Crystal stucture of methyl 2-({[2-(meth­oxy­carbon­yl)phen­yl]carbamo­yl}amino)­benzoate

Hasna Yassine; Mostafa Khouili; Lahcen El Ammari; Mohamed Saadi; El Mostafa Ketatni

doi:10.1107/S2056989015006465

. 2015 Apr 9;71(Pt 5):o297–o298. doi: 10.1107/S2056989015006465

Crystal stucture of methyl 2-({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)benzoate

Hasna Yassine ^a, Mostafa Khouili ^a,^*, Lahcen El Ammari ^b, Mohamed Saadi ^b, El Mostafa Ketatni ^c

PMCID: PMC4420073 PMID: 25995913

Abstract

In the title compound, C₁₇H₁₆N₂O₅, the dihedral angles between the central urea [N—C(=O)—N] fragment and its attached benzene rings are 20.20 (14) and 24.24 (13)°; the dihedral angle between the aromatic rings is 42.1 (1)°. The molecular conformation is consolidated by two intramolecular N—H⋯O hydrogen bonds, which both generate S(6) rings. In the crystal, inversion dimers linked by pairs of C—H⋯O interactions generate R ₂ ²(14) loops. The dimers are linked by further C—H⋯O interactions into (011) sheets.

Keywords: crystal structure, urea derivative, hydrogen bonding

Related literature

For the medical and biological activities of urea derivatives, see: Abad et al. (2004 ▸); Chen et al. (2005 ▸); Batra et al. (2006 ▸). For cytokinin activity, see: Wang et al. (2001 ▸); Ricci et al. (2005 ▸).

Experimental

Crystal data

C₁₇H₁₆N₂O₅
M _r = 328.32
Monoclinic,
a = 9.005 (8) Å
b = 23.80 (2) Å
c = 7.400 (7) Å
β = 93.66 (4)°
V = 1583 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.42 × 0.36 × 0.29 mm

Data collection

Bruker X8 APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.693, T _max = 0.747
11500 measured reflections
3364 independent reflections
1667 reflections with I > 2σ(I)
R _int = 0.066

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.137
S = 0.95
3364 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015006465/hb7393sup1.cif

e-71-0o297-sup1.cif^{(25KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006465/hb7393Isup2.hkl

e-71-0o297-Isup2.hkl^{(165KB, hkl)}

Click here for additional data file.^{(6.2KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015006465/hb7393Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015006465/hb7393fig1.tif

A view of the molecule of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.^{(1.5MB, tif)}

. DOI: 10.1107/S2056989015006465/hb7393fig2.tif

Part of the crystal structure of the title compound, showing hydrogen-bonded (dashed lines) dimers.

CCDC reference: 1056943

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N2H2NO5	0.86	1.96	2.677(3)	140
N3H3NO2	0.86	1.92	2.659(3)	144
C6H6O3ⁱ	0.93	2.57	3.442(4)	157
C17H17CO2ⁱⁱ	0.96	2.46	3.176(4)	132

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and the University Sultan Moulay Slimane, Beni-Mellal, for financial support.

supplementary crystallographic information

S1. Comment

Urea derivatives are very interesting reagents due to their useful properties and important medical and biological applications, such as insecticidal, fungicidal, herbicidal, anti-infectives and plant-growth regulating activities (Abad et al., 2004; Chen et al., 2005, Batra et al., 2006), especially cytokinin activity (Wang et al., 2001; Ricci et al., 2005). Symmetrical disubstituted ureas generally form a polar hydrogen-bond chain, with anti NH donors and carbonyl O-atom acceptors in a bifurcated motif. As part of our studies in this area, the title compound C₁₇H₁₆N₂O₅ was synthesized and its crystal structure is reported in the present work.

The molecular structure of the title compound, a symmetrical urea derivative, is displayed in Fig. 1. This molecule is build up from two methyl benzoate linked through N–C(=O)–N fragment but not symmetric. The dihedral angle between the two phenyl rings (C3 to C8) and (C10 to C15) is of 42.1 (1)°.

In the crystal, the molecular conformation is stabilized by two intramolecular N—H···O hydrogen bonds and each molecule is linked to its symmetric by two intermolecular C—H···O hydrogen bonds to form centrosymmetric dimers as shown in Fig.2.

S2. Experimental

A solution of 2-(methoxycarbonyl)benzoic acid (100 mg, 0.56 mmol), DPPA (0.194 ml, 0.90 mmol) and Et₃N (0.127 ml, 0.90 mmol) in toluene (3 ml) was refluxed for 4 h. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by column chromatography using EtOAc-Hexane (1:9 v/v) as eluent to give yellow blocks with yield = 40% and m.p. = 411 K.