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The complete mol­ecule of the title compound, C18H18N4, is generated by crystallographic twofold rotation symmetry, with two C atoms lying on the rotation axis. The pair of pyridyl rings form a dihedral angle of 78.4 (2)° and the dihedral angle between the pyridyl ring and the central benzene ring is 110.4 (2)°. The mol­ecules are linked into a one-dimensional chain by N—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051069/hb2587sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051069/hb2587Isup2.hkl
Contains datablock I

CCDC reference: 667417

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Comment top

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.

Related literature top

For a related structure, see: Zou et al. (2003). For background, see: Tao et al. (2000); Johnson (1976).

Experimental top

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%.

Refinement top

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).

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] 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.
1,3-Bis(2-pyridylaminomethyl)benzene top
Crystal data top
C18H18N4F(000) = 616
Mr = 290.36Dx = 1.240 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 6970 reflections
a = 23.844 (5) Åθ = 3.0–27.4°
b = 7.0493 (14) ŵ = 0.08 mm1
c = 9.2504 (19) ÅT = 295 K
V = 1554.8 (6) Å3Prism, colourless
Z = 40.38 × 0.24 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1764 independent reflections
Radiation source: fine-focus sealed tube982 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 10.000 pixels mm-1θmax = 27.4°, θmin = 3.0°
ω scansh = 3030
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 99
Tmin = 0.972, Tmax = 0.979l = 1110
13887 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-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 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.14 e Å3
Crystal data top
C18H18N4V = 1554.8 (6) Å3
Mr = 290.36Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 23.844 (5) ŵ = 0.08 mm1
b = 7.0493 (14) ÅT = 295 K
c = 9.2504 (19) Å0.38 × 0.24 × 0.20 mm
Data collection top
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 = 0.979Rint = 0.056
13887 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.06Δρmax = 0.12 e Å3
1764 reflectionsΔρmin = 0.14 e Å3
101 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.14189 (6)0.6534 (2)0.52951 (13)0.0539 (4)
N20.11264 (6)0.4662 (2)0.33872 (15)0.0634 (4)
H10.11270.44490.24720.076*
C10.14448 (6)0.6112 (2)0.38823 (16)0.0475 (4)
C20.17287 (8)0.8016 (3)0.57373 (18)0.0671 (5)
H20.17020.83620.67050.081*
C30.20785 (9)0.9053 (3)0.48820 (19)0.0683 (5)
H30.22871.00560.52550.082*
C40.21115 (7)0.8558 (3)0.34387 (18)0.0612 (5)
H40.23510.92120.28220.073*
C50.17922 (7)0.7112 (3)0.29261 (17)0.0535 (5)
H50.18040.67880.19520.064*
C60.07853 (7)0.3446 (3)0.42870 (18)0.0655 (5)
H60.05790.42100.49790.079*
H70.10240.25800.48210.079*
C70.03805 (7)0.2334 (2)0.33701 (17)0.0508 (4)
C80.03766 (8)0.0384 (3)0.3357 (2)0.0702 (5)
H80.06290.02850.39290.084*
C90.00000.0582 (4)0.25000.0870 (10)
H90.00000.19010.25000.104*
C100.00000.3274 (3)0.25000.0521 (6)
H100.00000.45930.25000.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0647 (9)0.0594 (9)0.0375 (7)0.0036 (8)0.0005 (6)0.0021 (7)
N20.0714 (9)0.0758 (11)0.0429 (7)0.0207 (8)0.0084 (7)0.0091 (8)
C10.0497 (9)0.0526 (10)0.0403 (8)0.0039 (8)0.0027 (7)0.0012 (8)
C20.0911 (13)0.0693 (13)0.0410 (9)0.0153 (11)0.0001 (10)0.0067 (9)
C30.0903 (13)0.0644 (12)0.0501 (10)0.0194 (11)0.0062 (10)0.0014 (9)
C40.0708 (11)0.0641 (12)0.0486 (9)0.0100 (10)0.0030 (9)0.0111 (9)
C50.0607 (10)0.0633 (11)0.0365 (8)0.0007 (9)0.0002 (8)0.0010 (8)
C60.0687 (11)0.0769 (14)0.0509 (10)0.0132 (10)0.0037 (9)0.0077 (9)
C70.0550 (9)0.0503 (10)0.0471 (9)0.0008 (8)0.0030 (8)0.0039 (8)
C80.0798 (12)0.0558 (12)0.0751 (13)0.0114 (10)0.0052 (11)0.0086 (10)
C90.116 (2)0.0406 (16)0.105 (2)0.0000.014 (2)0.000
C100.0662 (15)0.0389 (13)0.0512 (13)0.0000.0022 (12)0.000
Geometric parameters (Å, º) top
N1—C11.3416 (19)C5—H50.9300
N1—C21.344 (2)C6—C71.505 (2)
N2—C11.353 (2)C6—H60.9700
N2—C61.445 (2)C6—H70.9700
N2—H10.8600C7—C81.375 (3)
C1—C51.402 (2)C7—C101.3819 (19)
C2—C31.362 (2)C8—C91.378 (2)
C2—H20.9300C8—H80.9300
C3—C41.382 (2)C9—H90.9300
C3—H30.9300C10—C7i1.3819 (19)
C4—C51.358 (2)C10—H100.9300
C4—H40.9300
C1—N1—C2116.33 (14)N2—C6—C7110.19 (14)
C1—N2—C6124.67 (14)N2—C6—H6109.6
C1—N2—H1117.7C7—C6—H6109.6
C6—N2—H1117.7N2—C6—H7109.6
N1—C1—N2118.11 (14)C7—C6—H7109.6
N1—C1—C5122.04 (15)H6—C6—H7108.1
N2—C1—C5119.84 (14)C8—C7—C10118.02 (18)
N1—C2—C3125.25 (16)C8—C7—C6122.00 (17)
N1—C2—H2117.4C10—C7—C6119.98 (16)
C3—C2—H2117.4C7—C8—C9120.2 (2)
C2—C3—C4117.39 (18)C7—C8—H8119.9
C2—C3—H3121.3C9—C8—H8119.9
C4—C3—H3121.3C8—C9—C8i120.7 (3)
C5—C4—C3119.68 (17)C8—C9—H9119.6
C5—C4—H4120.2C8i—C9—H9119.6
C3—C4—H4120.2C7i—C10—C7122.7 (2)
C4—C5—C1119.23 (15)C7i—C10—H10118.6
C4—C5—H5120.4C7—C10—H10118.6
C1—C5—H5120.4
C2—N1—C1—N2178.17 (15)N2—C1—C5—C4179.68 (15)
C2—N1—C1—C52.4 (2)C1—N2—C6—C7165.56 (15)
C6—N2—C1—N14.2 (2)N2—C6—C7—C8120.92 (19)
C6—N2—C1—C5175.23 (16)N2—C6—C7—C1058.67 (19)
C1—N1—C2—C32.8 (3)C10—C7—C8—C90.3 (2)
N1—C2—C3—C41.0 (3)C6—C7—C8—C9179.86 (13)
C2—C3—C4—C51.4 (3)C7—C8—C9—C8i0.14 (12)
C3—C4—C5—C11.7 (3)C8—C7—C10—C7i0.13 (12)
N1—C1—C5—C40.3 (2)C6—C7—C10—C7i179.74 (16)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···N1ii0.862.243.0625 (19)160
Symmetry code: (ii) x, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC18H18N4
Mr290.36
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)295
a, b, c (Å)23.844 (5), 7.0493 (14), 9.2504 (19)
V3)1554.8 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.38 × 0.24 × 0.20
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.972, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
13887, 1764, 982
Rint0.056
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.116, 1.06
No. of reflections1764
No. of parameters101
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.12, 0.14

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···N1i0.862.243.0625 (19)160
Symmetry code: (i) x, y+1, z1/2.
 

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