Acta Cryst. (2010). E66, o542 [ doi:10.1107/S1600536810003831 ]
The title compound, C14H13N3O2, was prepared by the reaction of 2-methoxybenzyaldehyde with nicotinic acid hydrazide in methanol. The dihedral angle between the benzene and pyridine rings is 5.9 (3)°. In the crystal structure, molecules are linked by intermolecular N-H
O hydrogen bonds, leading to the formation of chains along the c axis; adjacent chains are linked via C-HO and C-HN hydrogen bonds.
2-Methoxybenzaldehyde (1.0 mmol, 136 mg) and nicotinic acid hydrazide (1.0 mmol, 137 mg) were dissolved in methanol (30 ml). The mixture was stirred at room temperature for 1 h to give a colourless solution. After keeping the solution in air for 3 d, colourless block shaped crystals were formed.
Atom H2 was located in a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. The other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93-0.96 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C). In the absence of significant anomalous dispersion effects, Friedel pairs were merged before the final refinement.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./ci5028fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](./ci5028fig2thm.gif)
| Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines. |
| C14H13N3O2 | Dx = 1.250 Mg m−3 |
| Mr = 255.27 | Mo Kα radiation, λ = 0.71073 Å |
| Tetragonal, P43 | Cell parameters from 2214 reflections |
| Hall symbol: P 4cw | θ = 2.5–25.3° |
| a = 9.3264 (13) Å | µ = 0.09 mm−1 |
| c = 15.594 (3) Å | T = 298 K |
| V = 1356.4 (4) Å3 | Block, colourless |
| Z = 4 | 0.20 × 0.20 × 0.18 mm |
| F(000) = 536 |
| Bruker APEXII CCD area-detector diffractometer | 1519 independent reflections |
| Radiation source: fine-focus sealed tube | 1313 reflections with I > 2σ(I) |
| graphite | Rint = 0.028 |
| ω scans | θmax = 27.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −11→10 |
| Tmin = 0.983, Tmax = 0.985 | k = −4→11 |
| 6623 measured reflections | l = −19→19 |
| 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0427P)2 + 0.084P] where P = (Fo2 + 2Fc2)/3 |
| 1519 reflections | (Δ/σ)max = 0.001 |
| 176 parameters | Δρmax = 0.09 e Å−3 |
| 2 restraints | Δρmin = −0.14 e Å−3 |
| C14H13N3O2 | Z = 4 |
| Mr = 255.27 | Mo Kα radiation |
| Tetragonal, P43 | µ = 0.09 mm−1 |
| a = 9.3264 (13) Å | T = 298 K |
| c = 15.594 (3) Å | 0.20 × 0.20 × 0.18 mm |
| V = 1356.4 (4) Å3 |
| Bruker APEXII CCD area-detector diffractometer | 1519 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 1313 reflections with I > 2σ(I) |
| Tmin = 0.983, Tmax = 0.985 | Rint = 0.028 |
| 6623 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.084 | Δρmax = 0.09 e Å−3 |
| S = 1.06 | Δρmin = −0.14 e Å−3 |
| 1519 reflections | Absolute structure: ? |
| 176 parameters | Flack parameter: ? |
| 2 restraints | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | 0.54565 (17) | 0.50653 (18) | 0.21981 (11) | 0.0443 (4) | |
| N2 | 0.41517 (19) | 0.53627 (19) | 0.18161 (11) | 0.0457 (4) | |
| N3 | 0.0801 (2) | 0.6980 (3) | 0.03464 (14) | 0.0763 (7) | |
| O1 | 0.84079 (19) | 0.3686 (2) | 0.05708 (12) | 0.0681 (5) | |
| O2 | 0.33671 (17) | 0.66164 (18) | 0.29682 (10) | 0.0586 (4) | |
| C1 | 0.7782 (2) | 0.4068 (2) | 0.20059 (15) | 0.0454 (5) | |
| C2 | 0.8837 (2) | 0.3667 (2) | 0.14119 (15) | 0.0508 (5) | |
| C3 | 1.0208 (3) | 0.3312 (3) | 0.1677 (2) | 0.0635 (7) | |
| H3 | 1.0901 | 0.3046 | 0.1279 | 0.076* | |
| C4 | 1.0535 (3) | 0.3360 (3) | 0.2543 (2) | 0.0662 (7) | |
| H4 | 1.1455 | 0.3123 | 0.2724 | 0.079* | |
| C5 | 0.9519 (3) | 0.3753 (3) | 0.31421 (19) | 0.0621 (6) | |
| H5 | 0.9751 | 0.3784 | 0.3722 | 0.075* | |
| C6 | 0.8156 (3) | 0.4098 (2) | 0.28694 (15) | 0.0516 (5) | |
| H6 | 0.7469 | 0.4358 | 0.3273 | 0.062* | |
| C7 | 0.6357 (2) | 0.4433 (2) | 0.17089 (15) | 0.0466 (5) | |
| H7 | 0.6091 | 0.4202 | 0.1151 | 0.056* | |
| C8 | 0.3205 (2) | 0.6206 (2) | 0.22245 (13) | 0.0420 (5) | |
| C9 | 0.1932 (2) | 0.6646 (2) | 0.17108 (14) | 0.0428 (5) | |
| C10 | 0.0723 (3) | 0.7159 (3) | 0.21159 (16) | 0.0623 (7) | |
| H10 | 0.0690 | 0.7228 | 0.2710 | 0.075* | |
| C11 | −0.0433 (3) | 0.7567 (4) | 0.1626 (2) | 0.0797 (9) | |
| H11 | −0.1265 | 0.7907 | 0.1884 | 0.096* | |
| C12 | −0.0339 (3) | 0.7463 (4) | 0.07564 (19) | 0.0779 (9) | |
| H12 | −0.1125 | 0.7749 | 0.0432 | 0.093* | |
| C13 | 0.1914 (3) | 0.6590 (3) | 0.08281 (14) | 0.0571 (6) | |
| H13 | 0.2732 | 0.6259 | 0.0550 | 0.069* | |
| C14 | 0.9423 (4) | 0.3294 (4) | −0.0070 (2) | 0.0921 (11) | |
| H14A | 1.0234 | 0.3926 | −0.0041 | 0.138* | |
| H14B | 0.8987 | 0.3366 | −0.0626 | 0.138* | |
| H14C | 0.9734 | 0.2325 | 0.0026 | 0.138* | |
| H2 | 0.394 (3) | 0.496 (3) | 0.1309 (11) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0447 (10) | 0.0450 (9) | 0.0430 (10) | 0.0038 (8) | −0.0060 (8) | −0.0027 (8) |
| N2 | 0.0473 (10) | 0.0510 (10) | 0.0387 (10) | 0.0048 (8) | −0.0067 (8) | −0.0073 (8) |
| N3 | 0.0612 (14) | 0.118 (2) | 0.0500 (13) | 0.0151 (13) | −0.0096 (11) | 0.0096 (13) |
| O1 | 0.0652 (10) | 0.0875 (12) | 0.0516 (10) | −0.0048 (9) | 0.0080 (9) | −0.0131 (9) |
| O2 | 0.0685 (10) | 0.0673 (10) | 0.0399 (8) | 0.0156 (8) | −0.0110 (8) | −0.0140 (8) |
| C1 | 0.0491 (12) | 0.0404 (11) | 0.0468 (12) | −0.0005 (9) | 0.0015 (9) | −0.0005 (9) |
| C2 | 0.0522 (12) | 0.0462 (11) | 0.0538 (14) | −0.0060 (9) | 0.0038 (10) | −0.0048 (10) |
| C3 | 0.0490 (13) | 0.0615 (14) | 0.0799 (18) | −0.0002 (11) | 0.0098 (13) | −0.0091 (13) |
| C4 | 0.0479 (13) | 0.0646 (16) | 0.086 (2) | 0.0025 (11) | −0.0054 (14) | 0.0038 (14) |
| C5 | 0.0647 (15) | 0.0641 (15) | 0.0576 (15) | 0.0002 (12) | −0.0114 (13) | 0.0085 (12) |
| C6 | 0.0554 (13) | 0.0517 (12) | 0.0478 (13) | 0.0016 (10) | 0.0009 (10) | 0.0040 (10) |
| C7 | 0.0519 (12) | 0.0485 (11) | 0.0395 (10) | 0.0022 (9) | −0.0030 (10) | −0.0042 (9) |
| C8 | 0.0492 (11) | 0.0405 (10) | 0.0361 (11) | 0.0013 (8) | −0.0022 (9) | −0.0018 (8) |
| C9 | 0.0449 (11) | 0.0421 (10) | 0.0414 (11) | −0.0001 (8) | −0.0009 (9) | −0.0020 (9) |
| C10 | 0.0606 (16) | 0.0807 (17) | 0.0458 (14) | 0.0162 (12) | 0.0040 (12) | −0.0068 (13) |
| C11 | 0.0526 (14) | 0.111 (2) | 0.076 (2) | 0.0233 (14) | 0.0058 (14) | −0.0014 (19) |
| C12 | 0.0502 (15) | 0.114 (2) | 0.0692 (19) | 0.0146 (14) | −0.0098 (13) | 0.0141 (17) |
| C13 | 0.0467 (13) | 0.0809 (16) | 0.0439 (13) | 0.0107 (11) | 0.0008 (10) | 0.0058 (11) |
| C14 | 0.080 (2) | 0.127 (3) | 0.069 (2) | −0.0180 (19) | 0.0249 (16) | −0.0256 (19) |
| N1—C7 | 1.279 (3) | C5—C6 | 1.379 (3) |
| N1—N2 | 1.383 (2) | C5—H5 | 0.93 |
| N2—C8 | 1.343 (3) | C6—H6 | 0.93 |
| N2—H2 | 0.897 (10) | C7—H7 | 0.93 |
| N3—C12 | 1.320 (4) | C8—C9 | 1.489 (3) |
| N3—C13 | 1.332 (3) | C9—C13 | 1.378 (3) |
| O1—C2 | 1.371 (3) | C9—C10 | 1.378 (3) |
| O1—C14 | 1.424 (3) | C10—C11 | 1.375 (4) |
| O2—C8 | 1.231 (2) | C10—H10 | 0.93 |
| C1—C6 | 1.391 (3) | C11—C12 | 1.362 (4) |
| C1—C2 | 1.402 (3) | C11—H11 | 0.93 |
| C1—C7 | 1.448 (3) | C12—H12 | 0.93 |
| C2—C3 | 1.385 (3) | C13—H13 | 0.93 |
| C3—C4 | 1.385 (4) | C14—H14A | 0.96 |
| C3—H3 | 0.93 | C14—H14B | 0.96 |
| C4—C5 | 1.380 (4) | C14—H14C | 0.96 |
| C4—H4 | 0.93 | ||
| C7—N1—N2 | 114.42 (17) | C1—C7—H7 | 119.3 |
| C8—N2—N1 | 119.46 (17) | O2—C8—N2 | 123.23 (19) |
| C8—N2—H2 | 120.9 (19) | O2—C8—C9 | 121.28 (18) |
| N1—N2—H2 | 119.6 (19) | N2—C8—C9 | 115.49 (17) |
| C12—N3—C13 | 116.6 (2) | C13—C9—C10 | 117.4 (2) |
| C2—O1—C14 | 118.3 (2) | C13—C9—C8 | 122.5 (2) |
| C6—C1—C2 | 118.0 (2) | C10—C9—C8 | 120.1 (2) |
| C6—C1—C7 | 122.3 (2) | C11—C10—C9 | 118.9 (2) |
| C2—C1—C7 | 119.7 (2) | C11—C10—H10 | 120.6 |
| O1—C2—C3 | 123.9 (2) | C9—C10—H10 | 120.6 |
| O1—C2—C1 | 115.1 (2) | C12—C11—C10 | 118.8 (3) |
| C3—C2—C1 | 121.0 (2) | C12—C11—H11 | 120.6 |
| C4—C3—C2 | 119.1 (2) | C10—C11—H11 | 120.6 |
| C4—C3—H3 | 120.4 | N3—C12—C11 | 124.0 (3) |
| C2—C3—H3 | 120.4 | N3—C12—H12 | 118.0 |
| C5—C4—C3 | 121.1 (2) | C11—C12—H12 | 118.0 |
| C5—C4—H4 | 119.4 | N3—C13—C9 | 124.3 (2) |
| C3—C4—H4 | 119.4 | N3—C13—H13 | 117.9 |
| C6—C5—C4 | 119.1 (3) | C9—C13—H13 | 117.9 |
| C6—C5—H5 | 120.4 | O1—C14—H14A | 109.5 |
| C4—C5—H5 | 120.4 | O1—C14—H14B | 109.5 |
| C5—C6—C1 | 121.7 (2) | H14A—C14—H14B | 109.5 |
| C5—C6—H6 | 119.2 | O1—C14—H14C | 109.5 |
| C1—C6—H6 | 119.2 | H14A—C14—H14C | 109.5 |
| N1—C7—C1 | 121.4 (2) | H14B—C14—H14C | 109.5 |
| N1—C7—H7 | 119.3 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O2i | 0.90 (1) | 2.05 (2) | 2.897 (2) | 157 (3) |
| C4—H4···O1ii | 0.93 | 2.58 | 3.469 (3) | 160 |
| C11—H11···N3iii | 0.93 | 2.53 | 3.429 (4) | 164 |
| C13—H13···N1i | 0.93 | 2.56 | 3.487 (3) | 176 |
| Symmetry codes: (i) −y+1, x, z−1/4; (ii) y+1, −x+1, z+1/4; (iii) y−1, −x+1, z+1/4. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O2i | 0.90 (1) | 2.05 (2) | 2.897 (2) | 157 (3) |
| C4—H4···O1ii | 0.93 | 2.58 | 3.469 (3) | 160 |
| C11—H11···N3iii | 0.93 | 2.53 | 3.429 (4) | 164 |
| C13—H13···N1i | 0.93 | 2.56 | 3.487 (3) | 176 |
| Symmetry codes: (i) −y+1, x, z−1/4; (ii) y+1, −x+1, z+1/4; (iii) y−1, −x+1, z+1/4. |
The authors acknowledge the support by the Science and Technology Department of Yunnan Province, the Program of Yunnan Province's Young-Middle Aged Reserve Scientific and Technological Principal Culture Plan (grant No. 2006PY01–50) and the fund of Yunnan Province's Applied Research Plan (grant No. 2006E0032M).
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Schiff bases have been received much attention in recent years (Ogawa et al., 1998; Archibald et al., 1994; Harada et al., 1999). As a further investigation of the structures of Schiff base compounds, the title new compound is reported here.
In the title compound, the dihedral angle between the benzene ring and the pyridine ring is 5.9 (3)°. All the bond lengths are comparable with the similar Schiff bases reported previously (Wen et al., 2009; Mohd Lair et al., 2009; Sun et al., 2009).
In the crystal structure, molecules form chains running along the c axis through intermolecular N—H···O hydrogen bonds (Table 1 and Fig. 2).