organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Ethyl 5-methyl-1H-pyrrole-2-carboxyl­ate

aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China, and bInstitute of Functional Materials, Jiangxi University of Finance and Economics, Nanchang 330013, People's Republic of China
*Correspondence e-mail: wangyuan08@hpu.edu.cn

(Received 1 June 2011; accepted 1 June 2011; online 4 June 2011)

In the title mol­ecule, C8H11NO2, the r.m.s. deviation of non-H atoms from their best plane is 0.031 Å. Mol­ecules are connected via a pair of N—H⋯O hydrogen bonds into a centrosymmetric dimer.

Related literature

For the crystal structure of the 5-cyano analogue of the title compound, see: Zhang et al. (2003[Zhang, Y.-H., Yin, Z., Li, X.-F., He, J. & Cheng, J.-P. (2003). Acta Cryst. E59, o1881-o1882.]). For the synthesis of the title compound, see: Motekaitis et al. (1970[Motekaitis, R. J., Heinert, H. D. & Martell, A. E. (1970). J. Org. Chem. 35, 2504-2511.]).

[Scheme 1]

Experimental

Crystal data
  • C8H11NO2

  • Mr = 153.18

  • Monoclinic, P 21 /c

  • a = 7.0759 (3) Å

  • b = 18.0705 (9) Å

  • c = 6.6606 (3) Å

  • β = 101.349 (3)°

  • V = 835.01 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.20 × 0.15 × 0.13 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.989

  • 7496 measured reflections

  • 1991 independent reflections

  • 1157 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.143

  • S = 1.02

  • 1991 reflections

  • 102 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.86 1.99 2.8363 (19) 167
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

As part of our studies on hydrazone ligands bearing pyrrole unit the title compound was synthesized and characterized by X-ray diffraction.

The non-hydrogen atoms of the title molecule (Fig. 1) are situated in a fair plane (r.m.s. deviation of the non-hydrogen atoms being 0.0306 Å). In the crystal, the molecules are linked into a centrosymmetric dimer by two intermolecular N—H···O hydrogen bonds, forming a R22(10) ring motif (Table 1, Fig. 2).

Related literature top

For the crystal structure of the 5-cyano analogue of the title compound, see: Zhang et al. (2003). For the synthesis of the title compound, see: Motekaitis et al. (1970).

Experimental top

The title compound was synthesized according to the literature procedure (Motekaitis et al., 1970). The crude orange solid was washed well with ice water and dried in air. Colorless plates of the title compound were obtained by slow evaporation of petroleum ether/ethyl acetate (100:1) solution.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and were thereafter treated as riding, with Uiso(H) values of 1.5Ueq(C) for methyl groups and 1.2Ueq(C,N) for others.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The title compound with the displacement ellipsoids shown at the 50% probability level.
[Figure 2] Fig. 2. The centrosymmetric dimer via N-H···O hydrogen bonds of the title compound (hydrogen bonds shown as dashed lines, symmetry code:: 1 - x, 1 - y, 2 - z).
Ethyl 5-methyl-1H-pyrrole-2-carboxylate top
Crystal data top
C8H11NO2F(000) = 328
Mr = 153.18Dx = 1.218 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2070 reflections
a = 7.0759 (3) Åθ = 2.3–24.2°
b = 18.0705 (9) ŵ = 0.09 mm1
c = 6.6606 (3) ÅT = 296 K
β = 101.349 (3)°Plate, colorless
V = 835.01 (7) Å30.20 × 0.15 × 0.13 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
1991 independent reflections
Radiation source: fine-focus sealed tube1157 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 27.9°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 99
Tmin = 0.984, Tmax = 0.989k = 2323
7496 measured reflectionsl = 88
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0683P)2 + 0.0738P]
where P = (Fo2 + 2Fc2)/3
1991 reflections(Δ/σ)max < 0.001
102 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C8H11NO2V = 835.01 (7) Å3
Mr = 153.18Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.0759 (3) ŵ = 0.09 mm1
b = 18.0705 (9) ÅT = 296 K
c = 6.6606 (3) Å0.20 × 0.15 × 0.13 mm
β = 101.349 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
1991 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
1157 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.989Rint = 0.029
7496 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
1991 reflectionsΔρmin = 0.16 e Å3
102 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
O20.12507 (16)0.64959 (6)0.92921 (18)0.0629 (4)
N10.52408 (19)0.57393 (7)0.7402 (2)0.0581 (4)
H10.56370.53600.81460.087*
C60.2631 (2)0.60036 (9)0.9187 (3)0.0585 (4)
O10.2888 (2)0.54602 (8)1.0272 (2)0.0861 (5)
C50.3729 (2)0.61798 (9)0.7644 (2)0.0548 (4)
C20.6023 (2)0.59835 (10)0.5831 (3)0.0600 (5)
C80.1423 (3)0.69326 (11)1.0591 (3)0.0768 (6)
H8A0.07940.74001.09160.115*
H8B0.22680.68371.15270.115*
H8C0.21590.69460.92170.115*
C40.3561 (2)0.67196 (10)0.6178 (3)0.0651 (5)
H40.26580.71000.59760.078*
C70.0051 (3)0.63353 (10)1.0768 (3)0.0691 (5)
H7A0.08250.63241.21420.083*
H7B0.05690.58581.04800.083*
C10.7719 (3)0.56133 (11)0.5261 (3)0.0780 (6)
H1A0.88620.58930.57910.117*
H1B0.75430.55850.37960.117*
H1C0.78470.51230.58270.117*
C30.4987 (3)0.65956 (10)0.5044 (3)0.0712 (5)
H30.52000.68790.39440.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0581 (7)0.0624 (7)0.0748 (8)0.0073 (5)0.0294 (6)0.0035 (6)
N10.0533 (8)0.0560 (8)0.0691 (9)0.0001 (6)0.0221 (7)0.0000 (6)
C60.0519 (9)0.0563 (9)0.0698 (11)0.0019 (8)0.0182 (8)0.0026 (9)
O10.0847 (10)0.0820 (9)0.1032 (11)0.0273 (8)0.0467 (8)0.0332 (8)
C50.0486 (9)0.0532 (9)0.0649 (11)0.0015 (7)0.0165 (8)0.0035 (8)
C20.0539 (9)0.0652 (10)0.0644 (11)0.0091 (8)0.0202 (8)0.0063 (8)
C80.0689 (12)0.0819 (13)0.0884 (15)0.0074 (10)0.0373 (11)0.0054 (10)
C40.0587 (10)0.0616 (10)0.0766 (12)0.0036 (8)0.0172 (9)0.0060 (9)
C70.0635 (11)0.0788 (12)0.0716 (12)0.0050 (9)0.0293 (9)0.0048 (9)
C10.0664 (12)0.0894 (14)0.0867 (14)0.0022 (10)0.0360 (10)0.0094 (11)
C30.0683 (11)0.0781 (12)0.0715 (12)0.0023 (10)0.0246 (10)0.0107 (10)
Geometric parameters (Å, º) top
C2—C11.487 (2)C1—H1A0.9600
C2—C31.373 (3)C1—H1B0.9600
C4—C31.392 (2)C1—H1C0.9600
C5—C41.369 (2)C3—H30.9300
N1—C21.351 (2)C4—H40.9300
N1—C51.368 (2)C7—H7A0.9700
C6—C51.440 (2)C7—H7B0.9700
C6—O11.212 (2)C8—H8A0.9600
O2—C61.3333 (19)C8—H8B0.9600
O2—C71.4490 (19)C8—H8C0.9600
C8—C71.490 (2)N1—H10.8600
C6—O2—C7115.81 (13)C5—C4—C3107.57 (16)
C2—N1—C5110.53 (14)C5—C4—H4126.2
C2—N1—H1124.7C3—C4—H4126.2
C5—N1—H1124.7O2—C7—C8107.22 (15)
O1—C6—O2122.31 (15)O2—C7—H7A110.3
O1—C6—C5124.50 (15)C8—C7—H7A110.3
O2—C6—C5113.19 (15)O2—C7—H7B110.3
C4—C5—N1106.89 (14)C8—C7—H7B110.3
C4—C5—C6133.09 (16)H7A—C7—H7B108.5
N1—C5—C6119.97 (15)C2—C1—H1A109.5
N1—C2—C3106.81 (15)C2—C1—H1B109.5
N1—C2—C1121.69 (16)H1A—C1—H1B109.5
C3—C2—C1131.48 (17)C2—C1—H1C109.5
C7—C8—H8A109.5H1A—C1—H1C109.5
C7—C8—H8B109.5H1B—C1—H1C109.5
H8A—C8—H8B109.5C2—C3—C4108.20 (16)
C7—C8—H8C109.5C2—C3—H3125.9
H8A—C8—H8C109.5C4—C3—H3125.9
H8B—C8—H8C109.5
C7—O2—C6—O10.9 (2)C5—N1—C2—C30.1 (2)
C7—O2—C6—C5177.93 (14)C5—N1—C2—C1178.73 (15)
C2—N1—C5—C40.12 (19)N1—C5—C4—C30.26 (19)
C2—N1—C5—C6177.58 (14)C6—C5—C4—C3177.02 (18)
O1—C6—C5—C4173.57 (18)C6—O2—C7—C8178.10 (14)
O2—C6—C5—C45.3 (3)N1—C2—C3—C40.2 (2)
O1—C6—C5—N13.4 (3)C1—C2—C3—C4178.40 (18)
O2—C6—C5—N1177.75 (13)C5—C4—C3—C20.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.861.992.8363 (19)167
Symmetry code: (i) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC8H11NO2
Mr153.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)7.0759 (3), 18.0705 (9), 6.6606 (3)
β (°) 101.349 (3)
V3)835.01 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.15 × 0.13
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.984, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
7496, 1991, 1157
Rint0.029
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.143, 1.02
No. of reflections1991
No. of parameters102
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.861.992.8363 (19)167.4
Symmetry code: (i) x+1, y+1, z+2.
 

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China for financial support (grant No. 21001040).

References

First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMotekaitis, R. J., Heinert, H. D. & Martell, A. E. (1970). J. Org. Chem. 35, 2504–2511.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhang, Y.-H., Yin, Z., Li, X.-F., He, J. & Cheng, J.-P. (2003). Acta Cryst. E59, o1881–o1882.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
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