4,5-Bis(4-meth-oxy-phen-oxy)phthalonitrile.

The title compound, C(22)H(16)N(2)O(4), was obtained unintentionally as the product of an attempted synthesis of a new phthalocyanine. The dihedral angles formed by the central benzene ring with the aromatic rings of the meth-oxy-phen-oxy groups are 85.39 (5) and 64.19 (5)°.

Related literature

For background information on phthalcoyanines, see: Hanack & Lang (1994 ▶). For the synthesis of the title compound, see: Li et al. (2006 ▶).

Experimental

Crystal data

C22H16N2O4

M = 372.37

Monoclinic,

a = 13.7614 (2) Å

b = 10.4926 (1) Å

c = 14.0701 (2) Å

β = 112.551 (1)°

V = 1876.28 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.38 × 0.23 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.966, T max = 0.988

24018 measured reflections

3311 independent reflections

2189 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 1.02

3311 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035610/rz2481sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035610/rz2481Isup2.hkl

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

C22H16N2O4	F(000) = 776
Mr = 372.37	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5549 reflections
a = 13.7614 (2) Å	θ = 2.5–23.5°
b = 10.4926 (1) Å	µ = 0.09 mm−1
c = 14.0701 (2) Å	T = 298 K
β = 112.551 (1)°	Block, colourless
V = 1876.28 (4) Å3	0.38 × 0.23 × 0.13 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3311 independent reflections
Radiation source: fine-focus sealed tube	2189 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scan	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −16→16
Tmin = 0.966, Tmax = 0.988	k = −11→12
24018 measured reflections	l = −16→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0369P)2 + 0.4099P] where P = (Fo2 + 2Fc2)/3
3311 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.17 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
C17	0.07245 (13)	0.02765 (18)	0.29042 (13)	0.0566 (5)
H17	0.0524	0.1096	0.2653	0.068*
N2	0.54537 (15)	0.17422 (18)	0.53262 (13)	0.0822 (6)
N1	0.63571 (15)	0.30662 (18)	0.31740 (13)	0.0820 (5)
C2	0.49439 (14)	0.16026 (18)	0.44763 (15)	0.0572 (5)
C1	0.55634 (16)	0.25589 (18)	0.29120 (14)	0.0598 (5)
O1	0.22453 (9)	0.09523 (14)	0.03832 (9)	0.0684 (4)
O2	0.16999 (9)	0.01007 (12)	0.18264 (8)	0.0621 (4)
O3	0.33469 (11)	0.01535 (14)	−0.29526 (10)	0.0796 (4)
O4	0.02251 (11)	−0.19057 (15)	0.46372 (11)	0.0843 (5)
C5	0.33212 (13)	0.08186 (16)	0.31600 (12)	0.0496 (4)
H5	0.3124	0.0507	0.3679	0.060*
C3	0.45763 (13)	0.19033 (16)	0.26340 (13)	0.0494 (4)
C7	0.29686 (13)	0.11161 (17)	0.13679 (12)	0.0510 (4)
C6	0.26639 (13)	0.06676 (16)	0.21448 (12)	0.0485 (4)
C4	0.42795 (13)	0.14356 (16)	0.34096 (12)	0.0475 (4)
C8	0.39146 (13)	0.17408 (16)	0.16126 (13)	0.0534 (5)
H8	0.4109	0.2053	0.1092	0.064*
C9	0.25752 (13)	0.07923 (17)	−0.04349 (12)	0.0513 (4)
C11	0.21973 (15)	0.11325 (19)	−0.22164 (13)	0.0611 (5)
H11	0.1780	0.1501	−0.2841	0.073*
C12	0.30366 (15)	0.03855 (18)	−0.21509 (13)	0.0561 (5)
C10	0.19704 (14)	0.13386 (19)	−0.13506 (13)	0.0599 (5)
H10	0.1404	0.1851	−0.1394	0.072*
C14	0.34035 (16)	0.0024 (2)	−0.03671 (14)	0.0701 (6)
H14	0.3807	−0.0364	0.0253	0.084*
C15	0.25790 (19)	0.0227 (2)	−0.39650 (15)	0.0916 (7)
H15A	0.1982	−0.0284	−0.4017	0.137*
H15B	0.2871	−0.0083	−0.4441	0.137*
H15C	0.2362	0.1097	−0.4125	0.137*
C13	0.36321 (16)	−0.0166 (2)	−0.12246 (15)	0.0729 (6)
H13	0.4200	−0.0679	−0.1177	0.087*
C16	0.13818 (13)	−0.04202 (18)	0.25815 (12)	0.0500 (4)
C19	0.06522 (13)	−0.14685 (19)	0.39663 (13)	0.0562 (5)
C18	0.03643 (14)	−0.02478 (19)	0.36030 (14)	0.0611 (5)
H18	−0.0076	0.0223	0.3832	0.073*
C20	0.13229 (14)	−0.21514 (19)	0.36496 (14)	0.0605 (5)
H20	0.1529	−0.2968	0.3903	0.073*
C21	0.16913 (14)	−0.16199 (19)	0.29513 (14)	0.0610 (5)
H21	0.2148	−0.2077	0.2735	0.073*
C22	0.05311 (19)	−0.3141 (2)	0.50731 (17)	0.0959 (8)
H22A	0.0348	−0.3764	0.4533	0.144*
H22B	0.0174	−0.3333	0.5523	0.144*
H22C	0.1278	−0.3156	0.5457	0.144*

	U11	U22	U33	U12	U13	U23
C17	0.0538 (11)	0.0585 (12)	0.0579 (11)	0.0016 (9)	0.0218 (9)	0.0032 (9)
N2	0.0906 (13)	0.0919 (14)	0.0548 (11)	−0.0179 (11)	0.0175 (10)	−0.0080 (9)
N1	0.0812 (12)	0.0891 (13)	0.0840 (12)	−0.0312 (11)	0.0409 (10)	−0.0140 (10)
C2	0.0604 (11)	0.0590 (12)	0.0547 (12)	−0.0090 (9)	0.0249 (10)	−0.0040 (9)
C1	0.0674 (13)	0.0617 (13)	0.0582 (12)	−0.0135 (11)	0.0330 (10)	−0.0070 (9)
O1	0.0540 (7)	0.1085 (11)	0.0438 (7)	−0.0043 (7)	0.0200 (6)	0.0038 (7)
O2	0.0499 (7)	0.0901 (10)	0.0466 (7)	−0.0137 (7)	0.0187 (6)	0.0044 (6)
O3	0.0843 (10)	0.1044 (12)	0.0543 (8)	0.0018 (8)	0.0311 (7)	−0.0108 (8)
O4	0.0803 (10)	0.1067 (12)	0.0830 (10)	0.0058 (9)	0.0502 (8)	0.0287 (9)
C5	0.0543 (11)	0.0557 (11)	0.0444 (10)	0.0003 (9)	0.0250 (8)	0.0026 (8)
C3	0.0525 (10)	0.0480 (10)	0.0533 (10)	−0.0039 (8)	0.0263 (9)	−0.0024 (8)
C7	0.0521 (10)	0.0591 (11)	0.0427 (10)	0.0022 (9)	0.0193 (8)	0.0028 (8)
C6	0.0453 (10)	0.0532 (11)	0.0495 (10)	−0.0009 (8)	0.0211 (8)	0.0016 (8)
C4	0.0506 (10)	0.0473 (10)	0.0463 (10)	−0.0005 (8)	0.0205 (8)	−0.0028 (8)
C8	0.0591 (11)	0.0591 (12)	0.0502 (10)	−0.0017 (9)	0.0302 (9)	0.0042 (9)
C9	0.0506 (10)	0.0611 (12)	0.0423 (10)	−0.0062 (9)	0.0179 (8)	0.0023 (8)
C11	0.0629 (12)	0.0727 (13)	0.0433 (10)	−0.0001 (10)	0.0155 (9)	0.0107 (9)
C12	0.0610 (12)	0.0617 (12)	0.0463 (10)	−0.0065 (10)	0.0213 (9)	−0.0047 (9)
C10	0.0532 (11)	0.0723 (13)	0.0523 (11)	0.0070 (10)	0.0180 (9)	0.0086 (10)
C14	0.0786 (14)	0.0786 (15)	0.0464 (11)	0.0182 (11)	0.0166 (10)	0.0123 (10)
C15	0.1065 (18)	0.120 (2)	0.0493 (12)	−0.0121 (15)	0.0310 (12)	−0.0134 (12)
C13	0.0765 (14)	0.0812 (15)	0.0571 (12)	0.0228 (11)	0.0213 (11)	−0.0005 (11)
C16	0.0428 (9)	0.0633 (12)	0.0441 (9)	−0.0084 (9)	0.0166 (8)	0.0005 (9)
C19	0.0463 (10)	0.0733 (14)	0.0511 (10)	−0.0036 (10)	0.0211 (9)	0.0057 (10)
C18	0.0558 (11)	0.0723 (14)	0.0632 (12)	0.0069 (10)	0.0316 (10)	0.0005 (10)
C20	0.0590 (11)	0.0601 (12)	0.0620 (12)	0.0040 (10)	0.0229 (10)	0.0087 (10)
C21	0.0575 (11)	0.0706 (14)	0.0613 (11)	0.0063 (10)	0.0298 (9)	−0.0009 (10)
C22	0.0987 (17)	0.113 (2)	0.0784 (15)	−0.0085 (15)	0.0363 (13)	0.0389 (14)

C17—C16	1.369 (2)	C9—C10	1.363 (2)
C17—C18	1.374 (2)	C9—C14	1.369 (2)
C17—H17	0.9300	C11—C12	1.369 (3)
N2—C2	1.140 (2)	C11—C10	1.386 (2)
N1—C1	1.142 (2)	C11—H11	0.9300
C2—C4	1.438 (2)	C12—C13	1.373 (3)
C1—C3	1.437 (3)	C10—H10	0.9300
O1—C7	1.3719 (19)	C14—C13	1.373 (3)
O1—C9	1.400 (2)	C14—H14	0.9300
O2—C6	1.3633 (19)	C15—H15A	0.9600
O2—C16	1.4057 (19)	C15—H15B	0.9600
O3—C12	1.372 (2)	C15—H15C	0.9600
O3—C15	1.413 (2)	C13—H13	0.9300
O4—C19	1.369 (2)	C16—C21	1.366 (2)
O4—C22	1.426 (3)	C19—C20	1.371 (2)
C5—C6	1.376 (2)	C19—C18	1.380 (3)
C5—C4	1.388 (2)	C18—H18	0.9300
C5—H5	0.9300	C20—C21	1.384 (2)
C3—C8	1.386 (2)	C20—H20	0.9300
C3—C4	1.393 (2)	C21—H21	0.9300
C7—C8	1.378 (2)	C22—H22A	0.9600
C7—C6	1.394 (2)	C22—H22B	0.9600
C8—H8	0.9300	C22—H22C	0.9600
C16—C17—C18	119.27 (18)	C9—C10—C11	120.23 (18)
C16—C17—H17	120.4	C9—C10—H10	119.9
C18—C17—H17	120.4	C11—C10—H10	119.9
N2—C2—C4	178.6 (2)	C9—C14—C13	119.32 (17)
N1—C1—C3	177.2 (2)	C9—C14—H14	120.3
C7—O1—C9	120.46 (13)	C13—C14—H14	120.3
C6—O2—C16	117.85 (12)	O3—C15—H15A	109.5
C12—O3—C15	118.08 (16)	O3—C15—H15B	109.5
C19—O4—C22	117.84 (16)	H15A—C15—H15B	109.5
C6—C5—C4	119.94 (15)	O3—C15—H15C	109.5
C6—C5—H5	120.0	H15A—C15—H15C	109.5
C4—C5—H5	120.0	H15B—C15—H15C	109.5
C8—C3—C4	119.71 (16)	C14—C13—C12	121.19 (19)
C8—C3—C1	121.20 (16)	C14—C13—H13	119.4
C4—C3—C1	119.08 (15)	C12—C13—H13	119.4
O1—C7—C8	124.19 (15)	C21—C16—C17	120.99 (16)
O1—C7—C6	115.44 (15)	C21—C16—O2	120.27 (16)
C8—C7—C6	120.27 (15)	C17—C16—O2	118.68 (17)
O2—C6—C5	124.12 (15)	O4—C19—C20	124.73 (18)
O2—C6—C7	115.91 (14)	O4—C19—C18	115.37 (17)
C5—C6—C7	119.96 (16)	C20—C19—C18	119.89 (17)
C5—C4—C3	120.11 (15)	C17—C18—C19	120.37 (17)
C5—C4—C2	118.90 (15)	C17—C18—H18	119.8
C3—C4—C2	120.98 (15)	C19—C18—H18	119.8
C7—C8—C3	119.99 (16)	C19—C20—C21	119.71 (18)
C7—C8—H8	120.0	C19—C20—H20	120.1
C3—C8—H8	120.0	C21—C20—H20	120.1
C10—C9—C14	120.23 (17)	C16—C21—C20	119.74 (17)
C10—C9—O1	116.98 (16)	C16—C21—H21	120.1
C14—C9—O1	122.49 (16)	C20—C21—H21	120.1
C12—C11—C10	119.92 (17)	O4—C22—H22A	109.5
C12—C11—H11	120.0	O4—C22—H22B	109.5
C10—C11—H11	120.0	H22A—C22—H22B	109.5
C11—C12—O3	124.51 (17)	O4—C22—H22C	109.5
C11—C12—C13	119.09 (18)	H22A—C22—H22C	109.5
O3—C12—C13	116.40 (18)	H22B—C22—H22C	109.5
C9—O1—C7—C8	33.4 (3)	C15—O3—C12—C11	−26.5 (3)
C9—O1—C7—C6	−150.32 (16)	C15—O3—C12—C13	154.53 (19)
C16—O2—C6—C5	−3.4 (2)	C14—C9—C10—C11	−0.7 (3)
C16—O2—C6—C7	177.01 (15)	O1—C9—C10—C11	−174.62 (16)
C4—C5—C6—O2	−178.51 (15)	C12—C11—C10—C9	−0.5 (3)
C4—C5—C6—C7	1.0 (3)	C10—C9—C14—C13	1.4 (3)
O1—C7—C6—O2	1.4 (2)	O1—C9—C14—C13	174.93 (18)
C8—C7—C6—O2	177.87 (15)	C9—C14—C13—C12	−0.9 (3)
O1—C7—C6—C5	−178.18 (15)	C11—C12—C13—C14	−0.4 (3)
C8—C7—C6—C5	−1.7 (3)	O3—C12—C13—C14	178.69 (18)
C6—C5—C4—C3	0.1 (2)	C18—C17—C16—C21	−0.7 (3)
C6—C5—C4—C2	178.85 (16)	C18—C17—C16—O2	176.69 (15)
C8—C3—C4—C5	−0.5 (2)	C6—O2—C16—C21	−83.9 (2)
C1—C3—C4—C5	178.88 (16)	C6—O2—C16—C17	98.69 (18)
C8—C3—C4—C2	−179.28 (16)	C22—O4—C19—C20	2.7 (3)
C1—C3—C4—C2	0.1 (2)	C22—O4—C19—C18	−177.31 (17)
O1—C7—C8—C3	177.40 (16)	C16—C17—C18—C19	−0.7 (3)
C6—C7—C8—C3	1.3 (3)	O4—C19—C18—C17	−178.31 (16)
C4—C3—C8—C7	−0.2 (3)	C20—C19—C18—C17	1.7 (3)
C1—C3—C8—C7	−179.53 (16)	O4—C19—C20—C21	178.76 (17)
C7—O1—C9—C10	−143.22 (17)	C18—C19—C20—C21	−1.2 (3)
C7—O1—C9—C14	43.1 (2)	C17—C16—C21—C20	1.1 (3)
C10—C11—C12—O3	−177.94 (17)	O2—C16—C21—C20	−176.20 (15)
C10—C11—C12—C13	1.1 (3)	C19—C20—C21—C16	−0.2 (3)