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The title compound, C14H12N2O2, is stabilized in the solid state as an enol–imine tautomer, with a strong intra­molecular O—H...N hydrogen bond, one C—H...N and three C—H...O inter­molecular hydrogen bonds, generating edge-fused [S(6)R22(8)R22(8)R21(6)] motifs. The mol­ecule is approximately planar, with a dihedral angle of 4.40 (10)° between the two aromatic rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012913/at2241sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012913/at2241Isup2.hkl
Contains datablock I

CCDC reference: 643632

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.114
  • Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.100 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.22 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C8 PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O2 .. 2.79 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. O1 .. 2.71 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O2 .. 2.77 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. N2 .. 2.73 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 26.00 From the CIF: _reflns_number_total 1184 Count of symmetry unique reflns 1194 Completeness (_total/calc) 99.16% 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 8 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 3 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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, 1990); 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, 1999).

(E)-2-Hydroxy-5-methyl-3-[(2-pyridylimino)methyl]benzaldehyde top
Crystal data top
C14H12N2O2F(000) = 252
Mr = 240.26Dx = 1.315 Mg m3
Monoclinic, PcMelting point = 393–395 K
Hall symbol: P -2ycMo Kα radiation, λ = 0.71073 Å
a = 7.4049 (8) ÅCell parameters from 10246 reflections
b = 4.2957 (3) Åθ = 2.1–28.0°
c = 20.154 (2) ŵ = 0.09 mm1
β = 108.847 (8)°T = 296 K
V = 606.72 (10) Å3Prismatic rod, red
Z = 20.56 × 0.27 × 0.18 mm
Data collection top
Stoe IPDSII
diffractometer
1184 independent reflections
Radiation source: fine-focus sealed tube853 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.100
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.9°
ω scansh = 99
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 55
Tmin = 0.954, Tmax = 0.989l = 2424
10246 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)] = 0.043H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.07P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
1184 reflectionsΔρmax = 0.18 e Å3
164 parametersΔρmin = 0.16 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.064 (13)
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
C10.1508 (4)0.9603 (7)0.77188 (17)0.0589 (8)
C20.3194 (4)1.0599 (7)0.75990 (17)0.0608 (8)
C30.4422 (4)1.2641 (8)0.80672 (17)0.0634 (9)
C40.3982 (4)1.3660 (7)0.86578 (19)0.0626 (8)
H40.48121.50230.89690.075*
C50.2348 (4)1.2696 (7)0.87913 (18)0.0620 (8)
C60.1144 (4)1.0688 (8)0.83129 (16)0.0626 (8)
H60.00351.00320.83930.075*
C70.6152 (5)1.3830 (9)0.7946 (2)0.0773 (10)
H70.63981.31660.75450.093*
C80.1889 (6)1.3835 (9)0.9425 (2)0.0783 (10)
H8A0.07091.29290.94300.117*
H8B0.17721.60620.94070.117*
H8C0.28941.32410.98420.117*
C90.0206 (4)0.7485 (8)0.72540 (18)0.0621 (7)
H90.08830.68720.73540.075*
C100.0854 (5)0.4396 (7)0.62400 (18)0.0630 (8)
C110.0538 (5)0.3529 (8)0.5637 (2)0.0758 (10)
H110.05480.41960.55430.091*
C120.1847 (6)0.1655 (9)0.5171 (2)0.0847 (11)
H120.16680.10450.47540.102*
C130.3424 (6)0.0696 (9)0.5330 (2)0.0841 (11)
H130.43440.05580.50230.101*
C140.3604 (6)0.1640 (9)0.5955 (2)0.0844 (11)
H140.46600.09520.60670.101*
N10.0498 (4)0.6410 (7)0.67039 (15)0.0644 (7)
N20.2356 (4)0.3489 (6)0.64126 (16)0.0738 (8)
O10.3616 (3)0.9620 (6)0.70300 (13)0.0784 (7)
H10.27780.84370.68000.118*
O20.7275 (3)1.5603 (7)0.83302 (16)0.0938 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0536 (15)0.0612 (17)0.067 (2)0.0012 (14)0.0261 (14)0.0092 (14)
C20.0576 (17)0.0658 (17)0.066 (2)0.0020 (14)0.0294 (15)0.0045 (16)
C30.0534 (17)0.0697 (19)0.071 (2)0.0004 (15)0.0254 (15)0.0047 (16)
C40.0553 (15)0.0678 (17)0.068 (2)0.0011 (14)0.0241 (14)0.0014 (15)
C50.0633 (17)0.0651 (17)0.063 (2)0.0049 (15)0.0275 (14)0.0046 (15)
C60.0587 (17)0.0637 (17)0.073 (2)0.0013 (13)0.0315 (16)0.0071 (15)
C70.0610 (18)0.092 (2)0.087 (3)0.0077 (18)0.0338 (17)0.005 (2)
C80.079 (2)0.090 (2)0.078 (3)0.0017 (19)0.0414 (18)0.0062 (19)
C90.0585 (15)0.0606 (16)0.073 (2)0.0017 (13)0.0295 (15)0.0069 (14)
C100.0683 (19)0.0601 (16)0.065 (2)0.0005 (15)0.0270 (16)0.0062 (16)
C110.080 (2)0.081 (2)0.073 (3)0.0025 (18)0.034 (2)0.0016 (19)
C120.098 (3)0.088 (2)0.071 (3)0.002 (2)0.032 (2)0.006 (2)
C130.082 (3)0.082 (2)0.084 (3)0.005 (2)0.021 (2)0.005 (2)
C140.076 (2)0.095 (3)0.085 (3)0.014 (2)0.031 (2)0.008 (2)
N10.0641 (15)0.0667 (15)0.0682 (18)0.0001 (12)0.0294 (13)0.0051 (12)
N20.0677 (16)0.0828 (19)0.076 (2)0.0131 (14)0.0295 (14)0.0041 (15)
O10.0751 (14)0.0919 (17)0.0825 (18)0.0128 (13)0.0454 (13)0.0128 (13)
O20.0633 (14)0.119 (2)0.104 (2)0.0251 (15)0.0328 (13)0.0187 (18)
Geometric parameters (Å, º) top
C1—C61.390 (4)C8—H8C0.9600
C1—C21.412 (4)C9—N11.282 (4)
C1—C91.432 (5)C9—H90.9300
C2—O11.349 (4)C10—N21.326 (4)
C2—C31.390 (4)C10—C111.362 (5)
C3—C41.402 (4)C10—N11.422 (4)
C3—C71.471 (4)C11—C121.372 (5)
C4—C51.385 (4)C11—H110.9300
C4—H40.9300C12—C131.370 (6)
C5—C61.383 (5)C12—H120.9300
C5—C81.506 (5)C13—C141.369 (6)
C6—H60.9300C13—H130.9300
C7—O21.206 (4)C14—N21.336 (5)
C7—H70.9300C14—H140.9300
C8—H8A0.9600O1—H10.8200
C8—H8B0.9600
C6—C1—C2118.3 (3)C5—C8—H8C109.5
C6—C1—C9119.9 (3)H8A—C8—H8C109.5
C2—C1—C9121.8 (3)H8B—C8—H8C109.5
O1—C2—C3119.6 (3)N1—C9—C1121.9 (3)
O1—C2—C1120.7 (3)N1—C9—H9119.1
C3—C2—C1119.7 (3)C1—C9—H9119.1
C2—C3—C4119.6 (3)N2—C10—C11123.7 (3)
C2—C3—C7121.4 (3)N2—C10—N1118.6 (3)
C4—C3—C7119.1 (3)C11—C10—N1117.8 (3)
C5—C4—C3121.9 (3)C10—C11—C12119.0 (3)
C5—C4—H4119.0C10—C11—H11120.5
C3—C4—H4119.0C12—C11—H11120.5
C6—C5—C4117.3 (3)C13—C12—C11118.9 (4)
C6—C5—C8121.5 (3)C13—C12—H12120.5
C4—C5—C8121.2 (3)C11—C12—H12120.5
C5—C6—C1123.3 (3)C14—C13—C12118.0 (4)
C5—C6—H6118.4C14—C13—H13121.0
C1—C6—H6118.4C12—C13—H13121.0
O2—C7—C3124.8 (4)N2—C14—C13124.1 (4)
O2—C7—H7117.6N2—C14—H14118.0
C3—C7—H7117.6C13—C14—H14118.0
C5—C8—H8A109.5C9—N1—C10120.5 (3)
C5—C8—H8B109.5C10—N2—C14116.4 (3)
H8A—C8—H8B109.5C2—O1—H1109.5
C6—C1—C2—O1179.9 (3)C2—C3—C7—O2180.0 (3)
C9—C1—C2—O11.2 (4)C4—C3—C7—O21.7 (6)
C6—C1—C2—C30.7 (4)C6—C1—C9—N1179.4 (3)
C9—C1—C2—C3179.6 (3)C2—C1—C9—N10.6 (5)
O1—C2—C3—C4179.9 (3)N2—C10—C11—C121.1 (5)
C1—C2—C3—C40.7 (5)N1—C10—C11—C12178.3 (3)
O1—C2—C3—C71.6 (5)C10—C11—C12—C130.5 (5)
C1—C2—C3—C7177.6 (3)C11—C12—C13—C140.6 (6)
C2—C3—C4—C50.1 (5)C12—C13—C14—N21.4 (6)
C7—C3—C4—C5178.2 (3)C1—C9—N1—C10177.8 (3)
C3—C4—C5—C60.5 (4)N2—C10—N1—C94.5 (4)
C3—C4—C5—C8179.5 (3)C11—C10—N1—C9174.9 (3)
C4—C5—C6—C10.5 (5)C11—C10—N2—C140.5 (5)
C8—C5—C6—C1179.5 (3)N1—C10—N2—C14178.9 (3)
C2—C1—C6—C50.1 (4)C13—C14—N2—C100.8 (6)
C9—C1—C6—C5179.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.852.585 (3)148
C9—H9···O2i0.932.793.620 (4)150
C14—H14···O1i0.932.713.546 (5)151
C6—H6···O2i0.932.773.612 (4)152
C7—H7···N2ii0.932.733.606 (5)158
Symmetry codes: (i) x1, y1, z; (ii) x+1, y+1, z.
 

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