organic compounds
N2,N2′-Bis(pyridin-2-ylmethylidene)pyridine-2,6-dicarbohydrazide dimethylformamide monosolvate
aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China
*Correspondence e-mail: fanchuangang2009@163.com
In the crystal of the title compound, C22H22N8O3, the dicarbohydrazide molecules are linked into a chain along [010] by C—H⋯N interactions involving the pyridyl N atoms and aromatic C—H groups. The DMF molecule is hydrogen bonded with the amide N—H via N—H⋯O interactions. C—H⋯O interactions also occur.
Related literature
For the biological properties of Schiff base ligands, see: Bedia et al. (2006). For related structures, see: Alhadi et al. (2008); Nie (2008).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Siemens, 2007); cell SAINT (Siemens, 2007); data reduction: SAINT; 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.
Supporting information
https://doi.org/10.1107/S1600536810039346/ds2055sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039346/ds2055Isup2.hkl
Pyridine-2,6-dicarbohydrazide (6 mmol) in DMF (20 ml) was added to pyridine-2-aldehyde (12 mmol). The mixture was refluxed with stirring for 6 h. A red precipitate was then obtained. Red crystals suitable for X-ray
formed after one week on slow evaporation of DMF solution at room temperature. Elemental analysis: calculated for C22H22N8O3: C 59.18, H 4.97, N 25.10%; found: C 59.28, H 4.82, N 25.21%.All H atoms were placed in geometrically idealized positions (N—H 0.86 and C—H = 0.93–0.96 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2U-1.5eq(C) (C,N).
Schiff bases containing pyridine ring have received considerable attention during the last decades, mainly because their steric and electronic properties can be easily adapted by choosing the right amine and aldehyde precursors(Bedia et al., 2006).
We report here the
of the title new Schiff base compound (I).In (I) (Fig. 1), the bond lengths and angles are normal and are comparable to the values observed in similar compounds (Nie et al., 2008; Alhadi et al., 2008). Meanwhile, the structure unit of (I), contains one N'2,N'6-bis(pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide molecule and one N,N-dimethylformamide solvate molecule. In molecule N'2,N'6-bis (pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide, the centre pyridine ring and the pyridine rings (n4/c9/c10/c11/c12/c13),(n1/c2/c3/c4/c5/c6) form the dihedral angles of 9.13 (15)°, 4.35 (17)°, respectively, which mean the atoms of the molecule N'2,N'6-bis (pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide are almost coplanar.
Moreover, the crystal surpermolecular structure was built from the connections of weak intermolecular N—H···O, C—H···O and C—H···N as shown in table 1.
For the biological properties of Schiff base ligands, see: Bedia et al. (2006). For related structures, see: Alhadi et al. (2008); Nie (2008).
Data collection: SMART (Siemens, 2007); cell
SAINT (Siemens, 2007); data reduction: SAINT (Siemens, 2007); 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).Fig. 1. The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids. | |
Fig. 2. The crystal packing of (I), viewed along the a axis. |
C19H15N7O2·C3H7NO | F(000) = 936 |
Mr = 446.48 | Dx = 1.321 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2269 reflections |
a = 10.0944 (9) Å | θ = 2.3–22.5° |
b = 24.639 (2) Å | µ = 0.09 mm−1 |
c = 9.6552 (8) Å | T = 298 K |
β = 110.826 (2)° | Block, red |
V = 2244.5 (3) Å3 | 0.36 × 0.31 × 0.17 mm |
Z = 4 |
Siemens SMART CCD area-detector diffractometer | 3945 independent reflections |
Radiation source: fine-focus sealed tube | 2291 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
phi and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→12 |
Tmin = 0.967, Tmax = 0.984 | k = −25→29 |
11220 measured reflections | l = −11→9 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0422P)2 + 0.8005P] where P = (Fo2 + 2Fc2)/3 |
3945 reflections | (Δ/σ)max < 0.001 |
300 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C19H15N7O2·C3H7NO | V = 2244.5 (3) Å3 |
Mr = 446.48 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0944 (9) Å | µ = 0.09 mm−1 |
b = 24.639 (2) Å | T = 298 K |
c = 9.6552 (8) Å | 0.36 × 0.31 × 0.17 mm |
β = 110.826 (2)° |
Siemens SMART CCD area-detector diffractometer | 3945 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2291 reflections with I > 2σ(I) |
Tmin = 0.967, Tmax = 0.984 | Rint = 0.040 |
11220 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.17 e Å−3 |
3945 reflections | Δρmin = −0.17 e Å−3 |
300 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 | 1.0532 (2) | 0.06010 (8) | 0.6046 (2) | 0.0399 (5) | |
N2 | 0.8597 (2) | 0.13178 (8) | 0.4467 (2) | 0.0478 (6) | |
H2 | 0.8437 | 0.1064 | 0.5000 | 0.057* | |
N3 | 0.7529 (2) | 0.16653 (8) | 0.3698 (2) | 0.0468 (6) | |
N4 | 0.3891 (2) | 0.17800 (9) | 0.3134 (3) | 0.0544 (6) | |
N5 | 0.9686 (2) | −0.00721 (8) | 0.7745 (2) | 0.0453 (5) | |
H5 | 0.9187 | 0.0193 | 0.7246 | 0.054* | |
N6 | 0.9148 (2) | −0.04071 (8) | 0.8553 (2) | 0.0446 (5) | |
N7 | 0.5832 (2) | −0.05299 (9) | 0.8981 (3) | 0.0593 (7) | |
N8 | 0.8324 (2) | 0.16209 (9) | 0.8702 (2) | 0.0538 (6) | |
O1 | 1.02185 (19) | 0.17371 (7) | 0.3714 (2) | 0.0590 (5) | |
O2 | 1.1763 (2) | −0.05273 (8) | 0.8419 (2) | 0.0643 (6) | |
O3 | 0.7810 (2) | 0.09334 (7) | 0.7038 (2) | 0.0647 (6) | |
C1 | 0.9891 (3) | 0.13729 (10) | 0.4390 (3) | 0.0435 (6) | |
C2 | 1.0946 (3) | 0.09502 (9) | 0.5217 (3) | 0.0397 (6) | |
C3 | 1.2263 (3) | 0.09326 (10) | 0.5094 (3) | 0.0483 (7) | |
H3 | 1.2512 | 0.1182 | 0.4506 | 0.058* | |
C4 | 1.3202 (3) | 0.05384 (11) | 0.5861 (3) | 0.0564 (8) | |
H4 | 1.4097 | 0.0516 | 0.5794 | 0.068* | |
C5 | 1.2802 (3) | 0.01771 (11) | 0.6728 (3) | 0.0524 (7) | |
H5A | 1.3422 | −0.0092 | 0.7256 | 0.063* | |
C6 | 1.1465 (3) | 0.02221 (9) | 0.6800 (3) | 0.0405 (6) | |
C7 | 1.1003 (3) | −0.01612 (10) | 0.7739 (3) | 0.0431 (6) | |
C8 | 0.6315 (3) | 0.15664 (10) | 0.3761 (3) | 0.0489 (7) | |
H8 | 0.6194 | 0.1272 | 0.4308 | 0.059* | |
C9 | 0.5108 (3) | 0.19145 (10) | 0.2974 (3) | 0.0454 (7) | |
C10 | 0.5215 (3) | 0.23516 (11) | 0.2119 (3) | 0.0607 (8) | |
H10 | 0.6081 | 0.2438 | 0.2036 | 0.073* | |
C11 | 0.4044 (4) | 0.26539 (12) | 0.1401 (3) | 0.0659 (9) | |
H11 | 0.4100 | 0.2950 | 0.0828 | 0.079* | |
C12 | 0.2779 (3) | 0.25150 (12) | 0.1535 (3) | 0.0621 (8) | |
H12 | 0.1958 | 0.2711 | 0.1044 | 0.075* | |
C13 | 0.2757 (3) | 0.20829 (12) | 0.2407 (3) | 0.0614 (8) | |
H13 | 0.1899 | 0.1993 | 0.2502 | 0.074* | |
C14 | 0.7866 (3) | −0.03185 (10) | 0.8425 (3) | 0.0466 (7) | |
H14 | 0.7361 | −0.0040 | 0.7815 | 0.056* | |
C15 | 0.7184 (3) | −0.06509 (10) | 0.9230 (3) | 0.0429 (6) | |
C16 | 0.7895 (3) | −0.10600 (10) | 1.0182 (3) | 0.0495 (7) | |
H16 | 0.8846 | −0.1128 | 1.0347 | 0.059* | |
C17 | 0.7184 (3) | −0.13655 (11) | 1.0882 (3) | 0.0573 (8) | |
H17 | 0.7637 | −0.1647 | 1.1513 | 0.069* | |
C18 | 0.5798 (3) | −0.12467 (12) | 1.0632 (3) | 0.0619 (8) | |
H18 | 0.5286 | −0.1446 | 1.1089 | 0.074* | |
C19 | 0.5177 (3) | −0.08291 (13) | 0.9697 (4) | 0.0680 (9) | |
H19 | 0.4237 | −0.0748 | 0.9550 | 0.082* | |
C20 | 0.7886 (3) | 0.11313 (12) | 0.8238 (3) | 0.0567 (8) | |
H20 | 0.7607 | 0.0912 | 0.8870 | 0.068* | |
C21 | 0.8856 (4) | 0.19753 (12) | 0.7832 (4) | 0.0753 (10) | |
H21A | 0.9833 | 0.1892 | 0.8016 | 0.113* | |
H21B | 0.8776 | 0.2346 | 0.8101 | 0.113* | |
H21C | 0.8314 | 0.1924 | 0.6799 | 0.113* | |
C22 | 0.8389 (4) | 0.18074 (14) | 1.0149 (4) | 0.0905 (12) | |
H22A | 0.8091 | 0.1521 | 1.0646 | 0.136* | |
H22B | 0.7774 | 0.2115 | 1.0035 | 0.136* | |
H22C | 0.9344 | 0.1910 | 1.0724 | 0.136* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0422 (12) | 0.0380 (11) | 0.0372 (12) | −0.0013 (10) | 0.0111 (10) | −0.0001 (10) |
N2 | 0.0479 (14) | 0.0483 (13) | 0.0485 (14) | 0.0057 (11) | 0.0187 (12) | 0.0119 (11) |
N3 | 0.0480 (14) | 0.0495 (13) | 0.0416 (14) | 0.0077 (11) | 0.0145 (11) | 0.0060 (11) |
N4 | 0.0495 (14) | 0.0638 (15) | 0.0505 (15) | 0.0082 (12) | 0.0186 (12) | 0.0115 (12) |
N5 | 0.0477 (13) | 0.0416 (12) | 0.0483 (14) | 0.0007 (10) | 0.0192 (11) | 0.0087 (10) |
N6 | 0.0494 (14) | 0.0399 (12) | 0.0470 (14) | −0.0032 (10) | 0.0203 (12) | 0.0024 (10) |
N7 | 0.0485 (15) | 0.0632 (15) | 0.0695 (18) | 0.0088 (12) | 0.0250 (13) | 0.0170 (13) |
N8 | 0.0674 (16) | 0.0472 (14) | 0.0459 (15) | 0.0036 (12) | 0.0189 (13) | 0.0027 (12) |
O1 | 0.0569 (12) | 0.0580 (12) | 0.0641 (14) | 0.0013 (9) | 0.0240 (11) | 0.0191 (10) |
O2 | 0.0577 (13) | 0.0570 (12) | 0.0801 (16) | 0.0126 (10) | 0.0268 (12) | 0.0261 (11) |
O3 | 0.0962 (16) | 0.0493 (11) | 0.0570 (14) | 0.0045 (11) | 0.0377 (13) | 0.0016 (10) |
C1 | 0.0471 (16) | 0.0466 (16) | 0.0365 (16) | −0.0029 (13) | 0.0144 (13) | 0.0008 (13) |
C2 | 0.0436 (15) | 0.0393 (14) | 0.0345 (15) | −0.0028 (12) | 0.0118 (12) | −0.0021 (12) |
C3 | 0.0510 (17) | 0.0504 (16) | 0.0463 (17) | −0.0022 (13) | 0.0207 (14) | 0.0058 (13) |
C4 | 0.0468 (17) | 0.0632 (18) | 0.064 (2) | 0.0018 (15) | 0.0250 (16) | 0.0072 (16) |
C5 | 0.0450 (16) | 0.0546 (17) | 0.0570 (19) | 0.0076 (13) | 0.0173 (15) | 0.0065 (15) |
C6 | 0.0443 (15) | 0.0358 (14) | 0.0386 (16) | −0.0006 (12) | 0.0113 (13) | −0.0014 (12) |
C7 | 0.0447 (16) | 0.0377 (14) | 0.0448 (17) | 0.0009 (12) | 0.0134 (14) | 0.0009 (12) |
C8 | 0.0548 (18) | 0.0493 (16) | 0.0440 (17) | 0.0065 (14) | 0.0194 (14) | 0.0116 (13) |
C9 | 0.0484 (16) | 0.0496 (16) | 0.0381 (16) | 0.0049 (13) | 0.0152 (14) | 0.0029 (13) |
C10 | 0.063 (2) | 0.0606 (19) | 0.062 (2) | 0.0068 (16) | 0.0265 (17) | 0.0139 (16) |
C11 | 0.081 (2) | 0.0568 (19) | 0.057 (2) | 0.0143 (17) | 0.0205 (18) | 0.0143 (15) |
C12 | 0.061 (2) | 0.067 (2) | 0.051 (2) | 0.0235 (17) | 0.0111 (16) | 0.0045 (16) |
C13 | 0.0514 (18) | 0.075 (2) | 0.058 (2) | 0.0107 (16) | 0.0188 (16) | 0.0044 (17) |
C14 | 0.0503 (17) | 0.0375 (14) | 0.0518 (18) | 0.0025 (13) | 0.0179 (14) | 0.0038 (13) |
C15 | 0.0437 (16) | 0.0384 (14) | 0.0444 (16) | −0.0019 (12) | 0.0128 (13) | −0.0015 (12) |
C16 | 0.0457 (16) | 0.0472 (16) | 0.0559 (18) | 0.0020 (13) | 0.0183 (14) | 0.0030 (14) |
C17 | 0.061 (2) | 0.0515 (17) | 0.057 (2) | 0.0003 (15) | 0.0191 (16) | 0.0122 (15) |
C18 | 0.059 (2) | 0.0658 (19) | 0.065 (2) | −0.0070 (16) | 0.0279 (17) | 0.0115 (17) |
C19 | 0.0472 (18) | 0.082 (2) | 0.078 (2) | 0.0073 (16) | 0.0266 (17) | 0.0209 (19) |
C20 | 0.072 (2) | 0.0517 (18) | 0.053 (2) | 0.0035 (15) | 0.0305 (17) | 0.0106 (15) |
C21 | 0.094 (3) | 0.0557 (19) | 0.086 (3) | −0.0023 (17) | 0.044 (2) | 0.0063 (18) |
C22 | 0.132 (3) | 0.083 (2) | 0.053 (2) | −0.004 (2) | 0.030 (2) | −0.0114 (18) |
N1—C2 | 1.339 (3) | C6—C7 | 1.494 (3) |
N1—C6 | 1.342 (3) | C8—C9 | 1.463 (3) |
N2—C1 | 1.342 (3) | C8—H8 | 0.9300 |
N2—N3 | 1.370 (3) | C9—C10 | 1.384 (3) |
N2—H2 | 0.8600 | C10—C11 | 1.360 (4) |
N3—C8 | 1.272 (3) | C10—H10 | 0.9300 |
N4—C9 | 1.333 (3) | C11—C12 | 1.372 (4) |
N4—C13 | 1.338 (3) | C11—H11 | 0.9300 |
N5—C7 | 1.349 (3) | C12—C13 | 1.362 (4) |
N5—N6 | 1.373 (3) | C12—H12 | 0.9300 |
N5—H5 | 0.8600 | C13—H13 | 0.9300 |
N6—C14 | 1.275 (3) | C14—C15 | 1.459 (3) |
N7—C15 | 1.332 (3) | C14—H14 | 0.9300 |
N7—C19 | 1.336 (3) | C15—C16 | 1.381 (3) |
N8—C20 | 1.308 (3) | C16—C17 | 1.373 (3) |
N8—C21 | 1.441 (3) | C16—H16 | 0.9300 |
N8—C22 | 1.450 (4) | C17—C18 | 1.364 (4) |
O1—C1 | 1.222 (3) | C17—H17 | 0.9300 |
O2—C7 | 1.215 (3) | C18—C19 | 1.365 (4) |
O3—C20 | 1.234 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.500 (3) | C19—H19 | 0.9300 |
C2—C3 | 1.377 (3) | C20—H20 | 0.9300 |
C3—C4 | 1.375 (3) | C21—H21A | 0.9600 |
C3—H3 | 0.9300 | C21—H21B | 0.9600 |
C4—C5 | 1.378 (4) | C21—H21C | 0.9600 |
C4—H4 | 0.9300 | C22—H22A | 0.9600 |
C5—C6 | 1.380 (3) | C22—H22B | 0.9600 |
C5—H5A | 0.9300 | C22—H22C | 0.9600 |
C2—N1—C6 | 117.6 (2) | C9—C10—H10 | 120.3 |
C1—N2—N3 | 120.0 (2) | C10—C11—C12 | 119.0 (3) |
C1—N2—H2 | 120.0 | C10—C11—H11 | 120.5 |
N3—N2—H2 | 120.0 | C12—C11—H11 | 120.5 |
C8—N3—N2 | 116.1 (2) | C13—C12—C11 | 118.3 (3) |
C9—N4—C13 | 116.9 (2) | C13—C12—H12 | 120.9 |
C7—N5—N6 | 119.6 (2) | C11—C12—H12 | 120.9 |
C7—N5—H5 | 120.2 | N4—C13—C12 | 124.2 (3) |
N6—N5—H5 | 120.2 | N4—C13—H13 | 117.9 |
C14—N6—N5 | 115.8 (2) | C12—C13—H13 | 117.9 |
C15—N7—C19 | 116.5 (2) | N6—C14—C15 | 120.5 (2) |
C20—N8—C21 | 120.6 (2) | N6—C14—H14 | 119.8 |
C20—N8—C22 | 121.1 (3) | C15—C14—H14 | 119.8 |
C21—N8—C22 | 118.1 (3) | N7—C15—C16 | 122.7 (2) |
O1—C1—N2 | 123.9 (2) | N7—C15—C14 | 115.1 (2) |
O1—C1—C2 | 121.2 (2) | C16—C15—C14 | 122.2 (2) |
N2—C1—C2 | 114.9 (2) | C17—C16—C15 | 119.2 (2) |
N1—C2—C3 | 123.1 (2) | C17—C16—H16 | 120.4 |
N1—C2—C1 | 116.8 (2) | C15—C16—H16 | 120.4 |
C3—C2—C1 | 120.0 (2) | C18—C17—C16 | 118.6 (3) |
C4—C3—C2 | 118.6 (2) | C18—C17—H17 | 120.7 |
C4—C3—H3 | 120.7 | C16—C17—H17 | 120.7 |
C2—C3—H3 | 120.7 | C17—C18—C19 | 118.7 (3) |
C3—C4—C5 | 119.2 (2) | C17—C18—H18 | 120.7 |
C3—C4—H4 | 120.4 | C19—C18—H18 | 120.7 |
C5—C4—H4 | 120.4 | N7—C19—C18 | 124.3 (3) |
C4—C5—C6 | 118.8 (3) | N7—C19—H19 | 117.9 |
C4—C5—H5A | 120.6 | C18—C19—H19 | 117.9 |
C6—C5—H5A | 120.6 | O3—C20—N8 | 125.9 (3) |
N1—C6—C5 | 122.6 (2) | O3—C20—H20 | 117.0 |
N1—C6—C7 | 117.3 (2) | N8—C20—H20 | 117.0 |
C5—C6—C7 | 120.1 (2) | N8—C21—H21A | 109.5 |
O2—C7—N5 | 123.5 (2) | N8—C21—H21B | 109.5 |
O2—C7—C6 | 121.6 (2) | H21A—C21—H21B | 109.5 |
N5—C7—C6 | 114.9 (2) | N8—C21—H21C | 109.5 |
N3—C8—C9 | 120.1 (2) | H21A—C21—H21C | 109.5 |
N3—C8—H8 | 119.9 | H21B—C21—H21C | 109.5 |
C9—C8—H8 | 119.9 | N8—C22—H22A | 109.5 |
N4—C9—C10 | 122.2 (2) | N8—C22—H22B | 109.5 |
N4—C9—C8 | 115.2 (2) | H22A—C22—H22B | 109.5 |
C10—C9—C8 | 122.6 (2) | N8—C22—H22C | 109.5 |
C11—C10—C9 | 119.5 (3) | H22A—C22—H22C | 109.5 |
C11—C10—H10 | 120.3 | H22B—C22—H22C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3 | 0.86 | 2.29 | 3.015 (3) | 142 |
N5—H5···O3 | 0.86 | 2.26 | 3.045 (3) | 152 |
N2—H2···O3 | 0.86 | 2.29 | 3.015 (3) | 142 |
N5—H5···O3 | 0.86 | 2.26 | 3.045 (3) | 152 |
C22—H22A···O2i | 0.96 | 2.59 | 3.469 (4) | 152 |
C12—H12···O1ii | 0.93 | 2.68 | 3.534 (3) | 153 |
C11—H11···N4iii | 0.93 | 2.62 | 3.402 (4) | 142 |
C3—H3···N4iv | 0.93 | 2.68 | 3.585 (3) | 165 |
C5—H5A···N7iv | 0.93 | 2.64 | 3.520 (4) | 158 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x−1, −y+1/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C19H15N7O2·C3H7NO |
Mr | 446.48 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.0944 (9), 24.639 (2), 9.6552 (8) |
β (°) | 110.826 (2) |
V (Å3) | 2244.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.36 × 0.31 × 0.17 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.967, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11220, 3945, 2291 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.126, 1.03 |
No. of reflections | 3945 |
No. of parameters | 300 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.17 |
Computer programs: SMART (Siemens, 2007), SAINT (Siemens, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3 | 0.86 | 2.29 | 3.015 (3) | 141.5 |
N5—H5···O3 | 0.86 | 2.26 | 3.045 (3) | 152.0 |
N2—H2···O3 | 0.86 | 2.29 | 3.015 (3) | 141.5 |
N5—H5···O3 | 0.86 | 2.26 | 3.045 (3) | 152.0 |
C22—H22A···O2i | 0.96 | 2.59 | 3.469 (4) | 151.5 |
C12—H12···O1ii | 0.93 | 2.68 | 3.534 (3) | 152.9 |
C11—H11···N4iii | 0.93 | 2.62 | 3.402 (4) | 142.2 |
C3—H3···N4iv | 0.93 | 2.68 | 3.585 (3) | 165.1 |
C5—H5A···N7iv | 0.93 | 2.64 | 3.520 (4) | 157.9 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x−1, −y+1/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) x+1, y, z. |
Acknowledgements
The authors acknowledge the financial support of the Foundation of Binzhou University (Nos. BZXYLG200609, BZXYQNLG2005013).
References
Alhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261. Web of Science CrossRef PubMed CAS Google Scholar
Nie, Y. (2008). Acta Cryst. E64, o471. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (2007). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Schiff bases containing pyridine ring have received considerable attention during the last decades, mainly because their steric and electronic properties can be easily adapted by choosing the right amine and aldehyde precursors(Bedia et al., 2006).
We report here the crystal structure of the title new Schiff base compound (I).
In (I) (Fig. 1), the bond lengths and angles are normal and are comparable to the values observed in similar compounds (Nie et al., 2008; Alhadi et al., 2008). Meanwhile, the structure unit of (I), contains one N'2,N'6-bis(pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide molecule and one N,N-dimethylformamide solvate molecule. In molecule N'2,N'6-bis (pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide, the centre pyridine ring and the pyridine rings (n4/c9/c10/c11/c12/c13),(n1/c2/c3/c4/c5/c6) form the dihedral angles of 9.13 (15)°, 4.35 (17)°, respectively, which mean the atoms of the molecule N'2,N'6-bis (pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide are almost coplanar.
Moreover, the crystal surpermolecular structure was built from the connections of weak intermolecular N—H···O, C—H···O and C—H···N as shown in table 1.