Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055754/hb2632sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055754/hb2632Isup2.hkl |
CCDC reference: 672859
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
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).
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).
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids (arbitrary spheres for the H atoms). | |
Fig. 2. The crystal packing of (I), viewed approximately along the a axis. |
C13H10N2O2 | F(000) = 944 |
Mr = 226.23 | Dx = 1.375 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 781 reflections |
a = 27.217 (2) Å | θ = 3.0–22.2° |
b = 4.0536 (17) Å | µ = 0.10 mm−1 |
c = 23.767 (2) Å | T = 298 K |
β = 123.553 (15)° | Block, yellow |
V = 2185.2 (10) Å3 | 0.59 × 0.21 × 0.13 mm |
Z = 8 |
Siemens SMART CCD diffractometer | 1926 independent reflections |
Radiation source: fine-focus sealed tube | 896 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.092 |
ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −26→32 |
Tmin = 0.946, Tmax = 0.988 | k = −4→4 |
5079 measured reflections | l = −28→25 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C13H10N2O2 | V = 2185.2 (10) Å3 |
Mr = 226.23 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 27.217 (2) Å | µ = 0.10 mm−1 |
b = 4.0536 (17) Å | T = 298 K |
c = 23.767 (2) Å | 0.59 × 0.21 × 0.13 mm |
β = 123.553 (15)° |
Siemens SMART CCD diffractometer | 1926 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 896 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.988 | Rint = 0.092 |
5079 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.24 e Å−3 |
1926 reflections | Δρmin = −0.18 e Å−3 |
155 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.10556 (9) | 0.7481 (7) | 0.34401 (12) | 0.0521 (8) | |
N2 | 0.07264 (9) | 1.2019 (7) | 0.44507 (12) | 0.0514 (8) | |
O1 | 0.35449 (8) | 0.8343 (7) | 0.41129 (11) | 0.0816 (9) | |
O2 | 0.32303 (8) | 1.0085 (7) | 0.47445 (10) | 0.0703 (8) | |
H2 | 0.3564 | 1.0856 | 0.4974 | 0.105* | |
C1 | 0.31601 (12) | 0.8605 (9) | 0.42142 (16) | 0.0561 (10) | |
C2 | 0.25549 (12) | 0.7286 (8) | 0.37490 (14) | 0.0467 (9) | |
C3 | 0.21148 (11) | 0.7944 (8) | 0.38571 (14) | 0.0466 (9) | |
H3 | 0.2201 | 0.9108 | 0.4239 | 0.056* | |
C4 | 0.15450 (11) | 0.6866 (8) | 0.33956 (14) | 0.0431 (8) | |
C5 | 0.14323 (12) | 0.5086 (8) | 0.28483 (14) | 0.0501 (9) | |
H5 | 0.1053 | 0.4293 | 0.2545 | 0.060* | |
C6 | 0.18674 (13) | 0.4448 (10) | 0.27381 (15) | 0.0597 (10) | |
H6 | 0.1782 | 0.3248 | 0.2361 | 0.072* | |
C7 | 0.24288 (13) | 0.5586 (8) | 0.31864 (15) | 0.0524 (9) | |
H7 | 0.2723 | 0.5203 | 0.3108 | 0.063* | |
C8 | 0.10902 (11) | 0.9531 (9) | 0.38494 (14) | 0.0491 (9) | |
H8 | 0.1443 | 1.0656 | 0.4125 | 0.059* | |
C9 | 0.05954 (11) | 1.0241 (9) | 0.39133 (14) | 0.0439 (8) | |
C10 | 0.00358 (11) | 0.9087 (9) | 0.34624 (14) | 0.0538 (10) | |
H10 | −0.0049 | 0.7873 | 0.3087 | 0.065* | |
C11 | −0.03951 (12) | 0.9758 (9) | 0.35763 (15) | 0.0568 (10) | |
H11 | −0.0778 | 0.9017 | 0.3273 | 0.068* | |
C12 | −0.02658 (13) | 1.1499 (9) | 0.41295 (16) | 0.0581 (10) | |
H12 | −0.0552 | 1.1918 | 0.4219 | 0.070* | |
C13 | 0.03026 (13) | 1.2628 (9) | 0.45537 (15) | 0.0616 (11) | |
H13 | 0.0394 | 1.3871 | 0.4929 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0372 (14) | 0.070 (2) | 0.0529 (16) | 0.0010 (14) | 0.0276 (13) | −0.0067 (15) |
N2 | 0.0346 (14) | 0.071 (2) | 0.0524 (15) | 0.0037 (14) | 0.0266 (13) | −0.0061 (15) |
O1 | 0.0428 (13) | 0.127 (3) | 0.0893 (17) | −0.0066 (14) | 0.0454 (13) | −0.0231 (16) |
O2 | 0.0356 (12) | 0.113 (2) | 0.0599 (14) | −0.0092 (14) | 0.0248 (12) | −0.0223 (15) |
C1 | 0.041 (2) | 0.074 (3) | 0.055 (2) | 0.0023 (18) | 0.0277 (18) | −0.0014 (19) |
C2 | 0.0362 (17) | 0.059 (3) | 0.0466 (18) | 0.0035 (16) | 0.0238 (16) | 0.0013 (17) |
C3 | 0.0352 (17) | 0.064 (3) | 0.0426 (17) | 0.0080 (16) | 0.0230 (16) | −0.0004 (16) |
C4 | 0.0315 (16) | 0.059 (3) | 0.0424 (17) | 0.0038 (16) | 0.0225 (15) | 0.0006 (17) |
C5 | 0.0401 (17) | 0.063 (3) | 0.0478 (19) | 0.0021 (17) | 0.0244 (16) | 0.0007 (18) |
C6 | 0.055 (2) | 0.076 (3) | 0.056 (2) | −0.001 (2) | 0.0359 (19) | −0.013 (2) |
C7 | 0.0442 (19) | 0.068 (3) | 0.059 (2) | 0.0016 (18) | 0.0369 (18) | −0.0017 (19) |
C8 | 0.0312 (16) | 0.068 (3) | 0.0505 (19) | −0.0021 (17) | 0.0240 (16) | 0.0008 (19) |
C9 | 0.0315 (16) | 0.058 (2) | 0.0456 (18) | 0.0012 (16) | 0.0234 (15) | −0.0017 (17) |
C10 | 0.0337 (18) | 0.073 (3) | 0.0525 (19) | −0.0016 (16) | 0.0223 (17) | −0.0095 (18) |
C11 | 0.0328 (17) | 0.073 (3) | 0.061 (2) | 0.0001 (17) | 0.0236 (17) | −0.004 (2) |
C12 | 0.0362 (19) | 0.080 (3) | 0.065 (2) | 0.0040 (18) | 0.0327 (18) | −0.003 (2) |
C13 | 0.0437 (19) | 0.087 (3) | 0.060 (2) | 0.0037 (19) | 0.0326 (18) | −0.012 (2) |
N1—C8 | 1.243 (3) | C5—H5 | 0.9300 |
N1—C4 | 1.415 (3) | C6—C7 | 1.372 (4) |
N2—C13 | 1.328 (3) | C6—H6 | 0.9300 |
N2—C9 | 1.332 (3) | C7—H7 | 0.9300 |
O1—C1 | 1.202 (3) | C8—C9 | 1.465 (3) |
O2—C1 | 1.311 (3) | C8—H8 | 0.9300 |
O2—H2 | 0.8200 | C9—C10 | 1.372 (4) |
C1—C2 | 1.486 (4) | C10—C11 | 1.369 (3) |
C2—C7 | 1.369 (4) | C10—H10 | 0.9300 |
C2—C3 | 1.383 (3) | C11—C12 | 1.356 (4) |
C3—C4 | 1.385 (4) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.377 (4) |
C4—C5 | 1.366 (4) | C12—H12 | 0.9300 |
C5—C6 | 1.371 (3) | C13—H13 | 0.9300 |
C8—N1—C4 | 120.6 (3) | C2—C7—C6 | 119.9 (3) |
C13—N2—C9 | 118.6 (3) | C2—C7—H7 | 120.1 |
C1—O2—H2 | 109.5 | C6—C7—H7 | 120.1 |
O1—C1—O2 | 123.6 (3) | N1—C8—C9 | 122.4 (3) |
O1—C1—C2 | 123.3 (3) | N1—C8—H8 | 118.8 |
O2—C1—C2 | 113.1 (2) | C9—C8—H8 | 118.8 |
C7—C2—C3 | 120.2 (3) | N2—C9—C10 | 121.8 (2) |
C7—C2—C1 | 119.0 (3) | N2—C9—C8 | 115.6 (3) |
C3—C2—C1 | 120.7 (3) | C10—C9—C8 | 122.6 (3) |
C2—C3—C4 | 119.9 (3) | C11—C10—C9 | 118.7 (3) |
C2—C3—H3 | 120.1 | C11—C10—H10 | 120.6 |
C4—C3—H3 | 120.1 | C9—C10—H10 | 120.6 |
C5—C4—C3 | 119.0 (2) | C12—C11—C10 | 120.2 (3) |
C5—C4—N1 | 116.0 (3) | C12—C11—H11 | 119.9 |
C3—C4—N1 | 125.0 (3) | C10—C11—H11 | 119.9 |
C4—C5—C6 | 121.2 (3) | C11—C12—C13 | 117.9 (3) |
C4—C5—H5 | 119.4 | C11—C12—H12 | 121.1 |
C6—C5—H5 | 119.4 | C13—C12—H12 | 121.1 |
C5—C6—C7 | 119.8 (3) | N2—C13—C12 | 122.8 (3) |
C5—C6—H6 | 120.1 | N2—C13—H13 | 118.6 |
C7—C6—H6 | 120.1 | C12—C13—H13 | 118.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.93 | 2.40 | 3.301 (3) | 164 |
O2—H2···N2ii | 0.82 | 1.85 | 2.664 (3) | 172 |
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+1/2, −y+5/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H10N2O2 |
Mr | 226.23 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 27.217 (2), 4.0536 (17), 23.767 (2) |
β (°) | 123.553 (15) |
V (Å3) | 2185.2 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.59 × 0.21 × 0.13 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.946, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5079, 1926, 896 |
Rint | 0.092 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.140, 1.00 |
No. of reflections | 1926 |
No. of parameters | 155 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.18 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.93 | 2.40 | 3.301 (3) | 164 |
O2—H2···N2ii | 0.82 | 1.85 | 2.664 (3) | 172 |
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+1/2, −y+5/2, −z+1. |
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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 C═N bond is shown by the molecule, with a C—N═C—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.