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Acta Cryst. (2009). E65, o2433    [ doi:10.1107/S1600536809036022 ]

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

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

Abstract top

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.

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%).

Refinement top

The H atoms were geometrically placed (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

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
[Figure 1] 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).
[Figure 2] 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
C24H30N4O4S2F(000) = 532
Mr = 502.64Dx = 1.303 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2757 reflections
a = 16.688 (13) Åθ = 3.0–27.6°
b = 5.786 (5) ŵ = 0.25 mm−1
c = 13.675 (11) ÅT = 296 K
β = 104.005 (13)°Rod, colorless
V = 1281.3 (17) Å30.34 × 0.26 × 0.21 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer		2510 independent reflections
Radiation source: fine-focus sealed tube2114 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		h = −16→20
Tmin = 0.921, Tmax = 0.950k = −7→7
6684 measured reflectionsl = −16→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0583P)2 + 0.2525P]
where P = (Fo2 + 2Fc2)/3
2510 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C24H30N4O4S2V = 1281.3 (17) Å3
Mr = 502.64Z = 2
Monoclinic, P21/cMo Kα radiation
a = 16.688 (13) ŵ = 0.25 mm−1
b = 5.786 (5) ÅT = 296 K
c = 13.675 (11) Å0.34 × 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)
Tmin = 0.921, Tmax = 0.950Rint = 0.019
6684 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.104Δρmax = 0.20 e Å−3
S = 1.05Δρmin = −0.28 e Å−3
2510 reflectionsAbsolute structure: ?
155 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
S10.24666 (2)0.32320 (7)0.53380 (3)0.03878 (15)
O10.20256 (7)0.1573 (2)0.57929 (10)0.0506 (3)
O20.30224 (8)0.2415 (2)0.47571 (10)0.0558 (3)
N10.17969 (8)0.4914 (2)0.46127 (10)0.0392 (3)
N20.09678 (12)0.0954 (3)0.26259 (14)0.0718 (5)
C10.30449 (9)0.4988 (3)0.63262 (12)0.0371 (4)
C20.33821 (10)0.7065 (3)0.61032 (13)0.0469 (4)
H2A0.32750.75920.54420.056*
C30.38797 (11)0.8344 (3)0.68757 (15)0.0532 (5)
H3A0.41080.97270.67250.064*
C40.40431 (10)0.7595 (4)0.78710 (14)0.0496 (4)
C50.36879 (11)0.5538 (4)0.80728 (13)0.0541 (5)
H5A0.37870.50200.87350.065*
C60.31883 (11)0.4232 (3)0.73143 (13)0.0498 (4)
H6A0.29520.28650.74680.060*
C70.45863 (13)0.8996 (4)0.87086 (16)0.0720 (6)
H7A0.48391.02330.84230.108*
H7B0.50080.80200.91030.108*
H7C0.42570.96250.91310.108*
C80.03371 (9)0.4433 (3)0.47933 (13)0.0450 (4)
H8A0.01440.42540.40690.054*
H8B0.04550.29080.50870.054*
C90.11282 (9)0.5880 (3)0.50313 (12)0.0429 (4)
H9A0.09990.74250.47650.052*
H9B0.13260.60080.57570.052*
C100.19632 (11)0.5953 (3)0.37044 (13)0.0469 (4)
H10A0.24930.54070.36220.056*
H10B0.19970.76180.37850.056*
C110.12903 (12)0.5356 (3)0.27550 (12)0.0497 (4)
H11A0.07880.61830.27720.060*
H11B0.14660.58680.21640.060*
C120.11145 (12)0.2864 (4)0.26701 (13)0.0499 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0360 (2)0.0370 (3)0.0428 (2)0.00198 (15)0.00858 (17)−0.00311 (16)
O10.0517 (7)0.0410 (7)0.0564 (7)−0.0076 (5)0.0077 (6)0.0045 (5)
O20.0506 (7)0.0601 (8)0.0597 (7)0.0117 (6)0.0191 (6)−0.0116 (7)
N10.0341 (7)0.0462 (8)0.0371 (7)0.0025 (6)0.0086 (5)−0.0004 (6)
N20.0825 (13)0.0529 (11)0.0736 (12)−0.0051 (10)0.0062 (10)−0.0087 (9)
C10.0296 (7)0.0394 (9)0.0420 (8)0.0018 (6)0.0080 (6)−0.0010 (7)
C20.0475 (9)0.0444 (10)0.0470 (9)−0.0020 (8)0.0075 (8)0.0057 (8)
C30.0520 (10)0.0429 (10)0.0627 (12)−0.0099 (8)0.0100 (9)−0.0004 (8)
C40.0377 (9)0.0570 (11)0.0531 (10)−0.0020 (8)0.0092 (8)−0.0103 (9)
C50.0539 (10)0.0667 (13)0.0400 (9)−0.0098 (9)0.0078 (8)−0.0006 (9)
C60.0490 (10)0.0542 (11)0.0464 (9)−0.0109 (8)0.0118 (8)0.0035 (8)
C70.0594 (12)0.0813 (16)0.0688 (14)−0.0156 (11)0.0033 (10)−0.0215 (12)
C80.0369 (8)0.0532 (11)0.0440 (9)0.0028 (8)0.0078 (7)−0.0079 (8)
C90.0371 (8)0.0465 (10)0.0441 (9)0.0045 (7)0.0077 (7)−0.0060 (8)
C100.0493 (10)0.0462 (10)0.0465 (9)−0.0050 (8)0.0140 (8)0.0028 (8)
C110.0633 (11)0.0454 (10)0.0388 (9)0.0042 (8)0.0092 (8)0.0056 (7)
C120.0549 (11)0.0527 (12)0.0395 (9)0.0032 (9)0.0062 (8)−0.0036 (8)
Geometric parameters (Å, °) top
S1—O11.4392 (14)C6—H6A0.9300
S1—O21.4393 (14)C7—H7A0.9600
S1—N11.6259 (15)C7—H7B0.9600
S1—C11.7772 (18)C7—H7C0.9600
N1—C101.466 (2)C8—C8i1.524 (3)
N1—C91.481 (2)C8—C91.530 (2)
N2—C121.130 (3)C8—H8A0.9700
C1—C61.385 (2)C8—H8B0.9700
C1—C21.392 (2)C9—H9A0.9700
C2—C31.389 (3)C9—H9B0.9700
C2—H2A0.9300C10—C111.536 (2)
C3—C41.391 (3)C10—H10A0.9700
C3—H3A0.9300C10—H10B0.9700
C4—C51.387 (3)C11—C121.471 (3)
C4—C71.513 (3)C11—H11A0.9700
C5—C61.387 (3)C11—H11B0.9700
C5—H5A0.9300
O1—S1—O2118.99 (9)H7A—C7—H7B109.5
O1—S1—N1108.36 (9)C4—C7—H7C109.5
O2—S1—N1107.44 (9)H7A—C7—H7C109.5
O1—S1—C1107.02 (9)H7B—C7—H7C109.5
O2—S1—C1107.68 (9)C8i—C8—C9111.23 (18)
N1—S1—C1106.75 (9)C8i—C8—H8A109.4
C10—N1—C9119.19 (14)C9—C8—H8A109.4
C10—N1—S1121.28 (12)C8i—C8—H8B109.4
C9—N1—S1117.45 (11)C9—C8—H8B109.4
C6—C1—C2120.19 (16)H8A—C8—H8B108.0
C6—C1—S1119.69 (14)N1—C9—C8113.80 (14)
C2—C1—S1120.06 (13)N1—C9—H9A108.8
C3—C2—C1119.52 (17)C8—C9—H9A108.8
C3—C2—H2A120.2N1—C9—H9B108.8
C1—C2—H2A120.2C8—C9—H9B108.8
C2—C3—C4121.16 (18)H9A—C9—H9B107.7
C2—C3—H3A119.4N1—C10—C11111.99 (15)
C4—C3—H3A119.4N1—C10—H10A109.2
C5—C4—C3118.05 (17)C11—C10—H10A109.2
C5—C4—C7121.07 (18)N1—C10—H10B109.2
C3—C4—C7120.88 (19)C11—C10—H10B109.2
C4—C5—C6121.83 (17)H10A—C10—H10B107.9
C4—C5—H5A119.1C12—C11—C10112.22 (15)
C6—C5—H5A119.1C12—C11—H11A109.2
C1—C6—C5119.23 (18)C10—C11—H11A109.2
C1—C6—H6A120.4C12—C11—H11B109.2
C5—C6—H6A120.4C10—C11—H11B109.2
C4—C7—H7A109.5H11A—C11—H11B107.9
C4—C7—H7B109.5N2—C12—C11178.0 (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—C1095.68 (14)C2—C3—C4—C7179.95 (17)
O1—S1—N1—C947.17 (14)C3—C4—C5—C60.5 (3)
O2—S1—N1—C9176.93 (11)C7—C4—C5—C6179.98 (18)
C1—S1—N1—C9−67.79 (13)C2—C1—C6—C5−1.6 (3)
O1—S1—C1—C617.62 (16)S1—C1—C6—C5175.56 (13)
O2—S1—C1—C6−111.40 (15)C4—C5—C6—C10.6 (3)
N1—S1—C1—C6133.48 (14)C10—N1—C9—C8102.87 (18)
O1—S1—C1—C2−165.17 (13)S1—N1—C9—C8−93.29 (15)
O2—S1—C1—C265.80 (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—C31.6 (3)S1—N1—C10—C11123.77 (15)
S1—C1—C2—C3−175.62 (13)N1—C10—C11—C12−50.0 (2)
Symmetry codes: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O2ii0.932.543.271 (4)136
Symmetry codes: (ii) x, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O2i0.932.543.271 (4)136
Symmetry codes: (i) x, −y+1/2, z+1/2.
references
References top

Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Thomas, T. & Thomas, T. J. (2003). J. Cell. Mol. Med. 7, 113–126.