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The structure of 2,6-di­methyl­quinolin-4(1H)-one, C11H11NO, has been determined as part of our study on the synthesis and crystallography of quinoline and quinazoline derivatives. It crystallizes in the monoclinic space group P21/c. The mol­ecule is planar, with the dihedral angle between the planes of the two rings being 2 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023249/wn6185sup1.cif
Contains datablocks rkdes13, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023249/wn6185Isup2.hkl
Contains datablock I

CCDC reference: 227001

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.134
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low .............. 24.97 Deg.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995).

2,6-dimethylquinolin-4(1H)-one top
Crystal data top
C11H11NOF(000) = 368
Mr = 173.21Dx = 1.243 Mg m3
Monoclinic, P21/cMelting point: 533 K
Hall symbol: -P2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.068 (7) ÅCell parameters from 25 reflections
b = 8.352 (3) Åθ = 6.2–11.5°
c = 12.253 (5) ŵ = 0.08 mm1
β = 94.15 (4)°T = 293 K
V = 925.6 (9) Å3Plate-like, yellow
Z = 40.4 × 0.3 × 0.1 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.009
Radiation source: fine-focus sealed tube, Laboratory X-ray Generatorθmax = 25.0°, θmin = 2.3°
Graphite monochromatorh = 010
ω/2θ scansk = 09
1737 measured reflectionsl = 1414
1629 independent reflections2 standard reflections every 60 min
1306 reflections with I > 2σ(I) intensity decay: <2%
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.135 w = 1/[σ2(Fo2) + (0.0684P)2 + 0.2584P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1629 reflectionsΔρmax = 0.24 e Å3
121 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, fc*=kfc[1+0.001xfc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (5)
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
O10.71725 (14)0.42824 (15)0.03411 (9)0.0533 (4)
N10.71513 (14)0.20258 (17)0.26042 (11)0.0432 (4)
H10.71360.15560.32280.052*
C20.59707 (18)0.2905 (2)0.22294 (14)0.0441 (4)
C30.59554 (18)0.3650 (2)0.12367 (14)0.0457 (4)
H30.51180.42230.09880.055*
C40.71705 (18)0.3583 (2)0.05716 (12)0.0406 (4)
C50.97234 (18)0.2492 (2)0.04407 (13)0.0439 (4)
H50.97690.30180.02250.053*
C61.09121 (19)0.1596 (2)0.08344 (15)0.0473 (5)
C71.08045 (19)0.0802 (2)0.18367 (15)0.0520 (5)
H71.15970.01830.21150.062*
C80.95775 (19)0.0909 (2)0.24175 (14)0.0481 (5)
H80.95340.03560.30730.058*
C90.83806 (17)0.18606 (19)0.20141 (12)0.0390 (4)
C100.84381 (17)0.26447 (19)0.10086 (12)0.0382 (4)
C111.2274 (2)0.1455 (3)0.02081 (18)0.0648 (6)
H11a1.19900.12230.05450.097*
H11b1.28880.06070.05130.097*
H11c1.28120.24450.02570.097*
C120.4717 (2)0.3012 (3)0.29634 (18)0.0631 (6)
H12a0.44080.19530.31490.095*
H12b0.39040.35720.25910.095*
H12c0.50390.35800.36190.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0615 (8)0.0603 (8)0.0378 (6)0.0120 (6)0.0018 (5)0.0052 (6)
N10.0448 (8)0.0476 (8)0.0377 (7)0.0007 (6)0.0066 (6)0.0035 (6)
C20.0396 (9)0.0452 (9)0.0478 (10)0.0013 (7)0.0061 (7)0.0036 (8)
C30.0390 (9)0.0500 (10)0.0474 (9)0.0046 (7)0.0008 (7)0.0015 (8)
C40.0455 (9)0.0411 (9)0.0344 (8)0.0010 (7)0.0016 (7)0.0045 (6)
C50.0469 (10)0.0474 (10)0.0377 (8)0.0005 (8)0.0058 (7)0.0024 (7)
C60.0415 (9)0.0475 (10)0.0531 (10)0.0011 (7)0.0054 (7)0.0092 (8)
C70.0438 (10)0.0534 (11)0.0580 (11)0.0124 (8)0.0005 (8)0.0000 (8)
C80.0504 (10)0.0504 (10)0.0433 (9)0.0080 (8)0.0006 (8)0.0050 (8)
C90.0395 (9)0.0395 (9)0.0380 (8)0.0002 (7)0.0028 (7)0.0040 (7)
C100.0403 (9)0.0391 (9)0.0351 (8)0.0002 (7)0.0009 (6)0.0053 (6)
C110.0475 (11)0.0724 (14)0.0762 (14)0.0037 (10)0.0158 (10)0.0114 (11)
C120.0512 (11)0.0705 (13)0.0701 (13)0.0058 (10)0.0210 (10)0.0061 (10)
Geometric parameters (Å, º) top
O1—C41.2618 (19)C6—C111.505 (3)
N1—C21.351 (2)C7—C81.366 (3)
N1—C91.379 (2)C7—H70.9300
N1—H10.8600C8—C91.406 (2)
C2—C31.366 (2)C8—H80.9300
C2—C121.502 (3)C9—C101.400 (2)
C3—C41.418 (2)C11—H11a0.9600
C3—H30.9300C11—H11b0.9600
C4—C101.461 (2)C11—H11c0.9600
C5—C61.371 (2)C12—H12a0.9600
C5—C101.406 (2)C12—H12b0.9600
C5—H50.9300C12—H12c0.9600
C6—C71.405 (3)
C2—N1—C9121.81 (14)C7—C8—C9119.38 (16)
C2—N1—H1119.1C7—C8—H8120.3
C9—N1—H1119.1C9—C8—H8120.3
N1—C2—C3120.48 (15)N1—C9—C10119.86 (14)
N1—C2—C12116.38 (16)N1—C9—C8120.34 (15)
C3—C2—C12123.13 (17)C10—C9—C8119.80 (15)
C2—C3—C4122.37 (16)C9—C10—C5118.58 (15)
C2—C3—H3118.8C9—C10—C4119.69 (15)
C4—C3—H3118.8C5—C10—C4121.73 (15)
O1—C4—C3122.82 (15)C6—C11—H11a109.5
O1—C4—C10121.44 (15)C6—C11—H11b109.5
C3—C4—C10115.74 (15)H11a—C11—H11b109.5
C6—C5—C10122.28 (16)C6—C11—H11c109.5
C6—C5—H5118.9H11a—C11—H11c109.5
C10—C5—H5118.9H11b—C11—H11c109.5
C5—C6—C7117.55 (16)C2—C12—H12a109.5
C5—C6—C11121.09 (17)C2—C12—H12b109.5
C7—C6—C11121.36 (17)H12a—C12—H12b109.5
C8—C7—C6122.37 (16)C2—C12—H12c109.5
C8—C7—H7118.8H12a—C12—H12c109.5
C6—C7—H7118.8H12b—C12—H12c109.5
C9—N1—C2—C30.7 (2)C7—C8—C9—N1177.91 (16)
C9—N1—C2—C12178.84 (16)C7—C8—C9—C102.1 (2)
N1—C2—C3—C41.8 (3)N1—C9—C10—C5178.15 (15)
C12—C2—C3—C4177.69 (17)C8—C9—C10—C51.8 (2)
C2—C3—C4—O1179.21 (16)N1—C9—C10—C42.4 (2)
C2—C3—C4—C100.8 (2)C8—C9—C10—C4177.66 (15)
C10—C5—C6—C70.6 (3)C6—C5—C10—C90.5 (2)
C10—C5—C6—C11179.98 (16)C6—C5—C10—C4179.02 (15)
C5—C6—C7—C80.4 (3)O1—C4—C10—C9178.72 (14)
C11—C6—C7—C8179.78 (18)C3—C4—C10—C91.3 (2)
C6—C7—C8—C90.9 (3)O1—C4—C10—C50.8 (2)
C2—N1—C9—C101.4 (2)C3—C4—C10—C5179.25 (15)
C2—N1—C9—C8178.62 (15)
 

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