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Acta Cryst. (2007). E63, o2913
https://doi.org/10.1107/S1600536807024257
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2,5-Bis(2-naphthylmethylsulfanyl)-1-thia-3,4-diaza­cyclo­penta-2,5-diene

F. N.-F. How, D. J. Watkin, K. A. Crouse and M. I. M. Tahir
The title mol­ecule, C24H18N2S3, consists of three essentially planar fragments viz. two methyl­naphthalene groups and a five-membered thia­diazole ring. The dihedral angles between the two methyl­naphthalene groups and the central 1-thia-3,4-diaza­cyclo­penta-2,5-diene group are 78.9 (1) and 68.8 (1)°. In the crystal structure, π-π stacking inter­actions exist between pairs of symmetry-related naphthalene fragments with an inter­planar separation of 3.35 Å. All bond lengths and angles are comparable with previous reports except that both C—S bond lengths are slightly longer than normal. In addition, the C—S—C and S—C—C bond angles appear to be smaller than normal and this could be due to the steric hindrance of the methylnaphthalene fragments.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024257/lh2391sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024257/lh2391Isup2.hkl
Contains datablock I

CCDC reference: 651447

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.072
  • Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found




Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.560     0.840
            Tmin(prime) and Tmax expected:      0.782     0.841
            RR(prime) =      0.717
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.71


Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?


   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Crystallization of S-substituted dithiocarbazate or its derivatives may sometimes lead to unexpected compounds (Tarafder, Azahari et al., 2000; Tarafder, Saravanan et al., 2000]. These unexpected products are usually cyclized with the formation of a 5-membered thiazole-like ring. This could be due to either that solvent used for crystallization interacts with the dithiocarbzate compound or the compounds are simply unstable and tend to cyclize in solution. The title compound (see Fig. 1 for the molecular structure) was obtained unintensionally upon crystallization.

The bond length of N4—N5 [1.3929 (14) Å] is comparable to another similar compound derived from S-benzyldithiocarbazate (1.391 (3) Å; Tarafder, Saravanan et al., 2000). The bond length of N5—C1[1.2981 (16) Å] and N4—C3[1.3013 (16) Å] are characteristic of a normal C=N bond (Allen et al., 1987). Bond distances of C19—S18 [1.8339 (13) Å] and S6—C7 [1.8360 (13) Å] are slightly longer than previous literature values [1.816 (2)Å and 1.813 (3) Å; Tarafder, Saravanan et al., 2000].

The bond angles of the central 5-membered ring are comparable to the previous literature values (Tarafder, Saravanan et al., 2000). The smaller angles of C1—S18—C19 [99.93 (6)°] and S6—C7—C8 [106.47 (8)°] compared to literature values [101.04 (10)° and 109.31 (18)°; Tarafder, Saravanan et al., 2000) may be due to steric hindrance of the methyl naphthalene rings.

A TLS analysis of the anisotropic atomic displacement parameters for the naphthalene fragment C19 to C29 show that it is undergoing substantial libration about the bond S18—C19 (mean square displacement 11.7 Å2).

Molecules of the title compound are packed in diagonal layers along the b axis [Fig. 2]. Atom S18 overlaps a 5 membered thiazole-liked ring with a distance of 3.28 Å, leading to a π-π stacking interaction between S18 with the 5-membered ring situated in the middle of the two symmetry related methyl naphthalene fragments of an adjacent molecule [Fig. 3].

The naphthalene fragments at each end of the molecule are parallel to and overlap with the corresponding napthalene fragments in symmetry realted molecules, with an interplanar separation of 3.35Å [Fig. 4 and Fig. 5].

Related literature top

Similar compounds have been discovered unintentionally by crystallization of dithiocarbazate compounds (Tarafder, Azahari et al., 2000; Tarafder, Saravanan et al., 2000).

For related literature, see: Allen et al. (1987); Görbitz (1999); Shanmuga Sundara Raj et al. (2000).

Experimental top

The peparative procedure is modified from that previously reported for S-substituted dithiocarbazates (Shanmuga Sundara Raj et al., 2000), except substitution of benzyl chloride with 1-(chloromethyl) naphthalene (29.9 ml, 0.2 mol). The product expected to form was S-napthalen-2-ylmethyldithiocarbazate. Light pinkish crystals were obtained in acetonitrile solution. It was expected that the compound had cyclized in solution forming the title compound.

Refinement top

The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:1.51) reflect changes in the illuminated volume of the crystal, which were kept to a minimum, and were taken into account (Görbitz, 1999) by the inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints.

Structure description top

Crystallization of S-substituted dithiocarbazate or its derivatives may sometimes lead to unexpected compounds (Tarafder, Azahari et al., 2000; Tarafder, Saravanan et al., 2000]. These unexpected products are usually cyclized with the formation of a 5-membered thiazole-like ring. This could be due to either that solvent used for crystallization interacts with the dithiocarbzate compound or the compounds are simply unstable and tend to cyclize in solution. The title compound (see Fig. 1 for the molecular structure) was obtained unintensionally upon crystallization.

The bond length of N4—N5 [1.3929 (14) Å] is comparable to another similar compound derived from S-benzyldithiocarbazate (1.391 (3) Å; Tarafder, Saravanan et al., 2000). The bond length of N5—C1[1.2981 (16) Å] and N4—C3[1.3013 (16) Å] are characteristic of a normal C=N bond (Allen et al., 1987). Bond distances of C19—S18 [1.8339 (13) Å] and S6—C7 [1.8360 (13) Å] are slightly longer than previous literature values [1.816 (2)Å and 1.813 (3) Å; Tarafder, Saravanan et al., 2000].

The bond angles of the central 5-membered ring are comparable to the previous literature values (Tarafder, Saravanan et al., 2000). The smaller angles of C1—S18—C19 [99.93 (6)°] and S6—C7—C8 [106.47 (8)°] compared to literature values [101.04 (10)° and 109.31 (18)°; Tarafder, Saravanan et al., 2000) may be due to steric hindrance of the methyl naphthalene rings.

A TLS analysis of the anisotropic atomic displacement parameters for the naphthalene fragment C19 to C29 show that it is undergoing substantial libration about the bond S18—C19 (mean square displacement 11.7 Å2).

Molecules of the title compound are packed in diagonal layers along the b axis [Fig. 2]. Atom S18 overlaps a 5 membered thiazole-liked ring with a distance of 3.28 Å, leading to a π-π stacking interaction between S18 with the 5-membered ring situated in the middle of the two symmetry related methyl naphthalene fragments of an adjacent molecule [Fig. 3].

The naphthalene fragments at each end of the molecule are parallel to and overlap with the corresponding napthalene fragments in symmetry realted molecules, with an interplanar separation of 3.35Å [Fig. 4 and Fig. 5].

Similar compounds have been discovered unintentionally by crystallization of dithiocarbazate compounds (Tarafder, Azahari et al., 2000; Tarafder, Saravanan et al., 2000).

For related literature, see: Allen et al. (1987); Görbitz (1999); Shanmuga Sundara Raj et al. (2000).

Computing details top

Data collection: COLLECT (Nonius, 1997-2001).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
[Figure 2] Fig. 2. The packing of the molecules viewed along the b axis.
[Figure 3] Fig. 3. The π-π interaction between atom S18 and a symmetry related 5 membered ring.
[Figure 4] Fig. 4. The π-π interaction between a C8—C17 ring and a symmetry related C8—C17 ring.
[Figure 5] Fig. 5. The π-π interaction between a C20—C29 ring with a symmetry related C20—C29 ring.
2,5-Bis(2-naphthylmethylsulfanyl)-1-thia-3,4-diazacyclopenta-2,5-diene top
Crystal data top
C24H18N2S3F(000) = 896
Mr = 430.62Dx = 1.430 Mg m−3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 8.2095 (1) ÅCell parameters from 4829 reflections
b = 12.9738 (2) Åθ = 5–28°
c = 18.8054 (3) ŵ = 0.39 mm−1
β = 93.2975 (7)°T = 150 K
V = 1999.62 (5) Å3Block, pink
Z = 40.62 × 0.60 × 0.45 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer		4734 reflections with I > −3.0σ(I)
Graphite monochromatorRint = 0.013
ω scansθmax = 27.9°, θmin = 5.1°
Absorption correction: multi-scan
DENZO/SCALEPACK (Otwinowski & Minor, 1997)		h = −10→10
Tmin = 0.56, Tmax = 0.84k = −17→12
23179 measured reflectionsl = −24→24
4734 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.072 Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.02P)2 + 1.34P] ,
where P = (max(Fo2,0) + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
4734 reflectionsΔρmax = 0.37 e Å−3
262 parametersΔρmin = −0.26 e Å−3
0 restraints
Crystal data top
C24H18N2S3V = 1999.62 (5) Å3
Mr = 430.62Z = 4
Monoclinic, P21/aMo Kα radiation
a = 8.2095 (1) ŵ = 0.39 mm−1
b = 12.9738 (2) ÅT = 150 K
c = 18.8054 (3) Å0.62 × 0.60 × 0.45 mm
β = 93.2975 (7)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer		4734 independent reflections
Absorption correction: multi-scan
DENZO/SCALEPACK (Otwinowski & Minor, 1997)		4734 reflections with I > −3.0σ(I)
Tmin = 0.56, Tmax = 0.84Rint = 0.013
23179 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.072H-atom parameters constrained
S = 0.98Δρmax = 0.37 e Å−3
4734 reflectionsΔρmin = −0.26 e Å−3
262 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.66751 (15)0.75552 (9)0.27352 (6)0.0190
S20.68740 (4)0.88721 (2)0.261136 (17)0.0231
C30.53408 (15)0.87515 (10)0.19411 (6)0.0197
N40.47998 (13)0.78163 (8)0.18438 (6)0.0219
N50.55794 (13)0.71174 (8)0.23113 (6)0.0216
S60.46202 (4)0.98431 (2)0.148072 (17)0.0235
C70.28616 (16)0.93037 (10)0.09599 (7)0.0236
C80.19611 (15)1.02049 (9)0.06172 (7)0.0208
C90.08118 (15)1.07858 (9)0.09984 (7)0.0201
C100.00184 (15)1.16412 (9)0.06500 (7)0.0219
C110.03773 (16)1.18887 (10)−0.00596 (7)0.0254
C120.14673 (17)1.13191 (11)−0.04135 (7)0.0268
C130.22634 (16)1.04754 (10)−0.00684 (7)0.0246
C14−0.11338 (17)1.22204 (10)0.10167 (8)0.0287
C15−0.15069 (18)1.19678 (12)0.16931 (9)0.0341
C16−0.07261 (19)1.11184 (12)0.20385 (8)0.0323
C170.03962 (17)1.05441 (10)0.17013 (7)0.0260
S180.78546 (4)0.69146 (2)0.340331 (17)0.0223
C190.64192 (16)0.59002 (11)0.36317 (7)0.0251
C200.72179 (15)0.52241 (10)0.42019 (7)0.0236
C210.83252 (16)0.44238 (10)0.40272 (7)0.0244
C220.89975 (17)0.37824 (11)0.45879 (8)0.0305
C230.85668 (19)0.39678 (13)0.52956 (8)0.0373
C240.75468 (19)0.47467 (14)0.54493 (8)0.0376
C250.68700 (17)0.53818 (12)0.48984 (8)0.0304
C261.0115 (2)0.29975 (12)0.44187 (11)0.0423
C271.0555 (2)0.28529 (13)0.37410 (12)0.0480
C280.9898 (2)0.34872 (12)0.31864 (10)0.0405
C290.88061 (18)0.42487 (11)0.33260 (8)0.0294
H710.22050.89320.12840.0285*
H720.32670.88410.06100.0293*
H111−0.01731.2450−0.02830.0310*
H1210.16901.1490−0.08830.0323*
H1310.29911.0088−0.03190.0288*
H141−0.16781.27850.07760.0339*
H151−0.23041.23650.19270.0414*
H161−0.09881.09580.25070.0388*
H1710.08870.99670.19410.0308*
H1910.54510.62330.38020.0303*
H1920.61120.55160.32000.0304*
H2310.90610.35400.56610.0446*
H2410.72980.48770.59290.0460*
H2510.61410.59240.50070.0368*
H2611.05470.25820.47910.0508*
H2711.12920.23430.36340.0573*
H2811.02070.33780.27120.0485*
H2910.83510.46740.29410.0348*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0188 (6)0.0181 (5)0.0200 (6)0.0025 (4)0.0010 (5)0.0018 (4)
S20.02330 (16)0.01779 (15)0.02724 (17)−0.00106 (11)−0.00687 (12)0.00231 (11)
C30.0196 (6)0.0220 (6)0.0175 (5)0.0032 (5)0.0000 (4)0.0007 (4)
N40.0255 (5)0.0193 (5)0.0205 (5)0.0034 (4)−0.0035 (4)−0.0006 (4)
N50.0232 (5)0.0178 (5)0.0233 (5)0.0028 (4)−0.0030 (4)0.0005 (4)
S60.02495 (17)0.01913 (15)0.02580 (16)0.00140 (12)−0.00453 (12)0.00427 (12)
C70.0264 (6)0.0184 (6)0.0253 (6)0.0035 (5)−0.0057 (5)−0.0002 (5)
C80.0221 (6)0.0165 (5)0.0230 (6)−0.0011 (5)−0.0057 (5)0.0009 (5)
C90.0203 (6)0.0157 (5)0.0237 (6)−0.0021 (5)−0.0041 (5)0.0015 (5)
C100.0184 (6)0.0167 (5)0.0299 (6)−0.0026 (5)−0.0055 (5)0.0026 (5)
C110.0251 (7)0.0191 (6)0.0308 (7)−0.0035 (5)−0.0095 (5)0.0075 (5)
C120.0304 (7)0.0272 (7)0.0220 (6)−0.0069 (5)−0.0056 (5)0.0063 (5)
C130.0262 (7)0.0235 (6)0.0235 (6)−0.0016 (5)−0.0024 (5)−0.0006 (5)
C140.0223 (6)0.0210 (6)0.0422 (8)0.0030 (5)−0.0040 (6)0.0021 (6)
C150.0284 (7)0.0299 (7)0.0447 (9)0.0030 (6)0.0070 (6)−0.0028 (6)
C160.0356 (8)0.0314 (7)0.0307 (7)−0.0021 (6)0.0084 (6)0.0015 (6)
C170.0306 (7)0.0207 (6)0.0263 (6)−0.0003 (5)−0.0012 (5)0.0039 (5)
S180.01965 (15)0.02174 (15)0.02509 (16)0.00028 (11)−0.00367 (12)0.00625 (12)
C190.0203 (6)0.0272 (6)0.0275 (7)−0.0015 (5)−0.0013 (5)0.0076 (5)
C200.0193 (6)0.0244 (6)0.0265 (6)−0.0049 (5)−0.0026 (5)0.0078 (5)
C210.0209 (6)0.0213 (6)0.0301 (7)−0.0058 (5)−0.0052 (5)0.0067 (5)
C220.0245 (7)0.0255 (7)0.0402 (8)−0.0082 (5)−0.0099 (6)0.0130 (6)
C230.0303 (8)0.0433 (9)0.0367 (8)−0.0142 (7)−0.0125 (6)0.0226 (7)
C240.0316 (8)0.0547 (10)0.0259 (7)−0.0142 (7)−0.0028 (6)0.0130 (7)
C250.0243 (7)0.0377 (8)0.0291 (7)−0.0058 (6)0.0004 (5)0.0066 (6)
C260.0357 (8)0.0253 (7)0.0640 (11)−0.0010 (6)−0.0131 (8)0.0152 (7)
C270.0406 (9)0.0253 (8)0.0768 (13)0.0082 (7)−0.0075 (9)−0.0022 (8)
C280.0398 (9)0.0309 (8)0.0507 (10)0.0020 (7)0.0015 (7)−0.0079 (7)
C290.0301 (7)0.0241 (6)0.0335 (7)−0.0026 (5)−0.0029 (6)0.0021 (5)
Geometric parameters (Å, º) top
C1—S21.7332 (13)C16—C171.369 (2)
C1—N51.2981 (16)C16—H1610.942
C1—S181.7512 (12)C17—H1710.952
S2—C31.7364 (12)S18—C191.8339 (13)
C3—N41.3013 (16)C19—C201.5061 (17)
C3—S61.7453 (12)C19—H1910.974
N4—N51.3929 (14)C19—H1920.973
S6—C71.8360 (13)C20—C211.4306 (19)
C7—C81.5080 (17)C20—C251.372 (2)
C7—H710.966C21—C221.4290 (18)
C7—H720.964C21—C291.416 (2)
C8—C91.4317 (18)C22—C231.417 (2)
C8—C131.3725 (18)C22—C261.419 (2)
C9—C101.4269 (17)C23—C241.354 (3)
C9—C171.4192 (18)C23—H2310.956
C10—C111.4198 (19)C24—C251.412 (2)
C10—C141.4178 (19)C24—H2410.952
C11—C121.363 (2)C25—H2510.953
C11—H1110.942C26—C271.357 (3)
C12—C131.4133 (18)C26—H2610.937
C12—H1210.939C27—C281.411 (3)
C13—H1310.929C27—H2710.927
C14—C151.365 (2)C28—C291.370 (2)
C14—H1410.958C28—H2810.951
C15—C161.414 (2)C29—H2910.968
C15—H1510.959
S2—C1—N5114.59 (9)C17—C16—H161120.6
S2—C1—S18120.78 (7)C9—C17—C16121.04 (12)
N5—C1—S18124.61 (10)C9—C17—H171119.8
C1—S2—C386.49 (6)C16—C17—H171119.2
S2—C3—N4114.42 (9)C1—S18—C1999.93 (6)
S2—C3—S6119.86 (7)S18—C19—C20108.99 (9)
N4—C3—S6125.70 (10)S18—C19—H191107.9
C3—N4—N5112.18 (10)C20—C19—H191110.7
N4—N5—C1112.32 (10)S18—C19—H192108.1
C3—S6—C7100.90 (6)C20—C19—H192112.1
S6—C7—C8106.47 (8)H191—C19—H192108.9
S6—C7—H71107.7C19—C20—C21121.03 (12)
C8—C7—H71112.3C19—C20—C25119.13 (13)
S6—C7—H72108.0C21—C20—C25119.84 (12)
C8—C7—H72111.8C20—C21—C22118.47 (13)
H71—C7—H72110.3C20—C21—C29123.03 (12)
C7—C8—C9121.01 (11)C22—C21—C29118.49 (13)
C7—C8—C13119.27 (12)C21—C22—C23119.18 (14)
C9—C8—C13119.71 (11)C21—C22—C26118.66 (15)
C8—C9—C10118.43 (12)C23—C22—C26122.14 (14)
C8—C9—C17123.42 (11)C22—C23—C24121.19 (13)
C10—C9—C17118.14 (12)C22—C23—H231117.3
C9—C10—C11119.57 (12)C24—C23—H231121.4
C9—C10—C14119.25 (12)C23—C24—C25120.05 (15)
C11—C10—C14121.17 (12)C23—C24—H241120.2
C10—C11—C12120.92 (12)C25—C24—H241119.7
C10—C11—H111118.3C24—C25—C20121.24 (15)
C12—C11—H111120.8C24—C25—H251119.9
C11—C12—C13119.66 (12)C20—C25—H251118.9
C11—C12—H121120.0C22—C26—C27121.34 (15)
C13—C12—H121120.4C22—C26—H261117.9
C12—C13—C8121.71 (13)C27—C26—H261120.8
C12—C13—H131118.7C26—C27—C28120.16 (16)
C8—C13—H131119.6C26—C27—H271121.0
C10—C14—C15121.17 (13)C28—C27—H271118.8
C10—C14—H141118.8C27—C28—C29120.37 (17)
C15—C14—H141120.0C27—C28—H281119.7
C14—C15—C16119.67 (14)C29—C28—H281119.9
C14—C15—H151119.6C21—C29—C28120.98 (14)
C16—C15—H151120.8C21—C29—H291119.2
C15—C16—C17120.73 (14)C28—C29—H291119.8
C15—C16—H161118.7

Experimental details

Crystal data
Chemical formulaC24H18N2S3
Mr430.62
Crystal system, space groupMonoclinic, P21/a
Temperature (K)150
a, b, c (Å)8.2095 (1), 12.9738 (2), 18.8054 (3)
β (°) 93.2975 (7)
V (Å3)1999.62 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.39
Crystal size (mm)0.62 × 0.60 × 0.45
Data collection
DiffractometerBruker-Nonius KappaCCD
Absorption correctionMulti-scan
DENZO/SCALEPACK (Otwinowski & Minor, 1997)
Tmin, Tmax0.56, 0.84
No. of measured, independent and
observed [I > −3.0σ(I)] reflections		23179, 4734, 4734
Rint0.013
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.072, 0.98
No. of reflections4734
No. of parameters262
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.26

Computer programs: COLLECT (Nonius, 1997-2001)., DENZO/SCALEPACK (Otwinowski & Minor, 1997), DENZO/SCALEPACK, SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996), CRYSTALS.

Selected geometric parameters (Å, º) top
S6—C71.8360 (13)S18—C191.8339 (13)
S6—C7—C8106.47 (8)C1—S18—C1999.93 (6)
 

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