2,3-Dicyano-4-[(4-methyl­phenyl­sulfon­yl)­oxy]phenyl 4-methyl­benzene­sulfonate

Deng, Y.; Ma, C.; Zhang, X.

doi:10.1107/S1600536811009160

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o895

doi:10.1107/S1600536811009160

Open

access

2,3-Dicyano-4-[(4-methylphenylsulfonyl)oxy]phenyl 4-methylbenzenesulfonate

Yanhua Deng,^a Changqin Ma ^a ^* and Xiaomei Zhang ^a ^*

^aSchool of Chemistry and Chemical Technology, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: calm_tree@sohu.com, zhangxiaomei@sdu.edu.cn

(Received 28 February 2011; accepted 10 March 2011; online 15 March 2011)

In the title compound, C₂₂H₁₆N₂O₆S₂, the dihedral angle formed by the mean planes of the two benzene rings of the 4-methylphenylsulfonate 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_r = 468.49
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.098
S = 1.03
3848 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −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).

Supporting information

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

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

checkCIF report

Comment top

Dicyano compounds have been widely used to synthesize many useful materials such as phthalocyanines. Phthalocyanines are an interesting class of compounds, with increasingly diverse industrial and biomedical applications, for instance as liquid crystals, materials for optical storage (Kobayashi, 2001), oxidation catalysts, solar cell functional materials, gas sensors, nonlinear optical limiting devices (Shirk & Pong, 2000), photodynamic therapy agents (Lukyanets, 1999) and phthalocyanine dyes (Zhang et al. 2009).

The crystal structure of the title compound is shown in Fig. 1. The dihedral angle formed by the the mean planes of the two benzene rings of the 4-methylphenylsulfonate groups is 21.9 (1)° and each of these rings forms didhedral angles of 48.26 (9)° [C9-C14] and 52.73 (9)° [C16-C21] with the central benzene ring [C1-C6]. The bond distances (Allen et al. 1987) and angles are as expected and similar to those which are related in 4,5-biaminobenzene-1,2-dicarbonitrile (Zhang et al., 2009).

Related literature top

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 top

The title compound was prepared according to the method of Rey et al. (1998).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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).

Figures top

Fig. 1. A view of the title compound with displacement ellipsoids drawn at the 30% probability level.

2,3-Dicyano-4-[(4-methylphenylsulfonyl)oxy]phenyl 4-methylbenzenesulfonate top

Crystal data top

C₂₂H₁₆N₂O₆S₂	Z = 4
M_r = 468.49	F(000) = 968
Monoclinic, P2₁/c	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0498P)² + 0.6924P] where P = (F_o² + 2F_c²)/3
3848 reflections	(Δ/σ)_max = 0.018
291 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₂H₁₆N₂O₆S₂	V = 2183.5 (10) Å³
M_r = 468.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.2484 (16) Å	µ = 0.29 mm⁻¹
b = 21.478 (6) Å	T = 293 K
c = 16.331 (4) Å	0.42 × 0.31 × 0.26 mm
β = 94.940 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3848 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3237 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.929	R_int = 0.021
10754 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
3848 reflections	Δρ_min = −0.28 e Å⁻³
291 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₂O₆S₂
M_r	468.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.2484 (16), 21.478 (6), 16.331 (4)
β (°)	94.940 (4)
V (Å³)	2183.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.42 × 0.31 × 0.26

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.889, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	10754, 3848, 3237
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.098, 1.03
No. of reflections	3848
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Independent Innovation Foundation of Shandong University, IIFSDU.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kobayashi, N. (2001). Coord. Chem. Rev. 212, 99–103. CrossRef Google Scholar
Lukyanets, E. A. (1999). J. Porphyrins Phthalocyanines, 3, 424–426. CrossRef CAS Google Scholar
Rey, B., Keller, U. & Torres, T. (1998). J. Am. Chem. Soc. 120, 12808–12817. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shirk, J. S. & Pong, R. G. S. (2000). J. Phys. Chem. 104, 1438–1440. CrossRef CAS Google Scholar
Zhang, X., Wang, W., Jiang, J. & Ni, Z. (2009). Acta Cryst. E65, o837. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.