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In the title compound, C13H10N2O2, the dihedral angle between the aromatic ring planes is 1.3 (2)°. The mol­ecules are linked into chains by inter­molecular C—H...O and O—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055754/hb2632sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055754/hb2632Isup2.hkl
Contains datablock I

CCDC reference: 672859

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.062
  • wR factor = 0.140
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.34 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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

Schiff bases are important intermediates in the preparation of many substances such as dyes, liquid crystals and corrosion inhibitors (e.g. Lindoy et al., 1976). We report here the synthesis and crystal structure of the title compound, (I), (Fig. 1), a new Schiff base.

This compound contains two aromatic rings linked through a imino group. An E configuration with respect to the CN bond is shown by the molecule, with a C—NC—C torsoin angle of -179.9 (3) °. The molecule of (I) is almost planr, with a dihedral angle of 1.3 (2)° between the benzene and pyridine rings.

As seen in Fig. 2, the molecules are linked into chains propagating in [100] by intermolecular C—H···O and O—H···N hydrogen bonds (Table 1). Thus, classical carboxylic acid inversion dimers do not feature in the packing.

Related literature top

For general background, see: Lindoy et al. (1976).

Experimental top

Pyridine-2-carboxaldehyde (5 mmol, 535.6 mg) in absolute ethanol (5 ml) was added dropwise to a absolute ethanol solution (15 ml) of m-aminobenzoic acid (5 mmol, 685.7 mg). The mixture was heated under reflux with stirring for 2 h and then filtered. The resulting clear pale yellow solution was diffused with diethyl ether vapor at room temperature for 12 days, after which large yellow blocks of (I) were obtained.

Refinement top

The H atoms were positioned geometrically (C—H = 0.93–0.96 Å, O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C, O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. The crystal packing of (I), viewed approximately along the a axis.
3-(2-Pyridylmethyleneamino)benzoic acid top
Crystal data top
C13H10N2O2F(000) = 944
Mr = 226.23Dx = 1.375 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 781 reflections
a = 27.217 (2) Åθ = 3.0–22.2°
b = 4.0536 (17) ŵ = 0.10 mm1
c = 23.767 (2) ÅT = 298 K
β = 123.553 (15)°Block, yellow
V = 2185.2 (10) Å30.59 × 0.21 × 0.13 mm
Z = 8
Data collection top
Siemens SMART CCD
diffractometer
1926 independent reflections
Radiation source: fine-focus sealed tube896 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.092
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2632
Tmin = 0.946, Tmax = 0.988k = 44
5079 measured reflectionsl = 2825
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0411P)2]
where P = (Fo2 + 2Fc2)/3
1926 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C13H10N2O2V = 2185.2 (10) Å3
Mr = 226.23Z = 8
Monoclinic, C2/cMo Kα radiation
a = 27.217 (2) ŵ = 0.10 mm1
b = 4.0536 (17) ÅT = 298 K
c = 23.767 (2) Å0.59 × 0.21 × 0.13 mm
β = 123.553 (15)°
Data collection top
Siemens SMART CCD
diffractometer
1926 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
896 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.988Rint = 0.092
5079 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.00Δρmax = 0.24 e Å3
1926 reflectionsΔρmin = 0.18 e Å3
155 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
N10.10556 (9)0.7481 (7)0.34401 (12)0.0521 (8)
N20.07264 (9)1.2019 (7)0.44507 (12)0.0514 (8)
O10.35449 (8)0.8343 (7)0.41129 (11)0.0816 (9)
O20.32303 (8)1.0085 (7)0.47445 (10)0.0703 (8)
H20.35641.08560.49740.105*
C10.31601 (12)0.8605 (9)0.42142 (16)0.0561 (10)
C20.25549 (12)0.7286 (8)0.37490 (14)0.0467 (9)
C30.21148 (11)0.7944 (8)0.38571 (14)0.0466 (9)
H30.22010.91080.42390.056*
C40.15450 (11)0.6866 (8)0.33956 (14)0.0431 (8)
C50.14323 (12)0.5086 (8)0.28483 (14)0.0501 (9)
H50.10530.42930.25450.060*
C60.18674 (13)0.4448 (10)0.27381 (15)0.0597 (10)
H60.17820.32480.23610.072*
C70.24288 (13)0.5586 (8)0.31864 (15)0.0524 (9)
H70.27230.52030.31080.063*
C80.10902 (11)0.9531 (9)0.38494 (14)0.0491 (9)
H80.14431.06560.41250.059*
C90.05954 (11)1.0241 (9)0.39133 (14)0.0439 (8)
C100.00358 (11)0.9087 (9)0.34624 (14)0.0538 (10)
H100.00490.78730.30870.065*
C110.03951 (12)0.9758 (9)0.35763 (15)0.0568 (10)
H110.07780.90170.32730.068*
C120.02658 (13)1.1499 (9)0.41295 (16)0.0581 (10)
H120.05521.19180.42190.070*
C130.03026 (13)1.2628 (9)0.45537 (15)0.0616 (11)
H130.03941.38710.49290.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0372 (14)0.070 (2)0.0529 (16)0.0010 (14)0.0276 (13)0.0067 (15)
N20.0346 (14)0.071 (2)0.0524 (15)0.0037 (14)0.0266 (13)0.0061 (15)
O10.0428 (13)0.127 (3)0.0893 (17)0.0066 (14)0.0454 (13)0.0231 (16)
O20.0356 (12)0.113 (2)0.0599 (14)0.0092 (14)0.0248 (12)0.0223 (15)
C10.041 (2)0.074 (3)0.055 (2)0.0023 (18)0.0277 (18)0.0014 (19)
C20.0362 (17)0.059 (3)0.0466 (18)0.0035 (16)0.0238 (16)0.0013 (17)
C30.0352 (17)0.064 (3)0.0426 (17)0.0080 (16)0.0230 (16)0.0004 (16)
C40.0315 (16)0.059 (3)0.0424 (17)0.0038 (16)0.0225 (15)0.0006 (17)
C50.0401 (17)0.063 (3)0.0478 (19)0.0021 (17)0.0244 (16)0.0007 (18)
C60.055 (2)0.076 (3)0.056 (2)0.001 (2)0.0359 (19)0.013 (2)
C70.0442 (19)0.068 (3)0.059 (2)0.0016 (18)0.0369 (18)0.0017 (19)
C80.0312 (16)0.068 (3)0.0505 (19)0.0021 (17)0.0240 (16)0.0008 (19)
C90.0315 (16)0.058 (2)0.0456 (18)0.0012 (16)0.0234 (15)0.0017 (17)
C100.0337 (18)0.073 (3)0.0525 (19)0.0016 (16)0.0223 (17)0.0095 (18)
C110.0328 (17)0.073 (3)0.061 (2)0.0001 (17)0.0236 (17)0.004 (2)
C120.0362 (19)0.080 (3)0.065 (2)0.0040 (18)0.0327 (18)0.003 (2)
C130.0437 (19)0.087 (3)0.060 (2)0.0037 (19)0.0326 (18)0.012 (2)
Geometric parameters (Å, º) top
N1—C81.243 (3)C5—H50.9300
N1—C41.415 (3)C6—C71.372 (4)
N2—C131.328 (3)C6—H60.9300
N2—C91.332 (3)C7—H70.9300
O1—C11.202 (3)C8—C91.465 (3)
O2—C11.311 (3)C8—H80.9300
O2—H20.8200C9—C101.372 (4)
C1—C21.486 (4)C10—C111.369 (3)
C2—C71.369 (4)C10—H100.9300
C2—C31.383 (3)C11—C121.356 (4)
C3—C41.385 (4)C11—H110.9300
C3—H30.9300C12—C131.377 (4)
C4—C51.366 (4)C12—H120.9300
C5—C61.371 (3)C13—H130.9300
C8—N1—C4120.6 (3)C2—C7—C6119.9 (3)
C13—N2—C9118.6 (3)C2—C7—H7120.1
C1—O2—H2109.5C6—C7—H7120.1
O1—C1—O2123.6 (3)N1—C8—C9122.4 (3)
O1—C1—C2123.3 (3)N1—C8—H8118.8
O2—C1—C2113.1 (2)C9—C8—H8118.8
C7—C2—C3120.2 (3)N2—C9—C10121.8 (2)
C7—C2—C1119.0 (3)N2—C9—C8115.6 (3)
C3—C2—C1120.7 (3)C10—C9—C8122.6 (3)
C2—C3—C4119.9 (3)C11—C10—C9118.7 (3)
C2—C3—H3120.1C11—C10—H10120.6
C4—C3—H3120.1C9—C10—H10120.6
C5—C4—C3119.0 (2)C12—C11—C10120.2 (3)
C5—C4—N1116.0 (3)C12—C11—H11119.9
C3—C4—N1125.0 (3)C10—C11—H11119.9
C4—C5—C6121.2 (3)C11—C12—C13117.9 (3)
C4—C5—H5119.4C11—C12—H12121.1
C6—C5—H5119.4C13—C12—H12121.1
C5—C6—C7119.8 (3)N2—C13—C12122.8 (3)
C5—C6—H6120.1N2—C13—H13118.6
C7—C6—H6120.1C12—C13—H13118.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.403.301 (3)164
O2—H2···N2ii0.821.852.664 (3)172
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1/2, y+5/2, z+1.

Experimental details

Crystal data
Chemical formulaC13H10N2O2
Mr226.23
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)27.217 (2), 4.0536 (17), 23.767 (2)
β (°) 123.553 (15)
V3)2185.2 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.59 × 0.21 × 0.13
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.946, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
5079, 1926, 896
Rint0.092
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.140, 1.00
No. of reflections1926
No. of parameters155
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.18

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.403.301 (3)164
O2—H2···N2ii0.821.852.664 (3)172
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1/2, y+5/2, z+1.
 

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