2,3-Dicyano-4-[(4-methyl-phenyl-sulfon-yl)-oxy]phenyl 4-methyl-benzene-sulfonate.

In the title compound, C(22)H(16)N(2)O(6)S(2), the dihedral angle formed by the mean planes of the two benzene rings of the 4-methyl-phenyl-sulfonate groups is 21.9 (1)° and these rings form dihedral angles of 48.26 (9) and 52.73 (9)° with the central benzene ring.

Related literature

For the applications of phthalocyanines, see: Kobayashi (2001 ▶); Shirk & Pong (2000 ▶); Lukyanets (1999 ▶). For the synthetic procedure, see: Rey et al. (1998 ▶). For a related structure, see: Zhang et al. (2009 ▶). For standard bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H16N2O6S2

M = 468.49

Monoclinic,

a = 6.2484 (16) Å

b = 21.478 (6) Å

c = 16.331 (4) Å

β = 94.940 (4)°

V = 2183.5 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.42 × 0.31 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.889, T max = 0.929

10754 measured reflections

3848 independent reflections

3237 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.098

S = 1.03

3848 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009160/lh5215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009160/lh5215Isup2.hkl

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

C22H16N2O6S2	Z = 4
Mr = 468.49	F(000) = 968
Monoclinic, P21/c	Dx = 1.425 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.2484 (16) Å	Cell parameters from 3848 reflections
b = 21.478 (6) Å	µ = 0.29 mm−1
c = 16.331 (4) Å	T = 293 K
β = 94.940 (4)°	Block, colorless
V = 2183.5 (10) Å3	0.42 × 0.31 × 0.26 mm

Bruker SMART CCD area-detector diffractometer	3848 independent reflections
Radiation source: fine-focus sealed tube	3237 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.889, Tmax = 0.929	k = −25→23
10754 measured reflections	l = −19→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.6924P] where P = (Fo2 + 2Fc2)/3
3848 reflections	(Δ/σ)max = 0.018
291 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.28 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
S1	1.13975 (8)	0.52784 (2)	0.81677 (3)	0.04334 (16)
S2	0.32466 (8)	0.28406 (2)	0.95047 (3)	0.04432 (16)
O1	1.3671 (2)	0.52925 (8)	0.82002 (10)	0.0664 (5)
O2	1.0278 (3)	0.55562 (7)	0.87978 (8)	0.0590 (4)
O3	1.0886 (2)	0.45361 (6)	0.81606 (8)	0.0403 (3)
O4	0.33997 (19)	0.35694 (6)	0.92363 (8)	0.0433 (3)
O5	0.4229 (2)	0.24810 (7)	0.89114 (9)	0.0565 (4)
O6	0.1032 (2)	0.27798 (8)	0.96165 (9)	0.0639 (5)
N1	0.2599 (3)	0.33703 (9)	0.70932 (11)	0.0598 (5)
N2	0.7716 (3)	0.41758 (10)	0.62978 (11)	0.0648 (6)
C1	0.5326 (3)	0.37925 (9)	0.89697 (11)	0.0364 (4)
C2	0.5550 (3)	0.38090 (8)	0.81323 (10)	0.0345 (4)
C3	0.7409 (3)	0.40812 (8)	0.78578 (10)	0.0346 (4)
C4	0.8981 (3)	0.43099 (8)	0.84335 (11)	0.0354 (4)
C5	0.8736 (3)	0.42786 (9)	0.92640 (11)	0.0411 (4)
H5	0.9816	0.4427	0.9642	0.049*
C6	0.6896 (3)	0.40281 (9)	0.95348 (11)	0.0419 (5)
H6	0.6709	0.4017	1.0093	0.050*
C7	0.3899 (3)	0.35619 (9)	0.75541 (11)	0.0405 (4)
C8	0.7631 (3)	0.41295 (9)	0.69862 (11)	0.0411 (4)
C9	1.0274 (3)	0.55195 (8)	0.72064 (11)	0.0380 (4)
C10	1.1458 (3)	0.54618 (10)	0.65330 (12)	0.0495 (5)
H10	1.2845	0.5301	0.6592	0.059*
C11	1.0549 (4)	0.56462 (11)	0.57751 (13)	0.0585 (6)
H11	1.1342	0.5611	0.5321	0.070*
C12	0.8488 (4)	0.58828 (10)	0.56718 (13)	0.0527 (5)
C13	0.7331 (4)	0.59329 (10)	0.63583 (13)	0.0520 (5)
H13	0.5942	0.6091	0.6298	0.062*
C14	0.8195 (3)	0.57529 (9)	0.71285 (12)	0.0440 (5)
H14	0.7405	0.5787	0.7584	0.053*
C15	0.7522 (5)	0.60828 (14)	0.48352 (15)	0.0837 (9)
H15A	0.8225	0.6454	0.4671	0.126*
H15B	0.6018	0.6164	0.4858	0.126*
H15C	0.7710	0.5758	0.4444	0.126*
C16	0.4794 (3)	0.28074 (9)	1.04487 (11)	0.0389 (4)
C17	0.6793 (3)	0.25268 (10)	1.04910 (13)	0.0481 (5)
H17	0.7307	0.2355	1.0023	0.058*
C18	0.8014 (3)	0.25053 (10)	1.12350 (13)	0.0512 (5)
H18	0.9358	0.2317	1.1266	0.061*
C19	0.7272 (3)	0.27601 (9)	1.19388 (12)	0.0446 (5)
C20	0.5257 (4)	0.30354 (10)	1.18779 (12)	0.0527 (5)
H20	0.4736	0.3206	1.2345	0.063*
C21	0.4005 (3)	0.30622 (10)	1.11400 (12)	0.0491 (5)
H21	0.2657	0.3248	1.1108	0.059*
C22	0.8603 (4)	0.27260 (12)	1.27527 (14)	0.0618 (6)
H22A	0.8330	0.3087	1.3075	0.093*
H22B	1.0099	0.2712	1.2660	0.093*
H22C	0.8227	0.2358	1.3041	0.093*

	U11	U22	U33	U12	U13	U23
S1	0.0492 (3)	0.0430 (3)	0.0363 (3)	−0.0115 (2)	−0.0055 (2)	0.0044 (2)
S2	0.0403 (3)	0.0553 (3)	0.0370 (3)	−0.0110 (2)	0.0015 (2)	0.0056 (2)
O1	0.0470 (9)	0.0735 (11)	0.0752 (11)	−0.0216 (8)	−0.0154 (8)	0.0208 (8)
O2	0.0942 (12)	0.0491 (9)	0.0331 (8)	−0.0083 (8)	0.0020 (7)	−0.0044 (6)
O3	0.0385 (7)	0.0393 (7)	0.0430 (7)	−0.0032 (5)	0.0033 (6)	0.0055 (6)
O4	0.0350 (7)	0.0556 (8)	0.0396 (7)	−0.0001 (6)	0.0038 (6)	0.0105 (6)
O5	0.0697 (10)	0.0563 (9)	0.0436 (8)	−0.0083 (7)	0.0052 (7)	−0.0055 (7)
O6	0.0414 (8)	0.0942 (13)	0.0556 (9)	−0.0221 (8)	0.0014 (7)	0.0152 (8)
N1	0.0575 (12)	0.0685 (13)	0.0504 (11)	−0.0097 (10)	−0.0119 (9)	−0.0008 (9)
N2	0.0778 (14)	0.0821 (14)	0.0347 (11)	−0.0164 (11)	0.0057 (9)	0.0001 (9)
C1	0.0366 (10)	0.0391 (10)	0.0331 (10)	−0.0001 (8)	0.0011 (8)	0.0066 (8)
C2	0.0362 (10)	0.0362 (10)	0.0302 (9)	0.0023 (8)	−0.0026 (7)	0.0026 (7)
C3	0.0413 (10)	0.0335 (9)	0.0287 (9)	0.0015 (8)	0.0011 (8)	0.0024 (7)
C4	0.0380 (10)	0.0341 (9)	0.0339 (10)	−0.0021 (8)	0.0015 (8)	0.0048 (7)
C5	0.0462 (11)	0.0443 (11)	0.0310 (10)	−0.0069 (9)	−0.0067 (8)	0.0038 (8)
C6	0.0493 (12)	0.0502 (11)	0.0258 (9)	−0.0044 (9)	0.0014 (8)	0.0047 (8)
C7	0.0409 (11)	0.0460 (11)	0.0339 (10)	−0.0020 (9)	−0.0007 (8)	0.0031 (8)
C8	0.0447 (11)	0.0455 (11)	0.0326 (11)	−0.0052 (9)	0.0008 (8)	−0.0005 (8)
C9	0.0446 (11)	0.0363 (10)	0.0330 (10)	−0.0047 (8)	0.0025 (8)	0.0025 (8)
C10	0.0468 (12)	0.0575 (13)	0.0453 (12)	0.0033 (10)	0.0101 (9)	0.0053 (10)
C11	0.0711 (16)	0.0677 (15)	0.0386 (12)	0.0055 (12)	0.0165 (11)	0.0062 (10)
C12	0.0712 (15)	0.0490 (12)	0.0367 (11)	0.0026 (11)	−0.0028 (10)	0.0027 (9)
C13	0.0516 (13)	0.0485 (12)	0.0546 (13)	0.0065 (10)	−0.0033 (10)	0.0034 (10)
C14	0.0475 (12)	0.0456 (11)	0.0398 (11)	0.0019 (9)	0.0089 (9)	0.0021 (9)
C15	0.115 (2)	0.088 (2)	0.0452 (14)	0.0199 (17)	−0.0107 (14)	0.0095 (13)
C16	0.0400 (10)	0.0415 (10)	0.0355 (10)	−0.0049 (8)	0.0047 (8)	0.0084 (8)
C17	0.0434 (11)	0.0595 (13)	0.0423 (11)	0.0019 (10)	0.0085 (9)	0.0015 (10)
C18	0.0387 (11)	0.0584 (13)	0.0558 (13)	0.0042 (9)	0.0005 (10)	0.0078 (10)
C19	0.0485 (12)	0.0408 (11)	0.0436 (11)	−0.0064 (9)	−0.0019 (9)	0.0091 (9)
C20	0.0623 (14)	0.0578 (13)	0.0381 (11)	0.0120 (11)	0.0041 (10)	−0.0009 (10)
C21	0.0454 (12)	0.0556 (13)	0.0465 (12)	0.0130 (10)	0.0044 (9)	0.0039 (10)
C22	0.0658 (15)	0.0642 (15)	0.0523 (13)	−0.0046 (12)	−0.0126 (11)	0.0068 (11)

S1—O1	1.4176 (16)	C10—H10	0.9300
S1—O2	1.4240 (16)	C11—C12	1.381 (3)
S1—O3	1.6259 (14)	C11—H11	0.9300
S1—C9	1.7422 (19)	C12—C13	1.389 (3)
S2—O6	1.4173 (15)	C12—C15	1.508 (3)
S2—O5	1.4193 (16)	C13—C14	1.381 (3)
S2—O4	1.6303 (15)	C13—H13	0.9300
S2—C16	1.7493 (19)	C14—H14	0.9300
O3—C4	1.394 (2)	C15—H15A	0.9600
O4—C1	1.399 (2)	C15—H15B	0.9600
N1—C7	1.136 (2)	C15—H15C	0.9600
N2—C8	1.135 (2)	C16—C21	1.383 (3)
C1—C6	1.383 (3)	C16—C17	1.383 (3)
C1—C2	1.387 (2)	C17—C18	1.379 (3)
C2—C3	1.408 (2)	C17—H17	0.9300
C2—C7	1.439 (3)	C18—C19	1.388 (3)
C3—C4	1.390 (2)	C18—H18	0.9300
C3—C8	1.446 (2)	C19—C20	1.387 (3)
C4—C5	1.380 (2)	C19—C22	1.508 (3)
C5—C6	1.377 (3)	C20—C21	1.380 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C9—C10	1.383 (3)	C22—H22A	0.9600
C9—C14	1.388 (3)	C22—H22B	0.9600
C10—C11	1.375 (3)	C22—H22C	0.9600
O1—S1—O2	121.13 (10)	C10—C11—H11	119.2
O1—S1—O3	102.52 (8)	C12—C11—H11	119.2
O2—S1—O3	107.91 (8)	C11—C12—C13	118.31 (19)
O1—S1—C9	110.63 (9)	C11—C12—C15	120.8 (2)
O2—S1—C9	109.99 (9)	C13—C12—C15	120.9 (2)
O3—S1—C9	102.78 (8)	C14—C13—C12	121.6 (2)
O6—S2—O5	121.48 (10)	C14—C13—H13	119.2
O6—S2—O4	101.75 (9)	C12—C13—H13	119.2
O5—S2—O4	107.47 (8)	C13—C14—C9	118.30 (18)
O6—S2—C16	110.75 (9)	C13—C14—H14	120.8
O5—S2—C16	109.93 (10)	C9—C14—H14	120.8
O4—S2—C16	103.61 (8)	C12—C15—H15A	109.5
C4—O3—S1	120.81 (11)	C12—C15—H15B	109.5
C1—O4—S2	118.97 (11)	H15A—C15—H15B	109.5
C6—C1—C2	121.50 (17)	C12—C15—H15C	109.5
C6—C1—O4	119.80 (16)	H15A—C15—H15C	109.5
C2—C1—O4	118.56 (16)	H15B—C15—H15C	109.5
C1—C2—C3	118.73 (16)	C21—C16—C17	121.02 (18)
C1—C2—C7	120.66 (17)	C21—C16—S2	119.64 (15)
C3—C2—C7	120.60 (16)	C17—C16—S2	119.34 (15)
C4—C3—C2	119.08 (16)	C18—C17—C16	119.17 (19)
C4—C3—C8	121.24 (16)	C18—C17—H17	120.4
C2—C3—C8	119.67 (16)	C16—C17—H17	120.4
C5—C4—C3	121.06 (17)	C17—C18—C19	121.17 (19)
C5—C4—O3	120.10 (16)	C17—C18—H18	119.4
C3—C4—O3	118.70 (15)	C19—C18—H18	119.4
C6—C5—C4	120.09 (17)	C20—C19—C18	118.32 (18)
C6—C5—H5	120.0	C20—C19—C22	120.83 (19)
C4—C5—H5	120.0	C18—C19—C22	120.83 (19)
C5—C6—C1	119.51 (17)	C21—C20—C19	121.53 (19)
C5—C6—H6	120.2	C21—C20—H20	119.2
C1—C6—H6	120.2	C19—C20—H20	119.2
N1—C7—C2	179.5 (2)	C20—C21—C16	118.78 (19)
N2—C8—C3	177.1 (2)	C20—C21—H21	120.6
C10—C9—C14	121.33 (18)	C16—C21—H21	120.6
C10—C9—S1	119.23 (15)	C19—C22—H22A	109.5
C14—C9—S1	119.42 (14)	C19—C22—H22B	109.5
C11—C10—C9	118.8 (2)	H22A—C22—H22B	109.5
C11—C10—H10	120.6	C19—C22—H22C	109.5
C9—C10—H10	120.6	H22A—C22—H22C	109.5
C10—C11—C12	121.6 (2)	H22B—C22—H22C	109.5
O1—S1—O3—C4	155.86 (13)	O2—S1—C9—C10	160.90 (16)
O2—S1—O3—C4	26.93 (15)	O3—S1—C9—C10	−84.39 (17)
C9—S1—O3—C4	−89.28 (14)	O1—S1—C9—C14	−156.90 (16)
O6—S2—O4—C1	−172.14 (13)	O2—S1—C9—C14	−20.45 (19)
O5—S2—O4—C1	−43.49 (15)	O3—S1—C9—C14	94.26 (16)
C16—S2—O4—C1	72.86 (14)	C14—C9—C10—C11	0.6 (3)
S2—O4—C1—C6	−88.93 (19)	S1—C9—C10—C11	179.22 (17)
S2—O4—C1—C2	95.31 (17)	C9—C10—C11—C12	−0.4 (3)
C6—C1—C2—C3	−1.0 (3)	C10—C11—C12—C13	0.1 (4)
O4—C1—C2—C3	174.72 (16)	C10—C11—C12—C15	179.9 (2)
C6—C1—C2—C7	−179.95 (18)	C11—C12—C13—C14	0.0 (3)
O4—C1—C2—C7	−4.3 (3)	C15—C12—C13—C14	−179.9 (2)
C1—C2—C3—C4	1.6 (3)	C12—C13—C14—C9	0.2 (3)
C7—C2—C3—C4	−179.39 (17)	C10—C9—C14—C13	−0.5 (3)
C1—C2—C3—C8	−177.15 (17)	S1—C9—C14—C13	−179.14 (15)
C7—C2—C3—C8	1.8 (3)	O6—S2—C16—C21	−35.2 (2)
C2—C3—C4—C5	−0.6 (3)	O5—S2—C16—C21	−172.16 (16)
C8—C3—C4—C5	178.17 (17)	O4—S2—C16—C21	73.23 (17)
C2—C3—C4—O3	175.24 (15)	O6—S2—C16—C17	144.94 (17)
C8—C3—C4—O3	−6.0 (3)	O5—S2—C16—C17	7.95 (19)
S1—O3—C4—C5	−76.16 (19)	O4—S2—C16—C17	−106.66 (16)
S1—O3—C4—C3	107.97 (17)	C21—C16—C17—C18	−0.3 (3)
C3—C4—C5—C6	−1.2 (3)	S2—C16—C17—C18	179.56 (16)
O3—C4—C5—C6	−176.94 (17)	C16—C17—C18—C19	0.0 (3)
C4—C5—C6—C1	1.8 (3)	C17—C18—C19—C20	0.4 (3)
C2—C1—C6—C5	−0.8 (3)	C17—C18—C19—C22	179.1 (2)
O4—C1—C6—C5	−176.40 (17)	C18—C19—C20—C21	−0.3 (3)
C1—C2—C7—N1	149 (100)	C22—C19—C20—C21	−179.0 (2)
C3—C2—C7—N1	−30 (31)	C19—C20—C21—C16	0.0 (3)
C4—C3—C8—N2	−134 (4)	C17—C16—C21—C20	0.4 (3)
C2—C3—C8—N2	44 (4)	S2—C16—C21—C20	−179.53 (16)
O1—S1—C9—C10	24.45 (19)