Literature DB >> 21578737

1,4-Bis{3-[4-(dimethyl-amino)benzyl-ideneamino]prop-yl}piperazine.

Rui-Bo Xu, Xing-You Xu, Da-Qi Wang, Xu-Jie Yang, Shuan Li.

Abstract

The mol-ecule of the title compound, C(28)H(42)N(6), has site symmetry with the centroid of the piperazine ring located on an inversion center. The piperazine ring adopts a chair conformation. The benzene ring and propyl-piperazine are on opposite sides of the C=N bond, showing an E configuration.

Entities: CellLine Chemical Disease Gene

Year: 2009 PMID： 21578737 PMCID： PMC2972073 DOI： 10.1107/S1600536809045619

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For applications of Schiff base compounds, see: Basak et al. (2008 ▶); Jiang et al. (2008 ▶); Xu et al. (2008 ▶). For N,N′-disubstituted piperazine derivatives, see: Yogavel et al. (2003 ▶). For related structures, see: Paital et al. (2009 ▶); Thirumurugan et al. (1998 ▶).

Experimental

Crystal data

C28H42N6 M = 462.68 Monoclinic, a = 17.599 (2) Å b = 6.4146 (12) Å c = 12.6643 (18) Å β = 105.921 (3)° V = 1374.8 (4) Å3 Z = 2 Mo Kα radiation μ = 0.07 mm−1 T = 298 K 0.15 × 0.09 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: none 6788 measured reflections 2416 independent reflections 961 reflections with I > 2σ(I) R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.095 wR(F 2) = 0.298 S = 1.34 2416 reflections 155 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.17 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045619/xu2643sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045619/xu2643Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₈H₄₂N₆	F(000) = 504
M_r = 462.68	D_x = 1.118 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 683 reflections
a = 17.599 (2) Å	θ = 2.4–49.5°
b = 6.4146 (12) Å	µ = 0.07 mm⁻¹
c = 12.6643 (18) Å	T = 298 K
β = 105.921 (3)°	Platelet, yellow
V = 1374.8 (4) Å³	0.15 × 0.09 × 0.07 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	961 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.088
graphite	θ_max = 25.0°, θ_min = 2.4°
φ and ω scans	h = −20→20
6788 measured reflections	k = −7→5
2416 independent reflections	l = −15→14

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)] = 0.095	H-atom parameters constrained
wR(F²) = 0.298	w = 1/[σ²(F_o²) + (0.0892P)²] where P = (F_o² + 2F_c²)/3
S = 1.34	(Δ/σ)_max = 0.004
2416 reflections	Δρ_max = 0.24 e Å⁻³
155 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (5)

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.

	x	y	z	U_iso*/U_eq
N1	0.9158 (3)	−0.7316 (8)	1.1684 (4)	0.0687 (16)
N2	0.7447 (3)	0.0908 (8)	0.9057 (5)	0.0667 (15)
N3	0.5629 (3)	0.4652 (7)	0.5991 (4)	0.0590 (14)
C1	0.7396 (3)	−0.0090 (10)	0.9908 (6)	0.0625 (17)
H1	0.7045	0.0408	1.0280	0.075*
C2	0.7852 (3)	−0.1960 (9)	1.0339 (5)	0.0541 (16)
C3	0.8387 (3)	−0.2867 (10)	0.9837 (5)	0.0598 (17)
H3	0.8455	−0.2295	0.9194	0.072*
C4	0.8822 (3)	−0.4629 (9)	1.0298 (5)	0.0563 (16)
H4	0.9183	−0.5194	0.9961	0.068*
C5	0.8728 (3)	−0.5567 (9)	1.1258 (5)	0.0539 (16)
C6	0.8190 (3)	−0.4665 (9)	1.1741 (5)	0.0580 (16)
H6	0.8113	−0.5255	1.2375	0.070*
C7	0.7766 (3)	−0.2905 (10)	1.1299 (5)	0.0672 (18)
H7	0.7414	−0.2333	1.1649	0.081*
C8	0.9031 (4)	−0.8320 (10)	1.2662 (5)	0.083 (2)
H8A	0.9375	−0.9505	1.2856	0.124*
H8B	0.8492	−0.8767	1.2510	0.124*
H8C	0.9145	−0.7346	1.3260	0.124*
C9	0.9638 (4)	−0.8399 (10)	1.1115 (6)	0.083 (2)
H9A	0.9889	−0.9563	1.1548	0.125*
H9B	1.0033	−0.7471	1.0993	0.125*
H9C	0.9312	−0.8890	1.0422	0.125*
C10	0.6968 (4)	0.2755 (10)	0.8724 (5)	0.0704 (19)
H10A	0.7309	0.3962	0.8784	0.084*
H10B	0.6636	0.2962	0.9214	0.084*
C11	0.6451 (4)	0.2571 (9)	0.7554 (5)	0.0665 (18)
H11A	0.6095	0.1398	0.7500	0.080*
H11B	0.6781	0.2311	0.7067	0.080*
C12	0.5971 (3)	0.4555 (9)	0.7193 (5)	0.0637 (18)
H12A	0.5548	0.4618	0.7547	0.076*
H12B	0.6309	0.5758	0.7431	0.076*
C13	0.5345 (4)	0.6762 (9)	0.5644 (5)	0.0710 (19)
H13A	0.5778	0.7745	0.5873	0.085*
H13B	0.4940	0.7152	0.5995	0.085*
C14	0.5005 (4)	0.6860 (10)	0.4399 (5)	0.0678 (18)
H14A	0.4803	0.8251	0.4189	0.081*
H14B	0.5422	0.6586	0.4051	0.081*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.081 (4)	0.071 (4)	0.055 (4)	0.017 (3)	0.020 (3)	0.013 (3)
N2	0.061 (3)	0.074 (4)	0.063 (4)	0.015 (3)	0.013 (3)	0.011 (3)
N3	0.054 (3)	0.060 (3)	0.063 (4)	0.007 (3)	0.015 (3)	0.012 (3)
C1	0.057 (4)	0.069 (4)	0.067 (5)	0.005 (3)	0.026 (3)	−0.007 (4)
C2	0.052 (3)	0.062 (4)	0.049 (4)	0.004 (3)	0.015 (3)	0.004 (3)
C3	0.062 (4)	0.067 (4)	0.052 (4)	−0.007 (3)	0.017 (3)	0.003 (3)
C4	0.057 (4)	0.062 (4)	0.052 (4)	0.003 (3)	0.019 (3)	0.001 (3)
C5	0.059 (4)	0.057 (4)	0.043 (4)	−0.007 (3)	0.009 (3)	0.003 (3)
C6	0.070 (4)	0.065 (4)	0.043 (4)	−0.005 (3)	0.023 (3)	0.000 (3)
C7	0.065 (4)	0.073 (5)	0.072 (5)	−0.002 (4)	0.033 (4)	0.003 (4)
C8	0.098 (5)	0.079 (5)	0.067 (5)	0.003 (4)	0.014 (4)	0.017 (4)
C9	0.097 (5)	0.069 (5)	0.086 (6)	0.013 (4)	0.027 (4)	0.004 (4)
C10	0.061 (4)	0.070 (5)	0.075 (5)	0.006 (3)	0.012 (4)	0.010 (4)
C11	0.069 (4)	0.067 (4)	0.068 (5)	0.012 (3)	0.026 (4)	0.015 (4)
C12	0.062 (4)	0.068 (4)	0.063 (5)	0.006 (3)	0.020 (3)	0.008 (3)
C13	0.075 (4)	0.063 (4)	0.072 (5)	0.013 (4)	0.017 (4)	0.013 (3)
C14	0.068 (4)	0.063 (4)	0.073 (5)	0.003 (4)	0.021 (4)	0.021 (4)

N1—C5	1.378 (7)	C8—H8A	0.9600
N1—C9	1.432 (7)	C8—H8B	0.9600
N1—C8	1.466 (7)	C8—H8C	0.9600
N2—C1	1.278 (7)	C9—H9A	0.9600
N2—C10	1.448 (7)	C9—H9B	0.9600
N3—C13	1.468 (7)	C9—H9C	0.9600
N3—C14ⁱ	1.459 (7)	C10—C11	1.516 (8)
N3—C12	1.477 (7)	C10—H10A	0.9700
C1—C2	1.462 (8)	C10—H10B	0.9700
C1—H1	0.9300	C11—C12	1.527 (8)
C2—C7	1.404 (7)	C11—H11A	0.9700
C2—C3	1.400 (7)	C11—H11B	0.9700
C3—C4	1.399 (8)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.407 (7)	C13—C14	1.527 (8)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.387 (8)	C13—H13B	0.9700
C6—C7	1.384 (8)	C14—N3ⁱ	1.459 (7)
C6—H6	0.9300	C14—H14A	0.9700
C7—H7	0.9300	C14—H14B	0.9700

C5—N1—C9	122.3 (5)	N1—C9—H9B	109.5
C5—N1—C8	119.7 (5)	H9A—C9—H9B	109.5
C9—N1—C8	117.3 (5)	N1—C9—H9C	109.5
C1—N2—C10	119.0 (5)	H9A—C9—H9C	109.5
C13—N3—C14ⁱ	110.2 (5)	H9B—C9—H9C	109.5
C13—N3—C12	110.9 (5)	N2—C10—C11	111.5 (5)
C14ⁱ—N3—C12	112.2 (5)	N2—C10—H10A	109.3
N2—C1—C2	124.6 (6)	C11—C10—H10A	109.3
N2—C1—H1	117.7	N2—C10—H10B	109.3
C2—C1—H1	117.7	C11—C10—H10B	109.3
C7—C2—C3	117.4 (6)	H10A—C10—H10B	108.0
C7—C2—C1	120.0 (6)	C10—C11—C12	111.2 (5)
C3—C2—C1	122.7 (6)	C10—C11—H11A	109.4
C4—C3—C2	120.4 (6)	C12—C11—H11A	109.4
C4—C3—H3	119.8	C10—C11—H11B	109.4
C2—C3—H3	119.8	C12—C11—H11B	109.4
C3—C4—C5	121.7 (6)	H11A—C11—H11B	108.0
C3—C4—H4	119.2	N3—C12—C11	112.3 (5)
C5—C4—H4	119.2	N3—C12—H12A	109.1
N1—C5—C6	122.3 (6)	C11—C12—H12A	109.1
N1—C5—C4	120.3 (6)	N3—C12—H12B	109.1
C6—C5—C4	117.4 (6)	C11—C12—H12B	109.1
C7—C6—C5	121.3 (6)	H12A—C12—H12B	107.9
C7—C6—H6	119.3	N3—C13—C14	110.6 (5)
C5—C6—H6	119.3	N3—C13—H13A	109.5
C6—C7—C2	121.9 (6)	C14—C13—H13A	109.5
C6—C7—H7	119.1	N3—C13—H13B	109.5
C2—C7—H7	119.1	C14—C13—H13B	109.5
N1—C8—H8A	109.5	H13A—C13—H13B	108.1
N1—C8—H8B	109.5	N3ⁱ—C14—C13	111.6 (5)
H8A—C8—H8B	109.5	N3ⁱ—C14—H14A	109.3
N1—C8—H8C	109.5	C13—C14—H14A	109.3
H8A—C8—H8C	109.5	N3ⁱ—C14—H14B	109.3
H8B—C8—H8C	109.5	C13—C14—H14B	109.3
N1—C9—H9A	109.5	H14A—C14—H14B	108.0

3 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Structure and dimensionality of coordination complexes correlated to piperazine conformation: from discrete [CuII2] and [CuII4] complexes to a micro1,3-N3- bridged [CuII2]n chain.

Authors: Alok Ranjan Paital; Debashree Mandal; Xiaoying Huang; Jing Li; Guillem Aromí; Debashis Ray
Journal: Dalton Trans Date: 2009-02-28 Impact factor: 4.390

3. A four-armed Schiff base: 6,6',6'',6'''-tetra-meth-oxy-2,2',2'',2'''-[methanetetra-yltetra-kis(methylenenitrilo-methyl-idyne)]tetra-phenol.

Authors: Guang-Qi Jiang; Jie Cai; Yun-Qian Zhang; Qian-Jun Zhang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-07-12