(E)-2-(3-Cinnamoyl­thio­ureido)acetic acid dimethyl sulfoxide disolvate

Ibrahim N Hassan; Wan Ramli Wan Daud; Bohari M Yamin; Mohammad B Kassim

doi:10.1107/S1600536811036750

. 2011 Sep 17;67(Pt 10):o2686. doi: 10.1107/S1600536811036750

(E)-2-(3-Cinnamoylthioureido)acetic acid dimethyl sulfoxide disolvate

Ibrahim N Hassan ^a,^*, Wan Ramli Wan Daud ^b,^a, Bohari M Yamin ^c, Mohammad B Kassim ^c,^a

PMCID: PMC3201284 PMID: 22058788

Abstract

In the title compound, C₁₂H₁₂N₂O₃S·2C₂H₆OS, the acetic acid and cinnamoyl groups adopt Z and E configurations, respectively, with respect to the thio group about the C—N bonds. The components of the asymmetric unit are connected by N—H⋯O and O—H⋯O hydrogen bonds and in the crystal weak intermolecular C—H⋯O and C—H⋯S hydrogen bonds further connect the components into chains along the b axis. In the main molecule, an intramolecular N—H⋯O hydrogen bond is also present.

Related literature

For related structures, see: Hassan et al. (2009 ▶, 2010a ▶,b ▶,c ▶, 2011 ▶); Nasir et al. (2011 ▶). For the synthesis, see: Hassan et al. (2008 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₂H₁₂N₂O₃S·2C₂H₆OS
M _r = 420.55
Triclinic,
a = 7.327 (3) Å
b = 12.064 (5) Å
c = 13.691 (6) Å
α = 65.794 (8)°
β = 75.603 (9)°
γ = 85.484 (9)°
V = 1068.6 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 298 K
0.42 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.859, T _max = 0.936
10964 measured reflections
3774 independent reflections
2650 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.085
wR(F ²) = 0.251
S = 1.06
3774 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036750/lh5324sup1.cif

e-67-o2686-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036750/lh5324Isup2.hkl

e-67-o2686-Isup2.hkl^{(185KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036750/lh5324Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5	0.86	2.02	2.867 (5)	167
N2—H2A⋯O1	0.86	1.94	2.625 (4)	136
O3—H3A⋯O4	0.82	1.76	2.562 (5)	166
C14—H14C⋯O2	0.96	2.54	3.423 (8)	153
C14—H14A⋯O5ⁱ	0.96	2.43	3.319 (7)	154
C15—H15B⋯O4ⁱⁱ	0.96	2.58	3.468 (7)	153
C16—H16B⋯S1ⁱⁱⁱ	0.96	2.85	3.702 (7)	148

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank Universiti Kebangsaan Malaysia for providing facilities and grants (postdoctoral for INH, UKM-GUP-BTT-07–30-190 and UKM-OUP-TK-16–73/2010&2011) and the Kementerian Pengajian Tinggi, Malaysia, for the research fund No. UKM-ST-06-FRGS0111–2009.

supplementary crystallographic information

Comment

The title compound (I) is the thiourea carboxylic acid version of our previously reported ester molecules (E)-methyl-2-(3-cinnamoylthioureido)acetate (II) (Hassan et al., 2010a)and (E)-ethyl-2-(3- cinnmoylthioureido)acetate (III) (Hassan et al., 2010b) and analogous to methyl-2-(3-benzoylthioureido)acetate (IV) (Hassan et al., 2009). The molecule maintains the same E-Z configuration with respect to the positions of the acetic acid and cinnamoyl groups, relative to the S atom across the C—N bonds, respectively (Fig. 1). In general, the bond lengths (Allen et al., 1987) and angles in (I) are in normal ranges and comparable to those in (II), (III) and (IV). The the C═S bond length [1.665 (4) Å] is the same within experimental error to that in (II) [1.666 (3) Å] and that of (III) [1.656 (5) Å]. The C7═C8 bond length [1.331 (6) Å] is slightly longer than that reported by Hassan et al. (2010c) [1.320 (3) Å]. The carbonyl C═O bond length [1.215 (5) Å] is the same within experimental error to that reported by Nasir et al. (2011) [1.213 (3) Å]. The S1/O1/O2/N1/N2/C1—C12 fragment is essentially planar with a maximum deviation of 0.043 (5) Å, for atom C7. In the crystal, the components of the asymmtric unit are connected by N—H···O and O—H···O hydrogen bonds and weak intermolecular C—H···O and C—H···S hydrogen bonds connect the components into one-dimensional chains along the b axis (Fig. 2). In the main molecule an intramolecular N—H···O hydrogen bond is also present.

Experimental

The title compound was synthesized according to a previously reported method (Hassan et al., 2008). A yellowish crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from CH₂Cl₂ solution at room temperature (yield 79%).