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The molecule of the title compound, C18H15NO2, is not completely planar. It adopts a keto–amine tautomeric form with an intramolecular N—H...O and an intermolecular O—H...O hydrogen bond. The mol­ecules are linked by O—H...O hydrogen bonds into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008827/fl6094sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008827/fl6094Isup2.hkl
Contains datablock I

CCDC reference: 239268

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.121
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

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).

1-[(2-Hydroxy-5-methylphenylamino)methylene]naphthalen-2(1H)-one top
Crystal data top
C18H15NO2Z = 2
Mr = 277.31F(000) = 292
Triclinic, P1Dx = 1.348 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.126 (1) ÅCell parameters from 4617 reflections
b = 7.898 (1) Åθ = 2.9–27.8°
c = 13.684 (2) ŵ = 0.09 mm1
α = 77.698 (9)°T = 293 K
β = 85.43 (1)°Plate, orange
γ = 65.210 (9)°0.31 × 0.21 × 0.08 mm
V = 683.1 (2) Å3
Data collection top
Stoe IPDS-2
diffractometer
3240 independent reflections
Radiation source: fine-focus sealed tube1689 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.058
Detector resolution: 6.67 pixels mm-1θmax = 27.8°, θmin = 2.9°
ω scansh = 99
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 109
Tmin = 0.978, Tmax = 0.994l = 1717
11817 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0587P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max < 0.001
3240 reflectionsΔρmax = 0.18 e Å3
199 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (2)
Special details top

Experimental. 360 frames, detector distance = 80 mm

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
C10.7555 (3)0.5552 (3)0.62029 (13)0.0353 (4)
C20.7322 (3)0.4025 (2)0.59020 (14)0.0370 (4)
C30.6906 (3)0.2671 (3)0.66674 (15)0.0465 (5)
H30.67070.16870.64880.056*
C40.6798 (3)0.2795 (3)0.76336 (15)0.0479 (5)
H40.64910.19060.81020.057*
C50.7135 (3)0.4235 (3)0.79736 (14)0.0419 (5)
C60.7076 (4)0.4298 (3)0.89913 (15)0.0546 (6)
H60.67720.34040.94560.066*
C70.7456 (4)0.5642 (4)0.93147 (16)0.0607 (6)
H70.74010.56740.99920.073*
C80.7927 (4)0.6968 (3)0.86174 (15)0.0573 (6)
H80.82240.78690.88340.069*
C90.7958 (3)0.6962 (3)0.76210 (15)0.0479 (5)
H90.82550.78770.71700.058*
C100.7554 (3)0.5608 (3)0.72555 (14)0.0368 (4)
C110.7671 (3)0.7057 (3)0.54783 (14)0.0374 (5)
H110.77880.80470.56960.045*
C120.7620 (3)0.8618 (2)0.37156 (13)0.0344 (4)
C130.7663 (3)0.8286 (3)0.27549 (14)0.0388 (5)
H130.76920.71330.26780.047*
C140.7664 (3)0.9606 (3)0.19092 (14)0.0425 (5)
C150.7647 (3)1.1297 (3)0.20535 (16)0.0475 (5)
H150.76661.22070.15000.057*
C160.7602 (3)1.1661 (3)0.29962 (15)0.0446 (5)
H160.75871.28120.30660.054*
C170.7578 (3)1.0352 (3)0.38427 (14)0.0375 (4)
C180.7640 (4)0.9220 (4)0.08829 (15)0.0632 (7)
H18A0.76541.02790.03890.095*
H18B0.64140.90440.07980.095*
H18C0.88370.80910.08060.095*
N10.7624 (3)0.7150 (2)0.45154 (11)0.0365 (4)
O10.7465 (2)0.38604 (18)0.49846 (10)0.0444 (4)
O20.7473 (3)1.06858 (19)0.47751 (10)0.0497 (4)
H10.766 (3)0.601 (3)0.4388 (15)0.058 (6)*
H20.739 (5)1.188 (5)0.478 (2)0.110 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0417 (11)0.0307 (9)0.0360 (10)0.0182 (9)0.0009 (8)0.0046 (8)
C20.0431 (11)0.0311 (10)0.0398 (11)0.0188 (9)0.0001 (8)0.0055 (8)
C30.0634 (14)0.0366 (11)0.0501 (12)0.0318 (10)0.0012 (10)0.0070 (9)
C40.0613 (14)0.0413 (11)0.0466 (12)0.0309 (11)0.0032 (10)0.0004 (9)
C50.0481 (12)0.0386 (11)0.0393 (11)0.0200 (10)0.0004 (9)0.0042 (9)
C60.0700 (16)0.0540 (14)0.0395 (11)0.0292 (13)0.0030 (11)0.0018 (10)
C70.0817 (18)0.0664 (15)0.0359 (12)0.0317 (14)0.0032 (11)0.0126 (11)
C80.0798 (17)0.0585 (14)0.0451 (12)0.0360 (13)0.0019 (11)0.0173 (11)
C90.0657 (14)0.0431 (11)0.0431 (12)0.0295 (11)0.0005 (10)0.0103 (10)
C100.0409 (11)0.0313 (10)0.0382 (10)0.0152 (9)0.0004 (9)0.0065 (8)
C110.0482 (12)0.0307 (10)0.0394 (11)0.0210 (9)0.0013 (9)0.0096 (8)
C120.0423 (11)0.0298 (9)0.0342 (10)0.0187 (9)0.0014 (8)0.0050 (8)
C130.0465 (12)0.0336 (10)0.0408 (11)0.0197 (9)0.0009 (9)0.0089 (9)
C140.0468 (12)0.0442 (11)0.0353 (10)0.0184 (10)0.0009 (9)0.0059 (9)
C150.0597 (14)0.0394 (11)0.0399 (11)0.0227 (10)0.0010 (10)0.0037 (9)
C160.0557 (13)0.0302 (10)0.0507 (12)0.0226 (9)0.0002 (10)0.0035 (9)
C170.0429 (11)0.0337 (10)0.0386 (10)0.0182 (9)0.0004 (9)0.0080 (8)
C180.0857 (18)0.0646 (15)0.0387 (12)0.0305 (14)0.0023 (12)0.0088 (11)
N10.0497 (10)0.0293 (8)0.0358 (9)0.0211 (8)0.0026 (7)0.0078 (7)
O10.0685 (10)0.0342 (7)0.0405 (8)0.0298 (7)0.0020 (7)0.0098 (6)
O20.0843 (12)0.0353 (8)0.0407 (8)0.0346 (8)0.0023 (7)0.0096 (7)
Geometric parameters (Å, º) top
C1—C111.404 (2)C11—N11.306 (2)
C1—C21.429 (2)C11—H110.9300
C1—C101.450 (2)C12—C131.390 (3)
C2—O11.281 (2)C12—C171.404 (2)
C2—C31.438 (2)C12—N11.414 (2)
C3—C41.340 (3)C13—C141.383 (2)
C3—H30.9300C13—H130.9300
C4—C51.428 (3)C14—C151.386 (3)
C4—H40.9300C14—C181.502 (3)
C5—C61.401 (3)C15—C161.375 (3)
C5—C101.414 (2)C15—H150.9300
C6—C71.363 (3)C16—C171.383 (3)
C6—H60.9300C16—H160.9300
C7—C81.392 (3)C17—O21.347 (2)
C7—H70.9300C18—H18A0.9600
C8—C91.363 (3)C18—H18B0.9600
C8—H80.9300C18—H18C0.9600
C9—C101.410 (2)N1—H10.94 (2)
C9—H90.9300O2—H20.92 (3)
C11—C1—C2120.0 (2)N1—C11—H11118.1
C11—C1—C10119.7 (2)C1—C11—H11118.1
C2—C1—C10120.2 (2)C13—C12—C17119.38 (17)
O1—C2—C1121.7 (2)C13—C12—N1116.7 (2)
O1—C2—C3120.7 (2)C17—C12—N1123.91 (16)
C1—C2—C3117.6 (2)C14—C13—C12122.45 (17)
C4—C3—C2121.57 (17)C14—C13—H13118.8
C4—C3—H3119.2C12—C13—H13118.8
C2—C3—H3119.2C13—C14—C15117.13 (18)
C3—C4—C5122.66 (18)C13—C14—C18120.86 (19)
C3—C4—H4118.7C15—C14—C18122.00 (19)
C5—C4—H4118.7C16—C15—C14121.53 (19)
C6—C5—C10120.04 (18)C16—C15—H15119.2
C6—C5—C4121.56 (19)C14—C15—H15119.2
C10—C5—C4118.40 (17)C15—C16—C17121.45 (18)
C7—C6—C5121.4 (2)C15—C16—H16119.3
C7—C6—H6119.3C17—C16—H16119.3
C5—C6—H6119.3O2—C17—C16122.95 (16)
C6—C7—C8119.10 (19)O2—C17—C12118.98 (16)
C6—C7—H7120.5C16—C17—C12118.05 (17)
C8—C7—H7120.5C14—C18—H18A109.5
C9—C8—C7120.8 (2)C14—C18—H18B109.5
C9—C8—H8119.6H18A—C18—H18B109.5
C7—C8—H8119.6C14—C18—H18C109.5
C8—C9—C10121.80 (19)H18A—C18—H18C109.5
C8—C9—H9119.1H18B—C18—H18C109.5
C10—C9—H9119.1C11—N1—C12129.3 (2)
C9—C10—C5116.84 (17)C11—N1—H1110.2 (13)
C9—C10—C1123.81 (17)C12—N1—H1120.4 (13)
C5—C10—C1119.3 (2)C17—O2—H2112.4 (19)
N1—C11—C1123.8 (2)
C11—C1—C2—O18.6 (3)C2—C1—C10—C9174.09 (19)
C10—C1—C2—O1174.93 (19)C11—C1—C10—C5170.81 (19)
C11—C1—C2—C3170.99 (18)C2—C1—C10—C55.6 (3)
C10—C1—C2—C35.4 (3)C2—C1—C11—N11.6 (3)
O1—C2—C3—C4178.5 (2)C10—C1—C11—N1178.0 (2)
C1—C2—C3—C41.9 (3)C17—C12—C13—C140.1 (3)
C2—C3—C4—C51.6 (3)N1—C12—C13—C14179.98 (18)
C3—C4—C5—C6178.0 (2)C12—C13—C14—C150.8 (3)
C3—C4—C5—C101.4 (3)C12—C13—C14—C18178.0 (2)
C10—C5—C6—C71.3 (3)C13—C14—C15—C160.9 (3)
C4—C5—C6—C7178.1 (2)C18—C14—C15—C16177.9 (2)
C5—C6—C7—C80.5 (4)C14—C15—C16—C170.2 (3)
C6—C7—C8—C91.7 (4)C15—C16—C17—O2178.0 (2)
C7—C8—C9—C101.1 (4)C15—C16—C17—C120.6 (3)
C8—C9—C10—C50.7 (3)C13—C12—C17—O2177.96 (19)
C8—C9—C10—C1179.6 (2)N1—C12—C17—O22.1 (3)
C6—C5—C10—C91.8 (3)C13—C12—C17—C160.6 (3)
C4—C5—C10—C9177.57 (19)N1—C12—C17—C16179.33 (18)
C6—C5—C10—C1178.4 (2)C1—C11—N1—C12176.4 (2)
C4—C5—C10—C12.2 (3)C13—C12—N1—C11177.0 (2)
C11—C1—C10—C99.5 (3)C17—C12—N1—C112.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.94 (2)1.78 (2)2.588 (2)142 (2)
O2—H2···O1i0.92 (3)1.67 (3)2.581 (2)170 (3)
Symmetry code: (i) x, y+1, z.
 

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