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

Akkurt, M.; Mohamed, S.K.; Elremaily, M.A.A.; Ahmed, E.A.; Albayati, M.R.

doi:10.1107/S1600536813022034

organic compounds

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ISSN: 2056-9890

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

doi:10.1107/S1600536813022034

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

Mehmet Akkurt,^a Shaaban K. Mohamed,^b,^c Mahmoud A. A. Elremaily,^d,^e Eman. A. Ahmed ^f and Mustafa R. Albayati ^g ^*

^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 ); 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

Crystal data

C₁₆H₁₃N₃O₃·0.5C₂H₆OS
M_r = 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 ) T_min = 0.973, T_max = 0.990
25749 measured reflections
7370 independent reflections
5874 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.40 e Å⁻³
Δρ_min = −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	D⋯A	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⋯O3^iv	0.98	2.43	3.403 (3)	175
C29—H29⋯Cg3^v	0.95	2.64	3.548 (2)	160
C33—H33C⋯Cg6^vi	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 ); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813022034/hg5338sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813022034/hg5338Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813022034/hg5338Isup3.cml

checkCIF report

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.

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

	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.
	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

C₁₆H₁₃N₃O₃·0.5C₂H₆OS	Z = 4
M_r = 334.37	F(000) = 700
Triclinic, P1	D_x = 1.398 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7740 (2) Å	Cell parameters from 9951 reflections
b = 14.9402 (6) Å	θ = 2.8–27.6°
c = 19.2441 (7) Å	µ = 0.16 mm⁻¹
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 tube	5874 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −7→6
T_min = 0.973, T_max = 0.990	k = −19→19
25749 measured reflections	l = −24→25

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	H-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 = 1.02	Δρ_max = 0.40 e Å⁻³
7370 reflections	Δρ_min = −0.51 e Å⁻³
453 parameters

Crystal data top

C₁₆H₁₃N₃O₃·0.5C₂H₆OS	γ = 92.653 (1)°
M_r = 334.37	V = 1588.96 (10) Å³
Triclinic, P1	Z = 4
a = 5.7740 (2) Å	Mo Kα radiation
b = 14.9402 (6) Å	µ = 0.16 mm⁻¹
c = 19.2441 (7) Å	T = 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)
T_min = 0.973, T_max = 0.990	R_int = 0.043
25749 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	6 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.02	Δρ_max = 0.40 e Å⁻³
7370 reflections	Δρ_min = −0.51 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	1.0470 (2)	0.31031 (8)	0.80151 (7)	0.0235 (3)
O2	0.65665 (19)	−0.04836 (8)	0.93836 (7)	0.0239 (4)
O3	1.2614 (2)	0.09699 (8)	0.84559 (7)	0.0249 (4)
N1	0.8575 (2)	0.19791 (9)	0.86858 (7)	0.0176 (4)
N2	1.0350 (2)	−0.07965 (9)	0.91086 (7)	0.0165 (4)
N3	1.2123 (2)	−0.04078 (9)	0.87775 (8)	0.0187 (4)
C1	0.8647 (3)	0.34333 (11)	0.83966 (8)	0.0182 (4)
C2	0.7821 (3)	0.43089 (11)	0.84613 (9)	0.0236 (5)
C3	0.5912 (3)	0.45743 (11)	0.88502 (10)	0.0258 (5)
C4	0.4791 (3)	0.39733 (11)	0.91716 (9)	0.0236 (5)
C5	0.5609 (3)	0.30982 (11)	0.91163 (9)	0.0203 (4)
C6	0.7542 (3)	0.28328 (10)	0.87382 (8)	0.0166 (4)
C7	0.7803 (3)	0.12843 (10)	0.89313 (8)	0.0174 (4)
C8	0.9069 (3)	0.05182 (10)	0.89051 (8)	0.0162 (4)
C9	0.8422 (3)	−0.02722 (10)	0.91639 (8)	0.0162 (4)
C10	1.1384 (3)	0.04256 (10)	0.86849 (9)	0.0178 (4)
C11	1.0542 (3)	−0.17105 (10)	0.91722 (8)	0.0154 (4)
C12	0.8869 (3)	−0.21227 (11)	0.95024 (8)	0.0184 (4)
C13	0.9161 (3)	−0.30103 (11)	0.95758 (9)	0.0217 (5)
C14	1.1073 (3)	−0.34943 (11)	0.93344 (9)	0.0228 (5)
C15	1.2715 (3)	−0.30817 (11)	0.90057 (10)	0.0238 (5)
C16	1.2464 (3)	−0.21971 (11)	0.89186 (9)	0.0200 (5)
O4	0.3509 (2)	0.22169 (9)	0.47285 (7)	0.0331 (4)
O5	1.2172 (2)	0.43434 (8)	0.73963 (6)	0.0242 (4)
O6	0.8410 (2)	0.39366 (8)	0.50665 (6)	0.0230 (3)
N4	0.6176 (2)	0.29482 (9)	0.59083 (7)	0.0197 (4)
N5	1.2770 (2)	0.49105 (9)	0.64119 (7)	0.0179 (4)
N6	1.1791 (2)	0.47253 (10)	0.56906 (7)	0.0195 (4)
C17	0.2873 (3)	0.19598 (12)	0.53154 (9)	0.0244 (5)
C18	0.0972 (3)	0.13555 (13)	0.53120 (10)	0.0299 (5)
C19	0.0470 (3)	0.11388 (13)	0.59430 (11)	0.0321 (6)
C20	0.1841 (3)	0.15263 (13)	0.65813 (10)	0.0305 (6)
C21	0.3754 (3)	0.21364 (12)	0.65940 (9)	0.0248 (5)
C22	0.4276 (3)	0.23438 (11)	0.59601 (9)	0.0206 (5)
C23	0.7898 (3)	0.33169 (11)	0.64012 (9)	0.0188 (4)
C24	0.9671 (3)	0.38897 (11)	0.62757 (8)	0.0181 (4)
C25	1.1586 (3)	0.43738 (10)	0.67724 (8)	0.0182 (4)
C26	0.9804 (3)	0.41578 (11)	0.56190 (8)	0.0186 (4)
C27	1.4860 (3)	0.54793 (10)	0.66204 (8)	0.0176 (4)
C28	1.5761 (3)	0.57334 (12)	0.73415 (9)	0.0228 (5)
C29	1.7817 (3)	0.62903 (12)	0.75405 (10)	0.0270 (5)
C30	1.8980 (3)	0.66043 (12)	0.70351 (10)	0.0250 (5)
C31	1.8058 (3)	0.63606 (12)	0.63225 (9)	0.0232 (5)
C32	1.6008 (3)	0.58009 (11)	0.61100 (9)	0.0206 (5)
S1	0.71959 (8)	0.90279 (3)	0.71557 (2)	0.0305 (2)
O7	0.8621 (2)	0.87145 (9)	0.65113 (7)	0.0334 (4)
C33	0.4512 (4)	0.83276 (15)	0.69636 (13)	0.0416 (7)
C34	0.6075 (4)	1.00954 (15)	0.70907 (12)	0.0418 (7)
H1	0.990 (3)	0.1921 (13)	0.8499 (10)	0.0210*
H1A	1.108 (4)	0.3515 (13)	0.7841 (11)	0.0350*
H2	0.85680	0.47250	0.82380	0.0280*
H3	0.53640	0.51760	0.88970	0.0310*
H3A	1.352 (3)	−0.0388 (13)	0.8987 (10)	0.0220*
H4	0.34620	0.41580	0.94300	0.0280*
H5	0.48430	0.26840	0.93370	0.0240*
H7	0.63340	0.13150	0.91310	0.0210*
H12	0.75470	−0.17990	0.96750	0.0220*
H13	0.80170	−0.32920	0.97980	0.0260*
H14	1.12570	−0.40990	0.93930	0.0270*
H15	1.40370	−0.34080	0.88370	0.0290*
H16	1.35980	−0.19250	0.86870	0.0240*
H4A	0.627 (3)	0.3061 (13)	0.5487 (9)	0.0240*
H4B	0.269 (4)	0.1914 (16)	0.4344 (10)	0.0500*
H6	1.177 (3)	0.5205 (11)	0.5509 (10)	0.0230*
H18	0.00160	0.10910	0.48770	0.0360*
H19	−0.08260	0.07210	0.59380	0.0390*
H20	0.14760	0.13760	0.70120	0.0370*
H21	0.46890	0.24070	0.70320	0.0300*
H23	0.79180	0.31840	0.68570	0.0230*
H28	1.49740	0.55270	0.76940	0.0270*
H29	1.84370	0.64590	0.80310	0.0320*
H30	2.03920	0.69820	0.71760	0.0300*
H31	1.88370	0.65790	0.59740	0.0280*
H32	1.53910	0.56380	0.56190	0.0250*
H33A	0.38080	0.83310	0.64880	0.0620*
H33B	0.34500	0.85820	0.73370	0.0620*
H33C	0.48070	0.76860	0.69600	0.0620*
H34A	0.73610	1.05680	0.71500	0.0630*
H34B	0.50090	1.03090	0.74710	0.0630*
H34C	0.52370	0.99960	0.66140	0.0630*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0266 (6)	0.0209 (6)	0.0281 (6)	0.0018 (5)	0.0080 (5)	0.0139 (5)
O2	0.0160 (6)	0.0201 (6)	0.0412 (7)	0.0035 (4)	0.0091 (5)	0.0161 (5)
O3	0.0213 (6)	0.0220 (6)	0.0378 (7)	0.0022 (5)	0.0096 (5)	0.0174 (5)
N1	0.0173 (7)	0.0149 (6)	0.0222 (7)	0.0021 (5)	0.0031 (5)	0.0075 (5)
N2	0.0139 (6)	0.0140 (6)	0.0243 (7)	0.0008 (5)	0.0050 (5)	0.0090 (5)
N3	0.0135 (6)	0.0177 (6)	0.0290 (7)	0.0021 (5)	0.0062 (6)	0.0124 (6)
C1	0.0208 (8)	0.0168 (7)	0.0170 (8)	−0.0007 (6)	−0.0019 (6)	0.0059 (6)
C2	0.0320 (9)	0.0171 (8)	0.0248 (9)	0.0001 (7)	0.0017 (7)	0.0115 (6)
C3	0.0376 (10)	0.0145 (8)	0.0274 (9)	0.0065 (7)	0.0013 (7)	0.0088 (6)
C4	0.0277 (9)	0.0195 (8)	0.0246 (9)	0.0073 (7)	0.0046 (7)	0.0065 (6)
C5	0.0233 (8)	0.0163 (7)	0.0236 (8)	0.0017 (6)	0.0031 (7)	0.0091 (6)
C6	0.0198 (8)	0.0121 (7)	0.0175 (8)	0.0003 (6)	−0.0029 (6)	0.0047 (6)
C7	0.0159 (7)	0.0147 (7)	0.0217 (8)	0.0001 (6)	0.0003 (6)	0.0058 (6)
C8	0.0158 (7)	0.0141 (7)	0.0190 (8)	−0.0011 (6)	0.0010 (6)	0.0056 (6)
C9	0.0152 (7)	0.0141 (7)	0.0200 (8)	0.0015 (6)	0.0014 (6)	0.0057 (6)
C10	0.0185 (8)	0.0148 (7)	0.0209 (8)	0.0015 (6)	0.0028 (6)	0.0061 (6)
C11	0.0168 (7)	0.0119 (7)	0.0176 (7)	−0.0001 (6)	−0.0024 (6)	0.0052 (5)
C12	0.0179 (8)	0.0183 (7)	0.0202 (8)	0.0018 (6)	0.0026 (6)	0.0073 (6)
C13	0.0241 (8)	0.0197 (8)	0.0235 (8)	−0.0024 (6)	0.0008 (7)	0.0108 (6)
C14	0.0262 (9)	0.0157 (7)	0.0283 (9)	0.0010 (6)	−0.0041 (7)	0.0103 (6)
C15	0.0194 (8)	0.0169 (8)	0.0350 (10)	0.0046 (6)	0.0004 (7)	0.0071 (7)
C16	0.0161 (8)	0.0167 (7)	0.0288 (9)	0.0007 (6)	0.0016 (6)	0.0089 (6)
O4	0.0378 (8)	0.0395 (8)	0.0194 (6)	−0.0165 (6)	−0.0023 (6)	0.0081 (5)
O5	0.0292 (7)	0.0270 (6)	0.0188 (6)	−0.0069 (5)	−0.0028 (5)	0.0126 (5)
O6	0.0244 (6)	0.0276 (6)	0.0176 (6)	−0.0066 (5)	−0.0017 (5)	0.0095 (5)
N4	0.0226 (7)	0.0205 (7)	0.0174 (7)	−0.0027 (5)	0.0025 (6)	0.0079 (5)
N5	0.0202 (7)	0.0210 (7)	0.0137 (6)	−0.0012 (5)	0.0004 (5)	0.0077 (5)
N6	0.0222 (7)	0.0236 (7)	0.0137 (6)	−0.0039 (6)	−0.0011 (5)	0.0085 (5)
C17	0.0282 (9)	0.0221 (8)	0.0219 (8)	−0.0017 (7)	0.0047 (7)	0.0043 (6)
C18	0.0293 (10)	0.0280 (9)	0.0275 (9)	−0.0079 (7)	0.0025 (7)	0.0012 (7)
C19	0.0299 (10)	0.0266 (9)	0.0373 (11)	−0.0098 (7)	0.0108 (8)	0.0048 (8)
C20	0.0343 (10)	0.0294 (9)	0.0302 (10)	−0.0033 (8)	0.0123 (8)	0.0114 (7)
C21	0.0262 (9)	0.0252 (9)	0.0237 (9)	−0.0004 (7)	0.0039 (7)	0.0079 (7)
C22	0.0204 (8)	0.0171 (8)	0.0249 (8)	−0.0006 (6)	0.0050 (7)	0.0063 (6)
C23	0.0233 (8)	0.0171 (7)	0.0178 (8)	0.0023 (6)	0.0036 (6)	0.0073 (6)
C24	0.0213 (8)	0.0171 (7)	0.0164 (8)	0.0013 (6)	0.0022 (6)	0.0056 (6)
C25	0.0214 (8)	0.0161 (7)	0.0185 (8)	0.0006 (6)	0.0035 (6)	0.0070 (6)
C26	0.0197 (8)	0.0182 (7)	0.0185 (8)	0.0004 (6)	0.0027 (6)	0.0061 (6)
C27	0.0180 (8)	0.0162 (7)	0.0191 (8)	0.0018 (6)	0.0024 (6)	0.0057 (6)
C28	0.0271 (9)	0.0242 (8)	0.0187 (8)	−0.0026 (7)	0.0022 (7)	0.0092 (6)
C29	0.0297 (10)	0.0286 (9)	0.0223 (9)	−0.0059 (7)	−0.0057 (7)	0.0095 (7)
C30	0.0206 (8)	0.0245 (8)	0.0299 (9)	−0.0047 (7)	−0.0009 (7)	0.0092 (7)
C31	0.0232 (8)	0.0244 (8)	0.0240 (9)	−0.0003 (7)	0.0069 (7)	0.0093 (7)
C32	0.0224 (8)	0.0224 (8)	0.0173 (8)	0.0000 (6)	0.0029 (6)	0.0061 (6)
S1	0.0324 (3)	0.0342 (3)	0.0215 (2)	0.0017 (2)	0.0025 (2)	0.0020 (2)
O7	0.0256 (7)	0.0396 (8)	0.0272 (7)	−0.0041 (6)	0.0038 (5)	−0.0030 (6)
C33	0.0305 (11)	0.0439 (12)	0.0501 (13)	0.0012 (9)	0.0145 (10)	0.0106 (10)
C34	0.0533 (14)	0.0372 (11)	0.0369 (11)	0.0086 (10)	0.0160 (10)	0.0102 (9)

Geometric parameters (Å, º) top

S1—C34	1.782 (2)	C2—H2	0.9500
S1—O7	1.5072 (13)	C3—H3	0.9500
S1—C33	1.789 (2)	C4—H4	0.9500
O1—C1	1.353 (2)	C5—H5	0.9500
O2—C9	1.234 (2)	C7—H7	0.9500
O3—C10	1.242 (2)	C12—H12	0.9500
O1—H1A	0.85 (2)	C13—H13	0.9500
O4—C17	1.355 (2)	C14—H14	0.9500
O5—C25	1.2412 (19)	C15—H15	0.9500
O6—C26	1.2511 (19)	C16—H16	0.9500
O4—H4B	0.85 (2)	C17—C22	1.402 (2)
N1—C7	1.324 (2)	C17—C18	1.387 (3)
N1—C6	1.414 (2)	C18—C19	1.384 (3)
N2—C11	1.413 (2)	C19—C20	1.385 (3)
N2—N3	1.4212 (18)	C20—C21	1.394 (3)
N2—C9	1.383 (2)	C21—C22	1.386 (2)
N3—C10	1.388 (2)	C23—C24	1.379 (2)
N1—H1	0.863 (18)	C24—C25	1.441 (2)
N3—H3A	0.875 (18)	C24—C26	1.433 (2)
N4—C23	1.318 (2)	C27—C32	1.395 (2)
N4—C22	1.414 (2)	C27—C28	1.394 (2)
N5—C27	1.413 (2)	C28—C29	1.388 (3)
N5—N6	1.4146 (18)	C29—C30	1.385 (3)
N5—C25	1.381 (2)	C30—C31	1.384 (2)
N6—C26	1.371 (2)	C31—C32	1.389 (2)
N4—H4A	0.877 (17)	C18—H18	0.9500
N6—H6	0.880 (17)	C19—H19	0.9500
C1—C6	1.403 (2)	C20—H20	0.9500
C1—C2	1.389 (2)	C21—H21	0.9500
C2—C3	1.381 (2)	C23—H23	0.9500
C3—C4	1.382 (2)	C28—H28	0.9500
C4—C5	1.389 (2)	C29—H29	0.9500
C5—C6	1.383 (2)	C30—H30	0.9500
C7—C8	1.377 (2)	C31—H31	0.9500
C8—C10	1.428 (2)	C32—H32	0.9500
C8—C9	1.445 (2)	C33—H33A	0.9800
C11—C16	1.394 (2)	C33—H33B	0.9800
C11—C12	1.397 (2)	C33—H33C	0.9800
C12—C13	1.389 (2)	C34—H34A	0.9800
C13—C14	1.381 (2)	C34—H34B	0.9800
C14—C15	1.383 (2)	C34—H34C	0.9800
C15—C16	1.390 (2)

O7—S1—C33	107.82 (9)	C15—C14—H14	121.00
O7—S1—C34	105.34 (9)	C14—C15—H15	119.00
C33—S1—C34	97.86 (11)	C16—C15—H15	119.00
C1—O1—H1A	110.7 (15)	C15—C16—H16	120.00
C17—O4—H4B	111.6 (15)	C11—C16—H16	120.00
C6—N1—C7	127.16 (13)	O4—C17—C18	124.48 (16)
N3—N2—C9	110.49 (13)	O4—C17—C22	115.99 (15)
N3—N2—C11	118.54 (12)	C18—C17—C22	119.53 (16)
C9—N2—C11	129.12 (13)	C17—C18—C19	119.91 (17)
N2—N3—C10	107.55 (12)	C18—C19—C20	120.53 (17)
C7—N1—H1	116.5 (13)	C19—C20—C21	120.25 (17)
C6—N1—H1	116.2 (13)	C20—C21—C22	119.24 (16)
C10—N3—H3A	116.6 (13)	C17—C22—C21	120.52 (16)
N2—N3—H3A	114.2 (12)	N4—C22—C21	124.13 (15)
C22—N4—C23	127.91 (14)	N4—C22—C17	115.34 (15)
C25—N5—C27	130.40 (13)	N4—C23—C24	121.98 (15)
N6—N5—C25	110.15 (12)	C23—C24—C26	124.17 (15)
N6—N5—C27	118.85 (12)	C23—C24—C25	127.93 (14)
N5—N6—C26	108.04 (12)	C25—C24—C26	107.76 (14)
C22—N4—H4A	116.0 (12)	N5—C25—C24	105.83 (13)
C23—N4—H4A	116.0 (12)	O5—C25—N5	124.06 (15)
N5—N6—H6	116.1 (12)	O5—C25—C24	130.11 (15)
C26—N6—H6	119.1 (11)	N6—C26—C24	107.70 (14)
O1—C1—C2	124.32 (15)	O6—C26—C24	128.32 (16)
O1—C1—C6	116.43 (15)	O6—C26—N6	123.98 (14)
C2—C1—C6	119.25 (15)	N5—C27—C28	119.95 (14)
C1—C2—C3	119.97 (16)	C28—C27—C32	119.75 (16)
C2—C3—C4	120.71 (16)	N5—C27—C32	120.29 (14)
C3—C4—C5	119.95 (16)	C27—C28—C29	119.51 (16)
C4—C5—C6	119.72 (16)	C28—C29—C30	121.06 (17)
C1—C6—C5	120.38 (15)	C29—C30—C31	119.12 (16)
N1—C6—C1	115.82 (14)	C30—C31—C32	120.86 (16)
N1—C6—C5	123.78 (14)	C27—C32—C31	119.69 (15)
N1—C7—C8	121.87 (15)	C19—C18—H18	120.00
C7—C8—C10	124.68 (15)	C17—C18—H18	120.00
C9—C8—C10	108.23 (14)	C18—C19—H19	120.00
C7—C8—C9	126.77 (16)	C20—C19—H19	120.00
N2—C9—C8	105.69 (14)	C19—C20—H20	120.00
O2—C9—N2	124.45 (14)	C21—C20—H20	120.00
O2—C9—C8	129.85 (16)	C22—C21—H21	120.00
N3—C10—C8	107.75 (13)	C20—C21—H21	120.00
O3—C10—C8	128.75 (15)	C24—C23—H23	119.00
O3—C10—N3	123.49 (15)	N4—C23—H23	119.00
N2—C11—C16	119.35 (14)	C27—C28—H28	120.00
N2—C11—C12	121.03 (15)	C29—C28—H28	120.00
C12—C11—C16	119.60 (15)	C28—C29—H29	119.00
C11—C12—C13	119.25 (16)	C30—C29—H29	119.00
C12—C13—C14	121.64 (16)	C31—C30—H30	120.00
C13—C14—C15	118.67 (16)	C29—C30—H30	120.00
C14—C15—C16	121.10 (16)	C30—C31—H31	120.00
C11—C16—C15	119.73 (16)	C32—C31—H31	120.00
C1—C2—H2	120.00	C27—C32—H32	120.00
C3—C2—H2	120.00	C31—C32—H32	120.00
C2—C3—H3	120.00	S1—C33—H33A	109.00
C4—C3—H3	120.00	S1—C33—H33B	109.00
C5—C4—H4	120.00	S1—C33—H33C	109.00
C3—C4—H4	120.00	H33A—C33—H33B	109.00
C6—C5—H5	120.00	H33A—C33—H33C	109.00
C4—C5—H5	120.00	H33B—C33—H33C	109.00
C8—C7—H7	119.00	S1—C34—H34A	109.00
N1—C7—H7	119.00	S1—C34—H34B	110.00
C13—C12—H12	120.00	S1—C34—H34C	109.00
C11—C12—H12	120.00	H34A—C34—H34B	110.00
C14—C13—H13	119.00	H34A—C34—H34C	109.00
C12—C13—H13	119.00	H34B—C34—H34C	109.00
C13—C14—H14	121.00

C6—N1—C7—C8	−174.14 (15)	C7—C8—C9—N2	−172.41 (15)
C7—N1—C6—C5	5.4 (2)	C10—C8—C9—O2	−177.61 (16)
C7—N1—C6—C1	−176.59 (15)	C7—C8—C10—O3	−3.3 (3)
C9—N2—C11—C12	−18.0 (2)	C7—C8—C10—N3	175.97 (15)
C11—N2—N3—C10	171.57 (13)	C7—C8—C9—O2	8.7 (3)
C11—N2—C9—O2	10.8 (3)	C9—C8—C10—O3	−177.15 (17)
N3—N2—C11—C16	0.8 (2)	C9—C8—C10—N3	2.08 (18)
C9—N2—C11—C16	163.72 (15)	N2—C11—C16—C15	177.38 (15)
C9—N2—N3—C10	5.64 (17)	C12—C11—C16—C15	−0.9 (2)
C11—N2—C9—C8	−168.25 (14)	N2—C11—C12—C13	−177.88 (14)
N3—N2—C11—C12	179.05 (14)	C16—C11—C12—C13	0.4 (2)
N3—N2—C9—O2	174.78 (15)	C11—C12—C13—C14	0.4 (2)
N3—N2—C9—C8	−4.22 (16)	C12—C13—C14—C15	−0.7 (3)
N2—N3—C10—C8	−4.60 (17)	C13—C14—C15—C16	0.1 (3)
N2—N3—C10—O3	174.69 (15)	C14—C15—C16—C11	0.7 (3)
C23—N4—C22—C17	−171.75 (16)	O4—C17—C22—C21	179.01 (16)
C22—N4—C23—C24	179.09 (16)	C18—C17—C22—N4	179.75 (16)
C23—N4—C22—C21	9.1 (3)	O4—C17—C22—N4	−0.2 (2)
N6—N5—C27—C28	174.88 (15)	O4—C17—C18—C19	−179.90 (17)
N6—N5—C27—C32	−4.1 (2)	C22—C17—C18—C19	0.2 (3)
C27—N5—C25—C24	−175.58 (15)	C18—C17—C22—C21	−1.1 (3)
N6—N5—C25—O5	174.60 (15)	C17—C18—C19—C20	0.5 (3)
C25—N5—C27—C28	−15.0 (3)	C18—C19—C20—C21	−0.4 (3)
C27—N5—C25—O5	3.8 (3)	C19—C20—C21—C22	−0.5 (3)
C25—N5—C27—C32	166.08 (16)	C20—C21—C22—C17	1.2 (3)
C27—N5—N6—C26	179.47 (14)	C20—C21—C22—N4	−179.68 (16)
C25—N5—N6—C26	7.45 (17)	N4—C23—C24—C26	1.5 (3)
N6—N5—C25—C24	−4.77 (17)	N4—C23—C24—C25	176.69 (16)
N5—N6—C26—O6	172.99 (15)	C26—C24—C25—N5	0.50 (18)
N5—N6—C26—C24	−6.87 (18)	C23—C24—C26—O6	0.2 (3)
C2—C1—C6—N1	−176.10 (14)	C23—C24—C26—N6	−179.97 (16)
O1—C1—C6—N1	4.4 (2)	C25—C24—C26—O6	−175.85 (17)
O1—C1—C6—C5	−177.50 (15)	C25—C24—C26—N6	4.01 (19)
C6—C1—C2—C3	−0.9 (2)	C23—C24—C25—O5	5.4 (3)
O1—C1—C2—C3	178.54 (16)	C23—C24—C25—N5	−175.32 (17)
C2—C1—C6—C5	2.0 (2)	C26—C24—C25—O5	−178.81 (17)
C1—C2—C3—C4	−0.7 (3)	N5—C27—C28—C29	179.85 (15)
C2—C3—C4—C5	1.2 (3)	C32—C27—C28—C29	−1.2 (3)
C3—C4—C5—C6	−0.1 (3)	N5—C27—C32—C31	179.89 (16)
C4—C5—C6—N1	176.44 (15)	C28—C27—C32—C31	0.9 (3)
C4—C5—C6—C1	−1.5 (2)	C27—C28—C29—C30	0.5 (3)
N1—C7—C8—C10	6.4 (2)	C28—C29—C30—C31	0.4 (3)
N1—C7—C8—C9	179.11 (15)	C29—C30—C31—C32	−0.7 (3)
C10—C8—C9—N2	1.32 (17)	C30—C31—C32—C27	0.0 (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···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (2)	2.23 (2)	2.6235 (18)	107 (2)
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···O4	0.88 (2)	2.19 (2)	2.6019 (18)	109 (2)
N4—H4A···O6	0.88 (2)	2.11 (2)	2.8050 (18)	136 (2)
O4—H4B···S1ⁱⁱ	0.85 (2)	2.85 (2)	3.5767 (14)	145 (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)
C7—H7···O3^iv	0.95	2.40	3.055 (2)	126
C12—H12···O2	0.95	2.27	2.897 (2)	122
C16—H16···N3	0.95	2.42	2.775 (2)	102
C28—H28···O5	0.95	2.27	2.893 (2)	123
C32—H32···N6	0.95	2.46	2.801 (2)	101
C34—H34B···O3^v	0.98	2.43	3.403 (3)	175
C29—H29···Cg3^vi	0.95	2.64	3.548 (2)	160
C33—H33C···Cg6^iv	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, z; (v) x−1, 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···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.863 (18)	2.154 (19)	2.8265 (17)	134.5 (17)
O1—H1A···O5	0.85 (2)	1.80 (2)	2.6479 (17)	174 (2)
N3—H3A···O2ⁱ	0.875 (18)	1.902 (18)	2.7740 (17)	174 (2)
N4—H4A···O6	0.877 (17)	2.109 (19)	2.8050 (18)	135.8 (15)
O4—H4B···S1ⁱⁱ	0.85 (2)	2.846 (19)	3.5767 (14)	144.7 (19)
O4—H4B···O7ⁱⁱ	0.85 (2)	1.76 (2)	2.6061 (18)	172 (2)
N6—H6···O6ⁱⁱⁱ	0.880 (17)	1.915 (18)	2.7831 (19)	168.6 (17)
C34—H34B···O3^iv	0.98	2.43	3.403 (3)	175
C29—H29···Cg3^v	0.95	2.64	3.548 (2)	160
C33—H33C···Cg6^vi	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.

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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