Ethyl 5-methyl-1H-pyrrole-2-carboxyl-ate.

Abstract

In the title mol-ecule, C(8)H(11)NO(2), the r.m.s. deviation of non-H atoms from their best plane is 0.031 Å. Mol-ecules are connected via a pair of N-H⋯O hydrogen bonds into a centrosymmetric dimer.

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Ethyl 5-methyl-1H-pyrrole-2-carboxylate
Zhao-Po Zhang,aYuan Wanga* and Xiao-Xia Lib
aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo
454000, People’s Republic of China, andbInstitute 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
Key indicators: single-crystal X-ray study; T = 296 K; mean ?(C–C) = 0.003 A ˚;
R factor = 0.045; wR factor = 0.143; data-to-parameter ratio = 19.5.
In the title molecule, C8H11NO2, the r.m.s. deviation of non-H
atoms from their best plane is 0.031 A˚. 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). For the synthesis of the
title compound, see: Motekaitis et al. (1970).
Experimental
Crystal data
C8H11NO2
Mr= 153.18
Monoclinic, P21=c
a = 7.0759 (3) A˚
b = 18.0705 (9) A˚
c = 6.6606 (3) A˚
? = 101.349 (3)?
V = 835.01 (7) A˚3
Z = 4
Mo K? radiation
? = 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)
Tmin= 0.984, Tmax= 0.989
7496 measured reflections
1991 independent reflections
1157 reflections with I > 2?(I)
Rint= 0.029
Refinement
R[F2> 2?(F2)] = 0.045
wR(F2) = 0.143
S = 1.02
1991 reflections
102 parameters
H-atom parameters constrained
??max= 0.16 e A˚?3
??min= ?0.16 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
N1—H1???O1i
Symmetry code: (i) ?x þ 1;?y þ 1;?z þ 2.
D—HH???AD???AD—H???A
0.861.99 2.8363 (19) 167
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT
(Bruker, 2007); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure:SHELXL97 (Sheldrick,
SHELXTL (Sheldrick, 2008); software used to prepare material for
publication: SHELXTL.
2008);moleculargraphics:
The authors are grateful to the National Natural Science
Foundation of China for financial support (grant No.
21001040).
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: GK2381).
References
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,
Wisconsin, USA.
Motekaitis, R. J., Heinert, H. D. & Martell, A. E. (1970). J. Org. Chem. 35,
2504–2511.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Zhang, Y.-H., Yin, Z., Li, X.-F., He, J. & Cheng, J.-P. (2003). Acta Cryst. E59,
o1881–o1882.
organic compounds
Acta Cryst. (2011). E67, o1585doi:10.1107/S1600536811021180Zhang et al.
o1585
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials

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supplementary materials
sup-1
Acta Cryst. (2011). E67, o1585 [ doi:10.1107/S1600536811021180 ]
Ethyl 5-methyl-1H-pyrrole-2-carboxylate
Z.-P. Zhang, Y. Wang and X.-X. Li
Comment
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).
Experimental
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
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.
Figures
Fig. 1. The title compound with the displacement ellipsoids shown at the 50% probability
level.
Fig. 2. The centrosymmetric dimer via N-H···O hydrogen bonds of the title compound (hydro-
gen bonds shown as dashed lines, symmetry code:: 1 - x, 1 - y, 2 - z).
Ethyl 5-methyl-1H-pyrrole-2-carboxylate
Crystal data
C8H11NO2
F(000) = 328
Dx = 1.218 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Mr = 153.18
Monoclinic, P21/c

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supplementary materials
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Hall symbol: -P 2ybc
a = 7.0759 (3) Å
Cell parameters from 2070 reflections
θ = 2.3–24.2°
µ = 0.09 mm−1
T = 296 K
Plate, colorless
b = 18.0705 (9) Å
c = 6.6606 (3) Å
β = 101.349 (3)°
V = 835.01 (7) Å3
Z = 4
0.20 × 0.15 × 0.13 mm
Data collection
Bruker APEXII CCD
diffractometer
Radiation source: fine-focus sealed tube
graphite
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
Tmin = 0.984, Tmax = 0.989
7496 measured reflections
1991 independent reflections
1157 reflections with I > 2σ(I)
Rint = 0.029
θmax = 27.9°, θmin = 2.3°
h = −9→9
k = −23→23
l = −8→8
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.045
wR(F2) = 0.143
H-atom parameters constrained
S = 1.02
w = 1/[σ2(Fo2) + (0.0683P)2 + 0.0738P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.16 e Å−3
Δρmin = −0.16 e Å−3
1991 reflections
102 parameters
0 restraints
Special details
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 mat-
rix. 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, convention-
al 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.

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
0.12507 (16)
0.52408 (19)
0.5637
0.2631 (2)
0.2888 (2)
0.3729 (2)
0.6023 (2)
−0.1423 (3)
−0.0794
−0.2268
−0.2159
0.3561 (2)
0.2658
0.0051 (3)
0.0825
−0.0569
0.7719 (3)
0.8862
0.7543
0.7847
0.4987 (3)
0.5200
y
0.64959 (6)
0.57393 (7)
0.5360
0.60036 (9)
0.54602 (8)
0.61798 (9)
0.59835 (10)
0.69326 (11)
0.7400
0.6837
0.6946
0.67196 (10)
0.7100
0.63353 (10)
0.6324
0.5858
0.56133 (11)
0.5893
0.5585
0.5123
0.65956 (10)
0.6879
z
0.92921 (18)
0.7402 (2)
0.8146
0.9187 (3)
1.0272 (2)
0.7644 (2)
0.5831 (3)
1.0591 (3)
1.0916
1.1527
0.9217
0.6178 (3)
0.5976
1.0768 (3)
1.2142
1.0480
0.5261 (3)
0.5791
0.3796
0.5827
0.5044 (3)
0.3944
Uiso*/Ueq
0.0629 (4)
0.0581 (4)
0.087*
0.0585 (4)
0.0861 (5)
0.0548 (4)
0.0600 (5)
0.0768 (6)
0.115*
0.115*
0.115*
0.0651 (5)
0.078*
0.0691 (5)
0.083*
0.083*
0.0780 (6)
0.117*
0.117*
0.117*
0.0712 (5)
0.085*
O2
N1
H1
C6
O1
C5
C2
C8
H8A
H8B
H8C
C4
H4
C7
H7A
H7B
C1
H1A
H1B
H1C
C3
H3
Atomic displacement parameters (Å2)
U11
0.0581 (7)
0.0533 (8)
0.0519 (9)
0.0847 (10)
0.0486 (9)
0.0539 (9)
0.0689 (12)
0.0587 (10)
0.0635 (11)
0.0664 (12)
0.0683 (11)
U22
0.0624 (7)
0.0560 (8)
0.0563 (9)
0.0820 (9)
0.0532 (9)
0.0652 (10)
0.0819 (13)
0.0616 (10)
0.0788 (12)
0.0894 (14)
0.0781 (12)
U33
0.0748 (8)
0.0691 (9)
0.0698 (11)
0.1032 (11)
0.0649 (11)
0.0644 (11)
0.0884 (15)
0.0766 (12)
0.0716 (12)
0.0867 (14)
0.0715 (12)
U12
0.0073 (5)
0.0001 (6)
0.0019 (8)
0.0273 (8)
−0.0015 (7)
−0.0091 (8)
0.0074 (10)
0.0036 (8)
0.0050 (9)
−0.0022 (10)
−0.0023 (10)
U13
0.0294 (6)
0.0221 (7)
0.0182 (8)
0.0467 (8)
0.0165 (8)
0.0202 (8)
0.0373 (11)
0.0172 (9)
0.0293 (9)
0.0360 (10)
0.0246 (10)
U23
0.0035 (6)
0.0000 (6)
−0.0026 (9)
0.0332 (8)
−0.0035 (8)
−0.0063 (8)
−0.0054 (10)
0.0060 (9)
0.0048 (9)
−0.0094 (11)
0.0107 (10)
O2
N1
C6
O1
C5
C2
C8
C4
C7
C1
C3
Geometric parameters (Å, °)
C2—C1
C2—C3
C4—C3
C5—C4
N1—C2
1.487 (2)
1.373 (3)
1.392 (2)
1.369 (2)
1.351 (2)
C1—H1A
C1—H1B
C1—H1C
C3—H3
C4—H4
0.9600
0.9600
0.9600
0.9300
0.9300