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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2229
https://doi.org/10.1107/S160053681003062X

1,2-Bis{2-[(1,3-benzo­thia­zol-2-yl)sulfanylmeth­yl]phen­­oxy}ethane

Liang-Wei Zhang,a Wen-Yu Wu,a Zhong-Xing Su,a Ai-Jiang Zhanga and Xiang Liua*

aState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China
*Correspondence e-mail: liuxiang@lzu.edu.cn

(Received 24 July 2010; accepted 31 July 2010; online 11 August 2010)

The mol­ecule of the title compound, C30H24N2O2S4, adopts a Z-shaped conformation. The terminal benzothia­zole ring systems are oriented at a dihedral angle of 60.81 (8)°, while the central benzene rings are twisted to each other by a dihedral angle of 13.56 (14)°. Weak inter­molecular C—H⋯π inter­actions are present in the crystal structure.

Related literature

For the biological activity of benzothia­zoles and their deriva­tives, see: Paramashivappa et al. (2002[Paramashivappa, R., Kumar, P. P., Rao, P. V. S. & Rao, A. S. (2002). Bioorg. Med. Chem. Lett. 13, 657-660.]); Kočí et al. (2002[Kočí, J., Klimešová, V., Waisser, K., Kaustová, J., Dahse, H. M. & Möllmann, U. (2002). Bioorg. Med. Chem. Lett. 12, 3275-3278.]); Fei et al. (2009[Fei, X.-N., Gu, Y.-C., Ban, Y., Liu, Z.-J. & Zhang, B.-L. (2009). Bioorg. Med. Chem. 17, 585-591.]). For the preparation of the title compound, see: Yuan et al. (2005[Yuan, D.-R., Yan, J.-M., Yu, C.-Z. & Xie, R.-H. (2005). Chin. Chem. Lett. 16, 147-150.]); Siva & Murugan (2005[Siva, A. & Murugan, E. (2005). J. Mol. Catal. A Chem. 241, 101-110.]); Gruter et al. (1994[Gruter, G. J. M., Akkerman, O. S. & Bickelhaupt, F. (1994). J. Org. Chem. 59, 4473-4481.]); Kumar et al. (2005[Kumar, R. V., Kumar, V. S. R. S. & Gopal, K. R. (2005). J. Heterocycl. Chem. 42, 153-156.]).

[Scheme 1]

Experimental

Crystal data

  • C30H24N2O2S4

  • Mr = 572.75

  • Triclinic, [P \overline 1]

  • a = 9.8194 (6) Å

  • b = 10.7740 (8) Å

  • c = 14.0716 (9) Å

  • α = 82.422 (1)°

  • β = 76.285 (1)°

  • γ = 68.993 (1)°

  • V = 1348.32 (16) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.39 mm−1

  • T = 296 K

  • 0.35 × 0.32 × 0.30 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.877, Tmax = 0.893

  • 7093 measured reflections

  • 4947 independent reflections

  • 3531 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.101

  • S = 1.01

  • 4947 reflections

  • 343 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3,and Cg5 are centroids of the S4,C24,N2,C25,C30, C1–C6 and C17–C22 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3⋯Cg2i 0.93 2.91 3.727 (3) 147
C13—H13⋯Cg3ii 0.93 2.87 3.705 (3) 149
C18—H18⋯Cg3 0.93 2.81 3.636 (3) 149
C21—H21⋯Cg2iii 0.93 2.78 3.457 (3) 131
C29—H29⋯Cg5ii 0.93 2.79 3.559 (3) 141
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681003062X/xu5002sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003062X/xu5002Isup2.hkl

checkCIF report


Comment top

It is reported that benzothiazoles and their derivatives have showed a wide variety of biological activities, such as anti-inflammatory, antimycobacteriva, and capability of labeling cancer cells (Paramashivappa et al., 2002; Kočí et al., 2002; Fei et al., 2009). As an important class of benzothiazoles, benzothiazole-2-thiol also exhibits potential biological activities. Therefore, the title compound was synthesized.

In the title compound (Fig. 1), the dihedral angles between each benzene ring and benzothiazole ring pair where the two rings are linked to each other are 87.00and 60.18°, respectively, while the dihedral angle between the two benzene rings is 13.63°. The stability of the structure is ascribed to the weak C—H···π interactions. In the crystal (Fig. 2), the molecules are linked by weak C—H···π interactions and intermolecular S···S interactions.

Related literature top

For the biological activity of benzothiazoles and their derivatives, see: Paramashivappa et al. (2002); Kočí et al. (2002); Fei et al. (2009). For the preparation of the title compound, see: Yuan et al. (2005); Siva & Murugan (2005); Gruter et al. (1994); Kumar et al. (2005).

Experimental top

All reagents and solvents were obtained from commercial sources and needed to be further purified. 1,2-bis(o-tolyloxy)ethane was synthesized according to the method proposed by Yuan et al. (2005). 1,2-Bis(2-(bromomethyl)phenoxy)ethane was prepared following previously reported methods, but with some modification (Siva & Murugan, 2005; Gruter et al., 1994). 1,2-Bis-(o-tolyloxy)ethane (10 mmol), N-bromosuccinamide (30 mmol), benzoyl peroxide (20 mmol) and CCl4 (50 ml) were taken in a 100 ml round-bottom flask. The reaction mixture was refluxed for 6 h under an IR lamp (250 W) irradiation. Subsequently, the solid formed in the reaction was removed by fltration. The solvent was evaporated under vacuum to give the crude product, which was thereafter recrystallized (ethanol-acetone) to prodcue pale-yellow needles, yield: 76%. The title compound was synthesized according to the related literature (Kumar et al., 2005). A mixture of 2-mercaptobenzothiazole (4 mmol), 1,2-bis(2-(bromomethyl)p-henoxy)ethane (2 mmol) and finely grounded anhydrous K2CO3 (4 mmol) in acetone was refluxed for 2 h (TLC monitoring). The reaction mixture was then cooled to room temperature and filtered. Evaporation of the filtrate yielded the crude products. Finally, the crude products were purified by recrystallization from the hexane-ethyl acetate solution, yield: 84%.

Refinement top

H atoms were placed in calculated positions and were refined in a riding-model approximation with C—H = 0.93 or 0.97 Å and with Uiso(H) = 1.2Ueq(C).

Structure description top

It is reported that benzothiazoles and their derivatives have showed a wide variety of biological activities, such as anti-inflammatory, antimycobacteriva, and capability of labeling cancer cells (Paramashivappa et al., 2002; Kočí et al., 2002; Fei et al., 2009). As an important class of benzothiazoles, benzothiazole-2-thiol also exhibits potential biological activities. Therefore, the title compound was synthesized.

In the title compound (Fig. 1), the dihedral angles between each benzene ring and benzothiazole ring pair where the two rings are linked to each other are 87.00and 60.18°, respectively, while the dihedral angle between the two benzene rings is 13.63°. The stability of the structure is ascribed to the weak C—H···π interactions. In the crystal (Fig. 2), the molecules are linked by weak C—H···π interactions and intermolecular S···S interactions.

For the biological activity of benzothiazoles and their derivatives, see: Paramashivappa et al. (2002); Kočí et al. (2002); Fei et al. (2009). For the preparation of the title compound, see: Yuan et al. (2005); Siva & Murugan (2005); Gruter et al. (1994); Kumar et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with the weak intermolecular S···S and C—H···π interactions.
1,2-Bis{2-[(1,3-benzothiazol-2-yl)sulfanylmethyl]phenoxy}ethane top
Crystal data top
C30H24N2O2S4Z = 2
Mr = 572.75F(000) = 596
Triclinic, P1Dx = 1.411 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8194 (6) ÅCell parameters from 1819 reflections
b = 10.7740 (8) Åθ = 2.3–22.8°
c = 14.0716 (9) ŵ = 0.39 mm−1
α = 82.422 (1)°T = 296 K
β = 76.285 (1)°Block, yellow
γ = 68.993 (1)°0.35 × 0.32 × 0.30 mm
V = 1348.32 (16) Å3
Data collection top
Bruker APEXII CCD
diffractometer		4947 independent reflections
Radiation source: fine-focus sealed tube3531 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −11→10
Tmin = 0.877, Tmax = 0.893k = −11→13
7093 measured reflectionsl = −17→10
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0313P)2 + 0.6717P]
where P = (Fo2 + 2Fc2)/3
4947 reflections(Δ/σ)max < 0.001
343 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C30H24N2O2S4γ = 68.993 (1)°
Mr = 572.75V = 1348.32 (16) Å3
Triclinic, P1Z = 2
a = 9.8194 (6) ÅMo Kα radiation
b = 10.7740 (8) ŵ = 0.39 mm−1
c = 14.0716 (9) ÅT = 296 K
α = 82.422 (1)°0.35 × 0.32 × 0.30 mm
β = 76.285 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		4947 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3531 reflections with I > 2σ(I)
Tmin = 0.877, Tmax = 0.893Rint = 0.022
7093 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.01Δρmax = 0.24 e Å−3
4947 reflectionsΔρmin = −0.28 e Å−3
343 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
xyzUiso*/Ueq
S10.25411 (9)0.18208 (8)0.27373 (6)0.0552 (2)
S20.38885 (9)0.13160 (8)0.44913 (6)0.0523 (2)
S30.47855 (8)0.88320 (7)0.11847 (5)0.0451 (2)
S40.80655 (8)0.86358 (8)0.05966 (5)0.0463 (2)
N10.1731 (2)0.3580 (2)0.40420 (16)0.0432 (6)
N20.6259 (2)0.9606 (2)0.22042 (15)0.0402 (5)
O10.5007 (2)0.38268 (19)0.38482 (13)0.0479 (5)
O20.4699 (2)0.58394 (19)0.16478 (13)0.0474 (5)
C10.0873 (3)0.4137 (3)0.33328 (18)0.0387 (6)
C2−0.0182 (3)0.5403 (3)0.3337 (2)0.0503 (7)
H2−0.03540.59680.38310.060*
C3−0.0972 (3)0.5814 (3)0.2596 (2)0.0531 (8)
H3−0.16790.66640.25910.064*
C4−0.0727 (3)0.4980 (3)0.1859 (2)0.0536 (8)
H4−0.12820.52740.13720.064*
C50.0320 (3)0.3725 (3)0.1834 (2)0.0512 (8)
H50.04850.31680.13360.061*
C60.1124 (3)0.3313 (3)0.2573 (2)0.0413 (6)
C70.2632 (3)0.2401 (3)0.38187 (19)0.0407 (6)
C80.3907 (3)0.2396 (3)0.53801 (19)0.0484 (7)
H8A0.31800.32720.52990.058*
H8B0.36120.20410.60360.058*
C90.5399 (3)0.2527 (3)0.52779 (18)0.0396 (6)
C100.6279 (3)0.1936 (3)0.5960 (2)0.0530 (8)
H100.59510.14190.64840.064*
C110.7635 (4)0.2098 (4)0.5880 (2)0.0670 (10)
H110.82140.16880.63440.080*
C120.8124 (4)0.2859 (4)0.5117 (2)0.0664 (9)
H120.90340.29730.50680.080*
C130.7282 (3)0.3463 (3)0.4420 (2)0.0520 (8)
H130.76230.39780.39000.062*
C140.5929 (3)0.3296 (3)0.44972 (19)0.0399 (6)
C150.5447 (3)0.4641 (3)0.30440 (19)0.0445 (7)
H15A0.64180.41610.26640.053*
H15B0.54900.54370.32700.053*
C160.4271 (3)0.4995 (3)0.24431 (18)0.0432 (7)
H16A0.42440.42020.22040.052*
H16B0.32970.54580.28270.052*
C170.3904 (3)0.6233 (2)0.09199 (18)0.0364 (6)
C180.2737 (3)0.5827 (3)0.0873 (2)0.0430 (7)
H180.24230.52670.13670.052*
C190.2042 (3)0.6262 (3)0.0083 (2)0.0453 (7)
H190.12550.59930.00510.054*
C200.2497 (3)0.7087 (3)−0.0653 (2)0.0459 (7)
H200.20300.7366−0.11850.055*
C210.3653 (3)0.7495 (3)−0.05950 (18)0.0411 (7)
H210.39580.8056−0.10930.049*
C220.4369 (3)0.7090 (2)0.01829 (18)0.0353 (6)
C230.5585 (3)0.7579 (3)0.02708 (18)0.0398 (6)
H23A0.59610.7963−0.03540.048*
H23B0.64030.68480.04720.048*
C240.6343 (3)0.9053 (3)0.14192 (18)0.0363 (6)
C250.7615 (3)0.9749 (3)0.21972 (18)0.0371 (6)
C260.7899 (3)1.0335 (3)0.2921 (2)0.0515 (8)
H260.71571.06650.34650.062*
C270.9282 (3)1.0417 (3)0.2820 (2)0.0547 (8)
H270.94811.08070.32990.066*
C281.0395 (3)0.9924 (3)0.2009 (2)0.0513 (8)
H281.13280.99940.19540.062*
C291.0153 (3)0.9342 (3)0.1293 (2)0.0474 (7)
H291.09080.90050.07570.057*
C300.8741 (3)0.9266 (3)0.13876 (18)0.0374 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0584 (5)0.0437 (4)0.0664 (5)−0.0079 (4)−0.0286 (4)−0.0108 (4)
S20.0542 (5)0.0422 (4)0.0638 (5)−0.0135 (4)−0.0279 (4)0.0061 (4)
S30.0378 (4)0.0500 (4)0.0513 (4)−0.0185 (3)−0.0077 (3)−0.0086 (3)
S40.0419 (4)0.0579 (5)0.0430 (4)−0.0221 (4)−0.0020 (3)−0.0130 (3)
N10.0376 (13)0.0486 (15)0.0428 (13)−0.0121 (11)−0.0114 (11)−0.0018 (11)
N20.0387 (13)0.0478 (14)0.0362 (13)−0.0192 (11)−0.0053 (10)−0.0009 (10)
O10.0507 (12)0.0590 (13)0.0407 (11)−0.0260 (10)−0.0219 (9)0.0186 (9)
O20.0552 (12)0.0556 (12)0.0443 (11)−0.0319 (10)−0.0253 (10)0.0184 (9)
C10.0325 (14)0.0469 (17)0.0384 (15)−0.0156 (13)−0.0097 (12)0.0025 (13)
C20.0449 (17)0.0493 (18)0.0533 (18)−0.0079 (14)−0.0136 (14)−0.0082 (14)
C30.0460 (18)0.0505 (19)0.058 (2)−0.0080 (15)−0.0185 (15)0.0025 (15)
C40.0505 (19)0.059 (2)0.0560 (19)−0.0182 (16)−0.0266 (15)0.0095 (16)
C50.0550 (19)0.056 (2)0.0511 (18)−0.0213 (16)−0.0223 (15)−0.0051 (15)
C60.0382 (16)0.0431 (16)0.0465 (16)−0.0160 (13)−0.0135 (13)−0.0004 (13)
C70.0375 (16)0.0430 (17)0.0457 (16)−0.0182 (13)−0.0125 (13)0.0039 (13)
C80.0484 (18)0.0574 (19)0.0344 (15)−0.0146 (15)−0.0087 (13)0.0060 (13)
C90.0444 (16)0.0392 (16)0.0332 (14)−0.0095 (13)−0.0117 (12)−0.0010 (12)
C100.063 (2)0.0532 (19)0.0415 (17)−0.0156 (16)−0.0222 (15)0.0095 (14)
C110.069 (2)0.076 (2)0.065 (2)−0.022 (2)−0.0438 (19)0.0129 (19)
C120.059 (2)0.085 (3)0.069 (2)−0.0321 (19)−0.0317 (18)0.006 (2)
C130.0577 (19)0.060 (2)0.0500 (18)−0.0305 (16)−0.0222 (15)0.0093 (15)
C140.0438 (16)0.0391 (16)0.0381 (15)−0.0115 (13)−0.0159 (13)0.0000 (12)
C150.0535 (18)0.0451 (17)0.0400 (16)−0.0223 (14)−0.0165 (13)0.0092 (13)
C160.0516 (17)0.0456 (17)0.0371 (15)−0.0234 (14)−0.0147 (13)0.0117 (12)
C170.0430 (16)0.0354 (15)0.0341 (14)−0.0144 (12)−0.0152 (12)0.0037 (11)
C180.0489 (17)0.0422 (17)0.0442 (16)−0.0230 (14)−0.0141 (13)0.0062 (13)
C190.0438 (17)0.0482 (17)0.0527 (18)−0.0187 (14)−0.0195 (14)−0.0060 (14)
C200.0550 (18)0.0471 (17)0.0395 (16)−0.0140 (15)−0.0224 (14)−0.0020 (13)
C210.0477 (17)0.0403 (16)0.0320 (14)−0.0105 (13)−0.0106 (12)0.0016 (12)
C220.0366 (15)0.0330 (14)0.0352 (14)−0.0103 (12)−0.0081 (11)−0.0017 (11)
C230.0407 (16)0.0417 (16)0.0389 (15)−0.0186 (13)−0.0063 (12)0.0009 (12)
C240.0362 (15)0.0344 (15)0.0382 (15)−0.0143 (12)−0.0076 (12)0.0051 (12)
C250.0364 (15)0.0387 (15)0.0361 (15)−0.0145 (12)−0.0080 (12)0.0039 (12)
C260.0506 (19)0.063 (2)0.0437 (17)−0.0228 (16)−0.0056 (14)−0.0106 (15)
C270.055 (2)0.065 (2)0.0519 (19)−0.0229 (17)−0.0191 (16)−0.0102 (16)
C280.0379 (17)0.059 (2)0.063 (2)−0.0198 (15)−0.0142 (15)−0.0084 (16)
C290.0374 (16)0.0505 (18)0.0521 (18)−0.0150 (14)−0.0030 (13)−0.0061 (14)
C300.0369 (15)0.0370 (15)0.0389 (15)−0.0140 (12)−0.0082 (12)0.0002 (12)
Geometric parameters (Å, º) top
S1—C61.739 (3)C11—H110.9300
S1—C71.752 (3)C12—C131.379 (4)
S2—C71.736 (3)C12—H120.9300
S2—C81.824 (3)C13—C141.381 (4)
S3—C241.740 (3)C13—H130.9300
S3—C231.820 (3)C15—C161.501 (3)
S4—C301.736 (3)C15—H15A0.9700
S4—C241.751 (3)C15—H15B0.9700
N1—C71.290 (3)C16—H16A0.9700
N1—C11.394 (3)C16—H16B0.9700
N2—C241.295 (3)C17—C181.383 (3)
N2—C251.393 (3)C17—C221.400 (3)
O1—C141.365 (3)C18—C191.383 (4)
O1—C151.419 (3)C18—H180.9300
O2—C171.366 (3)C19—C201.372 (4)
O2—C161.428 (3)C19—H190.9300
C1—C21.386 (4)C20—C211.379 (4)
C1—C61.400 (4)C20—H200.9300
C2—C31.378 (4)C21—C221.379 (3)
C2—H20.9300C21—H210.9300
C3—C41.383 (4)C22—C231.502 (3)
C3—H30.9300C23—H23A0.9700
C4—C51.373 (4)C23—H23B0.9700
C4—H40.9300C25—C301.392 (3)
C5—C61.385 (4)C25—C261.394 (4)
C5—H50.9300C26—C271.365 (4)
C8—C91.494 (4)C26—H260.9300
C8—H8A0.9700C27—C281.390 (4)
C8—H8B0.9700C27—H270.9300
C9—C101.383 (4)C28—C291.361 (4)
C9—C141.401 (4)C28—H280.9300
C10—C111.381 (4)C29—C301.392 (4)
C10—H100.9300C29—H290.9300
C11—C121.364 (4)
C6—S1—C788.75 (13)C16—C15—H15A110.7
C7—S2—C8102.31 (13)O1—C15—H15B110.7
C24—S3—C23103.19 (12)C16—C15—H15B110.7
C30—S4—C2488.64 (12)H15A—C15—H15B108.8
C7—N1—C1110.3 (2)O2—C16—C15104.9 (2)
C24—N2—C25110.1 (2)O2—C16—H16A110.8
C14—O1—C15117.9 (2)C15—C16—H16A110.8
C17—O2—C16118.58 (19)O2—C16—H16B110.8
C2—C1—N1125.3 (2)C15—C16—H16B110.8
C2—C1—C6119.4 (2)H16A—C16—H16B108.8
N1—C1—C6115.3 (2)O2—C17—C18124.5 (2)
C3—C2—C1119.0 (3)O2—C17—C22115.0 (2)
C3—C2—H2120.5C18—C17—C22120.5 (2)
C1—C2—H2120.5C17—C18—C19119.3 (2)
C2—C3—C4120.9 (3)C17—C18—H18120.3
C2—C3—H3119.6C19—C18—H18120.3
C4—C3—H3119.6C20—C19—C18121.0 (3)
C5—C4—C3121.3 (3)C20—C19—H19119.5
C5—C4—H4119.4C18—C19—H19119.5
C3—C4—H4119.4C19—C20—C21119.2 (2)
C4—C5—C6118.0 (3)C19—C20—H20120.4
C4—C5—H5121.0C21—C20—H20120.4
C6—C5—H5121.0C20—C21—C22121.6 (3)
C5—C6—C1121.5 (3)C20—C21—H21119.2
C5—C6—S1129.4 (2)C22—C21—H21119.2
C1—C6—S1109.18 (19)C21—C22—C17118.3 (2)
N1—C7—S2126.9 (2)C21—C22—C23121.8 (2)
N1—C7—S1116.4 (2)C17—C22—C23119.8 (2)
S2—C7—S1116.72 (16)C22—C23—S3107.34 (17)
C9—C8—S2112.85 (19)C22—C23—H23A110.2
C9—C8—H8A109.0S3—C23—H23A110.2
S2—C8—H8A109.0C22—C23—H23B110.2
C9—C8—H8B109.0S3—C23—H23B110.2
S2—C8—H8B109.0H23A—C23—H23B108.5
H8A—C8—H8B107.8N2—C24—S3120.79 (19)
C10—C9—C14117.8 (3)N2—C24—S4116.25 (19)
C10—C9—C8121.6 (3)S3—C24—S4122.87 (15)
C14—C9—C8120.6 (2)N2—C25—C30115.4 (2)
C11—C10—C9121.3 (3)N2—C25—C26125.1 (2)
C11—C10—H10119.3C30—C25—C26119.5 (2)
C9—C10—H10119.3C27—C26—C25119.1 (3)
C12—C11—C10119.8 (3)C27—C26—H26120.5
C12—C11—H11120.1C25—C26—H26120.5
C10—C11—H11120.1C26—C27—C28120.7 (3)
C11—C12—C13120.7 (3)C26—C27—H27119.7
C11—C12—H12119.7C28—C27—H27119.7
C13—C12—H12119.7C29—C28—C27121.6 (3)
C14—C13—C12119.5 (3)C29—C28—H28119.2
C14—C13—H13120.2C27—C28—H28119.2
C12—C13—H13120.2C28—C29—C30118.0 (3)
O1—C14—C13125.0 (2)C28—C29—H29121.0
O1—C14—C9114.2 (2)C30—C29—H29121.0
C13—C14—C9120.8 (2)C29—C30—C25121.2 (2)
O1—C15—C16105.2 (2)C29—C30—S4129.3 (2)
O1—C15—H15A110.7C25—C30—S4109.55 (19)
C7—N1—C1—C2−178.5 (3)O1—C15—C16—O2178.7 (2)
C7—N1—C1—C62.0 (3)C16—O2—C17—C18−2.8 (4)
N1—C1—C2—C3−178.7 (3)C16—O2—C17—C22178.2 (2)
C6—C1—C2—C30.8 (4)O2—C17—C18—C19−178.1 (2)
C1—C2—C3—C40.3 (4)C22—C17—C18—C190.8 (4)
C2—C3—C4—C5−0.8 (5)C17—C18—C19—C200.2 (4)
C3—C4—C5—C60.3 (5)C18—C19—C20—C21−0.7 (4)
C4—C5—C6—C10.8 (4)C19—C20—C21—C220.3 (4)
C4—C5—C6—S1−178.3 (2)C20—C21—C22—C170.7 (4)
C2—C1—C6—C5−1.4 (4)C20—C21—C22—C23−177.3 (2)
N1—C1—C6—C5178.2 (2)O2—C17—C22—C21177.8 (2)
C2—C1—C6—S1178.0 (2)C18—C17—C22—C21−1.2 (4)
N1—C1—C6—S1−2.5 (3)O2—C17—C22—C23−4.2 (3)
C7—S1—C6—C5−179.0 (3)C18—C17—C22—C23176.8 (2)
C7—S1—C6—C11.8 (2)C21—C22—C23—S3103.3 (2)
C1—N1—C7—S2−178.76 (19)C17—C22—C23—S3−74.7 (3)
C1—N1—C7—S1−0.5 (3)C24—S3—C23—C22167.45 (18)
C8—S2—C7—N1−12.9 (3)C25—N2—C24—S3−176.17 (18)
C8—S2—C7—S1168.86 (15)C25—N2—C24—S40.5 (3)
C6—S1—C7—N1−0.8 (2)C23—S3—C24—N2−162.0 (2)
C6—S1—C7—S2177.66 (16)C23—S3—C24—S421.6 (2)
C7—S2—C8—C9−117.2 (2)C30—S4—C24—N20.1 (2)
S2—C8—C9—C10−108.3 (3)C30—S4—C24—S3176.65 (18)
S2—C8—C9—C1473.8 (3)C24—N2—C25—C30−1.0 (3)
C14—C9—C10—C110.2 (4)C24—N2—C25—C26178.4 (3)
C8—C9—C10—C11−177.8 (3)N2—C25—C26—C27−179.7 (3)
C9—C10—C11—C120.3 (5)C30—C25—C26—C27−0.3 (4)
C10—C11—C12—C13−0.5 (5)C25—C26—C27—C280.0 (5)
C11—C12—C13—C140.2 (5)C26—C27—C28—C29−0.2 (5)
C15—O1—C14—C13−1.7 (4)C27—C28—C29—C300.8 (5)
C15—O1—C14—C9178.8 (2)C28—C29—C30—C25−1.1 (4)
C12—C13—C14—O1−179.1 (3)C28—C29—C30—S4178.0 (2)
C12—C13—C14—C90.3 (4)N2—C25—C30—C29−179.7 (2)
C10—C9—C14—O1179.0 (2)C26—C25—C30—C290.9 (4)
C8—C9—C14—O1−3.0 (4)N2—C25—C30—S41.0 (3)
C10—C9—C14—C13−0.5 (4)C26—C25—C30—S4−178.4 (2)
C8—C9—C14—C13177.5 (3)C24—S4—C30—C29−179.8 (3)
C14—O1—C15—C16176.6 (2)C24—S4—C30—C25−0.6 (2)
C17—O2—C16—C15174.3 (2)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3,and Cg5 are centroids of the S4,C24,N2,C25,C30, C1–C6 and C17–C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg2i0.932.913.727 (3)147
C13—H13···Cg3ii0.932.873.705 (3)149
C18—H18···Cg30.932.813.636 (3)149
C21—H21···Cg2iii0.932.783.457 (3)131
C29—H29···Cg5ii0.932.793.559 (3)141
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC30H24N2O2S4
Mr572.75
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.8194 (6), 10.7740 (8), 14.0716 (9)
α, β, γ (°)82.422 (1), 76.285 (1), 68.993 (1)
V (Å3)1348.32 (16)
Z2
Radiation typeMo Kα
µ (mm−1)0.39
Crystal size (mm)0.35 × 0.32 × 0.30
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.877, 0.893
No. of measured, independent and
observed [I > 2σ(I)] reflections		7093, 4947, 3531
Rint0.022
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.101, 1.01
No. of reflections4947
No. of parameters343
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.24, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg2, Cg3,and Cg5 are centroids of the S4,C24,N2,C25,C30, C1–C6 and C17–C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg2i0.932.913.727 (3)147
C13—H13···Cg3ii0.932.873.705 (3)149
C18—H18···Cg30.932.813.636 (3)149
C21—H21···Cg2iii0.932.783.457 (3)131
C29—H29···Cg5ii0.932.793.559 (3)141
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y+2, −z.
 

Acknowledgements

The authors acknowledge the Fundamental Research Funds for the Central Universities (lzujbky–2010–43) and the Research Foundation for Young Teachers Possessing a Doctoral Degree of Lanzhou University for financial support.

References

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 First citationKumar, R. V., Kumar, V. S. R. S. & Gopal, K. R. (2005). J. Heterocycl. Chem. 42, 153–156.  CAS Google Scholar
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 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSiva, A. & Murugan, E. (2005). J. Mol. Catal. A Chem. 241, 101–110.  Web of Science CrossRef CAS Google Scholar
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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2229
https://doi.org/10.1107/S160053681003062X
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