zhang, Y.-K., Akama, T., Lau, A., Zhou, H., Hernandez, V., Mao, W., Alley, M. R. K., Sanders, V. & Plattner, J. J. (2006). J. Med. Chem. 49, 4447–4450. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cui, Y., Liu, Q.-D., Bai, D.-R., Jia, W.-L., Tao, Y. & Wang, S. (2005). Inorg. Chem. 44, 601–609. Web of Science CSD CrossRef PubMed CAS Google Scholar
Hagan, H., Reinoso, S., Albrecht, M., Boersma, J., Spek, A. L. & van Koten, G. (2000). J. Organomet. Chem. 608, 27–33. Google Scholar
Scorei, R. I. & Popa, R. Jr (2010). Anticancer Agents Med. Chem. 10, 346–351. Web of Science PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar