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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 9| September 2013| Pages o1408-o1409

(4E)-4-[(2-Hy­dr­oxy­anilino)methyl­­idene]-1-phenyl­pyrazolidine-3,5-dione di­methyl sulfoxide hemisolvate

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, dDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada E-18071, Spain, eDepartment of Chemistry, Sohag University, 82524 Sohag, Egypt, fDepartment of Chemistry, University of Leicester, Leicester, England, and gKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 6 August 2013; accepted 7 August 2013; online 10 August 2013)

The asymmetric unit of the title compound, C16H13N3O3·0.5C2H6OS, is composed of two independent pyrazolidine-3,5-dione mol­ecules and one dimethyl sulfoxide solvent mol­ecule. In each pyrazolidine-3,5-dione mol­ecule, an intra­molecular N—H⋯O hydrogen bond forms an S(5)S(6) motif. In the crystal, pairs of each independent pyrazolidine-3,5-dione mol­ecule are linked by N—H⋯O hydrogen bonds, forming dimers with R22(8) motifs. These dimers are connected with the other mol­ecules through the solvent mol­ecules via O—H⋯O hydrogen bonds, forming ribbons along the b-axis direction. C—H⋯π inter­actions connect the ribbons. C—H⋯O interactions also occur.

Related literature

For the significant role of pyrazolidinediones in the synthesis of various heterocyclic compounds, see: Elnagdy & Ohta (1973[Elnagdy, M. H. & Ohta, M. (1973). Bull. Chem. Soc. Jpn, 46, 1830-1833.]); Abdel-Rahman et al. (2004[Abdel-Rahman, M. A., Khodairy, A. A.-B. A. G., Ghattas, A.-B. A. G. & Younes, S. (2004). J. Chin. Chem. Soc. 51, 103-114.]); Khodairy (2007[Khodairy, M. A. (2007). J. Chin. Chem. Soc. 54, 93-102.]). For the diverse biological actvities of pyrazolidinedione-containing compounds, see: D'Alo et al. (1978[D'Alo, G., Conti, G., Gadel, S. & Dalla Vedova, R. (1978). Farm. Ed. Sci. 33, 106-116.]); Tawab et al. (1960[Tawab, S. A., Moustafa, A. & Kira, M. (1960). Nature, 186, 165-166.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13N3O3·0.5C2H6OS

  • Mr = 334.37

  • Triclinic, [P \overline 1]

  • a = 5.7740 (2) Å

  • b = 14.9402 (6) Å

  • c = 19.2441 (7) Å

  • α = 106.060 (1)°

  • β = 93.459 (1)°

  • γ = 92.653 (1)°

  • V = 1588.96 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 100 K

  • 0.47 × 0.14 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.990

  • 25749 measured reflections

  • 7370 independent reflections

  • 5874 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.112

  • S = 1.02

  • 7370 reflections

  • 453 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.51 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg6 are the centroids of the C11–C16 and C27–C32 phenyl rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O3 0.86 (2) 2.15 (2) 2.8265 (17) 135 (2)
O1—H1A⋯O5 0.85 (2) 1.80 (2) 2.6479 (17) 174 (2)
N3—H3A⋯O2i 0.88 (2) 1.90 (2) 2.7740 (17) 174 (2)
N4—H4A⋯O6 0.88 (2) 2.11 (2) 2.8050 (18) 136 (2)
O4—H4B⋯O7ii 0.85 (2) 1.76 (2) 2.6061 (18) 172 (2)
N6—H6⋯O6iii 0.88 (2) 1.92 (2) 2.7831 (19) 169 (2)
C34—H34B⋯O3iv 0.98 2.43 3.403 (3) 175
C29—H29⋯Cg3v 0.95 2.64 3.548 (2) 160
C33—H33CCg6vi 0.98 2.74 3.690 (2) 163
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+1; (iv) x-1, y+1, z; (v) x+1, y+1, z; (vi) x-1, y, z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); 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.]); 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

Pyrazolidinedione compounds have been used as a core precursor to prepare a diversity of heterocyclic systems owning to the acidic methylene function (Khodairy, 2007; Abdel-Rahman et al., 2004); Elnagdy & Ohta, 1973). Moreover, pyrazolidinones have exhibited a wide spectrum of biological activities such as antipyretic (Tawab et al., 1960) and antiinflammatory drugs (D'Alo et al., 1978). In this concept, we herein report the synthesis and crystal structure of the title compound.

As shown in Fig. 1, the asymmetric unit of the title compound (I) contains two crystallographically independent molecules (A with O1 and B with O4) of (4E)-4-{[(2-hydroxyphenyl)amino]methylidene}-1-phenylpyrazolidine-3,5-dione and one molecule of dimethyl sulfoxide solvate. In molecule A, the benzene and phenyl rings are oriented at dihedral angles of 15.87 (8) and 9.97 (8) ° with respect to the pyrazolidine ring. In molecule B, the corresponding angles are 6.55 (9) and 9.80 (9) °, respectively.

Intramolecular N—H···O hydrogen bonds form S(5)S(6) motifs (Bernstein et al., 1995). Pairs of molecules are linked by N—H···O forming a dimer with R22(8) motifs (Table 1, Fig. 2). These dimers are also connected with the other molecules through the DMSO solvate molecules via O—H···O hydrogen generating bonds ribbons along b a-xis. Furthermore C—H···π interactions are observed between the ribbons (Table 1).

Related literature top

For the significant role of pyrazolidinediones in the synthesis of various heterocyclic compounds, see: Elnagdy & Ohta (1973); Abdel-Rahman et al. (2004); Khodairy (2007). For the diverse biological actvities of pyrazolidinedione-containing compounds, see: D'Alo et al. (1978); Tawab et al. (1960). For graph-set motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of (4Z)-4-[(dimethylamino)methylidene]-1-phenylpyrazolidine-3,5-dione (231 mg, 1 mmol) and 2-aminophenol (109 mg, 1 mmol) in 50 ml acetic acid was refluxed for 2 h. The resulting solid on hot was filtered off, dried under vacuum, washed with ethanol and recrystallized from dimethyl sufoxide to afford the title compound in good quality crystals (M.p.: 541 - 542 K) sufficient for X-ray diffraction.

Refinement top

The C-bound H atoms were placed in geometrically idealized positions [C—H = 0.95 Å for aromatic H and C—H = 0.98 Å for methyl H] and were refined using a riding model with Uiso(H) = 1.2Ueq(Caromatic) and 1.5Ueq(Cmethyl). Hydroxyl and amine H atoms are found from difference Fourier maps and refined with constraints of N—H = 0.88 (2) and O—H = 0.84 (2) Å, Uiso(H) = 1.2Ueq(N) for amine H atoms and Uiso(H) = 1.5Ueq(O) for hydroxyl 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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the N—H···O dimers and O—H···O and N—H···O hydrogen bonding (dashed lines) down the b axis of the title compound.
(4E)-4-[(2-Hydroxyanilino)methylidene]-1-phenylpyrazolidine-3,5-dione dimethyl sulfoxide hemisolvate top
Crystal data top
C16H13N3O3·0.5C2H6OSZ = 4
Mr = 334.37F(000) = 700
Triclinic, P1Dx = 1.398 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7740 (2) ÅCell parameters from 9951 reflections
b = 14.9402 (6) Åθ = 2.8–27.6°
c = 19.2441 (7) ŵ = 0.16 mm1
α = 106.060 (1)°T = 100 K
β = 93.459 (1)°Prism, colourless
γ = 92.653 (1)°0.47 × 0.14 × 0.06 mm
V = 1588.96 (10) Å3
Data collection top
Bruker APEXII CCD
diffractometer
7370 independent reflections
Radiation source: sealed tube5874 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ϕ and ω scansθmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 76
Tmin = 0.973, Tmax = 0.990k = 1919
25749 measured reflectionsl = 2425
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044 W = 1/[Σ2(FO2) + (0.0457P)2 + 1.0131P] WHERE P = (FO2 + 2FC2)/3
wR(F2) = 0.112(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.40 e Å3
7370 reflectionsΔρmin = 0.51 e Å3
453 parameters
Crystal data top
C16H13N3O3·0.5C2H6OSγ = 92.653 (1)°
Mr = 334.37V = 1588.96 (10) Å3
Triclinic, P1Z = 4
a = 5.7740 (2) ÅMo Kα radiation
b = 14.9402 (6) ŵ = 0.16 mm1
c = 19.2441 (7) ÅT = 100 K
α = 106.060 (1)°0.47 × 0.14 × 0.06 mm
β = 93.459 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
7370 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
5874 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.990Rint = 0.043
25749 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0446 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.02Δρmax = 0.40 e Å3
7370 reflectionsΔρmin = 0.51 e Å3
453 parameters
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
O11.0470 (2)0.31031 (8)0.80151 (7)0.0235 (3)
O20.65665 (19)0.04836 (8)0.93836 (7)0.0239 (4)
O31.2614 (2)0.09699 (8)0.84559 (7)0.0249 (4)
N10.8575 (2)0.19791 (9)0.86858 (7)0.0176 (4)
N21.0350 (2)0.07965 (9)0.91086 (7)0.0165 (4)
N31.2123 (2)0.04078 (9)0.87775 (8)0.0187 (4)
C10.8647 (3)0.34333 (11)0.83966 (8)0.0182 (4)
C20.7821 (3)0.43089 (11)0.84613 (9)0.0236 (5)
C30.5912 (3)0.45743 (11)0.88502 (10)0.0258 (5)
C40.4791 (3)0.39733 (11)0.91716 (9)0.0236 (5)
C50.5609 (3)0.30982 (11)0.91163 (9)0.0203 (4)
C60.7542 (3)0.28328 (10)0.87382 (8)0.0166 (4)
C70.7803 (3)0.12843 (10)0.89313 (8)0.0174 (4)
C80.9069 (3)0.05182 (10)0.89051 (8)0.0162 (4)
C90.8422 (3)0.02722 (10)0.91639 (8)0.0162 (4)
C101.1384 (3)0.04256 (10)0.86849 (9)0.0178 (4)
C111.0542 (3)0.17105 (10)0.91722 (8)0.0154 (4)
C120.8869 (3)0.21227 (11)0.95024 (8)0.0184 (4)
C130.9161 (3)0.30103 (11)0.95758 (9)0.0217 (5)
C141.1073 (3)0.34943 (11)0.93344 (9)0.0228 (5)
C151.2715 (3)0.30817 (11)0.90057 (10)0.0238 (5)
C161.2464 (3)0.21971 (11)0.89186 (9)0.0200 (5)
O40.3509 (2)0.22169 (9)0.47285 (7)0.0331 (4)
O51.2172 (2)0.43434 (8)0.73963 (6)0.0242 (4)
O60.8410 (2)0.39366 (8)0.50665 (6)0.0230 (3)
N40.6176 (2)0.29482 (9)0.59083 (7)0.0197 (4)
N51.2770 (2)0.49105 (9)0.64119 (7)0.0179 (4)
N61.1791 (2)0.47253 (10)0.56906 (7)0.0195 (4)
C170.2873 (3)0.19598 (12)0.53154 (9)0.0244 (5)
C180.0972 (3)0.13555 (13)0.53120 (10)0.0299 (5)
C190.0470 (3)0.11388 (13)0.59430 (11)0.0321 (6)
C200.1841 (3)0.15263 (13)0.65813 (10)0.0305 (6)
C210.3754 (3)0.21364 (12)0.65940 (9)0.0248 (5)
C220.4276 (3)0.23438 (11)0.59601 (9)0.0206 (5)
C230.7898 (3)0.33169 (11)0.64012 (9)0.0188 (4)
C240.9671 (3)0.38897 (11)0.62757 (8)0.0181 (4)
C251.1586 (3)0.43738 (10)0.67724 (8)0.0182 (4)
C260.9804 (3)0.41578 (11)0.56190 (8)0.0186 (4)
C271.4860 (3)0.54793 (10)0.66204 (8)0.0176 (4)
C281.5761 (3)0.57334 (12)0.73415 (9)0.0228 (5)
C291.7817 (3)0.62903 (12)0.75405 (10)0.0270 (5)
C301.8980 (3)0.66043 (12)0.70351 (10)0.0250 (5)
C311.8058 (3)0.63606 (12)0.63225 (9)0.0232 (5)
C321.6008 (3)0.58009 (11)0.61100 (9)0.0206 (5)
S10.71959 (8)0.90279 (3)0.71557 (2)0.0305 (2)
O70.8621 (2)0.87145 (9)0.65113 (7)0.0334 (4)
C330.4512 (4)0.83276 (15)0.69636 (13)0.0416 (7)
C340.6075 (4)1.00954 (15)0.70907 (12)0.0418 (7)
H10.990 (3)0.1921 (13)0.8499 (10)0.0210*
H1A1.108 (4)0.3515 (13)0.7841 (11)0.0350*
H20.856800.472500.823800.0280*
H30.536400.517600.889700.0310*
H3A1.352 (3)0.0388 (13)0.8987 (10)0.0220*
H40.346200.415800.943000.0280*
H50.484300.268400.933700.0240*
H70.633400.131500.913100.0210*
H120.754700.179900.967500.0220*
H130.801700.329200.979800.0260*
H141.125700.409900.939300.0270*
H151.403700.340800.883700.0290*
H161.359800.192500.868700.0240*
H4A0.627 (3)0.3061 (13)0.5487 (9)0.0240*
H4B0.269 (4)0.1914 (16)0.4344 (10)0.0500*
H61.177 (3)0.5205 (11)0.5509 (10)0.0230*
H180.001600.109100.487700.0360*
H190.082600.072100.593800.0390*
H200.147600.137600.701200.0370*
H210.468900.240700.703200.0300*
H230.791800.318400.685700.0230*
H281.497400.552700.769400.0270*
H291.843700.645900.803100.0320*
H302.039200.698200.717600.0300*
H311.883700.657900.597400.0280*
H321.539100.563800.561900.0250*
H33A0.380800.833100.648800.0620*
H33B0.345000.858200.733700.0620*
H33C0.480700.768600.696000.0620*
H34A0.736101.056800.715000.0630*
H34B0.500901.030900.747100.0630*
H34C0.523700.999600.661400.0630*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0266 (6)0.0209 (6)0.0281 (6)0.0018 (5)0.0080 (5)0.0139 (5)
O20.0160 (6)0.0201 (6)0.0412 (7)0.0035 (4)0.0091 (5)0.0161 (5)
O30.0213 (6)0.0220 (6)0.0378 (7)0.0022 (5)0.0096 (5)0.0174 (5)
N10.0173 (7)0.0149 (6)0.0222 (7)0.0021 (5)0.0031 (5)0.0075 (5)
N20.0139 (6)0.0140 (6)0.0243 (7)0.0008 (5)0.0050 (5)0.0090 (5)
N30.0135 (6)0.0177 (6)0.0290 (7)0.0021 (5)0.0062 (6)0.0124 (6)
C10.0208 (8)0.0168 (7)0.0170 (8)0.0007 (6)0.0019 (6)0.0059 (6)
C20.0320 (9)0.0171 (8)0.0248 (9)0.0001 (7)0.0017 (7)0.0115 (6)
C30.0376 (10)0.0145 (8)0.0274 (9)0.0065 (7)0.0013 (7)0.0088 (6)
C40.0277 (9)0.0195 (8)0.0246 (9)0.0073 (7)0.0046 (7)0.0065 (6)
C50.0233 (8)0.0163 (7)0.0236 (8)0.0017 (6)0.0031 (7)0.0091 (6)
C60.0198 (8)0.0121 (7)0.0175 (8)0.0003 (6)0.0029 (6)0.0047 (6)
C70.0159 (7)0.0147 (7)0.0217 (8)0.0001 (6)0.0003 (6)0.0058 (6)
C80.0158 (7)0.0141 (7)0.0190 (8)0.0011 (6)0.0010 (6)0.0056 (6)
C90.0152 (7)0.0141 (7)0.0200 (8)0.0015 (6)0.0014 (6)0.0057 (6)
C100.0185 (8)0.0148 (7)0.0209 (8)0.0015 (6)0.0028 (6)0.0061 (6)
C110.0168 (7)0.0119 (7)0.0176 (7)0.0001 (6)0.0024 (6)0.0052 (5)
C120.0179 (8)0.0183 (7)0.0202 (8)0.0018 (6)0.0026 (6)0.0073 (6)
C130.0241 (8)0.0197 (8)0.0235 (8)0.0024 (6)0.0008 (7)0.0108 (6)
C140.0262 (9)0.0157 (7)0.0283 (9)0.0010 (6)0.0041 (7)0.0103 (6)
C150.0194 (8)0.0169 (8)0.0350 (10)0.0046 (6)0.0004 (7)0.0071 (7)
C160.0161 (8)0.0167 (7)0.0288 (9)0.0007 (6)0.0016 (6)0.0089 (6)
O40.0378 (8)0.0395 (8)0.0194 (6)0.0165 (6)0.0023 (6)0.0081 (5)
O50.0292 (7)0.0270 (6)0.0188 (6)0.0069 (5)0.0028 (5)0.0126 (5)
O60.0244 (6)0.0276 (6)0.0176 (6)0.0066 (5)0.0017 (5)0.0095 (5)
N40.0226 (7)0.0205 (7)0.0174 (7)0.0027 (5)0.0025 (6)0.0079 (5)
N50.0202 (7)0.0210 (7)0.0137 (6)0.0012 (5)0.0004 (5)0.0077 (5)
N60.0222 (7)0.0236 (7)0.0137 (6)0.0039 (6)0.0011 (5)0.0085 (5)
C170.0282 (9)0.0221 (8)0.0219 (8)0.0017 (7)0.0047 (7)0.0043 (6)
C180.0293 (10)0.0280 (9)0.0275 (9)0.0079 (7)0.0025 (7)0.0012 (7)
C190.0299 (10)0.0266 (9)0.0373 (11)0.0098 (7)0.0108 (8)0.0048 (8)
C200.0343 (10)0.0294 (9)0.0302 (10)0.0033 (8)0.0123 (8)0.0114 (7)
C210.0262 (9)0.0252 (9)0.0237 (9)0.0004 (7)0.0039 (7)0.0079 (7)
C220.0204 (8)0.0171 (8)0.0249 (8)0.0006 (6)0.0050 (7)0.0063 (6)
C230.0233 (8)0.0171 (7)0.0178 (8)0.0023 (6)0.0036 (6)0.0073 (6)
C240.0213 (8)0.0171 (7)0.0164 (8)0.0013 (6)0.0022 (6)0.0056 (6)
C250.0214 (8)0.0161 (7)0.0185 (8)0.0006 (6)0.0035 (6)0.0070 (6)
C260.0197 (8)0.0182 (7)0.0185 (8)0.0004 (6)0.0027 (6)0.0061 (6)
C270.0180 (8)0.0162 (7)0.0191 (8)0.0018 (6)0.0024 (6)0.0057 (6)
C280.0271 (9)0.0242 (8)0.0187 (8)0.0026 (7)0.0022 (7)0.0092 (6)
C290.0297 (10)0.0286 (9)0.0223 (9)0.0059 (7)0.0057 (7)0.0095 (7)
C300.0206 (8)0.0245 (8)0.0299 (9)0.0047 (7)0.0009 (7)0.0092 (7)
C310.0232 (8)0.0244 (8)0.0240 (9)0.0003 (7)0.0069 (7)0.0093 (7)
C320.0224 (8)0.0224 (8)0.0173 (8)0.0000 (6)0.0029 (6)0.0061 (6)
S10.0324 (3)0.0342 (3)0.0215 (2)0.0017 (2)0.0025 (2)0.0020 (2)
O70.0256 (7)0.0396 (8)0.0272 (7)0.0041 (6)0.0038 (5)0.0030 (6)
C330.0305 (11)0.0439 (12)0.0501 (13)0.0012 (9)0.0145 (10)0.0106 (10)
C340.0533 (14)0.0372 (11)0.0369 (11)0.0086 (10)0.0160 (10)0.0102 (9)
Geometric parameters (Å, º) top
S1—C341.782 (2)C2—H20.9500
S1—O71.5072 (13)C3—H30.9500
S1—C331.789 (2)C4—H40.9500
O1—C11.353 (2)C5—H50.9500
O2—C91.234 (2)C7—H70.9500
O3—C101.242 (2)C12—H120.9500
O1—H1A0.85 (2)C13—H130.9500
O4—C171.355 (2)C14—H140.9500
O5—C251.2412 (19)C15—H150.9500
O6—C261.2511 (19)C16—H160.9500
O4—H4B0.85 (2)C17—C221.402 (2)
N1—C71.324 (2)C17—C181.387 (3)
N1—C61.414 (2)C18—C191.384 (3)
N2—C111.413 (2)C19—C201.385 (3)
N2—N31.4212 (18)C20—C211.394 (3)
N2—C91.383 (2)C21—C221.386 (2)
N3—C101.388 (2)C23—C241.379 (2)
N1—H10.863 (18)C24—C251.441 (2)
N3—H3A0.875 (18)C24—C261.433 (2)
N4—C231.318 (2)C27—C321.395 (2)
N4—C221.414 (2)C27—C281.394 (2)
N5—C271.413 (2)C28—C291.388 (3)
N5—N61.4146 (18)C29—C301.385 (3)
N5—C251.381 (2)C30—C311.384 (2)
N6—C261.371 (2)C31—C321.389 (2)
N4—H4A0.877 (17)C18—H180.9500
N6—H60.880 (17)C19—H190.9500
C1—C61.403 (2)C20—H200.9500
C1—C21.389 (2)C21—H210.9500
C2—C31.381 (2)C23—H230.9500
C3—C41.382 (2)C28—H280.9500
C4—C51.389 (2)C29—H290.9500
C5—C61.383 (2)C30—H300.9500
C7—C81.377 (2)C31—H310.9500
C8—C101.428 (2)C32—H320.9500
C8—C91.445 (2)C33—H33A0.9800
C11—C161.394 (2)C33—H33B0.9800
C11—C121.397 (2)C33—H33C0.9800
C12—C131.389 (2)C34—H34A0.9800
C13—C141.381 (2)C34—H34B0.9800
C14—C151.383 (2)C34—H34C0.9800
C15—C161.390 (2)
O7—S1—C33107.82 (9)C15—C14—H14121.00
O7—S1—C34105.34 (9)C14—C15—H15119.00
C33—S1—C3497.86 (11)C16—C15—H15119.00
C1—O1—H1A110.7 (15)C15—C16—H16120.00
C17—O4—H4B111.6 (15)C11—C16—H16120.00
C6—N1—C7127.16 (13)O4—C17—C18124.48 (16)
N3—N2—C9110.49 (13)O4—C17—C22115.99 (15)
N3—N2—C11118.54 (12)C18—C17—C22119.53 (16)
C9—N2—C11129.12 (13)C17—C18—C19119.91 (17)
N2—N3—C10107.55 (12)C18—C19—C20120.53 (17)
C7—N1—H1116.5 (13)C19—C20—C21120.25 (17)
C6—N1—H1116.2 (13)C20—C21—C22119.24 (16)
C10—N3—H3A116.6 (13)C17—C22—C21120.52 (16)
N2—N3—H3A114.2 (12)N4—C22—C21124.13 (15)
C22—N4—C23127.91 (14)N4—C22—C17115.34 (15)
C25—N5—C27130.40 (13)N4—C23—C24121.98 (15)
N6—N5—C25110.15 (12)C23—C24—C26124.17 (15)
N6—N5—C27118.85 (12)C23—C24—C25127.93 (14)
N5—N6—C26108.04 (12)C25—C24—C26107.76 (14)
C22—N4—H4A116.0 (12)N5—C25—C24105.83 (13)
C23—N4—H4A116.0 (12)O5—C25—N5124.06 (15)
N5—N6—H6116.1 (12)O5—C25—C24130.11 (15)
C26—N6—H6119.1 (11)N6—C26—C24107.70 (14)
O1—C1—C2124.32 (15)O6—C26—C24128.32 (16)
O1—C1—C6116.43 (15)O6—C26—N6123.98 (14)
C2—C1—C6119.25 (15)N5—C27—C28119.95 (14)
C1—C2—C3119.97 (16)C28—C27—C32119.75 (16)
C2—C3—C4120.71 (16)N5—C27—C32120.29 (14)
C3—C4—C5119.95 (16)C27—C28—C29119.51 (16)
C4—C5—C6119.72 (16)C28—C29—C30121.06 (17)
C1—C6—C5120.38 (15)C29—C30—C31119.12 (16)
N1—C6—C1115.82 (14)C30—C31—C32120.86 (16)
N1—C6—C5123.78 (14)C27—C32—C31119.69 (15)
N1—C7—C8121.87 (15)C19—C18—H18120.00
C7—C8—C10124.68 (15)C17—C18—H18120.00
C9—C8—C10108.23 (14)C18—C19—H19120.00
C7—C8—C9126.77 (16)C20—C19—H19120.00
N2—C9—C8105.69 (14)C19—C20—H20120.00
O2—C9—N2124.45 (14)C21—C20—H20120.00
O2—C9—C8129.85 (16)C22—C21—H21120.00
N3—C10—C8107.75 (13)C20—C21—H21120.00
O3—C10—C8128.75 (15)C24—C23—H23119.00
O3—C10—N3123.49 (15)N4—C23—H23119.00
N2—C11—C16119.35 (14)C27—C28—H28120.00
N2—C11—C12121.03 (15)C29—C28—H28120.00
C12—C11—C16119.60 (15)C28—C29—H29119.00
C11—C12—C13119.25 (16)C30—C29—H29119.00
C12—C13—C14121.64 (16)C31—C30—H30120.00
C13—C14—C15118.67 (16)C29—C30—H30120.00
C14—C15—C16121.10 (16)C30—C31—H31120.00
C11—C16—C15119.73 (16)C32—C31—H31120.00
C1—C2—H2120.00C27—C32—H32120.00
C3—C2—H2120.00C31—C32—H32120.00
C2—C3—H3120.00S1—C33—H33A109.00
C4—C3—H3120.00S1—C33—H33B109.00
C5—C4—H4120.00S1—C33—H33C109.00
C3—C4—H4120.00H33A—C33—H33B109.00
C6—C5—H5120.00H33A—C33—H33C109.00
C4—C5—H5120.00H33B—C33—H33C109.00
C8—C7—H7119.00S1—C34—H34A109.00
N1—C7—H7119.00S1—C34—H34B110.00
C13—C12—H12120.00S1—C34—H34C109.00
C11—C12—H12120.00H34A—C34—H34B110.00
C14—C13—H13119.00H34A—C34—H34C109.00
C12—C13—H13119.00H34B—C34—H34C109.00
C13—C14—H14121.00
C6—N1—C7—C8174.14 (15)C7—C8—C9—N2172.41 (15)
C7—N1—C6—C55.4 (2)C10—C8—C9—O2177.61 (16)
C7—N1—C6—C1176.59 (15)C7—C8—C10—O33.3 (3)
C9—N2—C11—C1218.0 (2)C7—C8—C10—N3175.97 (15)
C11—N2—N3—C10171.57 (13)C7—C8—C9—O28.7 (3)
C11—N2—C9—O210.8 (3)C9—C8—C10—O3177.15 (17)
N3—N2—C11—C160.8 (2)C9—C8—C10—N32.08 (18)
C9—N2—C11—C16163.72 (15)N2—C11—C16—C15177.38 (15)
C9—N2—N3—C105.64 (17)C12—C11—C16—C150.9 (2)
C11—N2—C9—C8168.25 (14)N2—C11—C12—C13177.88 (14)
N3—N2—C11—C12179.05 (14)C16—C11—C12—C130.4 (2)
N3—N2—C9—O2174.78 (15)C11—C12—C13—C140.4 (2)
N3—N2—C9—C84.22 (16)C12—C13—C14—C150.7 (3)
N2—N3—C10—C84.60 (17)C13—C14—C15—C160.1 (3)
N2—N3—C10—O3174.69 (15)C14—C15—C16—C110.7 (3)
C23—N4—C22—C17171.75 (16)O4—C17—C22—C21179.01 (16)
C22—N4—C23—C24179.09 (16)C18—C17—C22—N4179.75 (16)
C23—N4—C22—C219.1 (3)O4—C17—C22—N40.2 (2)
N6—N5—C27—C28174.88 (15)O4—C17—C18—C19179.90 (17)
N6—N5—C27—C324.1 (2)C22—C17—C18—C190.2 (3)
C27—N5—C25—C24175.58 (15)C18—C17—C22—C211.1 (3)
N6—N5—C25—O5174.60 (15)C17—C18—C19—C200.5 (3)
C25—N5—C27—C2815.0 (3)C18—C19—C20—C210.4 (3)
C27—N5—C25—O53.8 (3)C19—C20—C21—C220.5 (3)
C25—N5—C27—C32166.08 (16)C20—C21—C22—C171.2 (3)
C27—N5—N6—C26179.47 (14)C20—C21—C22—N4179.68 (16)
C25—N5—N6—C267.45 (17)N4—C23—C24—C261.5 (3)
N6—N5—C25—C244.77 (17)N4—C23—C24—C25176.69 (16)
N5—N6—C26—O6172.99 (15)C26—C24—C25—N50.50 (18)
N5—N6—C26—C246.87 (18)C23—C24—C26—O60.2 (3)
C2—C1—C6—N1176.10 (14)C23—C24—C26—N6179.97 (16)
O1—C1—C6—N14.4 (2)C25—C24—C26—O6175.85 (17)
O1—C1—C6—C5177.50 (15)C25—C24—C26—N64.01 (19)
C6—C1—C2—C30.9 (2)C23—C24—C25—O55.4 (3)
O1—C1—C2—C3178.54 (16)C23—C24—C25—N5175.32 (17)
C2—C1—C6—C52.0 (2)C26—C24—C25—O5178.81 (17)
C1—C2—C3—C40.7 (3)N5—C27—C28—C29179.85 (15)
C2—C3—C4—C51.2 (3)C32—C27—C28—C291.2 (3)
C3—C4—C5—C60.1 (3)N5—C27—C32—C31179.89 (16)
C4—C5—C6—N1176.44 (15)C28—C27—C32—C310.9 (3)
C4—C5—C6—C11.5 (2)C27—C28—C29—C300.5 (3)
N1—C7—C8—C106.4 (2)C28—C29—C30—C310.4 (3)
N1—C7—C8—C9179.11 (15)C29—C30—C31—C320.7 (3)
C10—C8—C9—N21.32 (17)C30—C31—C32—C270.0 (3)
Hydrogen-bond geometry (Å, º) top
Cg3 and Cg6 are the centroids of the C11–C16 and C27–C32 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.86 (2)2.23 (2)2.6235 (18)107 (2)
N1—H1···O30.86 (2)2.15 (2)2.8265 (17)135 (2)
O1—H1A···O50.85 (2)1.80 (2)2.6479 (17)174 (2)
N3—H3A···O2i0.88 (2)1.90 (2)2.7740 (17)174 (2)
N4—H4A···O40.88 (2)2.19 (2)2.6019 (18)109 (2)
N4—H4A···O60.88 (2)2.11 (2)2.8050 (18)136 (2)
O4—H4B···S1ii0.85 (2)2.85 (2)3.5767 (14)145 (2)
O4—H4B···O7ii0.85 (2)1.76 (2)2.6061 (18)172 (2)
N6—H6···O6iii0.88 (2)1.92 (2)2.7831 (19)169 (2)
C7—H7···O3iv0.952.403.055 (2)126
C12—H12···O20.952.272.897 (2)122
C16—H16···N30.952.422.775 (2)102
C28—H28···O50.952.272.893 (2)123
C32—H32···N60.952.462.801 (2)101
C34—H34B···O3v0.982.433.403 (3)175
C29—H29···Cg3vi0.952.643.548 (2)160
C33—H33C···Cg6iv0.982.743.690 (2)163
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1; (iv) x1, y, z; (v) x1, y+1, z; (vi) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg3 and Cg6 are the centroids of the C11–C16 and C27–C32 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.863 (18)2.154 (19)2.8265 (17)134.5 (17)
O1—H1A···O50.85 (2)1.80 (2)2.6479 (17)174 (2)
N3—H3A···O2i0.875 (18)1.902 (18)2.7740 (17)174 (2)
N4—H4A···O60.877 (17)2.109 (19)2.8050 (18)135.8 (15)
O4—H4B···S1ii0.85 (2)2.846 (19)3.5767 (14)144.7 (19)
O4—H4B···O7ii0.85 (2)1.76 (2)2.6061 (18)172 (2)
N6—H6···O6iii0.880 (17)1.915 (18)2.7831 (19)168.6 (17)
C34—H34B···O3iv0.982.433.403 (3)175
C29—H29···Cg3v0.952.643.548 (2)160
C33—H33C···Cg6vi0.982.743.690 (2)163
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1; (iv) x1, y+1, z; (v) x+1, y+1, z; (vi) x1, y, z.
 

Acknowledgements

Manchester Metropolitan University, Erciyes University and Granada University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzoń, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

References

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Volume 69| Part 9| September 2013| Pages o1408-o1409
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