Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024257/lh2391sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024257/lh2391Isup2.hkl |
CCDC reference: 651447
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.
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.
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).
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.
C24H18N2S3 | F(000) = 896 |
Mr = 430.62 | Dx = 1.430 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2095 (1) Å | Cell parameters from 4829 reflections |
b = 12.9738 (2) Å | θ = 5–28° |
c = 18.8054 (3) Å | µ = 0.39 mm−1 |
β = 93.2975 (7)° | T = 150 K |
V = 1999.62 (5) Å3 | Block, pink |
Z = 4 | 0.62 × 0.60 × 0.45 mm |
Bruker-Nonius KappaCCD diffractometer | 4734 reflections with I > −3.0σ(I) |
Graphite monochromator | Rint = 0.013 |
ω scans | θmax = 27.9°, θmin = 5.1° |
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) | h = −10→10 |
Tmin = 0.56, Tmax = 0.84 | k = −17→12 |
23179 measured reflections | l = −24→24 |
4734 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-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 reflections | Δρmax = 0.37 e Å−3 |
262 parameters | Δρmin = −0.26 e Å−3 |
0 restraints |
C24H18N2S3 | V = 1999.62 (5) Å3 |
Mr = 430.62 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 8.2095 (1) Å | µ = 0.39 mm−1 |
b = 12.9738 (2) Å | T = 150 K |
c = 18.8054 (3) Å | 0.62 × 0.60 × 0.45 mm |
β = 93.2975 (7)° |
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 = 0.84 | Rint = 0.013 |
23179 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.37 e Å−3 |
4734 reflections | Δρmin = −0.26 e Å−3 |
262 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.66751 (15) | 0.75552 (9) | 0.27352 (6) | 0.0190 | |
S2 | 0.68740 (4) | 0.88721 (2) | 0.261136 (17) | 0.0231 | |
C3 | 0.53408 (15) | 0.87515 (10) | 0.19411 (6) | 0.0197 | |
N4 | 0.47998 (13) | 0.78163 (8) | 0.18438 (6) | 0.0219 | |
N5 | 0.55794 (13) | 0.71174 (8) | 0.23113 (6) | 0.0216 | |
S6 | 0.46202 (4) | 0.98431 (2) | 0.148072 (17) | 0.0235 | |
C7 | 0.28616 (16) | 0.93037 (10) | 0.09599 (7) | 0.0236 | |
C8 | 0.19611 (15) | 1.02049 (9) | 0.06172 (7) | 0.0208 | |
C9 | 0.08118 (15) | 1.07858 (9) | 0.09984 (7) | 0.0201 | |
C10 | 0.00184 (15) | 1.16412 (9) | 0.06500 (7) | 0.0219 | |
C11 | 0.03773 (16) | 1.18887 (10) | −0.00596 (7) | 0.0254 | |
C12 | 0.14673 (17) | 1.13191 (11) | −0.04135 (7) | 0.0268 | |
C13 | 0.22634 (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 | |
C17 | 0.03962 (17) | 1.05441 (10) | 0.17013 (7) | 0.0260 | |
S18 | 0.78546 (4) | 0.69146 (2) | 0.340331 (17) | 0.0223 | |
C19 | 0.64192 (16) | 0.59002 (11) | 0.36317 (7) | 0.0251 | |
C20 | 0.72179 (15) | 0.52241 (10) | 0.42019 (7) | 0.0236 | |
C21 | 0.83252 (16) | 0.44238 (10) | 0.40272 (7) | 0.0244 | |
C22 | 0.89975 (17) | 0.37824 (11) | 0.45879 (8) | 0.0305 | |
C23 | 0.85668 (19) | 0.39678 (13) | 0.52956 (8) | 0.0373 | |
C24 | 0.75468 (19) | 0.47467 (14) | 0.54493 (8) | 0.0376 | |
C25 | 0.68700 (17) | 0.53818 (12) | 0.48984 (8) | 0.0304 | |
C26 | 1.0115 (2) | 0.29975 (12) | 0.44187 (11) | 0.0423 | |
C27 | 1.0555 (2) | 0.28529 (13) | 0.37410 (12) | 0.0480 | |
C28 | 0.9898 (2) | 0.34872 (12) | 0.31864 (10) | 0.0405 | |
C29 | 0.88061 (18) | 0.42487 (11) | 0.33260 (8) | 0.0294 | |
H71 | 0.2205 | 0.8932 | 0.1284 | 0.0285* | |
H72 | 0.3267 | 0.8841 | 0.0610 | 0.0293* | |
H111 | −0.0173 | 1.2450 | −0.0283 | 0.0310* | |
H121 | 0.1690 | 1.1490 | −0.0883 | 0.0323* | |
H131 | 0.2991 | 1.0088 | −0.0319 | 0.0288* | |
H141 | −0.1678 | 1.2785 | 0.0776 | 0.0339* | |
H151 | −0.2304 | 1.2365 | 0.1927 | 0.0414* | |
H161 | −0.0988 | 1.0958 | 0.2507 | 0.0388* | |
H171 | 0.0887 | 0.9967 | 0.1941 | 0.0308* | |
H191 | 0.5451 | 0.6233 | 0.3802 | 0.0303* | |
H192 | 0.6112 | 0.5516 | 0.3200 | 0.0304* | |
H231 | 0.9061 | 0.3540 | 0.5661 | 0.0446* | |
H241 | 0.7298 | 0.4877 | 0.5929 | 0.0460* | |
H251 | 0.6141 | 0.5924 | 0.5007 | 0.0368* | |
H261 | 1.0547 | 0.2582 | 0.4791 | 0.0508* | |
H271 | 1.1292 | 0.2343 | 0.3634 | 0.0573* | |
H281 | 1.0207 | 0.3378 | 0.2712 | 0.0485* | |
H291 | 0.8351 | 0.4674 | 0.2941 | 0.0348* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0188 (6) | 0.0181 (5) | 0.0200 (6) | 0.0025 (4) | 0.0010 (5) | 0.0018 (4) |
S2 | 0.02330 (16) | 0.01779 (15) | 0.02724 (17) | −0.00106 (11) | −0.00687 (12) | 0.00231 (11) |
C3 | 0.0196 (6) | 0.0220 (6) | 0.0175 (5) | 0.0032 (5) | 0.0000 (4) | 0.0007 (4) |
N4 | 0.0255 (5) | 0.0193 (5) | 0.0205 (5) | 0.0034 (4) | −0.0035 (4) | −0.0006 (4) |
N5 | 0.0232 (5) | 0.0178 (5) | 0.0233 (5) | 0.0028 (4) | −0.0030 (4) | 0.0005 (4) |
S6 | 0.02495 (17) | 0.01913 (15) | 0.02580 (16) | 0.00140 (12) | −0.00453 (12) | 0.00427 (12) |
C7 | 0.0264 (6) | 0.0184 (6) | 0.0253 (6) | 0.0035 (5) | −0.0057 (5) | −0.0002 (5) |
C8 | 0.0221 (6) | 0.0165 (5) | 0.0230 (6) | −0.0011 (5) | −0.0057 (5) | 0.0009 (5) |
C9 | 0.0203 (6) | 0.0157 (5) | 0.0237 (6) | −0.0021 (5) | −0.0041 (5) | 0.0015 (5) |
C10 | 0.0184 (6) | 0.0167 (5) | 0.0299 (6) | −0.0026 (5) | −0.0055 (5) | 0.0026 (5) |
C11 | 0.0251 (7) | 0.0191 (6) | 0.0308 (7) | −0.0035 (5) | −0.0095 (5) | 0.0075 (5) |
C12 | 0.0304 (7) | 0.0272 (7) | 0.0220 (6) | −0.0069 (5) | −0.0056 (5) | 0.0063 (5) |
C13 | 0.0262 (7) | 0.0235 (6) | 0.0235 (6) | −0.0016 (5) | −0.0024 (5) | −0.0006 (5) |
C14 | 0.0223 (6) | 0.0210 (6) | 0.0422 (8) | 0.0030 (5) | −0.0040 (6) | 0.0021 (6) |
C15 | 0.0284 (7) | 0.0299 (7) | 0.0447 (9) | 0.0030 (6) | 0.0070 (6) | −0.0028 (6) |
C16 | 0.0356 (8) | 0.0314 (7) | 0.0307 (7) | −0.0021 (6) | 0.0084 (6) | 0.0015 (6) |
C17 | 0.0306 (7) | 0.0207 (6) | 0.0263 (6) | −0.0003 (5) | −0.0012 (5) | 0.0039 (5) |
S18 | 0.01965 (15) | 0.02174 (15) | 0.02509 (16) | 0.00028 (11) | −0.00367 (12) | 0.00625 (12) |
C19 | 0.0203 (6) | 0.0272 (6) | 0.0275 (7) | −0.0015 (5) | −0.0013 (5) | 0.0076 (5) |
C20 | 0.0193 (6) | 0.0244 (6) | 0.0265 (6) | −0.0049 (5) | −0.0026 (5) | 0.0078 (5) |
C21 | 0.0209 (6) | 0.0213 (6) | 0.0301 (7) | −0.0058 (5) | −0.0052 (5) | 0.0067 (5) |
C22 | 0.0245 (7) | 0.0255 (7) | 0.0402 (8) | −0.0082 (5) | −0.0099 (6) | 0.0130 (6) |
C23 | 0.0303 (8) | 0.0433 (9) | 0.0367 (8) | −0.0142 (7) | −0.0125 (6) | 0.0226 (7) |
C24 | 0.0316 (8) | 0.0547 (10) | 0.0259 (7) | −0.0142 (7) | −0.0028 (6) | 0.0130 (7) |
C25 | 0.0243 (7) | 0.0377 (8) | 0.0291 (7) | −0.0058 (6) | 0.0004 (5) | 0.0066 (6) |
C26 | 0.0357 (8) | 0.0253 (7) | 0.0640 (11) | −0.0010 (6) | −0.0131 (8) | 0.0152 (7) |
C27 | 0.0406 (9) | 0.0253 (8) | 0.0768 (13) | 0.0082 (7) | −0.0075 (9) | −0.0022 (8) |
C28 | 0.0398 (9) | 0.0309 (8) | 0.0507 (10) | 0.0020 (7) | 0.0015 (7) | −0.0079 (7) |
C29 | 0.0301 (7) | 0.0241 (6) | 0.0335 (7) | −0.0026 (5) | −0.0029 (6) | 0.0021 (5) |
C1—S2 | 1.7332 (13) | C16—C17 | 1.369 (2) |
C1—N5 | 1.2981 (16) | C16—H161 | 0.942 |
C1—S18 | 1.7512 (12) | C17—H171 | 0.952 |
S2—C3 | 1.7364 (12) | S18—C19 | 1.8339 (13) |
C3—N4 | 1.3013 (16) | C19—C20 | 1.5061 (17) |
C3—S6 | 1.7453 (12) | C19—H191 | 0.974 |
N4—N5 | 1.3929 (14) | C19—H192 | 0.973 |
S6—C7 | 1.8360 (13) | C20—C21 | 1.4306 (19) |
C7—C8 | 1.5080 (17) | C20—C25 | 1.372 (2) |
C7—H71 | 0.966 | C21—C22 | 1.4290 (18) |
C7—H72 | 0.964 | C21—C29 | 1.416 (2) |
C8—C9 | 1.4317 (18) | C22—C23 | 1.417 (2) |
C8—C13 | 1.3725 (18) | C22—C26 | 1.419 (2) |
C9—C10 | 1.4269 (17) | C23—C24 | 1.354 (3) |
C9—C17 | 1.4192 (18) | C23—H231 | 0.956 |
C10—C11 | 1.4198 (19) | C24—C25 | 1.412 (2) |
C10—C14 | 1.4178 (19) | C24—H241 | 0.952 |
C11—C12 | 1.363 (2) | C25—H251 | 0.953 |
C11—H111 | 0.942 | C26—C27 | 1.357 (3) |
C12—C13 | 1.4133 (18) | C26—H261 | 0.937 |
C12—H121 | 0.939 | C27—C28 | 1.411 (3) |
C13—H131 | 0.929 | C27—H271 | 0.927 |
C14—C15 | 1.365 (2) | C28—C29 | 1.370 (2) |
C14—H141 | 0.958 | C28—H281 | 0.951 |
C15—C16 | 1.414 (2) | C29—H291 | 0.968 |
C15—H151 | 0.959 | ||
S2—C1—N5 | 114.59 (9) | C17—C16—H161 | 120.6 |
S2—C1—S18 | 120.78 (7) | C9—C17—C16 | 121.04 (12) |
N5—C1—S18 | 124.61 (10) | C9—C17—H171 | 119.8 |
C1—S2—C3 | 86.49 (6) | C16—C17—H171 | 119.2 |
S2—C3—N4 | 114.42 (9) | C1—S18—C19 | 99.93 (6) |
S2—C3—S6 | 119.86 (7) | S18—C19—C20 | 108.99 (9) |
N4—C3—S6 | 125.70 (10) | S18—C19—H191 | 107.9 |
C3—N4—N5 | 112.18 (10) | C20—C19—H191 | 110.7 |
N4—N5—C1 | 112.32 (10) | S18—C19—H192 | 108.1 |
C3—S6—C7 | 100.90 (6) | C20—C19—H192 | 112.1 |
S6—C7—C8 | 106.47 (8) | H191—C19—H192 | 108.9 |
S6—C7—H71 | 107.7 | C19—C20—C21 | 121.03 (12) |
C8—C7—H71 | 112.3 | C19—C20—C25 | 119.13 (13) |
S6—C7—H72 | 108.0 | C21—C20—C25 | 119.84 (12) |
C8—C7—H72 | 111.8 | C20—C21—C22 | 118.47 (13) |
H71—C7—H72 | 110.3 | C20—C21—C29 | 123.03 (12) |
C7—C8—C9 | 121.01 (11) | C22—C21—C29 | 118.49 (13) |
C7—C8—C13 | 119.27 (12) | C21—C22—C23 | 119.18 (14) |
C9—C8—C13 | 119.71 (11) | C21—C22—C26 | 118.66 (15) |
C8—C9—C10 | 118.43 (12) | C23—C22—C26 | 122.14 (14) |
C8—C9—C17 | 123.42 (11) | C22—C23—C24 | 121.19 (13) |
C10—C9—C17 | 118.14 (12) | C22—C23—H231 | 117.3 |
C9—C10—C11 | 119.57 (12) | C24—C23—H231 | 121.4 |
C9—C10—C14 | 119.25 (12) | C23—C24—C25 | 120.05 (15) |
C11—C10—C14 | 121.17 (12) | C23—C24—H241 | 120.2 |
C10—C11—C12 | 120.92 (12) | C25—C24—H241 | 119.7 |
C10—C11—H111 | 118.3 | C24—C25—C20 | 121.24 (15) |
C12—C11—H111 | 120.8 | C24—C25—H251 | 119.9 |
C11—C12—C13 | 119.66 (12) | C20—C25—H251 | 118.9 |
C11—C12—H121 | 120.0 | C22—C26—C27 | 121.34 (15) |
C13—C12—H121 | 120.4 | C22—C26—H261 | 117.9 |
C12—C13—C8 | 121.71 (13) | C27—C26—H261 | 120.8 |
C12—C13—H131 | 118.7 | C26—C27—C28 | 120.16 (16) |
C8—C13—H131 | 119.6 | C26—C27—H271 | 121.0 |
C10—C14—C15 | 121.17 (13) | C28—C27—H271 | 118.8 |
C10—C14—H141 | 118.8 | C27—C28—C29 | 120.37 (17) |
C15—C14—H141 | 120.0 | C27—C28—H281 | 119.7 |
C14—C15—C16 | 119.67 (14) | C29—C28—H281 | 119.9 |
C14—C15—H151 | 119.6 | C21—C29—C28 | 120.98 (14) |
C16—C15—H151 | 120.8 | C21—C29—H291 | 119.2 |
C15—C16—C17 | 120.73 (14) | C28—C29—H291 | 119.8 |
C15—C16—H161 | 118.7 |
Experimental details
Crystal data | |
Chemical formula | C24H18N2S3 |
Mr | 430.62 |
Crystal system, space group | Monoclinic, 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) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.39 |
Crystal size (mm) | 0.62 × 0.60 × 0.45 |
Data collection | |
Diffractometer | Bruker-Nonius KappaCCD |
Absorption correction | Multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.56, 0.84 |
No. of measured, independent and observed [I > −3.0σ(I)] reflections | 23179, 4734, 4734 |
Rint | 0.013 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.072, 0.98 |
No. of reflections | 4734 |
No. of parameters | 262 |
H-atom treatment | H-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.
S6—C7 | 1.8360 (13) | S18—C19 | 1.8339 (13) |
S6—C7—C8 | 106.47 (8) | C1—S18—C19 | 99.93 (6) |
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].