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The structure of the title compound, C13H10N2O2, comprises a twisted mol­ecule with a dihedral angle of 37.81 (9)°. In the solid state, the mol­ecules exist as typical 2(1H)-pyridone dimers via a hydrogen-bonding interaction from the N-H group to the O atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008863/na6164sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008863/na6164Isup2.hkl
Contains datablock I

CCDC reference: 189406

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.063
  • wR factor = 0.201
  • Data-to-parameter ratio = 15.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(3) - C(31) = 1.43 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO nd COLLECT; data reduction: DENZO nd COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

3-Cyano-6-(4-methoxyphenyl)-2(1H)-pyridone top
Crystal data top
C13H10N2O2F(000) = 472
Mr = 226.23Dx = 1.360 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.6650 (7) ÅCell parameters from 1832 reflections
b = 9.8140 (8) Åθ = 1.0–27.5°
c = 11.1544 (12) ŵ = 0.09 mm1
β = 108.833 (3)°T = 293 K
V = 1104.99 (17) Å3Plate, colourless
Z = 40.30 × 0.10 × 0.03 mm
Data collection top
Bruker-Nonius KappaCCD area-detector
diffractometer
2460 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode906 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.094
Detector resolution: 9.091 pixels mm-1θmax = 27.4°, θmin = 2.3°
φ and ω scansh = 1313
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1112
Tmin = 0.972, Tmax = 0.997l = 1414
4925 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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H atoms treated by a mixture of independent and constrained refinement
S = 0.90 w = 1/[σ2(Fo2) + (0.0831P)2]
where P = (Fo2 + 2Fc2)/3
2460 reflections(Δ/σ)max < 0.001
159 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 4.2083 (0.0133) x + 3.4036 (0.0122) y + 10.4039 (0.0053) z = 3.2471 (0.0091)

* 0.0099 (0.0023) N1 * -0.0040 (0.0023) C2 * -0.0060 (0.0024) C3 * 0.0101 (0.0024) C4 * -0.0046 (0.0024) C5 * -0.0054 (0.0022) C6

Rms deviation of fitted atoms = 0.0071

- 4.2138 (0.0142) x - 2.9541 (0.0138) y + 10.5855 (0.0052) z = 5.2040 (0.0038)

Angle to previous plane (with approximate e.s.d.) = 37.81 (0.09)

* -0.0051 (0.0024) C61 * 0.0127 (0.0024) C62 * -0.0105 (0.0025) C63 * 0.0006 (0.0025) C64 * 0.0069 (0.0027) C65 * -0.0046 (0.0026) C66

Rms deviation of fitted atoms = 0.0078

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.4633 (3)0.1765 (3)0.5582 (3)0.0352 (8)
H10.419 (3)0.103 (3)0.512 (4)0.069 (13)*
C20.5979 (4)0.1595 (3)0.6058 (3)0.0345 (9)
O20.6507 (2)0.0503 (2)0.5884 (2)0.0477 (8)
C30.6697 (3)0.2733 (3)0.6718 (3)0.0336 (9)
C310.8102 (4)0.2589 (3)0.7225 (4)0.0414 (10)
N320.9229 (3)0.2456 (3)0.7617 (4)0.0659 (11)
C40.6054 (4)0.3903 (3)0.6857 (3)0.0424 (10)
H40.65370.46320.73100.053*
C50.4679 (4)0.4008 (3)0.6321 (3)0.0414 (10)
H50.42530.48130.64030.052*
C60.3962 (3)0.2935 (3)0.5679 (3)0.0330 (9)
C610.2522 (3)0.2950 (3)0.5092 (3)0.0352 (9)
C620.1881 (3)0.4135 (3)0.4523 (3)0.0410 (10)
H620.23780.49150.45300.051*
C630.0530 (4)0.4180 (3)0.3951 (4)0.0460 (10)
H630.01290.49720.35480.057*
C640.0229 (4)0.3047 (4)0.3975 (4)0.0430 (10)
C650.0380 (4)0.1875 (4)0.4551 (4)0.0492 (11)
H650.01290.11110.45730.061*
C660.1735 (4)0.1820 (3)0.5095 (4)0.0451 (10)
H660.21320.10140.54700.056*
O640.1559 (3)0.3195 (2)0.3383 (3)0.0601 (8)
C670.2399 (4)0.2070 (4)0.3423 (5)0.0755 (15)
H6710.22640.18220.42880.094*
H6720.33080.23240.30240.094*
H6730.21890.13080.29820.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.038 (2)0.0294 (17)0.035 (2)0.0037 (14)0.0083 (16)0.0034 (14)
C20.037 (2)0.0313 (19)0.034 (2)0.0023 (16)0.0090 (19)0.0008 (16)
O20.0425 (17)0.0352 (13)0.0627 (19)0.0030 (12)0.0134 (14)0.0090 (13)
C30.036 (2)0.0312 (18)0.034 (2)0.0055 (16)0.0119 (19)0.0042 (16)
C310.043 (3)0.035 (2)0.044 (3)0.009 (2)0.012 (2)0.0030 (18)
N320.045 (2)0.068 (2)0.083 (3)0.0061 (19)0.018 (2)0.005 (2)
C40.050 (3)0.0345 (19)0.044 (3)0.0112 (17)0.017 (2)0.0064 (17)
C50.045 (3)0.0300 (19)0.050 (3)0.0006 (17)0.015 (2)0.0055 (17)
C60.040 (2)0.0307 (18)0.031 (2)0.0000 (16)0.0152 (19)0.0000 (16)
C610.038 (2)0.033 (2)0.037 (2)0.0034 (16)0.0160 (19)0.0002 (16)
C620.044 (3)0.035 (2)0.051 (3)0.0005 (17)0.026 (2)0.0042 (18)
C630.046 (3)0.045 (2)0.052 (3)0.0170 (19)0.023 (2)0.0092 (19)
C640.033 (2)0.054 (2)0.045 (3)0.0003 (19)0.016 (2)0.001 (2)
C650.041 (3)0.046 (2)0.062 (3)0.0061 (18)0.019 (2)0.009 (2)
C660.044 (3)0.037 (2)0.053 (3)0.0011 (18)0.014 (2)0.0100 (18)
O640.0344 (18)0.0706 (18)0.074 (2)0.0059 (14)0.0160 (16)0.0051 (16)
C670.038 (3)0.105 (3)0.088 (4)0.008 (3)0.026 (3)0.008 (3)
Geometric parameters (Å, º) top
N1—C21.371 (4)C61—C621.394 (4)
N1—C61.375 (4)C62—C631.375 (4)
N1—H10.92 (4)C62—H620.93
C2—O21.255 (4)C63—C641.380 (4)
C2—C31.419 (4)C63—H630.93
C3—C41.372 (4)C64—O641.366 (4)
C3—C311.427 (5)C64—C651.374 (5)
C31—N321.147 (4)C65—C661.377 (5)
C4—C51.397 (4)C65—H650.93
C4—H40.93C66—H660.93
C5—C61.362 (4)O64—C671.432 (4)
C5—H50.93C67—H6710.96
C6—C611.462 (5)C67—H6720.96
C61—C661.392 (4)C67—H6730.96
C2—N1—C6125.3 (3)C63—C62—C61121.6 (3)
C2—N1—H1114 (2)C63—C62—H62119.2
C6—N1—H1121 (2)C61—C62—H62119.2
O2—C2—N1120.7 (3)C62—C63—C64119.9 (3)
O2—C2—C3124.0 (3)C62—C63—H63120.0
N1—C2—C3115.3 (3)C64—C63—H63120.0
C4—C3—C2120.8 (3)O64—C64—C65125.1 (3)
C4—C3—C31122.5 (3)O64—C64—C63115.4 (3)
C2—C3—C31116.7 (3)C65—C64—C63119.5 (3)
N32—C31—C3178.8 (4)C64—C65—C66120.6 (3)
C3—C4—C5120.5 (3)C64—C65—H65119.7
C3—C4—H4119.8C66—C65—H65119.7
C5—C4—H4119.8C65—C66—C61121.1 (3)
C6—C5—C4120.1 (3)C65—C66—H66119.5
C6—C5—H5120.0C61—C66—H66119.5
C4—C5—H5120.0C64—O64—C67117.8 (3)
C5—C6—N1118.0 (3)O64—C67—H671109.5
C5—C6—C61123.9 (3)O64—C67—H672109.5
N1—C6—C61118.1 (3)H671—C67—H672109.5
C66—C61—C62117.3 (3)O64—C67—H673109.5
C66—C61—C6122.5 (3)H671—C67—H673109.5
C62—C61—C6120.2 (3)H672—C67—H673109.5
C6—N1—C2—O2177.5 (3)C5—C6—C61—C6236.6 (5)
C6—N1—C2—C31.4 (5)N1—C6—C61—C62143.8 (3)
O2—C2—C3—C4179.1 (3)C66—C61—C62—C632.0 (5)
N1—C2—C3—C40.2 (5)C6—C61—C62—C63179.3 (3)
O2—C2—C3—C311.1 (5)C61—C62—C63—C642.5 (5)
N1—C2—C3—C31180.0 (3)C62—C63—C64—O64179.9 (3)
C2—C3—C4—C51.6 (5)C62—C63—C64—C651.3 (5)
C31—C3—C4—C5178.6 (3)O64—C64—C65—C66178.3 (4)
C3—C4—C5—C61.4 (5)C63—C64—C65—C660.3 (6)
C4—C5—C6—N10.1 (5)C64—C65—C66—C610.9 (6)
C4—C5—C6—C61179.7 (3)C62—C61—C66—C650.3 (5)
C2—N1—C6—C51.5 (5)C6—C61—C66—C65179.0 (3)
C2—N1—C6—C61178.8 (3)C65—C64—O64—C673.7 (6)
C5—C6—C61—C66142.1 (4)C63—C64—O64—C67177.6 (3)
N1—C6—C61—C6637.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.92 (4)1.88 (4)2.797 (4)172 (3)
C4—H4···O2ii0.932.533.368 (4)149
C67—H672···N32iii0.962.533.445 (5)160
Symmetry codes: (i) x+1, y, z+1; (ii) x+3/2, y1/2, z+3/2; (iii) x3/2, y1/2, z1/2.
 

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