(4-Acetyl-phenolato)(subphthalo-cyaninato)boron(III).

In the title compound, C(32)H(19)BN(6)O(2), the B atom adopts a BON(3) tetra-hedral coordination geometry. In the crystal, pairs of mol-ecules are associated through aromatic π-π stacking inter-actions between the concave faces of the boronsubphthalocyanine fragments at a centroid-centroid distance of 3.4951 (19) Å and a weaker inter-action of the same type between the convex faces of the same group [centroid-centroid separation = 3.5669 (18) Å] also occurs.

Related literature

For related structures and discussion of electronic effects, see: Paton et al. (2010 ▶). For further synthetic details, see: Claessens et al. (2002) ▶; Zyskowski & Kennedy (2000 ▶).

Experimental

Crystal data

C32H19BN6O2

M = 530.34

Triclinic,

a = 10.5471 (8) Å

b = 10.5786 (5) Å

c = 11.5375 (9) Å

α = 77.446 (4)°

β = 88.817 (3)°

γ = 83.966 (4)°

V = 1249.54 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.08 × 0.08 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.858, T max = 1.002

8602 measured reflections

4273 independent reflections

2393 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.146

S = 0.98

4273 reflections

372 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046003/hb5719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046003/hb5719Isup2.hkl

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

C32H19BN6O2	Z = 2
Mr = 530.34	F(000) = 548
Triclinic, P1	Dx = 1.410 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5471 (8) Å	Cell parameters from 8602 reflections
b = 10.5786 (5) Å	θ = 2.6–25.0°
c = 11.5375 (9) Å	µ = 0.09 mm−1
α = 77.446 (4)°	T = 150 K
β = 88.817 (3)°	Block, magenta
γ = 83.966 (4)°	0.08 × 0.08 × 0.05 mm
V = 1249.54 (15) Å3

Nonius KappaCCD diffractometer	4273 independent reflections
Radiation source: fine-focus sealed tube	2393 reflections with I > 2σ(I)
graphite	Rint = 0.078
Detector resolution: 9 pixels mm-1	θmax = 25.0°, θmin = 2.6°
φ scans and ω scans with κ offsets	h = −12→12
Absorption correction: multi-scan from symmetry-related measurements (SORTAV; Blessing, 1995)	k = −11→12
Tmin = 0.858, Tmax = 1.002	l = −12→13
8602 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.0559P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
4273 reflections	Δρmax = 0.23 e Å−3
372 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXTL (Version 6.1; Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0102 (19)

Experimental. (SORTAV; Blessing, 1995)

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
O1	0.84545 (19)	0.21044 (17)	0.32764 (17)	0.0390 (6)
O2	1.2585 (2)	0.5988 (2)	0.3568 (2)	0.0493 (6)
N1	0.7983 (2)	0.1720 (2)	0.1263 (2)	0.0334 (6)
N2	0.7054 (2)	−0.0271 (2)	0.1944 (2)	0.0373 (6)
N3	0.6430 (2)	0.1576 (2)	0.2758 (2)	0.0342 (6)
N4	0.5094 (2)	0.3473 (2)	0.2935 (2)	0.0360 (6)
N5	0.6990 (2)	0.3625 (2)	0.1770 (2)	0.0338 (6)
N6	0.8102 (2)	0.3770 (2)	−0.0067 (2)	0.0356 (6)
C1	0.8329 (3)	0.2456 (3)	0.0194 (3)	0.0348 (8)
C2	0.8656 (3)	0.1542 (3)	−0.0569 (3)	0.0351 (8)
C3	0.9125 (3)	0.1700 (3)	−0.1722 (3)	0.0416 (8)
H3A	0.9329	0.2524	−0.2155	0.050*
C4	0.9285 (3)	0.0610 (3)	−0.2218 (3)	0.0448 (9)
H4A	0.9639	0.0685	−0.2990	0.054*
C5	0.8939 (3)	−0.0592 (3)	−0.1609 (3)	0.0429 (8)
H5A	0.9039	−0.1313	−0.1983	0.052*
C6	0.8452 (3)	−0.0755 (3)	−0.0474 (3)	0.0385 (8)
H6A	0.8211	−0.1574	−0.0064	0.046*
C7	0.8325 (3)	0.0317 (3)	0.0055 (3)	0.0343 (8)
C8	0.7819 (3)	0.0472 (3)	0.1197 (3)	0.0348 (8)
C9	0.6314 (3)	0.0325 (3)	0.2668 (3)	0.0335 (7)
C10	0.5121 (3)	0.0000 (3)	0.3263 (2)	0.0332 (8)
C11	0.4524 (3)	−0.1143 (3)	0.3485 (3)	0.0366 (8)
H11A	0.4909	−0.1905	0.3256	0.044*
C12	0.3356 (3)	−0.1134 (3)	0.4047 (3)	0.0396 (8)
H12A	0.2946	−0.1911	0.4235	0.048*
C13	0.2768 (3)	−0.0006 (3)	0.4345 (3)	0.0389 (8)
H13A	0.1966	−0.0030	0.4735	0.047*
C14	0.3323 (3)	0.1145 (3)	0.4087 (3)	0.0368 (8)
H14A	0.2901	0.1917	0.4268	0.044*
C15	0.4514 (3)	0.1145 (3)	0.3557 (2)	0.0320 (7)
C16	0.5348 (3)	0.2169 (3)	0.3156 (3)	0.0331 (7)
C17	0.5876 (3)	0.4175 (3)	0.2165 (3)	0.0340 (8)
C18	0.5647 (3)	0.5469 (3)	0.1419 (3)	0.0341 (8)
C19	0.4719 (3)	0.6503 (3)	0.1443 (3)	0.0396 (8)
H19A	0.4082	0.6439	0.2041	0.048*
C20	0.4753 (3)	0.7628 (3)	0.0569 (3)	0.0406 (8)
H20A	0.4158	0.8361	0.0594	0.049*
C21	0.5650 (3)	0.7704 (3)	−0.0351 (3)	0.0404 (8)
H21A	0.5648	0.8488	−0.0938	0.048*
C22	0.6538 (3)	0.6665 (3)	−0.0425 (3)	0.0367 (8)
H22A	0.7112	0.6703	−0.1074	0.044*
C23	0.6558 (3)	0.5557 (3)	0.0492 (3)	0.0329 (7)
C24	0.7357 (3)	0.4319 (3)	0.0686 (3)	0.0338 (7)
C25	0.9382 (3)	0.2846 (3)	0.3453 (3)	0.0343 (8)
C26	0.9781 (3)	0.2682 (3)	0.4620 (3)	0.0372 (8)
H26A	0.9395	0.2093	0.5232	0.045*
C27	1.0731 (3)	0.3366 (3)	0.4899 (3)	0.0398 (8)
H27A	1.1005	0.3232	0.5700	0.048*
C28	1.1292 (3)	0.4251 (3)	0.4021 (3)	0.0338 (7)
C29	1.0886 (3)	0.4412 (3)	0.2854 (3)	0.0361 (8)
H29A	1.1262	0.5014	0.2245	0.043*
C30	0.9946 (3)	0.3714 (3)	0.2561 (3)	0.0366 (8)
H30A	0.9689	0.3828	0.1758	0.044*
C31	1.2310 (3)	0.5024 (3)	0.4297 (3)	0.0406 (8)
C32	1.2969 (4)	0.4619 (3)	0.5468 (3)	0.0601 (10)
H32A	1.3636	0.5190	0.5500	0.090*
H32B	1.3355	0.3718	0.5572	0.090*
H32C	1.2351	0.4684	0.6104	0.090*
B1	0.7555 (3)	0.2280 (3)	0.2299 (3)	0.0362 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0413 (13)	0.0386 (12)	0.0360 (13)	−0.0134 (10)	−0.0056 (10)	−0.0005 (10)
O2	0.0517 (15)	0.0442 (13)	0.0549 (16)	−0.0146 (11)	0.0061 (12)	−0.0127 (12)
N1	0.0343 (15)	0.0325 (14)	0.0330 (16)	−0.0058 (11)	0.0030 (12)	−0.0054 (12)
N2	0.0372 (16)	0.0352 (14)	0.0393 (16)	−0.0060 (12)	0.0015 (13)	−0.0068 (12)
N3	0.0364 (16)	0.0334 (14)	0.0334 (15)	−0.0067 (12)	0.0020 (12)	−0.0071 (12)
N4	0.0418 (16)	0.0333 (15)	0.0335 (16)	−0.0085 (12)	0.0027 (13)	−0.0067 (12)
N5	0.0368 (16)	0.0335 (14)	0.0318 (16)	−0.0063 (12)	0.0009 (12)	−0.0074 (12)
N6	0.0357 (16)	0.0345 (14)	0.0376 (16)	−0.0065 (12)	0.0006 (13)	−0.0083 (12)
C1	0.0325 (18)	0.0363 (18)	0.0355 (19)	−0.0065 (14)	0.0010 (15)	−0.0062 (15)
C2	0.0315 (18)	0.0375 (18)	0.035 (2)	−0.0002 (14)	−0.0030 (15)	−0.0053 (15)
C3	0.040 (2)	0.0448 (19)	0.036 (2)	−0.0013 (15)	0.0007 (16)	−0.0017 (16)
C4	0.045 (2)	0.052 (2)	0.035 (2)	0.0063 (17)	−0.0049 (16)	−0.0100 (17)
C5	0.041 (2)	0.045 (2)	0.044 (2)	0.0033 (15)	−0.0056 (17)	−0.0135 (17)
C6	0.0305 (19)	0.0419 (19)	0.042 (2)	−0.0021 (14)	−0.0051 (16)	−0.0079 (16)
C7	0.0276 (18)	0.0376 (18)	0.038 (2)	−0.0025 (14)	−0.0015 (15)	−0.0087 (15)
C8	0.0322 (19)	0.0325 (17)	0.038 (2)	−0.0014 (14)	0.0022 (15)	−0.0047 (15)
C9	0.0347 (19)	0.0286 (16)	0.0363 (19)	−0.0027 (14)	−0.0040 (15)	−0.0049 (14)
C10	0.0366 (19)	0.0342 (17)	0.0281 (18)	−0.0083 (14)	−0.0014 (14)	−0.0025 (14)
C11	0.041 (2)	0.0368 (18)	0.0319 (19)	−0.0070 (15)	−0.0025 (16)	−0.0067 (14)
C12	0.046 (2)	0.0345 (18)	0.039 (2)	−0.0126 (15)	−0.0011 (16)	−0.0058 (15)
C13	0.0367 (19)	0.0419 (19)	0.0368 (19)	−0.0120 (15)	0.0001 (15)	−0.0018 (15)
C14	0.041 (2)	0.0347 (17)	0.0348 (19)	−0.0082 (14)	0.0050 (16)	−0.0060 (14)
C15	0.0349 (19)	0.0332 (17)	0.0281 (18)	−0.0083 (14)	−0.0031 (14)	−0.0045 (14)
C16	0.038 (2)	0.0363 (18)	0.0263 (17)	−0.0087 (15)	−0.0010 (15)	−0.0074 (14)
C17	0.039 (2)	0.0368 (18)	0.0291 (18)	−0.0076 (15)	0.0006 (15)	−0.0113 (15)
C18	0.040 (2)	0.0302 (17)	0.0332 (19)	−0.0080 (14)	0.0021 (15)	−0.0083 (14)
C19	0.041 (2)	0.0389 (19)	0.042 (2)	−0.0123 (15)	0.0013 (16)	−0.0111 (16)
C20	0.037 (2)	0.0354 (18)	0.051 (2)	−0.0053 (14)	−0.0063 (17)	−0.0103 (16)
C21	0.044 (2)	0.0346 (18)	0.041 (2)	−0.0085 (16)	−0.0061 (17)	−0.0025 (15)
C22	0.0381 (19)	0.0377 (18)	0.0358 (19)	−0.0131 (15)	−0.0027 (15)	−0.0064 (15)
C23	0.0374 (19)	0.0281 (16)	0.0355 (19)	−0.0109 (14)	0.0002 (15)	−0.0083 (14)
C24	0.0335 (19)	0.0382 (18)	0.0300 (19)	−0.0081 (14)	0.0013 (15)	−0.0058 (15)
C25	0.0315 (18)	0.0347 (17)	0.037 (2)	−0.0046 (14)	0.0003 (15)	−0.0091 (15)
C26	0.040 (2)	0.0438 (18)	0.0281 (19)	−0.0090 (15)	0.0039 (15)	−0.0059 (14)
C27	0.037 (2)	0.0471 (19)	0.034 (2)	−0.0037 (15)	−0.0004 (16)	−0.0081 (16)
C28	0.0323 (18)	0.0350 (17)	0.036 (2)	−0.0040 (14)	−0.0002 (15)	−0.0113 (15)
C29	0.040 (2)	0.0316 (17)	0.036 (2)	−0.0057 (14)	0.0064 (15)	−0.0053 (14)
C30	0.044 (2)	0.0359 (17)	0.0294 (18)	−0.0081 (15)	−0.0008 (15)	−0.0042 (15)
C31	0.040 (2)	0.0415 (19)	0.043 (2)	−0.0057 (15)	0.0073 (17)	−0.0145 (16)
C32	0.063 (3)	0.066 (2)	0.058 (3)	−0.0208 (19)	−0.015 (2)	−0.019 (2)
B1	0.033 (2)	0.037 (2)	0.037 (2)	−0.0075 (17)	0.0000 (18)	−0.0036 (17)

O1—C25	1.361 (3)	C12—C13	1.394 (4)
O2—C31	1.229 (3)	C12—H12A	0.9500
N1—C8	1.367 (3)	C13—C14	1.377 (4)
N1—C1	1.373 (3)	C13—H13A	0.9500
B1—O1	1.457 (4)	C14—C15	1.386 (4)
B1—N1	1.487 (4)	C14—H14A	0.9500
B1—N3	1.494 (4)	C15—C16	1.458 (4)
B1—N5	1.487 (4)	C17—C18	1.449 (4)
N2—C9	1.342 (4)	C18—C19	1.393 (4)
N2—C8	1.351 (3)	C18—C23	1.418 (4)
N3—C16	1.364 (4)	C19—C20	1.385 (4)
N3—C9	1.368 (3)	C19—H19A	0.9500
N4—C16	1.346 (3)	C20—C21	1.402 (4)
N4—C17	1.354 (3)	C20—H20A	0.9500
N5—C17	1.371 (4)	C21—C22	1.383 (4)
N5—C24	1.376 (3)	C21—H21A	0.9500
N6—C24	1.343 (4)	C22—C23	1.396 (4)
N6—C1	1.353 (3)	C22—H22A	0.9500
C1—C2	1.454 (4)	C23—C24	1.457 (4)
C2—C3	1.392 (4)	C25—C26	1.388 (4)
C2—C7	1.413 (4)	C25—C30	1.391 (4)
C3—C4	1.388 (4)	C26—C27	1.378 (4)
C3—H3A	0.9500	C26—H26A	0.9500
C4—C5	1.393 (4)	C27—C28	1.390 (4)
C4—H4A	0.9500	C27—H27A	0.9500
C5—C6	1.379 (4)	C28—C29	1.390 (4)
C5—H5A	0.9500	C28—C31	1.495 (4)
C6—C7	1.393 (4)	C29—C30	1.386 (4)
C6—H6A	0.9500	C29—H29A	0.9500
C7—C8	1.447 (4)	C30—H30A	0.9500
C9—C10	1.458 (4)	C31—C32	1.490 (5)
C10—C11	1.395 (4)	C32—H32A	0.9800
C10—C15	1.412 (4)	C32—H32B	0.9800
C11—C12	1.381 (4)	C32—H32C	0.9800
C11—H11A	0.9500
C25—O1—B1	130.3 (2)	N4—C16—C15	130.5 (3)
C8—N1—C1	112.4 (2)	N3—C16—C15	105.9 (2)
C8—N1—B1	122.7 (2)	N4—C17—N5	122.4 (2)
C1—N1—B1	123.5 (2)	N4—C17—C18	130.3 (3)
C9—N2—C8	116.7 (2)	N5—C17—C18	106.1 (2)
C16—N3—C9	113.1 (2)	C19—C18—C23	120.4 (3)
C16—N3—B1	123.2 (2)	C19—C18—C17	132.4 (3)
C9—N3—B1	123.1 (3)	C23—C18—C17	107.1 (3)
C16—N4—C17	116.8 (3)	C20—C19—C18	118.1 (3)
C17—N5—C24	112.3 (2)	C20—C19—H19A	121.0
C17—N5—B1	123.0 (2)	C18—C19—H19A	121.0
C24—N5—B1	123.1 (3)	C19—C20—C21	121.2 (3)
C24—N6—C1	117.2 (2)	C19—C20—H20A	119.4
N6—C1—N1	121.8 (3)	C21—C20—H20A	119.4
N6—C1—C2	130.9 (3)	C22—C21—C20	121.6 (3)
N1—C1—C2	105.8 (2)	C22—C21—H21A	119.2
C3—C2—C7	120.6 (3)	C20—C21—H21A	119.2
C3—C2—C1	132.4 (3)	C21—C22—C23	117.4 (3)
C7—C2—C1	106.9 (3)	C21—C22—H22A	121.3
C4—C3—C2	117.7 (3)	C23—C22—H22A	121.3
C4—C3—H3A	121.2	C22—C23—C18	121.1 (3)
C2—C3—H3A	121.2	C22—C23—C24	131.3 (3)
C3—C4—C5	121.6 (3)	C18—C23—C24	107.4 (2)
C3—C4—H4A	119.2	N6—C24—N5	122.5 (3)
C5—C4—H4A	119.2	N6—C24—C23	130.7 (3)
C6—C5—C4	121.2 (3)	N5—C24—C23	105.4 (3)
C6—C5—H5A	119.4	O1—C25—C26	115.6 (3)
C4—C5—H5A	119.4	O1—C25—C30	124.9 (3)
C5—C6—C7	118.0 (3)	C26—C25—C30	119.4 (3)
C5—C6—H6A	121.0	C27—C26—C25	120.6 (3)
C7—C6—H6A	121.0	C27—C26—H26A	119.7
C6—C7—C2	120.8 (3)	C25—C26—H26A	119.7
C6—C7—C8	131.3 (3)	C26—C27—C28	120.6 (3)
C2—C7—C8	107.8 (3)	C26—C27—H27A	119.7
N2—C8—N1	122.8 (3)	C28—C27—H27A	119.7
N2—C8—C7	129.5 (3)	C27—C28—C29	118.5 (3)
N1—C8—C7	105.8 (2)	C27—C28—C31	122.0 (3)
N2—C9—N3	122.2 (3)	C29—C28—C31	119.5 (3)
N2—C9—C10	131.0 (3)	C30—C29—C28	121.4 (3)
N3—C9—C10	105.3 (3)	C30—C29—H29A	119.3
C11—C10—C15	120.6 (3)	C28—C29—H29A	119.3
C11—C10—C9	131.6 (3)	C29—C30—C25	119.5 (3)
C15—C10—C9	107.6 (2)	C29—C30—H30A	120.3
C12—C11—C10	117.9 (3)	C25—C30—H30A	120.3
C12—C11—H11A	121.1	O2—C31—C32	120.7 (3)
C10—C11—H11A	121.1	O2—C31—C28	120.2 (3)
C11—C12—C13	121.2 (3)	C32—C31—C28	119.1 (3)
C11—C12—H12A	119.4	C31—C32—H32A	109.5
C13—C12—H12A	119.4	C31—C32—H32B	109.5
C14—C13—C12	121.5 (3)	H32A—C32—H32B	109.5
C14—C13—H13A	119.2	C31—C32—H32C	109.5
C12—C13—H13A	119.2	H32A—C32—H32C	109.5
C13—C14—C15	118.1 (3)	H32B—C32—H32C	109.5
C13—C14—H14A	120.9	O1—B1—N5	118.0 (3)
C15—C14—H14A	120.9	O1—B1—N1	117.1 (3)
C14—C15—C10	120.6 (2)	N5—B1—N1	104.7 (3)
C14—C15—C16	132.4 (3)	O1—B1—N3	107.7 (2)
C10—C15—C16	107.0 (3)	N5—B1—N3	104.0 (3)
N4—C16—N3	122.2 (2)	N1—B1—N3	103.8 (2)

Table 1

Selected bond lengths (Å)

B1—O1	1.457 (4)
B1—N1	1.487 (4)
B1—N3	1.494 (4)
B1—N5	1.487 (4)