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The title compound, C7H10N2O3, is planar and the structure is stabilized by an intramolecular N—H...O hydrogen bond. The molecules form dimers through N—H...O hydrogen bonds that are linked by N—H...N hydrogen bonds along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033720/is6029sup1.cif
Contains datablocks I, global, publication_text

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033720/is6029Isup2.hkl
Contains datablock I

CCDC reference: 262496

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.063
  • wR factor = 0.151
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003), ORTEP-3 (Farrugia, 1997) and ZORTEP (Zsolnai, 1998); software used to prepare material for publication: PLATON).

Ethyl 5-amino-3-methylisoxazole-4-carboxylate top
Crystal data top
C7H10N2O3F(000) = 720
Mr = 170.17Dx = 1.256 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 12.642 (2) ÅCell parameters from 7495 reflections
b = 8.5036 (14) Åθ = 2.4–28.0°
c = 16.934 (3) ŵ = 0.10 mm1
β = 98.488 (3)°T = 293 K
V = 1800.5 (5) Å3Rectangular block, colourless
Z = 80.27 × 0.25 × 0.22 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
1494 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 28.0°, θmin = 2.4°
ω scansh = 1616
7495 measured reflectionsk = 1111
2070 independent reflectionsl = 1822
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0647P)2 + 0.5335P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.002
2070 reflectionsΔρmax = 0.17 e Å3
118 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (2)
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
O10.28749 (12)0.02256 (17)0.72332 (8)0.0635 (5)
N20.34153 (17)0.1718 (2)0.72526 (11)0.0669 (6)
C30.36504 (17)0.1934 (2)0.65390 (12)0.0520 (5)
C40.33008 (15)0.0665 (2)0.60223 (10)0.0461 (5)
C50.28213 (16)0.0360 (2)0.64941 (11)0.0501 (5)
C60.33702 (15)0.0365 (2)0.51946 (11)0.0488 (5)
O70.30062 (14)0.07946 (18)0.48428 (8)0.0741 (5)
O80.38831 (12)0.14872 (16)0.48511 (8)0.0581 (4)
C90.40024 (19)0.1253 (3)0.40226 (12)0.0670 (6)
H9A0.33060.11760.36960.080*
H9B0.43940.02900.39620.080*
C100.4601 (3)0.2635 (3)0.37725 (17)0.0953 (9)
H10A0.46960.25160.32240.143*
H10B0.52870.26980.41000.143*
H10C0.42040.35780.38330.143*
N110.23454 (18)0.1727 (2)0.63567 (13)0.0686 (6)
C120.4208 (2)0.3405 (3)0.63647 (14)0.0720 (7)
H12A0.43370.40390.68380.108*
H12B0.37710.39790.59510.108*
H12C0.48780.31480.61920.108*
H11A0.2092 (19)0.223 (3)0.6722 (15)0.071 (7)*
H11B0.2342 (19)0.215 (3)0.5901 (17)0.079 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0937 (12)0.0609 (9)0.0397 (8)0.0035 (8)0.0227 (7)0.0055 (6)
N20.0938 (15)0.0579 (11)0.0503 (11)0.0068 (10)0.0146 (10)0.0124 (8)
C30.0611 (13)0.0498 (11)0.0448 (11)0.0029 (9)0.0067 (9)0.0035 (8)
C40.0543 (12)0.0459 (10)0.0388 (10)0.0003 (8)0.0089 (8)0.0006 (8)
C50.0650 (13)0.0511 (11)0.0357 (10)0.0028 (9)0.0123 (9)0.0003 (8)
C60.0578 (12)0.0498 (10)0.0399 (10)0.0014 (9)0.0111 (9)0.0033 (8)
O70.1161 (14)0.0649 (10)0.0442 (9)0.0279 (9)0.0211 (8)0.0107 (7)
O80.0712 (10)0.0618 (9)0.0437 (8)0.0092 (7)0.0163 (7)0.0053 (6)
C90.0717 (15)0.0882 (16)0.0451 (12)0.0068 (12)0.0219 (11)0.0115 (11)
C100.104 (2)0.101 (2)0.091 (2)0.0071 (17)0.0481 (17)0.0375 (16)
N110.1075 (17)0.0591 (11)0.0451 (11)0.0203 (11)0.0304 (11)0.0020 (9)
C120.0864 (18)0.0604 (13)0.0679 (15)0.0157 (12)0.0069 (13)0.0088 (11)
Geometric parameters (Å, º) top
O1—C51.339 (2)C9—C101.492 (3)
O1—N21.439 (2)C9—H9A0.9700
N2—C31.299 (3)C9—H9B0.9700
C3—C41.418 (2)C10—H10A0.9600
C3—C121.487 (3)C10—H10B0.9600
C4—C51.381 (3)C10—H10C0.9600
C4—C61.440 (3)N11—H11A0.85 (3)
C5—N111.314 (3)N11—H11B0.85 (3)
C6—O71.207 (2)C12—H12A0.9600
C6—O81.335 (2)C12—H12B0.9600
O8—C91.447 (2)C12—H12C0.9600
C5—O1—N2107.90 (14)O8—C9—H9B110.3
C3—N2—O1106.04 (15)C10—C9—H9B110.3
N2—C3—C4111.90 (18)H9A—C9—H9B108.5
N2—C3—C12118.94 (18)C9—C10—H10A109.5
C4—C3—C12129.15 (19)C9—C10—H10B109.5
C5—C4—C3104.27 (17)H10A—C10—H10B109.5
C5—C4—C6123.08 (17)C9—C10—H10C109.5
C3—C4—C6132.65 (17)H10A—C10—H10C109.5
N11—C5—O1116.93 (18)H10B—C10—H10C109.5
N11—C5—C4133.19 (18)C5—N11—H11A121.8 (16)
O1—C5—C4109.88 (17)C5—N11—H11B118.5 (17)
O7—C6—O8122.91 (18)H11A—N11—H11B120 (2)
O7—C6—C4123.49 (17)C3—C12—H12A109.5
O8—C6—C4113.61 (16)C3—C12—H12B109.5
C6—O8—C9116.80 (16)H12A—C12—H12B109.5
O8—C9—C10107.2 (2)C3—C12—H12C109.5
O8—C9—H9A110.3H12A—C12—H12C109.5
C10—C9—H9A110.3H12B—C12—H12C109.5
C5—O1—N2—C30.1 (2)C6—C4—C5—N110.2 (4)
O1—N2—C3—C40.0 (2)C3—C4—C5—O10.2 (2)
O1—N2—C3—C12179.20 (18)C6—C4—C5—O1179.97 (17)
N2—C3—C4—C50.1 (2)C5—C4—C6—O70.9 (3)
C12—C3—C4—C5179.0 (2)C3—C4—C6—O7178.9 (2)
N2—C3—C4—C6179.9 (2)C5—C4—C6—O8178.73 (17)
C12—C3—C4—C60.8 (4)C3—C4—C6—O81.5 (3)
N2—O1—C5—N11179.66 (18)O7—C6—O8—C90.7 (3)
N2—O1—C5—C40.2 (2)C4—C6—O8—C9178.88 (17)
C3—C4—C5—N11179.6 (2)C6—O8—C9—C10179.55 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···N2i0.85 (3)2.14 (3)2.981 (3)172 (2)
N11—H11B···O7ii0.85 (3)2.16 (3)2.915 (2)148 (2)
N11—H11B···O70.85 (3)2.39 (3)2.921 (3)122 (2)
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x+1/2, y1/2, z+1.
 

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