(Dodecafluorosubphthalocyaninato)(4-methylphenolato)boron(III).

In the title compound, C(31)H(7)BF(12)N(6)O, mol-ecules are arranged into one-dimensional columns with an inter-molecular B⋯B distance of 5.3176 (8) Å. Bowl-shaped mol-ecules are arranged within the columns in a concave bowl-to-ligand arrangement separated by a ring centroid distance of 3.532 (2) Å between the benzene ring of the 4-methyl-phen-oxy ligand and one of the three five-membered rings of a symmetry-related mol-ecule.

Related literature

For a general review of boronsubphthalocyanine compounds (BsubPcs), see: Claessens et al. (2002 ▶). For the application of BsubPcs in organic light-emitting diodes, see: Morse et al. (2010a ▶) and references cited therein. For applications of BsubPcs in organic solar cells, see: Gommans et al. (2009 ▶). For the first reported synthesis, characterization and crystal structure of PhO-F12BsubPc, see: Claessens & Torres (2002 ▶). For a synthetic process to obtain the precursor compound, Br-F12BsubPc, see: Sharman & van Lier (2005 ▶); Morse et al. (2010b ▶).

Experimental

Crystal data

C31H7BF12N6O

M = 718.24

Monoclinic,

a = 14.6522 (5) Å

b = 10.5510 (6) Å

c = 18.0010 (7) Å

β = 96.663 (3)°

V = 2764.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 150 K

0.46 × 0.42 × 0.34 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.764, T max = 0.959

16887 measured reflections

6256 independent reflections

3481 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.172

S = 1.03

6256 reflections

460 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.30 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042716/jj2067sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042716/jj2067Isup2.hkl

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

C31H7BF12N6O	F(000) = 1424
Mr = 718.24	Dx = 1.726 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 16887 reflections
a = 14.6522 (5) Å	θ = 2.6–27.5°
b = 10.5510 (6) Å	µ = 0.16 mm−1
c = 18.0010 (7) Å	T = 150 K
β = 96.663 (3)°	Block, purple
V = 2764.1 (2) Å3	0.46 × 0.42 × 0.34 mm
Z = 4

Nonius KappaCCD diffractometer	6256 independent reflections
Radiation source: fine-focus sealed tube	3481 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.6°
φ scans and ω scans with κ offsets	h = −18→18
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −13→13
Tmin = 0.764, Tmax = 0.959	l = −23→23
16887 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0902P)2 + 0.2514P] where P = (Fo2 + 2Fc2)/3
6256 reflections	(Δ/σ)max = 0.001
460 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.30 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
F1	0.53576 (13)	0.27010 (17)	0.50181 (10)	0.0538 (5)
F2	0.62959 (14)	0.29013 (18)	0.63991 (10)	0.0619 (5)
F3	0.81470 (14)	0.29484 (19)	0.65863 (9)	0.0643 (6)
F4	0.91201 (12)	0.28163 (17)	0.54072 (9)	0.0516 (5)
F5	1.08623 (11)	0.37830 (19)	0.33494 (9)	0.0536 (5)
F6	1.17681 (11)	0.5008 (2)	0.23366 (10)	0.0627 (6)
F7	1.09226 (12)	0.56366 (19)	0.09845 (10)	0.0577 (5)
F8	0.91311 (11)	0.50438 (15)	0.05849 (8)	0.0425 (4)
F9	0.57526 (10)	0.56024 (14)	0.03931 (8)	0.0364 (4)
F10	0.40881 (11)	0.66504 (17)	0.05162 (9)	0.0476 (4)
F11	0.31482 (11)	0.60452 (19)	0.16583 (11)	0.0588 (5)
F12	0.38054 (11)	0.43226 (18)	0.27000 (9)	0.0506 (5)
O1	0.72879 (13)	0.09082 (16)	0.22748 (10)	0.0338 (5)
N1	0.72624 (15)	0.2315 (2)	0.33623 (12)	0.0306 (5)
N2	0.88549 (16)	0.2812 (2)	0.36128 (12)	0.0346 (6)
N3	0.80863 (14)	0.2979 (2)	0.23845 (11)	0.0287 (5)
N4	0.73305 (14)	0.4059 (2)	0.13397 (11)	0.0297 (5)
N5	0.64793 (14)	0.2999 (2)	0.22105 (11)	0.0294 (5)
N6	0.56821 (15)	0.2881 (2)	0.32889 (12)	0.0348 (6)
C1	0.64781 (19)	0.2520 (2)	0.36801 (15)	0.0319 (6)
C2	0.67586 (19)	0.2593 (3)	0.44816 (15)	0.0344 (7)
C3	0.6281 (2)	0.2706 (3)	0.50962 (16)	0.0407 (7)
C4	0.6750 (2)	0.2810 (3)	0.57947 (16)	0.0470 (8)
C5	0.7710 (3)	0.2829 (3)	0.58906 (15)	0.0469 (8)
C6	0.8201 (2)	0.2749 (3)	0.52897 (16)	0.0410 (7)
C7	0.7738 (2)	0.2598 (3)	0.45805 (15)	0.0353 (7)
C8	0.80436 (19)	0.2517 (3)	0.38416 (14)	0.0323 (6)
C9	0.88473 (18)	0.3097 (3)	0.28843 (14)	0.0319 (6)
C10	0.95087 (18)	0.3763 (3)	0.24878 (15)	0.0341 (6)
C11	1.04161 (19)	0.4099 (3)	0.26770 (16)	0.0399 (7)
C12	1.08789 (19)	0.4732 (3)	0.21697 (17)	0.0435 (7)
C13	1.0438 (2)	0.5054 (3)	0.14710 (16)	0.0414 (7)
C14	0.95285 (19)	0.4748 (3)	0.12730 (15)	0.0350 (6)
C15	0.90513 (17)	0.4115 (2)	0.17733 (14)	0.0299 (6)
C16	0.81024 (17)	0.3691 (2)	0.17553 (14)	0.0298 (6)
C17	0.65355 (17)	0.3781 (2)	0.16128 (14)	0.0303 (6)
C18	0.56452 (17)	0.4394 (2)	0.14843 (14)	0.0298 (6)
C19	0.52869 (18)	0.5275 (3)	0.09645 (14)	0.0317 (6)
C20	0.44506 (18)	0.5812 (3)	0.10268 (16)	0.0363 (7)
C21	0.39572 (18)	0.5493 (3)	0.16124 (17)	0.0405 (7)
C22	0.42956 (18)	0.4611 (3)	0.21442 (16)	0.0386 (7)
C23	0.51408 (18)	0.4049 (2)	0.20818 (15)	0.0323 (6)
C24	0.57225 (18)	0.3200 (3)	0.25680 (14)	0.0319 (6)
C25	0.74723 (19)	0.0818 (2)	0.15342 (15)	0.0330 (6)
C26	0.8368 (2)	0.0748 (3)	0.13729 (16)	0.0368 (7)
H26A	0.8855	0.0669	0.1767	0.044*
C27	0.8561 (2)	0.0793 (3)	0.06386 (16)	0.0404 (7)
H27A	0.9181	0.0752	0.0535	0.048*
C28	0.7860 (2)	0.0899 (3)	0.00501 (16)	0.0421 (7)
C29	0.6966 (2)	0.0895 (3)	0.02170 (16)	0.0396 (7)
H29A	0.6478	0.0917	−0.0180	0.048*
C30	0.6757 (2)	0.0858 (3)	0.09520 (16)	0.0366 (7)
H30A	0.6136	0.0860	0.1055	0.044*
C31	0.8089 (3)	0.1065 (3)	−0.07462 (17)	0.0565 (9)
H31A	0.7518	0.1119	−0.1088	0.085*
H31B	0.8450	0.0337	−0.0884	0.085*
H31C	0.8445	0.1844	−0.0780	0.085*
B1	0.7282 (2)	0.2205 (3)	0.25372 (17)	0.0310 (7)

	U11	U22	U33	U12	U13	U23
F1	0.0586 (12)	0.0578 (12)	0.0494 (11)	0.0048 (9)	0.0245 (9)	0.0038 (9)
F2	0.0932 (14)	0.0602 (13)	0.0372 (10)	0.0038 (11)	0.0279 (10)	0.0013 (9)
F3	0.0989 (15)	0.0645 (13)	0.0276 (9)	0.0151 (11)	−0.0004 (9)	−0.0035 (8)
F4	0.0577 (12)	0.0556 (12)	0.0390 (10)	0.0108 (9)	−0.0050 (8)	−0.0072 (8)
F5	0.0401 (10)	0.0752 (13)	0.0436 (10)	−0.0023 (9)	−0.0037 (8)	0.0029 (9)
F6	0.0362 (10)	0.0909 (16)	0.0612 (12)	−0.0162 (10)	0.0067 (9)	−0.0018 (11)
F7	0.0476 (10)	0.0745 (14)	0.0540 (11)	−0.0162 (9)	0.0186 (9)	0.0036 (10)
F8	0.0486 (10)	0.0449 (10)	0.0351 (9)	−0.0025 (8)	0.0099 (7)	0.0056 (8)
F9	0.0389 (9)	0.0381 (9)	0.0318 (8)	−0.0049 (7)	0.0019 (7)	0.0055 (7)
F10	0.0438 (9)	0.0486 (11)	0.0490 (10)	0.0067 (8)	0.0001 (8)	0.0148 (9)
F11	0.0384 (10)	0.0699 (13)	0.0693 (13)	0.0131 (9)	0.0124 (9)	0.0191 (10)
F12	0.0383 (9)	0.0670 (12)	0.0489 (10)	0.0020 (8)	0.0157 (8)	0.0106 (9)
O1	0.0487 (12)	0.0254 (10)	0.0288 (10)	−0.0013 (8)	0.0106 (9)	0.0009 (8)
N1	0.0390 (13)	0.0257 (12)	0.0278 (12)	0.0014 (10)	0.0063 (10)	0.0030 (9)
N2	0.0429 (14)	0.0325 (13)	0.0285 (12)	0.0076 (11)	0.0042 (10)	0.0002 (10)
N3	0.0342 (12)	0.0260 (12)	0.0259 (11)	0.0017 (10)	0.0034 (9)	−0.0004 (9)
N4	0.0328 (12)	0.0297 (12)	0.0268 (11)	−0.0015 (10)	0.0035 (10)	−0.0022 (10)
N5	0.0345 (12)	0.0274 (12)	0.0264 (11)	−0.0019 (10)	0.0048 (10)	0.0025 (10)
N6	0.0394 (13)	0.0303 (13)	0.0358 (13)	−0.0041 (11)	0.0093 (11)	0.0037 (10)
C1	0.0423 (16)	0.0252 (14)	0.0301 (14)	0.0004 (12)	0.0120 (13)	0.0027 (11)
C2	0.0470 (17)	0.0252 (14)	0.0327 (15)	0.0050 (12)	0.0123 (13)	0.0046 (12)
C3	0.0513 (19)	0.0336 (16)	0.0393 (17)	0.0032 (14)	0.0137 (15)	0.0049 (13)
C4	0.077 (2)	0.0359 (17)	0.0316 (16)	0.0048 (16)	0.0229 (16)	0.0015 (13)
C5	0.079 (2)	0.0369 (17)	0.0247 (15)	0.0089 (16)	0.0047 (15)	−0.0004 (13)
C6	0.055 (2)	0.0323 (16)	0.0348 (16)	0.0096 (14)	0.0015 (14)	0.0001 (13)
C7	0.0508 (18)	0.0271 (14)	0.0278 (15)	0.0045 (13)	0.0046 (13)	−0.0001 (12)
C8	0.0420 (17)	0.0262 (14)	0.0287 (15)	0.0048 (12)	0.0048 (13)	0.0022 (11)
C9	0.0361 (15)	0.0295 (15)	0.0300 (14)	0.0075 (12)	0.0031 (12)	−0.0003 (12)
C10	0.0351 (15)	0.0313 (15)	0.0364 (15)	0.0041 (12)	0.0058 (12)	−0.0057 (13)
C11	0.0390 (17)	0.0438 (18)	0.0368 (16)	0.0030 (14)	0.0039 (14)	−0.0047 (14)
C12	0.0295 (15)	0.0519 (19)	0.0499 (18)	−0.0036 (14)	0.0087 (14)	−0.0064 (16)
C13	0.0413 (17)	0.0409 (18)	0.0449 (17)	−0.0050 (14)	0.0177 (14)	−0.0026 (14)
C14	0.0415 (16)	0.0318 (15)	0.0334 (15)	0.0030 (13)	0.0119 (13)	−0.0027 (13)
C15	0.0326 (14)	0.0270 (14)	0.0308 (14)	0.0035 (11)	0.0070 (12)	0.0020 (11)
C16	0.0361 (15)	0.0259 (14)	0.0283 (13)	0.0015 (12)	0.0068 (12)	0.0000 (12)
C17	0.0343 (15)	0.0289 (15)	0.0279 (14)	0.0005 (12)	0.0048 (11)	0.0002 (12)
C18	0.0321 (14)	0.0274 (14)	0.0289 (14)	−0.0048 (12)	−0.0003 (12)	−0.0009 (11)
C19	0.0322 (15)	0.0343 (15)	0.0286 (14)	−0.0090 (12)	0.0044 (12)	0.0007 (12)
C20	0.0315 (15)	0.0361 (16)	0.0399 (16)	−0.0036 (12)	−0.0024 (13)	0.0054 (13)
C21	0.0266 (15)	0.0473 (18)	0.0480 (18)	0.0026 (13)	0.0060 (13)	0.0060 (15)
C22	0.0314 (15)	0.0451 (17)	0.0409 (16)	−0.0057 (13)	0.0107 (13)	0.0018 (14)
C23	0.0322 (14)	0.0318 (15)	0.0321 (15)	−0.0040 (12)	0.0002 (12)	−0.0006 (12)
C24	0.0326 (14)	0.0311 (15)	0.0323 (14)	−0.0055 (12)	0.0055 (12)	0.0000 (12)
C25	0.0468 (17)	0.0227 (14)	0.0309 (15)	0.0022 (12)	0.0100 (13)	0.0010 (11)
C26	0.0440 (17)	0.0296 (15)	0.0369 (16)	0.0037 (13)	0.0046 (13)	−0.0011 (12)
C27	0.0435 (17)	0.0340 (16)	0.0460 (18)	0.0012 (13)	0.0150 (15)	−0.0014 (14)
C28	0.060 (2)	0.0288 (16)	0.0379 (17)	−0.0007 (14)	0.0098 (15)	−0.0015 (13)
C29	0.0547 (19)	0.0323 (16)	0.0309 (15)	0.0002 (14)	0.0007 (14)	0.0005 (12)
C30	0.0402 (16)	0.0286 (15)	0.0412 (17)	−0.0039 (12)	0.0054 (13)	−0.0037 (12)
C31	0.085 (3)	0.049 (2)	0.0384 (18)	−0.0006 (18)	0.0210 (17)	0.0022 (15)
B1	0.0375 (18)	0.0295 (17)	0.0263 (15)	0.0006 (14)	0.0045 (14)	0.0015 (13)

F1—C3	1.343 (3)	C5—C6	1.370 (4)
F2—C4	1.343 (3)	C6—C7	1.383 (4)
F3—C5	1.345 (3)	C7—C8	1.454 (4)
F4—C6	1.341 (3)	C9—C10	1.450 (4)
F5—C11	1.349 (3)	C10—C11	1.380 (4)
F6—C12	1.335 (3)	C10—C15	1.429 (4)
F7—C13	1.339 (3)	C11—C12	1.373 (4)
F8—C14	1.343 (3)	C12—C13	1.388 (4)
F9—C19	1.344 (3)	C13—C14	1.377 (4)
F10—C20	1.340 (3)	C14—C15	1.375 (4)
F11—C21	1.332 (3)	C15—C16	1.457 (4)
F12—C22	1.333 (3)	C17—C18	1.450 (4)
O1—C25	1.394 (3)	C18—C19	1.379 (4)
O1—B1	1.448 (4)	C18—C23	1.421 (4)
N1—C1	1.359 (3)	C19—C20	1.367 (4)
N1—C8	1.368 (3)	C20—C21	1.387 (4)
N1—B1	1.493 (4)	C21—C22	1.385 (4)
N2—C8	1.339 (4)	C22—C23	1.389 (4)
N2—C9	1.344 (3)	C23—C24	1.457 (4)
N3—C9	1.355 (3)	C25—C26	1.379 (4)
N3—C16	1.361 (3)	C25—C30	1.394 (4)
N3—B1	1.485 (4)	C26—C27	1.384 (4)
N4—C16	1.339 (3)	C26—H26A	0.9500
N4—C17	1.348 (3)	C27—C28	1.392 (4)
N5—C24	1.362 (3)	C27—H27A	0.9500
N5—C17	1.366 (3)	C28—C29	1.378 (4)
N5—B1	1.507 (4)	C28—C31	1.519 (4)
N6—C1	1.345 (3)	C29—C30	1.393 (4)
N6—C24	1.349 (3)	C29—H29A	0.9500
C1—C2	1.456 (4)	C30—H30A	0.9500
C2—C3	1.381 (4)	C31—H31A	0.9800
C2—C7	1.426 (4)	C31—H31B	0.9800
C3—C4	1.366 (4)	C31—H31C	0.9800
C4—C5	1.397 (5)
C25—O1—B1	112.7 (2)	N4—C16—N3	122.0 (2)
C1—N1—C8	113.3 (2)	N4—C16—C15	131.7 (2)
C1—N1—B1	123.1 (2)	N3—C16—C15	105.0 (2)
C8—N1—B1	121.9 (2)	N4—C17—N5	123.5 (2)
C8—N2—C9	116.4 (2)	N4—C17—C18	130.1 (2)
C9—N3—C16	114.2 (2)	N5—C17—C18	105.0 (2)
C9—N3—B1	122.5 (2)	C19—C18—C23	119.7 (2)
C16—N3—B1	123.2 (2)	C19—C18—C17	132.3 (2)
C16—N4—C17	116.3 (2)	C23—C18—C17	107.6 (2)
C24—N5—C17	113.9 (2)	F9—C19—C20	119.7 (2)
C24—N5—B1	122.9 (2)	F9—C19—C18	120.4 (2)
C17—N5—B1	121.8 (2)	C20—C19—C18	119.9 (2)
C1—N6—C24	116.2 (2)	F10—C20—C19	120.4 (3)
N6—C1—N1	123.3 (2)	F10—C20—C21	118.8 (2)
N6—C1—C2	129.2 (2)	C19—C20—C21	120.9 (3)
N1—C1—C2	105.7 (2)	F11—C21—C22	120.1 (3)
C3—C2—C7	119.8 (3)	F11—C21—C20	119.2 (3)
C3—C2—C1	133.4 (3)	C22—C21—C20	120.8 (3)
C7—C2—C1	106.8 (2)	F12—C22—C21	119.4 (3)
F1—C3—C4	119.3 (3)	F12—C22—C23	121.8 (3)
F1—C3—C2	120.9 (3)	C21—C22—C23	118.8 (3)
C4—C3—C2	119.8 (3)	C22—C23—C18	119.9 (2)
F2—C4—C3	120.5 (3)	C22—C23—C24	132.7 (3)
F2—C4—C5	119.0 (3)	C18—C23—C24	107.0 (2)
C3—C4—C5	120.5 (3)	N6—C24—N5	123.0 (2)
F3—C5—C6	120.3 (3)	N6—C24—C23	130.1 (2)
F3—C5—C4	118.7 (3)	N5—C24—C23	105.3 (2)
C6—C5—C4	121.0 (3)	C26—C25—O1	120.0 (2)
F4—C6—C5	118.8 (3)	C26—C25—C30	119.6 (3)
F4—C6—C7	121.8 (3)	O1—C25—C30	120.3 (2)
C5—C6—C7	119.4 (3)	C25—C26—C27	120.2 (3)
C6—C7—C2	119.6 (3)	C25—C26—H26A	119.9
C6—C7—C8	133.0 (3)	C27—C26—H26A	119.9
C2—C7—C8	107.3 (2)	C26—C27—C28	121.0 (3)
N2—C8—N1	123.4 (2)	C26—C27—H27A	119.5
N2—C8—C7	130.2 (3)	C28—C27—H27A	119.5
N1—C8—C7	105.2 (2)	C29—C28—C27	118.0 (3)
N2—C9—N3	122.7 (2)	C29—C28—C31	121.7 (3)
N2—C9—C10	131.2 (2)	C27—C28—C31	120.2 (3)
N3—C9—C10	105.3 (2)	C28—C29—C30	121.8 (3)
C11—C10—C15	119.6 (3)	C28—C29—H29A	119.1
C11—C10—C9	133.0 (3)	C30—C29—H29A	119.1
C15—C10—C9	107.4 (2)	C29—C30—C25	119.1 (3)
F5—C11—C12	119.5 (3)	C29—C30—H30A	120.4
F5—C11—C10	120.7 (3)	C25—C30—H30A	120.4
C12—C11—C10	119.8 (3)	C28—C31—H31A	109.5
F6—C12—C11	120.1 (3)	C28—C31—H31B	109.5
F6—C12—C13	119.4 (3)	H31A—C31—H31B	109.5
C11—C12—C13	120.5 (3)	C28—C31—H31C	109.5
F7—C13—C14	120.6 (3)	H31A—C31—H31C	109.5
F7—C13—C12	118.6 (3)	H31B—C31—H31C	109.5
C14—C13—C12	120.8 (3)	O1—B1—N3	115.1 (2)
F8—C14—C15	121.2 (2)	O1—B1—N1	113.5 (2)
F8—C14—C13	119.1 (2)	N3—B1—N1	104.4 (2)
C15—C14—C13	119.6 (3)	O1—B1—N5	115.6 (2)
C14—C15—C10	119.6 (2)	N3—B1—N5	102.8 (2)
C14—C15—C16	133.7 (2)	N1—B1—N5	103.9 (2)
C10—C15—C16	106.7 (2)