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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029157/bv2058sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029157/bv2058Isup2.hkl
Contains datablock I

CCDC reference: 657661

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.055
  • wR factor = 0.139
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B ABSMU01_ALERT_1_B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.538 Value of mu given = 0.584 PLAT051_ALERT_1_B Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 7.88 Perc.
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 12.03 Cell volume su given = 9.00 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.81 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT213_ALERT_2_C Atom C24' has ADP max/min Ratio ............. 4.00 oblat PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT412_ALERT_2_C Short Intra XH3 .. XHn H8B .. H15A .. 1.88 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 20.10 Deg. C24 -S6 -C24' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 16.30 Deg. C22 -N3 -C22' 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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)].

Structure description 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).

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

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 m3
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 mm1
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)
Confocal monochromatorRint = 0.043
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 1.4°
ω scansh = 2120
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1212
Tmin = 0.900, Tmax = 0.989l = 1321
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 Å3
7 restraintsΔρmin = 0.42 e Å3
Crystal data top
C24H33N3S6V = 2637.6 (9) Å3
Mr = 555.89Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.146 (3) ŵ = 0.58 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0557 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.08Δρmax = 1.17 e Å3
5178 reflectionsΔρmin = 0.42 e Å3
329 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*/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)
S60.01276 (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)
N30.09428 (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*
H20B0.01740.53150.79000.036*
C210.0352 (2)0.4136 (3)0.61307 (19)0.0249 (6)
C220.1721 (8)0.5025 (18)0.4950 (7)0.029 (3)0.462 (15)
H22A0.18770.59510.47520.035*0.462 (15)
H22B0.22380.46230.49680.035*0.462 (15)
C230.1552 (8)0.4282 (10)0.4290 (6)0.038 (3)0.462 (15)
H23A0.21190.42180.37270.046*0.462 (15)
H23B0.11230.47890.41790.046*0.462 (15)
C240.1187 (7)0.2907 (10)0.4594 (6)0.048 (3)0.462 (15)
H24A0.11340.24600.41160.058*0.462 (15)
H24B0.16220.24020.46960.058*0.462 (15)
C22'0.1523 (9)0.5088 (14)0.4878 (7)0.035 (3)0.538 (15)
H22C0.12160.56280.46310.042*0.538 (15)
H22D0.20820.55520.47490.042*0.538 (15)
C23'0.1763 (5)0.3763 (11)0.4411 (6)0.037 (2)0.538 (15)
H23C0.20090.31730.46940.045*0.538 (15)
H23D0.22260.38870.37890.045*0.538 (15)
C24'0.0947 (6)0.3143 (11)0.4453 (4)0.039 (2)0.538 (15)
H24C0.06990.37360.41730.046*0.538 (15)
H24D0.11110.22970.41260.046*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, º) 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—C31.7 (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—S3179.5 (2)
C10—C1—C2—C84.7 (4)C17—N2—C16—S40.1 (5)
C1—C2—C3—C43.3 (4)C15—S3—C16—N26.4 (3)
C8—C2—C3—C4176.2 (3)C15—S3—C16—S4173.11 (17)
C1—C2—C3—C15177.9 (3)C19—S4—C16—N27.6 (3)
C8—C2—C3—C152.5 (4)C19—S4—C16—S3172.93 (16)
C2—C3—C4—C55.5 (4)C16—N2—C17—C1836.0 (4)
C15—C3—C4—C5175.7 (3)N2—C17—C18—C1965.7 (3)
C2—C3—C4—C9173.6 (3)C17—C18—C19—S454.5 (3)
C15—C3—C4—C95.2 (4)C16—S4—C19—C1820.3 (3)
C3—C4—C5—C62.6 (4)C4—C5—C20—S591.8 (3)
C9—C4—C5—C6176.5 (3)C6—C5—C20—S583.3 (3)
C3—C4—C5—C20177.6 (3)C21—S5—C20—C5158.9 (2)
C9—C4—C5—C201.5 (4)C22—N3—C21—S5170.7 (8)
C4—C5—C6—C12.4 (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—S65.0 (7)
C20—C5—C6—C75.9 (4)C20—S5—C21—N35.3 (3)
C2—C1—C6—C54.6 (4)C20—S5—C21—S6172.78 (16)
C10—C1—C6—C5172.1 (3)C24—S6—C21—N317.4 (5)
C2—C1—C6—C7176.9 (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—S5175.9 (4)
C6—C1—C10—S191.5 (3)C21—N3—C22—C2325.6 (18)
C11—S1—C10—C1175.1 (2)C22'—N3—C22—C2342 (3)
C12—N1—C11—S21.0 (5)N3—C22—C23—C2451 (2)
C12—N1—C11—S1178.6 (3)C22—C23—C24—S662.3 (19)
C14—S2—C11—N14.1 (4)C21—S6—C24—C2340.2 (12)
C14—S2—C11—S1175.66 (17)C24'—S6—C24—C2368.8 (15)
C10—S1—C11—N111.6 (3)C21—N3—C22'—C23'36.9 (13)
C10—S1—C11—S2168.71 (17)C22—N3—C22'—C23'84 (4)
C11—N1—C12—C1330.1 (5)N3—C22'—C23'—C24'68.7 (16)
N1—C12—C13—C1460.7 (5)C22'—C23'—C24'—S661.7 (13)
C12—C13—C14—S255.0 (4)C21—S6—C24'—C23'29.7 (11)
C11—S2—C14—C1324.1 (3)C24—S6—C24'—C23'44.4 (12)
C4—C3—C15—S389.7 (3)

Experimental details

Crystal data
Chemical formulaC24H33N3S6
Mr555.89
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)17.146 (3), 10.123 (2), 17.408 (4)
β (°) 119.20 (3)
V3)2637.6 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.58
Crystal size (mm)0.20 × 0.18 × 0.02
Data collection
DiffractometerRigaku Saturn
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.900, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
17102, 5178, 4350
Rint0.043
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.139, 1.08
No. of reflections5178
No. of parameters329
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.17, 0.42

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 1999), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) 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)
 

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