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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3336.
Published online 2010 November 27. doi:  10.1107/S1600536810049111
PMCID: PMC3011390

1,4-Dibenzyl­piperazine

Abstract

In the title compound, C18H22N2, which possesses non-crystallographic inversion symmetry, the central piperazine ring adopts a chair conformation. The phenyl rings are not exactly parallel and make a dihedral angle of 1.3 (1)°. No significant inter­molecular contacts are observed in the crystal.

Related literature

For the properties and applications of piperazine derivatives, see: Zhao et al. (2002 [triangle]); Sonurlikar et al. (1977 [triangle]); Bigoli et al. (2001 [triangle]). For the synthesis of related compounds, see: Zheng et al. (2005 [triangle]); Sarangarajan et al. (2005 [triangle]). For related structures, see: Yogavel et al. (2003 [triangle]); Gunasekaran et al. (1996 [triangle]); Thiru­murugan et al. (1998 [triangle]).

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Object name is e-66-o3336-scheme1.jpg

Experimental

Crystal data

  • C18H22N2
  • M r = 266.38
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3336-efi1.jpg
  • a = 7.5130 (15) Å
  • b = 19.127 (4) Å
  • c = 21.366 (4) Å
  • V = 3070.3 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.980, T max = 0.993
  • 5468 measured reflections
  • 2781 independent reflections
  • 1650 reflections with I > 2σ(I)
  • R int = 0.045
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.141
  • S = 1.01
  • 2781 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049111/bh2322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049111/bh2322Isup2.hkl

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

Acknowledgments

This work was supported by the 948 program of the State Forestry Administration (2009–4–55).

supplementary crystallographic information

Comment

The structural study of piperazine derivatives is of interest, because some piperazine-containing derivatives constitute a novel class of mixed D2/D4 receptor antagonists (Zhao et al., 2002), and disubstituted piperazine derivatives are antifilarial, antiamoebic and spermicidal agents (Sonurlikar et al., 1977). In addition, piperazine derivatives are useful precursors of mixed-ligand dithiolenes of interest for non-linear optics (Bigoli et al., 2001). Recently, many piperazine derivatives with various substituents have been synthesized (Zheng et al., 2005; Sarangarajan et al., 2005). Herein, we report the crystal structure of the title compound, (I).

The geometry and labeling scheme of the title compound are depicted in Fig. 1, and the packing structure is given in Fig. 2. The piperazine ring exhibits a chair conformation with the usual bond lengths and angles (Yogavel et al., 2003), comparable with those of related reported structures (Gunasekaran et al., 1996; Thirumurugan et al., 1998).

Experimental

To a solution of anhydrous piperazine (5 mmol, 0.43 g) in CH2Cl2 (20 ml) was added 2.2 equivalents of triethylamine (1.5 ml), followed by benzyl bromide (10 mmol, 2.66 g) in CH2Cl2 (20 ml). After the mixture had been stirred for 10 min., the solvent was removed using a rotary evaporator. The solid residue was washed with water and recrystallized from ethanol-cyclohexane to give a colourless solid (76% yield). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and Uiso(H) = 1.2 Ueq of the carrier atom.

Figures

Fig. 1.
A view of the molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
The packing of the title compound, viewed along the a axis.

Crystal data

C18H22N2Dx = 1.153 Mg m3
Mr = 266.38Melting point: 372 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 7.5130 (15) Åθ = 9–13°
b = 19.127 (4) ŵ = 0.07 mm1
c = 21.366 (4) ÅT = 293 K
V = 3070.3 (11) Å3Strip, colorless
Z = 80.30 × 0.20 × 0.10 mm
F(000) = 1152

Data collection

Enraf–Nonius CAD-4 diffractometer1650 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
graphiteθmax = 25.3°, θmin = 1.9°
ω/2θ scansh = 0→9
Absorption correction: ψ scan (North et al., 1968)k = 0→22
Tmin = 0.980, Tmax = 0.993l = −25→25
5468 measured reflections3 standard reflections every 200 reflections
2781 independent reflections intensity decay: 1%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.141w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2781 reflectionsΔρmax = 0.16 e Å3
182 parametersΔρmin = −0.13 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0097 (11)
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
N10.1744 (2)0.09152 (8)0.62991 (8)0.0427 (5)
C10.6103 (3)0.28645 (12)0.57631 (12)0.0604 (7)
H1A0.67520.32170.55690.073*
N2−0.1771 (2)0.03706 (8)0.61285 (8)0.0432 (5)
C20.5050 (3)0.24229 (12)0.54133 (10)0.0533 (6)
H2A0.49890.24770.49810.064*
C30.4087 (3)0.19002 (11)0.57034 (10)0.0449 (6)
H3A0.33820.16040.54630.054*
C40.4150 (3)0.18090 (10)0.63433 (10)0.0413 (5)
C50.5204 (3)0.22622 (11)0.66895 (11)0.0542 (6)
H5A0.52520.22180.71230.065*
C60.6185 (3)0.27799 (12)0.63953 (13)0.0634 (7)
H6A0.69080.30730.66320.076*
C70.3183 (3)0.12199 (11)0.66679 (10)0.0504 (6)
H7A0.40340.08550.67690.061*
H7B0.26960.13930.70590.061*
C80.0184 (3)0.13693 (10)0.62714 (10)0.0474 (6)
H8A0.05200.18190.60980.057*
H8B−0.02680.14460.66910.057*
C9−0.1255 (3)0.10464 (10)0.58725 (10)0.0480 (6)
H9A−0.22820.13540.58600.058*
H9B−0.08240.09870.54480.058*
C10−0.0218 (3)−0.00859 (10)0.61446 (10)0.0483 (6)
H10A0.0230−0.01540.57230.058*
H10B−0.0551−0.05390.63130.058*
C110.1210 (3)0.02366 (10)0.65474 (10)0.0478 (6)
H11A0.07680.02930.69710.057*
H11B0.2235−0.00720.65620.057*
C12−0.3259 (3)0.00581 (11)0.57907 (10)0.0497 (6)
H12A−0.2825−0.01320.53990.060*
H12B−0.41160.04210.56920.060*
C13−0.4189 (3)−0.05156 (10)0.61511 (9)0.0396 (5)
C14−0.5306 (3)−0.09799 (11)0.58415 (10)0.0494 (6)
H14A−0.5413−0.09540.54080.059*
C15−0.6260 (3)−0.14791 (12)0.61664 (12)0.0569 (6)
H15A−0.7012−0.17820.59520.068*
C16−0.6102 (3)−0.15299 (11)0.68032 (12)0.0555 (6)
H16A−0.6745−0.18660.70220.067*
C17−0.4989 (3)−0.10828 (11)0.71169 (10)0.0505 (6)
H17A−0.4870−0.11190.75490.061*
C18−0.4041 (3)−0.05765 (11)0.67923 (10)0.0440 (6)
H18A−0.3295−0.02740.70100.053*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0338 (10)0.0385 (10)0.0558 (11)−0.0001 (8)−0.0015 (8)0.0068 (8)
C10.0516 (15)0.0518 (15)0.0779 (18)−0.0086 (12)0.0179 (14)−0.0005 (14)
N20.0328 (9)0.0414 (10)0.0553 (11)0.0003 (9)−0.0012 (9)0.0073 (9)
C20.0508 (14)0.0543 (14)0.0547 (14)−0.0011 (13)0.0103 (12)0.0035 (11)
C30.0366 (12)0.0465 (13)0.0516 (14)−0.0022 (10)−0.0013 (10)−0.0029 (11)
C40.0316 (11)0.0426 (12)0.0496 (13)0.0028 (10)−0.0007 (10)−0.0019 (10)
C50.0519 (15)0.0588 (15)0.0520 (14)−0.0035 (13)−0.0045 (12)−0.0074 (11)
C60.0495 (15)0.0580 (16)0.0826 (19)−0.0142 (13)−0.0008 (13)−0.0161 (14)
C70.0457 (13)0.0516 (13)0.0541 (13)−0.0050 (11)−0.0061 (12)0.0070 (11)
C80.0430 (13)0.0377 (11)0.0614 (14)0.0003 (11)0.0046 (11)0.0055 (11)
C90.0363 (13)0.0431 (13)0.0645 (14)0.0021 (10)−0.0021 (11)0.0114 (11)
C100.0402 (13)0.0389 (12)0.0658 (15)0.0006 (10)0.0027 (11)0.0046 (11)
C110.0382 (12)0.0422 (13)0.0629 (14)0.0030 (10)−0.0014 (11)0.0118 (11)
C120.0423 (13)0.0561 (14)0.0508 (13)−0.0035 (11)−0.0036 (11)0.0066 (11)
C130.0308 (11)0.0449 (12)0.0432 (12)0.0024 (10)−0.0008 (10)−0.0015 (10)
C140.0494 (14)0.0521 (14)0.0468 (12)−0.0022 (12)−0.0062 (11)−0.0047 (11)
C150.0457 (14)0.0484 (14)0.0768 (17)−0.0097 (12)−0.0082 (12)−0.0078 (13)
C160.0444 (14)0.0506 (14)0.0715 (17)−0.0052 (12)0.0107 (12)0.0068 (12)
C170.0425 (14)0.0584 (14)0.0505 (13)0.0004 (12)0.0039 (11)0.0055 (11)
C180.0345 (12)0.0480 (13)0.0495 (13)−0.0042 (10)0.0009 (10)−0.0045 (10)

Geometric parameters (Å, °)

N1—C111.458 (2)C8—H8B0.9700
N1—C71.459 (3)C9—H9A0.9700
N1—C81.460 (3)C9—H9B0.9700
C1—C61.362 (3)C10—C111.508 (3)
C1—C21.377 (3)C10—H10A0.9700
C1—H1A0.9300C10—H10B0.9700
N2—C91.456 (2)C11—H11A0.9700
N2—C101.457 (3)C11—H11B0.9700
N2—C121.459 (3)C12—C131.512 (3)
C2—C31.381 (3)C12—H12A0.9700
C2—H2A0.9300C12—H12B0.9700
C3—C41.379 (3)C13—C181.379 (3)
C3—H3A0.9300C13—C141.389 (3)
C4—C51.388 (3)C14—C151.381 (3)
C4—C71.509 (3)C14—H14A0.9300
C5—C61.385 (3)C15—C161.369 (3)
C5—H5A0.9300C15—H15A0.9300
C6—H6A0.9300C16—C171.371 (3)
C7—H7A0.9700C16—H16A0.9300
C7—H7B0.9700C17—C181.388 (3)
C8—C91.509 (3)C17—H17A0.9300
C8—H8A0.9700C18—H18A0.9300
C11—N1—C7111.26 (16)N2—C9—H9B109.7
C11—N1—C8108.88 (16)C8—C9—H9B109.7
C7—N1—C8112.29 (16)H9A—C9—H9B108.2
C6—C1—C2119.4 (2)N2—C10—C11109.76 (17)
C6—C1—H1A120.3N2—C10—H10A109.7
C2—C1—H1A120.3C11—C10—H10A109.7
C9—N2—C10109.14 (16)N2—C10—H10B109.7
C9—N2—C12112.43 (16)C11—C10—H10B109.7
C10—N2—C12112.31 (16)H10A—C10—H10B108.2
C1—C2—C3120.1 (2)N1—C11—C10110.62 (17)
C1—C2—H2A120.0N1—C11—H11A109.5
C3—C2—H2A120.0C10—C11—H11A109.5
C4—C3—C2121.2 (2)N1—C11—H11B109.5
C4—C3—H3A119.4C10—C11—H11B109.5
C2—C3—H3A119.4H11A—C11—H11B108.1
C3—C4—C5118.0 (2)N2—C12—C13113.54 (17)
C3—C4—C7122.24 (19)N2—C12—H12A108.9
C5—C4—C7119.7 (2)C13—C12—H12A108.9
C6—C5—C4120.6 (2)N2—C12—H12B108.9
C6—C5—H5A119.7C13—C12—H12B108.9
C4—C5—H5A119.7H12A—C12—H12B107.7
C1—C6—C5120.7 (2)C18—C13—C14117.88 (19)
C1—C6—H6A119.6C18—C13—C12122.00 (18)
C5—C6—H6A119.6C14—C13—C12120.04 (19)
N1—C7—C4113.99 (17)C15—C14—C13121.1 (2)
N1—C7—H7A108.8C15—C14—H14A119.5
C4—C7—H7A108.8C13—C14—H14A119.5
N1—C7—H7B108.8C16—C15—C14120.2 (2)
C4—C7—H7B108.8C16—C15—H15A119.9
H7A—C7—H7B107.6C14—C15—H15A119.9
N1—C8—C9110.77 (16)C15—C16—C17119.6 (2)
N1—C8—H8A109.5C15—C16—H16A120.2
C9—C8—H8A109.5C17—C16—H16A120.2
N1—C8—H8B109.5C16—C17—C18120.3 (2)
C9—C8—H8B109.5C16—C17—H17A119.9
H8A—C8—H8B108.1C18—C17—H17A119.9
N2—C9—C8109.98 (17)C13—C18—C17120.9 (2)
N2—C9—H9A109.7C13—C18—H18A119.5
C8—C9—H9A109.7C17—C18—H18A119.5
C6—C1—C2—C30.1 (3)C9—N2—C10—C1159.7 (2)
C1—C2—C3—C40.1 (3)C12—N2—C10—C11−174.95 (16)
C2—C3—C4—C50.4 (3)C7—N1—C11—C10−177.43 (17)
C2—C3—C4—C7−176.9 (2)C8—N1—C11—C1058.3 (2)
C3—C4—C5—C6−1.2 (3)N2—C10—C11—N1−60.0 (2)
C7—C4—C5—C6176.1 (2)C9—N2—C12—C13−162.08 (17)
C2—C1—C6—C5−0.9 (4)C10—N2—C12—C1374.4 (2)
C4—C5—C6—C11.5 (4)N2—C12—C13—C1820.0 (3)
C11—N1—C7—C4163.51 (17)N2—C12—C13—C14−163.34 (18)
C8—N1—C7—C4−74.2 (2)C18—C13—C14—C151.0 (3)
C3—C4—C7—N1−19.8 (3)C12—C13—C14—C15−175.73 (19)
C5—C4—C7—N1162.96 (18)C13—C14—C15—C16−0.8 (3)
C11—N1—C8—C9−57.9 (2)C14—C15—C16—C17−0.1 (3)
C7—N1—C8—C9178.46 (16)C15—C16—C17—C180.6 (3)
C10—N2—C9—C8−59.3 (2)C14—C13—C18—C17−0.5 (3)
C12—N2—C9—C8175.41 (17)C12—C13—C18—C17176.23 (19)
N1—C8—C9—N259.1 (2)C16—C17—C18—C13−0.4 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2322).

References

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Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography