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ISSN: 2056-9890

Ethyl (2E)-2-cyano-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 August 2011; accepted 7 August 2011; online 11 August 2011)

The 15 non-H atoms of the title compound, C11H12N2O2, are approximately coplanar, the r.m.s. deviation being 0.145 Å. The major deviation from coplanarity is seen in a twist between the ethene (E configuration) and pyrrole rings [C—C—N—C torsion angle = −8.26 (18)°]. The carbonyl O and cyano N atoms are syn to each other. In the crystal, supra­molecular linear tapes linked by C—H⋯O and C—H⋯N inter­actions are further connected by C—H⋯π(pyrrole) inter­actions.

Related literature

For background to the biological activity of 2(1H)pyridone compounds, see: Aly et al. (1991[Aly, A. S., El-Ezabawy, S. R. & Abdel-Fattah, A. M. (1991). Egypt. J. Pharm. Sci. 32, 827-834.]); Al-Saadi et al. (2005[Al-Saadi, S. M., Rostom, S. A. F. & Faid Allah, H. M. (2005). Alex. J. Pharm. Sci, 19, 15-21.]); Rostom et al. (2011[Rostom, S. A. F., Faidallah, S. M. & Al Saadi, M. S. (2011). Med. Chem. Res. doi:10.1007/s00044-010-9469-0.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12N2O2

  • Mr = 204.23

  • Triclinic, [P \overline 1]

  • a = 7.6145 (3) Å

  • b = 8.4964 (6) Å

  • c = 9.7023 (6) Å

  • α = 64.898 (7)°

  • β = 89.859 (4)°

  • γ = 71.517 (5)°

  • V = 532.69 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.30 × 0.25 × 0.10 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.955, Tmax = 1.000

  • 4049 measured reflections

  • 2336 independent reflections

  • 1912 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.106

  • S = 1.04

  • 2336 reflections

  • 138 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N2,C7—C10 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11a⋯O2i 0.98 2.31 3.241 (2) 158
C9—H9⋯N1ii 0.95 2.62 3.557 (2) 171
C11—H11b⋯Cg1iii 0.98 2.69 3.5332 (17) 144
Symmetry codes: (i) x-1, y+1, z; (ii) -x+1, -y+2, -z; (iii) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The title compound (I) was studied in connection with the known biological activity of 2(1H)pyridone compounds (Aly et al., 1991; Al-Saadi et al., 2005; Rostom et al., 2011), and was prepared from the condensation of the N-methylpyrrole-2-carboxaldehyde with ethyl cyanoacetate during an attempt to prepare a 2(1H)pyridone derivative.

The molecular structure of (I), Fig. 1, is, to a first approximation, planar with the r.m.s. deviation for all 15 non-H atoms being 0.145 Å. The major deviations from the least-squares plane are 0.214 (2) and -0.337 (2) Å for the C9 and C11 atoms, respectively, reflecting a small twist between the ethene and pyrrole rings [the C11—N2—C7—C6 torsion angle = -8.26 (18) °]. The conformation about the ethene [C4C7 = 1.3594 (18) Å] bond is E. The carbonyl-O and cyano-N atoms are syn to each other.

In the crystal packing, molecules are linked into chains via C—H···O interactions involving a N-bound methyl-H and carbonyl-O, Table 1. Chains are linked into a linear tape via C—H···N interactions involving a pyrrole-H and cyano-N, Fig. 2. The tapes are consolidated into the three-dimensional architecture by C—H···π interactions, Fig. 3, involving another N-bound methyl-H as the donor to the pyrrole ring.

Related literature top

For background to the biological activity of 2(1H)pyridone compounds, see: Aly et al. (1991); Al-Saadi et al. (2005); Rostom et al. (2011).

Experimental top

A mixture of the N-methylpyrrole-2-carboxaldehyde (1.0 g,1 0 mmol), 2-methylcyclohexanone (1.12 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool, the formed precipitate was filtered, washed with water, dried and recrystallized from ethanol to form yellow blocks. M.pt. 420–421 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.99 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Supramolecular tape in (I) mediated by C—H···O and C—H···N interactions shown as orange and blue dashed lines, respectively.
[Figure 3] Fig. 3. A view in projection down the b axis of the unit-cell contents of (I). The C—H···O, C—H···N and C—H···π interactions shown as orange, blue and purple dashed lines, respectively.
Ethyl (2E)-2-cyano-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate top
Crystal data top
C11H12N2O2Z = 2
Mr = 204.23F(000) = 216
Triclinic, P1Dx = 1.273 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6145 (3) ÅCell parameters from 2042 reflections
b = 8.4964 (6) Åθ = 2.3–29.2°
c = 9.7023 (6) ŵ = 0.09 mm1
α = 64.898 (7)°T = 100 K
β = 89.859 (4)°Block, yellow
γ = 71.517 (5)°0.30 × 0.25 × 0.10 mm
V = 532.69 (5) Å3
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
2336 independent reflections
Radiation source: SuperNova (Mo) X-ray Source1912 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.030
Detector resolution: 10.4041 pixels mm-1θmax = 27.5°, θmin = 2.4°
ω scansh = 89
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 811
Tmin = 0.955, Tmax = 1.000l = 1211
4049 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.043P)2 + 0.1378P]
where P = (Fo2 + 2Fc2)/3
2336 reflections(Δ/σ)max < 0.001
138 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C11H12N2O2γ = 71.517 (5)°
Mr = 204.23V = 532.69 (5) Å3
Triclinic, P1Z = 2
a = 7.6145 (3) ÅMo Kα radiation
b = 8.4964 (6) ŵ = 0.09 mm1
c = 9.7023 (6) ÅT = 100 K
α = 64.898 (7)°0.30 × 0.25 × 0.10 mm
β = 89.859 (4)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
2336 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
1912 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 1.000Rint = 0.030
4049 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.04Δρmax = 0.26 e Å3
2336 reflectionsΔρmin = 0.21 e Å3
138 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.76560 (13)0.39008 (13)0.75762 (10)0.0210 (2)
O20.94151 (13)0.24631 (13)0.62962 (11)0.0240 (2)
N20.31730 (15)0.98384 (16)0.40412 (13)0.0195 (3)
C10.7806 (2)0.2663 (2)1.02981 (18)0.0367 (4)
H1A0.83940.15791.12870.055*
H1B0.64520.29281.01650.055*
H1C0.80490.37371.02800.055*
C20.8606 (2)0.22752 (19)0.90199 (16)0.0239 (3)
H2A0.99700.20360.91280.029*
H2B0.84020.11700.90450.029*
C30.82056 (17)0.37907 (18)0.63059 (15)0.0178 (3)
C40.71681 (17)0.54814 (18)0.48907 (15)0.0177 (3)
C50.77316 (18)0.54540 (18)0.34926 (16)0.0198 (3)
C60.57429 (17)0.68970 (18)0.49404 (15)0.0176 (3)
H60.54550.67060.59400.021*
C70.46245 (17)0.86137 (18)0.37221 (15)0.0185 (3)
C80.47051 (19)0.95100 (19)0.21554 (16)0.0225 (3)
H80.55590.90150.16030.027*
C90.3314 (2)1.1258 (2)0.15416 (17)0.0268 (3)
H90.30511.21710.04990.032*
C100.23870 (19)1.14206 (19)0.27246 (16)0.0241 (3)
H100.13641.24710.26310.029*
C110.25065 (19)0.9441 (2)0.55193 (16)0.0230 (3)
H11A0.15561.05680.54620.034*
H11B0.35590.90130.63230.034*
H11C0.19560.84730.57670.034*
N10.81855 (17)0.53952 (17)0.23809 (14)0.0273 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0231 (5)0.0179 (5)0.0169 (5)0.0016 (4)0.0022 (4)0.0073 (4)
O20.0218 (5)0.0215 (5)0.0278 (6)0.0014 (4)0.0028 (4)0.0145 (4)
N20.0176 (5)0.0198 (6)0.0224 (6)0.0041 (5)0.0011 (4)0.0122 (5)
C10.0394 (9)0.0389 (10)0.0209 (8)0.0062 (8)0.0046 (7)0.0089 (7)
C20.0269 (7)0.0183 (7)0.0187 (7)0.0043 (6)0.0005 (6)0.0038 (6)
C30.0163 (6)0.0193 (7)0.0206 (7)0.0061 (5)0.0036 (5)0.0116 (6)
C40.0167 (6)0.0202 (7)0.0194 (7)0.0076 (5)0.0035 (5)0.0108 (6)
C50.0183 (6)0.0179 (7)0.0225 (7)0.0044 (5)0.0019 (5)0.0098 (6)
C60.0169 (6)0.0211 (7)0.0190 (7)0.0084 (5)0.0037 (5)0.0115 (5)
C70.0174 (6)0.0190 (7)0.0208 (7)0.0054 (5)0.0019 (5)0.0111 (6)
C80.0254 (7)0.0231 (7)0.0204 (7)0.0069 (6)0.0011 (5)0.0120 (6)
C90.0305 (8)0.0234 (8)0.0213 (7)0.0055 (6)0.0048 (6)0.0082 (6)
C100.0211 (7)0.0194 (7)0.0282 (8)0.0012 (6)0.0045 (6)0.0115 (6)
C110.0199 (7)0.0251 (8)0.0283 (8)0.0059 (6)0.0061 (6)0.0172 (6)
N10.0325 (7)0.0267 (7)0.0234 (7)0.0074 (6)0.0076 (5)0.0139 (5)
Geometric parameters (Å, º) top
O1—C31.3316 (16)C4—C51.4290 (19)
O1—C21.4570 (16)C5—N11.1482 (17)
O2—C31.2128 (15)C6—C71.4158 (18)
N2—C101.3542 (18)C6—H60.9500
N2—C71.3938 (17)C7—C81.3933 (19)
N2—C111.4568 (18)C8—C91.392 (2)
C1—C21.494 (2)C8—H80.9500
C1—H1A0.9800C9—C101.380 (2)
C1—H1B0.9800C9—H90.9500
C1—H1C0.9800C10—H100.9500
C2—H2A0.9900C11—H11A0.9800
C2—H2B0.9900C11—H11B0.9800
C3—C41.4783 (18)C11—H11C0.9800
C4—C61.3594 (18)
C3—O1—C2115.44 (10)N1—C5—C4178.60 (15)
C10—N2—C7108.92 (11)C4—C6—C7129.52 (13)
C10—N2—C11125.09 (11)C4—C6—H6115.2
C7—N2—C11125.83 (11)C7—C6—H6115.2
C2—C1—H1A109.5C8—C7—N2106.74 (11)
C2—C1—H1B109.5C8—C7—C6133.53 (12)
H1A—C1—H1B109.5N2—C7—C6119.56 (12)
C2—C1—H1C109.5C9—C8—C7107.97 (13)
H1A—C1—H1C109.5C9—C8—H8126.0
H1B—C1—H1C109.5C7—C8—H8126.0
O1—C2—C1107.45 (11)C10—C9—C8107.48 (13)
O1—C2—H2A110.2C10—C9—H9126.3
C1—C2—H2A110.2C8—C9—H9126.3
O1—C2—H2B110.2N2—C10—C9108.89 (12)
C1—C2—H2B110.2N2—C10—H10125.6
H2A—C2—H2B108.5C9—C10—H10125.6
O2—C3—O1124.42 (12)N2—C11—H11A109.5
O2—C3—C4123.32 (12)N2—C11—H11B109.5
O1—C3—C4112.26 (11)H11A—C11—H11B109.5
C6—C4—C5123.65 (12)N2—C11—H11C109.5
C6—C4—C3121.69 (12)H11A—C11—H11C109.5
C5—C4—C3114.60 (11)H11B—C11—H11C109.5
C3—O1—C2—C1179.92 (11)C10—N2—C7—C6176.08 (11)
C2—O1—C3—O20.45 (18)C11—N2—C7—C68.26 (18)
C2—O1—C3—C4179.47 (10)C4—C6—C7—C88.2 (2)
O2—C3—C4—C6175.93 (12)C4—C6—C7—N2177.34 (12)
O1—C3—C4—C63.99 (17)N2—C7—C8—C90.03 (15)
O2—C3—C4—C51.38 (18)C6—C7—C8—C9174.98 (14)
O1—C3—C4—C5178.70 (10)C7—C8—C9—C100.29 (16)
C5—C4—C6—C74.1 (2)C7—N2—C10—C90.43 (15)
C3—C4—C6—C7178.85 (12)C11—N2—C10—C9176.13 (12)
C10—N2—C7—C80.24 (14)C8—C9—C10—N20.44 (16)
C11—N2—C7—C8175.90 (11)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N2,C7—C10 ring.
D—H···AD—HH···AD···AD—H···A
C11—H11a···O2i0.982.313.241 (2)158
C9—H9···N1ii0.952.623.557 (2)171
C11—H11b···Cg1iii0.982.693.5332 (17)144
Symmetry codes: (i) x1, y+1, z; (ii) x+1, y+2, z; (iii) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC11H12N2O2
Mr204.23
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.6145 (3), 8.4964 (6), 9.7023 (6)
α, β, γ (°)64.898 (7), 89.859 (4), 71.517 (5)
V3)532.69 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.25 × 0.10
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.955, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
4049, 2336, 1912
Rint0.030
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.106, 1.04
No. of reflections2336
No. of parameters138
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.21

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N2,C7—C10 ring.
D—H···AD—HH···AD···AD—H···A
C11—H11a···O2i0.982.313.241 (2)158
C9—H9···N1ii0.952.623.557 (2)171
C11—H11b···Cg1iii0.982.693.5332 (17)144
Symmetry codes: (i) x1, y+1, z; (ii) x+1, y+2, z; (iii) x+1, y+2, z+1.
 

Footnotes

Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

References

First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
First citationAl-Saadi, S. M., Rostom, S. A. F. & Faid Allah, H. M. (2005). Alex. J. Pharm. Sci, 19, 15–21.  CAS Google Scholar
First citationAly, A. S., El-Ezabawy, S. R. & Abdel-Fattah, A. M. (1991). Egypt. J. Pharm. Sci. 32, 827–834.  CAS Google Scholar
First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationRostom, S. A. F., Faidallah, S. M. & Al Saadi, M. S. (2011). Med. Chem. Res. doi:10.1007/s00044-010-9469-0.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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