N-[Eth­yl(2-hy­droxy­eth­yl)carbamo­thio­yl]-3-fluoro­benzamide

Nor Wahida Awang; Siti Aishah Hasbullah; Siti Fairus M Yusoff; Bohari M Yamin

doi:10.1107/S1600536814008174

. 2014 Apr 18;70(Pt 5):o570. doi: 10.1107/S1600536814008174

N-[Ethyl(2-hydroxyethyl)carbamothioyl]-3-fluorobenzamide

Nor Wahida Awang ^a, Siti Aishah Hasbullah ^a, Siti Fairus M Yusoff ^a,^*, Bohari M Yamin ^b

PMCID: PMC4011211 PMID: 24860375

Abstract

In the title compound, C₁₂H₁₅FN₂O₂S, the molecule adopts a cis configuration of the fluorobenzoyl group with respect to the thiono group about their C—N bond. The dihedral angle between the fluorobenzoyl group and the thiourea N₂CS fragment is 69.60 (11)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules form chains along the b-axis direction via O—H⋯S and C—H⋯O hydrogen bonds.

Related literature

For bond length data see: Allen et al. (1987 ▶). For a related structure, see: Yamin et al. (2014 ▶). graphic file with name e-70-0o570-scheme1.jpg

Experimental

Crystal data

C₁₂H₁₅FN₂O₂S
M _r = 270.32
Orthorhombic,
a = 6.0205 (3) Å
b = 12.9441 (6) Å
c = 17.1071 (9) Å
V = 1333.16 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.50 × 0.50 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.885, T _max = 0.931
21708 measured reflections
3290 independent reflections
2864 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.086
S = 1.07
3290 reflections
168 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ▶), 1378 Friedel pairs
Absolute structure parameter: −0.05 (8)

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: 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/S1600536814008174/bq2395sup1.cif

e-70-0o570-sup1.cif^{(22.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008174/bq2395Isup2.hkl

e-70-0o570-Isup2.hkl^{(161.4KB, hkl)}

Click here for additional data file.^{(4.9KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814008174/bq2395Isup3.cml

CCDC reference: 996752

Additional supporting information: 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⋯O2	0.86	2.03	2.805 (2)	150
O2—H2A⋯S1ⁱ	0.82 (3)	2.49 (3)	3.2805 (19)	166 (3)
C11—H11B⋯O1ⁱⁱ	0.97	2.44	3.259 (3)	142

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

Acknowledgments

The authors would like to thank Universiti Kebangsaan Malaysia for research grants DLP-2013–009 and DIP-2012–11. Research facilities provided by the Centre of Research and Instrumentation (CRIM) is very much appreciated.

supplementary crystallographic information

1. Comment

The expected cis configuration of the carbonoyl with respect to the thione group was observed when one terminal of the thiourea moiety is a secondary amine as in the case of 2,4-dichloro-N-[ethyl(2-hydroxyethyl)- carbamothioyl]benzamide (Yamin et al., 2014). Such configuration will enhance its property as bidentate ligand in a complexation reaction with metals. The title compound is similar but having a monosubstituted flourine atom at position-3 of the benzene ring (Fig 1). The fluorobenzoyl group is also cis to the thiono group, C8—S1 about the N1—C8 bond. The thiourea moiety S1/N1/N2/C8 and fluorobenzene ring F1/(C1—C6) are planar with maximum deviation of 0.022 (2) Å for C8 atom from the least square plane of the thiourea moiety fragment. The two planes make dihedral angle of 69.60 (11)°, slightly less than that of the analog (75.41 (8)°). The bond lengths and angles are in normal ranges (Allen et al., 1987). There is intramolecular hydrogen bond between hydroxyl oxygen atom, (O2) and the hydrogen of the amide group. In the crystal structure, molecules are linked by O2—H2A···S1 and C11—H11B···O1 intermolecular hydrogen bonds (see Table 1 for symmetry codes) to form one-dimensional chain along the b axis (Fig.2).

2. Experimental

A mixture of acetone (30 ml) solution and 2-(ethylamino)ethanol (0.18 g, 2 mmol) was added into round-bottom flask containing 4-fluorobenzoyl isothiocyanate (0.36 g, 2 mmol). The mixture was refluxed for 3 h. The mixture then cooled and filtered off. The filtrate was left to evaporate at room temperature. The solid formed was washed with water and cold ethanol. Crystals suitable for X-ray study were obtained by recrystallization from ethanol.