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

The main feature of the structure of the title compound, C(30)H(16)BN(7)O(3) or NO(2)PhO-BsubPc, are pairs of mol-ecules linked through π-inter-actions between the concave faces of the BsubPc fragments at a distance of 3.5430 (11) Å across an inversion centre. However, the angle between the planes of the five- and six-menbered rings involved in this inter-action is 1.44 (10)°, causing the inter-acting BsubPcs units to be slightly askew rather than parallel as is typical for π-stacking inter-actions.

Related literature

For a general review of boronsubphthalocyanine compounds (BsubPcs), see: Claessens et al. (2002 ▶). For synthesis of BsubPcs and their derivatives, see: Zyskowski & Kennedy (2000 ▶); Claessens et al. (2003 ▶); Paton et al. (2010 ▶). For the application of BsubPcs in organic electronic devices, see: Morse et al. (2010 ▶) and references cited therein; Gommans et al. (2007 ▶). For related structures of non-halogenated BsubPc derivatives, see: Potz et al. (2000 ▶); Paton et al. (2010a ▶,b ▶).

Experimental

Crystal data

C30H16BN7O3

M = 533.31

Monoclinic,

a = 15.6597 (4) Å

b = 8.2959 (1) Å

c = 19.5409 (5) Å

β = 110.3060 (9)°

V = 2380.82 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 150 K

0.40 × 0.26 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.786, T max = 1.000

19982 measured reflections

5413 independent reflections

3646 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.141

S = 1.03

5413 reflections

371 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.33 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/S1600536810050580/nc2204sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050580/nc2204Isup2.hkl

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

C30H16BN7O3	F(000) = 1096
Mr = 533.31	Dx = 1.488 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19982 reflections
a = 15.6597 (4) Å	θ = 2.7–27.5°
b = 8.2959 (1) Å	µ = 0.10 mm−1
c = 19.5409 (5) Å	T = 150 K
β = 110.3060 (9)°	Needle, purple
V = 2380.82 (9) Å3	0.40 × 0.26 × 0.20 mm
Z = 4

Nonius KappaCCD diffractometer	5413 independent reflections
Radiation source: fine-focus sealed tube	3646 reflections with I > 2σ(I)
graphite	Rint = 0.052
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.7°
φ scans and ω scans with κ offsets	h = −20→20
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −10→10
Tmin = 0.788, Tmax = 1.002	l = −20→25
19982 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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0779P)2 + 0.3383P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
5413 reflections	Δρmax = 0.27 e Å−3
371 parameters	Δρmin = −0.33 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: 0.0062 (13)

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	0.16074 (8)	0.41514 (14)	0.53315 (7)	0.0317 (3)
O2	0.02540 (12)	1.06889 (18)	0.61544 (8)	0.0608 (5)
O3	0.15045 (11)	1.04404 (18)	0.70707 (8)	0.0506 (4)
N1	0.23549 (10)	0.23375 (17)	0.47826 (8)	0.0264 (3)
N2	0.27422 (10)	0.41366 (17)	0.39899 (8)	0.0280 (3)
N3	0.31349 (10)	0.47425 (16)	0.52541 (8)	0.0257 (3)
N4	0.41782 (10)	0.47197 (17)	0.64801 (8)	0.0278 (4)
N5	0.30600 (10)	0.26475 (17)	0.60546 (8)	0.0264 (3)
N6	0.26077 (10)	0.00320 (18)	0.55444 (8)	0.0295 (4)
N7	0.09529 (12)	0.99495 (19)	0.64927 (9)	0.0365 (4)
C1	0.23052 (12)	0.0710 (2)	0.48797 (10)	0.0260 (4)
C2	0.21032 (12)	0.0005 (2)	0.41596 (10)	0.0274 (4)
C3	0.19231 (12)	−0.1576 (2)	0.39047 (10)	0.0307 (4)
H3A	0.1886	−0.2423	0.4221	0.037*
C4	0.18000 (13)	−0.1875 (2)	0.31828 (11)	0.0339 (5)
H4A	0.1664	−0.2940	0.2999	0.041*
C5	0.18705 (14)	−0.0644 (2)	0.27145 (11)	0.0349 (5)
H5A	0.1789	−0.0893	0.2221	0.042*
C6	0.20568 (12)	0.0928 (2)	0.29572 (10)	0.0314 (4)
H6A	0.2113	0.1756	0.2639	0.038*
C7	0.21605 (12)	0.1264 (2)	0.36818 (10)	0.0279 (4)
C8	0.23789 (12)	0.2738 (2)	0.41126 (10)	0.0267 (4)
C9	0.31727 (12)	0.5053 (2)	0.45789 (10)	0.0268 (4)
C10	0.38989 (12)	0.6226 (2)	0.46887 (10)	0.0285 (4)
C11	0.42434 (13)	0.6997 (2)	0.42060 (11)	0.0326 (4)
H11A	0.3973	0.6845	0.3694	0.039*
C12	0.49891 (14)	0.7987 (2)	0.44965 (11)	0.0349 (5)
H12A	0.5225	0.8544	0.4176	0.042*
C13	0.54074 (13)	0.8193 (2)	0.52464 (11)	0.0331 (5)
H13A	0.5921	0.8885	0.5425	0.040*
C14	0.50902 (12)	0.7412 (2)	0.57373 (10)	0.0308 (4)
H14A	0.5383	0.7540	0.6249	0.037*
C15	0.43269 (12)	0.6432 (2)	0.54535 (10)	0.0283 (4)
C16	0.38688 (12)	0.5356 (2)	0.58077 (10)	0.0276 (4)
C17	0.38092 (12)	0.3310 (2)	0.65744 (9)	0.0268 (4)
C18	0.42053 (12)	0.2038 (2)	0.70988 (9)	0.0274 (4)
C19	0.49496 (12)	0.2021 (2)	0.77467 (10)	0.0317 (4)
H19A	0.5284	0.2977	0.7932	0.038*
C20	0.51877 (13)	0.0575 (2)	0.81119 (11)	0.0384 (5)
H20A	0.5679	0.0548	0.8565	0.046*
C21	0.47226 (13)	−0.0857 (2)	0.78312 (11)	0.0384 (5)
H21A	0.4902	−0.1832	0.8097	0.046*
C22	0.40048 (13)	−0.0871 (2)	0.71720 (10)	0.0341 (4)
H22A	0.3709	−0.1850	0.6971	0.041*
C23	0.37281 (12)	0.0595 (2)	0.68102 (10)	0.0282 (4)
C24	0.30390 (12)	0.0996 (2)	0.61117 (10)	0.0275 (4)
C25	0.14725 (12)	0.5556 (2)	0.56414 (10)	0.0273 (4)
C26	0.19917 (12)	0.6002 (2)	0.63496 (10)	0.0307 (4)
H26A	0.2461	0.5311	0.6640	0.037*
C27	0.18261 (12)	0.7450 (2)	0.66318 (10)	0.0302 (4)
H27A	0.2188	0.7774	0.7111	0.036*
C28	0.11247 (13)	0.8418 (2)	0.62041 (10)	0.0290 (4)
C29	0.05805 (13)	0.7966 (2)	0.55091 (10)	0.0322 (4)
H29A	0.0088	0.8630	0.5232	0.039*
C30	0.07611 (12)	0.6538 (2)	0.52219 (10)	0.0299 (4)
H30A	0.0402	0.6226	0.4740	0.036*
B1	0.24932 (14)	0.3530 (2)	0.53782 (11)	0.0264 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0254 (7)	0.0321 (7)	0.0366 (8)	0.0012 (5)	0.0094 (6)	−0.0069 (6)
O2	0.0690 (12)	0.0495 (9)	0.0467 (10)	0.0283 (8)	−0.0017 (9)	−0.0077 (7)
O3	0.0539 (10)	0.0491 (9)	0.0383 (9)	0.0037 (7)	0.0027 (8)	−0.0168 (7)
N1	0.0260 (8)	0.0272 (8)	0.0251 (8)	0.0008 (6)	0.0077 (6)	0.0006 (6)
N2	0.0279 (8)	0.0262 (8)	0.0267 (8)	0.0025 (6)	0.0054 (7)	0.0022 (6)
N3	0.0253 (8)	0.0254 (7)	0.0246 (8)	0.0018 (6)	0.0065 (6)	−0.0008 (6)
N4	0.0277 (8)	0.0296 (8)	0.0261 (9)	0.0004 (6)	0.0091 (7)	−0.0016 (6)
N5	0.0250 (8)	0.0296 (8)	0.0246 (8)	0.0006 (6)	0.0088 (6)	0.0011 (6)
N6	0.0261 (8)	0.0330 (8)	0.0297 (9)	−0.0038 (6)	0.0099 (7)	0.0015 (7)
N7	0.0424 (10)	0.0367 (9)	0.0281 (9)	0.0037 (8)	0.0092 (8)	−0.0025 (7)
C1	0.0226 (9)	0.0270 (9)	0.0283 (10)	−0.0004 (7)	0.0089 (8)	0.0015 (7)
C2	0.0221 (9)	0.0315 (9)	0.0272 (10)	0.0012 (7)	0.0069 (8)	−0.0008 (7)
C3	0.0276 (10)	0.0292 (9)	0.0348 (11)	−0.0003 (7)	0.0102 (8)	−0.0017 (8)
C4	0.0315 (11)	0.0316 (10)	0.0377 (12)	−0.0021 (8)	0.0111 (9)	−0.0075 (8)
C5	0.0362 (11)	0.0378 (11)	0.0300 (11)	0.0006 (8)	0.0108 (9)	−0.0065 (8)
C6	0.0297 (10)	0.0355 (10)	0.0283 (10)	0.0004 (8)	0.0092 (8)	0.0012 (8)
C7	0.0223 (9)	0.0304 (9)	0.0289 (10)	0.0003 (7)	0.0061 (8)	−0.0015 (7)
C8	0.0233 (9)	0.0299 (9)	0.0257 (10)	0.0034 (7)	0.0068 (7)	0.0018 (7)
C9	0.0281 (10)	0.0253 (9)	0.0257 (10)	0.0046 (7)	0.0078 (8)	0.0025 (7)
C10	0.0281 (10)	0.0241 (9)	0.0326 (11)	0.0047 (7)	0.0098 (8)	0.0009 (7)
C11	0.0362 (11)	0.0266 (9)	0.0360 (11)	0.0059 (8)	0.0138 (9)	0.0027 (8)
C12	0.0379 (11)	0.0272 (9)	0.0453 (13)	0.0038 (8)	0.0217 (10)	0.0032 (8)
C13	0.0266 (10)	0.0249 (9)	0.0487 (13)	0.0017 (7)	0.0143 (9)	−0.0002 (8)
C14	0.0269 (10)	0.0275 (9)	0.0340 (11)	0.0046 (7)	0.0054 (8)	0.0002 (8)
C15	0.0272 (10)	0.0241 (9)	0.0331 (11)	0.0036 (7)	0.0100 (8)	0.0017 (7)
C16	0.0260 (10)	0.0261 (9)	0.0294 (10)	0.0019 (7)	0.0079 (8)	−0.0033 (7)
C17	0.0226 (9)	0.0333 (10)	0.0244 (10)	0.0003 (7)	0.0078 (8)	−0.0025 (7)
C18	0.0255 (10)	0.0343 (10)	0.0244 (10)	0.0007 (7)	0.0113 (8)	0.0020 (7)
C19	0.0259 (10)	0.0403 (11)	0.0291 (10)	−0.0021 (8)	0.0098 (8)	−0.0005 (8)
C20	0.0278 (11)	0.0491 (12)	0.0335 (11)	−0.0006 (8)	0.0047 (9)	0.0086 (9)
C21	0.0299 (11)	0.0423 (11)	0.0404 (12)	0.0019 (8)	0.0089 (9)	0.0132 (9)
C22	0.0303 (11)	0.0374 (10)	0.0351 (11)	−0.0002 (8)	0.0121 (9)	0.0063 (8)
C23	0.0269 (10)	0.0340 (10)	0.0262 (10)	0.0001 (7)	0.0121 (8)	0.0035 (8)
C24	0.0268 (10)	0.0297 (9)	0.0285 (10)	−0.0015 (7)	0.0128 (8)	0.0015 (7)
C25	0.0259 (10)	0.0288 (9)	0.0293 (10)	−0.0010 (7)	0.0124 (8)	−0.0014 (7)
C26	0.0239 (10)	0.0403 (10)	0.0260 (10)	0.0039 (8)	0.0061 (8)	0.0000 (8)
C27	0.0261 (10)	0.0400 (10)	0.0247 (10)	−0.0016 (8)	0.0090 (8)	−0.0022 (8)
C28	0.0316 (10)	0.0306 (9)	0.0267 (10)	−0.0023 (7)	0.0125 (8)	−0.0019 (7)
C29	0.0331 (11)	0.0326 (10)	0.0273 (10)	0.0020 (8)	0.0061 (8)	0.0013 (8)
C30	0.0302 (10)	0.0330 (10)	0.0244 (10)	0.0001 (8)	0.0068 (8)	−0.0006 (8)
B1	0.0245 (11)	0.0280 (10)	0.0264 (11)	0.0012 (8)	0.0084 (9)	−0.0008 (8)

O1—C25	1.363 (2)	C10—C11	1.394 (3)
O1—B1	1.453 (2)	C10—C15	1.420 (3)
O2—N7	1.228 (2)	C11—C12	1.378 (3)
O3—N7	1.229 (2)	C11—H11A	0.9500
N1—C8	1.364 (2)	C12—C13	1.393 (3)
N1—C1	1.369 (2)	C12—H12A	0.9500
N1—B1	1.485 (2)	C13—C14	1.385 (3)
N2—C9	1.349 (2)	C13—H13A	0.9500
N2—C8	1.350 (2)	C14—C15	1.392 (3)
N3—C9	1.365 (2)	C14—H14A	0.9500
N3—C16	1.374 (2)	C15—C16	1.461 (3)
N3—B1	1.500 (2)	C17—C18	1.451 (2)
N4—C16	1.341 (2)	C18—C19	1.392 (3)
N4—C17	1.345 (2)	C18—C23	1.421 (3)
N5—C17	1.372 (2)	C19—C20	1.379 (3)
N5—C24	1.376 (2)	C19—H19A	0.9500
N5—B1	1.502 (2)	C20—C21	1.401 (3)
N6—C1	1.342 (2)	C20—H20A	0.9500
N6—C24	1.344 (2)	C21—C22	1.385 (3)
N7—C28	1.453 (2)	C21—H21A	0.9500
C1—C2	1.454 (2)	C22—C23	1.398 (3)
C2—C3	1.397 (2)	C22—H22A	0.9500
C2—C7	1.424 (2)	C23—C24	1.455 (3)
C3—C4	1.378 (3)	C25—C26	1.390 (2)
C3—H3A	0.9500	C25—C30	1.394 (2)
C4—C5	1.401 (3)	C26—C27	1.383 (3)
C4—H4A	0.9500	C26—H26A	0.9500
C5—C6	1.383 (3)	C27—C28	1.383 (3)
C5—H5A	0.9500	C27—H27A	0.9500
C6—C7	1.396 (2)	C28—C29	1.381 (3)
C6—H6A	0.9500	C29—C30	1.382 (2)
C7—C8	1.457 (2)	C29—H29A	0.9500
C9—C10	1.455 (3)	C30—H30A	0.9500
C25—O1—B1	124.58 (14)	C13—C14—H14A	121.2
C8—N1—C1	113.27 (14)	C15—C14—H14A	121.2
C8—N1—B1	123.03 (15)	C14—C15—C10	121.07 (17)
C1—N1—B1	123.23 (15)	C14—C15—C16	131.53 (17)
C9—N2—C8	116.73 (15)	C10—C15—C16	107.15 (15)
C9—N3—C16	112.71 (15)	N4—C16—N3	123.03 (16)
C9—N3—B1	122.61 (15)	N4—C16—C15	129.40 (16)
C16—N3—B1	123.05 (15)	N3—C16—C15	105.50 (15)
C16—N4—C17	116.75 (15)	N4—C17—N5	122.97 (16)
C17—N5—C24	112.15 (15)	N4—C17—C18	129.05 (16)
C17—N5—B1	123.28 (15)	N5—C17—C18	106.13 (15)
C24—N5—B1	122.21 (15)	C19—C18—C23	120.77 (16)
C1—N6—C24	117.15 (15)	C19—C18—C17	131.87 (16)
O2—N7—O3	122.68 (17)	C23—C18—C17	107.18 (15)
O2—N7—C28	118.57 (16)	C20—C19—C18	118.05 (17)
O3—N7—C28	118.74 (16)	C20—C19—H19A	121.0
N6—C1—N1	121.98 (16)	C18—C19—H19A	121.0
N6—C1—C2	130.79 (16)	C19—C20—C21	121.60 (19)
N1—C1—C2	105.44 (15)	C19—C20—H20A	119.2
C3—C2—C7	120.36 (17)	C21—C20—H20A	119.2
C3—C2—C1	132.24 (17)	C22—C21—C20	121.01 (18)
C7—C2—C1	107.32 (15)	C22—C21—H21A	119.5
C4—C3—C2	118.25 (17)	C20—C21—H21A	119.5
C4—C3—H3A	120.9	C21—C22—C23	118.17 (18)
C2—C3—H3A	120.9	C21—C22—H22A	120.9
C3—C4—C5	121.49 (17)	C23—C22—H22A	120.9
C3—C4—H4A	119.3	C22—C23—C18	120.29 (17)
C5—C4—H4A	119.3	C22—C23—C24	132.28 (17)
C6—C5—C4	121.21 (18)	C18—C23—C24	107.23 (15)
C6—C5—H5A	119.4	N6—C24—N5	123.04 (16)
C4—C5—H5A	119.4	N6—C24—C23	129.39 (16)
C5—C6—C7	118.18 (17)	N5—C24—C23	105.86 (15)
C5—C6—H6A	120.9	O1—C25—C26	122.87 (16)
C7—C6—H6A	120.9	O1—C25—C30	116.98 (16)
C6—C7—C2	120.47 (16)	C26—C25—C30	120.12 (16)
C6—C7—C8	132.45 (17)	C27—C26—C25	120.16 (17)
C2—C7—C8	106.99 (15)	C27—C26—H26A	119.9
N2—C8—N1	122.25 (16)	C25—C26—H26A	119.9
N2—C8—C7	130.40 (16)	C28—C27—C26	118.85 (17)
N1—C8—C7	105.73 (14)	C28—C27—H27A	120.6
N2—C9—N3	122.80 (16)	C26—C27—H27A	120.6
N2—C9—C10	129.53 (17)	C29—C28—C27	121.77 (17)
N3—C9—C10	106.11 (15)	C29—C28—N7	118.99 (16)
C11—C10—C15	120.32 (17)	C27—C28—N7	119.24 (16)
C11—C10—C9	132.33 (17)	C28—C29—C30	119.24 (17)
C15—C10—C9	107.16 (15)	C28—C29—H29A	120.4
C12—C11—C10	117.79 (18)	C30—C29—H29A	120.4
C12—C11—H11A	121.1	C29—C30—C25	119.78 (17)
C10—C11—H11A	121.1	C29—C30—H30A	120.1
C11—C12—C13	121.91 (18)	C25—C30—H30A	120.1
C11—C12—H12A	119.0	O1—B1—N1	108.11 (15)
C13—C12—H12A	119.0	O1—B1—N3	115.48 (15)
C14—C13—C12	121.35 (18)	N1—B1—N3	104.11 (14)
C14—C13—H13A	119.3	O1—B1—N5	119.21 (15)
C12—C13—H13A	119.3	N1—B1—N5	104.25 (14)
C13—C14—C15	117.54 (17)	N3—B1—N5	104.16 (14)