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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o1983
https://doi.org/10.1107/S1600536812024324

N,N′-{[Ethane-1,2-diylbis(­­oxy)]bis­­(ethane-2,1-di­yl)}bis­­(4-methyl­benzene­sulfonamide)

Nassir N. Al-Mohammed,a Yatimah Alias,a Zanariah Abdullaha and Hamid Khaledia*

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: hamid.khaledi@gmail.com

(Received 23 May 2012; accepted 28 May 2012; online 2 June 2012)

The asymmetric unit of the title compound, C20H28N2O6S2, contains one half-mol­ecule, related to the other half by a twofold rotation axis. The two aromatic rings of the mol­ecule make a dihedral angle of 50.91 (7)°. The O—CH2—CH2—O and N—CH2—CH2—O fragments both adopt gauche conformations, with torsion angles of 76.0 (4) and 70.4 (3)°, respectively. In the crystal, adjacent mol­ecules are linked through N—H⋯O hydrogen bonds into chains along the a-axis direction. The chains are further connected via C—H⋯O inter­actions into a two-dimensional supra­molecular network in the ac plane.

Related literature

For similar structures, see: Polyakova et al. (1990[Polyakova, I. N., Starikova, Z. A. & Tsirkina, O. A. (1990). Kristallografiya, 35, 1284-1287.]); Ding et al. (2003[Ding, X., Ukaji, Y., Fujinami, S. & Inomata, K. (2003). Chem. Lett. 32, 582-583.]).

[Scheme 1]

Experimental

Crystal data

  • C20H28N2O6S2

  • Mr = 456.56

  • Monoclinic, C 2/c

  • a = 11.135 (7) Å

  • b = 9.220 (6) Å

  • c = 21.452 (15) Å

  • β = 93.680 (12)°

  • V = 2198 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 296 K

  • 0.23 × 0.14 × 0.04 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.938, Tmax = 0.989

  • 5135 measured reflections

  • 1983 independent reflections

  • 1558 reflections with I > 2σ(I)

  • Rint = 0.055
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.150

  • S = 1.03

  • 1983 reflections

  • 140 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O2i 0.82 (2) 2.14 (2) 2.944 (3) 171 (3)
C6—H6⋯O1ii 0.93 2.56 3.311 (4) 138
Symmetry codes: (i) [-x+1, y, -z+{\script{3\over 2}}]; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812024324/pv2551sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024324/pv2551Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024324/pv2551Isup3.cml

checkCIF report


Comment top

The title compound (Fig. 1) was obtained through the condensation reaction of 1,8-diamino-3,6-dioxaoctane with p-toluenesulfonyl chloride. A twofold rotation axis passes through the mid-point of C10—C10' bond (symmetry code: ' = -x + 2, y, -z + 3/2), the asymmetric unit therefore comprises one half of the molecule. The two symmetry related aromatic rings in the molecule make a dihedral angle of 50.91 (7)°. Similar to what was observed in a related structure (Polyakova et al., 1990), the O—CH2—CH2—O and N—CH2—CH2—O fragments adopt the gauche conformations with torsion angles of 76.0 (4) and 70.4 (3)° respectively. The S—O bond distances [1.423 (2) and 1.433 (2) Å] and S—N bond distance [1.608 (2) Å] are comparable to the values found in the literature (Ding et al., 2003; Polyakova et al., 1990). The crystal packing of the molecule shows layers in the ac plane formed by N—H···O and C—H···O interactions (Table 1, Fig. 2)

Related literature top

For similar structures, see: Polyakova et al. (1990); Ding et al. (2003).

Experimental top

A solution of p-toluenesulfonyl chloride (2.83 g, 1.48 mmol) in dry dichloromethane (25 ml) was added drop wise to a dichloromethane solution (25 ml) of 1,8-diamino-3,6-dioxaoctane (1 g, 0.675 mmol) and triethylamine (2.34 ml, 1.69 mmol) at 273 K. The mixture was stirred at room temperature overnight, washed with water and saturated solution of NaHCO3 (3 x 10 ml) and dried over MgSO4. The organic layer was evaporated and the residue was dissolved in methanol. The colorless crystals of the title compound were obtained through slow evaporation of the methanolic solution at room temperature (m.p. = 361–363 K).

Refinement top

C-bound hydrogen atoms were located at the calculated positions and refined in riding mode with C—H distances of 0.93 (aryl), 0.96 (methyl) and 0.97 (methylene) Å. The amino hydrogen atom was found in a difference Fourier map and refined with a distance restraint of N—H 0.86 (2) Å. For H atoms, Uiso(H) were set to 1.2 (1.5 for methyl) Ueq(carrier atoms).

Structure description top

The title compound (Fig. 1) was obtained through the condensation reaction of 1,8-diamino-3,6-dioxaoctane with p-toluenesulfonyl chloride. A twofold rotation axis passes through the mid-point of C10—C10' bond (symmetry code: ' = -x + 2, y, -z + 3/2), the asymmetric unit therefore comprises one half of the molecule. The two symmetry related aromatic rings in the molecule make a dihedral angle of 50.91 (7)°. Similar to what was observed in a related structure (Polyakova et al., 1990), the O—CH2—CH2—O and N—CH2—CH2—O fragments adopt the gauche conformations with torsion angles of 76.0 (4) and 70.4 (3)° respectively. The S—O bond distances [1.423 (2) and 1.433 (2) Å] and S—N bond distance [1.608 (2) Å] are comparable to the values found in the literature (Ding et al., 2003; Polyakova et al., 1990). The crystal packing of the molecule shows layers in the ac plane formed by N—H···O and C—H···O interactions (Table 1, Fig. 2)

For similar structures, see: Polyakova et al. (1990); Ding et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: ' = -x + 2, y, -z + 3/2.
[Figure 2] Fig. 2. The 2-D array in the ac plane formed by N—H···O and C—H···O hydrogen bonds, depicted as dashed lines.
N,N'-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4- methylbenzenesulfonamide) top
Crystal data top
C20H28N2O6S2F(000) = 968
Mr = 456.56Dx = 1.380 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1589 reflections
a = 11.135 (7) Åθ = 2.9–25.7°
b = 9.220 (6) ŵ = 0.28 mm−1
c = 21.452 (15) ÅT = 296 K
β = 93.680 (12)°Plate, colorless
V = 2198 (3) Å30.23 × 0.14 × 0.04 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		1983 independent reflections
Radiation source: fine-focus sealed tube1558 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
φ and ω scansθmax = 25.3°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→12
Tmin = 0.938, Tmax = 0.989k = −11→11
5135 measured reflectionsl = −17→25
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0846P)2 + 0.5056P]
where P = (Fo2 + 2Fc2)/3
1983 reflections(Δ/σ)max = 0.001
140 parametersΔρmax = 0.32 e Å−3
1 restraintΔρmin = −0.36 e Å−3
Crystal data top
C20H28N2O6S2V = 2198 (3) Å3
Mr = 456.56Z = 4
Monoclinic, C2/cMo Kα radiation
a = 11.135 (7) ŵ = 0.28 mm−1
b = 9.220 (6) ÅT = 296 K
c = 21.452 (15) Å0.23 × 0.14 × 0.04 mm
β = 93.680 (12)°
Data collection top
Bruker APEXII CCD
diffractometer		1983 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1558 reflections with I > 2σ(I)
Tmin = 0.938, Tmax = 0.989Rint = 0.055
5135 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0531 restraint
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.32 e Å−3
1983 reflectionsΔρmin = −0.36 e Å−3
140 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
xyzUiso*/Ueq
S10.51163 (5)0.03617 (7)0.64470 (3)0.0440 (3)
O10.48265 (19)−0.0655 (2)0.59612 (9)0.0590 (6)
O20.41953 (16)0.0823 (2)0.68398 (9)0.0561 (5)
O30.87638 (18)0.0318 (2)0.72055 (10)0.0567 (6)
N10.6163 (2)−0.0329 (2)0.69058 (11)0.0464 (6)
H10.614 (3)0.002 (3)0.7255 (9)0.056*
C10.7115 (3)0.5726 (4)0.52722 (19)0.0769 (10)
H1A0.73140.64300.55920.115*
H1B0.65280.61260.49730.115*
H1C0.78270.54730.50660.115*
C20.6609 (2)0.4389 (3)0.55625 (15)0.0518 (7)
C30.6610 (2)0.4248 (3)0.62001 (15)0.0533 (7)
H30.69330.49920.64520.064*
C40.6151 (2)0.3047 (3)0.64781 (13)0.0488 (7)
H40.61530.29800.69110.059*
C50.5681 (2)0.1927 (3)0.60972 (12)0.0398 (6)
C60.5678 (2)0.2038 (3)0.54560 (13)0.0512 (7)
H60.53740.12880.52020.061*
C70.6131 (3)0.3270 (3)0.51958 (14)0.0594 (8)
H70.61160.33520.47630.071*
C80.7215 (3)−0.1019 (3)0.66646 (15)0.0578 (8)
H8A0.6986−0.14260.62570.069*
H8B0.7461−0.18160.69390.069*
C90.8272 (3)−0.0037 (4)0.66034 (14)0.0566 (8)
H9A0.8873−0.05180.63690.068*
H9B0.80190.08390.63810.068*
C100.9623 (3)0.1465 (3)0.72024 (14)0.0570 (8)
H10A0.92100.23870.71500.068*
H10B1.01290.13380.68550.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0341 (4)0.0516 (4)0.0450 (4)−0.0066 (3)−0.0080 (3)0.0044 (3)
O10.0642 (13)0.0572 (11)0.0529 (12)−0.0192 (10)−0.0164 (10)−0.0014 (9)
O20.0341 (10)0.0774 (13)0.0567 (12)−0.0015 (9)0.0011 (9)0.0128 (10)
O30.0480 (11)0.0616 (12)0.0595 (13)−0.0071 (9)−0.0041 (10)0.0074 (10)
N10.0402 (12)0.0549 (14)0.0428 (13)0.0016 (10)−0.0072 (11)−0.0002 (10)
C10.067 (2)0.0605 (18)0.102 (3)−0.0117 (17)−0.004 (2)0.0204 (19)
C20.0369 (14)0.0502 (15)0.068 (2)0.0001 (12)−0.0021 (14)0.0101 (14)
C30.0412 (14)0.0467 (14)0.071 (2)−0.0039 (12)−0.0036 (14)−0.0096 (14)
C40.0417 (14)0.0558 (15)0.0478 (16)−0.0024 (12)−0.0043 (12)−0.0049 (13)
C50.0296 (12)0.0452 (13)0.0440 (14)0.0015 (10)−0.0033 (11)0.0013 (11)
C60.0518 (16)0.0545 (15)0.0463 (16)−0.0087 (13)−0.0055 (13)−0.0009 (13)
C70.0644 (19)0.0631 (18)0.0499 (17)−0.0079 (15)−0.0023 (15)0.0103 (14)
C80.0500 (16)0.0562 (16)0.0658 (19)0.0092 (13)−0.0086 (15)−0.0111 (15)
C90.0423 (15)0.0745 (19)0.0526 (18)0.0121 (14)−0.0004 (14)−0.0021 (15)
C100.0504 (16)0.0494 (15)0.071 (2)0.0000 (13)0.0026 (14)0.0071 (14)
Geometric parameters (Å, º) top
S1—O11.423 (2)C3—H30.9300
S1—O21.433 (2)C4—C51.398 (4)
S1—N11.608 (2)C4—H40.9300
S1—C51.761 (3)C5—C61.379 (4)
O3—C91.409 (3)C6—C71.376 (4)
O3—C101.426 (3)C6—H60.9300
N1—C81.457 (4)C7—H70.9300
N1—H10.816 (17)C8—C91.497 (4)
C1—C21.507 (4)C8—H8A0.9700
C1—H1A0.9600C8—H8B0.9700
C1—H1B0.9600C9—H9A0.9700
C1—H1C0.9600C9—H9B0.9700
C2—C31.374 (4)C10—C10i1.482 (6)
C2—C71.383 (4)C10—H10A0.9700
C3—C41.372 (4)C10—H10B0.9700
O1—S1—O2119.26 (13)C6—C5—S1120.5 (2)
O1—S1—N1108.00 (13)C4—C5—S1119.1 (2)
O2—S1—N1106.01 (13)C7—C6—C5119.2 (3)
O1—S1—C5107.33 (13)C7—C6—H6120.4
O2—S1—C5107.22 (13)C5—C6—H6120.4
N1—S1—C5108.68 (12)C6—C7—C2121.5 (3)
C9—O3—C10112.9 (2)C6—C7—H7119.2
C8—N1—S1121.6 (2)C2—C7—H7119.2
C8—N1—H1124 (2)N1—C8—C9114.9 (2)
S1—N1—H1110 (2)N1—C8—H8A108.5
C2—C1—H1A109.5C9—C8—H8A108.5
C2—C1—H1B109.5N1—C8—H8B108.5
H1A—C1—H1B109.5C9—C8—H8B108.5
C2—C1—H1C109.5H8A—C8—H8B107.5
H1A—C1—H1C109.5O3—C9—C8108.8 (2)
H1B—C1—H1C109.5O3—C9—H9A109.9
C3—C2—C7118.2 (3)C8—C9—H9A109.9
C3—C2—C1120.8 (3)O3—C9—H9B109.9
C7—C2—C1121.0 (3)C8—C9—H9B109.9
C4—C3—C2122.2 (3)H9A—C9—H9B108.3
C4—C3—H3118.9O3—C10—C10i109.8 (2)
C2—C3—H3118.9O3—C10—H10A109.7
C3—C4—C5118.6 (3)C10i—C10—H10A109.7
C3—C4—H4120.7O3—C10—H10B109.7
C5—C4—H4120.7C10i—C10—H10B109.7
C6—C5—C4120.3 (2)H10A—C10—H10B108.2
Symmetry code: (i) −x+2, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2ii0.82 (2)2.14 (2)2.944 (3)171 (3)
C6—H6···O1iii0.932.563.311 (4)138
Symmetry codes: (ii) −x+1, y, −z+3/2; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC20H28N2O6S2
Mr456.56
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)11.135 (7), 9.220 (6), 21.452 (15)
β (°) 93.680 (12)
V (Å3)2198 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.28
Crystal size (mm)0.23 × 0.14 × 0.04
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.938, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		5135, 1983, 1558
Rint0.055
(sin θ/λ)max (Å−1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.150, 1.03
No. of reflections1983
No. of parameters140
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.32, −0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.816 (17)2.135 (18)2.944 (3)171 (3)
C6—H6···O1ii0.932.563.311 (4)138.2
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y, −z+1.
 

Acknowledgements

The authors thank the University of Malaya for funding this study (HIR MOHE (Fakulti) F0004–21001).

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDing, X., Ukaji, Y., Fujinami, S. & Inomata, K. (2003). Chem. Lett. 32, 582–583.  Web of Science CSD CrossRef CAS Google Scholar
 First citationPolyakova, I. N., Starikova, Z. A. & Tsirkina, O. A. (1990). Kristallografiya, 35, 1284–1287.  CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o1983
https://doi.org/10.1107/S1600536812024324
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