(4-Cyano-phenolato)(subphthalocyaninato)boron.

The crystal structure of the title compound, C(31)H(16)BN(7)O, (CNPhO-BsubPc) is characterized by pairs of π-π stacking inter-actions between the concave faces of inversion-related BsubPc fragments with a centroid-centroid distance of 3.600 (1) Å. In addition, these pairs of mol-ecules are linked into chains along [101] through further weak π-π stacking inter-actions with a centroid-centroid distance of 3.8587 (9) Å. There are also weak C-H⋯π(arene) inter-actions within the chains.

Related literature

For a general review of boronsubphthalocyanine compounds (BsubPcs), see: Claessens et al. (2002 ▶). For the synthesis of boronsubphthalocyanine and its derivatives, see: Zyskowski & Kennedy (2000 ▶); Claessens et al. (2003 ▶); Paton et al. (2011b ▶). For the application of BsubPcs in organic electronic devices, see: Morse et al. (2010 ▶) and references cited therein; Gommans et al. (2009) ▶. For related crystal structures of non-halogenated boronsubphthalocyanine derivatives, see: Potz et al. (2000 ▶); Paton et al. (2010 ▶, 2011a ▶,b ▶). For the treatment of disordered solvent mol­ecules, see: Athimoolam et al. (2005 ▶); Cox et al. (2003 ▶); Mohamed et al. (2003 ▶); Stähler et al. (2001 ▶).

Experimental

Crystal data

C31H16BN7O

M = 513.32

Monoclinic,

a = 16.2310 (3) Å

b = 27.5129 (7) Å

c = 13.4385 (2) Å

β = 119.4050 (12)°

V = 5228.00 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.40 × 0.30 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.711, T max = 0.994

21404 measured reflections

5914 independent reflections

4290 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.141

S = 1.06

5914 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.26 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 global, I. DOI: 10.1107/S1600536811000869/zl2323sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000869/zl2323Isup2.hkl

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

C31H16BN7O	F(000) = 2112
Mr = 513.32	Dx = 1.304 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 21404 reflections
a = 16.2310 (3) Å	θ = 2.6–27.5°
b = 27.5129 (7) Å	µ = 0.08 mm−1
c = 13.4385 (2) Å	T = 150 K
β = 119.4050 (12)°	Plate, purple
V = 5228.00 (18) Å3	0.40 × 0.30 × 0.12 mm
Z = 8

Nonius KappaCCD diffractometer	5914 independent reflections
Radiation source: fine-focus sealed tube	4290 reflections with I > 2σ(I)
graphite	Rint = 0.087
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.7°
φ scans and ω scans with κ offsets	h = −21→18
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −35→35
Tmin = 0.711, Tmax = 0.994	l = −17→17
21404 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0863P)2] where P = (Fo2 + 2Fc2)/3
5914 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.26 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
O1	0.45381 (6)	0.13599 (4)	0.37150 (8)	0.0282 (3)
N1	0.29842 (7)	0.16745 (5)	0.25275 (9)	0.0239 (3)
N2	0.20587 (8)	0.09502 (5)	0.20043 (10)	0.0279 (3)
N3	0.31564 (8)	0.11128 (5)	0.39600 (10)	0.0250 (3)
N4	0.34779 (8)	0.14317 (5)	0.57623 (10)	0.0269 (3)
N5	0.37213 (7)	0.19169 (5)	0.44565 (9)	0.0234 (3)
N6	0.32295 (8)	0.25170 (5)	0.30000 (10)	0.0256 (3)
N7	0.89695 (9)	0.09629 (6)	0.79845 (12)	0.0423 (4)
C1	0.28553 (9)	0.21531 (6)	0.22298 (12)	0.0244 (3)
C2	0.20815 (9)	0.21704 (6)	0.10579 (11)	0.0246 (3)
C3	0.16247 (10)	0.25605 (6)	0.03201 (12)	0.0276 (3)
H3A	0.1862	0.2883	0.0515	0.033*
C4	0.08163 (11)	0.24607 (6)	−0.07024 (12)	0.0319 (4)
H4A	0.0503	0.2718	−0.1225	0.038*
C5	0.04511 (10)	0.19906 (6)	−0.09831 (12)	0.0324 (4)
H5A	−0.0114	0.1937	−0.1685	0.039*
C6	0.08894 (10)	0.16012 (6)	−0.02685 (12)	0.0285 (3)
H6A	0.0637	0.1282	−0.0467	0.034*
C7	0.17179 (9)	0.16932 (6)	0.07568 (11)	0.0249 (3)
C8	0.22770 (9)	0.13839 (6)	0.17416 (11)	0.0245 (3)
C9	0.24642 (10)	0.08345 (6)	0.31192 (12)	0.0266 (3)
C10	0.21193 (10)	0.05125 (6)	0.36928 (12)	0.0295 (3)
C11	0.14170 (11)	0.01560 (6)	0.32724 (14)	0.0343 (4)
H11A	0.1111	0.0063	0.2491	0.041*
C12	0.11801 (12)	−0.00584 (6)	0.40292 (15)	0.0401 (4)
H12A	0.0717	−0.0308	0.3765	0.048*
C13	0.16061 (13)	0.00841 (7)	0.51697 (15)	0.0411 (4)
H13A	0.1427	−0.0070	0.5667	0.049*
C14	0.22856 (12)	0.04466 (6)	0.55934 (14)	0.0371 (4)
H14A	0.2566	0.0546	0.6369	0.044*
C15	0.25479 (10)	0.06624 (6)	0.48518 (12)	0.0294 (4)
C16	0.31566 (10)	0.10753 (6)	0.49800 (12)	0.0272 (3)
C17	0.36934 (9)	0.18587 (6)	0.54540 (11)	0.0250 (3)
C18	0.37682 (9)	0.23457 (6)	0.59076 (11)	0.0256 (3)
C19	0.38193 (9)	0.25146 (6)	0.69168 (12)	0.0290 (4)
H19A	0.3810	0.2296	0.7459	0.035*
C20	0.38842 (10)	0.30100 (6)	0.70979 (13)	0.0320 (4)
H20A	0.3938	0.3133	0.7788	0.038*
C21	0.38732 (10)	0.33359 (6)	0.62963 (13)	0.0333 (4)
H21A	0.3933	0.3674	0.6459	0.040*
C22	0.37760 (9)	0.31749 (6)	0.52658 (13)	0.0309 (4)
H22A	0.3741	0.3398	0.4707	0.037*
C23	0.37317 (9)	0.26767 (6)	0.50768 (11)	0.0257 (3)
C24	0.36076 (9)	0.23903 (6)	0.41071 (12)	0.0244 (3)
C25	0.54079 (9)	0.12725 (6)	0.46227 (12)	0.0252 (3)
C26	0.61048 (10)	0.11309 (6)	0.43571 (12)	0.0280 (3)
H26A	0.5952	0.1096	0.3582	0.034*
C27	0.70191 (10)	0.10419 (6)	0.52242 (12)	0.0286 (3)
H27A	0.7487	0.0937	0.5042	0.034*
C28	0.72545 (10)	0.11047 (6)	0.63614 (12)	0.0275 (3)
C29	0.65582 (11)	0.12432 (6)	0.66259 (13)	0.0316 (4)
H29A	0.6715	0.1285	0.7401	0.038*
C30	0.56400 (10)	0.13197 (6)	0.57646 (12)	0.0306 (4)
H30A	0.5165	0.1405	0.5951	0.037*
C31	0.82104 (11)	0.10284 (6)	0.72633 (13)	0.0308 (4)
B1	0.36726 (11)	0.15027 (7)	0.37081 (13)	0.0256 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0217 (5)	0.0396 (7)	0.0226 (5)	0.0049 (4)	0.0102 (4)	0.0000 (4)
N1	0.0231 (6)	0.0279 (8)	0.0215 (6)	0.0008 (5)	0.0115 (5)	−0.0012 (5)
N2	0.0302 (6)	0.0288 (8)	0.0261 (6)	0.0013 (5)	0.0150 (5)	−0.0032 (5)
N3	0.0261 (6)	0.0270 (7)	0.0226 (6)	0.0028 (5)	0.0124 (5)	−0.0001 (5)
N4	0.0241 (6)	0.0323 (8)	0.0236 (6)	0.0010 (5)	0.0111 (5)	−0.0002 (5)
N5	0.0199 (5)	0.0293 (8)	0.0206 (6)	0.0001 (5)	0.0096 (5)	−0.0011 (5)
N6	0.0215 (6)	0.0315 (8)	0.0245 (6)	−0.0016 (5)	0.0118 (5)	−0.0011 (5)
N7	0.0293 (7)	0.0455 (10)	0.0408 (8)	0.0011 (6)	0.0085 (7)	−0.0024 (7)
C1	0.0202 (7)	0.0311 (9)	0.0247 (7)	0.0004 (6)	0.0132 (6)	0.0009 (6)
C2	0.0210 (7)	0.0342 (9)	0.0207 (7)	0.0003 (6)	0.0118 (6)	−0.0003 (6)
C3	0.0263 (7)	0.0321 (9)	0.0267 (7)	0.0005 (6)	0.0148 (6)	0.0001 (6)
C4	0.0284 (8)	0.0426 (11)	0.0246 (7)	0.0067 (7)	0.0130 (6)	0.0051 (7)
C5	0.0241 (7)	0.0480 (11)	0.0218 (7)	0.0025 (7)	0.0086 (6)	−0.0022 (7)
C6	0.0259 (7)	0.0362 (10)	0.0240 (7)	0.0006 (6)	0.0126 (6)	−0.0041 (6)
C7	0.0238 (7)	0.0320 (9)	0.0223 (7)	0.0020 (6)	0.0139 (6)	−0.0027 (6)
C8	0.0235 (7)	0.0296 (9)	0.0225 (7)	0.0006 (6)	0.0130 (6)	−0.0045 (6)
C9	0.0290 (7)	0.0254 (9)	0.0270 (7)	0.0025 (6)	0.0151 (6)	−0.0027 (6)
C10	0.0334 (8)	0.0272 (9)	0.0311 (8)	0.0034 (6)	0.0183 (7)	−0.0004 (6)
C11	0.0360 (8)	0.0312 (10)	0.0364 (9)	0.0013 (7)	0.0183 (7)	−0.0005 (7)
C12	0.0448 (10)	0.0310 (10)	0.0494 (10)	−0.0049 (7)	0.0270 (8)	0.0001 (8)
C13	0.0520 (10)	0.0345 (11)	0.0458 (10)	−0.0010 (8)	0.0310 (9)	0.0073 (8)
C14	0.0452 (9)	0.0367 (11)	0.0341 (8)	−0.0003 (8)	0.0231 (8)	0.0027 (7)
C15	0.0309 (8)	0.0292 (9)	0.0297 (8)	0.0038 (6)	0.0160 (7)	0.0020 (6)
C16	0.0264 (7)	0.0329 (9)	0.0229 (7)	0.0037 (6)	0.0127 (6)	0.0013 (6)
C17	0.0183 (6)	0.0356 (10)	0.0204 (7)	0.0022 (6)	0.0089 (6)	−0.0005 (6)
C18	0.0168 (6)	0.0345 (9)	0.0246 (7)	0.0004 (6)	0.0096 (6)	−0.0032 (6)
C19	0.0198 (7)	0.0419 (10)	0.0267 (8)	0.0002 (6)	0.0124 (6)	−0.0041 (7)
C20	0.0217 (7)	0.0444 (11)	0.0312 (8)	0.0017 (6)	0.0141 (6)	−0.0102 (7)
C21	0.0233 (7)	0.0345 (10)	0.0379 (9)	0.0020 (6)	0.0117 (7)	−0.0099 (7)
C22	0.0227 (7)	0.0337 (10)	0.0321 (8)	0.0013 (6)	0.0103 (6)	−0.0024 (7)
C23	0.0173 (6)	0.0329 (9)	0.0246 (7)	−0.0006 (6)	0.0084 (6)	−0.0041 (6)
C24	0.0173 (6)	0.0306 (9)	0.0248 (7)	−0.0006 (6)	0.0100 (6)	−0.0011 (6)
C25	0.0218 (7)	0.0288 (9)	0.0246 (7)	0.0022 (6)	0.0111 (6)	0.0031 (6)
C26	0.0278 (7)	0.0336 (10)	0.0255 (7)	0.0010 (6)	0.0152 (6)	0.0004 (6)
C27	0.0242 (7)	0.0338 (10)	0.0311 (8)	0.0006 (6)	0.0160 (6)	0.0013 (6)
C28	0.0237 (7)	0.0283 (9)	0.0277 (8)	0.0012 (6)	0.0104 (6)	0.0015 (6)
C29	0.0319 (8)	0.0380 (10)	0.0238 (8)	0.0063 (7)	0.0128 (7)	0.0005 (6)
C30	0.0269 (7)	0.0419 (10)	0.0253 (8)	0.0082 (7)	0.0146 (6)	0.0024 (7)
C31	0.0292 (8)	0.0309 (10)	0.0299 (8)	−0.0009 (6)	0.0127 (7)	−0.0023 (7)
B1	0.0237 (8)	0.0300 (10)	0.0233 (8)	0.0033 (7)	0.0117 (7)	−0.0013 (7)

O1—C25	1.3593 (16)	C11—C12	1.384 (2)
O1—B1	1.4544 (18)	C11—H11A	0.9500
N1—C1	1.362 (2)	C12—C13	1.393 (2)
N1—C8	1.3718 (18)	C12—H12A	0.9500
N1—B1	1.4995 (19)	C13—C14	1.385 (2)
N2—C8	1.340 (2)	C13—H13A	0.9500
N2—C9	1.3458 (18)	C14—C15	1.394 (2)
N3—C9	1.3706 (18)	C14—H14A	0.9500
N3—C16	1.3744 (18)	C15—C16	1.459 (2)
N3—B1	1.499 (2)	C17—C18	1.452 (2)
N4—C16	1.342 (2)	C18—C19	1.397 (2)
N4—C17	1.348 (2)	C18—C23	1.419 (2)
N5—C24	1.3658 (19)	C19—C20	1.379 (2)
N5—C17	1.3726 (18)	C19—H19A	0.9500
N5—B1	1.496 (2)	C20—C21	1.395 (2)
N6—C24	1.3473 (18)	C20—H20A	0.9500
N6—C1	1.3510 (19)	C21—C22	1.387 (2)
N7—C31	1.1476 (19)	C21—H21A	0.9500
C1—C2	1.4553 (18)	C22—C23	1.389 (2)
C2—C3	1.401 (2)	C22—H22A	0.9500
C2—C7	1.415 (2)	C23—C24	1.450 (2)
C3—C4	1.384 (2)	C25—C30	1.395 (2)
C3—H3A	0.9500	C25—C26	1.398 (2)
C4—C5	1.395 (2)	C26—C27	1.386 (2)
C4—H4A	0.9500	C26—H26A	0.9500
C5—C6	1.380 (2)	C27—C28	1.392 (2)
C5—H5A	0.9500	C27—H27A	0.9500
C6—C7	1.3969 (19)	C28—C29	1.394 (2)
C6—H6A	0.9500	C28—C31	1.440 (2)
C7—C8	1.456 (2)	C29—C30	1.382 (2)
C9—C10	1.455 (2)	C29—H29A	0.9500
C10—C11	1.396 (2)	C30—H30A	0.9500
C10—C15	1.420 (2)
C25—O1—B1	128.89 (11)	C14—C15—C10	120.23 (14)
C1—N1—C8	112.80 (11)	C14—C15—C16	132.36 (15)
C1—N1—B1	122.86 (12)	C10—C15—C16	107.11 (13)
C8—N1—B1	122.55 (13)	N4—C16—N3	122.43 (14)
C8—N2—C9	117.12 (12)	N4—C16—C15	129.92 (14)
C9—N3—C16	112.27 (12)	N3—C16—C15	105.78 (13)
C9—N3—B1	122.45 (12)	N4—C17—N5	122.68 (13)
C16—N3—B1	123.54 (12)	N4—C17—C18	130.99 (13)
C16—N4—C17	117.12 (13)	N5—C17—C18	105.44 (13)
C24—N5—C17	112.54 (12)	C19—C18—C23	120.65 (15)
C24—N5—B1	122.79 (12)	C19—C18—C17	131.87 (15)
C17—N5—B1	123.46 (13)	C23—C18—C17	107.41 (12)
C24—N6—C1	116.35 (13)	C20—C19—C18	117.58 (15)
N6—C1—N1	123.02 (12)	C20—C19—H19A	121.2
N6—C1—C2	129.00 (14)	C18—C19—H19A	121.2
N1—C1—C2	106.01 (12)	C19—C20—C21	121.86 (14)
C3—C2—C7	120.47 (13)	C19—C20—H20A	119.1
C3—C2—C1	131.80 (14)	C21—C20—H20A	119.1
C7—C2—C1	107.24 (13)	C22—C21—C20	121.19 (16)
C4—C3—C2	117.71 (15)	C22—C21—H21A	119.4
C4—C3—H3A	121.1	C20—C21—H21A	119.4
C2—C3—H3A	121.1	C21—C22—C23	117.89 (15)
C3—C4—C5	121.48 (15)	C21—C22—H22A	121.1
C3—C4—H4A	119.3	C23—C22—H22A	121.1
C5—C4—H4A	119.3	C22—C23—C18	120.72 (13)
C6—C5—C4	121.73 (14)	C22—C23—C24	132.25 (14)
C6—C5—H5A	119.1	C18—C23—C24	106.98 (14)
C4—C5—H5A	119.1	N6—C24—N5	122.53 (13)
C5—C6—C7	117.60 (15)	N6—C24—C23	129.70 (14)
C5—C6—H6A	121.2	N5—C24—C23	105.88 (12)
C7—C6—H6A	121.2	O1—C25—C30	124.84 (13)
C6—C7—C2	120.97 (13)	O1—C25—C26	115.73 (12)
C6—C7—C8	131.24 (15)	C30—C25—C26	119.42 (13)
C2—C7—C8	107.23 (12)	C27—C26—C25	120.06 (13)
N2—C8—N1	123.06 (13)	C27—C26—H26A	120.0
N2—C8—C7	129.22 (13)	C25—C26—H26A	120.0
N1—C8—C7	105.76 (13)	C26—C27—C28	120.29 (14)
N2—C9—N3	122.72 (14)	C26—C27—H27A	119.9
N2—C9—C10	128.97 (13)	C28—C27—H27A	119.9
N3—C9—C10	106.04 (12)	C27—C28—C29	119.60 (13)
C11—C10—C15	120.73 (14)	C27—C28—C31	120.48 (13)
C11—C10—C9	131.58 (14)	C29—C28—C31	119.91 (14)
C15—C10—C9	107.20 (13)	C30—C29—C28	120.25 (14)
C12—C11—C10	117.94 (15)	C30—C29—H29A	119.9
C12—C11—H11A	121.0	C28—C29—H29A	119.9
C10—C11—H11A	121.0	C29—C30—C25	120.32 (14)
C11—C12—C13	121.46 (16)	C29—C30—H30A	119.8
C11—C12—H12A	119.3	C25—C30—H30A	119.8
C13—C12—H12A	119.3	N7—C31—C28	179.29 (19)
C14—C13—C12	121.33 (16)	O1—B1—N5	117.99 (12)
C14—C13—H13A	119.3	O1—B1—N3	116.79 (13)
C12—C13—H13A	119.3	N5—B1—N3	104.14 (12)
C13—C14—C15	118.27 (15)	O1—B1—N1	107.91 (12)
C13—C14—H14A	120.9	N5—B1—N1	103.72 (12)
C15—C14—H14A	120.9	N3—B1—N1	104.83 (12)

Cg1, Cg2 and Cg3 are the centroids of the C25–C30, N1/C1/C2/C7/C8 and N3/C9/C10/C15/C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg1i	0.95	2.70	3.499 (3)	143
C20—H20A···Cg2ii	0.95	2.59	3.254 (4)	127
C21—H21A···Cg3ii	0.95	2.70	3.238 (4)	116

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C25–C30, N1/C1/C2/C7/C8 and N3/C9/C10/C15/C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg1i	0.95	2.70	3.499 (3)	143
C20—H20A⋯Cg2ii	0.95	2.59	3.254 (4)	127
C21—H21A⋯Cg3ii	0.95	2.70	3.238 (4)	116

Symmetry codes: (i) ; (ii) .