1,4-Dibenzyl-piperazine.

In the title compound, C(18)H(22)N(2), 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 inter-molecular contacts are observed in the crystal.

Related literature

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

Experimental

Crystal data

C18H22N2

M = 266.38

Orthorhombic,

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 ▶) 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 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

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

C18H22N2	Dx = 1.153 Mg m−3
Mr = 266.38	Melting point: 372 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 7.5130 (15) Å	θ = 9–13°
b = 19.127 (4) Å	µ = 0.07 mm−1
c = 21.366 (4) Å	T = 293 K
V = 3070.3 (11) Å3	Strip, colorless
Z = 8	0.30 × 0.20 × 0.10 mm
F(000) = 1152

Enraf–Nonius CAD-4 diffractometer	1650 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 25.3°, θmin = 1.9°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→22
Tmin = 0.980, Tmax = 0.993	l = −25→25
5468 measured reflections	3 standard reflections every 200 reflections
2781 independent reflections	intensity decay: 1%

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

	x	y	z	Uiso*/Ueq
N1	0.1744 (2)	0.09152 (8)	0.62991 (8)	0.0427 (5)
C1	0.6103 (3)	0.28645 (12)	0.57631 (12)	0.0604 (7)
H1A	0.6752	0.3217	0.5569	0.073*
N2	−0.1771 (2)	0.03706 (8)	0.61285 (8)	0.0432 (5)
C2	0.5050 (3)	0.24229 (12)	0.54133 (10)	0.0533 (6)
H2A	0.4989	0.2477	0.4981	0.064*
C3	0.4087 (3)	0.19002 (11)	0.57034 (10)	0.0449 (6)
H3A	0.3382	0.1604	0.5463	0.054*
C4	0.4150 (3)	0.18090 (10)	0.63433 (10)	0.0413 (5)
C5	0.5204 (3)	0.22622 (11)	0.66895 (11)	0.0542 (6)
H5A	0.5252	0.2218	0.7123	0.065*
C6	0.6185 (3)	0.27799 (12)	0.63953 (13)	0.0634 (7)
H6A	0.6908	0.3073	0.6632	0.076*
C7	0.3183 (3)	0.12199 (11)	0.66679 (10)	0.0504 (6)
H7A	0.4034	0.0855	0.6769	0.061*
H7B	0.2696	0.1393	0.7059	0.061*
C8	0.0184 (3)	0.13693 (10)	0.62714 (10)	0.0474 (6)
H8A	0.0520	0.1819	0.6098	0.057*
H8B	−0.0268	0.1446	0.6691	0.057*
C9	−0.1255 (3)	0.10464 (10)	0.58725 (10)	0.0480 (6)
H9A	−0.2282	0.1354	0.5860	0.058*
H9B	−0.0824	0.0987	0.5448	0.058*
C10	−0.0218 (3)	−0.00859 (10)	0.61446 (10)	0.0483 (6)
H10A	0.0230	−0.0154	0.5723	0.058*
H10B	−0.0551	−0.0539	0.6313	0.058*
C11	0.1210 (3)	0.02366 (10)	0.65474 (10)	0.0478 (6)
H11A	0.0768	0.0293	0.6971	0.057*
H11B	0.2235	−0.0072	0.6562	0.057*
C12	−0.3259 (3)	0.00581 (11)	0.57907 (10)	0.0497 (6)
H12A	−0.2825	−0.0132	0.5399	0.060*
H12B	−0.4116	0.0421	0.5692	0.060*
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	−0.0954	0.5408	0.059*
C15	−0.6260 (3)	−0.14791 (12)	0.61664 (12)	0.0569 (6)
H15A	−0.7012	−0.1782	0.5952	0.068*
C16	−0.6102 (3)	−0.15299 (11)	0.68032 (12)	0.0555 (6)
H16A	−0.6745	−0.1866	0.7022	0.067*
C17	−0.4989 (3)	−0.10828 (11)	0.71169 (10)	0.0505 (6)
H17A	−0.4870	−0.1119	0.7549	0.061*
C18	−0.4041 (3)	−0.05765 (11)	0.67923 (10)	0.0440 (6)
H18A	−0.3295	−0.0274	0.7010	0.053*

	U11	U22	U33	U12	U13	U23
N1	0.0338 (10)	0.0385 (10)	0.0558 (11)	−0.0001 (8)	−0.0015 (8)	0.0068 (8)
C1	0.0516 (15)	0.0518 (15)	0.0779 (18)	−0.0086 (12)	0.0179 (14)	−0.0005 (14)
N2	0.0328 (9)	0.0414 (10)	0.0553 (11)	0.0003 (9)	−0.0012 (9)	0.0073 (9)
C2	0.0508 (14)	0.0543 (14)	0.0547 (14)	−0.0011 (13)	0.0103 (12)	0.0035 (11)
C3	0.0366 (12)	0.0465 (13)	0.0516 (14)	−0.0022 (10)	−0.0013 (10)	−0.0029 (11)
C4	0.0316 (11)	0.0426 (12)	0.0496 (13)	0.0028 (10)	−0.0007 (10)	−0.0019 (10)
C5	0.0519 (15)	0.0588 (15)	0.0520 (14)	−0.0035 (13)	−0.0045 (12)	−0.0074 (11)
C6	0.0495 (15)	0.0580 (16)	0.0826 (19)	−0.0142 (13)	−0.0008 (13)	−0.0161 (14)
C7	0.0457 (13)	0.0516 (13)	0.0541 (13)	−0.0050 (11)	−0.0061 (12)	0.0070 (11)
C8	0.0430 (13)	0.0377 (11)	0.0614 (14)	0.0003 (11)	0.0046 (11)	0.0055 (11)
C9	0.0363 (13)	0.0431 (13)	0.0645 (14)	0.0021 (10)	−0.0021 (11)	0.0114 (11)
C10	0.0402 (13)	0.0389 (12)	0.0658 (15)	0.0006 (10)	0.0027 (11)	0.0046 (11)
C11	0.0382 (12)	0.0422 (13)	0.0629 (14)	0.0030 (10)	−0.0014 (11)	0.0118 (11)
C12	0.0423 (13)	0.0561 (14)	0.0508 (13)	−0.0035 (11)	−0.0036 (11)	0.0066 (11)
C13	0.0308 (11)	0.0449 (12)	0.0432 (12)	0.0024 (10)	−0.0008 (10)	−0.0015 (10)
C14	0.0494 (14)	0.0521 (14)	0.0468 (12)	−0.0022 (12)	−0.0062 (11)	−0.0047 (11)
C15	0.0457 (14)	0.0484 (14)	0.0768 (17)	−0.0097 (12)	−0.0082 (12)	−0.0078 (13)
C16	0.0444 (14)	0.0506 (14)	0.0715 (17)	−0.0052 (12)	0.0107 (12)	0.0068 (12)
C17	0.0425 (14)	0.0584 (14)	0.0505 (13)	0.0004 (12)	0.0039 (11)	0.0055 (11)
C18	0.0345 (12)	0.0480 (13)	0.0495 (13)	−0.0042 (10)	0.0009 (10)	−0.0045 (10)

N1—C11	1.458 (2)	C8—H8B	0.9700
N1—C7	1.459 (3)	C9—H9A	0.9700
N1—C8	1.460 (3)	C9—H9B	0.9700
C1—C6	1.362 (3)	C10—C11	1.508 (3)
C1—C2	1.377 (3)	C10—H10A	0.9700
C1—H1A	0.9300	C10—H10B	0.9700
N2—C9	1.456 (2)	C11—H11A	0.9700
N2—C10	1.457 (3)	C11—H11B	0.9700
N2—C12	1.459 (3)	C12—C13	1.512 (3)
C2—C3	1.381 (3)	C12—H12A	0.9700
C2—H2A	0.9300	C12—H12B	0.9700
C3—C4	1.379 (3)	C13—C18	1.379 (3)
C3—H3A	0.9300	C13—C14	1.389 (3)
C4—C5	1.388 (3)	C14—C15	1.381 (3)
C4—C7	1.509 (3)	C14—H14A	0.9300
C5—C6	1.385 (3)	C15—C16	1.369 (3)
C5—H5A	0.9300	C15—H15A	0.9300
C6—H6A	0.9300	C16—C17	1.371 (3)
C7—H7A	0.9700	C16—H16A	0.9300
C7—H7B	0.9700	C17—C18	1.388 (3)
C8—C9	1.509 (3)	C17—H17A	0.9300
C8—H8A	0.9700	C18—H18A	0.9300
C11—N1—C7	111.26 (16)	N2—C9—H9B	109.7
C11—N1—C8	108.88 (16)	C8—C9—H9B	109.7
C7—N1—C8	112.29 (16)	H9A—C9—H9B	108.2
C6—C1—C2	119.4 (2)	N2—C10—C11	109.76 (17)
C6—C1—H1A	120.3	N2—C10—H10A	109.7
C2—C1—H1A	120.3	C11—C10—H10A	109.7
C9—N2—C10	109.14 (16)	N2—C10—H10B	109.7
C9—N2—C12	112.43 (16)	C11—C10—H10B	109.7
C10—N2—C12	112.31 (16)	H10A—C10—H10B	108.2
C1—C2—C3	120.1 (2)	N1—C11—C10	110.62 (17)
C1—C2—H2A	120.0	N1—C11—H11A	109.5
C3—C2—H2A	120.0	C10—C11—H11A	109.5
C4—C3—C2	121.2 (2)	N1—C11—H11B	109.5
C4—C3—H3A	119.4	C10—C11—H11B	109.5
C2—C3—H3A	119.4	H11A—C11—H11B	108.1
C3—C4—C5	118.0 (2)	N2—C12—C13	113.54 (17)
C3—C4—C7	122.24 (19)	N2—C12—H12A	108.9
C5—C4—C7	119.7 (2)	C13—C12—H12A	108.9
C6—C5—C4	120.6 (2)	N2—C12—H12B	108.9
C6—C5—H5A	119.7	C13—C12—H12B	108.9
C4—C5—H5A	119.7	H12A—C12—H12B	107.7
C1—C6—C5	120.7 (2)	C18—C13—C14	117.88 (19)
C1—C6—H6A	119.6	C18—C13—C12	122.00 (18)
C5—C6—H6A	119.6	C14—C13—C12	120.04 (19)
N1—C7—C4	113.99 (17)	C15—C14—C13	121.1 (2)
N1—C7—H7A	108.8	C15—C14—H14A	119.5
C4—C7—H7A	108.8	C13—C14—H14A	119.5
N1—C7—H7B	108.8	C16—C15—C14	120.2 (2)
C4—C7—H7B	108.8	C16—C15—H15A	119.9
H7A—C7—H7B	107.6	C14—C15—H15A	119.9
N1—C8—C9	110.77 (16)	C15—C16—C17	119.6 (2)
N1—C8—H8A	109.5	C15—C16—H16A	120.2
C9—C8—H8A	109.5	C17—C16—H16A	120.2
N1—C8—H8B	109.5	C16—C17—C18	120.3 (2)
C9—C8—H8B	109.5	C16—C17—H17A	119.9
H8A—C8—H8B	108.1	C18—C17—H17A	119.9
N2—C9—C8	109.98 (17)	C13—C18—C17	120.9 (2)
N2—C9—H9A	109.7	C13—C18—H18A	119.5
C8—C9—H9A	109.7	C17—C18—H18A	119.5
C6—C1—C2—C3	0.1 (3)	C9—N2—C10—C11	59.7 (2)
C1—C2—C3—C4	0.1 (3)	C12—N2—C10—C11	−174.95 (16)
C2—C3—C4—C5	0.4 (3)	C7—N1—C11—C10	−177.43 (17)
C2—C3—C4—C7	−176.9 (2)	C8—N1—C11—C10	58.3 (2)
C3—C4—C5—C6	−1.2 (3)	N2—C10—C11—N1	−60.0 (2)
C7—C4—C5—C6	176.1 (2)	C9—N2—C12—C13	−162.08 (17)
C2—C1—C6—C5	−0.9 (4)	C10—N2—C12—C13	74.4 (2)
C4—C5—C6—C1	1.5 (4)	N2—C12—C13—C18	20.0 (3)
C11—N1—C7—C4	163.51 (17)	N2—C12—C13—C14	−163.34 (18)
C8—N1—C7—C4	−74.2 (2)	C18—C13—C14—C15	1.0 (3)
C3—C4—C7—N1	−19.8 (3)	C12—C13—C14—C15	−175.73 (19)
C5—C4—C7—N1	162.96 (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—C9	178.46 (16)	C15—C16—C17—C18	0.6 (3)
C10—N2—C9—C8	−59.3 (2)	C14—C13—C18—C17	−0.5 (3)
C12—N2—C9—C8	175.41 (17)	C12—C13—C18—C17	176.23 (19)
N1—C8—C9—N2	59.1 (2)	C16—C17—C18—C13	−0.4 (3)