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Acta Cryst. (2007). E63, o3370    [ doi:10.1107/S1600536807029157 ]

2-[3,5-Bis(5,6-dihydro-4H-1,3-thiazin-2-ylsulfanylmethyl)-2,4,6-trimethylbenzylsulfanyl]-5,6-dihydro-4H-1,3-thiazine

W. Wang, B. Zhao, D. Liang, Y.-L. Feng and X.-Y. Fan

Abstract top

The title compound, C24H33N3S6, contains three 1,3-thiazin-2-ylsulfanyl groups. Two are located on the same side of the planar benzene ring and the other is on the opposite side. The three C atoms in one of the heterocyclic rings are disordered over two sites in an approximately 0.54:0.46 ratio.

Comment top

Thioethers are often used as bridging ligands in construction of coordination polymers with soft metal ions. Now, we have a new thiazinyl derivative and present here the crystal structure of 2-(3,5-bis((5,6-dihydro-4H-1,3-thiazin-2-ylthio)methyl)-2,4,6- trimethylbenzylthio)-5,6-dihydro-4H-1,3-thiazine, (I).

There are three 1,3-thiazinyl sulfanyl groups in this molecule. Two 1,3-thiazinyl sulfanyl groups are located on the same side of the planar benzene ring and the other is on the opposite side. In the thiazinyl ring, the C11 atom has an distorted trigonal geometry, with S2—C11—S1 = 108.22 (2) and N1—C11—S2 = 130.7 (2)° deviating significantly from the ideal sp2 value of 120°. The similar results are observed in the other two thiazinyl rings. The C22, C23 and C24 atoms in the thiazinyl ring attached to the S5 atom are disordered over two sites [occupancies 0.462 (2) and 0.538 (2)]. The three methyl groups are almost coplanar with the benzene ring, with an r. m. s. derivation of 0.0272 Å.

Due to π-π conjugation, the Csp2—S bonds distances[S2—C11 = 1.764 (3) Å, S4—C16 = 1.773 (3)Å and S5—C21 = 1.759 (3) Å] are significantly shorter than the Csp3—S bonds distances [S1—C10 = 1.824 (3) Å, S3—C15 = 1.828 (3)Å and S5—C20 = 1.822 (3) Å]. These values are comparable with those in the literature (Wang et al., 2004, 2005). The other bond distances are within normal ranges (Allen et al., 1987).

Related literature top

For related literature, see: Allen et al. (1987); Wang et al. (2004, 2005); Jacobson (1998).

Experimental top

A solution of 1-bromo-3,5-bis(bromomethyl)-2,4,6-trimethylbenzene (0.45 g, 1 mmol) in ethanol (5 ml) was added dropwise to a mixture of 5,6-dihydro-4H-1,3-thiazine-2-thiol (0.45 g, 3.4 mmol), KOH (0.19 g, 3.4 mmol) and ethanol (15 ml). The reaction mixture was then stirred for 48 h at room temperature. Then the precipitate was filtered off, washed with water and recrystallized from ethanol and water (yield 62%, m.p. 455–457 K). Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a CH2Cl2 solution.

Refinement top

All H atoms were positioned geometrically and refined as riding with C—H = 0.98 and 0.99 Å). For the CH groups, Uiso(H) values are set equal to 1.2Ueq (carrier atom) and for the methyl groups they are set equal to 1.5Ueq (carrier atom). The C22, C23 and C24 atoms in the thiazinyl ring attached to the S5 atom are disordered over two sites [occupancies 0.462 (2) and 0.538 (2)].

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
2-[3,5-Bis(5,6-dihydro-4H-1,3-thiazin-2-ylsulfanylmethyl)-2,4,6- trimethylbenzylsulfanyl]-5,6-dihydro-4H-1,3-thiazine top
Crystal data top
C24H33N3S6F(000) = 1176
Mr = 555.89Dx = 1.400 Mg m−3
Monoclinic, P21/cMelting point: 455 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 17.146 (3) ÅCell parameters from 5347 reflections
b = 10.123 (2) Åθ = 2.3–24.5°
c = 17.408 (4) ŵ = 0.58 mm−1
β = 119.20 (3)°T = 113 K
V = 2637.6 (9) Å3Block, colourless
Z = 40.20 × 0.18 × 0.02 mm
Data collection top
Rigaku Saturn
diffractometer		5178 independent reflections
Radiation source: rotating anode4350 reflections with I > 2σ(I)
confocalRint = 0.043
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 1.4°
ω scansh = −21→20
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −12→12
Tmin = 0.900, Tmax = 0.989l = −13→21
17102 measured reflections
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0604P)2 + 3.1576P]
where P = (Fo2 + 2Fc2)/3
5178 reflections(Δ/σ)max = 0.002
329 parametersΔρmax = 1.17 e Å−3
7 restraintsΔρmin = −0.42 e Å−3
Crystal data top
C24H33N3S6V = 2637.6 (9) Å3
Mr = 555.89Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.146 (3) ŵ = 0.58 mm−1
b = 10.123 (2) ÅT = 113 K
c = 17.408 (4) Å0.20 × 0.18 × 0.02 mm
β = 119.20 (3)°
Data collection top
Rigaku Saturn
diffractometer		5178 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4350 reflections with I > 2σ(I)
Tmin = 0.900, Tmax = 0.989Rint = 0.043
17102 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.139Δρmax = 1.17 e Å−3
S = 1.08Δρmin = −0.42 e Å−3
5178 reflectionsAbsolute structure: ?
329 parametersFlack parameter: ?
7 restraintsRogers parameter: ?
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*/UeqOcc. (<1)
S10.22603 (7)0.49261 (8)1.16480 (5)0.0391 (2)
S20.21116 (6)0.41297 (8)1.31502 (5)0.0341 (2)
S30.40459 (7)0.67273 (8)0.89432 (7)0.0443 (3)
S40.51695 (7)0.75283 (8)0.82245 (6)0.0389 (2)
S50.04801 (6)0.40067 (8)0.72402 (5)0.0414 (3)
S6−0.01276 (6)0.28553 (9)0.55715 (6)0.0378 (2)
N10.2901 (2)0.2620 (3)1.24070 (19)0.0378 (7)
N20.44422 (17)0.9257 (2)0.89238 (17)0.0272 (6)
N3−0.09428 (18)0.5017 (3)0.58476 (16)0.0305 (6)
C10.2251 (2)0.5004 (3)1.00786 (18)0.0262 (7)
C20.2894 (2)0.5851 (3)1.00776 (19)0.0265 (7)
C30.2683 (2)0.6612 (3)0.93296 (19)0.0242 (6)
C40.1851 (2)0.6473 (3)0.85736 (18)0.0229 (6)
C50.1201 (2)0.5656 (3)0.85905 (18)0.0220 (6)
C60.1388 (2)0.4930 (3)0.93487 (19)0.0247 (6)
C70.0681 (2)0.4062 (3)0.9370 (2)0.0365 (8)
H7A0.06770.32000.91120.055*
H7B0.00950.44810.90320.055*
H7C0.08150.39430.99810.055*
C80.3816 (2)0.5939 (4)1.0879 (2)0.0440 (9)
H8A0.37610.62141.13910.066*
H8B0.41760.65861.07710.066*
H8C0.41060.50721.09940.066*
C90.1652 (3)0.7181 (3)0.7734 (2)0.0372 (8)
H9A0.12910.79680.76660.056*
H9B0.13220.65900.72310.056*
H9C0.22140.74450.77590.056*
C100.2502 (2)0.4094 (3)1.0858 (2)0.0327 (7)
H10A0.31450.38721.11390.039*
H10B0.21550.32631.06570.039*
C110.2507 (2)0.3647 (3)1.24276 (19)0.0278 (7)
C120.3113 (3)0.1601 (4)1.3058 (3)0.0510 (11)
H12A0.36510.11251.31370.061*
H12B0.26140.09591.28310.061*
C130.3284 (3)0.2093 (4)1.3963 (2)0.0487 (10)
H13A0.34450.13311.43680.058*
H13B0.37990.27071.42050.058*
C140.2501 (2)0.2779 (3)1.3929 (2)0.0352 (8)
H14A0.26670.31231.45210.042*
H14B0.20100.21351.37620.042*
C150.3350 (2)0.7569 (3)0.9320 (2)0.0351 (8)
H15A0.37310.79270.99180.042*
H15B0.30330.83160.89220.042*
C160.4551 (2)0.8098 (3)0.8730 (2)0.0264 (6)
C170.4867 (2)1.0354 (3)0.8727 (2)0.0298 (7)
H17A0.49251.11060.91150.036*
H17B0.44741.06390.81120.036*
C180.5787 (2)1.0031 (3)0.8843 (2)0.0288 (7)
H18A0.60601.08480.87680.035*
H18B0.61750.96990.94470.035*
C190.5739 (2)0.9015 (3)0.8193 (2)0.0318 (7)
H19A0.63520.87860.83220.038*
H19B0.54210.93950.75930.038*
C200.0312 (2)0.5463 (3)0.77578 (19)0.0298 (7)
H20A0.01620.62430.73670.036*
H20B−0.01740.53150.79000.036*
C21−0.0352 (2)0.4136 (3)0.61307 (19)0.0249 (6)
C22−0.1721 (8)0.5025 (18)0.4950 (7)0.029 (3)0.462 (15)
H22A−0.18770.59510.47520.035*0.462 (15)
H22B−0.22380.46230.49680.035*0.462 (15)
C23−0.1552 (8)0.4282 (10)0.4290 (6)0.038 (3)0.462 (15)
H23A−0.21190.42180.37270.046*0.462 (15)
H23B−0.11230.47890.41790.046*0.462 (15)
C24−0.1187 (7)0.2907 (10)0.4594 (6)0.048 (3)0.462 (15)
H24A−0.11340.24600.41160.058*0.462 (15)
H24B−0.16220.24020.46960.058*0.462 (15)
C22'−0.1523 (9)0.5088 (14)0.4878 (7)0.035 (3)0.538 (15)
H22C−0.12160.56280.46310.042*0.538 (15)
H22D−0.20820.55520.47490.042*0.538 (15)
C23'−0.1763 (5)0.3763 (11)0.4411 (6)0.037 (2)0.538 (15)
H23C−0.20090.31730.46940.045*0.538 (15)
H23D−0.22260.38870.37890.045*0.538 (15)
C24'−0.0947 (6)0.3143 (11)0.4453 (4)0.039 (2)0.538 (15)
H24C−0.06990.37360.41730.046*0.538 (15)
H24D−0.11110.22970.41260.046*0.538 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0654 (6)0.0283 (4)0.0286 (4)0.0160 (4)0.0268 (4)0.0070 (3)
S20.0400 (5)0.0332 (4)0.0363 (4)0.0023 (4)0.0244 (4)0.0006 (3)
S30.0469 (6)0.0207 (4)0.0842 (7)−0.0071 (4)0.0468 (5)−0.0085 (4)
S40.0542 (6)0.0262 (4)0.0516 (5)0.0010 (4)0.0378 (5)−0.0066 (4)
S50.0462 (6)0.0280 (4)0.0292 (4)0.0092 (4)0.0021 (4)−0.0067 (3)
S60.0474 (6)0.0332 (5)0.0387 (5)0.0019 (4)0.0258 (4)−0.0067 (3)
N10.0500 (19)0.0335 (16)0.0406 (16)0.0104 (14)0.0305 (14)0.0115 (12)
N20.0223 (14)0.0218 (13)0.0410 (15)−0.0026 (10)0.0183 (11)−0.0038 (10)
N30.0304 (15)0.0355 (15)0.0217 (12)0.0004 (12)0.0098 (11)−0.0069 (10)
C10.0358 (18)0.0241 (15)0.0212 (14)0.0040 (13)0.0158 (13)0.0007 (11)
C20.0299 (17)0.0197 (14)0.0250 (15)−0.0009 (12)0.0095 (13)−0.0038 (11)
C30.0250 (16)0.0161 (14)0.0330 (16)−0.0027 (12)0.0154 (13)−0.0032 (11)
C40.0330 (17)0.0174 (14)0.0240 (14)0.0023 (12)0.0184 (13)0.0017 (11)
C50.0243 (16)0.0211 (14)0.0210 (14)0.0000 (12)0.0113 (12)−0.0019 (11)
C60.0323 (17)0.0219 (15)0.0258 (15)−0.0012 (13)0.0188 (13)−0.0018 (11)
C70.038 (2)0.0372 (19)0.0442 (19)−0.0047 (15)0.0281 (16)0.0030 (15)
C80.038 (2)0.0313 (19)0.042 (2)−0.0040 (16)0.0031 (16)0.0008 (15)
C90.054 (2)0.0321 (18)0.0286 (16)−0.0043 (16)0.0223 (16)0.0048 (13)
C100.044 (2)0.0265 (16)0.0309 (16)0.0085 (15)0.0208 (15)0.0032 (12)
C110.0289 (17)0.0292 (16)0.0263 (15)−0.0002 (13)0.0144 (13)0.0039 (12)
C120.069 (3)0.0296 (19)0.078 (3)0.0285 (19)0.053 (2)0.0235 (18)
C130.044 (2)0.065 (3)0.043 (2)0.013 (2)0.0264 (18)0.0299 (19)
C140.044 (2)0.0371 (19)0.0273 (16)−0.0063 (16)0.0199 (15)−0.0015 (13)
C150.0375 (19)0.0236 (16)0.053 (2)−0.0064 (14)0.0288 (17)−0.0063 (14)
C160.0228 (16)0.0238 (16)0.0330 (16)−0.0010 (12)0.0140 (13)−0.0026 (12)
C170.0305 (17)0.0217 (15)0.0411 (18)0.0007 (13)0.0206 (14)−0.0002 (13)
C180.0281 (17)0.0263 (16)0.0354 (17)0.0023 (13)0.0182 (14)0.0026 (12)
C190.0309 (18)0.0360 (18)0.0352 (17)0.0037 (14)0.0213 (14)0.0031 (13)
C200.0282 (17)0.0282 (16)0.0286 (16)0.0021 (13)0.0105 (13)−0.0027 (12)
C210.0254 (16)0.0256 (15)0.0264 (15)−0.0055 (13)0.0146 (13)−0.0041 (11)
C220.018 (6)0.049 (6)0.018 (4)0.008 (4)0.008 (4)−0.007 (4)
C230.051 (6)0.035 (5)0.030 (4)−0.009 (4)0.020 (4)−0.011 (4)
C240.097 (9)0.036 (5)0.030 (5)0.007 (6)0.045 (6)0.002 (4)
C22'0.025 (6)0.050 (5)0.031 (5)0.008 (4)0.015 (4)−0.003 (4)
C23'0.028 (4)0.049 (6)0.032 (4)−0.012 (4)0.012 (3)−0.007 (4)
C24'0.059 (5)0.049 (5)0.010 (3)0.001 (4)0.019 (3)−0.006 (3)
Geometric parameters (Å, °) top
S1—C111.772 (3)C9—H9C0.9800
S1—C101.824 (3)C10—H10A0.9900
S2—C111.764 (3)C10—H10B0.9900
S2—C141.808 (3)C12—C131.537 (6)
S3—C161.768 (3)C12—H12A0.9900
S3—C151.828 (3)C12—H12B0.9900
S4—C161.773 (3)C13—C141.487 (5)
S4—C191.809 (3)C13—H13A0.9900
S5—C211.759 (3)C13—H13B0.9900
S5—C201.822 (3)C14—H14A0.9900
S6—C211.773 (3)C14—H14B0.9900
S6—C241.784 (8)C15—H15A0.9900
S6—C24'1.784 (6)C15—H15B0.9900
N1—C111.250 (4)C17—C181.525 (4)
N1—C121.442 (4)C17—H17A0.9900
N2—C161.259 (4)C17—H17B0.9900
N2—C171.458 (4)C18—C191.502 (4)
N3—C211.256 (4)C18—H18A0.9900
N3—C221.478 (11)C18—H18B0.9900
N3—C22'1.486 (10)C19—H19A0.9900
C1—C21.397 (4)C19—H19B0.9900
C1—C61.406 (4)C20—H20A0.9900
C1—C101.519 (4)C20—H20B0.9900
C2—C31.400 (4)C22—C231.515 (9)
C2—C81.517 (4)C22—H22A0.9900
C3—C41.398 (4)C22—H22B0.9900
C3—C151.506 (4)C23—C241.511 (9)
C4—C51.399 (4)C23—H23A0.9900
C4—C91.511 (4)C23—H23B0.9900
C5—C61.405 (4)C24—H24A0.9900
C5—C201.519 (4)C24—H24B0.9900
C6—C71.511 (4)C22'—C23'1.518 (9)
C7—H7A0.9800C22'—H22C0.9900
C7—H7B0.9800C22'—H22D0.9900
C7—H7C0.9800C23'—C24'1.502 (8)
C8—H8A0.9800C23'—H23C0.9900
C8—H8B0.9800C23'—H23D0.9900
C8—H8C0.9800C24'—H24C0.9900
C9—H9A0.9800C24'—H24D0.9900
C9—H9B0.9800
C11—S1—C10100.53 (15)S2—C14—H14B109.1
C11—S2—C14101.23 (15)H14A—C14—H14B107.9
C16—S3—C15100.44 (15)C3—C15—S3109.7 (2)
C16—S4—C19101.96 (15)C3—C15—H15A109.7
C21—S5—C20104.09 (14)S3—C15—H15A109.7
C21—S6—C2496.3 (4)C3—C15—H15B109.7
C21—S6—C24'102.3 (3)S3—C15—H15B109.7
C24—S6—C24'20.1 (3)H15A—C15—H15B108.2
C11—N1—C12120.4 (3)N2—C16—S3121.6 (2)
C16—N2—C17119.4 (3)N2—C16—S4129.7 (2)
C21—N3—C22123.9 (6)S3—C16—S4108.78 (16)
C21—N3—C22'116.4 (6)N2—C17—C18114.1 (3)
C22—N3—C22'16.3 (8)N2—C17—H17A108.7
C2—C1—C6121.0 (3)C18—C17—H17A108.7
C2—C1—C10119.6 (3)N2—C17—H17B108.7
C6—C1—C10119.3 (3)C18—C17—H17B108.7
C1—C2—C3119.5 (3)H17A—C17—H17B107.6
C1—C2—C8120.2 (3)C19—C18—C17112.0 (3)
C3—C2—C8120.3 (3)C19—C18—H18A109.2
C4—C3—C2120.1 (3)C17—C18—H18A109.2
C4—C3—C15119.1 (3)C19—C18—H18B109.2
C2—C3—C15120.8 (3)C17—C18—H18B109.2
C3—C4—C5119.8 (3)H18A—C18—H18B107.9
C3—C4—C9120.5 (3)C18—C19—S4112.3 (2)
C5—C4—C9119.7 (3)C18—C19—H19A109.1
C4—C5—C6120.7 (3)S4—C19—H19A109.1
C4—C5—C20119.6 (3)C18—C19—H19B109.1
C6—C5—C20119.4 (3)S4—C19—H19B109.1
C5—C6—C1118.5 (3)H19A—C19—H19B107.9
C5—C6—C7120.7 (3)C5—C20—S5104.4 (2)
C1—C6—C7120.8 (3)C5—C20—H20A110.9
C6—C7—H7A109.5S5—C20—H20A110.9
C6—C7—H7B109.5C5—C20—H20B110.9
H7A—C7—H7B109.5S5—C20—H20B110.9
C6—C7—H7C109.5H20A—C20—H20B108.9
H7A—C7—H7C109.5N3—C21—S5123.4 (2)
H7B—C7—H7C109.5N3—C21—S6130.8 (2)
C2—C8—H8A109.5S5—C21—S6105.75 (17)
C2—C8—H8B109.5N3—C22—C23113.0 (9)
H8A—C8—H8B109.5N3—C22—H22A109.0
C2—C8—H8C109.5C23—C22—H22A109.0
H8A—C8—H8C109.5N3—C22—H22B109.0
H8B—C8—H8C109.5C23—C22—H22B109.0
C4—C9—H9A109.5H22A—C22—H22B107.8
C4—C9—H9B109.5C24—C23—C22113.0 (14)
H9A—C9—H9B109.5C24—C23—H23A109.0
C4—C9—H9C109.5C22—C23—H23A109.0
H9A—C9—H9C109.5C24—C23—H23B109.0
H9B—C9—H9C109.5C22—C23—H23B109.0
C1—C10—S1108.9 (2)H23A—C23—H23B107.8
C1—C10—H10A109.9C23—C24—S6114.6 (7)
S1—C10—H10A109.9C23—C24—H24A108.6
C1—C10—H10B109.9S6—C24—H24A108.6
S1—C10—H10B109.9C23—C24—H24B108.6
H10A—C10—H10B108.3S6—C24—H24B108.6
N1—C11—S2130.7 (2)H24A—C24—H24B107.6
N1—C11—S1121.1 (2)N3—C22'—C23'115.0 (9)
S2—C11—S1108.22 (17)N3—C22'—H22C108.5
N1—C12—C13115.0 (3)C23'—C22'—H22C108.5
N1—C12—H12A108.5N3—C22'—H22D108.5
C13—C12—H12A108.5C23'—C22'—H22D108.5
N1—C12—H12B108.5H22C—C22'—H22D107.5
C13—C12—H12B108.5C24'—C23'—C22'109.9 (11)
H12A—C12—H12B107.5C24'—C23'—H23C109.7
C14—C13—C12113.1 (3)C22'—C23'—H23C109.7
C14—C13—H13A108.9C24'—C23'—H23D109.7
C12—C13—H13A108.9C22'—C23'—H23D109.7
C14—C13—H13B108.9H23C—C23'—H23D108.2
C12—C13—H13B108.9C23'—C24'—S6109.9 (6)
H13A—C13—H13B107.8C23'—C24'—H24C109.7
C13—C14—S2112.3 (2)S6—C24'—H24C109.7
C13—C14—H14A109.1C23'—C24'—H24D109.7
S2—C14—H14A109.1S6—C24'—H24D109.7
C13—C14—H14B109.1H24C—C24'—H24D108.2
C6—C1—C2—C3−1.7 (4)C2—C3—C15—S389.1 (3)
C10—C1—C2—C3174.9 (3)C16—S3—C15—C3166.1 (2)
C6—C1—C2—C8178.7 (3)C17—N2—C16—S3−179.5 (2)
C10—C1—C2—C8−4.7 (4)C17—N2—C16—S4−0.1 (5)
C1—C2—C3—C4−3.3 (4)C15—S3—C16—N26.4 (3)
C8—C2—C3—C4176.2 (3)C15—S3—C16—S4−173.11 (17)
C1—C2—C3—C15177.9 (3)C19—S4—C16—N27.6 (3)
C8—C2—C3—C15−2.5 (4)C19—S4—C16—S3−172.93 (16)
C2—C3—C4—C55.5 (4)C16—N2—C17—C18−36.0 (4)
C15—C3—C4—C5−175.7 (3)N2—C17—C18—C1965.7 (3)
C2—C3—C4—C9−173.6 (3)C17—C18—C19—S4−54.5 (3)
C15—C3—C4—C95.2 (4)C16—S4—C19—C1820.3 (3)
C3—C4—C5—C6−2.6 (4)C4—C5—C20—S591.8 (3)
C9—C4—C5—C6176.5 (3)C6—C5—C20—S5−83.3 (3)
C3—C4—C5—C20−177.6 (3)C21—S5—C20—C5−158.9 (2)
C9—C4—C5—C201.5 (4)C22—N3—C21—S5−170.7 (8)
C4—C5—C6—C1−2.4 (4)C22'—N3—C21—S5172.5 (6)
C20—C5—C6—C1172.6 (3)C22—N3—C21—S611.8 (9)
C4—C5—C6—C7179.1 (3)C22'—N3—C21—S6−5.0 (7)
C20—C5—C6—C7−5.9 (4)C20—S5—C21—N3−5.3 (3)
C2—C1—C6—C54.6 (4)C20—S5—C21—S6172.78 (16)
C10—C1—C6—C5−172.1 (3)C24—S6—C21—N3−17.4 (5)
C2—C1—C6—C7−176.9 (3)C24'—S6—C21—N32.0 (5)
C10—C1—C6—C76.4 (4)C24—S6—C21—S5164.7 (4)
C2—C1—C10—S191.8 (3)C24'—S6—C21—S5−175.9 (4)
C6—C1—C10—S1−91.5 (3)C21—N3—C22—C23−25.6 (18)
C11—S1—C10—C1175.1 (2)C22'—N3—C22—C2342 (3)
C12—N1—C11—S2−1.0 (5)N3—C22—C23—C2451 (2)
C12—N1—C11—S1178.6 (3)C22—C23—C24—S6−62.3 (19)
C14—S2—C11—N14.1 (4)C21—S6—C24—C2340.2 (12)
C14—S2—C11—S1−175.66 (17)C24'—S6—C24—C23−68.8 (15)
C10—S1—C11—N111.6 (3)C21—N3—C22'—C23'36.9 (13)
C10—S1—C11—S2−168.71 (17)C22—N3—C22'—C23'−84 (4)
C11—N1—C12—C13−30.1 (5)N3—C22'—C23'—C24'−68.7 (16)
N1—C12—C13—C1460.7 (5)C22'—C23'—C24'—S661.7 (13)
C12—C13—C14—S2−55.0 (4)C21—S6—C24'—C23'−29.7 (11)
C11—S2—C14—C1324.1 (3)C24—S6—C24'—C23'44.4 (12)
C4—C3—C15—S3−89.7 (3)
Table 1
Selected geometric parameters (Å, °) top
S1—C111.772 (3)S3—C151.828 (3)
S1—C101.824 (3)S5—C211.759 (3)
S3—C161.768 (3)S5—C201.822 (3)
N1—C11—S2130.7 (2)S3—C16—S4108.78 (16)
S2—C11—S1108.22 (17)N3—C21—S6130.8 (2)
N2—C16—S4129.7 (2)S5—C21—S6105.75 (17)
Acknowledgements top

We gratefully acknowledge the 05 L003 project supported by the Education Department of Liao Ning Province in China.

references
References top

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