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The title Schiff base compound, C14H14N2O2, displays an E configuration with respect to the C=N double bond. The dihedral angle between the benzene and pyridine rings is 5.4 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048350/sg2194sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048350/sg2194Isup2.hkl
Contains datablock I

CCDC reference: 667300

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.060
  • wR factor = 0.159
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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 0 ALERT type 5 Informative message, check

Comment top

The compounds derived from the condensation reaction of aromatic carbaldehydes with hydrazides exhibit a wide range of biological activities and applications (Tarafder et al., 2002; Cukurovali et al., 2002; Ali et al., 2002). Recently, the author has reported a Schiff base compound (Li, 2007). As a further investigation, the author reports here the crystal structure of the new Schiff base compound, Fig. 1.

All the bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable with those observed in similar compounds (Qiu et al., 2006; Yang and Guo, 2006; Yang, 2006). The C8N1 bond length of 1.285 (3) Å conforms to the value for a double bond, and is comparable with that in other Schiff bases (Qian et al., 2006; Zhao, 2006). The molecule displays an E configuration about the CN double bond. The dihedral angle between the benzene ring and the pyridine ring is 5.4 (2)°.

The molecular structure is stablized by weak πi-πi interactions, stacking along the b axis (Fig. 2).

Related literature top

For related literature, see: Ali et al. (2002); Allen et al. (1987); Cukurovali et al. (2002); Li (2007); Qian et al. (2006); Qiu et al. (2006); Tarafder et al. (2002); Yang (2006); Yang & Guo (2006); Zhao (2006).

Experimental top

3-Methoxysalicylaldehyde (0.1 mmol, 15.2 mg) and 4-methylpyridin-2-ylamine (0.1 mmol, 10.8 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution. Crystals of (I) were formed by gradual evaporation of the solvent over a week at room temperature (yield 87.2%).

Refinement top

H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms, with O—H = 0.82 Å, C—H = 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl,O).

Structure description top

The compounds derived from the condensation reaction of aromatic carbaldehydes with hydrazides exhibit a wide range of biological activities and applications (Tarafder et al., 2002; Cukurovali et al., 2002; Ali et al., 2002). Recently, the author has reported a Schiff base compound (Li, 2007). As a further investigation, the author reports here the crystal structure of the new Schiff base compound, Fig. 1.

All the bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable with those observed in similar compounds (Qiu et al., 2006; Yang and Guo, 2006; Yang, 2006). The C8N1 bond length of 1.285 (3) Å conforms to the value for a double bond, and is comparable with that in other Schiff bases (Qian et al., 2006; Zhao, 2006). The molecule displays an E configuration about the CN double bond. The dihedral angle between the benzene ring and the pyridine ring is 5.4 (2)°.

The molecular structure is stablized by weak πi-πi interactions, stacking along the b axis (Fig. 2).

For related literature, see: Ali et al. (2002); Allen et al. (1987); Cukurovali et al. (2002); Li (2007); Qian et al. (2006); Qiu et al. (2006); Tarafder et al. (2002); Yang (2006); Yang & Guo (2006); Zhao (2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. Intramolecular hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the b axis.
2-Methoxy-6-[(4-methylpyridin-2-ylimino)methyl]phenol top
Crystal data top
C14H14N2O2F(000) = 512
Mr = 242.27Dx = 1.333 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 713 reflections
a = 9.997 (2) Åθ = 2.5–24.5°
b = 4.896 (1) ŵ = 0.09 mm1
c = 24.729 (5) ÅT = 298 K
β = 94.24 (3)°Block, yellow
V = 1207.1 (4) Å30.23 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2498 independent reflections
Radiation source: fine-focus sealed tube1384 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ω scansθmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.979, Tmax = 0.982k = 66
8333 measured reflectionsl = 3031
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)] = 0.060H-atom parameters constrained
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0322P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2498 reflectionsΔρmax = 0.18 e Å3
167 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (3)
Crystal data top
C14H14N2O2V = 1207.1 (4) Å3
Mr = 242.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.997 (2) ŵ = 0.09 mm1
b = 4.896 (1) ÅT = 298 K
c = 24.729 (5) Å0.23 × 0.20 × 0.20 mm
β = 94.24 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2498 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1384 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.982Rint = 0.060
8333 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 1.03Δρmax = 0.18 e Å3
2498 reflectionsΔρmin = 0.18 e Å3
167 parameters
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
O10.25493 (18)0.8248 (4)0.07335 (7)0.0551 (6)
H10.19720.93830.07890.083*
O20.44898 (18)0.4723 (4)0.07002 (7)0.0585 (6)
N10.08363 (19)1.0839 (4)0.12784 (8)0.0442 (5)
N20.0684 (2)1.3400 (4)0.17759 (8)0.0516 (6)
C10.2269 (2)0.7364 (5)0.16759 (10)0.0407 (6)
C20.2902 (2)0.6903 (5)0.11964 (10)0.0403 (6)
C30.3939 (2)0.4971 (5)0.11899 (10)0.0438 (6)
C40.4341 (2)0.3547 (5)0.16547 (11)0.0491 (7)
H40.50370.22880.16510.059*
C50.3704 (3)0.3993 (5)0.21317 (11)0.0507 (7)
H50.39740.30220.24440.061*
C60.2682 (3)0.5856 (5)0.21406 (10)0.0477 (7)
H60.22590.61240.24590.057*
C70.5342 (3)0.2432 (5)0.06291 (11)0.0584 (8)
H7A0.61010.25140.08900.088*
H7B0.56450.24630.02700.088*
H7C0.48520.07750.06800.088*
C80.1211 (2)0.9378 (5)0.16942 (10)0.0425 (6)
H80.07930.96190.20140.051*
C90.0183 (2)1.2843 (5)0.13012 (10)0.0412 (6)
C100.0592 (2)1.4159 (5)0.08256 (10)0.0461 (7)
H100.01991.37100.05080.055*
C110.1581 (2)1.6146 (5)0.08139 (10)0.0457 (7)
C120.2092 (2)1.6755 (5)0.13031 (11)0.0499 (7)
H120.27471.80930.13220.060*
C130.1623 (3)1.5363 (6)0.17616 (11)0.0573 (8)
H130.19831.58160.20860.069*
C140.2051 (3)1.7581 (7)0.02971 (12)0.0704 (9)
H14A0.29171.83740.03350.106*
H14B0.21121.62910.00040.106*
H14C0.14251.89930.02220.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0617 (13)0.0558 (13)0.0489 (11)0.0195 (9)0.0112 (9)0.0103 (9)
O20.0626 (12)0.0599 (13)0.0553 (12)0.0237 (9)0.0197 (9)0.0067 (10)
N10.0431 (12)0.0400 (13)0.0496 (13)0.0046 (10)0.0053 (10)0.0023 (11)
N20.0548 (14)0.0528 (15)0.0484 (14)0.0104 (11)0.0119 (11)0.0016 (11)
C10.0368 (14)0.0387 (15)0.0464 (15)0.0021 (11)0.0034 (11)0.0036 (12)
C20.0432 (14)0.0378 (14)0.0398 (15)0.0001 (11)0.0029 (11)0.0051 (12)
C30.0429 (14)0.0427 (15)0.0466 (16)0.0021 (12)0.0086 (12)0.0010 (13)
C40.0410 (15)0.0468 (17)0.0596 (18)0.0061 (12)0.0054 (13)0.0024 (14)
C50.0584 (17)0.0435 (16)0.0495 (17)0.0023 (13)0.0004 (13)0.0086 (13)
C60.0543 (17)0.0463 (16)0.0431 (15)0.0034 (13)0.0080 (12)0.0010 (13)
C70.0523 (16)0.0560 (19)0.069 (2)0.0111 (14)0.0191 (14)0.0042 (15)
C80.0429 (15)0.0392 (15)0.0460 (15)0.0031 (12)0.0077 (12)0.0049 (12)
C90.0391 (14)0.0365 (15)0.0486 (16)0.0014 (11)0.0072 (12)0.0047 (12)
C100.0470 (16)0.0480 (17)0.0442 (16)0.0034 (12)0.0102 (12)0.0052 (13)
C110.0437 (15)0.0463 (16)0.0472 (16)0.0036 (12)0.0030 (12)0.0024 (13)
C120.0458 (15)0.0444 (16)0.0601 (18)0.0102 (12)0.0082 (13)0.0010 (14)
C130.0637 (18)0.0569 (19)0.0536 (18)0.0143 (15)0.0205 (14)0.0019 (15)
C140.078 (2)0.075 (2)0.058 (2)0.0247 (17)0.0031 (15)0.0046 (16)
Geometric parameters (Å, º) top
O1—C21.345 (3)C6—H60.9300
O1—H10.8200C7—H7A0.9600
O2—C31.372 (3)C7—H7B0.9600
O2—C71.427 (3)C7—H7C0.9600
N1—C81.285 (3)C8—H80.9300
N1—C91.419 (3)C9—C101.376 (3)
N2—C91.338 (3)C10—C111.386 (3)
N2—C131.342 (3)C10—H100.9300
C1—C61.402 (3)C11—C121.380 (3)
C1—C21.403 (3)C11—C141.503 (4)
C1—C81.449 (3)C12—C131.375 (3)
C2—C31.404 (3)C12—H120.9300
C3—C41.379 (3)C13—H130.9300
C4—C51.399 (3)C14—H14A0.9600
C4—H40.9300C14—H14B0.9600
C5—C61.370 (3)C14—H14C0.9600
C5—H50.9300
C2—O1—H1109.5H7A—C7—H7C109.5
C3—O2—C7117.4 (2)H7B—C7—H7C109.5
C8—N1—C9121.4 (2)N1—C8—C1121.6 (2)
C9—N2—C13115.4 (2)N1—C8—H8119.2
C6—C1—C2118.9 (2)C1—C8—H8119.2
C6—C1—C8120.3 (2)N2—C9—C10123.2 (2)
C2—C1—C8120.8 (2)N2—C9—N1119.5 (2)
O1—C2—C1122.3 (2)C10—C9—N1117.3 (2)
O1—C2—C3117.9 (2)C9—C10—C11120.9 (2)
C1—C2—C3119.9 (2)C9—C10—H10119.6
O2—C3—C4125.4 (2)C11—C10—H10119.6
O2—C3—C2114.5 (2)C12—C11—C10116.3 (2)
C4—C3—C2120.1 (2)C12—C11—C14122.1 (2)
C3—C4—C5120.0 (2)C10—C11—C14121.6 (2)
C3—C4—H4120.0C13—C12—C11119.4 (2)
C5—C4—H4120.0C13—C12—H12120.3
C6—C5—C4120.3 (2)C11—C12—H12120.3
C6—C5—H5119.9N2—C13—C12124.9 (2)
C4—C5—H5119.9N2—C13—H13117.6
C5—C6—C1120.8 (2)C12—C13—H13117.6
C5—C6—H6119.6C11—C14—H14A109.5
C1—C6—H6119.6C11—C14—H14B109.5
O2—C7—H7A109.5H14A—C14—H14B109.5
O2—C7—H7B109.5C11—C14—H14C109.5
H7A—C7—H7B109.5H14A—C14—H14C109.5
O2—C7—H7C109.5H14B—C14—H14C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.588 (2)147

Experimental details

Crystal data
Chemical formulaC14H14N2O2
Mr242.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.997 (2), 4.896 (1), 24.729 (5)
β (°) 94.24 (3)
V3)1207.1 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.23 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.979, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
8333, 2498, 1384
Rint0.060
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.159, 1.03
No. of reflections2498
No. of parameters167
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.588 (2)147.0
 

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