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The molecule of the title compound, C16H12N2O2, is nearly planar, and adopts the keto–amine tautomeric form with an intramolecular N—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/S1600536804002971/ob6347sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002971/ob6347Isup2.hkl
Contains datablock I

CCDC reference: 236071

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.071
  • Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 .. CG1 = 3.09 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. CG3 = 3.05 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. CG3 = 2.91 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 29.29 From the CIF: _reflns_number_total 1876 Count of symmetry unique reflns 1899 Completeness (_total/calc) 98.79% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 4 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-RED32 (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-[(3-Hydroxypyridin-2-ylamino)methylene]naphthalen-2(1H)-one top
Crystal data top
C16H12N2O2F(000) = 276
Mr = 264.28Dx = 1.381 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 14275 reflections
a = 8.8268 (14) Åθ = 1.7–29.3°
b = 5.9191 (6) ŵ = 0.09 mm1
c = 12.1670 (19) ÅT = 293 K
β = 90.277 (13)°Plate, orange
V = 635.68 (16) Å30.56 × 0.25 × 0.11 mm
Z = 2
Data collection top
Stoe IPDS-2
diffractometer
1876 independent reflections
Radiation source: fine-focus sealed tube1363 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 6.67 pixels mm-1θmax = 29.3°, θmin = 1.7°
ω scansh = 1212
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 78
Tmin = 0.964, Tmax = 0.991l = 1616
12064 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)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.071All H-atom parameters refined
S = 0.98 w = 1/[σ2(Fo2) + (0.0367P)2]
where P = (Fo2 + 2Fc2)/3
1876 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.09 e Å3
1 restraintΔρmin = 0.16 e Å3
Special details top

Experimental. 360 frames, detector distance = 100 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
C10.70290 (19)0.4453 (3)0.84288 (12)0.0360 (4)
C20.59578 (19)0.5976 (3)0.79294 (13)0.0405 (4)
C30.5541 (2)0.7970 (3)0.85241 (15)0.0445 (5)
C40.6106 (2)0.8392 (4)0.95305 (15)0.0437 (4)
C50.71156 (18)0.6868 (3)1.00805 (13)0.0381 (4)
C60.7609 (2)0.7300 (4)1.11674 (14)0.0470 (5)
C70.8521 (2)0.5810 (4)1.17054 (15)0.0507 (5)
C80.8986 (2)0.3845 (4)1.11824 (14)0.0475 (5)
C90.8526 (2)0.3384 (4)1.01211 (14)0.0424 (4)
C100.75802 (19)0.4877 (3)0.95451 (13)0.0352 (4)
C110.7551 (2)0.2594 (3)0.78381 (13)0.0372 (4)
C120.7620 (2)0.0313 (3)0.61839 (13)0.0390 (4)
C130.7028 (2)0.0146 (3)0.51179 (14)0.0429 (4)
C140.7443 (2)0.1712 (4)0.45064 (15)0.0521 (5)
C150.8429 (2)0.3252 (4)0.49607 (16)0.0560 (5)
C160.8977 (2)0.2922 (4)0.60120 (17)0.0514 (5)
N10.71290 (18)0.2141 (3)0.68162 (11)0.0414 (4)
N20.85790 (17)0.1145 (3)0.66277 (11)0.0451 (4)
O10.53901 (15)0.5584 (2)0.69821 (10)0.0534 (4)
O20.61023 (17)0.1825 (3)0.47848 (11)0.0605 (4)
H10.646 (2)0.316 (4)0.6534 (16)0.050 (6)*
H20.563 (3)0.136 (6)0.419 (2)0.107 (10)*
H30.481 (2)0.895 (4)0.8158 (15)0.049 (5)*
H40.582 (2)0.973 (4)0.9906 (16)0.056 (6)*
H60.722 (2)0.867 (4)1.1528 (16)0.055 (6)*
H70.884 (2)0.610 (4)1.2414 (17)0.054 (6)*
H80.966 (2)0.278 (4)1.1576 (16)0.052 (6)*
H90.890 (2)0.201 (4)0.9805 (14)0.046 (5)*
H110.823 (2)0.155 (4)0.8138 (14)0.040 (5)*
H140.700 (2)0.190 (4)0.3762 (16)0.052 (5)*
H150.872 (3)0.458 (4)0.4540 (18)0.061 (6)*
H160.972 (3)0.394 (5)0.637 (2)0.074 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0403 (9)0.0377 (10)0.0300 (8)0.0015 (7)0.0054 (7)0.0009 (7)
C20.0428 (10)0.0438 (11)0.0347 (8)0.0007 (9)0.0045 (7)0.0032 (8)
C30.0466 (10)0.0418 (12)0.0450 (9)0.0068 (9)0.0036 (8)0.0056 (8)
C40.0473 (10)0.0369 (11)0.0469 (9)0.0016 (8)0.0023 (8)0.0047 (9)
C50.0394 (9)0.0392 (10)0.0358 (8)0.0026 (8)0.0004 (6)0.0048 (8)
C60.0494 (11)0.0524 (12)0.0393 (9)0.0012 (10)0.0010 (8)0.0129 (9)
C70.0502 (11)0.0691 (15)0.0326 (9)0.0013 (10)0.0060 (7)0.0096 (9)
C80.0478 (11)0.0591 (13)0.0355 (8)0.0048 (10)0.0103 (7)0.0022 (9)
C90.0470 (10)0.0445 (11)0.0358 (8)0.0052 (9)0.0073 (7)0.0029 (8)
C100.0368 (9)0.0378 (10)0.0310 (7)0.0034 (7)0.0031 (6)0.0017 (7)
C110.0412 (9)0.0386 (10)0.0318 (8)0.0009 (8)0.0070 (7)0.0020 (7)
C120.0422 (9)0.0402 (10)0.0345 (8)0.0044 (8)0.0030 (7)0.0068 (7)
C130.0446 (10)0.0481 (11)0.0361 (9)0.0011 (9)0.0071 (7)0.0049 (8)
C140.0553 (11)0.0613 (13)0.0396 (9)0.0019 (11)0.0050 (8)0.0145 (10)
C150.0591 (13)0.0573 (14)0.0518 (11)0.0034 (12)0.0064 (9)0.0155 (11)
C160.0521 (11)0.0486 (13)0.0536 (10)0.0059 (10)0.0001 (9)0.0052 (10)
N10.0487 (9)0.0428 (9)0.0325 (6)0.0027 (8)0.0103 (6)0.0048 (7)
N20.0460 (9)0.0488 (10)0.0405 (8)0.0015 (8)0.0053 (6)0.0027 (7)
O10.0624 (8)0.0578 (9)0.0397 (7)0.0106 (7)0.0204 (6)0.0006 (6)
O20.0736 (10)0.0614 (10)0.0462 (7)0.0131 (8)0.0272 (7)0.0153 (7)
Geometric parameters (Å, º) top
C1—C111.394 (2)C9—C101.401 (2)
C1—C21.439 (2)C9—H90.96 (2)
C1—C101.462 (2)C11—N11.3237 (19)
C2—O11.276 (2)C11—H110.94 (2)
C2—C31.433 (3)C12—N21.322 (2)
C3—C41.343 (3)C12—N11.398 (2)
C3—H30.97 (2)C12—C131.399 (2)
C4—C51.432 (3)C13—O21.347 (2)
C4—H40.95 (2)C13—C141.379 (3)
C5—C101.409 (2)C14—C151.374 (3)
C5—C61.413 (2)C14—H140.99 (2)
C6—C71.360 (3)C15—C161.379 (3)
C6—H60.99 (2)C15—H150.97 (3)
C7—C81.389 (3)C16—N21.339 (3)
C7—H70.92 (2)C16—H161.00 (3)
C8—C91.379 (2)N1—H10.91 (2)
C8—H80.99 (2)O2—H20.88 (3)
C11—C1—C2119.67 (14)C9—C10—C5118.07 (15)
C11—C1—C10120.33 (15)C9—C10—C1123.44 (16)
C2—C1—C10119.99 (15)C5—C10—C1118.47 (15)
O1—C2—C3120.34 (16)N1—C11—C1123.50 (16)
O1—C2—C1121.47 (17)N1—C11—H11114.2 (11)
C3—C2—C1118.19 (15)C1—C11—H11122.3 (11)
C4—C3—C2121.23 (17)N2—C12—N1118.69 (14)
C4—C3—H3123.4 (12)N2—C12—C13124.60 (17)
C2—C3—H3115.4 (12)N1—C12—C13116.70 (16)
C3—C4—C5122.42 (19)O2—C13—C14126.04 (15)
C3—C4—H4119.6 (12)O2—C13—C12116.74 (17)
C5—C4—H4118.0 (12)C14—C13—C12117.22 (17)
C10—C5—C6119.65 (17)C15—C14—C13118.78 (17)
C10—C5—C4119.54 (15)C15—C14—H14122.6 (12)
C6—C5—C4120.78 (18)C13—C14—H14118.6 (12)
C7—C6—C5120.81 (19)C14—C15—C16119.8 (2)
C7—C6—H6121.7 (11)C14—C15—H15119.5 (14)
C5—C6—H6117.4 (11)C16—C15—H15120.7 (14)
C6—C7—C8119.86 (17)N2—C16—C15122.6 (2)
C6—C7—H7120.5 (14)N2—C16—H16113.8 (14)
C8—C7—H7119.6 (14)C15—C16—H16123.6 (15)
C9—C8—C7120.59 (18)C11—N1—C12125.96 (16)
C9—C8—H8120.1 (12)C11—N1—H1113.5 (13)
C7—C8—H8119.3 (12)C12—N1—H1120.6 (13)
C8—C9—C10121.02 (19)C12—N2—C16116.95 (15)
C8—C9—H9116.4 (11)C13—O2—H2108 (2)
C10—C9—H9122.6 (11)
C11—C1—C2—O14.9 (3)C11—C1—C10—C96.2 (3)
C10—C1—C2—O1175.94 (17)C2—C1—C10—C9174.67 (17)
C11—C1—C2—C3174.90 (16)C11—C1—C10—C5175.08 (15)
C10—C1—C2—C34.3 (2)C2—C1—C10—C54.1 (2)
O1—C2—C3—C4178.82 (19)C2—C1—C11—N10.9 (3)
C1—C2—C3—C41.4 (3)C10—C1—C11—N1178.28 (17)
C2—C3—C4—C51.7 (3)N2—C12—C13—O2177.82 (17)
C3—C4—C5—C101.9 (3)N1—C12—C13—O23.3 (2)
C3—C4—C5—C6175.9 (2)N2—C12—C13—C142.1 (3)
C10—C5—C6—C70.3 (3)N1—C12—C13—C14176.77 (17)
C4—C5—C6—C7177.47 (18)O2—C13—C14—C15178.5 (2)
C5—C6—C7—C80.4 (3)C12—C13—C14—C151.5 (3)
C6—C7—C8—C90.2 (3)C13—C14—C15—C160.3 (3)
C7—C8—C9—C100.1 (3)C14—C15—C16—N20.4 (3)
C8—C9—C10—C50.2 (3)C1—C11—N1—C12179.67 (17)
C8—C9—C10—C1178.55 (18)N2—C12—N1—C110.9 (3)
C6—C5—C10—C90.0 (2)C13—C12—N1—C11179.90 (18)
C4—C5—C10—C9177.80 (17)N1—C12—N2—C16177.45 (16)
C6—C5—C10—C1178.83 (17)C13—C12—N2—C161.4 (3)
C4—C5—C10—C11.0 (2)C15—C16—N2—C120.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.91 (2)1.80 (2)2.560 (2)139 (2)
O2—H2···O1i0.88 (3)1.74 (3)2.621 (2)176 (3)
C15—H15···Cg1ii0.97 (3)3.09 (3)3.719 (2)124 (2)
C4—H4···Cg2iii0.95 (2)2.68 (2)3.456 (2)140 (2)
C3—H3···Cg3iv0.97 (2)3.05 (2)3.625 (2)119 (1)
C9—H9···Cg3iv0.96 (2)2.91 (2)3.633 (2)133 (1)
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x, y1/2, z+1; (iii) x+1, y+1/2, z; (iv) x, y1/2, z.
 

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