1,4-Bis(4-tert-but­ylbenz­yl)piperazine

Luo, L.-J.; Weng, J.-Q.

doi:10.1107/S1600536811044114

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3094

doi:10.1107/S1600536811044114

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1,4-Bis(4-tert-butylbenzyl)piperazine

Li-Juan Luo ^a and Jian-Quan Weng ^b ^*

^aDepartment of Chemical Engineering, Ningbo University of Technology, Ningbo 315016, People's Republic of China, and ^bCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: wengjianquan@yahoo.cn

(Received 14 October 2011; accepted 24 October 2011; online 29 October 2011)

The complete molecule of the title compound, C₂₆H₃₈N₂, is generated by a crystallographic inversion centre. The piperazine ring adopts a chair conformation with pseudo-equatorial substituents. In the crystal, molecules interact only by van der Waals forces.

Related literature

For related structures, see: Ma et al. (2007 ); Liu et al. (2011 ).

Experimental

Crystal data

C₂₆H₃₈N₂
M_r = 378.58
Triclinic, $[P \overline 1]$
a = 6.162 (4) Å
b = 9.616 (5) Å
c = 10.656 (7) Å
α = 114.279 (19)°
β = 92.42 (5)°
γ = 96.50 (4)°
V = 569.1 (6) Å³
Z = 1
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.08 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.985, T_max = 0.995
6003 measured reflections
2686 independent reflections
1481 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.099
S = 1.01
2686 reflections
130 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044114/hb6451sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044114/hb6451Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044114/hb6451Isup3.cml

checkCIF report

Related literature top

For related structures, see: Ma et al. (2007); Liu et al. (2011).

Experimental top

Piperazine (50 mmol), dissolved in 20 ml 96% of ethanol, was added dropwise to a stirred solution of tert-butyl benzyl (50 mmol) at reflux. The mixture was stirred for 8 h at reflux, TLC monitored. The mixture was stirred overnight at room temperature, evaporated in vacuum and the residue was purified by recrystallization from ethanol to give the title compound, (I). Colourless prisms of (I) were grown from ethanol.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: CrystalStructure (Rigaku/MSC, 2005).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The crystal packing for (I).

1,4-Bis(4-tert-butylbenzyl)piperazine top

Crystal data top

C₂₆H₃₈N₂	Z = 1
M_r = 378.58	F(000) = 208
Triclinic, P1	D_x = 1.105 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.162 (4) Å	Cell parameters from 1980 reflections
b = 9.616 (5) Å	θ = 2.1–27.9°
c = 10.656 (7) Å	µ = 0.06 mm⁻¹
α = 114.279 (19)°	T = 113 K
β = 92.42 (5)°	Prism, colorless
γ = 96.50 (4)°	0.24 × 0.20 × 0.08 mm
V = 569.1 (6) Å³

Data collection top

Rigaku Saturn724 CCD diffractometer	2686 independent reflections
Radiation source: rotating anode	1481 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.041
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω and ϕ scans	h = −8→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→12
T_min = 0.985, T_max = 0.995	l = −13→14
6003 measured reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.034P)²] where P = (F_o² + 2F_c²)/3
2686 reflections	(Δ/σ)_max < 0.001
130 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₆H₃₈N₂	γ = 96.50 (4)°
M_r = 378.58	V = 569.1 (6) Å³
Triclinic, P1	Z = 1
a = 6.162 (4) Å	Mo Kα radiation
b = 9.616 (5) Å	µ = 0.06 mm⁻¹
c = 10.656 (7) Å	T = 113 K
α = 114.279 (19)°	0.24 × 0.20 × 0.08 mm
β = 92.42 (5)°

Data collection top

Rigaku Saturn724 CCD diffractometer	2686 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1481 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.995	R_int = 0.041
6003 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
2686 reflections	Δρ_min = −0.18 e Å⁻³
130 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
N1	1.04698 (14)	0.10740 (11)	0.64238 (9)	0.0276 (3)
C1	1.19772 (18)	0.10329 (14)	0.53912 (12)	0.0304 (3)
H1A	1.3503	0.1354	0.5835	0.036*
H1B	1.1644	0.1765	0.4999	0.036*
C2	0.82344 (17)	0.05712 (14)	0.57527 (11)	0.0296 (3)
H2A	0.7838	0.1295	0.5366	0.036*
H2B	0.7205	0.0582	0.6444	0.036*
C3	1.0687 (2)	0.26252 (14)	0.75487 (12)	0.0349 (3)
H3A	1.0114	0.3328	0.7192	0.042*
H3B	1.2260	0.3006	0.7869	0.042*
C4	0.94701 (19)	0.26622 (13)	0.87580 (11)	0.0283 (3)
C5	0.7673 (2)	0.34155 (14)	0.91236 (12)	0.0354 (3)
H5	0.7138	0.3899	0.8579	0.042*
C6	0.66197 (19)	0.34862 (14)	1.02736 (12)	0.0325 (3)
H6	0.5377	0.4012	1.0492	0.039*
C7	0.73370 (17)	0.28090 (12)	1.11086 (11)	0.0244 (3)
C8	0.91275 (17)	0.20106 (13)	1.07092 (12)	0.0301 (3)
H8	0.9643	0.1500	1.1235	0.036*
C9	1.01657 (18)	0.19463 (14)	0.95659 (12)	0.0316 (3)
H9	1.1385	0.1398	0.9328	0.038*
C10	0.62717 (18)	0.28918 (14)	1.24015 (12)	0.0292 (3)
C11	0.5127 (2)	0.12960 (15)	1.21512 (15)	0.0519 (4)
H11A	0.4028	0.0923	1.1350	0.078*
H11B	0.4404	0.1356	1.2970	0.078*
H11C	0.6212	0.0584	1.1973	0.078*
C12	0.45875 (19)	0.40197 (14)	1.28026 (12)	0.0360 (3)
H12A	0.5309	0.5053	1.2976	0.054*
H12B	0.3964	0.4045	1.3641	0.054*
H12C	0.3413	0.3683	1.2047	0.054*
C13	0.8046 (2)	0.34597 (17)	1.36335 (12)	0.0448 (4)
H13A	0.9099	0.2723	1.3441	0.067*
H13B	0.7356	0.3547	1.4469	0.067*
H13C	0.8814	0.4470	1.3774	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0278 (5)	0.0292 (6)	0.0238 (5)	0.0025 (4)	0.0087 (4)	0.0089 (5)
C1	0.0275 (6)	0.0365 (8)	0.0272 (6)	0.0022 (5)	0.0094 (5)	0.0132 (6)
C2	0.0304 (7)	0.0347 (7)	0.0274 (6)	0.0078 (5)	0.0107 (5)	0.0151 (6)
C3	0.0433 (7)	0.0305 (7)	0.0271 (7)	−0.0004 (6)	0.0118 (6)	0.0090 (6)
C4	0.0344 (7)	0.0234 (6)	0.0229 (6)	−0.0004 (5)	0.0076 (5)	0.0061 (5)
C5	0.0478 (8)	0.0366 (8)	0.0275 (7)	0.0138 (6)	0.0079 (6)	0.0167 (6)
C6	0.0359 (7)	0.0354 (7)	0.0291 (7)	0.0147 (6)	0.0092 (5)	0.0134 (6)
C7	0.0269 (6)	0.0216 (6)	0.0204 (6)	0.0006 (5)	0.0029 (5)	0.0051 (5)
C8	0.0328 (7)	0.0318 (7)	0.0276 (6)	0.0060 (5)	0.0027 (5)	0.0139 (6)
C9	0.0297 (7)	0.0330 (7)	0.0312 (7)	0.0079 (5)	0.0099 (6)	0.0111 (6)
C10	0.0345 (7)	0.0302 (7)	0.0242 (6)	0.0061 (5)	0.0088 (5)	0.0118 (5)
C11	0.0698 (10)	0.0356 (8)	0.0532 (9)	0.0059 (7)	0.0367 (8)	0.0192 (7)
C12	0.0390 (7)	0.0395 (8)	0.0278 (7)	0.0099 (6)	0.0111 (6)	0.0105 (6)
C13	0.0510 (8)	0.0611 (10)	0.0255 (7)	0.0164 (7)	0.0073 (6)	0.0190 (7)

Geometric parameters (Å, º) top

N1—C2	1.4575 (17)	C7—C8	1.3968 (16)
N1—C1	1.4609 (17)	C7—C10	1.5275 (18)
N1—C3	1.4665 (16)	C8—C9	1.3821 (17)
C1—C2ⁱ	1.5089 (17)	C8—H8	0.9500
C1—H1A	0.9900	C9—H9	0.9500
C1—H1B	0.9900	C10—C11	1.5251 (19)
C2—C1ⁱ	1.5090 (17)	C10—C12	1.5321 (17)
C2—H2A	0.9900	C10—C13	1.540 (2)
C2—H2B	0.9900	C11—H11A	0.9800
C3—C4	1.5079 (18)	C11—H11B	0.9800
C3—H3A	0.9900	C11—H11C	0.9800
C3—H3B	0.9900	C12—H12A	0.9800
C4—C5	1.3742 (17)	C12—H12B	0.9800
C4—C9	1.3863 (17)	C12—H12C	0.9800
C5—C6	1.3916 (18)	C13—H13A	0.9800
C5—H5	0.9500	C13—H13B	0.9800
C6—C7	1.3855 (17)	C13—H13C	0.9800
C6—H6	0.9500

C2—N1—C1	109.05 (10)	C8—C7—C10	119.97 (11)
C2—N1—C3	111.16 (11)	C9—C8—C7	121.48 (12)
C1—N1—C3	110.69 (10)	C9—C8—H8	119.3
N1—C1—C2ⁱ	110.36 (10)	C7—C8—H8	119.3
N1—C1—H1A	109.6	C8—C9—C4	121.58 (11)
C2ⁱ—C1—H1A	109.6	C8—C9—H9	119.2
N1—C1—H1B	109.6	C4—C9—H9	119.2
C2ⁱ—C1—H1B	109.6	C11—C10—C7	109.50 (10)
H1A—C1—H1B	108.1	C11—C10—C12	108.72 (11)
N1—C2—C1ⁱ	110.74 (11)	C7—C10—C12	112.36 (11)
N1—C2—H2A	109.5	C11—C10—C13	109.56 (12)
C1ⁱ—C2—H2A	109.5	C7—C10—C13	109.51 (10)
N1—C2—H2B	109.5	C12—C10—C13	107.14 (11)
C1ⁱ—C2—H2B	109.5	C10—C11—H11A	109.5
H2A—C2—H2B	108.1	C10—C11—H11B	109.5
N1—C3—C4	112.51 (11)	H11A—C11—H11B	109.5
N1—C3—H3A	109.1	C10—C11—H11C	109.5
C4—C3—H3A	109.1	H11A—C11—H11C	109.5
N1—C3—H3B	109.1	H11B—C11—H11C	109.5
C4—C3—H3B	109.1	C10—C12—H12A	109.5
H3A—C3—H3B	107.8	C10—C12—H12B	109.5
C5—C4—C9	117.25 (11)	H12A—C12—H12B	109.5
C5—C4—C3	122.29 (12)	C10—C12—H12C	109.5
C9—C4—C3	120.46 (11)	H12A—C12—H12C	109.5
C4—C5—C6	121.51 (12)	H12B—C12—H12C	109.5
C4—C5—H5	119.2	C10—C13—H13A	109.5
C6—C5—H5	119.2	C10—C13—H13B	109.5
C7—C6—C5	121.68 (11)	H13A—C13—H13B	109.5
C7—C6—H6	119.2	C10—C13—H13C	109.5
C5—C6—H6	119.2	H13A—C13—H13C	109.5
C6—C7—C8	116.46 (11)	H13B—C13—H13C	109.5
C6—C7—C10	123.57 (11)

C2—N1—C1—C2ⁱ	−58.15 (14)	C5—C6—C7—C10	178.35 (10)
C3—N1—C1—C2ⁱ	179.26 (9)	C6—C7—C8—C9	2.03 (16)
C1—N1—C2—C1ⁱ	58.37 (14)	C10—C7—C8—C9	−178.31 (10)
C3—N1—C2—C1ⁱ	−179.32 (10)	C7—C8—C9—C4	−0.42 (18)
C2—N1—C3—C4	68.92 (14)	C5—C4—C9—C8	−1.27 (17)
C1—N1—C3—C4	−169.72 (9)	C3—C4—C9—C8	177.64 (10)
N1—C3—C4—C5	−113.26 (14)	C6—C7—C10—C11	111.43 (14)
N1—C3—C4—C9	67.89 (15)	C8—C7—C10—C11	−68.21 (14)
C9—C4—C5—C6	1.30 (17)	C6—C7—C10—C12	−9.49 (16)
C3—C4—C5—C6	−177.58 (11)	C8—C7—C10—C12	170.87 (10)
C4—C5—C6—C7	0.36 (19)	C6—C7—C10—C13	−128.42 (13)
C5—C6—C7—C8	−2.00 (17)	C8—C7—C10—C13	51.94 (14)

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₈N₂
M_r	378.58
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	6.162 (4), 9.616 (5), 10.656 (7)
α, β, γ (°)	114.279 (19), 92.42 (5), 96.50 (4)
V (Å³)	569.1 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.24 × 0.20 × 0.08

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.985, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	6003, 2686, 1481
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.099, 1.01
No. of reflections	2686
No. of parameters	130
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

References

Liu, X.-F. & Liu, X.-H. (2011). Acta Cryst. E67, o202. Web of Science CrossRef IUCr Journals Google Scholar
Ma, H.-F., Jia, H.-S., Qian, Y., Wen, F. & Chen, B.-L. (2007). Acta Cryst. E63, o311–o312. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc. The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar