4,5-Diphen-oxy-benzene-1,2-dicarbo-nitrile.

In the title compound, C(20)H(12)N(2)O(2), the phenyl and benzene rings are mutually perpendicular, with the dihedral angle between the phenyl rings being 87.92 (16)° and those formed between the phenyl rings and the benzene rings being 73.68 (15) and 84.65 (15)°. Helical supra-molecular chains along [010], mediated by C-H⋯N inter-actions, are found in the crystal structure.

Related literature

For the use of functionalized phthalocyanines as dyes in photodynamic therapy and in dye-sensitized solar cells, see: Li et al. (2008 ▶); Jiang et al. (2011 ▶); Zhao et al. (2009 ▶). For a related structure, see: Yu et al. (2010 ▶). The present synthesis is based on earlier syntheses; see: Wohrle et al. (1993 ▶); Li et al. (2008 ▶).

Experimental

Crystal data

C20H12N2O2

M = 312.32

Orthorhombic,

a = 5.6543 (4) Å

b = 13.5163 (9) Å

c = 19.9498 (17) Å

V = 1524.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.10 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.974, T max = 0.991

4325 measured reflections

2029 independent reflections

1498 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.118

S = 1.01

2029 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004060/hg5172sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004060/hg5172Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004060/hg5172Isup3.cml

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

C20H12N2O2	F(000) = 648
Mr = 312.32	Dx = 1.361 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1267 reflections
a = 5.6543 (4) Å	θ = 2.5–27.5°
b = 13.5163 (9) Å	µ = 0.09 mm−1
c = 19.9498 (17) Å	T = 100 K
V = 1524.7 (2) Å3	Block, colourless
Z = 4	0.30 × 0.10 × 0.10 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	2029 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1498 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.052
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.5°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −17→16
Tmin = 0.974, Tmax = 0.991	l = −25→17
4325 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0522P)2] where P = (Fo2 + 2Fc2)/3
2029 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.7480 (4)	0.46056 (17)	0.21758 (11)	0.0246 (5)
O2	0.8019 (4)	0.49051 (16)	0.08401 (11)	0.0237 (6)
N1	1.6503 (5)	0.2459 (2)	0.05129 (14)	0.0276 (7)
N2	1.5732 (5)	0.1975 (2)	0.24912 (15)	0.0302 (7)
C1	0.9365 (6)	0.4161 (2)	0.18642 (16)	0.0205 (7)
C2	0.9635 (6)	0.4325 (2)	0.11812 (16)	0.0191 (7)
C3	1.1429 (6)	0.3878 (2)	0.08308 (17)	0.0217 (7)
H3	1.1582	0.3992	0.0363	0.026*
C4	1.3028 (6)	0.3257 (2)	0.11572 (16)	0.0215 (8)
C5	1.2763 (6)	0.3093 (2)	0.18456 (16)	0.0197 (7)
C6	1.0916 (6)	0.3539 (2)	0.21997 (17)	0.0196 (7)
H6	1.0724	0.3417	0.2665	0.024*
C7	1.4946 (6)	0.2810 (2)	0.07954 (16)	0.0218 (7)
C8	1.4418 (6)	0.2465 (2)	0.22039 (16)	0.0220 (7)
C9	0.7792 (6)	0.4909 (2)	0.28421 (16)	0.0210 (7)
C10	0.6053 (6)	0.4644 (3)	0.32990 (17)	0.0262 (8)
H10	0.4760	0.4240	0.3168	0.031*
C11	0.6253 (6)	0.4987 (3)	0.39549 (17)	0.0272 (8)
H11	0.5082	0.4813	0.4275	0.033*
C12	0.8137 (6)	0.5579 (2)	0.41466 (18)	0.0288 (8)
H12	0.8254	0.5810	0.4595	0.035*
C13	0.9840 (6)	0.5829 (2)	0.36819 (17)	0.0271 (8)
H13	1.1136	0.6233	0.3812	0.033*
C14	0.9673 (6)	0.5493 (2)	0.30229 (17)	0.0248 (8)
H14	1.0848	0.5665	0.2703	0.030*
C15	0.8279 (5)	0.5936 (2)	0.08943 (16)	0.0200 (7)
C16	1.0254 (6)	0.6379 (2)	0.11785 (16)	0.0220 (8)
H16	1.1490	0.5989	0.1363	0.026*
C17	1.0384 (6)	0.7406 (3)	0.11868 (16)	0.0244 (8)
H17	1.1726	0.7720	0.1378	0.029*
C18	0.8576 (6)	0.7979 (2)	0.09186 (16)	0.0251 (8)
H18	0.8667	0.8681	0.0932	0.030*
C19	0.6632 (6)	0.7514 (3)	0.06305 (16)	0.0253 (8)
H19	0.5397	0.7901	0.0441	0.030*
C20	0.6483 (6)	0.6491 (2)	0.06170 (16)	0.0233 (8)
H20	0.5156	0.6176	0.0419	0.028*

	U11	U22	U33	U12	U13	U23
O1	0.0196 (12)	0.0316 (12)	0.0227 (12)	0.0066 (12)	−0.0010 (10)	−0.0033 (10)
O2	0.0241 (14)	0.0174 (10)	0.0296 (13)	0.0020 (10)	−0.0070 (11)	0.0005 (10)
N1	0.0256 (16)	0.0299 (15)	0.0274 (16)	0.0015 (15)	−0.0001 (14)	−0.0008 (14)
N2	0.0240 (16)	0.0299 (15)	0.0366 (18)	0.0041 (15)	−0.0025 (15)	−0.0008 (14)
C1	0.0182 (16)	0.0166 (14)	0.0267 (19)	−0.0032 (15)	0.0007 (15)	−0.0060 (14)
C2	0.0161 (16)	0.0157 (15)	0.0255 (18)	−0.0002 (14)	−0.0055 (14)	−0.0027 (13)
C3	0.0236 (17)	0.0170 (14)	0.0246 (19)	−0.0017 (14)	−0.0005 (16)	−0.0020 (14)
C4	0.0219 (19)	0.0172 (16)	0.0254 (19)	−0.0014 (15)	0.0000 (15)	−0.0032 (14)
C5	0.0182 (16)	0.0132 (13)	0.0277 (18)	−0.0023 (14)	−0.0042 (15)	−0.0018 (14)
C6	0.0185 (17)	0.0190 (15)	0.0212 (17)	−0.0001 (15)	0.0012 (14)	0.0002 (14)
C7	0.0223 (18)	0.0209 (16)	0.0221 (18)	−0.0042 (16)	−0.0052 (16)	−0.0001 (14)
C8	0.0223 (17)	0.0192 (15)	0.0244 (18)	−0.0013 (16)	0.0030 (15)	−0.0013 (15)
C9	0.0225 (17)	0.0195 (15)	0.0209 (17)	0.0069 (15)	0.0017 (15)	0.0016 (14)
C10	0.0219 (18)	0.0255 (16)	0.031 (2)	−0.0013 (16)	0.0011 (15)	−0.0034 (16)
C11	0.0280 (19)	0.0240 (16)	0.030 (2)	0.0015 (17)	0.0061 (16)	0.0008 (16)
C12	0.035 (2)	0.0262 (18)	0.0253 (19)	0.0079 (17)	−0.0027 (17)	−0.0064 (16)
C13	0.0254 (18)	0.0221 (16)	0.034 (2)	0.0034 (16)	−0.0046 (17)	−0.0058 (15)
C14	0.0188 (16)	0.0203 (16)	0.035 (2)	0.0042 (16)	0.0042 (16)	0.0031 (15)
C15	0.0190 (17)	0.0199 (15)	0.0211 (18)	−0.0016 (15)	0.0027 (15)	−0.0010 (14)
C16	0.0185 (17)	0.0266 (17)	0.0209 (18)	0.0024 (16)	−0.0008 (15)	0.0003 (14)
C17	0.0206 (17)	0.0314 (17)	0.0212 (18)	−0.0053 (17)	0.0007 (15)	−0.0061 (16)
C18	0.0245 (18)	0.0219 (16)	0.0289 (19)	0.0027 (16)	0.0057 (16)	−0.0005 (15)
C19	0.0246 (18)	0.0263 (17)	0.0250 (18)	0.0078 (16)	−0.0004 (15)	0.0026 (16)
C20	0.0172 (16)	0.0293 (17)	0.0232 (18)	0.0014 (16)	0.0004 (15)	0.0002 (15)

O1—C1	1.373 (4)	C10—H10	0.9500
O1—C9	1.402 (4)	C11—C12	1.386 (5)
O2—C2	1.383 (4)	C11—H11	0.9500
O2—C15	1.405 (3)	C12—C13	1.379 (5)
N1—C7	1.148 (4)	C12—H12	0.9500
N2—C8	1.148 (4)	C13—C14	1.394 (5)
C1—C6	1.387 (4)	C13—H13	0.9500
C1—C2	1.389 (4)	C14—H14	0.9500
C2—C3	1.372 (4)	C15—C20	1.379 (4)
C3—C4	1.395 (4)	C15—C16	1.388 (4)
C3—H3	0.9500	C16—C17	1.390 (4)
C4—C5	1.399 (4)	C16—H16	0.9500
C4—C7	1.436 (5)	C17—C18	1.390 (5)
C5—C6	1.398 (5)	C17—H17	0.9500
C5—C8	1.452 (5)	C18—C19	1.391 (5)
C6—H6	0.9500	C18—H18	0.9500
C9—C14	1.372 (5)	C19—C20	1.385 (4)
C9—C10	1.388 (5)	C19—H19	0.9500
C10—C11	1.393 (5)	C20—H20	0.9500
C1—O1—C9	117.4 (2)	C12—C11—H11	119.5
C2—O2—C15	117.1 (2)	C10—C11—H11	119.5
O1—C1—C6	122.5 (3)	C13—C12—C11	119.5 (3)
O1—C1—C2	117.4 (3)	C13—C12—H12	120.2
C6—C1—C2	120.1 (3)	C11—C12—H12	120.2
C3—C2—O2	119.2 (3)	C12—C13—C14	120.4 (3)
C3—C2—C1	120.7 (3)	C12—C13—H13	119.8
O2—C2—C1	120.1 (3)	C14—C13—H13	119.8
C2—C3—C4	120.4 (3)	C9—C14—C13	119.2 (3)
C2—C3—H3	119.8	C9—C14—H14	120.4
C4—C3—H3	119.8	C13—C14—H14	120.4
C3—C4—C5	119.0 (3)	C20—C15—C16	121.4 (3)
C3—C4—C7	120.5 (3)	C20—C15—O2	115.6 (3)
C5—C4—C7	120.5 (3)	C16—C15—O2	122.9 (3)
C6—C5—C4	120.5 (3)	C15—C16—C17	118.6 (3)
C6—C5—C8	119.0 (3)	C15—C16—H16	120.7
C4—C5—C8	120.5 (3)	C17—C16—H16	120.7
C1—C6—C5	119.3 (3)	C18—C17—C16	120.9 (3)
C1—C6—H6	120.3	C18—C17—H17	119.6
C5—C6—H6	120.3	C16—C17—H17	119.6
N1—C7—C4	178.9 (3)	C17—C18—C19	119.2 (3)
N2—C8—C5	179.4 (4)	C17—C18—H18	120.4
C14—C9—C10	121.7 (3)	C19—C18—H18	120.4
C14—C9—O1	121.0 (3)	C20—C19—C18	120.5 (3)
C10—C9—O1	117.2 (3)	C20—C19—H19	119.8
C9—C10—C11	118.3 (3)	C18—C19—H19	119.8
C9—C10—H10	120.9	C15—C20—C19	119.4 (3)
C11—C10—H10	120.9	C15—C20—H20	120.3
C12—C11—C10	120.9 (3)	C19—C20—H20	120.3
C9—O1—C1—C6	35.9 (4)	C6—C5—C8—N2	−55 (41)
C9—O1—C1—C2	−146.5 (3)	C4—C5—C8—N2	124 (41)
C15—O2—C2—C3	−103.2 (3)	C1—O1—C9—C14	52.0 (4)
C15—O2—C2—C1	80.0 (4)	C1—O1—C9—C10	−131.6 (3)
O1—C1—C2—C3	−177.7 (3)	C14—C9—C10—C11	0.1 (5)
C6—C1—C2—C3	0.0 (4)	O1—C9—C10—C11	−176.3 (3)
O1—C1—C2—O2	−1.0 (4)	C9—C10—C11—C12	0.1 (5)
C6—C1—C2—O2	176.7 (3)	C10—C11—C12—C13	−0.2 (5)
O2—C2—C3—C4	−177.4 (3)	C11—C12—C13—C14	0.1 (5)
C1—C2—C3—C4	−0.7 (5)	C10—C9—C14—C13	−0.1 (5)
C2—C3—C4—C5	0.5 (5)	O1—C9—C14—C13	176.1 (3)
C2—C3—C4—C7	−178.3 (3)	C12—C13—C14—C9	0.0 (5)
C3—C4—C5—C6	0.4 (5)	C2—O2—C15—C20	−172.5 (3)
C7—C4—C5—C6	179.1 (3)	C2—O2—C15—C16	10.5 (4)
C3—C4—C5—C8	−179.0 (3)	C20—C15—C16—C17	0.8 (5)
C7—C4—C5—C8	−0.2 (5)	O2—C15—C16—C17	177.7 (3)
O1—C1—C6—C5	178.4 (3)	C15—C16—C17—C18	0.2 (5)
C2—C1—C6—C5	0.9 (4)	C16—C17—C18—C19	−0.9 (5)
C4—C5—C6—C1	−1.1 (5)	C17—C18—C19—C20	0.7 (5)
C8—C5—C6—C1	178.3 (3)	C16—C15—C20—C19	−1.0 (5)
C3—C4—C7—N1	123 (21)	O2—C15—C20—C19	−178.1 (3)
C5—C4—C7—N1	−56 (21)	C18—C19—C20—C15	0.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N1i	0.95	2.52	3.422 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N1i	0.95	2.52	3.422 (4)	159

Symmetry code: (i) .