![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
N,N′-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4-methylbenzenesulfonamide)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: hamid.khaledi@gmail.com
The 20H28N2O6S2, 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.
of the title compound, CExperimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007
); data reduction: SAINT; 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 and publCIF (Westrip, 2010
).
Supporting information
https://doi.org/10.1107/S1600536812024324/pv2551sup1.cif
contains datablocks I, global. DOI: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
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
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).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).
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
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).
Data collection: APEX2 (Bruker, 2007); cell
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).C20H28N2O6S2 | F(000) = 968 |
Mr = 456.56 | Dx = 1.380 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1589 reflections |
a = 11.135 (7) Å | θ = 2.9–25.7° |
b = 9.220 (6) Å | µ = 0.28 mm−1 |
c = 21.452 (15) Å | T = 296 K |
β = 93.680 (12)° | Plate, colorless |
V = 2198 (3) Å3 | 0.23 × 0.14 × 0.04 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 1983 independent reflections |
Radiation source: fine-focus sealed tube | 1558 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
φ and ω scans | θmax = 25.3°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→12 |
Tmin = 0.938, Tmax = 0.989 | k = −11→11 |
5135 measured reflections | l = −17→25 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H 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 parameters | Δρmax = 0.32 e Å−3 |
1 restraint | Δρmin = −0.36 e Å−3 |
C20H28N2O6S2 | V = 2198 (3) Å3 |
Mr = 456.56 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.135 (7) Å | µ = 0.28 mm−1 |
b = 9.220 (6) Å | T = 296 K |
c = 21.452 (15) Å | 0.23 × 0.14 × 0.04 mm |
β = 93.680 (12)° |
Bruker APEXII CCD diffractometer | 1983 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1558 reflections with I > 2σ(I) |
Tmin = 0.938, Tmax = 0.989 | Rint = 0.055 |
5135 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 1 restraint |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.32 e Å−3 |
1983 reflections | Δρmin = −0.36 e Å−3 |
140 parameters |
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 | Uiso*/Ueq | ||
S1 | 0.51163 (5) | 0.03617 (7) | 0.64470 (3) | 0.0440 (3) | |
O1 | 0.48265 (19) | −0.0655 (2) | 0.59612 (9) | 0.0590 (6) | |
O2 | 0.41953 (16) | 0.0823 (2) | 0.68398 (9) | 0.0561 (5) | |
O3 | 0.87638 (18) | 0.0318 (2) | 0.72055 (10) | 0.0567 (6) | |
N1 | 0.6163 (2) | −0.0329 (2) | 0.69058 (11) | 0.0464 (6) | |
H1 | 0.614 (3) | 0.002 (3) | 0.7255 (9) | 0.056* | |
C1 | 0.7115 (3) | 0.5726 (4) | 0.52722 (19) | 0.0769 (10) | |
H1A | 0.7314 | 0.6430 | 0.5592 | 0.115* | |
H1B | 0.6528 | 0.6126 | 0.4973 | 0.115* | |
H1C | 0.7827 | 0.5473 | 0.5066 | 0.115* | |
C2 | 0.6609 (2) | 0.4389 (3) | 0.55625 (15) | 0.0518 (7) | |
C3 | 0.6610 (2) | 0.4248 (3) | 0.62001 (15) | 0.0533 (7) | |
H3 | 0.6933 | 0.4992 | 0.6452 | 0.064* | |
C4 | 0.6151 (2) | 0.3047 (3) | 0.64781 (13) | 0.0488 (7) | |
H4 | 0.6153 | 0.2980 | 0.6911 | 0.059* | |
C5 | 0.5681 (2) | 0.1927 (3) | 0.60972 (12) | 0.0398 (6) | |
C6 | 0.5678 (2) | 0.2038 (3) | 0.54560 (13) | 0.0512 (7) | |
H6 | 0.5374 | 0.1288 | 0.5202 | 0.061* | |
C7 | 0.6131 (3) | 0.3270 (3) | 0.51958 (14) | 0.0594 (8) | |
H7 | 0.6116 | 0.3352 | 0.4763 | 0.071* | |
C8 | 0.7215 (3) | −0.1019 (3) | 0.66646 (15) | 0.0578 (8) | |
H8A | 0.6986 | −0.1426 | 0.6257 | 0.069* | |
H8B | 0.7461 | −0.1816 | 0.6939 | 0.069* | |
C9 | 0.8272 (3) | −0.0037 (4) | 0.66034 (14) | 0.0566 (8) | |
H9A | 0.8873 | −0.0518 | 0.6369 | 0.068* | |
H9B | 0.8019 | 0.0839 | 0.6381 | 0.068* | |
C10 | 0.9623 (3) | 0.1465 (3) | 0.72024 (14) | 0.0570 (8) | |
H10A | 0.9210 | 0.2387 | 0.7150 | 0.068* | |
H10B | 1.0129 | 0.1338 | 0.6855 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0341 (4) | 0.0516 (4) | 0.0450 (4) | −0.0066 (3) | −0.0080 (3) | 0.0044 (3) |
O1 | 0.0642 (13) | 0.0572 (11) | 0.0529 (12) | −0.0192 (10) | −0.0164 (10) | −0.0014 (9) |
O2 | 0.0341 (10) | 0.0774 (13) | 0.0567 (12) | −0.0015 (9) | 0.0011 (9) | 0.0128 (10) |
O3 | 0.0480 (11) | 0.0616 (12) | 0.0595 (13) | −0.0071 (9) | −0.0041 (10) | 0.0074 (10) |
N1 | 0.0402 (12) | 0.0549 (14) | 0.0428 (13) | 0.0016 (10) | −0.0072 (11) | −0.0002 (10) |
C1 | 0.067 (2) | 0.0605 (18) | 0.102 (3) | −0.0117 (17) | −0.004 (2) | 0.0204 (19) |
C2 | 0.0369 (14) | 0.0502 (15) | 0.068 (2) | 0.0001 (12) | −0.0021 (14) | 0.0101 (14) |
C3 | 0.0412 (14) | 0.0467 (14) | 0.071 (2) | −0.0039 (12) | −0.0036 (14) | −0.0096 (14) |
C4 | 0.0417 (14) | 0.0558 (15) | 0.0478 (16) | −0.0024 (12) | −0.0043 (12) | −0.0049 (13) |
C5 | 0.0296 (12) | 0.0452 (13) | 0.0440 (14) | 0.0015 (10) | −0.0033 (11) | 0.0013 (11) |
C6 | 0.0518 (16) | 0.0545 (15) | 0.0463 (16) | −0.0087 (13) | −0.0055 (13) | −0.0009 (13) |
C7 | 0.0644 (19) | 0.0631 (18) | 0.0499 (17) | −0.0079 (15) | −0.0023 (15) | 0.0103 (14) |
C8 | 0.0500 (16) | 0.0562 (16) | 0.0658 (19) | 0.0092 (13) | −0.0086 (15) | −0.0111 (15) |
C9 | 0.0423 (15) | 0.0745 (19) | 0.0526 (18) | 0.0121 (14) | −0.0004 (14) | −0.0021 (15) |
C10 | 0.0504 (16) | 0.0494 (15) | 0.071 (2) | 0.0000 (13) | 0.0026 (14) | 0.0071 (14) |
S1—O1 | 1.423 (2) | C3—H3 | 0.9300 |
S1—O2 | 1.433 (2) | C4—C5 | 1.398 (4) |
S1—N1 | 1.608 (2) | C4—H4 | 0.9300 |
S1—C5 | 1.761 (3) | C5—C6 | 1.379 (4) |
O3—C9 | 1.409 (3) | C6—C7 | 1.376 (4) |
O3—C10 | 1.426 (3) | C6—H6 | 0.9300 |
N1—C8 | 1.457 (4) | C7—H7 | 0.9300 |
N1—H1 | 0.816 (17) | C8—C9 | 1.497 (4) |
C1—C2 | 1.507 (4) | C8—H8A | 0.9700 |
C1—H1A | 0.9600 | C8—H8B | 0.9700 |
C1—H1B | 0.9600 | C9—H9A | 0.9700 |
C1—H1C | 0.9600 | C9—H9B | 0.9700 |
C2—C3 | 1.374 (4) | C10—C10i | 1.482 (6) |
C2—C7 | 1.383 (4) | C10—H10A | 0.9700 |
C3—C4 | 1.372 (4) | C10—H10B | 0.9700 |
O1—S1—O2 | 119.26 (13) | C6—C5—S1 | 120.5 (2) |
O1—S1—N1 | 108.00 (13) | C4—C5—S1 | 119.1 (2) |
O2—S1—N1 | 106.01 (13) | C7—C6—C5 | 119.2 (3) |
O1—S1—C5 | 107.33 (13) | C7—C6—H6 | 120.4 |
O2—S1—C5 | 107.22 (13) | C5—C6—H6 | 120.4 |
N1—S1—C5 | 108.68 (12) | C6—C7—C2 | 121.5 (3) |
C9—O3—C10 | 112.9 (2) | C6—C7—H7 | 119.2 |
C8—N1—S1 | 121.6 (2) | C2—C7—H7 | 119.2 |
C8—N1—H1 | 124 (2) | N1—C8—C9 | 114.9 (2) |
S1—N1—H1 | 110 (2) | N1—C8—H8A | 108.5 |
C2—C1—H1A | 109.5 | C9—C8—H8A | 108.5 |
C2—C1—H1B | 109.5 | N1—C8—H8B | 108.5 |
H1A—C1—H1B | 109.5 | C9—C8—H8B | 108.5 |
C2—C1—H1C | 109.5 | H8A—C8—H8B | 107.5 |
H1A—C1—H1C | 109.5 | O3—C9—C8 | 108.8 (2) |
H1B—C1—H1C | 109.5 | O3—C9—H9A | 109.9 |
C3—C2—C7 | 118.2 (3) | C8—C9—H9A | 109.9 |
C3—C2—C1 | 120.8 (3) | O3—C9—H9B | 109.9 |
C7—C2—C1 | 121.0 (3) | C8—C9—H9B | 109.9 |
C4—C3—C2 | 122.2 (3) | H9A—C9—H9B | 108.3 |
C4—C3—H3 | 118.9 | O3—C10—C10i | 109.8 (2) |
C2—C3—H3 | 118.9 | O3—C10—H10A | 109.7 |
C3—C4—C5 | 118.6 (3) | C10i—C10—H10A | 109.7 |
C3—C4—H4 | 120.7 | O3—C10—H10B | 109.7 |
C5—C4—H4 | 120.7 | C10i—C10—H10B | 109.7 |
C6—C5—C4 | 120.3 (2) | H10A—C10—H10B | 108.2 |
Symmetry code: (i) −x+2, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2ii | 0.82 (2) | 2.14 (2) | 2.944 (3) | 171 (3) |
C6—H6···O1iii | 0.93 | 2.56 | 3.311 (4) | 138 |
Symmetry codes: (ii) −x+1, y, −z+3/2; (iii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H28N2O6S2 |
Mr | 456.56 |
Crystal system, space group | Monoclinic, 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) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.23 × 0.14 × 0.04 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.938, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5135, 1983, 1558 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.150, 1.03 |
No. of reflections | 1983 |
No. of parameters | 140 |
No. of restraints | 1 |
H-atom treatment | H 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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.816 (17) | 2.135 (18) | 2.944 (3) | 171 (3) |
C6—H6···O1ii | 0.93 | 2.56 | 3.311 (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
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ding, X., Ukaji, Y., Fujinami, S. & Inomata, K. (2003). Chem. Lett. 32, 582–583. Web of Science CSD CrossRef CAS Google Scholar
Polyakova, I. N., Starikova, Z. A. & Tsirkina, O. A. (1990). Kristallografiya, 35, 1284–1287. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, 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.
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)