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Acta Cryst. (2007). E63, o3383    [ doi:10.1107/S1600536807031595 ]

1,1,3-Trioxo-2,3-dihydro-1,2-benzisothiazol-2-ylmethyl 4-phenylpiperazine-1-carbodithioate

M. Akkurt, S.P. Yalçin, Ö. Güzel, A. Salman and O. Büyükgüngör

Abstract top

In the title molecule, C19H19N3O3S3, the mean planes of the benzisothiazole system and the phenyl ring make a dihedral angle of 8.87 (8)°. The piperazine ring has a chair conformation. The crystal structure is stabilized by weak intermolecular C-H...O interactions and weak intramolecular C-H...S interactions.

Comment top

Considerable interest has been focused on dithiocarbamates which have shown to possess a broad spectrum of biological activities such as fungicidal (Ateş et al., 1995; Günay et al., 1999; Farghaly & Moharram, 1999; Xu et al., 2002) and antibacterial (Günay et al., 1999; Çapan et al., 1993; Imamura et al., 2001) effects. Dithiocarbamates are known also to be active as anticancer agents (Scozzafava et al., 2000; Cao et al., 2005). In our previous report (Güzel & Salman, 2006), (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl N,N-disubstituted dithiocarbamate and (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl O-alkyldithiocarbonate derivatives have been demonstrated to be potent antimycobacterial and antitumor activities. We now report the crystal structure of (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl 4-phenylpiperazin-1-carbodithioate which has potent antimycobacterial activity.

In the title compound (Fig. 1), all bond lengths and angles are within the normal range. The C1—C7/N1/S1 ring system are almost planar, with the mean deviations of 0.039 (2) Å for C6 and −0.052 (1) Å for N1. The dihedral angle between the C1—C7/N1/S1 ring and the phenyl ring is 8.87 (8)°. The N2/N3/C10—C13 ring system has a chair conformation [puckering parameters (Cremer & Pople, 1975): Q = 0.5601 (18) Å, θ = 1.28 (17) ° and φ = 17 (6)°].

The crystal structure is stabilized by weak intermolecular C—H···O interactions (Fig. 1) and weak intramolecular C—H···S interactions (Table 1).

Related literature top

For related literature, see: Ateş et al. (1995); Cao et al. (2005); Çapan et al. (1993); Cremer & Pople (1975); Farghaly & Moharram (1999); Günay et al. (1999); Güzel & Salman (2006); Imamura et al. (2001); Scozzafava et al. (2000); Xu et al. (2002).

Experimental top

The ethanolic solution of 2-(chloromethyl)-1,2-benzisothiazol-3(2H)-on 1,1-dioxide (5 mmol) and potassium 4-phenylpiperazin-1-carbodithioate (5 mmol) were refluxed for 1 h. After evaporation of the solvent in vacuo, products were washed with water and purified by recrystallization from ethanol (Güzel & Salman, 2006).

Yellow powder (62%); mp 445–450 K; IR (KBr): ν 1733 (C═O), 1243 (C═S). 1H-NMR (CDCl3 / 200 MHz): δ 3.15 (t, 4H, J=5.15 Hz, pip. C3,5—H), 4.13 (br s, 4H, pip. C2,6—H), 5.70 (s, 2H, N—CH2—S), 6.69–6.77 (m, 3H, phenyl C3,4,5—H), 7.06–7.14 (m, 2H, phenyl C2,6—H), 7.71–7.81 (m, 3H, bzi. C5,6,7—H), 7.91–7.95 (m, 1H, bzi. C4—H); EIMS: m/z 433 (M+). Analysis calculated for C19H19N3O3S3: C 52.63, H 4.42, N 9.69, S 22.19%. Found: C 53.01, H 4.32, N 9.57, S 22.15%.

Refinement top

All H atoms were positioned geometrically, with C—H = 0.93–0.97Å and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. An ORTEP view of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. View of the weak intermolecular C—H···O hydrogen bonding interactions in the unit cell.
1,1,3-Trioxo-2,3-dihydro-1,2-benzisothiazol-2-ylmethyl 4-phenylpiperazine-1-carbodithioate top
Crystal data top
C19H19N3O3S3Z = 2
Mr = 433.58F(000) = 452
Triclinic, P1Dx = 1.472 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0390 (5) ÅCell parameters from 41005 reflections
b = 11.7619 (7) Åθ = 2.8–27.9°
c = 11.8796 (8) ŵ = 0.41 mm−1
α = 109.029 (5)°T = 296 K
β = 103.791 (5)°Prism, colourless
γ = 102.326 (5)°0.72 × 0.68 × 0.57 mm
V = 978.02 (12) Å3
Data collection top
Stoe IPDS2
diffractometer		3838 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3472 reflections with I > 2σ(I)
plane graphiteRint = 0.042
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.8°
ω scansh = −9→9
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −14→14
Tmin = 0.759, Tmax = 0.802l = −14→14
18676 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0359P)2 + 0.2749P]
where P = (Fo2 + 2Fc2)/3
3838 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C19H19N3O3S3γ = 102.326 (5)°
Mr = 433.58V = 978.02 (12) Å3
Triclinic, P1Z = 2
a = 8.0390 (5) ÅMo Kα radiation
b = 11.7619 (7) ŵ = 0.41 mm−1
c = 11.8796 (8) ÅT = 296 K
α = 109.029 (5)°0.72 × 0.68 × 0.57 mm
β = 103.791 (5)°
Data collection top
Stoe IPDS2
diffractometer		3838 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		3472 reflections with I > 2σ(I)
Tmin = 0.759, Tmax = 0.802Rint = 0.042
18676 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.076Δρmax = 0.38 e Å−3
S = 1.04Δρmin = −0.34 e Å−3
3838 reflectionsAbsolute structure: ?
253 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.29371 (4)0.07783 (3)0.52191 (3)0.0315 (1)
S20.16223 (6)0.36814 (4)0.44690 (4)0.0465 (1)
S30.29352 (7)0.19904 (4)0.26112 (4)0.0552 (2)
O10.16370 (15)−0.03381 (10)0.42204 (10)0.0460 (3)
O20.46502 (14)0.12296 (10)0.51054 (10)0.0410 (3)
O30.13194 (18)0.32432 (11)0.71142 (13)0.0584 (4)
N10.20056 (16)0.19455 (11)0.55194 (12)0.0372 (4)
N20.34280 (18)0.44371 (12)0.31506 (13)0.0455 (4)
N30.32077 (17)0.60864 (12)0.18385 (12)0.0404 (4)
C10.31709 (18)0.07322 (13)0.67057 (13)0.0335 (4)
C20.3811 (2)−0.00962 (15)0.71439 (15)0.0428 (5)
C30.3814 (2)0.00154 (19)0.83429 (17)0.0540 (6)
C40.3238 (3)0.0924 (2)0.90612 (16)0.0590 (6)
C50.2636 (2)0.17575 (17)0.86153 (15)0.0520 (5)
C60.26044 (19)0.16530 (13)0.74175 (13)0.0380 (4)
C70.1914 (2)0.23932 (14)0.67370 (15)0.0405 (4)
C80.0837 (2)0.21508 (15)0.45184 (16)0.0444 (5)
C90.27614 (19)0.34041 (14)0.33358 (14)0.0386 (4)
C100.4363 (2)0.44362 (17)0.22371 (18)0.0514 (6)
C110.3388 (2)0.48396 (16)0.12594 (16)0.0483 (5)
C120.2318 (2)0.61100 (14)0.27846 (15)0.0421 (4)
C130.3282 (2)0.56965 (14)0.37590 (16)0.0474 (5)
C140.25681 (19)0.66404 (14)0.10005 (15)0.0407 (4)
C150.2437 (2)0.61482 (18)−0.02674 (16)0.0531 (5)
C160.1895 (2)0.6746 (2)−0.10496 (18)0.0631 (6)
C170.1431 (2)0.7823 (2)−0.0613 (2)0.0634 (7)
C180.1535 (3)0.83086 (18)0.0631 (2)0.0619 (7)
C190.2096 (2)0.77347 (16)0.14331 (18)0.0522 (6)
H20.42200−0.069900.666000.0510*
H30.42140−0.053600.866800.0650*
H40.325600.097600.986200.0710*
H50.225900.237600.910900.0620*
H8A−0.034500.204200.461400.0530*
H8B0.069200.150300.371500.0530*
H10A0.442200.359200.182600.0620*
H10B0.558900.501300.267100.0620*
H11A0.404700.486000.067700.0580*
H11B0.219700.422300.078100.0580*
H12A0.108000.555200.236800.0500*
H12B0.229300.696300.320100.0500*
H13A0.448000.630300.423700.0570*
H13B0.262300.567600.434200.0570*
H150.271900.54080−0.059100.0640*
H160.184500.64110−0.188700.0760*
H170.105500.82150−0.114600.0760*
H180.122300.903800.094000.0740*
H190.215800.808400.227200.0630*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0363 (2)0.0290 (2)0.0322 (2)0.0115 (1)0.0144 (1)0.0131 (1)
S20.0589 (2)0.0422 (2)0.0546 (2)0.0244 (2)0.0265 (2)0.0284 (2)
S30.0783 (3)0.0425 (2)0.0592 (3)0.0326 (2)0.0289 (2)0.0251 (2)
O10.0512 (6)0.0366 (5)0.0378 (5)0.0078 (5)0.0094 (5)0.0074 (4)
O20.0429 (5)0.0425 (6)0.0495 (6)0.0176 (4)0.0258 (5)0.0229 (5)
O30.0701 (8)0.0444 (6)0.0756 (8)0.0302 (6)0.0432 (7)0.0212 (6)
N10.0429 (6)0.0368 (6)0.0424 (7)0.0192 (5)0.0197 (5)0.0206 (5)
N20.0558 (8)0.0368 (7)0.0522 (8)0.0176 (6)0.0254 (6)0.0207 (6)
N30.0424 (6)0.0386 (6)0.0428 (7)0.0144 (5)0.0173 (5)0.0163 (5)
C10.0330 (6)0.0347 (7)0.0327 (7)0.0072 (5)0.0125 (5)0.0143 (6)
C20.0425 (8)0.0489 (9)0.0465 (8)0.0180 (7)0.0178 (7)0.0262 (7)
C30.0528 (9)0.0714 (12)0.0513 (10)0.0214 (8)0.0178 (8)0.0396 (9)
C40.0634 (11)0.0774 (13)0.0381 (8)0.0157 (9)0.0182 (8)0.0285 (9)
C50.0585 (10)0.0535 (10)0.0390 (8)0.0131 (8)0.0227 (7)0.0107 (7)
C60.0383 (7)0.0352 (7)0.0365 (7)0.0066 (6)0.0150 (6)0.0106 (6)
C70.0416 (7)0.0336 (7)0.0494 (8)0.0117 (6)0.0233 (7)0.0147 (6)
C80.0372 (7)0.0449 (8)0.0566 (9)0.0135 (6)0.0132 (7)0.0284 (7)
C90.0394 (7)0.0386 (7)0.0392 (7)0.0158 (6)0.0079 (6)0.0188 (6)
C100.0565 (9)0.0497 (9)0.0671 (11)0.0260 (8)0.0351 (9)0.0305 (8)
C110.0589 (10)0.0457 (9)0.0528 (9)0.0242 (7)0.0318 (8)0.0207 (7)
C120.0450 (8)0.0343 (7)0.0466 (8)0.0125 (6)0.0196 (7)0.0126 (6)
C130.0628 (10)0.0338 (7)0.0460 (8)0.0124 (7)0.0223 (8)0.0154 (7)
C140.0335 (7)0.0389 (8)0.0449 (8)0.0064 (6)0.0099 (6)0.0163 (6)
C150.0526 (9)0.0563 (10)0.0468 (9)0.0163 (8)0.0135 (7)0.0188 (8)
C160.0539 (10)0.0788 (13)0.0497 (10)0.0104 (9)0.0078 (8)0.0307 (10)
C170.0466 (9)0.0708 (12)0.0734 (13)0.0080 (9)0.0063 (9)0.0460 (11)
C180.0572 (10)0.0500 (10)0.0851 (14)0.0177 (8)0.0212 (10)0.0364 (10)
C190.0573 (10)0.0433 (9)0.0575 (10)0.0163 (7)0.0193 (8)0.0214 (8)
Geometric parameters (Å, °) top
S1—O11.4252 (12)C14—C151.395 (2)
S1—O21.4212 (12)C14—C191.391 (3)
S1—N11.6792 (14)C15—C161.383 (3)
S1—C11.7509 (15)C16—C171.371 (3)
S2—C81.8012 (19)C17—C181.374 (3)
S2—C91.7850 (16)C18—C191.383 (3)
S3—C91.6579 (17)C2—H20.9300
O3—C71.201 (2)C3—H30.9300
N1—C71.395 (2)C4—H40.9300
N1—C81.451 (2)C5—H50.9300
N2—C91.328 (2)C8—H8A0.9700
N2—C101.460 (2)C8—H8B0.9700
N2—C131.465 (2)C10—H10A0.9700
N3—C111.458 (2)C10—H10B0.9700
N3—C121.465 (2)C11—H11A0.9700
N3—C141.415 (2)C11—H11B0.9700
C1—C21.379 (2)C12—H12A0.9700
C1—C61.376 (2)C12—H12B0.9700
C2—C31.387 (2)C13—H13A0.9700
C3—C41.375 (3)C13—H13B0.9700
C4—C51.377 (3)C15—H150.9300
C5—C61.381 (2)C16—H160.9300
C6—C71.473 (2)C17—H170.9300
C10—C111.508 (3)C18—H180.9300
C12—C131.509 (2)C19—H190.9300
S1···O2i3.3476 (13)C15···H12Av3.0300
S2···O33.4010 (15)C15···H11B2.9100
S3···O23.4335 (12)C16···H12Av2.8600
S2···H13B2.3800C17···H3x3.1000
S2···H13Aii3.1400C18···H5vii3.1000
S3···H4iii3.1900C19···H12B2.5300
S3···H8B2.5400H2···S3i3.1100
S3···H10A2.5600H2···O2i2.4300
S3···H18iv3.1700H3···C17ix3.1000
S3···H2i3.1100H4···S3viii3.1900
S3···H17v3.1800H5···O32.8800
O1···C7vi3.000 (2)H5···C11viii2.9500
O1···C6vi3.229 (2)H5···H11Bviii2.4400
O2···C12ii3.276 (2)H5···C18vii3.1000
O2···C2i3.226 (2)H8A···O32.6800
O2···S33.4335 (12)H8A···C2vi2.9600
O2···S1i3.3476 (13)H8B···S32.5400
O2···O2i3.0058 (17)H8B···O12.6400
O2···C13ii3.292 (2)H10A···S32.5600
O3···C12vii3.194 (2)H10B···H13A2.4700
O3···S23.4010 (15)H10B···O3ii2.7600
O1···H19iv2.6400H10B···C7ii3.0200
O1···H8B2.6400H11A···C152.5500
O2···H12Bii2.6900H11A···H152.0000
O2···H13Aii2.6300H11A···H11Axi2.5200
O2···H2i2.4300H11B···C152.9100
O3···H8A2.6800H11B···H5iii2.4400
O3···H15viii2.8200H11B···H12A2.5100
O3···H52.8800H11B···H152.5200
O3···H10Bii2.7600H12A···H11B2.5100
O3···H12Avii2.7000H12A···O3vii2.7000
O3···H12Bvii2.7800H12A···C15v3.0300
N2···N32.866 (2)H12A···C16v2.8600
N3···N22.866 (2)H12B···C192.5300
C2···O2i3.226 (2)H12B···H191.9800
C2···C19ii3.433 (3)H12B···O2ii2.6900
C3···C18ii3.531 (3)H12B···O3vii2.7800
C6···O1vi3.229 (2)H13A···H10B2.4700
C7···O1vi3.000 (2)H13A···S2ii3.1400
C12···O2ii3.276 (2)H13A···O2ii2.6300
C12···O3vii3.194 (2)H13A···C9ii3.0500
C13···O2ii3.292 (2)H13B···S22.3800
C18···C3ii3.531 (3)H15···O3iii2.8200
C19···C2ii3.433 (3)H15···C112.4700
C2···H8Avi2.9600H15···H11A2.0000
C3···H17ix3.0400H15···H11B2.5200
C7···H10Bii3.0200H17···C3x3.0400
C9···H13Aii3.0500H17···S3v3.1800
C11···H152.4700H18···S3xii3.1700
C11···H5iii2.9500H19···O1xii2.6400
C12···H192.6100H19···C122.6100
C15···H11A2.5500H19···H12B1.9800
O1—S1—O2118.56 (7)C14—C19—C18120.80 (18)
O1—S1—N1109.17 (7)C1—C2—H2122.00
O1—S1—C1112.42 (7)C3—C2—H2122.00
O2—S1—N1109.89 (7)C2—C3—H3119.00
O2—S1—C1111.09 (7)C4—C3—H3119.00
N1—S1—C192.61 (7)C3—C4—H4119.00
C8—S2—C9103.70 (8)C5—C4—H4119.00
S1—N1—C7114.08 (11)C4—C5—H5121.00
S1—N1—C8122.14 (11)C6—C5—H5121.00
C7—N1—C8120.29 (14)S2—C8—H8A108.00
C9—N2—C10122.90 (15)S2—C8—H8B109.00
C9—N2—C13126.60 (14)N1—C8—H8A109.00
C10—N2—C13110.45 (14)N1—C8—H8B109.00
C11—N3—C12110.69 (14)H8A—C8—H8B107.00
C11—N3—C14116.06 (13)N2—C10—H10A110.00
C12—N3—C14115.49 (14)N2—C10—H10B110.00
S1—C1—C2126.73 (12)C11—C10—H10A110.00
S1—C1—C6110.55 (11)C11—C10—H10B110.00
C2—C1—C6122.72 (14)H10A—C10—H10B108.00
C1—C2—C3116.60 (16)N3—C11—H11A109.00
C2—C3—C4121.33 (19)N3—C11—H11B109.00
C3—C4—C5121.15 (17)C10—C11—H11A109.00
C4—C5—C6118.40 (16)C10—C11—H11B109.00
C1—C6—C5119.78 (15)H11A—C11—H11B108.00
C1—C6—C7113.08 (13)N3—C12—H12A109.00
C5—C6—C7127.04 (15)N3—C12—H12B109.00
O3—C7—N1122.63 (16)C13—C12—H12A109.00
O3—C7—C6127.78 (15)C13—C12—H12B109.00
N1—C7—C6109.58 (14)H12A—C12—H12B108.00
S2—C8—N1115.09 (12)N2—C13—H13A110.00
S2—C9—S3122.16 (10)N2—C13—H13B110.00
S2—C9—N2112.84 (12)C12—C13—H13A110.00
S3—C9—N2125.00 (13)C12—C13—H13B110.00
N2—C10—C11110.41 (14)H13A—C13—H13B108.00
N3—C11—C10111.57 (14)C14—C15—H15120.00
N3—C12—C13111.54 (14)C16—C15—H15120.00
N2—C13—C12110.59 (14)C15—C16—H16119.00
N3—C14—C15122.15 (16)C17—C16—H16119.00
N3—C14—C19120.46 (15)C16—C17—H17121.00
C15—C14—C19117.36 (17)C18—C17—H17121.00
C14—C15—C16120.92 (18)C17—C18—H18119.00
C15—C16—C17121.19 (18)C19—C18—H18119.00
C16—C17—C18118.4 (2)C14—C19—H19120.00
C17—C18—C19121.3 (2)C18—C19—H19120.00
O1—S1—N1—C7118.00 (12)C11—N3—C14—C15−11.6 (2)
O2—S1—N1—C7−110.39 (12)C11—N3—C12—C1354.79 (18)
C1—S1—N1—C73.17 (13)C14—N3—C12—C13−170.76 (14)
O1—S1—N1—C8−40.93 (15)C12—N3—C14—C1938.5 (2)
O2—S1—N1—C890.68 (14)C12—N3—C14—C15−143.56 (16)
C1—S1—N1—C8−155.76 (13)C11—N3—C14—C19170.48 (16)
O1—S1—C1—C264.79 (17)C2—C1—C6—C5−1.1 (2)
O2—S1—C1—C2−70.73 (16)S1—C1—C6—C5178.41 (13)
N1—S1—C1—C2176.78 (15)S1—C1—C6—C71.70 (18)
O1—S1—C1—C6−114.74 (12)S1—C1—C2—C3−177.70 (14)
O2—S1—C1—C6109.75 (12)C2—C1—C6—C7−177.85 (15)
N1—S1—C1—C6−2.75 (12)C6—C1—C2—C31.8 (3)
C8—S2—C9—S3−0.78 (13)C1—C2—C3—C4−1.2 (3)
C8—S2—C9—N2179.14 (12)C2—C3—C4—C50.0 (3)
C9—S2—C8—N195.71 (13)C3—C4—C5—C60.7 (3)
S1—N1—C7—C6−2.68 (17)C4—C5—C6—C1−0.1 (3)
C8—N1—C7—C6156.68 (14)C4—C5—C6—C7176.08 (18)
S1—N1—C8—S2−119.76 (12)C5—C6—C7—O32.9 (3)
C7—N1—C8—S282.59 (17)C1—C6—C7—N10.5 (2)
S1—N1—C7—O3178.48 (14)C1—C6—C7—O3179.30 (18)
C8—N1—C7—O3−22.2 (3)C5—C6—C7—N1−175.89 (16)
C10—N2—C9—S2−177.89 (13)N2—C10—C11—N357.1 (2)
C13—N2—C9—S2−0.8 (2)N3—C12—C13—N2−55.95 (18)
C10—N2—C9—S32.0 (2)N3—C14—C15—C16−176.66 (17)
C13—N2—C9—S3179.14 (13)C19—C14—C15—C161.4 (3)
C9—N2—C10—C11119.80 (18)N3—C14—C19—C18177.54 (18)
C13—N2—C10—C11−57.72 (19)C15—C14—C19—C18−0.5 (3)
C10—N2—C13—C1257.29 (18)C14—C15—C16—C17−1.5 (3)
C9—N2—C13—C12−120.12 (17)C15—C16—C17—C180.7 (3)
C14—N3—C11—C10170.49 (14)C16—C17—C18—C190.1 (3)
C12—N3—C11—C10−55.34 (18)C17—C18—C19—C14−0.2 (3)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y, z−1; (iv) x, y−1, z; (v) −x, −y+1, −z; (vi) −x, −y, −z+1; (vii) −x, −y+1, −z+1; (viii) x, y, z+1; (ix) x, y−1, z+1; (x) x, y+1, z−1; (xi) −x+1, −y+1, −z; (xii) x, y+1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.433.226 (2)143
C8—H8B···S30.972.543.1134 (18)117
C10—H10A···S30.972.563.075 (2)113
C13—H13B···S20.972.382.9324 (18)116
Symmetry codes: (i) −x+1, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.433.226 (2)143
C8—H8B···S30.972.543.1134 (18)117
C10—H10A···S30.972.563.075 (2)113
C13—H13B···S20.972.382.9324 (18)116
Symmetry codes: (i) −x+1, −y, −z+1.
Acknowledgements top

The authors thank the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Ateş, Ö., Cesur, N., Güner, H., Uzun, M., Kiraz, M. & Kaya, D. (1995). Farmaco, 50, 361–364.

Cao, S.-L., Feng, Y.-P., Jiang, Y.-Y., Liu, S.-Y., Ding, G.-Y. & Li, R.-T. (2005). Bioorg. Med. Chem. Lett. 15, 1915–1917.

Çapan, G., Ergenç, N., Büyüktimkin, S. & Yuluğ, N. (1993). Sci. Pharm. 61, 243–250.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

Farghaly, A. O. & Moharram, A. M. (1999). Boll. Chim. Farm. 138, 280–289.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Günay, N. S., Çapan, G., Ulusoy, N., Ergenç, N., Ötük, G. & Kaya, D. (1999). Farmaco, 54, 826–831.

Güzel, Ö. & Salman, A. (2006). Bioorg. Med. Chem. 14, 7804–7815.

Imamura, H., Ohtake, N., Jona, H., Shimizu, A., Moriya, M., Sato, H., Sugimoto, Y., Ikeura, C., Kiyonaga, H., Nakano, M., Nagano, R., Abe, S., Yamada, K., Hashizume, T. & Morishima, H. (2001). Bioorg. Med. Chem. 9, 1571–1578.

Scozzafava, A., Mastrolorenzo, A. & Supuran, C. T. (2000). Bioorg. Med. Chem. Lett. 10, 1887–1891.

Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.

Xu, L. Z., Jiao, K., Zhang, S. S. & Kuang, S. P. (2002). Bull. Korean Chem. Soc. 23, 1699–1701.