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

Abstract

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,

• 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) ų

• 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[F ² > 2σ(F ²)] = 0.041

• wR(F ²) = 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 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811044114/hb6451Isup3.cml

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

supplementary crystallographic information

Experimental

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.

Refinement

All the H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Figures

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).

Crystal data

C26H38N2	Z = 1
Mr = 378.58	F(000) = 208
Triclinic, P1	Dx = 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

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

Refinement

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(Fo2) + (0.034P)2] where P = (Fo2 + 2Fc2)/3
2686 reflections	(Δ/σ)max < 0.001
130 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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 codes: (i) −x+2, −y, −z+1.