Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C7H10N2O2, crystallizes as a nearly planar molecule. The carboxyethyl group is twisted by 4.43 (14)° relative to the plane that includes the imidazole group. The carbonyl unit of the carboxyethyl group is oriented anti to the N-methyl group of the imidazole.
Supporting information
CCDC reference: 605227
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.001 Å
- R factor = 0.030
- wR factor = 0.068
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
ethyl 1-methyimidazole-2-carboxylate
top
Crystal data top
C7H10N2O2 | F(000) = 328 |
Mr = 154.17 | Dx = 1.378 Mg m−3 |
Monoclinic, P21/c | Melting point = 43–44 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1040 (8) Å | Cell parameters from 5362 reflections |
b = 15.2244 (18) Å | θ = 2.7–28.0° |
c = 7.4511 (9) Å | µ = 0.10 mm−1 |
β = 112.797 (2)° | T = 100 K |
V = 742.92 (15) Å3 | Plate, colorless |
Z = 4 | 0.37 × 0.29 × 0.09 mm |
Data collection top
Bruker SMART APEX diffractometer | 1728 independent reflections |
Radiation source: fine-focus sealed tube | 1636 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
Detector resolution: no pixels mm-1 | θmax = 28.0°, θmin = 3.1° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | k = −19→19 |
Tmin = 0.960, Tmax = 0.988 | l = −9→9 |
6360 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.068 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0213P)2 + 0.3603P] where P = (Fo2 + 2Fc2)/3 |
1728 reflections | (Δ/σ)max = 0.001 |
140 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Special details top
Experimental. Data were collected with a Bruker SMART APEX CCD-based diffractometer
using /w-scans of width 0.3 °. and 30 s duration at a crystal-to-detector
distance of 4.908 cm. Intensity decay over the course of the data collection
was evaluated by recollecting the first 50 frames of data at the end of the
experiment. No significant decay was noted. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.25020 (11) | 0.57084 (4) | 0.39888 (9) | 0.01830 (16) | |
O2 | 0.23052 (11) | 0.46091 (5) | 0.59352 (10) | 0.02000 (17) | |
N1 | 0.24441 (12) | 0.45189 (5) | 0.11144 (11) | 0.01505 (17) | |
N2 | 0.19787 (12) | 0.34172 (5) | 0.28830 (12) | 0.01794 (18) | |
C1 | 0.22529 (13) | 0.42764 (6) | 0.28103 (13) | 0.01515 (19) | |
C2 | 0.20018 (15) | 0.30936 (7) | 0.11812 (14) | 0.0192 (2) | |
H2 | 0.1833 (19) | 0.2486 (9) | 0.0843 (18) | 0.022 (3)* | |
C3 | 0.22843 (14) | 0.37615 (7) | 0.00771 (14) | 0.0180 (2) | |
H3 | 0.2360 (19) | 0.3774 (8) | −0.1166 (19) | 0.022 (3)* | |
C4 | 0.27853 (15) | 0.53886 (6) | 0.04420 (14) | 0.0173 (2) | |
H4A | 0.1699 (19) | 0.5784 (8) | 0.0380 (17) | 0.020 (3)* | |
H4B | 0.4083 (19) | 0.5623 (8) | 0.1334 (18) | 0.019 (3)* | |
H4C | 0.2773 (19) | 0.5313 (8) | −0.0873 (19) | 0.023 (3)* | |
C5 | 0.23488 (13) | 0.48678 (6) | 0.44178 (13) | 0.01523 (19) | |
C6 | 0.25898 (15) | 0.63570 (6) | 0.54630 (14) | 0.0177 (2) | |
H6A | 0.3709 (18) | 0.6192 (7) | 0.6676 (17) | 0.015 (3)* | |
H6B | 0.1307 (18) | 0.6334 (8) | 0.5636 (17) | 0.017 (3)* | |
C7 | 0.29400 (17) | 0.72322 (7) | 0.46991 (15) | 0.0217 (2) | |
H7A | 0.304 (2) | 0.7695 (10) | 0.567 (2) | 0.036 (4)* | |
H7B | 0.179 (2) | 0.7379 (9) | 0.347 (2) | 0.028 (3)* | |
H7C | 0.421 (2) | 0.7219 (8) | 0.4487 (19) | 0.027 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0256 (4) | 0.0166 (3) | 0.0149 (3) | −0.0012 (3) | 0.0102 (3) | −0.0018 (3) |
O2 | 0.0254 (4) | 0.0216 (4) | 0.0146 (3) | −0.0001 (3) | 0.0095 (3) | 0.0010 (3) |
N1 | 0.0156 (4) | 0.0169 (4) | 0.0131 (4) | 0.0002 (3) | 0.0059 (3) | 0.0001 (3) |
N2 | 0.0186 (4) | 0.0174 (4) | 0.0181 (4) | −0.0004 (3) | 0.0074 (3) | 0.0000 (3) |
C1 | 0.0145 (4) | 0.0179 (4) | 0.0132 (4) | 0.0004 (3) | 0.0056 (3) | 0.0014 (3) |
C2 | 0.0193 (4) | 0.0182 (5) | 0.0200 (5) | −0.0008 (4) | 0.0077 (4) | −0.0032 (4) |
C3 | 0.0177 (4) | 0.0206 (5) | 0.0160 (4) | 0.0000 (4) | 0.0069 (4) | −0.0030 (4) |
C4 | 0.0200 (5) | 0.0175 (5) | 0.0157 (4) | −0.0002 (4) | 0.0084 (4) | 0.0020 (3) |
C5 | 0.0122 (4) | 0.0186 (5) | 0.0145 (4) | 0.0003 (3) | 0.0046 (3) | 0.0000 (3) |
C6 | 0.0214 (5) | 0.0179 (5) | 0.0152 (4) | 0.0003 (4) | 0.0089 (4) | −0.0027 (4) |
C7 | 0.0276 (5) | 0.0183 (5) | 0.0211 (5) | 0.0006 (4) | 0.0116 (4) | −0.0002 (4) |
Geometric parameters (Å, º) top
O1—C5 | 1.3338 (12) | C3—H3 | 0.948 (13) |
O1—C6 | 1.4604 (11) | C4—H4A | 0.966 (12) |
O2—C5 | 1.2089 (12) | C4—H4B | 0.972 (12) |
N1—C3 | 1.3682 (12) | C4—H4C | 0.983 (13) |
N1—C1 | 1.3728 (12) | C6—C7 | 1.5070 (14) |
N1—C4 | 1.4686 (12) | C6—H6A | 0.977 (12) |
N2—C1 | 1.3266 (12) | C6—H6B | 0.969 (12) |
N2—C2 | 1.3664 (13) | C7—H7A | 0.991 (15) |
C1—C5 | 1.4787 (13) | C7—H7B | 0.988 (14) |
C2—C3 | 1.3707 (14) | C7—H7C | 0.974 (13) |
C2—H2 | 0.954 (13) | | |
| | | |
C5—O1—C6 | 116.89 (7) | H4A—C4—H4C | 109.1 (10) |
C3—N1—C1 | 106.09 (8) | H4B—C4—H4C | 111.4 (10) |
C3—N1—C4 | 123.76 (8) | O2—C5—O1 | 124.81 (9) |
C1—N1—C4 | 130.15 (8) | O2—C5—C1 | 123.32 (9) |
C1—N2—C2 | 105.24 (8) | O1—C5—C1 | 111.87 (8) |
N2—C1—N1 | 111.79 (8) | O1—C6—C7 | 106.20 (8) |
N2—C1—C5 | 121.92 (8) | O1—C6—H6A | 107.7 (7) |
N1—C1—C5 | 126.29 (8) | C7—C6—H6A | 112.5 (7) |
N2—C2—C3 | 110.28 (9) | O1—C6—H6B | 107.9 (7) |
N2—C2—H2 | 123.3 (8) | C7—C6—H6B | 112.5 (7) |
C3—C2—H2 | 126.4 (8) | H6A—C6—H6B | 109.7 (10) |
N1—C3—C2 | 106.59 (8) | C6—C7—H7A | 109.2 (8) |
N1—C3—H3 | 120.7 (8) | C6—C7—H7B | 110.7 (8) |
C2—C3—H3 | 132.7 (8) | H7A—C7—H7B | 108.2 (11) |
N1—C4—H4A | 110.1 (7) | C6—C7—H7C | 109.9 (8) |
N1—C4—H4B | 109.7 (7) | H7A—C7—H7C | 109.0 (11) |
H4A—C4—H4B | 109.4 (10) | H7B—C7—H7C | 109.7 (11) |
N1—C4—H4C | 107.2 (7) | | |
| | | |
C2—N2—C1—N1 | 0.25 (10) | N2—C2—C3—N1 | 0.09 (11) |
C2—N2—C1—C5 | −179.19 (8) | C6—O1—C5—O2 | −1.01 (13) |
C3—N1—C1—N2 | −0.20 (10) | C6—O1—C5—C1 | 179.45 (7) |
C4—N1—C1—N2 | −179.26 (9) | N2—C1—C5—O2 | 4.43 (14) |
C3—N1—C1—C5 | 179.20 (8) | N1—C1—C5—O2 | −174.91 (9) |
C4—N1—C1—C5 | 0.14 (15) | N2—C1—C5—O1 | −176.02 (8) |
C1—N2—C2—C3 | −0.20 (11) | N1—C1—C5—O1 | 4.63 (13) |
C1—N1—C3—C2 | 0.06 (10) | C5—O1—C6—C7 | 175.23 (8) |
C4—N1—C3—C2 | 179.20 (8) | | |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.