N,N′-Bis(2-cyano­ethyl)-4,4′-dimethyl-N,N′-(butane-1,4-di­yl)dibenzene­sulfonamide

Cheng, P.-F.; Wang, C.-J.; Wang, Y.-X.

doi:10.1107/S1600536809036022

organic compounds

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Volume 65| Part 10| October 2009| Page o2433

doi:10.1107/S1600536809036022

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N,N′-Bis(2-cyanoethyl)-4,4′-dimethyl-N,N′-(butane-1,4-diyl)dibenzenesulfonamide

Peng-Fei Cheng,^a Chao-Jie Wang ^a and Yu-Xia Wang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, People's Republic of China
^*Correspondence e-mail: hgxywyx@163.com

(Received 6 September 2009; accepted 6 September 2009; online 12 September 2009)

The complete molecule of the title compound, C₂₄H₃₀N₄O₄S₂, is generated by a crystallographic inversion centre. In the crystal, weak C—H⋯O interactions link the molecules, forming infinite sheets.

Related literature

For background to polyamines, see: Thomas & Thomas (2003 ).

Experimental

Crystal data

C₂₄H₃₀N₄O₄S₂
M_r = 502.64
Monoclinic, P 2₁ /c
a = 16.688 (13) Å
b = 5.786 (5) Å
c = 13.675 (11) Å
β = 104.005 (13)°
V = 1281.3 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.34 × 0.26 × 0.21 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.921, T_max = 0.950
6684 measured reflections
2510 independent reflections
2114 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.104
S = 1.05
2510 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2ⁱ	0.93	2.54	3.271 (4)	136
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036022/hb5089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036022/hb5089Isup2.hkl

checkCIF report

Comment top

Polyamines are natural products and have interesting biological activities. It present in the majority of cells. They play important roles in the synthesis of proteins, cell division, and bind to nucleic acids resulting in their condensation, thereby affecting gene expression. These effects might have implications in cancer treatment (e.g. Thomas & Thomas, 2003). We now report the crystal structure of the title compound, (I).

As shown in Fig.1, the title compound consists of two 4-methylbenzenesulfonyl groups anchoring to polyamine chain. In the structure of (I), the two phenyl ring of two 4-methylbenzenesulfonyl groups are antiparallel by symmetry.

In the crystal, the molecules are linked into infinite sheets by intermolecular C–H···O hydrogen bonds (Fig. 2).

Related literature top

For background to polyamines, see: Thomas & Thomas (2003).

Experimental top

To a solution of 1,4-diaminobutane (8.8 g, 0.1 mol) in MeOH (300 ml), acrylonitrile (11.66 g, 0.22 mol) was added dropwise at room temperature during 1 h. After stirring for additional 7 h, the solvent was evaporated. The residue was fractionated in vacuum, yielding 17.27 g (89%) of N,N'-bis(2-cyanoethyl)-1,4-diaminobutane.

To a mixture of N,N'-bis(2-cyanoethyl)-1,4-diaminobutane (17.27 g, 89 mmol) and Et₃N (17.98 g, 178 mmol) in THF (120 ml), a solution of 4-methylbenzenesulfonyl chloride (TsCl, 34.02 g, 178 mmol) in THF (120 ml) was added dropwise at room temperature. The precipitate was filtered off and discarded. The filtrate was subsequently washed with 4 mol/L NaOH (in order to hydrolyze any unreacted TsCl) and NaCl solution. Evaporation gave the target compound (I) as colourless rods (43.34 g, 97%).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level. Atoms with the suffix a are generated by (–x, 1–y, 1–z).
	Fig. 2. One-dimensional structure of (I) along c axis, Hydrogen bonds are shown as dashed lines.

N,N'-Bis(2-cyanoethyl)-4,4'-dimethyl-N,N'- (butane-1,4-diyl)dibenzenesulfonamide top

Crystal data top

C₂₄H₃₀N₄O₄S₂	F(000) = 532
M_r = 502.64	D_x = 1.303 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2757 reflections
a = 16.688 (13) Å	θ = 3.0–27.6°
b = 5.786 (5) Å	µ = 0.25 mm⁻¹
c = 13.675 (11) Å	T = 296 K
β = 104.005 (13)°	Rod, colorless
V = 1281.3 (17) Å³	0.34 × 0.26 × 0.21 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	2510 independent reflections
Radiation source: fine-focus sealed tube	2114 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −16→20
T_min = 0.921, T_max = 0.950	k = −7→7
6684 measured reflections	l = −16→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0583P)² + 0.2525P] where P = (F_o² + 2F_c²)/3
2510 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₄H₃₀N₄O₄S₂	V = 1281.3 (17) Å³
M_r = 502.64	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.688 (13) Å	µ = 0.25 mm⁻¹
b = 5.786 (5) Å	T = 296 K
c = 13.675 (11) Å	0.34 × 0.26 × 0.21 mm
β = 104.005 (13)°

Data collection top

Bruker SMART CCD diffractometer	2510 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2114 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.950	R_int = 0.019
6684 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
2510 reflections	Δρ_min = −0.29 e Å⁻³
155 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
S1	0.24666 (2)	0.32320 (7)	0.53380 (3)	0.03878 (15)
O1	0.20256 (7)	0.1573 (2)	0.57929 (10)	0.0506 (3)
O2	0.30224 (8)	0.2415 (2)	0.47571 (10)	0.0558 (3)
N1	0.17969 (8)	0.4914 (2)	0.46127 (10)	0.0392 (3)
N2	0.09678 (12)	0.0954 (3)	0.26259 (14)	0.0718 (5)
C1	0.30449 (9)	0.4988 (3)	0.63262 (12)	0.0371 (4)
C2	0.33821 (10)	0.7065 (3)	0.61032 (13)	0.0469 (4)
H2A	0.3275	0.7592	0.5442	0.056*
C3	0.38797 (11)	0.8344 (3)	0.68757 (15)	0.0532 (5)
H3A	0.4108	0.9727	0.6725	0.064*
C4	0.40431 (10)	0.7595 (4)	0.78710 (14)	0.0496 (4)
C5	0.36879 (11)	0.5538 (4)	0.80728 (13)	0.0541 (5)
H5A	0.3787	0.5020	0.8735	0.065*
C6	0.31883 (11)	0.4232 (3)	0.73143 (13)	0.0498 (4)
H6A	0.2952	0.2865	0.7468	0.060*
C7	0.45863 (13)	0.8996 (4)	0.87086 (16)	0.0720 (6)
H7A	0.4839	1.0233	0.8423	0.108*
H7B	0.5008	0.8020	0.9103	0.108*
H7C	0.4257	0.9625	0.9131	0.108*
C8	0.03371 (9)	0.4433 (3)	0.47933 (13)	0.0450 (4)
H8A	0.0144	0.4254	0.4069	0.054*
H8B	0.0455	0.2908	0.5087	0.054*
C9	0.11282 (9)	0.5880 (3)	0.50313 (12)	0.0429 (4)
H9A	0.0999	0.7425	0.4765	0.052*
H9B	0.1326	0.6008	0.5757	0.052*
C10	0.19632 (11)	0.5953 (3)	0.37044 (13)	0.0469 (4)
H10A	0.2493	0.5407	0.3622	0.056*
H10B	0.1997	0.7618	0.3785	0.056*
C11	0.12903 (12)	0.5356 (3)	0.27550 (12)	0.0497 (4)
H11A	0.0788	0.6183	0.2772	0.060*
H11B	0.1466	0.5868	0.2164	0.060*
C12	0.11145 (12)	0.2864 (4)	0.26701 (13)	0.0499 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0360 (2)	0.0370 (3)	0.0428 (2)	0.00198 (15)	0.00858 (17)	−0.00311 (16)
O1	0.0517 (7)	0.0410 (7)	0.0564 (7)	−0.0076 (5)	0.0077 (6)	0.0045 (5)
O2	0.0506 (7)	0.0601 (8)	0.0597 (7)	0.0117 (6)	0.0191 (6)	−0.0116 (7)
N1	0.0341 (7)	0.0462 (8)	0.0371 (7)	0.0025 (6)	0.0086 (5)	−0.0004 (6)
N2	0.0825 (13)	0.0529 (11)	0.0736 (12)	−0.0051 (10)	0.0062 (10)	−0.0087 (9)
C1	0.0296 (7)	0.0394 (9)	0.0420 (8)	0.0018 (6)	0.0080 (6)	−0.0010 (7)
C2	0.0475 (9)	0.0444 (10)	0.0470 (9)	−0.0020 (8)	0.0075 (8)	0.0057 (8)
C3	0.0520 (10)	0.0429 (10)	0.0627 (12)	−0.0099 (8)	0.0100 (9)	−0.0004 (8)
C4	0.0377 (9)	0.0570 (11)	0.0531 (10)	−0.0020 (8)	0.0092 (8)	−0.0103 (9)
C5	0.0539 (10)	0.0667 (13)	0.0400 (9)	−0.0098 (9)	0.0078 (8)	−0.0006 (9)
C6	0.0490 (10)	0.0542 (11)	0.0464 (9)	−0.0109 (8)	0.0118 (8)	0.0035 (8)
C7	0.0594 (12)	0.0813 (16)	0.0688 (14)	−0.0156 (11)	0.0033 (10)	−0.0215 (12)
C8	0.0369 (8)	0.0532 (11)	0.0440 (9)	0.0028 (8)	0.0078 (7)	−0.0079 (8)
C9	0.0371 (8)	0.0465 (10)	0.0441 (9)	0.0045 (7)	0.0077 (7)	−0.0060 (8)
C10	0.0493 (10)	0.0462 (10)	0.0465 (9)	−0.0050 (8)	0.0140 (8)	0.0028 (8)
C11	0.0633 (11)	0.0454 (10)	0.0388 (9)	0.0042 (8)	0.0092 (8)	0.0056 (7)
C12	0.0549 (11)	0.0527 (12)	0.0395 (9)	0.0032 (9)	0.0062 (8)	−0.0036 (8)

Geometric parameters (Å, º) top

S1—O1	1.4392 (14)	C6—H6A	0.9300
S1—O2	1.4393 (14)	C7—H7A	0.9600
S1—N1	1.6259 (15)	C7—H7B	0.9600
S1—C1	1.7772 (18)	C7—H7C	0.9600
N1—C10	1.466 (2)	C8—C8ⁱ	1.524 (3)
N1—C9	1.481 (2)	C8—C9	1.530 (2)
N2—C12	1.130 (3)	C8—H8A	0.9700
C1—C6	1.385 (2)	C8—H8B	0.9700
C1—C2	1.392 (2)	C9—H9A	0.9700
C2—C3	1.389 (3)	C9—H9B	0.9700
C2—H2A	0.9300	C10—C11	1.536 (2)
C3—C4	1.391 (3)	C10—H10A	0.9700
C3—H3A	0.9300	C10—H10B	0.9700
C4—C5	1.387 (3)	C11—C12	1.471 (3)
C4—C7	1.513 (3)	C11—H11A	0.9700
C5—C6	1.387 (3)	C11—H11B	0.9700
C5—H5A	0.9300

O1—S1—O2	118.99 (9)	H7A—C7—H7B	109.5
O1—S1—N1	108.36 (9)	C4—C7—H7C	109.5
O2—S1—N1	107.44 (9)	H7A—C7—H7C	109.5
O1—S1—C1	107.02 (9)	H7B—C7—H7C	109.5
O2—S1—C1	107.68 (9)	C8ⁱ—C8—C9	111.23 (18)
N1—S1—C1	106.75 (9)	C8ⁱ—C8—H8A	109.4
C10—N1—C9	119.19 (14)	C9—C8—H8A	109.4
C10—N1—S1	121.28 (12)	C8ⁱ—C8—H8B	109.4
C9—N1—S1	117.45 (11)	C9—C8—H8B	109.4
C6—C1—C2	120.19 (16)	H8A—C8—H8B	108.0
C6—C1—S1	119.69 (14)	N1—C9—C8	113.80 (14)
C2—C1—S1	120.06 (13)	N1—C9—H9A	108.8
C3—C2—C1	119.52 (17)	C8—C9—H9A	108.8
C3—C2—H2A	120.2	N1—C9—H9B	108.8
C1—C2—H2A	120.2	C8—C9—H9B	108.8
C2—C3—C4	121.16 (18)	H9A—C9—H9B	107.7
C2—C3—H3A	119.4	N1—C10—C11	111.99 (15)
C4—C3—H3A	119.4	N1—C10—H10A	109.2
C5—C4—C3	118.05 (17)	C11—C10—H10A	109.2
C5—C4—C7	121.07 (18)	N1—C10—H10B	109.2
C3—C4—C7	120.88 (19)	C11—C10—H10B	109.2
C4—C5—C6	121.83 (17)	H10A—C10—H10B	107.9
C4—C5—H5A	119.1	C12—C11—C10	112.22 (15)
C6—C5—H5A	119.1	C12—C11—H11A	109.2
C1—C6—C5	119.23 (18)	C10—C11—H11A	109.2
C1—C6—H6A	120.4	C12—C11—H11B	109.2
C5—C6—H6A	120.4	C10—C11—H11B	109.2
C4—C7—H7A	109.5	H11A—C11—H11B	107.9
C4—C7—H7B	109.5	N2—C12—C11	178.0 (2)

O1—S1—N1—C10	−149.35 (13)	C1—C2—C3—C4	−0.4 (3)
O2—S1—N1—C10	−19.60 (15)	C2—C3—C4—C5	−0.6 (3)
C1—S1—N1—C10	95.68 (14)	C2—C3—C4—C7	179.95 (17)
O1—S1—N1—C9	47.17 (14)	C3—C4—C5—C6	0.5 (3)
O2—S1—N1—C9	176.93 (11)	C7—C4—C5—C6	179.98 (18)
C1—S1—N1—C9	−67.79 (13)	C2—C1—C6—C5	−1.6 (3)
O1—S1—C1—C6	17.62 (16)	S1—C1—C6—C5	175.56 (13)
O2—S1—C1—C6	−111.40 (15)	C4—C5—C6—C1	0.6 (3)
N1—S1—C1—C6	133.48 (14)	C10—N1—C9—C8	102.87 (18)
O1—S1—C1—C2	−165.17 (13)	S1—N1—C9—C8	−93.29 (15)
O2—S1—C1—C2	65.80 (15)	C8ⁱ—C8—C9—N1	−177.68 (17)
N1—S1—C1—C2	−49.32 (15)	C9—N1—C10—C11	−73.0 (2)
C6—C1—C2—C3	1.6 (3)	S1—N1—C10—C11	123.77 (15)
S1—C1—C2—C3	−175.62 (13)	N1—C10—C11—C12	−50.0 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2ⁱⁱ	0.93	2.54	3.271 (4)	136

Symmetry code: (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₃₀N₄O₄S₂
M_r	502.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.688 (13), 5.786 (5), 13.675 (11)
β (°)	104.005 (13)
V (Å³)	1281.3 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.34 × 0.26 × 0.21

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.921, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	6684, 2510, 2114
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.104, 1.05
No. of reflections	2510
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2ⁱ	0.93	2.54	3.271 (4)	136

Symmetry code: (i) x, −y+1/2, z+1/2.

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomas, T. & Thomas, T. J. (2003). J. Cell. Mol. Med. 7, 113–126. Web of Science CrossRef PubMed CAS Google Scholar

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doi:10.1107/S1600536809036022

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N,N′-Bis(2-cyano­ethyl)-4,4′-di­methyl-N,N′-(butane-1,4-di­yl)di­benzene­sulfonamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N,N′-Bis(2-cyanoethyl)-4,4′-dimethyl-N,N′-(butane-1,4-diyl)dibenzenesulfonamide