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The title compound, C14H13NO5, exhibits a resonance-assisted hydrogen bond O—H...O=C [2.505 (4) Å], which leads to a lengthening of the carbonyl C=O bond, a shortening of the C—OH bond and delocalization of the electron density within the dihydro­pyridine ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805037463/kp6069sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805037463/kp6069Isup2.hkl
Contains datablock I

CCDC reference: 293938

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.049
  • wR factor = 0.138
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 2 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: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: SHELXL97.

Methyl 1-acetonyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate top
Crystal data top
C14H13NO5F(000) = 576
Mr = 275.25Dx = 1.425 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybcCell parameters from 12 reflections
a = 11.084 (4) Åθ = 2–25°
b = 15.120 (5) ŵ = 0.11 mm1
c = 8.133 (3) ÅT = 293 K
β = 109.77 (3)°Plate, colourless
V = 1282.7 (8) Å30.40 × 0.20 × 0.20 mm
Z = 4
Data collection top
Siemens P3/PC
diffractometer
Rint = 0.069
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 2.0°
Graphite monochromatorh = 1312
ω–2θ scansk = 180
2406 measured reflectionsl = 09
2238 independent reflections2 standard reflections every 98 reflections
857 reflections with I > 2σ(I) intensity decay: 5%
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0631P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max < 0.001
2238 reflectionsΔρmax = 0.17 e Å3
185 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0044 (13)
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
N10.3973 (2)0.6718 (2)0.0847 (3)0.0402 (8)
C10.3563 (3)0.7574 (2)0.0954 (4)0.0424 (10)
O10.3812 (2)0.52387 (17)0.1113 (4)0.0651 (9)
O20.0598 (2)0.71380 (18)0.1722 (4)0.0700 (9)
H2O0.02910.66740.19220.105*
C20.4280 (4)0.8300 (3)0.0789 (4)0.0553 (11)
H20.50500.82150.05890.066*
O30.0352 (2)0.55035 (19)0.1995 (4)0.0700 (9)
C30.3860 (5)0.9144 (3)0.0920 (5)0.0665 (13)
H30.43480.96260.08080.080*
O40.1956 (2)0.46152 (18)0.2068 (3)0.0632 (8)
C40.2727 (5)0.9283 (3)0.1213 (5)0.0700 (13)
H40.24500.98560.12960.084*
C50.2009 (4)0.8583 (3)0.1382 (5)0.0612 (12)
H50.12390.86800.15760.073*
O50.6342 (2)0.67652 (19)0.3442 (4)0.0686 (9)
C60.2422 (3)0.7712 (2)0.1265 (5)0.0445 (10)
C70.1695 (3)0.6971 (3)0.1468 (5)0.0483 (10)
C80.2147 (3)0.6118 (2)0.1475 (4)0.0415 (9)
C90.3341 (3)0.5963 (3)0.1141 (5)0.0439 (9)
C100.1411 (4)0.5399 (3)0.1835 (5)0.0513 (10)
C110.1276 (4)0.3896 (3)0.2520 (7)0.0998 (18)
H11A0.04910.37890.15760.150*
H11B0.10880.40460.35550.150*
H11C0.17970.33730.27320.150*
C120.5136 (3)0.6553 (2)0.0440 (4)0.0462 (10)
H12B0.51750.69720.04440.055*
H12A0.50860.59640.00540.055*
C130.6354 (3)0.6624 (2)0.1989 (5)0.0446 (9)
C140.7553 (3)0.6508 (2)0.1574 (5)0.0608 (11)
H14A0.75310.59480.10070.091*
H14B0.82780.65250.26350.091*
H14C0.76230.69750.08130.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0312 (16)0.053 (2)0.0397 (19)0.0038 (15)0.0155 (16)0.0036 (16)
C10.041 (2)0.047 (3)0.036 (2)0.002 (2)0.009 (2)0.0008 (19)
O10.0575 (18)0.0483 (18)0.097 (2)0.0129 (15)0.0364 (18)0.0009 (16)
O20.0434 (17)0.080 (2)0.096 (2)0.0146 (15)0.0358 (17)0.003 (2)
C20.062 (3)0.063 (3)0.040 (2)0.007 (2)0.016 (2)0.002 (2)
O30.0402 (17)0.092 (2)0.083 (2)0.0078 (15)0.0277 (16)0.0004 (17)
C30.091 (4)0.055 (3)0.047 (3)0.013 (3)0.014 (3)0.002 (2)
O40.0543 (17)0.0568 (19)0.078 (2)0.0060 (16)0.0212 (16)0.0135 (17)
C40.103 (4)0.041 (3)0.063 (3)0.012 (3)0.024 (3)0.002 (2)
C50.069 (3)0.056 (3)0.057 (3)0.014 (3)0.019 (2)0.004 (2)
O50.0513 (18)0.106 (2)0.0484 (17)0.0154 (16)0.0167 (15)0.0058 (17)
C60.045 (2)0.043 (3)0.042 (2)0.004 (2)0.010 (2)0.007 (2)
C70.031 (2)0.065 (3)0.045 (2)0.009 (2)0.0089 (19)0.001 (2)
C80.030 (2)0.049 (3)0.043 (2)0.001 (2)0.0077 (18)0.001 (2)
C90.035 (2)0.053 (3)0.042 (2)0.000 (2)0.0110 (19)0.003 (2)
C100.041 (2)0.056 (3)0.052 (3)0.000 (2)0.009 (2)0.000 (2)
C110.091 (4)0.090 (4)0.115 (5)0.030 (3)0.030 (4)0.026 (3)
C120.045 (2)0.058 (3)0.042 (2)0.0052 (19)0.023 (2)0.007 (2)
C130.038 (2)0.044 (2)0.056 (3)0.0007 (17)0.021 (2)0.002 (2)
C140.040 (2)0.065 (3)0.085 (3)0.0035 (19)0.032 (2)0.002 (2)
Geometric parameters (Å, º) top
N1—C11.385 (4)C5—C61.408 (5)
N1—C91.402 (4)C5—H50.9300
N1—C121.457 (4)O5—C131.205 (4)
C1—C61.386 (4)C6—C71.422 (5)
C1—C21.388 (5)C7—C81.384 (5)
O1—C91.216 (4)C8—C101.447 (5)
O2—C71.324 (4)C8—C91.457 (5)
O2—H2O0.8200C11—H11A0.9600
C2—C31.375 (5)C11—H11B0.9600
C2—H20.9300C11—H11C0.9600
O3—C101.234 (4)C12—C131.507 (5)
C3—C41.370 (5)C12—H12B0.9700
C3—H30.9300C12—H12A0.9700
O4—C101.315 (4)C13—C141.488 (4)
O4—C111.440 (4)C14—H14A0.9600
C4—C51.358 (5)C14—H14B0.9600
C4—H40.9300C14—H14C0.9600
C1—N1—C9123.9 (3)C10—C8—C9121.8 (4)
C1—N1—C12120.6 (3)O1—C9—N1119.2 (3)
C9—N1—C12115.5 (3)O1—C9—C8124.8 (4)
N1—C1—C6119.4 (3)N1—C9—C8116.0 (4)
N1—C1—C2121.5 (3)O3—C10—O4120.4 (4)
C6—C1—C2119.1 (4)O3—C10—C8123.2 (4)
C7—O2—H2O109.5O4—C10—C8116.3 (3)
C3—C2—C1120.4 (4)O4—C11—H11A109.5
C3—C2—H2119.8O4—C11—H11B109.5
C1—C2—H2119.8H11A—C11—H11B109.5
C4—C3—C2120.6 (4)O4—C11—H11C109.5
C4—C3—H3119.7H11A—C11—H11C109.5
C2—C3—H3119.7H11B—C11—H11C109.5
C10—O4—C11117.6 (3)N1—C12—C13114.1 (3)
C5—C4—C3120.1 (4)N1—C12—H12B108.7
C5—C4—H4119.9C13—C12—H12B108.7
C3—C4—H4119.9N1—C12—H12A108.7
C4—C5—C6120.4 (4)C13—C12—H12A108.7
C4—C5—H5119.8H12B—C12—H12A107.6
C6—C5—H5119.8O5—C13—C14123.4 (4)
C1—C6—C5119.4 (4)O5—C13—C12121.9 (3)
C1—C6—C7119.4 (3)C14—C13—C12114.7 (3)
C5—C6—C7121.2 (4)C13—C14—H14A109.5
O2—C7—C8121.8 (4)C13—C14—H14B109.5
O2—C7—C6117.0 (3)H14A—C14—H14B109.5
C8—C7—C6121.1 (3)C13—C14—H14C109.5
C7—C8—C10118.2 (3)H14A—C14—H14C109.5
C7—C8—C9120.0 (3)H14B—C14—H14C109.5
C9—N1—C1—C64.1 (5)O2—C7—C8—C9178.3 (3)
C12—N1—C1—C6177.1 (3)C6—C7—C8—C94.6 (5)
C9—N1—C1—C2174.7 (3)C1—N1—C9—O1175.9 (3)
C12—N1—C1—C24.1 (5)C12—N1—C9—O13.0 (5)
N1—C1—C2—C3179.3 (3)C1—N1—C9—C83.6 (5)
C6—C1—C2—C30.5 (5)C12—N1—C9—C8177.4 (3)
C1—C2—C3—C40.1 (6)C7—C8—C9—O1179.7 (4)
C2—C3—C4—C50.2 (6)C10—C8—C9—O10.9 (6)
C3—C4—C5—C60.2 (6)C7—C8—C9—N10.7 (5)
N1—C1—C6—C5179.7 (3)C10—C8—C9—N1178.7 (3)
C2—C1—C6—C50.9 (5)C11—O4—C10—O30.4 (6)
N1—C1—C6—C70.0 (5)C11—O4—C10—C8176.8 (3)
C2—C1—C6—C7178.8 (3)C7—C8—C10—O36.1 (5)
C4—C5—C6—C10.8 (5)C9—C8—C10—O3174.5 (4)
C4—C5—C6—C7178.9 (4)C7—C8—C10—O4170.9 (3)
C1—C6—C7—O2178.5 (3)C9—C8—C10—O48.5 (5)
C5—C6—C7—O21.9 (5)C1—N1—C12—C1382.2 (4)
C1—C6—C7—C84.3 (5)C9—N1—C12—C1396.8 (3)
C5—C6—C7—C8175.4 (4)N1—C12—C13—O53.2 (5)
O2—C7—C8—C102.3 (5)N1—C12—C13—C14176.6 (3)
C6—C7—C8—C10174.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O30.821.772.505 (4)148
 

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