organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 69| Part 9| September 2013| Pages o1401-o1402

Methyl (2Z)-((2Z)-2-{(2E)-[1-(4-methyl­phen­yl)ethyl­­idene]hydrazinyl­­idene}-4-oxo-3-phenyl-1,3-thia­zolidin-5-yl­­idene)ethano­ate

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 19 July 2013; accepted 1 August 2013; online 10 August 2013)

The asymmetric unit of the title compound, C21H19N3O3S, contains two independent mol­ecules. In one mol­ecule, the 1,3-thia­zolidine ring forms dihedral angles of 86.19 (8) and 8.37 (8)° with the phenyl and benzene rings, respectively. The corresponding dihedral angles in the other mol­ecule are 69.60 (7) and 14.08 (7)°. The dihedral angle between the phenyl and benzene rings is 84.70 (8)° in one mol­ecule and 69.62 (8)° in the other. In the crystal, mol­ecules pack in layers approximately parallel to (10-2). There are weak C—H⋯O hydrogen bonds within these layers. Further weak C—H⋯O hydrogen bonding occurs between the layers to form a three-dimensional network. A weak C—H⋯π inter­action is also observed.

Related literature

For the synthesis and general applications of thia­zolidines, see: Pandey et al. (2011[Pandey, Y., Sharma, P. K., Kumar, N. & Singh, A. (2011). Int. J. Pharm. Tech. Res. 3, 980-985.]); Barreca et al. (2002[Barreca, M. L., Balzarini, J., Chimirri, A., Clercq, E. D., Luca, L. D., Höltje, H. D., Höltje, M., Monforte, A. M., Monforte, P., Pannecouque, C., Rao, A. & Zappala, M. (2002). J. Med. Chem. 45, 5410-5413.]); Botti et al. (1996[Botti, P., Pallin, T. D. & Tam, J. P. (1996). J. Am. Chem. Soc. 118, 10018-10024.]); Pfahl et al. (2003[Pfahl, M., Al-Shamma, H. A., Fanjul, A. N., Pleynet, D. P. M., Bao, H., Spruce, L. W., Cow, C. N., Tachdjian, C., Zapt, J. W. & &Wiemann, T. R. (2003). Patent WO 2003/050 098; Int. Appl. No. PCT/US2002/039 178.]); Sayyed et al. (2006[Sayyed, M., Mokle, S., Bokhare, M., Mankar, A., Surwase, S., Bhusare, S. & Vilohute, Y. (2006). Arkivoc, ii, 187-197.]); Sharma et al. (2006[Sharma, R., Nagda, D. P. & Talesara, G. L. (2006). Arkivoc, i, 1-12.]); Babaoğlu et al. (2003[Babaoğlu, K., Page, M. A., Jones, V. C., McNeil, M. R., Dong, C., Naismith, J. H. & Lee, R. E. (2003). Bioorg. Med. Chem. Lett. 13, 3227-3230.]); Çapan et al. (1999[Çapan, G., Ulusoy, N., Ergenç, N. & Kiraz, M. (1999). Monatsh. Chem. 130, 1399-1407.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C21H19N3O3S

  • Mr = 393.46

  • Monoclinic, P 21 /c

  • a = 8.3713 (12) Å

  • b = 21.568 (3) Å

  • c = 21.591 (3) Å

  • β = 96.411 (2)°

  • V = 3873.9 (9) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 150 K

  • 0.19 × 0.19 × 0.11 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.81, Tmax = 0.98

  • 69242 measured reflections

  • 9850 independent reflections

  • 7890 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.112

  • S = 1.05

  • 9850 reflections

  • 511 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C36–C41 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯O6i 0.95 2.56 3.4802 (19) 163
C6—H6B⋯O4i 0.98 2.52 3.465 (2) 163
C8—H8⋯O2ii 0.95 2.56 3.359 (2) 142
C12—H12⋯O4 0.95 2.43 3.302 (2) 152
C27—H27B⋯O1i 0.98 2.45 3.410 (2) 166
C30—H30⋯O5iii 0.95 2.44 3.331 (2) 157
C32—H32⋯O1iv 0.95 2.57 3.340 (2) 139
C33—H33⋯Cgv 0.95 2.58 3.4951 (19) 162
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z+1; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (v) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]).; software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Heterocyclic compounds such as thiazolidines have demonstrated widespread applications as pharmaceuticals (Pandey et al., 2011; Barreca et al., 2002) and materials (Botti et al., 1996). Thiazolidinone derivatives exhibit anticancer properties (Pfahl et al., 2003) as well as antibacterial (Sayyed et al., 2006), antimycobacterial (Babaoğlu et al., 2003), antimicrobial (Sharma et al., 2006) and antifungal (Çapan et al., 1999) activities. Therefore, we have synthesized the title compound (I) and determined its crystal structure.

The asymmetric unit of (I) is shown in Fig. 1. In one molecule, the 1,3-thiazolidine ring (S1/N1/C1–C3) forms dihedral angles of 86.19 (8) and 8.37 (8) °, respectively, with the phenyl ring (C7–C12) and the benzene ring (C15–C20). In the other molecule the corresponding angles between (S2/N4/C22-C24) are 69.60 (7) (C28-C33) and 14.08 (7)° (C36-C41), respectively. The dihedral angle between the phenyl and benzene rings is 84.70 (8)° (C7-C12 and C15-C20) and 69.62 (8)° (C28-C33 and C26-C41). The differences in the dihedral angles may be due to the packing effects of neighbouring molecules. The bond lengths (Allen et al., 1987) and angles in each molecule are normal.

In the crystal, molecules are arranged in layers approximately parallel to (102) connected by weak C—H···O hydrogen bonds (Table 1, Fig. 2). Additional weak C—H···O hydrogen bonds occur between theses layers (Table 1, Fig. 2) forming a three-dimensional network. A weak intermolecular C—H···π interaction is also observed (Table 1).

Related literature top

For the synthesis and general applications of thiazolidines see: Pandey et al. (2011); Barreca et al. (2002); Botti et al. (1996); Pfahl et al. (2003); Sayyed et al. (2006); Sharma et al. (2006); Babaoğlu et al. (2003); Çapan et al. (1999). For standard bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 283 mg (1 mmol) (2E)-2-[1-(4-methylphenyl)ethylidene]-N-phenylhydrazinecarbothioamide and 142 mg (1 mmol) of dimethyl but-2-ynedioate in 50 ml methanol was refluxed for three hours. The excess solvent was evaporated under vacuum and the residual solid product was collected and recrystallized from ethanol to afford a clear yellow blocks (M.p. 527 – 529 K) suitable for X-ray diffraction.

Refinement top

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.95 (aromatic H) and 0.98 Å (methyl H), with Uiso(H) = 1.2 Uiso(C) for aromatic H atoms and Uiso(H) = 1.5 Uiso(C) for methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2012).; software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) showing a weak C—H···O hydrogen bond (dashed line) between the independent molecules. Displacement ellipsoids are at the 30% probabilty level.
[Figure 2] Fig. 2. Part of the crystal structure viewed approximately along the b axis with weak C—H···O hydrogen bonds shown as dashed lines.
[Figure 3] Fig. 3. A view along the b axis showing weak C—H···π interactions as dashed lines.
Methyl (2Z)-((2Z)-2-{(2E)-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)ethanoate top
Crystal data top
C21H19N3O3SF(000) = 1648
Mr = 393.46Dx = 1.349 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9179 reflections
a = 8.3713 (12) Åθ = 2.5–28.6°
b = 21.568 (3) ŵ = 0.19 mm1
c = 21.591 (3) ÅT = 150 K
β = 96.411 (2)°Block, clear yellow
V = 3873.9 (9) Å30.19 × 0.19 × 0.11 mm
Z = 8
Data collection top
Bruker SMART APEX CCD
diffractometer
9850 independent reflections
Radiation source: fine-focus sealed tube7890 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 8.3660 pixels mm-1θmax = 28.6°, θmin = 1.9°
ϕ and ω scansh = 1011
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 2828
Tmin = 0.81, Tmax = 0.98l = 2828
69242 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.112 W = 1/[Σ2(FO2) + (0.0511P)2 + 1.054P] WHERE P = (FO2 + 2FC2)/3
S = 1.05(Δ/σ)max = 0.001
9850 reflectionsΔρmax = 0.34 e Å3
511 parametersΔρmin = 0.34 e Å3
Crystal data top
C21H19N3O3SV = 3873.9 (9) Å3
Mr = 393.46Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.3713 (12) ŵ = 0.19 mm1
b = 21.568 (3) ÅT = 150 K
c = 21.591 (3) Å0.19 × 0.19 × 0.11 mm
β = 96.411 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
9850 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
7890 reflections with I > 2σ(I)
Tmin = 0.81, Tmax = 0.98Rint = 0.057
69242 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.05Δρmax = 0.34 e Å3
9850 reflectionsΔρmin = 0.34 e Å3
511 parameters
Special details top

Experimental. 1H-NMR [δ, p.p.m., CDCl3]: 2.27 (S, 3H, CH3), 2.39 (S, 3H, CH3), 3.88 (S, 3H, OCH3), 6.97 (S, 1H, vinyl - CH), 7.19–7.26 (m, 2H, Ar- H), 7.44–7.47 (m, 3H, Ar - H), 7.51–7.55 (m, 2H, Ar - H), 7.78–7.83 (m, 2H, Ar - H). 13C-NMR [δ, p.p.m., CDCl3]: 15.03 (CH3), 21.42 (CH3), 52.49 (OCH3), 115.98 (vinyl-CH), 126.92, 127.46, 128.90, 129.09, 129.30 (Ar - CH), 132.21, 133.76 (Ar - C), 140.75 (Ar – C– N), 142.05 (CH3 – C=N), 158.15 (thiazole – C.2), 164.9 (cyclic – C=O), 166.59 (ester - CO).

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
S10.59531 (4)0.00119 (2)0.42718 (2)0.0226 (1)
O10.79183 (14)0.14802 (5)0.50471 (5)0.0337 (3)
O20.74230 (14)0.08842 (5)0.50854 (5)0.0302 (3)
O30.93261 (13)0.06779 (5)0.58848 (5)0.0285 (3)
N10.60347 (15)0.12318 (6)0.42279 (6)0.0241 (3)
N20.42172 (15)0.07810 (6)0.34568 (6)0.0263 (4)
N30.36391 (15)0.01878 (6)0.32675 (6)0.0260 (4)
C10.52809 (17)0.07228 (7)0.39283 (7)0.0228 (4)
C20.71496 (18)0.10956 (7)0.47312 (7)0.0250 (4)
C30.72573 (17)0.04065 (6)0.48243 (7)0.0227 (4)
C40.82274 (18)0.01562 (7)0.52956 (7)0.0247 (4)
C50.82622 (18)0.05181 (7)0.53990 (7)0.0244 (4)
C60.9370 (2)0.13330 (7)0.60373 (8)0.0319 (5)
C70.55457 (18)0.18631 (6)0.40694 (7)0.0244 (4)
C80.4378 (2)0.21376 (7)0.43831 (8)0.0306 (5)
C90.3904 (2)0.27400 (8)0.42290 (9)0.0368 (5)
C100.4589 (2)0.30597 (7)0.37721 (8)0.0367 (5)
C110.5760 (2)0.27798 (8)0.34637 (8)0.0389 (6)
C120.6251 (2)0.21778 (8)0.36116 (8)0.0334 (5)
C130.25712 (18)0.01879 (7)0.27854 (7)0.0260 (4)
C140.1978 (2)0.07602 (8)0.24368 (8)0.0346 (5)
C150.19100 (18)0.04256 (8)0.25778 (7)0.0279 (4)
C160.2319 (2)0.09620 (8)0.29201 (8)0.0367 (5)
C170.1656 (2)0.15299 (8)0.27352 (9)0.0408 (6)
C180.0564 (2)0.15848 (9)0.22020 (9)0.0390 (6)
C190.0179 (2)0.10561 (9)0.18561 (9)0.0436 (6)
C200.0840 (2)0.04854 (9)0.20358 (8)0.0373 (5)
C210.0198 (3)0.22033 (10)0.20217 (11)0.0575 (8)
S20.57525 (4)0.01716 (2)0.19020 (2)0.0234 (1)
O40.79280 (13)0.12820 (5)0.26255 (5)0.0291 (3)
O50.70484 (14)0.10494 (5)0.27998 (5)0.0326 (3)
O60.89186 (13)0.08142 (5)0.36026 (5)0.0286 (3)
N40.60388 (15)0.10390 (5)0.18031 (6)0.0229 (3)
N50.42977 (16)0.06042 (6)0.10082 (6)0.0266 (4)
N60.35687 (16)0.00405 (6)0.08093 (6)0.0266 (4)
C220.52529 (17)0.05328 (6)0.15065 (7)0.0230 (4)
C230.70949 (17)0.09035 (6)0.23226 (7)0.0222 (4)
C240.70620 (17)0.02231 (6)0.24547 (7)0.0221 (4)
C250.79655 (17)0.00146 (6)0.29468 (7)0.0230 (4)
C260.79111 (18)0.06797 (7)0.30954 (7)0.0239 (4)
C270.8927 (2)0.14517 (7)0.38080 (8)0.0350 (5)
C280.57567 (17)0.16650 (6)0.15832 (7)0.0244 (4)
C290.49625 (19)0.20722 (7)0.19350 (8)0.0313 (5)
C300.4714 (2)0.26784 (8)0.17250 (9)0.0401 (6)
C310.5262 (2)0.28624 (8)0.11736 (9)0.0429 (6)
C320.6065 (2)0.24503 (8)0.08284 (9)0.0415 (6)
C330.6307 (2)0.18437 (7)0.10301 (8)0.0329 (5)
C340.28762 (18)0.00516 (7)0.02447 (7)0.0246 (4)
C350.2913 (2)0.05937 (7)0.01919 (7)0.0321 (5)
C360.19741 (18)0.05168 (7)0.00294 (7)0.0257 (4)
C370.2025 (2)0.10475 (7)0.03991 (8)0.0310 (5)
C380.1130 (2)0.15691 (8)0.02074 (8)0.0358 (5)
C390.0141 (2)0.15761 (8)0.03558 (8)0.0360 (5)
C400.0101 (2)0.10492 (8)0.07239 (9)0.0404 (5)
C410.1002 (2)0.05263 (8)0.05402 (8)0.0343 (5)
C420.0846 (3)0.21374 (10)0.05661 (11)0.0567 (8)
H40.890000.041800.556600.0300*
H6A0.832300.146100.615500.0480*
H6B1.020200.140800.638600.0480*
H6C0.961600.157200.567400.0480*
H80.390800.191800.469800.0370*
H90.310100.293400.444000.0440*
H100.425700.347200.366900.0440*
H110.623000.300100.314900.0470*
H120.705900.198500.340200.0400*
H14A0.245300.112800.265200.0520*
H14B0.080400.078200.241800.0520*
H14C0.228900.074500.201300.0520*
H160.306300.093700.328500.0440*
H170.195200.188900.297600.0490*
H190.055200.108400.148800.0520*
H200.056100.013000.178700.0450*
H21A0.129600.221300.213900.0860*
H21B0.043500.253600.223900.0860*
H21C0.022700.226200.157000.0860*
H250.865600.025100.320600.0280*
H27A0.796200.153300.401400.0530*
H27B0.988600.152800.410200.0530*
H27C0.893800.172700.344800.0530*
H290.459200.194100.231400.0380*
H300.416800.296500.196100.0480*
H310.508600.327600.103100.0510*
H320.645100.258300.045300.0500*
H330.684200.155600.079200.0400*
H35A0.358100.092400.001300.0480*
H35B0.181800.074900.030200.0480*
H35C0.336500.046200.057000.0480*
H370.268000.105300.078800.0370*
H380.119300.192700.046500.0430*
H400.055900.104500.111200.0480*
H410.095700.017300.080400.0410*
H42A0.198500.202300.063100.0850*
H42B0.068600.246100.024700.0850*
H42C0.050800.229300.095800.0850*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0235 (2)0.0238 (2)0.0199 (2)0.0006 (1)0.0002 (1)0.0011 (1)
O10.0348 (6)0.0278 (6)0.0350 (6)0.0002 (5)0.0117 (5)0.0044 (5)
O20.0365 (6)0.0277 (5)0.0250 (5)0.0039 (4)0.0030 (5)0.0016 (4)
O30.0288 (6)0.0262 (5)0.0286 (6)0.0011 (4)0.0055 (4)0.0035 (4)
N10.0253 (6)0.0225 (6)0.0230 (6)0.0015 (5)0.0033 (5)0.0004 (5)
N20.0260 (7)0.0280 (6)0.0239 (6)0.0021 (5)0.0021 (5)0.0034 (5)
N30.0259 (7)0.0287 (6)0.0224 (6)0.0013 (5)0.0022 (5)0.0040 (5)
C10.0225 (7)0.0253 (7)0.0203 (7)0.0018 (5)0.0012 (5)0.0021 (5)
C20.0244 (7)0.0257 (7)0.0241 (7)0.0016 (5)0.0005 (6)0.0020 (6)
C30.0209 (7)0.0244 (7)0.0229 (7)0.0003 (5)0.0031 (6)0.0014 (5)
C40.0227 (7)0.0268 (7)0.0240 (7)0.0003 (5)0.0006 (6)0.0012 (6)
C50.0217 (7)0.0288 (7)0.0228 (7)0.0004 (5)0.0024 (6)0.0006 (6)
C60.0347 (9)0.0277 (8)0.0318 (8)0.0031 (6)0.0025 (7)0.0054 (6)
C70.0268 (8)0.0212 (7)0.0235 (7)0.0003 (5)0.0048 (6)0.0017 (5)
C80.0328 (9)0.0275 (7)0.0320 (8)0.0003 (6)0.0056 (7)0.0009 (6)
C90.0357 (9)0.0275 (8)0.0477 (10)0.0042 (6)0.0068 (8)0.0027 (7)
C100.0419 (10)0.0241 (7)0.0417 (10)0.0013 (7)0.0053 (8)0.0029 (7)
C110.0494 (11)0.0340 (9)0.0335 (9)0.0030 (7)0.0052 (8)0.0083 (7)
C120.0386 (9)0.0335 (8)0.0288 (8)0.0021 (7)0.0063 (7)0.0011 (6)
C130.0202 (7)0.0371 (8)0.0203 (7)0.0019 (6)0.0012 (6)0.0025 (6)
C140.0290 (9)0.0438 (9)0.0292 (8)0.0007 (7)0.0052 (7)0.0053 (7)
C150.0202 (7)0.0394 (8)0.0237 (7)0.0007 (6)0.0009 (6)0.0057 (6)
C160.0290 (9)0.0410 (9)0.0373 (9)0.0027 (7)0.0090 (7)0.0070 (7)
C170.0321 (9)0.0367 (9)0.0505 (11)0.0038 (7)0.0087 (8)0.0081 (8)
C180.0266 (9)0.0456 (10)0.0437 (10)0.0008 (7)0.0006 (7)0.0190 (8)
C190.0362 (10)0.0593 (12)0.0323 (9)0.0035 (8)0.0091 (8)0.0150 (8)
C200.0338 (9)0.0501 (10)0.0260 (8)0.0007 (7)0.0061 (7)0.0025 (7)
C210.0447 (12)0.0523 (12)0.0720 (15)0.0036 (9)0.0093 (11)0.0260 (11)
S20.0273 (2)0.0195 (2)0.0226 (2)0.0013 (1)0.0010 (1)0.0012 (1)
O40.0307 (6)0.0212 (5)0.0330 (6)0.0013 (4)0.0072 (5)0.0031 (4)
O50.0379 (7)0.0259 (5)0.0317 (6)0.0070 (5)0.0066 (5)0.0031 (4)
O60.0309 (6)0.0226 (5)0.0301 (6)0.0011 (4)0.0060 (5)0.0046 (4)
N40.0250 (6)0.0187 (5)0.0240 (6)0.0015 (4)0.0021 (5)0.0007 (4)
N50.0292 (7)0.0230 (6)0.0261 (6)0.0001 (5)0.0032 (5)0.0021 (5)
N60.0297 (7)0.0224 (6)0.0257 (6)0.0007 (5)0.0054 (5)0.0019 (5)
C220.0227 (7)0.0213 (6)0.0244 (7)0.0007 (5)0.0005 (6)0.0026 (5)
C230.0218 (7)0.0207 (6)0.0237 (7)0.0016 (5)0.0012 (5)0.0020 (5)
C240.0227 (7)0.0197 (6)0.0242 (7)0.0003 (5)0.0042 (6)0.0025 (5)
C250.0231 (7)0.0222 (7)0.0232 (7)0.0019 (5)0.0009 (6)0.0016 (5)
C260.0244 (7)0.0238 (7)0.0231 (7)0.0000 (5)0.0016 (6)0.0024 (5)
C270.0426 (10)0.0242 (7)0.0352 (9)0.0027 (6)0.0092 (7)0.0092 (6)
C280.0225 (7)0.0197 (6)0.0292 (8)0.0011 (5)0.0048 (6)0.0001 (5)
C290.0295 (8)0.0274 (7)0.0354 (9)0.0036 (6)0.0032 (7)0.0042 (6)
C300.0388 (10)0.0264 (8)0.0513 (11)0.0094 (7)0.0116 (8)0.0097 (7)
C310.0444 (11)0.0224 (8)0.0560 (12)0.0003 (7)0.0201 (9)0.0070 (7)
C320.0421 (10)0.0363 (9)0.0437 (10)0.0055 (7)0.0057 (8)0.0135 (8)
C330.0345 (9)0.0301 (8)0.0338 (9)0.0013 (6)0.0021 (7)0.0037 (6)
C340.0225 (7)0.0256 (7)0.0245 (7)0.0048 (5)0.0021 (6)0.0016 (5)
C350.0388 (9)0.0296 (8)0.0265 (8)0.0016 (6)0.0020 (7)0.0011 (6)
C360.0250 (7)0.0260 (7)0.0245 (7)0.0047 (5)0.0042 (6)0.0041 (6)
C370.0357 (9)0.0292 (8)0.0262 (8)0.0001 (6)0.0049 (7)0.0027 (6)
C380.0444 (10)0.0290 (8)0.0332 (9)0.0025 (7)0.0015 (7)0.0020 (7)
C390.0358 (9)0.0330 (8)0.0379 (9)0.0004 (7)0.0014 (7)0.0134 (7)
C400.0418 (10)0.0393 (9)0.0352 (9)0.0051 (7)0.0168 (8)0.0120 (7)
C410.0404 (10)0.0305 (8)0.0286 (8)0.0068 (7)0.0105 (7)0.0020 (6)
C420.0638 (14)0.0453 (11)0.0589 (14)0.0164 (10)0.0026 (11)0.0202 (10)
Geometric parameters (Å, º) top
S1—C11.7676 (16)C11—H110.9500
S1—C31.7460 (15)C12—H120.9500
S2—C221.7699 (14)C14—H14A0.9800
S2—C241.7488 (15)C14—H14B0.9800
O1—C21.2122 (19)C14—H14C0.9800
O2—C51.2121 (19)C16—H160.9500
O3—C51.3430 (19)C17—H170.9500
O3—C61.4503 (19)C19—H190.9500
O4—C231.2160 (18)C20—H200.9500
O5—C261.2090 (19)C21—H21B0.9800
O6—C261.3373 (19)C21—H21C0.9800
O6—C271.4445 (19)C21—H21A0.9800
N1—C71.4517 (19)C23—C241.4958 (19)
N1—C11.390 (2)C24—C251.336 (2)
N1—C21.383 (2)C25—C261.472 (2)
N2—C11.282 (2)C28—C291.380 (2)
N2—N31.4121 (18)C28—C331.382 (2)
N3—C131.294 (2)C29—C301.392 (2)
N4—C221.3931 (18)C30—C311.381 (3)
N4—C281.4419 (17)C31—C321.382 (3)
N4—C231.380 (2)C32—C331.387 (2)
N5—C221.276 (2)C34—C351.504 (2)
N5—N61.4059 (19)C34—C361.487 (2)
N6—C341.290 (2)C36—C371.393 (2)
C2—C31.501 (2)C36—C411.397 (2)
C3—C41.342 (2)C37—C381.389 (2)
C4—C51.471 (2)C38—C391.393 (2)
C7—C121.384 (2)C39—C401.385 (2)
C7—C81.383 (2)C39—C421.507 (3)
C8—C91.388 (2)C40—C411.390 (2)
C9—C101.380 (2)C25—H250.9500
C10—C111.384 (2)C27—H27A0.9800
C11—C121.388 (2)C27—H27B0.9800
C13—C141.501 (2)C27—H27C0.9800
C13—C151.484 (2)C29—H290.9500
C15—C161.395 (2)C30—H300.9500
C15—C201.398 (2)C31—H310.9500
C16—C171.385 (2)C32—H320.9500
C17—C181.393 (3)C33—H330.9500
C18—C211.511 (3)C35—H35A0.9800
C18—C191.381 (3)C35—H35B0.9800
C19—C201.387 (3)C35—H35C0.9800
C4—H40.9500C37—H370.9500
C6—H6B0.9800C38—H380.9500
C6—H6C0.9800C40—H400.9500
C6—H6A0.9800C41—H410.9500
C8—H80.9500C42—H42A0.9800
C9—H90.9500C42—H42B0.9800
C10—H100.9500C42—H42C0.9800
C1—S1—C390.54 (7)C19—C20—H20120.00
C22—S2—C2490.44 (7)C18—C21—H21A109.00
C5—O3—C6115.16 (12)C18—C21—H21B109.00
C26—O6—C27116.03 (12)C18—C21—H21C109.00
C2—N1—C7122.17 (13)H21A—C21—H21B109.00
C1—N1—C7122.00 (12)H21A—C21—H21C110.00
C1—N1—C2115.45 (13)H21B—C21—H21C109.00
N3—N2—C1109.05 (12)S2—C22—N4112.14 (10)
N2—N3—C13114.60 (13)S2—C22—N5127.04 (11)
C22—N4—C23115.76 (11)N4—C22—N5120.82 (13)
C23—N4—C28122.18 (11)O4—C23—N4124.89 (12)
C22—N4—C28122.07 (12)O4—C23—C24125.29 (13)
N6—N5—C22111.28 (12)N4—C23—C24109.82 (12)
N5—N6—C34113.98 (13)S2—C24—C23111.77 (10)
S1—C1—N2125.36 (12)S2—C24—C25127.74 (11)
S1—C1—N1112.54 (11)C23—C24—C25120.49 (13)
N1—C1—N2122.11 (14)C24—C25—C26121.26 (13)
O1—C2—N1124.49 (14)O5—C26—O6125.04 (14)
O1—C2—C3125.59 (14)O5—C26—C25123.98 (14)
N1—C2—C3109.92 (13)O6—C26—C25110.97 (13)
S1—C3—C2111.56 (10)N4—C28—C29119.09 (13)
S1—C3—C4126.95 (11)N4—C28—C33119.18 (13)
C2—C3—C4121.46 (13)C29—C28—C33121.73 (13)
C3—C4—C5120.84 (13)C28—C29—C30118.84 (15)
O2—C5—O3124.16 (14)C29—C30—C31119.92 (16)
O2—C5—C4123.97 (14)C30—C31—C32120.57 (16)
O3—C5—C4111.86 (13)C31—C32—C33120.02 (17)
N1—C7—C12119.78 (13)C28—C33—C32118.91 (15)
C8—C7—C12121.39 (14)N6—C34—C35124.61 (14)
N1—C7—C8118.83 (13)N6—C34—C36116.04 (13)
C7—C8—C9118.82 (15)C35—C34—C36119.35 (13)
C8—C9—C10120.57 (16)C34—C36—C37121.08 (14)
C9—C10—C11119.96 (15)C34—C36—C41120.86 (14)
C10—C11—C12120.32 (16)C37—C36—C41118.02 (14)
C7—C12—C11118.94 (15)C36—C37—C38120.91 (15)
N3—C13—C14124.30 (14)C37—C38—C39121.15 (16)
N3—C13—C15116.33 (13)C38—C39—C40117.78 (16)
C14—C13—C15119.36 (13)C38—C39—C42121.62 (16)
C13—C15—C16121.22 (14)C40—C39—C42120.60 (17)
C13—C15—C20121.17 (15)C39—C40—C41121.64 (17)
C16—C15—C20117.61 (16)C36—C41—C40120.49 (16)
C15—C16—C17120.94 (16)C24—C25—H25119.00
C16—C17—C18121.22 (17)C26—C25—H25119.00
C19—C18—C21121.55 (17)O6—C27—H27A109.00
C17—C18—C19117.95 (17)O6—C27—H27B110.00
C17—C18—C21120.48 (18)O6—C27—H27C109.00
C18—C19—C20121.31 (17)H27A—C27—H27B109.00
C15—C20—C19120.95 (17)H27A—C27—H27C109.00
C3—C4—H4120.00H27B—C27—H27C109.00
C5—C4—H4120.00C28—C29—H29121.00
O3—C6—H6A109.00C30—C29—H29121.00
O3—C6—H6B109.00C29—C30—H30120.00
O3—C6—H6C109.00C31—C30—H30120.00
H6A—C6—H6B110.00C30—C31—H31120.00
H6A—C6—H6C109.00C32—C31—H31120.00
H6B—C6—H6C109.00C31—C32—H32120.00
C7—C8—H8121.00C33—C32—H32120.00
C9—C8—H8121.00C28—C33—H33121.00
C10—C9—H9120.00C32—C33—H33121.00
C8—C9—H9120.00C34—C35—H35A109.00
C9—C10—H10120.00C34—C35—H35B109.00
C11—C10—H10120.00C34—C35—H35C109.00
C12—C11—H11120.00H35A—C35—H35B109.00
C10—C11—H11120.00H35A—C35—H35C109.00
C7—C12—H12121.00H35B—C35—H35C110.00
C11—C12—H12121.00C36—C37—H37120.00
C13—C14—H14A109.00C38—C37—H37119.00
C13—C14—H14B110.00C37—C38—H38119.00
C13—C14—H14C109.00C39—C38—H38119.00
H14A—C14—H14B109.00C39—C40—H40119.00
H14A—C14—H14C109.00C41—C40—H40119.00
H14B—C14—H14C109.00C36—C41—H41120.00
C17—C16—H16120.00C40—C41—H41120.00
C15—C16—H16119.00C39—C42—H42A109.00
C16—C17—H17119.00C39—C42—H42B109.00
C18—C17—H17119.00C39—C42—H42C109.00
C20—C19—H19119.00H42A—C42—H42B110.00
C18—C19—H19119.00H42A—C42—H42C109.00
C15—C20—H20120.00H42B—C42—H42C109.00
C3—S1—C1—N10.11 (11)C3—C4—C5—O3178.91 (14)
C3—S1—C1—N2179.71 (14)N1—C7—C8—C9179.64 (15)
C1—S1—C3—C20.07 (11)C12—C7—C8—C90.5 (2)
C1—S1—C3—C4177.97 (15)N1—C7—C12—C11179.59 (14)
C24—S2—C22—N41.44 (11)C8—C7—C12—C110.5 (2)
C24—S2—C22—N5178.62 (15)C7—C8—C9—C100.2 (3)
C22—S2—C24—C230.07 (10)C8—C9—C10—C110.1 (3)
C22—S2—C24—C25179.95 (14)C9—C10—C11—C120.0 (3)
C6—O3—C5—C4176.87 (12)C10—C11—C12—C70.3 (3)
C6—O3—C5—O22.7 (2)N3—C13—C15—C165.6 (2)
C27—O6—C26—C25177.82 (12)C14—C13—C15—C205.1 (2)
C27—O6—C26—O51.2 (2)N3—C13—C15—C20175.20 (15)
C2—N1—C1—S10.13 (16)C14—C13—C15—C16174.20 (15)
C7—N1—C2—C3173.02 (13)C13—C15—C20—C19177.58 (15)
C1—N1—C7—C890.13 (18)C13—C15—C16—C17177.81 (15)
C1—N1—C7—C1289.96 (18)C16—C15—C20—C191.7 (2)
C2—N1—C7—C882.35 (19)C20—C15—C16—C171.5 (2)
C2—N1—C7—C1297.56 (18)C15—C16—C17—C180.1 (3)
C1—N1—C2—O1179.89 (15)C16—C17—C18—C191.0 (3)
C1—N1—C2—C30.08 (17)C16—C17—C18—C21177.52 (18)
C7—N1—C2—O17.0 (2)C21—C18—C19—C20177.73 (18)
C7—N1—C1—N26.8 (2)C17—C18—C19—C200.8 (3)
C2—N1—C1—N2179.70 (14)C18—C19—C20—C150.6 (3)
C7—N1—C1—S1173.08 (11)O4—C23—C24—S2178.30 (12)
N3—N2—C1—N1178.21 (13)O4—C23—C24—C251.7 (2)
C1—N2—N3—C13178.90 (13)N4—C23—C24—S21.55 (15)
N3—N2—C1—S11.60 (18)N4—C23—C24—C25178.47 (14)
N2—N3—C13—C140.8 (2)S2—C24—C25—C262.0 (2)
N2—N3—C13—C15178.93 (12)C23—C24—C25—C26178.07 (13)
C23—N4—C22—N5177.30 (14)C24—C25—C26—O51.4 (2)
C28—N4—C22—S2176.83 (11)C24—C25—C26—O6179.53 (14)
C23—N4—C22—S22.75 (16)N4—C28—C29—C30179.08 (14)
C22—N4—C23—O4177.12 (14)C33—C28—C29—C300.1 (2)
C22—N4—C23—C242.73 (17)N4—C28—C33—C32178.52 (14)
C28—N4—C23—O43.3 (2)C29—C28—C33—C320.6 (2)
C28—N4—C23—C24176.84 (12)C28—C29—C30—C310.1 (2)
C22—N4—C28—C29110.72 (17)C29—C30—C31—C320.3 (3)
C22—N4—C28—C3370.12 (19)C30—C31—C32—C330.9 (3)
C28—N4—C22—N53.1 (2)C31—C32—C33—C281.0 (3)
C23—N4—C28—C33110.33 (17)N6—C34—C36—C376.3 (2)
C23—N4—C28—C2968.83 (19)N6—C34—C36—C41171.27 (15)
N6—N5—C22—S23.38 (19)C35—C34—C36—C37174.39 (15)
N6—N5—C22—N4176.57 (13)C35—C34—C36—C418.0 (2)
C22—N5—N6—C34165.53 (14)C34—C36—C37—C38177.40 (15)
N5—N6—C34—C36175.22 (13)C41—C36—C37—C380.3 (2)
N5—N6—C34—C354.0 (2)C34—C36—C41—C40176.81 (15)
O1—C2—C3—C41.8 (2)C37—C36—C41—C400.9 (2)
O1—C2—C3—S1179.97 (14)C36—C37—C38—C390.7 (3)
N1—C2—C3—S10.02 (16)C37—C38—C39—C401.1 (3)
N1—C2—C3—C4178.15 (14)C37—C38—C39—C42179.48 (18)
C2—C3—C4—C5177.02 (14)C38—C39—C40—C410.5 (3)
S1—C3—C4—C50.8 (2)C42—C39—C40—C41179.92 (18)
C3—C4—C5—O21.5 (2)C39—C40—C41—C360.5 (3)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C36–C41 ring.
D—H···AD—HH···AD···AD—H···A
C4—H4···O6i0.952.563.4802 (19)163
C6—H6B···O4i0.982.523.465 (2)163
C8—H8···O2ii0.952.563.359 (2)142
C12—H12···O40.952.433.302 (2)152
C14—H14A···N20.982.282.728 (2)107
C27—H27B···O1i0.982.453.410 (2)166
C30—H30···O5iii0.952.443.331 (2)157
C32—H32···O1iv0.952.573.340 (2)139
C35—H35A···N50.982.272.718 (2)106
C33—H33···Cgv0.952.583.4951 (19)162
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+1; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z1/2; (v) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C36–C41 ring.
D—H···AD—HH···AD···AD—H···A
C4—H4···O6i0.952.563.4802 (19)163
C6—H6B···O4i0.982.523.465 (2)163
C8—H8···O2ii0.952.563.359 (2)142
C12—H12···O40.952.433.302 (2)152
C27—H27B···O1i0.982.453.410 (2)166
C30—H30···O5iii0.952.443.331 (2)157
C32—H32···O1iv0.952.573.340 (2)139
C33—H33···Cgv0.952.583.4951 (19)162
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+1; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z1/2; (v) x+1, y, z.
 

Acknowledgements

The use of X-ray crystallographic facilities at Tulane University, USA, is gratefully acknowledged, We thank Manchester Metropolitan University, Erciyes University and Minia University for supporting this study.

References

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Volume 69| Part 9| September 2013| Pages o1401-o1402
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