1-((E)-{2-[4-(2-{(1E)-[(carbamo­thioyl­amino)­imino]­meth­yl}phen­oxy)but­oxy]benzyl­idene}amino)­thio­urea dimethyl sulfoxide disolvate

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Abdel-Raheem, E.M.M.; Albayati, M.R.

doi:10.1107/S2414314616009469

organic compounds

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ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160946

doi:10.1107/S2414314616009469

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1-((E)-{2-[4-(2-{(1E)-[(carbamothioylamino)imino]methyl}phenoxy)butoxy]benzylidene}amino)thiourea dimethyl sulfoxide disolvate

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Eman M. M. Abdel-Raheem ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Sohag University, 82524-Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by P. C. Healy, Griffith University, Australia (Received 9 June 2016; accepted 11 June 2016; online 17 June 2016)

The title compound, C₂₀H₂₄N₆O₂S₂·2C₂H₆OS, has crystallographically imposed centrosymmetry. The packing is assisted by N—H⋯O, C—H⋯O and N—H⋯S interactions with the lattice solvent molecules, forming a two-dimensional network parallel to (1-10). The lattice dimethyl sulfoxide molecules (except for the S atoms) were modelled over two sites with refined occupancies of 0.831 (3):0.169 (3).

Keywords: crystal structure; bis(dimethylsulfoxide) solvate; thiourea.

CCDC reference: 1484676

Structure description

Thiosemicarbazones and their metal complexes have been known and interest to chemists for over fifty years due to their wide spectrum of biological activity such as antitumor, antibiotic and antiviral properties (Adelstein, 1973 ; Pandeya & Dimmock, 1993 ; Quiroga, et al., 1998 ; Christlieb & Dilworth, 2006 ). The synthesis of bis functionalized compounds are considered as significant precursors for building blocks of vital molecules such as nanoscience and supramolecular chemistry (Holland et al., 2007 ), and binucleating ligand designs (Gavrilova & Bosnich, 2004 ). In this context we report in this study the synthesis and crystal structure of the title compound.

The title molecule (Fig. 1) has crystallographically imposed centrosymmetry. In the crystal, the packing is assisted by N—H⋯O, C—H⋯O and N—H⋯S interactions with the lattice DMSO molecules (Table 1 and Fig. 2), forming a two-dimensional network parallel to (1 $[\overlone1]$ 0)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1ⁱ	0.91	2.49	3.371 (2)	163
N3—H3A⋯O2	0.91	2.14	2.887 (3)	139
N3—H3B⋯O2ⁱⁱ	0.91	2.04	2.885 (3)	153
C7—H7B⋯O2ⁱⁱⁱ	0.99	2.49	3.471 (3)	174
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y+1, -z; (iii) -x+1, -y+1, -z+1.

Figure 1
The title molecule, showing the atom-labeling scheme and 50% probability displacement ellipsoids [symmetry code: (i) −x, −y, 1 − z].

Figure 2
Packing viewed down the a axis. Intermolecular N—H⋯O, C—H⋯O and N—H⋯S hydrogen bonds are shown, respectively, as blue, black and purple dotted lines.

Synthesis and crystallization

Salicyldehyde 122 mg (1 mmol) in hot ethanolic potassium hydroxide solution (prepared by dissolving 56 mg (1 mmol) of KOH in 10 ml of absolute ethanol) was stirred until a clear solution was obtained. The solution was evaporated under vacuum and the residue was dissolved in 5 ml DMF and then 119.4 µl (0.5 mmol) of 1,4-dibromobutane was added. The reaction mixture was refluxed for 5 minutes. The resulted potassium bromide was separated by filtration and the filtrate was then evaporated under vacuum. The remaining solid was washed with water and crystallized from ethanol to give high quality crystals (m.p. 513 K) suitable for X-ray analysis in a good yield (90%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The lattice DMSO molecules (except S atoms) were modelled over two sites with refined occupancies of 0.831 (3):0.169 (3).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₂₄N₆O₂S₂·2C₂H₆OS
M_r	600.83
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	7.2571 (2), 9.7909 (2), 12.0060 (2)
α, β, γ (°)	112.984 (1), 98.163 (1), 96.909 (1)
V (Å³)	762.80 (3)
Z	1
Radiation type	Cu Kα
μ (mm⁻¹)	3.19
Crystal size (mm)	0.24 × 0.15 × 0.09

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2015 )
T_min, T_max	0.65, 0.76
No. of measured, independent and observed [I > 2σ(I)] reflections	8374, 2932, 2679
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.162, 1.08
No. of reflections	2932
No. of parameters	183
No. of restraints	27
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.68
Computer programs: APEX2 and SAINT (Bruker, 2015), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1484676

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616009469/hg4009sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616009469/hg4009Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616009469/hg4009Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1-((E)-{2-[4-(2-{(1E)-[(Carbamothioylamino)imino]methyl}phenoxy)butoxy]benzylidene}amino)thiourea dimethyl sulfoxide disolvate top

Crystal data top

C₂₀H₂₄N₆O₂S₂·2C₂H₆OS	Z = 1
M_r = 600.83	F(000) = 318
Triclinic, P1	D_x = 1.308 Mg m⁻³
a = 7.2571 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.7909 (2) Å	Cell parameters from 6799 reflections
c = 12.0060 (2) Å	θ = 4.1–72.1°
α = 112.984 (1)°	µ = 3.19 mm⁻¹
β = 98.163 (1)°	T = 150 K
γ = 96.909 (1)°	Thick plate, colourless
V = 762.80 (3) Å³	0.24 × 0.15 × 0.09 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2932 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2679 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.1°, θ_min = 5.0°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −12→11
T_min = 0.65, T_max = 0.76	l = −14→14
8374 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.0905P)² + 0.766P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.002
2932 reflections	Δρ_max = 0.88 e Å⁻³
183 parameters	Δρ_min = −0.68 e Å⁻³
27 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (13)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) while those attached to nitrogen were placed in locations derived from a difference map and their parameters adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.18022 (10)	0.04286 (7)	−0.12107 (6)	0.0368 (2)
O1	0.1735 (3)	0.2497 (2)	0.51184 (15)	0.0357 (4)
N1	0.2228 (3)	0.3358 (2)	0.22135 (18)	0.0304 (5)
N2	0.1727 (3)	0.2071 (2)	0.11133 (19)	0.0332 (5)
H2A	0.0875	0.1248	0.1011	0.040*
N3	0.3466 (3)	0.3281 (3)	0.0209 (2)	0.0390 (5)
H3A	0.3769	0.4102	0.0950	0.047*
H3B	0.3708	0.3273	−0.0516	0.047*
C1	0.2179 (3)	0.4002 (3)	0.5403 (2)	0.0300 (5)
C2	0.2562 (4)	0.5137 (3)	0.6594 (2)	0.0370 (6)
H2	0.2490	0.4888	0.7279	0.044*
C3	0.3048 (4)	0.6632 (3)	0.6779 (3)	0.0411 (7)
H3	0.3303	0.7408	0.7593	0.049*
C4	0.3165 (4)	0.7009 (3)	0.5790 (3)	0.0431 (7)
H4	0.3500	0.8038	0.5926	0.052*
C5	0.2792 (4)	0.5879 (3)	0.4600 (3)	0.0378 (6)
H5	0.2889	0.6139	0.3923	0.045*
C6	0.2279 (3)	0.4369 (3)	0.4385 (2)	0.0284 (5)
C7	0.1356 (4)	0.2043 (3)	0.6080 (2)	0.0372 (6)
H7A	0.0272	0.2458	0.6410	0.045*
H7B	0.2480	0.2418	0.6766	0.045*
C8	0.0894 (4)	0.0336 (3)	0.5507 (2)	0.0383 (6)
H8A	0.0738	−0.0015	0.6164	0.046*
H8B	0.1978	−0.0051	0.5157	0.046*
C9	0.1840 (3)	0.3150 (3)	0.3144 (2)	0.0297 (5)
H9	0.1248	0.2170	0.3027	0.036*
C10	0.2385 (4)	0.2042 (3)	0.0115 (2)	0.0301 (5)
S2	0.29091 (12)	0.73336 (10)	0.18388 (10)	0.0576 (3)
O2	0.4525 (3)	0.6510 (2)	0.16444 (18)	0.0268 (5)	0.831 (3)
C11	0.3689 (11)	0.9102 (8)	0.2855 (8)	0.114 (2)	0.831 (3)
H11A	0.2621	0.9631	0.2976	0.172*	0.831 (3)
H11B	0.4297	0.9117	0.3644	0.172*	0.831 (3)
H11C	0.4612	0.9606	0.2549	0.172*	0.831 (3)
C12	0.2625 (10)	0.7934 (10)	0.0557 (7)	0.101 (2)	0.831 (3)
H12A	0.1582	0.8491	0.0607	0.151*	0.831 (3)
H12B	0.3802	0.8588	0.0617	0.151*	0.831 (3)
H12C	0.2338	0.7041	−0.0233	0.151*	0.831 (3)
O2A	0.0956 (8)	0.6372 (9)	0.1245 (8)	0.0268 (5)	0.169 (3)
C11A	0.207 (5)	0.760 (4)	0.310 (2)	0.114 (2)	0.169 (3)
H11D	0.3039	0.8269	0.3829	0.172*	0.169 (3)
H11E	0.0943	0.8055	0.3075	0.172*	0.169 (3)
H11F	0.1722	0.6622	0.3142	0.172*	0.169 (3)
C12A	0.334 (5)	0.907 (3)	0.158 (4)	0.101 (2)	0.169 (3)
H12D	0.4631	0.9624	0.1997	0.151*	0.169 (3)
H12E	0.3171	0.8803	0.0693	0.151*	0.169 (3)
H12F	0.2430	0.9705	0.1919	0.151*	0.169 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0455 (4)	0.0330 (4)	0.0280 (4)	−0.0013 (3)	0.0110 (3)	0.0099 (3)
O1	0.0514 (11)	0.0308 (9)	0.0257 (8)	0.0010 (8)	0.0113 (8)	0.0135 (7)
N1	0.0320 (11)	0.0314 (10)	0.0261 (10)	0.0012 (8)	0.0052 (8)	0.0117 (8)
N2	0.0401 (12)	0.0296 (10)	0.0274 (10)	−0.0034 (9)	0.0081 (9)	0.0118 (9)
N3	0.0461 (13)	0.0339 (11)	0.0339 (11)	−0.0024 (10)	0.0159 (10)	0.0111 (9)
C1	0.0280 (12)	0.0319 (12)	0.0297 (12)	0.0047 (10)	0.0065 (9)	0.0126 (10)
C2	0.0378 (14)	0.0398 (14)	0.0296 (13)	0.0060 (11)	0.0068 (10)	0.0110 (11)
C3	0.0386 (14)	0.0357 (14)	0.0353 (14)	0.0084 (11)	0.0011 (11)	0.0025 (11)
C4	0.0475 (16)	0.0275 (13)	0.0458 (16)	0.0069 (12)	−0.0012 (13)	0.0101 (12)
C5	0.0405 (15)	0.0322 (13)	0.0400 (14)	0.0051 (11)	0.0002 (11)	0.0176 (11)
C6	0.0266 (12)	0.0299 (12)	0.0288 (12)	0.0056 (9)	0.0046 (9)	0.0127 (10)
C7	0.0448 (15)	0.0438 (15)	0.0241 (12)	0.0005 (12)	0.0049 (10)	0.0184 (11)
C8	0.0464 (16)	0.0416 (14)	0.0301 (13)	0.0015 (12)	0.0018 (12)	0.0223 (12)
C9	0.0306 (12)	0.0293 (12)	0.0292 (12)	0.0025 (10)	0.0052 (9)	0.0134 (10)
C10	0.0306 (12)	0.0329 (12)	0.0293 (12)	0.0040 (10)	0.0071 (9)	0.0159 (10)
S2	0.0506 (5)	0.0574 (5)	0.0882 (7)	0.0202 (4)	0.0388 (4)	0.0433 (5)
O2	0.0279 (10)	0.0273 (10)	0.0312 (10)	0.0059 (8)	0.0099 (8)	0.0171 (8)
C11	0.109 (5)	0.077 (4)	0.140 (6)	0.023 (3)	0.055 (4)	0.014 (4)
C12	0.085 (4)	0.144 (5)	0.127 (5)	0.054 (4)	0.036 (4)	0.098 (4)
O2A	0.0279 (10)	0.0273 (10)	0.0312 (10)	0.0059 (8)	0.0099 (8)	0.0171 (8)
C11A	0.109 (5)	0.077 (4)	0.140 (6)	0.023 (3)	0.055 (4)	0.014 (4)
C12A	0.085 (4)	0.144 (5)	0.127 (5)	0.054 (4)	0.036 (4)	0.098 (4)

Geometric parameters (Å, º) top

S1—C10	1.700 (3)	C7—H7B	0.9900
O1—C1	1.360 (3)	C8—C8ⁱ	1.523 (5)
O1—C7	1.438 (3)	C8—H8A	0.9900
N1—C9	1.274 (3)	C8—H8B	0.9900
N1—N2	1.385 (3)	C9—H9	0.9500
N2—C10	1.343 (3)	S2—O2	1.496 (2)
N2—H2A	0.9101	S2—O2A	1.508 (4)
N3—C10	1.319 (3)	S2—C11	1.651 (7)
N3—H3A	0.9100	S2—C11A	1.651 (8)
N3—H3B	0.9101	S2—C12A	1.841 (7)
C1—C2	1.389 (4)	S2—C12	1.844 (6)
C1—C6	1.411 (3)	C11—H11A	0.9800
C2—C3	1.385 (4)	C11—H11B	0.9800
C2—H2	0.9500	C11—H11C	0.9800
C3—C4	1.384 (4)	C12—H12A	0.9800
C3—H3	0.9500	C12—H12B	0.9800
C4—C5	1.387 (4)	C12—H12C	0.9800
C4—H4	0.9500	C11A—H11D	0.9800
C5—C6	1.390 (4)	C11A—H11E	0.9800
C5—H5	0.9500	C11A—H11F	0.9800
C6—C9	1.460 (3)	C12A—H12D	0.9800
C7—C8	1.510 (4)	C12A—H12E	0.9800
C7—H7A	0.9900	C12A—H12F	0.9800

C1—O1—C7	118.3 (2)	H8A—C8—H8B	107.7
C9—N1—N2	114.0 (2)	N1—C9—C6	122.0 (2)
C10—N2—N1	120.4 (2)	N1—C9—H9	119.0
C10—N2—H2A	117.1	C6—C9—H9	119.0
N1—N2—H2A	122.4	N3—C10—N2	118.0 (2)
C10—N3—H3A	119.0	N3—C10—S1	122.66 (19)
C10—N3—H3B	115.2	N2—C10—S1	119.34 (18)
H3A—N3—H3B	125.2	O2—S2—C11	110.1 (3)
O1—C1—C2	124.6 (2)	O2A—S2—C11A	81.0 (14)
O1—C1—C6	115.2 (2)	O2A—S2—C12A	114.8 (11)
C2—C1—C6	120.2 (2)	C11A—S2—C12A	112.6 (17)
C3—C2—C1	119.7 (3)	O2—S2—C12	103.4 (2)
C3—C2—H2	120.2	C11—S2—C12	91.0 (4)
C1—C2—H2	120.2	S2—C11—H11A	109.5
C4—C3—C2	120.7 (3)	S2—C11—H11B	109.5
C4—C3—H3	119.6	H11A—C11—H11B	109.5
C2—C3—H3	119.6	S2—C11—H11C	109.5
C3—C4—C5	119.8 (3)	H11A—C11—H11C	109.5
C3—C4—H4	120.1	H11B—C11—H11C	109.5
C5—C4—H4	120.1	S2—C12—H12A	109.5
C4—C5—C6	120.7 (3)	S2—C12—H12B	109.5
C4—C5—H5	119.6	H12A—C12—H12B	109.5
C6—C5—H5	119.6	S2—C12—H12C	109.5
C5—C6—C1	118.9 (2)	H12A—C12—H12C	109.5
C5—C6—C9	122.4 (2)	H12B—C12—H12C	109.5
C1—C6—C9	118.8 (2)	S2—C11A—H11D	109.5
O1—C7—C8	106.9 (2)	S2—C11A—H11E	109.5
O1—C7—H7A	110.3	H11D—C11A—H11E	109.5
C8—C7—H7A	110.3	S2—C11A—H11F	109.5
O1—C7—H7B	110.3	H11D—C11A—H11F	109.5
C8—C7—H7B	110.3	H11E—C11A—H11F	109.5
H7A—C7—H7B	108.6	S2—C12A—H12D	109.5
C7—C8—C8ⁱ	113.8 (3)	S2—C12A—H12E	109.5
C7—C8—H8A	108.8	H12D—C12A—H12E	109.5
C8ⁱ—C8—H8A	108.8	S2—C12A—H12F	109.5
C7—C8—H8B	108.8	H12D—C12A—H12F	109.5
C8ⁱ—C8—H8B	108.8	H12E—C12A—H12F	109.5

C9—N1—N2—C10	−166.5 (2)	C2—C1—C6—C5	1.0 (4)
C7—O1—C1—C2	9.7 (4)	O1—C1—C6—C9	2.2 (3)
C7—O1—C1—C6	−171.7 (2)	C2—C1—C6—C9	−179.1 (2)
O1—C1—C2—C3	178.3 (2)	C1—O1—C7—C8	179.6 (2)
C6—C1—C2—C3	−0.2 (4)	O1—C7—C8—C8ⁱ	−63.5 (4)
C1—C2—C3—C4	−0.3 (4)	N2—N1—C9—C6	179.4 (2)
C2—C3—C4—C5	0.0 (5)	C5—C6—C9—N1	13.0 (4)
C3—C4—C5—C6	0.8 (4)	C1—C6—C9—N1	−166.9 (2)
C4—C5—C6—C1	−1.3 (4)	N1—N2—C10—N3	−1.9 (4)
C4—C5—C6—C9	178.8 (2)	N1—N2—C10—S1	178.10 (18)
O1—C1—C6—C5	−177.7 (2)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1ⁱⁱ	0.91	2.49	3.371 (2)	163
N3—H3A···O2	0.91	2.14	2.887 (3)	139
N3—H3B···O2ⁱⁱⁱ	0.91	2.04	2.885 (3)	153
C7—H7B···O2^iv	0.99	2.49	3.471 (3)	174

Symmetry codes: (ii) −x, −y, −z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1.

Acknowledgements

The support of NSF-MRI Grant #1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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