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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o252.
Published online 2007 December 12. doi:  10.1107/S1600536807063878
PMCID: PMC2915309

A monoclinic polymorph of 1,3-bis­(2-pyridylamino­meth­yl)benzene

Abstract

The mol­ecules of the title compound, C18H18N4, are linked by two different N—H(...)Npyrid­yl hydrogen bonds into a linear chain.

Related literature

In the ortho­rhom­bic polymorph, the mol­ecule lies on a twofold rotation axis; adjacent mol­ecules are hydrogen-bonded into a linear chain, see: Zhu et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o252-scheme1.jpg

Experimental

Crystal data

  • C18H18N4
  • M r = 290.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o252-efi1.jpg
  • a = 35.647 (2) Å
  • b = 5.7899 (4) Å
  • c = 14.9019 (9) Å
  • β = 94.074 (2)°
  • V = 3067.9 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 (2) K
  • 0.32 × 0.28 × 0.24 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.589, T max = 0.982
  • 13991 measured reflections
  • 3512 independent reflections
  • 1833 reflections with I > 2σ(I)
  • R int = 0.047

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.150
  • S = 1.02
  • 3512 reflections
  • 208 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2007 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063878/sg2210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063878/sg2210Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Heilongjiang Province Natural Science Foundation (No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this work.

supplementary crystallographic information

Experimental

The compound was synthesized as described (Zhu et al., 2007), and crystals were obtained upon recrystallization from methanol.

Refinement

Carbon-bound H atoms were placed in calculated positions [C—H 0.93–0.97 Å and Uiso(H) 1.25Ueq(C), were included in the refinement in the riding-model approximation. The nitrogen-bound H atoms were located and difference Fourier map and were refined with a distance restraint of N–H 0.86±0.01 Å.

Figures

Fig. 1.
Thermal ellipsoid plot of a portion of the hydrogen-bonded structure; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius.

Crystal data

C18H18N4F(000) = 1232
Mr = 290.36Dx = 1.257 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7473 reflections
a = 35.647 (2) Åθ = 3.0–27.5°
b = 5.7899 (4) ŵ = 0.08 mm1
c = 14.9019 (9) ÅT = 295 K
β = 94.074 (2)°Prism, colorless
V = 3067.9 (3) Å30.32 × 0.28 × 0.24 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID diffractometer3512 independent reflections
Radiation source: fine-focus sealed tube1833 reflections with I > 2σ(I)
graphiteRint = 0.047
Detector resolution: 10.000 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω–scansh = −46→46
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −7→7
Tmin = 0.589, Tmax = 0.982l = −19→19
13991 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.150w = 1/[σ2(Fo2) + (0.0752P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3512 reflectionsΔρmax = 0.18 e Å3
208 parametersΔρmin = −0.17 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0013 (5)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.26513 (4)0.1786 (3)0.38622 (11)0.0551 (4)
N20.28167 (4)0.5057 (3)0.46611 (11)0.0571 (4)
H2N0.2672 (5)0.452 (3)0.5052 (12)0.076 (7)*
N30.47595 (4)0.7010 (3)0.58328 (13)0.0615 (5)
H3N0.4725 (6)0.599 (3)0.5412 (11)0.080 (7)*
N40.53909 (4)0.6575 (3)0.56996 (12)0.0632 (5)
C10.27020 (6)0.0330 (4)0.31870 (14)0.0648 (6)
H10.2536−0.09030.31020.078*
C20.29845 (6)0.0538 (4)0.26093 (14)0.0717 (6)
H20.3009−0.05170.21460.086*
C30.32289 (6)0.2357 (4)0.27402 (15)0.0682 (6)
H30.34240.25420.23640.082*
C40.31870 (5)0.3903 (4)0.34224 (14)0.0597 (5)
H40.33520.51410.35130.072*
C50.28904 (5)0.3579 (3)0.39817 (12)0.0491 (4)
C60.30779 (5)0.6811 (3)0.49945 (14)0.0566 (5)
H6A0.29500.78080.53980.068*
H6B0.31440.77470.44900.068*
C70.34377 (5)0.5957 (3)0.54853 (12)0.0469 (4)
C80.34573 (6)0.3867 (3)0.59374 (13)0.0566 (5)
H80.32490.28980.59120.068*
C90.37829 (6)0.3207 (3)0.64242 (15)0.0630 (6)
H90.37920.18030.67280.076*
C100.40950 (5)0.4621 (3)0.64621 (13)0.0601 (5)
H100.43130.41710.67960.072*
C110.40859 (5)0.6714 (3)0.60048 (12)0.0496 (5)
C120.37567 (5)0.7345 (3)0.55229 (12)0.0480 (4)
H120.37480.87410.52140.058*
C130.44274 (5)0.8269 (3)0.60434 (15)0.0573 (5)
H13A0.43840.95270.56190.069*
H13B0.44660.89280.66410.069*
C140.51105 (5)0.7920 (3)0.59598 (13)0.0525 (5)
C150.51840 (5)1.0098 (3)0.63396 (13)0.0600 (5)
H150.49871.10560.64820.072*
C160.55490 (6)1.0800 (4)0.64988 (14)0.0664 (6)
H160.56021.22430.67510.080*
C170.58374 (6)0.9363 (4)0.62849 (15)0.0667 (6)
H170.60880.97780.64120.080*
C180.57426 (6)0.7309 (4)0.58794 (16)0.0681 (6)
H180.59370.63570.57180.082*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0488 (9)0.0608 (10)0.0551 (10)−0.0034 (7)0.0003 (7)−0.0014 (8)
N20.0473 (9)0.0641 (10)0.0604 (10)−0.0077 (8)0.0084 (8)−0.0103 (9)
N30.0474 (9)0.0637 (11)0.0737 (12)−0.0021 (8)0.0062 (8)−0.0216 (9)
N40.0485 (10)0.0596 (10)0.0820 (12)−0.0003 (7)0.0071 (9)−0.0096 (9)
C10.0689 (13)0.0630 (12)0.0615 (12)−0.0010 (10)−0.0031 (11)−0.0067 (10)
C20.0773 (15)0.0803 (15)0.0573 (13)0.0147 (12)0.0043 (12)−0.0080 (11)
C30.0612 (13)0.0913 (15)0.0530 (12)0.0132 (12)0.0111 (10)0.0059 (12)
C40.0474 (11)0.0717 (12)0.0603 (12)−0.0037 (9)0.0058 (9)0.0065 (10)
C50.0391 (9)0.0574 (10)0.0503 (10)0.0008 (8)−0.0006 (8)0.0036 (9)
C60.0507 (11)0.0534 (11)0.0649 (12)−0.0010 (9)−0.0013 (9)−0.0014 (9)
C70.0471 (10)0.0456 (10)0.0484 (10)0.0008 (8)0.0054 (8)−0.0038 (8)
C80.0578 (12)0.0499 (11)0.0628 (12)−0.0049 (9)0.0086 (10)0.0036 (9)
C90.0671 (13)0.0556 (12)0.0666 (13)0.0046 (10)0.0052 (11)0.0162 (10)
C100.0543 (12)0.0654 (12)0.0600 (12)0.0093 (10)−0.0009 (10)0.0063 (10)
C110.0487 (11)0.0519 (10)0.0486 (10)0.0042 (8)0.0065 (9)−0.0029 (8)
C120.0507 (10)0.0437 (9)0.0500 (10)0.0027 (8)0.0056 (8)0.0009 (8)
C130.0468 (11)0.0598 (11)0.0648 (12)0.0014 (9)0.0011 (9)−0.0083 (10)
C140.0478 (11)0.0531 (11)0.0563 (11)−0.0012 (8)0.0014 (9)−0.0037 (9)
C150.0580 (12)0.0596 (12)0.0618 (12)−0.0011 (9)0.0008 (10)−0.0120 (10)
C160.0708 (14)0.0676 (13)0.0598 (12)−0.0146 (11)−0.0022 (11)−0.0083 (10)
C170.0519 (12)0.0822 (14)0.0650 (13)−0.0120 (11)−0.0034 (10)0.0022 (11)
C180.0488 (12)0.0708 (13)0.0848 (16)0.0002 (10)0.0050 (11)−0.0039 (12)

Geometric parameters (Å, °)

N1—C11.335 (2)C7—C81.384 (2)
N1—C51.347 (2)C7—C121.390 (2)
N2—C51.365 (2)C8—C91.378 (3)
N2—C61.442 (2)C8—H80.9300
N2—H2N0.86 (1)C9—C101.379 (3)
N3—C141.358 (2)C9—H90.9300
N3—C131.444 (2)C10—C111.389 (2)
N3—H3N0.86 (1)C10—H100.9300
N4—C181.333 (2)C11—C121.381 (3)
N4—C141.346 (2)C11—C131.512 (2)
C1—C21.376 (3)C12—H120.9300
C1—H10.9300C13—H13A0.9700
C2—C31.372 (3)C13—H13B0.9700
C2—H20.9300C14—C151.399 (3)
C3—C41.371 (3)C15—C161.368 (3)
C3—H30.9300C15—H150.9300
C4—C51.405 (2)C16—C171.377 (3)
C4—H40.9300C16—H160.9300
C6—C71.514 (3)C17—C181.366 (3)
C6—H6A0.9700C17—H170.9300
C6—H6B0.9700C18—H180.9300
C1—N1—C5117.91 (15)C7—C8—H8119.7
C5—N2—C6122.91 (15)C8—C9—C10120.23 (18)
C5—N2—H2N115.5 (15)C8—C9—H9119.9
C6—N2—H2N115.1 (15)C10—C9—H9119.9
C14—N3—C13122.39 (16)C9—C10—C11120.47 (19)
C14—N3—H3N116.7 (14)C9—C10—H10119.8
C13—N3—H3N115.2 (15)C11—C10—H10119.8
C18—N4—C14117.70 (17)C12—C11—C10118.35 (17)
N1—C1—C2124.1 (2)C12—C11—C13120.98 (16)
N1—C1—H1118.0C10—C11—C13120.67 (17)
C2—C1—H1118.0C11—C12—C7122.05 (16)
C3—C2—C1117.6 (2)C11—C12—H12119.0
C3—C2—H2121.2C7—C12—H12119.0
C1—C2—H2121.2N3—C13—C11111.21 (15)
C4—C3—C2120.34 (18)N3—C13—H13A109.4
C4—C3—H3119.8C11—C13—H13A109.4
C2—C3—H3119.8N3—C13—H13B109.4
C3—C4—C5118.65 (19)C11—C13—H13B109.4
C3—C4—H4120.7H13A—C13—H13B108.0
C5—C4—H4120.7N4—C14—N3115.54 (16)
N1—C5—N2115.33 (14)N4—C14—C15121.11 (17)
N1—C5—C4121.35 (17)N3—C14—C15123.36 (16)
N2—C5—C4123.30 (17)C16—C15—C14119.09 (18)
N2—C6—C7116.16 (15)C16—C15—H15120.5
N2—C6—H6A108.2C14—C15—H15120.5
C7—C6—H6A108.2C15—C16—C17119.81 (19)
N2—C6—H6B108.2C15—C16—H16120.1
C7—C6—H6B108.2C17—C16—H16120.1
H6A—C6—H6B107.4C18—C17—C16117.59 (19)
C8—C7—C12118.21 (17)C18—C17—H17121.2
C8—C7—C6122.17 (16)C16—C17—H17121.2
C12—C7—C6119.55 (15)N4—C18—C17124.49 (18)
C9—C8—C7120.67 (17)N4—C18—H18117.8
C9—C8—H8119.7C17—C18—H18117.8
C5—N1—C1—C20.4 (3)C9—C10—C11—C13−179.93 (17)
N1—C1—C2—C30.2 (3)C10—C11—C12—C70.1 (3)
C1—C2—C3—C4−0.4 (3)C13—C11—C12—C7−179.27 (16)
C2—C3—C4—C50.1 (3)C8—C7—C12—C11−1.0 (3)
C1—N1—C5—N2177.71 (17)C6—C7—C12—C11176.15 (16)
C1—N1—C5—C4−0.7 (3)C14—N3—C13—C11−169.32 (18)
C6—N2—C5—N1168.25 (17)C12—C11—C13—N3−130.03 (18)
C6—N2—C5—C4−13.4 (3)C10—C11—C13—N350.6 (2)
C3—C4—C5—N10.4 (3)C18—N4—C14—N3−174.51 (19)
C3—C4—C5—N2−177.85 (19)C18—N4—C14—C155.1 (3)
C5—N2—C6—C7−67.6 (2)C13—N3—C14—N4−177.51 (17)
N2—C6—C7—C8−27.6 (2)C13—N3—C14—C152.9 (3)
N2—C6—C7—C12155.37 (16)N4—C14—C15—C16−4.1 (3)
C12—C7—C8—C91.2 (3)N3—C14—C15—C16175.4 (2)
C6—C7—C8—C9−175.93 (18)C14—C15—C16—C170.0 (3)
C7—C8—C9—C10−0.4 (3)C15—C16—C17—C182.9 (3)
C8—C9—C10—C11−0.6 (3)C14—N4—C18—C17−2.1 (3)
C9—C10—C11—C120.7 (3)C16—C17—C18—N4−1.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2N···N1i0.86 (1)2.19 (1)3.047 (2)175 (2)
N3—H3N···N4ii0.86 (1)2.24 (1)3.104 (2)177 (2)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2210).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku Corporation (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (1997). SHELXL97 and SHELXS97 University of Göttingen, Germany.
  • Westrip, S. P. (2007). publCIF In preparation.
  • Zhu, L.-N., Gao, S. & Huo, L.-H. (2007). Acta Cryst. E63, o4399.

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