Dimethyl 3,3'-[(4,5-dicyano-1,2-phenyl-ene)bis-(-oxy)]dibenzoate.

In the title compound, C(24)H(16)N(2)O(6), the dihedral angles between the central 4,5-dicyano-1,2-phenyl-ene unit [maximum deviation from planarity = 0.014 (4) Å] and the pendant benzene rings are 73.62 (5) and 84.08 (6)°.

Related literature

For background to the properties and applications of phthalocyanines, see: Jiang & Ng (2009 ▶); Wang et al. (2011 ▶). For the synthesis, see Wang et al. (2009 ▶).

Experimental

Crystal data

C24H16N2O6

M = 428.39

Triclinic,

a = 10.1092 (11) Å

b = 10.3408 (11) Å

c = 10.8190 (14) Å

α = 82.284 (10)°

β = 85.991 (10)°

γ = 64.721 (11)°

V = 1013.3 (2) Å3

Z = 2

Cu Kα radiation

μ = 0.86 mm−1

T = 293 K

0.15 × 0.11 × 0.08 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.882, T max = 0.935

6668 measured reflections

3484 independent reflections

2790 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.119

S = 1.07

3484 reflections

292 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027432/hb6852sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027432/hb6852Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027432/hb6852Isup3.cml

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

C24H16N2O6	Z = 2
Mr = 428.39	F(000) = 444
Triclinic, P1	Dx = 1.404 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 10.1092 (11) Å	Cell parameters from 3269 reflections
b = 10.3408 (11) Å	θ = 2.1–64.7°
c = 10.8190 (14) Å	µ = 0.86 mm−1
α = 82.284 (10)°	T = 293 K
β = 85.991 (10)°	Block, colorless
γ = 64.721 (11)°	0.15 × 0.11 × 0.08 mm
V = 1013.3 (2) Å3

Agilent Xcalibur Eos Gemini diffractometer	3484 independent reflections
Radiation source: fine-focus sealed tube	2790 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 0 pixels mm-1	θmax = 66.0°, θmin = 4.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→12
Tmin = 0.882, Tmax = 0.935	l = −9→12
6668 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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.063P)2 + 0.0632P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.010
3484 reflections	Δρmax = 0.21 e Å−3
292 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (6)

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.36679 (12)	0.87260 (13)	0.45190 (11)	0.0500 (3)
O2	0.53609 (14)	0.59249 (13)	0.39290 (10)	0.0547 (3)
O3	0.2830 (2)	0.7221 (2)	−0.11360 (13)	0.0933 (6)
O4	0.26548 (15)	0.56809 (16)	0.04354 (12)	0.0648 (4)
O5	−0.01163 (14)	0.88074 (16)	0.18060 (12)	0.0635 (4)
O6	−0.19904 (13)	0.89259 (17)	0.30884 (15)	0.0738 (4)
N1	1.0057 (2)	0.4624 (2)	0.7376 (2)	0.0809 (6)
N2	0.7608 (2)	0.8509 (2)	0.83423 (15)	0.0723 (5)
C1	0.75592 (17)	0.61523 (18)	0.63383 (14)	0.0447 (4)
C2	0.66927 (17)	0.75363 (18)	0.66704 (13)	0.0430 (4)
C3	0.53669 (17)	0.83798 (18)	0.60837 (14)	0.0450 (4)
H3	0.4778	0.9289	0.6315	0.054*
C4	0.49313 (17)	0.78577 (18)	0.51556 (14)	0.0432 (4)
C5	0.57990 (18)	0.64856 (18)	0.48157 (14)	0.0449 (4)
C6	0.71024 (19)	0.56367 (18)	0.54090 (15)	0.0479 (4)
H6	0.7675	0.4720	0.5187	0.058*
C7	0.51505 (17)	0.66227 (18)	0.27123 (14)	0.0449 (4)
C8	0.57881 (19)	0.7533 (2)	0.22567 (16)	0.0514 (4)
H8	0.6374	0.7728	0.2761	0.062*
C9	0.5536 (2)	0.8156 (2)	0.10261 (17)	0.0586 (5)
H9	0.5948	0.8783	0.0706	0.070*
C10	0.4682 (2)	0.7854 (2)	0.02736 (16)	0.0568 (5)
H10	0.4523	0.8275	−0.0550	0.068*
C11	0.40625 (18)	0.69222 (19)	0.07461 (15)	0.0482 (4)
C12	0.43022 (18)	0.62997 (18)	0.19734 (15)	0.0469 (4)
H12	0.3894	0.5669	0.2296	0.056*
C13	0.24755 (16)	0.83783 (17)	0.47464 (14)	0.0416 (4)
C14	0.21672 (18)	0.78724 (18)	0.59275 (15)	0.0491 (4)
H14	0.2801	0.7667	0.6583	0.059*
C15	0.0898 (2)	0.7680 (2)	0.61111 (17)	0.0587 (5)
H15	0.0671	0.7339	0.6899	0.070*
C16	−0.00390 (19)	0.7989 (2)	0.51367 (18)	0.0575 (5)
H16	−0.0905	0.7879	0.5277	0.069*
C17	0.02986 (17)	0.84627 (18)	0.39509 (16)	0.0469 (4)
C18	0.15724 (17)	0.86604 (17)	0.37489 (15)	0.0429 (4)
H18	0.1815	0.8977	0.2957	0.051*
C19	0.71881 (18)	0.8084 (2)	0.76095 (15)	0.0500 (4)
C20	0.8951 (2)	0.5287 (2)	0.69212 (18)	0.0556 (4)
C21	−0.07390 (18)	0.87628 (19)	0.29280 (18)	0.0537 (4)
C22	0.3129 (2)	0.6638 (2)	−0.00915 (16)	0.0563 (5)
C23	0.1746 (2)	0.5351 (3)	−0.0331 (2)	0.0756 (6)
H23A	0.0814	0.6165	−0.0446	0.113*
H23B	0.1605	0.4533	0.0073	0.113*
H23C	0.2215	0.5137	−0.1128	0.113*
C24	−0.1000 (3)	0.8966 (3)	0.0748 (2)	0.0795 (7)
H24A	−0.1324	0.8210	0.0842	0.119*
H24B	−0.0428	0.8913	−0.0006	0.119*
H24C	−0.1834	0.9882	0.0706	0.119*

	U11	U22	U33	U12	U13	U23
O1	0.0467 (6)	0.0577 (7)	0.0502 (6)	−0.0286 (6)	−0.0169 (5)	0.0096 (5)
O2	0.0801 (9)	0.0585 (7)	0.0403 (6)	−0.0430 (7)	−0.0184 (5)	0.0024 (5)
O3	0.1357 (15)	0.1149 (14)	0.0484 (8)	−0.0717 (12)	−0.0370 (9)	0.0116 (8)
O4	0.0720 (9)	0.0846 (10)	0.0503 (7)	−0.0426 (8)	−0.0150 (6)	−0.0085 (7)
O5	0.0553 (7)	0.0812 (9)	0.0595 (8)	−0.0331 (7)	−0.0194 (6)	−0.0020 (6)
O6	0.0421 (7)	0.0856 (10)	0.0996 (11)	−0.0272 (7)	−0.0076 (7)	−0.0257 (8)
N1	0.0627 (11)	0.0727 (12)	0.1003 (14)	−0.0196 (9)	−0.0356 (10)	0.0000 (10)
N2	0.0790 (12)	0.0964 (14)	0.0541 (9)	−0.0447 (11)	−0.0119 (8)	−0.0180 (9)
C1	0.0451 (9)	0.0530 (9)	0.0404 (8)	−0.0258 (8)	−0.0071 (6)	0.0011 (7)
C2	0.0454 (8)	0.0566 (9)	0.0331 (7)	−0.0273 (7)	−0.0041 (6)	−0.0034 (6)
C3	0.0462 (9)	0.0517 (9)	0.0400 (8)	−0.0233 (7)	−0.0017 (6)	−0.0052 (7)
C4	0.0443 (8)	0.0520 (9)	0.0374 (7)	−0.0257 (7)	−0.0096 (6)	0.0040 (6)
C5	0.0548 (9)	0.0540 (9)	0.0363 (8)	−0.0332 (8)	−0.0091 (7)	0.0003 (7)
C6	0.0546 (10)	0.0472 (9)	0.0444 (9)	−0.0230 (8)	−0.0073 (7)	−0.0047 (7)
C7	0.0479 (9)	0.0506 (9)	0.0374 (8)	−0.0214 (7)	−0.0064 (6)	−0.0035 (7)
C8	0.0511 (9)	0.0613 (10)	0.0504 (9)	−0.0318 (8)	−0.0033 (7)	−0.0063 (8)
C9	0.0630 (11)	0.0674 (12)	0.0525 (10)	−0.0370 (10)	0.0042 (8)	−0.0002 (8)
C10	0.0604 (11)	0.0681 (12)	0.0402 (9)	−0.0276 (9)	−0.0014 (7)	0.0012 (8)
C11	0.0484 (9)	0.0570 (10)	0.0386 (8)	−0.0209 (8)	−0.0031 (7)	−0.0067 (7)
C12	0.0512 (9)	0.0541 (9)	0.0403 (8)	−0.0265 (8)	−0.0048 (7)	−0.0050 (7)
C13	0.0391 (8)	0.0427 (8)	0.0440 (8)	−0.0178 (7)	−0.0048 (6)	−0.0047 (6)
C14	0.0530 (9)	0.0520 (10)	0.0395 (8)	−0.0195 (8)	−0.0034 (7)	−0.0040 (7)
C15	0.0596 (11)	0.0651 (11)	0.0501 (10)	−0.0279 (9)	0.0105 (8)	−0.0031 (8)
C16	0.0458 (9)	0.0620 (11)	0.0661 (11)	−0.0254 (9)	0.0077 (8)	−0.0076 (9)
C17	0.0407 (8)	0.0447 (9)	0.0557 (10)	−0.0169 (7)	−0.0034 (7)	−0.0094 (7)
C18	0.0418 (8)	0.0459 (8)	0.0423 (8)	−0.0199 (7)	−0.0046 (6)	−0.0030 (6)
C19	0.0508 (9)	0.0649 (11)	0.0396 (8)	−0.0286 (9)	−0.0041 (7)	−0.0064 (7)
C20	0.0548 (11)	0.0584 (11)	0.0580 (10)	−0.0272 (9)	−0.0146 (8)	−0.0024 (8)
C21	0.0429 (9)	0.0481 (9)	0.0723 (12)	−0.0185 (8)	−0.0101 (8)	−0.0124 (8)
C22	0.0604 (11)	0.0652 (11)	0.0419 (9)	−0.0232 (9)	−0.0091 (8)	−0.0087 (8)
C23	0.0767 (14)	0.0902 (16)	0.0725 (13)	−0.0414 (13)	−0.0213 (11)	−0.0192 (12)
C24	0.0740 (14)	0.0946 (17)	0.0736 (14)	−0.0367 (13)	−0.0357 (11)	−0.0003 (12)

O1—C4	1.3746 (19)	C8—H8	0.9300
O1—C13	1.3956 (19)	C9—C10	1.379 (3)
O2—C5	1.3714 (19)	C9—H9	0.9300
O2—C7	1.3970 (19)	C10—C11	1.386 (3)
O3—C22	1.200 (2)	C10—H10	0.9300
O4—C22	1.323 (2)	C11—C12	1.385 (2)
O4—C23	1.449 (2)	C11—C22	1.491 (2)
O5—C21	1.332 (2)	C12—H12	0.9300
O5—C24	1.450 (2)	C13—C14	1.381 (2)
O6—C21	1.206 (2)	C13—C18	1.382 (2)
N1—C20	1.138 (2)	C14—C15	1.378 (3)
N2—C19	1.141 (2)	C14—H14	0.9300
C1—C6	1.388 (2)	C15—C16	1.379 (3)
C1—C2	1.403 (2)	C15—H15	0.9300
C1—C20	1.440 (2)	C16—C17	1.384 (3)
C2—C3	1.390 (2)	C16—H16	0.9300
C2—C19	1.440 (2)	C17—C18	1.386 (2)
C3—C4	1.380 (2)	C17—C21	1.488 (2)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.396 (2)	C23—H23A	0.9600
C5—C6	1.378 (2)	C23—H23B	0.9600
C6—H6	0.9300	C23—H23C	0.9600
C7—C8	1.376 (2)	C24—H24A	0.9600
C7—C12	1.378 (2)	C24—H24B	0.9600
C8—C9	1.389 (3)	C24—H24C	0.9600
C4—O1—C13	117.31 (12)	C11—C12—H12	120.3
C5—O2—C7	118.67 (13)	C14—C13—C18	122.10 (15)
C22—O4—C23	115.98 (16)	C14—C13—O1	121.36 (14)
C21—O5—C24	116.20 (16)	C18—C13—O1	116.39 (13)
C6—C1—C2	119.92 (15)	C15—C14—C13	118.36 (16)
C6—C1—C20	119.81 (16)	C15—C14—H14	120.8
C2—C1—C20	120.21 (15)	C13—C14—H14	120.8
C3—C2—C1	119.98 (14)	C14—C15—C16	120.56 (16)
C3—C2—C19	120.20 (15)	C14—C15—H15	119.7
C1—C2—C19	119.82 (15)	C16—C15—H15	119.7
C4—C3—C2	119.47 (16)	C15—C16—C17	120.55 (17)
C4—C3—H3	120.3	C15—C16—H16	119.7
C2—C3—H3	120.3	C17—C16—H16	119.7
O1—C4—C3	119.52 (15)	C16—C17—C18	119.65 (16)
O1—C4—C5	119.78 (14)	C16—C17—C21	118.46 (16)
C3—C4—C5	120.62 (15)	C18—C17—C21	121.89 (16)
O2—C5—C6	118.30 (15)	C13—C18—C17	118.74 (15)
O2—C5—C4	121.55 (15)	C13—C18—H18	120.6
C6—C5—C4	120.09 (15)	C17—C18—H18	120.6
C5—C6—C1	119.90 (16)	N2—C19—C2	178.62 (18)
C5—C6—H6	120.0	N1—C20—C1	178.7 (2)
C1—C6—H6	120.0	O6—C21—O5	123.65 (17)
C8—C7—C12	121.66 (15)	O6—C21—C17	124.32 (18)
C8—C7—O2	122.68 (14)	O5—C21—C17	112.02 (14)
C12—C7—O2	115.61 (15)	O3—C22—O4	123.13 (18)
C7—C8—C9	118.44 (16)	O3—C22—C11	123.71 (19)
C7—C8—H8	120.8	O4—C22—C11	113.16 (15)
C9—C8—H8	120.8	O4—C23—H23A	109.5
C10—C9—C8	120.78 (18)	O4—C23—H23B	109.5
C10—C9—H9	119.6	H23A—C23—H23B	109.5
C8—C9—H9	119.6	O4—C23—H23C	109.5
C9—C10—C11	119.90 (16)	H23A—C23—H23C	109.5
C9—C10—H10	120.0	H23B—C23—H23C	109.5
C11—C10—H10	120.0	O5—C24—H24A	109.5
C12—C11—C10	119.81 (16)	O5—C24—H24B	109.5
C12—C11—C22	121.87 (16)	H24A—C24—H24B	109.5
C10—C11—C22	118.31 (16)	O5—C24—H24C	109.5
C7—C12—C11	119.39 (16)	H24A—C24—H24C	109.5
C7—C12—H12	120.3	H24B—C24—H24C	109.5