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The mol­ecule of the title compound, C14H13NO3, adopts the keto–amine tautomeric form. An intra­molecular N—H...O hydrogen bond dictates the essentially planar mol­ecular geometry; the two benzene rings make a dihedral angle of 7.93 (7)°. The crystal packing is stabilized by inter­molecular O—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501319X/cv6500sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501319X/cv6500Isup2.hkl
Contains datablock I

CCDC reference: 274378

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.038
  • wR factor = 0.096
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

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Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); 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: WinGX (Farrugia, 1998).

2-Hydroxy-6-[(2-methoxyphenyl)aminomethylene]cyclohexa-2,4-dienone top
Crystal data top
C14H13NO3F(000) = 512
Mr = 243.25Dx = 1.412 Mg m3
Monoclinic, P21/nMelting point = 478–479 K
Hall symbol: -P2ynMo Kα radiation, λ = 0.71073 Å
a = 7.5517 (7) ÅCell parameters from 5462 reflections
b = 11.3022 (12) Åθ = 2.4–27.9°
c = 13.4646 (13) ŵ = 0.10 mm1
β = 95.186 (8)°T = 296 K
V = 1144.5 (2) Å3Prism, red
Z = 40.30 × 0.21 × 0.15 mm
Data collection top
Stoe IPDS-II
diffractometer
2724 independent reflections
Radiation source: fine-focus sealed tube1551 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
Detector resolution: 6.67 pixels mm-1θmax = 27.9°, θmin = 2.4°
rotation method scansh = 99
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 1414
Tmin = 0.973, Tmax = 0.993l = 1717
13408 measured reflections
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0515P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max < 0.001
2724 reflectionsΔρmax = 0.15 e Å3
166 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (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
C10.38091 (18)0.27402 (13)0.52307 (10)0.0359 (3)
C20.2084 (2)0.27024 (14)0.54917 (11)0.0430 (4)
H20.16930.32630.59280.052*
C30.0941 (2)0.18321 (15)0.51041 (13)0.0488 (4)
H30.02240.18070.52760.059*
C40.1526 (2)0.10037 (15)0.44651 (13)0.0510 (4)
H40.07480.04200.42070.061*
C50.3242 (2)0.10202 (15)0.41993 (13)0.0486 (4)
H50.36250.04480.37710.058*
C60.43909 (19)0.18959 (14)0.45761 (11)0.0400 (4)
C70.6681 (2)0.13436 (19)0.35528 (14)0.0615 (5)
H7A0.67190.05220.37360.092*
H7B0.78460.15970.34120.092*
H7C0.58660.14510.29700.092*
C80.4864 (2)0.44130 (13)0.62608 (11)0.0372 (3)
H80.37630.44830.65140.045*
C90.62320 (18)0.51849 (13)0.66199 (10)0.0350 (3)
C100.79323 (19)0.51154 (13)0.62430 (10)0.0359 (3)
C110.92898 (19)0.58763 (14)0.66900 (11)0.0394 (4)
C120.8943 (2)0.66410 (15)0.74234 (12)0.0460 (4)
H120.98530.71230.77050.055*
C130.7244 (2)0.67254 (15)0.77716 (12)0.0472 (4)
H130.70340.72630.82700.057*
C140.5917 (2)0.60150 (13)0.73724 (11)0.0422 (4)
H140.47900.60740.75950.051*
N10.50625 (15)0.36031 (11)0.55897 (9)0.0360 (3)
H10.60690.35930.53370.043*
O10.61099 (14)0.20249 (10)0.43513 (9)0.0527 (3)
O20.82672 (14)0.43948 (10)0.55379 (8)0.0456 (3)
O31.09670 (14)0.58140 (11)0.63867 (9)0.0529 (3)
H3A1.09090.56270.57960.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0364 (8)0.0356 (8)0.0356 (8)0.0036 (6)0.0031 (6)0.0029 (6)
C20.0443 (9)0.0439 (9)0.0420 (9)0.0039 (7)0.0103 (7)0.0027 (7)
C30.0411 (8)0.0538 (10)0.0528 (10)0.0105 (7)0.0114 (7)0.0003 (8)
C40.0499 (10)0.0481 (10)0.0558 (11)0.0152 (8)0.0083 (8)0.0055 (8)
C50.0496 (10)0.0421 (9)0.0548 (10)0.0051 (7)0.0087 (8)0.0085 (8)
C60.0364 (8)0.0420 (9)0.0422 (9)0.0014 (6)0.0071 (6)0.0014 (7)
C70.0525 (10)0.0724 (13)0.0617 (12)0.0044 (9)0.0166 (9)0.0171 (10)
C80.0380 (8)0.0391 (8)0.0352 (8)0.0016 (6)0.0069 (6)0.0033 (7)
C90.0385 (8)0.0350 (8)0.0319 (8)0.0006 (6)0.0051 (6)0.0019 (6)
C100.0398 (8)0.0353 (8)0.0328 (8)0.0008 (6)0.0054 (6)0.0002 (6)
C110.0380 (8)0.0436 (9)0.0368 (8)0.0028 (6)0.0056 (6)0.0003 (7)
C120.0490 (9)0.0474 (9)0.0415 (9)0.0107 (7)0.0042 (7)0.0057 (7)
C130.0591 (10)0.0434 (9)0.0400 (9)0.0032 (8)0.0104 (7)0.0098 (7)
C140.0466 (9)0.0408 (9)0.0407 (9)0.0010 (7)0.0120 (7)0.0017 (7)
N10.0336 (6)0.0379 (7)0.0372 (7)0.0015 (5)0.0058 (5)0.0000 (5)
O10.0412 (6)0.0614 (8)0.0573 (7)0.0051 (5)0.0134 (5)0.0183 (6)
O20.0426 (6)0.0496 (7)0.0460 (6)0.0033 (5)0.0126 (5)0.0123 (5)
O30.0389 (6)0.0702 (8)0.0504 (7)0.0083 (5)0.0078 (5)0.0123 (6)
Geometric parameters (Å, º) top
C1—C21.380 (2)C8—N11.3043 (19)
C1—C61.397 (2)C8—C91.404 (2)
C1—N11.4135 (18)C8—H80.9300
C2—C31.380 (2)C9—C141.417 (2)
C2—H20.9300C9—C101.425 (2)
C3—C41.372 (2)C10—O21.2931 (17)
C3—H30.9300C10—C111.429 (2)
C4—C51.375 (2)C11—C121.355 (2)
C4—H40.9300C11—O31.3673 (18)
C5—C61.382 (2)C12—C131.409 (2)
C5—H50.9300C12—H120.9300
C6—O11.3671 (18)C13—C141.357 (2)
C7—O11.421 (2)C13—H130.9300
C7—H7A0.9600C14—H140.9300
C7—H7B0.9600N1—H10.8600
C7—H7C0.9600O3—H3A0.8200
C2—C1—C6119.84 (14)N1—C8—H8118.4
C2—C1—N1123.54 (14)C9—C8—H8118.4
C6—C1—N1116.62 (13)C8—C9—C14119.46 (13)
C3—C2—C1119.90 (15)C8—C9—C10120.11 (13)
C3—C2—H2120.0C14—C9—C10120.41 (13)
C1—C2—H2120.0O2—C10—C9122.59 (13)
C4—C3—C2119.86 (15)O2—C10—C11120.52 (13)
C4—C3—H3120.1C9—C10—C11116.88 (13)
C2—C3—H3120.1C12—C11—O3119.70 (14)
C3—C4—C5121.24 (15)C12—C11—C10120.82 (14)
C3—C4—H4119.4O3—C11—C10119.47 (14)
C5—C4—H4119.4C11—C12—C13121.82 (15)
C4—C5—C6119.29 (16)C11—C12—H12119.1
C4—C5—H5120.4C13—C12—H12119.1
C6—C5—H5120.4C14—C13—C12119.38 (15)
O1—C6—C5124.90 (15)C14—C13—H13120.3
O1—C6—C1115.22 (13)C12—C13—H13120.3
C5—C6—C1119.87 (14)C13—C14—C9120.63 (15)
O1—C7—H7A109.5C13—C14—H14119.7
O1—C7—H7B109.5C9—C14—H14119.7
H7A—C7—H7B109.5C8—N1—C1127.29 (13)
O1—C7—H7C109.5C8—N1—H1116.4
H7A—C7—H7C109.5C1—N1—H1116.4
H7B—C7—H7C109.5C6—O1—C7117.98 (13)
N1—C8—C9123.20 (13)C11—O3—H3A109.5
C6—C1—C2—C30.1 (2)C14—C9—C10—C112.7 (2)
N1—C1—C2—C3179.73 (14)O2—C10—C11—C12179.42 (15)
C1—C2—C3—C40.4 (3)C9—C10—C11—C121.3 (2)
C2—C3—C4—C50.0 (3)O2—C10—C11—O31.9 (2)
C3—C4—C5—C60.7 (3)C9—C10—C11—O3177.35 (14)
C4—C5—C6—O1178.39 (16)O3—C11—C12—C13179.06 (15)
C4—C5—C6—C10.9 (3)C10—C11—C12—C130.4 (2)
C2—C1—C6—O1178.83 (14)C11—C12—C13—C140.7 (3)
N1—C1—C6—O11.0 (2)C12—C13—C14—C90.7 (2)
C2—C1—C6—C50.6 (2)C8—C9—C14—C13176.30 (15)
N1—C1—C6—C5179.61 (14)C10—C9—C14—C132.5 (2)
N1—C8—C9—C14178.05 (14)C9—C8—N1—C1175.57 (13)
N1—C8—C9—C100.7 (2)C2—C1—N1—C86.0 (2)
C8—C9—C10—O23.2 (2)C6—C1—N1—C8174.21 (14)
C14—C9—C10—O2178.06 (13)C5—C6—O1—C711.1 (2)
C8—C9—C10—C11176.04 (13)C1—C6—O1—C7168.29 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.861.892.5870 (16)137
O3—H3A···O2i0.821.952.7160 (16)154
C8—H8···O3ii0.932.593.3597 (19)141
Symmetry codes: (i) x+2, y+1, z+1; (ii) x1, y, z.
 

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