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Two mol­ecules make up the asymmetric unit of the chiral title compound, C17H26N4O2S2. The dihedral angles between the imidazole­thione rings are 23.7 (5) and 31.4 (5)° in the two mol­ecules. The packing appears to be consolidated by pseudo-aromatic stacking inter­actions involving the imidazole­thione rings [centroid-to-centroid separations = 3.669 (8) and 3.675 (8) Å]. Short C—H...S and C—H...O contacts are also apparent in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680706148X/sj2406sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680706148X/sj2406Isup2.hkl
Contains datablock I

CCDC reference: 673067

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.097
  • wR factor = 0.241
  • Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 12
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.131 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.13 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT213_ALERT_2_C Atom C29 has ADP max/min Ratio ............. 3.30 prola PLAT230_ALERT_2_C Hirshfeld Test Diff for S4 - C29 .. 6.28 su PLAT413_ALERT_2_C Short Inter XH3 .. XHn H17C .. H26B .. 2.12 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.71 From the CIF: _reflns_number_total 8499 Count of symmetry unique reflns 4782 Completeness (_total/calc) 177.73% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3717 Fraction of Friedel pairs measured 0.777 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23 ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24 ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of our ongoing investigations of chiral, C2-symmetric catalysts (Marshall & Harrison, 2007), the title compound, (I), which is an intermediate in such materials, has been synthesized and structurally characterized.

There are two molecules of (I) in the asymmetric unit (Fig. 1). All the chiral centres (C6, C7, C23, C24) possess their expected R configuarations. The dihedral angle between the N1/N2/C1/C2/C3 (IM1) and N3/N4/C10/C11/C12 (IM2) imidazole rings is 23.7 (5)°; that between the N5/N6/C18/C19/C20 (IM3) and N7/N8/C27/C28/C29 (IM4) planes is 31.4 (5)°. The thio-imidazole rings show their expected geometries (Marshall & Harrison, 2007; Williamson et al., 2006) and indeed all the geometrical parameters of the two molecules may be regarded as normal (Allen et al., 1987).

The crystal packing for (I) features short face-to-face contacts between the imidazole rings with a centroid-centroid separation of 3.675 (8) Å for IM1···IM2i (i = 2 - x, 1/2 + y, 1 - z) and 3.669 (8) Å for IM3···IM4ii (ii = 1 - x, -1/2 + y, -z). Such contacts are usually referred to as aromatic ππ stacking. However, the aromatic nature of the thio-imidazole ring is questionable (Williamson et al., 2006). If these really represent attractive intermolecular forces in the crystal, then [010] chains of molecules arise (Fig. 2). Some short C—H···S and C—H···O contacts (Table 1) also occur in the crystal.

Related literature top

For background, see: Marshall & Harrison (2007); Williamson et al. (2006). For reference structural data, see: Allen et al. (1987).

Experimental top

A mixture of (4R,5R)-4,5-bis(1-methylimidazolium-3-ethyl)-2,2-dimethly-1,3-dioxolane dibromide (0.46 g, 0.96 mmol), methanol (10 ml), pyridine (0.5 ml), sulfur (0.09 g, 2.89 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.64 g, 4.23 mmol) was heated at 338 K for 18 h. Once cooled to room temperature the mixture was opened to water (40 ml) and extracted with chloroform (3 × 20 ml). The combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to leave a brown residue. The crude product was purified by column chromatography (SiO2, ethyl acetate: petroleum ether v/v 1:1, loaded as a dichloromethane solution) to give the title compound (0.34 g, 93%) as a colourless solid which was recrystallized from diethyl ether, acetone (v/v 1:1) to give colourless blades of (I); mp 390 K.

Refinement top

The small crystal used for data collection was a weak scatterer, which may correlate with the rather high residuals.

The H atoms were placed in calculated positions (C—H = 0.95–1.00 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate, but not to tip, to best fit the electron density.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997), HKL SCALEPACK (Otwinowski & Minor 1997) and SORTAV (Blessing 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids. All the H atoms are omitted for clarity except those attached to the chiral C atoms, which are represented as arbitrary spheres.
[Figure 2] Fig. 2. Part of a chain of C1-containing molecules in the crystal of (I), with the dashed lines indicating the pseudo-aromatic stacking contacts between the centroids of the 5-membered rings (see text). All H atoms omitted for clarity. Symmetry codes: (i) 2 - x, 1/2 + y, 1 - z; (ii) 2 - x, 1/2 + y, 1 - z. The C18-containing molecule forms similar chains.
(4R,5R)-2,2-Dimethyl-4,5-bis[2-(3-methyl-2-thioxo-2,3-dihydro-1H- imidazol-2-yl)ethyl]-1,3-dioxolane top
Crystal data top
C17H26N4O2S2F(000) = 816
Mr = 382.54Dx = 1.278 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 10746 reflections
a = 6.827 (5) Åθ = 2.9–27.5°
b = 20.732 (9) ŵ = 0.29 mm1
c = 14.071 (8) ÅT = 120 K
β = 93.68 (2)°Blade, colourless
V = 1988 (4) Å30.15 × 0.07 × 0.03 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
4275 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.131
Graphite monochromatorθmax = 27.7°, θmin = 3.0°
ω and ϕ scansh = 88
21365 measured reflectionsk = 2626
8499 independent reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.097H-atom parameters constrained
wR(F2) = 0.241 w = 1/[σ2(Fo2) + (0.1095P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
8499 reflectionsΔρmax = 1.19 e Å3
458 parametersΔρmin = 0.38 e Å3
1 restraintAbsolute structure: Flack (1983), with 3717 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (14)
Crystal data top
C17H26N4O2S2V = 1988 (4) Å3
Mr = 382.54Z = 4
Monoclinic, P21Mo Kα radiation
a = 6.827 (5) ŵ = 0.29 mm1
b = 20.732 (9) ÅT = 120 K
c = 14.071 (8) Å0.15 × 0.07 × 0.03 mm
β = 93.68 (2)°
Data collection top
Nonius KappaCCD
diffractometer
4275 reflections with I > 2σ(I)
21365 measured reflectionsRint = 0.131
8499 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.097H-atom parameters constrained
wR(F2) = 0.241Δρmax = 1.19 e Å3
S = 1.01Δρmin = 0.38 e Å3
8499 reflectionsAbsolute structure: Flack (1983), with 3717 Friedel pairs
458 parametersAbsolute structure parameter: 0.03 (14)
1 restraint
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
S11.0766 (3)0.09444 (11)0.37993 (15)0.0358 (6)
S21.1011 (3)0.25588 (10)0.38446 (15)0.0379 (6)
O10.9082 (7)0.0267 (2)0.7294 (3)0.0281 (13)
O20.9200 (8)0.1377 (2)0.7253 (4)0.0319 (14)
N10.6913 (9)0.0893 (3)0.4156 (4)0.0287 (15)
N20.8869 (8)0.0746 (3)0.5447 (4)0.0225 (15)
N31.3291 (10)0.2429 (3)0.5522 (4)0.0322 (16)
N41.4920 (9)0.2678 (3)0.4321 (4)0.0313 (16)
C10.8820 (11)0.0868 (4)0.4470 (6)0.0286 (19)
C20.5784 (11)0.0793 (4)0.4942 (6)0.0283 (19)
H20.43910.07880.49160.034*
C30.6915 (12)0.0707 (4)0.5710 (6)0.034 (2)
H30.65020.06330.63330.041*
C41.0701 (12)0.0718 (4)0.6069 (6)0.033 (2)
H4A1.17180.09870.57900.039*
H4B1.04550.08980.67020.039*
C51.1441 (12)0.0030 (4)0.6182 (6)0.034 (2)
H5A1.25250.00240.66840.041*
H5B1.19930.01040.55790.041*
C60.9947 (13)0.0455 (4)0.6431 (5)0.034 (2)
H60.89020.04860.59010.041*
C71.0671 (13)0.1117 (4)0.6699 (6)0.035 (2)
H71.19400.10860.70930.042*
C81.0929 (14)0.1560 (4)0.5824 (6)0.039 (2)
H8A1.18660.13540.54100.046*
H8B0.96520.15970.54540.046*
C91.1676 (12)0.2245 (4)0.6086 (6)0.033 (2)
H9A1.05890.25580.59770.039*
H9B1.21140.22590.67700.039*
C101.5189 (14)0.2460 (4)0.5853 (6)0.039 (2)
H101.56970.23780.64860.046*
C111.6230 (11)0.2632 (4)0.5099 (6)0.037 (2)
H111.76040.27070.51100.044*
C121.3064 (11)0.2562 (4)0.4560 (6)0.0285 (19)
C130.8483 (12)0.0842 (4)0.7781 (5)0.034 (2)
C140.9443 (16)0.0811 (5)0.8777 (6)0.056 (3)
H14A0.91870.12130.91140.084*
H14B1.08620.07540.87450.084*
H14C0.89030.04470.91190.084*
C150.6255 (13)0.0889 (4)0.7705 (7)0.050 (3)
H15A0.58430.12650.80640.076*
H15B0.56940.04970.79660.076*
H15C0.57920.09350.70340.076*
C160.6178 (12)0.1033 (4)0.3189 (6)0.039 (2)
H16A0.48580.12180.31950.058*
H16B0.70540.13410.29030.058*
H16C0.61260.06330.28150.058*
C171.5424 (12)0.2842 (4)0.3361 (6)0.039 (2)
H17A1.68420.29130.33560.058*
H17B1.47270.32350.31520.058*
H17C1.50420.24870.29270.058*
S30.3242 (3)0.08682 (10)0.11152 (15)0.0346 (5)
S40.4476 (3)0.27361 (10)0.13945 (14)0.0315 (5)
O30.6325 (8)0.0390 (2)0.2112 (4)0.0354 (14)
O40.6722 (7)0.1490 (2)0.2102 (4)0.0318 (14)
N50.0519 (9)0.0961 (3)0.0621 (4)0.0286 (16)
N60.1467 (9)0.0640 (3)0.0544 (5)0.0290 (16)
N70.6796 (9)0.2483 (3)0.0229 (4)0.0239 (15)
N80.8460 (9)0.2680 (3)0.1002 (4)0.0284 (15)
C180.1379 (11)0.0834 (4)0.0398 (5)0.0272 (18)
C190.1644 (12)0.0857 (4)0.0162 (6)0.037 (2)
H190.30200.09160.01840.044*
C200.0388 (11)0.0657 (4)0.0878 (6)0.030 (2)
H200.07200.05470.15040.036*
C210.3238 (12)0.0426 (4)0.1091 (6)0.034 (2)
H21A0.42640.07620.10540.041*
H21B0.29450.03810.17680.041*
C220.4043 (12)0.0216 (4)0.0743 (6)0.034 (2)
H22A0.51630.01290.03490.041*
H22B0.30090.04340.03340.041*
C230.4715 (11)0.0666 (4)0.1552 (5)0.0289 (19)
H230.36030.07580.19610.035*
C240.5638 (12)0.1292 (3)0.1247 (5)0.0260 (19)
H240.65490.12090.07320.031*
C250.4178 (11)0.1814 (4)0.0942 (5)0.0258 (18)
H25A0.31750.18470.14180.031*
H25B0.35010.16920.03250.031*
C260.5161 (11)0.2471 (4)0.0840 (6)0.0288 (19)
H26A0.41580.27820.05870.035*
H26B0.56350.26220.14820.035*
C270.8729 (13)0.2427 (4)0.0525 (6)0.036 (2)
H270.92490.23260.11500.044*
C280.9747 (11)0.2542 (4)0.0237 (6)0.0288 (19)
H281.11360.25300.02480.035*
C290.6561 (11)0.2632 (4)0.0717 (5)0.0283 (19)
C300.7339 (12)0.0893 (4)0.2601 (6)0.037 (2)
C310.9550 (12)0.0815 (5)0.2540 (7)0.055 (3)
H31A1.02300.11750.28720.082*
H31B0.98660.08140.18710.082*
H31C0.99740.04080.28400.082*
C320.6749 (17)0.0963 (5)0.3611 (6)0.060 (3)
H32A0.75040.13120.39270.090*
H32B0.70140.05580.39570.090*
H32C0.53450.10620.36060.090*
C330.1337 (12)0.1177 (4)0.1555 (6)0.039 (2)
H33A0.26120.13820.14850.058*
H33B0.04400.14870.18230.058*
H33C0.15070.08050.19820.058*
C340.8937 (12)0.2850 (4)0.1942 (6)0.035 (2)
H34A1.02320.30550.19170.053*
H34B0.79500.31510.22190.053*
H34C0.89560.24610.23360.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0335 (13)0.0382 (13)0.0357 (12)0.0003 (11)0.0030 (10)0.0042 (10)
S20.0347 (13)0.0385 (14)0.0395 (13)0.0065 (10)0.0047 (10)0.0006 (10)
O10.034 (3)0.018 (3)0.033 (3)0.004 (2)0.010 (3)0.000 (2)
O20.032 (3)0.024 (3)0.042 (3)0.002 (2)0.014 (3)0.007 (3)
N10.040 (4)0.010 (3)0.035 (4)0.007 (3)0.004 (3)0.005 (3)
N20.018 (3)0.023 (4)0.027 (3)0.009 (3)0.006 (3)0.001 (3)
N30.039 (4)0.023 (4)0.034 (4)0.000 (3)0.005 (4)0.004 (3)
N40.030 (4)0.033 (4)0.033 (4)0.001 (3)0.013 (3)0.001 (3)
C10.023 (4)0.010 (4)0.051 (5)0.003 (3)0.012 (4)0.007 (4)
C20.017 (4)0.027 (5)0.041 (5)0.000 (4)0.002 (4)0.002 (4)
C30.038 (5)0.029 (5)0.037 (5)0.002 (4)0.021 (4)0.004 (4)
C40.038 (5)0.024 (5)0.035 (5)0.010 (4)0.007 (4)0.004 (4)
C50.039 (5)0.035 (5)0.029 (5)0.002 (4)0.001 (4)0.009 (4)
C60.052 (6)0.030 (5)0.021 (4)0.008 (4)0.000 (4)0.007 (4)
C70.052 (6)0.023 (5)0.031 (5)0.005 (4)0.006 (4)0.002 (4)
C80.048 (6)0.036 (5)0.031 (5)0.015 (4)0.003 (4)0.009 (4)
C90.036 (5)0.032 (5)0.031 (5)0.005 (4)0.004 (4)0.007 (4)
C100.064 (7)0.022 (5)0.028 (5)0.012 (4)0.011 (5)0.000 (4)
C110.018 (4)0.040 (6)0.052 (6)0.010 (4)0.003 (4)0.005 (5)
C120.025 (4)0.020 (4)0.043 (5)0.001 (4)0.019 (4)0.003 (4)
C130.046 (5)0.023 (5)0.036 (5)0.003 (4)0.016 (4)0.000 (4)
C140.096 (8)0.039 (6)0.035 (5)0.009 (6)0.018 (5)0.000 (5)
C150.042 (6)0.021 (5)0.090 (7)0.001 (4)0.023 (5)0.002 (5)
C160.029 (5)0.044 (6)0.044 (5)0.008 (4)0.007 (4)0.011 (4)
C170.031 (5)0.040 (6)0.046 (5)0.012 (4)0.008 (4)0.010 (4)
S30.0304 (12)0.0326 (12)0.0412 (12)0.0007 (10)0.0048 (9)0.0001 (10)
S40.0220 (11)0.0397 (13)0.0323 (11)0.0040 (10)0.0029 (9)0.0048 (10)
O30.042 (3)0.014 (3)0.048 (4)0.001 (2)0.015 (3)0.001 (3)
O40.029 (3)0.026 (3)0.038 (3)0.003 (2)0.015 (3)0.001 (2)
N50.034 (4)0.017 (4)0.033 (4)0.002 (3)0.006 (3)0.003 (3)
N60.029 (4)0.023 (4)0.034 (4)0.001 (3)0.006 (3)0.006 (3)
N70.021 (4)0.029 (4)0.021 (3)0.002 (3)0.002 (3)0.004 (3)
N80.028 (4)0.019 (4)0.038 (4)0.005 (3)0.003 (3)0.003 (3)
C180.038 (5)0.015 (4)0.028 (4)0.009 (4)0.002 (4)0.006 (4)
C190.033 (5)0.028 (5)0.049 (5)0.007 (4)0.001 (4)0.005 (4)
C200.021 (5)0.030 (5)0.040 (5)0.004 (4)0.009 (4)0.003 (4)
C210.038 (5)0.025 (5)0.037 (5)0.002 (4)0.005 (4)0.007 (4)
C220.037 (5)0.023 (5)0.042 (5)0.012 (4)0.002 (4)0.001 (4)
C230.026 (5)0.025 (5)0.035 (5)0.003 (3)0.005 (4)0.002 (4)
C240.034 (5)0.024 (5)0.021 (4)0.010 (4)0.007 (4)0.005 (3)
C250.026 (4)0.026 (5)0.024 (4)0.000 (3)0.010 (3)0.003 (3)
C260.028 (5)0.020 (4)0.039 (5)0.000 (3)0.005 (4)0.002 (4)
C270.057 (6)0.019 (5)0.031 (5)0.011 (4)0.013 (4)0.004 (4)
C280.020 (4)0.022 (4)0.045 (5)0.004 (4)0.001 (4)0.008 (4)
C290.029 (5)0.017 (4)0.041 (5)0.016 (4)0.017 (4)0.015 (4)
C300.041 (5)0.027 (5)0.039 (5)0.001 (4)0.023 (4)0.007 (4)
C310.045 (6)0.029 (5)0.086 (7)0.016 (5)0.025 (5)0.000 (6)
C320.102 (9)0.035 (6)0.041 (6)0.014 (5)0.012 (6)0.007 (4)
C330.035 (5)0.030 (5)0.050 (6)0.011 (4)0.002 (4)0.005 (4)
C340.041 (5)0.027 (5)0.040 (5)0.013 (4)0.018 (4)0.004 (4)
Geometric parameters (Å, º) top
S1—C11.685 (9)S3—C181.675 (8)
S2—C121.672 (9)S4—C291.675 (9)
O1—C61.437 (9)O3—C301.406 (9)
O1—C131.447 (9)O3—C231.430 (9)
O2—C71.417 (10)O4—C241.431 (9)
O2—C131.439 (9)O4—C301.471 (9)
N1—C11.349 (9)N5—C181.339 (9)
N1—C21.403 (10)N5—C191.400 (10)
N1—C161.449 (10)N5—C331.465 (10)
N2—C11.397 (9)N6—C201.379 (10)
N2—C31.409 (10)N6—C181.383 (9)
N2—C41.480 (9)N6—C211.460 (9)
N3—C101.350 (11)N7—C271.363 (10)
N3—C121.381 (9)N7—C291.366 (9)
N3—C91.450 (10)N7—C261.452 (9)
N4—C121.353 (9)N8—C281.375 (9)
N4—C111.372 (10)N8—C291.386 (9)
N4—C171.456 (10)N8—C341.426 (10)
C2—C31.299 (10)C19—C201.346 (10)
C2—H20.9500C19—H190.9500
C3—H30.9500C20—H200.9500
C4—C51.518 (11)C21—C221.533 (10)
C4—H4A0.9900C21—H21A0.9900
C4—H4B0.9900C21—H21B0.9900
C5—C61.490 (11)C22—C231.520 (10)
C5—H5A0.9900C22—H22A0.9900
C5—H5B0.9900C22—H22B0.9900
C6—C71.500 (11)C23—C241.517 (11)
C6—H61.0000C23—H231.0000
C7—C81.554 (11)C24—C251.515 (10)
C7—H71.0000C24—H241.0000
C8—C91.546 (11)C25—C261.529 (11)
C8—H8A0.9900C25—H25A0.9900
C8—H8B0.9900C25—H25B0.9900
C9—H9A0.9900C26—H26A0.9900
C9—H9B0.9900C26—H26B0.9900
C10—C111.362 (11)C27—C281.336 (11)
C10—H100.9500C27—H270.9500
C11—H110.9500C28—H280.9500
C13—C141.511 (11)C30—C321.510 (12)
C13—C151.521 (11)C30—C311.526 (12)
C14—H14A0.9800C31—H31A0.9800
C14—H14B0.9800C31—H31B0.9800
C14—H14C0.9800C31—H31C0.9800
C15—H15A0.9800C32—H32A0.9800
C15—H15B0.9800C32—H32B0.9800
C15—H15C0.9800C32—H32C0.9800
C16—H16A0.9800C33—H33A0.9800
C16—H16B0.9800C33—H33B0.9800
C16—H16C0.9800C33—H33C0.9800
C17—H17A0.9800C34—H34A0.9800
C17—H17B0.9800C34—H34B0.9800
C17—H17C0.9800C34—H34C0.9800
C6—O1—C13108.7 (5)C30—O3—C23108.0 (5)
C7—O2—C13105.5 (6)C24—O4—C30106.1 (5)
C1—N1—C2107.7 (6)C18—N5—C19110.9 (6)
C1—N1—C16125.7 (7)C18—N5—C33125.3 (7)
C2—N1—C16126.5 (6)C19—N5—C33123.8 (7)
C1—N2—C3107.8 (6)C20—N6—C18109.6 (6)
C1—N2—C4123.7 (6)C20—N6—C21125.1 (7)
C3—N2—C4128.4 (6)C18—N6—C21125.3 (7)
C10—N3—C12111.9 (7)C27—N7—C29111.6 (6)
C10—N3—C9124.8 (7)C27—N7—C26125.7 (6)
C12—N3—C9123.2 (7)C29—N7—C26122.3 (6)
C12—N4—C11111.3 (6)C28—N8—C29108.7 (6)
C12—N4—C17123.5 (7)C28—N8—C34127.2 (6)
C11—N4—C17125.2 (6)C29—N8—C34124.1 (6)
N1—C1—N2106.9 (7)N5—C18—N6105.3 (6)
N1—C1—S1126.3 (6)N5—C18—S3127.7 (6)
N2—C1—S1126.8 (5)N6—C18—S3127.0 (6)
C3—C2—N1110.4 (7)C20—C19—N5106.3 (7)
C3—C2—H2124.8C20—C19—H19126.8
N1—C2—H2124.8N5—C19—H19126.8
C2—C3—N2107.2 (7)C19—C20—N6107.9 (7)
C2—C3—H3126.4C19—C20—H20126.1
N2—C3—H3126.4N6—C20—H20126.1
N2—C4—C5111.2 (6)N6—C21—C22113.3 (6)
N2—C4—H4A109.4N6—C21—H21A108.9
C5—C4—H4A109.4C22—C21—H21A108.9
N2—C4—H4B109.4N6—C21—H21B108.9
C5—C4—H4B109.4C22—C21—H21B108.9
H4A—C4—H4B108.0H21A—C21—H21B107.7
C6—C5—C4115.5 (7)C23—C22—C21113.0 (7)
C6—C5—H5A108.4C23—C22—H22A109.0
C4—C5—H5A108.4C21—C22—H22A109.0
C6—C5—H5B108.4C23—C22—H22B109.0
C4—C5—H5B108.4C21—C22—H22B109.0
H5A—C5—H5B107.5H22A—C22—H22B107.8
O1—C6—C5109.8 (7)O3—C23—C24100.4 (6)
O1—C6—C7100.6 (6)O3—C23—C22110.6 (6)
C5—C6—C7117.2 (7)C24—C23—C22115.1 (7)
O1—C6—H6109.6O3—C23—H23110.1
C5—C6—H6109.6C24—C23—H23110.1
C7—C6—H6109.6C22—C23—H23110.1
O2—C7—C6104.6 (7)O4—C24—C25109.2 (6)
O2—C7—C8109.4 (7)O4—C24—C23102.1 (6)
C6—C7—C8113.2 (7)C25—C24—C23114.5 (7)
O2—C7—H7109.8O4—C24—H24110.3
C6—C7—H7109.8C25—C24—H24110.3
C8—C7—H7109.8C23—C24—H24110.3
C9—C8—C7114.0 (7)C24—C25—C26112.2 (6)
C9—C8—H8A108.8C24—C25—H25A109.2
C7—C8—H8A108.8C26—C25—H25A109.2
C9—C8—H8B108.8C24—C25—H25B109.2
C7—C8—H8B108.8C26—C25—H25B109.2
H8A—C8—H8B107.6H25A—C25—H25B107.9
N3—C9—C8111.2 (6)N7—C26—C25115.4 (6)
N3—C9—H9A109.4N7—C26—H26A108.4
C8—C9—H9A109.4C25—C26—H26A108.4
N3—C9—H9B109.4N7—C26—H26B108.4
C8—C9—H9B109.4C25—C26—H26B108.4
H9A—C9—H9B108.0H26A—C26—H26B107.5
N3—C10—C11106.3 (7)C28—C27—N7106.4 (7)
N3—C10—H10126.8C28—C27—H27126.8
C11—C10—H10126.8N7—C27—H27126.8
C10—C11—N4107.1 (7)C27—C28—N8109.1 (7)
C10—C11—H11126.5C27—C28—H28125.5
N4—C11—H11126.5N8—C28—H28125.5
N4—C12—N3103.3 (7)N7—C29—N8104.2 (6)
N4—C12—S2127.9 (6)N7—C29—S4128.8 (6)
N3—C12—S2128.8 (6)N8—C29—S4127.0 (6)
O2—C13—O1106.0 (6)O3—C30—O4105.9 (5)
O2—C13—C14111.7 (7)O3—C30—C32112.3 (7)
O1—C13—C14106.6 (7)O4—C30—C32106.5 (7)
O2—C13—C15106.6 (7)O3—C30—C31110.6 (7)
O1—C13—C15109.4 (6)O4—C30—C31108.4 (7)
C14—C13—C15116.1 (8)C32—C30—C31112.8 (7)
C13—C14—H14A109.5C30—C31—H31A109.5
C13—C14—H14B109.5C30—C31—H31B109.5
H14A—C14—H14B109.5H31A—C31—H31B109.5
C13—C14—H14C109.5C30—C31—H31C109.5
H14A—C14—H14C109.5H31A—C31—H31C109.5
H14B—C14—H14C109.5H31B—C31—H31C109.5
C13—C15—H15A109.5C30—C32—H32A109.5
C13—C15—H15B109.5C30—C32—H32B109.5
H15A—C15—H15B109.5H32A—C32—H32B109.5
C13—C15—H15C109.5C30—C32—H32C109.5
H15A—C15—H15C109.5H32A—C32—H32C109.5
H15B—C15—H15C109.5H32B—C32—H32C109.5
N1—C16—H16A109.5N5—C33—H33A109.5
N1—C16—H16B109.5N5—C33—H33B109.5
H16A—C16—H16B109.5H33A—C33—H33B109.5
N1—C16—H16C109.5N5—C33—H33C109.5
H16A—C16—H16C109.5H33A—C33—H33C109.5
H16B—C16—H16C109.5H33B—C33—H33C109.5
N4—C17—H17A109.5N8—C34—H34A109.5
N4—C17—H17B109.5N8—C34—H34B109.5
H17A—C17—H17B109.5H34A—C34—H34B109.5
N4—C17—H17C109.5N8—C34—H34C109.5
H17A—C17—H17C109.5H34A—C34—H34C109.5
H17B—C17—H17C109.5H34B—C34—H34C109.5
C2—N1—C1—N20.6 (8)C19—N5—C18—N60.5 (8)
C16—N1—C1—N2177.6 (7)C33—N5—C18—N6179.2 (7)
C2—N1—C1—S1178.7 (6)C19—N5—C18—S3178.0 (6)
C16—N1—C1—S14.3 (11)C33—N5—C18—S31.7 (11)
C3—N2—C1—N10.8 (8)C20—N6—C18—N50.4 (8)
C4—N2—C1—N1176.6 (6)C21—N6—C18—N5177.5 (6)
C3—N2—C1—S1178.9 (6)C20—N6—C18—S3177.9 (6)
C4—N2—C1—S15.4 (10)C21—N6—C18—S30.0 (11)
C1—N1—C2—C30.2 (9)C18—N5—C19—C200.4 (9)
C16—N1—C2—C3177.1 (7)C33—N5—C19—C20179.3 (7)
N1—C2—C3—N20.3 (9)N5—C19—C20—N60.1 (9)
C1—N2—C3—C20.7 (8)C18—N6—C20—C190.2 (9)
C4—N2—C3—C2176.2 (7)C21—N6—C20—C19177.8 (7)
C1—N2—C4—C594.4 (8)C20—N6—C21—C22110.2 (8)
C3—N2—C4—C590.7 (9)C18—N6—C21—C2267.4 (10)
N2—C4—C5—C648.6 (9)N6—C21—C22—C23137.8 (7)
C13—O1—C6—C5150.7 (6)C30—O3—C23—C2436.5 (8)
C13—O1—C6—C726.5 (7)C30—O3—C23—C22158.5 (7)
C4—C5—C6—O156.9 (9)C21—C22—C23—O363.6 (9)
C4—C5—C6—C7170.7 (7)C21—C22—C23—C24176.5 (7)
C13—O2—C7—C635.2 (7)C30—O4—C24—C25153.0 (6)
C13—O2—C7—C8156.8 (6)C30—O4—C24—C2331.5 (7)
O1—C6—C7—O237.8 (7)O3—C23—C24—O441.2 (7)
C5—C6—C7—O2156.7 (7)C22—C23—C24—O4159.9 (6)
O1—C6—C7—C8156.8 (7)O3—C23—C24—C25159.1 (6)
C5—C6—C7—C884.3 (9)C22—C23—C24—C2582.2 (9)
O2—C7—C8—C963.8 (9)O4—C24—C25—C2654.5 (8)
C6—C7—C8—C9180.0 (7)C23—C24—C25—C26168.2 (6)
C10—N3—C9—C8106.2 (8)C27—N7—C26—C2595.3 (9)
C12—N3—C9—C870.3 (9)C29—N7—C26—C2592.9 (8)
C7—C8—C9—N3132.0 (8)C24—C25—C26—N753.4 (9)
C12—N3—C10—C111.5 (9)C29—N7—C27—C280.0 (9)
C9—N3—C10—C11178.4 (7)C26—N7—C27—C28172.5 (7)
N3—C10—C11—N42.1 (9)N7—C27—C28—N81.0 (9)
C12—N4—C11—C102.1 (9)C29—N8—C28—C271.7 (8)
C17—N4—C11—C10179.0 (8)C34—N8—C28—C27177.9 (7)
C11—N4—C12—N31.1 (8)C27—N7—C29—N81.1 (8)
C17—N4—C12—N3179.9 (7)C26—N7—C29—N8171.8 (6)
C11—N4—C12—S2179.4 (6)C27—N7—C29—S4178.9 (6)
C17—N4—C12—S21.6 (11)C26—N7—C29—S48.3 (11)
C10—N3—C12—N40.3 (8)C28—N8—C29—N71.7 (7)
C9—N3—C12—N4177.2 (7)C34—N8—C29—N7178.0 (7)
C10—N3—C12—S2178.0 (6)C28—N8—C29—S4178.3 (6)
C9—N3—C12—S21.1 (11)C34—N8—C29—S42.0 (11)
C7—O2—C13—O118.3 (7)C23—O3—C30—O417.9 (8)
C7—O2—C13—C1497.4 (8)C23—O3—C30—C3297.9 (8)
C7—O2—C13—C15134.8 (7)C23—O3—C30—C31135.1 (7)
C6—O1—C13—O26.3 (7)C24—O4—C30—O39.8 (8)
C6—O1—C13—C14125.4 (7)C24—O4—C30—C32129.5 (7)
C6—O1—C13—C15108.2 (7)C24—O4—C30—C31108.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···S1i0.952.863.703 (8)148
C16—H16C···O30.982.353.321 (10)171
C33—H33C···O1ii0.982.493.424 (10)160
C34—H34C···O2iii0.982.333.266 (10)160
Symmetry codes: (i) x1, y, z; (ii) x1, y, z1; (iii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC17H26N4O2S2
Mr382.54
Crystal system, space groupMonoclinic, P21
Temperature (K)120
a, b, c (Å)6.827 (5), 20.732 (9), 14.071 (8)
β (°) 93.68 (2)
V3)1988 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.29
Crystal size (mm)0.15 × 0.07 × 0.03
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21365, 8499, 4275
Rint0.131
(sin θ/λ)max1)0.654
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.097, 0.241, 1.01
No. of reflections8499
No. of parameters458
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.19, 0.38
Absolute structureFlack (1983), with 3717 Friedel pairs
Absolute structure parameter0.03 (14)

Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO (Otwinowski & Minor 1997), HKL SCALEPACK (Otwinowski & Minor 1997) and SORTAV (Blessing 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···S1i0.952.863.703 (8)148
C16—H16C···O30.982.353.321 (10)171
C33—H33C···O1ii0.982.493.424 (10)160
C34—H34C···O2iii0.982.333.266 (10)160
Symmetry codes: (i) x1, y, z; (ii) x1, y, z1; (iii) x, y, z1.
 

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