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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010038/ac2012sup1.cif
Contains datablocks I, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010038/ac2012Isup2.hkl
Contains datablock I

CCDC reference: 605227

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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
C7H10N2O2F(000) = 328
Mr = 154.17Dx = 1.378 Mg m3
Monoclinic, P21/cMelting point = 43–44 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.1040 (8) ÅCell parameters from 5362 reflections
b = 15.2244 (18) Åθ = 2.7–28.0°
c = 7.4511 (9) ŵ = 0.10 mm1
β = 112.797 (2)°T = 100 K
V = 742.92 (15) Å3Plate, colorless
Z = 40.37 × 0.29 × 0.09 mm
Data collection top
Bruker SMART APEX
diffractometer
1728 independent reflections
Radiation source: fine-focus sealed tube1636 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Detector resolution: no pixels mm-1θmax = 28.0°, θmin = 3.1°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
k = 1919
Tmin = 0.960, Tmax = 0.988l = 99
6360 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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068All 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 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
O10.25020 (11)0.57084 (4)0.39888 (9)0.01830 (16)
O20.23052 (11)0.46091 (5)0.59352 (10)0.02000 (17)
N10.24441 (12)0.45189 (5)0.11144 (11)0.01505 (17)
N20.19787 (12)0.34172 (5)0.28830 (12)0.01794 (18)
C10.22529 (13)0.42764 (6)0.28103 (13)0.01515 (19)
C20.20018 (15)0.30936 (7)0.11812 (14)0.0192 (2)
H20.1833 (19)0.2486 (9)0.0843 (18)0.022 (3)*
C30.22843 (14)0.37615 (7)0.00771 (14)0.0180 (2)
H30.2360 (19)0.3774 (8)0.1166 (19)0.022 (3)*
C40.27853 (15)0.53886 (6)0.04420 (14)0.0173 (2)
H4A0.1699 (19)0.5784 (8)0.0380 (17)0.020 (3)*
H4B0.4083 (19)0.5623 (8)0.1334 (18)0.019 (3)*
H4C0.2773 (19)0.5313 (8)0.0873 (19)0.023 (3)*
C50.23488 (13)0.48678 (6)0.44178 (13)0.01523 (19)
C60.25898 (15)0.63570 (6)0.54630 (14)0.0177 (2)
H6A0.3709 (18)0.6192 (7)0.6676 (17)0.015 (3)*
H6B0.1307 (18)0.6334 (8)0.5636 (17)0.017 (3)*
C70.29400 (17)0.72322 (7)0.46991 (15)0.0217 (2)
H7A0.304 (2)0.7695 (10)0.567 (2)0.036 (4)*
H7B0.179 (2)0.7379 (9)0.347 (2)0.028 (3)*
H7C0.421 (2)0.7219 (8)0.4487 (19)0.027 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0256 (4)0.0166 (3)0.0149 (3)0.0012 (3)0.0102 (3)0.0018 (3)
O20.0254 (4)0.0216 (4)0.0146 (3)0.0001 (3)0.0095 (3)0.0010 (3)
N10.0156 (4)0.0169 (4)0.0131 (4)0.0002 (3)0.0059 (3)0.0001 (3)
N20.0186 (4)0.0174 (4)0.0181 (4)0.0004 (3)0.0074 (3)0.0000 (3)
C10.0145 (4)0.0179 (4)0.0132 (4)0.0004 (3)0.0056 (3)0.0014 (3)
C20.0193 (4)0.0182 (5)0.0200 (5)0.0008 (4)0.0077 (4)0.0032 (4)
C30.0177 (4)0.0206 (5)0.0160 (4)0.0000 (4)0.0069 (4)0.0030 (4)
C40.0200 (5)0.0175 (5)0.0157 (4)0.0002 (4)0.0084 (4)0.0020 (3)
C50.0122 (4)0.0186 (5)0.0145 (4)0.0003 (3)0.0046 (3)0.0000 (3)
C60.0214 (5)0.0179 (5)0.0152 (4)0.0003 (4)0.0089 (4)0.0027 (4)
C70.0276 (5)0.0183 (5)0.0211 (5)0.0006 (4)0.0116 (4)0.0002 (4)
Geometric parameters (Å, º) top
O1—C51.3338 (12)C3—H30.948 (13)
O1—C61.4604 (11)C4—H4A0.966 (12)
O2—C51.2089 (12)C4—H4B0.972 (12)
N1—C31.3682 (12)C4—H4C0.983 (13)
N1—C11.3728 (12)C6—C71.5070 (14)
N1—C41.4686 (12)C6—H6A0.977 (12)
N2—C11.3266 (12)C6—H6B0.969 (12)
N2—C21.3664 (13)C7—H7A0.991 (15)
C1—C51.4787 (13)C7—H7B0.988 (14)
C2—C31.3707 (14)C7—H7C0.974 (13)
C2—H20.954 (13)
C5—O1—C6116.89 (7)H4A—C4—H4C109.1 (10)
C3—N1—C1106.09 (8)H4B—C4—H4C111.4 (10)
C3—N1—C4123.76 (8)O2—C5—O1124.81 (9)
C1—N1—C4130.15 (8)O2—C5—C1123.32 (9)
C1—N2—C2105.24 (8)O1—C5—C1111.87 (8)
N2—C1—N1111.79 (8)O1—C6—C7106.20 (8)
N2—C1—C5121.92 (8)O1—C6—H6A107.7 (7)
N1—C1—C5126.29 (8)C7—C6—H6A112.5 (7)
N2—C2—C3110.28 (9)O1—C6—H6B107.9 (7)
N2—C2—H2123.3 (8)C7—C6—H6B112.5 (7)
C3—C2—H2126.4 (8)H6A—C6—H6B109.7 (10)
N1—C3—C2106.59 (8)C6—C7—H7A109.2 (8)
N1—C3—H3120.7 (8)C6—C7—H7B110.7 (8)
C2—C3—H3132.7 (8)H7A—C7—H7B108.2 (11)
N1—C4—H4A110.1 (7)C6—C7—H7C109.9 (8)
N1—C4—H4B109.7 (7)H7A—C7—H7C109.0 (11)
H4A—C4—H4B109.4 (10)H7B—C7—H7C109.7 (11)
N1—C4—H4C107.2 (7)
C2—N2—C1—N10.25 (10)N2—C2—C3—N10.09 (11)
C2—N2—C1—C5179.19 (8)C6—O1—C5—O21.01 (13)
C3—N1—C1—N20.20 (10)C6—O1—C5—C1179.45 (7)
C4—N1—C1—N2179.26 (9)N2—C1—C5—O24.43 (14)
C3—N1—C1—C5179.20 (8)N1—C1—C5—O2174.91 (9)
C4—N1—C1—C50.14 (15)N2—C1—C5—O1176.02 (8)
C1—N2—C2—C30.20 (11)N1—C1—C5—O14.63 (13)
C1—N1—C3—C20.06 (10)C5—O1—C6—C7175.23 (8)
C4—N1—C3—C2179.20 (8)
 

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