PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o58.
Published online 2007 December 6. doi:  10.1107/S1600536807055948
PMCID: PMC2915016

(4S,5S)-2,2-Dimethyl-4,5-bis­(3-methyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl­meth­yl)-1,3-dioxolane

Abstract

In the chiral title compound, C15H22N4O2S2, there are two mol­ecules in the asymmetric unit with distinctly different conformations, as quanti­fied by torsion angles. The dihedral angles between the thio­imidazole rings are 81.59 (5) and 67.04 (4)°. One mol­ecule exhibits local twofold rotation symmetry, while the other displays no local symmetry. Inter­molecular C—H(...)O and C—H(...)S inter­actions are observed.

Related literature

For background, see: Marshall et al. (2004 [triangle]); Williamson et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-00o58-scheme1.jpg

Experimental

Crystal data

  • C15H22N4O2S2
  • M r = 354.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00o58-efi1.jpg
  • a = 10.462 (2) Å
  • b = 8.6043 (17) Å
  • c = 20.249 (4) Å
  • β = 103.19 (3)°
  • V = 1774.7 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.31 mm−1
  • T = 123 (2) K
  • 0.18 × 0.16 × 0.16 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: none
  • 13494 measured reflections
  • 6651 independent reflections
  • 6047 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.105
  • S = 1.02
  • 6651 reflections
  • 423 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.43 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2303 Friedel pairs
  • Flack parameter: 0.06 (5)

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

Table 1
Selected torsion angles (°)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807055948/bi2249sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807055948/bi2249Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the EPSRC UK National Crystallography Service (University of Southampton) for the data collection.

supplementary crystallographic information

Comment

As part of our ongoing investigations of chiral, C2-symmetric catalysts (Marshall et al., 2004), the title compound, C15H22N4O2S2, an intermediate in such materials, has been synthesized and structurally characterized.

There are two molecules in the asymmetric unit (Figs. 1 & 2), both of which show the same, expected, atomic chirality: atoms C6, C7, C21 and C25 all have an S configuration. However, their conformations are distinctly different, as indicated by a comparison of C—C—N—C side-chain torsion angles for the two molecules (Table 1). The dihedral angles between the thio-imidazole rings are 81.59 (5)° and 67.04 (4)°, for the C1 and C16-containing molecules, respectively. This means that the C1 molecule shows no local symmetry, whereas the C16 molecule possesses local C2 symmetry about the axis running through C22 and the mid-point of the C21—C25 bond. The thio-imidazole rings of both molecules display typical geometrical parameters, with the C—S bond lengths significantly longer than that of an isolated C?S double bond (~1.60 Å), which can be correlated with the contribution of resonance structures involving the lone pair electrons of the adjacent N atoms (Williamson et al., 2006). Otherwise, the geometries of the two molecules may be regarded as normal.

The crystal packing exhibits intermolecular C—H···O and C—H···S contacts (Table 2), giving pseudo (100) sheets of molecules in the crystal (Fig. 3).

Experimental

A mixture of (4S,5S)-4,5-bis(1-methylimidazolium-3-methyl)-2,2-dimethyl-1,3- dioxolane dibromide (0.67 g, 1.48 mmol), sulfur (0.14 g, 4.45 mmol), methanol (17 ml), pyridine (1.5 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1 g, 6.53 mmol) was heated at 338 K for 18 h. Once cooled to room temperature, water (50 ml) was added, and the mixture was 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, loaded as a dichloromethane solution) to give the dithione (0.37 g, 70%) as a colourless solid which was recrystallized from ethanol to give colourless blocks (m.p. 442 K).

Refinement

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 about their local threefold axes to give the best fit to the electron density.

Figures

Fig. 1.
View of the molecular structures of C1 molecule showing 50% displacement ellipsoids. The H atoms are drawn as spheres of arbitrary radius.
Fig. 2.
View of the molecular structures of C16 molecule of showing 50% displacement ellipsoids. The H atoms are drawn as spheres of arbitrary radius.
Fig. 3.
Unit-cell packing with H atoms omitted for clarity.

Crystal data

C15H22N4O2S2F000 = 752
Mr = 354.49Dx = 1.327 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9330 reflections
a = 10.462 (2) Åθ = 2.9–27.5º
b = 8.6043 (17) ŵ = 0.31 mm1
c = 20.249 (4) ÅT = 123 (2) K
β = 103.19 (3)ºBlock, colourless
V = 1774.7 (6) Å30.18 × 0.16 × 0.16 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer6047 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Monochromator: graphiteθmax = 27.5º
T = 123(2) Kθmin = 3.1º
ω and [var phi] scansh = −13→13
Absorption correction: nonek = −10→11
13494 measured reflectionsl = −24→26
6651 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041  w = 1/[σ2(Fo2) + (0.0643P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.33 e Å3
6651 reflectionsΔρmin = −0.43 e Å3
423 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), with 2303 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.06 (5)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
S10.08821 (5)1.00232 (6)0.11169 (3)0.02403 (14)
S20.38790 (5)0.99782 (6)0.37475 (3)0.02505 (14)
O10.36101 (14)0.55181 (18)0.22141 (7)0.0253 (4)
O20.17411 (15)0.52668 (19)0.26106 (8)0.0277 (4)
N10.14301 (16)0.8059 (2)0.01597 (9)0.0217 (4)
N20.27338 (16)0.7767 (2)0.11545 (8)0.0194 (4)
N30.20925 (15)0.7609 (2)0.36360 (8)0.0200 (4)
N40.33053 (16)0.7879 (2)0.46509 (9)0.0218 (4)
C10.0455 (2)0.8683 (3)−0.04072 (10)0.0272 (5)
H1A0.07780.8597−0.08230.041*
H1B0.02930.9778−0.03210.041*
H1C−0.03650.8095−0.04590.041*
C20.16862 (19)0.8611 (2)0.08012 (10)0.0186 (4)
C30.2295 (2)0.6852 (3)0.01103 (11)0.0238 (5)
H30.23110.6262−0.02840.029*
C40.3105 (2)0.6679 (3)0.07280 (11)0.0264 (5)
H40.38000.59480.08490.032*
C50.34737 (19)0.8156 (3)0.18340 (10)0.0211 (5)
H5A0.32280.92170.19480.025*
H5B0.44210.81660.18360.025*
C60.32494 (19)0.7044 (3)0.23752 (10)0.0196 (4)
H60.38000.73640.28260.024*
C70.18308 (19)0.6860 (3)0.24267 (10)0.0205 (5)
H70.12420.70390.19690.025*
C80.2924 (2)0.4465 (3)0.25547 (11)0.0282 (5)
C90.2571 (3)0.3041 (3)0.21235 (13)0.0435 (6)
H9A0.20920.23130.23500.065*
H9B0.33740.25440.20550.065*
H9C0.20170.33370.16830.065*
C100.3730 (2)0.4109 (3)0.32569 (11)0.0332 (5)
H10A0.32130.34670.35000.050*
H10B0.39730.50830.35050.050*
H10C0.45260.35470.32220.050*
C110.1421 (2)0.7934 (3)0.29347 (10)0.0226 (5)
H11A0.16050.90210.28250.027*
H11B0.04620.78360.28900.027*
C120.30930 (19)0.8479 (2)0.40141 (10)0.0189 (4)
C130.1689 (2)0.6502 (3)0.40400 (11)0.0257 (5)
H130.10070.57640.38980.031*
C140.2442 (2)0.6661 (3)0.46713 (12)0.0266 (5)
H140.23930.60570.50570.032*
C150.4273 (2)0.8457 (3)0.52392 (11)0.0284 (5)
H15A0.38980.84300.56400.043*
H15B0.45110.95280.51550.043*
H15C0.50580.78000.53170.043*
S30.87712 (5)0.39985 (7)0.39791 (3)0.02640 (14)
S40.60998 (5)0.40522 (7)0.10499 (3)0.02620 (14)
O30.81983 (14)0.88017 (18)0.30275 (7)0.0240 (3)
O40.67952 (14)0.88153 (18)0.19686 (7)0.0240 (3)
N50.86003 (17)0.6053 (2)0.49936 (9)0.0223 (4)
N60.73945 (16)0.6687 (2)0.40117 (9)0.0205 (4)
N70.75542 (16)0.6655 (2)0.09850 (9)0.0208 (4)
N80.63092 (17)0.6032 (2)0.00141 (9)0.0217 (4)
C160.9544 (2)0.5263 (3)0.55250 (11)0.0275 (5)
H16A0.92450.53060.59490.041*
H16B1.04000.57740.55880.041*
H16C0.96220.41760.53960.041*
C170.8268 (2)0.5597 (3)0.43322 (11)0.0203 (5)
C180.7935 (2)0.7417 (3)0.50761 (12)0.0263 (5)
H180.79980.79710.54880.032*
C190.7189 (2)0.7803 (3)0.44683 (11)0.0253 (5)
H190.66250.86790.43700.030*
C200.68137 (19)0.6688 (3)0.32881 (10)0.0229 (5)
H20A0.60370.73790.31950.027*
H20B0.65140.56240.31430.027*
C210.77773 (19)0.7232 (3)0.28799 (10)0.0204 (4)
H210.85620.65340.29770.024*
C220.74960 (16)0.9822 (3)0.25008 (9)0.0227 (5)
C230.6504 (2)1.0807 (3)0.27491 (13)0.0309 (6)
H23A0.69581.14570.31280.046*
H23B0.58741.01300.29010.046*
H23C0.60361.14710.23790.046*
C240.8486 (2)1.0810 (3)0.22528 (13)0.0310 (6)
H24A0.89831.14370.26290.046*
H24B0.80271.14970.18890.046*
H24C0.90901.01360.20790.046*
C250.71825 (19)0.7234 (3)0.21188 (10)0.0204 (4)
H250.63860.65540.20200.024*
C260.8143 (2)0.6675 (3)0.17078 (10)0.0224 (5)
H26A0.89190.73670.17950.027*
H26B0.84450.56140.18570.027*
C270.66460 (19)0.5591 (3)0.06785 (11)0.0202 (4)
C280.7787 (2)0.7730 (3)0.05187 (12)0.0256 (5)
H280.83820.85800.06080.031*
C290.7014 (2)0.7348 (3)−0.00841 (12)0.0258 (5)
H290.69580.7879−0.05010.031*
C300.5324 (2)0.5260 (3)−0.05076 (10)0.0264 (5)
H30A0.55880.5308−0.09410.040*
H30B0.44760.5782−0.05520.040*
H30C0.52450.4171−0.03810.040*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0243 (3)0.0177 (3)0.0285 (3)0.0034 (3)0.0029 (2)−0.0032 (3)
S20.0272 (3)0.0182 (3)0.0301 (3)−0.0057 (3)0.0073 (2)0.0003 (3)
O10.0306 (8)0.0188 (9)0.0259 (8)0.0057 (6)0.0048 (6)0.0006 (6)
O20.0298 (8)0.0205 (9)0.0319 (8)−0.0071 (7)0.0054 (7)0.0011 (7)
N10.0245 (9)0.0183 (9)0.0218 (9)−0.0009 (8)0.0039 (7)0.0002 (8)
N20.0185 (8)0.0178 (10)0.0219 (9)0.0010 (7)0.0048 (7)−0.0012 (8)
N30.0166 (8)0.0209 (10)0.0230 (9)−0.0018 (7)0.0057 (7)0.0021 (8)
N40.0252 (9)0.0190 (10)0.0214 (9)0.0005 (8)0.0056 (7)0.0012 (8)
C10.0301 (12)0.0260 (13)0.0222 (11)−0.0031 (10)−0.0008 (9)0.0006 (9)
C20.0182 (10)0.0139 (11)0.0234 (10)−0.0045 (8)0.0039 (8)0.0005 (8)
C30.0295 (11)0.0179 (11)0.0266 (11)−0.0019 (9)0.0118 (9)−0.0061 (9)
C40.0279 (11)0.0212 (12)0.0321 (12)0.0046 (10)0.0111 (10)−0.0013 (10)
C50.0173 (10)0.0219 (11)0.0229 (10)−0.0015 (9)0.0020 (8)−0.0021 (9)
C60.0169 (10)0.0185 (11)0.0226 (10)0.0039 (8)0.0028 (8)−0.0008 (9)
C70.0167 (10)0.0205 (12)0.0225 (10)−0.0029 (9)0.0007 (8)0.0036 (9)
C80.0391 (13)0.0186 (12)0.0249 (11)−0.0020 (11)0.0031 (9)−0.0001 (9)
C90.0619 (17)0.0253 (14)0.0379 (14)−0.0018 (13)0.0005 (12)−0.0070 (12)
C100.0450 (13)0.0236 (12)0.0285 (11)0.0000 (11)0.0034 (10)0.0041 (10)
C110.0170 (10)0.0239 (12)0.0253 (11)0.0021 (9)0.0014 (8)0.0023 (10)
C120.0181 (10)0.0164 (11)0.0228 (10)0.0033 (8)0.0059 (8)−0.0005 (9)
C130.0278 (11)0.0199 (12)0.0310 (12)−0.0052 (9)0.0098 (9)0.0009 (10)
C140.0339 (12)0.0181 (12)0.0310 (12)−0.0002 (10)0.0142 (10)0.0059 (10)
C150.0286 (12)0.0314 (14)0.0229 (11)0.0019 (10)0.0010 (9)−0.0035 (10)
S30.0292 (3)0.0172 (3)0.0332 (3)−0.0004 (3)0.0078 (2)−0.0030 (2)
S40.0305 (3)0.0180 (3)0.0292 (3)−0.0008 (3)0.0048 (2)0.0018 (2)
O30.0226 (8)0.0207 (9)0.0260 (8)−0.0050 (7)−0.0001 (6)0.0003 (7)
O40.0235 (8)0.0215 (9)0.0243 (7)0.0050 (7)0.0000 (6)−0.0027 (7)
N50.0254 (9)0.0160 (10)0.0253 (9)0.0001 (8)0.0056 (8)0.0002 (8)
N60.0199 (8)0.0200 (10)0.0221 (9)−0.0016 (8)0.0057 (7)0.0013 (8)
N70.0191 (8)0.0209 (10)0.0223 (9)−0.0007 (8)0.0044 (7)−0.0029 (8)
N80.0244 (9)0.0175 (10)0.0219 (9)0.0012 (8)0.0028 (7)0.0000 (8)
C160.0285 (11)0.0221 (13)0.0291 (11)−0.0027 (10)0.0010 (9)0.0059 (10)
C170.0190 (10)0.0160 (11)0.0263 (11)−0.0039 (8)0.0060 (9)0.0025 (9)
C180.0306 (11)0.0218 (13)0.0279 (11)0.0010 (10)0.0095 (9)−0.0026 (10)
C190.0249 (11)0.0217 (12)0.0308 (12)0.0013 (9)0.0096 (9)−0.0017 (10)
C200.0193 (10)0.0235 (12)0.0253 (11)−0.0030 (9)0.0040 (9)0.0014 (9)
C210.0184 (10)0.0190 (11)0.0227 (11)−0.0001 (9)0.0025 (8)−0.0002 (9)
C220.0222 (11)0.0219 (14)0.0230 (11)0.0011 (8)0.0031 (9)0.0005 (8)
C230.0268 (12)0.0281 (14)0.0387 (13)−0.0025 (10)0.0091 (11)−0.0107 (11)
C240.0272 (12)0.0279 (13)0.0388 (13)0.0041 (10)0.0097 (11)0.0093 (11)
C250.0186 (10)0.0178 (11)0.0236 (11)−0.0005 (8)0.0023 (8)−0.0029 (9)
C260.0184 (10)0.0250 (12)0.0218 (10)0.0031 (9)0.0007 (8)−0.0029 (9)
C270.0202 (10)0.0154 (11)0.0252 (11)0.0034 (8)0.0055 (9)−0.0028 (9)
C280.0222 (11)0.0230 (13)0.0328 (12)0.0003 (9)0.0089 (9)0.0011 (10)
C290.0265 (11)0.0218 (13)0.0299 (12)−0.0003 (10)0.0078 (9)0.0021 (10)
C300.0309 (11)0.0199 (12)0.0252 (11)0.0017 (10)−0.0003 (9)−0.0064 (9)

Geometric parameters (Å, °)

S1—C21.685 (2)S3—C171.689 (2)
S2—C121.684 (2)S4—C271.686 (2)
O1—C61.425 (3)O3—C211.431 (3)
O1—C81.427 (3)O3—C221.446 (3)
O2—C71.429 (3)O4—C251.433 (3)
O2—C81.444 (3)O4—C221.445 (3)
N1—C21.351 (3)N5—C171.362 (3)
N1—C31.396 (3)N5—C181.394 (3)
N1—C11.454 (3)N5—C161.452 (3)
N2—C21.372 (3)N6—C171.366 (3)
N2—C41.387 (3)N6—C191.384 (3)
N2—C51.456 (2)N6—C201.452 (3)
N3—C121.370 (3)N7—C271.363 (3)
N3—C131.383 (3)N7—C281.383 (3)
N3—C111.460 (3)N7—C261.453 (3)
N4—C121.359 (3)N8—C271.364 (3)
N4—C141.390 (3)N8—C291.390 (3)
N4—C151.463 (3)N8—C301.457 (3)
C1—H1A0.980C16—H16A0.980
C1—H1B0.980C16—H16B0.980
C1—H1C0.980C16—H16C0.980
C3—C41.349 (3)C18—C191.340 (3)
C3—H30.950C18—H180.950
C4—H40.950C19—H190.950
C5—C61.513 (3)C20—C211.516 (3)
C5—H5A0.990C20—H20A0.990
C5—H5B0.990C20—H20B0.990
C6—C71.520 (3)C21—C251.525 (3)
C6—H61.000C21—H211.000
C7—C111.516 (3)C22—C241.512 (3)
C7—H71.000C22—C231.512 (3)
C8—C91.501 (3)C23—H23A0.980
C8—C101.510 (3)C23—H23B0.980
C9—H9A0.980C23—H23C0.980
C9—H9B0.980C24—H24A0.980
C9—H9C0.980C24—H24B0.980
C10—H10A0.980C24—H24C0.980
C10—H10B0.980C25—C261.521 (3)
C10—H10C0.980C25—H251.000
C11—H11A0.990C26—H26A0.990
C11—H11B0.990C26—H26B0.990
C13—C141.347 (3)C28—C291.342 (3)
C13—H130.950C28—H280.950
C14—H140.950C29—H290.950
C15—H15A0.980C30—H30A0.980
C15—H15B0.980C30—H30B0.980
C15—H15C0.980C30—H30C0.980
C6—O1—C8106.59 (16)C21—O3—C22109.79 (16)
C7—O2—C8109.22 (16)C25—O4—C22109.89 (16)
C2—N1—C3109.93 (17)C17—N5—C18109.75 (18)
C2—N1—C1125.35 (19)C17—N5—C16124.85 (19)
C3—N1—C1124.62 (18)C18—N5—C16125.36 (19)
C2—N2—C4109.65 (17)C17—N6—C19110.39 (18)
C2—N2—C5124.06 (17)C17—N6—C20124.06 (18)
C4—N2—C5125.43 (17)C19—N6—C20125.51 (18)
C12—N3—C13110.06 (17)C27—N7—C28110.58 (18)
C12—N3—C11125.14 (18)C27—N7—C26123.91 (18)
C13—N3—C11124.29 (18)C28—N7—C26125.46 (18)
C12—N4—C14110.34 (18)C27—N8—C29109.96 (18)
C12—N4—C15125.21 (19)C27—N8—C30124.70 (19)
C14—N4—C15124.42 (19)C29—N8—C30125.32 (19)
N1—C1—H1A109.5N5—C16—H16A109.5
N1—C1—H1B109.5N5—C16—H16B109.5
H1A—C1—H1B109.5H16A—C16—H16B109.5
N1—C1—H1C109.5N5—C16—H16C109.5
H1A—C1—H1C109.5H16A—C16—H16C109.5
H1B—C1—H1C109.5H16B—C16—H16C109.5
N1—C2—N2105.93 (18)N5—C17—N6105.20 (18)
N1—C2—S1127.72 (16)N5—C17—S3128.06 (17)
N2—C2—S1126.35 (16)N6—C17—S3126.71 (16)
C4—C3—N1107.20 (19)C19—C18—N5107.5 (2)
C4—C3—H3126.4C19—C18—H18126.2
N1—C3—H3126.4N5—C18—H18126.2
C3—C4—N2107.28 (19)C18—C19—N6107.1 (2)
C3—C4—H4126.4C18—C19—H19126.4
N2—C4—H4126.4N6—C19—H19126.4
N2—C5—C6113.73 (18)N6—C20—C21111.90 (17)
N2—C5—H5A108.8N6—C20—H20A109.2
C6—C5—H5A108.8C21—C20—H20A109.2
N2—C5—H5B108.8N6—C20—H20B109.2
C6—C5—H5B108.8C21—C20—H20B109.2
H5A—C5—H5B107.7H20A—C20—H20B107.9
O1—C6—C5108.90 (17)O3—C21—C20112.87 (18)
O1—C6—C7103.50 (15)O3—C21—C25104.21 (15)
C5—C6—C7115.53 (16)C20—C21—C25112.49 (18)
O1—C6—H6109.6O3—C21—H21109.0
C5—C6—H6109.6C20—C21—H21109.0
C7—C6—H6109.6C25—C21—H21109.0
O2—C7—C11111.25 (17)O4—C22—O3105.8 (2)
O2—C7—C6103.95 (16)O4—C22—C24111.03 (16)
C11—C7—C6114.51 (17)O3—C22—C24108.37 (16)
O2—C7—H7109.0O4—C22—C23108.29 (16)
C11—C7—H7109.0O3—C22—C23111.51 (16)
C6—C7—H7109.0C24—C22—C23111.7 (2)
O1—C8—O2105.64 (18)C22—C23—H23A109.5
O1—C8—C9108.73 (19)C22—C23—H23B109.5
O2—C8—C9109.5 (2)H23A—C23—H23B109.5
O1—C8—C10110.47 (18)C22—C23—H23C109.5
O2—C8—C10109.11 (18)H23A—C23—H23C109.5
C9—C8—C10113.1 (2)H23B—C23—H23C109.5
C8—C9—H9A109.5C22—C24—H24A109.5
C8—C9—H9B109.5C22—C24—H24B109.5
H9A—C9—H9B109.5H24A—C24—H24B109.5
C8—C9—H9C109.5C22—C24—H24C109.5
H9A—C9—H9C109.5H24A—C24—H24C109.5
H9B—C9—H9C109.5H24B—C24—H24C109.5
C8—C10—H10A109.5O4—C25—C26111.97 (18)
C8—C10—H10B109.5O4—C25—C21104.23 (15)
H10A—C10—H10B109.5C26—C25—C21112.61 (18)
C8—C10—H10C109.5O4—C25—H25109.3
H10A—C10—H10C109.5C26—C25—H25109.3
H10B—C10—H10C109.5C21—C25—H25109.3
N3—C11—C7113.29 (18)N7—C26—C25111.96 (17)
N3—C11—H11A108.9N7—C26—H26A109.2
C7—C11—H11A108.9C25—C26—H26A109.2
N3—C11—H11B108.9N7—C26—H26B109.2
C7—C11—H11B108.9C25—C26—H26B109.2
H11A—C11—H11B107.7H26A—C26—H26B107.9
N4—C12—N3105.17 (17)N7—C27—N8105.00 (18)
N4—C12—S2127.51 (17)N7—C27—S4126.63 (16)
N3—C12—S2127.32 (16)N8—C27—S4128.35 (17)
C14—C13—N3107.47 (19)C29—C28—N7107.1 (2)
C14—C13—H13126.3C29—C28—H28126.5
N3—C13—H13126.3N7—C28—H28126.5
C13—C14—N4106.9 (2)C28—C29—N8107.4 (2)
C13—C14—H14126.5C28—C29—H29126.3
N4—C14—H14126.5N8—C29—H29126.3
N4—C15—H15A109.5N8—C30—H30A109.5
N4—C15—H15B109.5N8—C30—H30B109.5
H15A—C15—H15B109.5H30A—C30—H30B109.5
N4—C15—H15C109.5N8—C30—H30C109.5
H15A—C15—H15C109.5H30A—C30—H30C109.5
H15B—C15—H15C109.5H30B—C30—H30C109.5
C3—N1—C2—N21.1 (2)C18—N5—C17—N6−0.1 (2)
C1—N1—C2—N2−175.43 (18)C16—N5—C17—N6−178.01 (18)
C3—N1—C2—S1−177.95 (15)C18—N5—C17—S3−178.07 (16)
C1—N1—C2—S15.5 (3)C16—N5—C17—S34.0 (3)
C4—N2—C2—N1−0.9 (2)C19—N6—C17—N50.0 (2)
C5—N2—C2—N1168.98 (18)C20—N6—C17—N5177.77 (18)
C4—N2—C2—S1178.19 (16)C19—N6—C17—S3178.02 (16)
C5—N2—C2—S1−11.9 (3)C20—N6—C17—S3−4.2 (3)
C2—N1—C3—C4−0.9 (2)C17—N5—C18—C190.1 (3)
C1—N1—C3—C4175.6 (2)C16—N5—C18—C19178.1 (2)
N1—C3—C4—N20.3 (2)N5—C18—C19—N6−0.1 (2)
C2—N2—C4—C30.3 (2)C17—N6—C19—C180.1 (2)
C5—N2—C4—C3−169.37 (19)C20—N6—C19—C18−177.65 (19)
C2—N2—C5—C6109.2 (2)C21—C20—N6—C17−75.4 (3)
C7—C11—N3—C12104.4 (2)C25—C26—N7—C27−72.9 (3)
C4—N2—C5—C6−82.5 (2)C19—N6—C20—C21102.0 (2)
C8—O1—C6—C5−157.40 (16)C22—O3—C21—C20−101.23 (19)
C8—O1—C6—C7−33.99 (19)C22—O3—C21—C2521.1 (2)
N2—C5—C6—O158.9 (2)N6—C20—C21—O3−62.6 (2)
N2—C5—C6—C7−57.0 (2)N6—C20—C21—C25179.80 (17)
C8—O2—C7—C11−133.47 (17)C25—O4—C22—O3−7.34 (18)
C8—O2—C7—C6−9.7 (2)C25—O4—C22—C24110.0 (2)
O1—C6—C7—O226.5 (2)C25—O4—C22—C23−127.0 (2)
C5—C6—C7—O2145.48 (17)C21—O3—C22—O4−9.39 (18)
O1—C6—C7—C11148.13 (17)C21—O3—C22—C24−128.53 (19)
C5—C6—C7—C11−92.9 (2)C21—O3—C22—C23108.1 (2)
C6—O1—C8—O228.40 (19)C22—O4—C25—C26−102.18 (19)
C6—O1—C8—C9145.9 (2)C22—O4—C25—C2119.8 (2)
C6—O1—C8—C10−89.5 (2)O3—C21—C25—O4−24.7 (2)
C7—O2—C8—O1−10.7 (2)C20—C21—C25—O497.95 (19)
C7—O2—C8—C9−127.6 (2)O3—C21—C25—C2696.94 (19)
C7—O2—C8—C10108.05 (19)C20—C21—C25—C26−140.5 (2)
C13—N3—C11—C7−84.7 (2)C28—N7—C26—C25104.3 (2)
O2—C7—C11—N351.3 (2)O4—C25—C26—N7−64.0 (2)
C6—C7—C11—N3−66.2 (2)C21—C25—C26—N7178.92 (17)
C14—N4—C12—N3−0.5 (2)C28—N7—C27—N8−0.5 (2)
C15—N4—C12—N3−178.67 (19)C26—N7—C27—N8177.06 (18)
C14—N4—C12—S2178.97 (16)C28—N7—C27—S4178.30 (16)
C15—N4—C12—S20.8 (3)C26—N7—C27—S4−4.1 (3)
C13—N3—C12—N40.6 (2)C29—N8—C27—N70.4 (2)
C11—N3—C12—N4172.64 (18)C30—N8—C27—N7−177.74 (18)
C13—N3—C12—S2−178.82 (16)C29—N8—C27—S4−178.38 (16)
C11—N3—C12—S2−6.8 (3)C30—N8—C27—S43.5 (3)
C12—N3—C13—C14−0.6 (2)C27—N7—C28—C290.4 (2)
C11—N3—C13—C14−172.64 (19)C26—N7—C28—C29−177.09 (19)
N3—C13—C14—N40.2 (2)N7—C28—C29—N8−0.2 (2)
C12—N4—C14—C130.2 (2)C27—N8—C29—C28−0.1 (2)
C15—N4—C14—C13178.4 (2)C30—N8—C29—C28178.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···S40.952.863.797 (2)170
C5—H5B···O40.992.503.470 (3)166
C11—H11B···O3i0.992.583.500 (3)154
C13—H13···S3i0.952.833.715 (2)156
C28—H28···S1ii0.952.873.749 (2)155

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2249).

References

  • Blessing, R. H. (1995). Acta Cryst. A51, 33–38. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Marshall, C., Ward, M. F. & Harrison, W. T. A. (2004). Tetrahedron Lett.45, 5703–5706.
  • Nonius (1998). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Williamson, C., Storey, J. M. D. & Harrison, W. T. A. (2006). J. Chem. Crystallogr.36, 277–282.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography