Methyl (2Z)-3-[(4-nitro­phen­yl)carbamo­yl]prop-2-enoate

Khurram Shahzad Munawar; Saqib Ali; M Nawaz Tahir

doi:10.1107/S1600536810050956

. 2010 Dec 11;67(Pt 1):o77. doi: 10.1107/S1600536810050956

Methyl (2Z)-3-[(4-nitrophenyl)carbamoyl]prop-2-enoate

Khurram Shahzad Munawar ^a, Saqib Ali ^a, M Nawaz Tahir ^b,^*

PMCID: PMC3050372 PMID: 21522788

Abstract

In the title compound, C₁₁H₁₀N₂O₅, the amide group is nearly coplanar and the ester group approximately perpendicular to the vinyl C—HC=CH—C group [dihedral angles of 5.0 (2) and 88.89 (5)°, respectively]. This results in a short intramolecular O =C⋯O=C contact of 2.7201 (17) Å between the amide O atom and the ester carbonyl C atom. The prop-2-enamide fragment and the nitro group make dihedral angles of 20.42 (6) and 13.54 (17)°, respectively, with the benzene ring. An intramolecular C—H⋯O interaction between the benzene ring and the amide group generates an S(6) ring motif. Intermolecular C—H⋯O and N—H⋯O hydrogen bonds complete R ₂ ²(11) ring motifs and join molecules into [100] chains.

Related literature

For crystal structures of N-substituted maleamic acids, see: Lo & Ng (2009 ▶); Wardell et al. (2005 ▶). For the synthesis of (4-[(4-nitrophenyl)amino]-4-oxobut-2-enoic acid, see: Shahid et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₁₀N₂O₅
M _r = 250.21
Triclinic,
a = 6.8382 (2) Å
b = 7.7497 (2) Å
c = 11.8277 (5) Å
α = 97.805 (2)°
β = 92.119 (2)°
γ = 114.425 (1)°
V = 562.39 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.35 × 0.26 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.897, T _max = 0.922
8150 measured reflections
2021 independent reflections
1754 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.097
S = 1.08
2021 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050956/gk2328sup1.cif

e-67-00o77-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050956/gk2328Isup2.hkl

e-67-00o77-Isup2.hkl^{(97.3KB, hkl)}

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—H1⋯O2ⁱ	0.86	2.11	2.9467 (17)	164
C7—H7⋯O3	0.93	2.33	2.8983 (17)	119
C11—H12⋯O3ⁱ	0.93	2.45	3.3020 (19)	152

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Symmetry code: (i) Inline graphic .

Acknowledgments

SA and KS Munawar are grateful to the Pakistan Science Foundation for financial support, project No. PSF/R and D/C–QU/CHEM (270).

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) has been crystallized in an attempt to synthesize the vanadium complex of 3-(4-nitrophenylaminocarbonyl)prop-2-enoic acid.

The crystal structure of N-phenylmaleamic acid (II) (Lo & Ng, 2009) and (E)-3-(4-nitrophenylaminocarbonyl)prop-2-enoic acid (III) (Wardell et al., 2005) have been published which are related to (I).

In (I), the methyl formate and prop-2-enamide moieties A (C1/O1/C2/O2) and B (C3/C4/C5/N1/O3) are planar with r. m. s. deviations of 0.012 and 0.019 Å, respectively. The benzene ring C (C6—C11) is planar with r. m. s. deviation of 0.008 Å. The nitro group D (N2/O4/O5) is of course planar. The dihedral angle between A/B, A/C, A/D, B/C, B/D and C/D is 88.78 (4), 86.03 (5), 80.82 (14), 20.42 (6), 12.62 (20) and 13.54 (17)°, respectively. In (I) the value of C═C is 1.318 (2) Å. There exists an intramolecular hydrogen bonding of C—H···O type (Table 1, Fig. 1) completing an S(6) ring motif (Bernstein et al., 1995). There exist intermolecular hydrogen bondings of C—H···O and N—H···O types (Table 1, Fig. 2). Due to these H-bondings R₂²(11) ring motifs are formed and the molecules are finally stabilized in the form of one dimensional polymeric chains extending along the crystallographic a axis (Fig. 2).

Experimental

3-(4-Nitrophenylaminocarbonyl)prop-2-enoic acid was prepared according to the procedure reported by Shahid et al. (2006). 3-(4-Nitrophenylaminocarbonyl)prop-2-enoic acid (3 mmol) and VCl₃ (1 mmol) were refluxed in methanol for 4 h resulting in greenish solution. Light green prisms of the title compound were formed after two days.