Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051069/hb2587sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051069/hb2587Isup2.hkl |
CCDC reference: 667417
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.002 Å
- R factor = 0.044
- wR factor = 0.116
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For a related structure, see: Zou et al. (2003). For background, see: Tao et al. (2000); Johnson (1976).
To a solution of isophthalaldehyde in toluene was added a solution of 2-aminopyridine in toluene. The mixture was refluxed for 10 h, and a yellow precipitate was obtained. The solid product was reduced in absolute methanol by sodium borohydride. Colourless prisms of (I) were obtained by recrystallization from methanol with a yield of 80%.
The H atoms were placed in calculated positions (C—H = 0.95–0.97 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(C, N).
Recently, N-heterocyclic complexes have attracted much attention in the area of coordination and supramolecular chemistry. Many one-dimensional, two-dimensional, and three-dimensional frameworks can be assembled through the metal coordination of pyridine-based bridging complexes (Tao et al., 2000). Accordingly, we have designed and synthesized the title molecule, (I). The corresponding molecule (Zou et al., 2003), with terephthalaldehyde instead of isophthalaldehyde, has a related structure.
The molecule of (I) (Fig. 1) is symmetrical with twofold rotation symmetry. The pair of pyridyl rings form a dihedral angle of 78.4 °. And the dihedral angle between the pyridyl ring and the central benzene ring is 110.4 °. The crystal structure is stabilized by the presence of intermolecular N—H···N hydrogen-bonding interactions (Table 1) resulting in a one-dimensional chain structure.
For a related structure, see: Zou et al. (2003). For background, see: Tao et al. (2000); Johnson (1976).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. A view of the molecular structure of (I). Displacement ellipsoids for the non-hydrogen atoms are drawn at the 50% probability level. Symmetry code: (i) -x, y, 1/2 - z. |
C18H18N4 | F(000) = 616 |
Mr = 290.36 | Dx = 1.240 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 6970 reflections |
a = 23.844 (5) Å | θ = 3.0–27.4° |
b = 7.0493 (14) Å | µ = 0.08 mm−1 |
c = 9.2504 (19) Å | T = 295 K |
V = 1554.8 (6) Å3 | Prism, colourless |
Z = 4 | 0.38 × 0.24 × 0.20 mm |
Rigaku R-AXIS RAPID diffractometer | 1764 independent reflections |
Radiation source: fine-focus sealed tube | 982 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.4°, θmin = 3.0° |
ω scans | h = −30→30 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −9→9 |
Tmin = 0.972, Tmax = 0.979 | l = −11→10 |
13887 measured reflections |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.046P)2 + 0.1871P] where P = (Fo2 + 2Fc2)/3 |
1764 reflections | (Δ/σ)max < 0.001 |
101 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C18H18N4 | V = 1554.8 (6) Å3 |
Mr = 290.36 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 23.844 (5) Å | µ = 0.08 mm−1 |
b = 7.0493 (14) Å | T = 295 K |
c = 9.2504 (19) Å | 0.38 × 0.24 × 0.20 mm |
Rigaku R-AXIS RAPID diffractometer | 1764 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 982 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.979 | Rint = 0.056 |
13887 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.12 e Å−3 |
1764 reflections | Δρmin = −0.14 e Å−3 |
101 parameters |
x | y | z | Uiso*/Ueq | ||
N1 | 0.14189 (6) | 0.6534 (2) | 0.52951 (13) | 0.0539 (4) | |
N2 | 0.11264 (6) | 0.4662 (2) | 0.33872 (15) | 0.0634 (4) | |
H1 | 0.1127 | 0.4449 | 0.2472 | 0.076* | |
C1 | 0.14448 (6) | 0.6112 (2) | 0.38823 (16) | 0.0475 (4) | |
C2 | 0.17287 (8) | 0.8016 (3) | 0.57373 (18) | 0.0671 (5) | |
H2 | 0.1702 | 0.8362 | 0.6705 | 0.081* | |
C3 | 0.20785 (9) | 0.9053 (3) | 0.48820 (19) | 0.0683 (5) | |
H3 | 0.2287 | 1.0056 | 0.5255 | 0.082* | |
C4 | 0.21115 (7) | 0.8558 (3) | 0.34387 (18) | 0.0612 (5) | |
H4 | 0.2351 | 0.9212 | 0.2822 | 0.073* | |
C5 | 0.17922 (7) | 0.7112 (3) | 0.29261 (17) | 0.0535 (5) | |
H5 | 0.1804 | 0.6788 | 0.1952 | 0.064* | |
C6 | 0.07853 (7) | 0.3446 (3) | 0.42870 (18) | 0.0655 (5) | |
H6 | 0.0579 | 0.4210 | 0.4979 | 0.079* | |
H7 | 0.1024 | 0.2580 | 0.4821 | 0.079* | |
C7 | 0.03805 (7) | 0.2334 (2) | 0.33701 (17) | 0.0508 (4) | |
C8 | 0.03766 (8) | 0.0384 (3) | 0.3357 (2) | 0.0702 (5) | |
H8 | 0.0629 | −0.0285 | 0.3929 | 0.084* | |
C9 | 0.0000 | −0.0582 (4) | 0.2500 | 0.0870 (10) | |
H9 | 0.0000 | −0.1901 | 0.2500 | 0.104* | |
C10 | 0.0000 | 0.3274 (3) | 0.2500 | 0.0521 (6) | |
H10 | 0.0000 | 0.4593 | 0.2500 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0647 (9) | 0.0594 (9) | 0.0375 (7) | −0.0036 (8) | −0.0005 (6) | −0.0021 (7) |
N2 | 0.0714 (9) | 0.0758 (11) | 0.0429 (7) | −0.0207 (8) | 0.0084 (7) | −0.0091 (8) |
C1 | 0.0497 (9) | 0.0526 (10) | 0.0403 (8) | 0.0039 (8) | −0.0027 (7) | −0.0012 (8) |
C2 | 0.0911 (13) | 0.0693 (13) | 0.0410 (9) | −0.0153 (11) | −0.0001 (10) | −0.0067 (9) |
C3 | 0.0903 (13) | 0.0644 (12) | 0.0501 (10) | −0.0194 (11) | −0.0062 (10) | −0.0014 (9) |
C4 | 0.0708 (11) | 0.0641 (12) | 0.0486 (9) | −0.0100 (10) | −0.0030 (9) | 0.0111 (9) |
C5 | 0.0607 (10) | 0.0633 (11) | 0.0365 (8) | −0.0007 (9) | −0.0002 (8) | 0.0010 (8) |
C6 | 0.0687 (11) | 0.0769 (14) | 0.0509 (10) | −0.0132 (10) | −0.0037 (9) | 0.0077 (9) |
C7 | 0.0550 (9) | 0.0503 (10) | 0.0471 (9) | −0.0008 (8) | 0.0030 (8) | 0.0039 (8) |
C8 | 0.0798 (12) | 0.0558 (12) | 0.0751 (13) | 0.0114 (10) | −0.0052 (11) | 0.0086 (10) |
C9 | 0.116 (2) | 0.0406 (16) | 0.105 (2) | 0.000 | −0.014 (2) | 0.000 |
C10 | 0.0662 (15) | 0.0389 (13) | 0.0512 (13) | 0.000 | 0.0022 (12) | 0.000 |
N1—C1 | 1.3416 (19) | C5—H5 | 0.9300 |
N1—C2 | 1.344 (2) | C6—C7 | 1.505 (2) |
N2—C1 | 1.353 (2) | C6—H6 | 0.9700 |
N2—C6 | 1.445 (2) | C6—H7 | 0.9700 |
N2—H1 | 0.8600 | C7—C8 | 1.375 (3) |
C1—C5 | 1.402 (2) | C7—C10 | 1.3819 (19) |
C2—C3 | 1.362 (2) | C8—C9 | 1.378 (2) |
C2—H2 | 0.9300 | C8—H8 | 0.9300 |
C3—C4 | 1.382 (2) | C9—H9 | 0.9300 |
C3—H3 | 0.9300 | C10—C7i | 1.3819 (19) |
C4—C5 | 1.358 (2) | C10—H10 | 0.9300 |
C4—H4 | 0.9300 | ||
C1—N1—C2 | 116.33 (14) | N2—C6—C7 | 110.19 (14) |
C1—N2—C6 | 124.67 (14) | N2—C6—H6 | 109.6 |
C1—N2—H1 | 117.7 | C7—C6—H6 | 109.6 |
C6—N2—H1 | 117.7 | N2—C6—H7 | 109.6 |
N1—C1—N2 | 118.11 (14) | C7—C6—H7 | 109.6 |
N1—C1—C5 | 122.04 (15) | H6—C6—H7 | 108.1 |
N2—C1—C5 | 119.84 (14) | C8—C7—C10 | 118.02 (18) |
N1—C2—C3 | 125.25 (16) | C8—C7—C6 | 122.00 (17) |
N1—C2—H2 | 117.4 | C10—C7—C6 | 119.98 (16) |
C3—C2—H2 | 117.4 | C7—C8—C9 | 120.2 (2) |
C2—C3—C4 | 117.39 (18) | C7—C8—H8 | 119.9 |
C2—C3—H3 | 121.3 | C9—C8—H8 | 119.9 |
C4—C3—H3 | 121.3 | C8—C9—C8i | 120.7 (3) |
C5—C4—C3 | 119.68 (17) | C8—C9—H9 | 119.6 |
C5—C4—H4 | 120.2 | C8i—C9—H9 | 119.6 |
C3—C4—H4 | 120.2 | C7i—C10—C7 | 122.7 (2) |
C4—C5—C1 | 119.23 (15) | C7i—C10—H10 | 118.6 |
C4—C5—H5 | 120.4 | C7—C10—H10 | 118.6 |
C1—C5—H5 | 120.4 | ||
C2—N1—C1—N2 | −178.17 (15) | N2—C1—C5—C4 | −179.68 (15) |
C2—N1—C1—C5 | 2.4 (2) | C1—N2—C6—C7 | 165.56 (15) |
C6—N2—C1—N1 | −4.2 (2) | N2—C6—C7—C8 | 120.92 (19) |
C6—N2—C1—C5 | 175.23 (16) | N2—C6—C7—C10 | −58.67 (19) |
C1—N1—C2—C3 | −2.8 (3) | C10—C7—C8—C9 | −0.3 (2) |
N1—C2—C3—C4 | 1.0 (3) | C6—C7—C8—C9 | −179.86 (13) |
C2—C3—C4—C5 | 1.4 (3) | C7—C8—C9—C8i | 0.14 (12) |
C3—C4—C5—C1 | −1.7 (3) | C8—C7—C10—C7i | 0.13 (12) |
N1—C1—C5—C4 | −0.3 (2) | C6—C7—C10—C7i | 179.74 (16) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···N1ii | 0.86 | 2.24 | 3.0625 (19) | 160 |
Symmetry code: (ii) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H18N4 |
Mr | 290.36 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 295 |
a, b, c (Å) | 23.844 (5), 7.0493 (14), 9.2504 (19) |
V (Å3) | 1554.8 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.38 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.972, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13887, 1764, 982 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.116, 1.06 |
No. of reflections | 1764 |
No. of parameters | 101 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.14 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···N1i | 0.86 | 2.24 | 3.0625 (19) | 160 |
Symmetry code: (i) x, −y+1, z−1/2. |
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Recently, N-heterocyclic complexes have attracted much attention in the area of coordination and supramolecular chemistry. Many one-dimensional, two-dimensional, and three-dimensional frameworks can be assembled through the metal coordination of pyridine-based bridging complexes (Tao et al., 2000). Accordingly, we have designed and synthesized the title molecule, (I). The corresponding molecule (Zou et al., 2003), with terephthalaldehyde instead of isophthalaldehyde, has a related structure.
The molecule of (I) (Fig. 1) is symmetrical with twofold rotation symmetry. The pair of pyridyl rings form a dihedral angle of 78.4 °. And the dihedral angle between the pyridyl ring and the central benzene ring is 110.4 °. The crystal structure is stabilized by the presence of intermolecular N—H···N hydrogen-bonding interactions (Table 1) resulting in a one-dimensional chain structure.