Bis[2-((4,6-dimethyl­pyrimidin-2-yl){2-[(4,6-dimethyl­pyrimidin-2-yl)sulfan­yl]eth­yl}amino)­eth­yl] disulfide

Wang, G.-Q.; Ma, C.-H.; Li, W.-G.; Li, X.-F.; Ng, S.W.

doi:10.1107/S1600536810035245

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2517

doi:10.1107/S1600536810035245

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Bis[2-((4,6-dimethylpyrimidin-2-yl){2-[(4,6-dimethylpyrimidin-2-yl)sulfanyl]ethyl}amino)ethyl] disulfide

Guo-Qing Wang,^a Cong-Hui Ma,^b ^* Wen-Ge Li,^b Xiao-Feng Li ^b and Seik Weng Ng ^c

^aShanghai Sunvea Chemical Materials Science and Technology Co Ltd, Shanghai 201611, People's Republic of China, ^bInstitute of Marine Materials Science and Engineering, Shanghai Maritime University, Shanghai 201306, People's Republic of China, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 26 August 2010; accepted 1 September 2010; online 8 September 2010)

Bis[2-(4,6-dimethylpyrimidin-2-ylsulfanyl)ethyl]amine under hydrothermal conditions has unexpectedly been transformed into the title compound, C₃₂H₄₄N₁₀S₄. In the title molecule, the zigzag 3,10-diaza-6,7-disulfanyldodecyl skeleton has two dimethylpyrimidinylsulfanyl groups at both ends, and the aza atoms each carry a dimethylpyrimidinyl unit. The N atoms in the skeleton show a planar coordination.

Related literature

For the crystal structures of ligands having two 4,6-dimethylpyridimin-2-ylsulfanyl units linked to a hydrocarbon chain, see: Chen et al. (2007 ); Wang et al. (2007 ); Wu et al. (2007a ,b ).

Experimental

Crystal data

C₃₂H₄₄N₁₀S₄
M_r = 697.01
Triclinic, $[P \overline 1]$
a = 11.7626 (5) Å
b = 12.7672 (6) Å
c = 13.7444 (7) Å
α = 106.382 (4)°
β = 103.276 (4)°
γ = 102.294 (4)°
V = 1840.15 (17) Å³
Z = 2
Cu Kα radiation
μ = 2.67 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire 3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.947, T_max = 1.000
11434 measured reflections
7060 independent reflections
5177 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.252
S = 1.07
7060 reflections
423 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 1.45 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035245/xu5021sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035245/xu5021Isup2.hkl

checkCIF report

Comment top

We are interested in synthesizing flexible ligands having two 4,6-dimethylpyridimin-2-ylsulfanyl units linked to a hydrocarbon chain; compounds such as 2,2'-bis(4,6-dimethylpyrimidn-2-ylsulfanyl)methane (Chen et al., 2007) and its ethane (Wu et al., 2007b), propane (Wu et al., 2007a) and butane (Wang et al., 2007) analogs have been synthesized for the purpose of studying its coordination chemistry in metal adducts. The coordination chemistry can be expanded in bis[2-(4,6-dimethylpyrimidin-2-ysulfanyl)ethyl]amine, whose synthesis has not been reported yet. However, the attempted complexation with copper ions under hydrothermal conditions yielded bis{2-[(4,6-dimethylpyrimidin-1-yl)(4,6-dimethylpyrimidin-1-ylsulfanyl-2-ethyl)amino]ethyl}disulfide (Scheme I, Fig. 1), a more interesting ligand whose exocyclic sulfur and endocyclic nitrogen sites offer many more sites for coordination.

Related literature top

For the crystal structures of ligands having two 4,6-dimethylpyridimin-2-ylsulfanyl units linked to a hydrocarbon chain, see: Chen et al. (2007); Wang et al. (2007); Wu et al. (2007a,b).

Experimental top

Bis[2-(4,6-dimethylpyrimidin-2-ylsulfanyl)ethyl]amine was synthesized from the reaction of bis(2-chloroethyl)ammonium hydrochloride (1.78 g, 0.01 mol) dissolved in ethanol (100 ml) and 4,6-dimethylpyrimidine-2-thiol (2.80 g, 0.02 mol)/sodium hydroxide (0.8 g, 0.02 mol) dissolved in ethanol (200 ml). The solution was heated at 353 K for 8 h. The solvent was removed and the residue was column chromatographed with ethly acetate/petroleum ether (1/1 v/v) as eluent to yield a white powder; yield 63%. The formulation was confirmed by ¹H NMR (CDCl₃, 400 MHz) spectroscopy: 1.36–1.402(m, 1H), 2.274 (d,6H), 2.403–2.426 (d,6H), 2.813–2.871(m, 2H), 3.343–3.380 (m, 2H), 6.279 (s, 1H), 6.715 (s, 1H). This compound has not been reported in the chemical literature yet.

The title compound was the unexpected product obtained in the reaction of bis(2-(4,6-dimethylpyrimidin-2-ylthio)ethyl)amine (0.175 g, 0.5 mmol), copper perchlorate (0.132 g, 0.5 mmol) and water (8 ml). The reactants were heated in a 23-ml Teflon-lined Parr reactor at 413 K for 3 days. The mixture was cooled to room temperature at a rate of 5 K h^-1. The prismatic crystals were collected and washed with water; yield: 40%. MS (ESI) m/z(%): 698.2 (M⁺¹). CH&N elemental analysis, calculated for C₃₂H₄₄N₁₀S₄: C 55.14, H 6.36, N 20.09%. Found: C 55.50, H 6.56, N 19.56%.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₃₂H₄₄N₁₀S₄ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Bis[2-((4,6-dimethylpyrimidin-2-yl){2-[(4,6-dimethylpyrimidin-2- yl)sulfanyl]ethyl}amino)ethyl] disulfide top

Crystal data top

C₃₂H₄₄N₁₀S₄	Z = 2
M_r = 697.01	F(000) = 740
Triclinic, P1	D_x = 1.258 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 11.7626 (5) Å	Cell parameters from 5344 reflections
b = 12.7672 (6) Å	θ = 4.6–74.5°
c = 13.7444 (7) Å	µ = 2.67 mm⁻¹
α = 106.382 (4)°	T = 293 K
β = 103.276 (4)°	Prism, colorless
γ = 102.294 (4)°	0.30 × 0.25 × 0.20 mm
V = 1840.15 (17) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire 3 diffractometer	7060 independent reflections
Radiation source: fine-focus sealed tube	5177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 16.0855 pixels mm^-1	θ_max = 72.6°, θ_min = 4.6°
ω scans	h = −14→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −15→15
T_min = 0.947, T_max = 1.000	l = −16→16
11434 measured reflections

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.252	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1399P)² + 1.4306P] where P = (F_o² + 2F_c²)/3
7060 reflections	(Δ/σ)_max = 0.001
423 parameters	Δρ_max = 1.45 e Å⁻³
4 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

C₃₂H₄₄N₁₀S₄	γ = 102.294 (4)°
M_r = 697.01	V = 1840.15 (17) Å³
Triclinic, P1	Z = 2
a = 11.7626 (5) Å	Cu Kα radiation
b = 12.7672 (6) Å	µ = 2.67 mm⁻¹
c = 13.7444 (7) Å	T = 293 K
α = 106.382 (4)°	0.30 × 0.25 × 0.20 mm
β = 103.276 (4)°

Data collection top

Oxford Diffraction Xcalibur Sapphire 3 diffractometer	7060 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	5177 reflections with I > 2σ(I)
T_min = 0.947, T_max = 1.000	R_int = 0.020
11434 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	4 restraints
wR(F²) = 0.252	H-atom parameters constrained
S = 1.07	Δρ_max = 1.45 e Å⁻³
7060 reflections	Δρ_min = −0.75 e Å⁻³
423 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.74226 (10)	0.71528 (10)	0.39171 (9)	0.0696 (3)
S2	0.57455 (12)	0.67895 (10)	0.41240 (10)	0.0812 (4)
S3	0.96757 (10)	0.65326 (9)	0.03184 (10)	0.0661 (3)
S4	0.36046 (14)	0.95980 (10)	0.78051 (12)	0.0903 (5)
N1	0.6607 (3)	0.6061 (3)	0.1261 (3)	0.0538 (7)
N2	0.5256 (3)	0.4838 (3)	0.1734 (3)	0.0527 (7)
N3	0.6443 (3)	0.4147 (3)	0.0636 (2)	0.0531 (7)
N4	0.9874 (3)	0.8593 (3)	0.1672 (3)	0.0582 (8)
N5	1.0838 (3)	0.8487 (3)	0.0304 (3)	0.0598 (8)
N6	0.6477 (4)	0.9727 (4)	0.6648 (4)	0.0905 (14)
N7	0.7688 (3)	1.0764 (3)	0.5901 (3)	0.0745 (11)
N8	0.6908 (4)	1.1703 (3)	0.7257 (3)	0.0685 (10)
N9	0.3262 (4)	0.7490 (3)	0.6468 (3)	0.0712 (10)
N10	0.1976 (4)	0.7779 (3)	0.7571 (3)	0.0731 (10)
C1	0.7241 (4)	0.7789 (3)	0.2897 (3)	0.0645 (11)
H1A	0.7028	0.8486	0.3162	0.077*
H1B	0.8021	0.8000	0.2770	0.077*
C2	0.6275 (4)	0.7027 (3)	0.1837 (3)	0.0590 (9)
H2A	0.5514	0.6746	0.1972	0.071*
H2B	0.6132	0.7485	0.1392	0.071*
C3	0.6078 (3)	0.4974 (3)	0.1210 (3)	0.0484 (8)
C4	0.4770 (3)	0.3770 (3)	0.1680 (3)	0.0554 (9)
C5	0.3843 (5)	0.3613 (4)	0.2253 (4)	0.0772 (13)
H5A	0.4117	0.4218	0.2932	0.116*
H5B	0.3743	0.2891	0.2358	0.116*
H5C	0.3075	0.3628	0.1837	0.116*
C6	0.5088 (4)	0.2862 (3)	0.1110 (3)	0.0588 (9)
H6	0.4739	0.2122	0.1075	0.071*
C7	0.5939 (3)	0.3083 (3)	0.0593 (3)	0.0537 (9)
C8	0.6332 (5)	0.2155 (4)	−0.0056 (4)	0.0706 (11)
H8A	0.7200	0.2308	0.0227	0.106*
H8B	0.6130	0.2129	−0.0782	0.106*
H8C	0.5918	0.1434	−0.0031	0.106*
C9	0.7418 (3)	0.6247 (3)	0.0630 (3)	0.0537 (9)
H9A	0.7489	0.6996	0.0571	0.064*
H9B	0.7049	0.5684	−0.0084	0.064*
C10	0.8697 (3)	0.6174 (4)	0.1083 (3)	0.0591 (9)
H10A	0.8643	0.5404	0.1081	0.071*
H10B	0.9051	0.6693	0.1816	0.071*
C11	1.0171 (3)	0.8040 (3)	0.0842 (3)	0.0551 (9)
C12	1.0309 (4)	0.9735 (4)	0.2019 (4)	0.0638 (10)
C13	0.9967 (5)	1.0376 (4)	0.2947 (5)	0.0839 (14)
H13A	1.0156	1.0076	0.3511	0.126*
H13B	0.9106	1.0291	0.2729	0.126*
H13C	1.0418	1.1172	0.3196	0.126*
C14	1.1014 (4)	1.0279 (4)	0.1525 (4)	0.0691 (11)
H14	1.1308	1.1073	0.1768	0.083*
C15	1.1274 (4)	0.9623 (4)	0.0662 (4)	0.0611 (10)
C16	1.2025 (4)	1.0147 (4)	0.0081 (4)	0.0761 (13)
H16A	1.1798	0.9639	−0.0643	0.114*
H16B	1.2876	1.0277	0.0425	0.114*
H16C	1.1883	1.0862	0.0088	0.114*
C17	0.5658 (5)	0.8234 (6)	0.4963 (4)	0.112 (2)
H17A	0.5790	0.8783	0.4604	0.134*
H17B	0.4857	0.8149	0.5061	0.134*
C18	0.6604 (5)	0.8636 (5)	0.5998 (4)	0.0878 (15)
H18A	0.7409	0.8759	0.5906	0.105*
H18B	0.6495	0.8076	0.6347	0.105*
C19	0.7040 (5)	1.0778 (4)	0.6585 (4)	0.0789 (14)
C20	0.8330 (4)	1.1790 (4)	0.5960 (3)	0.0659 (11)
C21	0.9099 (5)	1.1770 (6)	0.5229 (5)	0.0984 (18)
H21A	0.8579	1.1487	0.4503	0.148*
H21B	0.9600	1.1280	0.5320	0.148*
H21C	0.9613	1.2530	0.5393	0.148*
C22	0.8282 (4)	1.2782 (4)	0.6648 (4)	0.0668 (11)
H22	0.8742	1.3490	0.6685	0.080*
C23	0.7540 (4)	1.2708 (3)	0.7285 (3)	0.0590 (9)
C24	0.7415 (5)	1.3748 (4)	0.8051 (4)	0.0796 (14)
H24A	0.6594	1.3786	0.7827	0.119*
H24B	0.7977	1.4422	0.8062	0.119*
H24C	0.7595	1.3701	0.8752	0.119*
C25	0.5709 (5)	0.9658 (4)	0.7391 (4)	0.0811 (14)
H25A	0.5534	0.8904	0.7449	0.097*
H25B	0.6147	1.0219	0.8097	0.097*
C26	0.4571 (4)	0.9884 (4)	0.6943 (5)	0.0888 (16)
H26A	0.4172	0.9381	0.6208	0.107*
H26B	0.4727	1.0671	0.6971	0.107*
C27	0.2882 (4)	0.8113 (4)	0.7202 (4)	0.0642 (10)
C28	0.2640 (5)	0.6370 (4)	0.6049 (4)	0.0784 (13)
C29	0.3050 (7)	0.5657 (5)	0.5205 (5)	0.106 (2)
H29A	0.3261	0.6081	0.4762	0.159*
H29B	0.2399	0.4968	0.4776	0.159*
H29C	0.3751	0.5468	0.5536	0.159*
C30	0.1711 (6)	0.5938 (4)	0.6403 (5)	0.0937 (17)
H30	0.1300	0.5159	0.6127	0.112*
C31	0.1387 (5)	0.6670 (5)	0.7175 (5)	0.0860 (15)
C32	0.0362 (7)	0.6270 (6)	0.7581 (7)	0.132 (3)
H32A	0.0588	0.6671	0.8335	0.198*
H32B	0.0197	0.5464	0.7445	0.198*
H32C	−0.0357	0.6419	0.7225	0.198*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0649 (6)	0.0682 (7)	0.0666 (7)	0.0186 (5)	0.0204 (5)	0.0108 (5)
S2	0.0860 (8)	0.0554 (6)	0.0813 (8)	−0.0002 (5)	0.0436 (7)	−0.0057 (5)
S3	0.0617 (6)	0.0514 (5)	0.0835 (7)	0.0110 (4)	0.0360 (5)	0.0143 (5)
S4	0.0995 (9)	0.0567 (6)	0.1033 (10)	−0.0047 (6)	0.0636 (8)	0.0056 (6)
N1	0.0538 (17)	0.0440 (16)	0.0608 (18)	0.0087 (13)	0.0228 (15)	0.0141 (14)
N2	0.0541 (17)	0.0459 (16)	0.0562 (18)	0.0106 (13)	0.0209 (14)	0.0152 (13)
N3	0.0549 (17)	0.0450 (16)	0.0532 (17)	0.0090 (13)	0.0192 (14)	0.0104 (13)
N4	0.0518 (17)	0.0540 (18)	0.068 (2)	0.0145 (14)	0.0229 (15)	0.0174 (15)
N5	0.0507 (17)	0.0581 (19)	0.070 (2)	0.0102 (15)	0.0252 (16)	0.0213 (16)
N6	0.100 (3)	0.061 (2)	0.101 (3)	0.008 (2)	0.057 (3)	0.005 (2)
N7	0.066 (2)	0.075 (2)	0.067 (2)	0.0054 (18)	0.0332 (18)	0.0032 (18)
N8	0.079 (2)	0.0455 (17)	0.073 (2)	0.0055 (16)	0.0401 (19)	0.0054 (16)
N9	0.074 (2)	0.054 (2)	0.077 (2)	0.0105 (17)	0.0210 (19)	0.0160 (18)
N10	0.072 (2)	0.064 (2)	0.078 (2)	0.0025 (18)	0.0258 (19)	0.0287 (19)
C1	0.067 (2)	0.0390 (19)	0.082 (3)	0.0097 (17)	0.031 (2)	0.0108 (18)
C2	0.061 (2)	0.049 (2)	0.071 (2)	0.0184 (17)	0.0242 (19)	0.0219 (18)
C3	0.0443 (17)	0.0452 (18)	0.0489 (19)	0.0073 (14)	0.0111 (14)	0.0135 (15)
C4	0.051 (2)	0.055 (2)	0.056 (2)	0.0070 (16)	0.0172 (17)	0.0192 (17)
C5	0.080 (3)	0.067 (3)	0.096 (3)	0.015 (2)	0.048 (3)	0.033 (3)
C6	0.063 (2)	0.0431 (19)	0.066 (2)	0.0081 (17)	0.0184 (19)	0.0184 (17)
C7	0.054 (2)	0.0458 (19)	0.051 (2)	0.0107 (16)	0.0103 (16)	0.0107 (15)
C8	0.081 (3)	0.050 (2)	0.073 (3)	0.018 (2)	0.026 (2)	0.010 (2)
C9	0.054 (2)	0.051 (2)	0.057 (2)	0.0110 (16)	0.0187 (17)	0.0218 (17)
C10	0.056 (2)	0.055 (2)	0.068 (2)	0.0122 (17)	0.0220 (19)	0.0270 (19)
C11	0.0441 (18)	0.054 (2)	0.065 (2)	0.0122 (16)	0.0185 (17)	0.0168 (18)
C12	0.054 (2)	0.056 (2)	0.072 (3)	0.0145 (18)	0.0188 (19)	0.012 (2)
C13	0.083 (3)	0.068 (3)	0.095 (4)	0.020 (2)	0.041 (3)	0.011 (3)
C14	0.061 (2)	0.047 (2)	0.087 (3)	0.0054 (18)	0.020 (2)	0.016 (2)
C15	0.048 (2)	0.062 (2)	0.073 (3)	0.0114 (17)	0.0171 (18)	0.027 (2)
C16	0.064 (3)	0.078 (3)	0.089 (3)	0.007 (2)	0.028 (2)	0.040 (3)
C17	0.074 (3)	0.142 (6)	0.083 (4)	0.004 (3)	0.042 (3)	−0.008 (4)
C18	0.099 (4)	0.084 (3)	0.088 (4)	0.034 (3)	0.035 (3)	0.031 (3)
C19	0.082 (3)	0.056 (2)	0.085 (3)	0.000 (2)	0.047 (3)	0.002 (2)
C20	0.046 (2)	0.090 (3)	0.061 (2)	0.012 (2)	0.0162 (18)	0.032 (2)
C21	0.078 (3)	0.140 (5)	0.105 (4)	0.038 (3)	0.053 (3)	0.059 (4)
C22	0.054 (2)	0.064 (3)	0.078 (3)	0.0054 (19)	0.015 (2)	0.031 (2)
C23	0.055 (2)	0.050 (2)	0.061 (2)	0.0077 (17)	0.0109 (18)	0.0150 (17)
C24	0.075 (3)	0.044 (2)	0.100 (4)	0.008 (2)	0.020 (3)	0.009 (2)
C25	0.122 (4)	0.055 (2)	0.060 (3)	0.028 (3)	0.016 (3)	0.018 (2)
C26	0.071 (3)	0.058 (3)	0.124 (5)	0.009 (2)	0.011 (3)	0.036 (3)
C27	0.064 (2)	0.054 (2)	0.069 (3)	0.0066 (19)	0.021 (2)	0.022 (2)
C28	0.082 (3)	0.053 (2)	0.088 (3)	0.014 (2)	0.013 (3)	0.022 (2)
C29	0.125 (5)	0.063 (3)	0.107 (4)	0.026 (3)	0.023 (4)	0.008 (3)
C30	0.104 (4)	0.050 (3)	0.104 (4)	−0.004 (3)	0.019 (3)	0.024 (3)
C31	0.088 (3)	0.065 (3)	0.091 (4)	−0.005 (3)	0.022 (3)	0.032 (3)
C32	0.127 (6)	0.103 (5)	0.149 (6)	−0.024 (4)	0.059 (5)	0.048 (5)

Geometric parameters (Å, º) top

S1—C1	1.802 (5)	C9—H9B	0.9700
S1—S2	2.0323 (17)	C10—H10A	0.9700
S2—C17	1.918 (7)	C10—H10B	0.9700
S3—C11	1.764 (4)	C12—C14	1.382 (6)
S3—C10	1.801 (4)	C12—C13	1.499 (6)
S4—C27	1.763 (4)	C13—H13A	0.9600
S4—C26	1.874 (6)	C13—H13B	0.9600
N1—C3	1.369 (5)	C13—H13C	0.9600
N1—C2	1.449 (5)	C14—C15	1.385 (6)
N1—C9	1.456 (5)	C14—H14	0.9300
N2—C4	1.335 (5)	C15—C16	1.497 (6)
N2—C3	1.343 (5)	C16—H16A	0.9600
N3—C7	1.339 (5)	C16—H16B	0.9600
N3—C3	1.342 (5)	C16—H16C	0.9600
N4—C11	1.324 (5)	C17—C18	1.464 (6)
N4—C12	1.339 (5)	C17—H17A	0.9700
N5—C15	1.331 (5)	C17—H17B	0.9700
N5—C11	1.343 (5)	C18—H18A	0.9700
N6—C19	1.399 (6)	C18—H18B	0.9700
N6—C18	1.486 (7)	C20—C22	1.371 (6)
N6—C25	1.520 (7)	C20—C21	1.497 (6)
N7—C20	1.336 (6)	C21—H21A	0.9600
N7—C19	1.338 (6)	C21—H21B	0.9600
N8—C23	1.325 (5)	C21—H21C	0.9600
N8—C19	1.342 (5)	C22—C23	1.378 (6)
N9—C27	1.324 (6)	C22—H22	0.9300
N9—C28	1.345 (6)	C23—C24	1.503 (6)
N10—C27	1.324 (6)	C24—H24A	0.9600
N10—C31	1.325 (6)	C24—H24B	0.9600
C1—C2	1.526 (5)	C24—H24C	0.9600
C1—H1A	0.9700	C25—C26	1.464 (6)
C1—H1B	0.9700	C25—H25A	0.9700
C2—H2A	0.9700	C25—H25B	0.9700
C2—H2B	0.9700	C26—H26A	0.9700
C4—C6	1.380 (6)	C26—H26B	0.9700
C4—C5	1.498 (6)	C28—C30	1.369 (8)
C5—H5A	0.9600	C28—C29	1.501 (8)
C5—H5B	0.9600	C29—H29A	0.9600
C5—H5C	0.9600	C29—H29B	0.9600
C6—C7	1.380 (6)	C29—H29C	0.9600
C6—H6	0.9300	C30—C31	1.387 (8)
C7—C8	1.497 (5)	C30—H30	0.9300
C8—H8A	0.9600	C31—C32	1.495 (8)
C8—H8B	0.9600	C32—H32A	0.9600
C8—H8C	0.9600	C32—H32B	0.9600
C9—C10	1.524 (5)	C32—H32C	0.9600
C9—H9A	0.9700

C1—S1—S2	104.28 (16)	N5—C15—C14	120.6 (4)
C17—S2—S1	104.44 (18)	N5—C15—C16	117.3 (4)
C11—S3—C10	102.6 (2)	C14—C15—C16	122.1 (4)
C27—S4—C26	102.5 (2)	C15—C16—H16A	109.5
C3—N1—C2	121.5 (3)	C15—C16—H16B	109.5
C3—N1—C9	119.8 (3)	H16A—C16—H16B	109.5
C2—N1—C9	118.3 (3)	C15—C16—H16C	109.5
C4—N2—C3	116.0 (3)	H16A—C16—H16C	109.5
C7—N3—C3	116.3 (3)	H16B—C16—H16C	109.5
C11—N4—C12	115.6 (4)	C18—C17—S2	108.2 (5)
C15—N5—C11	116.0 (4)	C18—C17—H17A	110.0
C19—N6—C18	121.8 (4)	S2—C17—H17A	110.0
C19—N6—C25	121.0 (4)	C18—C17—H17B	110.0
C18—N6—C25	117.2 (4)	S2—C17—H17B	110.0
C20—N7—C19	115.3 (4)	H17A—C17—H17B	108.4
C23—N8—C19	116.3 (4)	C17—C18—N6	107.1 (5)
C27—N9—C28	115.1 (4)	C17—C18—H18A	110.3
C27—N10—C31	115.9 (5)	N6—C18—H18A	110.3
C2—C1—S1	114.9 (3)	C17—C18—H18B	110.3
C2—C1—H1A	108.5	N6—C18—H18B	110.3
S1—C1—H1A	108.5	H18A—C18—H18B	108.6
C2—C1—H1B	108.5	N7—C19—N8	126.8 (4)
S1—C1—H1B	108.5	N7—C19—N6	117.4 (4)
H1A—C1—H1B	107.5	N8—C19—N6	115.7 (4)
N1—C2—C1	113.8 (3)	N7—C20—C22	121.7 (4)
N1—C2—H2A	108.8	N7—C20—C21	115.1 (5)
C1—C2—H2A	108.8	C22—C20—C21	123.2 (5)
N1—C2—H2B	108.8	C20—C21—H21A	109.5
C1—C2—H2B	108.8	C20—C21—H21B	109.5
H2A—C2—H2B	107.7	H21A—C21—H21B	109.5
N3—C3—N2	126.5 (3)	C20—C21—H21C	109.5
N3—C3—N1	116.0 (3)	H21A—C21—H21C	109.5
N2—C3—N1	117.5 (3)	H21B—C21—H21C	109.5
N2—C4—C6	121.8 (4)	C20—C22—C23	118.6 (4)
N2—C4—C5	116.2 (4)	C20—C22—H22	120.7
C6—C4—C5	122.0 (4)	C23—C22—H22	120.7
C4—C5—H5A	109.5	N8—C23—C22	121.0 (4)
C4—C5—H5B	109.5	N8—C23—C24	116.6 (4)
H5A—C5—H5B	109.5	C22—C23—C24	122.4 (4)
C4—C5—H5C	109.5	C23—C24—H24A	109.5
H5A—C5—H5C	109.5	C23—C24—H24B	109.5
H5B—C5—H5C	109.5	H24A—C24—H24B	109.5
C4—C6—C7	118.2 (4)	C23—C24—H24C	109.5
C4—C6—H6	120.9	H24A—C24—H24C	109.5
C7—C6—H6	120.9	H24B—C24—H24C	109.5
N3—C7—C6	121.3 (3)	C26—C25—N6	107.6 (4)
N3—C7—C8	116.5 (4)	C26—C25—H25A	110.2
C6—C7—C8	122.2 (4)	N6—C25—H25A	110.2
C7—C8—H8A	109.5	C26—C25—H25B	110.2
C7—C8—H8B	109.5	N6—C25—H25B	110.2
H8A—C8—H8B	109.5	H25A—C25—H25B	108.5
C7—C8—H8C	109.5	C25—C26—S4	104.7 (4)
H8A—C8—H8C	109.5	C25—C26—H26A	110.8
H8B—C8—H8C	109.5	S4—C26—H26A	110.8
N1—C9—C10	114.3 (3)	C25—C26—H26B	110.8
N1—C9—H9A	108.7	S4—C26—H26B	110.8
C10—C9—H9A	108.7	H26A—C26—H26B	108.9
N1—C9—H9B	108.7	N10—C27—N9	128.7 (4)
C10—C9—H9B	108.7	N10—C27—S4	111.4 (3)
H9A—C9—H9B	107.6	N9—C27—S4	119.9 (3)
C9—C10—S3	111.4 (3)	N9—C28—C30	120.5 (5)
C9—C10—H10A	109.4	N9—C28—C29	115.7 (5)
S3—C10—H10A	109.4	C30—C28—C29	123.8 (5)
C9—C10—H10B	109.4	C28—C29—H29A	109.5
S3—C10—H10B	109.4	C28—C29—H29B	109.5
H10A—C10—H10B	108.0	H29A—C29—H29B	109.5
N4—C11—N5	127.8 (4)	C28—C29—H29C	109.5
N4—C11—S3	120.2 (3)	H29A—C29—H29C	109.5
N5—C11—S3	111.9 (3)	H29B—C29—H29C	109.5
N4—C12—C14	121.1 (4)	C28—C30—C31	119.5 (5)
N4—C12—C13	116.3 (4)	C28—C30—H30	120.2
C14—C12—C13	122.6 (4)	C31—C30—H30	120.2
C12—C13—H13A	109.5	N10—C31—C30	120.3 (5)
C12—C13—H13B	109.5	N10—C31—C32	117.0 (6)
H13A—C13—H13B	109.5	C30—C31—C32	122.8 (5)
C12—C13—H13C	109.5	C31—C32—H32A	109.5
H13A—C13—H13C	109.5	C31—C32—H32B	109.5
H13B—C13—H13C	109.5	H32A—C32—H32B	109.5
C12—C14—C15	118.9 (4)	C31—C32—H32C	109.5
C12—C14—H14	120.6	H32A—C32—H32C	109.5
C15—C14—H14	120.6	H32B—C32—H32C	109.5

C1—S1—S2—C17	−77.4 (3)	S1—S2—C17—C18	−63.6 (5)
S2—S1—C1—C2	−59.5 (3)	S2—C17—C18—N6	−177.4 (4)
C3—N1—C2—C1	105.5 (4)	C19—N6—C18—C17	−85.7 (7)
C9—N1—C2—C1	−81.3 (4)	C25—N6—C18—C17	94.5 (6)
S1—C1—C2—N1	−69.4 (4)	C20—N7—C19—N8	5.0 (8)
C7—N3—C3—N2	−0.5 (6)	C20—N7—C19—N6	−172.1 (5)
C7—N3—C3—N1	179.3 (3)	C23—N8—C19—N7	−4.0 (8)
C4—N2—C3—N3	0.7 (6)	C23—N8—C19—N6	173.2 (5)
C4—N2—C3—N1	−179.1 (3)	C18—N6—C19—N7	1.0 (8)
C2—N1—C3—N3	178.8 (3)	C25—N6—C19—N7	−179.2 (5)
C9—N1—C3—N3	5.8 (5)	C18—N6—C19—N8	−176.5 (5)
C2—N1—C3—N2	−1.3 (5)	C25—N6—C19—N8	3.4 (8)
C9—N1—C3—N2	−174.3 (3)	C19—N7—C20—C22	−2.4 (7)
C3—N2—C4—C6	−0.6 (6)	C19—N7—C20—C21	177.2 (5)
C3—N2—C4—C5	−179.4 (4)	N7—C20—C22—C23	−0.7 (7)
N2—C4—C6—C7	0.4 (6)	C21—C20—C22—C23	179.7 (4)
C5—C4—C6—C7	179.1 (4)	C19—N8—C23—C22	0.4 (7)
C3—N3—C7—C6	0.3 (5)	C19—N8—C23—C24	−178.9 (4)
C3—N3—C7—C8	179.3 (3)	C20—C22—C23—N8	1.8 (7)
C4—C6—C7—N3	−0.2 (6)	C20—C22—C23—C24	−179.1 (4)
C4—C6—C7—C8	−179.2 (4)	C19—N6—C25—C26	71.8 (6)
C3—N1—C9—C10	−77.2 (4)	C18—N6—C25—C26	−108.3 (5)
C2—N1—C9—C10	109.6 (4)	N6—C25—C26—S4	173.0 (3)
N1—C9—C10—S3	−175.1 (3)	C27—S4—C26—C25	−86.1 (4)
C11—S3—C10—C9	82.3 (3)	C31—N10—C27—N9	1.8 (8)
C12—N4—C11—N5	−0.9 (6)	C31—N10—C27—S4	−179.1 (4)
C12—N4—C11—S3	179.1 (3)	C28—N9—C27—N10	−0.2 (7)
C15—N5—C11—N4	1.5 (6)	C28—N9—C27—S4	−179.3 (4)
C15—N5—C11—S3	−178.5 (3)	C26—S4—C27—N10	−167.7 (3)
C10—S3—C11—N4	5.5 (4)	C26—S4—C27—N9	11.5 (4)
C10—S3—C11—N5	−174.5 (3)	C27—N9—C28—C30	−1.7 (7)
C11—N4—C12—C14	0.4 (6)	C27—N9—C28—C29	179.1 (5)
C11—N4—C12—C13	179.1 (4)	N9—C28—C30—C31	2.0 (9)
N4—C12—C14—C15	−0.4 (7)	C29—C28—C30—C31	−178.9 (5)
C13—C12—C14—C15	−179.1 (4)	C27—N10—C31—C30	−1.4 (8)
C11—N5—C15—C14	−1.4 (6)	C27—N10—C31—C32	179.8 (6)
C11—N5—C15—C16	179.8 (4)	C28—C30—C31—N10	−0.3 (9)
C12—C14—C15—N5	1.0 (7)	C28—C30—C31—C32	178.4 (6)
C12—C14—C15—C16	179.7 (4)

Experimental details

Crystal data
Chemical formula	C₃₂H₄₄N₁₀S₄
M_r	697.01
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	11.7626 (5), 12.7672 (6), 13.7444 (7)
α, β, γ (°)	106.382 (4), 103.276 (4), 102.294 (4)
V (Å³)	1840.15 (17)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.67
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire 3 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.947, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11434, 7060, 5177
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.252, 1.07
No. of reflections	7060
No. of parameters	423
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.45, −0.75

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the Special Foundation for Nano Technology of the Shanghai Committee for S&T (1052 nm00600), the Foundation of the S&T Program of Shanghai Maritime University (20100128), the State Key Laboratory of Pollution Control and Resource Reuse Foundation (PCRRF09001) and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Chen, S.-K., Li, L., Tian, L. & Wu, J.-Y. (2007). Acta Cryst. E63, o1126–o1127. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, M., Cheng, L.-H. & Wang, A.-M. (2007). Acta Cryst. E63, o3296. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, G.-H., Liu, T.-B., Peng, Y.-F. & Wu, G.-Z. (2007a). Acta Cryst. E63, o4349. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wu, G.-H., Wu, X.-M., Zhang, J.-P. & Liu, T.-B. (2007b). Acta Cryst. E63, o3776. Web of Science CSD CrossRef IUCr Journals Google Scholar

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