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In the title compound, C18H16N4OS, prepared by the reaction of 4-(acridin-9-yl)-1,1-di­methyl­thio­semicarbazide with methyl bromo­acetate, the acridine and thia­zolidine ring systems are both non-planar and, because of steric requirements, almost perpendicular, with a dihedral angle between their planes of 99.69 (6)°. C—H...O and C—H...π(arene) hydrogen bonds stabilize the crystal structure in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105005044/gd1369sup1.cif
Contains datablocks IV, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105005044/gd1369IVsup2.hkl
Contains datablock IV

CCDC reference: 269043

Comment top

Thiazole derivates, particularly 1,3-thiazolidin-4-ones, have a broad spectrum of biological activity (Singh et al., 1998; Liu & Anthonsen, 2000). Our continuing interest in 9-substituted acridine compounds, which may possess anticancer, chemiluminescent and intercalating properties (Kristian et al., 1998; Klika et al., 2001; Bernát et al., 2004; Demeunynck et al., 2001), led us to the synthesis of new acridin-9-yl-thiosemicarbazides and thiazolidinone derivatives. Besides the synthetic goal of this work, a presumed synergism of biological effects of both heterocyclic skeletons was another interesting point to study.

To obtain the target compounds, the reaction of acridin-9-yl isothiocyanate, (I), with 1,1- and 1,2-disubstituted hydrazines was used to give intermediate thiosemicarbazides, which were further cyclized with bromoacetic acid ester or bromide to obtain products of type IV (Fig. 1), (Vilková et al., 2005). Because of the presence of four nucleophilic centres in thiosemicarbazides, at least six types of isomeric five-membered heterocyclic structures could possibly be formed from the terminal cyclization step and/or subsequent possible rearrangements of the Dimroth type. An NMR proof of these structures is questionable because of ambiguities in assignments of cross peaks from two-dimensional H,C-correlation and NOESY spectra. Hence we have determined the structure of the selected model compound (IV), obtained by the reaction of 1,1-dimethyl-4-(acridin-9-yl)-thiosemicarbazide, (II), with methyl bromoacetate. The preparation of the studied compound involved the alkylation of the thiosemicarbazide to afford 1,1-dimethyl-4-(acridin-9-yl)-S-methoxycarbonylmethylene- isothiosemicarbazide hydrobromide, (III), by the attachment of the S atom of the thiosemicarbazide to a bromomethylene C atom (see scheme below).

A search of the Cambridge Structural Database (release of August 2004; Allen, 2002) showed that the title compound is the first example of a compound in which both acridine and thiazole ring systems are linked by an imine N atom. On the other hand, three derivatives of N-(acridin-9-yl)-1,4-benzoquinone monoimines have been structurally characterized (Clark et al., 1993), and there are two entries containing an imino-1,3-thiazolidin-4-one ring (Deepthi et al., 2001).

The acridine and thiazoline ring systems in (IV) both deviate significantly from planarity. Atom C2 exhibits the highest deviation, of 0.050 (3) Å from the mean plane through the 14 atoms of the acridine ring system, while in the thiazolidine ring, atom C15 deviates most from the mean plane [0.079 (3) Å]. The geometric parameters for the acridine ring system are similar to those found in phenyl-(acridin-9-yl)-amine (Leardini et al., 1998). The N2—C14 bond in the imine group is clearly shorter than the C9—N2 bond, indicating the double-bond character of the former. Similar distances were found in N-(9-acridinyl)-2-methoxy-1,4-benzoquinone monoimine (Clark et al., 1993). Owing to steric effects, the ring systems linked by imine atom N2 are almost perpendicular; the angle between the mean planes through the rings is 99.69 (6)°. The geometric parameters in the 1,3-thiazolidin-4-one ring are normal (Deepthi et al., 2001).

The packing of the individual molecules in the solid state is governed by two intermolecular C—H···O hydrogen bonds (Table 2) and a C—H···π(arene) hydrogen bond. Pairs of molecules of (IV) are linked by C15—H15···O1i [symmetry code: (i) −x, 1 − y, −z] hydrogen bonds, forming a ring that can be described by graph-set descriptor R22(8) (Berstein et al., 1995); moreover, each O1 atom participates in a C5—H5···O1ii [symmetry code: (ii) 1 + x, 1/2 − y, 1/2 + z] hydrogen bond, linking pairs of molecules into deformed planes. Finally, the planes interact by C18—H18···π(arene) hydrogen bonds.

Experimental top

Single crystals of (IV) in the form of bright-yellow needles suitable for X-ray studies were prepared by the following procedure. To a solution of 1,1-dimethyl hydrazine (0.120 g, 2 mmol) in anhydrous tetrahydrofuran (5 ml) was added, dropwise, acridin-9-yl isothiocyanate, (I) (Mazagová et al., 1994) (0.473 g, 2 mmol), dissolved in anhydrous tetrahydrofurane (5 ml). The reaction mixture was stirred at room temperature until isothiocyanate disappeared (monitored by thin-layer chromatography, eluant cyclohexane/ethyl acetate, 3:1); a precipitate of 1,1-dimethyl-4-(acridin-9-yl)-thiosemicarbazide, (II), was filtered off, dried and recrystallized from methanol/diethyl ether. Yield 60%, m.p. 466–469 K. 1H NMR (DMSO-d6): δ 2.76 (s, 6H, 2 × CH3), 7.50–8.25 (m, 8H, AcrH), 9.59 (br s, 1H, NH), 10.40 (br s, 1H, NH). To a suspension of thiosemicarbazide (II) (0.2 g, 0.67 mmol) in dry benzene (5 ml), methyl bromoacetate (0.103 g, 0.063 ml, 0.67 mmol) was slowly added. The solution was stirred at room temperature for 5 h, triethylamine (0.137 g, 0.188 ml, 1.35 mmol) was added, and stirring was continued for the next 2 h. The solution was filtered, the filtrate was evaporated and the residue was chromatographed using a column filled with silica gel (Merck 109385, 0.040–0.063 mm, 230–400 mesh, eluant ethyl acetate/cyclohexane, 4:1). To a saturated solution of crude (IV) in hot ethyl acetate, n-heptane was added to first turbidity and the product was left to crystallize for 2 h. Yield 31%, m.p. 475–477 K. 1H NMR (DMSO-d6): δ 3.16 (s, 6H, H-17,18), 3.93 (s, 2H, H-15), 7.53, 7.81, 8.00, 8.12 (m, 8H, AcrH); 13C NMR: δ: 30.8 (C-15), 42.7 (C-17,18), 117.0 (C-10,13), 123.9, 125.0, 129.2, 130.4 (AcrCH), 148.9 (C-11,12), 150.4 (C-9), 155.0? (C-14), 169.3 (C-16).

Refinement top

H atoms were freely refined with isotropic displacement parameters [C—H = 0.927 (19)–0.99 (3) Å).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Crystal Impact, 2000); software used to prepare material for publication: program (reference)?.

Figures top
[Figure 1] Fig. 1. A view of title compound, showing displacement ellipsoids at the 30% probability level.
2-(Acridin-9-ylimino)-3-dimethylamino-1,3-thiazolidin-4-one top
Crystal data top
C18H16N4OSF(000) = 704
Mr = 336.42Dx = 1.368 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 3118 reflections
a = 7.282 (5) Åθ = 2.1–25.0°
b = 19.456 (5) ŵ = 0.21 mm1
c = 11.954 (5) ÅT = 298 K
β = 105.326 (5)°Prism, yellow
V = 1633.4 (14) Å30.40 × 0.12 × 0.11 mm
Z = 4
Data collection top
Bruker SMART 1000
diffractometer
2867 independent reflections
Radiation source: fine-focus sealed tube1776 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 8.192 pixels/mm pixels mm-1θmax = 25.0°, θmin = 2.1°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker 1999)
k = 2315
Tmin = 0.787, Tmax = 0.977l = 1413
8245 measured reflections
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)] = 0.035All H-atom parameters refined
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0351P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.87(Δ/σ)max < 0.001
2867 reflectionsΔρmax = 0.17 e Å3
282 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (5)
Crystal data top
C18H16N4OSV = 1633.4 (14) Å3
Mr = 336.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.282 (5) ŵ = 0.21 mm1
b = 19.456 (5) ÅT = 298 K
c = 11.954 (5) Å0.40 × 0.12 × 0.11 mm
β = 105.326 (5)°
Data collection top
Bruker SMART 1000
diffractometer
2867 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker 1999)
1776 reflections with I > 2σ(I)
Tmin = 0.787, Tmax = 0.977Rint = 0.043
8245 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.079All H-atom parameters refined
S = 0.87Δρmax = 0.17 e Å3
2867 reflectionsΔρmin = 0.26 e Å3
282 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*/Ueq
S10.30409 (8)0.33825 (3)0.10522 (5)0.04651 (19)
O10.0638 (2)0.46877 (7)0.13032 (13)0.0483 (4)
N10.9133 (2)0.19210 (9)0.24539 (16)0.0469 (5)
N20.5803 (2)0.32560 (9)0.00933 (15)0.0429 (5)
N30.3238 (2)0.39793 (8)0.08672 (13)0.0366 (4)
N40.3830 (2)0.41895 (9)0.18407 (15)0.0455 (5)
C10.8163 (3)0.37932 (12)0.2086 (2)0.0454 (6)
H10.746 (3)0.4113 (10)0.1552 (19)0.053 (7)*
C20.9333 (3)0.40223 (14)0.3084 (2)0.0534 (6)
H20.937 (3)0.4497 (11)0.3278 (18)0.054 (7)*
C31.0400 (4)0.35528 (15)0.3900 (2)0.0590 (7)
H31.118 (3)0.3742 (10)0.4576 (18)0.051 (7)*
C41.0306 (3)0.28751 (14)0.3688 (2)0.0545 (7)
H41.101 (3)0.2557 (11)0.4238 (18)0.053 (6)*
C50.8044 (3)0.09588 (12)0.1220 (2)0.0524 (6)
H50.880 (3)0.0693 (10)0.1806 (17)0.043 (6)*
C60.6941 (4)0.06853 (14)0.0237 (2)0.0577 (7)
H60.698 (3)0.0202 (12)0.013 (2)0.071 (8)*
C70.5741 (4)0.11024 (14)0.0614 (2)0.0579 (7)
H70.500 (3)0.0891 (11)0.132 (2)0.071 (8)*
C80.5700 (3)0.17908 (14)0.0456 (2)0.0503 (6)
H80.490 (3)0.2086 (10)0.1031 (19)0.055 (7)*
C100.6839 (3)0.21028 (11)0.05681 (18)0.0401 (5)
C110.8028 (3)0.16762 (11)0.14404 (19)0.0425 (5)
C120.9123 (3)0.26043 (11)0.26361 (19)0.0430 (5)
C130.8002 (3)0.30799 (11)0.18189 (18)0.0382 (5)
C90.6831 (3)0.28118 (11)0.07814 (17)0.0390 (5)
C140.4236 (3)0.35167 (10)0.00316 (17)0.0360 (5)
C150.1063 (3)0.39156 (14)0.0298 (2)0.0475 (6)
H15A0.084 (3)0.4243 (10)0.0830 (17)0.049 (6)*
H15B0.002 (3)0.3631 (12)0.006 (2)0.074 (8)*
C160.1567 (3)0.42451 (11)0.07050 (18)0.0375 (5)
C170.5622 (4)0.45742 (17)0.1534 (3)0.0620 (7)
H17A0.672 (4)0.4260 (14)0.124 (2)0.104 (11)*
H17B0.577 (3)0.4775 (13)0.221 (2)0.088 (9)*
H17C0.555 (4)0.4913 (14)0.096 (3)0.101 (11)*
C180.3777 (4)0.36265 (17)0.2658 (2)0.0614 (8)
H18A0.254 (4)0.3391 (14)0.279 (2)0.101 (10)*
H18B0.396 (4)0.3843 (13)0.332 (2)0.089 (9)*
H18C0.485 (3)0.3316 (12)0.236 (2)0.074 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0474 (3)0.0548 (4)0.0396 (3)0.0042 (3)0.0155 (3)0.0075 (3)
O10.0462 (8)0.0419 (9)0.0533 (10)0.0114 (8)0.0070 (8)0.0025 (8)
N10.0419 (10)0.0473 (12)0.0483 (12)0.0060 (9)0.0062 (10)0.0068 (9)
N20.0399 (10)0.0490 (11)0.0394 (11)0.0099 (9)0.0100 (9)0.0082 (8)
N30.0349 (9)0.0414 (10)0.0344 (10)0.0050 (8)0.0107 (8)0.0058 (8)
N40.0438 (10)0.0550 (12)0.0395 (11)0.0016 (9)0.0141 (9)0.0091 (9)
C10.0446 (13)0.0468 (16)0.0451 (15)0.0034 (12)0.0122 (12)0.0079 (12)
C20.0570 (15)0.0489 (17)0.0545 (17)0.0058 (13)0.0151 (14)0.0017 (13)
C30.0520 (15)0.067 (2)0.0509 (17)0.0079 (14)0.0012 (13)0.0029 (14)
C40.0495 (15)0.0572 (18)0.0472 (16)0.0059 (13)0.0038 (12)0.0094 (13)
C50.0519 (15)0.0474 (17)0.0562 (18)0.0094 (13)0.0115 (14)0.0080 (14)
C60.0627 (16)0.0482 (17)0.0639 (19)0.0026 (14)0.0198 (15)0.0017 (14)
C70.0568 (16)0.0616 (19)0.0530 (17)0.0028 (14)0.0108 (14)0.0090 (14)
C80.0422 (13)0.0606 (18)0.0462 (16)0.0084 (12)0.0084 (12)0.0009 (13)
C100.0338 (11)0.0462 (14)0.0418 (14)0.0048 (10)0.0124 (11)0.0047 (10)
C110.0368 (11)0.0437 (14)0.0492 (14)0.0053 (11)0.0150 (11)0.0068 (11)
C120.0339 (11)0.0503 (15)0.0446 (14)0.0020 (11)0.0102 (10)0.0070 (11)
C130.0325 (11)0.0438 (14)0.0399 (13)0.0043 (10)0.0126 (10)0.0068 (10)
C90.0312 (11)0.0480 (14)0.0402 (13)0.0068 (10)0.0139 (10)0.0095 (10)
C140.0368 (11)0.0382 (13)0.0320 (12)0.0002 (10)0.0073 (9)0.0001 (10)
C150.0454 (14)0.0500 (16)0.0504 (16)0.0054 (13)0.0185 (13)0.0002 (12)
C160.0359 (11)0.0361 (13)0.0389 (13)0.0000 (10)0.0073 (10)0.0047 (10)
C170.0623 (18)0.064 (2)0.065 (2)0.0158 (16)0.0255 (16)0.0042 (16)
C180.0565 (18)0.089 (2)0.0413 (16)0.0088 (17)0.0165 (14)0.0089 (15)
Geometric parameters (Å, º) top
S1—C141.761 (2)C5—C111.421 (3)
S1—C151.810 (2)C5—H50.927 (19)
O1—C161.206 (2)C6—C71.410 (3)
N1—C121.347 (2)C6—H60.95 (2)
N1—C111.352 (3)C7—C81.354 (3)
N2—C141.269 (2)C7—H70.97 (2)
N2—C91.409 (2)C8—C101.421 (3)
N3—C161.383 (2)C8—H80.96 (2)
N3—C141.397 (2)C10—C91.403 (3)
N3—N41.404 (2)C10—C111.431 (3)
N4—C181.461 (3)C12—C131.434 (3)
N4—C171.465 (3)C13—C91.407 (3)
C1—C21.346 (3)C15—C161.488 (3)
C1—C131.422 (3)C15—H15A0.94 (2)
C1—H10.94 (2)C15—H15B0.94 (2)
C2—C31.410 (3)C17—H17A0.99 (3)
C2—H20.95 (2)C17—H17B0.93 (3)
C3—C41.341 (3)C17—H17C0.96 (3)
C3—H30.93 (2)C18—H18A0.99 (3)
C4—C121.424 (3)C18—H18B0.94 (3)
C4—H40.95 (2)C18—H18C0.98 (2)
C5—C61.345 (3)
C14—S1—C1591.81 (11)N1—C11—C5118.7 (2)
C12—N1—C11117.71 (18)N1—C11—C10123.4 (2)
C14—N2—C9120.77 (17)C5—C11—C10117.9 (2)
C16—N3—C14116.84 (17)N1—C12—C4118.7 (2)
C16—N3—N4118.78 (16)N1—C12—C13123.6 (2)
C14—N3—N4124.38 (16)C4—C12—C13117.7 (2)
N3—N4—C18112.08 (18)C9—C13—C1123.70 (19)
N3—N4—C17112.91 (19)C9—C13—C12117.69 (19)
C18—N4—C17114.5 (2)C1—C13—C12118.6 (2)
C2—C1—C13121.2 (2)C10—C9—C13119.62 (19)
C2—C1—H1119.1 (13)C10—C9—N2119.67 (19)
C13—C1—H1119.7 (13)C13—C9—N2120.40 (19)
C1—C2—C3120.2 (3)N2—C14—N3121.46 (18)
C1—C2—H2120.5 (13)N2—C14—S1127.64 (16)
C3—C2—H2119.1 (13)N3—C14—S1110.90 (14)
C4—C3—C2121.0 (3)C16—C15—S1108.36 (16)
C4—C3—H3122.7 (13)C16—C15—H15A112.0 (12)
C2—C3—H3116.3 (13)S1—C15—H15A107.8 (12)
C3—C4—C12121.3 (2)C16—C15—H15B111.7 (15)
C3—C4—H4121.2 (13)S1—C15—H15B107.8 (14)
C12—C4—H4117.4 (13)H15A—C15—H15B109.0 (19)
C6—C5—C11121.2 (2)O1—C16—N3124.10 (19)
C6—C5—H5122.7 (12)O1—C16—C15124.47 (19)
C11—C5—H5116.1 (12)N3—C16—C15111.43 (18)
C5—C6—C7121.0 (3)N4—C17—H17A110.8 (15)
C5—C6—H6118.8 (15)N4—C17—H17B107.5 (16)
C7—C6—H6120.2 (15)H17A—C17—H17B107 (2)
C8—C7—C6120.1 (3)N4—C17—H17C108.3 (16)
C8—C7—H7121.0 (14)H17A—C17—H17C111 (2)
C6—C7—H7118.9 (14)H17B—C17—H17C112 (2)
C7—C8—C10120.9 (2)N4—C18—H18A108.2 (16)
C7—C8—H8121.4 (12)N4—C18—H18B104.1 (16)
C10—C8—H8117.7 (12)H18A—C18—H18B114 (2)
C9—C10—C8123.2 (2)N4—C18—H18C110.1 (14)
C9—C10—C11117.9 (2)H18A—C18—H18C112 (2)
C8—C10—C11118.9 (2)H18B—C18—H18C108 (2)
C16—N3—N4—C18113.6 (2)N1—C12—C13—C1177.58 (19)
C14—N3—N4—C1866.9 (3)C4—C12—C13—C11.5 (3)
C16—N3—N4—C17115.3 (2)C8—C10—C9—C13179.95 (18)
C14—N3—N4—C1764.2 (3)C11—C10—C9—C131.3 (3)
C13—C1—C2—C31.3 (3)C8—C10—C9—N26.5 (3)
C1—C2—C3—C41.6 (4)C11—C10—C9—N2174.81 (16)
C2—C3—C4—C120.2 (4)C1—C13—C9—C10176.76 (19)
C11—C5—C6—C70.5 (4)C12—C13—C9—C101.8 (3)
C5—C6—C7—C80.7 (4)C1—C13—C9—N23.3 (3)
C6—C7—C8—C100.7 (4)C12—C13—C9—N2175.31 (17)
C7—C8—C10—C9179.2 (2)C14—N2—C9—C10105.3 (2)
C7—C8—C10—C110.5 (3)C14—N2—C9—C1381.2 (2)
C12—N1—C11—C5178.82 (18)C9—N2—C14—N3177.41 (18)
C12—N1—C11—C100.9 (3)C9—N2—C14—S11.5 (3)
C6—C5—C11—N1178.6 (2)C16—N3—C14—N2178.60 (18)
C6—C5—C11—C101.7 (3)N4—N3—C14—N21.0 (3)
C9—C10—C11—N10.1 (3)C16—N3—C14—S10.5 (2)
C8—C10—C11—N1178.61 (19)N4—N3—C14—S1179.95 (14)
C9—C10—C11—C5179.59 (18)C15—S1—C14—N2177.0 (2)
C8—C10—C11—C51.7 (3)C15—S1—C14—N34.03 (16)
C11—N1—C12—C4178.78 (19)C14—S1—C15—C167.05 (18)
C11—N1—C12—C130.3 (3)C14—N3—C16—O1174.02 (19)
C3—C4—C12—N1177.8 (2)N4—N3—C16—O15.6 (3)
C3—C4—C12—C131.3 (3)C14—N3—C16—C156.0 (2)
C2—C1—C13—C9178.8 (2)N4—N3—C16—C15174.34 (18)
C2—C1—C13—C120.2 (3)S1—C15—C16—O1171.51 (17)
N1—C12—C13—C91.1 (3)S1—C15—C16—N38.5 (2)
C4—C12—C13—C9179.86 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.93 (2)2.42 (2)3.311 (4)161.7 (17)
C15—H15A···O1ii0.94 (2)2.48 (2)3.339 (4)152.1 (16)
C18—H18B···Cgiii0.94 (3)2.97 (3)3.645 (4)131 (2)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC18H16N4OS
Mr336.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)7.282 (5), 19.456 (5), 11.954 (5)
β (°) 105.326 (5)
V3)1633.4 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.40 × 0.12 × 0.11
Data collection
DiffractometerBruker SMART 1000
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker 1999)
Tmin, Tmax0.787, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
8245, 2867, 1776
Rint0.043
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.079, 0.87
No. of reflections2867
No. of parameters282
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.17, 0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS86 (Sheldrick, 1985), SHELXL97 (Sheldrick, 1997), DIAMOND (Crystal Impact, 2000), program (reference)?.

Selected geometric parameters (Å, º) top
S1—C141.761 (2)N2—C91.409 (2)
S1—C151.810 (2)N3—C161.383 (2)
O1—C161.206 (2)N3—C141.397 (2)
N1—C121.347 (2)N3—N41.404 (2)
N1—C111.352 (3)N4—C181.461 (3)
N2—C141.269 (2)N4—C171.465 (3)
C14—S1—C1591.81 (11)C14—N3—N4124.38 (16)
C12—N1—C11117.71 (18)N3—N4—C18112.08 (18)
C14—N2—C9120.77 (17)N3—N4—C17112.91 (19)
C16—N3—C14116.84 (17)C18—N4—C17114.5 (2)
C16—N3—N4118.78 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.93 (2)2.42 (2)3.311 (4)161.7 (17)
C15—H15A···O1ii0.94 (2)2.48 (2)3.339 (4)152.1 (16)
C18—H18B···Cgiii0.94 (3)2.97 (3)3.645 (4)131 (2)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x, y+1/2, z1/2.
 

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