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X-ray diffraction study of the title compound, C11H11NO2, (I), has shown that the molecular geometry is similar to that of 1-ethyl-4-hydroxy-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ic acid, (II) [Shishkina, Shishkin, Ukrainets, Dakkah & Sidorenko (2002). Acta Cryst. E58, o254-o256]. Observed elongations of the bonds around the N atom are caused by steric hindrance between the ethyl H atoms and the planar quinolone fragment. Exocyclic angles in the 4-position are also distorted, but, in contrast to (II), this distortion is caused by the formation of zigzag hydrogen-bonded chains along the [010] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029241/hg6109sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029241/hg6109Isup2.hkl
Contains datablock I

CCDC reference: 259590

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.103
  • Data-to-parameter ratio = 8.9

checkCIF/PLATON results

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Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.45 From the CIF: _reflns_number_total 1131 Count of symmetry unique reflns 1139 Completeness (_total/calc) 99.30% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: P3 (Siemens,1989); cell refinement: P3; data reduction: XDISK and XPREP (Siemens, 1991); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C11H11NO2F(000) = 400
Mr = 189.21Dx = 1.348 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 24 reflections
a = 7.8474 (12) Åθ = 11.0–12.0°
b = 8.4660 (14) ŵ = 0.09 mm1
c = 14.033 (3) ÅT = 293 K
V = 932.3 (3) Å3Polyhedron, colourless
Z = 40.35 × 0.3 × 0.3 mm
Data collection top
Siemens P3/PC
diffractometer
θmax = 26.5°, θmin = 2.8°
2θ/θ scansh = 09
1226 measured reflectionsk = 010
1131 independent reflectionsl = 017
974 reflections with I > 2σ(I)2 standard reflections every 98 reflections
Rint = 0.016 intensity decay: 1%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0774P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max < 0.001
S = 0.97Δρmax = 0.13 e Å3
1131 reflectionsΔρmin = 0.13 e Å3
127 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.53866 (18)1.11314 (17)0.13981 (9)0.0505 (4)
O20.74016 (19)0.62483 (17)0.26303 (10)0.0541 (4)
H20.64730.62190.28980.065*
N10.79890 (18)1.02257 (18)0.09523 (10)0.0369 (4)
C20.6498 (2)1.0060 (2)0.14664 (13)0.0388 (4)
C30.6284 (2)0.8687 (2)0.20415 (13)0.0401 (4)
H30.52750.85560.23790.048*
C40.7513 (2)0.7569 (2)0.21091 (12)0.0376 (4)
C4A0.9112 (2)0.7775 (2)0.16043 (12)0.0339 (4)
C51.0444 (3)0.6677 (2)0.16819 (13)0.0416 (4)
H51.03040.57830.20590.05*
C61.1953 (3)0.6910 (3)0.12064 (14)0.0469 (5)
H61.28310.61790.12630.056*
C71.2161 (3)0.8242 (3)0.06404 (14)0.0467 (5)
H71.31830.83970.03180.056*
C81.0876 (2)0.9334 (2)0.05499 (14)0.0421 (5)
H81.10381.02190.01680.051*
C8A0.9317 (2)0.9127 (2)0.10297 (12)0.0341 (4)
C90.8166 (3)1.1655 (2)0.03641 (14)0.0423 (5)
H9A0.70581.19460.01130.051*
H9B0.89071.14260.01720.051*
C100.8888 (3)1.3028 (2)0.09170 (16)0.0495 (5)
H10A0.89961.39270.05040.074*
H10B0.99891.27490.11630.074*
H10C0.81391.32830.14360.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0455 (7)0.0487 (8)0.0572 (8)0.0119 (7)0.0070 (7)0.0034 (7)
O20.0469 (8)0.0493 (8)0.0661 (8)0.0001 (7)0.0127 (7)0.0212 (8)
N10.0367 (7)0.0356 (8)0.0383 (7)0.0008 (7)0.0023 (6)0.0010 (7)
C20.0367 (9)0.0375 (9)0.0422 (9)0.0006 (8)0.0007 (7)0.0051 (9)
C30.0331 (8)0.0449 (10)0.0423 (9)0.0035 (9)0.0067 (8)0.0003 (8)
C40.0405 (9)0.0354 (9)0.0368 (8)0.0052 (9)0.0003 (7)0.0000 (8)
C4A0.0362 (9)0.0316 (8)0.0338 (8)0.0043 (7)0.0008 (7)0.0042 (7)
C50.0477 (10)0.0363 (9)0.0408 (8)0.0026 (9)0.0014 (9)0.0016 (8)
C60.0414 (10)0.0456 (10)0.0538 (11)0.0097 (10)0.0030 (9)0.0086 (9)
C70.0417 (10)0.0486 (11)0.0498 (10)0.0008 (9)0.0127 (9)0.0089 (10)
C80.0453 (10)0.0368 (10)0.0444 (9)0.0054 (9)0.0097 (8)0.0053 (8)
C8A0.0378 (9)0.0336 (9)0.0309 (8)0.0032 (8)0.0002 (7)0.0074 (7)
C90.0441 (10)0.0405 (10)0.0425 (9)0.0026 (9)0.0027 (9)0.0074 (8)
C100.0546 (11)0.0391 (10)0.0548 (11)0.0016 (10)0.0017 (11)0.0026 (10)
Geometric parameters (Å, º) top
O1—C21.262 (2)C5—H50.93
O2—C41.339 (2)C6—C71.389 (3)
O2—H20.82C6—H60.93
N1—C21.382 (2)C7—C81.374 (3)
N1—C8A1.402 (2)C7—H70.93
N1—C91.471 (2)C8—C8A1.407 (3)
C2—C31.425 (3)C8—H80.93
C3—C41.355 (3)C9—C101.509 (3)
C3—H30.93C9—H9A0.97
C4—C4A1.452 (2)C9—H9B0.97
C4A—C51.403 (3)C10—H10A0.96
C4A—C8A1.409 (2)C10—H10B0.96
C5—C61.373 (3)C10—H10C0.96
C4—O2—H2109.5C8—C7—C6120.87 (18)
C2—N1—C8A121.46 (15)C8—C7—H7119.6
C2—N1—C9117.17 (15)C6—C7—H7119.6
C8A—N1—C9121.27 (14)C7—C8—C8A120.64 (18)
O1—C2—N1118.20 (16)C7—C8—H8119.7
O1—C2—C3123.22 (17)C8A—C8—H8119.7
N1—C2—C3118.58 (16)N1—C8A—C8121.77 (16)
C4—C3—C2121.75 (17)N1—C8A—C4A119.90 (15)
C4—C3—H3119.1C8—C8A—C4A118.33 (17)
C2—C3—H3119.1N1—C9—C10112.39 (15)
O2—C4—C3125.16 (17)N1—C9—H9A109.1
O2—C4—C4A115.04 (16)C10—C9—H9A109.1
C3—C4—C4A119.80 (16)N1—C9—H9B109.1
C5—C4A—C8A119.80 (16)C10—C9—H9B109.1
C5—C4A—C4121.80 (16)H9A—C9—H9B107.9
C8A—C4A—C4118.40 (16)C9—C10—H10A109.5
C6—C5—C4A120.64 (18)C9—C10—H10B109.5
C6—C5—H5119.7H10A—C10—H10B109.5
C4A—C5—H5119.7C9—C10—H10C109.5
C5—C6—C7119.72 (19)H10A—C10—H10C109.5
C5—C6—H6120.1H10B—C10—H10C109.5
C7—C6—H6120.1
C8A—N1—C2—O1176.66 (16)C5—C6—C7—C80.1 (3)
C9—N1—C2—O10.3 (2)C6—C7—C8—C8A0.0 (3)
C8A—N1—C2—C33.8 (2)C2—N1—C8A—C8176.36 (16)
C9—N1—C2—C3179.85 (16)C9—N1—C8A—C80.1 (2)
O1—C2—C3—C4179.11 (18)C2—N1—C8A—C4A3.3 (2)
N1—C2—C3—C41.3 (3)C9—N1—C8A—C4A179.57 (15)
C2—C3—C4—O2179.71 (17)C7—C8—C8A—N1179.76 (16)
C2—C3—C4—C4A1.5 (3)C7—C8—C8A—C4A0.1 (3)
O2—C4—C4A—C51.4 (2)C5—C4A—C8A—N1179.91 (16)
C3—C4—C4A—C5177.55 (17)C4—C4A—C8A—N10.4 (2)
O2—C4—C4A—C8A179.17 (15)C5—C4A—C8A—C80.2 (2)
C3—C4—C4A—C8A1.9 (2)C4—C4A—C8A—C8179.25 (16)
C8A—C4A—C5—C60.3 (3)C2—N1—C9—C1086.8 (2)
C4—C4A—C5—C6179.17 (17)C8A—N1—C9—C1089.6 (2)
C4A—C5—C6—C70.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.762.580 (2)173
Symmetry code: (i) x+1, y1/2, z+1/2.
 

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